JP2002275178A - Pyridylphenyltriazolinone derivative and herbicide - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a new pyridylphenyltriazolinone derivative exhibiting excellent herbicidal activity at a low application rate, excellent selective herbicidal activity between crops and weeds, high safety to crops, man and animals and usable for the treatment of wide variety of objects such as the weeds in paddy field and cropped land and provide a herbicide containing the derivative. SOLUTION: The pyridylphenyltriazolinone derivative is expressed by general formula (I) [R<1> is H, a 1-6C alkyl, a 1-6C halogenated alkyl, a 2-6C alkenyl or a 3-6C alkynyl; R<2> is H or a 1-6C alkyl; R<3> is a halogen atom, a 1-6C alkyl or a halogenated alkyl; R<4> is H or a halogen atom; R<5> is a halogen atom; and R<6> is a halogen atom or a 1-6C halogenated alkyl].

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

TECHNICAL FIELD The present invention relates to a novel pyridylphenyltriazolinone derivative and a herbicide containing the same as a herbicidal active ingredient.

[0002]

BACKGROUND OF THE INVENTION Herbicides are mainly used to control weeds grown on agricultural lands and to create an environment suitable for cultivation of crops. So far, phenoxy, benzoic and phenylacetic acids, halogenated Carboxylic acid, carbamate, urea, acid amide, heterocyclic, phenol,
Herbicides having various structures such as diphenyl ethers and pyridiniums have been proposed or put to practical use.

[0003] Among them, heterocyclic herbicides include:
For example, a phenyltriazolinone derivative may be mentioned, and as a compound belonging to the phenyltriazolinone derivative, compounds described in the following publications are known. (1) JP-A-7-76578 discloses a compound represented by the general formula (A)

[0004]

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In the formula (A), X is an oxygen atom or a sulfur atom, R ¹ is a halogenated alkyl group, R ² is a cycloalkyl group, a cycloalkylalkyl group or the like, and R ³ is a hydrogen atom Or a halogen atom, R ⁴ is a nitrile group or a nitro group, and R ⁵ is a halogen atom, a heterocyclic alkoxy group, or the like. A phenyltriazolinone derivative represented by the formula:
This derivative is described as having herbicidal and acaricidal activity.

(2) US Pat. No. 5,084,085 discloses the general formula (B)

[0007]

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In the general formula (B), X represents a halogen atom, an alkyl group, a halogenated alkyl group or a nitro group, and Y represents a halogen atom, an alkyl group, an alkoxy group, an alkylthio group, a halogenated alkyl group, a nitro group. R ^a is a lower halogenated alkyl group, a lower alkyl group, an alkenyl group or an alkynyl group; R ^b is a hydrogen atom, a halogen atom, a lower alkyl group, a lower halogenated alkyl group, an alkoxy group, R ¹ is a hydrogen atom, an alkyl group, a halogen atom, a halogenated alkyl group, a nitro group, an alkoxy group, an alkylthio group or a cyano group, and R ² is a hydrogen atom, a halogen atom, a hydroxyl group, an alkylcarbonyloxy group, an alkenyloxy group , Cyano group, alkynyloxy group, alkyl group, halogenated alkyl group, alkoxy Group, a haloalkoxy group,
A nitro group, an amino group, an alkylthio group or the like, and Z is an oxygen atom, a sulfur atom, an amino group or an alkylamino group. ], And that the derivative has herbicidal activity.

In general, in developing a herbicide, it is required to develop a herbicide which exhibits a high herbicidal effect even at a low dose, has a wide herbicidal activity against various kinds of weeds, and is excellent in safety. . However, when a phenyltriazolinone derivative as described above is used as the herbicidal active ingredient, the herbicidal effect is insufficient at a low dose, or even when the herbicidal activity is exhibited, selective treatment of crops and weeds is not possible. Since the herbicidal activity is inferior, the phytotoxicity to crops is large, and the herbicide cannot always be used satisfactorily.

[0010]

SUMMARY OF THE INVENTION The object of the present invention is to solve the above problems, exhibit excellent herbicidal activity even at a low dose, and exhibit excellent selective herbicidal activity between crops and weeds. Moreover, it is an object of the present invention to provide a novel pyridylphenyltriazolinone derivative and a herbicide containing the same, which can be used for a wide range of objects such as paddy rice and field crop weeds.

[0011]

SUMMARY OF THE INVENTION The present inventors have conducted intensive studies to solve the above-mentioned problems, and as a result, have found that the compound of the present invention does not cause phytotoxicity to crops, and can be used at low doses on weeds of paddy rice and field crops. The present inventors have found that they show an excellent herbicidal effect and completed the present invention. That is, the pyridylphenyltriazolinone derivative according to the present invention has the general formula (I)

[0012]

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[In the general formula (I), R ¹ represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, a halogenated alkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms or a 3 to 6 carbon atoms.
R ² is a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and R ³ is a halogen atom, an alkyl group having 1 to 6 carbon atoms or a halogenated group having 1 to 6 carbon atoms. R ⁴ is a hydrogen atom or a halogen atom, R ⁵ is a halogen atom, and R ⁶ is a halogen atom or a halogenated alkyl group having 1 to 6 carbon atoms. ].

Further, the herbicide according to the present invention is characterized by containing a pyridylphenyltriazolinone derivative represented by the above general formula (I) as a herbicidal active ingredient. The following general formula (Ia)

[0015]

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[In the general formula (Ia), R ² is a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and R ³ is a halogen atom, an alkyl group having 1 to 6 carbon atoms or a halogen having 1 to 6 carbon atoms. R ⁴ is a hydrogen atom or a halogen atom, R ⁵ is a halogen atom, and R ⁶ is a halogen atom or a halogenated alkyl group having 1 to 6 carbon atoms. ]. A method for producing a pyridylphenyltriazolinone derivative represented by the following general formula (II):
An aniline derivative represented by

[0017]

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[In the general formula (II), R ³ , R ⁴ , R ⁵ , R
⁶ is the same as R ³ , R ⁴ , R ⁵ and R ^{6 in} formula (Ia). Is diazotized with a diazotizing agent, reduced with a reducing agent, and then the resulting hydrazine derivative is converted to a keto acid represented by the following general formula (IV).

