Pyrrole Insecticides: A New Class of Agriculturally Important Insecticides Functioning as Uncouplers of Oxidative Phosphorylation

  • D. A. Hunt
  • M. F. Treacy
Chapter
Part of the Applied Agriculture book series (APPLAGRIC)

Abstract

In the never-ending search for new insecticides and insecticidal leads, researchers have consistently relied upon nature for guidance (Addor 1995; Henrick 1995). This strategy in general has provided the research community with a plethora of compound classes possessing biological activity, with fermentation chemistry serving as one of the foremost sources for compounds derived from nature. Fermentation technology has proven invaluable for the generation of many classes of compounds encompassing broad ranges of biological activities amendable for exploitation by both the pharmaceutical and agrochemical industries.

Keywords

Fermentation Respiration Hunt Pyrazole Carbamate 

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References

  1. Addor RW (1995) Insecticides. In: Godfrey CRA (ed) Agrochemicals from natural products. arcel Dekker New York, pp 1–62Google Scholar
  2. Addor RW, Babcock TJ, Black BC, Brown DG, Diehl RE, Jurch JA, Kameswaran V, Kamhi VM, Kremer KA, Kuhn, DG, Lovell JB, Lowen GT, Miller TP, Peevey RM, Siddens JK, Treacy MF, Trotto SH, Wright DP Jr (1992) Insecticidal pyrroles. Discovery and overview. In: Baker DR, Fenyes JG, Steffens JJ (eds) Synthesis and chemistry of agrochemicals III, no 504. American Chemical Society, Washington, DC, pp 283–297CrossRefGoogle Scholar
  3. Anonymous (1992) AC 303,630 experimental insecticide-miticide. Technical bulletin. American Cyanamid Company, Princeton, New Jersey, pp 1–11Google Scholar
  4. Benages IA, Albonico SM (1978) 2-Chloroacrylonitrile as a cyclodipolarophile in 1,3- cycloadditions. 3-Cyanopyrroles. J Org Chem 43: 4273–4276CrossRefGoogle Scholar
  5. 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: 115–128CrossRefGoogle Scholar
  6. Campanhola C, Plapp FW Jr. (1989) Toxicity and synergism of insecticides against susceptible and pyrethroid-resistant third-instars of the tobacco budworm (Lepidoptera: Noctuidae). J Econ Entornai 82: 1495–1501Google Scholar
  7. Carter G, Nietsche J, Goodman J, Tory M, Dunne T, Borders D, Testa R (1987) LL-F42248α, a novel chlorinated pyrrole antibiotic. J Antibiot 40: 233–236PubMedCrossRefGoogle Scholar
  8. Corbett JR, Wright K, Baillie AC (1984) Pesticides interfering with respiration. In: The biochemical mode of action of pesticides, 2nd edn. Academic Press, London, pp 1–49Google Scholar
  9. Farlow RA, Treacy MF, Miller TP, Burkhart SE, Gard IE (1991) Efficacy of AC 303,630 against insect pests on cotton. In: Herber DJ (ed) Proc Beltwide Cotton Conf, National Cotton Council, Memphis, Tennessee, pp 741–744Google Scholar
  10. Filler R, Kobayashi Y (1986) Biomedical aspects of fluorine chemistry. Elsevier Biomedical Press, New YorkGoogle Scholar
  11. Gange DM, Donovan S, Lopata RJ, Henegar K (1995) The QSAR of insecticidal uncouplers. In: Hansch C, Fujita T (eds) Classical and three-dimensional QSAR in agrochemistry, no 606. American Chemical Society, Washington, DC, pp 199–212CrossRefGoogle Scholar
  12. Hansch C, Kiehs K, Lawrence G (1965) The role of substituents in the hydrophobic bonding of phenols by serum and mitochondrial proteins. J Am Chem Soc 87: 5770–5773PubMedCrossRefGoogle Scholar
