WO2016021615A1 - Novel compound, method for producing same, and agricultural and horticultural bactericide - Google Patents

Abstract

Provided are: an agricultural and horticultural bactericide having an agricultural and horticultural bactericidal activity; a compound that is represented by formula (1) and is employed as an effective component of said bactericide, and an agriculturally and horticulturally acceptable salt of said compound; and a method for producing said compound by using a microorganism culturing method. (In formula (1), R₁ represents an isopropenyl group or a 1,2-dihydroxypropan-2-yl group, R₂ represents a hydrogen atom or a hydroxyl group, R₃ represents a hydrogen atom or a chlorine atom, R₄ represents an amino group, a methylamino group, or a trimethylamino group, R₅ represents a hydroxyl group or a hydroxymethyl group, and R₆ represents a hydrogen atom or a methyl group.)

Description

Novel compound and production method thereof, agricultural and horticultural fungicide

The present invention relates to a novel compound, an agricultural and horticultural fungicide containing the compound as an active ingredient, a method for protecting plants from plant diseases using these, and a method for producing the compound.

A lot of agricultural and horticultural fungicides have been found so far, but new drugs are still required due to increased drug resistance. International Publication No. WO2001 / 022986 (Patent Document 1), Toxicon, 1983, 21 (Suppl. 3), p. 149-152 (Non-Patent Document 1) and Tetrahedron, 1989, 45 (Issue 8), p. 2351-2372 (Non-patent Document 2) reports that a compound called homopsin A has anticancer activity. However, these documents do not describe that this compound can be used as an agricultural and horticultural fungicide.

International Publication No. WO2001 / 022986

An object of the present invention is to provide a novel compound that can be used as an active ingredient of an agricultural and horticultural fungicide and a method for producing the same.

As a result of diligent research to achieve the above object, the present inventors have found an active substance having an excellent control effect against phytopathogenic fungi in a fungal culture solution and established a method for producing these active substances. did. Furthermore, it has been found that these active substances are novel compounds having chemical structures represented by the following formulas (2) to (6). Moreover, it discovered that the other novel compound which is represented by following formula (1) and has the outstanding control effect with respect to a phytopathogen can be manufactured from these novel compounds, and completed this invention.

That is, the present invention
[1] A compound represented by the following formula (1) and an agricultural and horticulturally acceptable salt thereof.

[In the formula (1), R ₁ represents an isopropenyl group or a 1,2-dihydroxypropan-2-yl group, R ₂ represents a hydrogen atom or a hydroxyl group, R ₃ represents a hydrogen atom or a chlorine atom, R ₄ represents an amino group, a methylamino group, or a trimethylamino group, R ₅ represents a hydroxyl group or a hydroxymethyl group, and R ₆ represents a hydrogen atom or a methyl group. ].

[2] An agricultural and horticultural fungicide containing at least one compound selected from the group consisting of the compound represented by the formula (1) and an agriculturally and horticulturally acceptable salt thereof.

[3] A method for producing at least one compound selected from the group consisting of the compound represented by the formula (1) and a salt acceptable in agriculture and horticulture,
From the compound represented by the following formula (2), the compound represented by the following formula (3), the compound represented by the following formula (4), the compound represented by the following formula (5) and the compound represented by the following formula (6) Culturing a strain having the ability to produce at least one compound selected from the group consisting of:
From the culture, the compound represented by the formula (2), the compound represented by the formula (3), the compound represented by the formula (4), the compound represented by the formula (5), or the formula (6) And the step of isolating the compound represented by formula (1) to obtain the compound represented by the formula (1) or an agricultural and horticulturally acceptable salt thereof;
The manufacturing method of the compound containing this.

[4] The method for producing a compound according to [3], wherein the strain is a microorganism belonging to the genus Taralomyces or Penicillium.

[5] The strain is a strain having a receipt number of NITE ABP-01785 at the National Institute of Technology and Evaluation of the National Institute of Technology and Evaluation, and its mutant strain, and the National Institute of Technology and Evaluation of the National Institute of Technology and Evaluation. The method for producing a compound according to [3] or [4], which is at least one selected from the group consisting of a strain having a receipt number of NITE ABP-02091 and a mutant strain thereof.

[6] belongs to the genus Talaromyces or Penicillium, the compound represented by the formula (2), the compound represented by the formula (3), the compound represented by the formula (4), A strain having the ability to produce at least one compound selected from the group consisting of a compound represented by formula (5) and a compound represented by formula (6).

[7] A strain belonging to the genus Talalomyces and having a receipt number of NITE ABP-01785 at the National Institute of Technology and Evaluation of the National Institute of Technology and Evaluation, or a mutant thereof, and represented by the above formula (2) At least selected from the group consisting of a compound represented by the formula (3), a compound represented by the formula (4), a compound represented by the formula (5), and a compound represented by the formula (6). A mutant strain capable of producing one kind of compound.

[8] A strain belonging to the genus Penicillium and having a receipt number of NITE ABP-02091 or a mutant strain thereof at the Patent Microorganism Depositary, National Institute of Technology and Evaluation, and represented by the above formula (2) At least selected from the group consisting of a compound represented by the formula (3), a compound represented by the formula (4), a compound represented by the formula (5), and a compound represented by the formula (6). A mutant strain capable of producing one kind of compound.

[9] A method for controlling plant diseases using at least one compound selected from the group consisting of the compound represented by the formula (1) and an agricultural and horticulturally acceptable salt thereof, or the agricultural and horticultural fungicide .

[10] At least one compound selected from the group consisting of the compound represented by the formula (1) and an agricultural and horticulturally acceptable salt thereof, or a plant disease from a plant disease using the agricultural and horticultural fungicide How to protect.
I will provide a.

The present invention can provide a novel compound capable of exhibiting an excellent control effect against phytopathogenic fungi, its agriculturally and horticulturally acceptable salts, and agricultural and horticultural fungicides containing them. Furthermore, this invention can provide the strain which can manufacture the novel compound of this invention and can be used for the method of protecting a plant from a plant disease.

Hereinafter, preferred embodiments of the present invention will be described. The compound of the present invention is a compound represented by the following formula (1) and an agriculturally and horticulturally acceptable salt thereof.

In the formula (1), R ₁ represents the following formula:

Or an isopropenyl group represented by the following formula:

1, 2-dihydroxypropan-2-yl group represented by: R ₂ represents a hydrogen atom or a hydroxyl group, R ₃ represents a hydrogen atom or a chlorine atom, R ₄ represents an amino group, a methylamino group, or A trimethylamino group, R ₅ represents a hydroxyl group or a hydroxymethyl group, and R ₆ represents a hydrogen atom or a methyl group. In the formula (1), the bond indicated by the wavy line is a carbon-carbon single bond, and the imidazole group and the carboxyl group or acetyl group bonded via the carbon-carbon double bond are in a trans or cis positional relationship. (The same applies hereinafter).

In the present invention, a preferred embodiment of the compound is that in the formula (1), R ₁ is an isopropenyl group or a 1,2-dihydroxypropan-2-yl group, and R ₂ is a hydrogen atom or a hydroxyl group. R ₃ is a hydrogen atom or a chlorine atom, R ₄ is an amino group or a methylamino group, R ₅ is a hydroxyl group, and R ₆ is a hydrogen atom, and an agriculturally and horticulturally acceptable salt thereof. (Aspect I)

In the present invention, a more preferable embodiment of the compound is a compound represented by the following formula (2) (hereinafter sometimes referred to as “PF1451A substance”), a compound represented by the following formula (3) (hereinafter sometimes represented by "PF1451B substance"), a compound represented by the following formula (4) (hereinafter sometimes referred to as "PF1451C substance"), a compound represented by the following formula (5) (hereinafter sometimes referred to as "PF1451D substance"), A compound represented by the formula (6) (hereinafter referred to as “PF1451E substance” in some cases) and an agriculturally and horticulturally acceptable salt thereof (Aspect II). In the following cases, the PF1451A substance, the PF1451B substance, the PF1421C substance, the PF1451D substance, or the PF1451E substance are collectively referred to as “PF1451 substance”.

In the present invention, examples of the agriculturally and horticulturally acceptable salts include alkali metal salts such as sodium salts and potassium salts; alkaline earth metal salts such as calcium salts and barium salts; hydrochlorides, sulfates, nitrates, phosphorus Inorganic acid salts such as acid salts; organic acid salts such as acetates, citrates and benzoates.

The compound of the present invention, that is, the compound represented by formula (1) and its agriculturally and horticulturally acceptable salt are at least one selected from the group consisting of PF1451A substance, PF1451B substance, PF1451C substance, PF1451D substance and PF1451E substance. Cultivate a strain (producing strain) capable of producing the above compound, purify and isolate the PF1451A substance, PF1451B substance, PF1451C substance, PF1451D substance, and PF1451E substance from the culture, and substitute the substituents as necessary. Can be manufactured.

As a strain having the ability to produce PF1451 substance (hereinafter, referred to as “PF1451 substance-producing bacterium”), for example, a filamentous fungus isolated from the soil of Fukuoka Prefecture by the present inventors and belonging to the genus Talalomyces , A strain whose receipt number is NITE ABP-01785 (Talaromyces sp. PF1451: In some cases, simply referred to as “PF1451 strain” in some cases) A strain (Penicillium swiecickii) with a receipt number of NITE ABP-02091 at the National Institute of Technology and Evaluation of the National Institute of Technology and Evaluation. Or, Penicillium kojigenum PF1458: In some cases, simply referred to as “PF1458 strain”).

In addition, the PF1451 substance-producing bacteria may be any strain that has the ability to produce at least one PF1451 substance selected from the group consisting of PF1451A substance, PF1451B substance, PF1451C substance, PF1451D substance, and PF1451E substance, Examples also include passaging strains, artificial mutant strains, natural mutant strains and genetically modified strains of PF1451 strain or PF1458 strain. As such a PF1451 substance-producing bacterium, the 28S rDNA-D1 / D2 base sequence is a strain having a base sequence having 80% or more homology with the PF1451 strain 28S rDNA-D1 / D2 base sequence (SEQ ID NO: 1). A strain in which the 28S rDNA-D1 / D2 base sequence is a base sequence having 80% or more homology with the 28S rDNA-D1 / D2 base sequence (SEQ ID NO: 4) of the PF1458 strain, 85% or more (for example, 85% or more, 90% or more, 95% or more, 98% or more, 99% or more). Moreover, as a PF1451 substance-producing bacterium, a strain whose ITS-5.8S rDNA base sequence is a base sequence having 80% or more homology with the ITS-5.8S rDNA base sequence (SEQ ID NO: 2) of the PF1451 strain; ITS- Examples include strains whose 5.8S rDNA base sequence is a base sequence having 80% or more homology with the ITS-5.8S rDNA base sequence of PF1458 strain (SEQ ID NO: 5). The homology is 85% or more ( For example, 85% or more, 90% or more, 95% or more, 98% or more, 99% or more) is more preferable. The PF1451 substance-producing bacterium is not limited to the specific strain, and any strain may be used as long as it has the ability to produce the PF1451 substance.

The taxonomic properties of PF1451 and PF1458 strains, the culture method of PF1451 substance-producing bacteria, and the purification and isolation methods of the PF1451 substance represented by the above formulas (2) to (6) are as follows. is there.

[Taxonomy of PF1451 strain]
Bacteriological properties of PF1451 strain (a) Macroscopic morphological observation The growth of PF1451 strain after 3 weeks culture at 25 ° C, and the diameter, surface properties and color tone of the colonies are as follows. The description of the color of the colony was based on Kornerup and Wanscher (1978). In addition, soluble pigment was not observed in all media.
Potato dextrose agar medium: Growth is good, colony diameter is 60-70mm, surface texture is velvety, color is Yellowish green, Greyish green, Greyish yellow.
Malt agar medium: Growth is good, colony diameter is 60-70mm, surface texture is velvety, color is Mustard yellow, Olive yellow.
Oatmeal agar medium: Growth is good, colony diameter is 70-80mm, surface texture is velvety, color tone is Greyish green, White, Yellow.
LCA medium (Miura medium): Growth is normal, colony diameter is 30-40mm, surface texture is velvety, color is Olive yellow, Olive.

