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Chinese Journal of Chemistry 2011年第2期29卷 288-296页

作者： Wang Shouxin Wang Huan Fan Zhijin Fu Yifeng Mi Na Zhang Jufang Zhang Zhengcai Belskaya Nataliya P. Bakulev Vasiliy A. School of Pharmaceutical Science and Technology Tianjin University Tianjin 300072 China State Key Laboratory of Elemento Organic Chemistry Nankai University Tianjin 300071 China The Ural Federal University NamedAfier the First President of Russia B. N. Yeltsin Yeltsin UrFU 620002 Ekaterinburg Russia

A series of novel 3,5-dichloro-4-（1,1,2,2-tetrafluoroethoxy）phenyl containing 4-methyl-l,2,3-thiadiazole derivatives were designed and synthesized via Ugi reaction. Their structures were confirmed by IR, 1H NMR, 13C NMR and high-resolution mass spectroscopy. The preliminary bioassay results indicated that some title compounds had good fungicide activity at 50 ug/mL; most of the compounds presented a certain degree of direct inhibition activity, good inactivation and curative activity against tobacco mosaic virus at 500 ug/mL and 100 ug/mL; some compounds showed good larvicidal activity against Plutella xylostella L. at 200 ug/mL and excellent larvicidal activities against Culex pipiens pallens at 2 ug/mL.

关键词： 1,2,3-thiadiazole Ugi reaction synthesis design biological activity multicomponent reactions

Synthesis, X-ray Structure and Bioactivity of N-4-Methyl-1,2,3-thiadiazole-5-carbonyl-N′-3,5- dichloro-4-(1,1,2,2-tetrafluoroethoxyl)phenyl Urea

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Chinese Journal of Structural Chemistry 2012年第12期31卷 1721-1728页

作者：国丹丹王盾范志金李娟娟宋海斌范谦 Tatiana A. Kalinina Morzherin Yury Yur'evich Belskaya N. Pavlovna Bakulev V. Alekseevich State Key Laboratory of Elemento Organic Chemistry Nankai University Sichuan Functional Heterocyclic Compounds Engineering Technology Research Center The Ural Federal University Named after the First President of Russia B. N. Yeltsin

The title compound N-4-methyl-1,2,3-thiadiazole-5-carbonyl-N＇-3,5-dichloro-4- （1,1,2,2- tetrafluoroethoxyl）phenyl urea （C13H8Cl2F4N4O3S, Mr = 447.19） has been synthesized from 4-methyl- 1,2,3-thiadiazole-5-carbonyl chloride as the starting material, and its structure was characterized by proton Nuclear Magnetic Resonance （1H NMR）, Infra Red Spectroscopy （IR）, high-resolution mass spectroscopy （HRMS）, and single-crystal X-ray diffraction. The crystal of the title compound belongs to triclinic, space group Pi with a = 6.0780（8）, b = 11.3760（14）, c = 12.1440（18） A, α = 96.887（7）, β = 91.027（12）, γ= 104.252（13）°, Z = 2, V= 806.98（19）A3, Dc = 1.840 g/cm3, μ= 0.601 mm-1, F（000） = 448, R = 0.0450 and wR = 0.0869. X-ray analysis indicates that the 1,2,3-thiadiazole ring is not coplanar with the phenyl ring, and the dihedral angle is 33.57°. Two intermolecular hydrogen bonds N（2）-H…O（1 ）, S（1 ）…H-C（11）, and three weak intermolecular interactions, C（11）…O（1）, N（1）…O（2） and S…O（1）, are observed. The bioassay results indicate that the title compound has good insecticidal activity against Culex pipiens pallens and good induction activity for tobacco against tobacco mosaic virus which is equal to that of TDL.

关键词： crystal structure 1,2,3-thiadiazole synthesis biological activity

Synthesis and Biological Activities of Novel 1,2,4-Triazole Derivatives Containing 1,2,3-thiadiazole Ring

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Chemical Research in Chinese Universities 2014年第3期30卷 390-395页

作者： LI Yuedong MAO Wutao FAN Zhijin LI Juanjuan FANG Zhen JI Xiaotian ZONG Guangning LI Fengyun State Key Laboratory of Elemento-organic Chemistry Nankai University Tianjin 300071 P. R. China College of Chemistry and Pharmacy Engineering Nanyang Normal University Nanyang 473061 P R. China Collaborative Innovation Center of Chemical Science and Engineering(Tianjin) Nankai University Tianjin 300071 P. R. China

A series of novel 1,2,4-triazole derivatives containing 1,2,3-thiadiazole ring was designed and synthesized. Their structures were confirmed by IR, 1^H NMR, high resolution mass spectrometer（HRMS） and electrospray ionization-mass spectromcter（ESI-MS） combined with melting points and elemental analysis. Preliminary bioassays indi- cate that these compounds exhibit good insecticidal activity against Aphis laburni at 100 μg/mL, especially compound 6b shows mortality of no less than 95%. Most of the compounds show good activities against tobacco mosaic virus（TMV） with different modes in vivo at 100 μg/mL. Compound 6d standed out, showing a good insecticidal activity and very high induction effects against TMV in vivo. Collectively, our data demonstrate a new strategy for insect and virus control.

