JP2000198785A - Pyrazolopyrimidine derivative and its application - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a new compound having excellent plant disease controlling activity against Pyricularia oryzae of rice plant, Cladosporium fulvum of cucumber, Sphaerotheca fuliginea of cucumber or the like. SOLUTION: A compound of formula I [R1 and R2 are each H or methyl; R3 is a 3-8C cycloalkyl, a (substituted) 1-10C alkyl, a (substituted) phenyl or the like; here, when R1 is methyl and R3 is a non-substituted phenyl, R2 is methyl], for example, 4-(3-chlorophenyl)methyl-7-methylpyrazolo[1,5-a]pyrimidin-3-yl cyanide. The compound of formula I is obtained by reacting a compound of formula II (L is an eliminable group), [e.g. 2-(dimethylamino)-1-(2-(3-chlorophenyl) acetyl)-1-ethenyl cyanide] with a compound of formula III, [e.g. (5-methyl-1H- pyrazol-3-yl)amine] preferably at a molar ratio of 1:(1.1-2), commonly in a solvent such as acetic acid, commonly at 50-120 deg.C.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

TECHNICAL FIELD The present invention relates to a pyrazolopyrimidine compound and a plant disease controlling agent containing the same as an active ingredient.

[0002]

An object of the present invention is to provide a compound having an excellent plant disease controlling effect.

[0003]

Means for Solving the Problems The present inventors have conducted intensive studies to find an excellent plant disease controlling agent. As a result, a pyrazolopyrimidine derivative represented by the following general formula 2 shows an excellent plant disease controlling effect. Have been found, and the present invention has been accomplished. That is, the present invention provides a compound represented by the general formula:

Embedded image[Wherein, R¹And R^TwoAre the same or different hydrogen atoms or
Represents a methyl group;^ThreeIs C3-C8 cycloalkyl
Group, an optionally substituted C1-C10 alkyl group,
Optionally substituted phenyl group, optionally substituted
Naphthyl group, monocyclic aromatic heterocyclic ring which may be substituted
Group or monocyclic non-aromatic heterocyclic group which may be substituted
Represents Where R¹Is a methyl group and R^ThreeIs replaced
Is not a phenyl group, ^TwoIs a methyl group
You. And a pyrazolopyrimidine derivative represented by
It is referred to as an invention compound. ) And the compound as an active ingredient.
And a plant disease controlling agent having the same.

[0004]

BEST MODE FOR CARRYING OUT THE INVENTION First, a pyrazolopyrimidine derivative represented by the general formula 8 will be described. In the compound of the present invention, R ¹ and R ² are the same or different and represent a hydrogen atom or a methyl group. The C3~C8 cycloalkyl group represented by R ^3, for example, cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group and the like. Examples of the substituent in the C1 to C10 alkyl group which may be substituted include, for example, a halogen atom (a fluorine atom, a chlorine atom, a bromine atom, an iodine atom) and an alkoxy group (for example,
Methoxy group, ethoxy group, propyloxy group, etc.), alkylthio group (eg, methylthio group, ethylthio group, etc.), phenoxy group, phenylthio group, cyano group, alkoxycarbonyl group (eg, methoxycarbonyl group,
Ethoxycarbonyl group), alkylamino group (eg, methylamino group, ethylamino group, dimethylamino group, diethylamino group, etc.), 1-pyrrolidinyl group, piperidino group, morpholino group, allyloxy group, propargyloxy group and the like. At least one substituent may be mentioned, where two or more substituents may be the same or different. C1 to C1 in the optionally substituted C1 to C10 alkyl group
Examples of the 0 alkyl group include a methyl group, an ethyl group,
Propyl, isopropyl, butyl, isobutyl, s-butyl, t-butyl, pentyl, isopentyl, s-pentyl, neopentyl, hexyl, heptyl, octyl, nonyl, decyl And the like. Examples of the substituent in the optionally substituted phenyl group and the optionally substituted naphthyl group include, for example, a halogen atom (eg, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom), an alkyl group (eg, a methyl group, C such as ethyl group, propyl group and i-propyl group
1-C3 alkyl group, etc.), alkoxy group (for example, C1-C4 alkoxy group such as methoxy group, ethoxy group, propyloxy group, isopropyloxy group, butyloxy group, etc.), cyano group, nitro group, haloalkyl group (for example, trifluoro group) Methyl group, trichloromethyl group, etc.), haloalkoxy group (eg, C1 to C2 haloalkoxy group such as trifluoromethoxy group, tetrafluoroethoxy group, etc.), phenoxy group, alkylene group (eg, trimethylene group, tetramethylene group, etc.) And at least one substituent selected from an alkylenedioxy group (for example, a methylenedioxy group, an ethylenedioxy group and the like). When two or more substituents are present, the substituents are the same. Or may be different, a divalent group such as an alkylene group or an alkylenedioxy group Substituting adjacent carbon atoms on the benzene ring. Examples of the naphthyl group in the optionally substituted naphthyl group include a 1-naphthyl group and a 2-naphthyl group. Examples of the substituent in the monocyclic aromatic heterocyclic group which may be substituted and the monocyclic non-aromatic heterocyclic group which may be substituted include, for example, a halogen atom (for example, a fluorine atom, a chlorine atom, a bromine atom, Iodine atom, etc.), alkyl group (eg, methyl group, ethyl group,
A C1 to C3 alkyl group such as a propyl group and an isopropyl group), an alkoxy group (for example, a methoxy group, an ethoxy group,
At least one substituent selected from a C1 to C4 alkoxy group such as a propyloxy group, an isopropyloxy group and a butyloxy group), a cyano group, a nitro group and the like, wherein two or more substituents are present And the substituents may be the same or different. Examples of the monocyclic aromatic heterocyclic group in the optionally substituted monocyclic aromatic heterocyclic group include a 2-furyl group, a 3-furyl group,
2-thienyl group, 3-thienyl group, 4-thiazolyl group,
2-pyridyl group, 3-pyridyl group, 4-pyridyl group, and the like, and examples of the monocyclic non-aromatic heterocyclic group in the optionally substituted monocyclic non-aromatic heterocyclic group include: Examples thereof include a 2-tetrahydrofuryl group and a 2-tetrahydropyranyl group.

Next, a method for producing the compound of the present invention will be described. The compound of the present invention has the general formula

Embedded image (Wherein, R ³ has the same meaning as described above, and L represents a leaving group.)

