JP3122811B2 - Substituted aminoquinazolinone (thione) derivatives or salts thereof, intermediates and pesticides, and methods of using the same - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

The present invention relates to a novel substituted aminoquinazolinone (thione) derivative, a pesticidal agent containing the derivative as an active ingredient, and a method for using the same.

[0002]

2. Description of the Related Art JP-A-1-132580 and JP-A-2-29
JP-A-0871 and JP-A-6-234748 disclose that a triazinone derivative or an imidazole derivative is useful as a pesticidal agent.

[0003]

DISCLOSURE OF THE INVENTION The present inventors have conducted intensive studies to create a novel pesticidal agent, and as a result, completed the present invention, and represented by the general formula (I) of the present invention. The substituted aminoquinazolinone (thione) derivative represented by the general formula (II), which is an intermediate compound for producing the substituted aminoquinazolinone (thione) derivative, is a novel compound which has not been described in the literature. The substituted aminoquinazolinone (thione) derivative represented by the formula or a salt thereof has an excellent insecticidal effect on various pests at a low dose.

[0004]

The present invention provides a compound represented by the general formula (I):

Embedded image Wherein R is a hydrogen atom, a hydroxyl group, a formyl group, (C _1-12 )
Alkyl group, halo (C _1-6 ) alkyl group, hydroxy (C _1-6 )
Alkyl group, (C _2-6 ) alkenyl group, (C _2-6 ) alkynyl group, (C _1-6 ) alkoxy group, halo (C _1-6 ) alkoxy group, (C
_1-6 ) alkoxy (C _1-3 ) alkyl group, (C _1-6 ) alkoxy (C
_1-3 ) alkoxy (C _1-3 ) alkyl group, (C _1-6 ) alkylthio group, halo (C _1-6 ) alkylthio group, (C _1-6 ) alkylsulfinyl group, (C _1-6 ) alkyl Sulfonyl group, (C _1-6 ) alkylthio (C _1-3 ) alkyl group,

A di (C _1-6 ) alkoxy (C _1-3 ) alkyl group and an amino (C _1-6 ) alkyl group, which may be the same or different, may be the same or different, and may be a (C _1-6 ) alkyl Group, halo (C _1-6 ) alkyl group, (C _2-6 ) alkenyl group, or (C _2-6 ) amino group having 1 to 2 substituents selected from alkynyl group (C _1-6 )
Alkyl group, cyano (C _1-6 ) alkyl group, (C _1-6 ) alkylcarbonyl group, (C _1-6 ) alkoxycarbonyl group, hydroxycarbonyl (C _1-3 ) alkyl group, (C _1-6 ) Alkoxycarbonyl (C _1-3 ) alkyl group, aminocarbonyl group, may be the same or different, (C _1-6 ) alkyl group, (C _2-6 ) alkenyl group, or (C _2-6 ) alkynyl group Selected 1-2
Amino carbonyl group having one substituent, (C _3-6 ) cycloalkyl (C _1-3 ) alkyl group, phenyl (C _1-3 ) alkyl group, which may be the same or different, a halogen atom, a nitro group, Cyano group, (C _1-6 ) alkyl group, halo (C _1-6 ) alkyl group, (C _1-6 ) alkoxy group, halo (C _1-6 ) alkoxy group, (C
_1-6 ) phenyl having 1 to 5 substituents on a ring selected from an alkylthio group or a halo (C _1-6 ) alkylthio group
(C _1-3 ) alkyl group, phenylcarbonyl group,

[0006] A halogen atom,
Nitro group, cyano group, (C _1-6 ) alkyl group, halo (C _1-6 ) alkyl group, (C _1-6 ) alkoxy group, halo (C _1-6 ) alkoxy group, (C _1-6 ) A phenylcarbonyl group having 1 to 5 substituents on the ring selected from an alkylthio group or a halo (C _1-6 ) alkylthio group, a phenylthio group, which may be the same or different, a halogen atom, a nitro group, a cyano group; Group, (C _1-6 )
Alkyl group, halo (C _1-6) alkyl, (C _1-6) alkoxy groups, halo (C _1-6) alkoxy groups, (C _1-6) alkylthio group,
Or a phenylthio group having 1 to 5 substituents on the ring selected from a halo (C _1-6 ) alkylthio group, a phenylsulfonyl group, which may be the same or different, a halogen atom, a nitro group, a cyano group, ( C _1-6) alkyl groups, halo (C _1-6) alkyl, (C _1-6) alkoxy groups, halo (C _1-6) alkoxy groups, (C _1-6) alkylthio group, or halo (C _1-6 ) a phenylsulfonyl group having 1 to 5 substituents selected from an alkylthio group on the ring, a phenyl (C _1-6 ) alkylsulfonyl group, which may be the same or different, a halogen atom, a nitro group, Cyano group, (C _1-6 ) alkyl group, halo (C _1-6 ) alkyl group, (C _1-6 ) alkoxy group, halo (C _1-6 ) alkoxy group, (C
_1-6 ) phenyl having 1 to 5 substituents on a ring selected from an alkylthio group or a halo (C _1-6 ) alkylthio group
(C _1-6 ) alkylsulfonyl group, phenyloxycarbonyl group, which may be the same or different, a halogen atom, a nitro group, a cyano group, a (C _1-6 ) alkyl group, a halo (C _1-6 ) alkyl group, (C _1-6 ) alkoxy group, halo (C _1-6 ) alkoxy group, (C
_1-6) alkylthio group, or a halo (C _1-6) phenyloxycarbonyl group having from 1 to 5 substituents on the ring selected from alkylthio, phenyloxy (C _1-3) alkyl group,

A halogen atom,
Nitro group, cyano group, (C _1-6 ) alkyl group, halo (C _1-6 ) alkyl group, (C _1-6 ) alkoxy group, halo (C _1-6 ) alkoxy group, (C _1-6 ) An alkylthio group, or a phenyloxy (C _1-3 ) alkyl group having 1 to 5 substituents on a ring selected from a halo (C _1-6 ) alkylthio group, a phenyl (C _2-6 ) alkenyl group, The same or different, a halogen atom, a nitro group, a cyano group, a (C _1-6 ) alkyl group, a halo (C _1-6 ) alkyl group, a (C _1-6 ) alkoxy group, a halo (C _1-6 ) Alkoxy group,
A phenyl (C ₂₎ having 1 to 5 substituents on a ring selected from a (C _1-6 ) alkylthio group, a halo (C _1-6 ) alkylthio group, and a (C _1-2 ) alkylenedioxy group _-6 ) alkenyl group,
A phenyl (C _2-6 ) alkynyl group, which may be the same or different, a halogen atom, a nitro group, a cyano group, a (C _1-6 ) alkyl group, a halo (C _1-6 ) alkyl group, a (C _1-6 ) Alkoxy group, halo (C _1-6 ) alkoxy group, (C _1-6 ) alkylthio group, halo (C
_1-6 ) an alkylthio group, or a phenyl ( _C2-4 ) alkynyl ( _C1-3 ) alkyl group having 1 to 5 substituents on the ring selected from ( _C1-2 ) alkylenedioxy groups A 1,3-dioxolan-2-yl (C _1-3 ) alkyl group or a phthalimide (C _1-6 ) alkyl group.

R ¹ may be the same or different and include an oxygen atom,
A 5- to 6-membered heterocyclic group having 1 to 3 heteroatoms selected from a sulfur atom or a nitrogen atom, which may be the same or different, a halogen atom, a cyano group, (C
_1-6 ) an alkyl group, a halo (C _1-6 ) alkyl group, or a (C _1-6 ) alkoxy group, which may have 1 to 5 substituents, and a nitrogen atom in the heterocyclic group. May also represent an N-oxide group. Y represents an oxygen atom or a sulfur atom;
Is

Embedded image ^{-N = C (R 2) -} ( wherein, R ² is a hydrogen atom, (C _1-6) alkyl group, or halo (C
_1-6 ) represents an alkyl group. ),

[0009]

Wherein R ² is the same as above, and R ³ is a hydrogen atom, a (C _1-6 ) alkyl group, a formyl group, a (C ₁ ) -N (R ³ ) -CH (R ² )- _-3 ) an alkylcarbonyl group,
A halo (C _1-3 ) alkylcarbonyl group and a (C _1-3 ) alkyldithiocarbonyl group. ) Or

Embedded image -N (R ³⁾ -CO- (wherein, R ³ is the same. Above) indicates, X is the same or different, a halogen atom, a hydroxyl group, a nitro group, a cyano group, (C _1-6 ) alkyl group, halo (C _1-6 ) alkyl group, (C _1-6 )
Alkoxy group, halo ( _C1-6 ) alkoxy group, ( _C1-3 ) alkylenedioxy group, hydroxycarbonyl group, ( _C1-6 ) alkoxycarbonyl group, ( _C2-6 ) alkenyloxycarbonyl group, ( C _2-6) alkynyloxy carbonyl group selection, aminocarbonyl group, which may be identical or different, (C _1-6) alkyl, (C _2-6) alkenyl group, or (from C _2-6) alkynyl group Or an aminocarbonyl group having 1 to 2 substituents, an amino group, or the same or different, (C
_1-6 ) an alkyl group, a ( _C2-6 ) alkenyl group, or an amino group having 1 to 2 substituents selected from a ( _C2-6 ) alkynyl group, and n is an integer of 0 to 4 Is shown. A substituted aminoquinazolinone (thione) derivative or a salt thereof,
General formula (II) which is the intermediate

[0010]

Embedded image [Wherein, X may be the same or different, and a halogen atom,
Hydroxyl group, nitro group, cyano group, (C _1-6 ) alkyl group, halo
(C _1-6 ) alkyl group, (C _1-6 ) alkoxy group, halo (C _1-6 ) alkoxy group, (C _1-3 ) alkylenedioxy group, hydroxycarbonyl group, (C _1-6 ) alkoxy Carbonyl group, (C _2-6 )
Alkenyloxycarbonyl group, (C _2-6 ) alkynyloxycarbonyl group, aminocarbonyl group, which may be the same or different, (C _1-6 ) alkyl group, (C _2-6 ) alkenyl group, or (C _{2- 6} ) an aminocarbonyl group having 1 to 2 substituents selected from an alkynyl group, an amino group, or the same or different, a (C _1-6 ) alkyl group, a (C _2-6 ) alkenyl group, Or 1-2 selected from (C _2-6 ) alkynyl groups
Represents an amino group having three substituents, n represents an integer of 0 to 4, and Y represents an oxygen atom or a sulfur atom. And a substituted aminoquinazolinone (thione) derivative as an active ingredient and a method for using the same.

