JP2000302764A - Phenyluracyl compound and its use - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a new phenyluracyl compound useful as a herbicide. SOLUTION: This compound is represented by formula I [R1 is H or a (substituted)1-6C alkyl; R2 is a 1-6C alkyl, a 3-6C alkenyl or a 3-6C alkynyl; and R3 is H or methyl]. The compound of formula I is obtained by reacting a carboxylic acid compound of formula II (e.g. 2-[2-chloro-4-fluoro-5- 3- methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl} phenoxy]- propionic acid) is reacted with a chlorinating agent such as thionyl chloride to afford an acid chloride, reacting the resultant acid chloride with an amino acid ester compound of formula III (e.g. glycine ethylester hydrochloride) in the presence of a base such as pyridine. The treating amount in using as a herbicide is preferably 1-8,000 g/ha. The compound can be used as a harvest auxiliary.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

TECHNICAL FIELD The present invention relates to a phenyluracil compound and a herbicide containing the same as an active ingredient.

[0002]

2. Description of the Related Art At present, many herbicides are commercially available and used. However, since weeds to be controlled are of many types and are long-term, they have a higher herbicidal effect and a broader herbicidal spectrum. However, there is a need for herbicides that do not cause phytotoxicity problems for crops. JP-A-63-41466 discloses that certain phenyluracil compounds have herbicidal activity, but these phenyluracil compounds do not have sufficient performance as herbicides.

[0003]

An object of the present invention is to provide a compound having excellent performance as a herbicide.

[0004]

Means for Solving the Problems The present inventors have conducted intensive studies to find a compound having excellent performance as a herbicide. As a result, a phenyluracil compound represented by the following general formula (2) has excellent performance as a herbicide. This led to the present invention. That is, the present invention provides a compound represented by the general formula

Embedded image [Wherein, R ¹ is a hydrogen atom, a C1-C6 alkyl group {the C
A 1-C6 alkyl group is a C1-C3 alkoxy group, a C1-
It may be substituted by a C3 alkylthio group, a C2-C4 alkoxycarbonyl group or an optionally substituted phenyl group. Wherein R ² represents a C1-C6 alkyl group, a C3-C6 alkenyl group or a C3-C6 alkynyl group, and R ³ represents a hydrogen atom or a methyl group. (Hereinafter, referred to as the present compound) and a herbicide containing the same as an active ingredient.

BEST MODE FOR CARRYING OUT THE INVENTION

The compound of the present invention has stereoisomers related to asymmetric carbon atoms, and each of them and a mixture thereof are included in the compound of the present invention. In the present invention, the C1-C3 alkoxy group, the C1-C3 alkylthio group, the C2-C4 alkoxycarbonyl group or the C1-C6 alkyl group optionally substituted by an optionally substituted phenyl group represented by R ¹ include: For example, methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, amyl group, isoamyl group, methoxymethyl group, ethoxymethyl group, 1-methoxyethyl group, 1-ethoxyethyl group, 2-methylthioethyl Group, methoxycarbonylmethyl group, 2-methoxycarbonylethyl group,
Examples include a phenylmethyl group and a (4-methoxyphenyl) methyl group. The C1-C6 alkyl group represented by R ^2, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, t- butyl group, amyl group, isoamyl group, t-amyl group, a hexyl group Examples of the C3-C6 alkenyl group include, for example, an allyl group, a 1-methyl-2-propenyl group, a 2-methyl-2-propenyl group, a 2-butenyl group, and a 3-butenyl group. And C3-C6 alkynyl groups include:
Examples include a propargyl group, a 1-methyl-2-propynyl group, a 1,1-dimethyl-2-propynyl group, a 2-butynyl group, a 3-butynyl group, and the like. Preferred substituents include those in which R ¹ is an isopropyl group or an isobutyl group.

