JP2002193710A - Pyrimidine or triazine derivative and fungicide for agriculture and horticulture - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a new fungicide which has high control effects against plant diseases, especially wheat powdery mildew, without affecting crops. SOLUTION: A pyrimidine or triazine derivative represented by general formula [I] (A is nitrogen atom or CR3; R1 and R2 are each independently H, a halogen atom, a 1 to 6C alkyl, a 2 to 6C alkenyl, a 2 to 6C alkynyl, a 3 to 6C cycloalkyl, or the like; R3 is H, a 1 to 6C alkyl, a 1 to 6C alkoxy or a halogen; the group represented by the general formula II is a 5 to 6-membered nitrogen-containing heterogeneous ring or its benzo-condensed ring type nitrogen- containing heterogeneous ring which may contain or be replaced with sulfur atom, oxygen atom or nitrogen atom in addition to the shown nitrogen atom), an antifungal agent which contains the pyrimidine or triazine derivative and used for agriculture and horticulture, and an intermediate for producing the derivative are provided.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

TECHNICAL FIELD The present invention relates to a novel pyrimidine or triazine derivative and a fungicide for agricultural and horticultural use containing the derivative as an active ingredient.

[0002]

2. Description of the Related Art As a compound related to a pyrimidine derivative of the compound of the present invention, a 4-aminopyrimidine derivative described as a pharmaceutical in US Pat. No. 5,525,604 and EP-A-640599 is disclosed in International Publication W.
There is a pyrimidine derivative described as a herbicide in O94 / 17059, but none of them mentions an agricultural and horticultural fungicide. Also, French Patent No. 147652
No. 9 describes a benzimidazoyl sulfonamide derivative having insecticidal and fungicidal activities, but does not disclose the compound of the present invention. Compounds related to the triazine derivative of the compound of the present invention are described in JP-A-47-36837, JP-A-49-17677, and Industrial Chemical Journal, Vol. 73, No. 5, p. 1000 (1970). There are triazine derivatives described as coloring agents for textile products, but none of them describe an agricultural and horticultural fungicide.

[0003]

SUMMARY OF THE INVENTION The present invention provides a novel pyrimidine or triazine derivative and a fungicide for agricultural and horticultural use containing the same as an active ingredient.

[0004]

The present inventors have synthesized various novel pyrimidine and triazine derivatives to develop a drug having a bactericidal activity superior to conventionally known bactericides, and have studied their physiological activities. As a result of the investigation, it was found that the compound of the present invention exhibited a remarkable effect as an agricultural and horticultural fungicide, and the present invention was completed.

That is, the present invention relates to (1) a compound represented by the general formula [I]:

[0006]

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In the formula, A represents a nitrogen atom or CR ³ ;
R ¹ and R ² each independently represent a hydrogen atom, a halogen atom, a (C ₁ -C ₆ ) alkyl group, a (C ₂ -C ₆ ) alkenyl group, a (C ₂
-C ₆ ) alkynyl group, (C ₃ -C ₆ ) cycloalkyl group, (C _1-
(C ₄ ) haloalkyl group, (C ₁ -C ₆ ) alkoxy group, (C ₂ -C ₆ )
Alkenyloxy group, (C ₂ -C ₆ ) alkynyloxy group, (C
₃ -C ₆₎ cycloalkoxy group, (C ₁ -C ₄₎ haloalkoxy group, cyano (C ₁ -C ₄₎ alkyloxy group, (C ₁ -C ₄₎ alkoxy (C ₁ -C ₄₎ alkyl group , (C ₃ -C ₆₎ cycloalkyl (C ₁ -C ₄₎ alkyloxy group, a benzyloxy group [said group halogen atom, (C ₁ -C ₄₎ alkyl or (C ₁ -C ₄₎ alkoxy group May be substituted. ], (C ₁ -C ₆ ) alkylthio group, phenoxy group [the group is a halogen atom, (C ₁ -C 6
₄ ) It may be substituted with an alkyl group or a (C ₁ -C ₄ ) alkoxy group. ], A phenyl group, a di (C ₁ -C ₄₎ alkylamino group, a cyano group or a (C ₁ -C ₆₎ alkylsulfonyl group, R ³ is a hydrogen atom, (C ₁ -C ₆₎ alkyl group, ( C ₁ -C ₆₎ alkoxy group, or a halogen atom,

