JPH03153668A - Pyrazoleamides and insecticide or acaricide containing the same as active ingredient - Google Patents

Abstract

NEW MATERIAL:A pyrazoleamide of formula I [R<1> is alkyl; R<2> is N, alkyl or alkoxy; X is H, halogen, alkyl, alkoxy or haloalkoxy; or R<2> and X form a group of formula II or III (R<4> is H or alkyl); R<3> is H, halogen, alkyl, alkenyl, alkynyl, cycloalkyl, alkoxy, haloalkyl, phenyl, alkylthio, etc., or forms a group of formula IV (R<5> and R<6> are H or alkyl) together with the adjacent R<3>; m is 1-3; n is 1-4]. EXAMPLE:N-[2-(4-n-Pentylphenoxy)ethyl]-4-chloro-3-ethyl-1-methyl-5- pyrazolecarboxamide. USE:An insecticide or acaricide. PREPARATION:For example, a compound of formula V is reacted with a compound of formula VI to provide the compound of formula I.

Description

DETAILED DESCRIPTION OF THE INVENTION [Field of Industrial Application] The present invention relates to novel pyrazole amides and insecticides and acaricides containing the same as an active ingredient.

[Problems to be solved by conventional technology and invention]

In recent years, due to the long-term use of insecticides, insect pests have developed resistance, making it difficult to control them with conventional insecticides. It has become difficult to control. or,
Development of resistance to synthetic pyrethroid insecticides, which have attracted attention in recent years, has also been reported. On the other hand, some organic phosphorus agents or carbamate agents are highly toxic, and others disturb the ecosystem due to their persistence, creating an extremely worrying situation. Therefore, the development of new insecticides that exhibit excellent control effects even against insect pests that are resistant to conventional insecticides, and that have low toxicity and low persistence are expected.

[Means for solving problems]

The present inventors conducted extensive research to address this situation, and as a result, discovered novel pyrazoles having excellent insecticidal and acaricidal activity, and completed the present invention.

That is, the gist of the present invention resides in pyrazole amides represented by the following formula (I) and insecticides and acaricides containing the same as an active ingredient.

