JP2002338551A - 2-anilino-4 (3H) -pyrimidinone derivatives and production intermediates, their production methods, and pesticidal agents containing them as active ingredients - Google Patents

Abstract

(57) [Problem] To provide a pesticidal agent having an extremely excellent controlling effect on harmful phytopathogenic fungi, insects, mites and weeds in various agricultural and horticultural activities. SOLUTION: General formula (1) 2-anilino-4 (3H) -pyrimidinone derivatives represented by the formula: and pesticides containing them as active ingredients.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

TECHNICAL FIELD The present invention relates to a novel 2-anilino-4 (3H) -pyrimidinone derivative, an intermediate for producing the same, a method for producing them, and a pesticidal agent containing them as an active ingredient, in particular, The present invention relates to an insecticide, acaricide, fungicide, and herbicide effective for controlling pests for agricultural and horticultural use.

[0002]

2. Description of the Related Art Conventionally, in the agricultural and horticultural field, various insecticides for controlling various pests have been developed and put to practical use. However, conventionally used agricultural and horticultural insecticides are not always satisfactory in terms of insecticidal effect, insecticidal spectrum, residual efficacy, and the like. Further, it cannot be said that the requirements such as reduction of the number of times of application and the amount of applied medicine are satisfied.

[0003] In addition, the appearance of pests that have acquired resistance to conventional agricultural chemicals has also become a problem. For example, vegetables,
In the cultivation of fruit trees, flowers, tea, wheat, rice, etc., various types of pesticides, for example, triazole, imidazole, pyrimidine, benzimidazole, dicarboxyimide, phenylamide, organophosphorus, etc. Various pests that have acquired resistance have emerged in various places, and it has become difficult to control these pests year by year.

There are pesticides to which pests have not yet acquired resistance (for example, dithiocarbamate-based and phthalimide-based pesticides), but these are generally large in the amount and frequency of application, and are preferable from the viewpoint of environmental pollution and the like. is not. Therefore, there is a strong need for the development of a novel insecticide that shows a sufficient control effect at a low dose even for various pests that have acquired resistance to conventional general-purpose agricultural and horticultural insecticides, and that has little adverse effect on the environment. I have. As for the acaricide, the development of a highly safe acaricide is also expected, which shows an excellent control effect on mites that have been resistant to conventional general-purpose acaricides.

On the other hand, WO93 / 21162 (Japanese Unexamined Patent Publication No.
No. 321913) discloses a 2-anilinopyrimidin-4-one derivative having herbicidal activity and action of a plant growth regulator. However, the above publication does not disclose any physiological activity other than the herbicidal activity and the activity as a plant growth regulator of these compounds, such as insecticidal and acaricidal activities. In addition, WO98 / 5115
2, WO98 / 51675, WO99 / 52881 and WO00 / 29387 disclose 2-anilinopyrimidin-4-one derivatives having insecticidal and acaricidal activity, which are described in these publications. Anilinopyrimidin-4-one derivatives are not always satisfactory in terms of activity and toxicity.

[0006]

SUMMARY OF THE INVENTION An object of the present invention is to provide a high control effect on conventional agricultural and horticultural fungicides and various pests which are resistant to insecticides and acaricides, and also to provide a high level of safety for crops. An object of the present invention is to provide a novel pesticidal agent having both good germ resistance and excellent herbicidal activity against weeds.

[0007]

The present inventors have conducted intensive studies to solve the above-mentioned problems, and as a result, have found a novel 2-anilino-4 (3H) -pyrimidinone represented by the following general formula (1). The inventors have found that the derivative is a compound having the above characteristics, and have completed the present invention.

That is, the present invention provides a compound represented by the general formula (1):

[0009]

Embedded image

In the formula, R ¹ represents a halogen atom, a C ₁ -C ₄ alkyl group, a C ₁ -C ₄ haloalkyl group or an optionally substituted phenyl group, and R ² represents a hydrogen atom or a halogen atom . R ³ is a C ₁ -C ₆ alkyl group, a C ₁ -C ₆ haloalkyl group, a (C ₁ -C ₆ alkoxy) C ₁ -C ₆ alkyl group, a C ₃ -C ₆ alkenyl group, a C ₃ -C ₆ haloalkenyl group, C ₃ -C ₆ alkynyl group, C ₃ -C ₆ haloalkynyl group, C ₃ -C ₈ cycloalkyl group, which may be a aralkyl group, or a substituted or optionally substituted C ₂ -C ₆ vinyl groups Represents R ⁴ is a general formula (2)

[0011]

Embedded image

(Where R^FiveAnd R⁶Are each independently C₁
~ C₆Alkyl group or C_Three~ C₈A cycloalkyl group represented by n
Represents an integer of 0 to 5. ) Represents a substituent.
X represents a hydrogen atom, a halogen atom, C₁~ C_FourAlkyl group, C
₁~ C_FourHaloalkyl group, C_Three~ C₆Alkenyl group, C_Three~
C₆Alkynyl group, C₁~ C_FiveAcyl group, carboxy group,
(C ₁~ C_FourAlkoxy) carbonyl group, cyano group, hydrido
Roxy group, C₁~ C_FourAlkoxy group, C₁~ C_FourHalo alco
A xy group, (C₁~ C_FourAlkoxy) C₁~ C_FourAlkoxy
Group, carboxy (C₁~ C_FourAlkoxy) group, (C₁~ C_Four
Alkoxy) carbonyl (C₁~ C_FourAlkoxy) group, C
_Three~ C₆Alkenyloxy group, C_Three~ C₆Alkynyloxy
Group, an optionally substituted phenyloxy group, C₁~ C_Five
Acyloxy group, mercapto group, C₁~ C_FourAlkylthio
Group, C₁~ C_FourHaloalkylthio group, C₁~ C_FourAlkyls
Rufinyl group, C₁~ C_FourHaloalkylsulfinyl group,
C₁~ C_FourAlkylsulfonyl group, C₁~ C_FourHaloalkyl
Sulfonyl group, amino group, C₁~ C_FourAlkylamino group,
J (C₁~ C_FourAlkyl) amino group, C₁~ C_FiveAcylami
No group, C₁~ C_FourAlkylsulfonylamino group or nitro
M represents an integer of 1 to 5; Where m is 2
In the case of integers from to 5, X may be the same or different. }so
2-anilino-4 (3H) -pyrimidinone derivatives shown
Body and pest control containing these as active ingredients
Insecticides, acaricides, fungicides and herbicides
Things.

Further, the present invention provides a compound represented by the following general formula (3):

[0014]

Embedded image

(Wherein R ¹ , R ² , R ³ , X and m represent the same meaning as described above).
H) -pyrimidinone derivatives and a compound of the general formula (4)

[0016]

Embedded image

(Wherein, R ⁴ has the same meaning as described above;
Represents a leaving group. Wherein the reagent represented by the formula (1) is reacted in the presence of a base.

[0018]

Embedded image

(Wherein, R ¹ , R ² , R ³ , R ⁴ , X and m have the same meanings as described above)
The present invention relates to a method for producing a (3H) -pyrimidinone derivative.

[0020]

BEST MODE FOR CARRYING OUT THE INVENTION The 2-anilino-4 (3
In the H) -pyrimidinone derivative, R ¹ is a halogen atom such as a fluorine atom, a chlorine atom, a bromine atom or the like; a C ₁ -C ₄ alkyl such as a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group or an isobutyl group. Groups: fluoromethyl group, chloromethyl group, bromomethyl group, trichloromethyl group, trifluoromethyl group, 1-chloroethyl group, 2-chloroethyl group, 2,2,2-trifluoroethyl group, pentafluoroethyl group, 3- C ₁ -C ₄ haloalkyl groups such as chloropropyl group; a halogen atom, C ₁ ~
Examples include a phenyl group which may be substituted with a C ₄ alkyl group or a C ₁ -C ₄ haloalkyl group, and preferably a trifluoromethyl group, a pentafluoroethyl group or a trichloromethyl group. .

Examples of R ² include a hydrogen atom; a halogen atom such as a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.
Examples include a chlorine atom and a bromine atom.

R ³ is methyl, ethyl, propyl, isopropyl, butyl, isobutyl, s
ec-butyl group, tert-butyl group, cyclopropylmethyl group, pentyl group, isopentyl group, neopentyl group, hexyl group, isohexyl group and other C ₁ -C ₆ alkyl groups; fluoromethyl group, chloromethyl group, bromomethyl group, Trichloromethyl group, trifluoromethyl group, 1-
Chloroethyl group, 2-chloroethyl group, 2-bromoethyl group, 2-chloropropyl group, 2-bromopropyl group,
A C ₁ -C ₆ haloalkyl group such as a 1-chloro-2-propyl group, a 1-bromo-2-propyl group, a 3-chloropropyl group, a 3-fluoropropyl group; a methoxymethyl group;
A (C ₁ -C ₆ alkoxy) C ₁ -C ₆ alkyl group such as a methoxyethyl group, an ethoxymethyl group and a 2-ethoxyethyl group; a 2-propenyl group, a 2-methyl-2-propenyl group, a 2-butenyl group, 3-methyl-2-butenyl group, 1
A C ₃ -C ₆ alkenyl group such as -buten-3-yl group;
Propargyl; chloro-2-propenyl group, 3-chloro-2-propenyl C ₃ -C ₆ haloalkenyl group such as
2-butynyl group, C ₃ and 1-butyn-3-yl group -C ₆
Alkynyl group; C ₃ such as 3-bromo-2-propynyl group
-C ₆ haloalkynyl group; cyclopropyl group, a cyclopentyl group, 3-methylcyclopentyl group, C ₃ -C ₈ cycloalkyl groups such as cyclohexyl group; a benzyl group, 2-
Chlorobenzyl group, 3-chlorobenzyl group, 4-chlorobenzyl group, 2-fluorobenzyl group, 3-fluorobenzyl group, 4-fluorobenzyl group, 2,4-dichlorobenzyl group, 3,5-dichlorobenzyl group, 2,4-difluorobenzyl group, 3,5-difluorobenzyl group,
2-methylbenzyl group, 3-methylbenzyl group, 4-methylbenzyl group, 4-isopropylbenzyl group, 4-isobutylbenzyl group, 4-trifluoromethylbenzyl group, 4-methoxybenzyl group, 3,4-dimethoxybenzyl Group, 1-phenylethyl group, 1-methyl-1-phenylethyl group, 2-phenylethyl group, 1-methyl-2
An optionally substituted aralkyl group such as -phenylethyl group, 3-phenylpropyl group, 4-phenylbutyl group, 4-phenyloxybenzyl group; vinyl group, 1-propenyl group, 1-propen-2-yl group , 1-butenyl group, 1-buten-2-yl group, 2-buten-2-yl group, 3-methyl-1-butenyl group, optionally substituted, such as 1-pentenyl group C ₂ -C ₆ A vinyl group can be exemplified.

R ⁵ and R ⁶ are methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, cyclopropylmethyl, pentyl, isopentyl, C ₁ -C ₆ such as neopentyl, hexyl, isohexyl, etc.
Alkyl group or cyclopropyl group, cyclopentyl group,
It can be mentioned C ₃ -C ₈ cycloalkyl groups such as cyclohexyl group.

X represents a hydrogen atom; a halogen atom such as a fluorine atom, a chlorine atom, a bromine atom and an iodine atom; a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group and a tert. - C ₁ -C ₄ alkyl group such as butyl group; fluoromethyl group, chloromethyl group, bromomethyl group, trichloromethyl group, trifluoromethyl group, 1-chloroethyl group, 2-chloroethyl group, such as 3-chloropropyl group C ₁ -C ₄ haloalkyl group; a 2-propenyl group, 3-methyl-2-propenyl, 2-butenyl, 3-methyl-2-butenyl group,
1-buten-3-yl C ₃ -C ₆ alkenyl group such as a group; propargyl, 2-butynyl group, 1-butyn-3-yl C ₃ -C ₆ alkynyl group such as a group; a formyl group, an acetyl group, A C ₁ -C ₅ acyl group such as a propionyl group, a butyryl group, a valeryl group, a pivaloyl group; a carboxy group; a methoxycarbonyl group, an ethoxycarbonyl group, a propoxycarbonyl group, an isopropoxycarbonyl group, a butoxycarbonyl group, an isobutoxycarbonyl group, (C ₁ -C ₄ alkoxy) carbonyl groups such as sec-butoxycarbonyl group and tert-butoxycarbonyl group; cyano group; hydroxy group; methoxy group, ethoxy group, propoxy group, isopropoxy group, butoxy group, isobutoxy group, sec.
C ₁ -C ₄ alkoxy groups such as -butoxy group and tert-butoxy group; trifluoromethoxy group, difluoromethoxy group, 2-chloroethoxy group, 3-chloropropoxy group, 2-chloro-1-methylethoxy group, 2 , 2, 2-
A C ₁ -C ₄ haloalkoxy group such as a trifluoroethoxy group; a (C) group such as a methoxymethoxy group, an ethoxymethoxy group, an isopropoxymethoxy group, a 2-methoxyethoxy group;
₁ -C ₄ alkoxy) C ₁ -C ₄ alkoxy group; carboxymethoxy group, 1- (carboxy) carboxy, such as an ethoxy group (C ₁ -C ₄ alkoxy) group; a methoxycarbonyl methoxy group, an ethoxy carbonyl methoxy group, 1- A (C ₁ -C ₄ alkoxy) carbonyl (C ₁ -C ₄ alkoxy) group such as a (methoxycarbonyl) ethoxy group; a 2-propenyloxy group, a 2-methyl-2-propenyloxy group,
2-butenyloxy, 3-methyl-2-butenyloxy group, 1-buten-3-yloxy C ₃ -C ₆ alkenyloxy group such group; a 2-propynyl group, 1-methyl-2-propynyloxy group, 2 A C ₃ -C ₆ alkynyloxy group such as a butynyloxy group; a phenyloxy group,
An optionally substituted phenyloxy group such as a phenyloxy group such as a methylphenyloxy group, a 3-chlorophenyloxy group, a 2-fluorophenyloxy group or a 4-fluorophenyloxy group; a C group such as an acetoxy group or a propionyloxy group; ₁ -C ₅ acyloxy group; a mercapto group;
Methylthio, ethylthio, propylthio, isopropylthio, butylthio, isobutylthio, se
C _1- such as a c-butylthio group and a tert-butylthio group;
C ₄ alkylthio groups; chloromethyl thio group, difluoromethylthio group, trifluoromethylthio group, trichloromethylthio _{group, 2, 2, C 1 ~C} 4 haloalkylthio groups such as 2-trifluoroethyl thio group; methylsulfinyl group, ethylsulfinyl Group, propylsulfinyl group,
Isopropylsulfinyl group, butylsulfinyl group,
Chloromethyl methylsulfinyl group; isobutyl sulfinyl group, sec- butyl sulfinyl group, tert- butyl sulfinyl C ₁ -C ₄ alkylsulfinyl group such as Le group
Difluoromethylsulfinyl group, trifluoromethylsulfinyl group, trichloromethylsulfinyl group,
C such as 2,2,2-trifluoroethylsulfinyl group
₁ -C ₄ haloalkylsulfinyl group, methylsulfonyl group, ethylsulfonyl group, propylsulfonyl group, isopropylsulfonyl group, butylsulfonyl group, iso-butylsulfonyl group, sec- butylsulfonyl group, ter
C ₁ -C ₄ alkylsulfonyl groups such as t-butylsulfonyl group; chloromethylsulfonyl group, difluoromethylsulfonyl group, trifluoromethylsulfonyl group, trichloromethylsulfonyl group, 2,2,2-trifluoroethylsulfonyl group and the like C ₁ -C ₄ haloalkylsulfonyl group, an amino group, methylamino group, ethylamino group, propylamino group, isopropylamino group, C ₁ -C ₄ alkylamino groups such as butylamino group; a dimethylamino group, diethylamino group, methyl Di (C ₁₎ such as propylamino group
-C ₄ alkyl) amino group; methylsulfonylamino, C ₁ -C ₄ alkylsulfonylamino groups such as ethylsulfonylamino group; formylamino group, acetylamino group, C ₁ -C ₅ acylamino group such as a propionylamino group;
A nitro group and the like can be exemplified.

The leaving group represented by L includes a chlorine atom,
Examples thereof include a halogen atom such as a bromine atom and an iodine atom, and a substituted sulfonyloxy group such as a methylsulfonyloxy group, a trifluoromethylsulfonyloxy group, a phenylsulfonyloxy group, and a p-tolylsulfonyloxy group.

The 2-substituted anilino-4 (3H)-of the present invention
In the pyrimidinone derivative (1), X is preferably a halogen atom, an alkyl group, a haloalkyl group or a nitro group, and R ⁴ is an alkoxy (alkoxycarbonyl) methyl group, from the viewpoint of biological activity as a pesticide. It is a pyrimidinone derivative.

The compound of the present invention has isomers such as optical isomers, diastereomers and geometric isomers depending on the structure. The present invention includes all of them. Each of these isomers can be obtained by isolation from a mixture or by selective production according to a known method. When the compound of the present invention is used as a pesticidal agent, each isomer may be isolated and used, or may be used alone or as a mixture of isomers.

Next, the 2-anilino-4 (3H) of the present invention is used.
-The method for producing the pyrimidinone derivative (1) will be described in detail. The 2-anilino-4 (3H) -pyrimidinone derivative (1) of the present invention can be produced by the method exemplified in the following production method-1.

Production method-1 is based on 2-anilino-4 (3
This is a method for producing a 2-anilino-4 (3H) -pyrimidinone derivative (1) through the introduction of a substituent on the nitrogen atom at position 2 of the (H) -pyrimidinone derivative (3).

[0030]

Embedded image

Wherein R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ ,
X, m, n and L represent the same meaning as described above. )

Step-1 comprises 2-anilino-4 (3H)-
The pyrimidinone derivative (3) is used as a raw material, and is reacted with the reagent (4) in the presence of a base to give the 2-anilino-4 of the present invention.
This is a step of producing a (3H) -pyrimidinone derivative (1).

This reaction is performed in the presence of a base. As the base, sodium hydride, potassium hydride, lithium amide, sodium amide, lithium diisopropylamide (LDA), butyl lithium, tert-butyl lithium, trimethylsilyl lithium, lithium hexamethyldisilazide, sodium carbonate, potassium carbonate, acetic acid Alkali metal bases such as sodium, potassium acetate, sodium methoxide, sodium ethoxide, potassium tert-butoxide, triethylamine, diisopropylethylamine, tributylamine, N-methylmorpholine, N, N-dimethylaniline (DMA), N, N -Diethylaniline, 4-tert-butyl-N, N-dimethylaniline, pyridine, 4- (dimethylamino) pyridine (DMAP), picoline, lutidine, 1,5-diazabicyclic [4. 3.0] -5-nonene (DBN),
1,8-diazabicyclo [5.4.0] -7-undecene (DBU), 1,4-diazabicyclo [2.2.2]
Organic bases such as octane (DABCO) and imidazole can be used. By using 1 to 2 equivalents of the base with respect to the substrate, the desired product can be obtained in good yield.

This reaction can be carried out in a solvent, and any solvent which does not harm the reaction can be used. As the solvent, N, N-dimethylformamide (D
MF), amide solvents such as N, N-dimethylacetamide, N-methylpyrrolidone, nitrile solvents such as acetonitrile and propionitrile, aromatic hydrocarbon solvents such as benzene, toluene, xylene and chlorobenzene, pentane and hexane , Octane and other aliphatic hydrocarbon solvents, diethyl ether, diisopropyl ether, tetrahydrofuran (THF), dimethoxyethane (DM
E) An ether solvent such as 1,4-dioxane, dimethyl sulfoxide (DMSO), or a mixed solvent thereof can be used.

The reaction can be carried out at a temperature appropriately selected from the range of -20.degree. C. to the reflux temperature of the solvent to obtain the desired product in good yield.

In this step-1, 18 as a catalyst is used.
Polyethers such as crown-6, 15-crown-5, 12-crown-4, quaternary ammonium salts such as tetrabutylammonium bromide, tetrabutylammonium sulfate and tetraethylammonium iodide; potassium iodide; By using an alkali metal halide such as potassium iodide or sodium iodide, the desired product can be obtained with higher yield.

Some of the reagents represented by the general formula (4) used in Production Method-1 can be easily obtained, but can be produced, for example, by the method exemplified in Production Method-2.

[0038]

Embedded image

(In the formula, R ⁴ , R ⁵ , R ⁶ , L and n have the same meanings as described above. M represents a hydroxy group or a hydrogen atom.) In the general formula (4a), M is a hydrogen atom. , N is 0, the active hydrogen represented by M can be directly converted into a reagent represented by the general formula (4) wherein L is a halogen atom. This reaction can be carried out by using a halogenating agent. Examples of the halogenating agent include fluorine, chlorine, bromine, iodine, sulfuryl chloride, N-chlorosuccinimide, N-bromosuccinimide, and N-iodosuccinimide. Halogenating agents such as acid imide, tert-butyl hypochlorite, diethylaminosulfur trifluoride, carbon tetrachloride / triphenylphosphine, and carbon tetrabromide / triphenylphosphine can be used. At this time, the base is 1 to 1 with respect to the substrate.
By using 2 equivalents, the desired product can be obtained in good yield.

This reaction can be carried out in a solvent, and any solvent which does not harm the reaction can be used. Examples of the solvent include aromatic hydrocarbon solvents such as chlorobenzene and dichlorobenzene, aliphatic hydrocarbon solvents such as pentane, hexane and octane, and ether solvents such as diethyl ether, diisopropyl ether, THF, DME and 1,4-dioxane. Solvents, halogen-based solvents such as chloroform, dichloromethane and carbon tetrachloride, organic acid-based solvents such as acetic acid and propionic acid, and mixed solvents thereof can be used. The reaction can be carried out at a temperature appropriately selected from the range of −20 ° C. to the reflux temperature of the solvent to obtain the desired product in good yield.

Further, in the general formula (4a), when M is a hydroxy group and n is not 0, triphenylphosphine / bromine, triphenylphosphine / chlorine, carbon tetrachloride / triphenylphosphine, carbon tetrabromide / The reagent represented by the general formula (4) wherein L is a halogen atom can be produced by a deoxygenating halogenation method using a halogenating reagent such as triphenylphosphine.

This reaction can be carried out in a solvent, and any solvent which does not harm the reaction can be used. As the solvent, benzonitrile, acetonitrile,
DMF or the like can be used. Reaction is -20 ° C
By performing the reaction at a temperature appropriately selected from the range of the solvent reflux temperature, the desired product can be obtained in good yield.

When M is a hydroxy group and n is not 0 in the general formula (4a), this is substituted with methylsulfonyl chloride, trifluoromethylsulfonyl chloride, phenylsulfonyl chloride, p-tolylsulfonyl chloride and the like. By reacting the sulfonyl chloride in the presence of a base, a reagent represented by the general formula (4) wherein L is a substituted sulfonyloxy group can be produced.

This reaction can be carried out in a solvent, and any solvent which does not harm the reaction can be used. Examples of the solvent include aromatic hydrocarbon solvents such as toluene, xylene, chlorobenzene, and dichlorobenzene; pentane, hexane, and aliphatic hydrocarbon solvents such as octane;
Diethyl ether, diisopropyl ether, THF,
Ether solvents such as DME and 1,4-dioxane; halogen solvents such as chloroform, dichloromethane and carbon tetrachloride; ketone solvents such as acetone and methyl ethyl ketone (MEK); ester solvents such as ethyl acetate and propyl acetate; acetonitrile And a nitrile solvent such as propionitrile, or a mixed solvent thereof. The reaction can be carried out at a temperature appropriately selected from the range of 0 ° C. to the solvent reflux temperature to obtain the desired product in good yield.

In the production method-1, a part of the 2-anilino-pyrimidinone derivative (3) used as a raw material for producing the 2-anilino-4 (3H) -pyrimidinone derivative (1) of the present invention is described in WO93 / 21162. (CN1079736, EP
636615, US Pat. No. 5,518,194, JP-A-06-32
1913), JP-A-07-89941, WO98 / 51
152 and WO98 / 51675, but can be produced by the method described in the following production method-3.

[0046]

Embedded image

(Wherein, R ⁷ and R ⁸ represent a C ₁ -C ₆ alkyl group, R ^2a represents a hydrogen atom, R ^2b represents a halogen atom, and R ¹ , R ³ , L, X and m Represents the same meaning as described above.)

Step-3 is a step of producing a 2-mercaptopyrimidinone derivative (7) by reacting the isothiocyanate derivative (6) with the 3-aminoacrylic acid ester derivative (5).

The reaction can be carried out in the presence of a base, such as triethylamine, diisopropylethylamine, tributylamine, N-methylmorpholine,
MA, N, N-diethylaniline, 4-tert-butyl-N, N-dimethylaniline, pyridine, DMAP,
Organic bases such as picoline, lutidine, DBU, DABCO, imidazole, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, sodium acetate,
Potassium acetate, sodium methoxide, sodium ethoxide, potassium-tert-butoxide, sodium hydride, potassium hydride, lithium amide, sodium amide, butyllithium, tert-butyllithium,
An alkali metal base such as LDA, trimethylsilyllithium and lithium hexamethyldisilazide can be used. The target compound can be obtained in good yield by reacting the base with 1.0 to 2.0 equivalents of the substrate.

This reaction can be carried out in a solvent, and any solvent which does not harm the reaction can be used. Examples of the solvent include aromatic hydrocarbon solvents such as benzene, toluene, xylene and chlorobenzene, aliphatic hydrocarbon solvents such as pentane, hexane and octane, diethyl ether, diisopropyl ether, THF, DME,
Ether solvents such as 1,4-dioxane, acetone, M
Ketones such as EK and cyclohexanone, chloroform,
Halogen-based solvents such as dichloromethane, acetonitrile,
Nitrile solvents such as propionitrile, ethyl acetate, propyl acetate, butyl acetate, ester solvents such as methyl propionate, DMF, N, N-dimethylacetamide;
Amide solvents such as N-methylpyrrolidone (NMP), alcohol solvents such as methanol (MeOH), ethanol (EtOH), and isopropyl alcohol; DMSO;
Water or a mixed solvent thereof can be used.

The reaction can be carried out at a temperature appropriately selected from the range of -78 ° C to the reflux temperature of the solvent, although it varies depending on the base used and the reaction conditions.

A part of the isothiocyanate derivative (6) used as a raw material in this step is commercially available and can be easily obtained. Further, for example, a method of reacting the corresponding amine with thiophosgene, a method of isomerizing thiocyanate (Japanese Patent Application Laid-Open No. 5-43541), a method of reacting the corresponding amine with carbon disulfide in the presence of a tertiary amine, followed by methyl chloroformate (J. Am. Chem. Soc., 81,
4328 (1959), WO92 / 13835) or a method of reacting corresponding alkenyl halides with potassium thiocyanate or sodium thiocyanate (J. Am. Chem. Soc., 59, 2012 (19)
37)) and the like. 3-aminoacrylic acid ester derivative (5) which is a raw material of this step
Is commercially available and can be easily obtained, but can also be produced by a known method (for example, JP-A-05-140060).

In the step-4, the 2-mercaptopyrimidinone derivative (7) is reacted with an alkylating agent (8) in the presence of a base to alkylate the sulfur atom, thereby obtaining a 2-alkylthiopyrimidinone derivative (9a). ).

The reaction needs to be performed in the presence of a base. As the base, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, sodium acetate, potassium acetate, sodium methoxide, sodium ethoxide, potassium-tert-butoxide, sodium hydride, potassium hydride, sodium amide, butyl Alkali metal bases such as lithium, tert-butyllithium, LDA, trimethylsilyllithium, lithium hexamethyldisilazide, triethylamine, diisopropylethylamine, tributylamine, N-methylmorpholine, DMA, N, N-diethylaniline, 4-t
tert-butyl-N, N-dimethylaniline, pyridine, DMAP, picoline, lutidine, DBU, DABC
Organic bases such as O and imidazole can be used. Although the stoichiometric amount of the base is sufficient with respect to the substrate, there is no problem even if it is used in excess, and the desired product can be obtained in good yield.

