Methyl 2-(methylthio)benzoate: the unique sulfur-containing sex pheromone of Phyllophaga crinita

Robbins, Paul S.; Crocker, Robert; Nojima, Satoshi; Morris, Bret A.M.; Roelofs, Wendell L.; Villani, M. G.

doi:10.1007/s00114-003-0469-5

Cited by 26 publications

(17 citation statements)

References 18 publications

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“…The air stream carried the column effluent over the beetle antennal preparation. See Robbins et al (2003) for a photograph of the beetle antennal preparation. The output signal from the antenna was amplified by a customized single-step highinput impedance DC amplifier.…”

Section: Methodsmentioning

confidence: 99%

Experimental Evidence for Three Pheromone Races of the Scarab Beetle Phyllophaga anxia (LeConte)

et al. 2008

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This study offers experimental evidence for the existence of three pheromone races of the northern genitalic form of Phyllophaga anxia: one race in which females produce and males respond mainly to L-valine methyl ester, a second producing and responding to L-isoleucine methyl ester, and a third producing and responding to an intermediate range of blends of the two compounds. At Franklinville, NY, pheromone gland contents of females were analyzed using coupled gas chromatography-electroantennogram detection. Two types of females were found, one that produced greater than 99% L-valine methyl ester and another that produced greater than 99% Lisoleucine methyl ester. Capture-mark-release-recapture field tests with males at Franklinville established that most males were recaptured in traps baited with the same blends with which they were originally captured. The populations characterized at Franklinville, NY, have also been found at numerous locations from eastern Canada and the northeast and north central USA, sometimes in allopatry and sometimes in sympatry. At a site in Carver, MA, P. anxia males responded to blends of the methyl esters of L-valine and L-isoleucine, and Carver females produced blends similar to those to which the males responded. Populations responding to blends have been identified only from southeastern Massachusetts and Rhode Island. At a field site near Waterloo, NY, the addition of small proportions of L-isoleucine methyl ester to lures containing L-valine methyl ester did not affect trap captures, but higher proportions of L-isoleucine methyl ester were inhibitory, decreasing trap captures.

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Section: Methodsmentioning

confidence: 99%

Experimental Evidence for Three Pheromone Races of the Scarab Beetle Phyllophaga anxia (LeConte)

et al. 2008

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“…In fact, insect use of sulfur-containing semiochemicals has been found in only a few species. Robbins et al (2003) reported methyl 2-(methylthio)benzoate as a unique sulfurcontaining sex pheromone for a scarab beetle, Phyllophaga crinita. Sulfur-containing components of the sex pheromone of the cockroach Nauphoeta cinerea are 2-methylthiazolidine and 2-methyl-2-thiazoline (Sreng 1990;Sirugue et al 1992).…”

Section: Discussionmentioning

confidence: 99%

Earwigs (Labidura riparia) mimic rotting-flesh odor to deceive vertebrate predators

Byers

2015

Sci Nat

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Many insects repel predators with caustic chemicals, while insects mimicking odors of wastes/dead insects to fool predators have not been documented. We found that the shore earwig, Labidura riparia (Dermaptera: Labiduridae) when bitten by anole lizards, Anolis carolinenesus, spits a rotting-flesh odor that deceives these insectivores into rejecting prey. Once a lizard attacked and rejected an earwig, the lizard did not attack another earwig during several weeks despite consuming other prey, indicating associative learning after one trial. The fetid odor was found in the head-prothorax containing salivary glands of both male and female earwigs and was comprised of ∼ 100 ng dimethyl disulfide and ∼ 600 ng dimethyl trisulfide. Nymphs had <5 ng of either compound. Adults also spit odorous sulfides after prolonged attacks by harvester ants, Pogonomyrmex rugosus, who were only deterred by the earwig's forceps. Sulfides released by the earwig are similar to odors of carrion/feces, which may be innately repulsive to some vertebrate predators. The mean initial discharge percentage (IDP) of sulfides from a cohort of earwigs was 62 %; however, IDPs of individuals were highly variable (3-99 %; mean 57 %). The discharge refill time (DRT) to refill 50 % of the earwig's allomone reservoir was estimated at 13 h. A positive relationship in sulfide amounts with body weight was found only in females in 2009, suggesting metabolic cost tradeoffs were revealed when sulfide content was half that in 2010. This is the first report of insects releasing sulfur-containing compounds that may mimic carrion-fecal odors as a deceptive defense against vertebrate predators.

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“…The sex pheromone of Phyllophaga crinita was identified as methyl 2-(methylthio)benzoate (Robbins et al 2003). Interestingly, Coca-Abia (2002) has recently resurrected the genus Trichesthes and removed P.…”

Section: Discussionmentioning

confidence: 99%

TrappingPhyllophagaspp. (Coleoptera: Scarabaeidae: Melolonthinae) in the United States and Canada using sex attractants

Robbins¹,

Alm²,

Armstrong³

et al. 2006

Journal of Insect Science

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The sex pheromone of the scarab beetle, Phyllophaga anxia, is a blend of the methyl esters of two amino acids, L-valine and L-isoleucine. A field trapping study was conducted, deploying different blends of the two compounds at 59 locations in the United States and Canada. More than 57,000 males of 61 Phyllophaga species (Coleoptera: Scarabaeidae: Melolonthinae) were captured and identified. Three major findings included: (1) widespread use of the two compounds [of the 147 Phyllophaga (sensu stricto) species found in the United States and Canada, males of nearly 40% were captured]; (2) in most species intraspecific male response to the pheromone blends was stable between years and over geography; and (3) an unusual pheromone polymorphism was described from P. anxia. Populations at some locations were captured with L-valine methyl ester alone, whereas populations at other locations were captured with L-isoleucine methyl ester alone. At additional locations, the L-valine methyl ester-responding populations and the L-isoleucine methyl ester-responding populations were both present, producing a bimodal capture curve. In southeastern Massachusetts and in Rhode Island, in the United States, P. anxia males were captured with blends of L-valine methyl ester and L-isoleucine methyl ester.

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Methyl 2-(methylthio)benzoate: the unique sulfur-containing sex pheromone of Phyllophaga crinita

Cited by 26 publications

References 18 publications

Experimental Evidence for Three Pheromone Races of the Scarab Beetle Phyllophaga anxia (LeConte)

Experimental Evidence for Three Pheromone Races of the Scarab Beetle Phyllophaga anxia (LeConte)

Earwigs (Labidura riparia) mimic rotting-flesh odor to deceive vertebrate predators

TrappingPhyllophagaspp. (Coleoptera: Scarabaeidae: Melolonthinae) in the United States and Canada using sex attractants

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