JP2016079121A - Heteroaryl sulfonamide compound and herbicide comprising the same - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a new herbicide exhibiting significant herbicidal activity against undesirable plants.SOLUTION: There is provided a heteroaryl sulfonamide compound represented by the formula (I) or a salt thereof. [Q represents a specific thiophene ring; Rto Reach independently represents H or C-Calkyl; T represents halogen or C-Calkyl; W represents O or S; X represents -O-Y, -S-Z, -SO-Zor -SO-Z; Y represents substituted C-Calkyl or substituted C-Calkylcarbonyl; Zrepresents H, hydroxyalkyl C-Calkyl or C-Calkoxy C-Calkyl; Zrepresents hydroxyalkyl C-Calkoxy or C-Calkoxy C-Calkyl; m represents an integer of 0 to 2; and n represents an integer of 0 to 5.]SELECTED DRAWING: None

Description

  The present invention relates to a heteroarylsulfonamide compound or a salt thereof, and more specifically, a novel heteroarylsulfonamide compound or salt thereof useful as an active ingredient of a herbicide, and a herbicide containing them. About.

  The following Patent Document 1, Patent Document 2 and Patent Document 3 disclose haloalkylsulfonanilide derivatives having a certain chemical structure. However, these patent documents do not disclose heteroarylsulfonamide compounds represented by the general formula (I) described later.

International Publication No. “WO2010 / 026989” International Publication Gazette “WO2010 / 119906” International Publication Gazette “WO2013 / 061973”

  Conventionally, there has been a demand for a herbicide that has excellent herbicidal performance against weeds and has safety for cultivated crops in order to save labor in controlling weeds and improve productivity of agricultural and horticultural crops. Yes. In the development of new herbicides in the future, there is a demand for the creation of compounds that can exhibit the desired herbicidal effect while keeping the amount of applied herbage low. In addition, compounds that have practical residual effects but are less likely to remain in the soil than necessary or have a negative impact on the environment due to the outflow of active ingredients to soils other than the application site due to rainwater, etc. Creation of is demanded. Furthermore, creation of a compound with high animal safety is desired. However, the search for new compounds suitable for such purposes relies on trial and error.

The inventors of the present invention have made various studies to find a better herbicide that can solve the above-described problems. As a result, the present inventors have found that a novel heteroarylsulfonamide compound exhibits a high herbicidal effect at a low dose in various weeds and also exhibits high safety in various useful crops, thereby completing the present invention.
That is, the present invention relates to the general formula (I)

[Where Q is the general formula (Q-1) or general formula (Q-2):

A thiophene ring represented by:
R ¹ is haloC ₁ -C ₆ alkyl;
R ² is a hydrogen atom, C ₁ -C ₆ alkyl, halo C ₁ -C ₆ alkyl, C ₃ -C ₆ alkenyl, C ₃ -C ₆ alkynyl, C ₁ -C ₆ alkoxy C ₁ -C ₆ alkyl, C ₁ -C ₆ alkylcarbonyloxy C ₁ -C ₆ alkyl, cyclo C ₃ -C ₇ alkylcarbonyloxy C ₁ -C ₆ alkyl, C ₁ -C ₆ alkoxycarbonyloxy C ₁ -C ₆ alkyl, cyclo C ₃ -C ₇ Alkyloxycarbonyloxy C ₁ -C ₆ alkyl, mono (C ₁ -C ₆ alkyl) aminocarbonyloxy C ₁ -C ₆ alkyl, di (C ₁ -C ₆ alkyl) aminocarbonyloxy C ₁ -C ₆ alkyl, ( Phenyl) aminocarbonyloxy C ₁ -C ₆ alkyl (the phenyl moiety may be substituted with J), (phenyl) (C ₁ -C ₆ alkyl) aminocarbonyloxy C ₁ -C ₆ alkyl (the phenyl moiety is J in optionally substituted), phenyl C ₁ -C ₆ alkyl (the phenyl moiety may be substituted by J) Phenyl carbonyloxy C ₁ -C ₆ alkyl (the phenyl moiety may be substituted with J), a heterocyclic group - carbonyloxy C ₁ -C ₆ alkyl (the heterocyclic moiety may be substituted with J), Phenoxycarbonyloxy C ₁ -C ₆ alkyl (the phenyl moiety may be substituted with J), C ₁ -C ₁₂ alkylcarbonyl, halo C ₁ -C ₁₂ alkylcarbonyl, C ₂ -C ₆ alkenylcarbonyl, cycloC ₃ -C ₇ alkylcarbonyl, cyclo C ₃ -C ₇ alkyl C ₁ -C ₆ alkylcarbonyl, C ₁ -C ₁₂ alkoxycarbonyl, halo C ₁ -C ₁₂ alkoxycarbonyl, (cyclo C ₃ -C ₇ alkyloxy) carbonyl , (C ₁ -C ₆ alkyl substituted cyclo C ₃ -C ₇ alkyloxy) carbonyl, C ₃ -C ₆ alkenyloxycarbonyl, halo C ₃ -C ₆ alkenyloxycarbonyl, C ₃ -C ₆ alkynyloxycarbonyl , C ₁ -C ₆ Ruki thiocarbonyl, halo C ₁ -C ₆ alkylthiocarbonyl, C ₁ -C ₆ alkoxy C ₁ -C ₆ alkylcarbonyl, C ₁ -C ₆ alkoxycarbonyl C ₁ -C ₆ alkylcarbonyl, C ₁ -C ₆ alkoxy C ₁ -C ₆ alkoxycarbonyl, C ₁ -C ₆ alkoxy C ₁ -C ₆ alkylthiocarbonyl, C ₁ -C ₆ alkylthio C ₁ -C ₆ alkoxycarbonyl, C ₁ -C ₆ alkylsulfinyl C ₁ -C ₆ alkoxycarbonyl, C ₁ -C ₆ alkylsulfonyl C ₁ -C ₆ alkoxycarbonyl, mono (C ₁ -C ₆ alkyl) aminocarbonyl, mono (halo C ₁ -C ₆ alkyl) aminocarbonyl, di (C ₁ -C ₆ alkyl) aminocarbonyl , Di (halo C ₁ -C ₆ alkyl) aminocarbonyl, phenylcarbonyl (the phenyl moiety may be substituted with J), phenyl C ₂ -C ₆ alkenylcarbonyl (the phenyl moiety may be substituted with J ) Phenyl C ₁ -C ₆ alkoxycarbonyl (the phenyl moiety may be substituted with J), phenylhalo C ₁ -C ₆ alkoxycarbonyl (the phenyl moiety may be substituted with J), phenoxycarbonyl (the phenyl moiety is Optionally substituted with J), phenoxy C ₁ -C ₆ alkoxycarbonyl (the phenyl moiety may be substituted with J), heterocyclic group-carbonyl (the heterocyclic moiety may be substituted with J) ), C ₁ -C ₆ alkoxyoxalyl, C ₁ -C ₆ alkylsulfonyl, halo C ₁ -C ₆ alkylsulfonyl, cycloC ₃ -C ₇ alkylsulfonyl, phenylsulfonyl (the phenyl moiety may be substituted with J) Or a heterocyclic group-sulfonyl (the heterocyclic moiety may be substituted with J);
R ³ is halogen, C ₁ -C ₆ alkyl or halo C ₁ -C ₆ alkyl;
R ⁴ and R ⁵ are each a hydrogen atom, C ₁ -C ₆ alkyl or halo C ₁ -C ₆ alkyl;
T is halogen, C ₁ -C ₆ alkyl, halo C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl, cyclo C ₃ -C ₇ alkyl, cyclo C ₃ -substituted with halogen C ₇ alkyl, -OH, C ₁ -C ₆ alkoxy, halo C ₁ -C ₆ alkoxy, C ₁ -C ₆ alkoxy C ₁ -C ₆ alkoxy, C ₁ -C ₆ alkylcarbonyloxy, C ₁ -C ₆ alkylthio Halo C ₁ -C ₆ alkylthio, C ₁ -C ₆ alkyl sulfinyl, halo C ₁ -C ₆ alkyl sulfinyl, C ₁ -C ₆ alkyl sulfonyl, halo C ₁ -C ₆ alkyl sulfonyl, phenyl (the phenyl moiety is J Optionally substituted) or phenyl C ₁ -C ₆ alkyl (the phenyl moiety may be substituted with J);
W is O or S;
X is -OY, -SZ ¹ , -SO-Z ² or -SO ₂ -Z ² ;
Y is C ₁ -C ₆ alkyl substituted with A, C ₁ -C ₆ alkylcarbonyl substituted with A, C ₁ -C ₆ alkoxycarbonyl, halo C ₁ -C ₆ alkoxycarbonyl, C ₁ -C ₆ alkylthio Carbonyl, halo C ₁ -C ₆ alkylthiocarbonyl, C ₃ -C ₆ alkenyl, halo C ₃ -C ₆ alkenyl, C ₃ -C ₆ alkynyl, halo C ₃ -C ₆ alkynyl, cyclo C ₃ -C ₇ alkyl, C ₁ -C ₆ alkyl substituted cyclo C ₃ -C ₇ alkyl, halo C ₁ -C ₆ alkyl substituted cyclo C ₃ -C ₇ alkyl, phenyl (the phenyl moiety may be substituted by J) Or a heterocyclic group (the heterocyclic moiety may be substituted with J);
Z ¹ is H, hydroxy C ₁ -C ₆ alkyl, C ₁ -C ₆ alkoxy C ₁ -C ₆ alkyl, halo C ₁ -C ₆ alkoxy C ₁ -C ₆ alkyl, cyclo C ₃ -C ₇ alkyl, C ₁ -C ₆ alkyl substituted cyclo C ₃ -C ₇ alkyl, halo C ₁ -C ₆ cycloalkyl C ₃ -C substituted by alkyl ₇ alkyl or phenyl (the phenyl moiety may be substituted by J) Yes;
Z ² is hydroxy C ₁ -C ₆ alkyl, C ₁ -C ₆ alkoxy C ₁ -C ₆ alkyl, halo C ₁ -C ₆ alkoxy C ₁ -C ₆ alkyl, cyclo C ₃ -C ₇ alkyl, C ₁ -C ₆ alkyl substituted cyclo C ₃ -C ₇ alkyl, halo C ₁ -C ₆ cycloalkyl C ₃ -C substituted by alkyl ₇ alkyl or phenyl (the phenyl moiety may be substituted by J);
A is —OH, C ₁ -C ₆ alkoxy, halo C ₁ -C ₆ alkoxy, C ₁ -C ₆ alkoxy C ₁ -C ₆ alkoxy, halo C ₁ -C ₆ alkoxy C ₁ -C ₆ alkoxy, C _1- C ₆ alkylthio, halo C ₁ -C ₆ alkylthio, C ₁ -C ₆ alkylsulfinyl, halo C ₁ -C ₆ alkylsulfinyl, C ₁ -C ₆ alkylsulfonyl, halo C ₁ -C ₆ alkylsulfonyl, mono (C ₁ -C ₆ alkyl) amino, di (C ₁ -C ₆ alkyl) amino, cyclo C ₃ -C ₇ alkyl, C ₁ -C ₆ alkyl substituted cyclo C ₃ -C ₇ alkyl, halo C ₁ -C ₆ alkyl substituted cyclo C ₃ -C ₇ alkyl, phenyl (the phenyl moiety may be substituted with J), phenyl C ₁ -C ₆ alkoxy (the phenyl moiety may be substituted with J), phenoxy (The phenyl moiety may be substituted with J), a heterocyclic group (the heterocyclic moiety may be substituted with J), cyano or nitro Ri;
J is halogen, C ₁ -C ₆ alkyl, halo C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl, halo C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl, halo C ₂ -C ₆ alkynyl, cyclo C ₃ -C ₇ alkyl, halogen substituted cyclo C ₃ -C ₇ alkyl, -OH, C ₁ -C ₆ alkoxy, halo C ₁ -C ₆ alkoxy, C ₁ -C ₆ alkylthio, halo C ₁ -C ₆ alkylthio, C ₁ -C ₆ alkyl sulfinyl, halo C ₁ -C ₆ alkyl sulfinyl, C ₁ -C ₆ alkyl sulfonyl, halo C ₁ -C ₆ alkyl sulfonyl, C ₁ -C ₆ alkyl carbonyl, halo C ₁ -C ₆ alkylcarbonyl, carboxyl, C ₁ -C ₆ alkoxycarbonyl, halo C ₁ -C ₆ alkoxycarbonyl, amino, mono (C ₁ -C ₆ alkyl) amino, mono (halo C ₁ -C ₆ alkyl) amino, di ( C ₁ -C ₆ alkyl) amino, di (halo C ₁ -C ₆ alkyl) amino, cyano or nitro;
m is an integer from 0 to 2;
n is an integer of 0 to 5], or a salt thereof.

  The present invention also provides a herbicide containing the heteroarylsulfonamide compound of the general formula (I) or a salt thereof as an active ingredient, an herbicidally effective amount of the compound or a salt thereof, an undesired plant, or a plant in which it grows. The present invention relates to a method of applying to a place to control undesirable plants or to suppress their growth.

  The heteroaryl sulfonamide compound of the general formula (I) or a salt thereof realizes a significant improvement in herbicidal activity against undesirable plants (weeds) as compared to similar conventional compounds. In addition, it has high safety for crops.

  Examples of the halogen atom in the general formula (I) or the halogen as a substituent include fluorine, chlorine, bromine or iodine atoms. The number of halogen atoms as substituents may be 1 or 2 or more, and in the case of 2 or more, each halogen atom may be the same or different. Further, the halogen atom may be substituted at any position.

