JPH07215970A - Indazolesulfonylurea derivative, use thereof and intermediate for producing the same - Google Patents

Abstract

PURPOSE:To provide an indazolesulfonylurea derivative having excellent herbicidal effects against weeds in paddy fields and upland fields, excellent in safety for crops, and useful as a herbicide for the paddy fields, upland fields, etc. CONSTITUTION:A compound of formula I [R<1> is H, (cyclo)alkyl, alkoxyalkyl, benzyl(oxoalkyl), etc.; R<2>, R<3> are H, halogen, (cyclo)alkyl, (alkoxycarbonyl) alkenyl, alkynyl, etc.; A, B are (halo)alkyl, monoalkylamino, dialkylamino, halogen, etc.; Z is methine, N; X is O, S; Y is H, (alkoxy)alkyl] or a compound of formula II. For exarfmple, 1-(1-methyl-4-fluoro-1H-indazole-3-sulfonyl)-3-(4,6- dimethoxypyrimidin-2-yl)urea. The compound of formula I is obtained e.g. by reacting a compound of formula III with a compound of formula IV.

Description

Detailed Description of the Invention

[0001]

FIELD OF THE INVENTION The present invention relates to a novel indazolesulfonylurea derivative (hereinafter referred to as "invention compound"), a production intermediate thereof and a herbicide containing the same as an active ingredient.

[0002]

2. Description of the Related Art Up to now, many sulfonylurea derivatives such as sulfometuron methyl have been known as herbicides. The specification of JP-A-4-95091 describes a herbicide containing indazole sulfonylurea as an active ingredient. However, a sulfonylurea derivative in which the sulfamoyl group is substituted at the 3-position of the indazole ring of the compound of the present invention is not known. Furthermore, the indazole sulfonamide derivative which is a production intermediate thereof is not known.

[0003]

It is known that sulfonylurea derivatives have herbicidal activity, but it is difficult to say that these compounds have insufficient herbicidal efficacy or are practically satisfactory.

[0004]

Means for Solving the Problems In view of the above situation, the present inventors have conducted various investigations, and as a result, found that the compound of the present invention is an excellent herbicide having high activity, and completed the present invention. Came to.

That is, the present invention is of the formula [I] or [II]

[0006]

[Chemical 6] {In the formula, R ¹ is a hydrogen atom, an alkyl group, a cycloalkyl group, a haloalkyl group, an alkoxyalkyl group, a benzyloxyalkyl group, a benzyl group, a phenyl group, a pyridyl group, a dialkylaminocarbonyl group, an alkoxycarbonyl group, an alkylsulfonyl group. , A phenylsulfonyl group, a dialkylaminosulfonyl group, a haloalkylcarbonyl group, an alkylcarbonyl group, a benzoyl group or an alkenyl group, R ² and R ³ are the same or different,
Hydrogen atom, halogen atom, alkyl group, cycloalkyl group, alkenyl group, alkoxycarbonylalkenyl group, alkynyl group, haloalkyl group, alkoxyalkyl group, alkoxycarbonylalkyl group, alkylcarbonylalkyl group, cycloalkylcarbonylalkyl group, cyanoalkyl group , A dialkylaminocarbonylalkyl group, a dialkylaminoalkyl group, a dialkylaminosulfonylalkyl group, an azidoalkyl group, a benzyl group, a phenyl group, a nitro group, a cyano group, an azido group, an amino group, a monoalkylamino group, a dialkylamino group,
A benzylamino group, an alkylcarbonylamino group which may be substituted with a halogen atom, a benzoylamino group, an alkoxycarbonylamino group, a phenoxycarbonylamino group, an alkylsulfonylamino group which may have an amino group substituted with an alkyl group, an amino group A phenylsulfonylamino group which may be substituted with an alkyl group, an alkylideneamino group, a benzylideneamino group, an optionally substituted tetrazolyl group, a formula —COR ⁴ (in the formula, R ⁴ is a hydrogen atom,
Hydroxyl group, alkyl group, cycloalkyl group, haloalkyl group, alkenyl group, alkynyl group, benzyl group, phenyl group, alkoxy group, haloalkoxy group, alkoxyalkoxy group, alkenyloxy group, haloalkenyloxy group, alkynyloxy group, benzyloxy Represents a group or a phenoxy group. ), A group represented by the formula: —C (O) NR ⁵
R ⁶ (wherein, ^{R 5} and ^{R 6} are the same or different and a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, a benzyl group, a phenyl group or an alkoxy group.), A group represented by the formula -SR ⁷ (In the formula, R ⁷ represents a hydrogen atom, an alkyl group or a haloalkyl group.), Formula -S
A group represented by O ₂ NR ⁵ R ⁶ (in the formula, R ⁵ and R ⁶ have the same meanings as described above), a formula —S (O) nR ⁸ (wherein n is an integer of 1 or 2). And R ⁸ represents an alkyl group, an alkenyl group, or a haloalkyl group), a group represented by the formula —OR ⁹ [wherein, R ⁹ represents a hydrogen atom, an alkyl group,
A cycloalkylalkyl group, an alkenyl group, an alkynyl group, a benzyl group (the group may be substituted with a halogen atom, an alkyl group or an alkoxy group), a haloalkyl group, a haloalkenyl group, a phenyl group (the group is a halogen atom, May be substituted with an alkyl group or an alkoxy group), an alkoxyalkyl group, an alkoxyalkoxyalkyl group, a haloalkoxyalkyl group, a benzyloxyalkyl group, a phenoxyalkyl group, an alkylthioalkyl group, a dialkylaminoalkyl group, an azidoalkyl group, Indicates an alkylcarbonyl group, haloalkylcarbonyl group, benzoyl group, dialkylaminocarbonyl group, cyanoalkyl group, alkylideneamino group, dialkylideneamino group, benzylideneamino group or alkoxycarbonylalkyl group. ] The group represented by or formula-C
(= NOR ¹⁰ ) R ¹¹ (wherein R ¹⁰ is a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, a benzyl group,
It represents a haloalkyl group or a phenyl group, and R ¹¹ represents a hydrogen atom, an alkyl group, a benzyl group, a haloalkyl group or a phenyl group. ), And R ² and R ³ may form a ring with an alkyl group which may contain a hetero atom. A
And B are the same or different and each represents an alkyl group, a haloalkyl group, an alkoxy group, a monoalkylamino group, a dialkylamino group, a halogen atom or a haloalkoxy group,
Z represents a methine group or a nitrogen atom, X represents an oxygen atom or a sulfur atom, and Y represents a hydrogen atom, an alkyl group or an alkoxyalkyl group. } The indazole sulfonyl urea derivative shown by these, and a formula [Ia] or "II-.
a]

[0007]

[Chemical 7] {In the formula, R ¹ is a hydrogen atom, an alkyl group, a cycloalkyl group, a haloalkyl group, an alkoxyalkyl group, a benzyloxyalkyl group, a benzyl group, a phenyl group, a pyridyl group, a dialkylaminocarbonyl group, an alkoxycarbonyl group, an alkylsulfonyl group. , A phenylsulfonyl group, a dialkylaminosulfonyl group, a haloalkylcarbonyl group, an alkylcarbonyl group, a benzoyl group or an alkenyl group, R ² and R ³ are the same or different,
Hydrogen atom, halogen atom, alkyl group, cycloalkyl group, alkenyl group, alkoxycarbonylalkenyl group, alkynyl group, haloalkyl group, alkoxyalkyl group, alkoxycarbonylalkyl group, alkylcarbonylalkyl group, cycloalkylcarbonylalkyl group, cyanoalkyl group , A dialkylaminocarbonylalkyl group, a dialkylaminoalkyl group, a dialkylaminosulfonylalkyl group, an azidoalkyl group, a benzyl group, a phenyl group, a nitro group, a cyano group, an azido group, an amino group, a monoalkylamino group, a dialkylamino group,
A benzylamino group, an alkylcarbonylamino group which may be substituted with a halogen atom, a benzoylamino group, an alkoxycarbonylamino group, a phenoxycarbonylamino group, an alkylsulfonylamino group which may have an amino group substituted with an alkyl group, an amino group A phenylsulfonylamino group which may be substituted with an alkyl group, an alkylideneamino group, a benzylideneamino group, an optionally substituted tetrazolyl group, a formula —COR ⁴ (in the formula, R ⁴ is a hydrogen atom,
Hydroxyl group, alkyl group, cycloalkyl group, haloalkyl group, alkenyl group, alkynyl group, benzyl group, phenyl group, alkoxy group, haloalkoxy group, alkoxyalkoxy group, alkenyloxy group, haloalkenyloxy group, alkynyloxy group, benzyloxy Represents a group or a phenoxy group. ), A group represented by the formula: —C (O) NR ⁵
R ⁶ (wherein, ^{R 5} and ^{R 6} are the same or different and a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, a benzyl group, a phenyl group or an alkoxy group.), A group represented by the formula -SR ⁷ (In the formula, R ⁷ represents a hydrogen atom, an alkyl group or a haloalkyl group.), Formula -S
A group represented by O ₂ NR ⁵ R ⁶ (in the formula, R ⁵ and R ⁶ have the same meanings as described above), a formula —S (O) nR ⁸ (wherein n is an integer of 1 or 2). And R ⁸ represents an alkyl group, an alkenyl group, or a haloalkyl group), a group represented by the formula —OR ⁹ [wherein, R ⁹ represents a hydrogen atom, an alkyl group,
A cycloalkylalkyl group, an alkenyl group, an alkynyl group, a benzyl group (the group may be substituted with a halogen atom, an alkyl group or an alkoxy group), a haloalkyl group, a haloalkenyl group, a phenyl group (the group is a halogen atom, May be substituted with an alkyl group or an alkoxy group), an alkoxyalkyl group, an alkoxyalkoxyalkyl group, a haloalkoxyalkyl group, a benzyloxyalkyl group, a phenoxyalkyl group, an alkylthioalkyl group, a dialkylaminoalkyl group, an azidoalkyl group, Indicates an alkylcarbonyl group, haloalkylcarbonyl group, benzoyl group, dialkylaminocarbonyl group, cyanoalkyl group, alkylideneamino group, dialkylideneamino group, benzylideneamino group or alkoxycarbonylalkyl group. ] The group represented by or formula-C
(= NOR ¹⁰ ) R ¹¹ (wherein R ¹⁰ is a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, a benzyl group,
It represents a haloalkyl group or a phenyl group, and R ¹¹ represents a hydrogen atom, an alkyl group, a benzyl group, a haloalkyl group or a phenyl group. ), And R ² and R ³ may form a ring with an alkyl group which may contain a hetero atom. }
And an intermediate thereof represented by the indazole sulfonamide derivative represented by and an herbicide containing indazole sulfonylurea as an active ingredient.

