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Indole derivatives as agrochemicals:An overview

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Chinese Chemical Letters 2024年第7期35卷 66-72页

作者： Ping Sun Yuanqin Huang Shunhong Chen Xining Ma Zhaokai Yang Jian Wu National key laboratory of green pesticide Key Laboratory of Green Pesticide and Agricultural BioengineeringMinistry of EducationGuizhou UniversityGuiyang 550025China

Indole is a biologically active compound formed by the fusion of benzene and pyrrole,and it is widely found in natural products and *** to the unique structure and properties of indole,its derivatives often exhibit distinctive physiological activities,which has led to widespread attention in the field of pesticide *** the design strategies and structure-activity relationships(SARs)of compounds is a crucial step in developing novel *** review mainly summarizes indole compounds with plant growth regulating,antiviral,fungicidal,herbicidal,and insecticidal activities,with the aim of providing new insights into the discovery and mechanism of action of novel indole-based pesticides.

关键词： Indole compounds Agrochemicals Biological activity Structure-activity relationship Mechanism of action

Carbene-catalyzed enantioselective seleno-Michael addition as access to antimicrobial active Se-containing heterocycles

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Science China Chemistry 2024年第7期67卷 2199-2205页

作者： Hongyan Long Sha Zhao Chunyan Jian Xiuli Wu Fengfei Lu Minghong Liao Fengrui Che Xingxing Wu Yonggui Robin Chi state key laboratory of green pesticide Key Laboratory of Green Pesticide and Agricultural BioengineeringMinistry of EducationGuizhou UniversityGuiyang 550025China School of Chemistry Chemical Engineeringand BiotechnologyNanyang Technological UniversitySingapore 637371Singapore

Organoseleniums exhibit a diverse set of biological activities that are pivotal for drug discovery and are widely explored in synthetic chemistry and material *** many transformations have been developed for non-enantioselective C–Se bond formations,the catalyst-controlled stereoselective preparation of chiral organoseleniums continues to be of considerable *** particular,there are limited studies on the enantioselective seleno-Michael addition reactions to access chiral selenium functional ***,we disclose a carbene-catalyzed highly enantioselective nucleophilic C–Se bond construction through formal[3+3]annulations between selenocarboxamides and bromoenals,affording seleno-thiazinone products with good yields and excellent *** choice of a weak inorganic base was pivotal to suppressing the unproductive racemization and decomposition of the selenium ***,the catalytically generated chiral selenium-containing heterocyclic products feature remarkable antimicrobial activities that could serve as promising lead scaffolds for further agrochemical development.

关键词： seleno-Michael addition organocatalysis N-heterocyclic carbene seleno-heterocycles antimicrobial activity

Bactericidal bissulfone B7 targets bacterial pyruvate kinase to impair bacterial biology and pathogenicity in plants

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Science China(Life Sciences) 2024年第2期67卷 391-402页

作者： Awei Zhang Haizhen Zhang Ronghua Wang Hongfu He Baoan Song Runjiang Song National key laboratory of green pesticide Key Laboratory of Green Pesticide and Agricultural BioengineeringMinistry of EducationCenter for R&D of Fine Chemicals of Guizhou UniversityGuiyang 550025China

The prevention and control of rice bacterial leaf blight(BLB)disease has not yet been achieved due to the lack of effective agrochemicals and available ***,we develop a series of novel bissulfones and a novel target with a unique mechanism to address this *** developed bissulfones can control Xanthomonas oryzae ***(Xoo),and 2-(bis(methylsulfonyl)methylene)-N-(4-chlorophenyl)hydrazine-1-carboxamide(B_(7))is more effective than the commercial drugs thiodiazole copper(TC)and bismerthiazol(BT).Pyruvate kinase(PYK)in Xoo has been identified for the first time as the target protein of our bissulfone B_(7).PYK modulates bacterial virulence via a CRP-like protein(Clp)/two-component system regulatory protein(reg R)*** elucidation of this pathway facilitates the use of B_(7)to reduce PYK expression at the transcriptional level,block PYK activity at the protein level,and impair the interaction within the PYK-Clp-reg R complex via competitive inhibition,thereby attenuating bacterial biology and *** study offers insights into the molecular and mechanistic aspects underlying anti-Xoo strategies that target *** believe that these valuable discoveries will be used for bacterial disease control in the future.

