JPH03141245A - Hydrazine-based compound, production thereof and controlling agent against noxious animal containing the same - Google Patents

Abstract

NEW MATERIAL:A hydrazine-based compound expressed by formula I [A is either alkylene or formula IV (j and k and 1 or 2) which may be substituted with halogen or alkyl; n and m are 0 or 1; R is halogen or alkyl which may be substituted with the halogen; 1 is an integer of 0-5, provided that A is not CH2 when n and m are 1] or salt thereof. EXAMPLE:N-tert-Butyl-N-3,5-dimethylbenzoyl-N'-(2,3-dihydrobenzofuran-5 -yl- carbonyl)hydrazine. USE:A noxious animal controlling agent effective in controlling various insect pests, noxious mites and other noxious animals. PREPARATION:A compound expressed by formula II is reacted with a compound expressed by formula III (X is halogen, alkyl or alkoxy) to afford the compound expressed by formula I or salt thereof.

Description

DETAILED DESCRIPTION OF THE INVENTION (Industrial Application Field) The present invention relates to novel hydrazine compounds, methods for producing them, and pest control agents containing them.

(Prior art and background to the invention) Hydrazine compounds include, for example, JP-A-62-1
It is known from publications such as No. 67747 and JP-A No. 62-175451 that it is useful as an active ingredient of insecticides. However, although the above publication specifically discloses several points regarding the compound represented by the following -Funenin (I) in which n and m are 1 and A is -C11□- group, , compounds other than these are not specifically described with respect to the compound represented by the general formula (I). The present invention is based on the knowledge that specific hydrazine compounds exhibit high pest control effects.

(Disclosure of the Invention) The present invention relates to a hydrazine compound represented by the following shipman (I) or a salt thereof, a method for producing the same, and a pest control agent containing the same.

General formula (I) (where Δ is a halogen atom or an alkylene group which may be substituted with an alkyl group, or -(CI+□)-T-Koichi (CIlz ) r-group (j and k are each independently 1 or 2), n and m are each independently 0 or l, and R is a halogen atom or an alkyl optionally substituted with a halogen atom group, k is an integer from O to 5, provided that n and m are both 1 (not a -CII2- group).

The alkyl group contained in 8 and R in the above-Funenin (I) includes those having 1 to 6 carbon atoms, such as methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, etc. , they also include structural isomers of linear or branched fatty chains.

In addition, the alkylene group included in 8 has 1 to 6 carbon atoms.
Examples include methylene group, ethylene group, trimethylene group, tetramethylene group, pentamethylene group, and hexamethylene group. Further, the halogen atoms contained in A and R include, for example, fluorine atom, chlorine atom, bromine atom,
An example is an iodine atom. In formula (I) of -10 above, 8 represents an alkylene group which may be substituted with a halogen atom or an alkyl group, and C11□)-i-0-(CIl!) which may be substituted with a halogen atom or an alkyl group. In the alkyl group in which R is not represented and may be substituted with a halogen atom, when the number of 'l I*li is 2 or more, they may be the same or different. Also, (R)
When β of 6 is 2 or more, R may be the same or different.

Examples of the salt of the compound represented by the general formula 2N) include salts with basic substances, such as ammonium salts, alkali metal salts, and alkaline earth metal salts.

Examples of the alkali metal salts include sodium salts, potassium salts, lithium salts, etc., and examples of the alkaline earth metal salts include calcium salts, magnesium salts, barium salts, etc.

The compound represented by -Funenin (I) above can be produced, for example, by the method of the following reaction step a.

[Reaction step a]

113 113C-C-CIl:I 113 (I) (where Δ, n, m, R and l are as described above, X is a halogen atom, an alkoxy group or a -0CT group (
T is an alkyl group) Reaction step a is usually carried out in the presence of a solvent and a base.

