JP2019081709A - Pest control agent - Google Patents

Abstract

To provide a compound having high activity on pest.SOLUTION: There is provided a substituted pyridine-based compound represented by the formula (I), wherein Ris alkyl or the like, Ris a halogen atom, nitro, alkoxy or the like, L is -CHBrCHBr-, -CHClCHCl-, -CHBrCHCl-, -CHClCHBr-, -CH=CH-, -CH=CCl- or -CH=CBr-, or a salt thereof.SELECTED DRAWING: None

Description

  The present invention relates to a novel substituted pyridine compound or a salt thereof, and a pest control agent containing the compound or a salt thereof as an active ingredient.

  Patent Document 1 describes a compound containing a fluorine atom in a portion corresponding to L in formula (I) described later, and describes that the compound is useful as an agricultural and horticultural insecticide, Invention compounds are not described. In addition, on page 92 of Patent Document 2, 4- [2- (4-bromo-phenyl) -vinyl] -nicotinic acid is described, but this compound is distinguished from the compound of formula (I) described later. Ru.

International Publication No. 2013/158422 WO 2004/043966

  Although many pest control agents have been used for many years, many have various problems such as insufficient efficacy, resistance to pests and the like, and their use being limited. Therefore, there is a need for the development of a novel pest control agent with few such drawbacks. An object of the present invention is to provide a compound having high activity against pests, provide a pest control agent using the compound, and provide a method of controlling the pest by applying the compound. It is to be.

The present inventors variously examined pyridine derivatives in order to find better pesticides. As a result, they have found that the novel substituted pyridine compounds have a very high control effect on pests at low doses, and completed the present invention.
That is, the present invention relates to Formula (I):

[Wherein, R ¹ represents a halogen atom, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, alkoxy, alkenyloxy, alkynyloxy, cycloalkoxy, haloalkoxy, alkylthio, alkenylthio, alkynylthio, cycloalkylthio, Haloalkylthio, alkylamino, alkenylamino, alkynylamino, dialkylamino, dialkenylamino, dialkynylamino, alkylsulfinyl, alkenylsulfinyl, alkynylsulfinyl, cycloalkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, alkenylsulfonyl, alkynylsulfonyl, alkylcarbonyl , Alkoxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl , Alkylcarbonyloxy, alkylcarbonylamino or alkylcarbonylalkylamino;
R ² is a halogen atom, cyano, nitro, alkenyl, alkynyl, cycloalkyl, haloalkyl, hydroxy, alkoxy, haloalkoxy, alkenyloxy, alkynyloxy, cycloalkoxy, alkylthio, alkenylthio, alkynylthio, cycloalkylthio, alkylamino, alkenyl Amino, alkynylamino, dialkylamino, dialkenylamino, dialkynylamino, alkylsulfinyl, alkenylsulfinyl, alkynylsulfinyl, alkylsulfonyl, alkenylsulfonyl, alkynylsulfonyl, alkyloxyalkyl, alkylthioalkyl, alkylaminoalkyl, dialkylaminoalkyl, formyl , Alkylcarbonyl, alkoxycarbonyl, alkylaminocarbonyl , Dialkylaminocarbonyl, alkylcarbonyloxy, alkylcarbonylthio, alkylcarbonylamino or dialkylcarbonylamino;
L is a substituted pyridine compound or a salt thereof, wherein-is -CHBrCHBr-, -CHClCHCl-, -CHBrCHCl-, -CHClCHBr-, -CH = CH-, -CH = CCl- or -CH = CBr-; The present invention relates to a pest control agent containing the compound or a salt thereof as an active ingredient, and a method of controlling a pest by applying an effective amount of the compound or a salt thereof.

  The pest control agent containing the compound of the formula (I) or a salt thereof as an active ingredient has a very high controlling effect on pests at a low dose.

  As a halogen atom in the said Formula (I) or halogen as a substituent, each atom of a fluorine, chlorine, a bromine, or an iodine is mentioned. The number of halogen atoms as a substituent may be one or more, and in the case of two or more, each halogen atom may be the same or different. The substitution position of the halogen atom may be any position.

Examples of the alkyl or alkyl moiety in the formula (I) include methyl, ethyl, normal propyl, isopropyl, normal butyl, isobutyl, secondary butyl, tertiary butyl, normal butyl, isopentyl, neopentyl, normal hexyl, neohexyl and the like. Straight-chain or branched C ₁ -C ₆ groups.
In this specification, "iso" may be described as "i-", "normal" as "n-", "secondary" as "s-", and "tertiary" as "t-". .

The alkenyl or alkenyl moiety in the above formula (I) is, for example, vinyl, 1-propenyl, 2-propenyl, isopropenyl, 2-methyl-1-propenyl, 1-methyl-1-propenyl, 2-methyl-2 -Propenyl, 1-methyl-2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 2-methyl-2-butenyl, 1-hexenyl, 2,3-dimethyl-2 - it includes straight chain or branched chain groups of C _{2-C 6} such as butenyl.

The alkynyl or alkynyl moiety in the above formula (I) is, for example, ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 2-methyl- A linear or branched C ₂ -C ₆ group such as 3-butynyl, 3,3-dimethyl-1-butynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl Can be mentioned.

The cycloalkyl or the cycloalkyl moiety in the formula (I) includes, for example, a C ₃ -C ₆ group such as cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.

  The salts of the compounds of the formula (I) include any salts acceptable in the art, for example, ammonium salts such as dimethylammonium salt and triethylammonium salt; hydrochloride, perchlorine Mineral acid salts such as acid salts, sulfates and nitrates; and organic acid salts such as acetates, trifluoroacetates, oxalates, p-toluenesulfonates and methanesulfonates.

  The compound of the formula (I) or a salt thereof may contain one or more asymmetric centers in its structural formula, and optical isomers or stereoisomers may be present. Includes both isomers and isomer mixtures. In addition, although there may be geometric isomers derived from carbon double bonds for L in formula (I), the present invention also includes each geometric isomer and a mixture in which they are included in any ratio. Do. In the present specification, isomers are described as a mixture unless otherwise stated. The present invention also includes various isomers other than those described above within the scope of the common technical knowledge in the relevant technical field. Further, depending on the type of isomer, the chemical structure may be different from that of the above-mentioned formula (I), but those skilled in the art can sufficiently recognize that they are in the relationship of isomer, so the scope of the present invention It is clear that it is inside.

  The compound of the formula (I) or a salt thereof can be produced according to the following production method as well as a common salt production method, but is not limited to these methods.

Production method [1]
Among the compounds of formula (I) described above, the compounds of formula (I-1) wherein L is -CH = CH- comprises a compound of formula (II) and a compound of formula (III) in the presence of acetic anhydride Can be manufactured by heating.

[Wherein, R ¹ and R ² are as defined above]

This reaction can be carried out in the presence of a solvent, if necessary. Examples of the solvent include, for example, aromatic hydrocarbons such as toluene and xylene.
The reaction temperature is usually in the range of 100 ° C. to the boiling point of the solvent used. The reaction time is usually several hours to 48 hours.

Production method [2]
Among the compounds of the formula (I) described above, the compounds of the formula (I-2) wherein L is -CHBrCHBr-, -CHClCHCl-, -CHBrCHCl- or -CHClCHBr- are compounds of the formula (I-1) and halogen It can be produced by reacting an agent. The halogenating agent used in the production method [2] is a chlorinating agent and / or a brominating agent. In the case of producing a compound in which X ¹ and X ² are different, an interhalogen compound such as bromine monochloride is used as a halogenating agent, and in this case, L is —CHBrCHCl— or —CHClCHBr— 2 A mixture of compounds of formula (I-2) is formed.

