Citation: Anjing Liao, Wei Sun, Yaming Liu, Han Yan, Zhi Xia, Jian Wu. Pyrrole and pyrrolidine analogs: The promising scaffold in discovery of pesticides[J]. Chinese Chemical Letters, ;2025, 36(3): 110094. doi: 10.1016/j.cclet.2024.110094 shu

Pyrrole and pyrrolidine analogs: The promising scaffold in discovery of pesticides

Anjing Liao ^a ,
Wei Sun ^a ,
Yaming Liu ^a ,
Han Yan ^a ,
Zhi Xia ^{a, b, *,} ,
Jian Wu ^{a, *,}

a.
State Key Laboratory of Green Pesticide, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Huaxi District, Guiyang 550025, China
b.
College of Chemistry and Chemical Engineering, Guizhou University of Engineering Science, Bijie 551700, China

xz8084696@126.com

jwu6@gzu.edu.cn

Received Date: 7 April 2024
Revised Date: 20 May 2024
Accepted Date: 5 June 2024
Available Online: 6 June 2024

Figures(6)

Pyrrole is a heterocycle with four carbon atoms and a nitrogen atom, which is extensively used in the pesticide and pharmaceutical industries. In addition, it has a series of analogs such as pyrrolidine, pyrroline, and pyrrolidone. Pesticides containing pyrrole and its analogs have been formally marketed as fungicides, including fenpiclonil, fludioxonil, the insecticide chlorfenapyr, and the herbicide fluorochloridone. In this paper, we analyze the structure-activity relationships (SARs) of pesticides containing these structures. We summarize the characteristics possessed by the most highly active pyrrole and its analogs and provide an overview of research on pyrrole compounds with insecticidal, antimicrobial, herbicidal, and antiviral properties in the past 20 years. It is hoped to provide ideas for the development and design of this type compounds in pesticides and to assist researchers in this area.
- Pyrrole,
- Pyrrolidone,
- Agrochemicals,
- Biological activity,
- Structure-activity relationship
1. [1]
  A. Domagala, T. Jarosz, M. Lapkowski, Eur. J. Med. Chem. 100 (2015) 176–187. doi: 10.1016/j.ejmech.2015.06.009
2. [2]
  F.M. Tajabadi, M.R. Campitelli, R.J. Quinn, Springer Sci. Rev. 1 (2013) 141–151. doi: 10.1007/s40362-013-0014-7
3. [3]
  A.L. Dai, Z.G. Zheng, Y.Q. Huang, et al., Heliyon. 8 (2022) e12391. doi: 10.1016/j.heliyon.2022.e12391
4. [4]
  G. Casiraghi, P. Spanu, G. Rassu, L. Pinna, F. Ulgheri, J. Org. Chem. 59 (1994) 2906–2909. doi: 10.1021/jo00089a044
5. [5]
  P. Jouin, B. Castro, D. Nisato, J. Chem. Soc., Perkin Trans. 1. (1987) 1177–1182. doi: 10.1039/P19870001177
6. [6]
  S.C. Xu, M.G. Jiang, Chin. J. Pestic. Sci. 4 (2002) 1–13.
7. [7]
  L.G. Copping, J.J. Menn, Pest Manag. Sci. 56 (2000) 651–676. doi: 10.1002/1526-4998(200008)56:8<651::AID-PS201>3.0.CO;2-U
8. [8]
  E.F. Rogers, F.R. Koniuszy, J.J. Shavel, K. Folkers, J. Am. Chem. Soc. 70 (1948) 3086–3088. doi: 10.1021/ja01189a074
9. [9]
  H. Greger, Planta Med. 72 (2006) 99–113. doi: 10.1055/s-2005-916258
10. [10]
  W.M. Blaney, M.S.J. Simmonds, S.V. Evans, L.E. Fellows, Entomol. Exp. Appl. 36 (1984) 209–216. doi: 10.1111/j.1570-7458.1984.tb03430.x
11. [11]
  M.S.J. Simmonds, W.M. Blaney, L.E. Fellows, J. Chem. Ecol. 16 (1990) 3167–3196. doi: 10.1007/BF00979618
12. [12]
  R. Figliuolo, S. Naylor, J. Wang, J.H. Langenheim, Phytochemistry 26 (1987) 3255–3259. doi: 10.1016/S0031-9422(00)82482-6
13. [13]
  A.B. Attygalle, E.D. Morgan, Chem. Soc. Rev. 1984, 13(3) 245–278. doi: 10.1039/cs9841300245
14. [14]
  J.D. Broadbent, Patent, US4595679 A, 1986.
