JPH0449279A - Herbicidal 2,4,6-trisubstituted aromatic heterocyclic compound - Google Patents

Abstract

NEW MATERIAL:The compound of formula I [X is -CH= or -N=; Y is halogen, OH, 1-4C alkoxy, alkylthio, etc.; R<1> is halogen, 1-4C alkyl, (1-4C haloalkyl- substituted) phenyl, (1-4C alkyl-substituted) pyridyl or 3-6C branched alkyl; R<2> is halogen, (1-4C haloalkyl-substituted) phenyl or 3-6C branched alkyl; with a proviso]. EXAMPLE:2-(4'-Chlorophenyl)-4-hydroxy-6-(2''-methylphenyl)pyrimidine. USE:An active component of herbicide. It kills all plants grown on undesirable area and acts as a non-selective or a selective herbicide according to the concen tration in use. PREPARATION:The compound of formula I wherein X is -N= and Y is OH can be produced by reacting a compound of formula II (R is lower alkyl) with a compound of formula III in an inert solvent (e.g. methanol) in the presence of an acid acceptor (preferably sodium methoxide, etc.).

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to novel 2,4,6-)-substituted aromatic heterocycles, their preparation and their use as herbicides.

Already before the filing date of the present application, 4-substituted-2,6-diphenylpyridine derivatives (Japanese Unexamined Patent Application Publication No. 64-72), 5-Fll-2
,4-diphenylpyrimidine derivatives (EP-A 035
4766) as a herbicidal compound, a pyridylpyrimidine derivative (JP-A No. 63-264478) as a plant disease control agent, and 2-tert-butyl-6-med-bovine diphenyl-4-methylthiopyridine [synthesis (Syn)] as a plant disease control agent.
theis) +1987, p839) and 2~
ter t-butyl-6 phenylpyridine [Heterocycles (Heter.

cy(les)+ vol. 3, pH 45, 1975).

The present inventors have now succeeded in synthesizing a 2,4,6-trisubstituted aromatic heterocycle represented by the following formula (J), and have discovered that the compound of formula (1) has herbicidal activity.

In the formula, X represents -CH= or -N-, and Y represents a halogen atom, a hydroxy group, an alkoxy group having 1-4 carbon atoms, an alkylthio group having 1-4 carbon atoms, or an alkyl group having 1-4 carbon atoms. represents an amino group, R1 is a phenyl group optionally substituted with halogen, alkyl having 1 to 4 carbon atoms or haloalkyl having 1 to 4 carbon atoms, pyridyl optionally substituted with alkyl having 1 to 4 carbon atoms; or a branched alkyl group having 3-6 carbon atoms, and R2 is a phenyl group optionally substituted with halogen or haloalkyl having 1-4 carbon atoms,
Or, it represents a branched alkyl group having 3-6 carbon atoms, provided that when X represents -CH=, R2 represents a branched alkyl group having 3-6 carbon atoms, and R1 and R1 simultaneously represent a phenyl group. When it represents, at least one of the phenyl groups has a substituent.

The compound of the formula (1) of the present invention can be produced, for example, by the following method: Production method a): [In the formula (1), X represents -N=, and Y
represents a hydroxy group] Formula: In the formula, R' is the same as above, and R represents a lower alkyl group. Production method b): [In formula (1), X represents -N=, and Y
represents a halogen atom] Formula: In the formula, R1 and R3 are the same as above, obtained by reacting a compound represented by and a halogenating agent, Production method C): [In formula (1), When X represents -N- and Y represents an alkoxy group having 1-4 carbon atoms or an alkylthio group having 1-4 carbon atoms, Y is Yl] Formula: In the formula, R1 and R1 are the same as above. , and M represents a halogen atom, and is obtained by reacting a compound represented by the formula: %formula%() in which Yl is the same as above, and manufacturing method d) : [In the formula (1), when X represents -CH- and Y represents a methylthio group 3 Formula: In the formula, R1 is the same as above, and a compound represented by: Formula: %Formula%() In the formula, Bz is the same as above and can be obtained by reacting with the compound represented by.

