JPH0525142A - Uracil derivative and noxious organism controlling agent - Google Patents

Abstract

PURPOSE:To provide a new uracil derivative having excellent insecticidal and miticidal activity against various agricultural vermin and spider mites and giving nearlyno adverse effect on mammals, fishes and beneficial insects. CONSTITUTION:The compound of formula I [R<1> is H, alkyl, alkenyl, formyl, alkylcarbonyl, benzyl, phenyl, etc.; R<2> is H, halogen, alkyl, SH, alkylthio, OH, alkoxy, CN, NO2, etc.; X is halogen, alkyl, alkoxy, NH2, CN, etc.; (l) is 0-5; Z<1> and Z<2> are O, S or NH; B is group of formula II (Y is halogen, alkyl, alkenyl, alkoxy, alkylthio, etc.; (m) is 0-5), naphthyl, furyl, etc.], e.g. 3-(difluoro-3,4-dioxymethylene-phenyl)-6-(2,6-difluorophenyl)-2,4(1H,3H)- pyrimidinedione. The objective compound wherein Z<2> is 0 can be produced by reaction of a compound of formula III successively with a compound of formula R<1>NH2 and a compound of formula B-NCZ<1> and cyclizing the obtained compound.

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to a novel uracil derivative and a pest control agent containing the derivative as an active ingredient.

[0002]

2. Description of the Related Art Conventionally, some patents and literatures have described uracil compounds. Journal of
American Chemical Society (J.Amer.Chem.So
c.), 58, 299 (1935), 3,6-diphenyluracil and 3-phenyl-6- (3-bromo-4-
Methoxyphenyl) uracil is described.

Further, the chemical abstract (Chem.A
b.), 52, 6364h (1958), 3,6-diphenyluracil is described. However, the above literature does not show any activity of these compounds against organisms.

[0004]

Due to the long-term use of insecticides, pests have acquired resistance in recent years, making it difficult to control them with conventional insecticides. In addition, some insecticides are highly toxic, and some are perturbing the ecosystem due to persistence. Therefore, the development of new insecticides with low toxicity and low residue is always expected.

[0005]

The present invention has the general formula [I]

[0006]

[Chemical 6]

In the formula, R ¹ is a hydrogen atom, C _{1 to} C ₄ alkyl group, C _{2 to} C ₄ alkenyl group, C _{2 to} C ₄ alkynyl group, C _{1 to} C ₄
Haloalkyl groups, C ₂ -C ₄ alkoxyalkyl group, formyl group, C ₂ -C ₆ alkylcarbonyl group, C ₂ -C ₆ alkoxycarbonyl group, C ₃ -C ₆ alkoxycarbonylalkyl group, C ₂ -C ₆ cyanoalkyl group, a benzyl group, a phenyl group, a cyano group, an amino group, C ₃ -C ₆ alkoxycarbonyl group, -SR ¹⁰ group {However, R ¹⁰ is C ₂ -C ₆ alkoxycarbonyl group, C ₁ -C ₆ alkylsulfonyl Basis, -NR ^1
1 R ¹² group (wherein R ¹¹ represents a C ₁ -C ₆ alkyl group, R ¹²
The C ₁ -C ₆ alkyl group, C ₂ -C ₆ alkoxycarbonyl group,
C ₃ -C ₉ alkoxycarbonylalkyl group, C ₁ -C ₆ alkylsulfonyl group, C ₂ -C ₆ alkylcarbonyl group, C ₃ -C ₉
A dialkylaminocarbonyl group, a C ₂ -C ₆ dialkylaminosulfonyl group or an unsubstituted or optionally substituted phenyl group), or an unsubstituted or optionally substituted phenyl group (however, optionally substituted) Good substituents include halogen atoms, cyano groups, nitro groups, C ₁
-C ₄ alkyl group, C ₁ -C ₄ haloalkyl groups, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy groups, C ₁ -C ₄ alkylthio group, C ₁ -C ₄ haloalkylthio group, C ₂ -C ₆ alkoxycarbonyl group, C ₂ -C ₆ haloalkoxycarbonyl groups, C ₂ -C ₆
An alkylcarbonyl group, a C _{2 to} C ₆ haloalkylcarbonyl group, a C _{1 to} C ₄ alkylsulfonyl group or a C _{1 to} C ₄ haloalkylsulfonyl group, and when two or more substituents are present, the substituents may be the same. May be different). }, Indicating an alkali metal or an alkaline earth metal,
R ² is a hydrogen atom, a halogen atom, a C _{1 to} C ₄ alkyl group, C ₁ to
C ₄ haloalkyl group, C ₁ -C ₄ hydroxyalkyl group, C ₂ ~
C ₄ alkoxyalkyl group, C ₂ -C ₄ alkylthioalkyl group, a thiol group, C ₁ -C ₄ alkylthio group, C ₁ -C ₄ alkylsulfinyl group, C ₁ -C ₄ alkylsulfonyl group, C ₁ ~
C ₄ haloalkylthio group, C ₁ -C ₄ haloalkylsulfinyl group, C ₁ -C ₄ haloalkylsulfonyl group, hydroxy group, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy group, a formyl group, a cyano group, A nitro group, an amido group or a thiocyanate group, Z ¹ and Z ² each independently represent an oxygen atom, a sulfur atom or an imino group, and X represents a halogen atom, C ₁
-C ₄ alkyl group, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio group, C ₁ -C ₄ haloalkyl groups, C ₁ -C ₄ haloalkoxy groups, C ₁ -C ₄ haloalkylthio group, an amino group , Cyano group,
Or represents a nitro group, and l is an integer of 0 to 5 (provided that 2 is
In the case of ~ 5, X may be the same or different)
And B is

[0008]

[Chemical 7]

[Wherein Y is a halogen atom, a C _{1 to} C ₆ alkyl group, a C _{2 to} C ₆ alkenyl group, a C _{2 to} C ₆ alkynyl group, a C ₃
To C ₆ cycloalkyl group, C _{1 to} C ₆ haloalkyl group, C _{2 to} C ₆
Haloalkenyl group, C ₂ -C ₆ haloalkynyl group, C ₃ -C ₆ halocycloalkyl group, C ₂ -C ₆ cyanoalkyl group, C ₁ -C ₆
Hydroxyalkyl group, C ₂ -C ₆ carboxyalkyl group,
C ₁ -C ₆ alkoxy group, C ₂ -C ₆ alkenyloxy group, C ₂ ~
C ₆ alkynyloxy group, C ₃ -C ₆ cycloalkyl group, C ₁ -C ₆ haloalkoxy group, C ₂ -C ₆ haloalkenyloxy group, C ₂ -C ₆ haloalkynyl group, C ₃ -C ₆ halo cycloalkoxy group, C ₄ -C ₇ halocycloalkyl alkoxy group, C ₁ -C ₆ alkylthio group, C ₂ -C ₆ alkenylthio group, C ₂ -C ₆ alkynylthio, C ₃ -C ₆ cycloalkylthio group , C _{1 to} C ₆ haloalkylthio group, C _{1 to} C ₆ alkylsulfinyl group, C _{2 to} C ₆ alkenylsulfinyl group, C _{2 to} C ₆
Alkynylsulfinyl group, C ₃ -C ₆ cycloalkyl alkylsulfinyl group, C ₁ -C ₆ haloalkylsulfinyl group, C ₁ ~
C ₆ alkylsulfonyl group, C ₂ -C ₆ alkenylsulfonyl group, C ₂ -C ₆ alkynylsulfonyl group, C ₃ -C ₆ cycloalkylsulfonyl group, C ₁ -C ₆ haloalkylsulfonyl group,
C ₂ -C ₆ alkoxyalkyl group, C ₂ -C ₆ alkoxyalkoxy, C ₂ -C ₆ haloalkoxyalkyl group, C ₂ -C ₆ haloalkoxy alkoxy group, C ₂ -C ₆ alkylthioalkyl group, C ₂ ~ C ₆ alkylthioalkoxy group, C ₃ -C ₆ alkoxycarbonylalkyl group, C ₃ -C ₆ alkylcarbonyl group, C ₂ -C ₆ alkoxycarbonyloxy group, C ₂ ~
C ₆ alkylcarbonyloxy group, C ₂ -C ₆ alkylcarbonyl group, C ₃ -C ₆ alkenylcarbonyl group, C ₃ -C ₆ alkynyl group, C ₄ -C ₇ cycloalkylcarbonyl group, C ₂ -C ₆ haloalkyl carbonyl group, C ₂ -C ₆ alkoxycarbonyl group, C ₂ -C ₆ haloalkoxycarbonyl groups,
C ₃ -C ₆ alkoxycarbonylalkoxy group, a nitro group,
Cyano group, hydroxy group, carboxyl group, thiocyanate group, isothiocyanate group, C ₂ -C ₆ thiocyanate alkyl group, C ₁ -C ₆ alkylsulfonyloxy group, C ₂ ~
C ₆ alkylthiocarbonyl group, amino group (-NR ³ R ⁴ ), aminocarbonyl group (-CONR ³ R ⁴ ), aminocarbonyloxy group
(-OCONR ³ R ⁴ ), amide group (-NR ³ COR ⁴ ), alkoxycarbonylamino group (-NR ³ CO ₂ R ⁴ ), aminosulfonyl group (-SO ₂ N
R ³ R ⁴ ), thioamide group (-NR ³ CSR ⁴ ), methylenedioxy group, halomethylenedioxy group, ethylenedioxy group, haloethylenedioxy group, trimethylsilyl group or

[0010]

[Chemical 8]

{However, W is

[0012]

[Chemical 9]

Or

[0014]

[Chemical 10]

