JPH0539253A - Hydrazine-based compound, its production and harmful animal controlling agent containing the same compound - Google Patents

Abstract

PURPOSE:To obtain a new hydrazine-based compound showing highly controlling activity against harmful animals. CONSTITUTION:A compound shown by formula I [A is (substituted) benzophenyl, (substituted), quinolynyl, (substituted) benzothienyl, (substituted) thienothienyl, (substituted), tetrahydrobenzothienyl, (substituted) indanyl or (substituted) hexahydroindanyl; W is H, cyano, COCOOR', S-N-(R'')COOR' or CH2COR' (R' and R'' are alkyl or cycloalkyl); R is halogen, (halogenated) alkyl, nitro, etc.; (n) is 0-5] such as N'-t-butyl-N'-3,5-dimethylbenzoyl-N-benzo [b] thiophene-2- carbohydrazide. The compound shown by formula I wherein W is H is obtained by reacting a compound shown by formula II with a compound shown by formula III (X is halogen, alkoxy, etc.).

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to novel hydrazine compounds, a method for producing them and a pest control agent containing them.

[0002]

2. Description of the Related Art As hydrazine compounds, it is known that they are useful as an active ingredient of insecticides according to the respective publications such as JP-A-63-23866 and JP-A-63-83063. However, the hydrazine compounds disclosed in the above publication and the compounds of the present invention are different in the portion A in the general formula (I) described below. The present invention has been completed based on the finding that a specific hydrazine compound exhibits high pesticidal activity.

[0003]

DISCLOSURE OF THE INVENTION The present invention relates to a hydrazine compound represented by the following general formula (I) or a salt thereof, a process for producing them and a pest control agent containing them. General formula (I)

[0004]

[Chemical 1] (In the formula, A is an optionally substituted benzofuranyl group, an optionally substituted quinolinyl group, an optionally substituted benzothienyl group, an optionally substituted benzothiazolyl group, an optionally substituted thienothienyl group, and a substituted A dihydrothienothienyl group which may be substituted, a dihydrocyclopentathienyl group which may be substituted, a tetrahydrobenzothienyl group which may be substituted, an indanyl group which may be substituted or a hexahydroindanyl group which may be substituted, W Is a hydrogen atom, a cyano group, a -COCOOR 'group, -SN
(R ″) COOR ′ group or —CH ₂ OCOR ′ group, R ′ and R ″ are each independently an alkyl group or a cycloalkyl group, and R is a halogen atom or an alkyl optionally substituted with a halogen atom. A group, an alkoxy group which may be substituted with a halogen atom, an alkylthio group which may be substituted with a halogen atom or a nitro group, and n is an integer of 0 to 5, provided that when n is 2 or more, R is May be the same or different).

In the above general formula (I), a benzofuranyl group which may be substituted, a quinolinyl group which may be substituted, a benzothienyl group which may be substituted, a benzothiazolyl group which may be substituted, or a substituent which is substituted Optionally thienothienyl group, optionally substituted dihydrothienothienyl group, optionally substituted dihydrocyclopentathienyl group, optionally substituted tetrahydrobenzothienyl group,
As the substituent of the optionally substituted indanyl group or the optionally substituted hexahydroindanyl group, for example, a halogen atom, an alkyl group optionally substituted with a halogen atom, an alkoxy group optionally substituted with a halogen atom, Examples thereof include an alkylthio group and a nitro group which may be substituted with a halogen atom, and the number thereof may be 1 or 2 or more. The halogen atom contained in A and R includes, for example, a fluorine atom, a chlorine atom, a bromine atom and an iodine atom, and the alkyl group and the alkyl moiety contained in A, R, R ′ and R ″ are carbon atoms. Examples include those having a number of 1 to 6, such as a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, and a hexyl group, which are straight-chain or branched fatty chains such as an isopropyl group and a tert-butyl group. Structural cycloisomers are also included. The cycloalkyl group contained in R ′ and R ″ has a carbon number of 3 to 6, such as cyclopropyl group, cyclobutyl group, cyclopentyl group,
A cyclohexyl group may be mentioned.

In the general formula (I), benzofuranyl group which may be substituted, quinolinyl group which may be substituted, benzothienyl group which may be substituted, benzothiazolyl group which may be substituted, and Optionally thienothienyl group, optionally substituted dihydrothienothienyl group, optionally substituted dihydrocyclopentathienyl group, optionally substituted tetrahydrobenzothienyl group,
In the optionally substituted indanyl group or the optionally substituted hexahydroindanyl group, when the number of substituents is 2 or more, they may be the same or different.
When _n of (R) _n is 2 or more, R may be the same or different.

Of the compounds represented by the general formula (I), those in which W is a hydrogen atom may be salts with basic substances, such as ammonium salts, alkali metal salts and alkaline earth metal salts. Can be mentioned. Examples of the alkali metal salt include sodium salt, potassium salt, lithium salt and the like, and examples of the alkaline earth metal salt include calcium salt, magnesium salt, barium salt and the like.

In the compound represented by the general formula (I),
A is an optionally substituted benzothienyl group, an optionally substituted thienothienyl group, an optionally substituted dihydrocyclopentathienyl group or an optionally substituted tetrahydrobenzothienyl group, W is a hydrogen atom, and R is Is a halogen atom or an alkyl group, and n is 1 or 2, and among these desirable compounds, A is a benzothienyl group which may be substituted, a dihydrocyclopentathienyl group which may be substituted, or a substituent. It is more desirable that it is a tetrahydrobenzothienyl group which may be substituted, and among these more desirable compounds, N′-t-butyl-N′-3,5-dimethylbenzoyl-N-benzo [b] thiophene-2- Carbohydrazide (Compound No. 5 described below), N'-t-butyl-N'-3,5-dimethylbenzoyl-N-5, 6-dihydro-4H-cyclopenta [b] thiophene-2-carbohydrazide (Compound No. 34 described below), N'-t-butyl-N'-3,5-
Dimethylbenzoyl-N-4,5,6,7-tetrahydrobenzo [b] thiophene-2-carbohydrazide (Compound No. 35 described later) is the most desirable.

Among the compounds represented by the general formula (I), those in which W is a hydrogen atom can be produced, for example, by the method of the following reaction step a. [Reaction step a]

[0010]

[Chemical 6] {In the formula, A, R and n are as described above, and X is a halogen atom, an alkoxy group or a -OCOT group (T is an alkyl group)}

Reaction step a is usually carried out in the presence of a solvent and a base. Solvents include water; aromatic hydrocarbons such as benzene and toluene; ethers such as diethyl ether and tetrahydrofuran; halogenated hydrocarbons such as methylene chloride and chloroform; acetonitrile, dimethylformamide, pyridine and the like. Solvents inert to the reaction such as an aprotic polar solvent can be mentioned, and these can be used alone or as a mixture, and a mixed solvent of water and toluene or a mixed solvent of water and methylene chloride is particularly desirable. As the base, a tertiary amine such as triethylamine; an alkali metal hydroxide such as sodium hydroxide or potassium hydroxide; sodium carbonate,
Examples thereof include alkali metal carbonates such as potassium carbonate; alkoxides such as sodium methoxide and sodium ethoxide; pyridine and the like, and sodium hydroxide is particularly preferable. Of these, pyridine, which is a base and can be used as a solvent at the same time, is also preferable. The reaction temperature is usually -50 ° C to + 100 ° C, preferably 0 ° C to 30 ° C when X in the compound represented by the general formula (III) is a halogen atom or a -OCOT group, and X is an alkoxy group. In the case, it is 50 ° C to 100 ° C. The reaction time is usually 0.1 to 24 hours, preferably 0.5 to 3 hours.

