WO2003062222A1

WO2003062222A1 - Pyrazolecarboxamides, intermediates thereof and pesticides containing the same as the active ingredient

Info

Publication number: WO2003062222A1
Application number: PCT/JP2003/000428
Authority: WO
Inventors: Eiji Takizawa; Itaru Okada; Kazuhiko Kikutake; Toshiki Fukuchi
Original assignee: Nihon Nohyaku Co., Ltd.
Priority date: 2002-01-21
Filing date: 2003-01-20
Publication date: 2003-07-31
Also published as: JP2003277362A

Abstract

Compounds represented by the following general formula (I) which have a high bactericidal activity on various pathogenic microorganisms as well as high insecticidal and miticidal activities and are useful in controlling pests; pesticides containing these compounds as the active ingredient; and intermediates represented by the following general formula (II): (I) (II) wherein each substituent has the meaning as defined in the description.

Description

Description Pyrazolecarboxamides, intermediates thereof, and pesticidal agents containing the same as active ingredients

The present invention relates to novel pyrazolecarboxamides and a pesticidal composition containing these as an active ingredient. The novel pyrazolecarboxamides of the present invention are useful as agricultural and horticultural fungicides, insecticides and acaricides. Background art

In the agricultural and horticultural field, various fungicides, insecticides, and acaricides for controlling various pests have been developed and put to practical use. However, conventional agricultural chemicals have not been able to be said to satisfy the requirements such as effect, spectrum, residual effect, etc., or reduction of the number of applications and the amount of applied chemicals.

In addition, the emergence of 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 and rice, various types of insecticides such as carbamates, pyrethroids, benzoyl perreas, organic chlorides, and organic phosphorus are used. Resistance to various pests that have acquired resistance and various types of fungicides such as, for example, triazoles, imidazoles, pyrimidines, benzimidazoles, dicarboximides, and phenylamides Various pathogens have emerged in various places, and it has become difficult year by year to control various pests caused by these resistant pests.

New pesticides that exhibit sufficient control effects even at low doses against various pathogens and pests that have acquired resistance to conventional general-purpose agricultural and horticultural insecticides and fungicides, and that have little adverse effect on the environment are constantly appearing. Is desired. It is known that N-benzylpyrazole-5-potoxolemide derivatives have insecticidal and acaricidal activity (see, for example, JP-A-64-25763). The publication discloses the following compounds having insecticidal and acaricidal activity.

Tephumpyra) (generic name)

It is also known that the following compounds having a phenoxy group show insecticidal and acaricidal activity (see, for example, JP-A-3-81266).

(Torphine Pilad) (generic name)

On the other hand, N_pyridylmethylpyrazole-15-carboxamide derivatives having a similar structure to the compound of the present invention include, for example, compounds of the present invention represented by the following general formula (I) as represented by the following structural formula (III) substituents corresponding to R ⁵ are those alkyl groups, insecticidal, acaricidal and disease are also disclosed as of having bactericidal activity represented by base and mildew (JP-2-62876 discloses the compound No. 34).

And compounds having both fungicidal and insecticidal and acaricidal activity are very important in agricultural and horticultural applications.

Disclosure of the invention

An object of the present invention is to provide a new substance which exhibits a high control effect against various pathogens and is effective for controlling pests such as insects and dapa, and which is particularly resistant to conventional insecticides. An object of the present invention is to provide a highly safe substance which exhibits a high control effect against various pests showing the above, exhibits an effect even at a low dose, and has reduced problems such as residual toxicity and environmental pollution.

The present inventors have conducted intensive studies to solve the above-mentioned problems, and as a result, novel pyrazolecarboxamides having a phenylpyridine skeleton and having a specific combination of substituents satisfy the above-mentioned requirements. It has been found that it has sterilizing, insecticidal and acaricidal activities, and has completed the present invention.

The present invention relates to a pyrazolecarboxamide compound represented by the following general formula (I) or an acid addition salt thereof.

In the formula, R ¹ represents an alkyl group of

R ² represents an alkyl group, a haloalkyl group or a CCS in § Norekokishi group C ₁ -C ₅ a C ₁ -C _5,

R ³ represents a hydrogen atom or an alkyl group ～〇 _3,

R ⁴ is ^ ～〇 ₅ alkyl group, a haloalkyl group or a halogen atom -, provided that when m is 2 or more, R ⁴ may be the same or different, R ⁵ represents an alkyl group, a haloalkyl group, an alkoxy group, an alkoxyalkoxy group, a haloalkoxy group, a hydroxyl group, an acyloxy group, a halopropyloxy group, an alkylthio group, a formyl group,

^: A group represented by (wherein, R ⁶ and R ⁷ may be the same or different, a hydrogen atom or an alkyl group ～〇 _5, respectively) that in N-0-R ^7, or two Adjacent but joined together or ^F

, A group represented by 0, provided that when n is 1, R ⁵ is not an alkyl group, and when n is 2 or more, R ⁵ may be the same or different,

Hi indicates an integer from 0 to 3,

n represents an integer of 1 to 5,

p represents 0 or 1,

X represents a hydrogen atom, C～C ₃ alkyl group, ～〇 ₃ alkoxy group or a halogen atom.

Further, the present invention relates to a phenylpyridylmethylamine compound represented by the following general formula (II) or an acid addition salt thereof.

Wherein R ³ , R ⁴ and m are as defined in the above general formula (I) R ⁸ represents a haloalkoxy group.

Furthermore, the present invention relates to a composition comprising the above-mentioned pyrazolecarboxamide compound or an acid addition salt thereof, and an agricultural chemical adjuvant.

Furthermore, the present invention relates to the use of the above-mentioned pyrazolecarboxamide compound or its caro salt with acid as a pesticide.

Further, the present invention relates to a method for controlling pests, which comprises contacting an effective amount of the pyrazolecarboxamide compound or an acid addition salt thereof with a pest. BEST MODE FOR CARRYING OUT THE INVENTION

Hereinafter, the present invention will be described in detail.

In the pyrazolecarboxamide compound of the present invention represented by the general formula (I) (hereinafter abbreviated as the compound represented by the general formula (I)), examples of R ¹ include a methyl group and an ethyl group , N-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, 2-methylbutyl, 3-methylbutyl, isopentyl, 2-ethylpropyl , neopentyl group, 2, 2-dimethylpropyl group, 2-methyl isobutyl group, cyclopropyl group, consequent opening heptyl group, such as consequent opening pentyl (^ ~ Ji ₅ linear or branched alkyl group or a C Examples thereof include a cyclic alkyl group of _{3 to} C _5. Among them, R ¹ is preferably a methyl group.