This reaction is preferably carried out in a solvent. As the solvent, any solvent that does not harm the reaction can be used, and benzene, toluene, xylene,
Aromatic hydrocarbon solvents such as chlorobenzene, pentane,
Aliphatic hydrocarbon solvents such as hexane and octane, diethyl ether, diisopropyl ether, THF, DM
E, ether solvents such as 1,4-dioxane, ketones such as acetone, MEK, cyclohexanone, halogen solvents such as chloroform and dichloromethane, nitrile solvents such as acetonitrile and propionitrile, ethyl acetate, propyl acetate and acetic acid Butyl, ester solvents such as methyl propionate, amide solvents such as DMF, N, N-dimethylacetamide, NMP, MeOH, EtOH,
Alcohol solvents such as isopropyl alcohol, DMS
O, water, or a mixed solvent thereof can be used.

The reaction can be carried out at a temperature appropriately selected from the range of 0 ° C. to the reflux temperature of the solvent, although it varies depending on the base used and the reaction conditions.

In the alkylating agent (8), the leaving group represented by L includes a halogen atom such as a chlorine atom, a bromine atom and an iodine atom, a methylsulfonyloxy group, a phenylsulfonyloxy group and a p-tolylsulfonyloxy group. And other substituted sulfonyloxy groups.

Step-5 is a step of oxidizing the 2-alkylthiopyrimidinone derivative (9a) to produce a 2-alkylsulfonylpyrimidinone derivative (9b).

This step can be performed using an oxidizing agent.
As the oxidizing agent to be used, oxidizing agents commonly used for oxidizing sulfur atoms, for example, peracids such as peracetic acid, perbenzoic acid, m-chloroperbenzoic acid, or hydrogen peroxide, nitric acid, potassium permanganate, etc. Oxidizing agents can be used. By reacting the oxidizing agent with the substrate in an amount of 2.0 to 4.0 equivalents, the desired product can be obtained in high yield.

This reaction is preferably carried out in a solvent, for example, aromatic hydrocarbon solvents such as benzene, toluene, xylene and chlorobenzene, aliphatic hydrocarbon solvents such as pentane, hexane and octane, diethyl ether and diisopropyl ether. Does not harm the reaction of ether solvents such as THF, DME, 1,4-dioxane, ketones such as acetone, MEK, cyclohexanone, halogen solvents such as chloroform and dichloromethane, water, or a mixed solvent thereof. Any solvent can be used.

The reaction can be carried out at a temperature appropriately selected from the range of 0 ° C. to the reflux temperature of the solvent, although it varies depending on the oxidizing agent used and the reaction conditions.

In Steps 6 and 7, the 2-alkylthiopyrimidinone derivative (9a) or 2-alkylsulfonylpyrimidinone derivative (9b) is used as a starting material, and is reacted with an aniline (10). This is a step of producing the anilinopyrimidinone derivative (3a).

It is preferable to carry out both of the reactions of Step-6 and Step-7 in the presence of a base in terms of good yield. As the base, sodium hydride, potassium hydride, lithium amide, sodium amide, LDA, butyllithium, tert-butyllithium, trimethylsilyllithium, lithium hexamethyldisilazide, sodium carbonate, potassium carbonate, sodium acetate, potassium acetate, Alkali metal bases such as sodium methoxide, sodium ethoxide, potassium-tert-butoxide, triethylamine, diisopropylethylamine, tributylamine, N-methylmorpholine, DMA, N, N-diethylaniline, 4-tert-butyl-N, N -Organic bases such as dimethylaniline, pyridine, DMAP, picoline, lutidine, DBU, DABCO, imidazole and the like can be used. By using 1.0 to 2.0 equivalents of the base relative to the substrate, the desired product can be obtained in good yield.

These reactions can be carried out in a solvent, and any solvent which does not harm the reaction can be used. Examples of the solvent include amide solvents such as DMF, N, N-dimethylacetamide, NMP, acetonitrile,
Nitrile solvents such as propionitrile, aromatic hydrocarbon solvents such as benzene, toluene, xylene and chlorobenzene, aliphatic hydrocarbon solvents such as pentane, hexane and octane, diethyl ether, diisopropyl ether, THF, DME, 1 Any solvent which does not hinder the reaction, such as an ether solvent such as 1,4-dioxane, DMSO, or a mixed solvent thereof can be used.

The reaction can be carried out at a temperature appropriately selected from the range of -78 ° C to the reflux temperature of the solvent to obtain the desired product in good yield.

Step-8 includes 2-anilino-4 (3H)-
This is a step of halogenating the 5-position of the pyrimidine ring using the pyrimidinone derivative (3a) as a raw material to produce a 2-anilino-4 (3H) -pyrimidinone derivative (3b). Halogenation can be carried out by using a halogenating agent. Examples of the halogenating agent used include fluorine, chlorine, bromine, iodine, sulfuryl chloride, N-chlorosuccinimide, N-bromosuccinimide, and N-bromosuccinimide. Halogenating agents such as iodosuccinimide, tert-butyl hypochlorite, diethylaminosulfur trifluoride, carbon tetrachloride / triphenylphosphine, and carbon tetrabromide / triphenylphosphine can be used. On this occasion,
By using 1 to 2 equivalents of the base with respect to the substrate, the desired product can be obtained in good yield.

This reaction can be carried out in a solvent, and any solvent which does not harm the reaction can be used. Examples of the solvent include aromatic hydrocarbon solvents such as chlorobenzene and dichlorobenzene, aliphatic hydrocarbon solvents such as pentane, hexane and octane, and ether solvents such as diethyl ether, diisopropyl ether, THF, DME and 1,4-dioxane. Solvents, halogen-based solvents such as chloroform, dichloromethane and carbon tetrachloride, organic acid-based solvents such as acetic acid and propionic acid, and mixed solvents thereof can be used.

The reaction can be carried out at a temperature appropriately selected from the range of -20 ° C. to the reflux temperature of the solvent to obtain the desired product in good yield.

The pesticidal composition containing the compound of the present invention as an active ingredient can be used for repelling pests in a wide range of fields such as agriculture, forestry, animal husbandry, fisheries, and product preservation and public health in these industries. Effective for extermination and control.

The compound of the present invention is particularly useful for agriculture, forestry, and the like, specifically for growing crops, and for repelling pests that cause damage to crops, trees, ornamental plants, etc., and pests in public health situations. Excellent effect as insecticide and acaricide used for extermination and control.

The specific use scene, target pest,
The method of use and the like will be described, but the present invention is not limited to the following description. More specifically, the exemplified pests do not limit the target pests, and the exemplified pests also include adults, larvae, eggs and the like.

(A) Agriculture, forestry scene, etc.

The compounds of the present invention can be used in agricultural crops such as food crops (rice, wheat, corn, potato, sweet potato, beans, etc.),
Vegetables (brassic crops, spinach, eggplant, tomato, leek, etc.), fruit trees (citrus, apple, grape, thigh, etc.), special crops (tobacco, tea, sugar beet, sugar cane, cotton, olives, etc.), pasture -Arthropods, molluscs, etc. that may damage feed crops (sorghum, grasses, legumes, etc.) and ornamental plants (herbs, flowers, garden trees, etc.) It is effective for repelling and controlling pests such as nematodes and various fungi.

Furthermore, the compounds of the present invention are harmful when storing harvested products from the above-mentioned crops, such as cereals, fruits, nuts, spices and tobacco, and products which have been subjected to drying, powdering and the like. It is also effective for repelling and extermination of living things. It is also effective in protecting standing trees, fallen trees, processed wood, stored wood, and the like from damage by pests such as termites and beetles.

Specific pests include, for example, those belonging to the phylum Arthropoda, Mollusca and Nematoda:
The following can be mentioned.

Examples of the arthropod phylum Insecta include the following.

As Lepidoptera, for example, Spodoptera litura,
Noctuidae such as Bombyx mori, armyworm, Tamanaginiwawa, etc .; Saga family such as P. japonicus; Coleoptera family such as chanococcus terrestris, Nashihimesingui, etc .; Scrophulariaceae; Scarabaeaceae, such as Scarabaeidae; Scarabaeidae, such as Kachinohetoshiga; Scarabaeaceae, such as cottontail beetle; Family Papilionidae such as Swallowtails; White butterfly butterflies such as Monstroenidae; Lycaenidae such as Uranamisujimi; Paeoniaceae such as Artemisia edulis; Sphingidae such as prawn glass sparrows; Lymantriidae such as Arna Pseudoconspersa; moth Department;
Higrigidae, such as American White-Throated, can be mentioned.

As the Coleoptera, for example, Scarabaeidae such as Scutellaria serrata, Koohamamuguri, and Mamekogane; Eclectidae such as Coleoptera; Tenebrionidae such as Coleoptera cricket; Coccinellidae such as Coleoptera; Beetles, beetles, beetles, leaf beetles, rice beetles, etc .; beetles, such as the weevil weevil; beetles, such as the weevil weevil; weevils, such as the weevil, weevil, etc. it can.

As the Hemiptera, for example, stink bugs such as chafered stink bugs and sting bugs; crested stink bugs such as pear stink bugs; crested stink bugs such as crested stink bugs; Stork beetles, such as red beetles; etc .; Gung beetles, such as Nashigumbai; Scarabaeidae, such as Usmidreme turtles; Cicadas, such as Nichinisemi; Coleoptera, such as grapes Awabuki; Lepidoptera, such as the leafhopper; leafhoppers, such as the black leafhopper; planthoppers, such as the brown planthopper and the brown planthopper;
Dermatophylidae, such as Aobahagoromo; Phyllididae, such as pear lice; Whiteflies, such as whitefly and silverleaf whitefly; Phylloceraceae, such as crimson aphid; Aphididae; Pseudococcidae, such as Iseria coccidae; Pseudococcidae, such as Citrus scutella; Psychococcidae, such as ruby beetle;

Further, the thrips include Thrips (Thysanoptera: Thrips), Thrips palmi, Thrips palmi, Thrips palmi, etc .;
And Thrips palmiaceae, such as rice thrips.

The Hymenoptera include, for example, honeybees such as wasps, honeybees such as apple honeybees, honeybees such as chestnut wasps, and honeybees such as barnacle honeybees. As the diptera, for example, soybean flies, such as soybean flies; flies, such as sea flies; flies, such as rice fly; flies, such as Drosophila;
Examples of the family Lepidoptera, such as Papilionidae; The Orthoptera includes, for example, grasshoppers such as crickets; crickets such as green worms; As the order of the Collembola,
For example, Maltwig beetles, such as the yellow beetle; and White beetle, such as Matsumoto beetle. Examples of the termites include termites such as Taiwan termites, and examples of the earwigs include earwigs such as earwigs.

Examples of the arthropod phylum shell network and spider web include the following.

As the isopods of the crustacean, there can be mentioned, for example, the family Araceae, such as the Okadan Bug.

Examples of the acarid mites of the order of the Arachnida include, for example, Dermatophagoids such as Dermatophagoids and Cyclamenidae; Dermatophagoids such as Pteridoderidae;
Examples of spider mites such as apple spider mites; rust mites such as citrus red mite, apple rust mite, and red mite;

The mollusc phylum Gastropods include, for example, the midgastropods of the gastropods, such as the scallop apple, and the stalk eyes such as African snails, slugs, skull slugs, chakoura slugs, and scabies. be able to.

The followings can be exemplified as the linear phylum network and the tail line network.

Examples of the genus Oribatida include, for example, Anguinae family such as Imogusa nematode; Tyrencholinex family such as Namiikusu nematode; Platylenx family such as Kitanegusa nematode and Minamigusa nematode; Heterodera family such as potato cyst nematode; meloidoid family such as sweet potato nematode; cliconema family such as locust nematode; nototilenic family such as strawberry nematode; and aphelencoide family such as strawberry nematode. Examples of the order Oxodidae include the Longiduridae family, such as the genus Oxodidae, and the Trichodulaceae family, such as the Yumihari nematode.

Further, the compound of the present invention is also effective for repelling, controlling and controlling pests that damage trees or affect tree vigor such as natural forests, artificial forests and urban green spaces. In such a situation, specific pests include the following.

Examples of the arthropod phylum Insecta and spider webs include the following.

Examples of the Lepidoptera include the stag beetles such as sugidokuga and the gypsy moth; the scorpionaceae such as matsukareha and tsukakareha; the scrofaaceae such as larch madara moga; the noctaceae such as kaburayaga; and the oysteraceae such as larchite hikihamaki, kurimiga and sugikasaga. Hirrigidae, such as A. americana; Moglitiviga, such as Shiimoglitiviga;

As the Coleoptera, for example, Scarabaeidae, such as Hemerocarpus and Nagachacogane; Beetles, such as Pleurotus terrestris; Cerambycidae, such as pine beetles; Chrysomelidae, such as cedar beetles; Weevils; Weevils, such as Weevil; Weevils, such as pine bark beetle and bark beetle;

Further, as the Hemiptera, for example, aphid family such as Abies sachalinensis aphid; Casa aphid family such as Ezomatsuka aphid; Marsupidae family such as Cryptomeria aphid; .

The Hymenoptera include, for example, honeybees such as Larch red wasp; pine wasps such as pine tree wasps; and honeybees such as chestnut wasps.
Examples of the diptera include a gallaceae family such as a giant moth, etc .; a genus family such as a pine fly, and a flies which include adults, larvae, and eggs.

Examples of the spiders of the order Arachnida include spider mites and spider mites.

Examples of the nematodes of the order Nematoda, Nematoda, include Parasitaferrenidae, such as pine wood nematodes.

The pesticidal composition containing the compound of the present invention as an active ingredient can be used alone or in addition to other active compounds, such as insecticides, in the above-mentioned preparations effective in agriculture and forestry, and in any use form prepared by the preparations. It can be used in combination or as an admixture with an agent, acaricide, nematicide, fungicide, synergist, plant regulator, herbicide, poison bait and the like.

The form of use is arbitrary, for example, wettable powders, wettable powders, aqueous solvents, emulsions, solutions, suspensions in water, emulsions in water, etc., capsules, powders, granules, aerosols. Agents and the like. The content of the active ingredient compound such as the compound of the present invention in these preparations is optional, but is usually 0.001 to 95% by weight, preferably 0.1 to 60% by weight in total of the active ingredients.

The method of use depends on the type and amount of pests,
Depending on the type of crops, trees, etc. and the cultivation form / growing state of the target, for example, arthropods, gastropods, nematodes, etc. are usually affected by these pests, Or where there is a possibility that damage will occur, in general, the effective ingredient amount is 0.1 per 10 ares.
１０００1000 g, preferably 1-100 g may be applied.

Specific application methods include, for example, the above-mentioned wettable powders, wettable powders for granules, aqueous solvents, emulsions, solutions, suspensions in water and emulsions in water, and capsules and the like. Diluted with water, 10-100 per 10 ares depending on the type of crop, tree, etc. and cultivation form / growing state
What is necessary is just to spray to crops, trees, etc. in the range of 0 liter. In the case of powders and aerosols, the preparations may be applied to crops, trees, etc. within the range of the above-mentioned usage.

When the target pest infects crops, trees, etc. mainly in soil, for example, wettable powder, wettable powder, aqueous solvent, emulsion, liquid, suspension in water, emulsion in water It is sufficient to dilute a flowable agent such as an agent, a capsule agent or the like with water, and to apply generally in the range of 5 to 500 liters per 10 ares. At this time, the medicine may be sprayed on the soil surface so as to be even over the entire application area, or may be irrigated into the soil. When the form of the preparation is a powder or granule, the preparation may be sprayed on the soil surface as it is so as to be uniform over the entire area to be applied. Also, when spraying or irrigation, it may be applied only around the seeds, crops, trees, etc. that you want to protect from damage by pests, or may be plowed during or after spraying to disperse the active ingredient mechanically. Good.

Further, a pesticidal composition containing the compound of the present invention as an active ingredient may be adhered around plant seeds by a known method. By such a treatment, not only can the pests in the soil be prevented from being damaged after sowing of the seeds, but also the foliage and flowers of the plant,
Fruits and the like can also be protected from damage by pests.

When protecting the above-mentioned trees, fallen trees, processed wood, stored wood, etc. from damage by termites, beetles, etc., for example, an oil agent is applied to the surrounding soil of trees, wood, etc.
Examples of the method include spraying, injecting, irrigation, and coating an emulsion, a wettable powder, and a sol, and spraying a drug in a use form such as a powder or a granule. In such a situation, the pesticidal composition containing the compound of the present invention as an active ingredient alone or other active compounds such as insecticides, acaricides, nematicides, fungicides, repellents, synergists, etc. Can be used in combination or as a mixture.

The content of the active ingredient compound such as the compound of the present invention in these preparations is arbitrary, but is usually from 0.0001 to 95% by weight of the total amount of the active ingredient, such as oils, powders, granules and the like. Is preferably 0.005 to 10% by weight, and in emulsions, wettable powders and sols, it is preferably 0.01 to 50% by weight. Specifically, for example, when controlling or controlling termites, beetles, etc., 0.01 to 100 g of the active ingredient compound per 1 m ² may be sprayed on the soil or wood surface.

(B) Livestock industry, fishing industry scene, etc.

The pesticidal composition containing the compound of the present invention as an active ingredient is infested internally or externally with animals such as pets bred in the livestock industry, the fishery industry, and at home, and eats and sucks blood from the skin and the like. It is effective for repelling, exterminating, and controlling pests such as arthropods, nematodes, flukes, tapeworms, and protozoa that cause direct harm, such as the spread of diseases, etc. Yes,
It can also be used for the prevention and treatment of diseases related to these pests.

The target animals include vertebrates, for example, livestock vertebrates such as cattle, sheep, goats, horses, pigs, and other livestock and farmed fish; and poultry, dogs, cats, mice, rats, and the like.
Rodents such as hamsters and squirrels; carnivores such as ferrets; pets and experimental animals such as fish;

Among the pests, examples of the arthropod phylum Insecta and spider webs include the following.

Examples of the dipterans include the family Afidae such as Yamatobu, Tsumetogebuyu and Red-tailed fly; Houseflies such as blowfly, housefly and sandflies; Horseflies such as horseflies; Cowflies such as cowflies; Dermatophagidae such as Pteromorphidae; Laceae family such as Aedes aerariae; And the like.

[0109] Examples of the Coleoptera include cat flea,
Human flea family such as dog flea can be mentioned. Examples of the lice include Liceflies, such as pig lice and bovine lice; Liceflies, such as horse lice; Liceflies, such as bovine lice; and Liceflies, such as chicken lice.

Examples of the acarids of the class Arachnida: Arachnidae, Ixodid ticks, Oxodid ticks, and Ixodid ticks; Oxodidae, such as Trichodermic mites; Occidental, such as mites; Dermatophagoids such as Dermatophagoids and Dermatophagoides mite; Dermatophagoids such as Dermatophagoides farinae and Bovine Dermatophagoids.

Examples of the nematodes of the nematode phylum include the following.

[0112] As the nematodes, for example, caterpillars, pig nematodes,
Pig lungworm, ciliate nematode, bovine intestinal nodule and the like can be mentioned. As the roundworm, for example, roundworm, roundworm of chicken, etc. can be mentioned.

[0113] Examples of the genus Pteratozoa include Schistosoma japonicum, Hepatica, Liver fluke, Westermani lung fluke, Japanese chicken egg fluke, and the like.

Examples of tapeworms include foliate tapeworms, tapeworms, Beneden tapeworms, square tapeworms, striated tapeworms, and tapeworms.

In the class Protozoa, the flagellates are, for example, Histomonas, etc., as the protoflagellate, for example, Leishmania, Trypanosoma, etc., and for the polyflagellate, for example, Giardia, etc., and Trichomonas. Examples of the eye include Trichomonas and the like. Further, as the amoeba of the fleshy class, for example, Entamoeba and the like, and as the pyroplasma of the sporozoa, for example, Theilaria
, Babesia, etc., as late-sporospore subclasses, for example, Eim
eria, Plasmodium, Toxoplasma and the like.

The pesticidal composition containing the compound of the present invention as an active ingredient can be used in the above-mentioned preparations effective in the livestock industry and the fishing industry, and in any use form prepared by the preparations.
It can be used alone or in combination with other active compounds, such as insecticides, acaricides, nematicides, fungicides, synergists, plant regulators, herbicides and baits, or as admixtures.

[0117] Specific application methods include, for example, a compounded pharmaceutical composition which can be mixed into feeds of livestock and pets, or which can be orally ingested, such as tablets and pills containing a pharmaceutically acceptable carrier or coating substance. Orally or as a capsule, paste, gel, beverage, medicated feed, medicinal drinking water, medicated bait, sustained release large pills, other sustained release device retained in the gastrointestinal tract, or spray , Powder, grease, cream, ointment, emulsion, lotion, spot-on, pour-on, shampoo and the like.

As a method of transdermal administration or topical administration, a device (for example, a collar, a medallion, an ear tag, etc.) attached to an animal so as to control arthropods locally or systemically can also be used.

Specific oral and transdermal administration methods when used as an anthelmintic for livestock and pets are shown below. In the present invention, these administration methods are not necessarily limited to the following description. is not.

When administered orally as a pharmaceutical drink preparation, it is usually dissolved in a suitable non-toxic solvent or water together with a suspending agent such as bentonite or a wetting agent or other excipients, to give a suspension. Alternatively, a dispersion may be used, and an antifoaming agent may be contained as necessary. Beverage preparations generally contain the active compound in an amount of 0.01 to 1.0% by weight, preferably 0.01 to 0.1% by weight.

For oral administration in a dry solid unit dosage form, capsules, pills or tablets containing a predetermined amount of the active ingredient compound are usually employed. These forms of use include diluents, fillers, disintegrants and / or binders such as starch, lactose, talc, or the like, in which the active ingredient is suitably comminuted.
It is produced by mixing homogeneously with magnesium stearate, vegetable rubber and the like. In such a unit-use prescription, the weight and content of the anthelmintic may be appropriately set according to the type of host animal to be treated, the degree of infection, the type of parasite, and the weight of the host.

When administered via feed, there may be mentioned, for example, a method in which the active ingredient compound is uniformly dispersed in the feed, a method in which the drug is used as a top dressing, or a method in the form of pellets. In order to achieve an antiparasitic effect, the active ingredient compound is usually present in the final feed at 0.0001 to 0.05% by weight, preferably at 0.000%.
0.05 to 0.01% by weight.

When dissolved or dispersed in a liquid carrier excipient, the compound may be parenterally administered to the animal by intragastric, intramuscular, intratracheal or subcutaneous injection. Because of parenteral administration, the active ingredient compounds are preferably mixed with vegetable oils, such as peanut oil, cottonseed oil, and the like. In such a formulation,
Generally, it contains 0.05 to 50% by weight, preferably 0.1 to 0.2% by weight of the active ingredient compound. Also, DMSO
Alternatively, a formulation mixed with a carrier such as a hydrocarbon solvent can be directly and topically applied to the external surface of livestock or pets by spraying or direct pouring.

(C) Public health scene, etc.

The pesticidal composition containing the compound of the present invention as an active ingredient has adverse effects on clothes, food, and living environment, further harms the human body, and carries and mediates pathogens. It is also effective in repelling, controlling and controlling pests for maintaining public health, etc.

Specifically, the pesticidal composition containing the compound of the present invention as an active ingredient includes, for example, wood products such as dwelling itself and indoor / outdoor wood, wooden furniture, stored food, clothing, books,
Lepidoptera, beetles, spots, cockroaches, flies that damage animal products (skins, wool, wool, feathers, etc.) and plant products (clothing, paper, etc.) and have a negative impact on sanitary life It is effective for repelling, extermination and control of mites. Specific examples of such pests in public health situations include the following.

Examples of the arthropod phylum Insecta include the following.

As the Lepidoptera, for example, the family Podidae such as Moncaria aegypti; the plagiocephalids such as Kunugikareha; the Iragidae such as Aoiraga; the Malagalidae such as Takenohosokuroba; Gibionidae such as Bakuga; and Hirugokogae such as Iga and Kiga. As the Coleoptera, for example, the family Ceratopogonidae such as Blue horned beetle; The beetle family such as Mamehanmyo; The bee family Coleoptera such as Aoba arigata Hanekushi; The weevil weeds such as the weevil, the weevil and the weevil Beetles; beetles; Lepidoptera, such as Lepidoptera, etc .; Psychodomice family, such as Coleoptera crispinae and Coni longicum beetle; Kill.

The Hymenoptera include, for example, wasp family such as wasp, ant family such as giant ant, and bee family such as beetle. As the diptera, for example, mosquitoes such as yamato falcon;
Brassicaceae such as brassicae;
Ascidian family such as Asimadarabu;
Houseflies such as house flies; flies such as house flies; and fly families such as blackflies; flies and flies; and fly flies such as Drosophila; and cheese flies such as cheese flies. Examples of the order Lepidoptera include a flea family such as a human flea. As the order of the viscera, there may be mentioned, for example, the family Pteridomycetes, such as purple pit viper. Examples of the cockroaches include the German cockroaches such as German cockroaches and Chinese cockroaches; and the cockroaches such as American cockroaches, black cockroaches, and black cockroaches. The Orthoptera includes, for example, the family Corrugidae, such as Madara camphoridae and Anopheles camphorata. As the louse, for example, lice of the head lice such as head lice; lice of the lice such as lice may be mentioned. Examples of the Hemiptera include bed bugs such as bed bugs; and bugs such as bed bugs.

Examples of the termites include the termites of the termites such as the termites and termites; the termites of the termites such as the termites; the termites of the termites such as termites; And the like. As the spots, for example, spots such as yamatos spots and sea skewers can be mentioned.

Examples of arthropod spiders include the following.

As the mites, for example, ticks such as Schurze ticks; Dermatophagoides, such as house dust mites; Cyperidae, such as Thrips ticks; Lice mites, such as lice mites;
Acariidae such as Dermatophagoides, Dermatophagoides such as Dermatophagoides pteronyssinus; Dermatophagoids such as Dermatophagoides pteronyssinus; Dermatidae such as Dermatophagoides mite; Dermatidae such as Dermatophagoids and Dermatophagoides; Dermatidae such as Dermatophagoides.

Examples of the true spiders include, but are not limited to, the spider spiders such as birch spiders; the spiders such as red spiders; Can be mentioned.

As the scorpiones, there may be mentioned, for example, Moleoptera scorpions such as Madara scorpion.

As other arthropod phylums, examples of the order Lepidoptera of the Labiopoda include those of the family Ceratopogonidae, such as Tobism and Aozuchamidae, and those of the order Causticidae include, for example, the family Ceratopogonidae. Examples of the arthropod phylum, Ophiaceae include, for example, Papilionidae such as Toyakesade, and examples of the arthropod, Crustacea, include the Phytopodaceae, such as P.

Further, as the annelid fauna, Lepidoptera,
For example, yamabir family such as yamabir can be mentioned.

The pesticidal composition containing the compound of the present invention as an active ingredient may be used alone or in combination with other active compounds such as insecticides in the above-mentioned preparations effective in public health and in any use forms prepared by the preparations. Miticides, nematicides,
It can be used in combination or as a mixture with fungicides, synergists, plant regulators, herbicides, poison baits and the like.

The form of use is arbitrary. For example, when protecting the above-mentioned animal products and plant products, it is possible to spray oils, emulsions, wettable powders, powders, etc., install resin vaporizers, etc. It can be controlled by methods such as treatment with aerosols, installation of granules, tablets and poison baits, spraying aerosols and the like. The amount of the active ingredient compound in these preparations is 0.0001 to 9
It is preferred to contain 5% by weight.

As an application method, for pests, for example, arthropods that cause direct harm or arthropods that are disease carriers, for example, oils, emulsions, Spraying / injection / irrigation / application of wettable powders, spraying of powders, etc.
A method of treating with a preparation such as an ULV agent can be given. In another formulation form, such as granules, tablets or poison baits, or floating powder,
The granules and the like may be applied by a method such as dropping into a water channel, a well, a reservoir, a water tank, and other flowing or stationary water.