Embedded image (Wherein, R ¹ and R ² have the same meanings as described above). As the leaving group represented by L in the above formula 9, for example, N (R ⁶ ) R ⁷ (where R
⁶ and R ⁷ are the same or different and represent a lower alkyl group, or R ⁶ and R ⁷ together represent an alkylene group or an alkyleneoxyalkylene group. And R ⁶ and R ⁷ are, for example, a methyl group, an ethyl group, n
-Propyl group, i-propyl group, n-butyl group and the like. Specific examples of the leaving group include N, N-dimethylamino, N, N-diethylamino, N, N-dipropylamino, N, N-diisopropylamino, N, N-diisopropylamino,
Examples include an N-dibutylamino group, an N-methyl-N-propylamino group, an N-methyl-N-propylamino group, a 1-pyrrolidinyl group, a piperidino group, and a morpholino group. Although the reaction can be carried out without a solvent, it is usually carried out in a solvent, and as a solvent to be used, alcohols such as methanol, ethanol, n-propanol, i-propanol and n-butanol, formic acid, acetic acid and propionic acid And the like. The reaction temperature range of the reaction is usually 50 ° C to 120 ° C. The amount of the reagent used in the reaction is usually 1 to 3 moles, preferably 1.1 to 1 mole of the pyrazolylamine compound represented by the general formula (1) per mole of the cyanide compound represented by the general formula (9). 2 mole ratio. After completion of the reaction, the compound of the present invention can be usually obtained by pouring the reaction solution into water and performing ordinary post-treatment operations such as extraction with an organic solvent and concentration. The compound can also be purified by operations such as washing with an organic solvent, recrystallization, and column chromatography.

A cyan compound represented by the following general formula (9):
For example, Synthetic Communication
on, 1977, Vol. 7, No. 4, pp. 313-319 or J. Org. Prakt Chem 1990, 322,
No. 6, p. 977. The pyrazolylamine compound represented by the general formula (10) is described, for example, in Beilstein, Vol.
It can be produced according to the method described on page 33.

When the compound of the present invention is used as an active ingredient of a plant disease controlling agent, it may be used as it is without adding any other components, but it is usually used as a solid carrier, a liquid carrier, a surfactant, and other auxiliary agents for pharmaceuticals. Mix, emulsion, wettable powder,
It is formulated into suspensions, powders, granules, etc. and used. In these preparations, the compound of the present invention as an active ingredient is usually added in a weight ratio.
The content is 0.1 to 99.9%, preferably 1 to 90%.

[0008] Examples of the solid carrier used in the formulation include kaolin clay, attapulgite clay, bentonite, acid clay, pyrophyllite,
Talc, diatomaceous earth, calcite, corn cob flour, walnut shell flour, urea, ammonium sulfate, fine powders or granular materials such as synthetic hydrous silicon oxide, etc., and liquid carriers such as xylene, methyl naphthalene, etc. Examples thereof include hydrogens, alcohols such as isopropanol, ethylene glycol and cellosolve, ketones such as acetone, cyclohexanone and isophorone, vegetable oils such as soybean oil and cottonseed oil, dimethyl sulfoxide, acetonitrile, and water. Examples of the surfactant include anions such as alkyl sulfate, alkyl (aryl) sulfonate, dialkyl sulfosuccinate, polyoxyethylene alkyl aryl ether phosphate, and naphthalenesulfonic acid formalin condensate. Examples of the surfactant include nonionic surfactants such as surfactants, polyoxyethylene alkyl ethers, polyoxyethylene alkyl polyoxypropylene block copolymers, and sorbitan fatty acid esters.

[0009] Pharmaceutical adjuvants include, for example, lignin sulfonate, alginate, polyvinyl alcohol, gum arabic, CMC (carboxymethyl cellulose),
PAP (acidic isopropyl phosphate) and the like. Methods for applying the compound of the present invention include foliage application, soil treatment,
Seed disinfection and the like, and further, it can be used for any application method usually used by those skilled in the art.

When the compound of the present invention is used as an active ingredient of a plant disease controlling agent, the application rate of the active ingredient depends on the type of the target plant (crop etc.), the type of the target disease, the degree of occurrence of the disease,
Although it may vary depending on the form of formulation, application method, application time, weather conditions, etc., it is usually 0.01 to 50 g, preferably 0.05 to 10 g per arc. When the emulsion, wettable powder, suspending agent, etc. are diluted with water and applied, the application concentration is
0.0001-0.5%, preferably 0.0005-0.5%
0.2%, and dusts, granules and the like are applied without any dilution.

The compound of the present invention can be used as a plant disease controlling agent for fields, paddy fields, orchards, tea fields, pastures, lawns, etc., and can be used in combination with other plant disease controlling agents to provide a bactericidal effect. Can be expected to increase. Such other plant disease control agents include, for example, propiconazole, triazimenol, prochloraz, penconazole, tebuconazole, flusilazol, diniconazole, bromconazole, epoxyconazole, difenoconazole,
Cyproconazole, metconazole, triflumizole
, Azol-based fungicidal compounds such as fenpropimorph, tridemorph, and so on Cyclic amine fungicides such as fenpropidine, carbendazim, benomyl,
Benzimidazole bactericidal compounds such as thiabendazole and thiophanate methyl, procymidone, cyprodinil, pyrimethanil, dietofencarb, thiuram, fluazinam, mancozeb, iprodione, vinclozolin, chlorothalonil, captan, mepanipyrim, fenpiclonil, fludiclosonil.
Folpet, kresoxime methyl, azoxystrobin, N-methyl-α-methoxyimino-2-[(2,5
-Dimethylphenoxy) methyl] phenylacetamide, mepronil, flutranyl, penciclone, thifluzamide, flametopyr, fusalide, tricyclazole, pyroquilon, hinozan, chitazine P, fenhexamide, famoxadone, iprovalicarb, phenamidone, carpropamide, acibenzolar-S-methyl, carboxy , Probenazole, diclosimet and the like. Further, it can be mixed or used in combination with an insecticide, acaricide, a nematicide, a herbicide, a plant growth regulator, and a fertilizer.

