Polycyclic compound, method for producing same, and use thereof

Abstract

A polycyclic compound represented by formula (A) is a novel polycyclic compound that exhibits hatch-inducing activity against cyst nematodes. [In the formula, R1 represents a carboxy group or CH2CH=C(CH3)2.]

Description

Polycyclic compounds, methods for producing the same, and uses thereof

[0001] This invention relates to novel polycyclic compounds, methods for producing the same, and uses thereof.

[0002] Cyst nematodes, which parasitize plants, are pests that stunt plant growth and cause significant yield reductions by infesting crops and depriving them of nutrients. Because cyst nematode eggs are protected by a hard shell called a cyst, it is generally known that controlling cyst nematodes is difficult.

[0003] Cyst nematodes hatch in response to specific chemical substances (hatching inducers) secreted from plant roots, and then parasitize the roots, causing damage. Therefore, a method of control has been proposed in which hatching inducers are applied to the field before planting to induce hatching of cyst nematodes, which then starve to death. Solanoelclepin A is known as a hatching inducer derived from natural products. However, the amount of solanoeclepin A that can be obtained from isolation from natural products or through organic synthesis is extremely small, making practical application difficult.

[0004] Furthermore, Patent Document 1 discloses a control agent for potato cyst nematodes.

[0005] Japanese Patent Publication No. 2022-128804

[0006] However, the active ingredient compound in the pest control agent described in Patent Document 1 is not derived from a natural product, and the number of naturally derived compounds that exhibit hatching-inducing activity against cyst nematodes is limited to a few types, including solanoeclepin A. In addition, from the viewpoint of elucidating the biosynthesis of solanoeclepin A, the development of novel hatching-inducing substances was required. The object of the present invention is to provide a novel polycyclic compound that exhibits hatching-inducing activity against cyst nematodes.

[0007] The present invention is as follows: [1] Formula (A) [In the formula, R １ is a carboxyl group or CH ２ CH = C(CH ３ ) ２This represents a polycyclic compound represented by ] (hereinafter also referred to as compound (A)). [2] Formula (I) The polycyclic compound described in [1], represented by [3] (also referred to as compound (I)). [3] Formula (II) The polycyclic compound described in [1], represented by [4] (also referred to as compound (II)). The compound represented by formula (M2) (hereinafter also referred to as compound (M1)) A step of converting the compound represented by formula (M2) (hereinafter also referred to as compound (M2)) to a compound represented by formula (M4) A step of converting the compound represented by formula (M4) (hereinafter also referred to as compound (M4)) to formula (M5) A step of converting the compound represented by formula (M5) (hereinafter also referred to as compound (M5)) to a compound represented by formula (M6) A method for producing a polycyclic compound according to [2], comprising the steps of: converting to a compound represented by formula (M6) (hereinafter also referred to as compound (M6)); and converting the compound represented by formula (M6) to a polycyclic compound represented by formula (I). [5] Formula (M1) The compound represented by formula (M2) A step of converting the compound represented by formula (M2) to a compound represented by formula (M4) A step of converting the compound represented by formula (M4) to a compound represented by formula (M7) A step of converting the compound represented by formula (M7) (hereinafter also referred to as compound (M7)) to formula (M8) A step of converting the compound represented by formula (M8) (hereinafter also referred to as compound (M8)) to formula (M10) A method for producing a polycyclic compound according to [3], comprising the steps of: converting to a compound represented by formula (M10) (hereinafter also referred to as compound (M10)); and converting the compound represented by formula (M10) to a polycyclic compound represented by formula (II). [6] A cyst nematode control agent containing the polycyclic compound according to [1]. [7] A method for controlling cyst nematodes, comprising applying an effective amount of the polycyclic compound according to [1] or the cyst nematode control agent according to [6] to a habitat of cyst nematodes.

[0008] According to the present invention, it is possible to provide a novel polycyclic compound that exhibits hatching-inducing activity against cyst nematodes.

[0009] Figure 1 shows the test results for Test Example 1. Figure 2 shows the test results for Test Example 1. Figure 3 shows the test results for Test Example 1. Figure 4 shows the test results for Test Example 1.

[0010] The polycyclic compound of the present invention is of formula (A) [In the formula, R １ is a carboxyl group or CH ２ CH = C(CH ３ ) ２ It represents a polycyclic compound represented by [ ].

[0011] The polycyclic compounds of the present invention include the following embodiments.

[0012] [Embodiment 1] A polycyclic compound represented by formula (I). [Embodiment 2] A polycyclic compound represented by formula (II).

[0013] Examples of methods for producing compound (I) and compound (II) are described below.

[0014] Compound (I) according to Embodiment 1 can be produced by a manufacturing method that includes the steps of converting compound (M1) to compound (M2), converting compound (M2) to compound (M4), converting compound (M4) to compound (M5), converting compound (M5) to compound (M6), and converting compound (M6) to compound (I).

[0015] The starting material compound (M1) is a known compound called cycloartenol and can be produced, for example, by solvolysis of γ-oryzanol. For example, compound (M1) can be produced by dissolving γ-oryzanol in an organic solvent, adding potassium hydroxide, and stirring under heating and reflux. During the synthesis of compound (M1), 24-methylenecycloartanol may be simultaneously produced.

[0016] [Step of converting compound (M1) to compound (M2)] An example of the step of converting compound (M1) to compound (M2) is as follows. Compound (M1) is dissolved in an organic solvent, and a benzoylation reagent such as benzoyl chloride (BzCl) is reacted in the presence of a base such as pyridine to obtain a benzoylated product. The obtained benzoylated product is dissolved in an organic solvent, reacted with m-chloroperbenzoic acid (mCPBA), and then a first mixture is obtained by appropriate post-treatment operations. The obtained first mixture is dissolved in an organic solvent, reacted with ortho-periodic acid (H ５ IO ６ ), and then a second mixture is obtained by appropriate post-treatment operations. The obtained second mixture is dissolved in an organic solvent, and purified water, 2-methyl-2-butene, sodium dihydrogen phosphate monohydrate (NaH ２ PO ４ ·H ２ O) and sodium chlorite (NaClO ２ ) are added and reacted to produce compound (M2). During the synthesis of compound (M2), the compound represented by formula (M3) (hereinafter also referred to as compound (M3)) may be simultaneously produced.

[0017] [Step of converting compound (M2) to compound (M4)] An example of the step of converting compound (M2) to compound (M4) is as follows. Compound (M2) is dissolved in an organic solvent such as dichloromethane, and reacted with trifluoroacetic anhydride (TFAA) in the presence of a base such as pyridine to produce compound (M4).

