Advertisement

Experientia

, Volume 45, Issue 6, pp 580–583 | Cite as

Arylpyridyl-thiosemicarbazones: A new class of anti-juvenile hormones active against Lepidoptera

  • A. E. Barton
  • K. D. Wing
  • D. P. Le
  • R. A. Slawecki
  • R. Feyereisen
Research Articles

Summary

A new class of anti-juvenile hormone agents is described. Active anti-juvenile hormone compounds were either diazine thiosemicarbazones or aryl substituted pyridyl thiosemicarbazones, synthesized from substituted benzaldehydes. While many analogs in these classes showed feeding and growth inhibition in a variety of insects, a select group caused formation of precocious pupal characteristics inAgrotis ipsilon (black cutworm) andHeliothis virescens (tobacco budworm) and black cuticle and precocious pupae inManduca sexta (tobacco hornworm). They were active only by diet incorporation. The symptoms of precocious development could be reversed by co-administration of a juvenoid. One of the active compounds was shown to inhibit juvenile hormone biosynthesis in vitro by corpora allata of the cockroachDiploptera punctata. However, none of the compounds were active inhibitors of purified chicken liver prenyl transferase.

Key words

Thiosemicarbazones anti-juvenile hormone insect growth regulator Lepidoptera juvenile hormone biosynthesis inhibitor 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    Retnakaran, A., Granett, J., and Ennis, T., Comp. Insect Physiol.12 (1985) 529; Ishaaya, I., Nemny, N. E., and Ascher, K. R. S., Phytoparasitica12 (1984) 193.Google Scholar
  2. 2.
    Staal, G. B., et al., in: Bioregulators for Pest Control, p. 201. ACS Sympos. series 276 (1985).Google Scholar
  3. 3.
    Staal, G. B., A. Rev. Ent.31 (1986) 391.Google Scholar
  4. 4.
    deMilo, A. B., Redfern, R. E., and Borkovec, A. B., J. Agric. Food Chem.31 (1983) 713.Google Scholar
  5. 5.
    Chen, C.-T., Chen, S.-F., and Lee, S.-J., Heterocycles5 (1976) 239.Google Scholar
  6. 6.
    Barton, A. E., and Le, D. P., Synthetic Commun., submitted for publication.Google Scholar
  7. 7.
    Fischer, U., Schneider, F. and Zurfluh, R., Chem. Abstr.92 (1980) 643. (58473X) Eur. Pat. Specn. 4334F. Hoffmann-La Roche.Google Scholar
  8. 8.
    Feyereisen, R., Meth. Enzym.111 (1985) 530.Google Scholar
  9. 9.
    Rilling, H. C., Meth. Enzym.110 (1984) 145.Google Scholar
  10. 10.
    Jones, D., Jones, G., and Bhaskaran, G., Ent. exp. appl.28 (1980) 259.Google Scholar
  11. 11.
    Safranek, L., and Riddiford, L. M., J. Insect. Physiol.21 (1975) 1931.Google Scholar
  12. 12.
    Brooks, G. T., Pratt, G. E., Mace, D. W., and Cocks, J. A., Pest. Sci.16 (1985) 132.Google Scholar
  13. 13.
    Quistad, G., Cerf, D. C., Kramer, S. J., Bergot, B. J. and Schooley, D. A., J. Agric. Food Chem.33 (1985) 47.Google Scholar
  14. 14.
    Sartorelli, A. C., Adv. Enzym. Reg.15 (1976) 117.Google Scholar
  15. 15.
    Klayman, D. L., Bartosevich, J. F., Griffin, T. S., Mason, C. J., and Scovill, J. P., J. med. Chem.22 (1979) 855.PubMedGoogle Scholar
  16. 16.
    Pedersen, L. E. K., Svendsen, A., and Per, D., Klemmensen Pest. Sci.25 (1984) 462.Google Scholar

Copyright information

© Birkhäuser Verlag Basel 1989

Authors and Affiliations

  • A. E. Barton
    • 1
  • K. D. Wing
    • 1
  • D. P. Le
    • 1
  • R. A. Slawecki
    • 1
  • R. Feyereisen
    • 2
  1. 1.Research LabsRohm and Haas Co.Spring HouseUSA
  2. 2.Dept of Entomology and Agricultural ChemistryOregon State UniversityCorvallisUSA

Personalised recommendations