WO1999046247A1 - Pyrazole compounds and agricultural chemicals containing the same as active ingredient - Google Patents

Abstract

Novel pyrazole compounds which are useful as an insecticide, acaricide, and bactericide. The compounds are represented by general formula (I). The agricultural chemicals are an agricultural or horticultural chemical, insecticide, acaricide, and bactericide each containing any of the compounds as the active ingredient. In said formula, R?1 and R2¿ each represents hydrogen or alkyl; Y represents a group containing ⊃C=C∫ or a group represented by -C C-; R3 represents hydrogen or a substituent, e.g., alkyl or halogeno; R4 represents hydrogen or a substituent, e.g., alkyl or acyl; R?5 and R6¿ each represents hydrogen or alkyl; and A represents phenyl or a five- or six-membered heterocyclic group.

Description

 Description Pyrazol compounds and pesticides containing them as active ingredients

Technical field

 The present invention relates to a novel pyrazole compound, and an agricultural and horticultural drug containing the pyrazole compound as an active ingredient, particularly an insecticide, acaricide, and fungicide for agricultural and horticultural use. Background art

 Conventionally, in the field of agriculture and horticulture, various fungicides and insecticides for controlling various pests have been developed and put to practical use. Therefore, conventional agricultural and horticultural fungicides and insecticides are not always satisfactory in terms of fungicidal and insecticidal effects, sterilizing and insecticide spectrum, or residual efficacy. . In addition, it could not be said that the requirements such as reduction of the number of applications and the amount of applied drugs were satisfied.

 In addition, the emergence of pathogenic bacteria and pests that have acquired resistance to conventional pesticides has also been a problem. For example, in the cultivation of vegetables, fruit trees, flowers, tea, wheat, rice, etc., various types of pesticides, for example, triazoles, imidazoles, pyrimidines, benzimidazols, dicarboximides, phenylamids Various pathogens and pests that have acquired resistance to chlorinated and organophosphorus pesticides have emerged in various places, and it is becoming increasingly difficult to control various pests caused by these pathogenic fungi and pests.

There are pesticides for which pathogens and pests have not yet acquired resistance (for example, dithiocarbamates and phthalimid pesticides), but these are generally high in the amount and frequency of application and are preferred from the viewpoint of environmental pollution. Not something. Therefore, conventional insecticides for general-purpose agricultural and horticultural useA new insecticide that shows a sufficient control effect even at low doses against various pathogens and pests that have acquired resistance to fungicides, and that has little adverse effect on the environment There is a strong need for fungicide development. Also, with regard to acaricides, the development of highly safe acaricides that exhibit excellent control and high price against mites that are resistant to conventional acaricides is expected. —On the other hand, Japanese Patent Application Laid-Open No. Hei 3—8126266 (US Pat. No. 5,039,693) or Japanese Patent Application Laid-Open No. Disclosed are substituted benzyl) pyrazolecarboxamide compounds and N- (2-substituted pyridine-5-ylmethyl) pyrazolecarboxamide compounds, which teach that the compounds have insecticidal, acaricidal and fungicidal activity. ing. However, this publication only discloses hydrogen, an alkyl group, a halogen atom, an alkoxy group, etc. as a substituent at the 4-position of the pyrazole ring, and has a double- or triple-bonded carbon-carbon unsaturated bond. There is no description about the substituent. Disclosure of the invention

 INDUSTRIAL APPLICABILITY The present invention exhibits a high control effect on various pathogens and pests that are resistant to conventional agricultural and horticultural fungicides, insecticides, and acaricides, and is an effective component of agricultural and horticultural fungicides, insecticides, and miticides The purpose is to provide useful chemical substances. Another object of the present invention is to provide a safe and effective agricultural and horticultural bactericidal, insecticidal, and acaricide active ingredient having the above characteristics and having reduced problems such as residual toxicity and environmental pollution. The purpose is to provide useful chemical substances. In particular, it is an object of the present invention to provide a 4-ethynylvirazole-5-carboxamide derivative and a vinylvirazole-5-carboxamide derivative having the above-mentioned usefulness.

 The inventors of the present invention have made intensive efforts to solve the above problems, and as a result, have found that a novel virazole compound represented by the following formula is a compound having the above characteristics, and completed the present invention. .

That is, the present invention provides a pyrazole compound represented by the following general formula (I), and a pesticide containing this compound as an active ingredient, particularly an insecticide, acaricidal, and fungicide for agricultural and horticultural use. is there.

In the formula (I), R ¹ and R ² each independently represent a hydrogen atom or an d to C ₄ alkyl group;

 Y represents a group represented by the following general formula (一般) or a group —C≡C—,

R

[In the formula (Π), R ⁷ and R ⁸ are each independently a hydrogen atom, an alkyl group of up to C ₄ , a halogen atom, an alkoxy group of up to C ₄ , an acyl group of C _{2 to} C ₇ , up to C ₇ Represents an acyloxy group. ]

R ³ is a hydrogen atom, a C, -C ₆ alkyl group, a halogen atom, a -C ₄ haloalkyl group, a C ₂ -C ₅ alkenyl group, a C ₂ -C ₅ alkynyl group, a C ₃ -C ₆ A cycloalkyl group, a hydroxyalkyl group of C, to (: 7 and a protected form thereof,

C ₅ or C ₆ hydroxycycloalkyl group, (C, to (: 4 alkylthio) d to C ₄ alkyl group, C, to C ₇ aminoalkyl group, (C, to (: ₄ alkylamino) to C ₇ alkyl group, a di (C, -C ₄ Arukiruamino) -C ₇ alkyl group, (C 1 ~ ₍₇ Ashiruamino) C, -C ₇ alkyl group, Ashiru group of C ₂ to c _7,

(C ■ to c ₆ alkoxy) carbonyl group, (c, to c ₆ alkylamino) carbonyl group, di (C, to (: 4 alkylamino) carbonyl group, carboxyl group, formyl group and protected form thereof, C ₃ to C ₉ trialkylsilyl group; or C, to C ₄ alkyl group, C, to C ₄ alkoxy group, halogen atom, nitro group, cyano group, C! To C ₄ haloalkyl group, C, to C ₄ haloalkoxy groups, Fuweniru group, full enoxy group, Ashiru group of _{C 2 ~C 7, (C,} ~C 4 alkoxy) carbonyl group, selected from the group consisting of an alkylthio group, and triflate Ruo b methylthio group -C ₄ A phenyl group which may be substituted with a substituent

R ⁴ is a hydrogen atom, an alkyl group of C! To C ₄ , an acyl group of C _{2 to} C ₇ ,

C ₄ alkoxy s xy) carbonyl group or (C, -C ₄ alkoxy) ~ (: ₄ alkyl group;

R ⁵ and R ⁶ each independently represent a hydrogen atom or an alkyl group of C, to (: ₄ ,

 A represents a group represented by the following general formulas (ma) to (! Πj). What

One FT

 (Ilia) (nib) (IIIc) (Hid) (Hie)

 (Illf) (Illg) (Illh) am) (Illj)

[In the formulas (ΠΙa) to (! Πj), R ⁹ is a hydrogen atom, (:, to ( ₈ alkyl group, to C ₄ alkoxy group, halogen atom, C _{1 to} C ₄ haloalkyl group, , a haloalkoxy group _{~C 4, C 3 ~ (:} 7 cycloalkoxy group, C, alkylthio group -C _5; or C, alkyl group -C _4, Aruke alkenyl group of C ₂ -C _5, C alkynyl group ₂ -C _5, C, alkoxy group -C _4, haloalkyl group ~ C 4, C, haloalkoxy groups -C _4, Nono androgenic atom, phenyl group, Fuwenokishi group, Shiano group, a nitro group, Formyl group and protected form thereof, hydroxy group, C ₂ -C ₇ acyl group, group represented by the following general formula (IV), (d-C ₄ alkoxy) carbonyl group, C, -C ₄ alkylthio group And a phenoxy group which may be substituted with a substituent selected from the group consisting of Properly represents the Nafuchiruokin group,

R '. Represents a hydrogen atom, C, alkyl or C, Haroaru kill groups -C ₃ of -C _6, R ′ ¹ represents a hydrogen atom, an alkyl group of CC ₄ or a paratoluenesulfonyl group. ]

OR 12

 /

 N

 Person (IV)

R ¹³

[In the formula (IV), R ¹² represents a C, to C ₄ alkyl group;

R ¹³ represents a hydrogen atom or a C ₄ alkyl group. The compound of the above general formula (I) provided by the present invention has high control activity against various pathogenic bacteria and pests which are resistant to conventional fungicides, insecticides and acaricides, and is safe. It is highly useful and is extremely useful as an agricultural and horticultural drug. BEST MODE FOR CARRYING OUT THE INVENTION

In the general formula (I), atoms and groups in the definitions of R ^{1 to} R ¹³ , A and Y will be specifically described.

R ′ and R ² are each independently a hydrogen atom or C, ~ C such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, etc. _{4 represents} a linear or branched alkyl group.

Among them, R ¹ and R ² are preferably C, to (: ₄ alkyl groups, particularly R ′ is a methyl group, and R ² is preferably a methyl group or an ethyl group.

 Y represents a group represented by the following general formula (一般) or a group —C≡C—.

XR ⁸

No, ^(π)

[In the formula (Π), R ⁷ and R ⁸ are each independently a hydrogen atom; a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, an s-butyl group, a t-group. —C ₄ to C ₄ straight or branched chain alkyl group such as butyl group; halogen atom such as fluorine atom, chlorine atom, bromine atom, iodine atom; methoxy group, ethoxy Alkoxy group, n- propoxy group, Isopurobokishi group, n- butoxy group, isobutoxy group, t-C or a butoxy group, an alkoxy group -C _4; Asechiru group, a propionyl group, n- Puchiriru group, Isopuchiriru group, n- C ₂ -C ₇ acyl groups such as valeryl group, isopallyl group, 2-methylbutyryl group, bivaloyl group, benzoyl group; etc .; C such Benzoiruokishi group, a Ashiruokishi group -C _7. ]

Y is preferably one C-C-. As R ⁷ and R ⁸ , a hydrogen atom is preferable.

R ³ is a hydrogen atom; methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, n-hexyl, etc. d to C _S straight or branched chain alkyl group; fluorine atom, chlorine atom, bromine atom, halogen atom such as iodine atom; chloromethyl group, bromomethyl group, iodomethyl group, methyl group, difluoromethyl group, trifluoromethyl group Orthomethyl group,

2-fluoroethyl group, 2-chloroethyl group, 2,2,2-trifluoroethyl group, 2,2,2-trichloroethyl group, 3-chloropropyl group, 3-bromopropyl group, 3, bromopropyl group 3,3-Trifluoropropyl, 2,2,3,3-tetrafluoropropyl, 2,2,3,3,3-pentafluoropropyl, 2,2-dichloro-1,3 , 3 —Trifluoropropyl group, 1,3 —Difluoro-2-propyl group, 1,1,1,3,3,3 —Hexafluoro-2-propyl group, 3,3,3 —Trichloropropyl propyl group, 4 one chlorobutyl group, 4, 4, 4 one Torifuruorobuchi group, 3, 3, 4, 4, 4-pen evening such Furuorobuchiru group C, Haroaru kill group -C _4; vinyl group, propene one 1- I le Group, propene 1-yl group, propene 1

3-yl group, 1-butene-1-yl group, 1-butene-2-yl group, 1-butene-3-yl group, 1-butene-4-yl group, 2-butene-1 2-yl, 2-butene-2-yl, 2-methylpropyn-1-yl, 2-methylpropyne-3-yl, 1-pentene-1-yl, 2- alkenyl C ₂ ~ C _5, such as methyl-1 one-pentene one 1 one I le group; Echiniru group, propyne - 1 Iru group, propyne - I 1-butyn-1-yl, 1-butyne-3-yl, 1-butyne-4-yl, 2-butynyl, 1-butyn-1 -yl, 3-methyl-1 - butyne 1 one I le alkynyl group of C ₂ -C _5, such as, cyclopropyl group, cyclopentyl group, a cycloalkyl group of C ₃ ~ C _6, such as a cyclohexyl group; human Dorokinmechiru group, 1 over human Dorokishechiru 1-hydroxypropan-1-yl group, 1-hydroxypropan-1-yl group, 1-hydroxypropan-1-yl group, 1-hydroxypropan-1-yl group, 2-hydroxyl group Propane 1 —yl group, 2-hydroxypropan-1-yl group, 1 —hydroxybutane 1-1 —yl group, 1 —hydroxybutane 1-2 —yl group, 1 —hydroxybutane 1-3 —y 1-hydroxybutane 4-yl group, 2-hydroxy group Sibutane-1-yl group, 2—Hydroxybutane-2-yl group, 2—Hydroxybutane-1-3-yl group, 2—Hydroxybutane-1-4-yl group, 1—Hydroxy1-2-Methylpropane-1 1 —Yl group, 1-hydroxyl-2—methylpropane-12-yl group, 1-hydroxyl-2-methylpropane-13-yl group,

