WO2002062759A1

WO2002062759A1 - Iminooxymethylpyridine compound and agricultural or horticultural bactericide

Info

Publication number: WO2002062759A1
Application number: PCT/JP2002/000792
Authority: WO
Inventors: Shunichiro Fukumoto; Atsushi Shibayama; Masaru Shibata; Norihisa Yonekura; Makiichi Takagaki; Ichiro Miura; Kouzou Nagayama
Original assignee: Kumiai Chemical Industry Co., Ltd.; Ihara Chemical Industry Co., Ltd.
Priority date: 2001-02-02
Filing date: 2002-01-31
Publication date: 2002-08-15
Also published as: JP4246996B2; JPWO2002062759A1

Abstract

A novel iminooxymethylpyridine compound derivative having the following general formula [I]; and an agricultural or horticultural bactericide containing the derivative as the active ingredient. [I] In the formula, X represents halogeno, C1-6 alkyl, C1-6 alkoxy, C1-6 haloalkyl, or C1-6 haloalkoxy; Y represents halogeno, C1-6 alkyl, or C1-6 alkoxy; l is 0, 1/2, or 1; m and n each independently is an integer of 0 to 4; R1 represents C¿1-6? alkyl; R?2¿ represents hydrogen, C¿1-6? alkyl, or C1-6 haloalkyl; and H-A represents an acid substance.

Description

Technical field Ginseng compounds and fungicides for agricultural and horticultural use

The present invention relates to an agricultural and horticultural fungicide containing a novel iminooxymethylpyridine compound as an active ingredient. Background art

Although many iminooxymethylpyridine compounds have been reported, it is not known that the iminooxymethylpyridine compound having a benzylcarbamate group of the compound of the present invention has an excellent bactericidal action.

An object of the present invention is to provide a novel iminooxymethylbiridinium compound and a fungicide for agricultural and horticultural use containing the same as an active ingredient. Disclosure of the invention

The present inventors have conducted intensive studies to create a novel fungicide for agricultural and horticultural use. As a result, the iminooxymethylpyridine compound of the present invention (hereinafter referred to as the compound of the present invention) is a novel compound not described in the literature. The present invention was also found to exhibit a remarkable effect as a fungicide for agricultural and horticultural use, and completed the present invention. That is, the present invention provides the inventions described in the following (1) and (2).

(1) General formula [I]

(Wherein, X is a halogen atom, C c ₆ alkyl group, cc _fi alkoxy group of 1 to ₍₆ represents Haroarukiru group or (3 _1-0 ₆ Haroarukokishi group, Y halo Gen atom, (^ to ₆ alkyl group or (^ to (: ₆ alkoxy group, 1 represents 0, 1 Z 2 or 1; m and n each independently represents 0 or an integer of 1 to 4; R ¹ represents a Ci-C ₆ alkyl group, R ² represents a hydrogen atom, (^ -〇 ₆ alkyl group or (:! ~., An alkyl group, H—A represents an acidic substance). And (2) a fungicide for agricultural and horticultural use containing these as an active ingredient.

The symbols and terms described in this specification will be described.

A halogen atom is a fluorine atom, a chlorine atom, a bromine atom or an iodine atom. The notation such as (^ to ( _{1 ())} indicates that the number of carbon atoms of the substituent following this is 1 to 10 in this case.

Ct Ce alkyl group means a linear or branched alkyl group, for example, methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, Examples include groups such as n-pentyl, iso-pentyl, neopentyl, n-hexyl, 1,1-dimethylpropyl, and 1,1-dimethylbutyl.

Ji, ~. ^ The alkyl group indicates a straight or branched chain alkyl group, and said -C ₆ alkyl group, heptyl to n-, n- old corruptible or n- dodecyl groups.

The C! Ce alkoxy group means an alkyloxy group in which the alkyl moiety has the above-mentioned meaning, for example, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, n — Pentyloxy, isopentyloxy or n-hexyloxy.

(^-., Mouth alkyl group means a linear or branched alkyl group substituted by a halogen atom, such as fluoromethyl, chloromethyl, difluoromethyl, dichloromethyl, trifluoromethyl or pentafluoroethyl. Groups.

