Plant anthracnose control agent comprising a fatty acid derivative or a salt thereof

Abstract

To provide a novel control agent for anthracnose in plants. [Solution] A plant anthracnose control agent comprising a fatty acid derivative represented by the following formula (1) or a salt thereof: JPEG2026136928000008.jpg51152 (In formula (1), R 1 R represents an alkyl group substituted with a hydroxyl group. 2 R represents a hydrogen atom or an optionally substituted alkyl group, 3 ) represents an alkyl group with 11 to 17 carbon atoms.

Description

[Technical Field]

[0001] The present invention relates to a plant anthracnose control agent comprising a fatty acid derivative or a salt thereof. [Background technology]

[0002] Plants are susceptible to various diseases not only from physical and environmental stresses such as soil conditions, weather conditions, and pollutants, but also from pathogens and pests such as filamentous fungi, bacteria, and viruses. For example, anthracnose, caused by fungi of the genus Colletotrichum, affects a wide range of plants, from horticultural crops such as fruit trees, vegetables, and flowers, to trees and turfgrass. When infected with anthracnose fungus, circular lesions ranging from grayish-brown to blackish-brown appear on the leaves and fruits, eventually causing the plant to wither and die (Non-Patent Literature 1). Chemically synthesized fungicides such as benzimidazole and strobilurin are widely used to control anthracnose in plants.

[0003] On the other hand, fatty acid derivatives such as fatty acid amides are known to be used in the food and cosmetics industries as emulsifiers, lubricants, and surfactants, and have no environmental impact.

[0004] However, there have been no reports on the relationship between fatty acid derivatives such as fatty acid amides and the control of anthracnose in plants. [Prior art documents] [Non-patent literature]

[0005] [Non-Patent Document 1] Yoshihiko Hirayama et al., Plant Protection, 2019, Vol.4, pp.43-48 [Overview of the Initiative]

[0006] The inventors have discovered that fatty acid derivatives such as fatty acid amides suppress the germination of anthracnose fungal spores and are useful for controlling anthracnose in plants. This invention is based on this finding.

[0007] The object of the present invention is to provide a new technical means for controlling anthracnose of plants.

[0008] According to the present invention, the following inventions are provided. [1] A plant anthracnose control agent comprising a fatty acid derivative represented by the following formula (1) or a salt thereof: [Chemical formula] (In formula (1), R 1 represents an alkyl group substituted with a hydroxy group, R 2 represents a hydrogen atom or an optionally substituted alkyl group, R 3 represents an alkyl group having 11 to 17 carbon atoms.). [2] The plant anthracnose control agent according to [1], wherein R 1 is an alkyl group having 1 to 5 carbon atoms substituted with a hydroxy group, R 2 is a hydrogen atom, and R 3 is an alkyl group having 11 to 13 carbon atoms. [3] The plant anthracnose control agent according to [1] or [2], wherein R 1 is a group represented by the following formula (2) [Chemical formula] [4] The plant anthracnose control agent according to any one of [1] to [3], wherein the anthracnose control includes inhibition of germination of anthracnose spores. [5] The plant anthracnose control agent according to any one of [1] to [4], wherein the anthracnose is anthracnose caused by a fungus of the genus Colletotrichum. [6] A method for controlling anthracnose of plants, comprising the step of applying the plant anthracnose control agent according to any one of [1] to [5] to cultivation soil or plants. ​[7] The method for controlling anthracnose of the plant according to [6], wherein the plant is at least one plant selected from the group consisting of Cucurbitaceae plants, Solanaceae plants, Rosaceae plants, Urticaceae plants, Caricaceae plants, Bignoniaceae plants, Poaceae plants, Fabaceae plants, Brassicaceae plants, Musaceae plants, and Asteraceae plants. [8] The method for controlling anthracnose of the plant according to [6] or [7], wherein the control of anthracnose includes inhibition of germination of anthracnose spores.

[0009] According to the present invention, there is provided an agent for controlling anthracnose of plants. Further, according to the present invention, it is also possible to provide an agent (preferably, an agent for controlling anthracnose) for inhibiting the germination of anthracnose spores.

