JPH0525143A - 3-phenyluracil derivative and herbicide - Google Patents

Abstract

PURPOSE:To provide a new 3-phenyluracil derivative useful as a herbicide exhibiting selectivity to important crops and having excellent herbicidal effect on various kinds of weeds at a low rate of application. CONSTITUTION:The compound of formula I [R<1> is NR<6>R<7> or OR<8> (R<6> to R<8> are H or 1-4C alkyl); R<2> is 1-6C alkyl or CF3; R<4> is H or halogen; R<5> is halogen or NO2; D<1> is H, halogen, CO2R<9> R<9> is H or 1-6C alkyl), OR<10> (R<10> is R<9>, 3-6C alkenyl, 3-6C alkynyl or 3-6C cycloalkyl), OCHR<11>CO2R<12>, SCHR<11>CO2R<12> (R<11> is H or 1-3C akyl; R<12> is H or 1-4C alkyl) or NHCO2R<13> (R<13> is 1-6C alkyl, phenyl or benzyl)], e.g. 1-amino-3-(4-chloro-2-fluorophenyl)-6trifluoromethyl-2,4(1 H,3H)-phrimidinedione. The compound of formula I wherein R<1> is NH2 can be produced by reacting a compound of formula II with a compound of formula III and aminating the 1-position of the uracil ring of the resultant compound of formula IV.

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to a novel 3-phenyluracil derivative and a selective herbicide containing the derivative as an active ingredient.

[0002]

2. Description of the Related Art Conventionally, many herbicides have been put into practical use in order to protect important crops such as rice, soybean, wheat, corn, cotton and beet from weeds and to enhance the productivity of these important crops. . However, there is still a need for new and better herbicides. That is, those having a high herbicidal effect at a low dose (especially, it is necessary to kill weeds by spraying as low a dose as possible from the viewpoint of environmental protection) and those having an appropriate residual effect (in recent years,
It has been a problem that drugs with long soil residue damage subsequent crops, and it is important to show appropriate residual effect after spraying. ), Those which kill weeds immediately after spraying (sowing and transplanting of the next crop in a short period after the chemical treatment), those with few chemical treatments (complex weeds for farmers). It is important to reduce the number of times of control work as much as possible.), A wide range of weed control objects (broad leaf weeds, grass weeds, perennial weeds, etc.) Chemicals that can control these are desirable.), Those with many application methods (more powerful herbicidal effect can be obtained by combining soil treatment effect, foliage treatment effect, etc.) Those that do not exist (preferably those that can selectively kill only weeds in arable land where crops and weeds are mixed) and those that have high safety (low human toxicity and low crop residue are preferred. ) Is desired .

On the other hand, it is known that a specific compound of the uracil derivative exhibits herbicidal activity, for example, The Pesticide Manual No. 8
Edition, p. 89, The British Crop Protection Council
Bromacil is described as one of the herbicides having a uracil skeleton in the Council) (1987) and the like. In addition, JP-A-63-107967, JP-A-63-41466, and JP-A-61-221178.
U.S. Pat. No. 3,869,457, U.S. Pat. No. 39
No. 81715 and WO 88/10254 disclose uracil derivatives having a herbicidal action.

[0004]

In view of such circumstances, the present inventors have shown that the herbicides exhibiting selectivity for important crops and having excellent herbicidal effect against many weeds at low doses. As a result of continuing research to develop

[0005]

[Chemical 4]

[Wherein R ¹ is NR ⁶ R ⁷ (R ⁶ and R
Each ⁷ independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. ) Or OR ⁸ (R ⁸ represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms),
R ² represents an alkyl group having 1 to 6 carbon atoms or a trifluoromethyl group, R ⁴ represents a hydrogen atom or a halogen atom, R ⁵ represents a halogen atom or a nitro group, D ¹ represents a hydrogen atom or a halogen atom. , CO ₂ R ⁹ (R ⁹
Represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. ), OR ¹⁰ (R ¹⁰ is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 3 to 6 carbon atoms, an alkynyl group having 3 to 6 carbon atoms, or a cycloalkyl having 3 to 6 carbon atoms. Represents a group), OCHR ¹¹ CO ₂ R
¹² (R ¹¹ represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, R ¹² represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms), SCHR ¹¹ CO ₂ R ¹² (R ¹¹ and R ¹² has the same meaning as described above.), NHCHR ¹¹ C
O ₂ R ¹² (R ¹¹ and R ¹² have the same meanings as described above) or NHCO ₂ R ¹³ (R ¹³ has 1 to 6 carbon atoms.
Represents an alkyl group, an optionally substituted phenyl group or an optionally substituted benzyl group on the phenyl ring. )
Represents ] The 3-phenyluracil derivative represented by the following (hereinafter, referred to as the compound of the present invention) is remarkably strong herbicidal activity against many weeds in any of soil treatment, soil admixture treatment and foliage treatment. In addition, the present invention has been completed by finding out that it has high safety against wheat, corn, cotton, soybean, beet, rice and the like which are important crops.

