WO2005023770A1 - Salicylic acid derivatives, process for production thereof and disease controllers for agricultural and horticultural use - Google Patents

Abstract

Salicylic acid derivatives represented by the general formula (I·II); a process for the production thereof; and disease controllers for agricultural and horticultural use, containing as the active ingredient the salicylic acid derivatives or salts thereof: (I·II) (wherein X is lower alkyl, lower alkoxy, lower haloalkyl, or halogeno; m is an integer of 0 to 3; when m is 2 or above, X’s may be the same or different from each other; R1 is hydrogen or lower alkyl; and R2 is hydrogen, hydroxyl, halogeno, dimethylamino, lower alkyl, or lower haloalkyl). The salicylic acid derivatives represented by the general formula (I·II) or salts thereof are useful as active ingredients of disease controllers for agricultural and horticultural use, and disease controllers containing the derivatives or the salts exhibit excellent control activities against diseases.

Description

 Specification

 Salicylic acid derivative, method for producing the same, and agricultural and horticultural disease controlling agent

 Technical field

 The present invention relates to a salicylic acid derivative, a method for producing the same, and an agricultural and horticultural disease control agent containing the salicylic acid derivative as an active ingredient.

 Background art

 [0002] Conventionally, use of a salicylic acid derivative as a fungicide for agricultural and horticultural use has been proposed (Patent Documents 1 and 2).

 [0003] Further, use of 2,6-dichloro-4-pyridinemethanol and its benzoate derivative as an agricultural chemical has been proposed (Patent Document 3).

 Patent Document 1: JP-A-8-291110

 Patent Document 2: JP-A-10-29961

 Patent Document 3: JP-A-11-171864

 Disclosure of the invention

 Problems to be solved by the invention

 [0004] In view of the above circumstances, the present inventors have developed agricultural and horticultural diseases which exhibit low toxicity to humans and animals, high safety in handling, and excellent control effects on a wide range of plant diseases. In order to develop a control agent, salicylic acid derivatives of the following formulas (I and II) and their salts were synthesized and their disease control effects were examined. Accordingly, an object of the present invention is to provide an agricultural and horticultural disease control agent comprising a salicylic acid derivative, a method for producing the same, and a salicylic acid derivative or a salt thereof as an active ingredient.

 Means for solving the problem

 [0005] The inventors of the present invention have conducted intensive studies in order to solve the problem, and as a result, the salicylic acid derivative represented by the formula (Ι · Π) is a novel compound, and is a disease control agent for agricultural and horticultural use. As a result, the present invention has been completed.

[0006] The present invention has been completed based on the above findings, and a first gist of the present invention is an agricultural chemical containing a salicylic acid derivative of the following formula (Ι · Ι) or a salt thereof as an active ingredient. Gardening _{C in} disease control agents

 [0007] [Formula 1]

[0008] In the formula, X represents a lower alkyl group, a lower alkoxy group, a lower haloalkyl group or a halogen atom, and m represents an integer of 0 to 3. When m is 2 or more, X may be the same or different. R ¹ represents a hydrogen atom or a lower alkyl group; R ² represents a hydrogen atom, a hydroxyl group, a halogen atom, a dimethylamino group, a lower alkyl group or a lower haloalkyl group.

[0009] A second gist of the present invention is to react a 2-hydroxybenzoic acid derivative of the following formula (III) with a substituted benzylnolide of the formula (IV), And a method for producing a substituted salicylic acid of the formula (I), characterized in that the ester moiety is hydrolyzed.

[0010] [Formula 2]

[0011] In the formula, X represents a lower alkyl group, a lower alkoxy group, a lower haloalkyl group, or a halogen atom, and m represents an integer of 0 to 3. When m is 2 or more, X may be the same or different. R represents a lower alkyl group. R ² represents a hydrogen atom, a hydroxyl group, a halogen atom, a dimethylamino group, a lower alkyl group or a lower haloalkyl group, and Y represents a halogen atom.