Examples of the alkyl or alkyl moiety in the general formula (I) include, for example, methyl, ethyl, normal propyl, isopropyl, normal butyl, isobutyl, secondary butyl, tertiary butyl, normal pentyl, neopentyl, normal hexyl, normal heptyl, normal octyl. , Normal or branched C ₁ -C ₁₂ groups such as normal nonyl, normal decyl, normal undecyl, and normal dodecyl. Further, it may be a C ₁ -C ₆ group depending on the position of the substituent.

Examples of the alkoxy or alkoxy moiety in the general formula (I) include methoxy, ethoxy, propoxy, isopropoxy, butoxy, pentyloxy, hexyloxy, heptyloxy, octyloxy, nonyloxy, decyloxy, undecyloxy, and dodecyloxy. Such linear or branched C ₁ -C ₁₂ groups can be mentioned. Further, it may be a C ₁ -C ₆ group depending on the position of the substituent.

Examples of the alkenyl or alkenyl moiety in the general formula (I) include vinyl, 1-propenyl, 2-propenyl, isopropenyl, 2-methyl-1-propenyl, 1-methyl-1-propenyl, and 2-methyl-2. -Propenyl, 1-methyl-2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-hexenyl , A linear or branched C ₂ -C ₆ group such as 2,3-dimethyl-2-butenyl. Depending on the position of the substituent, the alkenyl or alkenyl moiety may be a linear or branched C ₃ -C ₆ group.

Examples of the alkynyl or alkynyl moiety in the general formula (I) include ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 2-methyl- Examples thereof include linear or branched C ₂ -C ₆ groups such as 3-butynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl and 5-hexynyl. Depending on the position of the substituent, the alkynyl or alkynyl moiety may be a linear or branched C ₃ -C ₆ group.

Examples of the cycloalkyl or cycloalkyl moiety in the general formula (I) include C ₃ -C ₇ groups such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and cycloheptyl.

The cycloalkyloxy moiety in the general formula (I) represents a (cycloalkyl) -O— group, and includes, for example, C ₃ − such as cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cycloheptyloxy. And a C ₇ group.

General formula (I) in the "C ₁ -C ₆ alkylcarbonyloxy C ₁ -C ₆ alkyl" includes C ₁ -C ₆ alkyl group and a carbonyl group of the bound "(C ₁ -C ₆ alkyl ) —C (═O) —O— (C ₁ -C ₆ alkyl) -group ”. Other similar substituents in general formula (I) are listed in Table A.

In the general formula (I), “may be substituted with J” means that when J is substituted, J may be 1 or more. “Substituted with A” means that A may be 1 or more, and similarly, “substituted with C ₁ -C ₆ alkyl” or “halo C ₁ -C ₆ alkyl” “Substituted” means that C ₁ -C ₆ alkyl or halo C ₁ -C ₆ alkyl may be one or more. When the number of substitutions of the aforementioned substituents J, A, C ₁ -C ₆ alkyl or halo C ₁ -C ₆ alkyl is 2 or more, each substituent may be the same or different. In addition, the substitution position of each substituent may be any position.

  The heterocyclic group in the general formula (I) is a 3 to 6 membered heterocyclic group containing 1 to 4 O, S or N, or a 5 to 6 member containing 1 to 2 O, S or N. A condensed heterocyclic group of a heterocyclic ring and a benzene ring is represented. Specific examples include oxolanyl, oxetanyl, tetrahydrofuranyl, tetrahydropyranyl, 1,3-dioxolan-2-yl, 1,3-dioxolan-4-yl, 1,4-dioxane-2-yl, 1,3- Dioxane-2-yl, 1,3-dioxane-4-yl, tetrahydrothiophen-2-yl, tetrahydrothiopyran-2-yl, 1,3-dithian-2-yl, 1,4-dithian-2-yl 1,4-thioxan-2-yl, 1,4-thioxan-3-yl, thienyl, furyl, pyrrolyl, oxazolyl, isoxazolyl, isoxazolinyl, thiazolyl, isothiazolyl, pyrazolyl, imidazolyl, 1,3,4- Oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,4-triazolyl, 1,2,3-triazolyl, 1,2,3-thiadiazolyl, 1,2,3,4-tetrazolyl, pyridyl, pyrimidyl, pyrazinyl, pyri Dinyl, 1,3,5-triazinyl, 1,2,4-triazinyl, benzothienyl, benzofuryl, indolyl, benzothiazolyl, benzimidazolyl, benzisoxazolyl, benzoisothiazolyl, indazolyl, benzoxazolyl, quinolyl, isoquinolyl Quinoxalinyl, phthalazinyl, cinnolinyl, quinazolinyl, imidazolinyl, imidazolidinyl, pyrazolinyl, pyrazolidinyl and the like.

  The salt of the heteroarylsulfonamide compound of the general formula (I) includes any salt that is agriculturally acceptable. For example, alkali metal salts such as sodium salt and potassium salt; magnesium Salts, alkaline earth metal salts such as calcium salts; amine salts such as dimethylamine salts and triethylamine salts; inorganic acid salts such as hydrochlorides, perchlorates, sulfates and nitrates; acetates, methanesulfonic acid Examples thereof include organic acid salts such as salts.

  In the heteroarylsulfonamide compound of the general formula (I), there may be isomers such as diastereoisomers and optical isomers. In the present invention, both isomers and isomer mixtures are present. included. In this specification, isomers are described as a mixture unless otherwise specified. The present invention includes various isomers other than the isomers within the scope of common technical knowledge in the technical field. In addition, depending on the type of isomer, the chemical structure may be different from that of the general formula (I). However, those skilled in the art may have a relationship between the chemical structure and the general formula (I). Obviously, it is well recognized and within the scope of the present invention.

The heteroarylsulfonamide of the general formula (I) or a salt thereof (hereinafter abbreviated as the compound of the present invention) can be produced according to the following production method, a usual salt production method, and a synthesis example described later. The method for obtaining the inventive compound is not limited to these methods.
・ Production method [1]

(In the formula, Q, R ¹ , R ³ , R ⁴ , R ⁵ , T, W, X, m and n are as described above, R ^2-a is C ₁ -C ₆ alkyl, halo C _1- C ₆ alkyl, C ₃ -C ₆ alkenyl, C ₃ -C ₆ alkynyl, C ₁ -C ₆ alkoxy C ₁ -C ₆ alkyl, C ₁ -C ₆ alkylcarbonyloxy C ₁ -C ₆ alkyl, cyclo C _3- C ₇ alkylcarbonyloxy C ₁ -C ₆ alkyl, C ₁ -C ₆ alkoxycarbonyloxy C ₁ -C ₆ alkyl, cyclo C ₃ -C ₇ alkyloxycarbonyloxy C ₁ -C ₆ alkyl, mono (C ₁ -C ₆ alkyl) aminocarbonyloxy C ₁ -C ₆ alkyl, di (C ₁ -C ₆ alkyl) aminocarbonyloxy C ₁ -C ₆ alkyl, (phenyl) aminocarbonyloxy C ₁ -C ₆ alkyl (the phenyl moiety is J (Optionally substituted), (phenyl) (C ₁ -C ₆ alkyl) aminocarbonyloxy C ₁ -C ₆ alkyl (the phenyl moiety may be substituted with J), phenyl C ₁ -C ₆ alkyl (the phenyl moiety may be substituted with J), phenylcarbonyloxy C ₁ -C ₆ alkyl (the phenyl moiety may be substituted with J), heterocyclic group-carbonyloxy C ₁ -C ₆ alkyl (heterocyclic moiety may be substituted with J), phenoxycarbonyloxy C ₁ -C ₆ alkyl (phenyl moiety may be substituted with J), C ₁ -C ₁₂ alkyl carbonyl, halo C ₁ -C ₁₂ alkylcarbonyl, C ₂ -C ₆ alkenylcarbonyl, cyclo C ₃ -C ₇ alkylcarbonyl, cyclo C ₃ -C ₇ alkyl C ₁ -C ₆ alkylcarbonyl, C ₁ -C ₁₂ alkoxycarbonyl Halo C ₁ -C ₁₂ alkoxycarbonyl, (cycloC ₃ -C ₇ alkyloxy) carbonyl, (C ₁ -C ₆ alkyl substituted cyclo C ₃ -C ₇ alkyloxy) carbonyl, C ₃ -C ₆ alkenyl Oxycarbonyl, halo C ₃ -C ₆ alkenyloxy Aryloxycarbonyl, C ₃ -C ₆ alkynyloxy-carbonyl, C ₁ -C ₆ alkylthiocarbonyl, halo C ₁ -C ₆ alkylthiocarbonyl, C ₁ -C ₆ alkoxy C ₁ -C ₆ alkylcarbonyl, C ₁ -C ₆ alkoxycarbonyl C ₁ -C ₆ alkylcarbonyl, C ₁ -C ₆ alkoxy C ₁ -C ₆ alkoxycarbonyl, C ₁ -C ₆ alkoxy C ₁ -C ₆ alkylthiocarbonyl, C ₁ -C ₆ alkylthio C ₁ -C ₆ alkoxycarbonyl, C ₁ -C ₆ alkylsulfinyl C ₁ -C ₆ alkoxycarbonyl, C ₁ -C ₆ alkylsulfonyl C ₁ -C ₆ alkoxycarbonyl, mono (C ₁ -C ₆ alkyl) aminocarbonyl, mono (halo C ₁ -C ₆ Alkyl) aminocarbonyl, di (C ₁ -C ₆ alkyl) aminocarbonyl, di (haloC ₁ -C ₆ alkyl) aminocarbonyl, phenylcarbonyl (the phenyl moiety may be substituted with J), phenyl C _2- C ₆ Arkeni Rucarbonyl (the phenyl moiety may be substituted with J), phenyl C ₁ -C ₆ alkoxycarbonyl (the phenyl moiety may be substituted with J), phenylhalo C ₁ -C ₆ alkoxycarbonyl (the phenyl moiety is J may be substituted), phenoxycarbonyl (the phenyl moiety may be substituted with J), phenoxy C ₁ -C ₆ alkoxycarbonyl (the phenyl moiety may be substituted with J), heterocyclic Group-carbonyl (heterocyclic moiety may be substituted with J), C ₁ -C ₆ alkoxyoxalyl, C ₁ -C ₆ alkylsulfonyl, halo C ₁ -C ₆ alkylsulfonyl, cyclo C ₃ -C ₇ alkyl A sulfonyl, phenylsulfonyl (the phenyl moiety may be substituted with J) or a heterocyclic group-sulfonyl (the heterocyclic moiety may be substituted with J), L ¹ is a halogen atom, C ₁ -C ₆ alkyl sulfates Niruokishi, represents a leaving group such as phenyl sulfonyloxy optionally substituted by C ₁ -C ₆ alkyl. )
The compound represented by the general formula (Ib) can be produced by reacting the compound represented by the general formula (Ia) with the compound represented by the general formula L ¹ -R ^2-a .

  The above reaction can be performed in the presence of a solvent, if necessary. The solvent is not particularly limited as long as it is inert to the reaction. For example, halogenated hydrocarbons such as methylene chloride, chloroform, dichloroethane, trichloroethane, carbon tetrachloride; benzene, toluene, xylene, nitrobenzene, chlorobenzene and the like. Aromatic hydrocarbons; esters such as methyl acetate, ethyl acetate, propyl acetate; acetonitrile, N, N-dimethylformamide (DMF), dimethyl sulfoxide (DMSO), dimethylacetamide (DMA), hexamethylphosphate triamide (HMPA), aprotic polar solvents such as sulfolane; ethers such as diethyl ether, tertiary butyl methyl ether, 1,4-dioxane, tetrahydrofuran (THF), 1,2-dimethoxyethane; methanol, ethanol, Al, like isopropanol Lumpur acids; water; and the like. As a solvent, these 1 type (s) or 2 or more types can be selected suitably.

  The above reaction can be carried out in the presence of a base as necessary. The base may be either an organic base or an inorganic base. Examples of the organic base include tertiary amines such as triethylamine and diisopropylethylamine; 1,8-diazabicyclo [5.4.0] -7-undecene (DBU); pyridine; 4- (dimethylamino) pyridine; 6-lutidine; and the like. Examples of the inorganic base include alkali metal carbonates such as sodium carbonate, potassium carbonate and cesium carbonate; alkali metal hydrogen carbonates such as sodium hydrogen carbonate and potassium hydrogen carbonate; alkaline earth metals such as calcium carbonate and barium carbonate Metal carbonates; alkali metal hydroxides such as lithium hydroxide, sodium hydroxide and potassium hydroxide; alkaline earth metal hydroxides such as calcium hydroxide and barium hydroxide; sodium methoxide, sodium ethoxide, Alkali metal alkoxides such as potassium tertiary butoxide; alkali metal hydrides such as sodium hydride and potassium hydride; alkali metal alkyls such as butyl lithium; alkali metal carboxylates such as sodium acetate and potassium acetate; It is done. As the base, one or more of these may be appropriately selected and mixed for use.

  The above reaction can be carried out in the presence of a phase transfer catalyst, if necessary. Examples of the phase transfer catalyst include quaternary ammonium salts such as tetranormal butyl ammonium bromide and benzyl triethyl ammonium bromide; 18-crown 6-ether; The above reaction can be carried out in the presence of additives such as trimethylamine hydrochloride and potassium iodide.

