JP2021127303A - Oxadiazoline compound or salt thereof, agricultural and horticultural antimicrobial agents containing that compound, and method of use thereof - Google Patents

Abstract

To provide an oxadiazoline compound or a salt thereof, agricultural and horticultural antimicrobial agents containing the compound, and a method of use thereof.SOLUTION: The invention provides a compound represented by the general formula (I) in the figure or a salt thereof. [In the formula (I), Q represents Q1 or Q2; and R1, R2, R3 and R4 each independently represent H, a halogen atom, an alkyl group, an alkoxy group, or the like.]SELECTED DRAWING: None

Description

The present invention relates to an agricultural and horticultural fungicide containing an oxadiazolin compound or a salt thereof as an active ingredient, and a method for using the same.

It is described that certain oxadiazole derivatives in Patent Documents 1 and 2 have bactericidal activity against the causative bacteria of plant diseases. Further, it has been shown that certain oxadiazoline derivatives in Patent Documents 3 and 4 have bactericidal activity against the causative bacteria of plant diseases, and in such documents, one methylene as a substituent of the benzene ring is used. It is not disclosed that the compound having a 5-membered or 6-membered ring imide sandwiching the compound has bactericidal activity against the causative bacteria of plant diseases.

International Publication No. 2017/055473 Pamphlet International Publication No. 2017/093348 Pamphlet International Publication No. 2019/171234 Pamphlet International Publication No. 2019/197371 Pamphlet

In crop production such as agriculture and horticulture, the damage caused by diseases is still large, and the development of new fungicides for agriculture and horticulture is desired due to factors such as the occurrence of resistant diseases to existing drugs.

As a result of diligent research to develop a novel fungicide, the present inventors have found that the compound represented by the general formula (I) of the present invention or a salt thereof is useful as a fungicide for agriculture and gardening. , The present invention has been completed.

｛式中、Ｑは、下記構造Ｑ^１又はＱ^２を示す。

Ｒ^１、Ｒ^２、Ｒ^３及びＲ^４はそれぞれ独立に、
(a1) 水素原子；
(a2) ハロゲン原子；
(a3) （Ｃ_１‐Ｃ_６）アルキル基；
(a4) （Ｃ_１‐Ｃ_６）アルコキシ基；
(a5) ハロ（Ｃ_１‐Ｃ_６）アルキル基；又は
(a6) ハロ（Ｃ_１‐Ｃ_６）アルコキシ基を示す。
Ｒ^１及びＲ^２は、それらが結合している炭素原子と共にシクロプロピル基を形成しても良い。
Ｒ^３及びＲ^４は、それらが結合している炭素原子と共にシクロプロピル基を形成しても良い。
ただし、Ｒ^１、Ｒ^２、Ｒ^３及びＲ^４の全てが同時に水素原子を示す場合を除く。｝で表される化合物又はその塩類、
［２］Ｒ^１、Ｒ^２、Ｒ^３及びＲ^４がそれぞれ独立に、
(a1) 水素原子；又は
(a3) （Ｃ_１‐Ｃ_６）アルキル基を示し、
Ｒ^１及びＲ^２は、それらが結合している炭素原子と共にシクロプロピル基を形成しても良く、Ｒ^３及びＲ^４は、それらが結合している炭素原子と共にシクロプロピル基を形成しても良い、前記の［１］に記載の化合物又はその塩類、
［３］Ｒ^１、Ｒ^２、Ｒ^３及びＲ^４がそれぞれ独立に、
(a1) 水素原子；又は
(a3) （Ｃ_１‐Ｃ_６）アルキル基を示す、前記の［１］又は［２］に記載の化合物又はその塩類、
［４］前記の［１］乃至［３］の何れかに記載の化合物又はその塩類を有効成分として含有することを特徴とする殺菌剤、
［５］前記の［４］に記載の殺菌剤の有効量を植物又は土壌に処理することを特徴とする植物病害の防除方法、
［６］前記の［１］乃至［３］の何れかに記載の化合物又はその塩類の殺菌剤としての使用、に関する。 That is, the present invention
[1] General formula (I)

{In the formula, Q represents the following structure Q ¹ or Q ² .

R ¹ , R ² , R ³ and R ⁴ are independent of each other.
(a1) Hydrogen atom;
(a2) Halogen atom;
(a3) (C _1- C ₆ ) alkyl group;
(a4) (C _1- C ₆ ) Alkoxy group;
(a5) Halo (C _1- C ₆ ) alkyl group; or
(a6) Shows a halo (C _1- C ₆ ) alkoxy group.
R ¹ and R ² may form a cyclopropyl group with the carbon atom to which they are attached.
R ³ and R ⁴ may form a cyclopropyl group with the carbon atom to which they are attached.
However, this excludes the case where all of ^{R 1} , R ² , R ³ and R ^{4 simultaneously show hydrogen atoms.} } Or a salt thereof,
[2] R ¹ , R ² , R ³ and R ⁴ are independent of each other.
(a1) Hydrogen atom; or
(a3) (C _1- C ₆ ) Shows an alkyl group and
R ¹ and R ² may form a cyclopropyl group with the carbon atom to which they are bonded, and R ³ and R ⁴ may form a cyclopropyl group with the carbon atom to which they are bonded. Good, the compound according to the above [1] or salts thereof,
[3] R ¹ , R ² , R ³ and R ⁴ are independent of each other.
(a1) Hydrogen atom; or
(a3) The compound according to the above [1] or [2] or a salt thereof, which exhibits an _{(C 1-} C _{6) alkyl group.}
[4] A bactericidal agent comprising the compound according to any one of the above [1] to [3] or a salt thereof as an active ingredient.
[5] A method for controlling plant diseases, which comprises treating a plant or soil with an effective amount of the fungicide according to the above [4].
[6] The present invention relates to the use of the compound according to any one of the above [1] to [3] or a salt thereof as a bactericidal agent.

The compound of the present invention or salts thereof has an excellent effect as a fungicide for agriculture and horticulture.

In the definition of the general formula (I) of the compound of the present invention,
"Halo" means "halogen atom" and indicates chlorine atom, bromine atom, iodine atom or fluorine atom.

The "(C _1- C ₆ ) alkyl group" means, for example, a methyl group, an ethyl group, a normal propyl group, an isopropyl group, a normal butyl group, an isobutyl group, a secondary butyl group, a tertiary butyl group, a normal pentyl group, and an isopentyl group. Group, tertiary pentyl group, neopentyl group, 2,3-dimethylpropyl group, 1-ethylpropyl group, 1-methylbutyl group, 2-methylbutyl group, normalhexyl group, isohexyl group, 2-hexyl group, 3-hexyl group , 2-Methylpentyl group, 3-Methylpentyl group, 1,1,2-trimethylpropyl group, 3,3-dimethylbutyl group, etc., linear or branched alkyl group with 1 to 6 carbon atoms Is shown.

One or two or more halogen atoms may be substituted at substitutable positions such as the above-mentioned "(C _1- C ₆ ) alkyl group" or "(C _1- C _{6) alkoxy group", and the halogen to be substituted.} When there are two or more atoms, the halogen atoms may be the same or different. These groups are referred to as "halo (C _1- C ₆ ) alkyl groups" or "halo (C _1- C ₆ ) alkoxy groups", respectively.

Examples of salts of the compound represented by the general formula (I) of the present invention include inorganic acid salts such as hydrochlorides, sulfates, nitrates and phosphates, acetates, fumarates, maleates and oxalates. Examples thereof include organic acid salts such as methane sulfonate, benzene sulfonate and paratoluene sulfonate, and salts with inorganic or organic bases such as sodium ion, potassium ion, calcium ion and trimethylammonium.

The compound represented by the general formula (I) of the present invention and salts thereof may have one or more asymmetric centers in the structural formula, and two or more kinds of optical isomers and diastereomers may be present. In some cases, the present invention also includes all optical isomers and mixtures containing them in arbitrary proportions. Further, the compound represented by the general formula (I) of the present invention and salts thereof may have two kinds of geometric isomers derived from carbon-carbon double bonds in the structural formula, but the present invention Also includes all geometric isomers and mixtures in which they are contained in arbitrary proportions.

In the compound represented by the general formula (I) of the present invention, preferred embodiments are shown below.
R ¹ , R ² , R ³ and R ⁴ are preferably independent of each other.
(a1) Hydrogen atom; or
(a3) (C _1- C ₆ ) Alkyl groups, or R ¹ and R ² form a cyclopropyl group with the carbon atom to which they are attached, or R ³ and R ⁴ are attached to them. It forms a cyclopropyl group with the carbon atom.
More preferably the R ^{1, R} 2, ^{R 3} and ^{R 4,} each independently,
(a1) Hydrogen atom; or
(a3) (C _1- C ₆ ) It is an alkyl group.
Among the compounds of the present invention or salts thereof, those having low HDAC4 inhibitory activity are preferable. Since HDAC exhibits multifaceted effects, its inhibitors are expected to be used as anticancer agents and the like. However, due to its multifaceted nature, non-selective inhibition and excessive inhibition have the potential to develop various toxicities such as teratogenicity (Herberland, M., Nat. Rev. Genet. , 2009, 10, 32-42. And Currant Pharmaceutical Design, 2014, Vol. 20, No. 00).