 A third aspect of the present invention resides in a salicylic acid derivative of the above formula (Ι · Ι) or a salt thereof.

 The invention's effect

According to the present invention, the salicylic acid derivative of the formula (Ι · Π) and a salt thereof are used for controlling agricultural and horticultural diseases. The agricultural and horticultural disease control agent has an excellent disease control effect.

 BEST MODE FOR CARRYING OUT THE INVENTION

Hereinafter, the present invention will be described in detail. Among the definitions of the substituents of the salicylic acid derivative (Ι · Π) of the present invention (hereinafter sometimes abbreviated as “the compound of the present invention”), the substituents shown in the general concept include the following preferred substituents Is included. Examples of the lower alkyl group for X include a methyl group, an ethyl group, a 1-methylethyl group, a 1,1-dimethylethyl group and a propyl group.Examples of the lower alkoxy group include methoxy, ethoxy, 1-methylethyloxy, 1 , 1 dimethylethyloxy and propyloxy; a halogen atom includes a fluorine atom, a chlorine atom, a bromine atom and an iodine atom; and a lower haloalkyl group includes a trifluoromethyl group. Preferred integers m are 0 and 1. Examples of the lower alkyl group for R ¹ and R include a methyl group, an ethyl group, and a 1-methylethyl group. The halogen atom for R ² includes a fluorine atom, a chlorine atom, a bromine atom and an iodine atom, and the lower alkyl group includes a methyl group, an ethyl group, a 1-methylethyl group, a propyl group and a 2-methylpropyl group. The lower haloalkyl group includes a trifluoromethyl group. Examples of the salt of the salicylic acid derivative (Ι · Π) include salts containing sodium, potassium, copper, or 1-methylethylamine. In the definition of the substituent, a lower alkyl group, a lower alkoxy group, or a lower haloalkyl group is preferably a group having a carbon chain of 114 carbon atoms including the exemplified groups. Further, a lower haloalkyl group refers to a group in which one or more hydrogen atoms of a lower alkyl group are substituted with a halogen atom, preferably a fluorine atom.

 Next, specific examples of the salicylic acid derivative (Ι · Π) are shown in Table 1.

[Table 1] H HO HS— I

 io-g H H I-I

 H ¾D ½-II

 D-S HO ss-ii

 D

H IS -II

 D S Ό 02— II

 1 s 9W 61 -II

 ng-g g H 8T-II

 ¾-i-g H ΐ-ΙΙ

 ^ a-s H 91 -II

 -s H ^ 3 ST— II s I I G II

 H ει-π

 -ig-g H St— π

 IDS H 3W ΐΙ-ΙΙ

 d-9 H 01 -II

 H ng-i 3W 6— II

 H Yu d-u 8— π

 H Ζ-ΙΙ

 H 9-1 II

 H S-II

 H 13 ー π

 H Λ ε— π

 H HO 2-ΙΙ

 H H 9 G II

 rax ΐ ¾

lZLZl0 / t00Zdi / ∑3d 0n 0 / SOOZ OAV [0017] In the table, 5-C1 in the compound () -ll) represents a chlorine atom bonded to the 5-position. 3,5-C1 in the compound (Π-20) indicates that a chlorine atom is bonded to the 3- and 5-positions. You

 2

 That is, the number before the no and the ifen (-) indicates the bonding position, and the number after the hyphen (-) indicates the number of substituents and the number of substituents when there are two or more substituents of the same type. H in the compound (II 1) indicates that it is unsubstituted. This rule is also used for the substituent Xm.