The reaction temperature for the above reaction is usually in the range from 0 ° C. to the boiling point of the solvent used, and the reaction time is usually in the range of 1 minute to 48 hours.
・ Production method [2]

(In the formula, Q, R ¹ , R ³ , R ⁴ , R ⁵ , T, X, m and n are as described above.)
The compound represented by the general formula (Ic) can be produced by reacting the compound represented by the general formula (II), which can be produced by the method described later, with the compound represented by the general formula (III). The compound of the general formula (III) is, for example, Tetrahedron, 69, 2319-2326 (2013), J. Org. Chem., 67, 7869-7871 (2002), Bulletin of the Chemical Society of Japan, 65, 3064-3067. (1992), Tetrahedron Asymmetry, 14, 2587-2594 (2003), Tetrahedron, 58, 3137-3143 (2002), J. Org. Chem., 57, 5741-5747 (1992).
The above reaction can be carried out according to the method (reaction conditions) described in JP2011-37746 and the aforementioned Patent Document 3.
・ Production method [3]

(In the formula, Q, R ¹ , R ³ , R ⁴ , R ⁵ , T, X, m and n are as described above, R ^2-b is a paramethoxybenzyl (PMB) group, 2,4-dimethoxy Protecting group such as benzyl group.)
The compound represented by the general formula (Ic) can be produced by deprotecting the compound represented by the general formula (Id).

  The above reaction can be performed using trifluoroacetic acid, and triethylsilane or the like may be added. .

When performing using trifluoroacetic acid, it can be performed in the presence of a solvent, if necessary. The solvent is not particularly limited as long as it is inert to the reaction. For example, halogenated hydrocarbons such as methylene chloride, chloroform, dichloroethane, trichloroethane, and carbon tetrachloride; aromatics such as benzene, toluene, xylene, and chlorobenzene. Hydrocarbons; esters such as methyl acetate, ethyl acetate, propyl acetate; acetonitrile, N, N-dimethylformamide (DMF), dimethyl sulfoxide (DMSO), N, N-dimethylacetamide (DMA), hexamethylphosphorus Aprotic polar solvents such as acid triamide (HMPA), sulfolane; ethers such as diethyl ether, tertiary butyl methyl ether, 1,4-dioxane, tetrahydrofuran (THF), 1,2-dimethoxyethane; Can be mentioned. As a solvent, these 1 type (s) or 2 or more types can be selected suitably. The reaction temperature is usually within the range from 0 ° C. to the boiling point of the solvent used, and the reaction time is within the range of 1 minute to 200 hours.
・ Production method [4]

(In the formula, Q, R ¹ , R ³ , R ⁴ , R ⁵ , T, X, m and n are as described above.)
The compound represented by the general formula (Ie) can be produced by reacting the compound represented by the general formula (Ic) with a sulfurizing agent.
Examples of the sulfiding agent used in the above reaction include phosphorus pentasulfide and Lawesson's reagent.

  The above reaction can be carried out in the presence of a solvent. The solvent is not particularly limited as long as it is inert to the reaction. For example, halogenated hydrocarbons such as methylene chloride, chloroform, dichloroethane, trichloroethane, and carbon tetrachloride; aromatics such as benzene, toluene, xylene, and chlorobenzene. Hydrocarbons such as normal hexane and normal heptane; ethers such as diethyl ether, tertiary butyl methyl ether, 1,4-dioxane, tetrahydrofuran (THF), 1,2-dimethoxyethane; etc. Is mentioned. As a solvent, these 1 type (s) or 2 or more types can be selected suitably.

The reaction temperature for the above reaction is usually within the range from 20 ° C. to the boiling point of the solvent used, and the reaction time is usually within the range of 1 minute to 72 hours.
・ Production method [5]

(In the formula, Q, R ¹ , R ^2-b , R ³ , R ⁴ , R ⁵ , T, m and n are as described above, L ² is a halogen atom, and L ³ is C ₁ -C ₆ alkylsulfonyloxy, phenylsulfonyloxy optionally substituted with C ₁ -C ₆ alkyl, X ¹ is —O—R ⁶ or —S—R ⁷ , and R ⁶ is C ₁ substituted with A ₁ -C ₆ alkyl, C ₁ -C ₆ alkyl carbonyl substituted with A, C ₃ -C ₆ alkenyl, halo C ₃ -C ₆ alkenyl, C ₃ -C ₆ alkynyl, halo C ₃ -C ₆ alkynyl, cyclo C ₃ -C ₇ alkyl, C ₁ -C ₆ alkyl substituted cyclo C ₃ -C ₇ alkyl, halo C ₁ -C ₆ alkyl substituted cyclo C ₃ -C ₇ alkyl, phenyl (the phenyl moiety by J Optionally substituted) or a heterocyclic group (the heterocyclic moiety may be substituted with J), R ⁷ is C ₁ -C ₆ alkyl, halo C ₁ -C ₆ alkyl, hydroxy C _1- C ₆ alkyl, C ₁ -C ₆ alkoxy C ₁ -C ₆ alkyl, halo C ₁ -C ₆ alkoxy C ₁ -C ₆ alkyl, cyclo C ₃ -C ₇ alkyl, C ₁ -C ₆ alkyl substituted cyclo C ₃ -C ₇ alkyl, halo C ₁ Cyclo C ₃ -C ₇ alkyl or phenyl substituted with —C ₆ alkyl (the phenyl moiety may be substituted with J), M is silver, etc.)
Each process of manufacturing method [5] is explained in full detail below.
・ Production method [5-1]
General formula (IV-a) → General formula (If)
The compound represented by the general formula (If) can be produced by reacting a compound represented by the general formula (IV-a) with thiol or a metal salt thereof, or alcohol or a metal salt thereof.

The said reaction can be achieved by making the thiolate adjusted with the corresponding thiol and the inorganic base and the alkoxide adjusted with the corresponding alcohol and the inorganic base act.
As an inorganic base used by the said reaction, the thing similar to the said manufacturing method [1] etc. are mentioned, for example, These 1 type (s) or 2 or more types can be selected suitably.
The solvent used in the above reaction is not particularly limited as long as it is inert to the reaction, and examples thereof include those similar to the above production method [1]. One or more of these may be appropriately selected. Can do.
The above reaction can be performed in the presence of an additive such as a phase transfer catalyst or potassium iodide, if necessary. Examples of the phase transfer catalyst include those similar to the production method [1].

The reaction temperature for the above reaction is usually in the range from 0 ° C. to the boiling point of the solvent used, and the reaction time is usually in the range of 1 minute to 48 hours.
・ Production method [5-2]
General formula (IV-a) → General formula (IV-b)
The above reaction can be performed according to the method described in Tetrahedron Asymmetry, 14, 2587-2594 (2003) and the like.
・ Production method [5-3]
General formula (IV-b) → General formula (IV-c)
The above reaction is a reaction to convert the hydroxyl C ₁ -C ₆ alkylsulfonyloxy, and to a leaving group such as C ₁ -C ₆ phenyl sulfonyloxy optionally substituted by alkyl, for example methanesulfonylation or paratoluene Sulfonylation should be performed according to the method described in Tetrahedron Lett., 44, 7981-7984 (2003), Bull. Chem. Soc. Jpn., 65, 3064-3067 (1992), WO2011 / 146335, US4772597, etc. Can do.
・ Production method [5-4]
General formula (IV-a) → General formula (IV-c)
The above reaction is a reaction in which a halogen atom such as bromine is converted to C ₁ -C ₆ alkylsulfonyloxy and the like. For example, J. Org. Chem., 78, 1718-1729 (2013), European Journal of Organic Chemistry , 1435-1439 (2010), and the like.
For example, in the case of using silver methanesulfonate (CAS No. 2386-52-9), the solvent used is not particularly limited as long as it is inert to the reaction. For example, the same as in the above production method [1] Etc., and one or more of these can be selected as appropriate.

The reaction temperature of the above reaction is usually in the range from 0 ° C. to the boiling point of the solvent used, preferably in the range of 20 ° C. to 80 ° C., and the reaction time is usually in the range of 0.1 to 48 hours. It can be carried out.
・ Production method [5-5]
General formula (IV-c) → General formula (If)
The above reaction can be carried out according to the production method [5-1].
・ Production method [6]

(In the formula, Q, R ¹ , R ³ , R ⁴ , R ⁵ , T, m and n are as described above, and R ^2-c is a hydrogen atom or a paramethoxybenzyl (PMB) group, 2 , 4-dimethoxybenzyl group and the like, X ² is —O—R ⁸ or —S—R ⁷ (R ⁷ is as described above), and R ⁸ is C ₁ -C substituted with A Substituted with ₆ alkyl, C ₃ -C ₆ alkenyl, halo C ₃ -C ₆ alkenyl, C ₃ -C ₆ alkynyl, halo C ₃ -C ₆ alkynyl, cyclo C ₃ -C ₇ alkyl, C ₁ -C ₆ alkyl cycloalkyl C ₃ -C ₇ alkyl, halo C ₁ -C ₆ cycloalkyl C ₃ -C substituted by alkyl ₇ alkyl or phenyl (the phenyl moiety may be substituted with J).)
The above reaction is carried out by reacting an alcohol (HO-R ⁸ ) and thiol (HS-R ⁷ ) corresponding to the X ² site with an α, β-unsaturated carbonyl compound (IV-d) together with a base.

  In the above reaction, a solvent may be used as necessary. For example, halogenated hydrocarbons such as methylene chloride, chloroform, dichloroethane, trichloroethane, carbon tetrachloride; benzene, toluene, xylene, nitrobenzene, chlorobenzene, etc. Aromatic hydrocarbons; aprotic polar solvents such as acetonitrile, N, N-dimethylformamide (DMF), dimethyl sulfoxide (DMSO), dimethylacetamide (DMA), hexamethylphosphoric triamide (HMPA), sulfolane; diethyl And ethers such as ether, tertiary butyl methyl ether, 1,4-dioxane, tetrahydrofuran (THF) and 1,2-dimethoxyethane; alcohols such as tertiary butanol and isopropanol; water; As a solvent, these 1 type (s) or 2 or more types can be selected suitably.

  The base used in the above reaction may be either an organic base or an inorganic base. Examples of the organic base include 1,8-diazabicyclo [5.4.0] -7-undecene (DBU); phosphazene base. Examples of the inorganic base include alkali metal carbonates such as sodium carbonate, potassium carbonate, and cesium carbonate; alkaline earth metal carbonates such as calcium carbonate and barium carbonate; sodium methoxide, sodium ethoxide, potassium tertiary butoxide And alkali metal alkoxides such as sodium hydride and potassium hydride. As the base, one or more of these may be appropriately selected and mixed for use.

The reaction temperature for the above reaction is usually in the range from 0 ° C. to the boiling point of the solvent used, and the reaction time is usually in the range of 1 minute to 48 hours.
・ Production method [7]

(In the formula, Q, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , T, Y, m, and n are as described above.)
The above reaction may be carried out under conditions used for protecting hydroxyl groups (for example, tetrahydropyranyl (THP) group, methoxymethyl (MOM) group and acetyl (Ac) group), such as GREEN'S PROTECTIVE GROUPS in Organic Synthesis; 4th Edition (John Wiley and Sons, 2007, Peter GM Wuts, Theodora W. Greene).
・ Production method [8]

(In the formula, Q, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , T, Z ² , m and n are as described above.)
The above reaction is an oxidation reaction of sulfur. For example, in halogenated hydrocarbons such as methylene chloride, chloroform and dichloroethane, a compound represented by the general formula (Ii) and an oxidizing agent such as metachloroperbenzoic acid are used. This is done by reacting. The above reaction can be carried out according to the method described in, for example, J. Org. Chem., 57, 5743-5747 (1992), Org. Lett., 11, 4386-4389 (2009).

Next, a method for producing an intermediate compound (hereinafter simply referred to as an intermediate) used in the present invention is shown below.
Intermediate production method [A]

(In the formula, Q, R ¹ , R ³ , L ² and m are as described above, and R ⁹ is C ₁ -C ₁₂ alkyl.)
Each step of the intermediate production method [A] will be described in detail below.

Intermediate production method [A-1]
General formula (V) → General formula (Va) or General formula (Vb)
The above reaction is a sulfonylation reaction of intermediate (V) that is commercially available or that can be synthesized according to a known method, and can be performed in the presence of a solvent, if necessary. The solvent is not particularly limited as long as it is inert to the reaction. For example, halogenated hydrocarbons such as methylene chloride, chloroform, dichloroethane, trichloroethane, carbon tetrachloride; benzene, toluene, xylene, nitrobenzene, chlorobenzene and the like. Aromatic hydrocarbons; esters such as methyl acetate, ethyl acetate, propyl acetate; acetonitrile, N, N-dimethylformamide (DMF), dimethyl sulfoxide (DMSO), dimethylacetamide (DMA), hexamethylphosphate triamide (HMPA), aprotic polar solvents such as sulfolane; ethers such as diethyl ether, tertiary butyl methyl ether, 1,4-dioxane, tetrahydrofuran (THF), 1,2-dimethoxyethane; . As a solvent, these 1 type (s) or 2 or more types can be selected suitably.

  The above reaction can be carried out in the presence of a base as necessary. The base may be either an organic base or an inorganic base. Examples of the organic base include tertiary amines such as triethylamine and diisopropylethylamine; 1,8-diazabicyclo [5.4.0] -7-undecene (DBU); pyridine; 4- (dimethylamino) pyridine; 6-lutidine; and the like. Examples of the inorganic base include alkali metal carbonates such as sodium carbonate, potassium carbonate and cesium carbonate; alkali metal hydrogen carbonates such as sodium hydrogen carbonate and potassium hydrogen carbonate; alkaline earth metals such as calcium carbonate and barium carbonate Metal carbonates; alkali metal hydrides such as sodium hydride and potassium hydride; alkali metal alkyls such as butyl lithium; and the like. As the base, one or more of these may be appropriately selected and mixed for use.