Examples of solvents include water; aromatic hydrocarbons such as benzene and toluene; ethers such as diethyl ether and tetrahydrofuran; halogenated hydrocarbons such as methylene chloride and chloroborum; aprotic hydrocarbons such as acetonitrile and dimethylformamide. Examples of the base include solvents that are inert to the reaction, such as polar solvents, and these can be used alone or as a mixture, but a mixed solvent of water and methylene chloride or chloroform is particularly desirable.
Tertiary amines such as triethylamine; alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; alkali metal carbonates such as sodium carbonate and potassium carbonate; sodium methoxide and sodium ethoxide. Alkoxides; examples include pyridine, among which sodium hydroxide and potassium hydroxide are preferred, and the reaction temperature is usually -50°C to +100°C
and, desirably, when X in the compound represented by -Funenin (III) is a halogen atom or 1-oct, W, the temperature is 0°C to 30°C, and when X is an alkoxy group, the temperature is 50°C to 100°C. A certain 0 reaction time is usually 0.
The time is 5 to 24 hours, preferably 1 to 3 hours.

The compound represented by -Funenin (n) above can be produced, for example, by the following reaction process.

[Reaction step b]

C11゜113C-C-CIl3 1 In the formula, A, n and m are as described above, and Y is a halogen atom or an alkoxy group) The solvent used in the reaction step is the solvent used in the reaction step a. In addition to the solvents that can be used, alcohols such as methanol and ethanol can be used, and these can be used alone or as a mixture, and a mixed solvent of water and methylene chloride or toluene is particularly desirable.

Examples of the base used in the reaction step include the same bases as those used in the reaction step a, and among them, sodium hydroxide and potassium hydroxide are preferred.

The reaction temperature in the reaction step is usually -20"C to +100℃
The temperature is preferably 0°C to 50°C when Y in the compound represented by -Funenin (IV) is a halogen atom, and 80°C to 100°C when Y is an alkoxy group.

The reaction time of the reaction step is usually 0.5 to 12 hours, preferably 1 to 5 hours.

Further, the compound represented by -Funenin (IV) can be produced, for example, by the following reaction steps C to e.

[Reaction step C]

[Reaction step d] (IV-1) [Reaction step e] (V) (IV-2) In reaction step c''-e, Asn and m are as described above, Zl is a halogen atom, and 21 is It is an alkyl group.

In reaction step C, the catalyst is aluminum chloride,
Examples include Lewis acids such as ferric chloride, zinc chloride, and tin chloride; examples of solvents include halogenated hydrocarbons such as carbon tetrachloride and ethylene dichloride; carbon disulfide; and nitromethane. .

In reaction step d, examples of the solvent include water; alcohols such as methanol and ethanol; these can be used alone or as a mixture; a mixed solvent of water and methanol is particularly preferred.

In reaction step d, examples of the halogenating agent include thionyl chloride, phosphorus oxychloride, and thionyl bromide.

In the reaction step e, examples of the base include tertiary amines such as triethylamine; pyridine, etc., and examples of the solvent include solvents other than water among the solvents that can be used in the reaction step a.

Next, a specific example of synthesis of the compound of the present invention will be described.

Synthesis Example I N-t-butyl-N-3+5-dimethylbenzoyl-N'-(2,3-dihydrobenzofuran-5
Synthesis of -yl-carbonyl)hydrazine (compound 4) (I1N-To a solution of 2.3 g of t-butylhydrazine hydrochloride in methylene chloride 9011, 30n+1 of a 10% aqueous sodium hydroxide solution was added, and then 2 .3-dihydrobenzofuran-5-carbonyl chloride 3.3g
was gradually added dropwise at room temperature. After stirring at room temperature for 3 hours, water 30
11! ! The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure to extract N with a melting point of 150.4°C.
-t-butyl-N'(2,3-dihydrobenzofuran)
3.85 g of -5-yl-carbonylhydrazine was obtained.

(2) Nt-butyroux N'(2
, 3-Dihydrobenzofuran)-5-yl-carbonylhydrazine (1.5 g) dissolved in 20 mff of methylene chloride, 6 ml of a 10% aqueous sodium hydroxide solution was added, and then 1 g of 3,5-dimethylbenzoyl chloride was added.
5 ml of methylene chloride solution was gradually added dropwise at room temperature.

