JPH0725853A - Amido compound or its salt, its production and controller for harmful animal containing the same - Google Patents

Abstract

PURPOSE:To obtain a new amido compound useful as an active ingredient for a controller for harmful animals such as insecticide, acaricide, nematocide and agent for exterminating insect pests in soil by reacting a 4- trifluoromethylpyridine-3-carboxylic acid with a heterocyclic amine compound. CONSTITUTION:A 4-trifluoromethylpyridine-3-carboxylic acid or its reactive derivative is reacted with a heterocyclic amine compound of the formula HN(R)- A-X [A is alkanediyl; X is (substituted) heterocyclic group; R is H or alkyl; with the proviso that when R is H and A is methylene, X is nonsubstituted pyridine, nonsubstituted thienyl or nonsubstituted furyl] (e.g. 5-trifluoromethyl-2 pyridylmethylamine) in the presence of a base such as triethylamine at room temperature for 18 hours to give the objective amido compound of the formula useful as an active ingredient for a controller for harmful animals such as insecticide, acaricide, nematocide and agent for destroying insect pests in soil.

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an amide compound or a salt thereof, a process for producing them and a pest control agent containing them as an active ingredient.

[0002]

2. Description of the Related Art Various compounds are known as active ingredients of pest control agents. However, their chemical structure is different from the amide compounds of the present invention.

Conventionally, organic phosphorus compounds, carbamate compounds and pyrethroid compounds have been used as active ingredients of pest control agents such as insecticides, but as a result, some pests have recently acquired resistance to these insecticides. Came to do. Therefore, there is a need for a pest control agent that is effective against resistant pests. Furthermore, research and development of new pest control agents that are more effective against pests and are safer for fish, crustaceans, and livestock or have a broader spectrum are being conducted.

[0004]

SUMMARY OF THE INVENTION An object of the present invention is to provide an amide compound having a pest controlling action, a method for producing them and a pest controlling agent containing them.

[0005]

Means for Solving the Problems The present inventors have conducted extensive studies to develop a pest control agent, and have found that an amide compound having a specific chemical structure has an excellent pest control action. The present invention has been completed.

That is, the present invention has the general formula (I):

[0007]

[Chemical 4]

(Wherein A is an alkanediyl group and X is
Is an optionally substituted heterocyclic group, R is a hydrogen atom or an alkyl group, provided that when R is a hydrogen atom and A is a methylene group, X is an unsubstituted pyridyl, the same thienyl and the same furyl. Amide compound or salt thereof, a method for producing them, and a pest control agent containing them.

In the general formula (I), the alkanediyl group of A has a carbon number of 1 to 6, such as methylene group, ethylene group,
Examples thereof include a propylene group, a 1,1-ethanediyl group, a 1,1-propanediyl group, a 1,2-propanediyl group and a 2,2-propanediyl group.

In the general formula (I), the heterocyclic group of X is a 5-membered or 6-membered monocyclic or phenyl condensed ring system containing 1 to 3 heteroatoms selected from nitrogen atom, oxygen atom and sulfur atom. Examples of the group include a pyridyl group, a thienyl group, a furyl group, a pyrazinyl group, a 3-pyridazinonyl group, a thiazolyl group, an isoxazolyl group and a quinolyl group.

In the general formula (I), the substituent of the heterocycle represented by X is a halogen atom, C1-6 alkyl or haloC1-6.
Alkyl, C1-6 alkoxy, halo C1-6 alkoxy, C1-6 alkylthio, C3-8 cycloalkyl,
C3-8 cycloalkoxy, C1-6 alkoxycarbonyl, C1-6 alkylcarbonyl, C1-6 alkylcarbonyloxy, phenyl, phenoxy, phenylthio, amino, C1-6 alkyl substituted with 1 to 2 amino, cyano, nitro. , Hydroxy can be mentioned.

In the general formula (I), the alkyl group represented by R is one having 1 to 6 carbon atoms, such as a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, and a hexyl group. The compound may be a straight chain or branched chain structural isomer.

The compound of the general formula (I) may form a salt with an acidic substance or a basic substance, and as the salt with the acidic substance, a hydrochloride, hydrobromide, phosphate, sulfate, It may be an inorganic acid salt such as a nitrate, and the salt with a basic substance may be an inorganic or organic base salt such as a sodium salt, a potassium salt, a calcium salt, an ammonium salt or a dimethylamine salt.

The compound of general formula (I) or a salt thereof can be produced, for example, by the following method (A).

[0015]

[Chemical 5]

(Where A, X and R are as described above)

As the reactive derivative of 4-trifluoromethylpyridine-3-carboxylic acid represented by the formula (II),
It may be an acid halide, an ester or an acid anhydride.

The above reaction is usually carried out in the presence of a solvent and, if necessary, a base. Examples of the solvent include aromatic hydrocarbons such as benzene and toluene; ethers such as diethyl ether and tetrahydrofuran; hydrogenated hydrocarbons such as methylene chloride and chloroform; aprotic polar solvents such as acetonitrile, dimethylformamide and pyridine. included. These solvents may be used alone or as a mixture. Examples of the base include tertiary amines such as trimethylamine, triethylamine and pyridine; alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; alkali metal carbonates such as sodium carbonate and potassium carbonate; sodium methoxide and sodium ethoxy. Alkali metal alkoxides such as metal oxides are included. When the reactant is 4-trifluoromethylpyridine-3-carboxylic acid, a condensing agent such as dicyclohexylcarbodiimide, N, N′-carbonyldiimidazole, 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide, etc. Normally used.