The reaction temperature of the above reaction is usually within a range of −70 ° C. to 150 ° C., desirably within a range of −20 ° C. to 50 ° C., and a reaction time is usually within a range of 1 minute to 72 hours. it can.
The above reaction can be carried out in the presence of an inert gas as required. Examples of the inert gas include argon gas and nitrogen gas.
Intermediate production method [A-2]
General formula (Vb) → General formula (Va)
The above reaction can be performed in the presence of a solvent, if necessary. The solvent is not particularly limited as long as it is inert to the reaction, and examples thereof include those similar to the production method [1]. One or more of these can be appropriately selected.

The above reaction can be carried out in the presence of a base as necessary. The base may be either an organic base or an inorganic base. Examples of the organic base include ammonia and hydroxylamine. Examples of the inorganic base include those similar to the above production method [1], and one or more of these can be appropriately selected and mixed for use.
The above reaction can be carried out in the presence of a phase transfer catalyst, if necessary. Examples of the phase transfer catalyst include those similar to the production method [1].

  The reaction temperature for the above reaction is usually within the range from 0 ° C. to the boiling point of the solvent used, and the reaction time is usually within the range of 1 minute to 72 hours.

Intermediate production method [A-3]
General formula (Va) or general formula (Vb) → General formula (Vc)
The above reaction is a deprotection reaction from an ester to a carboxylic acid, and can be performed according to a known method. For example, a base can be used, and examples of the inorganic base include alkali metal carbonates such as sodium carbonate, potassium carbonate, and cesium carbonate; alkali metal bicarbonates such as sodium bicarbonate and potassium bicarbonate; calcium carbonate Alkaline earth metal carbonates such as barium carbonate; alkali metal hydroxides such as lithium hydroxide, sodium hydroxide and potassium hydroxide; alkaline earth metal hydroxides such as calcium hydroxide and barium hydroxide Alkali metal alkoxides such as sodium methoxide, sodium ethoxide, potassium tertiary butoxide, and the like. Moreover, these 1 type (s) or 2 or more types can be selected and mixed suitably, and can be used.

  The solvent used in the above reaction is not particularly limited as long as it is inert to the reaction. For example, acetonitrile, N, N-dimethylformamide (DMF), dimethyl sulfoxide (DMSO), dimethylacetamide (DMA), hexamethylphosphoric acid Aprotic polar solvents such as triamide (HMPA) and sulfolane; ethers such as diethyl ether, tertiary butyl methyl ether, 1,4-dioxane, tetrahydrofuran (THF) and 1,2-dimethoxyethane; methanol, ethanol And alcohols such as isopropanol; water and the like. As a solvent, these 1 type (s) or 2 or more types can be selected suitably.

The reaction temperature for the above reaction is usually within a range of 0 ° C to 100 ° C, and the reaction time is usually within a range of 1 minute to 72 hours.
Intermediate production method [A-4]
General formula (Va), general formula (Vb) or general formula (Vc) → general formula (II)
Examples of the reducing agent used in the above reaction include lithium aluminum hydride, diisobutylaluminum hydride, sodium bis (2-methoxyethoxy) aluminum hydride, sodium borohydride, lithium borohydride, and borane THF complex. It is done.

The solvent used in the above reaction is not particularly limited as long as it is inert to the reaction. For example, halogenated hydrocarbons such as methylene chloride, chloroform, dichloroethane, trichloroethane, carbon tetrachloride; benzene, toluene, xylene, Aromatic hydrocarbons such as chlorobenzene; ethers such as diethyl ether, tertiary butyl methyl ether, 1,4-dioxane, tetrahydrofuran (THF), 1,2-dimethoxyethane; and the like. As a solvent, these 1 type (s) or 2 or more types can be selected suitably.
The reaction temperature for the above reaction is usually within the range from -70 ° C. to the boiling point of the solvent used, and the reaction time is usually within the range of 1 minute to 72 hours.

The above reaction can be carried out in the presence of an inert gas as required. Examples of the inert gas include argon gas and nitrogen gas.
Intermediate production method [B]

(In the formula, Q, R ¹ , R ^2-b , R ³ , R ⁴ , R ⁵ , R ⁹ , T, L ¹ , L ² , m and n are as described above.)
Each step of the intermediate production method [B] will be described in detail below.
Intermediate production method [B-1]
General formula (V) → General formula (VI)
The above reaction can be achieved by reductive amination of the amine compound represented by the general formula (V) and an aldehyde (for example, 4-methoxybenzaldehyde or 2,4-dimethoxybenzaldehyde) corresponding to the R ^2-b site. This reaction can be performed according to the method described in, for example, J. Org. Chem., 61, 3849-3862 (1996).
Intermediate production method [B-2]
General formula (VI) → General formula (VII)
The above reaction can be carried out according to the intermediate production method [A-1].
Intermediate production method [B-3]
General formula (VII) → General formula (VIII)
The above reaction can be carried out according to the intermediate production method [A-4].
Intermediate production method [B-4]
General formula (VIII) → General formula (IX)
The above reaction is a reaction for converting a hydroxyl group into a leaving group such as a halogen atom, C ₁ -C ₆ alkylsulfonyloxy, phenylsulfonyloxy optionally substituted with C ₁ -C ₆ alkyl.

Halogenation reaction, for example, N- chlorosuccinimide (NCS) - triphenylphosphine (PPh _3), carbon tetrachloride -PPh _3, carbon tetrabromide -PPh _3, iodine - be carried out by a combination of such imidazole -PPh ₃ Can do. The sulfonylation reaction can be carried out with sulfonyl chlorides such as methanesulfonyl chloride and p-toluenesulfonyl chloride, and the organic base exemplified in the production method [1].

  The solvent used in the above reaction is not particularly limited as long as it is inert to the reaction, and examples thereof include those similar to the intermediate production method [A-1]. One or more of these may be used. Can be appropriately selected.

The reaction temperature for the above reaction is usually within the range from 0 ° C. to the boiling point of the solvent used, and the reaction time is usually within the range of 1 minute to 72 hours.
Intermediate production method [B-5]
General formula (IX) → General formula (X)
The above reaction can be produced by a reaction between the intermediate (IX) and an intermediate (III-a) which is commercially available or can be synthesized according to a known method.

  The above reaction can be performed in the presence of a solvent, if necessary. The solvent is not particularly limited as long as it is inert to the reaction. For example, halogenated hydrocarbons such as methylene chloride, chloroform, dichloroethane, trichloroethane, carbon tetrachloride; benzene, toluene, xylene, nitrobenzene, chlorobenzene and the like. Aromatic hydrocarbons; esters such as methyl acetate, ethyl acetate, propyl acetate; acetonitrile, N, N-dimethylformamide (DMF), dimethyl sulfoxide (DMSO), dimethylacetamide (DMA), hexamethylphosphate triamide (HMPA), aprotic polar solvents such as sulfolane; ethers such as diethyl ether, tertiary butyl methyl ether, 1,4-dioxane, tetrahydrofuran (THF), 1,2-dimethoxyethane; . As a solvent, these 1 type (s) or 2 or more types can be selected suitably.

The base used in the above reaction may be either an organic base or an inorganic base, and examples thereof include those similar to the above production method [1]. One or more of these may be appropriately selected and mixed for use. be able to.
The above reaction can be carried out in the presence of a phase transfer catalyst, if necessary. Examples of the phase transfer catalyst include those similar to the production method [1]. The above reaction can be performed in the presence of an additive such as potassium iodide.

The reaction temperature for the above reaction is usually in the range from 0 ° C. to the boiling point of the solvent used, and the reaction time is usually in the range of 10 minutes to 48 hours.
Intermediate production method [B-6]
General formula (X) → General formula (IV-a-1)
In the above reaction, for example, a tertiary amine such as triethylamine is reacted with trimethylsilyl trifluoromethanesulfonate in a halogenated hydrocarbon such as methylene chloride, chloroform or dichloroethane, and then trimethylphenylammonium tribromide is reacted. This can be achieved by the action of such a brominating agent.
The reaction temperature for the above reaction is usually within a range of −20 ° C. to room temperature, and the reaction time is usually within a range of 1 minute to 48 hours.

  In addition, the manufacturing method of the intermediate body used when manufacturing this invention compound is not limited to the manufacturing method of the said illustration, You may employ | adopt any manufacturing method. Each starting material is not limited to the compounds exemplified above, and any compound may be used as long as it can produce the compound of the present invention.

The compounds of the present invention can control a wide range of undesirable plants such as annual and perennial weeds. Specifically, for example, barnyardgrass or barnyardgrass (barnyardgrass (Echinochloa crus-galli L. , Echinochloa oryzicola vasing.)), Crabgrass (crabgrass (Digitaria sanguinalis L., Digitaria ischaemum Muhl., Digitaria adscendens Henr., Digitaria microbachne Henr., Digitaria horizontalis Willd.)), Green foxtail ( Setaria viridis L.)), Akino foxtail ( Setaria faberi Herrm.)), Yellow foxtail ( Setaria lutescens Hubb.), Goosegrass ( Eleusine indica ) .)), Oats (wild oat ( Avena fatua L.)), sorghum sorghum (johnsongrass ( Sorghum halepense L.)), shibamugi (quackgrass ( Agropyron repens L.)), velvet millet (alexandergrass ( Brachiaria plantaginea )), guinea millet guineagrass ( Panicum maximum Jacq.)), paragrass ( Panicum purpurascens ), yellow squirrel (smooth witchgrass ( Panicum dichotomiflorum ), azegaya (sprangletop ( Lep tochloa chinensis)), Itoazegaya (red sprangletop (Leptochloa panicea)) , annual bluegrass (annual bluegrass (Poa annua L.) ), foxtail (black grass (Alopecurus myosuroides Huds. )), Kamojigusa (cholorado bluestem (Agropyron tsukushiense (Honda ) Ohwi )), Meriken Nik millet (broadleaf signalgrass (Brachiaria platyphylla Nash) ), Shinkurinoiga (southern sandbur (Cenchrus echinatus L.) ), darnel (italian ryegrass (Lolium multiflorum Lam. )), bermudagrass (bermudagrass (Cynodon dactylon Pers.) ) weed grasses (gramineae) such as; Cyperus Iria (rice flatsedge (Cyperus iria L.) ), purple nutsedge (purple nutsedge (Cyperus rotundus L.) ), yellow nutsedge (yellow nutsedge (Cyperus esculentus L.) ), bulrush (Japanese bulrush ( Scirpus juncoides )), Japanese squirrel (flatsedge ( Cyperus serotinus )), Japanese cypress (small-flower umbrellaplant ( Cyperus difformis )), Japanese pine (slender spikerush ( Eleocharis) acicularis)), water chestnut (water chestnut (Eleocharis kuroguwai)) Cyperaceae weeds (cyperaceae) such as; arrowhead (Japanese ribbon waparo (Sagittaria pygmaea) ), Alismataceae (arrow-head (Sagittaria trifolia) ), alisma canaliculatum (narrowleaf waterplantain ( Alisma canaliculatum)) Alismataceae weeds (alismataceae) such as; vaginalis (monochoria (monochoria vaginalis)), monochoria korsakowii (pontederiaceae weeds such as monochoria species (monochoria korsakowii)) ( pontederiaceae); false pimpernel (false pimpernel (Lindernia pyxidaria) Aceae weeds, such as abunome ( Dopatrium junceum ), weeping weeds (plantaginaceae); knotweed (toothcup ( Rotala india )), red stem ( Ammannia multiflora ) (lythraceae); Elatine triandra Schk (. long stem waterwort (Elatine triandra SCHK)) elatinaceae weeds (elatinaceae) such as; velvetleaf (velvetleaf (Abuti lon theophrasti MEDIC.)), mallow weed (malvaceae) such as American deer (prickly sida ( Sida spinosa L.)); common cocklebur ( Xanthium strumarium L.), common ragweed ( Ambrosia elatior L) .)), Ezo fox thistle (thistle ( Breea setosa (BIEB.) KITAM.)), Hagyameme (hairy galinsoga ( Galinsoga ciliata Blake)), chamomile (wild chamomile ( Matricaria chamomilla L.)), henbit ( Lamium amplexicaule L.)), common dandelion ( Taraxacum officinale weber), horseweed ( Erigeron Canadensis L.)), compositae; black nightshade ( Solanum nigrum L.)), white nightshade Solanaceae such as morning glory (jimsonweed ( Datura stramonium )); slender amaranth ( Amaranthus viridis L.), red root pigweed ( Amaranthus retroflexus L.), white squirrel (common lambsquar ters ( Chenopodium album L.)), amaranthaceae such as mexican burningbush ( Kochia scoparia Schrad.); pale smartweed ( Polygonum lapathifolium L.), harte (ladysthumb ( Polygonum persicaria L.) )), Buckwheat (wild buckwheat ( Polygonum convolvulus L.)), Polygonum aviculare L.) Polygonaceeae; flexuous bittercress ( Cardamine flexuosa WITH.) -purse ( Capsella bursapastoris Medik.)), cruciferae such as Indian mustard ( Brassica juncea Czern.); tall morningglory ( Ipomoea purpurea L.), convolvulus (field bindweed) (convolvulus arvensis L.)), the United States morning glory (. ivyleaf morningglory (Ipomoea hederacea Jacq ) Convolvulaceae weeds such as) (convolvulaceae); purslane (common purslane (portulaca oleracea L.) of) Una Portulacaceae weeds (Portulacaceae); sicklepod (sicklepod (Cassia obtusifolia L.)) Leguminosae weeds (Fabaceae), such as; chickweed Caryophyllaceae weeds such as (common chickweed (Stellariamedia L.)) (caryophyllaceae); cleavers ( Rubiaceae ( rubiaceae ) such as catchweed ( Galium spurium L.); Euphorbiaceae (euphorbiaceae) such as threeseeded copperleaf ( Acalypha australis L.); common dayflower ( Commelina communis L.) It is possible to control various harmful weeds such as Commelinaceae. Therefore, useful crops such as corn (corn ( Zea mays L.)), soybean (soybean ( Glycine max Merr.)), Cotton (cotton ( Gossypium spp.)), Wheat (wheat ( Triticum spp.)), Rice ( rice ( Oryza sativa L.)), barley (barley ( Hordeum Vulgare L.)), rye (rye ( Secalecereale L.)), oat (oat ( Avena sativa L.)), sorghum (sorgo ( Sorghum bicolor Moench)) Rape , Brassica napus L.), sunflower (sunflower ( Helianthus annuus L.)), sugar beet (suger beet ( Beta Vulgaris L.)), sugar cane (suger cane ( Saccharum officinarum L.)), turf lawngrass ( Zoysia japonica stend )), peanuts (peanut ( Arachis hypogae a L.)), flax (flax ( Linum usitatissimum L.)), tobacco (tobacco ( Nicotiana tabacum L.)), coffee (coffee ( Coffea spp.) ) Etc., it is used effectively when controlling harmful weeds selectively or when controlling non-selective harmful weeds.

