JPH101478A - Indazole sulfonylurea derivatives and herbicides - Google Patents

Abstract

(57) [Object] To provide an indazole sulfonylurea derivative which shows high safety specifically for beet which is a useful crop, and also has an excellent herbicidal effect on harmful weeds. SOLUTION: The general formula [I] [Wherein, R ¹ represents a haloalkylsulfonyl group, an alkenylsulfonyl group, a phenylcarbonyl group, a phenylsulfonyl group, or the like, and R ² and R ³ are the same or different and are a hydrogen atom, a halogen atom, an alkyl group, an alkoxycarbonyl group or A and B are the same or different, each represents an alkoxy group or an alkyl group, X represents an oxygen atom or a sulfur atom, Y represents a hydrogen atom or an alkyl group, and Z represents a nitrogen atom or Shows a methine group. ] And a herbicide containing the indazole sulfonylurea derivative as an active ingredient.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

The present invention relates to a novel indazole sulfonylurea derivative (hereinafter referred to as the compound of the present invention).
And a herbicide containing the same as an active ingredient.

[0002]

2. Description of the Related Art A number of sulfonylurea derivatives have been known as herbicides. That is, an indazole-4-sulfonylurea derivative is disclosed in JP-A-4-95091.
No., the disclosure of which is incorporated herein by reference. Indazole-3
-Sulfonylurea derivatives are disclosed in WO-950509. However, there is no description showing that the compound of the present invention specifically shows high safety to beet and at the same time exhibits an excellent herbicidal effect.

[0003]

SUMMARY OF THE INVENTION There is a need for weeds that exhibit high safety against useful crops and at the same time have an excellent herbicidal effect on harmful weeds.

[0004]

As a result of various studies, the present inventors have found that the compound of the present invention is an excellent herbicide having a high activity, and have completed the present invention.

That is, the present invention provides a compound represented by the general formula [I]:

[0006]

Embedded image In the formula, R ¹ is a haloalkylsulfonyl group, an alkenylsulfonyl group (the group may be substituted with a halogen atom), an alkynylsulfonyl group (the group may be substituted with a halogen atom), and a compound of the formula —COR ^12. [Wherein, R ¹²
Is a phenyl group (the group is substituted by a halogen atom, an alkyl group, a haloalkyl group, an alkoxy group, a haloalkoxy group, a nitro group or an alkoxycarbonyl group) or a heteroaromatic ring group (the group is a halogen atom, an alkyl group ,
It may be substituted by a haloalkyl group, an alkoxy group, a haloalkoxy group, a nitro group or an alkoxycarbonyl group. ). Or a group represented by the formula —SO ₂ R
¹² (wherein, R ¹² has the same meaning as described above), and R ² and R ³ are the same or different and are a hydrogen atom, a halogen atom, an alkyl group, a cycloalkyl group, an alkenyl Group, alkynyl group, haloalkyl group, alkoxyalkyl group, alkoxycarbonylalkyl group, alkylcarbonylalkyl group, cycloalkylcarbonylalkyl group, cyanoalkyl group, dialkylaminocarbonylalkyl group, dialkylaminoalkyl group, dialkylaminosulfonylalkyl group, azide Alkyl group, benzyl group, phenyl group, nitro group, cyano group, azide group, amino group, monoalkylamino group, dialkylamino group, benzylamino group, alkylcarbonylamino group optionally substituted by halogen atom, benzoylamino group , Arco Xycarbonylamino group, phenoxycarbonylamino group, alkylsulfonylamino group in which the amino group may be substituted with an alkyl group, phenylsulfonylamino group in which the amino group may be substituted with an alkyl group, alkylideneamino group, benzylideneamino group, An optionally substituted tetrazolyl group, formula -COR ⁴ (wherein
R ⁴ is a hydrogen atom, a hydroxyl group, an alkyl group, a cycloalkyl group, a haloalkyl group, an alkenyl group, an alkynyl group, a benzyl group, a phenyl group, an alkoxy group, a haloalkoxy group, an alkoxyalkoxy group, an alkenyloxy group, a haloalkenyloxy group, It represents an alkynyloxy group, a benzyloxy 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, phenyl or alkoxy group, wherein -SR ⁷ (wherein represented by a group.), ^{R 7} is a hydrogen atom, an alkyl group or a haloalkyl group.), a group represented by the formula -SO2NR ⁵ R ⁶ (wherein, R ⁵ and R ⁶
Has the same meaning as described above. ), A group represented by the formula -S
(O) a group represented by nR ⁸ (wherein R ⁸ represents an alkyl group, an alkenyl group or a haloalkyl group, and n represents an integer of 1 or 2), a formula —OR ⁹ [in the formula, 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, and a phenyl group (The group 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 dialkylamino Alkyl group, azidoalkyl group, alkylcarbonyl group, haloalkylcarbonyl group, Nzoiru group, a dialkylamino group, a cyano group, alkylidene group, di alkylideneamino group, a benzylideneamino group or an alkoxycarbonylalkyl group. Or a group represented by the formula —C (＝ NOR ¹⁰ ) R ¹¹ (wherein R
¹⁰ represents a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, a benzyl group, 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 optionally containing a hetero atom. A and B are the same or different and represent 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, and X represents an oxygen atom Or Y represents a hydrogen atom, an alkyl group or an alkoxyalkyl group. An indazole sulfonylurea derivative represented by｝.
And a herbicide containing the same as an active ingredient.