The compounds of the present invention include tautomers, geometric isomers and optical isomers.

In the present invention, the alkyl group means a straight chain or branched chain alkyl group having 1 to 30 carbon atoms, for example, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, Isobutyl group, sec-butyl group,
t-butyl group, n-pentyl group, isoamyl group, neopentyl group, n-hexyl group, isohexyl group, 3,3-
Dimethylbutyl group, n-heptyl group, 5-methylhexyl group, 4-methylhexyl group, 3-methylhexyl group,
4,4-dimethylpentyl group, n-octyl group, 6-methylheptyl group, n-nonyl group, 7-methyloctyl group, n-decyl group, 8-methylnonyl group, n-undecyl group, 9-methyldecyl group, n-dodecyl group, 10-methylundecyl group, n-tridecyl group, 11-methyldodecyl group, n-tetradecyl group, 12-methyltridecyl group, n-pentadecyl group, 13-methyl-tetradecyl group, n-hexadecyl group Group, n-heptadecyl group, n-
It includes an octadecyl group, an n-nonadecyl group, an n-eicosyl group and the like.

The alkoxy group and the alkylsulfonyl group are a (alkyl) -O- group and a (alkyl) -SO _2- group, respectively, the alkyl portions of which have the above meanings.

The halogen atom includes each atom of fluorine, chlorine, bromine and iodine.

The alkenyl group means a linear or branched alkenyl group having 2 to 20 carbon atoms, such as vinyl group,
Propenyl group, isopropenyl group, butenyl group, pentenyl group, hexenyl group, heptenyl group, octenyl group,
A 3-methyl-1-butenyl group, a 4-methyl-1-pentenyl group and the like are included.

The alkynyl group means a linear or branched alkynyl group having 2 to 20 carbon atoms, for example, ethynyl group, propynyl group, butynyl group, pentynyl group, hexynyl group, 3,3-dimethyl-1-. Butynyl group, 4-methyl-1-pentynyl group, 3-methyl-1-pentynyl group, 5-methyl-1-hexynyl group, 4-methyl-1-
A hexynyl group, a 3-methyl-1-hexynyl group, a heptynyl group, an octynyl group, a nonynyl group, a decynyl group, an undecynyl group, a dodecynyl group, a tridecynyl group, a tetradecynyl group, a pentadecynyl group, a hexadecynyl group and the like are included.

In the above formula [I] or [II], R ¹ is a hydrogen atom, a methyl group or an ethyl group, and R ² or R ³ are the same or different hydrogen atoms. , A halogen atom, an alkoxycarbonyl group, a dialkylaminocarbonyl group, an alkoxy group, a haloalkoxy group, an alkenyloxy group, a cyano group or a trifluoromethyl group, wherein A and B are the same or different from each other, a methoxy group, a methyl group or a haloalkoxy. Group, Z is a methine group or a nitrogen atom, X is an oxygen atom, and Y is a hydrogen atom.

Next, typical examples of the compounds of the present invention represented by the formula [I] or [II] are shown in Tables 1 and 2.
The compound numbers are referred to in the following description, and when R ¹ represents a hydrogen atom, tautomers represented by the formulas [I] and [II] can be taken.

The following notations in the tables in the present specification each represent a corresponding group.

Bn: benzyl group Pr: n-propyl group Pen: n-pentyl group Bu: n-butyl group Me: methyl group Ph: phenyl group Et: ethyl group

[0018]

[Table 1]

[0019]

[Table 1] (continued)

[0020]

[Table 1] (continued)

[0021]

[Table 1] (continued)

[0022]

[Table 1] (continued)

[0023]

[Table 1] (continued)

[0024]

[Table 1] (continued)

[0025]

[Table 1] (continued)

[0026]

[Table 1] (continued)

[0027]

[Table 1] (continued)

[0028]

[Table 1] (continued)

[0029]

[Table 1] (continued)

[0030]

[Table 1] (continued)

[0031]

[Table 1] (continued)

[0032]

[Table 1] (continued)

[0033]

[Table 1] (continued)

[0034]

[Table 1] (continued)

[0035]

[Table 1] (continued)

[0036]

[Table 1] (continued)

[0037]

[Table 1] (continued)

[0038]

[Table 1] (continued) * R ³ indicates 5th place

[0039]

[Table 1] (continued)

[0040]

[Table 1] (continued)

[0041]

[Table 1] (continued)

[0042]

[Table 1] (continued)

[0043]

[Table 1] (continued)

[0044]

[Table 1] (continued)

[0045]

[Table 1] (continued)

[0046]

[Table 1] (continued)

[0047]

[Table 1] (continued)

[0048]

[Table 1] (continued)

[0049]

[Table 1] (continued)

[0050]

[Table 1] (continued)

[0051]

[Table 1] (continued)

[0052]

[Table 1] (continued)

[0053]

[Table 1] (continued)

[0054]

[Table 1] (continued)

[0055]

[Table 1] (continued)

[0056]

[Table 1] (continued)

[0057]

[Table 1] (continued)

[0058]

[Table 1] (continued)

[0059]

[Table 1] (continued) * R ³ indicates 5th place

[0060]

[Table 1] (continued)

[0061]

[Table 2]

[0062]

[Table 2] (continued)

[0063]

[Table 2] (continued)

[0064]

[Table 2] (continued)

[0065]

[Table 2] (continued)

[0066]

[Table 2] (continued)

[0067]

[Table 2] (continued)

[0068]

[Table 2] (continued)

[0069]

[Table 2] (continued)

[0070]

[Table 2] (continued)

[0071]

[Table 2] (continued)

[0072]

[Table 2] (continued)

[0073]

[Table 2] (continued)

[0074]

[Table 2] (continued)

[0075]

[Table 2] (continued)

[0076]

[Table 2] (continued)

[0077]

[Table 2] (continued)

[0078]

[Table 2] (continued)

[0079]

[Table 2] (continued)

[0080]

[Table 2] (continued)

[0081]

[Table 2] (continued) * R ³ indicates 5th place

[0082]

[Table 2] (continued)

[0083]

[Table 2] (continued)

Examples of the method for producing the compound of the present invention include the following methods, but are not limited to these methods.

General methods for producing the compound [I] or [II] of the present invention are shown in the following <Production Method 1> to <Production Method 3>. <Manufacturing method 1>

[0086]

[Chemical 8] (In the formula, R ¹ , R ² , R ³ , A, B, Z, X and Y have the same meanings as described above.) That is, the compound of the present invention represented by the formula [I] or [II] is represented by the formula [I I-a] or [II-a] of the production intermediate of the present invention (the production method is described later, hereinafter referred to as an intermediate),
It can be produced by reacting with a compound represented by the formula [III].

This reaction is usually carried out in a solvent or in the absence of a solvent, optionally in the presence of a base, the reaction temperature is in the range of -20 ° C to the boiling point of the solvent, and the reaction time is in the range of 0.5 hour. The range is 24 hours. The amount of the compound used in the reaction is the intermediate 1 represented by the formula [Ia] or [II-a].
The amounts of the compound represented by the formula [III] and the base are independently 1 to 1.5 equivalents based on the equivalent amount.

As the solvent, aromatic hydrocarbons such as benzene, xylene and toluene, halogenated hydrocarbons such as chloroform, carbon tetrachloride, dichloroethane, chlorobenzene and dichlorobenzene, diethyl ether, dioxane, tetrahydrofuran (THF), Ethers such as isopropyl ether (IPE) and diethylene glycol dimethyl ether, methanol, ethanol, 2-
Alcohols such as propanol, esters such as ethyl acetate and butyl acetate, nitro compounds such as nitromethane and nitrobenzene, nitriles such as acetonitrile and isobutyronitrile, formamide, N, N-dimethylformamide (DMF), N, N -Dimethylacetamide (D
MAC), dimethyl sulfoxide (DMSO), N-methylpyridone (NMP), and other aprotic polar solvents can be exemplified.

As the base, pyridine, triethylamine, 1,4-diazabicyclo [2.2.2] octane,
1,8-diazabicyclo [5.4.0] -7-undecene (DBU), N, N-diethylaniline, diethyl-
Examples thereof include organic bases such as methylamine, inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate and sodium hydride, and alkali metal alkoxides such as sodium methoxide and sodium ethoxide.

