WO2022138017A1 - Oxadiazole compound or salt thereof, and agricultural/horticultural microbicide containing said compound, and method for using same - Google Patents

Abstract

Damage caused by diseases is still significant in crop production such as in agriculture and horticulture. Thus, there has been a demand for the development of a novel agricultural/horticultural microbicide since there have been outbreaks of diseases resistant to existing chemicals.　The present invention provides: an agricultural/horticultural microbicide containing, as an active ingredient, a compound represented by general formula (I) (in the formula, R1 represents a hydrogen atom, a (C1-C6)alkyl group, or the like, R2 represents a hydrogen atom or the like, R3 represents a hydrogen atom, a (C1-C6)alkyl group, or the like, and X1 and X2 each represent a hydrogen atom, a halogen atom, or the like) or a salt thereof; and a method for using same.

Description

Oxadiazole compound or salts thereof, agricultural and horticultural disinfectants containing the compound, and methods of use thereof.

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

Patent Documents 1, 2, 3, 4, 5 and 6 describe that certain oxadiazole derivatives have bactericidal activity against the causative bacteria of plant diseases. However, the literature does not disclose or suggest a compound having a hemiaminal structure in the structure of the compound. Patent Document 7 describes that an oxazole derivative having a hemiaminal structure has a bactericidal activity against a causative bacterium of a plant disease, but discloses a compound in which an oxadiazole moiety and a hemiaminal moiety are bound to thiophene. It has not been.

Japanese Patent Application Laid-Open No. 63-162680 International Publication No. 2015/185485 Pamphlet International Publication No. 2017/055473 Pamphlet International Publication No. 2018/118781 Pamphlet International Publication No. 2018/158365 Pamphlet International Publication No. 2018/162643 Pamphlet International Publication No. 2019/13186 7 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 resistance 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 horticulture. , The present invention has been completed.

｛式中、Ｒ^１は、
(a1) 水素原子；
(a2) （Ｃ_１‐Ｃ_６）アルキル基；
(a3) （Ｃ_２‐Ｃ_６）アルケニル基；
(a4) （Ｃ_２‐Ｃ_６）アルキニル基；
(a5) （Ｃ_３‐Ｃ_６）シクロアルキル基；
(a6) ハロ（Ｃ_１‐Ｃ_６）アルキル基；
(a7) ハロ（Ｃ_２‐Ｃ_６）アルケニル基；
(a8) ハロ（Ｃ_２‐Ｃ_６）アルキニル基；又は
(a9) ハロ（Ｃ_３‐Ｃ_８）シクロアルキル基を示す。 
　Ｒ²は、
(b1) 水素原子；
(b2) （Ｃ_１‐Ｃ_６）アルキル基；
(b3) （Ｃ_２‐Ｃ_６）アルケニル基；
(b4) （Ｃ_２‐Ｃ_６）アルキニル基；
(b5) （Ｃ_３‐Ｃ_６）シクロアルキル基；
(b6) ハロ（Ｃ_１‐Ｃ_６）アルキル基；
(b7) ハロ（Ｃ_２‐Ｃ_６）アルケニル基；
(b8) ハロ（Ｃ_２‐Ｃ_６）アルキニル基；又は
(b9) ハロ（Ｃ_３‐Ｃ_８）シクロアルキル基を示す。
　Ｒ³は、
(c1) 水素原子；
(c2) （Ｃ_１‐Ｃ_６）アルキル基；
(c3) （Ｃ_２‐Ｃ_６）アルケニル基；
(c4) （Ｃ_２‐Ｃ_６）アルキニル基； 
(c5) （Ｃ_３‐Ｃ_６）シクロアルキル基；
(c6) （Ｃ_１‐Ｃ_６）アルキルカルボニル基；又は
(c7) （Ｃ_１‐Ｃ_６）アルコキシカルボニル基を示す。
　Ｘ^１及びＸ^２はそれぞれ独立に、
(e1) 水素原子；
(e2) ハロゲン原子；
(e3) シアノ基；
(e4) ニトロ基；
(e5) （Ｃ_１‐Ｃ_６）アルキル基；
(e6) （Ｃ_３‐Ｃ_６）シクロアルキル基；
(e7) （Ｃ_１‐Ｃ_６）アルコキシ基；
(e8) ハロ（Ｃ_１‐Ｃ_６）アルキル基；
(e9) ハロ（Ｃ_１‐Ｃ_６）アルコキシ基；
(e10) ハロ（Ｃ_３‐Ｃ_６）シクロアルキル基；
(e11) （Ｃ_１‐Ｃ_６）アルキルチオ基； 
(e12) （Ｃ_１‐Ｃ_６）アルキルスルフィニル基;
(e13) （Ｃ_１‐Ｃ_６）アルキルスルホニル基;
(e14) ハロ（Ｃ_１‐Ｃ_６）アルキルチオ基； 
(e15) ハロ（Ｃ_１‐Ｃ_６）アルキルスルフィニル基;又は
(e16) ハロ（Ｃ_１‐Ｃ_６）アルキルスルホニル基を示す。｝
で表される化合物又はその塩類、
［２］Ｒ^１が、
(a2) （Ｃ_１‐Ｃ_６）アルキル基；又は
(a5) （Ｃ_３‐Ｃ_６）シクロアルキル基であり、 
　Ｒ²が、
(b1) 水素原子であり、
　Ｒ³が、
(c1) 水素原子であり、
　Ｘ^１及びＸ^２が、
(e1) 水素原子である、前記［１］に記載の化合物又はその塩類、
［３］Ｒ^１が、
(a2) （Ｃ_１‐Ｃ_６）アルキル基である、前記［１］又は［２］に記載の化合物又はその塩類、
［４］前記［１］～［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農園芸用殺菌剤、
［５］前記［４］に記載の農園芸用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［１］～［３］の何れかに記載の化合物又はその塩類の農園芸用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, R ¹ is
(a1) Hydrogen atom;
(a2) (C ₁ -C ₆ ) Alkyl group;
(a3) (C ₂ -C ₆ ) alkenyl group;
(a4) (C ₂ -C ₆ ) Alkynyl group;
(a5) (C ₃ -C ₆ ) Cycloalkyl group;
(a6) Halo (C1 _{- C6} ) alkyl group;
(a7) Halo (C2 _- C- ₆ ) alkenyl group;
(a8) Halo (C2 _- C- ₆ ) alkynyl group; or
(a9) Shows a halo (C ₃ -C ₈ ) cycloalkyl group.
R ² is
(b1) Hydrogen atom;
(b2) (C ₁ -C ₆ ) Alkyl group;
(b3) (C ₂ -C ₆ ) Alkenyl group;
(b4) (C ₂ -C ₆ ) Alkynyl group;
(b5) (C ₃ -C ₆ ) Cycloalkyl group;
(b6) Halo (C- _{1 -} C6) alkyl group;
(b7) Halo (C2 _- C- ₆ ) alkenyl group;
(b8) Halo (C2 _- C- ₆ ) alkynyl group; or
(b9) Shows a halo (C ₃ -C ₈ ) cycloalkyl group.
R ³ is
(c1) Hydrogen atom;
(c2) (C ₁ -C ₆ ) Alkyl group;
(c3) (C2 _- C- ₆ ) alkenyl group;
(c4) (C2 _- C- ₆ ) alkynyl group;
(c5) (C ₃ -C ₆ ) Cycloalkyl group;
(c6) (C ₁ -C ₆ ) Alkylcarbonyl group; or
(c7) (C ₁ -C ₆ ) Shows an alkoxycarbonyl group.
X ¹ and X ² are independent of each other
(e1) Hydrogen atom;
(e2) Halogen atom;
(e3) Cyano group;
(e4) Nitro group;
(e5) (C ₁ -C ₆ ) Alkyl group;
(e6) (C ₃ -C ₆ ) Cycloalkyl group;
(e7) (C ₁ -C ₆ ) Alkoxy group;
(e8) Halo (C- ₁ -C- ₆ ) alkyl group;
(e9) Halo (C1-C _{- 6} ) alkoxy group;
(e10) Halo (C ₃ -C ₆ ) cycloalkyl group;
(e11) (C ₁ -C ₆ ) Alkylthio group;
(e12) (C ₁ -C ₆ ) Alkyl sulfinyl group;
(e13) (C ₁ -C ₆ ) Alkylsulfonyl group;
(e14) Halo (C- ₁ -C- ₆ ) alkylthio group;
(e15) Halo (C1-C _{- 6} ) alkylsulfinyl group; or
(e16) Shows a halo (C1-C _{- 6} ) alkylsulfonyl group. }
Compounds represented by or salts thereof,
[2] R ¹
(a2) (C ₁ -C ₆ ) Alkyl group; or
(a5) (C ₃ -C ₆ ) It is a cycloalkyl group and
R ² is
(b1) It is a hydrogen atom and
R ³ is
(c1) It is a hydrogen atom and
X ¹ and X ²
(e1) The compound according to the above [1] or a salt thereof, which is a hydrogen atom.
[3] R ¹
(a2) (C ₁ -C ₆ ) The compound according to the above [1] or [2] or a salt thereof, which is an alkyl group.
[4] A fungicide for agriculture and horticulture, which comprises 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 agricultural and horticultural 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 fungicide for agriculture and horticulture.