[0007] The terms used in this specification are defined below. The alkyl group means a linear or branched alkyl group having 1 to 30 carbon atoms, for example, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-
Butyl, isobutyl, sec-butyl, t-butyl, n-pentyl, isoamyl, neopentyl, n-hexyl, isohexyl, 3,3-dimethylbutyl, n-heptyl, 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, n-heptadecyl group, n-octadecyl group, n-nonadecyl group, n-eicosyl group and the like.

A group - [0008] alkoxy groups, each alkyl moiety and the alkyl sulfonyl group have the meanings given above (alkyl) -O- group, (alkyl) -SO _2.

The halogen atom includes fluorine, chlorine, bromine and iodine atoms.

A haloalkyl group is the same or different
Carbon atoms substituted with 10 to 10 halogen atoms
It means 10 linear or branched alkyl groups, and includes, for example, a chloromethyl group, a difluoromethyl group, a trifluoromethyl group, a 2,2,2-trifluoroethyl group and the like.

The alkenyl group means a linear or branched alkenyl group having 2 to 20 carbon atoms, for example, a vinyl group,
Allyl, isopropenyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, 3-
It includes a methyl-1-butenyl group, a 4-methyl-1-pentenyl group and the like.

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

The term "heteroaromatic group" means a 5- or 6-membered aromatic ring group containing from 1 to 4 nitrogen, oxygen or sulfur atoms and a condensed ring thereof with a benzene ring.
Examples thereof include a furyl group, a thienyl group, a pyrazolyl group, an imidazolyl group, a benzofuranyl group, a benzothiazolyl group, a pyridyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a quinolyl group, and a quinoxalinyl group.

In the general formula [I], as a group of compounds exhibiting a preferable herbicidal effect, R ¹ is a chloromethylsulfonyl group or a benzoyl group (the group is a halogen atom, an alkyl group, a haloalkyl group, an alkoxy group, a nitro group). R ² is a group represented by the formula —COOR ¹³ (wherein R ¹³ represents an alkyl group having 1 to 3 carbon atoms), and R ³ is a hydrogen atom Yes, A
And B are the same or different and each represents 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.

[0015]

BEST MODE FOR CARRYING OUT THE INVENTION Next, Tables 1 to 27 show typical examples of the compound of the present invention represented by the general formula [I], but are not limited thereto. The compound numbers will be referred to in the following description.

In the compound represented by the general formula [I],
A compound having an alkenylsulfonyl group for R ¹ has C =
Due to the presence of the C bond, there are two types of geometric isomers, ie, the entgegen (E) -form and the tuzamen (Z) -form, but the present invention relates to any of these isomers and a mixture of these isomers in any ratio. Is also included.

