Synthesis and juvenile hormone activity of benzimidazolylterpenes possessing a 2,7-dimethyloctane skeleton

Benzimidazolylterpenes, possessing a 2,7-dimethyloctane skeleton showed IGR-activity on pupae of Tenebrio molitor L in laboratory tests: N-(7-methoxy-2,7-dimethyl-2-octenyl)benzimidazole showed the greatest activity.     

Ovicidal activity of juvenile hormone mimics in the bean bug,Riptortus pedestris

Insect juvenile hormone (JH) mimics (JHMs) are known to have ovicidal effects if applied to adult females or eggs. Here, we examined the effects of exogenous JHMs on embryonic development of the bean bug, Riptortus pedestris. The expression profiles of JH early response genes and JH biosynthetic enzymes indicated that JH titer was low for the first 3 days of the egg stage and increased thereafter. Application of JH III skipped bisepoxide (JHSB₃) or JHM on Day 0 eggs when JH titer was low caused reduced hatchability, and the embryos mainly arrested in mid- or late embryonic stage. Application of JHMs on Day 5 eggs also resulted in an arrest, but this was less effective compared with Day 0 treatment. Interestingly, ovicidal activity of synthetic JHMs was much lower than that of JHSB₃. This study will contribute to developing novel insecticides that are selective among insect species.     

Juvenile hormone III, hydroprene and a juvenogen as soldier caste differentiation regulators in three Reticulitermes species: potential of juvenile hormone analogues in termite control

The efficacy of juvenile hormone III (JH III) and two JH-mimicking compounds was compared in laboratory experiments with Reticulitermes lucifugus (Rossi), R. santonensis Feytaud and R. virginicus (Banks). Induction of presoldier, soldier and/or soldier-worker intercaste differentiation was taken as positive response to the treatment. The novel juvenogen, a fatty acid ester of a juvenoid alcohol, induced greatest soldier differentiation in all species tested, followed by hydroprene. JH III was less effective. Representatives of three Reticulitermes species showed similar trends in soldier induction rates. Differences in mortality in treatments of termites of the same species from different colonies with the same compound were observed and evidently were caused by differences in the conditions of respective colonies.     

Effect ofMelia azedarach fruit extract on juvenile hormone titer and protein content in the hemolymph of two species of noctuid lepidopteran larvae [insecta: Lepidoptera: Noctuidae]

The effect of an enriched methanolic extract ofMelia azedarach L. (Meliaceae) fruits on the size of the corpora allata (CA), the juvenile hormone (JH) titer and the protein content in the hemolymph of two lepidopteran pests in Egypt,Spodoptera littoralis (Boisd.) andAgrotis ipsilon (Hufn.), was studied. Different concentrations of the extract were incorporated into an artificial diet on which the larvae were allowed to feed. InS. littoralis, a significant reduction in the CA volume of larvae treated at the 1000 ppm extract levelvs that of control larvae was observed. In A.ipsilon, a reduction was found in the right CA gland only. Larvae of both species that had fed on a diet withMelia extract had a higher mean JH-II titer in the hemolymph than did control larvae. In both species, the content of hemolymph protein was decreased significantly after feeding for 6 days on a diet treated with concentrations above 50 ppm extract, followed by 6 days on a normal diet. The results show that aM. azedarach fruit extract has an effect on the neuroendocrine control in the insects. The effect on the hemolymph protein levels is discussed in connection with changes in the morphology/physiology of the gut.     

