JP2006028056A - Pyrimidine derivative and pest controlling agent containing the same - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a compound having an excellent pest controlling activity. <P>SOLUTION: The pest controlling agent uses a pyrimidine derivative represented by formula [I] [wherein R<SP>1</SP>is an alkyl group or an alkoxy group; R<SP>2</SP>is an arylalkyl group or a heteroarylalkyl group; R<SP>3</SP>is hydrogen, a halogen or an alkyl group; n is 0, 1 or 2; and Het is represented by formulae [II] (wherein R<SP>4</SP>may be the same or different and is hydrogen, a hydroxyl group, a halogen, an alkyl group, an alkoxy group, an aryl group, a heteroaryl group, a cyano group, a nitro group, an amino group, an alkylamino group, a dialkylamino group, an alkylthio group, an alkylsulfinyl group or an alkylsulfonyl group; and m is an integer of 1-4)] or its salt. <P>COPYRIGHT: (C)2006,JPO&NCIPI

Description

The present invention relates to a pyrimidine derivative or a salt thereof, a production method thereof, and uses thereof.

しかし、特許文献１は、ピリミジン環２位の官能基が複素環基であるピリミジン誘導体を開示していない。
また、特許文献２は、ある種のピリミジン誘導体を含む殺菌剤を開示している。ここで特許文献２は、ピリミジン環６位の官能基が(C1-C4)アルキルスルホニル基、つまり-SO₂R基(RはC1-C4)であるピリミジン誘導体を開示する。しかし、特許文献２は、ピリミジン環６位の官能基が-SOnR基であってＲがアリールアルキル基又はヘテロアリールアルキル基であるピリミジン誘導体又はその塩について開示していない。 Conventionally, certain pyrimidine derivatives have been used in agricultural pests (aphids, weeviles, mites, etc.), sanitary pests (fly, cockroach, etc.), stored-grain pests (such as bryophytes, legumes), as well as agricultural and horticultural It has been used to control pests such as pathogenic bacteria (wheat red rust, barley powdery mildew, rice blast, etc.) (see Patent Documents 1 and 2).

However, Patent Document 1 does not disclose a pyrimidine derivative in which the functional group at the 2-position of the pyrimidine ring is a heterocyclic group.
Patent Document 2 discloses a bactericidal agent containing a certain kind of pyrimidine derivative. Here, Patent Document 2 discloses a pyrimidine derivative in which the functional group at the 6-position of the pyrimidine ring is a (C1-C4) alkylsulfonyl group, that is, a —SO ₂ R group (R is C1-C4). However, Patent Document 2 does not disclose a pyrimidine derivative or a salt thereof in which the functional group at the 6-position of the pyrimidine ring is a —SOnR group and R is an arylalkyl group or a heteroarylalkyl group.

JP 2001-247411 A German Patent Application No. 4034662

  An object of the present invention is to provide a compound having excellent activity against pests.

［式中、Ｒ¹はアルキル基又はアルコキシ基を表し；
Ｒ²はアリールアルキル基又はヘテロアリールアルキル基を表し；
Ｒ³は水素原子、ハロゲン原子又はアルキル基を表し；
nは０、１又は２を表し、
Hetは式[II]

（式中、R⁴は同一または異なってもよい水素原子、水酸基、ハロゲン原子、アルキル基、アルコキシ基を表し、アリール基、ヘテロアリール基、シアノ基、ニトロ基、アミノ基、アルキルアミノ基、ジアルキルアミノ基、アルキルチオ基、アルキルスルフィニル基又はアルキルスルホニル基を表し、mは１〜4の整数を表す）を表す］
で示されるピリミジン誘導体又はその塩、並びにこの１種以上を有効成分として含有する有害生物防除剤に関する。 As a result of intensive studies to find a compound having an excellent activity against pests, the present inventors have found that a novel pyrimidine derivative represented by the following formula [I] and a salt thereof have an excellent activity. It came to.
That is, the present invention
1. Formula [I]

[Wherein R ¹ represents an alkyl group or an alkoxy group;
R ² represents an arylalkyl group or a heteroarylalkyl group;
R ³ represents a hydrogen atom, a halogen atom or an alkyl group;
n represents 0, 1 or 2,
Het is the formula [II]

(Wherein R ⁴ represents a hydrogen atom, a hydroxyl group, a halogen atom, an alkyl group or an alkoxy group, which may be the same or different, and represents an aryl group, heteroaryl group, cyano group, nitro group, amino group, alkylamino group, dialkyl. Represents an amino group, an alkylthio group, an alkylsulfinyl group or an alkylsulfonyl group, and m represents an integer of 1 to 4.
And a pest control agent containing one or more thereof as an active ingredient.

[式中、Het、R¹、R³は上記１と同じ意味を表し、Xはハロゲン原子を表す]
で表される化合物と、
式[IV]

[式中、R²は上記１と同じ意味を表す]で表される化合物とを、塩基の存在下で反応せしめるか、または、式[V]

[式中、Het、R¹、R³は上記１と同じ意味を表す]で表される化合物と、
式[VI]

[式中、R²は上記１と同じ意味を表し、Xはハロゲン原子を表す]で表される化合物とを、塩基の存在下で反応せしめて、式[VII]

[式中、Het、R¹、R²、R³は上記１と同じ意味を表す]で表される化合物を得る工程；及び
(２)得られた式[VII]で表される化合物を酸化して、上記１に記載のピリミジン誘導体を得る工程；
を含む、上記１に記載のピリミジン誘導体又はその塩の製造方法に関する。 The present invention also provides:
2. (1) Formula [III]

[Wherein, Het, R ¹ , R ³ represent the same meaning as 1 above, and X represents a halogen atom]
A compound represented by
Formula [IV]

[Wherein R ² represents the same meaning as in the above 1], or a compound represented by the formula [V]

[Wherein Het, R ¹ and R ³ represent the same meaning as in the above 1],
Formula [VI]

[Wherein R ² represents the same meaning as in the above 1 and X represents a halogen atom] is reacted with a compound represented by the formula [VII]

[Wherein Het, R ¹ , R ² , R ³ represent the same meaning as in the above 1] to obtain a compound represented by:
(2) oxidizing the obtained compound represented by the formula [VII] to obtain the pyrimidine derivative described in 1 above;
The manufacturing method of the pyrimidine derivative or its salt of said 1 containing.

  The pyrimidine derivative or a salt thereof of the present invention is a novel compound, and exhibits an excellent pest control effect at a low dose compared to existing compounds. Moreover, since no phytotoxicity is observed for useful crops, it can be used as a pest control agent and has a low environmental impact.

で表されるピリミジン誘導体に関する。ここで、式[I]中、Ｒ¹は、アルキル基又はアルコキシ基を表す。Ｒ²は、アリールアルキル基又はヘテロアリールアルキル基を表す。Ｒ³は、水素原子、ハロゲン原子又はアルキル基を表す。nは、０、１又は２を表す。 (1) Pyrimidine derivatives represented by the above formula [I] and salts thereof
(1-1) Pyrimidine derivative represented by the formula [I] The present invention provides the following formula [I]:

It is related with the pyrimidine derivative represented by these. Here, in the formula [I], R ¹ represents an alkyl group or an alkoxy group. R ² represents an arylalkyl group or a heteroarylalkyl group. R ³ represents a hydrogen atom, a halogen atom or an alkyl group. n represents 0, 1 or 2.

を表す。ここで、式[II]中、R⁴は、水素原子、水酸基、ハロゲン原子、アルキル基、アルコキシ基を表し、アリール基、ヘテロアリール基、シアノ基、ニトロ基、アミノ基、アルキルアミノ基、ジアルキルアミノ基、アルキルチオ基、アルキルスルフィニル基又はアルキルスルホニル基を表す。mは１〜4の整数、好ましくは、1〜2の整数を表す。ｍが２以上の場合、各R⁴は、同一であっても異なっていてもよい。 Het has the formula [II]:

Represents. Here, in the formula [II], R ⁴ represents a hydrogen atom, a hydroxyl group, a halogen atom, an alkyl group or an alkoxy group, and an aryl group, heteroaryl group, cyano group, nitro group, amino group, alkylamino group, dialkyl An amino group, an alkylthio group, an alkylsulfinyl group or an alkylsulfonyl group is represented. m represents an integer of 1 to 4, preferably an integer of 1 to 2. When m is 2 or more, each R ⁴ may be the same or different.

Examples of the alkyl group mentioned in R ¹ , R ³ and R ⁴ include, for example, methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, t-butyl group, pentyl group, 1-ethylpentyl group, And C1-C10 alkyl groups such as 3,3-dimethylbutyl group.
Examples of the alkoxy group mentioned in R ¹ and R ⁴ include C1-C12 alkoxy groups such as a methoxy group, an ethoxy group, a propoxy group, and a t-butoxy group.
Examples of the arylalkyl group mentioned for R ² include phenylmethyl group, 2-phenylethyl group, 3-phenyl-n-propyl group, 4-phenyl-n-butyl group, α-naphthylmethyl group, β-naphthyl group. And C7-C20 arylalkyl groups such as a methyl group.
Examples of the heteroarylalkyl group mentioned for R ² include 2-furylmethyl group, 2-thienylmethyl group, 2-oxazolylmethyl group, 3-isoxazolylmethyl group, 1,2,3-oxa Diazole-4-methyl group, 2-pyridylmethyl group, 4-pyridylmethyl group, 2-pyridinylmethyl group, 4-pyridinylmethyl group, 3-pyrazolylmethyl group, 2-thiazolylmethyl group, 2-imidazolylmethyl group, 3- ( And C2-C19 heteroarylalkyl groups such as 1,2,4-triazolyl) methyl group and 2-quinolinylmethyl group.

The halogen atom mentioned in R ³ , R ⁴ and Hal means a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.
Examples of the aryl group referred to as R ⁴ include C6-C10 aryl groups such as a phenyl group, an α-naphthyl group, and a β-naphthyl group.
Examples of the heteroaryl group mentioned for R ⁴ include 2-furyl group, 2-thienyl group, 2-oxazolyl group, 3-isoxazolyl group, 1,2,3-oxadiazol-4-yl group, 2- C1-C9 such as pyridyl group, 4-pyridyl group, 2-pyrimidinyl group, 3-pyrazolyl group, 2-thiazolyl group, 2-imidazolyl group, 3- (1,2,4-triazolyl) group, 2-quinolinyl group A heteroaryl group.
Examples of the alkylene group of the alkylamino group, dialkylamino group, alkylthio group, alkylsulfinyl group and alkylsulfonyl group mentioned in R ⁴ include, for example, a methylene group, an ethylene group, a propylene group, an isopropylene group, a butylene group, an isobutylene group, C1-C10 alkylene groups such as t-butylene group, pentylene group, 1-ethylpentylene group and 3,3-dimethylbutylene group; vinylene group, 1-propenylene group, 2-propenylene group, isopropenylene group, 1- Alkenylene groups such as butenylene group, 2-butenylene group, 1-hexenylene group, 1-octenylene group; ethynylene group, 1-propynylene group, 2-propynylene group, 1-butynylene group, 2-butynylene group, 3-butynylene group, Examples include alkynylene groups such as 4-methyl-1-pentynylene group and 3-methyl-1-pentynylene group.

The alkyl group, alkoxy group, arylalkyl group, heteroarylalkyl group, aryl group and heteroaryl group mentioned in R ¹ , R ² , R ³ and R ⁴ may be further substituted with a substituent. Examples of substituents that can be used include:
Halogen atom [fluorine atom, chlorine atom, bromine atom, etc.];
An alkyl group [for example, methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, sec-butyl group, i-butyl group, t-butyl group, pentyl group, 1,1-dimethylpropyl group , C1-C10 alkyl groups such as 1-methylpentyl group, 3,3-dimethylbutyl group, heptyl group];
Haloalkyl group [for example, C1-C10 such as trifluoromethyl group, difluoromethyl group, difluorobromomethyl group, fluoromethyl group, 2,2,2-trifluoroethyl group, 1,1,2,2-tetrafluoroethyl group, etc. A haloalkyl group];
A cycloalkyl group [for example, a C3-C10 cycloalkyl group such as a cyclopropyl group, a cyclopentyl group, a cyclohexyl group];
Alkoxy groups [for example, C1-C10 alkoxy groups such as methoxy group, ethoxy group, n-propoxy group, i-propoxy group, n-butoxy group, sec-butoxy group, i-butoxy group, t-butoxy group];
Haloalkoxy groups [for example, trifluoromethoxy group, difluoromethoxy group, difluorobromomethoxy group, difluorochloromethoxy group, fluoromethoxy group, 2,2,2-trifluoroethoxy group, 1,1,2,2-tetrafluoroethoxy A C1-C10 haloalkoxy group such as a group];