The reaction temperature for the above reaction is usually from -50 ° C to +1.
The temperature is 00 ° C, preferably 0 to 30 ° C when the reactive derivative is an acid halide or an acid anhydride, and preferably 50 to 10 ° C when the reactive derivative is an ester.
It is 0 ° C. The reaction time is usually 0.1 to 24 hours.

The compound of the general formula (I) or a salt thereof may be produced, for example, by the following methods (B) to (D).

[0021]

[Chemical 6]

(Where A and X are as described above, and H
al is a halogen atom and R'is an alkyl group).

The above reactions (B) to (D) can be carried out in the same manner as the above reaction (A).

The compound of formula (II), 4-trifluoromethyl-3-pyridinecarboxylic acid, is a known compound and is commercially available. In addition, the reactive derivative can be obtained from the compound of formula (II).

The acid chloride is synthesized by using 4-trifluoromethylpyridine-3-carboxylic acid and a chlorinating agent such as thionyl chloride or phosphorus trichloride, if necessary, in catalytic amounts of N, N'-.
It is carried out by reacting at the reflux temperature in the presence of dimethylformamide.

The reactive derivative of the formula (II) other than 4-trifluoromethyl-3-pyridinecarbonyl chloride can be obtained by a method similar to the known method from benzoic acid to its reactive derivative. For example, acid bromide can be obtained by reacting 4-trifluoromethyl-3-pyridinecarboxylic acid with a brominating agent such as phosphorus tribromide, phosphorus oxybromide, and acetyl bromide. It can be obtained by reacting 4-trifluoromethyl-3-pyridinecarboxylic acid with its chloride or a desiccant, and the ester reacts 4-trifluoromethyl-3-pyridinecarboxylic acid with an alcohol. It can be obtained.

Further, 4-trifluoromethyl-3-pyridinecarboxylic acid can be obtained, for example, by the following method (E).

[0028]

[Chemical 7]

(Step 1) Step 1 is 2,6-dichloro-
4-trifluoromethylpyridine as lithium dialkylamide (preferably lithium diisopropylamide)
And in the presence of a solvent, by reacting with carbon dioxide in a gas or solid state.

Ethers such as tetrahydrofuran and diethyl ether are used as the solvent. The reaction temperature is generally -100 ° C to + 20 ° C, preferably -80 ° C to-
It is 20 ° C. and the reaction time is 1 to 12 hours.

(Step 2) Step 2 is carried out by reacting the 2,6-dichloro-4-trifluoromethyl-pyridine-3-carboxylic acid produced in Step 1 with a chlorinating agent in the presence of a solvent. .

Thionyl chloride and phosphorus pentachloride are used as the chlorinating agent, and aromatic hydrocarbons such as benzene and toluene are used as the solvent. The reaction temperature is usually 20-
The temperature is 120 ° C, preferably 50 to 100 ° C, and the reaction time is 1 to 6 hours.

(Step 3) Step 3 is the step 2
6-dichloro-4-trifluoromethyl-pyridine-3
Done by reacting the carboxylic acid chloride with an alcohol in the presence of a base.

Alcohols such as methanol and ethanol are used as alcohols, and tertiary bases such as triethylamine and pyridine are used as bases. The reaction temperature is generally 0 to 80 ° C, preferably 20 to 50 ° C, and the reaction time is 1 to 12 hours.

(Step 4) Step 4 is the step 2
6-dichloro-4-trifluoromethyl-pyridine-3
-Carboxylic acid ester and hydrogen are reacted in the presence of a solvent, a catalyst and a base.

Alcohols such as methanol and ethanol and ethers such as tetrahydrofuran are used as a solvent, palladium, palladium (II) chloride and the like are used as a catalyst, and a tertiary base such as triethylamine and pyridine is used as a base. , Sodium acetate, etc. are used. The reaction temperature is usually 0 to 100 ° C., preferably 2
It is 0 to 50 ° C., and the reaction time is 1 to 24 hours.

(Step 5) Step 5 is the step 4-
It is carried out by reacting trifluoromethylpyridine-3-carboxylic acid ester in the presence of a base and a solvent.

Examples of the solvent include water; alcohols such as methanol and ethanol, which may be used alone or in combination. As the base, an alkali metal hydroxide such as sodium hydroxide or potassium hydroxide is used. The reaction temperature is generally 0 to 100 ° C, preferably 20 to 80 ° C, and the reaction time is 1 to 12 hours.

The compound of formula (IV), that is, 4-trifluoromethylpyridine-3-carboxamide, can be obtained by reacting ammonia in place of the compound of formula (III) in the method of (A). . Also, 2,
It can also be obtained from 6-dichloro-3-cyano-4-trifluoromethylpyridine by the following method (F).

[0040]

[Chemical 8]

(Step 1) Step 1 is 2,6-dichloro-
It is carried out by reacting 3-cyano-4-trifluoromethylpyridine with concentrated sulfuric acid.

(Step 2) In Step 2, the 2,6-dichloro-4-trifluoromethyl-3-pyridinecarboxamide obtained in Step 1 is reacted with hydrogen in the presence of a solvent, a catalyst and a base. Has been done. As the solvent, for example, alcohols such as methanol and ethanol, and ethers such as tetrahydrofuran are used, as the catalyst, for example, palladium, palladium (II) chloride and the like are used, and as the base, for example, sodium acetate, sodium hydroxide, water and the like. Potassium oxide, triethylamine and the like are used.

