Appl. Entomol. Zool. 39 (3): 521–526 (2004) http://odokon.ac.affrc.go.jp/
Repellency of hinokitiol against the cigarette beetle, Lasioderma serricorne (Fabricius) (Coleoptera: Anobiidae)
Masatoshi HORI† Leaf Tobacco Research Center, Japan Tobacco Inc.; Oyama, Tochigi 323–0808, Japan (Received 2 December 2003; Accepted 30 April 2004)
Abstract Behavioral responses of the cigarette beetle to 73 chemicals were investigated with an olfactometer. The beetles were strongly repelled by hinokitiol (b-thujaplicine). The frequency of entering choice tubes treated with hinokitiol was significantly less than that of the control tubes. The resident time in the sample tubes was shorter than that in the con- trol tubes. The repellency of hinokitiol in the presence of cured tobacco odor, which attracts beetles, was evaluated. Hinokitiol strongly repelled the beetles at a dose of 1 mg even in the presence of the tobacco odor. However, the con- tact and fumigant toxicity of hinokitiol against the beetles was not strong. The repellency of other troponoid com- pounds, tropone and tropolone, and other compounds with isopropyl groups were weaker than hinokitiol. Therefore, it appears both the tropone ring and isopropyl group play an important role in the strong repellency of hinokitiol.
Key words: Cigarette beetle; hinokitiol; Thujopsis dolabrata; repellent; olfactometer
and Khan, 1994), crude leaf extracts of Tecoma INTRODUCTION stans, Datura matel, Vinca rosea, Coleus barbatus The cigarette beetle, Lasioderma serricorne and Vitex negundo (Ambadkar and Khan, 1989) (Fabricius), does not damage only cigarettes and and various plant essential oils such as shiso oil, cured tobacco leaves but also a wide range of prod- savory oil, cassia oil, thyme oil, peppermint oil, ucts, including cereals, cereal products, cocoa Litsea cubeba oil (Hori, 2003). The main active beans, oilseeds, pulses, spices, dried fruits and component of shiso oil is ( )-perillaldehyde (Hori, some animal products (Hill, 1990). This pest is 2004). mainly controlled by sanitization, remodeling In this study, the repellency of plant components equipment and fumigation at present. However, and chemicals that showed repellency and toxicity there are few control methods that can directly pre- against some arthropod pests was investigated. Hi- vent the beetles from invading the above products. nokitiol had a stronger repellency against the ciga- Repellents would be a useful tool in an integrated rette beetle than chemicals and essential oils management program to control this pest, because known as repellents. The strong repellency of hi- they could inhibit the beetles from invading the nokitiol to the cigarette beetle is reported in this products. paper. The cigarette beetle is attracted to favored food sources such as cured tobacco leaves, toasted cof- MATERIALS AND METHODS fee meal (Kohno et al., 1983), turmeric and fennel (Yadav and Tanwar, 1985; Jha and Yadav, 1991, Insects. The cigarette beetles used for tests were 1998). In contrast, this pest is repelled by some obtained from cultures that have been maintained plant leaves such as Rauwolfia canescens, Vinca for several years in the laboratory. They were rosea, Tamarindus indica, Euphorbia neriifolia, reared on cured tobacco powder in plastic contain- Acalypha hispida and Coleus barbatus (Ambadkar ers (130 mm in diameter, 73 mm high) at 27 2°C
