Abstract
Research results are summarized from a series of insect juvenile hormone analogs derived from 2-(4-hydroxybenzyl)-1-cycloalkanones, which have been investigated at the Institute of Organic Chemistry and Biochemistry in Prague during the past 20 years. At present, practical application of several prospective structures for insect control is under investigation. Biological activity values were determined to delineate the most important subseries of compounds and the most promising insect juvenile hormone analogs selected from the subseries. Carbamates, and in particular compound 47 proved to be highly active against aphids, cockroaches, flies, and many other insect species.
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REFERENCES
ANDERSON, J. R., HENRICK, C. A., SIDALL, J. B., and ZURFLÜH, R. 1972. Stereoselective synthesis of the racemic C-17 juvenile hormone of Cecropia. J. Am. Chem. Soc. 94:5379–5386.
ELBERT, T., ČERNÝ, B., WIMMER, Z., and SERGENT, L. 1993. Regio-and stereoselective tritiation of the juvenoid analog W-328. Collect. Czech. Chem. Commun. 58:1164–1168.
ELBERT, T., HAVLÍČEK, L., WIMMER, Z., and BUBNER, M. 1994. Synthesis of the 14C-labelled juvenoid W-328. J. Labell. Comp. Radiopharm. 34:377–382.
ELBERT, T., REJZEK, M., and VIRELIZIER, H. 1996. Regioselective tritiation of carbamate dicyclic juvenoids. Collect. Czech. Chem. Commun. 61:946–950.
FICHERA, L., ESTEVA, M., WIMMER, Z., RODRIGUEZ, J. B., and GROS, E. G. 1995. Effects of juvenile hormone analogues (JHA) on the development of Trpanosoma cruzi. Z. Naturforsch. 50c:578–580.
HENRICK, C. A. 1995. Juvenoids, pp. 147–213, in C. R. A. Godfrey (ed.), Agrochemicals from Natural Products. Marcel Dekker, New York.
HENRICK, C. A., SCHAUB, F., and SIDDALL, J. B. 1972. Stereoselective synthesis of the C-18 Cecropia juvenile hormone. J. Am. Chem. Soc. 94:5371–5378.
HRDÝ, I. 1974. Effects of juvenoids on insecticide-susceptible and resistant aphids (Myzus persicae, Aphis fabae and Therioaphis maculata; Homoptera, Aphididae). Acta Entomol. Bohemoslov. 71:367–381.
HRDÝ, I. 1985. The role of juvenile hormones and juvenoids in soldier formation in Rhinotermitidae, pp. 245–249, in J. A. L. Watson, B. M. Okot-Kotber, and C. Noirot (eds.), Caste Differentiation in Social Insects. Pergamon Press, London.
HRDÝ, I., and KULDOVÁ, J. 1981. A standardized spray-residue method for measuring, and a dip test for monitoring resistance in aphids, pp. 21–28, in International Organization for Biological Control, West Palaearctic Regional Section Bull IV/3.
KARRER, F. E., SCHEURER, R., and HERZOG, A. 1974. New Insect Growth Regulators. The Third International Congress on Pesticide Chemistry, Helsinki, Abstract No. 378.
KODRÍK, D. 1991. Effect of a novel juvenoid on the German cockroach, pp. 467–470, in I. Hrdý (ed.). Insect Chemical Ecology. Academia, Prague; and SPB Academic Publishers, The Hague.
KONTEV, C. A., HANZAL, R., KOZÁK, L., SEHNAL, F., and WIMMER, Z. 1991. Juvenoids highly active on Pentatomid bug, Eurygaster intergriceps, pp. 471–474, in Hrdý (ed.). Insect Chemical Ecology. Academia, Prague, and SPB Academic Publishers, The Hague.
KULDOVÁ, J., HRDÝ, I., WIMMER, Z., ROMAŇUK, M., and SEHNAL, F. 1990. Biological activities of juvenoids derived from 2-(4-hydroxybenzyl)-1-cyclohexanone. Acta Entomol. Bohemoslov. 87:332–335.