(B) Microscopic morphology observation The PF1451 strain was cultured on potato dextrose agar medium, malt agar medium, oatmeal agar medium, LCA medium (Miura medium) at 25 ° C. for 1 to 4 weeks and observed with a microscope.
The vegetative mycelium is formed on or in the agar surface and is colorless and the formation of septal hyphae is observed.
The conidial pattern grows directly from the vegetative mycelium, is colorless and has a smooth surface. A penicillus is formed in which metre is formed from the tip of the conidial pattern and a needle-shaped phialide, which is a conidia-forming cell, is formed at the tip.
The conidia are fiaro-type conidia, which are formed in a chain from the phialide, and are spherical to subspherical, colorless to light brown, 1 cell, and the surface is finely spiny.
Formation of sexual reproductive organs is not observed from culture specimens cultured for about 4 weeks.

(C) Gene analysis The following three types of genetic information necessary for strain identification were analyzed.
“28S rDNA-D1 / D2 nucleotide sequence”: SEQ ID NO: 1
As a result of analyzing the 28S rDNA-D1 / D2 nucleotide sequence of PF1451 strain and performing database search, it showed homology with a plurality of nucleotide sequences of Penicillium marneffei, a kind of Ascomycota, with a 98.9% phasing rate. In the phylogenetic tree created on the basis of the upper sequence obtained by homology search, the PF1451 strain is located in a cluster composed of bacterial species such as Penicillium genus Biverticillium subgenus and Talaromyces genus. Formed.
“ITS-5.8S rDNA base sequence”: SEQ ID NO: 2
As a result of decoding the ITS-5.8S rDNA base sequence of the PF1451 strain and performing a database search, it was found to have a homology of 99.1% with the base sequence of Penicillium primulinum CBS 321.48, Penicillium calidicanium CBS 112002, which is a type of Ascomycota. Indicated. In the phylogenetic tree created on the basis of the upper sequence obtained by homology search, the PF1451 strain was located in a cluster composed of the species of Penicillium subgenus Biverticillium, among which a single phylogenetic branch was formed.
“Β-tubulin gene base sequence”: SEQ ID NO: 3
28S rDNA-D1 / D2 and ITS-5.8S rDNA gene analysis did not result in species identification, so the base sequence was analyzed using the functional gene β-tubulin gene.
As a result of decoding the base sequence of β-tubulin gene of PF1451 strain and searching the database, Talaromyces sp.3 showed a homology of 94.5% with the base sequence of Talaromyces thailandensis CBS 133147, a kind of Ascomycetes. The homology was 94.4 to 95.7% with a plurality of registered base sequences. As a result of molecular phylogenetic analysis by the neighbor binding method, PF1451 strain belongs to the Talaromyces section strain group among the Talaromyces genus, and the base sequence of Talaromyces thailandensis CBS 133147 and multiple base sequences registered in Talaromyces sp.3 A cluster supported with a bootstrap value of 78% was formed, among which a single phylogenetic branch was formed.
From the above 28S rDNA-D1 / D2, ITS-5.8S rDNA and β-tubulin gene analysis, and the results of colony properties and morphology observation, the PF1451 strain is referred to as “Talaromyces sp. PF1451” of the genus Talaromyces. did. This strain was deposited in Japan on December 25, 2013, and was transferred to an international deposit on July 23, 2015, and received as NITE ABP-01785, a patent microorganism of the National Institute of Technology and Evaluation Technology. Received at the depository center.

[Taxonomic properties of PF1458 strain]
Bacteriological properties of PF1458 strain (a) Observation of macroscopic morphology The growth of PF1458 strain after culturing at 25 ° C for 3 weeks, and the surface properties and color tone of the colonies are as follows. In addition, soluble pigment was not observed in all media.
Potato dextrose agar medium: The growth is good, the surface properties are cottony, and the colors are White and Grey.
Oatmeal agar medium: Growth is good, surface texture is cottony, and colors are white and gray.

(B) Gene analysis The following three types of genetic information necessary for strain identification were analyzed.
“28S rDNA-D1 / D2 nucleotide sequence”: SEQ ID NO: 4
A 28S rDNA-D1 / D2 nucleotide sequence of PF1458 strain was analyzed and a database search was performed. As a result, it showed 100% homology with the nucleotide sequence of Penicillium kojigenum NRRL 3442 ^Τ (AF033489), a kind of Ascomycota . Results of the simple molecular phylogenetic analysis, PF1458 strain formed a same system branches and ^{Penicillium kojigenum NRRL 3442 Τ (AF033489)} . The homology between SEQ ID NO: 1 and SEQ ID NO: 4 was 90%.
“ITS-5.8S rDNA base sequence”: SEQ ID NO: 5
As a result of deciphering the ITS-5.8S rDNA base sequence of the PF1458 strain and performing a database search, it showed a homology of 99.5 to 100% with a plurality of base sequences of Penicillium swiecickii, a kind of Ascomycota. As a result of simple molecular phylogenetic analysis, PF1458 strain formed the same phylogenetic branch as Penicillium swiecickii NRRL 918 ^Τ (AF033490). The homology between SEQ ID NO: 2 and SEQ ID NO: 5 was 85%.
From the above 28S rDNA-D1 / D2 and ITS-5.8S rDNA gene analysis results, the PF1458 strain was designated as “Penicillium swiecickii or Penicillium kojigenum PF1458”. This strain was received as the receipt number NITE ABP-02091 as of July 23, 2015 at the National Institute of Technology and Evaluation Patent Microorganism Depositary.

[Culture method of PF1451 substance-producing bacteria]
A preferred embodiment of the method for culturing the PF1451 substance-producing bacterium includes a method of culturing the PF1451 strain or PF1458 strain in a nutrient medium containing an appropriate carbon source and nitrogen source.
The medium used may be either a natural medium or a synthetic medium, and may be either a solid medium or a liquid medium.
As a nutrient source, a known source conventionally used for mold cultivation can be used. For example, as a carbon source, grains such as glucose, sucrose, starch syrup, dextrin, starch, glycerol, molasses, rice, wheat, corn grits; animal and vegetable oils and the like can be used. As nitrogen sources, animal and plant-derived medium components such as soybean flour, wheat germ, corn steep liquor, cottonseed meal, meat extract, peptone, yeast extract, and casein; ammonium sulfate, sodium nitrate, urea and the like can be used. . In addition, it is effective to add inorganic salts that can generate sodium, potassium, calcium, magnesium, cobalt, chlorine, phosphoric acid, sulfuric acid and other ions to the medium as necessary. Furthermore, organic substances and inorganic substances used for the production of the PF1451 substance can be appropriately added to assist the growth of bacteria. If necessary, micronutrients such as vitamins, growth promoting substances, precursors, etc. that promote the growth of PF1451 substance-producing bacteria and the production of PF1451 substance may be added appropriately.

The culture may be performed under aerobic conditions such as stationary culture, shaking culture or aeration and agitation culture. It is preferable to perform the culture in the vicinity of neutral pH in liquid culture. A suitable temperature for culturing is 25 to 40 ° C. Production of the PF1451 substance varies depending on the medium and culture conditions, but in any of stationary culture, shaking culture, and tank culture, the accumulation usually reaches its maximum in 2 to 20 days. When the accumulation of the target substance among the PF1451 substances in the culture reaches the maximum, the culture is stopped. The culture conditions such as medium composition, medium liquidity, culture temperature, stirring speed, and aeration rate can be adjusted and selected as appropriate according to the type of strain used and external conditions. it can. In liquid culture, when there is foaming, antifoaming agents such as silicon oil, vegetable oil, and surfactant can be used as appropriate. Since the PF1451 substance accumulated in the culture thus obtained is contained in the cells and in the culture filtrate, it is preferable to extract the PF1451 substance by solvent extraction of the culture.

[PF1451 substance purification and isolation]
Based on the properties of the PF1451 substance of the present invention from the culture, a normal separation means such as a solvent extraction method, an ion exchange resin adsorption method or a distribution chromatography method, a gel filtration method, a dialysis method, a precipitation method and the like are appropriately used. It is possible to purify and isolate in combination.
Specifically, after the organic solvent of the extract obtained by solvent extraction from the culture was distilled off and concentrated, the resulting concentrate was used as a synthetic adsorbent (for example, Diaion HP-20, Mitsubishi Condensed under reduced pressure, a passing liquid obtained by passing through a chemical) or an extraction liquid obtained by extraction with a solvent system such as acetone / water or methanol / water after passing through the synthetic adsorbent. The obtained concentrate was repeatedly used in a solvent system such as methanol / chloroform, acetone / hexane, ethyl acetate / hexane, methanol / water, or acetonitrile / water, and silica gel chromatography (for example, Wako Gel C300, Wako Pure Chemical Industries, Ltd.). And ODS chromatography (for example, Cosmo Seal 75 C18-OPN, manufactured by Nacalai Tesque; TSKgel-amide-80, manufactured by Tosoh Corporation) and the like. If necessary, it can be purified and isolated by elution with methanol, water, etc. using gel filtration column chromatography such as Sephadex LH-20 (Amersham Biosciences AB). .

The compound represented by the above formula (1) of the present invention and its agriculturally and horticulturally acceptable salt are such that the target compound represented by the above formula (1) is a PF1451A substance, a PF1451B substance, a PF1421C substance, a PF1451D substance or a PF1451E substance. In this case, it can be obtained by the method described in the purification method and isolation method of the above PF1451 substance. Further, when the target compound represented by the formula (1) is a compound other than the PF1451 substance, R ₁ to R ₆ can be appropriately selected from known methods based on the PF1451 substance obtained by the above method. A compound represented by the formula (1) can be obtained by substituting a group at a position with a target group. As such a method, for example, when the methylamino group of the PF1451A substance is changed to a trimethylamino group, a method of adding hydrochloric acid and trimethylsilyldiazomethane to the methanol solution of the PF1451A substance and reacting them can be employed. In addition, these compounds can be appropriately converted into the above-mentioned agricultural and horticulturally acceptable salts by known methods.