2-hydroxy 1-methylpropyl group, 1-hydroxypentane-1-yl group,

1—hydroxypentane-3-yl group, 1—hydroxypentane-5-yl group,

2—hydroxypentane-2-yl group, 3—hydroxypentane-1-yl group,

3 —Hydroxypentane-3-I-yl group, 1-Hydroxy-2 —Methylbutane-1- 1-yl group, 2 —Hydroxy-1-3-methylbutane-1-2-Yyl group, 2-Hydroxyhexane 1- 2-yl group, 2-hydroxy 4-methylpentane 1-2-yl group, 2-hydroxy 3, 3-dimethylbutane 1-2-yl group, 3-hydroxy-1, 2, 4-dimethylpentane C 3, C ₇ -hydroxyalkyl groups such as 3-yl groups and the like, and those in which the hydroxyl groups of the C,-( ₇ hydroxyalkyl groups are protected, such as methyl, ethyl, n- propyl group, an isopropyl group, n- butyl group, isobutyl groups, C such as t one-butyl group, a linear or branched chain alkyl group according Arukirue one ether of -C _4; Asechiru group, a propionyl group, n- butyryl group, isobutyryl Group, n-valeryl group, isopalelli , A 2-methylbutyryl group, a vivaethyl group, a benzoyl group, and other C ₂ to (esters with a _7- amino group; a methanesulfonyl group, an ethanesulfonyl group, a benzylsulfonyl group, a Parabromoben Zensuruhoniru groups, trifluoperazine Ruo b methanesulfonyl group, trichloromethane sulfonyl group, c etc., to c ₇ sulfonic acid by a sulfonyl group ester; main Tokishimechi group, ethoxymethyl group, t-butoxymethyl group, a benzyl O carboxymethyl group Chain acetals with alkyloxyalkyl groups such as, ethoxyxetyl, etc .; cyclic acetals with tetrahydrofuranyl, tetrahydrobiranyl, 1,4-dioxane-12-yl, etc .; benzyl, parachlorobenzyl, paramethoxybenzyl by Jill group (substituted) benzyl ether; a trimethylsilyl group, Toryechirushi Lil group, triisopropylsilyl group, dimethylisopropylsilyl group, Jechiru isopropyl building silyl group, Tutorials Kirushi of C ₃ -C _9, such as a t-butyldimethylsilyl group Protected C in those selected from silyl ethers by group, the protection of human Dorokishiarukiru group -C _7; hydroxycarboxylic cyclopentane one 1-I group, hexanes one 1-I le group to inhibit de port Kishishikuro C ₅ or hydroxycarboxylic cycloalkanone kill group C ₆ and the like; methylthiomethyl group, Echiruchiomechiru group, n- propyl thio methyl group, isopropylthio methyl group, n- Petit thio methyl group, s - Petit thio methyl group, isobutyl Thiomethyl group, t-butylthiomethyl group, 1-methylthioethyl-1-yl group, 1-ethylthioethyl-1-yl group, 1-n-propylthioethyl-1-yl group, 1-isopropyl Thioethyl-1-yl, 2-methylthioethyl-1-yl, 2-ethylthioethyl-1-yl, 2-n-propylthioethyl-1-yl, 2-isopropyl 1-yl group, 1-ethylthiopropyl group, 1-ethylthiopropyl-1-yl group, 1-methylthiopyl pyr-2-yl group, 1-ethylthiopropyl _2 —Yl group, 1-methylthiopylpyr — 3-yl group, 1-ethylthiopropyl _ 3 —yl group, 2-methylthiopylpyr—1-yl group, 2 —ethylthiopropyl— 1 —Yl group, 2-methylthiopyl-pyr — 2-yl group, 2-ethylthiopropyl-12-yl group, 1-methylthiobutyl-1-yl group, 1-methylthiobutyl-2-yl Group, 1-methylthiobutyl-3-yl group, 1-methylthiobutyl-4-yl group, 2-methylthiobutyl-1-yl group, 2-methylthiobutyl-2-yl group, 2-methylthiobutyl-3 —Yl group, 2-methylthiobutyl-1- 4 —yl group, 1 —methylthio-1 2 — Chirupuropi Represented by a 1-yl group, a 1-methylthio-12-methylpropyl-12-yl group, a 1-methylthio-12-methylpropyl-13-yl group, and a 2-methylthio-12-methylpropyl group. : ₄ alkylthio) to C ₄ alkyl group; aminomethyl group, 1-aminoamino group, 2-aminoaminoethyl group, 1-aminopropane-1-yl group, 1-aminopropane-2-yl group, 1-aminopropane-1 3 —yl group, 2 —aminopropane-1 1-yl group, 2 —aminopropane-1-2 —yl group, 1 —aminobutane-1- 1 —yl group, 1 _aminobutane-12-yl group, 1 amine Nobutane-3-yl, 1-aminobutane_4-yl, 2-aminobutane1-1-yl, 2-aminobutane1-2-yl, 2-amidobutane-3-yl, 2-amido Nobutan — 4-yl group, 1 — amino-1 2 — Methylpropane-1-yl, 1-amino-2-methylpropane-2-yl, 1-amino-2-methylpropane-3-yl, 2-amino-2-methylpropyl, 1- 1-amino, 1-amino-3, 1-amino, 1-amino-5-yl, 2-aminopentane-2-yl, 3-aminopentane_1-yl, 3-Aminopentane-3-yl group, 1-Amino-2-methylbutane1-1-yl group, 2-Amino-3-methylmethylbutane-2-yl group, 2-Aminohexane-1 2-yl, 2-amino-4-methylpentane-1-yl, 2-amino-3,3-dimethylbutane-1-yl, 3-amino-1,2,4-dimethylpentane C-, C-aminoalkyl groups such as 3-yl groups, etc .; methylaminomethyl groups, ethylaminomethyl groups Group, isopropylaminomethyl group, t-butylaminomethyl group, 1-methylaminoethyl group, 1-ethylaminoethyl group, 1-isopropylaminoethyl group, 1-t-butylaminoethyl group, 2-methylaminopropane 1-2 —Yl group, 2-isopropylaminopropane-1-yl group, 2-t-butylaminopropane-1-yl group, 2-methylaminobutane-1-yl group, 2-isopropylaminobutane 1-2— 2-yl, 2-tert-butylaminobutane-1-yl, 2-methylaminopentane-1-yl, 2-ethylaminopentane-1-yl, 3-methylaminopentane-1- 3-yl, 3-isopropylaminoaminopentane-3-yl, 2-methylamino-3-methylbutane-1-yl, 2-t-butylamino-1--3-methylbutane-2-yl (C, -C ₄ alkylamino) C, such as the group, 3-methylamino-1,2,4-dimethylpentane-3-yl group, 3-isopropylamino-2,4, -dimethylpentane-3-yl group ~ (: ₇ alkyl groups; dimethylaminomethyl group, getylaminomethyl group, di-n-propylaminomethyl group, diisopropylaminomethyl group, 1-dimethylaminoethyl group, 1-getylaminoethyl group, 1- Diisopropylamino minethyl group, 2-dimethylaminopropane-12-yl group, 2-dimethylaminopropane-12-yl group, 2-dimethylaminobutane-12-yl group, 2-di-n-propylaminobutane One 2-yl group, 2-dimethylaminopenn-1-one-yl group,

2-Jethylaminopentane-1-yl group, 3-dimethylaminopentane-3-yl group, 3-diisopropylaminopentane-1-yl group, 2-dimethylamino-3—methylbutane-2- 3-yl, 3-dimethylamino-1,4-dimethylpentane 3-yl, 3-di-n-propylamino-2,4-dimethylpentane

Di (C, -C ₄ Arukiruami Roh) and 3-I le group C, ~ ₍₇ alkyl group; N- § cetyl § amino methyl, N- Puropioniruami Nomechiru group, N- n-Buchirirua Mi Nomechiru group N-isobutyrylaminomethyl group, N-bivaloylaminomethyl group, N-benzoylaminomethyl group, 1- (N-acetylamino) ethyl group, 1- (N-propionylamino) ethyl group, 1- (N-isobutyrylamino) group ) Ethyl group, 1- (N-bivaloylamino) ethyl group, 1- (N-benzoylamino) ethyl group, 2— (N-acetylamino) propane-1-yl group, 2- (N-propionylamino) G) propane-2-yl group, 2- (N-bivaloylamino) propan-2-yl group, 2- (N-benzoylamino) propane-2-yl group, 11

(N-acetylamino) butane-1-yl group, 2- (N-acetylamino) butane-2-yl group, 2- (N-propionylamino) butane-2-yl group, 2-

(N-benzoylamino) butane-2-yl group, 2- (N-acetylamino) pentane-2-yl group, 3- (N-acetylamino) pentane-3-yl group, 2-

(N-acetylamino) 1-3-methylbutane 1-2-yl group, 2- (N-acetylamino) hexane-2-yl group, 2- (N-acetylamino) 1-4-methylpentane 1-2- 2-, (N-acetylamino) 1-3,3-dimethylbutane 1 2 —Yl group, 3- (N-acetylamino) -12,4—dimethylpentane-13-yl group and other (C, ~ C ₇ ) acylamino (C, ~ C i) alkyl groups; acetyl group, Pioniru group, _n - Puchiriru group, Isopuchiriru group, n- valeryl group, Isobareri group, 2-Mechirupuchiriru group, pivaloyl group, § sills group C ₂ -C ₇ such Benzoiru group; main butoxycarbonyl group, an ethoxycarbonyl group C, to n-propoxycarbonyl, isopropoxycarbonyl, n-butoxycarbonyl, isobutoxycarbonyl, s-butoxycarbonyl, t-butoxycarbonyl, n-hexoxycarbonyl, etc. an alkoxycarbonyl group having C _6; Mechirua amino carbonyl group, E chill § amino group, n- propylamino group, an isopropyl amino Carbonyl group, n-butylaminocarbonyl group, isobutylaminocarbonyl group, s-butylaminocarbonyl group, t-butylaminocarbonyl group, n-pentylaminocarbonyl group, n-hexylaminocarbonyl group, etc. (C, to (: ₆ alkylamino) carbonyl group; dimethylaminocarbonyl group, acetylaminocarbonyl group, di-n-propylaminocarbonyl group, diisopropylaminocarbonyl group, di-n-butylaminocarbonyl group di (C ■ -C ₄ Arukiruamino) carbonyl group such as a group; a carboxyl group; or formyl group, dimethyl § Se tar derived as a protector, acyclic Asetaru such Jefferies chill § Se tar, 1, 3-Jiokisoran, Cyclic acetal such as 1,3-dioxane, 1,3-dithiolane, 1,3-dithiane, etc. Acetal groups such as thioacetal, monothioacetyl such as 1,3-oxothiolane; trimethylsilyl group, triethylsilyl group, triisopropylsilyl group, dimethylisopropylsilyl group, dimethylisopropylsilyl group, t-butyldimethylsilyl group trialkylsilyl groups such C ₃ -C ₉ the like.