The 2.4.6-)-substituted aromatic heterocycle of formula (1) of the present invention exhibits good herbicidal activity.

In the compound of formula (1) of the present invention and each intermediate for producing the compound of formula (I) above, the halogen atom represents fluoro, chloro, bromo, or iodo, preferably fluoro, chloro, or bromo. particularly chlor.

The alkyl group having 1 to 4 carbon atoms, and the alkyl group having 1 to 4 carbon atoms in the alkoxy group having 1 to 4 carbon atoms, the alkylthio group, the alkylamino group, and the haloalkyl group are methyl, ethyl, propyl, 1so- Propyl, n-(i
so-, 5ec- or tert-)butyl, preferably methyl or ethyl.

Further, the lower alkyl group has the same definition as the alkyl group having 1 to 4 carbon atoms.

The halogen moiety of the haloalkyl group having 1 to 4 carbon atoms represents the same atoms as shown above, preferably represents fluoro or chloro, particularly represents fluoro, and the haloalkyl group preferably represents a trifluoromethyl group. show.

Branched alkyl having 3-6 carbon atoms is tso-propyl,
1so-butyl, 5ee-butyl, tert-butyl,
1so-pentyl, neopentyl, tert-pentyl, 1so-hexyl or 1-ethyl-1-methylpropyl, preferably tert-butyl.

In the compound of formula (1) of the present invention, preferable examples thereof include: X represents -CH= or -N=, Y is a halogen atom, a hydroxy group, an alkoxy group having 1-2 carbon atoms, 1-2 alkylthio group or C1-2 alkylamino group, R1 is a phenyl group optionally substituted with halogen, C1-2 alkyl, or trifluoromethyl, substituted with methyl a pyridyl group or a branched alkyl group having 4-6 carbon atoms, which may be substituted with a phenyl group or a branched alkyl group having 4-6 carbon atoms, in which R2 is optionally substituted with halogen or trifluoromethyl. group, and provided that when X represents -CH=, R- represents a carbon number of 4-
In the case where R1 and Rt both represent a phenyl group, at least one of the phenyl groups has a substituent.

Furthermore, particularly preferred examples include: X represents -CH- or -N=, Y represents a chlor atom, a hydroxy group, a methylthio group, and R1 is substituted with chloro, methyl or trifluoromethyl. a phenyl group or a tert-
represents a butyl group, provided that when X represents -CH=, Rz represents a tert-butyl group, and when R1 and R2 simultaneously represent a phenyl group, at least one of the phenyl groups has a substituent. can be given.

As specific examples of the compound of formula (I) of the present invention, the following compounds can be particularly exemplified.

2-(4′-chlorophenyl)-6-(2″-methylphenyl)-4-methylthiopyrimidine, 2-tert-
Butyl-6-(2'-methylphenyl)-4-methylthiopyridine, 2-tert-butyl-6-(2'-methylphenyl)
4-Methylthiopyrimidine.

In production method a), when 2'-methylbenzoylacetic acid ethyl ester and 4-chlorophenylguanidine are used as raw materials, the reaction formula is shown below.

In production method b), when 2-(4'-chlorophenyl)-4-hydroxy6-(2''-methylphenyl)pyrimidine and phosphorus oxychloride are used as raw materials, the reaction formula is expressed as below. .

R In production method C), as a raw material, for example, 4-chloro-2
When using -(4'-chlorophenyl)-4(2#-methylphenyl)pyrimidine and methylmercapto sodium, the reaction formula is expressed as below.

p In production method d), for example, 3.3-bis(
When methylthio)-1-(2'-methylphenyl)-2-propen-1-one and binacolon are used, the reaction formula is expressed as below.

In the above production method a), the compound of formula (I[) which is a raw material means a compound based on the above definitions of R1 and R, and preferably has the same meaning as the above preferred definition.

