JPH04364167A - Pyridine compound, its production, intermediate thereof and pest control agent containing the same as active ingredient - Google Patents

Abstract

PURPOSE:To provide a novel compound having an excellent pest-controlling activity and useful as a pest control agent. CONSTITUTION:A compound of formula I (R<1> is H, halogen, etc.; R<2> is H, halogen, etc.; R<3> is halogen, etc.; R<1> is H, lower alkyl; R<5> is halogen, lower alkyl, etc.; X is O, S, C(O), etc.; Y is O, S; (l) is 1-5; (m) is 1-3; (n) is 1-4], e.g. 2- chloro-5-(2-chloro-4-phenoxyphenoxy) methylpyridine. The compound of formula I is produced by reacting a phenol derivative of formula II (M is alkali metal, H) with a compound of formula III (A is halogen) in the presence of a base (e.g. NaH) in a solvent at -20 deg.C to the boiling point of the solvent. The compound of formula I has an excellent potency against insect pests belonging to the Hemiptera, Lepidoptera, Diptera, Coleoptera, Trichoptera, Thysanoptera, Orthoptera, Hymenoptera, Aphaniptera, Anoplura, Isoptera, etc.

Description

[Detailed description of the invention]

0001

TECHNICAL FIELD The present invention relates to a novel pyridine compound, a method for producing the same, an intermediate thereof, and a pest control agent containing the same as an active ingredient.

0002

[Prior Art] Until now, it has been known that certain pyridine compounds have pest control effects, for example, in West German Patent No. 2
, No. 516,331.

0003

[Problems to be Solved by the Invention] However, these compounds cannot always be said to be sufficient as effective ingredients for pest control agents.

0004

[Means for Solving the Problems] In view of the above-mentioned circumstances, the present inventors have conducted intensive studies to find a compound having a better pest control effect, and have developed the following general formula.
The present invention was completed based on the discovery that the pyridine compound represented by Chemical Formula 8 (hereinafter referred to as the compound of the present invention) has extremely high juvenile hormone-like activity. That is, the present invention has the following general formula:

[0005]

[Chemical formula 8]

[In the formula, R1 is independently a hydrogen atom, a halogen atom, an alkyl group having 1 to 4 carbon atoms, or a carbon atom 1
- represents a haloalkyl group of 4, an alkoxy group of 1 to 3 carbon atoms, a haloalkoxy group of 1 to 3 carbon atoms, a cyano group or a nitro group, l represents an integer of 1 to 5, R2
independently represents a hydrogen atom, a halogen atom or a methyl group, m represents an integer of 1 to 3, R3 represents a halogen atom or an alkyl group having 1 to 3 carbon atoms, R4 represents a hydrogen atom or a carbon atom 1 ~3 alkyl groups, R
5 independently represents a halogen atom, an alkyl group having 1 to 3 carbon atoms, a haloalkyl group having 1 to 3 carbon atoms, an alkoxy group having 1 to 3 carbon atoms, or a haloalkoxy group having 1 to 3 carbon atoms; , n represents an integer of 1 to 4, and X represents an oxygen atom, a sulfur atom, a group represented by the formula -C(O)-, a group represented by the formula -S(
O)-, a group represented by the formula -S(O)2-, a group represented by the formula -NH-, or a group represented by the formula -CH2-, and Y represents an oxygen atom or a sulfur atom. . ]
The present invention provides a pyridine compound represented by the above, a method for producing the same, an intermediate thereof, and a pest control agent containing the same as an active ingredient.

The compounds of the present invention are markedly different from most conventional insecticides in that they have excellent juvenile hormone-like activity against insects. That is, it exhibits effects such as inhibiting metamorphosis into adult worms, inhibiting egg hatching, and sterilizing adult worms. As a result, the compounds of the present invention can be used against various pests, including pests that have developed resistance to existing insecticides, such as agricultural, forestry, and horticultural pests.
It mainly acts as a growth regulator, sterilizing agent, ovicidal agent, or growth inhibitor against grain storage pests, sanitary pests, etc., and exhibits a high control effect.

In the compound of the present invention represented by the general formula 8, the halogen atoms represented by R1, R2, R3 and R5 are a fluorine atom, a chlorine atom, a bromine atom and an iodine atom,

In the compound of the present invention represented by the general formula 8, the alkyl group having 1 to 4 carbon atoms represented by R1 includes methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group, isobutyl group, tert-butyl group,

The haloalkyl group having 1 to 4 carbon atoms represented by R1 is, for example, a trifluoromethyl group, a difluoromethyl group, a 2-fluoroethyl group, a 1-fluoroethyl group, a 1,2-difluoroethyl group. ,2,2,2
-Trifluoroethyl group, 2-chloroethyl group, 3-fluoropropyl group, 2-fluoropropyl group, 1-fluoropropyl group, 3-chloropropyl group, 3-bromopropyl group, 4-fluorobutyl group, 4-chlorobutyl group base etc.,

Carbon atom 1 represented by R1 and R5
~3 alkoxy groups are methoxy group, ethoxy group,
n-propoxy group, isopropoxy group,

001
2] The haloalkoxy group having 1 to 3 carbon atoms represented by R1 and R5 is, for example, trifluoromethoxy group, difluoromethoxy group, bromodifluoromethoxy group, 2-fluoroethoxy group, 2,2,2- Trifluoroethoxy group, 1-fluoroethoxy group, 1,2-difluoroethoxy group, 3-fluoro-n-propoxy group, 2-fluoro-n-propoxy group, 1-fluoro-n
-propoxy group, 2-chloroethoxy group, 3-chloro-
n-propoxy group, 3-bromo-n-propoxy group, 1
, 1,2,2-tetrafluoroethoxy group, 1,1-difluoromethoxy group, etc.

The alkyl group having 1 to 3 carbon atoms represented by R3, R4 and R5 is a methyl group, ethyl group, n-propyl group or isopropyl group,

00
14] The haloalkyl group having 1 to 3 carbon atoms represented by R3 is, for example, a trifluoromethyl group, a difluoromethyl group, a 2-fluoroethyl group, a 1-fluoroethyl group, a 1,2-difluoroethyl group, 2,2,2-trifluoroethyl group, 2-chloroethyl group, 3-fluoro-n-propyl group, 2-fluoro-n-propyl group, 1
-fluoro-n-propyl group, 3-chloro-n-propyl group, 3-bromo-n-propyl group, etc.

