JP2003064059A - Pyrimidine compound, method for producing the same and herbicide - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a new pyrimidine compound and its salt capable of providing an active ingredient of a safely usable herbicide having sure effects, a method for producing the same and the herbicide comprising the pyrimidine compound or its salt as the active ingredient. SOLUTION: This pyrimidine compound is represented by the general formula (1) (wherein, R1 denotes a 1-6C alkyl group, a 3-6C cycloalkyl group, a 1-6C haloalkyl group or the like; R2 and R3 denote each independently a 1-6C alkyl group, a 3-6C cycloalkyl group or a 1-6C haloalkyl group; R4 denotes hydrogen atom, a 1-4C alkyl group or the like; X denotes a halogen atom, a 1-4C alkyl group, a 1-3C haloalkyl group or the like; and n denotes 0 or an integer of 1-5). The method for producing the same is provided and the herbicide comprises the compound or its salt.

Description

Detailed Description of the Invention

TECHNICAL FIELD The present invention relates to a novel pyrimidine compound, a method for producing the same, and a herbicide containing the pyrimidine compound as an active ingredient.

[0001]

2. Description of the Related Art In connection with the present invention, for example, Japanese Unexamined Patent Publication No. 8-
No. 291168 discloses the following formula (B)

[0002]

[Chemical 10]

(In the formula, X'represents a halogen atom such as a chlorine atom, _R'represents a hydrogen atom, a C _1-8 alkyl group, etc., and Q represents a saturated C _{1-6 optionally} branched chain. Alternatively, a pyrimidine compound represented by an unsaturated carbon chain, Ar represents a halogen atom, a phenyl group which may be substituted with a substituent such as a C _1-6 alkyl group, a pyridyl group, or the like) has a herbicidal activity. It is stated that it has.

However, this document does not describe a compound having a substituent at the 2- and 4-positions of pyrimidine and an N-benzylcarbamoyl group at the 5-position as in the present invention.

[0005]

DISCLOSURE OF THE INVENTION The present invention comprises a novel pyrimidine compound and a salt thereof which can be safely used as an active ingredient of a herbicide which can be safely used, a method for producing the same, and a pyrimidine compound or a salt thereof as an active ingredient. It is an object to provide a herbicide that does

[0006]

[Means for Solving the Problems] In order to solve the above problems,
The present invention is firstly represented by the general formula (1)

[0007]

[Chemical 11]

[0008] (wherein, R1 is a halogen atom, C _1-6 alkyl groups, C _3-6 cycloalkyl groups, C _1-6 haloalkyl group, C _1-6 alkoxy groups, C _3-6 cycloalkoxy groups, C
_1-6 haloalkoxy group, C _1-6 alkylamino group, C _1-6
Represents a haloalkylamino group, a diC _1-6 alkylamino group, a hydroxyl group or an amino group, and represents R 2, R 3
Each independently represents a C _1-6 alkyl group, a C _3-6 cycloalkyl group or a C _1-6 haloalkyl group, R 4
_{Represents a} hydrogen atom, a C _1-4 alkyl group, a C _1-4 alkoxy group or a hydroxyl group, and X represents a halogen atom, C
_1-4 alkyl group, C _3-6 cycloalkyl group, C _1-3 haloalkyl group, C _1-4 alkoxy group, C _1-3 haloalkoxy group, cyano group, nitro group, phenyl optionally substituted with A Oxy group, C _1-4 alkoxycarbonyl group, mono C _1-4
Represents an alkylcarbamoyl group or a di-C _1-4 alkylcarbamoyl group, wherein A represents a halogen atom, a C _1-4 alkyl group, a C _1-4 alkoxy group, a C _1-4 haloalkyl group, a nitro group or a cyano group And n represents 0 or an integer of 1 to 5. ) The pyrimidine compound represented by these or its salt is provided. The present invention secondly provides an optically active form of the compound represented by the general formula (1). The present invention is thirdly
General formula (2),

[0009]

[Chemical 12]

(In the formula, R2 represents a C _1-6 alkyl group, a C _3-6 cycloalkyl group or a C _1-6 haloalkyl group, and L ₁ and L ₂ each independently represent a leaving group. .) And a compound represented by the general formula (3):

[0011]

[Chemical 13]

(In the formula, R4 represents a hydrogen atom, a C _1-4 alkyl group, a C _1-4 alkoxy group or a hydroxyl group, R 3 represents a C _1-6 alkyl group, a C _3-6 cycloalkyl group,
Alternatively, it represents a C _1-6 haloalkyl group, X is a halogen atom, a C _1-4 alkyl group, a C _3-6 cycloalkyl group, a C _1-3
Haloalkyl group, C _1-4 alkoxy group, C _1-3 haloalkoxy group, cyano group, nitro group, phenyloxy group which may be substituted with A, C _1-4 alkoxycarbonyl group, mono C _1-4 alkylcarbamoyl Or a diC _1-4 alkylcarbamoyl group, A is a halogen atom, a C _1-4 alkyl group, a C _1-4 alkoxy group, a C _1-4 haloalkyl group,
Represents a nitro group or a cyano group, n is 0 or 1 to
Represents an integer of 5. ) Is reacted with a compound represented by the general formula (4)