Next, the substituents R ¹ , R ^{2 of} the compound of the present invention,
Specific examples of R ⁴ , R ⁵ and D ¹ are given below. As R ¹ , amino group, methylamino group, ethylamino group, n-propylamino group, iso-propylamino group, tert-butylamino group, dimethylamino group, hydroxyl group, methoxy group, ethoxy group, n-propoxy group, iso -Propoxy group and n
Examples thereof include butoxy group and the like, and amino group is preferable.

R ² is trifluoromethyl group, methyl group, ethyl group, n-propyl group, iso-propyl group, n-
Examples thereof include a butyl group, an iso-butyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, a neo-pentyl group and an n-hexyl group, preferably a trifluoromethyl group,
Examples thereof include methyl group, ethyl group, n-propyl group and iso-propyl group.

R^FourAs hydrogen atom, fluorine atom, chlorine source
And a bromine atom and an iodine atom, preferably water.
Examples include elementary atom, fluorine atom and chlorine atom. R^FiveWhen
Nitro group, fluorine atom, chlorine atom, bromine atom and iodine
Elemental atoms include, preferably chlorine atom and bromine atom.
Can be given. D¹Is a hydrogen atom. Furthermore
To D¹Is CO₂R⁹If R⁹Is a hydrogen atom, methyl
Group, ethyl group, n-propyl group, iso-propyl group,
n-butyl group, iso-butyl group, sec-butyl group,
tert-butyl group, n-pentyl group, neo-plier
Group and n-hexyl group. D¹Is OR
^TenIf R^TenAs a hydrogen atom, methyl group, ethyl
Group, n-propyl group, iso-propyl group, n-butyl
Group, iso-butyl group, sec-butyl group, tert-
Butyl group, n-pentyl group, neo-pentyl group, n-
Hexyl group, cyclopropyl group, cyclobutyl group, cyclo
Lopentyl group, cyclohexyl group, allyl group, 1-methyl
Ru-2-propenyl group, propargyl group and 1-methyl
2-propynyl group and the like, preferably n-p
Ropyl group, iso-propyl group, cyclopentyl group,
Examples include ropagyl group and 1-methyl-2-propynyl group.
To be D¹Is OCHR¹¹CO₂R¹², SCHR¹¹CO
₂R¹²Or NHCHR¹¹CO ₂R¹²If R¹¹age
Hydrogen atom, methyl group, ethyl group, n-propyl group and
And an iso-propyl group, R¹²As hydrogen source
Child, methyl group, ethyl group, n-propyl group, iso-group
Examples include a ropyl group and an n-butyl group. D¹Is N
HCO₂R¹³If R¹³As a methyl group, an ethyl group,
n-propyl group, iso-propyl group, n-butyl group,
tert-butyl group, n-pentyl group, neo-plier
Group, n-hexyl group, and optionally substituted phenyl group
(Examples of the substituent include a methyl group, a fluorine atom, and a chlorine atom.
To be ) And an optionally substituted benzyl group (substitution
Examples of the group include methyl group, fluorine atom and chlorine atom.
It ) Is given. D¹Is a halogen atom, halo
As the gen atom, fluorine atom, chlorine atom, bromine atom and
Iodine atoms are included.

The structural characteristics of the compound of the present invention are uracil
NR in the 1st position of the ring⁶R⁷Or OR⁸And has
R as a substituent on the 3-position benzene ring of the ring^Four, R^FiveAnd
And D ¹To have a unique combination of. this thing
As a result, the compounds of the present invention are highly permeable and highly herbicidal.
Have activity. As a result, the compound of the present invention is a conventional herbicide.
Compared to, the soil treatment for various weeds including perennial weeds
It can be applied to any method of treatment and foliage treatment,
And shows a high effect quickly despite low-dose application
In addition, it has a great feature that it also has an appropriate residual effect.
Have.

The compounds of the present invention can be synthesized, for example, by the methods shown in Schemes 1-2 (R ¹ in Schemes 1-2,
R ² , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ and D ¹ have the same meanings as described above, G ¹ represents an alkyl group having 1 to 4 carbon atoms, and G ² represents the number of carbon atoms. Represents an alkyl group having 1 to 4 or a phenyl group, and R ′ represents an alkyl group having 1 to 4 carbon atoms or a phenyl group. ).

[0012]

[Chemical 5]

(1) In Scheme 1, as a first step, β-aminoacrylic acid ester (V) is reacted with N-phenylcarbamate (VII) to give a uracil derivative (I '), and (I') is isolated. The following is a method for producing a uracil derivative (I) by aminating the 1-position of the uracil ring as the second step after or without isolation. First step reaction Usually, 0.5 to 1.5 equivalents of (VII) with respect to (V), preferably 0.1.
Use 8 to 1.2 equivalents.

