JPH0692935A - N-substituted indole derivative, its productin and insecticidal composition with the same as active ingredient - Google Patents

Abstract

PURPOSE:To provide a new compound having excellent insecticidal activity, useful as a controlling agent for noxious organisms in paddy fields, agricultural fields, orchards, forests, or environmental and hygienic circumstances, or as a parasite controlling agent for humans or animals. CONSTITUTION:The compound of formula I (X is CH, N or C-halogen; Y is H, alkyl, alkenyl, alkynyl, alkoxy, halogen, CN, OH2, etc.; R<1> is alkyl, haloalkyl, alkoxy, or haloalkoxy; R<2>-R<4> are each H, alkyl, alkenyl, alkynyl, halogen, CN, formyl, carboxyl, alkoxycarbonyl, alkylcarbonyl, NO2, cyanato, etc.; m is 0-2; n is 0-4), e.g. 1-(3-chloro-5-trifluoromethylpyridine-2-yl)-3)(dichlorofluoromethylthio) indole. The compound of the formula I can be obtained by reaction of a compound of formula II with a sulfinyl halide of formula R<1> S-halogen to produce a compound of formula III, which is then made to react with a compound of formula IV (Z is halogen).

Description

Description: FIELD OF THE INVENTION The present invention belongs to indoles.
Novel compounds, intermediates for producing these compounds, and
To the methods for producing these compounds and their intermediates.
And the derivatives are paddy fields, upland fields, orchards, forests.
Or use as an insecticide in environmental hygiene situations
You can In addition, the derivative may cause human or animal damage to parasites.
Can be used as a parasite control agent to protect against
it can. N-substituted indoles having agrochemical activity
No. 3290332 and Japanese Patent Application Laid-Open No. 55-
No. 151505, but in this case
Aryl and pyridyl groups are not included as substituents on elementary atoms.
It is not rare and its use is as a fungicide rather than an insecticide.
It Problems to be Solved by the Invention Paddy fields, uplands, orchards,
Pest control scenes in forest or environmental hygiene situations
It has higher insecticidal activity and harms beneficial insects and the environment.
There is a need for compounds that have the property of not spilling and that have low toxicity.
There is. Recently, known insecticides such as organophosphorus agents
Shows resistance to carbamate agents, pyrethroids, etc.
The number of pests has increased and it has become difficult to control them.
Ip drug is required. The present invention is a beneficial insect, ring
It does not substantially harm the environment, has low toxicity and is drug resistant.
A new type of insecticidal compound that is also effective against insects, those
And an intermediate compound for producing
The present invention is intended to provide an insecticidal composition. To achieve the above object
As a result of earnest research into the general formula (1): [In the formula, X represents a CH, N, or C-halogen atom;
Y is hydrogen, C ₁ -C _Five Alkyl, C ₂ -C _Five Alkenyl
Base, C ₂ -C _Five Alkynyl group, alkoxy group, halogen
N, cyano, nitro, C ₁ -C _Five Haloalkyl, C ₁ −
C _Five Haloalkoxy, C ₂ -C _Five Haloalkenyl or
C ₂ -C _Five Represents haloalkenyl; R ¹ Is an alkyl,
Represents haloalkyl, alkoxy or haloalkoxy
Do; R ² , R ³ , And R ^Four Are each independently hydrogen,
C ₁ -C _Five Alkyl, C ₂ -C _Five Alkenyl group, C ₂ −
C _Five Alkynyl group, halogen, cyano, formyl, cal
Voxyl, alkoxycarbonyl, haloalkoxycarl
Bonyl, alkylcarbonyl, haloalkylcarboni
Le, nitro, cyanato, thiocyanato, C ₁ -C _Five Halo
Alkyl, C ₁ -C _Five Alkoxy, C ₁ -C _Five Halo al
Coxy, C ₂ -C _Five Haloalkenyl or -S (O) k
R ^Five (Where k is 0, 1 or 2, and R ^Five Is not placed
Replacement C ₁ -C _Five Alkyl or the same or different 1
C substituted with one or more halogen atoms ₁ -C _Five Al
Kill is shown); m is 0, 1 or 2; n is
0, 1, 2, 3 or 4]
The indole derivative has excellent insecticidal activity.
Found and completed this research. The compound of the general formula (1) of the present invention is
Can be manufactured by the method. Method 1 General formula (3) [R in the formula ¹ -R ³ , M and n have the same meaning as above.
