Sexually differentiated functions of female-produced pheromone of the black chafer <Emphasis Type="Italic">Holotrichia loochooana loochooana</Emphasis> (Sawada) (Coleoptera: Scarabaeidae)

Summary. Both male and female Holotrichia loochooana loochooana (Sawada) (Coleoptera: Scarabaeidae) were attracted with female-produced pheromone, anthranilic acid (2-aminobenzoic acid), in the field. Male chafers were observed to apparently directly locate cotton balls impregnated with 1 to 10 mg of pheromone. In contrast, females never directly oriented to the treated balls but landed 0.2-1.5 m away and exposed their abdominal glands in a calling posture, which occasionally resulted in aggregation of both females and males. This suggested the mating aggregation of this species could be primarily induced by pheromone released by females. A hypothesis for adaptability of female aggregation is proposed and discussed.     

Polychlorinated dibenzothiophenes in Japanese environmental samples and their photodegradability and dioxin-like endocrine-disruption potential

Polychlorinated dibenzothiophenes (PCDTs) in sediment, soil, and fly ash samples collected in Japan were analyzed and their dioxin-like endocrine-disruption potential and photodegradability investigated. PCDTs were detected in all three types of sample, although the concentrations were lower than those of polychlorinated dibenzo-p-dioxins (PCDDs) and polychlorinated dibenzofurans (PCDFs). An Ah-immunoassay confirmed that 2,3,7,8-TeCDT, 1,2,3,7,8-PeCDT, 1,2,3,7,8,9-HxCDT, and 1,2,3,4,7,8,9-HpCDT had Ah receptor-binding activities, which means that these PCDTs have the potential to cause dioxin-like endocrine-disruption. Photodegradation of PCDTs by UV irradiation was accompanied by dechlorination. The photodegradation rates of 2,3,7,8-TeCDT and OCDT were lower than the rates for the corresponding PCDF isomers (2,3,7,8-TeCDF and OCDF), which indicates that PCDTs are more stable than PCDFs to photodegradation.     

Photodechlorination of octachlorodibenzothiophene and octachlorodibenzofuran: comparison of experimental degradation pathways with degradation pathways predicted by DFT

Polychlorodibenzothiophenes (PCDTs) are sulfur analogues of polychlorodibenzofurans (PCDFs) and have been detected in environmental samples. We used density functional theory calculations (Gaussian 98W) to predict the photodechlorination pathways of octachlorodibenzothiophene (OCDT) and octachlorodibenzofuran (OCDF) in hexane, and we compared the predicted pathways with those observed during UV irradiation experiments. OCDT and OCDF were observed to degrade through first-order dechlorination processes, and the rate constant for OCDT was less than one-third that for OCDF. The main experimental photodechlorination pathways of OCDT and OCDF led to hexachlorinated and tetrachlorinated congeners, respectively; that is, the photodechlorination pathway of OCDT differed from that of OCDF. On the assumption that the dechlorination mechanisms involved radical reactions, we used DFT calculations to estimate bond-dissociation energies and single-point energies of OCDT and OCDF and their dechlorinated congeners, and we used the resulting information, along with hypotheses regarding the rate-controlling step of the degradations, to predict theoretical degradation pathways. We propose that reaction of dechlorinated radicals with a hydrogen donor was the rate-controlling step for OCDT and that C-Cl bond dissociation by UV light was the rate-controlling step for OCDF.     

Anthranilic acid: a free amino‐acid pheromone in the black chafer, <Emphasis Type="Italic">Holotrichia loochooana loochooana</Emphasis>

Summary. Ether extract of the abdominal gland of female black chafers Holotrichia loochooana loochooana (Sawada) (Coleoptera: Scarabaeidae) induced a series of pre-mating behaviors that included short-distance orientation, mounting and abdominal bending toward females in the laboratory. When the extract was chromatographed on a silica gel column, the activity was eluted with 50% ether in hexane and ether fractions. GC-MS analyses revealed that both the active fractions contained anthranilic acid (2-aminobenzoic acid) as a major compound. When partitioned to basic, acidic and amphoteric fractions, pheromonal activity was observed with the latter two fractions and anthranilic acid was detected in these fractions by HPLC analyses. The amount of anthranilic acid in the female extract was estimated to be ca. 1.3 μg/female. Authentic anthranilic acid induced pre-mating behavior in males of at levels equal to that elicited by the compound in the extract. It also attracted male beetles to the traps in the field. Received 29 October 2002; accepted 9 January 2003. R1D=" Correspondence to:Hiroe Yasui, e-mail:yasui@affrc.go.jp