JPH0469B2 - - Google Patents

Description

[Detailed description of the invention]

The present invention relates to formula (I) The present invention relates to a pyridylpyridone derivative represented by the formula and an insecticide containing the same as an active ingredient. Until now, the only known biological activities of pyridylpyridone derivatives are anti-inflammatory and analgesic effects (Japanese patents 6803, 196; 6720, 294;
6720, 295). The present inventors conducted research on the synthesis of new agricultural chemicals and found that a pyridylpyridone derivative represented by formula (I) (hereinafter referred to as the compound (I) of the present invention) has extremely high insecticidal efficacy. 2. Extremely effective against insecticide-resistant pests. They discovered that it has excellent properties such as, and completed the present invention. Specific pests to which the compound (I) of the present invention is particularly effective include Hemiptera such as planthoppers, Lepidoptera such as armyworms, Diptera such as Culex mosquitoes and houseflies, and Reciptera such as the German cockroach. Can be mentioned. The method for synthesizing the compound (I) of the present invention is as follows:
For example, (1) a method in which 2,3-dichloro-5-trifluoromethylpyridine is heated with anhydrous sodium acetate in dimethylformamide. (2) By heating 2,3-dichloro-5-trifluoromethylpyridine and 3-chloro-5-trifluoromethyl-2-pyridone sodium salt in dimethylformamide in the presence of a copper catalyst. Can be easily synthesized. Synthesis examples will be shown below using reference examples. (Reference Example 1) Add 4.0 g of 2,3-dichloro-5-trifluoromethylpyridine and 1.9 g of anhydrous sodium acetate to 15 ml of dry dimethylformamide,
Stir at ℃ for 8 hours. The reaction solution was poured into ice water and extracted with ethyl acetate. The ethyl acetate layer was washed with brine and then dried over anhydrous magnesium sulfate. After distilling off the ethyl acetate, it was subjected to silica gel column chromatography (developing solvent: n-hexane:ethyl acetate = 20:1), and [1(2H),3-chloro-5-trifluoromethyl-3'- 1.2 g of chloro-5'-trifluoromethyl-2'-bipyrylidin]-2-one was obtained as white crystals. Melting point 108.5-109.0℃ PMR (internal standard: tetramethylsilane, δ value, solvent: deuterium chloroform) 7.77 (2H, S), 8.19 (1H), 8.77 (1H) 1R 1680cm ^-1 (carbonyl) Elemental analysis C% H % N% Cl% Actual value 38.33 1.16 7.46 18.62 (Calculated value 38.22 1.07 7.43 18.83) As C ₁₂ H ₄ Cl ₂ F ₆ N ₂ O (Reference example 2) 100 mg (62%) of sodium hydride was dissolved in dried dimethylformamide 10ml plus 3-chloro-
500mg of 5-trifluoromethyl-2-pyridone
Added at 20°C. After stirring for 15 minutes, 660 mg of 2,3-dichloro-5-trifluoromethylpyridine,
20 mg of cuprous chloride was added and stirred at 140-150°C for 5 hours. It was poured into ice water and extracted with ethyl acetate.
After washing the ethyl acetate layer with brine and evaporating the solvent,
The product was subjected to silica gel column chromatography (chromatography conditions were the same as in Reference Example 1) to obtain 350 mg of the desired product as white crystals. When the compound (I) of the present invention is used as an active ingredient of an insecticide, it may be used as it is without adding any other ingredients, but it is usually used in combination with a solid carrier, liquid carrier, gaseous carrier, or surfactant. , other formulation auxiliaries, etc., mixed with feed, etc., or impregnated into base materials such as incense sticks and mats, to produce emulsions, wettable powders, powders, granules, etc.
It is formulated into oil solutions, aerosols, heating fumigants such as mosquito coils and electric mosquito repellents, fogging agents such as fogging, non-heating fumigants, poison baits, etc. These preparations contain 0.01% to 95% by weight of the compound of the present invention as an active ingredient. Examples of solid carriers include fine powders or granules such as kaolin clay, attapalgite clay, bentonite, acid clay, pyrophyllite, talc, diatomaceous earth, calcite, corn cob powder, walnut shell powder, urea, ammonium sulfate, and synthetic hydrous silicon oxide. Liquid carriers include aliphatic hydrocarbons such as kerosene and kerosene, aromatic hydrocarbons such as benzene, toluene, xylene, and methylnaphthalene, halogenated hydrocarbons such as dichloroethane, trichloroethylene, and carbon tetrachloride, and methanol. , alcohols such as ethanol, isopropanol, ethylene glycol, and cellosolve; ketones such as acetone, methyl ethyl ketone, cyclohexanone, and isophorone;
Examples include ethers such as diethyl ether, dioxane, and tetrahydrofuran, esters such as ethyl acetate, nitriles such as acetonitrile and isobutyronitrile, acid amides such as dimethylformamide and dimethylacetamide, and vegetable oils such as dimethyl sulfoxide, soybean oil, and cottonseed oil. . Gaseous carriers include fluorocarbon gas, LPG (liquefied petroleum gas),
Examples include dimethyl ether. emulsification, dispersion,
Surfactants used for wet spreading, etc.
Alkyl sulfate salt, alkyl (aryl)
Anionic surfactants such as sulfonates, dialkyl sulfosuccinates, polyoxyethylene alkylaryl ether phosphate ester salts, naphthalene sulfonic acid formalin condensates, polyoxyethylene alkyl ethers, polyoxyethylene polyoxypropylene block copolymers, Examples include nonionic surfactants such as sorbitan fatty acid ester and polyoxyethylene sorbitan fatty acid ester. Formulation aids such as fixing agents and dispersants include lignin sulfonate, alginate, polyvinyl alcohol, gum arabic, molasses, casein, gelatin, CMC (carboxymethyl cellulose), pine oil, agar, etc., and are stable. Agents include alkyl phosphates such as PAP (isopropyl acid phosphate) and TCP (tricresyl phosphate), vegetable oil,
Epoxidized oil, surfactants mentioned above, BHT, BHA
, fatty acid salts such as sodium oleate and calcium stearate, and fatty acid esters such as methyl oleate and methyl stearate. Examples of formulations are shown below. In addition, in the following formulation examples, parts indicate parts by weight. Formulation Example 1 0.2 parts of the compound (I) of the present invention, 2 parts of xylene and 97.8 parts of white kerosene are mixed to obtain an oil solution. Formulation Example 2 10 parts of the compound (I) of the present invention, 14 parts of polyoxyethylene styrylphenyl ether, 6 parts of calcium dodecylbenzenesulfonate and 70 parts of xylene are thoroughly mixed to obtain an emulsion. Formulation Example 3 20 parts of the compound (I) of the present invention, 10 parts of fenitrothion
3 parts of calcium lignin sulfonate, 2 parts of sodium lauryl sulfate, and 65 parts of synthetic hydrated silicon oxide.
Thoroughly grind and mix the two parts to obtain a wettable powder. Formulation Example 4 1 part of the compound (I) of the present invention, 2 parts of carbaryl,
87 parts of kaolin clay and 10 parts of talc are thoroughly ground and mixed to obtain a powder. Formulation Example 5 5 parts of the compound (I) of the present invention, 1 part of synthetic hydrated silicon oxide
1 part, 2 parts of calcium lignin sulfonate, 30 parts of bentonite and 62 parts of kaolin clay are thoroughly ground and mixed, water is added and the mixture is thoroughly kneaded, followed by granulation and drying to obtain granules. Formulation Example 6 0.05 part of the compound (I) of the present invention, tetramethrin
Mix and dissolve 0.2 parts of Resmethrin, 0.05 parts of xylene, and 32.7 parts of deodorized kerosene, fill it into an aerosol container, attach the valve part, and then pressurize and fill 60 parts of propellant (liquefied petroleum gas) through the valve part. Then you get an aerosol. Formulation Example 7 Add 5-propargylfurfuryl-d-cis, 0.5 g of transchrysansemate, and 0.5 g of BHT to 1 g of the compound (I) of the present invention, dissolve in an appropriate amount of acetone, and prepare a 4.0 cm x 4.0 cm, thickness 1.2 If it is evenly adsorbed onto a cm porous ceramic plate, a hot smoking agent will be obtained. These preparations can be used as is or diluted with water. It can also be used in combination with other insecticides, acaricides, nematicides, fungicides, herbicides, plant growth regulators, fertilizers, soil conditioners, etc. When the compound (I) of the present invention is used as an insecticide, the application amount is usually 5 g to 10 are.
500g, and when applying emulsions, wettable powders, etc. diluted with water, the application concentration is 10ppm to 1000ppm.
Powders, granules, oils, aerosols, etc. are applied as they are without any dilution. Next, a test example is shown. The compounds used for comparison are indicated by the compound symbols in Table 1.