The various compounds of the present invention can be produced by, for example, the following production methods, but the production method of the compound of the present invention is not limited thereto.

（式中、Ｑは、前記と同じ意味を示す。） Manufacturing method 1

(In the formula, Q has the same meaning as described above.)

The compound represented by the general formula (I) of the present invention can be produced by the following step [a], but the compound of the present invention and the production method thereof are not limited thereto.
Step [a]: A step of producing a compound represented by the general formula (I) by reducing the compound represented by the general formula (II).

Production method of step [a] The compounds represented by the general formula (I) are International Publication No. 2017/093348 Pamphlet, International Publication No. 2017/213252 Pamphlet, International Publication No. 2017/055473 Pamphlet, International Publication No. 2015. / 185485 pamphlet, international publication 2017/118689 pamphlet, international publication 2017/080859 pamphlet, international publication 2013/008162 pamphlet, international publication 2017/076935 pamphlet, international publication 2015/185485 pamphlet and It can be produced by reacting a compound represented by the general formula (II), which can be produced by the method described in JP-A-63-162680, with a reducing agent in an inert solvent.

Examples of the reducing agent that can be used in this reaction include lithium aluminum hydride, sodium aluminum hydride, sodium borohydride, sodium cyanoborohydride, and the like, and the amount of the reducing agent used is a general formula ( It may be appropriately selected from the range of usually 0.25 times mol to 2 times mol with respect to the compound represented by II).

The inert solvent used in this reaction may be any solvent as long as it does not significantly inhibit the progress of this reaction. For example, aliphatic hydrocarbons such as pentane, hexane and cyclohexane; diethyl ether, methyl tertiary butyl ether and cyclopentyl methyl. Ethers such as ethers, tetrahydrofuran and dioxane; inert solvents such as alcohols such as methanol, ethanol, 1-propanol and 2-propanol can be exemplified, and these inert solvents can be used alone or in combination of two or more. Can be used. The amount to be used may be appropriately selected from the range of usually 0.1 to 100 L with respect to 1 mol of the compound represented by the general formula (II).

Since this reaction is an equimolar reaction, equimolar of each reactant may be used, but any of the reactants may be used in excess. The reaction temperature can be usually carried out in the boiling point range of the inert solvent used from room temperature, and the reaction time is not constant depending on the reaction scale and the reaction temperature, but is usually in the range of several minutes to 48 hours. After completion of the reaction, the target product may be isolated from the reaction system containing the target product by a conventional method, and the target product can be produced by purification by recrystallization, column chromatography or the like, if necessary.

Representative examples of the compound represented by the general formula (I) of the present invention are shown below in Tables 1 and 2, but the present invention is not limited thereto.
In the table, "Me" indicates a methyl group and "Et" indicates an ethyl group. Physical characteristics indicate the melting point (° C).

The agricultural and horticultural fungicides containing the compound represented by the general formula (I) of the present invention or salts thereof as an active ingredient are suitable for controlling diseases occurring in cereals, fruit trees, vegetables, other crops and flowers.

Target diseases include filamentous fungal diseases, bacterial diseases, viral diseases and the like. Filamentous fungal diseases include, for example, diseases caused by incomplete fungi (for example, Botrytis disease, Helminthosporium disease, Fusarium disease, Septoria disease, Sercospora). ) Genus disease, Pseudocercosporella genus disease, Rynchosporium genus disease, Pyricularia genus disease, Alternaria genus disease, Alternaria genus disease, etc.); Genus disease, Rhizoctonia disease, Ustylago disease, Typhula disease, Puccinia disease, etc.); Diseases caused by ascospores (eg, Venturia disease, Venturia disease) (Podosphaera) disease, Leptosphaeria disease, Blumeria disease, Elysiphe disease, Microdocium disease, Microdochium disease, Screlothinia Diseases, diseases of the genus Monilinia, diseases of the genus Unsinula, etc.); and diseases of other fungi (eg, diseases of the genus Ascochyta, diseases of the genus Phoma, diseases of the genus Phythium, cortium) (Corticium) genus disease, Pyrenophora genus disease, etc.) and the like. Bacterial diseases include, for example, Pseudomonas disease, Xanthomonas disease, Erwinia disease and the like. Examples of the virus disease include diseases caused by tobacco mosaic virus (Tabacco mosaic virus) and the like.

Specific diseases of filamentous fungal diseases include, for example, rice blast (Pyricularia oryzae), rice crest blight (Rhizoctonia solani), rice sesame leaf blight (Cochiobolus miyabeanus), rice seedling blight (Cochiobolus miyabeanus), rice seedling blight. Fusarium graminicola, Fusarium roseum, Mucor sp., Phoma sp., Tricoderma sp. ), Fusarium such as eggplant (Erysiphy cycholarum) and other host plants such as Fusarium, Omugi and wheat (Puccinia cosporella herpotorichoides), Black ear disease such as wheat (Urocystis) snow mold (Microdochium nivalis, Pythium iwayamai, Typhla ishikariensis, Typhla incarnata, Sclerotinia borealis), barley and wheat, such as Fusarium head blight (Fusarium graminearum, Fusarium avenaceum, Fusarium culmorum, Microdochium nivalis), barley and rust diseases such as wheat ( Puccinia recondita, Puccinia striformis, Puccinia graminis, Gaeumanomyces gramnis, Fusarium, Fusarium, Fusarium, Fusarium, Fusarium, Fusarium, Fusarium, Fusarium, Fusarium, Fusarium, Fusarium, Fusarium, Fusarium, Fusarium, Fusarium, Fusarium, Fusarium, Fusarium Fusarium, Fusarium, Fusarium, Fusarium, Fusarium, Fusarium, Fusarium, Fusarium, Fusarium, Fusarium, Fusarium, Fusarium, Fusarium, Fusarium, Fusarium, Fusarium, Fusarium, Fusarium, Fusarium, Fusarium, Fusarium, Fusarium, Fusarium, Fusarium, Fusarium, Fusarium, Fusarium, Fusarium, Fusarium, Fusarium Various plant vegetation diseases such as pora cubensis and Plasmopara viticola, apple scab (Venturia inaequalis), apple spot deciduous disease (Alternaria mari), pear scab (Alternaria kanchi) Disease (Diaporthe citri), citrus scab (Elsinoe fawcetti), Cercospora beticola, Cercospora arachidicola, Lakkasei black astringent disease (Cercospora) , Wheat wilt disease (Leptosphaeria nodolum), Omugi net spot disease (Pyrenophora teres), Omugi mottled leaf disease (Pyrenophora graminea), Omugi cloud-shaped disease (Rhinchosporiuma black ear) Tilletia carriers), leaf rot of wheat (Rhizoctonia solani), dollar spot disease of wheat (Cercospora homoeocarpa) and the like.

Specific diseases of bacterial diseases include diseases caused by the genus Pseudomonas, for example, Pseudomonas syringae pv. Lachrymans, Pseudomonas solara Xanthomonas, and Xanthomonas genus Xanthomonas. Diseases caused by, for example, Xanthomonas bacterium, Xanthomonas oryzae and Xanthomonas citri, diseases caused by the genus Erwinia, such as cabbage soft rot.

The useful plants to which the compound represented by the general formula (I) of the present invention or salts thereof can be used are not particularly limited, but for example, grains (for example, rice, barley, wheat, rye, oat, etc. Corn, etc.), beans (soybeans, red beans, sky beans, pea, green beans, peanuts, etc.), fruit trees / fruits (apples, citrus fruits, pears, grapes, peaches, plums, cherry blossoms, peaches, chestnuts, almonds, bananas, etc.) , Leaves and fruit vegetables (cabbage, tomato, spinach, broccoli, lettuce, onion, onion (asatsuki, split), peppers, eggplant, strawberry, pepper, okura, nira, etc.), root vegetables (carrot, horse bell, sweet potato, satoimo) , Daikon, Kabu, Renkon, Gobo, Carrot, Rakkyo, etc.), Processing crops (Cast, hemp, Beet, Hop, Sugar cane, Tensai, Olive, Rubber, Coffee, Tobacco, Tea, etc.), Cucumbers (Pumpkin, Cucumber, Tea, etc.) Squid, melon, melon, etc.), grasses (orchardgrass, sorghum, timothy, clover, alfalfa, etc.), turf (Koryo turf, bentgrass, etc.), fragrances, etc. , Pepper, ginger, etc.), flowers (kiku, roses, carnations, orchids, tulips, lilies, etc.), garden trees (chooses, cherry blossoms, aoki, etc.), forest trees (beans, beans, pine trees, hiba, cedar, etc.) Plants such as melon, melon, etc.) can be mentioned.