[0018] Examples of the diluent used in the production method of the present invention include the following. Water, organic acids such as formic acid, acetic acid, and propionic acid; hydrocarbons such as benzene, toluene, xylene, petroleum ether, pentane, hexane, and heptane; and halogenated hydrocarbons such as methylene chloride, chloroform, and carbon tetrachloride. Alcohols such as methanol, ethanol, isopropanol and t-butanol, ethers such as getyl ether, dimethoxyethane, diisopropyl ether, tetrahydrofuran, diglyme and dioxane, carbon disulfide, acetonitrile, acetone, Ethyl acetate, acetic anhydride, pyridine, dimethylformamide, dimethylacetamide, 1-methyl-2-pyrrolidinone, dimethylsulfoxide, hexamethylphosphoric amide and the like.

[0019] Examples of the base include the following. Alkali metal carbonates such as sodium carbonate, sodium bicarbonate, potassium carbonate and potassium bicarbonate; alkaline earth metal carbonates such as calcium carbonate and barium carbonate; alkalis such as sodium acetate, potassium acetate and sodium propionate Metal carboxylates, alkali metal hydroxides such as sodium hydroxide and potassium hydroxide, alkaline earth metal oxides such as magnesium oxide and calcium oxide, lithium, sodium, potassium, etc. Alkali earth metals such as magnesium, magnesium, etc., alkali metal alkoxides such as sodium methoxide, sodium ethoxide, potassium t-butoxide, alkali metal hydrides such as sodium hydride, potassium hydride, methyllithium, ethyllithium, etc. n-Butyllithium, ferric Organic metal compounds of alkali metals, such as organic compounds, organic Grignard reagents such as methyl magnesium iodide, ethyl magnesium bromide, n-butyl magnesium bromide, organic metal compounds of alkali metals, and Grignard reagents and copper (I) salts Organic copper compounds, alkali metal amides such as lithium diisopropyl pyramide, ammonia water, benzyltrimethylammonium hydroxide, ammonium hydroxides such as tetramethylammonium hydroxide, methylamamine, etc. Organic amines such as ethylamine, n-propylamine, benzylamine, ethanolamine, dimethylamine, benzylmethylamine, dibenzylamine, triethylamine, triethanolamine and pyridine.

 [0020] The salt of the first transition element used in the production of the metal complex salt of the salicylic acid derivative (Ι · Π) includes three types of salts of acetate, hydrochloride, nitrate, and sulfate (hydrochloride, nitrate or sulfate). It is advantageous to use an alkali metal acetate, carbonate or hydroxide at the same time). Examples of the acid include inorganic acids such as hydrochloric acid, hydrobromic acid, hydroiodic acid, perchloric acid, nitric acid, and sulfuric acid, and organic acids such as formic acid, acetic acid, butyric acid, and Ρ-toluenesulfonic acid. .

 [0021] Salicylic acid ester (II), which is a precursor of substituted salicylic acid (I), is prepared by reacting 2-hydroxybenzoic acid derivative (ΠΙ) with 2,6-dichloro-4-halogenomethyl pyridine (IV) in the presence of a base. It can be advantageously produced in diluents. In order to carry out the production method of the present invention, for example, 2-hydroxybenzoic acid derivative (ΠΙ) is dissolved in the above-mentioned diluent, and if necessary, in the presence of the above-mentioned base, 2, 6 —Dichloro-4 halogenomethyl pyridine (IV) is usually 0.5-1.5 equivalents, or reverse diluent 2,6-dichloro-4 halogenomethyl pyridine (IV) dissolved in diluent. It is preferable to add 2-hydroxybenzoic acid derivative (III) and a base to react with each other. As the reaction temperature at this time, any temperature up to the freezing point and boiling point of the diluent as a solvent can be applied, but in practice, the reaction is preferably performed at a temperature in the range of 0 to 100 ° C. The reaction time is usually in the range of 110 hours, and it is desirable to carry out the reaction with stirring. After the completion of the above reaction, the reaction mixture obtained by the reaction was cooled, extracted with an organic solvent such as ethyl acetate, chloroform, and benzene to separate an organic layer, and then the organic layer was washed with water. After drying, the solvent is distilled off under reduced pressure, and the obtained residue is purified, whereby salicylate (Π) can be obtained. The purification treatment can be performed by recrystallization or silica gel column chromatography.

