Attractant substance for paracoccus marginatus

Abstract

To provide a composition capable of attracting Paracoccus marginatus.SOLUTION: The use of a compound represented by Formula (1) (where n is 1 to 2) enables attraction of male Paracoccus marginatus and also allows disruption of communication between male and female Paracoccus marginatus.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to attractants for papaya mealybugs, and more particularly to compositions for attracting male papaya mealybugs, compositions for disrupting male-female papaya mealybug mating, devices for trapping male papaya mealybugs, and methods for disrupting male-female papaya mealybug mating. [Background technology]

[0002] The papaya mealybug (Paracoccus marginatus) is a mealybug native to Central and South America that has spread worldwide as an invasive pest, and was confirmed to have become established on Okinawa Island in 2021. Its wide host range makes it a difficult-to-control pest, causing significant damage to tropical fruit trees such as papaya, banana, avocado, and guava, horticultural crops such as tomatoes and eggplant, and industrial crops such as cotton. Chemical pesticides are commonly used to control scale insects, but they pose problems such as the emergence of pesticide-resistant individuals, resurgence, environmental pollution, and residues on agricultural crops. Therefore, efficient control using minimal amounts of pesticides is desirable. To achieve this, it is necessary to accurately understand the abundance and timing of papaya mealybug infestations.

[0003] Traps that utilize attractants such as sex pheromones are used as a means of monitoring the occurrence of pest insects. Sex pheromones are chemical substances generally secreted by adult female insects, and they exhibit a species-specific and strong attractant effect on adult male insects of the same species. Therefore, if the chemical structure of sex pheromones could be clarified and they could be industrially synthesized and sex pheromone traps could be supplied, it would be possible to efficiently and easily investigate the occurrence of pest insects (Non-Patent Document 1). It is also known that sex pheromones can be used as mating disruptors (Non-Patent Document 2), and registration of these as pesticides is currently underway.

[0004] Sex pheromones of many pest species have already been identified and are being used in pest management as materials, including traps (for example, Patent Documents 1 and 2). Regarding mealybugs, sex pheromones of the two-striped mealybug, the sable mealybug, and the azalea mealybug have been identified (Patent Documents 3 to 5), but these chemical structures differ between species, and no chemical structure common to all mealybugs has been found, and there have been no reports on the sex pheromone of the papaya mealybug. [Prior art documents] [Patent documents]

[0005] [Patent Document 1] Patent No. 4734553 [Patent Document 2] Patent No. 5857369 [Patent Document 3] Japanese Patent Application Laid-Open No. 2017-197444 [Patent Document 4] Japanese Patent Application Laid-Open No. 2017-197446 [Patent Document 5] Japanese Patent Application Publication No. 2023-099930 [Non-patent literature]

[0006] [Non-Patent Document 1] Sawamura, N. et al., Predicting the emergence period of larvae of the persimmon mealybug (Hemiptera: Pseudococcidae) using sex pheromones and effective accumulated temperature, Journal of the Japanese Society of Applied Entomology and Zoology, Vol. 59, No. 4, 2015, pp. 183-189. https: / / doi.org / 10.1303 / jjaez.2015.183 [Non-patent document 2] Mayumi Teshiba et al., Mating disruption effect of sex pheromone components on the wisteria mealybug, Planococcus kraunhiae (Kuwana) (Hemiptera: Pseudococcidae), Journal of the Japanese Society of Applied Entomology and Zoology, Vol. 53, No. 4, 2009, pp. 173-180. https: / / doi.org / 10.1303 / jjaez.2009.173 Summary of the Invention [Problem to be solved by the invention]

[0007] If the sex pheromone or attractant of papaya mealybugs could be identified, it would be possible to efficiently monitor and control the papaya mealybugs. Therefore, an object of the present invention is to provide a composition capable of attracting papaya mealybugs. [Means for solving the problem]

[0008] As a result of extensive research aimed at solving the above problems, the present inventors have discovered that compounds having specific structures have the activity of attracting male papaya mealybugs, and have completed the present invention. That is, the present invention provides the following composition, trapping device, and method.