[0018] [Step of converting compound (M4) to compound (M5)] An example of the process for converting compound (M4) to compound (M5) is as follows: Dissolve compound (M4) in an organic solvent, and sodium bicarbonate (NaHCO3) ３ The crude product is obtained by sequentially adding ), oxone and reacting. The obtained crude product is dissolved in an organic solvent and triethylamine (Et ３ By reacting tert-butyldimethylsilyl chloride (TBSCl) in the presence of a base such as N), an intermediate compound represented by formula (S1) (hereinafter also referred to as compound (S1)) is obtained. Compound (M5) can be produced by reacting compound (S1) with m-chloroperbenzoic acid (mCPBA).

[0019] [Process for converting compound (M5) to compound (M6)] An example of the process for converting compound (M5) to compound (M6) is as follows: Compound (M5) is dissolved in an organic solvent, hydrolyzed with saturated potassium hydroxide aqueous solution, etc., and after the reaction is complete, a crude product is obtained by purification. The obtained crude product is dissolved in an organic solvent and trimethylsilyldiazomethane (TMSCHN) is obtained. ２ By esterification using ) etc., an intermediate compound represented by formula (S2) (hereinafter also referred to as compound (S2)) is obtained. Compound (S2) is dissolved in an organic solvent and a boron trifluoride diethyl ether complex (BF ３ ・OET ２ Compound (M6) can be produced by reacting it with Lewis acids such as ).

[0020] [Process for converting compound (M6) to compound (I)] An example of the process for converting compound (M6) to compound (I) is as follows: Compound (I) of the present invention can be produced by dissolving compound (M6) in an organic solvent and hydrolyzing it using potassium hydroxide or the like.

[0021] Compound (II) according to Embodiment 2 can be produced by a manufacturing method that includes the steps of converting compound (M1) to compound (M2), converting compound (M2) to compound (M4), converting compound (M4) to compound (M7), converting compound (M7) to compound (M8), converting compound (M8) to compound (M10), and converting compound (M10) to compound (II).

[0022] The above explanation applies to the method for producing the starting material compound (M1), the process of converting compound (M1) to compound (M2), and the process of converting compound (M2) to compound (M4).

[0023] [Process for converting compound (M4) to compound (M7)] An example of the process for converting compound (M4) to compound (M7) is as follows: Compound (M4) is dissolved in an organic solvent, and sodium bicarbonate and oxone are added in sequence and reacted to obtain a first crude product. The obtained first crude product is dissolved in an organic solvent and reacted with a saturated potassium hydroxide aqueous solution, and then purified to obtain a second crude product. The obtained second crude product is dissolved in an organic solvent and reacted with potassium carbonate and methyl iodide (MeI) to produce compound (M7).

[0024] [Process for converting compound (M7) to compound (M8)] An example of the process for converting compound (M7) to compound (M8) is as follows: Compound (M8) can be produced by dissolving compound (M7) in an organic solvent and reacting it with a Lewis acid such as a boron trifluoride diethyl ether complex. During the synthesis of compound (M8), a compound represented by formula (M9) (hereinafter also referred to as compound (M9)) may be produced simultaneously.

[0025] Alternatively, compound (M8) can also be produced by the following method. Compound (M8) can be produced by dissolving compound (M7) in 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP) and heating it at a temperature of approximately 70°C. Compound (M9) may also be produced simultaneously during the synthesis of compound (M8).

[0026] [Process for converting compound (M8) to compound (M10)] An example of the process for converting compound (M8) to compound (M10) is as follows: Compound (M8) is dissolved in an organic solvent and reacted with aluminum diisobutylhydride (DIBAL) to obtain an intermediate compound represented by formula (S3) (hereinafter also referred to as compound (S3)). Compound (M10) can be produced by dissolving compound (S3) in an organic solvent and performing Swern oxidation (Swern Ox.).

[0027] [Process for converting compound (M10) to compound (II)] An example of the process for converting compound (M10) to compound (II) is as follows: Dissolve compound (M10) in an organic solvent and dissolve isopropylidenetriphenylphosphoran ((CH ３ ) ２ C = PPh ３ Compound (II) can be produced by reacting it with ).

[0028] The reaction conditions in the methods for producing compound (I) and compound (II) described above, such as reagents, solvents, reaction temperature, reaction time, and purification treatment, are not limited to the above-described reaction conditions and can be appropriately selected as needed. The reaction is usually carried out in a solvent. Examples of solvents used in the reaction include alcohols, ketones, ethers, amides, esters, nitriles, halogenated hydrocarbons, aromatic hydrocarbons, aliphatic hydrocarbons, aprotic polar solvents, nitrogen-containing aromatic compounds, and mixtures of two or more of these. The reaction temperature is usually in the range of -50°C to 100°C. The reaction time is usually in the range of 1 to 24 hours, and may be 1 to 5 days if necessary. After the reaction is complete, post-treatment operations such as extraction, washing, drying, and concentration can be performed. For example, water can be added to the reactants, extracted with an organic solvent, the organic layer can be washed with purified water, saturated brine, etc., as needed, and then the organic layer can be dried and concentrated. The obtained compounds can be further purified by chromatography, recrystallization, etc.

[0029] The cyst nematode control agent of the present invention contains compound (A). Furthermore, the method for controlling cyst nematodes of the present invention involves applying an effective amount of compound (A) or a cyst nematode control agent containing compound (A) to a habitat of cyst nematodes. Another embodiment of the present invention includes the following.

[0030] [Embodiment 3] A cyst nematode control agent comprising compound (I) or compound (II). [Embodiment 4] A method for controlling cyst nematodes, comprising applying an effective amount of compound (I) or compound (II), or the cyst nematode control agent according to Embodiment 3, to a habitat of cyst nematodes.

[0031] The polycyclic compound of the present invention (compound (I) or compound (II)) exhibits hatching-inducing activity against cyst nematodes. Therefore, the polycyclic compound of the present invention can be suitably used as a control agent for cyst nematodes. Examples of cyst nematodes include soybean cyst nematodes (Heterodera glycines), clover cyst nematodes (Heterodera trifolii), wheat cyst nematodes (Heterodera avenae), rice cyst nematodes (Heterodera elachista), hop cyst nematodes (Heterodera humuli), potato cyst nematodes (Globodera rostochiensis), white potato cyst nematodes (Globodera pallida), tobacco cyst nematodes (Globodera tabacum), mugwort cyst nematodes (Globodera hypolysi), cactus cyst nematodes (Cactodera cacti), and bamboo cyst nematodes (Afenestrata koreana).