15. [15]
  A.B. Attygalle, S.C. Xu, K.D. McCormick, et al., Tetrahedron. 49 (1993) 9333–9342. doi: 10.1016/0040-4020(93)80019-P
16. [16]
  J.M. Ligon, D.S. Hill, P.E. Hammer, et al., Pest. Manag. Sci. 56 (2000) 688–695. doi: 10.1002/1526-4998(200008)56:8<688::AID-PS186>3.0.CO;2-V
17. [17]
  D.S. Hill, J.I. Stein, N.R. Torkewitz, et al., Appl. Environ. Microb. 60 (1994) 78–85. doi: 10.1128/aem.60.1.78-85.1994
18. [18]
  M. Koyama, F. Kai, T. Tsuruoka, et al., Patent, EP80051A2, 1983.
19. [19]
  N. Ezaki, M. Koyama, T. Shomura, T. Tsuruoka, S. Inouye, J. Antibiot. 36 (1983) 1263–1267. doi: 10.7164/antibiotics.36.1263
20. [20]
  B. Winblad, Cns Neurosci. Ther. 11 (2006) 169–182.
21. [21]
  C.F. Caley, S.S. Weber, Ann. Pharmacother. 29 (1995) 152–160. doi: 10.1177/106002809502900210
22. [22]
  J.J.V. McMurray, M. Packer, A.S. Desai, et al., New. Engl. J. Med. 371 (2014) 993–1004. doi: 10.1056/NEJMoa1409077
23. [23]
  L.J. Yu, A.L. Dai, W. Zhang, et al., J. Agric. Food Chem. 70 (2022) 10693–10707. doi: 10.1021/acs.jafc.2c02301
24. [24]
  L.J. Yu, S.X. Guo, Y. Wang, et al., J. Agric. Food Chem. 70 (2022) 15726–15736. doi: 10.1021/acs.jafc.2c06189
25. [25]
  P. Sun, Y.Q. Huang, S. Chen, et al., Chin. Chem. Lett. 35 (2024) 109005. doi: 10.1016/j.cclet.2023.109005
26. [26]
  P. Sun, Y.Q. Huang, X.Y. Yang, et al., Front. Plant. Sci. 13 (2023) 1120613. doi: 10.3389/fpls.2022.1120613
27. [27]
  D.G. Kuhn, V.M. Kamhi, J.A. Furch, et al., J. Pestic. Sci. 41 (1994) 279–286. doi: 10.1002/ps.2780410312
28. [28]
  W. Yang, Y. Chen, Y. Zhang, X.B. Gao, Y.F. Zhou, Pestic. Biochem. Phys. 141 (2017) 29–40. doi: 10.1016/j.pestbp.2016.11.003
29. [29]
  B.C. Black, R.M. Hollingworth, K.I. Ahammadsahib, C.D. Kukel, S. Donovan, Pestic. Biochem. Phys. 50 (1994) 115–128. doi: 10.1006/pest.1994.1064
30. [30]
  S. Periasamy, J.F. Deng, M.Y. Liu, Xenobiotica 47 (2017) 833–835. doi: 10.1080/00498254.2016.1236300
31. [31]
  R.W. Addor, S.F. Donovan, R.E. Diehl, Patent, EP484614A, 1992.
32. [32]
  V. Kameswaran, Patent, EP434940 A2, 1991.
33. [33]
  D.G. Kuhn, F.S. Donovan, J.A. Furch, Patent, US5286741A, 1994.
34. [34]
  D.G. Kuhn, F.S. Donovan, J.A. Furch, Patent, US5232980A, 1993.
35. [35]
  D.G. Kuhn, F.S. Donovan, J.A. Furch, Patent, US5286743A, 1994.
36. [36]
  V. Kameswaran, Patent, EP530515A1, 1993.
37. [37]
  D.G. Kuhn, V. Kameswaran, Patent, EP545103A1, 1993.
38. [38]
  A.P. Liu, X.P. Liu, M. Chen, et al., Patent, CN102584667A, 2012.