The method for producing the compound of the present invention will be described. (Manufacturing method) Formula 3

Embedded image And a carboxylic acid compound represented by the general formula

Embedded image [Wherein, R ¹ and R ² represent the same meaning as described above. ] The method of producing from the amino acid ester compound shown by these. In the method, for example, an acid chlorinated product is obtained by reacting a carboxylic acid compound represented by the formula 3 with a chlorinating agent (hereinafter, referred to as an chlorinated product).
This is referred to as step 1. ), In the presence of a base, and by reacting with an amino acid ester compound represented by the general formula (hereinafter, referred to as step 2). Step 1 is performed without a solvent or in a solvent, and the reaction temperature is usually in the range of 0 to 15
0 ° C., and the reaction time is usually from instant to 24 hours. The theoretical amount of the reagent used in the reaction is 1 mole of the chlorinating agent to 1 mole of the carboxylic acid compound represented by the formula (3), but depending on the reaction conditions, it may be 1 mole to excess. Can be arbitrarily changed in the range of Examples of the chlorinating agent include thionyl chloride, sulfuryl chloride, phosgene, oxalyl chloride, phosphorus trichloride, phosphorus pentachloride, phosphorus oxychloride, and the like.Examples of the solvent include hexane, heptane, nonane, decane, ligroin, and cyclohexane. , Aliphatic hydrocarbons such as petroleum ether, aromatic hydrocarbons such as benzene, toluene, xylene, mesitylene, methylene chloride, chloroform, carbon tetrachloride, 1,
Aliphatic halogenated hydrocarbons such as 2-dichloroethane and 1,2,3-trichloropropane; aliphatic halogenated hydrocarbons such as monochlorobenzene, dichlorobenzene and benzotrifluoride; diethyl ether, diisopropyl ether and methyl-t -Butyl ether, 1,4
-Ethers such as dioxane, tetrahydrofuran and ethylene glycol dimethyl ether, and mixtures thereof. After completion of the reaction, the reaction solution is generally concentrated under reduced pressure, and the concentrated residue is used as it is as a raw material in step 2. Step 2 is performed in the presence of a base in the absence or presence of a solvent, and the reaction temperature is usually in the range of -20 to 100.
° C, and the reaction time is usually from instant to 24 hours. The amount of the reagent to be subjected to the reaction is based on 1 mole of the carboxylic acid compound represented by the formula 3 and the base and the formula 4
The theoretical amount of each of the amino acid ester compounds represented by is 1 mol, but depending on the reaction conditions,
It can be arbitrarily changed within the range of mol to excess.
As the base, for example, inorganic bases such as lithium hydrogen carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, lithium carbonate, sodium carbonate, potassium carbonate, pyridine, quinoline, 4-dimethylaminopyridine, 2-picoline, 3-
Picoline, 4-picoline, 2,3-lutidine, 2,4-
Lutidine, 2,5-lutidine, 2,6-lutidine, 3,
4-lutidine, 3,5-lutidine, 3-chloropyridine, 2-ethyl-3-methylpyridine, 5-ethyl-2
Nitrogen-containing aromatic compounds such as -methylpyridine, triethylamine, diisopropylethylamine, tri-n-propylamine, tri-n-butylamine, benzyldimethylamine, phenethyldimethylamine, N-methylmorpholine, 1,8-diazabicyclo [5. 4.0] Undec-7-ene, 1,5-diazabicyclo [4.3.
0] non-5-ene or tertiary amines such as 1,4-diazabicyclo [2.2.2] octane, and examples of the solvent include hexane, heptane, nonane, decane, ligroin, cyclohexane, and petroleum. Aliphatic hydrocarbons such as ethers, aromatic hydrocarbons such as benzene, toluene, xylene and mesitylene, methylene chloride,
Chloroform, carbon tetrachloride, 1,2-dichloroethane,
Aliphatic halogenated hydrocarbons such as 1,2,3-trichloropropane, monochlorobenzene, dichlorobenzene,
Examples thereof include aliphatic halogenated hydrocarbons such as benzotrifluoride, ethers such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, 1,4-dioxane, tetrahydrofuran, and ethylene glycol dimethyl ether, and mixtures thereof.
After completion of the reaction, the target compound of the present invention can be obtained, for example, by performing post-treatment operations by the following method. 1) The reaction solution is poured into water, extracted with an organic solvent, and the organic layer is dried and concentrated. 2) Concentrate the reaction solution as it is or, if necessary, filter and concentrate the filtrate. In addition, the compound of the present invention can be purified by operations such as chromatography and recrystallization. The amino acid ester compound represented by the general formula (4) may be available as its hydrochloride in such a case.
The amino acid ester compound shown in Chemical formula 4 can be used for the reaction after the reaction, but the reaction can also be carried out while neutralizing with a base in the reaction solution.

