Porthetria dispar

Data are limited on nickel concentrations in terrestrial invertebrates. Earthworms from uncontaminated soils may contain as much as 38 mg Ni/kg DW, and workers of certain termite species may normally contain as much as 5000 mg Ni/kg DW (Table 6.6). Larvae of the gypsy moth (Porthetria dispar) near a nickel smelter had 20.4 mg Ni/kg DW concentrations in pupae and adults were lower because these stages have higher nickel elimination rates than larvae (Bagatto et al. 1996). 

Gypsy moth, Porthetria dispar, near ore smelter at Sudbury, Ontario, Canada vs. reference site ... 

Z)-7,8-epoxy-2-methyl-octade cane [29804-22-6] CH3(CH2)9CH —CH(CH2)4CH(CH3)2 0 gypsy moth, Porthetria dispar... 

Females of the lymantriid, Porthetria dispar, the gypsy moth, liberate cls-7,8-epoxy-2-methyloctadecane (disparlure) as a sex pheromone (78). The probable precursor of the epoxide, (Z)-2-methyl-7-octadecene, is present in the gland in large quantities, and it has been demonstrated that the olefin is epoxidized in vivo (79). Disparlure is rapidly adsorbed on the male antennae and quickly converted to two more polar metabolites (80), probably as a consequence of hydrolysis of the epoxide group. 

The utility of this new procedure has been demonstrated by the synthesis of mus-calure, the sex pheromone of the house fly Musca domestica) (Eq. 68)I22) and dis-parlure, the sex pheromone of the Gypsy moth (Porthetria dispar L.)123), and the sex attractant of soybean loopers (Pseudoplusia includens)124>. 

Volatility of the attractant molecule is an important consideration. The effectiveness of some lures over great distances implies an appreciable degree of volatility, a property that is, in part, tied to the size of the molecule. At first we believed that a compound with 11 or 12 carbon atoms was about the optimum size and this idea seemed to work with some of the fruit fly lures. A compound of this size is volatile enough to be detected but not so volatile that it would last only a short time. The finding of gyplure, the synthetic sex attractant of the gypsy moth [Porthetria dispar (L.)l, which has 20 carbon atoms... 

Epoxide ring opening of 484c with -nonylmagnesium bromide in the presence of copper(I) bromide provides in 77% yield the alcohol 489, which is transformed into (+ )-(77 ,8 S)-disparlure (490), the sex pheromone of the gypsy moth Porthetria dispar [159]. 

The structure of the major attractant of the gypsy moth, Porthetria dispar has been shown to be (-l-)10-acetoxy-cis-7-hexadecen-l-ol (CXXVIII)... 

Other, sex-attractant, pheromones are secreted by the female. That from the silkworm moth is hexadeca-10-/rflm -12-m-dien-l-ol, that from the gipsy moth (Porthetria dispar) is aV-7,8-epoxy-2-methyloctadecane and the attractant released by the female bollworm moth is 10-propyl-5,9-tridecanol. 

Bestmann, H. J., and O. Vostrowsky Pheromone. III. Eine stereoselektive Synthese von 7,8-Z-Epoxy-2-methyloctadecan, dem Sexuallockstoff des Schwammspinners (Lymantria dispar, Porthetria dispar, Lepidoptera). Tetrahedron Lett. 1974, 207—208. 

Eiter, K. Novel total synthesis of sex attractant of Porthetria dispar (7,8-cw-epoxy-2-methyloctadecane). Angew. Chem. Int. Ed. Engl. 11, 60—61 (1972). 

Kovalev, B. G., R. I. Ishchenko, and V. A. Marchenko (Synthetic studies on sexual attractants of insects. I. Synthesis of 2-methyl-7-octadecene oxide (disparlure) as a sexual attractant of an unpaired silkworm Porthetria dispar.) Zh. Org. Khim. 9, 6—8 (1973). 

Mori, K., T. Takigawa, and M. Matsui Stereoselective synthesis of optically active disparlure, the pheromone of the gypsy moth (Porthetria dispar L.j. Tetrahedron Lett. 1976, 3953—3956. 

Tolstikov, G. A., V. N. Odinokov, R. I. Galeeva, and R. S. Bakeeva New stereoselective synthesis of racemic disparlure, sex pheromone of the gypsy moth (Porthetria dispar L.). Tetrahedron Letters 1978, 1857—1858. 

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