Stir at room temperature for 2 hours! ! After that, methylene chloride 80+
Extract by adding nff1 and water 30w + ffi,
The organic layer was washed with water and then dried over anhydrous magnesium sulfate. After distilling off the solvent under reduced pressure, the residue was washed with n-hexane,
Target compound with melting point IB3.8-186.8°C (compound Na4
) 2.0g was obtained.

Synthesis Example 2 N-t-butyl-N-(3,5-dimethylbenzoyl)-N'-(2,2,3-1-lifluorobenzodioxan-6-yl-carbonyl)hydrazine (compound number 6) Synthesis (ll dichloroethane 30Il11 ferric chloride 4
．． Add 2.2m/2.2m of acetyl chloride to the solution in which 9g of
was gradually added dropwise while maintaining the reaction solution temperature at 10°C.

Then 2.2.3-trifluorobenzodioxane 4,8
g was gradually added dropwise at the same temperature, and stirring was further continued at room temperature for 1.5 hours. Next, the reaction solution was poured into 100ml of ice water, followed by extraction with 100ml of methylene chloride, and the organic layer was washed in this order with 10% diluted hydrochloric acid, saturated aqueous sodium bicarbonate solution, and saturated brine. After drying by adding anhydrous sodium sulfate, the solvent was distilled off under reduced pressure, and the resulting residue was subjected to silica gel column chromatography (S eluent: n-
Hexane/ethyl acetate = 4.5/1) to obtain 1.9 g of 6-acetyl-2,2,3-)lifluorobenzodioxane as an oil.

(2) 6-acetyl-2,2,3 obtained in step (I) above
1.9g of trifluorobenzodioxane to 11g of methanol
5+nff1) and 5% sodium hypochlorite aqueous solution 411I11 at 18-28℃ for 30 minutes.
After gradually dropping 0 drops, the temperature was 1.5 at 45-47℃.
After stirring for an hour, cool to room temperature, wash with 10 mg of ether, add 0.31 g of sodium bisulfite to the aqueous layer, acidify with concentrated hydrochloric acid, and extract with methylene chloride. The layer was washed with saturated brine and then dried over anhydrous sulfuric acid. The solvent was distilled off under reduced pressure to obtain 1.3 g of 2.2.3-trifluorobenzodioxane-6 carboxylic acid having a melting point of 132.8°C.

(3) After reacting 0.6 g of 2,2.3-)lifluorobenzodioxane-6-carboxylic acid obtained in step (2) with 1.8 ml of thionyl chloride under reflux for 1 hour, excess chlorination Thionyl was distilled off under reduced pressure to obtain 2.2.3-trifluorobenzodioxane-6-carbonyl chloride.
．． 6 g were obtained as an oil.

Next, to a solution of 0.32 g of t-butylhydrazine hydrochloride suspended in lOmJ of methylene chloride, 4 tal of a 10% aqueous sodium hydroxide solution was added, and then the above 2.2.3-
A solution of 0.6 g of 1-lifluorobenzodioxane-6-carbonyl chloride in methylene chloride (2111) was gradually added dropwise at room temperature. After stirring at room temperature for 1.5 hours, methylene chloride 5
0II11 and water 20+j! The organic layer was washed with water and saturated brine, and then dried with anhydrous sodium sulfate. After distilling off the solvent under reduced pressure, 0.72 g of N-L-butyl-N'(2,2,3-)IJfluorobenzodioxane-6ylcarponyl)hydrazine was obtained as oil 41.

