JPH08104678A - Pyrimidine-4-one derivative and herbicide containing the same - Google Patents

Abstract

PURPOSE: To obtain a hovel compound capable of expressing excellent herbicidal activity in an extraordinarily low drug concentration and excellent in crop- selectivity and useful as herbicides.

CONSTITUTION: The pyrimidine-4-one derivatives are compounds expressed by formula I [R¹ is H, a phenyl or the like; R², R⁴, R⁵ and R⁷ are each H or a lower alkyl; R³ is H, a lower alkenyl or the like; W is O or NR⁶ (R⁶ is H, a lower alkynyl or the like)], e.g. 2-(6-methyl-4-oxo-5-phenyl-(3H)- pyrimidine-3-yl)-2-methyl-3'-trifluormethyl-propioanilide. The compound is obtained, e.g., by reacting a compound of formula II with a compound of the formula: R⁷C(OR⁸)₃ (R⁸ is CH₃ or C₂H₅) in a solvent such as toluene or the like at 90-160°C or to the boiling point of the solvent. The compound of formula II used as the raw material is obtained, e.g. by reacting a compound of formula III with a compound of formula IV and successively reacting the reaction product with ammonia in the solvent.

COPYRIGHT: (C)1996,JPO

Description

Detailed Description of the Invention

[0001]

The present invention relates to a novel pyrimidine-4
And a herbicide containing the same.

[0002]

BACKGROUND OF THE INVENTION As a pyrimidin-4-one derivative,
JP-A-59-106472 discloses 3-alkyl-5-
The herbicidal activity of phenyl-pyrimidin-4 (3H) -one derivatives is disclosed.

[0003]

However, these known compounds have a drawback that they are not always sufficient in herbicidal effect and crop selectivity.

An object of the present invention is to provide a pyrimidin-4-one derivative having herbicidal activity which is more excellent in herbicidal effect and crop selectivity than conventional compounds, and a herbicide containing the same.

[0005]

The present inventors have synthesized various novel pyrimidine-4-one derivatives, and have diligently studied their physiological activities.
The present invention has been completed by discovering compounds that exert herbicidal activity against various weeds without damaging useful crops from on-derivatives, and completed the present invention.

That is, the present invention provides the following general formula (I)

[0007]

Embedded image

[In the formula, R ¹ represents a hydrogen atom, an optionally substituted phenyl group, a lower alkyl group or an aralkyl group. R ² represents a hydrogen atom or a lower alkyl group. R ³ represents a hydrogen atom, an optionally substituted phenyl group, a lower alkyl group, a lower alkenyl group or a lower alkynyl group. R
⁴ and R ⁵ each independently represent a hydrogen atom or a lower alkyl group. W represents an oxygen atom or NR ⁶ . R ⁶ represents a hydrogen atom, a lower alkyl group, a lower alkenyl group or a lower alkynyl group. R ⁷ represents a hydrogen atom or a lower alkyl group. ] It is related with the pyrimidin-4-one derivative represented by these, and the herbicide containing it.

Next, the pyrimidin-4-one derivative represented by the general formula (I) of the present invention will be described in more detail.

R ¹ in the above general formula (I) of the present invention,
Specific examples of the groups in the definitions of R ² , R ³ , R ⁴ , R ⁵ , R ⁶ and R ⁷ will be described below.

Halogen atom: Fluorine, chlorine, bromine or iodine atom.

Lower alkyl group; carbon number such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, neopentyl, tert-pentyl, hexyl group, etc. There may be mentioned 1 to 6 linear or branched lower alkyl groups.

Lower alkenyl groups; eg allyl, 2
1 to 5 carbon atoms such as -methyl-2-propenyl, 2-butenyl, 3-butenyl, 3-methyl-2-butenyl group
Lower alkenyl groups of

Lower alkynyl group; for example, 2-propynyl, 1-methyl-2-propynyl, 2-butynyl, 3
There may be mentioned lower alkynyl groups having 1 to 5 carbon atoms such as butynyl.

Lower alkoxy group; for example, methoxy,
Examples thereof include lower alkoxy groups such as ethoxy, propoxy, isopropoxy, butoxy and pentoxy groups, which contain the above lower alkyl groups as an alkyl moiety.

Lower alkylthio group; for example, lower alkylthio group containing the lower alkyl group as an alkyl moiety such as methylthio, ethylthio, propylthio, isopropylthio, butylthio, pentylthio group and the like.

Lower alkylsulfonyl group; for example, lower alkylsulfonyl group containing the lower alkyl group as an alkyl moiety such as methylsulfonyl, ethylsulfonyl, propylsulfonyl, isopropylsulfonyl, butylsulfonyl, pentylsulfonyl group and the like. .