001
5] Among the compounds of the present invention represented by the general formula 8, R1 is independently a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, a methyl group or a trifluoromethyl group, and l is 1 or 2. , R2 is a hydrogen atom or a chlorine atom, m is 1, R3 is a fluorine atom, chlorine atom, bromine atom or a methyl group, R4 is a hydrogen atom or a methyl group, R5 is independently a chlorine atom or a methyl group, n
is 1 or 2, X is an oxygen atom or a methylene group, and Y is an oxygen atom. More preferable compounds include R
1 is hydrogen atom, fluorine atom or chlorine atom, l is 1 or 2, R2 is hydrogen atom, m is 1, R3 is chlorine atom, R4 is hydrogen atom, R5 is chlorine atom or methyl group, n is 1, X is An oxygen atom or a methylene group, and Y can be an oxygen atom. Even more preferably, (R
1) l is a fluorine atom (2,4-F2) at both the 2nd and 4th positions, a fluorine atom (3,5-F2) at both the 3rd and 5th positions, and a fluorine atom (3,5-F2) at the 3rd and 4th positions. Both are chlorine atom (3,4-Cl2), the 3rd position is a fluorine atom (3-F) or the 3rd position is a chlorine atom (3-Cl), R2 is a hydrogen atom, m is 1, R3
is a chlorine atom, R4 is a hydrogen atom, R5 is a chlorine atom or a methyl group, n is 1, X is an oxygen atom or a formula -CH2
The group represented by - and Y can be an oxygen atom. In addition,
When X is a group represented by the formula -CH2-, R1 may preferably be a hydrogen atom. Most preferably, (R1)l is a fluorine atom (2,4-
F2), both the 3rd and 5th positions are fluorine atoms (3,5-F2), or the 3rd position is a chlorine atom (3,5-F2),
3-Cl), R2 is a hydrogen atom, m is 1, R3 is a chlorine atom, R4 is a hydrogen atom, R5 is a chlorine atom or a methyl group, n is 1, X is an oxygen atom or a group represented by the formula -CH2 -, Y can be an oxygen atom. In addition,
When X is a group represented by the formula -CH2-, (R1)l
It is also preferable that the substitution position at the 3-position is a fluorine atom (3-F). In the compound of the present invention represented by the general formula 8, (
Preferred substitution positions of the phenyl group containing X which may be substituted with R1)l include the 4-position or the 5-position. Preferred substitution positions of the pyridine ring which may be substituted with (R5)n include the 4-position and the 5-position. More preferably, 5th place can be given. Preferred substitution positions for (R5)n are:
I can give you 2nd place.

The compound of the present invention represented by the general formula 8 can be produced, for example, by the following method.

(Production method A) General formula: Chemical formula 9

[0018]

[Chemical formula 9]

[In the formula, R1, R2, R3, X, Y
, l and m have the same meanings as above, and M represents an alkali metal atom or a hydrogen atom. ] and the general formula 10

[0020]

[Chemical formula 10]

[In the formula, R4, R5 and n represent the same meanings as above, and A represents a halogen atom. ] It can be produced by reacting with the compound shown below.

The above reaction is preferably carried out in an inert solvent in the presence of a suitable base. However, when M is an alkali metal atom, the presence of a base is not necessarily required.

Examples of the solvent used include methanol, ethanol, propanol, isopropanol,
Lower alcohols such as tertiary butyl alcohol, ketones such as acetone and methyl ethyl ketone, hydrocarbons such as benzene, hexane and toluene, ethers such as diethyl ether, diisopropyl ether, tetrahydrofuran and dioxane, N,N- Examples include amides such as dimethylformamide and hexamethylphosphoric triamide, halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane, and chlorobenzene, acetonitrile, nitromethane, dimethylsulfoxide, and water. A mixed solvent of these solvents can also be used if necessary.

Examples of the base used include caustic alkalis such as caustic potash and caustic soda, alkali carbonates such as potassium carbonate, alkali metals such as sodium metal, hydrides of alkali metals such as sodium hydride, sodium methoxide, and sodium ethoxylate. Examples include organic bases such as triethylamine, triethylamine, and pyridine. Further, if necessary, a catalyst such as an ammonium salt (for example, triethylbenzylammonium chloride, etc.) may be added to the reaction system.

[0025] The reaction temperature can usually range from -20°C to the boiling point of the solvent used in the reaction, but -5°C
More preferably, the temperature is from

Although the molar ratio of the raw materials and base to be subjected to the reaction can be set arbitrarily, it is advantageous to carry out the reaction at an equimolar ratio or a ratio close to it.

After completion of the reaction, the reaction solution can be subjected to conventional post-treatments such as organic solvent extraction and concentration to obtain the desired compound of the present invention. If necessary, it can be purified by conventional operations such as chromatography, distillation, recrystallization, etc.

(Production method B) General formula: Chemical formula 11

0029
]

[Chemical formula 11]

[In the formula, R1, R2, R3, X, l
and m represent the same meaning as above. ] Phenol derivatives represented by formula 12

[0031]

[Chemical formula 12]

[In the formula, R4, R5 and n represent the same meanings as above. It can be produced by reacting with an alcohol derivative shown in ].

The above reaction is particularly advantageous when R4 is not a hydrogen atom, and the reaction is preferably carried out in the presence of a suitable dehydrating catalyst or dehydrating agent, if necessary, in an inert solvent.

Examples of dehydration catalysts used include inorganic salts such as hydrochloric acid and sulfuric acid, aromatic sulfonic acids and sulfonic acid chlorides, and examples of dehydration agents include dicyclohexylcarbodiimide and diisopropylazodicarboxylate. and diethyl azodicarboxylate.

Examples of the solvent used include hydrocarbons such as benzene, xylene and toluene, diethyl ether, diisopropyl ether, tetrahydrofuran,
Examples include ethers such as dioxane, and halogenated hydrocarbons such as carbon tetrachloride, dichloromethane, chlorobenzene, and dichlorobenzene.

The reaction temperature can range from -20°C to 200°C or the boiling point of the solvent used in the reaction.

Although the molar ratio of the raw materials and dehydrating agent to be subjected to the reaction can be set arbitrarily, it is advantageous to carry out the reaction at an equimolar ratio or a ratio close to it.

After completion of the reaction, the reaction solution can be subjected to conventional post-treatments such as organic solvent extraction and concentration to obtain the desired compound of the present invention. If necessary, it can be purified by conventional operations such as chromatography, distillation, recrystallization, etc.