(4) N-t-butyl-N' obtained in step (3) above
0.7 g of (2,2,3-trifluorobenzodioxane-6ylcarbonyl)hydrazine was added to 1 part of methylene chloride.
3 ml of 10% aqueous sodium hydroxide solution was added to the solution dissolved in 5mff1, and then 2 ml of a methylene chloride solution containing 0.4 g of 3.5-dimethylbenzoyl chloride was gradually added dropwise at room temperature. After continuing stirring at room temperature for 1.5 hours, the reaction solution was poured into 100 ml of ice water. Extraction was performed by adding 100 mff1 of methylene chloride, and the organic layer was washed with water and saturated brine, and then dried by adding anhydrous sodium sulfate. After distilling off the solvent under reduced pressure, the residue was subjected to silica gel column chromatography (eluent: n-hexane/
Purify with ethyl acetate = 3/1) to obtain the target product (compound m6
) 0.7g was obtained. This compound was an amorphous solid and did not exhibit a clear melting point.

Next, as an intermediate for the compound of the present invention, the above-mentioned - Funato (■),
The compounds represented by (IV), (V) and (Vl) include novel compounds, and representative examples thereof are listed in Tables 1-1 to 1-4 below.

1st 1 table 1st 3 tables 1st 2 tables Table 1-4 Next, Said-Sailor (I) The compound of the present invention represented by Representative examples of these items are listed in Table 2 below.

As shown in the test examples below, the compound of the present invention exhibits activity as an active ingredient of pest control agents, particularly insecticides. For example, plant parasitic mites such as two-spotted spider mites, false red spider mites, citrus spider mites, and red mites, mealybugs, armyworms, fall armyworms, codling moths, and ballworms
*), Tobacco budworm (Lal+acco bud)
wora+), gypsy moth, Colorado potato beetle, boll weevil, cucumber beetle,
Agricultural pests such as thrips, grasshoppers, beet flies, scarab beetles, snail moths, and cabbage moths, sanitary pests such as cockroaches, houseflies, and Culex mosquitoes, and grain storage pests such as brown moths, bacterium moths, white rice beetles, and cornstarch moths. It is also effective against clothing and household pests such as burrs, burrs, termites, and flies that parasitize livestock. Furthermore, it is effective against various drug-resistant insect pests such as spider mites that are resistant to dicofol and organophosphates, and diamondback moths and houseflies that are resistant to organophosphates and pyrethroids. Furthermore, it is also effective against pneumonic gastropod molluscs such as slugs and snails. Since the compound of the present invention has systemic transferability, by treating the soil with the compound of the present invention, it is possible to control pests in the foliage and foliage at the same time as controlling soil pests.

Furthermore, the compound of the present invention has good properties as a pest control agent, such as being highly safe against beneficial ingredients including beneficial insects that do not eat useful plants, and being safe against aquatic beneficial organisms.

When using this product as an active ingredient in pest control agents, it can be used as an emulsion, powder, wettable powder, liquid, granule, paste, or small amount spraying, along with pesticide adjuvants, as in the case of conventional pesticide formulations. It can be formulated into various forms such as tablets, suspensions, and aerosols.

The mixing ratio of these ingredients is usually 0.5 to 90 parts by weight of the active ingredient and 10 to 99.5 parts by weight of the pesticide auxiliary. When these preparations are actually used, they can be used as they are, or they can be diluted to a predetermined concentration with a diluent such as water.

The agrochemical auxiliaries mentioned here include carriers, emulsifiers, suspending agents, dividing agents, spreading agents, penetrants, wetting agents, thickeners, stabilizers, etc., which may be added as appropriate. Carriers are divided into solid carriers and liquid carriers.
The body contains starch, activated carbon, soybean flour, wheat flour, wood flour, fish meal, animal and vegetable powders such as milk powder, talc, kaolin, bentonite, calcium carbonate, zeolite, siliceous earth, white carbon, clay, alumina, sulfur powder, etc. Examples include mineral powder, etc., and liquid carriers include water, alcohols such as methyl alcohol and ethylene glycol,
Ketones such as acetone and methyl ethyl ketone, ethers such as dioxane and tetrahydrofuran, aliphatic hydrocarbons such as kerosene, aromatic hydrocarbons such as xylene, -limethylbenzene, tetramethylbenzene, cyclohexane, and solvent naphtha. chloroform,
Halogenated hydrocarbons such as chlorobenzene, acid amides such as dimethylformamide, acetic acid ethyl ester,
Examples include esters such as glycerin ester of fatty acids, nitriles such as acetonitrile, and sulfur-containing compounds such as dimethyl sulfoxide.

