Insect Juvenile Hormone Analogs Research Articles

Synthesis of Insect Juvenile Hormone Analogs, III. Synthesis of Juvenoids Containing a 2,6‐Dienoic Ester Function and a Terminal Pinene Ring System

AbstractThe synthesis of 2,6‐dienoic ester insect juvenile hormone analogs with a pinene ring in the terminal position is presented.

Competition between juvenile hormone antagonist precocene II and juvenile hormone analog: Methoprene in the nematode Caenorhabditis elegans

Precocene II causes a high adult mortality and a drastic growth reduction of growing Caenorhabditis elegans larvae. Symptoms caused by precocene II were partly reversible by the insect juvenile hormone analog methoprene, suggesting a physiological role of juvenile hormones in nematodes.

Susceptibility of Sitotroga cerealella (Oliv.) (Lepidoptera: Gelechiidae) to two insect juvenile hormone analogues

The effect of topical application of the insect juvenile hormone analogues methoprene (isopropyl-11-methoxy-3,7-11-trimethyl dodeca-2,4-dienoate) and hydroprene (ethyl-3,7,11-trimethyl dodeca-2,4-dienoate) on last instar larvae and newly-formed pupae of Sitotroga cerealella was examined. Topical application of methoprene at 10 μg/pupa to maize grains containing pupae resulted in 94% adult emergence whereas the same treatment applied to pupae removed from the grains reduced adult emergence to 45%. At 100 μg methoprene/pupa, adult emergence was 91% when grains containing pupae were treated and 32% when pupae were treated after removal from grains. Hydroprene (10 μg/pupa) was more effective than methoprene against insects both inside grains and after removal from grains, giving adult emergence of 48% and 8% respectively. At 100 μg/pupa, hydroprene completely prevented adult emergence when applied to insects removed from the grain. After treatment of the pupal stage with 10 or 100 μg methoprene per insect, adult males produced the same numbers of spermatophores as untreated males and the treatment did not affect either the number or fertility of eggs deposited by adult females.

Cyclic analogues of insect juvenile hormone

The preparation and the juvenilization effect of some derivatives of 3,7-dimethyl-9-(5-methyl-2-oxolanyl)-2,6-nonadenoic, 3,7-dimethyl-9-(5-methyl-2-oxolanyl)-2-nonenoic (methyl, ethyl and isopropyl ester, monomethyl and dimethylamide) and 3,7-dimethyl-9-(-methyl-2-oxolanyl)-2,4-nonadenoic acid (methyl, ethyl and isopropyl ester) have been described.

The chemistry of thujone. II. Insect juvenile hormone analogues via acid dianion coupling. The β lactone route

Several stereoselective syntheses of (E)-2-ethyl-6-methyl-5-octenoic acid (17) are described. The dianion of pure 17 was subsequently coupled with (E)-β-thujaketonic acid methyl ester (5), derived from thujone (1), to give the β-lactones 45 and 46 which were then epoxidized and pyrolyzed exemplifying a route to juvenile hormone analogues such as 51 and 54.

ChemInform Abstract: SYNTHESIS OF INSECT JUVENILE HORMONE ANALOGS. PART I. 4‐(1‐CYCLOHEXENYL)‐2‐BUTANONE AND 4‐(1‐METHOXYCYCLOHEXYL)‐2‐BUTANONE

Chemischer InformationsdienstVolume 10, Issue 2 Isocyclic Compounds ChemInform Abstract: SYNTHESIS OF INSECT JUVENILE HORMONE ANALOGS. PART I. 4-(1-CYCLOHEXENYL)-2-BUTANONE AND 4-(1-METHOXYCYCLOHEXYL)-2-BUTANONE L. BOROWIECKI, L. BOROWIECKISearch for more papers by this authorA. KAZUBSKI, A. KAZUBSKISearch for more papers by this author L. BOROWIECKI, L. BOROWIECKISearch for more papers by this authorA. KAZUBSKI, A. KAZUBSKISearch for more papers by this author First published: January 9, 1979 https://doi.org/10.1002/chin.197902144Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinkedInRedditWechat No abstract is available for this article. Volume10, Issue2January 9, 1979 RelatedInformation

Biological activity of insect juvenile hormone analogues against the stable fly and toxicity studies in domestic animals.

The insect JHAs are effective inhibitors of adult stable fly development. Laboratory and field evaluation studies demonstrated that area application of the analogues to larval breeding sites was efficacious for stable fly control in cattle feed lots and in marine grasses. Analytical methods by quantification with gas chromatography with flame ionization detection was developed to measure residual properties as well as aging and leaching in fly breeding media. The analogues did not interfere with the oviposition and development of the endoparasites, M. raptor and S. endius. Toxicity studies against swine, hamsters, and sheep showed that when compounds of high purity were used that no toxic effects were observed in any of the species.