Furthermore, among the compounds of the present invention, in the case of compounds having an asymmetric carbon atom, the compounds of the present invention can be used in the respective optically active isomers ((+)-isomer, (-
)-body) and mixtures thereof in all proportions.

General formula (9) as a raw material for the compound of the present invention
Among the phenol derivatives represented by the above, the phenol derivative in which M represents a hydrogen atom can be synthesized from the phenol derivative represented by the general formula 11 by a conventional method. For example, it can be produced by the following method (reaction formula 13).

[0041]

[Chemical formula 13]

[0042] Among the above, in the reaction shown by the reaction formula 13, especially when R3 represents a chlorine atom, the reaction shown by the general formula 14

[0043]

[Chemical formula 14]

[In the formula, R1, R2, l and m have the same meanings as above. ] By reacting the phenol derivative represented by the formula with a chlorinating agent in the presence of a solvent, the general formula 15 is obtained.

[0045]

[Chemical formula 15]

[In the formula, R1, R2, l and m have the same meanings as above. ] It can also be obtained according to the usual method of synthesizing the phenol derivative shown.

In the above reaction formula, chlorine, t-butyl hypochlorite, sulfuryl chloride, etc. can be used as the chlorinating agent. Further, a solvent can be used as necessary, and examples of the solvent that can be used include dichloromethane, dichloroethane, carbon tetrachloride, benzene, acetic acid, and the like. It goes without saying that the solvent used here is selected depending on the type of chlorinating agent. The reaction temperature is
The range can be from -78°C to the boiling point of the solvent or chlorinating agent (sulfuryl chloride, etc.) used in the reaction, but -
The range is preferably from 20°C to the boiling point of the solvent or chlorinating agent (such as sulfuryl chloride) used in the reaction. Although the molar ratio of the raw materials and chlorinating agent to be subjected to the reaction can be set arbitrarily, it is advantageous to carry out the reaction at an equimolar ratio or a ratio close to it. After the reaction is completed, the reaction solution can be subjected to conventional post-treatments such as organic solvent extraction and concentration to obtain the target compound. If necessary, chromatography, distillation,
It can also be purified by conventional operations such as recrystallization.

[0048] The phenol derivative represented by the general formula 14 can be produced using a commercially available one or from a commercially available compound, for example, by the method shown below (reaction formulas 16 to 18). can do.

[0049]

[Chemical formula 16]

[0050]

[Chemical formula 17]

[0051]

[Chemical formula 18]

Next, Tables 1 to 33 show compounds of the present invention that can be produced according to these production methods. However, these compounds are for illustrative purposes only, and the present invention is not limited thereto.

[0053]

[Table 1]

[0054]

[Table 2]

[0055]

[Table 3]

[0056]

[Table 4]

[0057]

[Table 5]

[0058]

[Table 6]

[0059]

[Table 7]

[0060]

[Table 8]

[0061]

[Table 9]

[0062]

[Table 10]

[0063]

[Table 11]

[0064]

[Table 12]

[0065]

[Table 13]

[0066]

[Table 14]

[0067]

[Table 15]

[0068]

[Table 16]

[0069]

[Table 17]

[0070]

[Table 18]

[0071]

[Table 19]

[0072]

[Table 20]

[0073]

[Table 21]

[0074]

[Table 22]

[0075]

[Table 23]

[0076]

[Table 24]

[0077]

[Table 25]

[0078]

[Table 26]

[0079]

[Table 27]

[0080]

[Table 28]

[0081]

[Table 29]

[0082]

[Table 30]

[0083]

[Table 31]

[0084]

[Table 32]

[0085]

[Table 33]

[0086] Examples of pests against which the compounds of the present invention are effective include the following.

Hemiptera pests: planthoppers such as the brown planthopper, white-backed planthopper, and brown planthopper, leafhoppers such as the black-spotted leafhopper, black-spotted leafhopper, black-spotted leafhopper, brown leafhopper, brown leafhopper, black-and-white leafhopper, cotton aphid, green peach aphid, etc. Aphids, stink bugs, whiteflies such as tobacco whitefly, and whitefly, scale insects, ground beetles, psyllids, etc.

[0088] Lepidopteran insect pests, such as the Japanese caterpillar moth (Nikamaichu), the brown borer moth, and the Japanese armyworm moth; Pests of the genus Agrotis (A
grothis spp. ), Heliotis spp. (
Heliothis spp. ), diamondback moth, burr moth, carp moth, etc.

[0089] Diptera pests Culex mosquitoes such as Culex Culex and Culex pipiens, Aedes mosquitoes such as Aedes aegypti and Aedes albopictus, Anopheles mosquitoes such as Aedes albopictus, Chironomid mosquitoes, house flies such as house flies and giant house flies, black flies, black flies, red flies, seed flies, Hana flies such as onion flies, fruit flies, fruit flies, fruit flies, fruit flies,
Butterflies, horseflies, blackflies, stable flies, etc.

009
0] Coleoptera Pests Corn rootworms such as Western corn rootworm and Southern corn rootworm, scarab beetles such as the American corn rootworm and Japanese corn rootworm, weevils such as the corn weevil, rice weevil, and bean weevil, and meal beetles such as the brown rice beetle and the brown corn rootworm spp., potato beetles such as the yellow flea beetle and cucumber beetles, leaf beetles, Epilachna spp.

[0091] Ophthalmoptera pests: German cockroach, black cockroach, American cockroach, brown cockroach, small cockroach, etc.

[0092] Synopteran pests such as southern yellow thrips, brown brown thrips, and red thrips

Hymenoptera pests Ants, sawflies such as sawflies, etc.

Orthoptera pests Mole crickets, grasshoppers, etc.

0095: Cryptopteran pests Human flea etc.

0096 Pests of the Order Pyridae Human lice, pubic lice, etc.

[0097] It is effective against isopteran pests such as the Japanese termite and the domestic termite. Furthermore, among these, it is more suitable for controlling Hemiptera pests, and is particularly effective against planthoppers and leafhoppers that damage rice crops, and exhibits an excellent control effect.

