JPH0789937A - Phenoxyalkylamine derivative, production thereof and pest-controlling agent for agricultural and horticultural purposes - Google Patents

Abstract

PURPOSE:To obtain a novel compound which is useful as an active ingredient for pest-controlling agent such as insecticide, acaricide or fungicide for agricultural and horticultural purposes. CONSTITUTION:A compound of the formula I [R<1> is 1-4 C alkyl, H; R<2> is 1-6 C alkyl, 3-8 C cycloalkyl, 1-4 C haloalkyl ; R<3> is R<1>, halogen; R<4> is A<2>-O-R<6> (A<2> is 1-4 C alkylene, R<6> is 1-4 C alkyl, 3-5 C alkenyl, 3-5 C alkinyl), H, 1-12 C alkyl, halogen, 3-5 C alkenyl; R<5> is the above-mentioned group except the cases where R<2> is 1-6 C alkyl, R<4> is 6-12 C alkyl and A<1> is 2 to 5 C alkylene, for example, N-{2-[4--(2-methoxyethyl)-2-methylphenoxy]ethyl}-3-t-butyl-1- methyl-5-pyrazole-carboxamide. Said compound is obtained by reaction of a pyrazole-carboxylic acid derivative of the containing II [X is halogen, R<7>O (R<7> is 1-6 C alkyl), OH] with a phenoxyalkylamine of the formula III.

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a novel phenoxyalkylamine derivative which is a pesticide for agricultural and horticultural use which is useful as an insecticide, acaricide, fungicide and the like.

[0002]

Description of the Prior Art As a phenoxyalkylamine derivative, the following formula (1 ') is described in JP-A-3-27360:

[0003]

[Chemical 4]

[Wherein R ¹ 'represents an alkyl group having 1 to 5 carbon atoms or a hydrogen atom; R ² ' represents an alkyl group having 1 to 5 carbon atoms; R ³ 'is 1 to 1 carbon atoms. Represents 5 alkyl groups, hydrogen atoms or halogen atoms; R ⁴ 'is A ² ' -OR ⁶ '
(Note that A ² 'represents an alkylene group having 1 to 5 carbon atoms,
R ⁶ 'represents an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 3 to 5 carbon atoms or an alkynyl group having 3 to 5 carbon atoms. ), A hydrogen atom, an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 3 to 5 carbon atoms; R ⁵ 'represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms or a halogen atom; ¹ 'is a 2 to 5 alkylene groups having a carbon. ] The pyrazole derivative shown by these is disclosed.

However, no report has been made on a novel 5-pyrazolecarboxamide derivative in which the 4-position of the pyrazole ring is unsubstituted as in the present invention. Therefore, since the phenoxyalkylamine derivative of the present invention is a novel compound, it is not known that it has a pesticidal activity for agricultural and horticultural use which is useful as an insecticide, acaricide or fungicide.

[0006]

DISCLOSURE OF THE INVENTION The object of the present invention is to provide a novel phenoxyalkylamine derivative, a process for producing the same, and agricultural and horticultural pests useful as insecticides, acaricides, fungicides containing the same as active ingredients. It is to provide a control agent.

[0007]

Means for Solving the Problems As a result of studies to solve the above problems, the present inventors have found that a novel phenoxyalkylamine derivative is useful as an insecticide, acaricide, fungicide, etc. for agricultural and horticultural use. It was found that the pest control agent of the present invention has a remarkable control activity, and completed the present invention. That is, the present invention is as follows. The first invention is represented by the following formula (1):

[0008]

[Chemical 5]

[Wherein R ¹ represents an alkyl group having 1 to 4 carbon atoms or a hydrogen atom; R ² is an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms or a carbon atom] Number 1
~ 4 haloalkyl groups; R ³ represents an alkyl group having 1 to 4 carbon atoms, a hydrogen atom or a halogen atom; R ⁴
Is A ² —O—R ⁶ (wherein A ² represents an alkylene group having 1 to 4 carbon atoms, R ⁶ is an alkyl group having 1 to 4 carbon atoms,
It represents an alkenyl group having 3 to 5 carbon atoms or an alkynyl group having 3 to 5 carbon atoms. ), Hydrogen atom, carbon number 1-12
Represents an alkyl group, a halogen atom or an alkenyl group having 3 to 5 carbon atoms; R ⁵ represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms or a halogen atom; A ¹ represents ^{1 to 1} carbon atom
Represents 5 alkylene groups. However, R ¹ has 1 to ¹ carbon atoms.
Represents 4 alkyl groups or hydrogen atoms; R ² has 1 carbon atom
It represents a 6 alkyl group; R ³ represents a number 1-5 alkyl group, a hydrogen atom or a halogen atom carbon; R ⁴ is A
^2- OR ⁶ (wherein A ² represents an alkylene group having 1 to 4 carbon atoms, R ⁶ represents an alkyl group having 1 to 4 carbon atoms, an alkenyl group having 3 to 5 carbon atoms or 3 carbon atoms). ~ 5 alkynyl groups), a hydrogen atom, an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 3 to 5 carbon atoms; R
⁵ represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms or a halogen atom; A ¹ excludes an alkylene group having 2 to 5 carbon atoms. ] It is related with the phenoxy alkylamine derivative shown by these. The second invention is the following formula (2):

[0010]

[Chemical 6]

[Wherein R ¹ and R ² have the same meanings as defined above; X is a halogen atom, R ⁷ O group (wherein R ⁷ represents an alkyl group having 1 to 6 carbon atoms) or a hydroxyl group. Represent ]
And a pyrazolecarboxylic acid derivative represented by the following formula (3):

[0012]

[Chemical 7]

## STR3 ## wherein R ³ , R ⁴ , R ⁵ and A ¹ have the same meanings as defined above, and phenoxyalkylamines represented by the above formula (1) are used. The present invention relates to a method for producing a phenoxyalkylamine derivative.

A third invention relates to a pesticide for agricultural and horticultural use, which contains the phenoxyalkylamine derivative represented by the formula (1) described in the first invention as an active ingredient.

The present invention will be described in detail below. R ^{1 to} R ⁷ , A ¹ , A ² and X in the novel phenoxyalkylamine derivative (1) which is the above-mentioned target compound and the compounds (2) and (3) which are raw materials for producing the same are as follows.

