JP2000159610A - Plant disease control agent for agriculture and horticulture and new isooxazole carboxylic acid derivative - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain the subject agent having high control effects against plant diseases such as rice blast and rice sheath blight without giving chemical damages to plants by adding a specific isooxazole carboxylic acid derivative as an active ingredient. SOLUTION: This plant disease control agent for agriculture and horticulture contains an isooxazole carboxylic acid derivative of formula I (R1 is a halogen, a lower haloalkyl or the like; R2 is H, a halogen or the like; X is O, S or the like; R3, R4 are each H, a lower alkyl or the like) (for example, 3- trifluoromethylisooxazole-5-carboxylic acid) as an active ingredient. The compound of formula I is obtained, for example, by reacting a compound of formula II (R11 is hydroxymethyl or the like) (for example, 3-trifluoromethylisooxazole-5- methanol) with an oxidizing agent such as potassium permanganate. When sprayed on stems and leaves, the agent is preferably applied in an amount of 30-1,000 liter per 10 are an a diluted solution containing the active ingredient in a concentration of 10-500 ppm.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

TECHNICAL FIELD The present invention relates to a plant disease controlling agent for agricultural and horticultural use containing an isoxazolecarboxylic acid derivative having an action of controlling plant disease fungi as an active ingredient. The present invention also relates to a novel isoxazole carboxylic acid derivative having control activity against plant diseases. Therefore, the present invention is useful in the chemical industry as well as in agriculture, especially in the field of agrochemical manufacturing.

[0002]

2. Description of the Related Art (i) Until now, isoxazole-5
The following compounds are known as compounds belonging to the carboxylic acid amide derivative. (1) Japanese Unexamined Patent Publication No. 1-230563 describes a carboxylic acid amide compound having a cyano group represented by the following general formula (A), R _1, R ₂ is a hydrogen atom, the compounds of the alkyl group It is described as a fungicide having activity to control downy mildew and plague. X and Y: one is a carbon atom, the other is an oxygen atom R ₁ , R ₂ : hydrogen atom, lower alkyl group, halogen atom,
Phenyl group R ₃ : alkyl group, alkenyl group, haloalkenyl group, phenyl group and the like.

(2) JP-A-63-119463 describes that a compound represented by the following general formula (B) has a fungicidal activity against cucumber downy mildew and the like. B: lower alkoxy group, haloalkoxy group, 1-pyrazolyl group and the like.

Y, W: hydrogen atom, lower alkyl group, acetyl group, etc. A: heterocycle of the following formula Such.

(3) JP-A-56-155872 discloses that a compound represented by the following general formula (C) has a fungicidal activity against tomato blight and the like. R ₁ : C ₁ -C ₃ alkyl group R ₂ : hydrogen atom, C ₁ -C ₃ alkyl group, halogen atom R ₄ : hydrogen atom, substituted alkyl group, etc. R ₅ , R ₆ , R ₇ : hydrogen atom, methyl group .

(4) JP-A-56-59765 discloses that a compound represented by the following general formula (D) has a fungicidal activity against wheat powdery mildew, tomato late blight, grape downy mildew and the like. Have been. R ₁ : methyl group, ethyl group, chlorine atom R ₂ : hydrogen atom, methyl group, ethyl group, halogen atom R ₃ : methyl group, ethyl group R ₄ : hydrogen atom, methyl group, ethyl group.

(5) German Offenlegungsschrift No. 3414951 describes that a compound represented by the following general formula (E) has a fungicidal activity against tomato blight and the like. R ₁ : hydrogen atom, methyl group, ethyl group, chloromethyl group.

(6) German Patent Publication No. 3506814 discloses that a compound represented by the following general formula (F) has a fungicidal activity in controlling diseases such as wheat powdery mildew and downy mildew. I have. A: C ₂ ~C ₁₀ alkyl group B: a lower alkyl group, C ₅ -C ₈ cycloalkyl group R _1: a hydrogen atom, a substituted phenyl group R _3: a lower alkyl group, and a substituted phenyl group m, n: 0, One.

(7) EP-A-761654 discloses that
It is described that the compound of the following general formula (G) has herbicidal activity. Y: hydrogen atom, halogen atom, substituted alkyl group, etc. W: substituted alkyl group, alkenyl group, etc. X: O, S Z: substituted C ₁ -C ₄ alkylene group R ₁ : substituted alkyl group, substituted acyl group, etc. R ₂ : Substituted aryl group, heteroaryl group and the like.

(8) JP-A-2-28166 describes a compound represented by the following general formula (H) as a herbicide or a synthetic intermediate thereof. X: oxygen atom, sulfur atom R ₁ : hydrogen atom, substituted alkyl group, substituted phenyl group, etc. R ₃ , R ₄ : hydrogen atom, lower alkyl group, substituted phenyl group, etc.

(9) JP-T-2-500365 describes that a compound represented by the following general formula (J) has a recognition assisting action. R: hydrogen atom, lower alkyl group, halogen atom, etc. R ₁ : hydroxyl group, alkoxy group, etc. n: 1, 2.

(10) JP-A-3-206086 describes that a compound represented by the following general formula (K) has activity as a neurokinin antagonist. Z: lower alkyl group, substituted phenyl group, heteroaryl group, or group of the following formula Such as Ar, Ar ': substituted phenyl, thienyl, etc. X: a hydrogen atom X _1: a hydrogen atom, a hydroxyl group Q: hydrogen atom, a lower alkyl group T: R: a hydrogen atom, a methyl _{group, - (CH 2) n -NH} 2 m: 1~3 integer, n: 2 to 6 integer.

(11) JP-A-3-130270, JP-A-5-130270
No. 86039, JP-A-6-505228, JP-A-8-41037
The publication describes that the compound of the following general formula (L) has herbicidal activity. R ₁ : hydrogen, halogen atom, lower alkyl group, etc. R ₂ : formyl group, lower alkoxycarbonyl group, etc. R ₃ : hydrogen atom, haloalkyl group, alkoxyalkyl group, etc. R ₄ : hydrogen atom, hydroxy group, lower alkoxy group, etc. X : Oxygen atom, sulfur atom.

(12) PCT International Publication No. WO 96/16954 describes that compounds of the following general formula (M) have bactericidal activity against tomato late blight, grape downy mildew, cucumber powdery mildew, rice blast and the like. ing. X: oxygen atom, sulfur atom Y: alkyl group, cycloalkyl group, alkenyl group, etc. Z: alkoxycarbonyl group, cyano group, nitro group, etc. A: 5-membered heterocyclic ring, R ₁ : alkyl group, cycloalkyl group, alkenyl group ,
Amino group and the like.

(Ii) The following compounds are known as isoxazolecarboxylic acids and their ester derivatives. (1) JP-B-43-112 discloses a compound represented by the following formula (N) as a 5-carboxylic acid derivative having a hydroxy group at the 4-position. These compounds are described as having fungicidal effects on soil diseases. R ₁ : hydrogen atom, halogen atom, lower alkyl group R ₂ : lower alkoxycarbonyl group, phenyl group and the like.

(2) JP-B-44-31357 describes that a compound represented by the following general formula (O) has activity as a fungicide for controlling soil diseases, strawberry gray mold and the like. R ₁ : hydrogen atom, halogen atom, lower alkyl group R ₂ : lower alkoxycarbonyl group, phenyl group, etc. M: Na, Ca, etc.

(3) Isoxazole-5-carboxylic acid having a substituent at the 3-position and its ester derivative can be prepared by the method of Acta.
m. Scand. Ser. B , B38 , 815 (1984), Biochem. Pharmaco
l. 18 , 569 (1969), Farmaco, Ed.Sci. 41 , 440 (1986), L
iebigs Ann.Chem. 8 , 815 (1993), JP-A-62-501416, J. Heterocycl.Chem. 24 , 43 (1987), Japanese Patent Publication No. 43-1
No. 6382, Ann. 369 , 300 (1909), British Patent No. 1146448, Ist. Lombard Sci. Pt.
94A , 729 (1960), Gazz.Chim.Ital. 91 , 47 (1961), U.S. Pat.No. 3,972,209, U.S. Pat. Publication, JP-A-6-199802, J. Med.Chem. 39 , 2232 (199
6), JP-A-59-137472, Synthesis, 69 (1986), J.
Org. Chem. 26 , 1514 (1961), Journal of Industrial Science, 66 , 1831 (1961).
3), Industrial Science Magazine, 66 , 1838 (1963), Ber. 106 , 3345 (197
3), J. Am. Pharm. Assoc., 42 , 594 (1953), Gazz. Chim.
Ital., 81 , 117 (1951), Arznemittel-Forschung, 24 , 363
(1974), but is not known to have a plant disease controlling effect.

[0018]

In the cultivation of agricultural or horticultural crops, various diseases that have a significant effect on production efficiency are known, such as blast and sheath blight in rice cultivation, fruit trees, vegetables, and so on. Powdery mildew, downy mildew, and gray mold in grain cultivation can be cited as important diseases.

Various fungicides have been used for the diseases caused by these plant pathogens. However, these known drugs conventionally used generate resistant bacteria due to long-term use, and cannot be used because they cannot obtain a sufficient bactericidal effect, or must be used in combination with other drugs to obtain a sufficient bactericidal effect. was there. Therefore, in the field of cultivation of agricultural or horticultural crops,
There has been a demand for the emergence of a novel plant disease controlling compound which has a different chemical structure skeleton from conventional drugs and exhibits a sufficient controlling effect. The present invention seeks to solve the problems associated with the prior art as described above. An object of the present invention is to provide a novel drug that exhibits sufficient plant disease control activity without crossing known drug-resistant bacteria due to a different chemical structure skeleton from conventional drugs.

[0020]

Means for Solving the Problems In order to achieve the above object, the present inventors have synthesized a large number of new or known isoxazole carboxylic acid derivatives whose plant disease controlling activity has not been known so far and synthesized them. We investigated the activity and usefulness of plant disease control. As a result, they have found that isoxazole carboxylic acid derivatives containing a known compound and a novel compound, which are partially represented by the general formula (I) described below, have an excellent plant disease control effect without causing phytotoxicity to plants. Was.

Therefore, the gist of the first invention is that the general formula (I) [In the formula, R ₁ represents a halogen atom, a lower haloalkyl group or a lower haloalkoxy group, R ₂ represents a hydrogen atom,
X represents a halogen atom or a lower alkyl group; X represents an oxygen atom, a sulfur atom, or an NR ₄ group; R ₃ and R ₄ may be the same or different, and each represents a hydrogen atom, a lower alkyl group, a lower alkyl group; An alkenyl group, a lower alkynyl group, or a cycloalkyl group having 3 to 8 carbon atoms which may be substituted with one or more lower alkyl groups, carboxy groups or lower alkoxycarbonyl groups, or lower haloalkyl groups, lower haloalkenyls Group, lower haloalkynyl group, lower alkoxy lower alkyl group, lower alkoxycarbonyl group, carboxy lower alkyl group, lower alkoxycarbonyl lower alkyl group, lower alkylcarbonyl group, lower haloalkylcarbonyl group, lower alkylsulfonyl group, lower haloalkylsulfonyl group, Or unsubstituted Benzoyl group or 1-5 lower alkyl group, a lower alkoxy group, lower haloalkoxy group, lower haloalkyl group, a lower alkoxycarbonyl group, a lower alkylthio group, a lower alkylsulfonyl group,
A benzoyl group substituted with a halogen atom, a cyano group, or an unsubstituted phenylsulfonyl group, or 1 to 5
Lower alkyl group, lower alkoxy group, lower haloalkyl group, lower haloalkoxy group, lower alkoxycarbonyl group, lower alkylthio group, lower alkylsulfonyl group, halogen atom, phenylsulfonyl group substituted with cyano group, or phenyl group, Or a phenyl group substituted with 1 to 5 groups selected from the same or different lower alkyl groups, lower alkoxy groups, lower haloalkyl groups, lower haloalkoxy groups, lower alkylthio groups, lower alkylsulfonyl groups, halogen atoms, Or has one or more hetero atoms selected from the same or different oxygen atom, sulfur atom, and nitrogen atom, and is a halogen atom, a lower alkyl group, a lower alkoxy group, a lower haloalkyl group, a lower haloalkoxy. Group, nitro group One or more C 3 -C also be substituted by a substituent to 10 heterocyclic group,
Or: (Wherein, R ₅ , R ₆ , R ₇ , and R ₈ may be the same or different and each represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, a lower alkoxy lower alkyl group, a carboxy group, a lower alkoxycarbonyl group, Or a lower alkoxycarbonyl lower alkyl group, m represents an integer from 0 to 8, R ₉ represents an unsubstituted phenyl group, or 1 to
5 lower alkyl groups, lower alkoxy groups, lower haloalkyl groups, lower haloalkoxy groups, carboxy groups, lower alkoxycarbonyl groups, lower alkylthio groups, lower alkylsulfonyl groups, halogen atoms, phenyl groups substituted with cyano groups, or Having one or more hetero atoms selected from the same or different oxygen atoms, sulfur atoms, and nitrogen atoms, a halogen atom, a lower alkyl group, a lower alkoxy group, a lower haloalkyl group, a lower haloalkoxy group, X represents an oxygen atom or a lower alkoxycarbonyl group, a cyano group, or a nitro group, which may be substituted with one or more substituents selected from one or more substituents. In the case of a sulfur atom, R ₃ may represent a metal ion or a protonated organic base. Agricultural and horticultural disease control agents, comprising an isoxazolecarboxylic acid derivative represented by the formula:

In the above formula (I), the lower alkyl group in the definition of R _{1 to} R ₉ preferably has 1 to 6 carbon atoms, more preferably 1 to 4 carbon atoms, and these are linear. Or a branched shape.