C! Cs haloalkoxy group means that the haloalkyl moiety has the meaning described above. A haloalkyloxy group, for example, a group such as fluoromethoxy, difluoromethoxy, trifluoromethoxy, or penfluoromethoxy.

The naphthyl group includes a 1-naphthyl group or a 2-naphthyl group.

The acidic substance is, for example, an inorganic acid such as sulfuric acid, nitric acid, hydrogen chloride or hydrogen bromide; a naphthalene sulfonic acid such as 1-naphthylene sulfonic acid or 2-naphthylene sulfonic acid; methanesulfonic acid, propanesulfonic acid, Pentansuru acid or the like hexane sulfonic acid (^ ~ Arukirusu sulfonic acid;. C i~C ₆ Bruno, mouth alkyl carboxylic acids such as Torifuruoro acetate; oxalic acid; malonic C j C s alkyl carboxylic acids such as acetic acid Or succinic acid

Alkyl dicarponic acid; C j -C ₁₆ alkyl benzene sulfonic acid such as benzene sulfonic acid, paratoluene sulfonic acid and n-dodecyl benzene sulfonic acid.

Next, specific examples of the compound of the present invention represented by the general formula [I] are described in Tables 1 to 5. However, the compound of the present invention is not limited to these compounds. The compound numbers will be referred to in the following description.

Some of the compounds of the present invention represented by the general formula [I] have one double bond in the molecule, and such compounds include EZZ isomer mixtures. Pure individual E-forms, Z-forms and mixtures thereof are also included in the compounds of the present invention.

A typical method for producing the iminooxymethylpyridine compound represented by the general formula [Ia] or [Ib], which is the compound of the present invention, is illustrated below. Note that the novel compound represented by the general formula [I] has a C = N double bond and may be produced as a mixture of E / Z isomers during production. This isomer mixture can be isolated into individual components by a purification method such as crystallization or column chromatography. Individual isomers as well as mixtures thereof are encompassed by the present invention.

Manufacturing method>

Process 1

III] [Ia]

(In the formula, RR ² , X, Y, HA, m, and n each have the same meaning as described above, and L represents a defensive group and represents a halogen atom or a sulfonate such as paratoluenesulfonyloxy.)

The compound [11] and the compound [III] are reacted in the presence of a base to produce the present compound [I-a] (step 1), and the compound [I-a] of the present invention is further converted to an acidic substance [ IV] (Step 2), the present compound [Ib] can be produced. Compound [III] can also be used as a pyridinium salt.

The amount of the starting compound used in step 1 of this reaction may be appropriately selected from the range of 1 to 50 equivalents of compound [III] to compound [II], preferably 1 to 10 equivalents. Is equivalent. Inert solvents that can be used in this production method include alcohols such as methanol, ethanol, propanol or isopropanol, getyl ether, diisopropyl ether, and tetrahydrofuran. Orchid, dioxane, dimethoxetane or diethylene glycol.

Use ethers such as ethers, aromatic hydrocarbons such as benzene, cyclobenzene, nitrobenzene or toluene, aprotic polar solvents such as dimethyl sulfoxide, N, N-dimethylformamide or sulfolane, water, etc. These inert solvents can be used alone or as a mixture.

Examples of the base used in step 1 of this reaction include alkali metal hydrides such as sodium hydride, alkali metal alcoholates such as tert-butoxycalidium, and inorganic salts such as sodium carbonate and potassium carbonate. The amount of the base used may be appropriately selected from the range of 1 to 50 equivalents relative to compound [II], and is preferably 1 to 10 equivalents.

The reaction temperature is from −10 ° C. to the boiling point of the inert solvent used, and preferably from 0 ° C. to the boiling point of the inert solvent used.

The reaction time is not fixed depending on the reaction temperature, the reaction amount and the like, but may be generally selected from the range of 1 hour to 72 hours.

After completion of the reaction, the compound [Ia] is isolated from the reaction system by a conventional method, and if necessary, purified by column chromatography or recrystallization.

The amount of the acidic substance [IV] used in Step 2 of this reaction may be appropriately selected from the range of 1 to 100 equivalents of the acidic substance [IV] to the compound [I-a], and is preferably 30 to 70 equivalents.