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

Me: methyl group, Et: ethyl group, Pr: propyl group, Pr-i: isopropyl group, Bu: butyl group, Bu-i: isobutyl group, Bu-sec: sec-butyl group, Bu-t: tert-butyl group, Pen: n-pentyl group, Bn: benzyl group, Ph: phenyl group,

[0019]

[Table 1]

[0020]

[Table 2]

[0021]

[Table 3]

[0022]

[Table 4]

[0023]

[Table 5]

[0024]

[Table 6]

[0025]

[Table 7]

[0026]

[Table 8]

[0027]

[Table 9]

[0028]

[Table 10]

[0029]

[Table 11]

[0030]

[Table 12]

[0031]

[Table 13]

[0032]

[Table 14]

[0033]

[Table 15]

[0034]

[Table 16]

[0035]

[Table 17]

[0036]

[Table 18]

[0037]

[Table 19]

[0038]

[Table 20]

[0039]

[Table 21]

[0040]

[Table 22]

[0041]

[Table 23]

[0042]

[Table 24]

[0043]

[Table 25]

[0044]

[Table 26]

[0045]

[Table 27]

The compound of the present invention represented by the general formula [I] is
For example, it can be manufactured according to the following manufacturing method 1, but is not limited to these methods. <Production method 1>

[0047]

Embedded image (In the formula, R ¹ , R ² , R ³ , A, B, Z, X, and Y have the same meaning as described above, and L represents a halogen atom.)

That is, the compound [I] of the present invention comprises an intermediate for the production of the compound of the present invention represented by the general formula [Ia] (the production method will be described later, hereinafter referred to as an intermediate) and a compound of the general formula [II] It can be produced by reacting the compound shown.

This reaction is usually carried out in a solvent or in the absence of a solvent, if necessary, in the presence of a base. The reaction temperature ranges from -20 ° C. to the boiling point of the solvent, and the reaction time ranges from 0.5 hour to 0.5 hour. The range is 24 hours. The amount of the compound to be subjected to the reaction is 1 to 2 equivalents of the compound represented by the general formula [II] and the amount of the base independently with respect to 1 equivalent of the raw material represented by the general formula [Ia].

Examples of the solvent include 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; esters such as ethyl acetate and butyl acetate; nitro compounds such as nitromethane and nitrobenzene; nitriles such as acetonitrile and isobutyronitrile; N, N-dimethylformamide (DMF ), N,
N-dimethylacetamide (DMAC), dimethylsulfoxide (DMSO), N-methylpyridone (NM
Aprotic polar solvents such as P) 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-
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. If necessary, a catalyst such as 4- (N, N-dimethylamino) pyridine can be used.

The intermediate represented by the general formula [Ia] can be produced by the method disclosed in WO-9500509.

[0053]

The production method, the preparation method and the use of the compound of the present invention will be specifically described below with reference to examples. The production method of the intermediate is described as a reference example.

Production Example 1 Methyl 1-chloromethanesulfonyl-3-{[(4,6-dimethoxy-2-pyrimidinyl) aminocarbonyl] aminosulfonyl} -1H-
Indazole-4-carboxylate (Compound No. I-
31) Preparation of methyl 3-{[(4,6-dimethoxy-2-pyrimidinyl) aminocarbonyl] aminosulfonyl} -1H-
1.5 g of indazole-4-carboxylate (3.4
mmol) in acetonitrile (20 ml), and 0.7 g (6.93 mmol) of triethylamine was added to the solution at 10 ° C.
And 0.77 g of chloromethanesulfonyl chloride (5.
16 mmol) was added. After stirring at room temperature for 2 hours, the mixture was added to water and extracted with ethyl acetate. After washing the ethyl acetate with water, drying and concentration, the residue was crystallized by adding ether, and the desired methyl 1-chloromethanesulfonyl-3-
{[(4,6-dimethoxy-2-pyrimidinyl) aminosulfonyl} aminosulfonyl) -1H-indazole-4-carboxylate (1.2 g, mp 177-17)
9 ° C., yield 63.6%). ¹ H-NMR data (60 MHz, CDCl ₃ / DMS
O-d ₆ solvent, δ value) 3.93 (3H, s) 3.96 (6H, s) 5.5 (2H, s) 5.83 (1H, s) 7.73-8.43 (3H) , M) 10.5 (1H, s) 13.96 (1H, br)