Examples of R ² include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, 2-methylbutyl, —C _{1 to} C ₅ straight chain such as methylbutyl group, isopentyl group, 2-ethylethyl pill group, neopentyl group, 2,2-dimethylpropyl group, 2-methylisobutyl group, cyclopropyl group, cyclobutyl group, cyclopentyl group, etc. Or a branched alkyl group or a C ₃ -C ₅ cyclic alkyl group; fluoromethyl group, chloromethyl group, bromomethyl group, difluoromethyl group, difluoroethyl Group, trifluoromethyl group, trichloromethyl group, tribromomethyl group, 21-fluoroethyl group, 2,2,2-trifluoroethyl group, 11- (trifluoromethyl) ethyl group, 1,1,2, 3,3,3-hexafluoropropyl group, 2,2,3,3,3-pentafluoropropyl group, 2,2,3,3-tetrafluoropropyl group, 2,2,3,3 A straight-chain or branched-chain haloalkyl group such as 1,2,3,3,4,4,5,5,5-nonafluoropentyl group;ぴ Methoxy group, ethoxy group, _n -propoxy group, isopropoxy group, n-butoxy group, sec-butoxy group, isobutoxy group, tert-butoxy group, n-pentoxy group, 2-methylbutoxy group, 3-methyl Butoxy, isopentoxy, 2-ethylpropoxy, neopent Shi group, 2, 2-dimethyl propoxy group, include straight chain or branched chain alkoxy group ～〇 ₅ and 2-methyl-isobutoxy group. Among them, R ² is preferably a C i -C ₃ linear alkyl group, particularly preferably a methyl group or an ethyl group.

Examples of R ³ include a hydrogen atom; and a _{C i} -c ₃ linear or branched alkyl group such as a methyl group, an ethyl group, an n-propyl group, and an isopropyl group. Of these, a hydrogen atom is preferable as R ³ .

Examples of R ⁴ include methyl group, Echiru group, n- propyl group, an isopropyl group, n- heptyl group, sec- heptyl group, an isobutyl group, tert- butyl group, n- pentyl group, 2-methylbutyl group, 3 - Mechirupuchiru group, isopentyl group, 2-Echirupu port propyl group, a neopentyl group, 2, 2-dimethylpropyl group, a straight-chain or branched-chain alkyl group ～〇 ₅ and 2-methyl isobutyl group; Furuoromechiru group, chloromethane ethyl group , Bromomethyl group, difluoromethyl group, difluoroethyl group, trifluorenemethyl group, trichloromethyl group, tribromomethyl group, 2-fluoroethyl group, 2,2,2-trifluoroethyl group, and 1- (trifluoromethyl) ethyl 1,1,2,3,3,3-hexafluoropropyl group, 2,2,3,3,3-propanol group at pentapentanole , 2,3,3-tetrafluoropropyl group, 2,2,3,3,4,4,4-heptafluorobutyl group, 2,2,3,3,4,4,5,5,5— Straight or branched haloalkyl group of ^ ~ such as nonafluoropentyl group; and fluorine, chlorine, bromine and iodine And a halogen atom such as an atom. Among them, R ⁴ is preferably a hydrogen atom.

Examples of R ⁵ include methyl group, Echiru group, n- propyl group, an isopropyl group, n- Buchinore group, sec- butyl group, an isobutyl group, tert- butyl group, n- Penchinore group, 2-methylbutyl group, 3 —Methylbutyl group, isopentyl group, 2-ethylpentyl group, neopentyl group, 2,2-dimethylpropyl group, 2-methylisobutyl group, etc., a linear or branched alkyl group of; fluoromethyl group, chloromethyl group, Bromomethyl group, difluoromethyl group, difluoroethyl group, trifluoromethyl group, trichloromethyl group, tribromomethyl group, 2-fluoroethyl group, 2,2,2-trifluoroethyl group, 1_ (trifluoromethylinoethyl) ethyl 1,1,2,3,3,3-hexafluoropropyl group, 2,2,3,3,3-pentafluoropropyl group, 2,2,3,3 —Tetrafluoropropyl group, 2,2,3,3,4,4,4-heptaphnoleobutyl group, 2,2,3,3,4,4,5,5,5—nonafluoropentyl Straight-chain or branched-chain haloalkyl groups such as groups; methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, tert-butoxy, n-pentoxy, 2_methylbutoxy group, 3_methylbutoxy group, isobenzyloxy group, 2-ethylpropoxy group, neopentoxy group, 2,2-dimethylpropoxy group, 2-methylisobutoxy group, n_hexyloxy group, n — A straight-chain or branched-chain alkoxy group such as a heptyloxy group or an n-octyloxy group; a straight-chain or branched-chain alkoxyalkoxy group such as a methoxymethoxy group or a 2-ethoxyethoxy group; a difluoromethoxy group; Trifluoromethoxy, fluoromethoxy, trichloromethoxy, tribromomethoxy, 2-fluoroethoxy, 2,2,2-trifluoroethoxy, 2,2,2-trichloroethoxy, 1- (trifluoromethyl ) Ethoxy group, 1,1,2,3,3,3-hexafluoropropoxy group, 2,2,3,3,3-pentaphnolepropoxy group, 2,2,3,3-tetrafluoro Linear or branched haloalkoxy groups such as lopropoxy group, 2,2,3,3,4,4,4-heptafluorobutoxy group; hydroxyl group; acetyloxy group, propionyloxy group, Amoxy groups such as n-butylyloxy group, i-butyroxy group, and piperoyloxy group; halopropoxy groups such as fluoropropenyloxy group, cyclopropinoleoxy group, difluoropropenyloxy group, and dichloropropenyloxy group; methylthio Groups, ethylthio, propylthio, isopropylthio, butylthio, sec-butylthio, isobutynolethio, tert-butylthio, pentylthio, 2-methylbutylthio, 3-methylbutylthio, isopentylthio, 2 Linear or branched alkylthio groups such as -ethylpropylthio group, neopentylthio group, 2,2-dimethylpropylthio group and 2-methylisobutylthio group; forminole group;

R ⁶

(Wherein R ⁶ and R ⁷ may be the same or different and are each a hydrogen atom; or a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n_butyl group, sec-butyl group, isobutyl group, tert-butyl group, n-pentyl group, 2-methylbutyl group, 3-methylbutyl group, isopentyl group, 2-ethylethyl pill group, neopentynole group, 2,2-dimethylpropyl group, 2 — Represents a C i Cs linear or branched alkyl group such as a methinoleisobutyl group); and two adjacent R ⁵ are taken together.