[0011]

BEST MODE FOR CARRYING OUT THE INVENTION The substituted aminoquinazolinone (thione) derivative represented by the general formula (I) of the present invention, in the definition of each substituent, "halogen atom" means chlorine atom, bromine atom, iodine atom or fluorine atom. It represents an atomic, "(C ₁ - ₁₂₎ alkyl group"
Represents a linear or branched alkyl group having 1 to 12 carbon atoms, for example, methyl, ethyl, n-propyl,
i-propyl, n-butyl, i-butyl, s-butyl,
An alkyl group such as t-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, etc.
₁ - ₆₎ may be the same or different from the alkyl group "refers to one or more linear or branched alkyl group having a carbon number of 1 to 6 substituted with a halogen atom," (C ₂ - ₆₎ a straight or branched alkenyl group having 2 to 6 carbon atoms having one or more double bonds and alkenyl group "," halo (C ₂ - ₆₎
It may be the same or different from the alkenyl group "refers to one or more straight or branched alkenyl group having a carbon number of 2 to 6 substituted with a halogen atom," (C ₂ - ₆₎ alkynyl the "a straight or branched alkynyl group having 2 to 6 carbon atoms having one or more triple bonds," halo (C ₂ - ₆₎
"Alkynyl group" may be the same or different, and represents a straight-chain or branched alkynyl group having 2 to 6 carbon atoms substituted with one or more halogen atoms. 5 to 6-membered heterocycle having one or more heteroatoms selected from an atom, a sulfur atom or a nitrogen atom or a nitrogen atom "is, for example, furan, thiophene, pyrrole, oxazole, thiazole, pyrazole, imidazole,
1,2,3-thia Zia tetrazole, 1,2,4-thia diazo <br/> Lumpur, 1,2,5 thia Zia tetrazole, 1,3,4-thia
Shown Zia tetrazole, 1,2,4-triazole, pyridine, pyridazine, pyrimidine, pyrazine, pyrrolidine, piperidine, morpholine, thiomorpholine, dithiolane, dithiane, piperazine, dioxirane, a 5-6 membered heterocyclic ring such as imidazolidine or tetrahydrofuran Shall be.

[0012] Preferred substituents in substituted aminoquinazolinone (thione) derivative represented by the general formula (I), R is a formyl group, (C ₁ - ₆₎ alkyl, (C ₂ - ₆₎ alkenyl group,
(C ₂ - ₆₎ alkynyl, (C ₁ - ₆₎ alkylcarbonyl groups, (C
₁ - ₆₎ alkoxycarbonyl group, (C ₁ - ₆₎ alkylthio group,
Halo (C ₁ - ₆₎ alkylthio group, a phenyl group, a phenyl group having a substituent, phenyl having a substituent (C ₁ - ₆₎ alkyl group, a phenyl having a substituent (C ₂ -
₆₎ phenyl (C ₂ having an alkenyl group, or a substituent - ₆₎ alkynyl group, R ¹ is pyridyl group, especially 3-pyridyl group, Y is an oxygen atom or a sulfur atom, Z is

Embedded image ^{-N (R 3) -CH (R} 2) - a and, R ³ and R ² is a hydrogen atom or - (C _{1 6)} alkyl group, X is a halogen atom, (C ₁ - ₆ ) An alkyl group or a methylenedioxy group, and n is preferably from 0 to 2. Examples of the salt of the substituted aminoquinazolinone (thione) derivative represented by the general formula (I) include salts of alkali metal atoms such as sodium and potassium in addition to mineral salts such as hydrochloric acid, sulfuric acid and nitric acid. be able to.

The compound of the formula (II), which is an intermediate of the present invention, can be produced by the following production method. Manufacturing method 1.

Embedded image (In the formula, X and n are as defined above, R ⁴ represents a (C _1-6 ) alkyl group, and Hal represents a halogen atom.)

The compound represented by the general formula (II-1) can be produced by reacting the compound represented by the general formula (III) with hydrazine hydrate in the presence of an inert solvent. The inert solvent that can be used in this reaction may be any solvent that does not significantly inhibit the progress of this reaction, and examples thereof include alcohols such as methanol, ethanol, propanol, and butanol, and halogenated hydrocarbons such as dichloromethane, chloroform, and carbon tetrachloride. , Aromatic hydrocarbons such as benzene, toluene and xylene, nitriles such as acetonitrile and benzonitrile, cellsolves such as methylcellosolve, ethers such as diethyl ether, diglyme, dioxane and tetrahydrofuran, dimethylformamide, dimethylacetamide And amides such as 1,3-dimethyl-2-imidazolidinone and 1-methyl-2-pyrrolidone, and inert solvents such as dimethyl sulfoxide, sulfolane, and water. These inert solvents can be used alone. Or mix two or more To be able to use.

The reaction may be carried out at a temperature in the range of room temperature to the boiling point of the inert solvent used, preferably from room temperature to 90 ° C.
Range. Since this reaction is an equimolar reaction, the general formula (I
The compound represented by II) and the hydrazine hydrate may be used in equimolar amounts, but any of the reactants may be used in excess, and it is preferable to use the hydrazine hydrate in excess. The reaction time is not fixed depending on the reaction scale, the reaction temperature and the like, but is in the range of several minutes to 48 hours. After completion of the reaction, the target substance can be produced by treating the reaction system containing the target substance by a conventional method and, if necessary, purifying it by recrystallization, dry column chromatography or the like. The compound represented by the general formula (III) is a compound represented by Collect. Czech. Chem. Co.
mmn. (Vol. 55), 752 (1990).

Manufacturing method 2.

Embedded image (In the formula, R ⁴ , X, n and Y are the same as described above.)

2-1. General formula (VIII) → General formula (VI) By reacting a compound represented by general formula (VIII) with a compound represented by general formula (VII) in the presence of an inert solvent and a catalyst, The compound represented by (VI) can be produced. As the inert solvent that can be used in this reaction, for example, the inert solvents exemplified in Production Method 1 can be used, and these inert solvents can be used alone or in combination of two or more. As the catalyst, for example, hydrochloric acid,
In addition to inorganic acids such as sulfuric acid, acetic acid, paratoluenesulfonic acid and the like can be used, and the amount of use is in the range of 0.001% by weight to 10% by weight based on the compound represented by the general formula (VIII). May be present in the reaction system.

Since this reaction is an equimolar reaction, the general formula (VII)
The compound represented by I) and the compound represented by formula (VII) may be used in equimolar amounts, but any one of the reactants may be used in excess. The reaction may be carried out at any temperature within the range from room temperature to the boiling point of the inert solvent used, and preferably from room temperature to 90 ° C. The reaction time is not fixed depending on the reaction scale, the reaction temperature and the like, but is in the range of several minutes to 48 hours. After completion of the reaction, the target substance can be produced from the reaction system containing the target substance in the same manner as in Production Method 1.
The compound represented by the general formula (VIII) may be a commercially available compound, and can also be produced by nitrating a substituted benzaldehyde.

2-2. General formula (VI) → general formula (V) By reacting the compound represented by the general formula (VI) with a reducing agent in the presence or absence of an inert solvent, or by catalytic reduction, the general formula ( The compound represented by V) can be produced. As the reducing agent in the present reduction reaction, for example, NaBH
₃ CN, metal hydrides such as LiBH ₃ CN, can be used reducing agents such as BH _3, to the number of moles of hydride reducing agent to the compound represented by the amount used of the general formula (VI) What is necessary is just to select and use suitably from the range of equimolar to excess molar in terms of conversion. The inert solvent that can be used in this reaction may be any solvent that does not significantly inhibit the progress of this reaction.Examples include alcohols such as methanol, ethanol, propanol and butanol, cellsolves such as methylcellsolve, diethyl ether, diglyme, and the like. Ethers such as dioxane and tetrahydrofuran, esters such as ethyl acetate, dimethylformamide, dimethylacetamide, 1,3-
Examples include amides such as dimethyl-2-imidazolidinone and 1-methyl-2-pyrrolidone, and inert solvents such as dimethyl sulfoxide, sulfolane, and water. These inert solvents may be used alone or in combination of two or more. Can be used in combination.