[Wherein, R ¹ and R ² are as defined above, and X ¹ and X ² are each independently a chlorine atom or a bromine atom]

This reaction can be carried out in the presence of a solvent, if necessary. Examples of the solvent include aliphatic halogenated hydrocarbons such as dichloromethane and chloroform.
The reaction temperature is usually in the range of 0 ° C. to the boiling point of the solvent used. The reaction time is usually a few minutes to 24 hours.

Production method [3]
Among the compounds of the formula (I) described above, the compounds of the following formula (I-3) and the compound of the formula (I-4) in which L is —CHCHCCl— or —CH = CBr— have the following flow As shown, it can be produced by reacting a compound of formula (I-2) with a base. The production ratio of the compound of formula (I-3) and the compound of formula (I-4) varies depending on the reaction conditions.

[Wherein, R ¹ , R ² , X ¹ and X ² are as defined above]

  Examples of the base include alkali metal hydrides such as sodium hydride; alkali metal carbonates such as potassium carbonate; alkali metal hydroxides such as sodium hydroxide; amines such as triethylamine; and the like. In addition, this reaction can be carried out in the presence of a solvent, if necessary. Examples of the solvent include alcohols such as methanol, ethanol and isopropanol. The reaction temperature is usually in the range of room temperature to the boiling point of the solvent used. The reaction time is usually several hours to 48 hours.

The compound of the formula (II) which is an intermediate for the preparation of the compound of the formula (I) is a known compound or can be prepared according to known literatures.
Intermediate manufacturing method [1]
The compound of the formula (II-a) wherein R ² is OR ³ in the above formula (II) is prepared by reacting 3-amino-4-methylpyridine with R ³ OH with a nitrite in the presence of an acid After reaction, it can be produced by adding a base.

[Wherein, R ³ is alkyl, alkenyl, alkynyl, cycloalkyl or haloalkyl]

  This reaction can be carried out in the presence of a solvent, if necessary. The solvent may be any solvent as long as it is inert to the reaction, and aprotic polar solvents such as acetonitrile and dioxane; water; Can. The reaction temperature is usually in the range of about room temperature to the temperature at which the reaction mixture refluxes. The reaction time is usually a few minutes to 48 hours.

  Examples of the acid include inorganic acids such as hydrochloric acid and sulfuric acid; and organic acids such as methanesulfonic acid. Examples of nitrites include isopropyl nitrite and tert-butyl nitrite. Examples of the base include carbonates of alkali metals such as sodium carbonate and potassium carbonate; hydrogencarbonates of alkali metals such as sodium hydrogencarbonate and potassium hydrogencarbonate; alkoxides such as sodium methoxide and sodium ethoxide Can be mentioned.

Intermediate manufacturing method [2]
In the above formula (II), a compound of the formula (II-b) in which R ² is SR ³ is reacted with 3-amino-4-methylpyridine with an inorganic nitrite or nitrite to form a diazonium compound , R ³ SH or (R ³ S) ₂ can be produced by the Sandmeyer reaction.

[Wherein, R ³ is as defined above]
Examples of the inorganic nitrite include sodium nitrite and potassium nitrite.
Examples of nitrites include tertiary butyl nitrite and isoamyl nitrite.
The reaction can be carried out in the presence of a copper catalyst, if necessary. Examples of copper catalysts include copper (I) oxide and copper (II) sulfate pentahydrate.
The reaction can be carried out in the presence of an acid, if necessary. Examples of the acid include inorganic acids such as hydrochloric acid and sulfuric acid; organic acids such as acetic acid and methanesulfonic acid;
The reaction can be carried out in the presence of a base, if necessary. Examples of bases include alkali metal hydrides such as sodium hydride; alkali metal carbonates such as sodium carbonate, potassium carbonate and cesium carbonate; alkali metal hydroxides such as lithium hydroxide, sodium hydroxide and potassium hydroxide Such as
The reaction can be carried out in the presence of a solvent, if necessary. As the solvent, for example, aliphatic halogenated hydrocarbons such as dichloromethane and chloroform; aromatic hydrocarbons such as toluene and xylene; aprotic polar solvents such as acetonitrile, N, N-dimethylformamide, and dimethyl sulfoxide 1 type or 2 types or more can be suitably selected from water;
The reaction temperature is usually in the range of -20 ° C to 200 ° C. The reaction time is usually a few minutes to 24 hours.

Intermediate manufacturing method [3]
The compound of the formula (II-c) wherein R ² is X in the above formula (II) is reacted with 3-amino-4-methylpyridine with an inorganic nitrite or nitrite to form a diazonium salt, It can be produced by the Sandmeyer reaction in which a halogenating agent is reacted.

[Wherein, X is a halogen atom]
Examples of the inorganic nitrite and the nitrite include the same as the above-mentioned production method [3].
Examples of the halogenating agent include halogens such as chlorine, bromine and iodine; hydrohalic acids such as hydrochloric acid, hydrobromic acid and hydroiodic acid; copper (I) chloride, copper (I) bromide, copper iodide Copper (I) halides such as (I); Copper (II) halides such as copper (II) chloride and copper (II) bromide; and tetrafluoroboric acid.
The reaction can be carried out in the presence of a copper catalyst, if necessary. Examples of the copper catalyst include the above-mentioned copper (I) halides, copper (II) halides, copper (I) oxide, copper (II) sulfate pentahydrate and the like.
The reaction can be carried out in the presence of an acid, if necessary. Examples of the acid include inorganic acids such as hydrohalic acid and sulfuric acid mentioned above; organic acids such as acetic acid, methanesulfonic acid and p-toluenesulfonic acid; and the like.
The reaction can be carried out in the presence of a solvent, if necessary. As a solvent, the thing similar to the said manufacturing method [5] is mentioned, 1 type (s) or 2 or more types of these can be selected suitably, can be mixed and used.
The reaction temperature is usually in the range of -20 ° C to 200 ° C. The reaction time is usually a few minutes to 24 hours.

  As the compound of the formula (III), known compounds or commercially available compounds can be used.

  The desirable aspect of the pest control agent containing this invention compound is described below. The pest control agent containing the compound of the present invention is, for example, a control agent for pests, mites, nematodes or soil pests that cause problems in the field of agriculture and horticulture, that is, insecticides, acaricides, nematocides or soil pests Useful as. In addition, it is useful as a control agent of animal parasites, that is, as an animal repellent agent.

  The compounds of the present invention are useful as insecticides, acaricides, nematocides or soil pests, and more specifically, aphids such as green peach aphid, cotton aphid etc .; , Codling moth, ballworm, tobacco budworm, moth moth, kobunomaiga, kanokokokumonhamaki, Colorado potato beetle, urihamamushi, bowl weevil, ground beetles, leafhoppers, scale insects, stink bugs, whiteflys, thrips, locusts, bumblebees Agricultural pests such as starfishes, scarab beetles, crayfish, ants and the like; Gastropoda such as slugs and snails etc. Hygienic pests such as house dust mites, cockroaches, house fly and house mosquitoes etc; Storage damage such as oyster mushrooms, trash beetles etc Garbage such as moths, scarab beetles, termites etc., house pests, etc. pests such as house spider pests, spider spider mites, spider spider mites, spider spider mites, kanzawa spider mite, red spider mite, apple spider mite, brown spider mite, spider spider mite, spider mites etc. House dust mites such as Psyllium dominica, D. melanogaster tick, etc .; Phytoparasitoids such as mite, nematode nematode, cyst nematode, nematode nematode, negusa nematode, rice nematode nematode, strawberry nematode, etc. It is effective in the control of soil pests such as nematodes such as nematodes; Insecticides, acaricides, nematocides or soil pests containing the compound of the present invention are particularly effective for controlling plant parasitic mites, agricultural pests, plant parasitic nematodes and the like. Among them, they are very useful as insecticides or acaricides because they show superior effects in controlling plant parasitic mites and agricultural pests. In addition, insecticides, acaricides, nematocides or soil pests containing the compound of the present invention can be used for various resistant pests against drugs such as organic phosphorus agents, carbamate agents, synthetic pyrethroid agents, neonicotinoid agents and the like. It is also effective for control. Furthermore, since the compound of the present invention has excellent penetration and transferability, it is harmful to the soil by treating the soil containing the compound of the present invention with an insecticide, acaricide, nematocide or insecticidal agent against soil. At the same time as controlling insects, mites, nematodes, gastropods and isopods, it is also possible to control pests of the stem and leaf parts.