Lower haloalkyl group; for example, bromomethyl, difluoromethyl, dichloromethyl, trifluoromethyl, 1-chloroethyl, 2-iodoethyl, 3-
Chloropropyl, 2-methyl-2-chloropropyl,
1,2 carbon atoms such as 2,2,2-trifluoroethyl group
To lower haloalkyl groups of 4 can be mentioned.

Lower haloalkoxy groups; for example, the above haloalkyl groups such as trifluoromethoxy, difluoromethoxy, chlorodifluoromethoxy, 2-chloroethoxy, 1,1,2,2-tetrafluoroethoxy, 3-chloropropoxy and the like. Can be mentioned as a lower haloalkoxy group.

Alkoxycarbonyl group: For example, an alkoxycarbonyl group having about 2 to 8 carbon atoms such as methoxycarbonyl, ethoxycarbonyl, isopropoxycarbonyl group and the like can be mentioned.

Alkoxycarbonylalkoxy group; for example, methoxycarbonylmethoxy, 1- (methoxycarbonyl) ethoxy, 1- (ethoxycarbonyl) ethoxy, 1-methyl-3- (isopropoxycarbonyl).
An alkoxycarbonylalkoxy group having about 3 to 10 carbon atoms such as a propyl group can be mentioned.

Acyl group; for example, an acyl group such as acetyl, propionyl, butyryl, isobutyryl and the like can be mentioned.

Aralkyl groups; eg benzyl, 1-
Phenylethyl, 2-phenylethyl, 1-methyl-1
-Phenylethyl, 1-methyl-2-phenylethyl,
Examples thereof include 1-ethyl-2-phenylethyl and 3-phenylpropyl groups.

A phenyl group which may be substituted; a phenyl group, and the phenyl group is a halogen atom, a hydroxy group,
Lower alkyl group, lower alkoxy group, phenoxy group, lower alkylthio group, lower alkylsulfonyl group, lower haloalkyl group, lower haloalkoxy group, lower alkoxymethyl group, lower alkylthiomethyl group, aralkyloxy group, aralkylthio group, phenylthiomethyl Group, a phenyl group, an alkoxycarbonyl group, an alkoxycarbonylalkoxy group, an acyl group, a cyano group, a nitro group, a phenyl group and the like are shown, and specific examples of the optionally substituted phenyl group include: Phenyl,
3-fluorophenyl, 3-chlorophenyl, 3,5-
Dichlorophenyl, 3-trifluoromethylphenyl,
3-toluyl, 2,5-xylyl, 3-anisyl, 3-
Phenoxyphenyl, 3-methylthiophenyl, 2-chloro-5- (methylsulfonyl) phenyl, 3- (trifluoromethyl) phenyl, 3,5-bis (difluoromethoxy) phenyl, 3-methoxycarbonylphenyl, 3- (1 -Methoxycarbonyl) ethoxyphenyl, 3-nitrophenyl, 3-cyanophenyl, 3-acetylphenyl, 2-chloro-5-nitrophenyl,
3,5-dichlorophenyl, 2-fluoro-4-chlorophenyl, 2,5-dichlorophenyl, 3,5-dichloro-4-methylphenyl group and the like can be mentioned.

Further, groups not specifically shown in the above groups may be optionally combined with the atoms and groups already mentioned,
Alternatively, it is selected according to commonly known common sense.

Of these substituents, preferable ones as R ¹ are phenyl group, 2-fluorofer group, 2-chlorophenyl group and 2-methylphenyl group. R ² is a hydrogen atom, a methyl group or an ethyl group. R
³ is a phenyl group, a mono-substituted phenyl group substituted at the 3-position, and a 2-substituted phenyl group substituted at the 2,5-position or the 3,5-position. Preferred as R ⁴ and R ⁵ is a methyl group or an ethyl group. R ⁶ is preferably a hydrogen atom or a methyl group. Preferred as R ⁷ is a hydrogen atom.

Further preferred compounds of the invention of formula (I) are:
The following general formula (I-1)

[0028]

[Chemical 4]

[Wherein X ¹ , X ² and X ³ are each independently a hydrogen atom, a halogen atom, a lower alkyl group, a lower alkoxy group, a lower alkylthio group, a phenoxy group, a lower haloalkyl group or a lower haloalkoxy group. Etc. ]
Is a compound represented by.

The above-mentioned general formula (I) provided by the present invention
Specific examples of the compound of the present invention represented by are shown in Table 1. The abbreviations used in the tables in this description have the following meanings.

