JPH0665239A - 2-acylamino-2-thiazoline compound, its production and pest control agent - Google Patents

Abstract

PURPOSE:To provide a novel compound useful as a pest control agent. CONSTITUTION:A compound of formula I (R<1> is 1-6C alkyl; R<2> is 1-8C alkyl, phenyl, 3-8C cycloalkyl; etc.; R<3> is halogen, nitro. H, 1-4C alkyl, etc.; or R<2> and R<3> form a ring together with C), e.g. 2-@9146/28}4-chloro-3-(2- chlorophenyl)-1-methyl-5-pyrazolecarbonylamino]-4,4-bis(trifluoromethy l)-5-(tetrafluoroethylidene)-2-thiazoline. The compound of formula I is obtained by reacting a 2iminothiazolidine compound of formula II with a compound of formula III (X is halogen) in the presence of a base (e.g. triethylamine) in a solvent (e.g. toluene) at room temperature to the boiling point of the solvent. The compound of formula I has insecticidal, acaricidal and germicidal effects.

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a novel 2-acylamino-2-thiazoline compound useful as a pest control agent and a method for producing the same.

[0002]

Description of the Prior Art Since the 2-acylamino-2-thiazoline compound of the present invention is a novel compound, its pest control activity is not known.

[0003]

The object of the present invention is to provide a novel 2-
It is an object of the present invention to provide an acylamino-2-thiazoline compound, a method for producing the same, and a pest control agent containing the compound as an active ingredient, which is useful as an insecticide, bactericide, acaricide or the like.

[0004]

Means for Solving the Problems As a result of research for solving the above-mentioned problems, the present inventors have found that a novel 2-acylamino-2-thiazoline compound has a remarkable controlling activity against pests. The present invention has been completed and the present invention has been completed. That is, the present invention is as follows. The first invention is
Formula (I):

[0005]

[Chemical 4]

(In the formula, R ¹ represents an alkyl group having 1 to 6 carbon atoms; R ² represents an alkyl group having 1 to 8 carbon atoms, a substituted or unsubstituted phenyl group, and a carbon atom number. 1
To four haloalkyl groups, alkylthioalkyl groups having from 2 to 5 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms; R ³ is a halogen atom, a nitro group, a hydrogen atom, C 1 -C ~ 4 alkyl groups, 1 ~ carbon atoms
Alternatively, R ² and R ³ together with the carbon atom to which they are attached can be fused to a pyrazole ring to form a 5-8 membered ring. ) Related to the 2-acylamino-2-thiazoline compound. The second invention is the following formula (II):

[0007]

[Chemical 5]

A 2-iminothiazolidine compound represented by the following formula (III):

[0009]

[Chemical 6]

(In the formula, R ¹ , R ² and R ³ have the same meanings as described in the first invention; X represents a halogen atom.)
The present invention relates to a method for producing a 2-acylamino-2-thiazoline compound represented by the above formula (I), which is characterized by reacting with a compound represented by. The third invention relates to a pest control agent containing the compound represented by the formula (I) as an active ingredient.

The present invention will be described in detail below. In the novel 2-acylamino-2-thiazoline compound [compound (I)], the starting material [compound (III) (for example, pyrazolecarboxylic acid or its reactive compound) and compound (IV)] which are the above-mentioned target compounds Shown R ¹ ,
R ² , R ³ and X are as follows.

R ¹ is a linear or branched alkyl group having 1 to 6 carbon atoms; preferably 1 to 4 is preferable; more preferably 1 to 3 (eg, ,
Methyl group, ethyl group, n-propyl group, i-propyl group, etc.) are preferred.

R ² is an alkyl group having 1 to 8 carbon atoms, a substituted or unsubstituted phenyl group, or 1 to 8 carbon atoms.
Examples thereof include four haloalkyl groups, alkylthioalkyl groups having 2 to 5 carbon atoms, and cycloalkyl groups having 3 to 8 carbon atoms.

The alkyl group for R ² is linear or branched; preferably has 1 to 6 carbon atoms, and more preferably has 1 to 4 carbon atoms. (For example, methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, t-butyl group, etc.) are preferable.

The substituent of the phenyl group in R ² is an alkyl group having 1 to 6 carbon atoms, a halogen atom, an alkoxy group having 1 to 4 carbon atoms, a haloalkyl group having 1 to 4 carbon atoms, or a carbon atom. And a haloalkoxy group having 1 to 4 atoms. And the preferable substituents are as follows.