The temperature of the reaction in step 2 is usually 0 ° C to 100 ° C.
C, reaction time is 1 to 24 hours.

The same applies when 2,6-dibromo-3-cyano-4-trifluoromethylpyridine is used in place of 2,6-dichloro-3-cyano-4-trifluoromethylpyridine in step 1 above. Can be carried out. This 2,6-dibromo-3-cyano-4-trifluoromethylpyridine reacts 3-cyano-2,6-dihydroxy-4-trifluoromethylpyridine with a brominating agent such as phosphorus oxybromide. It is obtained by

The compound of formula (VII) can be obtained by reacting R'NH ₂ in place of the compound of formula (III) in the above method (A). In addition, (B)
It can be obtained by reacting the compound of formula (VI) instead of the compound of formula (V) in the reaction of.

The compound of the present invention exhibits excellent activity as an active ingredient of pest control agents such as insecticides, acaricides, nematicides, and soil insecticides.

For example, phytoparasitic mites such as spider mites, spider mites, citrus mites, and acarids, aphids such as peach aphids, cotton aphids, diamondback moth, bollworms, common beetles, codling moths, ball worms, tobacco bad worms, mai maiga, and colorado Leaf beetle, cuticle beetle, bauweville, planthoppers, leafhoppers, scale insects, stink bugs, whitefly,
Thrips, grasshoppers, sand flies, scarabs,
Agricultural pests such as Tamanaaga, Kaburagaga, and ants, sanitary pests such as house dust mites, cockroaches, house flies, and Culex pipiens, Bakuga, Azuki bean weevils, Kokunusutomoki,
It is also effective against storage insecticides such as bedbugs, clothes such as burrs, scabbard beetles, termites, house pests, and fleas, lice and flies parasitic on livestock. It is also effective against plant-parasitic nematodes such as mosquitoes, cyst nematodes, mess nematodes, rice garlic nematodes, strawberry nematodes, and pine wood nematodes. Also,
It is also effective against soil pests. Examples of soil pests referred to here include gastropods such as slugs and snails, and isopods such as pill bugs and wallworms. Among them, the compound of the present invention exhibits an excellent effect on aphids such as green peach aphid and cotton aphid. Further, it is also effective against organic phosphorus agents such as aphids, carbamate agents, and synthetic pyrethroid-resistant pests. Furthermore, since the compound of the present invention has an excellent osmotic transfer property, it is possible to control soil harmful insects, mites, nematodes, gastropods, and isopods by treating the compound of the present invention in soil. At the same time, it is possible to control pests on foliage.

When the compound of the present invention is used as an active ingredient of a pest control agent, emulsions, suspensions, powders, granules, wettable powders, water, together with pesticide adjuvants are used as in the case of conventional pesticide formulations. It can be formulated in various forms such as a solvent, a liquid agent, a flowable agent, a wettable granule, an aerosol agent, a paste agent, and a trace amount spray agent. The compounding ratio of these is usually 0.1 to 90 parts by weight of the active ingredient and 10 to 99.9 parts by weight of the agricultural chemical adjuvant. In the actual use of these preparations, they can be used as they are or diluted with a diluent such as water to a predetermined concentration and used.

Examples of the agricultural chemicals auxiliary agent include carriers, emulsifiers, suspending agents, dispersing agents, spreading agents, penetrants, wetting agents, thickeners, stabilizers, etc., which may be appropriately added if necessary. Good. The carrier is divided into a solid carrier and a liquid carrier,
As the solid carrier, starch, activated carbon, soybean flour, wheat flour, wood flour, fish meal, powdered animal or plant powder such as milk powder, talc, kaolin, bentonite, calcium carbonate, zeolite, diatomaceous earth, white carbon, clay, mineral powder such as alumina. As the liquid carrier, water, alcohols such as isopropyl alcohol and ethylene glycol,
Ketones such as cyclohexanone and methyl ethyl ketone, ethers such as dioxane and tetrahydrofuran, aliphatic hydrocarbons such as kerosene and light oil, aromatic hydrocarbons such as xylene, trimethylbenzene, tetramethylbenzene, methylnaphthalene and solvent naphtha, chlorobenzene And halogenated hydrocarbons such as amide, acid amides such as dimethylacetamide, esters such as glycerin ester of fatty acid, nitriles such as acetonitrile, and sulfur-containing compounds such as dimethyl sulfoxide.

If necessary, other pesticides, such as insecticides, acaricides, nematicides, fungicides, antiviral agents, attractants, herbicides, plant growth regulators, etc., are mixed and used together. In this case, a more excellent effect may be exhibited.