The above-mentioned "plants" include HPPD inhibitors such as isoxaflutol, ALS inhibitors such as imazetapill and thifensulfuronmethyl, EPSP synthase inhibitors such as glyphosate, glutamine synthase inhibitors such as gluhosinate, and setoxydim. Also included are plants that have been conferred resistance to herbicides such as acetyl CoA carboxylase inhibitors, bromoxynyl, dicamba, 2,4-D by classical breeding methods or genetic recombination techniques.

Examples of "plants" that have been endowed with resistance by classical breeding methods include rapeseed, wheat, sunflower, and rice that are resistant to imidazolinone-based ALS-inhibiting herbicides such as imazetapill, and the trade name of Clearfield (registered trademark). Already sold at. Similarly, there are soybeans resistant to sulfonylurea ALS-inhibiting herbicides such as thifensulfuronmethyl by classical breeding methods, which are already sold under the trade name of STS soybeans. Similarly, SR corn and the like are examples of plants to which resistance to acetyl-CoA carboxylase inhibitors such as trionoxime-based and aryloxyphenoxypropionic acid-based herbicides has been imparted by classical breeding methods.
Plants that have been conferred resistance to acetyl-CoA carboxylase inhibitors are the Proceedings of the National Academy of Sciences of the United States of America (Proc. Natl. Acad. Sci). USA) 87, pp. 7175-7179 (1990) and the like. In addition, mutant acetyl CoA carboxylase resistant to acetyl CoA carboxylase inhibitors has been reported in Weed Science, Vol. 53, pp. 728-746 (2005), and such mutant acetyl CoA carboxylase genes have been genetically modified. By introducing into a plant or by introducing a mutation related to resistance imparting into a plant acetyl CoA carboxylase, a plant resistant to an acetyl CoA carboxylase inhibitor can be produced. 1999. Researching the Genome's Spelling Sciences. Science 285: 316-318.) Is introduced into plant cells to introduce site-specific amino acids into plant acetyl CoA carboxylase genes, ALS genes, etc. By introducing a substitution mutation, a plant resistant to an acetyl CoA carboxylase inhibitor, an ALS inhibitor, etc. can be produced, and the compound represented by the general formula (I) of the present invention or a compound represented by the general formula (I) of the present invention can also be produced for these plants. The salts can be used.

Furthermore, as toxins expressed in recombinant plants, δ- such as bacillus cereus and bacillus popiliae-derived insecticidal proteins; Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C derived from Bacillus turingensis. Endotoxins; insecticidal proteins such as VIP1, VIP2, VIP3 or VIP3A; insecticidal proteins derived from nematodes; toxins produced by animals such as scorpion toxins, spider toxins, bee toxins or insect-specific neurotoxins; filamentous fungal toxins; plant lectin; Agglutinin; protease inhibitors such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin, papain inhibitors; ribosome inactivating proteins (RIP) such as lysine, corn-RIP, abrin, rufin, saporin, briozin; 3- Steroid metabolizing enzymes such as hydroxysteroid oxidase, exdisteroid-UDP-glucosyl transferase, cholesterol oxidase; ecdison inhibitor; HMG-CoA reductase; ion channel inhibitor such as sodium channel and calcium channel inhibitor; immature hormone esterase; diuresis Hormone receptors; stillben synthase; bibenzyl synthase; chitinase; glucanase and the like.

Further, as toxins expressed in such transgenic plants, δ-endotoxin proteins such as Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1, Cry9C, Cry34Ab or Cry35Ab; Hybrid toxins of insecticidal proteins; partially defective toxins; modified toxins are also included. Hybrid toxins are produced by new combinations of different domains of these proteins using recombinant technology. As a toxin lacking a part, Cry1Ab lacking a part of the amino acid sequence is known. As the modified toxin, one or more of the amino acids of the natural toxin have been replaced.

Examples of these toxins and recombinant plants capable of synthesizing these toxins are EP-A-0 374 753, WO 93/07278, WO 95/34656, EP-A-0 427 529, EP-A-451 878. , WO 03/052073 and the like.

The agricultural and horticultural fungicides of the present invention can be used in combination with these techniques or systematically.

The agricultural and horticultural fungicide of the present invention is used as it is for controlling various diseases, or diluted or suspended with water or the like in an amount effective for disease control for plants in which the occurrence of the disease is predicted. It may be used, for example, for diseases occurring in fruit trees, grains, vegetables, etc., in addition to spraying on the foliage, soaking seeds in chemicals, seed treatment such as seed powder coating, calper treatment, etc., mixing all layers of soil , Soil application, bed soil mixing, cell seedling treatment, planting hole treatment, plant root treatment, top dress, rice box treatment, water surface application, etc. It can also be used by treating it with soil and absorbing it from the roots. In addition, it can be applied to nutrient solution in hydroponic cultivation, and can also be used by smoke or tree trunk injection.

Further, the agricultural and horticultural fungicide of the present invention may be used as it is, or appropriately diluted with water or the like, or suspended in an amount effective for disease control in a place where the occurrence of the disease is predicted. ..

As a method of seed treatment, for example, a method of immersing seeds in a liquid state without diluting or diluting a liquid or solid preparation to allow a drug to permeate, mixing a solid preparation or a liquid preparation with seeds, and powder coating. Examples thereof include a method of treating and adhering to the surface of seeds, a method of mixing with an adhesive carrier such as a resin or a polymer and coating the seeds, and a method of spraying around the seeds at the same time as planting.
The "seed" for which the seed treatment is performed means a plant body in the early stage of cultivation used for propagation of plants, for example, for bulbs, lumps, seed potatoes, plant buds, propagules, scales, or cuttings in addition to seeds. Plants for vegetative propagation can be mentioned.

The "soil" or "cultivation carrier" of a plant when the method of use of the present invention is carried out indicates a support for cultivating a crop, particularly a support for growing roots, and the material is not particularly limited. However, any material can be used as long as it can grow plants, so-called soil, seedling mat, water, etc., and specific materials include, for example, sand, pebble, vermiculite, diatomaceous soil, agar, gel-like substance, and high. It may be a molecular substance, rock wool, glass wool, wood chips, bark or the like.

As a method of spraying on the foliage of a crop, a liquid preparation such as an emulsion or a flowable agent or a solid preparation such as a wettable powder or a granule wettable powder is appropriately diluted with water and sprayed, or a powder is sprayed. Examples include smoke.

Examples of the method of application to soil include a method of applying a liquid preparation to a plant stock or a nursery for raising seedlings without diluting or diluting it with water, and a method of applying granules to a plant stock or seedling raising. Method of spraying on nursery, etc., method of spraying powder, wettable powder, granule wettable powder, granule, etc. before sowing or transplantation and mixing with the whole soil, planting hole, cropping before sowing or before planting Examples thereof include a method of spraying a powder, a wettable powder, a granule wettable powder, a granule, etc. on the strips and the like.

As a method of applying paddy rice to a nursery box, the dosage form may differ depending on the application time such as application at the time of sowing, application during the greening period, application at the time of transplantation, etc. It can be applied with a mold. It can also be applied by mixing with hilling soil, and can be mixed with hilling soil and powder, granule wettable powder, granules, etc., for example, bed soil mixing, soil covering mixing, mixing with the entire hilling soil, and the like. Simply, the soil and various formulations may be alternately layered and applied.

As a method of application to paddy fields, solid formulations such as jumbo agents, pack agents, granules and granule wettable powders, and liquid formulations such as flowables and emulsions are usually sprayed on paddy fields in a flooded state. In addition, at the time of rice planting, an appropriate preparation can be sprayed or injected into the soil as it is or mixed with fertilizer. Further, by using a chemical solution such as an emulsion or a flowable as an inflow source of water into a paddy field such as a water outlet or an irrigation device, it can be applied labor-savingly with the supply of water.

In the field crops, from sowing to raising seedlings, the seeds or cultivation carriers close to the plants can be treated. For plants that are sown directly in the field, it is preferable to treat the seeds directly as well as the roots of the plants being cultivated. It is possible to spray treatment using granules or to irrigate a drug diluted or not diluted with water in a liquid state. It is also a preferable treatment to mix the granules with the cultivation carrier before sowing and then sow.

As the sowing of the cultivated plant to be transplanted and the treatment during the seedling raising period, in addition to the direct treatment on the seeds, the seedbed for raising seedlings is preferably irrigated with a liquid chemical or sprayed with granules. It is also preferable to treat the planting holes with granules at the time of planting or to mix them with a cultivation carrier near the transplanting site.

The compound represented by the general formula (I) of the present invention or a salt thereof is generally formulated and used in a shape convenient for use according to a conventional method for pesticide preparation.

That is, the compound represented by the general formula (I) of the present invention or a salt thereof is dissolved, separated, or suspended by blending them with an appropriate inert carrier or, if necessary, with an auxiliary agent in an appropriate ratio. Turbidity, mixing, impregnation, adsorption or adhesion, and appropriate dosage forms such as suspending agents (flowable agents), emulsions, oils, liquids, wettable powders, granule wettable powders, granules, powders, tablets, packs, It may be formulated and used as a jumbo agent, a suspension emulsion, or the like.