The compound represented by the general formula (II) can be produced, for example, by the method of the following reaction step b. [Reaction step b]

[0013]

[Chemical 7] (In the formula, A is as described above, and Y is a halogen atom or an alkoxy group.)

Examples of the solvent used in the reaction step b include the solvents that can be used in the reaction step a, and alcohols such as methanol and ethanol. These can be used alone or as a mixture, and particularly, Methanol or a mixed solvent of water and toluene is desirable. As the base used in the reaction step b, the same bases as those usable in the reaction step a can be mentioned, and among them, sodium hydroxide and sodium methoxide are preferable. The reaction temperature in the reaction step b is usually −20 ° C. to + 100 ° C., preferably 0 ° C. to 50 ° C. when Y in the compound represented by the general formula (IV) is a halogen atom, and 80 ° C. when Y is an alkoxy group. ~ 100 ° C. Reaction time is usually 0.1
24 hours, preferably 0.5 to 5 hours.

Further, the compound represented by the general formula (IV) is described in, for example, J. Org. Chem, vol. 21,
39-44 (1956), J. Chem. Soc. C,
It can be produced by the following reaction steps cd using the general formula (V) described below, which can be produced by the method described in 1225 to 1227 (1968), as a raw material. [Reaction step c]

[0016]

[Chemical 8] [Reaction step d]

[0017]

[Chemical 9] (In the formula, A is as described above, Z ¹ is a halogen atom, and Z ² is an alkyl group.)

Examples of the halogenating agent in the reaction step c include thionyl chloride, phosphorus oxychloride, thionyl bromide and the like. In the reaction step d, the base includes a tertiary amine such as triethylamine; pyridine and the like, and the solvent includes the solvent used in the reaction step a other than water.

Next, an example of a specific synthesis example of the compound of the present invention in which W is a hydrogen atom will be described. Synthesis Example 1 Synthesis of N'-t-butyl-N'-3,5-dimethylbenzoyl-N-benzo [b] thiophene-2-carbohydrazide (Compound No. 5 described later) (1) Benzo [b] thiophene- 2-carboxylic acid 1.0
After reacting g with 2 ml of thionyl chloride under reflux overnight,
Excess thionyl chloride was distilled off under reduced pressure to obtain benzo [b] thiophene-2-carbonyl chloride as a solid.

1.4 g of Nt-butylhydrazine hydrochloride
Is dissolved in 15 ml of methanol to give 28% under ice cooling.
After 2.2 g of a sodium methoxide methanol solution was added dropwise and the mixture was stirred at the same temperature for 15 minutes, 2 ml of the benzo [b] thiophene-2-carbonyl chloride methylene chloride solution was gradually added. After reacting at the same temperature for 1 hour with stirring, the reaction mixture was put into water and extracted with ethyl acetate. Then, the organic layer was washed with water, anhydrous sodium sulfate was added, and the organic layer was dried. Then, the crude product obtained by distilling off the solvent under reduced pressure was purified by silica gel column chromatography (eluent: methylene chloride / ethyl acetate = 2/1) to give N′-having a melting point of 147 to 148 ° C. t-butyl-
1.1 g of N-benzo [b] thiophene-2-carbohydrazide (intermediate body No. 5 described later) was obtained. (2) N'-t-butyl-N obtained in the step (1)
-Benzo [b] thiophene-2-carbohydrazide 30
In a solution of 0 mg dissolved in 3 ml of pyridine under ice cooling,
220 mg of 5-dimethylbenzoyl chloride was added dropwise. After reacting at the same temperature for 1 hour with stirring, the reaction mixture was put into water and extracted with ethyl acetate. Then, the organic layer was washed with water, anhydrous sodium sulfate was added, and the organic layer was dried. Next, the crude product obtained by distilling off the solvent under reduced pressure is purified by silica gel column chromatography (eluent: methylene chloride / ethyl acetate = 95/5) to give the desired compound having a melting point of 211-213 ° C. (see below). Compound No. 5) 40
0 mg was obtained.

Synthesis Example 2 N'-t-butyl-N'-3,
Synthesis of 5-dimethylbenzoyl-N-6-fluorobenzo [b] thiophene-2-carbohydrazide (Compound No. 22 described later) (1) In a solution prepared by suspending 10.8 g of rhodanine and 20 g of sodium acetate in 100 ml of acetic acid. At room temperature, 10 g of 4-fluorobenzaldehyde was added dropwise. The resulting mixture was reacted under reflux for 2 hours and then cooled to room temperature. Next, this reaction mixture was poured into about 500 ml of water, and the obtained solid matter was filtered, washed with water, and dried to give 5- (4-
16.4 g of fluorobenzylidene) rodanine was obtained. (2) 10 g of 5- (4-fluorobenzylidene) rhodanine obtained in the above step (1) in a solution obtained by dissolving 8.3 g of sodium hydroxide in 700 ml of water and then heating to about 70 ° C.
Was added, and the mixture was reacted at the same temperature for 20 minutes with stirring. After the reaction is completed, the reaction solution is cooled to 10 ° C. or lower and concentrated hydrochloric acid 20 m
1 was added dropwise. The solid matter was filtered, washed with water, and dried to obtain 6.1 g of 3- (4-fluorophenyl) -2-mercaptoacrylic acid.

(3) 12 g of iodine and 80 m of nitrobenzene
In a solution obtained by heating the mixture of 1 to about 190 ° C., the 3- (4-fluorophenyl) -2-obtained in the step (2) was obtained.
1.5 g of mercaptoacrylic acid was added, and the mixture was reacted for 2 minutes with stirring. After completion of the reaction, the reaction solution was cooled to room temperature and extracted with 100 ml of 1% sodium hydroxide aqueous solution. After adding an appropriate amount of sodium hydrogen sulfite to the extract,
Concentrated hydrochloric acid was added dropwise to adjust the pH to 1. After filtering the precipitate,
Washed with water, then hexane, dried to give 6-fluorobenzo [b] thiophene-2-carboxylic acid 910 m.
g was obtained. (4) After reacting 700 mg of 6-fluorobenzo [b] thiophene-2-carboxylic acid obtained in the above step (3) with 2 ml of thionyl chloride under reflux overnight, excess thionyl chloride was distilled off under reduced pressure. Then 6-fluorobenzo [b]
Obtained thiophene-2-carbonyl chloride.