[0013]

[Chemical 14]

(Wherein R2, R3, R4, L ₁ , X and n have the same meanings as described above), and a step of obtaining the compound represented by the general formula (4). Compounds and general formula (5)

[0015]

[Chemical 15] R5H (5)

(In the formula, R 5 is a C _1-6 alkoxy group, C _3-6
Cycloalkoxy group, C _1-6 haloalkoxy group, C _1-6 alkylamino group, C _1-6 haloalkylamino group, di-C _1-6
It represents an alkylamino group, a hydroxyl group, or an amino group. ) Having a step of reacting with a compound represented by the formula (1-1)

[0017]

[Chemical 16]

There is provided a process for producing a pyrimidine compound represented by the formula (wherein R2, R3, R4, R5, X and n have the same meanings as described above). Fourthly, the present invention relates to general formula (6)

[0019]

[Chemical 17]

(In the formula, R2 represents a C _1-6 alkyl group, a C _3-6 cycloalkyl group or a C _1-6 haloalkyl group, and R 6 represents a C _1-6 alkyl group, a C _3-6 cycloalkyl group. Base,
C _1-6 haloalkyl group, C _{1 -6} alkoxy, C _3-6 cycloalkoxy group, C _1-6 haloalkoxy group, or a di-C _1-6 alkylamino group. ) And a compound represented by the general formula (7)

[0021]

[Chemical 18]

(In the formula, R3 represents a C _1-6 alkyl group, a C _3-6 cycloalkyl group or a C _1-6 haloalkyl group, and R 7 represents a hydrogen atom, a C _1-4 alkyl group or a C _1-6 alkyl group. _1-4
Represents an alkoxy group, X represents a halogen atom, a C _1-4 alkyl group, a C _3-6 cycloalkyl group, a C _1-3 haloalkyl group,
A C _1-4 alkoxy group, a C _1-3 haloalkoxy group, a cyano group, a nitro group, a phenyloxy group which may be substituted with A, a C _1-4 alkoxycarbonyl group, a mono C _1-4 alkylcarbamoyl group, or Represents a di C _1-4 alkylcarbamoyl group, A is a halogen atom, a C _1-4 alkyl group, C
_1-4 alkoxy group, C _1-4 haloalkyl group, nitro group or cyano group, and n represents 0 or an integer of 1 to 5. General formula (1-2) which has the process of reacting with the compound represented by these in the coexistence of a dehydration condensation agent.

[0023]

[Chemical 19]

A method for producing a pyrimidine compound represented by the formula (wherein R2, R3, R6, R7, X and n have the same meanings as described above) is provided. Fifth, the present invention relates to a pyrimidine compound represented by the general formula (1) or a salt thereof.
Provided is a herbicide, which comprises one or two or more species as an active ingredient.

[0025]