It ] And an indole derivative represented by the general formula (5): [In the formula, Z represents halogen, X, Y and R ¹ Is the text
Medium has the same meaning as above. ] In the presence of a base
By reacting with the general formula (2): [In the formula, X, Y, R ² -R ^Four And n are the same as above in the text
Has meaning. ] Intermediate and then halogenated
Sulfinyl R ¹ S-halogen atom (in the formula, R ¹ Is al
(Kill or haloalkyl) and required in organic solvent
Reaction in the presence of a base such as a tertiary amine
Is prepared by. Method 2 General formula (4): [R in the formula ² , R ³ And n have the same meaning as above in the text
It ] Indole derivative represented by
Finil R ¹ S-halogen atom (in the formula, R ¹ Is alkyl
Or haloalkyl) and if necessary in an organic solvent.
By reacting in the presence of a base such as a tertiary amine.
The intermediate represented by the general formula (3) is prepared, and then
Preparation by reacting the compound of general formula (5) in the presence of a base.
Made. The reaction is carried out by reacting the compound of the general formula (4) with the general formula
The compound of (5) or the compound of general formula (3) and the general formula
The compound (5) can be used in any ratio.
However, they are preferably used in an equimolar ratio or almost an equimolar ratio. salt
Examples of the group include sodium hydride and potassium hydroxide.
Inorganic bases such as sodium hydroxide, triethylamine
Organic bases such as pyridine and pyridine can be used. Organic salts such as triethylamine and pyridine
If a group is used, use it in a large excess and use it as a solvent.
I can do it. The amount of base should be theoretical or in excess.
However, the theoretical amount is preferably 1.0 to
Use a 5.0-fold excess. The solvent is an inert solvent for the reaction product.
For example, aliphatic hydrocarbons such as hexane and heptane,
Aromatic hydrocarbons such as benzene, toluene, xylene,
Such as chloroform, dichloromethane, chlorobenzene
Halogenated hydrocarbons, diethyl ether, tetrahydr
Ethers such as Rofuran, N, N-dimethylformua
Amides such as amides, acetonitrile, propionitri
And nitriles such as ruble. A mixture of these
It is also possible to use a medium and a mixed solvent of these and water. The reaction is carried out at a temperature from -20 ° C to the boiling point of the solvent.
Temperature range, but preferably 0 ° C to 80 ° C
Is the range. General formulas (1), (2) and (3)
The reaction mixture during the production of the compound was stirred for a sufficient time.
Usual post-treatment such as extraction, washing with water, drying, evaporation of solvent, etc.
The object is recovered by the process. Do a simple solvent wash
In many cases, it is sufficient, but if necessary, recrystallization or
Can be purified by column chromatography.
Wear. The compound of the general formula (1) of the present invention is used.
In this case, depending on the purpose of use, it may be used as it is or the effect may be promoted.
Agricultural chemicals are added to stabilize
According to the method generally used in the manufacturing field, powder
Agent, fine granule, granule, wettable powder, flowable agent, emulsion, my
Black capsule, oil, aerosol, fumigant (mosquito repellent)
Incense sticks, electric mosquito coils, etc.)
Prepare a composition in any formulation such as fumigant, poison bait, etc.
Can be used. These various formulations are suitable for practical use.
Can be used directly as is, or with water to the desired concentration.
It can be diluted and used. Agricultural aids mentioned here
Carriers (diluents) and other auxiliaries such as
It includes adhesives, emulsifiers, wetting agents, dispersants, fixing agents, disintegrating agents, etc.
You can get it. Liquid carriers include toluene and xylene.
Aromatic hydrocarbons such as len, butanol, octano
Alcohols such as alcohol and glycol, keto such as acetone
Amines, such as dimethylformamide, dimethyls
Sulfoxides such as rufoxide, methylnaphthalene, and
Clohexanone, animal and vegetable oils, fatty acids, fatty acid esters
Examples include petroleum fractions such as throat or kerosene and light oil, and water.