In addition to the active ingredient, the agricultural and horticultural fungicide of the present invention can contain, if necessary, an additive component usually used in pesticide preparations. These additive components include carriers such as solid carriers and liquid carriers, surfactants, dispersants, wetting agents, binders, tackifiers, thickeners, colorants, spreading agents, spreading agents, and antifreeze agents. , Anticaking agent, disintegrant, decomposition inhibitor and the like. In addition, if necessary, preservatives, plant pieces and the like may be used as additive components. These additive components may be used alone or in combination of two or more.

Examples of the solid carrier include natural minerals such as quartz, clay, kaolinite, pyrophyllite, sericite, talc, bentonite, acidic white clay, attapulsite, zeolite and diatomaceous earth, and inorganic salts such as calcium carbonate, ammonium sulfate, sodium sulfate and potassium chloride. , Organic solid carriers such as synthetic silicic acid, synthetic silicates, starch, cellulose, plant powders (eg, shavings, coconut husks, corn stalks, tobacco stems, etc.), plastic carriers such as polyethylene, polypropylene, polyvinylidene chloride, urea, Examples thereof include inorganic hollow bodies, plastic hollow bodies, fumed silica (white carbon) and the like. These may be used alone or in combination of two or more.

Examples of the liquid carrier include monohydric alcohols such as methanol, ethanol, propanol, isopropanol and butanol, and polyhydric alcohols such as ethylene glycol, diethylene glycol, propylene glycol, hexylene glycol, polyethylene glycol, polypropylene glycol and glycerin. Such alcohols, polyhydric alcohol compounds such as propylene glycol ether, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, cyclohexanone, ethyl ether, dioxane, ethylene glycol monoethyl ether, dipropyl ether, THF and the like. Ethers, normal paraffins, naphthenes, isoparaffins, kerosines, aliphatic hydrocarbons such as mineral oils, aromatic hydrocarbons such as benzene, toluene, xylene, solventnaphtha, alkylnaphthalene, dichloromethane, chloroform, carbon tetrachloride, etc. Halogenated hydrocarbons, ethyl acetate, diisopropylphthalate, dibutylphthalate, dioctylphthalate, esters such as dimethyl adipate, lactones such as γ-butyrolactone, dimethylformamide, diethylformamide, dimethylacetamide, amides such as N-alkylpyrrolidinone. Examples include nitriles such as acetonitrile, sulfur compounds such as dimethyl sulfoxide, vegetable oils such as soybean oil, rapeseed oil, cottonseed oil, and castor oil, and water. These may be used alone or in combination of two or more.

Examples of the surfactant used as a dispersant and a wettable powder include sorbitan fatty acid ester, polyoxyethylene sorbitan fatty acid ester, sucrose fatty acid ester, polyoxyethylene fatty acid ester, polyoxyethylene resin acid ester, and polyoxyethylene fatty acid diester. Polyoxyethylene alkyl ether, polyoxyethylene alkylaryl ether, polyoxyethylene alkyl phenyl ether, polyoxyethylene dialkyl phenyl ether, polyoxyethylene alkyl phenyl ether formalin condensate, polyoxyethylene polyoxypropylene block copolymer, polystyrene polyoxyethylene Block polymer, alkyl polyoxyethylene polypropylene block copolymer ether, polyoxyethylene alkyl amine, polyoxyethylene fatty acid amide, polyoxyethylene fatty acid bisphenyl ether, polyalkylene benzyl phenyl ether, polyoxyalkylene styryl phenyl ether, acetylene diol, polyoxy Nonionic surfactants such as alkylene-added acetylene diol, polyoxyethylene ether type silicone, ester type silicone, fluorine-based surfactant, polyoxyethylene castor oil, polyoxyethylene hydrogenated castor oil, alkyl sulfate, polyoxyethylene alkyl ether Sulfate, polyoxyethylene alkylphenyl ether sulfate, polyoxyethylene styrylphenyl ether sulfate, alkylbenzene sulfonate, alkylaryl sulfonate, lignin sulfonate, alkyl sulfosuccinate, naphthalene sulfonate, alkyl naphthalene sulfone Acidate, salt of formalin condensate of naphthalene sulfonic acid, salt of formalin condensate of alkylnaphthalene sulfonic acid, fatty acid salt, polycarboxylic acid salt, polyacrylic acid salt, N-methyl-fatty acid sarcosinate, resin acid salt, polyoxy Anionic surfactants such as ethylene alkyl ether phosphate and polyoxyethylene alkyl phenyl ether phosphate, laurylamine hydrochloride, stearylamine hydrochloride, oleylamine hydrochloride, stearylamine acetate, stearylaminopropylamine acetate, Cationic surfactants such as alkylamine salts such as alkyltrimethylammonium chloride and alkyldimethylbenzalconium chloride, amphoteric boundaries such as amino acid type or betaine type Examples include surfactants. These surfactants may be used alone or in combination of two or more.

Examples of the binder and tackifier include carboxymethyl cellulose and its salts, dextrin, water-soluble starch, xanthan gum, guar gum, sugar, polyvinylpyrrolidone, gum arabic, polyvinyl alcohol, polyvinyl acetate, sodium polyacrylate, and an average molecular weight of 6000 to 20000. Polyethylene glycol, polyethylene oxide with an average molecular weight of 100,000 to 5 million, phospholipid (eg, cephalin, lecithin, etc.) cellulose powder, dextrin, processed starch, polyaminocarboxylic acid chelate compound, crosslinked polyvinylpyrrolidone, co-weight of maleic acid and styrenes. Combined, (meth) acrylic acid-based copolymer, half-ester of polymer composed of polyhydric alcohol and dicarboxylic acid anhydride, water-soluble salt of polystyrene sulfonic acid, paraffin, terpene, polyamide resin, polyacrylic acid salt, polyoxy Examples thereof include ethylene, wax, polyvinyl alkyl ether, alkylphenol formalin condensate, synthetic resin emulsion and the like.

Thickeners include, for example, xanthan gum, guar gum, daiyutan gum, carboxymethyl cellulose, polyvinylpyrrolidone, carboxyvinyl polymers, acrylic polymers, starch compounds, water-soluble polymers such as polysaccharides, high-purity bentonite, fumed silica (fumed). Examples thereof include inorganic fine powders such as silica (white carbon).

Examples of the colorant include inorganic pigments such as iron oxide, titanium oxide and Prussian blue, alizarin dyes, azo dyes, and organic dyes such as metallic phthalocyanine dyes.

Examples of the antifreeze agent include polyhydric alcohols such as ethylene glycol, diethylene glycol, propylene glycol, and glycerin.

Auxiliary agents for preventing caking and promoting disintegration include, for example, polysaccharides such as starch, alginic acid, mannose, and galactose, polyvinylpyrrolidone, fumed silica (white carbon), ester gum, petroleum resin, sodium tripolyphosphate, and the like. Sodium hexametaphosphate, metal stearate, cellulose powder, dextrin, methacrylic acid ester copolymer, polyvinylpyrrolidone, polyaminocarboxylic acid chelate compound, sulfonated styrene / isobutylene / maleic anhydride copolymer, starch / polyacrylonitrile graft Examples include polymers.

Examples of the decomposition inhibitor include desiccants such as zeolite, raw lime and magnesium oxide, antioxidants such as phenol compounds, amine compounds, sulfur compounds and phosphoric acid compounds, and ultraviolet absorbers such as salicylic acid compounds and benzophenone compounds. Be done.

Examples of the preservative include potassium sorbate, 1,2-benzothiazolin-3-one and the like.

Furthermore, if necessary, functional spreading agents, activity enhancers such as metabolic decomposition inhibitors such as piperonyl butoxide, antifreezing agents such as propylene glycol, antioxidants such as BHT, and other supplements such as ultraviolet absorbers. Agents can also be used.

The blending ratio of the active ingredient compound can be adjusted as necessary, and may be appropriately selected from the range of 0.01 to 90 parts by weight out of 100 parts by weight of the agricultural and horticultural fungicide of the present invention. , 0.01 to 50 parts by weight (0.01 to 50% by weight based on the total weight of the agricultural and horticultural fungicide) is suitable for powders, granules, emulsions or wettable powders.

The amount of the compound represented by the general formula (I) of the present invention or a salt thereof used is various factors such as purpose, target weed, crop growth condition, weed development tendency, weather, environmental condition, dosage form, application method. Although it varies depending on the place of application, the time of application, etc., the active ingredient compound may be appropriately selected from the range of 0.001 g to 10 kg, preferably 0.01 g to 1 kg per 10 ares according to the purpose.

When using a fungicide for agriculture and horticulture containing the compound represented by the general formula (I) of the present invention or a salt thereof as an active ingredient, it is diluted to an appropriate concentration and sprayed or applied as it is.

