JPH03178964A - Pyridylpyridone derivative and use thereof as insecticide - Google Patents

Abstract

NEW MATERIAL:A pyridylpyridone derivative shown by formula l (R is Cl or cyano). EXAMPLE:[1(2H),3-Chloro-5-trifluoromethyl-3',5'-bistrifluoromethyl-2'- bipyridin]-2- one. USE:Useful as an insecticide having excellent insecticidal effects on hemipterous insect pests, dipterous insect pests, Dictyoptera insect pests, hymenopterous insect pests, etc., especially high intake toxicity and showing extremely excellent effects as a poisonous feed for controlling insect pests. PREPARATION:For example, a pyridine derivative shown by formula II is condensed with a pyridone derivative shown by formula III in the presence of a base such as sodium hydroxide at 50-150 deg.C, especially 70-120 deg.C in a solvent such as dimethylformamide to give a compound shown by formula I.

Description

DETAILED DESCRIPTION OF THE INVENTION <Industrial Application Field> The present invention relates to a novel pyridylpyridone derivative and its use as an insecticide.

<Prior art> Until now, Japanese Patent Application Laid-open No. 61-72754, Japanese Patent Application Laid-open No. 63
JP-A-170862 and the like describes that pyridylpyridone derivatives are used as active ingredients of insecticides.

<Problems to be Solved by the Invention> However, these compounds cannot always be said to be sufficient as active ingredients of insecticides, such as insufficient efficacy.

Means for Solving the Problems In view of the above circumstances, the present inventors conducted various studies to develop a better insecticide, and found that a pyridylpyridone derivative represented by the following general formula [D] is It was discovered that it has excellent insecticidal efficacy, leading to the present invention.

That is, the present invention is based on the general formula [■] [wherein R represents a chlorine atom or a cyano group]. ] The present invention provides a pyridylpyridone derivative (hereinafter referred to as the compound of the present invention) represented by the following, an insecticide containing the same as an active ingredient, and an insecticidal method using the same.

The properties of the compound of the present invention when used as an active ingredient of an insecticide are as follows.

1. It has extremely high insecticidal efficacy against various pests.

2. It is also highly effective against pests that are less sensitive to organic agents, carbamates, pyrethroid agents, etc.

3. Expresses extremely high feeding toxicity to pests.

4. Does not exhibit feeding repellent activity against pests due to odor or nerve stimulation.

5. Very low oral toxicity to warm-blooded animals.

Based on the above characteristics, when the compound of the present invention is used as an active ingredient of an insecticide, it may be applied transdermally to the bodies of insect pests by direct or indirect methods, but it can also be used orally as a poison bait composition for pest control. Better insecticidal efficacy can be obtained by administering the insecticide directly.

Among the compounds of the present invention represented by the general formula [I], more preferred are compounds in which R represents a chlorine atom.

The compounds of the present invention can be synthesized by the two methods shown below.

C synthesis method A) By condensing a pyridine derivative represented by the formula [111] and a pyridone derivative represented by the formula [1■] ■ in the presence of a base, a pyridylpyridone derivative represented by the formula [IV] is prepared. How to get it.

Examples of the base include potassium carbonate, sodium hydride, and metallic sodium.

The reaction temperature is 50-150°C depending on the type of base used.
The temperature can be set arbitrarily within this range, but usually a temperature range of 70 to 120°C is sufficient to achieve the purpose.

In this method, the reaction t6 medium is not essential, but a polar solvent can be used to make the reaction proceed more smoothly. Specific examples of such solvents include dimethylformamide, dimethylacetamide, dimethylsulfoxide, and the like.

The amount of the reaction reagent used is usually 0.5 to 2.0 moles of the pyridone derivative represented by the formula QLI per 1 mole of the pyridine derivative represented by the formula 110.

Although the reaction time may vary depending on the type of base used, the reaction temperature, and the presence or absence of a solvent, the objective can usually be achieved within a range of 2 to 48 hours.

(Synthesis method B) A method for obtaining a pyridylpyridone derivative represented by the formula CC] by reacting a pyridylpyridone derivative represented by the formula IJ) with a cyanide compound.

In this method (B), examples of the cyanide compound used include potassium cyanide, sodium cyanide, copper cyanide, and the like.

Usually, the reaction can be carried out in a polar solvent such as dimethylformamide, dimethylsulfoxide, dimethylacetamide, and the like.

