Composition physiologically active to setothosea asigna, sustained release preparation for controlling including the same, and method of controlling

Abstract

To provide an economical composition capable of continuing attraction of Setothosea asigna for a long period of time.SOLUTION: There is provided a composition at least including 100 pts.mass of (9E)-9-dodecenal, 1 to 40 pts.mass of (9Z)-9-dodecenal, and 1 to 70 pts.mass of (9E)-9,11-dodecadienal. There is provided a sustained release preparation for controlling Setothosea asigna at least including the composition, and a carrier or a container for carrying or housing the composition and sustainedly releasing at least the (9E)-9-dodecenal, the (9Z)-9-dodecenal and the (9E)-9,11-dodecadienal. There is provided a method of controlling Setothosea asigna at least including a step of setting the sustained release preparation in a field, and releasing at least the (9E)-9-dodecenal, the (9Z)-9-dodecenal and the (9E)-9,11-dodecadienal.SELECTED DRAWING: None

Description

[Technical field]

[0001] The present invention relates to Setothosea asigna The present invention relates to a composition that is physiologically active against and a sustained-release formulation for control containing the same. [Background technology]

[0002] Nettle caterpillar (scientific name: Setothosea asigna (Hereinafter referred to as this scientific name) is a serious pest of oil palm in Southeast Asia, including Indonesia and Malaysia. The damage caused by this pest to palm leaves significantly reduces the yield of oil palm, and is therefore a major problem in plantations. Furthermore, from the standpoint of reducing the environmental impact and managing the health of plantation workers, there are limitations on the insecticides that can be used, making effective control difficult. In recent years, therefore, biological control methods have been attracting attention, and one promising method is the use of sex pheromone substances.

[0003] Control methods that use sex pheromone substances include the mass trapping or attract and kill method, which uses a pheromone attractant to attract adult insects, gather them in a certain place, and capture (kill) them to reduce the pest density in the field; the push-pull method, which uses a pheromone attractant and a repellent to move pests in a certain direction and capture (kill) them to reduce the pest density in the field; the attract and infect method, which uses a pheromone attractant to attract adult insects, infects them with a pathogen, and releases them into the field to infect the target pests with the pathogen, thereby reducing the pest density; and the mating disruption method, which uses a pheromone agent to prevent them from finding a mating partner in the field, thereby reducing the pest density of the next generation (Non-Patent Document 1). In any of the above control methods, it is important to have an attractant composition that can strongly attract the target pest for a long period of time.

[0004] Setothosea asigna The results of pheromone gland extraction and GC-EAD (GC-electroantennographic detection: gas chromatography with antenna potential detector) analysis showed that Setothosea asigna It has been reported that the pheromone candidate compounds are seven types of compounds, namely 10-undecenal, dodecanal, (9E)-9-dodecenal, (9Z)-9-dodecenal, (9E)-9-dodecenol, (9E)-9,11-dodecadienal and (9E)-9,11-dodecadienol (Non-Patent Document 2). Furthermore, in a field attraction test, it was found that when a mixture composition of (9E)-9-dodecenal and (9E)-9,11-dodecadienal in a mass ratio of 100:100 (i.e., a mixture composition containing equal amounts of each component) was used, Setothosea asigna On the other hand, when a mixture composition of (9E)-9-dodecenal and (9E)-9,11-dodecadienal in a mass ratio of 100:10 was used, Setothosea asigna It was revealed that the pheromone candidate compounds other than (9E)-9-dodecenal and (9E)-9,11-dodecadienal were not essential for attraction in the tests in the literature, and no effect of enhancing attraction was observed. Therefore, it was concluded that only (9E)-9-dodecenal and (9E)-9,11-dodecadienal were essential for attraction. Setothosea asigna It has been identified as the sex pheromone of the insect (Non-Patent Document 2).

[0005] In this way, Setothosea asigna It has been reported that the sex pheromone of this insect is a mixture of (9E)-9-dodecenal and (9E)-9,11-dodecadienal, which is a terminally conjugated alkadienal compound, and it has been suggested that (9Z)-9-dodecenal is an inactive component (Non-Patent Document 2). Here, (9Z)-9-dodecenal is a geometric isomer of (9E)-9-dodecenal, Setothosea asigna Related species of Setora nitensIt is the sex pheromone of the insect (Non-Patent Document 3).

[0006] By the way, whether compounds with a structure similar to a pheromone substance have the same effect as the pheromone substance varies from insect to insect, and it has been reported that there are cases where the compound acts as an inhibitor. For example, in the case of the Tomato fruit borer, a pest of tomatoes in South America, Neoleucinodes elegantalis In the case of the sex pheromone of the male, (11E)-11-hexadecenol is the main sex pheromone component and (3Z,6Z,9Z)-3,6,9-tricosatriene is the minor sex pheromone component, and it has been reported that the addition of (11Z)-11-hexadecenol, which is a geometric isomer of the main sex pheromone component (11E)-11-hexadecenol, significantly reduces the attractant number (Non-Patent Document 4). [Prior art documents] [Non-patent literature]