The acidic substance [IV] used in step 2 is, for example, a mineral acid such as hydrochloric acid, sulfuric acid, nitric acid, or hydrobromic acid; a hydrogen halide such as hydrogen chloride or hydrogen bromide; 1-naphthalenesulfonic acid or 2 —Naphthalenesulfonic acids such as naphthylenesulfonic acid; alkylsulfonic acids such as methanesulfonic acid, propanesulfonic acid, pentanesulfonic acid or hexanesulfonic acid; alkylcarboxylic acids such as acetic acid; haloalkylcarboxylic acids such as trifluoroacetic acid; Oxalic acid; alkyldicarboxylic acids such as malonic acid or succinic acid; and alkylbenzenesulfonic acids such as benzenesulfonic acid, paratoluenesulfonic acid or n-dodecylbenzenesulfonic acid.

In step 2, a solvent can be used in some cases. As the solvent, Alcohols such as methanol, ethanol, propanol or isopropanol, ethers such as dimethyl ether, diisopropyl ether, tetrahydrofuran, dioxane, dimethoxetane, or diethylene darichol dimethyl ether, benzene, Aromatic hydrocarbons such as benzene, nitrobenzene or toluene, water and the like can be used, and these inert solvents can be used alone or as a mixture.

The reaction temperature is from 11 ° C. to the boiling point of the inert solvent used, preferably from 0 to the boiling point of the inert solvent used.

The reaction time is not fixed depending on the reaction temperature, the reaction amount and the like, but may be generally selected from the range of 1 to 48 hours.

The compound [II], which is an intermediate of the compound [I] of the present invention, can be produced by, for example, the following known methods, but is not limited to those shown here.

(Wherein, RR ² , X and n each have the same meaning as described above, and L ′ is a leaving group and represents a halogen atom.)

Compound [VI] can be produced by halogenating compound [V] with a halogenating agent such as N-bromosuccinimide, N-chlorosuccinimide or trichloroisocyanuric acid. (For example, see the 4th edition Experimental Chemistry Course, Vol. 19, pp. 4 16-482 (edited by The Chemical Society of Japan)) (Process A-1). Further, the intermediate [VIII] can be produced by reacting the compound [VI] with an alkali metal cyanate such as potassium cyanate or sodium cyanate and the compound [VII] in an inert solvent (for example, Japan Chemical Journal, Vol. 87, No. 5, pp. 486 (1966)) (Process A-2).

Further, the intermediate [II] can be produced by reacting the compound [VIII] with the compound NH ₂ OH (for example, Experimental Chemistry Course, 4th edition, Vol. 20, pp. 349-355) (See Chemical Society of Japan)) (Process A-3). The starting compound NH ₂ 0H to be used in the present process is hydrochloric acid, may form and the sulfate.

The compound [II-a] which is an intermediate of the compound [I] of the present invention can also be produced, for example, by the following known method.

[Il-a]

(Wherein, RR ² and L ′ each have the same meaning as described above, and X ¹ , X ² , X ³ and X ⁴ each represent a hydrogen atom, a halogen atom, a C! CS alkyl group, a C! -C ₆ alkoxy group , C, ~ C ₆ haloalkyl group or a C, ~ C ₆ haloalkoxy group Represents )

(Process B-1)

Intermediate [X] can be produced by reacting compound [IX] with an alkali metal cyanate and compound [VII] in an inert solvent (for example, Nippon Kagaku Magazine, Vol. 87, No. 5, p. 486 (1966)).

(Process B-2)

The intermediate [XI] can be produced by nitrating the compound [X] with nitric acid, acetyl nitrate or sodium nitrate. (For example, see the 4th edition Experimental Chemistry Course, Vol. 20, pp. 394-399 (edited by The Chemical Society of Japan)).

(Process B-3)

Intermediate [XII] can be produced by reducing compound [XI] by a conventional method (for example, Experimental Chemistry Course, 4th Edition, Vol. 26, pp. 159-266 (edited by The Chemical Society of Japan) ))).