Me; methyl group Et; ethyl group Pr; n-propyl group iPr; isopropyl group Bu; n-butyl group iBu; isobutyl group sBu; sec-butyl group tBu; tert-butyl group Hex; hexyl group Ph; phenyl Group Bn; benzyl group; no substituent

[0032]

[Table 1]

[0033]

[Table 2]

[0034]

[Table 3]

[0035]

[Table 4]

[0036]

[Table 5]

[0037]

[Table 6]

[0038]

[Table 7]

[0039]

[Table 8]

[0040]

[Table 9]

[0041]

[Table 10]

[0042]

[Table 11]

[0043]

[Table 12]

[0044]

[Table 13]

The compound of the general formula (I) in the present invention may be obtained by any method, and can be produced, for example, by the following method.

The compound (I) of the present invention is obtained by reacting the compound represented by the formula (II) with the compound represented by the formula (III) in a suitable solvent or in a large excess of (III). be able to.

[0047]

Embedded image

[Wherein R ¹ , R ² , R ³ , R ⁴ , R ⁵ ,
R ⁶ and R ⁷ have the same meaning as defined in the general formula (I). R ⁸ represents a Me or Et group. The reaction temperature can be arbitrarily set within the range of 90 ° C. to 160 ° C. or the boiling point of the solvent. When the solvent is used, any solvent may be used as long as it does not react with the raw materials, but a solvent having a high boiling point such as toluene, xylene or mesitylene is preferable in view of the reaction temperature. Although the reaction time varies depending on the set conditions, it can be usually completed in 1 to 6 hours.

The product (I) can be isolated from the reaction mixture by a conventional method and can be easily purified by recrystallization, column chromatography or the like.

The compound of the general formula (II) may be obtained by any method, for example, it can be produced by the following method. However, the present invention is not limited to those manufactured by this method.

Compound (II) can be obtained, for example, by Chem. Pharm. B.
ull. Vol. 32 (1984) 3848 and the like, or a method similar thereto or the like, and can be obtained by reacting compound (IV) with ammonia in a suitable solvent.

[0052]

[Chemical 6]

[In the formula, R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ⁶ have the same meanings as defined in the general formula (I). The reaction temperature can be arbitrarily set within the range of 90 ° C. to 160 ° C. or the boiling point of the solvent. When the solvent is used, any solvent may be used as long as it does not react with the raw materials, but a solvent having a high boiling point such as toluene, xylene or mesitylene is preferable in view of the reaction temperature. Although the reaction time varies depending on the set conditions, it can usually be completed in 1 to 360 minutes.

The compound (II) can be used in the next reaction without isolation and purification.

The compound (IV) can be obtained by reacting the compound represented by the formula (V) with the compound represented by the formula (VI) in a suitable solvent or without a solvent.

[0056]

[Chemical 7]

[Wherein R ¹ , R ² , R ³ , R ⁴ , R ⁵ ,
And W have the same meaning as defined in the general formula (I). The reaction temperature can be arbitrarily set within the range of 90 ° C. to 160 ° C. or the boiling point of the solvent. When the solvent is used, any solvent may be used as long as it does not react with the raw materials, but a solvent having a high boiling point such as toluene, xylene or mesitylene is preferable in view of the reaction temperature. The reaction time varies depending on the set conditions, but it can be usually completed in 1 to 240 minutes.

The product (IV) can be isolated from the reaction mixture by a conventional method, and can be easily purified by recrystallization, column chromatography or the like.

The product (IV) can be used in the next reaction without isolation.

The compounds of the general formulas (V) and (VI) can be obtained by a method known per se or a production method analogous thereto.

The compound represented by the formula (IV) is described in JP-A-57 / 57
It can also be synthesized by a method similar to the method described in -98275.

The compound (VI) is prepared by reacting the amino acid derivative represented by the general formula (VII) with thionyl chloride in an ether solvent such as tetrahydrofuran, and then reacting with the general formula (VIII).
It can be produced by reacting with the aniline derivative of.

[0063]

Embedded image

The reaction temperature is 0 for both the first and second steps.
C. to 50.degree. C. is convenient. The reaction time for both the first stage and the second stage is about 6 hours to 2 days.

The product (VI) can be isolated from the reaction mixture by a conventional method and can be easily purified by recrystallization, column chromatography or the like.

Compound (VI) can be used in the next reaction without isolation and purification.

The compound of the present invention represented by the general formula (I-3) is obtained by reacting the compound of the present invention represented by the general formula (I-2) with a compound represented by the general formula (IX) in the presence of a base. Can be manufactured.