[0009] [A-1] Formula (1): [ka] (1) (wherein n is 1 to 2) 1. A composition for attracting male papaya mealybugs and / or disrupting male-female mating of papaya mealybugs, comprising the compound of formula (I). [A-2] Formula (2): [ka] (2) The composition according to [A-1], comprising a compound of the formula: [A-3] Formula (3): [ka] (3) The composition according to [A-1], comprising a compound of the formula: [A-4] The composition according to [A-1], which contains at least one compound selected from the group consisting of compounds of formula (1-1), compounds of formula (1-2), and compounds of formula (1-3). [ka] [ka] [ka] [A-5] The following formula: [ka] The composition according to [A-1], comprising a compound of the formula: [A-6] The composition described in any one of [A-1] to [A-5], further comprising another active ingredient that attracts scale insects and / or another active ingredient that disrupts mating between male and female scale insects. [A-7] Formula (1): [ka] (1) (wherein n is 1 to 2) A trapping device for male papaya mealybugs containing the compound. [A-8] Formula (2): [ka] (2) A capture device according to [A-7], comprising a compound of the formula: [A-9] Formula (3): [ka] (3) A capture device according to [A-7], comprising a compound of the formula: [A-10] The capture device according to [A-7], which contains at least one compound selected from the group consisting of compounds of formula (1-1), compounds of formula (1-2), and compounds of formula (1-3). [ka] [ka] [ka] [A-11] The following formula: [ka] A capture device according to [A-7], comprising a compound of the formula: [A-12] Formula (1): [ka] (1) (wherein n is 1 to 2) A method for disrupting male-female mating of papaya mealybugs, comprising the step of applying the compound of formula (I) to a location where papaya mealybugs inhabit or are suspected to inhabit. [A-13] Formula (2): [ka] (2) The method according to [A-12], comprising a step of applying the compound of formula (I) to a place where papaya mealybugs live or are suspected to live. [A-14] Formula (3): [ka] (3) The method according to [A-12], comprising a step of applying the compound of formula (I) to a place where papaya mealybugs live or are suspected to live. [A-15] The method according to [A-12], comprising a step of applying at least one compound selected from the group consisting of compounds of formula (1-1), compounds of formula (1-2), and compounds of formula (1-3) to a habitat or suspected habitat of papaya mealybugs. [ka] [ka] [ka] [A-16] The following formula: [ka] The method according to [A-12], comprising a step of applying the compound of formula (I) to a place where papaya mealybugs live or are suspected to live.

[0010] [B-1] Formula (1'): [ka] (1') 1. A composition for attracting male papaya mealybugs and / or disrupting male-female mating of papaya mealybugs, comprising the compound of formula (I). [B-2] The compound is [ka] The composition according to [B-1] above, having a structure represented by the following formula: [B-3] A composition described in [B-1] or [B-2], further containing other active ingredients that attract scale insects and / or other active ingredients that disrupt male-female communication of scale insects. [B-4] Formula (1'): [ka] (1') A trapping device for male papaya mealybugs containing the compound. [B-5] The compound is [ka] The capture device described in [B-4] above has a structure represented by the following formula: [B-6] Formula (1'): [ka] (1') A method for disrupting male-female mating of papaya mealybugs, comprising the step of applying the compound of formula (I) to a location where papaya mealybugs inhabit or are suspected to inhabit. [B-7] The compound is [ka] The method according to [B-6] above, wherein the compound has a structure represented by the formula: [Effects of the Invention]

[0011] According to the present invention, the compound of formula (1) can be used to attract male papaya mealybugs and disrupt the mating between male and female papaya mealybugs, thereby enabling efficient control of papaya mealybugs. According to the present invention, the compound of formula (1') can be used to attract male papaya mealybugs and disrupt the mating between male and female papaya mealybugs, thereby enabling efficient control of papaya mealybugs. DETAILED DESCRIPTION OF THE INVENTION