[0008]

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[0009] In addition to the nitrogen atom shown,
Having a heteroatom selected from oxygen, oxygen and nitrogen
5- or 6-membered nitrogen-containing heterocycle or benzo-fused thereof
Ring-type nitrogen-containing heterocycle (here, nitrogen-containing heterocycle or its base)
Nzo-fused ring type nitrogen-containing heterocycle is selected from substituent group α
Which may have any substituent). <Substituent group α> halogen atom, (C₁−C₆) Alkyl group, (C
_Two−C₆) Alkenyl group, (C_Two−C₆) Alkynyl group, (C_Three−C₆)
Cycloalkyl group, (C₁−C₆) Alkoxy group, (C_Two−C₆A)
Lucenyloxy group, (C_Two−C₆) Alkynyloxy group, (C₁
−C₆) Alkylthio group, (C₁−C₆) Alkylsulfinyl
Group, (C₁−C₆) Alkylsulfonyl group, (C₁−C₆) Alkyl
Carbonyl group, (C₁−C₆) Alkoxycarbonyl group, (C₁
−C_Four) Alkoxy (C₁−C_Four) Alkyl group, (C₁−C_Four) Haloa
Alkyl group, (C₁−C_Four) Haloalkoxy group, phenyl group
[The group is a halogen atom, (C₁−C_Four) Alkyl group or (C₁−C
_Four) May be substituted with an alkoxy group], a benzyl group
[The group is a halogen atom, (C₁−C_Four) Alkyl group or (C ₁−C
_Four) May be substituted with an alkoxy group], phenoxy
Group [the group is a halogen atom, (C₁−C_Four) Alkyl group or (C₁
−C_Four) May be substituted with an alkoxy group], benzo
Yl group [the group is a halogen atom, (C₁−C_Four) Alkyl group or
(C₁−C_Four) May be substituted with an alkoxy group],
Group, mono (C₁−C_Four) Alkylamino group, di (C₁−C_Four) Al
Shown by killamino group, oxo group, cyano group, nitro group
Pyrimidine or triazine derivatives and (2) these
It is a fungicide for agricultural and horticultural use which contains as an active ingredient.

[0010] The symbols and terms described in this specification will be described.

In this specification, for example, "C _1-
The notation such as “C ₆ ” indicates that the number of carbon atoms of the substituent that follows is 1 to 6 in this case.

The halogen atom means a fluorine atom, a chlorine atom, a bromine atom or an iodine atom.

The (C ₁ -C ₆ ) alkyl group means a linear or branched alkyl group, for example, a methyl group, an ethyl group,
-Propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-
Examples include a pentyl group, an isopentyl group, a neopentyl group, an n-hexyl group, an isohexyl group, and a 3,3-dimethylbutyl group.

The (C ₂ -C ₆ ) alkenyl group is a linear or branched alkenyl group, for example, a vinyl group, a 1-propenyl group, an allyl group, an isopropenyl group, a 1-butenyl group or a 2-alkyl group. Butenyl and the like.

The (C ₂ -C ₆ ) alkynyl group means a linear or branched alkynyl group such as ethynyl group, 1-propynyl group, 2-propynyl group, 1-butynyl group and 2-alkynyl group.
Butynyl group, 3-butynyl group, 4-methyl-1-pentynyl group, 3-methyl-1-pentynyl group and the like.

The (C ₃ -C ₆ ) cycloalkyl group includes, for example, a cyclopropyl group, a cyclopentyl group and a cyclohexyl group.

The (C ₁ -C ₄ ) haloalkyl group refers to a linear or branched alkyl group substituted by a halogen atom, such as a fluoromethyl group, a chloromethyl group, a bromomethyl group, a difluoromethyl group, Examples thereof include a dichloromethyl group, a dibromomethyl group, a trifluoromethyl group, a chlorodifluoromethyl group and a pentafluoroethyl group.

The (C ₁ -C ₆ ) alkoxy group is a linear or branched alkoxy group, for example, a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, an n-butoxy group, an isobutoxy group. , Sec-butoxy group, ter
Examples thereof include a t-butoxy group, an n-pentyloxy group, an isopentyloxy group, and an n-hexyloxy group.