[0098] By adding other insecticides and/or acaricides, the compound of the present invention can be practically applied for controlling pests to a wider variety of pests and to a more diverse range of use situations. Suitable additives include, for example, BPMC[2
-sec -butylphenylmethylcarbamate], benfuracarb[ethyl N-[2,3-dihydro-2
, 2-dimethylbenzofuran-7-yloxycarbonyl(methyl)aminothio]-N-isopropyl-β-alaninate], propoxur [2-isopropoxyphenyl N-methylcarbamate], carbosulfan [2,3-dihydro-2 ,2-dimethyl-7-benzo[
b] Furanyl N-dibutylaminothio-N-methylcarbamate], carbaryl [1-naphthyl-N-methylcarbamate], methomyl [S-methyl-N-[(methylcarbamoyl)oxy]thioacetimidate],
Ethiophenecarb [2-(ethylthiomethyl)phenylmethylcarbamate], aldicarb [2-methyl-
Carbamate compounds such as 2-(methylthio)propionaldehyde O-methylcarbamoyloxime], oxamyl [N,N-dimethyl-2-methylcarbamoyloxyimino-2-(methylthio)acetamide],

[
Ethofenprox [2-(4-ethoxyphenyl)-2-methylpropyl-3-phenoxybenzyl ether], fenvalerate [(RS)-α-cyano-3-phenoxybenzyl (RS)-2-(4 -chlorophenyl)-3-methylbutyrate], esfenvalerate [(S)-α-cyano-3-phenoxybenzyl(S)-2-(4-chlorophenyl)-3-methylbutyrate], fenpropathrin [ (RS)-α-cyano-3-phenoxybenzyl 2,2,3,3-tetramethylcyclopropanecarboxylate], Cypermethrin [(RS)-α-cyano-3-phenoxybenzyl (1RS,3RS)-( 1RS, 3RS)-3-(2,
2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate], permethrin [3-phenoxybenzyl(1RS,3RS)-(1RS,3RS)-3
-(2,2-dichlorovinyl)-2,2-methylcyclopropanecarboxylate], cyhalothrin [(RS)
-α-cyano-3-phenoxybenzyl (Z)-(1R
S,3RS)-3-(2-chloro-3,3,3-trifluoropropenyl)-2,2-dimethylcyclopropanecarboxylate], deltamethrin [(S)-α-cyano-m-phenoxybenzyl (1R ,3R)-3(2
, 2-dibromovinyl)-2-dimethylcyclopropanecarboxylate], cycloprothrin [(RS)-α
-cyano-3-phenoxybenzyl (RS)-2,2-
pyrethroid compounds such as dichloro-1-(4-ethoxyphenyl)cyclopropanecarboxylate],

Buprofezin (2-tert-butylimino-3-isopropyl-5-phenyl-1,3,5-
thiadiazine derivatives such as triadiazin-4-one],
Nitroimidazolidine derivatives such as imidacloprid [1-(6-chloro-3-pyridylmethyl)-N-nitroimidazolidin-2-ylideneamine], cartap [S
, S'-(2-dimethylaminotrimethylene)bis(thiocarbamate)], thiocyclam [N,N-dimethyl-1,2,3-trithian-5-ylamine], bensultap [S,S'-2-dimethyl aminotrimethylene di(benzenethiosulfonate)], endosulfan [6,7,8,9,10
,10-hexachloro-1,5,5a,6,9,9a-
hexahydro-6,9-methano-2,4,3-benzodioxathiepine-3-oxide], γ-BHC[1,
Chlorinated hydrocarbon compounds such as 2,3,4,5,6-hexachlorocyclohexane], chlorfluavron [1-(
3,5-dichloro-4-(3-chloro-5-trifluoromethylpyridin-2-yloxy)phenyl]-3-
(2,6-difluorobenzoyl)urea], teflubenzuron [1-(3,5-dichloro-2,4-difluorophenyl)-3-(2,6-difluorobenzoyl)
urea], flufenoxuron [1-[4-(2-chloro-4-trifluoromethylphenoxy)-2-fluorophenyl]-3-(2,6-difluorobenzoyl)
urea], amitraz [N,N'[(methylimino)dimethylidine]di-2,4-xylidine], chlordimeform [N'-(
Formamidine derivatives such as (4-chloro-2-methylphenyl)-N,N-dimethylmetanimidamide] and the like can be mentioned.

When the compound of the present invention is used as an active ingredient of a pest control agent, it may be used as it is without adding any of the ingredients described above, but it is usually used in combination with a solid carrier, liquid carrier, gaseous carrier, or bait. If necessary, surfactants and other formulation auxiliaries are added to produce flowable agents such as oils, emulsions, wettable powders, suspensions and emulsions in water, granules, powders, etc.
It is used in formulations such as aerosols, heating smokers such as self-combustion type smokers, chemical reaction type smokers, and porous ceramic plate smokers, ULV agents, and poison baits.

These preparations usually contain the compound of the present invention as an active ingredient in a weight ratio of 0.001% to 95%. Solid carriers used in formulation include, for example, clays (kaolin clay, diatomaceous earth, synthetic hydrated silicon oxide, bentonite, fubasami clay, acid clay, etc.), talcs, ceramics, and other inorganic minerals (sericite, quartz,
Sulfur, activated carbon, calcium carbonate, hydrated silica, etc.), chemical fertilizers (ammonium sulfate, ammonium phosphorus, ammonium nitrate, urea, ammonium chloride, etc.), and other fine powders or granules.As liquid carriers, for example, water, alcohol, etc. (methanol, ethanol, etc.), ketones (acetone, methyl ethyl ketone, etc.), aromatic hydrocarbons (benzene, toluene, xylene, ethylbenzene, methylnaphthalene, etc.), aliphatic hydrocarbons (hexane, cyclohexane, kerosene, light oil, etc.) ), esters (
ethyl acetate, butyl acetate, etc.), nitriles (acetonitrile, isobutyronitrile, etc.), ethers (diisopropyl ether, dioxane, etc.), acid amides (N, N
-dimethylformamide, N,N-dimethylacetamide, etc.), halogenated hydrocarbons (dichloromethane, trichloroethane, carbon tetrachloride, etc.), dimethyl sulfoxide, vegetable oils such as soybean oil, cottonseed oil, etc.; Examples of the agent include chlorofluorocarbon gas, butane gas, LPG (liquefied petroleum gas), dimethyl ether,
Examples include carbon dioxide gas.

Examples of surfactants include alkyl sulfate esters, alkyl sulfonates, alkylaryl sulfonates, alkylaryl ethers and their polyoxyethylenic products, polyethylene glycol ethers, polyhydric alcohol esters, and sugar alcohols. Examples include derivatives.

