Citation: Yu-Xing TAN, Yong-Lan FENG, Fu-Xing ZHANG, Jiang-Xi YU, Wu-Jiu JIANG, Dai-Zhi KUANG. Synthesis, crystal structure, and herbicidal activity of two tetranuclear di(n-butyl)tin aryloyacetates complexes with Sn4O8 cluster[J]. Chinese Journal of Inorganic Chemistry, ;2023, 39(4): 649-658. doi: 10.11862/CJIC.2023.031 shu

Synthesis, crystal structure, and herbicidal activity of two tetranuclear di(n-butyl)tin aryloyacetates complexes with Sn4O8 cluster

  • Corresponding author: Dai-Zhi KUANG, hnkcq@qq.com
  • Received Date: 23 September 2022
    Revised Date: 3 January 2023

Figures(6)

  • Two tetranuclear di(n‐butyl)tin aryloyacetates [(o‐R—C6H4—OCH2COOSn(n‐Bu)2)2O]2 (R=H (C1), Cl (C2)) have been synthesized by the reaction of phenoxyacetic acid or o‐chlorophenoxyacetic acid with dibutyltin oxide, respectively. The structures were characterized by elemental analysis, IR, 1H, 13C NMR, and X‐ray crystal diffraction. There is a ladder structure formed by a four‐membered central endocyclic Sn2O2 unit in the independent molecules of complexes C1 and C2, two carboxyl oxygen atoms and an Sn—O—Sn unit constituted the six‐membered ring on both sides of the ladder, which constitutes the Sn4O8 configuration. Thermogravimetric analysis shows that the complexes possess good thermal stability in the air atmosphere. Herbicidal activity results show that complex C1 has good regulative effects on the growth of Cassia tora Linn., and complex C2 has better inhibitory activity against the root and stalk of Amaranthus spinosus at the concentration of 50 mol·L-1.
  • 加载中
    1. [1]

      Kelly J A. Commercial herbicides, Present methods of formulation[J]. J. Agric. Food Chem., 1953,1(3):254-257. doi: 10.1021/jf60003a009

    2. [2]

      Żelechowski K, Zakrzewski J, Huras B, Kiełczewska A, Krawczyk M, Michalczyk A K, Hupko J, Jaszczuk K. Synthesis and herbicidal and fungistatic evaluation of Passerini adducts bearing phenoxyacetic moieties[J]. Chem. Pap., 2021,75(7):3047-3059. doi: 10.1007/s11696-021-01528-8

    3. [3]

      Huras B, Zakrzewski J, Kiełczewska A, Krawczyk M. Herbicidal and fungistatic properties of fluorine analogs of phenoxyacetic herbicides[J]. J. Fluorine Chem., 2017,202:76-81. doi: 10.1016/j.jfluchem.2017.08.013

    4. [4]

      Peterson D J, Ohio C. Novel organotin herbicidal compounds: US4055413. 1977-10-25.

    5. [5]

      Cheshire R J S, Woodbridge W L H, Jr R E G. Tetrasubstituted organotin compounds: US4260552. 1981-04-07.

    6. [6]

      CN931087090. 1995-01-25. XIE Q L, YANG Z Q, TAN S F, ZHOU X Z. Mixed trialkyl tin derivatives pesticide: CN931087090. 1995-01-25.

    7. [7]

      YANG Z Q, XIE Q L, ZHOU X Z. Studies on mixed trialkyltin derivatives-Ⅵ. The structure and bioactivities of methyldicyclohexyltin carboxylates[J]. Acta Chim. Sinica, 1995,53:721-728.  

    8. [8]

      CN201010615065.9. 2011-07-20. YIN H D, WEI X T, LI J. A diphenyl tin dichloride complex, The preparation method and application: CN201010615065.9. 2011-07-20.