Examples of the active ingredient compound of the above insecticide, acaricide or nematicide include, for example, O- (4-bromo-2).
-Chlorophenyl) O-ethyl S-propyl phosphorothioate (generic name: profenophos), O- (2,2-
Dichlorovinyl) O, O-dimethyl phosphate (generic name: dichlorvos), O-ethyl O- [3-methyl-4- (methylthio) phenyl] N-isopropyl phosphoramidate (generic name: fenamiphos), O, O −
Dimethyl O- (4-nitro-m-tolyl) phosphorothioate (generic name: fenitrothion), O-ethyl
O- (4-nitrophenyl) phenylphosphonothioate (generic name: EPN), O, O-diethyl O- (2-
Isopropyl-6-methylpyrimidin-4-yl) phosphorothioate (generic name: diazinon), O, O-dimethyl O- (3,5,6-trichloro-2-pyridyl) phosphorothioate (generic name: chlorpyrifosmethyl), O, S-dimethyl N-acetylphosphoramidothioate (generic name: acephate), O- (2,4-
Dichlorophenyl) O-ethyl S-propyl phosphorodithioate (generic name: prothiophos), (RS)-
S-sec-butyl O-ethyl 2-oxo-1,3-
Organic phosphate compounds such as thiazolidin-3-ylphosphonothioate (compounds described in US Pat. No. 4590182);

1-naphthyl N-methylcarbamate (generic name: carbaryl), 2-isopropoxyphenyl N-methylcarbamate (generic name: propoxur),
2-methyl-2- (methylthio) propionaldehyde O-methylcarbamoyl oxime (generic name: aldicarb), 2,3-dihydro-2,2-dimethylbenzofuran-7-yl N-methylcarbamate (generic name: carbofuran), Dimethyl N, N '-[thiobis {(methylimino) carbonyloxy}] bisethaneimidothioate (generic name: thiodicarb), S-methyl N-
(Methylcarbamoyloxy) thioacetimidate (generic name: Mesomel), N, N-dimethyl-2-methylcarbamoyloxyimino-2- (methylthio) acetamide (generic name: oxamyl), 2- (ethylthiomethyl) phenyl N-methyl carbamate (generic name: etiophencarb), 2-dimethylamino-5,6-dimethylpyrimidin-4-yl N, N-dimethylcarbamate (generic name: pyrimicarb), 2-sec-butylphenyl N-methylcarbamate ( Generic name: phenopcarb) and other carbamate compounds;

S, S'-2-dimethylaminotrimethylene bis (thiocarbamate) (generic name: cartap),
Nereistoxin derivatives such as N, N-dimethyl-1,2,3-trithian-5-ylamine (generic name: thiocyclam);

2,2,2-trichloro-1,1-bis (4-chlorophenyl) ethanol (generic name; dicofol), 4-chlorophenyl-2,4,5-trichlorophenylsulfone (generic name: tetradiphone), etc. Organic chlorine compounds;

Organometallic compounds such as bis [tris (2-methyl-2-phenylpropyl) tin] oxide (generic name: fenbutatin oxide);

(RS) -α-Cyano-3-phenoxybenzyl (RS) -2- (4-chlorophenyl) -3-methylbutyrate (generic name: fanvalerate), 3-phenoxybenzyl (1RS) -cis , Transformer-3-
(2,2-dichlorovinyl) -2,2-dimethylcyclopropanecarboxylate (generic name: permethrin),
(RS) -α-cyano-3-phenoxybenzyl (1R
S) -cis, trans-3- (2,2-dichlorovinyl) -2,2-dimethylcyclopropanecarboxylate (generic name: cypermethrin), (S) -α-cyano-
3-phenoxybenzyl (1R) -cis-3- (2,2
-Dibromovinyl) -2,2-dimethylcyclopropanecarboxylate (generic name: tertamethrin), (R
S) -α-Cyano-3-phenoxybenzyl (1RS)
-Cis, trans-3- (2-chloro-3,3,3-trifluoropropenyl) -2,2-dimethylcyclopropanecarboxylate (generic name: cyhalothrin), 4-
Methyl-2,3,5,6-tetrafluorobenzyl-3
-(2-chloro-3,3,3-trifluoro-1-propenyl) -2,2-dimethylcyclopropanecarboxylate (generic name: tefluthrin), 2- (4-ethoxyphenyl) -2-methylpropyl 3 -Pyrethroid compounds such as phenoxybenzyl ether (generic name: etofenprox);

1- (4-chlorophenyl) -3- (2,
6-difluorobenzoyl) urea (generic name: diflubenzuron), 1- [3,5-dichloro-4- (3-chloro-5-trifluoromethyl-2-pyridyloxy) phenyl] -3- (2,6- Difluorobenzoyl) urea (generic name: chlorfluazuron), 1- (3,5-dichloro-2,4-difluorophenyl) -3- (2,6
Benzoylurea-based compounds such as difluorobenzoyl) urea (generic name: teflubenzuron);

Juvenile hormone-like compounds such as isopropyl (2E, 4E) -11-methoxy-3,7,11-trimethyl-2,4-dotecadienoate (generic name: methoprene);

Pyridazinone compounds such as 2-t-butyl-5- (4-t-butylbenzylthio) -4-chloro-3 (2H) -pyridazinone (generic name: pyridaben);

T-Butyl 4-[(1,3-dimethyl-
5-phenoxypyrazol-4-yl) methyleneaminooxymethyl] benzoate (generic name: fenpyroximate), 5-amino-1- (2,6-dichloro-α,
α, α-trifluoro-p-toluyl) -4-trifluoromethylsulfinylpyrazole-3-carbonitrile (generic name; fipronil), N- (4-t-butylbenzyl) -4-chloro-3-ethyl- Pyrazole compounds such as 1-methylpyrazole-5-carboxamide (generic name; tebufenpyrad);