  The compound of the present invention is usually mixed with various agricultural adjuvants, powders, granules, granule wettable powders, wettable powders, tablets, pills, capsules (including forms packaged with water-soluble films), It can be prepared and applied in various forms such as aqueous suspension, oil suspension, microemulsion formulation, suspoemulsion formulation, aqueous solvent, emulsion, solution, paste, etc. As long as it fits, it can be in any conventional form used in the art.

  Adjuvants used in the formulation include solid carriers such as diatomaceous earth, slaked lime, calcium carbonate, talc, white carbon, kaolin, bentonite, kaolinite and sericite, clay, sodium carbonate, sodium bicarbonate, sodium sulfate, zeolite, starch; Water, toluene, xylene, solvent naphtha, dioxane, acetone, isophorone, methyl isobutyl ketone, chlorobenzene, cyclohexane, dimethyl sulfoxide, dimethylformamide, dimethylacetamide, N-methyl-2-pyrrolidone, alcohol and other solvents; fatty acid salts, benzoic acid Salt, alkylsulfosuccinate, dialkylsulfosuccinate, polycarboxylate, alkylsulfate, alkylsulfate, alkylarylsulfate, alkyldiglycolethersulfate, alcohol sulfate Steal salt, alkyl sulfonate, alkyl aryl sulfonate, aryl sulfonate, lignin sulfonate, alkyl diphenyl ether disulfonate, polystyrene sulfonate, alkyl phosphate ester salt, alkyl aryl phosphate, styryl aryl phosphorus Acid salt, polyoxyethylene alkyl ether sulfate, polyoxyethylene alkyl aryl ether sulfate, polyoxyethylene alkyl aryl ether sulfate, polyoxyethylene alkyl ether phosphate, polyoxyethylene alkyl aryl phosphate, Anionic fields such as polyoxyethylene aryl ether phosphate salt, naphthalene sulfonate formalin condensate, alkyl naphthalene sulfonate formalin condensate Surfactant and spreading agent; sorbitan fatty acid ester, glycerin fatty acid ester, fatty acid polyglyceride, fatty acid alcohol polyglycol ether, acetylene glycol, acetylene alcohol, oxyalkylene block polymer, polyoxyethylene alkyl ether, polyoxyethylene alkyl aryl ether, Polyoxyethylene styryl aryl ether, polyoxyethylene glycol alkyl ether, polyethylene glycol, polyoxyethylene fatty acid ester, polyoxyethylene sorbitan fatty acid ester, polyoxyethylene glycerin fatty acid ester, polyoxyethylene hydrogenated castor oil, polyoxypropylene fatty acid ester Such nonionic surfactants and spreading agents; olive oil, kapok oil, castor oil Palm oil, camellia oil, coconut oil, sesame oil, corn oil, rice bran oil, peanut oil, cottonseed oil, soybean oil, rapeseed oil, linseed oil, tung oil, such as vegetable oil or mineral oil such as liquid paraffin and the like. These adjuvants can be used by appropriately selecting one or two or more kinds without departing from the object of the present invention, and examples thereof include a bulking agent, a thickener, an anti-settling agent, an antifreezing agent, and a dispersion. Various commonly used adjuvants such as stabilizers, safeners, antifungal agents, foaming agents, disintegrating agents, binders and the like can also be used. The compounding ratio of the compound of the present invention and various adjuvants is usually 0.1: 99.9 to 95: 5, preferably 0.2: 99.8 to 85:15. In addition, the compounding method of this invention compound and various adjuvants is not specifically tested, It can mix | blend suitably according to a well-known method.

  The application amount (herbicidally effective amount) of the herbicide containing the compound of the present invention cannot be defined unconditionally due to differences in weather conditions, soil conditions, formulation forms, types of undesirable plants to be treated, application time, etc. It is applied so that the compound of the present invention per hectare is 0.1 to 5,000 g, preferably 0.5 to 3,000 g, more preferably 1 to 1,000 g. The present invention also includes a method for controlling undesirable plants by applying such herbicides.

  In addition, the herbicide containing the compound of the present invention can be mixed or used in combination with other agricultural chemicals, fertilizers, safeners and the like, and in this case, more excellent effects and functions may be exhibited. Other pesticides include herbicides, fungicides, antibiotics, plant hormones, insecticides and the like. In particular, the mixed herbicidal composition in which the compound of the present invention and one or more compounds as active ingredients of other herbicides are used in combination or in combination, the range of the applicable herb species, the timing of drug treatment, herbicidal activity Etc. can be improved in a preferred direction. In addition, the compound which is an active ingredient of the compound of the present invention and other herbicides may be used by mixing separately formulated at the time of spraying, or may be used by preparing both together. The mixed herbicidal composition is also included in the present invention.

  The mixing ratio of the compound of the present invention and the compound which is an active ingredient of other herbicides cannot be defined unconditionally due to differences in weather conditions, soil conditions, drug formulation, application time, application method, etc. Other herbicides are compounded in an amount of 0.001 to 10,000 parts by weight, preferably 0.01 to 1,000 parts by weight, of the compound which is an active ingredient with respect to parts by weight. Further, the appropriate amount to be applied is 0.1 to 10,000 g, preferably 0.2 to 5,000 g, more preferably 10 to 3,000 g as the total amount of active ingredients per hectare. The present invention also includes a method for controlling undesirable plants by application of such a mixed herbicidal composition.

  Examples of the compound that is an active ingredient of other herbicides include the following compounds (generic names; some of which are included in the application for ISO). When alkyl ester etc. exist, they are also included naturally.

  (1) 2,4-D, 2,4-D-butotyl, 2,4-D-butyl, 2,4-D dimethylammonium (2 , 4-D-dimethylammonimum), 2,4-D-diolamine (2,4-D-diolamine), 2,4-D-ethyl, 2,4-D-2-ethylhexyl (2,4-D-2-ethylhexyl), 2,4-D-isobutyl, 2,4-D-isooctyl, 2,4-D-isopropyl (2,4-D-isopropyl), 2,4-D-isopropylammonium, 2,4-D sodium (2,4-D-sodium), 2,4-D isopropanolammonium (2,4-D-isopropanolammonium), 2,4-D-trolamine (2,4-D-trolamine), 2,4-DB, 2,4-DB-butyl, 2, , 4-DB-dimethylammonium, 2,4-DB iso-o Chill (2,4-DB-isoctyl), 2,4-DB potassium (2,4-DB-potassium), 2,4-DB sodium (2,4-DB-sodium), 2,4-D choline salt (2,4-D choline salt), dichloroprop (dichlorprop), dichloroprop-butotyl, dichloroprop-dimethylammonium, dichloroprop-isoctyl, dichloroprop potassium ( dichlorprop-potassium), dichloroprop-P (dichlorprop-P), dichloroprop-P-dimethylammonium, dichloroprop-P-potassium, dichloroprop-P sodium (dichlorprop-P) P-sodium), MCPA, MCPA-butotyl, MCPA-dimethylammonium, MCPA-2-ethylhexyl MCPA-2-ethylhexyl, MCPA potassium (MCPA-potassium), MCPA sodium (MCPA-sodium), MCPA thioethyl (MCPA-thioethyl), MCPB, MCPB ethyl (MCPB-ethyl), MCPB sodium (MCPB-sodium) , Mecoprop, mecoprop-butotyl, mecoprop-sodium, mecoprop-P, mecoprop-P-butotyl, mecoprop-Pdimethyl Ammonium (mecoprop-P-dimethylammonium), mecoprop-P-2-ethylhexyl, mecoprop-P-potassium, naproanilide, clomeprop, HIA- Phenoxy compounds such as 1, 2,3,6-TBA, dicamba, dicamba-butotyl , Dicamba-diglycolamine, dicamba-dimethylammonium, dicamba-diolamine, dicamba-isopropylammonium, dicamba-potassium, Dicamba-sodium, picloram, picloram-dimethylammonium, picloram-isoctyl, picloram-potassium, picloramtri Isopropanolammonium (picloram-triisopropanolammonium), picloram-triisopropylammonium (picloram-triisopropylammonium), picloram-trolamine, triclopyr (triclopyr), triclopyr-butotyl, triclopyr-butotyl Ammonium, tripypropanol, clopyralid, clopyralid-olamine, clopyralid-potassium, clopyralid-triisopropanolammonium, aminopyralid, aminocyclopyrachlor ), Aromatic carboxylic acid compounds such as halauxifen, halauxifen-methyl, DAS-534; other, naptalam, naptalam-sodium, benazoline ( benazolin, benazolin-ethyl, quinclorac, quinmerac, diflufenzopyr, diflufenzopyr-sodium, fluroxypyr , Fluroxypyr-2-butoxy-1-methylethyl, fluroxypyr-meptyl, chloroflurenol, chlorflurenol-methyl Compounds such as clacyfos, which are said to show herbicidal efficacy by disrupting the hormonal action of plants.

  (2) chlorotoluron, diuron, fluometuron, linuron, isoproturon, metobenzuron, tebuthiuron, dimefuron, isouron, isouron Carbutilate, metabenzthiazron, metoxuron, metoburomuron, monolinuron, neburon, siduron, terbumeton, trietadine, etiazine Uremic compounds: simazine, atrazine, atratone, simetryn, prometryn, dimethametryn, hexazinone, metribuzin, -Triazine compounds such as terbuthylazine, cyanazine, ametrin, cybutryne, terbutryn, propazine, metamitron, prometon; bromacil Uracil compounds such as bromacyl-lithium, lenacil, terbacil; anilide compounds such as propanil, cypromid; swep, desmedifam (Desmedipham), carbamate compounds such as phenmedipham; bromoxynil, bromoxynil-octanoate, bromoxynil-heptanoate, ioxynil , Ioxynil Hydroxybenzonitrile compounds such as ioxynil-octanoate, ioxynil-potassium, ioxynil-sodium; others, pyridate, bentazone, bentazone sodium ( Compounds such as bentazone-sodium, amicarbazone, methazole, pentanochlor, phenmedipham, and the like that show herbicidal activity by inhibiting plant photosynthesis.

  (3) Quaternary ammonium salt compounds such as paraquat and diquat, which are said to themselves become free radicals in the plant and generate active oxygen to show rapid herbicidal efficacy.

  (4) Nitrofen, Chlomethoxyfen, bifenox, acifluorfen, acifluorfen-sodium, fomesafen, fomesafen-sodium ), Oxyfluorfen, lactofen, aclonifen, ethoxyfen-ethyl, fluoroglycofen-ethyl, fluoroglycofen, and other diphenyl ether compounds; Like chlorphthalim, flumioxazin, flumiclorac, flumiclorac-pentyl, cinidon-ethyl, fluthiacet-methyl, EK-5385 Other cyclic imide compounds; oxadiargyl, oxadiazon, sulfentrazone, carfentrazone-ethyl, thidiazimin, pentoxazone, azafenidin ), Isopropazole, pyraflufen-ethyl, benzfendizone, butafenacil, saflufenacil, fluazolate, profluazol, profluazol, full Fenpyr-ethyl, bencarbazone, tiafenacil, pyrachlonil, trifludimoxazin, HNPC-B4047, IR-6396, EK-5439, EK-5498, SYN- 523, compounds described in WO2008 / 008763 (FMC), etc. As inhibits chlorophyll biosynthesis of plants, the compounds photosensitizer peroxide material is to exhibit herbicidal activity by causing abnormal accumulation in the plant.

  (5) Pyridazinone compounds such as norflurazon, chloridazon, metflurazon; pyrazolynate, pyrazoxifene, benzofenap, topramezone, pyrazole photole (Pyrasulfotole), pyrazole compounds such as tolpyralate; others, amitrole, fluridone, flurtamone, diflufenican, methoxyphenone, clomazone, sulfoto Sulcotrione, mesotrione, tembotrione, tefuryltrione, fenquinotrione, cyclopyrimorate, isoxaflutol isoxaflutole, difenzoquat, difenzoquat-metilsulfate, isoxachlorotole, benzobicyclon, bicyclopyron, picolinafen, biflubutamide (beflubutamid) Inhibiting plant pigment biosynthesis such as carotenoids, such as compounds described in, ketospiradox, ketospiradox-potassium, JP2012 / 2571 (Sumitomo Chemical) A compound that is said to show efficacy.