  As another desirable embodiment of the insecticide, the acaricide, the nematocide or the soil repellent containing the compound of the present invention, the above-mentioned plant parasitic mites, agricultural pests, plant parasitic nematodes, gastropods And insecticides, insecticides, nematocides or insecticides for controlling soil pests comprehensively.

  The insecticide, acaricide, nematocide or soil repellent containing the compound of the present invention is usually prepared by mixing the compound with various agricultural adjuvants, dust, granules, water dispersible granules, The present invention can be used by being formulated in various forms such as wettable powders, aqueous suspensions, oily suspensions, granular aqueous solvents, aqueous solvents, emulsions, solutions, pastes, aerosols, microsprays, etc. As long as it is compatible with the purpose of (1), it can be in any conventional formulation used in the art. Adjuvants used in the preparation include solid supports such as diatomaceous earth, calcium hydroxide, calcium carbonate, talc, white carbon, kaolin, bentonite, kaolinite, sericite, clay, sodium carbonate, sodium bicarbonate, sodium sulfate, zeolite, starch and the like; water , Toluene, xylene, solvent naphtha, dioxane, acetone, isophorone, methyl isobutyl ketone, chlorobenzene, cyclohexane, dimethyl sulfoxide, N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, alcohol and the like Solvents; fatty acid salts, benzoates, alkyl sulfosuccinates, dialkyl sulfosuccinates, polycarboxylates, alkyl sulfates, alkyl sulfates, alkyl aryl sulfates, alkyl diglycol ether sulfates, alcohols Sulfates, alkyl sulfonates, alkyl aryl sulfonates, aryl sulfonates, lignin sulfonates, alkyl diphenyl ether disulfonates, polystyrene sulfonates, alkyl phosphates, alkyl aryl phosphates, styryl aryls Phosphate salt, polyoxyethylene alkyl ether sulfate ester salt, polyoxyethylene alkyl aryl ether sulfate salt, polyoxyethylene alkyl aryl ether sulfate ester salt, polyoxyethylene alkyl ether phosphate, polyoxyethylene alkyl aryl phosphate ester salt , Anionic surfactants such as naphthalene sulfonate formaldehyde condensate; sorbitan fatty acid ester, glycerin fatty acid ester, fatty acid polyglyceride, fat Fatty acid alcohol polyglycol ether, acetylene glycol, acetylene alcohol, oxyalkylene block polymer, polyoxyethylene alkyl ether, polyoxyethylene alkyl aryl ether, polyoxyethylene styryl aryl ether, polyoxyethylene glycol alkyl ether, polyethylene glycol, polyoxy acid Nonionic surfactants such as ethylene fatty acid ester, polyoxyethylene sorbitan fatty acid ester, polyoxyethylene glycerin fatty acid ester, polyoxyethylene hydrogenated castor oil, polyoxypropylene fatty acid ester; olive oil, kapok oil, castor oil, sesame oil , Soy sauce, coconut oil, sesame oil, corn oil, rice bran oil, peanut oil, cottonseed oil, soybean oil, rapeseed oil, linseed oil, Riabura, vegetable oils and mineral oils such as liquid paraffin; and the like. Each component of these adjuvants can be used by appropriately selecting one or two or more without departing from the object of the present invention. Moreover, it can also be used suitably selected from what is known in the said field besides the above-mentioned adjuvant, for example, an extender, a thickener, an antisettling agent, an antifreezing agent, a dispersion stabilizer, drug damage reduction. Various adjuvants commonly used such as agents, fungicides, etc. can also be used. The compounding ratio (weight ratio) of this invention compound and various adjuvants is 0.001: 99.999-95: 5, Preferably it is 0.005: 99.995-90: 10. When actually using these preparations, use them as they are or dilute them to a predetermined concentration with a diluent such as water, and add various spreading agents (surfactant, vegetable oil, mineral oil, etc.) as necessary. It can be used.

  The application of the insecticide, acaricide, nematocide or soil repellent containing the compound of the present invention is generally made according to the difference in weather conditions, formulation form, application time, application site, kind and occurrence of diseases and pests, etc. Although it can not be specified, the concentration of the active ingredient is generally 0.05 to 800,000 ppm, preferably 0.5 to 500,000 ppm, and the application rate per unit area is 0.05 to 50,000 g, preferably 1 to 30,000 g of the present compound per hectare. It is. The present invention also includes a method of controlling pests, mites, nematodes or soil pests by such application methods, in particular, a method of controlling plant parasitic mites, agricultural pests and plant parasitic nematodes.

  The application of the various formulations of insecticides, acaricides, nematocides or soil pests containing compounds of the present invention, or dilutions thereof, is usually carried out by generally used application methods, that is, spraying (for example, Spraying, misting, atomizing, sprinkling, water surface application, etc.), soil application (mixing, irrigation, etc.), surface application (application, dressing, coating, etc.), immersion poisoning, etc. can be used. Moreover, it is also possible to mix and feed the above-mentioned active ingredient to feed to livestock so as to inhibit the generation and growth of harmful insects, particularly harmful insects, in the excrement. It can also be applied by the so-called ultra low volume application method. In this way it is possible to contain 100% of the active ingredient.

  The insecticide, acaricide, nematocide or soil repellent containing the compound of the present invention can be used together or in combination with other pesticides, fertilizers, safeners, etc. It may show excellent effects and effects. Other pesticides include herbicides, insecticides, acaricides, nematocides, soil pests, fungicides, antiviral agents, attractants, antibiotics, plant hormones, plant growth regulators, etc. Be In particular, an insecticidal composition, acaricidal composition, a nematode composition, or a composition for soil destructive insect pests, wherein the compound of the present invention and one or more of the active ingredient compounds of the other agricultural chemicals are used together or in combination. It is possible to improve the application range, time of drug treatment, control activity, etc. in a preferable direction. The compounds of the present invention and the active ingredient compounds of other agrochemicals may be separately formulated and mixed at the time of spraying, or both may be formulated and used together. The present invention also includes such insecticidal compositions, acaricidal compositions, nematode compositions or soil-killing pest compositions.

