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NEW INSECTICIDES WITH ECDYSTEROIDAL AND JUVENILE HORMONE ACTIVITY
Abstract
Agrochemical research over the last two decades has resulted in the discovery of chemically novel insecticides that mimic the action of the two insect growth and developmental hormones, the steroidal 20-hydroxyecdysone (20E) and the sesquiterpenoid juvenile hormone (JH). Bisacylhydrazines are non-steroidal agonists of 20E and exhibit their insecticidal activity via interaction with the ecdysteroid receptor proteins. Interestingly, two of the bisacylhydrazine (tebufenozide and RH-2485) insecticides are very selectively toxic to lepidopteran pests. These insecticides are safe to beneficial insects and have a benign ecotoxicological profile. Aromatic non-terpenoidal insecticides (fenoxycarb and pyriproxyfen) mimic the action of JHs. However, like the JHs, their exact mode of action is not well understood. These insecticides are toxic to a broad spectrum of insects during their embryonic, last larval, or reproductive stages. The insecticidal, ecotoxicological properties and the mode of action of the two groups of insecticides are reviewed in this article.
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“One alternative strategy that has been successfully commercially developed is the use of non-steroidal ecdysteroid analogues as insecticidal compounds (bisacylhydrazines; [90]) since these chemicals are easy to synthesise, non-polar and resistant to metabolism.”
From Ecdysteroids (2021) · cites this paper as [90]
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“Over the past four decades, insecticidal JH analogs (JHAs), such as methoprene, have appeared (Staal, 1975; Dhadialla et al., 1998) and shown to be effective against certain insects, including D.”
BackgroundIsaacs, R., Mason, K. S., & Maxwell, E. M. (2005) · Journal of Economic Entomology · doi:10.1093/jee/98.2.415 · Cited by 21
“…ecdysis when ingested by larval stages of Lepidoptera (Dhadialla et al. 1998; Smagghe et al. 1999), and ovicidal activity against some Lepidoptera has been reported (Biddinger et al. 1998, Dhadialla et al. 1998, Trisyono and Chippendale 1998, Pons et al. 1999, Knight 2000, Carlson et al. 2001).”
BackgroundSelection and Life History Traits of Tebufenozide-Resistant Sugarcane Borer (Lepidoptera: Crambidae)
Akbar, W., Ottea, J. A., Beuzelin, J. M., Reagan, T. E., & Huang, F. (2008) · Journal of Economic Entomology · doi:10.1603/0022-0493-101.6.1903 · Cited by 21
“With this insect-speciÞc target site, tebufenozide poses little or no apparent threat to nontarget organisms (Rohm and Haas 1994, Smagghe and Degheele 1995, Dhadialla et al. 1998).”
BackgroundBakr, R., El-Aziz, M. F. A., El-Barky, N. M., Awad, M. A., & El-Halim, H. A. (2013) · Egyptian Academic Journal of Biological Sciences. C, Physiology and Molecular Biology/Egyptian Academic Journal of Biological Sciences. C, Physiology and Molecular Biology · doi:10.21608/eajbsc.2013.16092 · Cited by 21
Steered molecular dynamics for studying ligand unbinding of ecdysone receptor
Hu, X., Hu, S., Wang, J., Dong, Y., Zhang, L., & Dong, Y. (2017) · Journal of Biomolecular Structure and Dynamics · doi:10.1080/07391102.2017.1401002 · Cited by 21
Activation of neuroblast proliferation in explant culture of the Drosophila larval CNS
Datta, S. (1999) · Brain Research · doi:10.1016/s0006-8993(98)01292-x · Cited by 21
Carton, B., Smagghe, G. J., & Tirry, L. (2003) · Journal of Applied Entomology · doi:10.1046/j.1439-0418.2003.00734.x · Cited by 21
“When tested against Lepidoptera and Coleoptera, a clear difference is noted between the toxicity of methoxyfenozide and halofenozide (Le et al., 1996; Farinòs et al., 1999; Carton et al., 2000).”