The reaction is carried out under acidic to neutral conditions at pH 1 to 7
, Preferably in the range of pH 4 to 6, and the pH may be adjusted by adding hydrogen chloride, hydrogen bromide, or the like to the reaction system. The reaction temperature is selected from the range of 0 ° C. to the boiling point of the solvent, and is preferably in the range of room temperature to 70 ° C. The reaction time is not fixed depending on the reaction scale, the reaction temperature and the like, but is in the range of several minutes to 48 hours. After completion of the reaction, the target substance can be produced from the reaction system containing the target substance in the same manner as in Production Method 1. Next, when performing catalytic reduction as a reduction reaction, for example, "New experimental chemistry course"
(Vol. 15-II: Maruzen) and the like. Examples of usable inert solvents include alcohols such as methanol, ethanol, propanol and butanol, cellsolves such as methylcellsolve, diethyl ether, and the like. Diglyme, dioxane, ethers such as tetrahydrofuran, hexane, hydrocarbons such as cyclohexane, acetic acid, fatty acids such as ethyl acetate or esters thereof, dimethylformamide, dimethylacetamide,
Examples thereof include amides such as 1,3-dimethyl-2-imidazolidinone and 1-methyl-2-pyrrolidone, and ureas such as tetramethylurea. These inert solvents may be used alone or in combination of two or more. Can be used in combination.

Examples of the catalyst used in the present reduction reaction include, for example, typical catalytic reduction catalysts such as palladium carbon, palladium black, platinum dioxide, Raney nickel and the like. The amount may be selected from the range of 0.1% molar equivalent to 5% molar equivalent to the compound to be used, and is preferably in the range of 0.5% molar equivalent to 1% molar equivalent. The hydrogen pressure in this reaction is from normal pressure to
It is in the range of 300 atm, preferably in the range of normal pressure to 50 atm. The reaction may be carried out at any temperature within the range of room temperature to the boiling point of the inert solvent used, preferably from room temperature to 70 ° C.
Range. The reaction time is not fixed depending on the reaction scale, the reaction temperature and the like, but is in the range of several minutes to 48 hours. After completion of the reaction, the target substance can be produced from the reaction system containing the target substance in the same manner as in the case where the reducing agent is used.

2-3. General formula (V) → General formula (IV) A compound represented by the general formula (V) and 1,1′-carbonylbis-1H-imidazole (CDI), alkoxycarbonyl halide, phosgene or The compound represented by the general formula (IV) can be produced by reacting thiophosgene with an inert solvent in the presence or absence of a base. Examples of the inert solvent that can be used in this reaction include ethers such as diethyl ether, diglyme, dioxane, and tetrahydrofuran; aromatic hydrocarbons such as benzene, toluene, and xylene; and water. The active solvents can be used alone or in combination of two or more. As the base, an inorganic base or an organic base can be used, for example, sodium hydroxide,
Potassium hydroxide, magnesium hydroxide, sodium carbonate, sodium hydrogen carbonate, potassium carbonate and other alkali metal or alkaline earth metal hydroxides, carbonates and other inorganic bases, triethylamine, pyridine and the like can be exemplified. When CDI is used as an agent, the reaction can be carried out in the absence of a base.

The base may be used in an amount of at least twice the amount of the compound represented by the general formula (V). The reaction may be carried out at any temperature within the range from room temperature to the boiling point of the inert solvent used, and preferably from room temperature to 100 ° C. The reaction time is not fixed depending on the reaction scale, the reaction temperature and the like, but is in the range of several minutes to 48 hours. After completion of the reaction, the target substance can be produced from the reaction system containing the target substance in the same manner as in Production Method 1.

2-4. General formula (IV) → General formula (II) The compound represented by the general formula (IV) is subjected to an alkali hydrolysis reaction in the presence of an inert solvent to give a compound of the general formula (II). The compounds represented can be prepared. Examples of the inert solvent that can be used in this reaction include alcohols such as methanol, ethanol, propanol and butanol, aromatic hydrocarbons such as benzene, toluene and xylene, ethers such as diethyl ether, diglyme, dioxane and tetrahydrofuran. And inert solvents such as water and the like. These inert solvents can be used alone or in combination of two or more.

As the base, hydroxides of alkali metals or alkaline earth metals such as sodium hydroxide, potassium hydroxide and magnesium hydroxide can be used. or,
Depending on the alkyl group of R ^4, the reaction can be performed under acidic conditions using an organic acid such as trifluoroacetic acid or hydrochloric acid, or an inorganic acid. The reaction temperature may be appropriately set in the range of 0 ° C. to the boiling point of the inert solvent used. The reaction time depends on the reaction scale,
It is not constant depending on the reaction temperature and the like, but is in the range of several minutes to 48 hours. After completion of the reaction, the target substance can be produced from the reaction system containing the target substance in the same manner as in Production Method 1.

In the following, typical examples of the compounds represented by the general formula (II) produced by Production Methods 1 and 2 are shown in Table 1, but the present invention is not limited to these. General formula (II)

Embedded image

[0027]

[Table 1]

[0028]

[Table 2]

[0029]

[Table 3]

[0030]

[Table 4]

[0031]

[Table 5]

[0032]

[Table 6]

Next, a typical method for producing the aminoquinazolinone (thione) derivative represented by the general formula (I) of the present invention or a salt thereof is schematically shown below. Manufacturing method 3.

Embedded image (In the formula, R ¹ , R ¹ , R ² , R ³ , X, n, Y and Hal are the same as above, provided that R and R ³ exclude a hydrogen atom.)

3-1. General formula (II) → General formula (I-1) A compound represented by the general formula (II) is reacted with a compound represented by the general formula (X) in the presence of an inert solvent and a catalyst to form a compound. An aminoquinazolinone (thione) derivative represented by the formula (I-1) can be produced. The target compound can be produced by carrying out this reaction in the same manner as in Production Method 2-1.

3-2. Formula (I-1) → Formula (I-3) Aminoquinazolinone (thione) represented by Formula (I-1)
The aminoquinazolinone (thione) derivative represented by the general formula (I-3) is produced by reacting the derivative with the compound represented by the general formula (IX) in the presence or absence of an inert solvent and a base. can do. As the inert solvent that can be used in this reaction, for example, the inert solvent exemplified in Production Method 1 can be used. As the base, an inorganic base or an organic base can be used. For example, CH ₃ ONa, C ₂ H ₅ ONa, tC _{4
H 9 ONa, CH 3 OK,} C 2 H 5 OK, alcoholates such as tC ₄ H ₉ OK, alkali metal hydrides such as NaH may also be used, the amount used by the general formula (I-1) The reaction may be carried out by appropriately selecting an equimolar to excess molar amount relative to the aminoquinazolinone (thione) derivative represented.

The reaction may be carried out at a temperature ranging from 0 ° C. to the boiling point of the inert solvent used, preferably from room temperature to 70 ° C. The reaction time is not constant depending on the reaction scale, the reaction temperature and the like, but may be in the range of several minutes to 48 hours. After completion of the reaction, the target substance can be produced from the reaction system containing the target substance in the same manner as in Production Method 1.

3-3. Formula (I-3) → Formula (I-5) Aminoquinazolinone (Thion) represented by Formula (I-3)
The derivative is reacted with a reducing agent in the presence or absence of an inert solvent, or is subjected to catalytic reduction to obtain a compound of the general formula (I-5)
The aminoquinazolinone (thione) derivative represented by the following formula can be produced. The reaction can be carried out in the same manner as in Production Method 2-2 to produce the desired product. 3-4. General formula (I-1) → General formula (I-2) The reaction can be carried out in the same manner as in 3-3 to produce the desired product. 3-5. General formula (I-2) → General formula (I-4) The target compound can be produced by carrying out the reaction in the same manner as in 3-2. 3-6. Formula (I-4) → Formula (I-5) Aminoquinazolinone (Thion) represented by Formula (I-4)
The aminoquinazolinone (thione) derivative represented by the general formula (I-5) is produced by reacting the derivative with the compound represented by the general formula (XI) in the presence or absence of an inert solvent and a base. can do.

Manufacturing method 4.

Embedded image (In the formula, R ¹ , R ¹ , R ³ , X, Y, n and Hal are the same as above, provided that R excludes a hydrogen atom.)

4-1. General formula (VIII) → general formula (XIII) By reacting a compound represented by general formula (VIII) with a compound represented by general formula (XII) in the presence of an inert solvent and a catalyst, The compound represented by (XIII) can be produced. The target compound can be produced by carrying out this reaction in the same manner as in Production Method 2-1. 4-2. General formula (XIII) → General formula (XIV) A compound represented by the general formula (XIII) is reacted with a reducing agent in the presence or absence of an inert solvent, or is subjected to catalytic reduction to form a compound of the general formula (XIV) ) Can be produced. The reaction can be carried out in the same manner as in Production Method 2-2 to produce the desired product. 4-3. General formula (XIV) → General formula (XV) A compound represented by the general formula (XIV) is reacted with a reducing agent in the presence or absence of an inert solvent, or is subjected to catalytic reduction to form a compound of the general formula (XV ) Can be produced. The reaction can be carried out in the same manner as in Production Method 2-2 to produce the desired product.

4-4. General formula (XV) → General formula (I-5) Inactive compound represented by general formula (XV) with 1,1′-carbonylbis-1H-imidazole (CDI), alkoxycarbonyl halide, phosgene or thiophosgene The aminoquinazolinone (thione) derivative represented by the general formula (I-6) can be produced by reacting in the presence of a solvent in the presence or absence of a base. The reaction can be carried out in the same manner as in Production Method 2-3 to produce the desired product. 4-5. Formula (I-6) → Formula (I-7) Aminoquinazolinone (Thion) represented by Formula (I-6)
The aminoquinazolinone (thione) derivative represented by the general formula (I-7) is produced by reacting the derivative with the compound represented by the general formula (IX) in the presence or absence of an inert solvent and a base. can do. This reaction is carried out according to Production method 3-2.
In the same manner as in the above, the target product can be manufactured.

