Moths, The

Phenazine-l-carboxamide (137) is known as oxychlororaphine and has been isolated from cultures of Pseudomonas chlororaphisit has some limited inhibitory properties, but the inhibitory action of phenazines is generally disappointing. Some phenazine derivatives have insecticidal properties thus, phenazine itself has been found to be toxic to the clothes moth, the Hawaiian beet webworm, the rice weevil and larva of the codling moth, but under trial conditions its toxicity to plant material, as evidenced by severe burning of foliage, was found to be too high to make it of practical value. 

A //sutji = 73 kJ/mol), a crystalline white solid that sublimes to produce a vapor that repels moths. The purple color of the gas above iodine crystals in a closed container provides visible evidence that this solid also sublimes at room temperature (A/7sutl = 62.4kJ/mol). 

A further finding concerns the stereochemistry of HD and its derivation from PA. Both HD and the primary PAs (monocrotaline, usaramine) that we know to be available to Utetheisa in the field are of the same (7R) stereochemical configuration. It was therefore not surprising to find that Utetheisa is unable to convert a PA of opposite (7S) stereochemistry (heliotrine) into HD. However, we found another arctiid moth, the Asian species Creatonotus transiens, which also produces HD in its coremata, to be able to use 7R and 7S PAs interchangeably for HD production (31). We are tempted to conclude that Creatonotus, unlike Utetheisa, has dietary access to PAs of both stereochemical configurations in its environment. 

Currently there are few insecticides registered as surface treatments to control stored-product insects. For years the organophosphate insecticide malathion was used as a surface treatment for structural facilities, but stored-product insects throughout the world have developed extensive resistance to malathion (Subramanyam and Hagstrum, 1996). Most of the resistance reports were generated from studies with bulk grains, but in the United States, resistance has been documented for field populations of the red flour beetle, T. castaneum (Herbst), and the confused flour beetle, T. confusum (DuVal), collected from flour mills (Arthur and Zettler, 1991, 1992 Zettler, 1991). Populations of the Indianmeal moth, the almond moth, and the red flour beetle collected from bulk peanuts and empty warehouses were also highly resistant to malathion (Arthur et al., 1988 Halliday et al., 1988). 

Both moth and plant are well adapted to their lifestyles. Because most yuccas produce little nectar, they offer no reward to attract other insects but entrust their pollination solely to yucca moths. The lack of nectar in yucca flowers means nothing to the moths. They have an incomplete gut and cannot feed in any event. Without nourishment, they live only long enough to fulfill their reproductive tasks. Two to four days after emerging from their cocoons, they die. 

It should be added that many other groups have contributed to the predevelopments of these inventions and also to later developments. All four reactions find wide application in organic synthesis. The Sharpless epoxidation of allylic alcohols finds industrial application in Arco s synthesis of glycidol, the epoxidation product of allyl alcohol, and Upjohn s synthesis of disparlure (Figure 14.4), a sex pheromone for the gypsy moth. The synthesis of disparlure starts with a Ci3 allylic alcohol in which, after asymmetric epoxidation, the alcohol is replaced by the other carbon chain. Perhaps today the Jacobsen method can be used directly on a suitable Ci9 alkene, although the steric differences between both ends of the molecules are extremely small ... 

A subset of all odorants is pheromones, about which much more follows later. Basically, pheromones transmit chemical messages among members of the same species. Bombykol is a pheromone for the silkworm moth the scent of lilacs as perceived by a human being is not. Although the question of human pheromones is difficult, that for many mammals is not. The pheromones in mammals are not detected... 

The sex pheromone of a New Zealand geometrid moth, the common forest looper, Pseudocoremia suavis Butler (Lepidoptera Geometri-dae), was identified as a mixture of four compounds. The two major active compounds were identified as (6Z)-c -9,10-epoxynonadec-6-ene and (3Z, 6Z)-c -9,10-epoxynonadeca-3,6-diene. Of the other two active compounds, one was identified tentatively as bZ, GZ)-cis-9,10-epoxyhenicosa-3,6-diene, the fourth however could not be identified due to insufficient amounts in the extract. 

Three PAG-active compounds were identified from the extracts of pheromone glands of the persimmon fruit moth, Stathmopoda masinissa Meyrick (Lepidoptera Oecophoridae). These were AE,6Z)-4,6-hexadecadienal and the corresponding acetate (EA,Z6- 6 OAc) and alcohol EA,Z6- 6 OY ). A preliminary field trail confirmed that the acetate as a single component attracted male moths, the possible roles of the aldehydes and the alcohol as components of lures remains to be determined. 