It Solid carriers such as clay, kaolin and tar
Ku, diatomaceous earth, silica, calcium carbonate, montmorillonite
, Bentonite, feldspar, quartz, alumina, sawdust, etc.
can give. The emulsifier or dispersant is usually an interface
Activators are used, eg higher alcohol sodium sulfate
Um, stearyl trimethyl ammonium chloride,
Polyoxyethylene alkyl phenyl ether, lauri
Anionic surfactants such as rubetaine, cationic boundaries
Surfactants, nonionic surfactants, zwitterionic surfactants
There are sex agents. Also, as a spreading agent, polyoxyethylene
Rennonyl phenyl ether, polyoxyethylene laur
Examples include ril ether, and as a wetting agent
Ciethylene nonyl phenyl ether dialkyl sulfosa
Cucinate is used as a sticking agent
Chill cellulose, polyvinyl alcohol, etc.
As disintegrants, sodium lignin sulfonate, LA
Examples include sodium uryl sulfate. Further, these compounds of the present invention are two or more compounds.
It is also possible to develop a better insecticidal effect by combined use.
It is possible and also possible to use other bioactive substances such as
, Phthalthrin, Permethrin, Decamethrin, Hue
Pyrethroids such as valbarate and cycloprothrin
And various isomers, pyrethrum extract, DDVP, phenyl
Organophosphorus insecticides such as thione, diazinon and temefos
Agents, NAC, MTMC, BPMC, pyrimers, etc.
Bamate insecticide, other insecticide, acaricide or
Fungicides, nematicides, herbicides, plant growth regulators, fertilizers, B
Mixing with T agent, insect hormone agent and other agricultural chemicals
To produce a more versatile composition with superior potency
It can also be expected, and it can be expected to have an additional effect. Further, for example, piperonyl butoxy
Pyrethroids such as dox, sulphoxide, and safloxane
By adding what are known as synergists for
This potency can be multiplied. In addition, the compound of the present invention
The product is highly stable to light, heat, oxidation, etc., but is oxidized if necessary.
Inhibitors or UV absorbers such as BHT, BH
Phenols such as A and α-naphthylamine
Use reel amines or benzophenone compounds
The effect will be more stable if added as a fixed agent.
Different compositions can be obtained. In the composition of the present invention
The active ingredient content is the formulation form, application method and other conditions
Depending on the case, only the active ingredient compound may be required
Is usually 0.2 to 95% (weight), preferably 0.5 to 8
It is in the range of 0% (weight). The amount of the composition of the present invention used depends on the dosage form and application.
Agricultural and horticultural use, depending on method, time, and other conditions
Agents, agents for forest pests, and agents for pests of Makino are usually 10 A
The amount of active ingredient per unit is 10 to 300 g, preferably 15 to 2
00g is used, and the sanitary and insect repellent agent is usually 1m ² Winning
The amount of the active ingredient used is 2 to 200 mg, preferably 5 to 100 mg.
Used. For example, powder is an active ingredient per 10 are
15-120g, granules 30-240g as the active ingredient,
Emulsions and wettable powders are active ingredients in the range of 40 to 250 g.
It However, in special cases, beyond these ranges
Can be lower or lower, and sometimes
Is even necessary. Further, in order to control parasites, one of the present inventions is used.
When the compound of general formula (1) is used,
Can be used in doses equivalent to 1 to 200 mg / kg
It The exact dose for a given condition can be
Various factors that can be determined, such as
Substance, type of parasite, formulation used and parasite
It depends on the human or animal condition. Specific examples to which the insecticidal composition of the present invention can be applied
Name the pests. From the order Hemiptera [Hemiptera]
For example, Nepho-tettix
cincticeps), sedge loacher (Sogate)
llafurcifera), brown planthopper (Nil
aparvata longe-ns), Himetobibunka
(Laodelfax stratellus),
Rabbit bug (Riptortus clavat)
us), Southern green stink bug (Nezaravirid)
ula), Nasigumbai (Stephanit-is)
nasi), Whitefly Whitefly (Trialeuro)
des vapororium), cotton aphid
(Aphis gossypii), Momoi Abram
Shi (Myzus persicae), Yanokanekaiga
Aphid (Unasqy y-anonensis),
From the order of Lepidopters, for example
Phosphoro-ringo
neella), diamondback moth (Plutella xylo)
stella), Watamiga (Promalac-tis)
inonisema) Red-tailed squirrel (Adoxophyes oran)
a), Leguminivora g
lycinivorella), Cobnomeiga (Cna)
phalocrocus medicalis), Nika
Maiga (Chill-o superlessali
s), Awanomeiga (Ostrinia fu-rna)
calis), armyworm (Mamestra bras)
sicae), armyworm (Pseudaletia)
separa, and Spodoptera
litura), rice beetle (P-arnara g)
Uttata, Pieris rapae (Pieris ra)
Paecrucivora), Heliotis (Helio)
this spp. ), Yaga (Agrotis sp.