The compound represented by the formula [III] is
A compound of the formula [IV] and phenyl chloroformate,
It can be produced by reacting phenyl chlorothio-O-phenyl formate or phenyl chlorodithioformate in a suitable solvent in the presence of a base. <Manufacturing method 2>

[0091]

[Chemical 9] (In the formula, R ¹ , R ² , R ³ , A, B, X, Y and Z have the same meanings as described above.) The compound of the present invention represented by the formula [I] or [II] has the formula [I- b] or [II-b] can be produced by reacting the compound of the formula [IV]. The compound represented by the formula [Ib] or [II-b] has the formula [Ia] or [I
It can be produced by reacting the intermediate represented by Ia] with phosgene or thiophosgene in a suitable solvent.

This reaction is usually carried out in a solvent or in the absence of a solvent in the presence of a base as necessary, and the reaction temperature range, reaction time range, solvent and base used in the reaction are the same as in <Production Method 1>. is there. The amount of the compound to be subjected to the reaction is 1 to 1.5 equivalents of the compound represented by the formula [Ib] or [II-b] and the amount of the compound represented by the formula [IV] and the base are independently 1 to 1.5. It is equivalent. <Manufacturing method 3>

[0093]

[Chemical 10] (In the formula, R ¹ , R ² , R ³ , A, B, X, Y and Z have the same meanings as described above.) The compound of the present invention represented by the formula [I] or [II] is represented by the formula [I
-C] or [II-c] and a compound of formula [IV]
It can be produced by reacting with a compound represented by. The compound represented by the formula [Ic] or [II-c] is obtained by converting the intermediate represented by the formula [Ia] or [II-a] into phenyl chloroformate, chlorothio-O-phenyl formate or phenylchlorodithioformate. It can be produced by reacting in a suitable solvent in the presence of a base, and can also be produced by reacting a compound represented by the formula [Ib] or [II-b] with phenol or thiophenol. .

This reaction is usually carried out in a solvent or in the absence of a solvent in the presence of a base as necessary, and the reaction temperature range, reaction time range, solvent and base used in the reaction are the same as in <Production Method 1>. is there. With respect to the amount of the compound used in the reaction, the amount of the compound represented by the formula [IV] and the amount of the base are independently 1 to 1.5 with respect to 1 equivalent of the compound represented by the formula [Ic] or [II-c]. It is equivalent. In addition, the production method of the formula [Ia] which is an intermediate for producing the compound of the present invention is referred to as <intermediate production method 1>, and the production method of the formula [II-a] is referred to as <intermediate production method. 2>, but the invention is not limited thereto. <Production Method 1 of Intermediate> Production of Formula [Ia]

[0095]

[Chemical 11] (In the formula, R ¹ represents a hydrogen atom, an alkyl group, a benzyl group or a phenyl group, and R ² and R ³ represent a hydrogen atom, an alkyl group, a halogen atom, a nitro group, an alkoxy group, a haloalkoxy group or a haloalkyl group. , L represents a halogen atom.) That is, a compound represented by the formula [V] is reacted with the hydrazine derivative of the formula [V] in DMSO, for example.
[I] and further producing a diazonium salt in concentrated hydrochloric acid, which is reacted with sulfurous acid gas in a solvent such as acetic acid in the presence of copper chloride to give a compound of the formula [VI
I] can be produced. This is reacted with an excess of t-butylamine to produce a compound represented by the formula [Id], and then the compound of the formula [Id] is treated with an excess of trifluoroacetic acid to give t.
By removing the -butyl group, the intermediate represented by the formula [Ia] can be produced. <Production Method 2 of Intermediate> Production of Formula [II-a]

[0096]

[Chemical 12] (In the formula, R ¹ represents an alkyl group, a haloalkyl group, a benzyl group or a phenyl group, and R ² and R ³ represent a hydrogen atom, an alkyl group, a halogen atom, an alkoxy group, a phenyl group,
A benzyl group or a haloalkoxy group is shown. That is, the compound represented by the formula [IX] is obtained by reacting the compound represented by the formula [VIII] with n-butyllithium in ether in the temperature range of −40 to −20 ° C., and then by blowing a sulfurous acid gas. It can be manufactured. The intermediate represented by the formula [II-a] can be prepared by adding the intermediate represented by the formula [I-a] to a mixed aqueous solution of hydroxylamine-O-sulfonic acid and a base under ice cooling.
X] can be produced by adding an aqueous solution of a compound represented by the formula [X].

The compound represented by the formula [VIII] in this reaction formula is [Liebigs Ann. Chem. , 908
(1980)], [Org. Synth. Coll.
Vol. V, 650], [J. Chem. Soc. Pe
rkin Trans. II, 1695, (197
5)], [Org. Synth. Coll. Vol.
V, 941], etc.

The intermediate represented by the formula [Ia] or [II-a] can also be produced by the method shown below. <Production Method 3 of Intermediate> Production of Formula [I-a] or [II-a]

[0099]

[Chemical 13] (In the formula, R ¹ is an alkyl group, a cycloalkyl group, a haloalkyl group, an alkoxyalkyl group, a benzyloxyalkyl group, a benzyl group, a dialkylaminocarbonyl group,
An alkoxycarbonyl group, an alkylsulfonyl group, a phenylsulfonyl group, a dialkylaminosulfonyl group, a haloalkylcarbonyl group, an alkylcarbonyl group, a benzoyl group or an alkenyl group, wherein R ² or R ³ is a hydrogen atom, a halogen atom, an alkoxy group or a haloalkoxy. Group, haloalkyl group, alkoxycarbonyl group, phenyl group or benzyl group, L represents a halogen atom,
M represents a bromine atom or a chlorine atom. ) That is, the compound represented by the formula [X] is N-in carbon tetrachloride.
The compound represented by the formula [XI] can be produced by reacting bromosuccinimide, N-chlorosuccinimide, or bromine or chlorine in the presence of light or a radical reaction initiator. A compound represented by the formula [XII] is produced by reacting a compound represented by the formula [XI] with thiourea, and the compound represented by the formula [XII] is treated with chlorine or bromine in a mixed solution of acetic acid and water. After producing the compound of the formula [XIII] by reacting it, it is reacted with t-butylamine to produce the compound of the formula [XI
V] can be produced. Expression [X
The compound of formula [XV] can be produced by reducing the compound of formula [IV]. The compound represented by the formula [XV] can be reacted with isoamyl nitrite and then reacted with hydrochloric acid to produce the compound represented by the formula [XVI]. By reacting the compound represented by the formula [XVI] with, for example, an alkyl halide or a benzyl halide, the compound represented by the formula [Id] or [II-d] can be produced.

Formulas [XVI], [Id] or [II-
The compound represented by the formula [d] is the compound represented by the formula [XVII] by removing the t-butyl group with trifluoroacetic acid, and the compound represented by the formula [I-
a] or an intermediate represented by [II-a], respectively.

Further, by reacting the compound of the formula [XVII] with R ¹ L (wherein R ¹ and L have the same meanings as defined above), the compound of the formula [Ia] is obtained.
And an intermediate represented by [II-a] can be produced.

The intermediate represented by the formula [Ia] has various production methods depending on, for example, the kind of the substituent, but the following <Intermediate production method 4> and <Intermediate production method 5-1 to 3>. It can also be produced by the method shown in. <Manufacturing method 4 of intermediates>

[0103]

[Chemical 14] (In the formula, R ¹ represents a hydrogen atom, an alkyl group, a benzyl group or a phenyl group, R ² represents a halogen atom, preferably a fluorine atom, R ³ has the same meaning as described above, and R ⁴ represents an alkoxy group or an alkoxy group. Alkoxy group, benzyloxy group, cycloalkylalkoxy group, haloalkoxy group,
A dialkylaminoalkoxy group, an alkylthio group, an alkylamino group, a dialkylamino group, and a benzylamino group are shown. ) That is, the intermediate represented by the formula [I-a] or [II-a] in the present reaction scheme is treated with a polar solvent such as DMSO, DMF, DMAC and NMP in sodium hydride, potassium hydride, potassium carbonate and potassium. Is it reacted with a compound represented by the formula R ⁴ —H (wherein R ⁴ has the same meaning as defined above) in the presence of a base such as t-butoxide, sodium hydroxide or potassium hydroxide. , Formula R ⁴ Na (wherein R
⁴ has the same meaning as defined above. Or a compound represented by the formula R ⁴ K (wherein R ⁴ has the same meaning as defined above) and reacted with a compound of the formula [Ie]
Alternatively, each of the intermediates represented by [II-e] can be produced. <Manufacturing Method 5-1 of Intermediate>

[0104]

[Chemical 15] (In the formula, R ¹ represents an alkyl group, a benzyl group or a phenyl group, R ³ has the same meaning as described above, R ⁵ represents an alkyl group, a benzyl group, an alkenyl group, an alkynyl group, a haloalkenyl group, a haloalkyl group, An alkoxyalkyl group,
An alkoxycarbonylalkyl group and a cyanoalkyl group are shown, and L ¹ is a halogen atom, an alkylsulfonyloxy group, a haloalkylsulfonyloxy group, and an optionally substituted benzenesulfonyloxy group. ) That is, the intermediate represented by the formula [If] or [II-f] in the present reaction formula is added to the formula R ⁵ -L in the presence of a base in a suitable solvent.
¹ (wherein R ⁵ and L ¹ have the same meanings as defined above) and reacted with a compound of the formula [I-
g] or the intermediate represented by [II-g] can be produced, respectively.

The intermediate represented by the formula [If] or [II-f] can be produced by the following method.