    9. [9]

      Rehman A, Hussain M, Rehman Z, Ali S, Rauf A, Hassan Nasim F, Helliwell M. Self-assembled pentagonal bipyramidal and skew trapezoidal organotin (Ⅳ) complexes of substituted benzoic acids: Their antibacterial, antifungal, cytotoxic, insecticidal and urease inhibition activities[J]. Inorg. Chim. Acta, 2011,370:27-35. doi: 10.1016/j.ica.2011.01.007

    10. [10]

      Salam M A, Affan M A, Arafat M A, Saha R, Nasrin R. Synthesis, characterization, and antibacterial activities of organotin (Ⅳ) complexes with 2 acetylpyridineN (4) cyclohexylthiosemicarbazone (HAPCT)[J]. Heteroat. Chem., 2013,24(1):43-52. doi: 10.1002/hc.21061

    11. [11]

      Syed Annuar S N, Kamaludin N F, Awang N, Chan K M. Cellular basis of organotin (Ⅳ) derivatives as anticancer metallodrugs: A review[J]. Front. Chem., 2021,9657599. doi: 10.3389/fchem.2021.657599

    12. [12]

      Lagerström M, Strand J, Eklund B, Ytreberg E. Total tin and organotin speciation in historic layers of antifouling paint on leisure boat hulls[J]. Environ. Pollut., 2017,220:1333-1341. doi: 10.1016/j.envpol.2016.11.001

    13. [13]

      Rahman M M, Jusoh I, Affan M A, Husaini A, Hamdan S. Efficacy of novel organotin (Ⅳ) complexes on non-durable tropical wood against decay fungi[J]. Eur. J. Wood Prod., 2013,71:463-471. doi: 10.1007/s00107-013-0703-6

    14. [14]

      WANG C C, WANG P, LIU Y C, HE Y, WANG C Z. Determination of stannum content in dibutyltin dilaurate by atomic fluorescence spectrometric method[J]. Paint & Coatings Industry, 2011,41(9):70-72. doi: 10.3969/j.issn.0253-4312.2011.09.018

    15. [15]

      LIANG Y, SHI X P. Study on synthesis of phenoxyacetic acid[J]. Applied Chemical Industry, 2001,30(4):31-32. doi: 10.3969/j.issn.1671-3206.2001.04.012

    16. [16]

      WANG M Y, GUO W C, LAN F, LI Y H, LI Z M. Synthesis and herbicidal activity of N-(4'-substituted pyrimidin-2'-yl)-2-methoxycarbonyl-5[(un) substituted benzamido]phenylsulfonylurea derivatives[J]. Chinese J. Org. Chem., 2008,28(4):649-656.

    17. [17]

      Xu X L, Hu F, Ma Y W, Gao J M, Shuai Q. Facile microwave synthesis, structural diversity and herbicidal activity of six novel alkalineearth metal complexes (AECs) based on skeletal isomerization chlorophenoxyacetic acids[J]. New J. Chem., 2018,42(6):4155-4166. doi: 10.1039/C8NJ00107C

    18. [18]

      Zubair M, Sirajuddin M, Haider A, Hussain I, Tahir M N, Ali S. Organotin (Ⅳ) complexes as catalyst for biodiesel formation: Synthesis, structural elucidation and computational studies[J]. Appl. Organomet. Chem., 2020,34(1)e5305.

    19. [19]

      Adeyemi J O, Onwudiwe D C, Ekennia A C, Okafor S N, Hosten E C. Organotin (Ⅳ) N-butyl-N-phenyldithiocarbamate complexes: Synthesis, characterization, biological evaluation and molecular docking studies[J]. J. Mol. Struct., 2019,1192:15-26. doi: 10.1016/j.molstruc.2019.04.097

    20. [20]

      WENG S F. Fourier transform infrared spectroscopy. 2nd ed. Beijing: Chemical Industry Press, 2010: 305-306

    21. [21]

      Galván-Hidalgo J M, Roldán-Marchán D M, González-Hernández A, Ramírez-Apan T, Nieto-Camacho A, Hernández-Ortega S, Gómez E. Organotin (Ⅳ) complexes from Schiff bases ligands based on 2-amino-3-hydroxypyridine: Synthesis, characterization, and cytotoxicity[J]. Med. Chem. Res., 2020,29(12):2146-2156. doi: 10.1007/s00044-020-02630-4

    22. [22]

      BAO M, HE Q L, LIU B D, XING Y, LIN Y H. Synthesis and crystal structure of tris (2 methyl 2 phenyl propyl) tin (Ⅳ) phenoxyacetate[J]. Chinese J. Inorg. Chem., 1998,14(1):114-117.  