  (6) Dicloofop-methyl, diclofop, pyriphenop-sodium, fluazifop-butyl, fluazifop, fluazifop-P (fluazifop-P) Fluazifop-P-butyl, haloxyfop-methyl, haloxyfop, haloxyfop-etotyl, haloxyfop-P, haloxyhop -P-methyl, quizalofop-ethyl, quizalofop-P, quizalofop-P-ethyl, quizalofop-P-ethyl (quizalofop-P-ethyl) quizalofop-P-tefuryl), cyhalofop-butyl, fenoxaprop-ethyl, phenoxaprop-P fenoxaprop-P), fenoxaprop-P-ethyl, metamifop-propyl, metamifop, clodinafop-propargyl, clodinafop, Aryloxyphenoxypropionic acid compounds such as propaquizafop, HNPC-A8169 and SYP-1924; alloxydim-sodium, alloxydim, clethodim, sethoxydim, tolalcoxidim (Tralkoxydim), butroxydim, tepraloxydim, profoxydim, cyclohexanedione compounds such as cycloxydim; phenylpyrazolin compounds such as pinoxaden; and so on Inhibits fatty acid biosynthesis , The compounds to exhibit herbicidal activity plants.

  (7) Chlorimuron-ethyl, chlorimuron, sulfometuron-methyl, sulfometuron, primisulfuron-methyl, primisulfuron, Bensulfuron-methyl, bensulfuron, chlorsulfuron, methsulfuron-methyl, metsulfuron, cinosulfuron, pyrazosulfuron-ethyl , Pyrazosulfuron, flazasulfuron, rimsulfuron, nicosulfuron, imazosulfuron, flucetosulfuron, cyclosulfamuron, prosulfururon (Prosulfuron), flupirsulfuron-methyl-sodium, flupirsulfuron, triflusulfuron-methyl, triflusulfuron, halosulfuron-methyl, Halosulfuron, thifensulfuron-methyl, thifensulfuron, ethoxysulfuron, oxasulfuron, ethametsulfuron, ethametsulfuron, ethametsulfuron -methyl), iodosulfuron, sodium iodosulfuron-methyl-sodium, sulfosulfuron, triasulfuron, tribenuron-methyl, tribenuron ( tribenuron, tritosulfuron, foramsulfuron, trifloxysulfuron, trifloxysulfuron-sodium, mesosulfuron-methyl, mesosulfuron, Orthosulfamuron, amidosulfuron, azimsulfuron, propyrisulfuron, metazosulfuron, methiopyrsulfuron, monosulfuron-methyl, monosulfuron-methyl Sulfonylurea compounds such as orthosulfuron, iofensulfuron, iofensulfuron-sodium; flumetsulam, metosulam, dichroic Triazolopyrimidine sulfonamide compounds such as diclosulam, cloransulam-methyl, florasulam, penoxsulam, pyroxsulam; imazapyr, imazapyr isopropylammonium (Imazapyr-isopropylammonium), imazetapyr (imazethapyr), imazethapyr-ammonium, imazaquin, imazaquin-ammonium, imazamox, imazamox-ammonium , Imazamethabenz, imazamethabenz-methyl, imidazolinone compounds such as imazapic; pyrithiobac-sodium, bispyribac-sodium , Pyrimidinyl salicylic acid compounds such as pyriminobac-methyl, pyribenzoxim, pyrifalid, pyrimisulfan, triafamone; flucarbazone, full carbazone sodium ( sulfonylaminocarbonyltriazolinone compounds such as flucarbazone-sodium, propoxycarbazone-sodium, propoxycarbazone, thiencarbazone-methyl; other, glyphosate, Glyphosate-sodium, glyphosate-potassium, glyphosate-ammonium, glyphosate-diammonium, glyphosate isopropyl Ammonium (glyphosate-isopropylammonium), glyphosate-trimesium, glyphosate-sesquisodium, glufosinate, glufosinate-ammonium, glufosinate-P, glufosinate-P Inhibits plant amino acid biosynthesis, such as ammonium (glufosinate-P-ammonium), glufosinate-P sodium (glufosinate-P-sodium), vilanafos (bilanafos), vilanafos sodium (bilanafos-sodium), cinmethylin A compound that is said to show herbicidal efficacy.

  (8) Trifluralin, oryzalin, oryzalin, nitalin, pendimethalin, ethalluralin, benfluralin, prodiamine, butralin, dinitramine ( dinitroaniline compounds such as dinitramine; amide compounds such as bensulide, napropamide, napropamide-M, propyzamide, and pronamide; amiprophosmethyl ( Organophosphorous compounds such as amiprofos-methyl, butamifos, anilofos, piperophos; such as propham, chlorpropham, barban, carbetamide Phenyl carbamate compounds Cumylamine compounds such as daimuron, cumyluron, bromobutide, methyldymron; others, ashram, asuram-sodium, dithiopyr, thiazopyr ), Chlorthal-dimethyl, chlorthal, diphenamid, flamprop-M-methyl, flamprop-M, flamprop-M- Compounds such as isopropyl (flamprop-M-isopropyl) that are said to show herbicidal efficacy by inhibiting plant cell mitosis.

  (9) Alachlor, metazachlor, butachlor, pretilachlor, metolachlor, S-metolachlor, tenylchlor, petoxamide Chloroacetamide compounds such as acetochlor, acetochlor, propachlor, dimethenamide, dimethenamide-P, propisochlor, dimethachlor; molinate Dimepiperate, pyributicarb, EPTC, butyrate, vernolate, pebulate, cycloate, prosulfocarb, esprocarb, chi Thiocarbamate compounds such as thiobencarb, dialate, diallate, tri-allate, orbencarb; etobenzanid, mefenacet, flufenacet, tri Didiphane, caffenstrole, fentrazamide, oxaziclomefone, indanofan, benfuresate, pyroxasulfone, fenoxasulfone, methiozoline Inhibiting plant protein or lipid biosynthesis, such as methiozolin, dalapon, dalapon-sodium, TCA sodium (TCA-sodium), trichloroacetic acid The compound which is supposed to show herbicidal efficacy in.

  (10) Compounds that exhibit herbicidal activity by inhibiting cellulose biosynthesis in plants such as dichlobenil, triaziflam, indaziflam, flupoxam, isoxaben, etc. .

  (11) MSMA, DSMA, CMA, endothal (endothall), endothal-dipotassium, endothal sodium (endothall-sodium), endtal mono (N, N-dimethylalkylammonium) (endothall-mono ( N, N-dimethylalkylammonium)), etofumesate, sodium chlorate, pelargonic acid, nonanoic acid, phosamine, fosamine-ammonium, ipfen Carbazone (ipfencarbazone), aclolein, ammonium sulfamate, borax, chloroacetic acid, sodium chloroacete, cyanamide, methylarsonic acid ), Dimethylarsonic acid (Dimethylarsinic acid), sodium dimethylarsinate, dinoterb, dinoterb-ammonium, dinoterb-diolamine, dinoterb-acetate, DNOC, sulfuric acid Ferrous sulfate, flupropanate, sodium flupropanate (flupropanate-sodium), mefluidide, mefluidide-diolamine, metam, metam ammonium ( metam-ammonium, metam-potassium, metam-sodium, methyl isothiocyanate, pentachlorophenol, sodium pentachlorophenoxide, pentachlorophenol laurate (Pentachlorophenol laurate), quinoclamine, sulfuric acid, urea sulfate, xanthinosin, herbimycin, anguinol, metatyrosine, sarmentine, taxitomine A (thaxtominA), mevalocidin, alpha-limonene, pyribambenz-propyl, pyribambenz-isopropyl, JS-913, KHG-23844, H-9201 , SIOC-0163, SIOC-0171, SIOC-0172, SIOC-0285, SIOC-0426, SIOC-H-057, ZJ-0166, ZJ-1835, ZJ-0453, ZJ-0777, ZJ-0862, WO2008 / 096398 Other herbicides such as compounds described in (Kumiai Chemistry).

(12) Xanthomonas campestris (Xanthomonas campestris), epi heart Sils Nematosorusu (Epicoccosirus nematosorus), epi heart Sils Nematosuperasu (Epicoccosirus nematosperus), Ekiserohiramu monoceras (Exserohilum monoseras), parasitic plants such as Drechslera monoceras (Drechsrela monoceras) It is supposed to show herbicidal efficacy by doing.

  The said compound which is an active ingredient of another herbicide can select 1 type (s) or 2 or more types suitably. The active ingredients of other herbicides are not limited to the compounds exemplified above.

  EXAMPLES Hereinafter, the present invention will be described in more detail with reference to examples. However, the present invention is not construed as being limited to the examples. First, the synthesis example of this invention compound is described.

Synthesis example 1
S-isopropyl (2-{[3- (methoxymethoxy) -2-oxopiperidin-1-yl] methyl} thiophen-3-yl) [(trifluoromethyl) sulfonyl] carbamothioate (Compound No. 1-14 )

(1) 1,1,1-trifluoro-N- {2-[(2-oxopiperidin-1-yl) methyl] thiophen-3-yl} that can be synthesized by the method described in Synthesis Example 1 of WO2013 / 061973 Methanesulfonamide (4.38 g), potassium carbonate (2.65 g) and 4-methoxybenzyl chloride (5.78 g) were added to acetonitrile (50 ml), and the mixed solution was stirred under reflux conditions for 6 hours. After cooling to room temperature, 2N aqueous hydrochloric acid was added to stop the reaction. The reaction solvent was distilled off under reduced pressure, and the residue was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The resulting crude 1,1,1-trifluoro-N- (4-methoxybenzyl) -N- { By solidifying 2-[(2-oxopiperidin-1-yl) methyl] thiophen-3-yl} methanesulfonamide in a mixed solvent of normal heptane and ethyl acetate, 1,1,1-trifluoro-N -(4-Methoxybenzyl) -N- {2-[(2-oxopiperidin-1-yl) methyl] thiophen-3-yl} methanesulfonamide (3.90 g) was obtained as a beige powder.
¹ H-NMR (500 MHz, acetone-d6, δppm): 7.45 (d, 1H), 7.16-7.19 (m, 2H), 7.12 (d, 1H), 6.88-6.91 (m, 2H), 3.78 (s , 3H), 3.50-5.30 (br, 4H), 2.57 (br, 2H), 2.22-2.24 (m, 2H), 1.66-1.71 (m, 2H), 1.56-1.61 (m, 2H).

(2) 1,1,1-trifluoro-N- (4-methoxybenzyl) -N- {2-[(2-oxopiperidin-1-yl) methyl] thiophen-3-yl} methanesulfonamide (3.90 g) and triethylamine (2.35 ml) were dissolved in chloroform (36 ml) and ice-cooled under a nitrogen atmosphere. Trimethylsilyl trifluoromethanesulfonate (2.28 ml) was added dropwise thereto, and the mixture was stirred for 1 hour while cooling with ice. Trimethylphenylammonium tribromide (3.33 g) was added little by little, then the ice bath was removed, the mixture was stirred at room temperature for 23 hours, and water was added to stop the reaction. The aqueous layer was separated and extracted with chloroform. The organic layers were combined, washed with saturated brine, dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure, and the resulting residue was purified by column chromatography (heptane: ethyl acetate = 1: 1). -{2-[(3-Bromo-2-oxopiperidin-1-yl) methyl] thiophen-3-yl} -1,1,1-trifluoro-N- (4-methoxybenzyl) methanesulfonamide (4.06 g) was obtained as a yellow oil.
¹ H-NMR (500 MHz, acetone-d6, δppm): 7.50 (d, 1H), 7.16-7.18 (m, 3H), 6.90-6.92 (m, 2H), 4.59-4.61 (m, 1H), 3.79 (s, 3H), 3.50-5.60 (br, 4H), 2.74-2.81 (m, 2H), 2.24-2.31 (m, 1H), 2.11-2.15 (m, 1H), 1.90-2.03 (brm, 1H) , 1.60-1.67 (m, 1H).

(3) N- {2-[(3-bromo-2-oxopiperidin-1-yl) methyl] thiophen-3-yl} -1,1,1-trifluoro-N- (4-methoxybenzyl) methane Sulfonamide (3.04 g) was dissolved in acetonitrile (30 ml), potassium acetate (0.90 g) and 18-crown 6-ether (0.15 g) were added thereto, and the reaction solution was heated and refluxed with 1 Stir for hours. After cooling to room temperature, 2N aqueous hydrochloric acid solution was added, and the reaction solvent was evaporated under reduced pressure. The residue was extracted with ethyl acetate, and the organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to obtain crude acetic acid 2-oxo-1-({3- [1, 1,1-trifluoro-N- (4-methoxybenzyl) methylsulfonamido] thiophen-2-yl} methyl) piperidin-3-yl (3.04 g) was obtained.

(4) Crude acetic acid 2-oxo-1-({3- [1,1,1-trifluoro-N- (4-methoxybenzyl) methylsulfonamido] thiophen-2-yl obtained in (3) above } Methyl) piperidin-3-yl (3.04 g) was dissolved in ethanol (60 ml), and 2N aqueous sodium hydroxide solution (10 ml) was added at room temperature. Further methanol (30 ml) was added and the reaction solution was stirred at room temperature for 1.5 hours. A 1N aqueous hydrochloric acid solution (30 ml) was added and the mixture was stirred for a while, and the resulting solid was collected by filtration. Furthermore, methanol and ethanol were distilled off from the filtrate under reduced pressure, and the resulting solid was collected by filtration. The solids obtained by filtration were combined and dried under reduced pressure to obtain 1,1,1-trifluoro-N- {2-[(3-hydroxy-2-oxopiperidin-1-yl) methyl] thiophene- 3-yl} -N- (4-methoxybenzyl) methanesulfonamide (2.51 g) was obtained.