The compound of the present invention or a salt 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, tertiary pentyl group, neopentyl group, 2,3-dimethylpropyl group, 1-ethylpropyl group, 1-methylbutyl group, 2-methylbutyl group, normal hexyl 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.

The "(C2 _- C- ₆ ) alkenyl group" is, for example, a vinyl group, an allyl group, an isopropenyl group, a 1-butenyl group, a 2-butenyl group, a 2-methyl-2-propenyl group, and a 1-methyl-2. -A alkenyl group having 2 to 6 carbon atoms in a straight chain or a chain such as a propenyl group, a 2-methyl-1-propenyl group, a pentenyl group, a 1-hexenyl group, a 3,3-dimethyl-1-butenyl group, etc. The "(C2 _- C6) alkynyl group" means, for example, an ethynyl group, a ₁ -propynyl group, a 2-propynyl group, a 1-butynyl group, a 2-butynyl group, a 3-butynyl group, and a 3-methyl-. Linear or split chain such as 1-propynyl group, 2-methyl-3-propynyl group, pentynyl group, 1-hexynyl group, 3-methyl-1-butynyl group, 3,3-dimethyl-1-butynyl group, etc. Shows an alkynyl group having 2 to 6 carbon atoms.

The "(C ₃ -C ₆ ) cycloalkyl group" indicates, for example, a cyclic alkyl group having 3 to 6 carbon atoms such as a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group, and "(C ₁ ). -C ₆ ) alkoxy group, for example, methoxy group, ethoxy group, normalpropoxy group, isopropoxy group, normalbutoxy group, secondary butoxy group, tertiary butoxy group, normalpentyloxy group, isopentyloxy group, Tasha. Leepentyloxy group, neopentyloxy group, 2,3-dimethylpropyloxy group, 1-ethylpropyloxy group, 1-methylbutyloxy group, normalhexyloxy group, isohexyloxy group, 1,1,2-trimethyl A linear or branched alkoxy group having 1 to 6 carbon atoms such as a propyloxy group is shown.

The "(C ₁ -C ₆ ) alkyl thio group" means, for example, a methyl thio group, an ethyl thio group, a normal propyl thio group, an isopropyl thio group, a normal butyl thio group, a secondary butyl thio group, a tertiary butyl thio group, a normal pen tyl thio. Group, isopentylthio group, tertiary pentylthio group, neopentylthio group, 2,3-dimethylpropylthio group, 1-ethylpropylthio group, 1-methylbutylthio group, normalhexylthio group, isohexylthio group , 1,1,2-trimethylpropylthio group, etc., indicates a linear or branched alkylthio group having 1 to 6 carbon atoms.

The “(C ₁ -C ₆ ) alkyl sulfinyl group” means, for example, a methyl sulfinyl group, an ethyl sulfinyl group, a normal propyl sulfinyl group, an isopropyl sulfinyl group, a normal butyl sulfinyl group, a secondary butyl sulfinyl group, a tertiary butyl sulfinyl group, and the like. Normal Pentyl Sulfinyl Group, Isopentyl Sulfinyl Group, Terriary Pentyl Sulfinyl Group, Neopentyl Sulfinyl Group, 2,3-Dimethylpropyl Sulfinyl Group, 1-Ethylpropyl Sulfinyl Group, 1-Methylbutyl Sulfinyl Group, Normalhexyl Sulfinyl Group, Iso A linear or branched alkylsulfinyl group having 1 to 6 carbon atoms, such as a hexylsulfinyl group and a 1,1,2-trimethylpropylsulfinyl group, is shown.

The "(C ₁ -C ₆ ) alkyl sulfonyl group" means, for example, a methyl sulfonyl group, an ethyl sulfonyl group, a normal propyl sulfonyl group, an isopropyl sulfonyl group, a normal butyl sulfonyl group, a secondary butyl sulfonyl group, a tertiary butyl sulfonyl group, and the like. Normal pentylsulfonyl group, isopentylsulfonyl group, tertiary pentylsulfonyl group, neopentylsulfonyl group, 2,3-dimethylpropylsulfonyl group, 1-ethylpropylsulfonyl group, 1-methylbutylsulfonyl group, normalhexylsulfonyl group, iso A linear or branched alkylsulfonyl group having 1 to 6 carbon atoms such as a hexylsulfonyl group and a 1,1,2-trimethylpropylsulfonyl group is shown.

The "(C ₁ -C ₆ ) alkylcarbonyl group" means, for example, an acetyl group, a propanoyl group, a butanoyl group, a 2-methylpropanol group, a pentanoyl group, a 2-methylbutanoyl group, a 3-methylbutanoyl group, and the like. An alkylcarbonyl group having 2 to 7 carbon atoms, such as an alkylcarbonyl group having the above (C- ₁ -C- ₆ ) alkyl group such as a pivaloyl group, a hexanoyl group and a cyclopropylcarbonyl group, is shown.

The "(C ₁ -C ₆ ) alkoxycarbonyl group" means, for example, a methoxycarbonyl group, an ethoxycarbonyl group, a normal propoxycarbonyl group, an isopropoxycarbonyl group, a normal butoxycarbonyl group, an isobutoxycarbonyl group, a secondary butoxycarbonyl group, and the like. Indicates an alkoxycarbonyl group having 2 to 7 carbon atoms, such as an alkoxycarbonyl group having the above-mentioned (C1 _- C ₆ ) alkoxy group such as a tertiary butoxycarbonyl group or a pentyloxycarbonyl group.

The above-mentioned "(C ₁ -C ₆ ) alkyl group", "(C ₂ -C ₆ ) alkenyl group", "(C ₂ -C ₆ ) alkynyl group", "(C ₃ -C ₆ ) cycloalkyl group", "(C ₁ -C ₆ ) alkoxy group", "(C ₁ -C ₆ ) alkylthio group", "(C ₁ -C ₆ ) alkyl sulfinyl group" or "(C ₁ -C ₆ ) alkyl sulfonyl group" etc. One or two or more halogen atoms may be substituted at the substitutable positions of the above, and when the number of substituted halogen atoms is two or more, the halogen atoms may be the same or different. "Halo (C ₁ -C ₆ ) alkyl group", "halo (C ₂ -C ₆ ) alkenyl group", "halo (C ₂ -C ₆ ) alkynyl group", "halo (C ₃ -C ₆ )", respectively. Cycloalkyl group, halo (C ₁ -C ₆ ) alkoxy group, halo (C ₁ -C ₆ ) alkyl thio group, halo (C ₁ -C ₆ ) alkyl sulfinyl group or halo (C ₁ ) -C ₆ ) Alkylsulfonyl group ".

Expressions such as "(C ₁ -C ₆ )", "(C ₂ -C ₆ )", and "(C ₃ -C ₆ )" indicate the range of carbon atoms of various substituents. Further, the above definition can be shown for a group to which the above substituents are linked. For example, in the case of "(C1 _- C _{- 6} ) alkoxy (C1 _- C6) alkyl group", it is linear or branched. It is shown that the alkoxy group having 1 to 6 carbon atoms is bonded to the linear or branched alkyl group having 1 to 6 carbon atoms.

The "aryl group" and "aryl" refer to an aromatic hydrocarbon group having 6 to 10 carbon atoms, such as a phenyl group and a naphthyl group.

The "heteroaryl group" and "heteroaryl" are, for example, a frill group, a thienyl group, a pyridyl group, a pyrimidinyl group, a pyridazinyl group, a pyrazinyl group, a pyrrolyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group and an oxazolyl group. , Isooxazolyl group, oxadiazolyl group, thiadiazolyl group, triazolyl group, tetrazolyl group, triazinyl group and the like, monocyclic aromatic heterocyclic group and the like.

Examples of the 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 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 a carbon-carbon double bond in the structural formula thereof, but the present invention Also includes all geometric isomers and mixtures containing them in arbitrary proportions.

The following is a preferred embodiment of the compound represented by the general formula (I) of the present invention.
Preferably as ^R1
(a2) (C ₁ -C ₆ ) Alkyl group; or
(a5) (C ₃ -C ₆ ) It is a cycloalkyl group and
Especially preferably
(a2) (C ₁ -C ₆ ) Alkyl group.
Preferably as R ²
(b1) It is a hydrogen atom.
Preferably as R ³
(c1) It is a hydrogen atom.
Preferably as X ¹ and X ² .
(e1) It is a hydrogen atom.

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、Ｒ^１、Ｘ^１及びＸ^２は前記と同じ意味を示す。） Manufacturing method 1

(In the formula, R ¹ , X ¹ and X ² have the same meanings as described above.)