The method for producing the compound of the present invention from the carboxylic acid compound represented by the formula (3) and the amino acid ester compound represented by the formula (6) is not limited to the above-mentioned method, but includes a condensing agent (for example, carbonyldiimidazole). , Dicyclohexylcarbodiimide, etc.).

The carboxylic acid compound represented by the formula 3 is
-[2-Chloro-4-fluoro-5- {3-methyl-
2,6-dioxo-4- (trifluoromethyl) -1,
Ethyl 2,3,6-tetrahydropyrimidin-1-yl {phenoxy] propionate (JP-A-63-41466)
Can be produced by acid hydrolysis of a compound known in Japanese Patent Application Publication No. The amino acid ester compound represented by the general formula (4) is a compound known per se,
Alternatively, it can be produced from a commercially available α-amino acid by a known method.

The compound of the present invention has excellent herbicidal activity,
In addition, excellent selectivity between crops and weeds can be exhibited. For example, the compound of the present invention has a herbicidal effect on various weeds, which are the following problems, in foliage treatment and soil treatment in a field. Polygonum convolvulus (Polygonum convolvulus), Polygonum
gonum lapathiolium), Polygonum
pensylvanicum), haradade (Polygonum persicaria), stag beetle (Rumex crispus), sedge beetle (Rumex
obtusifolius), knotweed (Polygonum cuspidatum), purslaneaceae weed, purslane (Portulaca oleracea), sarcophagidaceae weed, Stellaria media, akazaceae weed, Chenopodium album, Koukia scopari
a) Amaranthus retroflexus, Amaranthus hybridus, Brassica weed Wild radish, Raphanus raphanistrum, Sinapis arvensis, Capsella bursa
-Pastoris) Legume weeds Sesbania exaltata, Cassia obtusifolia, Florida begerweed (Des
modium tortuosum), white clover (Trifoliumrepens) Malvaceae weed, Abutilon theophrasti, American deer
(Sida spinosa) Violet weeds Field pansies (Viola arvensis), wild pansies (Viola tricolor) Rubiaceae weeds Yamgra (Galium aparine) Convolvulaceae weeds
omoea hederacea var integriuscula)
(Ipomoea lacunosa), Convolvulus
arvensis) Labiatae Weed, Lamium purpureum, Photohenosa (Lam
ium amplexicaule) Solanaceae weed White Datura (Datura stramonium), Sornumnigrum (Solanumnigrum)
(Veronica hederaefolia) Asteraceae weed, Xanthium pensylvanicum, wild sunflower (Hel
ianthus annuus), dog chamomile (Matricaria perforata)
or inodora), corn marigold (Chrysanthemum s
egetum), orang (Matricaria matricarioides),
Ragweed (Ambrosia artemisiifolia), Oobtaxa (Am
brosia trifida) and Erigeron canaden
sis), Artemisia princeps, Artemisia princeps, Solidago altissima (Echinochloa crus-galli), Enokorogosa (Se
taria viridis), Achinoekorogosa (Setaria faber
i), crabgrass (Digitaria sanguinalis), crabgrass (Eleu
sine indica), Poa annua, Blackgrass (Alopecurus myosuroides), Oats (Avena)
fatua), sorghum sorghum (Sorghum halepense), silvergrass (Agropyron repens), and Umanohashiki (Bromus tect)
orum), Cynodon dactylon, Panax dichotomiflorum, Texas Panicum
cum texanum), shatter cane (Sorghum vulgare), astragalidae communis (Commelina communis), ascendaceae weed (Equisetum arvense), Cyperus iria (Cyperus iria), Cyperus (Cyperus)
rotundus), yellow bean sedge (Cyperus esculentus) and some of the compounds of the present invention
(Zea mays), wheat (Triticum aestivum), barley
(Hordeum vulgare), rice (Oryza sativa), sorghum
(Sorghum bicolor), soybean (Glycine max), cotton (Gos
sypium spp.), sugar beet (Beta vulgaris), peanuts (Arachis hypogaea), sunflowers (Helianthus annuu)
s), and does not show any phytotoxicity that could cause problems for major crops such as rapeseed (Brassica napus) and horticultural crops such as flowers and vegetables. In addition, the compound of the present invention can effectively eliminate various weeds which are problematic in non-tillage cultivation of soybean, corn, wheat and the like. Moreover, some of the compounds of the present invention do not exhibit any harmful effects on crops.