In addition, it is possible to control pests and the like which are also pests in agriculture and forestry in the same manner as described above, and to control flies and the like by mixing them in livestock feed. A method to ensure that the active ingredient is mixed into the feces,
It is also effective to volatilize mosquitoes and the like into the air with an electric mosquito trap.

The preparations in these forms of use may also be present as mixtures with other active compounds, for example insecticides, acaricides, nematicides, fungicides, repellents or synergists. Preferably, these preparations contain the active ingredient compound in a total amount of 0.0001 to 95% by weight.

When protecting a house or wooden furniture from damage by termites or beetles, for example, spraying / injecting / irrigating / applying oils, emulsions, wettable powders and sols to and around them. , Powders, granules, and the like, and spraying the drug in a use form. In such a situation, the compound of the present invention alone or other active compounds,
For example, it can be used in combination or as a mixture with insecticides, acaricides, nematicides, fungicides, repellents, synergists and the like.

The content of the active ingredient compound such as the compound of the present invention in these preparations is arbitrary, but is usually from 0.0001 to 95% by weight in total of the active ingredient, and oils, powders, granules, etc. Is preferably 0.005 to 10% by weight, and in emulsions, wettable powders and sols, it is preferably 0.01 to 50% by weight. Specifically, for example, in the case of controlling and controlling termites and beetles, 0.01 to 100 g of the active ingredient compound per m < ² > may be sprayed around or directly on the surface.

When repelling, exterminating, or controlling pests such as causing harm to the human body or carrying or transmitting pathogens,
In addition to the above, suitable ingestible pharmaceutical compositions such as tablets, pills, capsules, pastes, gels, drinks, medicinal feeds, medicinal products containing pharmaceutically acceptable carriers and coating materials, Oral administration, such as drinking water, medicated bait, sustained release large pills, and other sustained release devices kept in the gastrointestinal tract, or spray, powder,
It can be transdermally administered as grease, cream, ointment, emulsion, lotion, spot-on, pour-on, shampoo, and the like.

Specific pharmaceutical formulations are described in “(B) Livestock Industry,
The formulation can be carried out in the same manner as in the method described in the section "Scenery in the fishing industry".

The compounds of the present invention can be used in combination with other active compounds or as a mixture. The following can be exemplified as more specific active compounds,
It is not limited to these.

As active compounds such as insecticides and acaricides, organic phosphorus agents include, for example, dichlorvos, fenitrothion, malathion, naled, chlorpyrifos, diazinon, tetrachlorovinphos, fenthion, isoxathion, methidathion, salicion, acephate, dimeton- Examples thereof include S-methyl, disulfotone, monocrotophos, azinephosmesyl, parathion, hosalon, pirimiphosmethyl, and prothiophos. Examples of carbamates include metrecarb, fenobucarb, propoxur, carbaryl, ethiophenecarb,
Pirimicarb, bendiocarb, carbosurfan,
Carbofuran, mesomil, thiodicarb and the like can be mentioned.

Examples of the organic chlorine agent include lindane, D
DT, endosulfan, aldrin, chlordane and the like can be mentioned. Examples of the pyrethroids include permethrin, cypermethrin, deltamethrin, cyhalothrin, cyfluthrin, acrinatrine, fenvalerate, etofenprox, silafluofen, fluvalinate, flucitrinate, bifenthrin, arelesrin, phenothrin, fenpropatrine, cyphenothrin, and framethrin, Examples include resmethrin, transfluthrin, praletrin, flufenprox, halofanprox, imiprothrin and the like. Neonicotinoid agents include, for example, imidacloprid, nitenpyram, acetamiprid, tefuranitodine, thiamethoxam, thiacloprid and the like.

Examples of insect growth regulators such as phenylbenzoylurea agents include diflubenzuron, chlorofluazuron, triflumuron, flufenoxuron, hexaflumuron, lufenuron, teflubenzuron, buprofezin, tebufenozide, chromafenozide, methoxyfenozide, cyromazine and the like. be able to.

Examples of the juvenile hormone agent include pyriproxyfen, phenoxycarb, mesoprene, hydroprene and the like.

The insecticidal substances produced by microorganisms include, for example, abamectin, milbemectin, nikkomycin, emamectin benzoate, ivermectin,
Spinosadodo and the like can be mentioned.

As other insecticides, for example, cartap, bensultap, chlorfenapyr, diafenthiuron, nicotine sulfate, methaldehyde, fipronil, pymetrozine, indoxacarb, tolfenpyrad and the like can be mentioned.

As active compounds for miticides, for example, dicophor, phenisobromolate, benzomate, tetradiphone, polynactin complex, amitraz, propargyl, fenbutatin oxide, tricyclohexyltin hydroxide, tebufenpyrad, pyridaben, fenpyroximate, pyrimidifene, fenazaquin, Clofenthedine, hexthiazox, acequinosyl, quinomethionate, phenothiocarb, ethoxazole, bifenazate and the like can be mentioned.

Examples of the active compounds of the nematicide include methyl isocyanate, phosthiazate, oxamyl, mesulfenphos and the like.

As the poison bait, for example, monofluoroacetic acid,
Warfarin, beartetralyl, difacine and the like can be mentioned.

Examples of the fungicidally active compounds include, for example, inorganic copper, organic copper, sulfur, maneb, thiuram, thiadiazine, captan, chlorothalonil, iprovenphos, thiophanatemethyl, benomyl, thiabendazole, iprodione, procymidone, pencyclon, metalaxyl, sandphan, and biletone. , Triflumizole, fenarimol, triforine, dithianone, triazine, fluazinam, probenazole, dietofencarb, isoprothiolane, pyroquilon, iminoctadine acetate,
Eclomesol, dazomet, kresoxime methyl and the like can be mentioned.

Examples of active compounds such as herbicides include bialaphos, sethoxydim, trifluralin, mefenacet and the like.

Examples of the active compounds of the plant regulator include indolebutyric acid, ethephon, 4-CPA and the like.

Examples of the active compounds of the repellent include, for example, carane-3,4-diol, N, N-diethyl-m-triamide (Deet), limonene, linalool, citronellal, menthone, hinokitiol, menthol, graniol, eucalyptol And the like.

Examples of the active compound of the synergist include bis- (2,3,3,3-tetrachloropropyl) ether and N- (2-ethylhexyl) bisclo [2.1.
1] hept-5-ene-2,3-dicarboximide,
α- [2- (2-butoxyethoxy) ethoxy] -4,
5-methylenedioxy-2-propyltoluene and the like can be mentioned.

[0161]

EXAMPLES Hereinafter, the present invention will be described more specifically with reference to Examples, Reference Examples and Test Examples, but the present invention is not limited to the following Examples and Test Examples.

Example 1

[0163]

Embedded image

2- {2-chloro-3,5-bis (trifluoromethyl) phenylamino} -3-propyl-6-trifluoromethyl-4 (3H) -pyrimidinone (1.00 g, 2.1
3 mmol) in acetonitrile (30 mL)
(0.88 g, 6.39 mmol) and 18-crown-6-ether
(0.1 g) was added and the mixture was stirred at room temperature, to which was added crude methyl 1-bromo-1-methoxyacetate (0.78 g, 4.26 mmol), and the mixture was stirred with heating at 60 ° C. for 3 hours. After the completion of the reaction, the solid was separated by filtration, and the filtrate was concentrated under reduced pressure to obtain a crude product. This is 1N
The mixture was poured into a hydrochloric acid aqueous solution, extracted with ethyl acetate, and the extract was washed with water and saturated saline, and the solvent was distilled off. The residue is a silica gel column (Kieselgel60 manufactured by MERCK, 20% AcOEt-Hex)
And purified by N- {2-chloro-3,5-bis (trifluoromethyl) phenyl} -N- (6-oxo-1-propyl-4-trifluoromethyl-1,6-dihydropyrimidine-2- A yellow viscous liquid (0.51 g) of methyl yl) amino (methoxy) acetate was obtained. Yield: 42%; ¹ H-NMR (CDCl
₃ , TMS, ppm): δ0.69 (t, J = 7.6Hz, 3H), 1.0 and 1.4
(m, 2H), 3.5 (m, 2H), 3.65 (s, 3H), 3.77 (s, 3H), 5.45
(s, 1H), 6.62 (s, 1H), 7.71 (s, 1H), 7.97 (s, 1H).

Embodiment 2

[0166]

Embedded image

2- {2-bromo-3,5-bis (trifluoromethyl) phenylamino} -5-chloro-6-trifluoromethyl-3-vinyl-4 (3H) -pyrimidinone
(1.00 g, 1.89 mmol) in acetonitrile (20 mL) was added potassium carbonate (0.78 g, 5.66 mmol) and 18-crown-6.
-Ether (0.1 g) was added and stirred at room temperature, and crude 1-bromo-1-methoxyacetate (0.74 g, 3.77 mmol
l) was added, and the mixture was heated and stirred at 60 ° C. for 3 hours. After the completion of the reaction, the solid was separated by filtration, and the filtrate was concentrated under reduced pressure to obtain a crude product.
This was poured into a 1N aqueous hydrochloric acid solution, extracted with ethyl acetate, and the extract was washed with water and saturated saline, and then the solvent was distilled off. The residue is silica gel column (MERCK Kieselgel60,
20% AcOEt-Hex) and purified by N- ｛2-bromo-3,
5-bis (trifluoromethyl) phenyl} -N- (5-
Chloro-6-oxo-4-trifluoromethyl-1-vinyl-1,6-dihydropyrimidin-2-yl) amino
A yellow viscous liquid of (methoxy) ethyl acetate (1.00 g) was obtained. Yield: 82%; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ1.23 (b
rt, J = 6.8Hz, 3H), 3.57 (br s, 3H), 4.18 (m, 2H), 5.
15 (d, J = 7.2Hz, 1H), 5.47 (d, J = 16Hz, 1H), 5.88 (s, 1
H), 5.89 (dd, J = 7.2 and 16Hz, 1H), 7.78 (s, 1H), 7.9
0 (s, 1H).

Example-3

[0169]

Embedded image

5-bromo-2- {2-chloro-3,5-
Bis (trifluoromethyl) phenylamino} -3-ethyl-6-trifluoromethyl-4 (3H) -pyrimidinone
(0.85 g, 1.64 mmol) in acetonitrile (30 mL) was added potassium carbonate (0.68 g, 4.92 mmol) and 18-crown-6.
-Ether (0.1 g) was added and stirred at room temperature, and crude methyl 1-bromo-1-ethoxyacetate (0.65 g, 3.28 mmol
l) was added, and the mixture was heated and stirred at 60 ° C. for 3 hours. After the completion of the reaction, the solid was separated by filtration, and the filtrate was concentrated under reduced pressure to obtain a crude product.
This was poured into a 1N aqueous hydrochloric acid solution, extracted with ethyl acetate, and the extract was washed with water and saturated saline, and then the solvent was distilled off. The residue is silica gel column (MERCK Kieselgel60,
Purified by 20% AcOEt-Hex) and N- (5-bromo-1-
Ethyl-6-oxo-4-trifluoromethyl-1,6
-Dihydropyrimidin-2-yl) -N- {2-chloro-
White crystals (0.70 g) of methyl 3,5-bis (trifluoromethyl) phenyl diamino (ethoxy) acetate were obtained. Yield: 6
7%; melting point: 89 to 90 ° C .; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ
0.81 (t, J = 7.2Hz, 3H), 1.16 (t, J = 7.2Hz, 3H), 3.77
(s, 3H), 3.7-3.9 (m, 4H), 5.65 (s, 1H), 7.81 (s, 1H),
7.98 (s, 1H).

Example-4

[0172]

Embedded image

2- {2-chloro-3,5-bis (trifluoromethyl) phenylamino} -3-methyl-6-trifluoromethyl-4 (3H) -pyrimidinone (0.05 g, 1.82
mmol) in acetonitrile (20 mL).
(0.75 g, 5.46 mmol) and 18-crown-6-ether
(0.1 g) and stirred at room temperature, to which was added crude ethyl 1-bromo-1-ethoxyacetate (0.76 g, 3.64 mmol), and the mixture was heated with stirring at 60 ° C. for 3 hours. After the completion of the reaction, the solid was separated by filtration, and the filtrate was concentrated under reduced pressure to obtain a crude product. This is 1N
The mixture was poured into a hydrochloric acid aqueous solution, extracted with ethyl acetate, and the extract was washed with water and saturated saline, and the solvent was distilled off. The residue is a silica gel column (Kieselgel60 manufactured by MERCK, 20% AcOEt-Hex)
And purified by N- {2-chloro-3,5-bis (trifluoromethyl) phenyl} -N- (1-methyl-6-oxo-4-trifluoromethyl-1,6-dihydropyrimidine-2- White crystals (0.74 g) of ethyl yl) amino (ethoxy) acetate were obtained. Yield: 71%; Melting point: 124-125 ° C;
¹ H-NMR (CDCl ₃ , TMS, ppm): δ 1.16 (t, J = 7.2 Hz, 3H),
1.26 (t, J = 7.2Hz, 3H), 3.05 (s, 3H), 3.8 and 3.9 (m, 2
H), 4.20 (m, 2H), 5.87 (s, 1H), 6.58 (s, 1H), 7.91 (s,
1H), 7.95 (s, 1H).

Reference Example-1

[0175]

Embedded image

To a solution of methyl methoxyacetate (10.4 g, 0.10 mol) in carbon tetrachloride (200 mL) were added benzoyl peroxide (0.1 g) and NBS (18.7 g, 0.105 mol), and the mixture was heated under reflux for 4 hours. After completion of the reaction, the solid was filtered off and the solvent was distilled off to give a crude 1
Methyl -methoxy-1-bromoacetate (18.0 g) was obtained. This was used for the next reaction without purification. ¹ H-NMR (C
DCl ₃ , TMS, ppm): δ3.59 (s, 3H), 3.87 (s, 3H), 6.02
(s, 1H).

Reference Example-2

[0178]

Embedded image

DM of sodium hydride (1.14 g, 28.6 mmol)
F (20 mL) The suspension was cooled with ice water, and 2-chloro-3,5
-Bis (trifluoromethyl) aniline (6.27 g, 23.8 mmo
l) in DMF (20mL) solution, the reaction temperature does not rise more than 5 ℃
After slowly dropping the mixture, keep the reaction solution at 5 ° C for 1 hour.
Stirred. Furthermore, 2-methylthio-3-propyl-6-to
Fluoromethyl-4 (3H) -pyrimidinone (6.00 g, 2
(3.8 mmol) in DMF (10 mL).
After dropping slowly, remove the cooling bath and remove
Stirred for hours. After completion of the reaction, the reaction solution is diluted with a 1N aqueous hydrochloric acid solution.
(500 mL), and the organic layer and the aqueous layer were separated by filtration. To organic layer
Xane (100 mL) and water (100 mL) were added and the precipitated crystals were separated by filtration.
After drying, 2- {2-chloro-3,5-bis (trifluoro
Methyl) phenyl diamino-3-propyl-6-trif
Fluoromethyl-4 (3H) -pyrimidinone pale yellow solid
(7.88 g) was obtained. Yield: 71%; Melting point: 92-93 ° C;¹H-NMR
 (CDCl _Three, TMS, ppm): δ1.14 (t, J = 7.2Hz, 3H), 1.9 (m,
 2H), 4.1 (m, 2H), 6.51 (s, 1H), 7.64 (br s, 1H), 7.75
(s, 1H), 9.19 (s, 1H).

Reference Example-3

[0181]

Embedded image

DM of sodium hydride (0.95 g, 23.6 mmol)
F (20 mL) The suspension was cooled with ice water, and 2-bromo-3,5
-Bis (trifluoromethyl) aniline (6.00g, 19.7mmo
A solution of l) in DMF (10 mL) was slowly added dropwise so that the temperature of the reaction solution did not rise above 5 ° C., and the mixture was stirred for 1 hour while maintaining the temperature of the reaction solution at 5 ° C. Further, 2-methylthio-3-isopropyl-6
-Trifluoromethyl-4 (3H) -pyrimidinone (5.45
g, 21.6 mol) in DMF (20 mL) was slowly added dropwise so that the reaction solution temperature did not rise above 5 ° C., and the cooling bath was removed, followed by stirring at room temperature for 2 hours. After completion of the reaction, the reaction solution was poured into a 1N aqueous hydrochloric acid solution (500 mL), and the organic layer and the aqueous layer were separated by filtration. Hexane (100 mL) and water (100 mL) were added to the organic layer, and the precipitated crystals were separated by filtration and dried. 2- {2-bromo-3,5-bis (trifluoromethyl) phenyl} amino-3-isopropyl-6
A pale yellow solid of -trifluoromethyl-4 (3H) -pyrimidinone (5.80 g) was obtained. Yield: 57%; mp: 143 ° C.; ¹ H
-NMR (CDCl ₃ , TMS, ppm): δ 1.74 (d, J = 7.5Hz, 6H), 5.
7 (m, 1H), 6.48 (s, 1H), 7.65 (br s, 1H), 7.73 (s, 1H),
9.02 (s, 1H).

Reference Example-4

[0184]

Embedded image

2- (2-bromo-3,5-bis (trifluoromethyl) phenyl} amino-6-trifluoromethyl-3-vinyl-4 (3H) -pyrimidinone (730 mg, 1.47
Sulfuryl chloride (0.12 mL) was added to an acetic acid solution (10 mL) of (mmol), and the mixture was stirred at room temperature for 4 hours. After completion of the reaction, the reaction solution was poured into saturated aqueous sodium hydrogen carbonate (150 mL) and extracted with ethyl acetate (70 mL × 2). The organic layer was washed with saturated aqueous sodium bicarbonate (150 mL) and saturated saline (1
(00 mL) and dried over anhydrous sodium sulfate. After the desiccant was filtered off, the filtrate was concentrated under reduced pressure. The resulting crude product was purified by a silica gel column (Wakogel C-200, ethyl acetate: hexane = 1: 2) to give 2-
(2-Bromo-3,5-bis (trifluoromethyl) phenyl} amino-5-chloro-6-trifluoromethyl-3
A white solid of -vinyl-4 (3H) -pyrimidinone was obtained.
Yield: 69%; Melting point: 140-143 ° C; ¹ H-NMR (CDCl ₃ , TMS,
ppm): δ5.95 (dd, J = 1.4 and 15.9Hz, 1H), 6.15 (dd,
J = 1.4 and 8.1Hz, 1H), 6.74 (dd, J = 8.1 and 15.9Hz, 1
H), 7.74 (s, 1H), 8.28 (br s, 1H), 9.23 (s, 1H).

Reference Example-5

[0187]

Embedded image

2- {2-bromo-3,5-bis (trifluoromethyl) phenyl} amino-6-trifluoromethyl-3-vinyl-4 (3H) -pyrimidinone (2.50 g, 5.04
N-bromosuccinimide (897 mg, 5.04 mmol) was added to a carbon tetrachloride (50 mL) solution of the compound (1 mmol), and the mixture was heated with stirring for 8 hours. After completion of the reaction, a saturated saline solution (100 mL) and ethyl acetate (70 mL) were added to the reaction solution, the organic layer was separated, and the aqueous layer was extracted with ethyl acetate (70 mL). Combine the organic layers and add saturated saline (150
mL) and dried over anhydrous sodium sulfate. After filtering off the desiccant, the filtrate was concentrated under reduced pressure, and the obtained solid was washed with hexane and dried sufficiently to give 5-bromo-2.
A white solid of-{2-bromo-3,5-bis (trifluoromethyl) phenyl} amino-6-trifluoromethyl-3-vinyl-4 (3H) -pyrimidinone was obtained. Yield: 76
%; Melting point: 139 to 141 ° C .; ¹ H-NMR (CDCl ₃ , TMS, ppm):
δ 5.94 (dd J = 1.3 and 15.8Hz, 1H), 6.13 (dd, J = 1.3 an
d 8.3Hz, 1H), 6.75 (dd, J = 8.3 and 15.8Hz, 1H), 7.74
(s, 1H), 8.30 (br s, 1H), 9.23 (s, 1H).

The compounds and physical properties of the present invention which can be produced by the methods exemplified in the above Examples and Reference Examples are illustrated below, but the present invention is not limited to these compounds.

Example 5 (Compound No. 1-1) N- {2-bromo-3,5-bis (trifluoromethyl)
Phenyl} -N- {1-methyl-6-oxo-4-tri
Fluoromethyl-1,6-dihydropyrimidin-2-i
Methyl ruamino (methoxy) acetate; melting point: 123-127
° C;¹H-NMR (CDCl _Three, TMS, ppm): δ3.04 (s, 3H), 3.61
(s, 3H), 3.77 (s, 3H), 5.38 (s, 1H), 6.60 (s, 1H), 7.
75 (s, 1H), 7.94 (s, 1H). Example-6 (Compound No. 1-2) N- {2-bromo-3,5-bis (trifluoromethyl)
Phenyl｝ -N- ｛5-chloro-1-methyl-6-oxo
So-4-trifluoromethyl-1,6-dihydropyrim
Methyl gin-2-yl {amino (methoxy) acetate;
119-120 ° C; ¹H-NMR (CDCl_Three, TMS, ppm): δ3.11 (s,
3H), 3.61 (s, 3H), 3.77 (s, 3H), 5.55 (s, 1H), 7.72
(s, 1H), 7.96 (s, 1H). Example-7 (Compound No. 1-3) N- {2-bromo-3,5-bis (trifluoromethyl)
Phenyl｝ -N- ｛5-bromo-1-methyl-6-oxo
So-4-trifluoromethyl-1,6-dihydropyrim
Methyl gin-2-yl {amino (methoxy) acetate;
131-132 ° C;¹H-NMR (CDCl_Three, TMS, ppm): δ3.11 (s, 3
H), 3.61 (s, 3H), 3.77 (s, 3H), 5.56 (s, 1H), 7.76 (s,
 1H), 7.95 (s, 1H).

Example-8 (Compound No. 1-4) N- {2-chloro-3,5-bis (trifluoromethyl)
Phenyl} -N- {3-methyl-6-oxo-4-tri
Fluoromethyl-1,6-dihydropyrimidin-2-i
Methyl ruamino (methoxy) acetate; melting point: 103 ° C;¹H-N
MR (CDCl_Three, TMS, ppm): δ3.05 (s, 3H), 3.63 (s, 3H),
3.77 (s, 3H), 5.62 (s, 1H), 6.61 (s, 1H), 7.77 (s, 1
H), 7.96 (s, 1H). Example-9 (Compound No. 1-5) N- {2-chloro-3,5-bis (trifluoromethyl)
Phenyl｝ -N- ｛5-chloro-1-methyl-6-oxo
So-4-trifluoromethyl-1,6-dihydropyrim
Methyl gin-2-yl {amino (methoxy) acetate;
118-119 ° C; ¹H-NMR (CDCl_Three, TMS, ppm): δ 3.12 (s,
 3H), 3.63 (s, 3H), 3.78 (s, 3H), 5.58 (s, 1H), 7.77
(s, 1H), 7.97 (s, 1H).

Example-10 (Compound No. 1-6) N- {5-bromo-1-methyl-6-oxo-4-trifluoromethyl-1,6-dihydropyrimidin-2-yl {-N-} Methyl 2-chloro-3,5-bis (trifluoromethyl) phenyl} amino (methoxy) acetate; melting point: 1
25 ° C .; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ3.12 (s, 3H), 3.64
(s, 3H), 3.78 (s, 3H), 5.59 (s, 1H), 7.77 (s, 1H), 7.97
(s, 1H). Example-11 (Compound No. 1-7) N- {2-bromo-3,5-bis (trifluoromethyl)
Methyl phenyl} -N- {1-ethyl-6-oxo-4-trifluoromethyl-1,6-dihydropyrimidin-2-yl} amino- (methoxy) acetate; melting point: 84-87 ° C;
¹ H-NMR (CDCl ₃ , TMS, ppm): δ0.81 (t, J = 7.1Hz, 3H),
3.62 (s, 3H), 3.64-3.88 (m, 2H), 3.77 (s, 3H), 5.43
(s, 1H), 6.62 (s, 1H), 7.69 (s, 1H), 7.95 (s, 1H).

Example-12 (Compound No. 1-8) N- {2-bromo-3,5-bis (trifluoromethyl)
Methyl phenyl} -N- {5-chloro-1-ethyl-6-oxo-4-trifluoromethyl-1,6-dihydropyrimidin-2-yl} amino- (methoxy) acetate; melting point: 93-96 ° C; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 0.83 (t,
J = 7.1Hz, 3H), 3.62 (s, 3H), 3.68-3.99 (m, 2H), 3.7
7 (s, 3H), 5.41 (s, 1H), 7.70 (s, 1H), 7.96 (s, 1H). Example-13 (Compound No. 1-9) N- {2-bromo-3,5- Bis (trifluoromethyl)
Methyl phenyl} -N- {5-bromo-1-ethyl-6-oxo-4-trifluoromethyl-1,6-dihydropyrimidin-2-yl} amino- (methoxy) acetate; melting point: 82-84 ° C; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 0.82 (t,
J = 7.1Hz, 3H), 3.62 (s, 3H), 3.71 to 3.92 (m, 2H), 3.7
7 (s, 3H), 5.42 (s, 1H), 7.71 (s, 1H), 7.96 (s, 1H).

Example-14 (Compound No. 1-10) N- {2-chloro-3,5-bis (trifluoromethyl)
Methyl phenyl {-N- {1-ethyl-6-oxo-4-trifluoromethyl-1,6-dihydropyrimidin-2-yl} amino (methoxy) acetate; melting point: 73-77 ° C; ¹ H
-NMR (CDCl ₃ , TMS, ppm): δ0.79 (t, J = 7.5Hz, 3H), 3.
65 (s, 3H), 3.69-3.88 (m, 2H), 3.77 (s, 3H), 5.46
(s, 1H), 6.62 (s, 1H), 7.73 (d, J = 1.5Hz, 1H), 7.97
(d, J = 1.5 Hz, 1H). Example-15 (Compound No. 1-11) N- {2-chloro-3,5-bis (trifluoromethyl)
Methyl phenyl} -N- {5-chloro-1-ethyl-6-oxo-4-trifluoromethyl-1,6-dihydropyrimidin-2-yl} amino (methoxy) acetate;
53-57 ° C .; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ0.81 (t, J = 7.
5Hz, 3H), 3.65 (s, 3H), 3.69 to 3.96 (m, 2H), 3.78 (s, 3
H), 5.43 (s, 1H), 7.74 (d, J = 1.5Hz, 1H), 7.98 (d, J =
1.5Hz, 1H).

Example 16 (Compound No. 1-12) N- {5-bromo-1-ethyl-6-oxo-4-trifluoromethyl-1,6-dihydropyrimidin-2-yl} -N-} Methyl 2-chloro-3,5-bis (trifluoromethyl) phenyl} amino (methoxy) acetate; melting point: 110-111 ° C .; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 0.80
(t, J = 7.0Hz, 3H), 3.65 (s, 3H), 3.69〜3.99 (m, 2H),
3.78 (s, 3H), 5.44 (s, 1H), 7.75 (d, J = 1.5Hz, 1H), 7.9
8 (d, J = 1.5Hz, 1H). Example-17 (Compound No. 1-13) N- {2-bromo-3,5-bis (trifluoromethyl)
Phenyl} -N- {6-oxo-1-propyl-4-trifluoromethyl-1,6-dihydropyrimidine-2-
Methyl yl @ amino (methoxy) acetate; melting point: 110-111
° C; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 0.69 (t, J = 7.6 Hz, 3
H), 1.0 and 1.4 (m, 2H), 3.6 (m, 2H), 3.62 (s, 3H), 3.
76 (s, 3H), 5.45 (s, 1H,), 6.60 (s, 1H), 7.68 (s, 1H),
7.95 (s, 1H).