Examples of the active ingredient compound of an insecticide, acaricide, nematocide or soil pest agent (general name; including some under application, or Japan Plant Protection Association Test Code) among the above other pesticides are, for example, Profenofos (profenofos), dichlorvos, fenamiphos, fenitrothion, EPN, diazinon, chlorpyrifos (chlorpyrifos), chlorpyrifos-methyl, acephate, prothiophos Fosthiazate, cadusafos, disulfoton (dislufoton), isoxathion, isofenphos (isofenphos), ethion, ethion phos (etrimfos), quinalphos (quinalphos), dimethylvinphos (dimethylvinphos) ), Sulprofos (thioprofos), thiometh (thiometon), vamidothion, pyraclofos, pyridaphenthion, pyrimiphos-methyl, propaphos, phosalone, phosalone, formothion, malathion, malathion, tetrachlorvinphos (tetrachlorovinphos), chlorfenvinphos (chlorofenvinphos), cyanophos (cyanophos), trichlorfon (tricholfon), methidathion (methidathion), phentoate (phenthoate), ESP, azinphos-methyl (azinphos-methyl), phenthion (fenthion), heptenophos (heptenophos) Methoxychlor (methoxychlor), parathion (parathion), phosphocarb (phosphocarb), demeton-S-methyl (demeton-S-methyl), monocrotophos (monocrotophos), methamidophos (methamidophos), imiciaphos (imicyafos), parathion-methyl (parathion) -methyl), terbuphos ( organophosphate compounds such as terbufos), phosphamidon, phosmet (phosmet), phorate (phorate), phoxim (phoxim), triazophos (triazophos);
Carbaryl (proparyl), propoxur, aldicarb (aldicarb), carbofuran (carbofuran), thiodicarb (thiodicarb), methomil (methomyl), oxamyl (oxamyl), ethiophen carb (ethiofencarb), pyrimicarb (pirimicarb), fenobubub, Carbosulfan (carbosulfan), Benfuracarb (benfuracarb), Bendiocarb (bendiocarb), Furathiocarb (furathiocarb), Isoprocarb (isoprocarb), Metorcarb (metolcarb), xylylcarb (Xylco), Phenothiocarb (fenothiocarb) Compound;
Cartap (cartop), thiocyclam (thiocyclam), bensultap (bensultap), thiosultap sodium (thiosultap-sodium), thiosultap disodium (thiosultap-disium), monosultap (monosultap), bisultap (bisultap), hydrogen oxalate thiocyclam Nereistoxin derivatives such as (thiocyclam hydrogen oxalate);
Organochlorinated compounds such as dicofol, tetradiphone (tetradifon), endosulfan (endosulfan), dienochlor (dienochlor), dieldrin (dieldrin);
Organometallic compounds such as fenbutatin oxide and cyhexatin;
Fenvalerate (fenvalerate), permethrin (permethrin), cypermethrin (cypermethrin), deltamethrin (deltamethrin), cyhalothrin (cyhalothrin), tefluthrin (tefluthrin), etofenprox (ethofenprox), flufenprox (flufenprox), cyfluthrin (cyfluthrin) , Fenpropathrin, flucythrinate, fluvalinate, cycloprothrin, lambda-cyhalothrin, pyrethrins, esfenvalerate, Tetramethrin (tetramethrin), resmethrin (resmethrin), protrifenbute (protrifenbute), bifenthrin (bifenthrin), zeta-cypermethrin (zeta-cypermethrin), acritanthrin (acrinathrin), alpha-cypermethrin (alpha-cypermeline) (thrin), allethrin (allethrin), gamma cyhalothrin (gamma-cyhalothrin), theta-cypermethrin (theta-cypermethrin), taufluvalinate (tau-fluvalinate), tralomethrin (tralomethrin), profluthrin (profluthrin), beta cypermethrin ( Pyrethroid-based compounds such as beta-cypermethrin), beta-cyfluthrin (beta-cyfluthrin), methofluthrin (metofluthrin), phenothrin (phenothrin), flumethrin (flumethrin), decamethrin (decamethrin);
Diflubenzuron (diflubenzuron), chlorfluazuron (chlorfluazuron), teflubenzuron (teflubenzuron), flufenoxuron (flufenoxuron), triflumuron (triflumuron), hexaflumuron (hexaflumuron), lufenuron (lufenuron), nobarron (novaluron) noviflumuron (noviflumuron) Benzoylurea compounds such as bistrifluron, fluazuron);
Juvenile hormone-like compounds such as methoprene, pyriproxyfen, fenoxycarb, diofenolan;
Pyridazinone compounds such as pyridaben (pyridaben);
Pyrazole compounds such as fenpyroximate (fenpyroximate), fipronil (fipronil), tebufenpyrad (tebufenpyrad), ethiprole (ethiprole), tolfenpyrado (tolfenpyrad), acetoprole (acetoprole), pyrafluprole (pyrafluprole), pyriprole (pyriprole);
Imidacloprid (imidacloprid), nitenpyram (nitenpyram), acetamiprid (acetamiprid), thiacloprid (thiacloprid), thiamethoxam, clothianidin (clothianidin), nidinotefuran (nidinotefuran), dinotefurane Vonoid compounds;
Hydrazine compounds such as tebufenozide, methoxyfenozide, chromafenozide, halofenozide;
Pyridine compounds such as pyridalyl, flonicamid;
Cyclic keto enol compounds such as spirodiclofen, spiromesifen, spirotetramat;
Strobilurin-based compounds such as fluacrypyrim;
Pyridinamine-based compounds such as flufenerim;
Dinitro compounds, organic sulfur compounds, urea compounds, triazine compounds, hydrazone compounds, and as other compounds, flomethoquin, buprofezin, hexythiazox, amitraz, chlordimeform ), Silafluofen (silafluofen), triazamate (triazamate), pimetrozidine (pymetrozine), pyrididiphen (pyrimidifen), chlorfenapyr (chlorfenapyr), indoxacarb (indoxacarb), acequinocyl (acequinocyl), etoxazole (etoxazole), ciromazine (cyromazine) , 3-Dichloropropene (1,3-dichloropropene), diafenthiuron (diafenthiuron), benclothiaz (benclothiaz), bifenazate (bifenazate), propargite (propargite), clofenthezin (cl ofentezine), metaflumizone (metaflumizone), flubendiamide (flubendiamide), ciflumethophene (cyflumetofen), chlorantraniliprole (chlorantraniliprole), cyantraniliprol (cyantraniliprole), cyclaniliprol (cycliciliprole), cienopyraniphene (Pyrifluquinazon), phenazaquin (fenazaquin), amidoflumet (amidoflumet), sulfilamide (sulfluramid), hydramethylnon (hydramethylnon), meta aldehyde (metaldehyde), ryanodine (ryanodine), berbutin (verbutin), chlorobenzoate (chlorobenzoate), thia Zorylcinanonitrile (thiazolylcinnanonitrile), sulfoxaflor (sulfoxaflor), fluenesulfone (fluensulfone), triflumezopyrim (triflumezopyrim), afidopyropene, full Such as flupyradifuron, tetraniriprole (tetraniliprole), fluralaner (flulalaner), broflanilide, dicloromezotiaz, fluhexafon, tioxazafen (tioxazafen), DKN-2601, MSI-1302, NA-89, MIE-1209, ZDI-2502 Compound; and the like. Furthermore, crystal protein toxins produced by Bacillus thuringiensis such as Bacillus thuringiensis aizawai, Bacillus thuringiensis kurstaki, Bacillus thuringiensis israelensis, Bacillus thuringiensis japonensis, Bacillus thuringiensis tenebrionis, etc., an insect pathogenic virus agent, an insect pathogenic filamentous agent, a nematode pathogenic filamentous agent Microbial pesticides such as avermectin (avermectin), emamectin benzoate (emamectin Benzoate), milbemectin (milbemectin), milbemycin (milbemycin), spinosad (spinosad), ivermectin (ivermectin), lepimectin (lepimectin), DE-175, Antibiotics and semisynthetic antibiotics such as abamectin), emamectin, spinetoram; Natural products such as azadirachtin (azadirachtin), rotenone; Repellents such as deet Etc., mixed, combined It is also possible to.