The compound of formula (I[) is well known in the field of organic chemistry, and a representative example thereof is ethyl 7methylbenzoylacetate.

In the above production method a), another raw material of formula (II)
The compound I) means a compound based on the above definition of R2, and preferably has the same meaning as the above preferred definition.

Compounds of formula (I[l) are described in European Patent Publication No. 169
72, etc., and a representative example thereof is 4-chlorophenylguanidine.

In the above production method b), the compound (Ia) as a raw material means a compound based on the above definitions of R1 and R, and preferably has the same meaning as the above preferred definition.

The compound of formula (Ia) can be obtained by the above production method a), and a representative example thereof is 2-(4'chlorophenyl)-4-hydroxy-6-(2'methylphenyl)pyrimidine.

In the above production method b), examples of the halogenating agent used include the following.

phosphorus oxychloride, phosphorus pentachloride, phosphorus oxybromide, and Phosphorous pentabromide.

In the above production method C), the compound of formula (Ib) which is a raw material means a compound based on the definitions of R', R'' and M above.

In formula (Ib), R1 and Rt preferably have the same meanings as the above preferred definitions, and M preferably represents chloro.

The compound of formula (Ib) can be obtained by the above production method b), and a typical example thereof is 4-chloro-2-(4'
-chlorophenyl)-4-C2"-methylphenyl)pyrimidine can be exemplified.

In the above production method C), the compound of formula (IV) which is a raw material means a compound based on the above definition of Yl.

In the compound of formula (IV), Yl preferably represents an alkoxy group having 1-2 carbon atoms or an alkylthio group having 1-2 carbon atoms.

The compound of formula (IV) is well known in the field of organic chemistry, and sodium methylmercapto is a typical example thereof.

In the above production method d), the compound of formula (V) as a raw material means one based on the definition of R1 above.

In the compound of formula (V), R1 preferably has the same meaning as the preferred definition above.

The compound of formula (V) can be prepared, for example, as described in the well-known publication Synthesis, 1987. Volume 9, p8
39-841, etc., and a representative example thereof is 3,3-bis(methylthio)-1-(2
An example is '-methylphenyl)-2-propen-1-one.

The compound of formula (VI), which is also a raw material, has the meaning based on the definition of Rt above.

In the compound of formula (Vl), R1 preferably has the same meaning as the preferred definition above.

The compound of formula (Vl) is well known in the field of organic chemistry, and a representative example thereof is binacolon.

When carrying out the above manufacturing method a), as a suitable diluent,
Mention may be made of all inert solvents.

Examples of such diluents include water: ethers such as dioxane, tetrahydrofuran, diethylene glycol methyl ester; alcohols such as methanol, ethanol, 1so-propanol, butanol, ethylene glycol; sulfones, sulfoxides such as dimethyl sulfoxide, Sulfolane: and bases such as pyridine.

Preparation method a) is preferably carried out in the presence of an acid binder, and examples of such acid binders include alkali metal hydroxides, carbonates, and alcolades.

Process a) can be carried out within a substantially wide temperature range. Generally, it can be carried out between about 20 and about 200'C, preferably between about 50 and 150'C. Also,
Although it is preferable to carry out various reactions under normal pressure, they can also be operated under increased pressure or reduced pressure.

In carrying out production method a), for example, for 1 mole of the compound of formula (It), the compound of formula (I[l) is added in an amount of 1 mole to 1.5 times mole in an inert solvent such as methanol. The target compound can be obtained by reacting in the presence of sodium methoxy in a molar amount to 2.4 times the molar amount.

When carrying out the above manufacturing method b), as a suitable diluent,
Mention may be made of all inert solvents.

Examples of such diluents include water; aliphatic, cycloaliphatic and aromatic hydrocarbons (optionally chlorinated) such as benzene, toluene, xylene, methylene chloride, chloroform, carbon tetrachloride. , ethylene chloride, chlorobenzene, dichlorobenzene: others,
can be mentioned.