[0068]

[Chemical 9]

[Wherein R ¹ , R ² , R ⁴ , R ⁵ and R ⁷
Represents the same meaning as defined in the general formula (I).
Y represents an oxygen atom or NR ³ . R ³ has the same meaning as defined in the general formula (I). R ⁹ represents a primary or secondary lower alkyl group, lower alkenyl group or lower alkynyl group. Z is a halogen atom, a p-toluenesulfonyloxy group, a methylsulfonyloxy group,
Trifluoromethylsulfonyloxy group or formula OS
It represents a group such as O ₂ R ^{11 which} is easily eliminated in a nucleophilic reaction. The reaction temperature is conveniently from room temperature to about 140 ° C. or the boiling point of the solvent. Any solvent may be used as long as it is inert under the reaction conditions. For example, aprotic polar solvents such as N, N-dimethylformamide, dimethylsulfoxide, acetonitrile and acetone, and ether solvents such as tetrahydrofuran and dioxane. ,methanol,
Examples thereof include alcohols such as ethanol, and mixed solvents of these with water. Examples of the base include inorganic carbonates such as potassium carbonate, potassium hydrogen carbonate, sodium carbonate and sodium hydrogen carbonate, inorganic bases such as sodium hydroxide and potassium hydroxide, sodium methoxide and sodium hydride. Separation and purification of the resulting compound of the formula (I-3) of the present invention from the reaction mixture can be carried out by a method known per se, for example, extraction, recrystallization, chromatography and the like.

The compound of the present invention represented by the general formula (I-5) can be produced by alkaline hydrolysis of the compound of the present invention represented by the general formula (I-4).

[0071]

[Chemical 10]

[Wherein R ¹ , R ² , R ³ , R ⁴ , R ⁵ ,
R ⁷ has the same meaning as defined in the general formula (I). As the alkali, for example, an aqueous solution of sodium hydroxide, potassium hydroxide or the like can be used. The solvent may be water and any solvent that is inert under these reaction conditions, but examples thereof include alcohols such as methanol and ethanol and ethers such as tetrahydrofuran and dioxane. The reaction temperature is preferably room temperature to about 80 ° C. Separation and purification of the resulting compound of formula (I-5) from the reaction mixture can be carried out by a method known per se, for example, extraction, recrystallization, chromatography and the like.

The compound of the present invention represented by the general formula (I) is a compound of the present invention represented by the general formula (I-5):
(Carbon tetrachloride and triphenylphosphine) or thionyl chloride, and then reacted with a compound represented by the general formula (X) in the presence of a base.

[0074]

[Chemical 11]

[Wherein R ¹ , R ² , R ³ , R ⁴ , R ⁵ ,
R ⁷ and W have the same meaning as defined in the general formula (I). The reaction temperature is conveniently room temperature to about 140 ° C. or the boiling point of the solvent in the first step reaction, and ice cooling to about 60 ° C. in the second step. The solvent may be any as long as it is inert under the reaction conditions, for example, halogenated hydrocarbon solvents such as carbon tetrachloride, chloroform and methylene chloride, hydrocarbon solvents such as toluene, xylene and mesitylene, diethyl ether. Examples of the solvent include ether solvents such as tetrahydrofuran, dimethoxyethane, and the like. Examples of the base include tertiary amines such as triethylamine, diisopropylethylamine and pyridine, and inorganic bases such as sodium hydroxide and sodium carbonate. In some cases, these bases may be used in the form of an aqueous solution, or may be used by previously forming a salt with the compound of the formula (X). When the compound of formula (X) is an amine, it may be used in excess as a base. Separation and purification of the resulting compound of the present invention of formula (I) from the reaction mixture can be carried out by a method known per se, for example, extraction, recrystallization, chromatography and the like.

The compound of the present invention represented by the general formula (I) is the compound of the present invention represented by the general formula (I-5):
It can also be produced by reacting with a dehydrating condensing agent such as carbonyldiimidazole or dicyclohexanecarbodiimide, and then reacting with a compound represented by the general formula (X) or a salt thereof.

[0077]

[Chemical 12]

[Wherein R ¹ , R ² , R ³ , R ⁴ , R ⁵ ,
R ⁷ and W have the same meaning as defined in the general formula (I). ] The reaction temperature is from the ice cooling to about 60 ° C. for the first step reaction,
The second stage is conveniently from room temperature to about 100 ° C. or the boiling point of the solvent. The reaction time is 0.5 to 24 hours.
The solvent may be any as long as it is inert under the reaction conditions, for example, halogenated hydrocarbon solvents such as carbon tetrachloride, chloroform and methylene chloride, hydrocarbon solvents such as toluene, xylene and mesitylene, diethyl ether. Examples thereof include ether solvents such as tetrahydrofuran, dimethoxyethane and the like, ketones such as acetone and methyl ethyl ketone, or aprotic polar solvents such as acetonitrile, N, N-dimethylformamide and N, N-dimethylacetamide. Separation and purification of the resulting compound of the present invention of formula (I) from the reaction mixture can be carried out by a method known per se, for example, extraction, recrystallization, chromatography and the like.

