Cockroach

Much of the communication between insects involves chemical messengers called pheromones A species of cockroach secretes a substance from its mandibular glands that alerts other cockroaches to its presence and causes them to congregate One of the principal components of this aggregation pheromone is the alkane shown in the bond line formula that follows Give the molecular formula of this substance and represent it by a condensed formula... 

White phosphorus, iacorporated ia sweet syrup, forms a useful bait for cockroaches. SiUcic acid, Si02 or H2Si02, very finely divided, is a rapidly acting desiccant that kills cockroaches, fleas, termites, and stored-grain pests by dehydration. 

Methoprene and hydroprene are first-generation juvenoids that iacorporate minor stmctural optimisation of neotenin to increase persistence. Methoprene, 1-isopropyl (E,E)-ll-methoxy-3,7,ll-tnmethyl dodecadi-2,4-enoate (129) (bp 100 C/6.7 Pa, vp 3.5 mPa at 25°C), is soluble ia water to 1.4 mg/L. The rat oral LD q is >34,000 mg/kg. Methoprene has been used as a mosquito larvicide, ia baits for ant control, and as a catde feed-through treatment for horn fly control. Hydroprene, methyl (H,H)-3,7,ll-trimethyl-dodecadi-2,4-enoate (130) (bp 174°C at 2.5 kPa, vp 2.5 mPa at 25°C), is soluble ia water to 0.54 mg/L. The rat oral LD q is >34,000 mg/kg. Hydroprene is especially effective against aphids and cockroaches. 

Second-generation juvenoids incorporate more substantial stmctural departures from neotenin and are more resistant to metaboHc and environmental degradation. Epiphenonane, 2-ethyl-3-[3-ethyl-5-(4-ethylphenoxy)-pent-3-en-yl] 2-methyloxirane (131), has a rat oral LD q of 4000 mg/kg. It and similar juvenoids are used in China and Japan to prolong the last larval instar of the silkworm so that silk production is increased 10—15%. Fenoxycarb, ethyl [2-(4-phenoxyphenoxy)ethyl] carbamate (132) (mp 53°C, vp 0.0078 mPa at 20°C), is soluble in water to 6 mg/L. The rat oral LD q is >16,800 mg/kg. Fenoxycarb has a wide spectmm of activity, interfering with the developmental processes of fleas, cockroaches, and ants. 

Hydramethylnon [67485-29-4] is tetrabydro-5,5-dimetbyl-2-(1 H)-pyrimidinone [bis-l,5-(4-trifluoromethylphenyl)-3-penta-l,4-dienylidene] hydrazone (152) (mp 189°C). It is a slow-acting stomach poison used in baits and traps to control ants and cockroaches. Its mode of action is inhibition of mitochondrial electron transport. 

Sulflutamid or A/-ethylpetfluotoctanesulfonamide [4151 -50-2] CgF yS02NHC2H, is a slow-acting stomach poison used in baits for the control of ants and cockroaches. It acts as an uncoupler of oxidative phosphorylation. 

The organophosphoms ester dichlorvos is sufficiently volatile to be incorporated either in permeable plastic bottles or plastic strips which permit its controlled release for fumigation of cupboards and closets to control cockroaches, or as flea collars on pets. 

Insecticides. The use of iodine-based compounds as insecticides is of minor importance. The active ingredient is lodofenphos (142). It is formulated to be used in pubHc health and animal husbandry, eg, for cockroach control (see Insectcontroltechnology). 

Encapsulated dia2innon sold as Knox-Out 2FM is a commercial encapsulated pesticide formulation said to have reduced dermal and oral toxicity as well as prolonged effectiveness. The capsules, prepared by interfacial polymeri2ation, are claimed to be highly effective against cockroaches with no objectionable odor and low insect repeUence. The capsules are beheved to function as a contact poison when insects walk on it and as a stomach poison when insects preen capsules stuck to their legs and ingest them (71). 

Indoor Pests cockroaches, fleas, flies, Hce, carpet beetles, clothes moths, silverfish, centipedes, millipedes, termites mice, rats mil dew... 

A listing of compounds evaluated in the laboratory as cockroach repeUents summarizes 872 synthetic compounds out of 901 bioassayed from 1953 to 1974 (43). EenchoHc acid [512-77-6] (3-isopropyl-1-methylcyclopentanecarboxyHc acid) has been used as a standard repeUent in tests conducted by placing 20 cockroaches in a glass crystallizing dish without food and water and offering them a choice of two cardboard shelters, one of which was treated with 1 or 2 mL of a 1% solution of the candidate in acetone. Counts were made daily for seven days. 

Sixty-two novel experimental carboxamides of 1,2,3,6-tetrahydropyridine have been tested as repellents of German cockroaches, and five provided 100% repeUency for 17 d in a stringent test (48). 

Eaboratory Evaluations of Compounds as Kepellents to Cockroaches, 1953—1974, Production Research Report No. 64, Agricultural Research Service,... 

Sulfoxides occur widely in small concentrations in plant and animal tissues, eg, aHyl vinyl sulfoxide [81898-53-5] in garlic oil and 2,2 -sulfinylbisethanol [3085-45-8] as fatty esters in the adrenal cortex (1,2). Homologous methyl sulfinyl alkyl isothiocyanates, which are represented by the formula CH3SO(CH2) NCS, where n = 3 [37791-20-1], 4 [4478-93-7], 5 [646-23-1], 8 [75272-81-0], 9 [39036-83-4], or 10 [39036-84-5], have been isolated from a number of mustard oils in which they occur as glucosides (3). Two methylsulfinyl amino acids have also been reported methionine sulfoxide [454-41-1] from cockroaches and the sulfoxide of i -methylcysteine, 3-(methylsulfinyl)alaiiine [4740-94-7]. The latter is the dominant sulfur-containing amino acid in turnips and may account in part for their characteristic odor (4). 

Schabe, /. scraper grater scab, itch cockroach moth. 

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. 

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