[0019]

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[In the general formula (IV), R ² is a group represented by the general formula (I)
Same as R ^{2 in} a). And further reacting the resulting hydrazone derivative with diphenylphosphoryl azide and a base. The method for producing a pyridylphenyltriazolinone derivative represented by the general formula (Ib) comprises reacting a pyridylphenyltriazolinone derivative represented by the general formula (Ia) with a compound represented by the general formula (VI). Features:

[0021]

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[In the general formulas (Ib) and (VI), R
¹ is an alkyl group having 1 to 6 carbon atoms, a halogenated alkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, or an alkynyl group having 3 to 6 carbon atoms. In the general formulas (Ia) and (Ib), R ² is a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and R ³ is a halogen atom, an alkyl group having 1 to 6 carbon atoms or a halogen having 1 to 6 carbon atoms. R ⁴ is a hydrogen atom or a halogen atom, R ⁵ is a halogen atom, and R ⁶ is a halogen atom or a halogenated alkyl group having 1 to 6 carbon atoms. In the general formula (VI), X is a halogen atom. ].

[0023]

DETAILED DESCRIPTION OF THE INVENTION Hereinafter, the pyridylphenyltriazolinone derivative according to the present invention and a herbicide containing the same as a herbicidal active ingredient will be described in detail. Pyridylphenyltriazolinone derivative The pyridylphenyltriazolinone derivative according to the present invention is represented by the following general formula (I).

[0024]

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[0025] [In the general formula (I), R ¹ represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms (lower alkyl), 1 to carbon atoms
6 halogenated alkyl group (a lower alkyl halide group), is any of the alkenyl group having 2 to 6 carbon atoms (lower alkenyl) or alkynyl group having 3 to 6 carbon atoms (lower alkynyl group), R ² is R ³ is a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, R ³ is a halogen atom, an alkyl group having 1 to 6 carbon atoms or a halogenated alkyl group having 1 to 6 carbon atoms, and R ⁴ is a hydrogen atom Or a halogen atom, R ⁵ is a halogen atom, and R ⁶ is a halogen atom or a halogenated alkyl group having 1 to 6 carbon atoms. In the pyridylphenyltriazolinone derivative represented by the general formula (I), the alkyl group contained in R ¹ , R ² , and R ³ is an alkyl group having 1 to 6 carbon atoms, and is a straight-chain alkyl group. Or a branched alkyl group.

The alkyl group having 1 to 6 carbon atoms includes, for example, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, s
-Butyl group, t-butyl group, n-pentyl group, isopentyl group, 2-methylbutyl group, neopentyl group, n-hexyl group, 4-methylpentyl group, 3-methylpentyl group, 2-methylpentyl group, 3, 3-dimethylbutyl group,
1,1-dimethylbutyl group, 1,3-dimethylbutyl group, 2,3
-Dimethylbutyl group, 1-ethylbutyl group, 1-ethyl-2-methyl-propyl group, 1-methyl-1-ethylpropyl group, 1-methyl-2-ethylpropyl group, 2-methyl-1-ethylpropyl group And a 2-methyl-2-ethylpropyl group.

[0027] In the above formula (I), a halogenated alkyl group contained in R ^1, R ^3, R ⁶ is a halogenated alkyl group having the 1 to 6 carbon atoms, the hydrogen atoms in the alkyl group At least a part thereof is substituted with a halogen atom. Examples of the halogen atom include a chlorine atom, a bromine atom, a fluorine atom, and an iodine atom. As such a halogenated alkyl group having 1 to 6 carbon atoms,
For example, a trifluoromethyl group, a chloromethyl group, a bromomethyl group, a dichloromethyl group, a difluoromethyl group, a trifluoromethyl group, a 2-fluoroethyl group,
Chloroethyl group, 2-bromoethyl group, 1,1-difluoroethyl group, 2,2,2-trifluoroethyl group, 3
-Chloropropyl group and 3-iodopropyl group.

During [0028] formula (I), the alkenyl group contained in R ¹ is an alkenyl group of the above 2 to 6 carbon atoms and may be linear or branched. Such carbon number 2-6
Examples of the alkenyl group include a vinyl group, a 1-propenyl group, a 2-propenyl group, a 1-methyl-2-propenyl group, a 2-methyl-2-propenyl group, a 2-ethyl-2-propenyl group, Butenyl group, 1-methyl-2
-Butenyl group, 2-methyl-2-butenyl group, 1-ethyl-2-butenyl group, 3-butenyl group, 2-pentenyl group, 3-pentenyl group, 4-pentenyl group, 2-hexenyl group, 3-hexenyl And 4-hexenyl groups.

In the above formula (I), the alkynyl group contained in R ¹ is an alkynyl group having 3 to 6 carbon atoms, which may be linear or branched. Such carbon number 3-6
Examples of the alkynyl group include a 2-propynyl group, a 1-methyl-2-propynyl group, a 2-butynyl group,
1-methyl-2-butynyl group, 1-ethyl-2-butynyl group, 3-butynyl group, 2-methyl-3-butynyl group,
Examples thereof include a 2-pentynyl group, a 4-pentynyl group, a 2-hexynyl group, a 3-hexynyl group, a 4-hexynyl group, and a 5-hexynyl group.

Examples of the halogen atom include the same as those described above. Tables 1 and 2 show specific examples of the pyridylphenyltriazolinone derivative represented by the general formula (I) according to the present invention. Table 1 below
The compound number in 2 is also referred to in Examples and Test Examples described later.

[0031]

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[0032]

[Table 1]

[0033]

[Table 2]

The pyridylphenyltriazolinone derivative represented by the general formula (I) exhibits a high herbicidal effect even in a small amount, has excellent selective herbicidal activity between crops and weeds, and is safe for crops and humans. Because of its high potency, it is useful as a herbicidal active ingredient. Method for Producing Pyridylphenyltriazolinone Derivative Next, a method for producing the derivative represented by the general formula (I) is represented by the formula
In (I), when R ¹ is a hydrogen atom (method (A)),
The case where R ¹ is any of the other lower alkyl groups, lower halogenated alkyl groups, lower alkenyl groups and lower alkynyl groups (method (B)) will be specifically described.

<Method (A)> R ¹ in the above general formula (I)
Is a hydrogen atom, a pyridylphenyltriazolinone derivative (pyridylphenyltriazolinone derivative (Ia)) represented by the following general formula (Ia), specifically, for example, those as shown in the aforementioned compound Nos. 1 to 30 Can be preferably synthesized by the following three steps.

[0036]

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(The above general formulas (Ia) and (II)
R ^2, R ³ in ^{(V), R 4, R} 5 and R ⁶ are the same as R ^2, R ^3, R ^4, R ⁵ and R ⁶ in the general formula (I). Z is coordinated with an inorganic acid. The method for producing the pyridylphenyltriazolinone derivative (Ia) is briefly described. First, in the first step, an aniline derivative represented by the general formula (II) (aniline derivative (I
I)) is diazotized using a diazotizing agent such as sodium nitrite and then reduced with stannous chloride as a reducing agent to obtain a hydrazine derivative represented by the general formula (III) (hydrazine derivative (III)). Can be

In the second step, the hydrazine derivative (III) obtained in the first step is reacted with a keto acid (keto acid (IV)) represented by the general formula (IV) to obtain a compound represented by the general formula (V). Hydrazone derivative shown (hydrazone derivative (V))
Is obtained. In the third step, the hydrazone derivative (V) obtained in the second step, diphenylphosphoryl azide,
By reacting with a base such as triethylamine, a pyridylphenyltriazolinone derivative (Ia) is obtained.