p. ), From the order Coleoptera, for example
Douganebuibu (Anomala cuprea),
Japanese beetle (Popil-lia japonic)
a), Weevil (Echinocnemus s-)
oqameus), rice weevil (Lissorh)
optrus ory-zophilus, Oulema ory
zae), the horned beetle, Anthrenu
s verbasic), Coconut (Tenebro)
des mauritanicus), weevil
(Sitophilus zeamis), Nijuya
Henosepilacna vi-
gintioctopuncata), Azukizoum
Shi (Callosob-ruchus chinens
is), pine woodpecker (Monoch-amu)
s alternatus, sorghum beetle (Aulacophora f.
emoralis), Leptino Tulsa desemlineata
(Leptation tarsa decline line
a), Fedon Cochleariae (Phaedon c)
ochlearias), diaprotica (Diabro)
tica spp. ), Hymenopteran [Hymenopter
a], for example, a beetle (Athalia)
Rosae japonensis), Rurichu range
Hager (Argesimilis) Diptera [Dipte
Ra] is, for example, Culex
pipiens fatigans), Aedes aegypti
(Aedes aegypti), Soybean gall midge
(Asphondylls sp.), Melanogaster (Hy
lemyaplatura), Musca domestic (Musca domestic)
a viclna), fruit fly (Dacus cuc)
urcitae), rice leafhopper (Agromyz)
aoryzae), fruit fly (Lucllia sp.
p. ) Human as an Aphan-iptera
Chisel (Pulex irritans), Keob Snez
Minomi (Xenopsylla cheopis)
Nunomii (Cteno-cephalides cani)
s), as a Thysanoptera. [0030] Thrips palmi (Scirtoto)
rips dorsalls), Negiya thrips (T
grips tabaci), Southern yellow thistle
Thrips palmi, Rice thrips (B
aliotrips b-iformis), lice
As an eye [Anoplura], for example, white lice
(Pediculs humanus corpori
s), lice (P-thirus pubis), and Pseudococcidae [Psocoptera]
As an example, for example, T-logium pu
lsatorium), Hiratachate (Liposc)
e-lis bostrichophilus), straight wing
As an eye [Orthotera]
talpa africana), locust locust (Lo)
(custa migratoria), Kobaneago
(Oxya ye-zoensis), German cockroach
Li (Blattella german-ca) black
Cockroach (Periplaneta fuligino)
sa). In addition, the insecticidal composition of the present invention can be used.
Following are the most important parasites and
However, it is not limited to these. The disease product Bilharziosis or Schistosoma mansoni Schistosomiasis S. Japanicum S. Haematobium (schistosomiasis, fluke) Ancyclostomiasis Necator americanus, Ancyclostoma duode- nale (hookworm, nematode) Ascariasis Ascaris lumbricold- es (roundworm, C. elegans) [0034] Filariasis or Wuchereria bancrof- elephantiasis ti Brugia malayi (nematode) Onchoceriasis or Onchocerrca volvul-river blindues us (nematode) Loisis Loa loa (eyeworm, nematode) [Examples] The present invention will be described below with reference to Examples.
The present invention is not limited to these. Synthesis Example 1 1- (3-chloro-5-trifluoromethylpyridine-
2-yl) Synthesis of indole; 2.00 g of indole
Dissolve in 20 ml of dimethylformamide, ice-cool, nitrogen gas
Add 0.69 g of sodium hydride (60%) under flow,
After stirring for 30 minutes, dissolve in 4 ml of dimethylformamide.
Solved 2,3-dichloro-5- (trifluoromethyl)
3.70 g of pyridine was added dropwise under ice cooling. 6 after dropping
Heat to 0 ° C. and stir at that temperature for 2.5 hours. After returning to room temperature, it is poured into water and ethyl acetate is added.