Examples of such lower alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, t-butyl, n-pentyl, and isoamyl groups. , N-hexyl group and the like.

In the above formula (I), the lower alkyl group in the definition of R _{1 to} R ₉ is, specifically, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec- -Butoxy group, t-butoxy group, isoamyloxy group, n-hexyloxy group and the like.

In the above formula (I), the lower haloalkyl group in the definition of R _{1 to} R ₉ includes, specifically, trifluoromethyl group, difluoromethyl group, trichloromethyl group, dichloromethyl group, fluoromethyl group, Chloromethyl group, iodomethyl group, bromomethyl group, difluorochloromethyl group, 2,2,2-trifluoroethyl group, 2,2,2-
Examples thereof include a trichloroethyl group, a pentafluoroethyl group, and a pentachloroethyl group.

As the lower haloalkoxy group, specifically, a trifluoromethoxy group, a difluoromethoxy group,
Fluoromethoxy group, trichloromethoxy group, tribromomethoxy group, 2,2,2, -trifluoroethoxy group, 2,2,
Examples thereof include a 2, -trichloroethoxy group, a pentafluoroethoxy group, a 2-fluoroethoxy group, a 2-chloroethoxy group, a 2-bromoethoxy group, a 2-iodoethoxy group, and a 3-chloropropoxy group.

In the above general formula (I), the lower alkoxycarbonyl group in the definition of R _{1 to} R ₉ includes, for example, methoxycarbonyl group, ethoxycarbonyl group, n-propoxycarbonyl group, isopropoxycarbonyl group, t-butoxy group Examples thereof include a carbonyl group, a sec-butoxycarbonyl group, and an isoamyloxycarbonyl group.

In the above general formula (I), the lower alkenyl group in the definition of R ₄ includes, for example, vinyl group, 1-propenyl group, 2-propenyl group, 1-methyl-2-propenyl group, 2-methyl-2 -Propenyl group, 2-ethyl-2-propenyl group, 2-butenyl group, 1-methylbutenyl group, 2-
Methyl-2-butenyl group, 1-ethyl-2-butenyl group, 3
-Butenyl group, 2-pentenyl group, 3-pentenyl group, 4
-Pentenyl group, 2-hexenyl group, 2-hexenyl group,
C2-C2 groups such as 3-hexenyl group and 4-hexenyl group
Indicate six linear or branched alkynyl groups.

In the above formula (I), the lower alkynyl group in the definition of R ₄ includes, for example, 2-propynyl group, 1-
Methyl-2-propynyl group, 2-butynyl group, 1-ethyl-2-butynyl group, 3-butynyl group, 2-methyl-3-butynyl group, 2-pentynyl group, 4-pentynyl group, 2-hexynyl group, It represents a linear or branched alkynyl group having 3 to 6 carbon atoms, such as a 3-hexynyl group, a 4-hexynyl group, and a 5-hexynyl group.

In the above general formula (I), the lower alkylthio group in the definition of R ₃ and R ₄ includes a methylthio group, an ethylthio group, an n-propylthio group, a 1-methylethylthio group,
n-butylthio group, 1-methylpropylthio group, 2-methylpropylthio group, 1,1, -dimethylethylthio group, n-
Pentylthio group, n-hexylthio group, 1-methylbutylthio group, 2-methylbutylthio group, 3-methylbutylthio group, 1-ethylpropylthio group, 2-ethylpropylthio group, 1,1, -dimethylpropyl Examples include a thio group and a 2,2-dimethylpropylthio group.

In the above general formula (I), the lower alkylsulfonyl group in the definition of R ₃ and R ₄ includes, for example, methylsulfonyl group, ethylsulfonyl group, n-propylsulfonyl group, 1-methylethylsulfonyl group, n- Butylsulfonyl group, 1-methylpropylsulfonyl group, 1,1, -dimethylethylsulfonyl group, n-pentylsulfonyl group,
Examples thereof include a 1-methylbutylsulfonyl group, a 1-ethylpropylsulfonyl group, a 1-methylpentylsulfonyl group, a 1-ethylbutylsulfonyl group, and an n-hexylsulfonyl group.

In the above general formula (I), aralkyl groups in the definition of R ₄ include benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylpropyl, 2
-Phenylpropyl group, 3-phenylpropyl group, 1-methyl-1-phenylethyl group, 1-methyl-2-phenylethyl group, 1-phenylbutyl group, 2-phenylbutyl group, 3-phenylbutyl group, 4 -Phenylbutyl group, 1-
Methyl-1-phenylpropyl group, 1-methyl-2-phenylpropyl group, 1-methyl-3-phenylpropyl group, 5-
Examples thereof include a phenylpentyl group and a 6-phenylhexyl group.

In the general formula (I), the halogen atom in the definition of R _{1 to} R ₉ represents a chlorine atom, a bromine atom, an iodine atom or a fluorine atom.

In the above general formula (I), examples of the heterocycle having 3 to 10 carbon atoms in the definition of R ₃ and R ₉ include furan, thiophene, pyrrole, oxazole, isoxazole, thiazole, isothiazole, pyrazole and the like. Imidazole, 1,2,3-triazole, 1,3,4-triazole,
1,2,3-thiadiazole, 1,2,4-thiadiazole, 1,
2,5-thiadiazole, 1,3,4-thiadiazole, 1,3,4
-Oxadiazole, pyridine, pyrazine, pyridazine, pyrimidine, 1,2,4-triazine, 1,3,5-triazine, pyrrolidine, piperidine, morpholine, dithiolane, dithiane, piperazine, dioxolane, imidazolidine, quinoline, isoquinoline, Quinazoline, quinoxaline, cinnoline, phthalazine, indole, indazole, benzofuran, benzothiophene, benzimidazole, benzopyran, benzothian, benzodioxole, benzothiazole, benzoisothiazole, benzoxazole, benzoisoxazole, 1,2,3-benzo Examples thereof include thiadiazole and 1,2,3-benzotriazole.

In the above general formula (I), the metal ion is 1
Represents a valent or divalent metal ion, and includes an alkali metal ion such as a sodium ion and a potassium ion, and an alkaline earth metal ion such as a calcium ion and a copper ion.

The protonated organic base is C ₁
~C up to ₂₀ linear or branched and is lower alkoxy group, an alkyl group which may be substituted with such lower alkylthio group, it is substituted with such an unsubstituted or substituted benzyl group or unsubstituted or substituted phenyl group Also 4
Represents a quaternary ammonium ion or a pyridinium ion, such as an ammonium ion, a trimethylammonium ion, a triethylammonium ion, a benzyldimethylammonium ion, or a pyridinium ion;

The first plant disease controlling agent according to the present invention is in the form of a composition containing a derivative of the general formula (I) as an active ingredient and a solid or liquid conventional carrier mixed with the active ingredient. be able to. The isoxazolecarboxylic acid derivative of the general formula (I) is, as a preferred embodiment thereof,
Derivatives of the following general formulas (Ia), (Ib), (Ic), (Id), (Ie), (If) or (Ig) are included.

(A) Formula (Ia) (Wherein, R ₁ represents a halogen atom, a lower haloalkyl group or a lower haloalkoxy group, R ₂ represents a hydrogen atom,
An isoxazolecarboxylic acid derivative represented by a halogen atom or a lower alkyl group) or a salt thereof (formula (I)
The compound of a) is a known compound or a compound similar to the known compound).

(B) General formula (Ib) [In the formula, R ₁ represents a halogen atom, a lower haloalkyl group or a lower haloalkoxy group, R ₂ represents a hydrogen atom,
A halogen atom or a lower alkyl group; R _3a represents a lower alkyl group, a lower alkenyl group, a lower alkynyl group,
Alternatively, one or more lower alkyl groups, a cycloalkyl group having 3 to 8 carbon atoms which may be substituted with a carboxy group or a lower alkoxycarbonyl group, or a lower haloalkyl group, a lower haloalkenyl group, a lower haloalkynyl group, Lower alkoxy lower alkyl group, lower alkoxycarbonyl lower alkyl group, or phenyl group or the same or different lower alkyl group, lower alkoxy group, lower haloalkyl group, lower haloalkoxy group, lower alkylthio group, lower alkylsulfonyl group, halogen atom A phenyl group substituted with 1 to 5 groups selected from the group consisting of a halogen atom having one or more hetero atoms selected from the same or different oxygen atom, sulfur atom, and nitrogen atom; Atom, lower alkyl group, lower alcohol A heterocyclic group having 3 to 10 carbon atoms which may be substituted by one or more substituents selected from a xy group, a lower haloalkyl group, a lower haloalkoxy group, and a nitro group; (Wherein, R ₅ , R ₆ , R ₇ , and R ₈ may be the same or different and each represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, a lower alkoxy lower alkyl group, a carboxy group, a lower alkoxycarbonyl group, Or a lower alkoxycarbonyl lower alkyl group, m represents an integer from 0 to 8, R ₉ represents an unsubstituted phenyl group, or 1 to
5 lower alkyl groups, lower alkoxy groups, lower haloalkyl groups, lower haloalkoxy groups, carboxy groups, lower alkoxycarbonyl groups, lower alkylthio groups, lower alkylsulfonyl groups, halogen atoms, phenyl groups substituted with cyano groups, or Having one or more hetero atoms selected from the same or different oxygen atom, sulfur atom, nitrogen atom, halogen atom, lower alkyl group, lower alkoxy group, lower haloalkyl group, lower haloalkoxy group, A heterocyclic ring having 3 to 10 carbon atoms which may be substituted by one or more substituents selected from a lower alkoxycarbonyl group, a cyano group and a nitro group). Oxazole carboxylic acid ester derivatives (compounds of formula (Ib) are known compounds or Which is a compound).

(C) General formula (Ic) [In the formula, R ₁ represents a halogen atom, a lower haloalkyl group or a lower haloalkoxy group, R ₂ represents a hydrogen atom,
A halogen atom or a lower alkyl group; R _3a represents a lower alkyl group, a lower alkenyl group, a lower alkynyl group,
Alternatively, one or more lower alkyl groups, a cycloalkyl group having 3 to 8 carbon atoms which may be substituted with a carboxy group or a lower alkoxycarbonyl group, or a lower haloalkyl group, a lower haloalkenyl group, a lower haloalkynyl group, Lower alkoxy lower alkyl group, lower alkoxycarbonyl lower alkyl group, or phenyl group or the same or different lower alkyl group, lower alkoxy group, lower haloalkyl group, lower haloalkoxy group, lower alkylthio group, lower alkylsulfonyl group, halogen atom A phenyl group substituted with 1 to 5 groups selected from, or one or more hetero atoms selected from the same or different oxygen atom, sulfur atom, nitrogen atom, and halogen Atom, lower alkyl group, lower alcohol A heterocyclic group having 3 to 10 carbon atoms which may be substituted by one or more substituents selected from a xy group, a lower haloalkyl group, a lower haloalkoxy group, and a nitro group; (Wherein, R ₅ , R ₆ , R ₇ , and R ₈ may be the same or different and each represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, a lower alkoxy lower alkyl group, a carboxy group, a lower alkoxycarbonyl group, Or a lower alkoxycarbonyl lower alkyl group, m represents an integer from 0 to 8, R ₉ represents an unsubstituted phenyl group, or 1 to
5 lower alkyl groups, lower alkoxy groups, lower haloalkyl groups, lower haloalkoxy groups, carboxy groups, lower alkoxycarbonyl groups, lower alkylthio groups, lower alkylsulfonyl groups, halogen atoms, phenyl groups substituted with cyano groups, or Having one or more hetero atoms selected from the same or different oxygen atom, sulfur atom, nitrogen atom, halogen atom, lower alkyl group, lower alkoxy group, lower haloalkyl group, lower haloalkoxy group, A heterocyclic ring having 3 to 10 carbon atoms which may be substituted by one or more substituents selected from a lower alkoxycarbonyl group, a cyano group and a nitro group). Oxazole thiocarboxylic acid ester derivatives (compounds of formula (Ic) are known compounds or known compounds It is similar compounds).

(D) General formula (Id) (Wherein, R _1a represents a halogen atom or a lower haloalkoxy group, and R _3b and R _4a may be the same or different, and each represents a hydrogen atom, a lower alkyl group, a lower haloalkyl group, a lower alkoxy lower alkyl group. Or a phenyl lower alkyl group (the phenyl group is unsubstituted or may be substituted with 1 to 5 halogen atoms, lower alkyl groups, lower haloalkyl groups, or lower haloalkoxy groups). Isoxazolecarboxylic acid amide derivative (the compound of formula (Id) is a known compound or a compound similar to the known compound).

