Nitrogen-containing heterocyclic compound having sulfonyl group, agricultural / horticultural herbicide containing same, and use thereof

Abstract

The present invention addresses the problem of providing a new herbicide which has both a high level of safety for crops and an excellent herbicidal activity against weeds. The herbicide is for overcoming a food crisis accompanying the expected increase in the global human population in the near future.　The problem is solved by: a compound represented by general formula (1) or salts thereof; an agricultural / horticultural herbicide containing said compound or salts thereof as an active ingredient; and a method of using the agricultural / horticultural herbicide.

Description

Nitrogen-containing heterocyclic compound having a sulfonyl group, agricultural and horticultural herbicide containing said compound, and method of using the same

[0001] The present invention relates to a nitrogen-containing heterocyclic compound having a sulfonyl group and a salt thereof, an agricultural and horticultural herbicide containing the compound or a salt thereof as an active ingredient, and a method for using them.

[0002] Patent Documents 1 to 5 describe that certain arylazole compounds have insecticidal activity, but these documents do not describe the specific structure of the compound of the present invention, nor do they disclose or suggest compounds useful as herbicides.

[0003] International Publication No. 2015 / 144826 Brochure International Publication No. 2017 / 104741 Brochure International Publication No. 2018 / 052035 Brochure International Publication No. 2018 / 116945 Brochure International Publication No. 2021 / 085370 Brochure

[0004] A stable supply of food is essential to alleviate the food crisis that will accompany the expected increase in world population in the near future. A stable food supply requires economical and efficient methods of killing or controlling weeds that hinder crop cultivation and harvesting, and the development of new herbicides and plant growth regulators that can solve this problem is becoming increasingly important. The present invention addresses this social need by providing a novel herbicide that is highly safe for crops and has excellent herbicidal activity against weeds.

[0005] The present inventors have conducted extensive research to develop novel agricultural and horticultural herbicides, and as a result have found that the compounds represented by general formula (I) of the present invention or salts thereof are useful as agricultural and horticultural herbicides, thereby completing the present invention.

[0006] That is, the present invention provides a compound according to the present invention, which comprises: [1] a compound of general formula (I): {In the formula, R １ is (a1) (C １ -C ６ ) alkyl group; (a2) halo(C １ -C ６ ) alkyl group; or (a3) ​​N(R ２ａ ) R２ｂ Group (wherein, R ２ａ and R ２ｂ are (b1) hydrogen atoms, (b2) (C １ -C ６ ) alkyl group, (b3) (C ２ -C ６ ) alkenyl group, (b4) (C ２ -C ６ ) an alkynyl group, (b5) (C ３ -C ６ ) cycloalkyl group, (b6) halo (C １ -C ６ ) alkyl group, (b7) (C １ -C ７ ) alkylcarbonyl group, (b8) (C １ -C ６ ) alkoxycarbonyl group, (b9) halo(C １ -C ７ ) alkylcarbonyl group, or (b10) halo (C １ -C ６ ) represents an alkoxycarbonyl group, R ２ａ and R ２ｂ may be the same or different. Het represents the formula (Het-1) or the formula (Het-2). (In the formula, R ３ (c1) a halogen atom; (c2) a cyano atom; (c3) (C １ -C ６ ) alkyl group; (c4) (C ２ -C ６ ) alkenyl group; (c5) (C ２ -C ６ ) alkynyl group; (c6) (C ３ -C ６ ) cycloalkyl group; (c7) (C １ -C ６ ) alkoxy group; (c8) halo (C １ -C ６ ) alkyl group; (c9) halo (C ２ -C ６ ) alkenyl group; (c10) halo (C ２ -C ６ ) alkynyl group; (c11) halo (C３ -C ６ ) cycloalkyl group; (c12) halo (C １ -C ６ (c13) a substituted (C) alkoxy group having 1 to 3 substituents independently selected from the substituent group S; １ -C ６ (c14) a substituted (C) alkyl group having 1 to 3 substituents independently selected from the substituent group T; ３ -C ６ ) cycloalkyl group; (c15) (C １ -C ６ ) alkylsulfanyl group; (c16) (C １ -C ６ ) alkylsulfinyl group; (c17) (C １ -C ６ ) alkylsulfonyl group; (c18) (C １ -C ６(c19) a furanyl group; (c20) a substituted furanyl group having on the ring 1 to 3 substituents each independently selected from the substituent group U; (c21) an oxazolyl group; (c22) a substituted oxazolyl group having on the ring 1 to 3 substituents each independently selected from the substituent group U; (c23) a thienyl group; (c24) a substituted thienyl group having on the ring 1 to 3 substituents each independently selected from the substituent group U; (c25) a thiazolyl group; (c26) a substituted thiazolyl group having on the ring 1 to 2 substituents each independently selected from the substituent group U; (c27) a naphthyl group; (c28) a substituted naphthyl group having on the ring 1 to 7 substituents each independently selected from the substituent group U; (c29) a phenyl group; (c30) (c31) a pyridyl group; (c32) a substituted pyridyl group having 1 to 4 substituents independently selected from the substituent group U on the ring; (c33) a pyridazinyl group; (c34) a substituted pyridazinyl group having 1 to 3 substituents independently selected from the substituent group U on the ring; (c35) a pyrimidinyl group; (c36) a substituted pyrimidinyl group having 1 to 3 substituents independently selected from the substituent group U on the ring; (c37) a pyrazinyl group; (c38) a substituted pyrazinyl group having 1 to 3 substituents independently selected from the substituent group U on the ring; (c39) phenyl (C １ -C ６ ) alkyl group; or (c40) a substituted phenyl (C １ -C ６ ) alkyl group; Y is a nitrogen atom or CR ４ (In the formula, R ４ represents a hydrogen atom, a halogen atom, or (C １ -C ６ ) represents an alkyl group. ５ａ are: (d1) hydrogen atoms; (d2) (C １ -C ６ ) alkyl group; or (d3) halo (C １ -C６ ) represents an alkyl group. ５ｂ are: (e1) hydrogen atoms; (e2) halogen atoms; (e3) (C １ -C ６ ) alkyl group; or (e4) halo (C １ -C ６ ) alkyl group. The substituent group S is: (f1) a cyano group; (f2) (C ３ -C ６ ) cycloalkyl group; (f3) (C １ -C ６ ) alkoxy group; (f4) (C １ -C ６ ) alkylsulfanyl group; (f5) (C １ -C ６ ) alkylsulfinyl group; (f6) (C １ -C ６ ) alkylsulfonyl group; (f7) halo (C ３ -C ６ ) cycloalkyl group; (f8) halo (C １ -C ６ ) alkoxy group; (f9) halo (C １ -C ６ ) alkylsulfanyl group; (f10) halo (C １ -C ６ ) alkylsulfinyl group; and (f11) halo(C １ -C ６ The substituent group T is composed of: (g1) a cyano group; (g2) (C １ -C ６ ) alkyl group; (g3) (C ３ -C ６ ) cycloalkyl group; (g4) (C １ -C ６ ) alkoxy group; (g5) (C １ -C ６ ) alkylsulfanyl group; (g6) (C １ -C ６ ) alkylsulfinyl group; (g7) (C １ -C ６ ) alkylsulfonyl group; (g8) halo (C １ -C ６) alkyl group; (g9) halo (C ３ -C ６ ) cycloalkyl group; (g10) halo (C １ -C ６ ) alkoxy group; (g11) halo (C １ -C ６ ) alkylsulfanyl group; (g12) halo(C １ -C ６ ) alkylsulfinyl group; (g13) halo(C １ -C ６ (g14) a phenyl group. The substituent group U consists of (h1) a halogen atom; (h2) a cyano group; (h3) a nitro group; (h4) an amino group; (h5) a hydroxyl group; (h6) a hydroxy (C １ -C ６ ) alkyl group; (h7) (C １ -C ６ ) alkyl group; (h8) (C ２ -C ６ ) alkenyl group; (h9) (C ２ -C ６ ) alkynyl group; (h10) (C ３ -C ６ ) cycloalkyl group; (h11) halo (C １ -C ６ ) alkyl group; (h12) halo (C ２ -C ６ ) alkenyl group; (h13) halo (C ２ -C ６ ) alkynyl group; (h14) halo (C ３ -C ６ ) cycloalkyl group; (h15) (C １ -C ６ ) alkoxy group; (h16) (C １ -C ６ ) alkylsulfanyl group; (h17) (C １ -C ６ ) alkylsulfinyl group; (h18) (C １ -C ６ ) alkylsulfonyl group; (h19) halo (C １ -C ６) alkoxy group; (h20) halo (C １ -C ６ ) alkylsulfanyl group; (h21) halo (C １ -C ６ ) alkylsulfinyl group; (h22) halo (C １ -C ６ ) alkylsulfonyl group; (h23) N—((C １ -C ６ ) alkylcarbonyl) amino group; and (h24) N—((C １ -C ６) alkylsulfonyl) amino group. ● indicates the binding site. (i1) an oxazolinyl group; (i2) a substituted oxazolinyl group having 1 to 4 substituents each independently selected from substituent group V on the ring; (i3) an imidazolinyl group; (i4) a substituted imidazolinyl group having 1 to 4 substituents each independently selected from substituent group V on the ring; (i5) an imidazolidinonyl group; (i6) a substituted imidazolidinonyl group having 1 to 4 substituents each independently selected from substituent group V on the ring; (i7) a triazolinonyl group; (i8) a substituted triazolinonyl group having 1 to 2 substituents each independently selected from substituent group V on the ring; (i9) a pyrazolinonyl group; (i10) a substituted pyrazolinonyl group having 1 to 3 substituents each independently selected from substituent group V on the ring; (i11) a pyrazolyl group; (i12) (i13) a triazolyl group; (i14) a substituted triazolyl group having on the ring one to three substituents each independently selected from substituent group V; (i15) a tetrazolyl group; (i16) a substituted tetrazolyl group having on the ring one substituent selected from substituent group V; (i17) an imidazolyl group; (i18) a substituted imidazolyl group having on the ring one to three substituents each independently selected from substituent group V; (i19) a pyrrolyl group; (i20) a substituted pyrrolyl group having on the ring one to four substituents each independently selected from substituent group V; (i21) a thiazolyl group; (i22) a substituted thiazolyl group having on the ring one to two substituents each independently selected from substituent group V; (i23) an oxazolyl group; (i24) a substituted oxazolyl group having 1 to 2 substituents independently selected from the substituent group V on the ring; (i25) tetrahydrofuranyl (C １ -C ６ ) alkoxy group; (i26) substituted tetrahydrofuranyl (C １ -C ６ ) alkoxy group; (i27) dioxolanyl (C１ -C ６ (i28) a substituted dioxolanyl (C) having 1 to 4 substituents independently selected from the substituent group V on the ring; １ -C ６ ) alkoxy group; (i29) isoxazolinyl (C １ -C ６ (i30) a substituted isoxazolinyl (C) having 1 to 4 substituents independently selected from the substituent group V on the ring; １ -C ６ ) alkoxy group; (i31) pyrazolyl (C １ -C ６ (i32) a substituted pyrazolyl (C) having 1 to 3 substituents independently selected from the substituent group V on the ring; １ -C ６ ) alkoxy group; (i33) triazolyl (C １ -C ６ (i34) a substituted triazolyl (C) having 1 to 2 substituents independently selected from the substituent group V on the ring; １ -C ６ ) alkoxy group; (i35) tetrazolyl (C １ -C ６ ) alkoxy group; (i36) substituted tetrazolyl (C) having one substituent selected from the substituent group V on the ring; １ -C ６ ) alkoxy group; (i37) imidazolyl (C １ -C ６ (i38) a substituted imidazolyl (C) having 1 to 3 substituents independently selected from the substituent group V on the ring; １ -C ６ ) alkoxy group; (i39) pyrrolyl (C １ -C ６ (i40) a substituted pyrrolyl (C １ -C ６ ) alkoxy group; (i41) thiazolyl (C １ -C ６(i42) a substituted thiazolyl (C) having 1 to 2 substituents independently selected from the substituent group V on the ring; １ -C ６ ) alkoxy group; (i43) oxazolyl (C １ -C ６ ) alkoxy group; or (i44) a substituted oxazolyl (C １ -C ６ ) alkoxy group. The substituent group V is (j1) a halogen atom; (j2) a cyano group; (j3) (C １ -C ６ ) alkyl group; (j4) (C ２ -C ６ ) alkenyl group; (j5) (C ２ -C ６ ) alkynyl group; (j6) (C ３ -C ６ ) cycloalkyl group; (j7) halo (C １ -C ６ ) alkyl group; (j8) halo (C ２ -C ６ ) alkenyl group; (j9) halo (C ２ -C ６ ) alkynyl group; (j10) halo (C ３ -C ６ ) cycloalkyl group; (j11) (C １ -C ６ ) alkoxy group; (j12) (C １ -C ６ ) alkylsulfanyl group; (j13) (C １ -C ６ ) alkylsulfinyl group; (j14) (C １ -C ６ ) alkylsulfonyl group; (j15) halo(C １ -C ６ ) alkoxy group; (j16) halo (C １ -C ６ ) alkylsulfanyl group; (j17) halo(C １ -C ６ ) alkylsulfinyl group; (j18) halo(C １-C ６ ) alkylsulfonyl group; (j19) (C １ -C ６ ) alkoxy(C １ -C ６ ) alkyl group; (j20) (C １ -C ６ ) alkylsulfanyl (C １ -C ６ ) alkyl group; (j21) (C １ -C ６ ) an alkoxycarbonyl group; (j22) a phenyl group; (j23) a halogen atom, (C １ -C ６ ) alkyl and halo(C １ -C ６ (j24) a thienyl group; and (j25) a halogen atom, (C １ -C ６ ) alkyl and halo(C １ -C ６ a substituted thienyl group having 1 to 3 substituents on the ring, each independently selected from the group consisting of alkyl, methyl ...

