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Synthesis and insecticidal activity of Novel N-Pyridylpyrazole Carbonyl Thioureas

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Chinese Journal of Chemistry 2012年第4期30卷 815-821页

作者：王宝雷马翼熊丽霞李正名 State-Key Laboratory of Elemento-Organic Chemistry Institute of Elemento-Organic ChemistryNankai UniversityTianjin 300071China

A series of novel N-pyridylpyrazole carbonyl thioureas were designed and synthesized. Their structures were characterized by melting points, 1H NMR, IR and elemental analysis or HRMS. The bioassay tests indicated that some of these compounds exhibited moderate insecticidal activity against Mythirnna separata Walker and Culex pipiens pallens. Among 17 compounds, 5n and 5p showed 100% larvicidal activity against Mythimna separata Walker at the test concentration of 100 mg/L.

关键词： carbonyl thiourea insecticidal activity N-pyridylpyrazole

Synthesis,Crystal Structure and insecticidal activity of N-(pyridin-2-ylmethyl)-1-phenyl-1,4,5,6,7,8-hexahydrocyclohepta[c]pyrazole-3-carboxamide

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Chinese Journal of Structural Chemistry 2018年第4期37卷 551-556页

作者：邓希乐周小毛王赞永芮昌辉杨新玲 Hunan Agriculture Biotechnology Research Institute Hunan Academy of Agricultural Sciences Department of Applied Chemistry College of ScienceChina Agricultural University Laboratory of Integrated Pest Management in Crops Ministry of AgricultureInstitute of Plant ProtectionChinese Academy of Agricultural Sciences

The title compound N-（pyridin-2-ylmethyl）- 1-phenyl- 1,4,5,6,7,8-hexahydrocy-clohepta[c]pyrazole-3-carboxamide 5 （C21I-I22N40, Mr = 346.42） has been synthesized andstructurally characterized by IR, 1H NMR, 13C NMR, H RMS and single-crystal X-raydiffraction. The crystal crystallizes in monoclinic system, space group P21/n with a = 8.668（2）,b = 22.236（4）, c = 9.539（2） A, β = 108.68（3）°, V = 1786.4（7）/k3, Z = 4, Dx= 1.288 g/cm3,F（000） = 736,μ（MoKa） = 0.649 mm^-1, the final R = 0.0354 and wR = 0.0933 with 3234observed reflections with I 〉 2σ（/）. The benzene and pyrazole rings are nearly coplanar with adihedral angle of 50.977（46）°. The dihedral angle between the central pyrazole and pyridinerings is 11.688（46）°. No classical hydrogen bonds were found in the molecules. Two adjacentmolecules in crystal packing of compound 5 were linked by two intramolecularhydrogen-bonding interactions C（15）-H（15）…O（1） to generate a stable structure. Compound 5had weak insecticidal activity against the diamondback moth （Plutella xylostella）, butexhibited good activity against cotton bollworm （Helicoverpa armigera）.

关键词： synthesis bicyclic pyrazole amide crystal structure insecticidal activity

Synthesis,insecticidal activity and stability study of novel nitromethylene neonicotinoids with five-membered aromatic heterocycles

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Chinese Chemical Letters 2023年第6期34卷 391-394页

作者： Li Han Zihao Yuan Xusheng Shao Xiaoyong Xu Zhong Li Shanghai Key Laboratory of Chemical Biology School of PharmacyEast China University of Science and TechnologyShanghai 200237China Shanghai Collaborative Innovation Center for Biomanufacturing Technology Shanghai 200237China

Twenty-four novel neonicotinoid analogues with nitromethylene and five-membered aromatic heterocycles were designed and *** target molecular structures have been confirmed by analytical and spectral *** compounds exhibited notable insecticidal activities against aphid(Aphis medicaginis)and brown planthopper(Nilaparvata lugens).The aqueous stability test confirmed that the stabilities of those compounds were superior to the leading compound,and the photostability was even better than that of imidacloprid.