[0106]

[Chemical 16] (In the formula, R ¹ represents an alkyl group, a benzyl group or a phenyl group, R ² represents a halogen atom, preferably a fluorine atom, and R ³ represents a hydrogen atom, a halogen atom, an alkyl group, a haloalkyl group, a haloalkoxy group or an alkoxy. Group, and R ⁸ represents an alkyl group, a benzyl group or a cycloalkylalkyl group, preferably a cyclopropylmethyl group.) That is, the intermediate represented by the formula [Ia] or [II-a] in the present reaction scheme. In a suitable solvent in the presence of a base of formula R ⁸ —O
Reacting with a compound of formula H (wherein R ⁸ has the same meaning as defined above) to produce an intermediate of formula [I-h] or [II-h], Further deprotection can produce an intermediate represented by the formula [If] or [II-f], respectively. <Process for producing intermediate 5-2>

[0107]

[Chemical 17] (In the formula, R ¹ represents an alkyl group, a benzyl group or a phenyl group, and R ³ and R ⁵ have the same meanings as described above.) That is, in this reaction formula, the formulas [If] and [II-f] are used. The compound represented by the formula R ⁵ —OH (R ⁵ has the same meaning as described above) in a suitable solvent is used as an intermediate for the Mitsunobu reaction [(Organic Reactions Vol.
42, p. 335) Description] is carried out to obtain the formula [I-
g] or the intermediate represented by [II-g] can be produced, respectively. <Manufacturing Method 5-3 of Intermediate>

[0108]

[Chemical 18] (In the formula, R ¹ represents an alkyl group, a benzyl group or a phenyl group, and R ³ , R ⁵ and L ¹ have the same meanings as described above,
R ⁶ represents an alkyl group, preferably a methyl group. ) That is, the intermediate represented by the formula [If] or [II-f] in the present reaction formula is reacted with acetal of DMF to give the compound represented by the formula [I
-I] or [II-i] is prepared, and the compound of formula R ⁵ -L ¹ (in the formula, R ⁵
And L ¹ have the same meaning as defined above. ) With a compound of formula [I-j] or [II
-J] is produced, and these are hydrolyzed with an acid or an alkali to give a compound of the formula [Ig] or [II-
An intermediate represented by g] can be produced.

Next, Table 3 lists specific compounds of the intermediates represented by the formula [Ia] or [II-a].

[0110]

[Table 3]

[0111]

[Table 3] (continued)

[0112]

[Table 3] (continued)

[0113]

[Table 3] (continued)

[0114]

[Table 3] (continued)

[0115]

[Table 3] (continued)

[0116]

[Table 3] (continued)

[0117]

[Table 3] (continued)

[0118]

[Table 3] (continued)

[0119]

[Table 3] (continued)

Next, the present invention will be explained concretely by describing the production method of the intermediate and the production method of the compound of the present invention as Production Examples.

<Production Example 1> 1-Methyl-4-fluoro-1H-indazole-3-
Preparation of Sulfonamide (Intermediate No. 24) 75 g (539 mmol) of 2,6-difluorobenzonitrile was added to 300 ml of DMSO, and 33 g (716 mmol) of methylhydrazine was added dropwise thereto with stirring.
The reaction proceeded exothermically, and the dropping was continued while maintaining the temperature at 80 to 100 ° C. After returning to room temperature, the mixture was poured into a large excess of cold water, the crystals were filtered off, air-dried, and 3-amino-1-methyl-4-fluoro-1H-indazole (compound represented by the formula [VI]) (pale yellow crystals). ) 72 g (yield 81%) was obtained.

Then, 70 g (424 mmol) of 3-amino-1-methyl-4-fluoro-1H-indazole was added.
Was dissolved in 200 ml of acetic acid, and 140 ml of concentrated hydrochloric acid was added. This is vigorously stirred, and 33 g (478 mmol) of sodium nitrite is added to 60 ml of water in the range of -5 to -10 ° C.
The solution dissolved in was gradually added dropwise. The diazonium salt solution thus obtained was preliminarily blown with 370 ml of acetic acid until sulfurous acid gas was saturated (120 g) to which 17 g (100 mmol) of cupric chloride dihydrate was added.
The mixture was gradually added dropwise in the range of 5 to -10 ° C. After completion of the dropwise addition, stirring was continued for 1 hour at 0 ° C. or lower, then, the mixture was poured into a large excess of cold water, the crystals were collected by filtration and air-dried, and 1-methyl-4-fluoro-1H-indazole-3-sulfonyl chloride (formula Compound represented by [VII]) (pale purple crystal) 70
g (yield 66%) was obtained.

Further, 1-methyl-in 50 ml of THF
4-Fluoro-1H-indazole-3-sulfonyl chloride (13.9 g, 56 mmol) was added to THF (100 m).
12.9 g (177 mmol) of t-butylamine in 1
In addition, the mixture was stirred overnight at room temperature. After completion of the reaction, the mixture was poured into a large excess of water, the crystals were collected by filtration and air-dried, and 3- (Nt-butylsulfamoyl) -1-methyl-4-fluoro-1H-indazole (the formula [Id] was used). 15.9 g (yield 99.6%) of the compound shown (light purple crystal) was obtained.

3- (Nt-butylsulfamoyl)-
15 g of 1-methyl-4-fluoro-1H-indazole
(53 mmol) was added to 50 ml of trifluoroacetic acid and stirred overnight. After completion of the reaction, trifluoroacetic acid was distilled off under reduced pressure and washed with n-hexane, and 10.5 g of 1-methyl-4-fluoro-1H-indazole-3-sulfonamide (light purple crystal) (yield 86. 8%). Melting point 22
1-223 ° C

PRODUCTION EXAMPLE 2 1- (1-Methyl-4-fluoro-1H-indazol-3-sulfonyl) -3- (4,6-dimethoxypyrimidin-2-yl) urea (Compound No. I-26) 1-Methyl-4-fluoro-1H-obtained in <Production Example 1>
To a solution of 0.5 g (2.3 mmol) of indazole-3-sulfonamide and 0.62 g (2.3 mmol) of phenyl (4,6-dimethoxypyrimidin-2-yl) carbamate in 20 ml of acetonitrile was added DBU0.35.
g (2.3 mmol) was added, and the mixture was stirred at room temperature for 12 hours. The mixture was poured into ice water, acidified with citric acid, and the generated crystals were collected by filtration and washed with ice water, IPE, and ether to obtain 0.49 g of the desired product (colorless needle crystals) (yield 52%). Melting point: 205-209 ° C

<Production Example 3-1> Production of methyl 2-bromomethyl-3-nitrobenzoate (compound represented by the formula [XI]) Methyl 2-methyl-3-nitrobenzoate 98 g
(0.5 mol), N-bromosuccinimide 100 g
A suspension of (0.56 mol) of benzoyl peroxide and 1 g of carbon tetrachloride (800 ml) was refluxed for 3 days under irradiation with light of 500W. After cooling to room temperature, it was filtered and the filtrate was concentrated. Ether (200 ml) and IPE (200 ml) were added to the residue, and the produced crystals were filtered to give 121 g of the desired product (yield 88.
3%) was obtained. Melting point: 65-67 ° C

<Production Example 3-2> S- (2-methoxycarbonyl-6-nitrobenzyl)
Production of thiouronium bromide (compound represented by formula [XII]) 207 g (0.76 mol) of the product from <Production Example 3-1> and 57.6 g of thiourea in methanol (2 liters).
(0.76 mol) was refluxed for 12 hours. After cooling, methanol was distilled off, ethyl acetate (1 liter) was added to the residue, and the product was filtered. This was used in the next reaction without purification. Yield: 246 g (yield 93%)

<Production Example 3-3> Methyl 2- (t-butylaminosulfonylmethyl)-
Production of 3-nitrobenzoate (compounds represented by formula [XIII] and formula [XIV]) <Production Example 3 in water (2 liters) and acetic acid (1 liter)
110 g (0.32 mol) of the product from -2> were cooled to 5 ° C and chlorine was blown in at 5 to 10 ° C for 4 hours. After stirring at room temperature for 1 hour, the product was filtered, washed with ice water and dissolved in 1 liter of dichloromethane. 54 g (0.74 mol) of t-butylamine was added dropwise thereto at 0 to 5 ° C, and then the mixture was stirred at room temperature for 2 hours. After washing the organic layer with water, concentrating it, adding IPE to the residue and collecting by filtration to obtain 63 g of the desired product.
(Yield 60.1%) was obtained. This was used in the next reaction without purification.

<Production Example 3-4> Production of methyl 3-amino-2- (t-butylaminosulfonylmethyl) -benzoate (compound represented by the formula [XV]) Product from <Production Example 3-3> A solution of 48 g (0.145 mol) and 164 g (0.73 mol) of stannous chloride dihydrate in 300 ml of ethanol was refluxed for 2 hours. After cooling, powder sodium bicarbonate (500 g) was gradually added to 2 liters of ethyl acetate. The generated salt is filtered, washed well with ethyl acetate, and the organic layer is concentrated to give the desired product 3
5.9 g (yield 82.4%) was obtained. Melting point: 123-1
25 ° C

<Production Example 3-5> Methyl 3- (t-butylaminosulfonyl) -1H-
Production of Indazole-4-carboxylate (Formula [XV
Compound represented by I]) 30 g (0.1 mol) of the product from <Production Example 3-4>,
Acetic anhydride 30.6 g (0.3 mol), potassium acetate 10
A suspension of g (0.102 mol) of benzene (500 ml) was heated to 80 ° C., and isoamyl nitrite 17.6 was added at the same temperature.
g (0.15 mol) was added dropwise. After refluxing for a further 12 hours, it was cooled and the salts were filtered off. The organic layer was concentrated, methanol (500 ml) and 10% hydrochloric acid (20 ml) were added to the residue, and the mixture was refluxed for 1 hour. After the methanol was distilled off, water was added and the mixture was neutralized with an aqueous sodium hydrogen carbonate solution, and the formed crystals were collected by filtration to obtain 29.3 g of the desired product (yield 94.1%). Melting point: 218-220 ° C

<Production Example 3-6> Methyl 3- (t-butylaminosulfonyl) -1-methyl-1H-indazole-4-carboxylate and methyl 3- (t-butylaminosulfonyl) 2-methyl-2H-. Production of Indazol-4-carboxylate (Compounds of the Formulas [Id] and [II-d]) 10 g (32 mmol) of the product from <Production Example 3-5>, potassium carbonate 6 6.8 g (48 ml) of methyl iodide was added to a solution of 6.6 g (48 mmol) of methanol (200 ml).
(Mmol) and refluxed for 3 hours. Methanol was distilled off, water was added to the residue, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, concentrated and purified by silica gel chromatography, methyl 3- (t-
Butylaminosulfonyl) -1-methyl-1H-indazole-4-carboxylate 5.9 g (yield 56.8)
%; Melting point: 189-190 ° C.) and methyl 3- (t-
Butylaminosulfonyl) 2-methyl-2H-indazol-4-carboxylate 2.1 g (yield 19.8
%; Melting point: 147-148 ° C.).