In addition, other agricultural chemicals such as insecticides, acaricides, nematicides, fungicides, antiviral agents, attractants, herbicides,
It can be mixed or used in combination with plant growth regulators, etc., and may exhibit even better effects in this case.

For example, as an insecticide, acaricide, or nematicide,
0-(4-promo2-chlorophenyl)0-ethyl S-propyl phosphorothioate, 2,2-dichlorovinyldimethyl phosphate, ethyl 3-methyl-4-(methylthio)phenyl isopropyl phosphoroamidate, 0. 〇-dimethyl 0-4-nitro-m-
Tolyl phosphorothioate, 0-ethyl 0-4-nitrophenyl phenylphosphonothioate, 0.0-
Diethyl 0-2-isopropyl-6-methylpyrimidin-4-yl phosphorothioate, 0.0 dimethyl
0-(3,5,6-trichloro-2-pyridyl)phosphorothioate, 0. S-dimethylacetylphosphoramidothioate, 0-(2,4-dichlorophenyl)
Organic phosphate ester compounds such as 0-ethyl S-propyl phosphorodithioate; 1-naphthyl methyl carbamate, 2-isopropoxyphenyl methyl carbamate, 2-methyl-2-(methylthio)propionaldehyde O-methylcarbamoyloxime ,2
．． 3-dihydro-2,2-dimethylbenzofuran-7-
ylmethyl carbamate, dimethyl N,N'-(thiobis[(methylimino)sulfonyloxy]]bisethanimidothioate, S-methyl N-(methylcarbamoyloxy)thioacetimidate, N,N-dimethyl-2- Methylcarbamoyloxyimino-2-(methylthio)acetamide, 2-(ethylthiomethyl)phenyl methylcarbamate, 2-dimethylamino-5,6
-Simethylpyrimidin-4-yl dimethylcarbamate, S,S'-2-dimethylaminotrimethylenebis(
Carbamate compounds such as thiocarbamate), 2,
2.2-) Organochlorine compounds such as dichloro-1,1-bis(4-chlorophenyl)ethanol and 4-chlorophenyl-2,4,5-trichlorophenyl sulfone;
Organometallic compounds such as tricyclohexyltine hydroxide; (R3)-α-cyano-3-phenoxybenzyl (R3)-2-(4-chlorophenyl)-3-
Methyl butyrate, 3-phenoxybenzyl (IR3)
-cis,trans-5-(2,2-dichlorovinyl)-
2,2-dimethylcyclopropanecarboxylate (R
S)-α-cyano-3-phenoxybenzyl (IR3)
-cis,trans-5-(2,2-dichlorovinyl)-
2,2-dimethylcyclopropanecarboxylate, (
S)-α-cyano-3-phenoxybenzyl (IR)-
Cis-5-(2,2-dibromovinyl)-2,2-dimethylcyclopropanecarboxylate, (R3)-α-
Cyano-3-phenoxybenzyl (IR3)-cis, trans-3-(2-chloro-3,3,3-)lifluoropropenyl)-2,2-dimethylcyclopropanecarboxylate, 4-methyl-2,3 , 5,6-titrafluorobenzyl-3-(2-chloro-3,3,3-)lifluoro-1-propen-1-yl)-2,2-dimethylcyclopropane carboxylate, etc.
system compound; I-(4-chlorophenyl):3-(2
, (i-difluorobenzoyl)urea, 1-(3,5
-dichloro-4-(5-chloro-5-trifluoromedy-2-pyridyloxy)pheny/I')-3-(2,
6-difluorobenzoyl)urea, 1-(3,5-dichloro-2,4-difluorophenyl)-3-(2,6
-benzoylurea-based compounds such as (difluorobenzoyl)urea; Lance-(4-Rophenyl)-N-cyclohexyl-
4-Methyl-2-oxothiazolidinone-3-carboxamide, N-methylbis(2,4-xylyliminomethyl)amine, N'-(4-chloroa-o-tolyl)N,N
- Compounds such as dimethylformamidine; isopropyl-(2E,4E)-11methoxy3.7.11- t-
Juvenile hormone-like compounds such as dimethyl-2,4-dodecagenoate; and other compounds include dinitro compounds, organic sulfur compounds, urea compounds, l-riazine compounds, and pyridazinone compounds.