[0079]

EXAMPLES Next, synthetic examples of the compounds of the present invention will be specifically described with reference to Examples.

Example 1 2- (6-Methyl-4-oxo-5-phenyl- (3H) -pyrimidin-3-yl)-
Preparation of 2-methyl-3'-trifluoromethyl-propioanilide (Compound No. 5) 5-Phenyl-2,2,6-trimethyl-2H, 4H-
1,3-dioxin-4-one (1.78 g) and 2-
Amino-3′-trifluoromethyl-isobutyroanilide (2.0 g) was heated in 40 ml of xylene at 150 ° C., and the solvent was distilled off until the temperature of the distillate became constant.
After completion of the reaction, ammonia gas was passed through the reaction solution at 120 ° C. for 2 hours, and then xylene was distilled off under reduced pressure. 10 ml of triethyl orthoformate was added to the residue, and the mixture was heated under reflux for 2 hours and concentrated under reduced pressure, and the reaction mixture was purified by silica gel chromatography (hexane / ethyl acetate = 1/2) to give the title compound (1.65 g).

Example 2 3 ', 5'-dichloro-2-
(6-methyl-4-oxo-5-phenyl- (3H)-
Preparation of Pyrimidin-3-yl) -2-methyl-propioanilide (Compound No. 7) 5-Phenyl-2,2,6-trimethyl-2H, 4H-
1,3-dioxin-4-one (2.0 g) and 2-amino-3 ′, 5′-dichloro-isobutyroanilide (2.22 g) were heated in 150 ml of xylene at 150 ° C., and a distillate was obtained. The solvent was distilled off until the temperature was constant.
After completion of the reaction, ammonia gas was passed through the reaction solution at 120 ° C. for 2 hours, and then xylene was distilled off under reduced pressure. 10 ml of triethyl orthoformate was added to the residue, and the mixture was heated under reflux for 2 hours and concentrated under reduced pressure, and the reaction mixture was purified by silica gel chromatography (hexane / ethyl acetate = 1/2) to give the title compound (1.85 g).

Example 3 Preparation of 2-amino-3'-trifluoromethyl-isobutyroanilide 2-aminoisobutyric acid (2.08 g) was added to 25 ml of tetrahydrofuran and thionyl chloride was added to the suspension with stirring at room temperature. (2.5 ml) was added and stirred for 24 hours.
3-aminobenztrifluoride (3.5
g) was added and the mixture was stirred at room temperature for 24 hours. The reaction solution was evaporated under reduced pressure, water and methylene chloride were added to the residue, the organic layer was removed, aqueous ammonia was added to the aqueous layer, and methylene chloride was further added to separate the organic layer. The organic layer was dried over magnesium sulfate and then concentrated under reduced pressure to give the desired title compound (5.0 g).

Example 4 Preparation of 2- (2-acetyl-2-phenylacetamino) -2-methylpropioanilide 5-phenyl-2,2,6-trimethyl-2H, 4H-
1,3-dioxin-4-one (2.26 g) and 2-
Aminoisobutyroanilide (1.85 g) was added to xylene 4
It was heated in 0 ml at 150 ° C., and the solvent was distilled off until the temperature of the distillate became constant. The reaction solution was returned to room temperature, and the precipitated crystals were separated by filtration to obtain 2- (2-acetyl-2-phenylacetamido) -2-methylpropioanilide 2.9 g. m. p. 205-209 ° C; ¹ H-N. M. R. _{(DMSO-d 6): 1.42} (3
H, s), 1.44 (3H, s), 2.14 (3H,
s), 4.889 (1H, s), 7.05 (t), 7.
1-7.4 (m), 7.5-7.6, 8.55 (s),
9.30 (s).

Example 5 2- (6-Methyl-4-oxo-5-phenyl- (3H) -pyrimidin-3-yl)-
Preparation of 2-methyl-propioanilide (Compound No. 1) 2- (2-Acetyl-2-phenylacetamino) -2
-Methyl propioanilide 2.65 g in xylene 50 m
Ammonia gas was allowed to flow for 2 hours at 120 ° C. in 1 l, and then xylene was concentrated under reduced pressure. Triethyl orthoformate 15 in the residue
After adding ml, the mixture was heated under reflux for 2 hours and concentrated under reduced pressure, and the reaction mixture was purified by silica gel chromatography (hexane / ethyl acetate = 1/3) to give the title compound (2.0 g).

Table 2 shows the melting points and ¹ H-NMR peak values of the substances produced by these Examples 1 to 5 and the substances produced by the same method.