关键词： 2-bissulfone-N-phenylhydrazine-1-carboxamide derivatives Xoo antibacterial activities pyruvate kinase regulatory mechanism

Discovery and structure-activity relationship studies of novel tetrahydro-β-carboline derivatives as apoptosis initiators for treating bacterial infections

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Journal of Integrative Agriculture 2024年第4期23卷 1259-1273页

作者： Shanshan Su Hongwu Liu Junrong Zhang Puying Qi Yue Ding Ling Zhang Linli Yang Liwei Liu Xiang Zhou Song Yang National key laboratory of green pesticide/key laboratory of green pesticide and Agricultural Bioengineering Ministry of Education/Center for R&D of Fine ChemicalsGuizhou UniversityGuiyang 550025China

Developing and excavating new agrochemicals with highly active and safe is an important tactic for protecting crop health and food *** this paper,to discover the new bactericide candidates,we designed,prepared a new type of1,2,3,4-tetrahydro-β-carboline(THC)derivatives and evaluated the in vitro and in vivo bioactivities against the Xanthomonas oryzae ***(Xoo),Xanthomonas axonopodis ***(Xac),and Pseudomonas syringae ***(Psa).The in vitro bioassay results exhibited that most title molecules possessed good activity toward the three plant pathogenic bacteria,the compound A17 showed the most active against Xoo and Xac with EC50 values of 7.27 and 4.89 mg mL^(-1)respectively,and compound A8 exhibited the best inhibitory activity against Psa with EC50value of 4.87 mg mL^(-1).Pot experiments showed that compound A17 exhibited excellent in vivo antibacterial activities to manage rice bacterial leaf blight and citrus bacterial canker,with protective efficiencies of 52.67 and 79.79%at 200 mgmL^(-1),***,compound A8 showed good control efficiency(84.31%)against kiwifruit bacterial canker at 200 mg mL^(-1).Antibacterial mechanism suggested that these compounds could interfere with the balance of the redox system,damage the cell membrane,and induce the apoptosis of Xoo *** together,our study revealed that tetrahydro-β-carboline derivatives could be a promising candidate model for novel broadspectrum bactericides.

关键词： tetrahydro-β-carboline derivatives antibacterial activity ROS cell apoptosis

Chiral boryl radical catalyzed asymmetric radical cycloisomerization

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Science China Chemistry 2024年第7期67卷 2121-2123页

作者： Jiamiao Jin Shi-Chao Ren Yonggui Robin Chi National key laboratory of green pesticide Key Laboratory of Green Pesticide and Agricultural BioengineeringMinistry of EducationGuizhou UniversityGuiyang 550025China School of Chemistry Chemical Engineeringand BiotechnologyNanyang Technological UniversitySingapore 637371Singapore

Asymmetric catalytic organic synthesis is of profound importance in modern research and industries,providing optically enriched molecules with diverse structures and functions[1].Enzymes,transition metal complexes,and simple organic molecules have all been found as powerful catalysts that enable the bond breaking and forming events with excellent control over stereo-selectivity *** the realm of designed small molecule organic catalysts.

关键词： radical catalyzed asymmetric

Hydrazone derivatives in agrochemical discovery and development

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Chinese Chemical Letters 2024年第3期35卷 104-113页

作者： Ya Wang Shengxin Guo Lijiao Yu Wei Zhang Zhenchao Wang Yonggui Robin Chi Jian Wu National key laboratory of green pesticide Key Laboratory of Green Pesticide and Agricultural BioengineeringMinistry of EducationGuizhou UniversityHuaxi DistrictGuiyang 550025China Division of Chemistry&Biological Chemistry School of Physical&Mathematical SciencesNanyang Technological UniversitySingapore 637371Singapore

As a common active substructure,hydrazone has attracted increasing attention and is considered essential for pesticide *** has been widely regarded as a potential insecticidal,antibacterial,antifungal,antiviral,and herbicidal *** this review,we highlight the pesticide versatility of hydrazone fragments and provide a comprehensive summary of the biological activity,structure-activity relationship analysis(SARs),and primary mechanism of their *** profile is expected to give valuable information for discovering new pesticides.

关键词： Hydrazone Agrochemicals Biological activity Structure-activity relationship Preliminary mechanism

Host-Induced Gene Silencing of Effector AGLIP1 Enhanced Resistance of Rice to Rhizoctonia solani AG1-IA

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Rice science 2024年第4期31卷 463-474,I0031-I0034页

作者： ZHAO Mei LIU Xiaoxue WAN Jun ZHOU Erxun SHU Canwei pesticide state key laboratory of green pesticide Guangdong Province Key Laboratory of Microbial Signals and Disease ControlCollege of Plant ProtectionSouth China Agricultural UniversityGuangzhou 510642China College of Life Science and Engineering Henan University of Urban ConstructionPingdingshan 467036China