关键词： Nitromethylene Neonicotinoids Selective reduction Stability insecticidal activity

Synthesis, insecticidal activity and molecular docking study of clothianidin analogues with hydrazide group

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Chinese Chemical Letters 2014年第7期25卷 1017-1020页

作者： Shao-Hua Liu Wei Peng Yan-Yan Qu Dan Xu Hong-Yue Li Dun-Lun Song Hong-Xia Duan Xin-Ling Yang Department of Applied Chemistry College of ScienceChina Agricultural University Department of Entomology College of Agriculture and BiotechnologyChina Agricultural University

A series of novel neonicotinoid analogues were designed and synthesized by introducing a hydrazide group into clothianidin. Their structures were confirmed by IR, 1H NMR, and HRMS （ESI）. Preliminary bioassay showed that some compounds, Sb and Sg, exhibited good activity against soybean aphids （Aphis glycines） at 100 mg L ^-1. In addition, molecular docking with receptor was carried out to explain their different activity from clothianidin.

关键词： Clothianidin analogues Hydrazide group insecticidal activity Molecular docking

Design, Synthesis and insecticidal activity of Novel Anthranilic Diamides Containing Oxime Ester and Diacylhydrazine Moieties

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Chemical Research in Chinese Universities 2014年第2期30卷 228-234页

作者： LIU Chen ZHANG Jifeng ZHOU Yunyun WANG Baolei XIONG Lixia LI Zhengming State Key Laboratory of Elemento-Organic Chemistry Collaborative Innovation Center of Chemical Science and Engineering(Tianjin) Nankai University Tianjin 300071 P.R.China

Two series of novel anthranilic diamides containing oxime ester and diacylhydrazine moieties were designed and *** structures were characterized by melting points,1H NMR,13C NMR and high resolution mass spectrometry（HRMS）.The single crystal structure of compound 7e was determined by X-ray diffraction and their evaluated insecticidal activity against oriental armyworm（Mythimna separata） indicates that some of the compounds exhibited moderate insecticidal *** the 20 compounds,6a and 6b show 100％ larvicidal activity against Mythimna separate Walker at the test concentration of 100 mg/L.

关键词： Anthranilic diamide Oxime ester Diacylhydrazine insecticidal activity

Syntheses and insecticidal activity of Spirocyclic Tetronic Acid Derivatives Containing Oxime Ether Moiety

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Chemical Research in Chinese Universities 2020年第5期36卷 810-815页

作者： ZHAO Yang CHENG Jingli XIE Zhengang FANG Shaowei ZHAO Jinhao Ministty of Agriculture Key Laboratory of Molecular Biology of Crop Pathogens and Insert Institute of Pesticide and Environmental ToxicologyZhejiang UniversityHangzhou 310058P.R.China

In order to develop novel spirocyclic tetronic acid lead compounds,a series of new spirocyclic tetronic acid derivatives containing oxime ether moiety was synthesized and *** stmctures of 16 target compounds were characterized by lH NMR spectra,13C NMR spectra and high-resolution mass spectrometer(HRMS).Preliminary bioassays indicated that most of the title compounds displayed excellent insecticidal activity against Aphis fabae and Nilapmyata lugens at 100 mg/*** particular,compound 6k showed the similar activity(LC50=6.87 mg/L)against *** as the spirotetramat(LC50=4.56 mg/L)and had better efIects(LC50=l.64 mg/L)against *** in comparison with spirotetramat(LC5o=7.90 mg/L).The study showed that compound 6k exhibited more promising and broad-spectrum insecticide activity and may serve as a new insecticidal agent for sucking pests.

关键词： Spirocyclic tetronic acid derivative insecticidal activity Oxime ether moiety

Synthesis, Mechanism of Formation and insecticidal activity of Novel Fluorinated Organophosphorus Compounds

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Chinese Journal of Chemistry 2002年第12期20卷 1598-1601,1464页

作者：吴军 HUDSON Harry R. Department of Chemistry Zhejiang University Hangzhou Zhejiang 310027 China Division of Chemistry School of Biological and Applied Sciences University of North London London N7 8DB UK

The major products of the interaction between triethyl phosphite and 3-fluoropropanoyl chloride at room temperature are diethyl (E)-1-(3-fluoropropanoyloxy)-3-fluoroprop-1-enylphosphonate (3) and diethyl l-(diethoxyphosphoryl)-3-fluoropropyl phosphate (4). The compounds 3 and 4 were separated by chromatography, and structurally characterized by elemental analysis, NMR spectroscopy (1H, 13C, 19F and 31P) and mass spectrometry. Possible reaction mechanisms are proposed. The major products 3 and 4 were tested for insecticidal activity. 3 gave 100% control of Musca domestica L. and Phaedon cochledriae Fab. at a dose of 20 μg/per insect.