The compound represented by the general formula (Ia) of the present invention can be produced by the following steps [a] to [f].
Step [a] A step of producing a compound represented by the general formula (8) by reacting the compound represented by the general formula (10) with ethylene glycol represented by the formula (9).
Step [b] A step of producing a compound represented by the general formula (7) by cyanating the compound represented by the general formula (8).
Step [c] A step of producing a compound represented by the general formula (5) by reacting the compound represented by the general formula (7) with the hydroxylamine hydrochloride represented by the formula (6).
Step [d] A step of producing a compound represented by the general formula (3) by reacting the compound represented by the general formula (5) with the trifluoroacetic anhydride represented by the formula (4). ..
Step [e] A step of producing a compound represented by the general formula (2) by deprotecting the compound represented by the general formula (3).
Step [f] A step of producing a compound represented by the general formula (Ia) of the present invention by reacting the compound represented by the general formula (2) with the compound represented by the general formula (1). ..

Method for Producing Step [a] The compound represented by the general formula (8) is a compound represented by the general formula (10) and ethylene glycol represented by the formula (9) in the presence of an acid catalyst and an inert solvent. It can be produced by reacting with.

Examples of the acid catalyst that can be used in this reaction include methyl sulfonic acid, p-toluene sulfonic acid, trifluoromethane sulfonic acid, and the like, and the amount used thereof is relative to the compound represented by the general formula (10). Usually, it may be appropriately selected from the range of 0.01 times to 5 times mol.

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; aromatic hydrocarbons such as benzene, toluene and xylene Hydrogens; halogenated hydrocarbons such as methylene chloride, chloroform and carbon tetrachloride; inert solvents such as halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene can be exemplified, and these inert solvents can be exemplified. It can be used alone or in combination of two or more. 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 (10).

Since this reaction is an equimolar reaction, it is sufficient to use equimolar of each reactant, but any of the reactants can be excessively used. The reaction temperature can be usually carried out from room temperature in the boiling point range of the used inert solvent, and the reaction time is not constant depending on the reaction scale and the reaction temperature, but may be usually carried out in the range of several minutes to 48 hours. After completion of the reaction, the desired 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.

Production Method of Step [b] The compound represented by the general formula (7) is produced by reacting the compound represented by the general formula (8) with copper (I) cyanide in the presence of an inert solvent. be able to.

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; aromatic hydrocarbons such as benzene, toluene and xylene. Hydrogens; Halogenized hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride; Halogenized aromatic hydrocarbons such as chlorobenzene and dichlorobenzene; Esters such as ethyl acetate and propyl acetate; acetonitrile, propionitrile and the like Examples of inert solvents such as nitriles; amides such as dimethylformamide and dimethylacetamide; ketones such as acetone and methylethylketone; and aprotonic polar solvents such as dimethylsulfoxide and 1,3-dimethyl-2-imidazolidinone. These inert solvents can be used alone or in admixture of two or more. 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 (8).

Since this reaction is an equimolar reaction, equimolar of each reactant may be used, but any of the reactants may be excessively used. The reaction temperature can be usually carried out from room temperature in the boiling point range of the used inert solvent, and the reaction time is not constant depending on the reaction scale and the reaction temperature, but may be usually carried out in the range of several minutes to 48 hours. After completion of the reaction, the desired 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.

Method for Producing Step [c] The compound represented by the general formula (5) is a compound represented by the general formula (7), and the hydroxylamine hydrochloride represented by the formula (6) in the presence of a base and an inert solvent. It can be produced by reacting with a salt.

Examples of the bases that can be used in this reaction include hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide, and calcium hydroxide; sodium methoxide, sodium ethoxide, sodium tertiary butoxide, and potassium tertiary butoki. Alcoxide such as side; carbonates such as lithium carbonate, lithium hydrogencarbonate, sodium carbonate, sodium hydrogencarbonate, potassium carbonate, potassium hydrogencarbonate, calcium carbonate, magnesium carbonate; acetates such as lithium acetate, sodium acetate, potassium acetate; pyridine , Picolin, lutidine, triethylamine, tributylamine, diisopropylethylamine and other organic bases, and the amount used is usually in the range of 1 to 10 times mol with respect to the compound represented by the general formula (7). Will be done.

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, amides such as dimethylformamide and dimethylacetamide; dimethyl sulfoxide, 1,3-dimethyl-2-imidazolidi Non-protonic polar solvents such as non-protonic polar solvents; inert solvents such as alcohols such as methanol, ethanol and 2-propanol can be exemplified, and these inert solvents can be used alone or in admixture of two or more. can. 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 (7).

Since this reaction is an equimolar reaction, it is sufficient to use equimolar of each reactant, but any of the reactants can be excessively used. The reaction temperature can be usually carried out from room temperature in the boiling point range of the used inert solvent, and the reaction time is not constant depending on the reaction scale and the reaction temperature, but may be usually carried out in the range of several minutes to 48 hours. After completion of the reaction, the desired 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.

Method for Producing Step [d] The compound represented by the general formula (3) is a compound represented by the general formula (5) and trifluoroacetic acid represented by the formula (4) in the presence of a base and an inert solvent. It can be produced by reacting with an anhydride.

Examples of the bases that can be used in this reaction include hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide, and calcium hydroxide; sodium methoxide, sodium ethoxide, sodium tertiary butoxide, and potassium tertiary butoki. Alcoxide such as side; carbonates such as lithium carbonate, lithium hydrogencarbonate, sodium carbonate, sodium hydrogencarbonate, potassium carbonate, potassium hydrogencarbonate, calcium carbonate, magnesium carbonate; acetates such as lithium acetate, sodium acetate, potassium acetate; pyridine , Picolin, lutidine, triethylamine, tributylamine, diisopropylethylamine and other organic bases, and the amount used is usually in the range of 1 to 10 times mol with respect to the compound represented by the general formula (5). Will be done.

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; aromatic hydrocarbons such as benzene, toluene and xylene. Hydrogens; Halogenized hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride; Halogenized aromatic hydrocarbons such as chlorobenzene and dichlorobenzene; Esters such as ethyl acetate and propyl acetate; acetonitrile, propionitrile and the like Examples of inert solvents such as nitriles; amides such as dimethylformamide and dimethylacetamide; ketones such as acetone and methylethylketone; and aprotonic polar solvents such as dimethylsulfoxide and 1,3-dimethyl-2-imidazolidinone. These inert solvents can be used alone or in admixture of two or more. 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 (5).

Since this reaction is an equimolar reaction, it is sufficient to use equimolar of each reactant, but any of the reactants can be excessively used. The reaction temperature can be usually carried out from room temperature in the boiling point range of the used inert solvent, and the reaction time is not constant depending on the reaction scale and the reaction temperature, but may be usually carried out in the range of several minutes to 48 hours. After completion of the reaction, the desired 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.

Method for Producing Step [e] The compound represented by the general formula (2) is obtained by removing the acetal-protected aldehyde group of the compound represented by the general formula (3) by a deprotection reaction generally used in organic chemistry. It can be manufactured by protecting it.
Method for Producing Step [f] The compound represented by the general formula (Ia) of the present invention includes the compound represented by the general formula (2), the formamide represented by the formula (1) and the compound represented by the formula (1) in the presence of an inert solvent. It can be produced by reacting with a titanium compound.

Examples of the titanium compound that can be used in this reaction include titanium (IV) methoxydo, titanium (IV) ethoxydo, titanium (IV) n-propoxide, titanium (IV) i-propoxide, and titanium (IV) n. -Butoxide, titanium (IV) t-butoxide, etc. can be mentioned, and the amount to be used can be appropriately selected from the range of usually 1 to 5 times mol with respect to the compound represented by the general formula (2). good.

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; aromatic hydrocarbons such as benzene, toluene and xylene. Hydrogens; Halogenized hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride; Halogenized aromatic hydrocarbons such as chlorobenzene and dichlorobenzene; Esters such as ethyl acetate and propyl acetate; acetonitrile, propionitrile and the like Examples of inert solvents such as nitriles; amides such as dimethylformamide and dimethylacetamide; ketones such as acetone and methylethylketone; and aprotonic polar solvents such as dimethylsulfoxide and 1,3-dimethyl-2-imidazolidinone. These inert solvents can be used alone or in admixture of two or more. 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 (2).

Since this reaction is an equimolar reaction, equimolar of each reactant may be used, but any of the reactants may be excessively used. The reaction temperature can be usually carried out from room temperature in the boiling point range of the used inert solvent, and the reaction time is not constant depending on the reaction scale and the reaction temperature, but may be usually carried out in the range of several minutes to 48 hours. After completion of the reaction, the desired 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.

The following is an example of typical examples of the compound represented by the general formula (I) of the present invention in Table 1, but the present invention is not limited thereto.
In the table, "Me" is a methyl group, "Et" is an ethyl group, "n-Pr" is a normal propyl group, "i-Pr" is an isopropyl group, and "c-Pr" is a cyclopropyl group. , "N-Bu" indicates a normal butyl group, "i-Bu" indicates an isobutyl group, and "s-Bu" indicates a secondary butyl group. Physical characteristics indicate melting point (° C.) or refractive index n _D (measured temperature).