BEST MODE FOR CARRYING OUT THE INVENTION Hereinafter, the compound of the present invention and its compound
The salt, its production method and herbicide will be explained in detail.
It The compound of the present invention is represented by the general formula (1).
In the above-mentioned general formula (1) which is a compound and a salt thereof,
R1 is a halogen atom such as fluorine, chlorine, bromine or iodine;
Methyl group, ethyl group, n-propyl group, isopropyl
Group, n-butyl group, sec-butyl group, t-butyl group,
C such as n-pentyl group and n-hexyl group_1-6Alkyl
Group; cyclopropyl group, cyclopentyl group, cyclohexyl
C such as sil group_3-6Cycloalkyl group; trifluoromethyl
Group, pentafluoroethyl group, chlorodifluoromethyl group
C such as ru radical_{1- 6}Haloalkyl group; methoxy group, ethoxy
Group, n-propoxy group, isopropoxy group, n-butoxy group
Si group, t-butoxy group, n-pentyloxy group, n-hexyl group
C such as xyloxy group_1-6Alkoxy group; cyclopropene
Luoxy group, cyclopentyloxy group, cyclohexyl
C such as oxy group_3-6Cycloalkoxy group; 2,2,2-
Trifluoroethoxy group, 2,2,3,3-tetraflu
C such as oropropoxy group _1-6Haloalkoxy group; methyl
Amino group, ethylamino group, n-propylamino group, a
C such as sopropylamino group and n-butylamino group_1-6A
Rukylamino group; 2,2,2-trifluoroethylami
Group, 1,1,1-trifluoro-2-propylamino
C etc._1-6Haloalkylamino group; dimethylamino
Group, di-n-propylamino group, diisopropylamino
Group C_1-6Alkylamino group; hydroxyl group;
Or R2 and R3 each independently represent an amino group.
Methyl group, ethyl group, n-propyl group, isopropyl
Group, n-butyl group, sec-butyl group, t-butyl group,
C such as n-pentyl group and n-hexyl group_1-6Alkyl
Group; cyclopropyl group, cyclopentyl group, cyclohexyl
C such as sil group_3-6Cycloalkyl group; or triflu
Oromethyl group, pentafluoroethyl group, chlorodiflu
C such as oromethyl group_1-6Represents a haloalkyl group, R4 is
Hydrogen atom; methyl group, ethyl group, n-propyl group, iso
Propyl group, n-butyl group, sec-butyl group, t-butyl
C such as chill group_1-4Alkyl group; methoxy group, ethoxy
Group, n-propoxy group, isopropoxy group, n-butoxy group
C, such as Si group and t-butoxy group_1-4Alkoxy group;
Represents a hydroxyl group, X represents fluorine, chlorine, bromine,
Halogen atom such as iodine; methyl group, ethyl group, n-type
C such as ropyl group and isopropyl group_1-4Alkyl group;
C such as propyl_3-6Cycloalkyl group; trifluoro
C such as methyl group_1-3Haloalkyl group; methoxy group, eth
C such as xy group, n-propoxy group and isopropoxy group
_1-4Alkoxy group; C such as trifluoromethoxy group_1-3Ha
Alkoxy group; cyano group; nitro group; substituted with A
Good phenyloxy group; methoxycarbonyl group, eth
C such as oxycarbonyl group and n-propoxycarbonyl group
_1-4Alkoxycarbonyl group; methylcarbamoyl group,
Ethylcarbamoyl group, n-propylcarbamoyl group, etc.
Mono C_1-4An alkylcarbamoyl group; or dimethy
Di-C such as lucarbamoyl group and diethylcarbamoyl group
_1-4Represents an alkylcarbamoyl group, A is fluorine, salt
Halogen atom such as elemental, bromine, iodine; methyl group, ethyl
Group C _1-4Alkyl group; methoxy group, ethoxy group, n-
C such as propoxy group and isopropoxy group_1-4Alkoxy
Group; C such as trifluoromethyl group_1-4Haloalkyl group;
Nitro group; or cyano group, these substituents
Are the same or different and have a plurality of phenyloxy groups.
N may represent 0 or an integer of 1-5.
You When n represents an integer of 2 or more, X may be the same or different.
The salt of the compound of the present invention which may be present is acceptable as a herbicide.
Salts of sodium, potassium, etc.
Lucari metal salt; alkali such as magnesium and calcium
Examples include earth metal salts; ammonium salts and the like. Invented
The compound may have diastereomers and geometric isomers.
It All of their mixtures and isolated isomers
Included in the invention. Further, the compound of the present invention has an asymmetric carbon atom.
As such, it has an optically active substance. Light of the compound of the present invention
Diastereomeric mixtures are prepared by conventional optical resolution methods such as optical
Optical resolution can be achieved by a method that uses a column for resolution.
Wear. The separated optically active substance is a mixture of optical isomers and other
May show excellent herbicidal activity against the optical isomers of
It

The compound of the present invention can be produced by the following method. (Production method 1)

[0027]

[Chemical 20]

(Wherein R2, R3, R4, R5, X,
n, L ₁ and L ₂ have the same meanings as described above. The compound represented by the general formula (1-1) includes a compound represented by the general formula (2) and a compound represented by the general formula (3).
1 to 48 at a reaction temperature of −50 ° C. to 200 ° C., preferably −20 ° C. to 50 ° C. in a solvent in the presence of a base.
After reacting for a time to obtain the compound represented by the general formula (4), the obtained compound represented by the general formula (4) and the compound represented by the general formula (5) are treated in an inert solvent. Alternatively, it can be obtained by reacting without a solvent in the presence of a base at a reaction temperature of -50 to 200 ° C, preferably a reaction temperature of 0 ° C to 100 ° C.

Examples of the solvent which can be used for producing the compound represented by the general formula (4) include amines such as triethylamine and tributylamine; aromatic hydrocarbons such as benzene and toluene; tetrahydrofuran (THF) and dioxane. Ethers such as; amides such as N, N-dimethylformamide (DMF) and N, N-dimethylacetamide; halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride; acetonitrile; dimethyl sulfoxide, etc. can give. Among these, the use of ethers is preferable from the viewpoint of obtaining the desired product in good yield.

As the base, triethylamine,
An organic base such as diisopropylethylamine, tributylamine or pyridine; an inorganic base such as sodium carbonate or potassium carbonate can be used. Among these, the use of an organic base is preferable from the viewpoint of obtaining the desired product in good yield.