Ό ^Γ

And the group represented by The alkyl group, the haloalkyl group, an alkoxy group, a haloalkoxy group Contact Yopi alkylthio group is preferably a C i Cs, the alkoxyalkoxy group and Ashiruokishi group, what is good Masui c ₂ to c _8. Of these, as R ⁵ , a haloalkyl group of C _{1 to} C = or C! CS An oral alkoxy group is preferred, and a trifluoromethoxy group or a difluoromethoxy group is particularly preferred. The substitution position is preferably the 4-position.

Examples of X include a hydrogen atom; a C Cg linear or branched alkyl group such as a methyl group, an ethyl group, an n-propyl group, and an isopropyl group; a methoxy group, an ethoxy group, an n-propoxy group, linear or branched alkoxy group having ～〇 ₃ such as a propoxy group; a fluorine atom, a chlorine atom, a bromine atom, a halogen atom such as iodine atom. Among them, X is preferably a hydrogen atom.

m is an integer of 0 to 3, and preferably 0 to 2. Here, when m is 0, it means that R ⁴ does not exist.

n is an integer of 1 to 5, preferably 1 or 2.

p is 0 or 1, preferably 0. Here, when p is 0, it means that there is no O binding to N.

The acid to be added to the compound represented by the general formula (I) is not particularly limited as long as it is an acid which can be added. Acetic acid, propionic acid, butyric acid, oxalic acid, adipic acid, dodecandioic acid, lauric acid, Carboxylic acids such as stearic acid, trifluoroacetic acid, fumaric acid, maleic acid, benzoic acid and phthalic acid; sulfonic acids such as methanesulfonic acid, 1,3-propanedisulfonic acid, p-toluenesulfonic acid and dodecylbenzenesulfonate; Inorganic acids such as hydrochloric acid, sulfuric acid, nitric acid, and carbonic acid. In addition, the phenylpyridylmethylamine compound of the present invention represented by the general formula (II) (hereinafter abbreviated as a compound represented by the general formula (II)) and an acid addition salt thereof are described in the above pyrazole carboxy. It is a novel intermediate for producing amides and their acid addition salts.

The acid to be added to the compound represented by the general formula (Π) is not particularly limited as long as it is an acid that can be added. Acetic acid, propionic acid, butyric acid, oxalic acid, adipic acid, dodecandioic acid, lauric acid, Carboxylic acids such as stearic acid, trifluoroacetic acid, fumaric acid, maleic acid, benzoic acid and phthalic acid; methanesulfonic acid, 1,3 Sulfonic acids such as monopropanedisulfonic acid, p-toluenesulfonic acid, and dodecylbenzenesulfonic acid; and inorganic acids such as hydrochloric acid, sulfuric acid, nitric acid, and carbonic acid. The compound of the present invention represented by the general formula (I) is a novel compound and can be produced, for example, according to the following reaction formula.

(1) Reaction of carboxylic acid mouth with phenylpyridylmethylamines

(In the above formulas (IV) and (V), RR ² , R ³ , R ⁴ , R ⁵ , X, m and n are as defined in the above general formula (I).)

The carboxylic acid chlorides (IV) and the phenylpyridylmethylamines (V) can be prepared in the presence or absence of a base, preferably using a solvent, at -10 to 50 ° C, preferably React at 0-25 ° C. The reaction time is about several minutes to 10 hours, but the reaction is completed in a relatively short time.

The solvent is not particularly limited as long as it does not directly participate in the reaction. Examples thereof include aromatic hydrocarbons such as benzene, toluene, and xylene; ketones such as acetone, methyl ethyl ketone, and methyl isobutyl ketone; chloroform, dichloromethane Halogenated hydrocarbons such as water; esters such as methyl acetate and ethyl acetate; or polar solvents such as tetrahydrofuran, acetonitrile, dioxane, Ν, Ν-dimethylformamide, メチル -methylpyrrolidone, dimethyl sulfoxide, pyridine and the like. And the like.

Examples of the base include alkali metal hydrides such as sodium hydride; alkali metal hydroxides such as sodium hydroxide and hydroxylated sodium; sodium carbonate, charcoal Inorganic bases such as alkali metal carbonates such as acid lime; and organic bases such as pyridine and triethylamine.

After the reaction, in order to isolate the target compound of the general formula (I), when a solvent soluble in water is used, the solvent is distilled off under reduced pressure, and water is added. Aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated hydrocarbons such as chloroform and dichloromethane; extracted with esters such as ethyl acetate, washed with water, dilute hydrochloric acid and, if necessary, saturated saline It may be dried with a drying agent such as anhydrous sodium sulfate or anhydrous magnesium sulfate, and the solvent may be distilled off under reduced pressure. When a solvent insoluble in water is used, water is added to the reaction mixture, and the mixture is separated.The organic layer is washed with dilute hydrochloric acid or saturated saline as necessary, and a drying agent such as anhydrous sodium sulfate or anhydrous magnesium sulfate is used. Then, the solvent may be distilled off under reduced pressure. If the residue obtained after distilling off the solvent is purified by recrystallization, suspension washing, column chromatography or the like, the compound represented by the general formula (I) can be obtained.

(2) Synthesis using Suzuki coupling

(VID

(In the above formulas (VI) and (VII), I ¹ , R ² , R ³ , R ⁴ , R ⁵ , X, m and n are as defined in the above general formula (I), and W is Represents a group.)

Carboxamides (VI) and phenylboronic acids (VII) are reacted in the presence or absence of a base or a transition metal catalyst, preferably using a solvent, at 0 to 150 ° C, preferably at room temperature to 120 ° C. .

The solvent is not particularly limited as long as it does not directly participate in the reaction. For example, alcohols such as methanol, ethanol, and isopropanol; benzene, Aromatic hydrocarbons such as toluene and xylene; ketones such as acetone, methyl ethyl ketone and methyl isobutyl ketone; halogenated hydrocarbons such as chloroform and dichloromethane; water; esters such as methyl acetate and ethyl acetate; Or polar solvents such as tetrahydrofuran, acetonitrile, dioxane, N, N-dimethylformamide, N-methylpyrrolidone, dimethylsulfoxide, pyridine and the like.