The agricultural and horticultural fungicide of the present invention is another agricultural and horticultural insecticide, acaricide, herbicide, fungicide, for the purpose of expanding the disease to be controlled, the optimum time for control, or the purpose of reducing the amount of the drug. It can be mixed with biological pesticides and the like, and it can also be mixed with herbicides, plant growth regulators, fertilizers and the like depending on the usage situation. Representative compounds are exemplified below, but the compounds are not limited thereto.

Other agricultural and horticultural fungicides used for hanging purposes include, for example, aureofungin, azaconazole, azithiram, acypetacs, acibenzolar, acibenzolar S-methyl (acibenzolar-S-). methyl, azoxystrobin, anilazine, amisulbrom, ampropylfos, ametoctradin, allyl alcohol, aldimorph, ambam, Isotianil, isovaledione, isopyrazam, isofetamid, isoprothiolane, ipconazole, iprodione, iprovalicarb, iprovalicarb, iprovalicarb Iminoctadine, iminoctadine-albesilate, iminoctadine-triacetate, imibenconazole, uniconazole, uniconazole-P, echlomez Edifenphos, etaconazole, ethaboxam, ethirimol, etem, ethoxyquin, etridiazole, enestroburin, enoxastrobin, epoxy Conazole, oxadixyl, oxathiapiprolin, oxycarboxin, copper-8-q uinolinolate, oxytetracycline, copper-oxinate, oxpoconazole, oxpoconazole-fumarate, oxolinic acid, octhilinone, Soil fungicides such as ofurace, orysastrobin, metam-sodium, kasugamycin, carbamorph, carpropamid, carpropamid, carboxin, carboxylic (Carvone), quinazamid, quinacetol, quinoxyfen, chinomethionat, quinomethionate, captafol, captan, kiralaxyl, quinconazole. ), Quintozene, guazatine, cufraneb, cuprobam, coumoxystrobin, glyodin, griseofulvin, climbazole, cresol, cresol Kresoxim-methyl, chlozolinate, clotrimazole, chlobenthiazone, chloraniformethan, chloranil, chlorquinox, chloropicrin , Clotrimazole, chlorodinitronaphthalene, chlorothalonil, chloroneb, salicy lanilide, zarilamid, cyazofamid, diethyl pyrocarbonate, diethofencarb, cycloafuramid, cyclohexymet, dichlozoline, diclobutrazole , Dichlofluanid, cycloheximide, dichromezine, dichloran, dichlorophen, dichlone, disulfiram, ditalimfos, dithianon (Diniconazole), dinicoazole-M, zineb, dinocap, dinocton, dinosulfon, dinoterbon, dinobuton, dinopenton, dipymet ), Dipyrithione, diphenylamine, diphenoconazole, cyflufenamid, diflumetorim, cyproconazole, cyproconazole, cyprodinil, cyprodinil, cyprofuram (Simeconazole), dimethirimol, dimethomorph, cymoxanil, dimoxystrobin, ziram, silthiofam, streptomycin, streptomycin, spiroxamine ), Sedaxane, zoxamide, Dazomet ( dazomet, thiadiazin, tiadinil, thiadifluor, thiabendazole, tioxymid, thiochlorfenphim, thiophanate, thiophanate-methyl, thiophanate-methyl thifluzamide, thicyofen, thioquinox, thiram, decafentin, tecnazene, tecloftalam, tecoram, tetraconazole, debacarb , Dehydroacetic acid, tebuconazole, tebufloquin, dodicin, dodine, dodecylbenzenesulfonate bisethylenediamine copper complex salt (II) (DBEDC), dodemorph, dorazoxolone (dodemorph) drazoxolon, triadimenol, triadimefon, triazbutil, triazoxide, triamiphos, triarimol, trichlamide, triclopyricarb, tricyclazole (Tricyclazole), triticonazole, tridemorph, tributyltin oxide, triflumizole, trifloxystrobin, triforine, tolylfluanid , Tolclofos-methyl, tolprocarb, natamycin, nabam, nitrostyrene, nito Rotathal-isopropyl, nuarimol, copper nonylphenol sulfonate, halacrinate, validamycin, valifenalate, harpin protein, picarbut Razox (picarbutrazox), bixafen, picoxystrobin, picobenzamide, bithionol, bitertanol, hydroxyisoxazole, hydroxyisoxazole- potassium, binapacryl, biphenyl, piperalin, hymexazol, pyraoxystrobin, pyracarbolid, pyraclostrobin, pyraziflumid, pyrazophos pyrazophos, pyrametostrobin, pyriofenone, pyridinitril, pyridiflumetofen, pyridiflumetofen, pyrisoxazole, pyrifenox, pyrifenox pyribencarb, pyrimetanil, pyroxychlor, pyroxyfur, pyroxyfur, pyroquilon, vinclozolin, famoxadone, fenapanil, fenapanil, fenamidone, fenamidone, fenamidone Robin (fenaminstrobin), fenarimol (fenarimol), fenitropan (fenitrop) an), fenoxanil, ferimzone, ferbam, fentin, fenpiclonil, fenpyrazamine, fenbuconazole, fenfuram, fenpropidin ), Fenpropimorph, fenhexamid, phthalide, buthiobate, butylamine, bupirimate, fuberidazole, blasticidin-S , Furametpyr, furalaxyl, fluacrypyrim, fluazinam, fluoxastrobin, fluotrimazole, fluopicolide, fluopyram, fluoroimide ), Furcarbanil, fluxapyroxad, fluquinconazole, furconazole, furconazole-cis, fludioxonil, flusilazole, flusulfamide , Flutianil, flutolanil, flutriafol, furfural, furmecyclox, flumetover, flumorph, proquinazid, prochloraz , Procymidone, prothiocarb, prothioconazole, propamocarb, propico nazole, propineb, furophanate, probenazole, bromuconazole, hexachlorobutadiene, hexaconazole, hexylthiofos, bethoxazin, bethoxazin, bethoxazin benalaxyl, benalaxyl-M, benodanil, benomyl, pefurazoate, benquinox, penconazole, benzamorf, pencicuron, benzohydroxamic acid (Benzohydroxamic acid), benzovindiflupyr, bentaluron, benthiazole, benthiavalicarb-isopropyl, penthiopyrad, penflufen, boscalid , Phosdiphen, fosetyl, fosetyl-Al, polyoxins, polyoxorim, polycarbamate, folpet, formaldehyde, machine oil oil, maneb, mancozeb, mandipropamid, mandestrobin, myclozolin, myclobutanil, mildiomycin, milneb, mecarbinzid ), Metasulfocarb (methasulfocarb), metazoxolon, metam (metam), metam sodium salt (metam-sodium), metalaxy (metalaxy) l), metalaxyl-M, metiram, methyl isothiocyanate, mepthyldinocap, metconazole, metsulfovax, methfuroxam, methomi Metominostrobin, metrafenone, mepanipyrim, mefenoxam, meptyldinocap, mepronil, mebenil, methyl iodide (iodomethane), rabenzazole , Methyl bromide, benzalkonium chloride, basic copper chloride, basic copper sulfate, inorganic bactericides such as metallic silver, next Sodium hypochlorote, cupric hydroxide, wettable sulfur, calcium polysulfide, potassium hydrogen carbonate, sodium hydrogen carbonate (potassium hydrogen carbonate) Copper compounds such as sodium hydrogen carbonate, inorganic sulfur (sulfur), anhydrous copper sulfate (copper sulfate anhydride), nickel dimethyldithiocarbamate (nickel dimethyldithiocarbamate), 8-hydroxyquinolin copper (oxine copper), zinc sulfate (zinc) Sulfur), copper sulfate pentahydrate and the like can be exemplified.