The above-mentioned first to second steps are usually carried out in one reaction vessel, and are carried out continuously without isolating the hydrazine derivative (III) on the way. Hereinafter, these steps will be described more specifically.

[0040]

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(The above formulas (Ia) and (II))
R ^2, R ³ in ^{(V), R 4, R} 5 and R ⁶ are the same as R ^2, R ^3, R ^4, R ⁵ and R ⁶ in the general formula (I). 1 ) First Step In the first step, a diazonium salt is first produced by reacting an aniline derivative (II) with a diazotizing agent such as sodium nitrite in an aqueous solution of an inorganic acid such as hydrochloric acid.

The diazotizing agent used in the first step includes, for example, isopentyl nitrite in addition to sodium nitrite. In addition, as the inorganic acid used in the first step, in addition to hydrochloric acid, for example, hydrobromic acid,
Sulfuric acid and the like. When the above sodium nitrite is used as the diazotizing agent, it is generally 1.0 to 1.5 mol, preferably 1.0 mol, per 1 mol of the aniline derivative (II).
It is used in an amount of 0 to 1.1 mol, and when hydrochloric acid is used as the inorganic acid, it is used in an amount of 1.1 mol per mol of the aniline derivative (II).
It is used in an amount of 0 to 20.0 mol, preferably 5.0 to 12.0 mol.

The reaction is usually carried out at a temperature of -20 to 20 ° C, preferably -5 to 0 ° C. The reaction time varies depending on the reaction substrate and the reaction temperature, but is usually completed in 10 minutes to 1 hour. Next, an aqueous hydrochloric acid solution of stannous chloride (reducing agent) is added to the aqueous hydrochloric acid solution of the generated diazonium salt to reduce the diazonium salt. As the reducing agent, for example, sodium sulfite may be used instead of stannous chloride. Also, instead of the above hydrochloric acid aqueous solution, hydrobromic acid,
An aqueous solution of an inorganic acid such as sulfuric acid can also be used.

The stannous chloride used as the reducing agent is generally 2.0 mol / mol of the aniline derivative (II).
It is used in an amount of from mol to 4.0 mol, preferably from 2.0 mol to 3.0 mol. When hydrochloric acid is used as the inorganic acid, generally, 2.0 mol to 4.0 mol per 1 mol of stannous chloride,
It is preferably used in an amount of 2.0 mol to 3.0 mol. The reaction is usually performed at a temperature of -30 to 10C, preferably -20 to 0C. The reaction time varies depending on the reaction substrate and the reaction temperature, but is usually completed in 10 minutes to 1 hour.

The hydrazine derivative (III), which is the reaction product of the first step, may be isolated and purified from the reaction solution after the completion of the reaction. 2) used in the second step. Second step In the second step, the reaction solution containing the hydrazine derivative (III) obtained in the first step is mixed with a compound of the formula (IV)
And reacting with the hydrazine derivative (III) in the reaction solution. The keto acid (IV) is used in an amount of 1 to 1 per equivalent of the aniline derivative (II) used in the first step.
It is used in an amount of 1.5 equivalents, preferably 1-1.2 equivalents. The reaction is usually performed at a temperature of 0 to 50 ° C, preferably 0 to 20 ° C. The reaction time depends on the reaction substrate and reaction temperature,
Usually completes in 10 minutes to 2 hours.

The hydrazone derivative (V), which is a reaction product of the second step, precipitates in the form of a powder in the reaction solution after completion of the reaction, and is separated by filtering the powder. The obtained hydrazone derivative (V) may be purified and supplied to the next third step. However, it is usually used without purification, as it is dried as it is to remove water and used in the next step. Can be.

Third Step In the third step, the hydrazone derivative (V) is reacted with diphenylphosphoryl azide and a base such as triethylamine to obtain a pyridylphenyltriazolinone derivative (Ia). In this reaction, a solvent can be used. Examples of the solvent used include benzene,
Examples thereof include aromatic hydrocarbons such as toluene and xylene, and toluene is preferably used. Two or more such solvents may be used in combination. Such a solvent is used in an appropriate amount.

As the base, in addition to triethylamine, for example, tributylamine, diethylisopropylamine and the like can be used. The diphenylphosphoryl azide and triethylamine used are used in an amount of 1.0 to 1.1 mol (10 mol / mol) relative to 1 mol of the hydrazone derivative (V).
% Excess), but preferably used in equimolar amounts. The reaction is usually performed at 80 to 150 ° C, preferably 100 to 12 ° C.
Performed at a temperature of 0 ° C. The reaction time varies depending on the reaction substrate and the reaction temperature, but is usually completed in 30 minutes to 3 hours.

The reaction solution thus obtained contains the pyridylphenyltriazolinone derivative (Ia) of the present invention.
The derivative (Ia) is separated from the reaction solution by a usual post-treatment (purification). Post-treatment (purification) The method of post-treatment will be specifically described.

The reaction solution obtained in the third step is extracted with an alkali by adding, for example, a 2N aqueous sodium hydroxide solution, and the alkali extract is neutralized with concentrated hydrochloric acid.
The pyridylphenyltriazolinone derivative (Ia) is precipitated as a powder or as an oil. When the pyridylphenyltriazolinone derivative (Ia) precipitates as a powder, it can be isolated by filtration. When precipitated as an oil, it can be extracted and isolated using an extraction solvent such as toluene or ethyl acetate.

The thus obtained pyridylphenyltriazolinone derivative (Ia) can be further purified, if necessary, by an operation such as column chromatography or recrystallization. <Method (B)> When R ¹ in the general formula (I) is a group other than a hydrogen atom, that is, when R ¹ is a group having 1 to 6 carbon atoms.
An alkyl group, a halogenated alkyl group having 1 to 6 carbon atoms,
A pyridylphenyltriazolinone derivative (pyridylphenyltriazolinone derivative (Ib)) represented by the following formula (Ib), which is an alkenyl group having 2 to 6 carbon atoms or an alkynyl group having 3 to 6 carbon atoms, specifically Is compound No.3
The compounds shown in 1 to 85 can be preferably synthesized by the following synthetic route (reaction (B)).