(In the above formula, R1 represents an alkyl group of CI-Ca, and R
t is a hydrogen atom, a C3-C4 alkyl group, or 01-C4
represents an alkoxy group, X is a hydrogen atom, a halogen atom,
The alkyl group of CI to C1, the alkoxy group of 01 to C4, or the haloalkoxy group of 01 to C5 is a hydrogen atom or
~C1 alkyl group. ), R3 is each independently a hydrogen atom, a halogen atom, a C1-C1 alkyl group s
C3-C3 alkenyl group, C1-C2 alkynyl group, C! -C5 cycloalkyl group, C8-C4 alkoxy group, 01-C4 haloalkoxy group, trifluoromethyl group, nitro group, cyano group, phenyl group, phenoxy group, cz-C1 alkylcarbonyl group, 02-C3
alkoxycarbonyl group, trimethylsilyl group, C1
~C4 alkylthio group or adjacent Rj together R5,
R6 each independently represents a hydrogen atom or a C1-C4 alkyl group. ). m represents 1.2 or 3, n represents 1,
2.3 or 4 is shown. ) Hereinafter, the present invention will be explained in detail. - In composition (I), R1 is a methyl group, an ethyl group,
CI~ such as n-propyl group, isopropyl group, n-butyl group, isobutyl group, 5ec-butyl group, t-butyl group, etc.
C4 represents a straight or branched alkyl group, preferably a methyl group or an ethyl group, R2 is a hydrogen atom; a methyl group,
CI to C1 straight or branched alkyl groups such as ethyl group, n-propyl group, isopropyl group, n-butyl group,
Alternatively, it represents a CI'' C4 straight or branched alkoxy group such as a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, an n-butoxy group, a 3ec-butoxy group, a t-butoxy group, and preferably , represents a methyl group, an ethyl group, or a methoxy group; 01-C4 linear or branched alkyl groups such as 5ec-butyl group, -butyl group; methoxy group, ethoxy group, n-propoxy group, isopropoxy group, n-butoxy group, isobutoxy group, 5ec- 01-C1 linear or branched alkoxy groups such as butoxy group, t-butoxy group; monofluoromethoxy group, monochloromethoxy group, monobromomethoxy group, difluoromethoxy group, dichloromethoxy group, dibromomethoxy group, trifluoromethoxy group group, trichloromethoxy group, tribromomethoxy group, chlorofluoromethoxy group, bromofluoromethoxy group, bromochloromethoxy group, 2,2.
2-trifluoroethoxy group, 2.2.2-)lichloroethoxy group, 2,2.2-tribromoethoxy group, 2-
Chloro-2,2-difluoroethoxy group, 2-bromo-
2,2-difluoroethoxy group, 2,2,3.3.3-
Pentafluoro-n-propoxy group, 2,2.3.3-
It represents a C8-C1 straight or branched haloalkoxy group such as a tetrafluoro-n-propoxy group or a 2,2゜2-trifluoro-isopropoxy group, preferably a hydrogen atom; a fluorine atom, a chlorine atom, a bromine atom. Halogen atoms such as atoms; C5 to C4 straight or branched chains such as methyl group, ethyl group, n-propyl group, isopropyl group, n-7' thyl group, isobutyl group, 5ec-butyl group, t-butyl group, etc. Alkyl group; CI- such as methoxy group, ethoxy group, n-propoxy group, isopropoxy group, n-butoxy group, isobutoxy group, 5ec-butoxy group, t-butoxy group, etc.
C, represents a straight or branched alkoxy group, more preferably a hydrogen atom, a chlorine atom, a methyl group or an n-butoxy group. In addition, R2 and X together represent a hydrogen atom or a 01-C1 linear or branched alkyl group such as a methyl group, ethyl group, n-propyl group, isopropyl group, preferably a hydrogen atom. . ), R3 is each independently a hydrogen atom, 2 halogen atoms such as a fluorine atom, a chlorine atom, a bromine atom, etc.: methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec -butyl group, t-butyl group, n-amyl group, isoamyl 5, t-pentyl group, n-he-Jr', y
4, ethyl-1-methylpropyl group, n-heptyl group, etc. straight chain or branched alkyl group of Cl-07; 1
-03 to C1 of propenyl group, allyl group, methallyl group, 1-butenyl group, 2-butenyl group, 2-pentenyl group, etc.
alkenyl group: 1-propynyl group, propargyl group,
C3 to C3 alkynyl groups such as 2-butynyl group and 2-pentynyl group; C1 to C4 cycloalkyl groups such as cyclopropyl group, cyclobutyl group, cyclopentyl group, and cyclohexyl group; methoxy group, ethoxy group, n-propoxy group , isopropoxy group, n-butoxy group, isobutoxy group, 5ec-butoxy group, t-butoxy group, etc.
C4 straight or branched alkoxy group; monofluoromethoxy group, difluoromethoxy group, trifluoromethoxy group, 2-fluoroethoxy group, 2-chloroethoxy group, 2,2.2-trifluoroethoxy group, 2.2 .2
-) Lichloroethoxy group, 3-chloropropoxy group, 3
-bromopropoxy group, 3,3.3-)lifluoropropoxy group, 2.2,3.3-tetrafluoropropoxy group, 2.2,3,3.3-pentafluoropropoxy group, 2.2-dichloro -3,3,3-trifluoropropoxy group, 1-trifluoromethylethoxy group, 1.3-
Difluoro-2-propoxy group, 1.1,1,3,3.
3-hexafluoro-2-propoxy group, 3,3.3-
) Lichlorobroboxy group, 4-chlorobutoxy group, 4,
4.4-trifluorobutoxy group, 3.3,4,4.4
-pentafluorobutoxy group, 2.2.3, 3, 4.4
-hexafluorobutoxy group, 2.2.3,4°4.4
-hekifluorobutoxy group, 2,2.3°3.4,4.
01-C4 straight or branched haloalkoxy group such as 4-hebutafluorobutoxy group, ■-trifluoromethylpropoxy group, 1.1,1゜2.2-pentafluoro-3-butoxy group; trifluoro Methyl group; Nitro group;
Cyano group; phenyl group; phenoxy group; methylcarbonyl group, ethylcarbonyl group, n-propylcarbonyl group, isopropylcarbonyl group, n-butylcarbonyl group, isobutylcarbonyl group, 5ec-butylcarbonyl group, t-butylcarbonyl group, etc. 02~CS straight or branched alkylcarbonyl group; methoxycarbonyl group, ethoxycarbonyl group, n-propoxycarbonyl group, isopropoxycarbonyl group, n-butoxycarbonyl group, isobutoxycarbonyl group, 5ee-butoxycarbonyl group, t -02-C such as butoxycarbonyl group
7 straight or branched alkoxycarbonyl group; trimethylsilyl group or methylthio group, ethylthio group, n-
Propylthio group, isopropylthio group, n-butylthio group, inbutylthio group, 5ec-butylthio group, t-
Indicates a CI-C4 straight chain or branched alkylthio group such as a butylthio group, preferably a hydrogen atom; a halogen atom such as a fluorine atom, a chlorine atom, a bromine atom; a methyl group, an ethyl group, an n-propyl group, an isopropyl group , n-butyl group, isobutyl group, 5ec-butyl group, t-butyl group,
C3 to C1 straight or branched alkyl groups such as n-amyl group, isoamyl group, t-pentyl group, n-hexyl group, 1-ethyl-1-methylpropyl group, n-hebutyl group; cyclopropyl group , C1-C8 cycloalkyl groups such as cyclobutyl group, cyclopentyl group, cyclohexyl group; methoxy group, ethoxy group, n-propoxy group, isopropoxy group, n-butoxy group, isobutoxy group, 5
01-C4 straight or branched alkoxy groups such as ec-butoxy group and t-butoxy group; Nitro group; Cyano group;
Phenyl group; Phenoxy group; Ct'' Cs straight chain or branched alkyl group such as methylcarbonyl group, ethylcarbonyl group, n-propylcarbonyl group, isopropylcarbonyl group; methoxycarbonyl group, ethoxycarbonyl group, n-propoxycarbonyl group , isopropoxycarbonyl group, n-butoxycarbonyl group, isobutoxycarbonyl group, 5ec-butoxycarbonyl group, t
-02 to C2 linear or branched alkoxycarbonyl group such as butoxycarbonyl group, or methylthio group, ethylthio group, n-propylthio group, isopropylthio group,
It represents a C8 to C4 straight or branched alkylthio group such as n-butylthio group, isobutylthio group, 5ec-butylthio group, t-butylthio group, and more preferably,
Hydrogen atom, chlorine atom, methyl group, n-propyl group, isopropyl group, 5ec-7" t-butyl group, n-
Amyl group, n-hexyl group, cyclohexyl group, methoxy group, n-butoxy group, nitro group, cyano group, phenyl group, phenoxy group, methylcarbonyl group, methoxycarbonyl L n-propoxycarbonyl group, methylthio group or n-butylthio group Indicates the group. In addition, adjacent R3 and R6 each independently represent a hydrogen atom or a methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, 5ec-butyl group, -butyl group, etc. It represents a C1-C4 straight or branched alkyl group, preferably a hydrogen atom. ). m represents 1.2 or 3, and n represents 1, 2.3 or 4.