Production Example 4 Production of 2-Methyl-2H-indazole-3-sulfonamide (Intermediate No. 148) A solution of 9.5 g (72 mmol) of 2-methyl-2H-indazole in 200 ml of ether was added at -30 ° C. Cooled to n
-Butyl lithium (15% hexane solution) 61.4 g
(144 mmol) was added dropwise. After stirring at the same temperature for 1 hour, an excessive amount of sulfurous acid gas was blown at −20 ° C. or lower for 3 hours. After the reaction was completed, the temperature was returned to room temperature, the mixture was stirred for 12 hours, diluted with ether, and the product was filtered. The crystals were dried to obtain crude lithium 2-methyl-2H-indazole-3-sulfinate. This was used in the next reaction without purification.

A solution of 17.2 g (430 mmol) of sodium hydroxide in water (300 ml) was cooled with ice (below 10 ° C.).
Hydroxylamine-O-sulfonic acid 48.8 g (43
0 mmol) was added in small portions. Crude lithium 2-methyl-2H-indazole-3-synthesized with this solution previously
After adding to a solution of sulfinate in water (100 ml) at once, the mixture was stirred at room temperature for 12 hours. The generated crystals were collected by filtration to give 8.8 g of 2-methyl-2H-indazole-3-sulfonamide (pale yellow granular crystals) (yield 58%).
Got Melting point: 181-183 ° C

<Production Example 5> Production of 1- (2-methyl-2H-indazole-3-sulfonyl) -3- (4,6-dimethoxypyrimidin-2-yl) urea (Compound No. II-23) <Production> 2-Methyl-2H-indazole-obtained in Example 4>
To a solution of 3.2 g (15 mmol) of 3-sulfonamide and 4.1 g (15 mmol) of phenyl (4,6-dimethoxypyrimidin-2-yl) carbamate in acetonitrile (50 ml), 2.3 g of DBU (15 mmol).
Was added and the mixture was stirred at room temperature for 12 hours. Pour into ice water, acidify with citric acid, collect the resulting crystals by filtration, ice water, IP
E, washed with ether to give the desired product (colorless needle crystals) 4.
0 g (yield 68%) was obtained. Melting point: 199-202 ° C

<Production Example 6> 4-methoxy-1-methyl-1H-indazole-3-
Preparation of Sulfonamide (Intermediate No. 65) 4-Fluoro-1-methyl-1H-indazole-3-
Sulfonamide 5 g (21.8 mmol) and sodium methoxide 12.6 g (28% methanol solution) (6
A solution of 5 mmol) in DMSO (50 ml) was stirred at 130 ° C. for 1 hour. After confirming the disappearance of the raw materials by thin layer chromatography (TLC), the mixture was poured into ice water, the crystals produced by acidification with citric acid were collected by filtration, washed with water and IPE,
3.2 g (yield 60.9%) of the desired product was obtained. Melting point 268
-270 ° C

<Production Example 7> 4-Ethylthio-2-methyl-2H-indazole-3
-Preparation of sulfonamide (intermediate number 130) 4.8 g (77 mmol) of ethanethiol was added to a DMSO (70 ml) solution of 8.6 g (77 mmol) of potassium t-butoxide under water cooling, and further 4-fluoro-2. 8 g (35 mmol) of -methyl-2H-indazole-3-sulfonamide were added. 120 this mixture
After stirring for 2 hours at ℃ and confirming the disappearance of the raw materials by TLC,
The same treatment as in <Production Example 6> was carried out to obtain 6.8 g of the desired product (yield 7
2.5%) was obtained. Melting point 145-147 ° C

Preparation Example 8-1 Preparation of 4-Cyclopropylmethoxy-2-methyl-2H-indazole-3-sulfonamide (Intermediate No. 254) 60% sodium hydride (2.8 g, 70 mmol) was added to D
Suspended in 50 ml MSO and cyclopropanemethanol 6
g (83 mmol) was added dropwise, and the mixture was stirred at room temperature for 1 hour and then 4
-Fluoro-2-methyl-2H-indazole-3-sulfonamide 5.4 g (24 mmol) was added and 130
The mixture was stirred at 0 ° C for 3 hours. After the reaction, the mixture was poured into ice water, acidified with citric acid, extracted with ethyl acetate, the organic layer was washed with water and concentrated, and the formed crystals were collected by filtration, washed with IPE and dried to obtain 5.8 g of the desired product (yield 90%). Melting point: 139-1
41 ° C

<Production Example 8-2> 4-Hydroxy-2-methyl-2H-indazole-3
-Preparation of sulfonamide (Intermediate No. 189) 4-cyclopropylmethoxy-2-methyl-2H-indazole-3-sulfonamide 62 g (221 mmol), acetic acid 120 ml, concentrated hydrochloric acid 120 ml 8
Stirred at 0 ° C. for 1 hour. After acetic acid / hydrochloric acid was concentrated, the mixture was poured into ice water, the crystals were filtered and washed with water. Further, it was washed with IPE and dried to obtain 35.1 g of the desired product (yield 70%). Melting point 180-181 ° C

<Production Example 8-3> 4-allyloxy-2-methyl-2H-indazole-
Preparation of 3-Sulfonamide (Intermediate No. 203) 4-Hydroxy-2-methyl-2H-indazole-3
1.3 g of allyl bromide was added to a mixture of 5 g (22 mmol) of sulfonamide and 1.9 g (22 mmol) of sodium hydrogencarbonate in 50 ml of DMF, and the mixture was stirred at room temperature for 12 hours. The mixture was poured into ice water, acidified with citric acid, extracted with ethyl acetate, the organic layer was washed with water, concentrated, and purified by column chromatography (hexane: ethyl acetate = 2/1) to obtain 1.9 g of the desired product (yield 32 .5%) was obtained. Melting point 1
43-144 ° C

<Production Example 9> Production of 4- (2-chloroethoxy-2-methyl-2H-indazole-3-sulfonamide (intermediate number 229) (Mitsunobu reaction) 4-hydroxy-2-methyl-2H- Indazole-3
-To a solution of 5 g (22 mmol) of sulfonamide, 1.8 g (22 mmol) of 2-chloroethanol and 5.8 g (22 mmol) of triphenylphosphine in 50 ml of THF was added 3.8 g (22 mmol) of diethyl azodicarboxylate. The mixture was stirred at room temperature for 20 hours. Pour into water and extract with ethyl acetate. Wash the organic layer with water and concentrate, then perform column chromatography (hexane: ethyl acetate = 2/1).
The desired product (1.66 g, yield 26%) was obtained. Melting point 177-179 ° C

<Production Example 10-1> N ¹ , N ¹ -dimethyl-N ² -[(4-hydroxy-2-
Methyl-2H-indazol-3-yl) sulfonyl]
Production of formamidine (compound represented by the formula [II-i]) 4-hydroxy-2-methyl-2H-indazole-3
-21.3 g (174 mmol) of dimethylformamide dimethylacetal was added dropwise to a solution of 33 g (145 mmol) of sulfonamide in 200 ml of acetonitrile at room temperature. After stirring for 1 hour, the mixture was poured into ice water and extracted with ethyl acetate. The organic layer was washed with water, concentrated, and purified by column chromatography to obtain 35.2 g of the desired product (yield 86.3%). Melting point: 118-119 ° C

Production Example 10-2 Production of N ¹ , N ¹ -dimethyl-N ² -{[4- (2-fluoroethoxy) -2-methyl-2H-indazol-3-yl] sulfonyl} formamidine (Formula [II-
j]] 60% sodium hydride 0.6 g (15 mmol) D
N ¹ to MF50ml suspension, N ¹ - dimethyl -N ² -
[(4-Hydroxy-2-methyl-2H-indazol-3-yl) sulfonyl] formamidine 4.2 g (1
(5 mmol) was added and the mixture was stirred at room temperature for 1 hour. 1 more
-Brom-2-fluoroethane (2 g, 16 mmol) was added, and the mixture was stirred at room temperature for 12 hours. The crystals formed by pouring into ice water were collected by filtration and washed with water and IPE to obtain the desired product. This was used for the next reaction without purification. Yield 3.4g
(Yield 69.5%)

<Production Example 10-3> 4- (2-Fluoroethoxy) -2-methyl-2H-indazole-3-sulfonamide (Intermediate No. 230)
Preparation of N ¹ , N ¹ -dimethyl-N ² -{[4- (2-fluoroethoxy) -2-methyl-2H-indazol-3-yl] sulfonyl} formamidine 3.4 g (10.4 mmol), A mixture of 5 ml of concentrated hydrochloric acid and 50 ml of ethanol was refluxed for 12 hours. After confirming the disappearance of the raw materials by TLC, ethanol was distilled off, water was added and the generated crystals were collected by filtration and washed with water and IPE to obtain 2.4 g of the desired product (yield 85
%) Was obtained. Melting point 178-180 ° C

<Production Example 11> Production of 4-chloro-2-methyl-2H-indazole-3-sulfonamide (intermediate number 143) 4-chloro-1H-indazole 36.1 g (0.24)
Was added to a solution of 28.4 g (0.7 mol) of sodium hydroxide in 500 ml of methanol, and methyl iodide 85.
2 g (0.6 mol) was added dropwise. After heating under reflux for 4 hours, methanol was distilled off, water was added to the residue, and the mixture was extracted with dichloromethane. The organic layer was washed with water, dried and concentrated to give 4-chloro-1-methyl-1H-indazole and 4-chloro-
A mixture of 2-methyl-2H-indazole was obtained. This is subjected to silica gel column chromatography (ethyl acetate:
Separated with hexane = 4: 1) and 4-chloro-2-methyl-
2H-indazole (yellow liquid, refractive index (20 ° C.) 1.
6095) (17.4 g, yield 43.6%) was obtained.