[0052]

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[0053] [the above general formula (Ia) and R ² in ^{(Ib), R 3, R} 4, R 5 and R ^6, R ^2, R ³ in the general formula (I), R ^4, R ⁵ and is similar to R ^6. R ¹ in the general formula (VI) and (Ib), except that it does not include the hydrogen atom is the same as R ¹ in general formula (I), X
Is a halogen atom such as a chlorine atom, a bromine atom and an iodine atom. That is, the pyridylphenyltriazolinone derivative (Ib) is a pyridylphenyltriazolinone derivative (Ia) and a compound represented by the general formula (VI)
(Method (B) or reaction (B)).
Also called).

Hereinafter, the reaction (B) will be described more specifically. The reaction (B) is usually carried out in the presence of a solvent,
The reaction is performed by mixing the pyridylphenyltriazolinone derivative (Ia) obtained by the above method (A), the halides (VI), and the dehydrohalogenating agent. If these halides (VI) are liquid or solid, they may be used in an equimolar amount with respect to 1 mol of the pyridylphenyltriazolinone derivative (Ia). , Preferably in an amount of 1.0 to 1.2 mol. Also,
When the halide (VI) is a gas (gas), it is used in an excess amount or an appropriate amount.

The dehydrohalogenating agent used in the reaction (B) has a function of accelerating the reaction of (Ia) → (Ib), and a base is used as such a dehalogenating agent. Such bases include, for example, organic tertiary amines such as triethylamine, tributylamine, diethylisopropylamine, 4-dimethylaminopyridine and pyridine; and alkalis such as sodium methoxide, sodium ethoxide and potassium tert-butoxide. Metal alkoxides, sodium carbonate, alkali metal carbonates such as potassium carbonate, sodium hydroxide, alkali metal hydroxides such as potassium hydroxide, sodium hydride, alkali metal hydrides such as potassium hydride Among them, potassium carbonate is preferable.

When potassium carbonate is used as the base, the pyridylphenyltriazolinone derivative (Ia)
It is desirable to use 1.0 to 1.5 mol, preferably 1.0 to 1.2 mol, per 1 mol. Examples of the reaction solvent used in the reaction (B) include aromatic hydrocarbons such as benzene, toluene and xylene; aliphatic alcohols such as methyl alcohol, ethyl alcohol and tertiary butyl alcohol; acetonitrile and propionitrile Such as nitriles, esters such as ethyl acetate and ethyl propionate, ethers such as diethyl ether and tetrahydrofuran, ketones such as acetone and methyl ethyl ketone, N, N-dimethylformamide, N, N-dimethylacetamide And pyridine and the like can be used. Such a solvent can also be used as a mixed solvent obtained by combining two or more kinds. Of these, acetonitrile and N, N-dimethylformamide are preferred.

The reaction (B) is usually carried out at room temperature (eg, 20
C) to 150C, preferably from 20 to 80C. The reaction time depends on the reaction temperature and the reaction substrate,
Usually completes in 30 minutes to 24 hours. Pyridylphenyltriazolinone derivative (Ib) which is a reaction product of the above reaction
Can be obtained, for example, by adding an extraction solvent such as toluene or ethyl acetate and water to the reaction solution containing the derivative (Ib), washing with water, and distilling off the solvent. The obtained target product (pyridylphenyltriazolinone derivative (I
If necessary, b)) can be further purified by an operation such as column chromatography or recrystallization.

Examples of the production of the compound (I) of the present invention obtained by the above two methods (A) and (B) are shown in Examples 1 to 3 below. The aniline derivative (II), which is a starting material used in the first step of the above method (A), is
For example, it can be synthesized according to the method described in Japanese Patent Publication No. 9-503747. The production is shown in Reference Production Examples described later. Further, the keto acid (IV) used in the second step of the above method (A) and the halides (VI) used in the above method (B) are known ones and are commercially available as reagents.

Next, the herbicide according to the present invention will be described in detail. The herbicide according to the present invention contains a pyridylphenyltriazolinone derivative represented by the above general formula (I) as a herbicidal active ingredient. The pyridylphenyltriazolinone derivative (I) of the present invention has excellent herbicidal activity as shown in the test examples described later, and also has excellent selective killing between the following weeds and crops. Since it shows herbal activity, it can be used as a herbicidal active ingredient of a herbicide for controlling weeds or a selective herbicide.

Accordingly, a herbicide containing the pyridylphenyltriazolinone derivative (I) having such properties as an active ingredient for herbicide exhibits excellent herbicidal effects,
Since the herbicidal selectivity between weeds and crops is excellent, the use of the herbicide of the present invention provides a safe and high-quality crop. The herbicide of the present invention is effective for, for example, grasses and broadleaf weeds.

Examples of the weeds of the family Gramineae include, for example, Alopecurus, Oven (Avena), Barley (Bromus), Cyperus (Cyperus), and Mehishiba (Dig).
itaria), barnyard millet (Echinochloa) and kuroguwai (Eleocha)
ris), Ohishiba (Eleusine), and Eel (Monochori)
a), giant cane (Panicum), and pomegranate (Paspal)
um), Giant Woodpecker (Phleum), Sparrow Poa (Poa), Omodaka (Sagittaria), Firefly (Scirpu)
s), Enokorogosa (Setaria), Johnsongrass (Sor
ghum).

As broadleaf weeds, for example, strawberry (Abu
tilon), Amaranthus, Ragweed (Ambrosi)
a), Butters (Bidens), Akaza (Chenopodiu)
m), Yaemura (Galium), Convolvulus (Ipomoea), Azena
(Lindernia), Porcupine (Persicaria), Purslane (Por
tulaca), stag beetle (Rotala), chickweed (Stellari)
a), violets (Viola), and red fir (Xanthium).

Examples of crops (useful cultivated plants) of grasses in a field to which the herbicide of the present invention can be applied include, for example,
Barley (Hordeum), Rice (Oryza), Sugarcane (Sa)
ccharum), wheat (Triticum), corn (Zea)
And the like. Examples of broadleaf crops to which the herbicide of the present invention can be applied include peanuts (Arachis), sugar beets (Beta), rape (Brassica), and soybeans (Glycin).
e), cotton (Gossypium), tomato (Lycopersicon) and the like.

The pyridylphenyltriazolinone derivative (I) of the present invention exhibits excellent selective herbicidal activity between the weeds and crops as described above, and therefore contains the derivative (I) as a herbicidal active ingredient. Herbicides are effective as selective herbicides between the weeds and crops. It goes without saying that the application of the herbicide of the present invention is not limited to the weeds and crops exemplified above.