However, all levels of dietary pulegone affect the egg production of the moths. The data in Table VI Indicate a reduced oviposition rate even at the lowest (0.01%) pulegone concentration in the larval diet. The highest concentration (0.2%) reduces the egg production to 10% of that in the control moths and hatching is also reduced to 10% (13). 

Figures 3 and 4 indicate that the relations of composition and molecular size to the efficiency of petroleum oils against eggs of the citrus r mite are of the same type, with essentially the same critical values, as those foimd by Pearce, Chapman, and Frear (ff) for eggs of the oriental fruit moth. The ovicidal efficiency is nearly constant above a molecular weight of 340 and falls off very rapidly to indeterminate amounts below this level.

The density of antennal sensilla in males rises sharply away from the basal segment for about 1 cm then declines over the next 4 cm to the tip of the antenna (Schaller, 1978 Hosl, 1990). The two receptor cells that are tuned to each of the two periplanones are housed within the same sensillum, the basiconic single-walled type , along with two other cells that respond to terpenes and alcohols (Boeckh and Ernst, 1987). However, unlike the highly specialized receptor cells of male moths, the periplanone-A and periplanone-B cells have overlapping response spectra to these two compounds. Also, it is not known how responsiveness of pheromone-sensitive sensilla to food odorants (terpenes and alcohols) affects behavior of the male cockroach. 

Hydroxydanaidal has been extracted from coremata (Krasnoff and Roelofs, 1989). Like the cabbage looper moth, the salt marsh caterpillar moth has a dual signaling system, but in the case of E. acrea both males and females are attracted, leading to aggregations. 

Figure 15.6 (a) an opal bracelet and (b) the iridescent colours of the Madagascan sunset moth. The... 

Figure 3.2 A. Possible biosynthetic pathways for producing the sex pheromone components Z9-14 OAc and Z9,E12-14 OAc in the almond moth. The Z9-14 CoA and Z9,E12-14 CoA derivatives are reduced and acetylated to make the acetate esters. B. The biosynthetic pathway as determined by deuterium labeling studies presented in Figure 3.3.

Interestingly, chain shortening has been implicated in the alteration of pheromone ratios in several other species. In a laboratory selection pressure experiment using the RBLR moth, the Z/E ratio of ll-14 OAc could not be changed much from a 92/8 ratio (Roelofs et al., 1986). However, it was found that the ratio of E9-12 OAc/Ell-14 OAc could be selected and changed (Sreng et al., 1989). Two lines were selected, one with a low ratio of about 14 percent and one with... 

Therefore, although the desaturation and chain-shortening steps occur in a wide variety of moths, the order in which they occur and the type of desaturase must still be determined experimentally. 

Berg B. G., Galizia C. G., Brandt R. and Mustaparta H. (2002) Digital atlases of the antennal lobe in two species of tobacco budworm moths, the Oriental Helicoverpa assulta (male) and the American Heliothis virescens (male and female). J. Comp. 

Gibb, A.R., Comeskey, D., Bemdt, L., Brockerhoff, E.G., El-Sayed, A.M., Jactel, H. and Suckling, D. M. (2006). Identification of sex pheromone components of a New Zealand geometrid moth, the common forest looper Pseudocoremia suavis, reveals a possible species complex. J. Chem. Ecol., 32, 865-879. 

Tertiary pheromonal blends have been identified in two noctuid moths. The red bollworm, Diparopsis castanea, emits dodecyl acetate, (E)-9-dodecenyl acetate, 11-dodecenyl acetate, and (E)-9,ll-dodecadienyl acetate as a sex pheromone, whereas Spodoptera littoral is utilizes a blend made up of tetradecyl acetate, (E)-9-tetradecenyl acetate, (E)-ll-tetradecenyl acetate, and (Z,E)-9,ll-tetradecadieny1 acetate (89). For both species, the conjugated dienes are the most potent olfactory stimulants. 

Performing the reaction with uniformly labeled hexadecanoic acid and separating the isolated tetradecanoic acids also demonstrated the introduction of the 11-12 double bond. Conversion of the unsaturated products into epoxides followed by GLC separation showed radioactivity in both the saturated and unsaturated acids. Similar to the results discussed above with RBLR, a closely related insect, the Z E ratio of unsaturated acyl compounds was not the same as that in the pheromone. With the orange tortrix moth, the Z E ratio of unsaturated acids was ca. 2 1, whereas the pheromone was found to be all Z. 

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