Nt-butylhydrazine hydrochloride 900 m
28% in a solution prepared by dissolving g in 9 ml of methanol under ice cooling.
After 1.4 g of a sodium methoxide methanol solution was added dropwise and stirred at the same temperature for 15 minutes, 2 ml of a methylene chloride solution of 6-fluorobenzo [b] thiophene-2-carbonyl chloride was gradually added. After reacting at the same temperature for 1 hour with stirring, the reaction mixture was put into water and extracted with ethyl acetate. After that, the organic layer was washed with water, and anhydrous sodium sulfate was added and dried. Next, the crude product obtained by distilling off the solvent under reduced pressure was subjected to silica gel column chromatography (eluent: methylene chloride / ethyl acetate = 2/1).
N′-t having a melting point of 175 to 176 ° C.
-Butyl-N-6-fluorobenzo [b] thiophene-
2-Carbohydrazide (intermediate body No. 16 described below) 720
mg was obtained. (5) N'-t-butyl-N obtained in the step (4)
A solution of 300 mg of -6-fluorobenzo [b] thiophene-2-carbohydrazide dissolved in 3 ml of pyridine was cooled with ice to give 210 m of 3,5-dimethylbenzoyl chloride.
0.5 ml of a methylene chloride solution containing g was added dropwise. After reacting at the same temperature for 1 hour with stirring, the reaction mixture was put into water and extracted with ethyl acetate. Then, the organic layer was washed with water, anhydrous sodium sulfate was added, and the organic layer was dried. Then, the solvent was distilled off under reduced pressure, and the obtained crude product was purified by silica gel column chromatography (eluent: methylene chloride / ethyl acetate = 95/5) to give a melting point of 243-2.
420 mg of the desired product (compound No. 22 described later) at 44 ° C. was obtained.

Synthesis Example 3 N'-t-butyl-N'-3,
5-Dimethylbenzoyl-N-5,6-dihydro-4H
-Synthesis of cyclopenta [b] thiophene-2-carbohydrazide (Compound No. 34 described later) (1) 1.0 g of 5,6-dihydro-4H-cyclopenta [b] thiophene-2-carboxylic acid was added to 4 m of thionyl chloride.
After reacting with 1 under reflux for 3.5 hours, excess thionyl chloride was distilled off under reduced pressure to obtain 5,6-dihydro-4H-cyclopenta [b] thiophene-2-carbonyl chloride. To a solution of 1.48 g of Nt-butylhydrazine hydrochloride dissolved in 17 ml of methanol was added 2.41 g of 28% sodium methoxide methanol solution under ice cooling, and the mixture was stirred at the same temperature for 30 minutes, and then the above 5,6. -Dihydro-4H
A solution of cyclopenta [b] thiophene-2-carbonyl chloride in 7 ml of methylene chloride was gradually added. After reacting at the same temperature for 1 hour with stirring, the reaction mixture was put into water and extracted with ethyl acetate. Then, the organic layer was washed with water, anhydrous sodium sulfate was added, and the organic layer was dried. Next, the solvent was distilled off under reduced pressure, and the crude product obtained was purified by silica gel column chromatography (eluent: methylene chloride / ethyl acetate = 3/1) to give a melting point of 1
There was obtained 0.86 g of N'-t-butyl-N-5,6-dihydro-4H-cyclopenta [b] thiophene-2-carbohydrazide (after-mentioned intermediate No. 28) at 63 to 164 ° C.

(2) N'-t obtained in the step (1)
-Butyl-N-5,6-dihydro-4H-cyclopenta [b] thiophene-2-carbohydrazide 700 mg dissolved in a solution of pyridine 9 ml, 3,5-dimethylbenzoyl chloride 544 mg was added to a methylene chloride solution 2 ml under ice cooling. The dissolved solution was added dropwise. After reacting for 1.5 hours at the same temperature, the reaction mixture was put into water and extracted with ethyl acetate. Then, the organic layer was washed with water, anhydrous sodium sulfate was added, and the organic layer was dried. Next, the crude product obtained by distilling off the solvent under reduced pressure is purified by silica gel column chromatography (eluent: methylene chloride / ethyl acetate = 95/5) to give the desired product having a melting point of 231 to 232 ° C. (see below). 0.88 g of compound No. 34) was obtained.

Synthesis Example 4 N'-t-butyl-N'-3,
Synthesis of 5-dimethylbenzoyl-N-4,5,6,7-tetrahydrobenzo [b] thiophene-2-carbohydrazide (Compound No. 35 described below) (1) 4,5,6,7-tetrahydrobenzo [b ] 1.0 g of thiophene-2-carboxylic acid 4 ml of thionyl chloride
After reacting for 3.5 hours under reflux, excess thionyl chloride was distilled off under reduced pressure to obtain 4,5,6,7-tetrahydrobenzo [b] thiophene-2-carbonyl chloride. To a solution prepared by dissolving 1.37 g of Nt-butylhydrazine hydrochloride in 16 ml of methanol, 2.22 g of 28% sodium methoxide methanol solution was added dropwise under ice cooling, and the mixture was stirred at the same temperature for 30 minutes, and then 4, 5 A solution of 7,6,7-tetrahydrobenzo [b] thiophene-2-carbonyl chloride in 7 ml of methylene chloride was gradually added. After reacting at the same temperature for 1 hour with stirring, the reaction mixture was put into water and extracted with ethyl acetate. Then, the organic layer was washed with water, anhydrous sodium sulfate was added, and the organic layer was dried. Then, the crude product obtained by distilling off the solvent under reduced pressure was purified by silica gel column chromatography (eluent: methylene chloride / ethyl acetate = 3/2) to give a melting point of 1
N'-t-butyl-N-4,5,6, 55-157 ° C
0.72 g of 7-tetrahydrobenzo [b] thiophene-2-carbohydrazide (intermediate body No. 29 described later) was obtained.

(2) N'-t obtained in the above step (1)
-Butyl-N-4,5,6,7-tetrahydrobenzo [b] thiophene-2-carbohydrazide 700 mg dissolved in a solution of pyridine 8 ml, 3,5-dimethylbenzoyl chloride 512 mg under methylene chloride solution 2 ml methylene chloride solution 2 ml. The solution dissolved in was added dropwise. After reacting for 1.5 hours at the same temperature, the reaction mixture was put into water and extracted with ethyl acetate. Then, the organic layer was washed with water, anhydrous sodium sulfate was added, and the organic layer was dried. Next, the crude product obtained by distilling off the solvent under reduced pressure is purified by silica gel column chromatography (eluent: methylene chloride / ethyl acetate = 95/5) to give the desired product having a melting point of 243 to 244 ° C. (described later). Compound No. 35) 0.96g was obtained.

