Cockroaches, American

In 1952, it was reported that a constituent of excretions from female American cockroaches of the species Periplaneta ameri-cana is an extraordinarily potent sex pheromone.1 Early attempts to isolate and characterize the active compounds were hampered because individual cockroaches store only minute amounts of the pheromone ( 1 pg), and a full 25 years elapsed before Persoons et al. reported the isolation of two extremely active compounds, periplanones A and B.2 The latter substance is present in larger relative measure and its germacranoid structure (1, without stereochemistry) was tentatively assigned on the basis of spectroscopic data. Thus, in 1976, the constitution of periplanone B was known but there remained a stereochemical problem of a rather serious nature. Roughly three years intervened between the report of the gross structure of periplanone B and the first total synthesis of this substance by W. C. Still at Columbia.3... 

Desilylation of 20, followed by oxidation of the secondary hydroxyl group furnishes racemic 1 in a yield of 81 %. Spectroscopic and bioassay characteristics of synthetic ( )-1 matched natural peripla-none B in every detail. The constitution and relative stereochemistry of the elusive American cockroach sex excitant periplanone B (1) has been secured in a very elegant way.5... 

Based on the successful series of transformations summarized in Scheme 1, Schreiber and Santini developed an efficient and elegant synthesis of periplanone B (1),8 the potent sex pheromone of the American cockroach, Periplaneta americana. This work constitutes the second total synthesis of periplanone B, and it was reported approximately five years after the landmark periplanone B synthesis by W.C. Still9 (see Chapter 13). As in the first synthesis by Still, Schreiber s approach to periplanone B takes full advantage of the facility with which functionalized 5-cyclodecen-l-one systems can be constructed via anionic oxy-Cope rearrangements of readily available divinylcyclohexanols.5 7 In addition, both syntheses of periplanone B masterfully use the conformational preferences of cyclo-decanoid frameworks to control the stereo- and regiochemical course of reactions carried out on the periphery of such ring systems.10... 

Blum and Kearns (1) showed in the American cockroach that topically applied pyrethrum shows a negative temperature coefficient of action between 15° and 35°C. The 24-hour LDso for pyrethrum is about 1 g. at 15°C. and about 6 Mg- at 35°C. 

One of the most remarkable recent achievements was the synthesis of periplanone-(B) (63) the sex excitant of the American cockroach. At the time the synthesis... 

Single abdominal injection of 1 mg famphur/kg BW whole-body residues of famphur, famoxon, and /V-desmethylfamphur measured 1 h after injection AMERICAN COCKROACH, Periptaneta americana Of total amount injected, 84.6% remained after 1 h 79.4% famphur, 2.2% famoxon, and 3.1% /V-desmethylfamphur 2... 

FIGURE 2 Pheromone structures of the American cockroach (periplanone B), the brownbanded cockroach (supellapyrone), bark beetles (ipsdienol enantiomers), and the cabbage looper moth (six acetates). 

As mentioned above, to apply to insects a conclusion drawn directly from tests on mammals may sometimes be misleading.3 For instance, American cockroaches have a remarkably high tolerance for acetylcholine,4 but, on the other hand, a substance showing some of the pharmacological properties of acetylcholine does accumulate in flies and cockroaches poisoned with D.D.T. Similarly, Hopf, working with locusts, was unable to demonstrate any increase in toxicity of eserine or T.E.P.P. resulting from the subsequent injection of acetylcholine. From this, Lord and Potter infer that acetylcholine may not be directly involved in the insecticidal action of organo-phosphorus compounds, either because the enzymes which hydrolyse acetylcholine are not inhibited to any considerable extent in vivo or because the functions performed by acetylcholine in mammals are performed by another substance in insects. 

March RB, Fukuto TR, Metcalf RL. 1957. Metabolism of p32-dithio-systox in the white mouse. m American cockroach. University of California, Citrus Experiment Station, Riverside, California MRID 83215. 

Nyctotherus ovalis (an anaerobic heterotrichons ciliate from the hindgut of an American Cockroach)... 

Figure 1.6 Nyctotherus ovalis (an anaerobic heterotrichous ciliate from the hindgut of an American Cockroach) hydrogenosome with mitochondrial-type cristae (white arrows) r putative ribosomes m membrane me methanogenic endosymbiont (methanogenic bacterium) (J.H.P. Hackstein, Catholic University of Nijmegen,The Netherlands).

Ritter, F. J., Briiggemann, I. E. M., Gut, J., and Persoons, C. J. (1982). Recent pheromone research in the Netherlands on muskrats and some insects pests introduced from America into Europe the muskrat, Odatra zibethicus, the American cockroach, Peri-planeta americana, and the beet army worm, Spodoptera exigua. American Chemical Society Symposium Series 190,107-130. 

Phenylethylamines. The properties of phenylethylamines have been investigated in some detail as stimulators of cAMP synthesis in homogenates of the CNS of the American cockroach (54 55), in the crayfish behavioral assay (31) and as inhibitors of the myogenic contraction of the locust ETi muscle (56) as shown in Table III. 

When less substituent positions are present STERIMOL can be used but in those cases there is often hardly any difference in results if compared with the MTD method. This is illustrated by our version of the QSAR of the insecticidal activity against American cockroaches of 36 substituted benzyl chrysanthemates. 

Table IV. Insecticidal activity against American cockroaches of 36 substituted benzvl chrvsanthemates. ...

Chlamys nipponensis (Japanese scallop) Mizuhopecten yessoensis (Yesso scallop) Mimachlamys nobilis Charybdis feriatus (crab) Homarus americanus (American lobster) Panulirus stimpsoni Homarus americanus (American lobster) Farfantepenaeus aztecus (pen a 1) Periplaneta americana (American cockroach) Dermatophagoides pteronyssinus (dust mite) Lepidoglyphus destructor Homo sapiens (human) Homo sapiens (human) Sus scrofa (pig) Oryctolagus cuniculus (rabbit)... 

Asturias, J. A., Gomez-Bayon, N., AriUa, M. C., Martinez, A., Palacios, R., Sanchez-Gascon, F., and Martinez, J. (1999). Molecular characterization of American cockroach tropomyosin (Periplaneta americana allergen 7), a cross-reactive aUergen. /. Immunol. 162, 4342 348. 

Pomes, A., Melen, E., Vailes, L. D., Relief, J. D., Arruda, L. K., and Chapman, M. D. (1998). Novel allergen structures with tandem amino acid repeats derived from German and American cockroach. /. Biol. Chem. 273, 30801-30807. 

AMERICAN COCKROACH, Periplaneta americana Baits containing 1.5% boric acid All dead in 6 days (6)... 

Sex pheromone of the American cockroach absolute configuration of periplanone-B. Journal of the American Chemical Society 101 2495-2498. 

Appel, A. G. and Rust, M. K. (1983). Temperature-mediated sex pheromone production and response of the American cockroach. Journal of Insect Physiology 29 301-305. Barth, R. H., Jr (1964). The mating behavior of Byrsotria fumigata (Guerin) (Blaberidae, Blaberinae). Behaviour 23 1-30. 

Bell, W. J. and Adiyodi, K. G. (1981). The American Cockroach. New York Chapman Hall. 

Bell, W. J. and Kramer, E. (1980). Sex pheromone-stimulated orientation of the American cockroach on a servosphere apparatus. Journal of Chemical Ecology 6 287-295. 

---