JPH05202031A - N-aminopyrimidindione derivative and herbicide - Google Patents

Abstract

PURPOSE:To obtain the subject new N-aminopyrimidindione derivative, capable of exhibiting selectivity for important crops, having excellent herbicidal effects on various weeds in a small amount of chemical and useful as a herbicide having soil and foliar treatment effects in combination. CONSTITUTION:The objective compound of formula I [R<1> is 1-4C haloalkyl; R2 is H, halogen, 1-4C alkyl or NO2; R<3> is NH2; X is O; A is substitutable phenyl (with the proviso that the phenyl is unsubstituted when A is bound to Y at the m-position) or substitutable 5-to 6-membered heterocyclic ring containing at least one or more of N, O and S as a ring-forming atom; Y is O; L is 1-3C alkylene substitutable with one or more methyls; m is 0 or 1; Q is respectively substitutable phenyl ring, naphthalene ring or 5-to 6-membered heterocyclic ring], e.g. 1-amino-3-(6-phenoxypyridin-3-yl)-6-trifluoromethyl-2,4 (1H, 3H)-pyrimidindione. This compound is obtained by reaction according to the reactional formulas.

Description

Detailed Description of the Invention

[0001]

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

[0002]

2. Description of the Related Art In recent years, it is clear that the productivity of important crops affects the food economy of each country as the population of the world increases. With these changes, it is inevitable that the traditional agricultural form will change toward the 21st century. Actually, it is more and more necessary for farmers to develop a herbicide capable of economically and efficiently killing or controlling weeds that interfere with crop cultivation.

As such a herbicide, 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 a moderate residual effect (remaining soil residue in recent years). It has been a problem that long-term drugs will damage subsequent crops, and it is important to show a moderate residual effect after spraying.) Those that kill weeds immediately after spraying (chemical treatment) After that, 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 agricultural workers to reduce the number of complicated weed control work as much as possible), Weed control is wide-ranging (for broad-leaved weeds, gramineous weeds, perennial weeds, and other weed species with different properties, it is desirable that a single agent be able to control them). Combines soil treatment and foliage treatment effects By having it, a stronger herbicidal effect can be obtained.), One that does not show harmful chemical damage to crops (that can selectively kill only weeds in arable land where crops and weeds are mixed) Is preferable.) Is preferable. However, existing herbicides do not meet all of these requirements.

Known references relating to uracil compounds include US Pat. Nos. 3,580,913 and 3,86.
There are 9,457 and 3,981,715. These documents describe the herbicidal action of pyrimidinedione derivatives in which the 3-position of the pyrimidine ring is substituted with alkyl, phenyl or the like. However, the pyrimidinedione derivative which is the compound of the present invention is one in which an aryloxy group or an arylalkyloxy group is substituted on a phenyl ring or a heterocycle bonded to the 3-position of the pyrimidine ring, and the nitrogen atom at the 1-position of the pyrimidine ring is further substituted. It is a substituted amino group, which is different from these known documents.

[0005]

In view of such a situation, the present inventors show selectivity for important crops and have excellent herbicidal effect on 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)

[0006]

[Chemical 5]

[In the formula, R ¹ represents a C _{1 to} C ₄ haloalkyl group, R ² represents a hydrogen atom, a halogen atom, a C _{1 to} C ₄ alkyl group or a nitro group, and R ³ represents an amino group, X represents an oxygen atom, A is a phenyl ring which may be substituted (however, when A is bonded to Y at the meta position, A represents an unsubstituted phenyl ring), or a nitrogen atom or oxygen as a ring-forming atom. An optionally substituted 5-membered or 6-membered heterocycle containing at least one atom or sulfur atom, Y represents an oxygen atom, and L is substituted with one or more methyl groups. Is a C _{1 to} C ₃ alkylene chain, m is 0 or 1, and Q is an optionally substituted phenyl ring, an optionally substituted naphthalene ring, or a nitrogen atom or oxygen as a ring-forming atom. At least of atoms and sulfur atoms Optionally substituted 5-membered heterocyclic ring containing more pieces, shows a 6-membered heterocyclic or condensed heterocyclic ring. ] The N-amino pyrimidine dione derivative represented by these (it calls the compound of this invention hereafter) was discovered.