Extracted. The resulting ethyl acetate layer was washed with water and anhydrous sulfuric acid
Dry over magnesium and concentrate under reduced pressure. Residue
Column chromatography (silica gel, eluent: n-
Purify with hexane / ethyl acetate = 30/1) to obtain the desired 1
-(3-chloro-5-trifluoromethylpyridine-2
4.85 g (yield: 95%) of indole was obtained.
mp 52-53 ° C. Synthesis Example 2 1- (3-chloro-5-trifluoromethylpyridine-
2-yl) -3- (dichlorofluoromethylthio) yne
Synthesis of dol; 1- (3-chloro-5-trifluorome
Chlorpyridin-2-yl) indole 1.00 g chloride
Dissolve in 10 ml of methylene, add 0.26 ml of pyridine
It Dichlorofluoromethane sulfone was added to the solution under ice cooling.
1.20 g of phenyl chloride was added dropwise, and the mixture was stirred at room temperature for 4 hours.
I stirred. The solvent was distilled off under reduced pressure and the residue was columned.
Chromatography (silica gel, eluent n-hexane)
Purified with 1- (3-chloro-5-trifluoro)
Methylpyridin-2-yl) -3- (dichlorofluoro)
1.38 g (yield 95%) of methylthio) indole was obtained.
It was mp 101-104 ° C. Synthesis Example 3 3- (dichlorofluoromethylthio) -5-fluoroi
Synthesis of ndol; 1.00 g of 5-fluoroindole
Dissolve in 10 ml of methylene chloride and 0.7 ml of pyridine
After addition, the solution was dissolved in 10 ml of methylene chloride under ice cooling.
Chlorofluoromethanesulfenyl chloride 1.5g
Was dropped and reacted at room temperature for 2 hours. 100 ml of ethyl acetate
And 100 ml of n-hexane were added, and the organic layer was added with 10% hydrochloric acid.
It was washed twice with an aqueous solution and once with water. The obtained organic layer was dried over anhydrous magnesium sulfate.
After drying, the solvent was distilled off under reduced pressure to obtain the desired 3- (dichloro)
Fluoromethylthio) -5-fluoroindole was 1.
8 g (yield 91%) was obtained. Synthesis Example 4 1- (3-chloro-5-trifluoromethylpyridine-
2-yl) -3- (dichlorofluoromethylthio) -5
-Synthesis of fluoroindole; 3- (dichlorofluoro
Dimethyl methylthio) -5-fluoroindole (0.6 g)
Dissolved in 15 ml of chillformamide, cooled with ice, under a nitrogen stream
Sodium hydride (60%) 0.1 g was added at 30 minutes
After stirring, it was dissolved in 2 ml of dimethylformamide.
2,3-dichloro-5- (trifluoromethyl) pyridy
0.5 g of water was added dropwise under ice cooling. After the dropping is finished, the temperature is raised to 100 ° C.
And stirred for 3 hours. After returning to room temperature, pour into water and add acetic acid.
Mixed solvent of 100 ml of chill and 100 ml of n-hexane
It was extracted with. The obtained organic layer is washed with 10% hydrochloric acid and water
Dried over anhydrous magnesium sulfate and concentrated under reduced pressure.
It was Column chromatography of the residue (silica gel,
Purified with eluent n-hexane / ethyl acetate = 30/1)
Target 1- (3-chloro-5-trifluoromethylpi
Lydin-2-yl) -3- (dichlorofluoromethylthio)
E) 0.6 g of 5-fluoroindole (yield 60
%)Obtained. mp107-108 ° C. Next, represented by the general formula (1) according to the present invention.
Table 1 shows typical examples of such compounds. [Image Omitted] [Table 1] Table 1-A No. XY m R ¹ R ² R ³ R ^Four 1 N CF ₃ 0 CCl ₂ F H H Cl 2 C-Cl CF ₃ 0 CCl ₂ F H 5-Cl Cl 3 N CF ₃ 0 CCl ₂ F H 5-CN Cl 4 N CF ₃ 0 CCl ₂ F H 5-F Cl 5 N CF ₃ 0 CCl ₂ F H 5-OMe Cl 6 N CF ₃ 0 CCl ₂ F Me H Cl 7 C-Cl CF ₃ 0 CCl ₂ F H H Cl 8 C-Cl Cl 0 CCl ₂ F H H Cl 9 C-Cl CF ₃ 1 CCl ₃ H H Cl 10 C-Cl CF ₃ 2 CCl ₃ H H Cl 11 N CF ₃ 0 CCl ₂ F H 6-Cl C1 12 N CF ₃ 0 CCl ₂ F H 4-Cl C1 13 C-Cl CF ₃ 0 CCl ₃ H H C1 Next, it is represented by the general formula (2) according to the present invention.