The agricultural and horticultural fungicide containing the compound represented by the general formula (I) of the present invention or a salt thereof as an active ingredient is 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, Helmintspirium disease, Fusarium disease, Septria disease, Sercospora). ) Genus disease, Pseudocercosporella genus disease, Rynchosporium genus disease, Pyricularia 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 (Leptosphaeria) disease, Blumeria (Blumeria) disease, Elysipe (Erysipe) disease, Microdocium (Microdochium) disease, Sclerothinia (Sclerotini) 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, cortisium). (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, powdery mildew (Pyricularia oryzae), powdery mildew (Rhizoctonia solani), powdery mildew (Cochiobolus myyabeanus), and rice seedling powdery mildew (Pyricularia oryzae). Fusarium glinicola, Fusarium roseum, Mucor sp., Phoma sp., Trichoderma sp.), Rice idiot seedling disease (Gibberella fujikuroi), powdery mildew such as omegi and wheat, powdery mildew (Blumeri) ), Powdery mildew such as eggplant (Eryshipe cichoracoarum) and powdery mildew of other host plants, eye print disease such as wheat and wheat (Pseudocercosporella herpotorichoides), kurocho disease such as wheat (Urocystis)雪腐病（Ｍｉｃｒｏｄｏｃｈｉｕｍ　ｎｉｖａｌｉｓ，Ｐｙｔｈｉｕｍ　ｉｗａｙａｍａｉ，Ｔｙｐｈｌａ　ｉｓｈｉｋａｒｉｅｎｓｉｓ，Ｔｙｐｈｌａ　ｉｎｃａｒｎａｔａ，Ｓｃｌｅｒｏｔｉｎｉａ　ｂｏｒｅａｌｉｓ）、オオムギ及びコムギ等の赤かび病（Ｆｕｓａｒｉｕｍ　ｇｒａｍｉｎｅａｒｕｍ，Ｆｕｓａｒｉｕｍ　ａｖｅｎａｃｅｕｍ，Ｆｕｓａｒｉｕｍ　ｃｕｌｍｏｒｕｍ，Ｍｉｃｒｏｄｏｃｈｉｕｍ　ｎｉｖａｌｉｓ）、オオムギ及びコムギ等のさび病（ Puccinia recondita, Puccinia striformis, Puccinia graminis), Gaeumannomyces graminis such as corn and wheat, powdery mildew of Enbaku, powdery mildew (Puccinia), powdery mildew, etc. Powdery mildew, powdery mildew, powdery mildew, powdery mildew, powdery mildew, powdery mildew, powdery mildew, powdery mildew, powdery mildew, powdery mildew, powdery mildew, powdery mildew, powdery mildew, powdery mildew, powdery mildew, powdery mildew, powdery mildew, powdery mildew, powdery mildew, powdery mildew, powdery mildew, powdery mildew, powdery mildew, and powdery mildew. Various plant vegetation diseases such as viticola), apple scab (Venturia inaequalis), apple spot deciduous disease (Alternaria mari), pear black spot disease (Alternaria kikuchiana), citrus black spot disease (Diaporthe citrus) (Elsinoe fawcetti), Cercospora beticola, Cercospora arachidicola, Cercospora persona, wheat leaf blight (Septori), wheat leaf blight (Septori) Cercospora beetle (Pyrenophora teres), Cercospora beetle (Pyrenophora graminea), Cercospora beetle (Rhynchosporium secalis), Cercospora beetle (Ustilago nuda), Wheat scab (Cercospora beetle) Rhizoctonia solani), Cercospora spot disease (Cercospora homoeocarpa) and the like.

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

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, potato, etc. Potatoes, etc.), beans (soybeans, red beans, sky beans, green onions, green onions, peanuts, etc.), fruit trees / fruits (apples, citrus fruits, pears, grapes, peaches, plums, cherry blossoms, melons, chestnuts, almonds, bananas, etc.) , Leaves and fruit vegetables (cabbet, tomato, spinach, broccoli, lettuce, onion, green onion (asatsuki, scallions), peppers, eggplant, strawberry, pepper, okura, nira, etc.), root vegetables (carrot, potato, sweet potato, satoimo) , Daikon, Kabu, Renkon, Gobo, Garlic, Rakkyo, etc.), Processing crops (Potato, Hemp, Beet, Hop, Satoukibi, Tensai, Olive, Rubber, Coffee, Tobacco, Tea, etc.), Uri (Potato, 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, rose, carnation, orchid, tulip, lily, etc.), garden trees (chocolate, cherry, aoki, etc.), forest trees (beans, pine, pine, hiba, cedar, etc.) Plants such as leeks, melons, 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 glufosinate, and setoxydim. Also included are plants that have been imparted to resistance to herbicides such as acetyl CoA carboxylase inhibitors, bromoxinyl, 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 soybean. 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 a classical breeding method.
In addition, plants 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), etc. Mutant acetyl CoA carboxylase resistant to acetyl CoA carboxylase inhibitors has been reported in Weed Science, Vol. 53, pp. 728-746 (2005), etc., and such a mutant acetyl CoA carboxylase gene is used as a gene recombination technique. By introducing into plants or by introducing mutations related to resistance imparting into plant acetyl CoA carboxylase, plants resistant to acetyl CoA carboxylase inhibitors can be produced, and further, chimera plasti technology (Gura T. et al. 1999. Site-specific amino acids such as plant acetyl CoA carboxylase gene and ALS gene by introducing a base substitution mutation-introducing nucleic acid represented by (Repairing the Genome's Spelling Sciences. Science 285: 316-318.) Into plant cells. By introducing a substitution mutation, plants resistant to acetyl CoA carboxylase inhibitors, ALS inhibitors, etc. can be produced, and the compounds represented by the general formula (1) of the present invention can also be produced for these plants. The salts can be used.

Further, as toxins expressed in recombinant plants, insecticidal proteins derived from Bacillus cereus and Bacillus popilia; δ- such as 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 lectins; Aglutinin; 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, briodin; 3- Steroid-metabolizing enzymes such as hydroxysteroid oxidase, ecdisteroid-UDP-glucosyltransferase, cholesterol oxidase; ecdison inhibitor; HMG-CoA reductase; ion channel inhibitor such as sodium channel and calcium channel inhibitor; immature hormone esterase; diuresis Toxin receptors; stillben synthase; bibenzyl synthase; chitinase; glucanase and the like can be mentioned.

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 created using recombinant techniques with new combinations of different domains of these proteins. 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 disinfectant of the present invention can be used in combination with these techniques or systematically.

The agricultural and horticultural bactericidal agent of the present invention is used as it is for controlling various diseases, or appropriately diluted or suspended with water or the like, and an effective amount for controlling the diseases is applied to plants in which the occurrence of the diseases 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 It can also be used by treating it with soil, etc. and absorbing it from the roots, such as cropping, soil mixing, cell seedling treatment, planting hole treatment, stock root treatment, top dress, rice box treatment, water surface application, etc. In addition, it can also be applied to nutrient solution in hydroponic cultivation, 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 the 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, tubers, 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 may 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 crops, 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. A method of spraying on a nursery, a method of spraying powder, wettable powder, granule wettable powder, granules, etc. before sowing or transplanting and mixing with the whole soil, planting holes before sowing or before planting plants, cropping Examples thereof include a method of spraying a powder, a wettable powder, a granule wettable powder, a granule, etc. on a strip or the like.

As a method of applying the paddy rice to the 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. You may simply apply the soil and various formulations in layers alternately.

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 flooded paddy fields. In addition, when planting rice, the appropriate formulation 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 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.

For field crops, it is possible to treat seeds or cultivation carriers close to plants from sowing to seedling raising. In the case of plants sown directly in the field, it is preferable to treat the seeds directly or to the root of the plant being cultivated. It is possible to spray treatment using granules or to irrigate a drug diluted or not diluted with water in liquid form. It is also a preferable treatment to mix the granules with the cultivation carrier before sowing and then sow.

As the sowing and seedling raising stage treatment of the cultivated plant to be transplanted, in addition to the direct treatment to the seeds, the irrigation treatment of the liquid chemical or the spraying treatment of the granules is preferable to the nursery for raising seedlings. 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 suspensions (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.