[0007] [2] R １ But, (a1) (C １ -C ６ ) alkyl group; or (a3') N(R ２ａ ) R ２ｂ Group (wherein, R ２ａ and R ２ｂ are (b1) hydrogen atoms, (b2) (C １ -C ６ ) alkyl group, (b5) (C ３ -C ６ ) cycloalkyl group, (b6) halo (C １ -C ６ ) alkyl group, (b7) (C １ -C ７ ) alkylcarbonyl group, or (b8) (C １ -C ６ ) represents an alkoxycarbonyl group, R ２ａ and R ２ｂmay be the same or different, Het is formula (Het-1) or formula (Het-2), R ３ (c1) a halogen atom; (c3) (C １ -C ６ ) alkyl group; (c4) (C ２ -C ６ ) alkenyl group; (c6) (C ３ -C ６ ) cycloalkyl group; (c7) (C １ -C ６ ) alkoxy group; (c8) halo (C １ -C ６ ) alkyl group; (c9) halo (C ２ -C ６ ) alkenyl group; (c11) halo (C ３ -C ６ (c13) a substituted (C) cycloalkyl group having 1 to 3 substituents independently selected from the substituent group S; １ -C ６ (c14) a substituted (C) alkyl group having 1 to 3 substituents independently selected from the substituent group T; ３ -C ６ ) cycloalkyl group; (c15) (C １ -C ６ ) alkylsulfanyl group; (c16) (C １ -C ６ ) alkylsulfinyl group; (c17) (C １ -C ６ ) alkylsulfonyl group; (c18) (C １ -C ６(c19) a furanyl group; (c20) a substituted furanyl group having 1 to 3 substituents each independently selected from the substituent group U on the ring; (c23) a thienyl group; (c24) a substituted thienyl group having 1 to 3 substituents each independently selected from the substituent group U on the ring; (c25) a thiazolyl group; (c26) a substituted thiazolyl group having 1 to 2 substituents each independently selected from the substituent group U on the ring; (c27) a naphthyl group; (c28) a substituted naphthyl group having 1 to 7 substituents each independently selected from the substituent group U on the ring; (c29) a phenyl group; (c30) a substituted phenyl group having 1 to 5 substituents each independently selected from the substituent group U on the ring; (c31) a pyridyl group; (c32) a substituted pyridyl group having 1 to 4 substituents each independently selected from the substituent group U on the ring; (c39) Phenyl (C １ -C ６ ) alkyl group; or (c40) a substituted phenyl (C １ -C ６ ) alkyl group, and Y is a nitrogen atom or CR ４ (In the formula, R ４ represents a hydrogen atom; ５ａ (d1) a hydrogen atom; or (d2) (C １ -C ６ ) alkyl group, R ５ｂ (e1) a hydrogen atom; or (e3) (C １ -C ６ ) alkyl group, and the substituent group S is (f1) a cyano group; (f2) (C ３ -C ６ ) cycloalkyl group; (f3) (C １ -C ６ ) alkoxy group; (f4) (C １ -C ６ ) alkylsulfanyl group; (f5) (C １ -C ６ ) alkylsulfinyl group; and (f6) (C １ -C ６) alkylsulfonyl group, and the substituent group T is (g1) a cyano group; (g2) (C １ -C ６ ) alkyl group; (g8) halo (C １ -C ６ (g14) a phenyl group; and (g15) a phenyl group, wherein the substituent group U is selected from the group consisting of: (h1) a halogen atom; (h2) a cyano group; (h5) a hydroxyl group; (h6) a hydroxy(C １ -C ６ ) alkyl group; (h7) (C １ -C ６ ) alkyl group; (h10) (C ３ -C ６ ) cycloalkyl group; (h11) halo (C １ -C ６ ) alkyl group; (h14) halo (C ３ -C ６ ) cycloalkyl group; (h15) (C １ -C ６ ) alkoxy group; (h16) (C １ -C ６ ) alkylsulfanyl group; (h17) (C １ -C ６ ) alkylsulfinyl group; (h18) (C １ -C ６ ) alkylsulfonyl group; (h19) halo (C １ -C ６ ) alkoxy group; (h20) halo (C １ -C ６ ) alkylsulfanyl group; (h21) halo (C １ -C ６ ) alkylsulfinyl group; (h22) halo (C １ -C ６ ) alkylsulfonyl group; and (h23) N—((C １ -C ６(i1) an oxazolinyl group; (i2) a substituted oxazolinyl group having 1 to 4 substituents each independently selected from substituent group V on the ring; (i3) an imidazolinyl group; (i4) a substituted imidazolinyl group having 1 to 4 substituents each independently selected from substituent group V on the ring; (i5) an imidazolidinonyl group; (i6) a substituted imidazolidinonyl group having 1 to 4 substituents each independently selected from substituent group V on the ring; (i7) a triazolinonyl group; (i8) a substituted triazolinonyl group having 1 to 2 substituents each independently selected from substituent group V on the ring; (i9) a pyrazolinonyl group; (i10) a substituted pyrazolinonyl group having 1 to 3 substituents each independently selected from substituent group V on the ring; (i11) (i12) a substituted pyrazolyl group having 1 to 3 substituents independently selected from the substituent group V on the ring; (i13) a triazolyl group; (i14) a substituted triazolyl group having 1 to 2 substituents independently selected from the substituent group V on the ring; (i21) a thiazolyl group; (i22) a substituted thiazolyl group having 1 to 2 substituents independently selected from the substituent group V on the ring; (i23) an oxazolyl group; (i24) a substituted oxazolyl group having 1 to 2 substituents independently selected from the substituent group V on the ring; (i25) tetrahydrofuranyl (C １ -C ６ ) alkoxy group; (i26) substituted tetrahydrofuranyl (C １ -C ６ ) alkoxy group; (i27) dioxolanyl (C １ -C ６ (i28) a substituted dioxolanyl (C) having 1 to 4 substituents independently selected from the substituent group V on the ring; １ -C ６ ) alkoxy group; (i29) isoxazolinyl (C １ -C ６(i30) a substituted isoxazolinyl (C) having 1 to 4 substituents independently selected from the substituent group V on the ring; １ -C ６ ) alkoxy group; (i31) pyrazolyl (C １ -C ６ (i32) a substituted pyrazolyl (C) having 1 to 3 substituents independently selected from the substituent group V on the ring; １ -C ６ ) alkoxy group; (i33) triazolyl (C １ -C ６ (i34) a substituted triazolyl (C) having 1 to 2 substituents independently selected from the substituent group V on the ring; １ -C ６ ) alkoxy group; (i41) thiazolyl (C １ -C ６ (i42) a substituted thiazolyl (C) having 1 to 2 substituents independently selected from the substituent group V on the ring; １ -C ６ ) alkoxy group; (i43) oxazolyl (C １ -C ６ ) alkoxy group; or (i44) a substituted oxazolyl (C １ -C ６ ) alkoxy group, and the substituent group V is (j1) a halogen atom; (j2) a cyano group; (j3) (C １ -C ６ ) alkyl group; (j4) (C ２ -C ６ ) alkenyl group; (j6) (C ３ -C ６ ) cycloalkyl group; (j7) halo (C １ -C ６ ) alkyl group; (j8) halo (C ２ -C ６ ) alkenyl group; (j10) halo (C ３ -C ６ ) cycloalkyl group; (j11) (C １ -C ６) alkoxy group; (j12) (C １ -C ６ ) alkylsulfanyl group; (j13) (C １ -C ６ ) alkylsulfinyl group; (j14) (C １ -C ６ ) alkylsulfonyl group; (j15) halo(C １ -C ６ ) alkoxy group; (j16) halo (C １ -C ６ ) alkylsulfanyl group; (j20) (C １ -C ６ ) alkylsulfanyl (C １ -C ６ ) alkyl group; (j21) (C １ -C ６ ) an alkoxycarbonyl group; (j22) a phenyl group; (j23) a halogen atom, (C １ -C ６ ) alkyl and halo(C １ -C ６ (j24) a thienyl group; and (j25) a halogen atom, (C １ -C ６ ) alkyl and halo(C １ -C ６ ) a substituted thienyl group having 1 to 3 substituents independently selected from the group consisting of alkyl,

[0008] [3] R １ But, (a1) (C １ -C ６ ) alkyl group; or (a3'') N(R ２ａ ) R ２ｂ Group (wherein, R ２ａ and R ２ｂ are (b1) hydrogen atoms, (b2) (C １ -C ６ ) alkyl group, (b7) (C １ -C ７ ) alkylcarbonyl group, or (b8) (C １ -C６ ) represents an alkoxycarbonyl group, R ２ａ and R ２ｂ may be the same or different, Het is formula (Het-1) or formula (Het-2), R ３ (c1) a halogen atom; (c3) (C １ -C ６ ) alkyl group; (c4) (C ２ -C ６ ) alkenyl group; (c6) (C ３ -C ６ ) cycloalkyl group; (c8) halo (C １ -C ６ ) alkyl group (c13) a substituted (C) group having 1 to 3 substituents independently selected from the substituent group S １ -C ６ (c14) a substituted (C) alkyl group having 1 to 3 substituents independently selected from the substituent group T; ３ -C ６ ) cycloalkyl group; (c18) (C １ -C ６ ) alkoxycarbonyl group; (c19) a furanyl group; (c23) a thienyl group; (c25) a thiazolyl group; (c26) a substituted thiazolyl group having 1 to 2 substituents independently selected from the substituent group U on the ring; (c27) a naphthyl group; (c29) a phenyl group; (c30) a substituted phenyl group having 1 to 5 substituents independently selected from the substituent group U on the ring; (c31) a pyridyl group; (c32) a substituted pyridyl group having 1 to 4 substituents independently selected from the substituent group U on the ring; or (c40) a substituted phenyl (C １ -C ６ ) alkyl group, and Y is a nitrogen atom or CR ４ (In the formula, R ４ represents a hydrogen atom; ５ａ But, (d2) (C １ -C ６ ) alkyl group, R ５ｂ (e1) a hydrogen atom; or (e3) (C１ -C ６ ) alkyl group, and the substituent group S is (f3) (C １ -C ６ ) alkoxy group, the substituent group T is (g14) a phenyl group, the substituent group U is (h1) a halogen atom; (h5) a hydroxyl group; (h6) a hydroxy(C １ -C ６ ) alkyl group; (h7) (C １ -C ６ ) alkyl group; (h11) halo (C １ -C ６ ) alkyl group; and (h15) (C １ -C ６ (i10) a substituted pyrazolinonyl group having 1 to 3 substituents independently selected from substituent group V on the ring; (i11) a pyrazolyl group; (i12) a substituted pyrazolyl group having 1 to 3 substituents independently selected from substituent group V on the ring; (i13) a triazolyl group; (i14) (i22) a substituted triazolyl group having 1 to 2 substituents independently selected from the substituent group V on the ring; (i26) a substituted tetrahydrofuranyl (C) having 1 to 4 substituents independently selected from the substituent group V on the ring; １ -C ６ (i28) a substituted dioxolanyl (C) having 1 to 4 substituents independently selected from the substituent group V on the ring; １ -C ６(i30) a substituted isoxazolinyl (C) having 1 to 4 substituents independently selected from the substituent group V on the ring; １ -C ６ ) alkoxy group; (i31) pyrazolyl (C １ -C ６ (i32) a substituted pyrazolyl (C) having 1 to 3 substituents independently selected from the substituent group V on the ring; １ -C ６ (i34) a substituted triazolyl (C) having 1 to 2 substituents independently selected from the substituent group V on the ring; １ -C ６ ) alkoxy group; or (i42) substituted thiazolyl (C １ -C ６ ) an alkoxy group, and the substituent group V is (j1) a halogen atom; (j3) (C １ -C ６ ) alkyl group; (j4) (C ２ -C ６ ) alkenyl group; (j6) (C ３ -C ６ ) cycloalkyl group; (j7) halo (C １ -C ６ ) alkyl group; (j11) (C １ -C ６ ) alkoxy group; (j12) (C １ -C ６ ) alkylsulfanyl group; (j20) (C １ -C ６ ) alkylsulfanyl (C １ -C ６ ) alkyl group; (j21) (C １ -C ６ (j23') an alkoxycarbonyl group; (j23') a substituted phenyl group having 1 to 5 substituents independently selected from halogen atoms on the ring; and (j24) a thienyl group,

[0009] [4] An agricultural and horticultural herbicide comprising the compound or salt thereof according to any one of [1] to [3] above as an active ingredient; [5] A method for using the agricultural and horticultural herbicide according to [4] above, comprising applying an effective amount of the agricultural and horticultural herbicide to weeds, soil, paddy fields, or a cultivation carrier; and [6] A method for controlling weeds, comprising applying an effective amount of the agricultural and horticultural herbicide according to [4] above to weeds, soil, paddy fields, or a cultivation carrier.

[0010] The compounds of the present invention represented by the general formula (I) or salts thereof have excellent effects as agricultural and horticultural herbicides.

[0011] In the definition of the general formula (I) of the compound of the present invention, "halo" means a "halogen atom", and is usually exemplified by a chlorine atom, a bromine atom, an iodine atom, or a fluorine atom.

[0012] "(C １ -C ６ The term "alkyl group" refers to a linear or branched alkyl group having 1 to 6 carbon atoms, such as a methyl group, an ethyl group, a normal propyl group, an isopropyl group, a normal butyl group, an isobutyl group, a secondary butyl group, a tertiary butyl group, a normal pentyl group, an isopentyl group, a tertiary pentyl group, a neopentyl group, a 2,3-dimethylpropyl group, a 1-ethylpropyl group, a 1-methylbutyl group, a 2-methylbutyl group, a normal hexyl group, an isohexyl group, a 2-hexyl group, a 3-hexyl group, a 2-methylpentyl group, a 3-methylpentyl group, a 1,1,2-trimethylpropyl group, or a 3,3-dimethylbutyl group.

[0013] "(C ２ -C ６ The term "(C )alkenyl group" refers to a linear or branched alkenyl group having 2 to 6 carbon atoms, such as a vinyl group, an allyl group, an isopropenyl group, a 1-butenyl group, a 2-butenyl group, a 2-methyl-2-propenyl group, a 1-methyl-2-propenyl group, a 2-methyl-1-propenyl group, a pentenyl group, a 1-hexenyl group, or a 3,3-dimethyl-1-butenyl group. ２ -C ６The term "alkynyl group" refers to a straight-chain or branched-chain alkynyl group having 2 to 6 carbon atoms, such as an ethynyl group, a 1-propynyl group, a 2-propynyl group, a 1-butynyl group, a 2-butynyl group, a 3-butynyl group, a 3-methyl-1-propynyl group, a 2-methyl-3-propynyl group, a pentynyl group, a 1-hexynyl group, a 3-methyl-1-butynyl group, or a 3,3-dimethyl-1-butynyl group.

[0014] "(C ３ -C ６ The term "cycloalkyl group" refers to a cyclic alkyl group having 3 to 6 carbon atoms, such as a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, or a cyclohexyl group.