(However, R ³ and R ⁴ are each independently a hydrogen atom, a C _{1 to} C ₆ alkyl group, a C _{2 to} C ₆ alkenyl group, a C _{2 to} C ₆
Alkynyl group, C ₁ -C ₆ haloalkyl group, C ₂ -C ₆ haloalkenyl group, C ₂ -C ₆ haloalkynyl group, C ₂ -C ₆ alkylcarbonyl group, C ₂ -C ₆ alkoxycarbonyl group, a phenyl group or A benzyl group, R ⁵ and R ⁶ each independently represent a hydrogen atom, a halogen atom, a C ₁ -C ₆ alkyl group, a C ₃ -C ₆ cycloalkyl group, a cyano group or a phenyl group, and q
Represents an integer of 0 to 2. ), N is an integer of 0 or 1, Ar is an unsubstituted or optionally substituted phenyl group, naphthyl group, furyl group, thienyl group, pyrrolyl group, pyrazolyl group, imidazolyl group, thiazolyl group, isothiazolyl Group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiadiazolyl group, triazolyl group, pyridyl group, pyridazyl group, pyrimidyl group, pyrazyl group, quinolyl group or quinoxalyl group (however,
As the substituent which may be substituted, a halogen atom, a cyano group, a nitro group, a C _{1 to} C ₄ alkyl group, a C _{1 to} C ₄ haloalkyl group, a C _{1 to} C ₄ alkoxy group, and a C _{1 to} C ₄ haloalkoxy group. , C _{1 to} C ₄ alkylthio group, C _{1 to} C ₄ haloalkylthio group, C _{1 to} C ₄ alkylsulfonyl group, C _{1 to} C ₄ haloalkylsulfonyl group, C _{2 to} C ₄ alkoxycarbonyl group, carboxyl group, amino group , Mono C ₁ -C ₄ alkylamino group, di
C ₁ -C ₄ alkylamino group, a phenyl group, a benzyl group, a methylenedioxy group or halo methylenedioxy group, the substituent when the substituent is two or more may be different even in the same ) Is shown. }, And m is an integer of 0 to 5 (provided that Y ¹ may be the same or different in the case of 2 to 5). ] Or an unsubstituted or optionally substituted naphthyl group, a furyl group, a thienyl group,
Pyrrolyl group, pyrazolyl group, imidazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, thiadiazolyl group, oxadiazolyl group, triazolyl group, pyridyl group, pyridazyl group, pyrimidyl group, pyrazyl group, quinolyl group, quinoxalyl group, benzofuryl group , A benzothienyl group, an indolyl group, a benzoxazolyl group or a benzothiazolyl group (however, a substituent which may be substituted is a halogen atom, a cyano group, a nitro group, a C ₁ -C ₄ alkyl group, C ₁ -C ₄ haloalkyl group, C _{1 to} C ₄ alkoxy group, C _{1 to} C ₄ haloalkoxy group, C ₁
~ C ₄ alkylthio group, C ₁ ~ C ₄ haloalkylthio group, C ₁ ~
C ₄ alkylsulfonyl group, C _{1 to} C ₄ haloalkylsulfonyl group, C _{2 to} C ₄ alkoxycarbonyl group, carboxyl group, amino group, mono C _{1 to} C ₄ alkylamino group, di C _{1 to} C ₄
An alkylamino group, a phenyl group, a phenoxy group or a benzyl group, and when two or more substituents are present, the substituents may be the same or different), and X ₁ is a hydrogen atom or 3- The present invention relates to a uracil derivative represented by "Brom-4-methoxy except when B is a phenyl group" and a pest control agent containing one or more of the derivatives as an active ingredient.

In the present invention, the pest control agent means especially a pest control agent. The compounds of the present invention are effective against various harmful pests at extremely low drug concentrations. Examples of the pest include agricultural pests such as green leafhoppers, brown planthoppers, green peach aphids, mosquitosus alba, Echinochloea lucidum, Kobnomeiga, and Koga moth, spider mites, mandarin mites, kanzawa mites, etc.
Sanitary pests such as fleas and lice, storage weevil such as brood weevils, stag beetles, and house moths, house pests such as termites, domestic pests such as mites, fleas, lice, indoor dust mites such as mites, leopard mites, and tick mites , Slugs, snails and other mollusks. That is, the compound of the present invention, Orthoptera, hemiptera, Lepidoptera, Coleoptera,
It can effectively control pests of Hymenoptera, Diptera, Termites, and mites and lice at low concentrations. On the other hand, it was found that the compound of the present invention is a very useful compound having almost no adverse effect on mammals, fish, crustaceans and beneficial insects, and completed the present invention.

Next, a method for producing the compound of the present invention will be described. The compound of the present invention is a novel uracil derivative. The synthesis method is, for example, Comprehensive Heterocyclic C
The uracil skeleton can be synthesized with reference to the synthetic method described in Hemistry, Vol. 3, p. 57 (1984) and the like. The manufacturing method including the above method will be specifically described.

[0018]

[Chemical 11]

[0019]

[Chemical 12]

[0020]

[Chemical 13]

[0021]

[Chemical 14]

[0022]

[Chemical 15]

[0023]

[Chemical 16]

In the formulas (methods A to I), R ¹ , R ² ,
X ₁ , B, Z ¹ and Z ² have the same meanings as described above, R ⁷ and R ⁸ each independently represent a C _{1 to} C ₆ alkyl group, a benzyl group or a phenyl group, and R ⁹ is a halogen atom. Represents a nitro group or a thiocyanate group, L ¹ is a halogen atom,
A good leaving group such as a methanesulfonate group, a p-toluenesulfonate group or a C _{1 to} C ₄ alkylsulfate group is shown, M ¹ is a sodium atom, a potassium atom or a copper atom, and hal is a chlorine atom or a bromine atom. Alternatively, it represents an iodine atom. In addition, formula [VII], formula [IX], formula [XIX], formula [X
X], formula [XXI], formula [XXII], formula [XXIII] and formula [XXV] are the compounds of the present invention.

Method A is a method suitable for the synthesis of R ² as a hydrogen atom or a C ₁ -C ₄ alkyl group. The starting material of formula [II] is the journal of heterocyclic chemistry (JH
eterocyclic Chem.), vol. 9, p. 513 (1972) and the like, and can be synthesized by a known method. In step 1, the compound of formula [II] can be easily obtained in good yield by reacting the compound of formula [II] with ammonia or ammonia acetate in the presence of acetic acid in the presence of acetic acid.

In step 2, the compound of formula [III] and the iso (thio) cyanate of formula [IV] or the (thio) carbamic acid ester of formula [V] are added in the presence of a base in an inert solvent. By reacting, the compound of the present invention of the formula [VII] can be obtained without isolating the intermediate [VI]. Examples of the base used include alkali metal alkoxides such as sodium ethoxide, alkali metal hydroxides such as sodium hydroxide and potassium hydroxide, alkali metal carbonates such as sodium carbonate and potassium carbonate, or sodium hydride. . As the solvent, lower alcohols such as methanol and ethanol, benzene,
Aromatic hydrocarbons such as toluene, ethers such as diethyl ether, tetrahydrofuran, 1,4-dioxane, 1,2-dimethoxyethane and 1,2-diethoxyethane, halogenation of dichloromethane, 1,2-dichloroethane, etc. Examples thereof include hydrocarbons, amides such as dimethylformamide and dimethylacetamide, acetonitrile, dimethylsulfoxide, and mixed solvents thereof. Generally, sodium alkoxide (R ⁷ ONa) is used as a base in the same alcohol (R ⁷ OH) solvent as R ⁷ of the formula [III], or hydrogenated as a base in a tetrahydrofuran, dimethylformamide or dimethylsulfoxide solvent. Preference is given to using sodium. The reaction temperature can be set to any temperature from −60 ° C. to the reflux temperature of the reaction mixture.

In step 3, the compound of formula [VII] is reacted with the compound of formula [VIII] in the presence of a base in an inert solvent to obtain the compound of the formula [IX]. . When R ¹ is a C _{1 to} C ₄ alkyl group, a C _{2 to} C ₄ alkenyl group, a C _{2 to} C ₄ alkynyl group or a C _{2 to} C ₄ alkoxyalkyl group, as R ¹ -L ^{1 in} formula (VIII) It is preferable to use halides such as chloride and bromide.
When R ¹ is a C ₁ -C ₄ alkyl group, dialkyl sulfate (R
¹ ₂ SO ₄ ) is also suitable. The base used is preferably an alkali metal alkoxide such as sodium ethoxide, an alkali metal carbonate such as sodium carbonate or potassium carbonate, or sodium hydride. As the solvent, water, lower alcohols such as ethanol, ethers such as 1,2-dimethoxyethane and tetrahydrofuran, dimethylformamide or dimethylsulfoxide are preferable.
The reaction temperature can be set to any temperature from 0 ° C to the reflux temperature of the reaction mixture, but is preferably 0 ° C to 30 ° C. When R ¹ is formyl, R ¹ -L ¹ is formic acid halide, and when it is a C ₂ -C ₆ alkylcarbonyl group, R ¹ -L ¹ is C ₂ -C ₆ alkanoic acid halide or anhydride, C ₂ preferably, in the case of -C ₆ alkoxycarbonyl group using a C ₂ -C ₆ alkyl chloroformate or bromo formate as R ¹ -L ^1. Sodium hydride is preferred as the base used. However, in the case of introducing a C ₂ -C ₆ alkylcarbonyl group with an acid anhydride can be carried out the reaction without using a base. The solvent is preferably dimethylformamide or dimethylsulfoxide. The reaction temperature can be set to any temperature from 0 ° C to the reflux temperature of the reaction mixture, but it is preferably carried out at 0 ° C to 30 ° C.

Alkylation of compounds of formula [VII] where Z ¹ is a sulfur atom usually produces a mixture of N- and S-alkylated products. Desired N-C ₁ ~C ₄ alkyl -, N-C ₂ ~C ₄ alkenyl -, N-C ₂ ~C ₄ alkynyl -
Alternatively, the N—C ₂ -C ₄ alkoxyalkyl compound can be easily isolated from such a mixture by a conventional method such as column chromatography.

The method B is characterized in that various substituents other than a hydrogen atom can be introduced as R ¹ before the formation of the uracil ring. In step 1, a compound of formula [XI] can be obtained by reacting a compound of formula [II] with various amines of formula [X] in the presence of an acid catalyst. The acid used is preferably acetic acid or trifluoroacetic acid.

In step 2, a compound of formula [XI] is reacted with an iso (thio) cyanate of formula [IV] or a (thio) carbamic acid ester of formula [V] in the presence of a base to give The compound of the present invention of formula [IX] can be obtained without isolation of the intermediate of [XII]. Conditions such as base, solvent and reaction temperature used in this step are A
This is almost the same as step 2 of the method.

Method C is an intermediate [VI] in step 2 of Method A.
Is another method of synthesizing. In step 1, the formula [II]
The compound of formula [VI] can be obtained by reacting the compound of formula (X) with (thio) ureas of formula [XIII] in the presence of an acid catalyst in an inert solvent. As the acid catalyst used, strong mineral acids such as sulfuric acid and hydrochloric acid, organic acids such as p-toluenesulfonic acid or phosphoric acids such as orthophosphoric acid and polyphosphoric acid are preferable. As the solvent, benzene, aromatic hydrocarbons such as toluene, carbon tetrachloride, halogenated hydrocarbons such as chlorobenzene or 1,2-dimethoxyethane, 1,
Ethers such as 4-dioxane are preferred. The reaction temperature is
Although any temperature from 20 ° C to the reflux temperature of the reaction mixture can be set, it is preferable to carry out at the reflux temperature.

In step 2, the compound of formula [VI] is cyclized in the presence of a base in an inert solvent to give a compound of formula [VII]
The compound of the present invention can be obtained. The conditions used in this step, such as the base, the solvent, and the reaction temperature, are the same as in step 2 of Method A.
Is almost the same as.

Method D is suitable for the synthesis of the compound of the present invention in which Z ¹ is a sulfur atom. The starting material [XIV] can be synthesized by a known method. In Step 1, as in Step 1 of Method A, the compound of the formula [XIV] can be reacted with ammonia acetate in the presence of acetic acid in an inert solvent such as ethanol to obtain the compound of the formula [XV].