1- (6-chloro-3-pyridylmethyl)
-N-nitro-imidazolidine-2-ylideneamine (generic name: imidacloprid), 1- [N- (6-chloro-3-pyridylmethyl) -N-ethylamino] -1-
Methylamino-2-nitroethylene (generic name: nitenpyram), N ¹ -[(6-chloro-3-pyridyl) methyl] -N ² -cyano N ¹ -methylacetamidine (compound described in European Publication No. 456826). ) 1-
(6-chloro-3-pyridylmethyl) -2- (1-nitro-2-allylthioethylidene) imidazolidine (European publication No. 437784), 1- (6-chloro-
3-pyridylmethyl) -2- (1-nitro-2-ethylthioethylidene) imidazolidine (European publication N
O. 437784), 1- (6-chloro-3-pyridylmethyl) -2- (1-nitro-2-β-methylallylthioethylidene) imidazolidine (European publication NO.
Nitro compounds such as 437784);

N'-t-butyl-N'-3,5-dimethylbenzoyl-N-benzo [b] thiophene-2-carbohydrazide, N'-t-butyl-N'-3,5-dimethylbenzoyl- N-4,5,6,7-tetrahydrobenzo [b] thiophene-2-carbohydrazide, N'-
t-butyl-N'-3,5-dimethylbenzoyl-N-
5,6-dihydro-4H-cyclopenta [b] thiophene-2-carbohydrazide, N'-t-butyl-N'-
Hydrazine compounds such as 3 ', 5'-dimethylbenzoyl-N-4-ethylphenylcarbohydrazide (generic name: tebufenozide);

Dinitro compounds, organic sulfur compounds, urea compounds, triazine compounds, hydrazone compounds and 2-t-butylimino-3 as other compounds.
-Isopropyl-5-phenyl-3,4,5,6-tetrahydro-2H-1,3,5-thiadiazin-4-one (generic name: buprofezin), trans- (4-chlorophenyl) -N-cyclohexyl-4 -Methyl-2-oxothiazolidinone-3-carboxamide (generic name: hexithiazox), N-methylbis (2,4-xylyliminomethyl) amine (generic name: amitraz), N'-
(4-Chloro-o-tolyl) -N, N-dimethylformamidine (generic name: chlordimeform), (4-ethoxyphenyl)-[3- (4-fluoro-3-phenoxyphenyl) propyl] (dimethyl) silane (Generic name: silafluofene), ethyl (3-t-butyl-1-dimethylcarbamoyl-1H-1,2,4-triazol-5-ylthio) acetate (generic name: triazamate), 4,5-dihydro-6- Methyl-4- (3-pyridylmethyleneamino) -1,2,4-triazine-3
(2H) -one (generic name: pymetrozine), 5-chloro-N- [2- [4- (2-ethoxyethyl) -2,3-
Dimethylphenoxy] ethyl] -6-ethylpyrimidin-4-amine (generic name: pyrimidiphene), 4-bromo-2- (4-chlorophenyl) -1-ethoxymethyl-
Examples thereof include compounds such as 5-trifluoromethylpyrrole-3-carbonitrile (the compounds described in JP-A-1-104042). Further, they can be mixed and used in combination with microbial agents such as BT agents and insect pathogenic virus agents, and antibiotics such as avermectin and milbemainsi.

Examples of the active ingredient compound of the bactericide include pyrimidinamine compounds such as 2-anilino-4-methyl-6- (1-propynyl) pyrimidine (the compound described in Japanese Patent Laid-Open No. 63-208581). ;

1- (4-chlorophenoxy) -3,3-
Dimethyl-1- (1H-1,2,4-triazole-1
-Yl) butanone (generic name: triadimefon), 1-
(Biphenyl-4-yloxy) -3,3-dimethyl-
1- (1H, 1,2,4-triazol-1-yl) butan-2-ol (generic name: bitertanol), 1-
[N- (4-chloro-2-trifluoromethylphenyl) -2-propoxyacetimidoyl] imidazole (generic name: triflumizole), 1- [2- (2,4-
Dichlorophenyl) -4-ethyl-1,3-dioxolan-2-ylmethyl] -1H-1,2,4-triazole (generic name: etaconazole), 1- [2- (2,4-
Dichlorophenyl) -4-propyl-1,3-dioxolan-2-ylmethyl] -1H-1,2,4-triazole (generic name: propiconazole), 1- [2- (2,2
4-dichlorophenyl) pentyl] -1H-1,2,4
-Triazole (generic name: penconazole), bis (4
-Fluorophenyl) (methyl) (1H-1,2,4-
Triazol-1-ylmethyl) silane (generic name: flusilazole), 2- (4-chlorophenyl) -2- (1
H-1,2,4-triazol-1-ylmethyl) hexanenitrile (generic name: microbutanyl), (2R
S, 3RS) -2- (4-Chlorophenyl) -3-cyclopropyl-1- (1H-1,2,4-triazole-
1-yl) butan-2-ol (generic name: cyproconazole), (RS) -1- (4-chlorophenyl) -4,
4-Dimethyl-3- (1H-1,2,4-triazol-1-ylmethyl) pentan-3-ol (generic name: terpconazole), (RS) -2- (2,4-dichlorophenyl) -1 -(1H-1,2,4-triazole-
1-yl) hexan-2-ol (generic name: hexaconazole), (2RS, 5RS) -5- (2,4-dichlorophenyl) tetrahydro-5- (1H-1,2,4-
Triazol-1-ylmethyl) -2-furyl 2,2
2-trifluoroethyl ether (generic name: farconazole cis), N-propyl-N- [2- (2,4,6)
-Trichlorophenoxy) ethyl] imidazole-1-
Azole compounds such as carboxamide (generic name: prochloraz);