The compound represented by the formula (1) according to the present invention and an agricultural and horticulturally acceptable salt thereof (preferably the above-mentioned embodiment I, more preferably the above-mentioned embodiment II), and at least one of these. The agricultural and horticultural fungicide has an excellent control effect against plant pathogens. The plant pathogen is not particularly limited, for example,
Brown sugar beet fungus (Cercospora beticola), black root fungus (Aphanomyces cochlloides), root rot fungus (Thanatephorus cucumeris), leaf rot fungus (Thanatephorus cucumeris), downy mildew (Peronospora schachtii);
Phytophthora infestans, scab (Streptomyces scabies, Streptomyces acidiscabies), summer plague (Alternaria solani);
"Peanut" brown spot fungus (Mycosphaerella arachidis), black astringent fungus (Mycosphaerella berkeleyi);
"Cucumber" powdery mildew (Sphaerotheca fuliginea), downy mildew (Pseudoperonospora cubensis), vine wilt (Mycosphaerella melonis), vine split fungus (Fusarium oxysporum), mycorrhizal fungus (Sclerotinia sclerotiorum), gray fungus cine ), Anthracnose fungus (Colletotrichum orbiculare), black spot fungus (Cladosporium cucumerinum), brown spot fungus (Corynespora cassicola), seedling blight fungus (Pythium debaryanam, Rhizoctonia solani Kuhn), spotted bacterial fungus (Pseudomonas syringmans pry.
"Tory" gray mold fungus (Botrytis cinerea), leaf mold fungus (Cladosporium fulvum), Phytophthora infestans;
"Golden" gray mold fungus (Botrytis cinerea), black blight fungus (Corynespora melongenae), powdery mildew fungus (Erysiphe cichoracearum), subtilis fungus (Mycovellosiella nattrassii), brown rot fungus (Phytophthora capsici);
"Strawberry" gray mold fungus (Botrytis cinerea), powdery mildew fungus (Sohaerotheca humuli), anthracnose fungus (Colletotrichum acutatum, Colletotrichum fragariae), Phytophthora cactorum;
"Onion" gray rot fungus (Botrytis allii), gray mold fungus (Botrytis cinerea), white spotted fungus (Botrytis squamosa), downy mildew (Peronospora destructor);
“Cabbage” root-knot fungus (Plasmodiophora brassicae), soft-rot fungus (Erwinia carotovora), downy mildew (Peronospora parasitica);
“Daikon” sclerotia (Sclerotinia sclerotiorum), white rust (Albugo macrospora), anthrax (Colletotrichum higginsianum);
Lettuce downy mildew (Bremia lactucae), powdery mildew (Erysiphe cichoracearum), mycorrhizal fungus (Sclerotinia sclerotiorum), gray mold (Botrytis cinerea);
"Pea" downy mildew (Peronospora pisi), powdery mildew (Erysiphe pisi), brown spot (Mycosphaerella pinodes);
"Bora bean" downy mildew (Peronospora viciae), white silkworm (Sclerotinia rolfsii);
"Ingen" sclerotia (Sclerotinia sclerotiorum), gray mold (Botrytis cinerea);
"Apple" powdery mildew (Podosphaera leucotricha), black rot (Venturia inaequalis), monilinia (Monilinia mali), black spot (Mycosphaerella pomi), rot (Valsa mali), leaf spot (Alternaria mali), red rot (Gymnosporangium yamadae), ring rot fungus (Botryosphaeria berengeriana), anthracnose fungus (Glomerella cingulata, Colletotrichum acutatum), brown spot fungus (Diplocarpon mali), soot spot fungus (Zygophiala jamaicensis), soot spot fungus (Gloeodes pomi
“Oyster” powdery mildew (Phyllactinia kakicola), anthracnose fungus (Gloeosporium kaki), keratodeciduous fungus (Cercospora kaki);
"Peach" astronomical fungus (Monilinia fructicola), black rot fungus (Cladosporium carpophilum), homopsis spoilage fungus (Phomopsis sp.);
Mongolia fructicola of “auto cherry”;
"Grape" gray mold fungus (Botrytis cinerea), powdery mildew fungus (Uncinula necator), late rot fungus (Glomerella cingulata, Colletotrichum acutatum), downy mildew fungus (Plasmopara viticola), black mold fungus (Elsinoe ampelina), brown spot fungus (Pseudocercospora vitis), black rot fungus (Guignardia bidwellii);
"Pear" black rot fungus (Venturia nashicola), red rot fungus (Gymnosporangium asiaticum), black spot fungus (Alternaria kikuchiana), ring rot fungus (Botryosphaeria berengeriana), powdery mildew (Phyllactinia mali);
“Chesta” ring rot fungus (Pestalotia theae), anthracnose fungus (Colletotrichum theae-sinensis);
Citrus scab (Elsinoe fawcetti), green mold (Penicillium italicum), green mold (Penicillium digitatum), gray mold (Botrytis cinerea), black spot fungus (Diaporthe citri), mold fungus (Xanthomonas campestris pv.Citri) );
"Wheat" powdery mildew (Erysiphe graminis f.sp.tritici), red mold fungus (Gibberellazeae), red rust fungus (Puccinia recondita), brown snow rot fungus (Pythium iwayamai, Pythium paddicum, Pythium okanoganense), red snow rot fungus (Monographella nivalis), eye-opening fungus (Pseudocercosporella herpotrichoides), leaf blight fungus (Septoria tritici), blight fungus (Leptosphaeria nodorum), snow mold fungus (Typhula incarnata), snow mold fungus (Myriosclerotinia borealis) , Gaeumanomyces graminis;
"Barley" leafy spot fungus (Pyrenophora graminea), cloud fungus (Rhynchosporium secalis), naked smut fungus (Ustilago tritici, U.nuda), brown snow rot fungus (Pythium iwayamai, Pythium paddicum, Pythium okanoganense);
Rice blast fungus (Pyricularia oryzae), blight fungus (Rhizoctonia solani), idiot seedling fungus (Gibberella fujikuroi), sesame leaf blight fungus (Cochliobolus miyabeanus), seedling blight fungus (Pythium graminicola), white leaf blight fungus ( Xanthomonas oryzae), Burkholderia plantarii, Brown bacterium (Acidovorax avenae), Burkholderia glumae;
"Sunflower" downy mildew (Plasmopara halstedii);
“Tobacco” Sclerotinia sclerotiorum, powdery mildew (Erysiphe cichoracearum), Phytophthora nicotianae;
“Tulip” gray mold fungus (Botrytis cinerea);
"Bentgrass" Snow rot large-scale sclerotia (Sclerotinia borealis), red fire rot (Pythium aphanidermatum); and "Orchardgrass" powdery mildew (Erysiphe graminis)
Is mentioned.

Among these, as preferred plant pathogenic bacteria to be applied,
"Phantom" black root fungus (Aphanomyces cochlloides), downy mildew (Peronospora schachtii);
Phytophthora infestans of "potato";
"Cucumber" downy mildew (Pseudoperonospora cubensis), seedling blight (Pythium debaryanam);
Phytophthora infestans of "Tomato";
Brown eggplant rot fungus (Phytophthora capsici);
Phytophthora cactorum of "strawberry";
"Onion" downy mildew (Peronospora destructor);
"Cabbage" downy mildew (Peronospora parasitica);
"Daikon" white rust fungus (Albugo macrospora);
Lettuce downy mildew (Bremia lactucae);
"Pea" downy mildew (Peronospora pisi);
"Sola beans" downy mildew (Peronospora viciae);
“Grape” downy mildew (Plasmopara viticola);
"Wheat" brown snow rot fungus (Pythium iwayamai, Pythium paddicum, Pythium okanoganense);
Brown barley snow rot fungus (Pythium iwayamai, Pythium paddicum, Pythium okanoganense);
"Rice" seedling blight fungus (Pythium graminicola);
"Sunflower" downy mildew (Plasmopara halstedii);
Phytophthora nicotianae; "Bentgrass" Pythium aphanidermatum
And the like. The compound or agricultural / horticultural fungicide of the present invention controls plant diseases caused by these fungi.

The agricultural and horticultural fungicide of the present invention contains at least one of the compound represented by the above formula (1) and the salt that is acceptable for agriculture and horticulture (hereinafter referred to as “the present compound”). As the agricultural and horticultural fungicide, for example, it was isolated from a culture obtained by culturing PF1451 substance-producing bacteria, and the present compound obtained by substituting substituents as necessary was used as a fungicide. And a mixture of the compound of the present invention and a carrier, a culture obtained by culturing a PF1451 substance-producing bacterium, and a mixture of the culture and a carrier. In the present invention, when a PF1451 substance is used as the compound of the present invention, even if the aforementioned PF1451 substance-producing bacterium is used as it is, an excellent control effect against phytopathogenic fungi is exhibited.

Examples of the agricultural and horticultural fungicides include other fungicides, insecticides, acaricides, nematicides and other anthelmintic agents, herbicides, plant growth regulators and other agents; Pesticide; fertilizer and the like may be further contained.

Examples of such drugs include those described in the Pesticide Manual (13th edition, published by The British Crop Protection Council) and Shibuya Index (SHIBUYA INDEX 16th edition, 2012, published by SHIBUYA INDEX RESEARCH GROUP).

More specifically, examples of the insecticide, acaricide and anthelmintic agent include the drugs shown in the following A-1 to A-26.
A-1. Organophosphorus insecticides include acephate, dichlorvos, EPN, fenitrothion, fenamifos, prothiofos, profenfos, pyraclofos, chlorpyrifos methyl (chlorpyrifosmethyl) methyl), diazinon, fosthiazate, and imimiafos.
A-2. Carbamate insecticides include mesomyl, thiodicarb, aldicarb, oxamyl, propoxur, carbaryl, fenobucarb, ethiofencarb, fenothiocarb, and fenothiocarb. ), Pirimicarb, carbofuran, benfuracarb, triazamate.
A-3. As pyrethroid insecticides, acrinathrin, allethrin, bifenthrin, bioallethrin, bioresmethrin, cyfluthrin, cyphenothrin ), Empetrin (fluenthrin), flumethrin (flumethrin), halfenprox (halfenprox), imiprothrin (imiprothrin), methfurthrin (metofluthrin), phenothrin (phenothrin), praretrin (profluthrin), threthrin (pythrrin) (Resmethrin), tetramethrin, tralomethrin, transfluthrin, permethrin, tefluthrin, cypermethrin, deltamethrin deltamethrin), cyhalothrin (cyhalothrin), fenvalerate (fenvalerate), fluvalinate (fluvalinate), etofenprox (ethofenprox), include silafluofen (silafluofen) it is.
A-4. Juvenile hormone-like compounds include hydroprene, metoprene, kinoprene, phenoxycarb, and pyriproxyfen.
A-5. Nicotine receptor agonists and antagonists include imidacloprid, clothianidin (c1othianidin), thiamethoxam, acetamiprid, acetamiprid, nitenpyram, thiacloprid, dinotefuran, dinotefuran, dinotefuran (note) spinosad, spinetoram, sulfoxaflor, flupyradifurone, cartap, thiocyclam, bensultap, and thiosultap.
A-6. Examples of GABAergic chloride channel antagonists include ethiprole, fipronil, pyrafluprole, pyriprole, and endosulfan.
A-7. Examples of the chloride channel active compound include abamectin, milbemectin, lepimectin, and emamectin benzoate.
A-8. Mitochondrial respiratory chain complex I inhibitors include pyridaben, fenpyroxymate, pyrimidifen, tebufenpyrad, tolfenpyrad, and fenazaquin.
A-9. Mitochondrial respiratory chain complex II inhibitors include cyenopyrafen, pyflbumide, and cyflumetofen.
A-10. Mitochondrial respiratory chain complex III inhibitors include fluacrypyrim, acequinocyl, and hydramethylnon.
A-11. An example of an uncoupler is chlorfenapyr.
A-12. Other oxidative phosphorylation inhibitors include azocyclotin, cyhexatin, diafenthiuron, fenbutatin oxide, propargite, and tetradifon. Can be mentioned.
A-13. Examples of molting inhibitors include cyromazine, chromafenozide, halofenozide, methoxyfenozide, tebufenozide.
A-14. Examples of synergists include piperonyl butoxide and tribufos.
A-15. Sodium channel inhibitors include indoxacarb and metaflumizone.
A-16. Examples of fumigants include methyl bromide and chloropicrin sulfuryl fluoride.
A-17. Selective feeding inhibitors include crylotie, pymetrozine, flonicamid.
A-18. Examples of mite growth inhibitors include clofentezine, hexythiazox, and ethoxazole.
A-19. Chitin biosynthesis inhibitors include buprofezin, bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron ), Hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron, triflumuron.
A-20. Examples of lipid biosynthesis inhibitors include spirodiclofen, spiromesifen, and spirotetramat.
A-21. Examples of octopamine-like substances include amitraz, chlordimeform, demiditraz, clenpirin, and cymiazole.
A-22. Ryanodine receptor agonists include flubendizmide.
A-23. Isoxazole derivatives include 4- [5- (3,5-Dichloro-phenyl) -5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl] -2-methyl-N-pyridin-2 -ylmethyl-benzamide), 4- [5- (3,5-Dichloro-phenyl) -5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl] -2-methyl-N- (2,2,2 -trifluoro-ethyl) -benzamide, 4- [5- (3,5-Dichloro-phenyl) -5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl] -2-methyl-N-[(2, 2,2-trifluoro-ethylcarbamoyl) -methyl] -benzamide (Fluralaner), 4- [5- (3,5-Dichloro-phenyl) -5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl] -naphthalene -1-carboxylic acid [(2,2,2-trifluoro-ethylcarbamoyl) -methyl] -amide, 4- [5- (3,5-Dichlorophenyl) -5-trifluoromethyl-4,5-dihydro-isoxazol-3- yl] -N-[(methoxyimino) methyl] -2-methylbenzamide, 4- [5- (3-Chloro-5-trifluoromethyl-phenyl) -5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]- 2-methyl-N-[(2,2,2-trifluoro-ethylcarbamoyl) -methyl] -benzamide, 4- [5- (3-Chloro-5-trifluoromethyl-phenyl) -5-trifluoromethyl-4,5-dihydro -isoxazol-3-yl] -naphthalene-1-carboxylic acid [(2,2,2-trifluoro-ethylcarbamoyl) -m ethyl] -amide (Afoxolaner), 5- [5- (3,5-Dichloro-4-fluoro-phenyl) -5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl] -2- [1,2 , 4] triazol-1-yl-benzonitrile.
A-24. As anthranilic acid amide compounds, chlorantraniliprole, cyantraniliprole, cyclaniliprole, tetraniliprole, and international publication No. WO2007 / Examples include substances described in No. 006670, International Publication No. WO2013 / 024008, International Publication No. WO2013 / 024009, International Publication No. WO2014 / 053406, or acid addition salts thereof.
A-25. Examples of the microbial insecticide include Bacillus thuringiensis subsp. Israelensi, Bacillus sphaericus, Bacillus thuringiensis subsp. Tenebrionis.
A-26. Other insecticides include dicofol, bifenazate, pyridalyl, pyrifluquinazon, flometoquin, afidopyropen, triflumezopyrim, triflumezopyrim Dichloromezothiaz, amidoflumet, organometallic compounds, dinitro compounds, organosulfur compounds, urea compounds, triazine compounds, hydrazine compounds, substances represented by the following formulas or acid addition salts thereof Is mentioned.