Alkylthio groups [for example, C1-C10 alkylthio groups such as methylthio group, ethylthio group, n-propylthio group, n-butylthio group, sec-butylthio group, i-butylthio group, t-butylthio group];
Haloalkylthio group [for example, trifluoromethylthio group, difluoromethylthio group, difluorobromomethylthio group, difluorochloromethylthio group, 2,2,2-trifluoroethylthio group, 1,1,2,2-tetrafluoroethylthio group, etc. A C1-C10 haloalkylthio group of
Alkylamino group [for example, methylamino group, ethylamino group, n-propylamino group, i-propylamino group, n-butylamino group, sec-butylamino group, i-butylamino group, t-butylamino group, n -C1-C10 alkylamino group such as pentylamino group];
Dialkylamino groups [eg C2-C20 dialkylamino groups such as dimethylamino group, diethylamino group, methylethylamino group, ethyl-n-propylamino group];
Alkoxycarbonyl groups [for example, methoxycarbonyl group, ethoxycarbonyl group, n-propoxycarbonyl group, i-propoxycarbonyl group, n-butoxycarbonyl group, sec-butoxycarbonyl group, i-butoxycarbonyl group, t-butoxycarbonyl group, etc. C2-C10 alkoxycarbonyl group];
A haloalkoxycarbonyl group [for example, a C2-C10 haloalkoxycarbonyl group such as 2,2,2-trifluoroethoxycarbonyl group];
Alkylaminocarbonyl group [for example, methylaminocarbonyl group, ethylaminocarbonyl group, n-propylaminocarbonyl group, i-propylaminocarbonyl group, n-butylaminocarbonyl group, sec-butylaminocarbonyl group, i-butylaminocarbonyl group , C2-C10 alkylaminocarbonyl groups such as t-butylaminocarbonyl group and n-pentylaminocarbonyl group];

Dialkylaminocarbonyl group [C3-C10 dialkylaminocarbonyl group such as dimethylaminocarbonyl group, diethylaminocarbonyl group, methylethylaminocarbonyl group, ethyl-n-propylaminocarbonyl group];
An acylamino group [for example, C2-C10 acylamino group such as acetylamino group, propanoylamino group, n-butanoylamino group];
An alkoxycarbonylamino group (for example, a C2-C10 alkoxycarbonylamino group such as a methoxycarbonylamino group, an ethoxycarbonylamino group, an n-propoxycarbonylamino group, an i-propoxycarbonylamino group, an n-butoxycarbonylamino group);
A cyano group; a nitro group and a hydroxyl group. Two or more substituents, which may be the same or different, may be present simultaneously.

（式中、Het、R¹、R²、R³、ｎは、上記式[I]で説明したのと同じ意味を表し；Ａ及びＡ’は、いずれか一方がＮＨ⁺でありかつ他方がＮであり；Ｂ^-は、酸性イオンであり、好ましくは、Ｘ^-、Ｒ⁵ＳＯ₃ ^-又はＲ⁶ＣＯＯ^-（ここで、Ｘはハロゲン原子であり、R⁵は、例えば、OH基、アルキル基、好ましくはC1-C5のアルキル基、アリル基、好ましくはフェニル基)であり、R⁶は、例えば、C1〜C10、好ましくはC1〜C5のアルキル基であり得る）である）で示すことができる。
本発明の上記式[I]で示されるピリミジン誘導体及びその塩は、不斉原子に基づく光学異性体（Ｒ，Ｓ）や飽和環に基づく幾何異性体（シス，トランス）の形態を取り得る。本発明で言うピリミジン誘導体及びその塩の語は、有害生物防除活性を有するこれらすべての光学異性体、幾何異性体およびこれらの混合物を含むものである。 (1-2) Salt of pyrimidine derivative represented by formula [I] The salt of pyrimidine derivative represented by formula [I] of the present invention is an inorganic salt of the pyrimidine derivative such as hydrochloric acid or sulfuric acid, or acetic acid or fumaric acid. Or an organic salt. Specifically, for example, the following formula [I] ′

(In the formula, Het, R ¹ , R ² , R ³ , n represent the same meaning as described in the above formula [I]; one of A and A ′ is NH ⁺ and the other is N is; B ⁻ is an acidic ion, preferably X ⁻ , R ⁵ SO ₃ ^— or R ⁶ COO ⁻ (where X is a halogen atom, R ⁵ is, for example, an OH group, alkyl Group, preferably a C1-C5 alkyl group, an allyl group, preferably a phenyl group), and R ⁶ can be, for example, a C1-C10, preferably a C1-C5 alkyl group)) Can do.
The pyrimidine derivatives represented by the above formula [I] and salts thereof of the present invention can take the form of optical isomers (R, S) based on asymmetric atoms and geometric isomers (cis, trans) based on saturated rings. The term pyrimidine derivatives and salts thereof in the present invention includes all these optical isomers, geometric isomers and mixtures thereof having pesticidal activity.

(1-3) Specific examples of pyrimidine derivatives represented by formula [I] and salts thereof Specific examples of pyrimidine derivatives represented by formula [I] of the present invention and salts thereof are shown in Tables 1 to 3. However, the present invention is not limited to these. In the table, Me represents a methyl group, Et represents an ethyl group, Pr represents a propyl group, and Bu represents a butyl group. N- represents normal-, i- represents iso-, s- represents secondary-, t- represents tertiary-, and c- represents cyclo-.

[Table 1] Specific examples of pyrimidine derivatives having the following formula [VIII] and salts thereof

[Table 2] Specific examples of pyrimidine derivatives having the following formula [IX] and salts thereof

[Table 3] Specific examples of pyrimidine derivatives having the following formula [X] and salts thereof

The pyrimidine derivative of the present invention or a salt thereof preferably has a fluorine-based substituent such as —F group or —CF ₃ group. The fluorine-based substituent is preferably contained in R ₁ or R ₂ . In the formula [I], n is 1 or 2, and, -SO- or -SO ₂ - preferably have a. Furthermore, the pyrimidine derivative of the present invention or a salt thereof preferably has a hydrophilic group such as an alkoxy group.

(2) Method for producing pyrimidine derivative represented by formula [I] or a salt thereof The pyrimidine derivative represented by formula [I] of the present invention can be produced according to the following steps (1) and (2). .

Process (1)

ここで、各式中、Ｒ¹、Ｒ²、Ｒ³、Het、ｎは、上記式[I]で説明したのと同じ意味を表し、Ｘは、ハロゲン原子(フッ素原子、塩素原子、臭素原子又はヨウ素原子)を表す。
以下、これらの工程(１)及び(２)を詳述する。 Process (2)

Here, in each formula, R ¹ , R ² , R ³ , Het, n represent the same meaning as described in the above formula [I], and X represents a halogen atom (a fluorine atom, a chlorine atom, a bromine atom). Or an iodine atom).
Hereinafter, these steps (1) and (2) will be described in detail.

[式中、Het、R¹、R²、R³は上記式[I]で説明したのと同じ意味を表す]で表される化合物が、ルートＡ又はルートＢを経て調製される。 (2-1) Step (1) In step (1), the following formula [VII]:

[Wherein, Het, R ¹ , R ² , R ³ represent the same meaning as described in the above formula [I]] is prepared via route A or route B.

[式中、Het、R¹、R³は上記式[I]で説明したのと同じ意味を表し、Xはハロゲン原子(フッ素原子、塩素原子、臭素原子又はヨウ素原子)を表す]
で表される化合物と、下記式[IV]：

[式中、R²は上記式[I]で説明したのと同じ意味を表す]で表される化合物とを、塩基の存在下で反応せしめて、上記式[VII]で表される化合物を得るものである。 (2-1-1) Route A
Route A is represented by the following formula [III]:

[Wherein, Het, R ¹ and R ³ represent the same meaning as described in the above formula [I], and X represents a halogen atom (a fluorine atom, a chlorine atom, a bromine atom or an iodine atom)]
And a compound represented by the following formula [IV]:

[Wherein R ² represents the same meaning as described in the above formula [I]] and a compound represented by the above formula [VII] by reacting in the presence of a base. To get.

Examples of the base used in this reaction include triethylamine, diisopropylethylamine, pyridine, N, N-dimethylaniline, 1,8-diazabicyclo- [5.4.0] undecene-7 (DBU), potassium carbonate, sodium carbonate and the like. Examples thereof include carbonates; hydroxides such as sodium hydroxide and potassium hydroxide; hydrides such as sodium hydride; metal alkoxides such as sodium methoxide, sodium ethoxide and potassium t-butoxide. The amount of the base used is, for example, usually 0.1 to 100 mol, preferably 0.5 to 10 mol, per 1 mol of the compound represented by the formula [III].
The reaction temperature is suitably in the range from 0 ° C. to the boiling point of the solvent used, because the reaction proceeds smoothly, but is preferably 15 to 25 ° C.
The reaction time is usually 1 minute to 100 hours, preferably 1 to 24 hours.

The reaction may be performed according to a reaction mode described in, for example, JP-A-2001-247411. For example, the compounds represented by Formula [III] and Formula [IV] may be dissolved in a solvent, and the base may be further added to proceed the reaction at a predetermined reaction temperature and reaction time. Examples of the solvent that can be used include amides such as dimethylformamide (DMF) and N-methylpyrrolidone; ethers such as THF and diethyl ether; aromatic hydrocarbons such as benzene, toluene and xylene; Esters; Nitriles such as acetonitrile; DMSO and the like. As the solvent, for example, it is appropriate to use an amount such that the amount of the substrate is 0.1 to 100 mol / l, preferably 1 to 10 mol / l.
When the compound represented by the formula [III] is prepared as a non-halogenated precursor, a halogenating agent such as chlorine, thionyl chloride, phosphoryl chloride, phosphorus oxychloride, phosphorus pentachloride, bromine and iodine is used. It may be halogenated to obtain a compound represented by the formula [III].
After completion of the reaction, the reaction solution containing the target product is subjected to solvent distillation or solvent extraction, etc., and the obtained residue is purified by recrystallization method, column chromatography method, etc. as necessary to produce the target product. be able to.

[式中、Het、R¹、R³は上記式[I]で説明したのと同じ意味を表す]で表される化合物と、式[VI]：

[式中、R²は上記式[I]で説明したのと同じ意味を表し、Xはハロゲン原子を表す]で表される化合物とを、塩基の存在下で反応せしめて、上記式[VII]で表される化合物を得るものである。
この反応に用いられる塩基の種類、反応温度、反応時間及び反応様式は、上記ルートＡと同様である。また、使用する塩基の量は、例えば、式［V］で表される化合物１モルに対して通常0.1〜100モル、好ましくは、０．５〜１０モルであることが適当である。 (2-1-1) Route B
On the other hand, the route B is represented by the following formula [V]:

[Wherein, Het, R ¹ and R ³ have the same meaning as described in the above formula [I]], and a compound represented by formula [VI]:

[Wherein R ² represents the same meaning as described in the above formula [I], and X represents a halogen atom]. In the presence of a base, the compound represented by the above formula [VII The compound represented by this is obtained.
The kind of base used in this reaction, the reaction temperature, the reaction time, and the reaction mode are the same as those in Route A. The amount of the base used is, for example, usually 0.1 to 100 mol, preferably 0.5 to 10 mol, per 1 mol of the compound represented by the formula [V].

(2-2) Step (2) The compound represented by the formula [VII] obtained in the above step (1) is oxidized to obtain a pyrimidine derivative represented by the formula [I]. Here, the oxidation may be performed in the presence of an oxidizing agent and a catalyst. Examples of the oxidizing agent include hydrogen peroxide, hydroperoxide, ozone, potassium peroxosulfate, potassium permanganate, chromic acid, sodium dichlorite, nitric acid, dinitrogen tetroxide, sodium metaperiodate, ruthenium oxide and Examples thereof include osmium oxide. Examples of the catalyst include sodium tungstate dihydrate, molybdic acid, vanadium pentoxide and the like.
Further, as the oxidation reaction, the methods described in Croat. Chem. Acta 1962, 34, 115 and Bioorg. Med. Chem. Lett. 2002, 12 (12), 1595 can also be used.
The reaction temperature is 0 to 100 ° C, preferably 15 to 25 ° C.
The reaction time is usually 1 minute to 100 hours, preferably 1 to 24 hours.

The raw material compounds represented by the formulas [III] to [VI] used for producing the pyrimidine derivative represented by the formula [I] of the present invention can be appropriately used from those commercially available. If available, a commercially available compound represented by the formula [VII] may be obtained to produce a pyrimidine derivative represented by the formula [I].
For example, the compound represented by the formula [IV] is a so-called mercaptan, and can be obtained in high yield from the corresponding halogen compound such as the formula [VI] according to the description of Journal fuer Praktiche Chemie, 1958, 7, 191-195. Can do.

(2-3) Method for producing salt of pyrimidine derivative represented by formula [I] of the present invention The pyrimidine derivative represented by formula [I] obtained as described above is further reacted with various acids. A salt of a pyrimidine derivative represented by the formula [I] can be produced. Examples of the acid include hydrogen chloride, hydrogen bromide, sulfuric acid, nitric acid, acetic acid, fumaric acid and the like.
Examples of the reaction include those shown in Aust. J. Chem., 1982, 35, 1203-1207.

(3) Pest control agent TECHNICAL FIELD This invention relates to the pest control agent which contains the pyrimidine derivative represented by the said Formula [1], or 1 type, or 2 or more types of its salt as an active ingredient.
Here, the term organism is meant to include animals and plants. Therefore, the term “pesticidal agent” specifically refers to fungicides and fungicides for plant protection, insecticides, acaricides, nematicides, herbicides for fields and non-agricultural land, and aquatic organisms. Is used to include an antifouling agent for preventing water from adhering to underwater contact objects such as ship bottoms and fishing nets.
Here, the pests include, but are not limited to, fungi and fungi such as Eumycota, Myxomycota, Bacteriomycota, Actinomycota, and the like; Agricultural pests, sanitary pests, stored grain pests, clothing pests, house pests and other pests; broad-leaved weeds, upland weeds, paddy weeds, and other aquatic organisms; It is done.

