JPH0517453A - Uracil derivative and herbicide - Google Patents

Abstract

PURPOSE:To obtain a uracil derivative, capable of exhibiting selectivity for important crops, applicable to various weeds including perennial weeds by either of soil and foliar treatments and developing high quick-acting effects by spraying with an extremely small amount of chemical. CONSTITUTION:A compound expressed by formula I (R<4> is H or halogen; R<5> is halogen; D<26> is 1-4C alkyl or 1-3C haloalkyl), e.g. 3-(4-chloro-3- ethanesulfonylaminophenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)pyrimi dinedione. The aforementioned compound is obtained by reacting, e.g. a beta-aminoacrylic acid ester expressed by formula II (G<1> is 1-4C alkyl) with a phenyl isocyanate expressed by formula III, providing a uracil derivative expressed by formula IV, isolating the resultant compound or, without isolation, methylating the obtained compound with dimethyl sulfate, methyl halides, etc.

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to a novel uracil 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 improve the productivity of these important crops. . These agents can be broadly classified into three categories, upland action, paddy field, and non-arable land, depending on the application scene. Furthermore, in each case, it can be classified into a soil admixture treatment type, a pre-emergence soil treatment type, a post-emergence treatment (stem and leaf treatment) type and the like depending on the application method of the drug.

It is clear that productivity of important crops affects the food economy of each country as the population of the world increases in recent years. With these changes, it is inevitable that the traditional agricultural form will change toward the 21st century. Actually, there is an increasing need for farmers to develop herbicides that can kill or control economically and efficiently weeds that interfere with crop cultivation.

As such a herbicide, the development of a drug having the following conditions has been earnestly desired. Those that have a high herbicidal effect at low doses (especially it is necessary to kill weeds by spraying as low a dose as possible from the viewpoint of environmental protection), those that have an appropriate residual effect (in recent years, soil residue It has been a problem that long drugs damage the succeeding crops, and it is important to show appropriate residual effect after spraying.) Those that kill weeds immediately after spraying (after chemical treatment) , The next crop can be sown and transplanted in a short period of time.), The number of times of chemical treatment is small (it is important for farmers to minimize the number of complicated weed control work), weeds. A broad range of control targets (for broad-leaved weeds, gramineous weeds, perennial weeds, and other weed species with different properties, it is desirable to use a single agent to control these). Combines treatment effects and foliage treatment effects By doing so, a stronger herbicidal effect can be obtained.) Those that do not show harmful chemical damage to crops (those that can selectively kill only weeds in arable land where crops and weeds are mixed) Preferred) is preferred. However, existing herbicides do not meet all of these requirements.

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.

[0006]

In view of such a situation, the present inventors show selectivity for important crops and have excellent herbicidal effect against many weeds with a low dose. As a result of continuing research to develop a herbicide having both soil treatment and foliar treatment, the formula (1)

[0007]

[Chemical 4]

[In the formula, R ⁴ represents a hydrogen atom or a halogen atom, R ⁵ represents a halogen atom, and D ²⁶ represents an alkyl group having 1 to 4 carbon atoms or a haloalkyl group having 1 to 3 carbon atoms. . ] The uracil derivative represented by the following (hereinafter, referred to as the compound of the present invention) was found. The compound of the present invention is structurally characterized in that it has a methyl group at the 1-position of the uracil ring, a trifluoromethyl group at the 6-position of the uracil ring, and R ⁴ and R as substituents on the benzene ring at the 3-position of the uracil ring. ⁵ and NHSO ₂ D ²⁶ .
Therefore, the compound of the present invention has systemic migration and extremely high herbicidal activity. As a result, the compound of the present invention can be applied to various kinds of weeds including perennial weeds in any method of soil treatment and foliage treatment, as compared with conventional herbicides, and has an immediate effect in spite of application of an extremely low dose. It has a great feature that it exerts a highly effective effect and also has an appropriate residual effect.

The compound of the present invention is used as a herbicide for upland fields, paddy fields and non-cultivated lands, regardless of the method of soil treatment or foliage treatment.
American stag deer, Malva morning glory, Inuyuyu, Aobiyu, Onami fir, Ragweed, Sunflower, Toothbrush,
Thistle, thistle, syringa, himejeon, pupa, nuptera, thorns, staghorn, buckwheat,
Broad-leaved, white, black-necked, broom, chickweed, barnyardgrass, communis, quercus chinensis, myrtle, corngrass, red-crowned hornbill, broad-leaved grasses such as yamgra, madder, violet, corngrass, corngrass, corngrass, oleaceae, weeds, weeds , Weedgrass, oat grass, ohoshiba, green foxtail, perennial grass weeds, cyperaceae weeds such as scutellaria, Heraomodaka, Omodaka, Urikakawa, Tamagaya periwinkle, Mizunogiwana, Higurashi swordweed, Aquilegus vulgaris, Spodoptera chinensis, Azuna napus It has high herbicidal activity with low dosage in weeds. Further, it can be safely used for important crops such as wheat, corn, barley, soybean and rice. In particular, for soybean, practically no phytotoxicity is observed in soil treatment and soil admixture treatment. It is highly effective against a large number of weeds such as American hornwort and dogwood, with a low dose showing a high effect.