R ³ includes a phenyl group which may be substituted. Examples of the substituent include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group and an s-butyl group. , linear or branched Kusaria alkyl group d ~ C ₄ of a t- butyl group and the like; main butoxy group, Etokin group, n- propoxy group, isopropoxy group, n - butoxy group, isobutoxy group, s- butoxy group, t — C '~ (^ such as butoxy group Straight or branched chain alkoxy group; fluorine atom, chlorine atom, bromine atom, halogen atom such as iodine atom, etc .; nitro group; cyano group; chloromethyl group, bromomethyl group, odomethyl group, methyl group, difluoromethyl group, Trifluoromethyl group, 2-fluoroethyl group, 2-chloroethyl group, 2,2,2-trifluoroethyl group,

2,2,2-Trichloroethyl, 3-chloropropyl, 3-bromopropyl, 3,3,3—Trifluoropropyl, 2,2,3,3-tetrafluoropropyl, 2 , 2,3,3,3-Pentafluoropropyl group, 2,2-Dichroic port-3,3,3-Trifluoropropyl group, 1,3-Difluoro-2-propyl group, 1,1,1 , 3,3,3-Hexafluoro-2-propyl group, 3,3,3-Trichloromethyl propyl group, 4-chlorobutyl group, 4,4,4-Trifluorobutyl group, 3,3,4,4 Haloalkyl group of C such as, 4-pentafluorobutyl group; difluoromethoxy group, trifluoromethoxy group, 2-fluoroethoxy group, 2-chloroethoxyquin group, 2,2,2-trifluoroethoxy group, 2 —Chloroethoxy group, 3-chloropropoxy group, 3-bromopropoxy group Group, 3, 3, 3-triflate Ruoropuropokishi group, 2, 2, 3, 3 - tetrafluoropropoxy O b propoxy group, 2, 2,

3,3,3-Pentafluoropropoxy group, 2,2-Dichloro-3,3,3-trifluoropropoxy group, 1-Trifluoromethylethoxyquin group, 1,3-Difluoro-2-propoxy 1,1,1,1,3,3,3-hexafluoro-2-propoxy, 4-chlorobutoxy, 4,4,4-trifluorobutoxy, 3,3,4,4,4-penta Fluorobutoxy group, 2,2,3,3,4,4-hexafluorobutoxy group, 2,2,3,4,4,4,1-Hexafluorobutoxy group, 2,2,3,3 , 4, 4, 4 - hepta full O Rob butoxy group, 1-triflate Ruo Russia methyl propoxy group, 1, 1, 1, 2, 2 - Pentafuruo port one 3 - C or a butoxy group, straight chain -C ₄ Or a branched-chain haloalkoxy group; a phenyl group; a phenoxy group; an acetyl group, a propionyl group, an n-butyryl group, and an n-ba Lil group, an isovaleryl group,

2-methylbutyryl group, pivaloyl group, Ashiru group of C ₂ -C ₇ such Benzoiru group; main butoxycarbonyl group, ethoxy Kin carbonyl group, n- propoxycarbonyl group, isopropoxycarbonyl group, n- butoxycarbonyl group, Isobuto Kincalbo Alkenyl group, s- butoxycarbonyl group, such as t- butoxycarbonyl group (C, -C ₄ alkoxy) carbonyl group; methylthio group, Echiruchio group, n- propylthio group, isopropylthio group, n- Puchiruchio group, Isopuchiruchio group, ~ such as s- Puchiruchio group (: linear or branched alkylthio group having _4; such triflate Ruo b methylthio group and the like, when plural substituents are present, each substituent may be the same or different The number of substituents is preferably 0 or 1.

Among them, R ³ is preferably a hydrogen atom, an alkyl group of C 1 to C ₆ or a hydroxyalkyl group of C 1 to CT, and more specifically, a methyl group and a hydroxymethyl group are most preferable. When Y is a group —C≡C—, R ³ is most preferably a hydrogen atom.

R ⁴ is a hydrogen atom; a C, C ₄ straight or branched chain such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s_butyl, t-butyl, etc. Alkyl group; acetyl group, propionyl group, n-butyryl group, n-valeryl group, isovaleryl group, 2-methylbutyryl group, bivaloyl group, benzoyl group, and other C ₂ to (: ₇ acetyl group; methoxycarbonyl group) , Ethoxycarbonyl, n-propoxycarbonyl, isopropoxycarbonyl, n-butoxycarbonyl, isobutoxycarbonyl, s-butoxycarbonyl, t-butoxycarbonyl, etc. (: ₄ alkoxy) carbonyl group; (C, -C ₄ alkoxy) C such as methoxymethyl group, ethoxymethyl group, 1-ethoxyshethyl group, t-butynemethyl group, etc. Shows -C ₄ alkyl group.

Among them, R ⁴ is preferably a hydrogen atom or a C ₂ -C, acetyl group, and more preferably, an acetyl group.

R ⁵ and R ⁶ are each independently a hydrogen atom, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, an s-butyl group, a t-butyl group, etc. ~ C _{4 represents} a linear or branched alkyl group. Among them, R ⁵ and R ⁶ are preferably a hydrogen atom or a methyl group.

A represents a group represented by the following general formulas (Ha) to (! Πj).

N

(Ilia) (Illb) (IIIc) (Hid) (Hie) -R 11

(Illf) (nig) (IHh) (Illi) (Illj) Among these, a group represented by the formula (ma) or the formula (mb) is preferable. — 1) or a group represented by the formula (ΠΙb-1) is preferable.

 (Ilia-1) (IIIb-1)

R ⁹ is a hydrogen atom; methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-amyl, isoamyl, t-amyl C, ~ (: ₈ straight or branched chain alkyl such as n-hexyl group, 1-ethyl-1-methylpropyl group, n-heptyl group, n-octyl group, 2-ethylhexyl group group; main butoxy group, Etokin group, n- propoxy group, isopropoxy opening epoxy group, n- butoxy group, isobutoxy group, s- butoxy group, t-C or a butoxy group, a -C ₄ straight or branched chain alkoxy A halogen atom such as a fluorine atom, a chlorine atom, a bromine atom and an iodine atom; a chloromethyl group, a bromomethyl group, a chloromethyl group, a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, a trifluoromethyl group, and a 2-fluoroethyl group 2, 2-chloroethyl, 2, 2, 2-trifluoroethyl, 2, 2, 2-triethyl, 3-chloropropyl, 3-bromopropyl, 3, 2-chloroethyl 3,3—Trifluoropropyl, 2,2,3,3-tetrafluoropropyl, 2,2,3,3,3-pentafluoropropyl, 2,2-dic 1,3,3,3-Trifluoropropyl, 1,3-difluoro-2-propyl, 1,1,1,3,3,3-hexafluoro-2-propyl, 3,3,3- trichloroacetic port propyl group, 4-chlorobutyl group, 4, 4, 4-Torifuruorobuchi Le group, 3, 3, 4, 4, C and 4-penta full O b butyl group, Haroaru kill group -C _4; Jifuruorome butoxy Group, trifluoromethoxy group, 2-fluoroethoxy group, 2-chloroethoxy group, 2,2,2-trifluoroethoxy group, 2-chloroethoxy group, 3-chloropropoxy group, 3-bromopropoxy group , 3,3,3-Trifluoropropoxy group, 2,2,3,3-Tetrafluoropropoxy group, 2,2,3,3,3-Pentafluoropropoxy group, 2,2-Dichloro口 一 3,3,3-Trifluoropropoxy group, 1-Trifluoro Methylethoxyquin, 1,3-difluoro-2-propoxy, 1,1,1,3,3,3-hexafluoro-2-propoxy, 4-chlorobutoxy, 4,4,4-trifluorobutoxy, 3,3,4,4,4 To pentafluorobutoxy group, To 2,2,3,3,4,4 To Xafluorobutoxy group, To 2,2,3,4,4,4_ Xafluorobutoxy, 2,2,3,3,4,4,4-heptafluorobutoxy, 1-trifluoromethylpropoxy, 1,1,1,2,2-pentafluoro-3- C 3 -C ₄ straight-chain or branched-chain haloalkoxy group such as butoxy group; C 3 -C ₇ cycloalkoxy group such as cyclopropoxy group, cyclopentyloxy group, cyclohexyloxy group, cycloheptyloxy group; methylthio group , Ethylthio, n-propylthio, isopropyl C, such as ruthio group, n-butylthio group, isobutylthio group, s-butylthio group, tert-butylthio group, n-pentylthio group, etc .: ₅ straight-chain or branched-chain alkylthio groups; It represents a good phenoxy or naphthoxy group.

 Here, the naphthyloxy group includes a mono-naphthyloxy group or a S-naphthyloxy group.

 Examples of the substituent of the phenoxy group or the naphthyloxy group include the following.

Methyl, ethyl, n-propyl, isopropyl, n-butyl, iso Butyl, s-butyl, t-butyl, etc., C, to (: ₄ linear or branched alkyl groups; or vinyl group, propene-1-yl group, propene-2-yl group , Pen-pen—3-yl, 1—butene—1—yl, 1—butene—2-yl, 1—butene—3-yl, 1—butene—4-yl, 2 —Butene— 1 —yl group, 2-butene-1-yl group, 2 —methylpropyne-1-yl group, 2-methylpropyne-3-yl group, 1 —pentene-1-yl C ₂ -C ₅ alkenyl groups such as benzyl, 2-methyl-1-pentene-1-yl, etc .; or ethynyl, propyn-1-yl, propyn-3-yl, 1-butyne _ 1 1-butyne-3-yl group, 1-butyne-4-yl group, 2-butynyl group, 1-butyn-1-yl group, 3-methyl-1-butyn-1-yl group Alkynyl group of C _{2 to} C _S such as methoxy group, ethoxy group, n_propoxy group, isopropoxy group, n-butoxy group, isobutoxy group, s-butoxy group, t-butoxy group and the like; A C ₄ straight-chain or branched-chain alkoxy group; or chloromethyl group, bromomethyl group, chloromethyl group, methyl group, difluoromethyl group, trifluoromethyl group, 2-fluoroethyl group, 2-chloroethyl 2,2,2-Trifluoroethyl, 2,2,2-Trichloroethyl, 3-chloropropyl, 3-Bromopropyl, 3,3,3-Trifluoropropyl, 2, 2,3,3-tetrafluoropropyl, 2,2,3,3,3-pentafluoropropyl, 2,2-dichloro-3,3,3-trifluoropropyl, 1,3-difluoro 2-propyl group 1,1,1,3,3,3—Hexafluoro-2-propyl, 3,3,3-Trichloromethyl propyl, 4-Chlorobutyl, 4,4,4-Trifluorobutyl, 3,3 , 4,4,4-Pentafluorobutyl and other C,-(: ₄ haloalkyl groups; or difluoromethoxy, trifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2,2 , 2—Trifluoroethoxy, 2-chloroethoxy, 3-chloropropoxy, 3-bromopropoxy, 3,3,3-trifluorochloro, 2,2,3,3-tetrafluoro Propoxy group, 2,2,3,3,3—Penthylfluoropropoxy group, 2,2-Dichloro-3,3,3—Trifluoropropoxy group, 1-Trifluoromethylethoxy group, 1,3 —Difluoro-2— Propoxy, 1,1,1,3,3,3-hexafluoro-2-propoxy, 4-chlorobutoxy, 4,4,4-trifluorobutyne, 3,3,4,4,4-penta Fluorobutoxy group, 2,2,3,3,4,4—Hexafluorobutoxy group, 2,2,3,4,4,4—Hexafluorobutoxy group, 2,2,3,3 , 4, 4, 4 - hepta full O Rob butoxy group, 1 one triflumizole Ruo b methylpropoxy group, 1, 1, 1, 2, 2 - Pentafuruo port one 3 - linear C, -C ₄ or butoxy group Or a branched-chain haloalkoxy group; or a halogen atom such as a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom; or a phenyl group; or a phenoxy group; or a cyano group; or a nitro group; Dimethylaceta, which is induced as a formyl group and its protective form , Acyclic acetal such as acetyl ether, 1,3-dioxolane, cyclic acetal such as 1,3-dioxane, 1,3-dithiolane, dithioacetal such as 1,3-dithiane, 1, 3-acetals such as monothioacetals such as oxothiolane; or hydroxy groups; or hydroxy groups; or acetyl groups, propionyl groups, n-butyryl groups, n-valeryl groups, isovaleryl groups, 2- A C ₂ -C ₇ acyl group such as a methylbutyryl group, a bivaloyl group and a benzoyl group; or an oxime group represented by the following general formula (W);

OR ¹²

 N

 ji (IV)

r ₁₃

[In the formula (IV), R ¹² represents C, to (: ₄₎ such as methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, s-butyl group and t-butyl group. R ¹³ represents a hydrogen atom or a methyl, ethyl, n-propyl, isopropyl or n-butyl group. group, isobutyl group, s - butyl groups, C such as t one-butyl group, a straight or branched chain alkyl group having -C ₄ is a methyl group was a hydrogen atom or among these the most preferred..

Or methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, isopropoxycarbonyl, n-butoxycarbonyl, isobutoxy Such as a cicarbonyl group, S-butoxycarbonyl group and t-butoxycarbonyl group

(C, -C ₄ alkoxy) carbonyl group; or C, -C ₄ straight chain such as methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, isobutylthio, s-butylthio, etc. Or a branched-chain alkylthio group; or a trifluoromethylthio group.