(Process B-4)

Compound [XII] is diazotized with sodium nitrite in the presence of hydrochloric acid, and then is reacted with compound [XIII] in the presence of sodium acetate and copper sulfate to give intermediate [II-a]. It can be manufactured (see, for example, Organic Syntheses, Vol. 5, p. 139 (1973)).

The agricultural / horticultural fungicide of the present invention comprises an iminooxymethyl pyridine compound represented by the general formula [I] as an active ingredient. When the compound of the present invention is used as a fungicide for agricultural and horticultural use, the active ingredient can be used in an appropriate dosage form according to the purpose. Normally, the active ingredient is diluted with an inert liquid or solid carrier, and if necessary, a surfactant and the like can be added to the active ingredient to be used in the form of powders, wettable powders, emulsions, granules and the like. The compounding ratio of the active ingredient is appropriately selected according to need, but 0.1 to 20% (weight) for powders and granules, and 5 to 80% for emulsions and wettable powders. (Weight) is appropriate.

Suitable carriers include, for example, talc, bentonite, clay, kaolin, Examples include solid carriers such as diatomaceous earth, white carbon, vermiculite, slaked lime, silica sand, ammonium sulfate, and urine, and liquid carriers such as isopropyl alcohol, xylene, cyclohexanone, and methylnaphthalene. Examples of the surfactants and dispersants include dinaphthyl methanesulfonate, alcohol sulfate, alkylaryl sulfonate, lignin sulfonate, polyoxyethylene glycol ether, and polyoxyethylene alkyl ether. And polyoxyethylene sorbitan monoalkylate. Examples of the auxiliary include lipoxymethylcellulose.

The fungicide for agricultural and horticultural use of the present invention can be used by spraying foliage, seed treatment, soil application, water surface application or nursery box application, or the like, after diluting these preparations. These application rates will vary depending on the type of compound used, the target disease, the incidence, the extent of the damage, the environmental conditions, and the dosage form used. For example, when used as such as powders and granules, the active ingredient may be appropriately selected from the range of 0.1 to 5 kg, preferably 1 to L kg per 10 ares. When used in liquid form, such as emulsions and wettable powders, it may be appropriately selected from a range of 0.1 ppm to 10 ppm, preferably 10 ppm to 3 ppm. .

The compounds according to the invention belong to the algal fungi (O omy cetes), the ascomycetes (A sc omy cetes), the basidiomycetes (Basidio my cetes). It can control plant diseases caused by fungi. Next, specific bacterial names are given as non-limiting examples. Pseudoperonospora (Pseudoperonospora) genus, for example, cucumber and bacterium (Pseudoperonosporacuben sis), genus Benyuuria (Venturia), such as apple scab (Venturiainaequa 1 is), Erysiphe (Erysiphe) Wheat powdery mildew (E rysiphegraminis), spicy liurium (Pyricu 1 aria) genus, such as rice blast (Pyriculariaoryzae), potrytis (Botrytis) genus, such as Botrytis cineia, Rhizoctonia (Rh izo ctonia), for example, Rhizoctoniaso 1 ani, Puccinia, for example, wheat rust (Puceiniarecondita), Septoria, for example, wheat Bacterial wilt (Septorianodorum), sclerotinia (Sclerotinia) genus bacteria, for example, Sclerotinia sclerotium (Sclerotiniasclerotiorum)

Further, the compound of the present invention may be mixed with an insecticide, other fungicides, herbicides, plant growth regulators, fertilizers and the like, if necessary.

Next, the production method, formulation method and use of the compound of the present invention will be specifically described with reference to examples.

Abbreviations used in the text have the following meanings.

iH— NMR: proton nuclear magnetic resonance

CDC 1 _3: chloroform one d

TMS: Tetramethylsilane

s: singlet; d: doublet;

t: triplet; Q: quartet;

Quint: Quintet; m: Mill tiplet; br: Prod (broad); dd: Double doublet (Example 1)

N- {2-chloro-1--5- [1- (6-methylpyridine-2-ylmethoxy) iminoethyl] benzyl} Preparation of methyl rubamate (Compound No. 26)

