Skip to main content
SpringerLink
Log in

Design, synthesis, and biological evaluation of 2-benzylpyrroles and 2-benzoylpyrroles based on structures of insecticidal chlorfenapyr and natural pyrrolomycins

  • Full-Length Paper
  • Published:
Molecular Diversity Aims and scope Submit manuscript

Abstract

Based on structures of insecticidal chlorfenapyr and antibiotic natural pyrrolomycins, a series of new 2-benzylpyrroles and 2-benzoylpyrroles (with or without ethoxymethyl group on the nitrogen of pyrrole) were designed and synthesized. These compounds or their parent compounds possess weak acidity and high lipophilicity, the two characteristic properties for uncouplers of oxidative phosphorylation; therefore, they are expected to have insecticidal and acaricidal activity. The bioassay result verified that both 2-benzylpyrroles 17 and 2-benzoylpyrroles 19 had varied degrees of insecticidal activity against oriental armyworm depending on the substituents on the benzene ring, but they did not give any acaricidal activity. Conversely, most N-alkylated compounds 18 and 20 exhibited both insecticidal activity and acaricidal activity, of which compound 18i [4-bromo-2-(2,4-dichlorobenzyl)-1-(ethoxymethyl) -5-(trifluoromethyl) - 1\(H\)-pyrrole-3-carbonitrile] has IC\(_{50}\) as low as 10–20 mg L\(^{-1}\) on both activities.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Scheme 1
Scheme 2

Similar content being viewed by others

Notes

  1. CCDC 960562 (for 20c) contains the supplementary crystallographic data. The data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.

  2. The insecticidal, acaricidal, and fungicidal activity screening procedure in detail can be found in the Supplementary Material.

References

  1. Addor RW, Babcock TJ, Black B et al (1999) Insecticidal pyrroles: discovery and overview. In: Synthesis and chemistry of agrochemicals III. ACS Symposium Series 504, chap 25. American Chemical Society, Washington, pp 283–297

  2. Koyama M, Kodama Y, Tsurouoka T, Ezaki N, Niwa T, Inouye S (1981) Structure and synthesis of pyrrolomycin A, a chlorinated nitro-pyrrole antibiotic. J Antibiot 34:1569–1576. doi:10.7164/antibiotics.34.1569

    Article  CAS  PubMed  Google Scholar 

  3. Ezaki N, Koyama M, Shomura T, Tsuruoka T, Inouye S (1983) Pyrrolomycins C, D and E, new members of pyrrolomycins. J Antibiot 36:1263–1267. doi:10.7164/antibiotics.36.1263

    Article  CAS  PubMed  Google Scholar 

  4. Carter GT, Nietsche JN, Goodman JJ, Torrey MJ, Dunne TS, Borders DB, Testa RT (1987) LL-F42248\(\alpha \), a novel chlorinated pyrrole antibiotic. J Antibiot 40:233–236. doi:10.7164/antibiotics.40.233

    Google Scholar 

  5. Nakamura H, Shiomi K, Iinuma H, Naganawa H, Obata T, Takeuchi T, Umezawa H (1987) Isolation and characterization of a new antibiotic, dioxapyrrolomycin, related to pyrrolomycins. J Antibiot 40:899–903. doi:10.7164/antibiotics.40.899

    Article  CAS  PubMed  Google Scholar 

  6. Yano K, Oono J, Mogi K, Asaoka T, Nakashima T (1987) Pyrroxamycin, a new antibiotic taxonomy, fermentation, isolation, structure determination and biological properties. J Antibiot 40:961–969. doi:10.7164/antibiotics.40.961

    Article  CAS  PubMed  Google Scholar 

  7. Brown DG, Diehl RE, Siddens JK, Wright DP Jr. (1988) Arylpyrrole insecticidal, acaricidal and nematicidal agents and methods for the preparation thereof. US 5010098, 23 June 1988

  8. Lovell JB, Wrigh DP Jr., Gard IE, Miller TP, Treacy MF, Addor RW, Kamhi VM (1990) AC 303630, an insecticide/acaricide from a novel class of chemistry. In: Brighton Crop Protection Conference, pests and diseases, vol 1. British Crop Protection Council, Brighton, pp 37–40