When there are a plurality of substituents in the phenoxy group or naphthyloxy group for R ⁹ , the respective substituents may be the same or different. The number of substitution groups is preferably one or two.

Examples of the substituent of the phenoxy group or the naphthyloxy group include the halogen atoms described above, d to C ₄ linear or branched alkyl groups, C, to C ₄ haloalkyl groups, and C, to C ₄ linear or branched chains. Alkylthio groups, C ₂ to (: ₅ alkynyl groups, oxime groups represented by the general formula (W), and C, to C ₄ linear or branched alkoxy groups are preferred.

R ⁹ is preferably an optionally substituted phenoxy group or a naphthylquine group, and more preferably a substituent of the group represented by the above formula (ma-1) or (mb-1). . R ⁹ is most preferably a phenoxy group substituted by a halogen atom.

When A is a group represented by the formula (mi), R '° is a hydrogen atom; methyl, ethyl, n-propyl, isopropyl, η-butyl, isobutyl, s-butyl, a C ₆ to C ₆ linear or branched alkyl group such as t-butyl group, n-amyl group, isoamyl group, t-amyl group, n-hexyl group, 1-ethyl-1-methylpropyl group; fluoromethyl group , Chloromethyl, bromomethyl, difluoromethyl, dichloromethyl, dibromomethyl, trifluoromethyl, trifluoromethyl, tribromomethyl, pentafluoroethyl, heptafluoropropyl, etc. C _{3 represents a} haloalkyl group.

When A is a group represented by the formula (mj), R ¹¹ is a hydrogen atom; methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, C of a t- butyl group and the like, -C ₄ alkyl group; p-toluenesulfonyl Represents a group.

 Groups not specifically shown in the above groups are selected in any combination from the above atoms and groups, or in accordance with generally known common sense.

 In the above formula (I), when the compound has a carboxyl group or an amino group, a salt thereof is also included in the compound of the present invention. Examples of the salt include commonly used agricultural and horticulturally acceptable salts known per se. Further, isomers of the compound represented by the above general formula (I) are also included in the compounds of the present invention.

 Preferred examples of the pyrazole compound represented by the general formula (I) include a compound represented by the following general formula (I-11).

⁵ , R ⁶ and R ⁹ are the same as defined in the general formula (I), and W is a group CH or a nitrogen atom.

In the general formula (I-11), preferred examples of the atoms and groups in the definitions of R ′ to R ⁶ and R ⁹ include the same as those defined in the general formula (I).

Furthermore, as particularly preferred compounds represented by the above general formula (I-11), R ¹ and R ² are each independently an alkyl group of d to C ₄ , and R ³ , R \ R ⁵ and R ⁶ is a hydrogen atom at the same time, W is a group CH or a nitrogen atom, R ⁹ is a halogen atom, a C, -C ₄ alkyl group, a C, -C ₄ haloalkyl group, a C, -C ₄ alkylthio group , An alkynyl group of C ₂ to C ₅ , an oxime group represented by the general formula (W), and a phenyl or naphthyloxy group which may be substituted with a substituent selected from the group consisting of an alkoxy group of C, to (: 4) The compound is a group.

—The compounds of the present invention represented by the general formula (I) include Hasmonyo tow, Konaga, and Tyano Lepidoptera, such as Kamakumamakimaki, Kobumemeiga, and Futaba suzuki; Dermophytes, such as Tobi-iro-jin-koku, Shiro-Gonbuka, etc., Leaf-hoppers, such as Lepidoptera, Tyanomy. Hemiptera, such as stink bugs such as blue stink bugs, Coleoptera, such as Lepidoptera, Chrysomelidae, Leaf beetles, and Azukizomushi; Diptera, such as house flies and Akajeka; It has a high control activity against eggs and larvae of the order Acarina, such as Citrus red mites, Citrus unicinus, and Cyanophoridae, and is therefore useful as an active ingredient for agricultural and horticultural insecticides and danicidal agents. Further, the compound of the present invention has a high bactericidal effect against phytopathogenic fungi such as blast fungus, rust fungus and downy mildew fungus, and is useful as an active ingredient of a fungicide for agricultural and horticultural use. However, insects, mites, phytopathogenic fungi and the like to be controlled by the compounds of the present invention are not limited to those exemplified above. When the compound of the present invention represented by the general formula (I) is used as an insecticide, acaricide, or fungicide for agricultural and horticultural use, it may be used alone, but it may be used alone. Preferably, it is in the form of a composition produced with the aid of an auxiliary. In other words, it is preferable to use emulsions, wettable powders, powders, flowables, fine granules, granules, tablets, oils, sprays, aerosols, etc., but conventional pesticides for agricultural and horticultural use The form of the acaricide or fungicide is not limited. Further, one or more of the above compounds may be blended as an active ingredient.

 The pesticide adjuvants used for producing the above-mentioned agricultural and horticultural insecticides, acaricides, and fungicides include, for example, improving, stabilizing, and dispersing the effects of agricultural and horticultural insecticides, acaricides, and fungicides. It can be used for the purpose of improving the properties. Specific examples include a carrier (diluent), an emulsifier, a spreading agent, a wetting agent, a dispersant, and a disintegrant.

Examples of the liquid carrier include water, aromatic hydrocarbons such as toluene and xylene, alcohols such as methanol, butanol and glycol, ketones such as acetone, amides such as dimethylformamide, and sulfoxides such as dimethyl sulfoxide. , Methylnaphthalene, cyclohexane, animal and vegetable oils, fatty acids and the like. Solid carriers include clay, kaolin, talc, diatomaceous earth, silica, calcium carbonate, Montmorite mouth, feldspar, quartz, alumina, sawdust, nitrocellulose, starch, gum arabic and the like can be used.

 Usable surfactants can be used as emulsifiers and dispersants, for example, higher alcohol sodium sulfate, stearyltrimethylammonium chloride, polyoxyethylene alkylphenyl ether, lauryl betaine, etc. Anionic surfactants, cationic surfactants, nonionic surfactants, amphoteric surfactants and the like can be used. A spreading agent such as polyoxyethylene nonylphenyl ether and polyoxyethylene lauryl phenyl ether; a wetting agent such as dialkyl sulfosuccinate; a fixing agent such as carboxymethyl cellulose and polyvinyl alcohol; lignin sulfone Disintegrants such as sodium citrate and sodium lauryl sulfate can be used.

 The content of the active ingredient in the agricultural and horticultural insecticide, acaricide, and fungicide of the present invention is as follows.

The amount is selected from the range of 0.1 to 99.5% by weight, and may be appropriately determined depending on various conditions such as the form of the preparation and the method of application. For example, about 0.5 to 20% by weight of the powder is preferable. It is preferably about 1 to 10% by weight, about 1 to 90% by weight for a wettable powder, preferably about 10 to 80% by weight, and about 1 to 90% by weight for an emulsion, preferably about 10 to 4% by weight. It is preferred to produce such that they contain 0% by weight of active ingredient.

For example, in the case of an emulsion, an emulsion can be prepared by appropriately mixing a solvent, a surfactant and the like with the compound of the present invention as an active ingredient. May be applied after dilution. In the case of wettable powders, the above compound of the active ingredient, the solid carrier, and a surfactant are mixed to produce a wettable powder, and the hydrated liquid is diluted with water to a predetermined concentration before use, and then applied. Is also good. In the case of powder, an auxiliary such as a solid carrier may be added to the above compound as an active ingredient, if necessary, and the mixture may be used as it is. In the case of granules, the granules may be produced by mixing the above-mentioned compound as an active ingredient, a solid carrier, a surfactant and the like and granulating the granules, and may be applied as it is. In any case, the production method of each of the above-mentioned preparation forms is not limited to the above-mentioned one, and can be appropriately selected by those skilled in the art according to the kind of the active ingredient, the purpose of application, and the like. The agricultural and horticultural insecticides, acaricides, and fungicides of the present invention include, in addition to the compound of the present invention, an active ingredient, other fungicides, insecticides, acaricides, herbicides, and insect growth regulators. Any active ingredient such as fertilizer, soil conditioner, etc. may be added. The method for applying the fungicide for agricultural and horticultural use, the insecticide and the acaricide of the present invention is not particularly limited, and it may be applied by any method such as foliage application, water application, soil treatment, seed treatment, and soil admixture treatment. You can do this. For example, in the case of foliar application, a solution having a concentration range of 5 to 100 ppm, preferably 10 to 500 ppm is applied at a rate of about 100 to 200 liters per 10 ares. It can be used in dosages. For surface applications, the application rate is usually 1 to 10 kg per 10 ares for granules with 5 to 15% of active ingredient. For soil treatment, it can be used in. 5 to 1 0 0 0 p pm concentration range of the solution to 1 m ² per 1 to 1 0 rates Torr about facilities doses. In the case of seed treatment, a solution in a concentration range of 10 to 100 ppm per 1 kg of seed weight can be applied to the solution in an amount of about 10 to 100 milliliters.

 The compound of the present invention represented by the general formula (I) can be produced, for example, according to the following reaction formula.

Wherein R ′, R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , Y and A are as defined in the general formula (I), and Q is a halogen atom such as a chlorine atom, a bromine atom, etc. A hydroxyl group; an alkoxy group such as a methoxy group, an ethoxy group, and a propoxy group; ]

In the general formula (V), when Q is a halogen atom, as a solvent, an aromatic hydrocarbon such as benzene, toluene or xylene; a ketone such as acetone, methyl ethyl ketone or methyl isobutyl ketone; Halo such as methylene chloride Genated hydrocarbons; water; esters such as methyl acetate or ethyl acetate; polar compounds such as tetrahydrofuran (THF), acetonitrile, dioxane, N, N-dimethylformamide, N-methylpyrrolidone (NMP) or dimethylsulfoxide The compound represented by the general formula (I) can be obtained by reacting the compound represented by the general formula (VI) with a solvent in the presence of a base at 0 to 30 ° C, preferably 0 to 5 ° C. Examples of the base include sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, pyridine and triethylamine.

 In the case where Q is a hydroxyl group or an alkoxy group in the general formula (V), the solvent may be used in a solvent-free state or in a high boiling point solvent such as N, N-dimethylformamide, N-methylpyrrolidone or dimethylsulfoxide. The compound of the general formula (VI) can be obtained by reacting the compound of the general formula (VI) with the compound preferably at 200 to 250. In particular, when Q is a hydroxyl group in the general formula (V), the compound represented by the general formulas (V) and (V) in a polar solvent as described above at −10 to 80 ° C., preferably 0 to 50 ° C. Compounds represented by the general formula (VI) include dicyclohexylcarbodiimide (DCC), diisopropylpropylcarbodiimide (DIPC), N-ethyl-N'-3-dimethylaminopropylcarbodiimide (WS CI), benzotriazo-l-l-lu-tris (dimethylamino) phosphoniumhexafluorophosphoride (BOT), diphenylphosphoryl azide (DPPA), etc. [In some cases, N-hydroxysuccinimide (HONS u), 1-hydroxybenzotriazole (HOB t), 3-hydroxy-14-oxo-3,4-dihydroxy-1,2,3-benzotriazine (HOOB t), etc. ] Or carbonyldiimidazole CD I) and the like to give compounds of general formula (I) by reacting a.

The compound represented by the general formula (V) is represented by the method described in, for example, Anna 1 ender Chemie, Justus Liebig's, 536, 97 (1938), and represented by the general formula (VI). Such a compound can be produced, for example, according to the method described in Journa 1 fur Practische Chemie, 146, 95 (1936). Further, when Y is a group —c≡c—, it can be produced, for example, according to the following reaction formula.

 (VII) (I-a)

[Wherein, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ and A are as defined in the general formula (I). ]

 That is, a compound of the general formula (W) in which X is a halogen such as a chlorine atom, a bromine atom or an iodine atom is synthesized according to a known synthesis method as described above, and an aromatic solvent such as benzene, toluene or xylene is used as a solvent. Hydrocarbons; halogenated hydrocarbons such as chloroform and methylene chloride; water; esters such as methyl acetate and ethyl acetate; tetrahydrofuran, 1,2-dimethoxetane, acetonitrile, dioxane, N, N-dimethylformamid Or a polar solvent such as N-methylpyrrolidone or dimethylsulfoxide, or a mixed solvent thereof in the presence of an amine such as getylamine, butylamine, and triethylamine, or a base of an inorganic salt such as carbonate lime. Or 0-150 in amines such as getylamine, triethylamine, etc. The compound (M) and the terminal acetylene compound (<<) are combined with 0.1 to 10 Omo 1%, preferably 1 to 2 Omo 1% tetraxtriphenylphenylphosphine palladium.