(3-1) Fungi and molds Fungi and molds include, for example, the following fungi (Eumycota), Myxomycota, Bacteriomycota, Actinomycota, and other fungi and fungi Kind.
Rice blast (Pyricularia oryzae), sesame leaf blight (Cochliobolus miyabeanus), blight (Rizoctonia solani), etc .; wheat powdery mildew (Erysiphe graminis), red mold (Gibberella zeae), (red) rust Disease (Puccinia striiformis, P.graminis, P. recondita, P. hordei), snow rot (Typhula sp., Micronectriella nivalis), naked smut (Ustilago tritici, U. nuda), scab (Tilletia caries), Eye disease (Pseudocercosporella herpotrichoides), cloud disease (Rhynchosporium secalis), leaf blight (Septoria tritici), blight (Leptosphaeria nodorum), net blotch (Pyrenophora teres), and potato rot (Helminthosporium zonatum Ikata); Black spot (Diaporthe citri), common scab (Elsinoe fawcetti), fruit rot (Penicillium digitatum, P. italicum), brown rot (Phytophthora citrophthora ,, P. nicotianae), black scab (Phyllostictina citricarpa) Xanthomonas citri), etc .; apple Monilia disease (Monilinia mali), rot (Valsa mali), udon Powdery mildew (Podosphaera leucotricha), spotted leaf disease (Alternaria mali), black spot disease (Venturia inaequalis), black spot disease (Mycospherella pomi), anthracnose (Colletotrichum acutatum), ring rot (Botryosphaeria berengeriana), red star disease (Gymnosporangium) yamadae), black spot disease (Monilinia fructicola), etc .; pear black spot disease (Venturia nashicola, V. pirina), black spot disease (Alternaria kikuchiana), red star disease (Gymnosporangium haraeanum), black star disease (Monilinia fructigena), etc .; Of black rot (Monilinia fructicola), black scab (Cladosporium carpophilum), phomopsis sp. (Phomopsis sp.), Etc .; grape black rot (Elinoe ampelina), late rot (Colletotrichum acutatum), powdery mildew (Uncinula necator) ), Rust disease (Phakopsora ampelopsidis), black lot disease (Guignardia bidwellii), downy mildew (Plasmopara viticola), ash star disease (Monilinia fructigena), black star disease (Cladosporium viticolum), gray mold disease (Botrytis cinerea), etc .; Anthracnose (Gloeosporium kaki), Deciduous leaf (Cercospora kaki, Mycosh) aerella nawae), etc .; Colletotrichum lagenarium, powdery mildew (Sphaerotheca fuliginea, Oidiopsis taurica), vine blight (Didymella bryoniae), vine split (Fusarium oxysporum), downy mildew (Pseudoperonospora cuben) , Plague (Phytophthora sp.), Seedling blight (Pythium sp.), Etc .; ring tomato disease (Alternaria solani), leaf mold (Cladosporium fulvum), plague (Phytophthora infestans), etc .; Phomopsis vexans), powdery mildew (Erysiphe cichoracearum), etc .; Brassicaceae vegetable black spot disease (Alternaria japonica), white spot disease (Cercosporella brassicae) soft rot disease (Erwinia carotovora), etc .; leek rust disease (Puccinia allii), etc .; soybean Purpura (Cercospora kikuchii), black scab (Elsinoe glycines), black spot (Diaporthe phaseolorum var. Sojae), etc .; bean anthracnose (Colletotrichum lindemthianum), etc .; groundnut black rot (Cercospora personata), brown spot Disease (Cercospora arachidicola) etc .; Pea powdery mildew (Erysiphe pisi) etc .; Potato summer plague (Alternaria solani), plague (Phytophthora infestans), leaf rot fungus (Rhizoctonia solani), etc .; Strawberry powdery mildew (Sphaerotheca humuli), etc .; Cha net rot (Exobasidium reticulatum), white scab (Elsinoe leucospila) Etc .; tobacco red star disease (Alternaria longipes), powdery mildew (Erysiphe cichoracearum), anthracnose (Colletotrichum tabacum), downy mildew (Peronospora tabacina), plague (Phytophthora nicotianae), wildfire (Pseudomonus syringae), etc .; Sugar beet brown spot (Cercospora beticola), seedling blight (Aphanomyces cochliodes), rose black spot (Diplocarpon rosae), powdery mildew (Sphaerotheca pannosa), etc .; chrysanthemum spot (Septoria chrysanthemi-indici), White rust (Puccinia horiana), etc .; Gray rot (Botrytis cinerea) of various crops, Sclerotinia sclerotiorum, etc.

(3-2) Pest The pest control agent of the present invention can be used to control pests such as agricultural pests, hygiene pests, stored grain pests, clothing pests and house pests. The pesticidal agent of the present invention has an effect of killing insects, larvae, larvae and ovaries. Although the following are mentioned as a typical example of a pest, it is not limited to these.
Lepidopterous pests; for example, Spodoptera litura, Mamestra brassicae, Agrotis ipsilon, Pseudaletia separata, Trichoplusia ni, Plutella xylostella, Plutella xylostella sp. Euproctis pseudoconspersa, Chilo suppresalis, Conaphalocrocis medinalis, Hyphantria cunea, Hellula undalis, Heliothis, Helicoverpa gro, Agrotis, Grotis (Tiena translucens), Kodri Nga (Laspeyresia pomonella), cotton beetle (Pectinophora gossypiella) and the like.
Hemiptera: Pseudopod aphids (Myzus persicae), cotton aphids (Aphis gossyppi), black-headed aphids (Lipaphis erysimi), barley beetles (Rhopalosiphum padi), horned beetles (Riptortus clavatus) Nezara viridula), Alaska scales (Unaspis yanonensis), Staghorn scales (Pseudococcus comstocki), Whitefly (Trialeurodes vaporariorum), Tobacco whitefly (Bemisia tabaci), Psylla pyrisuga, nashi Stephani, nashi ), Brown planthopper (Laodelphax striatellus), white-tailed planthopper (Sogatella furcifera), leafhopper (Nephotetix cincticeps) and the like.

Coleoptera: For example, corn root worm (Diabrotica sp.), Cucumber beetle (Aulacophora femoralis), Colorado potato beetle (Leptinotarsa decemlineata), rice weevil (Lissorhoptrus oryzophilus), weevil (Sitophilus zeamais), callo bruzo japonica, Anomala rufocuprea, Tobacco beetle (Lasioderma serricorne), Lyctus brunneus, Monochamus alternatus, Anoplophora malasiaca, Agripl vigintioctopunctata), coconut (Tenebroides mauritanicus), cotton weevil (Anthonomus grandis), etc.
Diptera: Musca domestica, Ceratitis capitata, Dacus cucurbitae, Dacus dorsalis, Hylemya platura, Lily flies Drosophila suzukii, Stomoxys sp., Culex tritaeniorhynchus, Aedes aegypti, Anopheles slnensis and the like.
Common pests; for example, Thrips palmi, Scirtothrips dorsalis, Helothothrips haemorrhoidalis, Frankliniella occidentalis, etc.
Hymenoptera: For example, Camponotus kiusiuensis, Vespa simillima xanthoptera, Athalia rasaejaponensis and the like.

For example, Blatella germanica, American cockroach (Periplaneta Americana), Black cockroach (Periplanrta fuliginosa), Grasshopper (Locustamigratoria migratoriodes), etc.
Isoptera pests; for example, termites (Coptotermen formosanus), termites (Reticulitermess peratus), etc.
Lice pests; for example, Pediculs humanus corporis, Pthirus pubis, etc.
Tick; for example, Tick spider mite (Tetranychus ulticae), Kantawa spider mite (Tetranychus kannzawai), Scarlet spider mite (Panonychus ulmi), Ripe spider mite (Phyllocoptruta oleivora), Rust spider mite (Aculus schlech (Brevipalpus), Eotetranycus, Rhizoglyphus robini, Tyrophagus putrescentiae, Boophilis microplus, Haemaphysalis longicornis and the like.
Plant-parasitic nematodes; for example, Meloidogyne incognita, Pratylenchus sp., Heterodera glycines, Aphelenchoides besseyi, Bursaphel etc. x
In addition, it is also effective against various pests having resistance to existing pests and mite control agents.

(3-3) Weeds The pest control agent of the present invention can be used as a herbicide for upland and non-agricultural land that can be used in known treatment methods such as soil treatment and foliage treatment. Although the following are mentioned as a typical example of the weed which can be controlled, it is not limited to these.
(3-3-1) Broad-leaved weed Solanum weeds; for example, Solanum nigrum L., Daturastra monium, etc.
Mallow weed; for example, Abutilon theophrasti, American deer (Sida rhombifolia L.), velvet leaf (Abutilon theophrastic) and the like.
Convolvulaceae weeds; for example, morning glory (Ipomea purpurea, I. Iacunosa, Pharbitis purpurea), convolvulus (Calystegia japonica Choisy, C. sepium var. Japonica Makino, Convolvulus arvensis L.), etc.
Amaranthus weeds; for example, Amaranthus blitum L., Amaranthus gracilis Defs., A. retroflexus, A. viridis L.
Asteraceae weeds; for example, Onamomi (Xanthium pensylvanicum, X. strumarium), Ragweed (Ambrosia artemisiifolia L var. , Himejiyon (Aster annuus L.) etc.
Brassicaceae weeds; for example, Rorippa indica Hieron, Sinapis arvense, Capsella bursa-pastoris Medic.
For example, Polygonum blumei Meisn., P. longisetum De Bruyn., Buckwheat (Polygonum convolvulus), etc.
Physalis weed, for example, Portulaca oleracea L.
Rubiaceae weeds; for example, Shiroza (Chenopodium album L.), Koakaza (Chenoposium ficifolium), Butterflies (Kochia scoparia) and the like.
Radish weeds; for example, Stellaria media.
Species weeds; for example, Veronica persica Poir.
Aspergillus weed; for example, Commelina communis L.
Lamiaceae weeds; for example, Laplacia (Lamium amplexicaule L.), Laminum purpurem, etc.
Euphorbiaceae weeds; for example, Kamaesyce supine Mold., Euphorbia supine Rafin., Euphorbia maculata, etc.
Rubiaceae weeds; for example, Yamgra (Galium aparine L., G. Vaillanta DC.), Akane (Rubia akane) and the like.
Violet weeds; for example, Violet (Viola mandshurica).
Leguminous weeds; for example, Sesbania exaltata, Cassia obtusifolla, etc.

(3-3-2) Upland field weeds: Gramineae weeds; for example, wild sorghum (Porgum dichotomiflorum), Johnsongrass (Sorgham halepense), Echinochloa crus-galli var. Crus galli, Echinochloa crus-galli var.praticola), cultivated shrimp (Echinochloa utilis), bark (Digitaria adscendens Henr., D. marginata Fernald), oats (Avena fatua L., A. sativa), bark (Eleusine indica Gaertn.) Setaria ciridis, S. faberi, S. pumila, S. viridis Beauv.), Sparrows (Alopecurus aequalis Sobol. Var.
Cyperaceae weeds; for example, Cyperus rotundus, Cyperus esculentus.

(3-3-3) Paddy Field Weed The pest control agent of the present invention can be used as a paddy field herbicide by using a known treatment method such as soil treatment or foliage treatment under irrigation. Although the following are mentioned as a typical example of a paddy weed, It is not limited to these.
Omodaka weeds; for example, Heramodaka (Alisma canaliculatum A. Br. Et Bouche), Omodaka (Sagittaria trifolia L.), Urikawa (Sagittaria pygmaea Miq.) And the like.
Cyperaceae weeds; for example, Cyperus difformis L., Cyperus serotinus Rottb., Scirpus juncoides Roxb.
For example, Azena (Lindernia procumbens Philcox).
Cyprinid weeds; for example, Monochoria vaginalis Presl.
Hymenoptera weeds; for example, Hiramushiro (Potamogeton franchetii A. Benn. Et Baag., P. longipetiolatus A. Camus).
For example, Rotala indica Koehne.
Echinochloa crus-galli Beauv. Var. Oryzicola Ohwi, Echinochloa crus-galli Beauv. Var. Kasaharae Ohwi, E. crus-galli Beauv. Var. Ohwi), Echinochloa crus-galli weeds, etc.

In particular, the pyrimidine derivatives or salts thereof of the present invention include fungi such as tomato plague, wheat leaf rust, barley powdery mildew, cucumber downy mildew, cucumber and kidney bean gray mold, kidney bean leaf rot and the like; It is useful for red weeds such as family weeds and shiroza.
The pest control agent of the present invention has high safety against useful crops such as rice, wheat, barley, solgo, peanut, corn, soybean, beet, cotton, apple, pear, mandarin orange, and grape. ing.