An alkyl group having 1 to 6 carbon atoms is R ¹
(The same applies to the preferred ones and the more preferred ones. The substitution position is preferably 2 and / or
Or 4th place is good. ). The most preferred phenyl group having an alkyl group as a substituent is 2-methyl-phenyl, 4-methyl-phenyl and the like.

The halogen atom is a fluorine atom, a chlorine atom,
A bromine atom, an iodine atom and the like; preferably a fluorine atom (the substitution position thereof is preferably 2, 3, 4, 5 and / or
Or 6th place is good. ), A chlorine atom (the substitution position thereof is preferably the 2,3,4,5, and / or 6-position), and a bromine atom (the substitution position thereof is preferably the 2-position).
The most preferred phenyl group having a halogen atom as a substituent is 2-fluorophenyl, 4-fluorophenyl, 2-chloro-6-fluorophenyl, 2,6.
-Difluorophenyl, 3,4-difluorophenyl,
2,4,5-Trifluorophenyl, 2-bromophenyl, 2-chlorophenyl, 3-chlorophenyl, 3,4
-Dichlorophenyl, 2,4-dichlorophenyl, 2,
6-dichlorophenyl, 3-chloro-4-methoxyphenyl, 3,5-dichloro-2-methoxyphenyl and the like.

The alkoxy group having 1 to 4 carbon atoms is linear or branched; preferably 1 to 3 (the substitution position is preferably at the 2 and / or 4 position). .) Is good. The most preferred phenyl group having an alkoxy group as a substituent is 2-methoxy-3,5
-Dichlorophenyl, 3-chloro-4-methoxyphenyl and the like.

The halogen atom of the haloalkyl group having 1 to 4 carbon atoms is a fluorine atom, a chlorine atom, a bromine atom, an iodine atom or the like, preferably a fluorine atom is preferable; the alkyl group of the haloalkyl group is a straight chain. Although it is in the form of a ring or a branch, preferably 1 to 3 (the substitution position thereof is preferably the 2-position). And the most preferred phenyl group having a haloalkyl group as a substituent is
2-trifluoromethyl-phenyl.

The haloalkoxy group having 1 to 4 carbon atoms has the same halogen atom and alkoxy group as those described above as the halogen atom and alkoxy group of the haloalkyl group which the phenyl group has (the most preferable halogen atom is , A fluorine atom, and the most preferable alkoxy group is a methoxy group.). And the most preferred phenyl group having a haloalkoxy group as a substituent is 4-difluoromethoxyphenyl.

The haloalkyl group having 1 to 4 carbon atoms in R ² has 1 to 4 carbon atoms contained in the phenyl group.
It is the same as that shown as four haloalkyl groups. And the most preferred haloalkyl group is the trifluoromethyl group.

The alkylthioalkyl group having 2 to 5 carbon atoms in R ² is the same as the alkyl group of alkylthio and the alkyl of thioalkyl shown as the alkyl group of the phenyl group (the most preferable alkyl group is , Both are methyl groups.) And
The most preferred alkylthioalkyl group is the methylthiomethyl group.

The cycloalkyl group having 3 to 8 carbon atoms in R ² is a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group or the like; It is preferably 3 to 6; more preferably a cyclopropyl group.

R ³ is a halogen atom, a nitro group, a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or 1 to 4 carbon atoms.
Such as four alkoxy groups. The preferred ones are as follows.

The halogen atom is a fluorine atom, a chlorine atom,
It is a bromine atom, an iodine atom or the like; preferably a chlorine atom or a bromine atom.

The alkyl group may be linear or branched; preferably has 1 to 3 carbon atoms, and more preferably a methyl group.

The alkoxy group is linear or branched; preferably, it has 1 to 3 carbon atoms; and more preferably a methoxy group.

R ² and R ³ are fused to the pyrazole ring together with the carbon atom to which they are attached to give 5
To 8-membered ring, preferably 5- to 6-membered ring, more preferably 5
A member ring can be formed. In addition, the condensed ring may have a linear or branched alkyl group having 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms, and more preferably 1 to 3 carbon atoms as a substituent ( The most preferred alkyl group is
It is a methyl group. The substitution position is preferably the one described for compound 8 in Table 1. ). And the most preferable pyrazole condensed ring is the one described in the compound 4, the compound 8 and the like in Table 1.