Example-18 (Compound No. 1-14) N- {2-bromo-3,5-bis (trifluoromethyl)
Methyl phenyl} -N- {5-chloro-6-oxo-1-propyl-4-trifluoromethyl-1,6-dihydropyrimidin-2-yl} amino (methoxy) acetate; yellow viscous liquid; ¹ H -NMR (CDCl ₃ , TMS, ppm): δ0.71 (t, J =
7.2Hz, 3H), 1.0 and 1.4 (m, 2H), 3.6 (m, 2H), 3.62
(s, 3H), 3.77 (s, 3H), 5.43 (s, 1H), 7.68 (s, 1H), 7.9
6 (s, 1H). Example-19 (Compound No. 1-15) N- {2-bromo-3,5-bis (trifluoromethyl)
Methyl phenyl} -N- {5-bromo-6-oxo-1-propyl-4-trifluoromethyl-1,6-dihydropyrimidin-2-yl} amino (methoxy) acetate; melting point: 45-48 ° C; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ0.70 (t, J
= 7.3Hz, 3H), 0.90-1.12 (m, 1H), 1.26-1.50 (m, 1H),
3.49 to 3.72 (m, 2H), 3.62 (s, 3H), 3.77 (s, 3H), 5.4
3 (s, 1H), 7.69 (d, J = 1.7Hz, 1H), 7.98 (d, J = 1.7Hz, 1
H).

Example-20 (Compound No. 1-16) N- {2-chloro-3,5-bis (trifluoromethyl)
Phenyl} -N- {6-oxo-1-propyl-4-trifluoromethyl-1,6-dihydropyrimidine-2-
Methyl yl @ amino (methoxy) acetate; melting point: 99 ° C .; ¹ HN
MR (CDCl ₃ , TMS, ppm): δ 0.69 (t, J = 7.6 Hz, 3H), 1.0 a
nd1.4 (m, 2H), 3.5 (m, 2H), 3.65 (s, 3H), 3.77 (s, 3
H), 5.45 (s, 1H), 6.62 (s, 1H), 7.71 (s, 1H), 7.97 (s,
1H). Example-21 (Compound No. 1-17) N- {2-chloro-3,5-bis (trifluoromethyl)
Phenyl} -N- {5-chloro-6-oxo-1-propyl-4-trifluoromethyl-1,6-dihydropyrimidin-2-yl} amino (methoxy) acetate; yellow viscous liquid; ¹ H -NMR (CDCl ₃ , TMS, ppm): δ0.70 (t, J =
7.3Hz, 3H), 0.79 ~ 1.04 (m, 1H), 1.33 ~ 1.56 (m, 1H),
3.48 to 3.76 (m, 2H), 3.65 (s, 3H), 3.77 (s, 3H), 5.42
(s, 1H), 7.71 (d, J = 1.5Hz, 1H), 7.98 (d, J = 1.5Hz, 1
H).

Example-22 (Compound No. 1-18) N- {5-bromo-6-oxo-1-propyl-4-trifluoromethyl-1,6-dihydropyrimidine-2-
Methyl yl} -N- {2-chloro-2,5-bis (trifluoromethyl) phenyl} amino (methoxy) acetate; melting point: 80-82 ° C; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ0 .69 (t,
J = 7.3Hz, 3H), 0.80 ~ 1.00 (m, 1H), 1.31 ~ 1.54 (m, 1
H), 3.48-3.76 (m, 2H), 3.65 (s, 3H), 3.77 (s, 3H),
5.43 (s, 1H), 7.72 (d, J = 1.5Hz, 1H), 8.00 (d, J = 1.5Hz,
1H). Example-23 (Compound No. 1-19) N- {2-bromo-3,5-bis (trifluoromethyl)
Phenyl} -N- {1-isopropyl-6-oxo-4
-Trifluoromethyl-1,6-dihydropyrimidine-
Methyl 2-yl {amino (methoxy) acetate; melting point: 84-87
° C .; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ1.03 (d, J = 6.8 Hz, 3
H), 1.28 (d, J = 6.8Hz, 3H), 3.63 (s, 3H), 3.77 (s, 3
H), 4.44 (sep, J = 6.8Hz, 1H), 5.44 (s, 1H), 6.54 (s, 1
H), 7.66 (d, J = 1.7Hz, 1H), 7.94 (d, J = 1.7Hz, 1H).

Example 24 (Compound No. 1-20) N- {2-bromo-3,5-bis (trifluoromethyl)
Phenyl} -N- (5-chloro-1-isopropyl-6
-Oxo-4-trifluoromethyl-1,6-dihydropyrimidin-2-yl) amino (methoxy) acetate;
Melting point: 116-118 ° C; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ1.05
(d, J = 6.8Hz, 3H), 1.30 (d, J = 6.8Hz, 3H), 3.62 (s, 3
H), 3.77 (s, 3H), 4.48 (sep, J = 6.8Hz, 1H), 5.42 (s, 1H
H), 7.67 (d, J = 1.6 Hz, 1H), 7.95 (d, J = 1.6 Hz, 1H). Example-25 (Compound No. 1-21) N- {2-bromo-3,5-bis (Trifluoromethyl)
Phenyl} -N- (5-chloro-1-isopropyl-6
-Oxo-4-trifluoromethyl-1,6-dihydropyrimidin-2-yl) amino (methoxy) acetate;
Melting point: 112-115 ° C; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 1.
04 (d, J = 6.8Hz, 3H), 1.29 (d, J = 6.8Hz, 3H), 3.62 (s, 3
H), 3.77 (s, 3H), 4.46 (sep, J = 6.8Hz, 1H), 5.44 (s, 1H
H), 7.68 (d, J = 1.8Hz, 1H), 7.95 (d, J = 1.8Hz, 1H).

Example 26 (Compound No. 1-22) N- {2-chloro-3,5-bis (trifluoromethyl)
Phenyl} -N- (1-isopropyl-6-oxo-4
-Trifluoromethyl-1,6-dihydropyrimidine-
2-yl) methyl amino (methoxy) acetate; melting point: 69 ° C;
¹ H-NMR (CDCl ₃ , TMS, ppm): δ1.01 and 1.33 (each d, J
= 6.4Hz, total 6H), 3.65 (s, 3H), 3.77 (s, 3H), 4.44
(sep, J = 6.4Hz, 1H), 5.46 (s, 1H), 6.55 (s, 1H), 7.69
(s, 1H), 7.95 (s, 1H). Example 27 (Compound No. 1-23) N- {2-chloro-3,5-bis (trifluoromethyl)
Phenyl} -N- (5-chloro-1-isopropyl-6
-Oxo-4-trifluoromethyl-1,6-dihydropyrimidin-2-yl) amino (methoxy) acetate;
Yellow viscous liquid; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ1.02 a
nd 1.35 (each d, J = 6.2Hz, total 6H), 3.43 (s, 3H), 3.
77 (s, 3H), 4.47 (sep, J = 6.2Hz, 1H), 5.44 (s, 1H), 7.7
0 (s, 1H), 7.96 (s, 1H).

Example 28 (Compound No. 1-24) N- (5-bromo-1-isopropyl-6-oxo-4
-Trifluoromethyl-1,6-dihydropyrimidine-
2-yl) -N- {2-chloro-3,5-bis (trifluoromethyl) phenyl} amino (methoxy) methyl acetate; melting point: 94-96 ° C; ¹ H-NMR (CDCl ₃ , TMS, ppm) : Δ1.0
2 (d, J = 6.8Hz, 3H), 1.34 (d, J = 6.8Hz, 3H), 3.64 (s, 3
H), 3.77 (s, 3H), 4.46 (sep, J = 6.8Hz, 1H), 5.45 (s, 1H
H), 7.71 (d, J = 1.5 Hz, 1H), 7.97 (d, J = 1.5 Hz, 1H). Example-29 (Compound No. 1-25) N- (1-allyl-6-oxo-4) -Trifluoromethyl-1,6-dihydropyrimidin-2-yl) -N-
{2-bromo-3,5-bis (trifluoromethyl) phenyl} amino (methoxy) methyl acetate; yellow viscous liquid;
¹ H-NMR (CDCl ₃ , TMS, ppm): δ3.61 (s, 3H), 3.77 (s, 3
H), 4.42 ~ 4.43 (m, 2H), 4.62 (d, J = 17.4Hz, 1H), 4.73
(d, J = 10.6Hz, 1H), 5.22 to 5.37 (m, 1H), 5.49 (s, 1
H), 6.63 (s, 1H), 7.71 (d, J = 1.6Hz, 1H), 7.88 (d, J = 1.
6Hz, 1H).

Example-30 (Compound No. 1-26) N- (1-allyl-5-chloro-6-oxo-4-trifluoromethyl-1,6-dihydropyrimidin-2-yl) -N- { Methyl 2-bromo-3,5-bis (trifluoromethyl) phenyl} amino (methoxy) acetate; melting point: 93-96 ° C .; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ3.61 (s, 3
H), 3.77 (s, 3H), 4.45 to 4.48 (m, 2H), 4.66 (dd, J = 1.
6 and 17.4Hz, 1H), 4.76 (dd, J = 1.6 and 10.6Hz, 1H),
5.23-5.38 (m, 1H), 5.47 (s, 1H), 7.27 (d, J = 1.7Hz,
1H), 7.89 (d, J = 1.7 Hz, 1H). Example 31 (Compound No. 1-27) N- (1-allyl-5-bromo-6-oxo-4-trifluoromethyl-1,6) -Dihydropyrimidin-2-yl) -N- {2-bromo-3,5-bis (trifluoromethyl) phenyl} amino (methoxy) acetate; melting point: 88-90 ° C; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ3.61 (s,
3H), 3.77 (s, 3H), 4.45 to 4.48 (m, 2H), 4.65 (d, J = 18.
0Hz, 1H), 4.76 (d, J = 11.0Hz, 1H), 5.22-5.37 (m, 1
H), 5.48 (s, 1H), 7.70 (d, J = 1.7Hz, 1H), 7.89 (d, J = 1.
7Hz, 1H).

Example 32 (Compound No. 1-28) N- (1-allyl-6-oxo-4-trifluoromethyl-1,6-dihydropyrimidin-2-yl) -N-
{2-chloro-3,5-bis (trifluoromethyl) phenyl} amino (methoxy) acetate methyl; yellow viscous liquid;
¹ H-NMR (CDCl ₃ , TMS, ppm): δ 3.64 (s, 3H), 3.77 (s, 3
H), 4.4 (m, 2H), 4.7 (m, 2H), 5.3 (m, 1H), 5.52 (s, 1
H), 6.65 (s, 1H), 7.71 (s, 1H), 7.89 (s, 1H). Example 33 (Compound No. 1-29) Methyl 4-trifluoromethyl-1,6-dihydropyrimidin-2-yl) -N- {2-chloro-3,5-bis (trifluoromethyl) phenyl} amino (methoxy) acetate; melting point: 82-84 ° C ¹ H-NMR (CDCl ₃ , TMS, ppm): δ3.64 (s,
3H), 3.77 (s, 3H), 4.40〜4.50 (m, 2H), 4.65 (d, J = 17.
4Hz, 1H), 4.77 (d, J = 10.6Hz, 1H), 5.22-5.38 (m, 1
H), 5.45 (s, 1H), 7.71 (d, J = 1.8Hz, 1H), 7.91 (d, J =
1.8Hz, 1H).

Example 34 (Compound No. 1-30) N- (1-allyl-5-bromo-6-oxo-4-trifluoromethyl-1,6-dihydropyrimidin-2-yl) -N- ｛ Methyl 2-chloro-3,5-bis (trifluoromethyl) phenyl} amino (methoxy) acetate; melting point: 8
1-83 ° C; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 3.64 (s, 3H), 3.
77 (s, 3H), 4.38-4.48 (m, 2H), 4.65 (d, J = 17.4Hz, 1
H), 4.76 (d, J = 10.5Hz, 1H), 5.22-5.37 (m, 1H), 5.51
(s, 1H), 7.72 (d, J = 1.7Hz, 1H), 7.91 (d, J = 1.7Hz, 1
H). Example-35 (Compound No. 1-31) N- {2-bromo-3,5-bis (trifluoromethyl)
Phenyl} -N- (1-butyl-6-oxo-4-trifluoromethyl-1,6-dihydropyrimidin-2-yl) amino (methoxy) acetate; yellow viscous liquid; ¹ H
-NMR (CDCl ₃ , TMS, ppm): δ0.75 (t, J = 7.2Hz, 3H), 0.8
and 1.3 (m, 2H), 1.1 (m, 2H), 3.6 (m, 2H), 3.62 (s, 3
H), 3.76 (s, 3H), 5.46 (s, 1H), 6.60 (s, 1H), 7.69 (s,
1H), 7.95 (s, 1H).

Example 36 (Compound No. 1-32) N- {2-bromo-3,5-bis (trifluoromethyl)
Methyl phenyl {-N- (5-chloro-1-butyl-6-oxo-4-trifluoromethyl-1,6-dihydropyrimidin-2-yl) amino (methoxy) acetate;
6-80 ° C; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 0.74 (t, J = 7.0H
(z, 3H), 0.80-1.15 (m, 3H), 1.20-1.40 (m, 1H), 3.
55 〜3.75 (m, 2H), 3.63 (s, 3H), 3.77 (s, 3H), 5.43
(s, 1H), 7.69 (d, J = 1.8Hz, 1H), 7.96 (d, J = 1.8Hz, 1
H). Example-37 (Compound No. 1-33) N- {2-bromo-3,5-bis (trifluoromethyl)
Phenyl} -N- (5-bromo-1-butyl-6-oxo-4-trifluoromethyl-1,6-dihydropyrimidin-2-yl) amino (methoxy) acetate; yellow viscous liquid; melting point: 84-88 ° C; ¹ H-NMR (CDCl ₃ , TMS, ppm):
δ0.74 (t, J = 7.0Hz, 3H), 0.78〜4.40 (m, 4H), 3.53〜
3.78 (m, 2H), 3.62 (s, 3H), 3.76 (s, 3H), 5.45 (s, 1
H), 7.70 (d, J = 1.8Hz, 1H), 7.98 (d, J = 1.8Hz, 1H).

Example 38 (Compound No. 1-34) N- (1-butyl-6-oxo-4-trifluoromethyl-1,6-dihydropyrimidin-2-yl) -N-
{2-chloro-3,5-bis (trifluoromethyl) phenyl} amino (methoxy) acetate methyl; yellow viscous liquid;
¹ H-NMR (CDCl ₃ , TMS, ppm): δ 0.74 (t, J = 7.2 Hz, 3H), 0.9
and 1.4 (m, 2H), 1.1 (m, 2H), 3.6 (m, 2H), 3.65 (s, 3
H), 3.77 (s, 3H), 5.47 (s, 1H), 6.62 (s, 1H), 7.71 (s,
1H), 7.97 (s, 1H). Example-39 (Compound No. 1-35) N- (5-bromo-1-butyl-6-oxo-4-trifluoromethyl-1,6-dihydropyrimidine-2 -Yl) -N- {2-chloro-3,5-bis (trifluoromethyl) phenyl} amino (methoxy) acetate; melting point: 4
3 to 45 ° C; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 0.73 (t, J = 7.5H
z, 3H), 0.72 ~ 0.92 (m, 1H), 0.92 ~ 1.18 (m, 2H), 1.20
~ 1.48 (m, 1H), 3.55 ~ 3.80 (m, 2H), 3.65 (s, 3H), 3.7
7 (s, 3H), 5.45 (s, 1H), 7.64 (d, J = 1.5Hz, 1H), 7.96
(d, J = 1.5Hz, 1H).

Example -40 (Compound No. 1-36) N- {2-bromo-3,5-bis (trifluoromethyl)
Phenyl} -N- (1-isobutyl-6-oxo-4-
Trifluoromethyl-1,6-dihydropyrimidine-2
-Yl) methyl amino (methoxy) acetate; yellow viscous liquid; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 0.75 (d, J = 5.6 Hz, 3H),
0.77 (d, J = 5.6Hz, 3H), 2.07 ~ 2.25 (m, 1H), 3.11 ~ 3.2
8 (m, 1H), 3.32 ~ 3.50 (m, 1H), 3.59 (s, 3H), 3.75 (s,
3H), 5.66 (s, 1H), 6.59 (s, 1H), 7.65 (d, J = 1.5Hz, 1H),
7.96 (d, J = 1.5 Hz, 1H). Example-41 (Compound No. 1-37) N- {2-bromo-3,5-bis (trifluoromethyl)
Phenyl} -N- (5-chloro-1-isobutyl-6-
Methyl oxo-4-trifluoromethyl-1,6-dihydropyrimidin-2-yl) amino (methoxy) acetate; melting point: 123-125 ° C .; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 0.75 ( d,
J = 5.3Hz, 3H), 0.78 (d, J = 5.3Hz, 3H), 2.14 (tsep, J = 5.
3 and 7.6Hz, 1H), 3.24 (dd, J = 7.6 and 13.7Hz, 1H),
3.47 (dd, J = 7.6 and 13.7Hz, 1H), 3.59 (s, 3H), 3.75
(s, 3H), 5.61 (s, 1H), 7.64 (d, J = 1.8Hz, 1H), 7.95 (d,
(J = 1.8Hz, 1H)

Example 42 (Compound No. 1-38) N- {2-bromo-3,5-bis (trifluoromethyl)
Phenyl} -N- (5-bromo-1-isobutyl-6-
Methyl oxo-4-trifluoromethyl-1,6-dihydropyrimidin-2-yl) amino (methoxy) acetate; melting point: 138 to 140 ° C .; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 0.75 ( d, J
= 5.1Hz, 3H), 0.78 (d, J = 5.1Hz, 3H), 2.08 (tsep, J = 5.
1 and 7.5Hz, 1H), 3.25 (dd, J = 7.5 and 13.4Hz, 1H),
3.46 (dd, J = 7.5 and 13.4Hz, 1H), 3.59 (s, 3H), 3.75
(s, 3H), 5.62 (s, 1H), 7.65 (d, J = 1.6Hz, 1H), 7.96
(d, J = 1.6 Hz, 1H). Example-43 (Compound No. 1-39) N- {2-chloro-3,5-bis (trifluoromethyl)
Phenyl} -N- (1-isobutyl-6-oxo-4-
Trifluoromethyl-1,6-dihydropyrimidine-2
-Yl) methyl amino (methoxy) acetate; yellow viscous liquid; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 0.76 (dd, J = 6.8 and 1
1.6Hz, 6H), 2.15 (sep, J = 6,8Hz, 1H), 3.2and 3.5 (br,
2H), 3.62 (s, 3H), 3.75 (s, 3H), 5.64 (s, 1H), 6.60
(s, 1H), 7.68 (s, 1H), 7.97 (s, 1H).

Example 44 (Compound No. 1-40) N- {2-chloro-3,5-bis (trifluoromethyl)
Phenyl} -N- (5-chloro-1-isobutyl-6-
Methyl oxo-4-trifluoromethyl-1,6-dihydropyrimidin-2-yl) amino (methoxy) acetate; yellow viscous liquid; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 0.76 (dd , J =
6.4Hz, 11.2Hz, 6H), 2.14 (sep, J = 6,4Hz, 1H), 3.23a
nd 3.53 (m, 2H), 3.63 (s, 3H), 3.82 (s, 3H), 5.58 (s,
1H), 7.67 (s, 1H), 7.98 (s, 1H). Example-45 (Compound No. 1-41) N- (5-bromo-1-isobutyl-6-oxo-4-)
Trifluoromethyl-1,6-dihydropyrimidine-2
-Yl) -N- {2-chloro-3,5-bis (trifluoromethyl) phenyl} amino (methoxy) acetate; melting point: 137-140 ° C; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ0.76 (d,
J = 5.3Hz, 3H), 0.78 (d, J = 5.3Hz, 3H), 2.10 (tsep, J = 5.
1 and 7.5Hz, 1H), 3.25 (dd, J = 7.5 and 13.8Hz, 1H),
3.47 (dd, J = 7.5 and 13.8Hz, 1H), 3.59 (s, 3H), 3.75
(s, 3H), 5.61 (s, 1H), 7.64 (d, J = 1.7Hz, 1H), 7.96 (d,
(J = 1.7Hz, 1H).

Example 46 (Compound No. 1-42) N- (1-benzyl-6-oxo-4-trifluoromethyl)
Tyl-1,6-dihydropyrimidin-2-yl) -N-
｛2-bromo-3,5-bis (trifluoromethyl) fe
Methyl nil @ amino (methoxy) acetate; melting point: 96-100
° C;¹H-NMR (CDCl_Three, TMS, ppm): δ3.53 (s, 3H), 3.76 (s,
 3H), 5.00 (d, J = 16.1Hz, 1H), 5.13 (d, J = 16.1Hz, 1
H), 5.36 (s, 1H), 6.62-6.66 (m, 2H), 6.72 (s, 1H),
7.04-7.06 (m, 3H), 7.44-7.48 (m, 2H). Example-47 (Compound No. 1-43) N- (3-benzyl-5-chloro-6-oxo-4-to
Trifluoromethyl-1,6-dihydropyrimidine-2-
Yl) -N- ｛2-bromo-3,5-bis (trifluoro
Methyl) phenyl diamino (methoxy) methyl acetate;
Point: 120-122 ° C; ¹H-NMR (CDCl_Three, TMS, ppm): δ3.54 (s,
 3H), 3.76 (s, 3H), 5.03 (d, J = 16.6Hz, 1H), 5.17 (d,
J = 16.6Hz, 1H), 5.36 (s, 1H), 6.64-6.66 (m, 2H), 7.05
~ 7.07 (m, 3H), 7.45 (br s, 2H).

Example 48 (Compound No. 1-44) N- (1-benzyl-5-bromo-6-oxo-4-trifluoromethyl-1,6-dihydropyrimidine-2-
Yl) -N- {2-chloro-3,5-bis (trifluoromethyl) phenyl} amino (methoxy) methyl acetate; melting point: 108-110 ° C .; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ3 .56 (s,
3H), 3.75 (s, 3H), 4.99 (d, J = 16.0Hz, 1H), 5.20 (d, J
= 16.0Hz, 1H), 5.41 (s, 1H), 6.59-6.70 (m, 2H), 7.01
Example -49 (Compound No. 1-45) N- (1-benzyl-6-oxo-4-trifluoromethyl-1,6-dihydro) -7.10 (m, 3H), 7.44 to 7.53 (m, 2H). Pyrimidin-2-yl) -N-
Methyl {2-chloro-3,5-bis (trifluoromethyl) phenyl} amino (methoxy) acetate; melting point: 97 ° C; ¹ HN
MR (CDCl ₃ , TMS, ppm): δ3.56 (s, 3H), 3.75 (s, 3H), 4.9
and 5.2 (each br s, 2H), 5.42 (s, 1H), 6.65 (br s, 2H
H), 6.73 (s, 1H), 7.05 (br s, 3H), 7.46 (s, 1H), 7.48
(s, 1H).

Example 50 (Compound No. 1-46) N- (1-benzyl-5-chloro-6-oxo-4-trifluoromethyl-1,6-dihydropyrimidine-2-
Yl) -N- {2-chloro-3,5-bis (trifluoromethyl) phenyl} amino (methoxy) methyl acetate; melting point: 129 ° C .; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ3.56 (s, 3
H), 3.75 (s, 3H), 4,99 and 5.20 (each d, J = 16.4Hz, 2
H), 5.40 (s, 1H), 6.64 (m, 2H), 7.06 (m, 3H), 7.47 (s,
1H), 7.48 (s, 1H). Example 51 (Compound No. 1-47) N- {2,4-bis (trifluoromethyl) phenyl}-
N- (1-vinyl-6-oxo-4-trifluoromethyl-1,6-dihydropyrimidin-2-yl) amino (methoxy) acetate; yellow viscous liquid; ¹ H-NMR (CDCl ₃ , T
(MS, ppm): δ 3.49 (s, 3H), 3.74 (br s, 3H), 5.18 (br s,
1H), 5.45 (br s, 1H), 5.7 (br s, 1H), 5.9 (br s, 1
H), 6.49 (br s, 1H), 7.64 (br s, 1H), 7.82 (d, J = 8.4H
z, 1H), 7.93 (s, 1H).

Example 52 (Compound No. 1-48) N- {2,4-bis (trifluoromethyl) phenyl}-
Methyl N- (5-chloro-1-vinyl-6-oxo-4-trifluoromethyl-1,6-dihydropyrimidin-2-yl) amino (methoxy) acetate; melting point: 115 ° C .; ¹ H-NM
R (CDCl ₃ , TMS, ppm): δ3.49 (s, 3H), 3.74 (s, 3H), 5.3,
5.5 and 6.0 (br s, total 3H), 5.71 (s, 1H), 7.63 (br
Example 53 (Compound No. 1-49) N- {2-bromo-3,5-bis (trifluoromethyl)
Phenyl} -N- (5-chloro-1-vinyl-6-oxo-4-trifluoromethyl-1,6-dihydropyrimidin-2-yl) amino (methoxy) acetate; yellow viscous liquid; ¹ H -NMR (CDCl ₃ , TMS, ppm): δ3.57 (s, 3H),
3.78 (s, 3H), 5.15 (d, J = 6.8Hz, 1H), 5.46 (d, J = 15.6H
z, 1H), 5.80 (s, 1H), 5.86 (dd, J = 6.8 and 15.6Hz, 1
H), 7.74 (s, 1H), 7.91 (s, 1H).

Example 54 (Compound No. 1-50) N- {2,4-bis (trifluoromethyl) phenyl}-
N- (6-oxo-1-propyl-4-trifluoromethyl-1,6-dihydropyrimidin-2-yl) amino
(Methoxy) methyl acetate; yellow viscous liquid; ¹ H-NMR (CDC
l ₃ , TMS, ppm): δ0.74 (t, J = 7.2Hz, 3H), 1.3 and 1.
5 (m, 2H), 3.49 (s, 3H), 3.6 (m, 2H), 3.74 (s, 3H), 5.
41 (s, 1H), 6.57 (s, 1H), 7.54 (d, J = 6.3Hz, 1H), 7.86
(d, J = 6.3 Hz, 1H), 8.03 (s, 1H). Example-55 (Compound No. 2-1) N- ｛2-bromo-3,5-bis (trifluoromethyl)
Phenyl}-N-(1-methyl-6-oxo-4-trifluoromethyl-1,6-dihydro-2-yl) amino (methoxy) ethyl acetate; mp: 84 to 87 ° C.; ¹ H-
NMR (CDCl ₃ , TMS, ppm): δ 1.22 (t, J = 7.2 Hz, 3H), 3.07
(s, 3H), 3.60 (s, 3H), 4.13 to 4.27 (m, 2H), 5.66 (s, 1
H), 6.60 (s, 1H), 7.82 (s, 1H), 7.93 (s, 1H).

Example 56 (Compound No. 2-2) N- {2-bromo-3,5-bis (trifluoromethyl)
Ethyl phenyl {-N- (5-chloro-1-methyl-6-oxo-4-trifluoromethyl-1,6-dihydropyrimidin-2-yl) amino (methoxy) acetate; melting point: 9
6-98 ° C; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 1.22 (t, J = 7.2H
z, 3H), 3.14 (s, 3H), 3.60 (s, 3H), 4.11 ~ 4.28 (m, 2
H), 5.62 (s, 1H), 7.81 (s, 1H), 7.94 (s, 1H). Example-57 (Compound No. 2-3) N- {2-bromo-3,5-bis (tri Fluoromethyl)
Phenyl} -N- (5-bromo-1-methyl-6-oxo-4- (trifluoromethyl) pyrimidin-2-yl)
Ethyl amino (methoxy) acetate; melting point: 74-78 ° C; ¹ H-NMR
(CDCl ₃ , TMS, ppm): δ1.22 (t, J = 7.1Hz, 3H), 3.14
(s, 3H), 3.60 (s, 3H), 4.13 to 4.28 (m, 2H), 5.63 (s, 1
H), 7.82 (s, 1H), 7.94 (s, 1H).

