JPH0692943A - Dihydropyrimidinedione derivative and herbicide - Google Patents

Abstract

PURPOSE:To provide the novel compound exhibiting high effects at low doses against various weeds by the treatment of soil and by the treatment of stems and soils. CONSTITUTION:The compound of formula I (R<1> is methyl, amino; R<4> is H, halogen; R<5> is halogen; D<26> is 1-4C alkyl, 1-3C haloalkyl), e.g. 3-(4-chloro-5- ethylsulfonylamino-2-fluorophenyl)-1-methyl-6-trifluoromethyl-5,6-dihy dro-2,4-(1H,3 H)-pyrimidinedione. The compound of formula I is obtained by reacting a beta- aminoacrylate ester of formula II with an N-phenylcarbamate of formula III (G<2> is 1-4C alkyl, phenyl), reacting the produced uracil derivative of formula IV with a methylating agent or an aminating agent and subsequently reducing the uracil ring. The compound of formula I has strong herbicidal forces against Graminales weeds, Cyperales weeds, paddy field weeds, broad-leaved weeds, etc., but does not cause chemical damages to crops such as wheat, corn, barley, soybean, rice, etc.

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to a novel dihydropyrimidinedione 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. . 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, 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, etc. depending on the method of applying 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) , It is possible to sow and transplant the next crop 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 phytotoxicity that poses a problem to crops (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 pyrimidinedione derivative exhibits herbicidal activity, which is described in, for example, European Patent Application Publication No. 408382. Further, it is known that a specific compound of the dihydropyrimidinedione derivative exhibits herbicidal activity, which is described in, for example, US Pat. No. 4,927,451.

[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 ¹ represents a methyl group or an amino group, R ⁴ represents a hydrogen atom or a halogen atom, and 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 dihydropyrimidinedione derivative represented by the formula (hereinafter referred to as the compound of the present invention) was found.

Compared with conventional herbicides, the compound of the present invention can be applied to various kinds of weeds including perennial weeds by either soil treatment or foliage treatment, and is quick-acting despite spraying with a low dose. It has a great feature that it has a high effect and has an appropriate residual effect. The compound of the present invention is a field, paddy field, as a herbicide for non-cultivated land, soil treatment, in any treatment method of foliage treatment, dogwood,
Datura, Bombyx striata, American stag deer, Malva morning glory, Inuyuyu, Aubiyu, Onami fir, Ragweed, Sunflower, Toothbrush, Prickly thistle, Naboroshi, Himejon, Dogwood, Pleurotus cornucopia, Pleurotus cornucopia, Bombyx vulgaris, Pleurotus cornucopia Broad-leaved weeds such as chickweed, Stellaria japonica, communis, serrata, Astragalus lanceolata, C. perennial, C. perennial, Yaemgra, Akane, Violet, Astragalus vulgare, Ebisugusa, Kosendangusa, wild sorghum, millet grass, johnson grass
Weeds such as barnyardgrass, sandgrass, oats, cerebrograss, green foxtail, periwinkle, etc. It has high herbicidal activity with low dosage in paddy field weeds.
Also important crops are wheat, corn, barley, soybeans,
Can be safely used for rice, etc.

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 Scheme 1 (R ¹ in Scheme ¹ ,
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, and G ² represents an alkyl group having 1 to 4 carbon atoms or a phenyl group. ).

[0011]

[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. Or continuously without isolation, as a second step, the 1-position of the uracil ring is methylated or aminated to synthesize a uracil derivative (I ″), and as a third step, the uracil ring is reduced to give a dihydropyrimidinedione derivative. It represents a method for producing (I).

First Step Reaction Usually, (VII) is 0.5 to 1.5 equivalents, preferably 0.8 with respect to (V).
Use ~ 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, halogenated carbonization such as chloroform and methylene chloride. Hydrogen, 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 and sulfolane, alcohols such as methanol, ethanol, propanol and butanol, water and these Examples thereof include a mixture, preferably the above-mentioned aliphatic hydrocarbons, aromatic 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, preferably inorganic bases such as potassium carbonate and sodium hydride, metal alcoholates such as sodium methoxide. Kind of things.

The reaction temperature is usually 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 stage In the case of methylation, 0.5 to 10 equivalents, preferably 0.8 to 5.0 equivalents of a methylating agent is used with respect to (I ′). Examples of the methylating agent include methyl halides such as dimethyl sulfate, methyl chloride, methyl bromide and methyl iodide. In the case of amination, 0.5 to 5.0 equivalents, preferably 0.8 to 2.0 equivalents of aminating agent is used with respect to (I '). 2,4 as aminating agent
-Phenoxyamines such as dinitrophenoxyamine, O
-Mesitylenesulfonylhydroxyamine, sulfonylhydroxyamines such as Op-toluenesulfonylhydroxyamine, chloramine and cyclohexanespiro 3 '
-Examples include oxaziridine.