The agricultural and horticultural fungicide of the present invention can contain, if necessary, an additive component usually used in an agrochemical preparation in addition to the active ingredient. 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. , Anti-caking agent, disintegrating agent, anti-decomposition agent 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, pyrofylite, sericite, talc, bentonite, acidic clay, attapargite, 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 silicate, starch, cellulose, plant powder (eg, shavings, coconut husks, corn stalks, tobacco stalks, etc.), plastic carriers such as polyethylene, polypropylene, polyvinylidene chloride, urea, Examples thereof include an inorganic hollow body, a plastic hollow body, and fumed silica (white carbon). 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. Alcohols such as, 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 paraffin, naphthene, isoparaffin, kerosine, aliphatic hydrocarbons such as mineral oil, 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 alkylphenyl ether, polyoxyethylene dialkylphenyl ether, polyoxyethylene alkylphenyl ether formalin condensate, polyoxyethylene polyoxypropylene block copolymer, polystyrene polyoxyethylene Block polymer, alkyl polyoxyethylene polypropylene block copolymer ether, polyoxyethylene alkylamine, 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 cured 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 Acids, salts of formalin condensates of naphthalene sulfonic acid, salts of formalin condensates of alkylnaphthalene sulfonic acid, fatty acid salts, polycarboxylates, polyacrylic acid salts, N-methyl-fatty acid sarcosinates, resin acid salts, polyoxy Anionic surfactants such as ethylene alkyl ether phosphates and polyoxyethylene alkyl phenyl ether phosphates, laurylamine hydrochlorides, stearylamine hydrochlorides, oleylamine hydrochlorides, stearylamine acetates, stearylaminopropylamine acetates, Cationic surfactants such as alkylamine salts such as alkyltrimethylammonium chloride, alkyldimethylbenzalconium chloride, amino acid type or betaine type and the like. 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, citrus sugar, polyvinylpyrrolidone, arabic rubber, polyvinyl alcohol, polyvinylacetate, 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.

Examples of the thickener include xanthan gum, guar gum, daiyutan gum, carboxymethyl cellulose, polyvinylpyrrolidone, carboxyvinyl polymer, acrylic polymer, starch compound, water-soluble polymer such as polysaccharide, high-purity bentnite, 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.

As an auxiliary agent for preventing caking and promoting disintegration, for example, polysaccharides such as starch, alginic acid, mannose, and galactose, polyvinylpyrrolidone, fumed silica (white carbon), ester gum, petroleum resin, sodium tripolyphosphate, etc. 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.

Further, 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 in 100 parts by weight of the agricultural and horticultural fungicide of the present invention, for example. In the case of powders, granules, emulsions or wettable powders, 0.01 to 50 parts by weight (0.01 to 50% by weight based on the total weight of the agricultural and horticultural fungicides) is appropriate.

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 disease, growth condition of crop, tendency of disease occurrence, 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, dilute it to an appropriate concentration and spray it, or apply it 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, expanding the optimum control period, or 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 present invention is not limited thereto.

Other agricultural and horticultural fungicides used for this purpose include, for example, aureofungin, azaconazole, azithiram, acypetacs, acibenzolar, acibenzolar-S- methyl, azoxystrobin, anilazine, amisulbrom, ampropylfos, ametoctradin, allyl alcohol, aldimorph, ambam, Isotianil, isovaledione, isopyrazam, isofetamid, isoprothiolane, ipconazole, iprodione, iprodione, iprovalicarb, iprovalicarb Iminoctadine, iminoctadine-albesilate, iminoctadine-triacetate, imibenconazole, uniconazole, uniconazole-P, echlomole 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, cyclafuramid, cyclocymet, dichlozoline, diclobutrazole. , Dichlofluanid, cycloheximide, dichromezine, dichloran, dichlorophen, dichlone, disulfiram, ditalimfos, dithianon (Diniconazole), diniconazole M (diniconazole-M), zineb, dinocap, dinocton, dinosulfon, dinoterbon, dinobuton, dinopenton, dipymet ), Dipyrithione, diphenylamine, diphenoconazole, cyflufenamid, diflumetorim, cyproconazole, cyprodinil, cyprodinil, cyprofuram (Simeconazole), dimethirimol, dimethomorph, cymoxanil, dimoxystrobin, ziram, silthiofam, streptomycin, spiroxamine, 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, nitrothal-isopropyl , Nuarimol, copper nonylphenol sulfonate, halacrinate, validamycin, valifenalate, harpin protein, picarbutrazox, bixaphen ( bixafen), picoxystrobin, picobenzamide, bithionol, bitertanol, hydroxyisoxazole, hydroisoxazole-potassium, binapacryl, Biphenyl, piperalin, hymexazol, pyraoxystrobin, pyracarbolid, pyraclostrobin, pyraziflumid, pyrazophos, pyramettrobin ), Pyriofenone, pyridinitril, pydiflumetofen, pydiflumetofen, pyrisoxazole, pyrifenox, pyribencarb, pyrimethanyl Pyroxychlor, pyroxyfur, pyroquilon, vinclozolin, Famoxadone, fenapanil, fenamidone, fenaminosulf, fenaminstrobin, fenarimol, fenitropan, 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, flutolanil flutriafol), furfural, furmecyclox, flumetover, flumorph, professional Kinazid, prochloraz, procymidone, prothiocarb, prothioconazole, propamocarb, propiconazole, propineb, flophanate, flophanate (Probenazole), bromuconazole, hexachlorobutadiene, hexaconazole, hexylthiofos, bethoxazin, benaraxyl, benaraxyl-M, benodanyl-M, benodanyl-M. ), Benomyl, pefurazoate, benquinox, penconazole, benzamorf, pencicuron, benzohydroxamic acid, benzovindiflupyr, benzallon (Bentaluron), benozole (benthiazole), benthiavalicarb-isopropyl, penthiopyrad, penflufen, boscalid, phosdiphen, fosetyl, fosetyl aluminum ( fosetyl-Al), polyoxins, polyoxorim, polycarbamate, folpet, formaldehyde, machine oil, maneb, mancozeb, mandipropamide (Mandipropamid), mandestrobin, microzoline (myclozolin), microbutanil (myclobutanil), mildiomycin (m) ildiomycin), milneb, mecarbinzid, methasulfocarb, metazoxolon, metam, metam-sodium, metalaxyl, metalaxyl- M), metiram, methyl isothiocyanate, methyldinocup, metconazole, metsulfovax, methfuroxam, metomirostrobin, metrominostrobin. metrafenone), mepanipyrim, mefenoxam, meptyldinocap, mepronil, mebenil, iodomethane, rabenzazole, methyl bromide , Inorganic bactericides such as benzalkonium chloride, basic copper chloride, basic copper sulfate, silver metallic silver, sodium hypochlorote , Cupric hydroxide, wettable sulfur, calcium polysulfide, potassium hydrogen carbonate, sodium hydrogen carbonate, inorganic sulfur (sodium hydrogen carbonate) Copper compounds such as sulfur, copper sulfate anhydride, nickel dimethyldithiocarbamate, 8-hydroxyquinoline copper, zinc sulfate, copper sulphate pentahydrate Illustrate (copper sulfate pentahydrate) etc. Can be done.