[0032] The cyst nematode control agent according to Embodiment 3 contains compound (I) or compound (II) as an active ingredient. The cyst nematode control agent may contain both compound (I) and compound (II) as active ingredients. The cyst nematode control agent can also be formulated into aqueous suspensions, oily suspensions, oils, emulsions, microemulsions, microcapsules, wettable powders, wettable granules, powders, granules, tablets, aerosols, resin formulations, etc. The cyst nematode control agent may consist only of the active ingredient.

[0033] The method for controlling cyst nematodes according to Embodiment 4 involves applying an effective amount of compound (I) or compound (II), or the cyst nematode control agent according to Embodiment 3, to the habitat of the cyst nematodes (plants, soil, etc.). Examples of the methods for controlling cyst nematodes according to Embodiment 4 include foliar treatment, soil treatment, root treatment, shower treatment, fumigation treatment, water surface treatment, and seed treatment.

[0034] When applying the polycyclic compound or cyst nematode control agent of the present invention to soil, it is preferable to apply it to the soil inhabited by cyst nematodes before cultivating plants. This allows the cyst nematodes in the soil to be cultivated to hatch and starve to death before the plants are grown. In other words, the cyst nematode control method according to Embodiment 4 may also be a cyst nematode control method in which an effective amount of the polycyclic compound or cyst nematode control agent of the present invention is applied to the soil to be cultivated before the plants are grown.

[0035] When applying the polycyclic compound or cyst nematode control agent of the present invention to soil, the application rate is 10,000 m ２ The amount of the polycyclic compound of the present invention per unit is usually 1 to 10,000 g. When the polycyclic compound or cyst nematode control agent of the present invention is formulated as an emulsion, wettable powder, flowable formulation, etc., it is usually diluted with water to an active ingredient concentration of 0.01 to 10,000 ppm by mass before application, while granular formulations, powders, etc., are usually applied as is.

[0036] The present invention will be described in more detail below with reference to manufacturing examples, etc., but the present invention is not limited to these examples.

[0037] Preparation Example: Compounds (I) and (II) were prepared according to the following reaction scheme. Each step of the reaction scheme is shown in detail in Synthesis Examples 1 to 11.

[0038] Synthesis Example 1: Synthesis of Compound (M1) γ-oryzanol (101 g) was mixed with ethanol (800 mL) and potassium hydroxide (100 g) and stirred under reflux for 6 hours. After the reaction mixture cooled to room temperature, it was poured into water (1.00 L), extracted with ethyl acetate (1.00 L), and washed with saturated brine (1.00 L). The aqueous layer was extracted with ethyl acetate (800 mL x 2), washed with saturated brine, and the organic layers were combined and dried over sodium sulfate, and the solvent was removed under reduced pressure. The resulting crude product was purified by silica gel chromatography (hexane-ethyl acetate = 100:0 to 4:1), and the fraction containing cycloartenol (compound (M1)) was concentrated to obtain a grayish-white solid (47.0 g).

[0039] Synthesis Example 2: Synthesis of Compound (M2) Assuming that all of the mixture obtained in Synthesis Example 1 is compound (M1), the following experiment was carried out. To a solution of the mixture containing compound (M1) (20.0 g, 0.0459 mol) in dichloromethane (120 mL), pyridine (22.2 mL, 0.276 mol) and benzoyl chloride (10.8 mL, 0.0937 mol) were added and the mixture was reacted at room temperature for 19 hours, after which 3N hydrochloric acid (120 mL) was added to stop the reaction. After separating the organic layer, the aqueous layer was extracted with dichloromethane (100 mL x 2 times), dried over sodium sulfate, and the solvent was removed under reduced pressure. The resulting crude product was recrystallized from ethanol to obtain the benzoyl compound (23.9 g) as colorless needle-shaped crystals. This was dissolved in dichloromethane (442 mL), 70% m-chloroperbenzoic acid (10.9 g, 0.0442 mol) was added, and the mixture was stirred at room temperature for 1 hour. To the reaction mixture, 45 mL of 1.0 M sodium thiosulfate aqueous solution and 400 mL of saturated sodium bicarbonate aqueous solution were added and stirred for a while. After separating the organic layer, the aqueous layer was extracted with dichloromethane (100 mL x 2), the combined organic layers were dried over sodium sulfate, and the solvent was removed under reduced pressure. The resulting mixture was dissolved in 874 mL of diethyl ether, 15.0 g, 0.0658 mol of orthoperiodic acid was added, and the mixture was stirred at room temperature for 2 hours. After adding 200 mL of purified water to the reaction mixture and separating the organic layer, the aqueous layer was extracted with diethyl ether (200 mL), the combined organic layers were washed with saturated brine, dried over sodium sulfate, and the solvent was removed under reduced pressure. The resulting mixture was dissolved in 700 mL of t-butyl alcohol, and purified water (140 mL), 30.9 mL, 0.292 mol of 2-methyl-2-butene, 4.02 g, 0.0292 mol of sodium dihydrogen phosphate monohydrate, and 2.64 g, 0.0292 mol of sodium chlorite were added. The mixture was stirred at room temperature for 1.5 hours. Purified water (400 mL) was added to the reaction mixture, and then it was extracted with ethyl acetate (400 mL x 2). After washing with saturated brine and drying over sodium sulfate, the solvent was removed under reduced pressure. The resulting crude product was purified by silica gel flash chromatography (hexane-ethyl acetate = 20:1 to 5:1, hexane-ethyl acetate containing 5% ethanol = 5:1) to obtain compound (M2) (5.65 g) as a grayish-white solid.For compound (M3), a ketone compound, a pure sample was obtained for spectral analysis by repurifying a small amount of the sample. [Compound (M2)] １ H-NMR (CDCl ３ ) δ: 0.39 (d, J=4.1Hz, 1H), 0.62 (d, J=4.1Hz, 1H), 0.82 (td, J=12.5, 2.4Hz, 1H), 0.89 (d, J=6.5Hz, 3H), 0.91 (s, 3H), 0.92 ( s, 3H), 0.98 (s, 3H), 1.05 (s, 3H), 1.06-1.19 (m, 2H), 1.27-1.39 (m, 6H), 1.44 (m, 1H), 1.48 (dd, J = 12.3, 4.1Hz, 1H), 1.53 ( dd. H), 2.43 (ddd, J=15.7, 10.2, 5.2Hz, 1H), 4.82 (dd, J=11.3, 4.5Hz, 1H), 7.44 (m, 2H, Bz), 7.56 (m, 1H, Bz), 8.06 (m, 2H, Bz). １３ C-NMR (CDCl ３ ) δ: 15.6, 18.0, 18.2, 19.4, 20.3, 21.1, 25.7, 26.0, 26.1, 26.6, 27.0, 28.1, 30.0, 31.1, 31.3, 31.8, 3 3.0, 35.6, 35.8, 40.0, 45.5, 47.4, 48.0, 49.0, 52.2, 81.4, 128.5, 129.7, 131.1, 132.9, 166.4, 180.1. HRMS-ESI (m / z): found, 519.3466 [MH] － ;calcd. for C ３４ H ４７ O ４ , 519.3480. [Compound (M3)] １ H-NMR (CDCl ３) δ: 0.37 (d, J=4.1Hz, 1H), 0.61 (d, J=4.1Hz, 1H), 0.83 (td, J= 12.5, 2.4Hz, 1H), 0.86 (d, J=6.5Hz, 3H), 0.90 (s, 3H), 0.91 (s, 3H), 0.96 (s, 3H), 1.04 (s, 3H), 1.09 (d, J=7.0Hz, 6H), 1.06-1 .18 (m, 2H), 1.19-1.43 (m, 7H), 1.47 (dd, J=12.3, 4.3Hz, 1H), 1 . 52 (dd, J=12.5, 4.8Hz, 1H), 1.55-1.85 (m, 8H), 1.87-2.06 (m, 3H), 2.37 (ddd, J=16.6, 9.8, 6.0Hz, 1H), 2.49 (ddd, J=16.6, 1 0.2, 5.1Hz, 1H), 2.61 (sept, J=7.0Hz, 1H), 4.81 (dd, J=11.3, 4.5Hz, 1H), 7.43 (m, 2H, Bz), 7.54 (m, 1H, Bz), 8.05 (m, 2H, Bz). １３ C-NMR (CDCl ３ ) δ: 15.6, 18.16, 18.20, 18.4, 18.5, 19.4, 20.2, 21.0, 2 5.7, 25.9, 26.1, 26.6, 27.0, 28.2, 29.9, 30.2, 31.7, 32. 9, 35.6, 35.8, 37.6, 39.9, 40.9, 45.4, 47.3, 48.0, 48.9 , 52.3, 81.4, 128.4, 129.6, 131.0, 132.8, 166.4, 215.7. HRMS-ESI (m / z): [M+H] ＋ calcd for C ３７ H ５５ O ３ , 547.4119; found, 547.4146.