Rice sheath blight, caused by Rhizoctonia solani AG1-IA, is a major disease in rice-growing areas worldwide. Effectors of phytopathogenic fungi play important roles during the infection process of fungal pathogens onto their host plants. However, the molecular mechanisms by which R. solani effectors regulate rice immunity are not well understood. Through prediction, 78 candidate effector molecules were identified. Using the tobacco rattle virus-host induced gene silencing(TRV-HIGS) system, 45 RNAi constructs of effector genes were infiltrated into Nicotiana benthamiana leaves. The results revealed that eight of these constructs resulted in a significant reduction in necrosis caused by infection with the AG1-IA strain GD-118. Additionally, stable rice transformants carrying the double-stranded RNA construct for one of the effector genes, AGLIP1, were generated to further verify the function of this gene. The suppression of the AGLIP1 gene increased the resistance of both N. benthamiana and rice against GD-118, and also affected the growth rate of GD-118, indicating that AGLIP1 is a key pathogenic factor. Small RNA sequencing showed that the HIGS vectors were processed into si RNAs within the plants and then translocated to the fungi, leading to the silencing of the target genes. As a result, AGLIP1 might be an excellent candidate for HIGS, thereby enhancing crop resistance against the pathogen and contributing to the control of R. solani infection.

关键词： Rhizoctonia solani host-induced gene silencing lipase tobacco rattle virus

Lighting up plants with near-infrared fluorescence probes

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Science China Chemistry 2024年第3期67卷 774-787页

作者： Yida Pang Mengjiao Lu Hyeonji Rha Wenchao Yang Amit Sharma Yao Sun Jong Seung Kim National key laboratory of green pesticide Key Laboratory of Green Pesticide and Agricultural BioengineeringMinistry of EducationCenter for R&D of Fine Chemicals of Guizhou UniversityGuiyang 550025China National key laboratory of green pesticide College of ChemistryCentral China Normal UniversityWuhan 430079China Department of Chemistry Korea UniversitySeoul 02841Korea CSIR-Central Scientific Instruments Organisation Sector-30CChandigarh160030India TheranoChem Incorporation Seongbuk-guSeoul02856Korea

Fluorescence imaging is a non-invasive and highly sensitive bioimaging technique that has shown remarkable strides in plant science. It enables real-time monitoring and analysis of biological and pathological processes in plants by labeling specific molecular or cellular structures with fluorescent probes. However, tissue scattering and phytochrome interference have been obstacles for conventional fluorescence imaging of plants in the ultraviolet and visible spectrum, resulting in unsatisfactory imaging quality. Fortunately, advances in near-infrared(NIR) fluorescence imaging technology(650-900 nm) offer superior spatial-temporal resolution and reduced tissue scattering, which is sure to improve plant imaging quality. In this review, we summarize recent progress in the development of NIR fluorescence imaging probes and their applications for in vivo plant imaging and the identification of plant-related biomolecules. We hope this review provides a new perspective for plant science research and highlights NIR fluorescence imaging as a powerful tool for analyzing plant physiology, adaptive mechanisms, and coping with environmental stress in the near future.

关键词： NIR fluorescent probe plant imaging biologic application

Synergy of heterogeneous Co/Ni dual atoms enabling selective C-O bond scission of lignin coupling with in-situ N-functionalization

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Journal of Energy Chemistry 2024年第5期92卷 16-25页

作者： Baoyu Wang Jinshu Huang Hongguo Wu Ximing Yan Yuhe Liao Hu Li National key laboratory of green pesticide Key Laboratory of Green Pesticide&Agricultural BioengineeringMinistry of EducationState-Local Joint Laboratory for Comprehensive Utilization of BiomassCollege of Pharmacy&Center for R&D of Fine ChemicalsGuizhou UniversityGuiyang 550025GuizhouChina Guangxi key laboratory of green Chemical Materials and Safety Technology Beibu Gulf UniversityQinzhou 535011GuangxiChina Guangzhou Institute of Energy Conversion Chinese Academy of SciencesGuangzhou 510640GuangdongChina

Selective cleavage of Csp^(2)-OCH_(3)bond in lignin without breaking other types of C-O bonds followed by N-functionalization is fascinating for on-purpose valorization of ***,a Co/Ni-based dual-atom catalyst CoNiDA@NC prepared by in-situ evaporation and acid-etching of metal species from tailor-made metal–organic frameworks was efficient for reductive upgrading of various lignin-derived phenols to cyclohexanols(88.5%–99.9%yields),which had ca.4 times higher reaction rate than the single-atom catalyst and was superior to state-of-the-art heterogeneous *** synergistic catalysis of Co/Ni dual atoms facilitated both hydrogen dissociation and hydrogenolysis steps,and could optimize adsorption configuration of lignin-derived methoxylated phenols to further favor the Csp^(2)-OCH_(3)cleavage,as elaborated by theoretical ***,the CoNi_(DA)@NC catalyst was highly recyclable,and exhibited excellent demethoxylation performance(77.1%yield)in real lignin monomer *** in-situ cascade conversion processes assisted by dual-atom catalysis,various high-value N-containing chemicals,including caprolactams and cyclohexylamines,could be produced from lignin.

关键词： Biomass conversion Heterogeneous catalysis Lignin Dual-atom catalyst Selective C-ocleavage