[0015] "(C １ -C ６ The term "alkoxy group" refers to a linear or branched alkoxy group having 1 to 6 carbon atoms, such as a methoxy group, an ethoxy group, a normal propoxy group, an isopropoxy group, a normal butoxy group, a secondary butoxy group, a tertiary butoxy group, a normal pentyloxy group, an isopentyloxy group, a tertiary pentyloxy group, a neopentyloxy group, a 2,3-dimethylpropyloxy group, a 1-ethylpropyloxy group, a 1-methylbutyloxy group, a normal hexyloxy group, an isohexyloxy group, or a 1,1,2-trimethylpropyloxy group.

[0016] "(C １ -C ６ The term "alkylsulfanyl group" refers to a linear or branched alkylsulfanyl group having 1 to 6 carbon atoms, such as a methylthio group, an ethylthio group, a normal propylthio group, an isopropylthio group, a normal butylthio group, a secondary butylthio group, a tertiary butylthio group, a normal pentylthio group, an isopentylthio group, a tertiary pentylthio group, a neopentylthio group, a 2,3-dimethylpropylthio group, a 1-ethylpropylthio group, a 1-methylbutylthio group, a normal hexylthio group, an isohexylthio group, or a 1,1,2-trimethylpropylthio group.

[0017] "(C １ -C ６The term "alkylsulfinyl group" refers to a linear or branched alkylsulfinyl group having 1 to 6 carbon atoms, such as a methylsulfinyl group, an ethylsulfinyl group, a normal propylsulfinyl group, an isopropylsulfinyl group, a normal butylsulfinyl group, a secondary butylsulfinyl group, a tertiary butylsulfinyl group, a normal pentylsulfinyl group, an isopentylsulfinyl group, a tertiary pentylsulfinyl group, a neopentylsulfinyl group, a 2,3-dimethylpropylsulfinyl group, a 1-ethylpropylsulfinyl group, a 1-methylbutylsulfinyl group, a normal hexylsulfinyl group, an isohexylsulfinyl group, or a 1,1,2-trimethylpropylsulfinyl group.

[0018] "(C １ -C ６ The term "alkylsulfonyl group" refers to a linear or branched alkylsulfonyl group having 1 to 6 carbon atoms, such as a methylsulfonyl group, an ethylsulfonyl group, a normal propylsulfonyl group, an isopropylsulfonyl group, a normal butylsulfonyl group, a secondary butylsulfonyl group, a tertiary butylsulfonyl group, a normal pentylsulfonyl group, an isopentylsulfonyl group, a tertiary pentylsulfonyl group, a neopentylsulfonyl group, a 2,3-dimethylpropylsulfonyl group, a 1-ethylpropylsulfonyl group, a 1-methylbutylsulfonyl group, a normal hexylsulfonyl group, an isohexylsulfonyl group, or a 1,1,2-trimethylpropylsulfonyl group.

[0019] "(C １ -C ７ The term "(C) alkylcarbonyl group" refers to, for example, an acetyl group, a propanoyl group, a butanoyl group, a 2-methylpropanoyl group, a pentanoyl group, a 2-methylbutanoyl group, a 3-methylbutanoyl group, a pivaloyl group, a hexanoyl group, a heptanoyl group, an octanoyl group, or the like. １ -C ７ ) represents an alkylcarbonyl group having 2 to 8 carbon atoms, such as an alkylcarbonyl group having an alkyl group.

[0020] "(C １ -C ６The term "alkoxycarbonyl group" refers to, for example, a methoxycarbonyl group, an ethoxycarbonyl group, a normal propoxycarbonyl group, an isopropoxycarbonyl group, a normal butoxycarbonyl group, an isobutoxycarbonyl group, a secondary butoxycarbonyl group, a tertiary butoxycarbonyl group, a pentyloxycarbonyl group, or the like. １ -C ６ ) an alkoxycarbonyl group having 2 to 7 carbon atoms, such as an alkoxycarbonyl group having an alkoxy group.

[0021] The above "(C １ -C ６ ) alkyl group," "(C ２ -C ６ ) alkenyl group," "(C ２ -C ６ ) alkynyl group," "(C １ -C ６ ) alkoxy group," "(C １ -C ６ ) alkylsulfanyl group," "(C １ -C ６ ) alkylsulfinyl group," "(C １ -C ６ ) alkylsulfonyl group," "(C ３ -C ６ ) cycloalkyl group," "(C １ -C ６ ) alkylcarbonyl group," "(C １ -C ６ One or more halogen atoms may be substituted at substitutable positions of the "alkoxycarbonyl group" and the like, and when there are two or more halogen atoms substituted, the halogen atoms may be the same or different.

[0022] When substituted with a halogen atom, it is referred to as "halo(C １ -C ６ ) alkyl group," "halo(C ２ -C ６ ) alkenyl group," "halo(C ２ -C ６ ) alkynyl group," "halo(C １ -C ６ ) alkoxy group," "halo(C １ -C６ ) alkylsulfanyl group," "halo(C １ -C ６ ) alkylsulfinyl group," "halo(C １ -C ６ ) alkylsulfonyl group," "halo(C ３ -C ６ ) cycloalkyl group," "halo(C １ -C ６ ) alkylcarbonyl group," "halo(C １ -C ６ ) alkoxycarbonyl group" and the like.

[0023] In the present invention, "(C １ -C ６ )," "(C ２ -C ６ )," "(C ３ -C ６ Expressions such as "(C)" indicate the range of the number of carbon atoms of various substituents. Furthermore, the above definitions can also be applied to groups to which the above substituents are linked. For example, "(C １ -C ６ ) alkoxy(C １ -C ６ ) alkyl group" indicates that a linear or branched alkoxy group having 1 to 6 carbon atoms is bonded to a linear or branched alkyl group having 1 to 6 carbon atoms.

[0024] Examples of salts of the compound represented by general formula (I) of the present invention include inorganic acid salts such as hydrochloride, sulfate, nitrate, and phosphate; organic acid salts such as acetate, fumarate, maleate, oxalate, methanesulfonate, benzenesulfonate, and paratoluenesulfonate; and salts with inorganic or organic bases such as sodium ion, potassium ion, calcium ion, and trimethylammonium.

[0025] The compounds represented by general formula (I) of the present invention and salts thereof may have one or more asymmetric centers in their structural formulas, and may exist as two or more optical isomers and diastereomers, and the present invention encompasses all of the optical isomers and mixtures containing them in any ratio. Furthermore, the compounds represented by general formula (I) of the present invention and salts thereof may exist as two or more geometric isomers derived from a carbon-carbon double bond or a carbon-nitrogen double bond in their structural formulas, and the present invention encompasses all of the geometric isomers and mixtures containing them in any ratio. Furthermore, the compounds represented by general formula (I) of the present invention and salts thereof may exist as multiple tautomers, and the present invention encompasses all of the tautomers and mixtures containing them in any ratio.

[0026] In the compound of the present invention represented by general formula (I), preferred embodiments are shown below.

[0027] R １ As for (a1) (C １ -C ６ ) alkyl group; or (a3') N(R ２ａ ) R ２ｂ group (in the formula, R ２ａ and R ２ｂ are (b1) hydrogen atoms, (b2) (C １ -C ６ ) alkyl group, (b5) (C ３ -C ６ ) cycloalkyl group, (b6) halo (C １ -C ６ ) alkyl group, (b7) (C １ -C ７ ) alkylcarbonyl group, or (b8) (C １ -C ６ ) represents an alkoxycarbonyl group, and R ２ａ and R ２ｂ may be the same or different.) is preferred, and (a1) (C １ -C ６ ) alkyl group; or (a3'') N(R ２ａ ) R ２ｂ group (in the formula, R ２ａ and R ２ｂare (b1) hydrogen atoms, (b2) (C １ -C ６ ) alkyl group, (b7) (C １ -C ７ ) alkylcarbonyl group, or (b8) (C １ -C ６ ) represents an alkoxycarbonyl group, and R ２ａ and R ２ｂ may be the same or different.) is more preferred.

[0028] Het is preferably a group represented by formula (Het-1) or (Het-2).

[0029] R ３ (c1) a halogen atom, (c3) (C １ -C ６ ) alkyl group, (c4) (C ２ -C ６ ) alkenyl group, (c6) (C ３ -C ６ ) cycloalkyl group, (c7) (C １ -C ６ ) alkoxy group, (c8) halo (C １ -C ６ ) alkyl group, (c9) halo (C ２ -C ６ ) alkenyl group, (c11) halo (C ３ -C ６ ) cycloalkyl group, (c13) a substituted (C) group having 1 to 3 substituents independently selected from the substituent group S １ -C ６ ) alkyl group, (c14) a substituted (C) group having 1 to 3 substituents independently selected from the substituent group T ３ -C ６ ) cycloalkyl group, (c15) (C １ -C ６ ) alkylsulfanyl group, (c16) (C １ -C ６ ) alkylsulfinyl group, (c17) (C １ -C ６ ) alkylsulfonyl group, (c18) (C １ -C ６(c19) an alkoxycarbonyl group, (c20) a substituted furanyl group having 1 to 3 substituents independently selected from the substituent group U on the ring, (c23) a thienyl group, (c24) a substituted thienyl group having 1 to 3 substituents independently selected from the substituent group U on the ring, (c25) a thiazolyl group, (c26) a substituted thiazolyl group having 1 to 2 substituents independently selected from the substituent group U on the ring, (c27) a naphthyl group, (c28) a substituted naphthyl group having 1 to 7 substituents independently selected from the substituent group U on the ring, (c29) a phenyl group, (c30) a substituted phenyl group having 1 to 5 substituents independently selected from the substituent group U on the ring, (c31) a pyridyl group, (c32) a substituted pyridyl group having 1 to 4 substituents independently selected from the substituent group U on the ring, (c39) a phenyl (C １ -C ６ ) alkyl group, or (c40) a substituted phenyl (C １ -C ６ ) alkyl group is preferred, (c1) halogen atom, (c3) (C １ -C ６ ) alkyl group, (c4) (C ２ -C ６ ) alkenyl group, (c6) (C ３ -C ６ ) cycloalkyl group, (c8) halo (C １ -C ６ ) alkyl group (c13) a substituted (C) group having 1 to 3 substituents independently selected from the substituent group S １ -C ６ ) alkyl group, (c14) a substituted (C) group having 1 to 3 substituents independently selected from the substituent group T ３ -C ６ ) cycloalkyl group, (c18) (C １ -C ６) alkoxycarbonyl group, (c19) furanyl group, (c23) thienyl group, (c25) thiazolyl group, (c26) substituted thiazolyl group having 1 to 2 substituents independently selected from the substituent group U on the ring, (c27) naphthyl group, (c29) phenyl group, (c30) substituted phenyl group having 1 to 5 substituents independently selected from the substituent group U on the ring, (c31) pyridyl group, (c32) substituted pyridyl group having 1 to 4 substituents independently selected from the substituent group U on the ring, or (c40) substituted phenyl group having 1 to 5 substituents independently selected from the substituent group U on the ring (C １ -C ６ ) alkyl groups are more preferred.

[0030] Y is preferably a nitrogen atom or CH.

[0031] R ５ａ (d1) a hydrogen atom, or (d2) (C １ -C ６ ) alkyl groups are preferred, and (d2) (C １ -C ６ ) alkyl groups are more preferred.

[0032] R ５ｂ (e1) a hydrogen atom, or (e3) (C １ -C ６ ) Alkyl groups are preferred.

[0033] The substituent group S includes (f1) a cyano group, (f2) a (C ３ -C ６ ) cycloalkyl group, (f3) (C １ -C ６ ) alkoxy group, (f4) (C １ -C ６ ) alkylsulfanyl group, (f5) (C １ -C ６ ) alkylsulfinyl group, and (f6) (C １ -C ６ ) alkylsulfonyl group, (f3) (C １ -C ６ ) Alkoxy groups are more preferred.

[0034] The substituent group T includes (g1) a cyano group, (g2) a (C １ -C ６ ) alkyl group, (g8) halo (C １ -C ６ ) an alkyl group, and (g14) a phenyl group, and (g14) a phenyl group is more preferred.

[0035] The substituent group U includes (h1) a halogen atom, (h2) a cyano group, (h5) a hydroxyl group, (h6) a hydroxyl group (C １ -C ６ ) alkyl group, (h7) (C １ -C ６ ) alkyl group, (h10) (C ３ -C ６ ) cycloalkyl group, (h11) halo (C １ -C ６ ) alkyl group, (h14) halo (C ３ -C ６ ) cycloalkyl group, (h15) (C １ -C ６ ) alkoxy group, (h16) (C １ -C ６ ) alkylsulfanyl group, (h17) (C １ -C ６ ) alkylsulfinyl group, (h18) (C １ -C ６ ) alkylsulfonyl group, (h19) halo (C １ -C ６ ) alkoxy group, (h20) halo (C １ -C ６ ) alkylsulfanyl group, (h21) halo (C １ -C ６ ) alkylsulfinyl group, (h22) halo (C １ -C ６ ) alkylsulfonyl group, and (h23) N—((C １ -C ６ (h1) a halogen atom, (h5) a hydroxyl group, (h6) a hydroxy(C １ -C ６) alkyl group, (h7) (C １ -C ６ ) alkyl group, (h11) halo (C １ -C ６ ) alkyl groups, and (h15) (C １ -C ６ ) more preferably, it is an alkoxy group.