Examples of R ¹ include an alkyl group having 1 to 4 carbon atoms and a hydrogen atom. R ¹
Examples of the alkyl group in are linear or branched ones (methyl group, ethyl group, n-propyl group, i-
Propyl group, n-butyl group, i-butyl group, t-butyl group, etc.); preferably those having 1 to 2 carbon atoms; and more preferably methyl group.

Examples of R ² include an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, and a haloalkyl group having 1 to 4 carbon atoms. Examples of the alkyl group for R ² include linear or branched ones; preferably one having 1 to 4 carbon atoms; more preferably one having 3 or 4 carbon atoms. Those (n-propyl group, i-propyl group, t-butyl group, i-butyl group, etc.) are preferable.

The cycloalkyl group for R ² is
It preferably has 3 to 6 carbon atoms; more preferably a cyclopropyl group. Examples of the halogen atom of the haloalkyl group for R ² include a chlorine atom, an iodine atom, a bromine atom, a fluorine atom and the like; preferably a fluorine atom. Examples of the alkyl group of the haloalkyl group for R ² include linear or branched ones; preferably those having 1 to 4 carbon atoms; and more preferably methyl group. The most preferred haloalkyl group for R ² is a trifluoromethyl group.

Examples of R ³ include an alkyl group having 1 to 4 carbon atoms, a hydrogen atom and a halogen atom. Examples of the alkyl group in R ³ include, for example,
Examples thereof include linear or branched ones; preferably a methyl group. Examples of the halogen atom for R ³ include a chlorine atom, an iodine atom, a bromine atom, a fluorine atom and the like; preferably a chlorine atom.

R ⁴ is, for example, A ² --O--R
⁶ (Note that A ² represents an alkylene group having 1 to 4 carbon atoms, R ⁶ represents an alkyl group having 1 to 4 carbon atoms, and 3 to 5 carbon atoms.
Represents an alkenyl group or an alkynyl group having 3 to 5 carbon atoms. ), A hydrogen atom, an alkyl group having 1 to 12 carbon atoms, a halogen atom, an alkenyl group having 3 to 5 carbon atoms, and the like.

Examples of A ² in A ² -O-R ⁶ of R ⁴ include linear or branched ones; preferably, those having 1 or 2 carbon atoms are preferable; Ethylene groups are preferred. R ⁴ A ² -OR
Examples of the alkyl group of R ⁶ in ⁶ include linear or branched ones; preferably those having 1 to 3 carbon atoms; and more preferably methyl group and ethyl group. Good.

[0022] The alkenyl group of R ⁶ in A ² -O-R ⁶ in R ^4, for example, there may be mentioned a straight or branched; preferably from allyl group. R
The alkynyl group R ⁶ in A ² -O-R ⁶ of ^4, for example, there may be mentioned a straight or branched; preferably from 1-propynyl group. And
The most preferable examples of A ² —O—R ⁶ include a 2-methoxyethyl group, a 2-ethoxyethyl group, a 2-propoxyethyl group and a 2-propargyloxyethyl group.

Examples of the alkyl group having 1 to 12 carbon atoms in R ⁴ include linear or branched ones; preferably those having 1 to 10 carbon atoms; Preferably, it has 1 to 6 carbon atoms. Examples of the halogen atom in R ⁴ include a chlorine atom, an iodine atom, a bromine atom, a fluorine atom and the like; preferably a chlorine atom. Examples of the alkenyl group having 3 to 5 carbon atoms in R ⁴ include, for example,
Examples thereof include linear or branched ones; preferably 1-propynyl group.

Examples of R ⁵ include a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, and a halogen atom. Examples of the alkyl group for R ⁵ include, for example,
Examples thereof include linear or branched ones; preferably those having 1 or 2 carbon atoms; and more preferably methyl group. The substitution position of R ⁵ is not particularly limited; preferably 3-position and 6-position.

Examples of the halogen atom for R ⁵ include a chlorine atom, an iodine atom, a bromine atom and a fluorine atom; preferably a chlorine atom.
Examples of the alkylene group for A ¹ include linear or branched ones; preferably those having 2 to 4 carbon atoms; and more preferably ethylene groups. Examples of X include a halogen atom and R ⁷ O.
Examples thereof include a group (in which R ⁷ represents an alkyl group having 1 to 6 carbon atoms).

Examples of the halogen atom in X include a chlorine atom, an iodine atom, a bromine atom, a fluorine atom and the like; preferably a chlorine atom.
Examples of the alkyl group for R ⁷ include linear or branched ones, and preferably a methyl group or an ethyl group.

The compound (1) may be any of the above-mentioned various substitutions.
A combination of groups [however, R ¹Has 1 to 4 carbon atoms
Represents an alkyl group or a hydrogen atom of R;²Has 1 to 6 carbon atoms
Represents one alkyl group; R³Is an alky having 1 to 5 carbon atoms
Represents a hydrogen atom or a halogen atom; R^FourIs A²−
OR⁶(In addition, A²Is an alkylene group having 1 to 4 carbon atoms
Represents R⁶Is an alkyl group having 1 to 4 carbon atoms, 3 carbon atoms
~ 5 alkenyl groups or C 3 -C 5 alkyls
Represents a nyl group. ), A hydrogen atom, an alkyl having 1 to 5 carbon atoms
Represents an alkyl group or an alkenyl group having 3 to 5 carbon atoms; R^FiveIs
Hydrogen atom, alkyl group having 1 to 4 carbon atoms or halogen atom
Represents a child; A¹Represents an alkylene group having 2 to 5 carbon atoms
Excluding cases. ] Can be mentioned.

Among them, the preferable ones from the viewpoint of medicinal effect are as follows. (a) R ¹ is an alkyl group having 1 to 4 carbon atoms, R ² is an alkyl group having 1 to 6 carbon atoms, and R ³ is 1 to 1 carbon atoms.
4 alkyl groups, R ⁴ is (CH ₂ ) ₂ —O—
A (alkyl group having 1 to 4 carbon atoms), R ⁵ is a hydrogen atom, A ¹ is (CH _{2) 2,} compound. (b) R ¹ is an alkyl group having 1 to 4 carbon atoms, R ² is an alkyl group having 1 to 6 carbon atoms, and R ³ is 1 to 1 carbon atoms.
4 alkyl groups, R ⁴ is (CH ₂ ) ₂ —O—
A (alkyl group having 1 to 4 carbon atoms), R ⁵ is an alkyl group having 1 to 4 carbon atoms, A ¹ is (CH _{2) 2,} compound.

