Juvenile Hormone Activity of Some Glycosidic Juvenogens

Sláma, Karel; Wimmer, Zdeněk; Romaňuk, M.

doi:10.1515/bchm2.1978.359.2.1407

Cited by 17 publications

(6 citation statements)

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“…The difference in efficacy of the cis ‐isomers and trans ‐isomers of both structural types of JHA on P. apterus is in agreement with the results for the related pyrrhocorid species D. cingulatus reported earlier 12, 18. The inactivity of the β‐ D ‐glucopyranoside derivative of α, β‐unsaturated esteric juvenoid ( 3 ) when applied topically was also confirmed.…”

Section: Discussionmentioning

confidence: 99%

“…1a), bearing hydroxyl functionality at the 1,2‐disubstituted cyclohexane ring, which results in synthesis and separation of the cis ‐ and trans ‐isomers of the alcoholic juvenoids ( 1 and 2 ) 28. The alcoholic juvenoids were transformed into their alkyl β‐ D ‐glucopyranoside derivatives ( 3 and 4 )18 and β‐ D ‐galactopyranoside derivatives ( 5 and 6 ) 29. The second structural type is represented by cis ‐ and trans ‐isomers of juvenoids ( 7 and 8 ),30 bearing carbamate functionality in the aliphatic side chain of their molecules (Fig.…”

Section: Methodsmentioning

confidence: 99%

“…Per os (O) application was achieved using the drinking assay described by Sláma et al 18 Each compound was diluted with water into four concentrations (0.025, 0.25, 2.5 and 25 µg in 55 µL) and offered to insects during the last larval instar. The dilution rate was based on the knowledge that water consumption of final‐stadium nymphs of P. apterus is approximately 55 µL per individual during the first 3 days following ecdysis (JH sensitive period) 32.…”

Section: Methodsmentioning

confidence: 99%

“…Hence, Sláma and Romaňuk16, 17 prepared fatty acid esters derived from alcoholic JHAs. The second type of juvenogen, glycosidic derivatives of the alcoholic JHAs, was first synthesized in 1978 18. The hormonally active component of these compounds is released after hydrolysis by glycosidases.…”

Section: Introductionmentioning

confidence: 99%

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The systemic effects of juvenoids on the red firebug Pyrrhocoris apterus and on the pea aphid Acyrthosiphon pisum with data on life table response

Jedlička

Kuldová

Wimmer

2007

Pest Management Science

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Expected systemic activity of glycosidic juvenogens in P. apterus was not confirmed by exposure of the pea aphid on broad bean treated with aqueous solutions of the compounds. Nevertheless, the carbamate juvenoid alcohol 8 displayed a considerable juvenilizing effect on A. pisum in screening tests. Furthermore, this compound indicated a sublethal effect as the realized fecundity U(x) decreased disproportionately to the age-specific survival L(x) with increased concentration. The population parameters are compared with the data in similar demographic studies and are discussed together with the possibilities of using the compounds of this structural type in practice.

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Section: Discussionmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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The systemic effects of juvenoids on the red firebug Pyrrhocoris apterus and on the pea aphid Acyrthosiphon pisum with data on life table response

Jedlička

Kuldová

Wimmer

2007

Pest Management Science

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“…In contrast, hydrolysis of glucose conjugates catalyzed by S-glucosidase is particularly active in piercingsucking insects, and is probably responsible for the selective activation of glucosidic juvenogens in Dysdercus and A. pisum (Slama and Romanuk, 1976;Slama et al, 1978;Robinson, 1956).…”

Section: Metabolism Of Pesticides and Other Synthetic Toxicantsmentioning

confidence: 99%

Molecular Aspects of Insect-Plant Associations

Brattsten¹,

Ahmad²

1987

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All rights reservedNo part of this book may be reproduced, stored in a retrieval system, or transmitted in any form or by any means, electronic, mechanical, photocopying, microfilming, recording, or otherwise, without written permission from the Publisher PREFACE Thanks to the meticulous and enthusiastic work of insect collectors and taxonomists over the past hundred years and more, we have today a large amount of information on the feeding habits and life styles of several hundred thousands of insect species.Insects that feed on plants during at least one of their life stages constitute about half of the three-quarters of a million described species. Their numbers both in terms of species and individuals together with their small but macroscopic sizes makes the insect-plant biological interface perhaps the most conspicuous, diverse and largest assemblage of intimate interspecies interactions in existence. It is also perhaps the most important biological interface because of the plants' role as primary producers upon which all other forms of earthly life depend, thereby bringing herbivorous insects occasionally into direct competition with human food and fiber production.Early enthusiasm revealed many remarkable specializations and associations between insects and plants, and occasionally assigned chemical mediators for them. However, the modern practices of large scale crop protection by synthetic pesticides and their attendant problems, particularly with resistance in "pests" and destruction of natural enemies, have been in large measure responsible for drawing our attention to the mechanisms whereby plants control insect populations and insects adapt to the plants' defenses.These practices have also brought home the importance of chemical mediators in practically all aspects of insect activities and, in particular, the importance of plant allelochemicals in maintaining and balancing insect-plant associations.There are about 20,000 identified allelochemicals to date, estimated to be between ten and 50 percent of all possible such non-nutrient chemicals.Most of these have biological activity, mostly uncharacterized, when accumulated in sufficiently high concentrations.Many are acutely toxic to insects and other animals. A few have been used successfully for insect control and as drugs; more importantly, however, plant allelochemicals continue to provide model structures for the development of synthetic insecticides and drugs.With the recent availability of high-resolution analytical instruments, natural history is rapidly turning into a modern, multidisciplinary biological science. The elucidation of the mechanisms which maintain the observed ecological equilibria in the insect-plant interface provide fascinating work and rich intellectual rewards. It is also necessary to understand these interactions for purposes of local food and fiber production, the premise being that understanding the molecular details of insect adaptations to plant allelochemicals may allow manipulations of those mechanisms for crop protec...

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Propesticides

Ujváry¹

2002

Encyclopedia of Agrochemicals

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For most pesticides, the chemically intact active ingredient of the marketed formulation is responsible for the biological activity at the molecular level. In some cases, however, the actual substance responsible for the desired effect is a chemically transformed product of the pesticide that was applied in the field. Such transformations are activation processes usually involving enzymes characteristic to the target organism, but the conversion can occur in the environment and by nonenzymatic processes. The expected biological activity is typically observable only in studies with whole organisms or in the field. The increase in selective toxicity for the target and nontarget organisms results from differential uptake, translocation, and metabolism of such pesticide precursors or propesticides. Selectivity, thus, increased safety, of neurotoxic insecticides can be achieved by incorporation of specific sulfur functionalities into the parent compound. Differential phytotoxicity of several classes of herbicides is based on selective oxidative and hydrolytic degradations in various plants. Hydrolysis and reduction are involved in the bioactivation of several profungicides. Bioactivation processes are also important for some organic and inorganic rodenticides. Although in many cases the propesticide nature of a compound was discovered during structure optimization and metabolism studies, there are several examples where incorporation of metabolically labile moieties into an insufficiently selective lead compound was crucial for commercial development.

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Juvenile Hormone Activity of Some Glycosidic Juvenogens

Cited by 17 publications

References 4 publications

The systemic effects of juvenoids on the red firebug Pyrrhocoris apterus and on the pea aphid Acyrthosiphon pisum with data on life table response

The systemic effects of juvenoids on the red firebug Pyrrhocoris apterus and on the pea aphid Acyrthosiphon pisum with data on life table response

Molecular Aspects of Insect-Plant Associations

Propesticides

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