Example 58 (Compound No. 2-4) N- {2-chloro-3,5-bis (trifluoromethyl)
Ethyl phenyl} -N- (1-methyl-6-oxo-4-trifluoromethyl-1,6-dihydropyrimidin-2-yl) amino (methoxy) acetate; yellow viscous liquid; ¹ H-
NMR (CDCl ₃ , TMS, ppm): δ 1.26 (t, J = 7.2 Hz, 3H), 3.07
(s, 3H), 3.63 (s, 3H), 4.20 (m, 2H), 5.69 (s, 1H), 6.
63 (s, 1H), 7.82 (s, 1H), 7.95 (s, 1H). Example-59 (Compound No. 2-5) N- {2-chloro-3,5-bis (trifluoromethyl)
Phenyl} -N- (5-chloro-3-methyl-4-oxo-6- (trifluoromethyl) pyrimidin-2-yl)
Ethyl amino (methoxy) acetate; yellow viscous liquid; ¹ H-NMR
(CDCl ₃ , TMS, ppm): δ1.22 (t, J = 6.8Hz, 3H), 3.14 (s,
3H), 3.62 (s, 3H), 4.20 (m, 2H), 5.65 (s, 1H), 7.82
(s, 1H), 7.96 (s, 1H).

Example-60 (Compound No. 2-6) N- (5-bromo-1-methyl-6-oxo-4-trifluoromethyl-1,6-dihydropyrimidin-2-yl) -N- ｛ Ethyl 2-chloro-3,5-bis (trifluoromethyl) phenyl} amino (methoxy) acetate; yellow viscous liquid; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ1.22 (t, J = 7.2
Hz, 3H), 3.14 (s, 3H), 3.63 (s, 3H), 4.2 (m, 2H), 5.6
6- (s, 1H), 7.82 (s, 1H), 7.96 (s, 1H). Example-61 (Compound No. 2-7) N- {2-bromo-3,5-bis (trifluoromethyl)
Ethyl phenyl} -N- (1-ethyl-6-oxo-4-trifluoromethyl-1,6-dihydropyrimidin-2-yl) amino (methoxy) acetate; yellow viscous liquid; ¹ H-
NMR (CDCl ₃ , TMS, ppm): δ 0.84 (t, J = 7.1 Hz, 3H), 1.23
(t, J = 7.2Hz, 3H), 3.62 (s, 3H), 3.65-3.91 (m, 2H),
4.09 〜 4.33 (m, 2H), 5.50 (s, 1H), 6.61 (s, 1H), 7.76
(d, J = 1.7Hz, 1H), 7.94 (d, J = 1.7Hz, 1H).

Example 62 (Compound No. 2-8) N- {2-bromo-3,5-bis (trifluoromethyl)
Ethyl phenyl} -N- (5-chloro-1-ethyl-6-oxo-4-trifluoromethyl-1,6-dihydropyrimidin-2-yl) amino (methoxy) acetate; mp: 9
9-100 ° C; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 0.85 (t, J =
7.0Hz, 3H), 1.23 (t, J = 7.2Hz, 3H), 3.61 (s, 3H), 3.7
2 to 3.93 (m, 2H), 4.09 to 4.33 (m, 2H), 5.46 (s, 1H), 7.
74 (d, J = 1.6 Hz, 1H), 7.95 (d, J = 1.6 Hz, 1H). Example-63 (Compound No. 2-9) N- ｛2-bromo-3,5-bis (trifluoro Methyl)
Ethyl phenyl {-N- (5-bromo-1-ethyl-6-oxo-4-trifluoromethyl-1,6-dihydropyrimidin-2-yl) amino (methoxy) acetate; melting point: 9
6-97 ° C; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 0.84 (t, J = 7.1
Hz, 3H), 1.23 (t, J = 7.2Hz, 3H), 3.61 (s, 3H), 3.70〜
3.95 (m, 2H), 4.10〜4.34 (m, 2H), 5.47 (s, 1H), 7.75
(s, 1H), 7.95 (s, 1H).

Example 64 (Compound No. 2-10) N- {2-chloro-3,5-bis (trifluoromethyl)
Ethyl phenyl} -N- (1-ethyl-6-oxo-4-trifluoromethyl-1,6-dihydropyrimidin-2-yl) amino (methoxy) acetate; yellow viscous liquid; ¹ H-
NMR (CDCl ₃ , TMS, ppm): δ 0.82 (t, J = 7.0 Hz, 3H), 1.23
(t, J = 7.3Hz, 3H), 3.64 (s, 3H), 3.66-3.92 (m, 2H),
4.10 to 4.22 (m, 2H), 5.22 (s, 1H), 6.62 (s, 1H), 7.78
(d, J = 1.3 Hz, 1H), 7.96 (d, J = 1.3 Hz, 1H). Example-65 (Compound No. 2-11) N- {2-chloro-3,5-bis (trifluoromethyl) )
Ethyl phenyl} -N- (5-chloro-1-ethyl-6-oxo-4-trifluoromethyl-1,6-dihydropyrimidin-2-yl) amino (methoxy) acetate; yellow viscous liquid; ¹ H -NMR (CDCl ₃ , TMS, ppm): δ 0.84 (t, J = 7.0
Hz, 3H), 1.24 (t, J = 7.3Hz, 3H), 3.64 (s, 3H), 3.72〜
3.95 (m, 2H), 4.10〜4.33 (m, 2H), 5.46 (s, 1H), 7.79
(d, J = 1.5Hz, 1H), 7.97 (d, J = 1.5Hz, 1H).

Example 66 (Compound No. 2-12) N- (5-bromo-1-ethyl-6-oxo-4-trifluoromethyl-1,6-dihydropyrimidin-2-yl) -N- { Ethyl 2-chloro-3,5-bis (trifluoromethyl) phenyl {amino (methoxy) acetate;
4 to 58 ° C; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 0.82 (t, J = 7.0
Hz, 3H), 1.24 (t, J = 7.0Hz, 3H), 3.64 (s, 3H), 3.71〜
3.95 (m, 2H), 4.08〜4.36 (m, 2H), 5.50 (s, 1H), 7.80
(d, J = 1.5 Hz, 1H), 8.00 (d, J = 1.5 Hz, 1H). Example-67 (Compound No. 2-13) N- ｛2-bromo-3,5-bis (trifluoromethyl )
Phenyl} -N- (6-oxo-1-propyl-4-trifluoromethyl-1,6-dihydropyrimidine-2-
Yl) amino (methoxy) ethyl acetate; melting point: 95-96 ° C; ¹
H-NMR (CDCl ₃ , TMS, ppm): δ0.73 (t, J = 7.4Hz, 3H),
0.96 to 1.15 (m, 1H), 1.23 (t, J = 7.2Hz, 3H), 1.25 to 1.4
9 (m, 1H), 3.46 to 3.69 (m, 2H), 3.61 (s, 3H), 3.99 to 4.
31 (m, 2H), 5.51 (s, 1H), 6.61 (s, 1H), 7.72 (s, 1H), 7.
94 (s, 1H).

Example -68 (Compound No. 2-14) N- {2-bromo-3,5-bis (trifluoromethyl)
Ethyl phenyl} -N- (5-chloro-6-oxo-1-propyl-4-trifluoromethyl-1,6-dihydropyrimidin-2-yl) amino (methoxy) acetate; melting point: 82-84 ° C; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 0.71 (t,
J = 7.4Hz, 3H), 0.95-1.15 (m, 1H), 1.23 (t, J = 7.2H
z, 3H), 1.29-1.49 (m, 1H), 3.52-3.74 (m, 2H), 3.61
(s, 3H), 4.08 to 4.32 (m, 2H), 5.47 (s, 1H), 7.72 (s, 1
H), 7.95 (s, 1H). Example-69 (Compound No. 2-15) N- {2-bromo-3,5-bis (trifluoromethyl)
Ethyl phenyl} -N- (5-bromo-6-oxo-1-propyl-4-trifluoromethyl-1,6-dihydropyrimidin-2-yl) amino (methoxy) acetate; melting point: 77-81 ° C; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 0.70 (t,
J = 7.4Hz, 3H), 0.95 ~ 1.15 (m, 1H), 1.23 (t, J = 7.1Hz,
3H), 1.25 to 1.45 (m, 1H), 3.52 to 3.74 (m, 2H), 3.61 (s,
3H), 4.09 ~ 4.32 (m, 2H), 5.49 (s, 1H), 7.73 (s, 1H),
7.96 (s, 1H).

Example 70 (Compound No. 2-16) N- {2-chloro-3,5-bis (trifluoromethyl)
Phenyl} -N- (6-oxo-1-propyl-4-trifluoromethyl-1,6-dihydropyrimidine-2-
Yl) amino (methoxy) ethyl acetate; melting point: 75-78 ° C; ¹
H-NMR (CDCl ₃ , TMS, ppm): δ 0.69 (t, J = 7.4 Hz, 3H),
0.86 to 1.09 (m, 1H), 1.23 (t, J = 7.2Hz, 3H), 1.29 to 1.
49 (m, 1H), 3.48 to 3.70 (m, 2H), 3.64 (s, 3H), 4.10 to 4.
32 (m, 2H), 5.51 (s, 1H), 6.62 (s, 1H), 7.75 (s, 1H), 7.
96 (s, 1H). Example-71 (Compound No. 2-17) N- {2-chloro-3,5-bis (trifluoromethyl)
Ethyl phenyl} -N- (5-chloro-6-oxo-1-propyl-4-trifluoromethyl-1,6-dihydropyrimidin-2-yl) amino (methoxy) acetate; yellow viscous liquid; ¹ H -NMR (CDCl ₃ , TMS, ppm): δ0.70 (t, J =
7.4Hz, 3H), 0.86-1.10 (m, 1H), 1.24 (t, J = 7.1Hz, 3
H), 1.35 to 1.50 (m, 1H), 3.52 to 3.76 (m, 2H), 3.64 (s,
3H), 4.10 ~ 4.33 (m, 2H), 5.48 (s, 1H), 7.75 (s, 1H),
7.97 (s, 1H).

Example 72 (Compound No. 2-18) N- (5-bromo-6-oxo-1-propyl-4-trifluoromethyl-1,6-dihydropyrimidine-2-
Ethyl) -N- {2-chloro-3,5-bis (trifluoromethyl) phenyl} amino (methoxy) ethyl acetate; yellow viscous liquid; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 0.69 (t, J
= 7.4Hz, 3H), 0.86-1.07 (m, 1H), 1.24 (t, J = 7.2Hz, 3
H), 1.29 ~ 1.43 (m, 1H), 3.52 ~ 3.76 (m, 2H), 3.64 (s, 3
H), 4.10-4.32 (m, 2H), 5.49 (s, 1H), 7.76 (s, 1H),
7.97 (s, 1H). Example-73 (Compound No. 2-19) N- {2-bromo-3,5-bis (trifluoromethyl)
Phenyl} -N- (1-isopropyl-6-oxo-4
-Trifluoromethyl-1,6-dihydropyrimidine-
Ethyl 2-yl) amino (methoxy) acetate; melting point: 89-94
° C; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 1.08 (d, J = 6.8 Hz, 3
H), 1.22 (t, J = 7.2Hz, 3H), 1.27 (d, J = 6.8Hz, 3H), 3.6
1 (s, 3H), 4.10 ~ 4.31 (m, 2H), 4.46 (sep, J = 6.8Hz, 1
H), 5.49 (s, 1H), 6.54 (s, 1H), 7.72 (s, 1H), 7.92 (s,
1H).

Example 74 (Compound No. 2-20) N- {2-bromo-3,5-bis (trifluoromethyl)
Phenyl} -N- (5-chloro-1-isopropyl-6
-Oxo-4-trifluoromethyl-1,6-dihydropyrimidin-2-yl) amino (methoxy) ethyl acetate;
Melting point: 132-133 ° C; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ1.1
1 (d, J = 6.7Hz, 3H), 1.22 (t, J = 7.2Hz, 3H), 1.29 (d, J
= 6.7Hz, 3H), 3.61 (s, 3H), 4.10〜4.33 (m, 2H), 4.50
(sep, J = 6.7Hz, 1H), 5.46 (s, 1H), 7.73 (s, 1H), 7.94
(s, 1H). Example-75 (Compound No. 2-21) N- {2-bromo-3,5-bis (trifluoromethyl)
Phenyl} -N- (5-bromo-1-isopropyl-6
-Oxo-4-trifluoromethyl-1,6-dihydropyrimidin-2-yl) amino (methoxy) ethyl acetate;
Melting point: 119-121 ° C; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ1.1
0 (d, J = 6.7Hz, 3H), 1.22 (t, J = 7.2Hz, 3H), 1.28 (d, J
= 6.7Hz, 3H), 3.60 (s, 3H), 4.09 ~ 4.32 (m, 2H), 4.49
(sep, J = 6.7Hz, 1H), 5.48 (s, 1H), 7.73 (s, 1H), 7.94
(s, 1H).

Example 76 (Compound No. 2-22) N- {2-chloro-3,5-bis (trifluoromethyl)
Phenyl} -N- (1-isopropyl-6-oxo-4
-Trifluoromethyl-1,6-dihydropyrimidine-
2-yl) amino (methoxy) ethyl acetate; melting point: 94-97
° C; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 1.04 (d, J = 6.7 Hz, 3
H), 1.22 (t, J = 7.2Hz, 3H), 1.32 (d, J = 6.7Hz, 3H), 3.6
3 (s, 3H), 4.10 ~ 4.32 (m, 2H), 4.47 (sep, J = 6.7Hz, 1
H), 5.51 (s, 1H), 6.55 (s, 1H), 7.75 (s, 1H), 7.94 (s,
1H). Example-77 (Compound No. 2-23) N- {2-chloro-3,5-bis (trifluoromethyl)
Phenyl} -N- (5-chloro-1-isopropyl-6
-Oxo-4-trifluoromethyl-1,6-dihydropyrimidin-2-yl) amino (methoxy) ethyl acetate;
Melting point: 96-100 ° C; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ1.07
(d, J = 6.7Hz, 3H), 1.23 (t, J = 7.2Hz, 3H), 1.34 (d, J =
6.7Hz, 3H), 3.63 (s, 3H), 4.10〜4.33 (m, 2H), 4.50 (s
ep, J = 6.7Hz, 1H), 5.48 (s, 1H), 7.75 (s, 1H), 7.95
(s, 1H).

Example -78 (Compound No. 2-24) N- (5-bromo-1-isopropyl-6-oxo-4
-Trifluoromethyl-1,6-dihydropyrimidine-
Ethyl 2-yl) -N- {2-chloro-3,5-bis (trifluoromethyl) phenyl} amino (methoxy) acetate;
Melting point: 87-89 ° C; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ1.07
(d, J = 6.7Hz, 3H), 1.23 (t, J = 7.2Hz, 3H), 1.33 (d, J =
6.7Hz, 3H), 3.63 (s, 3H), 4.10〜4.33 (m, 2H), 4.49 (s
ep, J = 6.7Hz, 1H), 5.50 (s, 1H), 7.77 (s, 1H), 7.96
(s, 1H). Example-79 (Compound No. 2-25) N- (1-allyl-6-oxo-4-trifluoromethyl-1,6-dihydropyrimidin-2-yl) -N-
{2-bromo-3,5-bis (trifluoromethyl) phenyl} amino (methoxy) ethyl acetate; yellow viscous liquid;
¹ H-NMR (CDCl ₃ , TMS, ppm): δ1.22 (t, J = 7.2 Hz, 3H),
3.60 (s, 3H), 4.10 to 4.31 (m, 2H), 4.37 to 4.54 (m, 2
H), 4.66 (d, J = 17.5Hz, 1H), 4.76 (d, J = 10.6Hz, 1H),
5.35 (ddt, J = 5.1, 10.6 and 17.5Hz, 1H), 5.57 (s, 1H),
6.63 (s, 1H), 7.77 (s, 1H), 7.87 (s, 1H).

Example -80 (Compound No. 2-26) N- (1-allyl-5-chloro-6-oxo-4-trifluoromethyl-1,6-dihydropyrimidin-2-yl) -N- ｛ Ethyl 2-bromo-3,5-bis (trifluoromethyl) phenyl} amino (methoxy) acetate; melting point: 1
04-106 ° C; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 1.22 (t, J =
7.1Hz, 3H), 3.60 (s, 3H), 4.09 ~ 4.31 (m, 2H), 4.39 ~
4.59 (m, 2H), 4.69 (d, J = 17.5Hz, 1H), 4.79 (d, J = 10.6
Hz, 1H), 5.35 (ddt, J = 5.4, 10.6 and 17.5Hz, 1H), 5.5
Example 81- (Compound No. 2-27) N- (1-allyl-5-bromo-6-oxo-4-tri) 4 (s, 1H), 7.76 (s, 1H), 7.88 (s, 1H). Ethyl fluoromethyl-1,6-dihydropyrimidin-2-yl) -N- {2-bromo-3,5-bis (trifluoromethyl) phenyl} amino (methoxy) acetate; melting point: 9
_{3 to} 95 ° C; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 1.22 (t, J = 7.2H
z, 3H), 3.60 (s, 3H), 3.99 ~ 4.31 (m, 2H), 4.41 ~ 4.58
(m, 2H), 4.69 (d, J = 17.4Hz, 1H), 4.79 (d, J = 10.6Hz, 1
H), 5.35 (ddt, J = 5.3, 10.6 and 17.4Hz, 1H), 5.55 (s,
1H), 7.76 (s, 1H), 7.88 (s, 1H).

Example 82 (Compound No. 2-28) N- (1-allyl-6-oxo-4-trifluoromethyl-1,6-dihydropyrimidin-2-yl) -N-
{2-chloro-3,5-bis (trifluoromethyl) phenyl} amino (methoxy) acetate; yellow viscous liquid;
¹ H-NMR (CDCl ₃ , TMS, ppm): δ1.23 (t, J = 7.2 Hz, 3H),
3.63 (s, 3H), 4.13 ~ 4.28 (m, 2H), 4.34 ~ 4.53 (m, 2
H), 4.63 (d, J = 17.4Hz, 1H), 4.75 (d, J = 10.6Hz, 1H),
5.33 (ddt, J = 5.6, 10.6 and 17.4Hz, 1H), 5.59 (s, 1
H), 6.65 (s, 1H), 7.77 (s, 1H), 7.88 (s, 1H). Example-83 (Compound No. 2-29) Ethyl 4-trifluoromethyl-1,6-dihydropyrimidin-2-yl) -N- {2-chloro-3,5-bis (trifluoromethyl) phenyl} amino (methoxy) acetate; mp: 6
3 to 65 ° C .; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ1.23 (t, J = 7.2
Hz, 3H), 3.62 (s, 3H), 4.08 to 4.33 (m, 2H), 4.37 to 4.57
(m, 2H), 4.67 (d, J = 17.3Hz, 1H), 4.79 (d, J = 10.3Hz,
1H), 5.34 (ddt, J = 5.3, 10.3 and 17.3Hz, 1H), 5.55
(s, 1H), 7.76 (s, 1H), 7.90 (s, 1H).

Example 84 (Compound No. 2-30) N- (1-allyl-5-bromo-6-oxo-4-trifluoromethyl-1,6-dihydropyrimidin-2-yl) -N- ｛ Ethyl 2-chloro-3,5-bis (trifluoromethyl) phenyl} amino (methoxy) acetate;
70-72 ° C; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 1.23 (t, J =
7.2Hz, 3H), 3.62 (s, 3H), 4.11 ~ 4.22 (m, 2H), 4.37 ~
4.57 (m, 2H), 4.67 (d, J = 17.4Hz, 1H), 4.78 (d, J = 10.6
Hz, 1H), 5.34 (ddt, J = 5.3, 10.6 and 17.4Hz, 1H), 5.57
(s, 1H), 7.77 (s, 1H), 7.90 (s, 1H). Example-85 (Compound No. 2-31) N- {2-bromo-3,5-bis (trifluoromethyl)
Ethyl phenyl} -N- (1-butyl-6-oxo-4-trifluoromethyl-1,6-dihydropyrimidin-2-yl) amino (methoxy) acetate; yellow viscous liquid; ¹ H-
NMR (CDCl ₃ , TMS, ppm): δ 0.74 (t, J = 6.9 Hz, 3H), 0.91
~ 1.14 (m, 4H), 1.23 (t, J = 7.2Hz, 3H), 3.50 ~ 3.68 (m,
2H), 3.61 (s, 3H), 4.08-4.30 (m, 2H), 5.52 (s, 1H),
6.60 (s, 1H), 7.73 (s, 1H), 7.94 (s, 1H).

Example -86 (Compound No. 2-32) N- {2-bromo-3,5-bis (trifluoromethyl)
Ethyl phenyl {-N- (1-butyl-5-chloro-6-oxo-4-trifluoromethyl-1,6-dihydropyrimidin-2-yl) amino (methoxy) acetate;
7-78 ° C; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 0.75 (t, J = 6.9H
z, 3H), 0.85-1.20 (m, 4H), 1.23 (t, J = 7.1Hz, 3H),
3.62 (s, 3H), 3.57 ~ 3.77 (m, 2H), 4.09 ~ 4.32 (m, 2
H), 5.49 (s, 1H), 7.74 (s, 1H), 7.95 (s, 1H). Example-87 (Compound No. 2-33) N- {2-bromo-3,5-bis (trifluoro) Methyl)
Ethyl phenyl {-N- (5-bromo-1-butyl-6-oxo-4-trifluoromethyl-1,6-dihydropyrimidin-2-yl) amino (methoxy) acetate;
5 to 56 ° C; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 0.74 (t, J = 6.8H
z, 3H), 0.90-1.13 (m, 4H), 1.23 (t, J = 7.3Hz, 3H),
3.61 (s, 3H), 3.60 ~ 3.77 (m, 2H), 4.08 ~ 4.32 (m, 2H),
5.50 (s, 1H), 7.74 (s, 1H), 7.95 (s, 1H).

Example -88 (Compound No. 2-34) N- (1-butyl-6-oxo-4-trifluoromethyl-1,6-dihydropyrimidin-2-yl) -N-
{2-chloro-3,5-bis (trifluoromethyl) phenyl} amino (methoxy) acetate; yellow viscous liquid;
¹ H-NMR (CDCl ₃ , TMS, ppm): δ 0.74 (t, J = 7.3 Hz, 3H),
0.98 ~ 1.12 (m, 2H), 1.21 ~ 1.35 (m, 2H), 1.23 (t, J = 7.
2Hz, 3H), 3.58-3.69 (m, 2H), 3.64 (s, 3H), 4.11-4.
29 (m, 2H), 5.23 (s, 1H), 6.60 (s, 1H), 7.76 (s, 1H),
7.96 (s, 1H). Example-89 (Compound No. 2-3) N- (1-butyl-5-chloro-6-oxo-4-trifluoromethyl-1,6-dihydropyrimidin-2-yl) -N- {2-chloro-3,5-bis (trifluoromethyl) phenyl} amino (methoxy) ethyl acetate; melting point: 6
9-70 ° C; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 0.74 (t, J = 7.3
Hz, 3H), 0.99 ~ 1.13 (m, 2H), 1.24 (t, J = 7.1Hz, 3H),
1.25 ~ 1.37 (m, 2H), 3.61 ~ 3.74 (m, 2H), 3.64 (s, 3H),
4.11 ~ 4.30 (m, 2H), 5.49 (s, 1H), 7.76 (s, 1H), 7.97
(s, 1H).

Example 90 (Compound No. 2-36) N- (5-bromo-1-butyl-6-oxo-4-trifluoromethyl-1,6-dihydropyrimidin-2-yl) -N- { Ethyl 2-chloro-3,5-bis (trifluoromethyl) phenyl} amino (methoxy) acetate; yellow viscous liquid; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 0.74 (t, J =
7.0Hz, 3H), 0.98-1.12 (m, 2H), 1.20-1.36 (m, 2H),
1.23 (t, J = 7.1Hz, 3H), 3.59〜3.77 (m, 2H), 3.64 (s, 3
H), 4.08-4.30 (m, 2H), 5.51 (s, 1H), 7.76 (s, 1H),
7.97 (s, 1H). Example-91 (Compound No. 2-37) N- {2-bromo-3,5-bis (trifluoromethyl)
Phenyl} -N- (1-isobutyl-6-oxo-4-
Trifluoromethyl-1,6-dihydropyrimidine-2
-Hyl) amino (methoxy) ethyl acetate; yellow viscous liquid; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 0.73 (d, J = 6.4 Hz, 3
H), 0.76 (d, J = 6.4Hz, 3H), 1.22 (t, J = 7.2Hz, 3H), 2.
05 ~ 2.23 (m, 1H), 3.18 ~ 3.42 (m, 2H), 3.59 (s, 3H),
4.08 to 4.32 (m, 2H), 5.77 (s, 1H), 6.58 (s, 1H), 7.71
(s, 1H), 7.94 (s, 1H).

Example -92 (Compound No. 2-38) N- {2-bromo-3,5-bis (trifluoromethyl)
Phenyl} -N- (5-chloro-1-isobutyl-6-
Oxo-4-trifluoromethyl-1,6-dihydropi
Ethyl (limidin-2-yl) amino (methoxy) acetate;
Point: 91-95 ° C;¹H-NMR (CDCl_Three, TMS, ppm): δ0.75 (d,
J = 6.6Hz, 3H), 0.77 (d, J = 6.6Hz, 3H), 1.22 (t, J = 7.1H
z, 3H), 2.01 ~ 2.23 (m, 1H), 3.17 ~ 3.48 (m, 2H), 3.59
(s, 3H), 4.06 to 4.30 (m, 2H), 5.69 (s, 1H), 7.68 (s, 1
H), 7.95 (s, 1H). Example 93 (Compound No. 2-39) N- {2-bromo-3,5-bis (trifluoromethyl)
Phenyl} -N- (5-bromo-1-isobutyl-6-
Oxo-4-trifluoromethyl-1,6-dihydropi
Ethyl (limidin-2-yl) amino (methoxy) acetate;
Point: 111-114 ° C; ¹H-NMR (CDCl_Three, TMS, ppm): δ0.75
(d, J = 6.6Hz, 3H), 0.77 (d, J = 6.6Hz, 3H), 1.22 (t, J =
7.2Hz, 3H), 2.00 ~ 2.24 (m, 1H), 3.17 ~ 3.51 (m, 2H),
 3.59 (s, 3H), 4.08-4.29 (m, 2H), 5.71 (s, 1H), 7.69
(s, 1H), 7.96 (s, 1H).

Example -94 (Compound No. 2-40) N- {2-chloro-3,5-bis (trifluoromethyl)
Phenyl} -N- (1-isobutyl-6-oxo-4-
Trifluoromethyl-1,6-dihydropyrimidine-2
-Yl) amino (methoxy) ethyl acetate; yellow viscous liquid; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 0.74 (d, J = 6.8 Hz, 3
H), 0.77 (d, J = 6.8Hz, 3H), 1.22 (t, J = 7.2Hz, 3H), 2.
15 (sep, J = 6.8Hz, 1H), 3.19 ~ 3.27 (m, 1H), 3.38 ~ 3.47
(m, 1H), 3.62 (s, 3H), 4.13 ~ 4.26 (m, 2H), 5.73 (s, 1
H), 6.59 (s, 1H), 7.73 (s, 1H), 7.96 (s, 1H). Example-95 (Compound No. 2-41) N- {2-chloro-3,5-bis (trifluoro) Methyl)
Phenyl} -N- (5-chloro-1-isobutyl-6-
Oxo-4- (trifluoromethyl) pyrimidin-2-yl) amino (methoxy) ethyl acetate; mp: 64 - 67 ° C.; ¹ H-
NMR (CDCl ₃ , TMS, ppm): δ 0.75 (d, J = 6.9 Hz, 3H), 0.78
(d, J = 6.9Hz, 3H), 1.23 (t, J = 7.2Hz, 3H), 2.15 (sep,
J = 6.9Hz, 1H), 3.23 ~ 3.32 (m, 1H), 3.44 ~ 3.53 (m, 1
H), 3.62 (s, 3H), 4.08〜4.31 (m, 2H), 5.67 (s, 1H), 7.
72 (s, 1H), 7.97 (s, 1H).