Production Example 2 Methyl 1-allylsulfonyl-3-{[(4,6-dimethoxy-2-pyrimidinyl)
Aminocarbonyl] aminosulfonyl} -1H-indazole-4-carboxylate (Compound No. I-31
Preparation of 3) Methyl 3-{[(4,6-dimethoxy-2-pyrimidinyl) aminocarbonyl] aminosulfonyl} -1H-
1.5 g of indazole-4-carboxylate (3.4
mmol), 0.7 g of triethylamine (6.93 mm
ol), 0.72 g of allylsulfonyl chloride (5.
12 mmol) in acetonitrile in the same manner as in Production Example 1 to give the desired methyl 1-allylsulfonyl-3-
{[(4,6-Dimethoxy-2-pyrimidinyl) aminocarbonyl] aminosulfonyl} -1H-indazole-4-carboxylate (1.3 g, mp 177-17)
9 ° C., yield 70.7%). ¹ H-NMR data (60 MHz, CDCl ₃ / DMS
_{O-d 6} solvent, [delta] values) 3.9 (3H, s) 3.93 (6H, s) 4.22 (2H, d) 4.82~5.52 (3H, m) 5.8 (1H , S) 7.5-8.4 (3H, m) 10.46 (1H, br) 13.13 (1H, br)

Reference Example Methyl 3-{[(4,6-dimethoxy-2-pyrimidinyl) aminocarbonyl] aminosulfonyl} -1H-
Preparation of indazole-4-carboxylate Methyl 3-aminosulfonyl-1H-indazole-
9.9 g (38.8 mmol) of 4-carboxylate,
To a solution of 10.9 g (39.6 mmol) of phenyl (4,6-dimethoxypyrimidin-2-yl) carbamate in acetonitrile (100 ml) was added 12.1 g of DBU.
(79.2 mmol) and the mixture was stirred at room temperature for 2 hours. The mixture was poured into ice water, acidified with citric acid, and the resulting crystals were collected by filtration, washed successively with water, isopropyl ether and ether, and then 14.1 g of the desired product (colorless needle crystals) (yield: 8).
3.4%). Melting point: 179-180 ° C ¹ H-NMR data (300 MHz, CDCl ₃ / DM
SO-d ₆ solvent, δ value) 3.93 (3H, s) 4.05 (6H, s) 5.81 (1H, s) 7.40 to 7.82 (3H, m) 9.25 (1H) , Br) 12.82 (1H, br) 13.72 (1H, br)

The herbicide of the present invention comprises an indazole sulfonylurea derivative represented by the general formula [I] as an active ingredient.

In order to use the compound of the present invention as a herbicide, the compound of the present invention itself may be used. However, a carrier, a surfactant, a dispersant, an auxiliary agent or the like generally used for formulation may be blended. , Powders, wettable powders, emulsions, fine granules or granules, and the like.

The carriers used in the formulation are as follows:
Examples thereof include solid carriers such as talc, bentonite, clay, 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 alkyl benzene sulfonate, metal dinaphthyl methanedisulfonate, alcohol sulfate, alkyl aryl sulfonate, lignin sulfonate, polyoxyethylene glycol ether, and polyoxyethylene glycol ether. Oxyethylene alkyl aryl ether, polyoxyethylene sorbitan monoalkylate and the like can be mentioned. Examples of the adjuvant include carboxymethyl cellulose, polyethylene glycol, gum arabic and the like. When used, they are diluted to an appropriate concentration and sprayed or applied directly.

The herbicide of the present invention can be used by foliage application, soil application or surface application. The compounding ratio of the active ingredient is appropriately selected as necessary, but when it is a powder or granule, it is appropriately selected from the range of 0.01 to 10% (weight), preferably 0.05 to 5% (weight). Is good. 1 to 50% when used as emulsion and wettable powder
(Weight), preferably from 5 to 30% (weight).

