JP2017165655A - Novel bactericide for agricultural and horticultural use, pf1451 material, and method for producing the same - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a novel bactericide for agricultural and horticultural use having bactericidal activity for agricultural and horticultural use, a compound used as an active ingredient thereof and a method for producing the same.SOLUTION: The present invention provides PF1451A material discovered in a culture medium of a Penicillium microorganism, Penicillium sp. PF1451 strain NITE P-01785, having a novel chemical structure and represented by formula (1), and PF1451B material of a similar structure, or a bactericide for agricultural and horticultural use comprising them, and a method for producing them by microorganism culture.SELECTED DRAWING: None

Description

  The present invention relates to a novel PF1451 substance, an agricultural and horticultural fungicide containing the compound as an active ingredient, and a method for producing the compound.

Many agricultural and horticultural fungicides have been found so far, but new drugs are still required due to increased drug resistance.
It has been reported that a compound called homopsin A having the same partial structure as the substance of the present invention has anticancer activity (Patent Document 1, Non-Patent Documents 1 and 2). However, it is not described that this compound can be used as an agricultural and horticultural fungicide.

WO2001 / 022986 Publication

Toxicon, 21, (Suppl. 3), 1983, 149 Tetrahedron, 1989,45,8,2351

  Many agricultural and horticultural fungicides have been found so far, but new drugs are still required due to increased drug resistance.

  An object of this invention is to provide the compound utilized as an active ingredient of the novel agricultural and horticultural fungicide, and its manufacturing method.

  As a result of earnest search research to find a compound having the above properties, the present inventors have found a compound having an excellent control effect against phytopathogenic fungi in a fungal culture solution, and these active substances. And a PF1451A substance and a PF1451B substance having novel chemical structures represented by the following formulas (1) and (2) were found, and the present invention was completed.

  That is, the present inventors provide, as a first invention, a PF1451A substance represented by the following formula (1), a PF1451B substance represented by the following formula (2), or an agricultural and horticulturally acceptable salt thereof. .

式（１）

Formula (1)

式（２）

Formula (2)

  As a second invention, the sterilization for agricultural and horticultural use comprising at least one PF1451A substance represented by the above formula (1), PF1451B substance represented by the above formula (2) or an agriculturally and horticulturally acceptable salt thereof. Provide the agent.

  As a third invention, a microorganism belonging to the genus Penicillium and capable of producing a PF1451A substance or a PF1451B substance is cultured, and the PF1451A substance represented by the formula (1) or the formula (2) is cultured from the culture. PF1451B substance represented by formula (I) is isolated, and a method for producing the PF1451B substance is provided.

  As a fourth invention, the PF1451A substance represented by the above formula (1), the PF1451B substance represented by the above formula (2) or their horticulture-acceptable salts, and the PF1451A substance, PF1451B substance or their agriculture Provided is a method for controlling plant diseases using an agricultural and horticultural fungicide comprising one or more horticulturally acceptable salts.

  The novel substance PF1451A substance, PF1451B substance or their agriculturally and horticulturally acceptable salts of the present invention are useful as active ingredients for agricultural and horticultural fungicides.

  In the present invention, the PF1451A substance represented by the formula (1) or the PF1451B substance represented by the formula (2) is obtained by culturing a PF1451A substance or a PF1451B substance-producing bacterium, and PF1451A substance or PF1451B from the culture. It can be produced by purifying and isolating the material. Hereinafter, the PF1451A substance and the PF1451B substance may be collectively referred to as a PF1451 substance.

  Examples of salts that are acceptable in agriculture and horticulture include, for example, alkali metal salts such as sodium and potassium, alkaline earth metal salts such as calcium and barium, and salts with inorganic acids such as hydrochloric acid, sulfuric acid, nitric acid, and phosphoric acid, or Examples thereof include salts with organic acids such as acetic acid, citric acid and benzoic acid.