A solution of 16 g (0.1 mol) of 4-chloro-2-methyl-2H-indazole in 300 ml of ether was cooled to -30 ° C., and 85.4 g (0.2% of hexane solution of n-butyllithium) (0.2%). Mol) was added dropwise. After stirring at the same temperature for 1 hour, an excessive amount of sulfurous acid gas was blown at −20 ° C. or lower for 3 hours. After the reaction was completed, the temperature was returned to room temperature, the mixture was diluted with ether, and the product was filtered. The crystals are dried and crude lithium 4-chloro-2-methyl-2H-indazole-3
-Sulfinate was obtained. This was used in the next reaction without purification.

To a solution of 16 g (0.4 mol) of sodium hydroxide in water (300 ml), 45.2 g (0.4 mol) of hydroxylamine-O-sulfonic acid was added little by little under ice cooling (<10 ° C.). Crude lithium synthesized from this solution
4-Chloro-2-methyl-2H-indazole-3-sulfinate was added in one portion to a solution of water (100 ml).
The mixture was stirred as it was at room temperature for 12 hours. The resulting crystals were collected by filtration to give 4-chloro-2-methyl-2H-indazole-3-sulfonamide (light yellow granular crystals) of the desired product 17.
1 g (yield 69.8%) was obtained. Melting point: 173-175
℃

<Production Example 12> 1- (4-chloro-2-methyl-2H-indazole-
Preparation of 3-sulfonyl) -3- (4,6-dimethoxypyrimidin-2-yl) urea (Compound No. II-134) 4-chloro-2-methyl-2H-obtained in <Production Example 11>.
Indazole-3-sulfonamide 0.8 g (3.3 mmol), phenyl (4,6-dimethoxypyrimidin-2-yl) carbamate 0.9 g (3.3 mmol)
0.5 g of DBU in acetonitrile (50 ml) solution of
(3.3 mmol) was added, and the mixture was stirred at room temperature for 12 hours. The mixture was poured into ice water, acidified with citric acid, and the formed crystals were collected by filtration and washed successively with water, isopropyl ether and ether, and then 1.2 g of the desired product (colorless needle crystals) (yield 85
%) Was obtained. Melting point: 171-172 ° C

The herbicide of the present invention has the general formula [I] or [I
I] is an indazolesulfonylurea derivative as an active ingredient.

When the compound of the present invention is used as a herbicide, the compound of the present invention may be used as it is, but a carrier, a surfactant, a dispersant, an auxiliary agent or the like which is generally used for formulation is blended. It can also be used by formulating into a powder, a wettable powder, an emulsion, a fine granule or a granule.

[0150] The carriers used for formulation include
For example Sieglite, talc, bentonite, clay,
Examples thereof include solid carriers such as kaolin, diatomaceous earth, white carbon, vermiculite, calcium carbonate, slaked lime, silica sand, ammonium sulfate and urea, and liquid carriers such as isopropyl alcohol, xylene, cyclohexane and methylnaphthalene.

Examples of the surfactants and dispersants include metal salts of alkylbenzene sulfonic acid, metal salts of dinaphthylmethane disulfonic acid, alcohol sulfate salts, alkylaryl sulfonates, lignin sulfonates, polyoxyethylene glycol ethers and poly (ethylene glycol) ethers. Examples thereof include oxyethylene alkyl aryl ether and polyoxyethylene sorbitan monoalkylate. Examples of the auxiliary agent include carboxymethyl cellulose, polyethylene glycol, gum arabic and the like. Before use, dilute to an appropriate concentration and spray or apply directly.

The herbicide of the present invention can be used by foliage application, soil application or water surface application. The blending ratio of the active ingredient is appropriately selected according to need, but in the case of powder or granule, it is appropriately selected from the range of 0.01 to 10% (weight), preferably 0.05 to 5% (weight). Is good. When used as an emulsion or wettable powder, 1-50%
(Weight), preferably 5 to 30% (weight).

The application rate of the herbicide of the present invention varies depending on the type of compound used, target weeds, development tendency, environmental conditions and dosage form used, but when it is used as it is as in powders and granules, The active ingredient may be appropriately selected from the range of 0.1 g to 5 kg, preferably 1 g to 1 kg per 10 ares. When it is used as a liquid such as an emulsion and a wettable powder, it is 0.1 to 50,000 p.
pm, preferably in the range of 10 to 10,000 ppm.

The compound of the present invention may be mixed with insecticides, fungicides, other herbicides, plant growth regulators, fertilizers and the like, if necessary.

Next, the formulation method will be specifically described with reference to typical formulation examples. The types and compounding ratios of the compounds and additives are not limited to these, and can be changed in a wide range. In the following description, “part” means part by weight.

<Formulation Example 1> Wettable powder 0.5 parts of polyoxyethylene octyl phenyl ether, 10 parts of compound I-91 or II-26, and 0.3 parts of sodium salt of β-naphthalenesulfonic acid formalin condensate.
5 parts, 20 parts of diatomaceous earth, 69 parts of clay are mixed and ground,
Obtain a wettable powder.

Formulation Example 2 Wettable Powder: 0.5 part of polyoxyethylene octylphenyl ether, 0.5 part of β-naphthalenesulfonic acid formalin condensate sodium salt in 10 parts of compound I-63 or II-134. , 20 parts of diatomaceous earth, 5 parts of white carbon,
64 parts of clay is mixed and ground to obtain a wettable powder.

Formulation Example 3 Wettable Powder 10 parts of compound I-134 or II-104, 0.5 part of polyoxyethylene octyl phenyl ether, β-
0.5 parts of naphthalenesulfonic acid formalin condensate sodium salt, 20 parts of diatomaceous earth, 5 parts of white carbon,
64 parts of calcium carbonate are mixed and ground to obtain a wettable powder.

Formulation Example 4 Emulsion 60 parts of an equal mixture of xylene and isophorone in the compound I-92 or II-64 part, a surfactant polyoxyerylene sorbitan alkylate, a polyoxyethylene alkylaryl polymer and an alkylaryl sulfonate. An emulsion is obtained by adding 10 parts of the above mixture and stirring them well.

Formulation Example 5 Granules 10 parts of compound I-64 or II-142, 80 parts of a bulking agent in which talc and bentonite are mixed at a ratio of 1: 3,
To 5 parts of white carbon, 5 parts of a mixture of surfactant polyoxyethylene sorbitan alkylate, polyoxyethylene alkylaryl polymer and alkylaryl sulfonate, 10 parts of water was added, and the mixture was kneaded well to form a paste having a diameter of 0. After extruding through a 7 mm sieving hole and drying, it is cut into a length of 0.5 to 1 mm to obtain granules.

[0161]

INDUSTRIAL APPLICABILITY The compound of the present invention represented by the general formula [I] or [II] is an annual weed, such as Taenia japonicus, Pleurotus cornucopiae, and Kokonagi, which occur in paddy fields, and Urikawa, Omodaka,
It is also possible to control perennial weeds such as Mizugaya-tsuri, Kurogwai, Firefly, and Heramodeda. In addition, various weeds that are problematic in the field, for example, broad-leaved weeds such as Pteris chinensis, Aobiyu, Shiroza, Yaemgra, Chickweed, Ichibi, American stag deer, American hornwort, morning glory, Trifolium japonicum, Haesumedge, Yellow hemlock, Cyperus japonicus, Kogoyuga, Komegari. Perennial such as 1
It exerts an excellent herbicidal effect over a wide range of the pre-emergence and growing seasons of grass weeds such as annual Cyperaceae weeds, millet, crabgrass, green locusts, bluegrass, Johnsongrass, Nostaceae, wild oats.

On the other hand, the herbicide of the present invention is highly safe against crops, among which rice, wheat, barley, corn,
Highly safe against grain sorghum and sugar beet.

Next, the effects of the compound of the present invention will be described with reference to test examples. <Test Example 1> The paddy soil was filled in a plastic pot of herbicidal effect test 100 cm ² by paddy soil treatment, seeding each seed algebraic掻後, barnyardgrass (Ec), monochoria (Mo) and bulrush (Sc), depth It was flooded to 3 cm. The next day, the wettable powder prepared according to Formulation Example 1 was diluted with water and added dropwise to the water surface. The application rate was 100 g per 10 ares of the active ingredient. Then, it was grown in a greenhouse and 21 days after the treatment, the herbicidal effect was investigated according to the criteria in Table 4. The results are shown in Table 5.