The typical examples of the aminoquinazolinone (thione) derivative represented by the general formula (I) of the present invention or salts thereof are shown in Table 2 below, but the present invention is not limited thereto. In addition, the symbol in Table 2, Table 4, and Table 6 shows the following substituent. Ph: phenyl group Q _1: 2-pyridyl group Q _2: 3- pyridyl group Q _3: 4-pyridyl group Q _4: 2-pyridyl -N- oxide groups Q _5: 3- pyridyl -N- oxide groups Q _6: 4-pyridyl-N-oxide group Q ₇ : thiazol-5-yl group Q ₈ : furan-2-yl group Q ₉ : 1,3-dioxolan-2-yl group Q ₁₀ : phthalimido-1-yl group General formula (I ')

Embedded image

[0042]

[Table 7]

[0043]

[Table 8]

[0044]

[Table 9]

[0045]

[Table 10]

[0046]

[Table 11]

[0047]

[Table 12]

[0048]

[Table 13]

[0049]

[Table 14]

[0050]

[Table 15]

[0051]

[Table 16]

[0052]

[Table 17]

[0053]

[Table 18]

[0054]

[Table 19]

[0055]

[Table 20]

[0056]

[Table 21]

[0057]

[Table 22]

[0058]

[Table 23]

[0059]

[Table 24]

[0060]

[Table 25]

In Table 2, compound numbers 283, 293, 3
Table 3 shows the NMR data of the compounds of 68, 369, 371, 375, 382 and 383.

[Table 26]

[0062]

[Table 27]

Formula (I '')

Embedded image

[0064]

[Table 28]

[0065]

[Table 29]

[0066]

[Table 30]

[0067]

[Table 31]

[0068]

[Table 32]

[0069]

[Table 33]

In Table 4, compound numbers 411, 473, 4
75, 476, 477, 480, 481, 482, 48
6,487,488,490,491,491.1,4
The NMR data of the compounds 91.2 and 491.3
It is shown in the table.

[0071]

[Table 34]

[0072]

[Table 35]

Formula (I '' ')

Embedded image

[0074]

[Table 36]

[0075]

[Table 37]

[0076]

[Table 38]

[0077]

[Table 39]

[0078]

[Table 40]

[0079]

The present invention will be described in more detail with reference to the following Examples, which by no means limit the present invention. Embodiment 1 FIG. 3-amino-3,4-dihydro-2 (1
Production of H) -quinazolinone (Compound No. II-1).

Embedded image 2.44 g (0.01 mol) of methyl 2-bromomethylphenylcarbamate was dissolved in 20 ml of methanol, 5 g (0.1 mol) of hydrazine hydrate was added to the solution, and the reaction was carried out under reflux for 3 hours. Was. After completion of the reaction, excess hydrazine hydrate and the solvent are distilled off from the reaction solution containing the target product under reduced pressure to obtain a crude product, and the obtained crude product is recrystallized from 95% methanol to obtain a crude product. 1.55 g of the product were obtained. Physical properties: m. p. 178.4-183.5 ° C Yield: 9
5%

Embodiment 2 FIG. 2-1. Methyl 2- (4,5-methylenedioxy-
Production of 2-nitrophenylmethylidene) carbazic acid.

Embedded image 3.9 g (0.02 mol) of 6-nitropiperonal, methylcarbazic acid and one drop of sulfuric acid were added to 20 ml of methanol, and the reaction was carried out under heating and refluxing for 3 hours. After completion of the reaction, the reaction solution was allowed to cool to room temperature, and the precipitated crystals were collected by filtration to obtain 5.1 g of the desired product. ¹ H-NMR [CDCl ₃ / TMS, δ value (ppm)] 3.80 (3H, s.), 5.8 (2H, s.), 6.3 (1H, s.), 6.5 (1H, s.),
7.7 (1H, br.s.) 7.8 (1H, br.s). Yield: 95%

2-2. Methyl 2- (2-amino-
Production of (4,5-methylenedioxyphenylmethyl) carbazic acid.

Embedded image Methyl 2- (4,5-methylenedioxy-2-nitrophenylmethylidene) carbazate (4.0 g, 0.015 mol) obtained in 2-1 and 0.4 g of 5% palladium carbon were added to 100 ml of methanol. 3 ~
Hydrogenation was performed at 4 kg / m ² . After the theoretical amount of hydrogen was absorbed, the catalyst was filtered off from the reaction solution, and the solvent was distilled off under reduced pressure to obtain 3.6 g of the desired product. ¹ H-NMR [CDCl ₃ / TMS, δ value (ppm)] 3.73 (3H, s.), 3.90 (2H, s.), 3.6-4.2 (3H, br.), 5.84 (2
H, s.), 6.27 (1H, s.), 6.57 (1H, s.), 6.3 (1H, br.). Yield: quantitative

2-3. 3-methoxycarbonylamino-6,7-methylenedioxy-3,4-dihydro-2
Production of (1H) -quinazoline.

Embedded image Methyl 2- (2-amino-4,5- obtained in 2-2
Methylenedioxyphenylmethyl) carbazic acid 3.6
g (0.015 mol) and 2.6 g (0.0165 mol) of 1,1'-carbonylbis-1H-imidazole were dissolved in 20 ml of tetrahydrofuran, and reacted at room temperature for 3 hours. After completion of the reaction, the reaction solution is poured into 20 ml of water, the target substance is extracted with ethyl acetate, the extract is washed with water and saturated saline, dried over anhydrous magnesium sulfate, and the solvent is distilled off under reduced pressure. To 3.6
g was obtained. ¹ H-NMR [CDCl ₃ / TMS, δ value (ppm)] 3.7 (3H, s.), 4.37 (2H, s.), 5.93 (2H, s.), 6.0 (1H, s.),
6.6 (1H, s.), 7.4 (1H, s.), 7.7 (1H, s.). Yield: 90%

2-4. Production of 3-amino-6,7-methylenedioxy-3,4-dihydro-2 (1H) quinazolinone (Compound NoII-43).

Embedded image 3-methoxycarbonylamino-6 obtained in 2-3
7-methylenedioxy-3,4-dihydro-2 (1H)
2.65 g (0.01 mol) of quinazoline was dissolved in 20 ml of methanol, 4 ml of a 20% aqueous sodium hydroxide solution was added to the solution, and the mixture was reacted under heating and refluxing for 3 hours. After the completion of the reaction, the solvent was distilled off under reduced pressure, water was added to the residue to precipitate crystals, and the crystals were collected by filtration, and the obtained crude product was recrystallized from 95% methanol to give the desired product. 0.3 g were obtained. Physical properties: m. p. 211.0 ° C Yield: 6
2%

Embodiment 3 FIG. 3-1. 3-t-butoxycarbonylamino-3,4
Preparation of -dihydro-2 (1H) -quinazolithione.

Embedded image T-butyl 2- (2-aminophenylmethyl) carbazic acid produced in the same manner as in Examples 2-1 and 2-2
38 g (5 mmol) and 1.11 g triethylamine
(11.0 mmol) was dissolved in 20 ml of ether, cooled to -20 ° C, and 1.54 g of thiophosgene was added to the solution.
(5.25 mmol) was added dropwise in 30 minutes, and after completion of the addition,
The reaction solution is returned to room temperature, and the precipitated salt is removed by filtration. The filtrate is washed with water and saturated saline, dried over anhydrous magnesium sulfate, and the solvent is distilled off under reduced pressure. Recrystallization from ethyl ether gave 0.5 g of the desired product. ¹ H-NMR [CDCl ₃ / TMS, δ value (ppm)] 1.52 (9H, s.), 4.87 (2H, s.), 6.7 (1H, d.), 7.02-7.24 (4
H, m.), 8.15 (1H, br.s.). Yield: 35.8%

3-2. 3-Amino-3,4-dihydro-2 (1H) -quinazolithione (Compound NoII-47)
Manufacturing of.

Embedded image 3-t-butoxycarbonylamino- obtained in 3-1
3,4-dihydro-2 (1H) -quinazolythion 0.5
g (1.8 mmol) was added to 2 ml of trifluoroacetic acid and reacted at room temperature for 3 hours. After completion of the reaction, 10 ml of ethanol was added to the reaction solution, the solvent was distilled off under reduced pressure, and the obtained residue was reconstituted with methanol to obtain 0.35 g of the desired product. Physical properties: m. p. 174.0 ° C Yield 93.1
%

Embodiment 4 FIG. Production of 3- (3-pyridylmethylideneamino) -3,4-dihydro-2 (1H) quinazolinone (Compound No. 2).

Embedded image 0.4 g (2.5 mmol) of 3-amino-3,4-dihydro-2 (1H) -quinazolinone, 0.27 g (2.
(5 mmol) of nicotinic aldehyde and one drop of sulfuric acid were added to 10 ml of methanol, and the mixture was reacted under heating and reflux for 3 hours. After completion of the reaction, crystals precipitated in the reaction system were collected by filtration and dried to obtain 0.58 g of the desired product. Physical properties: m. p. 216.6-219.4 ° C. Yield: 9
2%

Embodiment 5 FIG. Production of 3- [1- (3-pyridylethylideneamino) -3,4-dihydro-2 (1H) quinazolinone (Compound No. 6)

Embedded image 0.4 g (2.5 mmol) of 3-amino-3,4-dihydro-2 (1H) quinazolinone, 0.31 g (2.5
Mmol) of 3-acetylpyridine and one drop of sulfuric acid.
The mixture was added to 0 ml of methanol and reacted under heating and reflux for 3 hours. After completion of the reaction, crystals precipitated in the reaction system were collected by filtration and dried to obtain 0.6 g of the desired product. Physical properties: m. p. 212.4-217.3 ° C Yield: 9
0%

Embodiment 6 FIG. Production of 3- (3-pyridylmethylideneamino) -3,4-dihydro-2 (1H) quinazolithione (Compound No. 120).