  Examples of the PF1451 substance-producing bacteria include the PF1451 strain which is a filamentous fungus isolated by the present inventors from the soil of Fukuoka Prefecture and belongs to the genus Penicillium, Penicillium sp. PF1451 NITE P-01785. The bacteriological properties, culture method and purification method of PF1451 substance of this strain are as follows.

Note that the PF1451 substance-producing bacterium is not limited to the specific microorganism described in the present specification. Any bacterium may be used as long as it has the ability to produce the PF1451A substance or the PF1451B substance.
Examples of microorganisms that can be used include Penicillium sp. PF1451, its passages, artificial mutants, natural mutants, and genetically modified strains.

  The taxonomic properties, culture method and purification method and isolation of the PF1451A substance represented by the formula (1) or the PF1451B substance represented by the formula (2) are as follows.

[Taxonomy of PF1451 strain]
The mycological properties of PF1451 strain are as follows.

(A) Characteristics of culture
The growth of the Penicillium sp. PF1451 strain after 3 weeks of culture at 25 ° C, and the diameter, surface properties, and color of the colony are as follows. The description of colony color tone was based on Kornerup and Wanscher (1978). In addition, soluble pigment was not observed in all media.
Potato dextrose agar: good growth, colony diameter 60-70mm, surface texture velvety, color tone 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 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) Morphological features
Penicillium sp. 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 under a microscope.
The vegetative mycelium is formed on or in the surface of the agar 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. The formation of penicillus is observed 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 form from phialide, and are spherical to subspherical, colorless to light brown, 1 cell, and the surface is finely spiny.
The presence or absence of reproductive organs is not observed from culture specimens cultured for about 4 weeks.
From the results of colony properties and morphological observation, it was called Penicillium sp. PF1451 belonging to the subgenus Penicillium sp. This strain was deposited with the Patent Microorganism Depositary, National Institute of Technology and Evaluation, under the accession number NITE P-01785 as of December 25, 2013.

[Culture method of PF1451 substance-producing bacteria]
In the present invention, a PF1451 substance-producing bacterium, such as Penicillium sp. PF1451 strain, can be cultured 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.
As the nutrient source, known ones conventionally used for mold cultivation can be used. For example, glucose, sucrose, starch syrup, dextrin, starch, glycerol, molasses, brown rice, cereals such as rice, wheat, corn grits, animal and vegetable oils, and the like can be used as the carbon source. As the nitrogen source, soy flour, soybean meal, wheat germ, corn steep liquor, cottonseed meal, meat extract, peptone, yeast extract, 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 as necessary.
In addition, organic substances and inorganic substances that help the growth of bacteria and promote the production of the PF1451 substance can be appropriately added. Furthermore, if necessary, micronutrients such as vitamins, growth promoting substances, precursors, and the like that promote the growth of the production bacteria and the production of the PF1451 substance may be appropriately added to the medium.

  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. The production amount 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. The culture is stopped when the accumulation of PF1451 substance in the culture reaches a maximum. The culture conditions such as medium composition, medium liquidity, culture temperature, agitation speed, and aeration volume 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, an antifoaming agent such as silicone oil, vegetable oil, or 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 advantageous to purify the PF1451 substance by solvent extraction of the culture.

[PF1451 substance purification and isolation]
When purifying and isolating the PF1451 substance of the present invention from a culture of microorganisms, conventional separation means utilizing its properties, such as solvent extraction, ion exchange resin adsorption or distribution chromatography, gel filtration, dialysis, It is possible to purify and isolate by appropriately combining precipitation methods and the like.

  Specifically, after distilling off the organic solvent of the extract and concentrating, the concentrate is passed through a synthetic adsorbent (for example, Diaion HP-20, manufactured by Mitsubishi Chemical Corporation), acetone / water, methanol / The flow-through extracted with a solvent system such as water or the extract is concentrated under reduced pressure, and the resulting concentrate is added to methanol / chloroform, acetone / hexane, ethyl acetate / hexane, methanol / water, acetonitrile / water, etc. Repeated silica gel chromatography (for example, Wako Gel C300, manufactured by Wako Pure Chemical Industries) in solvent system, or ODS chromatography (for example, Cosmo Seal 75 C18-OPN, manufactured by Nacalai Tesque, TSKgel-amide-80, manufactured by Tosoh Corporation) The method of performing etc. is mentioned. If necessary, it can be purified and isolated by elution with methanol, water, etc. using gel filtration column chromatography such as Sephadex LH-20 (manufactured by Amansham Biosciences AB). .