[0007] [Non-Patent Document 1] BSHansson (Ed.), Insect Olfaction, Chapter 12 “Applied Aspects of Insect Olfaction”, 1999, 352-377. [Non-Patent Document 2] Yorianta Sasaerila et al., J.Chem.Ecol.,1997,23(9):2187-2196. [Non-Patent Document 3] Yorianta Sasaerila et al., J.Chem.Ecol.,2000,26(8):1983-1990. [Non-Patent Document 4] Aivle Cabrera, J.Chem.Ecol.,2001,27(10),2097. Summary of the Invention [Problem to be solved by the invention]

[0008] According to Experiments 1, 2, 7 and 8 in Figure 3 of Non-Patent Document 2, among the many attractant compositions used in the field test, the mixture composition of (9E)-9-dodecenal and (9E)-9,11-dodecadienal in a mass ratio of 100:100 (i.e., a mixture composition containing equal amounts of each component) was the most active as a physiologically active component, and although the attractant activity against males was confirmed, the number of attractants was extremely small, at a maximum of 5 in a test over 3 to 15 days, and the attractant activity and the attractiveness evaluation test itself could not be said to be sufficient. Furthermore, as the authors also state, a major issue was that the sex pheromone components were decomposed by the effects of ultraviolet light and oxygen in the air, making it impossible to maintain the attraction for a long period of time. This is thought to be because a large amount of (9E)-9,11-dodecadienal, which is less stable and more likely to polymerize, is used, causing the (9E)-9,11-dodecadienal to polymerize on the surface of the formulation, disrupting the composition ratio of the pheromone released from the agent, or because a polymer film is formed on the agent, making it difficult to release the volatile pheromone compound itself.

[0009] Setothosea asigna Since insects can occur throughout the year in Southeast Asia, attractant compositions that are only effective for a short period of time must be frequently renewed, which requires a great deal of effort. Furthermore, attractant compositions that are only effective for a short period of time may run out of life during use and not attract insects, making it difficult to accurately grasp the occurrence and growth of insect populations, and sometimes causing severe agricultural damage due to missed timing for control. In addition, the terminal alkadienal compound (9E)-9,11-dodecadienal, which is more expensive than (9E)-9-dodecenal because it is more difficult to manufacture, must be used in an amount equivalent to that of (9E)-9-dodecenal, which poses major problems from an economic standpoint when put to practical use. For this reason, in order to put attractant compositions to practical use, Setothosea asigna Considering the severity of the agricultural damage caused by these insects, there has been a strong demand for economical attractant compositions and formulations that can be used for a long period of time.

[0010] In order to maintain long-term release, it is desirable to reduce the amount of (9E)-9,11-dodecadienal, which is an unstable compound, as described above. That is, by increasing the amount of the more stable (9E)-9-dodecenal, the unstable (9E)-9,11-dodecadienal is diluted and stabilized by (9E)-9-dodecenal, which is considered to prevent polymerization and the formation of a polymer membrane, thereby maintaining long-term release. However, as described in Non-Patent Document 2, when the ratio of (9E)-9,11-dodecadienal to (9E)-9-dodecenal decreases, the attractive force itself decreases, and the target attractive ability cannot be maintained, which is a problem.

[0011] The present invention has been made in consideration of the above circumstances, Setothosea asigna The present invention aims to provide an economical composition capable of continuing to attract insects for a long period of time, a controlled release formulation for pest control using said composition, and a control method. [Means for solving the problem]

[0012] In order to solve the above problems, the present inventors Setothosea asigna As a result of conducting an attraction test, Setothosea asigna By adding (9Z)-9-dodecenal, which is a sex pheromone of a related species and can be produced inexpensively, even when the ratio of (9E)-9-dodecenal to (9E)-9-dodecenal is reduced, that is, even when a mixture of (9E)-9-dodecenal and (9E)-9,11-dodecadienal has a mass ratio of 100:1 to 100:70, Setothosea asigna It was found that the composition has sufficient attraction to the insects, and that the attraction can be further improved. In other words, it was found that a certain amount of (9Z)-9-dodecenal is a component that can enhance attraction. Furthermore, it was found that the sustained release formulation produced from this composition can be used for a long period of time and has an extremely excellent attractant ability, which led to the present invention.

[0013] According to one embodiment of the present invention, there is provided a composition comprising at least 100 parts by mass of (9E)-9-dodecenal, 1 to 40 parts by mass of (9Z)-9-dodecenal, and 1 to 70 parts by mass of (9E)-9,11-dodecadienal. In another aspect of the present invention, a method for producing a pharmaceutical composition comprising the composition, a carrier or container for carrying or containing the composition and releasing at least the (9E)-9-dodecenal, the (9Z)-9-dodecenal, and the (9E)-9,11-dodecadienal, is provided. Setothosea asigna Control sustained release formulations are provided. In yet another aspect of the present invention, the method includes at least a step of placing the sustained release formulation in a field and releasing at least the (9E)-9-dodecenal, the (9Z)-9-dodecenal, and the (9E)-9,11-dodecadienal into the field. Setothosea asigna A method for controlling the pests is provided. Effect of the Invention

[0014] According to the present invention, more Setothosea asigna It is possible to obtain an effective and economical composition that specifically attracts male adults of this species and allows for more detailed information on the occurrence of this species. In addition, by using the composition to prepare a sustained release formulation, it is possible to directly control this species by applying it to mass trapping and mating disruption, etc. [Brief description of the drawings]