[0040] Synthesis Example 3: Synthesis of Compound (M4) To a solution of compound (M2) (0.99 g, 1.9 mmol) in dichloromethane (19 mL), pyridine (0.96 mL, 12 mmol) and anhydrous trifluoroacetic acid (0.96 mL, 6.9 mmol) were added dropwise at 0°C, and the mixture was stirred while slowly increasing the temperature to room temperature. After reacting at room temperature for 24 hours, 90% aqueous acetonitrile (19 mL) was added at 0°C and the mixture was stirred for 10 minutes, then the temperature was increased to room temperature and stirred for a further 30 minutes. Purified water (19 mL) was added, and the mixture was extracted with dichloromethane (10 mL x 2). After drying over sodium sulfate, the solvent was removed under reduced pressure. The resulting crude product was purified by silica gel flash chromatography (hexane-ethyl acetate = 20:1 to 10:1) to obtain compound (M4) (0.88 g, 80%) as a pale yellow solid. [Compound (M4)] １ H-NMR (CDCl ３ ) δ: 0.39 (d, J=4.1Hz, 1H), 0.62 (d, J=4.1Hz, 1H), 0.82 (td, J=12.6, 2.4Hz, 1H), 0.89 (d, J=6.5Hz, 3H), 0.92 (s, 3H), 0. 92 (s, 3H), 0.97 (s, 3H), 1.05 (s, 3H), 1.07-1.19 (m, 2H), 1.27-1.41 (m, 6H), 1.44 (m, 1H), 1.48 (dd, J = 12.5, 4.5Hz, 1H) , 1.53 (dd, J = 12.4, 4.8 Hz, 1H), 1.56-1.80 (m, 6H), 1.83-1.98 (m, 3H), 2.03 (m, 1H), 2.66 (ddd, J = 18.4, 9.2, 5.9Hz, 1H) , 2.77 (ddd, J=18.4, 9.9, 5.1Hz, 1H), 4.82 (dd, J=11.3, 4.5Hz, 1H), 7.44 (m, 2H, Bz), 7.55 (m, 1H, Bz), 8.06 (m, 2H, Bz). １３ C-NMR (CDCl ３ ) δ: 15.6, 18.1, 18.2, 19.4, 20.2, 21.1, 25.7, 26.0, 26.1, 26.5, 27.0, 28.1, 28.8, 30.0, 31 .8, 33.0, 33.8, 35.5, 35.6, 40.0, 45.5, 47.3, 48.0, 49.0, 52.2, 81.4, 115.8 (q, J=292Hz, CF ３), 128.5, 129.7, 131.1, 132.9, 166.4, 192.2 (q, J = 34.5Hz, COCF ３ ). HRMS-ESI (m / z): [MH] － calcd for C ３５ H ４６ F ３ O ３ , 571.3405; found, 571.3400.