(5) 1,1,1-trifluoro-N- {2-[(3-hydroxy-2-oxopiperidin-1-yl) methyl] thiophen-3-yl} -N- (4-methoxybenzyl) methane Sulfonamide (1.00 g), triethylsilane (1.0 ml) and trifluoroacetic acid (5.0 ml) were mixed, heated in an oil bath at 90 ° C., and stirred under reflux conditions for 19 hours. After cooling to room temperature, the reaction solution was concentrated under reduced pressure, and the resulting residue was purified by column chromatography (heptane: ethyl acetate = 7: 3 to 1: 1) to obtain 1,1,1-trifluoro-N. -{2-[(3-Hydroxy-2-oxopiperidin-1-yl) methyl] thiophen-3-yl} methanesulfonamide (506 mg) was obtained.
¹ H-NMR (500 MHz, acetone-d6, δppm): 11.43 (brs, NH), 7.48 (d, 1H), 7.11 (d, 1H), 4.65 (d, 1H), 4.58 (d, 1H), 4.36 (brs, OH), 4.07 (dd, 1H), 3.51-3.61 (m, 2H), 2.05-2.13 (m, 1H), 1.95-2.02 (m, 1H), 1.83-1.92 (m, 1H), 1.64-1.72 (m, 1H).

(6) 1,1,1-trifluoro-N- {2-[(3-hydroxy-2-oxopiperidin-1-yl) methyl] thiophen-3-yl} methanesulfonamide (685 mg) and pyridine ( 0.30 ml) was dissolved in THF (10 ml), and S-isopropylchlorothioformate (0.33 g) was added thereto while stirring at room temperature. After 1 hour, S-isopropylchlorothioformate (0.10 g) was further added, and the mixture was stirred at room temperature for 13 hours. 2N hydrochloric acid aqueous solution was added to stop the reaction, and the mixture was extracted with ethyl acetate. The organic layer is washed with saturated brine, dried over anhydrous sodium sulfate, the solvent is distilled off under reduced pressure, and the resulting residue is purified by column chromatography (heptane: ethyl acetate = 7: 3 to 6: 4). , S-isopropyl {2-[(3-hydroxy-2-oxopiperidin-1-yl) methyl] thiophen-3-yl} [(trifluoromethyl) sulfonyl] carbamothioate (838 mg) was obtained as a solid .
¹ H-NMR (500 MHz, acetone-d6, δppm): 7.62 (d, 1H), 7.06 (d, 1H), 4.80-4.92 (brm, 1H), 4.50-4.70 (brm, 1H), 4.00-4.08 (m, 1H and -OH), 3.54-3.62 (m, 1H), 3.40 (br, 2H), 2.13-2.18 (m, 1H), 1.82-2.00 (m, 2H), 1.64-1.72 (m, 1H ), 1.29-1.32 (m, 6H).

(7) S-isopropyl {2-[(3-hydroxy-2-oxopiperidin-1-yl) methyl] thiophen-3-yl} [(trifluoromethyl) sulfonyl] carbamothioate (324 mg) and N, N-diisopropylethylamine (0.40 ml) was dissolved in chloroform (7 ml) and ice-cooled under a nitrogen atmosphere. Chloromethyl methyl ether (0.20 ml) was added dropwise thereto, and the mixture was stirred while raising the temperature to room temperature. After 5 hours, the mixture was cooled again in an ice bath, and N, N-diisopropylethylamine (0.20 ml) and chloromethyl methyl ether (0.10 ml) were added. After stirring at room temperature for 45 hours, water was added to stop the reaction. The aqueous layer was extracted with chloroform, and the combined organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, the solvent was evaporated under reduced pressure, and the resulting residue was subjected to column chromatography (heptane: ethyl acetate = 7: 3) to obtain the desired product (315 mg, Compound No. 1-14) as a light brown oil.

Synthesis example 2
N- (2-{[3- (allyloxy) -2-oxopiperidin-1-yl] methyl} thiophen-3-yl) -1,1,1-trifluoro-N- (4-methoxybenzyl) methanesulfone Synthesis of Amide (Compound No. 1-65) 1,1,1-trifluoro-N- {2-[(3-hydroxy-2-oxopiperidine synthesized by the method described in Synthesis Example 1 (4) -1-yl) methyl] thiophen-3-yl} -N- (4-methoxybenzyl) methanesulfonamide (1.14 g) and potassium iodide (0.12 g) were added to THF (20 ml) and stirred at room temperature. Sodium hydride (0.13 g, 60 wt%) was added. After stirring for 5 minutes under a nitrogen atmosphere, allyl bromide (0.41 ml) was added, and the reaction solution was heated and stirred for 2.5 hours under reflux conditions. After cooling to room temperature with stirring, a saturated aqueous ammonium chloride solution was added to stop the reaction, and the mixture was extracted with ethyl acetate. The organic layer is washed with saturated brine, dried over anhydrous sodium sulfate, the solvent is distilled off under reduced pressure, and the resulting residue is purified by column chromatography (heptane: ethyl acetate = 9: 1 to 4: 6). The target product (855 mg, Compound No. 1-65) was obtained.

Synthesis example 3
N- (2-{[3- (allyloxy) -2-oxopiperidin-1-yl] methyl} thiophen-3-yl) -1,1,1-trifluoromethanesulfonamide (Compound No. 1-9) Composition
N- (2-{[3- (allyloxy) -2-oxopiperidin-1-yl] methyl} thiophen-3-yl) -1,1,1-trifluoro-N- (4-methoxybenzyl) methanesulfone Amide (854 mg), triethylsilane (0.80 ml) and trifluoroacetic acid (5.0 ml) were mixed, heated in an oil bath at 90 ° C., and stirred under reflux conditions for 3 hours. After cooling to room temperature, the reaction solution was concentrated under reduced pressure, and the resulting residue was purified by column chromatography (heptane: ethyl acetate = 9: 1 to 7: 3) to obtain the desired product (556 mg, Compound No. 1). -9) was obtained with a pale purple oil.

Synthesis example 4
Synthesis of isopropyl (2-{[3- (allyloxy) -2-oxopiperidin-1-yl] methyl} thiophen-3-yl) [(trifluoromethyl) sulfonyl] carbamate (Compound No. 1-10)
N- (2-{[3- (allyloxy) -2-oxopiperidin-1-yl] methyl} thiophen-3-yl) -1,1,1-trifluoromethanesulfonamide (75 mg) and pyridine (0.10 ml ) Was dissolved in THF (3.0 ml), and isopropyl chloroformate (0.12 g) was added thereto while stirring at room temperature. After stirring overnight, 2N aqueous hydrochloric acid solution was added, and the mixture was extracted with ethyl acetate. The organic layer is washed with saturated brine, dried over anhydrous sodium sulfate, the solvent is distilled off under reduced pressure, and the resulting residue is purified by column chromatography (heptane: ethyl acetate = 9: 1 to 7: 3). The desired product (88 mg, compound No. 1-10) was obtained as a pale yellow oil.

Next, typical examples of the compounds of the present invention are listed in Tables 1 to 5. These compounds can be synthesized based on the synthesis examples or the various production methods. In Tables 1 to 5, No. represents compound No., Me represents methyl group, Et represents ethyl group, i-Pr represents isopropyl group, c-Pr represents cyclopropyl group, and c-Bu represents Cyclobutyl group, c-Pe represents a cyclopentyl group, and Ph represents a phenyl group. In the table, “Ph (4-OMe)” represents a phenyl group substituted with methoxy at the 4-position, and other similar descriptions are also based thereon. Moreover, the other abbreviations in the table indicate the following.

Table 1 lists the ¹ H-NMR spectrum data of the compounds listed in Tables 1 to 5.

Next, test examples of the present invention will be described.
・ Test Example 1
A field crop soil was filled in a 1 / 170,000 hectare pot and seeds of various plants were sown. After that, the plant had a certain leaf age ((1) barnyardgrass ( Echinochloa crus-galli L.); 0.5-2.5 leaf stage, (2) crabgrass ( Digitaria sanguinalis L.); 1.5-2.5 leaf stage ,
(3) Green foxtail ( Setariaviridis L.); 1.5-2.5 leaf stage, (4) Red root pigweed ( Amaranthus retroflexus L.); 0.2-2.0 leaf stage, (5) American golden beetle (prickly sida) ( Sida spinosa L.)); cotyledon to 1.5 leaf stage, (6) velvetleaf ( Abutilon theophrasti MEDIC.); 0.5 to 2.0 leaf stage, (7) rice (rice ( Oryza sativa L.)); 1.0 to 2.5 leaf stage, (8) corn (corn ( Zea mays L.)); 2.0-3.5 leaf stage, (9) wheat (wheat ( Triticum spp.)); 2.0-3.5 leaf stage, (10) cotton (cotton ( Gossypium spp.)); Primary leaves to 1.0 leaf stage, (11) soybean ( Glycine max Merr.); Primary leaves to 0.5 leaf stage), the compound according to the present invention is put into a conventional formulation method. A wettable powder or emulsion prepared according to the above is weighed so that the amount of the active ingredient is a predetermined amount, and water equivalent to 500 liters per hectare (agricultural spreading agent (xalino: manufactured by Nippon Agricultural Chemicals Co., Ltd.) is contained by 0.1% by volume. Diluted). The prepared spray was treated with a small spray.

  On the 14th to 21st days after the chemical treatment, the growth state of various plants was observed with the naked eye, and the herbicidal effect was evaluated at a growth inhibition rate (%) of 0 (equivalent to the untreated group) to 100 (completely killed). The results shown in Table 7 were obtained.

・ Test Example 2
1 / 170,000 hectare pot filled with upland field soil, various plants ((Barnyardgrass ( Echinochloa crus-galli L.)), barnyard (crabgrass ( Digitaria sanguinalis L.)), green foxtail ( Setaria viridis L.)) , Red root pigweed ( Amaranthus retroflexus L.), American deer (prickly sida ( Sida spinosa L.)), velvetleaf ( Abutilon theophrasti MEDIC.), Rice (rice ( oryza sativa L.)), corn (corn ( Zea mays L.)), wheat (wheat ( Triticum spp.)), cotton (cotton ( Gossypium spp.)), soybean (soybean ( Glycine max Merr.))) seeded. A wettable powder or emulsion prepared according to the usual formulation method of the compound according to the present invention is weighed so as to have a predetermined active ingredient amount, diluted in water equivalent to 500 liters per hectare, and treated with a small spray. did.

  On the 14th to 21st days after the chemical treatment, the growth state of various plants was observed with the naked eye, and the herbicidal effect was evaluated at a growth inhibition rate (%) of 0 (equivalent to the untreated group) to 100 (completely killed). The results in Table 8 were obtained.

・ Test Example 3
Paddy soil was packed in a 1 / 1,000,000 hectare pot, and seeds of barnyardgrass ( Echinochloa oryzicola vasing.) And firefly (Japanese bulrush ( Scirpus juncoides )) were sown and lightly covered with soil. Thereafter, the tube was left in a greenhouse at a depth of 0.5 to 1 cm, and the tuber of Urikawa (Japanese ribbon waparo ( Sagittaria pygmaea )) was planted the next day. Thereafter, the water depth was maintained at 3 to 4 cm, and when the Tainubier and firefly reached the 0.5 leaf stage and Urikawa reached the primary leaf stage, the compound according to the present invention was prepared according to a usual formulation method or a wettable powder or emulsion. The aqueous diluted solution was uniformly dropped with a pipette so as to obtain a predetermined active ingredient amount. In addition, paddy soil is packed in a 1 / 1,000,000 hectare pot, padded, and the water depth is 3-4 cm. The next day rice ( Oryza sativa L.) (variety: Nipponbare) is transplanted 3 cm deep Transplanted. On the day after transplantation, the compound according to the present invention was treated as described above.

  Macroscopically observe the growth of Tainubie, Firefly and Urikawa on the 12th to 17th day after the chemical treatment, and the growth state of the rice on the 11th to 19th day after the chemical treatment. Evaluation was made with a growth inhibition rate (%) of 100 (complete killing), and the results in Table 9 were obtained.

Next, formulation examples of the present invention will be described.
Formulation example 1
(1) Compound of the present invention 75 parts by weight (2) Geropone T-77 (trade name; manufactured by Rhône-Poulenc) 14.5 parts by weight (3) NaCl 10 parts by weight (4) dextrin 0.5 parts by weight or more ( A granule wettable powder is obtained by putting each component of 1) to (4) into a high-speed mixing fine granulator, adding 20% water thereto, granulating and drying.

Formulation example 2
(1) Kaolin 78 parts by weight (2) Labelin FAN (trade name; manufactured by Daiichi Kogyo Seiyaku Co., Ltd.) 2 parts by weight (3) Solpol 5039 (trade name; manufactured by Toho Chemical Industry Co., Ltd.) 5 parts by weight (4 ) Carplex (trade name; manufactured by DSL Japan Co., Ltd.) 15 parts by weight or more of the mixture of the components (1) to (4) and the compound of the present invention in a weight ratio of 9: 1 to mix the wettable powder. Is obtained.