(3-4) Form of the pest control agent When the pest control agent of the present invention is actually applied, it is used in a pure form without adding other components, or a form that can be taken by general agricultural chemicals. That is, it can also be used in the form of solid agents such as granules and powders; liquid agents such as wettable powders, wettable powder granules, emulsions, aqueous solvents, emulsion formulations, oils, aerosols, sprays, and flowables. .
When used in the form of a solid agent, as additives and carriers, for example, plant powders such as wood flour and corn cob; minerals such as diatomaceous earth, calcined stone, gypsum, talc, bentonite, pyrophyllite, clay Organic powders; organic and inorganic compounds such as potassium chloride, urea, and sodium sulfate can be used.
When used in the form of a liquid agent, examples of the solvent include petroleum fractions such as kerosene, chelesin and solvent naphtha, cyclohexane, N-methylpyrrolidone, dimethyl sulfoxide, alcohol, acetone, methyl isobutyl ketone, mineral oil, vegetable oil, water, etc. Can be used. Furthermore, a surfactant can be added as necessary to ensure the uniformity and stability of the solution.

(3-5) Content and Application Rate of Pest Control Agent The pest control agent of the present invention depends on the form of the pest control agent and the type of pyrimidine derivative or salt thereof used, but the above formula [1] Is contained, for example, 0.1 to 70 mass%, preferably 1 to 40 mass%. When the pesticidal agent of the present invention is in the form of solid agents such as granules and powders, the pesticidal agent of the present invention contains 1 to 10 mass of the pyrimidine derivative represented by the above formula [1] or a salt thereof. %, Preferably 1 to 5% by mass, and more preferably, the pyrimidine derivative represented by the formula [1] or a salt thereof may be used as it is (100% by mass) as a pest control agent. Furthermore, when the pest control agent of the present invention is in the form of a liquid and is appropriately diluted with a solvent such as water, the pest control agent of the present invention is a pyrimidine derivative represented by the above formula [1] or a derivative thereof. For example, the salt may be contained in an amount of 0.1 to 500 ppm, preferably 10 to 250 ppm.
The pest control agent of the present invention comprises a pyrimidine derivative represented by the above formula [1] or a salt thereof as an active ingredient and contains an effective amount thereof. Here, the pyrimidine derivative represented by the formula [1] or a salt thereof is included as an active ingredient, that is, including the effective amount thereof means that the above-mentioned sterilization, fungicidal, insecticidal, acaricidal, nematicidal, herbicidal, antibacterial It means that the pyrimidine derivative represented by the above formula [1] or a salt thereof is contained in an amount capable of sufficiently exerting the fouling effect. The effective amount depends on the type of pyrimidine derivative or salt thereof used or the type of pest, but specifically, the pyrimidine derivative represented by the above formula [1] or its per one hectare of land to be applied. It is suitable to apply the salt in an amount of 0.1 to 3000 g, preferably 100 to 1500 g. These application rates and application concentrations vary depending on the type of preparation, application time, application location, application method, pest type, damage level, etc., and can be increased or decreased regardless of the above range. can do.

(3-6) Application method of pest control agent When the compound of the present invention is used as an agricultural pest control agent, it depends on the type of pest control agent used, but the pyrimidine derivative represented by the formula [1] Or its salt is preferably applied in an amount of usually 100 g to 1500 g per hectare of farmland. When used as an insecticide for epidemics, it is preferably in the form of an emulsion, a wettable powder, or a flowable agent, mixed with a solvent such as water, and the concentration of the pyrimidine derivative represented by the formula [1] or a salt thereof is 0.1 ppm to It is suitable to dilute to 500 ppm and use as a suspension or emulsion. When used as granules, powders, oils, aerosols, sprays or poison baits, the above-mentioned preparations of the pest control agent of the present invention such as granules and oils may be applied as they are.

(3-7) Other drugs It goes without saying that the pest control agent of the present invention is sufficiently effective by itself. It can also be used as a mixture with one or more plant growth regulators or synergists.
Although the typical example of the chemical | medical agent which can be mixed with the pest control agent of this invention is shown below, it is not limited to these.

(3-7-1) Disease control agent:
Copper disease control agent; basic copper chloride, cupric hydroxide, basic copper sulfate, anhydrous copper sulfate, oxine copper, nonylphenol sulfonate copper, DEBDC, quicklime, etc.
Inorganic agent: sulfur, polysulfide lime, zinc sulfate, sodium hydrogen carbonate, potassium hydrogen carbonate, sodium hypochlorite and the like.
Organic sulfur-based agents: dineb, manneb, manzeb, ambam, polycarbamate, organic sulfur nickel salt, propineb, ziram, thiuram, thiadiazine, etc.
Organophosphorous agents: IBP, EDDP, tolcrofosmethyl, fosetyl, etc.
Melanin synthesis inhibitor; fusaride, tricyclazole, pyroxylone, carpropamide, diclocimet, phenoxanyl, etc.
Benzimidazole agents; benomyl, thiophanate methyl, thiabendazole and the like.
Dicarboximide agents; iprodione, procymidone, etc.
Carboxyanilide agents; oxycarboxin, mepronil, flutolanil, furametopyl, tifluzamide and the like.
Phenylamide-based agents; metalaxyl, oxadixyl and the like.
Sterol biosynthesis inhibitors; triadimephone, vitertanol, fenbuconazole, microbutanyl, hexaconazole, tebuconazole, propiconazole, difenoconazole, ipconazole, imibenconazole, cyproconazole, triflumizole, prochloraz, pefrazoate, oxpoconazole Fumarate, fenarimol, pyrifenox, triphorin, tetraconazole, cimeconazole, etc.
Strobilurins; azoxystrobin, cresoxime methyl, trifloxystrobin, metminostrobin, pyraclostrobin, orissastrobin, picoxystrobin, fluoxastrobin, etc.

Anilinopyrimidine agents; pyrimethanil, mepanipyrim, cyprodinil and the like.
Synthetic antibacterial agents; teclophthalam, oxolinic acid, etc.
Other synthetic disease control agents: probenazole, acibenzoral S methyl, isoprothiolane, ferrimzone, dichromedin, pencyclon, fluorimide, captan, dicloflurane, tolylfuranid, chlorothalonil, dithianon, quinomethionate, dinocap, dimethylolmol, diflumetrim, fludioxonil, benchazole Fluazinam, simoxanyl, famoxadone, iminotadine triacetate, iminoctadine albecylate, propamocarb hydrochloride, dimethomorph, cyazofamide, fenhexamide, dietofencarb, thiazinyl, benchavaricarb isopropyl, ethaboxam and the like.
Antibiotics: Blasticidin S, Kasugamycin, Polyoxin, Validamycin A, Streptomycin, Oxytetracycline, Mildiomycin, etc.
Natural products: machine oil, rapeseed oil, soybean lecithin, etc.
Biological agent: shiitake mycelium extract, live Trichoderma fungus, Agrobacterium radiobacter, non-pathogenic Erwinia carotobola subsposis, Bacillus subtilis, Talalomyces flavus, Pseudomonas fluorescens, Pseudomonas CAB-2, non-pathogenic Fusarium oxysporum, etc.
Soil disease control agent: fursulfamide, hydroxyisoxazole, echromezol, dazomet, chloroneb, metasulfocarb, methylisothiocyanate, DD, methyl bromide, chlorpicrin, carbam and the like.

(3-7-2) Pests and mite control agents Organophosphorus pest control agents: cyanophos, fenthion, fenitrothion, diclofenthion, pyrimifosmethyl, diazinon, quinalphos, isoxathione, pyridafenthion, chlorpyrifosmethyl, chlorpyrifos, bamidione, malathion, phentoate, dimethoate, Thiometone, disulfoton, hosalon, methidathione, prothiophos, sulprophos, profenophos, pyracrophos, dichlorvos, monocrotophos, nared, tetrachlorbinphos, dimethylvinphos, chlorfenvinphos, propaphos, acephate, isofenphos, trichlorfone, EPN, ethion and the like.
Carbamate pest control agents: carbaryl, isoprocarb, fenocarb, propoxur, XMC, ethiophencarb, pyrimicarb, bendiocarb, carbosulfan, benfuracarb, furthiocarb, mesomil, oxamyl, thiodicarb, alanib
Pyrethroid insecticides: aresulin, resmethrin, permethrin, cypermethrin, cyhalothrin, cyfluthrin, tralomethrin, fenpropatoline, bifenthrin, fenvalerate, flucitrinate, fulvalinate, acrinatrin, cycloprotorin, etofenprox, silafluophene, tefluthrin etc.
Nereistoxin pest control agents; cartap, thiocyclam, bensultap, etc.
Neonicotinoid pest control agents: imidacloprid, acetamiprid, nitenpyram, thiacloprid, thiamethoxam, clothianidin, dinotefuran and the like.
Insect growth control agents; buprofezin, isoprothiolane, diflubenzuron, teflubenzuron, hexaflumuurone, lufenuron, flufenoxuron, chlorfluazuron, tebufenozide, chromafenozide, cyromazine, etc.
Other synthetic pest control agents: benzoepin, fipronil, pymetrozine, chlorfenapyr, diafenthiuron, indoxacarb, emamectin benzoic acid, sodium oleate, potassium oleate, DBEDC, metaldehyde, adhesive, methoxyphenozide, tolfenpyrad, etc.
Natural pest control agents: pyrethrin, rotenone, nicotine, machine oil, rapeseed oil, soybean lecithin, starch, fatty acid glyceride, propylene glycol monofatty acid ester, diatomaceous earth, etc.

Mite control agent: Kelsen, phenisobromolate, tetradiphone, propargite, quinomethionate, amitraz, phenothiocarb, hexythiazox, fenbutatin oxide, dienochlor, fenpyroximate, tebufenpyrad, fluazinam, pyridaben, pyrimidifene, clofentezine, etoxazole, dinocap Prox, polynactin complex, milbemectin, bialaphos, acequinosyl, bifenazate, fluacripyrim, etc.
Nematode control agents: DD, DCIP, dazomet, benomyl, etoprofos, phostiazete, mesulfenfos, morantel tartrate, kazusafos, levamisole hydrochloride, nemadectin and the like.
Fumigant; methyl bromide, chloropicrin, carbam, carbam sodium salt, hydrocyanic acid, hydrogen phosphide, aluminum phosphide, ethylene oxide, carbon dioxide, methyl isothiocyanate, sulfuryl fluoride, etc.
Biological pest control agents: BT, Spinosad, Boberia Bronniati, Boberia Vasiana, Verticillium lecani, Steinerne capocapusae, Steinerne kushidai, Steinerne gracerai, Monacrosporium fimatopagum, Pasteur siromy pesomotrans , Natural enemies (Chile dust mite, Kukumeri sky dust mite, Colleman aura wasp, Onsitsu wasp, Sabakutsubachi wasp, Isaea Himebachi, Hamokogori bee, Shogama flies, etc.)

(3-7-3) Attractant Insect pheromone attractant: Little A, Beet Armor, Diamor, Peach Fluor, Tetradecenyl Acetate, Tortilla, Pyrimal, Arimal, Oriflua, Cheritor, Bullwell, Loucal, Fisylua, Ochimeric Norua, Sachimeric Norua , Sweetvillea, Fall web lure, etc.
Other attractants: Pinene oil, methyl eugenol, protein hydrolysates, culua, methyl phenyl acetate, etc.
Rodenticide; monofluoroacetate, coumatetralyl, warfarin, chlorofacinone, difacsinone, zinc phosphide, thallium sulfate, etc.
Other: Lime nitrogen etc.

(3-7-4) Herbicides Phenoxy herbicides; 2,4-PA, MCPA, MCPB, MCPP, triclopyr, cromeprop, naproanilide, phenoxapropethyl, cihalohopbutyl, fluazihop, quizalofopethyl and the like.
Carbamate herbicides: IPC, fenmedifam, desmedifam, beniocarb, orthobencarb, esprocarb, molinate, dimethylpiperate, pyributycarb, etc.
Acid amide herbicides: DCPA, alachlor, pretilachlor, metolachlor, butachlor, dimethenamide, tenyl chlor, bromobutide, etobenzanide, diflufenican, mefenacet, napropamide, fenfentrol, propyzamide, isoxaben, ashram and the like.
Urea-based herbicides: DCMU, linuron, ciduron, daimuron, cumylron, carbylate, isouron, tebuthiouron, etc.
Sulfonyl ureas: Bensulfuron methyl, ethoxysulfuron, pyrazosulfuron ethyl, azimusulfuron, halosulfuron methyl, frazasulfuron, synosulfuron, nicosulfuron, rimsulfuron, thifensulfuron methyl, imazosulfuron, metsulfuron methyl, cyclosulfam Ron etc.
Pyrimidyloxybenzoic acid herbicides; pyriminobac-methyl, bispyribac sodium salt, etc.
Triazine herbicides; CAT, atrazine, cimetrin, amethrin, promethrin, dimetamethrin, cyanazine, triadifram, metribudine, etc.
Diazine herbicides; for example, terbacil, bromacil, butaphenacyl, renacil, PAC, bentazone, pyridate and the like.