Examples of A include a phenyl ring and a heterocycle represented by the following formula.

[0009]

[Chemical 6]

(In the formula, Z is a halogen atom, a C ₁ -C ₄ alkyl group, a C ₁ -C ₄ alkoxy group, a C ₁ -C ₄ haloalkyl group, a C ₁ -C ₄ haloalkoxy group, a carboxy group or C ₁ To C ₄ alkoxycarbonyl group, and n represents 0, 1 or 2. As Q, for example, a phenyl ring represented by the following formula,
Examples thereof include naphthalene ring and heterocyclic ring.

[0011]

[Chemical 7]

(Where R is^Four, R^FiveAre each independently hydrogen
Atom, halogen atom, C₁~ C_FourAlkyl group, C₁~ C
_FourHaloalkyl group, C₁~ C_FourAlkoxy group, C₁~ C
_FourRepresents a haloalkoxy group, a nitro group or a cyano group,
R⁶Is a hydrogen atom or C₁~ C _FourIndicates an alkyl group. ) The compound of the present invention is used as a herbicide for upland fields, paddy fields and non-cultivated land, in soil.
It can be used in both loom treatment and foliage treatment.
Wear.

The target weeds of the compound of the present invention are, as the target weeds, Amaranthus perforatum, Datura perforatum, Prickly pear, American stag deer, Malaba morning glory, Amaranthus perforatum, Aubiyu, Onami fir,
Ragweed, sunflower, boxwood, thorns thistle, syringa, himejon, puffin, haragashi, nazuna, scutellaria, buckwheat, purslane, white cypress, koakaza, houkigi, boxweed, stinkweed,
Broad-leaved weeds such as communis, moss, Astragalus chinensis, Astragalus membranaceus, Cinnabarium, Yaemgra, Akane, Violet, Weed, Wild sorghum, Stinkweed, Steller's grasshopper, Steller's grasshopper, Steller's grasshopper, Stinkweed Weeds of grasses, Cyperaceae weeds such as scutellaria, Heraomodaka, Omodaka,
Urikawa, Tamagayatsuri, Mizugaya-tsuri, Firefly, Kurogwai, Azena, Kokonagi, Hirumushiro, Kishigusa,
Examples include Tainubie.

The compounds of the present invention include compounds that can be safely used in important crops such as wheat, corn, barley, soybean, rice, cotton, beet, sorghum and the like. The compounds of the present invention are also useful as defoliants. Examples of the synthetic method of the compound of the present invention include, for example, Comprehensive Heterocyclic Chemistry, Vol. 3, p. 57, 19
1984 (AR Katritzky, et al., Comprehensive Hete
The uracil bone nucleus can be synthesized by referring to the synthetic method described in rocyclic Chemistry, 3 , 57 (1984)), and the N-amination of the uracil ring can be performed by Journal of the Chemicals. Society Perkin
Transaction I, Volume 6, 545, 1973 (Charles W. Rees, et al., J. Chem. Soc. Perkin Tr
ans. I, 6 , 545 (1937)) and the like. Furthermore, 3-amino-4, which is one of the starting materials,
4,4-Trifluorocrotonates are reported in Journal of Heterocyclic Chemistry, 9th
Volume, 513, 1972 (AW Lutz, et al., J. H.
It can be synthesized with reference to eterocycl. Chem., 9 (3), 513 (1972)) and the like.

Schemes (1) to (1) including the above method
The compound of the present invention can be obtained by the synthetic route shown in (3). Scheme (1)

[0016]

[Chemical 8]

Scheme (2)

[0018]

[Chemical 9]

Scheme (3)

[0020]

[Chemical 10]

R in scheme (1)¹, R², R³, A,
Y, L, m and Q have the same meanings as described above. G
¹Is, for example, lower alkyl group, benzyl group, phenyl
Group, CH ₂CO₂H is represented, and acid is, for example,
Represents paratoluene sulfonic acid, concentrated sulfuric acid, etc.
Is, for example, sodium hydride, sodium
And potassium carbonate, and the aminating agent is, for example,
2,4-dinitrophenoxyamine, O-mesitylene
Rufonylhydroxylamine, Op-toluenesulfo
Nylhydroxylamine, chloramine, cyclohexane
Represents spiro 3'-oxaziridine and the like.