Further, the compound of the present invention is a defoliant.
Is also useful as The compound of the present invention can be synthesized, for example, by the method shown in Schemes 1 to 7 (Schemes 1 to 7).
R ⁴ , R ⁵ and D ²⁶ have the same meanings as described above, and G
¹ represents an alkyl group having 1 to 4 carbon atoms, G ² represents an alkyl group having 1 to 4 carbon atoms or a phenyl group,
R'represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms or a phenyl group, and Hal represents a halogen atom. ).

[0011]

[Chemical 5]

(1) In Scheme 1, as a first step, β-aminoacrylic acid ester (V) is added to phenyl isocyanate.
The uracil derivative (I ') is reacted with (VI), and after the isolation of (I') or without isolation, the uracil ring 1-position is methylated as the second step to produce the uracil derivative (I). Represents how to do. Reaction of the first step (VI) 0.5 to 1.5 equivalents (VI) relative to (V), preferably 0.1.
Use 8 to 1.2 equivalents.

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-
Examples include acid amides such as methylpyrrolidone, dimethyl sulfoxide, sulfur-containing compounds such as sulfolane, water and mixtures thereof, preferably the above aliphatic hydrocarbons,
Examples thereof include aromatic hydrocarbons, acid amides, sulfur-containing compounds and mixtures thereof.

The reaction proceeds without a base, but usually
0.5 to 10 equivalents, preferably 1.0 to 3.0 equivalents, are used with respect to (V). Pyridine, triethylamine, N, as base
N-dimethylaniline, N, N-diethylaniline, 4- (N, N
-Dimethylamino) pyridine, 1,4-diazabicyclo
[2.2.2] Nitrogen-containing organic bases such as octane, inorganic bases such as sodium hydride, potassium hydride, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium methoxide, sodium ethoxide, potassium te
Examples thereof include metal alcoholates such as rt-butoxide, preferably sodium hydride, sodium hydroxide, potassium hydroxide and potassium carbonate.

The reaction temperature is usually -70 to 200 ° C, preferably -30 ° C to the reflux temperature of the reaction mixture. The reaction time is usually 5 minutes to 72 hours, preferably 10 minutes to 12 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 methylating agent is added in an amount of 0.5 to 10 equivalents, preferably 0.1 to the second step (I ′).
Use 8 to 5.0 equivalents. Examples of the methylating agent include methyl halides such as dimethyl sulfate, methyl chloride, methyl bromide and methyl iodide. 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, tertiary amines such as N, N-diethylaniline,
N, N-dimethylacetamide, N, N-dimethylformamide, acid amides such as N-methylpyrrolidone, sulfur-containing compounds such as dimethyl sulfoxide, sulfolane, water and mixtures thereof, and preferably the above aliphatic carbonization. Hydrogens, aromatic hydrocarbons, ethers, ketones,
Examples thereof include nitrites, acid amides, sulfur-containing compounds and mixtures thereof.

Usually, 0.5 to 10 equivalents, preferably 0.8 to 3.0 equivalents of base are used with respect to (I '). Nitrogen-containing organic bases such as pyridine, triethylamine, N, N-dimethylaniline, N, N-diethylaniline, 4- (N, N-dimethylamino) pyridine, 1,4-diazabicyclo [2.2.2] octane as a base, Examples thereof include inorganic bases such as sodium hydride, potassium hydride, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate and the like, and preferable examples include inorganic bases such as sodium hydride and potassium carbonate.

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.

[0019]

[Chemical 6]

(2) In Scheme 2, 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 methylating 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 and petroleum ether, aromatic hydrocarbons such as benzene, toluene, xylene and chlorobenzene, chloroform, methylene chloride and the like are used. 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, Examples thereof include metal alcoholates such as potassium tert-butoxide, metal alkylmercaptides such as sodium methyl mercaptide and sodium ethyl mercaptide, and inorganic carbonates such as potassium carbonate and sodium hydride, and metal alcoholates such as sodium methoxide. Kind of things.

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.

Second Step Methylation can be carried out under the same reaction conditions as in the second step of Scheme 1.

[0025]

[Chemical 7]

(3) Scheme 3 consists of N-methyl-
This represents a method for producing a uracil derivative (I) by reacting β-aminoacrylic acid ester (VIII) with phenylisocyanate (VI), which can be performed under the same reaction conditions as in Scheme 1.

[0027]

[Chemical 8]

(4) Scheme 4 consists of N-methyl-
This represents a method for producing a uracil derivative (I) by reacting β-aminoacrylic acid ester (VIII) with N-phenylcarbamate (VII), which can be carried out under the same reaction conditions as in Scheme 2.

[0029]

[Chemical 9]

(5) Scheme 5 represents a method for producing the uracil derivative (I) by reacting the amino compound (IX) with a sulfonyl halide (Xa) or a sulfonic anhydride (Xb) as the first step. Normally (IX) to (Xa) or (Xb) 0.3 to 10
Equivalents, preferably 0.5-2.0 equivalents, are used.