Agricultural and horticultural insecticides, acaricides, and nematode insecticides used for the same purpose include, for example.
3,5-xylyl methylcarbamate (XMC), Bacillus thuringiensis aizawai, Bacillus thuringiensis israelensis, Bacillus thuringiensis japonensis, Bacillus thuringiensis kurstaki, Bacillus thuringiensis tenebrionis, Bacillus thuringiensis tenebrionis, Bacillus thuringiensis tenebrionis, Bacillus thuringiensis tenebrionis, Bacillus thuringiensis tenebrionis, Bacillus thuringiensis tenebrionis, Bacillus thuringiensis tenebrionis, Bacillus thuringiensis tenebrionis chlorfenson), DCIP (dichlorodiisopropyl ether), DD (1, 3-Dichloropropene), DDT, NAC, O-4-dimethylsulfamoylphenyl O, O-diethyl phosphorothioate (DSP), O-ethyl O-4-nitrophenyl phenylphosphonothioate (EPN), tripropylisocyanurate (TPIC), acrinathrin, azadirachtin, azinphos-methyl, acequinocyl, acetamiprid, acetoprole, acephate, abamectin ), Afidopyropen, avelmectin-B, amidoflumet, amitraz, alanycarb, aldicarb, aldoxycarb, aldrin, alpha-endosulfan ), Alpha-cypermethrin, albendazole, allethrin, isazofos, isamidofos, isoamidofos, isoxathion, isofenphos, isofenphos ocarb: MIPC), epsilon-metofluthrin, epsilon-momfluorothrin, ivermectin, imicyafos, imidac1oprid, imiprothrin, indoxacarb, esfenvalerate, esfenvalerate ), Ethion, ethiprole, etoxazole, ethofenprox, ethoprophos, etrimfos, emamectin, emamectin-benzoate, endosulfan (endosulfan) ), Empenthrin, oxamyl, oxydemeton-methyl, oxydeprofos (ESP), oxibendazole, oxfendazole, potassium oleate oleate, sodium oleate, cadusafos, kappa-bifenthrin, cartap, carbary1, carbosulfan, carbofuryl, gamma-cyhalothrin ), Xylylcarb, quinalphos, kinoprene, chinamethionat, cloethocarb, clothianidin, clofentezine, chromafenozide, chromafenozide, chlorantraniliprole), chlorethoxyfos, chlordimeform, chlordane, chlorpyriphos ( chlorpyrifos), chlorpyrifos-methyl, chlorphenapyr, chlorfenson, ch1orfenvinphos, chlorfluazuron, chlorobenzilate, chlorobenzoate (chlorobenzilate) chlorobenzoate), chloroprallethrin, kelsen (dicofol), salithion, cyhalodiamide, cyanophos (CYAP), diafenthiuron, diamidafos, cyantraniliprole, theta-cyper Permethrin (theta-cypermethrin), dienochlor, cyenopyrafen, dioxabenzofos, diofenolan, sigma-cypermethrin, cyclaniliprole, diclofenthion (dichlofenthion) Cycloprothrin, dichlorvos (DDVP), disulfoton, dinotefuryl, cyhalothrin, cyphenothrin, cyfluthrin, diflubenzuron, diflumethrin, cyflumethrin diflovidazin, cyhexatin, cypermethrin, dimethylvinphos, dimethoate, dimefluthrin, silafluofen, cyromazine, spinetram , Spirodiclofen, Spirotetramato (s) pirotetramat), spiromesifen, sulfluramid, sulprofos, sulfoxaflor, zeta-cypermethrin, diazinon, tau-fluvalinate , Dazomet, thiacloprid, thiamethoxam, tioxazafen, thiodicarb, thiocyclam, thiosultap, thiosultap-sodium, thionazin, thionazin thiometon, deet, dieldrin, tetrach1orvinphos, tetradifon, tetraniliprole, tetramethylfluthrin, tetramethrin, tebupirimfos, tebuphenozide , Tebufenpyrad, tefluthrin, teflubenzuron, demeton-S-methyl, temephos, deltamethrin, terbufos, tralopyril, tralopyril (tralomethrin), transfluthrin, triazamate, triazuron, trichlamide, trichlorphon (DEP), triflumezopyrim, triflumuron, tolfenpyrad, nared: BRP ), Nithiazine, nitenpyram, novaluron, novif lumuron, hydroprene, vaniliprole, vamidothion, parathion, parathion-methyl, halfenprox, halofenozide, bistrifluron ), Bisultap, hydramethylnon, hydroxy propyl starch, binapacryl, pyflubumide, bifenazate, bifenthrin, pymetrozine, pyracrophos pyraclorfos), pyrafluprole, pyridafenthion, pyridaben, pyridalyl, pyrifluquinazon, pyriprole, pyriproxyfen, pyrimicurb ), Pyrinostrobin, pyrimiphos-methy1, pyrethrins, fiproni1, fenazaquin, fenamiphos, bromopropylate, fenitrothion (MEP), phenoxycarb ), Fenothiocarb, phenothrin, fenobucarb, fensulfothion, fenthion (MPP), phenthoate (PAP), fenvalerate, fenpyroximate, fen Propatrin (fenpropathrin), fenbendazole (fenbendazole), pho Fosthiazate, formetanate, butathiofos, buprofezin, furathiocarb, prallethrin, fluacrypyrim, fluazaindolizine, fluazinam, fluazinam Sulfone (fluensulfone), fluxametamide, flucycloxuron, flucythrinate, fluvalinate, flufiprole, flupyradifurone, flupyrazofos, flufenerim, flufenoxystrobin, flufenoxystrobin, flufenoxystrobin , Flufenzine, flufenoprox, fluproxyfen, flubrocythrinate, fluhexafon, flubendiamide, flumethrin, flurimfen, prothiophos (flurimfen) prothiofos, protrifenbute, flonicamid, propaphos, propargite (BPPS), profenofos, profluthrin, propoxur (PHC), flometoquin, bromopropirate (bromopropylate), beta-cyfluthrin, hexaflumuron, hexythiazox, heptafluthrin, heptenophos, permethrin, benclothiaz, bendiocarb, bendiocarb ), Benximate e), benfuracarb, phoxim, phosalone, fosthiazate, fosthietan, phosphamidon, phosphocarb, phosmet (PMP), polynactins ), Formetanate, formothion, phorate, machine oil, malathion, milbemycin, milbemycin-A, milbemectin, mecarbam ), Mesulfenfos, methomyl, metaaldehyde, metaflumizone, metamidophos, metam-ammonium, metam-sodium, methiocarb , Methidathion (DMTP), methylisothiocyanate, methylneodecanamide, methylparathion, metoxadiazone, methoxychlor, methoxyphenozide, methoflutrin (methoprene), metolcarb, meperfluthrin, mevinphos, monocrotophos, monosultap, momfluorothrin, lambda-cyhalothrin, ryanodine, ryanodine , Rescalure, resmethrin, lepimectin, rotenone, hydrochloric acid Levamisol hydrochloride, fenbutatin oxide, morantel tartarate, methyl bromide, cyhexatin hydroxide, calcium cyanamide, lime sulfur Examples thereof include polysulfide, sulfur, and nicotine-sulfate.