In the present invention, an agricultural and horticultural fungicide comprising at least one PF1451A substance represented by the formula (1), PF1451B substance represented by the formula (2) or an agricultural and horticulturally acceptable salt thereof is effective. The phytopathogenic fungi to be shown are not particularly limited.
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 fungus (Mycosphaerella arachidis), black astringent fungus (Mycosphaerella berkeleyi)
Cucumber powdery mildew (Sphaerotheca fuliginea), downy mildew (Pseudoperonospora cubensis), vine blight (Mycosphaerella melonis), vine rot (Fusarium oxysporum), mycorrhizal fungus (Sclerotinia sclerotiorum), gray fungus cine ), Anthracnose fungus (Colletotrichum orbiculare), black spot fungus (Cladosporium cucumerinum), brown spot fungus (Corynespora cassicola), seedling fungus (Pythium debaryanam, Rhizoctonia solani Kuhn), spot bacterial fungus (Pseudomonas syringmans pry.
`` Tomato '' gray mold fungus (Botrytis cinerea), leaf mold fungus (Cladosporium fulvum), plague fungus (Phytophthora infestans)
Eggplant 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 leaf blight fungus (Botrytis squamosa), downy mildew (Peronospora destructor)
Cabbage root-knot fungus (Plasmodiophora brassicae), soft-rot fungus (Erwinia carotovora), downy mildew (Peronospora parasitica)
The radish (Sclerotinia sclerotiorum), white rust (Albugo macrospora), anthracnose (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)
`` Sola beans '' downy mildew (Peronospora viciae), white silkworm (Sclerotinia rolfsii)
`` Green beans '', Sclerotinia sclerotiorum, Botrytis cinerea
`` Apple '' powdery mildew (Podosphaera leucotricha), black rot (Venturia inaequalis), monilinia mali, black spot (Mycosphaerella pomi), rot (Valsa mali), spotted rot (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), homoposis spoilage fungus (Phomopsis sp.)
Mongolia fructicola
`` 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)
Of pear, Venturia nashicola, Gymnosporangium asiaticum, Black spot fungus (Alternaria kikuchiana), Ring mold fungus (Botryosphaeria berengeriana), Powdery mildew (Phyllactinia mali)
"Chesta" ring spot disease fungus (Pestalotia theae), anthrax 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. (Monographella nivalis), eye mold fungus (Pseudocercosporella herpotrichoides), leaf blight fungus (Septoria tritici), blight fungus (Leptosphaeria nodorum), snow mold fungus (Typhula incarnata), snow mold fungus (Myriosclerotinia borealis) , Gaeumanomyces graminis;
Pyrenophora graminea, cloudy fungus (Rhynchosporium secalis), naked panty fungus (Ustilago tritici, U.nuda), brown 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 niyabeanus), 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 '' sclerotia (Sclerotinia sclerotiorum), powdery mildew (Erysiphe cichoracearum), plague (Phytophthora nicotianae)
"Tulip" gray mold fungus (Botrytis cinerea)
`` Bentgrass '' Snow rot large sclerotia (Sclerotinia borealis), red rot (Pythium aphanidermatum)
Powdery mildew (Erysiphe graminis) of "Orchardgrass"
It can be used for controlling such as.