The herbicide of the present invention can be used in various dosage forms, and when it is formulated, its active ingredient, that is, the pyridylphenyltriazolinone derivative (I), which is the herbicidal active ingredient, is added to a carrier or diluent. If necessary, a method such as mixing with at least one of additives (eg, surfactants) and auxiliary agents by a known method can be adopted, and the herbicide thus obtained is usually used. It can be used in the form of formulations used as agricultural chemicals, for example, granules, fine granules, wettable powders, wettable powders, emulsions, aqueous solvents, flowables, tablets, powders, microcapsules, pastes and the like.

The herbicide of the present invention may also contain other pesticides such as fungicides, insecticides, herbicides, acaricides, and safeners.
(Sifner), a plant growth regulator, a fertilizer, a soil conditioner, or the like, and may be used as a mixture or in combination. In particular, by mixing and using other pesticides, the amount of herbicide used can be reduced, and labor saving can be achieved.
In addition, the herbicide application target (herbicide spectrum) can be expanded by the cooperative action of the two drugs, and further, a stronger effect can be expected from the synergistic action of the two drugs. At this time, a plurality of known herbicides and safeners (safeners) can be simultaneously combined and blended.

In the preparation of the preparation, any solid or liquid carrier can be used as long as it is generally used for agricultural chemicals. Such carriers are not limited to specific ones, but specific examples include the following. Examples of solid carriers include mineral powders (kaolin, bentonite, clay, montmorillonite, talc, diatomaceous earth, mica, vermiculite, quartz, calcium carbonate, apatite, white carbon, slaked lime, silica sand, ammonium sulfate, urea, etc.) Powders (soy flour, wheat flour, wood flour, tobacco flour, starch, crystalline cellulose, etc.), polymer compounds (petroleum resin, polyvinyl chloride, ketone resin, etc.), alumina, silicates, sugar polymers, highly dispersible Examples include silicic acid and waxes.

Examples of the liquid carrier include water, alcohols (methyl alcohol, ethyl alcohol, n-propyl alcohol, isopropyl alcohol, butanol, ethylene glycol, benzyl alcohol, etc.),
Aromatic hydrocarbons (toluene, benzene, xylene, ethylbenzene, methylnaphthalene, etc.), ethers (ethyl ether, ethylene oxide, dioxane, tetrahydrofuran, etc.), ketones (acetone, methyl ethyl ketone, cyclohexanone, methyl isobutyl ketone, isophorone, etc.), Esters (ethyl acetate, butyl acetate, ethylene glycol acetate, amyl acetate, etc.), acid amides (dimethylformamide, dimethylacetamide, etc.), nitriles (acetonitrile, propionitrile, acrylonitrile, etc.), sulfoxides (dimethylsulfoxide, etc.) , Alcohol ethers (ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, etc.), aliphatic or alicyclic hydrocarbons (n-hexane, Etc. Rohekisan), industrial gasoline (petroleum ether, solvent naphtha, etc.), petroleum fractions (paraffins, kerosene, etc. gas oil) and the like.

When the herbicide is formulated into an emulsion, a wettable powder, a flowable or the like, emulsification, dispersion, solubilization,
Various surfactants are blended for the purpose of wetting, foaming, lubrication, spreading and the like. Examples of such surfactants include nonionic surfactants such as polyoxyethylene alkyl ether, polyoxyethylene alkyl ester, and polyoxyethylene sorbitan alkyl ester;
Anionic surfactants such as alkyl benzene sulfonate, alkyl sulfosuccinate, alkyl sulfate, polyoxyethylene alkyl alkyl sulfate, aryl sulfonate, alkylamines (laurylamine, stearyltrimethylammonium chloride, etc.), polyoxyethylene alkylamines, etc. Amphoteric surfactants such as a cationic surfactant, a carboxylic acid (betaine type), and a sulfate salt, but are not limited to these examples.

Other than these, polyvinyl alcohol (PVA), carboxymethyl cellulose (CMC), gum arabic, polyvinyl acetate, sodium alginate,
Various auxiliaries and additives such as gelatin and tragacanth rubber can be used. The herbicide of the present invention desirably contains the pyridylphenyltriazolinone derivative (I) in the range of 0.001 to 95% by weight, preferably 0.01 to 75% by weight, regardless of the dosage form. More specifically,
Generally, when the herbicide is a granule, the derivative (I) is
When the herbicide is a wettable powder, a flowable, a dry flowable, a liquid or an emulsion, the derivative (I) is used in an amount of 1 to 75% by weight, and ,
When the herbicide of the present invention is a powder, a driftless powder or a fine powder, the derivative (I) can be contained in an amount of 0.01 to 5% by weight.

The herbicide thus prepared is, for example, in the case of granules and flowables, as it is, on a soil surface, in soil or in water, as an active ingredient in a converted amount of 10%.
It may be applied in an amount of about 0.3 g to 300 g per are. In the case of wettable powders, emulsions, and the like, the diluted chemical solution obtained by diluting with water or a suitable solvent may be sprayed in the range of about 0.3 g to 300 g per 10 ares as the effective ingredient.

[0072]

Industrial Applicability The pyridylphenyltriazolinone derivative (I) of the present invention exhibits excellent herbicidal activity at a low dose, has excellent selective herbicidal activity between crops and weeds, and is safe for crops and humans. And it can be used as a novel herbicidal active ingredient which can be used for a wide range of subjects such as paddy rice and field crop weeds.

According to the herbicide of the present invention containing the pyridylphenyltriazolinone derivative (I), an excellent herbicidal effect can be obtained at a low dose on rice and field crop weeds without causing phytotoxicity to the crop. Therefore, high quality crops with high safety can be obtained.

[0074]

EXAMPLES Hereinafter, the present invention will be described specifically with reference to Examples, but the present invention is not limited to these Examples. In the following Production Examples, Examples, and Test Examples, the term "room temperature" refers to about room temperature unless otherwise specified.
Indicates 20 ° C.

The structures of the compounds in the following examples were determined by mass spectrometry (QP1100EX mass spectrometer manufactured by Shimadzu Corporation).