The amount of the cyanide compound used is usually 1.0 per mole of the pyridylpyridone derivative represented by the general formula [1■].
~2.0 times the mole, the reaction temperature is 0~100°C, and the reaction time varies depending on the reaction temperature, but is usually 1~2.0 times the mole.
It is 48 hours.

In both synthesis methods (A) and (B), the reaction solution after completion of the reaction can be subjected to conventional post-treatments such as organic solvent extraction and concentration to obtain the desired compound of the present invention.

If necessary, it can be purified by operations such as chromatography and recrystallization.

Examples of pests against which the compounds of the present invention are highly effective include the following.

Hemiptera pests, planthoppers such as the brown planthopper, brown planthopper, and brown planthopper; leafhoppers such as the black leafhopper and black leafhopper; aphids; stink bugs; whiteflies; scale insects; Kameichi □tsu), Kbutsume, Iga, Noshimekokuga hat's Mayga ode, Spodoptera japonica, Fall armyworm,
23 species such as cypress moths, white moths such as cabbage moths, cylindrical moths such as chinensis moths, cylindrical moths, leafminers moths, brown moths, leaf moths, kaburaya moths,
Agrothissp.
p, ), Heliothis sp.
p, ), Diptera pests such as the diamondback moth, burr, and carp moth, Culex mosquitoes such as Culex mosquito, Culex pipiens, Culex mosquito such as Culex pipiens, Aedes mosquitoes such as Aedes albopictus and Aedes albopictus, Anopheles mosquitoes such as Anopheles mosquito, Chironomid mosquitoes, House flies such as house fly, and black fly. Bee flies, fruit flies, melanogaster flies, butterfly flies, horseflies, black flies, sand flies, etc.; Western: - rootworms, southern corn rootworms, etc. Scarab beetles such as corn rootworms, brown beetles, and corn rootworms; corn beetles such as corn weevils and rice water weevils; meal beetles such as brown corn rootworms and corn rootworms; potato beetles such as yellow beetles and cucumber beetles; genus ()le
nosuepilachna spp, ), Japanese beetles, long beetles, longhorn beetles,
Ophthalmopteran pests, such as the German cockroach, black cockroach, American cockroach, Japanese cockroach, Common cockroach, etc., Hymenoptera pests, such as the southern yellow thrips, Hana thrips, etc., ants, wasps, wasps, and insect pests. It is highly effective against Orthoptera pests such as haptic bees and other haptic insects, cryptopteran pests such as mole crickets and grasshoppers, lice pests such as human fleas, isoptera pests such as human lice and pubic lice, Japanese termites, house termites, etc.

When using the compound of the present invention as an active ingredient of an insecticide,
Usually, it is mixed with a solid carrier, liquid carrier, gaseous carrier, bait, or impregnated into a base material such as mosquito coil, ma, soto, etc., and if necessary, surfactants and other formulation auxiliaries are added. Flowable agents such as oils, emulsions, wettable powders, suspensions and emulsions in water, granules, powders, aerosols, heating fumigants such as mosquito coils, electric mosquito mats, and no-mats, and self-combustion types. (
Heating smoke agents such as scorching agents, chemical anti-Ib type smoke agents, porous ceramic plate smoke agents, non-heating transpiration agents such as resin transpiration agents and impregnated paper evaporation agents, fogging agents such as fogging, LJLV agents, micro Used in capsules, poison baits, etc.

Cholera preparations usually contain 0.01 to 95% by weight of the compound of the present invention as an active ingredient.

Solid carriers used in formulation include, for example, clays (kaolin clay, diatoms, synthetic hydrous silicon oxide, bentonite, fubasamikle, acid clay, etc.), talcs,
Fine powders or granules such as ceramics, other inorganic minerals (sericite, quartz, sulfur, activated carbon, calcium carbonate, hydrated silica, etc.), chemical fertilizers (ammonium sulfate, ammonium phosphorus, ammonium nitrate, urea, ammonium chloride, etc.) Liquid carriers include, for example, water, alcohols (methanol, ethanol, etc.), ketones (acetone, methyl ethyl ketone, etc.), aromatic hydrocarbons (benzene, toluene, xylene, ethylbenzene, methylnaphthalene, etc.), aliphatic Hydrocarbons (hexane, cyclohexane, kerosene, light oil, etc.), esters (
ethyl acetate, butyl acetate, etc.), nitriles (acetonitrile, isobutyronitrile, etc.), ethers (diisopropyl ether, dioxane, etc.), acid amides (N, N
- dimethylformamide, N,N-dimethylacetamide, etc.), halogenated hydrocarbons (dichloromethane, trichloroethane, carbon tetrachloride, etc.), dimethyl sulfoxide, vegetable oils such as soybean oil, cottonseed oil, etc. are added to the gaseous carrier, i.e., injection Examples of the agent include chlorofluorocarbon gas, butane gas, LPG (liquefied petroleum gas), dimethyl ether, carbon dioxide gas, and the like.