R ¹ , R ² , R ³ , A in the scheme (2),
X, Y, L, m and Q have the same meanings as described above. G
¹ and G ² each independently represent, for example, a lower alkyl group, a benzyl group, a phenyl group, CH ₂ CO ₂ H or the like, and base represents, for example, sodium hydride, sodium methoxide, potassium carbonate or the like, The aminating agent is, for example, 2,4-dinitrophenoxyamine, O-
Mesitylenesulfonylhydroxylamine, Op-toluenesulfonylhydroxylamine, chloramine, cyclohexanespiro3'-oxaziridine and the like are represented.

R ¹ , R ² , R ³ , A in the scheme (3),
Y, L, m and Q have the same meanings as described above. Examples of the halogenating agent include fluorine, chlorine, bromine, iodine, sulfuryl chloride, etc., and examples of the nitrating agent include nitric acid, copper nitrate, isoamyl nitrate, etc., and the aminating agent includes, for example, 2, 4-dinitrophenoxyamine, O-mesitylenesulfonylhydroxylamine, O
-P-toluenesulfonylhydroxylamine, chloramine, cyclohexanespiro3'-oxaziridine and the like are represented.

When it becomes necessary to purify the compound of the present invention, it can be separated and purified by any purification method such as recrystallization and column chromatography. Among the compounds included in the present invention, the compounds having an asymmetric carbon include the optically active compounds (+) form and (−) form. The synthesis examples of the compound of the present invention will be specifically described below as examples, but the present invention is not limited thereto.

[0025]

【Example】

Example 1 1-Amino-3- (6-phenoxypyridin-3-yl) -6-trifluoromethyl-2,4 (1
Synthesis of (H, 3H) -pyrimidinedione. (Inventive Compound No. 1)

[0026]

[Chemical 11]

(1) To a mixture of 4.4 g of ethyl 3-amino-4,4,4-trifluorocrotonate and 20 ml of N, N-dimethylformamide at 0 to 5 ° C, 960 mg of sodium hydride (oil, purity: ca. 60%) was gradually added.
After the addition, the mixture was stirred at room temperature for 1 hour, 3- (ethoxycarbonylamino) -6-phenoxypyridine (6.2 g) was added, and the mixture was stirred at 110 to 120 ° C for 5 hours. After the reaction,
After distilling off N, N-dimethylformamide under reduced pressure,
200 ml of water was added and washed with ether. The pH of the water tank was adjusted to about pH 4 with concentrated hydrochloric acid, and the precipitated crystals were collected by filtration and dried,
4.5 g of 3- (6-phenoxypyridin-3-yl) -6-trifluoromethyl-2,4 (1H, 3H) -pyrimidinedione was obtained as white crystals. Melting point 227-22
8 ° C

(2) 3- (6-phenoxypyridin-3-yl) -6-trifluoromethyl-obtained above
To a mixture of 880 mg of 2,4 (1H, 3H) -pyrimidinedione, 500 mg of anhydrous potassium carbonate and 10 ml of N, N-dimethylformamide was added 500 mg of 2,4-dinitrophenoxyamine, and the mixture was stirred at room temperature for 2 days. The reaction solution was poured into water and extracted with ethyl acetate. The organic layer was washed with water, then with 5% aqueous sodium hydroxide solution and saturated saline,
It was dried over anhydrous sodium sulfate. After the solvent was distilled off under reduced pressure, the residue was washed with a small amount of ether to obtain 690 mg of the target compound (Compound No. 1 of the invention) as pale yellow crystals. Melting point 195 to 196 ° C. ¹ H-NMR (CDCl ₃ ), δ (ppm): 4.61
(2H, s), 6.25 (1H, s), 6.90-8.
06 (8H, m)

Table 1 shows the numbers and structures of the compounds synthesized according to the examples or schemes, and Table 2 shows the physical properties of these compounds.