[0104] Examples of formulation auxiliaries such as fixing agents and dispersants include casein, gelatin, polysaccharides (starch powder,
Gum arabic, cellulose derivatives, alginic acid, etc.), lignin derivatives, bentonite, sugars, synthetic water-soluble polymers (polyvinyl alcohol, polyvinylpyrrolidone, polyacrylic acids, etc.), etc. Stabilizers include PAP (acidic phosphoric acid, etc.). isopropyl), BHT (2,
6-di-tert-butyl-4-methylphenol),
Examples include BHA (a mixture of 2-tert-butyl-4-methoxyphenol and 3-tert-butyl-4-methoxyphenol), vegetable oil, mineral oil, surfactants, fatty acids or esters thereof, and the like.

[0105] Examples of base materials for self-combusting smoke agents include nitrates, nitrites, guanidine salts, potassium chlorate,
Combustion exothermic agents such as nitrocellulose, ethyl cellulose, and wood flour; thermal decomposition stimulants such as alkali metal salts, alkaline earth metal salts, dichromates, and chromates; oxygen supply agents such as potassium nitrate; melamine, wheat starch, etc. Examples include combustion supporting agents, fillers such as diatomaceous earth, and binders such as synthetic glues. Examples of base materials for chemically reactive smoke agents include alkali metal sulfides, polysulfides, hydrosulfides, hydrated salts,
Exothermic agents such as calcium oxide, carbonaceous substances, iron carbide, catalyst agents such as activated clay, organic blowing agents such as azodicarbonamide, benzenesulfonylhydrazine, dinitrosopentamethylenetetramine, polystyrene, polyurethane, natural fiber pieces, synthetic fibers Examples include fillers such as pieces.

Poison bait base materials include, for example, grain flour, vegetable essential oil, sugar, bait components such as crystalline cellulose, antioxidants such as dibutylhydroxytoluene and nordihydroguaiaretic acid, preservatives such as dehydroacetic acid, and chili pepper. Examples include agents to prevent accidental ingestion of powder, etc., and attractive flavorings such as cheese flavoring and onion flavoring.

The formulation of flowables (suspensions or emulsions in water) generally contains 1 to 75% of the compound in a proportion of 0.5 to 1
5% dispersant, 0.1-10% suspension aid (e.g.
compounds that impart protective colloids and thixotropic properties),
In water containing 0 to 1.0% of suitable adjuvants (e.g. antifoaming agents, rust inhibitors, stabilizers, spreading agents, penetration aids, antifreeze agents, antibacterial agents, antismoke agents, etc.) It can be obtained by finely dispersing it. It is also possible to use an oil in which the compound hardly dissolves in place of water to form a suspension in oil. As the protective colloid, for example, gelatin, casein, gums, cellulose ether, polyvinyl alcohol, etc. are used. Examples of compounds that impart thixotropy include bentonite, aluminum magnesium silicate, xanthan gum, and polyacrylic acid.

[0108] The preparation thus obtained is used as it is or diluted with water or the like. Also, other insecticides,
It can also be used simultaneously with or without mixing with nematicides, acaricides, fungicides, herbicides, plant growth regulators, synergists, fertilizers, soil conditioners, animal feed, etc.

When the compound of the present invention is used as an agricultural pest control agent, the application amount is usually 0.001 g to 500 g per 10 ares, preferably 0.1 g.
g to 500 g. When using emulsions, wettable powders, flowables, etc. diluted with water, the application concentration is usually 0.
．． 0001ppm to 1000ppm, granules,
Powders and the like should be applied in their original form without any dilution. In addition, when used as pest control agents for epidemic prevention, emulsions, hydrating agents, flowable agents, etc. are usually 0.0001
Apply diluted to ppm ~ 10,000 ppm, oil agent,
Aerosols, smoke agents, ULV agents, poison baits, etc. should be applied as is.

[0110] These application amounts and concentrations vary depending on the type of preparation, application time, application location, application method, type of pest, degree of damage, etc., and may be increased or increased without regard to the above range. It can be reduced.

[0111]

EXAMPLES The present invention will be explained in more detail below with reference to production examples, formulation examples, and test examples, but the present invention is not limited to these examples. First, a production example of the compound of the present invention will be shown.

Production Example 1 (Production method for compound (1) of the present invention) 2-chloro-4-
A solution of 0.45 g of phenoxyphenol and 3 ml of dimethylformamide was added dropwise with stirring under ice cooling. After 30 minutes, a solution of 0.34 g of 2-chloro-5-chloromethylpyridine in 5 ml of dimethylformamide was added to the mixture at room temperature, and the mixture was stirred at room temperature. After 10 hours, the reaction solution was poured into ice water and extracted twice with 100 ml of ethyl acetate. The ethyl acetate layers were combined, washed with water, dried, and concentrated to obtain a crude product. This crude product was subjected to silica gel chromatography to obtain 0.50 g of 2-chloro-5-(2-chloro-4-phenoxyphenoxy)methylpyridine. Yield: 71% n22D: 1.6173

0113
Production Example 2 (Production method for compound (33) of the present invention) 2-chloro-4-
(3-trifluoromethylphenoxy)phenol 0.
A solution of 50 g and 3 ml of dimethylformamide is added dropwise with stirring under ice cooling. After 30 minutes, at room temperature,
A solution of 0.28 g of 2-chloro-5-chloromethylpyridine in 5 ml of dimethylformamide is added and stirred at room temperature. After 10 hours, the reaction solution was poured into ice water, and ethyl acetate 1
Extract twice with 00ml. The ethyl acetate layers are combined, washed with water, dried, and concentrated to obtain a crude product. This crude product was subjected to silica gel chromatography, and 2-chloro-5-[
2-chloro-4-(3-trifluoromethylphenoxy)phenoxy]methylpyridine is obtained.

Production Example 3 (Production method for compound (34) of the present invention) 2-chloro-4-
A solution of 0.50 g of (3-bromophenoxy)phenol and 3 ml of dimethylformamide is added dropwise with stirring under ice cooling. After 30 minutes, 2-chloro-
A solution of 0.27 g of 5-chloromethylpyridine in 5 ml of dimethylformamide is added and stirred at room temperature. After 10 hours, the reaction solution was poured into ice water and diluted with 100 ml of ethyl acetate.
Extract times. The ethyl acetate layers are combined, washed with water, dried, and concentrated to obtain a crude product. This crude product is subjected to silica gel chromatography to obtain 2-chloro-5-[4-(3-bromophenoxy)-2-chlorophenoxy]methylpyridine.