Examples of the leaving group include a chlorine atom, a bromine atom, an iodine atom, a methylsulfonyloxy group, a ρ-toluenesulfonyloxy group, and a trifluoromethylsulfonoxy group.

As the base, for example, alkali metal hydrides such as sodium hydride; alkali metal hydroxides such as sodium hydroxide and hydroxylamide; inorganic bases such as alkali metal carbonates such as sodium carbonate and carbonic acid rim; And organic bases such as pyridine and triethylamine.

Examples of the transition metal catalyst include palladium compounds such as palladium acetate, dichlorobis (triphenylphosphine) palladium, tetrakis (triphenylphosphine) palladium, and tris (dibenzylacetone) palladium, and bis (triphenylinolephosphine) nickelene. Nickel compounds such as chloride and tetrakis (triphen-^ / phosphine) nickel can be exemplified.

After the reaction, in order to isolate the target compound represented by the general formula (I), when a solvent soluble in water is used, the solvent is distilled off under reduced pressure, and water is added. Aromatic hydrocarbons such as benzene, toluene and xylene insoluble in water; halogenated hydrocarbons such as chloroform and dichloromethane; extracted with esters such as ethyl acetate, washed with saturated saline, and then washed with anhydrous sodium sulfate and anhydrous It may be dried with a desiccant such as magnesium sulfate, and the solvent may be distilled off under reduced pressure. When a solvent insoluble in water is used, water is added to the reaction mixture, and the mixture is separated.The organic layer is washed with saturated saline, dried with a desiccant such as anhydrous sodium sulfate, anhydrous magnesium sulfate, and the like. If the solvent is distilled off under reduced pressure good. If the residue obtained after distilling off the solvent is purified by recrystallization, suspension washing, column chromatography or the like, the compound represented by the general formula (I) can be obtained.

The starting compound represented by the general formula (IV) can be synthesized, for example, by the method described in JP-A-64-25763. Most commercially available products of polyfluoroacids (VII) can be used.

Further, the acid addition salt of pyrazolecarboxamides of the present invention can be produced by the following method.

(I)

氺

(Ι ')

(In the above formula (), RR \ R ³ , RR ⁵ , m and n are as defined in the general formula (I), and Y is an acid.)

The pyrazolecarboxamides (I) and the acid are reacted preferably at 15-50 ° C, preferably 0-25 ° C, using a solvent.

Organic acids and inorganic acids can be used as the acid. Examples of organic acids include carboxylic acids such as acetic acid, propionic acid, butyric acid, oxalic acid, adipic acid, dodecandioic acid, lauric acid, stearic acid, trifluoroacetic acid, fumaric acid, maleic acid, benzoic acid, and phthalic acid; Sulfonic acids such as acid, 1,3-propanedisulfonic acid, p-toluenesulfonic acid, dodecylbenzenesulfonic acid, etc. be able to. Examples of the inorganic acid include hydrochloric acid, sulfuric acid, nitric acid, and carbonic acid.

The solvent is not particularly limited as long as it does not directly participate in the reaction. Examples thereof include aromatic hydrocarbons such as benzene, toluene and xylene; ketones such as acetone, methyl ethyl ketone and methyl isobutyl ketone; chloroform, dichloromethane Water; esters such as ethyl acetate and methyl acetate; or polar solvents such as tetrahydrofuran, acetonitrile, dioxane, N, N-dimethylformamide, N-methylpyrrolidone, and dimethylsulfoxide. be able to.

After the reaction, the solvent is distilled off under reduced pressure, and the crystals are separated by filtration to synthesize benzylamine inorganic acid salt and organic acid salt. This condition is sufficient, but if further purification is desired, high purity pyrazolecarpoxamidic acid addition salt can be synthesized by washing with the above-mentioned organic solvent.

The compound represented by the general formula (V) as a raw material can be synthesized by the following method.

(1) Catalytic hydrogen reduction of fluorocyanoviridines

(VIII) (Va)

(In the above formulas (VIII) and (Va), R ⁴ , R ⁵ , m and n are as defined in the general formula (I).)

The fluorocyanoviridines (VIII) are reacted with hydrogen in the presence of a metal catalyst, aqueous ammonia, preferably using a solvent at 0 to 100 ° C, preferably 25 to 50 ° C. The solvent is not particularly limited as long as it does not directly participate in the reaction. Examples thereof include alcohols such as methanol, ethanol, and isopropanol; aromatic hydrocarbons such as benzene, toluene, and xylene; acetone, methyl ethyl ketone, Ketones such as methyl isobutyl ketone; halogenated hydrocarbons such as chloroform and dichloromethane; water; esters such as methyl acetate and ethyl acetate; or tetrahydrofuran, acetoetrile, dioxane, N, N-dimethyl ^ Examples include polar solvents such as formamide, N-methylpyrrolidone, dimethylsulfoxide, and pyridine.

Examples of the metal catalyst include Raney nickel, palladium carbon, platinum oxide and the like. After the reaction, the target compound of the general formula (Va) can be isolated by filtering off the metal catalyst from the reaction mixture and distilling off the solvent under reduced pressure. Is obtained. The product may be pure enough as it is, but if necessary, purified by distillation or column chromatography to obtain a pure product.

(2) Reduction of phenylcyanopyridines with metal hydrides

(m-

NO tsT one (

(Vll) (Va) The phenylcyanoviridines (VIII) are reacted with a metal hydride at a temperature of 178 to 150 ° C, preferably 1 to 78 to 100 ° C, preferably using a solvent.

The solvent is not particularly limited as long as it does not directly participate in the reaction. Examples thereof include aromatic hydrocarbons such as benzene, toluene and xylene; ketones such as acetone, methyl ethyl ketone and methyl isobutyl ketone; chloroform, dichloromethane Halogenated hydrocarbons, such as methyl acetate, ethyl acetate, etc .; And polar solvents such as tetrahydrofuran, acetonitrile, dioxane, N, N-dimethylformamide, N-methylpyrrolidone, dimethylsulfoxide, pyridine and the like.

Examples of the metal hydride include sodium borohydride, lithium aluminum hydride and the like. After the reaction, the target compound of the general formula (Va) can be isolated by post-treating the remaining metal hydride and then distilling off the solvent under reduced pressure, and represented by the general formula (Va) A compound is obtained. The product may be sufficiently pure as it is, but if necessary, purified by distillation, column chromatography, or other means to obtain a pure product.