(C) R ¹ is an alkyl group having 1 to 4 carbon atoms, R ² is a cycloalkyl group having 3 to 8 carbon atoms, and R ³ is an alkyl group having 1 to 4 carbon atoms. And a compound in which R ⁴ is (CH ₂ ) ₂ —O— (alkyl group having 1 to 4 carbon atoms), R ⁵ is a hydrogen atom, and A ¹ is (CH ₂ ) ₂ . (d) R ¹ is an alkyl group having 1 to 4 carbon atoms, R ² is a haloalkyl group having 1 to 4 carbon atoms, R ³ is an alkyl group having 1 to 4 carbon atoms, and R ⁴ There (CH _{2) 2} -O
- a (alkyl group having 1 to 4 carbon atoms), R ⁵ is a hydrogen atom, A ¹ is (CH _{2) 2,} compound.

(E) R ¹ is an alkyl group having 1 to 4 carbon atoms, R ² is an alkyl group having 1 to 6 carbon atoms, and R ³
Is an alkyl group having 1 to 4 carbon atoms, and R ⁴ is (C
H ₂ ) ₂ —O— (alkenyl group having 3 to 5 carbon atoms), R ⁵ is a hydrogen atom, and A ¹ is (CH ₂ ) ₂ . (f) R ¹ is an alkyl group having 1 to 4 carbon atoms, R ² is an alkyl group having 1 to 6 carbon atoms, and R ³ is 1 to 1 carbon atoms.
4 alkyl groups, R ⁴ is (CH ₂ ) ₂ —O—
(C3-5 alkenyl group), R ⁵ is a hydrogen atom, and A ¹ is (CH ₂ ) ₂ .

(G) R ¹ is an alkyl group having 1 to 4 carbon atoms, R ² is an alkyl group having 1 to 6 carbon atoms, and R ³
Is an alkyl group having 1 to 4 carbon atoms, and R ⁴ is 1 carbon atom
~ 12 alkyl groups, R ⁵ is a hydrogen atom,
A compound in which A ¹ is (CH ₂ ) ₂ . (h) R ¹ is an alkyl group having 1 to 4 carbon atoms, R ² is an alkyl group having 1 to 6 carbon atoms, R ³ is a hydrogen atom, and R ⁴ is 3 to 5 carbon atoms. Is an alkenyl group of R
A compound in which ⁵ is a hydrogen atom and A ¹ is (CH ₂ ) ₂ .

R ^{1 of} these compounds represented by (a) to (h)
Examples of R ⁴ to R ⁴ include the preferable ones and the more preferable ones shown in the description of R ^{1 to} R ⁴ . Specific compounds (1) among these compounds include compounds 1 to 4 and 8 described in Tables 1 to 5 below.
15,17-19,21-23,26,30,34 can be mentioned.

The compound (1) of the present invention can be synthesized by reacting the compound (2) with the compound (3) in a solvent or without a solvent, as shown below; Is preferably reacted in the presence of a base when X is a halogen atom in order to accelerate the reaction;
When X is an R ⁷ O group, the reaction is preferably performed in the presence of a base catalyst; when X is a hydroxyl group, the reaction is preferably performed in the presence of a dehydrating agent.

[0034]

[Chemical 8]

(Wherein R ¹ , R ² , R ³ , R ⁴ , R ⁵ ,
A ¹ and X are as defined above. ) The solvent when X is a halogen atom is not particularly limited as long as it does not directly participate in the reaction, and examples thereof include benzene, toluene,
Chlorinated or non-chlorinated aromatics such as xylene, methylnaphthalene, petroleum ether, ligroin, hexane, chlorobenzene, dichlorobenzene, methylene chloride, chloroform, dichloroethane, trichloroethylene, cyclohexane, aliphatic, alicyclic Hydrocarbons; ethers such as diethyl ether, tetrahydrofuran, dioxane; ketones such as acetone, methyl ethyl ketone; N, N-dimethylformamide,
Amides such as N, N-dimethylacetamide;
Organic bases such as triethylamine, pyridine, N, N-dimethylaniline and the like; 1,3-dimethyl-2-imidazolidinone; dimethylsulfoxide; mixtures of the above solvents and the like.

The amount of the solvent used may be such that the concentration of the compound (2) is in the concentration range of 2 to 80% by weight, preferably the compound (2).
It is preferable to use it so that the concentration thereof is 5 to 70% by weight. The base is not particularly limited, and examples thereof include triethylamine, pyridine, N, N-dimethylaniline, D
Organic bases such as BU; alkali metal alkoxides such as sodium methoxide and sodium ethoxide; sodium hydride, sodium amide, sodium hydroxide, potassium hydroxide, sodium carbonate, sodium hydrogen carbonate,
Mention may be made of inorganic bases such as potassium carbonate;
Organic bases are preferred.

The amount of the base used can be 0.001 to 5 times by mole with respect to the compound (2), and preferably 1.0 to 1.5 times by mole. . The reaction temperature is not particularly limited, but is within a temperature range from the ice-cooling temperature to the boiling point of the solvent to be used, 0-30
C is preferred. The reaction time varies depending on the above-mentioned concentration and temperature, but is usually 0.3 to 2 hours.
The amount of the raw material compound used is 0.5 to 2 times mol of the compound (3) with respect to the compound (2), but preferably 1.0.
It is preferably about 1.5 times the molar amount.

When X is an R ⁷ O group, the solvent may be methanol, in addition to the solvent shown when X is a halogen atom.
Alcohols such as ethanol, propanol, butanol; and mixtures of these solvents can be mentioned. The amount of the solvent used is the same as that of the compound (3).
The compound (3) can be used in a concentration range of 2 to 80% by weight, but the compound (3) is preferably used in a concentration of 5 to 70% by weight.

The base catalyst is not particularly limited, and examples thereof include organic bases such as triethylamine, pyridine, N, N-dimethylaniline and DBU; alkali metal alkoxides such as sodium methoxide and sodium ethoxide; sodium hydride and sodium. Mention may be made of inorganic bases such as amides, sodium hydroxide, potassium hydroxide, sodium carbonate, sodium hydrogen carbonate, potassium carbonate; alkali metal alkoxides are preferred.