Embedded image 0.15 g (1.4 mmol) of 3-amino-3,4-dihydro-2 (1H) -quinazolithion, 0.15 g (1.4 mmol) of nicotinic aldehyde and one drop of sulfuric acid are added to 10 ml of methanol and heated. The reaction was performed for 3 hours under reflux. After the completion of the reaction, crystals precipitated in the reaction system were collected by filtration and dried to obtain 0.35 g of the desired product. Physical properties: m. p. 225.1 ° C. Yield 94.5%

Embodiment 7 FIG. Production of 3- (3-pyridylmethylamino) -3,4-dihydro-2 (1H) quinazolinone (Compound No. 409).

Embedded image 50 g of 1.26 g (5 mmol) of 3- (3-pyridylmethylideneamino) -3,4-dihydro-2 (1H) -quinazolinone and 0.2 g of 5% palladium carbon
and then hydrogenated at 3-4 kg / m ² . After the theoretical amount of hydrogen had been absorbed, the catalyst was filtered off from the reaction solution, the solvent was distilled off under reduced pressure, and a 20% aqueous sodium hydroxide solution was added to the residue to obtain ethyl acetate (20 ml ×
The extract was washed in 3), the extract was washed with water and saturated saline, dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The crude product obtained was re-used with ethyl acetate-methanol. Crystallization gave 1.14 g of the desired product. Physical properties: m. p. 144.2-150.0 ° C Yield: 9
0%

Embodiment 8 FIG. 1-methyl-3- (3-pyridylmethylideneamino) -3,4-dihydro-2 (1
H) Preparation of quinazolinone (Compound No. 236).

Embedded image 1.26 g (5 mmol) of 3- (3-pyridylmethylideneamino) -3,4-dihydro-2 (1H) -quinazolinone are dissolved in 20 ml of dimethylformamide and 0.21 g of sodium hydride are added to the solution. (62.4%) and reacted at room temperature for 30 minutes, then 0.85 g
(6 mmol) of methyl iodide was added and reacted for 3 hours. After completion of the reaction, the reaction solution was poured into ice water, the desired product was extracted with ethyl acetate (20 ml × 3), the extract was washed with water and saturated saline, dried over anhydrous magnesium sulfate, and then dried under reduced pressure to remove the solvent. The crude product obtained by distilling off the residue was purified by silica gel column chromatography to obtain 0.67 g of the desired product. Physical properties: m. p. 117 ° C Yield: 50%

Embodiment 9 FIG. Production of 1-methyl-3- (3-pyridylmethylamino) -3,4-dihydro-2 (1H) quinazolinone (Compound No. 411).

Embedded image 0.5 g (1.8 mmol) of 1-methyl-3- (3-
Pyridylmethylideneamino) -3,4-dihydro-2
(1H) -quinazolinone was dissolved in 10 ml of a 5% hydrogen chloride methanol solution, and 0.11 g of NaBH ₃ CN was added to the solution, followed by a reaction at room temperature for 3 hours. After completion of the reaction, the reaction mixture was poured into water, the pH of the mixture was adjusted to 9 with a 10% aqueous sodium hydroxide solution, the target substance was extracted with ethyl acetate (20 ml × 3), and the extract was washed with water and saturated saline. After drying over anhydrous magnesium sulfate, the crude product obtained by evaporating the solvent under reduced pressure was purified with ethyl acetate-methanol to obtain 0.15 g of the desired product. Physical properties: paste Yield: 30% ¹ H-NMR [CDCl ₃ / TMS, δ value (ppm)] 3.33 (3H, s.), 4.01 (3H, br.), 4.36 (2H, s.), 5.21 ( 1H, b
rt), 6.84 (1H, br.), 6.92-7.03 (2H, m.), 7.19-7.32 (2
H, m.), 7.68-7.76 (1H, m.), 8.15 (1H, br.), 8.62 (1H, s.).

Embodiment 10 FIG. 10-1. Production of 2- (2-nitrophenylmethylidene) nicotinic acid hydrazide.

Embedded image 3.33 g (22 mmol) of 2-nitrobenzaldehyde, 3.0 g (22 mmol) of nicotinic hydrazide
Then, one drop of sulfuric acid was added to 20 ml of methanol, and the reaction was carried out under reflux for 3 hours. After completion of the reaction, the reaction solution was cooled to room temperature, and the precipitated crystals were collected by filtration to obtain 5.34 g of the desired product. Physical properties: m. p. 251 ° C Yield: 90%

10-2. Production of 2- (2-aminophenylmethylidene) nicotinic acid hydrazide.

Embedded image 2.7 g (10 mmol) of 2- (2-nitrophenylmethylidene) nicotinic acid hydrazide obtained in 10-1 and 0.27 g of 5% palladium carbon were added to 20 ml of acetic acid to give 3 to 4 kg / d. Hydrogenation was performed in cm ² .
After the theoretical amount of hydrogen has been absorbed, the catalyst is removed by filtration from the reaction solution, and the solvent is distilled off under reduced pressure to obtain the desired product 2.35.
g was obtained. ¹ H-NMR [CDCl ₃ / TMS, δ value (ppm)] 6.58 (1H, t.), 6.75 (1H, d.), 7.07 (2H, s.), 7.12 (1H,
t.), 7.19 (1H, d.), 7.58 (1H, m.), 8.26 (1H, m.), 8.42 (1
H, s.), 8.70 (1H, m.), 9.04 (1H, d.), 11.9 (1H, br.). Yield: quantitative

10-3. Production of 2- (2-aminophenylmethyl) nicotinic hydrazide

Embedded image 10-2 obtained in 2- (2-aminophenyl methylidene) nicotinic acid hydrazide 1.2 g (5 mmol) and NaBH ₄ 0.38 g 5 hours reaction (10 mmol) in added 60 ° C. of water 10ml Was done. After completion of the reaction, 10 ml of a 10% aqueous sodium hydroxide solution was added to the reaction solution, and the desired product was extracted with ethyl acetate. The extract was washed with water and saturated saline, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. Evaporation gave 0.65 g of the desired product. ¹ H-NMR [CDCl ₃ / TMS, δ value (ppm)] 4.1 (2H, s.), 4.5 (2H, br.s.), 5.0 (1H, br.s.), 6.7 (2H,
m.), 7.0-7.2 (2H, m.), 7.35-7.4 (1H, m.), 7.97 (1H, s.),
8.03-8.07 (1H, m.), 8.76 (1H, m.), 8.78 (1H, m.). Yield: 54.1%

10-4. Production of 3- (3-pyridylcarbonylamino) -3,4-dihydro-2 (1H) -quinazoline (Compound No. 493).

Embedded image 2- (2-aminophenylmethyl) obtained in 10-3
0.6 g (2.4 mmol) of nicotinic acid hydrazide and 0.3 of 1,1'-carbonylbis-1H-imidazole
8 g (2.4 mmol) was dissolved in 10 ml of tetrahydrofuran and reacted at room temperature for 3 hours. After completion of the reaction, the reaction solution is poured into 20 ml of water, the target substance is extracted with ethyl acetate, the extract is washed with water and saturated saline, dried over anhydrous magnesium sulfate, and the solvent is distilled off under reduced pressure. Was recrystallized from methanol to obtain 0.5 g of the desired product. Physical properties: m. p. 221.1-224.0 ° C Yield: 7
8.1%

The pest control agent containing the substituted aminoquinazolinone (thione) derivative represented by the general formula (I) of the present invention as an active ingredient can be used in various agricultural and forestry which damages rice, vegetables, fruit trees, other crops, flowers and the like. It is suitable for pest control such as horticulture, storage pests, sanitary pests and nematodes.
rvata lugens), stag beetle (Sogatella furcifera)
), Citrus whitefly (Diaphorina citri), citrus whitefly (Dialeurodes citri), tobacco whitefly (Be
misia tabaci), whiteflies (Trialeurodes v
aporariorum), radish aphids (Brevicoryne br)
assicae), cotton aphid (Aphis gossypii), wheat aphid (Rhopalosiphum padi), peach peach aphid (Myzus persicae), hornworm (Ceroplastes)
ceriferus), Peanut (Pulvinaria a)
urantii), Citrus roundworm (Pseudaonidia)
duplex), pear scale insect (Comstockaspis pern
iciosa), Unaspis yanonensis
Hemiptera pests such as the southern nematode (Pratylen
chus coffeae), potato cyst nematode (Globod)
era rostochiensis), root-knot nematode (Meloidogyn)
e sp.), tangerine nematode (Tylenchulus semipene)
trans), Acacia chinensis (Aphelenchus aven)
ae), Hagare nematode (Aphelenchoides ritzemabos)
It also has an insecticidal effect against the nematodes of the order Nematodes such as i). The scientific names are based on the 1987 Agricultural and Forestry Pests and Insects Directory (edited by the Japan Society of Applied Animal Entomology).

The pest controlling agent of the present invention containing a substituted aminoquinazolinone (thione) derivative represented by the general formula (I) or a salt thereof as an active ingredient damages paddy fields, fruit trees, vegetables, other crops and flowers and the like. It has a significant insecticidal effect on the pests or sanitary pests that
In accordance with the time when pests are predicted to occur, before or when the occurrence of pests is confirmed, paddy fields, fruit trees, vegetables, other crops, flowers and other paddy water, foliage, soil, etc. and sanitary pests The intended effect of the insecticide of the present invention can be achieved by treating the pests, which are expected to occur or cause damage to humans and animals, to the interior of a house or a ditch around a house. The invention is not limited to only these embodiments.