[0036] A includes (i1) an oxazolinyl group, (i2) a substituted oxazolinyl group having 1 to 4 substituents independently selected from substituent group V on the ring, (i3) an imidazolinyl group, (i4) a substituted imidazolinyl group having 1 to 4 substituents independently selected from substituent group V on the ring, (i5) an imidazolidinonyl group, (i6) a substituted imidazolidinonyl group having 1 to 4 substituents independently selected from substituent group V on the ring, (i7) a triazolinonyl group, (i8) a substituted triazolinonyl group having 1 to 2 substituents independently selected from substituent group V on the ring, (i9) a pyrazolinonyl group, (i10) a substituted pyrazolinonyl group having 1 to 3 substituents independently selected from substituent group V on the ring, (i11) a pyrazolyl group, (i12) (i13) a triazolyl group, (i14) a substituted triazolyl group having on the ring one to three substituents each independently selected from the substituent group V, (i21) a thiazolyl group, (i22) a substituted thiazolyl group having on the ring one to two substituents each independently selected from the substituent group V, (i23) an oxazolyl group, (i24) a substituted oxazolyl group having on the ring one to two substituents each independently selected from the substituent group V, (i25) tetrahydrofuranyl (C １ -C ６ ) alkoxy group, (i26) substituted tetrahydrofuranyl (C １ -C ６ ) alkoxy group, (i27) dioxolanyl (C １ -C ６) alkoxy group, (i28) substituted dioxolanyl (C １ -C ６ ) alkoxy group, (i29) isoxazolinyl (C １ -C ６ ) alkoxy group, (i30) substituted isoxazolinyl (C １ -C ６ ) alkoxy group, (i31) pyrazolyl (C １ -C ６ ) alkoxy group, (i32) substituted pyrazolyl (C １ -C ６ ) alkoxy group, (i33) triazolyl (C １ -C ６ ) alkoxy group, (i34) substituted triazolyl (C １ -C ６ ) alkoxy group, (i41) thiazolyl (C １ -C ６ ) alkoxy group, (i42) substituted thiazolyl (C １ -C ６ ) alkoxy group, (i43) oxazolyl (C １ -C ６ ) an alkoxy group, or (i44) a substituted oxazolyl (C １ -C ６(i10) a substituted pyrazolinonyl group having 1 to 3 substituents independently selected from the substituent group V on the ring; (i11) a pyrazolyl group; (i12) a substituted pyrazolyl group having 1 to 3 substituents independently selected from the substituent group V on the ring; (i13) a triazolyl group; (i14) a substituted pyrazolyl group having 1 to 3 substituents independently selected from the substituent group V on the ring; (i15) a substituted oxazolinyl group having 1 to 4 substituents independently selected from the substituent group V on the ring; (i16) a substituted imidazolidinonyl group having 1 to 4 substituents independently selected from the substituent group V on the ring; (i8) a substituted triazolinonyl group having 1 to 2 substituents independently selected from the substituent group V on the ring; (i10) a substituted pyrazolinonyl group having 1 to 3 substituents independently selected from the substituent group V on the ring; (i11) a pyrazolyl group; (i12) a substituted pyrazolyl group having 1 to 3 substituents independently selected from the substituent group V on the ring; (i13) a triazolyl group; (i14) (i22) a substituted triazolyl group having 1 to 2 substituents independently selected from the substituent group V on the ring; (i26) a substituted tetrahydrofuranyl group having 1 to 4 substituents independently selected from the substituent group V on the ring (C １ -C ６ ) alkoxy group, (i28) substituted dioxolanyl (C １ -C ６ ) alkoxy group, (i30) substituted isoxazolinyl (C １ -C ６ ) alkoxy group, (i31) pyrazolyl (C １ -C ６ ) alkoxy group, (i32) substituted pyrazolyl (C １ -C ６ ) alkoxy group, (i34) substituted triazolyl (C １ -C ６ ) alkoxy group, or (i42) substituted thiazolyl (C１ -C ６ ) Alkoxy groups are more preferred.

[0037] The substituent group V includes (j1) a halogen atom, (j2) a cyano group, (j3) a (C １ -C ６ ) alkyl group, (j4) (C ２ -C ６ ) alkenyl group, (j6) (C ３ -C ６ ) cycloalkyl group, (j7) halo (C １ -C ６ ) alkyl group, (j8) halo (C ２ -C ６ ) alkenyl group, (j10) halo (C ３ -C ６ ) cycloalkyl group, (j11) (C １ -C ６ ) alkoxy group, (j12) (C １ -C ６ ) alkylsulfanyl group, (j13) (C １ -C ６ ) alkylsulfinyl group, (j14) (C １ -C ６ ) alkylsulfonyl group, (j15) halo (C １ -C ６ ) alkoxy group, (j16) halo (C １ -C ６ ) alkylsulfanyl group, (j20) (C １ -C ６ ) alkylsulfanyl (C １ -C ６ ) alkyl group, (j21) (C １ -C ６ ) an alkoxycarbonyl group, (j22) a phenyl group, (j23) a halogen atom, (C １ -C ６ ) alkyl and halo(C １ -C ６ (j24) a substituted phenyl group having 1 to 5 substituents on the ring independently selected from the group consisting of alkyl, (j25) a thienyl group, and (j26) a halogen atom; １ -C ６ ) alkyl and halo(C１ -C ６ (j1) a halogen atom, (j3) a substituted thienyl group having 1 to 3 substituents independently selected from the group consisting of (C １ -C ６ ) alkyl group, (j4) (C ２ -C ６ ) alkenyl group, (j6) (C ３ -C ６ ) cycloalkyl group, (j7) halo (C １ -C ６ ) alkyl group, (j11) (C １ -C ６ ) alkoxy group, (j12) (C １ -C ６ ) alkylsulfanyl group, (j20) (C １ -C ６ ) alkylsulfanyl (C １ -C ６ ) alkyl group, (j21) (C １ -C ６ ) an alkoxycarbonyl group, (j23') a substituted phenyl group having from 1 to 5 substituents independently selected from halogen atoms on the ring, and (j24) a thienyl group.

[0038] The various compounds of the present invention can be produced, for example, by the following production methods, but the present invention is not limited to these.

[0039] Production Method 1 The compound of the present invention represented by general formula (I) can be produced from the compound of general formula (II-1) by the following step [a-1].

[0040] {wherein Het, R １ and A are the same as above. L is, for example, fluorine, chlorine, bromine, iodine, (C １ -C ４ ) alkylsulfonyl group, (C １ -C ４ ) alkylsulfonyloxy group, halo(C １ -C ４ ) represents a leaving group such as an alkylsulfonyloxy group.

[0041] Production Method in Step [a-1] The compound represented by general formula (I) of the present invention can be produced by reacting the compound represented by general formula (II-1) with the compound represented by general formula (III-1) in the presence of an inert solvent and in the presence or absence of a base.

[0042] Examples of the base that can be used in this reaction include inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, cesium carbonate, sodium hydrogencarbonate, potassium hydrogencarbonate, and sodium hydride; acetates such as sodium acetate and potassium acetate; alkali metal alkoxides such as potassium tert-butoxide, sodium methoxide, and sodium ethoxide; organic bases such as tertiary amines such as triethylamine, N,N-diisopropylethylamine, and DBU; nitrogen-containing aromatic compounds such as pyridine and N,N-dimethyl-4-aminopyridine; alkyllithiums such as methyllithium, normal butyllithium, secondary butyllithium, and tert-butyllithium; and organometallic compounds such as lithium hexamethyldisilazane and sodium hexamethyldisilazane. The amount of the base used is usually in the range of 1 to 10 times the moles of the compound represented by general formula (II-1).

[0043] The inert solvent that can be used in this reaction may be any solvent that does not significantly inhibit the progress of this reaction, and examples thereof include inert solvents such as linear or cyclic saturated hydrocarbons such as pentane, hexane, cyclohexane, etc.; aromatic hydrocarbons such as benzene, toluene, xylene, etc.; halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, etc.; halogenated aromatic hydrocarbons such as chlorobenzene, dichlorobenzene, etc.; linear or cyclic ethers such as diethyl ether, methyl tertiary butyl ether, dioxane, tetrahydrofuran, etc.; nitriles such as acetonitrile, propionitrile, etc.; esters such as methyl acetate, etc.; ketones such as acetone, methyl ethyl ketone, etc.; aprotic polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, dimethyl sulfoxide, 1,3-dimethyl-2-imidazolidinone, etc.; and alcohols such as methanol, ethanol, propanol, butanol, 2-propanol, etc. These inert solvents can be used alone or in combination. The amount used may be appropriately selected from the range of usually 0.1 L to 100 L per mole of the compound represented by general formula (II-1).

[0044] Since this reaction is an equimolar reaction, each compound may be used in equimolar amounts, although any compound may be used in excess. The reaction temperature in this reaction is typically within the range of 0°C to the boiling point of the solvent used, and the reaction time varies depending on the reaction scale, reaction temperature, etc., and is not constant, but may typically be selected appropriately within the range of several minutes to 48 hours. After completion of the reaction, the target product may be isolated from the reaction system containing the target product by conventional methods, and the target product can be produced by purifying it, if necessary, by recrystallization, column chromatography, or the like.

[0045] Production Method 2 The compound of the present invention represented by general formula (I') can be produced from the compound of general formula (II-1) by the following step [a-2].

[0046] where Het and R １A' is (i11) a pyrazolyl group, (i12) a substituted pyrazolyl group having on the ring 1 to 3 substituents each independently selected from the substituent group V, (i13) a triazolyl group, (i14) a substituted triazolyl group having on the ring 1 to 2 substituents each independently selected from the substituent group V, (i15) a tetrazolyl group, (i16) a substituted tetrazolyl group having on the ring 1 substituent selected from the substituent group V, (i17) an imidazolyl group, (i18) a substituted tetrazolyl group having on the ring 1 substituent each independently selected from the substituent group V L represents, for example, fluorine, chlorine, bromine, iodine, (C １ -C ４ ) alkylsulfonyl group, (C １ -C ４ ) alkylsulfonyloxy group, halo(C １ -C ４ ) represents a leaving group such as an alkylsulfonyloxy group.

[0047] Production Method in Step [a-2] The compound represented by general formula (I') of the present invention can be produced by reacting the compound represented by general formula (II-1) with a boronic acid represented by general formula (III-2) or its pinacol ester in the presence of a metal catalyst, a base and an inert solvent.

[0048] Examples of the base that can be used in this reaction include carbonates such as lithium carbonate, lithium hydrogencarbonate, sodium carbonate, potassium carbonate, cesium carbonate, potassium hydrogencarbonate, calcium carbonate, and magnesium carbonate; acetates such as lithium acetate, sodium acetate, and potassium acetate; and organic bases such as pyridine, picoline, lutidine, triethylamine, tributylamine, N,N-diisopropylethylamine, and 1,4-diazabicyclo[2.2.2]octane. The amount of the base that can be used is usually in the range of 1 to 5 times the moles of the compound represented by general formula (II-1).

[0049] Examples of metal catalysts that can be used in this reaction include palladium catalysts, nickel catalysts, iron catalysts, ruthenium catalysts, platinum catalysts, rhodium catalysts, and iridium catalysts. Examples of these metal catalysts that can be used include metals, supported metals, metal salts such as metal chlorides, bromides, iodides, nitrates, sulfates, carbonates, oxalates, acetates, and oxides, and complex compounds such as olefin complexes, phosphine complexes, amine complexes, ammine complexes, and acetylacetonate complexes.

[0050] Among metal catalysts, palladium catalysts are particularly preferred. Examples of palladium catalysts include palladium metal such as palladium black and palladium sponge; supported palladium metal such as palladium / alumina, palladium / carbon, palladium / silica, and palladium / Y-type zeolite; metal salts such as palladium chloride, palladium bromide, palladium iodide, and palladium acetate; π-allylpalladium chloride dimer, palladium acetylacetonate, dichlorobis(acetonitrile)palladium, dichlorobis(benzonitrile)palladium, bis(dibenzylideneacetone)palladium, tris(dibenzylideneacetone)dipalladium, tris(dibenzylideneacetone)dipalladium (chloroform adduct), dichlorodiaminepalladium, and di Examples of the metal catalyst include chlorobis(triphenylphosphine)palladium, dichlorobis(tricyclohexylphosphine)palladium, tetrakis(triphenylphosphine)palladium, dichloro[1,2-bis(diphenylphosphino)ethane]palladium, dichloro[1,3-bis(diphenylphosphino)propane]palladium, dichloro[1,4-bis(diphenylphosphino)butane]palladium, dichloro[1,1'-bis(diphenylphosphino)ferrocene]palladium, and complex compounds such as diphenylphosphinoferrocene dichloropalladium-dichloromethane complex. The amount of these metal catalysts used may be appropriately selected usually from a range of 0.001 to 0.5 times the molar amount of the compound represented by general formula (II-1).

[0051] These palladium catalysts may be used alone or in combination with a tertiary phosphine. Examples of tertiary phosphines that can be used include triphenylphosphine, trimethylphosphine, triethylphosphine, tributylphosphine, tri(tertiarybutyl)phosphine, tricyclohexylphosphine, tri-o-tolylphosphine, trioctylphosphine, 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene, 2-(ditertiarybutylphosphino)biphenyl, 2-(dicyclohexylphosphino)biphenyl, 1,2-bis(diphenylphosphino)ethane, 1,3 ... Examples of the tertiary phosphine include bis(diphenylphosphino)propane, 1,4-bis(diphenylphosphino)butane, 1,1'-bis(diphenylphosphino)ferrocene, (R)-(+)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl, (S)-(-)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl, and (±)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl. The amount of these tertiary phosphines used may be appropriately selected usually from the range of 0.5 to 10 times the molar amount of the metal catalyst.

[0052] The inert solvent that can be used in this reaction may be any solvent that does not significantly inhibit this reaction, and examples thereof include alcohols such as methanol, ethanol, propanol, butanol, and 2-propanol; linear or cyclic ethers such as diethyl ether, tetrahydrofuran, dioxane, and 1,2-dimethoxyethane; aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated hydrocarbons such as methylene chloride, chloroform, and carbon tetrachloride; halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene; nitriles such as acetonitrile; esters such as ethyl acetate; polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, dimethyl sulfoxide, and 1,3-dimethyl-2-imidazolidinone; and water. These inert solvents can be used alone or in combination. The amount of the inert solvent used is not particularly limited as long as it is an amount that can dissolve the reaction reagents, and can usually be selected appropriately from a range of 0.5 L to 100 L per mole of the compound represented by general formula (II-1).

[0053] Since this reaction is an equimolar reaction, equimolar amounts of each compound may be used, although any compound may also be used in excess. The reaction temperature in this reaction is typically within the range of room temperature to the boiling point of the solvent used. The reaction time varies depending on the reaction scale, reaction temperature, etc., but may be appropriately selected from the range of several minutes to 48 hours. This reaction can also be carried out under an inert gas atmosphere, such as nitrogen gas or argon gas. After completion of the reaction, the target product can be isolated from the reaction system containing the target product by conventional methods, and can be produced by purifying it, if necessary, by recrystallization, column chromatography, or the like.

[0054] The compound of the present invention represented by general formula (I-1) can be produced from a compound of general formula (II-2) and a compound of general formula (Het-2-H) by the following step [b-1]. The reaction conditions for step [b-1] are the same as those for step [a-1].