The amount of the base used can be 0.001 to 5 times by mole with respect to the compound (3), but preferably 0.1 to 1.5 times by mole. . The reaction temperature is not particularly limited, but is within a temperature range from the ice-cooling temperature to the boiling point of the solvent to be used, 50 to 1
10 ° C is preferred. The reaction time varies depending on the above-mentioned concentration and temperature, but can usually be 0.5 to 20 hours. The amount of the raw material compound used is 0.5 to 3 times mol, preferably 0.9 to 1.5 times mol of the compound (2) with respect to the compound (3).

The solvent when X is a hydroxyl group is not particularly limited as long as it does not directly participate in this reaction, and examples thereof include benzene, toluene, xylene, methylnaphthalene, petroleum ether, ligroin, hexane, chlorobenzene, and dibenzene. Chlorinated or unchlorinated aromatic, aliphatic or alicyclic hydrocarbons such as chlorobenzene, methylene chloride, chloroform, dichloroethane, trichloroethylene, cyclohexane; ethers such as diethyl ether, tetrahydrofuran, dioxane, etc. Kind;
Amides such as N, N-dimethylformamide, N, N-dimethylacetamide and the like; a mixture of the above solvents and the like can be mentioned.

The amount of the solvent used may be such that the concentration of the compound (2) is in the concentration range of 2 to 80% by weight, preferably the compound (2).
It is preferable to use it so that the concentration thereof is 5 to 70% by weight. The dehydrating agent is not particularly limited, but WSCI
[1-ethyl-3- (3′-dimethylaminopropyl)
Carbodiimides such as carbodiimide], DCC [1,3-dicyclohexylcarbodiimide], DIPC [diisopropylcarbodiimide] and the like; BOP [benzotriazol-1-yl-tris (dimethylamino)]
Phosphonium hexafluorophosphide salt]; DPPA
[Diphenylphosphoryl azide] and the like can be mentioned, but carbodiimides such as WSCI and DCC are preferable.

The amount of the dehydrating agent used is the same as that of the compound (2).
It can be used in 0.5 to 5 times the molar amount of
The molar ratio is preferably 1.0 to 1.5 times. The reaction temperature is not particularly limited, but is within a temperature range from the ice cooling temperature to the boiling point of the solvent used or less, and preferably 0 to 30 ° C. The reaction time varies depending on the above-mentioned concentration and temperature, but is usually 0.3 to 2 hours. The amount of the raw material compound used is 0.5 to 2 times mol of the compound (3) with respect to the compound (2), but preferably 1.0 to 1.5.
It is preferable that the molar ratio is double. Compound (2) can be easily produced by the following method known per se.

[0044]

[Chemical 9]

(In the formula, R¹, R²And R⁷Is the same as above
Righteous. ) Examples of the compound (2) include, for example, Tables 1 to 5
Is it the type of each substituent corresponding to compounds 1 to 34 shown in
Each compound (2) consisting of
(2) ₁~ Compound (2)₃₄Called. For example, the compound
(2)₁Is R¹Is a methyl group, and R²Is t-butyl
A group, X is a halogen atom, R⁷O group (however, R⁷
Represents an alkyl group having 1 to 6 carbon atoms. ) Or hydroxyl group
is there. ]. Compound (3) is a compound known per se as shown below.
It can be easily manufactured by the method.

[0046]

[Chemical 10]

(In the formula, R³, R^Four, R^FiveAnd A¹Is the above
Is synonymous with; Y represents a halogen atom. )Compound
Examples of (3) include compound 1 shown in Tables 1 to 5.
Each compound consisting of each substituent type corresponding to
(3) can be mentioned [compound (3) ₁~Compound
(3)₃₄Called. For example, compound (3)₁Is R³But
Methyl group, R ^FourIs a 2-methoxyethyl group, R^FiveIs hydrogen
Child, A¹Is an ethylene group. ].

Target compound produced as described above
(1) is a standard method for extracting, concentrating, filtering, etc. after completion of the reaction.
Post-treatment, recrystallization and various chromatographs if necessary
It can be appropriately purified by a known means such as fee.
Examples of the compound (1) include compounds shown in Tables 1 to 5
Compounds 1 to 34 can be mentioned [for example, compound 1
Is R¹Is a methyl group, R²Is a t-butyl group, R ³Is meth
Lu group, R^FourIs a 2-methoxyethyl group, R^FiveIs a hydrogen atom,
A¹Is an ethylene group. ].

The pests which can be controlled by the compound (1) of the present invention include agricultural and horticultural pests [eg, Hemiptera (Plants, leafhoppers, aphids, whiteflies, etc.), Lepidoptera (Beetle beetles). , Plutella xylostella, Pseudococcidae, Beetle moth, Singing beetle, Pieris rapae, Coleoptera (Galloridae, Weevil, Chrysomelidae, Scarabaeidae, etc.) )], Sanitary pests (for example, flies, mosquitoes, cockroaches, etc.), stored-grain pests (Beetle beetles, bean weevils, etc.), root-knot nematodes, pine wood nematodes, and ticks, and agro-horticultural pathogens ( For example, wheat leaf rust, barley powdery mildew, cucumber downy mildew, rice blast, toma Epidemics, etc.) can be mentioned.

The pest control agent of the present invention is used for remarkable insecticidal
It has acaricidal and bactericidal effects and contains one or more compounds (1) as active ingredients. Compound (1)
Can be used alone, but is usually mixed with a carrier, a surfactant, a dispersant, an auxiliary agent, etc. by a conventional method (for example, powders, emulsions, fine granules, granules, wettable powders, oily preparations). (Prepared as a composition such as a suspension or an aerosol) is preferably used.

As the carrier, for example, solid carriers such as talc, bentonite, clay, kaolin, diatomaceous earth, white carbon, vermiculite, slaked lime, silica sand, ammonium sulfate, urea; hydrocarbons (kerosene, mineral oil, etc.), aromatic carbonization Hydrogen (benzene, toluene, xylene, etc.), chlorinated hydrocarbons (chloroform, carbon tetrachloride, etc.), ethers (dioxane, tetrahydrofuran, etc.), ketones (acetone, cyclohexanone, isophorone, etc.), esters (ethyl acetate, ethylene) Liquid carriers such as glycol acetate, dibutyl maleate, etc.), alcohols (methanol, n-hexanol, ethylene glycol, etc.), polar solvents (dimethylformamide, dimethylsulfoxide, etc.), water; air, nitrogen, carbon dioxide, freon, etc. Body carrier (in this case, can be mixed injection), and the like.