KULDOVÁ, J., WIMMER, Z., and HRDÝ, I. 1991. Biological activity of juvenoids derived from 2-(4-hydroxybenzyl)-1-cyclohexanone on some homopteran pests, pp. 461–466, in I. Hrdý (ed.), Insect Chemical Ecology. Academia, Prague; and SPB Academic Publishers, The Hague.
KULDOVÁ, J., HRDÝ, I., and WIMMER, Z. 1994. Selection of compounds acting as aphid development and reproduction regulators: Laboratory screening. Pestic. Sci. 41:319–325.
KULDOVÁ, J., HRDÝ, I., and WIMMER, Z. 1997. Response of the hop aphid, Phorodon humuli, to the application of juvenile hormone analogue in the field trials. J. Appl. Entomol. (Submitted).
NOVÁK, K., ZELENÝ, J., and SEHNAL, F. 1991. Activities of a new juvenoid on the representatives of Homoptera, pp. 457–460, in I. Hrdý (ed.). Insect Chemical Ecology. Academia, Prague; and SPB Academic Publishers, The Hague.
PENER, M. P., AYALI, A., KELMER, G., BENNETTOVÁ B., NĚMEC, V., REJZEK, M., and WIMMER, Z. 1997. Comparative testing of several juvenile hormone analogues in two species of locusts, Locusta migratoria migratorioides and Schistocerca gregaria. Arch. Insect Biochem. (In press).
REJZEK, M., WIMMER Z., ROMAŇUK, M., and HRDÝ, I. 1991. Synthesis and practical application of juvenoids, pp. 481–484, in I. Hrdý (ed.). Insect Chemical Ecology. Academia, Prague; and SPB Academic Publishers, The Hague.
REJZEK, M., ZAREVÚCKA, M., and WIMMER, Z. 1992. Carbamate series of juvenoids. BioMed. Chem. Lett. 2:963–966.
REJZEK, M., WIMMER, Z., ŠAMAN, D., ŘÍČÁNKOVÁ, M., NĚMEC, V. 1994a. Synthesis and structure-activity relationships of juvenoids derived from 2-(4-hydroxybenzyl)-l-cycloalkanones. Helv. Chim. Acta 77:1241–1255.
REJZEK, M., WIMMER, Z., ZAREVÚCKA, M., ŠAMAN, D., PAVLÍK, M., and ŘÍČÁNKOVA, M. 1994b. Chiral juvenoids derived from 2-substituted cyclohexanols. Tetrahedron Asymm. 5:1501–1512.
ROMAÑUK, M. 1976. Bioanalogues of the insect juvenile hormone. Nova Acta Leopold. Suppl. 7:445–454.
SLÁMA, K., and ROMAŇUK, M. 1976. Juvenogens, biochemically activated juvenoid complexes. Insect Biochem. 6:579–586.
SLÁMA, K., ROMAŇUK, M., ŠORM, F. 1974. Insect hormones and bioanalogues. Springer-Verlag, Vienna, Austria.
SLÁMA, K., WIMMER, Z., and ROMAŇUK, M. 1977. Juvenile hormone activity of some glycosidic juvenogens. Hoppe-Seyler's Z. Physiol. Chem. 359:1407–1412.
SU, N.-Y., and SCHEFFRAHN, R. H. 1990. Potential of insect growth regulators as termicides: A review. Sociobiology 17:313–328.
TYKVA, R., BENNETTOVÁ, B., REJZEK, M., WIMMER, Z., LANDA, V., and ZAREVÚCKA, M. 1997. A study of juvenile hormone bioanalogs derived from 2-(4-hydroxybenzyl)-6-methyl-l-cyclohexanone. Arch. Insect Biochem. (In press).
VINUELA, E., ONDRÁČEK, J., JACAS, J., ADÁN, A., REJZEK, M., and WIMMER, Z. 1994. Laboratory evaluation of five new JHA derivatives from 2-(4-hydroxybenzyl)-l-cyclohexanone against Tribolium castaneum (Herbst). J. Stored Prod. Res. 30:149–155.
WIMMER, Z., and ROMAŇUK, M. 1981. The syntheses of biologically active 2-(4-hydroxybenzyl)-l-cyclohexanone derivatives. Collect. Czech. Chem. Commun. 46:2573–2586.