Preparation method b) is preferably carried out in the presence of a catalyst, and N,N-dimethylaniline can be mentioned as an example of such a catalyst.

Process b) can be carried out within a substantially wide temperature range. Generally, it can be carried out between about 0 and about 200'C, preferably between about 20 and about 150'C. Further, although it is desirable that the various reactions be carried out under normal pressure, they can also be operated under increased pressure or reduced pressure.

In carrying out production method b), for example, a halogenating agent is added in an amount of 1 mole to 10 times the mole of the compound of formula (Ia), for example, in the presence of phosphorus oxychloride, which also serves as the halogenating agent and a solvent. The target compound can be obtained by the reaction.

When carrying out the above manufacturing method C), as a suitable diluent,
Mention may be made of all inert solvents.

Examples of such diluents include water; alcohols, e.g.
Examples include methanol, ethanol, 1so-propanol, butanol, and ethylene glycol.

Process C) can be carried out within a substantially wide temperature range. Generally, it can be carried out at a temperature between about 0 and about 150°C, preferably between about 20 and about 100°C. Further, although it is desirable that the various reactions be carried out under normal pressure, they can also be operated under increased pressure or reduced pressure.

In carrying out production method C), for example, the desired product can be obtained by reacting 1 mole of the compound of formula (Ib) with 1 to 2 times the mole of the compound of formula (mV) in an inert solvent such as methanol. compound can be obtained.

When carrying out the above manufacturing method d), as a suitable diluent,
Mention may be made of ethers such as di-1so-propyl ether, dibutyl ether, dioxane, tetrahydrofuran; and nitriles such as acetonitrile.

Process d) must be carried out in the presence of an acid binder, such as an alkali metal hydroxide, such as sodium methoxide, potassium tert- Mention may be made of butoxide.

Process d) can be carried out within a substantially wide temperature range. Generally, it can be carried out at a temperature between about 0 and about 200°C, preferably between about 20 and about 150°C. Further, although it is desirable that the various reactions be carried out under normal pressure, they can also be operated under increased pressure or reduced pressure.

When carrying out production method d), for example, the compound of formula (Vl) is added in an amount of 1 mol to 1 mol per 1 mol of the compound of formula (V).
．． The target compound can be obtained by reacting in 2 moles of an inert solvent such as tetrahydrofuran and acetic acid.

The active compounds according to the invention can be used as herbicides.

A weed is broadly defined as any plant that grows in an undesirable location.

The compounds of the invention act as non-selective or selective herbicides depending on the concentration used.

The active compounds according to the invention can be used, for example, with the following plants:

Genus of dicotyledonous weeds: Sinapis, Lepidium, Galium, Stella
ria), Chenopodiu
m), Urtica, Senecio, Amaranthus, Portulaca.

Portulaca, Portulaca (X
antiuw), morning glory (Ipos+oea), willow willow (Polygonum), ficus
rosia), Noa thistle/Fuji thistle (Cirsic)
v), Sonchus, Solanum, Rolippa,
Lamium, Veron ica, Da tura, Violet pansy
a), Ga 1eopsis, Poppy (
Papaver), Cornflower (Centaurea)
), Gal insoga, Rotala, Lindernia
and so on.

Genus of dicotyledonous plants: Gossypium,
Soybean (Glycine), Swiss chard/sugar beet (Beta), Carrot (Daucus), Kidney bean/Phaseolus, Pea (Pisum), Eggplant/Potato (Solanum)
, Linum, Sweet Potato/Morning Glory (Ipo)
moe), Vicia nandina (Vicia),
Tobacco (Nicotiana), Lyc
.

pers 1con), peanuts (Arach
is), Brassica, Chinese cabbage, turnip, cabbage (Br
assica), Lactuca,
Cucumber melon (Cucu menis), Capocha (Cu
curbita) etc.