BackgroundInfluentialMosallanejad, H., Soin, T., Swevers, L., Iatrou, K., Nakagawa, Y., & Smagghe, G. J. (2008) · Pesticide Biochemistry and Physiology · doi:10.1016/j.pestbp.2008.06.004 · Cited by 21
Reay‐Jones, F. P. F., Akbar, W., McAllister, C. D., Reagan, T. E., & Ottea, J. A. (2005) · Journal of Economic Entomology · doi:10.1603/0022-0493-98.3.955 · Cited by 21
Manipulation of gene expression by an ecdysone-inducible gene switch in tumor xenografts
Karns, L. R., Kisielewski, A. E., Gulding, K. M., & Theodorescu, D. (2001) · BMC Biotechnology · doi:10.1186/1472-6750-1-11 · Cited by 21
“[ 11 ] The 96 well plates were visualized under a fluorescent microscope before and after addition of the compound.”
Araújo, R. D. S., Bernardes, R. C., Fernandes, K. M., Lima, M. A. P., Martins, G. F., & Tavares, M. G. (2019) · Environmental Pollution · doi:10.1016/j.envpol.2019.06.087 · Cited by 20
Browning, C., McEwen, A. G., Mori, K., Yokoi, T., Moras, D., Nakagawa, Y., & Billas, I. M. L. (2021) · Journal of Pesticide Science · doi:10.1584/jpestics.d20-095 · Cited by 20
Swevers, L., Soin, T., Mosallanejad, H., Iatrou, K., & Smagghe, G. J. (2008) · Insect Biochemistry and Molecular Biology · doi:10.1016/j.ibmb.2008.06.001 · Cited by 20
“Dibenzoylhydrazine-type non-steroidal ecdysone agonists such as methoxyfenozide (RH-2485), tebufenozide (RH-5992), halofenozide (RH-0345) and chromafenozide (ANS-118) are narrow-spectrum insect growth regulators (IGRs) that act through the induction of a precocious and lethal larval molting process in susceptible inse…”
BackgroundInfluentialQSAR for Binding Affinity of Substituted Dibenzoylhydrazines to Intact Sf-9 Cells
Ogura, T., Nakagawa, Y., Minakuchi, C., & Miyagawa, H. (2005) · Journal of Pesticide Science · doi:10.1584/jpestics.30.1 · Cited by 20
Hamaidia, K., Tine‐Djebbar, F., & Soltani, N. (2018) · Physiological Entomology · doi:10.1111/phen.12261 · Cited by 20
“Thus, dibenzoylhydrazine compounds can be applied successfully as environmentally safe insecticides against lepidopteran and coleopteran insect species (Dhadialla et al., 1998; Pineda et al., 2004; Dhadialla et al., 2005; Dhadialla & Ross, 2007; Smagghe et al., 2012; Dallaire & Cusson, 2017).”
BackgroundZhang, J., Liu, X., Liu, Y., An, Y., Fang, H., Michaud, J. P., Zhang, H., Li, Y., Zhang, Q., & Li, Z. (2019) · Journal of Economic Entomology · doi:10.1093/jee/toz155 · Cited by 21
Peck, D. C., Olmstead, D. L., & Morales-Rodríguez, A. (2008) · Pest Management Science · doi:10.1002/ps.1592 · Cited by 20
Amrani, L., Zerguine, K., Farine, J., Smagghe, G. J., & Soltani-Mazouni, N. (2004) · Pesticide Biochemistry and Physiology · doi:10.1016/j.pestbp.2004.07.004 · Cited by 20
“Due to secondary effects of conventional insecticides on the environment, the class of selective insect growth regulators (IGRs) have shown promise in controlling insects of agricultural, medical, and veterinary importance [6].”