[0041] Synthesis Example 4: Synthesis of Compound (M7) To a solution of compound (M4) (0.57 g, 1.0 mmol) in tert-butyl alcohol (150 mL), 100 mL of 0.10 mM ethylenediaminetetraacetic acid disodium aqueous solution, 2.5 g, 30 mmol of sodium bicarbonate, and oxone (6.2 g, 10 mmol) were added in sequence, and the mixture was vigorously stirred at room temperature for 4 hours. The solution was diluted with purified water (200 mL), extracted with dichloromethane (100 mL x 3), dried over sodium sulfate, and the solvent was removed under reduced pressure. The resulting crude product was dissolved in ethanol (50 mL), and saturated potassium hydroxide aqueous solution (25 mL) was added dropwise while cooling to 0°C, followed by stirring at room temperature for 11 hours. 50% acetic acid aqueous solution (50 mL) was added dropwise over 20 minutes, followed by extraction with ethyl acetate (50 mL x 3). The resulting organic layer was washed with saturated brine, dried over sodium sulfate, and the solvent was removed under reduced pressure. The crude product obtained was dissolved in N,N-dimethylformamide (100 mL), potassium carbonate (2.8 g, 20 mmol) and methyl iodide (0.65 mL, 10 mmol) were added, and the mixture was stirred at room temperature for 8 hours. After dilution with purified water (400 mL), the mixture was extracted with diethyl ether (100 mL x 3), the organic layer was washed with saturated brine, dried over sodium sulfate, and the solvent was removed under reduced pressure. The crude product obtained was purified by silica gel flash chromatography (hexane-ethyl acetate = 5:1 to 4:1) to obtain compound (M7) (0.30 g, three-step yield 66%) as a pale yellow solid. [Compound (M7)] １ H-NMR (CDCl ３) δ: 0.38 (d, J=4.2Hz, 1H), 0.55 (d, J=4.2Hz, 1H), 0.77 (td, J=12.6, 2.4Hz, 1H), 0.81 (s, 3H ), 0.87 (d, J = 6.5 Hz, 3H), 0.97 (s, 3H), 1.09 ( s, 3H), 1.10-1.17 (m, 2H), 1.21 (s, 3H), 1.22- 1.34 (m, 4H), 1.34-1.56 (m, 8H), 1.58-1.68 ( m, 2H), 1.76 (m, 1H), 1.87-2.13 (m, 5H), 2.25 ( ddd, J=15.7, 8.6, 7.6Hz, 1H), 2.42 (dd, J=15. 7, 9.0, 5.3Hz, 1H), 3.29 (m, 1H), 3.67 (s, 3H). １３ C-NMR (CDCl ３ ) δ: 13.8, 14.2, 20.1, 21.17, 21.22, 21.7, 25.6, 26.1, 26.4, 26.6, 26.9, 27.9, 30.3, 30. 5, 32.1, 32.5, 36.2, 39.3, 40.6, 41.0, 47.4 , 49.1, 49.6, 51.1, 51.7, 78.9, 86.5, 174.6. HRMS-ESI (m / z): [M+H] ＋ calcd for C ２８ H ４７ O ４ , 447.3469; found, 447.3469.

[0042] Synthesis Example 5: Synthesis of Compound (M8) To a solution of compound (M7) (0.26 g, 0.59 mmol) in dichloromethane (12 mL), boron trifluoride diethyl ether complex (0.60 mL, 4.8 mmol) was added dropwise at -40°C, and the mixture was reacted at -40°C for 1 hour. Triethylamine (0.70 mL) was then added to stop the reaction, and saturated sodium bicarbonate aqueous solution (10 mL) was added to separate the organic layer. The aqueous layer was extracted with dichloromethane (10 mL x 2), and the organic layers were combined and dried over sodium sulfate. The solvent was then removed under reduced pressure. The resulting crude product was purified by silica gel flash chromatography (hexane-ethyl acetate = 9:1 to 3:1) to obtain compound (M8) (0.15 g, 60%) as a white powder. A sample of the obtained compound was used for the in vitro assay by HPLC (COSMOSIL 5C). ８ -MSII, 20mmi. d. , MeCN / H ２ Further purification was performed using a solution with O = 80 / 20. [Compound (M8)] １ H-NMR (CDCl ３ ) δ: 0.78 (s, 3H), 0.80 (s, 3H), 0.82 (d, J=6.7Hz, 3H), 0.94 (s, 3H), 1.01 (s, 3H), 1.20- 1.34 (m, 4H), 1.37-1.46 (m, 3H), 1.58-1.80 (m, 10H), 1.90-2.08 (m, 4H), 2.19 (m, 1H), 2 .. 21 (ddd, J = 15.4, 9.2, 7.2 Hz, 1H), 2.30 (brd, J = 18.2 Hz, 1H), 2.38 (ddd, J = 15.4, 9.5, 5 .2Hz, 1H), 2.48 (m, 1H), 3.12 (brd, J=14.1Hz, 1H), 3.67 (s, 3H), 3.72 (d, J=5.6Hz, 1H). １３ C-NMR (CDCl ３ ) δ: 13.5, 15.5, 17.1, 22.9, 22.4, 23.4, 24.2, 25.2, 25.7, 27.9, 32.3, 32.7, 33.4, 33.7, 35 .8, 36.6, 38.9, 39.9, 45.1, 45.6, 48.4, 48.6, 51.6, 55.3, 84.9, 90.5, 123.7, 132.1, 174.8. HRMS-ESI (m / z): [M+H] ＋ calcd for C２８ H ４５ O ３ , 429.3363; found, 429.3364.

[0043] Synthesis Example 6: Synthesis of Compound (M8) A solution of compound (M7) (22 mg, 0.050 mmol) in 1,1,1,3,3,3-hexafluoro-2-propanol (1.0 mL) was stirred at 70°C for 24 hours, and then the solution was concentrated. The resulting crude product was purified by silica gel flash chromatography (hexane-ethyl acetate = 9:1 to 2:1) to obtain a mixture of compound (M8) and compound (M9) (16.6 mg, compound (M8):compound (M9) = 36:64). The resulting mixture was subjected to HPLC (COSMOSIL 5C) in three parts. ８ -MSII, 20mmi. d. , MeCN:H ２ The compounds were purified using a method (O=80:20) to obtain compound (M8) (4.7 mg, 22%) and compound (M9) (9.2 mg, 43%), respectively. [Compound (M9)] １ H-NMR (CDCl ３ ) δ: 0.77 (s, 3H), 0.84 (s, 3H), 0.86 (d, J=6.7Hz, 3H), 0.94 (s, 3H), 1.00 (s, 3H), 1.15-1 .30 (m, 4H), 1.38-1.49 (m, 5H), 1.50-1.81 (m, 7H), 1.82-1.96 (m, 3H), 2.14 (m, 1H), 2.2 3 (ddd, J=15.3, 10.7, 6.0Hz, 1H), 2.40 (ddd, J=15.3, 11.1, 4.9Hz, 1H), 2.56 (brd, J=16 0Hz, 1H), 2.48 (m, 1H), 3.15 (brd, J=13.8Hz, 1H), 3.66 (s, 3H), 3.73 (d, J=5.6Hz, 1H). １３ C-NMR (CDCl ３ ) δ: 16.1, 20.2, 23.3, 23.4, 25.3, 25.6, 28.5, 28.8, 29.7, 31.6, 33.6, 35.9, 36.1 , 36.3, 36.8, 44.6, 45.3, 49.4, 51.753.1, 54.6, 85.0, 90.1, 123.2, 132.7, 174.8. HRMS-ESI (m / z): [M+H] ＋calcd for C ２８ H ４５ O ３ , 429.3363; found, 429.3365.