Furthermore, it can also be used in combination with microbial pesticides such as BT agents and insect pathogenic virus agents.

For example, the fungicides include S-benzyl, 0゜0-diisopropyl phosphorothioate, O-ethyl S, S
-Organophosphorus compounds such as diphenyl phosphorodithioate and aluminum conityl-1-; 4.5.6.7-
Organochlorine compounds such as titrachlorophthalide and tetrachloroisophthalonitrile; polymers of Manganese ethylene bis (dithiocarbamate), polymers of zinc ethylene bis (dithiocarbamate), zinc and Manganese ethylene bis (dithiocarbamate) dithiocarbamate compounds such as complex compounds with zinc bis(dimethyldithiocarbamate)-ethylene bis(dithiocarbamate), and polymers of zinc propylene bis(dithiocarbamate); 3a,4,7,7a-tetrahydro-N(trichloro methylsulfenyl)phthalimide,
N-halogenothioalkyl compounds such as 3a, 4, 7.7a -tetrahydronote] - 1-edylsulfenyl) phthalimide, N-(trichloro[1-methylsulfenyl) phthalimide 3-(3 .5-dichlorophenyl)-N-isobutyl: Ibiru-2.4-dioxoimidazolidine-1-carboquinamide, (R S)-
3-(3.5-dichlorophenyl)-5-methyl-5-
Vinyl-1,3-oxazolidine-2,4-dione, N
Dicarboximide compounds such as -(3.5-dichlorophenyl)-1,2-dimethylcyclopropane-1,2-dicarboximide; methyl 1-(butylcarbamoyl)penzimidadz-2-yl carbamate, dimethyl 4 .Benzimidazole compounds such as 4'-(o-phenylene)bis(3-thioallophanate); 1
-(4-chlorophenoxy)3,3-dimethyl-1 -
(1 11-1.2.4-triazol-1-yl)butanone, ■-(biphenyl4-yloxy) -3
．． 3-dimethyl-1-(I+1 1.2./l-)riazol-1-yl)butan-2-ol, l- (N-
(4-chloro-2-trifluoromethylphenyl)-
・2-propoxyacetimidoylcoimidazole, 1
-(2-(2.4dichlorophenyl)-4-ethyl-1
．． 3-dioxolan-2-ylmethyl) I H-1
．． 2.4-1-riazole, 1-(2-(2.
4-dichlorophenyl)4-propyl-1,3-dioxolan-2-ylmethyl)-1 11-1.2.
(±)-2.4'
-dichloro-α-(pyrimidin-5-yl)benzhydryl alcohol, 2.

4′-difluoro-α-( 1 [1-1.2.4 −
Carbinol compounds such as triazol-l-ylmethyl)benzhydryl alcohol; 3'-isopropoxy-o-)luanilide, α, α. Benzanilide compounds such as α-trifluoro-3'-isopropoxy-0-)lylanilide; Acylalanine compounds such as methyl N(2-methoxyacetyl)-N-(2,6-xylyl)-DL-alaninate; 3-chloro- N-(
3-chloro-2,6-dini-l-rho-4-α,α,α-trifluorotolyl)-5-1-lifluoromethyl-2
- Pyridinamine compounds such as viridinamine; other compounds include piperazine compounds, morpholine compounds, anthraquinone compounds, quinoxaline compounds, crotonic acid compounds, sulfenic acid compounds, urea compounds, antibiotics, etc. It will be done.

