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Chinese Journal of Chemistry 2015年第10期33卷 1124-1134页

作者： Baolei Wang Yanxia Shi Yizhou Zhan Liyuan Zhang Yan Zhang Lizhong Wang Xiao Zhang Yonghong Li Zhengming Li Baoju Li State-Key Laboratory of Elemento-Organic Chemistry Collaborative Innovation Center of Chemical Science and Engineering Nankai University Tianjin 300071 China Institute of Vegetables and Flowers Chinese Academy of Agricultural Sciences Beijing 100081 China

A series of novel furan/thiophene and piperazine-containing 1,2,4-triazole Mannich bases and bis（1,2,4-triazole） Mannich bases have been conveniently synthesized via Mannich reaction with triazole Schiff bases, various pipera- zinc derivatives, and formaldehyde as intermediates in good yields. Their structures were characterized by melting points, ~H NMR, 13C NMR, IR and elemental analysis. The preliminary bioassay showed that most compounds ex- hibited significant in vitro and in vivo fungicidal activity against several test plant fungi. Among 32 new compounds, the trifluoromethyl-containing compounds showed superior activity than the methyl-containing ones. Several com- pounds, such as FS, F9, F10, G5, HT, 118, 13 and 14, were comparable with some commercial fungicides against different fungi during the present study and could be further structurally optimized. Meanwhile, several compounds showed good herbicidal activity against Brassica campestris at 100 ~tg/mL and KARl inhibitory activity at 200 μg/mL. However, compounds exhibited poor insecticidal activity against oriental armyworm at 200 μg/mL in the preliminary studies. The research results will provide useful information for the design and discovery of new agro- chemicals with novel heterocyclic structures.

关键词： 1,2,4-triazole Mannich base piperazine derivative biological activity

A Zinc TTR Complex with a Novel 2-D Structure (TTR=3-Amino-1H-1,2,4-triazole)

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Chinese Journal of Structural Chemistry 2007年第6期26卷 703-706页

作者：周薇薇刘冰陈文通郑发鲲陈久桐郭国聪黄锦顺 State Key Laboratory of Structural Chemistry Fujian Institute of Research on the Structure of Matter The Chinese Academy of Sciences Graduate School of the Chinese Academy of Sciences Beijing 100039 China

The solvothermal reaction of 3-amino-1H-1,2,4-triazole （ttr） with Zn（ClO4）2·6H2O and NaCl in a 1：1：1 molar ratio gave a new complex [Zn（ttr）Cl]n with a 3-connected （4.82） 2-D structure. The layers stack in the -ABAB- way along the c axis with abundant hydrogen bonding interactions to form the crystal structure. The complex [Zn（ttr）Cl]n crystallizes in the orthorhombic space group Pbca with a = 9.369（1）, b = 10.049（1）, c = 11.905（1）A, V = 1120.9（3）A^3, Z = 8.00, C2N4H3ZnCl, Mr = 183.90, Dc = 2.180 g/cm^3,μ = 4.740 mm^-1, F（000） = 720, S = 1.059 and T = 293（2） K. The final R = 0.0662 and wR = 0.2457 for 956 observed reflections with Ⅰ〉 2σ（Ⅰ）, and R = 0.0689 and wR = 0.2504 for all data.

关键词： 1,2,4-triazole zinc（Ⅱ） 2-D network （4.82） net crystal structure

Synthesis,Crystal Structure and Biological Activity of a Novel Complex:Co(L)_2(CH_3OH)_2Cl_2 (L=3-(1,2,4-triazole-yl)-6-chloro-pyridazine)

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Chinese Journal of Structural Chemistry 2008年第3期27卷 357-361页

作者：汤宇李秀荣韩新利张智慧 Institute of Chemistry Nankai University

The title compound, Co（L）2（CH3OH）2Cl2 （L = 3-（1,2,4-triazole-yl）-6-chloro-pyridazine） 1, has been synthesized and its crystal structure has been determined by X-ray analysis. Complex 1 crystallizes in the triclinic system, space group P1 with a = 6.018（3）, b = 9.832（5）, c = 9.921（5）A, a = 78.270（8）, β = 74.550（8）, γ = 83.807（8）°, V = 553.1（5）A^3, Z = 1, C14H16Cl4CoN10O2, Mr = 557.10, Dc = 1.673 g/cm^3, F（000） = 281,μ（MoKα） = 1.293 mm^-1, the final R = 0.0453 and wR = 0.1181 for 1539 observed reflections with I 〉 2σ（I）. The Co（II） ion is in a distorted centrosymmetric six-coordinate octahedral environment with two Ntriazole, two Omethanol and two Cl atoms. Via hydrogen bonds the configuration of 1 has been extended into 1D chains which are developed to 2D layers via π-π sticking action, and these layers are further extended into a 3D network by hydrogen bonds. The antibacterial activity of the title compound has been detected, and the results show that the ligands and cobalt（II） complex exhibit certain fungicidal activity against several bacteria. Furthermore, the spectral properties of the title compound have been also studied and discussed.