Next, the method for producing the compound of the present invention will be described.

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

(If) (I) (In the above formula, R1, R1, X, R'', m and n are -
In the above-mentioned (n), aromatic hydrocarbons such as benzene, toluene or xylene; acetone, methyl ethyl ketone or methyl isobutyl; Ketones such as ketones; halogenated hydrocarbons such as chloroform or methylene chloride; water;
Esters, such as methyl acetate or ethyl acetate; The compound (1) represented by the above-mentioned formula -i can be obtained by reacting the compound (I[[) represented by the above-mentioned formula -i] in the presence of the compound (I[[)]. Examples of the base include sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, pyridine, and triethylamine.

Incidentally, the compound represented by the above-mentioned compound (II) is, for example, A
nnalen der Chemie.

Justus Liebig's, 536+
97 (1938). In addition, the compound represented by the above-mentioned -fir is, for example, phenoxyethyl bromide synthesized according to the method described in Qrg, 5ynth, Co1)゜Vol, Sat, 2nd Ed, 435 (1967). It can be easily produced by imidizing (chloride) with potassium phthalimide in a conventional manner and then decomposing it with hydrazine hydroxide in a conventional manner.

The compound represented by the above general formula (I) can also be produced according to the following reaction formula.

(In the above formula, R1, Rt, X, R', m and n are as defined in the above general formula (I).)
) and the compound represented by the above formula (V) and triphenylphosphine with diethyl ether,
Ethers such as 1,2-dimethoxyethane, tetrahydrofuran or dioxane; aromatic hydrocarbons such as benzene, toluene or xylene; halogenated hydrocarbons such as chloroform or methylene chloride By reacting a dicarboxylic acid ester, a compound represented by the above formula can be obtained.As the azodicarboxylic acid ester, diethyl ester or diisopropyl ester is preferable.