Examples of the surfactant include alkyl sulfates, alkyl sulfonates, alkylaryl sulfonates, alkylaryl ethers and their polyoxyethylenic products, polyethylene glycol ethers, polyhydric alcohol esters, sugar alcohol m-conductors, etc. Kaac
f be beaten.

Formulation auxiliaries such as fixing agents and dispersants are used, for example, casein, gelatin, polysaccharides (starch powder, gum arabic, cellulose derivatives, alginic acid, etc.), lignin-containing agents, etc.
Examples of stabilizers include P. acetate, bentonite, sugars, and synthetic water bathing polymers (polyvinyl alcohol, polyvinylpyrrolidone, polyacrylic acids, etc.).
P (acidic isopropyl phosphate), BHT (2,6-di-tert-butyl-4-methylphenol), B)
iA (a mixture of 2-tert-butyl-4-methoxyphenol and 8-tert-butyl-4-methoxyphenol), mint oil, mineral oil, surfactants, fatty acids or esters thereof, and the like.

Examples of the base material for mosquito coils include mixtures of raw plant powders such as wood flour and lees powder and binders such as tab flour, starch, and gluten.

Examples of the base material for electric mosquito repellent mats include cotton linters or fibrils of a mixture of cotton linters and pulp solidified into a plate shape (Q).

The base materials for self-combusting smoke agents include, for example, combustion exothermic agents such as nitric acid, salts of nitrate, guanidine salts, potassium chlorate, nitrocellulose, ethyl cellulose, and wood powder, alkali metal salts, and alkaline earth metal salts. , thermal decomposition stimulants such as dichromate, chromate, oxygen supply agents such as potassium nitrate,
Combustion agents such as melamine, wheat starch, etc., fillers such as diatoms, binders such as synthetic glues, etc.

The base materials for chemically reactive smoke agents include, for example, exothermic agents such as alkali metal sulfides, polysulfides, hydrosulfides, hydrated salts, and calcium oxide, and catalyst agents such as carbonaceous substances, iron carbide, and activated clay. , organic blowing agents such as azodicarbonamide, benzenesulfonyl hydrazide, dinitrosopentamethylenetetramine, polystyrene, polyurethane, natural fiber pieces,
Examples include fillers such as synthetic fiber pieces.

Examples of the base material of the non-heating transpiration agent include thermoplastic resin,
Examples include filter paper and Japanese paper.

The formulation of flowables (suspensions or emulsions in water) generally consists of 1 to 75% of the compound, 0.5 to 15% of dispersing agents, 0.1 to 10% of suspending aids (e.g. Compounds that impart colloidal and thixotropic properties) to 0/10%
appropriate auxiliary agents (for example, antifoaming agents, rust agents, 9
．． Disperse finely in water containing a stabilizer, a spreading agent, a soaking agent, an antifreeze agent, an antibacterial agent, an antifungal agent, etc.)
You can get it with Bru. It is also possible to use an oil in which the compound hardly melts instead of water and use it as a suspending agent in the oil. 4i
u a v u i! As number, 'L s 7J, ,
! : 2L-colatin, casein, cams, 7-J-sue-nal, 4ζ-rivinyl alcohol, etc. are used. Thixo l
Materials 7 (゛, t, for example, aluminum, magnesium silicate, r -1 = % xanthan gum, polyacrylic acid, etc.) are obtained.

・-? The ilO substance of the iclocapsenolytic agent is, for example, 1) flare, polyurethane, polyamide, polyester, polycarbonate, polysulfone.
I would like to mention polysulfonamide, uboxy sulfate 17, etc. Further, as a method for producing macrocabucells, an interfacial polymerization method is preferable.

As for the form of microcapsules, the average particle size is 1 to 10
It is preferable that the particle size/film thickness ratio is 10 to 140.