[0044] Synthesis Example 7: Synthesis of Compound (M5)

[0045] To a solution of compound (M4) (0.12 g, 0.2 mmol) in tert-butyl alcohol (30 mL), 100 mL of 0.10 mM ethylenediaminetetraacetic acid disodium aqueous solution, sodium bicarbonate (0.25 g, 3.0 mmol), and oxone (0.62 g, 1.0 mmol) were added in sequence, and the mixture was vigorously stirred at room temperature for 1 hour. Then, sodium bicarbonate (0.25 g, 3.0 mmol) and oxone (0.62 g, 1.0 mmol) were added, and the mixture was vigorously stirred at room temperature for 1 hour. The solution was diluted with purified water (50 mL), extracted with dichloromethane (20 mL x 3), dried over sodium sulfate, and the solvent was removed under reduced pressure. The resulting crude product was dissolved in N,N-dimethylformamide (20 mL), and triethylamine (0.40 mL, 2.9 mmol) and tert-butyldimethylsilyl chloride (0.17 g, 1.1 mmol) were added, followed by stirring at room temperature for 4 hours. Diethyl ether (10 mL) and purified water (20 mL) were added and partitioned. The aqueous layer was further extracted with diethyl ether (10 mL), and the organic layers were washed together with saturated brine. After drying over sodium sulfate, the solvent was removed under reduced pressure. The resulting crude product was purified by silica gel flash chromatography (hexane-ethyl acetate = 20:1) to obtain compound (S1) (79 mg). Compound (S1) was dissolved in dichloromethane (11 mL), and 70% metachloroperbenzoic acid (0.14 g, 0.55 mmol) was added and the mixture was stirred at room temperature for 5 days. Saturated sodium bicarbonate aqueous solution (10 mL) and 10% sodium thiosulfate aqueous solution (10 mL) were added and the mixture was stirred for a while. Then, it was extracted with dichloromethane (10 mL x 2), dried over sodium sulfate, and the solvent was removed under reduced pressure. The crude product obtained was purified by silica gel flash chromatography (hexane-dichloromethane-ethyl acetate = 5:5:2) to obtain compound (M5) (50 mg, three-step yield 50%) as a grayish-white solid. [Compound (S1)]１ H-NMR (CDCl ３ ): δ: 0.17 (s, 6H), 0.44 (d, J = 4.2 Hz, 1H), 0.63 (d, J = 4.2 Hz, 1H), 0.82 (td, J = 12.6, 2 Hz, 1H), 0.87 (d, J = 6.7 Hz, 1H), 0.93 (s, 3H), 0.96 (s, 9H), 1.05 (s, 3H), 1.13 (s, 3H), 1.13 - 1.21 (m, 3H), 1.24 (s, 3H), 1.24 - 1.35 (m, 4H), 1.35 - 1.53 (m, 5H), 1.60 - 1.80 (m, 5H), 1.86 - 2.05 (m, 5H), 2.08 - 2.17 (m, 2H), 2.23 (brd, J = 14.5 Hz, 1H), 4.82 (dd, J = 11.2, 4.5 Hz, 1H), 5.39 (dd, J = 8.1, 6.5 Hz, 1H), 7.44 (m, 2H, Bz), 7.56 (m, 1H, Bz), 8.06 (m, 2H, Bz). HRMS-ESI (m / z): [M - OH] ＋ calcd for C ４１ H ６０ F ３ O ３ Si, 685.4258; found, 685.4258. HRMS-ESI (m / z): [M - OBz] ＋ calcd for C ３４ H ５６ F ３ O ２ Si, 581.3996; found, 581.3994. [Compound (M5)] １ H-NMR (CDCl ３) δ: 0.45 (d, J=4.2Hz, 1H), 0.62 (d, J=4.2Hz, 1H), 0. 84 (ddd, J=12.7, 12.7, 2Hz, 1H), 0.93 (s, 3H), 1.05 ( s, 3H), 1.08-1.23 (m, 2H), 1.11 (d, J=6.7Hz, 1H), 1. 16 (s, 3H), 1.26-1.37 (m, 2H), 1.40-1.62 (m, 6H), 1.6 2-1.80 (m, 3H), 1.94 (m, 1H), 2.06 (d, J=16.6Hz, 1H) , 2.06-2.20 (m, 4H), 2.45 (quin, J = 6.7Hz, 1H), 2.75 ( dd, J=16.6, 6.5Hz, 1H), 4.83 (dd, J=11.2, 4.6Hz, 1H ), 7.44 (m, 2H, Bz), 7.56 (m, 1H, Bz), 8.06 (m, 2H, Bz). １３ C-NMR (CDCl ３ ) δ: 15.6, 17.5, 20.1, 20.3, 20.6, 21.1, 25.2, 2 5.7, 25.9, 26.1, 26.3, 27.0, 30.1, 31.8, 35.9, 3 8.9, 39.4, 40.0, 41.3, 47.4, 49.4, 50.1, 81.3, 9 9.6, 128.5, 129.7, 131.1, 132.9, 166.4, 177.4. HRMS-ESI (m / z): [M+H] ＋ calcd for C ３３ H ４５ O ４ , 505.3312; found, 505.3309.