The (C ₂ -C ₆ ) alkenyloxy group means a linear or branched alkenyloxy group, such as an allyloxy group, an isopropenyloxy group or a 2-butenyloxy group.

The (C ₂ -C ₆ ) alkynyloxy group means a linear or branched alkynyloxy group, such as a 2-propynyloxy group, a 2-butynyloxy group or a 3-butynyloxy group. it can.

The (C ₃ -C ₆ ) cycloalkoxy group includes, for example, a cyclopropyloxy group, a cyclopentyloxy group and a cyclohexyloxy group.

The (C ₁ -C ₄ ) haloalkoxy group refers to a straight-chain or branched-chain alkoxy group substituted by a halogen atom, such as fluoromethoxy, difluoromethoxy, trifluoromethoxy or pentamethoxy. And fluoroethoxy groups.

A cyano (C ₁ -C ₄ ) alkyloxy group is a straight-chain or branched (C ₁ -C ₄ ) substituted by a cyano group.
It represents an alkyloxy group and includes, for example, a cyanomethoxy group or a cyanoethoxy group.

(C ₁ -C ₄ ) alkoxy (C ₁ -C ₄ ) alkyloxy group means an alkyloxy group in which the alkoxy moiety has the above-mentioned meaning, for example, a methoxymethoxy group or an ethoxymethoxy group. Can be.

The (C ₁ -C ₄ ) alkoxy (C ₁ -C ₄ ) alkyl group refers to an alkyl group in which the alkoxy moiety has the above-mentioned meaning, such as a methoxymethyl group or an ethoxymethyl group. .

The (C ₃ -C ₆ ) cycloalkyl (C ₁ -C ₄ ) alkyloxy group means an alkyloxy group in which the cycloalkyl moiety has the above-mentioned meaning, and examples thereof include a cyclopropylmethoxy group. it can.

The (C ₁ -C ₆ ) alkylcarbonyl group refers to an alkylcarbonyl group in which the alkyl portion has the above-mentioned meaning, and examples thereof include an acetyl group.

The (C ₁ -C ₆ ) alkoxycarbonyl group refers to an alkoxycarbonyl group in which the alkyl moiety has the above-mentioned meaning, and examples thereof include a methoxycarbonyl group and an ethoxycarbonyl group.

The (C ₁ -C ₆ ) alkylthio group means a linear or branched alkylthio group, for example, a methylthio group,
Ethylthio, n-propylthio, isopropylthio, n-butylthio, isobutylthio, sec-butylthio, tert-butylthio, n-hexylthio and the like.

The (C ₁ -C ₆ ) alkylsulfinyl group means a group in which the alkyl moiety has the above-mentioned meaning, and includes methylsulfinyl, ethylsulfinyl, isopropylsulfinyl, butylsulfinyl, hexylsulfinyl and the like. be able to.

The (C ₁ -C ₆ ) alkylsulfonyl group means a group in which the alkyl moiety has the above-mentioned meaning, and includes groups such as methylsulfonyl group, ethylsulfonyl group, isopropylsulfonyl group, butylsulfonyl group, and hexylsulfonyl. I can give it.

The mono (C ₁ -C ₄ ) alkylamino group means a group in which the alkyl moiety has the above-mentioned meaning, and examples thereof include methylamino, ethylamino, isopropylamino, butylamino and the like.

The term "di (C ₁ -C ₄ ) alkylamino group" means a group having the same meaning as described above in which the alkyl portions may be the same or different, such as a dimethylamino group, a diethylamino group and a methylethylamino group. , A methylisopropylamino group, a dibutylamino group and the like.

[0034]

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The term "5- to 6-membered nitrogen-containing hetero ring which may have a hetero atom selected from a sulfur atom, an oxygen atom and a nitrogen atom in addition to the indicated nitrogen atom or a benzo-fused ring type thereof" Represents a nitrogen heterocycle, for example, imidazole,
Indole, indazole, triazole, benzotriazole, thiazolidine and the like can be mentioned.

[0036]

Next, specific examples of the compound of the present invention represented by the general formula [I] are shown in Tables 1 to 7. However, the compounds of the present invention are not limited to these compounds. The compound numbers will be referred to in the following description.

