Recognition of foreign oviposition-marking pheromone in a multi-trophic context.

Both phytophagous and parasitic insects deposit oviposition-marking pheromones (OMPs) following oviposition that function to inform conspecifics of a previously utilized host of reduced suitability. The blueberry maggot fly, Rhagoletis mendax Curran (Diptera: Tephritidae), deposits eggs individually into blueberries and then marks the fruit surface with an OMP which reduces acceptance of fruit for oviposition by conspecifics. Diachasma alloeum (Muesebeck) (Hymenoptera: Braconidae) is a parasitic wasp attacking larval R. mendax which also deposits an OMP, signaling conspecifics of a wasp-occupied host. Behavioral studies were conducted testing the hypothesis that the OMP of the parasitic wasp modifies the oviposition behavior of its host fly. In this study, we show that the OMP of D. alloeum is recognized by R. mendax, and female flies will reject wasp-marked fruit for oviposition. Thus, we present a rare demonstration of pheromonal recognition between animals occupying different taxonomic orders and trophic levels. This chemical eavesdropping may enhance the ability of the fly to avoid fruit unsuitable for larval development.

Behavioral response of Lygus hesperus to conspecifics and headspace volatiles of alfalfa in a Y-tube olfactometer.

The western tarnished plant bug, Lygus hesperus Knight, feeds and develops on a variety of weeds in the spring, with later generations moving to alfalfa and cotton where severe damage to reproductive structures can occur. A synthetic attractant for monitoring or mass-trapping L. hesperus, or the identification of potential attractants for natural enemies, would be useful tools for integrated pest management programs. Studies investigated the response of naive and experienced fifth-instar and adult L. hesperus to odors associated with conspecifics and alfalfa, Medicago sativa L. Fifth-instar L. hesperus responded to all plant/insect combinations, whereas female L. hesperus only responded preferentially to vegetative and flowering alfalfa where conspecifics had fed for 24-72 hr, and to vegetative alfalfa where conspecifics were added approximately 30 min before the test began. Males were not attracted to headspace volatiles from any of the alfalfa treatments. Analysis of headspace volatiles showed that (E)-2-hexanal, (Z)-3-hexen-l-ol, alpha-pinene, (Z)-3-hexenyl acetate, (E)-2-hexenyl acetate, limonene, (Z)-ocimene, (E)-beta-ocimene, linalool, (3E)-4,8-dimethyl-1,3,7-nonatriene, and (E, E)-alpha-farnesene are emitted from both vegetative and flowering alfalfa. Indole and (3E, 7E)-4,8,12-trimethyl-1,3,7,11-tridecatetraene were only detected in flowering alfalfa. Damage to alfalfa by L. hesperus increased emissions of (Z)-ocimene, (E)-beta-ocimene, (E)-beta-caryophyllene, and (E, E)-alpha-farnesene, while beta-pinene, myrcene, methyl salicylate, and (3E, 7E)-4,8,12-trimethyl-1,3,7,11-tridecatetraene were only detected from damaged plants. Thus, individual or mixtures of these alfalfa volatiles may be useful as attractants for capturing nymphs and adult females of L. hesperus in the field.

Exogenous methyl jasmonate induces volatile emissions in cotton plants.

We investigated the effect of exogenous methyl jasmonate (MeJA) on the emission of herbivore-induced volatiles; these volatile chemicals can signal natural enemies of the herbivore to the damaged plant. Exogenous treatment of cotton cv. Deltapine 5415 plants with MeJA induced the emission of the same volatile compounds as observed for herbivore-damaged plants. Cotton plants treated with MeJA emitted elevated levels of the terpenes (E)-beta-ocimene, linalool, (3E)-4,8-dimethyl-1,3,7-nonatriene, (E,E)-alpha-farnesene, (E)-beta-farnesene, and (E,E)-4,8,12-trimethyl-1,3,7,11-tridecatetraene compared to untreated controls. Other induced components included (Z)-3-hexenyl acetate, methyl salicylate, and indole. Methyl jasmonate treatment did not cause the release of any of the stored terpenes such as alpha-pinene, beta-pinene, alpha-humulene, and (E)-beta-caryophyllene. In contrast, these compounds were emitted in relatively large amounts from cotton due to physical disruption of glands by the herbivores. The timing of volatile release from plants treated with MeJA or herbivores followed a diurnal pattern, with maximal volatile release during the middle of the photoperiod. Similar to herbivore-treated plants, MeJA treatment led to the systemic induction of (Z)-3-hexenyl acetate, (E)-beta-ocimene, linalool, (3E)-4,8-dimethyl-1,3,7-nonatriene, (E,E)-alpha-farnesene, (E)-beta-farnesene, and (E,E)-4,8,12-trimethyl-1,3,7,11-tridecatetraene. Our results indicate that treatment of cotton with MeJA can directly and systemically induce the emission of volatiles that may serve as odor cues in the host-search behavior of natural enemies.

Avocadofurans and their tetrahydrofuran analogues: comparison of growth inhibitory and insecticidal activity.

The importance of the double bonds in the furan ring of avocadofurans with relation to their insecticidal activity was examined. The insecticidal activity of two naturally occurring avocadofurans, 2-(pentadecyl)furan and 2-(heptadecyl)furan, was compared to the toxicity of five tetrahydrofurans with alkyl chains at position 2 and varying side chains from 14 to 18 carbons. We found that eliminating the sites of unsaturation in the furan ring of avocadofurans significantly reduced the detrimental effects on the mortality and growth of the generalist insect herbivore Spodoptera exigua. In 7-day bioassays, S. exigua larvae were significantly more affected when fed a diet containing avocadofurans as compared to a larvae fed diet treated with the analogous tetrahydrofurans. Although larvae fed with the tetrahydrofurans showed reduced growth as compared to controls, larval mortality was not significantly increased. We conclude that the double bonds in the furan ring of avocadofurans play an important role in their insecticidal effects.

Alkylfurans: effects of alkyl side-chain length on insecticidal activity.

The insecticidal activity of five alkylfurans against the generalist insect herbivore beet armyworm, Spodoptera exigua, was examined. Two naturally occurring compounds, the avocadofurans 2-(pentadecyl)furan (1) and 2-(heptadecyl)furan (2), previously isolated from specialized avocado idioblast oil cells, and three homologues, 2-(tetradecyl)furan (3), 2-(hexadecyl)furan (4), and 2-(octadecyl)furan (5), were synthesized. Bioassays of alkylfurans 1-5 using a 9-day diet-incorporation initiated with neonates showed that all alkylfurans tested significantly increased S. exigua larval mortality and reduced larval weights, with maximal biological activity detected among the naturally occurring alkylfurans 1 and 2.

Isolation, identification, and biological activity of isopersin, a new compound from avocado idioblast oil cells

A new compound, (12Z,15Z)-1-hydroxy-4-oxo-heneicosa-12,15-dien-2-yl acetate, isopersin (2), has been isolated from avocado idioblast oil cells. In artificial diet bioassays, 2 showed no effects on either larval survivorship or growth of early-instar beet armyworm Spodoptera exigua. In contrast, the isomeric persin (1), (12Z, 15Z)-1-acetoxy-2-hydroxy-4-oxo-heneicosa-12,15-diene, reduces larval growth at equivalent concentrations (500 &mgr;g g-1). Compound 2 is not very stable and isomerizes readily to 1. Both compounds are acid-labile, rearranging rapidly to alkylfuran 3 in the presence of traces of acid.