[0055] {In the formula, R １ , R ３ , R ５ｂ, A and Y are the same as above, but A may be the above-mentioned A'. L is, for example, fluorine, chlorine, bromine, iodine, (C １ -C ４ ) alkylsulfonyl group, (C １ -C ４ ) alkylsulfonyloxy group, halo(C １ -C ４ ) represents a leaving group such as an alkylsulfonyloxy group.

[0056] Production method 1 of starting material Among the compounds represented by general formula (II-1) which are starting materials in Production method 1, R １ is the N(R ２ａ ) R ２ｂ Het is the formula (Het-2), and L is (C １ -C ４ The compound represented by general formula (II-1-1), in which the alkylsulfonyl group is a methyl group, can be produced from the compound represented by general formula (IV-1) by the following steps [c-1], [c-2], [c-3], and [c-4]. The reaction conditions for step [c-3] are the same as those for step [a-1].

[0057] {In the formula, R ２ａ , R ２ｂ , R ３ , R ５ｂ and Y are the same as above. R is, for example, a (C １ -C ４ ) represents an alkyl group, and X represents a leaving group of a halogen atom such as fluorine, chlorine, bromine, or iodine.}

[0058] Production Method of Step [c-1] A compound represented by general formula (IV-3) can be produced by reacting a compound represented by general formula (IV-1) with a compound represented by general formula (IV-2) in the presence of an inert solvent and in the presence or absence of a base.

[0059] Examples of the base that can be used in this reaction include inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, cesium carbonate, sodium hydrogencarbonate, and potassium hydrogencarbonate; acetates such as sodium acetate and potassium acetate; alkali metal alkoxides such as potassium tert-butoxide, sodium methoxide, and sodium ethoxide; tertiary amines such as triethylamine, N,N-diisopropylethylamine, and DBU; and nitrogen-containing aromatic compounds such as pyridine and N,N-dimethyl-4-aminopyridine. The amount of the base used is usually in the range of 1 to 10 times the moles of the compound represented by general formula (IV-1).

[0060] The inert solvent that can be used in this reaction may be any solvent that does not significantly inhibit the progress of this reaction, and examples thereof include aromatic hydrocarbons such as benzene, toluene, xylene, etc.; halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, etc.; halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene; chain or cyclic ethers such as diethyl ether, methyl tert-butyl ether, dioxane, tetrahydrofuran, etc.; alcohols such as methanol, ethanol, propanol, isopropyl alcohol, etc.; amides such as N,N-dimethylformamide and N,N-dimethylacetamide, etc.; and polar solvents such as dimethyl sulfoxide and 1,3-dimethyl-2-imidazolidinone. These inert solvents can be used alone or in combination of two or more. The amount of the inert solvent used is not particularly limited as long as it is an amount that can dissolve the reaction reagents, and may generally be selected appropriately from the range of 0.5 L to 100 L per mole of the compound represented by general formula (IV-1).

[0061] Since this reaction is an equimolar reaction, it is sufficient to use equimolar amounts of each compound, but it is also possible to use an excess of one compound. The reaction temperature in this reaction is usually within the range of 0°C to the boiling point of the solvent used, and the reaction time varies depending on the reaction scale and reaction temperature, but may be within the range of several minutes to 48 hours. After completion of the reaction, the target product can be isolated from the reaction system containing the target product by conventional methods, and can be produced by purifying it, if necessary, by recrystallization, column chromatography, or the like. Alternatively, the target product can be used in the next step without isolation.

[0062] Production Method of Step [c-2] A compound represented by general formula (IV-5) can be produced by reacting a compound represented by general formula (IV-3) with a compound represented by general formula (IV-4) in the presence of a base and an inert solvent.

[0063] Examples of the base that can be used in this reaction include inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, cesium carbonate, sodium bicarbonate, and potassium bicarbonate; acetates such as sodium acetate and potassium acetate; alkali metal alkoxides such as potassium tert-butoxide, sodium methoxide, and sodium ethoxide; tertiary amines such as triethylamine, N,N-diisopropylethylamine, and DBU; and nitrogen-containing aromatic compounds such as pyridine and N,N-dimethyl-4-aminopyridine. The amount of the base used is usually in the range of 1 to 10 times the molar amount of the compound represented by general formula (IV-3). When an alkali salt of the compound represented by general formula (IV-4) is used, a base does not necessarily have to be used.

[0064] The inert solvent that can be used in this reaction may be any solvent that does not significantly inhibit the progress of this reaction, and examples thereof include aromatic hydrocarbons such as benzene, toluene, xylene, etc.; halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, etc.; halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene; linear or cyclic ethers such as diethyl ether, methyl tert-butyl ether, dioxane, tetrahydrofuran, etc.; esters such as ethyl acetate, etc.; amides such as N,N-dimethylformamide and N,N-dimethylacetamide, etc.; ketones such as acetone and methyl ethyl ketone, etc.; and polar solvents such as dimethyl sulfoxide and 1,3-dimethyl-2-imidazolidinone, etc. These inert solvents can be used alone or in combination of two or more. The amount of the inert solvent used is not particularly limited as long as it is an amount that can dissolve the reaction reagents, and may generally be selected appropriately from the range of 0.5 L to 100 L per mole of the compound represented by general formula (IV-3).

[0065] Since this reaction is an equimolar reaction, it is sufficient to use equimolar amounts of each compound, but it is also possible to use an excess of one compound. The reaction temperature in this reaction is usually in the range of -20°C to the boiling point of the solvent used, and the reaction time varies depending on the reaction scale and reaction temperature, but may be in the range of several minutes to 48 hours. After completion of the reaction, the target product can be isolated from the reaction system containing the target product by conventional methods, and can be produced by purifying it by recrystallization, column chromatography, etc. as necessary. Alternatively, the target product can be used in the next step without isolation.

[0066] Production Method of Step [c-4] A compound represented by general formula (II-1-1) can be produced by reacting a compound represented by general formula (IV-6) with an oxidizing agent in the presence of an inert solvent.

[0067] Examples of the oxidizing agent that can be used in this reaction include peroxides such as hydrogen peroxide, perbenzoic acid, and metachloroperbenzoic acid, and the amount used is usually in the range of 1 to 5 times the molar amount of the compound represented by general formula (IV-6).

[0068] The inert solvent that can be used in this reaction may be any solvent that does not significantly inhibit this reaction, and examples thereof include linear or cyclic ethers such as diethyl ether, tetrahydrofuran, dioxane, etc.; aromatic hydrocarbons such as benzene, toluene, xylene, etc.; halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, etc.; halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene, nitriles such as acetonitrile, esters such as ethyl acetate, organic acids such as formic acid and acetic acid, and polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, 1,3-dimethyl-2-imidazolidinone, water, etc. These inert solvents can be used alone or in combination of two or more. The amount of the inert solvent used is not particularly limited as long as it is an amount that can dissolve the reaction reagents, and may generally be selected appropriately from a range of 0.5 L to 100 L per mole of the compound represented by general formula (IV-6).

[0069] The reaction temperature in this reaction may generally be in the range of -10°C to the boiling point of the solvent used, and the reaction time varies depending on the reaction scale, reaction temperature, etc., and is not constant, but may generally be selected appropriately from the range of several minutes to 48 hours. After completion of the reaction, the target product may be isolated from the reaction system containing the target product by a conventional method, and can be produced by purifying it by recrystallization, column chromatography, etc. as necessary. Alternatively, the target product may be subjected to the next step without isolation.

[0070] Production Method 2 of Starting Materials Among the compounds represented by general formula (II-1) which are starting materials for Production Method 1 and Production Method 2, R １ is the N(R ２ａ ) R ２ｂ A compound represented by general formula (II-1-2), in which Het is the formula (Het-1) above, Y is a nitrogen atom, and L is a halogen atom such as fluorine, chlorine, bromine, or iodine, can be produced from a compound represented by general formula (V-1) by the following steps [d-1], [d-2], [d-3], [d-4], and [d-5]. The reaction conditions for step [d-1] are the same as those for step [c-2] above.

[0071] {In the formula, R ２ａ , R２ｂ , R ３ , and R ５ａ is the same as above. R is, for example, a (C １ -C ４ R' represents, for example, a (C ) alkyl group such as a tertiary butyl group. １ -C ４ ) represents an alkyl group or a hydrogen atom. X represents a leaving group of a halogen atom such as fluorine, chlorine, bromine, or iodine.

[0072] Preparation Method of Step [d-2] A compound represented by general formula (V-4) can be prepared by hydrolyzing a compound represented by general formula (V-3) in the presence of a base, water, and an inert solvent.

[0073] Examples of the base that can be used in this reaction include organic bases such as hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide, and calcium hydroxide, and the amount used thereof is usually in the range of 1 to 10 times the molar amount of the compound represented by general formula (V-3).

[0074] The inert solvent that can be used in this reaction may be any solvent that does not significantly inhibit this reaction, and examples thereof include non-polar solvents such as linear or cyclic saturated hydrocarbons such as pentane, hexane, cyclohexane, etc.; linear or cyclic ethers such as diethyl ether, tetrahydrofuran, dioxane, etc.; and aromatic hydrocarbons such as benzene, toluene, xylene, etc. These inert solvents can be used alone or in combination of two or more. The amount of the inert solvent used is not particularly limited as long as it is an amount that can dissolve the reaction reagents, and may usually be appropriately selected from the range of 0.5 L to 100 L per mole of the compound represented by general formula (V-3).

[0075] The reaction temperature in this reaction may generally be in the range of 0°C to the boiling point of the solvent used, and the reaction time varies depending on the reaction scale, reaction temperature, etc., and is not constant, but may be appropriately selected from the range of several minutes to 48 hours. After completion of the reaction, the target product may be isolated from the reaction system containing the target product by a conventional method, and can be produced by purifying it, if necessary, by recrystallization, column chromatography, etc. Alternatively, the target product may be subjected to the next step without isolation.

[0076] Production Method in Step [d-3] A compound represented by general formula (V-4) and a compound represented by general formula (V-5) are reacted in the presence of a base, a condensing agent, and an inert solvent to produce a compound represented by general formula (V-6).

[0077] Condensing agents that can be used in this condensation reaction include, for example, acid-activating reagents such as phosgene, phosphorus trichloride, phosphorus oxychloride, oxalyl chloride, and thionyl chloride; carbodiimides such as N,N'-dicyclohexylcarbodiimide (DCC) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (EDCI); and others such as phosphorus pentoxide, polyphosphoric acid, N,N'-carbonyldiimidazole, 2-chloropyridine 1-methiodide (Mukaiyama reagent), 2-ethoxy-N-ethoxycarbonyl-1,2-dihydroquinoline (EEDQ), triphenylphosphine / carbon tetrachloride, bromotripyrrolidinophosphonium hexafluorophosphate (BROP), O-(1H-benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate (BOP), N,N,N',N'-bis(tetramethylamino)phosphonium hexafluorophosphate, N,N,N',N'-bis(tetramethylamino)phosphonium hexafluorophosphate ... O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate (HBTU), O-(1H-benzotriazol-1-yl)-N,N,N',N'-bis(tetramethylene)uronium hexafluorophosphate, O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate (TBTU), O-(1H-benzotriazol-1-yl)-N,N,N',N'-bis(tetramethylene)uronium tetrafluoroborate, O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate (HATU), 1-hydroxybenzotriazole (HOBt), propylphosphonic anhydride (T ３ These reagents can be used alone or in combination of two or more. The amount of the condensing agent used can be appropriately selected usually from the range of 0.5 to 5 times the molar amount of the compound represented by general formula (V-4).

[0078] Examples of the base that can be used in this condensation reaction include carbonates such as lithium carbonate, lithium hydrogen carbonate, sodium carbonate, sodium hydrogen carbonate, potassium carbonate, cesium carbonate, potassium hydrogen carbonate, calcium carbonate, and magnesium carbonate; acetates such as lithium acetate, sodium acetate, and potassium acetate; and organic bases such as pyridine, picoline, lutidine, triethylamine, tributylamine, and N,N-diisopropylethylamine. The amount of the base used can be appropriately selected usually from a range of 0.5 to 5 times the moles of the compound represented by general formula (V-4), and the base can also be used as a solvent.

[0079] The inert solvent that can be used in this condensation reaction may be any solvent that does not significantly inhibit this reaction. Examples of the inert solvent include linear or cyclic saturated hydrocarbons such as pentane, hexane, and cyclohexane; linear or cyclic ethers such as diethyl ether, tetrahydrofuran, and dioxane; aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated hydrocarbons such as methylene chloride, chloroform, and carbon tetrachloride; nitriles such as acetonitrile and isopropylnitrile; and polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, dimethyl sulfoxide, and 1,3-dimethyl-2-imidazolidinone. These inert solvents can be used alone or in combination of two or more. The amount of the inert solvent used is not particularly limited as long as it is an amount that can dissolve the reaction reagents, and can usually be selected appropriately from a range of 0.5 L to 100 L per mole of the compound represented by general formula (V-4). Furthermore, when the base is used as a solvent, no solvent is required.

[0080] Since this condensation reaction is an equimolar reaction, each compound may be used in equimolar amounts, although any compound may be used in excess. The reaction temperature in this reaction is typically within the range of 0°C to the boiling point of the solvent used. The reaction time varies depending on the reaction scale, reaction temperature, etc., and is not constant, but is typically selected appropriately from a range of several minutes to 48 hours. After completion of the reaction, the target product may be isolated from the reaction system containing the target product by conventional methods, and can be produced by purifying it, if necessary, by recrystallization, column chromatography, or the like. Alternatively, the target product may be subjected to the next step without isolation.

[0081] Preparation Method of Step [d-4] A compound represented by general formula (V-8) can be prepared by reacting a compound represented by general formula (V-6) with a compound represented by general formula (V-7) or a salt thereof in the presence of an inert solvent and in the presence or absence of a base.

[0082] Examples of the base that can be used in this reaction include inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, cesium carbonate, sodium hydrogencarbonate, and potassium hydrogencarbonate; acetates such as sodium acetate and potassium acetate; alkali metal alkoxides such as potassium tert-butoxide, sodium methoxide, and sodium ethoxide; tertiary amines such as triethylamine, N,N-diisopropylethylamine, and DBU; nitrogen-containing aromatic compounds such as pyridine and N,N-dimethyl-4-aminopyridine; and the like. The amount of the base to be used is usually in the range of 1 to 10 times the moles of the compound represented by general formula (V-6).