[0046] Synthesis Example 8: Synthesis of Compound (M6) Compound (M5) (11 mg, 0.022 mmol) was dissolved in ethanol (4.0 mL), and saturated potassium hydroxide aqueous solution (2.0 mL) was added dropwise while cooling to 0°C, followed by stirring at room temperature for 18 hours. 50% acetic acid aqueous solution (6.0 mL) was added dropwise over 20 minutes, followed by extraction with ethyl acetate (10 mL x 3). The resulting organic layer was washed with saturated brine, dried over sodium sulfate, and the solvent was removed under reduced pressure. The crude product was dissolved in methanol (4.0 mL), trimethylsilyldiazomethane (2.0 M in hexane, 0.45 mL, 0.90 mmol) was added, and the mixture was stirred at room temperature for 30 minutes, followed by removal of the solvent under reduced pressure. The crude product obtained (compound (S2)) was dissolved in dichloromethane (2.0 mL), and boron trifluoride diethyl ether complex (20 μL, 0.16 mmol) was added dropwise at -40°C. The reaction was then allowed to proceed at -40°C for 1 hour, and triethylamine (22 μL) was added to stop the reaction. Then, saturated sodium bicarbonate aqueous solution (5.0 mL) was added to separate the organic layer. The aqueous layer was extracted with dichloromethane (5.0 mL x 2), and the organic layers were combined and dried over sodium sulfate. The solvent was then removed under reduced pressure. The obtained crude product was purified by silica gel flash chromatography (hexane-ethyl acetate = 15:1 to 10:1) to obtain compound (M6) (2.7 mg, three-step yield 30%) as a white powder. [Compound (M6)] １ H-NMR (CDCl ３ ) δ: 0.79 (s, 3H), 0.83 (s, 3H), 0.86 (d, J = 6.6Hz, 3H), 0.93 (s, 3H), 1.01 (s, 3H), 1.20-1.37 (m , 4H), 1.37-1.46 (m, 3H), 1.49 (dd, J = 12.2, 6.4Hz, 1H), 1.60-1.78 (m, 8H), 1.94 (ddd, J = 12.7, 8.9, 4.7Hz, 3H), 2.00 (dd, J=14.4, 11.7Hz, 1H), 2.02 (m, 1H), 2.12-2.36 (m, 3H), 2.48 (m, 1H) , 2.58 (dd, J=14.4, 2.2Hz, 1H), 3.12 (brd, J=14.3Hz, 1H), 3.66 (s, 3H), 3.73 (d, J=5.6Hz, 1H). １３ C-NMR (CDCl ３) δ: 13.6, 16.5, 17.1, 22.8, 23.3, 24.1, 25.1, 25.7, 32.1, 33.4, 33.6, 35.7, 36.5, 37 3, 38.1, 38.4, 45.0, 45.5, 47.7, 48.5, 51.7, 55.2, 84.9, 90.5, 123.5, 132.0, 174.4. HRMS-ESI (m / z): [M+H] ＋ calcd for C ２７ H ４３ O ３ , 415.3207; found, 415.3209.

[0047] Synthesis Example 9: Synthesis of Compound (I) Compound (M6) (2.7 mg, 6.5 μmol) was dissolved in ethanol (2.0 mL), and saturated potassium hydroxide aqueous solution (1.0 mL) was added dropwise while cooling to 0°C. The mixture was then stirred at room temperature for 10 hours. 50% acetic acid aqueous solution (3.0 mL) was added dropwise over 20 minutes, followed by extraction with ethyl acetate (5.0 mL x 3). The resulting organic layer was washed with saturated brine, dried over sodium sulfate, and the solvent was removed under reduced pressure. The crude product was then analyzed by HPLC (COSMOSIL 5C). １８ -MSII, 10mmi. d. , MeCN:H ２ Compound (I) (1.5 mg, 58%) was obtained by purification using a method (O=50:50 to 100:0). [Compound (I)] １ H-NMR (acetone-d ６ ) δ: 0.84 (s, 3H), 0.87 (s, 3H), 0.89 (d, J=6.7Hz, 3H), 0.91 (s, 3H), 1.01 (s, 3H), 1.26-1.31 (m, 2H), 1.31-1.41 (m, 2H), 1.41-1.49 (m, 2H), 1.55- 1.77 (m, 8H), 1.90-2.03 (m, 3H), 2.14-2.36 (m, 4H), 2.53 (m, 1H), 2.59 (d d, J=14.6, 1.9Hz, 1H), 3.07 (brd, J=14.0Hz, 1H), 3.64 (d, J=5.5Hz, 1H). １３ C-NMR (acetone-d ６) δ: 13.7, 16.7, 17.4, 23.3, 23.4, 24.6, 25.0, 26.1, 32.7, 33.9, 34.2, 36.4, 37.2, 37.8, 38 2, 39.0, 45.7, 46.0, 48.2, 49.1, 49.6, 49.7, 55.8, 79.2, 85.0, 90.7, 124.1, 132.5, 174.5. HRMS-ESI (m / z): [M+H] ＋ calcd for C ２６ H ４１ O ３ , 401.3050; found, 401.3047.

[0048] Synthesis Example 10: Synthesis of Compound (M10) To a solution of compound (M8) (43 mg, 0.10 mmol) in dichloromethane (1.0 mL), aluminum diisobutylhydride (1.0 M in toluene, 0.40 mL, 0.40 mmol) was added dropwise at 0°C and the mixture was stirred for 30 minutes. 5.0 mL of 1.0 M aqueous potassium sodium tartrate solution was added and the mixture was stirred for a while before extraction with dichloromethane (5.0 mL x 3). The organic layers were washed together with purified water (10 mL), dried over sodium sulfate, and the solvent was removed under reduced pressure to obtain compound (S3). The obtained compound (S3) was dissolved in dichloromethane (0.5 mL x 2) and added to a solution of dichloromethane (1.0 mL), dimethyl sulfoxide (30 μL, 0.44 mmol), and oxalyl chloride (25 μL, 0.29 mmol) mixed at -78°C for 10 minutes. The mixture was then stirred for a further 1.5 hours. Triethylamine (0.12 mL, 0.87 mmol) was added to the reaction solution at -78°C, and the mixture was stirred while slowly raising the temperature to room temperature. After 1 hour, saturated ammonium chloride aqueous solution (5 mL) was added, followed by extraction with diethyl ether (5 mL x 2). The organic layers were then washed sequentially with 1 M hydrochloric acid (5 mL) and saturated brine (5 mL), dried over sodium sulfate, and the solvent was removed under reduced pressure. The resulting crude product was purified by silica gel flash chromatography (hexane-ethyl acetate = 10:1) to obtain compound (M10) (58 mg, two-step yield 58%) as a white solid. [Compound (M10)] １ H-NMR (CDCl ３) δ: 0.77 (s, 3H), 0.81 (s, 3H), 0.82 (d, J=6.7Hz, 3H), 0.93 (s, 3H), 1.0 0 (s, 3H), 1.18-1.34 (m, 4H), 1.35-1.47 (m, 3H), 1.55-1.89 (m, 10H), 1. 88-2.09 (m, 4H), 2.29 (m, 1H), 2.34 (m, 1H), 2.42-2.55 (m, 2H), 3.12 (b rd, J=14.2Hz, 1H), 3.72 (d, J=5.6Hz, 1H), 9.78 (dd, J=2.1, 1.6Hz, 1H). １３ C-NMR (CDCl ３ ) δ: 13.7, 15.7, 17.0, 22.8, 23.3, 24.2, 24.8, 25.1, 25.6, 32.3, 33.3, 33.7, 35.7, 36 5, 38.8, 40.0, 42.8, 45.0, 45.5, 48.4, 48.5, 55.1, 84.9, 90.5, 123.6, 132.0, 203.5. HRMS-ESI (m / z): [M+H] ＋ calcd for C ２７ H ４３ O ２ , 399.3258; found, 399.3266.