(E) General formula (Ie) [Wherein, R _1a represents a halogen atom or a lower haloalkoxy group, and R _3c may be substituted with a lower alkenyl group, a lower alkynyl group, or one or more carboxy groups or lower alkoxycarbonyl groups. A cycloalkyl group having 3 to 8 carbon atoms, or a lower haloalkenyl group, a lower haloalkynyl group, a lower alkoxycarbonyl group, a carboxy lower alkyl group, a lower alkoxycarbonyl lower alkyl group, a lower alkylcarbonyl group, a lower haloalkylcarbonyl group, lower Alkylsulfonyl group, lower haloalkylsulfonyl group, or unsubstituted benzoyl group, or 1 to 5 lower alkyl groups, lower alkoxy group, lower haloalkoxy group, lower haloalkyl group, lower alkoxycarbonyl group, lower alkylthio group, lower A benzoyl group substituted with a rualkylsulfonyl group, a halogen atom, a cyano group, or an unsubstituted phenylsulfonyl group, or 1 to 5 lower alkyl groups, lower alkoxy groups, lower haloalkyl groups, lower haloalkoxy groups, lower alkoxycarbonyl Group, lower alkylthio group, lower alkylsulfonyl group, halogen atom, phenylsulfonyl group substituted by cyano group,
Or a phenyl group, or the same or different lower alkyl groups, lower alkoxy groups, lower haloalkyl groups,
1 to 5 selected from a lower haloalkoxy group, a lower alkylthio group, a lower alkylsulfonyl group, and a halogen atom
Having one or more hetero atoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom, which may be the same or different, a halogen atom, a lower alkyl group, A heterocyclic group having 3 to 10 carbon atoms, which may be substituted by one or more substituents selected from an alkoxy group, a lower haloalkyl group, a lower haloalkoxy group, and a nitro group; (Wherein, R _5a represents a carboxy group or a lower alkoxycarbonyl group, and R _6a , R _7a , and R _8a may be the same or different, and each represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, a lower alkoxy lower group. An alkyl group, a carboxy group, a lower alkoxycarbonyl group or a lower alkoxycarbonyl lower alkyl group, m represents an integer from 0 to 8, R _9a is an unsubstituted phenyl group, or 1 to 5 lower alkyl groups; Lower alkoxy group, lower haloalkyl group, lower haloalkoxy group, carboxy group,
One or more selected from a lower alkoxycarbonyl group, a lower alkylthio group, a lower alkylsulfonyl group, a halogen atom, a phenyl group substituted with a cyano group, or an oxygen atom, a sulfur atom, and a nitrogen atom which may be the same or different. Having a hetero atom, a halogen atom, a lower alkyl group, a lower alkoxy group, a lower haloalkyl group,
Lower haloalkoxy group, lower alkoxycarbonyl group,
A heterocyclic ring having 3 to 10 carbon atoms which may be substituted by one or more substituents selected from a cyano group and a nitro group), and R ₄ represents a hydrogen atom, lower alkyl or A lower alkyl group, a lower alkynyl group, or a cycloalkyl group having 3 to 8 carbon atoms, which may be substituted with one or more lower alkyl groups, a carboxy group or a lower alkoxycarbonyl group, or a lower haloalkyl group; Lower haloalkenyl group, lower haloalkynyl group, lower alkoxy lower alkyl group, lower alkoxycarbonyl group, carboxy lower alkyl group, lower alkoxycarbonyl lower alkyl group, lower alkylcarbonyl group, lower haloalkylcarbonyl group, lower alkylsulfonyl group, lower haloalkyl Sulfonyl group or unsubstituted ben A zoyl group, or 1 to 5 lower alkyl groups, a lower alkoxy group, a lower haloalkoxy group, a lower haloalkyl group, a lower alkoxycarbonyl group, a lower alkylthio group, a lower alkylsulfonyl group,
A benzoyl group substituted with a halogen atom, a cyano group, or an unsubstituted phenylsulfonyl group, or 1 to 5
Lower alkyl group, lower alkoxy group, lower haloalkyl group, lower haloalkoxy group, lower alkoxycarbonyl group, lower alkylthio group, lower alkylsulfonyl group, halogen atom, phenylsulfonyl group substituted with cyano group, or phenyl group, Or a phenyl group substituted with 1 to 5 groups selected from the same or different lower alkyl groups, lower alkoxy groups, lower haloalkyl groups, lower haloalkoxy groups, lower alkylthio groups, lower alkylsulfonyl groups, halogen atoms, Alternatively, it has one or more hetero atoms selected from the same or different oxygen atom, sulfur atom, nitrogen atom, and is a halogen atom, a lower alkyl group, a lower alkoxy group, a lower haloalkyl group, a lower haloalkoxy. Group or nitro group A heterocyclic group having 3 to 10 carbon atoms which may be substituted by one or more substituents, or (Wherein, R ₅ , R ₆ , R ₇ , and R ₈ may be the same or different and each represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, a lower alkoxy lower alkyl group, a carboxy group, a lower alkoxycarbonyl group, Or a lower alkoxycarbonyl lower alkyl group, m represents an integer from 0 to 8, R ₉ represents an unsubstituted phenyl group, or 1 to
5 lower alkyl groups, lower alkoxy groups, lower haloalkyl groups, lower haloalkoxy groups, carboxy groups, lower alkoxycarbonyl groups, lower alkylthio groups, lower alkylsulfonyl groups, halogen atoms, phenyl groups substituted with cyano groups, or Having one or more heteroatoms selected from the same or different oxygen atom, sulfur atom, nitrogen atom, halogen atom, lower alkyl group, lower alkoxy group, lower haloalkyl group, lower haloalkoxy group, Represents a heterocyclic ring having 3 to 10 carbon atoms which may be substituted by one or more substituents selected from a lower alkoxycarbonyl group, a cyano group and a nitro group). Oxazolecarboxylic amide derivatives (the compound of formula (Ie) is a novel compound).

(F) General formula (If) [Wherein, R _1b represents a halogen atom, R _2a represents a lower alkyl group or a halogen atom, and R ₃ and R ₄ may be the same or different, and each represents a hydrogen atom, a lower alkyl group, a lower alkyl group. An alkenyl group, a lower alkynyl group, or a cycloalkyl group having 3 to 8 carbon atoms which may be substituted with one or more lower alkyl groups, carboxy groups or lower alkoxycarbonyl groups, or lower haloalkyl groups, lower haloalkenyls Group, lower haloalkynyl group, lower alkoxy lower alkyl group, lower alkoxycarbonyl group, carboxy lower alkyl group, lower alkoxycarbonyl lower alkyl group, lower alkylcarbonyl group, lower haloalkylcarbonyl group, lower alkylsulfonyl group, lower haloalkylsulfonyl group, Or unsubstituted Ben Benzoyl substituted with an yl group or 1 to 5 lower alkyl groups, lower alkoxy groups, lower haloalkoxy groups, lower haloalkyl groups, lower alkoxycarbonyl groups, lower alkylthio groups, lower alkylsulfonyl groups, halogen atoms, cyano groups Group, or unsubstituted phenylsulfonyl group, or 1 to 5 lower alkyl groups, lower alkoxy groups, lower haloalkyl groups,
Lower haloalkoxy group, lower alkoxycarbonyl group,
A lower alkylthio group, a lower alkylsulfonyl group, a phenylsulfonyl group substituted with a halogen atom or a cyano group, or a phenyl group or the same or different lower alkyl group, lower alkoxy group, lower haloalkyl group, lower haloalkoxy group, lower alkylthio group; Selected from a group represented by the formula:
A phenyl group substituted with up to 5 groups, or one or more hetero atoms selected from the same or different oxygen atom, sulfur atom, and nitrogen atom, a halogen atom, a lower alkyl group A heterocyclic group having 3 to 10 carbon atoms which may be substituted by one or more substituents selected from a lower alkoxy group, a lower haloalkyl group, a lower haloalkoxy group, and a nitro group; (Wherein, R ₅ , R ₆ , R ₇ , and R ₈ may be the same or different and each represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, a lower alkoxy lower alkyl group, a carboxy group, a lower alkoxycarbonyl group, Or a lower alkoxycarbonyl lower alkyl group, m represents an integer from 0 to 8, R ₉ represents an unsubstituted phenyl group, or 1 to
5 lower alkyl groups, lower alkoxy groups, lower haloalkyl groups, lower haloalkoxy groups, carboxy groups, lower alkoxycarbonyl groups, lower alkylthio groups, lower alkylsulfonyl groups, halogen atoms, phenyl groups substituted with cyano groups, or Having one or more hetero atoms selected from the same or different oxygen atom, sulfur atom, nitrogen atom, halogen atom, lower alkyl group, lower alkoxy group, lower haloalkyl group, lower haloalkoxy group, A heterocyclic ring having 3 to 10 carbon atoms which may be substituted by one or more substituents selected from a lower alkoxycarbonyl group, a cyano group and a nitro group). Oxazolecarboxylic amide derivatives (the compound of formula (If) is a novel compound).

(G) General formula (Ig) [Wherein, R _1c represents a lower haloalkyl group, R ₂ represents a hydrogen atom, a lower alkyl group or a halogen atom;
₃ and R ₄ may be the same or different, and
A hydrogen atom, a lower alkyl group, a lower alkenyl group, a lower alkynyl group, or a cycloalkyl group having 3 to 8 carbon atoms which may be substituted with one or more lower alkyl groups, carboxy groups or lower alkoxycarbonyl groups; Or a lower haloalkyl group, a lower haloalkenyl group, a lower haloalkynyl group, a lower alkoxy lower alkyl group, a lower alkoxycarbonyl group, a carboxy lower alkyl group, a lower alkoxycarbonyl lower alkyl group,
Lower alkylcarbonyl group, lower haloalkylcarbonyl group, lower alkylsulfonyl group, lower haloalkylsulfonyl group, or unsubstituted benzoyl group, or 1 to 5 lower alkyl groups, lower alkoxy groups, lower haloalkoxy groups, lower haloalkyl groups, Lower alkoxycarbonyl group, lower alkylthio group, lower alkylsulfonyl group, halogen atom, benzoyl group substituted by cyano group, or unsubstituted phenylsulfonyl group, or 1 to 5 lower alkyl groups, lower alkoxy groups, lower haloalkyl Groups, lower haloalkoxy groups, lower alkoxycarbonyl groups, lower alkylthio groups, lower alkylsulfonyl groups, halogen atoms, phenylsulfonyl groups substituted with cyano groups, or phenyl groups, or the same or different Grade alkyl group, a lower alkoxy group,
A lower haloalkyl group, a lower haloalkoxy group, a lower alkylthio group, a lower alkylsulfonyl group, a phenyl group substituted with 1 to 5 groups selected from halogen atoms,
Or has one or more hetero atoms selected from the same or different oxygen atom, sulfur atom, and nitrogen atom, and is a halogen atom, a lower alkyl group, a lower alkoxy group, a lower haloalkyl group, a lower haloalkoxy. A heterocyclic group having 3 to 10 carbon atoms, which may be substituted by one or more substituents selected from a nitro group, (Wherein, R ₅ , R ₆ , R ₇ , and R ₈ may be the same or different and each represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, a lower alkoxy lower alkyl group, a carboxy group, a lower alkoxycarbonyl group, Or a lower alkoxycarbonyl lower alkyl group, m represents an integer from 0 to 8, R ₉ represents an unsubstituted phenyl group, or 1 to
5 lower alkyl groups, lower alkoxy groups, lower haloalkyl groups, lower haloalkoxy groups, carboxy groups, lower alkoxycarbonyl groups, lower alkylthio groups, lower alkylsulfonyl groups, halogen atoms, phenyl groups substituted with cyano groups, or Having one or more hetero atoms selected from the same or different oxygen atom, sulfur atom, nitrogen atom, halogen atom, lower alkyl group, lower alkoxy group, lower haloalkyl group, lower haloalkoxy group, A heterocyclic ring having 3 to 10 carbon atoms which may be substituted by one or more substituents selected from a lower alkoxycarbonyl group, a cyano group and a nitro group). Oxazolecarboxylic amide derivatives (the compound of formula (Ig) is a novel compound).