Formulation example 3
(1) High filler No. 10 (trade name; manufactured by Matsumura Sangyo Co., Ltd.) 33 parts by weight (2) Solpol 5050 (trade name; manufactured by Toho Chemical Co., Ltd.) 3 parts by weight (3) Solpol 5073 (trade name; Toho Chemical Industries, Ltd.) Product) 4 parts by weight (4) Compound of the present invention 60 parts by weight or more of each component of (1) to (4) is mixed to obtain a wettable powder.

Formulation example 4
(1) Compound of the present invention 4 parts by weight (2) bentonite 30 parts by weight (3) calcium carbonate 61.5 parts by weight (4) Toxanone GR-31A (trade name; manufactured by Sanyo Chemical Industries, Ltd.) 3 parts by weight (5 ) Calcium lignin sulfonate 1.5 parts by weight Pre-ground (1), (2) and (3) are mixed, and (4), (5) and water are added and mixed there. Grain. Then, a granule is obtained by drying and sizing.

Formulation example 5
(1) Compound of the present invention 30 parts by weight (2) Siegrite (trade name; manufactured by Siegrite Co., Ltd.) 60 parts by weight (3) New Calgen WG-1 (trade name; manufactured by Takemoto Yushi Co., Ltd.) 5 parts by weight (4) New Calgen FS-7 (trade name; manufactured by Takemoto Yushi Co., Ltd.) 5 parts by weight The above (1), (2) and (3) are mixed, passed through a pulverizer, and (4) is added. After kneading, extrusion granulation is performed. Then, a granule wettable powder is obtained by drying and sizing.

Formulation Example 6
(1) Compound of the present invention 28 parts by weight (2) Sopropol FL (trade name; manufactured by Rhone-Poulenc) 2 parts by weight (3) Solpol 355 (trade name; manufactured by Toho Chemical Co., Ltd.) 1 part by weight (4) IP solvent 1620 (trade name; manufactured by Idemitsu Petrochemical Co., Ltd.) 32 parts by weight (5) ethylene glycol 6 parts by weight (6) water 31 parts by weight or more of each component of (1) to (6) is mixed and wetted An aqueous suspension is obtained by pulverization using a pulverizer (Dyno mill).

  The present invention is not limited to the above-described embodiments, and various modifications are possible within the scope shown in the claims, and embodiments obtained by appropriately combining technical means disclosed in different embodiments. Is also included in the technical scope of the present invention. Furthermore, a new technical feature can be formed by combining the technical means disclosed in each embodiment.

  The compounds of the present invention achieve a significant improvement in herbicidal activity against undesirable plants compared to similar conventional compounds. In addition, it has high safety for crops. Therefore, the heteroaryl sulfonamide compound or a salt thereof according to the present invention exhibits an excellent herbicidal effect when used as an active ingredient of a herbicide. The range of application ranges from paddy fields, upland fields, orchards, mulberry fields and other non-agricultural lands such as forests, farm roads, grounds, and factory premises. You can choose.

Claims (3)

Formula (I):

[Where Q is the general formula (Q-1) or general formula (Q-2):

A thiophene ring represented by:
R ¹ is haloC ₁ -C ₆ alkyl;
R ² is a hydrogen atom, C ₁ -C ₆ alkyl, halo C ₁ -C ₆ alkyl, C ₃ -C ₆ alkenyl, C ₃ -C ₆ alkynyl, C ₁ -C ₆ alkoxy C ₁ -C ₆ alkyl, C ₁ -C ₆ alkylcarbonyloxy C ₁ -C ₆ alkyl, cyclo C ₃ -C ₇ alkylcarbonyloxy C ₁ -C ₆ alkyl, C ₁ -C ₆ alkoxycarbonyloxy C ₁ -C ₆ alkyl, cyclo C ₃ -C ₇ Alkyloxycarbonyloxy C ₁ -C ₆ alkyl, mono (C ₁ -C ₆ alkyl) aminocarbonyloxy C ₁ -C ₆ alkyl, di (C ₁ -C ₆ alkyl) aminocarbonyloxy C ₁ -C ₆ alkyl, ( Phenyl) aminocarbonyloxy C ₁ -C ₆ alkyl (the phenyl moiety may be substituted with J), (phenyl) (C ₁ -C ₆ alkyl) aminocarbonyloxy C ₁ -C ₆ alkyl (the phenyl moiety is J in optionally substituted), phenyl C ₁ -C ₆ alkyl (the phenyl moiety may be substituted by J) Phenyl carbonyloxy C ₁ -C ₆ alkyl (the phenyl moiety may be substituted with J), a heterocyclic group - carbonyloxy C ₁ -C ₆ alkyl (the heterocyclic moiety may be substituted with J), Phenoxycarbonyloxy C ₁ -C ₆ alkyl (the phenyl moiety may be substituted with J), C ₁ -C ₁₂ alkylcarbonyl, halo C ₁ -C ₁₂ alkylcarbonyl, C ₂ -C ₆ alkenylcarbonyl, cycloC ₃ -C ₇ alkylcarbonyl, cyclo C ₃ -C ₇ alkyl C ₁ -C ₆ alkylcarbonyl, C ₁ -C ₁₂ alkoxycarbonyl, halo C ₁ -C ₁₂ alkoxycarbonyl, (cyclo C ₃ -C ₇ alkyloxy) carbonyl , (C ₁ -C ₆ alkyl substituted cyclo C ₃ -C ₇ alkyloxy) carbonyl, C ₃ -C ₆ alkenyloxycarbonyl, halo C ₃ -C ₆ alkenyloxycarbonyl, C ₃ -C ₆ alkynyloxycarbonyl , C ₁ -C ₆ Ruki thiocarbonyl, halo C ₁ -C ₆ alkylthiocarbonyl, C ₁ -C ₆ alkoxy C ₁ -C ₆ alkylcarbonyl, C ₁ -C ₆ alkoxycarbonyl C ₁ -C ₆ alkylcarbonyl, C ₁ -C ₆ alkoxy C ₁ -C ₆ alkoxycarbonyl, C ₁ -C ₆ alkoxy C ₁ -C ₆ alkylthiocarbonyl, C ₁ -C ₆ alkylthio C ₁ -C ₆ alkoxycarbonyl, C ₁ -C ₆ alkylsulfinyl C ₁ -C ₆ alkoxycarbonyl, C ₁ -C ₆ alkylsulfonyl C ₁ -C ₆ alkoxycarbonyl, mono (C ₁ -C ₆ alkyl) aminocarbonyl, mono (halo C ₁ -C ₆ alkyl) aminocarbonyl, di (C ₁ -C ₆ alkyl) aminocarbonyl , Di (halo C ₁ -C ₆ alkyl) aminocarbonyl, phenylcarbonyl (the phenyl moiety may be substituted with J), phenyl C ₂ -C ₆ alkenylcarbonyl (the phenyl moiety may be substituted with J ) Phenyl C ₁ -C ₆ alkoxycarbonyl (the phenyl moiety may be substituted with J), phenylhalo C ₁ -C ₆ alkoxycarbonyl (the phenyl moiety may be substituted with J), phenoxycarbonyl (the phenyl moiety is Optionally substituted with J), phenoxy C ₁ -C ₆ alkoxycarbonyl (the phenyl moiety may be substituted with J), heterocyclic group-carbonyl (the heterocyclic moiety may be substituted with J) ), C ₁ -C ₆ alkoxyoxalyl, C ₁ -C ₆ alkylsulfonyl, halo C ₁ -C ₆ alkylsulfonyl, cycloC ₃ -C ₇ alkylsulfonyl, phenylsulfonyl (the phenyl moiety may be substituted with J) Or a heterocyclic group-sulfonyl (the heterocyclic moiety may be substituted with J);
R ³ is halogen, C ₁ -C ₆ alkyl or halo C ₁ -C ₆ alkyl;
R ⁴ and R ⁵ are each a hydrogen atom, C ₁ -C ₆ alkyl or halo C ₁ -C ₆ alkyl;
T is halogen, C ₁ -C ₆ alkyl, halo C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl, cyclo C ₃ -C ₇ alkyl, cyclo C ₃ -substituted with halogen C ₇ alkyl, -OH, C ₁ -C ₆ alkoxy, halo C ₁ -C ₆ alkoxy, C ₁ -C ₆ alkoxy C ₁ -C ₆ alkoxy, C ₁ -C ₆ alkylcarbonyloxy, C ₁ -C ₆ alkylthio Halo C ₁ -C ₆ alkylthio, C ₁ -C ₆ alkyl sulfinyl, halo C ₁ -C ₆ alkyl sulfinyl, C ₁ -C ₆ alkyl sulfonyl, halo C ₁ -C ₆ alkyl sulfonyl, phenyl (the phenyl moiety is J Optionally substituted) or phenyl C ₁ -C ₆ alkyl (the phenyl moiety may be substituted with J);
W is O or S;
X is -OY, -SZ ¹ , -SO-Z ² or -SO ₂ -Z ² ;
Y is C ₁ -C ₆ alkyl substituted with A, C ₁ -C ₆ alkylcarbonyl substituted with A, C ₁ -C ₆ alkoxycarbonyl, halo C ₁ -C ₆ alkoxycarbonyl, C ₁ -C ₆ alkylthio Carbonyl, halo C ₁ -C ₆ alkylthiocarbonyl, C ₃ -C ₆ alkenyl, halo C ₃ -C ₆ alkenyl, C ₃ -C ₆ alkynyl, halo C ₃ -C ₆ alkynyl, cyclo C ₃ -C ₇ alkyl, C ₁ -C ₆ alkyl substituted cyclo C ₃ -C ₇ alkyl, halo C ₁ -C ₆ alkyl substituted cyclo C ₃ -C ₇ alkyl, phenyl (the phenyl moiety may be substituted by J) Or a heterocyclic group (the heterocyclic moiety may be substituted with J);
Z ¹ is H, hydroxy C ₁ -C ₆ alkyl, C ₁ -C ₆ alkoxy C ₁ -C ₆ alkyl, halo C ₁ -C ₆ alkoxy C ₁ -C ₆ alkyl, cyclo C ₃ -C ₇ alkyl, C ₁ -C ₆ alkyl substituted cyclo C ₃ -C ₇ alkyl, halo C ₁ -C ₆ cycloalkyl C ₃ -C substituted by alkyl ₇ alkyl or phenyl (the phenyl moiety may be substituted by J) Yes;
Z ² is hydroxy C ₁ -C ₆ alkyl, C ₁ -C ₆ alkoxy C ₁ -C ₆ alkyl, halo C ₁ -C ₆ alkoxy C ₁ -C ₆ alkyl, cyclo C ₃ -C ₇ alkyl, C ₁ -C ₆ alkyl substituted cyclo C ₃ -C ₇ alkyl, halo C ₁ -C ₆ cycloalkyl C ₃ -C substituted by alkyl ₇ alkyl or phenyl (the phenyl moiety may be substituted by J);
A is —OH, C ₁ -C ₆ alkoxy, halo C ₁ -C ₆ alkoxy, C ₁ -C ₆ alkoxy C ₁ -C ₆ alkoxy, halo C ₁ -C ₆ alkoxy C ₁ -C ₆ alkoxy, C _1- C ₆ alkylthio, halo C ₁ -C ₆ alkylthio, C ₁ -C ₆ alkylsulfinyl, halo C ₁ -C ₆ alkylsulfinyl, C ₁ -C ₆ alkylsulfonyl, halo C ₁ -C ₆ alkylsulfonyl, mono (C ₁ -C ₆ alkyl) amino, di (C ₁ -C ₆ alkyl) amino, cyclo C ₃ -C ₇ alkyl, C ₁ -C ₆ alkyl substituted cyclo C ₃ -C ₇ alkyl, halo C ₁ -C ₆ alkyl substituted cyclo C ₃ -C ₇ alkyl, phenyl (the phenyl moiety may be substituted with J), phenyl C ₁ -C ₆ alkoxy (the phenyl moiety may be substituted with J), phenoxy (The phenyl moiety may be substituted with J), a heterocyclic group (the heterocyclic moiety may be substituted with J), cyano or nitro Ri;
J is halogen, C ₁ -C ₆ alkyl, halo C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl, halo C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl, halo C ₂ -C ₆ alkynyl, cyclo C ₃ -C ₇ alkyl, halogen substituted cyclo C ₃ -C ₇ alkyl, -OH, C ₁ -C ₆ alkoxy, halo C ₁ -C ₆ alkoxy, C ₁ -C ₆ alkylthio, halo C ₁ -C ₆ alkylthio, C ₁ -C ₆ alkyl sulfinyl, halo C ₁ -C ₆ alkyl sulfinyl, C ₁ -C ₆ alkyl sulfonyl, halo C ₁ -C ₆ alkyl sulfonyl, C ₁ -C ₆ alkyl carbonyl, halo C ₁ -C ₆ alkylcarbonyl, carboxyl, C ₁ -C ₆ alkoxycarbonyl, halo C ₁ -C ₆ alkoxycarbonyl, amino, mono (C ₁ -C ₆ alkyl) amino, mono (halo C ₁ -C ₆ alkyl) amino, di ( C ₁ -C ₆ alkyl) amino, di (halo C ₁ -C ₆ alkyl) amino, cyano or nitro;
m is an integer from 0 to 2;
n is an integer of 0 to 5] or a salt thereof.   A herbicide containing the heteroarylsulfonamide compound according to claim 1 or a salt thereof as an active ingredient.   A method of applying a herbicidally effective amount of the heteroarylsulfonamide compound or a salt thereof according to claim 1 to an undesirable plant or a place where it grows, and controlling or suppressing the growth of the undesirable plant.