In addition, the compound of the present invention has a herbicidal effect on various weeds, which are the following problems, in flooding treatment of paddy fields. Grass weed Raspberry (Echinochloa oryzicola) Scrophulariaceae weed Azena (Lindernia procumbens) Scrophulariaceae weed Rixala (Rotala indica)
multiflora) Dipterocarpaceae Weedweed (Elatine triandra) Cyperaceae Weed Cyperus difformis, Firefly (Scirpu
s juncoides), pine stalks (Eleocharis acicularis), Spodoptera cricket (Cyperus serotinus), Krogwai (Eleocha)
ris kuroguwai) Mallow Mallow Weed Konagi (Monochoria vaginalis) Omodaka Weed Urikawa (Sagittaria pygmaea), Omodaka (Sagittar
ia trifolia), Spider-moth (Alisma canaliculatum) Hime-shiro (Potamogeton distinctus) Apiaceae weed Seri (Oenanthe javanica) In addition, some of the compounds of the present invention do not show any harmful effects on transplanted rice. . In addition, the compounds of the present invention may be used in orchards, pastures, lawns, forestry or waterways,
A wide range of weeds that can be found on canals or other non-crop lands. The compound of the present invention has a herbicidal effect on aquatic weeds such as water hyacinth (Eichhornia crassipes) which occur in waterways, canals and the like. The compound of the present invention has the same properties as the herbicidal compound described in International Patent Application Publication No. WO95 / 34659, and is introduced by introducing the herbicide resistance gene and the like described in the specification. In the case of cultivating a crop to which tolerance has been imparted, the compound of the present invention can be used in a larger dose than that used when cultivating a normal crop to which tolerance has not been imparted. Can be weeded.

When the compound of the present invention is used as an active ingredient of a herbicide, it is usually mixed with a solid carrier, a liquid carrier, a surfactant, and other pharmaceutical auxiliaries to prepare an emulsion, a wettable powder, a suspending agent,
Formulated in granules, concentrated emulsions, wettable powders and the like. These preparations contain the compound of the present invention as an active ingredient in a weight ratio of 0.001 to 80%, preferably 0.005 to 70%.
contains. As a solid carrier, kaolin clay, attapulgite clay, bentonite, acid clay, pyrophyllite, talc, diatomaceous earth, mineral powder such as calcite,
Organic substance fine powders such as walnut shell powder, water-soluble organic substance fine powders such as urea, inorganic salt fine powders such as ammonium sulfate, and fine powders of synthetic hydrous silicon oxide, and the like.
Aromatic hydrocarbons such as alkylbenzenes such as methylnaphthalene, phenylxylylethane and xylene; alcohols such as isopropanol, ethylene glycol and 2-ethoxyethanol; esters such as dialkyl phthalate; acetone, cyclohexanone and isophorone Ketones, mineral oils such as machine oil, vegetable oils such as soybean oil, cottonseed oil, dimethyl sulfoxide, N, N-dimethylformamide, acetonitrile, N-methylpyrrolidone,
Water and the like. Surfactants used for emulsification, dispersion, wet spreading, etc. include alkyl sulfates, alkyl sulfonates, alkyl aryl sulfonates,
Anionic surfactants such as dialkyl sulfosuccinate, polyoxyethylene alkyl aryl ether phosphate ester salt, polyoxyethylene alkyl ether, polyoxyethylene alkyl aryl ether, polyoxyethylene polyoxypropylene block copolymer, sorbitan fatty acid ester, poly Nonionic surfactants such as oxyethylene sorbitan fatty acid esters and the like can be mentioned. Other auxiliaries for formulation include lignin sulfonate, alginate, polyvinyl alcohol, gum arabic, CMC (carboxymethylcellulose), PAP
(Acidic isopropyl phosphate).

