• Journal of the Korean Chemical Society
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• v.32 no.1
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• pp.60-64
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• 1988

Synthesis and biological activity test are described for the (Z)-11-hexadecen-1-ol, (Z)-11-hexadecen-1-yl acetate, and (Z)-11-hexadecen-l-al, the sex pheromone of the diamond back moth, Plutella xylostella L.. Lithium acetylide was alkylated with 10-bromodecan-1-ol THP ether to give 11-hexadecyn-l-ol THP ether. 11-Hexadecyn-l-ol THP ether was stereoselectively reduced over Pd/BaSO4to yield (Z)-11-hexadecen-l-ol THP ether, which was in turn deprotected to provide (Z)-11-hexadecen-l-ol. (Z)-11-Hexadecen-l-ol was acetylated and oxidized to afford (Z)-11-hexadecen-1-yl acetate and (Z)-11-hexadecen-l-al, respectively. Biological activity test of the synthetic compounds, (Z)-11-hexadecen-l-ol, (Z)-11-hexadecen-1-yl acetate, and (Z)-11-hexadecen-l-al in the ratio of 0.1 : 5 : 5 was tested in the field using polyethylene capsules as containers. The numbers of moth trapped with pheromone vials were counted.

• Korean Journal of Plant Taxonomy
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• v.50 no.2
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• pp.148-153
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• 2020

Cleisostoma scolopendrifolium is an orchid species solely pollinated by the male bee Megachile yasumatsui. Although C. scolopendrifolium is an endangered species in Korea, little is known about its pollination mechanisms or the profiles of its chemical attractants. This study provides evidence that the Cleisostoma orchid attracts male bees as pollinators by mimicking female mating signals. We found 13 hydrocarbons in the Cleisostoma orchid flower presumed to be involved in sex pheromone mimicry: five alkanes (tricosane, pentacosane, heptacosane, nonacosane, and hentriacontane), compounds of cuticular hydrocarbons which function as chemical cues for the recognition of mates and species in social insects; and eight alkenes ((z)-9-tricosene, (z)-9-pentacosene, (z)-11-pentacosene, (z)-9-heptacosene, (z)-11-heptacosene, (z)-9-nonacosene, (z)-11-nonacosene, and (z)-11-hentriacontene) which serve as sex pheromones in several insects. We suggest that these hydrocarbons play a key role in the pollination mechanism between Cleisostoma orchids and Megachile bees.

• Korean journal of applied entomology
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• v.40 no.3
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• pp.219-226
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• 2001

To identity the composition and ratio of the sex pheromone in the asiatic leafroller, Archippus breviplicanus (Walsingham), which is a major pest on apple leaves, and to develop a monitoring system using this sex pheromone, abdominal tips of their virgin female during the calling period were extracted and analysed. The GC/GC-MS analysis revealed the following three compounds; (E)11-tetradecenyl acetate (E11-14: Ac), (Z)11-tetradecenyl acetate (Z11-14: Ac), and tetradecyl acetate(14: Ac) with the ratio of 56:22:22. Electroantennogram (EAG) assay was also conducted to examine biological activity of the components. The three components evoked significantly higher responses than hexane or air but there was no significant differences between the mixtures made by components. Field trapping experiments for determining the optimum blend, seasonal fluctuation and the optimum amount for male attracting were carried out over 4 years from 1997 to 2000. Although male moths were attracted to 8:2 and 7:3 between E11-14: Ac and Z11-14: Ac, their 7:3 blend was found to be the most effective. Archippus breviplicanus appears to occur three times a year in Korea. The optimum amount for monitoring was found to be 1mg per trap. 14: Ac, the third component, did not show synergistic effect on male moth attraction.