The reaction usually requires a solvent, and as the solvent, aliphatic hydrocarbons such as hexane, heptane, ligroin, petroleum ether, aromatic hydrocarbons such as benzene, toluene, xylene, chlorobenzene, chloroform, methylene chloride, etc. Halogenated hydrocarbons, diethyl ether,
Dioxane, ethers such as tetrahydrofuran, acetone, ketones such as methyl ethyl ketone, acetonitrile, nitriles such as isobutyronitrile, pyridine, N,
Tertiary amines such as N-diethylaniline, N, N-dimethylacetamide, N, N-dimethylformamide, N-
Acid amides such as methylpyrrolidone, dimethyl sulfoxide, sulfur-containing compounds such as sulfolane, alcohols such as methanol, ethanol, propanol, butanol, water and mixtures thereof, and the like, preferably the above-mentioned aliphatic hydrocarbons, aromatic Examples thereof include group hydrocarbons, acid amides, sulfur-containing compounds and mixtures thereof.

Usually, 0.5 to 10 equivalents, preferably 1.0 to 3.0 equivalents of base are used with respect to (V). Pyridine as a base,
Triethylamine, N, N-dimethylaniline, N, N-diethylaniline, 4- (N, N-dimethylamino) pyridine, 1,
4-diazabicyclo [2.2.2] octane and other nitrogen-containing organic bases, sodium hydride, potassium hydride, sodium hydroxide, potassium hydroxide, sodium carbonate, inorganic bases such as potassium carbonate, sodium methoxide, sodium ethoxide, Metal alcoholates such as potassium tert-butoxide, metal alkyl mercaptides such as sodium methyl mercaptide and sodium ethyl mercaptide, and inorganic bases such as sodium hydride and metal alcoholates such as sodium methoxide are preferable. To be

The reaction temperature is generally 0 to 200 ° C., preferably room temperature to the reflux temperature of the reaction mixture. The reaction time is usually 10 minutes to 72 hours, preferably 30 minutes to 24 hours. After completion of the reaction, (I ′) can be isolated by acidifying with a mineral acid such as hydrochloric acid or an organic acid such as acetic acid, trifluoroacetic acid or p-toluenesulfonic acid.

The aminating agent is preferably added in an amount of 0.5 to 5.0 equivalents relative to the second step (I ′).
Use 0.8 to 2.0 equivalents. Examples of the aminating agent include phenoxyamines such as 2,4-dinitrophenoxyamine, sulfonylhydroxyamines such as O-mesitylenesulfonylhydroxyamine and O-p-toluenesulfonylhydroxyamine, and chloramine.

The reaction usually requires a solvent, and as the solvent, aliphatic hydrocarbons such as hexane, heptane, ligroin, petroleum ether, aromatic hydrocarbons such as benzene, toluene, xylene, chlorobenzene, chloroform, methylene chloride, etc. Halogenated hydrocarbons, diethyl ether,
Dioxane, ethers such as tetrahydrofuran, acetone, ketones such as methyl ethyl ketone, acetonitrile, nitriles such as isobutyronitrile, pyridine, N,
Tertiary amines such as N-diethylaniline, N, N-dimethylacetamide, N, N-dimethylformamide, N-
Examples include acid amides such as methylpyrrolidone, sulfur-containing compounds such as dimethyl sulfoxide and sulfolane, alcohols such as methanol, ethanol, propanol and butanol, and mixtures thereof, preferably the above aromatic hydrocarbons and acid amides. , Sulfur-containing compounds and mixtures thereof.

Usually, 0.5 to 10 equivalents, preferably 1.0 to 3.0 equivalents of base are used with respect to (I '). Pyridine as a base,
Triethylamine, N, N-dimethylaniline, N, N-diethylaniline, 4- (N, N-dimethylamino) pyridine, 1,
4-diazabicyclo [2.2.2] octane and other nitrogen-containing organic bases, sodium hydride, potassium hydride, sodium hydroxide, potassium hydroxide, sodium carbonate, inorganic bases such as potassium carbonate, sodium methoxide, sodium ethoxide, Examples thereof include metal alcoholates such as potassium tert-butoxide, metal alkylmercaptides such as sodium methyl mercaptide and sodium ethyl mercaptide, and inorganic bases such as sodium hydride and potassium carbonate are preferable.

The reaction temperature is usually -30 to 200 ° C, preferably
It is carried out at a temperature of -10 ° C to the reflux temperature of the reaction mixture. The reaction time is usually 10 minutes to 72 hours, preferably 30 minutes to 24 hours.