[0015]

Figure 1

Figure 2

Figure 3

Figure 4

[0016] First, a composition containing at least (9E)-9-dodecenal (1), (9E)-9,11-dodecadienal (3) and (9Z)-9-dodecenal (2) will be described. This composition is Setothosea asigna In order to facilitate the identification of these three compounds, the names of the compounds are followed by the symbols (1), (2), and (3), which represent Compound 1, Compound 2, and Compound 3, respectively. As mentioned above, only these two types of (9E)-9-dodecenal (1) and (9E)-9,11-dodecadienal (3) can be synthesized. Setothosea asigna (Non-Patent Document 2). Therefore, a composition containing (9E)-9-dodecenal (1) or (9E)-9,11-dodecadienal (3) is Setothosea asigna It has biological activity against

[0017] (9Z)-9-dodecenal (2) is a geometric isomer of (9E)-9-dodecenal (1), and as described above, Setothosea asigna Related species of Setora nitens (9Z)-9-dodecenal (2) is a sex pheromone of Setothosea asigna However, there have been no reports to date that it enhances the attractant ability of mosquitoes, and as mentioned above, it has been suggested that it is an inactive ingredient (Non-Patent Document 2). Furthermore, as mentioned above, whether compounds with a structure similar to a pheromone substance have the same effect as the pheromone substance varies from insect to insect, and it has been reported that in some cases they can even act as an inhibitor. The effects of insect sex pheromone-related compounds and geometric isomers on attraction vary from insect to insect, so it is necessary to conduct actual attraction tests to confirm. More generally, if an insect is attracted to the sex pheromones of a related species that may exist sympatric, there is a high possibility that it will be selected out through hybridization, so it is quite likely that in the course of evolution it will evolve to repel the sex pheromones of related species. Therefore, Setothosea asigna In this case, related species may exist sympatric Setora nitens It was initially not thought that the sex pheromone, (9Z)-9-dodecenal (2), of the insect, would enhance attraction.

[0018] (9E)-9-dodecenal (1), (9E)-9,11-dodecadienal (3), and (9Z)-9-dodecenal (2) may be natural extracts of sex pheromones, etc., but from an economical point of view, they are preferably artificially synthesized compounds.

[0019] (9E)-9-dodecenal (1) can be produced, for example, as described in JP 2023-025200 A, by a method including at least a step of converting a (3E)-11-halo-3-undecene compound into an (8E)-8-undecenyl nucleophile, followed by a nucleophilic addition reaction with an orthoformate to obtain a (9E)-1,1-dialkoxy-9-dodecene compound, and a step of hydrolyzing the obtained (9E)-1,1-dialkoxy-9-dodecene compound.

[0020] (9Z)-9-dodecenal (2) can be produced, for example, as described in JP 2023-025200 A, by a method including at least a step of converting a (3Z)-11-halo-3-undecene compound into an (8Z)-8-undecenyl nucleophile, followed by a nucleophilic addition reaction with an orthoformate to obtain a (9Z)-1,1-dialkoxy-9-dodecene compound, and a step of hydrolyzing the obtained (9Z)-1,1-dialkoxy-9-dodecene compound.

[0021] (9E)-9,11-dodecadienal (3) can be produced, for example, as described in JP 2022-060174 A, by a method including at least a step of obtaining a (3E)-12,12-dialkoxy-1,3-dodecadiene compound from a (3E)-1-halo-12,12-dialkoxy-3-dodecene compound by a base-induced elimination reaction, and a step of hydrolyzing the obtained (3E)-12,12-dialkoxy-1,3-dodecadiene compound.

[0022] The mixing ratio (1):(2):(3) of (9E)-9-dodecenal (1), (9Z)-9-dodecenal (2) and (9E)-9,11-dodecadienal (3) is not particularly limited as long as it is within the range in which male adult insects are attracted. Specifically, the mixing ratio is 1 to 70 parts by mass of (9E)-9,11-dodecadienal (3) when the mixing ratio of (9Z)-9-dodecenal (2) is 1 to 40 parts by mass relative to 100 parts by mass of (9E)-9-dodecenal (1). From the viewpoint of attractant activity, the amount of (9Z)-9-dodecenal (2) added is 1 to 40 parts by mass, preferably 1 to 35 parts by mass, more preferably 1 to 30 parts by mass, even more preferably 10 to 30 parts by mass, and particularly preferably 25 to 30 parts by mass, relative to 100 parts by mass of (9E)-9-dodecenal (1). However, depending on the amount of (9E)-9,11-dodecadienal (3) added, 1 to 5 parts by mass may be particularly preferred. From the viewpoint of attractant activity and release stability, the amount of (9E)-9,11-dodecadienal (3) added is 1 to 70 parts by mass, preferably 5 to 70 parts by mass, more preferably 10 to 70 parts by mass, even more preferably 10 to 50 parts by mass, and particularly preferably 25 to 35 parts by mass, relative to 100 parts by mass of (9E)-9-dodecenal (1). However, depending on the amount of (9Z)-9-dodecenal (2) added, 5 to 15 parts by mass may be particularly preferred.