X is a halogen atom (eg, chlorine atom,
Iodine atom, bromine atom, fluorine atom, etc.).

The compound (I) can be produced, for example, by reacting the starting compound (II) with the compound (III) in a solvent in the presence of a base, as shown below.

[0031]

[Chemical 7]

(In the formula, R ¹ , R ² , R ³ and X have the same meanings as described above.) The solvent is not particularly limited as long as it does not directly participate in this reaction, but benzene, toluene, Chlorinated or non-chlorinated aromatics, aliphatics such as xylene, methylnaphthalene, petroleum ether, ligroin, hexane, chlorobenzene, dichlorobenzene, methylene chloride, chloroform, dichloromethane, dichloroethane, trichloroethylene, cyclohexane, etc. Alicyclic hydrocarbons; ethers such as diethyl ether, tetrahydrofuran, dioxane, etc .; ketones such as acetone, methyl ethyl ketone, etc .; alcohols such as methanol, ethanol, ethylene glycol, etc., or hydrates thereof; N, N-dimethylformamide, N, N-dime Amides such as Ruasetoamido; triethylamine, pyridine, N, organic base such as N- dimethylaniline; 1,3-dimethyl -
2-imidazolidinone; dimethyl sulfoxide; a mixture of the above-mentioned solvents and the like.

The amount of the solvent used is the compound (I
The compound (II) can be used in a concentration range of 5 to 80% by weight, and preferably the compound (II) is used in a concentration of 10 to 70% by weight.

The base is an organic base [triethylamine, pyridine, 4- (N, N-dimethylamino) pyridine,
N, N-dimethylaniline, 1,8-diazabicyclo [5.4.0] undec-7-ene, etc.], alkali metal alkoxides [sodium methoxide, sodium ethoxide, etc.], inorganic bases [sodium amide, hydroxylation] Sodium, potassium hydroxide, potassium carbonate, sodium carbonate, sodium hydride, etc.] and the like.

The amount of the base used is the compound (I
It can be used in an amount of 0.001 to 5 times the molar amount of I).

The reaction temperature is not particularly limited, but is usually within the temperature range from room temperature to the boiling point of the solvent used or less.
The reaction time varies depending on the above-mentioned concentration and temperature, but is usually 0.3 to 24 hours.

The amount of the raw material compound (III) used is the compound (I
The compound (III) is 0.5 to 2 times mol, preferably 0.8 to 1.5 times mol, of I).

The compound (II) used in the present invention is, for example,
It can be produced using perfluoro- (2-methyl-2-pentene) and the like and thiourea according to the method described in JP-A-58-57371.

The compound (III) used in the present invention is, for example,
When X is a chlorine atom, as described below, J. Am.
Chem. Soc. , 70, 502 (1948)
It can be produced using pyrazolecarboxylic acids [compound (IV)] and SOCl ₂ according to the method described in the above.

[0040]

[Chemical 8]

(In the formula, R ¹ , R ² and R ³ have the same meanings as described above.) The compound (III) is substituted by each compound corresponding to the compounds 1 to 40 shown in Tables 1 to 4. Each compound (III) consisting of a type of group [compounds (III) ₁ to (III) _{40 and the} like. For example, in the compound (III) ₁ corresponding to the compound ₁ , R ¹ and R ² in the formula represented by the compound (III) are CH ₃
And R ³ is a chlorine atom and X is a halogen atom. ] Can be illustrated.

Further, in the synthesis of compound (I), in addition to the method described above, compound (III) is one of pyrazole carboxylic acids, and therefore, instead of compound (III), pyrazole carboxylic acid is separated. It can also be synthesized in the same manner as described above using a reactive derivative of (for example, acid anhydrides and esters corresponding to pyrazolecarboxylic acids).

Further, the compound (I) can also be synthesized by reacting the compound (II) with the compound (IV) in a solvent in the presence of a reaction aid such as dicyclohexylcarbodiimide. The compound (I) produced as described above is subjected to usual post-treatments such as extraction, concentration and filtration after completion of the reaction, and if necessary, known means such as recrystallization and various chromatographies. It can be appropriately purified.