Agricultural and horticultural insecticides, acaricides, and nematode insecticides used for the same purpose include, for example, 3,5-xylylmethylcarbamate (XMC), Bacillus thuringiensis aizawai, Bacillus thuringiensis israelensis, Bacillus thuringiensis japonensis, Bacillus thuringiensis thuringiensis tenebrionis, Bacillus thuringiensis-produced crystalline protein toxins, BPMC, Bt toxin insecticidal compounds, CPCBS (chlorfenson), DCIP (dichlorodiisopropyl ether), D-D (1,3-Dichloropropene), DDT, NAC, O-4-dimethylsulfamoylphenyl O, O-diethylphosphorothioate (DSP), O-ethylO-4-nitrophenylphenylphosphonothioate (EPN), tripropylisocyanurate (TPIC), acrinathrin, azadirachtin, azinphos-methyl, acequinosyl (acequinocyl), acetamiprid, acetoprole, acephate, abamectin, afidopyropen, avermectin-B, amidoflumet, amitraz, alanical carb, Aldicarb, aldoxycarb, aldrin, alpha-endosulfan, alpha-cypermethrin, albendazole, allethrin, isazofos, Isamidofos, isoamidofos, isoxathio n), isofenphos, isoprocarb (MIPC), empilon-metofluthrin, empilon-momfluorothrin, ivermectin, imicyafos, imidac1oprid, imidac1oprid, imiprotrin (imiprothrin), indoxa Esfenvalerate, ethiofencarb, ethion, ethiprole, etoxazole, ethofenprox, ethoprophos, etrimfos, emamectin Emamectin-benzoate, endosulfan, empentrin, oxamyl, oxydemeton-methyl, oxydeprofos (ESP), oxibendazole, oxfenda Oxfendazole, Potassium oleate, sodium oleate, cadusafos, kappa-bifenthrin, cartap, carbary1, carbosulfan, carbofuryl ), Gamma-cyhalothrin, xylylcarb, quinalphos, kinoprene, chinomethionat, cloethocarb, clothianidin, clofentezine, clofentezine (chromafenozide), chlorantraniliprole, chlorethoxyfos, chlo. rdimeform), chlordane, chlorpyrifos, chlorpyrifos-methyl, chlorphenapyr, chlorfenson, ch1orfenvinphos, chlorfluazuron, Chlorpyrifos, chlorobenzoate, chloroprallethrin, kelsen (dicofol), salithion, cyhalodiamide, cyanophos (CYAP), diafenthiuron, diamidafos, cyan Cyantraniliprole, theta-cypermethrin, dienochlor, cyenopyrafen, dioxabenzofos, diofenolan, sigma-cypermethrin , Dichlofenthion (ECP), cycloprothrin, dichlorvos (DDVP), disulfoton, dinotefuryl, cyhalothrin, cyphenothrin, cyphenothrin diflubenzuron), cyflumetofen, diflovidazin, cyhexatin, cypermethrin, dimethylvinphos, dimethoate, dimefluthrin, dimefluthrin, silafluthrin , Spinettoram, spinosad , Spirodiclofen, spirotetramat, spiromesifen, sulfluramid, sulprofos, sulfoxaflor, zeta-cypermethrin, diadinone (diazinon), tau-fluvalinate, dazomet, thiacloprid, thiamethoxam, tioxazafen, thiodicarb, thiocyclam, thiosultap, thiosultap thiosultap-sodium, thionazin, thiometon, deet, dieldrin, tetrach1orvinphos, tetradifon, tetraniliprole, tetramethylfluthrin, tetramethylfluthrin (tetramethylfluthrin) tetramethrin, tebupirimfos, tebufenozide, tebufenpyrad, tefluthrin, teflubenzuron, demeton-S-methyl, temefos, delta , Temefos, tralopyril, tralomethrin, transfluthrin, triazamate, triazuron, trichlamide, trichlorphon: DEP, triflumezopyrim, triflumezopyrim ), Tolfenpyrad, naled (BRP), nithiazine, nitenp yram, novaluron, noviflumuron, hydroprene, vaniliprole, vamidothion, parathion, parathion-methyl, halfenprox, Halofenozide, bistrifluron, bisultap, hydramethylnon, hydroxypropylstarch, binapacryl, pyflubumide, bifenazate, bifenthrin bifenthrin, pymetrozine, pyraclorfos, pyrafluprole, pyridafenthion, pyridaben, pyridalyl, pyrifluquinazon, pyrifluquinazon, pyriprole ), Pirimicarb, pyrimidifen, pyriminostrobin, pyrimiphos-methy1, pyrethrins, fiproni1, fenazaquin, fenamiphos, fenamiphos, phenisobromolate (fenitrothion: MEP), fenoxycarb, fenothiocarb, phenothrin, fenobucarb, fensulfothion, fenthion (MPP), phenthoate (PAP), fenvalerate (fenvalerate), fenpyroximate, fenpr opathrin, fenbendazole, fosthiazate, formetanate, butathiofos, buprofezin, furathiocarb, prallethrin, fluacrypyrim, fluacrypyrim, fluacrypyrim (fluazinam), fluazuron, fluensulfone, fluxametamide, flucycloxuron, flucythrinate, fluvalinate, flufiprole, flupyradifurone, flupyrazofos, flupyrazofos, flupyrazofos ), Flufenoxystrobin, flufenoxuron, flufenzine, flufenoprox, fluproxyfen, flubrocythrinate, fluhexafon, flubendiamide, flumethrin ), Flurimfen, prothiofos, protrifenbute, flonicamid, propaphos, propargite (BPPS), profenofos, profluthrin, propokislu propoxur: PHC, flometoquin, bromopropylate, beta-cyfluthrin, hexaflumuron, hexythiazox, heptafluthrin, heptenophos, permethrin, permethrin ), Bendiocarb, Ben Sultap (bensu1tap), benzoximate, benfuracarb, phoxim, phosalone, fosthiazate, fosthietan, phosphamidon, phosphocarb, phosmet : PMP), polynactins, formetanate, formothion, phorate, machine oil, malathion, milbemycin, milbemycin-A , Milbemectin, mecarbam, mesulfenfos, methomyl, metaldehyde, metaflumizone, metamidophos, metam-ammonium, metam sodium (metam-ammonium) metam-sodium, methiocarb, methidathion (DMTP), methylisothiocyanate, methylneodecanamide, methylparathion, metoxadiazone, methoxychlor, methoxyphenodide. methoxyfenozide), metoflutrin, metoprene, metolcarb, meperfluthrin, mevinphos, monocrotophos, monosultap, momfluorothrin, lambda-cyhalothrin Rianodine, lufenuron, rescalure, resmethrin, Lepimectin, rotenone, levamisolhydrochloride, fenbutatin oxide, morantel tartarate, methyl bromide, tricyclohexyltin hydroxide (cyhexatin), lime nitrogen Examples thereof include (calcium cyanamide), lime sulfur, sulfur (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, acetamide Acetochlor, atrazine, atraton, anisuron, anilofos, aviglycine, abscisic acid, amiclabazone, amidosulfuron, amidolfuron (Amitrole), aminocyclopyrachlor, aminopyralid, amibuzin, amiprophos-methyl, ametridione, ametridione, ametridine, alachlor, aridochlor (amitrole), aminocyclopyrachlor, aminopyralid, amibuzin, amiprophos-methyl allidochlor, alloxydim, alorac, iofensulfuron, isouron, isocarbamid, isoxachlortole, isoxapyrifop, isoxaflu Thor (isoxaflutole), isoxaben, isoxaben, isocil, isonorruron, isoproturon, isopropalin, isopolinate, isomethiozin, inabenfide, ipadine ip , Ipf Ipfencarbazone, iprymidam, imazaquin, imazapic, imazapyr, imazamethapyr, imazamethabenz, imazamethabenz, imazamethabenz-methyl , Imazethapyr, imazosulfuron, indaziflam, indanofan, indolebutyric acid, uniconazole-P, eglinazine, esprocarb (Ethhametsulfuron), ethametsulfuron-methyl, ethalfluralin, ethiolate, ethychlozate ethyl, ethidimuron, etinofen, etenofen, ethephon Ethylfuron, ethoxyfen, etnipromid, ethofumesate, etobenzanid, epronaz, erbon, endothal, oxadiazon, oxadiazon. oxadiargyl, oxaziclomefone, oxasulfuron, oxapyrazon, oxyfluorfen, oryzalin, orthosulfamuron, orbencarb, cafenrole Benjichlor, carfendichlor, carfentrazone, carfen Carfentrazone-ethyl, karbutilate, carbetamide, carboxazole, quizalofop, quizalofop-P, quizalofop-ethyl, xila Croll (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 (chlormequat) chloreturon, chloroxynil, chloroxuron, chloropon, saflufenacil, cyanazine, cyanatryn, di-allate, diuron, diethamquat Dicamba, cycluron, cycloate, cycloxydim, diclosulam, cyclosulfamuron, cyclopyrimorate, dichlorprop, dicloprop- P (dichlorprop-P), dichlobenil, dichlobenil, diclohop-methyl, dichlormate, dichloralurea, diquat, cisanilide, disul ), Siduron, dithiopyr, dinitramine, cinidon-ethyl, dinosam, cinosulfuron, dinoseb, dinoterb, dinoterb, dinophenate (Dinoprop), cyhalofop-butyl, diphenamid, difenoxuron, difenopenten, difenzoquat, cybu tryne, cyprazine, cyprazole, diflufenican, diflufenzopyr, dipropetryn, cypromid, cyperquat, gibberellin, simazine , Dimexano, dimethachlor, dimedazon, dimethametryn, dimethenamid, simetryn, simeton, dimepiperate, dimepiperate, dimepiperate, dimepiperate , Swep, sulglycapin, sulcotrione, sulfallate, sulfentrazone, sulfosulfuron, sulfometuron, sulfometuron-methyl. ), Sekbumeton, sethoxydim, sebuthylazine, terbacil, daimuron, dazomet, dalapon, thiazafluron, thiazopyr ), Thiencarbazone, thiencarbazone-methyl, tiocarbazil, tioclorim, thiobencarb, thidiazimin, thidiazuron, thifensulfuron Fencesulfuron-methyl, desmedipham, desmetryn, tetrafl uron, thenylchlor, tebutam, tebuthiuron, terbumeton, tepraloxydim, tefuryltrione, tembotrione, delachlor, terbacil. ), Terbucarb, terbuchlor, terbuthylazine, terbutryn, topramezone, tralkoxydim, 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, burban (b) arban), paclobutrazol, paraquat, parafluron, haloxydine,
Halauxifen, haloxyfop, haloxyfop-P, haloxyfop-methyl, halosafen, halosulfuron, halosulfuron-methyl, picrolam (Picloram), picolinafen, bicyclopyrone, bispyribac, bispyribac-sodium, pydanon, pinoxaden, bifenox, piperophos, Hymexazol, pyraclonil, pyrasulfotole, pyrazoxyfen, pyrazosulfuron, pyrazosulfuron-ethyl, pyrazolate, pyranaphos, bilanafos Ethyl (pyraflufen-ethyl), pyriclor, pyridafol, pyrithiobac, pyrithiobac-sodium, pyridate, pyriftalid, pyribticarb, pyribenzoxim ), Pyrimisulfan, primisulfuron, pyriminobac-methyl, pyroxasulfone, pyroxsulam, fenasulam, phenisopham, phenisopham fenuron), fenoxasulfone, fenoxaprop, fenoxaprop-P, fenoxaprop-ethyl, fe Nothiol (phenothio1), phenoprop, phenobenzuron, fenquinotrione, fenthiaprop, fenteracol, fentrazamide, phenmedipham, Phenmedipham-ethyl, butachlor, butafenacil, butamifos, buthiuron, buthidazole, butylate, buturon, butenachlor, Butroxydim, butralin, flazasulfuron, flamaprop, furyloxyfen, prynachlor, primisulfuron-methyl, fluazifop , Fluazifop-P, fluazifop-butyl, fluazolate, fluroxypyr, fluothiuron, fluometuron, fluoroglycofen, fluloculoridone (Flurochloridone), fluorodifen, fluoronitrofen, fluoromidine, flucarbazone, flucarbazone-sodium, fluchloralin, flucetosulfuron, Fluthiacet, fluthiacet-methyl, flupyrsulfuron, flufenacet, flufen ican, flufenpyr, flupropacil, flupropanate, flupoxam, flumioxazin, flumiclorac, flumiclorac-pentyl, flumiclorac-pentyl flumipropyn, flumezin, fluometuron, flumetsulam, fluridone, flurtamone, fluroxypyr, pretilachlor, proxan, proxan, proxan procyazine, prodiamine, prosulfalin, prosulfuron, prosulfocarb, propaquizafop, propachlor, propazine, propanil ), Propyzamide, propisochlor, prohydrojasmon, propyrisulfuron, propham, profluazol, profluralin, prohexadione calcium ( prohexadione-calcium, propoxycarbazone, propoxycarbazone-sodium, profoxydim, bromacil, brompyrazon, prometryn, prometon, bromoxynil. ), Bromofenoxim, bromobutide, bromobonil, florasulam, florpyroxyfe Florpyrauxifen, hexachloroacetone, hexazinone, petthoxamid, benazolin, penoxsulam, pebulate, beflubutamid, vernolate, perfluidone. ), Bencarbazone, benzadox, benzipram, benzylaminopurine, benzthiazuron, benzfendizone, bensulide, bensulfuron-methyl. ), Benzoylprop, benzobicyclon, benzofenap, benzofluor, bentazone, pentanochlor, benthiocarb, pendimethalin () pendimethalin, pentoxazone, benfluralin, benfuresate, fosamine, fomesafen, foramsulfuron, forchlorfenuron, hydrazide maleate ), Mecoprop, mecoprop-P, medinoterb, mesosulfuron, mesosulfuron-methyl, mesotrione, mesoprazine, mesoprotryne Metazachlor, methazole, metazosulfuron, metabenzthiazuron ), Metamitron, metamifop, metam, metalpropalin, methiuron, methiozolin, methiobencarb, methyldymron, metoxuron. , Metosulam, metsulfuron, metsulfuron-methyl (metsu1furon-methy1), metflurazon, metobromuron, metobensuron, metobenzuron, metometon, methrometon, methrometon , Mepiquat-chloride, mefenacet, mefluidide, monalide, monisouron, monuron, monochloroacetic acid, monochloroacetic acid, monolinuron molinate, morfamquat, iodosulfuron, iodosulfuron-methyl-sodium, iodobonil, iodomethane, lactofen, linuron, Examples thereof include rimsulfuron, lenacil, rhodethanil, calcium peroxide, and methyl bromide.