(0), dichloroditriphenylphosphine palladium (Π), diacetoxyditriphenylphosphinepalladium (Π), or a palladium catalyst such as palladium carbon, and 1 to 10 Omo 1%, preferably 1 to 2 Omo 1 % Copper iodide

The compound of the formula (I-a) can also be produced by the reaction using (1) and the like. When Y is a group HC = CH—, for example, it can be produced according to the following reaction formula.

(G a) (I-b)

[Wherein, R ′, R ² , R ³ , R ⁴ , R ⁵ , R ⁶ and A are as defined in the general formula (I). ]

That is, as described above, a compound represented by the general formula (Ia) synthesized according to a known synthesis method is used, and a solvent is a hydrocarbon such as hexane, heptane or cyclohexane; or an aromatic such as benzene, toluene or xylene. Hydrocarbons; esters such as methyl acetate and ethyl acetate; polar solvents such as tetrahydrofuran, 1,2-dimethoxetane, acetonitrile, dioxane, N, N-dimethylformamide, or N-methylpyrrolidone , and using a mixed solvent thereof, [added quinoline sometimes] 1 to 1 0 0 wt%, preferably 1 to 2 0% by weight of Rindora first catalyst and P d-B a S 0 by _4, It can also be produced by performing a partial contact reduction reaction of a triple bond site at 5 to 50 ° C. in a hydrogen atmosphere at 1 to 10 atm. Example

 Hereinafter, the present invention will be described more specifically with reference to examples, but the present invention is not limited to the following examples.

 <Example 1>

 Preparation of 4-ethynyl-l, 3-dimethyl-lN- [2- (2-naphthoxy) pyridin-5-ylmethyl] -pyrazole-5-carboxamide (Compound No. 01)

4-Ethynyl-1,3-dimethyl-pyrazole-5-carboxylic acid (2.36 g, 14.4 mmo 1) was added to toluene (10 m 1) and thionyl chloride (6.00 g, 50. 4 mmo 1), heat and reflux for 1.5 hours, and then Then, toluene and excess thionyl chloride were distilled off to obtain a crude acid chloride.

 2- (2-Naphthoxy) -1-5-methylmethylpyridine (3.75 g, 15.0 mmo 1) combined with ethyl acetate (30 m 1) and triethylamine (3.03 g, 30.0) mmo 1) was added, and a solution of crude acid chloride in ethyl acetate (20 ml) was gradually added dropwise while cooling with ice-cold water. After completion of the dropwise addition, the mixture was stirred at room temperature for 30 minutes. The reaction was stopped by adding water, and ethyl acetate was further added to separate the organic layer. The organic layer was washed with 1N aqueous sodium hydroxide solution, 1N hydrochloric acid and saturated saline, dried over anhydrous sodium sulfate, and filtered. The solvent was distilled off to obtain a crude product. By purifying this with a silica gel column (silica gel 200 g, hexane: ethyl acetate = 1: 1 -2: 3), 4-ethynyl-1,3-dimethyl-N— [2- (2- (Naphthoxy) pyridine-5-ylmethyl] monopyrazole-5-carboxamide (Compound No.001) (0.87 g, yield 15%) was obtained. Below is the 'H-NMR data and melting point ¾gc

_{Ή-NMR (CD C 1 3} ): 2. 3 0 (s, 3 H), 3. 4 9 (s, 1 Η), 4. 1 6 (s, 3 Η), 4. 5 9 (d, 2Η), 6.966 (d, 1Η), 7.29 (dd, 1Η), 7.41-7.51 (m, 2Η), 7.56 (d, 1 Η), 7.58 (br, 1Η), 7.72-7.89 (m, 4Η), 8.19 (d, 1Η)

 mp: 1 3 9—140 ° C

 <Example 2>

 Production of 4-ethynyl-1,3-dimethyl-N- [2- (3_trifluoromethylphenoxy) pyridine-15-ylmethyl] -pyrazole-15-carboxamide (Compound No.05)

4- (ethynyl) -1,3-dimethyl-pyrazole-5-carboxylic acid (0.50 g, 3.05 mmo 1) was added with THF (6 ml) and NMP (lml). Nilzymidazole (0.69 g, 4.29 mmo 1) was added. After stirring at room temperature for 3 hours, THF (5 m 1) of 2- (3-trifluoromethylphenokine) -5-aminomethylpyridine (0.82 g, 3.05 mmo 1) was added, and 3 0 The mixture was subjected to a minute reaction, water and ethyl acetate were added, and the organic layer was separated. The organic layer was washed with saturated saline, dried over anhydrous sodium sulfate, filtered, and the solvent was distilled off to obtain a crude product. By purifying this with a silica gel column (silica gel 30 g, hexane: ethyl acetate = 3: 2), 4-ethynyl-1,3-dimethyl-1-N— [2-

(3-trifluorophenoxy) pyridin-5-ylmethyl] monopyrazole-15-carboxamide (Compound No. 05) (0.72 g, yield 57%) was obtained. The 'H-NMR data and melting point are described below.

_{Ή-NMR (CD C 1 3} ): 2. 3 1 (s, 3 H), 3. 5 0 (s, 1 H), 4. 1 6 (s, 3 Η), 4. 5 9 (d, 2Η), 6.97 (d, 1Η), 7.33 (m, 1Η), 7.40 (m, 1Η), 7.44-7.54 (m, 2 2) Η), 7.60 (br, 1Η), 7.76 (dd, 1Η), 8.17 (d, 1Η) mp: 1 16 ° C

 Example 3>

 3-Ethyl-1-methyl-N— [2- (2-naphthoxy) pyridine-15-ylmethyl] -14-trimethylsilylethynylvirazole-5-carboxamide (αα 0 7) Manufacturing of

3-Ethyl-1- 4-methyl-1-methyl-2- [2- (2-naphthoxy) pyridin-5-ylmethyl] Pyrazol-5-carboxamide (3.00 g, 5.86 mmo 1 )) And triethylamine (100 ml), and tetrakis (triphenylphosphine) palladium (0) (0.14 g, 0.12 mmol), cuprous iodide (0.08 g, 0.08 g). 4 2 mmo 1) was added. Here, trimethylsilylacetylene (2.88 g, 29.3 mmo 1) was added dropwise, and a reaction was performed for 2 hours under reflux with heating. The precipitated salts were filtered, the filtrate was concentrated, ethyl acetate was added, and the organic layer was washed with 1N hydrochloric acid, water, saturated aqueous sodium hydrogen carbonate, and saturated saline in this order, dried over anhydrous sodium sulfate, filtered, and the solvent was removed. Was distilled off to obtain a crude product. This was purified by a silica gel column (silica gel: 120 g, hexane: ethyl acetate = 2: 1), followed by recrystallization from hexane to give 3-ethyl-11-methyl-N— [2- (2- Naphthoxy) pyridin-5-ylmethyl] -14-trimethylsilylethynylpyrazole-5- Carboxamide (compound {α} 07) (2.26 g, 80% yield) was obtained. The following shows the 'H-NMR data and melting point.

_{Ή-NMR (CD C 1 3} ): 0. 1 5 (s, 9 H), 1. 2 6 (t, 3 H), 2. 6 8 (q, 2 Η), 4. 1 7 (s, 3Η), 4.58 (d, 2 ，), 6.9

6 (d, 1Η), 7.27 (d d, 1Η), 7.44 (d d d, 1Η), 7.4

7 (d d d, 1Η), 7.55 (d, 1Η), 7.73-7.89 (m, 5Η), 8.19 (d, 1Η)

 m ρ: 8 3-8 4 ° C

 <Example 4>

 1,3-Dimethyl Ν— [4- (4-tritoloxy) benzyl] production of 1,4-vinylpyrazol-5-carboxamide (Compound No. 34)

4-Ethinyl 1,3-dimethyl-1-N— [4- (4-triloquine) benzyl] -pyrazol-1-5-carboxamide (0.70 g, 1.95 mmol) was added to toluene ( The mixture was dissolved in 20 m 1), added with a catalyst (0.07 g), and subjected to a catalytic reduction reaction in a hydrogen atmosphere at room temperature for 20 minutes. After filtering off the catalyst, the product was concentrated under reduced pressure to obtain a constituent product, which was purified on a silica gel column (silica gel 20 g, hexane: ethyl acetate = 3: 2) to give 1,3- Dimethyl-N- [4- (4-tolyloxy) benzyl] -14-vinylbiazol-5-carboxamide (Compound No. 34) (0.43 g, 61% yield) was obtained. The ¹ H-NMR data and melting point are described below.

 H-NMR (CDC ") 2.26 (s, 3 H), 2.34 (s, 3 H),

402 (s, 3H), 4.55 (d, 2H), 5.35 (dd, 1H), 54 (dd, 1H), 6.28 (br, 1 H), 6.57 (dd, 1 H), 691 (dd, 2 H), 6.95 (dd, 2 H) 7.14 (dd, 2 H), 7 26 (dd , 2 H)

 m p: 104 to 106 ° C

The compounds described in Table 11 were synthesized according to the methods described in Examples 1 to 4 above.

 Table 1 (continued)

Compound No R ¹ R ² YR ³ R ⁴ R ⁵ R ⁶

 H

047 CH _{3 2} x ₅ HHH

H

048 CH ₃ C ₂ H ₅ HHH

H

049 CH ₃ C ₂ H ₅ HHH

H

_{050 CH 3 C 2 H 5 HHH} x 0 r sc¾

The following shows the Η-NMR data and melting points of the compounds shown in Table 11 above. <Compound No. 02>

_{Ή-NMR (CDC 1 3)} :. 0. 1 5 (s, 9 H), 2. 2 9 (s, 3 H), 1 7 (s, 3 H), 4. 5 8 (d, 2 H ), 6.96 (d, 1Η), 7.2 (dd, 1H), 7.27-7.38 (m, 2Η), 7.55 (d, 1Η), . 7 6 (dd, 2 H), 7.80 (br, 1 Η), 7.86 (dd, 2 Η),. 18 (d, 1 H)

 m p: 108-110 ° C

<Compound Na003>

 'H-NMR (CD C 13): 2.03 (s, 3Η), 3.50 (s, 1Η), .16 (s, 3H), 4.60 (d, 2 H), 6.98 (bt, 1H), 7.3 (d, 2H), 7.61 (br, 1H), 7.65 (d, 2H), 7.77 (dd, 1 H), 8.18 (d, 1 H)

 mp: 1 4 9—15 0 ° C

<Compound Na004>

'H-NMR (CD C 1 3):. 0. 1 5 (s, 9 H), 2. 2 9 (s, 3 H), 1 7 (s, 3 H), 4. 5 9 (d, 2H), 6.99 (bt, 1H), 7.2 (d, 2H), 7.65 (d, 2H), 7.77 (dd, 1H), 7.8 4 (bt, 1 H), 8.0 3 (d, 1 H)

 mp: 1 18.0-1 18.4 ° C

Compound Na 0 6>

_{Ή-NMR (CDC 1 3)} :. 1. 2 6 (t, 3 H), 2. 7 0 (q, 2 H), 4 9 (s, 1 H), 4. 1 3 (s, 3 H ), .59 (d, 2 H), 6.9 (d, 1 H), 7.28 (dd, 1 H), 7.43 (ddd, 1 H), 7.4 (ddd, 1H), 7.56 (d, 1H), 7.60 (br, 1H), 7.7 (dd, 1H), 7.78 (dd, 1H), 7.8 5 (dd, 1 H), 7.8 (d, 1 H), 8.19 (d, 1 H)

mp: 1 18 ° C <Compound No. 08>

_{Ή-NMR (CD C 1 3} ): 1. 0 0 (t, 3 H), 1. 2 5 (t, 3 H), 1. 4 2 (s, 3 H), 1. 6 6 (s, 1H), 1.69 (m, 2H), 2.66 (q, 2H), 4.16 (s, 3H), 4.57 (d, 2H), 6. 9 5 (d, 1 H), 7.27 (dd, 1 H), 7.44 (ddd, 1 H), 7.47 (ddd, 1 H), 7.54 (d, 1 H), 7.63 (br, 1H), 7.73-7.