Examples of the active ingredient compound of a fungicide among the above other pesticides (general name; including some under application, or Japan Plant Protection Association Test Code), for example, mepanipyrim (mepanipyrim), pyrimethanil (pyrimethanil), cyprodinil (cyprodinil) ), Anilino pyrimidine compounds such as ferimzone (ferimzone);
Tria like 5-chloro-7- (4-methylpiperidin-1-yl) -6- (2,4,6-trifluorophenyl) [1,2,4] triazolo [1,5-a] pyrimidine Zoropyrimidine compounds;
Pyridinamine compounds such as fluazinam;
Triadimefon (triadimefon), bitertanol (bitertanol), triflumizole (triflumizole), etaconazole (etaconazole), propiconazole (propiconazole), penconazole (penconazole), flusilazole (flusilazole), microbutanil (myclobutanil), cyproconazole cyproconazole), tebuconazole (tebuconazole), hexaconazole (hexaconazole), furconazole cis (furconazole-cis), prochloraz (prochloraz), metconazole (metconazole), epoxiconazole (epoxiconazole), tetraconazole (tetraconazole), Xpoconazole fumarate (oxpoconazole fumarate), sipconazole (sipconazole), prothioconazole (prothioconazole), triadimenol (triadimenol), flu tria fol (flutriafol), difenoconazole (difenoconazole) , Fluquinconazole (fluquinconazole), fenbuconazole (fenbuconazole), bromconazole (bromuconazole), diniconazole, diciconazole, tricyclazole (tricyclazole), probenazole (probenazole), simeconazole (simeconazole), peflazoate (pezulolate), ), Azole compounds such as imibenconazole (imibenconazole);
Quinoxaline compounds such as quinomethionates;
Dithiocarbamate compounds such as manneb (maneb), zineb (zineb), manzeb (mancozeb), polycarbamate, polycarbamate, methiram (metiram), propineb (propineb), thiram (thiram);
Organochlorine compounds such as phthalide, chlorothalonil, quintozene;
Imidazole compounds such as benomyl, cyazofamid, thiophanate-methyl, carbendazim, thiabendazole, fuberiazole;
Cyanoacetamide compounds such as cymoxanil;
Metalaxyl (metalaxyl), Metalaxyl-M (metalaxyl-M), Mefenoxam (mefenoxam), Oxadixyl (oxadixyl), ofurace (ofurace), Benalaxyl (benalaxyl), Benalaxyl-M (benalaxyl-M, aka kiralaxyl, chiralaxyl) ), Flalaxyl (furalaxyl), ciprofuram, carboxin, oxycarboxin, thifluzamide, thifluzamide, boscalid, bixachen (bixafen), isothianyl (isothianil), tiazinil (tiadinil)). Anilide compounds such as sedaxane;
Sulfamide compounds such as dichlofluanid;
Copper compounds such as cupric hydroxide, organic copper (oxine copper);
Isoxazole compounds such as hymexazol;
Fosetyl aluminum (fosetyl-Al), tolclophos methyl (tolclofos-methyl), S-benzyl O, O-diisopropyl phosphorothioate, O-ethyl S, S-diphenyl phosphorodithioate, aluminum ethyl hydrogen phosphonate, edifenphos, iprobenphos Organophosphorus compounds such as (iprobenfos);
Phthalimide compounds such as captan, captafol, folpet;
Dicarboximide compounds such as procymidone, iprodione, vinclozolin;
Benzanilide compounds such as flutolanil, mepronil;
3- (Difluoromethyl) -1-methyl-N-[(1RS, 4SR, 9RS) -1,2,3,4-tetrahydro-9-isopropyl-1,4-methanonaphthalen-5-yl ] Pyrazole-4-carboxamide and 3- (Difluoromethyl) -1-methyl-N-[(1RS, 4SR, 9SR) -1,2,3,4-tetrahydro-9-isopropyl-1,4-methanonaphthalene-5 -Yl] pyrazole-4-carboxamide mixtures (isopyrazam), silthiofam (silthiopham), amido compounds such as phenoxanyl (fenoxanil), furametopyr (furametpyr);
Benzamide compounds such as fluopyram, zoxamide;
Piperazine compounds such as triforine;
Pyridine compounds such as pyrifenox (pyrifenox);
Carbinol-based compounds such as fenarimol;
Piperidine compounds such as fenpropidin;
Morpholine compounds such as fenpropimorph and tridemorph;
Organotin compounds such as fentin hydroxide and fentin acetate;
Urea-based compounds such as pencycuron;
Cinnamic acid compounds such as dimethomorph, flumorph;
Phenylcarbamate compounds such as diethofencarb;
Cyanopyrrole compounds such as fludioxonil, fenpiclonil;
Azoxystrobin (azoxystrobin), Kresoxim-methyl (kresoxim-methyl), Metominostrobin (metominostrobin), Trifloxystrobin (trifloxystrobin), Picoxystrobin (picoxystrobin), Oryzastrobin (oryzastrobin), Dimoxystrobin ( strobilurin-based compounds such as dimoxystrobin), pyraclostrobin, fluoxastrobin;
Oxazolidinone compounds such as famoxadone;
Thiazolecarboxamide compounds such as ethaboxam;
Valinamide compounds such as iprovalicarb, benthiavalicar b-isopropyl;
Acylaminoacid compounds such as methyl N- (isopropoxycarbonyl) -L-valyl- (3RS) -3- (4-chlorophenyl) -β-alaninate (valiphenalate);
Imidazolinone-based compounds such as fenamidone;
Hydroxyanilide-based compounds such as fenhexamid;
Benzene sulfonamide type compounds such as flusulfamide (flusulfamide);
Oxime ether compounds such as cyflufenamide;
Atraquinone compounds;
Crotonic acid compounds;
Antibiotics such as validamycin (validamycin), kasugamycin (kasugamycin), polyoxins (polyoxins);
Guanidine compounds such as iminoctadine, dodine;
Quinoline-based compounds such as 6-tertiary butyl-8-fluoro-2,3-dimethylquinolin-4-yl acetate (tebufloquin);
Thiazolidine systems such as (Z) -2- (2-fluoro-5- (trifluoromethyl) phenylthio) -2- (3- (2-methoxyphenyl) thiazolidin-2-ylidene) acetonitrile (flutianil) Compound;
Other compounds include pyribencarb, isoprothiolane, isoprothiolane, pyroquilon, diclomezine, quinoxyfen, propamocarb hydrochloride chlorpicrin, chloropicrin, dazometum (zidometm), Salt (metam-sodium), nicobifen (nicobifen), metrafenone (metrafenone), UBF-307, diclocymet (diclocymet), proquinazid (proquinazid), amisulbrom (amisulbrom; also known as amibromdol), 3- (2,3,4 -Trimethoxy-6-methylbenzoyl) -5-chloro-2-methoxy-4-methylpyridine, 4- (2,3,4-trimethoxy-6-methylbenzoyl) -2,5-dichloro-3-trifluoromethyl Pyridine, pyriophenone, isofetamid mandipropamide (Mandipropamid), fluopicolide, carpropamid (mpropyldinocap), N-[(3 ', 4'-dichloro-1,1-dimethyl) phenacyl] -3-trifluoromethyl-2 -Pyridinecarboxamide, N-[(3 ', 4'-dichloro-1,1-dimethyl) phenacyl] -3-methyl-2-thiophenecarboxamide, N-[(3', 4'-dichloro-1,1- Dimethyl) phenacyl] -1-methyl-3-trifluoromethyl-4-pyrazolecarboxamide, N-[[2'-methyl-4 '-(2-propyloxy) -1,1-dimethyl] phenacyl] -3- Trifluoromethyl-2-pyridinecarboxamide, N-[[2'-methyl-4 '-(2-propyloxy) -1,1-dimethyl] phenacyl] -3-methyl-2-thiophenecarboxamide, N-[[[ 2'-Methyl-4 '-(2-propyloxy) -1,1-dimethyl] phenacyl] -1-methyl-3-trifluoromethyl-4-pyrazolecarboxamide, N-[[4'-(2-propy] Ruoxy) -1,1-dimethyl] phenacyl] -3-trifluoromethyl-2-pyridinecarboxamide, N-[[4 '-(2-propyloxy) -1,1-dimethyl] phenacyl] -3-methyl- 2-thiophenecarboxamide, N-[[4 '-(2-propyloxy) -1,1-dimethyl] phenacyl] -1-methyl-3-trifluoromethyl-4-pyrazolecarboxamide, N-[[2'- Methyl-4 '-(2-pentyloxy) -1,1-dimethyl] phenacyl] -3-trifluoromethyl-2-pyridinecarboxamide, N-[[4'-(2-pentyloxy) -1,1-] [Dimethyl] phenacyl] -3-trifluoromethyl-2-pyridinecarboxamide, spiroxamine, fenpyrazamine, mandestrobin, ZF-9646, BCF-051, BCM-061, BCM-062, etc. It can be mentioned.