When the substituted aminoquinazolinone (thione) derivative represented by the general formula (I) of the present invention or a salt thereof is used as a pesticidal agent, it can be obtained by a conventional method for pesticide preparations.
It is common to formulate and use it in a convenient form. That is, the substituted aminoquinazolinone (thione) derivative represented by the general formula (I) or a salt thereof according to the present invention can be prepared by adding them to a suitable inert carrier or, if necessary, together with an auxiliary in a suitable ratio. Compound, dissolve, separate, suspend, mix, impregnate, adsorb or adhere, and formulate into appropriate dosage forms such as suspensions, emulsions, solutions, wettable powders, granules, powders, tablets, etc. Good. The inert carrier that can be used in the present invention may be either solid or liquid. Examples of the material that can be a solid carrier include soybean flour, cereal flour, wood flour, bark flour, saw flour, and tobacco stem flour. , Walnut shell powder, bran,
Cellulose powder, residue after extraction of plant extract, synthetic polymer such as pulverized synthetic resin, clays (eg, kaolin, bentonite, acid clay), talcs (eg, talc, pyrophyllide, etc.), silicas (eg, diatomaceous earth, silica sand) , Mica, white carbon [Synthetic high-dispersion silicic acid, also called hydrous fine silicon or hydrous silicic acid, some of which contain calcium silicate as a main component.]), Activated carbon, sulfur powder, pumice, calcined diatomaceous earth, crushed bricks, Fly ash, sand,
Inorganic mineral powders such as calcium carbonate and calcium phosphate,
Examples include chemical fertilizers such as ammonium sulfate, phosphorous ammonium, ammonium nitrate, urea, and salt ammonium, and compost, and these are used alone or in the form of a mixture of two or more.

The material that can be a liquid carrier is selected from those having a solvent function per se, and those capable of dispersing the active ingredient compound with the aid of an adjuvant even without the solvent function. The following carriers can be exemplified as typical examples. These carriers are used alone or in the form of a mixture of two or more, and include, for example, water, alcohols (eg, methanol, ethanol, isopropanol, butanol, ethylene glycol and the like), Ketones (eg, acetone, methyl ethyl ketone, methyl isobutyl ketone,
Diisobutyl ketone, cyclohexanone, etc.), ethers (eg, ethyl ether, dioxane, cellosolve,
Dipropyl ether, tetrahydrofuran, etc.), aliphatic hydrocarbons (eg, kerosene, mineral oil, etc.), aromatic hydrocarbons (eg, benzene, toluene, xylene, solvent naphtha, alkylnaphthalene, etc.), halogenated hydrocarbons (eg, dichloroethane) , Chloroform, carbon tetrachloride, etc.), esters (eg, ethyl acetate, diisopropyl phthalate, dibutyl phthalate, dioctyl phthalate), amides (eg, dimethylformamide, diethylformamide, dimethylacetamide, etc.), nitriles (eg, acetonitrile, etc.) ), Dimethylsulfoxides and the like.

Examples of the other auxiliaries include the following typical auxiliaries. These auxiliaries are used according to the purpose, and may be used alone or in combination of two or more. In some cases, however, it is possible to use no auxiliaries. Surfactants are used for the purpose of emulsifying, dispersing, solubilizing and / or wetting the active ingredient compound, for example, polyoxyethylene alkyl ether, polyoxyethylene alkyl aryl ether, polyoxyethylene higher fatty acid ester, polyoxyethylene Resin acid ester, polyoxyethylene sorbitan monolaurate, polyoxyethylene sorbitan monooleate, alkyl aryl sulfonate, naphthalene sulfonic acid condensate,
Surfactants such as lignin sulfonate and higher alcohol sulfate can be exemplified.

For the purpose of stabilizing the dispersion of the active ingredient compound, sticking and / or binding, the following auxiliaries can be used. For example, casein, gelatin, starch,
Auxiliaries such as methylcellulose, carboxymethylcellulose, gum arabic, polyvinyl alcohol, pine oil, bran oil, bentonite, and lignin sulfonate can also be used. The following auxiliaries can be used to improve the flowability of the solid product. For example, auxiliaries such as wax, stearate, alkyl phosphate and the like can be used. As peptizers for suspension products, auxiliary agents such as, for example, naphthalenesulfonic acid condensates, condensed phosphates and the like can also be used. As an antifoaming agent, for example, an auxiliary agent such as silicone oil can be used. The compounding ratio of the active ingredient compound can be adjusted according to need. For example, 0.01 to 50% by weight in the case of powder or granules, and 0.01 to 50% in the case of emulsion or wettable powder. % By weight is appropriate.

The pest controlling agent of the present invention containing a substituted aminoquinazolinone (thione) derivative represented by the general formula (I) or a salt thereof as an active ingredient is useful for controlling various pests.
An amount effective for controlling pests may be used as it is, or appropriately diluted or suspended with water or the like, and applied to the pest or a place where the generation or growth of the pest is not preferable. The amount of the pesticidal agent containing the substituted aminoquinazolinone (thione) derivative represented by the general formula (I) of the present invention or a salt thereof as an active ingredient depends on various factors, for example, the purpose, the target pest, the growth status of the crop, It varies depending on the tendency of pests, weather, environmental conditions, dosage form, method of application, place of application, time of application, etc., provided that the active ingredient is appropriately selected from the range of 0.01 g to 5 kg per 10 ares according to the purpose. good. The pest control agent containing the substituted aminoquinazolinone (thione) derivative represented by the general formula (I) of the present invention or a salt thereof as an active ingredient is further used for controlling pests to be controlled, extending the suitable period of control, or reducing the dosage. It can be used in combination with other insecticides or fungicides for measuring purposes.
Hereinafter, typical formulation examples and test examples of the present invention are shown, but the present invention is not limited thereto. In addition, in the formulation examples, "parts" indicates parts by weight.

Formulation Example 1 Compounds listed in Tables 2, 4 and 6 50 parts Xylene 40 parts Mixture of polyoxyethylene nonylphenyl ether and calcium alkylbenzenesulfonate 10 parts The above are uniformly mixed and dissolved to form an emulsion. Formulation example 2. Compounds listed in Tables 2, 4 and 6 3 parts Clay powder 82 parts Diatomaceous earth powder 15 parts The above are uniformly mixed and pulverized to obtain a powder.

Formulation Example 3 Compounds listed in Tables 2, 4 and 6 5 parts Mixed powder of bentonite and clay 90 parts Calcium ligninsulfonate 5 parts The above components were uniformly mixed, kneaded by adding an appropriate amount of water, and granulated.
Dry to granules. Formulation Example 4. Compounds described in Tables 2, 4 and 6 20 parts Kaolin and synthetic highly dispersed silicic acid 75 parts Mixture of polyoxyethylene nonylphenyl ether and calcium alkylbenzenesulfonate 5 parts I do.

Test Example 1 Peach aphid ( Myzu s
persicae ) The control value test was carried out on a plastic pot having a diameter of 8 cm and a height of 8 cm, Chinese peach aphids were bred and the number of parasites in each pot was examined. The substituted aminoquinazoline (thione) derivative represented by the general formula (I) of the present invention or a salt thereof is dispersed in water, diluted to 500 ppm of a drug solution, and the drug solution is planted in a pot, sprayed on the leaves of Chinese cabbage and air-dried. The pots were stored in a greenhouse, and on the 6th day after spraying the medicine, the number of peach aphid parasites infesting each Chinese cabbage was investigated, the control value was calculated from the following formula, and the judgment was made according to the following criteria. . Control value = 100 − {(T × Ca) / (Ta × C)} × 100 Ta: Number of parasites before application in the treated area T: Number of parasites after application in the treated area Ca: Parasite before application in the untreated area Number C: number of parasites after application in untreated plots Criteria. A: Control value 100% B: Control value 99% to 90% C: Control value 89% to 80% D: Control value 79% to 50%

Test Example 2 Brown planthopper (Nilaparvata)
Insecticidal test against L. lugens) The substituted aminoquinazoline (thione) derivative represented by the general formula (I) of the present invention or a salt thereof is dispersed in water for 500 minutes.
The rice seedlings (variety: Nipponbare) were immersed in the chemical solution for 30 seconds, air-dried, placed in a glass test tube, inoculated with 10 plants of the third planthopper, and plugged with cotton. After a day, the number of live and dead insects was investigated, and the mortality was calculated by the following formula, and the judgment was made according to the following judgment criteria. Corrected mortality (%) = {(survival rate of untreated section−survival rate of treated section) / (survival rate of untreated section)} × 100 Criteria: Same as in Test Example 1.

As a result, a pesticidal composition containing a substituted aminoquinazoline (thione) derivative represented by the general formula (I) of the present invention as an active ingredient was prepared. 2, 3, 4, 6, 16, 1
9, 20, 35, 45, 98, 120, 235, 23
6, 256, 268, 269, 271, 272, 27
3, 274, 275, 276, 283, 284, 28
5, 288, 289, 295, 297, 298, 30
0, 368, 369, 370, 371, 372, 37
3, 374, 375, 376, 377, 378, 37
9, 380, 381, 382, 383, 384, 38
5, 386, 387, 472, 473, 474, 47
5, 476, 477, 478, 479, 480, 48
1,482,483,484,485,486,48
Compounds 7, 488, 489, 490, 491 show an insecticidal effect on peach aphids D or higher, especially 2, 3, 4, 6, 19, 20, 35, 98, 120, 2
35, 236, 256, 268, 269, 271, 27
2, 273, 274, 275, 276, 283, 28
4, 285, 288, 289, 295, 297, 29
8, 300, 368, 369, 370, 371, 37
2,373,374,375,376,377,37
8, 379, 380, 381, 382, 383, 38
4, 385, 386, 387, 473, 474, 47
5,476,477,478,479,481,48
2,483,484,485,486,487,48
8, 489, 490, 491, 491.1-491.6
The compound of No. showed an excellent insecticidal effect of A.