Examples of the base materials for poison bait include the following: Edible ingredients or feeding attractants include vegetable oils: potato flour, sweet potato flour, corn flour, wheat flour, rice flour, taro flour, starch powder, cellulose powder, wood flour, bark powder, nematode powder, etc. Soybean oil, rapeseed oil, coma oil, wheat germ oil, corn oil, castor oil, bean oil, cottonseed oil, coconut oil, olive oil, palm oil, tall oil, etc. Vegetables: potato, sweet potato, taro, garlic, onion, malt , rice bran, wheat bran, etc. Plant processed products: (crystalline) cellulose, dextrin, solid animal breast feed (powder), etc. Animal bodies: Chicken and egg paste Animal processed products: Fish meal, pupa meal, krill meal, shrimp meal, egg meal Processed foods such as meat extracts: powdered milk, milk, biscuits, alcoholic beverages, etc. Proteins: albumin, globulin, casein, various amino acids, etc. Fats such as cane juice, blackstrap molasses, honey, etc. Acid, stearic acid, etc. Flavor: Cheese flavor, butter flavor, peanut flavor, beach flavor, strawberry flavor, milk flavor, onion flavor, etc. Chemical attractants: a-oxy acid, α-oxyester, α-
Ketol, ar-α-tetralol, #,, spoon ÷ 1 lalor α-naphthol, β-naphthol, furaneol (4-hydroxy 2,5-dimethyl-3-(2H) furanone), 4,5-dihydroxy-25 -dimethyl-4-oxo-3-furanyl methyl ester, 4,5-dihydroxy-2,5 dimethyl-4-oxo-3-furanyl ethyl ester, 2-cyclohexyl-5-methyl-3-(2 H) Furanone, 4-acetyl-5 methyl-8-(2H) furanone, 2.5-dimethyl-3-(2H') furanone, etc. Aggregation pheromone: 1-dimethylamino-2-methyl 2
- propatool and its hydrochloride, formate, acetate, oxalate or stearate, l-amino-2-methyl-2-proparal, l-diethylamino-2 methyl-2-propanol, ■ methylamino- 2-Methyl-2 propatool, its amine compound, etc. Bepheromone: (3S, 4R, 6E, lOZ)-8,4゜7.11
-tetramethyl-trideca6.10-genal, (Z)-9 hexadecenal, 2,5-dimethylpyrazine, 3-methyl-2゜5-dimethylpyrazine, Z, E α-furanesene, E, E-a -Franesene, etc. 1IlI quantity agents include silica gel, silicic acid, diatom-42, kaolin, talc, clay, highly dispersed silicic acid, white carbon, bentonite, zeolite, sepiolite, acpulgite, etc. Binders include iridge moss, tragacanth gum, karaya gum , carboxymethylcellulose sodium, methylcellulose,
Antioxidants such as hydroxypropylcellulose and tababu include erythorbic acid, sodium erythorbate, dibutylhydroxytoluene, dl-α-tocopherol, nordihydroguaiaretic acid, methylhydroxyanisole, propyl gallate, guaiac butter, and L- Preservatives such as cysteine hydrochloride and butylhydroxyanisole include benzoic acid, sodium benzoate, salicylic acid, diphenyl, sorbic acid, potassium sorbate, dehydroacetic acid,
Sodium dehydroacetate, isobutyl halaoxybenzoate, isopropyl paraoxybenzoate, ethyl paraoxybenzoate, butyl paraoxybenzoate, propyl paraoxybenzoate, calcium propionate, sodium propionate, 2-hydroxydiphenyl, etc. As agents to prevent accidental ingestion, chili pepper Amaranth, Amaranth Aluminum Lake, Erythrosin, Erythrosin Aluminum Lake, Newcoccin, Phloxin, Rose Bengal, Acid Red, Tartrazine, Tartrazine Aluminum Lake, Sunset Yellow FCF, Sunset Yellow FCF Aluminum Lake, Fast Green)' C
F, Fupst Green FCF Aluminum Lake, Brilliant Blue FCF, Brilliant Blue FCF Aluminum Lake, Indigo Carmine, Indigo Carmine Aluminum Lake, β-carotene, Copper Chlorophyll, etc.