†Present address: Laboratory of Insect Science and Bioregulation, Graduate School of Agricultural Science, Tohoku University, Sendai 981–8555, Japan. E-mail: [email protected] DOI: 10.1303/aez.2004.521
521 522 M. HORI and 70 5% relative humidity. Females of the bee- placed in the sample jar. As a control, a piece of tle attracted by odor of stored products oviposit in filter paper treated with acetone was placed in the these products. Larvae hatch and feed on the prod- control jar. In the test for evaluating the attractive- ucts causing damage to them. If females can be ness of cured tobacco, cured tobacco powder (2 g) prevented from entering the products, the risks of was placed in the sample jar and nothing placed in product losses caused by the beetles can be re- the control jar. In the assay for the presence of to- duced. Therefore, only adult females were used for bacco odor, a piece of filter paper treated with sam- all experiments. Four to 8-day-old adult females ple was placed on the tobacco powder in the sam- were collected from the rearing containers and ple jar and a piece of control filter paper without used for all experiments. tobacco powder was put in the control jar. All tests Chemicals. Anisol, benzyl benzoate, n-butyl were carried out under light conditions at 24–26°C. carbitol acetate, ( )-camphor, cuminaldehyde, di- Each experiment was replicated four times. The allyl disulfide, dimethyl phthalate, hinokitiol, ind- data of the four replications were pooled and trans- alone, isopulegol, myrcene, nerol, neryl acetate, formed to the excess proportion index (EPI) ac- pulegone, safrol and isoamyl salicylate were ob- cording to the following formula: tained from Tokyo Kasei Kogyo Co., Ltd. (Tokyo, EPI (ns nc)/(ns nc) 2PS 1 Japan). Anethole, azulene, benzyl salicylate, bor- PS ns/(ns nc) neol, bornyl acetate, l-( )-carvone, 1,8-cineole, cinnamyl acetate, citronellal, ( )-citronellol, cou- where ns and nc represent the total number of bee- marin, tropone, p-cymene, dibutyl phthalate, dibu- tles in the sample tubes and in the control tubes, re- tyl sebacate, dibutyl succinate, diethyl phthalate, spectively, and PS represents the proportion of bee- eugenol, 2-ethyl-1,3-hexanediol, ( )-fenchone, tles in the sample tubes (Sakuma and Fukami, ( )-fenchone, 2-furaldehyde, geraniol, geranyl ac- 1985). The 95% fiducial limits of PS were calcu- etate, isoeugenol, isosafrole, (Z)-jasmone, ( )- lated from the critical values of the variance ratio F limonene, linalyl acetate, methyl eugenol, ( )-neo- and then transformed into those of EPI. When the menthol, n-octyl alcohol, phenylacetaldehyde, 3- upper limit of the 95% fiducial limit was below 0, phenylpropyl acetate, phenyl salicylate, piperonal, it was concluded that beetles were repelled. When salicylaldehyde, a-terpinene and tropolone were the lower limit of the 95% fiducial limit was above obtained from Wako Pure Chemical Ind. Ltd. 0, it was concluded that beetles were attracted. (Osaka, Japan). ( )-Camphene, carvacrol methyl When the upper limit of the 95% fiducial limit was ether, ( )-carveol, (S)-( )-carvone, N,N-diethyl- 