Brief Description of the Drawings

[0010] [Figure 1] Figure 1 is a diagram showing the germination rate of the spores after mixing fatty acid derivative 1 with a suspension of anthracnose spores of cucurbits and incubating for 24 hours. Detailed Description of the Invention

[0011] One feature of the present invention is that it is an agent for controlling anthracnose of plants (hereinafter, also referred to as the anthracnose control agent of the present invention) containing a fatty acid derivative represented by formula (1) or a salt thereof.

[0012] <Fatty acid derivative represented by formula (I) or a salt thereof> The fatty acid derivative of the present invention has the following formula (1):

Chemical formula

[0013] In formula (1), R 1 represents an alkyl group substituted with a hydroxy group, R 2 represents a hydrogen atom or an alkyl group which may be substituted, R 3 represents an alkyl group having 11 to 17 carbon atoms.

[0014] R in equation (1) 1 Examples of alkyl groups represented by include linear or branched alkyl groups having 1 to 10 carbon atoms, and preferably linear or branched alkyl groups having 1 to 5 carbon atoms. 1 Specific examples of alkyl groups represented by include methyl group, ethyl group, propyl group (e.g., n-propyl group, i-propyl group), butyl group (e.g., n-butyl group, i-butyl group, s-butyl group, tert-butyl group), pentyl group, 1-methylbutyl group, 1-ethylpropyl group, 2-methylbutyl group, 3-methylbutyl group, 1,1-dimethylpropyl group, 1,2-dimethylpropyl group, and 2,2-dimethylpropyl group, with methyl group, ethyl group, propyl group, butyl group, or pentyl group being preferred.

[0015] R in equation (1) 1 The alkyl group represented by is substituted with at least one hydroxyl group. 1 Specific examples of alkyl groups substituted with a hydroxyl group that are represented by include, for example, hydroxymethyl group, 1-hydroxyethyl group, 2-hydroxyethyl group, 1-hydroxy-n-butyl group, 2-hydroxy-n-propyl group, 4-hydroxybutyl group, and hydroxy-tert-butyl group (for example, the group represented by the chemical formula (2) below), and preferably the group represented by the chemical formula (2) below. [ka] (In the chemical formula (2), the wavy lines indicate bonds with nitrogen.)

[0016] In formula (1), R 2 represents a hydrogen atom or an optionally substituted alkyl group, preferably a hydrogen atom.

[0017] R in equation (1) 2 Examples of alkyl groups represented by include linear or branched alkyl groups having 1 to 10 carbon atoms, and preferably linear or branched alkyl groups having 1 to 5 carbon atoms. 1Specific examples of alkyl groups represented by include methyl group, ethyl group, propyl group (e.g., n-propyl group, i-propyl group), butyl group (e.g., n-butyl group, i-butyl group, s-butyl group, tert-butyl group), pentyl group, 1-methylbutyl group, 1-ethylpropyl group, 2-methylbutyl group, 3-methylbutyl group, 1,1-dimethylpropyl group, 1,2-dimethylpropyl group, and 2,2-dimethylpropyl group. Preferably, the alkyl group is methyl group, ethyl group, propyl group, butyl group, pentyl group, or 1,1-dimethylpropyl group.

[0018] R in equation (1) 2 The alkyl group represented by may be substituted, and examples of such substituents include hydroxyl groups. 2 A specific example of an alkyl group that may be substituted, represented by , is the group represented by the chemical formula (2) below. [ka] (In the chemical formula (2), the wavy lines indicate bonds with nitrogen.)

[0019] R in equation (1) 3 The alkyl group having 11 to 17 carbon atoms represented by represents a linear or branched alkyl group having 11 to 17 carbon atoms, preferably a linear or branched alkyl group having 11 to 13 carbon atoms. Specific examples of alkyl groups having 11 to 17 carbon atoms include undecyl group, dodecyl group, tridecyl group, tetradecyl group, pentadecyl group, hexadecyl group, heptadecyl group, isopalmityl group, isostearyl group, and 2-decyltetradecyl group, with undecyl group being preferred.