[0022] The hydrolysis of the ester portion of salicylate (II) can be performed as follows. The salicylic acid ester (II) and the alkali metal hydroxide are added to a hydrous alcohol, and the mixture is usually refluxed at 20 to 100 ° C or 20 ° C at the reflux point of the solvent for usually 120 hours. After the reaction, the reaction mixture was acidified, and the precipitate was collected by filtration or the solvent was distilled off. Stir well and filter off insolubles. Then, the filtrate is recrystallized to obtain the substituted salicylic acid (I).

 [0023] Since the substituted salicylic acid (I) thus obtained has an acidic proton, it can form a salt in which a hydrogen atom is substituted with an appropriate cation. These salts are generally metal salts, especially alkali metal salts, alkaline earth metal salts or complex salts with first transition elements, including copper, or, in some cases, ammonium salts, alkylated ammonium salts or organic salts. And preferably can be prepared in a solvent such as, for example, water, methanol or acetone, usually at a temperature of 20-100 ° C.

Next, the usefulness of the salicylic acid derivative of the formula (II) according to the present invention as an active ingredient of an agricultural and horticultural disease controlling agent will be described. The salicylic acid derivative (Ι · Π) of the present invention has an effect of controlling a wide range of plant diseases shown below. For example, rice blast (Pyriculana oryzae), rice sorghum (Cochiiooolus miyaoeanus), rice seedling disease (Gioberella lujiKuroi), rice small black tooth nucleus; ¾ | ¾ (Helminthosponum sigmoideum), Disease fungi (Rhizoctonia solani), gray mold disease that causes various crops (Botrytis cinerea), sclerotium sclerotium (Sclerotinia scierotiorum), sclerophyte (Fusanum oxysporum f.sp. niveum), yuuri vine ( Cucumennum, Fusarium oxysporum f.sp. cucumennum, Colletotrichum lagenarium, Anthe brown leaf spot (Cercospora beticola), Soybean purple spot (Cercospora kikuchii), Peach leaf spot (Sclerotinia cinerea), Apple spot spot ίhei fungus (Alternaria alternata (mali)), Nan black spotted fungus (Alternaria alternata (kikuchiana)), bud ^, no rot! ul (ulomerella cingulata), = yuribe and 3 (Pseudoperonosora cubensis), tomato plague (Phytophthra) infestans), cucumber gray plague (Phytophthora capsici), Rice seedling blight fungus (Pythium aphanidermatum).

[0025] In order to apply the salicylic acid derivative (農 · Π) as the agricultural and horticultural disease controlling agent as described above, the compound can be used as it is, but usually, together with a formulation auxiliary, a powder, a wettable powder, and a granule are used. Formulations and emulsions are used in various forms. At this time, the preparation usually contains 0.1 to 95% by weight, preferably 0.5 to 90% by weight, more preferably 2 to 70% by weight of one or more salicylic acid derivatives (Ι · Π). Formulated so that Examples of carriers, diluents, and surfactants used as formulation aids include talc, kaolin, and vein as solid carriers. Liquid, diluents such as water, xylene, toluene, cyclobenzene, cyclohexane, cyclohexanone, dimethylsulfoxide, dimethylformamide, alcohols, etc. Surfactants that can be properly used depending on their effects include polyoxyethylene alkylaryl ether, polyoxyethylene sorbitan monolaurate, etc., and lignin sulfonate as a dispersant. , Dibutylnaphthalenesulfonate and the like, and wetting agents include alkylsulfonate, alkylphenolsulfonate and the like. Some of the above preparations are used as is, and others are diluted to a certain concentration with a diluent such as water.