关键词： 1,2,4-triazole pyridazine cobalt（II） complex crystal structure 1D chain

Synthesis and Crystal Structure of 5-[(1H-1,2,4-Triazol-1- yl)methyl]-4-(2,3-dimethoxybenzylideneamino)-2-2H-1,2,4-triazole-3(4H)-thione Monohydrate

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Chinese Journal of Structural Chemistry 2006年第6期25卷 673-676页

作者： XU Liang-Zhong SHANG Yu-Qing YU Guan-Ping LI Kai SI Guo-Dong College of Chemistry and Molecular Engineering Qingdao University of Science and Technology Qingdao 266042 China

The title compound 5-[（1H-1,2,4-triazol-1-yl）methyl]-4-（2,3-dimethoxy-benzylideneamino）- 2H-1,2,4-triazole-3（4H）-thione monohydrate 4 has been synthesized by the treatment of 4-amino-3-（ 1,2,4-triazol- 1-yl）- 1 H- 1,2,4-triazole-5（4H）-thione 3 with 2,3-dimethoxybenzaldehyde. It crystallizes as a monohydrate in the triclinic system, space group P1^- with a = 8.147（2）, b = 10.820（2）, c = 10.835（2）A, α= 73.770（6）, β = 84.916（7）,γ = 70.679（6）°, C14H17N7O35, Mr = 363.41, V= 865.4（2）A^3, Z= 2, Dc = 1.395 g/cm^3, F（000） = 380, μ = 0.217 mm^-1, the final R = 0.0400 and wR = 0.0975 for 3454 unique reflections. The dihedral angles made by the thione-substituted triazole ring with the other triazole ring and benzene ring are 74.92（3） and 14.81（2）°, respectively. There are some weak hydrogen bonds and C-H..π supramolecular interactions in the lattice, forming a three-dimensional network, which stabilizes the crystal structure.

关键词： 1,2,4-triazole crystal structure synthesis

Design, Synthesis and Biological Activities of Novel 4,5-Disubstituted-3-S-（β-D-acetylglycosyl）- 1,2,4-triazole Derivatives

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Chemical Research in Chinese Universities 2017年第5期33卷 758-764页

作者： CHENG Dandan WEI Wei LI Yuxin HUA Xuewen ZHOU Yunyun LIU Jingbo LI Yonghong YU Shujing XIONG Lixia LI Zhengming State Key Laboratory of Elemento-Organic Chemistry Institute of Elemento-Organic Chemistry Collaborative Innovation Center of Chemical Science and Engineering(Tianjin)College of Chemistry Nankai University Tianjin 300071 P. R. China College of Agriculture Liaocheng University Liaocheng 252000 P. R. China State Key Laboratory of Molecular Engineering of Polymers Department of Macromolecular Science Fudan University Shanghai 200433 P. R. China

A series of novel 4,5-disubstituted-3-S-（β-D-acetylglycosyl）-l,2,4-triazole derivatives was designed and synthesized via the strategy of introducing S-β-D-acetylglycosyl fragments into 1,2,4-triazole ring. The structures of 17 target compounds were characterized by means of lH NMR, 13C NMR and high-resolution mass spectrometer （HRMS）. The results of insecticidal activity indicated that compound 5a displayed 60% lethality rate at 100 mg/L concentration. More importantly, the introduction of the carbohydrate fragment to the 1,2,4-triazole core could im- prove the insecticidal activities since the insecticidal activities of compounds 5 were better than those of compounds 4 and this result was also supported by calcium imaging technique. The antifungal activity of the target compounds showed that some novel compounds displayed moderate to good inhibition rate against Sclerotinia sclerotiorum and Botrytis cinerea, in which compound 5p exhibited 78.8% inhibition rate against Sclerotinia sclerotiorum and 68.6% inhibition rate against Botrytis cinerea. The herbicidal activities of compounds 5 against Brassica campestris indi- cated that most of the target compounds showed moderate to good activities, especially compound 5g which showed 52.9% herbicidal activity at the concentration of 200 mg/L.

关键词： 1,2,4-triazole S-β-D-acetylglycosyl Biological activity

Synthesis and Biological Evaluation of 3,3-Dimethyl-1-(1H-1,2,4-triazole-1-yl)butan-2-One Derivatives as Plant Growth Regulators

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Chemical Research in Chinese Universities 2019年第2期35卷 221-228页

作者： CAI Guangrong ZUO Guanqiang ZHENG Dianfeng FENG Naijie College of Agronomy Heilongjiang Bayi Agricultural UniversityDaqing 163000P.R.China College of Agronomy Guangdong Ocean UniversitiyZhanjiang 524088P.R.China

We synthesized nine novel triazole-compoimds and investigated their plant growth regulatory activity.Compoimd CGR3,with metlioxvacyl on 3-position of triazole ring,showed better activity,promoting root length not only for mungbean,but also tor wheat.Additionally,CGR3 changed the level of endogenous hormones in mungbean roots,the most obvious effect was the increase of IAA,being 4.9 times greater than that of the control at the 96th hour after treatment.Among the synthesized new 1,2,4-triazol derivatives,CGR3 could be applied as a new agrochemical,functioning as a root growth stimulant,which promotes primary root length,influences the levels of endogenous honnones(IAA,ABA and GA3)to play an important role in controlling the primary root development.