[0086]

[Table 14]

[0087]

[Table 15]

The herbicide of the present invention contains the novel compound of the general formula (I) as an active ingredient.

When the compound of the present invention is used as a herbicide, it is mixed with a carrier or a diluent, an additive, an auxiliary agent and the like by a known method, and a formulation form usually used as an agricultural chemical, for example, a powder, Granules, wettable powders, emulsions, water solutions,
Used as a flowable agent. Also other pesticides,
For example, it can be used by mixing or using in combination with fungicides, insecticides, acaricides, herbicides, plant growth regulators, fertilizers, soil conditioners and the like.

In particular, by using it in combination with other herbicides, not only the amount of the drug used is reduced and labor saving is achieved, but also the synergistic action of the two drugs broadens the weed spectrum and further enhances the effect. Can be expected.

The carrier or diluent used in the preparation includes solid or liquid carriers which are generally used.

Examples of the solid carrier include clays represented by kaolinite group, montmorillonite group, illite group, polygoskite group and the like, or pyrophyllite, attapulgite, sepiolite, kaolinite, bentonite, vermiculite, mica, talc and the like. Gypsum, calcium carbonate, dolomite, diatomaceous earth,
Other inorganic substances such as magnesium lime, apatite, zeolite, silicic acid anhydride, and synthetic calcium silicate; plant organic substances such as soybean flour, tobacco flour, walnut flour, wheat flour, wood flour, starch, crystalline cellulose; coumarone Examples thereof include synthetic or natural polymer compounds such as resins, petroleum resins, alkyd resins, polyvinyl chloride, polyalkylene glycols, ketone resins, ester gums, cobal gums, dumbamar gums; waxes such as carnauba wax and beeswax, and urea.

Suitable liquid carriers include, for example, paraffinic or naphthenic hydrocarbons such as kerosene, mineral oil, spindle oil and white oil; aromatic hydrocarbons such as xylene, ethylbenzene, cumene and methylnaphthalene; trichloroethylene and monochloro. Chlorinated hydrocarbons such as benzene and orthochlorotoluene; ethers such as dioxane and tetrahydrofuran; ketones such as acetone, methyl ethyl ketone, diisobutyl ketone, cyclohexanone, acetophenone, isophorone; ethyl acetate, amyl acetate, ethylene glycol acetate, diethylene glycol acetate , Esters such as dibutyl maleate and diethyl succinate; methanol, n-hexanol, ethylene glycol, diethylene glycol, cyclohexanol, Alcohols such as emissions benzyl alcohol, ethylene glycol ethyl ether, ether alcohols such as diethylene glycol butyl ether; dimethylformamide, polar solvents or water such as dimethyl sulfoxide.

In addition, emulsification, dispersion, wetting, spreading, spreading, binding, control of disintegration, stabilization of active ingredient of the compound of the present invention,
Surfactants and other auxiliary agents can be used for the purpose of improving fluidity, preventing rust, and preventing freezing.

Examples of the surfactant to be used may be nonionic, anionic, cationic and zwitterionic, but are usually nonionic and / or anionic. Stuff used. Examples of suitable nonionic surfactants include compounds obtained by polymerizing addition of ethylene oxide to higher alcohols such as lauryl alcohol, stearyl alcohol and oleyl alcohol; polymerization addition of ethylene oxide to alkylnaphthols such as butylnaphthol and octylnaphthol. Compounds: compounds obtained by polymerizing addition of ethylene oxide to higher fatty acids such as palmitic acid, stearic acid and oleic acid; higher fatty acid esters of polyhydric alcohols such as sorbitan, and compounds obtained by polymerizing addition of ethylene oxide thereto.

Suitable anionic surfactants include, for example, alkyl sulphate salts such as sodium lauryl sulphate, oleyl alcohol sulphate amine salt, etc., alkyl succinate dioctyl ester sodium, sodium 2-ethylhexene sulphonate and the like. Examples thereof include aryl sulfonates such as sulfonates, sodium isopropylnaphthalene sulfonate, sodium methylenebisnaphthalene sulfonate, sodium lignin sulfonate, and sodium dodecylbenzene sulfonate.

In addition, the herbicides of the present invention have a high content of casein, gelatin, albumin, glue, sodium alginate, carboxymethyl cellulose, methyl cellulose, hydroxyethyl cellulose, polyvinyl alcohol, etc. for the purpose of improving the properties of the preparation and enhancing the effect. A molecular compound and other auxiliary agents can also be used in combination.

The above-mentioned carriers and various auxiliary agents are appropriately used alone or in combination depending on the purpose, taking into consideration the formulation system of the preparation, the application scene and the like.