(3) Reduction of oximes

(In the above formula (IX), R ³ , RR ⁵ , m and n are as defined in the above general formula (I).)

Oximes (K) and hydrogen in the presence of a metal catalyst, aqueous ammonia, preferably in a solvent, from 0 to 100. C, preferably at 25-50 ° C. The solvent is not particularly limited as long as it does not directly participate in the reaction. For example, alcohols such as methanol, ethanol, and isopropanol; aromatic hydrocarbons such as benzene, toluene, and xylene; acetone, methylethyl Ketones such as ketone and methylisobutyl ketone; halogenated hydrocarbons such as chloroform and dichloromethane; water; esters such as methyl acetate and ethyl acetate; or tetrahydrofuran, lycetonitrile, dioxane, N, N-dimethylformamid And polar solvents such as N-methylpyrrolidone, dimethylsulfoxide and pyridine. Examples of the metal catalyst include Raney nickel, palladium carbon, platinum oxide and the like. After the reaction, the target compound of the general formula (V) can be isolated by filtering off the metal catalyst from the reaction mixture and then distilling off the solvent under reduced pressure. The compound represented by the general formula (V) A compound is obtained.

Phenylcyanopyridines (VIII) can be prepared by a known method, for example, the method described in Synthetic Communications, Vol. 11, page 513 (1981), by reacting the corresponding haloarenes and phenolic carboxylic acids with a transition metal catalyst and a base. By doing so, they can be synthesized.

The oximes (IX) can be synthesized by reacting the corresponding acetophenones with the corresponding hydroxysulfamines in the presence of carbonated lime by a known method.

The synthesis of furibiridyl methyl amic acid addition salt (X) can be carried out by the following method.

&

(In the above formulas (V) and (X), R ³ , RR ⁵ , m and n are as defined in the above general formula (I), and Y is an acid.)

The phenylpyridylmethylamines (V) and the acid are reacted, preferably in a solvent, at 15 to 50 ° C, preferably 0 to 25 ° C.

Organic acids and inorganic acids can be used as the acid.As the organic acids, acetic acid, propionic acid, butyric acid, oxalic acid, adipic acid, dodecandioic acid, lauric acid, stearic acid, trifluoroacetic acid, fumaric acid, maleic acid Carboxylic acids such as acid, benzoic acid and phthalic acid; methanesulfonic acid, 1,3-propanedisulfonic acid, p-toluene Examples thereof include sulfonic acids such as enesulfonic acid and dodecylbenzene sulfonic acid. Examples of the inorganic acid include hydrochloric acid, sulfuric acid, nitric acid, and carbonic acid. The solvent is not particularly limited as long as it does not directly participate in the reaction, and examples thereof include aromatic hydrocarbons such as benzene, toluene, and xylene; ketones such as acetone, methyl ethyl ketone, and methyl isobutyl ketone; chloroform, dichloromethane Water; esters such as ethyl acetate and methyl acetate; and polar solvents such as tetrahydrofuran, acetonitrile, dioxane, Ν, Ν-dimethylformamide, Ν-methylpyrrolidone, and dimethyl sulfoxide. be able to.

After the reaction, the solvent is distilled off under reduced pressure, and the crystals are separated by filtration to synthesize benzylamine inorganic acid salt and organic acid salt. This condition is sufficient, but if further purification is desired, high purity pyridylmethylamic acid adduct (X) can be synthesized by washing with the above-mentioned organic solvent.

The starting compound represented by the general formula (VI) can be synthesized by the following method.

(IV) (XI) (VI)

(In the above formula (XI), R ³ , R ⁴ , X, m and W are as defined in the above general formulas (1) and (VI).)

The carboxylic acid chlorides (IV) and the pyridylmethylamines (XI) can be prepared in the presence or absence of a base, preferably using a solvent, at a temperature of 10 to 50 ° C, preferably 0 to 25 ° C. Let react.

The solvent is not particularly limited as long as it does not directly participate in the reaction, and examples thereof include aromatic hydrocarbons such as benzene, toluene, and xylene; acetone, methylethyl Ketones such as norketone and methyl isobutyl ketone; halogenated hydrocarbons such as chloroform and dichloromethane; water; esters such as methyl acetate and ethyl acetate; or tetrahydrofuran, acetonitrile, dioxane, Ν, Ν-dimethylformamide, Ν — Polar solvents such as methylpyrrolidone, dimethylsulfoxide and pyridine.

Examples of the base include alkali metal hydrides such as sodium hydride; alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; alkali metal carbonates such as sodium carbonate and carbonated lithium; inorganic salts Amides such as pyridine and triethylamine;

After the reaction, in order to isolate the target compound of the general formula (VI), when a solvent soluble in water is used, the solvent is distilled off under reduced pressure, and water is added. Aromatic hydrocarbons such as benzene, toluene and xylene; halogenated hydrocarbons such as chloroform and dichloromethane; extracted with esters such as ethyl acetate, washed with water, dilute hydrochloric acid and, if necessary, saturated saline It may be dried with a drying agent such as anhydrous sodium sulfate or anhydrous magnesium sulfate, and the solvent may be distilled off under reduced pressure. If a water-insoluble solvent is used, water is added to the reaction mixture, and the mixture is separated.If necessary, the organic layer is washed with dilute hydrochloric acid or saturated saline, and then a desiccant such as anhydrous sodium sulfate or anhydrous magnesium sulfate is used. Then, the solvent may be distilled off under reduced pressure. If the residue obtained after distilling off the solvent is purified by recrystallization, suspension washing, column chromatography, etc., the compound represented by the general formula (VI) can be obtained. Compound (II) can be synthesized by the method described in JP-A-2-62876.