Coloring agents include Lysor Parvin, Lake Red, Lysole Red, Rhodamine, Tetrachlorotetrabromofluorescein, Brilliant Lake Red, Deep Maroon, Toluidine Red, Herringdon Pink, Fast Acinodomagen, Permaton Red, Eosin, Violamine, Brilliant Fast. Scarlet, permanent red, oil red, fast red, azo dye, phthalocyanine dye, red January, etc.

The preparation thus obtained can be used as is or diluted with water or the like. In addition, other insecticides, acaricides,
It can also be used simultaneously with or without mixing with nematicides, soil pest control agents, fungicides, herbicides, plant growth regulators, synergists, fertilizers, and soil conditioners.

When the compound of the present invention is used as an active ingredient of an agricultural insecticide, the application rate is usually 5 to 500 f/lO are.
When applying emulsions, wettable powders, flowable agents, etc. diluted with water, the application concentration is 10 to 2000 ppm.
Therefore, granules, powders, etc. are applied as they are without any dilution. In addition, when used as an effective biocide for home and epidemic prevention, emulsions, wettable powders, flowables, etc. should be diluted with water to 10 to 10,000 ppm before application, and oils, aerosols, fumigants, etc. Fumigants, transpiration agents, atomizing agents, microcapsules, ULV agents, poison baits, etc. can be applied as is.

These application amounts and concentrations vary depending on the type of formulation, application time, application location, application method, type of pest, degree of W coverage, etc., and may be increased or decreased regardless of the above range. You can

<Examples> Hereinafter, the present invention will be explained in more detail with reference to production examples (reference examples), formulation examples, and test examples, but the present invention is not limited to these examples.

First, a production example of the compound of the present invention will be shown.

Production Example 1 (Synthesis Method A) [Production of Compound (1,) of the Present Invention] Sodium hydride 100 m? (60%) was added to dimethylformamide 10-, to which 3chloro=5
-Trifluoromethyl-2-pyridone 5 (10ml) was added at 20°C, stirred for 10 minutes, and then
-chloro-3,5-bistrifluoromethylpyridine 6
00■ was added and stirred at 100°C for 24 hours. After cooling the reaction solution, it was poured into ice water and extracted with ethyl acetate. After washing the ethyl acetate layer with brine, the bath medium was distilled off, and the resulting residue was subjected to silica gel column chromatography to obtain [1(2H), 8-chloro5-trifluoromethyl-
8',5'-bistrifluoromethyl-2'-bipyridine-2-one (compound of the present invention (1,)) 790
my was obtained as white crystals (yield 76%).

Melting point LO2, 4°C NMR (δ value, deuterochloroform) 7.68 (m, 11() 7.76 (d, LH) 8.42 (br, s, 18) 9.98 (br, s, LH ) Production Example 2 (Synthesis method B) (Production of compound (2) of the present invention) 1.44 da of 2-one was dissolved in 15-dimethyl sulfoxide, 0.87 g of potassium cyanide was added, and the mixture was stirred at 30°C for 24 hours.The reaction solution was poured into water, and the aqueous layer was diluted twice with ethyl acetate. I put it out.

The ethyl In acid layer was washed once with brine and then dried over anhydrous magnesium sulfate. After distilling off the bath medium, the obtained dark red oil was subjected to silica gel column chromatography, and the developing bath medium n-hexane:ethyl acetate-3; -5-trifluoromethyl-3',5'-bistrifluoromethyl-2-bipyridine-2-one (compound of the present invention (2)) 1.01
f/ was obtained as white crystals (yield 72 L20).

Melting point 159.3°C NMR (δ value, deuterated chloroform) 7,88 (m, L H) 8.02 (d, LH) 8.41 (br, s, L H) 9.04 (br, s, IH) Next, formulation examples are shown. In addition, the compounds of the present invention are indicated by the compound number in the manufacturer, and parts represent parts by weight.

Formulation Example 1 Emulsion 10 parts of each of the compounds (1) or (2) of the present invention were dissolved in 35 parts of xylene and 35 parts of dimethylformamide,
Add to this 1 polyoxytyrene styryl phenyl ether
Add 4 parts of calcium dodecylbenzenesulfonate and 6 parts of calcium dodecylbenzenesulfonate, and mix with stirring to obtain each t096 emulsion.

Formulation Example 2 Wettable powder 20 parts of the compound of the present invention (1) was added to a mixture of 4 parts of sodium lauryl sulfate, 2 parts of calcium lignin sulfonate, 20 parts of synthetic hydrated silicon oxide fine powder, and 54 parts of diatomaceous earth, and mixed with a juice mixer. Stir and mix to obtain 20q6 hydrating agent.