Further, as other insecticides, compounds represented by the following formula (A) or the following formula (B) described in International Publication No. WO2012 / 029672 and International Publication No. WO2013 / 129692 and their agricultural and horticultural acceptable Salt.

[In the formula (A),
Ar is substituted with any one of a halogen atom, a hydroxyl group, a C1-6 alkyl group optionally substituted with a halogen atom, a C1-6 alkyloxy group optionally substituted with a halogen atom, a cyano group, and a nitro group. An optionally substituted pyridyl group; or a halogen atom, a C1-4 alkyl group optionally substituted by a halogen atom, a C1-4 alkyloxy group optionally substituted by a halogen atom, a hydroxyl group, a cyano group, and Represents a pyrimidyl group optionally substituted by any of the nitro groups;
Y represents a hydrogen atom, a halogen atom, a hydroxyl group, a C1-6 alkyl group optionally substituted by a halogen atom, a C1-6 alkyloxy group optionally substituted by a halogen atom, a cyano group, or a nitro group. ,
R ₁ represents a C 1-6 alkyl group substituted by a halogen atom].

[In the formula (B)
Ar is substituted with any of a halogen atom, a hydroxyl group, a C1-6 alkyl group optionally substituted with a halogen atom, a C1-6 alkyloxy group optionally substituted with a halogen atom, a cyano group, or a nitro group. An optionally substituted pyridyl group; or a halogen atom, a C1-4 alkyl group optionally substituted by a halogen atom, a C1-4 alkyloxy group optionally substituted by a halogen atom, a hydroxyl group, a cyano group, or Represents a pyrimidyl group optionally substituted by any of the nitro groups;
R ₁ represents a C 1-6 alkyl group substituted by a halogen atom].

Examples of other fungicides include the drugs shown in the following B-1 to B-18.
B-1. Examples of nucleic acid synthesis inhibitors include benalaxyl, benalaxyl-M (benalaxyl-M), furaxyl (furalaxyl), metalaxyl (metalaxyl), metalaxyl-M (metalaxyl-M), oxadixyl (oxadixyl) , Offurace, bupirimate, dimethirimol, ethirimol, hymexazole, octhilinone, oxolinic acid and the like.
B-2. Examples of mitotic and mitotic inhibitors include benomyl, carbendazim, fuberidazole, thiabendazole, thiophanate, thiophanate-methyl, Examples include dietofencarb, zoxamide, ethaboxam, pencycuron, and fluopicolide.
B-3. Examples of the complex I inhibitor include diflumetorim, tolfenpyrad and the like.
B-4. As complex II inhibitors, for example, benodanil, flutolanil, mepronil, isofetamid, fluopyram, fenfuram, carboxin, carboxin, Oxycarboxin, thifluzamide, benzovindiflupyr, bixafen, fluxapyroxad, furametpyr, isoprazam, penflufen, penflufen penthiopyrad), sedaxane, boscalid and the like.
B-5. Complex III inhibitors include, for example, azoxystrobin, coumoxystrobin, enoxastrobin, flufenoxystrobin, picoxystrobin ( picoxystrobin), pyraoxystrobin, pyraclostrobin, pyrametostrobin, triclopyricarb, cresoxim-methyl, trifloxystrobin, dimoxist Robin (dimoxystrobin), phenaminostrobin, metominostrobin, oryastrobrobin, famoxadone, fluoxastrobin, mandestrobin, pyriminostrobin ( pyriminostrobi n), fenamidone, pyribencarb, cyazofamid, amisulbrom, ametoctradin and the like.
B-6. Examples of the uncoupling agent for oxidative phosphorylation include binapacryl, meptyldinocap, dinocap, fluazinam and the like.
B-7. Examples of the oxidative phosphorylation inhibitor include fentin acetate, fentin chloride, fentin hydroxide and the like.
B-8. Examples of ATP synthesis inhibitors include silthiofam.
B-9. Examples of amino acid and protein synthesis inhibitors include cyprodinil, mepanipyrim, pyrimethanil, blasticidin-S, kasugamycin, streptomycin, Examples thereof include oxytetracycline.
B-10. Signaling inhibitors include, for example, quinoxyfen, proquinazid, fenpiclonil, fludioxonil, fludioxonil, chlozolinate, iprodione, procymidone, procymidone, vinclozolin).
B-11. Examples of lipid and cell membrane synthesis inhibitors include edifenphos, iprobenfos, pyrazophos, isoprothione, biphenyl, chloroneb, dichlorane ( and dicloran, quintozene, tecnazene, tolclofos-methyl, etridiazole, iodocarb, propamocarb, prothiocarb and the like.
B-12. Examples of membrane sterol synthesis inhibitors include triforine, pyrifenox, pyrizoxazole, fenarimol, nuarimol, imazalil, oxypoconazole ( oxpoconazole, pefurazoate, prochloraz, triflumizole, azaconazole, bitertanol, bromuconazole, cyproconazole, difenoconazole, difenoconazole (Diniconazole), epoxiconazole, etaconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, Hexaconazole, imibenconazole, ipconazole, metconazole, microbutanil, penconazole, propiconazole, simeconazole, tebuconazole, tebuconazole Tetraconazole, triadimefon, triadimenol, triticonazole, prothioconazole, aldimorph, dodemorph, fenpropimorph, tridemorph (Tridemorph), fenpropidin, piperalin, spiroxamine, fenhexamid, fenpyrazamine, piributicalbu pyributicarb), naftifine (naftifine), terbinafine (terbinafine), and the like.
B-13. Cell wall biosynthesis inhibitors include, for example, validamycin, polyoxin, dimethomorph, flumorph, pyrimorph, benchthiavalicarb, iprovalicarb ), Varilifenalate, mandipropamid and the like.
B-14. Examples of melanin synthesis inhibitors for cell walls include fthalide, pyroquilon, tricyclazole, carpropamid, diclocymet, fenoxanil and the like.
B-15. Examples of host plant resistance inducers include acibenzolar-S-methyl, probenazole, thiadinyl, isothianil, laminarin and the like. Can be mentioned.
B-16. Examples of the multi-acting point contact activator include copper, sulfur, ferbam, mancozeb, maneb, metiram, propineb, Thiram, zineb, ziram, captan, captafol, folpet, chlorothalonil, dichlofluanid, tolylfluanid, guazatine ), Iminoctadine, anilazine, dithianon, quinoxaline (chinomethionat / quinomethionate), fluoroimide and the like.
B-17. Other fungicides include, for example, cymoxanil, fosetyl-Al, phosphorous acid and salts, teclofthalam, triazoxide, flusulfamide, Diclomezine, methasulfocarb, cyflufenamid, metrafenone, pyriofenone, dodine, flutolanil, ferimzone, tebufloquin, tebufloquin, tebufloquin Proline (oxathiapiprolin), pyraziflumid (pyraziflumid, NNF-0721), MIF-1002, picarbutrazox, NF-171, tolprocarb, pydiflumetofen, KUF-1411, S-2399 Etc.
B-18. As plant disease control agents, JP2009-078991A, JP2009-073823A, International Publication No. WO2008 / 102678, JP2010083763A, International Publication No. WO08 / 066614, International Publication No. WO09 / 028280, International Publication No. WO05 / 115994, JP-A-2006-290883, International Publication No. WO07 / 072999, International Publication No. WO07 / 108483, International Publication No. WO08 / 062878, International Publication No. WO06 / 098128 The compounds described in No. are listed.

The carrier may be any pharmaceutically acceptable carrier, and examples thereof include a solid carrier, a liquid carrier, and a gaseous carrier. The agricultural and horticultural fungicides include emulsions, solutions, suspensions, water, and the like. It is provided as an arbitrary dosage form such as a summing agent, flowable agent, powder agent, granule, tablet, oil agent, aerosol agent, smoke agent and the like. In addition, the agricultural and horticultural fungicide may further contain surfactants and dispersants for emulsification, dispersion, spreading, etc., and other formulation adjuvants for improving the properties of other formulations. Good. These carriers, surfactants, dispersants, and lumbering aids can be used alone or in combination as required.

Examples of the solid carrier include talc, bentonite, clay, kaolin, diatomaceous earth, vermiculite, white carbon, calcium carbonate, and the like.

Examples of the liquid carrier include alcohols such as methanol, n-hexanol and ethylene glycol; ketones such as acetone, methyl ethyl ketone and cyclohexanone; aliphatic hydrocarbons such as n-hexane, kerosene and kerosene; toluene, xylene and methyl Aromatic hydrocarbons such as naphthalene; Ethers such as diethyl ether, dioxane and tetrahydrofuran; Esters such as ethyl acetate; Nitriles such as acetonitrile and isobutyronitrile; Acid amides such as dimethylformamide and dimethylacetamide; Vegetable oils such as oil and cottonseed oil; dimethyl sulfoxide, water and the like.

Examples of gaseous carriers include LPG, air, nitrogen, carbon dioxide, dimethyl ether and the like.

Examples of the surfactant and dispersant include alkyl sulfates, alkyl (aryl) sulfonates, polyoxyalkylene alkyl (aryl) ethers, polyhydric alcohol esters, and lignin sulfonate.

Examples of the lumber adjuvant include carboxymethyl cellulose, gum arabic, polyethylene glycol, calcium stearate and the like.

The content of the active ingredient in the agricultural and horticultural fungicide, that is, the compound of the present invention is not particularly limited, but usually 0.5 to 75% by weight in the emulsion, 0.05 to 25% by weight in the powder, hydrated 0.5 to 90% by weight for agents and 0.05 to 50% by weight for granules.

The method for protecting plants from plant diseases according to the present invention comprises at least one of the compound represented by the formula (1) and its agriculturally and horticulturally acceptable salt (the compound of the present invention), or the agricultural and horticultural sterilization. Use the agent. Examples of such methods include the compound of the present invention or the agricultural and horticultural fungicide, and the other fungicides, insecticides, acaricides, nematicides and other anthelmintic agents, herbicides, plant growth regulators and the like. A method in which a microbial pesticide such as an entomopathogenic virus agent is used in combination may be used.

Examples of the plant include useful crops, specifically sugar beet, groundnut, potato, cucumber, tomato, eggplant, strawberry, onion, cabbage, radish, lettuce, pea, broad bean, green beans, apple, oyster, peach, sweet potato, grape , Pear, tea, wheat, barley, rice, sunflower, tobacco, tulip, bentgrass, orchardgrass, and genetically modified crops of these plants.

As a method for protecting plants from plant diseases, an effective amount of the compound of the present invention or the agricultural and horticultural fungicide is applied to plant stems and leaves, seeds, roots, bulbs (for example, tubers, tubers, corms, rooted bodies, bulbs, etc.) ), Germinated plants, seedlings, soil, and methods for application to cultivation materials and the like.