Examples of the solvent that can be used in the reaction for producing the compound represented by the general formula (1-1) from the compound represented by the general formula (4) include, for example, aromatic carbonization such as benzene and toluene. Hydrogens; ethers such as THF and dioxane; amides such as DMF, N, N-dimethylacetamide; halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride; acetonitrile; dimethyl sulfoxide, etc. . Among these, use of ethers is preferable from the viewpoint of obtaining the desired product in good yield.

As the base, triethylamine,
Amines such as dimethylamine; inorganic bases such as sodium hydride and potassium carbonate; metal alkoxides such as sodium methoxide, sodium ethoxide, potassium t-butoxide; and the like can be used. Among these, the use of metal alkoxides is preferable from the viewpoint of obtaining the desired product in good yield.

(Production Method 2) The compound represented by the general formula (1-2) can be produced by the following method.

[0034]

[Chemical 21]

(In the formula, R2, R3, R6, R7, X and n have the same meanings as described above.) That is, the compound represented by the general formula (1-2) is represented by the general formula (6). A compound represented by the general formula (7) and a compound represented by the general formula (7) are reacted in a solvent in the presence of a condensing agent and optionally a catalyst at a reaction temperature of −50 ° C. to 200 ° C., preferably −2.
It can be obtained by reacting at a reaction temperature of 0 ° C to 50 ° C.

Examples of the solvent which can be used in this reaction include halogenated hydrocarbons such as methylene chloride and chloroform; esters such as ethyl acetate; aromatic hydrocarbons such as benzene and toluene; diethyl ether and TH.
Ethers such as F and dioxane; acetonitrile; DM
F: Dimethyl sulfoxide and the like can be mentioned. Among these, the use of halogenated hydrocarbons is preferable from the viewpoint of obtaining the desired product in good yield.

Examples of condensing agents that can be used include N, N'-dicyclohexylcarbodiimide, N-
(3-Dimethylamino) propyl-N'-ethylcarbodiimide (hydrochloride, methiodide) and the like can be mentioned. Further, as the catalyst, for example, N, N-dimethylaminopyridine or the like can be used. By using a catalyst, the reaction may be allowed to proceed smoothly.

In any reaction, the desired product can be efficiently isolated by performing usual post-treatment and purification after completion of the reaction. The structure of the compound of the present invention can be determined from IR, NMR, MASS spectra and the like.

Table 1 shows examples of the compounds included in the present invention. The abbreviations in the table have the following meanings. Me: methyl group, Et: ethyl group, Pr: propyl group,
Bu: butyl group, n: normal, i: iso, t: tertiary, c: cyclo Moreover, the abbreviations in the column of skeleton in Table 1 show the following skeletons.

[0040]

[Chemical formula 22]

[0041]

[Table 1]

[0042]

[Table 2]

[0043]

[Table 3]

[0044]

[Table 4]

[0045]

[Table 5]

[0046]

[Table 6]

[0047]

[Table 7]

[0048]

[Table 8]

[0049]

[Table 9]

[0050]

[Table 10]

[0051]

[Table 11]

[0052]

[Table 12]

[0053]

[Table 13]

[0054]

[Table 14]

[0055]

[Table 15]

[0056]

[Table 16]

[0057]

[Table 17]

[0058]

[Table 18]

[0059]

[Table 19]

[0060]

[Table 20]

[0061]

[Table 21]

[0062]

[Table 22]

[0063]

[Table 23]

[0064]

[Table 24]

[0065]

[Table 25]

[0066]

[Table 26]

[0067]

[Table 27]

[0068]

[Table 28]

[0069]

[Table 29]

[0070]

[Table 30]

[0071]

[Table 31]

[0072]

[Table 32]

The compound of the present invention [a compound represented by the general formula (1) or a salt thereof] exhibits a high herbicidal activity under any of the methods of soil treatment and foliage treatment under field cultivation conditions. It is effective for various field weeds such as Inubiyu and Azusa. The compounds of the present invention include compounds showing selectivity for crops such as corn, wheat, soybean, and cotton. The compound of the present invention includes a compound having a plant growth regulating action such as a growth inhibiting action on useful plants such as crops, ornamental plants and fruit trees. The compound of the present invention includes a compound which has an excellent herbicidal activity against rice paddy weeds such as Nobie, Tamagawai, Omodaka and Firefly, and shows selectivity for rice. The compound of the present invention can also be applied to control weeds in orchards, lawns, railroad ends, vacant lots and the like. The compounds of the present invention also include those having plant growth regulating action, bactericidal activity, and insecticidal / miticidal activity. Further, the intermediate compounds of the compound of the present invention include those having herbicidal activity, plant growth regulating activity, bactericidal activity, and insecticidal / miticidal activity.