39. [39]
  A. Liu, M. Tang, S. Yu, et al., Sci. China Chem. 56 (2013) 117–123. doi: 10.1007/s11426-012-4733-4
40. [40]
  P. Zhou, L.X. Zhang, J.H. Ma, et al., Chin. J. Pestic. Sci. 25 (2023) 340–352. doi: 10.3390/socsci12060340
41. [41]
  P. Zhou, J.J. Huang, C.W. He, et al., Chin. J. Pestic. Sci. 24 (2022) 1367–1376. doi: 10.3390/f13091367
42. [42]
  P. Zhou, Q.N. Guo, J. You, et al., Agrochemicals 62 (2023) 17–23.
43. [43]
  G.L. Mao, Y. Yan, Y. Chen, et al., J. Agric. Food Chem. 65 (2017) 6169–6178. doi: 10.1021/acs.jafc.7b02044
44. [44]
  Y. Chen, Y. Yan, Z.F. Ren, et al., J. Agric. Food Chem. 66 (2018) 12527–12535. doi: 10.1021/acs.jafc.8b03591
45. [45]
  Y. Chen, Z. Lei, Y. Zhang, et al., Molecules, 22 (2017) 1058. doi: 10.3390/molecules22071058
46. [46]
  T.X. Li, Y. Chen, H.F. Liu, et al., Molecules, 26 (2021) 4570. doi: 10.3390/molecules26154570
47. [47]
  Q.M. Wang, C.H. Mao, Y. Zhao, R.Q. Huang, F.C. Bi, Patent, CN1891688A, 2005.
48. [48]
  Y. Zhao, Y. Li, X. Ou, et al., J. Agric. Food Chem. 56 (2008) 10176–10182. doi: 10.1021/jf802464d
49. [49]
  Y. Zhao, C. Mao, Y.Q. Li, et al., J. Agric. Food Chem. 56 (2008) 7326–7332. doi: 10.1021/jf801311h
50. [50]
  H. Dai, Y.Q. Li, D. Du, et al., J. Agric. Food Chem. 56 (2008) 10176–10182. doi: 10.1021/jf802464d
51. [51]
  B. Xu, G.C. Ran, Patent, CN105622598 A, 2016.
52. [52]
  J.L. Sun, Patent, CN102731363 A, 2012.
53. [53]
  Y.X. Liu, P.X. Zhang, Y.Q. Li, H.B. Song, Q.M. Wang, Mol. Divers. 18 (2014) 593–598. doi: 10.1007/s11030-014-9515-9
54. [54]
  Q. Ma, Y. Liu, P. Zhang, et al., J. Agric. Food Chem. 62 (2014) 6072–6081. doi: 10.1021/jf501377t
55. [55]
  J.L. Sun, Patent, CN103539716 A, 2014.
56. [56]
  C.H. Mao, Y. Zhao, Y.Q. Li, et al., Chin. J. Org. Chem. 29 (2009) 929–935.
57. [57]
  Y. Li, P. Zhang, Q. Ma, et al., Bioorg. Med. Chem. Lett. 22 (2012) 6858–6861. doi: 10.1016/j.bmcl.2012.09.036
58. [58]
  S.C. Xu, Q. Wang, J.P. Ni, et al., J. Nanjing Agric. Univ. 27 (2004) 6858–6861.
59. [59]
  D. Chou, W. Knauf, M. Maier, et al., Patent, US 20070281976 A1, 2007.
60. [60]
  A.A. Abdelhamid, K.S.M. Salama, A.M. Elsayed, et al., ACS Omega. 7 (2022) 3990–4000. doi: 10.1021/acsomega.1c05049
61. [61]
  A. Yutaka; M. Akihiro; Y. Ikki, et al., Patent, WO2018199208 A1, 2018.
62. [62]
  Á. Cantín, P. Moya, M.A. Miranda, J. Primo, E. Primo-Yúfera, J. Agric. Food Chem. 46 (1998) 4748–4753. doi: 10.1021/jf9800763
63. [63]
  H. Zhao, A. Yang, N. Zhang, et al., J. Agric. Food Chem. 68 (2020) 1588–1595. doi: 10.1021/acs.jafc.9b06755
64. [64]
  Q. Lu, L. Xu, L. Liu, et al., J. Agric. Food Chem. 69 (2021) 14086–14091. doi: 10.1021/acs.jafc.1c05385
65. [65]
  C. Wu, X. Yu, B. Wang, et al., J. Agric. Food Chem. 68 (2020) 9319–9328. doi: 10.1021/acs.jafc.0c04157
66. [66]
  Z.M. Li, B.L. Wang, C.C. Wu, L.X. Xiong, N. Yang, Patent, CN 108689988 A, 2018.