Examples of biopesticides include nuclear polyhedrosis virus (NPV), granulosis virus (GV), cytoplasmic polyhedrosis virus (CPV), and insect poxvirus (Entomopoxivirus). Virus preparations such as EPV, Monochromesporium phymatophagum, Steinernema carpocapsae, Steinernema kushidai, Pasteuria penetrans Bactericidal agents such as microbial pesticides used as insecticides, 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, a biopesticide used as a herbicide such as Xanthomonas campestris, and the like.

Further, as biopesticide, for example, Onshitsuyakobachi (Encarsiaformosa), Aphidius colemani, Cecidomyiidae (Aphidoletesaphidimyza), Isaeahimekobachi (Diglyphusisaea), Hamoglycomayu bee (Dacnusasib) 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-icosen-10-on, 14-methyl- It can also be used in combination with a pheromone agent such as 1-octadecene.

The following is an example of typical examples of the method for producing the compound of the present invention, but the method for producing the compound of the present invention is not limited thereto.

　５‐[５‐（トリフルオロメチル）‐１，２，４‐オキサジアゾール‐３‐イル]チオフェン‐２‐カルボアルデヒド（０．３５ｇ，１．４ｍｍｏｌ）をアルゴン雰囲気下、クロロホルム（１０ｍＬ）に溶かし、ホルムアミド（０．０７６ｇ，１．７ｍｍｏｌ）、チタン（ＩＶ）イソプロポキシド（０．７２ｇ，２．５ｍｍｏｌ）を加え、室温で２４時間静置した。その後、酢酸エチルで希釈し、シリカゲルを加え２５分間攪拌した後、減圧濃縮した。得られ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で、表題の化合物（０．０６ｇ，０．１９ｍｍｏｌ）を得た。
収率：１４％
物性値：融点１０１‐１０２℃ Manufacturing Example 1
Preparation of N- (isopropoxy {5- [5- (trifluoromethyl) -1,2,4-oxadiazole-3-yl] thiophen-2-yl} methyl) formamide (Compound 1-4)

5- [5- (Trifluoromethyl) -1,2,4-oxadiazole-3-yl] thiophen-2-carbaldehyde (0.35 g, 1.4 mmol) in chloroform (10 mL) under an argon atmosphere. After melting, formamide (0.076 g, 1.7 mmol) and titanium (IV) isopropoxide (0.72 g, 2.5 mmol) were added, and the mixture was allowed to stand at room temperature for 24 hours. Then, the mixture was diluted with ethyl acetate, silica gel was added, the mixture was stirred for 25 minutes, and then concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to give the title compound (0.06 g, 0.19 mmol).
Yield: 14%
Physical characteristics: Melting point 101-102 ° C

 
　５‐ブロモチオフェン‐２‐カルボアルデヒド（１３ｇ，６８ｍｍｏｌ）をトルエン（１２０ｍＬ）に溶かし、エチレングリコール（１７ｇ，２７２ｍｍｏｌ）、ｐ‐トルエンスルホン酸一水和物　（１．３ｇ，６．８ｍｍｏｌ）を加え、ディーンスターク装置を用いて水を除去しながら４時間加熱還流した。反応終了後、室温に戻し、飽和炭酸水素ナトリウム水溶液を加えて反応を停止し、酢酸エチルで抽出した。有機層を飽和食塩水で洗浄後、硫酸ナトリウムで乾燥し、減圧濃縮することで、表題の化合物（１７ｇ，７１ｍｍｏｌ）を得た。
収率：１０４％
物性値：屈折率１．３４３２（２４．６） Reference example 1
Production of 2- (5-bromothiophene-2-yl) -1,3-dioxolane

5-Bromothiophene-2-carbaldehyde (13 g, 68 mmol) is dissolved in toluene (120 mL), ethylene glycol (17 g, 272 mmol) and p-toluenesulfonic acid monohydrate (1.3 g, 6.8 mmol) are added. , Heat refluxed for 4 hours while removing water using a Dean-Stark apparatus. After completion of the reaction, the temperature was returned to room temperature, saturated aqueous sodium hydrogen carbonate solution was added to stop the reaction, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over sodium sulfate, and concentrated under reduced pressure to give the title compound (17 g, 71 mmol).
Yield: 104%
Physical property value: Refractive index 1.3432 (24.6)

　２‐（５‐ブロモチオフェン‐２‐イル）‐１，３‐ジオキソラン（１７ｇ，７１ｍｍｏｌ）をＤＭＡ（３５ｍＬ）に溶かし、シアン化銅（Ｉ）（７．０ｇ，７８ｍｍｏｌ）を加え、１５０℃で５．５時間加熱攪拌した。反応終了後、室温に戻し、セライトろ過した。４％アンモニア水溶液を加えて反応を停止し、酢酸エチルで抽出した。有機層を飽和食塩水で洗浄後、硫酸ナトリウムで乾燥し、減圧濃縮した。得られ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で、表題の化合物（６．５ｇ，３６ｍｍｏｌ）を得た。
収率：５０％
物性値：屈折率１．３４５４（２３．０） Reference example 2
Preparation of 5- (1,3-dioxolane-2-yl) thiophene-2-carbonitrile

2- (5-Bromothiophene-2-yl) -1,3-dioxolane (17 g, 71 mmol) is dissolved in DMA (35 mL), copper (I) cyanide (7.0 g, 78 mmol) is added, and the temperature is 150 ° C. The mixture was heated and stirred for 5.5 hours. After completion of the reaction, the temperature was returned to room temperature and the mixture was filtered through cerite. The reaction was stopped by adding a 4% aqueous ammonia solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain the title compound (6.5 g, 36 mmol).
Yield: 50%
Physical property value: Refractive index 1.3454 (23.0)