[0020] The salt of the fatty acid derivative represented by formula (1) is preferably an agriculturally permissible salt. Examples of such salts include salts composed of a hydroxyl group, a carboxyl group, a group having a nitrogen atom (e.g., an amino group), etc., in the structure of the fatty acid derivative represented by formula (1), and a metal or organic base, or a mineral acid or organic acid. Examples of the metal include alkali metals such as sodium and potassium, or alkaline earth metals such as magnesium and calcium. Examples of the organic base include triethylamine and diisopropylamine. Examples of mineral acids include phosphoric acid, hydrochloric acid, hydrobromic acid, hydroiodic acid, boric acid, and sulfuric acid. Examples of organic acids include formic acid, acetic acid, lactic acid, ascorbic acid, succinic acid, fumaric acid, maleic acid, oxalic acid, citric acid, benzoic acid, salicylic acid, tartaric acid, methanesulfonic acid, 4-toluenesulfonic acid, trifluoromethanesulfonic acid, and trifluoroacetic acid.

[0021] In the fatty acid derivative represented by formula (1), R 1 , R 2 , R 3 According to a preferred embodiment relating to the combination of R 1 R is a group represented by the chemical formula (2), 2 is a hydrogen atom, R 3 This is a linear or branched alkyl group having 11 to 13 carbon atoms, more preferably a linear alkyl group having 11 to 13 carbon atoms, and even more preferably a linear alkyl group having 11 carbon atoms.

[0022] A more preferred embodiment of the fatty acid derivative represented by formula (1) above is N-(2-hydroxy-1,1-dimethylethyl)dodecaneamide.

[0023] The fatty acid derivative of the present invention may be a commercially available product, or a chemically synthesized product produced by a conventional chemical synthesis method can be used.

[0024] <Method for producing fatty acid derivatives> According to one embodiment of the present invention, R in a fatty acid derivative represented by formula (1) 1 , R 2 , R 3 The combination is R 1 The group is represented by the chemical formula (2), and R 2 R is a hydrogen atom, 3 A method for producing a fatty acid derivative represented by formula (1), where is a linear or branched alkyl group having 11 to 13 carbon atoms, includes a reaction step of synthesizing the fatty acid derivative represented by formula (1) by reacting 2-amino-2-methyl-1-propanol with a fatty acid chloride having 12 to 14 carbon atoms. In the above reaction step, the presence of triethylamine is preferable.

[0025] 2-amino-2-methyl-1-propanol is preferably dissolved in a solvent (preferably pyridine). The fatty acid chloride with 12 to 14 carbon atoms is preferably dissolved in a solvent (preferably dichloromethane).

[0026] The temperature for reacting 2-amino-2-methyl-1-propanol with a fatty acid chloride having 12 to 14 carbon atoms is not particularly limited, but is preferably 0 to 50°C, and more preferably room temperature to 40°C. Here, room temperature refers to 20 to 30°C.

[0027] The reaction time between 2-amino-2-methyl-1-propanol and a fatty acid chloride having 12 to 14 carbon atoms is not particularly limited, but is, for example, 0.1 to 10 days, preferably 1 to 3 days.

[0028] <A plant anthracnose control agent comprising a fatty acid derivative or a salt thereof represented by formula (1)> The anthracnose control agent of the present invention may use the fatty acid derivative or a salt thereof as the active ingredient alone, but it is generally used in a form convenient for use (e.g., dosage form) according to conventional methods for agricultural chemical formulation. That is, the fatty acid derivative or a salt thereof of the present invention can be mixed with an appropriate inert carrier in an appropriate ratio, together with an auxiliary agent as needed, and then dissolved, separated, suspended, mixed, impregnated, adsorbed or attached to it to be formulated into an appropriate dosage form, such as a suspension, emulsion, liquid, wettable powder, granular wettable powder, granules, powder, tablet, pack, etc., and used.

[0029] The anthracnose control agent of the present invention may contain, as necessary, additive components commonly used in pesticide formulations, in addition to the fatty acid derivative or salt thereof of the present invention used as the active ingredient. Examples of such additive components include carriers such as solid carriers and liquid carriers, surfactants, dispersants, wetting agents, binders, tackifiers, thickeners, colorants, spreading agents, adsorbents, antifreeze agents, anticaking agents, disintegrants (or disintegration accelerators), decomposition inhibitors, and preservatives. These additive components may be used individually or in combination of two or more.