The content of the active ingredient of the compound of the present invention in the various dosage forms thus obtained varies depending on the dosage form, but is usually 0.1 to 99% by weight, preferably 1 to 80% by weight. % Is the most suitable.

In the case of a wettable powder, for example, the active ingredient compound is usually contained in an amount of 25 to 90%, and the balance is a solid carrier and a dispersion wetting agent, and a protective colloid agent, a defoaming agent and the like are added if necessary. .

In the case of granules, for example, the active ingredient compound is usually contained in an amount of 1 to 35% by weight, and the balance is a solid carrier and a surfactant. The active ingredient compound is uniformly mixed with the solid carrier, or is uniformly fixed or adsorbed on the surface of the solid carrier, and the particle diameter is about 0.2 to 1.5 mm.

In the case of an emulsion, for example, the active ingredient compound is usually contained in an amount of 5 to 30% by weight, and about 5 to 20% by weight is contained therein.
A weight% emulsifier is contained, and the rest is a liquid carrier, and a spreading agent, an anticorrosive agent and the like are added if necessary.

In the case of a flowable agent, for example, the active ingredient compound is usually contained in an amount of 5 to 50% by weight, which contains about 3 to 10% by weight of a dispersant wetting agent, and the balance is water, and if necessary. Protective colloid agents, preservatives, antifoaming agents and the like are added.

The compound derivative of the general formula (I) of the present invention can be used as a herbicide as the compound itself or in any of the above-mentioned preparation forms.

The composition of the present invention can be applied to various weeds from the pre-emergence period to the growing season, which grow in paddy fields, agricultural lands such as upland fields and non-agricultural lands. The application rate is 1 as the active ingredient amount.
It is about 0.1 to 10,000 g, preferably about 1 to 5,000 g per ha. The application rate can be appropriately selected and changed depending on the type of weed, the growth stage, the place of application, the weather and the like.

Next, several modes of formulation examples using the compound of the present invention will be shown. The "parts" in the following preparations are based on weight.

Formulation Example 1 (Emulsion) Compound No. 2 20 parts xylene 50 parts cyclohexanone 20 parts calcium dodecylbenzene sulfonate 5 parts polyoxyethylene styryl phenyl ether 5 parts The above components were uniformly mixed and dissolved to obtain 100 parts of an emulsion.

Formulation Example 2 (Wettable powder) Compound No. 2 20 parts Clay 70 parts Calcium lignin sulfonate 7 parts Alkylnaphthalene sulfonic acid formalin condensate 3 parts The above components were mixed and ground with a jet mill to obtain 100 parts of a wettable powder.

Formulation Example 3 (Flowable Agent) Compound No. 7 20 parts Sulfosuccinic acid di-2-ethylhexyl ester sodium salt 2 parts Polyoxyethylene nonylphenyl ether 2 parts Defoamer 0.5 parts Propylene glycol 5 parts Water 70.5 parts The above are uniformly pulverized and mixed by a wet ball mill, 100 parts of a flowable agent was obtained.

Herbicides using the compound of the present invention can be prepared according to the above-mentioned preparation examples.

Next, the herbicidal effect of the compound of the present invention will be described with reference to test examples.

Test Example 1 (paddy soil treatment) A 130 cm ² plastic pot was filled with paddy soil,
An appropriate amount of water and a chemical fertilizer were added and kneaded to obtain a paddy field. To this, two rice plants (variety: Koshihikari) which had been grown in a greenhouse so that the number of leaves became two in advance were transplanted as one strain / pot, and furthermore, various types of nobie, konagi, azalea and firefly A certain amount of pups were sowed and flooded at a depth of 3 cm. The next day, a wettable powder was prepared according to Formulation Example 2 and the active ingredient was added for 1 h.
It was diluted with an appropriate amount of water so that the amount per a was 5 kg or 1 kg, and dropped with a pipette. 2 after drug treatment
One day later, the herbicidal effect on each weed and the degree of phytotoxicity to paddy rice were determined according to the following criteria. The results are shown in Table 3.

[0113]

[Table 16]

[0114]

[Table 17]

Test Example 2 (paddy field foliage treatment) A 130 cm ² plastic pot was filled with paddy soil,
An appropriate amount of water and a chemical fertilizer were added and kneaded to obtain a paddy field. 21 rice seedlings (cultivar: Koshihikari), which had been grown in a greenhouse so that the number of leaves would be 2 in advance, were transplanted into each of 21 strains / pot, and various plants such as Nobie, Konagi, Azena and Firefly were further transplanted. A certain amount of pups were sowed and submerged at a depth of 3 cm. After growing Nobie in the greenhouse until the 1.5 leaf stage, a wettable powder is prepared according to Formulation Example 2 and diluted with an appropriate amount of water so that the active ingredient is 5 kg or 1 kg per ha. It was dropped with a pipette. Twenty-one days after the chemical treatment, the herbicidal effect on each weed and the degree of phytotoxicity on rice were determined according to the criteria of Test Example 1. Table 4 shows the results.