The compound of the present invention is usually formulated and subjected to soil treatment, foliage treatment or flooding treatment before or after emergence of weeds. Soil treatment includes soil surface treatment, soil admixture treatment, etc.For foliage treatment, in addition to treatment from above the plant,
There is a local treatment for treating only weeds so as not to adhere to crops.

When the compound of the present invention is used as an active ingredient of a herbicide, the amount of treatment varies depending on weather conditions, preparation form, treatment time, treatment method, soil conditions, target crops, target weeds, and the like. Usually 0.01g-1
000 g, preferably 1 g to 8000 g. Emulsions, wettable powders, suspensions, concentrated emulsions, wettable powders and the like are usually prepared in an amount of 10 to 1000 liters per hectare (if necessary, spreading). The mixture is diluted with water (to which an auxiliary agent or the like has been added) and treated, and granules and certain suspending agents are usually treated without any dilution. Here, as an auxiliary agent used as necessary, in addition to the above-mentioned surfactant, polyoxyethylene resin acid (ester), lignin sulfonate, abietic acid salt, dinaphthylmethane disulfonate, crop oil concentrate (Crop oil concentrate), soybean oil, corn oil,
Vegetable oils such as cottonseed oil and sunflower oil;

The compound of the present invention can be used as an active ingredient of a harvesting aid such as a cotton defoliant / desiccant or a potato (Solanum tuberosum) desiccant. In this case, the compound of the present invention is usually formulated in the same manner as when used as an active ingredient of a herbicide, and foliage treatment is performed alone or in combination with other harvesting aids before harvesting the crop.

[0015]

EXAMPLES The present invention will be described in more detail with reference to Production Examples, Formulation Examples and Test Examples, but the present invention is not limited to these Examples. First, Production Examples of the compound of the present invention will be shown. Production Example 1 2- [2-chloro-4-fluoro-5- {3-methyl-
2,6-dioxo-4- (trifluoromethyl) -1,
1.0 g of 2,3,6-tetrahydropyrimidin-1-yl {phenoxy] propionic acid was added to 1,4-dioxane 1
The mixture was dissolved in 0 ml, 1.0 ml of thionyl chloride was added, and the mixture was heated and stirred under reflux conditions for 1 hour. Thereafter, the reaction solution was concentrated as it was, and the obtained residue was diluted with 6 ml of 1,4-dioxane.
(Hereinafter referred to as solution A). On the other hand, 2 ml of 1,4-dioxane, 0.5 g of glycine ethyl ester hydrochloride, 0.5 ml of pyridine, and 0.2 g of potassium carbonate were placed in another container, and 1/3 of the solution A was added thereto at room temperature. For 30 minutes. Thereafter, the reaction solution was filtered, the filtrate was concentrated, and the obtained residue was subjected to preparative thin-layer chromatography (developing solvent: hexane / ethyl acetate = 2/1) to give a compound of the formula