　５‐（１，３‐ジオキソラン‐２‐イル）チオフェン‐２‐カルボニトリル（６．５ｇ，３６ｍｍｏｌ）をエタノール（７０ｍＬ）に溶かし、トリエチルアミン（５．４ｇ，５４ｍｍｏｌ）、ヒドロキシルアミン塩酸塩（３．７ｇ，５４ｍｍｏｌ）を加え、加熱還流下３時間撹拌した。その後、水を加え、減圧濃縮によりエタノールを除去し、酢酸エチルで抽出した。有機層を飽和食塩水で洗浄後、硫酸ナトリウムで乾燥し、減圧濃縮した。得られ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で、表題の化合物（５．１ｇ，２４ｍｍｏｌ）を得た。
収率：６６％
物性値：融点１３１‐１３３℃ Reference example 3
Production of (Z) -5- (1,3-dioxolane-2-yl) -N'-hydroxythiophene-2-carboxyimidazole

5- (1,3-Dioxolane-2-yl) thiophene-2-carbonitrile (6.5 g, 36 mmol) was dissolved in ethanol (70 mL), triethylamine (5.4 g, 54 mmol), hydroxylamine hydrochloride (3. 7 g, 54 mmol) was added, and the mixture was stirred under heating under reflux for 3 hours. Then, water was added, ethanol was removed by concentration under reduced pressure, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain the title compound (5.1 g, 24 mmol).
Yield: 66%
Physical characteristics: Melting point 131-133 ° C

　（Ｚ）‐５‐（１，３‐ジオキソラン‐２‐イル）‐Ｎ’‐ヒドロキシチオフェン‐２‐カルボキシイミダミド（４．４ｇ，２１ｍｍｏｌ）をクロロホルム（５０ｍＬ）に溶かし、ピリジン（９．７ｇ，１２４ｍｍｏｌ）、トリフルオロ酢酸無水物（８．７ｇ，４１ｍｍｏｌ）を加え、室温で４．５時間攪拌した。その後、水を加え、クロロホルムで抽出した。有機層を飽和食塩水で洗浄後、硫酸ナトリウムで乾燥し、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で、表題の化合物（４．５ｇ，１５ｍｍｏｌ）を得た。
収率：７４％
物性値：融点４４‐４５℃
参考例５
５‐[５‐（トリフルオロメチル）‐１，２，４‐オキサジアゾール‐３‐イル]チオフェン‐２‐カルボアルデヒドの製造

　３‐［５‐（１，３‐ジオキソラン‐２‐イル）チオフェン‐２‐イル］５‐（トリフルオロメチル）‐１，２，４‐オキサジアゾール（４．４ｇ，１５ｍｍｏｌ）を１，４‐ジオキサン４５（ｍＬ）に溶かし、２Ｍ塩酸水溶液（４５ｍｌ，９０ｍｍｏｌ）を加え、室温で４時間攪拌した。その後、飽和炭酸水素ナトリウム水溶液を加え、酢酸エチルで抽出した。有機層を飽和食塩水で洗浄後、硫酸ナトリウムで乾燥し、減圧濃縮することで、表題の化合物（３．７ｇ，１５ｍｍｏｌ）を得た。
収率：９９％
物性値：融点５６‐５７℃ Reference example 4
3- [5- (1,3-dioxolane-2-yl) thiophene-2-yl] 5- (trifluoromethyl) -1,2,4-oxadiazole

(Z) -5- (1,3-dioxolane-2-yl) -N'-hydroxythiophene-2-carboxyimidazole (4.4 g, 21 mmol) was dissolved in chloroform (50 mL) and pyridine (9.7 g, 9.7 g, 124 mmol) and trifluoroacetic anhydride (8.7 g, 41 mmol) were added, and the mixture was stirred at room temperature for 4.5 hours. Then, water was added and the mixture was extracted with chloroform. The organic layer was washed with saturated brine, dried over sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give the title compound (4.5 g, 15 mmol).
Yield: 74%
Physical characteristics: Melting point 44-45 ° C
Reference example 5
Production of 5- [5- (trifluoromethyl) -1,2,4-oxadiazole-3-yl] thiophene-2-carbaldehyde

3- [5- (1,3-dioxolane-2-yl) thiophene-2-yl] 5- (trifluoromethyl) -1,2,4-oxadiazole (4.4 g, 15 mmol) 1,4 -Dissolved in 45 (mL) of dioxane, 2M aqueous hydrochloric acid solution (45 ml, 90 mmol) was added, and the mixture was stirred at room temperature for 4 hours. Then, saturated aqueous sodium hydrogen carbonate solution was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over sodium sulfate, and concentrated under reduced pressure to give the title compound (3.7 g, 15 mmol).
Yield: 99%
Physical characteristics: Melting point 56-57 ° C

Examples of the pharmaceutical product are shown below, but the pharmaceutical product containing the compound of the present invention is not limited thereto. In the pharmaceutical product 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 lignin sulfonate calcium 5 parts or more are uniformly mixed, kneaded with an appropriate amount of water, granulated and dried. Use as granules.

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

 
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％ Test example 1. Bactericidal effect test against 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 is diluted with water to a predetermined concentration and has a diameter of 6 cm. Soybeans (variety: Enrei, 2 leaf stage) raised in seedlings were sprayed with foliage at a rate 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 (Phakopsora pachyrhizi) is 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.

Judgment criteria 0: Control value is 9% or less 1: Control value is 10 to 19%
2: Control price is 20-29%
3: Control price is 30-39%
4: Control price 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, 1-2, 1-3, 1-4, 1-7 and 1-10 have a treatment concentration of 50 ppm and are criteria for determination. It showed an effect of 8 or more.

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.

Claims (6)

General formula (I)

{In the formula, R ¹ is
(a1) Hydrogen atom;
(a2) (C ₁ -C ₆ ) Alkyl group;
(a3) (C ₂ -C ₆ ) alkenyl group;
(a4) (C ₂ -C ₆ ) Alkynyl group;
(a5) (C ₃ -C ₆ ) Cycloalkyl group;
(a6) Halo (C1 _{- C6} ) alkyl group;
(a7) Halo (C2 _- C- ₆ ) alkenyl group;
(a8) Halo (C2 _- C- ₆ ) alkynyl group; or
(a9) Shows a halo (C ₃ -C ₈ ) cycloalkyl group.
R ² is
(b1) Hydrogen atom;
(b2) (C ₁ -C ₆ ) Alkyl group;
(b3) (C ₂ -C ₆ ) Alkenyl group;
(b4) (C ₂ -C ₆ ) Alkynyl group;
(b5) (C ₃ -C ₆ ) Cycloalkyl group;
(b6) Halo (C- _{1 -} C6) alkyl group;
(b7) Halo (C2 _- C- ₆ ) alkenyl group;
(b8) Halo (C2 _- C- ₆ ) alkynyl group; or
(b9) Shows a halo (C ₃ -C ₈ ) cycloalkyl group.
R ³ is
(c1) Hydrogen atom;
(c2) (C ₁ -C ₆ ) Alkyl group;
(c3) (C2 _- C- ₆ ) alkenyl group;
(c4) (C2 _- C- ₆ ) alkynyl group;
(c5) (C ₃ -C ₆ ) Cycloalkyl group;
(c6) (C ₁ -C ₆ ) Alkylcarbonyl group; or
(c7) (C ₁ -C ₆ ) Shows an alkoxycarbonyl group.
X ¹ and X ² are independent of each other
(e1) Hydrogen atom;
(e2) Halogen atom;
(e3) Cyano group;
(e4) Nitro group;
(e5) (C ₁ -C ₆ ) Alkyl group;
(e6) (C ₃ -C ₆ ) Cycloalkyl group;
(e7) (C ₁ -C ₆ ) Alkoxy group;
(e8) Halo (C- ₁ -C- ₆ ) alkyl group;
(e9) Halo (C1-C _{- 6} ) alkoxy group;
(e10) Halo (C ₃ -C ₆ ) cycloalkyl group;
(e11) (C ₁ -C ₆ ) Alkylthio group;
(e12) (C ₁ -C ₆ ) Alkyl sulfinyl group;
(e13) (C ₁ -C ₆ ) Alkylsulfonyl group;
(e14) Halo (C- ₁ -C- ₆ ) alkylthio group;
(e15) Halo (C1-C _{- 6} ) alkylsulfinyl group; or
(e16) Shows a halo (C1-C _{- 6} ) alkylsulfonyl group. }
A compound represented by or a salt thereof. R ¹ is
(a2) (C ₁ -C ₆ ) Alkyl group; or
(a5) (C ₃ -C ₆ ) It is a cycloalkyl group and
R ² is
(b1) It is a hydrogen atom and
R ³ is
(c1) It is a hydrogen atom and
X ¹ and X ²
(e1) The compound according to claim 1 or a salt thereof, which is a hydrogen atom. R ¹ is
(a2) (C ₁ -C ₆ ) The compound according to claim 1 or 2, or a salt thereof, which is an alkyl group. A fungicide for agriculture and horticulture, which comprises the compound according to any one of claims 1 to 3 or salts thereof as an active ingredient. A method for controlling plant diseases, which comprises treating a plant or soil with an effective amount of the agricultural and horticultural fungicide according to claim 4. Use of the compound according to any one of claims 1 to 3 or a salt thereof as a disinfectant for agriculture and horticulture.