As a disease for which application of the compound of the present invention is preferable,
Aphanomyces cochlloides and sugar beet (Peronospora schachtii)
Phytophthora infestans
Cucumber downy mildew (Pseudoperonospora cubensis), seedling blight (Pythium debaryanam)
Phytophthora infestans
Eggplant brown rot fungus (Phytophthora capsici)
Strawberry plague (Phytophthora cactorum)
"Onion" downy mildew (Peronospora destructor)
"Cabbage" downy mildew (Peronospora parasitica)
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)
Brown wheat rot fungus of wheat (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
Various diseases caused by oomycetes such as And for these plant diseases, the PF1451A substance represented by the formula (1), the PF1451B substance represented by the formula (2) or their horticulture-acceptable salts, or the agricultural and horticultural use of these substances It can be controlled with an agricultural and horticultural fungicide comprising one or more of the above acceptable salts.

  Agricultural and horticultural fungicides comprising at least one PF1451A substance represented by the formula (1), PF1451B substance represented by the formula (2) or an agricultural and horticulturally acceptable salt thereof, It can also be used by mixing with insecticides, acaricides, anthelmintics, herbicides, plant growth regulators, fertilizers and the like. Drugs that can be used in combination include those listed in the Pesticide Manual (published by The British Crop Protection Council 13th edition) and Shibuya Index (published by SHIBUYA INDEX 16th edition, 2012, published by SHIBUYA INDEX RESEARCH GROUP). It is done.

More specifically, the insecticide, acaricide or nematicide is 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 (miprothrin), methfluthrin (phenothrin), praretrin (prallethrin), profluthrin (profluthrin) rethrin, pyretrin (resmethrin), tetramethrin (tetramethrin), tralomethrin, transfluthrin, permethrin, tefluthrin, cypermethrin, deltamethrin, cyhalothrin, fenvalerate (cyhalothrin) fenvalerate), Rubarineto (fluvalinate), etofenprox (ethofenprox), include silafluofen (silafluofen) 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, fenazaquin.
A-9. Examples of the mitochondrial respiratory chain complex II inhibitor 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, noiflumuron, teflubenzuron, triflumuron.
A-20. Examples of lipid biosynthesis inhibitors include spirodiclofen, spiromesifen, and spirotetramat.
A-21. Examples of octopamine-like substances include amitraz and chlordimeform.
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, 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) -methyl] -amide Or 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 WO2007006670, WO2013024008, WO2013024009, Examples include substances shown in WO2014053406 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, or pyrifluquinazon, flometoquin, afidopyropen, triflumezopyrim, triflumezopyrim Examples thereof include amidoflumet, organometallic compounds, dinitro compounds, organic sulfur compounds, urea compounds, triazine compounds, hydrazine compounds, substances represented by the following formulas, and acid addition salts thereof.

  Further, compounds represented by the following formula (A) or the following formula (B) shown in WO2012 / 029672 and WO2013 / 129692 and their agriculturally and horticulturally acceptable salts are exemplified.

式（A）

[式中、
Ａｒは、ハロゲン原子、水酸基、ハロゲン原子により置換されていてもよいＣ１〜６アルキル基、ハロゲン原子により置換されていてもよいＣ１〜６アルキルオキシ基、シアノ基、またはニトロ基のいずれかで置換されていてもよいピリジル基、あるいは、ハロゲン原子、ハロゲン原子により置換されていてもよいＣ１〜４アルキル基、ハロゲン原子により置換されていてもよいＣ１〜４アルキルオキシ基、水酸基、シアノ基、またはニトロ基のいずれかで置換されていてもよいピリミジル基を示し、
Ｙは、水素原子、ハロゲン原子、水酸基、ハロゲン原子により置換されていてもよいＣ１〜６アルキル基、ハロゲン原子により置換されていてもよいＣ１〜６アルキルオキシ基、シアノ基、またはニトロ基を示し、
Ｒ₁は、ハロゲン原子により置換されたＣ１〜６アルキル基を示す] 、
または、下記式で示されるアミン誘導体またはそれらの酸付加塩：

Formula (A)

[Where
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, or a nitro group. An optionally substituted pyridyl group, 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;
Y represents a hydrogen atom, a halogen atom, a hydroxyl group, a C1-6 alkyl group which may be substituted with a halogen atom, a C1-6 alkyloxy group which may be substituted with a halogen atom, a cyano group or a nitro group. ,
R ₁ represents a C 1-6 alkyl group substituted by a halogen atom]
Or an amine derivative represented by the following formula or an acid addition salt thereof:

