Skip to main content
Log in

Insect growth regulatory activity of carvacrol-based 1,3,4-thiadiazoles and 1,3,4-oxadiazoles

  • Original Article
  • Published:
Molecular Diversity Aims and scope Submit manuscript

Abstract

Abstract 

In designing of novel insect growth regulators (IGRs), biologically occurring carvacrol has been structurally modified to thiadiazole and oxadiazole moieties. Two series of carvacrol analogs containing 1,3,4-thiadiazole (VIIIa–e) and 1,3,4-oxadiazole (IXa–e) derivatives are designed and synthesized. Their structures are confirmed by FT-IR, \(^{1}\text {H}\) NMR, \(^{13}\)C NMR and LC-MS. IGR activity is tested against Spodoptera litura. Several analogs displayed IGR activity against this insect pest. Compounds VIIIe and IXe displayed relatively good IGR activity with \(\text {GI}_{50 }\)values 117.43 and 108.83 ppm against Spodoptera litura, respectively.

Graphical Abstract

Synthesis, characterization and evaluation of carvacrol-based 1,3,4-thiadiazole and 1,3,4-oxadiazole derivatives as potent insect growth regulators (IGRs).

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

Access this article

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

Instant access to the full article PDF.

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Scheme 1
Scheme 2

Similar content being viewed by others

References

  1. Tohnishi M, Nakao H, Furuya T, Seo A, Kodama H, Tsubata K, Fujioka S, Kodama H, Hirooka T, Nishimatsu T (2005) Flubendiamide, a novel insecticide highly active against lepidopterous insect pests. J Pest Sci 30:354–360

    Article  CAS  Google Scholar 

  2. Oerke EC, Dehne HW (2004) Safeguarding production–losses in major crops and the role of crop protection. Crop Protect 23:275–285. https://doi.org/10.1016/j.cropro.2003.10.001

    Article  Google Scholar 

  3. Oerke EC (2006) Crop losses to pests. J Agric Sci 144:31–43. https://doi.org/10.1017/S0021859605005708

    Article  Google Scholar 

  4. Bassil KL, Vakil C, Sanborn M, Cole DC, Kaur JS, Kerr KJ (2007) Cancer health effects of pesticides systematic review. Can Fam Phys 53:1704–1711

    CAS  Google Scholar 

  5. Kanavouras K, Tzatzarakis MN, Mastorodemos V, Plaitakis A, Tsatsakis AM (2011) A case report of motor neuron disease in a patient showing significant level of DDTs, HCHs and organophosphate metabolites in hair as well as levels of hexane and toluene in blood. Toxicol Appl Pharmacol 256:399–404. https://doi.org/10.1016/j.taap.2011.07.022

    Article  PubMed  CAS  Google Scholar 

  6. Clark DA, Lahm GP, Smith BK, Barry JD, Clagg DG (2008) Synthesis of insecticidal fluorinated anthranilic diamides. Bio Med Chem 16:3163–3170. https://doi.org/10.1016/j.bmc.2007.12.017

    Article  CAS  Google Scholar 

  7. Sun J, Zhou Y (2015) Design, synthesis, and insecticidal activity of some novel diacylhydrazine and acylhydrazone derivatives. Molecules 20:5625–5637. https://doi.org/10.3390/molecules20045625

    Article  PubMed  CAS  Google Scholar 

  8. Zade CM, Pete UD, Patil SS, Bhosale JD, Hadole CD, Kadam MS, Bendre RS (2012) Design and development of novel insect growth regulators: synthesis, characterization and effect of benzoyl thymyl thioureas and ureas on total haemocyte count of Dysdercus koenigii. J Environ Sci Health Part B 47:136–143

    Article  CAS  Google Scholar 

  9. Zade CM., Pete UD, Kadam MS, & Bendre RS (2012) Development of novel insect growth regulators: effect of 1-(substitutedbenzoyl)-3-[(2\(\prime \)-Isopropyl-5\(\prime \)-Methylphenoxy) Acetamino] Thiourea and urea derivatives on total haemocyte count of Dysdercus koenigii. In: Chemistry for sustainable development, Springer, Dordrecht, pp 69–79