0 or above and the lower limit was 0 or below, it m-toluamide, ( )-fenchol, linalool oxide, ( )- was concluded beetles were neutral to the treat- menthofuran, ( )-menthone, ( )-(1R)-menthyl ac- ment. etate, 3-octanol, 1-octen-3-ol, ( )-perillaldehyde, Observation of behavioral responses to hi- ( )-perillyl alcohol, R-( )-a-phellandrene, ( )- nokitiol. Behavioral responses of the beetles to hi- trans-pinocarveol, terpinene-4-ol and ( )-a-ter- nokitiol in the olfactometer were observed for 1 h. pinyl acetate were obtained from Sigma-Aldrich A piece of filter paper treated with 1 mg hinokitiol Co. (St. Louis, Missouri). was put in the sample jar and a piece of control fil- Assay for evaluating repellency of chemicals. ter paper in the control jar. One adult female was An 8-armed olfactometer was used for the assays. released into the olfactometer. Assays were carried The olfactometer and methods were essentially the out under light conditions at 24–26°C. The behav- same as those described in a previous paper (Hori, ior of the beetle was recorded with a video system. 2003). Fifty adult female beetles were released in The video system consisted of a CCD camera the olfactometer furnished with 8 tubes and con- (Panasonic WV-BL90), a time-lapse video cassette nected to the sample or control jar on the side wall. recorder (Panasonic AG-6730) with a time record- The total number of beetles in the four sample ing function and a video monitor (Sony PVM- tubes was compared with the four control tubes 3 h 146J). After recording, the behavior of the beetles after the beginning of the test. A piece of filter recorded with the cassette tape was reproduced and paper (ADVANTEC, No. 2, 10 20 mm) treated the position of the beetles in the olfactometer regis- with a 10 ml acetone solution of each chemical was tered with the elapsed time. Twenty replications Repellency of Hinokitiol 523 were performed. Hinokitiol significantly reduced the frequency of Toxicity test. Toxicity tests were conducted in a entering the tube and resident time. Hinokitiol in- glass dish (60 mm in diameter, 15 mm high). A hibited the beetles from approaching and settling. piece of filter paper (ADVANTEC, No. 2, 60mm The frequency of entering the sample tubes was ca. in diameter) treated with a 565 ml (ca. 20 ml/cm2) 60% that of the control tubes. The total, average acetone solution of hinokitiol was placed on the in- and maximum resident times in the sample tubes side of the bottom of the upside-down lid of the were ca. 30, 50 and 30% of the control tubes, re- glass dish. Twenty adult female beetles were re- spectively. leased on the filter paper and the base of the glass dish was set on the lid. The inner part of the base Repellency of cured tobacco odor treated with was coated with a polishing agent (CRC®, KURE hinokitiol POLYMATE, KURE Engineering Ltd., Tokyo, Cured tobacco without treatment attracted the Japan) to keep the beetles on the filter paper. The beetles (Table 3). Cured tobacco with 0.0001 mg of experiment was conducted at 27 2°C and 70 5% hinokitiol did not attract the beetles. Hinokitiol sig- relative humidity under a photoperiod of 16L : 8D. nificantly repelled the beetles at a dose of 0.1 mg Five replications