In step 2, the compound of the formula [XV] is reacted with phosgene or thiophosgene in the presence of a base in an inert solvent to obtain the compound of the formula [VII]. The base used is preferably an organic base such as triethylamine or pyridine. As the solvent, aromatic hydrocarbons such as benzene and toluene or halogenated hydrocarbons such as dichloromethane and 1,2-dichloroethane are preferable. The reaction temperature can be set to any temperature from 0 ° C to the reflux temperature of the reaction mixture, but is preferably 0 ° C to 30 ° C. Also, 1,1′-thiocarbonyldiimidazole can be used instead of thiophosgene.

Method E is an intermediate [III] in step 1 of Method A.
] Is another method of synthesizing The compound of the formula [III] can be obtained by reacting the nitrile of the formula [XVI] and the alpha-bromoacetic acid ester of the formula [XVII] in the presence of zinc in an inert solvent. As the solvent used, aromatic hydrocarbons such as benzene and toluene, and ethers such as diethyl ether, tetrahydrofuran, 1,2-dimethoxyethane, and 1,4-dioxane are preferable. The reaction temperature can be set to any temperature from 20 ° C to the reflux temperature of the reaction mixture, but it is preferably carried out at the reflux temperature.

Method F is a method suitable for the case where Z ² is an imino group and the synthesis of the compound of the present invention through which Z ² is an oxygen atom. The starting material of the formula [XVIII] can be synthesized by a known method. The compound of formula [XVIII] and the formula [I
The compound of the formula [XIX] can be obtained by reacting V] or the compound of the formula [V] in the presence of a base in an inert solvent. The conditions of the base, solvent and reaction temperature used in the reaction are almost the same as those in Step 2 of Method A. Then, the compound of the formula [XIX] can be hydrolyzed under acidic conditions to obtain the compound of the present invention of the formula [VII]. The acid used is preferably a mineral acid such as hydrochloric acid, sulfuric acid, nitric acid, etc., and more preferably a diluted aqueous solution thereof. The reaction temperature can be set to any temperature from 20 ° C to the reflux temperature of the reaction mixture, but it is preferably carried out at the reflux temperature.

Method G is a method for converting oxygen atoms of Z ² into sulfur atoms. The compound of formula [XX] can be obtained by reacting the compound of formula [IX] with phosphorus pentasulfide or Lawesson's reagent in an inert solvent. Examples of the solvent include ethers such as tetrahydrofuran, 1,4-dioxane, and 1,2-dimethoxyethane, aromatic hydrocarbons such as benzene and toluene, dimethylformamide, dimethylsulfoxide, and hexamethylphosphoric triamide. The reaction temperature can be set to any temperature from 20 ° C. to the reflux temperature of the reaction mixture, but it is preferably carried out at the reflux temperature.

Method H is a method of converting the hydrogen atom of the uracil derivative of the formula [XXI] in which R ² is a hydrogen atom into a halogen atom, a nitro group or a thiocyanate group to obtain the compound of the present invention of the formula [XXII]. As the halogenating agent, chlorination is chlorine, sulfuryl chloride or N-chlorosuccinimide, and bromination is bromine, sulfuryl bromide or N-.
It is preferable to use bromosuccinimide and iodine or iodine monochloride for iodination. As the solvent, acetic acid or a halogenated hydrocarbon such as dichloromethane or carbon tetrachloride is preferably used. The reaction temperature can be set to any temperature from 0 ° C to the reflux temperature of the reaction mixture, but it is preferably carried out in the range from 20 ° C to the reflux temperature.

As the nitrating agent, nitric acid or a mixture of nitric acid and sulfuric acid is preferably used. As the solvent, halogenated hydrocarbons such as dichloromethane and 1,2-dichloroethane or acetic acid are preferable, but the solvent may not be used. The reaction temperature can be set to any temperature from 0 ° C to the reflux temperature of the reaction mixture, but is preferably 0 ° C to 50 ° C. As the thiocyanating agent, it is preferable to generate thiocyanogen using ammonium thiocyanate and bromine. As the solvent, it is preferable to use halogenated hydrocarbons such as dichloromethane and carbon tetrachloride, ethers such as 1,2-dimethoxyethane and tetrahydrofuran, or acetic acid. The reaction temperature can be set to any temperature from 0 ° C to 50 ° C, but is preferably 0 ° C to 30 ° C.

Method I is a method of converting the halogen atom at the 5-position into a cyano group. Compound of formula [XXIII] and formula [XXIV]
The compound of formula [XXV] can be obtained by reacting the cyan compound of ## STR3 ## in an inert solvent. As the solvent, alcohols such as methanol and ethanol, tetrahydrofuran, ethers such as 1,2-dimethoxyethane, aromatic hydrocarbons such as benzene and toluene, dimethylformamide, N-methylpyrrolidone, dimethyl sulfoxide, hexamethylphosphoric Triamide etc. are mentioned. The reaction temperature can be set to any temperature from 20 ° C to the reflux temperature of the reaction mixture, but it is preferably carried out at 100 ° C to the reflux temperature.

In each production method (method A to method I), the molar ratio of each reactant is not particularly limited, but it is advantageous to carry out the reaction in an equimolar ratio or a ratio close thereto. When the compound of the present invention needs to be purified, it can be separated and purified by any purification method such as recrystallization, column chromatography and thin layer chromatography.

Among the compounds included in the present invention, the compounds having an asymmetric carbon atom include the optically active compounds (+) and (−). Further, when the configurational isomers are present, cis isomers and trans isomers are included.

In using the compound of the present invention as a pest controlling agent, generally, a suitable carrier, for example, solid carrier such as clay, talc, bentonite, diatomaceous earth or the like, alcohols such as water, methanol and ethanol, benzene, toluene, Aromatic hydrocarbons such as xylene, chlorinated hydrocarbons, ethers, ketones, esters such as ethyl acetate, and acid amides such as dimethylformamide can be mixed and applied, if desired. By adding an emulsifier, a dispersant, a suspending agent, a penetrating agent, a spreading agent, a stabilizer, etc., it can be put into practical use as an arbitrary formulation such as emulsion, oil, wettable powder, granule, flowable agent. .

If desired, it may be mixed with other herbicides, various insecticides, fungicides, plant growth regulators, synergists and the like during formulation or spraying. The application dose of the compound of the present invention varies depending on the application scene, application time, application method, target pests, cultivated crops, etc., but in general, about 0.005 to 50 kg per hectare of the active ingredient is suitable.

Next, the compounding ratios and types of various preparations of the present invention will be described below.

[0046]

[Table 1] ──────────────────────────────────                 Active ingredient Carrier Surfactant Other ingredients (adjuvant) ──────────────────────────────────   Emulsion 1 to 25 52 to 95 3 to 20 0 to 20   Oil 1-30 57-99   Flowable agent 1-70 10-90 1-200-10   Hydrating agent 1-70 15-93 3-10 0-5   Powder 0.01 to 30 67 to 99.5 0 to 3   Granules 0.01 to 30 67 to 99.5 0 to 8 ──────────────────────────────────   Numerical values in the above table indicate% by weight.

In application, emulsions, oils, flowables and wettable powders are diluted with a predetermined amount of water and then sprayed, while powders and granules are directly sprayed without being diluted with water.

Next, examples of each component in each of the above-mentioned preparations will be given. Emulsion Active ingredient: Compound of the present invention Carrier: Xylene, dimethylformamide, methylnaphthalene, cyclohexanone, dichlorobenzene,
Isophorone surfactant: Sorpol 2680, Sorpol 3005X, Sorpol 3353 Other components: Piperonyl butoxide, benzotriazole oil Active ingredient: Compound of the present invention: Xylene, methylcellosolve, Kerosene flowable agent Active ingredient: Compound of the present invention Body: Water surfactant: Lunox 1000C, Solpol 3353, Soprofer FL, Nipol, Aglycol S-710, Sodium lignin sulfonate Other ingredients: Zansan gum, formalin, ethylene glycol, propylene glycol wettable powder Active ingredient: Compound of the present invention Carrier: Calcium carbonate, kaolinite, Sieglite D, Sieglite PFP, diatomaceous earth, talc Surfactant: Solpol 5039, Lunox 1000C, calcium lignin sulfonate, sodium dodecylbenzene sulfonate, Solpol 5050, Lepore 005D, Sorpol 5029-0 Other ingredient: Carplex # 80 Dusts active ingredient: Present compound responsible body: calcium carbonate, kaolinite, Zeeklite D, talc Other ingredients: diisopropyl phosphate, Carplex # 80 Granules ( 1) Active ingredient: Compound of the present invention carrier: Calcium carbonate, kaolinite, bentonite, talc Other components: Calcium lignin sulfonate, polyvinyl alcohol granules (2) [Bait agent] Active ingredient: Compound carrier of the present invention: Flour, bran, corn grit, siegrite D Other ingredients: paraffin, soybean oil

[0049]

EXAMPLES Examples (Synthesis Examples, Formulation Examples, Test Examples) Hereinafter, the present invention will be specifically described with reference to Examples (Synthesis Examples, Formulation Examples, Test Examples).

[Synthesis Example] The compounds included in the present invention are
Although prepared or could be prepared based on the synthetic examples shown below, the present invention is not limited to these compounds.

Synthesis Example 1 3- (4-trifluoromethylthiophenyl) -6-
(2,6-difluorophenyl) -2,4 (1H, 3
H) -pyrimidinedione (inventive compound No. 1.82) sodium hydride (purity 55
%) 0.15 g was added to 30 mL of 1,4-dioxane, and ethyl 3-amino-3- (2,6-difluorophenyl) -2-propenoate 0.70 g of 1,4-dioxane was added with stirring under ice cooling. 10 mL of the solution was added dropwise. After stirring for 15 minutes at room temperature, 0.8 g of ethyl 4-trifluoromethylthiophenyl carbamate was added. After stirring under reflux for 2 hours, the solvent was distilled off under reduced pressure. The residue was dissolved in 100 mL of water, washed with diethyl ether, and then added to a mixed solution of 50 g of ice and 20 mL of concentrated hydrochloric acid. After extraction with 100 mL of ethyl acetate, washing with saturated saline,
After drying over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure to obtain 0.18 g of a crude product. The crystals were washed with diisopropyl ether to obtain 0.15 g of the desired compound.

Melting point: 258.0-261.0 ° C. ¹ H-NMR (CDCl ₃ + CD ₃ OD, TMS, δppm): 5.99 (1 H, s), 6.90
~ 7.95 (7H, m).

Synthesis Example 2 3- (difluoro-3,4-dioxymethylenephenyl) -6- (2,6-difluorophenyl) -2,4
(1H, 3H) -Pyrimidinedione (inventive compound No. 1.28) sodium hydride (purity 55
%) 0.4 g was added to 20 mL of dimethylformamide, and 10 mL of a dimethylformamide solution of 2.3 g of ethyl 3-amino-3- (2,6-difluorophenyl) -2-propenoate was added dropwise with stirring under ice-cooling. After stirring at room temperature for 15 minutes, the mixture was cooled to -60 ° C, and then 2.0 g of difluoro-3,4-dioxymethylenephenylisocyanate was added dropwise.
After gradually warming to room temperature, the mixture was further stirred for 3 hours. After evaporating the solvent under reduced pressure, 100 mL of water was added to dissolve the residue, and the mixture was washed with diethyl ether. The aqueous layer was added to a mixed solution of 50 g of ice and 20 mL of concentrated hydrochloric acid, and then 100 mL of ethyl acetate was added for extraction.
The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to give a crude product. The crystals were washed with diisopropyl ether to give the desired compound.
Obtained 0.9 g.