• Korean journal of applied entomology
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• v.42 no.2
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• pp.111-118
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• 2003

The population density of the Cotton caterpillar, Palpita indica (Saunder) larvae was gradually increased until 10th October and then decreased rapidly after that time at the watermelon culture of rain sheltered house. After 15th October, many larvae went to soil and molted to pupae for the hibernation. Most of pupae were found in pF 2.4 soil moisture condition, but none in pF 1.5 hydro-morphic soil. Most of the pupae were found below 5cm and there was no pupa below 10cm from the soil surface. The sex ratio of the overwintering pupae was 1.09 : 1.00. For the monitoring of the cotton caterpillar adults using sex pheromone compounds, different mixture ratios of each pheromone compound were investigated with (E)-11-hexadecenal and (E, E)-10,12-hexadecadienal. Seven versus three ratio of (I)-11-hexadecenal and (E, E) -10,12-hexadecadienal was more attractive than any other ratio, and then followed by 6 : 4, 8 : 2, 9 : 1, and 5 : 5 mixtures. As a result of monitoring with 7 : 3 mixture of (E)-11-hexadecenal and (E, E)-10,12-hexadecadienal, occurrence peaks of cotton caterpillar adults showed 4 times per year. The first time of adult appearance was late July in 2000 and middle July in 2001 and the highest number was collected on late September.

• Applied Biological Chemistry
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• v.34 no.2
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• pp.110-116
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• 1991

As the model compounds, citral and n-octanol which possess similar characteristics and structures of low molecular weight insect pheromones and $({\pm})-5-hydroxy-4-methyl-heptan-3-one$ which shows the aggregation pheromones activity of the rice weevil and the maize weevil were microencapsulated with low molecular weight polyethylene(LMPE) and urea-formaldehyde resin as wall materials. The core materials were microencapsulated as small particles in LMPE and urea-formaldehyde resin polymers and the microencapsulated polymers were white powders. And the polymer made from urea-formaldehyde resin was better than that from LMPE as wall material. The slow releasing effect and the releasing patten of the microencapsulated core materials were examined by solvent extraction method and headspace sampling method. Citral and n-octanol and $({\pm})-5-hydroxy-4-methyl-heptan-3-one$ were release more than 40 days and 15 days, respectively. The releasing pattern of urea-formaldehyde resin microcapsules showed rather smooth decrease than that of LMPE and was maintained at steady level longer.

• Reproductive and Developmental Biology
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• v.28 no.1
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• pp.45-52
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• 2004

To search a new porcine pheromonal odorants, this research for biostimulation and role of pheromone was augmented by means of "control system technologies" to offer a potentially useful and practical way to improve reproductive efficiency in livestock species. Therefore the 13 physicochemical parameters such as similarity indice (S), hydrophobicity (logP) and van der Waals molecule volume (MV) etc. of 54 steroid analogues, which are analogous of substrate molecules, 5$\alpha$-androst-16-en-3-one (P1) and 5$\alpha$-androst-16-en-3-ol (P2) of lipocalin as receptor of pig pheromones were calculated and discussed. The physicochemical properties of these steroid analogues were mainly followed by steric dissimilar of A and D ring in steroid nucleus. And we found that from correlation with S values and MV constants of molecules, the more MV constants are small, the more S values tend to approach 1. Based on this results, the S-values of 4-androsten-3,17-dione (P1-1) and 5 $\alpha$ -androstan-3-one (P2-1) were 1.0, respectively. The two compounds of them were chosen because they showed the same value each other at a side of hydrophobicity, molar refractivity and molecular volume. It is expected that the new two compounds will be able to substitute for P1 and P2, porcine pheromonal odorants.

• Korean journal of applied entomology
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• v.60 no.1
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• pp.91-98
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• 2021

The populations of Riptortus pedestris (Fabricius) cause serious economic damages in local apple orchards. However, there was no study to manage its populations with environment friendly tactics. Thus, this study was conducted to analyze its attraction effects of one of R. pedestris aggregation pheromone compounds, (E)-2-hexenyl (Z)-3hexenoate (E2HZ3H), to its parasitoids, Ooencyrtus nezarae (Ishii) and Gryon japonicum (Ashmead). This compound did not increase the number of these two parasitoids and change its spatial distribution. However, this compound could attract two parasitoids within limited distance. These results indicates that one compound of R. pedestris aggregation pheromone, E2HZ3H, could be a good candidate to manage R. pedestris populations in conditions that its populations locally occurs in apple orchards.