[0076]

[Reference Production Example] <4-Fluoro-2-chloro-5- (3
-Chloro-5-trifluoromethyl-pyridin-2-yl) -aniline [in the above general formula (II), R ³ is a chlorine atom,
R ⁴ is a fluorine atom, the production of R ⁵ compound chlorine atom and R ⁶ is a trifluoromethyl group]>

[0077]

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1) 2- (4-chloro-2-fluorophene)
Nyl) -3-chloro-5-trifluoromethylpyridine
Under a nitrogen stream, 2,3-dichloro-5-trifluoromethylpyridine 2 was placed in a 500 ml four-necked flask equipped with a production stirrer, a reflux condenser and a thermometer capable of measuring up to 100 ° C.
1.6 g (0.1 mol), dichloro [1,3-bis (diphenylphosphino) propane] palladium (II) and 120 ml of tetrahydrofuran were added, and the mixture was heated under reflux. To this solution,
25.1 g of fluoro-4-chloro-bromobenzene (0.12mo
l), 2-fluoro-4-chlorophenylmagnesium bromide prepared from 3.7 g (0.15 mol) of magnesium and 100 ml of tetrahydrofuran were added dropwise over 60 minutes, and the mixture was further stirred under reflux for 1 hour. After cooling the obtained reaction mixture, it was poured into 200 ml of ice water, and acidified by adding 1N hydrochloric acid.
The mixture was transferred to a separating funnel having a capacity of 1000 ml and extracted by adding 300 ml of toluene. The organic layer is further washed with water and dried over anhydrous sodium sulfate.
After drying with 50 g, the sodium sulfate used for the drying was separated by filtration using a Nutsche type 6 cm diameter Kiriyama funnel (trade name) under reduced pressure using an aspirator. The filtrate was concentrated under reduced pressure using an aspirator. The obtained residue is mixed with a hexane-toluene mixture (solvent volume ratio: hexane:
Purification by silica gel chromatography using silica gel (manufactured by Merck, trade name: silica gel 60H) using toluene = 4: 1) to give the title compound 2-
(4-Chloro-2-fluorophenyl) -3-chloro-5-
25.1 g of trifluoromethylpyridine was obtained (81% yield,
Oil).

2) 2- (4-Chloro-2-fluoro-5-
Nitrophenyl) -3-chloro-5-trifluoromethyl
Preparation of pyridine In a 300 ml four-necked flask equipped with a stirrer, a reflux condenser and a thermometer capable of measuring up to 100 ° C., 2- (4-chloro-2-fluorophenyl) -3-chloro-5-trifluoro was added. 18.6 g (0.06 mol) of methylpyridine and 100 m of concentrated sulfuric acid
l was added and dissolved. To this solution, 3% under ice water cooling, 69%
A mixed acid consisting of 6 g of nitric acid and 10 ml of concentrated sulfuric acid was added dropwise over 60 minutes, and the mixture was further stirred at room temperature for 2 hours. The obtained reaction mixture solution was slowly poured into 300 g of ice, transferred to a 1000-ml separating funnel, and extracted by adding 300 ml of toluene. 2 toluene layers
It was washed once with water, washed with a 1N sodium hydroxide solution, further washed with water, and dried with 50 g of anhydrous sodium sulfate. The sodium sulfate used for this drying was filtered using a Nutsche-type 6 cm diameter Kiriyama funnel (trade name) under reduced pressure using an aspirator. The filtrate was concentrated under reduced pressure using an aspirator. The obtained residue was purified by silica gel chromatography using silica gel (manufactured by Merck, trade name: silica gel 60H) using toluene as a developing solvent to give 2- (4-chloro-2) as the title compound. 19.6 g of (-fluoro-5-nitrophenyl) -3-chloro-5-trifluoromethylpyridine was obtained (92% yield, oil).

3) 4-Fluoro-2-chloro-5-
(3-chloro-5-trifluoromethyl-pyridine-2
-Il) aniline production 8.4 g of reduced iron in a 300 ml four-necked flask equipped with a stirrer, reflux condenser and thermometer capable of measuring up to 100 ° C.
(0.15 mol), 80 ml of methyl alcohol and 40 ml of acetic acid, and the mixture was heated under reflux. The suspension is treated at 60 ° C. with 2- (4-chloro-2-fluoro-5-nitrophenyl) -3-chloro-5.
A solution of 17.7 g (0.05 mol) of trifluoromethylpyridine dissolved in 20 ml of methyl alcohol was added dropwise over 50 minutes. The mixture was further stirred at 70 ° C. for 2 hours. After cooling the resulting reaction mixture, it was transferred to a 500 ml eggplant-shaped flask, methyl alcohol was distilled off under reduced pressure, 200 ml of ice water was added, and the mixture was extracted with 250 ml of ethyl acetate. The solution was transferred to a separatory funnel having a capacity of 1000 ml, and the layers were separated. The ethyl acetate layer was washed with water, washed with a 1N sodium hydroxide solution, further washed with water, and dried with 50 g of anhydrous sodium sulfate. The sodium sulfate used for this drying was filtered under a reduced pressure by an aspirator using a Nutsche type 6 cm diameter Kiriyama funnel (trade name). The filtrate was concentrated under reduced pressure using an aspirator. The obtained residue was purified by silica gel chromatography using silica gel (manufactured by Merck, trade name: silica gel 60H) using toluene as a developing solvent to give 4-fluoro-2-chloro-5, the target compound of the title. -(3-chloro-5-
Trifluoromethyl-pyridin-2-yl) aniline 1
5.4 g were obtained (95% yield, mp 88-90 ° C.).

[Pyridylphenyltriazolinone Derivative (I)] Examples 1 to 3 show production examples of the pyridylphenyltriazolinone derivative (I) of the present invention.

[0082]

Example 1 <2- [4-Fluoro-2-chloro-5-
(3-chloro-5-trifluoromethyl-pyridine-2
Preparation of -yl) phenyl] -5-methyl-1,2,4-triazol-3-one (compound No. 27 in Table 1) [by method (A)]> stirrer, reflux condenser and-
In a 1000 ml four-necked flask equipped with a thermometer capable of measuring from 100 to 50 ° C, 4-fluoro-2-chloro-5-
(3-chloro-5-trifluoromethyl-pyridine-2
-Yl) aniline (32.5 g, 0.1 mol) and 15% hydrochloric acid (250 ml) were added, followed by vigorous stirring for 30 minutes. To the reaction solution, 7.6 g (0.11 mol) of sodium nitrite dissolved in 40 ml of water was added dropwise at −3 ° C. over 70 minutes while cooling with an ice salt bath, followed by stirring at 0 ° C. for 30 minutes.

Then, the reaction mixture was prepared in a 2000 ml four-necked flask equipped with a stirrer, a reflux condenser and a thermometer capable of measuring from -100 to 50 ° C. separately. Into a water solution of 67.7 g (0.3 mol) of the product in 180 ml of 20% hydrochloric acid, under dry ice-acetone bath cooling-
Added at 20 ° C. After the addition, the dry ice-acetone bath was removed, and the mixture was further stirred for 1 hour. Meanwhile, the reaction temperature became room temperature.