[0083] The inert solvent that can be used in this reaction may be any solvent that does not significantly inhibit the progress of this reaction, and examples thereof include aromatic hydrocarbons such as benzene, toluene, xylene, etc.; halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, etc.; halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene; linear or cyclic ethers such as diethyl ether, methyl tert-butyl ether, dioxane, tetrahydrofuran, etc.; alcohols such as methanol, ethanol, propanol, isopropyl alcohol, etc.; esters such as ethyl acetate, etc.; amides such as N,N-dimethylformamide and N,N-dimethylacetamide, etc.; ketones such as acetone and methyl ethyl ketone, etc.; and polar solvents such as dimethyl sulfoxide and 1,3-dimethyl-2-imidazolidinone, etc. These inert solvents can be used alone or in combination of two or more. The amount of the inert solvent used is not particularly limited as long as it is an amount that can dissolve the reaction reagents, and may usually be appropriately selected from the range of 0.5 L to 100 L per mole of the compound represented by general formula (V-6).

[0084] Since this reaction is an equimolar reaction, it is sufficient to use equimolar amounts of each compound, but it is also possible to use an excess of one compound. The reaction temperature in this reaction is generally within the range of room temperature to the boiling point of the solvent used, and the reaction time varies depending on the reaction scale and reaction temperature, but may be within the range of several minutes to 48 hours. After completion of the reaction, the target product can be isolated from the reaction system containing the target product by conventional methods, and can be produced by purifying it by recrystallization, column chromatography, or the like, as necessary. Alternatively, the target product can be used in the next step without isolation.

[0085] Production Method in Step [d-5] A compound represented by general formula (V-8) is reacted with a halogenating agent in the presence of an inert solvent to be chlorosulfonylated, and then amination reaction with a compound represented by general formula (IV-2) in the presence of an inert solvent in the presence or absence of a base, to thereby produce a compound represented by general formula (II-1-2).

[0086] Examples of the halogenating agent that can be used in this chlorosulfonylation reaction include thionyl chloride, chlorine, sulfuryl chloride, 1,3-dichloro-5,5-dimethylhydantoin, and N-chlorosuccinimide. The amount of the halogenating agent may be appropriately selected usually in a range of 0.5 to 5 times by mole relative to the compound represented by general formula (V-8).

[0087] The inert solvent that can be used in this chlorosulfonylation reaction may be any solvent that does not significantly inhibit the progress of this reaction, and examples thereof include inert solvents such as halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, etc.; halogenated aromatic hydrocarbons such as chlorobenzene, dichlorobenzene, etc.; nitriles such as acetonitrile, propionitrile, etc.; organic acids such as acetic acid, propionic acid, etc.; water, etc. These inert solvents can be used alone or in combination of two or more. The amount of the inert solvent used is not particularly limited as long as it is an amount that can dissolve the reaction reagents, and may usually be appropriately selected from the range of 0.5 L to 100 L per mole of the compound represented by general formula (V-8).

[0088] Since this chlorosulfonylation reaction is an equimolar reaction, each compound may be used in equimolar amounts, although either compound may be used in excess. The reaction temperature in this reaction is typically within the range of room temperature to the boiling point of the solvent used. The reaction time varies depending on the reaction scale and reaction temperature, but may be within the range of several minutes to 48 hours. After completion of the reaction, if the chlorosulfonylated product is stable, it can be isolated from the reaction system containing the target product using standard methods, and can be purified by recrystallization, column chromatography, or the like, as needed. If the chlorosulfonylated product is unstable, the reaction system can be used directly in the next reaction without purification.

[0089] Examples of the base that can be used in this amination reaction include inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, cesium carbonate, sodium bicarbonate, and potassium bicarbonate; acetates such as sodium acetate and potassium acetate; alkali metal alkoxides such as potassium tert-butoxide, sodium methoxide, and sodium ethoxide; tertiary amines such as triethylamine, N,N-diisopropylethylamine, and DBU; and nitrogen-containing aromatic compounds such as pyridine and N,N-dimethyl-4-aminopyridine. The amount of the base used is usually in the range of 1 to 10 times the moles of the compound represented by general formula (V-8).

[0090] The inert solvent that can be used in this amination reaction may be any solvent that does not significantly inhibit the progress of this reaction, and examples thereof include aromatic hydrocarbons such as benzene, toluene, xylene, etc.; halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, etc.; halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene; linear or cyclic ethers such as diethyl ether, methyl tert-butyl ether, dioxane, tetrahydrofuran, etc.; alcohols such as methanol, ethanol, propanol, isopropyl alcohol, etc.; amides such as N,N-dimethylformamide and N,N-dimethylacetamide, etc.; and polar solvents such as dimethyl sulfoxide and 1,3-dimethyl-2-imidazolidinone, etc. These inert solvents can be used alone or in combination of two or more. The amount of the inert solvent to be used is not particularly limited as long as it is an amount that can dissolve the reaction reagents, and may usually be appropriately selected from a range of 0.5 L to 100 L per mole of the compound represented by general formula (V-8).

[0091] Since this amination reaction is an equimolar reaction, each compound may be used in equimolar amounts, although any compound may be used in excess. The reaction temperature in this reaction is typically within the range of 0°C to the boiling point of the solvent used, and the reaction time varies depending on the reaction scale and reaction temperature, but may be within the range of several minutes to 48 hours. After completion of the reaction, the target product can be isolated from the reaction system containing it by conventional methods, and can be purified by recrystallization, column chromatography, or the like, as necessary, to produce the target product.

[0092] Production Method 3 of Starting Materials Among the compounds represented by general formula (II-1) which are starting materials for Production Method 1 and Production Method 2, R １ is the N(R ２ａ ) R ２ｂ Het is the formula (Het-1), and Y is the formula (CR ４ and L is a halogen atom such as fluorine, chlorine, bromine, or iodine, can be produced from a compound represented by general formula (V-4) by the following steps [e-1], [e-2], [e-3], and [e-4]. The reaction conditions for step [e-4] are the same as those for step [d-5].

[0093] {In the formula, R ２ａ , R ２ｂ , R ３ , R ４ and R ５ａ is the same as above. R' is, for example, a (C １ -C ４ ) represents an alkyl group or a hydrogen atom. L′ and L may be the same or different, and are, for example, fluorine, chlorine, bromine, iodine, (C １ -C ４ ) represents a leaving group such as an alkylcarbonyloxy group, and X represents a leaving group of a halogen atom such as fluorine, chlorine, bromine, or iodine.

[0094] Production Method of Step [e-1] A compound represented by general formula (VI-2) can be produced by reacting a compound represented by general formula (V-4) with a compound represented by general formula (VI-1) in the presence of a base and an inert solvent.

[0095] Examples of the base that can be used in this reaction include inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, cesium carbonate, sodium hydrogencarbonate, and potassium hydrogencarbonate; acetates such as sodium acetate and potassium acetate; alkali metal alkoxides such as potassium tert-butoxide, sodium methoxide, and sodium ethoxide; tertiary amines such as triethylamine, N,N-diisopropylethylamine, and DBU; nitrogen-containing aromatic compounds such as pyridine and N,N-dimethyl-4-aminopyridine; and the like. The amount of the base to be used is usually in the range of 1 to 10 times the moles of the compound represented by general formula (V-4).

[0096] The inert solvent that can be used in this reaction may be any solvent that does not significantly inhibit the progress of this reaction, and examples thereof include aromatic hydrocarbons such as benzene, toluene, xylene, etc.; halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, etc.; halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene; linear or cyclic ethers such as diethyl ether, methyl tert-butyl ether, dioxane, tetrahydrofuran, etc.; esters such as ethyl acetate, etc.; amides such as N,N-dimethylformamide and N,N-dimethylacetamide, etc.; ketones such as acetone and methyl ethyl ketone, etc.; and polar solvents such as dimethyl sulfoxide and 1,3-dimethyl-2-imidazolidinone, etc. These inert solvents can be used alone or in combination of two or more. The amount of the inert solvent used is not particularly limited as long as it is an amount that can dissolve the reaction reagents, and may usually be appropriately selected from the range of 0.5 L to 100 L per mole of the compound represented by general formula (V-4).

[0097] Since this reaction is an equimolar reaction, it is sufficient to use equimolar amounts of each compound, but it is also possible to use an excess of one compound. The reaction temperature in this reaction is generally within the range of room temperature to the boiling point of the solvent used, and the reaction time varies depending on the reaction scale and reaction temperature, but may be within the range of several minutes to 48 hours. After completion of the reaction, the target product can be isolated from the reaction system containing the target product by conventional methods, and can be produced by purifying it by recrystallization, column chromatography, or the like, as necessary. Alternatively, the target product can be used in the next step without isolation.

[0098] Production Method in Step [e-2] A compound represented by general formula (VI-3) can be produced by reacting a compound represented by general formula (VI-2) with a nitrogen source in the presence of an acid and an inert solvent.

[0099] Examples of the nitrogen source that can be used in this reaction include ammonia, ammonium carbamate, ammonium acetate, and ammonium carbonate. The amount of the nitrogen source used may be appropriately selected usually from the range of 1 to 20 times the molar amount of the compound represented by general formula (VI-2).

[0100] Examples of the acid that can be used in this reaction include inorganic acids such as hydrochloric acid, sulfuric acid, nitric acid, etc.; organic acids such as formic acid, acetic acid, propionic acid, trifluoroacetic acid, benzoic acid, etc.; sulfonic acids such as methanesulfonic acid, trifluoromethanesulfonic acid, p-toluenesulfonic acid, etc.; phosphoric acid, etc., and the amount of the acid to be used may be appropriately selected usually from a range of 0.01 to 10 times the molar amount of the compound represented by general formula (VI-2), and the acid can also be used as a solvent.

[0101] The inert solvent that can be used in this dehydration reaction may be any solvent that does not significantly inhibit the progress of this reaction. Examples of inert solvents that can be used include aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated hydrocarbons such as methylene chloride, chloroform, and carbon tetrachloride; halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene; linear or cyclic ethers such as diethyl ether, methyl tert-butyl ether, dioxane, and tetrahydrofuran; esters such as ethyl acetate; amides such as N,N-dimethylformamide and N,N-dimethylacetamide; ketones such as acetone and methyl ethyl ketone; and polar solvents such as dimethyl sulfoxide and 1,3-dimethyl-2-imidazolidinone. These inert solvents can be used alone or in combination of two or more. The amount of the inert solvent used is not particularly limited as long as it is an amount that can dissolve the reaction reagents, and can usually be selected appropriately from a range of 0.5 L to 100 L per mole of the compound represented by general formula (VI-2) obtained by the condensation reaction. Furthermore, when the acid is used as the solvent, no solvent is required.

[0102] The reaction temperature in this dehydration reaction may generally be in the range of room temperature to the boiling point of the solvent used, and the reaction time varies depending on the reaction scale and reaction temperature, but may be appropriately selected from the range of several minutes to 48 hours. After completion of the reaction, the target product may be isolated from the reaction system containing the target product by conventional methods, and can be produced by purification, as necessary, by recrystallization, column chromatography, etc. Alternatively, the target product may be subjected to the next step without isolation.

[0103] Production Method in Step [e-3] A compound represented by general formula (VI-5) can be produced by reacting a compound represented by general formula (VI-3) with a compound represented by general formula (VI-4) in the presence of an inert solvent and a base.

[0104] Examples of the base that can be used in this reaction include inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, cesium carbonate, sodium hydrogencarbonate, potassium hydrogencarbonate, and sodium hydride; acetates such as sodium acetate and potassium acetate; alkali metal alkoxides such as potassium tert-butoxide, sodium methoxide, and sodium ethoxide; tertiary amines such as triethylamine, N,N-diisopropylethylamine, and DBU; and nitrogen-containing aromatic compounds such as pyridine and N,N-dimethyl-4-aminopyridine. The amount of the base used is usually in the range of 1 to 10 times the moles of the compound represented by general formula (VI-3).

[0105] The inert solvent that can be used in this reaction may be any solvent that does not significantly inhibit the progress of this reaction, and examples thereof include aromatic hydrocarbons such as benzene, toluene, xylene, etc.; halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, etc.; halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene; linear or cyclic ethers such as diethyl ether, methyl tert-butyl ether, dioxane, tetrahydrofuran, etc.; esters such as ethyl acetate, etc.; amides such as N,N-dimethylformamide and N,N-dimethylacetamide, etc.; ketones such as acetone and methyl ethyl ketone, etc.; and polar solvents such as dimethyl sulfoxide and 1,3-dimethyl-2-imidazolidinone, etc. These inert solvents can be used alone or in combination of two or more. The amount of the inert solvent used is not particularly limited as long as it is an amount that can dissolve the reaction reagents, and may usually be appropriately selected from the range of 0.5 L to 100 L per mole of the compound represented by general formula (VI-3).

[0106] Since this reaction is an equimolar reaction, equimolar amounts of each compound may be used, although any compound may also be used in excess. The reaction temperature in this reaction is typically within the range of room temperature to the boiling point of the solvent used. The reaction time varies depending on the reaction scale, reaction temperature, etc., and is not constant, but may typically be selected appropriately within the range of several minutes to 48 hours. After completion of the reaction, the target product may be isolated from the reaction system containing the target product by conventional methods, and can be produced by purifying it, if necessary, by recrystallization, column chromatography, or the like. Alternatively, the target product may be subjected to the next step without isolation.

[0107] Among the compounds represented by general formula (II-2) that are starting materials in Production Method 3, compounds represented by general formula (II-2-1) in which L is a halogen atom such as fluorine, chlorine, bromine, or iodine can be produced from a compound represented by general formula (VII-1) by the following step [f-1]. The reaction conditions for step [f-1] are the same as those for the above step [a-1].

[0108] {In the formula, R １ and A is the same as above. X represents a leaving group of a halogen atom such as fluorine, chlorine, bromine, or iodine.

[0109] Among the compounds represented by general formula (II-2), which are starting materials for Production Method 3, compounds represented by general formula (II-2-1') in which A is the above-mentioned A' and L is a halogen atom such as fluorine, chlorine, bromine, or iodine can be produced from compounds represented by general formula (VII-1) by the following step [f-2]. The reaction conditions for step [f-2] are the same as those for the above-mentioned step [a-2].

[0110] {In the formula, R １ and A' are the same as above. X represents a leaving group of a halogen atom such as fluorine, chlorine, bromine, or iodine.}

[0111] Production Method 6 of Starting Material The compound represented by the general formula (Het-2-H) of Production Method 3 can be produced, for example, by the method described in Heterocycles, 1983, 20, 1243-1246 and Organic Process Research & Development, 2004, 8, 28-32, or by appropriately modifying the method.