In the second invention, a novel compound represented by the general formula (Ie) [Wherein, R _1a represents a halogen atom or a lower haloalkoxy group, and R _3c may be substituted with a lower alkenyl group, a lower alkynyl group, or one or more carboxy groups or lower alkoxycarbonyl groups. A cycloalkyl group having 3 to 8 carbon atoms, or a lower haloalkenyl group, a lower haloalkynyl group, a lower alkoxycarbonyl group, a carboxy lower alkyl group, a lower alkoxycarbonyl lower alkyl group, a lower alkylcarbonyl group, a lower haloalkylcarbonyl group, a lower Alkylsulfonyl group, lower haloalkylsulfonyl group, or unsubstituted benzoyl group, or 1 to 5 lower alkyl groups, lower alkoxy group, lower haloalkoxy group, lower haloalkyl group, lower alkoxycarbonyl group, lower alkylthio group, lower alkyl group; A benzoyl group substituted with a killsulfonyl group, a halogen atom, a cyano group, or an unsubstituted phenylsulfonyl group, or 1 to 5 lower alkyl groups, lower alkoxy groups, lower haloalkyl groups, lower haloalkoxy groups, lower alkoxycarbonyl Group, lower alkylthio group, lower alkylsulfonyl group, halogen atom, phenylsulfonyl group substituted by cyano group,
Or a phenyl group, or the same or different lower alkyl groups, lower alkoxy groups, lower haloalkyl groups,
1-5 selected from a lower haloalkoxy group, a lower alkylthio group, a lower alkylsulfonyl group, and a halogen atom
Having one or more heteroatoms selected from oxygen, sulfur and nitrogen, which may be the same or different, halogen atom, lower alkyl group, lower An alkoxy group, a lower haloalkyl group, a lower haloalkoxy group, a heterocyclic group having 3 to 10 carbon atoms which may be substituted by one or more substituents selected from a nitro group, or (Wherein, R _5a represents a carboxy group or a lower alkoxycarbonyl group, and R _6a , R _7a , and R _8a may be the same or different, and each represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, a lower alkoxy lower group. An alkyl group, a carboxy group, a lower alkoxycarbonyl group or a lower alkoxycarbonyl lower alkyl group, m represents an integer from 0 to 8, R _9a represents an unsubstituted phenyl group, or 1
-5 lower alkyl groups, lower alkoxy groups, lower haloalkyl groups, lower haloalkoxy groups, carboxy groups, lower alkoxycarbonyl groups, lower alkylthio groups, lower alkylsulfonyl groups, halogen atoms, phenyl groups substituted with cyano groups, Or having one or more hetero atoms selected from the same or different oxygen atom, sulfur atom, nitrogen atom, halogen atom, lower alkyl group, lower alkoxy group, lower haloalkyl group, lower haloalkoxy group , lower alkoxycarbonyl group, a group of cyano group, one or more heterocyclic rings having 3 to 10 carbon atoms, sometimes replaced by a substituent selected from nitro group), also R ₄ is , A hydrogen atom, a lower alkyl group, a lower alkenyl group, a lower alkynyl group, or one or more A lower alkyl group, a cycloalkyl group having 3 to 8 carbon atoms which may be substituted with a carboxy group or a lower alkoxycarbonyl group, or a lower haloalkyl group, a lower haloalkenyl group, a lower haloalkynyl group, a lower alkoxy lower alkyl group, a lower An alkoxycarbonyl group, a carboxy lower alkyl group, a lower alkoxycarbonyl lower alkyl group, a lower alkylcarbonyl group, a lower haloalkylcarbonyl group, a lower alkylsulfonyl group, a lower haloalkylsulfonyl group, or an unsubstituted benzoyl group, or 1 to 5 lower groups An alkyl group, a lower alkoxy group, a lower haloalkoxy group, a lower haloalkyl group, a lower alkoxycarbonyl group, a lower alkylthio group, a lower alkylsulfonyl group, a halogen atom, a benzoyl group substituted with a cyano group, Or unsubstituted phenylsulfonyl group, or 1 to 5 lower alkyl groups, lower alkoxy groups, lower haloalkyl groups, lower haloalkoxy groups, lower alkoxycarbonyl groups, lower alkylthio groups, lower alkylsulfonyl groups, halogen atoms, cyano, Selected from a phenylsulfonyl group substituted with a group, or a phenyl group, or the same or different lower alkyl group, lower alkoxy group, lower haloalkyl group, lower haloalkoxy group, lower alkylthio group, lower alkylsulfonyl group, and halogen atom A phenyl group substituted with 1 to 5 groups, or one or more heteroatoms selected from the same or different oxygen atom, sulfur atom, nitrogen atom, halogen atom, lower alkyl Group, lower alkoxy group, lower haloalkyl group, lower Haloalkoxy groups, one or more C 3 -C also be substituted by a substituent to 10 heterocyclic group selected from a nitro group, or the following formula (Wherein, R ₅ , R ₆ , R ₇ , and R ₈ may be the same or different and each represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, a lower alkoxy lower alkyl group, a carboxy group, a lower alkoxycarbonyl group, Or a lower alkoxycarbonyl lower alkyl group, m represents an integer from 0 to 8, R ₉ is an unsubstituted phenyl group, or 1 to 5 lower alkyl groups, lower alkoxy groups, lower haloalkyl groups, lower Selected from a haloalkoxy group, a carboxy group, a lower alkoxycarbonyl group, a lower alkylthio group, a lower alkylsulfonyl group, a halogen atom, a phenyl group substituted by a cyano group, or an oxygen atom, a sulfur atom, or a nitrogen atom which may be the same or different. Having one or more heteroatoms, a halogen atom, a lower alkyl group, a lower alkoxy group Group, a lower haloalkyl group, a lower haloalkoxy group, a lower alkoxycarbonyl group, a cyano group, a heterocyclic group having 3 to 10 carbon atoms which may be substituted by one or more substituents selected from nitro groups Isoxazolecarboxylic acid amide derivative represented by the formula:

In the third invention, the compound represented by the general formula (I
f) [Wherein, R _1b represents a halogen atom, R _2a represents a lower alkyl group or a halogen atom, and R ₃ and R ₄ may be the same or different, and each represents a hydrogen atom, a lower alkyl group, A lower alkenyl group, a lower alkynyl group, or a cycloalkyl group having 3 to 8 carbon atoms which may be substituted with one or more lower alkyl groups, a carboxy group or a lower alkoxycarbonyl group, or a lower haloalkyl group; Alkenyl group, lower haloalkynyl group, lower alkoxy lower alkyl group, lower alkoxycarbonyl group, carboxy lower alkyl group, lower alkoxycarbonyl lower alkyl group, lower alkylcarbonyl group, lower haloalkylcarbonyl group, lower alkylsulfonyl group, lower haloalkylsulfonyl group Or unsubstituted benzo Or a benzoyl substituted with 1 to 5 lower alkyl groups, lower alkoxy groups, lower haloalkoxy groups, lower haloalkyl groups, lower alkoxycarbonyl groups, lower alkylthio groups, lower alkylsulfonyl groups, halogen atoms, cyano groups. Group, or unsubstituted phenylsulfonyl group, or 1 to 5 lower alkyl groups, lower alkoxy groups, lower haloalkyl groups, lower haloalkoxy groups, lower alkoxycarbonyl groups, lower alkylthio groups, lower alkylsulfonyl groups, halogen atoms, A phenylsulfonyl group substituted with a cyano group,
Or a phenyl group, or the same or different lower alkyl groups, lower alkoxy groups, lower haloalkyl groups,
A lower haloalkoxy group, a lower alkylthio group, a lower alkylsulfonyl group, a phenyl group substituted with 1 to 5 groups selected from halogen atoms, or an oxygen atom, a sulfur atom, and a nitrogen atom which may be the same or different. Having one or more heteroatoms selected, a halogen atom, a lower alkyl group, a lower alkoxy group, a lower haloalkyl group, a lower haloalkoxy group, and one or more substituents selected from a nitro group; An optionally substituted heterocyclic group having 3 to 10 carbon atoms, or the following formula (Wherein, R ₅ , R ₆ , R ₇ , and R ₈ may be the same or different and each represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, a lower alkoxy lower alkyl group, a carboxy group, a lower alkoxycarbonyl group, Or a lower alkoxycarbonyl lower alkyl group, m represents an integer from 0 to 8, R ₉ is an unsubstituted phenyl group, or 1 to 5 lower alkyl groups, lower alkoxy groups, lower haloalkyl groups, lower Selected from a haloalkoxy group, a carboxy group, a lower alkoxycarbonyl group, a lower alkylthio group, a lower alkylsulfonyl group, a halogen atom, a phenyl group substituted with a cyano group, or an oxygen atom, a sulfur atom, or a nitrogen atom which may be the same or different. Having one or more heteroatoms, a halogen atom, a lower alkyl group, a lower alcohol A heterocyclic group having 3 to 10 carbon atoms which may be substituted by one or more substituents selected from a group, a lower haloalkyl group, a lower haloalkoxy group, a lower alkoxycarbonyl group, a cyano group and a nitro group. Isoxazolecarboxylic acid amide derivative represented by the formula:

Further, in the fourth invention, the general formula
(Ig) [Wherein, R _1c represents a lower haloalkyl group, R ₂ represents a hydrogen atom, a lower alkyl group or a halogen atom;
₃ and R ₄ may be the same or different, each having the same meaning as R ₃ and R ₄ in the above general formula (If)].

Next, the method for producing the compound of the general formula (I), which is the active ingredient in the first controlling agent of the present invention, will be described in detail.

(I) Isoxazole-5-carboxylic acid and its ester derivative can be produced by a method comprising the following reaction formula.

[0050] (Wherein Y represents a halogen atom, and R ₁ , R ₂ , and R ₃ represent the same meaning as described above).

That is, the oxime derivative represented by the general formula (II) and the acetylene carboxylic acid derivative represented by the general formula (III) are reacted in a suitable solvent in the presence of a deoxidizing agent to form a compound represented by the general formula ( The isoxazolecarboxylic acid ester derivative represented by I) can be produced. Here, examples of the deoxidizing agent include organic tertiary amines such as triethylamine, tributylamine, diethylisopropylamine, pyridine, 4-dimethylaminopyridine, 2,6-dimethylpyridine, N-methylaniline, and N-ethylaniline. And metal carbonates such as sodium bicarbonate, potassium bicarbonate, sodium carbonate and potassium carbonate, and alkali metal hydroxides such as potassium hydroxide, sodium hydroxide and barium hydroxide. Preferably,
The deoxidizing agent is triethylamine, potassium hydrogen carbonate, potassium carbonate or the like.

Examples of the solvent used in the reaction include water, aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride and 1,2, -dichloroethane; Ether, dibutyl ether, 1,2-dimethoxyethane,
1,2-diethoxyethane, tetrahydrofuran, ethers such as 1,4-dioxane, methyl acetate, ethyl acetate, esters such as butyl acetate, acetonitrile,
Nitriles such as propionitrile, ketones such as acetone and methyl ethyl ketone, pyridine and the like can be used, or a mixed solvent thereof can also be used. Preferably, 1,2-dimethoxyethane,
Ethyl acetate, dichloromethane and the like can be mentioned.

The reaction temperature is usually from -80 to 150 ° C, preferably from 0 to 100 ° C. The reaction time varies depending on the reaction temperature and the reaction substrate, but is usually completed in 30 minutes to 24 hours.

The compound of the general formula (I), which is the target compound, is collected from the reaction mixture by a usual post-treatment. For example,
It is obtained by adding water to the reaction mixture, washing with water, and distilling off the solvent. The obtained target compound can be purified by an operation such as column chromatography or recrystallization, if necessary.

(Ii) The ester compound of the general formula (I) can also be produced by a method comprising the following reaction formula.

[0056] (Wherein Y represents a halogen atom, and R ₁ , R ₂ , and R ₃ have the same meanings as described above).

That is, the compound represented by the general formula (IV) is hydrolyzed into a carboxylic acid derivative (V) and then halogenated to form an acid halide derivative represented by the general formula (VI). The compound represented by the general formula (I) can be produced by reacting with the compound represented by the formula (VII).

This hydrolysis reaction can be carried out in water or a mixed solvent of water and a suitable solvent in the presence of an acid or a base. Acids that can be used include hydrochloric acid, hydrobromic acid, p-
There are toluenesulfonic acid and the like, and usable bases include sodium hydroxide, potassium hydroxide, sodium carbonate, sodium hydrogen carbonate, potassium carbonate, potassium hydrogen carbonate and the like. As the halogenating agent, thionyl chloride, thionyl bromide, phosphoryl chloride,
Phosphoryl bromide, phosphorus pentachloride and the like can be used. Next, the resulting acid halide derivative of the general formula (VI) is reacted with a compound of the general formula (VII) in the presence of a suitable deoxidizing agent to obtain a compound of the general formula (VII)
The compound (I) can be produced.

Examples of the deoxidizing agent include triethylamine, tributylamine, diethylisopropylamine, pyridine, 4-dimethylaminopyridine, 2,6-dimethylpyridine, N, N-dimethylaniline and N, N-diethylaniline. Organic tertiary amines and metal carbonates such as sodium bicarbonate, potassium bicarbonate, sodium carbonate, potassium carbonate, potassium hydroxide, sodium hydroxide,
Alkali metal hydroxides such as barium hydroxide can be mentioned, and preferred are triethylamine, pyridine, potassium carbonate, sodium carbonate, sodium hydroxide, potassium hydroxide and the like.

Examples of the solvent used in the reaction include aromatic hydrocarbons such as benzene, toluene and xylene; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride and 1,2, -dichloroethane; diethyl ether; Dibutyl ether, 1,2-dimethoxyethane, 1,2-
Ethers such as diethoxyethane, tetrahydrofuran, 1,4-dioxane, esters such as methyl acetate, ethyl acetate, and butyl acetate; nitriles such as acetonitrile and propionitrile; ketones such as acetone and methyl ethyl ketone And amides such as dimethylformamide and dimethylacetamide; dimethylsulfoxide and pyridine; and a mixed solvent thereof. Preferably, chloroform, benzene, toluene, tetrahydrofuran and the like are mentioned. The reaction temperature is usually from -80 to 150 ° C, preferably from 0 to 100 ° C. The reaction time varies depending on the reaction temperature and the reaction substrate, but usually from 10 minutes
Complete in 24 hours.

The compound of the formula (I), which is the target compound, is collected from the reaction mixture by a usual post-treatment. For example,
It is obtained by adding water to the reaction mixture, washing with water, and distilling off the solvent. The obtained target product can be purified, if necessary, by an operation such as column chromatography or recrystallization.

(Iii) Further, when the compound of the general formula (I) is a derivative in the form of a carboxylic acid amide, it can also be produced by a method comprising the following reaction formula. (Where Y represents a halogen atom, Z represents a halogen atom, a lower alkylsulfonyl group or a lower alkylsulfonyloxy group, and R ₁ , R ₂ , R ₃ , and R ₄ have the same meanings as described above).

That is, when the compound of the general formula (I) is a carboxylic acid amide derivative represented by the general formula (IX), first, the primary amine derivative represented by the general formula (X) is converted to a compound represented by the general formula (VI) Is reacted with an acid halide derivative represented by the above formula to obtain a compound represented by the general formula (VIII). afterwards,
The compound of formula (VIII) may be isolated or isolated without isolation.
With the compound represented by Thus, the general formula (VI
A carboxylic acid amide derivative represented by the formula (II) is represented by the general formula (XI)
By reacting the compound represented by the formula with an appropriate base, an amide type compound of the general formula (IX) can be obtained.

Examples of the base usable here include organic tertiary amines such as pyridine, 4-dimethylaminopyridine, 2,6-dimethylpyridine, N, N-dimethylaniline, and N, N-diethylaniline. Metal carbonates such as sodium bicarbonate, potassium bicarbonate, sodium carbonate and potassium carbonate; alkali metal hydroxides such as potassium hydroxide, sodium hydroxide and barium hydroxide; metals such as sodium hydride and potassium hydride Examples include hydrides, organolithium compounds such as n-butyllithium and lithium diisopropylamide, and metal alkoxide compounds such as sodium methoxide, sodium ethoxide and potassium t-butoxide. Preferably,
The base is potassium carbonate, sodium carbonate, sodium hydroxide, potassium hydroxide, sodium hydride and the like.