  13. Henrick CA (1995) Pyrethroids. In: Godfrey CRA (ed) Agrochemicals from natural products. Marcel Dekker, New York, pp 63–146Google Scholar
  14. Hung CF, Kao CH, Liu CC, Lin JG, Sun CN (1990) Detoxifying enzymes of selected insect species with chewing and sucking habits. J Econ Entomol 83: 361–365Google Scholar
  15. Hunt DA (1994) 2-Arylpyrroles: novel uncouplers of oxidative phosphorylation. In: Briggs G (ed) Advances in the chemistry, Cambridge, pp 127–140Google Scholar
  16. Kuhn DG, Addor RW, Diehl RE, Furch JA, Kamhi VM, Henegar KE, Kremer KA, Lowen GT, Black BC, Miller TP, Treacy MF (1993) Insecticidal pyrroles. In: Duke SO, Menn JJ, Plimmer JR (eds) Pest control with enhanced environmental safety, no 524. American Chemical Society, Washington, DC, pp 219–232CrossRefGoogle Scholar
  17. Labbe-Bois R, Larvelle C, Godfroid J (1975) Quantitative structure-activity relationships for dicoumarol antivitamins K in the upcoupling of mitochondrial oxidative phosphorylation. J Med Chem 18: 85–90CrossRefGoogle Scholar
  18. Loomis WF, Lipmann F (1948) Reversible inhibition of the coupling between phosphorylation and oxidation. J Biol Chem 173: 807–808PubMedGoogle Scholar
  19. Miller TP, Treacy MF, Gard IE, Lovell JB, Wright DP, Addor RW, Kamhi VM (1990) AC 303,630: summary of 1988–1989 field trial results. In: Proc Brighton Crop Prot Conf— Pests and Diseases, British Crop Protection Council, Brighton, SussexGoogle Scholar
  20. Mitchell P (1961) Coupling of phosphorylation to electron and hydrogen transfer by a chemiosmotic type of mechanism. Nature 191: 144PubMedCrossRefGoogle Scholar
  21. Muehleisen DP (1987) Induction and regulation of detoxification enymes in Heliothis zea by allelochemicals and insecticides. PhD Diss, Texas A & M University, College Station, 127 ppGoogle Scholar
  22. Pimprale SS, Besco CL, Bryson PK, Brown TM (1997) Increased susceptibility of pyrethroid-resistant tobacco budworm (Lepidoptera: Noctuidae) to chlorfenopyr. J Econ Entomol 90: 49–54Google Scholar
  23. Tollenarere J (1973) Structure-activity relationships of three groups of uncouplers of oxidative phosphorylation: salicylanilide 2-trifluoromethylbenzimidazoles and phenols. J Med Chem 16: 791–796CrossRefGoogle Scholar
  24. Treacy M, Miller T, Black B, Gard I, Hunt D, Hollingworth RM (1994) Uncoupling activity and pesticidal properties of pyrroles. Biochem Soc Trans 22: 244–247PubMedGoogle Scholar
  25. Treacy MF, Miller TP, Gard IE, Lovell JB, Wright DP (1991) Characterization of insecticidal properties of AC 303,630 against tobacco budworm (Heliothis virescens) larvae. In: Herber DJ (ed) Proc Beltwide Cotton Conf National Cotton Council, Memphis, Tennessee, pp 738–741Google Scholar
  26. Wilkinson CF (1983) Role of mixed-function oxidases in insecticide resistance. In: Georghiou GP, Sarto T (eds) Pest resistance to pesticides. Plenum, New York, pp 175–206CrossRefGoogle Scholar
  27. Yu S (1983) Age variation in insecticide susceptibility and detoxification capacity of fall armyworm (Lepidoptera: Noctuidae) larvae. J Econ Entomol 76: 219–222Google Scholar

Copyright information

© Springer-Verlag Berlin Heidelberg 1998

Authors and Affiliations

  • D. A. Hunt
    • 1
  • M. F. Treacy
    • 1
  1. 1.Agricultural Products Research DivisionAmerican Cyanamid CompanyPrincetonUSA

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