8 9 (m, 4 H), 8.2 1 (d, 1 H)

 mp: 1 0 8—1 1 0. C

 <Compound N 0 9>

_{Ή-NMR (CDC 1 3)} : 1. 3 1 (t, 3 H), 2. 7 5 (q, 2 H), 4. 2 0 (s, 3 H), 4. 6 0 (d, 2 H), 6.83 (d, 1H), 7.1

9—7.35 (m, 5H), 7.44 (ddd, 1H), 7.48 (ddd, 1H), 7.53 (d, 1H), 7.66 (br, 1 H), 7.7 1-7.88

(m, 4 H), 8. 19 (d, 1 H)

 mp: 9 7 ° C

 <Compound No. 0 10>

 'H-NMR (CDC "): 1.24 (t, 3 H), 2.35 (br, 1 H), 2.66 (q, 2 H), 4.14 (s, 3 H), 4.36 (d, 2H), 4.59 (d, 2H), 6.96 (d, 1H), 7.27 (dd, 1H), 7.4 2-7.55 (m, 4 H), 7.73-7.89 (m, 4 H), 8.26 (d, 1 H) mp: 1 2 1-1 2 2 ° C

 <Compound No. 0 1 1>

Ή-NMR (CD C 13): 1.23 (t, 3 H), 1.82 (3, 3 H), 2.64 (q, 2 H), 4.09 (d, 2 H), 4.14 (s, 3H), 4.65 (d, 2H), 6.09 (br, 1H), 6.96 (d, 1H), 7.2 7 (dd, 1 H), 7.44 (ddd, 1 H), 7.47 (ddd, 1 H), 7.54 (d, 1 H), 7.75-7.88 (m, 5 H), 8.30 (d, 1 H) mp: 1 46-1 49 ° C <Compound No. 0 1 2>

 Ή-NMR (CDC 13): 1.24 (t, 3 H), 1.39 (d, 3 H),

2.36 (br, 1H), 2.65 (q, 2H) 4.15 (s, 3H), 4.

5 8 (d, 2 H), 4.64 (p, 1 H), 6.96 (d, 1 H), 7.27 (dd, 1 H), 7.44 (ddd, 1 H), 7.48 (ddd, 1 H), 7.

55 (d, 1H), 7.56 (br, 1H), 7.73-7.89 (m, 4H) 8.24 (d, 1H)

 m p: 8 5-8 8 ° C

 Compound NQ.0 1 3>

 Ή-NMR (CDC "): 1.25 (t 3 H), 1.45-1.72 (m,

6H), 2.68 (q, 2H), 3.45-3.53 (m, 1H), 3.76—3.85 (m, 1H), 4.1 6 (s, 3H), 4.42 (s, 2H), 4.5

8 (d, 2 H), 4.78 (t, 1 H), 6.98 (d, 1 H), 7.28 (dd, 1 H), 7.43 (ddd, 1 H) ), 7.47 (ddd, 1 H), 7.55

(d, 1 H), 7.72-7.88 (m, 5 H), 8.20 (d, 1 H) mp: 65-66 ° C

 <Compound No. 0 1 4>

_{Ή-NMR (CD C 1 3} ): 1. 2 0 (t, 3 H), 1. 2 6 (t, 3 H) 2. 6 8 (q, 2 H), 3. 5 1 - 3. 7 5 (m, 4 H) 4.16 (s, 3 H), 4.56 (d, 2 H), 5.39 (s, 1 H), 6.95 (d, 1 H)

7.28 (dd, 2 H), 7.43 (ddd, 1 H), 7.47 (ddd, 1 H), 7.55 (d, 1 H), 7.63 (br , 1 H), 7.75-7.88

(m, 4 H), 8.20 (d, 1 H)

 m p: 8 8-9 1 ° C

 <Compound No. 0 15>

'H-NMR (CD C 1 3): 1. 2 9 (t, 3 H), 2. 7 4 (q, 2 H), 4. 1 7 (s, 3 H), 4. 6 0 (d , 2 H), 6.99 (d, 1 H), 7.2

9 (br, 1H), 7.29 (dd, 2H), 7.43 (ddd, 1H), 7 4 7 (ddd, 1 H), 7.57 (d, 1 H), 7.76-7.89 (m, 4 H), 8.22 (d, 1 H), 9.3 0 (s, 1 H)

 mp: 1 4 1-1 42 ° C

 <Compound No. 0 16>

_{Ή-NMR (CDC 1 3)} : 1. 2 5 (t, 3 H), 2. 6 6 (q, 2 H),

4.16 (s, 3H), 4.31 (s, 2H), 4.58 (d, 2H), 6.9

7 (d, 1 H), 7.28 (dd, 2 H), 7.43 (dd d, 1 H), 7.4

8 (d d d, 1 H), 7.56 (d, 1 H), 7.76-7.89 (m, 4 H) 8.2 1 (d, 1 H)

 m p: 109-110 ° C

 Compound No. 0 1 7>

_{Ή-NMR (CD C 1 3} ): 1. 2 5 (t, 3 H), 2. 0 5 (s, 3 H),

2.67 (q, 2H), 4.16 (s, 3H), 4.63 (d, 2H), 4.7

9 (s, 2H), 6.93 (d, 1H), 728 (dd, 2H), 7.43

(ddd, 1 H), 7.46 (ddd, 1 H), 7.54 (d, 1 H), 7.74—7.87 (m, 5 H), 8.2 1 ( d, 1 H)

 (Viscous oil)

 <Compound No. 0 18>

_{Ή-NMR (CD C 1 3} ): 1. 2 6 (t, 3 H), 2. 7 0 (q, 2 H),

3.50 (s, 1H), 4.16 (s, 3H), 4.60 (d, 2H), 6.97 (d, 1H), 7.33 (d , 1 H), 7.40 (br, 1 H), 7.44—7.54 (m, 2 H), 7.62 (br, 1 H), 7.77 (dd, 1 H),

8.1 7 (d, 1 H)

 m p: 80-82 ° C

 <Compound Na 0 1 9>

'H - NMR (CD C 1 3): 1. 2 6 (t, 3 H), 2. 7 0 (q, 2 H), 3. 4 9 (s, 1 H), 4. 1 6 (s , 3H), 4.58 (d, 2H), 6.92 (d, 1H), 7.07 (dd, 2H), 7.35 (dd, 2H), 7 . 5 9 (br, 1H), 7.72 (dd, 1H), 8.11 (d, 1H)

 mp: 1 3 5-1 3 8 ° C

<Compound No. 0 20>

_{■ H-NMR (CDC 1 3} ):. 0. 1 4 (s, 9 H), 1. 2 6 (t, 3 H), 6 5 (q, 2 H), 4. 1 7 (s, 1 H) 4.56 (d, 2H), 6.9 (d, 1H), 7.06 (dd, 2H), 735 (dd, 2H), 7.73 (dd , 1 H), 7.81 (br, 1 H), 8 16 (d, 1 H)

 mp: 9 3-9 4 ° C

<Compound Na 0 2 1>

Ή-NMR (CDC) ₃ ): 1.26 (t, 3 H), 2.68 (q, 2 H), .32 (s, 3 H), 4.16 (s, 3 H) ) 4.22 (s, 2H), 4.5 (d, 2H), 6.92 (d, 1H), 7.08 (dd, 2H), 7.35

(dd, 2H), 7.57 (br, 1H), 775 (dd, 1H), 8.16

(d, 1 H)

 m p: 1 1 0-1 1 2 ° C

<Compound No. 0 2 2>

'H-NMR (CD C 1 3):. 2. 3 1 (s, 3 H), 3. 5 2 (s, 1 H), 1 5 (s, 3 H), 4. 6 2 (d, 2 H) 7.33 (d, 1 H), 7.6 (br, 1 H), 7.68 (dd, 1 H), 8.40 (d, 1 H)

 mp: 19 2—19 3 C

<Compound Na 0 2 3>

_{'H-NMR (CDC 1 3} ):. 2. 3 1 (s, 3 H), 3. 5 5 (s, 1 H), 1 6 (s, 3 H), 4. 7 0 (dd, 2 H), 7.48 (t, 1H), 7.6 (br, 1H)

 m p: 1 6 6-1 6 7 ° C

<Compound Na 0 2 4>

_{Ή-NMR (CD C 1 3} ):. 2. 2 6 (s, 3 H), 4. 0 2 (s, 3 H), 5 6 (d, 2 H), 5. 3 6 (dd, 2 H), 5.42 (dd, 1H); 6.34 (br, 1H), 656 (dd, 1H), 6.96 (d, 1H), 7.28 (dd, 1H), 743 (ddd, 1 H), 7.47 (ddd, 1H), 7.56 (d, 1H) _; 7.72 (dd, 1H), 7.76 (s, 1H) 7.82 (dd, 1H), 7, 86 (d, 1H), 8.16 (d, 1H) mp: 125-126 ° C

 <Compound No. 0 25>

_{Ή-NMR (CDC 1 3)} 2 7 (s, 3 H), 4. 0 3 (s, 3 H), 4. 5 7 (d, 2 H), 5. 3 8 (dd, 2 H), 5.42 (dd, 1 H), 6.37 (br, 1 H), 6.57 (dd, l H), 6.98 (d, 1 H),

7.31-7.55 (m, 4 H) 7.75 (d d, 1 H), 8.14 (d, 1 H)

 mp: 94.0-94.5 ° C

 <Compound No. 0 26>

_{Ή-NMR (CDC 1 3)} : 2 2 6 (s, 3 H), 4. 0 2 (s, 3 H)

4.59 (d, 2 H), 5.39 (d d, 1 H), 5.43 (d d, 1 H),

6.43 (br, 1 H), 65 7 (d d, 1 H) 7.33 (d, 1 H),

7.67 (d, 1H), 8, 36 (d, 1H)

 m p: 1 1 0-1 1 1 ° C

 <Compound No. 0 2 7>

_{'H- NMR (CDC 1 3)} 1. 2 2 (t, 3 H) 6 4 (q, 2 H), 4. 0 4 (s, 3 H), 4. 5 5 (d, 2 H), 5.36 (dd, 1H) 5.41 (s, 1H), 6.38 (br, 1H), 6.57 (m, 1H), 696 (d, 1H) H), 7.28 (dd, 1H), 7.40 (ddd, 1H), 748 (ddd, 1H), 7.56 (d, 1H), 7.72 (dd, 1H), 777-17.85 (m, 1H), 7.88 (d, 1H), 8.15 (d, 1H) mp: 1 1 2-1 1 3 ° C

 <Compound Na 0 2 8>

_{Ή-NMR (CDC 1 3)} : 1. 2 2 (t, 3 H), 2. 6 3 (q, 2 H), 4.04 (s, 3 H), 4.56 (d, 2 H), 5.37 (dd, 1 H), 5.42 (s, 1 H), 6.90 (br , 1H), 6.35-6.57 (m, 1H) 6.97 (d, 1H), 7.31-7.55 (m, 4H), 7.6 6 (dd, 1 H), 8.14 (d, 1 H)

 mp: 9 3. C

 <Compound Na 0 2 9>

_{Ή-NMR (CDC 1 3)} : 1 3 2 (s, 9 H), 2. 3 0 (s, 3 H) 3. 4 4 (s, 1 H), 4. 1 7 (s, 3 H) , 4.60 (d, 2 H), 7.8 (dd, 2 H), 7.38 (dd, 2 H), 7.55 (br, 1 H)

 m p: 90 ° C

 <Compound Na 0 3 0>

_{Ή-NMR (CDC 1 3)} : 2. 3 0 (s, 3 H), 2. 3 3 (s, 3 H) 3. 4 4 (s, 1 H), 4. 1 6 (s, 3 H ), 4.58 (d, 2H), 6.

2 (dd, 2H), 696 (dd, 2H), 7.13 (dd, 2H), 7.8 (dd, 2H), 754 (br, 1H)

 m p: 70 ° C

 <Compound No. 0 3 1>

_{Ή-NMR (CDC 1 3)} : 1. 2 6 (t, 3 H), 1. 3 2 (s, 9 H), 2. 7 0 (q, 2 H), 3. 4 4 (s, 1 H), 4.17 (s, 3H), 4.60 (d, 2H), 7.28 (d, 2H), 7.37 (d, 2H), 7.5 7 (br, 1H)

 m p: 7 3-75 ° C

 <Compound Na 0 3 2>

_{'H - NMR (CDC 1 3} ): 1. 2 6 (t, 3 H), 2. 3 3 (s, 3 H), 2. 6 9 (q, 2 H), 3. 4 5 (s, 1H), 4.17 (s, 3H), 4.58 (d, 2H), 6.91 (dt, 2H), 6 • 96 (dt, 2H), 7. 13

(d, 2H), 729 (d, 2H), 7.56

mp: 82 ° C <Compound NQ.0 3 3>

_{Ή-NMR (CDC 1 3)} : 1. 3 2 (s, 9 H), 2. 2 6 (s, 3 H), 4. 0 3 (s, 3 H), 4. 5 7 (d, 2 H), 5.39 (dd, 2H), 6.