  10. Bendre RS, Rajput JD, Bagul SD, Karandikar PS (2016) Outlooks on medicinal properties of eugenol and its synthetic derivatives. Nat Prod Chem Rese 4:212. https://doi.org/10.4172/2329-6836.1000212

    Article  CAS  Google Scholar 

  11. Fan Z, Shi Z, Zhang H, Liu X, Bao L, Ma L, Zuo X, Zheng Q, Mi N (2009) Synthesis and biological activity evaluation of 1, 2, 3-thiadiazole derivatives as potential elicitors with highly systemic acquired resistance. J Agric Food Chem 57:4279–4286. https://doi.org/10.1021/jf8031364

    Article  PubMed  CAS  Google Scholar 

  12. De Oliveira CS, Lira BF, Barbosa-Filho JM, Lorenzo JGF, de Athayde-Filho PF (2012) Synthetic approaches and pharmacological activity of 1, 3, 4-oxadiazoles: a review of the literature from 2000–2012. Molecules 17:10192–10231. https://doi.org/10.3390/molecules170910192

    Article  PubMed  CAS  Google Scholar 

  13. Mullican MD, Wilson MW, Conner DT, Kostlan CR, Schrier DJ, Dyer RD (1993) Design of 5-(3, 5-di-tert-butyl-4-hydroxyphenyl)-1, 3, 4-thiadiazoles,-1, 3, 4-oxadiazoles, and-1, 2, 4-triazoles as orally active, nonulcerogenic antiinflammatory agents. J Med Chem 36:1090–1099. https://doi.org/10.1021/jm00060a017

    Article  PubMed  CAS  Google Scholar 

  14. Manjunatha K, Poojary B, Lobo PL, Fernandes J, Kumari NS (2010) Synthesis and biological evaluation of some 1, 3, 4-oxadiazole derivatives. Eur J Med Chem 45:5225–5233. https://doi.org/10.1016/j.ejmech.2010.08.039

    Article  PubMed  CAS  Google Scholar 

  15. Karthikeyan MS, Prasad DJ, Mahalinga M, Holla BS, Kumari NS (2008) Antimicrobial studies of 2, 4-dichloro-5-fluorophenyl containing oxadiazoles. Eur J Med Chem 43:25–31. https://doi.org/10.1016/j.ejmech.2007.03.013

    Article  PubMed  CAS  Google Scholar 

  16. Singh DV, Mishra AR, Mishra RM (2005) Synthesis and antifungal activity of new 1, 3, 4-oxadiazolo [3, 2-b]-s-triazine-5-ones and their thiones analogues. Ind J Heterol Chem 14:289–292

    CAS  Google Scholar 

  17. Suresh DB, Jamatsing DR, Pravin SK, Ratnamala SB (2016) Synthesis, characterization and antioxidant activity of carvacrol containing novel thiadiazole and oxadiazole moieties. Mod Chem Appl 4:193. https://doi.org/10.4172/2329-6798.1000193

    Article  CAS  Google Scholar 

  18. Franski R (2005) Biological activities of the compounds bearing 1, 3, 4-oxa (thia) diazole ring. Asia J Chem 17:2063

    CAS  Google Scholar 

  19. Rajput JD, Bagul SD, Pete UD, Zade CM, Padhye SB, and Bendre RS (2017) Perspectives on medicinal properties of natural phenolic monoterpenoids and their hybrids. Mol Divers. https://doi.org/10.1007/s11030-017-9787-y

  20. Rajput JD, Bagul SD, Tadavi SK, Karandikar PS, Bendre RS (2016) Design, synthesis, and biological evaluation of novel class diindolyl methanes (DIMs) derived from naturally occurring phenolic monoterpenoids. Med Chem. https://doi.org/10.4172/2161-0444.1000336

  21. Bagul SD, Rajput JD, Tadavi SK, Bendre RS (2016) Design synthesis and biological activities of novel 5-isopropyl-2-methylphenolhydrazide-based sulfonamide derivatives. Res Chem Int. https://doi.org/10.1007/s11164-016-2759-5

  22. Rajput JD, Bagul SD, Bendre RS (2016) Design, synthesis, biological screenings and docking simulations of novel carvacrol and thymol derivatives containing acetohydrazone linkage. Research on Chemical Intermediates. Res Chem Intermed 43:4893–4906. https://doi.org/10.1007/s11164-017-2919-2

