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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

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

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N-heterocyclic carbene-catalyzed arene formation reactions

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Science china Chemistry 2022年第2期65卷 210-223页

作者： Tingting Li Zhichao Jin yonggui robin chi State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering Key Laboratory of Green Pesticide and Agricultural BioengineeringMinistry of EducationGuizhou UniversityGuiyang 550025China Division of Chemistry&Biological Chemistry School of Physical&Mathematical SciencesNanyang Technological UniversitySingapore 637371Singapore

N-heterocyclic carbene-catalyzed reactions for the formation of aromatic compounds are *** reactions are subdivided into 4 types based on their activation modes.A brief summary on the achievements and the challenges remaining in Nheterocyclic carbene(NHC)-catalyzed arene construction processes is provided at the end of this *** outlook into the future research direction within this field is also given based on our own opinion and knowledge on the trends of the development of NHC organocatalysis.

关键词： N-heterocyclic carbene arene construction cycloaddition organocatalysis

Piperazine:Its role in the discovery of pesticides

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中国化学快报:英文版 2023年第8期34卷 69-75页

作者： Wei Zhang Shengxin Guo Lijiao Yu Ya Wang yonggui robin chi Jian Wu National Key Laboratory of Green Pesticide Key Laboratory of Green Pesticide and Agricultural BioengineeringMinistry of EducationGuizhou UniversityGuiyang 550025China Division of Chemistry&Biological Chemistry School of Physical&Mathematical SciencesNanyang Technological UniversitySingapore 637371Singapore

Derivatives of piperazine,which is one of the most important heterocycles,are often used as linkers to connect active substructures that show promising bioactivities,especially in the field of *** 2000 to 2022,many piperazine-containing compounds were found to exhibit excellent activities against fungi,bacteria,insects,plant viruses,and weeds and have also been used as plant growth ***,the development of novel pesticides to prevent the invasion of crop pathogens and ensure the quality and yields of crops is still *** herein investigated and summarized the role that piperazine plays in the discovery of pesticides to provide a comprehensive summary of the broad activities of piperazine derivatives in agricultural applications and offer a potential reference for novel pesticide design using piperazine-containing ***,structure–activity relationships(SARs)analyses of bioactive piperazine-containing compounds are also discussed for a deeper understanding.

关键词： Piperazine Innovation of pesticides Activity Research review Structure-activity relationship

N-Heterocyclic carbene catalyzed C-acylation reaction for access to linear aminoenones

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chinese Chemical Letters 2023年第1期34卷 357-361页

作者： Jie Lv Yingling Nong Kai Chen Qingyun Wang Jiamiao Jin Tingting Li Zhichao Jin yonggui robin chi State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering Key Laboratory of Green Pesticide and Agricultural Bioengineering Ministry of EducationGuizhou UniversityGuiyang 550025China

An N-heterocyclic carbene(NHC)-catalyzed carbonyl nucleophilic substitution reaction between 1-cyclopropylcarbaldehydes and N-sulfonyl imines is developed for access to linearβ-aminoenone ***β-aminoenones containing cyclopropyl fragments can be afforded in moderate to excellent yields under mild *** reaction features excellent trans-diastereoselectivities and the desired aminoenone products are all afforded as Z-isomers.

关键词： N-Heterocyclic carbene Organocatalysis C-Acylation reaction Animoenone synthesis

Construction of Multi-Substituted Benzenes via NHC-Catalyzed Reactions of Carboxylic Esters

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chinese Journal of Chemistry 2018年第4期36卷 333-337页

作者： Jichang Wu Chengli Mou yonggui robin chi Laboratory Breeding Base of Green Pesticide and Agricultural Bioengi- neering Key Laboratory of Green Pesticide and Agricultural Bioengi- neering Ministry of Education Guizhou University Huaxi District Gui- yang Guizhou 550025 China School of Pharmacy Guiyang College of Traditional Chinese Medicine Huaxi District Guiyang Guizhou 550025 China

A carbene-catalyzed ester activation reaction for the synthesis of multi-substituted benzenes is developed. Tetra-substituted benzene com- pounds are efficiently synthesized through this methodology. Compared with aldehyde substrates used in previous reports, the ester substrates used here are much more readily available and inexpensive. In addition, the TEMPO oxidant used here is more inexpensive than the quinones commonly used in related carbene-catalyzed reactions.