Diazole herbicides; pyrazolate, pyrazoxifene, benzophenap, pyraflufenethyl and the like.
Bipyridylium herbicides; paraquat, diquat, etc.
Dinitroaniline herbicides; trifluralin, vesulodin, prodiamine, pendimethalin, oryzalin, etc.
Aromatic carboxylic acid herbicides; MDBA, imazapyr, imazaquin, imazaquin ammonium salt, dithiopyr, TCTP, imazamox ammonium salt, fentolazamide and the like.
Aliphatic herbicides; pelargonic acid, DPA, tetrapion, etc.
Organophosphorus herbicides; piperophos, amiprophos methyl, butamifos, SAP, etc.
Amino acid herbicides: glyphosate isopropylamine salt, glyphosate ammonium salt, glyphosate trimesium salt, glyphosate potassium salt, bialaphos, glufosinate and the like.
Other organic herbicides: ioxinyl, biphenox, DBN, DCBN, cetoxidim, cretodim, tepraloxydim, CAN, indanophan, chlorphthalim, endartor disodium salt, benferate, flurosum, pentoxazone, oxadichrome mephone, carfentrazone ethyl, flumioxazin, Benzobicyclone, etc.
Inorganic herbicides; cyanate and the like.

(3-7-5) Addition amount of other drugs The above other drugs depend on the type of drug and the type of pest control agent applied, but each drug may exhibit the desired efficacy sufficiently. It is added in an amount that can. For example, the said other chemical | medical agent is 0.1-1000 mass% with respect to the mass of a pest control agent, Preferably, it adds in the quantity of 0.5-500 mass%.
EXAMPLES Hereinafter, although an Example, a formulation example, and a test example demonstrate this invention further in detail, this invention is not limited to these.

Examples of pyrimidine derivatives of the present invention are shown below.
The structures of the compounds in each table were confirmed by physical property values such as NMR, IR, MS, elemental analysis, and melting point. ¹ H-NMR and ¹⁹ F-NMR were measured using MERCURY 300 manufactured by Varian technologies Inc., and melting point (mp) was measured using MEL-TEMP. Manufactured by LABORATORY DEVICES INC.
In the NMR data, s is a singlet, d is a doublet, t is a triplet, q is a quartet, dd is a double doublet, dt is a double triplet, td is a triplet, m is a multiplet, and br is Means broad.
^{In 1} H-NMR, when CDCl ₃ was used as a solvent, CHCl ₃ = 7.26 ppm was used as an internal standard, and when DMSO-d ₆ was used, DMSO = 2.49 ppm was used as an internal standard. ^{In 19} F-NMR, C ₆ F ₆ = 0 ppm was used as an internal standard in any solvent.

<Example 1>
(1) Process (1) Route A
(1-1) Preparation of compound represented by formula [III]: Synthesis of 4-chloro-2- (pyridin-3-yl) -6-trifluoromethylpyrimidine
3-Cyanopyridine 36.0 g (346 mmol) was added to 28% sodium methoxide methanol solution 33.4 g (173 mmol), and the mixture was stirred at 25 ° C. overnight. Thereafter, 27.8 g (519 mmol) of ammonium chloride was further added, and the mixture was stirred at 25 ° C. overnight. The obtained reaction product was filtered, and the obtained filtrate was dried under reduced pressure, and then acetone was added to collect the deposited precipitate. The obtained precipitate was washed with acetone and dried to obtain 38.8 g (yield 71%) of nicotine amidine [ ¹ H-NMR (DMSO-d ₆ ): δ7.60 (dd, 1 H), 8.24 ( dt, 1 H), 8.81 (dd, 1 H), 9.01 (d, 1 H)].
38.8 g (246 mmol) of the above nicotine amidine was added to 33.7 ml (246 mmol) of ethyl 4,4,4-trifluoromethylacetoacetate in 83.7 g (246 mmol) of a 20% sodium ethoxide ethanol solution, and the mixture was stirred at 25 ° C. for 15 minutes. In addition to what was stirred, 26.6 g (492 mmol) of sodium methoxide was added, and it recirculate | refluxed for 16 hours. The obtained reaction product was filtered, the obtained filtrate was distilled off, the residue was diluted with water, acidified with hydrochloric acid, and the deposited precipitate was collected by filtration. The obtained precipitate was washed with water and dried to obtain 40.5 g of 4-hydroxy-2- (pyridin-3-yl) -6-trifluoromethylpyrimidine (yield 70%) [ ¹ H-NMR ( DMSO-d ₆ ): δ6.95 (s, 1 H), 7.59 (dd, 1 H), 8.44 (dt, 1 H), 8.86 (dd, 1 H), 9.22 (d, 1 H), 13.5 ( br, 1 H), ¹⁹ F-NMR (DMSO-d ₆ ): δ92.136 (s)].
4-hydroxy-2- (pyridin-3-yl) -6-trifluoromethylpyrimidine obtained above (40.5 g (168 mmol)) and phosphoryl chloride (125 ml, 1344 mmol) added dropwise with 8 drops of dimethylaniline And refluxed for 3 hours. The reaction was dropped into ice water and neutralized with aqueous sodium hydroxide. The deposited precipitate is collected by filtration, and the resulting precipitate is washed with water to give 4-chloro-2- (pyridin-3-yl) -6-trifluoromethylpyrimidine (a compound represented by the formula [III]). Obtained [ ¹ H-NMR (CDCl ₃ ): δ 7.46 (dd, 1 H), 7.61 (s, 1 H), 8.74 (dt, 1 H), 8.79 (dd, 1 H), 9.67 (d, 1 H), ¹⁹ F-NMR (CDCl ₃ ): δ91.275 (s)].

(1-2) Preparation of a compound represented by the formula [VII]: Synthesis of 4- (2-methoxybenzylthio) -2- (pyridin-3-yl) -6-trifluoromethylpyrimidine As described above The obtained 4-chloro-2- (pyridin-3-yl) -6-trifluoromethylpyrimidine (1.43 g, 5.5 mmol) was dissolved in dimethylformamide, and 2-methoxybenzyl mercaptan (formula [IV]) 0.85 g ( 5.5 mmol) and 0.84 g (6.1 mmol) of potassium carbonate were added, and the mixture was stirred at 25 ° C. for 20 hours. Water was added to the resulting reaction product, which was filtered and dried to obtain 4- (2-methoxybenzylthio) -2- (pyridin-4-yl) -6-trifluoromethylpyrimidine [ ¹ H-NMR. (CDCl ₃ ): δ3.90 (s, 3 H), 4.65 (s, 2 H), 6.90 (m, 2 H), 7.27 (t, 1 H), 7.37 (s, 1 H), 7.39-7.47 (m, 2 H), 8.75-8.77 (m, 2 H), 9.71 (s, 1 H), ¹⁹ F-NMR (CDCl ₃ ): δ90.908 (s)].

(2) Process (1) Route B
(2-1) Preparation of compound represented by formula [V]: Synthesis of 4-mercapto-2- (pyridin-3-yl) -6-trifluoromethylpyrimidine 4 obtained in (1-1) above -Chloro-2- (pyridin-3-yl) -6-trifluoromethylpyrimidine (2.60 g, 10 mmol) was dissolved in ethanol, 0.76 g (10 mmol) of thiourea was added, and the mixture was refluxed for 18 hours. After distilling off ethanol, the reaction mixture was diluted with water, and 1.2 g (30 mmol) of an aqueous solution of sodium hydroxide was added dropwise with aeration of nitrogen under ice cooling, followed by stirring at 25 ° C. overnight. It was made weakly acidic with dilute hydrochloric acid, and the deposited precipitate was collected by filtration and dried to obtain 1.03 g (yield 40%) of 4-mercapto-2- (pyridin-3-yl) -6-trifluoromethylpyrimidine [ ¹ H-NMR (CDCl ₃ ): δ 7.44 (dd, 1H), 8.05 (s, 1H), 8.67 (dt, 1H), 8.78 (dd, 1H), 9.62 (d, 1H). ¹⁹ F-NMR ( CDCl ₃ ): δ92.646 (s)].
(2-2) Preparation of the compound represented by the formula [VII]: Synthesis of 4- (2-methoxybenzylthio) -2- (pyridin-3-yl) -6-trifluoromethylpyrimidine As described above The resulting 4-mercapto-2- (pyridin-3-yl) -6-trifluoromethylpyrimidine (1.03 g, 4 mmol) was dissolved in dimethylformamide, and 2-methoxybenzyl chloride (0.62 g, 4 mmol) and potassium carbonate (0.61 g) were dissolved. (4.4 mmol) was added and stirred at 25 ° C. for 20 hours. Water was added to the resulting reaction product, which was filtered and dried to obtain 4- (2-methoxybenzylthio) -2- (pyridin-3-yl) -6-trifluoromethylpyrimidine [ ¹ H-NMR. (CDCl ₃ ): δ3.90 (s, 3 H), 4.65 (s, 2 H), 6.90 (m, 2 H), 7.27 (t, 1 H), 7.37 (s, 1 H), 7.39-7.47 (m, 2 H), 8.75-8.77 (m, 2 H), 9.71 (s, 1 H), ¹⁹ F-NMR (CDCl ₃ ): δ90.908 (s)].

(3) Process (2)
Preparation of compounds of formula [I]: 4- (2-methoxybenzylsulfonyl) -2- (pyridin-3-yl) -6-trifluoromethylpyrimidine and 4- (2-methoxybenzylsulfinyl) -2 Synthesis of 2- (pyridin-3-yl) -6-trifluoromethylpyrimidine 4- (2-methoxybenzylthio) -2- (pyridin-3-yl) -6-trifluoromethyl obtained as described above 0.98 g (2.6 mmol) of pyrimidine was dissolved in acetic acid, 0.17 g (0.52 mmol) of sodium tungstate dihydrate was added, 0.59 g (5.2 mmol) of 30% aqueous hydrogen peroxide was added dropwise, and the mixture was added at 25 ° C. Stir overnight. Water was added to the obtained reaction product and filtered, and the resulting crude product was purified by column chromatography (hexane: ethyl acetate = 10: 1 elution) to give 4- (2-methoxybenzylsulfonyl) -2- (Pyridin-3-yl) -6-trifluoromethylpyrimidine (Table 1-35) 0.41 g (39% yield) and 4- (2-methoxybenzylsulfinyl) -2- (pyridin-3-yl) -6 -Trifluoromethylpyrimidine (Table 2-19) 0.14 g (14% yield) was obtained.

・ NMR data of 4- (2-methoxybenzylsulfonyl) -2- (pyridin-3-yl) -6-trifluoromethylpyrimidine
¹ H-NMR (CDCl ₃ ): δ 3.43 (s, 3 H), 4.83 (s, 1 H), 6.71 (d, 1 H), 6.97 (t, 1 H), 7.27 (d, 1 H), 7.35 (t, 1 H), 7.51 (dd, 1 H), 7.94 (s, 1 H), 8.76 (dt, 1 H), 8.84 (d, 1 H), 9.70 (s, 1 H), δ ¹⁹ F-NMR (DMSO-d ₆ ): δ91.403 (s)
・ NMR data of 4- (2-methoxybenzylsulfinyl) -2- (pyridin-3-yl) -6-trifluoromethylpyrimidine
¹ H-NMR (DMSO-d ₆ ): δ3.47 (s, 3 H), 4.43 (q, 2 H), 6.73 (d, 1 H), 6.96 (t, 1 H), 7.19 (d, 1 H), 7.32 (t, 1 H), 7.49 (dd, 1 H), 7.94 (s, 1 H), 8.71 (dt, 1 H), 8.81 (dd, 1 H), 9.61 (s, 1 H) , δ ¹⁹ F-NMR (DMSO-d ₆ ): δ91.250 (s)