Examples of surfactants and dispersants that can be used to improve the performance of the present agent such as adhesion to animals and plants, absorption, drug dispersion, emulsification, spreading and the like include alcohol sulfates, alkyl sulfates and alkyls. Examples thereof include sulfonate, lignin sulfonate, polyoxyethylene glycol ether and the like. In order to improve the properties of the preparation, for example, carboxymethyl cellulose, polyethylene glycol, gum arabic or the like can be used as an auxiliary agent.

In the preparation of the present agent, the above-mentioned carrier, surfactant, dispersant and auxiliary agent can be used alone or in suitable combination according to the purpose.
The concentration of the active ingredient when the compound (1) of the present invention is formulated is usually 1 to 50% by weight in the case of emulsion and 0.3 in the case of powder.
25% by weight, usually 1 to 90% by weight for wettable powders, usually 0.5 to 5% by weight for granules, usually 0.5 to 5% by weight for oils, usually 0.1 to 5% by weight for aerosols. is there. These formulations can be diluted to an appropriate concentration and sprayed on the surface of plant foliage, soil, water surface of paddy fields or directly applied to various applications depending on the purpose.

[0054]

EXAMPLES The present invention will be specifically described below with reference to examples. It should be noted that these examples do not limit the scope of the present invention. Example 1 [Synthesis of Compound (1)] (1) N- {2- [4- (2-methoxyethyl) -2-methylphenoxy] ethyl} -3-t-butyl-1-methyl-5-pyrazole Synthesis of carboxamide (Compound 1) 2- [4- (2-Methoxyethyl) -2-methylphenoxy] ethylamine (2.1 g) and triethylamine (1.1 g) were dissolved in toluene (30 ml) and stirred under cooling. And a solution of 3-t-butyl-1-methyl-5-pyrazolecarboxylic acid chloride (2.0 g) in toluene (10
(ml) was added dropwise, and the mixture was stirred at room temperature for 1 hr. After completion of the reaction, water (10 ml) was added, the toluene layer was separated, the toluene layer was washed with water, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained oily substance was isolated by column chromatography (Wakogel C-200, eluted with toluene: ethyl acetate = 4: 1) and then recrystallized from n-hexane to obtain 3.0 g of the objective substance as colorless needle crystals. It was

¹ H-NMR (CDCl ₃ , δppm) 1.29 (s, 9H), 2.24 (s, 3H), 2.8
0 (t, 2H), 3.35 (s, 3H), 3.56
(T, 2H), 3.80 (q, 2H), 4.09 (q,
2H), 4.11 (s, 3H), 6.30 (s, 1
H), 6.42 (b, 1H), 6.74 (d, 1H),
7.00 (d, 1H), 7.02 (s, 1H)

(2) Synthesis of N- {2- [4- (2-ethoxyethyl) -2-methylphenoxy] ethyl} -3-t-butyl-1-methyl-5-pyrazolecarboxamide (Compound 2) 2 -[4- (2-Ethoxyethyl) -2-methylphenoxy] ethylamine (6.7g) and 3-t-butyl-1-
Methyl-5-pyrazolecarboxylic acid methyl ester (7.0 g) was dissolved in toluene (40 ml) and then 28% sodium methoxide in methanol (0.
6 g) was added and the mixture was heated under reflux for 5 hours. After completion of the reaction, the mixture was cooled to room temperature, washed with water, the organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. By recrystallizing the obtained concentrate with n-hexane, 1
0.6 g was obtained.

¹ H-NMR (CDCl ₃ , δppm) 1.21 (t, 3H), 1.30 (s, 9H), 2.2
6 (s, 3H), 2.82 (t, 2H), 3.54
(Q, 2H), 3.60 (t, 2H), 3.83 (q,
2H), 4.10 (t, 2H), 4.12 (s, 3)
H), 6.30 (s, 1H), 6.42 (b, 1H),
6.75 (d, 1H), 7.00 (d, 1H), 7.0
2 (s, 1H)

(3) N- {2- [4- (2-ethoxyethyl) -2,3-dimethylphenoxy] ethyl} -3-t-
Synthesis of Butyl-1-methyl-5-pyrazolecarboxamide (Compound 3) 2- [4- (2-Ethoxyethyl) -2,3-dimethylphenoxy] ethylamine (7.2 g) and 3-t-butyl-1- Methyl-5-pyrazolecarboxylic acid methyl ester (8.8 g) was dissolved in toluene (40 ml), 28% sodium methoxide methanol solution (1.7 g) was added, and the mixture was heated under reflux for 1 hr. After completion of the reaction, the mixture was cooled to room temperature, washed with water, the organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. By recrystallizing the obtained concentrate with n-hexane, 11.2 g of the desired product was obtained.

¹ H-NMR (CDCl ₃ , δppm) 1.21 (t, 3H), 1.29 (s, 9H), 2.2
0 (s, 3H), 2.24 (s, 3H), 2.89
(T, 2H), 3.46 to 3.58 (m, 4H), 3.
81 (q, 2H), 4.10 (t, 2H), 4.12
(S, 3H), 6.30 (s, 1H), 6.40 (b,
1H), 6.68 (d, 1H), 7.00 (d, 1H)

(4) N- {2- [4- (2-ethoxyethyl) -2,6-dimethylphenoxy] ethyl} -3-t-
Synthesis of butyl-1-methyl-5-pyrazolecarboxamide (Compound 4) 2- [4- (2-ethoxyethyl) -2,6-dimethylphenoxy] ethylamine (7.2 g) and 3-t-butyl-1- Methyl-5-pyrazolecarboxylic acid methyl ester (7.1 g) was dissolved in toluene (30 ml), then powdered sodium methoxide (1.1 g) was added,
The mixture was heated under reflux for 5 hours. After completion of the reaction, the mixture was cooled to room temperature, washed with water, the organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. By recrystallizing the obtained concentrate with n-hexane, 10.5 g of the desired product was obtained.