Embedded image (Compound 1 of the present invention) was obtained in an amount of 0.06 g. ¹ H-NMR (CDCl ₃ , 300 MHz): δ (pp
m) 7.34 (1H, d, J = 8.8 Hz), 7.13
(1H, brs), 6.84 (1 / 2H, d, J = 6.
4Hz), 6.83 (1 / 2H, d, J = 6.3H)
z), 6.36 (1 / 2H, s), 6.35 (1/2
H, s), 4.68 to 4.63 (1H, m), 4.25
~ 4.03 (4H, m), 3.55 (3H, q, J =
1.1 Hz), 1.63 (3H, d, J = 6.8H)
z), 1.28 (3H, t, J = 7.9 Hz)

Production Example 2 2- [2-chloro-4-fluoro-5- {3-methyl-
2,6-dioxo-4- (trifluoromethyl) -1,
1.0 g of 2,3,6-tetrahydropyrimidin-1-yl {phenoxy] propionic acid was added to 1,4-dioxane 1
The mixture was dissolved in 0 ml, 1.0 ml of thionyl chloride was added, and the mixture was heated and stirred under reflux conditions for 1 hour. Thereafter, the reaction solution was concentrated as it was, and the obtained residue was diluted with 6 ml of 1,4-dioxane.
(Hereinafter referred to as solution A). Meanwhile, 2 ml of 1,4-dioxane, 0.5 g of L-leucine methyl ester hydrochloride, 0.5 ml of pyridine and 0.2 g of potassium carbonate were placed in another container, and 1/3 of the solution A was added thereto at room temperature. The mixture was left at room temperature for 1 hour and 30 minutes. Thereafter, the reaction solution was filtered, the filtrate was concentrated, and the obtained residue was separated by preparative thin-layer chromatography (developing solvent: hexane / ethyl acetate = 2).
/ 1) and the formula 6

Embedded image (Compound 2 of the present invention) (0.25 g) was obtained. ¹ H-NMR (CDCl ₃ , 300 MHz): δ (pp
m) 7.35 (1H, d, J = 8.8 Hz), 7.10
-6.95 (1H, m), 6.89-6.79 (1H,
m), 6.36 (1 / 2H, s), 6.35 (1/2
H, s), 4.70-4.55 (2H, m), 3.76
(1/2 × 3H, s), 3.69 (1/2 × 3H, s)
), 3.55 (3H, q, J = 1.2 Hz), 1.8
0 to 1.50 (3H, m), 1.62 (1 / 2H, d,
J = 6.7 Hz), 1.61 (1 / 2H, d, J = 6.
7 Hz), 0.98 to 0.88 (6H, m)

Production Example 3 2- [2-chloro-4-fluoro-5- {3-methyl-
2,6-dioxo-4- (trifluoromethyl) -1,
1.25 g of 2,3,6-tetrahydropyrimidin-1-yl {phenoxy] propionic acid was dissolved in 10 ml of 1,4-dioxane, and 1.0 ml of thionyl chloride was added.
The mixture was heated and stirred under reflux conditions for an hour. Thereafter, the reaction solution was directly concentrated, and the obtained residue was treated with 1,4-dioxane (8 m).
1 (hereinafter referred to as solution B). On the other hand, 2 ml of 1,4-dioxane, 0.5 g of L-valine methyl ester hydrochloride, 0.5 ml of pyridine and 0.2 g of potassium carbonate were placed in another container, and 1/4 of the solution B was added thereto at room temperature. The mixture was left at room temperature for 2 hours and 30 minutes. Thereafter, the reaction solution was filtered, the filtrate was concentrated, and the obtained residue was separated by preparative thin-layer chromatography (developing solvent: hexane / ethyl acetate = 2).
/ 1) and the formula 7