The compounds represented by the above general formulas (II), (IV) and (V) as intermediates of the compound of the present invention include novel compounds, representative examples of which are shown in Table 1-1 to Table 1 below. See Table 1-3.

[0029]

[Table 1]

[0030]

[Table 2]

[0031]

[Table 3]

[0032]

[Table 4]

[0033]

[Table 5]

[0034]

[Table 6]

Next, among the compounds of the present invention represented by the above general formula (I), typical examples of those in which W is a hydrogen atom are described in the second section below.
List in the table.

[0036]

[Table 7]

[0037]

[Table 8]

[0038]

[Table 9]

[0039]

[Table 10]

[0040]

[Table 11]

[0041]

[Table 12]

In the above general formula (I), the compound represented by the following general formula (I-2) having an appropriate substituent on the nitrogen atom having a hydrogen atom at the hydrazine site also exhibits high pesticidal activity. ..

[0043]

[Chemical 5]

Where A, R and n are as described above,
W'is a cyano group, -COCOOR 'group, -SN
(R ") COOR 'group or a _-CH 2 OCOR' group (R '
And R ″ are as described above).

The compound represented by the general formula (I-2) can be produced, for example, by the following production method or European Patent Publication No. 039.
5581, European Patent Publication No. 0398842,
U.S. Pat. No. 4,857,550, JP-A-2-207066.
It can be manufactured according to the method described in No. (I-1) + W'-G-> (I-2) (W 'is as above-mentioned, G is a chlorine atom or a bromine atom.) The above reaction is usually performed in the presence of a solvent and a base at a reaction temperature- 100 to + 150 ° C, preferably -80 to +10
0 ° C., reaction time 0.1 to 24 hours, preferably 0.2 to
It takes 3 hours. As the solvent, aromatic hydrocarbons such as benzene and toluene; ethers such as diethyl ether and tetrahydrofuran; aprotic polar solvents such as acetonitrile, dimethylformamide, dimethylsulfoxide, hexamethylphosphoric triamide, etc. Active solvents are mentioned, and these can be used alone or as a mixture. Further, as the base, an inorganic base such as sodium hydride or potassium hydride; n-
It is appropriately selected from organic lithium compounds such as butyl lithium, tert-butyl lithium and phenyl lithium, organic bases such as triethylamine and pyridine, and the like.

Next, an example of a specific synthesis example of the compound of the present invention in which W is W '(W' is as described above) will be described. Synthesis Example 5 N'-t-butyl-N-cyano-N'-3,
5-Dimethylbenzoyl-N-5,6-dihydro-4H
-Cyclopenta [b] thiophene-2-carbohydrazide (Compound No. 61)

500 mg of N'-t-butyl-N'-3,5-dimethylbenzoyl-N-5,6-dihydro-4H-cyclopenta [b] thiophene-2-carbohydrazide (the above compound No. 34) was added to tetrahydrofuran. 5m
To a solution of 1 and 1 ml of hexamethylphosphoric triamide dissolved in a mixed solvent, 80 mg of a 60% sodium hydride mineral oil dispersion was gradually added. After addition, the reaction solution is allowed to stand at room temperature for 15
After stirring for 1 minute, 240 mg of cyanogen bromide was added and the mixture was reacted under reflux for 1 hour.

After completion of the reaction, the reaction solution was cooled to room temperature,
The reaction product was put into water and extracted with ethyl acetate. afterwards,
The organic layer was washed with water, dried over anhydrous sodium sulfate. Next, the solvent was distilled off under reduced pressure, and the crude product obtained was purified by silica gel column chromatography (eluent: n-hexane / ethyl acetate = 9/1) to obtain a refractive index of 1.5631 (20. 6 ° C target product (Compound N)
o. 61) 310 mg was obtained.

The compounds obtained by the production method according to the above synthesis examples are described below. Compound No. 62: N'-t-butyl-N'-3,5-dimethylbenzoyl-N-ethoxalyl-N-5,6-dihydro-4H-cyclopenta [b]
Thiophene-2-carbohydrazide (refractive index 1.5412 (46.4 ° C.)) Compound No. 63: N'-t-butyl-N'-3,5-
Dimethylbenzoyl-N-[(N "-methyl-N" -n
-Butoxycarbonyl) aminosulfenyl] -N-
5,6-Dihydro-4H-cyclopenta [b] thiophene-2-carbohydrazide (viscous oil)

The compound of the present invention represented by the above general formula (I) exhibits excellent activity as an active ingredient of a pest controlling agent. For example, phytoseiid mites, spoilage mites, citrus mites, phytoseiid mites, mosquito mites, etc., diamondback moth, weevil, common worm, codling moth, ball worms, tobacco bad worms, gypsy moths, cobb nome moth,
Chacodon beetle, Colorado potato beetle, sorghum beetle, boleweville, aphids, planthoppers, leafhoppers, scale insects, stink bugs, whiteflies,
Thrips, grasshoppers, sand flies, scarabs,
Agricultural pests such as Tamanagaga, Kaburigaga, ants, etc., sanitary pests such as house dust mites, cockroaches, house flies, and Culex pipiens, storage pests such as Bakuga, Azuki bean weevils, Kokunusutomodoki, Gomudida, etc. It is also effective against clothing such as scutellaria beetle and termites, house pests, and fleas, lice and flies parasitic on livestock. It is also effective against soil pests. Examples of soil pests referred to here include gastropods such as slugs and snails, and isopods such as pill bugs and wallworms.
Among the above-mentioned various pests, it exhibits an excellent activity against lepidopteran pests. It is also effective against insect pests such as Plutella xylostella and housefly which are resistant to organophosphorus agents and pyrethroids. Further, since it has a systemic migration property, the compound of the present invention is applied to the soil to control soil harmful insects, mites, nematodes, gastropods, isopods, and at the same time pests of foliage. Can also be controlled. In addition, it has high safety against mammals, fish, and beneficial insects, and has good properties as a pest control agent.

When the compound of the present invention is used as an active ingredient of a pest control agent, emulsions, powders, granules, wettable powders, granule wettable powders, together with pesticide adjuvants are used as in the case of conventional pesticide formulations. It can be formulated in various forms such as suspensions, aerosols and pastes. The mixing ratio of these is usually 0.1 to 90 parts by weight of the active ingredient, preferably 0.5 to
90 parts by weight, more preferably 0.5 to 80 parts by weight, and 10 to 99.9 parts by weight, preferably 10 to 99.9 parts by weight of the agricultural chemical adjuvant.
It is 99.5 parts by weight, and more preferably 20 to 99.5 parts by weight. In the actual use of these preparations, they can be used as they are or diluted with a diluent such as water to a predetermined concentration and used.