The compound represented by the general formula (I) has a high bactericidal effect against phytopathogenic fungi such as blast fungus, powdery mildew, rust fungus and mildew, and is an active ingredient of a fungicide for agricultural and horticultural use. Useful as In addition, the compounds of the present invention may be used in the form of insects such as brown planthopper, brown beetle, brown beetle, etc., white-spotted plants such as black-tailed leafhopper and white-spotted pie, and aphids such as aphids such as red-spotted moss. , Lepidoptera such as Pleurotus japonicus, P. conch; Coleoptera such as mosquitoes; dipterans such as housefly, Aedes aegypti, and akaye abilities; insects of the order Orthoptera; and high control activity against eggs and larvae of the order Acephalidaceae such as Nami-nada, Nisenamihada and Ran. It is also useful as an active ingredient for agricultural and horticultural insecticides and pesticides. However, the phytopathogenic fungi, insects and mites to be controlled by the compound of the present invention are not limited to those exemplified above. When the compound represented by the general formula (I) is used as a fungicide, an insecticide, and / or an acaricide for agricultural and horticultural use, it may be used alone, but preferably used in the art. Used as agricultural and horticultural fungicides, insecticides, and Z or acaricides in the form of compositions made with the used pesticide adjuvants. These forms are not particularly limited, but are preferably in the form of emulsions, wettable powders, powders, flowables, fine granules, granules, tablets, oils, sprays, aerosols and the like. One or more compounds represented by the general formula (I) can be blended as an active ingredient.

Pesticide adjuvants used to produce the above agricultural and horticultural fungicides, insecticides, and / or acaricides include, for example, agricultural and horticultural fungicides, insecticides, and Z or acaricides. It can be used for the purpose of improving the effect, stabilizing, and improving the dispersibility. Examples of pesticidal auxiliaries include carriers (diluents), spreading agents, emulsifiers, wetting agents, dispersants, disintegrants, and the like.

Examples of the liquid carrier include water, aromatic hydrocarbons such as toluene and xylene, alcohols such as methanol, butanol and daricol, ketones such as acetone, amides such as dimethylformamide, sulfoxides such as dimethyl sulfoxide, and methyl. Examples include naphthalene, cyclohexane, animal and vegetable oils, and fatty acids. Examples of the solid carrier include clay, kaolin, talc, diatomaceous earth, silica, calcium carbonate, montmorillonite, bentonite, feldspar, quartz, alumina, sawdust, nitrocellulose, starch, gum arabic and the like. Usable surfactants can be used as emulsifiers and dispersants, such as higher alcohols such as sodium sulfate, stearyltrimethylammonium chloride, polyoxyethylene alkylphenyl ether and lauryl betaine. An ionic surfactant, a cationic surfactant, a nonionic surfactant, an amphoteric ion surfactant or the like can be used. A spreading agent such as polyoxyethylene phenol ether; polyoxyethylene radial phenyl ether; a wetting agent such as dialkyl sulfosuccinate; a fixing agent such as carboxymethyl cellulose and polyvinyl alcohol; lignin sulfonic acid Disintegrants such as sodium and sodium lauryl sulfate can be used.

The content of the effective ingredient in the agricultural and horticultural fungicide, insecticide, and / or acaricide of the present invention is selected from the range of 0.1 to 99.5%, and various conditions such as a formulation form, an application method and the like are used. For example, about 0.5 to 20% by weight, preferably 1 to 10% by weight for powder, about 1 to 90% by weight, preferably 10 to 80% by weight for wettable powder, emulsion It is preferred that the preparations contain about 1 to 90% by weight, preferably 10 to 40% by weight, of the active ingredient.

For example, in the case of an emulsion, an emulsion of a stock solution can be prepared by mixing a solvent and a surfactant with the above-mentioned compound as an active ingredient. It can be applied after dilution. In the case of wettable powders, it is possible to prepare a stock solution by mixing the above active compound, a solid carrier, a surfactant and the like, and then dilute this stock solution to a predetermined concentration with water before use. it can. In the case of powder, the compound of the active ingredient, the solid carrier and the like can be mixed and applied as it is, and in the case of granules, the compound of the active ingredient, the solid carrier and a surfactant can be mixed and used. It can be manufactured by granulation and applied as it is. However, the production method of each of the above-mentioned preparation forms is not limited to the above-mentioned method, 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 fungicides, insecticides, and / or miticides of the present invention include, in addition to the compound of the present invention, an active ingredient, other fungicides, insecticides, acaricides, herbicides, insect growth regulators. Any active ingredient such as fertilizer, soil conditioner, etc. may be added. The method for applying the agricultural and horticultural fungicide, the insecticide, and / or the acaricide of the present invention is not particularly limited. It can be applied by any method such as foliage application, water application, soil treatment, and seed treatment. For example, in the case of foliar application, a solution having a concentration range of 5 to 1000 ppm, preferably 10 to 500 ppm can be used at an application rate of about 100 to 200 liters per 10 ares. For surface application, 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 is Rukoto used in solution application rate of about 1 to 10 per liter 1 m ² the concentration range of. 5 to 1000 ppm. In the case of seed treatment, about 10 to 100 ml of a solution in a concentration range of 10 to 1000 ppm per 1 kg of seed weight can be applied.

Hereinafter, the present invention will be described more specifically with reference to Examples, Production Examples, and Test Examples, but the scope of the present invention is not limited to the following. Example 1

Synthesis of 3-ethyl-11-methyl-1-N- [6- (4-trifluoromethoxyphenyl) -1-pyridylmethyl] pyrazole_5-carboxamide:

After cooling a mixture of 6- (4-trifluoromethoxyphenyl) -1-pyridylmethylamine (5.00 _g ), triethylamine (5 ml) and dichloromethane (50 ml) to 0-4 ° C, the mixture was cooled to 1-methyl-3 A solution of ethylvillazol-5-carboxylic acid chloride (3.21 _g ) in toluene (20 ml) was added, and the mixture was stirred for 30 minutes. The reaction mixture was poured into water (50 ml) and extracted with ethyl acetate. The organic layer was washed with dilute hydrochloric acid and saturated saline, and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography 1 to obtain 6.32 g of compound No. 4 shown in Table 11. Melting point was 120-121 ° C. Example 2

Synthesis of I, 3-dimethyl-1-N— [6- (4-trifluoromethoxyphenyl) -1-pyridylmethyl] pyrazole-5-carboxamide:

Under a nitrogen stream N- (6-chloro-2-pyridylmethyl) -1,3-dimethylvirazole-15-carboxamide (9.00 g), 4-trifluoromethoxybenzeneboronic acid (10.5 g), toluene (100 ml), dioxane (50 ml), a mixture of 2M sodium carbonate aqueous solution (50 ml) and water (25 ml) was heated to 70 ° C, and then tetrakistriphenylphosphine palladium (3.93 g) Was added and the mixture was stirred under reflux for 2 hours. Water (100 ml) was added to the reaction mixture, and extracted with ethyl acetate. The organic layer was washed with aqueous sodium bicarbonate and saturated saline, and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography to obtain Compound No. 31 described in Table 1

II. 8 g were obtained. Melting point was 123-124 ° C. Example 3

1,3-Dimethinole N- [6- (4-Trifluoromethoxy-nore) -2-pyridinolemethyl] pyrazole- Synthesis of 5_carboxamide hydrochloride:

1,3-Dimethyl N— [6- (4-trifluoromethoxyphenyl) -1-pyridylmethyl] pyrazole-5-carboxamide (0.5 g) in methanol (10 ml) solution 12N hydrochloric acid (1 ml) Was added and stirred at room temperature for 2 hours. The solvent was distilled off under reduced pressure, and the crystals were washed with methanol to obtain 0.35 _g of compound No. 60 shown in Table 12. The melting point was 208-209 ° C (decomposition).