    Article  CAS  Google Scholar 

  23. Srivastava C, Reddy DS (2006) Evaluation of antifeedant activity of neem formulations against tobacco caterpillar Spodoptera litura. Indian J Plant Prot 34:126

    Google Scholar 

  24. Akhtar Y, Isman MB (2004) Comparative growth inhibitory and antifeedant effects of plant extracts and pure allelochemicals on four phytophagous insect species. J Appl Ento 128:32–38. https://doi.org/10.1046/j.1439-0418.2003.00806.x

    Article  CAS  Google Scholar 

  25. Singh RP, Pant NC (1980) Lycorine—a resistance factor in the plants of subfamily Amaryllidoideae (Amaryllidaceae) against desert locust, Schistocerca gregaria F. Cell Mol Life Sci 36:552–553

    Article  CAS  Google Scholar 

  26. Shakil NA, Pandey A, Singh MK, Kumar J, Awasthi SK, Pankaj, Shrivastava C, Singh MK, Pandey RP (2010) Synthesis and bioefficacy evaluation of new 3-substituted-3,4-dihydro-1,3-benzoxazines. J Environ Sci Health Part B 45:108

  27. Isman Koul BO, Lucyzynski A, kaminanki J (1995) Insecticidal and antifeedant bioactivities of neem oils and their relationship to Azadirachtin content. J Agric Food Chem 38:1407–1411. https://doi.org/10.1021/jf00096a024

    Article  Google Scholar 

  28. Vashi BS, Shah VH (1996) Synthesis and biological screening of substituted thymolylthiazolidinones and thymolylazetidinones. J Indian Chem Soc 73:491–492

    CAS  Google Scholar 

  29. Vashi BS, Mehta DS, Shah VH (1996) Synthesis of 2, 5-disubstituted -1, 3, 4-oxadiazole, 1, 5-disubstituted-2-mercapto-1, 3, 4-triazole and 2, 5-disubstituted-1, 3, 4-thiadiazole derivatives as potential antimicrobial agents. Indian J Chem Sect B Organ Chem 35:111–115

    Google Scholar 

  30. Yanagi M, Sugizaki H, Toya T, Kato Y, Shirakura H, Watanabe T, Yajima Y, Kodama S, Masui A, Yanai T, Tsukamoto Y, Sawada Y, Yokoi S (1992) Preparation of hydrazine derivatives and their pesticidal activity. Chem Abstr 117:212514

    Google Scholar 

  31. Chapleo CB, Myers M, Myers PL, Saville JF, Smith AC, Stillings MR, Tulloch IF, Walter DS, Welbourn AP (1986) Substituted 1, 3, 4-thiadiazoles with anticonvulsant activity. 1. Hydrazines. J Med Chem 29:2273–2280. https://doi.org/10.1021/jm00161a024

    Article  PubMed  CAS  Google Scholar 

  32. Shailaja M, Anitha M, Manjula A, Vittal Rao B (2010) Synthesis and biological activity of novel 2, 5 disubstituted-1, 3, 4-oxadiazoles. Indian J Chem Sect Chem B Organ 49:1088

    Google Scholar 

  33. Tully WR, Gardner CR, Gillespie RJ, Westwood R (1991) 2-(oxadiazolyl)-and 2-(thiazolyl) imidazo [1, 2-a] pyrimidines as agonists and inverse agonists at benzodiazepine receptors. J Med Chem 34:2060–2067. https://doi.org/10.1021/jm00111a021

    Article  PubMed  CAS  Google Scholar 

Download references

Acknowledgements

Authors are thankful to CSIR, New Delhi, India, for financial assistance under the major research project [F. No. 02 (0130)/13/EMR-II].

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Ratnamala S. Bendre.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (docx 1473 KB)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Bagul, S.D., Rajput, J.D., Srivastava, C. et al. Insect growth regulatory activity of carvacrol-based 1,3,4-thiadiazoles and 1,3,4-oxadiazoles. Mol Divers 22, 647–655 (2018). https://doi.org/10.1007/s11030-018-9823-6

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11030-018-9823-6

Keywords

Navigation