[0012] The present invention will now be described in further detail. The composition of the present invention comprises a compound of formula (1): [ka] (1) (wherein n is 1 to 2) and / or disrupting mating between male and female papaya mealybugs, the composition comprising the compound of formula (I). The composition of the present invention contains one or more compounds of formula (1). The compound is a sex pheromone released by unmated females of the papaya mealybug, a pest insect, or a stereoisomer or homolog thereof. The compound represented by formula (1) can be synthesized by any method commonly used in the art. The compound of formula (1) can be synthesized by known methods, for example, by referring to J. Chem. Soc. Perkin Trans., 1990, pp. 3221-3224.

[0013] Because the compound of formula (1) has the activity of attracting male papaya mealybugs, the composition of the present invention can be used to attract male papaya mealybugs. Therefore, the composition can be used for investigating the occurrence of papaya mealybugs or for attracting and trapping (or killing) them. Furthermore, if the sex pheromone released by female papaya mealybugs or its analogues is artificially filled in their habitat or suspected habitat, male papaya mealybugs will be unable to determine the true habitat of the female and will be unable to reach the female. Therefore, the composition of the present invention can also be used to disrupt mating between male and female papaya mealybugs. The composition of the present invention contains a compound of formula (1). The composition of the present invention may contain one type of compound of formula (1), or may contain two or more types of compounds of formula (1).

[0014] The composition of the present invention has the formula (2): [ka] (2) It is preferable that the composition of the present invention contains a compound represented by the formula (2). The compound represented by the formula (2) may be one type of compound or two or more types of compounds. In this case, the composition of the present invention may further contain a compound other than the compound represented by the formula (2) in addition to the compound represented by the formula (2).

[0015] The composition of the present invention has the formula (3): [ka] (3) It is preferable that the composition of the present invention contains a compound represented by the formula (3). The compound represented by the formula (3) may be one type of compound or two or more types of compounds. In this case, the composition of the present invention may further contain a compound other than the compound represented by the formula (3) in addition to the compound represented by the formula (3).

[0016] The composition of the present invention preferably contains at least one compound selected from the group consisting of compounds of formula (1-1), compounds of formula (1-2), and compounds of formula (1-3), and more preferably contains a compound of formula (1-1). [ka] [ka] [ka]

[0017] The composition of the present invention may contain one compound selected from the group consisting of compounds of formula (1-1), compounds of formula (1-2), and compounds of formula (1-3), or may contain two or more compounds. In this case, the composition of the present invention may further contain other compounds in addition to one compound selected from the group consisting of compounds of formula (1-1), compounds of formula (1-2), and compounds of formula (1-3). Examples of compounds of formula (1) other than compounds of formula (1-1), compounds of formula (1-2), and compounds of formula (1-3) include stereoisomers (e.g., optical isomers, geometric isomers) of compounds of formula (1-1) and stereoisomers (e.g., optical isomers, geometric isomers) of compounds of formula (1-2) or (1-3). Among these, optical isomers (enantiomers) are preferred. The composition of the present invention may contain a mixture of the compound of formula (1-1) and its optical isomer, a mixture of the compound of formula (1-2) and the compound of formula (1-3), or a combination of these mixtures. When a mixture of the compound of formula (1-1) and its optical isomers is contained, the ratio of the compound of formula (1-1) to its optical isomers is not particularly limited. The composition of the present invention may contain a racemate of the compound of formula (1-1) and its optical isomers. When a mixture of the compound of formula (1-2) and the compound of formula (1-3) is contained, the ratio of the compound of formula (1-2) to the compound of formula (1-3) is not particularly limited. The composition of the present invention may contain a racemate of the compound of formula (1-2) and the compound of formula (1-3).

[0018] The composition of the present invention also comprises a compound represented by formula (1'): [ka] (1') The compound is a sex pheromone released by unmated females of the papaya mealybug, a pest insect, or a stereoisomer thereof. The compound represented by formula (1') can be synthesized by any method commonly used in the art.

[0019] Because the compound of formula (1') functions as a sex pheromone released by female papaya mealybugs, the composition of the present invention can be used to attract male papaya mealybugs. Therefore, the composition can be used to investigate the occurrence of papaya mealybugs or to attract and capture (or kill) them. Furthermore, if the sex pheromone released by female papaya mealybugs or an analog thereof is artificially filled in their habitat or a suspected habitat, male papaya mealybugs will be unable to determine the female's true habitat and will be unable to reach the female. Therefore, the composition of the present invention can also be used to disrupt the communication between male and female papaya mealybugs.

[0020] In one embodiment, the compound may be a syn-isomer in which the isopropenyl group and the methyl group are located on the same side of the cyclobutane ring, and has the following formula: [ka] The compound may be 2-[(1S,2S)-1-methyl-2-isopropenylcyclobutyl]ethan-1-ol, i.e., (-)-fragranol, having the structure represented by the following formula: (-)-Fragranol is significantly more effective at attracting adult male papaya mealybugs than other stereoisomers.

[0021] In one embodiment, the composition of the present invention further comprises an organic solvent. The organic solvent may be any organic solvent commonly used in the art without particular limitation, and may be, for example, a hydrocarbon organic solvent such as pentane or hexane.

[0022] In one embodiment, the composition of the present invention is in the form of a solution or emulsion. The concentration of the compound in the composition of the present invention is not particularly limited as long as the desired effect is achieved, but for example, when the purpose is to investigate the occurrence of papaya mealybugs or to attract and capture (or attract and kill) them, the concentration may be about 0.001 to about 100.0 mg / mL, preferably about 0.1 to about 10 mg / mL. When the purpose is to disrupt mating between male and female papaya mealybugs, the concentration of the compound in the composition of the present invention may be, for example, about 0.1 to about 1000 mg / mL, preferably about 0.5 to about 500 mg / mL.

[0023] In one embodiment, the composition of the present invention is in the form of a sustained-release carrier impregnated with the compound. The sustained-release carrier may be any of those commonly used in the art without any particular limitation, and may be, for example, a container such as a cap (septum), a thin tube, a laminated bag, or a capsule made of a material having a release-controlling function, such as rubber, polyethylene, polypropylene, ethylene-vinyl acetate copolymer, or polyvinyl chloride, and is preferably a septum or thin tube made of rubber or polyethylene.

[0024] The amount of the compound impregnated per sustained release carrier is not particularly limited as long as the desired effect is achieved. For example, when the purpose is to investigate the occurrence of papaya mealybugs or to attract and capture (or kill) them, the amount is about 1 cm 3 The amount of the compound impregnated per sustained release carrier may be, for example, about 0.01 to about 1000 mg, and preferably about 0.1 to about 1 mg. When disrupting mating between male and female papaya mealybugs, the amount of the compound impregnated per sustained release carrier may be, for example, about 1.0 to about 1000 mg, and preferably about 50 to about 500 mg.

[0025] The slow-release carrier can be used in combination with (attached to) a trap for capturing pests. The trap can be any trap commonly used in the art, without any particular limitation. For example, the trap may be a sticky trap, a water trap, or a suction trap, and is preferably a sticky trap. The number of slow-release carriers attached to the trap is not particularly limited and may be adjusted appropriately depending on the size and purpose of use. For example, about 1 to about 10 slow-release carriers may be attached to the trap.

[0026] The composition of the present invention, particularly a composition in the form of a sustained-release carrier impregnated with the compound, may be installed outdoors. The installation density of the sustained-release carrier outdoors is not particularly limited. For example, when a single sustained-release carrier is attached to a trap for the purpose of investigating the occurrence of papaya mealybugs or attracting and capturing (or killing) them, the installation density may be about 1 to about 1,000 sustained-release carriers per 10 ares, preferably about 10 to about 500 sustained-release carriers. The spacing between the sustained-release carriers is not particularly limited. For example, the spacing may be about 1 to about 100 m, preferably about 5 to about 15 m. When disrupting male-female communication in papaya mealybugs, the installation density of the sustained-release carriers outdoors may be, for example, about 50 to about 500 sustained-release carriers per 10 ares, and the spacing between the sustained-release carriers may be, for example, about 0.5 to 100 m, preferably about 1.4 to about 10 m.

[0027] The installation location of the composition of the present invention, particularly the composition in the form of the compound impregnated in the sustained-release carrier, is not particularly limited, and may be, for example, at a height of about 10 to about 200 cm, preferably about 30 to about 160 cm, above the ground. The installation timing of the composition is also not particularly limited, and may be, for example, during the adult emergence period of papaya mealybugs.

[0028] In one embodiment, the composition of the present invention is in the form of an agricultural or horticultural material, such as a net or rope, impregnated with the compound. The material impregnated with the compound is particularly useful for disrupting mating between male and female papaya mealybugs when widely installed in a field. The method for impregnating the material is not particularly limited, and for example, the compound may be impregnated by spraying or applying it in solution. The amount of the compound to be sprayed or applied is not particularly limited as long as the desired effect is achieved. For example, when disrupting mating between male and female papaya mealybugs, the amount of the compound impregnated into the material when installed in a field may be about 2.5 to about 250 g per 10 ares.

[0029] The composition of the present invention may further contain any excipients and / or additives commonly used in the art, as long as they do not impair the objectives of the present invention, and may further contain other active ingredients that attract scale insects or other active ingredients that disrupt mating between male and female scale insects.

[0030] In another aspect, the present invention relates to a trapping device for male papaya mealybugs, comprising the compound of formula (1) or formula (1'). The trapping device can be used for investigating the occurrence of papaya mealybugs or for attracting and capturing (or killing) them. In one aspect, the trapping device of the present invention may further comprise the sustained-release carrier and / or the trap. The trapping device of the present invention is not particularly limited, and may be used, for example, in the same manner as the composition in the form of a sustained-release carrier impregnated with the compound, as described above as one aspect of the present invention.

[0031] In another aspect, the present invention also relates to a method for disrupting male-female mating of papaya mealybugs, comprising the step of applying the compound of formula (1) or the compound of formula (1') to a location where papaya mealybugs inhabit or are suspected to inhabit. The method for applying the compound is not particularly limited, and for example, the compound may be diluted in a solvent capable of uniformly dispersing the compound and sprayed onto the target location, or the compound may be impregnated into the aforementioned sustained-release carrier or the aforementioned agricultural or horticultural material and then placed at the target location. That is, the compound may be applied in the same manner as the use of the composition in the form of a solution or emulsion, the form in which the compound is impregnated into a sustained-release carrier, or the form in which the compound is impregnated into agricultural or horticultural material, as described above as one aspect of the present invention.

[0032] The present invention will be specifically explained below with reference to examples, but the scope of the present invention is not limited to these examples. [Example]

[0033] 1. Isolation of a substance that attracts male papaya mealybugs One hundred eighty-nine virgin female adult papaya mealybugs were infested on germinated broad beans and sealed in a 0.2-liter glass container. Volatile compounds, including sex attractants, released into the air were then aspirated using an air pump (flow rate set at approximately 100 mL / min) for 2 days and collected with 100 mg of adsorbent (Haysep Q, mesh size 60-80; GL Sciences) 10 times.

[0034] All volatile compounds captured by the adsorbent were eluted with approximately 3 mL of hexane to obtain a crude extract. This crude extract was concentrated to approximately 0.03 mL using a rotary evaporator and injected into a column chromatograph packed with 0.2 g of silica gel. The extract was then fractionated and eluted with 2 mL, 3 mL, 8 mL, and 8 mL of hexane containing 0%, 5%, 15%, or 50% diethyl ether, respectively. One female equivalent (i.e., the amount of pheromone released by one female per day) of each eluate was applied to a 1 cm square filter paper and placed in a 9 cm diameter Petri dish containing adult males. Only the eluate containing 15% diethyl ether in hexane exhibited attractant activity.

[0035] The fractions showing this attractant activity were further fractionated using a high-performance liquid chromatograph equipped with an Inertsil SIL 100A column (5 μm particle size, 4.6 mm internal diameter, 250 mm length; GL Sciences). Hexane containing 30% diethyl ether was applied at a flow rate of 1 mL / min, and the attractant activity of each eluted fraction was examined in the same manner as for the column chromatography extract. The attractant activity was observed in the fraction eluted between 14 and 16 minutes of retention time.

[0036] The fraction with a retention time of 14 to 16 minutes was further fractionated using a gas chromatograph (Agilent) equipped with a DB-23 column (0.53 mm internal diameter, 15 m length). The temperature inside the column oven was raised from an initial temperature of 60°C (held for 5 minutes) to 200°C at a rate of 10°C per minute. To separate the substance eluting at 14.0 minutes (compound X) from the other components, the fractions eluted from approximately 13.8 minutes after injection into the system, from approximately 13.8 minutes to approximately 14.2 minutes after injection, and from approximately 14.2 minutes to the end of injection were collected. Hexane solutions of each compound were prepared, and their attractant activity was examined in the same manner as for the column chromatography extract. Only the hexane solution containing compound X exhibited attractant activity.

[0037] 2. Analysis of Isolated Compounds Compound X was analyzed using a mass spectrometer (Agilent). The molecular ion was determined to be 154, and the molecular formula was C 10 H 18 The EI mass spectrum [m / z (relative intensity %)] is as follows: 41 (16.5), 53 (14.6), 55 (10.0), 56 (13.0), 67 (68.9), 68 (100, base ion), 69 (17.1), 77 (6.5), 79 (9.1), 81 (9.9), 85 (5.8), 91 (6.7), 93 (14.5), 107 (14.6), 108 (14.4), 109 (49.5), 110 (6.7), 111 (14.9), 121 (12.5), 154 (0.1)

[0038] Furthermore, Compound X was analyzed using a nuclear magnetic resonance (NMR) spectrometer (manufactured by JEOL Ltd.). 1 H-NMR and 13 The measured values ​​of C-NMR are as follows: δH: 5.01 (d, J = 1.4 Hz, 1H), 4.82 (br s, 1H), 3.49-3.46 (m, 2H), 2.54 (t, J = 8.9 Hz, 1H), 2.07-2.00 (m, 1H), 1.86-1.82 (m, 1H), 1.79-1.74 (m, 1H), 1.67-1.58 (m, 2H), 1.66 (s, 3H), 1.42-1.39 (m, 1H), 0.98 (s, 3H);δC: 145.6, 110.0, 59.5, 50.7, 46.8, 41.1, 30.4, 23.1, 20.0, 19.6.

[0039] The mass spectrum and NMR spectrum of compound X were determined by a compound of formula (1'): [ka] (1') The spectrum of this compound matched that of the racemic mixture of the 1S,2S and 1R,2R isomers (syn isomers in which the isopropenyl and methyl groups are located on the same side of the cyclobutane ring).

[0040] To clarify the configuration of compound X, further analysis was performed using a high-performance liquid chromatograph equipped with a Chiralpak IG column (particle size 5 μm, internal diameter 4.6 mm, length 250 mm; Daicel Corporation). Using hexane containing 1.5% ethanol as the eluent at a flow rate of 1 mL / min, the retention time of compound X was 13.5 minutes, which coincided with the retention time of authentic (-)-fragranol, i.e., the (1S,2S) form. Therefore, compound X was shown to be (-)-2-[(1S,2S)-1-methyl-2-isopropenylcyclobutyl]ethan-1-ol, which has the following chemical structure: [ka]

[0041] 3. Attraction test of adult male papaya mealybugs A rubber septum was impregnated with 0.1 mL of either plain hexane or a hexane solution containing 1 mg / mL of Compound X. A trapping device was then created by attaching one of the rubber septa to a small, commercially available adhesive board (10 cm x 20 cm) as an attractant. These were placed around wild-growing papayas and left there from August 8 to 18, 2023, and the number of adult male papaya mealybugs captured was counted.