(5) N- {2- [4- (2-ethoxyethyl) -2,3-dimethylphenoxy] ethyl} -3-t-
Synthesis of Butyl-5-pyrazolecarboxamide (Compound 5) 2- [4- (2-Ethoxyethyl) -2,3-dimethylphenoxy] ethylamine (4.3 g) and ethyl 3-t-butyl-5-pyrazolecarboxylate Esters (3.6
g) and dissolved in toluene (50 ml), then 28%
A methanol solution of sodium methoxide (5.2 g) was added, and the mixture was heated under reflux for 20 hours. After completion of the reaction, the mixture was cooled to room temperature, water was added, and the mixture was extracted with ethyl acetate. The extract was washed with water, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained oily substance was subjected to column chromatography (Wakogel C-200, toluene: ethyl acetate = 4:
Isolation (1 elution) and washing with n-hexane gave 5.4 g of the desired product as colorless powdery crystals.

¹ H-NMR (CDCl ₃ , δppm) 1.20 (t, 3H), 1.31 (s, 9H), 2.1
8 (s, 3H), 2.22 (s, 3H), 2.88
(T, 2H), 3.47 to 3.56 (m, 4H), 3.
83 (q, 2H), 4.09 (t, 2H), 6.61
(S, 1H), 6.68 (d, 1H), 6.95 (d,
1H), 7.38 (b, 1H), 10.35 (b, 1
H)

(6) N- {2- [4- (2-ethoxyethyl) -2,3-dimethylphenoxy] ethyl} -3-t-
Synthesis of butyl-1-ethyl-5-pyrazolecarboxamide (Compound 6) 2- [4- (2-ethoxyethyl) -2,3-dimethylphenoxy] ethylamine (0.7 g) and triethylamine (0.8 g) Dissolve in toluene (10 ml),
A toluene solution (10 ml) of 3-t-butyl-1-ethyl-5-pyrazolecarboxylic acid chloride (0.6 g) was added dropwise with cooling and stirring, and then the mixture was stirred at room temperature for 1 hour. After completion of the reaction, water (10 ml) was added, the toluene layer was separated, the toluene layer was washed with water, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained oily substance was isolated by column chromatography (Wakogel C-200, toluene: ethyl acetate = 4: 1 elution), and then n
-Recrystallize with hexane to give the desired product as colorless needle crystals.
g was obtained.

¹ H-NMR (CDCl ₃ , δppm) 1.20 (t, 3H), 1.29 (s, 9H), 1.4
0 (t, 3H), 2.20 (s, 3H), 2.24
(S, 3H), 2.89 (t, 2H), 3.46-3.
57 (m, 4H), 3.81 (q, 2H), 4.10
(T, 2H), 4.53 (q, 2H), 6.28 (s,
1H), 6.38 (b, 1H), 6.67 (d, 1
H), 7.00 (d, 1H)

(7) N- {2- [4- (2-ethoxyethyl) -2-methylphenoxy] ethyl} -1-methyl-
Synthesis of 3-n-propyl-5-pyrazolecarboxamide (Compound 9) 2- [4- (2-ethoxyethyl) -2-methylphenoxy] ethylamine (3.3 g) and 1-methyl-3-n-
Propyl-5-pyrazolecarboxylic acid ethyl ester (2.9 g) was dissolved in toluene (30 ml), and then 28% sodium methoxide in methanol (2.
9 g) was added, and the mixture was heated under reflux for 8 hours. After completion of the reaction, the mixture was cooled to room temperature, water was added, and the mixture was extracted with ethyl acetate. The extract was washed with water, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained oily substance was isolated by column chromatography (Wakogel C-200, toluene: ethyl acetate = 9: 1 elution) and then recrystallized from n-hexane to obtain 2.5 g of the objective substance as colorless needle crystals. It was

¹ H-NMR (CDCl ₃ , δppm) 0.95 (t, 3H), 1.20 (t, 3H), 1.6
5 (q, 2H), 2.23 (s, 3H), 2.57
(T, 2H), 2.80 (t, 2H), 3.50 (q,
2H), 3.59 (t, 2H), 3.81 (q, 2)
H), 4.10 (s, 3H), 4.11 (t, 2H),
6.25 (s, 1H), 6.41 (s, 1H), 6.7
4 (d, 1H), 7.00 (d, 1H), 7.01
(S, 1H)

(8) N- {2- [4- (2-ethoxyethyl) -2-methylphenoxy] ethyl} -1-methyl-
Synthesis of 3-i-propyl-5-pyrazolecarboxamide (Compound 10) 2- [4- (2-Ethoxyethyl) -2-methylphenoxy] ethylamine (2.1 g) and triethylamine (1.1 g) were added to toluene ( 30 ml), and a solution of 1-methyl-3-i-propyl-5-pyrazolecarboxylic acid chloride (1.6 g) in toluene (5 g) with cooling and stirring.
(ml) was added dropwise, and the mixture was stirred at room temperature for 1 hr. After the reaction was completed, water (10 ml) was added, the mixture was extracted with ethyl acetate, the extract was washed with water, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained oily substance was isolated by column chromatography (Wakogel C-200, eluted with toluene: ethyl acetate = 5: 1) and then recrystallized from n-hexane to obtain 2.2 g of the desired product as colorless needle crystals. It was

¹ H-NMR (CDCl ₃ , δppm) 1.20 (t, 3H), 1.25 (d, 6H), 2.2
3 (s, 3H), 2.81 (t, 2H), 2.96
(Q, 1H), 3.51 (q, 2H), 3.60 (t,
2H), 3.81 (t, 2H), 4.10 (s, 3
H), 4.12 (t, 2H), 6.28 (s, 1H),
6.40 (b, 1H), 6.76 (d, 1H), 7.0
1 (d, 1H), 7.02 (s, 1H)

(9) N- {2- [4- (2-ethoxyethyl) -2-methylphenoxy] ethyl} -1-methyl-
Synthesis of 3-Cyclopropyl-5-pyrazolecarboxamide (Compound 11) 2- [4- (2-Ethoxyethyl) -2-methylphenoxy] ethylamine (4.1 g) and 1-methyl-3-cyclopropyl-5- Pyrazolecarboxylic acid ethyl ester (3.5 g) was dissolved in toluene (20 ml).
Then, a 28% sodium methoxide methanol solution (3.5 g) was added, and the mixture was heated under reflux for 8 hours. After completion of the reaction, the mixture was cooled to room temperature, water was added, the mixture was extracted with ethyl acetate, the extract was washed with water and dried over anhydrous sodium sulfate,
The solvent was distilled off under reduced pressure. The obtained oil was isolated by column chromatography (Wakogel C-200, eluted with toluene: ethyl acetate = 4: 1) to obtain 3.0 g of the target product as a colorless oil.