2 7 (br, 1 H), 6.59 (dd, 2 H), 7.25 (dd, 2 H), 7.

3 9 (dd, 2H)

 mp: 90.5-910C

 <Compound Na 0 3 5>

_{Ή-NMR (CDC 1 3)} : 1. 2 2 (t, 3 H), 1. 3 2 (s, 9 H), 2. 6 4 (q, 2 H), 4. 0 4 (s, 3 H), 4.57 (d, 2H), 5.3

5 (dd, 1 H), 5.39 (dd, 1 H), 6.30 (br, 1 H), 6.58 (dd, 1 H), 7.25 (d, 2 H ), 7.38 (d, 2 H)

 m p: 5 9-6 1 ° C

 <Compound Na 0 3 6>

_{Ή-NMR (CDC 1 3)} : 1. 2 2 (t, 3 H), 2. 3 4 (s, 3 H), 2. 6 4 (q, 2 H), 4. 0 4 (s, 3 H), 5.34 (dd, 1H), 5.39 (dd, 1H), 6.32 (br, 1H), 6.56 (dd, 1H), 6.9 1 (dt, 2H), 6, 95 (dt, 2H), 7.14 (d, 2H), 7.2

6 (d, 2 H)

 mp: 104-105 ° C

 <Compound No. 0 3 7>

 'H-NMR (CDC): 2.24 (s, 3 H), 4.05 (s, 3 H), 4.56 (d, 2 H), 5.42 (d, 1 H ), 5.62 (d, 1 H), 6.60 (br, 1 H), 6.95 (d, 1 H), 7.28 (dd, 1 H), 7.40 One 7.50 (m, 2H), 7.56 (d, 1H), 7.55 (d, 1H), 7.

7 0-7.89 (m, 4 H), 8.16 (d, 1 H)

 m p: 9 1-9 2 ° C

 <Compound Na 0 3 8>

_{'H-NMR (CDC 1 3} ) δ (ppm) 30 (3 H, s), 3.49 (1 H, s), 4.15 (3 H, s), .57 (2 H, d), 6.92 (1 H, d), 7.07 (2H, d), .35 (2H, d), 7.58 (1H, bt), 7.73 (1H, dd), .16 ( 1 H, d)

 mp: 1 30.5-1 31.4. C

<Compound No. 0 3 9>

 'H-NMR (CDC "):

 . 30 (s, 3 H), 3.49 (s, 1 H), 4 15 (s, 3 H), .58 (d, 2 H), 6.93 (d, 1 H ), 703 (dt, 2 H), .50 (dt '2 H), 758 (b 1 H) 7.73 (dd, 1 H) .16 (d, 1 H),

 mp: 150-15 2 ° C

<Compound No. 04>

'H-NMR (CD C 1 3):

 . 36 (s, 3 H), 3.48 (s, 1 H), 39 1 (s, 3 H). 15 (s, 3 H), 4.56 (d, 2 H) , 686 (d, 1 H) .93 (dt, 2 H), 7.06 (dt, 2 H) 7.56 (br, 1 H) .69 (dd 1 H), 8 1 6 (d, 1 H)

 mp: 1 3 6-1 3 7 ° C

 <Compound No. 0 4 1>

 'H-NMR (CDC "):

1.26 (t, 3H), 2.69 (q, 2H), 349 (s, 1H)

 . 16 (s, 3 H), 4.58 (d, 2 H), 69 (d, 1 H). 10-7.15 (m, 2 H), 7. 17- 7.2 4 (m, 1 H)

 . 3 7-7.44 (m, 2H), 7.59 (br, 1H),

7.71 (d d '1H), 8.18 (d, 1H)

mp: 1 1 3 — 1 1 4 ° C <Compound No. 04 2>

_{Ή-NMR (CD C 1 3} ):

 . 26 (t, 3H), 2.35 (s, 3H), 2.70 (q, 2H), .48 (s, 1H), 4.16 (s, 3 H), 4.57 (d, 2H), .88 (d, 2H), 7.02 (dd, 2H), 7.20 (dd, 2H). , 1 H), 7.69 (dd, 1 H), 8.16 (d, 1 H) mp: 1 35-13 36 ° C

 <Compound No. 0 4 3>

'H-NMR (CD C 1 3):

 . 26 (t, 3H), 2.70 (q, 2H), 3.48 (s, 1H), .81 (s, 3H), 4.16 (s, 3 H), 4.56 (d, 2H), .86 (d, 1H), 6.92 (dd, 2H), 7.05 (dd, 2H). 56 (br , 1 H), 7.68 (dd, 1 H), 8.15 (d, 1 H) mp: 90-91 ° C

 <Compound No. 0 4 4>

 'H-NMR (CD C ") 6 (p P m):

 .6 (3H, s), 2.49 (3H, s), 2.70 (2H, q), .49 (1H, s), 4.16 (3H, s) ), 4.57 (2H, d), .90 (1H, d), 7.07 (2H, d), 7.30 (2H, d), .59 (1 H, bt), 7.71 (1H, dd), 8.17 (1H, d) mp: 87.0-89.2 ° C

<Compound No. 0 4 5>

_{Ή-NMR (CD C 1 3} ):

1.26 (t, 3H), 2.70 (q, 2H), 3.49 (s, 1H), 4.16 (s, 3H), 4.57 (d , 2 H), 6.90 (d, 2 H),

7.07 (d, 2H), 7.10 (s, 2H), 7.59 (br, 1H),

7.72 (d d, 1 H), 8.15 (d, 1 H)

mp: 1 4 2 1 1 4 3 ° C Compound Να 0 4 6>

_{Ή-NMR (CD C 1 3} ):

 . 26 (t, 3H), 2.70 (q, 2H), 350 (s, 1H), .16 (s, 3H), 4.58 (d, 2H ), 692 (d, 1H), .02 (d, 2H), 7.50 (d, 2H), 760 (br, 1H), .73 (dd1H ), 8.16 (d, 1 H)

 mp: 1 2 4) C

<Compound No. 0 4 7>

_{'H-NMR (CDC 1 3} ):

. 26 (t, 3H), 2.70 (q, 2H), 3.05 (s, 1H), .49 (s, 1H), 4.16 (s, 3 H), 4.59 (d, 2 H), .93 (d, 1 H), 7.08 (dd, 2 H), 7.52 (dd, 2 H). 60 (br 1 H), 7. 7 4 ( dd, 1 H), 8. 1 8 (d, 1 H) mp: 1 3 6 5 C

 <Compound No. 0 4 8>

 'H-NMR (CD C 13):

 . 26 (t, 3H), 2.70 (q, 2H), 349 (s, 1H), .97 (s, 3H), 4.16 (s, 3H) ), 4.58 (d, 2H), .93 (d, 1H), 7.13 (dt, 2H), 7.60 (br, 1H) .61 (dt, 2H) H), 7.74 (dd, 1H), 8.06 (s, 1H). 18 (d, 1H)

 mp: 1 2 5-1 2 7 ° C

<Compound Na 0 4 9>

 'H-NMR (CD C 13):

. 26 (t, 3H), 2.70 (q, 2H) 45 (s, 1H), .17 (s, 3H), 4.59 (d, 2H) 0 0-7.09 (m, H), 7.29—7.39 (m, 4H), 757 (br, 1H) mp: 101-103 ° C Compound NQ.50>

_{Ή-NMR (CD C 1 3} ):

1.26 (t, 3H), 2.48 (s, 3H), 2700 (q, 2H)

3.46 (s, 1 H), 4 17 (s, 3 H), 4.59 (d, 2 H)

 6.94 (d, 2H), 696 (d, 2H), 7.26 (d, 2H)

 7.3 1 (d, 2H), 758 (br, 1H)

 mp: 115-116 ° C or less The following are examples of formulations of the insecticide, acaricide, and fungicide for agricultural and horticultural use containing the compound of the present invention as an active ingredient. The forms of acaricides and fungicides are not limited to those described below.

 <Formulation example 1: wettable powder>

 20 parts by weight of compound of the present invention, Carplex # 80D (white carbon, Shionogi & Co., Ltd., trade name) 20 parts by weight, ST Kaolin clay (Kaolinite, Tsuchiya Kaolin Co., trade name) 5 2 parts by weight, Solpol 904 K (Anionic surfactant, Toho Chemical Co., Ltd., trade name) 5 parts by weight, Lunox P65L (Anionic surfactant, Toho Chemical Co., trade name) 3 parts by weight were blended and uniformly mixed and ground to obtain a wettable powder of the active ingredient of 20% by weight.

 <Formulation Example 2: Powder>

 2 parts by weight of the compound of the present invention, 93 parts by weight of clay (manufactured by Nippon Talc), 5 parts by weight of Carplex # 80D (white carbon, Shionogi & Co., Ltd., trade name) are uniformly mixed and ground. A powder of 2% by weight of the active ingredient was produced.

 <Formulation Example 3: Emulsion>

20 parts by weight of the compound of the present invention and 15 parts by weight of solpol 3005 X (mixture of nonionic surfactant and anionic surfactant, Toho Chemical Co., Ltd.) with 35 parts by weight of xylene Was dissolved in a mixed solvent consisting of 30 parts by weight of dimethylformamide and 30 parts by weight of dimethylformamide to obtain an emulsion containing 20% by weight of the active ingredient. <Formulation Example 4: Flowable agent>

 30 parts by weight of the compound of the present invention and 5 parts by weight of sorbol 9004.7K, Sorbon T-120 (nonionic surfactant, Toho Chemical Co., Ltd., 3 parts by weight), 8 parts by weight of ethylene glycol and 44 parts by weight of water is wet-pulverized with a Dyno mill (Shinmaru Enterprises), and 10 parts by weight of a 1% by weight aqueous solution of xanthan gum (natural polymer) is added to the slurry-like mixture. As a result, a 20% by weight of a fusible agent was obtained.

 <Test Example 1: Insecticidal effect on the larvae of the flying pills>

 Rice sprout seedlings were set in a glass cylinder (inner diameter 3 cm x length 17 cm), and five larvae of the 4th-stage Toby louka were released. A water dilution (0.5 mL) of the insecticide (emulsion) of the present invention produced according to the formulation of Preparation Example 13 was sprayed onto the above-mentioned glass cylinder using a spray tower (manufactured by Mizuho Rika) (1 concentration, 2 repetitions). Five days after the treatment, the larvae were examined for viability and agony, and the killing rate (%) was determined by assuming that the agony worms were killed by 1/2. Table 1 shows the results.

 Table 2: Insecticidal effect on the larvae of the flying force

 Compound No. Concentration (Ppm) Insecticidal rate (%)

 0 0 1 5 0 0 1 0 0

 0 0 3 5 0 0 1 0 0

 0 0 5 5 0 0 1 0 0

 0 0 6 5 0 0 1 0 0

 0 1 7 5 0 0 1 0 0

 0 1 8 5 0 0 1 0 0

 0 1 9 5 0 0 1 0 0

 0 2 1 5 0 0 1 0 0

 0 2 3 5 0 0 1 0 0

 0 2 6 5 0 0 1 0 0

 0 2 7 5 0 0 1 0 0

0 2 8 5 0 0 1 0 0 Table 1 2 (Continued) Insecticidal effect of Toby mouth force on larvae

 <Test Example 1: Insecticidal effect on larvae of Japanese moth>

 Formulation Example 1-Cabbage cut leaves (diameter 6 cm) were immersed in a water dilution of the insecticide (wettable powder) of the present invention manufactured according to the formulation of Example 1 for 1 minute. After immersion, it was air-dried and placed in a plastic cup (7 cm in inside diameter). Five third-instar larvae of the Japanese moth were released into this cup (1 concentration, 2 repetitions). After 4 days from the release, the larvae were examined for life and death and agony, and the killing rate (%) was calculated with 1/2 of the agony insects killed. Table 13 shows the results.