67. [67]
  Y. Zhao, H. Li, P. Sun, et al., Chem. Res. Chin. U. 36 (2020) 1168–1173. doi: 10.1007/s40242-020-0237-5
68. [68]
  M. Jun, M. Tetsuya, Y. Daiei, et al., Patent, WO2008128711, 2008.
69. [69]
  G. Ulrich, M. Jun, M. Tetsuya, et al., Patent, WO2010043315, 2010.
70. [70]
  M. Jun, H. Mamoru, Y. Daiei, et al., Patent, WO2011080211, 2011.
71. [71]
  H. Xu, X. Xiao, X.F. Zhao, Y. Guo, X.J. Yao, Bioorg. Med. Chem. Lett. 21 (2011) 4008–4012. doi: 10.1016/j.bmcl.2011.05.004
72. [72]
  Y. Guo, L. Fan, J. Wang, et al., Tetrahedron. 69 (2013) 774–781. doi: 10.1016/j.tet.2012.10.073
73. [73]
  J. Wang, X. Yu, X. Zhi, H. Xu, Bioorg. Med. Chem. Lett. 24 (2014) 4542–4545. doi: 10.1016/j.bmcl.2014.07.076
74. [74]
  M. Doe, Y. Hirai, T. Kinoshita, et al., Chem. Lett. 33 (2004) 714–715. doi: 10.1246/cl.2004.714
75. [75]
  H. He, X. Qin, F. Dong, et al., Sci. Rep-Uk. 10 (2020) 17999. doi: 10.1038/s41598-020-75053-1
76. [76]
  M. Ito, H. Okui, H. Nakagawa, et al., Biosci. Biotech. Bioch. 66 (2014) 2406–2414.
77. [77]
  W. Zhang, S.X. Guo, Y. Wang, Y, et al., Front. Plant. Sci. 13 (2022) 1086057. doi: 10.3389/fpls.2022.1086057
78. [78]
  Z.G. Zheng, A.L. Dai, Z.C. Jin, Y.R. Chi, J. Wu, J. Agric. Food Chem. 70 (2022) 11019–11030. doi: 10.1021/acs.jafc.1c08383
79. [79]
  B. Fu, L. Xie, L.G. Wu, et al., Patent, CN 106243084, 2016.
80. [80]
  Á. Cantín, P. Moya, M.A. Miranda, J. Primo, E. Primo-Yúfera, J. Agric. Food Chem. 48 (2000) 3682–3688. doi: 10.1021/jf990948g
81. [81]
  T. Seitz, M. Füsslein, J.R. Jansen, et al., Patent, WO2003024220, 2003.
82. [82]
  S. Chen, Y. Zhang, Y. Liu, Q. Wang, J. Agric. Food Chem. 69 (2021) 3601–3606. doi: 10.1021/acs.jafc.0c05558
83. [83]
  M. Jun, H. Mamoru, Y. Daiei, et al., Patent, WO2012035011, 2012.
84. [84]
  Y. Li, Z. Wang, P. Zhang, et al., J. Heterocycl. Chem. 51 (2014) 1410–1414. doi: 10.1002/jhet.1835
85. [85]
  S.J. Xue, C.L. Lu, Chin. J. Org. Chem. 28 (2008) 1083–1086.
86. [86]
  T. Tsze, Patent, US5512537, 1996.
87. [87]
  T. Tsze, Patent, US5681795, 1997.
88. [88]
  G. Meazza, F. Bettarini, P.L. Porta, et al., Pest. Manag. Sci. 60 (2004) 1178–1188. doi: 10.1002/ps.923
89. [89]
  M. Giovanni; B. Franco; C. Paolo; et al., Patent, EP1061072 A1, 2000.
90. [90]
  B. Franco, M. Giovanni, C. Paolo, P. Domenico, Patent, WO2002070476A1, 2002
91. [91]
  R.E. Holm, D.E. Stallard. Weed Sci. 22 (1974) 10–14. doi: 10.1017/s0043174500036419
92. [92]
  H. Huang, C.M. Morgan, R.N. Asolkar, M.E. Koivunen, P.G. Marrone, J. Agric. Food Chem. 58 (2010) 9994–10000. doi: 10.1021/jf102087c
93. [93]