The symbols in the table have the following meanings.
Me represents a methyl group, Et represents an ethyl group, and P
r represents an n-propyl group, Pr-i represents an iso-propyl group, Bu represents an n-butyl group, and Bu-
i represents an iso-butyl group, and Bu-s represents sec-
A butyl group, Bu-t represents a tert-butyl group, Hex represents an n-hexyl group, Pr-c represents a cyclopropyl group, Pen-c represents a cyclopentyl group, and Hex- c represents a cyclohexyl group;
h represents a phenyl group, and Bn represents a benzyl group.
Further, for example, Ph (4-Cl) indicates a 4-chlorophenyl group, and Bn (4-Cl) indicates a 4-chlorobenzyl group.

[0038]

[Table 1]

[0039]

[Table 2]

[0040]

[Table 3]

[0041]

[Table 4]

[0042]

[Table 5]

[0043]

[Table 6]

[0044]

[Table 7]

Typical production methods of the pyrimidine derivative and the triazine derivative represented by the general formula [I], which are the compounds of the present invention, are illustrated below.

<Production Method 1>

[0047]

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(Wherein R ¹ , R ² , A and

[0049]

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Each represents the same meaning as described above, and L represents a leaving group such as a halogen atom, a lower alkylsulfonyl group, a benzylsulfonyl group, a phenylsulfonyl group or a p-toluenesulfonyl group. The compound of the present invention represented by the general formula [I] is represented by the general formula [II]:
And a pyrimidine derivative or a triazine derivative represented by the general formula [III] in a solvent in the presence of a base.

As the base used herein, for example,
Alkali metal carbonates such as sodium carbonate, potassium carbonate or lithium carbonate; alkali metal bicarbonates such as sodium bicarbonate or potassium bicarbonate; alkali metal acetates such as sodium acetate or potassium acetate; sodium methoxide or sodium ethoxide Alkali metal alcoholates such as lithium hydroxide, sodium hydroxide or potassium hydroxide; alkali metal hydrides such as sodium hydride or potassium hydride; alkaline earth metal carbonates such as calcium carbonate; Alkaline earth metal bicarbonates such as calcium hydrogen, alkaline earth metal acetates such as calcium acetate, or alkaline earth metal hydroxides such as calcium hydroxide or magnesium hydroxide can be used.

The solvent which can be used in this reaction may be any solvent which does not hinder the progress of this reaction, and includes, for example, ethers such as diethyl ether, diisopropyl ether, tetrahydrofuran, dioxane, monoglyme or diglyme; dichloroethane, chloroform, Halogenated hydrocarbons such as carbon chloride or tetrachloroethane; aromatic hydrocarbons such as benzene, chlorobenzene, nitrobenzene, toluene or xylene; amides such as N, N-dimethylformamide or N, N-dimethylacetamide; Imidazolines such as 3-dimethyl-2-imidazolinone; and sulfoxides such as dimethyl sulfoxide or sulfolane can be used, and these inert solvents can be used alone or as a mixture.

The reaction temperature varies depending on the starting compounds or reagents, but may be selected from the range from -20 ° C to the boiling point of the inert solvent used, and preferably from 0 ° C to the boiling point of the solvent.

The reaction time varies depending on the starting compound, reaction temperature, reaction amount, solvent and the like, but is usually 30 minutes to 72 hours, preferably 1 hour to 48 hours.

After the completion of the reaction, the desired product can be isolated from the reaction system by a conventional method and, if necessary, purified by column chromatography, recrystallization or the like.

<Manufacturing method 2>

[0057]

Embedded image

(Where A and

[0059]

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Represents the same meaning as described above, and Z represents a (C ₁ -C ₆ ) alkoxy group, a (C ₂ -C ₆ ) alkenyloxy group, a (C ₂ -C ₆ ) alkynyloxy group, a (C ₁ -C ₆ ) ₆ ) alkylthio group or di (C ₁
—C ₆ ) represents an alkylamino group. The compound of the present invention represented by the general formula [Ib] includes a pyrimidine derivative or a triazine derivative represented by the general formula [Ia] and an alcohol, a mercaptan or an amine represented by the general formula [IV]. Can be produced by reacting the compound with a solvent in the presence of a base without a solvent or in a suitable solvent.