Examples of the agricultural chemicals auxiliary agent include carriers, emulsifiers, suspending agents, dispersing agents, spreading agents, penetrating agents, wetting agents, thickening agents, defoaming agents, stabilizers, antifreezing agents and the like. However, it may be added as needed. The carrier is divided into a solid carrier and a liquid carrier, and as the solid carrier, starch, activated carbon, soybean flour, wheat flour, wood flour, fish meal, powdered animal or vegetable powder such as milk powder, talc, kaolin, bentonite, calcium carbonate, zeolite, Diatomaceous earth, white carbon, clay,
Mineral powders such as alumina, sulfur powder, anhydrous sodium sulfate and the like can be mentioned, and as the liquid carrier, water, alcohols such as methyl alcohol and ethylene glycol, ketones such as acetone, methyl ethyl ketone and N-methyl-2-pyrrolidone. , Ethers such as dioxane and tetrahydrofuran, aliphatic hydrocarbons such as kerosene,
Aliphatic hydrocarbons such as xylene, trimethylbenzene, tetramethylbenzene, cyclohexane, solvent naphtha, halogenated hydrocarbons such as chloroform and chlorobenzene, acid amides such as dimethylformamide, ethyl acetate, fatty acid glycerin ester, etc. Esters, nitriles such as acetonitrile,
Examples thereof include sulfur-containing compounds such as dimethyl sulfoxide, vegetable oils such as soybean oil and corn oil.

Next, formulation examples of the pest control agent containing the compound of the present invention as an active ingredient will be described, but the types, blending ratios, dosage forms, etc. of the active ingredient compound and the agricultural chemical adjuvant are limited only to the described examples. Not something. Formulation Example 1 (1) Compound No. 5: 20 parts by weight (2) Kaolin: 52 parts by weight (3) Sodium lignin sulfonate: 8 parts by weight (4) White carbon: 20 parts by weight The above ingredients are uniformly mixed to obtain a wettable powder. Formulation Example 2 (1) Compound No. 34 ... 5 parts by weight (2) Talc ... 95 parts by weight The above ingredients are uniformly mixed to obtain a powder. Formulation Example 3 (1) Compound No. 35: 20 parts by weight (2) N-methyl-2-pyrrolidone: 10 parts by weight (3) Polyoxyethylene alkylphenyl ether:
10 parts by weight (4) Xylene ... 60 parts by weight The above ingredients are uniformly mixed and dissolved to obtain an emulsion.

Formulation Example 4 (1) Kaolin: 83 parts by weight (2) Sodium lignin sulfonate: 2 parts by weight (3) Polyoxyethylene alkylaryl sulphate: 5 parts by weight (4) Fine silica: 10 parts by weight Each of the above Mixture of components and compound no. 17 and 4 are mixed at a polymerization ratio of 4: 1 to obtain a wettable powder. Formulation Example 5 (1) Compound No. 34 ... 40 parts by weight (2) Oxidized polyalkylphenol phosphate-triethanolamine ... 2 parts by weight (3) Silicone ... 0.2 parts by weight (4) Zansan gum ... 0.1 parts by weight (5) Ethylene glycol ... 5 Parts by weight (6) Water ... 52.7 parts by weight The above components are uniformly mixed and ground to give an aqueous suspension. Formulation Example 6 (1) Compound No. 5: 75 parts by weight (2) Sodium polycarboxylate: 13.5 parts by weight (3) Anhydrous sodium sulfate: 10 parts by weight (4) Dextrin: 0.5 parts by weight (5) Sodium alkylsulfonate: 1 part by weight or more Put each of the ingredients in a high-speed mixing granulator, and then add 20
% Of water is added, and the mixture is granulated and dried to obtain a granular wettable powder.

Formulation Example 7 (1) Compound No. 22 ... 5 parts by weight (2) Bentonite ... 33 parts by weight (3) Kaolin ... 57 parts by weight (4) Sodium lignin sulfonate ... 5 parts by weight An appropriate amount of water required for granulation is added to each of the above components, and the mixture is granulated Granules are obtained. Formulation Example 8 (1) Compound No. 24 ... 2.5 parts by weight (2) N-methyl-2-pyrrolidone ... 2.5 parts by weight (3) Soybean oil ... 95.0 parts by weight The above materials are uniformly mixed and dissolved to form a trace amount spraying agent (ult).
ra low volume formatulatio
n). Formulation Example 9 (1) Compound No. 30 ... 5 parts by weight (2) N-methyl-2-pyrrolidone ... 5 parts by weight (3) Polyoxyethylene alkylaryl ether ...
10 parts by weight (4) Xylene ... 80 parts by weight The above components are uniformly mixed to obtain an emulsion.

Formulation Example 10 (1) Compound No. 43 ... 10 parts by weight (2) Corn oil ... 77 parts by weight (3) Polyoxyethylene hydrogenated castor oil ... 12 parts by weight (4) Organic bentonite ... 1 part by weight The above are uniformly mixed and pulverized to obtain an oily suspension. An agent is obtained.

Further, the pest controlling agent containing the compound of the present invention as an active ingredient is, if necessary, other pesticides such as insecticides, acaricides, nematicides, fungicides, antiviral agents,
It can be mixed and used in combination with an attractant, a herbicide, a plant growth regulator and the like, and in this case, a more excellent effect may be exhibited.