[0030] Examples of solid carriers include natural minerals such as quartz, clay, kaolinite, pyrophyllite, sericite, talc, bentonite, acid clay, attapulgite, zeolite, and diatomaceous earth; inorganic salts such as calcium carbonate, ammonium sulfate, sodium sulfate, and potassium chloride; organic solid carriers such as synthetic silicic acid, synthetic silicates, starch, cellulose, and plant powders (e.g., sawdust, coconut husk, corn cob, tobacco stalk, etc.); plastic carriers such as polyethylene, polypropylene, and polyvinylidene chloride; urea, inorganic hollow bodies, plastic hollow bodies, and fumed silica. These may be used individually or in combination of two or more.

[0031] Examples of liquid carriers include monohydric alcohols such as methanol, ethanol, propanol, isopropanol, and butanol; polyhydric alcohols such as ethylene glycol, diethylene glycol, propylene glycol, hexylene glycol, polyethylene glycol, polypropylene glycol, and glycerin; polyhydric alcohol compounds such as propylene glycol ether; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, and cyclohexanone; ethers such as ethyl ether, dioxane, ethylene glycol monoethyl ether, dipropyl ether, and tetrahydrofuran; and n-paraffin. Examples include aliphatic hydrocarbons such as naphthenes, isoparaffins, kerosene, and mineral oil; aromatic hydrocarbons such as benzene, toluene, xylene, solvent naphtha, and alkylnaphthalene; halogenated hydrocarbons such as dichloromethane, chloroform, and carbon tetrachloride; esters such as ethyl acetate, diisopropyl phthalate, dibutyl phthalate, dioctyl phthalate, and dimethyl adipate; lactones such as γ-butyrolactone; amides such as dimethylformamide, diethylformamide, dimethylacetamide, and N-alkylpyrrolidinone; nitriles such as acetonitrile; sulfur compounds such as dimethyl sulfoxide; vegetable oils such as soybean oil, rapeseed oil, cottonseed oil, and castor oil; and water. These may be used individually or in combination of two or more.

[0032] The surfactants are not particularly limited, but examples include nonionic surfactants, anionic surfactants, cationic surfactants, and amphoteric surfactants. Examples of nonionic surfactants include sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters, sucrose fatty acid esters, polyoxyethylene fatty acid esters, polyoxyethylene resin acid esters, polyoxyethylene fatty acid diesters, polyoxyethylene alkyl ethers, polyoxyethylene alkylaryl ethers, polyoxyethylene alkylphenyl ethers, polyoxyethylene dialkylphenyl ethers, polyoxyethylene alkylphenyl ether formalin condensates, polyoxyethylene polyoxypropylene block copolymers, polystyrene polyoxyethylene block polymers, alkyl polyoxyethylene polypropylene block copolymer ethers, polyoxyethylene alkylamines, polyoxyethylene fatty acid amides, polyoxyethylene fatty acid bisphenyl ethers, polyalkylene benzylphenyl ethers, polyoxyalkylene styrylphenyl ethers, acetylenediol, polyoxyalkylene-added acetylenediol, polyoxyethylene ether-type silicones, ester-type silicones, fluorinated surfactants, polyoxyethylene castor oil, and polyoxyethylene hydrogenated castor oil. Examples of anionic surfactants include alkyl sulfates, polyoxyethylene alkyl ether sulfates, polyoxyethylene alkylphenyl ether sulfates, polyoxyethylene styrylphenyl ether sulfates, alkylbenzene sulfonates, alkylaryl sulfonates, lignin sulfonates, alkyl sulfosuccinates, naphthalene sulfonates, alkylnaphthalene sulfonates, salts of formalin condensates of naphthalene sulfonic acid, salts of formalin condensates of alkylnaphthalene sulfonic acid, fatty acid salts, polycarboxylates, polyacrylates, N-methyl fatty acid sarcosinates, resin salts, polyoxyethylene alkyl ether phosphates, and polyoxyethylene alkylphenyl ether phosphates.Cationic surfactants include sodium laurylamine hydrochloride, sodium stearylamine hydrochloride, sodium oleylamine hydrochloride, sodium stearylamine acetate, sodium stearylaminopropylamine acetate, alkyltrimethylammonium chloride, alkyldimethylbenzalkonium chloride, and other alkylamine salts. Amphoteric surfactants include amino acid type or betaine type amphoteric surfactants. The above surfactants can be used as dispersants or wetting agents. These surfactants may be used individually or in combination of two or more types.