Formulation Example 3 Granules 5 parts of synthetic hydrous silicon oxide fine powder, 5 parts of sodium dodecylbenzene sulfonate, 30 parts of bentonite, and 55 parts of clay are added to 5 parts of the compound of the present invention (2), and the mixture is thoroughly stirred and mixed. Then, an appropriate amount of water is added to the mixture, which is further stirred, granulated using a granulator, and dried through ventilation () to obtain 596 granules.

Formulation Example 4 I part of the uninvented compound (1) was dissolved in an appropriate amount of acetic acid, 5 parts of synthetic a silicon hydroxide fine powder, 141093 parts and 98.7 parts of clay were added. - Stir and mix at - and remove acetone by evaporation.1. Shrine the shaped powder.

Formulation Example 5 Flowable Compound of the Invention (2>20 parts and Solhitant Triolet!
-1-1,5W tow, mixed with 28.5 parts of water > 8 liquid containing 2 parts of hollyvinyl alcohol, finely pulverized with a sand grinder (particle size 8μ or less), and in this, xanthan gum 0 0.05 parts of aluminum magnesium silicate and 40 parts of aqueous solution containing 0.1 part of aluminum magnesium silicate were added, and further 10 parts of propylene glycol were added and mixed with stirring.
) also gives a suspension in water.

Formulation Example 6 Oil Inventive Product (t > o, i part is trichloroethane 1
This was mixed with 89.9 parts of deodorized kerosene to make o.
, to obtain i-bin oil.

Formulation Example 7 Oil-based aerosol Compound of the present invention (2) 0.1 part, Tetramethrin 0.2
parts, 0.1 parts of d-phenothrin, 10 parts of trichloroethane
After mixing and dissolving 59.6 parts of deodorized kerosene and filling it into an aerosol container and attaching a valve part, 30 parts of a propellant (liquefied petroleum gas) is pressurized and filled through the valve part to obtain an oil-based aerosol. .

Formulation Example 8 Aqueous aerosol Compound of the present invention (1) 0.2 parts, d-allethrin 0.2
0.2 parts of d-phenothrin, 5 parts of xylene, 3.4 parts of deodorized kerosene, 11 parts of an emulsifier (Atmos 800 (registered trademark of Atlas Chemical Co.)), and 50 parts of pure water were placed in an aerosol container. Fill the tank, attach the valve part, and inject the propellant (liquefied petroleum gas) through the valve part.
40 parts were filled under pressure to obtain an aqueous aerosol.

Formulation Example 9 Mosquito coil Compound of the present invention + 2) 0.3 y and d-allethrin 0.
81 and bath-dissolved in 2Q ml of acetone to prepare a carrier for mosquito coils (mixing tab: lees powder: wood flour in the ratio of 4:8:8).
After uniformly stirring and mixing 99.41/ml of the mixture, 120% of water was added, the mixture was thoroughly kneaded, and the mixture was molded and dried to obtain a mosquito coil.

Formulation Example 10 Electric mosquito repellent cloak Compound of the present invention (1) 0.4y, d-allethrin 0.41
Then, acetone is added to 0.4 g of piperonyl butoxide and dissolved to give a total of 10-.

0.5 ml of this bath solution is 2.5 cm x 1.5 c
An electric mosquito repellent mat agent is obtained by uniformly impregnating a base material for an electric cloak (fibrils of a mixture of cotton linter and pulp solidified into a plate shape) with a thickness of 0.8 cm.

Formulation Example 11 Heat Smoking Agent Inventive Compound (2) 100'r was dissolved in an appropriate amount of acetone, impregnated into a porous ceramic plate measuring 4.0 cm x 4.0-1 and 1.2-cm thick, and heated. Obtain smoking agent.

Formulation Example 12 30η of each of compound (1) or (2) was mixed with 0 of acetone,
The solution is dissolved in a bath for 5 hours, and this solution is uniformly applied to pieces (3 g) of solid feed for animals (solid feed for captive breeding CE-2, trade name of Nippon Yurea Co., Ltd.). The acetone was then air-dried to obtain 1% poisoned bait for each.

Formulation Example 13 20rn/each of compound (1) or (2) was added to
0,5 + nl, and this bath solution was used for animal use.
! d-type feed powder CE-2, Nippon Yurea Co., Ltd. product name)
Process to 5g and mix uniformly. The acetone was then air-dried to obtain each 0.496 poison bait.