式（B）

[式中、
Ａｒは、ハロゲン原子、水酸基、ハロゲン原子により置換されていてもよいＣ１〜６アルキル基、ハロゲン原子により置換されていてもよいＣ１〜６アルキルオキシ基、シアノ基、またはニトロ基のいずれかで置換されていてもよいピリジル基、あるいは、ハロゲン原子、ハロゲン原子により置換されていてもよいＣ１〜４アルキル基、ハロゲン原子により置換されていてもよいＣ１〜４アルキルオキシ基、水酸基、シアノ基、またはニトロ基のいずれかで置換されていてもよいピリミジル基を示し、
Ｒ₁は、ハロゲン原子により置換されたＣ１〜６アルキル基を示す]
が挙げられる。

Formula (B)

[Where
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, or a nitro group. An optionally substituted pyridyl group, 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]
Is mentioned.

  The pest control agent of the present invention can be used in combination or in combination with a microbial pesticide such as an entomopathogenic virus agent.

The bactericides used in combination or in combination are 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 inhibitor of 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 Examples include proline (oxathiapiprolin), NNF-0721, MIF-1002, and NF-171.
B-18. As plant disease control agents, the following JP2009-078991, JP2009-073823, WO2008 / 102678, JP2010-083763, republished WO08 / 066148, republished WO09 / 028280, WO05 / 115994, JP 2006-290883, WO07 / 072999, WO07 / 108483, WO08 / 062878, WO06 / 098128.

  An agricultural and horticultural fungicide comprising one or more PF1451 substances represented by formula (1) or formula (2) is a pharmaceutically acceptable carrier, for example, a suitable solid carrier, liquid carrier, gaseous Mixed with carriers such as carriers, surfactants, dispersants, other formulation adjuvants, emulsions, solutions, suspensions, wettable powders, flowables, powders, granules, tablets, oils, aerosols, Provided as any dosage form, such as smoke.

  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 methylnaphthalene. Aromatic hydrocarbons such as diethyl ether, dioxane, tetrahydrofuran, etc., esters such as ethyl acetate, nitriles such as acetonitrile and isobutyronitrile, acid amides such as dimethylformamide and dimethylacetamide, soybean oil , Vegetable oils such as cottonseed oil, dimethyl sulfoxide, water and the like.

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

  Surfactants and dispersants for emulsification, dispersion, spreading, etc. include, for example, alkyl sulfates, alkyl (aryl) sulfonates, polyoxyalkylene alkyl (aryl) ethers, polyhydric alcohol esters, Lignin sulfonate and the like are used.

  Moreover, as a lumber adjuvant for improving the property of a formulation, carboxymethylcellulose, gum arabic, polyethylene glycol, calcium stearate, etc. are used, for example.

  The above carrier, surfactant, dispersant, and lumber adjuvant may be used alone or in combination as required.

  The content of the active ingredient in the preparation is not particularly limited, but usually 0.5 to 75% by weight for emulsion, 0.05 to 25% by weight for powder, 0.5 to 90% by weight for wettable powder, In a granule, it is 0.05-50 weight%.

  PF1451A substance represented by formula (1), PF1451B substance represented by formula (2) or their horticulture-acceptable salt, or PF1451A substance represented by formula (1), represented by formula (2) Agricultural and horticultural fungicides comprising one or more PF1451B substances or their agricultural and horticulturally acceptable salts, or a mixture of these and other pest control agents are useful crops, specifically Sugar beet, groundnut, potato, cucumber, tomato, eggplant, strawberry, onion, cabbage, radish, lettuce, pea, broad bean, green beans, apple, oyster, peach, sweet cherry, grape, pear, tea, wheat, barley, rice, sunflower, It can also be applied to tobacco, tulips, bentgrass, orchardgrass, or genetically modified crops.