  D. Uwe, H. Hendrik, L. Stefan, et al., Patent, WO2020064260A1, 2020.
94. [94]
  M.M. Lay, A.M. Niland, Pestic. Biochem. Phys. 19 (1983) 337–343. doi: 10.1016/0048-3575(83)90062-7
95. [95]
  S. Yamato, T. Fusaka, Y. Tanaka, J. Pestic. Sci. 30 (2005) 384–389. doi: 10.1584/jpestics.30.384
96. [96]
  G.F. Hao, Y. Zuo, S.G. Yang, G.F. Yang, Chimia (Aarau) 65 (2011) 961. doi: 10.2533/chimia.2011.961
97. [97]
  K.M. Moon, E.B. Kwon, B. Lee, C.Y. Kim, Molecules 25 (2020) 2754. doi: 10.3390/molecules25122754
98. [98]
  Y. Zou, S.G. Yang, Y.P. Luo, T. Ying, et al., Bioorg. Med. Chem. 21 (2013) 3245–3255. doi: 10.1016/j.bmc.2013.03.056
99. [99]
  G.F. Hao, C.G. Zhan, G.F. Yang, Fut. Med. Chem. 6 (2014) 597–599. doi: 10.4155/fmc.14.29
100. [100]
  L. Zhang, J. Wan, G.F. Yang, Bioorg. Med. Chem. 12 (2004) 6183–6191. doi: 10.1016/j.bmc.2004.08.046
101. [101]
  L.X. Zhao, J.J. Hu, Z.X. Wang, et al., Pestic. Biochem. Phys. 170 (2020) 104684. doi: 10.1016/j.pestbp.2020.104684
102. [102]
  L.X. Zhao, J.F. Peng, J.J. Hu, et al., J. Mol. Struct. 1258 (2022) 132670. doi: 10.1016/j.molstruc.2022.132670
103. [103]
  M. Ikeguchi, M. Sawaki, H. Yoshii, K. Maeda, Y. Morishima, J. Pestic. Sci. 25 (2000) 107–116. doi: 10.1584/jpestics.25.107
104. [104]
  A. Lars, F. Jens, D. Hansjoerg, et al., Patent, WO2022200208A1, 2022.
105. [105]
  N.D. Davis, U.L. Diener, G. Morgan-Jones, Appl. Environ. Microb. 34 (1977) 155–157. doi: 10.1128/aem.34.2.155-157.1977
106. [106]
  S. Chen, Y. Kang, M. Zhang, et al., Environ. Exp. Bot. 112 (2015) 1–15. doi: 10.1016/j.envexpbot.2014.11.009
107. [107]
  S. Chen, S. Qiang, Pestic Biochem. Phys. 143 (2017) 252–257. doi: 10.1016/j.pestbp.2017.01.003
108. [108]
  S. Chen, X. Xu, X. Dai, C. Yang, S. Qiang, Bba-Bioenerget. 1767 (2007) 306–318. doi: 10.1016/j.bbabio.2007.02.007
109. [109]
  Q. Geng, J. Xie, X. Wang, et al., J. Agric. Food Chem. 66 (2018) 12198–12205. doi: 10.1021/acs.jafc.8b04812
110. [110]
  S. Qiang, S.G. Cheng, X.B. Dai, Y.F. Dong, Patent, CN 1752075A, 2005.
111. [111]
  S. Qiang, Q. Yao, Patent, CN 105130871A, 2015.
112. [112]
  B.F. Han, Q.M. Shi, X.F. Wang, et al., Chin. Chem. Lett. 23 (2012) 1023–1026. doi: 10.1016/j.cclet.2012.07.002
113. [113]
  Y.Q. Zhu, X.M. Zou, F.Z. Hu, et al., J. Agric. Food Chem. 53 (2005) 9566–9570. doi: 10.1021/jf051510l
114. [114]
  Y.Q. Zhu, C.S. Yao, X.M. Zou, et al., Molecules 10 (2005) 427–434. doi: 10.3390/10020427
115. [115]
  Y.Q. Zhu, X.K. Si, X.M. Zou, B. Liu, H.Z. Yang, Chin. J. Org. Chem. 27 (2007) 385–390.
116. [116]
  Y.Q. Zhu, R. Zhu, Y.W. Yuan, et al., Chin. J. Org. Chem. 30 (2010) 1207–1211.
117. [117]
  Y.X. Liu, Z.P. Cui, Y.H. Li, Y.C. Gu, Q.M. Wang, J. Heterocycl. Chem. 51 (2014) E209–E215.
118. [118]
  Y.X. Liu, Z.P. Cui, Y.H. Li, Y.C. Gu, Q.M. Wang, J. Heterocycl. Chem. 51 (2014) E197–E201.
