Alkyl 3,7,11-trimethyl-2,4-dodecadienoates, a new class of potent insect growth regulators with juvenile hormone activity

Henrick, Clive A.; Staal, Gerardus B.; Siddall, J. B.

doi:10.1021/jf60187a043

Cited by 195 publications

(97 citation statements)

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“…71) Considerable effort has been made to develop natural or synthetic JH analogs that are stable in the environment and resistant to metabolism. Several JH analogs such as methoprene (Zoecon), 72) fenoxycarb (Roche/Maag), 73,74) diofenolan (Ciba Geigy) 75) and pyriproxyfen (Sumitomo Chemical Co.) [76][77][78] have been synthesized and are commercially available as insect growth regulators (IGRs) (Fig. 3).…”

Section: Natural and Synthetic Jh Mimics As Insect Growth Regulatorsmentioning

confidence: 99%

Insect juvenile hormone action as a potential target of pest management

Minakuchi

Riddiford

2006

J. Pestic. Sci.

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Juvenile hormone (JH) is a sesquiterpenoid hormone that regulates growth and development in insects. Since JH is a hormone specific to insects and other arthropods, compounds disrupting JH action in insects are expected to be ideal insecticides with low toxicity to non-target organisms. Many natural or synthetic analogs with JH-like or anti-JH activity have been identified, and some potent JH mimics have been used as insecticides. Recent studies on the enzymes in JH biosynthetic and metabolic pathways should be helpful for the discovery of more potent analogs and for the establishment of new means of pest management using recombinant DNA technology. © Pesticide Science Society of Japan Keywords: juvenile hormone (JH), insect metamorphosis, insect growth regulators, biosynthesis and metabolism of JH. Review* To whom correspondence should be addressed. E-mail: chieka_minakuchi@yahoo.com © Pesticide Science Society of Japan doptera. 17,18) Higher Diptera such as D. melanogaster and the blowfly Calliphora vomitoria produce JH III bisepoxide. 19,20) A small amount of methyl farnesoate, a precursor of JH III, was found in cockroach embryos and larvae. [20][21][22] Methyl farnesoate has also been identified in crustaceans 23) and is thought to have a JH-like action in female reproduction. 24)12Ј-OH JH III identified from the corpora allata of the African locust Locusta migratoria migratorioides was reported to exhibit JH activity when a high dose of this compound was topically applied to Tenebrio pupae. 25,26) Biosynthesis, Transport and Metabolism of Juvenile HormoneIn insects, JH is synthesized in the corpora allata via the mevalonate pathway (Fig. 2).27) The mevalonate pathway also exists in mammals and plants, and the early steps from acetylCoA to farnesyl diphosphate are conserved among these organisms. Importantly, insects and other arthropods do not synthesize cholesterol de novo but have to acquire it from dietary sources because they lack the genes encoding squalene synthase and other subsequent enzymes of the sterol branch. 28,29) Another peculiarity of the mevalonate pathway in insects is the capacity to synthesize JH via the isoprenoid branch.The genes encoding the enzymes in the mevalonate pathway from acetyl-CoA to farnesyl diphosphate have been identified in the genome of D. melanogaster and the malaria mosquito Anopheles gambiae, and in an EST library of the pine engraver Ips pini.27) However, it has been difficult to identify the genes encoding enzymes from farnesyl diphosphate to JH

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Section: Natural and Synthetic Jh Mimics As Insect Growth Regulatorsmentioning

confidence: 99%

Insect juvenile hormone action as a potential target of pest management

Minakuchi

Riddiford

2006

J. Pestic. Sci.

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“…Several chemical companies have taken advantage of this characteristic and synthesized chemical analogs of JH (JHA) having insecticidal activity for certain insects (Staal, 1975;Mulla, 1995;Ritchie and Broadsmith, 1997). Perhaps the most successful JH analog is methoprene (isopropyl 11-methoxy-3, 7, 11-trimethyl-2, 4-dodecadienoate) (Henrick et al, 1973), which is very effective against dipteran insects (Staal, 1975;O'Donnell and Klowden, 1997). However, the wide use of methoprene for mosquito control in recent years is perhaps exacting a toll: resistance evolution.…”

Section: Introductionmentioning

confidence: 99%

Drosophila melanogaster Methoprene-tolerant (Met) gene homologs from three mosquito species: Members of PAS transcriptional factor family

Wang

Baumann

Wilson

2007

Journal of Insect Physiology

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The Methoprene-tolerant (Met) gene in Drosophila melanogaster has been shown to function in juvenile hormone (JH) action. Met homologs were isolated from three mosquito species, Culex pipiens, Aedes aegypti and Anopheles gambiae. Sequence similarity was found to be high in bHLH and PAS conserved domains, and the majority of the 7-9 introns in AaMet and AgMet are located in either identical or similar positions, indicating evolutionary relatedness. Sequence comparison with Met and the similar germ-cell expressed (gce) gene in D. melanogaster showed that the mosquito genes are more similar to gce than to Met. Moreover, the multiple introns in AgMet and AaMet are more similar in number with the 7 introns in Dmgce than to the single intron in DmMet; in fact, six intron positions in AaMet and AgMet are similar to those in Dmgce. Efforts to identify a second homologous gene in mosquitoes were unsuccessful, suggesting a single gene in lower Diptera, consistent with the single gene uncovered in genomic sequencing of Ae. aegypti and An. gambiae. These results suggest that a gene duplication occurred during the evolution of higher Diptera, resulting in Met and gce.

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“…Our continued interest in novel antiparasitic agents led us to screen extracts of fungal fermentations in in vitro antiparasitic assays using surrogate organisms such as blowfly larvae, Lucilia sericata [5], mosquito larvae, Aedes aegypti [6], and a parasitic nematode of sheep, Haemonchus contortus [7]. This screening strategy led to the isolation and identification of xanthonol (1), a new dimeric xanthone from an extract of a non-sporulating fungal species (Figure 1).…”

Section: Introductionmentioning

confidence: 99%