Herbicides used for the same purpose include, for example, 1-naphthylacetamide, 2,4-PA, 2,3,6-TBA, 2,4,5-T, 2,4,5-TB, 2,4. -D, 2,4-DB, 2,4-DEB, 2,4-DEP, 3,4-DA, 3,4-DB, 3,4-DP, 4-CPA, 4-CPB, 4-CPP , MCP, MCPA, MCPA thioethyl, MCPB, ioxynil, aclonifen, azafenidin, acifluorfen, aziprotryne, azimsulfuron, ashlam, acet Crawl (acetochlor), atrazine (atrazine), atraton (atraton), anisuron (anisuron), anilophos (anilofos), abigricine (aviglycine), abscisic acid (abscisic acid), amiccarbazone (amicarbazone), amidosulfuron (amidosulfuron), amitrol (Amitrole), aminocyclopyrachlor, aminopyralid, amibuzin, amiprophos-methyl, ametridione, ametridione, ametrin, alachlor, aridochlor (amitrole), aminocyclopyrachlor, aminopyralid, amibuzin, amiprophos-methyl allidochlor, alloxydim, alorac, iofensulfuron, isouron, isocarbamid, isoxachlortole, isoxapyrifop, isoxaflu Thor (isoxaflutole), isoxaben (isoxaben), isosyl (isocil), isonoruron (isonoruron), isoproturon (isoproturon), isopropalin (isopropalin), isopolinate (isopolinate), isomethiozin (isomethiozin), inabenfide (inabenfide) , Ipf Imazamethazone, iprymidam, imazaquin, imazapic, imazapyr, imazamethapyr, imazamethabenz, imazamethabenz, imazamethabenz-methyl , Imazethapyr, imazosulfuron, indaziflam, indanofan, indolebutyric acid, uniconazole-P, eglinazine, esprocarb (Ethhametsulfuron), etamethosulfuron-methyl, ethalfluralin, ethiolate, ethychlozate ethyl, ethidimuron, etinofen, etenofen, ethephon Etholfuron, ethoxyfen, etnipromid, ethofumesate, etobenzanid, epronaz, erbon, endothal, oxadiazon, oxadiazon. Oxadiargyl, oxaziclomefone, oxasulfuron, oxapyrazon, oxyfluorfen, oryzalin, orthosulfamuron, orbencarb, cafenrole Benjichlor (cambendichlor), carbaslam (carbasulam), carfentrazone (carfentrazone), carfen Carfentrazone-ethyl, karbutilate, carbetamide, carboxazole, quizalofop, quizalofop-P, quizalofop-ethyl, xyla Clor (xylachlor), quinoclamine, quinonamid, quinclorac, quinmerac, cumyluron, cliodinate, glyphosate, glufosinate, glufosinate-P (Glufosinate-P), credazine, clethodim, cloxyfonac, clodinafop, clodinafop-propargyl, chlorotoluron, clopyralid, clopyralid (Cloproxydim), cloprop, chlorbromuron, clofop, clomazone, chlomethoxyni1, chlomethoxyfen, clomeprop, chlorazifop, chlorazine ), Cloransulam, chloranocryl, chloramben, cloransulam-methyl, chloridazon, chlorimuron, chlorimuron-ethyl, chlorsulfuron ), Chlorthal, chlorthiamid, chlortoluron, chlornitrofen, c. hlorfenac, chlorfenprop, chlorbufam, chlorflurazole, chlorflurenol, chlorprocarb, chlorpropham, chlormequat, chlormequat chloreturon, chloroxynil, chloroxuron, chloropon, saflufenacil, cyanazine, cyanatryn, di-allate, diuron, diethamquat, diethamquat Diquat, cycluron, cycloate, cycloxydim, diclosulam, cyclosulfamuron, cyclopyrimorate, dichlorprop, dicroprop- P (dichlorprop-P), dichlobenil, dichlobenil, diclohop-methyl, dichlormate, dichlormate, dichloralurea, diquat, diquat, cisanilide, disul ), Siduron, dithiopyr, dinitramine, cinidon-ethyl, dinosam, cinosulfuron, dinoceb, dinoterb, dinoterb, dinophenate (Dinoprop), cyhalofop-butyl, diphenamid, difenoxuron, difenopenten, difenzoquat, cybu tryne, cyprazine, cyprazole, diflufenican, diflufenzopyr, dipropetryn, cypromid, cyperquat, gibberellin, simazine , Dimexano, dimethachlor, dimethazon, dimethametryn, dimethenamid, simetryn, simeton, dimepiperate, dimepiperate, dimepiperate , Swep, sulglycapin, sulcotrione, sulfallate, sulfentrazone, sulfosulfuron, sulfometuron, sulfometuron-methyl ), Sekbumeton, sethoxydim, sebuthylazine, terbacil, daimuron, dazomet, dalapon, thiazafluron, thiazopyrti, thiazopyr ), Thiencarbazone, thiencarbazone-methyl, tiocarbazil, tioclorim, thiobencarb, thidiazimin, thidiazuron, thifensulfuron Fencesulfuron-methyl, desmedipham, desmetryn, tetrafl uron, thenylchlor, tebutam, tebuthiuron, terbumeton, tepraloxydim, tefuryltrione, tembotrione, delacrol, delachlor, terbacil. ), Terbucarb, terbuchlor, terbuthylazine, terbutryn, topramezone, tralkoxydim, triaziflam, triaziflam, triasulfuron, triasulfuron, triasulfuron Tri-allate, trietazine, tricamba, triclopyr, tridiphane, tritac, tritosulfuron, trifludimoxazin, trifludimoxazin (Triflusulfuron), triflusulfuron-methyl, trifluralin, trifloxysulfuron, tripropindan, tribenuron-methyl, tribenuron, Trifop, trifopsime, trimeturon, tolpyralate, naptalam, naproanilide, napropamide, nicosulfuron, nitralin, nitrofen ), Nitrofluorfen, nipyraclofen, neburon, norflurazon, noruron, barban (b) arban), paclobutrazol, paraquat, parafluron, haloxydine, halauxifen, haloxyfop, haloxyfop-P, haloxhopmethyl (haloxyfop-P) haloxyfop-methyl, halosafen, halosulfuron, halosulfuron-methyl, picloram, picolinafen, bicyclopyrone, bispyribac, sodium bispyribac (bispyribac-sodium), pydanon, pinoxaden, bifenox, piperophos, hymexazol, pyraclonil, pyrasulfotole, pyrazoxylone, pyrazosulfan pyrazosulfuron, pyrazosulfuron-ethyl, pyrazolate, bilanafos, pyraflufen-ethyl, pyriclor, pyridafol, pyrithiobac, pyrithiobac Pyrithiobac-sodium, pyridate, pyriftalid, pyribticarb, pyribenzoxim, pyrimisulfan, pyrimisulfuron, pyriminobac-methyl ), Pyroxasulfone, pyroxsulam, fenasulam, phenisopham, fenuron, fenoxasulf one), fenoxaprop, fenoxaprop-P, fenoxaprop-ethyl, phenothio1, phenoprop, phenobenzuron, Fenquinotrione, fenthiaprop, fenteracol, fentrazamide, phenmedipham, phenmedipham-ethyl, butachlor, butafenacil ), Butamifos, buthiuron, buthidazole, butylate, buturon, butenachlor, butroxydim, butralin, flazasulfuron, flazasulfuron. Prop (flamprop), furyloxyfen, prynachlor, primisulfuron-methyl, fluazifop, fluazifop-P, fluazifop-butyl ), Fluazolate, fluroxypyr, fluothiuron, fluometuron, fluoroglycofen, flurochloridone, fluorodifen, fluoronitrofen, fluoro Methyl (fluoromidine), flucarbazone (flucarbazone), flucarbazone-sodium (flucarbazone-sodium), fluchloralin (fluchloralin), flucetosulfuron (flucetosulfuron), fluthiacet, fluthiacet Fluthiacet-methyl, flupyrsulfuron, flufenacet, flufenican, flufenpyr, flupropacil, flupropanate, flupoxam, flupoxam (Fluminoxazin), flumiclorac, flumiclorac-pentyl, flumipropyn, flumezin, fluometuron, flumetsulam, fluridone, flurtamone , Fluroxypyr, pretilachlor, proxan, proglinazine, propazine, prodiamine, prosulfalin, prosulfuron, prosulfocarb ), Propaquizafop, propachlor, propazine, propanil, propyzamide, propisochlor, prohydrojasmon, propyrisulfuron , Propham, profluazol, profluuralin, prohexadione-calcium, propoxycarbazone, propoxycarbazone-sodium, profoxydim, Bromacil, brompyrazon, prometryn, prometon, bromoxynil, bromofe Noxim (bromofenoxim), bromobutide (bromobutide), bromobonil (bromobonil), floraslam (florasulam), florpyrauxifen, hexachloroacetone (hexachloroacetone), hexadinone (hexazinone), petoxamide (pethoxamid), benazolin (benazolin) (Penoxsulam), pebulate, beflubutamid, vernolate, perfluidone, bencarbazone, benzadox, benzipram, benzylaminopurine, benzthiazulone (benzylaminopurine) benzthiazuron, benzfendizone, bensulide, bensulfuron-methyl, benzoylprop, benzobicyclon, benzofenap, benzofluor ), Bentazone, pentanochlor, benthiocarb, pendimethalin, pentoxazone, benfluralin, benfuresate, hosamine, homesafen , Foramsulfuron, forchlorfenuron, maleic hydrazide, mecoprop, mecoprop-P, medinoterb, mesosurfuron, mesosulfuron Lufuron-methyl, mesotrione, mesoprazine, mesoprotryne, metazacro Le (metazachlor), metazol (methazole), metazosulfuron (metazosulfuron), metabenzthiazuron (methabenzthiazuron), metamitron (metamitron), metamihop (metamifop), metam (metam), metalpropalin (methalpropalin), methiuron (methiuron) , Methiozolin, methiobencarb, methyldymron, metoxuron, metosulon, metsulfuron, metosulfuron methyl (metsu1furon-methy1), metofuron-methy1 ), Metobenzuron, metometon, metolachlor, metribuzin, mepiquat-chloride, mefenacet, mefluidide, monalide, monalide monisouron, monuron, monochloroacetic acid, monolinuron, molinate, morfamquat, iodosulfuron, iodosulfuron-methyl-sodium ), Iodobonil, iodomethane, lactofen, linuron, rimsulfuron, lenacil, rhodethanil, calcium peroxide, methyl bromide (calcium peroxide) Methyl bromide) and the like can be exemplified.

Examples of biopesticides include nuclear polyhedrosis virus (NPV), granulosis virus (GV), cytoplasmic polyhedrosis virus (CPV), and insect poxvirus (Entomopoxi virus). Virus preparations such as EPV, Monocrossporium phymatophagum, Steinernema carpocapsae, Steinernema kushidai, Pasteuria penetrans, etc. Microbial pesticides used as insecticides, such as Trichoderma lignorum, Agrobacterium radiobactor, non-pathogenic Erwinia carotovora, Bacillus subtilis, etc. The same effect can be expected by using it in combination with a microbial pesticide used as a virus and a biopesticide used as a herbicide such as Xanthomonas campestris.

Further, as biopesticides, for example, Onshitsutsuyakobachi (Encarsia formosa), Koreman Aphidius colemani (Aphidius colemani), Shokugatama fly (Aphidoletes aphidimyza), Isaeahimekobachi (Diglyphus isaea), Hamoglyphus isaea (Dacnusa sibirica), Chili. Natural enemy organisms such as Phytoseiulus persimilis, Amblyseius cucumeris, Orius sauteri, microbial pesticides such as Beauveria brongniartii, (Z) -10-tetradecenyl-acetate, (E,) Z) -4,10-Tetradecazineiel-acetate, (Z) -8-dodecenyl-acetate, (Z) -11-tetradecenyl-acetate, (Z) -13-icosene-10-on, 14-methyl- It can also be used in combination with a pheromone agent such as 1-octadecene.