The compounds described in Tables 1 and 2 were synthesized according to the methods of Examples 1 to 3. DO

Table 1 (continued)

i- (continued)

Table 1 (continued)

1 (continued)

i-1 (continued)

1 (continued)

Example 4

Synthesis of 6- (4-trifluoromethyloxyphenyl) -1-pyridylmethylamine: In a hydrogen atmosphere, 3-cyano 6- (4-trifluoromethylphenyl) pyridin (10 g), Raney nickel R-100 (10 g) And 28% aqueous ammonia (10 ml) were shaken at 50 ° C for 3 hours. After cooling to room temperature, Raney nickel was separated by filtration and the solvent was distilled off under reduced pressure to obtain 9.73 _g of compound No. 65 shown in Table 13.

Compound No. 68 was synthesized in the same manner. Example 5

Synthesis of 6- (4-trifluoromethoxyl) -1-3-pyridylmethylamine hydrochloride:

To a solution of 6- (4-trifluoromethoxyphenyl) -1-pyridylmethylamine (9.25 g) in methanol (50 ml) was added 12N hydrochloric acid (6 ml), and the mixture was stirred at room temperature for 2 hours. The solvent was distilled off under reduced pressure, and the crystals were washed with methanol to obtain 9.35 g of Compound No. 66 shown in Table 3. Melting point was 120-125 ° C.

The compounds shown in Table 3 were synthesized according to the methods of Examples 4 and 5.

1) ¾NMR (CDCI3) δ ppm: 3.96 (2H, s), 7.31 (2H, d), 7.69 (1H, d), 7.77 (1H, dd), 8.02 (2H , d), 8.63 (1H, d)

_{2) ¾NMR (CDC1 3) δ} ppm: 4. 05 (2H, s), 7. 33 (2H, d), 7. 38 (1H, d), 7. 59 (2H, dd), 7. 82 ( 1H, dd), 8.77 (1H, d) Formulation example 1

Wettable powder:

20 parts by weight of the compound of the present invention, Carplex # 80 (white carbon, Shionogi & Co., Ltd., trade name) 20 parts by weight, ST kaolin clay (Riki Orinite, Tsuchiya Kaolin Co., Ltd., trade name) 52 parts by weight, Solpol 9047K (Anionic surfactant, Toho Chemical Co., Ltd., 5 parts by weight), Lunox P65L (Anionic surfactant, Toho Chemical Co., Ltd., 3 parts by weight) A wettable powder of 20% by weight of the active ingredient was obtained. 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), and 5 parts by weight of Kalex Plex # 80 (white carbon, Shionogi & Co., Ltd., trade name) Pulverized to produce a powder containing 2% by weight of active ingredient.

Emulsion:

20 parts by weight of the compound of the present invention are dissolved in a mixed solvent consisting of 35 parts by weight of xylene and 30 parts by weight of dimethylformamide, and dissolved in Solpol 3005X (a mixture of a nonionic surfactant and an anionic surfactant, Toho 15 parts by weight were added to obtain an emulsion containing 20% by weight of the active ingredient. Formulation Example 4

Flowable:

30 parts by weight of the compound of the present invention, 5 parts by weight of Sorbol 9047K, 3 parts by weight of Sorbone T-20 (nonionic surfactant, trade name of Toho Chemical Co., Ltd.), 8 parts by weight of ethylene glycol water 44 Parts by weight were wet-pulverized with a Dynomill (manufactured by Shinmaru Enterprises), and 10 parts by weight of a 1% by weight aqueous solution of xanthan gum (natural polymer) was added to the slurry-like mixture. An absurd lj was obtained.

Test example 1

Bactericidal effect on wheat powdery mildew:

The compound (III) disclosed in the above-mentioned JP-A-64-62876 and each of the compounds of the present invention were prepared in the same manner as in Preparation Example 3, and the preparation was diluted to a predetermined concentration with water. The foliage was sprayed at a rate of 10 ml per pot to 1-2-wheat wheat (cultivar: Norin 61) grown in 6 cm pots. After air-drying with chemicals, spray inoculation with a spore suspension obtained from wheat leaves infected with wheat powdery mildew (Erysophe graminis), and then inoculate in a greenhouse? Left for ~ 10 days.

For evaluation, various diseased area ratios were evaluated, and the control value was calculated from the following formula. The results are shown in Table 4 (in the table below, the compound numbers correspond to Nos. In Tables 1 and 2). As a comparative compound, the compound (III) in which R ⁵ in the general formula (I) is an alkyl group is shown.

{(Average disease area ratio in untreated area) — (Average disease rate in treated area)} χ 100 Control value):

(Average disease area ratio of untreated area) Table 1 4

Compound 濃度 concentration pm) Control value (%)

1 500 1 00

2 500 1 00

3 500 1 00

4 500 1 00

5 500 1 00

6 500 100

7 500 1 00

1 1 500 1 00

1 2 500 1 00

1 3 500 1 00

14 500 1 00

1 5 500 1 00

1 7 500 1 00

1 8 500 1 00

1 9 500 .1 00

23 500 1 00

24 500 1 00

25 500 1 00

27 500 1 00

30 500 1 00

31 500 100

34 500 100

36 500 100

37 500 100

38 500 1 00

Table 4 (continued)

Test example 2

Bactericidal effect against wheat leaf spot disease:

Each of the compounds of the present invention prepared in the same manner as in Preparation Example 3 was diluted to a predetermined concentration with water, and seedlings were grown in pots of 6 cm in diameter at the 1-2 leaf stage (cultivar: Norin 61 ) Was sprayed with foliage at a rate of 10 ml per pot. After air-drying with chemicals, spraying and spraying a spore suspension obtained by grinding wheat leaves infected with wheat leaf rot (Puccinia recondit), keeping in a wet room at 22 ° C for 15 hours, Left in the bath for 7 days.