[0030]

[Chemical 12]

[0031]

Next, examples of the compounds included in the present invention are shown in Tables 3 to 5, including the compounds 1 to 3 above, but the present invention is not limited thereto. (However, in the table, Me represents a methyl group, Et an ethyl group, Pr a propyl group, Bu a butyl group, t a tertiary, s a secondary and i an iso.) Among the included compounds, the compound having an asymmetric carbon atom includes the (+) form and the (−) form of the optically active compound.

Table 3

[0034]

[Chemical 13]

[0035]

[0036]

[0037]

[0038]

[0039]

[0040]

[0041]

[0042]

[0043]

[0044]

[0045]

[0046]

[0047]

[0048]

[0049]

Table 4

[0051]

[Chemical 14]

[0052]

[0053]

[0054]

[0055]

Table 5

[0057]

[Chemical 15]

[0058]

[0059]

[0060]

Q1 to Q42 in Tables 3 to 5 above
Is a group represented by the following structural formula.

[0062]

[Chemical 16]

[0063]

[Chemical 17]

[0064]

[Chemical 18]

The application dose of the compound of the present invention varies depending on the application scene, application time, application method, cultivated crop, etc., but generally 0.01 to 10 kg per hectare (ha) as an active ingredient amount.
It is suitable that the amount is about 0.05 to 5 kg. Also,
If necessary, the compound of the present invention may be mixed with other 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 another herbicide, it is expected that the cost can be reduced by reducing the amount of the applied agent, the herbicidal spectrum can be expanded by the synergistic action of the mixed agents, and a higher herbicidal effect can be expected. 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, Farm Chemicals Handbook 1990.
There are compounds listed in the annual edition.

When the compound of the present invention is applied 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, 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.

Next, specific examples of formulation of the preparation when the compound of the present invention is used will be 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 [Fluble] Agent] Compound of the present invention ─────── 5-70 parts Liquid carrier ─────── 15-65 parts Surfactant ──────── 5-12 parts Others ────── -5 to 30 parts Other examples include antifreezing agents and thickeners.

[Granular wettable powder (dry flowable agent)] Compound of the present invention ─────── 20 to 90 parts Solid carrier ──────── 10 to 60 parts Surfactant ────── ─ 1 to 20 parts [Granule] Compound of the present invention ─────── 0.01 to 10 parts Solid carrier ─────── 90 to 99.99 parts Others ──────── 0 to 5 parts [Compound] Example 1] Wettable powder Compound of the present invention No. 1 ───────── 50 parts Dichlorite PFP ──────── 43 parts (Kaolin-based clay: trade name of Sikhlite Industrial Co., Ltd.) Sorpol 5050 ──────── 2 parts (Anionic surfactant: trade name of Toho Chemical Industry Co., Ltd.) Lunox 1000 C ──────── 3 parts (Anionic surfactant: Toho Chemical Industry) Product name: Carplex # 80 (anti-caking agent)-2 parts (White carbon: manufactured by Shionogi Ltd. trade name) were uniformly mixed and pulverized over a wettable powder.

[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 components are uniformly mixed to form an emulsion.

[Formulation Example 3] Flowable agent Compound of the present invention No. 1 ──────── 35 parts Aglisol 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. 2 ───────── 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] Granule Compound of the present invention No. 3 ─────── 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, kneaded, 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 0.01 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 15 cm, a width of 22 cm, and a depth of 6 cm, and Novier, Mehsisgrass, Cyperus serrata, Podocarpus serrata, Pleurotus cornucopiae, Pinegrass, Rice,
Mixed seed 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 and the like was diluted with water and used. Three weeks after spraying the chemical solution, the herbicidal effect on various weeds and crops was visually examined according to the following criteria. The results are shown in Table 6.

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 ineffective)

[Test Example 2] Herbicidal effect test by foliar treatment: sterilized diluvial soil was placed in a plastic box having a length of 15 cm, a width of 22 cm, and a depth of 6 cm, and Novier, Mehsisgrass, Cyperus serrata, Podocarpus serrata, Pleurotus cornucopiae, Pinegrass, rice,
Seeds of corn, wheat, soybean, cotton, and beet were sowed in spots and covered with soil for about 1 cm. When various plants reached the 2-3 leaf stage, the active ingredients were sprayed uniformly on the foliage so that the amount of the active ingredient became 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 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 7.