Melting point: 243.0-244.0 ° C. ¹ H-NMR (CDCl ₃ + DMSO d-6, TMS, δ ppm): 5.89 (1 H, s),
7.00 ~ 7.90 (6H, m), 11.82 (1H, s).

Synthesis Example 3 3- {4- (3-chloro-5-trifluoromethyl-2)
-Pyridyloxy) phenyl} -6- (2,6-difluorophenyl) -2,4 (1H, 3H) -pyrimidinedione (inventive compound No. 1.55) Synthesized according to Synthesis Example 2 3
3.8 g of-(4-methoxyphenyl) -6- (2,6-difluorophenyl) -2,4 (1H, 3H) -pyrimidinedione was added to 200 mL of dry dichloromethane, and -60 ° C.
With stirring at 2.18 mL of boron tribromide was added. After warming to room temperature, the mixture was further stirred at room temperature for 12 hours. Reaction mixture with ice water
In 200 mL, the dichloromethane layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to give 3- (4-hydroxyphenyl) -6- (2,6-difluorophenyl) -2,4 ( 2.1 g of 1H, 3H) -pyrimidinedione
Obtained.

0.15 g of sodium hydride (purity 55%) was added to 20 mL of dimethylformamide, and the mixture of 3- (4-hydroxyphenyl) -6-obtained above was stirred under ice cooling.
(2,6-difluorophenyl) -2,4 (1H, 3
H) -Pyrimidinedione 0.9 g was added. After stirring at room temperature for 15 minutes, 0.7 g of 2,3-dichloro-5-trifluoromethylpyridine was added, and the mixture was stirred at 80 ° C for 2 hours. After the solvent was distilled off under reduced pressure, 100 mL of ethyl acetate was added to dissolve it, and 100 m of water was added.
Washed with L. After drying over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure to obtain a crude product. The crystals were washed with diisopropyl ether to obtain 0.9 g of the target compound.

Melting point: 221.0-222.0 ° C. ¹ H-NMR (CDCl ₃ + DMSO d-6, TMS, δ ppm): 5.86 (1 H, s),
7.00 ~ 7.90 (7H, m), 8.39 (1H, s), 8.54 (1H, s).

Synthesis Example 4 3- (4-trifluoromethylphenyl) -5-iodo-6- (2-fluorophenyl) -2,4 (1H, 3
H) -pyrimidinedione (inventive compound No. 1.29) 3 synthesized according to Synthesis Example 2
0.25 g of-(4-trifluoromethylphenyl) -6- (2-fluorophenyl) -2,4 (1H, 3H) -pyrimidinedione was added to 50 mL of dichloromethane, and 0.14 g of iodine monochloride with stirring under ice cooling. Was dripped. After stirring at room temperature for 3 hours, an aqueous solution of sodium thiosulfate was added, and then 50 mL of chloroform was added for extraction. The organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to give a crude product. The crystals were washed with diisopropyl ether to obtain 0.13 g of the desired compound.

Melting point: 235.0-236.0 ° C. ¹ H-NMR (CDCl ₃ + DMSO d-6, TMS, δppm): 7.05 to 8.00 (8
H, m), 12.05 (1H, bs).

Synthesis Example 5 3- (3,4-dichlorophenyl) -5-bromo-6-
(4-Fluorophenyl) -2,4 (1H, 3H) -pyrimidinedione (Compound of the present invention No. 1.14) 3 synthesized according to Synthesis Example 2
-(3,4-Dichlorophenyl) -6- (4-fluorophenyl) -2,4 (1H, 3H) -pyrimidinedione
0.5 g was added to 10 mL of acetic acid, and bromine was added with stirring under ice cooling.
5 mL was added dropwise. After stirring at room temperature for 2 hours, 100 mL of ice water was added, and the precipitated crystals were collected by filtration. The crystals were dried and washed with diisopropyl ether to give the desired compound.
3g was obtained.

Melting point: 277.0-279.0 ° C. ¹ H-NMR (CDCl ₃ + DMSO d-6, TMS, δppm): 7.10 to 7.90 (7
H, m).

Synthesis Example 6 3- (3,4-dichlorophenyl) -6- (2,6-difluorophenyl)-(1H, 3H) -pyrimidine-2
-Thion-4-one (Compound of the present invention No. 1.31) Sodium hydride (Purity 55
%) 0.4 g was added to 50 mL of dimethylformamide, and 10 mL of a dimethylformamide solution of 2.3 g of ethyl 3-amino-3- (2,6-difluorophenyl) -2-propenoate was added dropwise with stirring under ice-cooling. After stirring at room temperature for 15 minutes, the mixture was cooled to -60 ° C, and 10 mL of a dimethylformamide solution containing 2.1 g of 3,4-dichlorophenylisothiocyanate was added dropwise. After warming to room temperature, the mixture was further stirred for 3 hours. The solvent was distilled off under reduced pressure, 100 mL of water and 100 mL of ether were added and well stirred, and the generated insoluble matter was filtered off. The aqueous layer was poured into cold 5% hydrochloric acid water, and the precipitated crystals were collected by filtration. The crystals were dried and washed with diisopropyl ether to obtain 0.8 g of the target compound.

Melting point: 250.0-252.0 ° C. ¹ H-NMR (CDCl ₃ + DMSO d-6, TMS, δ ppm): 6.18 (1 H, s),
7.00 ~ 7.85 (6H, m), 13.18 (1H, bs).

Synthesis Example 7 3- (4-trifluoromethoxyphenyl) -6-
(2,6-Difluorophenyl)-(1H, 3H) -pyrimidin-2-one-4-thione (Compound of the present invention No. 1.17) 3 synthesized according to Synthesis Example 2
-(4-trifluoromethoxyphenyl) -6- (2,
1.0-g of 6-difluorophenyl) -2,4 (1H, 3H) -pyrimidinedione and Lawesson's reagent [2,4-bis (4-methoxyphenyl) -1,3-dithia-2,4-
2.0 g of diphosphetane-2,4-disulfide] was added to 30 mL of 1,4-dioxane, and the mixture was stirred under reflux for 6 hours. After evaporating the solvent under reduced pressure, the residue was purified by preparative thin layer chromatography using a mixed solvent of chloroform and ethyl acetate as a developing solvent to obtain 0.4 g of the target compound.

Melting point: 240.0-241.0 ° C. ¹ H-NMR (CDCl ₃ + DMSO d-6, TMS, δ ppm): 6.70 (1 H, s),
7.00 ~ 7.80 (7H, m), 12.30 (1H, bs).

Synthesis Example 8 3- (4-trifluoromethoxyphenyl) -6- (2
-Chlorophenyl) -2,4 (1H, 3H) -pyrimidinedione (inventive compound No. 1.20) 3 synthesized according to Synthesis Example 6
-(4-trifluoromethoxyphenyl) -6- (2-
Chlorophenyl)-(1H, 3H) -pyrimidine-2-
Thion-4-one (0.9 g) and Lawesson's reagent (1.8 g) were added to 20 mL of hexamethylphosphoric triamide (20 mL), and the mixture was stirred at 120 ° C for 2 hours. After the solvent was distilled off under reduced pressure, chloroform was used as an eluent and silica gel column chromatography was performed to obtain 0.1 g of the target compound.

Melting point: 255.0-257.0 ° C. ¹ H-NMR (CDCl ₃ + DMSO d-6, TMS, δ ppm): 6.07 (1 H, s),
7.30 ~ 7.60 (7H, m), 13.04 (1H, s).

Synthetic Example 9 Hydrogenation of 3- (4-trifluoromethoxyphenyl) -4-imino-5-cyano-6-phenyl- (1H, 3H) -pyrimidin-2-one (invention compound No. 1.47) Sodium (purity 55
%) 0.23 g was added to 10 mL of dimethylformamide, and 0.85 g of 2-cyano-3-amino-3-phenylacrylonitrile was added with stirring under ice cooling. After stirring at room temperature for 15 minutes, the mixture was cooled to -30 ° C, and then 1.02 g of 4-trifluoromethoxyphenyl isocyanate was added dropwise. The mixture was gradually warmed to room temperature, stirred for another 3 hours, and then the solvent was distilled off under reduced pressure. The residue was dissolved in 100 mL of water, washed with ethyl ether, and the aqueous layer was neutralized with cooled dilute hydrochloric acid until the pH reached 7. The precipitated crystals were collected by filtration and dried,
0.58 g of the target compound by washing with diisopropyl ether
Obtained.

Melting point: 252.0-256.0 ° C. ¹ H-NMR (CDCl ₃ + DMSO d-6, TMS, δppm): 7.25 to 7.98 (8
H, m).

Synthesis Example 10 1-Amino-3- (4-trifluoromethoxyphenyl) -6- (2-chlorophenyl) -2,4 (1H, 3
H) -pyrimidinedione (inventive compound No. 1.118) 3- (4-trifluoromethoxyphenyl) -6- (2 synthesized according to Synthesis Example 2
-Chlorophenyl) -2,4 (1H, 3H) -pyrimidinedione 0.8 g and 2,4-dinitrophenoxyamine
0.5 g was added to 20 mL of dimethylformamide, and 0.4 g of potassium carbonate was added with stirring at room temperature. After stirring at room temperature for 3 days, 0.2 g of potassium carbonate was added, and the mixture was further stirred for 2 hours. After the solvent was distilled off under reduced pressure, 100 mL of ethyl acetate was added and dissolved. This was washed twice with a 2% aqueous sodium hydroxide solution, further washed with water, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain 0.6 g of a crude product. This was purified by preparative thin layer chromatography using a mixed solvent of chloroform and ethyl acetate as a developing solvent to obtain 0.4 g of the target compound.

Melting point: 245.0-246.0 ° C. ¹ H-NMR (CDCl ₃ + DMSO d-6, TMS, δppm): 5.14 (2H, bs),
5.70 (1H, s), 7.50 (8H, bs).

The compounds shown in Tables 2 and 3 were synthesized or could be synthesized according to the above synthesis examples. Second
Q1 to Q61 in Tables and Table 3 are groups represented by the following formula.

