Acanthoscelides obtectus

Attractive Compounds. The male produced sex pheromone of the dried bean beetle, Acanthoscelides obtectus, is an unusual methyl ester, methyl (R,2 )-2,4,5-tetradecatrienoate 204 [372] (Scheme 23). The compound was among the first pheromones identified from male beetles, and only very recently other insect volatiles showing allenic structures have been described [184]. Careful head... 

Acanthoscelides obtectus, produce (-)-methyl (Ej-2,4,5-tetradecatrienoate, the only allenic sex pheromone identified in insects (49). Each beetle produces 10-20 M9. of this compound, which may be accompanied by a closely-related ester, possibly methyl (E)-2,4,6-tetradecatrienoate. The role of this compound as a sex pheromone has not been unambiguously established. 

Regnault Roger, C. and Hamraoui, A. (1995) Comparison of the insecticidal effects of water extracted and intact aromatic plants on Acanthoscelides obtectus, a bruchid beetle pest of kidney beans. Chemoecology 5(6), 1-5. 

Eggs on grain Pulses (whole) Acanthoscelides obtectus,... 

Lavender Lavendula spp. linalool Acanthoscelides obtectus Cydia pomonella [12-13]... 

Beetle, Japanese Popillia japonica) Beetle, lady Ceratomegilla fuscilabrus) Mealworm, yellow (Tenebrio nwlitor) Weevil, bean (Acanthoscelides obtectus) (196-276) (83-180) (176-222) m 114 f 146 13.1 m(2.9-6.8) f(2.8-8.3)... 

The racemic allenic ester (148), produced by the male Dried Bean Beetle Acanthoscelides obtectus (Say), has been synthesized from the allenic alcohol (149). Attempted bromination of (149) with PBrs led to very poor yields of the bromide (150) whereas a CBr4-PPh3 mixture give high yields under very mild conditions (see Scheme 38). Roumestant, in his continuing series of studies on the... 

Golgbiowski, M. Malihski, E. Nawrot, J. Stepnowski, P. (2008b). Identification and characterization of surface lipid components of the dried-bean beetle Acanthoscelides obtectus (Say) (Coleoptera Bruchidae). Journal of Stored Products Research, Vol.44, No.4, pp. 386-388, ISSN 0022-474X... 

Me ester [28066-21-9]. Sex attractant of the male dried bean beetle (Acanthoscelides obtectus). Light yellow oil. [a] —162° (c, 0.95 in hexane). 

Acanthoscelides obtectus Bean weevil Coleoptera Bruchidae Acrolepiopsis assectella Leek moth... 

R. officinalis L. (Lamiaceae) can be found in the Mediterranean area. The used parts are the fresh owering tops. The essential oil can be used as antipest due to its effect on beetles, caterpillar larvae, and many other insects (Dayan et ah, 2009) like Drosophila auraria (Konstantopoulou et ah, 1992), Sitophilus oryzae (Lee et ah, 2004), or Rhyzopertha dominica (Shaaya et ah, 1991). The microencapsulated essential oil also showed larvicidal effects on Lymantria dispar (Moretti et ah, 2002). In Acanthoscelides obtectus males and females, R. officinalis volatile oil also caused high mortality rates (Papachristos and Stamopoulos, 2002). Repellent activity was reported against Listronotus oregonensis (Niepel, 2000). 

Papachristos, D. P. and D. C. Stamopoulos, 2002. Repellent, toxic and reproduction inhibitory effects of essential oil vapours on Acanthoscelides obtectus (Say) (Coleoptera Bruchldae). ... 

Szentesi, A. (1981) Pheromone-like substances affecting host-related behavior of larvae and adults in the dry bean weevil, Acanthoscelides obtectus. Ent. exp. appl., 30, 219-26. 

Table 138.1 Toxicity of some essential oils on Acanthoscelides obtectus Say (Coleoptera Bruchidae)... 

Regnault-Roger C, Hamraoui A (1994) Reproductive inhibition of Acanthoscelides obtectus Say (Coleoptera), brachid of kidney bean Phaseolus vulgaris L.) by some aromatic essential oils. Crop Prot 13(8) 624—628... 

The allenic ester produced by the male Dried Bean beetle (Acanthoscelides obtectus), with a half-life of only 10 h at room temperature or 20 days at — 13°C, has been identified as (—)-methyl tetradeca-/m/w-2,4,5-trienoate and its ( )-isomer has been synthesized. ... 

The Coleoptera (beetles) contains about 300,000 species and are very varied in form, diet and habitat. Equally they have very different kinds of pheromones and defensive secretions, many of them derived from fatty acids. The bean weevil Acanthoscelides obtectus uses an unusual allenic methyl ester (Figure 3.25). Its biosynthesis has not yet been investigated. Allenes are an unusual example of chirality. Anomala cuprea, a chafer grub produces two lactone sex attractants, derived from the unsaturated acids oleic and palmitoleic acids (Figure 3.25). Both are shortened by the loss of two acetic acid units, then oxidized (stereospecifically) at the allylic position and cyclized to the pheromone. 

By synthesizing both enantiomeric forms of the dried bean beetle (Acanthoscelides obtectus) sex pheromone, Pirkle and Boeder (634) determined that the natural pheromone had the i -( —) conriguration (11 a). 

Kocienski, P. J., G. Cerniglario, and G. Feldstein A synthesis of ( )-methyl n-tetradeca-rra 5-2,4,5-trienoate, an allenic ester produced by the male dried bean beetle Acanthoscelides obtectus (Say). J. Org. Chem. 42, 353—355 (1977). 

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