The herbicide of the present invention comprises one or more compounds of the present invention as an active ingredient. When the compound of the present invention is actually applied, it can be used in a pure form without adding other components, and can be a form of a general agricultural chemical for the purpose of being used as an agricultural chemical, that is, a wettable powder, granules, powder, It can also be used in the form of emulsion, water solvent, suspension, flowable, and the like.

When a solidifying agent is intended, as additives and carriers, for example, vegetable powder such as soybean flour and wheat flour,
Mineral fine powders such as diatomaceous earth, apatite, gypsum, talc, bentonite, pyrophyllite and clay, and organic and inorganic compounds such as sodium benzoate, urea and mirabilite are used.
When intended for liquid dosage forms, for example, kerosene, petroleum fractions such as xylene and solvent naphtha, cyclohexane, cyclohexanone, dimethylformamide, dimethyl sulfoxide, alcohol, acetone, trichloroethylene, methyl isobutyl ketone, mineral oil, vegetable oil. , Water or the like can be used as a solvent.

Further, in order to obtain a uniform and stable form in these preparations, a surfactant can be added if necessary. The surfactant is not particularly limited, and examples thereof include polyoxyethylene-added alkyl phenyl ether, polyoxyethylene-added alkyl ether, polyoxyethylene-added higher fatty acid ester, and polyoxyethylene-added sorbitan. Nonionic surfactants such as higher fatty acid esters and polyoxyethylene-added tristyryl phenyl ethers,
Sulfonate ester of alkylphenyl ether with polyoxyethylene added, alkylnaphthalene sulfonate, polycarboxylate, lignin sulfonate, formaldehyde condensate of alkylnaphthalene sulfonate,
An isobutylene-maleic anhydride copolymer or the like can be used.

The concentration of the active ingredient in the herbicide of the present invention varies depending on the form of the above-mentioned preparation. For example, in the wettable powder, the concentration is 5 to 90% by weight (hereinafter, simply referred to as "% ], Preferably 10-85.
% In emulsions, preferably 3 to 70%, preferably 5
-60%, and in granules, 0.01-50%,
The concentration is preferably 0.05 to 40%.

The wettable powder and emulsion thus obtained are diluted with water to a predetermined concentration to give a suspension or emulsion.
The granules are sprayed or mixed on the soil as it is before or after germination of the weeds. When actually applying the herbicide of the present invention, the active ingredient is 0.1 per hectare.
An appropriate amount of at least g is applied.

The herbicide of the present invention can also be used as a mixture with known fungicides, insecticides, acaricides, herbicides, plant growth regulators, fertilizers and the like. In particular, it is possible to reduce the dose used by mixing with a herbicide. Further, not only labor saving but also higher effect can be expected due to the synergistic action of the mixed drug. In that case, a combination with a plurality of known herbicides is also possible.

Suitable agents to be mixed with the herbicide of the present invention include anilide herbicides such as difluphenican and propanil; chloroacetanilide herbicides such as alachlor and pretilachlor; 2,4-D, 2,4-D.
Aryloxyalkanoic acid type herbicides such as B; Aryloxyphenoxyalkanoic acid type herbicides such as diclofop-methyl and phenoxaprop-ethyl; Arylcarboxylic acid type herbicides such as dicamba and pyrithiobac; Imidazoline type such as imazaquin and imazethapyr Herbicides: Urea herbicides such as diuron and isoproturon; Carbamate herbicides such as chlorpropham and fenmedifam; Thiocabamate herbicides such as thiobencarb and EPTC; Dinitroaniline herbicides such as trifluralin and pendimethalin; Aci Diphenyl ether herbicides such as fluorfen and fomesafen; Sulfonylurea herbicides such as bensulfuron-methyl and nicosulfuron; Triazinone herbicides such as metribuzin and metamitron;
Triazine herbicides such as atrazine and cyanazine; triazopyrimidine herbicides such as flumetulum; nitrile herbicides such as bromoxynil and diclobenil; phosphate herbicides such as glyphosate and glyphosinate; paraquat,
Quaternary ammonium salt type herbicides such as diphenzocoat; cyclic imide type herbicides such as flumicrolac-pentyl and furthiaset-methyl; and benzoylaminopropionic acid type herbicides such as benzoylpropethyl and furanpropethyl.

In addition, isoxaben, etofumesate, oxadiazone, piperofos, dimuron, bentazone, benflusate, daifenzocoat, naproanilide, triazophenamide, quinclorac, clomazone, sulcotrione, cinmethyline, dithiopyr, pyrazolate, pyridate, Full poxam,
Further, cyclohexanedione-based herbicides such as setoxydim and tralkoxydim are listed. Further, additives such as vegetable oils and oil concentrates can be added to the composition obtained by combining these.