BackgroundNakagawa, Y., Smagghe, G. J., Tirry, L., & Fujita, T. (2001) · Pest Management Science · doi:10.1002/ps.429 · Cited by 20
Sun, X., Song, Q., & Barrett, B. A. (2003) · Insect Biochemistry and Molecular Biology · doi:10.1016/s0965-1748(03)00082-1 · Cited by 20
Špirhanzlová, P., Groef, B. D., Nicholson, F. E., Grommen, S. V. H., Marras, G., Sébillot, A., DEMENEIX, B. A., Pallud, S. E., Lemkine, G. F., Tindall, A. J., et al. (2017) · Comparative Biochemistry and Physiology Part C Toxicology & Pharmacology · doi:10.1016/j.cbpc.2017.06.006 · Cited by 20
An investigation on some toxic effects of pyriproxyfen in adult male mice.
Shahid, A., Zaidi, S. D. E. S., Akbar, H., & Saeed, S. (2019) · PubMed Central · doi:10.22038/ijbms.2019.33825.8051 · Cited by 20
“It is pyridine based, an aromatic, non-terpenoidal potent inhibitor of embryogenesis and adult emergence in insects (8).”
BackgroundStructure–Activity Relationships of Ecdysteroids and Non-Steroidal Ecdysone Agonists
Dinan, L. N., Nakagawa, Y., & Hormann, R. E. (2012) · Advances in insect physiology · doi:10.1016/b978-0-12-391500-9.00003-6 · Cited by 20
Eizaguirre, M., López, C., Schafellner, C., & Sehnal, F. (2007) · Archives of Insect Biochemistry and Physiology · doi:10.1002/arch.20181 · Cited by 20
Nishiura, J. T. (2002) · Annals of the Entomological Society of America · doi:10.1603/0013-8746(2002)095[0498:cmcimi]2.0.co;2 · Cited by 20
“In practical terms, juvenile hormone analogues, such as methoprene and pyriproxyfen, are effective insect growth regulators and are commercially used inmosquito control (Dhadialla et al. 1998).”
BackgroundSusceptibility of Diatraea saccharalis (Lepidoptera: Crambidae) to Tebufenozide
Rodriguez, L. M., Reagan, T. E., & Ottea, J. A. (2001) · Journal of Economic Entomology · doi:10.1603/0022-0493-94.6.1464 · Cited by 20
“It binds to the ecdysone receptor site after entering the hemocoel and activates the molting process causing the production of a new, but malformed, cuticle beneath the old cuticle (Wing et al. 1988, Dhadialla et al. 1998).”
BackgroundSmagghe, G. J., Braeckman, B. P., Huys, N., & Raes, H. (2003) · Journal of Applied Entomology · doi:10.1046/j.1439-0418.2003.00727.x · Cited by 20
Su, N., & Monteagudo, E. J. (2017) · Journal of Economic Entomology · doi:10.1093/jee/tox178 · Cited by 19
Alomar, A. A., & Alto, B. W. (2021) · Journal of Medical Entomology · doi:10.1093/jme/tjab193 · Cited by 19
Hormann, R. E., Smagghe, G. J., & Nakagawa, Y. (2008) · QSAR & Combinatorial Science · doi:10.1002/qsar.200730114 · Cited by 19
Soin, T., Geyter, E. D., Mosallanejad, H., Iga, M., Martı́n, D., Ozaki, S., Kitsuda, S., Harada, T., Miyagawa, H., Stefanou, D. T., et al. (2010) · Pest Management Science · doi:10.1002/ps.1903 · Cited by 19
Maïza, A., Kilani, S., Farine, J. P., Smagghe, G. J., Aribi, N., & Soltani, N. (2004) · PubMed · Cited by 19
Integrated management of tortricid pests of tree fruit
USDA-ARS, U., Knight, A. L., Judd, G. J. R., Agriculture and Agri-food Canada, C., Gilligan, T. M., USDA-APHIS-PPQ, U., Fuentes‐Contreras, E., Universidad de Talca, C., & Walker, W. B. (2019) · Burleigh Dodds series in agricultural science · doi:10.19103/as.2019.0046.19 · Cited by 19
Kumral, N. A., Kovancı, B., & Akbudak, B. (2007) · Journal of Pest Science · doi:10.1007/s10340-007-0185-6 · Cited by 19
“Moreover, the inaccuracy of such a traditional approach can be accounted for the reduced eYcacy of Insect Growth Regulators (IGR), such as diXubenzuron, and fenoxycarb, being safe to natural enemies, due to untimely application (Baldassari et al. 1997; Dhadialla et al. 1998; Medina et al. 2001, 2003).”