[0073]

[Chemical 17]

[0074]

[Chemical 18]

[0075]

[Chemical 19]

[0076]

[Chemical 20]

Table 2

[0078]

[Chemical 21]

[0079]

[Table 2] ─────────────────────────────────── No. R ¹ R ² X _l Y _m Z ¹ Z ² Melting point (℃) ─────────────────────────────────── 1.1 HH 2,6-F ₂ 3-Cl-4-OCF ₃ OO 208.0-209.0 1.2 HH 2-Cl 4-CH ₂ C ₆ H ₅ OO 218.0-219.0 1.3 HI 2-Cl 4-CF ₃ OO 261.0-263.0 1.4 HI 2-Cl-6 -F 4-CF ₃ OO 259.0-260.0 1.5 HH 2,6-F ₂ 3-Cl-4-OCF ₂ CHF ₂ OO 234.0-235.0 1.6 HH 2-Cl 3-Cl-4-CN OO 240.0-241.0 1.7 HH 2-Cl 3-CN-4-Cl OO 247.0-248.0 1.8 HH 4-F 4-OCF ₃ OO 247.0-249.0 1.9 HH 4-F 4-CF ₃ OO 293.0-295.0 1.10 HH 4-F 3,4-Cl ₂ OO> 300.0 1.11 H Cl 4-F 4-OCF ₃ OO 234.0-236.0 1.12 HI 4-F 4-CF ₃ OO 251.0-253.0 1.13 H Cl 4-F 3,4-Cl ₂ OO 188.0-189.0 1.14 H Br 4-F 3,4-Cl ₂ OO 277.0-279.0 1.15 HH 2-Cl 3-CH ₃ -4-Br OO 241.0-242.0 ───────────────────── ───────────────

[0080]

[Table 3] ─────────────────────────────────── No. R ¹ R ² X _l Y _m Z ¹ Z ² Melting point (℃) ─────────────────────────────────── 1.16 HH 2,6-F ₂ 3-CH ₃ -4-Br OO 219.0-220.0 1.17 HH 2,6-F ₂ 4-OCF ₃ OS 240.0-241.0 1.18 HH 4-F 4-OCF ₃ OO 185.0-186.0 1.19 HH 4-F 4-OCF ₃ OO 160.0-161.0 1.20 HH 2-Cl 4-OCF ₃ SS 255.0-257.0 1.21 HH 2,6-F ₂ 3-OCH ₃ -4-OCF ₃ OO 145.0-146.0 1.22 HH 2,6-F ₂ 3,4 -F ₂ OO 286.0-289.0 1.23 HH 2,6-F ₂ 3-F-4-CH ₃ OO 222.0-224.0 1.24 HH 2-Cl 3,4-Cl ₂ SO 243.0-244.0 1.25 HH 2-Cl 4-CF ₃ SO 259.0-260.0 1.26 HH 2,6-F ₂ 4-CF ₃ SO 256.0-257.0 1.27 HH 2-Cl 3-OCF ₂ O-4 OO 270.0-271.0 1.28 HH 2,6-F ₂ 3-OCF ₂ O -4 OO 243.0-244.0 1 29 HI 2-F 4-CF ₃ OO 235.0-236.0 1.30 HI 2,6-F ₂ 4-CF ₃ OO 239.0-240.0 1.31 HH 2,6-F ₂ 3,4-Cl ₂ SO 250.0-252.0 1.32 HH 2,6-F ₂ 4-Cl OS 242.0-243.0 1.33 HH 2-F 4-CF ₃ OS 276.0-278.0 1.34 HH 2,6-F ₂ 4-CF ₃ OS 235.0-236.0 1.3 5 HH 2-F 4-OCF ₃ OS 248.0-249.0 1.36 HH 2-Cl 3,4-Cl ₂ OS 265.0-266.0 1.37 HH 2-Cl 3-CF ₃ -4-Br OO 235.0-236.0 1.38 HH 2,6 -F ₂ 3-CF ₃ -4-Br OO 227.0-228.0 ────────────────────────────────────

[0081]

[Table 4] ─────────────────────────────────── No. R ¹ R ² X _l Y _m Z ¹ Z ² Melting point (℃) ─────────────────────────────────── 1.39 HH 2,6-F ₂ 4-IOO 269.0-272.0 1.40 HH 2,6-F ₂ 4-NO ₂ OO 300.0-305.0 1.41 HH 2,6-F ₂ 2,4-Cl ₂ OO 221.0-222.0 1.42 HH 2-F 2,4- Cl ₂ OO 201.5-203.0 1.43 HH 2-F 2,3,4-F ₃ OO 255.0-258.0 1.44 HH 2,6-Cl ₂ 4-FOO 255.0-257.5 1.45 HH 2,6-Cl ₂ 4-CF ₃ OO > 300.0 1.46 HH 2,6-Cl ₂ 3,4-Cl ₂ OO 266.0-269.0 1.47 H CN H 4-OCF ₃ O NH 252.0-256.0 1.48 HH 2-Cl 3-Cl-4-IOO 122.0-124.0 1.49 HH 2-Cl 3-Cl-4-OCH ₃ OO 245.0-246.0 1.50 HH 2,6-F ₂ 3-Cl-4-FOO 255.0-256.0 1.51 HH 2,6-F ₂ 3-CF ₃ -4-Cl OO 225.0-227.0 1.52 HH 2,6-F ₂ 3-Cl-4-OCH ₃ OO 239.0-240.0 1.53 HH 2,6-F ₂ 4-OCH ₃ OO 205.0-206.0 1.54 HH 2,6-F ₂ 4-OH OO> 300.0 1.55 HH 2,6-F ₂ 4-O (Q38-3-Cl-5-CF ₃ ) OO 221.0-222.0 1.56 HH 2,6-F ₂ 4-O (C ₆ H ₃ -2-Cl -4-CF ₃ ) OO 232.0-234.0 1.57 HH 2-Cl 3-CF ₃ OO 249.5-251.0 1.58 HH 2,6-F ₂ 3-CF ₃ OO 216.0-217.5 1.59 HH 2-Cl 3-CH ₃ OO 193.5-195.0 1.60 HH 2,6-F ₂ 3-CH ₃ OO 210.0-212.0 1.61 HH 2-Cl 3-OCH ₃ OO 211.5-212.5 ────────────────────────────────────

[0082]

[Table 5] ─────────────────────────────────── No. R ¹ R ² X _l Y _m Z ¹ Z ² Melting point (℃) ─────────────────────────────────── 1.62 HH 2-F 4- CN OO 273.0-275.0 1.63 HH 2,6-F ₂ 4-CN OO 266.0-267.0 1.64 HH 2,6-F ₂ 4-OCH ₂ CH ₃ OO 255.0-257.0 1.65 HH 2,6-F ₂ 4-O ( Q38-5-Br) OO 221.0-225.0 1.66 HH 2,6-F ₂ 3-Cl-4-CH ₃ OO 216.0-218.0 1.67 HH 2,6-F ₂ 4-COC ₆ H ₅ OO 263.0-265.0 1.68 HH 2,6-F ₂ 3-Cl-4-IOO 225.0-229.0 1.69 HH 2,6-F ₂ 4-CF ₂ CF ₃ OO 257.0-259.5 1.70 HH 2,6-F ₂ 2,3-Cl ₂ OO 139.5 -143.0 1.71 HH 2,6-F ₂ 2,5-Cl ₂ OO 228.0-231.5 1.72 HH 2,6-F ₂ 3,5-Cl ₂ OO 264.0-266.0 1.73 HH 2-Cl 2,3-Cl ₂ OO 229.0-232.0 1.74 HH 2-Cl 3,5-Cl ₂ OO 291.0-296.0 1.75 HH 2,6-Cl ₂ 2-F-4-Cl OO 269.5-275.0 1.76 HH 2-Br 4-Cl OO 274.0-277.5 1.77 HH 2-Br 2-F-4-Cl OO 225.0-226.5 1.78 HH 2-Br 3,4-Cl ₂ OO 245.0-248.5 1.79 HH 2-CH ₃ 4-Cl OO 240.0-241.5 1.80 HH 2-CH ₃ 4 -CF ₃ OO 256.0-2 60.0 1.81 HH 2-CH ₃ 3,4-Cl ₂ OO 231.0-234.0 1.82 HH 2,6-F ₂ 4-SCF ₃ OO 258.0-261.0 1.83 HH 2-OCH ₃ 4-Cl OO 247.0-251.0 1.84 HH 2, 4-Cl ₂ 4-Cl OO 287.0-293.0 ────────────────────────────────────

[0083]

[Table 6] ─────────────────────────────────── No. R ¹ R ² X _l Y _m Z ¹ Z ² Melting point (℃) ─────────────────────────────────── 1.85 HH 2,4-Cl ₂ 3,4-Cl ₂ OO 285.0-288.0 1.86 HH 2-Cl 4-Cl OS 284.0-287.0 1.87 HH 2-Cl 4-Br OS 263.0-267.0 1.88 CH ₃ H 2-Cl 4-Cl OO 254.0-257.0 1.89 HH 2,6-F ₂ 2-F-4-OCH ₃ OO 215.0-216.0 1.90 HH 2,6-F ₂ 2-F-4-OH OO> 300.0 1.91 HH 2,6-F ₂ 2-F-4 -O (C ₆ H ₃ -2-Cl-4-CF ₃ ) OO 202.0-204.0 1.92 HH 2,6-F ₂ 4-OCH ₂ CF ₃ OO 264.0-265.0 1.93 HH 2,6-F ₂ 4-CH ₂ CH ₃ OO 240.0-242.0 1.94 HH 2,6-F ₂ 2-Cl-4-Br OO 222.0-223.0 1.95 HI 2,6-F ₂ 2,3,4-Cl ₃ OO 216.0-217.0 1.96 HI 2, 6-F ₂ 3,4- (CH ₃ ) ₂ OO 235.0-237.0 1.97 HH 2,6-F ₂ 3,4,5-Cl ₃ OO 256.0-257.0 1.98 HH 2-Cl 2-Cl-4-Br OO 242.0-243.0 1.99 HH 2-Cl 2,3,4-Cl ₃ OO 232.0-233.0 1.100 HH 2,6-F ₂ 2,5-F ₂ OO 207.0-209.0 1.101 HH 2,6-F ₂ 2-F- 4-O (Q38-3-Cl-5-CF ₃ ) OO> 300.0 1.102 HH 2,6-F ₂ 2-Cl O O 212.0-216.0 1.103 HH 2,6-F ₂ 3-Cl OO 217.0-219.0 1.104 HH 2,6-F ₂ 2-CF ₃ OO 136.0-141.0 1.105 HH 2-Cl 2-CF ₃ OO 181.0-185.0 1.106 HH 2,6-F ₂ 3-Br OO 211.0-213.0 1.107 HH 2,6-F ₂ 2,3,4,5-Cl ₄ OO 252.0-254.0 ──────────────── ────────────────────

[0084]