When the application target is plant seeds, roots, bulbs (for example, tuberous roots, tubers, corms, root support bodies, bulbs, etc.), suitable examples of application methods include osmotic transfer of active ingredients into the plant body. The method is not particularly limited as long as it does not hinder, but includes a dipping method, a powder coating method, a smearing method, a spraying method, a pellet method, a film method and the like.
The dipping method is a method in which seeds are immersed in a liquid drug solution. The powder coating method includes a dry powder coating method in which a powdered drug is attached to dry seeds, and a seed lightly soaked in water. There is a wet powder coating method to attach the drug in the shape. In addition, there are a smearing method in which a suspended drug is applied to the seed surface in a mixer and a spraying method in which the suspension is sprayed onto the seed surface. In addition, when pelletizing seeds with a filler into a certain size and shape, the pellet method in which the filler is mixed with the chemical, the coating method in which the seed is coated with a film containing the chemical, and in a sealed container There is a fumigation method in which seeds are disinfected with a gasified chemical.

When applied to seeds, roots, bulbs (eg, tuberous roots, tubers, bulbs, rooted bodies, bulbs, etc.) by the dipping method, seeds, roots, bulbs (eg, tuberous roots, tubers, bulbs, bulbous bodies, bulbs, etc.) And the like may be planted or soaked for a time sufficient for the active ingredient to penetrate into the plant. In this case, the immersion time and temperature can be appropriately determined according to the application target, the amount of the active ingredient, and the like. For example, the permeation transfer time is not particularly limited, but is 1 hour or more. The temperature is 5 to 45 ° C. although not particularly limited.

When the application object is a germinated plant and a young plant, the whole or a part of the plant body is treated by immersion with the agricultural and horticultural fungicide after germination, after emergence from soil, or before transplantation. This can protect these plants.

When the application target is soil, an application method includes, for example, a method of applying the agricultural and horticultural fungicide in a dosage form such as a granule or a liquid into or on the soil. Preferable soil application methods include spraying, strips, grooves, and planting holes. Here, the spraying treatment includes surface treatment over the entire area to be treated, and subsequent mechanical introduction into the soil. Moreover, it is also an advantageous soil application method to apply by irrigating the solution which emulsified or melt | dissolved this invention compound or the said agricultural and horticultural fungicide in water.

When the application target is a cultivation material, the application method includes, for example, a hydroponic liquid medium; a solid medium such as sand culture, NFT (Nutrient Film Technology), rock wool culture; an artificial culture medium containing vermiculite, and An effective amount of the compound of the present invention or the agricultural and horticultural fungicide can be directly applied to materials for cultivation such as artificial mats for raising seedlings.

The effective amount can be appropriately determined in consideration of the type and amount of the application target, temperature, etc. For example, when the application target is seeds, the compound of the present invention is applied in an amount of 1 to 10 kg per 10 kg of seeds. The

In the case of treating the plant foliage, the compound of the present invention is applied in an amount of 0.1 to 10 kg per 10 ares of cultivated land.

When applied to soil, the compound of the present invention is applied in an amount of 0.1 g to 10 kg per 10 ares of arable land.

EXAMPLES Examples and test examples of the present invention will be shown below, but the present invention is not limited to these examples, and includes all the modifications or modification means not shown here.

(Production Example 1)
[Incubation of PF1451 substance-producing bacteria]
As a seed medium, a medium composed of 2.0% starch (starch), 1.0% glucose (glucose), 0.5% polypeptone, 0.6% wheat germ, 0.3% yeast extract, 0.2% soybean meal and 0.2% calcium carbonate (pH7 before sterilization) .0) was used. As the solid production medium, brown rice that has sufficiently absorbed water and 0.3% soybean meal is used. As the liquid production medium, starch (starch) 2.0%, glucose (glucose) 1.0%, polypeptone 0.5 %, Wheat germ 0.6%, yeast extract 0.3%, soybean meal 0.2% and calcium carbonate 0.2% (medium pH 7.0 before sterilization) was used.

(Culture Example 1)
80 mL of the above seed medium was dispensed and PF1451 strain was inoculated into 100 500 mL Erlenmeyer flasks sterilized at 121 ° C. for 20 minutes, followed by shaking culture at 25 ° C. for 3 days to obtain a seed culture solution. Next, 4 kg of solid production medium was placed in 50 pairs of deep bats with 4.5L stainless steel lids and sterilized at 121 ° C for 20 minutes, and 150 mL of seed culture solution per vat was inoculated for 14 days at 25 ° C. The culture was stationary.

(Culture Example 2)
80 mL of the above seed medium was dispensed and PF1451 strain was inoculated into a 500 mL Erlenmeyer flask sterilized at 121 ° C. for 20 minutes, followed by shaking culture at 25 ° C. for 3 days to obtain a seed culture solution. Next, 40 mL each of liquid production medium was dispensed and three 500 mL Erlenmeyer flasks sterilized at 121 ° C. for 20 minutes were inoculated with 0.8 mL seed culture solution per Erlenmeyer flask, and cultured with shaking at 25 ° C. for 7 days.

(Culture Example 3)
80 mL of the above seed medium was dispensed and PF1451 strain was inoculated into 100 500 mL Erlenmeyer flasks sterilized at 121 ° C. for 20 minutes, followed by shaking culture at 25 ° C. for 3 days to obtain a seed culture solution. Next, 4 kg of solid production medium is placed in 50 pairs of 4.5 L deep bats with stainless steel lids and sterilized at 121 ° C. for 20 minutes. Add 2 L of additive solution and 150 mL of seed culture solution per set of bats and stir well. Then, static culture was performed at 25 ° C. for 14 days. The additive solution is boric acid 0.0001%, copper sulfate 0.00002%, potassium iodide 0.00005%, ferric chloride 0.0002%, manganese sulfate 0.0001%, sodium molybdate 0.00004%, zinc sulfate 0.0001%, cobalt chloride 0.00002%, yeast An aqueous solution containing 4% extract was prepared and sterilized at 121 ° C. for 20 minutes.

[Purification and isolation of PF1451 substance-producing bacteria]
(1) Purification and isolation of PF1451A substance and PF1451B substance a) Add 32L of 66% acetone water to the culture obtained in Cultivation Example 1, and after stirring, filter to remove brown rice and bacterial cells, 50% acetone Washed with water. Acetone was distilled off from the resulting extract under reduced pressure to obtain 8.0 L of a concentrated solution. This concentrated solution was passed through Diaion HP-20 1.1L. After washing with 1.0 L of water, the solution was developed with 2.0 L of 10% methanol water, 2.0 L of 30% methanol water, 4.0 L of 50% methanol water, and 2.0 L of methanol. Of these developing solvents, 50% aqueous methanol was distilled off under reduced pressure to obtain an oily substance. Silica gel 50g (Wakogel C300, manufactured by Wako Pure Chemical Industries, Ltd.) is applied to the oily substance and placed on top of a silica gel column 150g (Wakogel C300, manufactured by Wako Pure Chemical Industries, Ltd.). First, 50% acetone-hexane, then acetone, Thereafter, 1.0 L each of 10% methanol-chloroform, 20% methanol-chloroform, 30% methanol-chloroform, 60% methanol-chloroform, 80% methanol-chloroform and methanol was developed as a solvent. Of these eluents, 30% methanol-chloroform, 60% methanol-chloroform, and 80% methanol-chloroform eluents were combined and the solvent was distilled off under reduced pressure to obtain an oily substance.

b) The oily substance obtained in a) above is placed on top of 200 g of ODS silica gel column (Cosmo Seal 75 C18-OPN, manufactured by Nacalai Tesque), 0.01% trifluoroacetic acid aqueous solution, 5% methanol-0.01% trifluoroacetic acid. Aqueous solution, 10% methanol-0.01% trifluoroacetic acid aqueous solution, 20% methanol-0.01% trifluoroacetic acid aqueous solution, 30% methanol-0.01% trifluoroacetic acid aqueous solution, 40% methanol-0.01% trifluoroacetic acid aqueous solution, 60% methanol- A 1.0% trifluoroacetic acid aqueous solution, 80% methanol-0.01% trifluoroacetic acid aqueous solution, and methanol were each developed in 1.0 L as a solvent. Of these developing solvents, 10% methanol-0.01% trifluoroacetic acid aqueous solution, 20% methanol-0.01% trifluoroacetic acid aqueous solution, and 30% methanol-0.01% trifluoroacetic acid aqueous solution were combined and concentrated to dryness. As a result, 1.3 g of an oily substance was obtained.

C) The oily substance obtained in b) above was placed on top of a 500 g Sephadex LH-20 column (Amersham Biosciences AB) and developed with methanol to obtain 483 mg of an oily substance.

d) The oily substance obtained in the above c) was subjected to HPLC (TSKgel-amide-80, 5 μm, φ20 mm × 250 mm, manufactured by Tosoh Corporation), and the flow rate was 10 ml / min from 90% acetonitrile aqueous solution to 60% acetonitrile gradient solvent. Development was performed using a PDA detector, and each active ingredient was concentrated to dryness to obtain 85.7 mg of oily substance (1) and 30.3 mg of oily substance (2).

E) The oily substance (1) obtained in c) above was placed on top of a 500 g Sephadex LH-20 column (Amersham Biosciences AB) and developed with methanol to obtain 24.9 mg of PF1451A substance.

F) The oily substance (2) obtained in c) above was placed on top of a Sephadex LH-20 column 500 g (Amersham Biosciences AB) and developed with methanol to obtain 16.4 mg of PF1451B substance.

<Physicochemical properties of PF1451A substance>
(1) Color and properties: colorless powder
(2) Molecular formula: C32H39N7O9Cl2
(3) Mass spectrum (HR-ESI-MS): Measured value 736.2259 (M + H) +, Calculated value 736.2285
(4) Specific rotation: [α] D24.5 = –1.05 ° (c = 1.0, MeOH)
(5) UV absorption spectrum λmaxnm (E% cm)
[MeOH]: 202 (497), 287 (130)
[0.1N HCl-MeOH]: 209 (378), 280 (120)
[0.1N NaOH-MeOH]: 210 (1601), 254 (164), 296 (135)
(6) Infrared absorption spectrum νmax cm-1 (KBr)
: 3328, 3073, 2991, 2875, 1672, 1641, 1623, 1543, 1507, 1457, 1429, 1377, 1341, 1313, 1291, 1202, 1177, 1138
(7) 1H-NMR spectrum (500MHz, CD3OD) δ (ppm): 1.01 (t, 3H), 1.58 (m, 1H), 1.61 (s, 3H), 1.70 (s, 3H), 2.21 (m, 1H ), 2.28 (m, 1H), 2.67 (s, 3H), 2.70 (m, 1H), 3.87 (br-s, 1H), 4.21 (m, 2H), 4.65 (d, 1H), 4.76 to 4.83 ( m, 2H), 4.92 (m, 2H), 5.17 (s, 1H), 5.33 (s, 1H), 6.76 (s, 1H), 7.26 (s, 1H), 7.48 (s, 1H), 7.73 (s , 1H), 8.08 (s, 1H)
(8) 13C-NMR spectrum (125 MHz, D2O + 0.1 mM KSCN) δ (ppm): 8.1, 20.0, 21.4, 32.6, 32.7, 35.7, 47.5, 56.5, 58.3, 60.4, 69.7, 70.8, 73.9, 86.6, 112.9 , 123.3, 123.3, 124.1, 124.9, 125.1, 126.0, 131.3, 131.6, 137.8, 140.6, 145.6, 149.4, 166.5, 167.3, 169.9, 170.0, 171.3
(9) Solubility: Soluble in methanol, ethanol, water and DMSO.

