Houseflies

Female houseflies attract males by sending a chemical signal... 

The sex attractant by which the female housefly attracts the male has the molecular formula C23H46 Catalytic hydrogenation yields an alkane of molecular formula C23H4g Ozonolysis yields... 

Baits include mixtures of toxicant, usually at l ndash 5%, with a carrier especially attractive to the insect pest. Carriers include sugar for the houseflies, protein hydrolysates for fmit flies, bran for grasshoppers, and honey, chocolate, or peanut butter for ants. 

Diphenylamine has shown activity against the body louse, chiggers, housefly, and, as the chloro derivative, against the red spider mite. Diarylamines have also been reported to have antiradiation activity (48). 

Z)-9-Tricosene [(Z)-CH3(CH2)7CH=CH(CH2)i2CH3] is the sex pheromone of the female housefly. Synthetic (Z)-9-tricosene is used as bait to lure male flies to traps that contain insecticide. Using acetylene and alcohols of your choice as starting materials, along with any necessary inorganic reagents, show how you could prepare (Z)-9-tricosene. 

The sex attractant of the common housefly is a hydrocarbon with the formula C23H46. On treatment with aqueous acidic KMn04, two products are obtained, CH3(CH2),2C02H and Cb fCB hCX H. Propose a structure. 

The sex attractant given off by the common housefly is an alkene named muscahtre. Propose a synthesis of muscalure starting from acetylene and any alkyl halides needed. What is the IUPAC name for muscalure ... 

Housefly, sex attractant of, 255 HPLC, 432 Hiickel, Erich, 523 Htickel 4/j + 2 rule, 523... 

The edible parts of parsnips (Pastimea sativa L.), which have been consumed for centuries by humans without causing any obvious harm, were found to contain a chemical of insecticidal and strong synergistic nature (1). The insecticidal constituent, present at about 200 p.p.m., was isolated and identified as 5-allyl-l-methoxy-2, 3-methylenedioxybenzene or myristicin. Its toxicity to various insects [vinegar flies, houseflies, Mediterranean fruit flies, mosquito larvae, Mexican bean beetles, and pea aphids] was established and compared with pyrethrum and aldrin (Tables I and II). The knockdown effect, although definite, was not as great as that of pyrethrum. In tests... 

The wide distribution of this insecticide in other cruciferous crops was investigated later, and the stability and occurrence of this compound were studied. Two cabbage varieties, cauliflower, brussels sprouts, broccoli, kale, mustard, and kohlrabi contained 2-phenylethyl isothiocyanate in various amounts as evidenced by gas-liquid chromatography and bioassay (houseflies and vinegar flies) (Table VII). Insecticidal activities were encountered only with root tissues. Compounds of insecticidal activity, not attributable to 2-phenylethyl isothiocyanate, were found in the edible parts of radish and leaves of turnip, rutabaga, and garden cress. 

Jasmolin II in pure form was nearly equal to cinerin II in toxicity to houseflies but much less when synergized. The synergistic factor of the synergized compounds is pyrethrum extract 9.6 jasmolin II, 7.0 cinerin II, 12.0. 

Sawicki et al. (33) prepared by reconstitution pure samples of pyrethrins I and II and cinerins I and II and compared the toxicity of these esters with the regular pyrethrum extract on houseflies 5 to 6 days old. 

Sawicki and Elliott (31) re-examined the insecticidal activity of pyrethrin extracts and its four insecticidal constituents against four strains of houseflies, and checked the relative toxicity of pyrethrins I and II. This work confirmed the earlier results, showing that pyrethrin II was 1.3 to 1.6 times more toxic than pyrethrin I, but that the relative toxicities of pyrethrins I and II against the four strains of flies differed little. Resistance to knockdown but not to killing was associated in these strains with resistance to organophos-phorus and chlorinated insecticides. 

Bates, Hewlett, and Lloyd (I) found that both piperonyl butoxide and SKF 525A, the ester of 2-diethylaminoethyl 2,2-diphenyl-w-pentanoate, synergized the action of pyrethrins on insects of species of the lesser mealworm beetles and houseflies but both antagonized the action of malathion. SKF 525A is known to increase the effects on mammals of drugs of various types and has been shown to synergize pyrethrins. 

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],... 

Ascher and Nemny 495) found that residues of triphenyltin acetate on glass, resulting from the evaporation of acetone solutions thereof, were, on contact to houseflies, less toxic with rising concentration. As triphenyltin acetate is likely to be a self-associated polymer in the solid state [similar to trimethyltin acetate (355)] and in concentrated solutions, it was suggested 495) that the monomer, which exists in dilute solutions, is toxic to insects, and the polymer, nontoxic. Interestingly, in this connection, a triphenyltin methacrylate copolymer has 470) a very low mammalian toxicity (acute, oral LDso for mice >2000 mg/kg). 

CYP6D1 of the housefly (Musca domestica) has been found to hydroxylate cyper-methrin and thereby provide a resistance mechanism to this compound and other pyrethroids in this species (Scott et al. 1998 see also Chapter 12). Also, this insect P450 can metabolize plant toxins such as the linear furanocoumarins xanthotoxin and bergapten (Ma et al. 1994). This metabolic capability has been found in the lepi-dopteran Papilio polyxenes (black swallowtail), a species that feeds almost exclusively on plants containing furanocoumarins. 

Mechanism of action can be an important factor determining selectivity. In the extreme case, one group of organisms has a site of action that is not present in another group. Thus, most of the insecticides that are neurotoxic have very little phytotoxicity indeed, some of them (e.g., the OPs dimethoate, disyston, and demeton-5 -methyl) are good systemic insecticides. Most herbicides that act upon photosynthesis (e.g., triaz-ines and substituted ureas) have very low toxicity to animals (Table 2.7). The resistance of certain strains of insects to insecticides is due to their possessing a mutant form of the site of action, which is insensitive to the pesticide. Examples include certain strains of housefly with knockdown resistance (mutant form of Na+ channel that is insensitive to DDT and pyrethroids) and strains of several species of insects that are resistant to OPs because they have mutant forms of acetylcholinesterase. These... 

The organophosphorons insecticides dimethoate and diazinon are mnch more toxic to insects (e.g., housefly) than they are to the rat or other mammals. A major factor responsible for this is rapid detoxication of the active oxon forms of these insecticides by A-esterases of mammals. Insects in general appear to have no A-esterase activity or, at best, low A-esterase activity (some earlier stndies confnsed A-esterase activity with B-esterase activity) (Walker 1994b). Diazinon also shows marked selectivity between birds and mammals, which has been explained on the gronnds of rapid detoxication by A-esterase in mammals, an activity that is absent from the blood of most species of birds (see Section 23.23). The related OP insecticides pirimiphos methyl and pirimiphos ethyl show similar selectivity between birds and mammals. Pyrethroid insecticides are highly selective between insects and mammals, and this has been attributed to faster metabolic detoxication by mammals and greater sensitivity of target (Na+ channel) in insects. 

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