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-
Examples thereof include acid amides such as methylpyrrolidone, sulfur-containing compounds such as dimethyl sulfoxide and sulfolane, and a mixture thereof.

The reaction proceeds without a base, but usually (I
Use 0.3 to 10 equivalents relative to X). Moreover, you may use it as a solvent in large excess. Nitrogen-containing organic bases such as pyridine, triethylamine, N, N-dimethylaniline, N, N-diethylaniline, 4- (N, N-dimethylamino) pyridine, 1,4-diazabicyclo [2.2.2] octane as a base, Inorganic bases such as sodium hydride, potassium hydride, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium methoxide, sodium ethoxide,
Examples thereof include metal alcoholates such as potassium tert-butoxide, and preferably the above-mentioned nitrogen-containing organic bases and inorganic bases.

The reaction temperature is usually -30 to 160 ° C, preferably -10 to 130 ° C. The reaction time is usually 10 minutes to 48 hours, preferably 30 minutes to 24 hours.
It takes time.

[0034]

[Chemical 10]

(6) In Scheme 6, as the first step, the amino compound (IX) is reacted with an acylating agent to obtain an acylamino compound (IX-a).
After isolation of (IX-a) or without isolation, the second step is sulfonylation of (IX-a) to give the N-acylsulfamoyl derivative (IX-b), (IX-b ) Is isolated or is not isolated, and is continuously followed by a third step of deacylating (IX-b) to produce a uracil derivative (I).

First Step Reaction Usually, the acylating agent is used in an amount of 0.5 to 5.0 equivalents, preferably 0.8 to 2.0 equivalents, relative to (IX). Examples of the acylating agent include acetyl chloride, benzoyl chloride, acetic anhydride and formic acid, and acetic anhydride is preferable. The reaction proceeds even without solvent, but it is usually promoted by using a solvent. Hexane, heptane, ligroin, petroleum ether and other aliphatic hydrocarbons, benzene, toluene, xylene, chlorobenzene and other aromatic hydrocarbons, chloroform, methylene chloride and other halogenated hydrocarbons, pyridine, N, N -Tertiary amines such as diethylaniline, N, N-dimethylacetamide, N, N-dimethylformamide, acid amides such as N-methylpyrrolidone, sulfur-containing compounds such as dimethyl sulfoxide and sulfolane, formic acid, acetic acid, butyric acid And the like, and mixtures thereof, and preferably the above-mentioned aliphatic hydrocarbons, aromatic hydrocarbons, halogenated hydrocarbons and organic acids.

The reaction proceeds without a base, but usually (I
X) is used in 0.5 to 5.0 equivalents, preferably 0.8 to 2.0 equivalents. Pyridine, triethylamine, N, as base
N-dimethylaniline, N, N-diethylaniline, 4- (N, N
-Dimethylamino) pyridine, 1,4-diazabicyclo
[2.2.2] Nitrogen-containing organic bases such as octane, inorganic bases such as sodium hydride, potassium hydride, sodium hydroxide, potassium hydroxide, sodium carbonate and potassium carbonate, and acetates such as sodium acetate and potassium acetate. To be

The reaction temperature is usually -30 to 200 ° C, preferably 0 to 130 ° C. The reaction time is usually 10 minutes to 24 hours, preferably 30 minutes to 6 hours. Sulfonyl halide (Xa) or sulfonic anhydride (Xb) 0.5 to 5.0 equivalents, preferably 0.8 to 2.0 relative to the second step (IX-a)
Use equivalents.

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-
Examples thereof include acid amides such as methylpyrrolidone, sulfur-containing compounds such as dimethyl sulfoxide and sulfolane, and a mixture thereof.

Usually, 0.5 to 5.0 equivalents, and preferably 0.8 to 2.0 equivalents of the base are used with respect to (IX-a). Pyridine, triethylamine, N, N-dimethylaniline, N, as a base
Nitrogen-containing organic bases such as N-diethylaniline, 4- (N, N-dimethylamino) pyridine, 1,4-diazabicyclo [2.2.2] octane, sodium hydride, potassium hydride, sodium hydroxide, potassium hydroxide Inorganic bases such as sodium carbonate and potassium carbonate, metal alcoholates such as sodium methoxide, sodium ethoxide, potassium tert-butoxide, and the like, and the above nitrogen-containing organic bases and inorganic bases are preferred.

The reaction temperature is usually -30 to 160 ° C, preferably -10 to 130 ° C. The reaction time is usually 30 minutes to 48 hours, preferably 1 to 12 hours. 3rd stage Normal (IX-b) with water and alkali or acid 0.5-3.0
The equivalent is used, preferably 0.8 to 2.0 equivalent. Examples of the alkali include inorganic bases such as sodium hydride, potassium hydride, sodium hydroxide, potassium hydroxide, sodium carbonate and potassium carbonate, and metal alkoxides such as sodium methoxide, sodium ethoxide and potassium tert-butoxide, and preferably. Are the above-mentioned inorganic bases. Examples of the acid include inorganic acids such as hydrochloric acid and sulfuric acid, and organic acids such as acetic acid and trifluoroacetic acid.