Compounds (I) are compounds 1 to 40 shown in Tables 1 to 4 [for example, compound 1 is represented by the formula (I) in which R ¹ and R ² are CH ₃ and R ^{3 is} Is a chlorine atom. ] Can be illustrated.

The pests having a controlling effect with the compound (I) of the present invention are agricultural and horticultural pests [eg, Hemiptera (Plants, leafhoppers, aphids, whiteflies, etc.),
Lepidoptera (Beetle beetles, diamondback moths, leaf beetles, diamondback moths, etc.), Coleoptera (Gem beetles, weevil, beetles, chafers, etc.) Hydrangea pests (eg, flies, mosquitoes, cockroaches, etc.); stored-grain pests (bryophytes, bean weevils, etc.); root-knot nematodes in soil; pine wood nematodes; mite mite; (Rust rust, barley powdery mildew, cucumber downy mildew, rice blast, tomato plague, etc.)
And the like.

The pest control agent of the present invention is used for remarkable insecticidal
It has acaricidal and bactericidal effects and contains at least one compound (I) as an active ingredient. Compound (I)
Can be used alone, but is usually mixed with a carrier, a surfactant, a dispersant, an auxiliary agent, etc. by a conventional method (for example, powders, emulsions, fine granules, granules, wettable powders, oily preparations). (Prepared as a composition such as a suspension or an aerosol) is preferably used.

The carrier is talc, bentonite, clay,
Solid carriers such as kaolin, diatomaceous earth, white carbon, vermiculite, slaked lime, silica sand, ammonium sulfate, urea;
Hydrocarbons (kerosene, mineral oil, etc.), aromatic hydrocarbons (benzene, toluene, xylene, etc.), chlorinated hydrocarbons (chloroform, carbon tetrachloride, etc.), ethers (dioxane, tetrahydrofuran, etc.), ketones (acetone, cyclohexanone) , Isophorone), esters (ethyl acetate, ethylene glycol acetate, dibutyl maleate, etc.), alcohols (methanol, n-
Hexanol, ethylene glycol, etc.), polar solvents (dimethylformamide, dimethylsulfoxide, etc.), liquid carriers such as water; gas carriers such as air, nitrogen, carbon dioxide, and Freon (in this case, mixed injection is possible), etc. Can be illustrated.

Surfactants and dispersants that can be used to improve the performance of the present agent such as adhesion to animals and plants, improvement of absorption, dispersion of drug, emulsification and spreading are alcohol sulfates and alkyl sulfonates. , Lignin sulfonate, polyoxylene glycol ether and the like. And in order to improve the properties of the formulation,
For example, carboxymethyl cellulose, polyethylene glycol, gum arabic and the like can be used as an auxiliary agent.

The above-mentioned carrier, surfactant, dispersant and auxiliary agent can be used alone or in appropriate combination according to the purpose of use of the present agent, when producing the present agent. When the compound (I) of the present invention is formulated, the active ingredient concentration is usually 1 to 50% by weight for emulsions, 0.3 to 25% by weight for powders, and usually 1 to 90% by weight for wettable powders.
Granules are usually 0.5 to 5% by weight, and oils are usually 0.5 to 5% by weight.
5% by weight, and usually 0.1 to 5% by weight with an aerosol.

These preparations are prepared according to the purpose of use.
It can be used for various purposes by diluting it to an appropriate concentration and spraying it directly onto the water surface of plant foliage, soil, and paddy fields or applying it directly.

EXAMPLES Examples of the present invention will be specifically described below.
It should be noted that these examples do not limit the scope of the present invention. Example 1 [Synthesis of Compound (I)]

(1) 2- [4-chloro-3- (2-chlorophenyl) -1-methyl-5-pyrazolcarbonylamino] -4,4-bis (trifluoromethyl) -5-
Synthesis of (tetrafluoroethylidene) -2-thiazoline (Compound 12) 2-Imino-4,4-bis (trifluoromethyl) -5
4- (Tetrafluoroethylidene) -1,3-thiazolidine (1.1 g) and triethylamine (1 ml) were dissolved in toluene (10 ml), and 4-chloro-3- (2-chlorophenyl) which was the starting compound (III) _12. ) -1-Methyl-5-pyrazolecarboxylic acid chloride (1.0 g) was gradually added, and the mixture was stirred at room temperature for 1 hr. After the reaction, the target compound (I) was extracted from this reaction mixture with toluene, washed with water, dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The obtained oily substance was subjected to column chromatography (Wako Gel C-200, toluene: ethyl acetate = 2.
Purification by elution (0: 1) gave 0.9 g of the target compound as colorless crystals.