<Example 2>
(1) Preparation of compound represented by formula [III]: Synthesis of 4-chloro-2- (pyridin-4-yl) -6-trifluoromethylpyrimidine
4-Cyanopyridine 25.0 g (240 mmol) was added to 28% sodium methoxide methanol solution 23.2 g (120 mmol), and the mixture was stirred at 25 ° C. overnight. Thereafter, 19.3 g (360 mmol) of ammonium chloride was further added, and the mixture was stirred at 25 ° C. overnight. The obtained reaction product was filtered, and the obtained filtrate was dried under reduced pressure, and then acetone was added and the deposited precipitate was collected by filtration. The obtained precipitate was washed with acetone and dried to obtain 27.0 g (93% yield) of isonicotimamidine [ ¹ H-NMR (DMSO-d ₆ ): δ3-4 (br, 2 H), 7.34 (d, 2 H), 8.84 (d, 2 H), 9.0-9.5 (br, 1 H)].
Separately, 32.7 ml (222 mmol) of ethyl 4,4,4-trifluoromethylacetoacetate was added to 75.5 g (222 mmol) of a 20% sodium ethoxide ethanol solution and stirred at 25 ° C. for 15 minutes. To the obtained solution, 27.0 g (222 mmol) of isonicotine amidine obtained above and 12.0 g (222 mmol) of sodium methoxide were added and refluxed for 16 hours. The obtained reaction product was filtered, the obtained filtrate was distilled off, the residue was diluted with water, acidified with hydrochloric acid, and the deposited precipitate was collected by filtration. The obtained precipitate was washed with water and dried to obtain 34.2 g (yield 64%) of 4-hydroxy-2- (pyridin-4-yl) -6-trifluoromethylpyrimidine [ ¹ H-NMR ( DMSO-d ₆ ): δ7.01 (s, 1 H), 8.04 (d, 2 H), 8.79 (d, 2 H), 12-13 (br, 1 H), ¹⁹ F-NMR (DMSO-d ₆ ): δ92.756 (s)].
4-hydroxy-2- (pyridin-4-yl) -6-trifluoromethylpyrimidine obtained above (2.41 g (10 mmol)) and phosphoryl chloride (7.5 ml, 80 mmol) in 5 drops of dimethylaniline And refluxed for 3 hours. The reaction was added dropwise to ice water and neutralized with aqueous sodium hydroxide. The deposited precipitate was collected by filtration, and the resulting precipitate was washed with water to give 4-chloro-2- (pyridin-4-yl) -6-trifluoromethylpyrimidine (a compound represented by the formula [III]) 1.66 g (yield 64%) was obtained [ ¹ H-NMR (CDCl ₃ ): δ7.67 (s, 1 H), 8.33 (d, 2 H), 8.84 (d, 2 H), ¹⁹ F-NMR (CDCl ₃ ): δ91.366 (s)].
(2) Preparation of the compound represented by the formula [VII] (Step (1) Route A): Synthesis of 4-benzylthio-2- (pyridin-4-yl) -6-trifluoromethylpyrimidine As described above The obtained 4-chloro-2- (pyridin-4-yl) -6-trifluoromethylpyrimidine (1.25 g, 4.8 mmol) was dissolved in dimethylformamide, and benzyl mercaptan (formula [IV]) 0.56 ml (4.8 mmol) And 0.66 g (4.8 mmol) of potassium carbonate were added, and the mixture was stirred at 25 ° C. for 20 hours. Water was added to the obtained reaction product, followed by filtration and drying to obtain 4-benzylthio-2- (pyridin-4-yl) -6-trifluoromethylpyrimidine (yield 95%) [ ¹ H-NMR (CDCl ₃ ): δ4.64 (s, 2 H), 7.26-7.43 (m, 5 H), 7.45 (s, 1 H), 8.30 (d, 2 H), 8.81 (d, 2 H), ¹⁹ F-NMR (CDCl ₃ ): δ91.030 (s)].

(3) Preparation of compound represented by formula [I] (step (2)): Synthesis of 4- (benzylsulfonyl) -2- (pyridin-4-yl) -6-trifluoromethylpyrimidine As described above. 4-benzylthio-2- (pyridin-4-yl) -6-trifluoromethylpyrimidine (1.67 g, 4.8 mmol) obtained in the above was dissolved in acetic acid, and sodium tungstate dihydrate (0.32 g, 0.96 mmol) was dissolved. In addition, 1.09 g (9.6 mmol) of 30% aqueous hydrogen peroxide was added dropwise and stirred overnight at 25 ° C. Water was added to the resulting reaction product and filtered, and the resulting crude product was purified by column chromatography (elution with hexane: ethyl acetate = 5: 1) to give 4- (benzylsulfonyl) -2- (pyridine- 4-yl) -6-trifluoromethylpyrimidine (1.7 g, yield 92%) was obtained (Table 1-121) [ ¹ H-NMR (DMSO-d ₆ ): δ5.11 (s, 2 H), 7.53 (s, 5 H), 8.33 (d, 1 H), 8.38 (d, 1 H), 8.90 (s, 1 H), ¹⁹ F-NMR (DMSO-d ₆ ): δ92.86 (s)] .

<Example 3>
(1) Preparation of a compound represented by the formula [VII] (Step (1) Route A): 4- (2-methoxybenzylthio) -2- (pyridin-4-yl) -6-trifluoromethylpyrimidine Composition
4-Chloro-2- (pyridin-4-yl) -6-trifluoromethylpyrimidine was synthesized in the same manner as in Example 2.
Dissolve 3.0 g (11.5 mmol) of 4-chloro-2- (pyridin-4-yl) -6-trifluoromethylpyrimidine in dimethylformamide and add 1.78 g (11.5 mmol) of 2-methoxybenzyl mercaptan (formula [IV]) And 1.75 g (12.7 mmol) of potassium carbonate were added, and the mixture was stirred at room temperature for 20 hours. Water was added to the resulting reaction product, filtered and dried, and 4.10 g of 4- (2-methoxybenzylthio) -2- (pyridin-4-yl) -6-trifluoromethylpyrimidine (yield 94%) ) Obtained [ ¹ H-NMR (CDCl ₃ ): δ 3.90 (s, 3 H), 4.66 (s, 2 H), 6.87-6.93 (m, 2 H), 7.28 (t, 1 H), 7.41 (d, 1 H), 7.43 (s, 1 H), 8.35 (d, 2 H), 8.82 (d, 2 H), ¹⁹ F-NMR (CDCl ₃ ): δ92.927 (s)

(2) Preparation of compound represented by formula [I] (step (2)): Synthesis of 4- (2-methoxybenzylsulfonyl) -2- (pyridin-4-yl) -6-trifluoromethylpyrimidine 4- (2-methoxybenzylthio) -2- (pyridin-4-yl) -6-trifluoromethylpyrimidine (4.09 g, 10.8 mmol) obtained as described above was dissolved in acetic acid, 0.70 g (2.16 mmol) of the Japanese product was added, and 2.40 g (21.6 mmol) of 30% aqueous hydrogen peroxide was added dropwise, followed by stirring at 25 ° C. overnight. Water was added to the resulting reaction product and filtered, and the resulting crude product was purified by column chromatography (elution with hexane: ethyl acetate = 5: 1) to give 4- (2-methoxybenzylsulfonyl) -2- 1.86 g (42% yield) of (pyridin-4-yl) -6-trifluoromethylpyrimidine was obtained (Table 1-155) [ ¹ H-NMR (CDCl ₃ ): δ3.39 (s, 3 H) , 4.82 (s, 2 H), 6.70 (d, 1 H), 6.98 (t, 1 H), 7.29-7.38 (m, 2 H), 7.98 (s, 1 H), 8.34 (d, 2 H) , 8.88 (d, 2 H), δ ¹⁹ F-NMR (CDCl ₃ ): δ 92.927 (s)].

<Example 4>
(1) Preparation of compound represented by formula [III]: Synthesis of 4-chloro-2- (2-methylpyridin-4-yl) -6-trifluoromethylpyrimidine
To 28.0 g (257 mmol) of 2-picoline N-oxide was added 26.8 ml (283 mmol) of dimethyl sulfate in an ice bath, and the mixture was stirred at 25 ° C. for 18 hours. Then, it diluted with water and chloroform extraction was performed. Purification by column chromatography (hexane: ethyl acetate = 5: 1 elution) yielded 10.4 g (yield 38%) of 4-cyano-2-methylpyridine [ ¹ H-NMR (CDCl ₃ ): δ2.63 ( s, 3 H), 7.33 (dd, 1 H), 7.39 (d, 1 H), 8.67 (dd, 1 H)].
19.2 g (162 mmol) of 4-cyano-2-methylpyridine obtained as described above was added to 15.7 g (81 mmol) of 28% sodium methoxide methanol solution, and the mixture was stirred at 25 ° C. overnight. Thereafter, 13.0 g (244 mmol) of ammonium chloride was further added, followed by stirring at 25 ° C. overnight. The obtained reaction product was filtered, and the obtained filtrate was dried under reduced pressure, and then acetone was added and the deposited precipitate was collected by filtration. The obtained precipitate was washed with acetone and dried to obtain 13.8 g of 2-methylisonicotinamidine (yield 63%) [ ¹ H-NMR (CDCl ₃ ): δ2.54 (s, 3 H), 2.5-3.2 (br, 2 H), 7.29 (dd, 1 H), 7.51 (d, 1 H), 8.58 (dd, 1 H), 9-10 (br, 1 H)].

Separately, 15.0 ml (102 mmol) of ethyl 4,4,4-trifluoromethylacetoacetate was added to 34.7 g (102 mmol) of 20% sodium ethoxide ethanol solution and stirred at room temperature for 15 minutes. To the obtained solution, 13.8 g (102 mmol) of 2-methylisonicotinamidine obtained above and 5.51 g (102 mmol) of sodium methoxide were added and refluxed for 15 hours. The obtained reaction product was filtered, the obtained filtrate was distilled off, the residue was diluted with water, acidified with hydrochloric acid, and the deposited precipitate was collected by filtration. The obtained precipitate was washed with water and dried to obtain 16.6 g (yield 64%) of 4-hydroxy-2- (2-methylpyridin-4-yl) -6-trifluoromethylpyrimidine [ ¹ H -NMR (CDCl ₃ ): δ2.56 (s, 3 H), 6.97 (s, 1 H), 7.83 (dd, 1 H), 7.90 (d, 1 H), 8.63 (dd, 1 H), ¹⁹ F-NMR (CDCl ₃ ): δ92.178 (s)].
4-Hydroxy-2- (2-methylpyridin-4-yl) -6-trifluoromethylpyrimidine (16.6 g, 65 mmol) obtained above was added to phosphoryl chloride 48.5 ml (520 mmol) and dimethylaniline 10 ml ( 78 mmol) was added dropwise, and the mixture was refluxed for 3 hours. The reaction was dropped into ice water and neutralized with aqueous sodium hydroxide. The deposited precipitate is collected by filtration, and the resulting precipitate is washed with water to give 4-chloro-2- (2-methylpyridin-4-yl) -6-trifluoromethylpyrimidine (represented by the formula [III] Compound) 8.4 g (yield 72%) was obtained [ ¹ H-NMR (CDCl ₃ ): δ 2.69 (s, 3 H), 7.66 (s, 1 H), 8.11 (dd, 1 H), 8.18 (d, 1 H), 8.70 (dd, 1 H), ¹⁹ F-NMR (CDCl ₃ ): δ91.373 (s)].

(2) Preparation of compound represented by formula [VII] (Step (1) Route A): Synthesis of 4-phenylethylthio-2- (2-methylpyridin-4-yl) -6-trifluoromethylpyrimidine 4-Chloro-2- (2-methylpyridin-4-yl) -6-trifluoromethylpyrimidine 1.09 g (4.0 mmol) obtained as described above was dissolved in dimethylformamide, and phenylethyl mercaptan (formula [ IV]) 0.54 ml (4.0 mmol) and 0.61 g (4.4 mmol) of potassium carbonate were added and stirred at 25 ° C. for 20 hours. Water was added to the obtained reaction product, followed by filtration and drying to obtain 4-phenylethylthio-2- (2-methylpyridin-4-yl) -6-trifluoromethylpyrimidine [ ¹ H-NMR ( CDCl ₃ ): δ2.68 (s, 3 H), 3.12 (dd, 2 H), 3.61 (dd, 2 H), 7.26-7.42 (m, 5 H), 7.42 (s, 1 H), 8.11 ( dd, 1 H), 8.18 (d, 1 H), 8.67 (dd, 1 H), ¹⁹ F-NMR (CDCl ₃ ): δ91.055 (s)].

(3) Preparation of compound represented by formula [I] (step (2)): Synthesis of 4- (phenylethylsulfinyl) -2- (2-methylpyridin-4-yl) -6-trifluoromethylpyrimidine 1.5 g (4.0 mmol) of 4-phenylethylthio-2- (2-methylpyridin-4-yl) -6-trifluoromethylpyrimidine obtained as described above was dissolved in acetic acid-dimethylformamide, and tungstic acid was dissolved. Sodium dihydrate 0.13 g (0.4 mmol) was added, 0.91 g (8.0 mmol) of 30% aqueous hydrogen peroxide was added dropwise, and the mixture was stirred at 25 ° C. overnight. Water was added to the resulting reaction product and filtered, and the resulting crude product was purified by column chromatography (elution with hexane: ethyl acetate = 5: 1) to give 4- (benzylsulfonyl) -2- (2- Methylpyridin-4-yl) -6-trifluoromethylpyrimidine (0.3 g, 17% yield) was obtained (Table 2-60) [ ¹ H-NMR (CDCl ₃ ): δ2.08 (s, 3 H) , 3.16 (m, 2 H), 3.55 (m, 2 H), 7.16 (s, 5 H), 8.06 (d, 1H), 8.13 (s, 1 H), 8.19 (s, 1H), 8.71 (d , 1 H), ¹⁹ F-NMR (CDCl ₃ ): δ91.525 (s)].

(4) Preparation of compound represented by formula [I] (step (2)): Synthesis of 4- (phenylethylsulfonyl) -2- (2-methylpyridin-4-yl) -6-trifluoromethylpyrimidine 1.5 g (4.0 mmol) of 4-phenylethylthio-2- (2-methylpyridin-4-yl) -6-trifluoromethylpyrimidine obtained as described above was dissolved in acetic acid-dimethylformamide, and tungstic acid was dissolved. Sodium dihydrate 0.13 g (0.4 mmol) was added, 30% aqueous hydrogen peroxide 0.91 g (8.0 mmol) was added dropwise, and the mixture was stirred at 25 ° C. overnight. Water was added to the resulting reaction product and filtered, and the resulting crude product was purified by column chromatography (elution with hexane: ethyl acetate = 5: 1) to give 4- (benzylsulfonyl) -2- (2- Methylpyridin-4-yl) -6-trifluoromethylpyrimidine (0.7 g, yield 43%) was obtained (Table 2-61) [ ¹ H-NMR (CDCl ₃ ): δ2.72 (s, 3 H) , 3.21 (t, 2 H), 3.94 (t, 2 H), 7.07 (s, 5 H), 8.02 (s, 1 H), 8.07 (d, 1 H), 8.13 (s, 1 H), 8.74 (d, 1 H), ¹⁹ F-NMR (CDCl ₃ ): δ91.482 (s)].