The pest control agent of the present invention is effective for controlling various pests, harmful mites, and other harmful animals, and is generally applied in one step.
~20.000ppm, preferably 20-2.000
Perform at an active ingredient concentration of ppa+. The concentration of these active ingredients can be changed appropriately depending on the form of the preparation, application method, purpose, timing, location, pest outbreak situation, etc. For example, in the case of aquatic pests, a chemical solution with the above concentration range can be sprayed on the outbreak site. The concentration range of the active ingredient in water is below the above range because it can be controlled even if it is treated with water.

The application per unit area is about 0.1 to 5,000 g, preferably 5 to 1 g of active ingredient compound per 10a.
,000 g is used. However, deviations from these ranges are possible in special cases.

Application of the various formulations containing the compounds of the present invention, or dilutions thereof, can be carried out using commonly used application methods, i.e. Ilk cloth (e.g. spreading, spraying, misting, atomizing, water surface application, etc.) - 1 soil Application (mixing, irrigation, etc.),
It can be carried out by surface application (painting, powder coating, coating, etc.), immersion of poison bait, etc.

In addition, the so-called ultra-high concentration low
It can also be applied depending on the volume. In this way, 100% active ingredient content is possible.

Disperse each formulation of the active ingredient compound in water-U,
Cabbage leaf pieces were immersed in a chemical solution adjusted to a concentration of 800 ppm for about 10 seconds and air-dried. A moist filter paper was placed in a 9 cm diameter veterinary dish, and the air-dried leaf pieces were placed on top of the moist filter paper.

Ten 2nd to 3rd instar Spodoptera larvae were released there, the lid was placed, and the larva was left in a lighted incubator at 26°C. After release 5
The mortar was determined to be alive or dead, and the mortality rate was calculated using the following formula.

All of the compound fish 2 to 12 showed a mortality rate of 100%.

Amount 211 Koga 8 Amount □゛A test was conducted in the same manner as in Test Example 1 above to determine the mortality rate, except that 2nd to 3rd instar Spodoptera were replaced with 2nd to 3rd instar diamondback moth.

The compounds N112 and 4-12 showed a mortality rate of 100%.

3 Disperse each formulation of the Hasmonyo active ingredient compound in water,
A drug solution of 00 ppm+ was prepared.

Cabbages planted in vinyl pots (diameter 8 cm, height 7 cm) were treated by irrigation with the above chemical solution 101n1.

Seven days after the treatment, one or two leaves were cut and placed in a Petri dish with a diameter of 9 cm lined with moist filter paper, into which 10 2nd or 3rd instar Spodoptera larvae were released, covered with a lid, and exposed to light at 26°C. It was left in a thermostat. Determine whether the animal is alive or dead at the 5th mound after release.
Mortality rate was determined in the same manner as in Test Example 1.

The compound positive 4 showed a mortality rate of 100%.

Next, formulation examples of the present invention will be described, but the compounds, compounding ratios, dosage forms, etc. of the present invention are not limited to the described examples.

Formulation Example 1 (a) Compound A2 20 parts by weight (b) Kaolin 72 parts by weight (c) Sodium ligninsulfonate 8 parts by weight or more are uniformly mixed to prepare a wettable powder.

Formulation Example 2 (a) 5 parts by weight of Compound 12 (b) 95 parts by weight or more of talc are uniformly mixed to form a powder.

Formulation Example 3 (a) Compound 6 20 parts by weight (b) N,
20 parts by weight of N'-dimethylformamide (c) Polyoxyethylene alkylphenyl ether
10 parts by weight (d)xylene
Mix and dissolve 50 parts or more of the ingredients uniformly to make an emulsion.

Formulation Example 4 (a) Kaolin 68 parts by weight (b) Sodium lignin sulfonate 2 parts by weight (c) Polyoxyethylene alkylaryl sulfate - 1-5 parts by weight (d) Silica 25 parts by weight or more The mixture of components and compound 111f18 are mixed in a weight ratio of 4=1 to form a wettable powder.