关键词： synthesis reaction mechanism insecticidal activity fluorinated organophosphonate

Design,synthesis,and insecticidal activity of novel terpenoid ester compounds containing bicyclo[2.2.1]heptane against Aphis gossypii Glover

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Advanced Agrochem

Advanced Agrochem 2024年第2期3卷 171-181页

作者： Caiyue Liu Yuelan Yin Hao Liu Longfei Yang Minghui Chen Ting Ma Guoqiang Zhang Chunjuan Wang Sifeng Zhao Xiaoqiang Han Key Laboratory of Oasis Agricultural Pest Management and Plant Protection Utilization College of AgricultureShihezi UniversityShiheziXinjiang832002China Department of Applied Chemistry China Agricultural UniversityBeijing100193China

To discover novel and efﬁcient compounds against Aphis gossypii Glover,a series of novel terpene ester derivatives containing the structure of bicyclo[2.2.1]heptane were designed and synthesized using tschimganin as the lead *** assays showed that most tschimganin analogs exhibited moderate to outstanding insecticidal activity against *** particular,compound 56(LC_(50)=0.28μg mL^(-1)),identiﬁed as(1S,2S,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl nicotinate,exhibited the best activity,which was signiﬁcantly superior to that of imidacloprid(LC_(50)=0.54μg mL^(-1))and sulfoxaﬂor(LC_(50)=0.70μg mL^(-1)).The precise and dependable 3D-QSAR model suggests a promising direction for further design of more active tschimganin-based *** showed that compound 56 disrupted detoxiﬁcation,amino acid biosynthesis,and energy metabolism and may affect the central nervous system of *** results of this study indicated that tschimganin analogs are a potential new class of green insecticides that can be used for the integrated management of ***.

关键词： Aphis gossypii Terpene ester insecticidal activity 3D-QSAR Metabolomics

insecticidal activity of Crystals and Spores of Purified Bacillus thuringiensis 00-50-5 Strain against Trichoplusia ni Hubner

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Plant Diseases and Pests 2013年第4期4卷 5-7页

作者： Liu Liping Cheng Bai Song Yingzi Chen Yipeng Peng Zhengqiang Key Laboratory of Pests Comprehensive Governance for Tropical Crops Ministry of AgricultureHainan Key Laboratory for Monitoring and Control of Tropical Agricultural PestsHainan Engineering Research Center for Biological Control of Tropical Crops Diseases and Insect PestsEnvironment and Plant Protection InstituteCATAS Experimental High School Attached to Bejing Normal University

[ Objective] The paper was to study pathogenic mechanism and action mode of Bacillus thuringiensis （Bt） 00-50-5 strain against Trichoplusia ni Hub- ner. [Method] The crystals and spores of B. thuringiensis 00-50-5 strain were first isolated and purified, and their insecticidal activities against T. ni were com- pared. [ Result] Either the mixture of pure crystals and pure spores of 00-50-5 strain, or only pure crystals could kill T. n/larvae under the concentration of 100 p.g/mL after 48 h, and the mortality rate reached 100% ; pure spores could not kill the larvae. Determination results of median lethal concentration showed that in- secticidal activity of pure crystal of Bt 00-50-5 strain （LGs0 =0.32 p~/mL） was higher than the mixture of crystals and spores （LCs0 =0.48）, but the insecticidal acti^ty of pure spores was very low （LC50 〉 500.00）. Therefore, the crystals were primarily responsible for causing death of larvae. [ Conclusion] The paper provides theoretical basis for application of Bt 00-50-5 strain.

关键词： Bacillus thuringiensis Pure crystal Pure spore Trichoplusia n/ insecticidal activity