[0082]

EXAMPLES Next, the compounds of the present invention will be explained in more detail with reference to Examples and Reference Examples, but the present invention is not limited to the following Examples. Reference Example 1 Synthesis of 2-chloro-N- [1- (4-trifluoromethylphenyl) -ethyl] -4-trifluoromethyl-5-pyrimidinecarboxamide

[0083]

[Chemical formula 23]

1- (4-trifluoromethylphenyl)
4.56 g of ethylamine and 2.
To a solution of 43 g of dioxane in 50 ml, 2-chloro-4-
Trifluoromethyl-5-pyrimidine carbonyl chloride (4.71 g) was added, and the mixture was stirred at room temperature for 3 hours. The solvent was distilled off from the reaction solution, water was added to the residue, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and filtered. The residue obtained by depressurizing the filtrate was subjected to silica gel column chromatography (developing solvent: n-hexane:
The product was purified with ethyl acetate = 5: 1) to obtain 1.35 g of the desired product. Yield 18%, melting point 156-158 ° C

Example 1 Synthesis of 2-methoxy-N- [1- (4-trifluoromethylphenyl) -ethyl] -4-trifluoromethyl-5-pyrimidinecarboxamide (Compound No. 9)

[0086]

[Chemical formula 24]

0.75 g of 2-chloro-N- [1- (4-trifluoromethylphenyl) -ethyl] -4-trifluoromethyl-5-pyrimidinecarboxamide was dissolved in 30 ml of methanol and added with 28% sodium methoxy. 0.44 g of methanol solution of sodium hydroxide was added, and the mixture was stirred at room temperature for 2 hours. The solvent was distilled off from the reaction solution, water was added, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated to give crude crystals. The obtained crystals were washed with n-hexane to obtain 0.7
4 g was obtained. Yield 99% Melting point: 125-127 ° C

Example 2 2-Methoxy-N-methyl-N- [1- (4-trifluoromethylphenyl) -ethyl] -4-trifluoromethyl-5-pyrimidinecarboxamide (Compound No.
Synthesis of 10)

[0089]

[Chemical 25]

2-Methoxy-N- [1- (4-trifluoromethylphenyl) -ethyl] -4-trifluoromethyl-5-pyrimidinecarboxamide 0.54 g of D
0.05 g of sodium hydride was added to 10 ml of MF solution, and the mixture was stirred at room temperature for 1 hour. 0.19 g of methyl iodide there
Was added, and the mixture was further stirred overnight. Water was added to the reaction solution and extracted with ethyl acetate, the organic layer was dried over anhydrous magnesium sulfate and filtered. The residue obtained by concentrating the filtrate under reduced pressure was subjected to silica gel column chromatography (developing solvent: n-
Purified with hexane: ethyl acetate = 5: 1) to obtain the desired product.
27 g was obtained. 48% yield amorphous

Reference Example 2 2-chloro-N-hydroxy-N- [1- (4-chlorophenyl) -ethyl] -4-trifluoromethyl-5-
Synthesis of pyrimidine carboxamide

[0092]

[Chemical formula 26]

To a solution of 3.7 g of N-hydroxy-N- [1- (4-chlorophenyl) -ethyl] -amine and 2.18 g of triethylamine in 30 ml of dioxane was added 2-
Chloro-4-trifluoromethyl-5-pyrimidine carbonyl chloride (4.41 g) was added, and the mixture was stirred at room temperature for 3 hours. After distilling off the solvent from the reaction solution, water was added and the mixture was extracted with ethyl acetate, and the organic layer was dried over anhydrous magnesium sulfate,
Filtered. The residue obtained by concentrating the filtrate under reduced pressure was purified by silica gel column chromatography (developing solvent: n-hexane: ethyl acetate = 5: 1) to obtain 1.9 g of the desired product. 28% yield amorphous

Example 3 Synthesis of 2-methoxy-N- [1- (4-chlorophenyl) -ethyl] -4-trifluoromethyl-5-pyrimidinecarboxamide (Compound No. 11)

[0095]

[Chemical 27]

0.4 g of 2-chloro-N- [1- (4-chlorophenyl) -ethyl] -4-trifluoromethyl-5-pyrimidinecarboxamide was added to 20 ml of methanol.
Was dissolved in, and 0.24 g of sodium methoxide was added thereto, followed by stirring at room temperature for 2 hours. After the solvent was distilled off from the reaction solution, water was added and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure and the selected residue was purified by silica gel column chromatography (developing solvent: benzene: ethyl acetate = 3: 1) to obtain 0.22 g of the desired product. Yield 56% Amorphous

Example 4 2-Ethyl-N- [1- (2,4-dichlorophenyl)
-Ethyl] -4-trifluoromethyl-5-pyrimidinecarboxamide (Compound No. 3)

[0098]

[Chemical 28]