For evaluation, various diseased area ratios were evaluated, and the control value was calculated in the same manner as in Test Example 1 above. The results are shown in Table 1-5 (in the table below, the compound numbers correspond to the numbers in Tables 1 and 2).

Table 1 5

Compound Να ¾i undesired (nnm) control "(ffi (%)

1 1 2 5 1 0 0

3 1 2 5 1 0 0

4 125 100

6 1 25 100

11 125 100

1 2 1 2 5 1 0 0

10 Ω

1 0 0

o i on

1 Q i on

23 125 100

2 4 1 2 5 1 0 0

2 7 1 2 5 1 Q 0

3 i 125 100

34 125 100

36 125 100

37 125 100

38 125 100

40 125 100

41 125 100

58 125 100

59 1.25 100

60 125 100

61 125 100

62 125 100

63 125, 100 Test example 3

Insecticidal effect of Lotus leafworm:

Cabbage cut leaves (6 cm in diameter) were immersed in a water dilution of the insecticide of the present invention (wettable powder) produced according to the formulation of Formulation Example 1 for the compound of the present invention for 1 minute. After immersion, it was air-dried and placed in a plastic cup (7 cm in inside diameter). Five 3rd-stage insects of Lotus spruce were released into this cup (1 concentration, 2 repetitions). The larvae were kept in a constant temperature room at 25 ° C, and after 5 days from the release, the larvae were examined for viability and agony. The results are shown in Table 6 (in the table below, the compound numbers correspond to Nos in Table 11).

Table 1 6

Test example 4

Acaricidal effect on adult of Nami-nada:

The stems of the kidney seedlings, each of which had one primary leaf, were inserted into a test tube (volume: 50 ml) filled with water, and 15 female adults of Nami-nada were inoculated per leaf. One day after the inoculation, the miticide was prepared according to the formulation of Formulation Example 3 by using the compound (III) disclosed in Japanese Patent Application Laid-Open No. Sho 62-62876 and the various lignin compounds of the present invention, respectively, on the leaf with the spider mites. (Emulsion) was immersed (about 5 seconds) in water dilution (1 concentration, 2 repetitions). The plants were kept in a constant temperature room at 25 ° C, and on the 5th day after the treatment, the number of adult female nymphs on the green leaves was examined, and the adult kill ratio (%) was calculated based on the results. The results are shown in Table 7 (in the table below, the compound numbers correspond to Nos. In Tables 1 and 2). table-

Although the present invention has been described in detail and with reference to specific embodiments, it will be apparent to those skilled in the art that various changes and modifications can be made without departing from the spirit and scope of the invention.

This application is based on Japanese Patent Application No. 2002-11966 filed on January 21, 2002 and Japanese Patent Application No. 2002-281980 filed on September 26, 2002, the contents of which are hereby incorporated by reference. It is captured. Industrial applicability

The pyrazolecarboxamides of the present invention have an excellent control effect against bacterial strains, harmful insects and mites, and are excellent insecticides and acaricides for agriculture, forestry and epidemics. In addition, it is expected to be used as a pesticide for livestock, fisheries, and various kinds of pests in preservation and public health of various products.

Claims

The scope of the claims

1. A pyrazolecarboxamide compound represented by the following general formula (I) or an acid addition salt thereof:

In the formula, R ¹ represents an alkyl group of Ci Cg,

R ² represents an alkyl group of Ci Cs, a haloalkyl group of C! Cs or an alkoxy group of Ci Cs,

R ³ represents a hydrogen atom or an alkyl group of ~ C ₃ ,

R ⁴ represents an alkyl group of Ci Cg, a haloalkyl group of Ci Cs or a halogen atom, provided that when m is 2 or more, R ⁴ may be the same or different;

R ⁵ represents an alkyl group, a haloalkyl group, an alkoxy group, an alkoxyalkoxy group, a haloalkoxy group, a hydroxyl group, an acyloxy group, a halopropyloxy group, an alkylthio group, a formyl group,

R ⁶

~~ ^ group represented by (wherein, R ⁶ and R ⁷ may be the same or different, their respective represents a hydrogen atom or a ^ ~ ^ alkyl group) in -OR ^7, or two adjacent Do, but they join together

'-. ⁰ _F ^FF or

When n is 1, R ⁵ is not an alkyl group, and when n is 2 or more, R ⁵ may be the same or different;

m represents an integer of 0 to 3,

n represents an integer of 1 to 5,

p represents 0 or 1,

X represents a hydrogen atom, a C ₃ -C ₃ alkyl group, an alkoxy group or a halogen atom.

2. The pyrazolecarboxamide compound or an acid addition salt thereof according to claim ^{1, wherein} R ¹ is a methyl group.

3. The pyrazole carboxamide compound or an acid addition salt thereof according to claim 1, wherein R ² is a methyl group or an ethyl group.

4. pyrazole carboxamide Mi de compound or an acid addition salt thereof according to any one of the range 1 to 3 according to R ⁵ is a haloalkoxy group a haloalkyl group or a C ₁ -C ₅ a C i Cg.

5. The pyrazole carboxamide compound or an acid addition salt thereof according to any one of claims 1 to 4, wherein R ³ is a hydrogen atom.

6. The pyrazole carboxamide compound or an acid addition salt thereof according to any one of claims 1 to 5, wherein X is a hydrogen atom.

7. The pyrazolecarboxamide compound or an acid addition salt thereof according to any one of claims 1 to 6, wherein m is an integer of 0 to 2, and n is 1 or 2.

8. A phenylpyridylmethylamine compound represented by the following general formula (II) or an acid addition salt thereof:

Wherein R ³ , R ⁴ and m are as defined in the general formula (I) described in Claim 1;

R ⁸ represents a haloanorecoxy group.

9. A composition comprising the pyrazolecarboxamide compound or the acid addition salt thereof according to any one of claims 1 to 7, and a pesticide adjuvant.

10. Use of the pyrazolecarboxamide compound or the acid addition salt thereof according to any one of claims 1 to 7 as a pesticide.

11. Use according to claim 10, wherein the pesticide is a fungicide, insecticide or acaricide.

12. A method for controlling pests, which comprises contacting a pest with an effective amount of the pyrazolecarboxamide compound or an acid addition salt thereof according to any one of claims 1 to 7.

13. The method according to claim 12, wherein the pest is a fungus, an insect, or a mite.