Table 2 shows typical examples of the compounds. [Image Omitted] Table 2 Table 2 No. XY R ₂ R ₃ R _Four mp (° C) (refractive index nD25) 14 C-Cl CF ₃ H H Cl (1.5851) 15 N CF ₃ H H Cl 52-53 16 C-Cl CF ₃ H5-ClCl96-9717NCF ₃ H5-MeOCl (1.5763) 18NCF ₃ Me H Cl 115-118 Next, it is represented by the general formula (3) according to the present invention.
Table 3 shows typical examples of such compounds. [Image Omitted] [Table 3] Table 3 No. m R ¹ R ² R ³ mp (° C) 190 CCl ₂ F H 5-F 200 CCl ₂ F H 5-CN Next, the insecticidal composition will be specifically described using formulation examples.
explain. Formulation Example 1. 20 parts of the compound of emulsion compound No. 1 with xylene-methylnaphtha
Add 65 parts of a mixed solution of ren to dissolve, then add to this
Luphenol oxide ethylene condensate and alkylbenzenes
Mix 15 parts of calcium ruphonate mixture (8: 2)
As an emulsion. This product should be diluted with water and used as a spray solution.
It Formulation Example 2. Wettable powder Compound No. 1 (20 parts), kaolin (35 parts), clay
30 parts of diatomaceous earth and 7.5 parts of lauric acid
Mixture of sodium dinaphthyl methanesulfonate
7.5 parts of (1: 1) were mixed and pulverized to obtain a dust.
This product is diluted with water and used as a spray solution. Formulation Example 3. Dust compound 1 part of compound No. 8 with talc and calcium carbonate
Add 97 parts of the mixture (1: 1), mix and grind thoroughly
After dispersing and blending, 2 parts of silicic acid anhydride was added, and mixed powder
Crushed into powder. Disperse this product as it is before use. Formulation Example 4. Granules Compound No. 8 compound 2 parts bentonite fine powder 48
Part, talc 48 parts, sodium lignin sulfonate 2 parts
After mixing with, add water and knead until uniform. next
Granulate through an injection molding machine and pass through a granulator and a dryer screen.
To give a granule having a particle size of 0.6 to 1 mm. This product is directly
It is used by dispersing it on the surface of paddy fields and the surface of soil. Formulation Example 5. Oil agent Compound No. 1 compound 0.1 part with piperonyl butoxy
Add 0.5 parts of sodium chloride and dissolve in white kerosene to make 100 parts.
And an oil solution was obtained. This product is used as it is. The present invention
The biological effect of the compound represented by the general formula (1)
This will be specifically described with reference to experimental examples. Test Example 1. Effect on diamondback moth
Method) A 20% wettable powder or 20% emulsion of the compound of the present invention is prepared.
It was manufactured according to Examples 1 and 2 and used as a reagent. Test method: cabbage grown on about 10 cabbage true leaves
Cut off the middle leaf of each reagent and the active ingredient of each reagent is 200p
Immerse in the treatment liquid diluted with water to pm for 20 seconds
It was After air-drying, put it in a plastic container with a diameter of 9 cm and
10 third-instar larvae were released. 5-6 small holes in the container
The lid was opened and left in a low temperature room at 25 ° C. place
The number of live and dead insects was investigated 4 days after release, and the mortality rate was calculated.
It was calculated. The results are shown in Table 4 as an average value of duplicates. [Table 4] Test Example 2. Effect on brown planthopper 20% wettable powder or 20% emulsion of the compound of the present invention is prepared.
It was manufactured according to Examples 1 and 2 and used as a reagent. Test method: Each test with 8 strains of 3-4 leaf stage as 1 strain
Dilute with water so that the active ingredient of the drug is 200ppm
It was dipped in the treated solution for 20 seconds. After air drying, diameter 4.5c
It is put in a glass cylinder with a height of 15 cm and a height of 15 cm.
10 third-instar larvae of planthopper were released, and live and dead 6 days after treatment.
The number was investigated and the mortality rate was calculated. The result is the average of two runs
The results are shown in Table 5. [Table 5] The present invention has been described with reference to the embodiments.