Embedded image (Compound 3 of the present invention) was obtained in an amount of 0.21 g. ¹ H-NMR (CDCl ₃ , 300 MHz): δ (pp
m) 7.36 (1H, d, J = 8.8 Hz), 7.25
-7.05 (1H, m), 6.86-6.80 (1H,
m), 6.35 (1H, t, J = 1.8 Hz), 4.7
1-4.65 (1H, m), 4.55-4.50 (1
H, m), 3.76 (１ ／ × 3H, s), 3.70
(1/2 × 3H, s), 3.56 (1/2 × 3H, br)
s), 3.54 (1/2 x 3H, brs), 2.35
２．１2.10 (1H, m), 1.63 (3H, d, J = 6.
6 Hz), 1.00 to 0.84 (6H, m)

Production Example 4 2- [2-chloro-4-fluoro-5- {3-methyl-
2,6-dioxo-4- (trifluoromethyl) -1,
2,3,6-tetrahydropyrimidin-1-yl {phenoxy] propionic acid (1.0 g) was added to tetrahydrofuran 6
and thionyl chloride (1 ml) was added with stirring.
The mixture was heated and stirred under reflux conditions for 10 minutes. Thereafter, the reaction solution was allowed to cool, and the reaction solution was concentrated as it was, and tetrahydrofuran 6 m
1 (hereinafter referred to as solution C). On the other hand, 6 ml of tetrahydrofuran and 0.49 g of L-methionine methyl ester hydrochloride were added to another container, 0.34 g of potassium carbonate and 0.35 ml of pyridine were added with stirring, and 3.5 g of solution C was further added at room temperature. Stirred at room temperature for 10 hours. Thereafter, ice water was added to the reaction solution, ethyl acetate and saturated saline were added, and the mixture was separated. The organic layer was washed with saturated saline, dried over magnesium sulfate, and concentrated. The residue was subjected to silica gel column chromatography (developing solvent: hexane / ethyl acetate = 1/1) to give the compound of formula 8

Embedded image (Compound 4 of the present invention) (0.60 g) was obtained. ¹ H-NMR (CDCl ₃ , 300 MHz): δ (pp
m) 7.35 (1H, d, J = 8.7 Hz), 7.30
(1H, brs), 6.87 (1 / 4H, d, J = 6.
3 Hz), 6.85 (1 / 4H, d, J = 6.4H)
z), 6.80 (1 / 2H, d, J = 6.3 Hz),
6.35 (1 / 2H, s), 6.34 (1 / 2H, s)
s), 4.76 to 4.63 (2H, m), 3.78 (1
/ 2 × 3H, s), 3.72 (1/2 × 3H, d, J =
1.2Hz), 3.55 (3H, t, J = 1.2H)
z), 2.54 (1/2 × 2H, t, J = 7.4H)
z), 2.47 to 2.40 (1/2 × 2H, m);
25-2.00 (2H, m), 2.04 (3H, s),
1.63 (１ ／ × 3H, d, J = 7.00 Hz),
1.62 (1/2 x 3H, d, J = 6.8 Hz)

Next, a method for producing a starting compound of the compound of the present invention will be described as a reference production example. Reference Production Example 1 2- [2-chloro-4-fluoro-5- {3-methyl-
2,6-dioxo-4- (trifluoromethyl) -1,
23,46 g of ethyl 2,3,6-tetrahydropyrimidin-1-yl {phenoxy] propionate is dissolved in 100 ml of 1,4-dioxane, and 50 ml of water and concentrated hydrochloric acid 5 are dissolved.
0 ml was added, and the mixture was heated and stirred under reflux conditions for 2 hours and 30 minutes. Thereafter, the reaction solution was allowed to stand at room temperature overnight, then, ethyl acetate and water were added, and the mixture was separated. The organic layer was washed with saturated saline, dried over magnesium sulfate, and concentrated. The residue was subjected to silica gel column chromatography (developing solvent:
Hexane / ethyl acetate = 3/1 to 1/2) to give 2-
[2-chloro-4-fluoro-5- {3-methyl-2,
6-dioxo-4- (trifluoromethyl) -1,2,2
13.07 g of 3,6-tetrahydropyrimidin-1-yl {phenoxy] propionic acid was obtained. ¹ H-NMR (CDCl ₃ , 300 MHz): δ (pp
m) 7.32 (1H, d, J = 8.8 Hz), 6.86
(1 / 2H, d, J = 6.2 Hz), 6.84 (1/2
H, d, J = 6.1 Hz), 6.35 (1 / 2H,
s), 6.33 (1 / 2H, s), 4.65 to 4.7
5 (1H, m), 3.54 (3 / 2H, s, br),
3.52 (3 / 2H, s, br), 1.66 (3H,
d, J = 6.9 Hz)