  9. Miller TP, Treacy MF, Gard IE, Lovell JB, Wright DP Jr., Addor RW, Kamhi VM (1990) AC 303630, summary of 1988–1989 field trial results. In: Brighton Crop Protection Conference, pests and diseases, vol 1. British Crop Protection Counci, Brighton, pp 41–45

  10. Black BC, Hollingworth RM, Ahammadsahib KI, Kukel CD, Donovan S (1994) Insecticidal action and mitochondrial uncoupling activity of AC-303, 630 and related halogenated pyrroles. Pestic Biochem Physiol 50(2):115–128. doi:10.1006/pest.1994.1064

    Google Scholar 

  11. Weinbach EC, Garbus J (1969) Mechanism of action of reagents that uncouple oxidative phosphorylation. Nature 221:1016–1018. doi:10.1038/2211016a0

    Article  CAS  PubMed  Google Scholar 

  12. Brenner DG, Cavolowsky KM, Shepard KL (1985) Imino-bridged heterocycles. IV. A facile synthesis of sulfenimines derived from diaryl ketones. J Heterocycl Chem 22(3):805–8

    Article  CAS  Google Scholar 

  13. Park KH, Kurth MJ (1999) An uncatalyzed cyclo-elimination process for the release of N3-alkylated hydantoins from solid-phase: synthesis of novel isoxazoloimidazolidinediones. Tetrahedron Lett 40:5841–5844. doi:10.1016/S0040-4039(99)01145-4

    Article  CAS  Google Scholar 

  14. Zhao X, Wei X, Chen X, Wang Y, Meng J, Wang S (2002) Synthesis and crystal structure of benzyl-\(N\)-(diphenylmethylene)-glycine ethyl ester. J Mol Struct 609(1–3):195–198. doi:10.1016/S0022-2860(01)00977-2

    Google Scholar 

  15. Tian WS, Luo YR, Chen Y (1993) A convenient synthesis of 2-trifluoromethylpyrroles via base-promoted cyclocondensation of trifluoromethyloxazolones with electron-deficient alkenes. J Chem Soc 2:101–102. doi:10.1039/C39930000101

    Google Scholar 

  16. Knapp P, William JR (1996) Manufacture of 4-ary1-2- perfluoroalky1-3-oxazolin-5-one from arylglycine. CN 1132749, 09 Oct 1996

  17. Doehner RF, Barton JM (1995) Alkoxymethylation of pyrroles. CN 1106798, 15 Aug 1995

  18. Fu Q, Zhang XM, Yao W, Kong XL, Lu Q (2006) Synthesis of chlorfenapyr. Nongyao 45(6):385–386

    CAS  Google Scholar 

  19. Liu AP, Tang M, Yu SY, Liu XP, Wang XG, Pei H, Wu DX, Hu L, Ou XM, Huang MZ (2013) Synthesis, insecticidal and acaricidal activities of novel 2-arylpyrroles. Sci China Chem 56(1):117–123. doi:10.1007/s11426-012-4733-4

    Article  CAS  Google Scholar 

Download references

Acknowledgments

This work was supported by the National Key Project for Basic Research (2010CB126106) and the National Natural Science Foundation of China (21072109) and the National Key Technology Research and Development Program (2011BAE06B05).

Author information

Authors and Affiliations

  1. State Key Laboratory of Elemento-Organic Chemistry, Research Institute of Elemento-Organic Chemistry, Nankai University, Tianjin , 300071, People’s Republic of China

    Yu-Xiu Liu, Peng-Xiang Zhang, Yong-Qiang Li, Hai-Bin Song & Qing-Min Wang

Authors
  1. Yu-Xiu Liu
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Peng-Xiang Zhang
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Yong-Qiang Li
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Hai-Bin Song
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Qing-Min Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Qing-Min Wang.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (doc 2970 KB)

Rights and permissions

Reprints and permissions

About this article

Cite this article

Liu, YX., Zhang, PX., Li, YQ. et al. Design, synthesis, and biological evaluation of 2-benzylpyrroles and 2-benzoylpyrroles based on structures of insecticidal chlorfenapyr and natural pyrrolomycins. Mol Divers 18, 593–598 (2014). https://doi.org/10.1007/s11030-014-9515-9

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11030-014-9515-9

Keywords

Search

Navigation