Solvents used in the reaction include aromatic hydrocarbons such as benzene, toluene and xylene, halogenated hydrocarbons such as monochlorobenzene, diethyl ether, dibutyl ether, 1,2-dimethoxyethane, 1,2-dimethoxyethane, and the like. 2-diethoxyethane, tetrahydrofuran, 1,4
-Ethers such as dioxane, nitriles such as acetonitrile and propionitrile, amides such as dimethylformamide and dimethylacetamide, dimethylsulfoxide and pyridine, and a mixed solvent thereof may also be used. But preferably, tetrahydrofuran, dimethylformamide,
Dimethyl sulfoxide and the like.

The reaction temperature is usually from -80 to 150 ° C, preferably from 0 to 100 ° C. The reaction time varies depending on the reaction temperature and the reaction substrate, but is usually completed in 10 minutes to 24 hours.

The compound of the general formula (I) as the reaction target is collected from the reaction mixture by a usual post-treatment. For example,
It is obtained by adding water to the reaction mixture, washing with water, and distilling off the solvent. The obtained target product can be purified, if necessary, by an operation such as column chromatography or recrystallization.

The isoxazole-5-carboxylic acid derivative represented by the general formula (IV) and the isoxazole-5-carbonyl halide derivative represented by the general formula (V) are prepared by the method of Acta. Chem. Scand. Ser. B, B38 , 815 (1984), Bioche
m. Pharmacol. 18 , 569 (1969), Farmaco, Ed.Sci. 41 , 440 (1
986), Liebigs Ann.Chem. 8 , 815 (1993), JP-A-62-50.
No. 1416, J. Heterocycl.Chem. 24 , 43 (1987), Ann.
369, 300 (1909), Ist.Lombard Sci.Pt.I.Classe Sci.Ma
te Nat 94A, 729 (1960) , Gazz.Chim.Ital. 91, 47 (196
1), JP-A-2-292284, J. Med.Chem. 39 , 2232 (199
6), Synthesis, 69 (1986), J. Org. Chem. 26 , 1514 (196
1), Journal of Industrial Science, 66 , 1831 (1963), Journal of Industrial Science, 66 , 18
38 (1963), Ber. 106 , 3345 (1973), J. Am. Pharm. Assoc.
42 , 594 (1953), Gazz. Chim. Ital., 81 , 117 (1951) and the like, or a method analogous thereto.

In the production of the compound of the general formula (V), the compound of the general formula (XII) may be oxidized with an oxidizing agent to produce the compound of the general formula (V) as shown in the following formula. it can.

[0070] (Wherein R ₁ and R ₂ represent the same meaning as described above, and R ₁₁ represents a hydroxymethyl group or an aldehyde group).

That is, in the above reaction, the general formula
The carboxylic acid derivative of the general formula (V) can be synthesized by oxidizing the compound of the formula (XII) using a suitable oxidizing agent in a solvent. Examples of the oxidizing agent include inorganic peroxides such as potassium permanganate, potassium dichromate, and sodium perchlorate, and peroxides such as aqueous hydrogen peroxide, m-chloroperbenzoic acid, peracetic acid, and t-butyl hydroperoxide. Can be used. Alternatively, oxygen oxidation can be carried out using a metal such as platinum, cobalt, ruthenium and a complex thereof as a catalyst. These reactions are usually performed in a solvent. Examples of the solvent that can be used include ketones such as acetone and methyl ethyl ketone, organic acids such as acetic acid and propionic acid, organic halogenated hydrocarbons such as dichloromethane, chloroform and chlorobenzene, and water, or a mixed solvent thereof. Preferably, water, acetic acid, acetone, chloroform and the like are used.

The compound of the above general formula (XII) is obtained from Farmaco, E
d.Sci. 41, 440 (1986) , JP-62-501416, JP-A No.
59-137472, Bull.Chem. Soc. Jp. 57 , 2184, (1984)
And the like, and can be easily produced according to them.

(Iv) In the compound of the general formula (I), when R ₁ is a haloalkoxy group,
It can be produced by a method comprising the following reaction formula. That is, it can be produced by reacting a compound of the general formula (XIII) with water to obtain a compound of the general formula (XIV), and further reacting the compound with a compound of the general formula (XV).

[0074] (Wherein, R ₂ , R ₃ , R ₄ , X, Y and Z have the same meaning as described above, and R ₁₂ represents a lower haloalkyl group).

In the above reaction, the step of producing the general formula (XIV) from the general formula (XIII) can be carried out in water or a mixed solvent of water and a suitable solvent in the presence of a base. Examples of the base include inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, and potassium hydrogen carbonate. As the solvent, water alone or ethers such as tetrahydrofuran, 1,4-dioxane and 1,2-dimethoxyethane, nitriles such as acetonitrile and propionitrile, ketones such as acetone and methyl ethyl ketone, dimethylformamide, dimethylacetamide Amides such as
Dimethyl sulfoxide, and a mixed solvent of these with water.

The reaction of the general formulas (XIV) and (XV) is carried out in a solvent in the presence of a suitable base.

Examples of usable bases include metal carbonates such as sodium carbonate and potassium carbonate, alkali metal hydroxides such as potassium hydroxide, sodium hydroxide and barium hydroxide, sodium hydride, potassium hydride and the like. Examples thereof include metal hydrides, organic lithium compounds such as n-butyllithium and lithium diisopropylamide, and metal alkoxide compounds such as potassium t-butoxide. Of these, preferred are potassium carbonate, sodium carbonate, and sodium hydride.

Solvents used in the reaction include aromatic hydrocarbons such as benzene, toluene and xylene, halogenated hydrocarbons such as monochlorobenzene, diethyl ether, dibutyl ether, 1,2-dimethoxyethane, 1,2-dimethoxyethane and the like. 2-diethoxyethane, tetrahydrofuran, 1,4
Ethers such as dioxane, amides such as dimethylformamide and dimethylacetamide, dimethylsulfoxide and pyridine can be used, and a mixed solvent thereof can also be used. , Dimethyl sulfoxide and the like.

The reaction temperature is usually from -80 to 150 ° C., preferably from 0 to 100 ° C. The reaction time varies depending on the reaction temperature and the reaction substrate, but is usually completed in 10 minutes to 24 hours.

The compound of the general formula (I) as the reaction target is collected from the reaction mixture by a usual post-treatment. For example,
It is obtained by adding water to the reaction mixture, washing with water, and distilling off the solvent. The obtained target product can be purified, if necessary, by an operation such as column chromatography or recrystallization.

Next, the production examples of some examples of the derivatives of the general formula (I) used in the first controlling agent of the present invention will be specifically described in the following examples.

Example 1 Preparation of 3-chloro-N- (1-methoxycarbonyl-2-phenyl) ethyl-isoxazole-5-carboxylic acid amide (Compound No. 697 shown in Table 1 below) L-phenylalanine 1.0g of methyl ester hydrochloride (4.8mm
ol), 1.1 g (10.6 mmol) of triethylamine and 20 ml of chloroform were added to 0.8 g (4.8 mmol) of 3-chloroisoxazole-5-carboxylic acid chloride under ice-cooling and stirring.
Was added dropwise. After the addition, the mixture was stirred at room temperature for 2 hours to complete the reaction. The reaction solution was washed with 1 N hydrochloric acid, a 5% sodium hydrogen carbonate solution and then with a saturated saline solution, dried over anhydrous sodium sulfate, and then the solvent was distilled off from the reaction solution under reduced pressure. The residue was purified by silica gel column chromatography to give the title compound.
1.4 g (90% yield) were obtained.

Example 2 Preparation of 3-trifluoromethylisoxazole-5-carboxylic acid (compound No. 101 shown in Table 1 below) 4.5 g (27 mmol) of 3-trifluoromethylisoxazole-5-methanol Then, 5.5 g (35 mmol) of potassium permanganate was dissolved in 160 ml of water and added dropwise to a mixed solution of 100 ml of a 0.5 N aqueous solution of sodium hydroxide and 100 ml of a 0.5 N aqueous sodium hydroxide solution with stirring under ice-cooling. 1
While keeping the temperature at 3 ° C. or lower, the whole amount was dropped in 20 minutes. After stirring for 2 hours under ice cooling, the reaction solution was acidified with sulfuric acid and extracted with ether. The obtained extract was washed with 1N hydrochloric acid, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to give the title compound (4.3 g)
(88% yield). The melting point was 127-129 ° C.

Example 3 Preparation of 3-chloroisoxazole-5-carboxylic acid methylthioester (compound No. 202 shown in Table 1) 5.6 g (12 mmol) of a 15% sodium methyl mercaptan solution
1.7 g (10 mmol) of 3-chloroisoxazole-5-carboxylic acid chloride was added dropwise to a mixed solution of 20 ml of tetrahydrofuran and ice-cooled solution with stirring. After the addition, the mixture was stirred at room temperature for 3 hours to complete the reaction. The reaction solution was washed with water and dried over anhydrous sodium sulfate, and then the solvent was distilled off from the reaction solution under reduced pressure to obtain 1.2 g (yield: 62%) of the title compound. Recrystallization from n-hexane showed a melting point of 61-62 ° C.

Example 4 Preparation of 3-chloroisoxazol-5-ylmethyl 3-chloroisoxazole-5-carboxylate (compound No. 39 shown in Table 1) 1 g of 3-chloroisoxazole-5-methanol (7.5 g) mo
l), a mixed solution of 3-chloroisoxazole-5-carbonyl chloride and 10 ml of toluene was added dropwise to a mixed solution of 0.9 g (9 mmol) of triethylamine and 10 ml of toluene while stirring at 20 ° C. After the dropwise addition, the mixture was heated under reflux for 1 hour to complete the reaction. The reaction solution was washed with 1 N hydrochloric acid, 3% sodium hydrogen carbonate solution and saturated saline, and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the obtained residue was purified by silica gel column chromatography to obtain 0.8 g (yield: 40%) of pale yellow crystals. 77-81 ° C
showed that.

Hereinafter, typical examples of the isoxazolecarboxylic acid derivative represented by the general formula (I) are shown in the following Table.
Although exemplified in 1, the present invention is not limited to only these exemplified compounds. Incidentally, among the compounds of the general formula (I), examples of the compound in the form of a carboxylic acid or an ester thereof are shown in Tables 1- (1) to 1- (16) under the title of the general formula (I ′). Is shown. Examples of compounds in the form of carboxylic acid amides are shown in Tables 1- (17) to 1- (73) under the title of general formula (IX).

[0087]

Next, a method for formulating a plant disease controlling agent for agricultural and horticultural use, that is, a fungicide for agricultural and horticultural use according to the present invention will be described. When the active ingredient compound represented by the above general formula (I) is used as a fungicide for agricultural and horticultural use, it may be used alone. It is preferably used after being formulated into a pharmaceutical preparation. That is, a compound of the general formula (I) is mixed with a suitable carrier,
Further, a surfactant and other formulation auxiliaries can be added as required to form a formulation generally used as a formulation of a pesticide composition. For example, powders, fine granules, granules, tablets, wettable powders, concentrated emulsions, suspoemulsions, wettable granules, flowables, liquids, emulsions,
Oils, pastes, aerosols, microcapsules,
It can be formulated into a coating agent for seeds. The dosage forms that can be formulated are not limited to those listed here.
In addition, one or more compounds of the general formula (I) according to the present invention can be compounded as an active ingredient, that is, an active ingredient.

As the liquid carrier used in the above-mentioned preparation, generally, aromatic hydrocarbons (eg, benzene, toluene, xylene, alkylnaphthalene, etc.), aliphatic hydrocarbons (eg, cyclohexane, paraffins, etc.), alcohols (Eg, ethylene glycol, isopropyl alcohol, butanol, etc.), ethers (eg, dioxane, tetrahydrofuran, etc.), esters (eg, glycerin esters of fatty acids, etc.), ketones (eg, acetone, methyl ethyl ketone, etc.), amides (Eg, dimethylformamide, dimethylacetamide, etc.), sulfoxides (eg, dimethylsulfoxide, etc.), water and the like can be used. As solid carriers, kaolin, bentonite, clay, talc, attapull guide, montmorillonite, diatomaceous earth, silica sand, synthetic silicate, alumina, white carbon, calcium carbonate, calcium phosphate, starch, wood sawdust, soybean powder, walnut shell powder, tobacco Stem powder, ammonium sulfate, urea, vermiculite and the like can be mentioned.

Examples of the surfactant include anionic surfactants such as alkyl sulfates, alkyl (aryl) sulfonates, dialkyl sulfosuccinates and polyoxyethylene alkyl aryl ether phosphates, and polyoxyethylene alkyl ethers. And nonionic surfactants such as polyoxyethylene alkylaryl ether, sorbitan fatty acid ester and polyoxyethylene sorbitan acid ester. Examples of the formulation auxiliary include a physical property improver, a decomposition inhibitor, a binder and the like. The amount of the compound of the formula (I) to be added to the preparation can be appropriately varied depending on the dosage form of the preparation and the method of use, and it is generally desirable to use it in the range of 0.1 to 95% by weight.

The agricultural and horticultural plant disease controlling agent of the first invention includes, in addition to the compound of the present invention, which is an active ingredient in the above-mentioned various preparation forms, if desired, other known active compounds.
For example, fungicides, insecticides, acaricides, nematicides, insect growth regulators, herbicides, bird repellents, growth regulators, fertilizers, soil conditioners, and the like may be added.