were performed for each dose. even in the presence of cured tobacco and strongly Toxicity of hinokitiol was evaluated with corrected repelled at a dose of 1 mg. percent mortality. Corrected percent mortalities were calculated by Abbot’s formula (1925) as fol- Toxicity of hinokitiol lows: Contact and fumigant toxicity of hinokitiol were not strong. Hinokitiol did not exhibit toxicity Corrected percent mortality against the beetles at 3 d after application at a dose 100 (P P )/(100 P ) t c c of 0.1 mg/cm2. About 85% of the beetles survived where Pt and Pc represent percent mortality in the 3d after application even when they were exposed treatment and control, respectively. to 0.3 or 1 mg/cm2 hinokitiol.
RESULTS DISCUSSION Behavioral responses to chemicals Hinokitiol (b-thujaplicine) exhibited strong re- The behavioral responses of the beetles to 73 pellency against the beetles even at a dose of chemicals are summarized in Table 1. Thirty-five 0.1 mg. The other chemicals tested did not strongly of the chemicals repelled the beetles and 14 chemi- repel or attracted beetles at a dose of 0.1 mg or cals attracted them at a dose of 1 mg or 1 ml. 0.1 ml. Hinokitiol is found in essential oils ex- Eleven chemicals, which exhibited high repellency tracted from plants such as Thujopsis dolabrata (EPI 0.60) at a dose of 1 mg or 1 ml, were fur- var. hondai, Thuja plicata and Chamaecyparis tai- ther evaluated at a dose of 0.1 mg or 0.1 ml. Hi- wanensis (Okuda, 1968). Recently, hinokitiol has nokitiol and ( )-perillaldehyde repelled the bee- been used in various commodities such as clothes, tles, while ( )-fenchol, safrol, l-( )-carvone, pule- packages for foods, hair restorer, and tooth powder, gone and 3-octanol attracted them at a dose of because hinokitiol has various physiological activi- 0.1 mg or 0.1 ml. The repellency of hinokitiol was ties such as antifungal, acaricidal (Inamori et al., the highest in the chemicals tested and almost all 2000), antimicrobial, metalloprotease inhibitory beetles chose the control tubes at doses of 1 and (Inamori et al., 1999), antitermitic (Nakashima and 0.1 mg. Shimizu, 1972) and phytogrowth inhibitory (Saka- gami et al., 2000). However, there are few reports Behavioral response to hinokitiol in the olfac- on the repellency of hinokitiol to insects. tometer T. dolabrata exhibits antitermitic activity and re- The frequency of entering the tube, the total and pellency to Coptotermes formosanus, and the ac- the average resident times and the maximum resi- tive components are hinokitiol and carvacrol dent time for 1 h were obtained from the measure- (Nakashima et al., 1971; Shimizu et al., 1971; ment of 20 beetles (Table 2). Nakashima and Shimizu, 1972). Lee et al. (1997) 524 M. HORI
Table1. Behavioral response of Lasioderma serricorne to chemicals
Chemicals Doses EPI a (fiducial limits) Chemicals Doses EPI (fiducial limits)