[0112] Method for producing starting material 7 Among the compounds represented by general formula (II-1-2), R ２ａ The compound represented by general formula (II-1-2-1), in which is a hydrogen atom, can be produced from the compound represented by general formula (VIII-1) by the following steps [g-1], [g-2], [g-3], and [g-4]. The reaction conditions for step [g-1] are the same as those for step [c-1].

[0113] {In the formula, R ２ｂ , R ３ , and R ５ａ is the same as above. R is, for example, a (C １ -C ４ ) represents an alkyl group, and X represents a leaving group of a halogen atom such as fluorine, chlorine, bromine, or iodine.}

[0114] Preparation method of step [g-2] A compound represented by general formula (VIII-4) can be prepared by reacting a compound represented by general formula (VIII-3) with a halogenating agent in the presence of an inert solvent.

[0115] Examples of the halogenating agent that can be used in this reaction include thionyl chloride, chlorine, bromine, sulfuryl chloride, 1,3-dichloro-5,5-dimethylhydantoin, N-chlorosuccinimide, 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate), and the like. The halogenating agent can be appropriately selected usually in a range of 0.5 to 5 times the molar amount of the compound represented by general formula (VIII-3).

[0116] The inert solvent that can be used in this reaction may be any solvent that does not significantly inhibit the progress of this reaction, and examples thereof include halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, etc., halogenated aromatic hydrocarbons such as chlorobenzene, dichlorobenzene, etc., nitriles such as acetonitrile, propionitrile, etc., organic acids such as acetic acid, propionic acid, etc., water, etc. These inert solvents can be used alone or in combination of two or more. The amount of the inert solvent used is not particularly limited as long as it is an amount that can dissolve the compound, and may usually be appropriately selected from the range of 0.5 L to 100 L per mole of the compound represented by general formula (VIII-3).

[0117] The reaction temperature in this reaction may generally be in the range of 0°C to the boiling point of the solvent used, and the reaction time varies depending on the reaction scale, reaction temperature, etc., and is not constant, but may be appropriately selected from the range of several minutes to 48 hours. After completion of the reaction, the target product may be isolated from the reaction system containing the target product by a conventional method, and can be produced by purifying it, if necessary, by recrystallization, column chromatography, etc. Alternatively, the target product may be subjected to the next step without isolation.

[0118] Preparation Method of Step [g-3] A compound represented by general formula (VIII-5) can be prepared by reacting a compound represented by general formula (VIII-4) with an oxidizing agent in the presence of an inert solvent.

[0119] Examples of the oxidizing agent that can be used in this reaction include peroxides such as hydrogen peroxide, perbenzoic acid, and metachloroperbenzoic acid, and the amount used is usually in the range of 1 to 5 times the molar amount of the compound represented by general formula (VIII-4).

[0120] The inert solvent that can be used in this reaction may be any solvent that does not significantly inhibit this reaction, and examples thereof include linear or cyclic ethers such as diethyl ether, tetrahydrofuran, dioxane, etc.; aromatic hydrocarbons such as benzene, toluene, xylene, etc.; halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, etc.; halogenated aromatic hydrocarbons such as chlorobenzene, dichlorobenzene, etc.; nitriles such as acetonitrile, esters such as ethyl acetate, organic acids such as formic acid, acetic acid, etc.; polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, 1,3-dimethyl-2-imidazolidinone, water, etc. These inert solvents can be used alone or in combination of two or more. The amount of the inert solvent used is not particularly limited as long as it is an amount that can dissolve the compound, and may usually be appropriately selected from the range of 0.5 L to 100 L per mole of the compound represented by general formula (VIII-4).

[0121] The reaction temperature in this reaction may generally be in the range of -10°C to the boiling point of the solvent used, and the reaction time varies depending on the reaction scale, reaction temperature, etc., and is not constant, but may generally be selected appropriately from the range of several minutes to 48 hours. After completion of the reaction, the target product may be isolated from the reaction system containing the target product by a conventional method, and can be produced by purifying it by recrystallization, column chromatography, etc. as necessary. Alternatively, the target product may be subjected to the next step without isolation.

[0122] Preparation Method of Step [g-4] A compound represented by general formula (II-1-2-1) can be prepared by reacting a compound represented by general formula (VIII-5) with a compound represented by general formula (VIII-6) or a salt thereof in the presence of a base and an inert solvent.

[0123] Examples of the base that can be used in this reaction include inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, cesium carbonate, sodium hydrogencarbonate, and potassium hydrogencarbonate; acetates such as sodium acetate and potassium acetate; alkali metal alkoxides such as potassium tert-butoxide, sodium methoxide, and sodium ethoxide; tertiary amines such as triethylamine, N,N-diisopropylethylamine, and DBU; nitrogen-containing aromatic compounds such as pyridine and N,N-dimethyl-4-aminopyridine; and the like. The amount of the base used is usually in the range of 1 to 10 times the molar amount of the compound represented by general formula (VIII-5).

[0124] The inert solvent that can be used in this reaction may be any solvent that does not significantly inhibit the progress of this reaction, and examples thereof include aromatic hydrocarbons such as benzene, toluene, xylene, etc.; halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, etc.; halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene; linear or cyclic ethers such as diethyl ether, methyl tert-butyl ether, dioxane, tetrahydrofuran, etc.; alcohols such as methanol, ethanol, propanol, isopropyl alcohol, etc.; esters such as ethyl acetate, etc.; amides such as N,N-dimethylformamide, N,N-dimethylacetamide, etc.; ketones such as acetone and methyl ethyl ketone, etc.; polar solvents such as dimethyl sulfoxide, 1,3-dimethyl-2-imidazolidinone, acetic acid, etc. These inert solvents can be used alone or in combination of two or more. The amount of the inert solvent used is not particularly limited as long as it is an amount that can dissolve the compound, and may usually be selected appropriately from the range of 0.5 L to 100 L per mole of the compound represented by general formula (VIII-5).

[0125] Since this reaction is an equimolar reaction, it is sufficient to use equimolar amounts of each compound, but it is also possible to use an excess of one compound. The reaction temperature in this reaction is generally within the range of room temperature to the boiling point of the solvent used, and the reaction time varies depending on the reaction scale and reaction temperature, but may be within the range of several minutes to 48 hours. After completion of the reaction, the target product can be isolated from the reaction system containing the target product by conventional methods, and can be produced by purifying it by recrystallization, column chromatography, or the like, as necessary. Alternatively, the target product can be used in the next step without isolation.

[0126] Method 8 for Producing Starting Materials The compound represented by general formula (VIII-5) can also be produced from the compound represented by general formula (VIII-3) by the following steps [h-1] and [h-2].

[0127] {In the formula, R ２ｂ is the same as above. R is, for example, a (C １ -C ４ ) represents an alkyl group, and X represents a leaving group of a halogen atom such as fluorine, chlorine, bromine, or iodine.}

[0128] Production Method in Step [h-1] A compound represented by general formula (VIII-7) can be produced by reacting a compound represented by general formula (VIII-3) with a halogenating agent in the presence of water and an inert solvent.

[0129] The amount of water used in this reaction may be appropriately selected usually from the range of 0.5 to 10 times the moles of the compound represented by formula (VIII-3).

[0130] Examples of the halogenating agent that can be used in this reaction include thionyl chloride, chlorine, bromine, sulfuryl chloride, 1,3-dichloro-5,5-dimethylhydantoin, and N-chlorosuccinimide. The halogenating agent may be appropriately selected usually in a range of 0.5 to 5 times the molar amount of the compound represented by general formula (VIII-3).

[0131] The inert solvent that can be used in this reaction may be any solvent that does not significantly inhibit the progress of this reaction, and examples thereof include halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, etc.; halogenated aromatic hydrocarbons such as chlorobenzene, dichlorobenzene, etc.; nitriles such as acetonitrile, propionitrile, etc.; and organic acids such as acetic acid, propionic acid, etc. These inert solvents can be used alone or in combination of two or more. The amount of the inert solvent used is not particularly limited as long as it is an amount that can dissolve the compound, and may usually be appropriately selected from the range of 0.5 L to 100 L per mole of the compound represented by general formula (VIII-3).

[0132] The reaction temperature in this reaction may generally be in the range of 0°C to the boiling point of the solvent used, and the reaction time varies depending on the reaction scale, reaction temperature, etc., and is not constant, but may be appropriately selected from the range of several minutes to 48 hours. After completion of the reaction, the target product may be isolated from the reaction system containing the target product by a conventional method, and can be produced by purifying it, if necessary, by recrystallization, column chromatography, etc. Alternatively, the target product may be subjected to the next step without isolation.

[0133] Production Method in Step [h-2] A compound represented by general formula (VIII-5) can be produced by reacting a compound represented by general formula (VIII-7) with a halogenating agent in the presence of an inert solvent.

[0134] Examples of halogenating agents that can be used in this reaction include carbonyl halide compounds such as oxalyl chloride, phosgene, diphosgene, and triphosgene; sulfur halide compounds such as thionyl chloride and thionyl bromide; and phosphorus halide compounds such as phosphorus oxychloride, phosphorus oxybromide, phosphorus trichloride, phosphorus tribromide, and phosphorus pentachloride. These halogenating agents can be used alone or in combination of two or more. The amount of halogenating agent used may be appropriately selected from a range of 0.5 to 10 times the molar amount of the compound represented by general formula (VIII-7). The halogenating agent itself can also be used as a solvent. Furthermore, a catalyst such as N,N-dimethylformamide, which is generally known to promote halogenation reactions, can also be used.

[0135] The inert solvent that can be used in this reaction may be any solvent that does not significantly inhibit the progress of this reaction, and examples thereof include aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated hydrocarbons such as methylene chloride, chloroform, and carbon tetrachloride; and halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene. These inert solvents can be used alone or in combination of two or more. The amount of the inert solvent used is not particularly limited as long as it is an amount that can dissolve the compound, and is usually selected appropriately from the range of 0.5 L to 100 L per mole of the compound represented by general formula (VIII-7). Furthermore, when the halogenating agent itself is used as the solvent, no inert solvent is used.

[0136] The reaction temperature in this reaction may generally be in the range of 0°C to the boiling point of the solvent used, and the reaction time varies depending on the reaction scale, reaction temperature, etc., and is not constant, but may be appropriately selected from the range of several minutes to 48 hours. After completion of the reaction, the target product may be isolated from the reaction system containing the target product by a conventional method, and can be produced by purifying it, if necessary, by recrystallization, column chromatography, etc. Alternatively, the target product may be subjected to the next step without isolation.

[0137]

[0099] The compound represented by general formula (VIII-6) can be produced from the compound represented by general formula (IX-1) by the following step [i-1], or from the compound represented by general formula (IX-2) by the following steps [i-2] and [i-1]. Alternatively, the compound can be produced by the method described in WO 2006 / 018725 or by appropriately modifying the method.

[0138] {In the formula, R ３ and R ５ａ is the same as above. R is, for example, a (C １ -C ４ ) represents an alkyl group.

[0139] Production Method in Step [i-1] A compound represented by general formula (IX-1) or a salt thereof represented by general formula (IX-4) described later, or a salt thereof, can be reacted with a compound represented by general formula (V-7) or a salt thereof in the presence of an inert solvent to produce a compound represented by general formula (VIII-6) or a salt thereof.

[0140] The inert solvent that can be used in this reaction may be any solvent that does not significantly inhibit the progress of this reaction, and examples thereof include aromatic hydrocarbons such as benzene, toluene, xylene, etc.; halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, etc.; halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene; linear or cyclic ethers such as diethyl ether, methyl tertiary butyl ether, dioxane, tetrahydrofuran, etc.; alcohols such as methanol, ethanol, propanol, isopropyl alcohol, etc.; esters such as ethyl acetate, etc.; amides such as N,N-dimethylformamide and N,N-dimethylacetamide, etc.; ketones such as acetone and methyl ethyl ketone, etc.; polar solvents such as dimethyl sulfoxide and 1,3-dimethyl-2-imidazolidinone, etc. These inert solvents can be used alone or in combination of two or more. The amount of the inert solvent used is not particularly limited as long as it is an amount that can dissolve the compound, and may be appropriately selected from the range of usually 0.5 L to 100 L per mole of the compound represented by general formula (IX-1) or general formula (IX-4) described below.

[0141] Since this reaction is an equimolar reaction, each compound may be used in equimolar amounts, although any compound may be used in excess. The reaction temperature in this reaction is typically within the range of 0°C to the boiling point of the solvent used. The reaction time varies depending on the reaction scale, reaction temperature, etc., and is not constant, but may be appropriately selected from the range of several minutes to 48 hours. After completion of the reaction, the target product may be isolated from the reaction system containing the target product by conventional methods, and can be produced by purifying it, if necessary, by recrystallization, column chromatography, or the like. Alternatively, the target product may be subjected to the next step without isolation.

[0142] Production Method in Step [i-2] A compound represented by general formula (IX-2) is reacted with a compound represented by general formula (IX-3) in the presence of acetyl chloride and an inert solvent to produce a compound represented by general formula (IX-4) or a salt thereof.

[0143] The amount of acetyl chloride used in this reaction may be appropriately selected from the range of 0.5 to 10 times the molar amount of the compound represented by formula (IX-2).

[0144] The inert solvent that can be used in this reaction may be any solvent that does not significantly inhibit the progress of this reaction, and examples thereof include aromatic hydrocarbons such as benzene, toluene, xylene, etc.; halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, etc.; halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene; linear or cyclic ethers such as diethyl ether, methyl tert-butyl ether, dioxane, tetrahydrofuran, etc.; alcohols such as methanol, ethanol, propanol, isopropyl alcohol, etc.; esters such as ethyl acetate, etc.; amides such as N,N-dimethylformamide and N,N-dimethylacetamide, etc.; ketones such as acetone and methyl ethyl ketone, etc.; polar solvents such as dimethyl sulfoxide and 1,3-dimethyl-2-imidazolidinone, etc. These inert solvents can be used alone or in combination of two or more. The amount of the inert solvent used is not particularly limited as long as it is an amount that can dissolve the compound, and may generally be selected appropriately from the range of 0.5 L to 100 L per mole of the compound represented by general formula (IX-2). When the compound represented by formula (IX-3) itself is used as a solvent, an inert solvent does not need to be used.