For example, as an insecticide, acaricide or nematicide, O- (4-bromo-2-chlorophenyl)
O-ethyl S-propyl phosphorothioate, O-
(2,2-Dichlorovinyl) O, O-dimethyl phosphate, O-ethyl O- [3-methyl-4- (methylthio) phenyl] N-isopropyl phosphoramidate, O, O-dimethyl O- (4- Nitro-m-tolyl) phosphorothioate, O-ethyl O- (4-nitrophenyl) phenylphosphonothioate, O, O-diethyl O- (2-isopropyl-6-methylpyrimidin-4-yl) phosphorothioate, O, O -Dimethyl O- (3,5,6-trichloro-2-pyridyl) phosphorothioate, O, S-dimethyl N-acetylphosphoramidothioate, O- (2,4-dichlorophenyl) O-ethyl S-propylphosphoro Dithioate, (RS) -S-sec-butyl O-ethyl 2-
Organophosphate compounds such as oxo-1,3-thiazolidin-3-ylphosphonothioate; 1-naphthyl N-methylcarbamate, 2-isopropoxyphenyl N-methylcarbamate, 2-methyl-2-
(Methylthio) propionaldehyde O-methylcarbamoyl oxime, 2,3-dihydro-2,2-dimethylbenzofuran-7-yl N-methylcarbamate,
Dimethyl N, N '-[thiobis {(methylimino) carbonyloxy}] bisethaneimidothioate, S-
Methyl N- (methylcarbamoyloxy) thioacetimidate, N, N-dimethyl-2-methylcarbamoyloxyimino-2- (methylthio) acetamide, 2
-(Ethylthiomethyl) phenyl N-methylcarbamate, 2-dimethylamino-5,6-dimethylpyrimidin-4-yl N, N-dimethylcarbamate, 2-s
Carbamate compounds such as ec-butylphenyl N-methylcarbamate; S, S'-2-dimethylaminotrimethylene bis (thiocarbamate), N, N-dimethyl-1,2,3-trithian-5-ylamine Nereistoxin derivatives such as 2,2,2-trichloro-1,1-bis (4-chlorophenyl) ethanol, 4
-Organochlorine compounds such as chlorophenyl-2,4,5-trichlorophenyl sulfone; bis [tris (2-
Methyl-2-phenyl-propyl) tin] oxide, an organometallic compound; (RS) -α-cyano-3-phenoxybenzyl (RS) -2- (4-chlorophenyl) -3-methylbutyrate, 3 -Phenoxybenzyl (1RS) -cis, trans-3- (2,2-dichlorovinyl) -2,2-dimethylcyclopropanecarboxylate, (RS) -α-cyano-3-phenoxybenzyl (1RS) -cis, Trans-3- (2,2-dichlorovinyl) -2,2-dimethylcyclopropanecarboxylate, (S) -α-cyano-3-phenoxybenzyl (1R) -cis-3- (2,2-dibromovinyl ) −
2,2-dimethylcyclopropanecarboxylate,
(RS) -α-cyano-3-phenoxybenzyl (1R
S) -cis, trans-3- (2-chloro-3,3,3
-Trifluoropropenyl) -2,2-dimethylcyclopropanecarboxylate, 4-methyl-2,3,5
6-tetrafluorobenzyl-3- (2-chloro-3,
3,3-trifluoro-1-propenyl) -2,2-dimethylcyclopropanecarboxylate, 2- (4-ethoxyphenyl) -2-methylpropyl 3-phenoxybenzyl ether (generic name-ethofenprox.
Compound No. Pyrethroid compounds such as A-1); 1- (4-chlorophenyl) -3- (2,6)
-Difluorobenzoyl) urea, 1- [3,5-dichloro-4- (3-chloro-5-trifluoromethyl-2)
-Pyridyloxy) phenyl] -3- (2,6-difluorobenzoyl) urea, 1- (3,5-dichloro-
Benzoyl urea compounds such as 2,4-difluorophenyl) -3- (2,6-difluorobenzoyl) urea; isopropyl (2E, 4E) -11-methoxy-3,7,11-trimethyl-2,4- Juvenile hormone-like compounds such as dodecadienoate; 2-t-butyl-
5- (4-t-butylbenzylthio) -4-chloro-3
Pyridazinone compounds such as (2H) -pyridazinone; pyrazole compounds such as t-butyl 4-[(1,3-dimethyl-5-phenoxypyrazol-4-yl) methyleneaminooxymethyl] benzoate; 1-
(6-chloro-3-pyridylmethyl) -N-nitro-imidazolidine-2-ylideneamine (generic name: imidacloprid, hereinafter abbreviated as compound No. A-2), 1- [N
-(6-Chloro-3-pyridylmethyl) -N-ethylamino] -1-methylamino-2-nitroethylene (European publication No. 302389, hereinafter compound No. A-
3), 2-methylamino-2- [N-methyl-N
-(6-Chloro-3-pyridylmethyl) amino] -1-
Nitroethylene (European publication No. 302389,
Compound No. Abbreviated as A-4), 1- (6-chloro-
3-pyridylmethyl) amino-1-dimethylamino-2
-Nitroethylene (European publication No. 30238
9, hereinafter compound No. Abbreviated as A-5), 1- (6-chloro-3-pyridylmethyl) -2- (1-nitro-2-allylthioethylidene) imidazolidine (European publication No. 437784, hereinafter compound No. A-6 and Abbreviated), 1- (6-chloro-3-pyridylmethyl) -2-
(1-Nitro-2-ethylthioethylidene) imidazolidine (European publication No. 437784, abbreviated as compound No. A-7 hereinafter), 1- (6-chloro-3-pyridylmethyl) -2- (1-nitro -2-β-methylallylthioethylidene) imidazolidine (European publication N
o. 437784, the following compound No. Abbreviated as A-8),
1- (6-chloro-3-pyridylmethyl) -3-methyl-2-nitroguanidine (European publication No. 383)
091, hereinafter compound No. Abbreviated as A-9), 1- (6-
Chloro-3-pyridylmethyl) -3,3-dimethyl-2
-Nitroguanidine (European publication No. 38309
1, hereinafter compound No. A-10), 3- (6-chloro-3-pyridylmethyl) -2-nitromethylene-thiazolidine (European Publication No. 192060, hereinafter abbreviated as Compound A-11), 1- (6-chloro). -3
-Pyridylmethyl) -2- (nitromethylene) -imidazolidine (European publication No. 163855, hereinafter abbreviated as compound No. A-12), 6- (6-chloro-3-)
Pyridylmethylamino) -1,3-dimethyl-5-nitro-1,2,3,4-tetrahydropyrimidine (European publication No. 366085, hereinafter compound No. A-1
3), 1- (6-chloro-3-pyridylmethyl)
-5-nitro-3-methyl-6-methylamino-1,
Nitro compounds such as 2,3,4-tetrahydropyrimidine (European publication No. 366085, hereinafter abbreviated as compound No. A-14); dinitro compounds, organic sulfur compounds, urea compounds, triazine compounds, hydrazine compounds , And other compounds include 2-te
rt-Butylimino-3-isopropyl-5-phenyl-3,4,5,6-tetrahydro-2H-1,3,5-
Thiadiazin-4-one (generic name: buprofezin, hereinafter abbreviated as compound No. A-15), trans- (4-chlorophenyl) -N-cyclohexyl-4-methyl-2
-Oxothiazolidinone-3-carboxamide, N-methylbis (2,4-xylyliminomethyl) amine,
N '-(4-chloro-o-tolyl) -N, N-dimethylformamidine, (4-ethoxyphenyl)-[3-
(4-Fluoro-3-phenoxyphenyl) propyl]
A compound such as (dimethyl) silane (generic name: silafluofene, hereinafter abbreviated as compound No. A-16); and the like. Further, they can be mixed and used in combination with microbial agents such as BT agents and insect pathogenic virus agents, antibiotics such as avermectin and milbemycin.
Of these insecticides, acaricides and nematicides, Compound No. A-1, A-2, A-3, A-4, A-5, A-
6, A-7, A-8, A-9, A-10, A-11, A
-12, A-13, A-14, A-15 and A-16 are preferable, and Compound No. A-1, A-2, A-3, A-
6, A-15 and A-16 are more desirable.

In particular, the compound of the present invention No. 5, 34 or 35
At least one of compound No. A-1, A-2, A-
3, A-6, A-15 and at least one of A-16 are mixed, the former is 50 to 5000 g / ha, the latter is 10
When applied at a dose of up to 5,000 g / ha, it exhibits an excellent effect against harmful insects such as Trichuris chinensis, Pleurotus esculenta, planthoppers and leafhoppers.