Plant diseases which can be controlled by the compounds of the present invention include, for example, the following diseases. Rice blast (Pyricularia oryzae), sesame leaf blight (Cochliobolus miyabeanus), sheath blight (Rhizoc)
tonia solani, wheat powdery mildew (Erysiphe grami)
nis), Fusarium head blight (Gibberella zeae), Rust (Puccinia
striiformis, P. graminis, P. recondita, P. horde
i), snow rot (Typhula sp., Micronectriella nivalis),
Nude smut (Ustilago tritici, U. nuda), black smut (Tilletia caries), eye spot disease (Pseudocercosporella h)
erpotrichoides), scald disease (Rhynchosporium secalis),
Leaf blight (Septoria tritici), Fusarium wilt (Leptosphaeria)
nodorum), citrus black spot (Diaporthe citri), scab (Elsinoe fawcetti), fruit rot (Penicillium)
digitatum, P. italicum), Monilia disease of apples (Scler
otinia mali), rot (Valsa mali), powdery mildew (Po
dosphaera leucotricha), spot leaf spot (Alternaria mal
i), scab (Venturiainaequalis), pear scab (Ven
turia nashicola, V. pirina), black spot (Alternaria ki
kuchiana), scab (Gymnosporangium haraeanum), peach scab (Sclerotinia cinerea), scab (Cladospo)
rium carpophilum), Phomopsis rot
p.), grape black rot (Elsinoe ampelina), late rot (Glomerella cingulata), powdery mildew (Uncinula neca)
tor), rust (Phakopsora ampelopsidis), black lot disease (Guignardia bidwellii), downy mildew (Plasmopara)
viticola), oyster anthracnose (Gloeosporium kaki), leaf rot (Cercospora kaki, Mycosphaerella nawae), cucumber anthracnose (Colletotrichum lagenarium), powdery mildew (Sphaerotheca fuliginea), vine blight (Mycosphaerella)
melonis), Fusarium oxysporum, Downy mildew (Ps
eudoperonospora cubensis), plague (Phytophthoras
p.), seedling wilt (Pythium sp.), tomato ring rot (Altern
aria solani), leaf mold (Cladosporium fulvum), plague (Phytophthora infestans), eggplant brown spot (Phomopsis)
vexans), powdery mildew (Erysiphe cichoracearum), black spot on cruciferous vegetables (Alternaria japonica), white spot (Cercosporella brassicae), rust on spring onion (Puccinia)
allii), soybean purpura (Cercospora kikuchii), black spot (Elsinoe glycines), black spot (Diaporthe phase)
olorum var. sojae), bean anthracnose (Colletotrich)
um lindemthianum), black rot of peanuts (Cercospora)
personata), brown spot (Cercospora arachidicola), pea powdery mildew (Erysiphepisi), potato summer blight (Alternaria solani), blight (Phytophthora infesta)
ns), strawberry powdery mildew (Sphaerotheca humuli), tea net blast (Exobasidium reticulatum), white scab (Elsi
noe leucospila), tobacco scab (Alternarialongipe)
s), powdery mildew (Erysiphe cichoracearum), anthracnose (C
olletotrichumtabacum), downy mildew (Peronospora tabacin)
a), plague (Phytophthora nicotianae), sugar beet brown spot (Cercospora beticola), rose scab (Diplocarpo)
n rosae), powdery mildew (Sphaerotheca pannosa), chrysanthemum leaf spot on chrysanthemum (Septoria chrysanthemi-indici), white rust (Puccinia horiana), gray mold on various crops (Botry)
tis cinerea), sclerotium disease (Sclerotinia sclerotiorum) and the like.

[0013]

EXAMPLES The present invention will be described in more detail with reference to Production Examples, Preparation Examples, Test Examples, etc., but the present invention is not limited to these Examples. The compound numbers are indicated by the compound numbers described in Tables 1 to 28 below. First, Production Examples of the compound of the present invention will be shown.

Production Example 1 Production of 4- (3-chlorophenyl) methyl-7-methylpyrazolo [1,5-a] pyrimidin-3-yl cyanide (Compound 1-5) Step 1: 5.0 g of 3-chlorophenylacetic acid ( 30mmo
l) was dissolved in MeOH (60 ml), and 5.5 g (46 mmol) of thionyl chloride was added dropwise under ice cooling. After completion of the dropwise addition, the reaction solution was allowed to stand in a water bath for about 15 hours, and then the solvent was distilled off under reduced pressure. Toluene (30 ml) was added to the residue, and the solvent was again distilled off under reduced pressure to obtain 5.6 g of methyl 3-chlorophenylacetate. Step 2: 4.7 g of methyl 3-chlorophenylacetate (25%
mmol), 5.0 g of acetonitrile (121 mmol)
l), 1.1 g (27 mmol) of 60% oily sodium hydride was slowly added to a solution of toluene (40 ml) at room temperature, and the mixture was stirred at room temperature for 30 minutes. Thereafter, the reaction temperature was raised to 60 ° C., and the mixture was stirred for 1 hour.
Stirred for hours. Thereafter, the reaction mixture cooled to room temperature was poured into a separating funnel containing ice, and the aqueous layer was separated. 2N hydrochloric acid was added to the aqueous layer to make the solution acidic, and the mixture was extracted with ethyl acetate. After the organic layer was dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure, and the residue was subjected to silica gel column chromatography (elution solvent: hexane / ethyl acetate =
3/1) to give 2.3 g of 3- (3-chlorophenyl) -2-oxopropyl cyanide. Yield: 46% Step 3: 2.00 g (10 mmol) of 3- (3-chlorophenyl) -2-oxopropyl cyanide was dissolved in chloroform (5 ml) and cooled with ice water. 1.55 g (13 mmol) of N, N-dimethylformamide dimethyl acetal was slowly added dropwise to the solution. After completion of the dropwise addition, cooling was continued for 1 hour, and then the mixture was stirred at room temperature for 1 hour. The reaction solution was concentrated under reduced pressure, and hexane was added to the residue. The resulting solid was pulverized and collected by filtration to give 2- (dimethylamino) -1- (2- (3-chlorophenyl) acetyl)-.
1.87 g of 1-ethenyl cyanide was obtained. Yield 75% Step 4: (5-methyl-1H-pyrazol-3-yl)
0.11 g (1.13 mmol) of amine was added to acetic acid (2 m
1) and 2- (dimethylamino) -1-
0.20 g (0.93 mmol) of (2- (3-chlorophenyl) acetyl) -1-ethenyl cyanide was added,
Heat at 80 ° C. for 3 hours. After the reaction solution was cooled to room temperature, 10 ml of water was added, and this was extracted with 10 ml of ethyl acetate. The organic layer was washed successively with water and a 10% aqueous potassium carbonate solution, dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure, and the residue was subjected to silica gel column chromatography (elution solvent: hexane / ethyl acetate = 2/9).
1), 4- (3-chlorophenyl) methyl-7-
Methylpyrazolo [1,5-a] pyrimidin-3-yl
0.18 g of cyanide was obtained. 78% yield

Preparation Example 2 Preparation of 4- (3-methylphenyl) methyl-7-methylpyrazolo [1,5-a] pyrimidin-3-yl cyanide (Compound 1-9) Step 1: 3- (3-methylphenyl) 1.) 1.30 g (7.5 mmol) of 2-oxopropyl cyanide was dissolved in chloroform (5 ml) and cooled with ice water. 1.8 g (15 mmol) of N, N-dimethylformamide dimethyl acetal was slowly dropped into this solution. After completion of the dropwise addition, cooling was continued for 1 hour, and then the mixture was stirred at room temperature for 1 hour. The reaction solution is concentrated under reduced pressure, and the residue is subjected to silica gel chromatography (elution solvent: hexane / ethyl acetate = 1 /
1) and 2- (dimethylamino) -1- (2- (3
0.98 g of -methylphenyl) acetyl) -1-ethenyl cyanide were obtained. Yield 57% Step 2: (5-methyl-1H-pyrazol-3-yl)
0.80 g (8.24 mmol) of amine was added to acetic acid (10 m
1) and 2- (dimethylamino) -1-
0.95 g (4.20 mmol) of (2- (3-methylphenyl) acetyl) -1-ethenyl cyanide was added,
Heat at 60 ° C. for 3 hours. After the reaction solution was cooled to room temperature, 50 ml of water was added, and this was extracted with 50 ml of ethyl acetate. The organic layer was washed successively with water and a 10% aqueous potassium carbonate solution, dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure, and the residue was subjected to silica gel column chromatography (elution solvent: hexane / ethyl acetate = 2/9).
1), 4- (3-methylphenyl) methyl-7-
Methylpyrazolo [1,5-a] pyrimidin-3-yl
0.57 g of cyanide was obtained. Yield 52%.