Genus of monocot weeds: Echinocbloa,
Enkoro Awa (Setaria), Millet (Panic)
um), Digitaria, Phleum, Phleum, Poa, Poa, Digitaria (F
estuca), Eleusi
ne), Loliu+s, Bro*us, Oat (Avena), Cyperus °
Papyrus Cyperus,
Sorghum, Agrop
yron), Monochoria, Fimbristylis, Sagittaria, Eleocharjs, Scirpus, Pas
palu*), platypus (Ischaemuw), staghorn (AgrostiS), sparrowfly (Al
opeculus), Cynodon
)and so on.

Monocotyledonous cultivated plants [: rice (Oryza), corn/popcorn (Zea), wheat (Trit)
icum), barley (Hordeum), oat/oat (Avena), rye (Secale), sorghum (Sorghum)
um), millet (Panicus), sugarcane Saccharum, pineapple (Anan)
as), asparagus, green onion,
Chive (^111us) etc.

The use of the compounds of the present invention is not limited to the above-mentioned plants, but can be applied to other plants as well. Also,
Depending on the concentration used, the active compounds can control weeds non-selectively and can be used, for example, on industrial sites such as factories, railway tracks, roads and on plantations as well as non-plantation areas.

Furthermore, the active compounds can be used for weed control in perennial plant cultivation, for example in afforestation, ornamental plantations, orchards, vineyards, citrus orchards, nut orchards, banana cultivation bases, coffee cultivation bases, tea cultivation bases. It can be applied to rubber cultivation bases, Guinea oil palm plantations, cocoa cultivation bases, small orchards and hop cultivation fields, and for selective weed control in annual plant cultivation.

The active compounds according to the invention can be put into customary pharmaceutical forms. Such forms include liquids, emulsions,
Suspensions, permanent solutions, powders, foams, pastes, granules, aerosols, active compound infiltration - natural and synthetic, microcapsules, and UL [cold mist]
m1st), warm mist (war song-1st))
can be mentioned.

These formulations can be manufactured by known methods.

Such methods include, for example, combining the active compound with a developing agent, i.e.
This is carried out by mixing with liquid diluents; liquefied gas diluents; solid diluents or carriers, optionally surfactants, ie emulsifying agents and/or dispersants and/or foam formers.

When using water as a developing agent, for example, organic solvents can also be used as co-solvents.

As liquid diluent or carrier, aromatic hydrocarbons are generally used! (e.g., xylene, toluene, alkylnaphthalene, etc.), chlorinated aromatic or chlorinated aliphatic hydrocarbons (e.g., chlorobenzenes, ethylene chloride, methylene chloride, etc.), aliphatic hydrocarbons [e.g., cyclohexane, etc.] Paraffin I! (e.g., mineral oil fractions, etc.)], alcohols (e.g., butanol, glycols and their ethers, esters, etc.), ketones (e.g., acetone, methyl ethyl ketone, methyl isobutyl ketone, or cyclohexanone, etc.), strong polar solvents (e.g., dimethylformamide, dimethylsulfoxide, etc.) and water.

The liquefied gas diluent or carrier is a gas at normal temperature and pressure, and examples thereof include butane, propane, nitrogen gas,
Mention may be made of aerosol propellants such as carbon dioxide and halogenated hydrocarbons.

Solid diluents include soil natural minerals (e.g. kaolin, clay, talc, chalk, quartz, attapulgite,
montmorillonite or diatomaceous earth), soil synthetic minerals (for example, highly dispersed silicic acid, alumina, silicates, etc.).

Solid carriers for granules include crushed and fractionated rocks (e.g. calcite, marble, pumice, sepiolite, dolomite, etc.), synthetic piles of inorganic and organic materials, and organic materials (e.g. sawdust, Examples include fine grains of coconut (cobs of coconut, cobs of corn, stalks of tobacco, etc.).

Emulsifiers and/or foaming agents include nonionic and anionic emulsifiers [e.g., polyoxyethylene fatty acid esters, polyoxyethylene fatty acid alcohol ethers (e.g., alkylaryl polyglycol ethers, alkyl sulfones ML alkyl sulfates, aryl sulfonates); etc.)] and albumin hydrolysis products.