Thereafter, 400 ml of water was added to the obtained reaction mixture, and 9.7 g (0.11 mol) of pyruvic acid was added dropwise thereto at room temperature, followed by vigorous stirring for 2 hours. The precipitated crystals [4-fluoro-2-chloro-5- (3-chloro-5-trifluoromethyl-pyridin-2-yl) phenylhydrazonopropionic acid] are filtered using a Nutsche filter under reduced pressure using an aspirator. The residue was washed with water and further washed with hexane. Thereafter, the product was sufficiently dried to obtain 32 g of a crude product.

32 g of the crude product was weighed in 1000 ml equipped with a stirrer, a reflux condenser and a thermometer capable of measuring up to 200 ° C.
Was placed in 300 ml of toluene in a four-necked flask. To this mixture, 7.9 g (0.078 mol) of triethylamine and 21.5 g (0.078 mol) of diphenylphosphoryl azide were added, and the mixture was heated to reflux slowly so that the temperature gradually increased. After heating and refluxing for 2 hours, allow to cool sufficiently, and 200 ml of an 8% aqueous sodium hydroxide solution.
Extracted. When the alkali extraction solution was acidified (pH 2) with 18% hydrochloric acid under ice water cooling, an oily substance precipitated. The oil was extracted with 300 ml of ethyl acetate, transferred to a separatory funnel having a capacity of 1000 ml, and separated. The ethyl acetate layer was further washed with water and dried with 50 g of anhydrous sodium sulfate. The sodium sulfate used for this drying was Nutsche type 6c under reduced pressure using an aspirator.
Filtration was performed using a Kiriyama funnel (trade name) having a diameter of m. The filtrate was concentrated under reduced pressure using an aspirator. The obtained residue was purified by silica gel chromatography using silica gel (manufactured by Merck, trade name: silica gel 60H) using a toluene-acetone mixture (solvent volume ratio: toluene: acetone = 20: 1) as a developing solvent, 2- [4-Fluoro-2-chloro-5- (3-chloro-5-trifluoromethyl-pyridin-2-yl) phenyl] -5-methyl-1,2,4-triazole as the title compound -3-
21.6 g were obtained (68% yield, melting point: 190-192 ° C, MS (70%).
eV): m / e = 406 (M ⁺ ), 371,322,287).

[0086]

Example 2 <2- [4-Fluoro-2-chloro-5-
(3-chloro-5-trifluoromethyl-pyridine-2
-Yl) phenyl] -4,5-dimethyl-1,2,4-
Preparation of Triazol-3-one (Compound No. 42 in Table 1) [According to Method (B)]> In a 100 ml four-necked flask equipped with a stirrer, a reflux condenser and a thermometer capable of measuring up to 100 ° C. -[4-fluoro-2-chloro-5-
(3-chloro-5-trifluoromethyl-pyridine-2
-Yl) phenyl] -5-methyl-1,2,4-triazol-3-one (4.1 g, 10 mmol) was dissolved in acetonitrile (40 ml), and potassium carbonate (1.7 g, 12 mmol) was added.
Stir vigorously for minutes. 1.7 g (12 mmol) of methyl iodide dissolved in 5 ml of acetonitrile was added dropwise to the thus obtained mixture, and the mixture was stirred at 40 ° C. for 2 hours. The resulting reaction mixture was filtered using a Nutsche type 4 cm diameter Kiriyama funnel (trade name) to remove insolubles under reduced pressure using an aspirator, and the filtrate was concentrated under reduced pressure using an aspirator. The resulting residue was purified by silica gel chromatography (manufactured by Merck, trade name: Silica Gel 60H) using a toluene-acetone mixture (solvent volume ratio: toluene: acetone = 20: 1) as a developing solvent, and the title compound 3.9 was obtained. g (93%, melting point: 173-175 ° C., MS (70 eV): m / e = 420).
(M ⁺ ), 385,322,287).

[0087]

Example 3 <2- [4-Fluoro-2-chloro-5-
(3-chloro-5-trifluoromethyl-pyridine-2
-Yl) phenyl] -4-difluoromethyl-5-methyl-1,2,4-triazol-3-one (Compound No. 71 in Table 1) [by method (B)]> Stirrer, reflux cooling In a 100 ml four-necked flask equipped with a thermometer and a thermometer capable of measuring up to 100 ° C., 2- [4-fluoro-
2-chloro-5- (3-chloro-5-trifluoromethyl-pyridin-2-yl) phenyl] -5-methyl-
4.1 g (10 mmol) of 1,2,4-triazol-3-one was dissolved in 50 ml of acetonitrile, and 2.0 g (15 mmol) of potassium carbonate was dissolved.
Was added and stirred vigorously at room temperature for 30 minutes. Chlorodifluoromethane gas was introduced into the thus obtained mixture while heating at 60 ° C. for 4 hours. The obtained reaction mixture was filtered using a Nutsche type 4 cm diameter Kiriyama funnel (trade name) under reduced pressure using an aspirator to remove insolubles, and the filtrate was concentrated under reduced pressure using an aspirator. The resulting residue was purified by silica gel chromatography (manufactured by Merck, trade name: silica gel 60H) using chloroform as a developing solvent to obtain 2.8 g of the title compound (yield 62%, melting point: 111 to 113). ° C, MS (70 eV): m / e = 456 (M ⁺ ), 406,371,3
22,287).

[Preparation of Herbicide] The method of formulating the pyridylphenyltriazolinone derivative (I) of the present invention as a herbicide will be specifically described with reference to Examples 4 to 9 below. However, it is needless to say that the herbicide of the present invention is not limited to these Examples 4 to 9, but can be mixed with other various additives at an arbitrary ratio to prepare a formulation.

The compound numbers are those shown in Tables 1 and 2 above, and in the following examples, "parts" are all parts by weight.

[0090]

Example 4 (Granules) 1 part of the compound of No. 71, 1 part of calcium ligninsulfonate, 1 part of lauryl sulfate, 30 parts of bentonite and 67 parts of talc were mixed with 15 parts of water and kneaded with a kneader. And granulated with an extrusion granulator. This was dried with a fluidized drier to obtain granules containing 1% of a herbicidal active ingredient (Compound No. 71).

[0091]

Example 5 (Flowable agent) 20.0 parts of No. 42 compound,
2.0 parts of sodium sulfosuccinate di-2-ethylhexyl ester, 2.0 parts of polyoxyethylene nonyl phenyl ether, 5.0 parts of propylene glycol, 0.5 part of an antifoaming agent and 70.5 parts of water are uniformly mixed and pulverized with a wet ball mill, and herbicidally active ingredients. A flowable containing 20% of (Compound No. 42) was obtained.