The method for applying the agricultural and horticultural disease controlling agent of the present invention is not particularly limited, and may be any of foliage application, water surface application (paddy rice), nursery box application (paddy rice), soil application, seed treatment and the like. Can also be applied. The application rate of the compound used as the active ingredient in actual application can be appropriately changed according to the type of the compound, the target of application (eg, target disease, target crop, etc.), the timing of application, and the like.

For example, in the case of foliar application, a liquid preparation such as a wettable powder, a flowable, and a granule wettable powder is added to a solution having a concentration of 5 to 1000 ppm, preferably 10 to 500 ppm as an active ingredient in water or the like. 30 to 1000 liters per 10 ares, usually applied according to the type and vegetation of the target crop, for example, 70 to 180 liters for paddy rice, 100 to 300 liters for field crops, 300 to 800 liters for fruit trees It can be used at the application rate. When a solid preparation such as a powder is sprayed on foliage, the preparation can be used at an application rate of 2 to 5 kg of the preparation per 10 ares (active ingredient amount: 5 to 150 g / 10 ares).
In the case of paddy rice surface application, a solid preparation such as a granule is applied in an amount of 0.3 to 5 kg of the preparation per 10 ares (as an active ingredient amount,
50-300 g / 10 ares).

[0094] In the case of application of the rice seedling box, the treatment time is from immediately after seeding to the seedling box until immediately before rice planting.
There is no particular limitation, and a solid preparation such as a granule is applied to a nursery box (size: length × width × height 60 cm × 30 cm × 3 cm) in an application amount of 20 to 100 g (active ingredient: 0.5 to 20 g / nurture box). It can be used, and the formulation such as wettable powder, flowable, granule wettable powder and the like can be diluted with water or the like as required, and applied at a rate of 0.03 to 1 liter per seedling box (active ingredient amount: 0.5 to 20 g / seedling Box).

[0095] For soil application, uniformly to the soil surface or soil, it is possible to use a solid formulation such as granules at an application rate of 1 m ² per 3~300g (1~100g / m ² as an active ingredient amount) , wettable powders, flowable, formulations to be used in a liquid such as water dispersible granules (as an active ingredient, 1 to 100 g / m ²⁾ application rate of from 0.1 to 10 per liter 1 m ² was diluted with water or the like be used in Can be. Furthermore, these solid preparations and preparations used in liquid form can be applied to local treatment on the soil surface of the base of the target crop or in the soil (active ingredient amount: 5 to 500 mg / strain).

In the case of treating seeds, liquid preparations such as wettable powders, flowables and wettable powders may be diluted with water or the like, if necessary, to give an application rate of 1 to 5% of the seed weight ( Spraying of 0.5 to 20 g of the active ingredient / seed weight of 1 kg) or blending treatment using a mortar mixer or the like can be used. The amount can be used in the treatment of a dressing or the like in an amount of 0.5 to 20 g / seed weight 1 kg).

[0097]

Hereinafter, examples of the preparation of the plant disease controlling agent of the present invention will be described more specifically with reference to Examples, but the scope of the present invention is not limited to the following Examples.

Example 5 (Powder) 2 parts of Compound No. 2 in Table 1, PAP (physical property improver) 0.3
Parts and 97.7 parts of clay are uniformly mixed and ground to give a dust containing 2% of active ingredient. Granules can be obtained in the same manner by using each of the compounds shown in Table 1 in place of Compound No. 2.

Example 6 (Wettable powder) 20 parts of compound No. 371 in Table 1, 3 parts of sodium alkylbenzenesulfonate, 5 parts of polyoxymethylene nonylphenyl ether, 5 parts of white carbon and clay
67 parts are uniformly mixed and pulverized to obtain a wettable powder containing 20% of active ingredient. In addition, a wettable powder can be obtained in the same manner by using each of the compounds shown in Table 1 in place of compound No. 371.

Example 7 (Emulsion) 30 parts of Compound No. 202 in Table 1 and methyl ethyl ketone 5
5 parts and polyoxyethylene nonyl phenyl ether 1
When 5 parts are mixed and dissolved, an emulsion containing 30% of the active ingredient is obtained. Emulsions can be obtained in the same manner by using each of the compounds shown in Table 1 in place of Compound No. 202.

Example 8 (Sol) A mixture of 40 parts of the compound of the compound No. 703 in Table 1, 2 parts of lauryl sulfate, 2 parts of sodium alkylnaphthalenesulfonate, 1 part of methylcellulose and 55 parts of water was uniformly mixed to give an active ingredient. A sol containing 40% of the components is obtained. Compound No. 703
Alternatively, a sol can be obtained in the same manner using each of the compounds shown in Table 1.

Example 9 (Granules) A kneading machine was prepared by adding 10 parts of compound No. 717 in Table 1, 1 part of lauryl sulfate, 5 parts of calcium ligninsulfonate, 30 parts of bentonite and 54 parts of clay to 15 parts of water. Then, the mixture is granulated by a granulator and dried by a fluidized drier to obtain a granule containing 10% of the active ingredient. Granules can be obtained in the same manner by using each of the compounds shown in Table 1 instead of Compound No. 717.

[0103]

EFFECT OF THE INVENTION The compound of the general formula (I) used in the first invention is highly controlled against plant diseases such as rice blast, rice sheath blight, barley powdery mildew, cucumber downy mildew and the like. It has an effect and is useful as an active ingredient of an agricultural and horticultural fungicide.
The plant diseases to be controlled by the control agent of the present invention are not limited to those exemplified above.

Next, the general formula (I) used in the first present invention
Test Example 1 shows a specific test example on the usefulness of the compound of Example 1.
~ 3. Test Example 1 Rice blast control effect test The third leaf stage seedling (5 seedlings per pot) of paddy rice (cultivar: Asahi) cultivated in a greenhouse in a plastic pot with a diameter of 6 cm in Example 2 Prepared according to Table 1 above
Using an automatic spraying machine, 10 ml of a diluted wettable powder containing the compound shown in (1) as an active ingredient was sprayed per pot. Seven days after drug treatment, rice blast fungus ( Pyricularia oryz) previously formed on oatmeal agar medium
ae : Pyridylaria oryzae conidia are adjusted to a concentration of 5 × 10 ⁵ spores (ml) / ml with a 50 ppm aqueous solution of a spreading agent (polyoxyethylene alkyl ether), and this is used with a spray gun. Spray inoculated.

After being kept in an inoculation box at 24 ° C. and 100% humidity overnight, they were transferred to a greenhouse at 24 ° C. to promote the onset of the disease. Six days after the inoculation, the total number of rice blast spots per pot of the third leaf was investigated, and the control value (%) was calculated by the following formula. This test was performed in three repetitions per chemical concentration group, the average control value (%) was determined, and converted to an evaluation value according to the following criteria. In addition, phytotoxicity to rice was investigated according to the following criteria. Table 2 shows the results. In addition, the evaluation value of the control value and the investigation index of the chemical damage are the same in Test Examples 2 and 3 below.

[0106] Investigation index of phytotoxicity 5: Severe 4: Severe 3: Many 2: Slight 1: Slight 0: None

[0107] Comparative compound A: Compound described in JP-B-43-112 Comparative drug B: compound described in JP-A-1-230563 Comparative drug C: compound described in PCT International Publication WO96 / 16954

Test Example 2 Rice blast water surface application effect test No. 5 of paddy rice (cultivar: Asahi) cultivated in a greenhouse in a Wagner pot having a size of 1/10000 ares under flooded conditions (water depth: 3 cm)
Granules prepared in accordance with Example 5 were sprayed on leaf seedlings (5 seedlings per strain per pot) at 3 kg per 10 ares. 7 of chemical treatment
Days later, the rice blast fungus ( Pyricularia oryzae) previously formed on the oatmeal agar medium
The conidia of Oryzae) were adjusted to a spore concentration of 5 × 10 ⁵ spores (number) / ml with a 50 ppm aqueous solution of a spreading agent (polyoxyethylene alkyl ether), and spray-inoculated with a spray gun.

After overnight in an inoculation box at 24 ° C and 100% humidity,
It was transferred to a greenhouse at 4 ° C to promote disease. 6 days after inoculation of the 5th leaf
The total number of rice blast spots per pot was investigated, and Test Example 1
The control value (%) was calculated in the same manner as described above. This test was performed in a three-repeat system for each drug, and the evaluation value of the control effect and the degree of phytotoxicity to rice were displayed in the same manner as in Test Example 1. Table 3 shows the results.

[0110]

Test Example 3 Rice blast nursery box treatment effect test Nursery box for test in a greenhouse (length × width × height: 15 cm × 12 cm × 3c)
m) on the 2.5th leaf stage seedling of rice (variety: Asahi)
5 g of the granules prepared according to Example 5 were sprayed per box.
One day after the chemical treatment, the seedlings were transplanted into a Wagner pot having a size of 1/10000 ares, one plant and five seedlings per one pot were planted in five pots and cultivated under flooded conditions (water depth: 3 cm). 30 days after transplantation, conidia of Pyricularia oryzae ( Pyricularia oryzae ) previously formed on an oatmeal agar medium were spore-concentrated at a concentration of 5 × 10 ^{5 with} a 50 ppm aqueous solution of a spreading agent (polyoxyethylene alkyl ether). The number of spores was adjusted to (number) / ml, and spray inoculation was performed using a spray gun.

After being kept in an inoculation box at 24 ° C. and 100% humidity overnight, they were transferred to a greenhouse at 24 ° C. to promote the onset of the disease. 6 days after inoculation 1
The total number of rice blast lesions per pot was investigated, and the average total number of lesions per pot in five pots was determined.
The control value (%) was calculated in the same manner as described above. This test was performed in a three-repeat system for each drug, and the evaluation value of the control effect and the degree of phytotoxicity to rice were displayed in the same manner as in Test Example 1. Table 4 shows the results.

[0113]

 ────────────────────────────────────────────────── ─── Continuing on the front page (72) Inventor Tatsuya Masumizu 3-11-25-207 Higashi-Hachiman II, Hiratsuka-shi, Kanagawa Prefecture (72) Inventor Masato Ando 1-6-16-503 Okada, Atsugi-shi, Kanagawa Prefecture No. (72) Inventor Hideki Ohno 501-1 Toda, Atsugi-shi, Kanagawa Prefecture No. 203 Crest Onuki 203 (72) Inventor Seiichi Kutsuma 1-5-901-901 Tsumada Higashi, Atsugi-shi, Kanagawa Prefecture (72) Inventor Nobuya Maehara Kanagawa 2385 Toda, Atsugi-shi, Tohoku Hokuko Chemical Dormitory (72) Inventor Yoshihisa Watanabe 2352 Toda, Atsugi-shi, Kanagawa 1F term (reference) 4C056 AA01 AB01 AC01 AD01 AE03 FA03 FB03 FB17 FC01 4H011 AA01 BB10 DA02 DA15 DD03 DD04

Claims (9)