关键词： 1,2,3-thiadiazole 1,2,4-Triazole Insecticidal activity Anti-tobacco mosaic virus(TMV) activity

Synthesis and bioactivity of N-tert-butyl-N′-acyl-5-methy 1-1,2,3-thiadiazole-4-carbohydrazides

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Chinese Chemical Letters 2012年第11期23卷 1233-1236页

作者： Wu Tao Mao Hui Zhao Zhi Jin Fan Xiao Tian Ji Xue Wen Hua Tatiana Kalinina Yu.Morzherin Yury A.Bakulev Vasiliy Department of Chemistry Tianjin UniversityTianjin 300072China State Key Laboratory of Elemento-Organic Chemistry Nankai UniversityTianfin 300071China The Ural Federal University Named after the First President of Russia B.N.Yeltsin Yeltsin UrFU 620002EkaterinburgRussia

A series of novel N-tert-butyl-N＇-acyl-5-methyl-1,2,3-thiadiazole-4-carbohydrazides were designed and synthesized. Their structures were characterized by melting points, ^1H NMR, IR, ESI-MS, and elemental analysis. The bioassay tests indicated that compound 7o exhibited excellent direct anti-TMV activity and induction activity in vivo at 50μg/mL, which was better than that of Ninamycin and tiadinial. Our studies indicated that 1,2,3-thiadiazole was an active substructure for novel pesticide development.

关键词： Antivirus activity Systemic acquired resistance Synthesis 1,2,3-thiadiazole Diacylhydrazine

Synthesis,Crystal Structure and Biological Activity of N-cyanosulfoximine Derivative Containing 1,2,3-thiadiazole

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Chinese Journal of Structural Chemistry 2015年第9期34卷 1428-1433页

作者：毛武涛宗广宁范志金李凤云宋海斌李娟娟 Kalinina A.Tatiana Khazhieva Inna Lugovik Ksenia Morzherin Yu.Yury Belskaya P.Nataliya State Key Laboratory of Elemento-Organic Chemistry Collaborative Innovation Center of Chemical Science and Engineering (Tianjin)Nankai University College of Chemistry and Pharmacy Engineering Nanyang Normal University The Ural Federal University Named after the First President of Russia B.N.Yeltsin

The title compound N-cyanosulfoximine derivative containing 1,2,3-thiadiazole （C6HsN4OS2, Mr = 216.28） has been synthesized using 4-（chloromethyl）-5-methyl-1,2,3-thiadiazole as the starting material, and its structure was characterized by IR, 1H NMR, HRMS, elemental analysis and single-crystal X-ray diffraction. The crystal of the title compound belongs to orthorhombic, space group Pna21 with a = 14.730（6）, b = 5.478（2）, c = 22.619（9） A, Z = 8, V = 1825.0（13） A3, Dc = 1.574 g/cm3,/a = 0.547 mm-1, F（000） = 896, R = 0.0767 and wR （I〉 2o（/）） = 0.2064. X-ray analysis indicates that in this crystal double enantiomers are found as the basically asymmetrical unit and interactions between S（1）...N（3）, S（3）...N（4） and S（3）...N（7） are observed. This kind of interactions extends the molecules into a one-dimensional double chain. The preliminary biological test showed that the title compound had insecticidal activity against Myzus persicae in a certain degree and also presented moderate potential bioactivity against tobacco mosaic virus （TMV）.

关键词： 1,2,3-thiadiazole sulfoximine crystal structure synthesis biological activity

Synthesis, Crystal Structure and Biological Activity of N-(tert-butyl)-N'-(2-(4-chlorophenyl)acetyl)-5-methyl-1,2,3-thiadiazole-4-carbohydrazide

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Chinese Journal of Structural Chemistry 2013年第5期32卷 673-678页

作者：王盾毛武涛范志金李娟娟黄云宋海斌范谦 Tatiana A. Kalinina Glukhareva Tatiana Morzherin Yury Yur'evich Belskaya N. Pavlovna Bakulev V. Alekseevich Department of Plant Pathology Sichuan Agricultural University State Key Laboratory of Elemento-organic Chemistry Nankai University Sichuan Functional Heterocyclic Compounds Engineering Technology Research Center Lier Chemicals Co.Ltd. The Ural Federal University Named after the First President of Russia B. N. Yeltsin

