Dried bean beetle

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... 

Furan has served as a starting material for the synthesis of methyl rt-tetradeca-frans-2,4,5-trienoate (177), a compound presumed to be a sex attractant of the male dried bean beetle (72TL3777). Conversion of furan to 4,4-dimethoxy-frans-but-2-en-l-al (174) was accomplished in two steps by a previously reported procedure. Intermediate (174) was then ethynylated, acetylated and reacted with lithium dioctylcuprate to yield allene (176). Hydrolysis of the acetal and Mn02-NaCN oxidation of the aldehyde afforded the methyl ester (177 Scheme 37). 

Dried bean beetle Adzuki bean weevil Cowpea beetle Mexican bean weevil... 

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). 

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. ... 

Asymmetric acetylation of ( )-40 with vinyl acetate and lipase PS furnished (R)-acetate 41 and (S)-alcohol 40. The former was converted to the axially chiral pheromone of the dried bean beetle (Figure 24.21) [25]. 

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). 

Landor, P. D., S. R. Landor, and S. Mukasa Synthesis of ( )-methyl tetradeca-rraw5-2,4,5-trienoate, the allenic sex pheromone produced by the male dried bean beetle. Chem. Commun. 1971,1638—1639. 

Descoins, C., C. a. Henrick, and J. B. Siddall Synthesis of a presumed sex attractant of dried bean beetle. Tetrahedron Lett. 1972, 3777—3780. 

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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