As the base and solvent that can be used in this reaction, the bases and solvents exemplified in Production Method 1 can be used.

The reaction temperature varies depending on the starting compounds, reagents and the like, but may be selected from the range of -20 ° C. to the boiling point of the inert solvent used, preferably from 0 ° C. to the boiling point of the solvent. After completion, the desired product can be isolated from the reaction system by a conventional method, and can be purified by column chromatography, recrystallization or the like, if necessary.

<Production Example 1> 1- (4,6-Dimethoxypyrimidin-2-yl) benzotriazole (Compound No. 56) Benzotriazole (0.60 g) was dissolved in dimethylformamide (10 ml) and hydrogenated at room temperature. Sodium chloride (60% purity, oily, 0.22 g) was added. After stirring for 1 hour, 2-methylsulfonyl-4,6-dimethoxypyrimidine (1.1
g) was added at room temperature and stirred for 8 hours. Ice water was added to the reaction mixture, extracted with ethyl acetate, washed with brine, and dried over anhydrous magnesium sulfate. After evaporating the solvent, the residue was purified by silica gel column chromatography to obtain 0.90 g of the desired product as a white powder (melting point: 138 to 141 ° C).

<Production Example 2> 1- (4,6-Dichlorotriazin-2-yl) benzotriazole (Compound No. 25) Cyanuric chloride (3.1)
g) and sodium hydrogen carbonate (1.7 g) were dissolved in tetrahydrofuran (10 ml), and benzotriazole (2.0 g) was added at room temperature. After stirring for 3 hours, the reaction mixture was poured into water, extracted with ethyl acetate, washed with brine, and dried over anhydrous magnesium sulfate. After evaporation of the solvent, the residue was washed with isopropyl alcohol to give a white powder (melting point 221).
To 224 ° C.).

<Production Example 3> 1- (4,6-Diethoxytriazin-2-yl) benzotriazole (Compound No. 26) 1- (4,6-Dichlorotriazin-2-yl) benzotriazole (1.
0 g) was dissolved in 1,4-dioxane (60 ml), and sodium ethylate (0.51 g) was added thereto at room temperature.
Stirred at C for 2 hours. After completion of the reaction, the reaction solution was poured into water, extracted with ethyl acetate, washed with an aqueous citric acid solution and saturated saline, and then dried over anhydrous magnesium sulfate. After evaporating the solvent,
The residue was washed with isopropyl alcohol to obtain 3.8 g of the desired product as a white powder (melting point: 123 to 126 ° C).

The agricultural / horticultural fungicide of the present invention comprises a pyrimidine derivative or a triazine derivative represented by the general formula [I] as an active ingredient. When the compound of the present invention is used as an agricultural and horticultural fungicide, the active ingredient can be used in an appropriate dosage form according to the purpose. Normally, the active ingredient is diluted with an inert liquid or solid carrier, and if necessary, surfactants and other formulation auxiliaries are added thereto, and the formulation forms such as powders, wettable powders, emulsions, or granules Can be used with

Suitable carriers include solid carriers such as talc, bentonite, clay, kaolin, diatomaceous earth, white carbon, vermiculite, slaked lime, silica sand, ammonium sulfate or urea, and liquid carriers such as isopropyl alcohol, xylene, cyclohexanone or methylnaphthalene. And the like. As the surfactant and dispersant, for example, dinaphthyl methanesulfonate, alcohol sulfate, alkylaryl sulfonate, lignin sulfonate, polyoxyethylene glycol ether, polyoxyethylene alkylaryl ether or polyoxyethylene sorbitan Monoalkylates and the like.
Examples of the auxiliary include carboxymethyl cellulose. These preparations are diluted to an appropriate concentration and sprayed or applied directly.

The fungicide for agricultural and horticultural use of the present invention can be used by foliage application, soil application or water surface application. The compounding ratio of the active ingredient is appropriately selected according to need, but is 0.1 to 20% (by weight) in the case of powder and granules, and 5 to 80% (by weight) in the case of emulsion and wettable powder. Appropriate.

The application rate of the fungicide for agricultural and horticultural use of the present invention varies depending on the kind of the compound used, the target disease, the tendency of occurrence, the degree of damage, the environmental conditions, the dosage form used, and the like. For example, when used as is, such as powders and granules,
The active ingredient is suitably selected from the range of 0.1 g to 5 kg, preferably 1 g to 1 kg per 10 ares. Also,
When used in a liquid form such as an emulsion and a wettable powder, the amount is 0.1%.
1 ppm to 10,000 ppm, preferably 1 ppm to
It is preferable to appropriately select from the range of 3,000 ppm.

The compounds according to the invention can be used according to the above-mentioned application forms, for example, algal fungi (Omycetes), ascomycetes (Asc)
omycetes), deuteromycetes (Deuteromy)
cetes), and Basidiomycete
tes) can be controlled. Next, specific bacterial names are given as non-limiting examples. Genus Pseudoperonospora (Pseudoperonospora),
For example, cucumber downy mildew (Pseudoperonos)
pora cubensis, Erysife (Erys)
iphe), such as wheat powdery mildew (Erysi)
phe graminis, Venturia (Vent)
uria), for example, the scab of apple (Venturi)
a inaequalis), Pyricularia (Pyr)
icularia), for example, rice blast fungus (Pyr)
icularia oryzae, Botrytis (Bo)
trytis), for example, Botryt
is cinerea), Rhizoctonia (Rhizoc)
tonia) genus, for example, Rhizoct
onia solani), Puchinia (Puccin)
ia) genus, for example, wheat rust (Puccinia)
recondita).

Further, the compound of the present invention may be mixed with an insecticide, another fungicide, a herbicide, a plant growth regulator or a fertilizer, if necessary. Next, the formulation method will be specifically described with reference to typical formulation examples of the agricultural and horticultural fungicides of the present invention. In the following description, “%” indicates weight percentage.

Formulation Example 1 Dust 2% of the compound of the present invention (Compound No. 17), 5% of diatomaceous earth and 93% of clay were uniformly mixed and pulverized to give a dust.

Formulation Example 2 Wettable powder 50% of the compound of the present invention (Compound No. 23), diatomaceous earth 45
%, Sodium dinaphthylmethanedisulfonate 2% and sodium ligninsulfonate 3% were uniformly mixed and pulverized to obtain a wettable powder.

Formulation Example 3 Emulsion 30% of the compound of the present invention (Compound No. 47), 20% of cyclohexanone, 11% of polyoxyethylene alkylaryl ether, calcium alkylbenzene sulfonate 4
% And methylnaphthalene 35% were uniformly dissolved to form an emulsion.

Formulation Example 4 Granules 5% of the compound of the present invention (Compound No. 55), 2% of sodium salt of lauryl alcohol sulfate, 5% of sodium ligninsulfonate, 2% of carboxymethylcellulose
And 86% of clay are uniformly mixed and pulverized. The mixture was kneaded by adding an amount equivalent to 20% of water, processed into granules of 14 to 32 mesh using an extrusion granulator, and then dried to obtain granules.

Next, the effects of the fungicide for agricultural and horticultural use of the present invention will be specifically described with reference to test examples.

Test Example 1 Wheat Powdery Mildew Prevention Effect Test Wheat seeds (cultivar: 9 cm × 9 cm)
Agriculture No. 61) was sown in a batch of 9 grains, grown in a greenhouse for 8 days, diluted with water so that the active ingredient concentration became 500 ppm, and the wettable powder prepared according to Formulation Example 2 was diluted with water to 10 ppm.
ml. After air drying, wheat powdery mildew (Erys)
iphe graminis), and inoculate 20 to 20
Placed in a greenhouse at 25 ° C. 10 days after inoculation
The diseased area of the leaves was investigated and evaluated according to the criteria in Table 8. The results are shown in Table 9.

[0078]

[Table 8]

[0079]

[Table 9]

[0080]

The agricultural and horticultural fungicides of the present invention have a broad antibacterial spectrum, and exhibit an excellent effect against wheat powdery mildew. Furthermore, it has a high control effect on cucumber downy mildew, apple scab, rice blast, cucumber gray mold, rice sheath blight and wheat leaf rust, and has no residual effects on crops without causing phytotoxicity. It is also useful as a fungicide for agricultural and horticultural use because it also has the characteristics of excellent resistance and rain resistance.

 ──────────────────────────────────────────────────続 き Continuing from the front page (72) Inventor Kenji Ando 408-1, Shioda, Fukuda-cho, Iwata-gun, Shizuoka Prefecture Inside of K-I Research Institute Inc. (72) Norihisa Yonekura Shioda, Fukuda-cho, Iwata-gun, Shizuoka 408-1 Kay Research Institute Co., Ltd. 4F term at 2384 Yasaka, Kakegawa-shi, Shizuoka 4H011 AA01 BB08 BB09 BC05 BC07 BC18 BC19 BC20 DA02 DA15 DA16 DH03

Claims (2)

[Claims] 1. A compound of the general formula [I]Ａ In the formula, A is a nitrogen atom or CR³And R¹And R
²Are independently a hydrogen atom, a halogen atom, (C₁−C₆)
Alkyl group, (C_Two−C₆) Alkenyl group, (C_Two−C₆) Alkini
Group, (C_Three−C₆) Cycloalkyl group, (C₁−C_Four) Haloalkyl
Group, (C₁−C₆) Alkoxy group, (C_Two−C₆) Alkenyloxy
Group, (C_Two−C₆) Alkynyloxy group, (C_Three−C₆) Cycloa
Alkoxy group, (C₁−C_Four) Haloalkoxy group, cyano (C₁−C
_Four) Alkyloxy group, (C₁−C_Four) Alkoxy (C₁−C_Four) Al
Killoxy group, (C_Three−C₆) Cycloalkyl (C₁−C_Four) Archi
Ruoxy group, benzyloxy group [the group is a halogen atom,
(C₁−C_Four) Alkyl group or (C₁−C_Four) Substituted with an alkoxy group
It may be. ], (C₁−C₆) Alkylthio group, pheno
A xy group [the group is a halogen atom, (C₁−C_Four) Alkyl group or
(C₁−C_Four) It may be substituted by an alkoxy group. ]
Enyl group, di (C₁−C_Four) Alkylamino group, cyano group or
(C₁−C₆) Represents an alkylsulfonyl group;³Is hydrogen field
Child, (C₁−C₆) Alkyl group, (C₁−C₆) Alkoxy group, or
Represents a halogen atom,Means sulfur atom, oxygen atom
5 which may have a heteroatom selected from a nitrogen atom and a nitrogen atom
6-membered nitrogen-containing heterocycle or its benzo-fused ring type nitrogen-containing
Heterocycle (here, nitrogen-containing heterocycle or its benzo-fused ring
Type nitrogen-containing heterocycle is an arbitrary substituent selected from substituent group α
Which may have a group). Pyrimidine or｝
Is a triazine derivative. <Substituent group α> halogen atom, (C₁−C₆) Alkyl group, (C
_Two−C₆) Alkenyl group, (C_Two−C₆) Alkynyl group, (C_Three−C₆)
Cycloalkyl group, (C₁−C₆) Alkoxy group, (C_Two−C₆A)
Lucenyloxy group, (C_Two−C₆) Alkynyloxy group, (C₁
−C₆) Alkylthio group, (C₁−C₆) Alkylsulfinyl
Group, (C₁−C₆) Alkylsulfonyl group, (C₁−C₆) Alkyl
Carbonyl group, (C₁−C₆) Alkoxycarbonyl group, (C₁
−C_Four) Alkoxy (C₁−C_Four) Alkyl group, (C₁−C_Four) Haloa
Alkyl group, (C₁−C_Four) Haloalkoxy group, phenyl group
[The group is a halogen atom, (C₁−C_Four) Alkyl group or (C₁−C
_Four) May be substituted with an alkoxy group], a benzyl group
[The group is a halogen atom, (C₁−C_Four) Alkyl group or (C ₁−C
_Four) May be substituted with an alkoxy group], phenoxy
Group [the group is a halogen atom, (C₁−C_Four) Alkyl group or (C₁
−C_Four) May be substituted with an alkoxy group], benzo
Yl group [the group is a halogen atom, (C₁−C_Four) Alkyl group or
(C₁−C_Four) May be substituted with an alkoxy group],
Group, mono (C₁−C_Four) Alkylamino group, di (C₁−C_Four) Al
Killamino group, oxo group, cyano group, nitro group 2. A fungicide for agricultural and horticultural use comprising the pyrimidine or triazine derivative according to claim 1 as an active ingredient.