  PF1451A substance represented by formula (1), PF1451B substance represented by formula (2), PF1451A substance represented by formula (1), PF1451B substance represented by formula (2), or their agriculture Agricultural and horticultural fungicides comprising at least one acceptable salt, or a mixture of these and other pesticides as described above, is effective in plant stems and leaves, seeds, roots, tubers, bulbs, rhizomes. It can be used by applying to germinated plants, seedlings, soil, and cultivation materials.

  When the application target is plant seeds, roots, tubers, bulbs or rhizomes, suitable examples of application methods are not particularly limited as long as they do not impede osmotic transfer, but immersion methods, powder coating methods, smearing methods , Spraying method, pellet method, coating 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, tubers, bulbs, rhizomes etc. by dipping method, plant or immerse seeds, roots, tubers, bulbs, rhizomes etc. for a sufficient time for the drug to penetrate into the plant It can also be mentioned. In this case, the immersion time and temperature are appropriately determined by those skilled in the art according to the application target, the type and amount of the drug, and the like. And although it does not specifically limit as penetration transfer time, For example, it is 1 hour or more. Moreover, as temperature in osmosis | permeation transfer, it is 5-45 degreeC, for example.

  When the application object is a germinated plant and a young plant, the whole or a part thereof is treated by immersion with the agricultural and horticultural fungicide of the present invention, and applied after germination, emergence from soil, and before transplanting. It is possible to protect these plants.

  As an application method to soil, for example, a pesticide according to the present invention or a granule of a mixture with the above-mentioned other pesticides may be applied in or on soil. Preferable soil application methods include spraying, strips, grooves, and planting treatments. Here, the spraying treatment includes surface treatment over the entire area to be treated and subsequent mechanical introduction into the soil.

  Further, it is also an advantageous soil application method to be applied by irrigating the soil with a solution obtained by emulsifying or dissolving a mixture of the agricultural and horticultural fungicide according to the present invention or another pesticide described later in water. .

  Examples of the cultivation material include hydroponics water surface, sand cultivation, NFT (Nutrient Film Technique), solid medium such as rock wool cultivation, artificial soil containing vermiculite, and artificial mat for seedling, etc. An effective amount of an agro-horticultural fungicide or a mixture with other pesticides described above can be applied directly.

  The effective amount can be appropriately determined in consideration of the type and amount of the application target, temperature, etc. For example, in the case of seeds, the PF1451 substance or an agricultural and horticulturally acceptable salt thereof per 10 kg of seeds, 1g-10kg is applied.

  When processing to the foliage part of a plant, the quantity of the compound of Formula (1) or its stereoisomer is 0.1g-10kg per 10 are of arable land.

  When applied to soil, PF1451 substances or their agriculturally and horticulturally acceptable salts are 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 modifications and modification means not shown here.

(Production example)
(Production Example 1) As a culture seed medium for Penicillium sp. PF1451 strain, starch (starch) 2.0%, glucose (glucose) 1.0%, polypeptone 0.5%, wheat germ 0.6%, yeast extract 0.3%, soybean meal 0.2% and carbonic acid A medium having a composition of 0.2% calcium (pH 7.0 before sterilization) was used. The production medium used was brown rice that had sufficiently absorbed water and 0.3% soybean meal.
The 100 mL Erlenmeyer flask into which 20 mL of the seed medium was dispensed was sterilized at 121 ° C. for 20 minutes, and after inoculating one platinum loop of a slope agar culture of Penicillium sp. PF1451 strain, it was cultured with shaking at 25 ° C. for 3 days. Next, a 500 mL Erlenmeyer flask charged with 80 g of each production medium was sterilized at 121 ° C. for 20 minutes, inoculated with 3 mL of the above seed culture solution, stirred well, and then statically cultured at 25 ° C. for 14 days.