[0021]

[Chemical 6]

(2) In Scheme 2, N-phenylacetoacetamide (X) is ring-closed as an oxazine derivative (XI) as the first step, and after (XI) is isolated or not isolated, As the second step, a method for producing a uracil derivative (I) by reacting with hydrazines or hydroxyamines will be described. The reaction of the first step usually requires a solvent, and as the solvent, aliphatic hydrocarbons such as hexane, heptane, ligroin, petroleum ether, aromatic hydrocarbons such as benzene, toluene, xylene, chlorobenzene, chloroform, methylene chloride, etc. Halogenated hydrocarbons such as pyridine, tertiary amines such as pyridine and N, N-diethylaniline, acid amides such as N, N-dimethylacetamide, N, N-dimethylformamide and N-methylpyrrolidone, dimethyl sulfoxide , Sulfur-containing compounds such as sulfolane, organic acids such as formic acid, acetic acid, butyric acid, acetic anhydride, and mixtures thereof, preferably aliphatic hydrocarbons, aromatic hydrocarbons, halogenated hydrocarbons and Examples include organic acids.

The reaction temperature is generally 0 to 200 ° C., preferably room temperature to the reflux temperature of the reaction mixture. The reaction time is usually 10 minutes to 72 hours, preferably 30 minutes to 24 hours. 0.5 to 10 equivalents of hydrazines or hydroxylamines relative to the second stage oxazine derivative (XI), preferably 0.8
Use ~ 3 equivalents. Examples of hydrazines include hydrazine or methylhydrazine, ethylhydrazine, tert-butylhydrazine, and alkylhydrazines such as 1,1-dimethylhydrazine.Examples of hydroxylamines include hydroxyamine or methoxyamine, ethoxyamine, and isopropoxyamine. Alkoxy amines are listed.

The reaction proceeds even without solvent, but it is usually promoted by using a solvent. Hexane as a solvent, heptane, ligroin, aliphatic hydrocarbons such as petroleum ether, benzene, toluene, xylene, aromatic hydrocarbons such as chlorobenzene, chloroform, halogenated hydrocarbons such as methylene chloride, diethyl ether, dioxane, Ethers such as tetrahydrofuran, acetone, ketones such as methyl ethyl ketone, acetonitrile, nitriles such as isobutyronitrile, pyridine, N,
Tertiary amines such as N-diethylaniline, N, N-dimethylacetamide, N, N-dimethylformamide, N-
Acid amides such as methylpyrrolidone, dimethyl sulfoxide, sulfur-containing compounds such as sulfolane, alcohols such as methanol, ethanol, propanol, butanol, water and mixtures thereof, and the like, preferably the above-mentioned aliphatic hydrocarbons, aromatic Examples thereof include group hydrocarbons, ethers, alcohols, halogenated hydrocarbons, acid amides, sulfur-containing compounds and mixtures thereof.

The reaction temperature is usually from -30 to 150 ° C, preferably from -10 ° C to the reflux temperature of the reaction mixture. The reaction time is usually 10 minutes to 96 hours, preferably 30 minutes to 48 hours. Hereinafter, the synthesis examples of the compound of the present invention and the intermediate will be specifically described as Examples, but the present invention is not limited thereto.

[Reference Example] Synthesis of 3- (4-chloro-2-fluoro-5-isopropoxycarbonylphenyl) -6-trifluoromethyl-2,4 (1H, 3H) -pyrimidinedione (intermediate)

[0027]

[Chemical 7]

To a suspension of 0.89 g of sodium hydride (oil, purity 55%) and 50 ml of dimethylformamide,
A solution of ethyl 3-amino-4,4,4-trifluorocrotonate (3.73 g) and toluene (30 ml) was added dropwise at 0 ° C over 15 minutes. After completion of dropping, the mixture was stirred at 0 ° C for 15 minutes and then -30
After cooling to 0 ° C, a solution of 4-chloro-2-fluoro-5-isopropoxycarbonylphenyl isocyanate 5.0 g and toluene 30 ml was added dropwise over 20 minutes. After completion of dropping, the mixture was stirred at room temperature for 1 hour.

The solvent was distilled off under reduced pressure, and the obtained oily product was mixed with water (4).
00 ml was added, acidified with concentrated hydrochloric acid, and extracted twice with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried over anhydrous sodium sulfate, the solvent was evaporated, and the obtained crude product was purified by silica gel column chromatography (developing solvent chloroform: ethyl acetate = 5: 1). Then, 2.9 g of the target compound was obtained as a glass.

¹ H-NMR (CDCl ₃ ) δ (ppm): 1.32 (6H, d, J
= 6Hz), 4.95-5.56 (1H, m), 6.15 (1H, s), 7.23 (d, J = 9H
z), 7.74 (d, J = 8Hz), 8.24 (1H, br s)

Example 1 1-Amino-3- (4-chloro-2-fluoro-5-isopropoxycarbonylphenyl) -6-trifluoromethyl-2,4 (1H, 3
H) -Pyrimidinedione (Compound No. 1)

[0032]

[Chemical 8]

3- (4-chloro-2-fluoro-5-isopropoxycarbonylphenyl) -6-trifluoromethyl-2,4 (1H, 3H) -pyrimidinedione 0.
To a mixture of 8 g, 0.28 g of anhydrous potassium carbonate and 4 ml of N, N-dimethylformamide, 0.4 g of 2,4-dinitrophenoxyamine was added at room temperature, and the mixture was stirred overnight. Ethyl acetate was added, water, saturated aqueous sodium hydrogen carbonate solution,
Washed with saturated saline and dried over anhydrous sodium sulfate,
The ethyl acetate was distilled off, and the resulting crude product was purified by preparative thin layer chromatography (developing solvent chloroform: ethyl acetate = 20: 1) to give the target compound 0.3.
8 g was obtained as a glass.