    23. [23]

      Jiang W J, Zhang Z J, Ni P H, Tan Y X. Self-assembly synthesis of diorganotin complexes based on arylformylhydrazone possessing ONO donor set: Anticancer activity and mechanism[J]. Metallomics, 2022,14(5)mfac021. doi: 10.1093/mtomcs/mfac021

    24. [24]

      JIANG W J, KUANG D Z, YU J X, FENG Y L, ZHANG F X, WANG J Q. Synthesis, crystal structure, quantum chemistry and thermal stability of the bis-oxygen-bridged tetranuclear dibutyltin (2, 4, 6-trimethyl) benzoate[J]. Chinese J. Inorg. Chem., 2012,28(11):23632368-2368.  

    25. [25]

      Li D M, Hu R T, Zhou W, Sun P P, Kan Y H, Tian Y P, Zhou H P, Wu J Y, Tao X T, Jiang M H. Synthesis, structures, and photophysical properties of two organostannoxanes from a novel acrylic acid derived from phenothiazine[J]. Eur. J. Inorg. Chem., 2009(18):2664-2672.

    26. [26]

      ZHENG G J, ZENG Z F, ZHANG H Q. Synthesis and herbicidal activity of N-aryloxyacetyl-N'-isonicotinamido thiourea[J]. Agrochemi-cals, 2020,59(10):715-718.

    27. [27]

      LIU K, ZHANG F, YANG H B, LI B. Study on herbicidal activity of piperidine imidazolindiones[J]. World Pesticide, 2022,44(3):40-46.  

  • 加载中
    1. [1]

      Xinting XIONGZhiqiang XIONGPanlei XIAOXuliang NIEXiuying SONGXiuguang YI . Synthesis, crystal structures, Hirshfeld surface analysis, and antifungal activity of two complexes Na(Ⅰ)/Cd(Ⅱ) assembled by 5-bromo-2-hydroxybenzoic acid ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1661-1670. doi: 10.11862/CJIC.20240145

    2. [2]

      Jingjing QINGFan HEZhihui LIUShuaipeng HOUYa LIUYifan JIANGMengting TANLifang HEFuxing ZHANGXiaoming ZHU . Synthesis, structure, and anticancer activity of two complexes of dimethylglyoxime organotin. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1301-1308. doi: 10.11862/CJIC.20240003

    3. [3]

      Haitang WANGYanni LINGXiaqing MAYuxin CHENRui ZHANGKeyi WANGYing ZHANGWenmin WANG . Construction, crystal structures, and biological activities of two Ln3 complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1474-1482. doi: 10.11862/CJIC.20240188

    4. [4]

      Xiaoling LUOPintian ZOUXiaoyan WANGZheng LIUXiangfei KONGQun TANGSheng WANG . Synthesis, crystal structures, and properties of lanthanide metal-organic frameworks based on 2, 5-dibromoterephthalic acid ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1143-1150. doi: 10.11862/CJIC.20230271

    5. [5]

      Xin MAYa SUNNa SUNQian KANGJiajia ZHANGRuitao ZHUXiaoli GAO . A Tb2 complex based on polydentate Schiff base: Crystal structure, fluorescence properties, and biological activity. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1347-1356. doi: 10.11862/CJIC.20230357

    6. [6]

      Yan Liu Yuexiang Zhu Luhua Lai . Introduction to Blended and Small-Class Teaching in Structural Chemistry: Exploring the Structure and Properties of Crystals. University Chemistry, 2024, 39(3): 1-4. doi: 10.3866/PKU.DXHX202306084

    7. [7]

      Weina Wang Fengyi Liu Wenliang Wang . “Extracting Commonality, Delving into Typicals, Deriving Individuality”: Constructing a Knowledge Graph of Crystal Structures. University Chemistry, 2024, 39(3): 36-42. doi: 10.3866/PKU.DXHX202308029

    8. [8]

      Junqiao Zhuo Xinchen Huang Qi Wang . Symbol Representation of the Packing-Filling Model of the Crystal Structure and Its Application. University Chemistry, 2024, 39(3): 70-77. doi: 10.3866/PKU.DXHX202311100