6-methyl-1,3-dithiolo [4,5-
b] a quinoxaline-based compound such as quinoxalin-2-one (generic name: quinomethionate);

Manganese ethylene bis (dithiocarbamate) polymer (generic name: Manneb), zinc ethylene bis (dithiocarbamate) polymer (generic name: Zineb), zinc (zinc) and manganese ethylene bis (dithiocarbamate) ) (Manneb) complex compound (generic name:
Dithiocarbamate compounds such as manzeb), dizinc bis (dimethyldithiocarbamate) ethylene bis (dithiocarbamate) (generic name: polycarbamate), zinc propylene bis (dithiocarbamate) (generic name: propineb);

Organochlorine compounds such as 4,5,6,7-tetrachlorophthalide (generic name: fthalide), tetrachloroisophthalonitrile (generic name: chlorothalonil), pentachloronitrobenzene (generic name: quintozene);

Methyl 1- (butylcarbamoyl) benzimidazol-2-ylcarbamate (generic name: benomyl), dimethyl 4,4 '-(o-phenylene) bis (3-thioallophanate) (generic name: thiophanate methyl), methyl Benzimidazole-based compounds such as benzimidazol-2-ylcarbamate (generic name: carbendazim);

3-chloro-N- (3-chloro-2,6-
Dinitro-4-α, α, α-trifluorotolyl) -5
A pyridinamine-based compound such as trifluoromethyl-2-pyridinamine (generic name: fluazinam);

A cyanoacetamide compound such as 1- (2-cyano-2-methoxyiminoacetyl) -3-ethylurea (generic name: Simoxanil);

Methyl N- (2-methoxyacetyl)-
N- (2,6-xylyl) -DL-alaninate (generic name: metalaxyl), 2-methoxy-N- (2-oxo-1,3-oxazolidin-3-yl) aceto-2 ',
6'-xylidide (generic name: oxadixyl), (±)
-Α-2-chloro-N- (2,6-xylylacetamide) -γ-butyrolactone (generic name: offlace), methyl N-phenylacetyl-N- (2,6-xylyl) -DL-alaninate ( (Generic name: benalaxyl),
Methyl N- (2-furoyl) -N- (2,6-xylyl) -DL-alaninate (generic name: furaraxyl),
(±) -α- [N- (3-chlorophenyl) cyclopropanecarboxamide] -γ-butyrolactone (generic name:
Phenylamide compounds such as cyprofuran);

N-dichlorofluoromethylthio-N ',
N'-dimethyl-N-phenylsulfamide (generic name:
Sulfenic acid compounds such as diclofluanid);

Cupric hydroxide (general name: cupric hydroxide),
Copper-based compounds such as copper 8-quinolinolate (generic name: organic copper);

Isoxazole compounds such as 5-methylisoxazol-3-ol (generic name: hydroxyisoxazole);

Aluminum tris (ethylphosphonate) (generic name: fosetylaluminum), O-2,6-
Dichloro-p-tolyl-O, O-dimethylphosphorothioate (generic name: tolclofos-methyl), S-benzyl O, O-diisopropylphosphorothioate, O-
Organophosphorus compounds such as ethyl S, S-diphenylphosphorodithioate and aluminum ethylhydrogenphosphonate;

N- (trichloromethylthio) cyclohex-4-ene-1,2-dicarboximide (general name: captan), N- (1,1,2,2-tetrachloroethylthio) cyclohex-4-ene-1 , 2-dicarboximide (generic name: captafol), N- (trichloromethylthio) phthalimide (generic name: folpet), and other N-halogenothioalkyl compounds;

N- (3,5-dichlorophenyl) -1,
2-Dimethylcyclopropane-1,2-dicarboximide (generic name: procymidone), 3- (3,5-dichlorophenyl) -N-isopropyl-2,4-dioxoimidazolidine-1-carboxamide (generic name: Iprodione), (RS) -3- (3,5-dichlorophenyl)-
5-methyl-5-vinyl-1,3-oxazolidine-
Dicarboximide-based compounds such as 2,4-dione (generic name: vinclozolin);

Benzanilide compounds such as α, α, α-trifluoro-3'-isopropoxy-o-toluanilide (general name: flutolanil) and 3'-isopropoxy-o-toluanilide (general name: mepronil);

2- (1,3-dimethylpyrazole-4-
Ilcarbonylamino) -4-methyl-3-pentenenitrile (compound described in British Patent No. 2190375), α- (nicotinylamino)-(3-fluorophenyl) acetonitrile (JP-A-63-135364).
Benzamide-based compounds such as the compounds described in 1.);

Piperazine compounds such as N, N '-[piperazine-1,4-diylbis [(trichloromethyl) methylene]] diformamide (generic name: triphorine);

Pyridine compounds such as 2 ', 4'-dichloro-2- (3-pyridyl) acetophenone O-methyloxime (generic name: pyriphenox);

(±) -2,4'-Dichloro-α- (pyrimidin-5-yl) benzhydryl alcohol (generic name: phenalimol), (±) -2,4'-difluoro-
Carbinol compounds such as α- (1H-1,2,4-triazol-1-ylmethyl) benzhydryl alcohol (generic name: flutriafol);