¹ H-NMR (CDCl ₃ ) δ (ppm): 1.34 (6H, d, J
= 6Hz), 4.72 (2H, s), 4.89-5.51 (1H, m), 6.21 (1H, s),
7.44 (1H, d, J = 10Hz), 7.88 (1H, d, J = 8Hz)

Example 3 1-Amino-3- (4-chloro-2-fluorophenyl) -6-trifluoromethyl-2,4 (1H, 3H) -pyrimidinedione (Compound N
o. 2) Synthesis

[0036]

[Chemical 9]

3- (4-chloro-2-fluorophenyl) -6-trifluoromethyl-2,4 (1H, 3H)
-Pyrimidinedione (0.50 g, 1.62 mmol), anhydrous potassium carbonate (0.22 g, 1.62 mmol) and N, N-dimethylformamide (2 ml) were mixed at room temperature with 2,2-dinitrophenoxyamine (0.32 g, 1.2). (62 mmol) was added and the mixture was stirred overnight. After distilling off N, N-dimethylformamide, the product was dissolved in ethyl acetate, washed with water, saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous sodium sulfate, and distilled off ethyl acetate to give a crude product. Crystals were obtained. This was washed with diethyl ether to obtain 0.32 g of the desired product (yield 61.5%) as reddish brown crystals.

Melting point 216-218 ° C. ¹ H-NMR (d ₆ -DMSO) δ (ppm): 5.24 (2 H, br s), 6.16 (1
H, s), 6.92-7.56 (3H, m)

Example 4 Synthesis of 3- (4-chloro-3-isopropoxycarbonylphenyl) -6-trifluoromethyl-2,4 (1H, 3H) -pyrimidinedione (Compound No. 3)

[0040]

[Chemical 10]

It was synthesized according to the above-mentioned example. Melting point 152-154 ° C ¹ H-NMR (CDCl ₃ ) δ (ppm): 1.36 (6H, d, J = 6Hz), 4.61
(2H, br s), 4.98-5.41 (1H, m), 6.25 (1H, s), 7.11-7.
79 (3H, m) The compounds of the present invention synthesized according to the above schemes or Examples are shown in Tables 1 and 2 including the compounds synthesized in the above Examples, but the present invention is not limited thereto. Not a thing.

Table 1

[0043]

[Chemical 11]

[0044]

[0045]

[0046]

[0047]

[0048]

[0049]

[0050]

[0051]

[Chemical 12]

[0052]

[Chemical 13]

[0053]

The application dose of the compound of the present invention varies depending on the application scene, application time, application method, target weeds, cultivated crops, etc., but generally 0.0001 to 10 kg per hectare (ha) as an active ingredient amount, Preferably 0.001-
About 5kg is appropriate. The compound of the present invention is a herbicide of other species, various insecticides, fungicides during formulation or spraying, if necessary.
You may mix and apply with a plant growth regulator, a synergist, etc.

In particular, by applying it in combination with another herbicide, it is possible to expect a lower cost due to a decrease in the amount of the applied drug, a broader herbicidal spectrum due to the synergistic action of the mixed drugs, and a higher herbicidal effect. At this time, it is possible to combine a plurality of known herbicides at the same time. The types of herbicides used in combination with the compound of the present invention include, for example, the compounds described in Farm Chemicals Handbook, 1990 edition.

In particular, when the compound of the present invention is applied to soybean, preferred agents to be mixed with the compound of the present invention include trifluralin, pendimethalin, alachlor, metolachor. , Metribuzin, linuron, chlorimur-ethyl
on ethyl), imazaquin, imazethapyr (i
mazethapyr), dinoceb (dinoseb), bifenox (b
ifenox), clomazone, etc.

In applying the compound of the present invention as a herbicide, generally, a suitable carrier, for example, solid carrier such as clay, talc, bentonite, diatomaceous earth and white carbon, or water, alcohols (isopropanol,
Butanol, benzyl alcohol, furfuryl alcohol, etc.), aromatic hydrocarbons (toluene, xylene, etc.),
Ethers (anisole, etc.), ketones (cyclohexanone, isophorone, etc.), esters (butyl acetate, etc.),
It can be applied by mixing it with a liquid carrier such as acid amides (N-methylpyrrolidone etc.) or halogenated hydrocarbons (chlorobenzene etc.), and if desired, a surfactant, an emulsifier, a dispersant, a penetrant, a spreading agent. Glue, thickener, antifreeze,
It can be put into practical use in any dosage form such as a liquid agent, an emulsion, a wettable powder, a dry flowable agent, a flowable agent, a powder agent and a granule by adding an anti-caking agent and a stabilizer.