Compound No. against brown planthopper
2, 3, 4, 7, 19, 20, 35, 45, 98, 12
0, 236, 268, 269, 272, 273, 28
8, 298, 300, 389, 370, 371, 37
2, 374, 375, 376, 380, 381, 38
2,383,384,387,472,474,47
7,479,481,482,484,386,47
3, 475, 480, 483, 486, 487, 48
8, 489, 490, 491, 491.1-491.6
Shows an insecticidal effect of D or more, particularly 3, 19, 35, 23
6, 269, 273, 381, 382, 386, 47
3, 475, 480, 483, 486, 489, 49
Compounds 0, 491, 491.1 to 491.6 show the excellent insecticidal effect of A.

────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. ⁷ Identification code FI C07D 403/12 C07D 403/12 405/12 405/12 417/12 417/12 (56) References JP-A-51-54923 ( JP, A) Journal of Heterocyclic Chemistry; vol. 21 (No. 6) p1709-1711 (1984) (58) Fields investigated (Int. Cl. ⁷ , DB name) C07D 401/12 A01N 43/54 A01N 43/78 C07D 239/78 C07D 239/80 C07D 403 / 12 C07D 405/12 C07D 417/12 CA (STN) REGISTRY (STN)

Claims (6)

(57) [Claims] 1. A compound of the general formula (I) Wherein R is a hydrogen atom, a hydroxyl group, a formyl group, (C _1-12 )
Alkyl group, halo (C _1-6 ) alkyl group, hydroxy (C _1-6 )
Alkyl group, (C _2-6 ) alkenyl group, (C _2-6 ) alkynyl group, (C _1-6 ) alkoxy group, halo (C _1-6 ) alkoxy group, (C
_1-6 ) alkoxy (C _1-3 ) alkyl group, (C _1-6 ) alkoxy (C
_1-3 ) alkoxy (C _1-3 ) alkyl group, (C _1-6 ) alkylthio group, halo (C _1-6 ) alkylthio group, (C _1-6 ) alkylsulfinyl group, (C _1-6 ) alkyl Sulfonyl group, (C _1-6 ) alkylthio (C _1-3 ) alkyl group, di (C
_1-6) alkoxy (C _1-3) alkyl group, amino (C _1-6) may alkyl groups, the same or different, (C _1-6) alkyl groups, halo (C _1-6) alkyl group, (C _2-6 ) alkenyl group, or (C _2-6 )
Amino (C _1-6 ) alkyl group having 1 to 2 substituents selected from alkynyl group, cyano (C _1-6 ) alkyl group, (C
_1-6) alkylcarbonyl group, (C _1-6) alkoxycarbonyl group, hydroxycarbonyl (C _1-3) alkyl groups, (C _1-6)
Alkoxycarbonyl (C _1-3 ) alkyl group, aminocarbonyl group, which may be the same or different, (C _1-6 ) alkyl group,
(C _2-6 ) alkenyl group, or (C _2-6 ) aminocarbonyl group having one or two substituents selected from alkynyl group,
(C _3-6 ) cycloalkyl (C _1-3 ) alkyl group, phenyl (C
_1-3 ) alkyl group, which may be the same or different, halogen atom, nitro group, cyano group, (C _1-6 ) alkyl group, halo (C
_{1-6 selected from} an alkyl group, a (C _1-6 ) alkoxy group, a halo (C _1-6 ) alkoxy group, a (C _1-6 ) alkylthio group, or a halo (C _1-6 ) alkylthio group A phenyl (C _1-3 ) alkyl group having from 5 to 5 substituents on the ring, a phenylcarbonyl group, which may be the same or different, a halogen atom, a nitro group, a cyano group, a (C _1-6 ) alkyl group, Halo (C _1-6 ) alkyl group, (C _1-6 ) alkoxy group, halo (C _1-6 ) alkoxy group, (C
_1-6 ) an alkylthio group, or a phenylcarbonyl group having 1 to 5 substituents on the ring selected from a halo (C _1-6 ) alkylthio group, a phenylthio group, which may be the same or different, a halogen atom, Nitro group, cyano group, (C _1-6 ) alkyl group, halo (C _1-6 ) alkyl group, (C _1-6 ) alkoxy group, halo (C _1-6 ) alkoxy group, (C _1-6 ) A phenylthio group or a phenylsulfonyl group having 1 to 5 substituents selected from an alkylthio group or a halo (C _1-6 ) alkylthio group on the ring, which may be the same or different, a halogen atom, a nitro group, a cyano group; Group, (C _1-6 ) alkyl group, halo (C _1-6 ) alkyl group, (C _1-6 ) alkoxy group, halo (C _1-6 ) alkoxy group, (C
_1-6) alkylthio group, or a halo (C _1-6) phenylsulfonyl group having 1 to 5 substituents selected from alkylthio groups on the ring, phenyl (C _1-6) alkylsulfonyl group ,, same Or may be different, a halogen atom, a nitro group, a cyano group, a (C _1-6 ) alkyl group, a halo (C _1-6 ) alkyl group, a (C _1-6 ) alkoxy group, a halo (C _1-6 ) Alkoxy group, (C
_1-6 ) phenyl having 1 to 5 substituents on a ring selected from an alkylthio group or a halo (C _1-6 ) alkylthio group
(C _1-6 ) alkylsulfonyl group, phenyloxycarbonyl group, which may be the same or different, a halogen atom, a nitro group, a cyano group, a (C _1-6 ) alkyl group, a halo (C _1-6 ) alkyl group, (C _1-6 ) alkoxy group, halo (C _1-6 ) alkoxy group, (C
_1-6 ) an alkylthio group, or a phenyloxycarbonyl group having 1 to 5 substituents selected from a halo (C _1-6 ) alkylthio group on the ring, a phenyloxy (C _1-3 ) alkyl group, identical Or may be different, a halogen atom, a nitro group, a cyano group, a (C _1-6 ) alkyl group, a halo (C _1-6 ) alkyl group, a (C _1-6 ) alkoxy group, a halo (C _1-6 ) Alkoxy group, (C
_1-6 ) an alkylthio group, or a phenyloxy (C _1-3 ) alkyl group having 1 to 5 substituents on the ring selected from a halo (C _1-6 ) alkylthio group, phenyl (C _2-6 ) Alkenyl group, which may be the same or different, a halogen atom, a nitro group, a cyano group, a (C _1-6 ) alkyl group, a halo (C _1-6 ) alkyl group, a (C _1-6 ) alkoxy group, a halo ( C _1-6 ) alkoxy group, (C
_1-6 ) alkylthio group, halo (C _1-6 ) alkylthio group, or
A phenyl (C _2-6 ) alkenyl group having 1 to 5 substituents selected from (C _1-2 ) alkylenedioxy groups on the ring, a phenyl (C _2-6 ) alkynyl group, the same or different Well,
Halogen atom, nitro group, cyano group, (C _1-6 ) alkyl group, halo (C _1-6 ) alkyl group, (C _1-6 ) alkoxy group, halo
(C _1-6 ) alkoxy group, (C _1-6 ) alkylthio group, halo (C
_1-6 ) an alkylthio group, or a phenyl ( _C2-4 ) alkynyl ( _C1-3 ) alkyl group having 1 to 5 substituents on the ring selected from ( _C1-2 ) alkylenedioxy groups A 1,3-dioxolan-2-yl (C _1-3 ) alkyl group, or phthalimide
(C _1-6 ) represents an alkyl group. R ¹ may be the same or different and is 1 selected from an oxygen atom, a sulfur atom or a nitrogen atom
A 5- to 6-membered heterocyclic group having up to 3 heteroatoms,
The heterocyclic groups may be the same or different, a halogen atom,
Cyano group, (C _1-6 ) alkyl group, halo (C _1-6 ) alkyl group,
Alternatively, it may have 1 to 5 substituents selected from (C _1-6 ) alkoxy groups, and the nitrogen atom in the heterocyclic group may represent an N-oxide group. Y represents an oxygen atom or a sulfur atom, and Z represents -N = C (R ² )-(where R ² is a hydrogen atom, a (C _1-6 ) alkyl group or a halo (C
_1-6 ) represents an alkyl group. ), ## STR3 ## -N (R ³ ) -CH (R ² )-(wherein R ² is as defined above, R ³ is a hydrogen atom, a (C _1-6 ) alkyl group, a formyl group, C _1-3 ) alkylcarbonyl group,
A halo (C _1-3 ) alkylcarbonyl group and a (C _1-3 ) alkyldithiocarbonyl group. ) Or -N (R ³ ) -CO- (wherein R ³ is the same as described above), and X may be the same or different and is a halogen atom, a hydroxyl group, a nitro group, a cyano group. , (C _1-6 ) alkyl group, halo (C _1-6 ) alkyl group, (C _1-6 )
Alkoxy group, halo ( _C1-6 ) alkoxy group, ( _C1-3 ) alkylenedioxy group, hydroxycarbonyl group, ( _C1-6 ) alkoxycarbonyl group, ( _C2-6 ) alkenyloxycarbonyl group, ( C _2-6) alkynyloxy carbonyl group selection, aminocarbonyl group, which may be identical or different, (C _1-6) alkyl, (C _2-6) alkenyl group, or (from C _2-6) alkynyl group Or an aminocarbonyl group having 1 to 2 substituents, an amino group, or the same or different, (C
_1-6 ) an alkyl group, a ( _C2-6 ) alkenyl group, or an amino group having 1 to 2 substituents selected from a ( _C2-6 ) alkynyl group, and n is an integer of 0 to 4 Is shown. ] The substituted aminoquinazolinone (thione) derivative represented by 2. R is a hydrogen atom, a formyl group, a (C _1-12 ) alkyl group, a halo (C _1-6 ) alkyl group, a (C _2-6 ) alkenyl group, a (C _2-6 ) alkynyl group, (C _1-6 ) alkoxy group, halo (C