BackgroundLessard, J., Aicha, S. B., Fournier, A., Calvo, E. L., Lavergne, É., Pelletier, M., & Labrie, C. (2007) · The Prostate · doi:10.1002/pros.20559 · Cited by 19
“RSL1 is a member of a class of insecticides known as diacylhydrazines [13].”
Gelbič, I., Adel, M. M., & Hussein, H. M. (2011) · Open Life Sciences · doi:10.2478/s11535-011-0046-4 · Cited by 19
Minakuchi, C., Ogura, T., Miyagawa, H., & Nakagawa, Y. (2007) · Journal of Pesticide Science · doi:10.1584/jpestics.g07-19 · Cited by 19
Kontogiannatos, D., Swevers, L., Zakasis, G., & Kourti, A. (2014) · Ecotoxicology · doi:10.1007/s10646-014-1384-6 · Cited by 19
“cycle regulators such as cyclins (Dhadialla et al. 1998; Nakagawa et al. 2000; Smagghe et al. 2002).”
Cadogan, B. L., Scharbach, R. D., Krause, R. E., & Knowles, K. R. (2002) · Journal of Economic Entomology · doi:10.1603/0022-0493-95.3.578 · Cited by 19
Hagler, J. R. (1999) · CRC Press eBooks · doi:10.1201/9781439822685.ch7 · Cited by 19
“IGRs interfere with the endocrine system of the pest and affect their normal growth and development (Dhadialla et al., 1998).”
BackgroundInsect science – a vulnerable discipline?
Loxdale, H. D. (2016) · Entomologia Experimentalis et Applicata · doi:10.1111/eea.12421 · Cited by 20
“More precise control measures have also been tried, including use of synthetic juvenile hormones to disrupt development and subsequent reproduction (Dhadialla et al., 1998), synthetic or natural insect sex pheromones to specifically disrupt mating behaviour and success (Witzgall et al., 2010), and…”
Background
Metadata
- Authors
- Dhadialla, T. S., Carlson, G. R., & Le, D. P.
- Affiliations
- Insecticide Research Laboratories, Rohm and Haas Company, 727 Norristown Road, Spring House, Pennsylvania 19477;
- Venue
- Annual Review of Entomology
- Publisher
- Annual Reviews
- Published
- 1998-01
- Volume
- 43
- Issue
- 1
- Pages
- 545-569
- ISSN
- 0066-4170 (ISSN-L)
- 1545-4487
- OpenAlex
- W2149662691
- Cited by
- 912
- References
- 131
- Citations by year
- 2026: 12 · 2025: 29 · 2024: 29 · 2023: 22 · 2022: 23 · 2021: 44 · 2020: 22 · 2019: 30 · 2018: 23 · 2017: 34 · 2016: 32 · 2015: 28 · 2014: 21 · 2013: 32 · 2012: 49
- FWCI
- 3.70
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Annual Review of Entomology (publishedVersion)
- PubMed (publishedVersion)
- Topics
- Life Sciences › Agricultural and Biological Sciences › Plant Science › Insect Pest Control Strategies
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Insect Resistance and Genetics
- Life Sciences › Agricultural and Biological Sciences › Insect Science › Insect-Plant Interactions and Control
- Keywords
- insect growth regulators, ecdysteroid agonists, juvenile hormone agonists, tebufenozide, fenoxycarb, pyriproxyfen, 20-hydroxyecdysone, ecdysteroid receptor, insecticide mode of action, ecotoxicology, lepidopteran pests
- MeSH terms
- Animals, Forecasting, Hydrazines, Insecticides, Insecta, Juvenile Hormones, Steroids, Molecular Structure, Molecular Mimicry, Ecdysteroids
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