For both the methylation and amination reactions, it is usually preferable to use a solvent. Hexane as solvent,
Aliphatic hydrocarbons such as heptane, ligroin and petroleum ether, aromatic hydrocarbons such as benzene, toluene, xylene and chlorobenzene, halogenated hydrocarbons such as chloroform and methylene chloride, ethers such as diethyl ether, dioxane and tetrahydrofuran. , Ketones such as acetone and methyl ethyl ketone, nitriles such as acetonitrile and isobutyronitrile, tertiary amines such as pyridine and N, N-diethylaniline, N, N-dimethylacetamide, N, N-dimethylformamide Acid amides such as N-methylpyrrolidone, sulfur-containing compounds such as dimethylsulfoxide and sulfolane, water and mixtures thereof, preferably aliphatic hydrocarbons, aromatic hydrocarbons, ethers and ketones. , Nitriles, acid amides, sulfur-containing compounds and And mixtures of these.

Usually, 0.5 to 10 equivalents, preferably 0.8 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,
Nitrogen-containing organic bases such as 4-diazabicyclo [2.2.2] octane, and inorganic bases such as sodium hydride, potassium hydride, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, and the like, and preferably sodium hydride Inorganic bases such as potassium carbonate.

The reaction temperature is usually -30 to 150 ° C, preferably
It is carried out 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. As the reducing method of the third step (I ″), a method of using a metal-hydrogen complex compound such as lithium aluminum hydride or sodium borohydride, a metal-hydrogen compound such as diisobutylaluminum hydride, or the like, There is a method using a catalytic hydrogenation reaction, and a method using soil bacteria.

When a reducing agent is used, the reducing agent is used in an amount of 0.5 to 10 equivalents, preferably 0.8 to 3.0 equivalents, relative to (I ''). The reaction usually requires a solvent, hexane as a solvent,
Aliphatic hydrocarbons such as heptane, ligroin and petroleum ether, aromatic hydrocarbons such as benzene, toluene, xylene and chlorobenzene, halogenated hydrocarbons such as chloroform and methylene chloride, ethers such as diethyl ether, dioxane and tetrahydrofuran. , 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, alcohols such as methanol, ethanol, propanol and butanol, and mixtures thereof, and preferably the above aliphatic hydrocarbons, aromatic hydrocarbons, ethers and mixtures thereof. Can be given.

The reaction temperature is usually -30 to 200 ° C., preferably
It is carried out at 0 ° C. to the reflux temperature of the reaction mixture. The reaction time is usually 10 minutes to 96 hours, preferably 20 minutes to 48 hours.
The synthesis examples of the compound of the present invention and the intermediate will be specifically described below as Examples, but the present invention is not limited thereto.

[0022]

【Example】

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

[0023]

[Chemical 6]

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

[0027]

[Chemical 7]

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 3 3- (4-chloro-5-ethylsulfonylamino-2-
Synthesis of fluorophenyl) -1-methyl-6-trifluoromethyl-5,6-dihydro-2,4 (1H, 3H) -pyrimidinedione (invention compound No. 1)

[0031]

[Chemical 8]

A solution of 3- (4-chloro-5-ethylsulfonylamino-2-fluorophenyl) -1-methyl-6-trifluoromethyl-2,4 (1H, 3H) -pyrimidinedione (2 g) and tetrahydrofuran (20 ml) was added. Sodium borohydride (0.176 g) was added at 0 ° C., and the mixture was slowly returned to room temperature and stirred for 4 hours. Pour the reaction mixture into 400 ml of water,
The mixture was acidified with concentrated hydrochloric acid and extracted with ethyl acetate. After washing with water and saturated saline in this order, drying over anhydrous sodium sulfate,
The solvent was distilled off under reduced pressure to obtain a crude product. This was recrystallized from chloroform-ethyl acetate to obtain 0.97 g of the desired compound (yield 48.5%) as white crystals. Melting point 181 to 184 ° C

¹ H-NMR (CDCl ₃ ) δ (ppm): 1.35 (3H, t, J = 7H
z), 2.95-3.48 (4H, m), 3.30 (3H, s), 3.95-4.36 (1H, m), 6.
98 (1H, br s), 7.36 (1H, d, J = 9Hz), 7.70 (1H, d, J = 7Hz) The compound of the present invention synthesized according to the scheme or the example was synthesized in the example. The compounds, including compounds, are shown in Table 1, but the invention is not limited thereto.

[0034]

[Table 1]

[0035]

[Table 2]

[0036]

[Table 3]

When the compound of the present invention is applied as a herbicide, generally, a suitable carrier, for example, a solid carrier such as clay, talc, bentonite, diatomaceous earth, and white carbon, or water, alcohols (isopropanol, butanol, benzyl alcohol, fluroalcohol) is 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 with other types of herbicides, various insecticides, fungicides, plant growth regulators, synergists and the like at the time of 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 herbicide 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) Compounds described in the 1990 edition.