Example 96 (Compound No. 2-42) N- (5-bromo-1-isobutyl-6-oxo-4-)
Trifluoromethyl-1,6-dihydropyrimidine-2
-Yl) -N- {2-chloro-3,5-bis (trifluoromethyl) phenyl} amino (methoxy) ethyl acetate; melting point: 98-100 ° C; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 0.75
(d, J = 6.8Hz, 3H), 0.77 (d, J = 6.8Hz, 3H), 1.22 (t, J =
7.1Hz, 3H), 2.14 (sep, J = 6.8Hz, 1H), 3.24 ~ 3.33 (m,
1H), 3.43 to 3.52 (m, 1H), 3.62 (s, 3H), 4.12 to 4.27 (m,
2H), 5.69 (s, 1H), 7.73 (s, 1H), 7.98 (s, 1H). Example-97 (Compound No. 2-43) N- (1-benzyl-6-oxo-4-trifluoro) Methyl-1,6-dihydropyrimidin-2-yl) -N-
{2-bromo-3,5-bis (trifluoromethyl) phenyl} amino (methoxy) ethyl acetate; melting point: 112-117
° C; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 1.23 (t, J = 7.1 Hz, 3
H), 3.52 (s, 3H), 4.09 ~ 4.29 (m, 2H), 4.99 (d, J = 16.2
Hz, 1H), 5.16 (d, J = 16.2Hz, 1H), 5.41 (s, 1H), 6.63
〜6.69 (m, 2H), 6.72 (s, 1H), 7.00〜7.08 (m, 3H), 7.44
(s, 1H), 7.50 (s, 1H).

Example 98 (Compound No. 2-44) N- (1-benzyl-5-chloro-6-oxo-4- (t)
(Trifluoromethyl) pyrimidin-2-yl) -N- ｛2-
Bromo-3,5-bis (trifluoromethyl) phenyl
Ethyl amino (methoxy) acetate; melting point: 134-136 ° C;¹H-
NMR (CDCl_Three, TMS, ppm): δ1.23 (t, J = 7.2Hz, 3H), 3.5
2 (s, 3H), 4.08 ~ 4.30 (m, 2H), 5.03 (d, J = 16.2Hz, 1H),
 5.19 (d, J = 16.2Hz, 1H), 5.39 (s, 1H), 6.61 to 6.71 (m,
 2H), 7.02 to 7.09 (m, 3H), 7.45 (s, 1H), 7.50 (s, 1H). Example-99 (Compound No. 2-45) N- (1-benzyl-5-bromo-6) Oxo-4-to
Trifluoromethyl-1,6-dihydropyrimidine-2-
Yl) -N- ｛2-bromo-3,5-bis (trifluoro
Ethyl (methyl) phenyl} amino (methoxy) acetate;
Point: 120-124 ° C; ¹H-NMR (CDCl_Three, TMS, ppm): δ1.22
(t, J = 7.2Hz, 3H), 3.52 (s, 3H), 4.06-4.28 (m, 2H),
5.03 (d, J = 16.3Hz, 1H), 5.19 (d, J = 16.3Hz, 1H), 5.40
(s, 1H), 6.61 to 6.72 (m, 2H), 7.01 to 7.09 (m, 3H), 7.4
5 (s, 1H), 7.51 (s, 1H).

Example 100 (Compound No. 2-46) N- (1-benzyl-6-oxo-4-trifluoromethyl)
Tyl-1,6-dihydropyrimidin-2-yl) -N-
｛2-chloro-3,5-bis (trifluoromethyl) fe
Ethyl diamino (methoxy) acetate; melting point: 110-113
° C;¹H-NMR (CDCl _Three, TMS, ppm): δ1.22 (t, J = 7.2Hz, 3
H), 3.54 (s, 3H), 4.12 ~ 4.26 (m, 2H), 4.96 (d, J = 16.3
Hz, 1H), 5.18 (d, J = 16.3Hz, 1H), 5.47 (s, 1H), 6.63
〜6.67 (m, 2H), 6.73 (s, 1H), 7.04〜7.07 (m, 3H), 7.4
Example 101 (Compound No. 2-47) N- (1-benzyl-5-chloro-6-oxo-4-to)
Trifluoromethyl-1,6-dihydropyrimidine-2-
Yl) -N- ｛2-chloro-3,5-bis (trifluoro
Ethyl (methyl) phenyl} amino (methoxy) acetate;
Point: 125-127 ° C; ¹H-NMR (CDCl_Three, TMS, ppm): δ1.22
(t, J = 7.2Hz, 3H), 3.54 (s, 3H), 4.12 ~ 4.27 (m, 2H),
4.99 (d, J = 16.3Hz, 1H), 5.21 (d, J = 16.3Hz, 1H), 5.46
(s, 1H), 6.65-6.67 (m, 2H), 7.05-7.08 (m, 3H), 7.4
7 (s, 1H), 7.53 (s, 1H).

Example 102 (Compound No. 2-48) N- (1-benzyl-5-bromo-6-oxo-4-to
Trifluoromethyl-1,6-dihydropyrimidine-2-
Yl) -N- ｛2-chloro-3,5-bis (trifluoro
Ethyl (methyl) phenyl} amino (methoxy) acetate;
Point: 104-108 ° C; ¹H-NMR (CDCl_Three, TMS, ppm): δ1.22
(t, J = 7.2Hz, 3H), 3.54 (s, 3H), 4.12 ~ 4.27 (m, 2H),
4.99 (d, J = 16.0Hz, 1H), 5.21 (d, J = 16.0Hz, 1H), 5.44
(s, 1H), 6.60-6.70 (m, 2H), 7.06-7.08 (m, 3H), 7.4
7 (s, 1H), 7.52 (s, 1H). Example-103 (Compound No. 2-49) N- {1-bromo-3,5-bis (trifluoromethyl)
Phenyl} -N- (1-vinyl-5-chloro-6-oxo
So-4- (trifluoromethyl) pyrimidin-2-yl)
Ethyl amino (methoxy) acetate; yellow viscous liquid;¹H-NMR
 (CDCl_Three, TMS, ppm): δ1.23 (brt, J = 6.8Hz, 3H), 3.57
(br s, 3H), 4.18 (m, 2H), 5.15 (d, J = 7.2Hz, 1H), 5.4
7 (d, J = 16Hz, 1H), 5.88 (s, 1H), 5.89 (dd, J = 7.2 and
16Hz, 1H), 7.78 (s, 1H), 7.90 (s, 1H).

Example 104 (Compound No. 3-1) N- {2-bromo-3,5-bis (trifluoromethyl)
Phenyl}-N-(1-methyl-6-oxo-4-trifluoromethyl-1,6-dihydro-2-yl) amino (ethoxy) acetate; mp: 129-131 ° C.; ¹
H-NMR (CDCl ₃ , TMS, ppm): δ 1.13 (t, J = 7.2 Hz, 3H),
3.02 (s, 3H), 3.6 and 3.8 (m, 2H), 3.74 (s, 3H), 5.76
(s, 1H), 6.57 (s, 1H), 7.83 (s, 1H), 7.94 (s, 1H). Example-105 (Compound No. 3-2) N- {2-bromo-3,5-bis (Trifluoromethyl)
Methyl phenyl} -N- (5-chloro-1-methyl-6-oxo-4-trifluoromethyl-1,6-dihydropyrimidin-2-yl) amino (ethoxy) acetate; melting point: 1
07-109 ° C; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 1.13 (t, J =
6.8Hz, 3H), 3.10 (s, 3H), 3.77 (s, 3H), 3.6-3.9 (m,
2H), 5.75 (s, 1H), 7.83 (s, 1H), 7.95 (s, 1H).

Example 106 (Compound No. 3-3) N- {2-bromo-3,5-bis (trifluoromethyl)
Methyl phenyl} -N- (5-bromo-1-methyl-6-oxo-4-trifluoromethyl-1,6-dihydropyrimidin-2-yl) amino (ethoxy) acetate; melting point: 1
02-104 ° C; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 1.13 (t, J =
7.2Hz, 3H), 3.10 (s, 3H), 3.77 (s, 3H), 3.6-3.9 (m, 2
H), 5.75 (s, 1H), 7.83 (s, 1H), 7.95 (s, 1H). Example-107 (Compound No. 3-4) N- {2-chloro-3,5-bis (trifluoro) Methyl)
Methyl phenyl} -N- (1-methyl-6-oxo-4-trifluoromethyl-1,6-dihydropyrimidin-2-yl) amino (ethoxy) acetate; melting point: 118 DEG-119 DEG C .;
¹ H-NMR (CDCl ₃ , TMS, ppm): δ 1.17 (t, J = 7.2 Hz, 3H),
3.03 (s, 3H), 3.77 (s, 3H), 3.7-3.9 (m, 2H), 5.68 (s,
1H), 6.58 (s, 1H), 7.85 (s, 1H), 7.96 (s, 1H).

Example -108 (Compound No. 3-5) N- {2-chloro-3,5-bis (trifluoromethyl)
Methyl phenyl} -N- (5-chloro-1-methyl-6-oxo-4-trifluoromethyl-1,6-dihydropyrimidin-2-yl) amino (ethoxy) acetate; melting point: 7
7 ° C .; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 1.17 (t, J = 7.2 Hz,
3H), 3.10 (s, 3H), 3.78 (s, 3H), 3.7 to 3.9 (m, 2H),
5.79 (s, 1H), 7.84 (s, 1H), 7.97 (s, 1H). Example-109 (Compound No. 3-6) N- (5-bromo-1-methyl-6oxo-4-trifluoro) Methyl-1,6-dihydropyrimidin-2-yl) -N- {2-chloro-3,5-bis (trifluoromethyl) phenyl} amino (ethoxy) acetate; yellow viscous liquid; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 1.17 (t, J = 7.2H
z, 3H), 3.10 (s, 3H), 3.77 (s, 3H), 3.7-3.9 (m, 2H),
5.80 (s, 1H), 7.84 (s, 1H), 7.97 (s, 1H).

Example 110 (Compound No. 3-7) N- {2-bromo-3,5-bis (trifluoromethyl)
Phenyl} -N- (1-ethyl-6-oxo-4-trifluoromethyl-1,6-dihydropyrimidin-2-yl) amino (ethoxy) acetate; yellow viscous liquid; ¹ H-
NMR (CDCl ₃ , TMS, ppm): δ 0.82 and 0.84 (each t, J = 6.
8Hz, total 3H), 1.12 (each t, J = 6.8Hz, total 3H), 3.
6-3.9 (m, 3H), 3.82 (s, 3H), 4.2 (m, 1H), 5.62 and
5.66 (eachs, total 1H), 6.58 (s, 1H), 7.78 and 7.82
(each s, total 1H), 7.95 (s, 1H). Example-111 (Compound No. 3-8) N- {2-bromo-3,5-bis (trifluoromethyl)
Methyl phenyl} -N- (5-chloro-1-ethyl-6-oxo-4-trifluoromethyl-1,6-dihydropyrimidin-2-yl) amino (ethoxy) acetate; melting point: 1
31 ° C .; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 0.84 (t, J = 7.2 Hz,
3H), 1.12 (t, J = 7.2Hz, 3H), 3.77 (s, 3H), 3.7-3.9
(m, 4H), 5.59 (s, 1H), 7.77 (s, 1H), 7.96 (s, 1H).

Example 112 (Compound No. 3-9) N- {2-bromo-3,5-bis (trifluoromethyl)
Methyl phenyl} -N- (5-bromo-1-ethyl-6-oxo-4-trifluoromethyl-1,6-dihydropyrimidin-2-yl) amino (ethoxy) acetate; melting point: 1
25-127 ° C; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 0.83 (t, J =
7.2Hz, 3H), 1.12 (t, J = 7.2Hz, 3H), 3.77 (s, 3H), 3.6
~ 3.9 (m, 4H), 5.61 (s, 1H), 7.78 (s, 1H), 7.96 (s, 1
H). Example-113 (Compound No. 3-10) N- {2-chloro-3,5-bis (trifluoromethyl)
Phenyl} -N- (1-ethyl-6-oxo-4-trifluoromethyl-1,6-dihydropyrimidin-2-yl) amino (ethoxy) acetate; yellow viscous liquid; ¹ H-
NMR (CDCl ₃ , TMS, ppm): δ 0.80 (t, J = 7.2 Hz, 3H), 1.1
5 (t, J = 7.2Hz, 3H), 3.77 (s, 3H), 3.7-3.9 (m, 4H),
5.67 (s, 1H), 6.59 (s, 1H), 7.97 (s, 1H), 8.10 (s, 1H).

Example 114 (Compound No. 3-11) N- {2-chloro-3,5-bis (trifluoromethyl)
Methyl phenyl} -N- (5-chloro-1-ethyl-6-oxo-4-trifluoromethyl-1,6-dihydropyrimidin-2-yl) amino (ethoxy) acetate; melting point: 1
03 ° C .; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 0.82 (t, J = 7.2 Hz,
3H), 1.16 (t, J = 7.2Hz, 3H), 3.77 (s, 3H), 3.7-3.9
(m, 4H), 5.63 (s, 1H), 7.81 (s, 1H), 7.98 (s, 1H). Example-115 (Compound No. 3-12) N- (5-bromo-1-ethyl-6) -Oxo-4-trifluoromethyl-1,6-dihydropyrimidin-2-yl) -N- {2-chloro-3,5-bis (trifluoromethyl) phenyl} amino (ethoxy) methyl acetate; melting point: 89 9090 ° C .; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ0.81 (t,
J = 7.2Hz, 3H), 1.16 (t, J = 7.2Hz, 3H), 3.77 (s, 3H),
3.7〜3.9 (m, 4H), 5.65 (s, 1H), 7.81 (s, 1H), 7.98 (s,
1H).

Example 116 (Compound No. 3-13) N- {2-bromo-3,5-bis (trifluoromethyl)
Phenyl} -N- (6-oxo-1-propyl-4-trifluoromethyl-1,6-dihydropyrimidine-2-
Yl) methyl amino (ethoxy) acetate; yellow viscous liquid; ¹
H-NMR (CDCl ₃ , TMS, ppm): δ 0.68 (t, J = 6.8 Hz, 3H),
1.1 and 1.3 (each m, total 2H), 1.11 (t, J = 6.8Hz, 3
H), 3.5-3.8 (m, 3H), 3.76 (s, 3H), 4.2 (m, 1H), 5.63
and 5.68 (each s, total 1H), 6.59 (s, 1H), 7.76 and
7.81 (each s, total 1H), 7.96 (s, 1H). Example 117 (Compound No. 3-14) N- ｛2-bromo-3,5-bis (trifluoromethyl)
Phenyl}-N-(5-chloro-6-oxo-1-propyl-4-trifluoromethyl-1,6-dihydro-2-yl) amino (ethoxy) acetate; mp: 111 ° C.; ¹ H- NMR (CDCl ₃ , TMS, ppm): δ 0.69 (t, J =
7.2Hz, 3H), 1.11 (t, J = 7.2Hz, 3H), 1.4 (m, 2H), 3.3 ~
3.4 (m, 2H), 3.76 (s, 3H), 3.6 to 3.9 (m, 2H), 5.60 (s,
1H), 7.75 (s, 1H), 7.96 (s, 1H).

Example -118 (Compound No. 3-15) N- {2-bromo-3,5-bis (trifluoromethyl)
Methyl phenyl} -N- (5-bromo-6-oxo-1-propyl-4-trifluoromethyl-1,6-dihydropyrimidin-2-yl) amino (ethoxy) acetate Melting point: 1
06 ° C .; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ0.68 (t, J = 7.2H
z, 3H), 1.11 (t, J = 7.2Hz, 3H), 1.2-1.4 (m, 2H), 3.6
3.9 (m, 4H), 3.76 (s, 3H), 5.62 (s, 1H), 7.76 (s, 1
H), 7.96 (s, 1H). Example-119 (Compound No. 3-16) N- {2-chloro-3,5-bis (trifluoromethyl)
Phenyl} -N- (6-oxo-1-propyl-4-trifluoromethyl-1,6-dihydropyrimidine-2-
Yl) methyl amino (ethoxy) acetate; yellow viscous liquid; ¹
H-NMR (CDCl ₃ , TMS, ppm): δ0.68 (t, J = 7.4Hz, 3H),
1.03 (m, 1H), 1.15 (t, J = 7.4Hz, 3H), 1.4 (m, 1H), 3.
4, 3.7 to 3.9 (m, 4H), 3.76 (s, 3H), 5.66 (s, 1H), 6.59
(s, 1H), 7.79 (s, 1H), 7.94 (s, 1H).

Example 120 (Compound No. 3-17) N- {2-chloro-3,5-bis (trifluoromethyl)
Methyl phenyl} -N- (5-chloro-1-oxo-6-propyl-4-trifluoromethyl-1,6-dihydropyrimidin-2-yl) amino (ethoxy) acetate; melting point: 73-75 ° C; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ0.69 (t,
J = 7.2Hz, 3H), 1.0 and 1.4 (m, 2H), 1.15 (t, J = 7.2Hz,
3H), 3.5-3.8 (m, 4H), 3.77 (s, 3H), 5.63 (s, 1H), 7.7
9 (s, 1H), 7.98 (s, 1H). Example-121 (Compound No. 3-18) N- (5-bromo-6-oxo-1-propyl-4-trifluoromethyl-1,6- Dihydropyrimidine-2-
Yl) -N- {2-chloro-3,5-bis (trifluoromethyl) phenyl} amino (ethoxy) methyl acetate; melting point: 74-75 ° C; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ0 .68 (t,
J = 7.2Hz, 3H), 1.0 and 1.4 (m, 2H), 1.15 (t, J = 7.2Hz,
3H), 3.5-3.9 (m, 4H), 3.77 (s, 3H), 5.64 (s, 1H),
7.80 (s, 1H), 7.98 (s, 1H).

Example 122 (Compound No. 3-19) N- {2-bromo-3,5-bis (trifluoromethyl)
Phenyl} -N- (1-isopropyl-6-oxo-4
-Trifluoromethyl-1,6-dihydropyrimidine-
Methyl 2-yl) amino (ethoxy) acetate; melting point: 93-95
° C; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ1.05 and 1.09 (each
d, J = 6.8Hz, total 6H), 1.30 (t, J = 6.8Hz, 3H), 3.6,
3.8, 4.2 and 4.4 (each m, total 3H), 3.76 (s, 3H),
5.62 and 5.65 (each s, total 1H), 6.51 (s, 1H), 7.74
and 7.80 (each s, total 1H), 7.93 (s, 1H). Example-123 (Compound No. 3-20) N-2-bromo-3,5-bis (trifluoromethyl) phenyl} -N- ( 5-chloro-1-isopropyl-6-
Methyl oxo-4-trifluoromethyl-1,6-dihydropyrimidin-2-yl) amino (ethoxy) acetate; melting point: 166 ° C .; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ1.07 (d, J =
6.8Hz, 3H), 1.13 (t, J = 7.2Hz, 3H), 1.27 (d, J = 6.8Hz,
3H), 3.6-3.9 (m, 2H), 3.77 (s, 3H), 4.48 (sep, J = 6.
8Hz, 1H), 5.60 (s, 1H), 7.74 (s, 1H), 7.94 (s, 1H).

Example 124 (Compound No. 3-21) N- {2-bromo-3,5-bis (trifluoromethyl)
Phenyl} -N- (5-bromo-1-isopropyl-6
-Oxo-4-trifluoromethyl-1,6-dihydropyrimidin-2-yl) amino (ethoxy) methyl acetate;
Melting point: 156 ° C .; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ1.06 (d,
J = 6.8Hz, 3H), 1.13 (t, J = 7.2Hz, 3H), 1.25 (d, J = 6.8H
z, 3H), 3.6-3.9 (m, 2H), 3.77 (s, 3H), 4.46 (sep, J =
6.8Hz, 1H), 5.62 (s, 1H), 7.74 (s, 1H), 7.94 (s, 1H). Example-125 (Compound No. 3-22) (Trifluoromethyl)
Phenyl} -N- (1-isopropyl-6-oxo-4
-Trifluoromethyl-1,6-dihydropyrimidine-
Methyl 2-yl) amino (ethoxy) acetate; melting point: 84-86
° C; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ1.03 and 1.08 (each
d, J = 6.8Hz, total 3H), 1.17 (t, J = 7.2Hz, 3H), 1.28
and 1.29 (each d, J = 6.8Hz, total 3H), 3.77 (s, 3H),
3.7 ~ 4.2 (m, 2H), 4.20 and 4.44 (sep, J = 6.8Hz, 1H),
5.66 and 5.69 (s, 1H), 6.52 (s, 1H), 7.77 and 7.84
(s, 1H), 7.94 (s, 1H).

Example -126 (Compound No. 3-23) N- {2-chloro-3,5-bis (trifluoromethyl)
Phenyl} -N- (5-chloro-1-isopropyl-6
-Oxo-4-trifluoromethyl-1,6-dihydropyrimidin-2-yl) amino (ethoxy) methyl acetate;
Melting point: 136-137 ° C; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ1.0
5 and 1.32 (each d, J = 6.8Hz, total 6H), 1.17 (t, J =
6.8Hz, 3H), 3.7-3.9 (m, 2H), 3.77 (s, 3H), 4.47 (se
p, J = 6.8Hz, 1H), 5.64 (s, 1H), 7.77 (s, 1H), 7.96 (s,
1H). Example-127 (Compound No. 3-24) N- (5-bromo-1-isopropyl-6-oxo-4)
-Trifluoromethyl-1,6-dihydropyrimidine-
Methyl 2-yl) -N- {2-chloro-3,5-bis (trifluoromethyl) phenyl} amino (ethoxy) acetate;
Melting point: 128-130 ° C; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ1.04
(d, J = 6.8Hz, 3H), 1.17 (t, J = 6.8Hz, 3H), 1.30 (d, J =
6.8Hz, 3H), 3.7-3.9 (m, 2H), 3.77 (s, 3H), 4.46 (se
p, J = 6.8Hz, 1H), 5.66 (s, 1H), 7.78 (s, 1H), 7.96 (s,
1H).

Example 128 (Compound No. 3-25) N- (1-allyl-6-oxo-4-trifluoromethyl-1,6-dihydropyrimidin-2-yl) -N-
Methyl {2-bromo-3,5-bis (trifluoromethyl) phenyl} amino (ethoxy) acetate; yellow viscous liquid;
¹ H-NMR (CDCl ₃ , TMS, ppm): δ 1.13 (t, J = 7.4 Hz, 3H),
3.6, 3.8 and 4.2 (each m, total 2H), 3.76 (s, 3H),
4.4 (m, 2H), 4.6 and 4.7 (each m, total 2H), 5.3 (m,
1H), 5.67 and 5.72 (each s, total 1H), 6.60 (s, 1H),
7.77 and 7.83 (seach s, total 1H), 7.88 (s, 1H). Example-129 (Compound No. 3-26) N- (1-allyl-5-chloro-6-oxo-4-trifluoromethyl- Methyl 1,6-dihydropyrimidin-2-yl) -N- {2-bromo-3,5-bis (trifluoromethyl) phenyl} amino (ethoxy) acetate;
27 ° C .; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 1.12 (t, J = 6.8 Hz,
3H), 3.6-3.9 (m, 2H), 3.76 (s, 3H), 4.45 (d, J = 5.2H
z, 2H), 4.65 (d, J = 17.6Hz, 1H), 4.77 (d, J = 10.8Hz, 1
H), 5.29 (m, 1H), 5.64 (s, 1H), 7.76 (s, 1H), 7.89 (s,
1H).

Example 130 (Compound No. 3-27) N- (1-allyl-5-bromo-6-oxo-4-trifluoromethyl-1,6-dihydropyrimidin-2-yl) -N- ｛ Methyl 2-bromo-3,5-bis (trifluoromethyl) phenyl} amino (ethoxy) acetate; melting point: 1
24 ° C .; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 1.12 (t, J = 7.2 Hz,
3H), 3.6-3.9 (m, 2H), 3.76 (s, 3H), 4.45 (d, J = 5.2H
z, 2H), 4.64 (d, J = 17.6Hz, 1H), 4.75 (d, J = 10.8Hz, 1
H), 5.29 (m, 1H), 5.65 (s, 1H), 7.77 (s, 1H), 7.89 (s,
1H). Example-131 (Compound No. 3-28) N- (1-allyl-6-oxo-4-trifluoromethyl-1,6-dihydropyrimidin-2-yl) -N-
Methyl {2-chloro-3,5-bis (trifluoromethyl) phenyl} amino (ethoxy) acetate; yellow viscous liquid;
¹ H-NMR (CDCl ₃ , TMS, ppm): δ 1.16 (t, J = 6.8 Hz, 3H),
3.7 to 3.9 (m, 2H), 3.76 (s, 3H), 4.4 (m, 2H), 4.62 (d
d, J = 9.2 and 17.6Hz, 1H), 4.74 (dd, J = 9.2 and 10.2H
z, 1H), 5.3 (m, 1H), 5.73 and 5.77 (each s, total 1
H), 6.61 (s, 1H), 7.80 and 7.85 (each s, total 1H),
7.89 (s, 1H).

Example 132 (Compound No. 3-29) N- (1-allyl-5-chloro-6-oxo-4-trifluoromethyl-1,6-dihydropyrimidin-2-yl) -N- ｛ Methyl 2-chloro-3,5-bis (trifluoromethyl) phenyl} amino (ethoxy) acetate; melting point: 9
2 to 94 ° C; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 1.16 (t, J = 6.8H
z, 3H), 3.7-3.9 (m, 2H), 3.77 (s, 3H), 4.44 (m, 2
H), 4.64 (d, J = 17.6Hz, 1H), 4.76 (d, J = 10.4Hz, 1H),
5.31 (m, 1H), 5.70 (s, 1H), 7.78 (s, 1H), 7.90 (s, 1
H). Example-133 (Compound No. 3-30) N- (1-allyl-5-bromo-6-oxo-4-trifluoromethyl-1,6-dihydropyrimidin-2-yl) -N- ｛ Methyl 2-chloro-3,5-bis (trifluoromethyl) phenyl} amino (ethoxy) acetate; melting point: 9
4 to 95 ° C; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 1.16 (t, J = 6.8H
z, 3H), 3.7-3.9 (m, 2H), 3.77 (s, 3H), 4.44 (m, 2
H), 4.64 (d, J = 17.2Hz, 1H), 4.76 (d, J = 10.8Hz, 1H),
5.30 (m, 1H), 5.71 (s, 1H), 7.79 (s, 1H), 7.90 (s, 1
H).

Example 134 (Compound No. 3-31) N- {3,5-bis (trifluoromethyl) -2- (methylthio) phenyl} -N- (1-methyl-6-oxo-
Methyl 4-trifluoromethyl-1,6-dihydropyrimidin-2-yl) amino (ethoxy) acetate; yellow viscous liquid; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 1.13 (t, J = 6.8Hz,
3H), 3.02 (s, 3H), 3.7-3.9 (m, 2H), 3.77 (s, 3H),
5.77 (s, 1H), 6.57 (s, 1H), 7.83 (s, 1H), 7,94 (s, 1H). Example-135 (Compound No. 4-1) N- {2-bromo-3, 5-bis (trifluoromethyl)
Ethyl phenyl {-N- (1-methyl-6-oxo-4-trifluoromethyl-1,6-dihydropyrimidin-2-yl) amino (ethoxy) acetate; melting point: 128-133
° C; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 1.15 (t, J = 7.0 Hz, 3
H), 1.23 (t, J = 7.1Hz, 3H), 3.05 (s, 3H), 3.60-3.90
(m, 2H), 4.15 to 4.26 (m, 2H), 5.81 (s, 1H), 6.57 (s, 1
H), 7.89 (s, 1H), 7.93 (s, 1H).

Example 136 (Compound No. 4-2) N- {2-bromo-3,5-bis (trifluoromethyl)
Ethyl phenyl} -N- (5-chloro-1-methyl-6-oxo-4-trifluoromethyl-1,6-dihydropyrimidin-2-yl) amino (ethoxy) acetate; mp: 9
4 to 96 ° C; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 1.15 (t, J = 7.0H
z, 3H), 1.23 (t, J = 7.2Hz, 3H), 3.12 (s, 3H), 3.59-3.
71 (m, 1H), 3.78 to 3.90 (m, 1H), 4.15 to 4.27 (m, 2H),
5.77 (s, 1H), 7.88 (s, 1H), 7.94 (s, 1H). Example-137 (Compound No. 4-3) N- {2-bromo-3,5-bis (trifluoromethyl)
Phenyl} -N- (5-bromo-1-methyl-6-oxo-4- (trifluoromethyl) pyrimidin-2-yl)
Ethyl amino (ethoxy) acetate; yellow viscous liquid; ¹ H-NMR
(CDCl ₃ , TMS, ppm): δ1.15 (t, J = 7.0Hz, 3H), 1.23
(t, J = 7.2Hz, 3H), 3.12 (s, 3H), 3.59 ~ 3.71 (m, 1H),
3.78 to 3.87 (m, 1H), 4.15 to 4.27 (m, 2H), 5.79 (s, 1H),
7.88 (s, 1H), 7.94 (s, 1H).