 Table 1 3: Insecticidal effect on the larvae of the diamondback moth

 Compound No. Concentration (Ppm) Insecticidal rate (%)

 0 0 1 5 0 0 1 0 0

 0 0 3 5 0 0 1 0 0

 0 0 5 5 0 0 1 0 0

 0 0 6 5 0 0 1 0 0

 0 1 8 5 0 0 1 0 0

 0 1 9 5 0 0 1 0 0

 0 2 3 5 0 0 1 0 0

 0 2 4 5 0 0 1 0 0

 0 2 7 5 0 0 1 0 0

 0 2 8 5 0 0 1 0 0

 0 3 4 5 0 0 1 0 0

 0 3 6 5 0 0 1 0 0

 0 3 7 5 0 0 1 0 0

0 3 8 5 0 0 1 0 0 Table 1 3 (continued): Insecticidal effect on Japanese larvae of Japanese moth

 Test Example 1: Acaricidal effect on adult adults

 On the cut leaves of kidney beans (3 cm in diameter), 10 adult females were released. Preparation Example 1 A solution (3.5 mL) prepared by diluting the acaricide of the present invention (water dispersible powder) prepared according to the prescription of 1 to a predetermined concentration with water was placed on the above-mentioned cut leaves by a rotary spraying tower ( (Mizuho Rika) (1 concentration, 2 replicates). Twenty-four hours after treatment, adult mortality was examined and the kill rate (%) was determined. Table 14 shows the results.

 Test Example 1 4: Acaricidal effect on the eggs of Nami-nada

 Five adult females were released on cut leaves (3 cm in diameter) of kidney beans. After release, eggs were laid on cut leaves for 20 hours, and then female adults were removed. Formulation Example 11 A solution (3.5 mL) prepared by diluting the acaricide (wetting agent) of the present invention to a predetermined concentration with water, prepared according to the formulation of Example 1, was spread on the above-mentioned disk by a rotary sprayer ( (Mizuho Rika)

(1 concentration, 2 replicates). Eight days after the treatment, the number of unhatched eggs and the number of hatched larvae were examined, and the ovicidal rate (%) was determined. Table 14 shows the results. . Table 4: Acaricidal effect on adult and egg of Nami-nada

 * 1: Not implemented

 <Test Example 4: Rice blast control effect test>

A wettable powder, prepared in the same manner as in Formulation Example 1, was diluted to a predetermined concentration with 3 to 4 leaf stage rice (cultivar: Akinishi) grown in pots with a diameter of 6 cm. Foliage was sprayed at a rate of 10 ml. After air-drying, the spore suspension of rice blast (Pyricu 1 ariaoryzae) cultivated on the oat mill decoction medium is sprayed and then kept in a moist chamber for 24 hours to infect it. Leave for 5-7 days Was.

 Evaluation evaluated the diseased area ratio of each leaf, and calculated the control value by the following formula. Table 5 shows the results.

 (A-B)

Control value (%) X 100

 B

 A: Average disease area ratio of untreated area

 B: Average disease area ratio of treatment area

 Table 1 5: Effect on rice blast

 Compound No. Concentration (ppm) Control value (%)

 0 0 3 2 5 0 9 2

 0 1 7 2 5 0 9 6

 0 1 8 2 5 0 1 0 0

 0 2 4 2 5 0 9 6

 0 2 5 2 5 0 1 0 0

 0 3 0 2 5 0 9 0

 0 3 1 2 5 0 8 7

 0 3 2 2 5 0 1 0 0

 0 3 4 2 5 0 9 5

 0 3 7 2 5 0 9 4

 0 3 8 2 5 0 9 0

 0 3 9 2 5 0 9 0

 0 4 0 2 5 0 8 9

 0 4 3 2 5 0 9 8

 0 4 4 2 5 0 9 4

 0 4 6 2 5 0 9 8

 0 4 7 2 5 0 9 1

 0 4 8 2 5 0 9 2

0 4 9 2 5 0 9 1 <Test Example 5: Wheat rust control effect test>

 Formulation of a wettable powder prepared in the same manner as in Example 1 was diluted to a prescribed concentration in 1-2-wheat wheat (cultivar: Norin 61) grown in pots with a diameter of 6 cm. Foliage was sprayed at a ratio of Om1. After air-drying with chemicals, spraying and spraying a spore suspension obtained by grinding wheat leaves infected with wheat leaf rust (Pucciniarecondita), keeping in a moist chamber at 22 ° C for 24 hours, and then in a greenhouse To? Left for ~ 10 days. For evaluation, the diseased area ratio of each leaf was evaluated, and the control value was calculated in the same manner as in Test Example 1. The results are shown in Table-6.

 Table 1-6: Effect on wheat leaf rust

 Compound No. Concentration (P P m) Control value (%)

 0 0 1 2 5 0 1 0 0

 0 0 5 2 5 0 1 0 0

 0 1 7 2 5 0 1 0 0

 0 2 3 2 5 0 1 0 0

 0 2 4 2 5 0 1 0 0

 0 2 5 2 5 0 1 0 0

 0 2 6 2 5 0 1 0 0

 0 2 7 2 5 0 1 0 0

 0 2 8 2 5 0 1 0 0

 0 2 9 2 5 0 1 0 0

 0 3 1 2 5 0 1 0 0

 0 3 2 2 5 0 1 0 0

 0 3 3 2 5 0 1 0 0

 0 3 4 2 5 0 1 0 0

 0 3 6 2 5 0 1 0 0

 0 4 0 2 5 0 1 0 0

 0 4 2 2 5 0 '1 0 0

0 4 3 2 5 0 1 0 0 Table 1 6 (continued): Effect on wheat leaf rust

 <Test Example 6: Tomato disease control effect test>

 Tomatoes of 3 to 5 leaf stage (variety: Red Cherry) grown in pots with a diameter of 9 cm, a dilution of the prescribed concentration prepared in the same manner as in Formulation Example 1 at a ratio of 10 ml / bottom With foliage. After air-drying with chemicals, spray inoculation with a zoospore sac suspension obtained from tomato leaves infected with Phy tophthorainfestans, keeping in a moist chamber at 22 ° C for 24 hours, and then in a greenhouse In the c evaluation, which was left on the water tank for 5 to 7 days, the diseased area ratio of each leaf was evaluated, and the control value was calculated in the same manner as in Test Example 1. Table 7 shows the results.

 Table 1 7: Control effect on tomato blight

 Compound No. Concentration (ppm) Control value (%)

 0 0 4 2 5 0 1 0 0

 0 0 5 2 5 0 1 0 0

 0 0 6 2 5 0 1 0 0

 0 1 5 2 5 0 1 0 0

 0 1 6 2 5 0 1 0 0

 0 1 9 2 5 0 1 0 0

 0 2 0 2 5 0 1 0 0

 0 2 1 2 5 0 1 0 0

 0 2 2 2 5 0 1 0 0

0 2 3 2 5 0 1 0 0 Table 1 7 (continued): Control effect against tomato blight

Industrial applicability

 INDUSTRIAL APPLICABILITY The novel pyrazole compound of the present invention has an extremely excellent controlling effect on various plant pathogenic bacteria, pests, etc., and is particularly useful as an agricultural and horticultural insecticide, acaricide, and fungicide. .

Claims

The scope of the claims

1. A pyrazole compound represented by the following general formula (I) c

In the formula (I), R ¹ and R ² each independently represent a hydrogen atom or a C, to C ₄ alkyl group;

 Y represents a group represented by the following general formula (Π) or a group C≡C—,

: = αΐ)

R ⁷ ,

Wherein R ⁷ and R ⁸ are each independently a hydrogen atom, a C, to ( ₄ alkyl group, a halogen atom, a C, to C ₄ alkoxy group, a C _{2 to} C ₇ acyl group; group shown, C, and Ashiruokishi group -C _7.]

R ³ is a hydrogen atom, C, alkyl group -C _6, halogen atom, C, haloalkyl groups -C _4, an alkenyl group of C ₂ ~ C _5, alkynyl group of _{C 2 ~C 5, C 3 ~} C _S cycloalkyl group, d to C ₇ hydroxyalkyl group and protected form thereof, C ₅ or C ₆ hydroxyxine chloroalkyl group, (C, to C ₄ alkylthio) C, to C ₄ alkyl group, , ~ C ₇ aminoalkyl group, (C, ~ (: ₄ alkylamino) C, ~ C ₇ alkyl group, di (C, ~ C ₄ alkylamino) C, ~ C ₇ alkyl group, (C, ~ C ₇ acylamino) C, to C ₇ alkyl group, C ₂ to ( ₇ acyl group,

(C, ~ c ₆ alkoxy) carbonyl group, (c, ~ C ₆ alkylamino) carbonyl group, di (C, ~ C ₄ alkylamino) carbonyl group, carboxyl group, formyl group and protected form thereof, C ₃ ~ ( : A trialkylsilyl group of; or C, to (: an alkyl group of, C, to (: an alkoxy group of ₄ , a halogen atom, a nitro group, a cyano group, C, to (: ₄ haloalkyl group, d to C ₄ haloalkoxy group, phenyl group, phenoxy group, C ₂ to (: 7 acyl group, (Ci to (: 4 alkoxy) carbonyl group, c, to be substituted with a selected Bareru substituents from the group consisting of an alkylthio group, and triflate Ruo b methylthio group c ₄ showed good Fuyu two group,

R ⁴ represents a hydrogen atom, an alkyl group -C _4, Ashiru group of _{C 2 ~ C 7, (C} , ~ c 4 alkoxy) carbonyl group or (d -C ₄ alkoxy) C, -C ₄ al Kill group ,

R ⁵ and R ⁶ each independently represent a hydrogen atom or a C, to C ₄ alkyl group;

A represents a group represented by the following general formulas (a) to (! Πj). One FT

 (Illa) (Illb) (IIIc) (Hid) (Hie)

 (Illf) (nig) (Illh) (Illi) (Illj)

[In the formulas (Ma) to (! Π j), R ⁹ is a hydrogen atom, an alkyl group of Ci Cs, C, to (: an alkoxy group of ₄ , a halogen atom, a haloalkyl group of Ci C *, C, to C ₄ ? haloalkoxy groups, C ₃ -C cycloalkoxy group, (:, ~:;! alkylthio group; or C, ~ (: ₄ alkyl group, Aruke alkenyl group of C ₂ ~C _5, C ₂ ~ (: ₅ alkynyl groups, ~ C ₄ alkoxy groups, ~

A C 4 haloalkyl group, a d-C 4 haloalkoxy group, a halogen atom, a phenyl group, a phenoxy group, a cyano group, a nitro group, a formyl group and a protected form thereof, a hydroxy group, a C ₂ -C ₇ acyl group, A group represented by the following general formula (W): ~ (: ₄ alkoxy) carbonyl group, d to C ₄ alkylthio group and trifluoromethylthio group Represents a phenoxy group or a naphthyloxy group which may be substituted,

R '° represents a hydrogen atom, an alkyl group or C, Haroaru kill groups -C ₃ of -C _6,

R ¹¹ represents a hydrogen atom, a d-C ₄ alkyl group or a paratoluenesulfonyl group. ]

 OR, 1'2

 /

 N

 (IV)

 People, 13

[In the formula (IV), R ¹² represents a d-C ₄ alkyl group;

R ¹³ represents a hydrogen atom or a C, to C ₄ alkyl group. ]

2. A virazole compound represented by the following general formula (I-11).

In the formula (I—1), R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ and R ⁹ have the same meaning as defined in the general formula (I), and W is a group CH or a nitrogen atom Is shown.

3. R ¹ and R ² are each independently an alkyl group of C, to (: ₄ , R ³ , R ⁴ , R ⁵ and are simultaneously a hydrogen atom, and W is a group CH or a nitrogen atom. R ⁹ is a halogen atom, d to C ₄ alkyl group, C, to C ₄ haloalkyl group, d to C ₄ alkylthio group; or C _{2 to} C ₅ alkynyl group, represented by the general formula (IV) Okishimu groups and C, Birazo Ichiru according to claim 2 to Toku徵that the are optionally Fuwenokin group or Nafuchiruokishi group substituted with a substituent Bareru selected from the group consisting of an alkoxy group -C ₄ Compound.

4. An agricultural and horticultural drug containing the pyrazolyl compound according to any one of claims 1 to 3 as an active ingredient.

5. An agricultural and horticultural pharmaceutical composition comprising an effective amount of the pyrazole compound according to any one of claims 1 to 3 and an agricultural and horticultural agricultural chemical adjuvant.

6. An insecticide containing the pyrazole compound according to any one of claims 1 to 3 as an active ingredient.

7. An acaricide containing the pyrazole compound according to any one of claims 1 to 3 as an active ingredient.

8. A fungicide containing the birazol compound according to any one of claims 1 to 3 as an active ingredient.

9. Use of the pyrazole compound according to any one of claims 1 to 3 for controlling pests in the agricultural and horticultural fields.