Effects of juvenile hormone analog formulations on development and reproduction in the bed bug Cimex lectularius (Hemiptera: Cimicidae)

BACKGROUND: Bed bugs (Cimex lectularius L.) have become a common insect pest in urban areas and are often difficult to manage. Eradication is made more problematic by widespread insecticide resistance, raising interest in alternative control products. Juvenile hormone analogs (JHAs) such as methoprene and hydroprene are relatively harmless to non‐arthropods and have proved to be effective against other urban insect pests. Two JHA products (Gentrol^® and Precor^®, Central Life Sciences, Schaumburg, IL) were tested for efficacy against various bed bug stages as direct spray and as dry residue using three bed bug strains. RESULTS: At 1× and 2× the label rate, Precor^® [active ingredient (S)‐methoprene] had no significant effect on the development or fecundity of bed bugs. At 2× the label rate, confinement to residues of Gentrol^® [active ingredient (S)‐hydroprene] had no significant effect, but residues at 3× and 10× the label rate caused a reduction in fecundity and impaired development. Field strains were more susceptible to the reproductive effects of (S)‐hydroprene than a long‐maintained laboratory strain. CONCLUSIONS: While JHAs are attractive alternatives for pest management because of their inherent safety and distinct mode of action, these JHA formulations would have little impact on bed bug populations without relabeling to allow for higher application rates. Copyright © 2012 Society of Chemical Industry     

Comparative testing of several juvenile hormone analogues in two species of locusts,Locusta migratoria migratorioides and Schistocerca gregaria

Effective treatment with juvenile hormone analogues (JHAs) of early penultimate or early last-instar locust hoppers induces a supernumerary ‘extra’ nymphal instar. These ‘extra’ nymphs, also termed ‘adultoids’, die in the course of, or shortly after, an ‘extra’ moult. Less effective treatment results in imperfect adults with crumpled twisted wings which presumably limit their flight and migratory abilities. Extremely effective treatment leads to death in the next moult. Comparing dose-response relations of (7S)-methoprene, fenoxycarb, pyriproxyfen and a new JHA, R70-1 (ethyl cis-N-{2-[4-(2-hydroxycyclohept-1-ylmethyl)phenoxy]ethyl}carbamate), we revealed that route of administration, instar of the recipient hopper, and species may alter over 1000-fold the ED₅₀ for the same JHA. Locusta migratoria migratorioides is much more susceptible to JHAs than Schistocerca gregaria. The lowest ED₅₀ found to induce adultoids and subsequent death in the ‘extra’ moult was 0·12 μg pyriproxyfen injected in olive oil to early penultimate instar hoppers of L. m. migratorioides (about 0·5 μg g^-1 fresh weight). R70-1 was more active than pyriproxyfen following the more practical topical application to early last-instar hoppers of L. m. migratorioides, 5·9 μg and 46 μg per hopper, respectively (about 10 μg g^-1 and 78 μg g^-1 fresh weight). The high susceptibility of last-instar L. m. migratorioides nymphs to topically applied R70-1 is promising from the practical standpoint. ©1997 SCI     

Inhibition of juvenile hormone biosynthesis in the tobacco hornworm, Manduca sexta, by a bisthiolcarbamate juvenoid and related compounds

Biosynthesis of juvenile hormone in the tobacco hornworm, Manduca sexta, is inhibited by the bisthiolcarbamate juvenoid N-ethyl-1,2-bis(isobutylthiolcarbamoyl)ethane both in vitro and in vivo. In vitro an extremely steep dose-response curve was obtained with an ID₅₀ value of 6 × 10^?6M. However, in vivo topical treatment with the compound resulted in mild JH antagonistic symptoms, suggesting rapid metabolism of the compound. In agreement with results from metabolic studies performed on plants and in mammals, sulfoxidation of the thiocarbamate S-(4-chlorobenzyl)N,N-diethylthiocarbamate resulted in an enhanced inhibitory effect on JH biosynthesis in vitro. This suggests that the corresponding thiocarbamate sulfoxides may act as intermediates in carbomylating critical thiol sites important in the terpenoid biosynthesis pathway. Furthermore, this study shows that these prototype compounds are interesting tools for further investigation of chemical inhibition of JH biosynthesis in insects.     