Formulation Example 5 (a) Compound Fish 10 40 parts by weight (b) Oxylate fluoride polyalkylphenol phosphate triethanolamine 2 parts by weight (c) Silicone 0.2 part by weight (d)
Xanthan gum 011 parts by weight (e) Ethylene glycol 5 parts by weight (f) water
52.7 parts by weight or more are uniformly mixed and pulverized to make a flowable agent.

Formulation Example 6 (a) Compound 11h5 50 parts by weight (b) Oxylated polyalkylphenyl phosphate-triethanolamine 2 parts by weight (c) Silicone 0.2 parts by weight (d)
Add 47.8 parts by weight or more of water to the pulverized stock solution and add (B) 5 parts by weight of sodium polycarboxylate (F) Anhydrous sodium sulfate
Add 42.8 parts by weight, mix uniformly, and dry to obtain a dry flowable agent.

Formulation Example 7 (a) Compound 4 5 parts by weight (b) Polyoxyethylene octylphenyl ether
1 part by weight (c) 0.5 part by weight of polyoxyethylene phosphoric acid ester (d) 93.5 parts by weight of granular calcium carbonate (a) to (c) were mixed uniformly in advance and diluted with an appropriate amount of acetone. After that, (d) was sprayed to remove the acetone and prepare granules.

Formulation Example 8 (a) Compound 7 2.5 parts by weight (b) N
- Methyl-2-pyrrolidone 2.5 parts by weight (c) Soybean oil 95.0 parts by weight or more are uniformly mixed and dissolved to form a micro-spraying agent (ultra
(low volume formulation)
shall be.

Formulation Example 9 (a) Compound 9 5 parts by weight (b) N,
15 parts by weight of N'-dimethylformamide (iii) polyoxyethylene alkylaryl (anyl
) Ether 10 parts by weight (d)xylene
70 parts by weight or more are mixed uniformly to form an emulsion.

Claims (1)

[Claims] 1. General formula (I) ▲There are numerical formulas, chemical formulas, tables, etc.▼... (I) {In the formula, A is a halogen atom or an alkylene group which may be substituted with an alkyl group, or may be substituted with a halogen atom or an alkyl group ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ group (j and k are each independently 1 or 2), and n and m are each independently 0 or 1, R is a halogen atom or an alkyl group optionally substituted with a halogen atom, l is an integer of 0 to 5, provided that when n and m are 1 at the same time, A is not a -CH_2- group } or their salts. 2. General formula (II) ▲There are mathematical formulas, chemical formulas, tables, etc.▼...(II) (In the formula, A is a halogen atom or an alkylene group that may be substituted with an alkyl group, or a halogen atom or an alkyl group. ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ groups (j and k are each independently 1 or 2), and n and m are each independently 0 or 1, provided that , n and m are 1 at the same time, A is not a -CH_2- group) and general formula (III) ▲There are mathematical formulas, chemical formulas, tables, etc.▼...(III) (In the formula, R is halogen an alkyl group that may be substituted with an atom or a halogen atom, l is an integer of 0 to 5,
(X is a halogen atom, an alkyl group, or an alkoxy group) General formula (I) ▲There are mathematical formulas, chemical formulas, tables, etc.▼...(I) (In the formula , A, n, m, R and l are as described above) or a salt thereof. 3. General formula (I) ▲There are mathematical formulas, chemical formulas, tables, etc.▼... (I) {In the formula, A is an alkylene group that may be substituted with a halogen atom or an alkyl group, or a halogen atom or an alkyl group ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ groups (j and k are each independently 1 or 2), n and m are each independently 0 or 1, and R is a halogen atom or an alkyl group which may be substituted with a halogen atom, l is an integer of 0 to 5, provided that when n and m are both 1, A is not a -CH_2- group}. A pest control agent characterized by containing a compound or a salt thereof as an active ingredient.