119. [119]
  X.J. Zhu, L. Huang, X.F. Wang, et al., Chin. J. Org. Chem. 29 (2009) 1784–1789.
120. [120]
  Z.Y. Zhu, Q.M. Shi, B.F. Han, et al., Bull. Korean Chem. Soc. 31 (2010) 2467–2472. doi: 10.5012/bkcs.2010.31.9.2467
121. [121]
  X.F. Wang, T.F. Si, Q.B. Li, et al., Arkivoc. (2010) 31–48. doi: 10.3998/ark.5550190.0011.203
122. [122]
  T.F. Si, F.G. Meng, X.F. Wang, et al., Chin. J. Org. Chem. 31 (2011) 521–527.
123. [123]
  Y.X. Liu, H.P. Zhao, H.B. Song, Y.C. Gu, Q.M. Wang, J. Heterocycl. Chem. 51 (2014) E25–E33.
124. [124]
  M. Chen, C.W. Geng, L. Han, et al., New J. Chem. 45 (2021) 5621–5630. doi: 10.1039/d1nj00119a
125. [125]
  J. Desouza, J. Raaijmakers, FEMS Microbiol. Ecol. 43 (2003) 21–34. doi: 10.1016/S0168-6496(02)00414-2
126. [126]
  P. Leroux, C. Lanen, R. Fritz, Pest Manage. Sci. 36 (2006) 255–261.
127. [127]
  C. Lamberth, Bioact. Heterocycl. Compd. Cl. (2012) 155–162. doi: 10.1002/9783527664412.ch13
128. [128]
  C. Pillonel, T. Meyer, Pest Manage. Sci. 49 (1997) 229–236. doi: 10.1002/(SICI)1096-9063(199703)49:3<229::AID-PS525>3.0.CO;2-T
129. [129]
  H.L. Xu, J. Su, Z.S. Wang, et al., Chin. J. Org. Chem. 41 (2021) 2560–3570.
130. [130]
  J.F. Chollet, F. Rocher, C. Jousse, et al., Pest Manage. Sci. 60 (2004) 1063–1072. doi: 10.1002/ps.906
131. [131]
  J.F. Chollet, F. Rocher, C. Jousse, et al., Pest Manage. Sci. 61 (2004) 377–382.
132. [132]
  T.T. Yao, D.X. Xiao, Z.S. Li, et al., J. Agric. Food Chem. 65 (2017) 5397–5403. doi: 10.1021/acs.jafc.7b01251
133. [133]
  X.D. An, J. Xiao, B. Qiu, S. Yang, Patent, CN115010641A, 2022.
134. [134]
  M.Z. Zhang, Y. Zhang, J.Q. Wang, W.H. Zhang, Molecules 21 (2016) 1387. doi: 10.3390/molecules21101387
135. [135]
  X. Yu, P. Teng, Y.L. Zhang, et al., Fitoterapia 127 (2018) 387–395. doi: 10.1016/j.fitote.2018.03.013
136. [136]
  S.G. Zhang, C.G. Liang, Y.Q. Sun, et al., Mol. Diversity. 23 (2019) 915–925. doi: 10.1007/s11030-019-09920-z
137. [137]
  S.G. Zhang, X. Tan, C.G. Liang, W.H. Zhang, J. Heterocycl. Chem. 58 (2021) 450–458. doi: 10.1002/jhet.4180
138. [138]
  W.Q. Xu, M. Chen, K.Y. Wang, et al., Molecules 21 (2016) 355. doi: 10.3390/molecules21030355
139. [139]
  M. Chen, L. Zhang, A. Lu, et al., Bioorg. Med. Chem. Lett. 30 (2020) 127519. doi: 10.1016/j.bmcl.2020.127519
140. [140]
  G.H. Lu, H.B. Chu, M. Chen, C.L. Yang, Chin. Chem. Lett. 25 (2014) 61–64. doi: 10.1016/j.cclet.2013.10.007
141. [141]
  K.L. Obydennov, L.A. Khamidullina, A.N. Galushchinskiy, et al., J. Agric. Food Chem. 66 (2018) 6239–6245. doi: 10.1021/acs.jafc.8b02151
142. [142]
  C.L. Yang, X.F. Wang, L.L. Feng, et al., Patent, CN 103183628 A, 2013.