[0033] Examples of binders and tackifiers include carboxymethylcellulose and its salts, dextrin, water-soluble starch, xanthan gum, guar gum, sucrose, polyvinylpyrrolidone, acacia gum, polyvinyl alcohol, polyvinyl acetate, sodium polyacrylate, polyethylene glycol with an average molecular weight of 6,000 to 20,000, polyethylene oxide with an average molecular weight of 100,000 to 5,000,000, phospholipids (e.g., cephalin, lecithin, etc.), cellulose powder, dextrin, modified starch, polyaminocarboxylic acid chelate compounds, crosslinked polyvinylpyrrolidone, copolymers of maleic acid and styrenes, (meth)acrylic acid copolymers, half-esters of polymers consisting of polyhydric alcohols and dicarboxylic acid anhydrides, water-soluble salts of polystyrene sulfonic acid, paraffin, terpenes, polyamide resins, polyacrylates, polyoxyethylene, waxes, polyvinyl alkyl ethers, alkylphenol formalin condensates, and synthetic resin emulsions.

[0034] Examples of thickening agents include xanthan gum, guar gum, tung gum, carboxymethylcellulose, polyvinylpyrrolidone, carboxyvinyl polymers, acrylic polymers, starch compounds, water-soluble polymers such as polysaccharides, high-purity bentonite, and inorganic fine powders such as fumed silica.

[0035] Examples of colorants include inorganic pigments such as iron oxide, titanium dioxide, and Prussian blue, as well as organic dyes such as alizarin dyes, azo dyes, and metal phthalocyanine dyes.

[0036] Examples of antifreeze agents include ethylene glycol, diethylene glycol, propylene glycol, and polyhydric alcohols such as glycerin.

[0037] Examples of auxiliary agents for preventing caking or promoting disintegration include polysaccharides such as starch, alginic acid, mannose, and galactose, polyvinylpyrrolidone, fumed silica, ester gum, petroleum resin, sodium tripolyphosphate, sodium hexametaphosphate, metal stearate, cellulose powder, dextrin, copolymers of methacrylate esters, polyvinylpyrrolidone, polyaminocarboxylic acid chelate compounds, sulfonated styrene-isobutylene-maleic anhydride copolymers, and starch-polyacrylonitrile graft copolymers.

[0038] Examples of decomposition inhibitors include desiccants such as zeolite, quicklime, and magnesium oxide; antioxidants such as phenol compounds, amine compounds, sulfur compounds, and phosphoric acid compounds; and ultraviolet absorbers such as salicylic acid compounds and benzophenone compounds.

[0039] Examples of preservatives include potassium sorbate and 1,2-benzothiazolin-3-one. Furthermore, functional spreading agents, activity enhancers such as metabolic degradation inhibitors like piperonyl butoxide, antifreezes such as propylene glycol, antioxidants such as BHT, UV absorbers, and other auxiliary agents may be used as needed.

[0040] The proportion of the fatty acid derivative or salt of the present invention can be adjusted as needed. It can be appropriately selected and used in amounts ranging from 0.0001 to 90 parts by mass in 100 parts by mass of the anthracnose control agent of the present invention. For example, when using a powder, granules, emulsion, or wettable powder, the amount can range from 0.0001 to 50 parts by mass (0.0001 to 50% by mass relative to the total mass of the anthracnose control agent).

[0041] The anthracnose control agent of the present invention may be applied by spraying the fatty acid derivative or salt of the present invention alone, or by diluting the aforementioned formulation containing the fatty acid derivative or salt of the present invention to a suitable concentration with water or the like and spraying it, or by spraying it directly. Furthermore, the anthracnose control agent of the present invention may be used in combination with other fungicides, insecticides, acaricides, nematicides, herbicides, plant growth regulators, fertilizers, etc., as long as it does not interfere with the effects of the present invention.