  In addition, as pesticides which can be used in combination or in combination with the compound of the present invention, for example, active ingredient compounds of herbicides as described in The Pesticide Manual (15th edition), particularly those of soil treatment type, etc. There is.

  Specifically, as the animal repellent parasites, harmful ectoparasites which infest the body surface (back, swallow, lower abdomen, inner crotch etc.) of the host animal, or the body (stomach, intestinal tract, etc.) of the host animal It is effective for the control of harmful endoparasites that infect the lung, heart, liver, blood vessels, subcutaneous tissue, lymph tissue, etc.), but is particularly effective for the control of ectoparasites.

  The ectoparasites include, for example, animal parasitic mites and fleas. These types are very many and it is difficult to list them all, so an example is given.

The animal parasitic mites, for example Boophilus microplus (Boophilus microplus), Rhipicephalus sanguineus (Rhipicephalus sanguineus), Haemaphysalis longicornis (Haemaphysalis longicornis), Haemaphysalis flava (Haemaphysalis flava), Adenophora chima tick (Haemaphysalis campanulata), Isukachimadani (Haemaphysalis concinna), Yamatochimadani (Haemaphysalis japonica), H. kitaokai (Haemaphysalis kitaokai), Iyasuchimadani (Haemaphysalis ias), Ixodes ovatus (Ixodes ovatus), I. nipponensis (Ixodes nipponensis), Schulze ticks (Ixodes persulcatus), Takasago testudinarium (Amblyomma testudinarium), Ootogechimadani (Haemaphysalis ticks such as Megaspinosa ), the amino acid spider mite ( Dermacentor reticulatus ), and the giant spider mite ( Dermacentor taiwanesis ); Wakamo ( Dermanyssus gallinae ); Shidani (Ornithonyssus sylviarum), Torisashidani, such as Southern tri sand mite (Ornithonyssus bursa); Nan iodine tsutsugamushi (Eutrombicula wichmanni), red mites (Leptotrombidium akamushi), L. pallidum (Leptotrombidium pallidum), Fuji chiggers (Leptotrombidium fuji), Tosa mites ( Leptotrombidium tosa), Europe Aki mites (Neotrombicula autumnalis), the United States chiggers (Eutrombicula alfreddugesi), chiggers, such as Miyagawa Tama chiggers (Helenicula miyagawai); Inutsumedani (Cheyletiella yasguri), rabbit Tsumedani (Cheyletiella parasitivorax), Nekotsumedani (Cheyletiella blakei) Rabbit ticks ( Psoroptes cuniculi ), cattle ticks ( Chorioptes bovis ), long- eared mite ( Otodectes cynotis ), bald mite ( Sar coptes scabiei ), scaly ticks such as Notoedres cati ( Notoedres cati ); and Acne mites such as Scutellaris mite ( Demodex canis ). Among them, the animal repellent agent containing the compound of the present invention is particularly effective for controlling ticks and the like.

Examples of animal parasitic fleas include, for example, ectoparasitic insular insects belonging to the order of the order Siphonaptera , more specifically fleas belonging to the family of the human flea ( Pulicidae ), the family of long-legged seafish ( Ceratephyllus ) and the like. The fleas belonging to the human flea family include, for example, dog flea ( Ctenocephalides canis ), cat flea ( Ctenocephalides felis ), human flea ( Pulex irritans ), chicken soft flea ( Echidnophaga gallinacea ), pyops flea ( Xenopsylla cheopis ), Leptopsylla segnis ), European spiny fleas ( Nosopsyllus fasciatus ), spiny fleas ( Monopsyllus anisus ); and the like. Among them, the acaricidal agent containing the compound of the present invention is effective for controlling fleas belonging to the human flea family, in particular, dog flea, cat flea and the like.

  Other ectoparasites include, for example, lice such as cattle lice, lice, sheep lice, bovine lice, head lice, lice like dogflies, blood-sucking dipteran pests such as bovine rubbish, deer lice . In addition, as endoparasites, for example, nematodes such as lungworms, venchus, nodular worms, gastroparasites, roundworms, filamentous worms, etc .; Schistosomiasis such as Schistosoma japonicum, polychaetes, monoschimatodes, polychaetes; Schistosoma japonicum of Japan, flukes such as liver fluke; Coccidiosis, Plasmodium falciparum, enterosporidis, toxoplasma, chestnut Protozoa like ptosporidium etc. are mentioned.

  Host animals include various companion animals, livestock, poultry, etc. More specifically, dogs, cats, mice, rats, hamsters, guinea pigs, squirrels, rabbits, ferrets, birds (eg, pigeons, parrots, etc.) Examples include a nomen bird, a bird, a parrot, a calf, a canary), a cow, a horse, a pig, a sheep, a duck, a chicken, and the like. Among others, the acaricidal agent containing the compound of the present invention is effective for controlling pests or ticks ectoparasitizing a companion animal or livestock. Among pets or livestock, it is particularly effective for dogs, cats, cattle or horses.

  When the compound of the present invention is used as an animal repellent, it may be used as it is, and it may be used together with a suitable auxiliary agent, powder, granule, tablet, powder, capsule, liquid, emulsion, aqueous suspension, It can also be formulated and used in various forms such as an oily suspension. In addition, as long as it meets the purpose of the present invention, it can be in the form of any formulation used in the ordinary field other than the above-mentioned formulation form. As an adjuvant used for a formulation, the anionic surfactant and nonionic surfactant which were illustrated as an adjuvant for the formulation of the above-mentioned insecticide, acaricide, a nematocide, or a soil-repellent pest agent are mentioned. Cationic surfactants such as cetyltrimethylammonium bromide; water, acetone, acetonitrile, N-methylacetamide, N, N-dimethylacetamide, N, N-dimethylformamide, 2-pyrrolidone, N-methyl-2 -Pyrrolidone, kerosene, triacetin, methanol, ethanol, isopropanol, benzyl alcohol, ethylene glycol, propylene glycol, polyethylene glycol, liquid polyoxyethylene glycol, butyl diglycol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene Solvents such as recall monoethyl ether, diethylene glycol normal butyl ether, dipropylene glycol monomethyl ether, dipropylene glycol normal butyl ether; butyl hydroxyanisole, butyl hydroxy toluene, ascorbic acid, sodium metabisulfite, propyl gallate, sodium thiosulfate Such antioxidants; film forming agents such as polyvinyl pyrrolidone, polyvinyl alcohol, copolymers of vinyl acetate and vinyl pyrrolidone; as auxiliaries for the formulation of the above mentioned insecticides, acaricides, nematocides or soil repellents Vegetable oil and mineral oil exemplified; lactose, sucrose, glucose, starch, oat flour, corn flour, soybean meal, defatted rice bran, calcium carbonate, carriers such as other commercially available feed materials, and the like. Each component of these adjuvants can be used by appropriately selecting one or two or more without departing from the object of the present invention. Moreover, it can also be used suitably selected from what was known in the said field besides the above-mentioned adjuvant, and also can be used suitably selected from the various adjuvant etc. which are used in the above-mentioned agriculture and horticulture field. You can also

  The compounding ratio (weight ratio) of this invention compound and various adjuvants is about 0.1: 99.9-90: 10 normally. When actually using these preparations, use them as they are or dilute them to a predetermined concentration with a diluent such as water, and add various spreading agents (surfactant, vegetable oil, mineral oil, etc.) as necessary. It can be used.