¹ H-NMR (CDCl ₃ , δppm) 0.66 to 0.73 (m, 2H), 0.88 to 0.95
(M, 2H), 1.21 (t, 3H), 1.84 to 1.
95 (m, 1H), 2.23 (s, 3H), 2.81
(T, 2H), 3.50 (q, 2H), 3.58 (t,
2H), 3.80 (q, 2H), 4.08 (s, 3
H), 4.10 (t, 2H), 6.12 (s, 1H),
6.37 (s, 1H), 6.75 (d, 1H), 7.0
1 (d, 1H), 7.02 (s, 1H)

(10) N- {2- [4- (2-ethoxyethyl) -2-methylphenoxy] ethyl} -1-methyl-
Synthesis of 3-trifluoromethyl-5-pyrazolecarboxamide (Compound 12) 2- [4- (2-Ethoxyethyl) -2-methylphenoxy] ethylamine (3.1 g) and 1-methyl-3-trifluoromethyl- 5-pyrazolecarboxylic acid (2.5
g) and were dissolved in methylene chloride (20 ml) and ice-cooled. Then 1-ethyl-3- (3′-dimethylaminopropyl) carbodiimide hydrochloride (2.8 g) was added,
It was stirred at room temperature for 1 hour. After the reaction was completed, water was added and the mixture was extracted with methylene chloride. The extract was washed with water, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained oily substance was subjected to column chromatography (Wako Gel C-2
00, toluene: ethyl acetate = 6: 1 elution),
Then, it was washed with n-hexane to obtain 2.3 g of the target substance as colorless powdery crystals.

¹ H-NMR (CDCl ₃ , δppm) 1.20 (t, 3H), 2.22 (s, 3H), 2.8
1 (t, 2H), 3.40 (q, 2H), 3.59
(T, 2H), 3.85 (q, 2H), 4.13 (t,
2H), 4.22 (s, 3H), 6.45 (b, 1)
H), 6.71 (s, 1H), 6.75 (d, 1H),
7.00 (d, 1H), 7.02 (s, 1H)

(11) Synthesis of N- [2- (4-t-butylphenoxy) ethyl] -3-t-butyl-1-methyl-5-pyrazolecarboxamide (Compound 29) 2- (4-t-butyl) Phenoxy) ethylamine (2.9
g) and 3-t-butyl-1-methyl-5-pyrazolecarboxylic acid ethyl ester (3.2 g) were added to toluene (30 g).
ml). Then, a 28% sodium methoxide methanol solution (3.2 g) was added, and the mixture was heated under reflux for 4 hours. After completion of the reaction, the mixture was cooled to room temperature, water was added, the mixture was extracted with ethyl acetate, the extract was washed with water, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained oily substance was subjected to column chromatography (Wako Gel C-2
00, toluene: ethyl acetate = 4: 1 elution) to obtain 3.9 g of the desired product as colorless powdery crystals.

¹ H-NMR (CDCl ₃ , δppm) 1.30 (s, 18H), 3.81 (q, 2H), 4.
12 (q, 2H), 4.14 (s, 3H), 6.35
(S, 1H), 6.50 (b, 1H), 6.85 (m,
1H), 7.31 (m, 1H)

(12) Synthesis of other compounds (1) in Tables 1 to 5 Other compounds (1) in Tables 1 to 5 were synthesized according to the methods described in (1) to (11) above. did. The compounds synthesized as described above are shown in Tables 1 to 5.

[0076]

[Table 1]

[0077]

[Table 2]

[0078]

[Table 3]

[0079]

[Table 4]

[0080]

[Table 5]

Example 2 [Preparation of preparation] (1) Preparation of granules 5 parts by weight of compound 1, 35 parts by weight of bentonite, 57 parts by weight of talc, 1 part by weight of neoperex powder (trade name; manufactured by Kao Corporation) And 2 parts by weight of sodium lignin sulfonate were uniformly mixed, and then a small amount of water was added and kneaded, and then granulated and dried to obtain granules.

(2) Preparation of Wettable Powder 10 parts by weight of compound 1, 70 parts by weight of kaolin, 18 parts by weight of white carbon, 1.5 parts by weight of neoperex powder (trade name; manufactured by Kao Corporation) and demol (product) Name; made by Kao Co., Ltd.) and 0.5 parts by weight, and
Then, it was pulverized to obtain a wettable powder.

(3) Preparation of Emulsion To 20 parts by weight of compound 1 and 70 parts by weight of xylene, 10 parts by weight of toxanone (trade name; manufactured by Sanyo Kasei Co., Ltd.) were added and mixed uniformly to obtain an emulsion. .

(4) Preparation of Dust Formulation 5 parts by weight of compound 1, 50 parts by weight of talc and 4 of kaolin
A powder was obtained by uniformly mixing 5 parts by weight.

Example 3 [Efficacy test] (1) Efficacy test against diamondback moth A compound (1) shown in Tables 1 to 5 prepared according to Example 2
30% of each wettable powder in water containing surfactant (0.01%)
After diluting to 0 ppm, cabbage leaf pieces (5 × 5 cm) were dipped in each of these chemical solutions for 30 seconds, placed in each plastic cup one by one and air dried. Next, in each of these cups, 10 diamondback moths (third instar larvae) were released, and the cups were capped.
The cup was allowed to stand in a constant temperature room at 5 ° C., and two days later, the number of live and dead insects in each cup was counted to determine the mortality rate. The insecticidal effect is evaluated in four stages (A: 100%, B: less than 100% depending on the range of mortality).
80%, C: less than 80 to 60%, D: less than 60%). The results are shown in Table 6.

[0086]

[Table 6]

(2) Efficacy test against adult female worms of the genus Acarina compound shown in Tables 1 to 5 prepared according to Example 2 (1)
30% of each wettable powder in water containing surfactant (0.01%)
Each kidney bean leaf piece (diameter: 20 m) diluted to 0 ppm and infested with 10 adult female adults
m) was immersed for 15 seconds each. Next, each leaf piece was left in a constant temperature room at 25 ° C., and three days later, the number of live and dead mites in each leaf piece was counted to determine the miticidal rate. The evaluation of the acaricidal effect is carried out in four stages (A: 100%, depending on the range of the acaricidal rate).
B: less than 100 to 80%, C: less than 80 to 60%, D:
(Less than 60%). The results are shown in Table 7.

