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

BACKGROUND: A series of juvenoid alcohols and their glycosidic derivatives (juvenogens), synthesized at the Institute of Organic Chemistry and Biochemistry in Prague, commercially used juvenoids and the natural derivatives of juvabione were evaluated for their systemic juvenilizing effect on the red firebug, Pyrrhocoris apterus L., and on the pea aphid, Acyrthosiphon pisum Harris. A life table response experiment was designed, and demographic characteristics were computed for a cohort of A. pisum following chronic exposure to a range of concentrations of the selected trans-isomer of carbamate juvenoid 8 applied via the broad bean (Vicia faba L.) root system. RESULTS: Using the ratio of topical and per os activities, promising effects were found in two alkyl beta-D-glucopyranosides (3 and 9) and the trans-isomer of carbamate juvenoid 8 in tests on P. apterus. In A. pisum, the highest systemic activity was found in tests with the trans-isomer of carbamate juvenoid 8. The longevity, the number of offspring per female and the number of offspring per reproducing female significantly decreased with concentrations of 0.05 mg mL(-1) and higher. While the net reproductive rate R(0) and the intrinsic rate of natural increase r(m) displayed similar trends, the generation time G varied slightly between 11.6 and 12.8 days. CONCLUSION: 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.

Insect pest management agents: hormonogen esters (juvenogens).

The chemical part of this investigation focused on designing structures and synthesizing a series of six new esters (juvenogens), derived from biologically active insect juvenile hormone bioanalogues (juvenoids, JHAs) and unsaturated short-chain linear and branched fatty acids for possible application as biochemically targeted insect hormonogen agents. The structures of the new compounds were assigned on the basis of a detailed NMR analysis of their (1)H and (13)C NMR spectra. The biological part of this investigation focused on introductory biological screening tests with these compounds against the red firebug (Pyrrhocoris apterus), termites (Reticulitermes santonensis and Prorhinotermes simplex), and the blowfly (Neobellieria bullata). The biological activity of the juvenogens was studied in relation to the fatty acid functionality in the structures. Notable biological activity in topical tests and medium activity in peroral tests was found for the juvenogens 3 and 7 with P. apterus. The compounds 6 and 8 showed the lowest activity in both topical and oral assays with P. apterus. Considerable effect of all tested juvenogens was observed in P. simplex; however, the juvenogens 5 and 6 (derivatives of the only branched short-chain fatty acid) showed no activity against R. santonensis. The effect of the compounds 3-8 on larval hatching of N. bullata was only moderate (larval hatching 80-90%); however, the proliferation effect caused by 5, 6, and 8 is more pronounced than the effect caused by 3, 4, and 7.

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.

Can juvenogens, biochemically targeted hormonogen compounds, assist in environmentally safe insect pest management?

Two different types of juvenogens, biochemically targeted hormonogen compounds were tested for their potency to act as insect pest management agents. In the performed biological screening, wax-like esteric juvenogens (3-10) proved to be convenient agents for controlling blowfly and termites, and displayed species selectivity: cis-N-{2-[4-(2-butanoyloxycyclohexyl)methyl]phenoxy}ethyl carbamate (3) was highly active on blowfly (Neobellieria bullata), while trans-N-{2-[4-(2-hexadecanoyloxycyclohexyl)methyl]-phenoxy}ethyl carbamate (6) showed high activity on termite (Prorhinotermes simplex). Glycosidic juvenogens, isomeric N-{2-{4-{[2-(beta-D-galactopyranosyloxy)cyclohexyl]methyl}phenoxy}ethyl carbamates (13 and 14), were proved to act as systemic agents, suitable for protecting plants against phytophagous insects (e.g. aphids). Due to the prolonged action of juvenogens, which is connected with the sequential liberating of the biologically active molecule of the insect juvenile hormone bioanalog from the juvenogen molecule by means of enzymic systems of target insects and/or their host plants, more insect individuals can be treated by juvenogens, which are species-targeted structures due to their different physicochemical properties. The results achieved with both types of juvenogens were promising, concerning their final effect on the tested insect species, and the compounds 3-6, 9 (cis-(9Z)-N-{2-[4-(2-(octadec-9-enoyl)oxycyclohexyl)methyl]phenoxy}ethyl carbamate), 13 and 14 proved to represent convenient insect pest management agents for potential practical applications against different insect pests.

Residues of diflubenzuron on horse chestnut (Aesculus hippocastanum) leaves and their efficacy against the horse chestnut leafminer, Cameraria ohridella.

Residues of the insect growth regulator diflubenzuron were quantified on horse chestnut (Aesculus hippocastanum L.) leaves treated with a diflubenzuron 480 g litre(-1) SC, Dimilin. To analyse the samples, an analytical procedure was developed involving a simple extraction step followed by high-performance liquid chromatography on an octadecyl-modified silica column with methanol + 0.01 M ammonium acetate mobile phase. The results showed diflubenzuron to be highly stable on horse chestnut leaves; more than 4 months (127 days) after application, 38% (on average) of the insecticide still remained on/in the leaves. The data confirmed biological observations showing diflubenzuron's long-term efficacy against the horse chestnut leafminer, Cameraria ohridella Deschka and Dimic, which is the most important pest of the horse chestnut in Europe. The hypothesis of possible penetration of diflubenzuron into the leaf mass is explored and discussed.

Juvenogens as potential agents in termite control: laboratory screening.

Preliminary screening tests of eight juvenogens, fatty acid esters of two parent juvenoid alcohols, showed high juvenilizing effect in the termite Prorhinotermes simplex (Hagen). This effect is manifested by differentiation of termite workers into pre-soldiers, soldiers and/or soldier-intercastes ('soldiers'). Juvenogen 9 was tested with five other termite species: Zootermopsis angusticollis Hagen, Kalotermes flavicollis F, Cryptotermes declivis Tsai & Chen, Reticulitermes santonensis de Feytaud, and R flaviceps Oshima, and showed promising efficacy in force-feeding (FF) as well as in choice bioassays. In the economically important subterranean termites R santonensis and R flaviceps, after application of 0.5 mg ml(-1) in FF experiments ca 57 and 73%, respectively, of workers changed into soldiers. In Zootermopsis angusticollis application of 0.05 mg ml(-1) caused differentiation in 62% soldiers, and 57% soldiers differentiated after topical application of 1 microg of the tested compound per termite. Differentiation of excessive soldiers induced by a juvenile hormone-mimicking compound may cause disruption of the social structure and ultimately the death of the colony.

Fatty acid esters of juvenoid alcohols as insect hormonogen agents (juvenogens).

A series of 8 new juvenogens (3--10) was prepared starting from a pair of isomeric insect juvenile hormone bioanalogues ( and ). The biological activity of the juvenogens -- was tested for their effect on reproduction of the blowfly Neobellieria (Sarcophaga) bullata and for the juvenilizing activity on the termite Prorhinotermes simplex. Results of biological screening are important in structure--activity studies and promising for potential practical application of some of the juvenogens studied, especially against termites.