[Claims] 1. The compound of the general formula (I) [Wherein, R ₁ represents a halogen atom, a lower haloalkyl group or a lower haloalkoxy group, R ₂ represents a hydrogen atom, a halogen atom or a lower alkyl group, and X represents an oxygen atom, a sulfur atom or an NR ₄ group. And R ₃ and R ₄ may be the same or different, and each independently represents a hydrogen atom, a lower alkyl group, a lower alkenyl group, a lower alkynyl group, or one or more lower alkyl groups, a carboxy group or a lower group. A cycloalkyl group having 3 to 8 carbon atoms which may be substituted with an alkoxycarbonyl group, or a lower haloalkyl group, a lower haloalkenyl group, a lower haloalkynyl group, a lower alkoxy lower alkyl group, a lower alkoxycarbonyl group, a carboxy lower alkyl group , Lower alkoxycarbonyl, lower alkyl group, lower alkylcarbonyl group, lower halo Alkylcarbonyl group, lower alkylsulfonyl group, lower haloalkylsulfonyl group, or unsubstituted benzoyl group or 1 to 5 lower alkyl groups, lower alkoxy group, lower haloalkoxy group, lower haloalkyl group, lower alkoxycarbonyl group, lower alkylthio group Group, lower alkylsulfonyl group, halogen atom, benzoyl group substituted with cyano group, or unsubstituted phenylsulfonyl group, or 1 to 5 lower alkyl groups, lower alkoxy groups, lower haloalkyl groups,
Lower haloalkoxy group, lower alkoxycarbonyl group,
A lower alkylthio group, a lower alkylsulfonyl group, a phenylsulfonyl group substituted with a halogen atom or a cyano group, or a phenyl group or the same or different lower alkyl group, lower alkoxy group, lower haloalkyl group, lower haloalkoxy group, lower alkylthio group; Selected from a group represented by the formula:
A phenyl group substituted with up to 5 groups, or one or more hetero atoms selected from the same or different oxygen atom, sulfur atom, and nitrogen atom, a halogen atom, a lower alkyl group A heterocyclic group having 3 to 10 carbon atoms which may be substituted by one or more substituents selected from a lower alkoxy group, a lower haloalkyl group, a lower haloalkoxy group, and a nitro group; (Wherein, R ₅ , R ₆ , R ₇ , and R ₈ may be the same or different and each represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, a lower alkoxy lower alkyl group, a carboxy group, a lower alkoxycarbonyl group, Or a lower alkoxycarbonyl lower alkyl group, m represents an integer from 0 to 8, R ₉ represents an unsubstituted phenyl group, or 1 to
5 lower alkyl groups, lower alkoxy groups, lower haloalkyl groups, lower haloalkoxy groups, carboxy groups, lower alkoxycarbonyl groups, lower alkylthio groups, lower alkylsulfonyl groups, halogen atoms, phenyl groups substituted with cyano groups, or Having one or more heteroatoms selected from the same or different oxygen atom, sulfur atom, nitrogen atom, halogen atom, lower alkyl group, lower alkoxy group, lower haloalkyl group, lower haloalkoxy group, X represents an oxygen atom or a heterocyclic ring having 3 to 10 carbon atoms which may be substituted by one or more substituents selected from a lower alkoxycarbonyl group, a cyano group and a nitro group. In the case of a sulfur atom, R ₃ may represent a metal ion or a protonated organic base. And a plant disease control agent for agricultural and horticultural use, comprising an isoxazole carboxylic acid derivative represented by the following formula: 2. Formula (Ia) (Wherein, R ₁ represents a halogen atom, a lower haloalkyl group or a lower haloalkoxy group, R ₂ represents a hydrogen atom,
The plant disease controlling agent for agricultural and horticultural use according to claim 1, comprising an isoxazolecarboxylic acid derivative represented by a halogen atom or a lower alkyl group) or a salt thereof as an active ingredient. 3. A compound of the general formula (Ib) [In the formula, R ₁ represents a halogen atom, a lower haloalkyl group or a lower haloalkoxy group, R ₂ represents a hydrogen atom,
A halogen atom or a lower alkyl group; R _3a represents a lower alkyl group, a lower alkenyl group, a lower alkynyl group,
Alternatively, one or more lower alkyl groups, a cycloalkyl group having 3 to 8 carbon atoms which may be substituted with a carboxy group or a lower alkoxycarbonyl group, or a lower haloalkyl group, a lower haloalkenyl group, a lower haloalkynyl group, Lower alkoxy lower alkyl group, lower alkoxycarbonyl lower alkyl group, or phenyl group or the same or different lower alkyl group, lower alkoxy group, lower haloalkyl group, lower haloalkoxy group, lower alkylthio group, lower alkylsulfonyl group, halogen atom Having a phenyl group substituted with 1 to 5 groups selected from the group consisting of, or one or more hetero atoms selected from the same or different oxygen atom, sulfur atom, and nitrogen atom; Atom, lower alkyl group, lower alkyl Alkoxy groups, lower haloalkyl groups, lower haloalkoxy groups, carbon atoms, which may also be substituted by one or more substituents selected from a nitro group
3 to 10 heterocyclic groups, or the following formula (Wherein, R ₅ , R ₆ , R ₇ , and R ₈ may be the same or different and each represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, a lower alkoxy lower alkyl group, a carboxy group, a lower alkoxycarbonyl group, Or a lower alkoxycarbonyl lower alkyl group, m represents an integer from 0 to 8, R ₉ represents an unsubstituted phenyl group, or 1 to
5 lower alkyl groups, lower alkoxy groups, lower haloalkyl groups, lower haloalkoxy groups, carboxy groups, lower alkoxycarbonyl groups, lower alkylthio groups, lower alkylsulfonyl groups, halogen atoms, phenyl groups substituted with cyano groups, or Having one or more hetero atoms selected from the same or different oxygen atom, sulfur atom, nitrogen atom, halogen atom, lower alkyl group, lower alkoxy group, lower haloalkyl group, lower haloalkoxy group, A heterocyclic ring having 3 to 10 carbon atoms which may be substituted by one or more substituents selected from a lower alkoxycarbonyl group, a cyano group and a nitro group). Oxazole carboxylic acid ester derivative, or general formula (Ic) [In the formula, R ₁ represents a halogen atom, a lower haloalkyl group or a lower haloalkoxy group, R ₂ represents a hydrogen atom,
A halogen atom or a lower alkyl group; R _3a represents a lower alkyl group, a lower alkenyl group, a lower alkynyl group,
Alternatively, one or more lower alkyl groups, a cycloalkyl group having 3 to 8 carbon atoms which may be substituted with a carboxy group or a lower alkoxycarbonyl group, or a lower haloalkyl group, a lower haloalkenyl group, a lower haloalkynyl group, Lower alkoxy lower alkyl group, lower alkoxycarbonyl lower alkyl group, or phenyl group or the same or different lower alkyl group, lower alkoxy group, lower haloalkyl group, lower haloalkoxy group, lower alkylthio group, lower alkylsulfonyl group, halogen atom Having a phenyl group substituted with 1 to 5 groups selected from the group consisting of, or one or more hetero atoms selected from the same or different oxygen atom, sulfur atom, and nitrogen atom; Atom, lower alkyl group, lower alkyl Alkoxy groups, lower haloalkyl groups, lower haloalkoxy groups, one or more C 3 -C also be substituted by a substituent to 10 heterocyclic group selected from a nitro group, or the following formula (Wherein, R ₅ , R ₆ , R ₇ , and R ₈ may be the same or different and each represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, a lower alkoxy lower alkyl group, a carboxy group, a lower alkoxycarbonyl group, Or a lower alkoxycarbonyl lower alkyl group, m represents an integer from 0 to 8, R ₉ represents an unsubstituted phenyl group, or 1 to
5 lower alkyl groups, lower alkoxy groups, lower haloalkyl groups, lower haloalkoxy groups, carboxy groups, lower alkoxycarbonyl groups, lower alkylthio groups, lower alkylsulfonyl groups, halogen atoms, phenyl groups substituted with cyano groups, or Having one or more hetero atoms selected from the same or different oxygen atom, sulfur atom, nitrogen atom, halogen atom, lower alkyl group, lower alkoxy group, lower haloalkyl group, lower haloalkoxy group, A heterocyclic ring having 3 to 10 carbon atoms which may be substituted by one or more substituents selected from a lower alkoxycarbonyl group, a cyano group and a nitro group). The agricultural product according to claim 1, which comprises an oxazole thiocarboxylic acid ester derivative as an active ingredient. Disease control agent for the arts. 4. The general formula (Id) (In the formula, R _1a represents a halogen atom or a lower haloalkoxy group, and R _3b and R _4a may be the same or different and each represents a hydrogen atom, a lower alkyl group, a lower haloalkyl group, a lower alkoxy lower alkyl group. Or a phenyl lower alkyl group, wherein the phenyl group is unsubstituted or has 1 to 5 halogen atoms, a lower alkyl group,
A lower haloalkyl group or a lower haloalkoxy group), which is an isoxazolecarboxylic acid amide derivative represented by the formula (1) as an active ingredient. 5. Formula (Ie) [Wherein, R _1a represents a halogen atom or a lower haloalkoxy group, and R _3c may be substituted with a lower alkenyl group, a lower alkynyl group, or one or more carboxy groups or lower alkoxycarbonyl groups. A cycloalkyl group having 3 to 8 carbon atoms, or a lower haloalkenyl group, a lower haloalkynyl group, a lower alkoxycarbonyl group, a carboxy lower alkyl group, a lower alkoxycarbonyl lower alkyl group, a lower alkylcarbonyl group, a lower haloalkylcarbonyl group, lower Alkylsulfonyl group, lower haloalkylsulfonyl group, or unsubstituted benzoyl group, or 1 to 5 lower alkyl groups, lower alkoxy group, lower haloalkoxy group, lower haloalkyl group, lower alkoxycarbonyl group, lower alkylthio group, lower Benzoyl group substituted by alkylsulfonyl group, halogen atom, cyano group, or unsubstituted phenylsulfonyl group, or 1 to 5 lower alkyl groups, lower alkoxy groups, lower haloalkyl groups, lower haloalkoxy groups, lower alkoxycarbonyl Group, lower alkylthio group, lower alkylsulfonyl group, halogen atom, phenylsulfonyl group substituted by cyano group,
Or a phenyl group, or the same or different lower alkyl groups, lower alkoxy groups, lower haloalkyl groups,
1 to 5 selected from a lower haloalkoxy group, a lower alkylthio group, a lower alkylsulfonyl group, and a halogen atom
Having one or more hetero atoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom, which may be the same or different, a halogen atom, a lower alkyl group, A heterocyclic group having 3 to 10 carbon atoms, which may be substituted by one or more substituents selected from an alkoxy group, a lower haloalkyl group, a lower haloalkoxy group, and a nitro group; (Wherein, R _5a represents a carboxy group or a lower alkoxycarbonyl group, and R _6a , R _7a , and R _8a may be the same or different, and each represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, a lower alkoxy lower group. An alkyl group, a carboxy group, a lower alkoxycarbonyl group or a lower alkoxycarbonyl lower alkyl group, m represents an integer from 0 to 8, R _9a is an unsubstituted phenyl group, or 1 to 5 lower alkyl groups; Lower alkoxy group, lower haloalkyl group, lower haloalkoxy group, carboxy group,
One or more selected from a lower alkoxycarbonyl group, a lower alkylthio group, a lower alkylsulfonyl group, a halogen atom, a phenyl group substituted with a cyano group, or an oxygen atom, a sulfur atom, and a nitrogen atom which may be the same or different. Having a hetero atom, a halogen atom, a lower alkyl group, a lower alkoxy group, a lower haloalkyl group,
Lower haloalkoxy group, lower alkoxycarbonyl group,
A heterocyclic ring having 3 to 10 carbon atoms which may be substituted by one or more substituents selected from a cyano group and a nitro group), and R ₄ represents a hydrogen atom, lower alkyl or A lower alkyl group, a lower alkynyl group, or a cycloalkyl group having 3 to 8 carbon atoms, which may be substituted with one or more lower alkyl groups, a carboxy group or a lower alkoxycarbonyl group, or a lower haloalkyl group; Lower haloalkenyl group, lower haloalkynyl group, lower alkoxy lower alkyl group, lower alkoxycarbonyl group, carboxy lower alkyl group, lower alkoxycarbonyl lower alkyl group, lower alkylcarbonyl group, lower haloalkylcarbonyl group, lower alkylsulfonyl group, lower haloalkyl Sulfonyl group or unsubstituted ben A zoyl group, or 1 to 5 lower alkyl groups, a lower alkoxy group, a lower haloalkoxy group, a lower haloalkyl group, a lower alkoxycarbonyl group, a lower alkylthio group, a lower alkylsulfonyl group,
A benzoyl group substituted with a halogen atom, a cyano group, or an unsubstituted phenylsulfonyl group, or 1 to 5
Lower alkyl group, lower alkoxy group, lower haloalkyl group, lower haloalkoxy group, lower alkoxycarbonyl group, lower alkylthio group, lower alkylsulfonyl group, halogen atom, phenylsulfonyl group substituted with cyano group, or phenyl group, Or a phenyl group substituted with 1 to 5 groups selected from the same or different lower alkyl groups, lower alkoxy groups, lower haloalkyl groups, lower haloalkoxy groups, lower alkylthio groups, lower alkylsulfonyl groups, halogen atoms, Alternatively, it has one or more hetero atoms selected from the same or different oxygen atom, sulfur atom, nitrogen atom, and is a halogen atom, a lower alkyl group, a lower alkoxy group, a lower haloalkyl group, a lower haloalkoxy. Group or nitro group A heterocyclic group having 3 to 10 carbon atoms which may be substituted by one or more substituents, or (Wherein, R ₅ , R ₆ , R ₇ , and R ₈ may be the same or different and each represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, a lower alkoxy lower alkyl group, a carboxy group, a lower alkoxycarbonyl group, Or a lower alkoxycarbonyl lower alkyl group, m represents an integer from 0 to 8, R ₉ represents an unsubstituted phenyl group, or 1 to
5 lower alkyl groups, lower alkoxy groups, lower haloalkyl groups, lower haloalkoxy groups, carboxy groups, lower alkoxycarbonyl groups, lower alkylthio groups, lower alkylsulfonyl groups, halogen atoms, phenyl groups substituted with cyano groups, or Having one or more hetero atoms selected from the same or different oxygen atom, sulfur atom, nitrogen atom, halogen atom, lower alkyl group, lower alkoxy group, lower haloalkyl group, lower haloalkoxy group, A heterocyclic ring having 3 to 10 carbon atoms which may be substituted by one or more substituents selected from a lower alkoxycarbonyl group, a cyano group and a nitro group). An oxazolecarboxylic acid amide derivative is contained as an active ingredient.