WIMMER, Z., and ROMAŇUK, M. 1982. The synthesis of juvenogen derivative of 2-[4-(3-ethoxy-3-methyl-1-butoxy)benzyl]-1-cyclohexanol. Collect. Czech. Chem. Commun. 47:1878–1883.
WIMMER, Z., and ROMAŇUK, M. 1989. Oxime ethers as potential juvenoids: The role of the optical isomerism. 13th Conference on Isoprenoids, Abstract of Papers, p. 14.
WIMMER, Z., STREINZ, L., and ROMAÑUK, M. 1985. Preparation of carbamate derivatives of 2-(4-hydroxybenzyl)-l-cyclohexanone with a juvenoid activity. Collect. Czech. Chem. Commun. 50:2453–2456.
WIMMER, Z., ROMAŇUK, M., and SLÁMA, K. 1988a. Synthesis and application of juvenile hormone analogues, pp. 737–736, in F. Sehnal, A. Zabza, and D. L. Denlinger (eds.). Endocrinological Frontiers in Physiological Insect Ecology. Wroclaw, Poland.
WIMMER, Z., ŠAMAN, D., SMOLÍKOVÁ, J., and ROMAŇUK, M. 1988b. Oxime ethers as potential juvenoids. Liebigs Ann. Chem. 1988:1091–1094.
WIMMER, Z., VAŠÍČKOVÁ, S., ŠAMAN, D., and ROMAŇUK, M. 1990. Oxime ethers as potential juvenoids: Synthesis of optical isomers. Liebigs Ann. Chem. 1990:847–852.
WIMMER, Z., ROMAŇUK, M., KULDOVÁ, J., HRDÝ, I., and SEHNAL, F. 1991a. JH activity of selected insect juvenile hormone analogs, pp. 453–456, in I. Hrdý (ed.). Insect Chemical Ecology. Academia, Prague; and SPB Academic Publishers. The Hague.
WIMMER, Z., ROMAŇUK, M., and RUPEŠ, V. 1991b. Controlled release formulation of juvenoids, pp. 489–492, in I. Hrdý (ed.). Insect Chemical Ecology. Academia, Prague; and SPB Academic Publishers, The Hague.
WIMMER, Z., ŠAMAN, D., and FRANCKE, W. 1994a. Novel juvenoids of the 2-(4-hydroxybenzyl)-1-cyclohexanone series. Helv. Chim. Acta 77:502–508.
WIMMER, Z., ŠAMAN, D., NĚMEC, V., and FRANCKE, W. 1994b. Carbamate series of juvenoids: Variation in O-alkyl substitution. Helv. Chim. Acta 77:561–568.
ZEMAN, P., KYSELOVÁ, M., RUPEŠ, V., WIMMER, Z., and VRBA, Z. 1992. Management of a German cockroach population with a juvenoid bait formulation: An experiment in residential buildings. Entomol. Exp. Appl. 62:47–53.
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Wimmer, Z., Rejzek, M., Zarevúcka, M. et al. A Series of Bicyclic Insect Juvenile Hormone Analogs of Czech Origin: Twenty Years of Development. J Chem Ecol 23, 605–628 (1997). https://doi.org/10.1023/B:JOEC.0000006399.07779.16
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DOI: https://doi.org/10.1023/B:JOEC.0000006399.07779.16
- Insect juvenile hormone analogs
- 2-(4-hydroxybenzyl)-1-cycloalkanones
- Tenebrio molitor
- Coleoptera
- Tenebrionidae
- Dysdercus cingulatus
- Pyrrhocoris apterus
- Heteroptera
- Pyrrhocoridae
- Acyrthosiphon pisum
- Phorodon humuli
- Homoptera
- Aphididae
- Locusta migratoria migratortorioides
- Orthoptera
- Acrididae
- Reticulitermes lucifugus
- Prorhinotermes simplex
- Isoptera
- Rhinotermitidae
- Blattella germanica
- Blattodea
- Blattidae
- Musca domestica
- Diptera
- Muscidae
- Daphnia magna Cladocera
- Daphnidae
- Trypanosoma cruzi
- Euglenozoa
- Trypanosomatidae