[Table 7] ─────────────────────────────────── No. R ¹ R ² X _l Y _m Z ¹ Z ² Melting point (℃) ─────────────────────────────────── 1.108 HH 2,6-F ₂ 4-OCI = CF ₂ OO 217.0-220.0 1.109 HH 2-Cl-4-F 4-OCF ₃ OO 249.5-251.0 1.110 HH 2-Cl-4-F 4-CF ₃ OO 262.5-264.0 1.111 HH 2-Cl -4-F 3,4-Cl ₂ OO 270.0-272.0 1.112 HH 2-Br 4-FOO 257.5-260.0 1.113 HH 2-Br 4-CH ₃ OO 251.0-253.0 1.114 HH 2-Br 4-CF ₃ OO 264.0- 265.0 1.115 HH 2,4-F ₂ 4-OCF ₃ OO 231.0-232.0 1.116 HH 2,4-F ₂ 4-CF ₃ OO 239.0-242.0 1.117 HH 2,4-F ₂ 3,4-Cl ₂ OO 257.0- 260.0 1.118 NH ₂ H 2-Cl 4-OCF ₃ OO 245.0-246.0 1.119 HH 2-Cl 2-Cl-4-CF ₃ OO 234.0-235.0 1.120 HH 2-Cl 3-OCF ₃ OO 192.0-194.0 1.121 HH 2, 6-F ₂ 3-OCH ₃ OO 183.0-184.0 1.122 HH 2,6-F ₂ 3-OH OO 277.5-280.0 1.123 HH 2,6-F ₂ 3-O (Q38-3-Cl-5-CF ₃ ) OO 1.124 HH 2,6-F ₂ 3-OCF ₂ CHF ₂ OO 1.125 HH 2,6-F ₂ 3-Cl-4-CF ₃ OO 1.126 HH 2,6-F ₂ 3,5-Cl ₂ -4- CF ₃ OO 1.1 27 HH 2-Cl 3,5-Cl ₂ -4-OCF ₃ OO 1.128 HH 2,6-F ₂ 3,5-Cl ₂ -4-OCF ₃ OO 1.129 HH 2,4,6-F ₃ 4-Cl OO 1.130 HH 2,4,6-F ₃ 3,4-Cl ₂ OO ───────────────────────────────── ───

[0085]

[Table 8] ─────────────────────────────────── No. R ¹ R ² X _l Y _m Z ¹ Z ² Melting point (℃) ─────────────────────────────────── 1.131 H H 2,4,6-F ₃ 4-OCF ₃ OO 1.132 SC ₆ H ₅ H 2,6-F ₂ 4-OCF ₃ OO 1.133 S (C ₆ H ₄ -2-CH ₃ ) H 2,6-F ₂ 4-Cl OO 1.134 S (C ₆ H ₄ -3-CH ₃ ) H 2,6-F ₂ 3,4-Cl ₂ OO 1.135 S (C ₆ H ₄ -4-CH ₃ ) H 2-Cl 4 -OCF ₃ OO 1.136 S (C ₆ H ₄ -4-Cl) H 2-Cl 4-CF ₃ OO 1.137 S (C ₆ H ₄ -4-Br) H 2,6-F ₂ 4-OCF ₃ OO 1.138 S (C ₆ H ₄ -2-CH (CH ₃ ) ₂ ) H 2,6-F ₂ 4-Cl OO 1.139 S (C ₆ H ₄ -4-C (CH ₃ ) ₃ ) H 2,6-F ₂ 3,4-Cl ₂ OO 1.140 S (C ₆ H ₄ -2-NO ₂ ) H 2-Cl 4-OCF ₃ OO 1.141 S (C ₆ H ₄ -2-CO ₂ CH ₃ ) H 2-Cl 4 -CF ₃ OO 1.142 S (C ₆ H ₄ -2-CO ₂ CH ₂ CH ₃ ) H 2,6-F ₂ 4-OCF ₃ OO 1.143 S (C ₆ H ₄ -2,4- (NO ₂ ) ₂ ) H 2,6-F ₂ 4-Cl OO 1.144 SCCl ₃ H 2,6-F ₂ 3,4-Cl ₂ OO 1.145 SCO ₂ CH ₂ CH ₂ CH ₃ H 2-Cl 4-OCF ₃ OO 1.146 SN ( CH ₃ ) CH ₂ CH ₂ CH ₂ CH ₃ H 2-Cl 4-CF ₃ OO 1.147 SN (CH ₂ CH ₂ CH ₂ CH ₃ ) ₂ H 2,6-F ₂ 4-OCF ₃ OO 1.148 SN (CH ₃ ) CO ₂ CH (CH ₃ ) ₂ H 2,6-F ₂ 4-Cl OO 1.149 SN (CH ₃ ) CO ₂ CH ₂ CH ₂ CH ₃ H 2,6-F ₂ 3,4-Cl ₂ OO 1.150 SN (CH ₂ CH ₃ ) C0 ₂ CH ₃ H 2-Cl 4-OCF ₃ OO 1.151 SN (CH (CH ₃ ) ₂ ) CO ₂ CH ₃ H 2-Cl 4-CF ₃ OO 1.152 SN (CH ₂ CH ₂ CH ₃ ) C O ₂ CH ₃ H 2,6-F ₂ 4-OCF ₃ OO 1.153 SN (CH ₃ ) CH ₂ CH ₂ CO ₂ CH ₃ H 2,6-F ₂ 4-Cl OO ────────── ──────────────────────────

[0086]

[Table 9] ─────────────────────────────────── No. R ¹ R ² X _l Y _m Z ¹ Z ² Melting point (℃) ─────────────────────────────────── 1.154 NH ₂ H 2-Cl 4-CF ₃ OO 1.155 NH ₂ H 2-Cl 3,4-Cl ₂ OO 1.156 NH ₂ H 2-Cl 4-Cl OO 1.157 NH ₂ H 2-Cl 4-CH ₃ OO 1.158 NH ₂ H 2-Cl 4 -Br OO 1.159 NH ₂ H 2-Cl 4-OCF ₃ OS 1.160 NH ₂ H 2-F 4-OCF ₃ OO 1.161 NH ₂ H 2-F 4-OCF ₂ CHF ₂ OO 1.162 NH ₂ H 2-F 2- F-4-Cl OO 1.163 NH ₂ H 2,6-F ₂ 2-Cl-4-CF ₃ OO 1.164 NH ₂ H 2,6-F ₂ 4-Cl OO 1.165 NH ₂ H 2,6-F ₂ 4 -Br OO 1.166 NH ₂ H 2,6-F ₂ 4-CF ₃ OO 1.167 NH ₂ H 2,6-F ₂ 4-OCF ₃ OO 1.168 NH ₂ H 2,6-F ₂ 2-F-4-Cl OO 1.169 NH ₂ H 2,6-F ₂ 3,4-Cl ₂ OO 1.170 NH ₂ H 2,6-F ₂ 4-OCF ₃ SO 1.171 NH ₂ H 2,6-F ₂ 4-OCF ₃ OS 1.172 NH ₂ H 2-Br 4-OCF ₃ OO 1.173 NH ₂ H 2,4-F ₂ 4-OCF ₃ OO 1.174 NH ₂ H 2-Cl-6-F 4-Cl OO 1.175 NH ₂ H 2-Cl-4- F 4-OCF ₃ OO 1.176 CN H 2-Cl 4-CF ₃ OO ───────────── ──────────────────────

[0087]

[Table 10] ─────────────────────────────────── No. R ¹ R ² X _l Y _m Z ¹ Z ² Melting point (℃) ─────────────────────────────────── 1.177 CN H 2-Cl 3 , 4-Cl ₂ OO 1.178 CN H 2-Cl 4-Cl OO 1.179 CN H 2-Cl 4-CH ₃ OO 1.180 CN H 2-Cl 4-Br OO 1.181 CN H 2-Cl 4-OCF ₃ OS 1.182 CN H 2-F 4-OCF ₃ OO 1.183 CN H 2-F 4-OCF ₂ CHF ₂ OO 1.184 CN H 2-F 2-F-4-Cl OO 1.185 CN H 2,6-F ₂ 2-Cl-4 -CF ₃ OO 1.186 CN H 2,6-F ₂ 4-Cl OO 1.187 CN H 2,6-F ₂ 4-Br OO 1.188 CN H 2,6-F ₂ 4-CF ₃ OO 1.189 CN H 2,6 -F ₂ 4-OCF ₃ OO 1.190 CN H 2,6-F ₂ 2-F-4-Cl OO 1.191 CN H 2,6-F ₂ 3,4-Cl ₂ OO 1.192 CN H 2,6-F ₂ 4-OCF ₃ SO 1.193 CN H 2,6-F ₂ 4-OCF ₃ OS 1.194 CN H 2-Br 4-OCF ₃ OO 1.195 CN H 2,4-F ₂ 4-OCF ₃ OO 1.196 CN H 2-Cl -6-F 4-Cl OO 1.197 CN H 2-Cl-4-F 4-OCF ₃ OO ──────────────────────────── ────────

[0088]

[Table 11] ─────────────────────────────────── No. R ¹ R ² X _l Y _m Z ¹ Z ² Melting point (℃) ─────────────────────────────────── 1.198 COCO ₂ CH ₃ H 2 -Cl 4-CF ₃ OO 1.199 COCO ₂ CH ₂ CH ₃ H 2-Cl 3,4-Cl ₂ OO 1.200 COCO ₂ CH ₃ H 2-Cl 4-Cl OO 1.201 COCO ₂ CH ₂ CH ₃ H 2-Cl 4 -CH ₃ OO 1.202 COCO ₂ CH ₃ H 2-Cl 4-Br OO 1.203 COCO ₂ CH ₂ CH ₃ H 2-Cl 4-OCF ₃ OS 1.204 COCO ₂ CH ₃ H 2-F 4-OCF ₃ OO 1.205 COCO ₂ CH ₂ CH ₃ H 2-F 4-OCF ₂ CHF ₂ OO 1.206 COCO ₂ CH ₃ H 2-F 2-F-4-Cl OO 1.207 COCO ₂ CH ₂ CH ₃ H 2,6-F ₂ 2-Cl- 4-CF ₃ OO 1.208 COCO ₂ CH ₃ H 2,6-F ₂ 4-Cl OO 1.209 COCO ₂ CH ₂ CH ₃ H 2,6-F ₂ 4-Br OO 1.210 COCO ₂ CH ₃ H 2,6-F ₂ 4-CF ₃ OO 1.211 COCO ₂ CH ₂ CH ₃ H 2,6-F ₂ 4-OCF ₃ OO 1.212 COCO ₂ CH ₃ H 2,6-F ₂ 2-F-4-Cl OO 1.213 COCO ₂ CH ₂ CH ₃ H 2,6-F ₂ 3,4-Cl ₂ OO 1.214 COCO ₂ CH ₃ H 2,6-F ₂ 4-OCF ₃ SO 1.215 COCO ₂ CH ₂ CH ₃ H 2,6-F ₂ 4-OCF ₃ OS 1.216 COCO ₂ CH ₃ H 2-Br 4-OCF ₃ OO 1.217 COCO ₂ CH ₂ CH ₃ H 2,4-F ₂ 4-OCF ₃ OO 1.218 COCO ₂ CH ₃ H 2-Cl-6-F 4-Cl OO 1.219 COCO ₂ CH ₂ CH ₃ H 2-Cl-4-F 4-OCF ₃ OO ─────────────────────────────────── ─

Table 3

[0090]

[Chemical formula 22]

[0091]

[Table 12] ─────────────────────────────────── No. R ¹ R ² X _l BZ ¹ Z ² Melting point (℃) ─────────────────────────────────── 2.1 HH 2,6-F ₂ Q38 -6-O (C ₆ H ₃ -2,4-Cl ₂ ) OO 249.0-250.0 2.2 HH 2-Cl Q38-6-O (C ₆ H ₃ -2,4-Cl ₂ ) OO 239.0-240.0 ── ──────────────────────────────────

Formulation Examples Next, formulation examples of the pest control agent containing the compound of the present invention as an active ingredient are shown, but the present invention is not limited thereto. In the following formulation examples,
“Parts” means parts by weight.