Examples of dispersants include lignin sulfide waste liquid,
and includes methylcellulose.

Adhesives can also be used in the formulation (powders, granules, emulsions), such adhesion agents include carboxymethylcellulose and natural and synthetic polymers such as gum arabic, polyvinyl alcohol and polyvinyl acetate. I can do it.

Coloring agents may also be used, such as:
Il-free pigments (such as iron oxide, titanium oxide and Prussian blue) and organic dyes such as alizarin dyes, azo dyes or metal phthalocyanine dyes and also iron,
Mention may be made of such trace elements as manganese, poron, copper, cobalt, molybdenum, their salts of zinc.

The formulations may generally contain from 0.1 to 95% by weight, preferably from 0.5 to 90% by weight of said active ingredient.

The active compounds according to the invention can be used on their own or in their formulation form for weed control, and also as a mixture with known herbicides, such mixtures being suitable for the final formulation. Or tank mix is possible.

Possible combinations as a mixture include, for example, the following known herbicides.

4-Amino-6 for weed control in grain cultivation
-(1,1-dimethylethyl)-3-ethylthio-1,
2,4-)riazin-5(4H)-one, 1-amino-
6-ethylthio 3-(2,2 dimethylpropyl,
3.5-triazine 2.4 (IH,3H)-dione,
or N-(2-benzothiazolyl)-N,N'-dimethylurea, etc.; 4-amino-3-methyl-6-phenyl-1,2,4 for weed control in sugarcane cultivation.
triazin-5(4H)-one, etc.; 4-amino 6-one for weed control in soybean cultivation;
(1,1-dimethylethyl)-3-methylthio-1,2
, 4-) riazin-5(4H)-one, and so on.

Surprisingly, some mixtures of the compounds of the invention also exhibit synergistic effects.

When using the active compounds of the invention, they can be used directly as such, or in the form of formulations such as spray preparations, emulsions, suspensions, powders, pastes and granules, or prepared in further dilutions. It can be used in the following manner.

The active compounds can be used by watering, spraying, dusting, etc.

The active compounds of the invention can be used both before and after germination of plants. Also, before sowing,
It can also be incorporated into the soil.

The concentration of active compound can vary within a substantial range. It differs fundamentally depending on the nature of the desired effect. When used as a herbicide, the concentration used is, for example, about 0.1 as active compound per hectare.
~10 kg, preferably about 0.2~5 kg.

Next, the production and use of the compound of the present invention will be specifically illustrated by the following examples, but the present invention should not be limited thereto.

Production example: Example 1 0 ■ Sodium methoxide (4.3 g) in methanol (8 (
ld) Add 7-methylbenzoylacetic acid ethyl ester (14.8 g) to the solution and stir at room temperature for 15 minutes. 4-chlorophenylguanidine (10.8 g) was added to this solution and heated under reflux for 20 hours.

After the reaction, the solvent is distilled off under reduced pressure, water is added to the residue, and the mixture is neutralized with dilute hydrochloric acid. The formed crystals were collected by filtration and recrystallized with ethanol to give 2-(4'-chlorophenyl)4-hydroxy-6-(2"-methylphenyl)pyrimidine (16,3
g) is obtained.

sp, 254-25 6.5°C Example 2 I After the reaction is heated to reflux for 40 minutes, excess phosphorus oxychloride is removed under reduced pressure. The residue is dissolved in chloroform (60d), poured onto ice (approximately 100 g) and neutralized with aqueous ammonia. Remove the organic layer and add chloroform (50%)
When the residue was purified by silica gel column chromatography (eluent: ether), 4-chloro-2-(
4'-chlorophenyl)-4-(2"-methylphenyl)pyrimidine (5,6 g) is obtained.