  Administration of the compound of the present invention to a host animal is carried out orally or parenterally. Examples of the oral administration method include a method of administering a tablet, a liquid agent, a capsule, a wafer, a biscuit, a minced meat, other feed and the like containing the compound of the present invention. As a parenteral administration method, for example, a method of incorporating the compound of the present invention into a suitable formulation and then incorporating it into the body by intravenous injection, intramuscular administration, intradermal administration, subcutaneous administration and the like; spot-on Method of administering to the body surface by treatment, pour-on treatment, spray treatment, etc .; a method of embedding a resin piece or the like containing the compound of the present invention subcutaneously in a host animal, etc. may be mentioned.

  The dose of the compound of the present invention to the host animal varies depending on the method of administration, purpose of administration, disease condition etc., but usually it is a ratio of 0.01 mg to 100 g, preferably 0.1 mg to 10 g per kg of host animal weight. Administration is appropriate.

  The present invention also includes a method of controlling animal parasites by the administration method or dose as described above, in particular, a method of controlling ectoparasites or endoparasites.

  Further, in the present invention, various harmful diseases of the host animal caused by them may be prevented or treated by controlling harmful animal parasites as described above. Thus, the present invention also includes a preventive or therapeutic agent for parasite-induced animal disease containing the compound of the present invention as an active ingredient, and a method for preventing or treating parasite-induced animal disease.

  When the compound of the present invention is used as an animal repellent agent, various vitamins, minerals, amino acids, nutrients, enzyme preparations, antipyretics, sedatives, anti-inflammatory agents, bactericides, coloring agents, fragrances, as well as adjuvants It can be used in combination or in combination with preservatives and the like. In addition, it may be used together with or in combination with other various animal medicines and pesticides such as anthelmintic agents, anticoccidial agents, insecticides, acaricides, flanculants, nematocides, bactericides, antibacterial agents, etc. In this case, it may show a better effect. The present invention includes compositions for controlling animal parasites in which various components as described above are used in combination or in combination, and a method for controlling animal parasites using the same, in particular for controlling ectoparasites or endoparasites Methods are also included.

Next, some of the desirable embodiments of the substituted pyridine compound or a salt thereof of the present invention are illustrated, but these are not intended to limit the present invention.
(1) A substituted pyridine compound or a salt thereof represented by the above formula (I).
(2) R ¹ is a halogen atom, cyano, nitro, alkyl, alkenyl, alkynyl, haloalkyl, alkoxy, alkylthio, dialkylamino, alkylcarbonyl or alkoxycarbonyl; R ² is a halogen atom, cyano, nitro, alkenyl, alkynyl Or the compound according to (1) which is cycloalkyl, haloalkyl, alkoxy, alkenyloxy, alkynyloxy, alkylthio, alkenylthio, alkynylthio, alkylamino, dialkylamino, alkylsulfinyl, alkylsulfonyl, alkylcarbonyl or alkoxycarbonyl salt.
(3) R ¹ is alkyl, R ² is a halogen atom, alkoxy or nitro, L is -CHBrCHBr-, -CHCHClCH-, -CH = CH-, -CH = CCl- or -CH = CBr- The compound or its salt as described in a certain (1).
(4) The compound or a salt thereof according to (3), wherein R ¹ is tertiary butyl and R ² is a bromine atom, ethoxy or nitro.

  EXAMPLES The present invention will next be described by way of examples, which should not be construed as limiting the invention thereto. First, synthesis examples of the compound of the present invention will be described.

Synthesis example 1
Synthesis of (E) -4- (4- (t-butyl) styryl) -3-ethoxypyridine (Compound No. I-345-E)

  To 400 mg (2.92 mmol) of 3-ethoxy-4-methylpyridine, 568 mg (3.50 mmol) of 4-t-butylbenzaldehyde and 4 ml of acetic anhydride were added and the mixture was heated under reflux for 24 hours. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure to remove acetic anhydride. To the residue were added water and ethyl acetate, and the mixture was neutralized with aqueous sodium hydrogen carbonate solution and extracted. The aqueous layer was further extracted with ethyl acetate, the organic layers were combined, washed with saturated brine and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue is purified by silica gel column chromatography eluting with ethyl acetate / n-heptane = 5/1 to 2/1 to give (E) -4- (4- (t-butyl) styryl)- 216 mg of 3-ethoxypyridine (Compound No. I-345-E) were obtained as a brown solid.

Synthesis example 2
Synthesis of 4- (1,2-Dibromo-2- (4- (t-butyl) phenyl) ethyl) -3-ethoxypyridine (Compound No. I-45)

  A solution of 320 mg (1.14 mmol) of (E) -4- (4- (t-butyl) styryl) -3-ethoxypyridine (Compound No. I-345-E) in 5 ml of chloroform was cooled to 0 ° C. After dropwise addition of a chloroform solution (5 ml) of 272 mg (1.71 mmol) of bromine, the mixture was stirred at 0 ° C. for 15 minutes and at room temperature for 17 hours. Aqueous sodium thiosulfate solution and water were added, and the organic layer was separated. The aqueous layer was further extracted with ethyl acetate and washed with saturated brine. The organic layer was combined and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue is purified by silica gel column chromatography eluting with ethyl acetate / n-heptane = 3/1 to give 4- (1,2-dibromo-2- (4- (t-butyl) phenyl) 384 mg of ethyl) -3-ethoxypyridine (Compound No. I-45) was obtained as a pale yellow solid.

Synthesis example 3
Synthesis of (E) -4- (1-bromo-2- (4-t-butyl) phenyl) vinyl) -3-ethoxypyridine (Compound No. I-495-E)

  300 mg (0.68 mmol) of 4- (1,2-dibromo-2- (4- (t-butyl) phenyl) ethyl) -3-ethoxypyridine (Compound No. I-45), 113 mg of a 30% aqueous solution of sodium hydroxide 0.85 mmol) and 10 ml of isopropanol were added and the mixture was heated to reflux for 3 hours. The mixture was cooled to room temperature, water was added and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue is purified by silica gel column chromatography eluting with ethyl acetate / n-heptane = 5/1 to give (E) -4- (1-bromo-2- (4-t-butyl) phenyl ) Vinyl) 3-ethoxypyridine compound No. 1). 79 mg of I-495-E) were obtained as a pale yellow viscous oil.

Next, representative examples of the compounds of the formula (I) of the present invention are listed in Tables 1 and 2. These compounds can be synthesized based on the above synthesis examples or the various production methods described above. Although there may be geometric isomers derived from carbon double bonds for L in formula (I), the compounds in the table indicate mixtures in which they are included in any proportion. In the case of -CHBrCHBr-, -CHCHClCHCl-, -CHBrCHCl-, -CHClCHBr- for L, various stereoisomers derived from asymmetric carbon may exist, but the compounds in the table are in any proportions The mixture to be included is shown. The numerical values described in the physical property column of each table are the melting point (° C.), “Oil” indicates an oil, and the ¹ H-NMR spectrum data of compounds having no melting point are listed in Table 3. . In addition, No. in Table 1 shows a compound number. In the table, Me is methyl, Et is ethyl, n-Pr is normal propyl, i-Pr is isopropyl, n-Bu is normal butyl, i-Bu is isobutyl, s-Bu is secondary Butyl and t-Bu represent tertiary butyl.