Formulation Example 1 Emulsion Compound of the present invention: 5 parts xylene: 70 parts N, N-dimethylformamide ::・ ・ 20 parts Solpol 2680 ・ ・ ・ ・ ・ ・ ・ ・ ・ ・ 5 parts (mixture of non-ionic and anionic surfactants: Toho Chemical Industry Co., Ltd. trade name) To make an emulsion.

In use, the above emulsion was diluted 50 to 20000 times to obtain an amount of active ingredient of 0.005 to 50 kg per hectare.
Sprinkle so that

Formulation Example 2 Wettable powder Compound of the present invention: 25 parts Sikelite PFP: 66 parts (mixture of kaolinite and sericite: Sikhlite Kogyo Co., Ltd. product name) Solpol 5039 ・ ・ ・ ・ ・ ・ ・ ・ ・ ・ 4 parts (anionic surfactant: Toho Chemical Industry Co., Ltd. product name) Carplex # 80・ 3 parts (white carbon: Shionogi Seiyaku Co., Ltd. product name) Calcium lignin sulfonate ・ ・ ・ ・ ・ ・ ・ ・ 2 parts or more are uniformly mixed and pulverized to obtain wettable powder.

When using, the above-mentioned wettable powder is added to 50 to 20000.
Diluted twice and the amount of active ingredient is 0.005 to 50 per hectare
Spread so that it becomes kg.

Formulation Example 3 Oil formulation Compound of the present invention: 10 parts Methyl cellosolve: 90 parts At least 90 parts are uniformly mixed to obtain an oil formulation . At the time of use, the above oil agent is sprinkled so that the amount of the active ingredient is 0.005 to 50 kg per hectare.

Formulation Example 4 Powder Compound of the present invention: 3.0 parts Carplex # 80: 0.5 parts (white carbon: product of Shionogi & Co., Ltd. Name) Clay ・ ・ ・ ・ ・ ・ ・ ・ ・ ・ 95 parts Diisopropyl phosphate ・ ・ ・ ・ ・ ・ ・ ・ ・ ・ 1.5 parts or more are uniformly mixed and pulverized into a powder.

In use, the powder is sprayed so that the amount of active ingredient is 0.005 to 50 kg per hectare.

Formulation Example 5 granules Compound of the present invention ・ ・ ・ ・ ・ ・ ・ ・ ・ ・ 5 parts Bentonite ・ ・ ・ ・ ・ ・ ・ ・ ・ ・ 54 parts Talc ・ ・ ・ ・ ・ ・ ・ ・ ・ ・ 40 parts Lignin Calcium sulfonate: Uniformly mix and crush 1 part or more, add a small amount of water, stir and mix, granulate with an extrusion granulator, and dry to obtain granules. .

In use, the above-mentioned granules are sprinkled so that the amount of the active ingredient is 0.005 to 50 kg per hectare.

Formulation Example 6 Flowable agent Compound of the present invention: 35 parts Solpol 3353: 10 parts (Nonionic surfactant: Toho Chemical Industry Co., Ltd. ) Trade name) Lunox 1000C ・ ・ ・ ・ ・ ・ 0.5 part (Anionic surfactant: Toho Chemical Industry Co., Ltd. trade name) 1% Zansan gum aqueous solution ・ ・ ・ ・ ・ ・ ・ ・ ・ ・ 20 parts (natural) Polymer) Water: 4.5 parts The above components except the active ingredient (the compound of the present invention) are uniformly dissolved, the compound of the present invention is added, and the mixture is stirred well and wet-ground with a sand mill. Get a flowable agent.

When using the above flowable agent,
Diluted 20000 times and the amount of active ingredient is 0.00 per hectare
Sprinkle so that it is 5 to 50 kg.

[Test Example] Next, the usefulness of the compound of the present invention as a pest control agent will be specifically described in the following test examples.

Test Example 1 Insecticidal test against brown planthopper 5% emulsion of the compound of the present invention described in the specification (25% wettable powder depending on the compound was used as a test) was diluted with water containing a spreading agent to give 1000 The drug solution was prepared to have a ppm concentration. 1/2 this chemical
A sufficient amount was applied to the foliage of rice planted in a pot of 0,000 are. After air-drying, a cylinder was set up, 10 second-instar larvae of the brown planthopper were released per pot, capped, and stored in a temperature-controlled room. The survey was conducted after 6 days, and the mortality rate was calculated from the following formula. The test was conducted in a two-division system.

[0106] Mortality rate (%) = (Number of dead insects / Number of released insects) x 100 As a result, the following compounds showed 100% mortality.

Compounds of the present invention: 1.1, 1.3, 1.5, 1.6, 1.7,
1.9, 1.11, 1.12, 1.13, 1.17, 1.19, 1.21, 1.22, 1.
23, 1.25, 1.26, 1.27, 1.28, 1.29, 1.31, 1.32, 1.3
3, 1.34, 1.35, 1.38, 1.39, 1.40, 1.41, 1.42, 1.48,
1.50, 1.51, 1.55, 1.58, 1.59, 1.63, 1.64, 1.65,
1.68, 1.69, 1.70, 1.71, 1.76, 1.77, 1.79, 1.80, 1.
81, 1.82, 1.86, 1.87, 1.89, 1.92, 1.93, 1.94, 1.9
5, 1.96, 1.101.

Test Example 2 Insecticidal test against pearl oyster lady beetle A 5% emulsion of the compound of the present invention described in the specification (25% wettable powder depending on the compound was tested) was diluted with water containing a spreading agent. Then, adjust to a chemical solution of 1000ppm concentration, soak the tomato leaves in this solution for about 10 seconds, air-dry and place in a petri dish.
The head was released and the lid was put on it and stored in a thermostatic chamber at 25 ° C, and the mortality rate after 6 days was calculated from the following formula. The test was conducted in a two-division system.

[0109] Mortality rate (%) = (Number of dead insects / Number of released insects) x 100 As a result, the following compounds showed 100% mortality.

Compounds of the present invention: 1.1, 1.3, 1.4, 1.7, 1.1
1, 1.12, 1.13, 1.17, 1.19, 1.27, 1.28, 1.29, 1.30,
1.34, 1.37, 1.38, 1.39, 1.42, 1.44, 1.45, 1.46,
1.48, 1.50, 1.51, 1.52, 1.55, 1.56, 1.58, 1.68, 1.
69, 1.76, 1.77, 1.78, 1.79, 1.81, 1.82, 1.91, 1.9
5, 1.98, 1.99, 1.101.

Test Example 3 Insecticidal test against Spodoptera litura A 5% emulsion of the compound of the present invention described in the specification (25% wettable powder depending on the compound was tested) was diluted with water containing a spreading agent to give 1000 ppm. Prepare a chemical solution of the concentration, immerse kanlan leaves in this chemical solution for about 10 seconds, air dry and put it in a petri dish, and release 10 second-infested larvae of diamondback moth in 10 petri dishes and cover with a hole. It was stored in a constant temperature chamber at 25 ° C., and the mortality rate after 6 days was calculated from the following formula. The test was conducted in a two-division system.

[0112] Mortality rate (%) = (Number of dead insects / Number of released insects) x 100 As a result, the following compounds showed 100% mortality.

Compounds of the present invention: 1.1, 1.3, 1.5, 1.6, 1.7,
1.8, 1.9, 1.10, 1.11, 1.12, 1.13,1.14, 1.15,1.16,
1.17, 1.18, 1.19, 1.20, 1.21, 1.22, 1.24, 1.25,
1.26,1.27, 1.28,1.29, 1.31, 1.33, 1.34, 1.35, 1.3
6, 1.37, 1.38, 1.39, 1.41,1.43, 1.45,1.49, 1.51,
1.55, 1.56, 1.58, 1.62, 1.68, 1.69, 1.70, 1.72, 1.7
3, 1.74,1.76, 1.77, 1.78, 1.80, 1.82, 1.86, 1.87,
1.91, 1.94, 1.97, 1.98, 1.101.

Test Example 4 Acaricidal Activity Test Against Nymphal Mite A leaf of kidney bean was cut into a circle having a diameter of 3.0 cm using a leaf punch and placed on a wet filter paper on a styrene cup having a diameter of 7 cm. Ten head mite larvae were inoculated into each leaf. A 5% emulsion of the compound of the present invention described in the specification (25% wettable powder depending on the compound was tested) was diluted with water containing a spreading agent to prepare a 1000 ppm concentration solution, and this solution was 2 mL per styrene cup was sprayed using a rotary spraying tower, stored in a thermostatic chamber at 25 ° C., and the mortality rate after 96 hours was calculated from the following formula. The test was conducted in a two-division system.

[0115] Mortality rate (%) = (Number of dead insects / Number of released insects) x 100 As a result, the following compounds showed 100% mortality.

Compounds of the present invention: 1.1, 1.10, 1.11, 1.12,
1.13, 1.14, 1.15, 1.16, 1.18, 1.19,1.24, 1.29,1.3
2, 1.36, 1.48, 1.50, 1.51, 1.52, 1.55, 1.56, 1.58,
1.61,1.63, 1.66,1.68, 1.70, 1.75, 1.78,1.81, 1.8
2, 1.91, 1.94, 1.95, 1.97, 1.101.

Comparative Test Example 3,6-diphenyluracil which is a known compound in the literature (in formula I, X ₁ = hydrogen atom, B = phenyl, R ¹ = hydrogen atom, R ² = hydrogen atom, Z ¹ = oxygen atom, Z ² = oxygen atom) is any pest at 1000 ppm concentration in Test Examples 1 to 4 above.
It did not show any activity against the brown planthopper, the pearl locust, the white-spotted mite, and the spider mite (mortality rate 0%).

[0118]

INDUSTRIAL APPLICABILITY The compound of the present invention has excellent insecticidal and acaricidal activity against many agricultural pests and mites, and has almost no adverse effect on mammals, fish and beneficial insects. Therefore, the compound of the present invention can provide a useful pest control agent.

─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. ⁵ Identification code Internal reference number FI Technical indication location C07D 239/38 7038-4C 239/42 7038-4C 239/46 7038-4C 239/47 Z 7038- 4C 239/48 7038-4C 239/54 239/56 7038-4C 239/58 7038-4C 401/12 8829-4C 405/04 8829-4C // (C07D 401/12 213: 00 6701-4C 239: 00 ) 7038-4C (C07D 405/04 239: 00 7038-4C 317: 00) 7729-4C (72) Inventor Toshiyuki Umehara 1470 Shiraoka, Shiraoka-cho, Minamisaitama-gun, Saitama Nissan Biochemical Research Institute (72) Inventor Masaki Kudo 1470 Shiraoka, Shiraoka-cho, Minami-Saitama-gun, Saitama Prefecture, Institute for Biological Science, Nissan Chemical Industry Co., Ltd. (72) Yoichi Inoue 1470, Shiraoka, Shiraoka-cho, Minami-Saitama County, Saitama Prefecture, Institute for Biological Science, Nissan Chemical Industries, Ltd.