The application rate of the herbicide of the present invention varies depending on the kind of the compound used, the target weed, the tendency to emerge, the environmental conditions, the dosage form used, and the like. 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. Further, when used in a liquid form such as an emulsion and a wettable powder, 0.1 to 50,000 p.
pm, preferably in the range of 10 to 10,000 ppm.

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

Next, the preparation method will be specifically described with reference to typical preparation 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, “parts” means parts by weight.

Formulation Example 1 Wettable powder 0.5 parts of polyoxyethylene octylphenyl ether, 0.5 parts of sodium salt of β-naphthalenesulfonic acid formalin condensate, 10 parts of compound (I-31), diatomaceous earth Are mixed and pulverized to obtain a wettable powder.

<Formulation Example 2> Water-dispersible agent 10 parts of compound (I-37), 0.5 parts of polyoxyethylene octylphenyl ether, 0.5 parts of sodium salt of β-naphthalenesulfonic acid formalin condensate, diatomaceous earth And 5 parts of white carbon and 64 parts of clay are mixed and pulverized to obtain a wettable powder.

<Formulation Example 3> Water-dispersible compound 10 parts of compound (I-61), 0.5 parts of polyoxyethylene octylphenyl ether, 0.5 parts of sodium salt of β-naphthalenesulfonic acid formalin condensate, diatomaceous earth And 5 parts of white carbon and 64 parts of calcium carbonate are mixed and pulverized to obtain a wettable powder.

Formulation Example 4 Emulsion 30 parts of compound (I-151), 60 parts of an equal mixture of xylene and isophorone, surfactant polyoxyethylene sorbitan alkylate, polyoxyethylene alkylaryl polymer and alkylaryl sulfonate An emulsion is obtained by adding 10 parts of the mixture and stirring them well.

Formulation Example 5 Granules 10 parts of compound (I-211), 80 parts of a bulking agent obtained by mixing talc and bentonite at a ratio of 1: 3, 5 parts of white carbon, surfactant polyoxyethylene 10 parts of water was added to 5 parts of a mixture of sorbitan alkylate, polyoxyethylene alkylaryl polymer and alkylarylsulfonate, and the mixture was kneaded well and extruded through a sieve having a diameter of 0.7 mm, dried and dried. Cut to a length of 5 to 1 mm to obtain granules.

Next, the effects of the compound of the present invention will be described with reference to Test Examples. In the test, the following compounds described in WO9505099 were used as comparative drugs.

Comparative drug: 4-chloro-1-methanesulfonyl-3-{[(4,6-dimethoxy-2-pyrimidinyl) aminocarbonyl] aminosulfonyl} -1H-indazole (described in Compound No. I-626)

<Test Example 1> Beet selectivity test by upland field foliar treatment A 600 cm2 plastic pot was filled with upland soil.
Beet (Be), chickweed (St), dog chamomile (M
a) seeds were sown and grown for 2 weeks in a greenhouse, and then the prescribed active ingredient amount (25 ga) of the wettable powder prepared according to Formulation Example 1
i / ha) was diluted with water, and 1000 l per hectare was sprayed with foliage from above the whole plant using a small sprayer. Thereafter, the plants were grown in a greenhouse, and on the 14th day of the treatment, the herbicidal effect was investigated according to the criteria in Table 28. Table 29 shows the results.
It was shown to.

[0073]

[Table 28]

[0074]

[Table 29]

[0075]

Industrial Applicability The compound of the present invention represented by the general formula [I] can be used as a variety of weeds which are problematic as beet herbicides in upland fields, for example, A. aphidum, Aobuyu, Shiroza, Ichibi,
American sika deer, dogwood, Korean morning glory, American horned frog, ibis grass, morning glory,
In addition to broadleaf weeds such as Onami fir, purslane, ragweed, chickweed, yamgra, violet, pufferfish, stalk beetle, buckwheat, honeywort, dokuninjin, yamayama, dog chamomile, etc. It exerts an excellent herbicidal effect over a wide range from the pre-emergence to the growing season of grass weeds such as cyperaceous weeds, barnyardgrass, crabgrass, scrophulariformes, scrophularis, johnsongrass, rosacea, wild oats and the like. The herbicides of the present invention show high safety against beets.