The plant disease controlling agent for agricultural and horticultural use according to 1. 6. General formula (If) [Wherein, R _1b represents a halogen atom, R _2a represents a lower alkyl group or a halogen atom, and R ₃ and R ₄ may be the same or different, and each represents a hydrogen atom, a lower alkyl group, a lower alkyl group. An alkenyl group, a lower alkynyl group, or a cycloalkyl group having 3 to 8 carbon atoms which may be substituted with one or more lower alkyl groups, carboxy groups or lower alkoxycarbonyl groups, or lower haloalkyl groups, lower haloalkenyls Group, lower haloalkynyl group, lower alkoxy lower alkyl group, lower alkoxycarbonyl group, carboxy lower alkyl group, lower alkoxycarbonyl lower alkyl group, lower alkylcarbonyl group, lower haloalkylcarbonyl group, lower alkylsulfonyl group, lower haloalkylsulfonyl group, Or unsubstituted Ben Benzoyl substituted with an yl group or 1 to 5 lower alkyl groups, lower alkoxy groups, lower haloalkoxy groups, lower haloalkyl groups, lower alkoxycarbonyl groups, lower alkylthio groups, lower alkylsulfonyl groups, halogen atoms, cyano groups Group, or unsubstituted phenylsulfonyl group, or 1 to 5 lower alkyl groups, lower alkoxy groups, lower haloalkyl groups,
Lower haloalkoxy group, lower alkoxycarbonyl group,
A lower alkylthio group, a lower alkylsulfonyl group, a phenylsulfonyl group substituted with a halogen atom or a cyano group, or a phenyl group or the same or different lower alkyl group, lower alkoxy group, lower haloalkyl group, lower haloalkoxy group, lower alkylthio group; Selected from a group represented by the formula:
A phenyl group substituted with up to 5 groups, or one or more hetero atoms selected from the same or different oxygen atom, sulfur atom, and nitrogen atom, a halogen atom, a lower alkyl group A lower alkoxy group, a lower haloalkyl group, a lower haloalkoxy group, a heterocyclic group having 3 to 10 carbon atoms which may be substituted with one or more substituents selected from nitro groups, or
Next formula (Wherein, R ₅ , R ₆ , R ₇ , and R ₈ may be the same or different and each represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, a lower alkoxy lower alkyl group, a carboxy group, a lower alkoxycarbonyl group, Or a lower alkoxycarbonyl lower alkyl group, m is an integer from 0 to 8, R ₉ is an unsubstituted phenyl group, or 1 to 5
Lower alkyl groups, lower alkoxy groups, lower haloalkyl groups, lower haloalkoxy groups, carboxy groups, lower alkoxycarbonyl groups, lower alkylthio groups, lower alkylsulfonyl groups, halogen atoms, phenyl groups substituted with cyano groups, or the same Or one or more heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom which may be different, a halogen atom, a lower alkyl group, a lower alkoxy group, a lower haloalkyl group, a lower haloalkoxy group, a lower Which represents a heterocyclic group having 3 to 10 carbon atoms which may be substituted by one or more substituents selected from an alkoxycarbonyl group, a cyano group and a nitro group). The plant for agricultural and horticultural use according to claim 1, which comprises a carboxylic acid amide derivative as an active ingredient. Disease control agent. 7. General formula (Ig) [Wherein, R _1c represents a lower haloalkyl group, R ₂ represents a hydrogen atom, a lower alkyl group or a halogen atom;
₃ and R ₄ may be the same or different, and
A hydrogen atom, a lower alkyl group, a lower alkenyl group, a lower alkynyl group, or a cycloalkyl group having 3 to 8 carbon atoms which may be substituted with one or more lower alkyl groups, carboxy groups or lower alkoxycarbonyl groups; Or a lower haloalkyl group, a lower haloalkenyl group, a lower haloalkynyl group, a lower alkoxy lower alkyl group, a lower alkoxycarbonyl group, a carboxy lower alkyl group, a lower alkoxycarbonyl lower alkyl group,
Lower alkylcarbonyl group, lower haloalkylcarbonyl group, lower alkylsulfonyl group, lower haloalkylsulfonyl group, or unsubstituted benzoyl group, or 1 to 5 lower alkyl groups, lower alkoxy groups, lower haloalkoxy groups, lower haloalkyl groups, Lower alkoxycarbonyl group, lower alkylthio group, lower alkylsulfonyl group, halogen atom, benzoyl group substituted by cyano group, or unsubstituted phenylsulfonyl group, or 1 to 5 lower alkyl groups, lower alkoxy groups, lower haloalkyl Groups, lower haloalkoxy groups, lower alkoxycarbonyl groups, lower alkylthio groups, lower alkylsulfonyl groups, halogen atoms, phenylsulfonyl groups substituted with cyano groups, or phenyl groups, or the same or different Grade alkyl group, a lower alkoxy group,
A lower haloalkyl group, a lower haloalkoxy group, a lower alkylthio group, a lower alkylsulfonyl group, a phenyl group substituted with 1 to 5 groups selected from halogen atoms,
Or one or more heteroatoms selected from the same or different oxygen atom, sulfur atom, nitrogen atom, halogen atom, lower alkyl group, lower alkoxy group, lower haloalkyl group, lower haloalkoxy A heterocyclic group having 3 to 10 carbon atoms which may be substituted by one or more substituents selected from a nitro group, (Wherein, R ₅ , R ₆ , R ₇ , and R ₈ may be the same or different and each represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, a lower alkoxy lower alkyl group, a carboxy group, a lower alkoxycarbonyl group, Or a lower alkoxycarbonyl lower alkyl group, m represents an integer from 0 to 8, R ₉ represents an unsubstituted phenyl group, or 1 to
5 lower alkyl groups, lower alkoxy groups, lower haloalkyl groups, lower haloalkoxy groups, carboxy groups, lower alkoxycarbonyl groups, lower alkylthio groups, lower alkylsulfonyl groups, halogen atoms, phenyl groups substituted with cyano groups, or Having one or more hetero atoms selected from the same or different oxygen atom, sulfur atom, nitrogen atom, halogen atom, lower alkyl group, lower alkoxy group, lower haloalkyl group, lower haloalkoxy group, Represents a heterocyclic ring having 3 to 10 carbon atoms which may be substituted by one or more substituents selected from a lower alkoxycarbonyl group, a cyano group and a nitro group). An oxazolecarboxylic acid amide derivative is contained as an active ingredient.
The plant disease controlling agent for agricultural and horticultural use according to 1. 8. The formula (Ie) [Wherein, R _1a represents a halogen atom or a lower haloalkoxy group, and R _3c may be substituted with a lower alkenyl group, a lower alkynyl group, or one or more carboxy groups or lower alkoxycarbonyl groups. A cycloalkyl group having 3 to 8 carbon atoms, or a lower haloalkenyl group, a lower haloalkynyl group, a lower alkoxycarbonyl group, a carboxy lower alkyl group, a lower alkoxycarbonyl lower alkyl group, a lower alkylcarbonyl group, a lower haloalkylcarbonyl group, lower Alkylsulfonyl group, lower haloalkylsulfonyl group, or unsubstituted benzoyl group, or 1 to 5 lower alkyl groups, lower alkoxy group, lower haloalkoxy group, lower haloalkyl group, lower alkoxycarbonyl group, lower alkylthio group, lower Benzoyl group substituted by alkylsulfonyl group, halogen atom, cyano group, or unsubstituted phenylsulfonyl group, or 1 to 5 lower alkyl groups, lower alkoxy groups, lower haloalkyl groups, lower haloalkoxy groups, lower alkoxycarbonyl Group, lower alkylthio group, lower alkylsulfonyl group, halogen atom, phenylsulfonyl group substituted by cyano group,
Or a phenyl group, or the same or different lower alkyl groups, lower alkoxy groups, lower haloalkyl groups,
1 to 5 selected from a lower haloalkoxy group, a lower alkylthio group, a lower alkylsulfonyl group, and a halogen atom
Having one or more hetero atoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom, which may be the same or different, a halogen atom, a lower alkyl group, A heterocyclic group having 3 to 10 carbon atoms, which may be substituted by one or more substituents selected from an alkoxy group, a lower haloalkyl group, a lower haloalkoxy group, and a nitro group; (Wherein, R _5a represents a carboxy group or a lower alkoxycarbonyl group, and R _6a , R _7a , and R _8a may be the same or different, and each represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, a lower alkoxy lower group. An alkyl group, a carboxy group, a lower alkoxycarbonyl group or a lower alkoxycarbonyl lower alkyl group, m represents an integer from 0 to 8, R _9a is an unsubstituted phenyl group, or 1 to 5 lower alkyl groups; Lower alkoxy group, lower haloalkyl group, lower haloalkoxy group, carboxy group,
One or more selected from a lower alkoxycarbonyl group, a lower alkylthio group, a lower alkylsulfonyl group, a halogen atom, a phenyl group substituted with a cyano group, or an oxygen atom, a sulfur atom, and a nitrogen atom which may be the same or different. Having a hetero atom, a halogen atom, a lower alkyl group, a lower alkoxy group, a lower haloalkyl group,
Lower haloalkoxy group, lower alkoxycarbonyl group,
A heterocyclic ring having 3 to 10 carbon atoms which may be substituted by one or more substituents selected from a cyano group and a nitro group), and R ₄ represents a hydrogen atom, lower alkyl or A lower alkyl group, a lower alkynyl group, or a cycloalkyl group having 3 to 8 carbon atoms, which may be substituted with one or more lower alkyl groups, a carboxy group or a lower alkoxycarbonyl group, or a lower haloalkyl group; Lower haloalkenyl group, lower haloalkynyl group, lower alkoxy lower alkyl group, lower alkoxycarbonyl group, carboxy lower alkyl group, lower alkoxycarbonyl lower alkyl group, lower alkylcarbonyl group, lower haloalkylcarbonyl group, lower alkylsulfonyl group, lower haloalkyl Sulfonyl group or unsubstituted ben A zoyl group, or 1 to 5 lower alkyl groups, a lower alkoxy group, a lower haloalkoxy group, a lower haloalkyl group, a lower alkoxycarbonyl group, a lower alkylthio group, a lower alkylsulfonyl group,
A benzoyl group substituted with a halogen atom, a cyano group, or an unsubstituted phenylsulfonyl group, or 1 to 5
Lower alkyl group, lower alkoxy group, lower haloalkyl group, lower haloalkoxy group, lower alkoxycarbonyl group, lower alkylthio group, lower alkylsulfonyl group, halogen atom, phenylsulfonyl group substituted with cyano group, or phenyl group, Or a phenyl group substituted with 1 to 5 groups selected from the same or different lower alkyl groups, lower alkoxy groups, lower haloalkyl groups, lower haloalkoxy groups, lower alkylthio groups, lower alkylsulfonyl groups, halogen atoms, Alternatively, it has one or more hetero atoms selected from the same or different oxygen atom, sulfur atom, nitrogen atom, and is a halogen atom, a lower alkyl group, a lower alkoxy group, a lower haloalkyl group, a lower haloalkoxy. Group or nitro group A heterocyclic group having 3 to 10 carbon atoms which may be substituted by one or more substituents, or (Wherein, R ₅ , R ₆ , R ₇ , and R ₈ may be the same or different and each represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, a lower alkoxy lower alkyl group, a carboxy group, a lower alkoxycarbonyl group, Or a lower alkoxycarbonyl lower alkyl group, m is an integer from 0 to 8, R ₉ is an unsubstituted phenyl group, or 1 to 5
Lower alkyl groups, lower alkoxy groups, lower haloalkyl groups, lower haloalkoxy groups, carboxy groups, lower alkoxycarbonyl groups, lower alkylthio groups, lower alkylsulfonyl groups, halogen atoms, phenyl groups substituted with cyano groups, or the same Or one or more heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom which may be different, a halogen atom, a lower alkyl group, a lower alkoxy group, a lower haloalkyl group, a lower haloalkoxy group, a lower Which represents a heterocyclic group having 3 to 10 carbon atoms which may be substituted by one or more substituents selected from an alkoxycarbonyl group, a cyano group and a nitro group). Carboxamide derivatives. 9. The formula (If) [Wherein, R _1b represents a halogen atom, R _2a represents a lower alkyl group or a halogen atom, and R ₃ and R ₄ may be the same or different, and each represents a hydrogen atom, a lower alkyl group, A lower alkenyl group, a lower alkynyl group, a cycloalkyl group having 3 to 8 carbon atoms which may be substituted with one or more lower alkyl groups, a carboxy group or a lower alkoxycarbonyl group, or a lower haloalkyl group; Alkenyl group, lower haloalkynyl group, lower alkoxy lower alkyl group, lower alkoxycarbonyl group, carboxy lower alkyl group, lower alkoxycarbonyl lower alkyl group, lower alkylcarbonyl group, lower haloalkylcarbonyl group, lower alkylsulfonyl group, lower haloalkylsulfonyl group Or unsubstituted Benzoyl group or 1-5 lower alkyl groups, lower alkoxy groups, lower haloalkoxy groups,
Lower haloalkyl group, lower alkoxycarbonyl group, lower alkylthio group, lower alkylsulfonyl group, halogen atom, benzoyl group substituted with cyano group, or unsubstituted phenylsulfonyl group, or 1 to 5 lower alkyl groups, lower alkoxy group Group, lower haloalkyl group, lower haloalkoxy group, lower alkoxycarbonyl group, lower alkylthio group, lower alkylsulfonyl group,
A halogen atom, a phenylsulfonyl group substituted with a cyano group, or a phenyl group, or the same or different lower alkyl group, lower alkoxy group, lower haloalkyl group, lower haloalkoxy group, lower alkylthio group,
A lower alkylsulfonyl group, a phenyl group substituted by 1 to 5 groups selected from halogen atoms, or one or more oxygen atoms, sulfur atoms, and nitrogen atoms which may be the same or different A carbon atom having a hetero atom, which may be substituted by one or more substituents selected from a halogen atom, a lower alkyl group, a lower alkoxy group, a lower haloalkyl group, a lower haloalkoxy group, and a nitro group; To 10 heterocyclic groups, or the following formula (Wherein, R ₅ , R ₆ , R ₇ , and R ₈ may be the same or different and each represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, a lower alkoxy lower alkyl group, a carboxy group, a lower alkoxycarbonyl group, Or a lower alkoxycarbonyl lower alkyl group, m represents an integer from 0 to 8, R ₉ represents an unsubstituted phenyl group, or 1 to
5 lower alkyl groups, lower alkoxy groups, lower haloalkyl groups, lower haloalkoxy groups, carboxy groups, lower alkoxycarbonyl groups, lower alkylthio groups, lower alkylsulfonyl groups, halogen atoms, phenyl groups substituted with cyano groups, or Having one or more hetero atoms selected from the same or different oxygen atom, sulfur atom, nitrogen atom, halogen atom, lower alkyl group, lower alkoxy group, lower haloalkyl group, lower haloalkoxy group, A heterocyclic ring having 3 to 10 carbon atoms which may be substituted by one or more substituents selected from a lower alkoxycarbonyl group, a cyano group and a nitro group). Oxazolecarboxamide derivatives.