Next, formulation examples of preparations using the compound of the present invention will be shown concretely. However, the compounding examples of the present invention are not limited to these. In the following formulation examples, "part" means part by weight. [Wettable powder] Compound of the present invention ─────── 5-80 parts Solid carrier ─────── 10-85 parts Surfactant ─────── 1-10 parts Others ─── ──── Examples of 1 to 5 parts and others include anti-caking agents.

[Emulsion] Compound of the present invention ─────── 1 to 30 parts Liquid carrier ─────── 30 to 95 parts Surfactant ─────── 5 to 15 parts [Flowable] Agent] Compound of the present invention ─────── 5-70 parts Liquid carrier ─────── 15-65 parts Surfactant ─────── 5-12 parts Others ────── -Other than 5 to 30 parts, for example, antifreezing agents, thickeners and the like can be mentioned.

[Granular wettable powder (dry flowable agent)] Compound of the present invention ─────── 20-90 parts Solid carrier ─────── 10-60 parts Surfactant ─────── 1-20 parts [Granule] Compound of the present invention ─────── 0.1-10 parts Solid carrier ─────── 90〜99.99 parts Other ─────── 1-5 parts [Formulation Example 1] Wettable powder Compound of the present invention (product of Example 2): 50 parts Sieglite PFP ───────── 43 copies (Kaolin clay: product name of Siglite Industrial Co., Ltd.) Solpol 5050 ───────── Part 2 (Anionic surfactant: Toho Chemical Industry Co., Ltd. trade name) Lunox 1000 C ──────── Part 3 (Anionic surfactant: Toho Chemical Industry Co., Ltd. trade name) Carplex # 80 (anti-caking agent)-2 parts (White carbon: Shionogi Pharmaceutical Co., Ltd. product name) The above is uniformly mixed and pulverized to obtain a wettable powder.

[Formulation Example 2] Emulsion Compound of the present invention (product of Example 2) ─── 3 parts xylene ───────── 76 parts Isophorone ───────── 15 parts Solpol 3005X ─ ────── 6 parts (mixture of nonionic surfactant and anionic surfactant: trade name of Toho Chemical Industry Co., Ltd.) The above components are uniformly mixed to form an emulsion.

[Formulation Example 3] Flowable agent Compound of the present invention (product of Example 3) --- 35 parts Agrisol S-711 ──────── 8 parts (Nonionic surfactant: Kao Corporation trade name) Lunox 1000 C ──────── 0.5 part (Anionic surfactant: Toho Chemical Industry Co., Ltd. trade name) 1% Rhodopol water ──────── 20 copies (Thickener: Loan Poulin's trade name) Ethylene glycol (antifreeze) ── 8 parts Water ──────── 28.5 copies The above is uniformly mixed to obtain a flowable agent.

[Formulation Example 4] Granular wettable powder (dry flowable agent) Compound of the present invention (product of Example 2) ─── 75 parts Isoban No. 1 ───────── 10 parts (anionic interface Activator: Kuraray Isoprene Chemical Co., Ltd. product name Vanillex N ───────── 5 parts (Anionic surfactant: Sanyo Kokusaku Pulp Co., Ltd. product name) Carplex # 80 ────── 10 parts (white carbon: trade name of Shionogi Pharmaceutical Co., Ltd.) The above is uniformly mixed and pulverized to obtain a dry flowable agent.

[Formulation Example 5] Granule Compound of the present invention (product of Example 2) ── 0.1 part Bentonite ─────── 55.0 parts Talc ──────── 44.9 parts The above are uniformly mixed and ground. After that, a small amount of water is added, and the mixture is kneaded with stirring, granulated by an extrusion granulator, and dried to give granules.