[0042] The plant anthracnose control agent according to the present invention can be used to control anthracnose in a wide range of plants. Examples of the above-mentioned anthracnose include anthracnose caused by anthracnose fungi of the genus Colletotrichum and Glomerella, and anthracnose caused by pathogens of the same, same, or closely related species as these plant anthracnose fungi, and preferably anthracnose caused by Colletotrichum fungi. The above-mentioned Colletotrichum anthracnose fungi include: the cucurbit anthracnose fungus Colletotrichum orbiculare (also called Colletotrichum lagenarium), the tea anthracnose fungus Colletotrichum theaesinensis, the radish anthracnose fungus Colletotrichum higginsianum, the kidney bean anthracnose fungus Colletotrichum lindemuthianum, the soybean anthracnose fungus Colletotrichum truncatum, and the Western grass anthracnose fungus Colletotrichum graminicola Examples include Colletotrichum graminicola, mango anthracnose fungus Colletotrichum gloeosporioides, citrus anthracnose fungus Colletotrichum gloeosporioides, rose family anthracnose fungus Colletotrichum acutatum, rose family anthracnose fungus Colletotrichum fioriniae, and acerola anthracnose fungus Colletotrichum tropicale, with Colletotrichum orbiculare being preferred.

[0043] The plants to which the plant anthracnose control agent according to the present invention is applied are not particularly limited as long as they do not hinder the effects of the present invention, but examples include cucurbitaceous plants such as cucumbers, melons and watermelons, nightshadeaceous plants such as eggplants, tomatoes and bell peppers, roseaceous plants such as peaches, pears, strawberries and apples, sumacaceous plants such as mangoes and pistachios, papayaceous plants such as papaya, asparagus, grasses such as corn and wheat, legumes such as green beans and soybeans, brassicas such as cabbage and broccoli, bananas and other plants in the Musaceae family, and chrysanthemums such as lettuce and garland chrysanthemum, with cucurbitaceous plants being preferred.

[0044] The anthracnose control agent of the present invention can control anthracnose in plants, and preferably can suppress the germination of anthracnose fungal spores in plants. Therefore, the anthracnose control agent of the present invention can suppress the germination of anthracnose fungal spores. Accordingly, according to one embodiment of the present invention, the anthracnose control agent of the present invention is provided as an agent for suppressing the germination of anthracnose fungal spores. The anthracnose control agent of the present invention can suppress the germination rate of anthracnose fungal spores to, for example, 30% or less, preferably 15% or less, and more preferably 3% or less.

[0045] According to another aspect of the present invention, a method for controlling anthracnose in plants is provided, comprising the step of applying the anthracnose control agent of the present invention to cultivation soil or plants. The anthracnose control agent of the present invention is advantageous in that it is safe for both the environment and human health.

[0046] The present invention provides a method for controlling anthracnose in plants, which involves applying the anthracnose control agent of the present invention to the cultivation soil or plants. Methods for applying the anthracnose control agent of the present invention include contacting the anthracnose control agent with the plant body or plant seeds, or incorporating it into the cultivation soil for planting, thereby contacting the roots or rhizomes of the plants. Specifically, these methods include foliar spraying of the anthracnose control agent onto the plant body, treatment of seedling trays, spraying onto the soil surface, soil mixing after spraying onto the soil surface, injection into the soil, soil mixing after injection into the soil, soil drenching, soil mixing after soil drenching, spraying onto plant seeds, coating onto plant seeds, immersion into plant seeds, or powder coating onto plant seeds.

[0047] The application rate and concentration of the anthracnose control agent of the present invention vary depending on the target plant, the degree of anthracnose occurrence, the formulation of the anthracnose control agent, the application method, and various environmental conditions. However, when spraying or drenching, the amount of the fatty acid derivative or salt of the present invention as an active ingredient is typically 50 to 1,000,000 g per hectare, preferably 100 to 500,000 g per hectare. When treating seeds, the amount used is typically 0.001 to 50 g per kg of seed as an active ingredient, preferably 0.01 to 10 g. When applying the anthracnose control agent of the present invention to plants by foliar spraying, spraying on the soil surface, injecting into the soil, or drenching the soil, it may be diluted to an appropriate concentration on a suitable carrier before treatment. When applying the anthracnose control agent of the present invention to plant seeds, it may be used by diluting it to an appropriate concentration and then immersing, powdering, spraying, or coating the plant seeds with it. When using powdering, spraying, or coating, the amount of the anthracnose control agent of the present invention used is usually about 0.05 to 50% of the dry plant seed mass, preferably 0.1 to 30%, with the fatty acid derivative or salt of the present invention being the active ingredient. However, the amount used is not limited to these ranges and may vary depending on the form of the anthracnose control agent and the type of plant seed being treated. [Examples]