. The concentration of the compound of the present invention when used after dilution is preferably in the range of 0.001 to 1.0%. The amount of the compound of the present invention is usually 20 to 5000 g, preferably 50 to 100 g per lha of agricultural and horticultural land such as fields, fields, orchards and greenhouses. Since the concentration and amount of use vary depending on the dosage form, the time of use, the method of use, the place of use, the target crop, and the like, it is of course possible to increase or decrease the amount without being limited to the above range. Furthermore, the compounds of the present invention can be used in combination with other active ingredients, for example, fungicides, insecticides, acaricides, herbicides. Incidentally, since the present conjugate contains a carboxylic acid, it can be used in the form of inorganic salts, organic salts or metal complex salts.

 Example

 Hereinafter, the present invention will be described in more detail with reference to Production Examples, Formulation Examples, and Test Examples, but the present invention is not limited to the following Production Examples as long as the gist is not exceeded. The NMR ^ vector was measured using TMS as an internal standard, and indicated by the following symbols or a combination of these symbols. s: double line, d: double line, t: triple line, q: quadruple line, m: multiple line, b: broad line, dd: double double line, qq: quadruple line

 Production Example 1:

 <Preparation of 6-chloro-2— (2,6-dichloro-4pyridylmethoxy) benzoic acid methyl ester (Danizo Compound No. Π-4)>

0.93 g of methyl salicylic acid methyl ester was dissolved in 50 ml of acetone, and 1.35 g of potassium carbonate and 1. lg of 4-chloromethyl-2,6-dichloromouth pyridine were added, followed by heating under reflux for 8 hours. After completion of the reaction, water was poured into the reaction solution, and extraction was performed with ethyl acetate. Organic layer is saturated with water After successive washing with brine, drying over anhydrous sodium sulfate, the solvent was distilled off, and the resulting residue was subjected to column chromatography (CO-gel C300 hexane / ethyl acetate = 8Z1), 1.3 g of the target compound was obtained. Table 2 shows the physical properties of this compound.

[Table 2]

(1) Melting point: 141-142 ° C

 (2) IR (NaCl method, v, cm: 3472, 1740, 1592, 1480, 1276, 1066

(3) NMR (CDC13, δ, ppm): 3.99 (3H, s), 5.09 (2H, s) ₎ 6.78 (lH, d, J = 8.1Hz),

 7.09 (lH, d, J = 8.1Hz), 7.26 to 7.51 (3H, m)

Production Example 2:

 <Production of 2- (2,6-dichloro-4-pyridylmethoxy) -5-chlorobenzoic acid methyl ester (I-Danigo Compound No. Π-11)>

 0.186 g of methyl 5-salicylic acid methyl ester was dissolved in 6 ml of anhydrous acetone, 1.1 g of lithium carbonate and 0.241 g of 4-bromomethyl-2,6-dichloropyridine were added, and the mixture was heated under reflux for 16 hours. After the completion of the reaction, water was added to the reaction solution, and extracted with ethyl acetate. The organic layer was washed sequentially with saturated saline and water, dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 0.294 g of the desired compound. Table 3 shows the physical properties of this compound.

[Table 3]

(1) Melting point: 140-142 ° C

 (2) IR (NaCl method, v, cm-: 2908,1700,1606, 1456,1280,1074

(3) NMR (CDC13, δ, ppm): 4.00 (3H, s), 5.12 (2H, s), 6.8 to 7.6 (5H, m) ₁ 7.53 (2H, bs)

Production Example 3:

 <Production of 2- (2,6-dichloro-4-pyridylmethoxy) -6-hydroxybenzoic acid (I-drug No. 1-2)>

Under a nitrogen stream, 0.4 g of 60% oily sodium hydride was washed with anhydrous hexane, and then suspended in 100 ml of anhydrous dimethylformamide. Under ice-cooling and stirring, 1.68 g of 2,6-dihydroxybenzoic acid methinolate was added, and a solution prepared by dissolving 2.65 g of 4-bromomethinolee 2,6-dichloropyridine in 30 ml of dimethylformamide was added dropwise. After 1 hour, gradually increase the reaction temperature The reaction was performed for 6 hours while maintaining the temperature at about 30 ° C. After completion of the reaction, water was added to the reaction station, and extraction was performed using ethyl acetate. The organic layer was washed successively with water and saturated saline, and then dried over anhydrous sodium sulfate. After evaporating the solvent, the obtained residue was purified by silica gel column chromatography to obtain 2.3 g of a salicylic acid ester (Danigari Compound No. III-3) which is a methyl ester of the target compound. Table 4 shows the physical properties of this compound.