The title compound N-（tert-butyl）-N＇-（2-（4-chlorophenyl）acetyl）-5-methyl-1,2,3-thiadiazole-4-carbohydrazide （C16H19ClN4NaO2S, Mr = 366.86） has been synthesized, and its structure was characterized by IR, 1H NMR, H RMS and single-crystal X-ray diffraction. The crystal of the title compound belongs to triclinic, space group Pī with a = 8.464（2）, b = 10.192（2）, c = 11.757（2）, α = 68.48（3）, β = 76.31（3）, γ = 80.86（3）°, Z = 2, V = 2024.6（10） 3, Dc = 1.333 g/cm3, μ = 0.339 mm-1, F（000） = 384, R = 0.0450 and wR （Ⅰ 〉 2σ（Ⅰ）） = 0.1234. X-ray analysis indicates one N-H…N intermolecular hydrogen bond and no π-π stacking interactions are observed in this crystal structure. The preliminary biological test shows that the title compound has fungicidal activity and antivirus activities against tobacco mosaic virus.

关键词： X-ray diffraction crystal structure synthesis 1,2,3-thiadiazole biological activity

Synthesis,Crystal Structure and Biological Activity of N-tert-butyl-N-(4-methyl-1,2,3-thiadiazole)-5-yl-N’-(4-methyl-1,2,3-thiadiazole)-5-formyl-N’-3,5-dichloropyridin-2-yl-diacylhydrazine

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Chinese Journal of Structural Chemistry 2011年第3期30卷 412-416页

作者：王唤付一峰范志金宋海斌吴青君张友军 Belskaya N.P. Bakulev V.A. State Key Laboratory of Elemento Organic Chemistry Nankai University Institute of Vegetables and Flowers Chinese Academy of Agricultural Sciences The Ural Federal University Named after the First President of Russia B. N. Yeltsin

The title compound N-tert-butyl-N-（4-methyl-1,2,3-thiadiazole）-5-yl-N＇-（4-me-thyl-1,2,3-thiadiazole）-5-formyl-N＇-3,5-dichloropyrid-2-yl-diacylhydrazines （C18H17Cl2N7O3S2, Mr = 514.41） has been synthesized by the reaction of N-tert-butyl-N＇-3,6-dichloropyridine-2-formyl hydrazine with 4-methyl-1,2,3-thiadiazole-5-carbonyl chloride and triethylamine, and its structure was characterized by 1H NMR, HR MS, and single-crystal X-ray diffraction. The crystal of the title compound belongs to monoclinic, space group C2/c with a = 27.726（8）, b = 11.045（3）, c = 14.507（4）A, β = 96.758（4）°, Z = 8, V = 4412（2） A^3, Dc = 1.549 g/cm^3, μ = 0.521 mm^-1, F（000） = 2112, R = 0.0405 and wR = 0.1153. X-ray analysis indicates that all rings are non-planar in this molecule. The bioassay results indicate that both the title compound and the positive control RH-5992 have weak fungicide activities, while the title compound has good insecticidal activity against Plutella xylostella L. and no insecticidal activity against Culex pipiens pallens.

关键词： crystal structure 1,2,3-thiadiazole synthesis biological activity

Synthesis and Crystal Structure of 3,6-Bis(4-methyl-1,2,3-thiadiazol-5-yl)-1,2,4-triazolo[3,4-b][1,3,4]thiadiazole

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Chinese Journal of Structural Chemistry 2010年第1期29卷 13-16页

作者：杨知昆范志金左翔郑琴香宋海斌尤进茂 NATALIA P.Belskaia VASILIY A.Bakulev State Key Laboratory of Elemento Organic Chemistry Nankai University Department of Chemistry Qufu Normal University TOSLab The Urals State Technical University

The compound 3,6-bis（4-methyl-1,2,3-thiadiazol-5-yl）-1,2,4-triazolo[3,4-b][1,3,4] thiadiazole（C9H6N8S3,Mr = 322.40） has been synthesized by the reaction of 4-amino-3-（4-methyl-1,2,3-thiadiazolyl）-5-mercapto-1,2,4-triazole with 4-methyl-1,2,3-thiadiazol-5-carboxylic acid and phosphorus oxychloride,and its structure was characterized by IR,1H NMR,EI-MS,elemental analysis and single-crystal X-ray *** crystal of the title compound belongs to monoclinic,space group C2/c with a = 2.0053（4）,b = 1.3081（3）, c = 1.0556（2） nm, β = 112.69（3）°,Z = 4, V= 2.5548（9） nm^3, Dc = 1.676 g/cm^3, μ= 0.582 mm^-1, F（000） = 1312, R = 0.0546 and wR = 0.1523. X-ray analysis indicates that all rings are essentially planar in this molecule, and an intermolecular hydrogen bond C（9）-H（9）…N（2） and weak intramolecular interactions between S（1）…N（7）, S（3）…N（1） and S（2）…N（4） are observed.