(2) 2- (4-Bromo-1,3-dimethyl-5-pyrazolecarbonylamino) -4,4-bis (trifluoromethyl) -5- (tetrafluoroethylidene) -2-thiazoline (compound Synthesis of 15) 2-imino-4,4-bis (trifluoromethyl) -5
4- (Tetrafluoroethylidene) -1,3-thiazolidine (1.0 g) and triethylamine (1 ml) were dissolved in toluene (10 ml), and the starting compound (III) ₁₅ , 4-bromo-1,3-dimethyl-. 5-Pyrazolecarboxylic acid chloride (0.8 g) was gradually added, and the mixture was stirred at room temperature for 1 hr. After the reaction, the target compound (I) was extracted from this reaction mixture with toluene, washed with water, dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The obtained oily substance was subjected to column chromatography (Wako Gel C-20
0, toluene: ethyl acetate = 20: 1 elution) to obtain 0.9 g of the target compound as colorless crystals.

(3) 2- [4-chloro-3- (4-fluorophenyl) -1-methyl-5-pyrazolecarbonylamino] -4,4-bis (trifluoromethyl) -5-
Synthesis of (tetrafluoroethylidene) -2-thiazoline (Compound 19) 2-Imino-4,4-bis (trifluoromethyl) -5
4- (Tetrafluoroethylidene) -1,3-thiazolidine (1.0 g) and triethylamine (1 ml) were dissolved in toluene (10 ml), and the starting compound (III) ₁₉ , 4-chloro-3- (4-fluoro). Phenyl) -1-methyl-5-pyrazolecarboxylic acid chloride (0.9 g)
Was gradually added, and the mixture was stirred at room temperature for 1 hour. After the reaction, the target compound (I) was extracted from this reaction mixture with toluene,
After washing with water and drying over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure. The obtained oily substance was subjected to column chromatography (Wakogel C-200, toluene: ethyl acetate =
Purification with 20: 1 elution gave 0.9 g of the target compound as colorless crystals.

(4) 2- (4-chloro-1-methyl-3-
Cyclopropyl-5-pyrazolecarbonylamino)-
Synthesis of 4,4-bis (trifluoromethyl) -5- (tetrafluoroethylidene) -2-thiazoline (Compound 22) 2-Imino-4,4-bis (trifluoromethyl) -5
-(Tetrafluoroethylidene) -1,3-thiazolidine (0.9 g) and triethylamine (0.8 ml) were dissolved in toluene (10 ml), and the starting compound (III) ₂₂
4-chloro-1-methyl-3-cyclopropyl-
5-Pyrazolecarboxylic acid chloride (0.6 g) was gradually added, and the mixture was stirred at room temperature for 1 hr. After the reaction, the target compound (I) was extracted from this reaction mixture with toluene, washed with water, dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The obtained oily substance was subjected to column chromatography (Wako Gel C-200, toluene: ethyl acetate = 2.
Purification by elution (0: 1) gave 1.1 g of the target compound as colorless crystals.

(5) 2- [4-chloro-3- (2-fluorophenyl) -1-methyl-5-pyrazolecarbonylamino] -4,4-bis (trifluoromethyl) -5-
Synthesis of (Tetrafluoroethylidene) -2-thiazoline (Compound 23) 2-Imino-4,4-bis (trifluoromethyl) -5
4- (Tetrafluoroethylidene) -1,3-thiazolidine (1.0 g) and triethylamine (1 ml) were dissolved in toluene (10 ml), and the starting compound (III) ₂₃ , 4-chloro-3- (2-fluoro). Phenyl) -1-methyl-5-pyrazolecarboxylic acid chloride (0.9 g)
Was gradually added, and the mixture was stirred at room temperature for 1 hour. After the reaction, the target compound (I) was extracted from this reaction mixture with toluene,
After washing with water and drying over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure. The obtained oily substance was subjected to column chromatography (Wakogel C-200, toluene: ethyl acetate =
Purification with 20: 1 elution gave 1.1 g of the target compound as colorless crystals.