<Example 5>
(3) Synthesis of 4-chloro-2- (pyrimidin-2-yl) -6-trifluoromethylpyrimidine
To 13.8 g (71 mmol) of 28% sodium methoxide methanol solution was added 15.0 g (142 mmol) of 2-cyanopyrimidine, and the mixture was stirred overnight at 25 ° C. Thereafter, 11.4 g (213 mmol) of ammonium chloride was further added, and the mixture was stirred at 25 ° C. overnight. The obtained reaction product was filtered, and the obtained filtrate was dried under reduced pressure, and then acetone was added and the deposited precipitate was collected by filtration. The obtained precipitate was washed with acetone and dried to obtain 16.5 g of pyrimidine-2-carboamidine hydrochloride (yield 73%) [ ¹ H-NMR (DMSO-d ₆ ): δ7.91 (t, 1H), 8.99 (br), 9.13 (d, 2H)].
Separately, 15.4 ml (104 mmol) of ethyl 4,4,4-trifluoromethylacetoacetate was added to 35.4 g (104 mmol) of a 20% sodium ethoxide ethanol solution and stirred at room temperature for 15 minutes. To the obtained solution, 16.5 g (104 mmol) of pyrimidine-2-carboamidine hydrochloride obtained above and 5.60 g (104 mmol) of sodium methoxide were added and refluxed for 16 hours. The obtained reaction product was filtered, the obtained filtrate was distilled off, the residue was diluted with water, acidified with hydrochloric acid, and the deposited precipitate was collected by filtration. The obtained precipitate was washed with water and dried to obtain 9.30 g (yield 66%) of 4-hydroxy-2- (pyrimidin-2-yl) -6-trifluoromethylpyrimidine [ ¹ H-NMR ( DMSO-d ₆ ): δ7.04 (s, 1 H), 7.76 (t, 1 H), 9.06 (d, 2 H), 13.2 (br, 1 H), ¹⁹ F-NMR (DMSO-d ₆ ) : δ92.677].

4-hydroxy-2- (pyrimidin-2-yl) -6-trifluoromethylpyrimidine (9.0 g, 37.1 mmol) obtained as described above was added dropwise to 30 ml (327 mmol) of phosphoryl chloride and 6 ml of dimethylaniline. The mixture was refluxed for 3 hours. The reaction was dropped into ice water and neutralized with aqueous sodium hydroxide. The deposited precipitate was collected by filtration, and the resulting precipitate was washed with water to give 4-chloro-2- (pyrimidin-2-yl) -6-trifluoromethylpyrimidine (a compound represented by the formula [III]) 8.10 g (84% yield) was obtained [ ¹ H-NMR (CDCl ₃ ): δ 7.47 (t, 1 H), 7.79 (s, 1 H), 9.02 (d, 1 H), ¹⁹ F-NMR (CDCl ₃ ): δ93.324].

(2) Preparation of the compound represented by the formula [VII] (Step (1) Route A): Synthesis of 4-benzylthio-2- (pyrimidin-2-yl) -6-trifluoromethylpyrimidine As described above The resulting 4-chloro-2- (pyrimidin-2-yl) -6-trifluoromethylpyrimidine (1.50 g, 5.8 mmol) was dissolved in dimethylformamide, 0.71 g (5.8 mmol) of benzyl mercaptan and 0.88 g of potassium carbonate ( 6.3 mmol) was added and stirred at 25 ° C. for 20 hours. Water was added to the resulting reaction product, which was filtered and dried to obtain 1.90 g (yield 95%) of 4-benzylthio-2- (pyrimidin-2-yl) -6-trifluoromethylpyrimidine. [ ¹ H-NMR (CDCl ₃ ): δ4.64 (s, 2 H), 7.24-7.32 (m, 3 H), 7.47 (t, 1 H), 7.50-7.53 (m, 2 H), 7.54 ( s, 1 H), 9.05 (d, 2 H), ¹⁹ F-NMR (CDCl ₃ ): δ93.080 (s)].

(3) Preparation of compound represented by formula [I] (step (2)): Synthesis of 4-benzylsulfonyl-2- (pyrimidin-2-yl) -6-trifluoromethylpyrimidine 4-Benzylthio-2- (pyrimidin-2-yl) -6-trifluoromethylpyrimidine 1.60 g (4.6 mmol) was dissolved in acetic acid, 0.30 g (0.92 mmol) of sodium tungstate dihydrate was added, 30% hydrogen peroxide solution 1.04 g (9.2 mmol) was added dropwise, and the mixture was stirred at 25 ° C. overnight. Water was added to the obtained reaction product and filtered, and the resulting crude product was purified by column chromatography (elution with hexane: ethyl acetate = 5: 1) to give 4- (benzylsulfonyl) -2- (pyrimidine- 2-yl) -6-trifluoromethylpyrimidine (1.07 g, yield 63%) was obtained (Table 2-65) [ ¹ H-NMR (CDCl ₃ ): δ4.91 (s, 2 H), 7.25- 7.37 (m, 5 H), 7.56 (t, 1 H), 8.14 (s, 1 H), 9.13 (d, 2 H), ¹⁹ F-NMR (CDCl ₃ ): δ93.403 (s)].

<Example 6>
(1) Preparation of compound represented by formula [III]: Synthesis of 4-chloro-2- (pyrazin-2-yl) -6-trifluoromethylpyrimidine
2-Cyanopyrazine (25.0 g, 238 mmol) was added to 28% sodium methoxide methanol solution (22.9 g, 119 mmol), and the mixture was stirred at 25 ° C overnight. Thereafter, 19.0 g (357 mmol) of ammonium chloride was further added, and the mixture was stirred at 25 ° C. overnight. The obtained reaction product was filtered, and the obtained filtrate was dried under reduced pressure, and then acetone was added and the deposited precipitate was collected by filtration. The obtained precipitate was washed with acetone and dried to obtain 33.8 g (yield 90%) of pyrazine-2-carbomidine hydrochloride [ ¹ H-NMR (DMSO-d ₆ ): δ7.0-9.0 ( br, 2 H), 8.90 (d, 1 H), 9.01 (d, 1 H), 9.61 (s, 1 H), 9.20-10.5 (br, 2 H)].
Separately, 31.4 ml (213 mmol) of ethyl 4,4,4-trifluoromethylacetoacetate was added to 72.5 g (213 mmol) of a 20% sodium ethoxide ethanol solution and stirred at room temperature for 15 minutes. To the obtained solution, 33.8 g (213 mmol) of pyrazine-2-carboamidine hydrochloride obtained above and 11.5 g (213 mmol) of sodium methoxide were added and refluxed for 16 hours. The obtained reaction product was filtered, the obtained filtrate was distilled off, the residue was diluted with water, acidified with hydrochloric acid, and the deposited precipitate was collected by filtration. The obtained precipitate was washed with water and dried to obtain 39.4 g (yield 77%) of 4-hydroxy-2- (pyrazin-2-yl) -6-trifluoromethylpyrimidine [ ¹ H-NMR ( DMSO-d ₆ ): δ7.02 (s, 1 H), 8.84 (dd, 1 H), 8.91 (d, 1 H), 9.39 (d, 1 H), 13.6 (br, 1 H), ¹⁹ F -NMR (DMSO-d ₆ ): δ92.404 (s)].

10.0 g (41.3 mmol) of 4-hydroxy-2- (pyrazin-2-yl) -6-trifluoromethylpyrimidine obtained as described above was added dropwise to 30 ml (327 mmol) of phosphoryl chloride and 6 ml of dimethylaniline. The mixture was refluxed for 3 hours. The reaction was dropped into ice water and neutralized with aqueous sodium hydroxide. The deposited precipitate was collected by filtration, and the obtained precipitate was washed with water to give 4-chloro-2- (pyrazin-2-yl) -6-trifluoromethylpyrimidine (a compound represented by the formula [III]) 7.49 g (yield 70%) was obtained [ ¹ H-NMR (CDCl ₃ ): δ 7.75 (s, 1 H), 8.77 (d, 1 H), 8.84 (dd, 1 H), 9.74 (d, 1 H), ¹⁹ F-NMR (CDCl ₃ ): δ92.982 (s)].

(2) Preparation of compound represented by formula [VII] (step (1) route A): Synthesis of 4-benzylthio-2- (pyrazin-2-yl) -6-trifluoromethylpyrimidine As described above The obtained 4-chloro-2- (pyrazin-2-yl) -6-trifluoromethylpyrimidine 1.50 g (5.8 mmol) was dissolved in dimethylformamide, and 0.71 g (5.8 mmol) of benzyl mercaptan (formula [IV]) was dissolved. And 0.88 g (6.3 mmol) of potassium carbonate were added, and the mixture was stirred at 25 ° C. for 20 hours. Water was added to the obtained reaction product, followed by filtration and drying to obtain 1.90 g (yield 95%) of 4-benzylthio-2- (pyrazin-2-yl) -6-trifluoromethylpyrimidine [ ¹ H -NMR (CDCl ₃ ): δ4.63 (s, 2 H), 7.26-7.35 (m, 3 H), 7.46-7.48 (m, 2 H), 7.50 (s, 1 H), 8.73 (d, 1 H), 8.84 (dd, 1 H), 9.68 (d, 1 H), ¹⁹ F-NMR (CDCl ₃ ): δ92.793 (s)].

(3) Preparation of compound represented by formula [I] (step (2)): Synthesis of 4-benzylsulfonyl-2- (pyrazin-2-yl) -6-trifluoromethylpyrimidine The obtained 4-benzylthio-2- (pyrazin-2-yl) -6-trifluoromethylpyrimidine 1.56 g (4.5 mmol) was dissolved in acetic acid, and sodium tungstate dihydrate 0.29 g (0.90 mmol) was added, 1.00 g (9.0 mmol) of 30% aqueous hydrogen peroxide was added dropwise. Stir at 25 ° C. overnight. Water was added to the resulting reaction product and filtered, and the resulting crude product was purified by column chromatography (elution with hexane: ethyl acetate = 5: 1) to give 4- (benzylsulfonyl) -2- (pyrazine- 2-yl) -6-trifluoromethylpyrimidine (0.85 g, yield 50%) was obtained (Table 2-70) [ ¹ H-NMR (CDCl ₃ ): δ4.86 (s, 2 H), 7.25- 7.35 (m, 5 H), 8.09 (s, 1 H), 8.84 (d, 1 H), 8.92 (dd, 1 H), 9.78 (d, 1 H), ¹⁹ F-NMR (CDCl ₃ ): δ93 .122 (s)].

  The compounds shown in Tables 1 to 3 can be synthesized in the same manner as in Examples 1 to 6.

<Formulation example>
Next, formulation examples of the pest control agent of the present invention are shown. In addition, a part represents a mass part when the mass of the preparation is 100 parts by mass.
Formulation Example 1 Hydrating Agent 50 parts of the pyrimidine derivative obtained in the above Examples 1 to 6 finely pulverized with a hammer mill, 3 parts of sodium lignin sulfonate, 2 parts of sodium lauryl sulfate, and synthetic hydrous silica 10 Then, 35 parts of clay and 35 parts of clay were mixed well, and then pulverized by a jet mill to obtain each wettable powder.

Formulation Example 2 Emulsion 10 parts of the pyrimidine derivative obtained in Examples 1 to 6, 9 parts of polyoxyethylene styrenated phenyl ether, 6 parts of calcium dodecylbenzenesulfonate, 20 parts of N-methylpyrrolidone and 55 parts of xylene are uniformly mixed. Each emulsion was obtained by dissolution.

Formulation Example 3 Granules 5 parts of the pyrimidine derivative obtained in the above Examples 1-6 finely pulverized with a hammer mill to 3 parts of sodium lignin sulfonate, 1 part of sodium dodecylbenzenesulfonate, 30 parts of bentonite After adding 61 parts of clay and thoroughly mixing with stirring, an appropriate amount of water is added to the mixture, and the mixture is further kneaded, granulated with an extrusion granulator, air-dried, sized and sieved to obtain each granule. An agent was obtained.

Formulation Example 4 Powder 1 part of the pyrimidine derivative obtained in Examples 1-6, 5 parts of synthetic hydrous silicate fine powder, 0.3 part of PAP, and 93.7 parts of clay were finely pulverized with a hammer mill to an average particle size of 8 μm. In addition, each powder was obtained by stirring and mixing with a pin mill.

Formulation Example 5 Flowable agent 10 parts of the pyrimidine derivative obtained in Examples 1 to 6 finely pulverized with a hammer mill, 3 parts of polyoxyethylene styrene styrenated phenyl ether phosphate ammonium salt, silicon antifoam 1 part of the agent and 36 parts of water were added and stirred with a mixer to obtain a dispersion. This dispersion was finely pulverized to an average particle size of 1.5 μm by a bead mill, and then 40 parts of an aqueous solution containing 0.5 part of xanthan gum and 0.2 part of preservative was added thereto, and 10 parts of propylene glycol was further added. Were mixed with stirring to obtain each 10% flowable agent.