[0023] The combination of (9E)-9-dodecenal (1), (9Z)-9-dodecenal (2) and (9E)-9,11-dodecadienal (3) in the mixing ratio (1):(2):(3) is as follows: (9E)-9-dodecenal (1): per 100 parts by mass (9Z)-9-dodecenal (2): 1 to 40 parts by mass, (9E)-9,11-dodecadienal (3): 1 to 70 parts by mass; A preferred combination is: (9E)-9-dodecenal (1): per 100 parts by mass (9Z)-9-dodecenal (2): 1 to 35 parts by mass, (9E)-9,11-dodecadienal (3): 5 to 70 parts by mass; More preferred combinations include: (9E)-9-dodecenal (1): per 100 parts by mass (9Z)-9-dodecenal (2): 1 to 30 parts by mass, (9E)-9,11-dodecadienal (3): 10 to 70 parts by mass; More preferred combinations include: (9E)-9-dodecenal (1): per 100 parts by mass (9Z)-9-dodecenal (2): 10 to 30 parts by mass, (9E)-9,11-dodecadienal (3): 20 to 70 parts by mass; Particularly preferred combinations include: (9E)-9-dodecenal (1): per 100 parts by mass (9Z)-9-dodecenal (2): 1 to 5 parts by mass, (9E)-9,11-dodecadienal (3): 25 to 35 parts by mass; or (9E)-9-dodecenal (1): per 100 parts by mass (9Z)-9-dodecenal (2): 25 to 30 parts by mass (9E)-9,11-dodecadienal (3): 5 to 15 parts by mass. (9E)-9-dodecenal (1), (9Z)-9-dodecenal (2), and (9E)-9,11-dodecadienal (3) may contain impurities that are unavoidable in the production process.

[0024] The bioactive composition may contain additives such as antioxidants and ultraviolet absorbers. Examples of antioxidants include 2,6-di-tert-butyl-4-methylphenol (BHT), 4,4'-butylidenebis(6-tert-butyl-m-cresol) (BBMTBP), 2,2'-methylenebis(4-methyl-6-tert-butylphenol) (MBMTBP), 2,2'-methylenebis(4-ethyl-6-tert-butylphenol), butylhydroxytoluene, butylhydroxyanisole, hydroquinone, vitamin E, and the like. Examples of ultraviolet absorbers include 2-hydroxy-4-octyloxybenzophenone and 2-(2'-hydroxy-3'-tert-butyl-5'-methylphenyl)-5-chlorobenzotriazole (HBMCBT). When the physiologically active composition is used in a sustained release formulation, the additive may be a compound that is released together with (9E)-9-dodecenal (1), (9Z)-9-dodecenal (2), and (9E)-9,11-dodecadienal (3), or may be a compound that remains without being released. The content of each additive in the physiologically active composition is, for example, preferably 0.5 to 50 mass% for the antioxidant and preferably 0.5 to 50 mass% for the ultraviolet absorber relative to the total amount of (9E)-9-dodecenal (1), (9Z)-9-dodecenal (2), and (9E)-9,11-dodecadienal (3).

[0025] Next, the sustained release preparation at least includes the physiologically active composition and a carrier or container for carrying or storing the physiologically active composition and releasing at least the (9E)-9-dodecenal (1), (9Z)-9-dodecenal (2) and (9E)-9,11-dodecadienal (3) will be described. The release is preferably sustained release because it is a sustained release preparation. The release of (9E)-9-dodecenal (1), (9Z)-9-dodecenal (2), and (9E)-9,11-dodecadienal (3) into a field is not particularly limited as long as it can control the pests. For example, the release can be carried out using a sustained-release preparation comprising a carrier impregnated with the physiologically active composition, or a sustained-release preparation comprising a container such as a cap, tube, capsule, beads, bottle, ampule, can, or bag containing the physiologically active composition.

[0026] The sustained-release formulation may be any formulation that can release an active ingredient such as a pheromone compound from a carrier or container in small amounts at regular or irregular intervals for a desired period of time for pest control or other purposes, and examples of such formulations include lure formulations, reservoir-type formulations, matrix formulations, aerosol formulations, and spray-type formulations. The desired period of time depends on the climate and region, etc. Setothosea asigna Taking into consideration the period during which the disease occurs, for example, a period of 2 to 3 months is used for the application of a formulation once, and a period of 5 to 6 months is used for the application of a formulation twice. At this time, it is sufficient that the active ingredient such as a pheromone compound can be released, for example, into a field, regardless of whether it is released actively or passively from a carrier or a container.

[0027] Setothosea asigna The controlled release formulation comprises the physiologically active composition and a carrier or container for carrying or storing the physiologically active composition and releasing at least (9E)-9-dodecenal (1), (9Z)-9-dodecenal (2), and (9E)-9,11-dodecadienal (3) in the physiologically active composition. The sustained release preparation comprising a carrier can be manufactured by known techniques, such as kneading or impregnation into the carrier. The shape and size of the carrier vary depending on the application method and application amount. For example, in the case of a hand-applied preparation comprising a ring-shaped carrier, the ring diameter is preferably 0.01 to 5 m, and in the case of a spray preparation comprising a granular carrier having a spherical or elliptical shape, the diameter of the particle (long side in the case of an ellipse) is preferably 0.01 to 10 cm. The amount of the carrier to be supported varies depending on the application method and application amount, but is preferably 0.01 mg to 100 g, more preferably 1 mg to 10 g per preparation.