In use, the above-mentioned wettable powder, emulsion, flowable powder and granular wettable powder are diluted 50 to 1000 times with water so that the active ingredient is 0.0001 per hectare (ha).
Sprinkle so that it becomes 10kg. The compound of the present invention can be used as a herbicide for upland fields in any treatment method such as soil treatment, soil admixture treatment, and foliage treatment. As the field weeds (Cropland weeds) targeted by the compound of the present invention,
For example, Solanaceae weeds represented by Solanum nigrum , Datura stramonium , and Abutilon theophrast.
i ), American stag deer ( Side spinosa ), etc., Malvaceae weeds, Malaba morning glory ( Ip
Convolvulaceae weeds, such as morning glory ( Ipomoea spps.) and bindweed ( Calystegia spps.), such as omoea purpurea, and Amaranthus l.
ividus), Amaranthaceae (Amaranthaceae) weeds typified by slender amaranth (Amaranthus retroflexus), etc., cocklebur (Xa
nthium pensylvanicum ), ragweed ( Ambrosia artemis )
iaefolia ), sunflower ( Helianthus annuu ), syringa ( Galinsoga ciliat) , spiny thistle ( Cirsi)
um arvense) , Noboguro chrysanthemum ( Senecio vulgaris ), Himejon ( Erigeron annus )
ositae) Weeds, Pepper ( Rorippa indica ), Field Pepper ( Sinapis arvensis ), Raspberry ( Capsella Bursa )
pastris) Brassicaceae represented by such (Cruciferae) weeds, knotweed (Polygonum Blumei), wild buckwheat (Polygo
Polygonacea (Polygonacea) represented by num convolvulus )
e) weed, purslane family represented by purslane (Portulaca oleracea), etc. (Portulacaceae) weed common lambsquarters (Ch
enopodium album ), koa kaza ( Chenopodium ficifoli )
um ), Hochigi ( Kochia scoparia ), and other weeds of the family Chenopodiaceae, and Stellaria me
Caryophyllaceae typified by dia )
Weeds, Scrophulariaceae weeds such as Veronica persica, Weeds of Commelinaceae typified by Commelina communis , Lamium amplexi
caule), Lamium purpureum (Lamium purpureum) Labiatae represented by such (Labiatae) weeds, Konishikisou (Eu
phorbia supina ), Hypericum ( Euphorbia macula)
Euphorbiaceae represented by ta), etc. (Euphorbiaceae) weeds, thorns without cleavers (Galium spurium), cleavers (Galium aparine), madder (Rubia akane) Rubiaceae represented by such (Rubiaceae) weeds, violets (Viola
arvensis ) and other weeds (Violaceae) weeds, legumes (Leguminosae) weeds (Leguminosae) typified by weeds ( Sesbania exaltata ) and Ebisugusa ( Cassia obtusifolia ), etc. Broad-leaved wee
ds), wild sorghum ( Sorgham bicolor) , giant millet ( Panicum dichotomiflorum ), Johnson grass ( So
rghum halepense ), barnyard grass ( Echinochloa crus-gal
li), crabgrass (Digitaria adscendens), oats (Avena fatua), goosegrass (Eleusine indica), green foxtail (Setaria viridis), foxtail (Alopecurus aegualis) grass weeds (Graminaceous weeds typified by, etc.), purple nutsedge (Cyperus rotundu
s , Cyperus esculentus ) and the like, and Cyperaceous weeds.

Further, the compound of the present invention can be used as a herbicide for paddy field in any treatment method of soil treatment under flooded water and foliage treatment. Examples of paddy weeds include paddy weeds ( Alisma canaliculatu).
m ), Modassus ( Sagittaria trifolia ), Urikawa ( S
agittaria pygmaea ), etc.
ataceae) weeds, Cyperus difformis ,
Cyperus serotinus , Firefly ( Scirp )
us juncoides ), Elegocharis kuroguwa
i ) Cyperaceae weeds typified by E. , etc., Scrothulariaceae weeds represented by Lindemia pyxidaria , Monochor
ia vaginalis ) and other species of water mallow (Potender
iaceae) weeds, hilus white ( Potamogeton distinctus )
Such as, for example, weeds (Potamogetonaceae), weeds (Lythraceae), represented by Rotala indica , Echinochloa ( Echinochloa )
crus-galli ) and other grass weeds (Gramineae).

Further, the compound of the present invention is a defoliant.
Is also useful as The compound of the present invention can be applied to the control of various weeds in non-agricultural fields such as sports fields, open spaces, and track ends, as well as agricultural and horticultural fields such as upland fields, paddy fields and orchards. Next, the usefulness of the compound of the present invention as a herbicide will be specifically described in the following test examples. [Test Example 1] Herbicidal effect test by soil treatment Put sterilized diluvial soil in a plastic box having a length of 15 cm, a width of 22 cm, and a depth of 6 cm, and put Nobye, Mejiba, Cyperus japonicus, Pinegrass, Prickly pear, Pepper, rice,
Mixed sowing of corn, wheat, soybean and cotton, about 1 cm
After covering with soil, small amounts of spray were uniformly sprayed onto the soil surface so that the amount of active ingredient was a predetermined ratio. As a drug solution for spraying, a formulation appropriately adjusted according to the above-mentioned formulation example or the like was diluted with water and used. Three weeks after spraying the chemical solution, the herbicidal effect on various weeds and crops was investigated according to the following criteria. The results are shown in Table 3.

Criteria 5: Herbicidal rate 90% or more (almost complete death) 4-Heralicidal rate 70-90% 3-Hericidal rate 40-70% 2-Hericidal rate 20-40% 1-Hericidal rate 5-20% 0 -Hericidal rate 5% or less (almost no effect) However, the above-mentioned herbicidal rate is obtained by judging the above-ground weed weight of the chemical treatment area and the above-ground weed weight of the untreated area by the following formula. is there. Herbicide rate = [1-above-ground fresh grass weight of treated area / above-ground fresh grass weight of untreated area] x 100 [Test Example 2] Herbicidal effect test by foliage treatment 15 cm long, 22 cm wide, 6 cm deep made of plastic Put the sterilized diluvial soil in the box, and then, Nobye, Crabgrass, Cyperaceae, dogwood, syringa, dog pepper, rice,
Seeds of corn, wheat, soybean, cotton, and beet were sown in spots, and the soil was covered by about 1 cm. When various plants reached the 2-3 leaf stage, the active ingredients were sprayed evenly on the foliage so that the amount of the active ingredient became a predetermined ratio.