<Effectiveness test example>
Next, test examples show that the pyrimidine derivative of the present invention or a salt thereof is useful as an active ingredient of a pest control agent. In addition, the pyrimidine derivative or its salt of this invention is shown with the compound number of Tables 1-3, and the compound used for the comparison control is shown with the following compound symbol.
Compound A: 6-benzylsulfonyl-2-methyl-4-trifluoromethylpyrimidine
(Compound described in JP-A-2001-247411)
Compound B: 6-Benzylsulfonyl-2-phenyl-4-trifluoromethylpyrimidine
(Compound described in JP-A-2001-247411)
Compound C: 4-methyl-6-methylsulfonyl-2- (pyridin-4-yl) pyrimidine
(Compound described in DE4034762)

Test Example 1) Test for cucumber gray mold (CGM)
A cucumber (variety: Sagamihanjiro) 12 days after sowing was prepared. The cotyledon part was cut off leaving about 2 cm of the cucumber leaf shaft. Separately, a 32cm x 24cm x 4.5cm (vertical x horizontal x height) plastic case was laid with a paper towel sufficiently dampened with water, and a net with feet was placed on the paper towel. . On the net, the cut-out cotyledon portions were arranged so that the leaves were horizontal. In the middle of the cotyledons, 20 μl of a spore suspension (1 × 10 ⁶ cells / ml) of cucumber gray mold fungus (Botrytis cinerea) was dropped. Thereafter, a paper disk having a diameter of 8 mm was put on the cotyledons. An emulsion of the pyrimidine derivative of the present invention or a salt thereof was prepared according to Formulation Example 2 above, and further diluted with a 0.02% Tween20 demineralized water solution to prepare a diluted solution having a concentration of 500 ppm. 50 μl of this diluted solution was dropped from the top of the paper disk. After covering the plastic case and placing it at 20 ° C. for 96 hours, the lesion diameter was measured, and the control value of cucumber gray mold was determined by the following formula.

Control value (%) = [1− (Disease diameter of treated area / Disease diameter of untreated area)] × 100






















Table 4 Test results for Test Example 1)

Test Example 2) Test for kidney bean gray mold (KGM)
Green beans grown in a 6 cm diameter pot (variety: during Taishokin) were prepared for testing. Separately, an emulsion of the pyrimidine derivative of the present invention or a salt thereof was prepared according to Formulation Example 2 above, and further diluted with a 0.02% Tween20 demineralized water solution to prepare a diluted solution having a concentration of 500 ppm. A sufficient amount (approximately 0.025 ml / cm ² leaf surface area) of this diluted solution was sprayed on the leaf surface of the kidney beans using a spray gun. One day after air-drying, a spore suspension of Botrytis cinerea (5 × 10 ⁶ / ml 1/2 PS liquid medium containing 0.05% inosinic acid) is sprayed evenly on the leaf surface of kidney beans with a spray gun. (Surface area of about 0.01 ml / cm ² leaf). The green beans were then placed in an inoculation box at 23 ° C. and 100% humidity. Four days after the inoculation, the lesion area rate formed on the leaves was investigated using the following indices, and the control value of kidney bean gray mold was calculated using the following formula.

1: lesion area rate less than 6.3% severity 6.25
2: Rate of lesion area 6.3 to less than 12.5% Disease severity 12.5
3: Incidence rate 12.5 to less than 25% Disease severity 25.0
4: Disease area ratio 25 to less than 50% Disease severity 50.0
5: Incidence rate 50% or more Disease severity 100.0

Control value (%) = [1-(Severity of treated area / Severity of untreated area)] x 100

Table 5 Test results for Test Example 2)

Test Example 3) Test for cucumber downy mildew (CDM)
A 1.5-leaf cucumber (variety: Sagamihanjiro) grown in a 4 cm diameter pot was prepared for testing. Separately, an emulsion of the pyrimidine derivative of the present invention or a salt thereof was prepared according to Formulation Example 2 above, and further diluted with a 0.02% Tween20 demineralized water solution to prepare a diluted solution having a concentration of 500 ppm. A sufficient amount (approximately 0.025 ml / cm ² leaf surface area) of this diluted solution was sprayed on the leaf surface of the cucumber using a spray gun. One day after air drying, sprayed with a zoospore suspension of cucumber downy mildew (Pheudoperonospora cubensis) (approximately 0.001 ml / cm ² leaf surface area), inoculated with the fungus, and overhumidity at 23 ° C with 100% humidity After being left in the inoculation box for 24 hours, it was maintained in a 23 ° C. greenhouse for 4 days. Five days after the inoculation, the lesion area ratio formed on the leaves was determined in the same manner as in Test Example 2, and the control value of cucumber downy mildew was calculated according to the same formula as in Test Example 2.

Table 6 Test results for Test Example 3)

Test Example 4) Tomato plague test (TLB)
A three-leaf stage tomato (variety: large Fuju) grown in a 4 cm diameter pot was prepared for testing. Separately, an emulsion of the pyrimidine derivative of the present invention or a salt thereof was prepared according to Formulation Example 2 above, and further diluted with a 0.02% Tween20 demineralized water solution to prepare a diluted solution having a concentration of 500 ppm. A sufficient amount (approximately 0.025 ml / cm ² leaf surface area) of this diluted solution was sprayed on the leaf surface of the tomato using a spray gun. One day after air-drying, spray inoculation with a zoospore suspension of Phytophthora infestans (surface area of about 0.001 ml / cm ² leaves) and inoculation with fungus at 23 ° C and 100% humidity After being left in the inoculation box for 24 hours, it was maintained in a 23 ° C. greenhouse for 4 days. Five days after the inoculation, the lesion area ratio formed on the leaves was determined in the same manner as in Test Example 2, and the control value of the tomato blight was calculated according to the same formula as in Test Example 2.

Table 7 Test results for Test Example 4)

Test Example 5) Wheat red rust test (WBR)
Two-leaf wheat (variety: Norin 61) grown in a 4 cm diameter pot was prepared for testing. Separately, an emulsion of the pyrimidine derivative of the present invention or a salt thereof was prepared according to Formulation Example 2 above, and further diluted with a 0.02% Tween20 demineralized water solution to prepare a diluted solution having a concentration of 500 ppm. A sufficient amount (approximately 0.025 ml / cm ² leaf surface area) of this diluted solution was sprayed on the wheat using a spray gun. One day after air-drying, spray a summer spore suspension of wheat rust (Puccinia recondeta) (approximately 0.01 ml / cm ² leaf surface area) to inoculate the fungus, and inoculate at 23 ° C with 100% humidity. After being left in the box for 24 hours, it was maintained in a 23 ° C. greenhouse for 6 days. Seven days after the inoculation, the lesion area ratio formed on the leaves was determined in the same manner as in Test Example 2, and the control value of wheat rust was calculated according to the same formula as in Test Example 2.

Table 8 Test results for Test Example 5)

Test Example 6) Test for barley powdery mildew (BPM)
Two-leaf barley (variety: Minorimugi) grown in a pot of 4 cm diameter was prepared for testing. Separately, an emulsion of the pyrimidine derivative of the present invention or a salt thereof was prepared according to Formulation Example 2 above, and further diluted with a 0.02% Tween20 demineralized water solution to prepare a diluted solution having a concentration of 500 ppm. A sufficient amount (about 0.025 ml / cm ² leaf surface area) of this diluted solution was sprayed on the barley using a spray gun. One day after air-drying, conidia were inoculated by sprinkling with conidia of barley powdery mildew (Erysiphe graminis) and maintained in a 23 ° C. greenhouse for 6 days. Seven days after the inoculation, the lesion area ratio formed on the leaves was determined in the same manner as in Test Example 2, and the control value of barley powdery mildew was calculated according to the same formula as in Test Example 2.

Table 9 Test results for Test Example 6)

防除価（％） = [1 - （処理区発病度 / 無処理区発病度）] x 100 Test Example 7) Test for kidney bean leaf rot (KRR)
Kidney bean (variety: at Taishokin) primary leaves grown in a 6 cm diameter pot was prepared for testing. Separately, an emulsion of the pyrimidine derivative of the present invention or a salt thereof was prepared according to Formulation Example 2 above, and further diluted with a 0.02% Tween20 demineralized water solution to prepare a diluted solution having a concentration of 500 ppm. A sufficient amount (approximately 0.025 ml / cm ² leaf surface area) of this diluted solution was sprayed on the leaf surface of the kidney beans using a spray gun. One day after air-drying, a leaf disc 3 cm in diameter is cut from the primary leaves and a paper towel moistened with water is placed on the bottom of a 32 cm x 24 cm x 4.5 cm (vertical x horizontal x height) plastic case. The leaf discs were arranged on this paper towel. A flora agar piece of kidney bean leaf rot fungus (Rhizoctonia solani) was placed in the center of the leaf disk, and the plastic case was covered and placed at 23 ° C. for 72 to 96 hours. Then, the lesion area rate of each leaf disk was investigated using the following indicators, and the control value of kidney bean leaf rot fungus was determined from the following formula.

Control value (%) = [1-(Severity of treated area / Severity of untreated area)] x 100

Table 10 Test results for Test Example 7)

Test Example 8) Effect at Low Concentration on Various Pathogenic Bacteria Similar to Test Examples 1) and 3) to 5) except that the concentration of the pyrimidine derivative of the present invention or its salt emulsion was changed to 100 ppm or 20 ppm. These tests were repeated, and the effects of the pyrimidine derivative of the present invention or a salt thereof on various pathogenic bacteria under a low concentration were measured. Table 11 shows the control value (%) against various pathogens.








Table 11

Test Example 9) Effect on weeds by foliage treatment
A 15 × 10 cm aluminum pot was filled with field soil, and seeds of soybean seeds / cm ² and corn seeds 1 / cm ^{2 were} sown as useful crops. This soil, further broadleaf weeds seeds as slender amaranth and 10 grains / cm ^2, after seeding 10 seeds / cm ² and common lambsquarters were subjected to 0.5cm cover soil. When aoubi is in the second to third leaf stage, the dose of 3 kg / ha (30 g ai / a) of the emulsion of the pyrimidine derivative of the present invention prepared according to Formulation Example 2 or a salt thereof is uniformly soybean. , Sprayed on the stalks and leaves of corn and aoubi. After 14 days of the spraying treatment, the growth state of Aoubi was observed and the effect was judged. The degree of growth was divided into 10 levels of 1 to 10 (1 indicates no treatment equivalent, 10 indicates complete death). The effect was determined by repeating the same method as described above except that Shiroza was used as the broad-leaved weed seed.
Table 12

Test Example 10) Effect on Kanzawa spider mite larva Green beans were cut into 2.5 cm × 5.0 cm with scissors to prepare leaf discs. Separately, a glass disk having a diameter of 12.0 cm was placed on the bottom of the polystyrene cup, and a filter paper moistened with water was placed on the glass disk. The two leaf discs were left on the filter paper. In addition, ten female Kanzawa spider mites were placed per leaf disk. After standing for 24 hours, an aqueous dilution (concentration of 500 ppm) of an emulsion of the pyrimidine derivative of the present invention or a salt thereof prepared according to Formulation Example 2 was sprayed using a chromatographic sprayer in an amount of 5 ml for each styrene cup. After further air drying for 24 hours, the leaf disc was placed in a thermostat at 26 ° C. to remove the adult female so that only the eggs born by the adult female remained on the leaf disc. Seven days after spraying, the mortality rate of born larvae was calculated according to the following formula.

Larval death rate (%) = [Number of dead insects / (Number of dead insects + Number of surviving insects)] × 100




Table 13

Claims (3)

Formula [I]

[Wherein R ¹ represents an alkyl group or an alkoxy group;
R ² represents an arylalkyl group or a heteroarylalkyl group;
R ³ represents a hydrogen atom, a halogen atom or an alkyl group;
n represents 0, 1 or 2,
Het is the formula [II]

(Wherein R ⁴ represents a hydrogen atom, a hydroxyl group, a halogen atom, an alkyl group or an alkoxy group, which may be the same or different, and represents an aryl group, heteroaryl group, cyano group, nitro group, amino group, alkylamino group, dialkyl. Represents an amino group, an alkylthio group, an alkylsulfinyl group or an alkylsulfonyl group, and m represents an integer of 1 to 4.
Or a salt thereof. (1) Formula [III]

[Wherein, Het, R ¹ and R ³ represent the same meaning as in claim 1 and X represents a halogen atom]
A compound represented by
Formula [IV]

[Wherein R ² represents the same meaning as defined in claim 1], or a compound represented by the formula [V]

[Wherein Het, R ¹ , R ³ represent the same meaning as in claim 1],
Formula [VI]

[Wherein R ² represents the same meaning as in claim 1, X represents a halogen atom] and a compound represented by the formula [VII]

[Wherein Het, R ¹ , R ² , R ³ represent the same meaning as in claim 1], and a step of obtaining a compound represented by:
(2) oxidizing the obtained compound represented by the formula [VII] to obtain the pyrimidine derivative according to claim 1;
The manufacturing method of the pyrimidine derivative or its salt of Claim 1 containing this. A pest control agent comprising one or more of the pyrimidine derivatives or salts thereof according to claim 1 as an active ingredient.