Notes 1347

Identification of the Sex Pheromone was shown by the fraction of Rf 0.6—0.8 correspond­ of Borer orbonalis ing to a long chain acetate, and no notable activity by Guenee (: Pyralidae) the remaining fractions. Zhu Pingchou*, Kong Fanlei, Yu Shengdi, GC-MS(EI) analysis of the active fraction from Yu Yongqing, Jin Shuping, Hu Xinhua, TLC separation on SE-54 capillary column recorded and Xu Jianwei a major peak at 17'49" which possessed the following Jiangsu Institute of Pheromones and Hormones fragment ions, mle 222 (M~ — CH3COOH), 194 Jintan, Jiangsu, (C14Ht6), 180 (C 13Ht4), 166 (C 12m 2), 152 (C „H t0), Z. Naturforsch. 42c, 1347—1348 (1987); 138 (C10H |8), 124 (C9H |6), 110 (C8H |4), 96 (C7H |2), 82 received May 11, 1987 (C6H |0) and 61 (CH3COOH2). These data indicated Sex Pheromone, Identification, , that the natural pheromone is a «-hexadecenyl ace­ Lepidoptera, 11-Hexadecenyl Acetate tate [2]. (£)11-Hexadecenyl acetate was identified from sex To determine the location of the double bond, pheromone gland extract of female eggplant borer. The microozonolysis [3, 4] was carried out. GC-MS acetate synthesized in the laboratory showed high attrac- (methane Cl) of the ozonolysis product on a tant activity in the field. PEG-20M capillary column showed a major peak at 6'36" with parent ion at mle 229 (M H+), and less The eggplant borer, Leucinodes orbonalis Guenee ion at mle 169 (MH-CH3COOH) and 151 (Lepidoptera: Pyralidae), is a serious pest of egg­ (MH—CH3COOH —H20). These data indicated that plant in various regions of China [1], The control of the ozonolysis product of pheromone was this pest is troubled with the fact that the chemical 11-acetoxyundecanal, and thus showed that the double insecticides do not penetrate into the fruit where the bond of the pheromone is located at 11-position. pests stay. The female sex pheromone identified and The configuration of the double bond was ex­ synthesized as follows might be a prospective candi­ amined by comparing the GC retention time (/?,) of date for population monitoring or direct control. the natural pheromone to that of synthetic ( E )- and The abdominal tips of virgin female were (Z)-l 1-hexadecenyl acetate (Ia and Ib). /?t of the immersed in «-heptane for 6 h. This crude extract synthetic Ia and Ib on a DEGS capillary column were was fractionated by preparative TLC on a silica gel 16'40" and 17'20" respectively, while that of natural plate and developed with n-hexane-ethyl ether (4:1). pheromone was 16'40". Thus, Z configuration was The absorbate was cut into five fractions and washed defined. with treated acetone. In the field test, high bioactivity Synthesis of Ia and Ib was carried out as follows:

■ # ^ 0H

-> Ia

OTHP -> Ib

where a— NaH/l,2-EDA, b— DHP, H ,0 1 c— n-BuLi/BuBr, d— Na/Liq NH3, e— Hi, P—2Ni, f— AcOH-AcCl.

Reprint requests to Zhu Pingchou. Verlag der Zeitschrift für Naturforschung, D-7400 Tübingen 0341-0382/87/1100-1347 $01.30/0 1348 Notes

In the electroantennagram (EAG) "puff" test at were captured by traps baited with 300 to 500 |ig Ia 10 ng level, the males responded much stronger to than by six alive females. This result proved that Ia is synthetic Ia than to Ib. In field trapping, Ia was found the main component of the eggplant borer sex to be very attractive to male moths, and more males pheromone.

[1] a) Plant Diseases and Pests in China. Vol. 2, [2] Ando Tetsu, Kishino Kenichi. Tatsuki Sadahiro. and p. 1493. Agriculture Publ. Beijing 1981; Takahashi Nobutaka, Agric. Biol. Chem., 44, 765 b) Zhu Shuxun, Kunchong Zhishi (Popular Entomolo­ (1980). gy) 1980, 262, 271; [3] M. Beroza and B. A. Bierl, Anal. Chem. 39, 1131 c) Yang Ziqi. Kunchong Zhishi (Popular Entomology) (1967). 1982 (2), 20; [4] B. F. Nesbitt, P. S. Beevor, D. R. Hall. R. Lester, and d) Hu Quanxiao, Zhiwu Baohu (Plant Protection) J. R. Williams, J. Chem. Ecol. 5, 385 (1980). 1983 (4). 22.