Insect juvenile hormone analogs in conifers. III. Variability of Douglas-fir wood extractives with geographical location

Cores, branch wood, and foliage samples were taken from five healthy Douglas-fir trees at each of 20 sites across southern British Columbia, ranging from central Vancouver Island to the western slopes of the Rocky Mountains. Hybridization values for each tree were established by von Rudloff, based on the composition of the foliage essential oil. Branch wood samples and cores from bole wood were analyzed for lipophilic extractives content; the presence of juvabione-type insect juvenile hormone analogs (IJHA) was noted. A strong negative correlation was noted between lignin content and a hybrid index and a strong positive association between lignin content and diameter. There was a strong positive relationship between extractive content and age. Juvenile hormones were most commonly found in trees of the coastal and coastal intermediate subvariants. Branch wood and bole wood samples usually gave comparable results for the presence of the juvenile hormones.

Binding specificity of the juvenile hormone carrier protein from the hemolymph of the tobacco hornworm Manduca sexta Johannson (Lepidoptera: Sphingidae).

A series of analogues of insect juvenile hormone (four geometric isomers of methyl epoxyfarnesenate, several para-substituted epoxygeranyl phenyl ethers, and epoxyfarnesol and its acetate and haloacetate derivatives) was prepared to investigate the binding specificity of the hemolymph juvenile hormone binding protein from the tobacco hornworm Manduct sexta. The relative binding affinities were determined by a competition assay against radiolabeled methyl (E,E)-3,11-dimethyl-7-ethyl-cis-10,11-epoxytrideca-2,6-dienoate (JH I). The ratio of dissociation constants was estimated by plotting competitor data according to a linear transformation of the dissociation equations describing competition of two ligands for a binding protein. The importance of the geometry of the sesquiterpene hydrocarbon chain is indicated by the fact that the binding affinity is decreased as Z (cis) double bonds are substituted for E (trans) double bonds in the methyl epoxyfarnesenate series; the unepoxidized analogues do not bind. A carboxylic ester function is important although its orientation can be reversed, as indicated by the good binding of epoxyfarnesyl acetate. In the monoterpene series, methyl epoxygeranoate shows no affinity for the binding protein, but substitution of a phenyl or p-carbomethoxyphenyl ether for the ester function imparts a low, but significant affinity. These data taken together with earlier results indicate that the binding site for juvenile hormone in the hemolymph binding protein is characterized by a sterically defined hydrophobic region with polar sites that recognize the epoxide and the ester functions.

Occurrence of juvabione-type and epijuvabione-type sesquiterpenoids in Abies alba

The petrol-soluble fractions from the branchwood of four Abies alba trees were examined. Only two trees contained sufficient amounts of ‘juvabione-type’ insect juvenile hormone analogues for isolation and characterization. The first contained juvabione (4 R, 1′ R), 4′-dehydrojuvabione (4 R, 1′ R) and its 4 R, 1′S diastereomer in a ratio of 3:1, and juvabiol (4 R, 1′ R, 3′ S), isojuvabiol (4 R, 1′ R, 3′ R) and epijuvabiol (4 R, 1′ S, 3′ S) in an approximate ratio of 7:3:2. 4′-Dehydroepijuvabione (4 R, 1′ S) was the only ‘juvabione-type’ compound ioslated from the second tree. If it is accepted that juvabione and epijuvabione are enzymatically reduced forms of dehydrojuvabione and dehydroepijuvabione, respectively; then for these two A. alba our results indicate that only one enzyme which is specific for R chirality at C-1′ is present, since epijuvabione is not observed.

Occurrence of juvabione-type or epijuvabione-type insect juvenile hormone analogues in three Czechoslovakian firs

a Fisheries and Environment Canada, Forestry Directorate Western Forest Products Laboratory, Vancouver, British Columbia, V6T 1 X2, Canada, b Forest Research Institute Zvolen, Experiment Station Banskti Stiavnica, Czechoslovakia, C Institute of Entomology, Czechoslovak Academy of Sciences, 16609 Praglle 6, Czechoslovakia, and d Prairie Regional Laboratory, National Research Council, Saskatoon, Saskatchewan , S7 N 0 W9, Callada

Characterization of a metabolite-cytochrome P-450 complex derived from the aerobic metabolism of an insect juvenile hormone analog by rat microsomal fractions

The juvenile hormone analog, ( E)-4-[(6,7-epoxy-3,7-dimethyl-2-nonenyl)oxyl]-1,2-(methylenedioxy)benzene (RO-20-3600), was aerobically metabolized by and formed a metabolite complex with hepatic microsomal cytochrome P 450 in vitro and in vivo. The K m for the formation of the complex with hepatic microsomal cytochrome P 450 obtained from rats pretreated with phenobarbital was 74 μ m. The complex, once formed, is stable and cannot be discharged by treatment with either CO, potassium ferricyanide, peroxide, or dithionite. The complex has two spectral forms: with oxidized cytochrome P 450 (Fe +3), it has a single Soret band centered at 442 nm; with reduced cytochrome P 450 (Fe +2), it has Soret bands centered at about 427 and 455 nm. The results obtained when the spectral properties of the metabolite complex, its rate for formation, and its effects on drug metabolism were studied suggest that the complex may be involved with and/or responsible for the juvenile hormone properties of RO-20-3600. The metabolite complex inhibits a significant amount of cytochrome P 450 and most likely prevents the metabolism of endogenous juvenile hormone in insects.