Juvenile hormonal activity of mono- and polyenehomobenzenes in Drosophila virilis, Spodoptera frugiperda and Araschnia levana

A series of mono- and polyenehomobenzenes was synthesised by a highly regioselective palladium-catalysed allylic alkylation of substituted and unsubstituted benzylic Grignard reagents employing catalytic amounts of catalyst and tested for juvenile hormone activity on the fruit fly Drosophila virilis Sturtevant (Diptera: Drosophilidae), on an important agricultural pest species, the fall armyworm Spodoptera frugiperda JE Smith (Lepidoptera: Noctuidae), and on the map butterfly Araschnia levana L. (Lepidoptera: Nymphalidae). In D. virilis only polyenehomobenzenes with a geranyl chain and a methyl, methoxy or isopropyl group at the para position of the aromatic ring displayed significant juvenile hormonal activity at low doses. A monoenehomobenzene and polyenehomobenzenes with longer allylic chains or without a substituted aromatic ring were not active. In S. frugiperda and in A. levana, a mono-, a di- and a tetraene displayed juvenile hormonal activity. In the lepidopteran species, a trend for the necessity of a substitution at position 4 of the phenyl group for high juvenile hormonal activity was also found.     

A comparative study of the metabolic effects of hypertrehalosemic hormone and 1,2,3,4,5,6-hexachlorocyclohexane (γ-HCH) in the American cockroach, Periplaneta americana

Several effects of hypertrehalosemic hormone (Peram-HTH) have been compared with the action of 1,2,3,4,5,6-hexachlorocyclohexane (γ-HCH) in the cockroach, Periplaneta americana. The data show that both agents stimulate respiration while maintaining an R.Q. of approximately 1. The action of γ-HCH differs from that of Peram-HTH-I in that it promotes oxidation of large amounts of soluble carbohydrate. Recent studies show that Peram-HTH-I has an equally potent stimulatory effect on lipid deposition in the fat body and on the release of trehalose from the same tissue. It is of interest that γ-HCH not only increases triacylglycerol accumulation in the fatγ body but that this effect is more pronounced if the γ-HCH is applied to the ventral surface of the mesothorax. γ-HCH also depleted whole body glycoprotein and glycolipid whereas Peram-HTH-I had no effect on glycoprotein but increased that of glycolipid. It is clear that γ-HCH causes complex disruptions to the metabolism of the insect, many of which are related to the release of hormones. The study supports the idea that certain actions of γ-HCH are mediated through the release of Peram-HTH-I.     

Resistance of codling moth, Cydia pomonella (L.) (Lepidoptera: Tortricidae), larvae in Michigan to insecticides with different modes of action and the impact on field residual activity

BACKGROUND: The codling moth is one of the principal pests of apple in the world. Resistance monitoring is crucial to the effective management of resistance in codling moth. Three populations of codling moth in neonate larvae were evaluated for resistance to seven insecticides via diet bioassays, and compared with a susceptible population. In addition, apple plots were treated with labeled field rate doses of four insecticides. Treated fruit were exposed to neonate larvae of two populations from commercial orchards. RESULTS: Two populations of codling moth expressed two‐ and fivefold resistance to azinphos‐methyl, seven‐ and eightfold resistance to phosmet, six‐ and tenfold resistance to lambda‐cyhalothrin, 14‐ and 16‐fold resistance to methoxyfenozide and sixfold resistance to indoxacarb, but no resistance to acetamiprid and spinosad. The impact of the resistance to azinphos‐methyl, measured as fruit damage, increased as the insecticide residues aged in the field. In contrast, fruit damage in methoxyfenozide‐ and lambda‐cyhalothrin‐treated fruit was observed earlier for resistant codling moth. No differences in efficacy were found for acetamiprid. CONCLUSIONS: Broad‐spectrum insecticide resistance was detected for codling moth. Resistance to azinphos‐methyl, lambda‐cyhalothrin and methoxyfenozide was associated with reduced residual activity in the field. Broad‐spectrum resistance presents serious problems for management of the codling moth in Michigan. Copyright © 2008 Society of Chemical Industry