(Production Example 2) Production of PF1451 substance a) Add 32% 66% acetone water to the culture obtained in Production Example 1, and after stirring, filter, remove brown rice and bacterial cells, and wash with 50% acetone 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 1.1 L. After washing with 1.0 L of water, the mixture was developed with 2.0 L of 10% methanol water, 2.0 L of 30% methanol water, 2.0 L of 50% methanol water-1 2.0 L, 50% methanol water-2 2.0 L, and 2.0 L of methanol. Of these developing solvents, 50% aqueous methanol-1 and 2 were distilled off under reduced pressure to obtain an oily substance. This oily substance is coated with 50 g of silica gel (Wakogel C300, manufactured by Wako Pure Chemical Industries, Ltd.) and placed on top of a 150 g silica gel column (Wakogel C300, manufactured by Wako Pure Chemical Industries, Ltd.). First, 50% acetone-hexane is added. Acetone, 10% methanol-chloroform, 20% methanol-chloroform, 30% methanol-chloroform, 60% methanol-chloroform, 80% methanol-chloroform, and methanol 1.0 L each were developed as solvents. 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) Place the oily substance obtained in a) above 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% aqueous solution of 0.01% trifluoroacetic acid, 80% methanol-0.01% trifluoroacetic acid, and methanol were used as solvents. 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.
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 a flow rate of 10 ml / min from 90% acetonitrile aqueous solution to 60% acetonitrile gradient solvent, Development was performed using a PDA detector, and the active ingredient was concentrated and dried to obtain the following two fractions. (Fraction 1: 85.7 mg, Fraction 2: 30.3 mg)
Fraction 1: The obtained oily substance 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.
Fraction 2: The obtained oily substance was placed on top of a 500 g Sephadex LH-20 column (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.

(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 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 the 1% aqueous solution of xanthan gum 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 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 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 was obtained.

(Test example)
(Test Example 1) Effect on Tomato Blight
The PF1451A substance or PF1451B substance 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 give a dilution factor of 3000 times to obtain a spray solution. A sufficient amount of spray solution was sprayed on tomatoes (variety: Tiny Tim) 16 days after sowing grown in 3 cm plastic cups. On the next day of spraying, the suspension was inoculated with a zoosporangium suspension of Phytophthora infestans prepared at 10 ⁴ cells / mL, and left in a humid chamber at 21 ° C. for 24 hours. Thereafter, it was controlled in a greenhouse, and after 4 days after inoculation, the intensity of disease was visually determined according to the following criteria, and then the control value was calculated using Equation 1 and Equation 2.
[Strength of disease]
0; no disease
1; Disease area rate of true leaves is less than 20%
2; Disease area ratio of true leaves is 20% or more and less than 40%
3; Disease area ratio of true leaves is 40% or more and less than 60%
4; Disease area ratio of true leaves is 60% or more and less than 80%
5; More than 80% of disease area ratio of true leaves Formula 1 Disease severity = mean value of disease intensity / 5 X 100
Formula 2 Control value = (Severity of untreated section-Severity of treated section) / Severity of untreated section X 100
In this test, PF1451A substance and PF1451B substance showed a control value of 90 or more.

(Test Example 2) Effect on Tomato Blight
The PF1451A material 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 plastic cup were implanted, 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 static in a moist chamber of 21 ° C. I put it. Thereafter, it was controlled in a greenhouse, and after 4 days after inoculation, the intensity of disease was visually determined according to the following criteria, and then the control value was calculated using Equation 1 and Equation 2.
[Strength of disease]
0; no disease
1; Disease area rate of true leaves is less than 20%
2; Disease area ratio of true leaves is 20% or more and less than 40%
3; Disease area ratio of true leaves is 40% or more and less than 60%
4; Disease area ratio of true leaves is 60% or more and less than 80%
5; More than 80% of disease area ratio of true leaves Formula 1 Disease severity = mean value of disease intensity / 5 X 100
Formula 2 Control value = (Severity of untreated section-Severity of treated section) / Severity of untreated section X 100
In this test, the PF1451A substance showed a control value of 90 or more.