关键词： N-heterocyclic carbene carboxylic ester benzene synthesis organocatalysis TEMPO oxidation

N-Heterocyclic Carbene Organocatalysis: Activation Modes and Typical Reactive Intermediates

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chinese Journal of Chemistry 2020年第10期38卷 1167-1202页

作者： Xingkuan Chen Hongling Wang Zhichao Jin yonggui robin chi Department of Chemistry Jinan UniversityGuangzhouGuangdong 510632China Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering Key Laboratory of Green Pesticide and Agricultural BioengineeringMinisry of EducationGuizhou UniversityHuaxi DistrictGuiyangGuizhou 550025China Division of Chemistry&Biological Chemistr School of Physical&Mathematical SciencesNanyang Technological UniversitySingopore 637371Singapore

N-Heterocyclic carbene(NHC)organocatalysis has been developed as an important approach in modern organic *** activation modes within NHC organocatalysis have been established with countless transformations being realized in both efficient and selective *** would like to provide an overview on the key progresses achieved within this field in the past two *** numerous excellent reviews have been documented within this area,we will mainly focus on the scientific development of this research field based on the basic reaction modes and typical reaction intermediates.

关键词： synthesis. catalysis Heterocyclic

Carbene-catalyzed activation of cyclopropylcarbaldehydes for mannich reaction andδ-lactam formation:remote enantioselecitvity control and dynamic kinetic asymmetric transformation

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Science china Chemistry 2021年第6期64卷 985-990页

作者： Jie Lv Jun Xu Xuling Pan Zhichao Jin yonggui robin chi State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering Key Laboratory of Green Pesticide and Agricultural BioengineeringMinistry of EducationGuizhou UniversityGuiyang 550025China School of Pharmacy Guizhou University of Traditional Chinese MedicineGuiyang 550025China Division of Chemistry&Biological Chemistry School of Physical&Mathematical SciencesNanyang Technological UniversitySingapore 637371Singapore

An N-heterocyclic carbene(NHC)-catalyzed enantioselective Mannich reaction of the remoteγ-carbon of cyclopropylcarbaldehydes is disclosed for the first ***-and enantiomerically enriched multicyclicδ-lactam compound is afforded as the main product from 8 possible stereo-specific isomers through dynamic kinetic asymmetric transformation(DYKAT)*** chiral functional molecules can be afforded from the lactam products through simple protocols with retentions of the optical purities.

关键词： N-heterocyclic carbene organocatalysis dynamic kinetic asymmetric transformation 1-cyclopropylcarbaldehydes asymmetric reactions

Desymmetrization of Cyclic 1,3-Diketones under N-Heterocyclic Carbene Organocatalysis:Access to Organofluorines with Multiple Stereogenic Centers

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Research 2021年第1期2021卷 1495-1507页

作者： Guanjie Wang Min Zhang Yezhi Guan Ye Zhang Xianfang Hong Chenlong Wei Pengcheng Zheng Donghui Wei Zhenqian Fu yonggui robin chi Wei Huang Key Laboratory of Flexible Electronics(KLOFE)&Institute of Advanced Materials(IAM)Nanjing Tech University(NanjingTech) 30 South Puzhu RoadNanjing 211816China College of Chemistry and Green Catalysis Center Zhengzhou UniversityZhengzhouHenan 450001China School of Chemistry and Molecular Engineering Nanjing Tech University(NanjingTech)30 South Puzhu RoadNanjing 211816China Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering Key Laboratory of Green Pesticide and Agricultural BioengineeringMinistry of EducationGuizhou UniversityHuaxi DistrictGuiyang 550025China Division of Chemistry&Biological Chemistry School of Physical&Mathematical SciencesNanyang Technological UniversitySingaporeSingapore 637371 Frontiers Science Center for Flexible Electronics(FSCFE)&Shaanxi Institute of Flexible Electronics(SIFE) Northwestern Polytechnical University(NPU)127 West Youyi RoadXi’an 710072China

Symmetric 1,3-diketones with fluorine or fluorinated substituents on the prochiral carbon remain to be ***,we have developed a novel prochiral fluorinated oxindanyl 1,3-diketone and successfully applied these substrates in carbene-catalyzed asymmetric ***,a versatile strategy for asymmetric generation of organofluorines with fluorine or fluorinated methyl groups has been *** stereogenic centers were selectively constructed with satisfactory *** diverse enantioenriched organofluorines were generated with excellent results in terms of yields,diastereoselectivities,and ***,exchanging fluorinated methyl groups to fluorine for this prochiral 1,3-diketones leads to switchable *** aspects and origin of stereoselectivity were studied by DFT ***,some of the prepared organofluorines demonstrated competitive antibacterial activities.

关键词： fluorine chiral asymmetric