The reaction proceeds even without solvent, but it is usually promoted by using a solvent. Hexane, heptane, ligroin, petroleum ether and other aliphatic hydrocarbons, benzene, toluene, xylene, chlorobenzene and other aromatic hydrocarbons, chloroform, methylene chloride and other halogenated hydrocarbons, methanol, ethanol, etc. Alcohols, ethers such as diethyl ether, dioxane and tetrahydrofuran, ketones such as acetone and methyl ethyl ketone, nitriles such as acetonitrile and isobutyronitrile, pyridine, triethylamine, N, N-dimethylaniline, N, N-diethylaniline Such as tertiary amines, N, N-dimethylacetamide, N, N-
Dimethylformamide, acid amides such as N-methylpyrrolidone, organic acids such as formic acid, acetic acid and butyric acid, water and mixtures thereof are preferable, and the above alcohols, ethers, ketones and tertiary amines are preferable. , Acid amides, organic acids and water.

The reaction temperature is usually -30 to 130 ° C, preferably -10 to 100 ° C. The reaction time is usually 10 minutes to 48 hours, preferably 30 minutes to 24 hours.

[0044]

[Chemical 11]

(7) In Scheme 7, as the first step, the amino compound (IX) is sulfonylated to give a disulfonylamino compound (IX-
c), and after or without isolation of (IX-c),
As a second step, (IX-c) is hydrolyzed to give a uracil derivative.
It represents a method for producing (I). First stage 1.0 to 20 equivalents of sulfonyl halide (Xa) or sulfonic anhydride (Xb), preferably 2.0 to 5.0, relative to normal (IX).
Use equivalents.

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-
Examples thereof include acid amides such as methylpyrrolidone, sulfur-containing compounds such as dimethyl sulfoxide and sulfolane, and a mixture thereof.

The reaction proceeds without a base, but usually (I
X) is used in 1.0 to 10 equivalents, preferably 2.0 to 3.0 equivalents. Moreover, you may use it as a solvent in large excess. Nitrogen-containing organic bases such as pyridine, triethylamine, N, N-dimethylaniline, N, N-diethylaniline, 4- (N, N-dimethylamino) pyridine, 1,4-diazabicyclo [2.2.2] octane as a base, Inorganic bases such as sodium hydride, potassium hydride, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate and the like, metal alkoxides such as sodium methoxide, sodium ethoxide, potassium tert-butoxide and the like, and preferably the above And nitrogen-containing organic bases and inorganic bases.

The reaction temperature is usually -30 to 160 ° C, preferably -10 to 130 ° C. The reaction time is usually 30 minutes to 60 hours, preferably 1 to 30 hours. 0.5 to 3.0 equivalents of water, alkali or acid are used, preferably 0.8 to 2.0 equivalents, relative to the second step (IX-c). Examples of the alkali include inorganic bases such as sodium hydride, potassium hydride, sodium hydroxide, potassium hydroxide, sodium carbonate and potassium carbonate, and metal alkoxides such as sodium methoxide, sodium ethoxide and potassium tert-butoxide, and preferably. Are the above-mentioned inorganic bases. Examples of the acid include inorganic acids such as hydrochloric acid and sulfuric acid, and organic acids such as acetic acid and trifluoroacetic acid.

The reaction proceeds even without solvent, but it is usually promoted by using a solvent. Hexane, heptane, ligroin, petroleum ether and other aliphatic hydrocarbons, benzene, toluene, xylene, chlorobenzene and other aromatic hydrocarbons, chloroform, methylene chloride and other halogenated hydrocarbons, methanol, ethanol, etc. Alcohols, ethers such as diethyl ether, dioxane and tetrahydrofuran, ketones such as acetone and methyl ethyl ketone, nitriles such as acetonitrile and isobutyronitrile, pyridine, triethylamine, N, N-dimethylaniline, N, N-diethylaniline ,Four-
(N, N-Dimethylamino) pyridine, tertiary amines such as 1,4-diazabicyclo [2.2.2] octane, N, N-dimethylacetamide, N, N-dimethylformamide, N-
Examples include acid amides such as methylpyrrolidone, organic acids such as formic acid, acetic acid, butyric acid, water and mixtures thereof, preferably the above alcohols, ethers, ketones, tertiary amines, acid amides, Examples include organic acids and water.

The reaction temperature is usually -30 to 160 ° C, preferably -10 to 130 ° C. The reaction time is usually 5 minutes to 48 hours, preferably 30 minutes to 24 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.

[0051]

【Example】

Example 1 Synthesis of 3- (4-chloro-3-ethanesulfonylaminophenyl) -1-methyl-6-trifluoromethyl-2,4 (1H, 3H) -pyrimidinedione (Compound C-5)

[0052]

[Chemical 12]

3- (3-amino-4-chlorophenyl)
-1-Methyl-6-trifluoromethyl-2,4 (1
H, 3H) -pyrimidinedione (0.50 g) was dissolved in pyridine (5 ml) and ethanesulfonyl chloride (0.16 ml) was added at 5 ° C or lower.
Was dripped. After reacting for 2 hours as it was, pyridine was distilled off and the residue was dissolved in ethyl acetate. The extract was washed with water, diluted hydrochloric acid and saturated saline, dried over anhydrous sodium sulfate, and distilled off with ethyl acetate to obtain a crude product. This was washed with diisopropyl ether to obtain 0.37 g of the target compound as light brown crystals.

