Moth, gypsy

Functional group transformations of epoxides rank among the fundamental reactions of organic chemistry and epoxides are commonplace natural products The female gypsy moth for example attracts the male by emittmg an epoxide known as disparlure On detechng the presence of this pheromone the male follows the scent to its ongm and mates with the female... 

Many naturally occurring substances are epoxides You have seen two examples of such compounds already m disparlure the sex attractant of the gypsy moth (Section 6 18) and m the carcinogenic epoxydiol formed from benzo[a]pyrene (Section 118) In most cases epoxides are biosynthesized by the enzyme catalyzed transfer of one of the oxy gen atoms of an O2 molecule to an alkene Because only one of the atoms of O2 is trans ferred to the substrate the enzymes that catalyze such transfers are classified as monooxy genases A biological reducing agent usually the coenzyme NADH (Section 15 11) is required as well... 

Tetrahydrofurfuryl alcohol is a solvent and coupling agent for a phosphate-type insecticide used to control the gypsy moth. Esters of tetrahydrofurfuryl alcohol are used in preparations employed as insect repeUents. Tetrahydrofurfuryl alcohol is also used as a solvent—carrier for an EPA-approved paper sHmicide formulation. In this appHcation, the exceptional solvent action of tetrahydrofurfuryl alcohol prevents separation of the... 

Tree Preservation gypsy moths, caterpillars, borers, leaf miners, mites wounds from pmning or other damage to bark... 

Muscalure 20, the pheromone of the housefly has been prepared from oleic acid or erucic acid, similarly (Z)-l 1-heneicosene 21, the synergist of muscalure was obtained [189]. The intermediate 22 for the pheromone of the Cabbage looper was prepared using (Z)-methyl-4-octenedioate [166bJ, that was obtained by partial ozonolysis of (Z,Z)-l,5-cyclooctadiene. Similarly disparlure 23, the sex attractant of the gypsy moth, has been synthesized by two successive crossed-couplings with (Z)-4-octene dioate [191],... 

However, not all natural enemies are fully effective. For example, the gypsy moth has approximately 100 parasites and predators attacking it but the pest reaches outbreak levels periodically (35). Nearly 40 biological control agents were introduced from Europe and Asia to control the moth and 11 of these became established (44). Yet not one of the 11 blocontrol agents is providing fully effective control, although each contributes to some limitation of this pest. 

This is the first example of a reaction for which the presence of a chelating ligand was observed to facilitate rather than retard metal-catalysed epoxidation (Gao et al., 1987). It was found that the use of molecular sieves greatly improves this process by removing minute amounts of water present in the reaction medium. Water was found to deactivate the catalyst. All these developments led to an improved catalytic version that allows a five-fold increased substrate concentration relative to the stoichiometric method. Sensitive water-soluble, optically active glycidols can be prepared in an efficient manner by an in situ derivatisation. This epoxidation method appears to be competitive with enzyme-catalysed processes and was applied in 1981 for the commercial production of the gypsy moth pheromone, (-1-) disparlure, used for insect control (Eqn. (25)). 

The substrate-controlled addition of 18 to 19 proceeded with good enantioselec-tivity and was used to prepare the epoxide (+)-dispalure, a gypsy moth pheromone.184... 

Show how organoborane intermediates can be used to synthesize the gypsy moth pheromone E, Z-CH3C02(CH2)4CH=CH(CH2)2CH=CH(CH2)3CH3 from hept-6-ynyl acetate, allyl bromide, and 1-hexyne. 

The use of plant extracts for insect control dates into antiquity the use of Paris green as an insecticide for control of the Colorado potato beetle in 1867 probably marks the beginning of the modern era of chemical control of injurious insects. The development of lead arsenate followed later in the nineteenth century for gypsy moth control. The commercial production of nicotine insecticides, the production of calcium arsenate at the time of the first world war, and the use of fluorine, arsenical, and cyanide compounds, as well as other inorganic chemicals for insect control, were important steps in pest control. These chemicals were applied largely by dilute high pressure sprays or dusts. 

R,8S)-(+)-Disparlure (12) is the female sex pheromone of the gypsy moth (Lymantria dispar). Advent of Sharpless asymmetric dihydroxylation (AD) allowed several new syntheses of 12 possible. Sharpless synthesized 12 as shown in Scheme 17 [27]. Scheme 18 summarizes Ko s synthesis of 12 employing AD-mix-a [28]. He extended the carbon chain of A by Payne rearrangement followed by alkylation of an alkynide anion with the resulting epoxide to give B. Keinan developed another AD-based synthesis of 12 as shown in Scheme 19 [29]. Mit-sunobu inversion of A to give B was the key step, and the diol C could be purified by recrystallization. 

Forest Lymantria dispar (gypsy moth) Me2,epo7-18 H (disparlure) USA 10,000 150,000... 

A study using the gypsy moth, Lymantria dispar, illustrates the overall pathways involved in production of epoxide pheromone components (Fig. 3) [77]. This insect uses disparlure, Me2,epo7-18 H, as a pheromone component. In-... 

Commercial synthesis of the gypsy moth pheromone (7R,SS)-d sparlure by J. T. Baker ... 

Based on the tendency for higher levels of phenolics in organically grown plants, these are potentially less susceptible to pests and diseases. Indeed, Schultz and Baldwin (1982) and Rossiter et al., (1986) observed that high phenolic contents reduced the size of female gypsy moth pupae, leading to a decline in reproductive production of female gypsy moths. 

Rossister M, Schultz J C and Baldwin I T (1986), Relationships among defoliation, red oak phenolics, and gypsy moth growth and reproduction , Ecology, 69, 267-277. 

Schultz J C and Baldwin IT (1982), Oak leaf quality declines in response to defoliation by gypsy moth larvae , Science, 217, 149-50. 

Copper is toxic to sensitive species of terrestrial vegetation at >40 pg/L nutrient solution (seedlings of pines, Pirns spp.), at >10 mg/kg DW leaves (cucumber, Cucumis sativus), and >60 mg extractable Cu/kg DW soil (sweet orange, Citrus sinensis Table 3.4). Among sensitive species of terrestrial invertebrates, adverse effects on survival, growth, or reproduction occur at 2 pg Cu/cm2 on paper discs (earthworms), >50 mg Cu/kg diet (larvae of gypsy moth, Lymantria dispar), and 53 to 70 mg Cu/kg DW soil (earthworms and soil nematodes Table 3.4). 

Gypsy moth, Lymantria dispar Larvae were fed diets containing 10, 50, 250, or 1250 mg Cu/kg ration from first instar to pupation effects measured on development rate, growth, survival, and reproductive success Oribatid mite, Platynothrus peltifer Fed diets with 13 (control), 28, 64, 168, 598, or 1498 mg Cu/kg DW diet for 3 months... 

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 ... 

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