  Among the compounds of the formula (I) listed in Table 1, compounds having a carbon double bond at L isolated as a single component instead of a mixture of geometric isomers are shown in Table 2.

Test Example 1 Effect Test on Tobilly Planthopper Rice seedlings were subjected to a soaking treatment in a chemical solution prepared so that the concentration of the compound of the present invention was 200 ppm. After the chemical solution was air dried, the roots were wrapped in moist absorbent cotton and placed in a test tube. Among them, about 10 2-3-year-old larvae were released, and the mouth of the tube was covered with gauze and left in a 25 ° C. lighted thermostatic chamber. The life and death of Tobiirounka were determined 5 days after the helminth, and the mortality (%) was determined by the following formula. As a result, the compound Nos. I-30, I-45, I-108, I-120, I-330-E, I-333-E, I-345-E, I-408-E, I-420. -E, I-420-Z and I-495-E showed a mortality of 90% or more.
Mortality rate (%) = (number of worms / number of worms) x 100

Test Example 2 Effect Test Against Tobacco Whitefly By means of a hand spray, a solution prepared to have a concentration of the compound of the present invention of 200 ppm was applied to a potted cucumber seedling infected with 1 to 2 instar larvae of B. tabaci. After the chemical solution was air dried, it was left in a 25 ° C. lighted temperature-controlled room. Ten days after the treatment, the number of aged larvae was investigated, and the control value was determined by the following formula. As a result, the compounds No. I-30, I-45, I-108, I-120, I-333-E, I-345-E, I-408-E, I-420-E, I-420. -Z and I-495-E showed a control value of 90 or more.
Control value = (1-(Ta x Cb) / (Tb x Ca)) x 100
Ta: Number of old-age larvae after treatment in treated cucumber seedlings
Tb: Number of 1 to 2 instar larvae before treatment in treated cucumber seedlings
Ca: Number of old-age larvae after treatment in untreated cucumber seedlings
Cb: Number of 1 to 2 instar larvae before treatment in untreated cucumber seedlings

Next, formulation examples are described.
Formulation example 1
(1) 20 parts by weight of the compound of the present invention (2) 70 parts by weight of clay

(3) White carbon 5 parts by weight (4) Sodium polycarboxylate 3 parts by weight (5) Sodium alkylnaphthalene sulfonate 2 parts by weight or more are uniformly mixed to obtain a wettable powder.

Formulation example 2
(1) The compound of the present invention 5 parts by weight (2) talc 60 parts by weight (3) calcium carbonate 34.5 parts by weight (4) liquid paraffin 0.5 parts by weight or more of them are uniformly mixed to obtain a dust.

Formulation example 3
(1) the compound of the present invention 20 parts by weight (2) N, N-dimethylacetamide 20 parts by weight (3) polyoxyethylene tristyryl phenyl ether 10 parts by weight (4) calcium dodecylbenzene sulfonate 2 parts by weight (5) xylene 48 Those in parts by weight or more are uniformly mixed and dissolved to obtain an emulsion.

Formulation example 4
(1) clay 68 parts by weight (2) sodium lignin sulfonate 2 parts by weight (3) polyoxyethylene alkyl aryl sulfate 5 parts by weight (4) white carbon 25 parts by weight or more of a mixture of each component and the compound of the present invention Mix at a weight ratio of 4: 1 to make a wettable powder.

Formulation example 5
(1) 50 parts by weight of the compound of the present invention (2) sodium alkylnaphthalene sulfonate formaldehyde condensate 2 parts by weight (3) silicone oil 0.2 parts by weight (4) 47.8 parts by weight or more of water uniformly mixed, Further, (5) 5 parts by weight of sodium polycarboxylate (6) 42.8 parts by weight of anhydrous sodium sulfate are added to the crushed stock solution, uniformly mixed, granulated and dried to obtain a water dispersible powder.

Formulation Example 6
(1) The compound of the present invention 5 parts by weight (2) polyoxyethylene octyl phenyl ether 1 part by weight (3) polyoxyethylene alkyl ether phosphate ester 0.1 part by weight (4) granular calcium carbonate 93.9 parts by weight (1 ) To (3) are uniformly mixed beforehand, diluted with an appropriate amount of acetone, and then sprayed to (4) to remove acetone to obtain granules.

Formulation example 7
(1) 2.5 parts by weight of the compound of the present invention (2) 2.5 parts by weight of N, N-dimethylacetamide (3) soybean oil 95.0 parts by weight Ultra low volume formulation).

Formulation Example 8
(1) 10 parts by weight of the compound of the present invention (2) 80 parts by weight of diethylene glycol monoethyl ether (3) Polyoxyethylene alkyl ether 10 parts by weight or more of components are uniformly mixed to obtain a solution.

Claims (7)

Formula (I):

[Wherein, R ¹ represents a halogen atom, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, alkoxy, alkenyloxy, alkynyloxy, cycloalkoxy, haloalkoxy, alkylthio, alkenylthio, alkynylthio, cycloalkylthio, Haloalkylthio, alkylamino, alkenylamino, alkynylamino, dialkylamino, dialkenylamino, dialkynylamino, alkylsulfinyl, alkenylsulfinyl, alkynylsulfinyl, cycloalkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, alkenylsulfonyl, alkynylsulfonyl, alkylcarbonyl , Alkoxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl , Alkylcarbonyloxy, alkylcarbonylamino or alkylcarbonylalkylamino;
R ² is a halogen atom, cyano, nitro, alkenyl, alkynyl, cycloalkyl, haloalkyl, hydroxy, alkoxy, haloalkoxy, alkenyloxy, alkynyloxy, cycloalkoxy, alkylthio, alkenylthio, alkynylthio, cycloalkylthio, alkylamino, alkenyl Amino, alkynylamino, dialkylamino, dialkenylamino, dialkynylamino, alkylsulfinyl, alkenylsulfinyl, alkynylsulfinyl, alkylsulfonyl, alkenylsulfonyl, alkynylsulfonyl, alkyloxyalkyl, alkylthioalkyl, alkylaminoalkyl, dialkylaminoalkyl, formyl , Alkylcarbonyl, alkoxycarbonyl, alkylaminocarbonyl , Dialkylaminocarbonyl, alkylcarbonyloxy, alkylcarbonylthio, alkylcarbonylamino or dialkylcarbonylamino;
L is a substituted pyridine compound or a salt thereof, represented by -CHBrCHBr-, -CHClCHCl-, -CHBrCHCl-, -CHClCHBr-, -CH = CH-, -CH = CCl- or -CH = CBr-. R ¹ is a halogen atom, cyano, nitro, alkyl, alkenyl, alkynyl, haloalkyl, alkoxy, alkylthio, dialkylamino, alkylcarbonyl or alkoxycarbonyl; R ² is a halogen atom, cyano, nitro, alkenyl, alkynyl, cycloalkyl, The compound or a salt thereof according to claim 1, which is haloalkyl, alkoxy, alkenyloxy, alkynyloxy, alkylthio, alkenylthio, alkynylthio, alkylamino, dialkylamino, alkylsulfinyl, alkylsulfonyl, alkylcarbonyl or alkoxycarbonyl. R ¹ is alkyl; R ² is a halogen atom, alkoxy or nitro; and L is -CHBrCHBr-, -CHClCHCl-, -CH = CH-, -CH = CCl- or -CH = CBr- Item 7. The compound according to item 1 or a salt thereof.   The pest control agent which contains the compound or its salt of Claim 1 as an active ingredient.   An insecticide, an acaricide, a nematocide or a soil insecticide containing the compound according to claim 1 or a salt thereof as an active ingredient.   An animal parasite control agent comprising the compound according to claim 1 or a salt thereof as an active ingredient.   A method for controlling pests by applying an effective amount of the compound according to claim 1 or a salt thereof.