For example, as a germicide, S-benzyl
Organic phosphorus compounds such as O, O-diisopropylphosphorothioate, O-ethyl S, S-diphenylphosphorodithioate, aluminum ethylhydrogenphosphonate; 4,5,6,7-tetrachlorophthalide;
Organochlorine compounds such as tetrachloroisophthalonitrile; Manganese ethylene bis (dithiocarbamate) polymer, zinc ethylene bis (dithiocarbamate) polymer, complex compound of zinc and manganese ethylene bis (dithiocarbamate) , Dizinc bis (dimethyldithiocarbamate) ethylene bis (dithiocarbamate), polymer of zinc propylene bis (dithiocarbamate), dithiocarbamate compounds; 3
a, 4,7,7a-tetrahydro-N- (trichloromethylsulfenyl) phthalimide, 3a, 4,7,7a
-N-halogenothioalkyl compounds such as tetrahydro-N- (1,1,2,2-tetrachloroethylsulfenyl) phthalimide and N- (trichloromethylsulfenyl) phthalimide; 3- (3,5-dichlorophenyl)- N-isopropyl-2,4-dioxoimidazolidine-1-carboxamide, (RS) -3- (3,5
-Dichlorophenyl) -5-methyl-5-vinyl-1,
3-oxazolidine-2,4-dione, N- (3,5-
Dicarboximide compounds such as dichlorophenyl) -1,2-dimethylcyclopropane-1,2-dicarboximide; methyl 1- (butylcarbamoyl) benzimidazol-2-ylcarbamate, dimethyl 4,
Benzimidazole compounds such as 4,-(o-phenylene) bis (3-thioallophanate); 1- (4-chlorophenoxy) -3,3-dimethyl-1- (1H-
1,2,4-triazol-1-yl) butanone, 1-
(Biphenyl-4-yloxy) -3,3-dimethyl-1- (1H-1,2,4-triazol-1-yl)
Butan-2-ol, 1- [N- (4-chloro-2-trifluoromethylphenyl) -2-propoxyacetimidoyl] imidazole, 1- [2- (2,4-dichlorophenyl) -4-ethyl- 1,3-dioxolane-2
-Ylmethyl] -1H-1,2,4-triazole, 1
-[2- (2,4-Dichlorophenyl) -4-propyl-1,3-dioxolan-2-ylmethyl] -1H-
Azole compounds such as 1,2,4-triazole and 1- [2- (2,4-dichlorophenyl) pentyl] -1H-1,2,4-triazole; 2,4'-dichloro-α- (pyrimidine -5-yl) benzhydryl alcohol, (±) -2,4'-difluoro-α- (1H-
Carbinol compounds such as 1,2,4-triazol-1-ylmethyl) benzhydryl alcohol; 3 '
Benzanilide compounds such as isopropoxy-o-trianilide, α, α, α-trifluoro-3′-isopropoxy-o-toluanilide; methyl N- (2-
Methoxyacetyl) -N- (2,6-xylyl) -DL
-Phenylamide compounds such as alaninate; 3-
Chloro-N- (3-chloro-2,6-dinitro-4-
Pyridinamine-based compounds such as α, α, α-trifluorotolyl) -5-trifluoromethyl-2-pyridinamine; piperazine-based compounds, morpholine-based compounds, anthraquinone-based compounds, quinoxaline-based compounds, crotonic acid-based compounds, sulfenes Acid-based compounds, urea-based compounds, and other compounds such as diisopropyl-1,3-dithiolane-2-ylidene-malonate and 5-methyl-
1,2,4-triazolo [3,4-b] benzazole, 1,2,5,6-tetrahydropyrrolo [3,2,1]
-Ij] quinolin-4-one, 6- (3,5-dichloro-4-methylphenyl) -3 (2H) -pyridazinone,
3-allyloxy-1,2-benzisothiazole-
1,1-dioxide, 1- (4-chlorobenzyl) -1
Compounds such as cyclopentyl-3-phenylurea;
And so on. Furthermore, it can be mixed and used in combination with an antibiotic such as validamycin A.

The mixing ratio of the compound of the present invention and other agricultural chemicals is
1: 100 to 100: 1, preferably 1:50 to 50:
It is 1.

Application of the pest control agent containing the compound of the present invention as an active ingredient is generally 1 to 20,000 pp.
m, preferably 1 to 2,000 ppm, and more preferably 10 to 1,000 ppm. The concentrations of these active ingredients can be appropriately changed depending on the form of the preparation, the method of application, the purpose, the time, the place, the occurrence status of the harmful insects and the like. For example, in the case of aquatic pests, it can be controlled even by spraying a drug solution having the above concentration range to the place of occurrence, so the concentration range of the active ingredient in water is the above or less. The amount applied per unit area is about 1 to 1 as the active ingredient compound per ha.
50,000 g, preferably 10 to 10,000 g, and more preferably 50 to 5,000 g are used. However, it is also possible to deviate from these ranges in special cases. In addition, the application is a method generally used in general, that is, spraying (for example, spraying, spraying, misting, atomizing, granulation, water surface application, etc.), soil application (mixing,
Irrigation, etc.), surface application (coating, dressing, coating, etc.), immersion poison bait and the like. In addition, the active ingredient is fed to livestock mixed with feed, and pests in the excrement are given,
In particular, it is possible to control the development and development of harmful insects.
In addition, the so-called ultra low volume method
ume). In this way it is possible to contain 100% of the active ingredient.

Test Example 1 Insecticide test of Spodoptera litura , each formulation of the active ingredient compound was dispersed in water to prepare 8
Leaf pieces of cabbage were immersed in a chemical solution adjusted to a concentration of 00 ppm for about 10 seconds and air-dried. Wet filter paper was spread on a Petri dish with a diameter of 9 cm, and air-dried leaf pieces were placed on it. Ten second-to-third lotus rootworm larvae were released there, covered, and allowed to stand in a 26 ° C. illuminated thermostat. Life or death was determined 5 days after the release, and the mortality rate was calculated by the following formula. Mortality rate (%) = (number of dead insects / number of released insects) × 100 Compound No. 1, 3, 5, 7-11, 13, 14,
17-20, 22-24, 27, 29, 30, 34, 3
5, 36, 37, 39 to 52 and 54 to 63 have a mortality rate of 1
00%, and No. 2 and 6 showed 90% mortality.

Test Example 2 Diamondback moth insecticidal test A test was carried out in the same manner as in the above-mentioned Test Example 1 except that the 2 to 3rd-old Monascus sp. The compound No. 1, 5, 7,
8,10,11,14,17,19,20,22,2
4,27,29,30,34,35,37,39,4
1, 43, 44, 47, 50, 57, 61, 62 and 6
3 showed a mortality of 100%.

Test Example 3 Cobnomeiga insecticidal test Each formulation of the active ingredient compound was dispersed in water to give 5
Corn leaf pieces were dipped in a chemical solution adjusted to a concentration of 0 ppm for about 10 seconds and air-dried. A wet filter paper was laid on an ice cream cup having a diameter of 8 cm, and the air-dried leaf pieces were placed on it. Five larvae of the second- and third-instar Larvae of Laminaria aequinata were released there, covered with a lid and allowed to stand in a 26 ° C. illuminated thermostat. On the 5th day after the release of insects, life or death was determined, and the mortality rate was calculated in the same manner as in Test Example 1 above.