[0032] [Table 4]

(丄) Melting point: 136 ~ 137 ° C

 (2) IR (NaCl method, v, cm-R: 1660,1592,1464,1260,1104

 (3) NMR (CDC13, δ, ppm): 4.07 (3H, s), 5.17 (2H, s), 6.48 (lH, d, J = 8.0 Hz),

6.67 (lH, d ₎ 8.0Hz), 7.37 iH, t, J = 8.0Hz), 7.53 (2H, bs), 11.2 (lH, bs)

[0033] 0.25 g of the obtained salicylate was dissolved in 30 ml of ethanol, 20 ml of water and 0.5 g of sodium hydroxide were added, and the mixture was heated at 50 ° C for 3 hours. After completion of the reaction, the reaction solution was neutralized with dilute hydrochloric acid, and then subjected to an extraction treatment using black form. The organic layer was washed sequentially with water and saturated saline, and then dried over anhydrous sodium sulfate. The solvent was distilled off and recrystallized from chloroform-form methanol to obtain 0.15 g of the desired compound. Table 5 shows the physical properties of this compound.

 [0034] [Table 5]

(1) Melting point: 235-236 ° C

 (2) IR (NaCl method,, cm-: 1654 '1620, 1604, 1464, 1244, 1108

 (3) NMR (CDC13, δ, ppm): 5.19 (2H, s), 6.53 (lH, d, J = 8.0 Hz), 6.70 (lH, d, J = 8.0 Hz),

 7.42 (lH, t, J = 8.0Hz), 7.5 (2H, bs), 11.2 (lH, bs)

[0035] The compounds shown in Tables 6 to 7 below were synthesized by operations according to Production Examples 13 to 13 described above. The melting points and NMR data of these compounds are shown in Tables 6-7.

[Table 6]

ZY 0..CZ0 / S00Z OAV ぐ

 ■ z m [6εοο]

<Skill>

izLzio / toozdr / Ud 0..CZ0 / S00Z OAV 50 parts by weight of the compound of the present invention (I-Danied Compound No. III-3), 5 parts by weight of lignesulfonate, 3 parts by weight of alkylsulfonate and 42 parts by weight of diatomaceous earth were mixed by pulverization to obtain a wettable powder. Use it after dilution.

[0040] Formulation Example 3:

 <Granules>

 5 parts by weight of the compound of the present invention (I-Danied Compound No. Π-7), 43 parts by weight of benite, 45 parts by weight of clay and 7 parts by weight of lignesulfonate are uniformly mixed, and the mixture is kneaded by kneading with water. It is processed into granules by a dispensing granulator and dried to obtain granules.

Formulation Example 4:

 <Emulsion>

 20 parts by weight of the compound of the present invention (I-Ridant No. Π-10), 10 parts by weight of polyoxyethylene alkyl aryl ether, 3 parts by weight of polyoxyethylene sorbitan monolaurate and 67 parts by weight of xylene are uniformly mixed and dissolved. To obtain an emulsion.

 Test example 1:

 <Rice blast control effect test (water application)>

 Transplant rice (variety: Koshihikari) at the 3 leaf stage into a 1/1 OoWa Wagner pot filled with paddy soil, and after 20 to 35 days, the granules adjusted according to Formulation Example 3 have a predetermined concentration (500 g / 10a) Was applied to the water surface in the same manner. 10 to 20 days after the chemical treatment, a spore suspension of the rice blast fungus formed on the rice disease was sprayed and inoculated, and kept under high humidity in a vinyl tunnel in a glass greenhouse. After 10-20 days, the inoculation power was examined arbitrarily for the diseased area rate (%), and the disease incidence was investigated for all seedlings per test plot according to the survey criteria shown in Table 8 below (Chinese agricultural test blast criterion). The control value (%) was calculated from the average disease rate per pot using the following formula: control value = (1-disease rate in treated area Z disease rate in untreated area) x 100. Table 9 shows the results.