(6) Synthesis of other compounds (I) in Tables 1 to 4 Other compounds (I) in Tables 1 to 4 were prepared according to the methods described in (1) to (5) above. ) Got. The compounds and their physical properties are shown in Tables 1-5.

[0057]

[Table 1]

[0058]

[Table 2]

[0059]

[Table 3]

[0060]

[Table 4]

[0061]

[Table 5]

Example 2 [Preparation of formulation] (1) Preparation of granules 5 parts by weight of compound 1, 35 parts by weight of bentonite, 57
1 part by weight of talc, 1 part by weight of Neoperex powder (trade name; manufactured by Kao Corporation) and 2 parts by weight of sodium lignin sulfonate are uniformly mixed, and then a small amount of water is added and kneaded, followed by granulation. Then, it was dried to obtain granules.

(2) Preparation of wettable powder 10 parts by weight of compound 1, 70 parts by weight of kaolin, 18 parts by weight of white carbon, 1.5 parts by weight of neoperex powder (trade name; manufactured by Kao Corporation) and 0.5 parts by weight of Demol (trade name; manufactured by Kao Co., Ltd.) was uniformly mixed and then pulverized to obtain a wettable powder.

(3) Preparation of emulsion To 20 parts by weight of compound 1 and 70 parts by weight of xylene,
0 parts by weight of toxanone (trade name; manufactured by Sanyo Kasei Co., Ltd.) was added and uniformly mixed, and dissolved to obtain an emulsion.

(4) Preparation of Dust A powder was obtained by uniformly mixing 5 parts by weight of compound 1, 50 parts by weight of talc and 45 parts by weight of kaolin.

Example 3 [Efficacy test] (1) Efficacy test against Spodoptera litura Compounds (I) shown in Tables 1 to 4 prepared according to Example 2
Each of the wettable powders of 1 is diluted to 500 ppm with water containing a surfactant (0.01%), soybean soybean leaves are dipped in each of these chemical solutions for 30 seconds, put in each plastic cup one by one, and air dried. did. In each of these cups, 10 Spodoptera litura (2nd instar larvae) were released, covered, left in a constant temperature room at 25 ° C., and after 2 days, the number of live and dead insects in each cup was counted to determine the insecticidal rate. The insecticidal effect is evaluated in four stages (A: 100%, B: 99-80%, C: 7) depending on the range of insecticidal rate.
9-60%, D: 59% or less). The following formula (V) described in JP-A-58-57371:

[0067]

[Chemical 9]

Using the comparative preparations obtained by preparing the compound (V) represented by the above in the same manner as above, the same efficacy test was examined. The results are shown in Table 6.

[0069]

[Table 6]

(2) Efficacy test against diamondback moth Compound (I) shown in Tables 1 to 4 prepared according to Example 2
Each of the wettable powders of 1 was diluted to 300 ppm with water containing a surfactant (0.01%), cabbage leaf pieces (5 cm x 5 cm) were immersed in each of these chemical solutions for 30 seconds, and one piece was placed in each plastic cup. We put each one and air dried. In each of these cups, 10 diamondback moths (third instar larvae) were released, and the cups were capped.
After leaving it in a constant temperature room at 5 ° C., the number of live and dead insects in each cup was counted 2 days later to determine the insecticidal rate. The insecticidal effect, together with the results obtained using the comparative formulation described in (1) above,
Table 7 shows the four-stage evaluation method described in (1).

[0071]

[Table 7]

(3) Efficacy test against brown planthopper Compounds (I) shown in Tables 1 to 4 prepared according to Example 2
30% of each wettable powder in water containing surfactant (0.01%)
Dilute to 0 ppm and add 30 seedlings of rice to each of these chemicals.
It was immersed for 2 seconds, air-dried, and then inserted into each glass cylinder. Next, 10 glass larvae of the 4th instar planthopper were released into each of these glass cylinders, covered with a porous cover, and allowed to stand in a constant temperature room at 25 ° C., and after 4 days, the number of live and dead insects in each glass cylinder was counted and killed. I asked for the rate. The results of the evaluation of insecticidal effect, the above (1)
The results obtained by using the comparative preparation described in (1) and the evaluation method of four stages described in (1) above are shown in Table 8.