N- [2-chloro-1-amino-5- (benzyl)] force Dissolve 10.0 g of methyl rubamate in 100 ml of N, N-dimethylformamide, and add potassium carbonate 1 8.9 g and 1-3.9 g of 2-chloromethyl-6-methylpyridine hydrochloride were added, and the mixture was heated and stirred at 90 to 100 ° C for 8 hours. After completion of the reaction, the reaction solution was poured into water, extracted with ethyl acetate, and the organic layer was washed with water and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was subjected to silica gel column chromatography (ヮ co-gel C-200, elution solvent: hexane Z-ethyl acetate = 4/1) and purified by N— {2—black mouth—5— [1—

(6-Methylpyridine_2-ylmethoxy) iminoethyl] benzyl] force Production of 8.2 g (melting point 93_96 ° C) of methyl rubamate as pale yellow crystals Production Example 2>

N— {2-chloro-5— [1- (6-methylpyridine-12-ylmethoxy) iminoethyl] benzyl} Production of methyl carpamic acid hydrochloride (Compound No. 1)

Dissolve 2.0 g of methyl N- {2-chloro-5— [1— (6-methylpyridine-12-dimethyl) iminoethyl] benzyl] carbamate in 100 ml of a 10% ethanol solution of hydrogen chloride in hydrogen chloride, The mixture was stirred at room temperature for 48 hours. After completion of the reaction, the solvent was distilled off under reduced pressure, and the obtained residue was washed with 30 ml of a mixed solvent of ethyl acetate / acetone (1/1), and N— {2-chloro-5— [1 -— (6 There was obtained 2.3 g (melting point: 129-131 ° C) of methyl methylcarbamate hydrochloride (1-methylpyridine-2-ylmethoxy) iminoethyl] benzyl) as colorless crystals.

N— {2 —Chloro 1-5 — [1-(6-Methylpyridine 12 -ylmethoxy) iminoethyl] benzyl} Preparation of methyl dodecylbenzenesulfonate carbamate (Compound No. 17)

N— {2-chloro-5— [1- (6-methylpyridine-12-ylmethoxy) iminoethyl] benzyl} Dissolve 1.0 g of methyl carbamate in 2 O ml of chloroform and add 0.8 g of dodecylbenzenesulfonic acid. 6 g was added, and the mixture was stirred at room temperature for 1 hour. The residue obtained by concentrating the reaction mixture under reduced pressure was washed three times with 10 ml of ether, and the supernatant was removed by decantation. The residue obtained is dried under reduced pressure to give N- {2-chloro-5- [1- (6-methylpyridine-12-ylmethoxy) iminoethyl] benzyl} -methyl dodecylbenzenesulfonate 1.7 5 g was obtained as a colorless glass.

_{Ή-NMR: (CDC1 3 /} TMS, δ (ppm))

Next, Production Examples of the synthetic intermediate of the compound of the present invention will be shown as Reference Examples.

N- (2-Chloro-5-acetylpentyl) Production of methyl methyl rubamate 4-Chloro-3-methylacetophenone 25.0 g and trichloroisocyanouric acid 13.9 g Was suspended. A 2,2′-azopisisoptyronitrile catalyst amount was added, and the mixture was heated and stirred at 85 to 90 ° C. for 12 hours. After the completion of the reaction, the mixture was cooled to room temperature, and insolubles were separated by filtration. The filtrate was washed with an aqueous sodium hydroxide solution and water in this order, and the organic layer was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the obtained residue, 12.2 g of potassium cyanate and 14.4 g of methanol were added to N, N-dimethylformamide 150 m 1 at 90 ° C. For 4 hours. After completion of the reaction, water was added to the reaction mixture, extracted with ethyl acetate, and the organic layer was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the obtained residue was purified by silica gel column chromatography (ecogel C1200, elution solvent: hexane / ethyl acetate = 3Z1). The obtained crystals were washed with isopropyl ether to obtain 6.0 g of methyl N- (2-chloro-5-acetylbenzyl) -rubamate as colorless crystals.

_{Ή-NMR: (CDC1 3 /} TMS, δ (ppm))

2.59 (s, 3H); 3.70 (s, 3H); 4.50 (d, 2H); 5.31 (br, 1H); 7.46 (d, 1H); 7.81 (dd, 1H); 7.97 (s, 1H)

Next, the formulation method will be specifically described with reference to typical formulation examples of the agricultural and horticultural fungicide of the present invention. In the following description, “%” indicates weight percentage.