[Table 8] Disease severity Disease area rate (%)

 0 0

 More than 10 and less than 0.5

2 0.5 or more and less than 1

3 1 or more and less than 2

 4 2 or more and less than 5

 5 5 or more and less than 10

6 10 or more and less than 25

7 25 or more and less than 50

8 50 or more and less than 80

9 80 or more and less than 100

10 Withering

[Table 9]

[0045] Test example 2: <Effect of controlling wheat powdery mildew (foliage application)>

 Using a square pot (1.5 cm X 2. Ocm), wheat (cultivar: Norin 61) cultivated in a greenhouse at the tillering stage was mixed with a wettable powder prepared according to Formulation Example 2 at a specified concentration ( The suspension was diluted with water at 125 g / ha) and sprayed at a rate of 100 L / ha. 10 to 20 days after drug treatment, spores of wheat powdery mildew were sprinkled and inoculated. Thereafter, the disease was caused in a glass greenhouse. 10 to 20 days after the inoculation, the disease area rate (%) is examined arbitrarily. Based on the survey criteria in Table 10 below, the formula is calculated from the average disease rate per pot: control value = (1-treatment area disease rate Z The control value (%) was calculated by X100. Table 11 shows the results.

[Table 10]

[Table 11]

■ f danger compound number ^ ^ compound number

II-I 1 65 85

II-II 2 90 11-15 85

II-I 3 85 11— 16 75

 (D 11— 17 90

II ο o 11—18

ίυ o

II-I 7 80 11-20 75 c

II 1 8 75 65

II 9 60 11-22 90

II 10 75 11-23 70

 95 95

II- 12 80 1-1 75

11-13 85 1-2 inch 70

Claims

Claims [1] An agricultural and horticultural disease controlling agent comprising a salicylic acid derivative of the following formula (ι · π) or a salt thereof as an active ingredient.

 [Chemical 1]

(In the formula, X represents a lower alkyl group, a lower alkoxy group, a lower haloalkyl group or a halogen atom, and m represents an integer of 0 to 3. When m is 2 or more, X is the same or different. R ¹ represents a hydrogen atom or a lower alkyl group, and R ² represents a hydrogen atom, a hydroxyl group, a halogen atom, a dimethylamino group, a lower alkyl group or a lower haloalkyl group.)

 [2] A method for producing a salicylic acid ester of the formula (II), which comprises reacting a 2-hydroxybenzoic acid derivative of the following formula (III) with a substituted benzylno or ride of the formula (IV).

[Chemical 2]

(In the formula, X represents a lower alkyl group, a lower alkoxy group, a lower haloalkyl group or a halogen atom, and m represents an integer of 0 to 3. When m is 2 or more, X is the same or different. R represents a lower alkyl group, R ² represents a hydrogen atom, a hydroxyl group, a halogen atom, a dimethylamino group, a lower alkyl group or a lower haloalkyl group, and Y represents a halogen atom.)

 [3] A salicylic acid derivative represented by the following formula (Ι · Π) or a salt thereof.

 [Formula 3]

(In the formula, X is a lower alkyl group, a lower alkoxy group, a lower haloalkyl group or a halogeno group. And m represents an integer of 0 to 3. When m is 2 or more, X may be the same or different. R ¹ represents a hydrogen atom or a lower alkyl group; R ² represents a hydrogen atom, a hydroxyl group, a halogen atom, a dimethylamino group, a lower alkyl group or a lower haloalkyl group. )