[0048] The present invention will be described in more detail below with reference to manufacturing examples, preparation examples, and test examples, but the technical scope of the present invention is not limited to these examples. Unless otherwise specified, all percentages and ratios used in the present invention are in mass. Unless otherwise specified, the units and measurement methods described herein are in accordance with JIS standards.

[0049] High-purity reaction reagents from Wako Pure Chemical Industries, Tokyo Chemical Industries, or Aldrich were used. The reaction progresses on a TLC plate (silica gel 60, F 254 The color was confirmed by thin-layer chromatography using a Merck (TLC) system. Color development of the TLC plates was performed using a 5% sulfuric acid-ethanol solution, a 5% phosphomolybdate-ethanol solution, ninhydrin colorant, and a UV lamp (λ=254nm). Silica gel column chromatography was performed using silica gel (Wako Gel, 60N, 63-212 μm). 1 ¹H NMR (400Hz) spectra were measured using a JNM-ECS-400 (JEOL Ltd.). Unless otherwise specified, NMR spectra were measured at 25°C using CDCl3 as the solvent. 1 In the 1H NMR spectral data, s = singlet, d = doublet, dd = double doublet, t = triplet, and m = multiplet were abbreviated, and the TMS peak was set to 0 ppm.

[0050] Manufacturing Example 1: Production of Fatty Acid Derivative 1 (N-(2-hydroxy-1,1-dimethylethyl)dodecaneamide) Pyridine (4.57 mL) was added to a round-bottom flask containing 2-amino-2-methyl-1-propanol (131.6 μL, 1.37 mmol) to dissolve the 2-amino-2-methyl-1-propanol. Then, triethylamine (382.3 μL, 2.74 mmol) was added, and the mixture was magnetically stirred in an ice bath at 0°C. Lauric acid chloride (227.3 μL, 0.91 mmol) dissolved in dichloromethane (3.66 mL) was added dropwise, and the mixture was returned to room temperature to initiate the reaction. The progress of the reaction was tracked by TLC (chloroform / methanol = 20 / 1). Two days after the start of the reaction, an excess amount of methanol was added to stop the reaction. Toluene was added, and the mixture was concentrated under reduced pressure, and the residue was vacuum-dried. Further separation and purification were performed by silica gel column chromatography (toluene / ethyl acetate = 2 / 1), and the fraction containing the target compound (fatty acid derivative 1) was collected, concentrated under reduced pressure, and the residue was vacuum-dried to obtain the target compound as a colorless, transparent liquid. 1 H NMR (400MHz, CDCl3):δ 10.05 (s, 1H, -CO-NH-), 5.53 (s, 1H, -OH), 3.6 (s, 2H, -C H 2-OH), 2.18 (t,2H, -CO-C H 2-), 1.62 (m, 2H, -CO-CH2-C H 2-), 1.31 (s, 6H, -C(C H 3)2CH2OH), 1.28 (s, 16H, -CH2-), 0.89 (t, 3H, CH3).

[0051] Preparation Example 1: Preparation of a test solution containing a fatty acid derivative The fatty acid derivative 1 produced in Production Example 1 was dissolved in ethanol to a concentration of 200 μM, sterilized through a 0.20 μm diameter filter, and a test solution was obtained.

[0052] Test Example 1: Investigation of the inhibition of anthracnose fungal spore germination by fatty acid derivatives. The effect of fatty acid derivative 1 from Production Example 1 on the germination of anthracnose fungal spores was measured. The anthracnose fungus used was the cucurbit anthracnose fungus (Colletotrichum orbiculare) strain Co 104-T.