[0164]

[Table 4]

[0165]

[Table 5]

[0166]

[Table 5] (continued)

[0167]

[Table 5] (continued)

[0168]

[Table 5] (continued)

[0169]

[Table 5] (continued)

[0170]

[Table 5] (continued)

<Test Example 2> Herbicidal effect test by treatment of upland soil 120 cm ² plastic pot was filled with upland soil,
Streaked pod (Po), Aubiyu (Am), Shiroza (C
h), various seeds of Kogomegayatsuri (Ci) were sown and covered with soil. A wettable powder prepared according to Formulation Example 1 is diluted with water,
A small sprayer uniformly sprayed 100 l per 10 are on the soil surface so that the active ingredient was 100 g per 10 are. Then, it was grown in a greenhouse, and the herbicidal effect was investigated on the 21st day of treatment according to the criteria in Table 4. The results are shown in Table 6.

[0172]

[Table 6]

[0173]

[Table 6] (continued)

[0174]

[Table 6] (continued)

[0175]

[Table 6] (continued)

[0176]

[Table 6] (continued)

[0177]

[Table 6] (continued)

[0178]

[Table 6] (continued)

<Test Example 3> Herbicidal effect test by foliar treatment of upland field A 120 cm ² plastic pot was filled with upland field soil,
Streaked pod (Po), Aubiyu (Am), Shiroza (C
h), after seeding various seeds of the Kogomegayatsuri (Ci) and growing them in a greenhouse for 2 weeks, the wettable powder prepared according to Formulation Example 1 is diluted with water so that the active ingredient becomes 100 g per 10 ares. 100 l per 10 ares was foliar-sprayed from above the plant body with a small sprayer. Then, it was grown in a greenhouse, and the herbicidal effect was investigated on the 14th day of treatment according to the criteria in Table 4. The results are shown in Table 7.

[0180]

[Table 7]

[0181]

[Table 7] (continued)

[0182]

[Table 7] (continued)

[0183]

[Table 7] (continued)

[0184]

[Table 7] (continued)

[0185]

[Table 7] (continued)

<Test Example 4> Crop Selectivity Test by Paddy Soil Treatment 100 cm ² plastic pots were filled with paddy soil,
After water entry and scratching, seeds of millet (Ec), eel (Mo) and firefly (Sc) are sown at a depth of 0.5 cm, and two paddy rice (Or) at the 2-leaf stage are transplanted at a depth of 2 cm and 2 It was transplanted and flooded to a water depth of 3 cm. On the next day, a predetermined amount of active ingredient (gai / 10a) of the wettable powder prepared according to Formulation Example 1 was diluted with water and the solution was dropped on the water surface. Then, the plants were grown in a greenhouse, and 28 days after the treatment, herbicidal effects and phytotoxicity were investigated according to the criteria shown in Table 4. The results are shown in Table 8.

[0187]

[Table 8]

[0188]

[Table 8] (continued)

[0189]

[Table 8] (continued)

<Test Example 5> Crop Selectivity Test by Upland Field Treatment 600 cm ² plastic pots were filled with upland field soil,
Wheat (Tr), corn (Ze), grain sorghum (Gs), giant sardine (Po), bluefin (A)
m), white chrysanthemum (Ch), velvetleaf (Ab), morning glory (Ip), lobster (Xa), and sprouts (CR) were sown and planted to cover soil. The next day, the prescribed amount of active ingredient (ga) of the wettable powder prepared according to Formulation Example 1 was determined.
i / 10a) was diluted with water, and 100 l per 10 are was evenly sprayed on the soil surface with a small sprayer. Then, it was grown in a greenhouse and 21 days after the treatment, the herbicidal effect was investigated according to the criteria in Table 4. The test results are shown in Table 9.

[0191]

[Table 9]

[0192]

[Table 9] (continued)

<Test Example 5> Crop selectivity test by foliar treatment of upland field A 600 cm ² plastic pot was filled with upland field soil,
Wheat (Tr), corn (Ze), grain sorghum (Gs), giant sardine (Po), bluefin (A)
m), chylosa (Ch), velvetleaf (Ab), morning glory (Ip), oriental fir tree (Xa), and sprouts of tuberous sedge (CR) and seeds, and after planting and covering with soil for 2 weeks, a formulation example A predetermined amount of active ingredient (gai / 10a) of the wettable powder prepared according to 1. was diluted with water, and 100 l per 10 are was sprayed on the whole plant from above the plant with a small sprayer. Then, it was grown in a greenhouse, and the herbicidal effect was investigated on the 14th day of treatment according to the criteria in Table 4. The results are shown in Table 10.

[0194]

[Table 10]

[0195]

[Table 10] (continued)

Front page continued (72) Inventor Masatoshi Tamaru Shiooka Prefecture Iwata-gun Fukuda-cho 1 408 Shioita Co., Ltd.KII Co., Ltd. (72) Inventor Masahito Inamori Shizuoka Iwata-gun Shioita 1 Kei Research Institute Co., Ltd. (72) Nobuo Takefuji Inventor Nobuo Shiota, Fukuda-cho, Iwata-gun, Shizuoka Prefecture 1 Kai Research Institute Co., Ltd. (72) Katsutada Yanagisawa Kamo Kikugawa-cho, Ogasa-gun, Shizuoka Prefecture Address 1809 (72) Inventor Yasunori Ogawa 58, 1138 Kakegawa, Kakegawa, Shizuoka Prefecture

Claims (6)