Juvabione and its analogues. II. Isolation, identification, and occurrence of juvabiol and its epimer isojuvabiol from the whole wood of Abies balsamea

Epimeric mixtures of juvabiol (3a) and isojuvabiol (4a) have been detected in six North American Abies balsamea (L.) Mill. trees and isolated from the whole-wood extract of three. These juvabione related alcohols are insect juvenile hormone analogues with selective action typical of juvabione (1) and Δ4′-dehydrojuvabione (2). The widespread occurrence of these alcohols indicates that the original 'paper factor' was not due to 1 alone, nor was it due to a mixture of 1 and 2. In addition a fifth IJHA with selective action, Δ3′-dehydrojuvabi-5′-ol (5), was detected in the hot ethanol extract of four trees and isolated from one tree. It is shown that 5 is an allylic rearrangement product of the Δ4′-dehydrojuvabiols 6a and 7a. Mixtures of campesterol and sitosterol are the major crystalline components present in all the petroleum ether soluble extracts.

Cyclic analogues of insect juvenile hormone

Cyclic analogues of insect juvenile hormone

Some other cyclic analogues of the insect juvenile hormone

Some other cyclic analogues of the insect juvenile hormone

Acute Toxicity to Juvenile Rainbow Trout (Salmo gairdneri) of Naturally Occurring Insect Juvenile Hormone Analogues

Median lethal concentrations (LC50) of four insect juvenile hormone analogues (IJHA) for juvenile rainbow trout (Salmo gairdneri) were measured in bioassays with 4-h solution renewal. The most toxic compound tested was Δ4′-dehydrojuvabione, with a 48-h LC50 of 1.4 mg/liter and an estimated 96-h LC50 of approximately 0.8 mg/liter. Juvabione, epimeric mixtures of dihydrojuvabiones, and epimeric mixtures of juvabiols had 96-h LC50’s of 1.5, 1.8, and 2.0 mg/liter, respectively. All fish, including those that survived for 96 h, became lethargic soon after exposure to solutions of the IJHA, and their skins darkened. The toxicants were unstable in aqueous solution.

Effect of a juvenile hormone analogue on phosphatase activity in pupae of the stable fly, Stomoxys calcitrans

The alkaline phosphatase activity of stable fly pharate pupae treated with 10 ng of an insect juvenile hormone analogue (JHA), Stauffer R-20458, or untreated pupae was rhythmic and peaked 48 and 96 hr after larval-pupal apolysis. Those treated with 10 μg were not rhythmic and peaked at 48 and 120 hr. Acid phosphatase activity showed a general increase throughout pupal-adult transformation and was three- to four-fold higher than alkaline phosphatase activity. At 24 and 48 hr after larval-pupal apolysis, acid phosphatase was lower in the treated animals, but at 72 and 120 hr, it was higher. Neither inhibition nor enhancement of acid and alkaline phosphatase activity or by three other JHAs could be demonstrated in vitro.

Cross-resistance to an insect juvenile hormone analogue in a species of the Anopheles gambiae complex resistant to insecticides.

A classification based mainly on the characteristics of the presumptive adult eyes is described for the various stages of the 4th-instar larva of species A of the Anopheles gambiae complex. The stage most sensitive to a 24-hr exposure to ZR 515, a juvenile hormone analogue, is the mature 4th-instar (IV-D) larva. Both dieldrin and DDT/dieldrin-resistant strains of Anopheles “gambiae” species A showed marked cross-resistance to ZR 515, although a DDT-resistant strain did not.

Approaches to the synthesis of the insect juvenile hormone analog ethyl 3,7,11-trimethyl-2,4-dodecadienoate and its photochemistry.

Approaches to the synthesis of the insect juvenile hormone analog ethyl 3,7,11-trimethyl-2,4-dodecadienoate and its photochemistry.

Cholesterol and bile acids via acetate from the insect juvenile hormone analog methoprene

Metabolism of the insect growth regulator methorpene by a steer produced labeled cholesterol, cholic acid, and deoxycholic acid. Cholesterol and deoxycholic acid were degraded chemically by Kuhn-Roth and Barbier-Wieland oxidations to show catabolism of [5- 14C] methoprene to [2- 14C] acetate. Unless radioactive residues are rigorously characterized as primary metabolites rather than natural products, misinterpretations will occur when assessing metabolic pathways for extremely biodegradable compounds such as methoprene.