Example 2 3- (5-acetylamino-
4-chloro-2-fluorophenyl) -1-methyl-6
-Synthesis of trifluoromethyl-2,4 (1H, 3H) -pyrimidinedione (intermediate)

[0055]

[Chemical 13]

2.00 g of 3- (5-amino-4-chloro-2-fluorophenyl) -1-methyl-6-trifluoromethyl-2,4 (1H, 3H) -pyrimidinedione was dissolved in 5 ml of benzene, 0.61 ml of acetic anhydride was added and refluxed for 1 hour. Benzene was distilled off to obtain a crude product, which was washed with hexane to obtain 2.20 g of the objective compound as white crystals. Melting point 263-266 ° C

¹ H-NMR (d ₆ -DMSO) δ (ppm): 2.15 (3H, s), 3.
47 (3H, s), 6.54 (1H, s), 7.70 (1H, d, J = 9Hz), 7.90 (1H, d, J =
8Hz), 9.56 (1H, br s)

Example 3 3- [4-chloro-2-fluoro-5- (N-acetyl) isopropylsulfonylaminophenyl] -1-methyl-6-trifluoromethyl-2,4 (1H, 3H) -Pyrimidinedione (intermediate)
Synthesis of

[0059]

[Chemical 14]

3- (5-acetylamino-4-chloro-
2-Fluorophenyl) -1-methyl-6-trifluoromethyl-2,4 (1H, 3H) -pyrimidinedione 1.
00 g was added at 0 ° C. to a suspension of 0.11 g of sodium hydride in tetrahydrofuran (10 ml), and then 0.30 ml of isopropylsulfonyl chloride was added dropwise. After 2 hours, ice water was added, and the mixture was extracted with ethyl acetate. The ethyl acetate layer is washed with saturated brine, dried over anhydrous sodium sulfate, and then the ethyl acetate is distilled off to give a crude product, which is subjected to preparative thin layer chromatography (developing solvent hexane-ethyl acetate 2 By purifying in 1), 0.54 g of the target compound was obtained as a colorless viscous oil.

¹ H-NMR (CDCl ₃ ) δ (ppm): 1.45 (6H, d, J = 7H
z), 1.97 (3H, s), 3.47 (3H, s), 4.10 (1H, qq, J = 7Hz), 6.23 (1
H, s), 7.29 (1H, d, J = 7Hz), 7.36 (1H, d, J = 9Hz)

Example 4 3- (4-chloro-2-fluoro-5-isopropylsulfonylaminophenyl)-
1-methyl-6-trifluoromethyl-2,4 (1H,
Synthesis of 3H) -pyrimidinedione (Compound C-13)

[0063]

[Chemical 15]

3- [4-chloro-2-fluoro-5-
(N-Acetyl) isopropylsulfonylaminophenyl] -1-methyl-6-trifluoromethyl-2,4
0.47 g of (1H, 3H) -pyrimidinedione was dissolved in 5 ml of tetrahydrofuran, 0.04 g of sodium hydroxide and water of 0.
06 ml was added and reacted for 4 hours. Dilute hydrochloric acid was added to the mixture, extracted with ethyl acetate, washed with water and saturated brine, dried over anhydrous sodium sulfate, and then the ethyl acetate was distilled off to give a crude product, which was subjected to preparative thin layer chromatography (development). Purification with the solvent hexane-ethyl acetate 3: 1) yielded 0.29 g of the desired compound as a colorless viscous oil.

Example 5 3- [5-bis (ethanesulfonyl) amino-2,4-dichlorophenyl] -1-methyl-6-trifluoromethyl-2,4 (1H, 3H)
-Synthesis of pyrimidinedione (intermediate)

[0066]

[Chemical 16]

3- (5-amino-2,4-dichlorophenyl) -1-methyl-6-trifluoromethyl-2,4
To a mixture of (1H, 3H) -pyrimidinedione (1.00 g), triethylamine (0.60 g) and dichloromethane (10 ml) was added ethanesulfonyl chloride (0.56 g) at 5 ° C or lower, and the mixture was stirred overnight. The reaction solution was washed twice with water, then with saturated saline, and dried over anhydrous sodium sulfate. Then, dichloromethane was distilled off to obtain crystals of a crude product. This was washed with diisopropyl ether to obtain 1.40 g of the target compound as pale yellow crystals. Melting point 221-223 ° C

¹ H-NMR (d ₆ -DMSO) δ (ppm): 1.48 (6 H, t, J = 7
Hz), 3.49 (3H, s), 3.61 (4H, q, J = 7Hz), 6.27 (1H, s), 7.56 (1
H, s), 7.67 (1H, s)

Example 6 3- (2,4-dichloro-5)
-Ethanesulfonylaminophenyl) -1-methyl-6
-Synthesis of trifluoromethyl-2,4 (1H, 3H) -pyrimidinedione (Compound C-21)

[0070]

[Chemical 17]

0.80 g of 3- [5-bis (ethanesulfonyl) amino-2,4-dichlorophenyl] -1-methyl-6-trifluoromethyl-2,4 (1H, 3H) -pyrimidinedione was dissolved in 8 ml of dioxane. Then, a solution of 0.12 g of sodium hydroxide (93%) and 2 ml of water was added. After reacting for 4 hours, diluted hydrochloric acid was added to acidify the mixture, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated saline and then dried over anhydrous sodium sulfate. Ethyl acetate was distilled off to obtain a crude product.
This was purified by preparative thin layer chromatography (developing solvent: hexane-ethyl acetate = 3: 2) to obtain 0.46 g of the objective compound as white crystals.

