Stink bug

Isopropyl-4,6-dimethyltricyclo[4.4.05 9]dec-3-en-2-one (40) with unknown absolute configuration was isolated as a putative male pheromone of a Brazilian predatory stink bug (Tynacantha marginata), and its enantiomers were synthesized by Kuwahara as shown in Scheme 58 [88]. The triene A gave B and C by an intramolecular Diels-Alder reaction, and they could be converted to the enantiomers of 40. 

Cotton pests that are common both to the United States and tropical America include the cotton aphid (Aphis gossypii Glov.), the cotton leafworm [Alabama argillacea (Hbn.)], and certain grasshoppers and spider mites. Certain species of stink bugs, mirids, and cutworms which are closely related to species that occur here at times cause serious injury to cotton throughout Mexico and Central and South America. 

Aposematic species from two different families produce pungent pyrazines, presumably as an additional warning to potential predators of their toxicity. These include Oncopeltus fasciatus (Lygaeidae, seed bug family) that secretes 2-isobutyl-3-methoxypyrazine [28], and the stink bug Murgantia histrionica (Pentatomidae), that oozes froth containing 2-isobutyl- and 2-sec-butyl-3-methoxypyrazine when molested [39]. 

Scheme 6 Synthesis of the racemate of a novel tricyclic sequiterpenoid produced by males of the stink bug Tynacantha marginata [65]...

Scheme 8 Syntheses of cis-Z- and Jrans-Z-bisabolene epoxide pheromone components from Nezara viridula and other stink bug species, part 1 [67,71,76,77]...

Scheme 25 Synthesis of (Z)-exo-a-bergamotenal, isolated from male Eysarcorisparvus stink bugs [114]...

Stink bugs (Heteroptera, Pentatomidae) for example are well known for the odorous volatile secretion they emit from their metathoracic glands when molested [175]. 

Predaceous Stink bugs Medical shield shape Feed on many insects... 

Extract of odors collected from sexually mature males of the green stink bug, Acrostemum hilare Ssy (Hemiptera Pentatomidae), showed one major sex-specific component, (45)- r-(Z )-bisabolene epoxide [(45)-cis-2 -BAE]. The crude extract was attractive to females, but when separated into four fractions, only the portion containing (45)-c -2 -BAE and the minor component AS)-trans-Z- AE was attractive to females. The fraction was as attractive as the crude extract suggesting that the former contained all the components. Neither the cis- nor the trans- BAE alone was attractive to females, but a 95 5 cis-.trans blend, mimicking the ratio naturally produced by males was attractive to females in Y-tube bioassays. " ... 

The male produced sex pheromone of the red-shouldered stink bug, Thyantapallidovirens Stal (Hemiptera Pentatomidae), was shown to consist of a blend of methyl ( "2, Z 4,. Z6)-decatrienoate and the sesquiterpenes (+)-a-curcumene, (—)-zingiberene and (—)-P-sesquiphellandrene. In laboratory bioassays, sexually mature males attracted sexually mature females but not males, and females did not attract either sex. Pheromone... 

Two male specific compounds were identified as the sex ph eromones of the Brazilian rice stalk stink bug, Tibraca limbativentris Stal (Hemiptera Pentatomidade), as isomers of (k5)-zingiberenol. ... 

Volatiles collected from the male red-shouldered stink bug, Thyanta perditor, attracted females. The major component was identified as a male-specific compound, methyl (2E, AZ, 6.Z)-decatrienoate. ... 

Male-produced sex pheromones of the Brazilian soybean stink bugs, Euschistus heros and Piezodorous guildinli, are methyl-2,6,10-trimethyltridecanoate and methyl-2,6,10-trimethyldodeacanoate respectively. These two compounds were synthesized as a mixture of stereoisomers. Another synthesis for the sex pheromone of the male stink bug Euschistus heros, along with the synthesis of the pheromone of the rice moth, Corcyra cephalonica, has been reported. 

Synthetic studies aimed to elucidate the stereostructure of the aggregation pheromone of the male stink bug Erysarcoris lewisi, which is 2-methyl-6-(4 -methylenebicyclo [3 1 0] hexyl)hept-2-en-l-ol was reported. ... 

Identification of three male-produced sex pheromones of the stink bugs Chlorochroa ligata and C. uhleri, which are methyl R)-3- E)-6-2,... 

Daidzin and genistin (isoflavones) Stink bug Nezara viridula) 377... 

Millar, J. G., Rice, R. E., Steffan, S. A., Daane, . M., Cullen, E. and Zalom, F. G. (2001). Attraction of female digger wasps, Astata occidentalis Cresson (Hymenoptera Sphecidae) to the sex pheromone of the stink bug Thyanta pallidovirens (Hemiptera Pentatomidae). Pan-Pacific Entomologist 77 244-248. 

Of the best-known insect orders, only the Hemiptera, the true bugs, stand out as a group without a clearly recognized JH. An early report identified JH I as the principal hormone in the hemolymph of the adult female bean beetle, Riptortus clavatus (Hemiptera Alydidae) by gas chromatography—MS (GC—MS).78 It was reported that, of the three compounds JH I, II, and III, JH I was the most effective for inducing yolk protein synthesis in diapausing adults of this species.78 More recently, it has been reported that a compound close to JH III, but not JH III, is the hormone in the two spotted stink bug Perillus bioculatus (Hemiptera Pentatomidae). Production of this hormone is stimulated by farnesol, a known precursor of JH III.79... 

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