Preparation Example 1> Dust

2% of the compound of the present invention (Compound No. 6), 5% of diatomaceous earth and 93% of clay were uniformly mixed and pulverized to obtain a powder.

<Formulation Example 2> Wettable powder

50% of the compound of the present invention (Compound No. 1), 45% of diatomaceous earth, 2% of sodium dinaphthylmethane disulfonate and 3% of sodium ligninsulfonate were uniformly mixed and pulverized to obtain a wettable powder.

Formulation Example 3> Emulsion An emulsion was prepared by uniformly dissolving 30% of the compound of the present invention (Compound No. 3), 20% of cyclohexanone, 4% of calcium polyphosphate and 35% of methylnaphthylene.

<Formulation Example 4> Granules

5% of the compound of the present invention (Compound No. 10), 2% of sodium salt of lauryl alcohol sulfate ester, 5% of sodium ligninsulfonate, 2% of carboxymethylcellulose and 86% of clay are uniformly mixed and pulverized. The mixture was kneaded by adding 20% water, processed into granules of 14 to 32 mesh using an extrusion granulator, and then dried to obtain granules.

Next, effects of the fungicide for agricultural and horticultural use of the present invention will be specifically described with reference to test examples.

Test example 1> Wheat powdery mildew prevention effect test

Wheat seeds (variety: No. 61 Norin 61) were sown in plastic pots with a diameter of 6 cm each and cultivated in a greenhouse. A wettable powder prepared in accordance with Formulation Example 2 is diluted with water so that the active ingredient concentration is 500 ppm, and the wheat seedling with two leaves developed is diluted with water to obtain 10 ml per pot (3, OOO l Zha a) Sprayed. After air-drying, spores of wheat powdery mildew (Erysiphegramraminis) were inoculated and maintained in a greenhouse. Ten days after the inoculation, the diseased area of the first leaf of the entire pot was examined and evaluated according to the criteria in Table 6. The results are shown in Table 7.

Table 7 Evaluation

A We do not notice the onset

B Affected area <5%

C Affected area 5% or more and less than 10%

D Affected area 10% or more Table 8

Test example 2> Wheat blight prevention effect test

Wheat seeds (variety: Norin No. 61) were sown in 10-cm plastic pots each having a diameter of 6 cm and cultivated in a greenhouse. A wettable powder prepared according to Formulation Example 2 is diluted with water so that the active ingredient concentration is 5 OOP pm, and 10 ml (3, 0 0 0 1 / ha) Sprayed. After air drying, spores of wheat scab fungus (Septorianodorum) were inoculated and maintained in a greenhouse. Ten days after the inoculation, the diseased area of the first leaf in the entire pot was examined and evaluated according to the criteria in Table 9. The results are shown in Table 10.

Table 9 Evaluation

A We do not notice the onset

B Affected area <5%

C Affected area 5% or more and less than 10%

D Affected area 10% or more

Table 1 o

Test example 3> Preventive effect test of cucumber gray mold

Four cucumber seeds (variety: Sagami Hanjiro) were sowed in each of 6 cm diameter plastic pots and cultivated in a greenhouse. A wettable powder prepared according to Formulation Example 2 was added to the seedlings of Cucurbita with cotyledons that developed to 500 ppm of the active ingredient. The solution was diluted with water, and 10 ml per pot (equivalent to 4,001 Zha) was sprayed. After air drying, a paper disc soaked with a spore suspension of Botrytiscinerea was placed on the cotyledon surface of the cucumber, and immediately placed in a greenhouse at 22 ° C. Three days after inoculation, the diseased area of cotyledons in the entire pot was examined and evaluated according to the criteria shown in Table 11. The results are shown in Table 12.