[0092]

Example 6 (Dry flowable agent) No. 65 compound 75
Part, Isoban No.1 [Anionic surfactant: Kuraray Isoprene Chemical Co., Ltd., trade name] 10 parts, Vanirex N
[Anionic surfactant: Sanyo Kokusaku Pulp Co., Ltd., trade name] 5 parts, 5 parts of white carbon and 5 parts of clay are uniformly mixed and pulverized, and the herbicidal active ingredient (compound No. 65) 75%
A dry flowable (hydration of granules) preparation was obtained.

[0093]

Example 7 (Wettable powder) 15 parts of No. 27 compound, 15 parts of white carbon, 3 parts of calcium ligninsulfonate, 2 parts of polyoxyethylene nonylphenyl ether, 5 parts of diatomaceous earth
Parts and 60 parts of clay are uniformly mixed with a grinder to obtain a wettable powder containing 15% of a herbicidally active ingredient (Compound No. 27).

[0094]

Example 8 (Emulsion) 20 parts of Compound No. 68, Solpol 7
00H [Emulsifier: trade name of Toho Chemical Co., Ltd.] 20 parts and xylene 60 parts were mixed, and a herbicidal active ingredient (Compound No. 6) was mixed.
8) An emulsion containing 20% was obtained.

[0095]

Example 9 (Powder) No. 38 compound 0.5 part, white carbon 0.5 part, calcium stearate 0.5 part, clay 5
0.0 parts and 48.5 parts of talc were uniformly mixed and pulverized to obtain a powder containing 0.5% of a herbicidally active ingredient (Compound No. 38).

The pyridylphenyltriazolinone derivative (I) represented by the general formula (I) can be prepared in various dosage forms according to the preparation examples shown in Examples 4 to 9 described above. . [Herbicidal Effect Test / Pharmaceutical Test] Next, Test Examples 1 and 2 will be shown to exemplify the herbicidal effect of the pyridylphenyltriazolinone derivative (I) of the present invention.

[0097]

[Test Example 1] Herbicidal effect test and transplantation on paddy field weeds
Paddy rice phytotoxicity test Fill a paddy field soil into a 1 / 5,000 arel-sized Wagner pot, add water, mix with fertilizer (N: P: K = 17: 17: 17),
I did a puddling. After that, 30 seeds of each of the seeds of the foxtail, broadleaf weeds (Azena, Konagi, Kikasigusa) and firefly were sown at a depth of 1 to 2 cm. Immersed immediately after sowing, the water depth was maintained at about 2 cm. Subsequent management was performed in a glass greenhouse. Two days after sowing, the two-leaf rice is transplanted,
One day after rice transplantation, the wettable powder prepared according to Example 7 was diluted with water using the compounds shown in Table 4 below, and a predetermined amount of the diluted water solution was dropped.

This test was carried out twice in one chemical concentration section. Twenty-one days after the chemical treatment, the herbicidal rate (%) was obtained by the following formula, and the herbicidal effect and the phytotoxicity were investigated based on the following evaluation indexes. .

[0099]

(Equation 1)

[0100]

[Table 3]

The results are shown in Table 4 below. The compound numbers in Table 4 are the same as those shown in Table 1 above. As a comparative drug, a wettable powder containing Comparative Compound C represented by the following formula was prepared according to Example 7, and a test was conducted in the same manner. Table 4 shows the results. Comparative compound C used as a comparative drug is a compound represented by the following formula (C) (described in US Pat. No. 5,084,085).

[0102]

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[0103]

[Table 4]

[0104]

[Test Example 2] Herbicidal effect test and phytotoxicity on upland weeds
Test 1) Herbicidal effect test on upland weeds Fill the field soil (alluvial loam) in a 1/5000 areal pottery pot, fill the soil with a surface of 1cm and the crabgrass, enokorogusa,
Fifty seeds of each of the weed seeds, i.e., ibis, and o., Were uniformly mixed, and the surface layer was lightly pressed. Two days after sowing,
Emulsions prepared according to Example 8 were diluted with water using the compounds shown in Table 5 below, and the diluted water solution was sprayed on the soil surface at a rate of 100 liters per 10 ares. When the application rate of the active ingredient was converted, it was equivalent to 30 g per 10 ares.
30 days after the chemical treatment, the herbicidal effect was evaluated according to the same criteria as in Test Example 1. Table 5 shows the results.

2) Chemical Injury Test on Crops Field soil (alluvial loam) was filled in a 1 / 10,000 ares-size unglazed pot, and seeds (5 soybeans, corn 5
Seeds, 10 sugar beets, 10 rapeseed, 5 cotton, 10 wheat and 10 barley) in different pots,
The surface layer was lightly pressed. One day after sowing, the emulsion prepared according to Example 8 was diluted with water using the compounds shown in Table 5 below, and the diluted water solution was sprayed onto the soil surface at a rate of 100 liters per 10 ares. When the application rate of the active ingredient was converted, it corresponded to 30 g per 10 ares. Thirty days after the chemical treatment, the degree of phytotoxicity on each crop was investigated based on the same criteria as in Test Example 1.

Table 5 shows the results. In Table 5 below, the compound numbers are the same as those shown in Table 1 above. In each of the tests 1) and 2), a test was carried out in the same manner using the emulsion prepared according to Example 8 except that the comparative drug C of Test Example 1 was used. Table 5 shows the results.

[0107]

[Table 5]

 ────────────────────────────────────────────────── ─── Continuing on the front page (72) Inventor Mitsuyasu Okamura 1-1432 Ishida, Isehara-shi, Kanagawa 101 High Mussoleil 101 (72) Takashi Takeuchi 2-3396, Iriya, Zama-shi, Kanagawa 2 Green Village B −101 F term (reference) 4C063 AA01 BB06 CC41 DD12 EE03 4H011 AB01 AB02 BA01 BA05 BB09 BC01 BC07 BC18 BC19 BC20 DA02 DA15 DA16 DC04 DC05 DC06 DC08 DD01 DD04 DH03

Claims (2)

[Claims] 1. A compound of the general formula (I) [In the general formula (I), R ¹ is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, a halogenated alkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms or alkynyl having 3 to 6 carbon atoms. R ² is a hydrogen atom or a group having 1 carbon atom
R ³ is a halogen atom, an alkyl group having 1 to 6 carbon atoms or a halogenated alkyl group having 1 to 6 carbon atoms, R ⁴ is a hydrogen atom or a halogen atom, R ⁵ is a halogen atom, and R ⁶ is a halogen atom or a halogenated alkyl group having 1 to 6 carbon atoms. A pyridylphenyltriazolinone derivative represented by the formula: 2. A herbicide comprising the pyridylphenyltriazolinone derivative represented by the general formula (I) according to claim 1 as a herbicidal active ingredient.