<Physicochemical properties of PF1451B substance>
(1) Color and properties: colorless powder
(2) Molecular formula: C32H41N7O11Cl2
(3) Mass spectrum (HR-ESI-MS): Measured value 770.2311 (M + H) +, calculated value 770.2309
(4) Specific rotation: [α] D26 = -1.95 ° (c = 0.92, MeOH)
(5) UV absorption spectrum λmaxnm (E% cm)
[MeOH]: 202 (480), 269 (110)
[0.1N HCl-MeOH]: 209 (398), 273 (109)
[0.1N NaOH-MeOH]: 212 (1767), 253 (179), 300 (113)
(6) Infrared absorption spectrum νmax cm-1 (KBr)
: 3429, 2975, 2944, 2857, 2355, 1671, 1634, 1541, 1457, 1441, 1385, 1326, 1303, 1202, 1186, 1137, 1064
(7) 1H-NMR spectrum (500MHz, CD3OD) δ (ppm): 0.92 (t, 3H), 0.98 (s, 3H), 1.51 (m, 1H), 1.59 (s, 3H), 2.11 (m, 1H ), 2.20 (m, 1H), 2.58 (m, 1H), 2.60 (s, 3H), 3.23 (m, 2H), 3.84 (d, 1H), 4.10 (m, 1H), 4.16 (m, 1H) , 4.51 (s, 1H), 4.58 (d, 1H), 4.71 (m, 2H), 5.21 (s, 1H), 6.67 (s, 1H), 7.17 (d, 1H), 7.39 (s, 1H), 7.65 (s, 1H), 8.06 (s, 1H)
(8) 13C-NMR spectrum (125MHz, D2O + 0.1mM KSCN) δ (ppm): 8.1, 21.2, 21.2, 32.5, 32.7, 35.8, 47.6, 56.5, 56.9, 60.2, 68.6, 69.5, 70.7, 73.8, 74.7 , 86.5, 123.1, 123.3, 124.0, 124.5, 125.4, 125.9, 131.2, 131.6, 137.7, 145.6, 149.2, 166.9, 167.3, 170.0, 171.1, 171.1
(9) Solubility: Soluble in methanol, ethanol, water and DMSO.

(2) Purification and isolation of PF1451A substance (alternative method)
a) 120 ml of acetone was added to the culture obtained in Culture Example 2, and after stirring, the cells were filtered to remove the cells and washed with 50% acetone water. Acetone was distilled off from the obtained extract under reduced pressure to obtain 100 ml of a concentrated solution. This concentrated solution was passed through 10 ml of Diaion HP-20. After washing with 50 ml of water, development was performed with 50 ml of 10% aqueous methanol, 50 ml of 30% aqueous methanol, 50 ml of 50% aqueous methanol, and 50 ml of methanol. Of these developing solvents, 50% aqueous methanol was distilled off under reduced pressure to obtain an oily substance. Silica gel 1g (Wakogel C300, manufactured by Wako Pure Chemical Industries, Ltd.) is applied to this oily substance and placed on top of a silica gel column 5g (Wakogel C300, manufactured by Wako Pure Chemical Industries, Ltd.). First, 50% acetone-hexane, then acetone, Below, 20 ml each of 10% methanol-chloroform, 20% methanol-chloroform, 30% methanol-chloroform, 60% methanol-chloroform, 80% methanol-chloroform and methanol was developed as a solvent. Of these eluents, 30% methanol-chloroform, 60% methanol-chloroform, and 80% methanol-chloroform eluents were combined and the solvent was distilled off under reduced pressure to obtain an oily substance.

b) The oily substance obtained in a) above is placed on top of 5 g of ODS silica gel column (Cosmo Seal 75 C18-OPN, manufactured by Nacalai Tesque), 0.01% aqueous trifluoroacetic acid solution, 5% methanol-0.01% trifluoroacetic acid. Aqueous solution, 10% methanol-0.01% trifluoroacetic acid aqueous solution, 20% methanol-0.01% trifluoroacetic acid aqueous solution, 30% methanol-0.01% trifluoroacetic acid aqueous solution, 40% methanol-0.01% trifluoroacetic acid aqueous solution, 60% methanol- Each 20 ml of 0.01% trifluoroacetic acid aqueous solution, 80% methanol-0.01% trifluoroacetic acid aqueous solution, and methanol was developed as a solvent. Of these developing solvents, 10% methanol-0.01% trifluoroacetic acid aqueous solution, 20% methanol-0.01% trifluoroacetic acid aqueous solution, and 30% methanol-0.01% trifluoroacetic acid aqueous solution were combined and concentrated to dryness. An oily substance was obtained.

C) The oily substance obtained in b) above was placed on top of a 10 g Sephadex LH-20 column (Amersham Biosciences AB) and developed with methanol to obtain an oily substance.

d) The oily substance obtained in the above c) is subjected to HPLC (TSKgel-amide-80, 3 μm, φ4.6 mm × 150 mm, manufactured by Tosoh Corporation), and the flow rate is 0.8 ml from 90% acetonitrile aqueous solution to 60% acetonitrile gradient solvent. Development was performed using a PDA detector / min, and the active ingredient was concentrated to dryness to obtain 0.2 mg of PF1451A substance.

(3) Purification and isolation of PF1451C, PF1451D, and PF1451a a) Add 200L of 70% methanol water to 200kg of the culture obtained in Culture Example 3, and filter after filtration to remove brown rice and bacterial cells. The extract was washed with methanol water to obtain 675 L of an extract. Methanol was distilled off from the obtained extract under reduced pressure to obtain 90 L of a concentrated solution. 100 L of ethyl acetate was added to this concentrated solution, and after stirring, the ethyl acetate layer was removed, and the remaining 90 L of the aqueous layer was further concentrated to 85 L under reduced pressure. The obtained concentrated liquid was passed through Diaion HP-20 20L. Development was performed with 60 L of 10% methanol water, 60 L of 70% methanol water, and 60 L of methanol. Among these developing solvents, 70% methanol aqueous fraction was distilled off under reduced pressure to obtain 1 L of concentrated liquid.

B) 500 g of ODS silica gel (Cosmo Seal 75 C18-OPN, manufactured by Nacalai Tesque) was applied to the concentrate obtained in a) above. This is placed on the top of 1.5 kg of ODS silica gel column, 0.05% trifluoroacetic acid aqueous solution, 5% methanol-0.05% trifluoroacetic acid aqueous solution, 10% methanol-0.05% trifluoroacetic acid aqueous solution-1, 10% methanol-0.05% trichome. Fluoroacetic acid aqueous solution-2, 20% methanol-0.05% trifluoroacetic acid aqueous solution-1, 20% methanol-0.05% trifluoroacetic acid aqueous solution-2, 30% methanol-0.05% trifluoroacetic acid aqueous solution, 60% methanol-0.05% tri 4 L each of an aqueous fluoroacetic acid solution and methanol were developed as solvents. Of these developing solvents, the fractions of 10% methanol-0.05% trifluoroacetic acid aqueous solution-1, 10% methanol-0.05% trifluoroacetic acid aqueous solution-2, 20% methanol-0.05% trifluoroacetic acid aqueous solution-1 are combined. The product was concentrated to dryness to obtain 73.4 g of an oily substance.

C) The oily substance obtained in b) above was placed on top of Sephadex LH-20 column 8.5L (Amersham Biosciences AB) and developed with methanol to obtain an oily substance.

D) The above operation c) was repeated 3 times to obtain 19 g of an oily substance.

e) 300 mg of the oily substance obtained in d) above was subjected to HPLC (TSKgel-amide-80, 5 μm, φ20 mm × 250 mm, manufactured by Tosoh Corporation), and a flow rate of 10 ml / min from 93% acetonitrile aqueous solution to 85% acetonitrile aqueous solution gradient solvent. min, developed using a PDA detector, and concentrated each active ingredient to dryness to obtain 1.8 g of oily substance mainly composed of PF1451A, 389 mg of oily substance (1) and 1.1 g of oily substance (2) .

f) The oily substance (1) obtained in e) above was subjected to HPLC (TSKgel-amide-80, 5 μm, φ20 mm × 250 mm, manufactured by Tosoh Corporation), and the flow rate was changed from 94% acetonitrile aqueous solution to 88% acetonitrile aqueous solution gradient solvent. Development was performed using a PDA detector at 10 ml / min, and the active ingredient was concentrated and dried to obtain 153 mg of an oily substance.

G) After adding 5 ml of n-butanol and 5 ml of water to the oily substance obtained in f) above and stirring, the n-butanol layer was concentrated to dryness to obtain 123 mg of PF1451C substance.

h) The oily substance (2) obtained in e) above was subjected to HPLC (TSKgel-amide-80, 5 μm, φ20 mm × 250 mm, manufactured by Tosoh Corporation), and the flow rate was changed from 93% acetonitrile aqueous solution to 90% acetonitrile aqueous solution gradient solvent. Development was performed using a PDA detector at 10 ml / min, and each active ingredient was concentrated and dried to obtain 170 mg of oily substance (3) and 96 mg of oily substance (4).

I) The oily substance (3) obtained in h) above was placed on top of a Sephadex LH-20 column 700 ml (Amersham Biosciences AB) and developed with methanol to obtain an oily substance. After adding 5 ml of n-butanol and 5 ml of water to this, the n-butanol layer was concentrated to dryness to obtain 44 mg of an oily substance.

j) The oily substance obtained in i) above was subjected to HPLC (TSKgel-amide-80, 5 μm, φ20 mm × 250 mm, manufactured by Tosoh Corporation), and the flow rate was 10 ml / min with a gradient solvent from 92% acetonitrile aqueous solution to 90% acetonitrile aqueous solution. The active ingredient was concentrated and dried to obtain 10.1 mg of PF1451D substance.

K) After adding 5 ml of n-butanol and 5 ml of water to the oily substance (4) obtained in h) above and stirring, the n-butanol layer was concentrated to dryness to obtain 38 mg of PF1451E substance.

<Physicochemical properties of PF1451C substance>
(1) Color and properties: colorless powder
(2) Molecular formula: C32H39N7O8Cl2
(3) Mass spectrum (HR-ESI-MS): Measured value 720.2304 (M + H) +, calculated value 720.2315
(4) 1H-NMR spectrum (500 MHz, CD3OD) δ (ppm): 1.06 (t, 3H), 1.60 (s, 3H), 1.70 (s, 3H), 2.29 (m, 1H), 2.64 (m, 1H ), 2.69 (s, 3H), 2.87 (dd, 1H), 3.22 (dd, 1H), 4.03 (m, 1H), 4.18 (m, 2H), 4.78 (m, 1H), 4.81 (m, 1H) , 4.99 (s, 1H), 5.03 (s, 1H), 5.23 (s, 1H), 5.39 (s, 1H), 6.72 (s, 1H), 7.00 (s, 1H), 7.27 (s, 1H), 7.46 (s, 1H), 8.01 (s, 1H) 8.92 (s, 1H)
(5) 13C-NMR spectrum (125 MHz, CD3OD) δ (ppm): 8.1, 20.0, 20.1, 32.7, 32.8, 35.7, 36.4, 47.4, 57.5, 58.6, 60.3, 63.8, 70.8, 86.4, 113.1, 120.6, 122.7 , 123.3, 123.7, 126.0, 126.3, 126.7, 128.9, 136.3, 140.7, 146.5, 148.7, 166.0, 167.6, 170.0, 170.5, 171.2
(6) Solubility: Soluble in methanol, ethanol, water and DMSO.

<Physicochemical properties of PF1451D substance>
(1) Color and properties: colorless powder
(2) Molecular formula: C32H40N7O9Cl
(3) Mass spectrum (HR-ESI-MS): Measured value 702.2655 (M + H) +, Calculated value 702.2654
(4) 1H-NMR spectrum (500 MHz, CD3OD) δ (ppm): 1.02 (t, 3H), 1.57 (m, 1H), 1.63 (s, 3H), 1.64 (s, 3H), 2.00 (m, 1H ), 2.15 (m, 2H), 2.28 (m, 1H), 2.32 (m, 1H), 2.66 (s, 3H), 3.83 (d, 1H), 3.94 (m, 1H), 4.08 (m, 1H) , 4.51 (dd, 1H), 4.66 (d, 1H), 4.92 (m, 2H), 5.13 (s, 1H), 5.21 (s, 1H), 6.80 (s, 1H), 7.28 (s, 1H), 7.48 (s, 1H), 8.00 (s, 1H) 8.86 (s, 1H)
(5) 13C-NMR spectrum (125 MHz, CD3OD) δ (ppm): 8.2, 19.9, 21.5, 26.1, 30.5, 32.1, 32.5, 50.9, 56.8, 58.5, 62.0, 69.5, 73.7, 86.7, 113.4, 120.6, 123.3 , 123.3, 123.4, 124.1, 124.5, 129.0, 131.9, 136.5, 140.7, 145.6, 149.2, 166.3, 166.5, 170.2, 170.6, 173.6
(6) Solubility: Soluble in methanol, ethanol, water and DMSO.