    9. [9]

      Jiaming Xu Yu Xiang Weisheng Lin Zhiwei Miao . Research Progress in the Synthesis of Cyclic Organic Compounds Using Bimetallic Relay Catalytic Strategies. University Chemistry, 2024, 39(3): 239-257. doi: 10.3866/PKU.DXHX202309093

    10. [10]

      Wenyan Dan Weijie Li Xiaogang Wang . The Technical Analysis of Visual Software ShelXle for Refinement of Small Molecular Crystal Structure. University Chemistry, 2024, 39(3): 63-69. doi: 10.3866/PKU.DXHX202302060

    11. [11]

      Yingchun ZHANGYiwei SHIRuijie YANGXin WANGZhiguo SONGMin WANG . Dual ligands manganese complexes based on benzene sulfonic acid and 2, 2′-bipyridine: Structure and catalytic properties and mechanism in Mannich reaction. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1501-1510. doi: 10.11862/CJIC.20240078

    12. [12]

      Xiaowei TANGShiquan XIAOJingwen SUNYu ZHUXiaoting CHENHaiyan ZHANG . A zinc complex for the detection of anthrax biomarker. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1850-1860. doi: 10.11862/CJIC.20240173

    13. [13]

      Jinfeng Chu Lan Jin Yu-Fei Song . Exploration and Practice of Flipped Classroom in Inorganic Chemistry Experiment: a Case Study on the Preparation of Inorganic Crystalline Compounds. University Chemistry, 2024, 39(2): 248-254. doi: 10.3866/PKU.DXHX202308016

    14. [14]

      Xuyang Wang Jiapei Zhang Lirui Zhao Xiaowen Xu Guizheng Zou Bin Zhang . Theoretical Study on the Structure and Stability of Copper-Ammonia Coordination Ions. University Chemistry, 2024, 39(3): 384-389. doi: 10.3866/PKU.DXHX202309065

    15. [15]

      Shitao Fu Jianming Zhang Cancan Cao Zhihui Wang Chaoran Qin Jian Zhang Hui Xiong . Study on the Stability of Purple Cabbage Pigment. University Chemistry, 2024, 39(4): 367-372. doi: 10.3866/PKU.DXHX202401059

    16. [16]

      Ping Song Nan Zhang Jie Wang Rui Yan Zhiqiang Wang Yingxue Jin . Experimental Teaching Design on Synthesis and Antitumor Activity Study of Cu-Pyropheophorbide-a Methyl Ester. University Chemistry, 2024, 39(6): 278-286. doi: 10.3866/PKU.DXHX202310087

    17. [17]

      Dongju Zhang . Exploring the Descriptions and Connotations of Basic Concepts of Teaching Crystal Structures. University Chemistry, 2024, 39(3): 18-22. doi: 10.3866/PKU.DXHX202304003

    18. [18]

      Hongwei Ma Hui Li . Three Methods for Structure Determination from Powder Diffraction Data. University Chemistry, 2024, 39(3): 94-102. doi: 10.3866/PKU.DXHX202310035

    19. [19]

      Xiaoning TANGJunnan LIUXingfu YANGJie LEIQiuyang LUOShu XIAAn XUE . Effect of sodium alginate-sodium carboxymethylcellulose gel layer on the stability of Zn anodes. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1452-1460. doi: 10.11862/CJIC.20240191

    20. [20]

      Jiaxi Xu Yuan Ma . Influence of Hyperconjugation on the Stability and Stable Conformation of Ethane, Hydrazine, and Hydrogen Peroxide. University Chemistry, 2024, 39(11): 374-377. doi: 10.3866/PKU.DXHX202402049

Metrics
  • PDF Downloads(1)
  • Abstract views(761)
  • HTML views(64)

通讯作者: 陈斌, bchen63@163.com
  • 1. 

    沈阳化工大学材料科学与工程学院 沈阳 110142

  1. 本站搜索
  2. 百度学术搜索
  3. 万方数据库搜索
  4. CNKI搜索
Address:Zhongguancun North First Street 2,100190 Beijing, PR China Tel: +86-010-82449177-888
Powered By info@rhhz.net

/

DownLoad:  Full-Size Img  PowerPoint
Return