[0053] Preparation of anthracnose fungal spore suspension <Culturing of anthracnose fungus> 19.5g of potato dextrose agar (Nissui Pharmaceutical Co., Ltd.) was dissolved in 500mL of pure water, autoclaved (121°C, 20 minutes), and then dispensed into sterile petri dishes (90mm diameter x 15mm depth) in 25mL portions. The mixture was allowed to solidify at room temperature to prepare PDA agar. Cucurbit anthracnose fungi were taken from a culture medium in which they were growing, along with the culture medium itself, placed on a new PDA agar, and sealed in a plastic bag. The cultures were incubated at 25°C for one week before being used in the experiment.

[0054] <Spore collection and washing> Sterile water was added in 10-15 mL increments to PDA medium in which the anthracnose fungus of cucurbits had grown. Sterile water was added to the mixture, and spores were scraped off using a cotton swab to obtain a spore suspension preliminary solution. The obtained spore suspension preliminary solution was placed in a 50 mL Falcon tube and shaken for 10 seconds to uniformly disperse the spores. This spore suspension preliminary solution was centrifuged at 5,000 g at 4°C for 5 minutes to precipitate the spores. After discarding the supernatant, 10 mL of sterile water was added to resuspend the spores, and this was used as the spore suspension.

[0055] <Counting the number of spores> The spore suspension was moderately diluted and 10 μL was added to a Thoma hemocytometer. The spore count was calculated using a light microscope, and the number of spores per 1 mL of suspension was determined. The final count was 4.0 × 10⁶. 5 A spore suspension was prepared to obtain a 0.2% Bacto yeast extract (Thermo Fisher Scientific) with a spore count / mL.

[0056] Measurement of germination inhibitory activity 10 μL of the test solution containing fatty acid derivative 1 obtained in Preparation Example 1 was mixed with 10 μL of spore suspension to obtain a mixture. The final spore concentration in this mixture was 2.0 × 10⁶. 5The spore count was measured per mL, the final Bacto yeast extract concentration was 0.1%, and the final concentration of fatty acid derivative 1 was 100 μM (test group). As a negative control, 10 μL of 0.2% ethanol solution and 10 μL of spore suspension were mixed to obtain a 0.1% ethanol mixture (negative control group). The mixture was then incubated on a glass slide at 25°C for 24 hours. The number of germinated spores was then confirmed using a light microscope (BX53, Olympus). The same procedure was performed three times for both the test group and the negative control group. The germination rate (mean ± standard deviation) of fatty acid derivative 1 is shown in Figure 1.

Claims

1. A plant anthracnose control agent comprising a fatty acid derivative or a salt thereof represented by the following formula (1): 【Chemistry 1】 (In formula (1), R １ This represents an alkyl group substituted with a hydroxyl group, R ２ This represents a hydrogen atom or an optionally substituted alkyl group. R ３ (This represents an alkyl group with 11 to 17 carbon atoms.)

2. R １ However, R is an alkyl group having 1 to 5 carbon atoms substituted with a hydroxyl group. ２ is a hydrogen atom, R ３ The plant anthracnose control agent according to claim 1, wherein is an alkyl group having 11 to 13 carbon atoms.

3. R １ However, the following equation (2) 【Chemistry 2】 A plant anthracnose control agent according to claim 1 or 2, wherein the group is represented by .

4. The plant anthracnose control agent according to claim 1 or 2, wherein the anthracnose control method includes inhibiting the germination of anthracnose fungal spores.

5. The plant anthracnose control agent according to claim 1 or 2, wherein the anthracnose is anthracnose caused by a fungus of the genus Colletotrichum.

6. A method for controlling anthracnose in plants, comprising the step of applying the plant anthracnose control agent described in claim 1 to the cultivation soil or to the plants.

7. The method for controlling anthracnose in a plant according to claim 6, wherein the plant is at least one plant selected from the group consisting of Cucurbitaceae, Solanaceae, Rosaceae, Anacardiaceae, Papayaaceae, Asparagaceae, Poaceae, Fabaceae, Brassicaceae, Musaceae, and Asteraceae.

8. The method for controlling anthracnose in plants according to claim 6, wherein the anthracnose control method includes suppressing the germination of anthracnose fungal spores.

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