Production Example 3 Production of 4- (2-fluorophenyl) methyl-7-methylpyrazolo [1,5-a] pyrimidin-3-yl cyanide (Compound 1-1) Step 1: 3- (2-fluorophenyl) 1.) 1.80 g (10.1 mmol) of 2-oxopropyl cyanide was dissolved in chloroform (7 ml) and cooled with ice water. 2.4 g (20 mmol) of N, N-dimethylformamide dimethyl acetal was slowly added dropwise to the solution. After completion of the dropwise addition, cooling was continued for 1 hour, and then the mixture was stirred at room temperature for 1 hour. The reaction solution was concentrated under reduced pressure, and hexane was added to the residue. The resulting solid is pulverized and collected by filtration to give 2- (dimethylamino) -1- (2- (2-fluorophenyl) acetyl).
1.79 g of -1-ethenyl cyanide was obtained. Yield 7
5.9% Step 2: (5-methyl-1H-pyrazol-3-yl)
Amine 1.0 g (10.3 mmol) was added to acetic acid (10 m
1) and 2- (dimethylamino) -1-
1.16 g (5.0 mmol) of (2- (2-fluorophenyl) acetyl) -1-ethenyl cyanide was added,
Heat at 60 ° C. for 3 hours. After the reaction solution was cooled to room temperature, 50 ml of water was added, and this was extracted with 50 ml of ethyl acetate. The organic layer was washed successively with water and a 10% aqueous potassium carbonate solution, dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure, and the residue was subjected to silica gel column chromatography (elution solvent: hexane / ethyl acetate = 3/9).
1), 4- (2-fluorophenyl) methyl-7
0.34 g of -methylpyrazolo [1,5-a] pyrimidin-3-yl cyanide was obtained. Yield 26%.

Production Example 4 4- (4-Chlorobutyl) -7-methylpyrazolo [1,
5-a] Pyrimidin-3-yl cyanide (Compound 1-
Production of 103) Step 1: 3- (diethylamino) -2-propenenitrile 4.22 g (34.0 mmol) and pyridine 3.00
g (38.0 mmol) in acetonitrile (40 ml)
And cooled with ice water. 5.5 g (35.4 mmol) of 5-chlorovaleric chloride was slowly added dropwise to the solution. After dropping, continue cooling for 1 hour and then at room temperature for 1 hour.
Stirred for hours. The reaction solution was concentrated under reduced pressure, 100 ml of 1N aqueous hydrochloric acid was poured into the residue, and 100 ml of ethyl acetate was added.
Extracted. The organic layer was washed with water, dried over anhydrous magnesium sulfate, the solvent was removed under reduced pressure, and the residue was subjected to silica gel column chromatography (elution solvent: hexane / ethyl acetate = 1/1) to give 1- 5.1 g of (5-chloropentanoyl) -2- (diethylamino) -1-ethenyl cyanide were obtained. Yield 61%. Step 2: (5-methyl-1H-pyrazol-3-yl)
2.0 g (20.6 mmol) of amine was added to ethanol (3
0 ml), and 5.1 g (21.0 mmol) of 1- (5-chloropentanoyl) -2- (diethylamino) -1-ethenylcyanide was added to the solution.
Heated for hours. After the reaction solution was cooled to room temperature, water 150
Then, the resulting mixture was extracted with 100 ml of ethyl acetate. The organic layer was washed successively with water and a 10% aqueous potassium carbonate solution, dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure, and the residue was subjected to silica gel column chromatography (elution solvent: hexane / ethyl acetate = 3/9). 1), 4- (4-chlorobutyl) -7-methylpyrazolo [1,5-a] pyrimidin-3-ylcyanide 3.6
0 g was obtained. Yield 70%.

Production Example 5 Production of 4- (4-methoxybutyl) -7-methylpyrazolo [1,5-a] pyrimidin-3-yl cyanide (Compound 1-105) 28% methanol solution of sodium methoxide in a flask 1 .20 g (6.22 mmol) and methanol (5
ml) and cooled with ice water. 0.80 g (3.21 mmol) of 4- (4-chlorobutyl) -7-methylpyrazolo [1,5-a] pyrimidin-3-ylcyanide was added to the solution.
l) was added and cooling continued for 1 hour, after which the solution was heated to reflux for 1 hour. The reaction solution was concentrated under reduced pressure, 1N hydrochloric acid (50 ml) was added to the residue, and the mixture was extracted with ethyl acetate (30 ml). After the organic layer was washed with water and dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure, and the residue was subjected to silica gel column chromatography (elution solvent: hexane / ethyl acetate = 2/1) to give a residue. -(4-methoxybutyl) -7-methylpyrazolo [1,5-a] pyrimidine-
0.07 g of 3-yl cyanide was obtained. 9% yield.

Preparation Example 6 Preparation of 4- (5-bromopentyl) -7-methylpyrazolo [1,5-a] pyrimidin-3-yl cyanide (Compound 1-117) Step 1: 25.0 g of cyanoacetic acid ( 0.29m
ol) and 43.6 g of ethyl orthoformate (0.29 mol)
l) and 20.9 g (0.29 g) of pyrrolidine under water cooling.
mol) was added dropwise. After completion of the dropwise addition, the reaction solution was heated at 90 ° C. for 2 hours. The reaction solution was concentrated under reduced pressure, and the residue was subjected to silica gel column chromatography (elution solvent: hexane / ethyl acetate = 2/1) to obtain 13.8 g of 3- (1-pyrrolidyl) -2-propenenitrile. . Yield 3
8%. Step 2: 3.17 g (26.0 mmol) of 3- (1-pyrrolidyl) -2-propenenitrile and 2.40 of pyridine
g (30.3 mmol) in acetonitrile (30 ml)
And cooled with ice water. 6.00 g (28.1 mmol) of 6-bromohexanoyl chloride was slowly added dropwise to the solution. After completion of the dropwise addition, cooling was continued for 1 hour, and then the mixture was stirred at room temperature for 1 hour. The reaction solution was concentrated under reduced pressure, 100 ml of 1N hydrochloric acid was added to the residue, and the mixture was extracted with 100 ml of ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, the solvent was removed under reduced pressure, and the residue was subjected to silica gel column chromatography (elution solvent: hexane / ethyl acetate = 1/1) to give 1-
(6-bromohexanoyl) -2- (1-pyrrolidyl)
5.3 g of -1-ethenyl cyanide was obtained. Yield 68
%. Step 3: (5-methyl-1H-pyrazol-3-yl)
1.75 g (18.0 mmol) of amine was dissolved in ethanol (30 ml), and 1- (5-bromohexanoyl) -2- (diethylamino) -1-ethenyl was added to the solution.
Add 5.3 g (17.7 mmol) of cyanide, and add
For 3 hours. After cooling the reaction solution to room temperature, water 1
50 ml was added, and this was extracted with 100 ml of ethyl acetate. The organic layer was washed successively with water and a 10% aqueous potassium carbonate solution, dried over anhydrous magnesium sulfate, the solvent was removed under reduced pressure, and the residue was subjected to silica gel column chromatography (elution solvent: hexane / ethyl acetate = 2/1). ) To give 4- (5-bromopentyl) -7-methylpyrazolo [1,5-a] pyrimidin-3-ylcyanide.
90 g were obtained. Yield 35%.