In addition, the compound represented by the above-mentioned compound (IV) is, for example,
-a It can be easily obtained by reacting a compound represented by formula (II) with a corresponding hydroxyalkylamine.

[For production]

-i The compound represented by formula (1) has remarkable control activity against the following insects of the orders Coleoptera, Lepidoptera, Hemiptera, Orthoptera, and Diptera, as well as rabbits and larvae of the order Acari that parasitize plants. However, it is of course not limited to these.

1 Hemiptera: Planthoppers such as the brown planthopper, brown planthopper, and brown planthopper, leafhoppers such as the black leafhopper and giant leafhopper, and aphids such as the green peach aphid 2 Lepidoptera: mealybugs, fall armyworms, fall armyworms, black borer moths, etc. 3 Coleoptera: bean weevils, etc. 4 Diptera: House fly, Culex mosquito, Culex mosquito, etc. 5 Spider mites: Two-spotted spider mite, two-spotted spider mite, orange spider mite, etc. When the compound of the present invention represented by general formula (1) is used as an insecticide or acaricide, it may be used alone. However, usually using adjuvants like conventional pesticides, emulsions,
It is formulated into powders, wettable powders, liquids, etc., and used as is or diluted. As adjuvants, those commonly used in insecticide formulations can be used. Solid carriers such as talc, kaolin, diatomaceous earth, clay, starch;
Water; solvents such as hydrocarbons such as cyclohexane, benzene, xylene, toluene, halogenated hydrocarbons such as chlorobenzene, ethers, amides such as dimethylformamide, ketones, alcohols, nitriles such as acetonitrile; Other known surfactants include emulsifiers and dispersants.

In addition, other insecticides, acaricides, fungicides,
It can also be mixed or used in combination with insect growth regulating substances, plant growth regulating substances, and the like.

The concentration of active ingredients in formulated insecticides and acaricides is not particularly limited, but powders usually range from 0.5 to 20
The weight percent is preferably 1 to 10 weight percent, the hydrating agent is 1 to 90 weight percent, preferably 10 to 80 weight percent, and the emulsion is 1 to 90 weight percent, preferably 10 to 40 weight percent.

When the compound represented by formula (I) above is used as an insecticide, the active ingredient is usually used at a concentration of 5 to 1000 ppm, preferably 10 to 500 ppm.

〔Example〕

Next, the present invention will be explained in more detail with reference to production examples, formulation examples, and test examples of the compounds of the present invention, but the present invention is not limited to the following examples unless the gist thereof is exceeded.

Example I Preparation of N-(2-(4-chlorophenoxy)ethyl]=4-chloro-3-ethyl-1-methyl-5-pyrazolecarboxamide 4-chloro-3-ethyl-1-methyl-5-pyrazolecarvone 1.25 g of acid and 2.36 g of thionyl chloride
The mixture was heated to reflux for an hour. After thionyl chloride was distilled off under reduced pressure, the residue was dissolved in 10Ill of toluene to obtain 4-chloro-3-ethyl-1-methyl-5-pyrazolecarboxylic acid chloride. This was added dropwise to a toluene solution 201) 1 containing 1.14 g of 2-(4-chlorophenoxy)ethylamine and 0.74 g of triethylamine at 0 to 10°C. After the dropwise addition, the mixture was stirred for 2 hours, poured into ice water, and extracted with toluene.

The toluene layer was washed with an aqueous sodium carbonate solution, water, and saturated brine. After drying over anhydrous sodium sulfate, it was concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain 2.04 g of the compound (m9) listed in Table 1.

The NMR and IR of this compound were as follows.

'HN M R (CDCl,) δppei;
1.25 (L, 3H).

2.65 (q, 2H), 3.9 (m,
2H), 4.15(s, 3H), 4.05~
4.15 (m, 2H), 6°85 (d, 2H),
7.3 (d, 2H), 7.0~7゜4 (b, IH) IR (KBr) ear-'13270.164.0.1
550, 1490. 1285. 1240 Example 2 N(2-(4-n-pentylphenoxy)ethyl2
-Production of chloro-3-ethyl-1-methyl-5-pyrazolecarboxamide 1.37 g of 4-chloro-3-ethyl-1-methyl-5-pyrazolecarboxylic acid chloride synthesized in Example 1 was
(4-n-pentylphenoxy)ethylamine 1.37
g and triethylamine 0.74 g in ethyl acetate solution 50
The mixture was added dropwise into mff at 0 to 10°C, stirred for 1.5 hours, poured into ice water, and extracted with ethyl acetate. The ethyl acetate layer was washed with an aqueous sodium carbonate solution, water, and saturated brine. After drying over anhydrous sodium sulfate, the mixture was concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain 2.25 g of the compound (patient 6) listed in Table 1.