• Korean journal of applied entomology
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• v.61 no.1
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• pp.77-83
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• 2022

This study was conducted to determine the optimal composition of sex attractant for monitoring adults of the tobacco cutworm, Spodoptera litura, in Korea. Lures of different compositions from the two sex pheromone components the female, (Z,E)-9,11-tetradecadienyl acetate (Z9E11-14:Ac) and (Z,E)-9,12-tetradecadienyl acetate (Z9E12-14:Ac), were compared for male attraction using synthetic chemicals, rubber septa, and funnel traps in soybean and peanut fields. After sequential tests were conducted using three sets of the two components different ranges from 5:5 to 10:1, from 9:1 to 99:1, and from 9:1 to 39:1, the 19:1 ratio was identified as the most efficient composition. However, S. litura males were barely caught in the trap of the Z9E11-14Ac single component lure. The results show that both the sex attractant compounds are necessary for monitoring adults S. litura males. The higher the pheromone amount in the dispenser in the range from 0.1 to 10 mg, the more males were attracted. Furthermore, the trap height of 1.5 m was optimal for male capture.

• Korean journal of applied entomology
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• v.61 no.1
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• pp.51-62
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• 2022

Numerous insect pests threaten the Korean orchard industry through feeding on various tissues of fruit trees. Generally, the control of economically important orchard pests is based on the use of chemical insecticides. Owing to growing concerns regarding the environmental and human health effects of insecticides, environment-friendly pest control strategies are urgently needed. Pheromones of orchard pests could lead to an environmentally safe control system based on mating disruption or mass trapping. This review summarizes the functions and compounds of known pheromones from 51 orchard pests in Korea. The pheromones identified to date from 14 species in the families Miridae, Aphididae, Diaspididae, Pseudococcidae, Rutelidae, Cecidomyiidae, and Eurytomidae and 26 species in the order Lepidoptera are female-produced sex pheromones that attract only males. In contrast, all known examples for 11 species in the families Alydidae, Pentatomidae, Thripidae and Cerambycidae are male-produced aggregation pheromones that attract both sexes. Research on pheromones in new pests, kairomones in key orchard pests, mating disruption dispensers to generate prolonged release of the pheromones, and trap design and trap location for mass trapping will be required for the expanded use of pheromones and other semiochemicals in orchard pest management in the future.

• Korean journal of applied entomology
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• v.57 no.3
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• pp.209-220
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• 2018

Mating disruption (MD) has been widely used to effectively control Grapholita molesta in apple orchards. A simultaneous mating disruption (SMD) techniques have been developed to control both G. molesta and G. dimorpha. This study was performed to determine the practical parameters to apply the SMD technique to field conditions. To determine the application amount of SMD lures, a dispenser containing 10 mg pheromone was placed at different numbers of trees in an orchard. Application at every other tree (= one dispenser per two trees) was relatively safe to expect effective MD efficiency in both wax and polyethylene (PE) formulations. One time application at the end of March was enough to maintain a year round MD efficacy against both species. A fence treatment using food trap was applied to prevent any immigratory mated females from nearby untreated regions. To enhance the food trap by adding host-derived secondary compounds, terpinyl acetate (TA) was screened to be effective to attract females of Grapholita molesta among six compounds contained in apple fruit extracts. Among different TA concentrations, 0.05% TA treatment was the most effective to attract the adults. A mixture of TA and sugar was effective to attract and kill females and called FAKT (female attract-to-kill techniques). FAKT was treated at approximately 6 m interval at the edge of the apple orchards. The females trapped by the FAKT included mated females possessing vitellogenic oocytes. SMD supplemented with FAKT maintained the high MD efficacy and significantly suppressed leaf damage induced by the two insect pests compared to control or single SMD treatment.