Cryptolestes beetles

Direct behavioral evidence of how stored-product insects move among patches is limited, but what is available shows that stored-product pests readily leave patches of food, can find and exploit multiple patches, and that these processes are influenced by a variety of endogenous and exogenous factors. The time Cryptolestes ferrugineus spent in refugia has been shown to be influenced by strain, sex, and age (Cox and Parish, 1991 Cox et al., 1989, 1990). A variety of factors have been shown to influence the decision by red flour beetles to leave food patches, including insect density... 

Advent of ring-closing olefin metathesis reaction has influenced the synthetic strategy of pheromones very much. For example, the racemate of a macrolide pheromone such as (5Z,13S)-5-tetradecen-13-olide (29) (aggregation pheromone of the flat grain beetle, Cryptolestes pusillus) could readily be synthesized as shown in Scheme 42 [67]. Unfortunately, ( )-29 prepared by this method was a mixture of c/s, trans-isomers (Z/E=69 31). (S)-5-Hexadecanolide (27) was also synthesized by means of ring-closing olefin metathesis as shown in Scheme 43 [68]. 

Vanderwel D., Pierce H. D. Jr, Oehlschlager A. C., Borden J. H. and Pierce A. M. (1990) Macrolide (Cucujolide) biosynthesis in the rusty grain beetle, Cryptolestes ferrugineus I. Insect Biochem. 20, 567-572. 

A39 Anomala, scarab beetles 326 A40 Cryptolestes, cucujiid beetles 347... 

A41, A42 Cryptolestes, cucujiid beetles 347 A43, A44 Orycaephilus, cucujiid beetles 348... 

Smith, L.B. (1970) Effects of cold acclimation on supercooling and survival of the rusty grain beetle, Cryptolestes ferrugineus (Stephens) (Coleoptera Cucujidae) at sub-zero temperatures. Canadian Journal of Zoology 48, 853-858. 

Smith, L.B. 1977. Efficiency of Berlese-Tullgren funnels for removal of the msty grain beetle, Cryptolestes ferrugineus, from wheat samples. Can. Entomol. 109, 503-509. 

Some macrolides are used as aggregation pheromones. Ferralactones I (= cucu-jolide 1,155) and II (156) are 11- and 12-membered ring macrolides, respectively, produced by the rusty grain beetle Cryptolestes ferrugineus [182]. (Z)-3-Dodecen-12-olide (157) and cucujolide HI (158) are 13- and 14-membered ring macrolides, respectively, produced by C. pusillus and C. turcicus, respectively [183,184]. 

A. V. (1985). Aggregation pheromones of the flat grain beetle, Cryptolestes pusillus (Coleoptera Cucujidae). J. Chem. Ecol. 11, 1053-1070. 

Cucujoides. Group of unsaturated macrocyclic lactones with 12 or 14 carbon atoms identified as pheromones of the saw-toothed grain beetles of the genera Cryptolestes and Oryzaephilus. Some of these compounds, which occur in differing mixtures in the different species, are chiral and species-specific. Enantiomer ratios have also been observed, see also ferra-lactone II. 

C12H20O2. Mr 196.29. A pheromone belonging to the group of cucujolides of male grain beetles. While Cryptolestes ferrugineus produces the (5)-enantiomer, Oryzaephilus mercator uses the (Zi)-enantiomer as an attractant. ... 

Evaluation of spinosyns as a protectant for stored grains has also been reviewed [11]. Excellent control of Lesser grain borer Rhyzopertha dominica (E.) [12-14], Indianmeal moth Plodia interpunctata), and other grain beetle pests (e.g., Tribo-lium, Cryptolestes, Sitophilus, Oryzaephilus, Prostephanus) has been demonstrated... 

Figure 3.38 Macrocyclic lactones from beetle aggregation pheromones. Compound A is found in Cryptolestes pusillus, the flat grain beetle, compounds Band E in C. surinamensis, a mixture of enantiomers of C in C. turcicus, compound D and the R-enantiomer of E in C. ferrugineus, the rusty grain beetle...

The aggregation pheromone of the rusty grain beetle Cryptolestes ferrugineus is a mixture of large ring lactones called cucujolides... 

Rat grain beetle Cryptolestes pusUlus Rusty grain beetle Crystolestes ferrugineus... 

---