The above-mentioned production examples and examples of the compounds of the present invention which can be produced according to them are shown in Tables 1 to 28 below.

[0021]

Embedded image (Tables 1 to 7).

[Table 1]

[0022]

[Table 2]

[0023]

[Table 3]

[0024]

[Table 4]

[0025]

[Table 5]

[0026]

[Table 6]

[0027]

[Table 7]

[0028]

Embedded image (Tables 8 to 14).

[Table 8]

[0029]

[Table 9]

[0030]

[Table 10]

[0031]

[Table 11]

[0032]

[Table 12]

[0033]

[Table 13]

[0034]

[Table 14]

[0035]

Embedded image (Tables 15 to 21).

[Table 15]

[0036]

[Table 16]

[0037]

[Table 17]

[0038]

[Table 18]

[0039]

[Table 19]

[0040]

[Table 20]

[0041]

[Table 21]

[0042]

Embedded image (Tables 22 to 28).

[Table 22]

[0043]

[Table 23]

[0044]

[Table 24]

[0045]

[Table 25]

[0046]

[Table 26]

[0047]

[Table 27]

[0048]

[Table 28]

Some physical properties of the compound are shown below. Here, the melting point is a value measured by an automatic melting point measuring apparatus,
MR data are δ (CDCl ₃ ) ppm values. Compound 1-1: mp. 152.8 ° C. 8.46 (1H, s), 7.37 (1H, td, J =
8.2 Hz), 7.3-7.2 (1H, m), 7.1-
7.0 (2H, m), 6.60 (1H, s), 4.75
(2H, s), 2.52 (3H, s). Compound 1-2: mp. 117.1 ° C 8.44 (1H, s), 7.4-7.2 (3H, m),
7.05-6.90 (1H, m), 6.62 (1H,
s), 4.71 (2H, s), 2.57 (3H, s). Compound 1-3: mp. 118.9 ° C 8.44 (1H, s), 7.57 (2H, dd, J = 1
0,8 Hz), 6.99 (2H, t, J = 8 Hz),
6.61 (1H, s), 4.68 (2H, s), 28.
44 (1H, s), 7.57 (2H, dd, J = 10,
8 Hz), 6.99 (2H, t, J = 8 Hz), 6.6.
1 (1H, s), 4.68 (2H, s), 2.57 (3
H, s). Compound 1-4: mp. 10.67 ° C. 8.47 (1H, s), 7.44 (1H, dd, J =
8.2 Hz), 7.3-7.0 (2H, m), 6.63
(1H, s), 4.86 (2H, s), 2.52 (3
H, s). Compound 1-5: mp. 118.3 ° C. 8.45 (1H, s), 7.57 (1H, s), 7.4
4 (1H, m), 7.3-7.2 (2H, m), 6.6
2 (1H, s), 4.69 (2H, s), 2.57 (3
H, s).

Compound 1-6: mp. 160.2 ° C. 8.44 (1H, s), 7.52 (2H, d, J = 9H)
z), 7.27 (2H, d, J = 9 Hz), 6.61 (1
H, s), 4.68 (2H, s), 2.57 (3H,
s). Compound 1-8: mp. 12.9.4 ° C. 8.45 (1H, s), 7.73 (1H, t, J = 2H)
z), 7.49 (1H, dd, J = 8, 2 Hz);
41 (1H, dd, J = 8, 2 Hz), 7.18 (1
H, t, J = 8 Hz), 6.62 (1H, s), 4.6
8 (2H, s), 2.57 (3H, s).

Compound 1-9: mp. 11.77 ° C. 8.46 (1H, s), 7.26-7.15 (2H,
m), 7.08 (1H, td, J = 8, 2 Hz), 6.
92 (1H, d, J = 8 Hz), 6.61 (1H,
s), 4.70 (2H, s), 2.52 (3H, s),
2.50 (3H, s). Compound 1-10: mp. 128.2 ° C. 8.42 (1H, s), 7.36 (2H, d, J = 2H)
z), 7.18 (1H, t, J = 8 Hz), 7.08
(1H, d, J = 8 Hz), 6.59 (1H, s),
4.67 (2H, s), 2.57 (3H, s), 2.3
1 (3H, s). Compound 1-11: mp. 138.9 ° C. 8.40 (1H, s), 7.47 (2H, d, J = 8H)
z), 7.10 (2H, d, J = 8 Hz), 6.58
(1H, s), 4.66 (2H, s), 2.56 (3
H, s), 2.28 (3H, s).

Compound 1-16: mp. 157.1 ° C 8.43 (1H, s), 7.45 (1H, dd, J =
8.2 Hz), 7.25 (1 H, t, J = 8 Hz),
7.0-6.8 (2H, m), 6.56 (1H, s),
4.68 (2H, s), 3.84 (3H, s), 2.5
2 (3H, s). Compound 1-17: mp. 97.4 ° C 8.41 (1H, s), 7.3-7.1 (3H, m),
6.80 (1H, dd, J = 8, 2 Hz), 6.59
(1H, s), 4.69 (2H, s), 3.77 (3
H, s), 2.56 (3H, s). Compound 1-18: mp. 134.4 ° C 8.41 (1H, s), 7.52 (2H, d, J = 8H)
z), 6.83 (2H, d, J = 8 Hz), 6.59
(1H, s), 4.65 (2H, s), 3.76 (3
H, s), 2.57 (3H, s). Compound 1-28: mp. 80.3 ° C 8.45 (1H, s), 7.93 (1H, s), 7.7
5 (1H, d, J = 8 Hz), 7.55 (1H, dd,
J = 8.2 Hz, 7.43 (1H, t, J = 8H)
z), 6.62 (1H, s), 4.76 (2H, s),
2.57 (3H, s). Compound 1-37: oil 8.40 (1H, s), 7.4-7.2 (2H, m),
7.04 (1H, td, J = 8, 2 Hz), 6.61
(1H, s), 4.89 (2H, s), 2.52 (3
H, s).

Compound 1-38: oil 8.88 (1H, s), 7.41 (2H, d, J = 8H)
z), 7.35-7.25 (1H, m), 6.65 (1
H, s), 5.07 (2H, s), 2.57 (3H,
s). Compound 1-40: mp. 144.2 ° C. 8.46 (1H, s), 7.69 (1H, d, J = 2H)
z), 7.42 (1H, dd, J = 8, 2 Hz), 7.
37 (1H, d, J = 8 Hz), 6.63 (1H, d, J = 8 Hz)
s), 4.66 (2H, s), 2.57 (3H, s). Compound 1-41: mp. 124.4 ° C. 8.45 (1H, s), 7.44 (1H, d, J = 2H)
z), 7.15 (1H, dd, J = 8, 2 Hz), 7.
06 (1H, d, J = 8 Hz), 6.63 (1H,
s), 4.79 (2H, s), 2.50 (3H, s). Compound 1-46: mp. 134.7 ° C 8.43 (1H, s), 7.07 (1H, s), 6.7
7 (2H, dd, J = 1 Hz), 6.56 (1H,
s), 4.65 (2H, s), 3.80 (3H, s),
3.74 (3H, s), 2.52 (3H, s). Compound 1-58: mp. 104.0 ° C 8.41 (1H, s), 7.45 (1H, s), 7.2
5 (2H, d, J = 2 Hz), 6.60 (1H, s),
4.73 (2H, s), 2.58 (3H, s).