As the drug solution for spraying, a formulation appropriately adjusted according to the above-mentioned formulation example or the like was diluted with water and used, and this was sprayed on the entire surface of the foliage of various weeds with a small spray. Four weeks after spraying the chemical solution, the herbicidal effect on various weeds and crops was investigated according to the criteria of Test Example-1. The results are shown in Table 4. The compound No. in each table is the compound No. in the examples.
And the symbols have the following meanings.

[0070] N (Novier), M (Mexico), K (Cyperus vulgaris), H (European sea bass), D (Beetle), I (Purple), R (Rice), T (Maize), W (Wheat), S ( Soybean), C (cotton), B
(beat)

[0071]                           Table 3 ────────────────────────────   Compound dose     No. (g / ha) N M K H D I R T W S C ────────────────────────────     1 10 5 5 5 5 5 5 5 3 2 1 2 ────────────────────────────     2 10 5 5 5 5 5 5 2 3 0 3 3 ────────────────────────────

[0072]                           Table 4 ─────────────────────────────   Compound dose     No. (g / ha) N M K H D I R T W S C B ─────────────────────────────     1 10 5 5 5 5 5 5 5 5 5 5 5 5 ─────────────────────────────     2 10 5 3 5 5 5 5 1 2 0 5 5 5 ─────────────────────────────

   ─────────────────────────────────────────────────── ─── Continued front page    (72) Inventor Kaoru Ito             1 Nissan Chemical, 722, Tsuboi-cho, Funabashi, Chiba             Central Research Institute (72) Inventor Hiroshi Kita             1 Nissan Chemical, 722, Tsuboi-cho, Funabashi, Chiba             Central Research Institute (72) Inventor Tsutomu Namaki             1470 Shiraoka, Shirooka-cho, Minami-Saitama-gun, Saitama             Gaku Kogyo Co., Ltd. Biological Science Laboratory (72) Inventor Shigenomi Watanabe             1470 Shiraoka, Shirooka-cho, Minami-Saitama-gun, Saitama             Gaku Kogyo Co., Ltd. Biological Science Laboratory (72) Inventor, Kimihiro Ishikawa             1470 Shiraoka, Shirooka-cho, Minami-Saitama-gun, Saitama             Gaku Kogyo Co., Ltd. Biological Science Laboratory

Claims (4)

[Claims] 1. Formula (I): [In the formula, R ¹ is NR ⁶ R ⁷ (R ⁶ and R ⁷ each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms) or OR ⁸ (R ⁸ is a hydrogen atom or a carbon atom number) R 4 represents an alkyl group of 1 to 4), R ² represents an alkyl group having 1 to 6 carbon atoms or a trifluoromethyl group, R ⁴ represents a hydrogen atom or a halogen atom, and R ^4
5 represents a halogen atom or a nitro group, D ¹ represents a hydrogen atom, a halogen atom, CO ₂ R ⁹ (R ⁹ represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms), OR
¹⁰ (R ¹⁰ is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms,
It represents an alkenyl group having 3 to 6 carbon atoms, an alkynyl group having 3 to 6 carbon atoms, or a cycloalkyl group having 3 to 6 carbon atoms. ), OCHR ¹¹ CO ₂ R ¹² (R ¹¹ represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and R ¹² represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms), SCHR ¹¹ CO ₂ R ¹² (R ¹¹ and R ¹² have the same meanings as described above), NHCHR ¹¹ CO ₂ R ¹² (R
¹¹ and R ¹² have the same meanings as described above. ) Or NH
CO ₂ R ¹³ (R ¹³ represents an alkyl group having 1 to 6 carbon atoms, a phenyl group which may be substituted or a benzyl group which may be substituted by a phenyl ring). ] The 3-phenyl uracil derivative represented by these. 2. Formula (I): [Wherein R ¹ , R ² and D ¹ have the same meanings as described above, R ⁴ represents a hydrogen atom, a fluorine atom or a chlorine atom,
R ⁵ represents a chlorine atom. ] The 3-phenyl uracil derivative of Claim 1 represented by these. 3. Formula (I): [Wherein R ¹ , R ² and D ¹ have the same meanings as described above, R ⁴ represents a hydrogen atom, a fluorine atom or a chlorine atom,
R ⁵ represents a bromine atom. ] The 3-phenyl uracil derivative of Claim 1 represented by these. 4. A herbicide containing the 3-phenyluracil derivative according to claim 1.