Production Example 4 (Production method for compound (17) of the present invention) 0.82 g of 2-chloro-5-phenoxyphenol, 2
-Methyl-5-hydroxymethylpyridine 0.54g,
Triphenylphosphine 1.01 g, diethyl azadicarboxylate 0.65 g and tetrahydrofuran 9
0 ml was placed in a reaction vessel and stirred at room temperature. After 48 hours, the reaction solution was concentrated, 50 ml of diethyl ether was added, and the precipitate was filtered. After concentrating the filtrate, it was subjected to silica gel chromatography.
0.66 g of 2-methyl-5-[2-chloro-5-phenoxyphenoxy]methylpyridine was obtained. Yield: 51% mp: 64.9℃

Production Example 5 (Production method of compound (35) of the present invention) 0.80 g of 2-chloro-5-phenoxyphenol, 2
-Chloro-5-(1-hydroxyethyl)pyridine 0.
57 g, triphenylphosphine 0.95 g, diethyl azadicarboxylate 0.63 g and tetrahydrofuran 100 ml were placed in a reaction vessel and stirred at room temperature. After 48 hours, the reaction solution was concentrated and added with 50 ml of diethyl ether.
Add gel and filter the precipitate. After concentrating the filtrate, it was subjected to silica gel chromatography to obtain 2-chloro-5-[1
-(2-chloro-4-phenoxyphenoxy)ethyl]
Get pyridine. Next, some of the compounds of the present invention obtained according to these production methods are shown in Tables 34 to 41.

[0117]

[Table 34]

[0118]

[Table 35]

[0119]

[Table 36]

[0120]

[Table 37]

[0121]

[Table 38]

[0122]

[Table 39]

[0123]

[Table 40]

[0124]

[Table 41]

Next, an example of intermediate production will be shown. Production Example 6 (Production of intermediate compound (42) of the compound of the present invention) p-(3,5-difluorophenoxy)phenol5.
0 g was dissolved in 50 ml of carbon tetrachloride, and while stirring vigorously under ice cooling, 2.45 g of t-butyl hypochlorite was slowly added dropwise. After the dropwise addition was completed, the mixture was stirred at room temperature. After 5 hours, the reaction solution was concentrated, 200 ml of ethyl acetate was added to the residue, and the mixture was washed with 5% aqueous sodium bicarbonate. After drying and concentrating the ethyl acetate solution, the residue was subjected to silica gel chromatography to obtain 5.31 g of 2-chloro-4-(3,5-difluorophenoxy)phenol. Yield: 92% n25D: 1.5639 Next, Tables 42 to 45 show some of the intermediate compounds of the compounds of the present invention obtained according to these production methods.

[0126]

[Table 42]

[0127]

[Table 43]

[0128]

[Table 44]

[0129]

[Table 45]

[0130] Next, formulation examples will be shown. In addition, parts represent parts by weight, and the compounds of the present invention are represented by compound numbers listed in Tables 34 to 41.

Formulation Example 1 Emulsion 10 parts each of the compounds (1) to (40) of the present invention were dissolved in 35 parts of xylene and 35 parts of dimethylformamide, and 14 parts of polyoxyethylene styrylphenyl ether and dodecylbenzenesulfonic acid were dissolved therein. calcium 6
and stir well to obtain each 10% emulsion.

Formulation Example 2 Wettable powder 20 parts each of the compounds (1) to (40) of the present invention were mixed with 4 parts of sodium lauryl sulfate, 2 parts of calcium lignin sulfonate, 20 parts of synthetic hydrated silicon oxide fine powder, and 5 parts of silicon earth.
Add 4 parts to the mixture and stir and mix with a juice mixer to obtain a 20% hydrating powder.

Formulation Example 3 Granules Compounds of the present invention (1), (2), (7), (10), (1
3) Add 5 parts of sodium dodecylbenzenesulfonate, 30 parts of bentonite, and 60 parts of clay to 5 parts each of (15), (19), (30), and (37), and mix thoroughly with stirring. Then add appropriate amount of water to these mixtures,
The mixture is further stirred, granulated using a granulator, and dried through ventilation to obtain 5% granules.

Formulation Example 4 Granules Compounds of the present invention (3) to (6), (8), (9), (11
), (12), (16) ~(18), (20) ~(
29), (31), (32), (38) to 5 parts each of (40), 5 parts of synthetic hydrated silicon oxide fine powder, 5 parts of sodium dodecylbenzenesulfonate, 30 parts of bentonite, and 55 parts of clay were added. Stir thoroughly to mix. Then,
An appropriate amount of water is added to the mixture, which is further stirred, granulated using a granulator, and dried through ventilation to obtain 5% granules.

Formulation Example 5 Powder Compounds of the present invention (1), (2), (7), (10), (1
3) - 0.3 parts each of (15), (19), (30), (37), 1 part of synthetic hydrated silicon oxide fine powder, 1 part of Drilless B (trade name manufactured by Sankyo Co., Ltd.) as a flocculant, clay After thoroughly mixing 7.7 parts in a mortar, stir and mix with a juice mixer. Add 90 parts of cut clay to the resulting mixture,
Mix the bags to obtain each 0.3% powder.

Formulation Example 6 Powder Compounds of the present invention (3) to (6), (8), (9), (11
), (12), (16) ~(18), (20) ~(
0.3 parts each of 29), (31), (32), (38) to (40) and 0.03 part of synthetic hydrated silicon oxide fine powder were thoroughly stirred and mixed with a juice mixer, and then ground with a centrifugal grinder. do. To the obtained pulverized mixture were added 0.97 parts of synthetic hydrous silicon oxide fine powder, 1 part of the trade name Driles B (manufactured by Sankyo Co., Ltd.) as a flocculant, and 7.7 parts of clay, and after mixing well in a mortar, the mixture was mixed in a juice mixer. Stir to mix. 90 parts of cut clay was added to the resulting mixture and mixed in a bag to obtain each 0.3% powder.

Formulation Example 7 Powder Compounds of the present invention (1), (2), (7), (10), (1
3) to 0.3 parts each of (15), (19), (30), and (37), BPMC(O-
2 parts of sec -butylphenyl N-methylcarbamate), 3 parts of synthetic hydrous silicon oxide fine powder, 1 part of brand name Driles B (manufactured by Sankyo Co., Ltd.) as a coagulant, and 3.7 parts of clay were thoroughly mixed in a mortar, and then the juice was mixed. Stir and mix with a mixer. Add 90 parts of cut clay to the resulting mixture,
Mix the bags to obtain each powder.