Hinokitiol 1 mg 0.99 ( 1.00, 0.94) Rb ( )-Fenchol 1 mg 0.81 ( 0.89, 0.71) R 0.1 mg 0.96 ( 0.99, 0.90) R 0.1 mg 0.46 ( 0.31, 0.59) A 0.08 mg 0.44 ( 0.57, 0.30) R 1-Octen-3-ol 1 ml 0.82 ( 0.90, 0.71) R 0.05 mg 0.37 ( 0.50, 0.22) R 0.1 ml 0.06 ( 0.21, 0.09) N 0.03 mg 0.17 ( 0.31, 0.02) R 0.01 ml 0.30 ( 0.16, 0.44) A 0.01 mg 0.19 ( 0.34, 0.03) R Terpinene-4-ol 1 ml 0.79 ( 0.87, 0.68) R 0.001 mg 0.07 ( 0.07, 0.22) N 0.1 ml 0.13 ( 0.03, 0.29) N Safrol 1 ml 0.75 ( 0.84, 0.63) R 0.01 ml 0.17 ( 0.02, 0.32) A 0.1 ml 0.35 ( 0.20, 0.48) A Linalool oxide 1 ml 0.71 ( 0.80, 0.59) R ( )-Perillaldehyde 1 ml 0.73 ( 0.83, 0.61) R 0.1 ml 0.07 ( 0.08, 0.22) N 0.1 ml 0.22 ( 0.37, 0.07) R 0.01 ml 0.07 ( 0.08, 0.23) N 0.01 ml 0.10 ( 0.25, 0.05) N l-( )-Carvone 1 ml 0.68 ( 0.77, 0.56) R Pulegone 1 ml 0.66 ( 0.76, 0.53) R 0.1 ml 0.65 ( 0.53, 0.76) A 0.1 ml 0.54 ( 0.40, 0.66) A 3-Octanol 1 ml 0.62 ( 0.74, 0.49) R Diallyl disulfide 1 ml 0.61 ( 0.72, 0.48) R 0.1 ml 0.17 ( 0.02, 0.32) A 0.1 ml 0.00 ( 0.15, 0.15) N Anethole 1 ml 0.59 ( 0.70, 0.46) R 0.01 ml 0.08 ( 0.07, 0.23) N (Z)-Jasmone 1 ml 0.58 ( 0.70, 0.44) R Isopulegol 1 ml 0.58 ( 0.69, 0.45) R n-Octyl alcohol 1 ml 0.57 ( 0.69, 0.44) R Tropolone 1 mg 0.57 ( 0.68, 0.45) R ( )-Neomenthol 1 ml 0.56 ( 0.67, 0.43) R Salicylaldehyde 1 ml 0.55 ( 0.67, 0.40) R Tropone 1 ml 0.54 ( 0.66, 0.41) R Cuminaldehyde 1 ml 0.53 ( 0.65, 0.40) R Eugenol 1 ml 0.49 ( 0.61, 0.35) R (S)-( )-Carvone 1 ml 0.49 ( 0.61, 0.35) R Geraniol 1 ml 0.47 ( 0.60, 0.33) R ( )-Citronellol 1 ml 0.39 ( 0.53, 0.23) R Phenyl salicylate 1 mg 0.36 ( 0.50, 0.21) R Cinnamyl acetate 1 ml 0.35 ( 0.49, 0.19) R Geranyl acetate 1 ml 0.35 ( 0.49, 0.21) R ( )-Camphor 1 mg 0.34 ( 0.49, 0.18) R ( )-Menthone 1 ml 0.33 ( 0.46, 0.18) R Isosafrole 1 ml 0.32 ( 0.46, 0.18) R Neryl acetate 1 ml 0.29 ( 0.42, 0.14) R ( )-Menthofuran 1 ml 0.22 ( 0.36, 0.08) R Isoamyl salicylate 1 ml 0.21 ( 0.35, 0.07) R Benzyl benzoate 1 ml 0.19 ( 0.34, 0.04) R ( )-trans-Pinocarveol 1 ml 0.15 ( 0.29, 0.00) R Isoeugenol 1 ml 0.13 ( 0.28, 0.02) N Piperonal 1 ml 0.13 ( 0.27, 0.02) N Nerol 1 ml 0.13 ( 0.27, 0.02) N Dibutyl succinate 1 ml 0.11 ( 0.26, 0.04) N Citronellal 1 ml 0.10 ( 0.25, 0.05) N n-Butyl carbitol acetate 1 ml 0.10 ( 0.24, 0.05) N 3-Phenylpropyl acetate 1 ml 0.07 ( 0.22, 0.09) N Coumarin 1 ml 0.06 ( 0.20, 0.08) N Methyl eugenol 1 ml 0.05 ( 0.21, 0.10) N ( )-Perillyl alcohol 1 ml 0.04 ( 0.20, 0.13) N Benzyl salicylate 1 ml 0.02 ( 0.17, 0.13) N Dibutyl sebacate 1 ml 0.02 ( 0.17, 0.13) N Borneol 1 mg 0.01 ( 0.16, 0.14) N Anisol 1 ml 0.00 ( 0.15, 0.15) N ( )-Carveol 1 ml 0.01 ( 0.14, 0.16) N ( )-a-Terpinyl acetate 1 ml 0.02 ( 0.13, 0.16) N 2-Furaldehyde 1 ml 0.02 ( 0.13, 0.17) N Azulene 1 mg 0.03 ( 0.12, 0.19) N ( )-Fenchone 1 ml 0.05 ( 0.10, 0.21) N ( )-(1R)-Menthyl acetate 1 ml 0.06 ( 0.09, 0.20) N ( )-Limonene 1 ml 0.07 ( 0.09, 0.22) N N,N-Diethyl-m-toluamide 1 ml 0.08 ( 0.07, 0.23) N Indalone 1 ml 0.08 ( 0.07, 0.23) N Bornyl acetate 1 ml 0.09 ( 0.06, 0.23) N Diethyl phthalate 1 ml 0.16 ( 0.00, 0.31) A R-( )-a-Phellandrene 1 ml 0.17 ( 0.02, 0.32) A Linalyl acetate 1 ml 0.18 ( 0.03, 0.32) A Dibutyl phthalate 1 ml 0.19 ( 0.03, 0.34) A p-Cymene 1 ml 0.19 ( 0.04, 0.33) A Myrcene 1 ml 0.21 ( 0.06, 0.35) A ( )-Camphene 1 ml 0.24 ( 0.09, 0.38) A ( )-Fenchone 1 ml 0.26 ( 0.11, 0.40) A Carvacrol methyl ether 1 ml 0.29 ( 0.15, 0.43) A 2-Ethyl-1,3-hexanediol 1 ml 0.30 ( 0.15, 0.44) A Phenylacetaldehyde 1 ml 0.33 ( 0.18, 0.46) A a-Terpinene 1 ml 0.42 ( 0.27, 0.55) A 1,8-Cineole 1 ml 0.45 ( 0.29, 0.59) A Dimethyl phthalate 1 ml 0.52 ( 0.38, 0.64) A