Formulation Example 14 60 parts of compound (1) and 40 parts of highly dispersed silicic acid are stirred and mixed in a stirrer. By mixing 0.84 parts of this premix with 0.75 parts of methylcellulose and 98.41 parts of sucrose at room temperature and then milling the mixture,
．． Obtain 5% water-dispersible poison bait.

Formulation Example 15 Compound (2) l 0 parts and linoleic acid 10 parts (purity 65
%) is heated at 60° C. until a clear bath liquid is obtained. 80 parts of soybean oil is added to this mixture, stirred, and then cooled to room temperature to obtain a 10% liquid poison bait.

Formulation Example 16 A mixture of 0 parts of compound (1) l and 15 parts of oleic acid 6. is heated at 80°C until a customs bath liquid is obtained. 75 parts of soybean oil was added to this mixed solution, stirred, and then cooled to room temperature to obtain a poisonous bait with an IO%;'i+ shape.

Formulation Example 7 Add an appropriate amount of water to 1 part of compound (2), 70 parts of sucrose, 27 parts of pupa flour, and 2 parts of hydroxymethyl cellulose, and stir and mix uniformly. This mixture is granulated with an average of 1.
After granulating into orrl and drying the water, one part of granular poison bait is obtained.

Formulation example ■8 Compound (L) 1 part, Hachi 5770 parts, Telami grains 27
1 part and 2 parts of hydroxymethylcellulose are uniformly mixed by stirring.

This mixture is granulated to an average size of 1.5 J using a granulator and then dried to obtain a 1% granular poison bait.

Formulation Example 19 0.5 parts of compound (2) and 8 parts of goji oil were mixed, and to this was added 5 parts of brown sugar, 30 parts of crystalline cellulose, 61.37 parts of potato starch, and 0.0 parts of butylhydroxyanisole.
Add 3 parts and 0.1 part of dehydroacetic acid and mix uniformly. This mixture is compressed into tablets of about 4 y (30 in diameter) to obtain 0.5% poisoned bait.

Formulation Example 20 Mix 0.8 parts of compound (1) and 5 parts of corn oil, and add 22 parts of brown sugar, 35 parts of crystalline cellulose, 81.58 parts of corn starch, and 0.02 parts of nordihydroguaiaretic acid. part, dehydroacetic acid 0, 1 part, furaneol (
Add 5 parts of 4-hydroxy-2<5-dimethyl-a(2n)furanone) and 0.5 part of chili pepper powder and mix uniformly.

This mixture is compressed into tablets of about 1' (diameter 30 mm) to obtain 0.8% poisoned bait.

Formulation Example 21 30 μm of each of compound (L) or (2) was mixed with 0.0 μm of acetone.
8-, and process this solution into a mixture of skim milk powder 2y and granulated sugar ly, and mix uniformly. Then air dry the acetone to obtain 1% poisoned bait.

Formulation Example 22 10q of each of compound (1) or (2) was added to 1-10q of acetone.
The solution is dissolved in a bath, and the bath solution is treated with lOy of granulated sugar.
Mix evenly. The acetone is then air-dried to obtain 0.1% poisoned bait.

Formulation Example 28 2 parts each of compound (1) or (2), dextrin 9
4.9 parts, dehydroacetic acid 0.1 part and furaneol (
3 parts of 4-hydroxy-2,5-dimethyl-3(2H)furanone) were mixed uniformly. Add 15kQ/
- Pressure is applied to form a tablet into a tablet of about 4y (diameter 30mm) to obtain each 296 poison bait.

Formulation Example 24 5 parts each of compound (L) or (2) obtained by microencapsulating polyurethane using a membrane material, 9 parts of dextrin
4.9 parts and 01 part of dehydroacetic acid are uniformly mixed.

A pressure of 15 kq/l:d was applied to this mixture, and one tablet was approximately 4
! They were compressed into tablets (30 holes in diameter), each containing 0.5% poison [14
get.

Next, test examples demonstrate that the compounds of the present invention are useful as active ingredients of insecticides. The compounds used for comparison are indicated by compound symbols in Table 1.