关键词： 1,2,4-triazole derivatives Plant growth regulatary activity Roots

Synthesis,Crystal Structure and Biological Activities of 1-((5-(4-(4-Chlorophenoxy)-2-chlorophenyl)-2,2,3-trimethyloxazolidin-5-yl)methyl)-1H-1,2,4-triazole

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Chinese Journal of Structural Chemistry 2008年第11期27卷 1365-1369页

作者：许良忠毕文照杨志孟凡磊朱琪 College of Chemistry and Molecular Engineering Qingdao University of Science and Technology

The title compound 1-（（5-（4-（4-chlorophenoxy）-2-chlorophenyl）-2,2,3-trimethyl-oxazolidin- 5-yl）methyl）-lH-1,2,4-triazole （C21H22Cl2N4O2）has been synthesized and characterized by elemental analysis, IR, 1H NMR, MS and single-crystal X-ray diffraction. The crystal belongs to the triclinic system, space group Pi with a = 6.891（2）, b = 9.074（2）, c = 18.258（4）AA, α = 99.292（4）, β = 95.105（4）, γ = 108.068（3）°, C21H22Cl2N4O2, Mr = 433.33, V= 1059.3（4） Aa, Z = 2, Dc = 1.359 g/cm3, F（000） = 452,μ = 0.331 mm-1, the final R = 0.0448 and wR = 0.0994 for 3727 unique reflections. The dihedral angle between the oxazolidine ring taking an envelope conformation with a local pseudo-mirror and the triazole ring is 27.7（9）°. Weak intermolecular C-H...N hydrogen bonds and π-π interactions exist between the triazole rings of neighboring molecules, forming a three-dimensional network, which stabilizes the crystal structure. The primary biological test shows the target compound has certain fungicidal activity.

关键词： 1,2,4-triazole crystal structure synthesis fungicidal activity

Crystal Structure and Spectral Characters of 2-(4-Methylbenzoly)-3-(4-chlrolphenyl) -4-(1,2,4-triazole)-5-anilino-thiopene

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Chinese Journal of Structural Chemistry 2004年第7期23卷 739-742页

作者：许良忠建方方曹克广王忠卫 New Materials & Function Coordination Chemistry Laboratory Qingdao University of Science and TechnologyQingdao 266042China School of Chemical Industry and Material Beijing Institute of TechnologyBeijing 100081ChinaChengde Petroleum CollegeChengde 067000China School of Chemical Industry and Material Beijing Institute of TechnologyBeijing 100081China

The title compound 2-(4-methylbenzoly)-3-(4-chlrolphenyl)-4-(1,2,4-triazole)-5- anilino-thiopene has been prepared and characterized by IR, EA, 1H NMR, UV, MS and X-ray analysis. It crystallizes in the triclinic system, space group P1 with a = 8.061(2), b = 9.981(2), c = 15.462(3) ? a = 90.96(3), b = 103.11(3), g = 106.26(3)? Mr = 470.96 (C26H19ClN4OS), V = 1158.8(4) 3, Z = 2, Dc = 1.350 g/cm3, F(000) = 488, = 0.282 mm-1, R = 0.0482 and wR = 0.1043. In the crystal lattice, there exist some intermolecular hydrogen bonds, - stacking interactions and CH贩?supramolecular interactions. In the solid state, all of the above intermolecular interactions in the title compound can stabilize the crystal structure.

关键词： crystal structure thiopene 1,2,4-triazole hydrogen bond

Efficient synthesis and in vitro antifungal activity of 1H-benzimidazol-l-yl acetates/propionates containing 1H-1,2,4-triazole moiety

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Chinese Chemical Letters 2012年第12期23卷 1381-1384页

作者： Pei Zhi Zhang Shao Fang Zhou Tian Ren Li Lin Jiang College of Chemistry and Material Science Shandong Agricultural University

A series of novel 1H-benzimidazol-1-yl acetates and 1H-benzimidazol-1-yl propionates containing 1H-1,2,4-triazole moiety were synthesized under microwave irradiation by multi-step reactions, in yields of 87-94%. Their in vitro antifungal activities against Botrytis cinerea and Sclerotinia sclerotiorum were evaluated by mycelial growth rate method. All the target compounds exhibit high activities against B. cinerea with the EC50 values of 7.96-21.74 μg/mL, higher than that of carbendazim.

关键词： Benzoimidazole 1,2,4-triazole Synthesis Antifungal 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