Example 138 (Compound No. 4-4) N- {2-chloro-3,5-bis (trifluoromethyl)
Ethyl phenyl} -N- (1-methyl-6-oxo-4-trifluoromethyl-1,6-dihydropyrimidin-2-yl) amino (ethoxy) acetate; melting point: 124 DEG-125 DEG C .;
¹ H-NMR (CDCl ₃ , TMS, ppm): δ 1.16 (t, J = 7.2 Hz, 3H),
1.26 (t, J = 7.2Hz, 3H), 3.05 (s, 3H), 3.8and 3.9 (m, 2
H), 4.20 (m, 2H), 5.87 (s, 1H), 6.58 (s, 1H), 7.91 (s,
1H), 7.95 (s, 1H). Example-139 (Compound No. 4-5) N- {2-chloro-3,5-bis (trifluoromethyl)
Phenyl} -N- (5-chloro-1-methyl-6-oxo-4- (trifluoromethyl) pyrimidin-2-yl)
Ethyl amino (ethoxy) acetate; yellow viscous liquid; ¹ H-NMR
(CDCl ₃ , TMS, ppm): δ1.18 and 1.24 (each t, J = 7.2H
z, total 6H), 3.12 (s, 3H), 3.8 (m, 2H), 4.2 (m, 2H),
5.83 (s, 1H), 7.90 (s, 1H), 7.96 (s, 1H).

Example 140 (Compound No. 4-6) N- (5-bromo-1-methyl-6-oxo-4-trifluoromethyl-1,6-dihydropyrimidin-2-yl) -N- ｛ Ethyl 2-chloro-3,5-bis (trifluoromethyl) phenyl} amino (ethoxy) acetate; yellow viscous liquid; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 1.18 and 1.2
3 (each t, J = 7.2Hz, total 6H), 3.12 (s, 3H), 3.8 (m, 2
H), 4.2 (m, 2H), 5.84 (s, 1H), 7.90 (s, 1H), 7.96 (s, 1
H). Example-141 (Compound No. 4-7) N- {2-bromo-3,5-bis (trifluoromethyl)
Phenyl}-N-(1-ethyl-6-oxo-4-trifluoromethyl-1,6-dihydro-2-yl) amino (ethoxy) ethyl acetate; yellow viscous liquid; ¹ H-
NMR (CDCl ₃ , TMS, ppm): δ 0.85 (t, J = 7.1 Hz, 3H), 1.1
2 (t, J = 7.0Hz, 3H), 1.24 (t, J = 7.2Hz, 3H), 3.58-3.9
3 (m, 4H), 4.10〜4.31 (m, 2H), 5.66 (s, 1H), 6.58 (s, 1
H), 7.83 (d, J = 1.7Hz, 1H), 7.95 (d, J = 1.7Hz, 1H).

Example 142 (Compound No. 4-8) N- {2-bromo-3,5-bis (trifluoromethyl)
Ethyl phenyl {-N- (5-chloro-1-ethyl-6-oxo-4-trifluoromethyl-1,6-dihydropyrimidin-2-yl) amino (ethoxy) acetate; melting point: 1
17-118 ° C; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 0.86 (t, J
= 7.0Hz, 3H), 1.12 (t, J = 7.0Hz, 3H), 1.24 (t, J = 7.1H
z, 3H), 3.55-3.93 (m, 4H), 4.09-4.31 (m, 2H), 5.62
(s, 1H), 7.81 (s, 1H), 7.95 (s, 1H). Example-143 (Compound No. 4-9) N- {2-bromo-3,5-bis (trifluoromethyl)
Ethyl phenyl {-N- (5-bromo-1-ethyl-6-oxo-4-trifluoromethyl-1,6-dihydropyrimidin-2-yl) amino (ethoxy) acetate; melting point: 1
18-120 ° C; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 0.85 (t, J
= 7.1Hz, 3H), 1.12 (t, J = 7.0Hz, 3H), 1.24 (t, J = 7.2H
z, 3H), 3.55-3.94 (m, 4H), 4.14-4.31 (m, 2H), 5.63
(s, 1H), 7.82 (d, J = 1.7Hz, 1H), 7.95 (d, J = 1.7Hz, 1
H).

Example 144 (Compound No. 4-10) N- {2-chloro-3,5-bis (trifluoromethyl)
Ethyl phenyl} -N- (1-ethyl-6-oxo-4-trifluoromethyl-1,6-dihydropyrimidin-2-yl) amino (ethoxy) acetate; yellow viscous liquid; ¹ H-
NMR (CDCl ₃ , TMS, ppm): δ 0.82 (t, J = 7.0 Hz, 3H), 1.1
6 (t, J = 7.0Hz, 3H), 1.24 (t, J = 7.0Hz, 3H), 3.63-3.93
(m, 4H), 4.11 to 4.31 (m, 2H), 5.70 (s, 1H), 6.59 (s, 1
H), 7.86 (d, J = 1.8 Hz, 1H), 7.96 (d, J = 1.8 Hz, 1H). Example-145 (Compound No. 4-11) N- {2-chloro-3,5-bis (Trifluoromethyl)
Ethyl phenyl {-N- (5-chloro-1-ethyl-6-oxo-4-trifluoromethyl-1,6-dihydropyrimidin-2-yl) amino (ethoxy) acetate; melting point: 9
0-92 ° C; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 0.84 (t, J = 7.0H
z, 3H), 1.16 (t, J = 7.0Hz, 3H), 1.24 (t, J = 7.0Hz, 3
H), 3.67 to 3.97 (m, 4H), 4.11 to 4.32 (m, 2H), 5.66 (s,
1H), 7.84 (d, J = 1.5Hz, 1H), 7.94 (d, J = 1.5Hz, 1H).

Example 146 (Compound No. 4-12) N- (5-bromo-1-ethyl-6-oxo-4-trifluoromethyl-1,6-dihydropyrimidin-2-yl) -N- ｛ Ethyl 2-chloro-3,5-bis (trifluoromethyl) phenyl} amino (ethoxy) acetate; melting point: 93
9797 ° C .; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ0.83 (t, J = 7.0H
z, 3H), 1.16 (t, J = 7.0Hz, 3H), 1.24 (t, J = 7.0Hz, 3H),
3.67 to 3.98 (m, 4H), 4.09 to 4.32 (m, 2H), 5.68 (s, 1H),
7.86 (d, J = 1.8 Hz, 1H), 7.97 (d, J = 1.8 Hz, 1H). Example-147 (Compound No. 4-13) N- ｛2-bromo-3,5-bis (trifluoro Methyl)
Ethyl phenyl} -N- (6-oxo-1-propyl-4- (trifluoromethyl) pyrimidin-2-yl) amino (ethoxy) acetate; colorless viscous liquid: ¹ H-NMR (CDCl ₃ , TM
S, ppm): δ 0.69 (t, J = 7.4Hz, 3H), 1.03 to 1.50 (m, 2
H), 1.11 (t, J = 7.0Hz, 3H), 1.24 (t, J = 7.2Hz, 3H), 3.
38 ~ 3.75 (m, 3H), 3.77 ~ 3.94 (m, 1H), 4.09 ~ 4.31 (m, 2
H), 5.69 (s, 1H), 6.57 (s, 1H), 7.81 (d, J = 1.7Hz, 1H),
7.95 (d, J = 1.7Hz, 1H).

Example 148 (Compound No. 4-14) N- {2-bromo-3,5-bis (trifluoromethyl)
Phenyl} -N- (5-chloro-1-propyl-6-o
Oxo-4-trifluoromethyl-1,6-dihydropyri
(Midin-2-yl) amino (ethoxy) ethyl acetate;
Point: 102-103 ° C; ¹H-NMR (CDCl_Three, TMS, ppm): δ0.69
(t, J = 7.4Hz, 3H), 1.10-1.48 (m, 2H), 1.11 (t, J = 7.1
Hz, 3H), 1.24 (t, J = 7.2Hz, 3H), 3.45-3.93 (m, 4H),
4.09〜4.31 (m, 2H), 5.63 (s, 1H), 7.79 (d, J = 1.8Hz, 1
H), 7.95 (d, J = 1.8 Hz, 1H). Example -149 (Compound No. 4-15) N- {2-bromo-3,5-bis (trifluoromethyl)
Phenyl} -N- (5-bromo-6-oxo-1-pro
Pyr-4-trifluoromethyl-1,6-dihydropyri
(Midin-2-yl) amino (ethoxy) ethyl acetate;
Point: 103-104 ° C; ¹H-NMR (CDCl_Three, TMS, ppm): δ0.69
(t, J = 7.4Hz, 3H), 1.06-1.50 (m, 2H), 1.11 (t, J = 7.0
Hz, 3H), 1.24 (t, J = 7.2Hz, 3H), 3.45〜3.92 (m, 4H),
4.18 to 4.32 (m, 2H), 5.65 (s, 1H), 7.80 (s, 1H), 7.96
(s, 1H).

Example 150 (Compound No. 4-16) N- {2-chloro-3,5-bis (trifluoromethyl)
Phenyl} -N- (6-oxo-1-propyl-4-trifluoromethyl-1,6-dihydropyrimidine-2-
Yl) ethyl amino (ethoxy) acetate; melting point: 73-74 ° C; ¹
H-NMR (CDCl ₃ , TMS, ppm): δ0.68 (t, J = 7.4Hz, 3H),
1.00-1.50 (m, 2H), 1.15 (t, J = 7.0Hz, 3H), 1.24 (t, J
= 7.2Hz, 3H), 3.40〜3.95 (m, 4H), 4.08〜4.32 (m, 2H),
5.71 (s, 1H), 6.59 (s, 1H), 7.84 (d, J = 1.7Hz, 1H),
7.97 (d, J = 1.7 Hz, 1H). Example-151 (Compound No. 4-17) N- ｛2-chloro-3,5-bis (trifluoromethyl)
Ethyl phenyl} -N- (5-chloro-6-oxo-1-propyl-4-trifluoromethyl-1,6-dihydropyrimidin-2-yl) amino (ethoxy) acetate; melting point: 83-84 ° C; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ0.69 (t,
J = 7.4Hz, 3H), 0.98-1.50 (m, 2H), 1.15 (t, J = 7.1Hz,
3H), 1.24 (t, J = 7.2Hz, 3H), 3.47〜3.62 (m, 1H), 3.63
〜3.94 (m, 3H), 4.09〜4.32 (m, 2H), 5.67 (s, 1H), 7.8
3 (d, J = 1.8Hz, 1H), 7.97 (d, J = 1.8Hz, 1H).

Example -152 (Compound No. 4-18) N- (5-bromo-6-oxo-1-propyl-4-trifluoromethyl-1,6-dihydropyrimidine-2-
Ethyl) -N- {2-chloro-3,5-bis (trifluoromethyl) phenyl} amino (ethoxy) ethyl acetate; melting point: 80-82 ° C; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ0 .68 (t,
J = 7.4Hz, 3H), 0.97-1.50 (m, 2H), 1.15 (t, J = 7.0Hz,
3H), 1.24 (t, J = 7.2Hz, 3H), 3.46〜3.94 (m, 4H), 4.09
~ 4.32 (m, 2H), 5.68 (s, 1H), 7.84 (d, J = 1.7Hz, 1H),
7.98 (d, J = 1.7 Hz, 1H). Example-153 (Compound No. 4-19) N- ｛2-bromo-3,5-bis (trifluoromethyl)
Phenyl} -N- (1-isopropyl-6-oxo-4
-Trifluoromethyl-1,6-dihydropyrimidine-
Ethyl 2-yl) amino (ethoxy) acetate; melting point: 98-101
° C; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 1.09 (d, J = 6.9 Hz, 3
H), 1.13 (t, J = 7.0Hz, 3H), 1.23 (t, J = 7.2Hz, 3H), 1.
24 (d, J = 6.6Hz, 3H), 3.56-3.73 (m, 1H), 3.76-3.94
(m, 1H), 4.09 to 4.31 (m, 2H), 4.39 to 4.55 (m, 1H), 5.6
5 (s, 1H), 6.51 (s, 1H), 7.79 (d, J = 1.6Hz, 1H), 7.97
(d, J = 1.6Hz, 1H).

Example 154 (Compound No. 4-20) N- {2-bromo-3,5-bis (trifluoromethyl)
Phenyl} -N- (5-chloro-1-isopropyl-6
-Oxo-4-trifluoromethyl-1,6-dihydropyrimidin-2-yl) amino (ethoxy) ethyl acetate;
Melting point: 148-150 ° C; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ1.1
1 (d, J = 6.7Hz, 3H), 1.14 (t, J = 7.1Hz, 3H), 1.23 (t, J =
7.2Hz, 3H), 1.27 (d, J = 6.6Hz, 3H), 3.56-3.72 (m, 1
H), 3.76-3.91 (m, 1H), 4.08-4.33 (m, 2H), 4.41-4.
Example 59-m (1H), 5.61 (s, 1H), 7.79 (s, 1H), 7.93 (s, 1H). Bis (trifluoromethyl)
Phenyl} -N- (5-bromo-1-isopropyl-6
-Oxo-4-trifluoromethyl-1,6-dihydropyrimidin-2-yl) amino (ethoxy) ethyl acetate;
Melting point: 145-146 ° C; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 1.10
(d, J = 6.7Hz, 3H), 1.13 (t, J = 7.0Hz, 3H), 1.23 (t, J =
7.2Hz, 3H), 1.25 (d, J = 6.7Hz, 3H), 3.56-3.71 (m, 1
H), 3.76-3.92 (m, 1H), 4.08-4.32 (m, 2H), 4.39-4.
59 (m, 1H), 5.63 (s, 1H), 7.80 (d, J = 1.7Hz, 1H), 7.94
(d, J = 1.7Hz, 1H).

Example 156 (Compound No. 4-22) N- {2-chloro-3,5-bis (trifluoromethyl)
Phenyl} -N- (1-isopropyl-6-oxo-4
-(Trifluoromethyl) pyrimidin-2-yl) amino
(Ethoxy) ethyl acetate; melting point: 79-81 ° C .; ¹ H-NMR (CDCl
₃ , TMS, ppm): δ1.08 (d, J = 6.8Hz, 3H), 1.17 (t, J = 7.
0Hz, 3H), 1.23 (t, J = 7.2Hz, 3H), 1.29 (d, J = 6.8Hz, 3
H), 3.64-3.93 (m, 2H), 4.10-4.32 (m, 2H), 4.36-4.
56 (m, 1H), 5.70 (s, 1H), 6.52 (s, 1H), 7.84 (s, 1H),
7.97 (s, 1H). Example -157 (Compound No. 4-23) N- {2-chloro-3,5-bis (trifluoromethyl)
Phenyl} -N- (5-chloro-1-isopropyl-6
-Oxo-4-trifluoromethyl-1,6-dihydropyrimidin-2-yl) amino (ethoxy) ethyl acetate;
Melting point: 128-130 ° C; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 1.09
(d, J = 6.7Hz, 3H), 1.18 (t, J = 7.0Hz, 3H), 1.23 (t, J =
7.2Hz, 3H), 1.31 (d, J = 6.7Hz, 3H), 3.62 to 3.92 (m, 2
H), 4.10 ~ 4.33 (m, 2H), 4.41 ~ 4.60 (m, 1H), 5.66 (s,
1H), 7.83 (s, 1H), 7.95 (s, 1H).

Example -158 (Compound No. 4-24) N- (5-bromo-1-isopropyl-6-oxo-4
-Trifluoromethyl-1,6-dihydropyrimidine-
Ethyl 2-yl) -N- {2-chloro-3,5-bis (trifluoromethyl) phenyl} amino (ethoxy) acetate;
Melting point: 123-124 ° C; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 1.09
(d, J = 6.7Hz, 3H), 1.17 (t, J = 7.0Hz, 3H), 1.23 (t, J =
7.2Hz, 3H), 1.29 (d, J = 6.7Hz, 3H), 3.63-3.92 (m, 2
H), 4.10 ~ 4.33 (m, 2H), 4.40 ~ 4.58 (m, 1H), 5.68 (s,
1H), 7.84 (d, J = 1.8 Hz, 1H), 7.95 (d, J = 1.8 Hz, 1H). Example-159 (Compound No. 4-25) N- (1-allyl-6-oxo-4) -Trifluoromethyl-1,6-dihydropyrimidin-2-yl) -N-
{2-bromo-3,5-bis (trifluoromethyl) phenyl} amino (ethoxy) ethyl acetate; melting point: 58-60 ° C;
¹ H-NMR (CDCl ₃ , TMS, ppm): δ 1.13 (t, J = 7.0 Hz, 3H),
1.23 (t, J = 7.2Hz, 3H), 3.55-3.73 (m, 1H), 3.74-3.91
(m, 1H), 4.08 to 4.32 (m, 2H), 4.45 to 4.50 (m, 2H), 4.6
5 (d, J = 17.4Hz, 1H), 4.76 (d, J = 10.6Hz, 1H), 5.22-5.
45 (m, 1H), 5.71 (s, 1H), 6.60 (s, 1H), 7.83 (s, 1H),
7.87 (s, 1H).

Example 160 (Compound No. 4-26) N- (1-allyl-5-chloro-6-oxo-4-trifluoromethyl-1,6-dihydropyrimidin-2-yl) -N- ｛ Ethyl 2-bromo-3,5-bis (trifluoromethyl) phenyl} amino (ethoxy) acetate; melting point: 1
17-118 ° C; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 1.13 (t, J =
7.1Hz, 3H), 1.23 (t, J = 7.1Hz, 3H), 3.55-3.73 (m, 1
H), 3.74 to 3.92 (m, 1H), 4.09 to 4.31 (m, 2H), 4.41 to 4.
53 (m, 2H), 4.69 (d, J = 17.4Hz, 1H), 4.80 (d, J = 10.6Hz,
1H), 5.25 to 5.45 (m, 1H), 5.68 (s, 1H), 7.82 (s, 1H),
7.88 (s, 1H). Example-161 (Compound No. 4-27) N- (1-allyl-5-bromo-6-oxo-4-trifluoromethyl-1,6-dihydropyrimidin-2-yl) -N- {2-bromo-3,5-bis (trifluoromethyl) phenyl} amino (ethoxy) ethyl acetate; melting point: 1
09-111 ° C; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 1.13 (t, J =
7.0Hz, 3H), 1.23 (t, J = 7.2Hz, 3H), 3.52-3.72 (m, 1
H), 3.74 to 3.92 (m, 1H), 4.06 to 4.30 (m, 2H), 4.38 to 4.
55 (m, 2H), 4.68 (d, J = 17.3Hz, 1H), 4.79 (d, J = 10.6Hz,
1H), 5.21 to 5.46 (m, 1H), 5.69 (s, 1H), 7.82 (s, 1H),
7.88 (s, 1H).

Example 162 (Compound No. 4-28) N- (1-allyl-6-oxo-4-trifluoromethyl-1,6-dihydropyrimidin-2-yl) -N-
{Ethyl 2-chloro-3,5-bis (trifluoromethyl) phenyl} amino (ethoxy) acetate; melting point: 89-90 ° C;
¹ H-NMR (CDCl ₃ , TMS, ppm): δ 1.16 (t, J = 7.0 Hz, 3H),
1.23 (t, J = 7.2Hz, 3H), 3.65-3.92 (m, 2H), 4.08-4.30
(m, 2H), 4.37 to 4.46 (m, 2H), 4.63 (d, J = 17.4Hz, 1H),
4.75 (d, J = 10.6Hz, 1H), 5.22-5.42 (m, 1H), 5.77 (s,
1H), 6.61 (s, 1H), 7.85 (s, 1H), 7.88 (s, 1H). Example-163 (Compound No. 4-29) Ethyl 4-trifluoromethyl-1,6-dihydropyrimidin-2-yl) -N- {2-chloro-3,5-bis (trifluoromethyl) phenyl} amino (ethoxy) acetate; mp: 9
2 to 94 ° C .; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 1.17 (t, J = 7.0
Hz, 3H), 1.23 (t, J = 7.2Hz, 3H), 3.63-3.94 (m, 2H),
4.09 to 4.32 (m, 2H), 4.39 to 4.51 (m, 2H), 4.67 (d, J = 1
7.4Hz, 1H), 4.79 (d, J = 10.6Hz, 1H), 5.23-5.46 (m, 1
H), 5.73 (s, 1H), 7.84 (s, 1H), 7.90 (s, 1H).

Example 164 (Compound No. 4-30) N- (1-allyl-5-bromo-6-oxo-4-trifluoromethyl-1,6-dihydropyrimidin-2-yl) -N- ｛ Ethyl 2-chloro-3,5-bis (trifluoromethyl) phenyl} amino (ethoxy) acetate; melting point: 8
7-89 ° C; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 1.17 (t, J = 7.1
Hz, 3H), 1.23 (t, J = 7.2Hz, 3H), 3.63-3.92 (m, 2H),
4.09 to 4.32 (m, 2H), 4.36 to 4.55 (m, 2H), 4.66 (d, J = 1
7.3Hz, 1H), 4.78 (d, J = 10.6Hz, 1H), 5.22-5.44 (m, 1
H), 5.75 (s, 1H), 7.85 (s, 1H), 7.90 (s, 1H). Example 165 (Compound No. 4-31) N- {2-bromo-3,5-bis (trifluoro) Methyl)
Phenyl}-N-(1-butyl-6-oxo-4-trifluoromethyl-1,6-dihydro-2-yl) amino (ethoxy) ethyl acetate; mp: 52 to 54 ° C.; ¹ H-
NMR (CDCl ₃ , TMS, ppm): δ 0.75 (t, J = 7.2 Hz, 3H), 0.95
~ 1.38 (m, 4H), 1.12 (t, J = 7.0Hz, 3H), 1.23 (t, J = 7.2H
z, 3H), 3.44 to 3.75 (m, 3H), 3.79 to 3.94 (m, 1H), 4.10
~ 4.30 (m, 2H), 5.70 (s, 1H), 6.57 (s, 1H), 7.82 (s, 1
H), 7.94 (s, 1H).

Example 166 (Compound No. 4-32) N- {2-bromo-3,5-bis (trifluoromethyl)
Ethyl phenyl} -N- (11-butyl-5-chloro-6-oxo-4-trifluoromethyl-1,6-dihydropyrimidin-2-yl) amino (ethoxy) acetate; mp: 95-96 ° C; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ0.75 (t,
J = 7.1Hz, 3H), 0.97-1.36 (m, 4H), 1.12 (t, J = 7.0Hz,
3H), 1.23 (t, J = 7.2Hz, 3H), 3.50-3.95 (m, 4H), 4.09
~ 4.32 (m, 2H), 5.66 (s, 1H), 7.80 (s, 1H), 7.95 (s, 1
H). Example-167 (Compound No. 4-33) N- {2-bromo-3,5-bis (trifluoromethyl)
Ethyl phenyl {-N- (1-butyl-5-bromo-6-oxo-4-trifluoromethyl-1,6-dihydropyrimidin-2-yl) amino (ethoxy) acetate; mp: 9
3 to 94 ° C .; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ0.75 (t, J = 7.1
Hz, 3H), 0.93 ~ 1.42 (m, 4H), 1.12 (t, J = 7.0Hz, 3H),
1.24 (t, J = 7.2Hz, 3H), 3.49〜3.95 (m, 4H), 4.07〜4.32
(m, 2H), 5.67 (s, 1H), 7.81 (d, J = 1.5Hz, 1H), 7.95 (d,
(J = 1.5Hz, 1H).

Example 168 (Compound No. 4-34) N- (1-butyl-6-oxo-4-trifluoromethyl-1,6-dihydropyrimidin-2-yl) -N-
{2-chloro-3,5-bis (trifluoromethyl) phenyl} amino (ethoxy) ethyl acetate; yellow viscous liquid;
¹ H-NMR (CDCl ₃ , TMS, ppm): δ 0.75 (t, J = 7.2 Hz, 3H),
0.93 ~ 1.40 (m, 4H), 1.16 (t, J = 7.0Hz, 3H), 1.24 (t, J =
7.2Hz, 3H), 3.48 to 3.95 (m, 4H), 4.09 to 4.32 (m, 2H),
5.74 (s, 1H), 6.58 (s, 1H), 7.86 (d, J = 1.7Hz, 1H), 7.
97 (d, J = 1.7 Hz, 1H). Example-169 (Compound No. 4-35) N- (1-butyl-5-chloro-6-oxo-4-trifluoromethyl-1,6-dihydropyrimidine -2-yl) -N- {2-chloro-3,5-bis (trifluoromethyl) phenyl} amino (ethoxy) ethyl acetate; melting point: 7
3 to 74 ° C .; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ0.75 (t, J = 7.2
Hz, 3H), 0.90 ~ 1.44 (m, 4H), 1.16 (t, J = 7.0Hz, 3H),
1.24 (t, J = 7.2Hz, 3H), 3.50 ~ 3.95 (m, 4H), 4.08 ~ 4.32
(m, 2H), 5.68 (s, 1H), 7.84 (s, 1H), 7.97 (s, 1H).

Example 170 (Compound No. 4-36) N- (1-butyl-5-bromo-6-oxo-4-trifluoromethyl-1,6-dihydropyrimidin-2-yl) -N- { Ethyl 2-chloro-3,5-bis (trifluoromethyl) phenyl} amino (ethoxy) acetate; mp: 6
5 to 66 ° C; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 0.75 (t, J = 7.2
Hz, 3H), 0.93 to 1.43 (m, 4H), 1.17 (t, J = 7.0Hz, 3H),
1.24 (t, J = 7.2Hz, 3H), 3.51 ~ 3.98 (m, 4H), 4.06 ~ 4.
34 (m, 2H), 5.71 (s, 1H), 7.86 (d, J = 1.6Hz, 1H), 7.98
(d, J = 1.6 Hz, 1H). Example-171 (Compound No. 4-37) N- {2-bromo-3,5-bis (trifluoromethyl)
Phenyl} -N- (1-isobutyl-6-oxo-4-
Trifluoromethyl-1,6-dihydropyrimidine-2
-Hyl) amino (ethoxy) ethyl acetate; colorless viscous liquid; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 0.73 (d, J = 6.7 Hz, 3
H), 0.75 (d, J = 6.7Hz, 3H), 1.10 (t, J = 7.0Hz, 3H), 1.
22 (t, J = 7.2Hz, 3H), 2.08-2.28 (m, 1H), 3.02-3.27
(m, 1H), 3.33 to 3.52 (m, 1H), 3.52 to 3.68 (m, 1H), 3.7
7 to 3.93 (m, 1H), 4.10 to 4.27 (m, 2H), 5.92 (s, 1H), 6.5
5 (s, 1H), 7.79 (d, J = 1.7Hz, 1H), 7.94 (d, J = 1.7Hz, 1
H).

Example 172 (Compound No. 4-38) N- {2-bromo-3,5-bis (trifluoromethyl)
Phenyl} -N- (5-chloro-1-isobutyl-6-
Ethyl oxo-4-trifluoromethyl-1,6-dihydropyrimidin-2-yl) amino (ethoxy) acetate; melting point: 95-97 ° C .; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 0.75 (d ,
J = 6.7Hz, 3H), 0.77 (d, J = 6.7Hz, 3H), 1.11 (t, J = 7.0H
z, 3H), 1.23 (t, J = 7.2Hz, 3H), 2.08-2.29 (m, 1H),
3.12 to 3.34 (m, 1H), 3.36 to 3.71 (m, 2H), 3.78 to 3.95
(m, 1H), 4.06 to 4.31 (m, 2H), 5.85 (s, 1H), 7.78 (d, J
= 1.7Hz, 1H), 7.96 (d, J = 1.7Hz, 1H). Example-173 (Compound No. 4-39) N- ｛2-bromo-3,5-bis (trifluoromethyl)
Phenyl} -N- (5-bromo-1-isobutyl-6-
Ethyl oxo-4-trifluoromethyl-1,6-dihydropyrimidin-2-yl) amino (ethoxy) acetate; melting point: 101-102 ° C .; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 0.74
(d, J = 6.7Hz, 3H), 0.75 (d, J = 6.7Hz, 3H), 1.10 (t, J =
7.0Hz, 3H), 1.22 (t, J = 7.2Hz, 3H), 2.06 ~ 2.26 (m, 1
H), 3.12 to 3.32 (m, 1H), 3.38 to 3.67 (m, 2H), 3.78 to 3.
94 (m, 1H), 4.08 ~ 4.30 (m, 2H), 5.85 (s, 1H), 7.78 (s,
1H), 7.95 (s, 1H).