Table 1 Compound symbol Chemical structural formula: Remarks Test example 1 (Insecticidal test against house fly) Diameter 5.5 m
A filter paper of the same size was placed on the bottom of a polyethylene cup, and an emulsion of the test compound obtained according to Formulation Example 1 was mixed with water.
00 times diluted solution (100 ppm) 0.7-1. was dropped onto a paper plate, and 301ηy of sucrose was added uniformly as bait. Ten female adult King flies were released into the chamber, the lid was closed, and 48 hours later, their survival and death were determined to determine the mortality rate (2 replicates). The results are shown in Table 2.

Table 2 Test compound Mortality rate (%) (+,) 1.00 (2) l 00 Untreated 0 g1ffllJ2<Insecticidal test against black leafhopper) Formulation example 1 was an emulsion of the OL test mixture obtained in Kurashiki. Rice stems (
(length: approximately 12 m) was immersed for 1 minute.

After air-drying, the rice stems were placed in a test tube, and 10 adult brown planthoppers were released.One day later, their survival and death were investigated to determine the mortality rate (2 repetitions)6.The results are shown in Table 3.

Table 3 Test Compound Mortality Rate (%) (1) l O0 No treatment, 5 Test Example 3 Poisoned bait of test compound obtained according to Formulation Example 13, active ingredient concentration 0. 1%) was used for the following tests.

In a polyethylene cup (diameter 12z, height 7crn), 20 adult German cat cypresses (10 males and 10 females) of a biocide-insensitive strain were released (1 g of the above poisoned bait and 1 g of untreated bait were placed in each). Another plastic camp (i
+'f diameter 3m, height 2cm), place a filter paper shelter (8zX7α) and a water supply source, 25''
Hold at C. Three weeks after release, the test insects were examined for life or death, and the mortality rate was determined (two repetitions).

The results are shown in Table 4.

Table 4 Test compound Mortality rate (%) (1) l 00 (A') 87.5 (B)
45 No treatment 0 Test example 4 Plastic container (61m x 40m, height l 4
．． A wooden shelter (15zX
15 m, height 8 cm) and a water source, and 20 adult American cockroaches (10 males and 10 females) were released. After 1 day, 0.49% of the test compound obtained according to Formulation Example 18
6. 3 g of poison bait was placed in a polyethylene cup (diameter 6 cm, height 3 crn) and placed in the l corner of the container. remaining 3
In the corner, 3 yards of the same formula Q) untreated stretch bait was placed in a 31-round polyethylene cup (same size).

I continued to investigate the life and death of cockroaches from time to time, checking the number of cockroaches until I reached Kanayama's death Q.

The amount of poisoned bait ingested 21 days after the bait was placed was calculated as a relative value to that of the rats eating the untreated bait. The relative value of recreational food intake is calculated by the following formula.

The results are shown in Table 5.

Table 5 Test Example 5 Test compound obtained in Formulation Example 22) 0) 0.1%
The following test was conducted using poisoned bait.

Polyethylene cup (diameter 9.5 ryr, height 4,
5 m), 10 black wood ant menaces were released, and 0.3 g of the poisoned bait described above in a plastic cap (2 m in diameter, 1 cm in height) and a water source were placed.

After release 2[), survival and death were investigated and the mortality rate was determined (2 repetitions).

The results are shown in Table 6.

Table 6 Test compounds Mortality rate (%) (2)l O0 (A) 85 (B) 45 No treatment 0 <Effects of the invention> The compounds of the present invention are effective against Hemiptera pests, Diptera pests, and reticulata. It has an excellent insecticidal effect against insect pests of the order Hymenoptera and insects of the order Hymenoptera, and has particularly high feeding toxicity, so it exhibits extremely good efficacy as a poison bait for pest control.

41 completed)

Claims (6)

[Claims] (1) General formula ▲Contains mathematical formulas, chemical formulas, tables, etc.▼ (In the formula, R represents a chlorine atom or a cyano group. Was. ) A pyridylpyridone derivative represented by (2) Formula ▲Contains mathematical formulas, chemical formulas, tables, etc.▼ The pyridylpyridone derivative according to claim 1, which is represented by: (3) An insecticide comprising the pyridylpyridone derivative according to claim 1 as an active ingredient. (4) A poison bait composition for controlling pests, which contains the pyridylpyridone derivative according to claim 1 as an active ingredient. (5) An insecticidal method using the pyridylpyridone derivative according to claim 1. (6) A method for using a poison bait composition for pest control using the pyridylpyridone derivative according to claim 1.