Example 7 3- [5-bis (methanesulfonyl) amino-4-chloro-2-fluorophenyl]
-1-Methyl-6-trifluoromethyl-2,4 (1
Synthesis of (H, 3H) -pyrimidinedione (intermediate)

[0073]

[Chemical 18]

Obtained in the same manner as in Example 5. Melting point 282-
285 ° C ¹ H-NMR (d ₆ -DMSO) δ (ppm): 3.54 (6H, s), 4.22 (3H, s), 6.4
8 (1H, s), 7.79 (1H, d, J = 9Hz), 7.98 (1H, d, J = 7Hz)

Example 8 3- [5-bis (methanesulfonyl) amino-2,4-dichlorophenyl] -1-methyl-6-trifluoromethyl-2,4 (1H, 3H)
-Synthesis of pyrimidinedione (intermediate)

[0076]

[Chemical 19]

Obtained in the same manner as in Example 5. Melting point 300 ° C
Or _{^{1 H-NMR (d 6 -DMSO}} ) δ (ppm): 3.50 (6H, s), 4.20 (3H, s), 6.3
5 (1H, s), 7.55 (1H, s), 7.65 (1H, s)

Example 9 Synthesis of 3- (4-chloro-5-ethylsulfonylamino-2-fluorophenyl) -6-trifluoromethyl-2,4 (1H, 3H) -pyrimidinedione (intermediate)

[0079]

[Chemical 20]

Ethyl 3-amino-4,4,4-trifluorocrotonate (1.06 g, 5.77 mmol) was dissolved in 6.2 ml of N, N-dimethylformamide, and sodium methoxide (0.82) was added.
g (14.4 mmol) was added. After 10 minutes, cool to below 5 ° C, 4
After adding 1.56 g (4.81 mmol) of ethyl -chloro-5-ethylsulfonylamino-2-fluorocarbanilide, the mixture was heated and reacted at 110 ° C for 4 hours. After the reaction, N, N-
After dimethylformamide was distilled off and water was added to dissolve it, the residue was washed 3 times with diethyl ether and adjusted to pH 2 with concentrated hydrochloric acid to precipitate crystals. This was filtered, washed with water, and dried to obtain 1.54 g of the desired compound (yield 77%) as pale yellow crystals. Melting point 190-192 ° C

¹ H-NMR (d ₆ -DMSO) δ (ppm): 1.36 (3H, t, J = 7
Hz), 3.12 (2H, q, J = 7Hz), 6.19 (1H, s), 7.44 (1H, d, J = 9Hz),
7.58 (1H, d, J = 7Hz), 8.86 (1H, br s), 9.20 (1H, br s)

Example 10 3- (4-chloro-5-ethylsulfonylamino-2-fluorophenyl) -1-
Methyl-6-trifluoromethyl-2,4 (1H, 3
H) -Synthesis of pyrimidinediones

[0083]

[Chemical 21]

1.00 g of 3- (4-chloro-5-ethylsulfonylamino-2-fluorophenyl) -6-trifluoromethyl-2,4 (1H, 3H) -pyrimidinedione
(2.41 mmol) was dissolved in 10 ml of acetone, 0.17 g (1.20 mmol) of anhydrous potassium carbonate and 0.23 ml (2.41 mmol) of dimethyl sulfate were added, and the mixture was reacted for 1.5 hours. After distilling off acetone, the residue was dissolved in ethyl acetate, washed with water and saturated brine, dried over anhydrous sodium sulfate, and ethyl acetate was distilled off to obtain a crude product. By recrystallizing this from chloroform-diethyl ether, 0.61 g (yield 59%) of the target compound was obtained as pale yellow crystals. Melting point 176-177 ° C

¹ H-NMR (d ₆ -DMSO) δ (ppm): 1.32 (3H, t, J = 7
Hz), 3.06 (2H, q, J = 7Hz), 3.43 (3H, s), 6.23 (1H, s), 7.29 (1
H, d, J = 9Hz), 7.41 (1H, d, J = 7Hz), 9.11 (1H, br s)

Example 11 3- (4-chloro-5-ethylsulfonylamino-2-fluorophenyl) -6
-Synthesis of trifluoromethyl-2,4 (1H, 3H) -pyrimidinedione (intermediate)

[0087]

[Chemical formula 22]