[Claims] 1. A general formula: {In the formula, R ¹ is a hydrogen atom, an alkyl group, a cycloalkyl group, a haloalkyl group, an alkoxyalkyl group, a benzyloxyalkyl group, a benzyl group, a phenyl group, a pyridyl group, a dialkylaminocarbonyl group, an alkoxycarbonyl group, an alkylsulfonyl group. , A phenylsulfonyl group, a dialkylaminosulfonyl group, a haloalkylcarbonyl group, an alkylcarbonyl group, a benzoyl group or an alkenyl group, R ² and R ³ are the same or different,
Hydrogen atom, halogen atom, alkyl group, cycloalkyl group, alkenyl group, alkoxycarbonylalkenyl group, alkynyl group, haloalkyl group, alkoxyalkyl group, alkoxycarbonylalkyl group, alkylcarbonylalkyl group, cycloalkylcarbonylalkyl group, cyanoalkyl group , A dialkylaminocarbonylalkyl group, a dialkylaminoalkyl group, a dialkylaminosulfonylalkyl group, an azidoalkyl group, a benzyl group, a phenyl group, a nitro group, a cyano group, an azido group, an amino group, a monoalkylamino group, a dialkylamino group,
A benzylamino group, an alkylcarbonylamino group which may be substituted with a halogen atom, a benzoylamino group, an alkoxycarbonylamino group, a phenoxycarbonylamino group, an alkylsulfonylamino group which may have an amino group substituted with an alkyl group, an amino group A phenylsulfonylamino group which may be substituted with an alkyl group, an alkylideneamino group, a benzylideneamino group, an optionally substituted tetrazolyl group, a formula —COR ⁴ (in the formula, R ⁴ is a hydrogen atom,
Hydroxyl group, alkyl group, cycloalkyl group, haloalkyl group, alkenyl group, alkynyl group, benzyl group, phenyl group, alkoxy group, haloalkoxy group, alkoxyalkoxy group, alkenyloxy group, haloalkenyloxy group, alkynyloxy group, benzyloxy Represents a group or a phenoxy group. ), A group represented by the formula: —C (O) NR ⁵
R ⁶ (wherein, ^{R 5} and ^{R 6} are the same or different and a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, a benzyl group, a phenyl group or an alkoxy group.), A group represented by the formula -SR ⁷ (In the formula, R ⁷ represents a hydrogen atom, an alkyl group or a haloalkyl group.), Formula -S
A group represented by O ₂ NR ⁵ R ⁶ (in the formula, R ⁵ and R ⁶ have the same meanings as described above), a formula —S (O) nR ⁸ (wherein n is an integer of 1 or 2). And R ⁸ represents an alkyl group, an alkenyl group, or a haloalkyl group), a group represented by the formula —OR ⁹ [wherein, R ⁹ represents a hydrogen atom, an alkyl group,
A cycloalkylalkyl group, an alkenyl group, an alkynyl group, a benzyl group (the group may be substituted with a halogen atom, an alkyl group or an alkoxy group), a haloalkyl group, a haloalkenyl group, a phenyl group (the group is a halogen atom, May be substituted with an alkyl group or an alkoxy group), an alkoxyalkyl group, an alkoxyalkoxyalkyl group, a haloalkoxyalkyl group, a benzyloxyalkyl group, a phenoxyalkyl group, an alkylthioalkyl group, a dialkylaminoalkyl group, an azidoalkyl group, Indicates an alkylcarbonyl group, haloalkylcarbonyl group, benzoyl group, dialkylaminocarbonyl group, cyanoalkyl group, alkylideneamino group, dialkylideneamino group, benzylideneamino group or alkoxycarbonylalkyl group. ] The group represented by or formula-C
(= NOR ¹⁰ ) R ¹¹ (wherein R ¹⁰ is a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, a benzyl group,
It represents a haloalkyl group or a phenyl group, and R ¹¹ represents a hydrogen atom, an alkyl group, a benzyl group, a haloalkyl group or a phenyl group. ), And R ² and R ³ may form a ring with an alkyl group which may contain a hetero atom. A
And B are the same or different and each represents an alkyl group, a haloalkyl group, an alkoxy group, a monoalkylamino group, a dialkylamino group, a halogen atom or a haloalkoxy group,
Z represents a methine group or a nitrogen atom, X represents an oxygen atom or a sulfur atom, and Y represents a hydrogen atom, an alkyl group or an alkoxyalkyl group. } The indazole sulfonyl urea derivative shown by these. 2. A general formula: (In the formula, R ¹ represents a hydrogen atom, an alkyl group or an alkenyl group, R ² and R ³ are the same or different, and a hydrogen atom,
Represents a halogen atom, an alkyl group, an alkoxy group, a haloalkoxy group, an alkylthio group, an alkylsulfinyl group, an alkylsulfonyl group, an alkoxycarbonyl group, a dialkylaminocarbonyl group, a nitro group or a cyano group, A and B are the same or different, An alkyl group, an alkoxy group or a halogen atom is shown, and Z is a methine group or a nitrogen atom. ) The indazole sulfonylurea derivative shown by these. 3. A general formula: (In the formula, R ¹ represents a hydrogen atom, an alkyl group or a phenyl group, R ² and R ³ are the same or different, and are a hydrogen atom, a halogen atom, an alkyl group, a hydroxyl group, an alkoxy group, a haloalkenyloxy group, an alkoxycarbonyl. Alkoxy group, cycloalkylalkoxy group, dialkylaminoalkoxy group, alkoxyalkoxy group, haloalkoxy group, alkynyloxy group, alkenyloxy group, alkylthio group, alkylsulfonyl group, alkoxycarbonyl group, dialkylaminocarbonyl group, nitro group, cyano group , A monoalkylamino group, a dialkylamino group or a benzylamino group, A and B are the same or different and each represents an alkyl group, an alkoxy group or a halogen atom, and Z represents a methine group or a nitrogen atom.). Indazole sulfoni Urea derivatives. 4. A general formula: {In the formula, R ¹ is a hydrogen atom, an alkyl group, a cycloalkyl group, a haloalkyl group, an alkoxyalkyl group, a benzyloxyalkyl group, a benzyl group, a phenyl group, a pyridyl group, a dialkylaminocarbonyl group, an alkoxycarbonyl group, an alkylsulfonyl group. , A phenylsulfonyl group, a dialkylaminosulfonyl group, a haloalkylcarbonyl group, an alkylcarbonyl group, a benzoyl group or an alkenyl group, R ² and R ³ are the same or different,
Hydrogen atom, halogen atom, alkyl group, cycloalkyl group, alkenyl group, alkoxycarbonylalkenyl group, alkynyl group, haloalkyl group, alkoxyalkyl group, alkoxycarbonylalkyl group, alkylcarbonylalkyl group, cycloalkylcarbonylalkyl group, cyanoalkyl group , A dialkylaminocarbonylalkyl group, a dialkylaminoalkyl group, a dialkylaminosulfonylalkyl group, an azidoalkyl group, a benzyl group, a phenyl group, a nitro group, a cyano group, an azido group, an amino group, a monoalkylamino group, a dialkylamino group,
A benzylamino group, an alkylcarbonylamino group which may be substituted with a halogen atom, a benzoylamino group, an alkoxycarbonylamino group, a phenoxycarbonylamino group, an alkylsulfonylamino group which may have an amino group substituted with an alkyl group, an amino group A phenylsulfonylamino group which may be substituted with an alkyl group, an alkylideneamino group, a benzylideneamino group, an optionally substituted tetrazolyl group, a formula —COR ⁴ (in the formula, R ⁴ is a hydrogen atom,
Hydroxyl group, alkyl group, cycloalkyl group, haloalkyl group, alkenyl group, alkynyl group, benzyl group, phenyl group, alkoxy group, haloalkoxy group, alkoxyalkoxy group, alkenyloxy group, haloalkenyloxy group, alkynyloxy group, benzyloxy Represents a group or a phenoxy group. ), A group represented by the formula: —C (O) NR ⁵
R ⁶ (wherein, ^{R 5} and ^{R 6} are the same or different and a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, a benzyl group, a phenyl group or an alkoxy group.), A group represented by the formula -SR ⁷ (In the formula, R ⁷ represents a hydrogen atom, an alkyl group or a haloalkyl group.), Formula -S
A group represented by O ₂ NR ⁵ R ⁶ (in the formula, R ⁵ and R ⁶ have the same meanings as described above), a formula —S (O) nR ⁸ (wherein n is an integer of 1 or 2). And R ⁸ represents an alkyl group, an alkenyl group, or a haloalkyl group), a group represented by the formula —OR ⁹ [wherein, R ⁹ represents a hydrogen atom, an alkyl group,
A cycloalkylalkyl group, an alkenyl group, an alkynyl group, a benzyl group (the group may be substituted with a halogen atom, an alkyl group or an alkoxy group), a haloalkyl group, a haloalkenyl group, a phenyl group (the group is a halogen atom, May be substituted with an alkyl group or an alkoxy group), an alkoxyalkyl group, an alkoxyalkoxyalkyl group, a haloalkoxyalkyl group, a benzyloxyalkyl group, a phenoxyalkyl group, an alkylthioalkyl group, a dialkylaminoalkyl group, an azidoalkyl group, Indicates an alkylcarbonyl group, haloalkylcarbonyl group, benzoyl group, dialkylaminocarbonyl group, cyanoalkyl group, alkylideneamino group, dialkylideneamino group, benzylideneamino group or alkoxycarbonylalkyl group. ] The group represented by or formula-C
(= NOR ¹⁰ ) R ¹¹ (wherein R ¹⁰ is a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, a benzyl group,
It represents a haloalkyl group or a phenyl group, and R ¹¹ represents a hydrogen atom, an alkyl group, a benzyl group, a haloalkyl group or a phenyl group. ), And R ² and R ³ may form a ring with an alkyl group which may contain a hetero atom. }
An indazole sulfonamide derivative represented by. 5. A general formula: {In the formula, R ¹ is a hydrogen atom, an alkyl group, a cycloalkyl group, a haloalkyl group, an alkoxyalkyl group, a benzyloxyalkyl group, a benzyl group, a phenyl group, a pyridyl group, a dialkylaminocarbonyl group, an alkoxycarbonyl group, an alkylsulfonyl group. , A phenylsulfonyl group, a dialkylaminosulfonyl group, a haloalkylcarbonyl group, an alkylcarbonyl group, a benzoyl group or an alkenyl group, R ² and R ³ are the same or different,
Hydrogen atom, halogen atom, alkyl group, cycloalkyl group, alkenyl group, alkoxycarbonylalkenyl group, alkynyl group, haloalkyl group, alkoxyalkyl group, alkoxycarbonylalkyl group, alkylcarbonylalkyl group, cycloalkylcarbonylalkyl group, cyanoalkyl group , A dialkylaminocarbonylalkyl group, a dialkylaminoalkyl group, a dialkylaminosulfonylalkyl group, an azidoalkyl group, a benzyl group, a phenyl group, a nitro group, a cyano group, an azido group, an amino group, a monoalkylamino group, a dialkylamino group,
A benzylamino group, an alkylcarbonylamino group which may be substituted with a halogen atom, a benzoylamino group, an alkoxycarbonylamino group, a phenoxycarbonylamino group, an alkylsulfonylamino group which may have an amino group substituted with an alkyl group, an amino group A phenylsulfonylamino group which may be substituted with an alkyl group, an alkylideneamino group, a benzylideneamino group, an optionally substituted tetrazolyl group, a formula —COR ⁴ (in the formula, R ⁴ is a hydrogen atom,
Hydroxyl group, alkyl group, cycloalkyl group, haloalkyl group, alkenyl group, alkynyl group, benzyl group, phenyl group, alkoxy group, haloalkoxy group, alkoxyalkoxy group, alkenyloxy group, haloalkenyloxy group, alkynyloxy group, benzyloxy Group or phenyloxy group. ), A group represented by the formula: —C (O) N
R ⁵ R ⁶ (In the formula, R ⁵ and R ⁶ are the same or different and are a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group,
A benzyl group, a phenyl group or an alkoxy group is shown. ), A group represented by the formula: —SR ⁷ (in the formula, R ⁷ represents a hydrogen atom, an alkyl group or a haloalkyl group), and a group represented by the formula: —SO ₂ NR ⁵ R ⁶ (in the formula, R ⁵ And R ⁶ have the same meanings as described above.), A group represented by the formula —S (O) nR.
⁸ (In the formula, n represents an integer of 1 or 2, and R ⁸ represents an alkyl group, an alkenyl group, or a haloalkyl group.), Formula —OR ⁹ [In the formula, R ⁹ is a hydrogen atom, An alkyl group, a cycloalkylalkyl group, an alkenyl group, an alkynyl group, a benzyl group (the group may be substituted with a halogen atom, an alkyl group or an alkoxy group), a haloalkyl group, a haloalkenyl group, a phenyl group (the group is It may be substituted with a halogen atom, an alkyl group or an alkoxy group), an alkoxyalkyl group, an alkoxyalkoxyalkyl group, a haloalkoxyalkyl group, a benzyloxyalkyl group, a phenoxyalkyl group, an alkylthioalkyl group, a dialkylaminoalkyl group, an azide. Alkyl group, alkylcarbonyl group, haloalkylcarbonyl group, benzoyl Shows dialkylaminocarbonyl group, a cyanoalkyl group, alkylidene group, di alkylideneamino group, a benzylideneamino group or an alkoxycarbonylalkyl group. ] The group represented by or formula-C
(= NOR ¹⁰ ) R ¹¹ (wherein R ¹⁰ is a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, a benzyl group,
It represents a haloalkyl group or a phenyl group, and R ¹¹ represents a hydrogen atom, an alkyl group, a benzyl group, a haloalkyl group or a phenyl group. ), And R ² and R ³ may form a ring with an alkyl group which may contain a hetero atom. }
An indazole sulfonamide derivative represented by. 6. A herbicide containing the indazolesulfonylurea according to claim 1 as an active ingredient.