Formulation Example 8 Powder Compounds of the present invention (3) to (6), (8), (9), (11
), (12), (16) ~(18), (20) ~(
0.3 parts each of 29), (31), (32), (38) to (40) and 0.03 part of synthetic hydrated silicon oxide fine powder were thoroughly stirred and mixed with a juice mixer, and then ground with a centrifugal grinder. do. BPMC (O-sec-butylphenyl N
- 2 parts of methyl carbamate), 2.97 parts of synthetic hydrous silicon oxide fine powder, 1 part of brand name Driles B (manufactured by Sankyo Co., Ltd.) as a coagulant, and 3.7 parts of clay were mixed well in a mortar, and then mixed with a juice mixer. Stir to mix. 90 parts of cut clay was added to the resulting mixture and mixed in a bag to obtain each powder.

Formulation Example 9 Powder One part of each of the compounds (1) to (40) of the present invention was dissolved in an appropriate amount of acetone, and 5 parts of synthetic hydrated silicon oxide fine powder,
Add 0.3 parts of PAP and 93.7 parts of clay, stir and mix using a juice mixer, and remove acetone by evaporation to obtain 1% powder of each.

Formulation Example 10 Flowable agent Compounds of the present invention (1), (2), (7), (10), (13) to (15)
), (19), (30), and (37) were added to 40 parts of an aqueous solution containing 6 parts of polyvinyl alcohol,
Stir with a mixer to obtain a dispersant. Add 40 parts of an aqueous solution containing 0.05 part of xanthan gum and 0.1 part of aluminum magnesium silicate to this, and further add 10 parts of propylene glycol and mix with gentle stirring to obtain each 10% emulsion in water. .

Formulation Example 11 Flowable agent Compounds of the present invention (3) to (6), (8), (9), (11), (12)
, (16) to (18), (20) to (29), (3
1), (32), (38) to (40) and 1.5 parts of sorbitan trioleate were mixed with 28.5 parts of an aqueous solution containing 2 parts of polyvinyl alcohol, and pulverized with a sand grinder ( (particle size of 3μ or less), 40 parts of an aqueous solution containing 0.05 part of xanthan gum and 0.1 part of aluminum magnesilicate was added thereto, and 10 parts of propylene glycol was further added and mixed with stirring.
A 0% suspension in water is obtained.

Formulation Example 12 Oil Agent 0.1 part of each of the compounds (1) to (40) of the present invention was dissolved in 5 parts of xylene and 5 parts of trichloroethane, and this was mixed with 89.9 parts of deodorized kerosene. Obtain % oil solution.

Formulation Example 13 Oil-based aerosol 0.1 part each of the compounds (1) to (40) of the present invention, 0 tetramethrin
．． After mixing and dissolving 2 parts of d-phenothrin, 0.1 parts of trichloroethane, 10 parts of trichloroethane, and 59.6 parts of deodorized kerosene, filling it into an aerosol container and attaching a valve part, propellant (liquefied petroleum gas) is passed through the valve part. Fill 30 parts under pressure to obtain an oil-based aerosol.

Formulation Example 14 Aqueous aerosol 0.2 parts each of the compounds (1) to (40) of the present invention, d-allethrin 0
．． 2 parts of d-phenothrin, 0.2 parts of xylene, 3.4 parts of deodorized kerosene, and 1 part of an emulsifier {Atmos 300 (registered trademark of Atlas Chemical Co., Ltd.)} were mixed and dissolved, and 50 parts of pure were mixed into an aerosol. A container is filled, a valve part is attached, and 40 parts of propellant (liquefied petroleum gas) is pressurized and filled through the valve part to obtain an aqueous aerosol.

Formulation Example 15 Heated smoking agent Compound of the present invention (
100 mg of each of 1) to (40) was dissolved in an appropriate amount of acetone and impregnated into a porous ceramic plate of 4.0 cm x 4.0 cm and 1.2 cm thick to obtain a heated smoking agent.

Next, it will be shown by test examples that the compounds of the present invention are useful as active ingredients of pest control agents. The compounds of the present invention are indicated by the compound numbers listed in Tables 34 to 41, and the compounds used for comparison are indicated by the compound numbers listed in Table 46.

[0147]

[Table 46]

Test Example 1 Metamorphosis inhibitory effect on brown planthopper larvae An emulsion of the test compound obtained according to Preparation Example 1 was diluted with water to a predetermined concentration and applied to rice seedlings planted in polyethylene cups in 20ml/2 pots. It was distributed in proportion. After air drying, 10 brown planthopper 3rd instar larvae were released per pot.
After several days, the inhibition rate of emergence was determined. Tables 47 to 52 show the results.
Shown below.

[0149]

[Table 47]

[0150]

[Table 48]

[0151]

[Table 49]

[0152]

[Table 50]

[0153]

[Table 51]

[0154]

[Table 52]

Test Example 2 Growth inhibitory effect on leafhopper An emulsion of the test compound obtained according to Preparation Example 1 was diluted with water to a predetermined concentration, and rice seedlings (about 20 cm tall) planted in pots (1/5000a) were prepared. ) at a rate of 40 ml/2 pots. After air-drying, the pots were covered with wire mesh gauges, and 10 male and 10 female adult leafhoppers were released per pot, and the pots were left in a greenhouse. After about 3 weeks, the number of surviving nymphs of the next generation was investigated, and the growth inhibition rate was determined. The results are shown in Table 53.

[0156]

[Table 53]

Test Example 3 Growth inhibitory effect on brown planthopper An emulsion of the test compound obtained according to Preparation Example 1 was diluted with water to a predetermined concentration, and rice seedlings (about 20 cm tall) planted in pots (1/5000a) were prepared. ) at a rate of 40 ml/2 pots. After air-drying, the pots were covered with wire mesh gauges, and five male and five female brown planthopper adults were released per pot, and the pots were left in a greenhouse. After about 3 weeks, we investigated the number of surviving nymphs in the next generation.
The growth inhibition rate was determined. The results are shown in Table 54.

[0158]

[Table 54]

Test Example 4 Test against Cotton Aphids An emulsion of the test compound obtained according to Example 1 was diluted with water to a predetermined concentration, and 8 to 9 days after sowing, it was infested with cotton aphid first instar larvae. For cotton planted in pots (initial leaf stage), 3
It was sprayed at a rate of 0 ml/2 pots. The total number of cotton aphids on the plants was investigated before and 7 days after spraying. A pest control effect index was calculated using the following formula to represent the pest control effect. The effectiveness evaluation criteria are A: The control effect index is 1 or less, and the growth inhibitory effect is sufficiently recognized. B: When the control effect index is greater than 1 and less than or equal to 3, a growth inhibitory effect is observed. C: The control effect index is greater than 3, and a slight growth inhibitory effect is observed. D: The control effect index is the same as that of the untreated area, and no growth suppression effect is observed. And so. The results are shown in Table 55.