──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. ⁶ Identification code Agency reference number FI Technical display location C07D 231: 56 239: 42) (C07D 403/12 231: 56 239: 52) (C07D 403/12) (23:56 251: 46) (C07D 403/12 231: 56 251: 14) (C07D 401/14 213: 81 231: 56 239: 52) (C07D 409/14 231: 56 239: 52 333: 38) ( 72) Inventor Masatoshi Tamaru 408-1, Shioda, Fukuda-cho, Iwata-gun, Shizuoka Prefecture Inside the KI Research Institute Co., Ltd. (72) Inventor Ryo Hanai 2-4, Aobadai, Kikugawa-cho, Ogasa-gun, Shizuoka Prefecture 9 (72) Invention Person Souta Uozu 3353 Kamo, Kikugawa-cho, Ogasa-gun, Shizuoka Prefecture (72) Inventor Mitsuhiro Yamachi 1809, Kamo, Kikukawa-cho, Ogasa-gun, Shizuoka Prefecture (72) Inventor Hideo Sadohara 2-9-9 Horinouchi, Niiza City, Saitama Prefecture

Claims (7)

[Claims] 1. A compound of the general formula [I] In the formula, R ¹ is a haloalkylsulfonyl group, an alkenylsulfonyl group (the group may be substituted with a halogen atom), an alkynylsulfonyl group (the group may be substituted with a halogen atom), and a compound of the formula —COR ^12. [Wherein, R ¹²
Is a phenyl group (the group is substituted by a halogen atom, an alkyl group, a haloalkyl group, an alkoxy group, a haloalkoxy group, a nitro group or an alkoxycarbonyl group) or a heteroaromatic ring group (the group is a halogen atom, an alkyl group ,
It may be substituted by a haloalkyl group, an alkoxy group, a haloalkoxy group, a nitro group or an alkoxycarbonyl group. ). Or a group represented by the formula —SO ₂ R
¹² (wherein, R ¹² has the same meaning as described above), and R ² and R ³ are the same or different and are a hydrogen atom, a halogen atom, an alkyl group, a cycloalkyl group, an alkenyl Group, alkynyl group, haloalkyl group, alkoxyalkyl group, alkoxycarbonylalkyl group, alkylcarbonylalkyl group, cycloalkylcarbonylalkyl group, cyanoalkyl group, dialkylaminocarbonylalkyl group, dialkylaminoalkyl group, dialkylaminosulfonylalkyl group, azide Alkyl group, benzyl group, phenyl group, nitro group, cyano group, azide group, amino group, monoalkylamino group, dialkylamino group, benzylamino group, alkylcarbonylamino group optionally substituted by halogen atom, benzoylamino group , Arco Xycarbonylamino group, phenoxycarbonylamino group, alkylsulfonylamino group in which the amino group may be substituted with an alkyl group, phenylsulfonylamino group in which the amino group may be substituted with an alkyl group, alkylideneamino group, benzylideneamino group, An optionally substituted tetrazolyl group, formula -COR ⁴ (wherein
R ⁴ is a hydrogen atom, a hydroxyl group, an alkyl group, a cycloalkyl group, a haloalkyl group, an alkenyl group, an alkynyl group, a benzyl group, a phenyl group, an alkoxy group, a haloalkoxy group, an alkoxyalkoxy group, an alkenyloxy group, a haloalkenyloxy group, It represents an alkynyloxy group, a benzyloxy 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, phenyl or alkoxy group, wherein -SR ⁷ (wherein represented by a group.), ^{R 7} is a hydrogen atom, an alkyl group or a haloalkyl group.), a group represented by the formula -SO2NR ⁵ R ⁶ (wherein, R ⁵ and R ⁶
Has the same meaning as described above. ), A group represented by the formula -S
(O) a group represented by nR ⁸ (wherein R ⁸ represents an alkyl group, an alkenyl group or a haloalkyl group, and n represents an integer of 1 or 2), a formula —OR ⁹ [in the formula, 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, and a phenyl group (The group 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 dialkylamino Alkyl group, azidoalkyl group, alkylcarbonyl group, haloalkylcarbonyl group, Nzoiru group, a dialkylamino group, a cyano group, alkylidene group, di alkylideneamino group, a benzylideneamino group or an alkoxycarbonylalkyl group. Or a group represented by the formula —C (＝ NOR ¹⁰ ) R ¹¹ (wherein R