Next, preparation examples are shown. Formulation Example 1 50 parts of each of the compounds of the present invention, 3 parts of calcium ligninsulfonate, 2 parts of sodium lauryl sulfate and 45 parts of synthetic hydrous silicon oxide are thoroughly pulverized and mixed to obtain each wettable powder. Formulation Example 2 5 parts of each of the compounds of the present invention, 14 parts of polyoxyethylenestyrylphenyl ether, 6 parts of calcium dodecylbenzenesulfonate, 37.5 parts of xylene and 37.5 parts of cyclohexanone are mixed well and each emulsion is prepared. obtain. Formulation Example 3 2 parts of the compound of the present invention, 2 parts of synthetic hydrous silicon oxide, 2 parts of calcium ligninsulfonate, 30 parts of bentonite and 64 parts of kaolin kure are well pulverized and mixed, water is added and kneaded well, followed by granulation. Dry to obtain each granule. Formulation Example 4 25 parts each of the compound of the present invention, polyvinyl alcohol 10
% Aqueous solution and 25 parts of water are mixed and wet-pulverized until the average particle size becomes 5 μm or less to obtain each suspending agent. Formulation Example 5 5 parts of each of the compounds of the present invention are added to 40 parts of a 10% aqueous solution of polyvinyl alcohol, and the mixture is emulsified and dispersed with a homogenizer until the average particle diameter becomes 10 μm or less. Water is added to obtain each concentrated emulsion.

Next, Test Examples show that the compounds of the present invention are useful as active ingredients of herbicides. Evaluation of herbicidal efficacy
“0” indicates that the growth state of the test plant (weed) at the time of the survey was completely or hardly different from that of the untreated plant
And, the test plant is completely dead or growth is completely suppressed as "5", and classified into six stages of "0" to "5", "0", "1", "2", Indicated by “3”, “4” or “5”. Evaluations of herbicidal efficacy “4” and “5” indicate excellent herbicidal efficacy, and evaluations of “3” or less indicate insufficient herbicidal efficacy.

Test Example: Field foliage treatment test Field soil was packed in a plastic pot having an area (26.5 × 19) cm ² and a depth of 7 cm, and a fir tree was sown and grown in a greenhouse for 21 days. A test compound was used as an emulsion according to Formulation Example 2, and a predetermined amount thereof was diluted with water containing 1% of agridex equivalent to 1000 liters per hectare,
It was evenly sprayed over the whole foliage from above the plant using a small sprayer. After the treatment, the plants were grown in a greenhouse for 24 days, and the herbicidal efficacy was evaluated. Table 1 shows the results.

[Table 1]

By using the compound of the present invention, an excellent herbicidal effect can be obtained.

Claims (3)

[Claims] 1. A compound represented by the general formula: [Wherein, R ¹ is a hydrogen atom, a C1-C6 alkyl group {the C
A 1-C6 alkyl group is a C1-C3 alkoxy group, a C1-
It may be substituted by a C3 alkylthio group, a C2-C4 alkoxycarbonyl group or an optionally substituted phenyl group. Wherein R ² represents a C1-C6 alkyl group, a C3-C6 alkenyl group or a C3-C6 alkynyl group, and R ³ represents a hydrogen atom or a methyl group. A phenyluracil compound represented by the formula: 2. The phenyluracil compound according to claim 1, wherein R ³ is a methyl group. 3. A herbicide comprising the phenyluracil compound according to claim 1 as an active ingredient.