The application dose of the compound of the present invention varies depending on the application scene, application time, application method, cultivated crop, etc., but is 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 ─────── 5-80 parts Solid carrier ─────── 10-85 parts Surfactant ─────── 1-10 parts Others ─────── 1-5 parts Other examples 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 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 to 90 parts Solid carrier ─────── 10 to 60 parts Surfactant ────── ─ 1-20 copies

[Granule] Compound of the present invention ─────── 0.1 to 10 parts Solid carrier ─────── 90 to 99.9 parts Others ─────── 1 to 5 parts

[Formulation Example 1] Wettable powder Compound of the present invention No. 1 ───────── 50 parts Dichlorite PFP ──────── 43 parts (Kaolin-based clay: Siglite Industrial Co., Ltd. ) Product name) Solpol 5050 ───────── 2 parts (Anionic surfactant: Toho Chemical Industry Co., Ltd. product name) Lunox 1000 C ───────── 3 parts (Anionic surfactant Agent: Toho Chemical Industry Co., Ltd. product name) Carplex # 80 (anti-caking agent) ─-2 parts (white carbon: Shionogi Pharmaceutical Co., Ltd. product name) To do.

[Formulation Example 2] Emulsion Compound of the present invention No. 1 ───────── 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 ingredients are uniformly mixed to form an emulsion.

[Formulation Example 3] Flowable agent Compound No. 1 of the present invention ───────── 35 parts Agrisol S-711 ──────── 8 parts (Nonionic surfactant: Kao ( Trade name) Lunox 1000 C ──────── 0.5 part (Anionic surfactant: Toho Chemical Industry Co., Ltd. trade name) 1% Rhodopol water ───────── 20 parts (increase) Sticky agent: Trade name of Lorne Poulin Co., Ltd. Ethylene glycol (antifreeze) ── 8 parts Water ──────── 28.5 parts Mix the above uniformly to make a flowable agent.

[Formulation Example 4] Granular wettable powder (dry flowable agent) Compound of the present invention No. 1 ───────── 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: trade name of Shionogi Pharmaceutical Co., Ltd.) The above is uniformly mixed and pulverized to obtain a dry flowable agent.

[Formulation Example 5] Granules Compound of the present invention No. 1 ─────── 0.1 parts Bentonite ─────── 55.0 parts Talc ──────── 44.9 parts The above components are mixed uniformly. 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 A sterilized diluvial soil was put in a plastic box having a length of 30 cm, a width of 30 cm, and a depth of 7 cm.
Seeds of morning glory, stag deer, ragweed, white azalea, and corn were sown in spots, respectively, and covered with soil for about 1.5 cm, and then uniformly sprayed on the soil surface with a small spray so that the amount of active ingredient was a predetermined ratio. The chemical solution for spraying is
A wettable powder, which was appropriately adjusted according to the above-mentioned formulation example, 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 2.

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

[0054]

[Table 4]

Front page continued (72) Inventor Hiroshi Kita, 722, Tsuboi-cho, Funabashi-shi, Chiba, Central Research Laboratory, Nissan Chemical Industries, Ltd. (72) Inventor, Naoshi Nakata 722, Tsuboi-cho, Funabashi, Chiba, Nissan Chemical Co., Ltd. Company Central Research Institute (72) Inventor Namaki Tsutomu 1470 Shiraoka, Shiraoka-cho, Minamisaitama-gun, Saitama Nissan Chemical Industry Co., Ltd.Biological Sciences Research Institute (72) Inventor Shigeomi Watanabe 1470 Shiraoka, Shiraoka-cho, Minami-Saitama-gun, Saitama 1470 Nissan Kagaku Industrial Co., Ltd.Institute for Biological Sciences (72) Inventor Kimihiro Ishikawa 1470 Shiraoka, Shiraoka-cho, Minamisaitama-gun, Saitama Nissan Chemical Industry Co., Ltd.Institute for Biological Sciences (72) Yoichi Ito 1470 Shiraoka, Shiraoka-cho, Minami-Saitama-gun, Saitama 1470 Nissan (72) Inventor Hiroaki Hirata 1470 Shiraoka, Shiraoka-cho, Minamisaitama-gun, Saitama Nissan Chemical Industry Co., Ltd.

Claims (4)

[Claims] 1. Formula (I): [In the formula, R ¹ represents a methyl group or an amino group, 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 the number of carbon atoms. 1 to 3 represents a haloalkyl group. ] The dihydropyrimidine dione derivative represented by these. 2. Formula (I): [In the formula, R ¹ represents a methyl group, R ⁴ represents a hydrogen atom, a fluorine atom or a chlorine atom, and R ⁵ represents a chlorine atom. ]
The dihydropyrimidinedione derivative according to claim 1, represented by: 3. Formula (I): [In the formula, R ¹ represents a methyl group, R ⁴ represents a hydrogen atom, a fluorine atom or a chlorine atom, and R ⁵ represents a bromine atom. ]
The dihydropyrimidinedione derivative according to claim 1, represented by: 4. A herbicide containing the dihydropyrimidinedione derivative according to claim 1.