4-chloro- was added to a mixture of 0.62 g (3.39 mmol) of ethyl 3-amino-4,4,4-trifluorocrotonate, 4 ml of N, N-dimethylformamide and 4 ml of toluene.
Ethyl 5-ethylsulfonylamino-2-fluorophenylcarbanilide 1.00 g (3.08 mmol) and anhydrous potassium carbonate 1.70 g (12.3 mmol) were added, and the mixture was heated to a bath temperature of 130 ° C. The reaction was carried out for 10 hours while removing the distilled toluene. After the reaction, the solvent was distilled off under reduced pressure, and 12 ml of water was added to make an aqueous solution, and 10 ml of 20% hydrochloric acid was added to acidify the solution to precipitate crystals. This was collected by filtration, washed with water, and dried to obtain 1.19 g (yield 93%) of the target compound as pale yellow crystals.

Example 12 3- (4-chloro-5-ethylsulfonylamino-2-fluorophenyl) -1-
Methyl-6-trifluoromethyl-2,4 (1H, 3
H) -Synthesis of pyrimidinediones

[0090]

[Chemical formula 23]

0.50 g of 3- (4-chloro-5-ethylsulfonylamino-2-fluorophenyl) -6-trifluoromethyl-2,4 (1H, 3H) -pyrimidinedione
(1.14 mmol) is dissolved in 5 ml of acetone, 0.12 g (1.43 mmol) of sodium hydrogen carbonate and 0.11 ml (1.14 m
mol) was added and the mixture was heated under reflux for 10 hours. After distilling off acetone, the residue was dissolved in ethyl acetate and washed with water and saturated saline. After drying over anhydrous sodium sulfate, ethyl acetate was distilled off to obtain a crude product. This was recrystallized from chloroform-diethyl ether to give the desired compound 0.45 g (yield 87%).
Was obtained as pale yellow crystals.

Structural formulas and physical properties of the compounds of the present invention synthesized according to the above Examples are shown in Tables 1 and 2 including the above Examples.

[0093]

[Table 1]

[0094]

[Table 2]

[0095]

[Table 3]

[0096]

[Table 4]

[0097]

[Table 5]

The compounds of the present invention synthesized according to the above schemes or Examples are shown in Table 3 including the compounds synthesized in the above Examples, but the present invention is not limited thereto.

[0099]

[Table 6]

[0100]

[Table 7]

[0101]

[Table 8]

In applying the compound of the present invention as a herbicide, generally, a suitable carrier, for example, a solid carrier such as clay, talc, bentonite, diatomaceous earth, white carbon or the like, water, alcohols (isopropanol, butanol, benzyl alcohol, fluroalcohol) are used. Furyl alcohol etc.), aromatic hydrocarbons (toluene, xylene etc.), ethers (anisole etc.), ketones (cyclohexanone, isophorone etc.), esters (butyl acetate etc.), acid amides (N-methylpyrrolidone etc.) ) Or halogenated hydrocarbons (chlorobenzene, etc.) and other liquid carriers can be mixed and applied, and if desired, surfactants, emulsifiers, dispersants, penetrants, spreading agents, thickeners, antifreeze. Agents, anti-caking agents, stabilizers, etc., liquids, emulsions, wettable powders,
It can be put into practical use in any dosage form such as a dry flowable agent, a flowable agent, a powder agent, and a granule agent.

If desired, the compound of the present invention may be mixed and applied with other types of herbicides, various insecticides, fungicides, plant growth regulators, synergists and the like during formulation or spraying. In particular,
By applying it in combination with other herbicides, it is expected that the cost will be reduced by reducing the amount of the applied drug, the herbicidal spectrum will be expanded by the synergistic action of the mixed agents, and a higher herbicidal effect will be expected. At this time, it is possible to combine a plurality of known herbicides at the same time. Examples of the type of herbicide used in combination with the compound of the present invention include, for example, Farm Chemicals Handbook (F
arm Chemicals Handbook) 1990 compound.

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.

The application amount of the compound of the present invention varies depending on the application scene, application time, application method, cultivated crop, etc., but generally 0.0001 to 10 per hectare (ha) as an active ingredient amount.
About kg, preferably about 0.001 to 5 kg is suitable. Next, specific examples of formulation of the preparation when the compound of the present invention is used are shown. 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 to 80 parts Solid carrier ─────── 10 to 85 parts Surfactant ─────── 1-10 parts Other ─────── 1-5 parts Other examples include anti-caking agents.

[Emulsion] Compound of the present invention ─────── 1-30 parts Liquid carrier ─────── 30-95 parts Surfactant ─────── 5 to 15 parts

[Flowable agent] Compound of the present invention ─────── 5 to 70 parts Liquid carrier ─────── 15 to 65 parts Surfactant ─────── 5 to 12 parts Others ─ ────── 5-30 parts Others include, for example, antifreezing agents, thickeners and the like.

[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 ─────── 90-99.9 parts Other ─────── 1-5 parts

[Formulation Example 1] Wettable powder Inventive Compound C-7 ───────── 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] Milk Compound C-7 of the present invention ──────── 3 parts xylene ──────── 76 parts Isophorone ───────── 15 parts Solpol 3005X ──────── 6 parts (mixture of nonionic surfactant and anionic surfactant: trade name of Toho Kagaku Kogyo Co., Ltd.) The above components are uniformly mixed to form an emulsion.