(RS) -1- [3- (4-tertiary-
A piperidine-based compound such as butylphenyl) -2-methylpropyl] piperidine (generic name: phenpropidin);

(±) -cis-4- [3- (4-tert-butylphenyl) -2-methylpropyl] -2,6
A morpholine compound such as dimethylmorpholine (generic name: fenpropimorph);

Triphenyltin hydroxide (generic name:
Fentin hydroxide), triphenyltin acetate (generic name: fentin acetate) and other organotin compounds;

Urea compounds such as 1- (4-chlorobenzyl) -1-cyclopentyl-3-phenylurea (generic name: Pensicurone);

A cinnamic acid compound such as (E, Z) 4- [3- (4-chlorophenyl) -3- (3,4-dimethoxyphenyl) acryloyl] morpholine (generic name: dimethomorph);

Phenylcarbamate compounds such as isopropyl 3,4-diethoxycarbanilate (generic name: dietofencalp);

3-Cyano-4- (2,2-difluoro-
Cyanopyrrole compounds such as 1,3-benzodioxol-4-yl) pyrrole (trade name: sapphire) and 3- (2 ', 3'-dichlorophenyl) -4-cyano-pyrrole (generic name: fenpiclonyl) ;

3-chloro-N- (3-chloro-2,6-
Dinitro-4-α, α, α-trifluorotolyl) -5
A pyridinamine-based compound such as trifluoromethyl-2-pyridinamine (generic name: fluazinam);

Atraquinone compounds; crotonic acid compounds; antibiotics and other compounds such as diisopropyl 1,3-dithiolane-2-ylidene-malonate (generic name: isoprothiolane), 5-methyl-1,2,4-
Triazolo [3,4-b] benzazole (generic name: tricyclazole), 1,2,5,6-tetrahydropyrrolo [3,2,1-ij] quinolin-4-one (generic name:
Pyroquinone), 6- (3,5-dichloro-4-methylphenyl) -3 (2H) -pyridazinone (generic name: dichromedin), 3-allyloxy-1,2-benzisothiazole-1,1-dioxide (general) Name: probenazole) and the like.

In addition, a suitable mixing weight ratio of the other agent used in combination with the compound of the present invention is generally 1: 300 to 300:
1, preferably 1: 100 to 100: 1.

Application of the pest control agent of the present invention is generally 0.1 to 500000 ppm, preferably 1 to 10000.
Perform at an active ingredient concentration of 0 ppm. The concentrations of these active ingredients can be appropriately changed depending on the form of the preparation, the method of application, the purpose, the time, the place, the state of occurrence of harmful insects and the like. For example, in the case of aquatic pests, it can be controlled even by spraying a drug solution having the above-mentioned concentration range to the place of occurrence, and therefore the active ingredient concentration range in water is below the above. Application rate per unit area is 1
About 0.1 to 5000 g as an active ingredient compound per ha
Preferably 10 to 1000 g are used. However, it is possible to deviate from these ranges in special cases.

Application of various preparations containing the compound of the present invention, or a dilution thereof, is generally carried out by application methods such as spraying (spraying, spraying, misting, atomizing, granulation, water surface application, etc.). ), Soil application (mixing, irrigation, etc.), surface application (application, dressing, coating, etc.),
It can be carried out using a soaking poison bait or the like. It is also possible to feed livestock by mixing the above-mentioned active ingredient with feed to control the development and growth of harmful insects, especially harmful insects, in the excrement. In addition, the so-called ultra-high concentration small amount spray method
It can also be applied by a low volume). In this way it is possible to contain 100% of the active ingredient.

Further, the application of the pesticidal composition of the present invention can be carried out not only when it is applied directly to a pest, but also when the amide compound of formula (I) or a salt thereof acts on a pest. Shall also be included. As such an example, another active ingredient compound is represented by the formula (I) in an environment such as soil.
In some cases, it may act on a pest after being decomposed into the amide compound.

[0097]

EXAMPLES Examples of the present invention will be described below, but the present invention is not limited to these examples.

Synthesis Example Synthesis of N-[(5-trifluoromethyl) -2-pyridylmethyl] -4-trifluoromethyl-3-pyridinecarboxamide (Compound No. 1)

(1) Synthesis of 5-trifluoromethyl-2-pyridylmethylamine 2-cyano-5-trifluoromethylpyridine 1.5 g
Solution of 15% ethanol in 10% palladium on carbon.
15 g was added, and the mixture was stirred under hydrogen pressure for 15 hours. After completion of the reaction, the reducing catalyst was removed with Celite, and the filtrate was concentrated to 5
-1.0 g of crude product of trifluoromethyl-2-pyridylmethylamine was obtained. This product was used in the next reaction without purification. (2) 4-trifluoromethyl-3-pyridinecarboxylic acid 0.40 g and thionyl chloride 0.50 g benzene 10
3 ml of the solution in the presence of a catalytic amount of dimethylformamide.
Heated to reflux for 0 minutes. After distilling off excess thionyl chloride and benzene under reduced pressure, the residue was dissolved in 15 ml of tetrahydrofuran. 0.42 g of triethylamine and the above (1)
1.0 g of 5-trifluoromethyl-2-pyridylmethylamine obtained in 1. was added, the mixture was stirred at room temperature for 18 hours, poured into water and extracted with ethyl acetate. The organic layer was washed with an aqueous solution of ammonium chloride, water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain 0.34 g of the desired product (Compound No. 1) having a melting point of 133.5-137 ° C.