Representative examples of the present invention will be illustrated below, but the present invention is not limited thereto.

国際公開第２０１７／０９３３４８号パンフレットに記載の方法によって製造した４，４‐ジメチル‐１‐｛４‐［５‐（トリフルオロメチル）‐１，２，４‐オキサジアゾール‐３‐イル］ベンジル｝ピペリジン‐２，６‐ジオン （０．１１６ｇ，０．３１６ｍｍｏｌ）をメタノール５ｍⅬに溶かし、０℃に冷却し、水素化ホウ素ナトリウム（６．００ｍｇ，０．１５８ ｍｍｏｌ）を加え、室温で１．５時間攪拌した。その後アセトンを１ｍＬ加え、室温で１５分攪拌し、シリカゲルを加え、減圧濃縮した。残渣をシリカゲルカラムクロマトグラフィーにて精製することにより、表題の化合物（０．０２９０ｇ， ０．０７９０ｍｍｏｌ）を得た。
収率：２５％
物性値：融点２０３‐２０５℃ Example 1
4,4-Dimethyl-1- {4- [5- (trifluoromethyl) -4,5-dihydro-1,2,4-oxadiazole-3-yl] benzyl} piperidine-2,6-dione ( Production of Compound No. 1-8)

4,4-Dimethyl-1- {4- [5- (trifluoromethyl) -1,2,4-oxadiazole-3-yl] benzyl produced by the method described in WO 2017/093348. } Piperidine-2,6-dione (0.116 g, 0.316 mmol) was dissolved in methanol 5 m Ⅼ, cooled to 0 ° C., sodium boron hydride (6.00 mg, 0.158 mmol) was added, and room temperature. Was stirred for 1.5 hours. Then, 1 mL of acetone was added, the mixture was stirred at room temperature for 15 minutes, silica gel was added, and the mixture was concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give the title compound (0.0290 g, 0.0790 mmol).
Yield: 25%
Physical characteristics: Melting point 203-205 ° C

Examples of the pharmaceutical product are shown below, but the present invention is not limited thereto. In the formulation example, "part" indicates a part by weight.

Preparation example 1.
Compound represented by the general formula (I) of the present invention 10 parts Xylene 70 parts N-methylpyrrolidone 10 parts Mixture of polyoxyethylene nonylphenyl ether and calcium alkylbenzene sulfonate 10 parts or more are uniformly mixed and dissolved to form an emulsion. do.

Preparation example 2.
Compound represented by the general formula (I) of the present invention 3 parts Clay powder 82 parts Diatomaceous earth powder 15 parts or more are uniformly mixed and pulverized to obtain a powder.

Preparation example 3.
Compound represented by the general formula (I) of the present invention 5 parts Bentonite and clay mixed powder 90 parts Calcium lignin sulfonate 5 parts or more are uniformly mixed, kneaded with an appropriate amount of water, granulated and dried. Use as granules.

Formulation example 4.
Compound represented by the general formula (I) of the present invention 20 parts Mixture of kaolin and synthetic highly dispersed silicic acid 75 parts Mixture of polyoxyethylene nonylphenyl ether and calcium alkylbenzene sulfonate 5 parts or more are uniformly mixed and pulverized. Use as a wettable powder.

Test example 1. Bactericidal effect test on soybean rust disease A pot containing a compound represented by the general formula (I) of the present invention prepared according to Pharmaceutical Examples 1 to 4 as an active ingredient and diluted with water to a predetermined concentration and having a diameter of 6 cm. Soybeans (variety: Enrei, 2 leaf stage) raised in seedlings were sprayed with foliage at a ratio of 10 ml per pot. After air-drying with a chemical solution, a spore suspension prepared from spores obtained from soybean leaves infected with soybean rust fungus (Phakopsora pachyrhizi) was spray-inoculated, kept at 20 ° C. for 24 hours, and then transferred to a greenhouse for 10 hours. I left it around the day.
For the evaluation, various diseased area ratios were assessed, and the control value was calculated from the following formula 1.

(Equation 1)

判定基準
０ ： 防除価が９％以下
１ ： 防除価が１０〜１９％
２ ： 防除価が２０〜２９％
３ ： 防除価が３０〜３９％
４ ： 防除価が４０〜４９％
５ ： 防除価が５０〜５９％
６ ： 防除価が６０〜６９％
７ ： 防除価が７０〜７９％
８ ： 防除価が８０〜８９％
９ ： 防除価が９０〜９９％
１０ ： 防除価が１００％

Judgment criteria 0: Control value is 9% or less 1: Control value is 10 to 19%
2: Control price is 20-29%
3: Control value is 30-39%
4: Control value is 40-49%
5: Control price is 50-59%
6: Control value is 60-69%
7: Control value is 70-79%
8: Control price is 80-89%
9: Control price is 90-99%
10: 100% control price

As a result of the above test, among the compounds represented by the general formula (I) of the present invention, compound numbers 1-8, 1-9 and 2-4 show an effect of criteria 8 or higher at a treatment concentration of 50 ppm. rice field.

Test example 2. HDAC4 inhibitory activity measurement test <Purpose>
The HDAC inhibitory activity of the compound of the present invention is evaluated in comparison with a known compound.
<Materials and methods (test compounds and test concentrations)>
The test substance was diluted with distilled water and the concentration was set as follows. That is, each compound had a maximum concentration of 37.5 μM, and a total of 6 concentrations (0.2, 0.5, 1.4, 4.2, 12.5, 37.5 μM) were tested at a common ratio of 3 below. For the positive control agent Trichostatin A, the maximum concentration was 25 μM with reference to the package insert of the kit, and a total of 4 concentrations (0.2, 1.0, 5.0, 25 μM) were tested at a common ratio of 5 below. Distilled water was added to the solvent control instead of the test substance.

A Fluorogenic HDAC4 assay kit (BPS Bioscience, Cat No. 50064) was used to measure HDAC4 inhibitory activity. The HDAC substrate, Assay buffer, HDAC4 human recombinant enzyme and BSA (1 mg / ml) included in the kit were mixed in a predetermined amount and dispensed into a 96-well microplate. After adding the test substance solution (distilled water as a solvent control), the mixture was incubated at 37 ° C. for 30 minutes. After adding 2 × HDAC Developer and incubating at room temperature for 15 minutes, the fluorescence intensity was measured by fluorescence with a microplate reader (Em: 355, Ex: 450). The Percent of control activity was determined as the relative activity, and the 50% inhibition concentration (IC ₅₀ ) was calculated by logistic regression analysis using the relative activity at each concentration.

<Result>
_{The IC 50 of} Trichostatin A, which is an existing HDAC inhibitor that is a positive target, is 2.2 μM, whereas the compound of the present invention has an IC ₅₀ of 36.8 μM or more, and the HDAC4 inhibitory activity tends to be low. It was revealed.

The compound represented by the general formula (I) of the present invention or salts thereof has an excellent effect as a fungicide for agriculture and horticulture. Therefore, the present invention may contribute to the development of the pesticide industry, agriculture, and related fields thereof.

Claims (6)

General formula (I)

{In the formula, Q represents the following structure Q ¹ or Q ² .

R ¹ , R ² , R ³ and R ⁴ are independent of each other.
(a1) Hydrogen atom;
(a2) Halogen atom;
(a3) (C _1- C ₆ ) alkyl group;
(a4) (C _1- C ₆ ) Alkoxy group;
(a5) Halo (C _1- C ₆ ) alkyl group; or
(a6) Shows a halo (C _1- C ₆ ) alkoxy group.
R ¹ and R ² may form a cyclopropyl group with the carbon atom to which they are attached.
R ³ and R ⁴ may form a cyclopropyl group with the carbon atom to which they are attached.
However, this excludes the case where all of ^{R 1} , R ² , R ³ and R ^{4 simultaneously show hydrogen atoms.} } Or a salt thereof. R ¹ , R ² , R ³ and R ⁴ are independent of each other,
(a1) Hydrogen atom; or
(a3) (C _1- C ₆ ) Shows an alkyl group and
R ¹ and R ² may form a cyclopropyl group with the carbon atom to which they are bonded, and R ³ and R ⁴ may form a cyclopropyl group with the carbon atom to which they are bonded. A good compound according to claim 1 or a salt thereof. R ¹ , R ² , R ³ and R ⁴ are independent of each other,
(a1) Hydrogen atom; or
(a3) The compound according to claim 1 or 2, or a salt thereof, which exhibits an _{(C 1-} C _{6) alkyl group.} A bactericidal agent containing the compound according to any one of claims 1 to 3 or a salt thereof as an active ingredient. A method for controlling plant diseases, which comprises treating a plant or soil with an effective amount of the fungicide according to claim 4. Use of the compound according to any one of claims 1 to 3 or a salt thereof as a bactericidal agent.