Compound 1-63: mp. 61.8 ° C 8.41 (1H, s), 6.58 (1H, s), 3.3
9 (2H, t, J = 9 Hz), 2.51 (3H, s),
2.0-1.8 (2H, m), 1.6-1.4 (2H,
m), 0.96 (3H, t, J = 9 Hz). Compound 1-67: mp. 100.7 ° C 8.41 (1H, s), 6.57 (1H, s), 3.4
1 (3H, s), 2.52 (3H, s), 1.12 (9
H, s). Compound 1-68: oil 8.41 (1H, s), 6.58 (1H, s), 3.3
8 (2H, t, J = 8 Hz), 2.55 (3H, s),
2.0-1.8 (2H, m), 1.6-1.2 (6H,
m), 0.89 (3H, t, J = 8 Hz). Compound 1-71: mp. 44.8 ° C 8.41 (1H, s), 6.59 (1H, s), 3.3
8 (2H, t, J = 8 Hz), 2.55 (3H, s),
2.0-1.8 (2H, m), 1.6-1.1 (12
H, m), 0.88 (3H, t, J = 6 Hz). Compound 1-73: mp. 116.9 ° C. 8.40 (1H, s), 6.58 (1H, s), 3.2
7 (2H, d, J = 6 Hz), 2.55 (3H, s),
2.15 (1H, brs), 1.8-1.6 (5H,
m), 1.9-1.1 (5H, m).

Compound 2-1: mp. 114.6 ° C 8.52 (1H, s), 8.32 (1H, d, J = 2H)
z), 7.57 (2H, dd, J = 8, 2 Hz), 7.
4-7.2 (3H, m), 6.83 (1H, d, J = 2
Hz), 4.77 (2H, s). Compound 3-1: mp. 11.42 ° C. 8.36 (1H, s), 7.56 (2H, dd, J =
8.2 Hz), 7.4-7.2 (3H, m), 4.69
(2H, s), 2.50 (3H, s), 2.27 (3
H, s) Compound 1-32: mp. 123.8 ° C 8.42 (1H, s), 7.4-7.2 (5H, m),
7.11 (1H, t, J = 8 Hz), 6.98 (2H,
d, J = 8 Hz), 6.97-6.85 (1H, m),
6.59 (1H, s), 4.68 (2H, s), 2.5
1 (3H, s). Compound 1-50: mp. 155.9 ° C 8.43 (1H, s), 8.00 (1H, s), 7.9
−7.4 (6H, m), 6.60 (1H, s), 4.8
6 (2H, s), 2.57 (3H, s) Compound 1-49: mp. 155.9 ° C 8.42 (1H, s), 8.11 (1H, dd, J =
8.2 Hz), 7.87 (1H, dd, J = 8.2H)
z), 7.80 (1H, d, J = 8 Hz), 7.6-
7.45 (2H, m), 7.33 (1H, t, J = 8H
z), 7.14 (1H, d, J = 8 Hz), 6.63
(1H, s), 5.16 (2H, s), 2.48 (3
H, s)

Compound 1-62: mp. 135.9 ° C. 8.45 (1H, s), 7.09 (1H, s), 6.6
1 (1H, s), 4.83 (2H, s), 2.64 (3
H, s), 2.54 (3H, s). Compound 1-80: oil 8.43 (1H, s), 6.59 (1H, s), 3.9
8 (2H, t, J = 7 Hz), 3.65 (2H, t, J
= 7 Hz), 3.53 (2H, q, J = 8 Hz), 2.
54 (3H, s), 1.14 (3H, t, J = 8H
z). Compound 1-81: oil 8.45 (1H, s), 6.61 (1H, s), 3.6
8 (2H, t, J = 8 Hz), 3.11 (2H, t, J
= 8 Hz), 2.55 (3H, s), 2.24 (3H,
s). Compound 1-88: mp. 71.7 ° C 8.43 (1H, s), 6.60 (1H, s), 5.9
−5.7 (1H, m), 5.3-5.05 (2H,
m), 4.05-3.9 (4H, m), 3.67 (2
H, t, J = 8 Hz), 2.54 (3H, s). Compound 1-90: mp. 87.4 ° C 8.44 (1H, s), 6.61 (1H, s), 3.6
8 (2H, t, J = 6 Hz), 3.54 (2H, t, J
= 8 Hz), 2.55 (3H, s), 2.5-2.3
(2H, m).

Compound 1-92: oil 8.42 (1H, s), 6.59 (1H, s), 3.5
0 (2H, t, J = 6 Hz), 3.47 (2H, t, J
= 6 Hz), 2.54 (3H, s), 2.21 (2H,
m). Compound 1-97: mp. 76.2 ° C 8.43 (1H, s), 6.61 (1H, s), 3.5
0 (2H, t, J = 8 Hz), 2.55 (3H, s),
2.47 (2H, t, J = 8 Hz), 2.25-2.0
5 (2H, m), 2.0-1.8 (2H, m). Compound 1-98: mp. 88.3 ° C 8.42 (1H, s), 6.60 (1H, s), 3.6
7 (3H, s), 3.45 (2H, t, J = 6 Hz),
2.54 (3H, s), 2.47 (2H, t, J = 6H
z), 2.29 (2H, m). Compound 1-103: mp. 67.7 ° C 8.43 (1H, s), 6.60 (1H, s), 3.6
1 (2H, t, J = 8 Hz), 3.42 (2H, t, J
= 8 Hz), 2.55 (3H, s), 2.2-1.8
(4H, m). Compound 1-104: mp. 69.5 ° C 8.43 (1H, s), 6.60 (1H, s), 3.6
1 (2H, t, J = 8 Hz), 3.42 (2H, t, J
= 8 Hz), 2.55 (3H, s), 2.2-1.8
(4H, m).

Compound 1-105: Oil 8.41 (1H, s), 6.58 (1H, s), 3.4
4 (2H, t, J = 5 Hz), 3.41 (2H, t, J
= 7 Hz), 3.33 (3H, s), 2.54 (3H,
s), 2.1-1.9 (2H, m), 1.85-1.6
(2H, m). Compound 1-108: 8.41 (1H, s), 7.3-
7.2 (2H, m), 7.0-6.8 (3H, m),
6.58 (1H, s), 4.01 (2H, t, J = 6H)
z), 3.46 (2H, t, J = 8 Hz), 2.53
(3H, s), 2.2-1.8 (4H, m). Compound 1-116: mp. 99.0 ° C 8.42 (1H, s), 6.60 (1H, s), 3.5
6 (2H, t, J = 6 Hz), 3.40 (2H, t, J)
= 8 Hz), 2.55 (3H, s), 2.1-1.8
(4H, m), 1.75-1.55 (2H, m). Compound 1-117: mp. 98.6 ° C 8.42 (1H, s), 6.60 (1H, s), 3.5
6 (2H, t, J = 6 Hz), 3.40 (2H, t, J)
= 8 Hz), 2.55 (3H, s), 2.05-1.8
(4H, m), 1.75-1.55 (2H, m). Compound 1-123: mp. 89.6 ° C 8.42 (1H, s), 6.60 (1H, s), 3.4
0 (2H, t, J = 9 Hz), 2.55 (3H, s),
2.40 (2H, t, J = 6 Hz), 2.05-1.9
(2H, m), 1.9-1.55 (4H, m).