[0028] The sustained-release preparation equipped with a container can be produced by known techniques, for example, a method of injecting the physiologically active composition or the like into a polymeric tubular container and sealing both ends of the tube, or a method of filling the physiologically active composition or the like into a can and attaching a valve capable of spraying.

[0029] A diluent may be used as necessary for the sustained release formulation provided with a container. Examples of diluents include hydrocarbons such as hexane, heptane, octane, nonane, decane, and toluene; esters such as ethyl acetate, n-butyl acetate, decyl acetate, dodecyl acetate, tetradecyl acetate, and hexadecyl acetate; ketones such as acetone and methyl ethyl ketone; ethers such as diethyl ether and dibutyl ether; alcohols such as 1-decanol, 1-dodecanol, 1-tetradecanol, and 1-hexadecanol; nitriles such as acetonitrile and propionitrile; and N,N-dimethyl ether. Examples of suitable solvents include aprotic polar solvents such as acetamide; mineral oils such as kerosene, liquid paraffin, amber oil, and creosote oil; vegetable oils such as castor oil, linseed oil, salad oil, corn oil, soybean oil, sesame oil, rapeseed oil, safflower oil, sunflower oil, palm oil, olive oil, peanut oil, almond oil, grapeseed oil, jojoba oil, rosehip oil, avocado oil, hazelnut oil, and orange oil; animal oils such as fish oil, lanolin oil, squalane, egg yolk oil, cod liver oil, horse oil, and mink oil; and synthetic oils such as ester oil. The amount of the diluent added is preferably 0 to 10,000 parts by mass relative to 100 parts by mass of the total amount of (9E)-9-dodecenal (1), (9Z)-9-dodecenal (2), and (9E)-9,11-dodecadienal (3).

[0030] A propellant is used for sustained release preparations that have a can as a container. The propellant may be one or more of the following: liquefied petroleum gases such as propane, propylene, n-butane, isobutane, and dimethyl ether (hereinafter also referred to as "DME"); halogenated carbon gases such as HFC-152a, HFC-134a, HFO-1234yf, and HFO-1234ze; carbon dioxide; nitrogen gas; and compressed gases such as compressed air. The mass ratio of the total amount of (9E)-9-dodecenal (1), (9Z)-9-dodecenal (2), (9E)-9,11-dodecadienal (3), the additives and the diluent to the propellant is preferably 80:20 to 25:75, and more preferably 45:55 to 65:35, from the viewpoint of pest control effect. The filling amount of the sustained-release preparation having a can as a container is preferably 0.01 mg to 500 g, more preferably 1 mg to 200 g, from the viewpoint of pest control effect. Even an unstable pheromone substance can be stored in a can that can block ultraviolet rays and air, but when an unstable pheromone substance is released little by little, in conventional sustained-release preparations, the pheromone substance released from the nozzle may polymerize and clog the nozzle, causing the sustained-release preparation to no longer function. However, sustained release can be ensured by combining the above three types of compounds (1), (2), and (3). The can of the sustained-release preparation as a container is not particularly limited as long as it is made of a material capable of releasing at least (9E)-9-dodecenal (1), (9Z)-9-dodecenal (2), and (9E)-9,11-dodecadienal (3) in the physiologically active composition for a certain period of time, and examples of the material include metal. The metal used for the can may be any metal that can be used for spraying or dispersing, and examples of the metal include aluminum, stainless steel, and steel.

[0031] The sustained release preparation equipped with a tubular container can store a composition containing at least (9E)-9-dodecenal (1), (9Z)-9-dodecenal (2) and (9E)-9,11-dodecadienal (3), and is suitable because it has a long period of release of (9E)-9-dodecenal (1), (9Z)-9-dodecenal (2) and (9E)-9,11-dodecadienal (3) and the release is uniform. In order to maintain the release at a moderate rate, the inner diameter of the tubular container is preferably 0.01 to 5.0 mm and the wall thickness is preferably 0.05 to 3.0 mm, depending on the material of the tubular container.

[0032] The tubular container of the sustained-release preparation is preferably made of a polymer, since it maintains release at an appropriate rate. As the polymer, a material through which (9E)-9-dodecenal (1), (9Z)-9-dodecenal (2), (9E)-9,11-dodecadienal (3), etc. can permeate and be released to the outside of the polymer membrane at a moderate speed is preferred. Specific examples include natural rubber exemplified by cis-polyisoprene, synthetic rubber exemplified by isoprene rubber, butadiene rubber, and acrylonitrile-butadiene rubber (NBR), polyolefin exemplified by polyethylene and polypropylene, copolymers containing 80% by weight or more of ethylene exemplified by ethylene-vinyl acetate copolymer and ethylene-acrylic acid ester copolymer, biodegradable plastics exemplified by polylactic acid, polycaprolactone, polyhydroxyalkanoate, and cellulose, vinyl acetate and vinyl chloride, polytetrafluoroethylene, etc. From the viewpoints of economy and versatility, synthetic rubber, ethylene-vinyl acetate copolymer, and polylactic acid are preferred. These polymers can also be used as spray containers by increasing the membrane thickness to suppress permeation.

[0033] In the case of reducing the number of release sites without changing the dosage per unit area, it is desirable to change the length of the sustained release preparation having a tubular container without changing the loading amount per unit length of one sustained release preparation having a tubular container. The length is preferably 0.2 to 100 m, more preferably 0.2 to 20 m, and even more preferably 0.3 to 10 m. However, this is not the case when the sustained release preparation having a tubular container is connected in two or more series. In this case, the loading amount per 1 m of one sustained release preparation having a tubular container is preferably 0.005 to 5.5 g.

[0034] The carrier used in the sustained release preparation having a carrier is not particularly limited as long as it can stably hold the physiologically active composition and release at least (9E)-9-dodecenal (1), (9Z)-9-dodecenal (2) and (9E)-9,11-dodecadienal (3) in the physiologically active composition for a certain period of time. Examples of such materials include natural rubber such as cis-polyisoprene, synthetic rubber such as isoprene rubber and butadiene rubber, polyolefins such as polyethylene and polypropylene, sodium metasilicate, silica gel, quartz, polylactic acid, polycaprolactone, polyhydroxyalkanoate, polyglycolic acid, polybutylene succinate, modified polyvinyl alcohol, casein, modified starch, polyhydroxyalkanoic acid such as polyhydroxybutyric acid, polysaccharide derivatives such as cellulose and acetylcellulose, minerals such as zeolite, etc. Furthermore, by processing these materials into a porous structure, it is possible to hold more of the physiologically active composition.

[0035] The container other than the tube or can that the sustained-release preparation is provided with is not particularly limited as long as it is made of a material that can release at least (9E)-9-dodecenal (1), (9Z)-9-dodecenal (2), and (9E)-9,11-dodecadienal (3) in the physiologically active composition for a certain period of time, and examples of the container include caps, laminated bags, capsules, beads, bottles, ampoules, and the like, made of polymeric materials. Examples of polymers for non-tubular polymer containers are the same as those listed for the tubular containers. These polymers can also be used as spray containers by increasing the thickness of the membrane to suppress permeation.

[0036] Next, the method includes at least a step of placing a sustained release formulation including at least a physiologically active composition including at least (9E)-9-dodecenal (1), (9Z)-9-dodecenal (2), and (9E)-9,11-dodecadienal (3) in a field, and releasing at least the (9E)-9-dodecenal (1), (9Z)-9-dodecenal (2), and the (9E)-9,11-dodecadienal (3) in the field. Setothosea asigna This article explains how to control this pest. Setothosea asigna Examples of the control method include mass trapping or attract and kill, push-pull, attract and infect, and mating disruption. According to the present invention, the sustained release formulation is particularly effective in preventing the growth of pests in fields. Setothosea asigna The present invention can be preferably applied to these control methods that target the above-mentioned pests. Setothosea asigna The release of at least (9E)-9-dodecenal (1), (9Z)-9-dodecenal (2) and (9E)-9,11-dodecadienal (3) in the physiologically active composition into the field is not particularly limited as long as it can control the pest, but it is preferable to use the above-mentioned sustained release formulation, for example, actively or passively. Examples of active release (slow release) methods include spraying or scattering from a can, spray bottle, sprinkler, or irrigation equipment as a container or carrier. Examples of passive release (slow release) methods include permeation from a container or carrier.

[0037] The installation of the sustained release formulation in the field is not particularly limited, but in the case of permeation or release from a container or a carrier, or spraying or scattering from a can or a spray bottle, for example, the installation density of the sustained release formulation is preferably 0.10 to 2000 locations / ha, more preferably 0.25 to 1000 locations / ha evenly in the field to be controlled. The amount of release from one release location depends on the field environment and weather conditions, but is not particularly limited as long as it is an amount that can be uniformly drifted in the field, and is preferably 0.001 to 20 g / day. In the case of spraying or scattering from a sprinkler or irrigation equipment, the installation density of the equipment is preferably 0.001 to 50 locations / ha, more preferably 0.003 to 25 locations / ha, uniformly in the field to be controlled. The amount of spraying or scattering from a sprinkler or irrigation equipment per time varies depending on the field environment and weather conditions, but is not particularly limited as long as it is an amount that can be uniformly drifted in the field, and is preferably 0.000001 to 20000 g / location / time, and the frequency of release is preferably 1 to 20 times / day. In this way, the major pests of oil palm in Southeast Asia Setothosea asigna can be prevented. EXAMPLES

[0038] The present invention will be described in more detail below with reference to examples, but the present invention is not limited to the following examples. Example 1, Reference Example 1 (9E)-9-dodecenal (1), (9Z)-9-dodecenal (2) and (9E)-9,11-dodecadienal (3) are mixed in a mass ratio of 100:1:10, and 10.00 mg of the mixture (Example 1) or 10.00 mg of the mixture (Reference Example 1) is mixed in a mass ratio of 100:1:100, and sealed in a polyethylene tube with an inner diameter of 0.84 mm, a thickness of 0.55 mm and a length of 2 cm, to produce a sustained release formulation. The sustained release formulation obtained is placed in a thermostatic chamber with an air velocity of 0.3 m / s and a temperature of 30°C, and the mixture inside the formulation is released. Three sustained-release preparations were collected on days 0, 14, 21, and 28, and the remaining amounts of (9E)-9-dodecenal (1), (9Z)-9-dodecenal (2), and (9E)-9,11-dodecadienal (3) were quantified by internal standard method / gas chromatogram analysis. Furthermore, the average value of the three remaining rates of (9E)-9-dodecenal (1), (9Z)-9-dodecenal (2), and (9E)-9,11-dodecadienal (3) was calculated. The results are shown in Figures 1 to 3.