[0042] As a result, an average of 43.3 adult male papaya mealybugs were captured per day during the test period on sticky boards equipped with rubber septa containing Compound X as an attractant. On sticky boards equipped with rubber septa not containing Compound X as an attractant, an average of less than 0.1 adult male papaya mealybugs were captured per day, and a significant difference was observed between the numbers captured on both boards (likelihood ratio test: P value < 0.0001).

[0043] From the above, it was found that the compound of formula (1') has an effect of attracting male papaya mealybugs. Therefore, the compound of formula (1') can be used to capture male papaya mealybugs or to disrupt the communication between male and female papaya mealybugs.

[0044] 4. Attractant activity test of sex pheromone homologs Next, we investigated whether homologs of the sex pheromone compound Compound X also have the ability to attract male papaya mealybugs. Specifically, we produced compounds with one fewer carbon atom in the alcohol group than Sex pheromone Compound X, and examined whether these compounds had the ability to attract male papaya mealybugs. Compound X was synthesized by a known method and represented by formula (2): [ka] (2) The racemates of the 1S,2S and 1R,2R isomers (syn isomers in which the isopropenyl and methyl groups are located on the same side of the cyclobutane ring) of compound X were separated by high-performance liquid chromatography equipped with an enantiomer separation column [Chiralpak IG (4.6 x 250 mm, particle size 5 μm)] using a hexane:ethanol mixture (volume ratio 100:1.5) at a flow rate of 1 ml / min. The retention time of compound X, i.e., compound (1-1), was 13.5 min. [ka]

[0045] Next, compounds (1-2) and (1-3), each having one carbon atom less in the alcohol group than sex pheromone compound X, were synthesized by a known method to obtain compound (3): [ka] (3) The racemates of the 1S,2S and 1R,2R isomers (syn isomers in which the isopropenyl and methyl groups are located on the same side of the cyclobutane ring) of compound (1-2) were obtained by elution at a flow rate of 1 ml / min using a hexane:ethanol mixture (volume ratio 100:1.5) on a high-performance liquid chromatography column equipped with a Chiralpak IG (4.6 x 250 mm, 5 μm particle size). The retention times of compounds (1-2) and (1-3) were 13.7 and 10.9 min, respectively. [ka] [ka]

[0046] The sex pheromone compound (1-1) and its homologues (1-2) and (1-3) were investigated for their attractiveness to adult males of the papaya mealybug. A rubber septum was impregnated with 0.1 mL of a hexane solution containing 1 mg / mL of compound (1-1), compound (1-2), or compound (1-3), or a hexane solution (control) containing no of these compounds. One rubber septum was then attached to a commercially available small adhesive board (10 cm x 20 cm) as an attractant to create a trapping device. These were placed near papaya or trifoliate daisies growing in the field where papaya mealybug infestations had been confirmed, and left there from August 6 to 8, 2024, and the number of papaya mealybugs captured was counted. Two rubber septa containing compounds (1-1) to (1-3) or a control were prepared and placed around one papaya tree at intervals of at least 1 m. The height at which the rubber septa were placed was approximately 1.3 meters. To eliminate the influence of differences in the distance from the papaya to each rubber septum, the placement positions of each rubber septum were randomly rotated every other day. Similarly, one rubber septum containing compounds (1-1) to (2-2) or a control was prepared and placed around each of two Tithonia sieboldii plants at intervals of at least 1 m. The height at which the rubber septa were placed was approximately 1.3 meters. To eliminate the influence of differences in the distance from the Tithonia sieboldii to each rubber septum, the placement positions of each rubber septum were randomly rotated every other day. Table 1 shows the average number of papaya mealybugs trapped per day per rubber septum containing compounds (1-1) to (1-3) or a control placed around papayas and titmice.