The NMR and IR of this compound were as follows.

'HN M R(CDC13)δPI)m; 0
．． 9 (t, 3H).

1.1~1.7 (m, 4H), 2.4~2
．． 7 (m, 4H), 3.8 (m, 2H), 4
．． 1 (m, 5H), 6°? (d, 2H),
7.0 (d, 2H), 7.1 (b.

IH) IR(Na(Jam-'; 3420. 2920.
1665, 1530. 1500. 1460. 1
285° 240 Example 3 Production of N-(2-(2,6-dichloro-4-n-pentylphenoxy)ethyl-4-chloro-3-ethyl-1-methyl-5-pyrazole carboxamide) Azodicarboxylic acid diethyl ester 0 .87g was taken in 5ml of tetrahydrofuran, and this was added to N-(2-hydroxyethyl)-4-chloro-3-ethyl-1-methyl-5.
- Add dropwise to a solution of 1.16 g of pyrazole carboxamide, 1.04 g of 2,6-dichloro-4-n-pentylphenol, and 1.31 g of triphenylphosphine in 20 Ill of tetrahydrofuran with stirring at room temperature, and stir the reaction mixture for 4 hours. . Then, the solvent was distilled off, and the remaining oil was purified by silica gel column chromatography.
0.89 g of compound 17I (patient 35) listed in Table 1 was obtained.

The NMR and IR of this compound were as follows.

'HNMR(CDCl3)δppm; 0
．． 90 (m, 3H).

1.1~1.8 (m, 9H), 2.3~2
．． 8 (m, 4H), 3.80 (m, 2H), 4
．． 05 (s, 3H).

4.15 (m, 2H), 7.05 (s,
2H), 7.25 (b, IH) IR(KBr)ell-'; 3400, 2920, 16
60.1530, 1500, 1475, 1455°27
0 Example 4 According to the method of Examples 1 to 3, the compounds listed in Table 1 were obtained.

Table-1 (Part 1) Table-1 (Part 2) Table-1 (Part 3) (Part 4) Table 1 (Part 5) Table-1 (Part 7) Table-1 (Part 6) Table-1 (Part 6) 8) Table-1 (Part 9) Table-1 (Part 10) Next, formulation examples of the compounds of the present invention are shown.
"%" means "parts by weight" and "% by weight", respectively.

Formulation Example 1: 20 parts of the compound of the present invention according to Hydration Table-1, Carplex #80
(Shionogi Pharmaceutical Co., Ltd., trade name) 20 copies, N.

55 parts of N-kaolin clay (Ueya Kaolin Co., Ltd., trade name) and 5 parts of a higher alcohol sulfate ester surfactant Tsurupol 8070 (Toho Chemical Co., Ltd., trade name) were mixed and pulverized uniformly to obtain 40% active ingredient. A hydrating agent containing the following was obtained.

Formulation Example 2: Powder 2 parts of the compound of the present invention shown in Table 1, 93 parts of clay (manufactured by Nippon Talc Co., Ltd.) and 5 parts of white carbon were uniformly mixed and ground to produce a 2% powder.

Formulation Example 3: Emulsion 20 parts of the compound of the present invention in Table 1 was dissolved in a mixed solvent consisting of 35 parts of xylene and 30 parts of dimethylformamide, and the polyoxyethylene surfactant Tsurupol 3005X (Toho Kagaku Co., Ltd., (Trade name) was added to obtain an emulsion containing 20% of the active ingredient.

Formulation example 4: Flowable agent 30 parts of the compound of the present invention listed in Table 1, 8 parts of ethylene glycol mixed in advance, Tsurpol AC30
32 (Toho Chemical Co., Ltd., trade name) 5 parts and xanthan gum 0
．． 1 part was well mixed and dispersed in 56.9 parts of water. Next, this slurry-like mixture was wet-milled using a Dyno Mill (Shinmaru Enterbrise Co., Ltd.) to obtain a stable flowable agent containing 30% of the active ingredient.