[0039] As a result of testing in a constant temperature bath, in Example 1 in which (9E)-9-dodecenal (1), (9Z)-9-dodecenal (2), and (9E)-9,11-dodecadienal (3) were encapsulated in a mass ratio of 100:1:10, the components continued to be released from the formulation for approximately one month, whereas in Reference Example 1 in which (9E)-9-dodecenal (1), (9Z)-9-dodecenal (2), and (9E)-9,11-dodecadienal (3) were encapsulated in a mass ratio of 100:1:100, all three components had not been released after approximately 20 days had elapsed. As mentioned above, this was thought to be because a large amount of the less stable (9E)-9,11-dodecadienal was used in Reference Example 1, which polymerized to form a film on the surface of the formulation, preventing the release of the pheromone compound in the formulation. This result demonstrated that it is difficult to continue releasing the pheromone component for a long period of time in a formulation with a high ratio of (9E)-9,11-dodecadienal (3).

[0040] Example 2, Reference Example 2 A mixed solution of 7.08 mg (Example 2) in which (9E)-9-dodecenal (1), (9Z)-9-dodecenal (2), and (9E)-9,11-dodecadienal (3) were mixed in a mass ratio of 100:1:10, or a mixed solution of 7.05 mg (Reference Example 2) in which they were mixed in a mass ratio of 100:1:100 was prepared. 2.08 parts by mass of BHT (2,6-di-tert-butyl-4-methylphenol) and 2.08 parts by mass of HBMCBT (2-(2'-hydroxy-3'-tert-butyl-5'-methylphenyl)-5-chlorobenzotriazole) were added as additives to 100 parts by mass of the mixed solution, Setothosea asigna The composition was packed into a polyethylene tube having an inner diameter of 0.84 mm, a membrane thickness of 0.55 mm, and a length of 20 cm to prepare a sustained-release preparation. A white sticky trap was used to evaluate the attraction of the sustained-release formulation. As shown in FIG. 4, the white sticky trap consists of a triangular roof and a bottom plate, and the entrance for insects is narrow. Then, a sticky substance is attached to the upper surface of the bottom plate, and an attractant is placed inside the trap for use. In other words, the trap is designed to capture only insects that approach the sustained-release formulation, and to prevent non-target insects from jumping in as much as possible. Usually, the attractant is placed directly on the sticky surface, but in Example 2 and Reference Example 2, the attractant was fixed to the trap by inserting both straight parts (non-curved parts) of a tube bent into a U-shape into the slits in the ridge of the triangular roof so that the release from the tube surface would not be hindered by the sticky substance. A in FIG. 4 shows a tubular sustained-release formulation bent into a U-shape. During the period from October 23 to November 6, 2019, one trap containing the sustained release formulation manufactured in Example 2 or one trap containing the sustained release formulation manufactured in Reference Example 2 was Setothosea asigna The traps were set up within a 4.5 ha area (total of 9 ha for Example 2 and Reference Example 2) in an oil palm plantation in Indonesia where the insects live. The number of adult males trapped and killed in each trap was counted by collecting the sticky boards every 7 days and replacing them with new ones. The number of adult males caught in one trap (over 7 days) was used as the number of luring insects, and the attractant effect was evaluated. The results are shown in Table 1.

[0041] [Table 1]

[0042] In Example 2, the (9Z)-9-dodecenal (2) was added for 14 days. Setothosea asigna In the case of the compound containing (9Z)-9-dodecenal (2), the number of lures was greater in Example 2, in which the ratio of (9E)-9,11-dodecadienal (3) to (9E)-9-dodecenal (1) was smaller, than in Reference Example 2, in which equal amounts of (9E)-9-dodecenal (1) and (9E)-9,11-dodecadienal (3) were contained. From these results, it can be seen that by adding a certain ratio of (9Z)-9-dodecenal (2), which was thought to be an inactive ingredient, even when the ratio of (9E)-9,11-dodecadienal (3) to (9E)-9-dodecenal (1) was small, Setothosea asigna It is believed that this may enable the attraction of the species to be maintained.