关键词： X-ray diffraction crystal structure synthesis 1,2,3-thiadiazole

Synthesis, Crystal Structure and Biological Activity of 1,5-Bis(4-methoxyphenyl)-3-(4-methyl-1,2,3-thiadiazol-5-yl)pentane-1,5-dione

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Chinese Journal of Structural Chemistry 2013年第3期32卷 357-362页

作者：毛武涛国丹丹范志金谷希树宋海斌王盾范谦 Kalinina Tatiana Yury Yu.Morzherin Vasiliy A.Bakulev Department of Chemistry School of ScienceTianjin University State Key Laboratory of Elemento-organic Chemistry Nankai University Institute of Plant Protection Tianjing Academy of Agricultural Sciences Sichuan Functional Heterocyclic Compounds Engineering Technology Research Center Lier Chemicals Co.Ltd. The Ural Federal University Named after the First President of Russia B. N. Yeltsin

The title compound 1,5-bis（4-methoxyphenyl）-3-（4-methyl-1,2,3-thiadiazol-5-yl）-pentane-1,5-dione （C22H22N2O4S, Mr=410.49） has been synthesized by the reaction of 4-methyl-1,2,3-thiadiazole-5-carbaldehyde with 4-methoxyacetophenone, and its structure was characterized by IR, 1H NMR, H RMS, elemental analysis and single-crystal X-ray diffraction. The crystal of the title compound belongs to monoclinic, space group P21/c with a=11.159（3）, b=9.002（3）, c=20.192（6）, β=93.393（5）°, Z=4, V=2024.6（10） 3 , Dc=1.347 g/cm3 , μ=0.191 mm-1 , F（000）=864, R=0.0333 and wR （I〉2σ （I））=0.0840. In this molecule, the 1,2,3-thiadiazol ring is nearly vertical with both phenyl rings, and intermolecular weak hydrogen bonds of C-H…O and C-H…N types together with π-π stacking interactions and interactions between S（1）…N（2） are observed. The above three kinds of interactions extend the molecules into a two-dimensional layer framework. The preliminary biological test showed that the title compound had fungicidal activity.

关键词： X-ray diffraction crystal structure synthesis 1,2,3-thiadiazole fungicidal activity

Synthesis, Crystal Structure and Biological Activity of Diethyl 1,4-dihydro-2,6-dimethyl-4-(4-methyl-1,2,3-thiadi azol-5-yl)pyridine-3,5-dicarboxylate

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Chinese Journal of Structural Chemistry 2014年第4期33卷 535-543页

作者：李娟娟华学文范志金姬晓恬宗广宁李凤云黄云宋海滨刘超伦 Yury Yu. Morzherin Nataliya P. Belskaya Vasiliy A. Bakulev Department of Plant Pathology Sichuan Agricultural University State Key Laboratory of Elemento-organic Chemistry Nankai University Collaborative Innovation Center of Chemical Science and Engineering(Tianjin) The Ural Federal University Named after the First President of Russia B. N. Yeltsin Yeltsin UrFU 620002 Ekaterinburg Russia

The title compound diethyl 1,4-dihydro-2,6-dimethyl-4-（4-methyl-1,2,3-thiadiazol- 5-yl） pyridine-3,5-dicarboxylate （C16H21N3O4S, Mr = 351.42） was prepared by the Hantszch reaction with 4-methyl-1,2,3-thiadiazole-5-formaldehyde, ethyl acetoacetate and ammonium acetate in the presence of aluminum chloride in alcohol, and its structure was characterized by IR spectra, 1H-NMR, EA, and single-crystal X-ray diffraction. The crystal of the title compound belongs to monoclinic system, space group P21/n with α= 11.300（2）, b = 12.771（3）, c = 12.826（3）？, β = 96.55（3）o, V = 1839.0（6）？3, Z = 4, Dc = 1.296 g/cm3, μ（MoKa） = 0.71073 mm-1, F（000） = 744, R = 0.0981 and wR = 0.1994. X-ray diffraction result shows that the torsion angles of N（1）–C（2）– C（3）–C（4） and C（2）–C（3）–C（4）–C（8） are 178.9（3）° and –130.3（3）°, respectively. All rings in the title compound are non-planar. The bioassay results indicate that the title compound has good fungicidal activity, good antivirus activity against tobacco mosaic virus and certain extent of insecticidal activity against Mythimna separata.

关键词： 1,4-dihydropyridine 1,2,3-thiadiazole crystal structure biological activity