Next, formulation examples are shown. Parts represent parts by weight. Formulation Example 1 Compounds 1-1 to 1-141 and 2-1 to 2-14 of the present invention
Each of 50 parts of 1, 3-1 to 3-141 and 4-1 to 4-141, 3 parts of calcium ligninsulfonate, 2 parts of sodium lauryl sulfate and 45 parts of synthetic hydrous silicon oxide were thoroughly pulverized and mixed to give each. Obtain wettable powder. Formulation Example 2 Compounds 1-1 to 1-141 and 2-1 to 2-14 of the present invention
1, 3-1 to 3-141 and 4-1 to 4-141, 25 parts each, polyoxyethylene sorbitan monooleate 3 parts, CMC 3 parts and water 69 parts were mixed, and the particle size of the active ingredient was 5 Each suspension is obtained by wet grinding to submicron size. Formulation Example 3 Compounds 1-1 to 1-141 and 2-1 to 2-14 of the present invention
1, 3-1 to 3-141 and 4-1 to 4-141, 2 parts of each, 88 parts of kaolin clay and 10 parts of talc are thoroughly pulverized and mixed to obtain each powder. Formulation Example 4 Compounds 1-1 to 1-141 and 2-1 to 2-14 of the present invention
By thoroughly mixing 20 parts of each of 1, 3-1 to 3-141 and 4-1 to 4-141, 14 parts of polyoxyethylene styrylphenyl ether, 6 parts of calcium dodecylbenzenesulfonate and 60 parts of xylene, Each emulsion is obtained. Formulation Example 5 Compounds 1-1 to 1-141, 2-1 to 2-14 of the present invention
1, 3-1 to 3-141 and 2-1 to 4-141, 2 parts each, synthetic hydrous silicon oxide 1 part, calcium ligninsulfonate 2 parts, bentonite 30 parts and kaolin clay
65 parts are pulverized and mixed well, water is added and kneaded well, and the mixture is granulated and dried to obtain each granule. Formulation Example 6 Compounds 1-1 to 1-141 and 2-1 to 2-14 of the present invention
20 parts of each of 1, 3-1 to 3-141 and 4-1 to 4-141 and 1.5 parts of sorbitan trioleate were mixed with 28.5 parts of an aqueous solution containing 2 parts of polyvinyl alcohol. After finely pulverizing with a sand grinder (with a particle size of 3 μm or less), an aqueous solution 4 containing 0.05 part of xanthan gum and 0.1 part of aluminum magnesium silicate is contained therein.
0 parts were added, and 10 parts of propylene glycol were further added and mixed by stirring to obtain a 20% suspension in water.

Next, Test Examples show that the compounds of the present invention are useful as plant disease controlling agents. In addition, this invention compound is shown by the compound number of Table 1-Table 28. The control effect of the compound of the present invention was evaluated by visually observing the area of the lesion on the test plant at the time of the investigation, and comparing the area of the lesion in the untreated section with the area of the lesion in the section treated with the compound of the present invention. did.

Test Example 1: Test for controlling rice blast (preventive effect) A plastic pot was filled with sandy loam, and rice (Nipponbare) was sowed and grown in a greenhouse for 20 days. Then, the present compound 1-1, 1-2, 1-3, 1-4, 1-5, 1-
6, 1-8, 1-9, 1-10, 1-11, 1-17,
1-18, 1-28, 1-41, 1-58, 1-68,
1-73, 1-80, 1-81, 1-88, 1-90,
1-1103, 1-104, 1-105 and 3-1 were each made into a wettable powder according to Formulation Example 1 and then diluted with water to a predetermined concentration (500 ppm), which was added to the rice leaf surface. The foliage was sprayed so as to adhere sufficiently. After spraying, air dry the plants,
A suspension of the blast fungus was spray inoculated. After the inoculation was left at 28 ° C. and in a high humidity for 6 days, the control effect was investigated. As a result, all the compounds showed that the development of blast was 30
% Or less.

Test Example 2: Test for controlling cucumber gray mold disease (preventive effect) A plastic pot was filled with sandy loam, cucumber (Sagamihanjiro) was sowed, and grown in a greenhouse for 12 days. Compounds of the present invention 1-1, 1-2, 1-3, 1-4, 1-5, 1-
6, 1-8, 1-9, 1-10, 1-11, 1-17,
1-28, 1-41, 1-58, 1-62, 1-68,
1-73, 1-81, 1-90, 1-97, 1-10
3, 1-104, 1-105, 2-1 and 3-1 were prepared as wettable powders according to Formulation Example 1, and then diluted with water to a predetermined concentration (500 ppm). The foliage was sprayed so as to sufficiently adhere to the surface. After spraying, the plants were air-dried, and a PDA medium containing a hypha of cucumber gray mold fungus was placed on the cucumber leaves. After inoculation, the plants were placed in a humid environment at 10 ° C. for 4 days, and the control effect was examined. As a result, all compounds
The development of cucumber gray mold was suppressed to 30% or less of the untreated group.

Test Example 3: Test for controlling cucumber powdery mildew (preventive effect) A plastic pot was filled with sandy loam, cucumber (Sagami Hanjiro) was sowed, and grown in a greenhouse for 12 days. Compounds of the present invention 1-1, 1-2, 1-3, 1-4, 1-5, 1-
8, 1-9, 1-10, 1-17, 1-28, 1-6
8, 1-73 and 3-1 were prepared as wettable powders according to Formulation Example 1 and then diluted with water to a predetermined concentration (500 ppm), and the foliage was sufficiently adhered to the cucumber leaf surface. Sprayed. After spraying, the plants were air-dried and spray-inoculated with spores of cucumber powdery mildew. After 11 days at 25 ° C. after the inoculation, the control effect was investigated. As a result, all compounds suppressed the onset of cucumber powdery mildew to 30% or less of the untreated plot.

Test Example 4: Wheat powdery mildew control test (therapeutic effect) Sandy loam was packed in a plastic pot, and wheat (Agriculture and Forestry 73)
No.) and sowed in a greenhouse for 10 days. Young seedlings of the wheat in which the second leaves had developed were sprinkled with wheat powdery mildew spores and inoculated. After inoculation, they were placed in a greenhouse at 23 ° C for 2 days. Compounds of the present invention 1-2, 1-3, 1-5, 1-8, 1
-9, 1-10, 1-28, 1-58, 1-68, 1-
After each of 104 and 3-1 was made into a suspension according to Formulation Example 2, it was diluted with water to a predetermined concentration (500 ppm), and sufficiently adhered to the leaves of wheat inoculated with powdery mildew. Foliage was sprayed as follows. After spraying, and after 7 days under lighting, the control effect was investigated. As a result, all compounds suppressed the occurrence of wheat powdery mildew to 30% or less of the untreated plot.