Table 11 Evaluation

A We do not notice the onset

B The affected area is less than 25% of the untreated area

C The affected area is 25% or more and less than 50% of the untreated area

D Affected area is 50% or more of the untreated area

Table 1 2

Industrial applicability

The fungicide for agricultural and horticultural use of the present invention can produce cucumber downy mildew, apple scab, wheat powdery mildew, rice blast, cucumber gray mold, rice sheath blight, wheat leaf rust, without causing phytotoxicity to crops. It has a high control effect against wheat wilt and cucumber rot, and has excellent residual effect and rain resistance. Long lasting. In addition, pyridinium salt compounds have the characteristics of improved permeability and infiltration effect, low toxicity to mammals and seafood, and safe use without polluting the environment. Therefore, it is extremely useful as an agricultural and horticultural fungicide.

Claims

Claims General formula [I]

(In the formula, X represents a halogen atom, a CC ₆ alkyl group, (^-^ alkoxy group, -dialkyl group or di, 'c, a mouth alkoxy group, Y represents a halogen atom, (^-( ₆ alkyl represents a group or Ci～C ₆ alkoxy groups, 1 0, 1/2 or an 1, m and n from each independently 0 or 1 represents an integer of 4, R ¹ is C, -C _R alkyl group the stands, R ² is a hydrogen atom, C, -C _fi alkyl or

An iminooxymethylpyridine compound represented by C (: represents a _6- chain alkyl group, and H—A represents an acidic substance).

2. In the general formula [I], X is a halogen atom or a ^ Ce alkyl group, Y is Ci～C ₆ alkyl or C ^ Ce alkoxy group, imino Noo carboxymethyl pyridine compound according to claim 1 .

3. In the general formula [I], X is a halogen atom or a C! Ce alkyl group, Y is a Ci Cs alkyl group or a C! Cs alkoxy group, and H—A is hydrochloric acid, sulfuric acid, or naphthalenesulfonic acid. ! ~ Ji! An alkyl sulfonic acid C, ~ C _fi alkyl carboxylic acid, C, ~ C ₆ haloalkyl carboxylic acid, oxalic acid,

The iminooxymethyl pyridine compound according to claim 1, which is a CC ₆ alkyl dicarboxylic acid,

4. In the general formula [I], X is a halogen atom or a C ^ Ce alkyl group, Y is (: a wide alkyl group or (: a wide alkoxy group), and H—A is a (^-じ ^ alkylbenzenesulfonic acid). The imino according to claim 1, which is Oxymethylpyridine compound.

5. In the general formula [I], X is a halogen atom or a methyl group, n is 1 or 2, Y is Ci～C ₃ alkyl or Cj～C ₃ alkoxy der Ri, m is 0 or 2. The iminooxymethylpyridine compound according to claim 1, wherein R ¹ is a methyl group, R ² is a methyl group or an ethyl group, and the force is 0, 12 or 1.

6. In the general formula [I], X is a chlorine atom or a methyl group, n is 1 or 2, Y is a methyl group, m is 1, R ¹ is a methyl group, ^{2. The} iminooxymethylpyridine compound according to claim 1, wherein R ² is a methyl group or an ethyl group, and 1 is 0, 1 Z2 or 1.

7-In the general formula [I], X is a halogen atom or a methyl group, n is 1 or 2, Y is a C, C ₃ alkyl group or C _{I to} C ₃ alkoxy group, and m is 0 Or 1; R ¹ is a methyl group; R ² is a methyl group or an ethyl group; 1 is 1; and H_A is a C alkylbenzene sulfonic acid. Methylpyridine compound.

8. In the general formula [I], X is a halogen atom or a methyl group, n is 1 or 2, Y is a!! ₃ alkyl group or ^ Cs alkoxy group, and m is 0 or 1. ^{2. The} iminooxymethylpyridine compound according to claim 1, wherein R ¹ is a methyl group, R ² is a methyl group or an ethyl group, 1 is 1, and HA is dodecylbenzenesulfonic acid. .

9. In the general formula [I], X is a chlorine atom or a methyl group, n is 1 or 2, Y is a methyl group, m is 1, R ¹ is a methyl group, R ^{2. The} iminooxymethylpyridine compound according to claim 1, wherein ² is a methyl group or an ethyl group, 1 is 1, and HA is dodecyl benzenesulfonic acid.

10. A fungicide for agricultural and horticultural use comprising the iminooxymethylpyridine compound according to any one of claims 1 to 9 as an active ingredient.