It is configured as follows.
Play the fruit. The N-substituted indole derivative of the present invention is
Yes in rice fields, uplands, orchards, forests or environmental hygiene
Effective in pest control scenes.

Claims (1)

What is claimed is: 1. A general formula (1): [Wherein, X represents a CH, N or C- halogen atom,; Y is a hydrogen atom, C ₁ -C ₅ alkyl group, C ₂ -C ₅
Alkenyl group, C ₂ -C ₅ alkynyl group, an alkoxy group, a halogen atom, a cyano group, a nitro group, C ₁ -C ₅ haloalkyl group, C ₁ -C ₅ haloalkoxy group, C ₂ -C
₅ haloalkenyl group or C ₂ -C ₅ haloalkynyl group is shown; R ¹ is C ₁ -C ₅ alkyl group, C ₁ -C ₅ haloalkyl group, C ₁ -C ₅ alkoxy group or C ₁ -C
_{5 represents a} haloalkoxy group; R ² , R ³ and R ⁴ each independently represent a hydrogen atom, a C ₁ -C ₅ alkyl group, C ₂
-C ₅ alkenyl group, C ₂ -C ₅ alkynyl group, a halogen atom, a cyano group, a formyl group, a carboxyl group, an alkoxycarbonyl group, a halo alkoxycarbonyl group, an alkylcarbonyl group, haloalkylcarbonyl group, a nitro group, cyanato group, thiocyanato group, C ₁ -C ₅ haloalkyl group, C ₁ -C ₅ alkoxy group, C ₁ -C ₅ haloalkoxy group, C ₂ -C ₅ haloalkenyl or -S
(O) kR ₅ (where k represents 0, 1 or 2, and R
₅ unsubstituted C ₁ -C ₅ alkyl or, C ₁ substituted with same or different one or more halogen atoms -
C ₅ alkyl); m represents 0, 1 or 2; n represents 0, 1, 2, 3 or 4]. 2. In the general formula (1), X is N or C-
Represents a halogen atom; Y is a C ₁ -C ₅ alkyl group, C ₁
-C ₅ haloalkyl group, halogen atom, cyano group, nitro group or C ₁ -C ₅ haloalkoxy group; R
¹ represents a C ₁ -C ₅ alkyl group, a C ₁ -C ₅ haloalkyl group, a C ₁ -C ₅ alkoxy group or a C ₁ -C ₅ haloalkoxy group; R ₂ , R ₃ and R ₄ are each independently A hydrogen atom, a C ₁ -C ₅ alkyl group, a C ₂ -C ₅ alkenyl group, a C ₂ -C ₅ alkynyl group, a halogen atom, a cyano group, a carboxy group, an alkoxycarbonyl group, a haloalkoxycarbonyl group, an alkylcarbonyl group, A haloalkylcarbonyl group, a nitro group, a C ₁ -C ₅ haloalkyl group, a C ₁ -C ₅ alkoxy group, a C ₁ -C ₅ haloalkoxy group, a C ₂ -C ₅ haloalkenyl group; m is 0, 1 or 2 And n is 0, 1, 2, 3, or 4]. 3. A general formula (2): [Wherein X, Y, R ² -R ⁴ and n have the same meaning as defined in claim 1]. 4. A general formula (3): A compound represented by the formula: wherein R ¹ , R ² , R ³ n and m have the same meaning as defined in claim 1. 5. A compound represented by the general formula (2) is reacted with a sulfinyl halide R ¹ S-halogen atom (wherein R ¹ is alkyl or haloalkyl) in an organic solvent, optionally in the presence of a base. The method for producing the compound of the general formula (1), wherein 6. A general formula (4): [Wherein R ² , R ³ and n have the same meanings as defined in claim 1] and a halogenated sulfinyl R ¹ S-halogen atom (wherein R ¹ is alkyl or haloalkyl) A) in an organic solvent, if necessary, in the presence of a base to form an intermediate represented by the general formula (3), and then in the presence of a base, the general formula (5): [Wherein Z represents halogen, X, Y and R ¹ have the same meaning as defined in claim 1], and the compound represented by the general formula (1) Method for producing compound. 7. An insecticidal composition comprising the novel 1-aryl and 1-pyridylindole derivative represented by the general formula (1) according to claim 1 as an active ingredient.