Test Example 5 Control Test for Wheat Eye Spot Disease (Preventive Effect) A plastic pot was filled with sandy loam, and wheat (Norin 73
No.) and sowed in a greenhouse for 10 days. Compounds of the present invention 1-1, 1-2, 1-3, 1-4, 1-5, 1-
6, 1-8, 1-10, 1-17, 1-18, 1-41
And 1-73 were made into an emulsion according to Formulation Example 4 and then diluted with water to a predetermined concentration (500 ppm), which was sprayed on foliage so as to sufficiently adhere to the wheat leaf surface. After spraying, the plants were air-dried and inoculated with a spore-containing PDA of wheat eye spot fungus at the root of the strain. After the inoculation, they were first placed in a dark and humid environment at 15 ° C. for 7 days, and then placed under illumination for 4 days. As a result, all the compounds suppressed the occurrence of wheat eye spot disease to 3/10 or less of the untreated plot.

Test Example 6: Wheat wilt control test (preventive effect) A plastic pot was filled with sandy loam, and wheat (agriculture and forestry 73)
No.) and sowed in a greenhouse for 10 days. Compounds of the present invention 1-2, 1-3, 1-4, 1-5, 1-6, 1-
8, 1-9, 1-10, 1-11, 1-18, 1-2
8, 1-41 and 1-58 were made into emulsions according to Formulation Example 4, then diluted with water to a predetermined concentration (500 ppm), and sprayed with foliage so as to sufficiently adhere to the wheat leaves. . After spraying, the plants were air-dried and spray-inoculated with a spore suspension of wheat wilt. After the inoculation, they were first placed in a dark and humid environment at 15 ° C. for 4 days, and then placed under illumination for 7 days. As a result, all the compounds suppressed the occurrence of wheat wilt to 30% or less of the untreated plot.

[0067]

The compound of the present invention has an excellent plant disease controlling effect.

 ──────────────────────────────────────────────────続 き Continued on the front page F term (reference) 4C050 AA01 BB05 CC08 EE03 FF02 FF03 FF05 GG01 HH02 HH03 HH04 4H011 AA01 BB09 DA02 DA15 DA16

Claims (9)

[Claims] 1. A compound represented by the general formula:[Wherein, R¹And R^TwoAre the same or different hydrogen atoms or
Represents a methyl group;^ThreeIs C3-C8 cycloalkyl
Group, an optionally substituted C1-C10 alkyl group,
Optionally substituted phenyl group, optionally substituted
Naphthyl group, monocyclic aromatic heterocyclic ring which may be substituted
Group or monocyclic non-aromatic heterocyclic group which may be substituted
Represents Where R¹Is a methyl group and R^ThreeIs replaced
Is not a phenyl group, ^TwoIs a methyl group
You. And a pyrazolopyrimidine derivative represented by the formula: 2. In the above-mentioned general formula 1, in R ³ , the optionally substituted C1-C10 alkyl group may be a halogen atom, an alkoxy group, an alkylthio group, a phenoxy group, a phenylthio group, a cyano group, An alkoxycarbonyl group, an alkylamino group, a 1-pyrrolidinyl group, a piperidino group, a morpholino group, a substituent selected from the group consisting of an allyloxy group and a propargyloxy group, and a phenyl group which may be substituted and Substituents in a good naphthyl group are a halogen atom, an alkyl group, an alkoxy group, a cyano group, a nitro group, a haloalkyl group, a haloalkoxy group, a phenoxy group, an alkylene group and an alkylenedioxy group (the alkylene group and the alkylenedioxy group Is the adjacent carbon atom on the benzene ring Substituted), wherein the substituent in the optionally substituted monocyclic aromatic heterocyclic group and the optionally substituted monocyclic non-aromatic heterocyclic group is halogen Atoms, alkyl groups,
The pyrazolopyrimidine derivative according to claim 1, which is a substituent selected from the group consisting of an alkoxy group, a cyano group, and a nitro group. 3. In the above general formula 1, R ¹ is a methyl group, R ² is a hydrogen atom, and R ³ is a substituted phenyl group or an optionally substituted naphthyl group (substituted Substituents in the phenyl group and the naphthyl group which may be substituted are a halogen atom, an alkyl group, an alkoxy group, a cyano group, a nitro group, a haloalkyl group, a haloalkoxy group, a phenoxy group, an alkylene group and an alkylenedioxy group. The pyrazolopyrimidine derivative according to claim 1, which is a substituent selected from the group consisting of: 4. In the above general formula 1, R ¹ is a hydrogen atom, R ² is a hydrogen atom or a methyl group, and R ³ is an optionally substituted phenyl group or an optionally substituted naphthyl. Group, a substituent in the optionally substituted phenyl group and the optionally substituted naphthyl group is a halogen atom, an alkyl group, an alkoxy group, a cyano group, a nitro group, a nitro group, a haloalkyl group, a haloalkoxy group, a phenoxy group, The pyrazolopyrimidine derivative according to claim 1, which is a substituent selected from the group consisting of an alkylene group and an alkylenedioxy group. 5. In the above general formula 1, R ¹ and R ² are methyl groups, and R ³ is an optionally substituted phenyl group or an optionally substituted naphthyl group; The substituent in the good phenyl group and the optionally substituted naphthyl group may be a halogen atom, an alkyl group, an alkoxy group, a cyano group, a nitro group, a haloalkyl group, a haloalkoxy group, a phenoxy group, an alkylene group and an alkylenedioxy group. The pyrazolopyrimidine derivative according to claim 1, which is a substituent selected from the group consisting of: 6. In the above general formula 1, R ³ is C3 to
C8 cycloalkyl group or optionally substituted C1
-C10 alkyl group (optionally substituted C1-C1
0 The substituent in the alkyl group is a halogen atom, an alkoxy group, an alkylthio group, a phenoxy group, a phenylthio group, a cyano group, an alkoxycarbonyl group, an alkylamino group, a 1-pyrrolidinyl group, a piperidino group, a morpholino group, an allyloxy group and a propargyloxy group. A substituent selected from the group consisting of groups. 2. The pyrazolopyrimidine derivative according to claim 1, wherein 7. In the above general formula 1, R ³ is a furyl group which may be substituted, a thienyl group which may be substituted, a pyrazolyl group which may be substituted, or a thiazolyl group which may be substituted. Or the pyrazolopyrimidine derivative according to claim 1, which is an optionally substituted pyridyl group. 8. A plant disease controlling agent comprising the pyrazolopyrimidine derivative according to any one of claims 1 to 7 as an active ingredient. 9. A compound represented by the general formula: [Wherein, R ³ has the same meaning as described above, and L represents a leaving group. And a general compound represented by the following general formula: [Wherein, R ¹ and R ² represent the same meaning as described above. And a pyrazolylamine compound represented by the following general formula: [Wherein, R ¹ , R ² and R ³ represent the same meaning as described above. ] A method for producing a pyrazolopyrimidine derivative represented by the formula: