JPH0489484A - Oxazoline derivative and insecticide and acaricide containing the same - Google Patents

Abstract

NEW MATERIAL:A 2,4-diphenyl-2-oxazoline derivative expressed by formula I (R<1> is H, F or Cl; Y<2> is F or Cl; X<1> is H, F, Cl, lower alkyl or lower alkoxy; X<2> to X are H, F, Cl, Br, lower alkyl or lower alkoxy; X<5> is H, F, methyl or methoxy, provided that >=3 of X<1> to X<5> will not simultaneously represent H). EXAMPLE:2-(2-Chloro-6-fluorophenyl)-4-(2-n-propoxy-4-chloro-5-bromophe nyl)-2- xazoline. USE:An insecticide and acaricide. PREPARATION:One equiv. N-(2,6- or 2-substituted phenylcarbonyl)-2-substituted phenyl-2-aminoethanol derivative expressed by formula II is allowed to react with 1-3 equiv. inorganic base (e.g. sodium hydroxide), as necessary, in a solvent at 40-100 deg.C for 20min to 2hr.

Description

DETAILED DESCRIPTION OF THE INVENTION (Field of Industrial Application) The present invention relates to a novel 2,4-diphenyl-2-oxazoline derivative and an insecticide/acaricide containing the derivative as an active ingredient.

(Prior art and problems to be solved by the invention) 2.4
- Regarding diphenyl-2-oxacillin, several reports have been made so far, mainly on production methods. For example, T e
trahedron L etters, 22 volumes,
45, pp. 4471-4474 (1981) and U.S. Pat. No. 3,440,247 describe a method for producing 2,4-diphenyl-2-oxazoline from carboxylic acid and an amino alcohol. .

On the other hand, the present inventors have proposed the following - Formation (A) [wherein Z is an oxygen atom or a sulfur atom;
Halogen atom, trifluoromethyl group or trifluoromethoxy group; Yl and Y2 may be the same or different, hydrogen atom, alkyl group, alkoxy group, alkylthio group, cyano group, nitro group, halogen atom or trifluoromethyl group ; n represents O or 1; however, when n is 0 and Xl and X2 are hydrogen atoms at the same time, or n
is l, and when Xl and X2 are any combination of substituents selected from hydrogen atoms or halogen atoms (excluding iodine atoms), Yl and Y2 are hydrogen atoms, halogen atoms (excluding iodine atoms), or It has been found that the oxa- or thiazoline derivatives represented by 1, excluding cases in which it is an arbitrary combination of substituents selected from nitro groups, are useful as insecticides and acaricides having excellent activity against aphids, mites, etc. Heading, previously proposed (Unexamined Japanese Patent Publication No. 2-85
(See Publication No. 268).

The present inventors synthesized a large number of 2,4-diphenyl-2-oxazoline derivatives in search of compounds with higher activity and/or broader physiological activities than the compound shown in Formation (A) above, We investigated their physiological activities.

(Disclosure of the Invention) As a result, we have found that a 2,4-diphenyl-oxazoline derivative having three or more substituents on the benzene ring bonded to the 4-position of the 2-oxazoline ring has a high resistance to various insects and mites. The present inventors have discovered that the present invention has insecticidal and acaricidal activity, and in particular has high insecticidal activity against Lepidoptera pests, such as leafhoppers and brown planthoppers, for which known similar compounds do not exhibit sufficient insecticidal activity.

Thus, according to the present invention, in the formula (1), Yl represents a hydrogen atom, a fluorine atom or a chlorine atom; Y2 represents a fluorine atom or a chlorine atom; X1 represents a hydrogen atom, a fluorine atom, a chlorine atom, represents a lower alkyl group or a lower alkoxy group; x2, X3 and x4 are the same or different and each represents a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, a lower alkyl group or a lower alkoxy group; 2,4-diphenyl-2-oxacillin derivatives that represent a fluorine atom, a methyl group, or a methoxy group, provided that three or more of X1 to xs do not represent hydrogen atoms at the same time; An insecticide/acaricide characterized by containing the present invention as an active ingredient is provided.

As used herein, the term "lower" means that the group or compound to which this term is attached has 6 or less carbon atoms.

Thus, a "lower alkyl group" can be linear or branched, for example methyl, ethyl, n-propyl,
Included are isopropyl, n-butyl, isobutyl, 5ec-butyl, thi-butyl, n-pentyl, impentyl, neopentyl, L-pentyl, n-hexyl, isohexyl, and the like.

In addition, "lower alkoxy group" is a lower alkyl group in which the lower alkyl moiety has the above meaning, such as methoxy, ethyne, n-propoxy, isopropoxy,
n-butquin, 5ec-butoxy, t-butoxy, n-
Examples include pentoxy and n-hexyloxy.

2,4-diphenyl-2- of the above-formation (I) of the present invention
Oxysacillin derivatives can be produced, for example, by the method shown in Reaction Formula A below.

Reaction formula A (I[) where, X1~x @1y + and Y! has the meaning given above; W
is a reactive acid residue, such as chlorine, bromine, an alkylsulfonyloxy group (e.g., methanesulfonyloxy group),
It represents an arylsulfonyloxy group (for example, p-1-luenesulfonyloquine group), etc.

In the above reaction, N-(2,6- or 2
-substituted phenylcarbonyl)-2-substituted phenyl-2-
Generally about 1 to 3 per equivalent of aminoethanol derivative
An equivalent amount of an inorganic base (e.g., sodium hydroxide, potassium hydroxide, sodium bicarbonate, potassium carbonate, sodium carbonate, etc.) is added without solvent or in a suitable solvent such as water or alcohols (e.g., methanol, ethanol, etc.). 2.4 of formula (I) by reacting at a temperature of about 40 to 100°C for about 20 minutes to 2 hours in
-diphenyl-2-oxazoline derivatives can be synthesized.

The 2,4-diphenyl-2-oxazoline derivative of formula (I) obtained by the above reaction can be purified by methods such as chromatography and recrystallization, if necessary.

Formula (It) used as starting material in the above reaction
N-(2,6- or 2-substituted phenylcarbonyl)-
The 2-substituted phenyl-2-aminoethanol derivative can be produced, for example, by the method shown in Reaction Formula B below.

Reaction formula B (nl) (IV) (V) (I[) In the formula, X1 to X', yl, y2 and W have the above meanings, and Z is a hydroxyl group or a halogen atom (preferably a chlorine atom) ) represents.

In the above reaction, 2.6- or 2 of formula (III)
- 1 mole of substituted phenylbenzoic acid or its acid halide (usually chloride) is mixed with 1 to 12 moles of the 2-substituted phenyl-2-aminoethanol derivative of formula (IV) (7) in a conventional manner, e.g. Fill (e.g., tlf,
(benzene, toluene, xylene, chloroform, carbon tetrachloride, ether, tetrahydrofuran, dioxane, etc.)
Bases (e.g. triethylamine, pyridine,
in the presence of a dehydrating agent (e.g. concentrated sulfuric acid, dicyclohexylcarbodiimide, etc.) or in an inert solvent (e.g. those mentioned above). ) at a temperature of about 0 to 200°C for about 30 minutes to 5 hours to obtain N-(2゜6-also L<is 2-substituted phenylcarbonyl)-2-substituted compound of formula (V). Phenyl-2-aminoethanol is prepared and then this compound 1 of formula (V)
About 1 to 3 moles of halogenating agent (e.g., thionyl chloride, phosphorus oxychloride, phosphorus pentachloride, phosphorus trichloride, thionyl bromide, phosphorus tribromide, etc.), or about 1 to 2 moles of alkyl A sulfonyl halide (e.g., methanesulfonyl chloride) or an arylsulfonyl halide (e.g., p-toluenesulfonyl chloride) and about 1 to 2 equivalents of a base (e.g., organic amines such as triethylamine, pyridine, etc.; sodium hydroxide, carlum hydroxide) N of formula (II) is reacted with an inorganic base such as
・(2゜6-also L< is 2-1f substituted phenylcarbonyl)
-2-substituted phenyl-2-aminoethanol derivatives can be produced. The compound of formula 1) thus obtained can be purified by methods such as chromatography and recrystallization, if necessary.

Hereinafter, the production of the compound of the present invention will be explained in more detail using synthesis examples.

Synthesis f11 2-(210rho-6-fluorophenyl)-4-(2-
n-propoxy-4-chloro-5-bromophenyl)-
Synthesis of 2-oxazoline (compound number 1) 2-(2-n-propoxy-4-chloro-5-bromophenyl)-2-aminoethanol 3.08 g (10 mmol), triethylamine 1.01 g (l 039 mol) and 50 mQ of tetrahydrofuran into the flask,
While cooling and stirring, 1.93 g (10 mmol) of 2-chloro-6-fluorobenzoylchloride was slowly added dropwise. After further stirring at room temperature for 3 hours, the generated triethylamine hydrochloride was removed using a glass filter.
The filtrate was concentrated under reduced pressure. 30 m4 of benzene and 2.38 g (20 mmol) of thionyl chloride were added to the residue, and the mixture was heated under reflux for 3 hours. After returning the reaction solution to room temperature, benzene and excess thionyl chloride were concentrated under reduced pressure, and 30 ethanol and 1.2 g (20 mmol) of potassium hydroxide were added thereto.
The mixture was heated and stirred at 70°C for 20 minutes. After the reaction was completed, the reaction solution was poured into water and extracted with ethyl acetate, and the organic layer was dried over anhydrous sodium acetate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (developing solvent: hexane:ethyl acetate = 85:15) to obtain a pale yellow liquid of 2-(2-chloro-6-fluorophenyl-4-(2-n-propoxy-4- 3.0 g of chloro-5-bromophenyl)-2-oxazoline was obtained.

vW: 1.5732 1H-NMRa:2:13ppm.

1.05 (3HS t, J-7Hz)
1.86 3680~4,36 4.76~5.16 5.50~6.00 (2H1 (3H1 (IH.

(IH.

6.86-7.90 (5H, m) IRy 2::'c+m-': 1680 (C-
N) Synthesis Example 2 2-(2,6-difluorophenyl)-4-(2-n-
Synthesis of propoxy-4,5-dichlorophenyl)-2-oxacillin (compound no. 15): n-C3H70F 2-(2-n-propoxy-4,5-dichlorophenyl)-2-amine ethanol 8-2 g (31 mmol) ,
3.13 g (31 mmol) of triethylamine and 100 n+Q of tetrahydrofuran were placed in a flask, and while cooling and stirring, 5.4 g of 2.6-cyfluoropenzoyl chloride was added.
After slowly dropping 8 g (31 mmol),
Stir for hours. The reaction solution was filtered through a glass filter to remove the generated triethylamine hydrochloride. 3.13 g (31 mmol) of triethylamine was added to the filtrate, and while cooling and stirring, 3.55 g (3.55 g) of methanesulfonyl chloride was added to the filtrate.
31 mmol) was slowly added dropwise, and the mixture was further stirred at room temperature for 2 hours. After removing triethylamine hydrochloride produced from the reaction solution using a glass filter, the solvent was concentrated under reduced pressure. 80 ml of methanol was added to the residue, and further 3.5 g (62 mmol) of potassium hydroxide was added and the mixture was heated and stirred for 1 hour. After the reaction was completed, the reaction solution was poured into water, extracted with ethyl acetate, and the organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (developing solvent: hexane:ethyl acetate-9=1) to obtain 2-(2,6-difluorophenyl)-4- as a pale yellow solid.
(2-n-propoxy-4,5-dichlorophenyl)-
5.1 g of 2-year-old xacillin was obtained.

mp: 82-85℃'H-N M Ra rT,'',''ppm: 1.05
(3H, tll, 86
(2H1 3,96 (IH.

4.13 (IH.

4.90 (IH.

5.33 (IH.

J=7Hz) J=7Hz) J-7Hz) J-9Hz) J=9Hz) J=9Hz) 6.83-7.76 (5H% m)IRp 2:"
, 'cm-': 1 6 8 8 (C=N)
Synthesis Example 3 2-(2,6-difluorophenyl)-1methoxy4-methyl-5-chlorophenyl)-2-
Synthesis of Oxazoline (Compound No. 31) 2-(2-methoxy-4-methyl-5-chlorophenyl)-2-aminoethanol 2.16 g (10 mmol), triethylamine 1.01 g (10 mmol) and tetrahydro7rane 30+o ( + in a flask, cooled and stirred, 2.6
-1.77 g (10 mmol) of cyfluoropenzoyl chloride was added dropwise. After further stirring at room temperature for 3 hours, the produced triethylamine hydrochloride was removed with a glass filter, and the filtrate was concentrated under reduced pressure. This concentrate contains 30% benzene.
m12 and 3.57 g (30 mmol) of thionyl chloride were added, and the mixture was refluxed for 2 hours on an oil bath while stirring.

After the reaction solution was returned to room temperature, it was concentrated under reduced pressure. To the residue, add 30 mff of methanol and 4 m of 30% aqueous sodium hydroxide solution (
1 was added and stirred at 70°C for 20 minutes.

After the reaction was completed, the reaction solution was poured into water and extracted with ethyl acetate.
The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure.

The concentrate was purified by silica gel column chromatography (developing solvent: n-hexane:ethyl acetate = 8:2) to obtain 2-(2゜6-difluorophenyl)-4- as a pale yellow solid.
(2-methoxy-4-methyl-5-chlorophenyl)-
2.4 g of 2-oxazoline was obtained.

mp: 104-106℃' H-N M Ra:,”,”ppm:2.37
(3H,s)3.82
(3H.

4.11 (IH.

4.87 (IH.

5.64 (IH.

S) tX J-9Hz) t, J-9Hz) dd, J-9Hz.

1Hz) 6.75-7.70 (5H% m) I Ru 2:", 'cm-': 1 6 5 6 (C=N)
Example 4 2-C2-chloro-6-fluorophenyl)4-(2-
methoxy-3-chloro-4,6-dimethylphenyl)-
Synthesis of 2-oxazoline (compound number 64) 2-(2-methoxy-3-chloro-4,6-dimethylphenyl)-2-aminoethanol 2.30 g (10 mmol), triethylamine 1.01 g (10 mmol)
and 30+aQ of tetrahydrofuran into 7 flasks,
2-chloro-6-fluorobenzoyl chloride 1.9
3 g (10 mmol) was added over 30 minutes under ice-cooling and stirring. After further stirring at room temperature for 3 hours, the produced triethylamine hydrochloride was removed with a glass filter, and the filtrate was concentrated under reduced pressure. 30 J of benzene and 3.57 g (30 mmol) of thionyl chloride were added to this concentrate, and the mixture was refluxed on an oil bath for 2 hours while stirring. After the reaction solution was returned to room temperature, it was concentrated under reduced pressure. 30 mL of methanol and 4 mQ of 30% aqueous sodium hydroxide solution were added to the residue, and the mixture was stirred at 70°C for 20 minutes. The mixture was dissolved in 100 mQ of ethyl acetate, washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. To this concentrate, 30 ml of methanol was added, followed by 4 mQ of 30% aqueous sodium hydroxide solution, and the mixture was stirred at 70° C. for 20 minutes. After the reaction was completed, the reaction solution was poured into water, extracted with ethyl acetate, and the organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure.

The residue was subjected to silica gel column chromatography (development; n
- Hexane:ethyl acetate = 7:3) to give a pale yellow viscous oil, 2-(2-chloro-6-fluorophenyl)-4-(2-methoxy-3-chloro-4,6-dimethylphenyl). )-2-oxazoline (2.5 g) was obtained.

1.5826 'H-NMRaCD'ppm: 2.33 (3H% S) 2.50
(3H, s) 3.77 (3H, s) 4.27~4.87 (2H, m) 5.97 (IH,, t, J = 9
Hz) 6.80-7.53 (3H, Il+)I
Rν 2::Icm-': I 6 8 0 (
C-N) Synthesis Example 5 2-(2,6-difluorophenyl)-4-(2,3,
5,6-tetrafluoro-4-n-butoxyphenyl)
Synthesis of -2-oxazoline (Compound No. 72) 2-(2,3,5,6-tetrafluoro-4-〇-pxiphenyl)-2-amineethanol 2.81 g (1
0 mmol), 1.01 g (10 mmol) of triethylamine, and 30 mA of tetrahydrofuran were placed in a flask, and 1.77 g (10 mmol) of 2,6-cyfluoropenzoyl chloride was added dropwise while stirring while cooling. After further stirring at room temperature for 3 hours, the produced triethylamine hydrochloride was removed with a glass filter, and the filtrate was concentrated under reduced pressure.

In this concentrate, benzene 30 mα, thionyl chloride 3.57
g (30 mmol) and refluxed on an oil bath for 2 hours while stirring.

30 rn (A) of methanol and 4 mQ of 30% aqueous sodium hydroxide solution were added to the residue, and the mixture was stirred at 70°C for 20 minutes.

After the reaction was completed, the reaction solution was poured into water and extracted with ethyl acetate.
The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure.

The residue was purified by silica gel column chromatography (developing solvent: n-hexane:ethyl acetate-7:3) to obtain 2-(2,6-difluorophenyl)- as a pale yellow viscous oil.
4-(2,3°5.6-tetrafluoro-4-n-butoxyphenyl)-2-oxazoline 2.1 was obtained.

Ma B: 1.5132 'H-NMRJTM,' ppm: 0.77-1.13 (3HSm) 1.20-2.00 (4H, m) 4.90 (IH% t, J-9Hz)5. 70
(IH, t, J=9Hz) 6.83-7.80
(3H%m) I Ry 2::'am-': I 6 7 0
(C=N) Compounds shown in Table 1 below were synthesized in the same manner as in Synthesis Examples 1 to 5 above. Note that Table 1 also lists the compounds obtained in Synthesis Examples 1 to 5.

However, the physical property values in the table represent refractive index (vB) or melting point (° C.). In addition, the abbreviations in the table have the following meanings. Table 1 Compounds of formula CI) provided by the present invention exhibit strong ovicidal, insecticidal, and acaricidal activities against insects and mites that are harmful to agriculture and horticulture, as evidenced by the test examples described below. Moreover, it has little phytotoxicity to useful crops, and is useful as an active ingredient in insecticides and acaricides for concentrated horticulture.

Therefore, the compound of formula (I) of the present invention can be used against insects and mites that damage useful crops, such as the green peach aphid (Myzus persicae), the cotton aphid (A phisgossypii), and the white radish aphid (L 1paphis pseudobr).
assicae), Citrus aphid (Aph
Aphids such as N. is citricola and N.
ttix cincticeps)
s), white-legged planthopper (S ogatellafurc)
ifera), brown planthopper (N i Iaparv)
planthoppers such as ata (concave and concave); leafhoppers; diamondback moth (p.
jutella xylostella) S. podopteralitura, Chilosuppressal iS
) and other Lymphoptera pests, such as the two-spotted spider mite (T etranyc
hus urticae), false red spider mite (T.
etranychus cinnabarinus)
, T etranychuskanz
awai), apple spider mite (P anonychus)
ulmuri, orange spider mite (P anonychus)
It exhibits excellent control effects against spider mites such as P. citri.

Therefore, according to the present invention, an agricultural and horticultural insecticide containing the compound of formula (I) as an active ingredient.
Acaricides are provided.

When the compound of the present invention is actually used as an active ingredient of an insecticide/acaricide, one or two of the compounds of formula (1) are used.
Although seeds or more may be used as they are, they can usually be formulated into various forms together with agriculturally and horticulturally acceptable auxiliaries.

Examples of auxiliary agents that can be used in formulation include carriers, diluents, surfactants, dispersants, fixing agents, stabilizers, etc., and can be appropriately selected and added as necessary depending on the dosage form.

Carriers or diluents include solid and liquid carriers or diluents. Examples of solid carriers or diluents include mineral powders or granules such as diatomaceous earth, talc, clay, alumina, kaolin, montmorinite, silicic acid, and white carbon; animal and vegetable powders such as starch, soybean flour, wheat flour, and fish meal; Liquid carriers or diluents include, for example, water, alcohols (e.g. methanol, ethylene glycol, phenoquine ethanol, etc.), ketones (e.g. acetone, methyl ethyl ketone, etc.), aromatic hydrocarbons (e.g. xylene, trimethylbenzene, methylnaphthalene, solvent naphtha, etc.), aliphatic hydrocarbons (e.g. hexane, cyclohexane, kerosene, kerosene, etc.), ethers (e.g. dioxane, diisopropyl ether, tetrahydro7rane, etc.), halogenated hydrocarbons (e.g. Examples include dichloromethane, trichloroethane, etc.), acid amides such as dimethylformamide, esters such as ethyl acetate, nitriles such as acetonitrile, sulfur-containing compounds such as dimethyl sulfoxide, and vegetable oils such as soybean oil and olive oil.

Examples of the surfactant include nonionic polyoxyalkylene alkyl ether, polyoxyalkylene alkyl allyl ether, polyoxyalkylene fatty acid ester, polyoxyalkylene sorbitan fatty acid ester, anionic alkyl allyl sulfate salt, polyoxy Examples include alkylenealkylaryl sulfate salts, and mixtures thereof.

Examples of the dispersant and fixing agent include lignin sulfonate, alkylbenzene sulfonate, naphthalene sulfonic acid formalin condensate, alginate, starch, cellulose derivative, montmorillonite, synthetic water-soluble polymer, and synthetic resin.

As stabilizers, phosphate esters, glycols,
Examples include nonionic surfactants, aromatic diamic acids, vegetable oils, and epoxidized oils.

Furthermore, the preparation containing the compound of formula (1) of the present invention can be mixed or used in combination with other agricultural chemicals, such as insecticides, acaricides, fungicides, etc., as necessary, thereby providing a layer of It may also show excellent effects.

Insecticides or acaricides that can be mixed or used in combination include, for example, fenitrothion, diazinon, fenthion, chlorpyrifos, salithion, malathion, acephate, trichlorfon, dichlorpos, pyridafention, carbaryl, profoxur, fenopucarb, fenvalerate, permethrin, cyfluthrin, fluparinate, Cycloprothrin, etofenbrox, diflubenzuron, chloro7luazuron, fuflo7edzin,
Compounds such as hexythiazox, fenbutastin oxide, dicofol, and bensultap are mentioned, and the fungicides include, for example, ibrobenfos, nidifenphos, dione, polycarbamate, bitertanol, triadimefon, dithianone, thiophanate methyl, benomyl, fluorimide, procymidone, and isoprodione. , cabtan, difortan, polyoxin, and other compounds.

The compound of formula (I) of the present invention can be prepared into preparations such as irrigation agents, granules, powders, emulsions, flowables, microcapsules, etc. using the above-mentioned ingredients and according to methods known per se to formulate agrochemical formulations. It can be formulated into molds. The blending ratio of the active compound of formula (1) in these preparations can be varied over a wide range depending on the type of compound, dosage form, etc., but for boat fishing, the content of the compound is 0.01 to 80% by weight. %, and more preferably, depending on the individual dosage form, for example, in the case of emulsions, aqueous preparations, flowable preparations, etc., the compound of formula (I) is 0.01 to 50% by weight,
More preferably, it can be contained in a concentration of 0.1 to 20% by weight, and in the case of powders and granules, the compound of formula (1) can be contained in a concentration of 0.01 to 20% by weight, more preferably 0.01 to 20% by weight. 1
It can be included at a concentration of ~10% by weight.

The preparations containing the compound of formula (I) according to the invention can be applied directly to the adults, larvae or eggs of insects or mites harmful to agricultural and horticultural crops, or applied to the areas where the adults, larvae or eggs live. By spraying the active ingredient (I), it can be used to control harmful insects and/or mites. The amount of the compound of formula (I) to be applied at this time can be changed appropriately depending on the type of active compound, dosage form, pest outbreak situation, etc., but it is generally 1 to 10,000 g per hectare.
1, preferably within the range of 10 to 1.000 g, and more specifically, for example, in the case of the above-mentioned emulsions, wettable powders, and 70% ablative agents, they are usually 1,000 g.
~10,000 times diluted, 1,000 per hectare
0-10. In the case of powders and granules, it is usually appropriate to apply them at a rate of 2 to 40 kg per hectare.

Examples of formulations of the compound of formula (I) of the present invention will be described below, but the scope of the present invention is not limited thereto.

In the examples below, all "parts by weight" are parts by weight.

Formulation Example 1 (Emulsion) 80 parts of xylene is added to 10 parts of the compound of the present invention (Compound No. 1), 5 parts of alkylaryl sulfonate, and 5 parts of polyoxyalkylene alkyl allyl ether, and the mixture is uniformly dissolved to form an emulsion.

Formulation Example 2 (Wettable powder) 10 parts of the compound of the present invention (Compound No. 19), 5 parts of polyoxyalkylene alkylaryl sulfate, 5 parts of lignin sulfonate, and ±80 parts of diatom were mixed and ground to form a wettable powder. do.

Formulation Example 3 (Powder) 1 part of the compound of the present invention (compound number 30), 1 part of white carbon, and 98 parts of fine clay are mixed and ground to obtain a powder.

Formulation Example 4 (Granules) After uniformly mixing 5 parts of the compound of the present invention (compound number 43), 5 parts of lignin sulfonate, 45 parts of bentonite, and 45 parts of clay, an appropriate amount of water was added and kneaded to form granules. The mixture is granulated using a machine and dried through ventilation using a fluidized fluid dryer to form granules.

Formulation Example 5 (Flowable) After uniformly stirring and dispersing 10 parts of the compound of the present invention (Compound No. 62), 5 parts of polyvinyl alcohol, 5 parts of polyoxyalkylene alkyl allyl ether, 5 parts of ethylene glycol, and 74.9 parts of water, 0 parts of xanthan gum was added. .1 part is added and mixed to make a flowable.

Next, test examples will be given to demonstrate the excellent insecticidal and acaricidal effects of the compound of formula (I) of the present invention.

Test Example 1 (Ovicidal test for two-spotted spider mites) Fill an ice cream container (diameter 9 am) with water, make a hole in part of the lid, and leave the entire filter paper absorbing water and becoming damp.
I put green bean leaves on top. Female adult two-spotted spider mite on leaves 1
After inoculating 0 larvae and allowing them to lay eggs for 24 hours, the female adults were removed. Spray the drug at a predetermined concentration (emulsion of Formulation Example 1 diluted with water), leave to stand in a constant temperature room (25°C), and after 7 days, investigate the number of snoring larvae under a microscope to determine the ovicidal rate. Ta. The test was conducted in three consecutive sections. The results are shown in Table 2 below.

Table 2 Test Example 2 (Insecticidal test against peach aphid nymphs) Radish seedlings at the two-leaf stage planted in cups were infested with 5 electrolipidous female adults per seedling, and allowed to lay eggs for 3 days. Adult insects were removed and a prescribed concentration of drug (emulsion of Formulation Example 1 diluted with water) was sprayed. The treated bacteria were placed in a greenhouse, and the insect mortality rate was determined after 96 hours. The test was conducted in three consecutive sections. The results are shown in Table 3 below.

Table 3 Table 4 Test Example 3 (Insecticidal test against leafhopper larvae) Rice seedlings planted in a cup were sprayed with a prescribed concentration of chemical (wettable powder of Formulation Example 2 diluted with water), and after air-drying, an acrylic rice seedling was sprayed. A cylinder was placed over the tube, 10 leafhopper larvae were released per seedling, and the tube was covered with gauze. The treated surface was placed in a greenhouse, and the mortality rate was investigated after 7 days to determine the insecticidal rate. The test was conducted in three consecutive sections. The results are shown in Table 4 below.

※※Compound No. 74 described in JP-A-2-85268
Compound test example 4 (insecticidal test against brown planthopper larvae) Spray a prescribed concentration of the chemical (diluting agent of formulation example 2 with water) on rice seedlings planted in a cup, and after air-drying, cover with an acrylic cylinder and test against brown planthopper larvae. Release 10 larvae per seedling,
I covered it with gauze. The treated bacteria were placed in a greenhouse, and the insect mortality rate was determined after 7 days. The test was conducted in three consecutive sections. The results are shown in Table 5 below.

Table 5 ※Compound No. 74 described in JP-A-2-85268
Compound Test Example 5 (insecticidal test against diamondback moth larvae) A cabbage leaf piece (2 cm square) was immersed in a chemical solution of a predetermined concentration (emulsion of Formulation Example 1 diluted with water), and after air-drying, it was placed in an ice cream cup with a diameter of 9 cm. Placed together with 15 snoring larvae at 25°C.
The insecticide rate was investigated after 3 days. The test was conducted in two consecutive sections. The results are shown in Table 6 below.

Table 6

Claims (2)

[Claims] (1) General formula (I) ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (I) In the formula, Y^1 represents a hydrogen atom, a fluorine atom, or a chlorine atom; Y^2 represents a fluorine atom or a chlorine atom ; X_1 represents a hydrogen atom, a fluorine atom, a chlorine atom, a lower alkyl group, or a lower alkoxy group; Represents an atom, a lower alkyl group, or a lower alkoxy group; X^5 represents a hydrogen atom, a fluorine atom, a methyl group, or a methoxy group, provided that three or more of X^1 to X^5 simultaneously represent a hydrogen atom A 2,4-diphenyl-2-oxazoline derivative represented by: (2) An insecticide/acaricide containing the 2,4-diphenyl-2-oxazoline derivative of the general formula (I) according to claim 1 as an active ingredient.