[0043] Example 3 (9E)-9-dodecenal (1), (9Z)-9-dodecenal (2), and (9E)-9,11-dodecadienal (3) were mixed in a mass ratio of 100:1:70 to prepare 60.0 mg of a mixed liquid. 2.08 parts by mass of BHT (2,6-di-tert-butyl-4-methylphenol) and 2.08 parts by mass of HBMCBT (2-(2'-hydroxy-3'-tert-butyl-5'-methylphenyl-5-chlorobenzotriazole)) were added as additives to 100 parts by mass of the mixed liquid. Setothosea asigna The composition was packed into a polyethylene tube having an inner diameter of 0.84 mm, a thickness of 0.55 mm, and a length of 17 cm to prepare a sustained release formulation. To evaluate the attractiveness of the sustained-release formulation, a white sticky trap as shown in Figure 4 was used, as in Example 2, and the tube was bent into a U-shape and both straight parts (non-curved parts) of the tube of the sustained-release formulation bent into a U-shape were inserted into the slits in the ridge of the triangular roof to secure it to the trap. Between February 23 and March 23, 2023, traps containing sustained-release preparations will be Setothosea asigna One trap was installed within an area of ​​0.4 ha in an oil palm plantation where the insects live. The number of adult males killed by the trap was counted by collecting the sticky boards every seven days and replacing them with new ones. The number of adult males caught in one trap (over seven days) was used as the number of luring insects, and the attractant effect was evaluated. The results are shown in Table 2.

[0044] Example 4 The amount of the mixture was changed to 46.0 mg, which was a mixture of (9E)-9-dodecenal (1), (9Z)-9-dodecenal (2) and (9E)-9,11-dodecadienal (3) in a mass ratio of 100:1:30, and the tube length was changed to 13 cm to make the amount of (9E)-9-dodecenal (1) released per day consistent with that of Example 3. The manufacturing and evaluation of the attractant effect were carried out in the same manner as in Example 3. The results are shown in Table 2.

[0045] Example 5 The amount of the mixture was changed to 39.0 mg, which was a mixture of (9E)-9-dodecenal (1), (9Z)-9-dodecenal (2) and (9E)-9,11-dodecadienal (3) mixed at a mass ratio of 100:1:10, and the tube length was changed to 11 cm to make the amount of (9E)-9-dodecenal (1) released per day consistent with that of Example 3. The manufacturing and evaluation of the attractant effect were carried out in the same manner as in Example 3. The results are shown in Table 2.

[0046] Example 6 The amount of the mixture was changed to 37.3 mg, which was a mixture of (9E)-9-dodecenal (1), (9Z)-9-dodecenal (2) and (9E)-9,11-dodecadienal (3) mixed at a mass ratio of 100:1:5, and the tube length was changed to 10.5 cm to make the amount of (9E)-9-dodecenal (1) released per day consistent with that of Example 3. The manufacturing and evaluation of the attractant effect were carried out in the same manner as in Example 3. The results are shown in Table 2.

[0047] Example 7 The amount of the mixture was changed to 48.2 mg, which was a mixture of (9E)-9-dodecenal (1), (9Z)-9-dodecenal (2) and (9E)-9,11-dodecadienal (3) mixed in a mass ratio of 100:28:10, and the tube length was changed to 11 cm to make the amount of (9E)-9-dodecenal (1) released per day consistent with that of Example 3. The manufacturing and evaluation of the attractant effect were carried out in the same manner as in Example 3. The results are shown in Table 2.

[0048] [Table 2]

[0049] In all the tests of Examples 3 to 7, the amount of (9E)-9-dodecenal (1) encapsulated was the same, 35.0 mg. The results of Examples 3 to 6 showed that by containing a predetermined amount of (9Z)-9-dodecenal (2), even if the amount of (9E)-9,11-dodecadienal (3) was 5 to 70 parts by mass relative to 100 parts by mass of (9E)-9-dodecenal (1), there was sufficient attractant force. In addition, the results of Examples 5 and 7 showed that the attractant force could be increased by adding more (9Z)-9-dodecenal (2). Thus, unlike the results of Non-Patent Document 2, the attractant force could be increased by adding a predetermined amount of (9Z)-9-dodecenal (2), and an agent that maintains a certain level of attractant force was successfully obtained even if the content ratio of (9E)-9,11-dodecadienal (3) to (9E)-9-dodecenal (1) was low. Furthermore, by including a specific amount of (9Z)-9-dodecenal (2), it was possible to reduce the ratio of (9E)-9,11-dodecadienal (3) to (9E)-9-dodecenal (1), resulting in successful long-term attraction of the compound for at least four weeks. Furthermore, the experiment was continued for an additional four weeks (total of eight weeks) for Example 4 alone, and as a result, nine adult males were still captured even in the eighth week, confirming that attraction could be continued for two months. [Explanation of symbols]

[0050] A. Sustained release preparations

Claims

1. 100 parts by weight of (9E)-9-dodecenal, 1 to 40 parts by weight of (9Z)-9-dodecenal, and 1 to 70 parts by mass of (9E)-9,11-dodecadienal A composition comprising at least

2. A composition comprising at least 100 parts by mass of (9E)-9-dodecenal, 1 to 40 parts by mass of (9Z)-9-dodecenal, and 1 to 70 parts by mass of (9E)-9,11-dodecadienal; a carrier or container for supporting or storing the composition and releasing at least the (9E)-9-dodecenal, the (9Z)-9-dodecenal, and the (9E)-9,11-dodecadienal; A sustained release formulation for controlling Setothosea asigna comprising at least

3. A method for controlling Setothosea asigna, comprising at least a step of placing the sustained release formulation according to claim 2 in a field and releasing at least the (9E)-9-dodecenal, the (9Z)-9-dodecenal and the (9E)-9,11-dodecadienal into the field.

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