143. [143]
  A. Lu, T. Wang, H. Hui, et al., J. Agric. Food Chem. 66 (2018) 6239–6245. doi: 10.1021/acs.jafc.8b02151
144. [144]
  F. Liu, X. Cao, L. Xing, et al., Chem. Biodivers. 20 (2023) e202201103. doi: 10.1002/cbdv.202201103
145. [145]
  P.Y. Wang, L. Chen, J. Zhou, et al., J. Saudi Chem. Soc. 21 (2017) 315–323. doi: 10.1016/j.jscs.2016.10.002
146. [146]
  J.G. Yang, F.L. Wang, J.H. Bi, et al., Patent, CN103387529A, 2013.
147. [147]
  L. Mathilde Denise, S. Claudio, D.M. Alain, et al., Patent, WO2015128321A1, 2015.
148. [148]
  C. Camilla; W. Sebastian Volker; B. Carla; Patent, US20110263431A1 2011.
149. [149]
  Y.N. Bubnov, Y.Y. Spiridonov, N.Y. Kuznetsov, Russ. Chem. Bull. 67 (2018) 345–358. doi: 10.1007/s11172-018-2080-0
150. [150]
  M.G. De los Santos, M. Cua-Basulto, A. Huepalcalco, et al., Molecules 27 (2022) 8466. doi: 10.3390/molecules27238466
1. [1]
  Ping Sun , Yuanqin Huang , Shunhong Chen , Xining Ma , Zhaokai Yang , Jian Wu . Indole derivatives as agrochemicals: An overview. Chinese Chemical Letters, 2024, 35(7): 109005-. doi: 10.1016/j.cclet.2023.109005
2. [2]
  Wei Sun , Anjing Liao , Li Lei , Xu Tang , Ya Wang , Jian Wu . Research progress on piperidine-containing compounds as agrochemicals. Chinese Chemical Letters, 2025, 36(1): 109855-. doi: 10.1016/j.cclet.2024.109855
3. [3]
  Ali Dai , Zhiguo Zheng , Liusheng Duan , Jian Wu , Weiming Tan . Small molecule chemical scaffolds in plant growth regulators for the development of agrochemicals. Chinese Chemical Letters, 2025, 36(4): 110462-. doi: 10.1016/j.cclet.2024.110462
4. [4]
  Tao Yu , Vadim A. Soloshonok , Zhekai Xiao , Hong Liu , Jiang Wang . Probing the dynamic thermodynamic resolution and biological activity of Cu(Ⅱ) and Pd(Ⅱ) complexes with Schiff base ligand derived from proline. Chinese Chemical Letters, 2024, 35(4): 108901-. doi: 10.1016/j.cclet.2023.108901
5. [5]
  Qin Cheng , Ming Huang , Qingqing Ye , Bangwei Deng , Fan Dong . Indium-based electrocatalysts for CO₂ reduction to C1 products. Chinese Chemical Letters, 2024, 35(6): 109112-. doi: 10.1016/j.cclet.2023.109112
6. [6]
  A-Yang Wang , Sheng-Hua Zhou , Mao-Yin Ran , Xin-Tao Wu , Hua Lin , Qi-Long Zhu . Regulating the key performance parameters for Hg-based IR NLO chalcogenides via bandgap engineering strategy. Chinese Chemical Letters, 2024, 35(10): 109377-. doi: 10.1016/j.cclet.2023.109377
7. [7]
  Yi-Ru Bai , Qing-Chuan Duan , Dong-Jie Seng , Ying Xu , Hong-Bo Ren , Jie Zhang , Dan-Dan Shen , Li Yang , Hong-Min Liu , Shuo Yuan . A comprehensive review of small molecule drugs approved by the FDA in 2024: Advance and prospect. Chinese Chemical Letters, 2025, 36(10): 111025-. doi: 10.1016/j.cclet.2025.111025
8. [8]
  Haoran Xu , Jiaqi Fan , Jiwei Liu , Qi Wei , Ruoshui Li , Pengcheng Yuan , Bing Xiao , Ying Piao , Wenjing Sun , Jiajia Xiang , Shiqun Shao , Zhuxian Zhou , Youqing Shen , Nigel K.H. Slater , Jianbin Tang . Tetra-branched ionizable lipids enhance the stability and transfection efficiency of lipid nanoparticles for mRNA delivery. Chinese Chemical Letters, 2025, 36(11): 110833-. doi: 10.1016/j.cclet.2025.110833
9. [9]
  Chao Chen , Wang Geng , Ke Li , Qiong Lei , Zhichao Jin , Xiuhai Gan . Pyridazine: A privileged scaffold in the development of 21^st-century pesticides. Chinese Chemical Letters, 2025, 36(8): 110902-. doi: 10.1016/j.cclet.2025.110902
10. [10]