a Excess proportion index with 95% fiducial limits in parentheses. EPI (ns nc)/(ns nc); ns, nc: total number of L. serricorne in the sample and control tubes, respectively. b R: Repellency (Upper limit of 95% fiducial limits of EPI 0), N: Neutral (Upper limit of 95% fiducial limits of EPI 0, and lower limit of 95% fiducial limits of EPI 0), A: Attraction (Lower limit of 95% fiducial limits of EPI 0). Repellency of Hinokitiol 525
Table2. Behavioral responses of Lasioderma serricorne to hinokitiol in an olfactometer
Frequency of Total resident Average resident Maximum resident Choice tube entering tube time (s) time (s) time (s)
Control 7.45 1.65 1,787.00 266.69 486.10 151.43 1,532.65 263.32 Treatment 4.50 0.92* 533.85 241.77* 246.70 172.06* 500.85 238.50*
Values are means standard errors of 20 beetles. * Significant difference at p 0.05 by Wilcoxon test.
Table3. Repellency of cured tobacco odor with hinokitiol against Lasioderma serricorne
Doses of hinokitiol (mg) EPI a (fiducial limits)
0 (tobacco odor only) 0.62 ( 0.49, 0.73) Ab 0.0001 0.03 ( 0.12, 0.18) N 0.001 0.04 ( 0.19, 0.11) N 0.01 0.12 ( 0.27, 0.03) N 0.1 0.23 ( 0.37, 0.08) R 1 0.86 ( 0.93, 0.76) R
a,b See footnotes in Table 1. reported that crude oil of T. dolabrata sawdust ex- hibited larvicidal activity against Thecodiplosis japonensis and carvacrol was more toxic than hi- nokitiol. Ahn et al. (1998) showed insecticidal and acaricidal activity of components of T. dolabrata sawdust against the arthropod pests, Reticulitermes speratus, Callosobruchus chinensis, Sitophilus oryzae, Plutella xylostella, Myzus persicae, Blat- tella germanica, Tetranychus urticae and L. serri- corne. They showed the active component of T. dolabrata sawdust was carvacrol. Insecticidal activity of hinokitiol against the cig- Fig. 1. Chemical structures of troponoid and other com- pounds having an isopropyl group. arette beetle was weak as supported by the above mentioned results. However, hinokitiol showed a strong repellency against the beetles. Although car- than hinokitiol. Tropolone is a tropone ring substi- vacrol also showed repellency (EPI was 0.62 and tuted with a hydroxy group at the 2 position. Hi- 0.29 at the doses of 1 ml and 0.1 ml, respectively) nokitiol is a tropone ring with a hydroxy and an against the beetles (Hori, 2003), the repellency of isopropyl group substituted at the 2 and 4 posi- hinokitiol was much stronger than that of car- tions, respectively. Therefore, the isopropyl group vacrol. Therefore, in order to elucidate the protec- of hinokitiol may be important in exhibiting the tion mechanisms of T. dolabrata against arthropod strong repellency of this compound. Repellency of pests, we need to investigate not only the toxicity other compounds having an isopropyl group, ter- but also the repellency of hinokitiol. pinene-4-ol, ( )-neomenthol, cuminaldehyde, ( )- Hinokitiol, tropolone and tropone are troponoid menthone, isoamyl salicylate, ( )-(1R)-menthyl compounds with a typical seven-member ring con- acetate, R-( )-a-phellandrene, p-cymene, car- taining three double bonds (Fig. 1). The repellency vacrol methyl ether and a-terpinene, was weaker of tropolone and tropone were the same but weaker than that of hinokitiol or was not exhibited. 526 M. HORI
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