MP, 112-113°C Example 3 2-(4'-chlorophenyl)-4-hydroxy-6-
(2”-methylphenyl)pyrimidine (5.8 g) was added to phosphorus oxychloride (20d) at room temperature and 4-chloro-
Methylmercapto sodium (15%) was added to a methanol solution of 1-(4'-chlorophenyl)-4-(2''-methylphenyl)pyrimidine (1,56 g), and the mixture was heated under reflux for 3 hours, followed by a reaction under reduced pressure. Concentrate and extract twice with dichloromethane (30d). After drying over anhydrous magnesium sulfate, the solvent is distilled off under reduced pressure, and the residue is purified by silica gel column chromatography to yield 2-(4'-chlorophenyl)-4-methyl. Mercapto-6-(2''-methylphenyl)pyrimidine (1,40 g) is obtained.

Example 4 (3.85 g) and vinegar r71i (50I11) were heated at 90-93°C and THF was distilled off. After this, reflux for 5 hours,
Concentrate under reduced pressure. Add a small amount of water to the residue, make it alkaline with potassium carbonate, and extract twice with dichloromethane (3(ld)). After drying over anhydrous potassium carbonate, the solvent is distilled off under reduced pressure, and the residue is purified by silica gel column chromatography. Oily 2-tertbutyl-4-methylmercapto-6-(2'-methylphenyl)pyridine (0,
86 g) is obtained.

'HNMR (60MHz, CDCl5), δ(
ppm) 1.37 (9H,s, C(CHs)
i) Potassium tert-butoxide (1.35 g) is added to tetrahydrofuran (THF) (3 (ld)), to which is added vinacolon <0.50 g, and the mixture is stirred at room temperature for 30 minutes. Add 3.3-bis(methylthio)-1 to this solution.
Add -(2'-methylphenyl)-2-propen-1-one (1.43 g) and stir at room temperature for 1 hour.
Add 2.46 ammonium acetate (3H, s,
S CHi )6.87~7.43 (6)1
．． m) Compounds that can be obtained by the same method as in Examples 1 to 4 above are shown in Table 1 below together with the compounds produced in the above Examples.

Biological test example: The herbicidal efficacy shown below is determined by observing the growth state of the test plants during the survey, and determining whether the growth state is the same or almost the same as that of the plants in the untreated (no compound treated) area. Shimono,
The evaluation is ``0'', and those that do not wither or whose growth is completely inhibited are evaluated as rloOJ, and are evaluated as percent control.

Test Example 1 Field weed foliage treatment test Preparation of active compound Carrier: 5 parts by weight of acetone Emulsifier: 1 part by weight of benzyloxypolyglycol ether Preparation of active compound The drug was 1 part by weight of the active compound and the above amounts of carrier and emulsifier. It is obtained as an emulsion by mixing. A predetermined amount of the drug is prepared by diluting it with water.

Test method: In a greenhouse, rice (variety:
The soil mixed with seeds of Nipponbare) was covered to a depth of 1 cm. The plants were grown in a greenhouse for 10 days, and then a predetermined amount of the above-prepared chemical solution was uniformly sprayed onto the stems and leaves of the test plants in each test pot. Efficacy was determined 3 weeks after treatment.

The results are shown in Table 2.

Table 2 Test Example 2 Pre-germination soil treatment test for upland weeds In a greenhouse, seeds of field field weed, green field weed, and rice (variety: Nipponbare) for direct sowing were mixed into 500c+*” pots filled with field soil. The soil was covered to a depth of 1 cm. One day later, a predetermined amount of the chemical solution prepared in the same manner as in Test Example 1 was uniformly sprayed on the soil surface layer of each test pot. Efficacy was determined 4 weeks after treatment. The results are shown in Table 3.

The water surface was treated with a pipette. Thereafter, a warm water condition of about 3 cm was maintained, and the efficacy was determined 4 weeks after the drug treatment. The results are shown in Table 4.