2-Ethyl-4-trifluoromethyl-5
-0.15 g of pyrimidinecarboxylic acid and 0.09 g of 1- (2,4-dichlorophenyl) -ethylamine were dissolved in 5 ml of methylene chloride, and 0.18 g of N- (3-dimethylamino) propyl-N'-ethylcarbodiimide was dissolved therein.
And 4-dimethylaminopyridine (0.06 g) were added, and the mixture was stirred at room temperature for 5 hours. Add chloroform to the reaction mixture,
The organic layer was separated. The organic layer was washed successively with 2N hydrochloric acid, water, saturated aqueous sodium hydrogen carbonate solution, and saturated brine, dried over anhydrous magnesium sulfate, and filtered. The residue obtained by concentrating the filtrate under reduced pressure was purified by silica gel column chromatography (developing solvent: n-hexane: ethyl acetate = 3: 1) to obtain 0.07 g of the desired product. Yield 42% Melting point 140-142 ° C

Representative examples of the compounds of the present invention obtained as described above including the above Examples are shown in Table 2. The abbreviations in the table have the same meanings as in Table 1. In Table 2, compound No. 2, 10, 11, 12, 13, 17, 37, 3
The ¹ H-NMR data of 8, 62 and 63 are shown in Table 3.

[0101]

[Table 33]

[0102]

[Table 34]

[0103]

[Table 35]

Next, some formulation examples relating to the herbicide of the present invention will be shown, but the active ingredient compounds, additives and addition ratios are not limited to this example, and can be varied within a wide range. The parts in the formulation examples represent parts by weight.

Example 5 Wettable Powder Compound of the present invention 20 parts White carbon 20 parts Diatomaceous earth 52 parts Sodium alkylsulfate 8 parts The above ingredients are uniformly mixed and finely ground to give a wettable powder containing 20% of the active ingredient. obtain.

[0106] (Example 6) Emulsion     20 parts of the compound of the present invention     Xylene 55 parts     Dimethylformamide 15 parts     Polyoxyethylene phenyl ether 10 parts The above are mixed and dissolved to obtain an emulsion containing 20% of the active ingredient.

(Example 7) Granules Compound of the present invention 5 parts Talc 40 parts Clay 38 parts Bentonite 10 parts Sodium alkyl sulfate 7 parts The above components are uniformly mixed and finely pulverized to give a diameter of 0.5 to 1.
Granulate into 0 mm granules to obtain granules containing 5% of the active ingredient.

[0108]

Next, test examples relating to the effects of the herbicide of the present invention will be shown. The herbicidal effect was investigated according to the following criteria and expressed as a herbicidal index.

Survey Criteria Slaughter rate Slaughter index 0% 0 20-29% 2 40-49% 4 60-69% 680 80-89% 8 100% 10 Also, 1, 3, 5, 7, 9 Numerical values indicate intermediate values of 0 and 2, 2 and 4, 4 and 6, 6 and 8, and 8 and 10, respectively.

[0110]

[Equation 1]              (Aerial vegetation weight of untreated area-Aerial vegetation weight of treated area)   Weeding rate (%) = × 100                           Above-ground fresh grass weight of untreated area

(Test Example 1) Field Stalk and Leaf Spraying A plastic pot having a surface area of 200 cm ² was filled with field soil, and various seeds of Inubiyu and Akaza were sown on the surface layer, lightly covered with soil, and then grown in a greenhouse. At the time when each weed grew to a plant height of 5 to 10 cm, the water dilution of the emulsion of each test compound shown in Example 6 was added to 100 g of the active ingredient per 10 a.
The amount of 100 liters / 10a was applied to the foliage of the weeds with a small sprayer. Three weeks after the treatment, the weeding effect of the weeds was investigated according to the above-mentioned examination criteria, and the results are shown in Table 4.

[0112]

[Table 36]

[0113] A plastic pot having a surface area of 250 cm ² was filled with upland soil, and seeds of Abutilon and Indica were used as weeds and seeded with 0.5 cm of soil. The next day, the diluting solution of the wettable powder shown in Example 5 was uniformly sprayed on the soil cover so that the amount of the active ingredient was 200 g per 10 a, and 20 days after the treatment, the herbicidal effect was investigated and the results were evaluated. It is shown in Table 5.

[0114]

[Table 37]

   ─────────────────────────────────────────────────── ─── Continued front page    (72) Inventor Masami Furuguchi             2-2-1 Otemachi, Chiyoda-ku, Tokyo Date             Main Soda Co., Ltd. (72) Inventor Kazunari Kato             345 Takada, Odawara-shi, Kanagawa Nippon Soda Co., Ltd.             Company Odawara Research Center F-term (reference) 4H011 AB01 BA01 BB09 BC03 BC07                       BC18 DA02 DA15 DA16 DC01                       DC05 DC06 DD03 DD04

Claims (5)