[0073]

[Table 8]

(4) Efficacy test against adult female mites of the mite, Compounds (I) shown in Tables 1 to 4 prepared according to Example 2
30% of each wettable powder in water containing surfactant (0.01%)
Each kidney bean leaf piece (diameter: 20 m) diluted to 0 ppm and infested with 10 adult female adults
m) was immersed for 10 seconds each. Next, each leaf piece was left in a constant temperature room at 25 ° C., and three days later, the number of live and dead insects in each leaf piece was counted to determine the miticidal rate. The acaricidal effect described above
With the results obtained using the comparative formulation described in (1),
Table 9 shows the four-step evaluation method described in (1) above.

[0075]

[Table 9]

(5) Control efficacy test against barley powdery mildew (preventive effect) 10 barleys (cultivar: black wheat) were grown in a plastic flower pot with a diameter of 6 cm, and 1.5 leaf stage seedlings were grown. In addition, each of the wettable powders of the compound (I) shown in Tables 1 to 4 prepared according to Example 2 was diluted to 500 ppm with water containing a surfactant (0.01%). 20 ml of the chemical solution was sprayed per pot. These were cultivated in a glass greenhouse for 2 days, and then the barley powdery mildew fungus conidia spores were collected from the diseased leaves and sprinkled evenly over the plants to inoculate. Next, these were grown in a glass greenhouse for one week, and the degree of barley powdery mildew lesions appearing on each first leaf was investigated. The evaluation of the bactericidal effect is carried out in 6 steps (0:
The whole diseased, 1: 60% of lesion area, 2: 40% of lesion area, 3: 20% of lesion area, 4: 10% or less of lesion area, 5: No lesion) Indicated by. A similar efficacy test was examined using a comparative preparation obtained by preparing the compound (V) in the same manner as described above. The results are shown in Table 10.

[0077]

[Table 10]

(6) Control Efficacy Test Against Wheat Leaf Rust (Preventive Effect) 10 wheats (cultivar: Kobushi wheat) were cultivated in a plastic flower pot having a diameter of 6 cm, and seedlings of 1.5 leaf stage were cultivated. Each wettable powder of compound (I) shown in Tables 1 to 4 prepared according to Example 2 was treated with a surfactant (0.01
%) Was diluted to 500 ppm, and these chemicals were sprayed at 20 ml per pot. These were cultivated in a glass greenhouse for 2 days, and then a spore suspension of wheat rust (7 × 10 ⁴ spores / ml) was uniformly spray-inoculated on the plants. Next, these were grown in a glass greenhouse for one week, and the degree of wheat leaf rust lesions appearing on each first leaf was investigated. The bactericidal effect is shown in Table 11 together with the results obtained by using the comparative preparation described in (5) above, by the 6-step evaluation method described in (5) above.

[0079]

[Table 11]

[0080]

INDUSTRIAL APPLICABILITY The novel 2-acylamino-2- of the present invention
The thiazoline compound is a pesticide useful as a pest control agent.

 ─────────────────────────────────────────────────── ─── Continuation of the front page (72) Inventor Kiyoshi Tsutsumi 5 1978, Ogushi, Ube City, Yamaguchi Prefecture 5 1978, Ube Laboratory Co., Ltd. Ube Institute Co., Ltd.

Claims (3)

[Claims] 1. The following formula (I): (In the formula, R ¹ represents an alkyl group having 1 to 6 carbon atoms; R ² represents an alkyl group having 1 to 8 carbon atoms, a substituted or unsubstituted phenyl group, and 1 to 4 carbon atoms. Represents a haloalkyl group, an alkylthioalkyl group having 2 to 5 carbon atoms, and a cycloalkyl group having 3 to 8 carbon atoms;
R ³ represents a halogen atom, a nitro group, a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms; or R ² and R ³ are A 5- to 8-membered ring can be formed by condensation with a carbon atom to which it is attached to a pyrazole ring. ) 2-acylamino-2-thiazoline compound represented by the formula (1). 2. The following formula (II): 2-iminothiazolidine compound represented by the following formula (III): (Wherein R ¹ , R ² and R ³ have the same meanings as described in claim 1; X represents a halogen atom), and the compound represented by the formula (1) is reacted. Formula (I)
The manufacturing method of the compound shown by. 3. A pest control agent containing the 2-acylamino-2-thiazoline compound represented by the formula (I) according to claim 1 as an active ingredient.