The symbols in each table have the following meanings. N (Novier), M (Mexico), K (Cyperus),
H (Penguinosa), D (Balleyes), I (Purple), R (Rice), T (Maize), W (Wheat), S (Soybean), C (Cotton), B (Beet)

[0081]

[0082]

─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. ⁵ Identification number Office reference number FI technical display location A01N 43/66 8930-4H 43/76 8930-4H 101 8930-4H 43/78 C 8930-4H 101 8930-4H 43/80 101 8930-4H 102 8930-4H 43/82 104 8930-4H C07D 239/54 401/12 8829-4C 401/14 8829-4C 403/12 8829-4C 405/12 8829-4C 409 / 12 8829-4C 413/12 8829-4C 417/12 9051-4C (72) Inventor Kaoru Ito 1 722, Tsuboi-cho, Funabashi-shi, Chiba Central Research Laboratory, Nissan Chemical Industries, Ltd. (72) Inventor Hiroshi Kita Chiba 1 722, Tsuboi-cho, Funabashi-shi, Fukushima, Central Research Laboratory, Nissan Chemical Industries, Ltd. (72) Tsutomu Namaki, 1470, Shiraoka, Shiraoka-cho, Minamisaitama-gun, Saitama Nissan Chemical Industry Co., Ltd., Institute for Biological Sciences (72) Inventor, Watanabe Shigeomi South of Saitama Prefecture 1470 Shiraoka, Shiraoka-cho, Saitama-gun, Nissan Kagaku Kogyo Co., Ltd., Institute of Biological Sciences (72) Inventor, Kimihiro Ishikawa 1470, Shiraoka, Shiraoka-cho, Minami Saitama-gun, Saitama-gun

Claims (3)

[Claims] 1. Formula (1): [In the formula, R ¹ represents a C _{1 to} C ₄ haloalkyl group, and R ²
Represents a hydrogen atom, a halogen atom, a C ₁ -C ₄ alkyl group or a nitro group, R ³ represents an amino group, X represents an oxygen atom, and A represents a phenyl ring which may be substituted (however, A
When is bonded to Y at the meta position, A represents an unsubstituted phenyl ring. ), Or an optionally substituted 5-membered heterocycle or 6-membered heterocycle containing at least one or more of a nitrogen atom, an oxygen atom and a sulfur atom as a ring-forming atom,
Y represents an oxygen atom, L represents a C _{1 to} C ₃ alkylene chain which may be substituted with one or more methyl groups, m represents 0 or 1, and Q represents phenyl which may be substituted. A ring, an optionally substituted naphthalene ring, or an optionally substituted 5-membered heterocycle, 6-membered heterocycle or fused heterocycle containing at least one or more of a nitrogen atom, an oxygen atom and a sulfur atom as a ring-forming atom. Indicates a ring. ] The N-amino pyrimidine dione derivative represented by these. 2. Formula (1):[In the formula, R¹Is C₁~ C_FourRepresents a haloalkyl group, R²
Is hydrogen atom, halogen atom, C₁~ C_FourAlkyl group
Represents a nitro group, R³Is an amino group, X is an oxygen source
Child, Y is an oxygen atom, L is one or more methyl
C optionally substituted with a group₁~ C₃The alkylene chain of
, M is 0 or 1, and A is the following formula:(In the formula, Z is a halogen atom, C₁~ C_FourAlkyl group, C
₁~ C_FourAlkoxy group, C₁~ C_FourHaloalkyl group, C
₁~ C_FourHaloalkoxy group, carboxy group or C₁~
C_FourRepresents an alkoxycarbonyl group, n is 0, 1 or
2 is shown. ), And Q is the following formula:(In the formula, R^Four, R^FiveAre independently hydrogen atom and halogen
Atom, C₁~ C_FourAlkyl group, C₁~ C_FourHalo Archi
Lu group, C₁~ C_FourAlkoxy group, C₁~ C_FourHalo arco
R represents an oxy group, a nitro group or a cyano group, and R₆Is hydrogen
Child or C₁~ C _FourIndicates an alkyl group. ) Is shown. 〕so
The N-aminopyrimidinedio according to claim 1 represented
Derivative. 3. A herbicide containing the N-aminopyrimidinedione derivative according to claim 1.