[Formulation Example 3] Flowable agent Inventive Compound C-7 ──────── 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 C-7 ───────── 75 parts Isoban No. 1 ───────── 10 parts (anionic Surfactant: 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: Shionogi Seiyaku Co., Ltd. trade name) The above is uniformly mixed and pulverized to obtain a dry flowable agent.

[Formulation Example 5] Granules Compound of the present invention C-7 ─────── 0.1 parts Bentonite ─────── 55.0 parts Talc ──────── 44.9 parts The above are uniformly mixed. After crushing, a small amount of water is added, and the mixture is kneaded with stirring, granulated by an extrusion granulator, and dried to give granules.

[Formulation Example 6] Wettable powder Inventive compound C-11 ───────── 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 7] Milk compound C-11 of the present invention ──────── 3 parts xylene ──────── 76 parts Isophorone ───────── 15 parts Solpol 3005X ──────── 6 parts (mixture of nonionic surfactant and anionic surfactant: trade name of Toho Kagaku Kogyo Co., Ltd.) The above components are uniformly mixed to form an emulsion.

[Formulation Example 8] Flowable agent Inventive compound C-11 ───────── 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.

[Compounding Example 9] Granular wettable powder (dry flowable agent) Compound C-11 of the present invention ────────────────────────────────────────────────────── Surfactant: 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: Shionogi Seiyaku Co., Ltd. trade name) The above is uniformly mixed and pulverized to obtain a dry flowable agent.

[Formulation Example 10] Granules Compound of the present invention C-11 ─────── 0.1 parts Bentonite ─────── 55.0 parts Talc ──────── 44.9 parts The above are uniformly mixed. After crushing, a small amount of water is added, and the mixture is kneaded with stirring, granulated by an extrusion granulator, and dried to give granules.

[Formulation Example 11] Wettable powder Compound C of the present invention C-27 ───────── 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 12] Emulsion Compound C-27 of the present invention ──────── 3 parts xylene ──────── 76 parts Isophorone ───────── 15 parts Sorpol 3005X ──────── 6 parts (mixture of nonionic surfactant and anionic surfactant: trade name of Toho Kagaku Kogyo Co., Ltd.) The above components are uniformly mixed to form an emulsion.

[Formulation Example 13] Flowable agent Inventive compound C-27 ───────── 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 14] Granular wettable powder (dry flowable agent) Compound C of the present invention C-27 ──────── 75 parts Isoban No. 1 ───────── 10 parts (anionic Surfactant: 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: Shionogi Seiyaku Co., Ltd. trade name) The above is uniformly mixed and pulverized to obtain a dry flowable agent.

[Formulation Example 15] Granules Compound of the present invention C-27 ─────── 0.1 parts Bentonite ─────── 55.0 parts Talc ──────── 44.9 parts The above are uniformly mixed. After crushing, 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 wettable powder, emulsion, flowable powder, and granular wettable powder are diluted 50 to 1000 times with water and sprayed so that the active ingredient is 0.0001 to 10 kg per hectare (ha). . 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 [0127] A sterilized diluvial soil was put in a plastic box having a length of 15 cm, a width of 22 cm, and a depth of 6 cm. ,
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 4.

Judgment Criteria 5-Hericidal rate 90% or more (almost complete death) 4-Hericidal 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) × 100 The symbols in each table have the following meanings. N (Novier), M (Mexico), K (Cyperus),
H (Penunculus japonicus), D (Ballaceae), I (Purple), R (Rice), T (Maize), W (Wheat), S (Soybean), C (Cotton)

[0130]

[Table 9]

[0131]

[Table 10]

   ─────────────────────────────────────────────────── ─── Continued front page    (72) Inventor Hiroshi Kita             1 Nissan Chemical, 722, Tsuboi-cho, Funabashi, Chiba             Central Research Institute (72) Inventor Yasuo Kawamura             1 Nissan Chemical, 722, Tsuboi-cho, Funabashi, Chiba             Central Research Institute (72) Inventor Koichi Suzuki             1470 Shiraoka, Shirooka-cho, Minami-Saitama-gun, Saitama             Gaku Kogyo Co., Ltd. Biological Science Laboratory (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 Toshiharu Endo             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 ⁴ represents a hydrogen atom or a halogen atom,
R ⁵ represents a halogen atom, D ²⁶ represents an alkyl group having 1 to 4 carbon atoms, or a haloalkyl group having 1 to 3 carbon atoms. ] The uracil derivative represented by these. 2. Formula (I): [In the formula, R ⁴ represents a hydrogen atom, a fluorine atom or a chlorine atom, and R ⁵ represents a chlorine atom. ] The uracil derivative of Claim 1 represented by these. 3. Formula (I): [In the formula, R ⁴ represents a hydrogen atom, a fluorine atom or a chlorine atom, and R ⁵ represents a bromine atom. ] The uracil derivative of Claim 1 represented by these. 4. A herbicide containing the uracil derivative according to claim 1.