Table Test Example 3 Efficacy test 1 against paddy weeds /2.000 are pot (25X20X9cm
) was filled with paddy soil, and three rice seedlings (variety: Nipponbare) at the 2.5 leaf stage (plant height approximately 715 cm) were planted per pot and transplanted in two locations. In addition, Japanese grasshopper, Japanese cypress, bulrush, and annual broad-leaved weeds (Azaena,
Kikashigusa, Japanese Chickweed, Japanese Chickweed, Japanese Chickweed, etc.)
Seeds were sown and kept moist. Approximately 2-3c after 2 days
After flooding and 5 days after transplanting paddy rice, in the table of prescribed amount of chemical solution prepared in the same manner as in Test Example 1, A: Novie C: Firefly E: Broad-leaved weed

Claims (4)

[Claims] (1) Formula: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ In the formula, X represents -CH= or -N=, Y is a halogen atom, hydroxy group, alkoxy group having 1-4 carbon atoms, carbon represents an alkylthio group having 1-4 carbon atoms or an alkylamino group having 1-4 carbon atoms, and R^1 is phenyl optionally substituted with halogen, alkyl having 1-4 carbon atoms, or haloalkyl having 1-4 carbon atoms; group, a pyridyl group optionally substituted with alkyl having 1 to 4 carbon atoms, or a branched alkyl group having 3 to 6 carbon atoms, and R^2 is substituted with halogen or haloalkyl having 1 to 4 carbon atoms. represents a phenyl group or a branched alkyl group having 3 to 6 carbon atoms, which may be
-6 represents a branched alkyl group, and R^1 and R^2
2,4,6-trisubstituted aromatic heterocycles represented by: when simultaneously represents a phenyl group, at least one of the phenyl groups has a substituent. (2) X represents -CH= or -N=, Y represents a halogen atom, a hydroxy group, an alkoxy group having 1-2 carbon atoms, or an alkylthio group having 1-2 carbon atoms, and R^1 is , represents a phenyl group optionally substituted with halogen, an alkyl group having 1 to 2 carbon atoms or trifluoromethyl, a pyridyl group optionally substituted by methyl, or a branched alkyl group having 4 to 6 carbon atoms, and R ^2 represents a phenyl group which may be substituted with halogen or trifluoromethyl, or a branched alkyl group having 4-6 carbon atoms. However, when x represents -CH=, R^2 is Carbon number 4
-6 represents a branched alkyl group, and R^1 and R^2
2. The compound according to claim 1, wherein when simultaneously represents a phenyl group, at least one of the phenyl groups has a substituent. (3) X represents -CH= or -N=, Y represents a chlor atom, hydroxy group, or methylthio group, and R^1 is phenyl optionally substituted with chlor, methyl, or trifluoromethyl; or a tert-butyl group, and R^2 represents a phenyl group or a tert-butyl group optionally substituted by fluoro, chloro or trifluoromethyl, provided that when X represents -CH=, R^2 is tert
-butyl group, and when R^1 and R^2 simultaneously represent a phenyl group, at least one of the phenyl groups has a substituent. (4) Formula: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ In the formula, X represents -CH= or -N=, Y is a halogen atom, hydroxy group, alkoxy group having 1-4 carbon atoms, carbon represents an alkylthio group having 1-4 carbon atoms or an alkylamino group having 1-4 carbon atoms, and R^1 is phenyl optionally substituted with halogen, alkyl having 1-4 carbon atoms, or haloalkyl having 1-4 carbon atoms; group, a pyridyl group optionally substituted with alkyl having 1 to 4 carbon atoms, or a branched alkyl group having 3 to 6 carbon atoms, and R^2 is substituted with halogen or haloalkyl having 1 to 4 carbon atoms. represents a phenyl group or a branched alkyl group having 3 to 6 carbon atoms, which may be
-6 represents a branched alkyl group, and R^1 and R^2
When simultaneously represents a phenyl group, at least one of the phenyl groups has a substituent. A herbicide containing a 2,4,6-trisubstituted aromatic heterocycle represented by the following as an active ingredient.