Example 174 (Compound No. 4-40) N- {2-chloro-3,5-bis (trifluoromethyl)
Phenyl} -N- (1-isobutyl-6-oxo-4-
Trifluoromethyl-1,6-dihydropyrimidine-2
-Hyl) amino (ethoxy) ethyl acetate; yellow viscous liquid; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 0.74 (d, J = 6.3 Hz, 3
H), 0.76 (d, J = 6.3Hz, 3H), 1.14 (t, J = 7.0Hz, 3H), 1.
22 (t, J = 7.2Hz, 3H), 2.09 ~ 2.29 (m, 1H), 3.10 ~ 3.29
(m, 1H), 3.37 to 3.54 (m, 1H), 3.61 to 3.76 (m, 1H), 3.8
0 to 3.96 (m, 1H), 4.12 to 4.27 (m, 2H), 5.92 (s, 1H), 6.5
7 (s, 1H), 7.82 (d, J = 1.6Hz, 1H), 7.97 (d, J = 1.6Hz, 1
H). Example-175 (Compound No. 4-41) N- {2-chloro-3,5-bis (trifluoromethyl)
Ethyl phenyl} -N- (5-chloro-1-isobutyl-6oxo-4-trifluoromethyl-1,6-dihydropyrimidin-2-yl) amino (ethoxy) acetate; melting point: 79-81 ° C .; ¹ H -NMR (CDCl ₃ , TMS, ppm): δ0.76 (d,
J = 6.3Hz, 3H), 0.78 (d, J = 6.3Hz, 3H), 1.15 (t, J = 7.0H
z, 3H), 1.24 (t, J = 7.2Hz, 3H), 2.10-2.30 (m, 1H),
3.18 to 3.36 (m, 1H), 3.43 to 3.60 (m, 1H), 3.61 to 3.78
(m, 1H), 3.81 to 3.98 (m, 1H), 4.06 to 4.33 (m, 2H), 5.8
5 (s, 1H), 7.82 (d, J = 1.6Hz, 1H), 7.99 (d, J = 1.6Hz, 1
H).

Example 176 (Compound No. 4-42) N- {2-chloro-3,5-bis (trifluoromethyl)
Phenyl} -N- (5-bromo-1-isobutyl-6-
Oxo-4-trifluoromethyl-1,6-dihydropi
Ethyl limidin-2-yl) amino (ethoxy) acetate;
Point: 89-93 ° C;¹H-NMR (CDCl_Three, TMS, ppm): δ0.75 (d,
J = 6.6Hz, 3H), 0.77 (d, J = 6.6Hz, 3H), 1.14 (t, J = 7.1H
z, 3H), 1.23 (t, J = 7.2Hz, 3H), 2.08-2.28 (m, 1H), 3.
18 ~ 3.35 (m, 1H), 3.43 ~ 3.60 (m, 1H), 3.60 ~ 3.76 (m, 1
H), 3.80 to 3.96 (m, 1H), 4.07 to 4.30 (m, 2H), 5.85 (s,
1H), 7.81 (d, J = 1.7 Hz, 1H), 7.98 (d, J = 1.7 Hz, 1H). Example-177 (Compound No. 4-43) -Trifluorome
Tyl-1,6-dihydropyrimidin-2-yl) -N-
｛2-bromo-3,5-bis (trifluoromethyl) fe
Ethyl nildiamino (ethoxy) acetate; melting point: 117-120
° C;¹H-NMR (CDCl _Three, TMS, ppm): δ1.05 (t, J = 7.0Hz, 3
H), 1.24 (t, J = 7.2Hz, 3H), 3.40 ~ 3.58 (m, 1H), 3.68
~ 3.85 (m, 1H), 4.09 ~ 4.26 (m, 2H), 5.00 (d, J = 16.3H
z, 1H), 5.14 (d, J = 16.3Hz, 1H), 5.59 (s, 1H), 6.58〜
6.70 (m, 2H), 6.68 (s, 1H), 6.88 to 7.10 (m, 3H), 7.45
(s, 1H), 7.57 (s, 1H).

Example 178 (Compound No. 4-44) N- (1-benzyl-5-chloro-6-oxo-4-to)
Trifluoromethyl-1,6-dihydropyrimidine-2-
Yl) -N- ｛2-bromo-3,5-bis (trifluoro
Ethyl (methyl) phenyl} amino (ethoxy) acetate;
Point: 157-159 ° C; ¹H-NMR (CDCl_Three, TMS, ppm): δ1.05
(t, J = 7.0Hz, 3H), 1.24 (t, J = 7.2Hz, 3H), 3.41-3.57
(m, 1H), 3.69-3.84 (m, 1H), 4.09-4.28 (m, 2H), 5.0
0 (d, J = 16.5Hz, 1H), 5.17 (d, J = 16.5Hz, 1H), 5.56 (s,
 1H), 6.61 to 6.72 (m, 2H), 7.02 to 7.11 (m, 3H), 7.47
(s, 1H), 7.56 (s, 1H). Example-179 (Compound No. 4-45) N- (1-benzyl-5-bromo-6-oxo-4-to)
Trifluoromethyl-1,6-dihydropyrimidine-2-
Yl) -N- ｛2-bromo-3,5-bis (trifluoro
Ethyl (methyl) phenyl} amino (ethoxy) acetate;
Point: 151-153 ° C; ¹H-NMR (CDCl_Three, TMS, ppm): δ1.05
(t, J = 7.0Hz, 3H), 1.24 (t, J = 7.2Hz, 3H), 3.40 ~ 3.59
(m, 1H), 3.67-3.86 (m, 1H), 4.07-4.30 (m, 2H), 5.0
0 (d, J = 16.5Hz, 1H), 5.17 (d, J = 16.5Hz, 1H), 5.57 (s,
 1H), 6.60 to 6.72 (m, 2H), 6.98 to 7.12 (m, 3H), 7.47 (s,
 1H), 7.57 (s, 1H).

Example 180 (Compound No. 4-46) N- (1-benzyl-6-oxo-4-trifluoromethyl)
Tyl-1,6-dihydropyrimidin-2-yl) -N-
｛2-chloro-3,5-bis (trifluoromethyl) fe
Ethyl nildiamino (ethoxy) acetate; melting point: 121-122
° C;¹H-NMR (CDCl _Three, TMS, ppm): δ1.09 (t, J = 7.1Hz, 3
H), 1.23 (t, J = 7.2Hz, 3H), 3.47〜3.85 (m, 2H), 4.07
~ 4.31 (m, 2H), 4.93 (d, J = 16.5Hz, 1H), 5.17 (d, J = 1
6.5Hz, 1H), 5.66 (s, 1H), 6.59 to 6.68 (m, 2H), 6.70 (s,
 1H), 7.01 to 7.10 (m, 3H), 7.48 (s, 1H), 7.60 (s, 1H). Example-181 (Compound No. 4-47) N- (1-benzyl-5-chloro-6-) Oxo-4-to
Trifluoromethyl-1,6-dihydropyrimidine-2-
Yl) -N- ｛2-chloro-3,5-bis (trifluoro
Ethyl (methyl) phenyl} amino (ethoxy) acetate;
Point: 143-144 ° C; ¹H-NMR (CDCl_Three, TMS, ppm): δ1.09
(t, J = 7.1Hz, 3H), 1.24 (t, J = 7.2Hz, 3H), 3.48-3.65
(m, 1H), 3.78 to 3.85 (m, 1H), 4.09 to 4.30 (m, 2H), 4.9
7 (d, J = 16.4Hz, 1H), 5.19 (d, J = 16.4Hz, 1H), 5.63 (s,
 1H), 6.58 to 6.74 (m, 2H), 7.01 to 7.13 (m, 3H), 7.49 (s,
 1H), 7.59 (s, 1H).

Example 182 (Compound No. 4-48) N- (1-benzyl-5-bromo-6-oxo-4-to)
Trifluoromethyl-1,6-dihydropyrimidine-2-
Yl) -N- ｛2-chloro-3,5-bis (trifluoro
Ethyl (methyl) phenyl} amino (ethoxy) acetate;
Point: 124-127 ° C; ¹H-NMR (CDCl_Three, TMS, ppm): δ1.09
(t, J = 7.0Hz, 3H), 1.23 (t, J = 7.1Hz, 3H), 3.48 to 3.84
(m, 2H), 4.10-4.30 (m, 2H), 5.00 (d, J = 16.4Hz, 1H),
 5.19 (d, J = 16.4Hz, 1H), 5.64 (s, 1H), 6.59 to 6.71 (m,
2H), 7.01 to 7.12 (m, 3H), 7.49 (s, 1H), 7.60 (s, 1H). Example-183 (Compound No. 4-49) N- {2-bromo-3,5-bis ( (Trifluoromethyl)
Phenyl} -N- (5-bromo-1-vinyl-6-oxo
So-4-trifluoromethyl-1,6-dihydropyrim
Ethyl (2-zinyl) amino (ethoxy) acetate; mp: 9
0 ° C;¹H-NMR (CDCl_Three, TMS, ppm): δ1.32 and 1.38 (eac
h t, J = 7.2Hz, total 6H), 3.8 (m, 2H), 4.26 and 4.36
(q, J = 7.2Hz, 2H), 5.13 (d, J = 8.0Hz, 1H), 5.46 (d, J =
16Hz, 1H), 5.87 (dd, J = 8.0 and 16Hz, 1H), 6.00 (s, 1
H), 7.82 (s, 1H), 7.90 (s, 1H).

Example 184 (Compound No. 5-1) N- {2-bromo-3,5-bis (trifluoromethyl)
Phenyl {-N- (1-ethyl-6-oxo-4-trifluoromethyl-1,6-dihydropyrimidin-2-yl} amino (propyloxy) acetate methyl; yellow viscous liquid; ¹ H-NMR ( CDCl ₃ , TMS, ppm): δ0.83 (t, J = 7.0Hz,
3H), 0.89 (t, J = 7.4Hz, 3H), 1.56-1.70 (m, 2H), 3.6
0 (s, 3H), 3.67 to 3.85 (m, 2H), 4.05 to 4.17 (m, 2H), 5.
Example 185 (Compound No. 5-2) N- {2-bromo-3,5-) 50 (s, 1H), 6.61 (s, 1H), 7.76 (s, 1H), 7.94 (s, 1H). Bis (trifluoromethyl)
Methyl phenyl} -N- (1-ethyl-6-oxo-4-trifluoromethyl-1,6-dihydropyrimidin-2-yl) amino (isopropyloxy) acetate; yellow viscous liquid; ¹ H-NMR ( CDCl ₃ , TMS, ppm): δ0.86 (t, J = 7.0H
z, 3H), 1.15 (d, J = 6.3Hz, 3H), 1.21 (d, J = 6.3Hz, 3H),
3.59 (s, 3H), 3.78 (q, J = 7.0Hz, 2H), 5.03 (sep, J = 6.3
Hz, 1H), 5.56 (s, 1H), 6.61 (s, 1H), 7.80 (s, 1H), 7.9
3 (s, 1H).

Example 186 (Compound No. 5-3) N- {2-bromo-3,5-bis (trifluoromethyl)
Phenyl} -N (1-ethyl-6-oxo-4-trifluoromethyl-1,6-dihydropyrimidin-2-yl) amino (butyloxy) acetate; yellow viscous liquid; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ0.83 (t, J = 7.0Hz, 3
H), 0.90 (t, J = 7.3Hz, 3H), 1.23 ~ 1.35 (m, 2H), 1.52 ~
1.63 (m, 2H), 3.59 (s, 3H), 3.68 ~ 3.85 (m, 2H), 4.09 ~
4,19 (m, 2H), 5.50 (s, 1H), 6.61 (s, 1H), 7.76 (s, 1H),
7.94 (s, 1H). Example-187 (Compound No. 5-4) N- {2-bromo-3,5-bis (trifluoromethyl)
Methyl phenyl} -N- (1-ethyl-6-oxo-4-trifluoromethyl-1,6-dihydropyrimidin-2-yl) amino (isobutyloxy) acetate; yellow viscous liquid; ¹ H-NMR ( CDCl ₃ , TMS, ppm): δ 0.82 (t, J = 7.1H
z, 3H), 0.87 (d, J = 6.7Hz, 3H), 0.90 (d, J = 6.7Hz, 3H),
1.86 (sep, J = 6.7Hz, 1H), 3.58 (s, 3H), 3.67-3.85
(m, 2H), 3.92 (d, J = 6.7Hz, 2H), 5.50 (s, 1H), 6.60 (s,
1H), 7.77 (s, 1H), 7.94 (s, 1H).

Example 188 (Compound No. 5-5) N- {2-bromo-3,5-bis (trifluoromethyl)
Methyl phenyl} -N- (1-ethyl-6-oxo-4-trifluoromethyl-1,6-dihydropyrimidin-2-yl) amino (hexyloxy) acetate; yellow viscous liquid; ¹ H-NMR ( CDCl ₃ , TMS, ppm): δ 0.79 to 0.91 (m.6H),
1.18 to 1.36 (m, 6H), 1.49 to 1.64 (m, 2H), 3.59 (s, 3
H), 3.68-3.85 (m, 2H), 4.04-4,21 (m, 2H), 5.50 (s,
1H), 6.61 (s, 1H), 7.75 (s, 1H), 7.94 (s, 1H).

Hereinafter, preparation examples and test examples of the agricultural and horticultural fungicides, herbicides, insecticides, and acaricides of the present invention are shown. The compound “No.” used in each test corresponds to the “compound number” in the compound list.

Formulation Example 1: Wetting agent 20 parts by weight of the compound of the present invention, Carplex 1180
(White carbon, Shionogi & Co., Ltd., trade name) 2
0 parts by weight, 52 parts by weight of ST kaolin clay (Kaolinite, Tsuchiya Kaolin Co., Ltd.), Solpol 9047K
(Anionic surfactant, Toho Chemical Co., Ltd., trade name)
5 parts by weight and 3 parts by weight of Lunox P65L (anionic surfactant, Toho Chemical Co., Ltd., trade name) were blended and uniformly mixed and pulverized to obtain a wettable powder containing 20% by weight of the active ingredient.

Formulation Example-2: Powder 2 parts by weight of the compound of the present invention, clay (manufactured by Nippon Talc) 9
3 parts by weight and 5 parts by weight of Carplex 1180 (White Carbon, Shionogi & Co., Ltd., trade name) were uniformly mixed and pulverized to produce a powder of 2% by weight of the active ingredient.

Formulation Example-3: Emulsion The compound of the present invention was dissolved in 20 parts by weight of a mixed solvent consisting of 35 parts by weight of xylene and 30 parts by weight of dimethylformamide, and dissolved in Solpol 3005X (a nonionic surfactant and an anion). 15 parts by weight of a mixture of water-soluble surfactants (trade name, Toho Chemical Co., Ltd.) was added to obtain an emulsion containing 20% by weight of the active ingredient.

Formulation Example-4: Flowable agent 30 parts by weight of the compound of the present invention, 5 parts by weight of Sorpol 9047K (same as above), and 3 parts by weight of Sorbon T-20 (nonionic surfactant, trade name of Toho Chemical Co., Ltd.) , 8 parts by weight of ethylene glycol and 44 parts by weight of water are wet-pulverized with a Dynomill (manufactured by Shinmaru Enterprises), and 1% by weight xanthan gum (natural polymer) is added to the slurry mixture.
An aqueous solution (10 parts by weight) was added and mixed and pulverized well to obtain a flowable agent containing 20% by weight of the active ingredient.

Test Example 1: Insecticidal effect on the larvae of the leafhopper, Leafhopper Leafhopper The seedlings of rice were set on a glass cylinder (inner diameter: 3 cm × length: 17 cm), and five third-stage larvae of the leafhopper, Leafhopper, were released. A water dilution (0.5 mL) of the insecticide (emulsion) of the present invention prepared according to the formulation of Formulation Example-3 was sprayed onto the above-mentioned glass cylinder using a spray tower (manufactured by Mizuho Rika) (1 concentration, 2 repetitions). ). Five days after the treatment, the larvae were examined for their life and death and agony, and the killing rate (%) was determined assuming that the agony worms were killed by 頭. The results are shown in Table 1.

[Table 1]

Test Example 2: Insecticidal effect on Japanese larva of Japanese moth Cabbage cut leaves (diameter 6 cm) were diluted with water for 1 minute in a water dilution of the insecticide (wettable powder) of the present invention prepared according to the formulation of Preparation Example 1. Dipped. After immersion, it was air-dried and placed in a plastic cup (inner diameter: 7 cm). Five third-instar larvae of the Japanese moth were released into this cup (1 concentration, 2 repetitions). After 4 days from the release, the larvae were examined for viability and agony, and the killing rate (%) was determined by assuming that the agony insects were 死 dead. Table 2 shows the results.

[Table 2]

Test Example-3: Acaricidal Effect on Adults of Dermatophagoid Spider Mites 10 adult female spider mites were released on cut leaves (3 cm in diameter) of kidney beans. A solution (3.5 mL) prepared by diluting the acaricide (wettable powder) of the present invention to a predetermined concentration with water, prepared according to the formulation of Formulation Example 1, was placed on the above cut leaves by a rotary spraying tower (manufactured by Mizuho Rika). ) (1 concentration, 2 replicates). Twenty-four hours after the treatment, the life and death of the adults were examined to determine the acaricidal rate (%). The results are shown in Table-3.

Test Example-4: Acaricidal effect on eggs of the spider mite Five adult female spider mites were released on the cut leaves (3 cm in diameter) of kidney beans. The eggs were laid on cut leaves for 20 hours after the release, and then the female adults were removed. A liquid (3.5 mL) obtained by diluting the acaricide (wettable powder) of the present invention prepared according to the formulation of Formulation Example 1 to a predetermined concentration with water was spread on the above disk by a rotary spraying tower (manufactured by Mizuho Rika). (1 concentration, 2 replicates). Eight days after the treatment, the number of unhatched eggs and the number of hatched larvae were examined to determine the ovality (%). The results are shown in Table-3.

[Table 3] Table-3. Acaricidal effect on mites and eggs of the spider mite ━━━━━━━━━━━━━━━━━━━━━━━━ Compound No. Concentration (ppm) Acaricidal rate (%) Egg killing Rate (%) ━━━━━━━━━━━━━━━━━━━━━━━━ 1- 4 500 100 100 1- 8 500 100 100 1-25 500 100 100 1-46 500 100 100 2-11 500 100 100 4-44 500 100 100 ━━━━━━━━━━━━━━━━━━━━━━━━

Test Example-5: Insecticidal effect on the larvae of Spodoptera litura (Lepidoptera: Noctuidae) In a water-diluted solution of the insecticide (wettable powder) of the present invention prepared according to the formulation of Preparation Example 1, 1 cut cabbage leaf (diameter 6 cm) was prepared. Soak for minutes. After immersion, air-dry and put in a plastic cup (7 cm inside diameter).
5 larvae were released (1 concentration, 2 repetitions). The larvae were kept in a constant temperature room at 25 ° C., and after 5 days from the release, the larvae were examined for viability and writhing, and the writhing larvae were killed by 頭 to determine the insecticidal rate (%). The results are shown in Table-4.

[Table 4] Table-4. Insecticidal effect of Spodoptera litura on larvae 化合物 Compound No. concentration (ppm) Insecticidal rate (%) ━━━━━━━━━━━━━━━ ━━ 1-34 500 100 1-36 500 100 2-24 500 100 2-26 500 100 2-43 500 100 3-12 500 100 3-15 500 100 4--4 500 100 4--8 500 100 4-36 500 100 ━━━━━━━━━━━━━━━━

Test Example-6: Insecticidal effect of adzuki beetle on adult adults Red bean beans 2 in a glass cylinder (inner diameter 3 cm x length 15 cm)
Individuals were put in and 10 adults of Azuki weevil were released. Insecticide of the present invention (emulsion) manufactured according to the formulation of Formulation Example-3
(0.3 mL) was sprayed onto the above-mentioned glass cylinder using a spray tower (manufactured by Mizuho Rika) (1 concentration, 2 repetitions). The larvae were kept in a constant temperature room at 25 ° C., and after 4 days from the treatment, the larvae were examined for viability and agony, and the killing rate (%) was determined by assuming that the agony worms were 死 dead. The results are shown in Table-5.

[Table 5] Table-5. Insecticidal effect of Azuki weevil on adult ━━━━━━━━━━━━━━━━━ Compound No. concentration (ppm) Insecticidal rate (%) ━━━━━━━━━━━━━━ ━━━ 1- 4 500 100 2-16 500 100 2-35 500 100 3-1 500 100 3-20 500 100 3-27 500 100 4-14 500 100 4-20 500 100 4-26 500 100 ━━ ━━━━━━━━━━━━━━━

Test Example-7: Pesticidal effect on larvae of peach peach aphids The petiole of radish leaves was inserted into a screw bottle (capacity: 10 mL) filled with water, and 5 to 6 peach peach aphids were inoculated per leaf. . After inoculation, glass cylinder (diameter: 3.5c
m, height: 15 cm, with a mesh lid), and aphids were grown in a thermostat at 25 ° C. for 3 days. After removing the aphid adults on the radish leaves, the leaves were formulated as Preparation Example-3
Was immersed (about 5 seconds) in a water dilution of the insecticide (emulsion) of the present invention produced according to the above-mentioned formula, and returned into a glass cylinder (one concentration, two repetitions). It was kept in a constant temperature room at 25 ° C., and on the fourth day after the treatment, the number of aphids on radish leaves was examined, and the insecticidal rate (%) was determined based on the results. The results are shown in Table-6.

[Table 6] Table-6. Insecticidal effect of peach aphid on larvae ━━━━━━━━━━━━━━━━ Compound No. concentration (ppm) Insecticidal rate (%) ━━━━━━━━━━━━━━ ━━ 1-14 500 100 1-32 500 100 1-44 500 100 2-18 500 100 2-20 500 100 2-29 500 100 3-5 500 100 ━━━━━━━━━━━━━ ━━━

[0294]

The pesticidal composition comprising the 2-anilino-4 (3H) -pyrimidinone derivative of the present invention as an active ingredient is:
In particular, it has an extremely excellent control effect on harmful plant pathogens, insects, mites and weeds in agricultural and horticultural applications, and is useful as an agricultural and horticultural agricultural chemical.

 ──────────────────────────────────────────────────続 き Continuing on the front page (72) Inventor Natsuko Okano 2-19-15, Chuo-Rinkan, Yamato-shi, Kanagawa (72) Maho Nagaoka 2-16-6, Ohno Sagamihara, Sagamihara-shi, Kanagawa (72) Inventor Kenichi Sato 35-11 Kamimizo, Sagamihara City, Kanagawa Prefecture (72) Inventor Chikako Ota 1000 Kamoshitacho, Aoba-ku, Yokohama-shi, Kanagawa Prefecture Mitsubishi Chemical Corporation Yokohama Research Laboratory (72) Inventor Toshiki Fukuchi 1000 Kamoshita-cho, Aoba-ku, Yokohama-shi, Kanagawa Prefecture Mitsubishi Chemical Corporation Yokohama Research Laboratory (72) Inventor Risa Yamada 1000 Kamoshitacho, Aoba-ku, Yokohama-shi, Kanagawa Prefecture Mitsubishi Chemical Research Laboratory Yokohama Research Laboratory F-term (reference) 4C086 AA01 BC42 MA01 MA04 MA52 MA63 NA14 ZC61 4H011 AC01 AC04 BA01 BB09 BC03 BC18 BC19 BC20 DA02 DA14 DA15 DA16 DD03 DD04 DH03

Claims (7)

[Claims] 1. A compound of the general formula (1) Wherein R ¹ is a halogen atom, a C ₁ -C ₄ alkyl group, C ₁
-C ₄ haloalkyl group, or an optionally substituted phenyl group, R ² represents a hydrogen atom or a halogen atom.
R ³ is a C ₁ -C ₆ alkyl group, a C ₁ -C ₆ haloalkyl group,
(C ₁ -C ₆ alkoxy) C ₁ -C ₆ alkyl group, C ₃ -C ₆
Alkenyl group, C ₃ -C ₆ haloalkenyl group, C ₃ -C ₆ alkynyl group, C ₃ -C ₆ haloalkynyl group, C ₃ -C ₈ cycloalkyl group, are also aralkyl group or a substituted substituted Represents a C _{2 to} C ₆ vinyl group which may be substituted. R ⁴ is represented by the following general formula (2): (Wherein, R ⁵ and R ⁶ each independently represent a C ₁ -C ₆ alkyl group or a C ₃ -C ₈ cycloalkyl group, and n is 0-5
Represents an integer. ) Represents a substituent. X is a hydrogen atom, a halogen atom, C ₁ -C ₄ alkyl group, C ₁ -C ₄ haloalkyl groups, C ₃ -C ₆ alkenyl group, C ₃ -C ₆ alkynyl group, C ₁ -C ₅ acyl group, a carboxy group , (C ₁ -C ₄ alkoxy) carbonyl, cyano, hydroxy, C
C ₁ -C ₄ alkoxy group, C ₁ -C ₄ haloalkoxy group, (C
₁ -C ₄ alkoxy) C ₁ -C ₄ alkoxy, carboxy (C ₁ -C ₄ alkoxy) group, (C ₁ -C ₄ alkoxy) carbonyl (C ₁ -C ₄ alkoxy) group, C ₃ -C ₆ alkenyl oxy group, C ₃ -C ₆ alkynyloxy group, an optionally substituted phenyl group, C ₁ -C ₅ acyloxy group, a mercapto group, C ₁ -C ₄ alkylthio group, C ₁ -C ₄
Haloalkylthio groups, C ₁ -C ₄ alkylsulfinyl group, C ₁ -C ₄ haloalkylsulfinyl group, C ₁ -C ₄ alkylsulfonyl group, C ₁ -C ₄ haloalkylsulfonyl group, an amino group, C ₁ -C ₄ alkylamino Group, di (C _1-
C ₄ alkyl) amino group, C ₁ -C ₅ acylamino group, C ₁
-C ₄ alkyl sulfonylamino group or a nitro group, m represents an integer from 1 to 5. Where m is 2 to 5
X may be the same or different. A 2-anilino-4 (3H) -pyrimidinone derivative represented by｝. 2. A compound of the general formula (3) (Wherein, R ¹ , R ² , R ³ , X and m represent the same meaning as described above), and a general formula (4) (Wherein, R ⁴ has the same meaning as described above, and L represents a leaving group). The reaction is carried out in the presence of a base. ] (Wherein, R ¹ , R ² , R ³ , R ⁴ , X and m have the same meanings as described above.) A method for producing a 2-anilino-4 (3H) -pyrimidinone derivative represented by the formula: 3. The 2-anilino-4 (3) according to claim 1,
H) -Pest control agents containing a pyrimidinone derivative as an active ingredient. 4. The 2-anilino-4 (3) according to claim 1,
H) -Agrochemicals containing a pyrimidinone derivative as an active ingredient. 5. The 2-anilino-4 (3) according to claim 1,
H) -Insecticides and miticides containing a pyrimidinone derivative as an active ingredient. 6. The 2-anilino-4 (3) according to claim 1,
H) -A fungicide containing a pyrimidinone derivative as an active ingredient. 7. The 2-anilino-4 (3) according to claim 1,
H) -A herbicide containing a pyrimidinone derivative as an active ingredient.