[Table] Test Example 1 Place paper of the same size on the bottom of a polyethylene cup with a diameter of 5.5 cm, and dilute the emulsion of the compound (I) of the present invention and the control compound obtained in Formulation Example 2 with water to a predetermined concentration of 0.7. ml was dropped onto the paper. As bait, 30 mg of sucrose was placed on the paper. Ten female adult house flies of the insecticide-resistant strain were released into each container, the lids were closed, and 48 hours later, the survival rate was determined to determine the mortality rate (2 repetitions). The results are shown in the table below.

[Table] Test Example 2 Compound (I) of the present invention obtained by Formulation Example 2
Rice stems (12 cm in length) were immersed for 1 minute in a diluted emulsion of the control compound and a control compound with water at a predetermined concentration. After air-drying, the rice stems were placed in a test tube, 10 adult brown planthoppers were released, and one day later, they were examined to see if they were alive or dead, and the LC50 value (50% lethal concentration) was determined (2 repetitions). The results are shown in the table below.

[Table] Test Example 3 A piece of paper of the same size was placed at the bottom of a polyethylene cup with a diameter of 5.5 cm, and the emulsion of the compound (I) of the present invention and the control compound obtained in Formulation Example 2 was diluted with water at a predetermined concentration of 0.7. ml was dropped onto the paper. As bait, 30 mg of sucrose was placed on the paper. We released 10 male German cockroaches into the container, covered it, and examined whether it was alive or dead after 48 hours to determine the mortality rate (2
repetition). The results are shown in the table below.

【table】

Claims (1)

[Claims] 1 formula A pyridylpyridone derivative represented by 2 formulas An insecticide characterized by containing a pyridylpyridone derivative represented by the following as an active ingredient.