The compounds of general formula (I) prepared according to the present invention are listed in Tables 1 to 3.

[0101]

[Table 1]

[0102]

[Table 2]

[0103]

[Table 3]

Test Example 1 Green peach aphid insecticidal test Each formulation of the active ingredient compound was dispersed in water to adjust the concentration to 800 ppm. After applying an adhesive to the petiole of an eggplant planted in a pot (diameter 8 cm, height 7 cm) in which only one true leaf was left, 2-3 leaves of the peach peach aphid wingless female fetus were inoculated into the true leaf to produce I gave birth to a baby. Two days after the inoculation, the adults were removed and the number of larvae was counted. The eggplant leaves on which the larvae were parasitized were immersed in a chemical solution adjusted to the above concentration for about 10 seconds, air-dried, and then left in a constant temperature room at 26 ° C. with illumination. On the 5th day after the treatment, life or death was judged, and the mortality rate was calculated by the following formula. The detached insects were considered dead.

Mortality rate (%) = number of dead insects / number of treated insects × 100

Compound NO. 1 to 4 and 6 to 21 are 100
% Mortality and compound NO. No. 5 showed a mortality of 90 to 99%.

Test Example 2 Permeation transfer test of green peach aphid Each formulation of the active ingredient compound was dispersed in water to adjust the concentration to 800 ppm. After applying an adhesive to the petiole of a planted eggplant in a pot (8 cm in diameter and 7 cm in height) leaving only one true leaf, inoculate 2-3 leaves of the green peach aphid wingless female fetus into the true leaf. I gave birth to a baby. Two days after the inoculation, the adults were removed and the number of larvae was counted. The larvae of the larvae were parasitized with 10 ml of the chemical solution adjusted to the above-mentioned concentration, and then left in a constant temperature room at 26 ° C. with illumination. After 5 days from the treatment, life or death was determined, and the mortality rate was obtained in the same manner as in Test Example 1 above. The detached insects were considered dead.

Compound No. 1-4, 7, 8, 12 and 1
3 showed 100% mortality.

Next, the formulation examples of the present invention will be described, but the compounds, compounding ratios, dosage forms and the like in the present invention are not limited to the following description examples.

Formulation Example 1 (a) Compound No. 1 20 parts by weight (b) Kaolin 72 parts by weight (c) Sodium lignin sulfonate 8 parts by weight The above ingredients are uniformly mixed to obtain a wettable powder.

Formulation Example 2 (a) Compound No. 45 parts by weight (b) Talc 95 parts by weight The above ingredients are uniformly mixed to obtain a powder.

Formulation Example 3 The above are uniformly mixed and dissolved to prepare an emulsion.

Formulation Example 4 A mixture of the above components and compound No. 5 and 4 are mixed at a weight ratio of 4: 1 to obtain a wettable powder.

Formulation Example 5 And uniformly mix and dry to make a granule wettable powder.

Formulation Example 6 (A) to (C) are uniformly mixed in advance, diluted with an appropriate amount of acetone, and then sprayed on (D) to remove acetone to obtain a granule.

Formulation Example 7 (a) Compound No. 16 2.5 parts by weight (b) N-methyl-2-pyrrolidone 2.5 parts by weight (c) Soybean oil 95.0 parts by weight The above ingredients are uniformly mixed and dissolved to give a trace amount of spray agent (ult).
ra low volume formatulatio
n).

Formulation Example 8 The above are mixed uniformly to form an emulsion.

Formulation Example 9 (a) Compound No. 7 20 parts by weight (b) Lauryl sulfate sodium salt 3 parts by weight (c) Water-soluble starch 77 parts by weight The above components are uniformly mixed to obtain a water solvent.

─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. ⁶ Identification number Internal reference number FI Technical display area A01N 43/78 B 9155-4H 43/80 101 9155-4H C07D 401/12 213 405/12 213 409 / 12 213 413/12 213 417/12 213 (72) Inventor Chiharu Kagimoto 2-3-1 Nishi-Shibukawa, Kusatsu City, Shiga Prefecture Ishihara Sangyo Co., Ltd. Central Research Laboratory

Claims (3)

[Claims] 1. A compound represented by the general formula (I): (In the formula, A is an alkanediyl group, X is an optionally substituted heterocyclic group, R is a hydrogen atom or an alkyl group, provided that when R is a hydrogen atom and A is a methylene group. , X is an unsubstituted pyridyl, the same thienyl and the same furyl)), or a salt thereof. 2. 4-trifluoromethylpyridine-3-
The carboxylic acid or its reactive derivative and the general formula (III):
HN (R) -AX (III) (In the formula, A is an alkanediyl group, X is an optionally substituted heterocyclic group, R is a hydrogen atom or an alkyl group, provided that R is A hydrogen atom and A is a methylene group, X is an unsubstituted pyridyl group, a thienyl group and a furyl group), and a compound represented by the general formula (I) Chemical 2] A method for producing an amide compound represented by the formula (A, X, and R are as described above) or a salt thereof. 3. General formula (I): (In the formula, A is an alkanediyl group, X is an optionally substituted heterocyclic group, R is a hydrogen atom or an alkyl group, provided that when R is a hydrogen atom and A is a methylene group. , X is an unsubstituted pyridyl, the same thienyl and the same furyl)), or a salt thereof as an active ingredient.