(2E,2′E)-2,2′-(1,2,4-Thiadiazole-3,5-diyl)bis[3-arylacrylonitriles]: Synthesis and Antidote Activity Towards 2,4-D Herbicide

被引：2
|
作者：
Dakhno, P. G. [1 ]
Dotsenko, V. V. [1 ,2 ]
Strelkov, V. D. [1 ,2 ]
Vasilin, V. K. [3 ]
Aksenov, N. A. [2 ]
Aksenova, I. V. [2 ]
机构：
[1] Kuban State Univ, Krasnodar 350040, Russia
[2] North Caucasus Fed Univ, Stavropol 355009, Russia
[3] Kuban State Technol Univ, Krasnodar 350072, Russia
来源：
RUSSIAN JOURNAL OF GENERAL CHEMISTRY | 2022年 / 92卷 / 12期
关键词：
cyanothioacetamide; 2-cyanothioacrylamides; diethyl sulfoxide; oxidative dimerization of thioamides; 1; 2; 4-thiadiazoles; herbicide antidotes; 3,5-DISUBSTITUTED 1,2,4-THIADIAZOLES; THIOAMIDES; CYANOTHIOACETAMIDE; CHOLINESTERASE; DERIVATIVES; CONVENIENT; INHIBITORS; OXIDATION; BLOCKERS; SYSTEM;
D O I：
10.1134/S1070363222120337
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Oxidation of (E)-3-aryl-2-cyanothioacrylamides under the action of the Et2S(O)-HCl system leads to the formation of (2E,2 ' E)-2,2 '-(1,2,4-thiadiazole-3,5-diyl)bis[3-arylacrylonitriles] in 54-91% yields. Structure of the obtained compounds was confirmed by the two-dimensional NMR spectroscopy data. A plausible reaction mechanism was discussed. Two compounds showed a pronounced antidote effect against 2,4-D herbicide in a laboratory experiment on sunflower seedlings in the absence of growth-stimulating activity.
引用
收藏
页码：2822 / 2831
页数：10
相关论文
共 50 条
  • [21] Antiviral stereoisomers of 3,5-bis(2-hydroxybut-3-en-1-yl)-1,2,4-thiadiazole from the roots of Isatis indigotica
    Chen, Ming-Hua
    Lin, Sheng
    Wang, Ya-Nan
    Zhu, Cheng-Gen
    Li, Yu-Huan
    Jiang, Jian-Dong
    Shi, Jian-Gong
    CHINESE CHEMICAL LETTERS, 2016, 27 (05) : 643 - 648
  • [22] Synthesis of (E)-diethyl 6,6′-(diazene-1,2-diyl)bis(5-cyano-2-methyl-4-phenylnicotinates), a new type of 2,2′-azopyridine dyes
    Botelho da Silva, Daniel
    Samadi, Abdelouahid
    Infantes, Lourdes
    do Carmo Carreiras, Maria
    Marco-Contelles, Jose
    TETRAHEDRON LETTERS, 2010, 51 (48) : 6278 - 6281
  • [23] Synthesis and Structure of (2E)-3-Aryl(hetaryl)-2-[5-bromo-4-aryl(hetaryl)-1,3-thiazol-2-yl]acrylonitriles
    Pakholka, N. A.
    Abramenko, V. L.
    Dotsenko, V. V.
    Aksenov, N. A.
    Aksenova, I., V
    Krivokolysko, S. G.
    RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2021, 91 (03) : 357 - 368
  • [24] Synthesis and in-vitro anticancer activity of 3,5-bis(indolyl)-1,2,4-thiadiazoles
    Kumar, Dalip
    Kumar, N. Maruthi
    Chang, Kuei-Hua
    Gupta, Ritika
    Shah, Kavita
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2011, 21 (19) : 5897 - 5900
  • [25] 2-[(2E)-2-(3-chloro-2-fluorobenzylidene)hydrazinyl]pyridine: Synthesis, spectroscopic, structural properties, biological activity and theoretical analysis
    Ozcelik, Nefise
    Tunc, Tuncay
    Celik, Raziye Catak
    Erzengin, Mahmut
    Ozisik, Haci
    JOURNAL OF MOLECULAR STRUCTURE, 2021, 1227
  • [26] N-Chlorosuccinimide is a convenient oxidant for the synthesis of 2,4-disubstituted 1,2,4-thiadiazolidine-3,5-diones
    Nasim, Shama
    Crooks, Peter A.
    TETRAHEDRON LETTERS, 2009, 50 (03) : 257 - 259
  • [27] Mechanosynthesis of 2,2′-((1E,1′E)-(2,5-bis(octyloxy)-1,4-phenylene)bis(ethene-2,1-diyl))bis(6-bromoquinoline): optical, electroluminescence, electrical, electrochemical, and morphological studies
    Angel Amado-Briseno, Miguel
    Javier Hernandez-Ortiz, Oscar
    Veloz Rodriguez, Maria Aurora
    Aleman Ayala, Karina
    del Pozo Melero, Gonzalo
    Romero Herrero, Beatriz
    Hernandez Zanabria, Angelica Guadalupe
    Espinosa Roa, Arian
    Angeles Vazquez-Garcia, Rosa
    JOURNAL OF MATERIALS SCIENCE-MATERIALS IN ELECTRONICS, 2022, 33 (01) : 126 - 138
  • [28] SYNTHESIS OF NEW [1,2,4] TRIAZOLO [3,2-b] [2,4] BENZOTHIAZEPINES
    Davoodnia, A.
    Roshani, M.
    Monfared, A.
    Tavakoli-Hoseini, N.
    INDIAN JOURNAL OF HETEROCYCLIC CHEMISTRY, 2009, 19 (01) : 91 - 92
  • [29] Comparative Study of the Photocatalytic Degradation of the Herbicide 2,4-D Using WO3/TiO2 and Fe2O3/TiO2 as Catalysts
    Macias-Tamez, R.
    Villanueva-Rodriguez, M.
    Ramos-Delgado, N. A.
    Maya-Trevino, L.
    Hernandez-Ramirez, A.
    WATER AIR AND SOIL POLLUTION, 2017, 228 (10)
  • [30] Synthesis, Crystal Structure, and Antibacterial Activity of 1,2,4-Triazoles and 1,2,4-Triazol-3-one
    Ben Salah, Bochra
    Chaari, Najla
    Rekik, Awatef
    Ben Hsouna, Anis
    Trigui, Mohamed
    Kossentini, Mohamed
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2015, 52 (06) : 1769 - 1775
12345