[0116]

[Table 18]

[0117]

Industrial Applicability The compounds represented by the above general formula (I) of the present invention are:
As well as exerting an excellent herbicidal effect at extremely low doses over a wide range from the germination to the growing season of annual weeds such as yellow sedge, Azena, Abenome and perennial weeds such as firefly, matsubai, herring mold, cyperus edulis, as well as paddy rice. On the other hand, it has high safety. Further, various weeds that are also problematic in the field, for example, broad-leaved weeds such as Polygonum japonicum, Aobiyu, and Shiloza, perennial and annual perennial Cyperaceae weeds, such as pearl nutsedges, yellow hemlocks, Himekugu, cyperaceae, Kogomegayasuri, weeds, Japanese herb, Enocorogusa, For grass weeds such as Suzumekatabira, Johnson grass, and Poa annua, we show high herbicidal effect by soil treatment or foliar treatment, and at the same time soybean, cotton,
It is characterized by high safety against sugar beet, upland rice, wheat, etc.

Further, it can be used not only in paddy fields and upland fields but also in orchards, mulberry fields, lawns and non-agricultural fields.

Further, when the compound of the present invention is used in combination with a known compound, it shows a complete herbicidal effect against weeds difficult to control with each compound alone, and it is difficult to control with a single agent due to the synergistic herbicidal effect. Effectively control various weeds in various dosages, and paddy rice, soybean, cotton, sugar beet,
It is possible to provide a herbicide that is highly safe for upland rice, wheat, etc. and is very useful in agriculture.

Front page continuation (72) Inventor Yoshihiro Usui 8-3-1 Chuo, Ami-machi, Inashiki-gun, Ibaraki Rhone Poulin Petrochemical Agro Co., Ltd. Ami Research Center (72) Inventor Koichi Araki Chuo, Ami-cho, Inashiki-gun, Ibaraki 8-3-1 Rhone Poulin Petrochemicals Agro Co., Ltd. Ami Research Center (72) Inventor Keiichiro Hayashizaki 8-3-1 Chuo, Ami-cho, Inashiki-gun, Ibaraki Prefecture Rhone Poulin Petrochemicals Agro Co., Ltd. Ami Research Center ( 72) Inventor Takako Aoki 8-3-1 Chuo, Ami-machi, Inashiki-gun, Ibaraki Rhone Poulin Petrochemical Agro Co., Ltd. Ami Research Center (72) Masatoshi Yokoyama 8-3-1 Chuo, Ami-cho, Inashiki-gun, Ibaraki Nu Poulin Petrochemical Agro Co., Ltd. Ami Research Center (72) Inventor Kumiko Inoue 8-3-1 Chuo, Ami-cho, Inashiki-gun, Ibaraki Rho Nu Poulin Petrochemical Agro Co., Ltd. Ami Research Center

Claims (2)

[Claims] 1. A compound of the general formula (I) [In the formula, R ¹ represents a hydrogen atom, an optionally substituted phenyl group, a lower alkyl group or an aralkyl group. R ² represents a hydrogen atom or a lower alkyl group. R ³ represents a hydrogen atom, an optionally substituted phenyl group, a lower alkyl group, a lower alkenyl group or a lower alkynyl group. R ⁴ and R ⁵ each independently represent a hydrogen atom or a lower alkyl group. W represents an oxygen atom or NR ⁶ . R ⁶ represents a hydrogen atom, a lower alkyl group, a lower alkenyl group or a lower alkynyl group.
R ⁷ represents a hydrogen atom or a lower alkyl group. ] The pyrimidin-4-one derivative represented by these. 2. A compound represented by the general formula (I): [In the formula, R ¹ represents a hydrogen atom, an optionally substituted phenyl group, a lower alkyl group or an aralkyl group. R ² represents a hydrogen atom or a lower alkyl group. R ³ represents a hydrogen atom, an optionally substituted phenyl group, a lower alkyl group, a lower alkenyl group or a lower alkynyl group. R ⁴ and R ⁵ each independently represent a hydrogen atom or a lower alkyl group. W represents an oxygen atom or NR ⁶ . R ⁶ represents a hydrogen atom, a lower alkyl group, a lower alkenyl group or a lower alkynyl group.
R ⁷ represents a hydrogen atom or a lower alkyl group. ] The pyrimidine-4-one derivative represented by these is contained as an active ingredient.