[0047] [Table 1]

[0048] As a result of the test, sticky boards equipped with rubber septa containing compound (1-2) or compound (1-3), which are homologs of the sex pheromone compound (1-1), captured an average of 5.3 and 13.8 adult male papaya mealybugs per day during the test period, respectively. On the other hand, sticky boards equipped with control rubber septa captured an average of less than 0.3 per day. A significant difference (likelihood ratio test: P value < 0.001) was observed between the number of captures when compound (1-2) or compound (1-3) was contained and the number of captures when the control was used.

[0049] From the above, it was found that the compounds of formulas (1-2) and (1-3), which are homologues of the sex pheromone compound, have the effect of attracting male papaya mealybugs, although their activity is weaker than that of the sex pheromone compound (1-1). Therefore, it was confirmed that the above compounds can be used to capture male papaya mealybugs or to disrupt mating between male and female papaya mealybugs.

Claims

1. Formula (1): 【Chemical 1】 （１） (wherein n is 1 to 2) 2. A composition for attracting male papaya mealybugs and / or disrupting male-female mating of papaya mealybugs, comprising the compound of formula (I).

2. Formula (2): 【Chemistry 2】 （２） 10. The composition of claim 1, comprising a compound of formula:

3. Formula (3): 【Chemistry 3】 （３） 10. The composition of claim 1, comprising a compound of formula:

4. The composition according to claim 1, comprising at least one compound selected from the group consisting of compounds of formula (1-1), compounds of formula (1-2), and compounds of formula (1-3). 【Chemistry 4】 【Chemistry 5】 【Chemistry 6】

5. The following formula: 【Chemistry 7】 10. The composition of claim 1, comprising a compound of formula:

6. The composition according to any one of claims 1 to 5, further comprising another active ingredient that attracts scale insects and / or another active ingredient that disrupts mating between male and female scale insects.

7. Formula (1): 【Chemistry 8】 （１） (wherein n is 1 to 2) A trapping device for male papaya mealybugs containing the compound.

8. Formula (2): 【Chemistry 9】 （２） 8. The capture device of claim 7, comprising a compound of formula:

9. Formula (3): 【Chemistry 10】 （３） 8. The capture device of claim 7, comprising a compound of formula:

10. 8. The capture device according to claim 7, comprising at least one compound selected from the group consisting of compounds of formula (1-1), compounds of formula (1-2), and compounds of formula (1-3). 【Chemistry 11】 【Chemistry 12】 【Chemistry 13】

11. The following formula: 【Chemistry 14】 8. The capture device of claim 7, comprising a compound of formula:

12. Formula (1): 【Chemistry 15】 （１） (wherein n is 1 to 2) A method for disrupting male-female mating of papaya mealybugs, comprising the step of applying the compound of formula (I) to a location where papaya mealybugs inhabit or are suspected to inhabit.

13. Formula (2): 【Chemistry 16】 （２） 13. The method of claim 12, comprising the step of applying a compound of formula (I) to a locus or suspected locus of papaya mealybug.

14. Formula (3): 【Chemistry 17】 （３） 13. The method of claim 12, comprising the step of applying a compound of formula (I) to a locus or suspected locus of papaya mealybug.

15. The method according to claim 12, comprising a step of applying at least one compound selected from the group consisting of the compound of formula (1-1), the compound of formula (1-2), and the compound of formula (1-3) to a location where papaya mealybugs live or are suspected to live. 【Chemistry 18】 【Chemistry 19】 【Chemistry 20】

16. The following formula: 【Chemical 21】 13. The method of claim 12, comprising the step of applying a compound of formula (I) to a locus or suspected locus of papaya mealybug.

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