Test Example 1 Effect on adult two-spotted spider mites Ten female adult two-spotted spider mites are released onto the leaf disc (diameter 2 cm) of kidney bean leaves. A solution 51) 1 prepared by diluting the compound of the present invention prepared according to the recipe of Formulation Example 1 with water to a predetermined concentration was sprayed onto this using a rotating spray tower (Mizuha Rika type). (
1 part, 2 repetitions. ) 24 hours after treatment, the survival of the adults was investigated and the acaricidal rate (%
) was sought. The results are shown in Table-2. The compound number corresponds to Table-1.

Test Example 2 Effect on eggs of two-spotted spider mites Five female adult two-spotted spider mites are released onto the leaf disc (diameter 2C1) of kidney bean leaves. Eggs were allowed to lay on leaf discs for 20 hours after release, and then adult females were removed. A solution 5II1) prepared by diluting the compound of the present invention prepared according to the formulation of Formulation Example 1 with water to a predetermined concentration was sprayed onto this using a rotary spraying base (Mizuha Rika type).

(1 batch, 2 repetitions.) Five days after the treatment, the number of unhatched eggs and the number of hatched larvae were investigated, and the ovicidal rate (%) was determined. The results are shown in Table-2. Compound numbers correspond to Table-1.

Table 2 (Part 1) Table 3 Table 2 (Part 2) Test Example 3 The concentrations of compounds 11&135, 38, and 42 were varied as shown in Table 3, and the insecticidal and acaricidal effects were investigated.

The results are shown in Table-3. The compound number corresponds to Table-1.

Test Example 4 Effect on brown planthopper larvae Budding rice seedlings are set in a glass cylinder (diameter 3 al, length 17 cm), and five brown planthopper 4th instar larvae are released. to this,
0.5ml of a solution prepared by diluting the compound of the present invention prepared according to the method of Formulation Example 3 with water! A dispersion tower (manufactured by Mizuha Rika)
It was sprayed using.

(1 concentration, 4 repetitions.) 24 hours after treatment, the survival of the larvae was investigated, and the insecticidal rate (%) was determined.
I asked for The results are shown in Table-4.

The compound level corresponds to Table-1.

Test Example 5 Effect on diamondback moth larvae Nine cabbage leaves (5 x 5 aa) were immersed for 1 minute in a solution prepared by diluting the compound of the present invention prepared according to the method of Formulation Example 1 with water. After soaking, air dry and use a plastic cup (diameter 7cI).
I), and five third instar larvae of diamondback moth were released into this.

(1 concentration, 2 repetitions.) Two days after release, the survival of the larvae was investigated, and the insecticidal rate (%) was determined. The results are shown in Table-4.

The compound number corresponds to Table-1.

Table 4 [Effects of the Invention] As is clear from the above examples, the compounds of the present invention have excellent insecticidal and acaricidal effects.

Out teenager wish Reason Man Man mitsubishi long (1 other person)

Claims (2)

[Claims] (1) Pyrazoleamides represented by the following general formula (I). ▲There are mathematical formulas, chemical formulas, tables, etc.▼・・・・・・( I
) (In the above formula, R^1 represents an alkyl group of C_1 to C_4, R^2 represents a hydrogen atom, an alkyl group of C_1 to C_4, or an alkoxy group of C_1 to C_4, and X is a hydrogen atom, a halogen atom, C_1 to C_4 alkyl group, C_1
~ represents an alkoxy group of C_4 or a haloalkoxy group of C_1 to C_3, and R^2 and X together represent the ▲ formula,
There are chemical formulas, tables, etc. ▼ or ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (However, R^4 is a hydrogen atom or C_1
~C_3 represents an alkyl group. ), R^3 are each independently a hydrogen atom, a halogen atom, an alkyl group of C_1 to C_7, an alkenyl group of C_3 to C_5, or a C_3 to C_
5 alkynyl group, C_3 to C_6 cycloalkyl group, C_1 to C_4 alkoxy group, C_1 to C_4 haloalkoxy group, trifluoromethyl group, nitro group, cyano group, phenyl group, phenoxy group, C_2 to C_5 alkyl group A carbonyl group, an alkoxycarbonyl group of C_2 to C_5, a trimethylsilyl group, an alkylthio group of C_1 to C_4, or adjacent R^3 may be combined to form ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (
However, R^5 and R^6 each independently represent a hydrogen atom or an alkyl group of C_1 to C_4. ). m represents 1, 2 or 3; n represents 1, 2, 3 or 4; ) (2) An insecticide or acaricide containing the pyrazoleamide according to claim 1 as an active ingredient.