Compound No. 5, 17, 22 and 34 showed 100% mortality.

Test Example 4 Insecticidal trial of Scutellaria japonica
Each formulation products test active ingredient compound is dispersed in water 5
Artificial feed [trade name: Insector. 6 pieces of LFR (Nippon Nosan Kogyo Co., Ltd.)
After soaking for 0 second, it was left indoors for about 1 hour. Diameter 8
A filter paper was laid on a cm ice cream cup, and the treated artificial feed was placed on the filter paper. Release 10 larvae of 2 to 3 years old Chacokakumonamaki, cover and cover at 26 ° C.
It was left in the illuminated incubator. Life or death was determined 8 to 9 days after the release, and the mortality rate was determined in the same manner as in Test Example 1 above.

Compound No. 5, 34 and 35 have a mortality rate of 1
It showed 00%.

[0069]

INDUSTRIAL APPLICABILITY According to the present invention, a novel hydrazine compound having excellent pest control activity is provided.

─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. ⁵ Identification code Internal reference number FI Technical display area A01N 57/16 101 A 7106-4H C07C 241/02 261/04 8519-4H 323/62 7419-4H 381/08 8619-4H C07D 215/48 7019-4C 277/68 7019-4C 307/84 7729-4C 333/68 7729-4C 495/04 101 7329-4C (72) Inventor Kazuhiro Yamamoto West Kusatsu City, Shiga Prefecture 2-3-1 Shibukawa Ishihara Sangyo Co., Ltd. Central Research Laboratory (72) Inventor Masayuki Morita 2-3-1, Nishi-Shibukawa Nishi Kusatsu City, Shiga Prefecture Ishihara Sangyo Co., Ltd. Central Research Center

Claims (5)

[Claims] 1. A compound represented by the general formula (I): (In the formula, A is an optionally substituted benzofuranyl group, an optionally substituted quinolinyl group, an optionally substituted benzothienyl group, an optionally substituted benzothiazolyl group, an optionally substituted thienothienyl group, and a substituted A dihydrothienothienyl group which may be substituted, a dihydrocyclopentathienyl group which may be substituted, a tetrahydrobenzothienyl group which may be substituted, an indanyl group which may be substituted or a hexahydroindanyl group which may be substituted, W Is a hydrogen atom, a cyano group, a -COCOOR 'group, -SN
(R ″) COOR ′ group or —CH ₂ OCOR ′ group, R ′ and R ″ are each independently an alkyl group or a cycloalkyl group, and R is a halogen atom or an alkyl optionally substituted with a halogen atom. A group, an alkoxy group which may be substituted with a halogen atom, an alkylthio group which may be substituted with a halogen atom or a nitro group, and n is an integer of 0 to 5, provided that when n is 2 or more, R is A hydrazine compound represented by the same kind or different kinds) or a salt thereof. 2. A compound represented by the general formula (II): (In the formula, A is an optionally substituted benzofuranyl group, an optionally substituted quinolinyl group, an optionally substituted benzothienyl group, an optionally substituted benzothiazolyl group, an optionally substituted thienothienyl group, and a substituted A dihydrothienothienyl group which may be substituted, a dihydrocyclopentathienyl group which may be substituted, a tetrahydrobenzothienyl group which may be substituted, an indanyl group which may be substituted or a hexahydroindanyl group which may be substituted) The compound represented and the general formula (III): {In the formula, R is a halogen atom, an alkyl group optionally substituted with a halogen atom, an alkoxy group optionally substituted with a halogen atom, an alkylthio group optionally substituted with a halogen atom or a nitro group, and n is 0. Is an integer from ~ 5,
However, when n is 2 or more, R may be the same or different and X is a halogen atom, an alkoxy group or -O.
A compound represented by the formula: COT group (T is an alkyl group)} is reacted with a compound represented by the general formula (I-1): (In the formula, A, R and n are as described above) A method for producing a hydrazine compound or a salt thereof. 3. A compound represented by the general formula (I-1): (In the formula, A is an optionally substituted benzofuranyl group, an optionally substituted quinolinyl group, an optionally substituted benzothienyl group, an optionally substituted benzothiazolyl group, an optionally substituted thienothienyl group, and a substituted An optionally dihydrothienothienyl group, an optionally substituted dihydrocyclopentathienyl group, an optionally substituted tetrahydrobenzothienyl group, an optionally substituted indanyl group or an optionally substituted hexahydroindanyl group, R Is a halogen atom, an alkyl group optionally substituted with a halogen atom, an alkoxy group optionally substituted with a halogen atom,
It is an alkylthio group or a nitro group which may be substituted with a halogen atom, n is an integer of 0 to 5, provided that n is 2
In the above cases, R may be the same or different.)
And a general formula W′-G (wherein W ′ is a cyano group, a —COCOOR ′ group, a —S—
N (R ") COOR a 'group or a _-CH 2 OCOR' group, R 'and R" are each independently an alkyl group or a cycloalkyl group, G is a chlorine atom or a bromine atom)
A compound represented by the general formula (I-2): (In the formula, A, W ′, R and n are as described above), and a method for producing the hydrazine compound. 4. A compound represented by the general formula (I): (In the formula, A is an optionally substituted benzofuranyl group, an optionally substituted quinolinyl group, an optionally substituted benzothienyl group, an optionally substituted benzothiazolyl group, an optionally substituted thienothienyl group, and a substituted A dihydrothienothienyl group which may be substituted, a dihydrocyclopentathienyl group which may be substituted, a tetrahydrobenzothienyl group which may be substituted, an indanyl group which may be substituted or a hexahydroindanyl group which may be substituted, W Is a hydrogen atom, a cyano group, a -COCOOR 'group, -SN
(R ″) COOR ′ group or —CH ₂ OCOR ′ group, R ′ and R ″ are each independently an alkyl group or a cycloalkyl group, and R is a halogen atom or an alkyl optionally substituted with a halogen atom. A group, an alkoxy group which may be substituted with a halogen atom, an alkylthio group which may be substituted with a halogen atom or a nitro group, and n is an integer of 0 to 5, provided that when n is 2 or more, R is A pest control agent comprising a hydrazine compound represented by the same or different kinds) or a salt thereof as an active ingredient. 5. A compound represented by the general formula (II): (In the formula, A is an optionally substituted benzofuranyl group, an optionally substituted quinolinyl group, an optionally substituted benzothienyl group, an optionally substituted benzothiazolyl group, an optionally substituted thienothienyl group, and a substituted A dihydrothienothienyl group which may be substituted, a dihydrocyclopentathienyl group which may be substituted, a tetrahydrobenzothienyl group which may be substituted, an indanyl group which may be substituted or a hexahydroindanyl group which may be substituted) The compound represented.