<Physicochemical properties of PF1451E material>
(1) Color and properties: colorless powder
(2) Molecular formula: C31H37N7O9Cl2
(3) Mass spectrum (HR-ESI-MS): Measured value 722.2103 (M + H) +, calculated value 722.2113
(4) 1H-NMR spectrum (500MHz, CD3OD) δ (ppm): 1.03 (t, 3H), 1.59 (m, 1H), 1.62 (s, 3H), 1.68 (s, 3H), 2.20 (m, 1H ), 2.29 (m, 1H), 2.66 (m, 1H), 3.87 (d, 1H), 4.19 (m, 2H), 4.62 (d, 1H), 4.77 (m, 1H), 4.80 (m, 1H) , 4.96 (m, 2H), 5.09 (s, 1H), 5.32 (s, 1H), 6.81 (s, 1H), 7.27 (s, 1H), 7.47 (s, 1H), 7.94 (s, 1H) 8.70 (s, 1H)
(5) 13C-NMR spectrum (125 MHz, CD3OD) δ (ppm): 8.1, 19.9, 21.3, 32.5, 35.7, 47.5, 56.5, 58.3, 60.3, 61.0, 70.7, 74.2, 86.5, 113.1, 121.2, 123.2, 123.4 , 123.5, 124.0, 124.5, 129.5, 131.9, 136.5, 140.7, 145.6, 149.2, 166.2, 167.7, 170.1, 170.3, 171.2
(6) Solubility: Soluble in methanol, ethanol, water and DMSO.

(Production Example 2)
A PF1451A substance, a PF1451B substance, a PF1451C substance, a PF1451D substance, and a PF1451E substance were obtained in the same manner as in Production Example 1 except that the PF1458 strain was used instead of the PF1451 strain as the PF1451 substance-producing bacterium.

(Production Example 3)
200 μl of 0.1N hydrochloric acid (1 drop) and trimethylsilyldiazomethane (10% hexane solution) were repeatedly added to a methanol solution (1 ml) of 30 mg of the PF1451A substance obtained in (1) of Production Example 1 and stirred until the raw material disappeared. . The methanol layer was concentrated to dryness, and the residue was subjected to HPLC (Inertsil ODS-2, φ20mmx250mm, manufactured by GL Sciences Inc.). Gradient from 18% acetonitrile-0.1% trifluoroacetic acid aqueous solution to 30% acetonitrile-0.1% trifluoroacetic acid aqueous solution Development using a PDA detector with a flow rate of 8 ml / min in the system solvent, and the following formula:

2 mg of PF1451A-1 represented by the following formula:

9 mg of the PF1451A-2 substance represented by the formula:

<Physicochemical properties of PF1451A-1 substance>
(1) Color and properties: colorless powder
(2) Molecular formula: C35H45N7O9Cl2
(3) Mass spectrum (ESI-MS): 778 (M + H) ⁺
(4) 1H-NMR spectrum (500MHz, CD3OD) δ (ppm): 1.06 (t, 3H), 1.54 (m, 1H), 1.60 (s, 3H), 1.72 (s, 3H), 2.23 (m, 1H ), 2.31 (m, 1H), 2.63 (m, 1H), 3.44 (s, 9H), 3.85 (s, 3H), 4.14 (d, 1H), 4.23 (m, 2H), 4.76 (m, 2H) , 4.91 (m, 2H), 5.14 (m, 2H), 5.35 (m, 1H), 6.75 (br-s, 1H), 7.29 (br-s, 1H), 7.42 (s, 1H), 8.01 (s , 1H), 8.86 (s, 1H)
(5) Solubility: Soluble in methanol, ethanol, water and DMSO.

<Physicochemical properties of PF1451A-2 substance>
(1) Color and properties: colorless powder
(2) Molecular formula: C36H47N7O9Cl2
(3) Mass spectrum (ESI-MS): 792 (M + H) ⁺
(4) 1H-NMR spectrum (500MHz, CD3OD) δ (ppm): 1.02 (t, 3H), 1.51 (s, 3H), 1.53 (m, 1H), 1.66 (s, 3H), 2.02 (m, 1H ), 2.23 (m, 1H), 2.56 (m, 1H), 3.36 (s, 9H), 3.75 (s, 3H), 3.77 (s, 3H), 4.03 (m, 1H), 4.09 (d, 1H) , 4.16 (m, 1H), 4.67 (m, 2H), 4.83 (m, 2H), 5.05 (s, 1H), 5.11 (d, 1H), 5.27 (s, 1H), 6.74 (s, 1H), 7.29 (s, 1H), 7.83 (s, 1H), 7.96 (s, 1H), 8.88 (s, 1H)
(5) 13C-NMR spectrum (125 MHz, CD3OD) δ (ppm): 7.9, 20.0, 20.5, 32.9, 35.6, 47.6, 53.5, 54.8, 54.8, 54.8, 55.6, 57.4, 60.2, 61.2, 70.5, 73.4, 79.4 , 87.2, 112.6, 120.4, 122.6, 122.9, 125.0, 125.5, 128.6, 131.4, 136.4, 136.9, 140.5, 151.0, 152.6, 165.1, 165.8, 169.8, 170.1, 171.1
(6) Solubility: Soluble in methanol, ethanol, water and DMSO.

(Formulation example)
Formulation Example 1 [Granule]
5% by weight of the compound of the present invention
Bentonite 40% by weight
Talc 10% by weight
43% by weight of clay
2% by weight calcium lignin sulfonate
The above components were pulverized and mixed uniformly, kneaded well with water, and granulated and dried to obtain granules.

Formulation Example 2 [Wetting Agent]
Compound of the present invention 30% by weight
50% by weight of clay
2% white carbon
Diatomaceous earth 13% by weight
Calcium lignin sulfonate 4% by weight
Sodium lauryl sulfate 1% by weight
The above ingredients were mixed uniformly and pulverized to obtain a wettable powder.

Formulation Example 3 [Granule wettable powder]
Compound of the present invention 30% by weight
60% clay
Dextrin 5% by weight
Alkyl maleic acid copolymer 4% by weight
Sodium lauryl sulfate 1% by weight
The above components were uniformly pulverized and mixed, water was added and kneaded well, and then granulated and dried to obtain a granular wettable powder.

Formulation Example 4 [Flowable Agent]
Compound of the present invention 25% by weight
POE polystyryl phenyl ether sulfate 5% by weight
Propylene glycol 6% by weight
Bentonite 1% by weight
Xanthan gum 1% aqueous solution 3% by weight
PRONAL EX-300 (Toho Chemical Industry Co., Ltd.) 0.05% by weight
ADDAC 827 (Kay Kasei Co., Ltd.) 0.02% by weight
100% by weight with water
The total amount excluding xanthan gum 1% aqueous solution and an appropriate amount of water from the above blend was premixed and then pulverized with a wet pulverizer. Thereafter, a 1% aqueous solution of xanthan gum and the remaining water were added to obtain a flowable agent at 100% by weight.

Formulation Example 5 [Emulsion]
The compound of the present invention 15% by weight
N, N-dimethylformamide 20% by weight
Solvesso 150 (ExxonMobil Co., Ltd.) 55% by weight
10% by weight of polyoxyethylene alkyl aryl ether
The above ingredients were uniformly mixed and dissolved to obtain an emulsion.

Formulation Example 6 [Emulsion]
The compound of the present invention 15% by weight
Solvesso 150 (ExxonMobil Co., Ltd.) 50% by weight
10% by weight of polyoxyethylene alkyl aryl ether
Calcium alkylbenzenesulfonate 5% by weight
N-methyl-2-pyrrolidone 20% by weight
The above ingredients were uniformly mixed and dissolved to obtain an emulsion.

Formulation Example 7 [Dust]
2% by weight of the compound of the present invention
60% clay
Talc 37% by weight
Calcium stearate 1% by weight
The said component was mixed uniformly and the powder agent was obtained.

Formulation Example 8 [DL powder]
2% by weight of the compound of the present invention
DL clay 94.5% by weight
2% white carbon
Calcium stearate 1% by weight
Light liquid paraffin 0.5% by weight
The said component was mixed uniformly and the powder agent was obtained.

Formulation Example 9 [Fine Granule F]
2% by weight of the compound of the present invention
Carrier 94% by weight
2% white carbon
Hyzol SAS-296 2% by weight
The said component was mixed uniformly and the powder agent was obtained.

(Test example)
(Test Example 1) Effect on Tomato Blight The PF1451A substance, PF1451B substance, PF1421C substance, PF1451D substance or PF1451E substance obtained in Production Example 1 was dissolved in methanol to prepare a 1 mg / mL solution. This was diluted with deionized water so as to be 0.1 mg / mL, and neoesterin was added as a spreading agent so as to have a dilution factor of 3000 to obtain a spray solution. A sufficient amount of spray solution was sprayed on tomatoes (variety: Tiny Tim) 16 days after sowing grown in a 3 cm plastic cup. Zoosporangium suspension of tomato late blight fungus, prepared spraying next day 10 ⁴ / mL (Phytophthora infestans) was sprayed and inoculated and allowed to stand for 24 hours in a moist chamber of 21 ° C.. Thereafter, it was controlled in a greenhouse, and after 4 days after inoculation, the true leaf disease intensity was visually determined according to the following criteria, and then the control value was calculated using the following formula 1 and the following formula 2.
[Strength of disease]
0: No disease is observed 1: Disease area rate is less than 20% 2: Disease area rate is 20% or more and less than 40% 3: Disease area rate is 40% or more and less than 60% 4: Disease area rate is 60% or more and 80% Less than 5: Disease area ratio is 80% or more Formula 1: Disease severity = Average value of disease intensity / 5 × 100
Formula 2: Control value = (Disease level of untreated group-Disease level of treated group) / Disease level of untreated group x 100
In this test, the PF1451A substance, the PF1451B substance, the PF1421C substance, the PF1451D substance, and the PF1451E substance all showed a control value of 90 or more.

(Test Example 2) Effect on Tomato Blight The PF1451A substance obtained in Production Example 1 was dissolved in methanol to prepare a 1 mg / mL solution. This was diluted with deionized water to 0.1 mg / mL. The soil of tomato (variety: Tiny Tim) 16 days after sowing cultivated in the pot was washed away, and the root was immersed in a diluted solution of PF1451A substance for 1 hour. Then, 3 cm were transplanted in plastic cups, the zoosporangia suspension of tomato late blight fungus, prepared after 1 day ported to 10 ⁴ / mL (Phytophthora infestans) was inoculated by spraying, 24 hours allowed to stand in a moist chamber of 21 ° C. did. Thereafter, the plants were managed in a greenhouse, and after 4 days after inoculation, the intensity of disease on the true leaf was visually determined according to the following criteria, and then the control value was calculated using the following formula 3 and formula 4.
[Strength of disease]
0: No disease is observed 1: Disease area rate is less than 20% 2: Disease area rate is 20% or more and less than 40% 3: Disease area rate is 40% or more and less than 60% 4: Disease area rate is 60% or more and 80% Less than 5: Disease area ratio is 80% or more Formula 3: Disease severity = Average value of disease intensity / 5 × 100
Formula 4: Control value = (Disease level in untreated area-Disease level in treated area) / Disease degree in untreated area x 100
In this test, the PF1451A substance showed a control value of 90 or more.