[Claims] 1. A general formula (1): (In the formula, R1 is a halogen atom, a C _1-6 alkyl group, a C _3-6
Cycloalkyl group, C _1-6 haloalkyl group, C _1-6 alkoxy, C _3-6 cycloalkoxy group, C _1-6 haloalkoxy group, C _1-6 alkylamino group, C _1-6 halo alkyl group, Represents a di-C _1-6 alkylamino group, a hydroxyl group or an amino group, and R 2 and R 3 are each independently a C _1-6 alkyl group, C
_3-6 cycloalkyl group or C _1-6 haloalkyl group, R 4 represents hydrogen atom, C _1-4 alkyl group, C _1-4 alkoxy group or hydroxyl group, X represents halogen atom, C _1-4 alkyl group, C _3-6 cycloalkyl group, C _1-3 haloalkyl group, C _1-4 alkoxy group, C
_1-3 haloalkoxy group, cyano group, nitro group, phenyloxy group optionally substituted by A, C _1-4 alkoxycarbonyl group, mono C _1-4 alkylcarbamoyl group, or di C _1-4 alkylcarbamoyl group Represents a group, A represents a halogen atom, a C _1-4 alkyl group, a C _1-4 alkoxy group, a C _1-4 haloalkyl group, a nitro group, or a cyano group, and n represents 0 or an integer of 1 to 5. Represent ) The pyrimidine compound or its salt represented by these. 2. A general formula (2): (In the formula, R2 represents a C _1-6 alkyl group, a C _3-6 cycloalkyl group, or a C _1-6 haloalkyl group, and L ₁ and L ₂ each independently represent a leaving group.) The compound represented by the general formula (3): (In the formula, R4 represents a hydrogen atom, a C _1-4 alkyl group, a C _1-4 alkoxy group, or a hydroxyl group, and R3 represents a C _1-6 alkyl group, a C _3-6 cycloalkyl group, or a C _3-6 cycloalkyl group. _1-6 represents a haloalkyl group, X represents a halogen atom, a C _1-4 alkyl group, a C _3-6 cycloalkyl group, a C _1-3 haloalkyl group, a C _1-4 alkoxy group, C
_1-3 haloalkoxy group, cyano group, nitro group, phenyloxy group optionally substituted by A, C _1-4 alkoxycarbonyl group, mono C _1-4 alkylcarbamoyl group, or di C _1-4 alkylcarbamoyl group Represents a group, A represents a halogen atom, a C _1-4 alkyl group, a C _1-4 alkoxy group, a C _1-4 haloalkyl group, a nitro group, or a cyano group, and n represents 0 or an integer of 1 to 5. Represent ) And a compound represented by the general formula (4): (In the formula, R2, R3, R4, L ₁ , X and n have the same meanings as described above), and a step of obtaining the compound represented by the general formula (4) Formula (5) R5H (5) (In the formula, R5 is a C _1-6 alkoxy group, a C _3-6 cycloalkoxy group, a C _1-6 haloalkoxy group, a C _1-6 alkylamino group, C _{A 1-6} haloalkylamino group, a diC _1-6 alkylamino group, a hydroxyl group, or an amino group).
-1) (In the formula, R2, R3, R4, R5, X and n have the same meanings as described above.) A method for producing a pyrimidine compound. 3. A general formula (6): (In the formula, R 6 is a C _1-6 alkyl group, a C _3-6 cycloalkyl group, a C _1-6 haloalkyl group, a C _1-6 alkoxy group, a C _3-6
Represents a cycloalkoxy group, a C _1-6 haloalkoxy group or a di-C _1-6 alkylamino group, R 2 represents a C _1-6 alkyl group, a C _3-6 cycloalkyl group or a C _1-6 haloalkyl group Represents ) And a compound represented by the general formula (7): (In the formula, R7 is a hydrogen atom, a C _1-4 alkyl group, or
_{Represents a} C _1-4 alkoxy group, R 3 represents a C _1-6 alkyl group, C _3-6 cycloalkyl group or C _1-6 haloalkyl group, X represents a halogen atom, C _1-4 alkyl group, C _3-6 cycloalkyl group, C _1-3 haloalkyl group, C _1-4 alkoxy group, C
_1-3 haloalkoxy group, cyano group, nitro group, phenyloxy group optionally substituted by A, C _1-4 alkoxycarbonyl group, mono C _1-4 alkylcarbamoyl group, or di C _1-4 alkylcarbamoyl group Represents a group, A represents a halogen atom, a C _1-4 alkyl group, a C _1-4 alkoxy group, a C _1-4 haloalkyl group, a nitro group, or a cyano group, and n represents 0 or an integer of 1 to 5. Represent ) And a compound represented by the general formula (1-2) having a step of reacting in the presence of a dehydration condensing agent. (In the formula, R2, R3, R6, R7, X and n have the same meanings as described above.) A method for producing a pyrimidine compound represented by the formula. 4. The pyrimidine compound or a salt thereof according to claim 1, wherein the compound represented by the general formula (1) is an optically active substance. 5. A herbicide containing, as an active ingredient, one or more pyrimidine compounds represented by the general formula (1) or salts thereof.