¹⁰ represents a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, a benzyl group, 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 optionally containing a hetero atom. A and B are the same or different and represent 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, and X represents an oxygen atom Or Y represents a hydrogen atom, an alkyl group or an alkoxyalkyl group. An indazole sulfonylurea derivative represented by｝. 2. In the general formula [I], R ¹ is a haloalkylsulfonyl group, an alkenylsulfonyl group (the group may be substituted by a halogen atom) or an alkynylsulfonyl group (the group may be substituted by a halogen atom). A benzoyl group (the group is substituted with a halogen atom, an alkyl group, a haloalkyl group, an alkoxy group, a haloalkoxy group, a nitro group or an alkoxycarbonyl group), a benzenesulfonyl group (the group is a halogen atom, Alkyl group,
It is substituted by a haloalkyl group, an alkoxy group, a haloalkoxy group, a nitro group or an alkoxycarbonyl group. And R ² and R ³ are the same or different and each represents a hydrogen atom, 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, Z is a methine group or a nitrogen atom, and X is an oxygen atom or a sulfur atom And Y
The indazole sulfonylurea derivative according to claim 1, wherein is a hydrogen atom, an alkyl group or an alkoxyalkyl group. 3. In the general formula [I], R ¹ is a haloalkylsulfonyl group, R ² and R ³ are the same or different, and are a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, a haloalkoxy group, an alkylthio group, Alkylsulfinyl group, alkylsulfonyl group, alkoxycarbonyl group, dialkylaminocarbonyl group, nitro group or cyano group, A and B are the same or different, alkyl group, alkoxy group or halogen atom, Z is methine group or The indazole sulfonylurea derivative according to claim 1, wherein the nitrogen atom, X is an oxygen atom or a sulfur atom, and Y is a hydrogen atom, an alkyl group or an alkoxyalkyl group. 4. In the general formula [I], R ¹ is a benzoyl group (this group is a halogen atom, an alkyl group, a haloalkyl group,
It is substituted by an alkoxy group, a haloalkoxy group, a nitro group, or an alkoxycarbonyl group. And R ² and R ³ are the same or different and each represents a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, a haloalkoxy group, an alkylthio group, an alkylsulfinyl group, an alkylsulfonyl group, an alkoxycarbonyl group, or a dialkylaminocarbonyl group. , A nitro group or a cyano group, A and B are the same or different and are an alkyl group, an alkoxy group or a halogen atom, Z is a methine group or a nitrogen atom, X is an oxygen atom or a sulfur atom, and Y is The indazole sulfonylurea derivative according to claim 1, wherein is a hydrogen atom, an alkyl group or an alkoxyalkyl group. 5. In the general formula [I], R ¹ is a chloromethylsulfonyl group, and R ² is a group represented by the formula —COOR ¹³ (wherein
R ¹³ represents an alkyl group having 1 to 3 carbon atoms. Wherein R ³ is a hydrogen atom, A and B are methoxy groups, Z is a methine group, X is an oxygen atom, and Y is a hydrogen atom. Indazole sulfonylurea derivatives of 6. In the general formula [I], R ¹ is a benzoyl group (this group is a halogen atom, an alkyl group, a haloalkyl group,
It is substituted with an alkoxy group or a nitro group. )
R ² is a group represented by the formula —COOR ¹³ (wherein, R ¹³ has the same meaning as described above), R ³ is a hydrogen atom, A and B are methoxy groups, and Z is 2. A methine group, X is an oxygen atom, and Y is a hydrogen atom.
The indazole sulfonylurea derivative of the above. 7. A herbicide comprising the indazole sulfonylurea derivative according to claim 1 as an active ingredient.