(Test Example 3) Effect on Potato Plague Disease The PF1451A substance obtained in Production Example 1 was dissolved in methanol to prepare a 1 mg / mL solution. This was diluted with deionized water so as to be 0.1 mg / mL, and neoesterin was added as a spreading agent so as to obtain a dilution factor of 5000 times to obtain a spray solution. A sufficient amount of spray solution was sprayed on a potato (cultivar: Baron potato) with a height of 25 cm grown in a 20 cm pot. Zoosporangium suspension of potato Phytophthora infestans prepared in spraying following day 10 ⁴ / mL (Phytophthora infestans) was sprayed and inoculated and allowed to stand for 24 hours in a moist chamber of 21 ° C.. Then, after controlling in a greenhouse and visually inspecting the intensity of disease for each leaf position according to the following criteria 5 days after inoculation, the control value was calculated using the following formula 5 and the following formula 6.
[Strength of disease]
0: No disease is observed 1: Disease area rate is less than 20% 2: Disease area rate is 20% or more and less than 40% 3: Disease area rate is 40% or more and less than 60% 4: Disease area rate is 60% or more and 80% Less than 5: Disease area ratio is 80% or more Formula 5: Disease severity = average value of disease intensity / 5 × 100
Formula 6: Control value = (Disease level of untreated group-Disease level of treated group) / Disease level of untreated group x 100
In this test, the PF1451A substance showed a control value of 90 or more.

(Test Example 4) Effect on Radish White Rust Disease The PF1451A substance obtained in Production Example 1 was dissolved in methanol to prepare a 1 mg / mL solution. This was diluted with deionized water to a concentration of 0.1 mg / mL to obtain a spray solution. A sufficient amount of spray solution was sprayed on radish (variety: radish) 21 days after sowing grown in a 5 cm pot. The zoosporangia suspension of air drying after 10 ⁴ cells / mL in the prepared radish white rust (Albugo macrospora) was sprayed and inoculated and allowed to stand for 24 hours in a moist chamber of 21 ° C.. Thereafter, it was controlled in a greenhouse, and the number of lesions formed on the true leaf was counted 9 days after inoculation, and the control value was calculated using the following formula 7.
Formula 7: Control value = (Average number of lesions per untreated strain-average number of lesions per treated strain) / Average number of lesions per untreated strain × 100
In this test, the PF1451A substance showed a control value of 90 or more.

(Test Example 5) Effect on Cucumber downy mildew The PF1451A substance obtained in Production Example 1 was dissolved in methanol to prepare a 2 mg / mL solution. This was diluted with deionized water to 0.2 mg / mL, and neoesterin was added as a spreading agent to a dilution ratio of 3000 times to obtain a spray solution. A sufficient amount of spray solution was sprayed on cucumbers 14 days after sowing grown in 3 cm pots. The zoosporangia suspension of cucumber downy prepared in 10 ⁴ cells / mL after air drying and mildew (Pseudoperonospora cubensis) was inoculated by spraying, and allowed to stand for 24 hours in a moist chamber of 21 ° C.. Then, after controlling in a greenhouse and visually inspecting the intensity of the first true leaf disease on the 8th day after inoculation, the control value was calculated using the following formula 8 and the following formula 9.
[Strength of disease]
0: No disease is observed 1: Disease area ratio is less than 5% 2: Disease area ratio is 5% or more and less than 20% 3: Disease area ratio is 20% or more and less than 40% 4: Disease area ratio is 40% or more and 60% Less than 5: Disease area ratio is 60% or more and less than 80% 6: Disease area ratio is 80% or more Formula 8: Disease severity = average value of disease intensity / 6 × 100
Formula 9: Control value = (Disease level of untreated area-Disease level of treated area) / Disease degree of untreated area x 100
In this test, the PF1451A substance showed a control value of 90 or more.

(Test Example 6) Growth inhibitory activity against rice seedling blight fungus Rice seedling blight fungus (Pythium graminicola) was subjected to shaking culture at 25 ° C for 5 days using Potato Sucrose Broth (PSB). This was ground with Hiscotron and diluted 100 times with fresh PSB to make a bacterial solution. The PF1451A material was dissolved in dimethyl sulfoxide to prepare a 12.8 mg / mL solution. 0.8 μL of the solution and 160 μL of the bacterial solution were mixed so that the final concentration of the PF1451A substance obtained in Production Example 1 was 64 mg / L, and cultured at 25 ° C. for 3 days. As a result of observing the elongation of the mycelium, the mycelium was not elongated in the medium containing the PF1451A substance.

(Test Example 7) Effect on Wheat Red Rust Disease The PF1451A substance obtained in Production Example 1 was dissolved in methanol to prepare a 2 mg / mL solution. This was diluted with deionized water so as to be 0.2 mg / mL, and neoesterin was added as a spreading agent so as to have a dilution factor of 1000 to obtain a spray solution. A sufficient amount of spray solution was sprayed on the three-leaf wheat (cultivar: Norin 61) grown in a 3cm pot. After air-drying, a spore suspension of wheat rust (Puccinia recondita) prepared to 3 × 10 ⁵ cells / mL was spray-inoculated and left in a wet chamber at 25 ° C. for 24 hours. Thereafter, it was controlled in a greenhouse, and the number of lesions formed on the second leaf was counted 8 days after inoculation, and the control value was calculated using the following formula 10.
Formula 10: Control value = (Average number of lesions per untreated strain-average number of lesions per untreated strain) / Average number of lesions per untreated strain × 100
In this test, the PF1451A substance exhibited a control value of 80 or more.

(Test Example 8) Effect on grape downy mildew The PF1451A substance obtained in Production Example 1 was dissolved in methanol to prepare a 2 mg / mL solution. This was diluted with deionized water to a concentration of 0.2 mg / mL to obtain a spray solution. 0.02 mL of spray solution was sprayed on a leaf disk obtained by hollowing out the leaves of grapes (variety: Kaiji) with a cork borer with a diameter of 14 mm. After air-drying, spray inoculate the zoosporangium suspension of grape mildew fungus (Plasmopara viticola) prepared to 10 ⁵ cells / mL, and after 7 days of inoculation, visually evaluate the severity of the disease according to the following criteria, then The control value was calculated using Formula 11 and Formula 12 below.
[Strength of disease]
0: No disease is observed 1: The lesion area ratio is less than 33% 2: The lesion area ratio is 33% or more and less than 67% 3: The lesion area ratio is 67% or more Formula 11: Disease severity = severity of disease Average value / 3 × 100
Formula 12: Control value = (Disease level of untreated group-Disease level of treated group) / Disease level of untreated group x 100
In this test, the PF1451A substance showed a control value of 90 or more.

(Test Example 9) Growth inhibitory activity against gray mold fungus Gray mold fungus (Botrytis cinerea) was cultured with shaking at 21 ° C for 5 days using Potato Sucrose Broth (PSB). This was ground with Hiscotron and diluted 100 times with fresh PSB to make a bacterial solution. A PF1451A substance, a PF1451C substance or a PF1451D substance was dissolved in dimethyl sulfoxide to prepare a 12.8 mg / mL solution. 0.8 μL of the solution and 160 μL of the bacterial solution were mixed so that the final concentration of the PF1451A substance, the PF1451C substance, or the PF1451D substance obtained in Production Example 1 was 64 mg / L, and cultured at 25 ° C. for 3 days. As a result of observing mycelial elongation, inhibition of mycelial elongation was observed in all the media containing the PF1451A substance, the PF1451C substance, and the PF1451D substance.
(Test Example 10) Growth Inhibitory Activity against Rice Blast Fungus Rice blast fungus (Pyricularia oryzae) was cultured with shaking at 21 ° C for 5 days using Potato Sucrose Broth (PSB). This was ground with Hiscotron and diluted 100 times with fresh PSB to make a bacterial solution. The PF1451A substance, PF1451C substance or PF1451D substance obtained in Production Example 1 was dissolved in dimethyl sulfoxide to prepare a 12.8 mg / mL solution. 0.8 μL of the solution and 160 μL of the bacterial solution were mixed so that the final concentration of the PF1451A substance, the PF1451C substance, or the PF1451D substance was 64 mg / L, and cultured at 25 ° C. for 3 days. As a result of observing mycelial elongation, inhibition of mycelial elongation was observed in all the media containing the PF1451A substance, the PF1451C substance, and the PF1451D substance.

The novel compound of the present invention is useful as an active ingredient of a novel fungicide against pests.

1.
(1) Identification display: PF1451
(2) Receipt number: NITE ABP-01785
(3) Date of receipt (date of domestic deposit): December 25, 2013 (Date of request for transfer to international deposit: July 23, 2015)
(4) Depositary institution: National Institute for Product Evaluation Technology Patent Microorganism Depositary Center
(1) Identification display: PF1458
(2) Receipt number: NITE ABP-02091
(3) Date of receipt: July 23, 2015 (4) Depositary institution: National Institute for Product Evaluation Technology Patent Microorganism Depositary Center

[Supplement under Rule 26 16.09.2015]

Claims (9)

1. A compound represented by the following formula (1) and an agricultural and horticulturally acceptable salt thereof.
   

   

   [In the formula (1), R ₁ represents an isopropenyl group or a 1,2-dihydroxypropan-2-yl group, R ₂ represents a hydrogen atom or a hydroxyl group, R ₃ represents a hydrogen atom or a chlorine atom, R ₄ represents an amino group, a methylamino group, or a trimethylamino group, R ₅ represents a hydroxyl group or a hydroxymethyl group, and R ₆ represents a hydrogen atom or a methyl group. ]
2. An agricultural and horticultural fungicide containing at least one compound selected from the group consisting of the compound represented by the formula (1) according to claim 1 and an agriculturally and horticulturally acceptable salt thereof.
3. A method for producing at least one compound selected from the group consisting of the compound represented by the formula (1) according to claim 1 and a salt that is agriculturally and horticultically acceptable,
   From the compound represented by the following formula (2), the compound represented by the following formula (3), the compound represented by the following formula (4), the compound represented by the following formula (5) and the compound represented by the following formula (6) Culturing a strain having the ability to produce at least one compound selected from the group consisting of:
   From the culture, the compound represented by the formula (2), the compound represented by the formula (3), the compound represented by the formula (4), the compound represented by the formula (5), or the formula (6) And the step of isolating the compound represented by formula (1) to obtain the compound represented by the formula (1) or an agricultural and horticulturally acceptable salt thereof;
   The manufacturing method of the compound containing this.
   

   

   

   

   

   
4. The method for producing a compound according to claim 3, wherein the strain is a microorganism belonging to the genus Taralomyces or Penicillium.
5. The aforementioned strain is a strain whose receipt number is NITE ABP-01785 at the National Institute of Technology and Evaluation of the National Institute of Technology and Evaluation, and its mutant strain, The method for producing a compound according to claim 3 or 4, which is at least one selected from the group consisting of a strain of NITE ABP-02091 and a mutant thereof.
6. A strain belonging to the genus Talaromyces, a strain whose receipt number is NITE ABP-01785 in the National Institute of Technology and Evaluation of the National Institute of Technology and Evaluation, or a mutant thereof, and a compound represented by the following formula (2): At least one selected from the group consisting of a compound represented by the following formula (3), a compound represented by the following formula (4), a compound represented by the following formula (5) and a compound represented by the following formula (6): A mutant strain capable of producing a compound.
   

   

   

   

   

   
7. A strain belonging to the genus Penicillium, a strain having an acceptance number of NITE ABP-02091 at the National Institute of Technology and Evaluation of the National Institute of Technology and Evaluation, or a mutant thereof, and a compound represented by the following formula (2): At least one selected from the group consisting of a compound represented by the following formula (3), a compound represented by the following formula (4), a compound represented by the following formula (5) and a compound represented by the following formula (6): A mutant strain capable of producing a compound.
   

   

   

   

   

   
8. The at least 1 sort (s) of compound selected from the group which consists of the compound represented by said Formula (1) of Claim 1, and its agriculturally and horticulturally acceptable salt, or the agricultural and horticultural fungicide of Claim 2 A method for controlling plant diseases using
9. The sterilization for agricultural or horticultural use according to claim 2, or at least one compound selected from the group consisting of the compound represented by the formula (1) according to claim 1 and a salt that is acceptable for agricultural and horticultural purposes. A method of protecting a plant from plant diseases using an agent.