(Test Example 3) Effect on potato plague
The PF1451A material 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 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. On the next day of spraying, a zoospore suspension of Phytophthora infestans prepared to 10 ⁴ cells / mL was spray-inoculated and left in a 21 ° C. wet chamber for 24 hours. Thereafter, it was managed in a greenhouse, and after 5 days from the inoculation, the disease intensity at each leaf position was visually determined according to the following criteria, and then the control value was calculated using Equation 1 and Equation 2.
[Strength of disease]
0; no disease
1; Disease area rate of true leaves is less than 20%
2; Disease area ratio of true leaves is 20% or more and less than 40%
3; Disease area ratio of true leaves is 40% or more and less than 60%
4; Disease area ratio of true leaves is 60% or more and less than 80%
5; More than 80% of disease area ratio of true leaves Formula 1 Disease severity = mean value of disease intensity / 5 X 100
Formula 2 Control value = (Severity of untreated section-Severity of treated section) / Severity of untreated section X 100
In this test, the PF1451A substance showed a control value of 90 or more.

(Test Example 4) Effect on Japanese radish white rust
The PF1451A material was dissolved in methanol to prepare a 1 mg / mL solution. This was diluted with deionized water to 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 cultivated in a 5 cm pot. After air-drying, a spore suspension of radish white rust fungus (Albugo macrospora) prepared at 10 ⁴ cells / mL was spray-inoculated and left in a humid chamber at 21 ° C. for 24 hours. 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 Equation 3.
Formula 3 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 showed a control value of 90 or more.

(Test Example 5) Effects on cucumber downy mildew
The PF1451A material 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 obtain a dilution factor of 3000 to obtain a spray solution. A sufficient amount of spray solution was sprayed on cucumbers 14 days after sowing grown in 3 cm pots. After air drying, a zoosporangium suspension of Pseudoperonospora cubensis prepared to 10 ⁴ cells / mL was spray-inoculated and left in a humid chamber at 21 ° C. for 24 hours. Thereafter, it was managed in a greenhouse, and after 8 days after inoculation, the intensity of the first true leaf disease was visually determined according to the following criteria, and then the control value was calculated using Formula 1 and Formula 2.
[Strength of disease]
0; no disease
1; Disease area rate of true leaves is less than 5%
2; Disease area rate of true leaves is 5% or more and less than 20%
3; The incidence rate of true leaves is 20% or more and less than 40%
4; Disease area rate of true leaves is 40% or more and less than 60%
5; Disease area ratio of true leaves is 60% or more and less than 80%
6; More than 80% of true leaf disease area ratio 1 Disease severity = average value of disease intensity / 6 X 100
Formula 2 Control value = (Severity of untreated section-Severity of treated section) / Severity of untreated section 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 Bacterial Rice Seedling Blight Fungus (Pythium graminicola) was shaken and cultured 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 substance was dissolved in dimethyl sulfoxide to prepare a 12.8 mg / mL solution. A 0.8 μL solution and a 160 μL bacterial solution were mixed so that the final concentration of the PF1451A substance was 64 mg / L, and the mixture was 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.

The PF1451 substance of the present invention is useful as an active ingredient of a novel fungicide against pests.

NITE P-01785

Claims (4)

A PF1451A substance represented by the following formula (1), a PF1451B substance represented by the following formula (2), or an agricultural and horticulturally acceptable salt thereof.

Formula (1)

Formula (2)

  An agricultural and horticultural fungicide comprising at least one of the PF1451A substance, the PF1451B substance or their agriculturally and horticulturally acceptable salts according to claim 1.   A PF1451A substance or a PF1451A substance or a PF1451A substance or a PF1451A substance or a PF1451B substance according to claim 1 cultivated by culturing a microorganism having the ability to produce a PF1451A substance or a PF1451B substance belonging to the genus Penicillium PF1451B substance manufacturing method.   A farm comprising at least one of the PF1451A substance, the PF1451B substance or their horticulture-acceptable salt according to claim 1, and the PF1451A substance, PF1451B substance or their horticulture-acceptable salt according to claim 2. A method for controlling plant diseases using a horticultural fungicide.