[0088]

[Table 7]

(3) Efficacy test against Nicaria spp. Eggs Compounds (1) shown in Tables 1 to 5 prepared according to Example 2
30% of each wettable powder in water containing surfactant (0.01%)
Each bean leaf piece (20 mm in diameter) was diluted to 0 ppm, and 5 adult female adult mites of each species were produced and laid in each of these drug solutions, and then the adult was removed for 10 seconds. Next, these leaf pieces were left in a constant temperature room at 25 ° C., and after 6 days, the number of unhatched eggs in each leaf piece was counted to determine the ovicidal rate.
The evaluation of the ovicidal effect was shown in four levels (A: 100%, B: less than 100 to 80%, C: less than 80 to 60%, D: less than 60%) depending on the range of the ovicidal rate. The results are shown in Table 8.

[0090]

[Table 8]

(4) Control efficacy test against barley powdery mildew (preventive effect) Ten barley (cultivar: black wheat) was grown in a plastic flower pot with a diameter of 6 cm, and seedlings of 1.5 leaf stage were grown. In addition, each wettable powder of the compound (1) shown in Tables 1 to 5 prepared according to Example 2 was mixed with a surfactant (0.01%).
Each of them was sprayed with 20 ml per one pot by diluting each to 500 ppm with water containing water. These were cultivated in a glass greenhouse for 2 days, and then the barley powdery mildew fungus conidia spores were collected from the diseased leaves and sprinkled evenly over the plants to inoculate. Next, these were grown in a glass greenhouse for one week, and the degree of barley powdery mildew lesions appearing on each first leaf was investigated. The evaluation of the bactericidal effect was carried out in 6 stages (0: the entire diseased,
1: Lesion area is about 60%, 2: Lesion area is about 40%, 3: Lesion area is about 20%, 4: Lesion area is 10%
Hereinafter, 5: no lesions). The results are shown in Table 9.

[0092]

[Table 9]

(5) Control efficacy test against cucumber downy mildew One cucumber (cultivar: Sagamihanjiro) was grown in a plastic flower pot with a diameter of 6 cm, and seedlings were planted on a 1.5 leaf stage seedling. A wettable powder prepared from the compound (1) shown in 1 to 5 according to Example 2 was diluted to 500 ppm with water containing a surfactant (0.01%), and 20 ml per pot.
I sprayed them one by one. After spraying, cultivate in a glass greenhouse for 2 days, then cucumber downy mildew (Pseudoperonospora cubensi
The zoosporangium of s) was prepared from the diseased leaf, and this was uniformly spray-inoculated on the back surface of the plant leaf. 2 days after inoculation, 20 ℃
After keeping it in the dark in a glass greenhouse, it was grown in a glass greenhouse for 5 days, and the degree of cucumber downy mildew lesions appearing on the first leaf was investigated.

The results of the evaluation of the bactericidal effect are shown in Table 10 by the 6-step evaluation method described in (4) above.

[0095]

[Table 10]

[0096]

The pest control agent for agricultural and horticultural use containing the novel phenoxyalkylamine derivative of the present invention as an active ingredient has excellent effects such as insecticidal, acaricidal and bactericidal.

 ─────────────────────────────────────────────────── ─── Continuation of front page (72) Inventor Akira Ooka 5 1978, Ogushi, Ube City, Yamaguchi Prefecture 5 1978, Ube Research Co., Ltd. (72) Inventor Kiyoshi Omori 5 5 1978, Ogushi, Ube, Yamaguchi Prefecture Ube Industries Ube Institute Co., Ltd.

Claims (3)

[Claims] 1. The following formula (1): [In the formula, R ¹ represents an alkyl group having 1 to 4 carbon atoms or a hydrogen atom; R ² is an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, or 1 to 4 carbon atoms; R 4 represents an haloalkyl group; R ³ represents an alkyl group having 1 to 4 carbon atoms, a hydrogen atom or a halogen atom; R ⁴ represents A ² —O
—R ⁶ (wherein A ² represents an alkylene group having 1 to 4 carbon atoms, R ⁶ represents an alkyl group having 1 to 4 carbon atoms, 3 to 3 carbon atoms)
It represents 5 alkenyl groups or alkynyl groups having 3 to 5 carbon atoms. ), A hydrogen atom, an alkyl group having 1 to 12 carbon atoms, a halogen atom or an alkenyl group having 3 to 5 carbon atoms; R ⁵ represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms or a halogen atom. A ¹ represents an alkylene group having 1 to 5 carbon atoms. Provided that R ¹ represents an alkyl group having 1 to 4 carbon atoms or a hydrogen atom; R ² represents an alkyl group having 1 to 6 carbon atoms; R ³ represents an alkyl group having 1 to 5 carbon atoms;
Represents a hydrogen atom or a halogen atom; R ⁴ is A ² —O—R
⁶ (Note that A ² represents an alkylene group having 1 to 4 carbon atoms, R ⁶ represents an alkyl group having 1 to 4 carbon atoms, and 3 to 5 carbon atoms.
Represents an alkenyl group or an alkynyl group having 3 to 5 carbon atoms. ), Represents a hydrogen atom, an alkyl group or the number 3-5 alkenyl group having a carbon of 1 to 5 carbon atoms; R ⁵ represents a hydrogen atom, an alkyl group or a halogen atom having 1 to 4 carbon atoms; A ¹ Excludes the case of representing an alkylene group having 2 to 5 carbon atoms. ] The phenoxy alkylamine derivative shown by these. 2. The following formula (2): [Wherein R ¹ and R ² have the same meanings as described in claim 1;
X is a halogen atom, R ⁷ O group (where R ⁷ is a carbon number of 1 to
Represents 6 alkyl groups. ) Or a hydroxyl group. ] And a pyrazolecarboxylic acid derivative represented by the following formula (3): (Wherein R ³ , R ⁴ , R ⁵ and A ¹ have the same meanings as described in claim 1) and a phenoxyalkylamine represented by the formula (1) is reacted. A method for producing a phenoxyalkylamine derivative represented by 1). 3. A pesticide for agricultural and horticultural use, which comprises the phenoxyalkylamine derivative represented by the formula (1) according to claim 1 as an active ingredient.