[0049] Synthesis Example 11: Synthesis of Compound (II) A solution of compound (M10) (13 mg, 0.033 mmol) in tetrahydrofuran (0.5 mL x 2) was added dropwise at 0°C to an excess volume of isopropylidenetriphenylphosphoran in tetrahydrofuran (2.6 mL), and the mixture was heated to room temperature and stirred for 2 hours. A saturated aqueous solution of ammonium chloride (10 mL) was added to the reaction solution, followed by extraction with dichloromethane (10 mL x 2). After drying with sodium sulfate, the solvent was removed under reduced pressure. The resulting crude product was passed through a silica gel short-pass column (dichloromethane) to obtain a crude purified product (13.1 mg). Further HPLC (COSMOSIL 5C) was performed. １８ -MSII, 10mmi. d. , MeOH:H ２ The compound (II) (7.7 mg, 56%) was purified using O = 95:5 (0-30 min) and 100:0 (30-60 min) to obtain compound (II) as a white solid. [Compound (II)] １ H-NMR (CDCl ３)δ:0.75(s,3H),0.77(s,3H),0.82(d,J=6.8Hz,3H),0.93(s,3H),1.01(s,3H),1.23(d,J=12.5Hz,1H),1.27(m,1H),1.33-1.47(m,3H),1.50-1.78(m,14H),1.60(s,3H),1.68(s,3H),1.83(m,1H),1.94(ddd,J=12.7,9.0,4.7Hz,1H),1.94-2.09(m,3H),2.17(m,1H),2.29(brd,J=18.8Hz,1H),2.46(m,1H),3.12(brd,J=13.9Hz,1H),3.73(d,J=5.6Hz,1H),5.11(brt,J=7.1Hz,1H). １３ C-NMR(CDCl ３ )δ:13.6,15.8,17.2,17.8,22.8,23.3,14.2,25.2,25.6,25.9,26.5,32.3,32.7,33.4,33.8,35.8,36.5,38.9,40.1,45.0,45.5,48.3,48.6,55.2,84.9,90.5,123.5,125.2,131.3,132.2. HRMS-ESI(m / z):[M+H] ＋ calcd for C ３０ H ４９ O,425.3778;found,425.3788.

[0050] Test Example 1: Hatching Inducing Activity Test The hatching-inducing activity of compounds (I) and (II) was evaluated using the following procedure. Potato cyst nematodes (PCN, Globodera rostochiensis) and soybean cyst nematodes (SCN, Heterodera glycines) were used in this test, and the following procedures were performed separately for each nematode. Dry soil containing each cyst was stored in a low-temperature room at 4°C. Cysts were collected using a sieve to remove excess sand and debris, wrapped in damp filter paper, and stored at 4°C until immediately before use. The required amount of cysts was taken into purified water and allowed to absorb water in a cool, dark place for one week. After cracking the cysts and removing the contained eggs, the eggs were allowed to settle by centrifugation. The supernatant was pipetted to remove as much cyst shell and debris as possible. Purified water was added again to suspend the mixture, and then centrifugation and removal of the supernatant were performed. The eggs were again suspended in purified water, dispensed into Eppendorf tubes, centrifuged, and the supernatant was removed. Aqueous solutions of the test compound at various concentrations (1000, 10, 0.1 nM) were prepared by serially diluting the DMSO solution with purified water. 300 μL of each solution was added to the Eppendorf tubes containing the eggs for suspension, and then 100 μL was dispensed into 96-well plates. As positive controls, tomato hydroponic solution diluted with purified water was used for potato cyst nematodes, and root extract of Lotus corniculatus diluted with purified water was used for soybean cyst nematodes. As a negative control, DMSO without the compound diluted with purified water was used. The number of eggs and juveniles at the start was counted, and the N values ​​were determined accordingly. Ｅ０ and N Ｊ０ The plates were shielded from light with aluminum foil, and the PCN was incubated at 27°C and the SCN at 25°C. After 7 days and 14 days, the number of larvae was counted, and the N values ​​were determined accordingly. Ｊ７ and N Ｊ１４ The hatching rate was calculated using the following formula.

[0051] Figure 1 shows the results of the hatching-inducing activity test of compound (I) against PCN. Figure 2 shows the results of the hatching-inducing activity test of compound (I) against SCN. Figure 3 shows the results of the hatching-inducing activity test of compound (II) against PCN. Figure 4 shows the results of the hatching-inducing activity test of compound (II) against SCN. From these results, it can be understood that compounds (I) and (II) are compounds that exhibit hatching-inducing activity against cyst nematodes.

[0052] The polycyclic compound of the present invention exhibits hatching-inducing activity against cyst nematodes and is useful as an active ingredient in cyst nematode control agents.

Claims

1. Formula (A) [In the formula, R １ is a carboxyl group or CH ２ CH = C(CH ３ ) ２ A polycyclic compound represented by [ ].

2. Equation (I) The polycyclic compound according to claim 1, represented as shown in the image.

3. The polycyclic compound according to claim 1, represented by formula (II). ​ 4. Formula (M1) The compound represented by formula (M2) A step of converting the compound represented by formula (M2) to a compound represented by formula (M4) A step of converting the compound represented by formula (M4) to a compound represented by formula (M5) A step of converting the compound represented by formula (M5) to a compound represented by formula (M6) A method for producing a polycyclic compound according to claim 2, comprising the steps of: converting to a compound represented by formula (M6); and converting the compound represented by formula (M6) to a polycyclic compound represented by formula (I).

5. Formula (M1) The compound represented by formula (M2) A step of converting the compound represented by formula (M2) to a compound represented by formula (M4) A step of converting the compound represented by formula (M4) to a compound represented by formula (M7) A step of converting the compound represented by formula (M7) to a compound represented by formula (M8) A step of converting the compound represented by formula (M8) to a compound represented by formula (M10) A method for producing a polycyclic compound according to claim 3, comprising the steps of: converting to a compound represented by formula (M10); and converting the compound represented by formula (M10) to a polycyclic compound represented by formula (II).

6. A cyst nematode control agent comprising the polycyclic compound described in claim 1.

7. A method for controlling cyst nematodes, comprising applying an effective amount of the polycyclic compound described in claim 1 or the cyst nematode control agent described in claim 6 to a habitat of cyst nematodes.

Images