Claims (2)

[Claims] 1. A general formula [I]: << In the formula, R ¹ is a hydrogen atom, a C _{1 to} C ₄ alkyl group, a C _{2 to} C ₄ alkenyl group, a C _{2 to} C ₄ alkynyl group, a C _{1 to} C ₄ haloalkyl group, and a C _{2 to} C ₄ alkoxyalkyl group. , Formyl group, C ₂ -C ₆
Alkylcarbonyl, C ₂ -C ₆ alkoxycarbonyl group, C ₃ -C ₆ alkoxycarbonylalkyl group, C ₂ -C ₆ cyanoalkyl group, a benzyl group, a phenyl group, a cyano group,
Amino group, C ₃ -C ₆ alkoxycarbonyl group,
-SR ¹⁰ group {However, R ¹⁰ is C ₂ -C ₆ alkoxycarbonyl group, C ₁ -C ₆ alkylsulfonyl group, -NR ^{1 1} R ¹² group (wherein, R ¹¹ represents a C ₁ -C ₆ alkyl group , R ¹² is C ₁ -C ₆ alkyl groups, C ₂ -C ₆ alkoxycarbonyl groups, C ₃ -C ₉ alkoxycarbonylalkyl groups, C ₁ -C ₆ alkylsulfonyl groups, C ₂ -C ₆ alkylcarbonyl groups, C _{3 to} C ₉ dialkylaminocarbonyl group, C _{2 to} C ₆ dialkylaminosulfonyl group or an unsubstituted or optionally substituted phenyl group), or an unsubstituted or optionally substituted phenyl group (provided that As the optionally substituted substituent, a halogen atom, a cyano group, a nitro group, a C _{1 to} C ₄ alkyl group, a C _{1 to} C ₄ haloalkyl group, a C _{1 to} C ₄ alkoxy group, and a C ₁ to
C ₄ haloalkoxy group, C _{1 to} C ₄ alkylthio group, C _{1 to} C ₄ haloalkylthio group, C _{2 to} C ₆ alkoxycarbonyl group, C ₂
To C ₆ haloalkoxycarbonyl group, C _{2 to} C ₆ alkylcarbonyl group, C _{2 to} C ₆ haloalkylcarbonyl group, C _{1 to} C ₄ alkylsulfonyl group or C _{1 to} C ₄ haloalkylsulfonyl group, wherein the substituent is 2 In the case of one or more, the substituents may be the same or different). }, An alkali metal or an alkaline earth metal, and R ² is a hydrogen atom, a halogen atom, a C _{1 to} C ₄ alkyl group, or a C ₁ to
C ₄ haloalkyl group, C ₁ -C ₄ hydroxyalkyl group, C ₂ ~
C ₄ alkoxyalkyl group, C ₂ -C ₄ alkylthioalkyl group, a thiol group, C ₁ -C ₄ alkylthio group, C ₁ -C ₄ alkylsulfinyl group, C ₁ -C ₄ alkylsulfonyl group, C ₁ ~
C ₄ haloalkylthio group, C ₁ -C ₄ haloalkylsulfinyl group, C ₁ -C ₄ haloalkylsulfonyl group, hydroxy group, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy group, a formyl group, a cyano group, A nitro group, an amide group or a thiocyanate group, Z ¹ and Z ² each independently represent an oxygen atom, a sulfur atom or an imino group, and X represents a halogen atom, a C ₁ -C ₄ alkyl group, C ₁ -C ₄ alkoxy groups, C ₁ -C ₄ alkylthio group, C ₁ -C ₄ haloalkyl group,
C ₁ -C ₄ haloalkoxy groups, C ₁ -C ₄ haloalkylthio group,
Represents an amino group, a cyano group, or a nitro group, and l is 0 to
Represents an integer of 5 (provided that in the case of 2 to 5, X may be the same or different), and B is [However, Y is a halogen atom, C _{1 to} C ₆ alkyl group, C ₂ to
C ₆ alkenyl group, C ₂ -C ₆ alkynyl group, C ₃ -C ₆ cycloalkyl group, C ₁ -C ₆ haloalkyl group, C ₂ -C ₆ haloalkenyl group, C ₂ -C ₆ haloalkynyl group, C ₃ -C ₆ halocycloalkyl group, C ₂ -C ₆ cyanoalkyl group, C ₁ -C ₆ hydroxyalkyl group, C ₂ -C ₆ carboxyalkyl group, C ₁ -C ₆ alkoxy group, C ₂ -C ₆ alkenyloxy group, C ₂ -C ₆ alkynyloxy group, C ₃ -C ₆ cycloalkyl group, C ₁ -C ₆ haloalkoxy group, C ₂ -C ₆ haloalkenyloxy group, C ₂ -C ₆
Haloalkynyloxy group, C ₃ -C ₆ halocycloalkyl alkoxy group, C ₄ -C ₇ halocycloalkyl alkoxy group, C ₁ -C ₆ alkylthio group, C ₂ -C ₆ alkenylthio group, C ₂ -C ₆ alkynylthio group, C ₃ -C ₆ cycloalkylthio group, C ₁ -C ₆ haloalkylthio group, C ₁ -C ₆ alkylsulfinyl group, C ₂ ~
C ₆ alkenylsulfinyl group, C ₂ -C ₆ alkynylsulfinyl group, C ₃ -C ₆ cycloalkyl alkylsulfinyl group, C ₁ ~
C ₆ haloalkylsulfinyl group, C ₁ -C ₆ alkylsulfonyl group, C ₂ -C ₆ alkenylsulfonyl group, C ₂ -C ₆ alkynylsulfonyl group, C ₃ -C ₆ cycloalkylsulfonyl group, C ₁ -C ₆ haloalkylsulfonyl group, C ₂ -C ₆ alkoxyalkyl group, C ₂ -C ₆ alkoxyalkoxy, C ₂ -C ₆
Haloalkoxyalkyl group, C ₂ -C ₆ haloalkoxy alkoxy group, C ₂ -C ₆ alkylthioalkyl group, C ₂ -C ₆ alkylthioalkoxy group, C ₃ -C ₆ alkoxycarbonylalkyl group, C ₃ -C ₆ alkylcarbonyl alkyl group, C ₂ ~
C ₆ alkoxycarbonyl group, C ₂ -C ₆ alkylcarbonyloxy group, C ₂ -C ₆ alkylcarbonyl group, C ₃ -C ₆
Alkenylcarbonyl group, C ₃ -C ₆ alkynyl group, C ₄ -C ₇ cycloalkylcarbonyl group, C ₂ -C ₆ haloalkylcarbonyl group, C ₂ -C ₆ alkoxycarbonyl group,
C ₂ -C ₆ haloalkoxycarbonyl groups, C ₃ -C ₆ alkoxycarbonylalkoxy group, nitro group, cyano group, hydroxy group, carboxyl group, thiocyanate group, isothiocyanate group, C ₂ -C ₆ thiocyanate alkyl group, C ₁ ~
C ₆ alkylsulfonyloxy group, C ₂ -C ₆ alkylthiocarbonyl group, an amino group (-NR ³ R ^4), aminocarbonyl group (-
CONR ³ R ⁴ ), aminocarbonyloxy group (-OCONR ³ R ⁴ ), amide group (-NR ³ COR ⁴ ), alkoxycarbonylamino group (-NR
³ CO ₂ R ⁴ ), aminosulfonyl group (-SO ₂ NR ³ R ⁴ ), thioamide group (-NR ³ CSR ⁴ ), methylenedioxy group, halomethylenedioxy group, ethylenedioxy group, haloethylenedioxy Group, trimethylsilyl group or {However, W is Or [Chemical 5] (However, R ³ and R ⁴ are each independently a hydrogen atom, C _{1 to} C ₆
Alkyl group, C ₂ -C ₆ alkenyl group, C ₂ -C ₆ alkynyl group, C ₁ -C ₆ haloalkyl group, C ₂ -C ₆ haloalkenyl group,
C ₂ -C ₆ haloalkynyl group, C ₂ -C ₆ alkylcarbonyl group, C ₂ -C ₆ alkoxycarbonyl group, a phenyl group or a benzyl group, R ⁵ and R ⁶ are each independently hydrogen atom, a halogen atom , A C ₁ -C ₆ alkyl group, a C ₃ -C ₆ cycloalkyl group, a cyano group or a phenyl group, and q represents an integer of 0-2. ), N is an integer of 0 or 1, Ar is an unsubstituted or optionally substituted phenyl group, naphthyl group, furyl group, thienyl group, pyrrolyl group, pyrazolyl group, imidazolyl group, thiazolyl group, isothiazolyl group. Group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiadiazolyl group, triazolyl group, pyridyl group, pyridazyl group, pyrimidyl group, pyrazyl group, quinolyl group or quinoxalyl group (however, a substituent which may be substituted is a halogen atom, cyano group, nitro group, C ₁ -C ₄ alkyl group, C ₁ -C ₄ haloalkyl groups, C ₁ ~
C ₄ alkoxy, C ₁ -C ₄ Haroarukikoshi group, C ₁ -C ₄ alkylthio group, C ₁ -C ₄ haloalkylthio group, C ₁ -C ₄ alkylsulfonyl group, C ₁ -C ₄ haloalkylsulfonyl groups, C ₂
~ C ₄ alkoxycarbonyl group, carboxyl group, amino group, mono C ₁ -C ₄ alkylamino group, di C ₁ -C ₄ alkylamino group, phenyl group, benzyl group, methylenedioxy group or halomethylenedioxy group In the case where there are two or more substituents, the substituents may be the same or different. }, M is an integer of 0 to 5 (provided that Y ¹ may be the same or different in the case of 2 to 5). ] Or an unsubstituted or optionally substituted naphthyl group, a furyl group,
Thienyl group, pyrrolyl group, pyrazolyl group, imidazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, thiadiazolyl group, oxadiazolyl group, triazolyl group, pyridyl group, pyridazyl group, pyrimidyl group, pyrazyl group, quinolyl group, quinoxalyl group , A benzofuryl group, a benzothienyl group, an indolyl group, a benzoxazolyl group or a benzothiazolyl group (however, a substituent which may be substituted is a halogen atom, a cyano group, a nitro group, a C _{1 to} C ₄ alkyl group, C ₁ ~
C ₄ haloalkyl group, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy groups, C ₁ -C ₄ alkylthio group, C ₁ -C ₄ haloalkylthio group, C ₁ -C ₄ alkylsulfonyl group, C ₁ To C ₄ haloalkylsulfonyl group, C _{2 to} C ₄ alkoxycarbonyl group,
A carboxyl group, an amino group, a mono C ₁ -C ₄ alkylamino group, a di C ₁ -C ₄ alkylamino group, a phenyl group, a phenoxy group or a benzyl group is shown, and when there are two or more substituents, the substituents are the same. And X ₁ is a hydrogen atom or 3-bromo-4-methoxy, and B is a phenyl group. 2. A pest control agent containing one or more uracil derivatives according to claim 1 as active ingredients.