  Tingting Du , Siyu Lu , Zongnan Zhu , Mei Zhu , Yan Zhang , Jian Zhang , Jixiang Chen . Pyrazole derivatives: Recent advances in discovery and development of pesticides. Chinese Chemical Letters, 2025, 36(9): 110912-. doi: 10.1016/j.cclet.2025.110912
11. [11]
  Jia JI , Zhaoyang GUO , Wenni LEI , Jiawei ZHENG , Haorong QIN , Jiahong YAN , Yinling HOU , Xiaoyan XIN , Wenmin WANG . Two dinuclear Gd(Ⅲ)-based complexes constructed by a multidentate diacylhydrazone ligand: Crystal structure, magnetocaloric effect, and biological activity. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 761-772. doi: 10.11862/CJIC.20240344
12. [12]
  Jian Song , Shenghui Wang , Qiuge Liu , Xiao Wang , Shuo Yuan , Hongmin Liu , Saiyang Zhang . N-Benzyl arylamide derivatives as novel and potent tubulin polymerization inhibitors against gastric cancers: Design, structure–activity relationships and biological evaluations. Chinese Chemical Letters, 2025, 36(2): 109678-. doi: 10.1016/j.cclet.2024.109678
13. [13]
  Ruizhi Duan , Xiaomei Wang , Panwang Zhou , Yang Liu , Can Li . The role of hydroxyl species in the alkaline hydrogen evolution reaction over transition metal surfaces. Acta Physico-Chimica Sinica, 2025, 41(9): 100111-0. doi: 10.1016/j.actphy.2025.100111
14. [14]
  Haiying Jiang , Liuhong Song , Yangyang Cheng , Kefen Yue , Mingli Peng , Huilin Guo . Ph―C≡C―Cu_2.5的力致变色现象探究——推荐一个物理化学实验. University Chemistry, 2025, 40(8): 249-254. doi: 10.12461/PKU.DXHX202410003
15. [15]
  Siran Wang , Yinuo Wang , Yilong Zhao , Dazhen Xu . Advances in the Application and Preparation of Rhodanine and Its Derivatives. University Chemistry, 2025, 40(5): 318-327. doi: 10.12461/PKU.DXHX202407033
16. [16]
  Zhuwen Wei , Jiayan Chen , Congzhen Xie , Yang Chen , Shifa Zhu . Divergent de novo construction of α-functionalized pyrrole derivatives via coarctate reaction. Chinese Chemical Letters, 2024, 35(12): 109677-. doi: 10.1016/j.cclet.2024.109677
17. [17]
  Yao HUANG , Yingshu WU , Zhichun BAO , Yue HUANG , Shangfeng TANG , Ruixue LIU , Yancheng LIU , Hong LIANG . Copper complexes of anthrahydrazone bearing pyridyl side chain: Synthesis, crystal structure, anticancer activity, and DNA binding. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 213-224. doi: 10.11862/CJIC.20240359
18. [18]
  Yingyue ZHANG , Liuqing KANG , Yating YANG , Xiaofen GUAN , Wenmin WANG . Crystal structure and antibacterial activity of two Gd₂ complexes based on polydentate Schiff-base ligands. Chinese Journal of Inorganic Chemistry, 2025, 41(9): 1867-1877. doi: 10.11862/CJIC.20250100
19. [19]
  Peipei CUI , Yawen ZHENG , Pan LI , Peiyan GUAN , Zhaohong QIAN . Praseodymium-organic framework with 4, 4′-oxybis(benzoic acid): Rare broken layer structure, antibacterial activity, and sensing for Cd²⁺ ions. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1641-1649. doi: 10.11862/CJIC.20250152
20. [20]
  Jiarong ZHU , Xiaohua ZHANG , Xinting XIONG , Xuliang NIE , Xiuying SONG , Miaomiao ZHANG , Dayong PENG , Xiuguang YI . Crystal structure, Hirshfeld surface analysis, and antifungal activity of five complexes based on 2,5-bis(carboxymethoxy)terephthalic acid. Chinese Journal of Inorganic Chemistry, 2025, 41(11): 2358-2370. doi: 10.11862/CJIC.20250150

Get Citation

PDF

XML

Metrics

PDF Downloads(3)
Abstract views(1233)
HTML views(30)

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