[0160]

[Table 55]

[0161]

[Effects of the Invention] The compounds of the present invention are effective against Hemiptera pests, Lepidoptera pests, Diptera pests, Coleoptera pests, Reciptate pests, Thymoptera pests, Orthoptera pests, Hymenoptera pests, and cryptopteran pests. It has an excellent control effect on insect pests of the Order order, Prunidae order, Isoptera order pests, etc., and can be used for various purposes as a pest control agent.

Claims (6)

[Claims] Claim 1: General formula: Chemical formula 1: [In the formula, R1 is independently a hydrogen atom, a halogen atom, an alkyl group having 1 to 4 carbon atoms, a haloalkyl group having 1 to 4 carbon atoms, or a carbon atom. represents an alkoxy group having 1 to 3 carbon atoms, a haloalkoxy group having 1 to 3 carbon atoms, a cyano group, or a nitro group, l represents an integer of 1 to 5, and R2 is independently a hydrogen atom, a halogen atom, or a methyl group. , m is 1
represents an integer of ~3, R3 represents a halogen atom or an alkyl group having 1 to 3 carbon atoms, R4 represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and R5 independently represents a halogen atom or an alkyl group having 1 to 3 carbon atoms. represents an alkyl group having 1 to 3 atoms, a haloalkyl group having 1 to 3 carbon atoms, an alkoxy group having 1 to 3 carbon atoms, a haloalkoxy group having 1 to 3 carbon atoms, and n is an integer of 1 to 4. where X is an oxygen atom, a sulfur atom, a group represented by the formula -C(O)-, a group represented by the formula -S(O)-, a group represented by the formula -S(O)2-, a group represented by the formula -NH
It represents a group represented by - or a group represented by the formula -CH2-, and Y represents an oxygen atom or a sulfur atom. ] A pyridine compound represented by [Claim 2] General formula: [Formula 2] [In the formula, R1 is independently a hydrogen atom, a halogen atom, an alkyl group having 1 to 4 carbon atoms, a haloalkyl group having 1 to 4 carbon atoms, or a carbon atom] represents an alkoxy group having 1 to 3 carbon atoms, a haloalkoxy group having 1 to 3 carbon atoms, a cyano group, or a nitro group, l represents an integer of 1 to 5, and R2 is independently a hydrogen atom, a halogen atom, or a methyl group. , m is 1
represents an integer of ~3, R3 represents a halogen atom or an alkyl group having 1 to 3 carbon atoms, X represents an oxygen atom, a sulfur atom, a group represented by the formula -C(O)-, a group represented by the formula -S(O) A group represented by -, a group represented by the formula -S(O)2-, a group represented by the formula -NH
It represents a group represented by - or a group represented by the formula -CH2-, Y represents an oxygen atom or a sulfur atom, and M represents an alkali metal atom or a hydrogen atom. ] Pheno-
[In the formula, R4 represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and R5 independently represents a halogen atom, an alkyl group having 1 to 3 carbon atoms, It represents a haloalkyl group having 1 to 3 carbon atoms, an alkoxy group having 1 to 3 carbon atoms, or a haloalkoxy group having 1 to 3 carbon atoms, n represents an integer of 1 to 4, and A represents a halogen atom. 2. The method for producing a pyridine compound according to claim 1, which comprises reacting the pyridine compound with a compound represented by the following. [Claim 3] General formula: [Formula 4] [In the formula, R1 is independently a hydrogen atom, a halogen atom, an alkyl group having 1 to 4 carbon atoms, a haloalkyl group having 1 to 4 carbon atoms, or a carbon atom] represents an alkoxy group having 1 to 3 carbon atoms, a haloalkoxy group having 1 to 3 carbon atoms, a cyano group, or a nitro group, l represents an integer of 1 to 5, and R2 is independently a hydrogen atom, a halogen atom, or a methyl group. , m is 1
represents an integer of ~3, R3 represents a halogen atom or an alkyl group having 1 to 3 carbon atoms, X represents an oxygen atom, a sulfur atom, a group represented by the formula -C(O)-, a group represented by the formula -S(O) A group represented by -, a group represented by the formula -S(O)2-, a group represented by the formula -NH
Represents a group represented by - or a group represented by the formula -CH2 -. ] and the general formula 5 [
[In the formula, R4 represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and R5 independently represents a halogen atom, an alkyl group having 1 to 3 carbon atoms, or a haloalkyl group having 1 to 3 carbon atoms. group, an alkoxy group having 1 to 3 carbon atoms, and a haloalkoxy group having 1 to 3 carbon atoms, and n represents an integer of 1 to 4. 2. The method for producing a pyridine compound according to claim 1, wherein the pyridine compound is reacted with an alcohol compound represented by the following formula. [Claim 4] General formula: [Chemical formula 6] [In the formula, (R1)l is a fluorine atom (2,4-F2) at both the 2nd and 4th positions, and a fluorine atom (2,4-F2) at both the 3rd and 5th positions. Fluorine atom (3,5-F2), chlorine atom (3,4-Cl2) at both the 3rd and 4th positions
, the substitution position at the 3rd position represents a fluorine atom (3-F) or the substitution position at the 3rd position represents a chlorine atom (3-Cl), R2 represents a hydrogen atom or a chlorine atom, m represents 1, and R3 represents a chlorine atom. represents an atom, X represents an oxygen atom or a group represented by the formula -CH2-, Y represents an oxygen atom, and M represents an alkali metal atom or a hydrogen atom. ] A phenol derivative represented by [Claim 5] General formula: [Chemical formula 7] [In the formula, (R1)l is a fluorine atom (2,4-F2) at both the 2nd and 4th positions, and a fluorine atom (2,4-F2) at both the 3rd and 5th positions. Fluorine atom (3,5-F2), chlorine atom (3,4-Cl2) at both the 3rd and 4th positions
, the substitution position at the 3rd position represents a fluorine atom (3-F) or the substitution position at the 3rd position represents a chlorine atom (3-Cl), R2 represents a hydrogen atom, m represents 1, and R3 represents a chlorine atom. ,
X represents an oxygen atom or a group represented by the formula -CH2-, Y represents an oxygen atom, and M represents an alkali metal atom or a hydrogen atom. ] A phenol derivative represented by 6. A pest control agent comprising the pyridine compound according to claim 1 as an active ingredient.