_1-6 ) alkoxy group, (C _1-6 ) alkoxy (C _1-3 ) alkyl group, (C _1-6 ) alkoxy (C _1-3 ) alkoxy (C _1-3 ) alkyl group, (C _{1- 6)} alkylthio groups, halo (C _1-6) alkylthio group, amino (C _1-6) may alkyl groups, the same or different, (C _1-6) alkyl groups, halo (C _1-6) alkyl group , (C _2-6 )
An alkenyl group, or an amino (C _1-6 ) alkyl group having 1 to 2 substituents selected from a (C _2-6 ) alkynyl group, a cyano (C _1-6 ) alkyl group, a (C _1-6 ) Alkylcarbonyl group,
(C _1-6 ) alkoxycarbonyl group, hydroxycarbonyl
(C _1-3 ) alkyl group, (C _1-6 ) alkoxycarbonyl (C _1-3 )
Alkyl group, (C _3-6 ) cycloalkyl (C _1-3 ) alkyl group,
A phenyl (C _1-3 ) alkyl group, which may be the same or different,
Halogen atom, nitro group, cyano group, (C _1-6 ) alkyl group, halo (C _1-6 ) alkyl group, (C _1-6 ) alkoxy group, halo
(C _1-6 ) alkoxy group, (C _1-6 ) alkylthio group, or halo
A phenyl (C _1-3 ) alkyl group having 1 to 5 substituents on the ring selected from (C _1-6 ) alkylthio groups, a phenylcarbonyl group, which may be the same or different, a halogen atom,
Nitro group, cyano group, (C _1-6 ) alkyl group, halo (C _1-6 ) alkyl group, (C _1-6 ) alkoxy group, halo (C _1-6 ) alkoxy group, (C _1-6 ) A phenylcarbonyl group having 1 to 5 substituents on the ring selected from an alkylthio group or a halo (C _1-6 ) alkylthio group, a phenylthio group, which may be the same or different, a halogen atom, a nitro group, a cyano group; Group, (C _1-6 )
Alkyl group, halo (C _1-6) alkyl, (C _1-6) alkoxy groups, halo (C _1-6) alkoxy groups, (C _1-6) alkylthio group,
Or a phenylthio group having 1 to 5 substituents selected from a halo (C _1-6 ) alkylthio group on the ring, phenyl (C
_2-6 ) alkenyl group, which may be the same or different, a halogen atom, a nitro group, a cyano group, a (C _1-6 ) alkyl group, a halo (C
_1-6 ) alkyl group, (C _1-6 ) alkoxy group, halo (C _1-6 ) alkoxy group, (C _1-6 ) alkylthio group, halo (C _1-6 ) alkylthio group, or (C _{1- 2} ) a phenyl ( _C2-6 ) alkenyl group having 1 to 5 substituents on the ring selected from an alkylenedioxy group, a phenyl ( _C2-6 ) alkynyl group, or may be the same or different, Halogen atom, nitro group, cyano group, (C _1-6 ) alkyl group, halo (C _1-6 ) alkyl group, (C _1-6 )
1 to 5 selected from an alkoxy group, a halo (C _1-6 ) alkoxy group, a (C _1-6 ) alkylthio group, a halo (C _1-6 ) alkylthio group, and a (C _1-2 ) alkylenedioxy group It indicates the number of phenyl (C _2-4) having a substituent on the ring alkynyl (C _1-3) alkyl group may be R ¹ are the same or different, is selected from oxygen atom, sulfur atom or nitrogen atom A 5- to 6-membered heterocyclic group having 1 to 3 heteroatoms, which may be the same or different and includes a halogen atom, a cyano group, a (C _1-6 ) alkyl group, a halo (C _{1 -6)} can be alkyl groups, or (C _1-6) having 1 to 5 substituents selected from alkoxy group, the nitrogen atom in the heterocyclic group may show N- oxide group. Y represents an oxygen atom or a sulfur atom; Z represents -N (R ³ ) -CH (R ² )-(wherein R ² represents a hydrogen atom or a (C _1-6 ) alkyl group; R ³
Represents a hydrogen atom, a (C _1-6 ) alkyl group, a formyl group, a (C _1-3 ) alkylcarbonyl group, a halo (C _1-3 ) alkylcarbonyl group, or a (C _1-3 ) alkyldithiocarbonyl group . )
X is the same or different, a halogen atom,
Hydroxyl group, nitro group, cyano group, (C _1-6 ) alkyl group, halo
(C _1-6 ) alkyl group, (C _1-6 ) alkoxy group, halo (C _1-6 ) alkoxy group, (C _1-3 ) alkylenedioxy group, hydroxycarbonyl group, (C _1-6 ) alkoxy Carbonyl group, (C _2-6 )
Alkenyloxycarbonyl group, (C _2-6 ) alkynyloxycarbonyl group, aminocarbonyl group, which may be the same or different, (C _1-6 ) alkyl group, (C _2-6 ) alkenyl group, or (C _{2- 6} ) an aminocarbonyl group having 1 to 2 substituents selected from an alkynyl group, an amino group, or the same or different, a (C _1-6 ) alkyl group, a (C _2-6 ) alkenyl group, Or 1-2 selected from (C _2-6 ) alkynyl groups
The substituted aminoquinazolinone (thione) derivative or a salt thereof according to claim 1, wherein the amino group has an integer of 0 to 4. 3. R is a hydrogen atom, a formyl group, a (C _1-12 ) alkyl group, a halo (C _1-6 ) alkyl group, a (C _2-6 ) alkenyl group, a (C _2-6 ) alkynyl group, (C _1-6 ) alkylthio group, halo
(C _1-6 ) alkylthio group, (C _1-6 ) alkylcarbonyl group,
(C _1-6 ) alkoxycarbonyl group, (C _1-6 ) alkoxycarbonyl (C _1-3 ) alkyl group, phenylcarbonyl group, which may be the same or different, halogen atom, nitro group, cyano group, (C _{1 -6} ) alkyl group, halo (C _1-6 ) alkyl group, (C _1-6 )
Phenylcarbonyl having 1 to 5 substituents on a ring selected from an alkoxy group, a halo (C _1-6 ) alkoxy group, a (C _1-6 ) alkylthio group, and a halo (C _1-6 ) alkylthio group A phenyl (C _2-6 ) alkenyl group, which may be the same or different, a halogen atom, a nitro group, a cyano group, a (C _1-6 ) alkyl group, a halo (C _1-6 ) alkyl group, a (C _{1 -6} ) an alkoxy group,
Halo (C _1-6 ) alkoxy group, (C _1-6 ) alkylthio group, halo
A phenyl (C _2-6 ) alkenyl group having 1 to 5 substituents on a ring selected from a (C _1-6 ) alkylthio group or a (C _1-2 ) alkylenedioxy group, and phenyl (C _{2 -6} ) alkynyl group, or the same or different, a halogen atom,
Nitro group, cyano group, (C _1-6 ) alkyl group, halo (C _1-6 ) alkyl group, (C _1-6 ) alkoxy group, halo (C _1-6 ) alkoxy group, (C _1-6 ) 1 selected from an alkylthio group, a halo (C _1-6 ) alkylthio group, and a (C _1-2 ) alkylenedioxy group
A phenyl (C _2-4 ) alkynyl (C _1-3 ) alkyl group having from 5 to 5 substituents on the ring, R ¹ represents a pyridyl group,
Represents an oxygen atom or a sulfur atom; Z represents -N (R ³ ) -CH (R ² )-(wherein R ² represents a hydrogen atom or a (C _1-6 ) alkyl group; ^Three
Represents a hydrogen atom or a (C _1-6 ) alkyl group. ) And X
May be the same or different, a halogen atom, a nitro group,
Cyano group, (C _1-6 ) alkyl group, halo (C _1-6 ) alkyl group,
(C _1-6 ) alkoxy group, halo (C _1-6 ) alkoxy group, (C _1-3 )
3. The substituted aminoquinazolinone (thione) derivative or a salt thereof according to claim 2, which represents an alkylenedioxy group or a (C _1-6 ) alkoxycarbonyl group, and n represents an integer of 0 to 4. 4. A compound of the general formula (II) [Wherein, X may be the same or different, and a halogen atom,
Hydroxyl group, nitro group, cyano group, (C _1-6 ) alkyl group, halo
(C _1-6 ) alkyl group, (C _1-6 ) alkoxy group, halo (C _1-6 ) alkoxy group, (C _1-3 ) alkylenedioxy group, hydroxycarbonyl group, (C _1-6 ) alkoxy Carbonyl group, (C _2-6 )
Alkenyloxycarbonyl group, (C _2-6 ) alkynyloxycarbonyl group, aminocarbonyl group, which may be the same or different, (C _1-6 ) alkyl group, (C _2-6 ) alkenyl group, or (C _{2- 6} ) an aminocarbonyl group having 1 to 2 substituents selected from an alkynyl group, an amino group, or the same or different, a (C _1-6 ) alkyl group, a (C _2-6 ) alkenyl group, Or 1-2 selected from (C _2-6 ) alkynyl groups
Represents an amino group having three substituents, n represents an integer of 0 to 4, and Y represents an oxygen atom or a sulfur atom. ] The compound represented by these. 5. A pesticidal composition comprising the substituted aminoquinazolinone (thione) derivative or a salt thereof according to any one of claims 1 to 3 as an active ingredient. 6. A pest control agent comprising the substituted aminoquinazolinone (thione) derivative or a salt thereof according to any one of claims 1 to 3 as an active ingredient for controlling pests per 10 ares. 0.01g-5
A method for controlling pests, which comprises treating kg.