[0145] Since this reaction is an equimolar reaction, each compound may be used in equimolar amounts, although any compound may be used in excess. The reaction temperature in this reaction is typically within the range of 0°C to the boiling point of the solvent used. The reaction time varies depending on the reaction scale, reaction temperature, etc., and is not constant, but may be appropriately selected from the range of several minutes to 48 hours. After completion of the reaction, the target product may be isolated from the reaction system containing the target product by conventional methods, and can be produced by purifying it, if necessary, by recrystallization, column chromatography, or the like. Alternatively, the target product may be subjected to the next step without isolation.

[0146] Representative examples of the compound represented by general formula (I) of the present invention are shown below in Tables 1 to 3, but the present invention is not limited to these. In the tables below, Me represents a methyl group, Et represents an ethyl group, i-Pr represents an isopropyl group, n-Pr represents a normal propyl group, c-Pr represents a cyclopropyl group, i-Bu represents an isobutyl group, n-Bu represents a normal butyl group, t-Bu represents a tertiary butyl group, n-Pen represents a normal pentyl group, c-Pen represents a cyclopentyl group, c-Hex represents a cyclohexyl group, n-Hep represents a normal heptyl group, Ac represents an acetyl group, Ph represents a phenyl group, and Bn represents a benzyl group. Physical properties are expressed as melting point (°C) or １ H-NMR is shown. １ The H-NMR data is shown in Table 4.

[0147]

[0148]

[0149]

[0150]

[0151]

[0152]

[0153]

[0154]

[0155]

[0156]

[0157]

[0158] Table 2 (continued)

[0159]

[0160]

[0161]

[0162]

[0163]

[0164]

[0165]

[0166]

[0167]

[0168]

[0169]

[0170]

[0171]

[0172]

[0173]

[0174]

[0175]

[0176]

[0177] Agricultural and horticultural herbicides containing the compound represented by general formula (I) of the present invention or a salt thereof as an active ingredient are excellent in environmental safety, such as physical properties suitable for various labor-saving application methods, systemic activity, and appropriate soil persistence, etc. Furthermore, agricultural and horticultural herbicides containing the compound represented by general formula (I) of the present invention or a salt thereof as an active ingredient are excellent in safety to animals including humans.

[0178] Useful plants for which the compound represented by general formula (I) of the present invention or a salt thereof can be used are not particularly limited, and examples thereof include cereals (rice, barley, wheat, rye, oats, corn, etc.), beans (soybean, adzuki bean, broad bean, pea, kidney bean, peanut, etc.), fruit trees and fruits (apple, citrus fruit, pear, grape, peach, plum, cherry, walnut, chestnut, almond, banana, etc.), leafy vegetables (cabbage, tomato, spinach, broccoli, lettuce, onion, green onion (chives, scallions), bell pepper, eggplant, strawberry, pepper, okra, chive, etc.), root vegetables (carrot, potato, sweet potato, taro, daikon radish, turnip, lotus root, burdock, garlic, etc.), and the like. Examples of plants that can be used include: crops for processing (cotton, hemp, beets, hops, sugarcane, sugar beets, olives, rubber, coffee, tobacco, tea, etc.), gourds (pumpkin, cucumber, watermelon, Sakhalin gourd, melon, etc.), pasture grasses (orchard grass, sorghum, timothy, clover, alfalfa, etc.), turfgrass (Korean grass, bentgrass, etc.), ornamental crops for perfumes and the like (lavender, rosemary, thyme, parsley, pepper, ginger, etc.), flowers (chrysanthemum, rose, carnation, orchid, tulip, lily, etc.), garden trees (ginkgo, cherry trees, Japanese maple, etc.), and forest trees (abies firs, spruces, pines, hiba, cedar, cypress, eucalyptus, etc.).

[0179] The above-mentioned "plant" also includes plants to which tolerance has been imparted by classical breeding methods or genetic engineering techniques to HPPD inhibitors such as isoxaflutole, ALS inhibitors such as imazethapyr and thifensulfuron-methyl, EPSP synthase inhibitors such as glyphosate, glutamine synthase inhibitors such as glufosinate, acetyl-CoA carboxylase inhibitors such as sethoxydim, and herbicides such as bromoxynil, dicamba and 2,4-D.

[0180] Examples of "plants" that have been conferred resistance by classical breeding methods include rapeseed, wheat, sunflower, and rice that are resistant to imidazolinone ALS-inhibiting herbicides such as imazethapyr. Rice is already sold under the trade name Clearfield (registered trademark). Similarly, soybeans that have been conferred resistance to sulfonylurea ALS-inhibiting herbicides such as thifensulfuron methyl by classical breeding methods are already sold under the trade name STS soybean. Similarly, examples of plants that have been conferred resistance to acetyl-CoA carboxylase inhibitors such as trione oxime and aryloxyphenoxypropionic acid herbicides by classical breeding methods include SR corn.

[0181] Plants to which resistance to acetyl-CoA carboxylase inhibitors has been imparted are described in Proceedings of the National Academy of Sciences of the United States of America (Proc. Natl. Acad. Sci. USA), Vol. 87, pp. 7175-7179 (1990), and elsewhere. Furthermore, mutant acetyl-CoA carboxylases resistant to acetyl-CoA carboxylase inhibitors have been reported in Weed Science, Vol. 53, pp. 728-746 (2005), and plants resistant to acetyl-CoA carboxylase inhibitors can be produced by introducing such mutant acetyl-CoA carboxylase genes into plants by genetic engineering techniques or by introducing a mutation related to conferring resistance into plant acetyl-CoA carboxylase. Furthermore, chimeraplasty techniques (Gura T. 1999. Repairing the Genome's Spelling Mistakes. Science 285: By introducing a nucleic acid with a base substitution mutation, such as those represented by the general formula (I) of the present invention, into plant cells to introduce site-specific amino acid substitution mutations into the plant's acetyl-CoA carboxylase gene, ALS gene, or the like, it is possible to produce plants that are resistant to acetyl-CoA carboxylase inhibitors, ALS inhibitors, or the like, and the compound represented by the general formula (I) of the present invention or a salt thereof can be used on these plants as well. The compound represented by the general formula (I) of the present invention does not harm these useful plants.

[0182] Further examples of toxins that can be expressed in genetically modified plants include insecticidal proteins from Bacillus cereus and Bacillus popiliae; δ-endotoxins such as Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C from Bacillus thuringiensis, insecticidal proteins such as VIP1, VIP2, VIP3 or VIP3A; insecticidal proteins from nematodes; toxins produced by animals such as scorpion toxins, spider toxins, wasp toxins or insect-specific neurotoxins; fungal toxins; plant lectins; agglutinins; trypsin inhibitors, serine protease inhibitors, patatin, cystatin, etc. ribosome-inactivating proteins (RIPs) such as ricin, corn-RIP, abrin, rufin, saporin, and bryodin; steroid metabolic enzymes such as 3-hydroxysteroid oxidase, ecdysteroid-UDP-glucosyltransferase, and cholesterol oxidase; ecdysone inhibitors; HMG-CoA reductase; ion channel inhibitors such as sodium channel and calcium channel inhibitors; juvenile hormone esterase; diuretic hormone receptor; stilbene synthase; bibenzyl synthase; chitinase; and glucanase.

[0183] Toxins expressed in such genetically modified plants also include hybrid toxins, truncated toxins, and modified toxins of δ-endotoxin proteins such as Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1, Cry9C, Cry34Ab, or Cry35Ab, and insecticidal proteins such as VIP1, VIP2, VIP3, or VIP3A. Hybrid toxins are produced using recombinant technology by combining different domains of these proteins in new ways. A known example of a truncated toxin is Cry1Ab, which lacks a portion of its amino acid sequence. Modified toxins have one or more amino acids substituted in the native toxin. Examples of these toxins and recombinant plants capable of synthesizing these toxins are described in EP 0374753, WO 93 / 07278, WO 95 / 34656, EP 0427529, EP 0451878, WO 03 / 052073, etc.

[0184] The toxins contained in these recombinant plants confer resistance to Coleoptera, Hemiptera, Diptera, Lepidoptera, and nematodes, among others. The agricultural and horticultural herbicides of the present invention can be used in combination with or as a system with these technologies.

[0185] Weeds that can be controlled by the compound represented by general formula (I) of the present invention or a salt thereof include dicotyledonous weeds such as morning glory (Ipomoea), Lindernia (Lindernia), Sesbania (Sesbania), Abutilon (Abutilon), Chamomile (Matricaria), Rorippa (Rorippa), Nettle (Urtica), Dead nettle (Lamium), Cocklebur (Xanthium), Mustard (Sinapis), Rotala, Veronica, Poppy (Papaver), Chenopodium (Chenopodium), White clover (Trifolium), Purslane (Portulaca), and Violet Pansy (Violet Pansy). la), common morning glory (Pharbitis), Chinese morning glory (Galeopsis), Datura, eggplant (Solanum), shepherd's purse (Capsella), thistle (Cirsium), sonchus (Sonchus), Galinsoga, chickweed (Stellaria), Senecio, Amaranthus, ragweed (Ambrosia), Kochia, Lamium, shepherd's purse (Leipidium), willow (Polygonum), cleaver (Galium), cornflower (Centaurea), mugwort (Artemisia), etc.

[0186] Monocotyledonous weed genera include Leptochloa, Phleum, Poa, Bolboschoenus, Festuca, Setaria, Eleusine, Sagittaria, Agropyron, Ischaemum, Cyperus, and Avena. , Bromus, Panicum, Cynodon, Monochoria, Alopecurus, Paspalum, Commelina, Fimbristylis, Lolium, Brachiaria, Agrostis, Eleocharis, Echinochloa esculenta, Scirpus, Schoenoplectus, Digitaria, Sorghum, and the like.

[0187] Specific examples of other weeds include Spirogyra, Amaranthus retroflexus, Amaranthus viridis, Setaria faberi, Leersia japonica, Leptochloa chinensis, Lindernia angustifolia, Lindernia procumbens, Dopatrium junceum, Ipomoea hederacea, Lindernia dubia, Sida spinosa, Polygonum pensylvanicum, Sesbania exaltata, Geranium carolinense, and Chenopodium ambrosioides, ragweed (Conyza bonariensis), foxtail (Setaria italica), burlap ragweed (Amaranthus powellii), knotweed (Polygonum cuspidatum), velvetleaf (Abutilon theophrasti), chamomile (Matricaria perforata), Japanese knotweed (Polygonum longisetum), persimmon (Veronica polita), barnyard grass (Echinochloa crus-galli), black-eyed jasmine (Amaranthus lividus), nightshade (Solanum nigrum), night burdock (Schoenoplectus juncoides (Roxb.) Palla), barnyard grass (Bromus catharticus), warbler (Murdannia keisak), and float clubweed (Bolboschoenus fluviatilis), Floating Crab (Scirpus maritimus), Bromus tectorum, Sagittaria pygmaea Miq, Rumex obtusifolius, Leersiaoryzoides (L.) Sw.), green foxtail (Setaria viridis), sickleweed (Cassia obtusifolia), giant ragweed (Conyza sumatrensis), common persian greens (Veronica persica), duckweed (Spirodela polyrhiza), cocklebur (Xanthium canadens), goldenrod (Coreopsis lanceolata), common morning glory (Panicum dichotomiflorum), giant milkweed (Asclepias syriaca), celery (Euphorbia maculata), plantain (Plantago asiatica), common red snapper (Rudbeckia laciniata), common amaranthus (Amaranthus palmeri), oats (Avena sativa), cocklebur (Xanthium strumarium, wild oat (Avena sterilis), goosegrass (Eleusine indica), arrowhead (Sagittaria trifolia), Dutch buttercup (Erodium cicutarium), Dutch earwort (Cerastium glomeratum), Oriental daisy (Matricaria matricarioides), chamomile (Matricaria chamomilla), vetch (Vicia angustifolia), vetch (Bromus secalinus), wild oat (Avena fatua), Japanese knotweed (Rotala indica Koehne), Rumex japonicus, Japanese knotweed (Paspalum distichum), foxglove (Bromus remotiflorus), yellow nutsedge (Cyperus esculentus), and burdock (Galium kinuta), Setaria glauca, Pueraria lobata, Eleocharis kuroguwai Ohwi, Sagittaria trifolia Caerulea, Ambrosia trifida, Hydrillaverticillata), Siberian clubweed (Bolboschoenus maritimus (L.) Palla), Corn marigold (Chrysanthemum segetum), Japanese sedge (Cyperus iria), Monochoria vaginalis, Echinochloa colona, ​​Japanese sedge (Alisma plantago-aquatica), Weedy rice (Oryza sativa), Polygonum lapathifolium, Finger millet (Eleusine coracana), Siberian sedge (Schoenoplectus nipponicus), Siberian sedge (Cyperus malaccensis), Quackgrass (Agropyron repens), Shattercane (Sorghum vulgare), Silky bentgrass (Apera spica-venti), Chenopodium album, white clover (Trifolium repens), white morning glory (Datura stramonium), horsetail (Equisetum arvense), annual bluegrass (Poa annua), annual bromegrass (Bromus japonicus), annual foxtail (Alopecurus aequalis), purslane (Portulaca oleracea), goldenrod (Solidago altissima), common sorghum (Sorghum halepense), common mustard (Brassica juncea), common dandelion (Taraxacum officinale), common bindweed (Convolvulus arvensis), water parsley (Oenanthe javanica), bindweed (Polygonum convolvulus), barnyardgrass (Echinochloa oryzicola Vasing, Taiwan ivy (Ischaemum rugosum), Veronica arvensis, Cyperus difformis L., Amaranthus rudis, Timothy (Phleumpratense, Clove Polygonum (Ludwigia prostrata Roxburgh), Dayflower (Commelina communis), Texas Panicum (Panicum texanum), Spurge (Euphorbia helioscopia), Spotted Tit (Festuca parvigluma), Rumex crispus, Shepherd's Purse (Capsella bursa-pastoris), Calendula (Euphorbia pseudochamaesyce), Heart Millet (Brachiaria plantaginea), Lolium multiflorum, Field Thistle (Cirsium japonicum), Black-legged Foxtail (Alopecurus myosuroides), Field Mustard (Sinapis arvensis), Groundnut (Senecio vulgaris), and Galinsoga ciliata, Amaranthus tricolor, Chickweed (Stellaria media), Papyrus (Cyperus papyrus), Cyperus rotundus, Amaranthus spinosus, Polygonum persicaria, Senecio cannabifolius, Cyperus flaccidus, Corn poppy (Papaver rhoeas), Sunflower (Helianthus annuus), Lamium purpureum, Kyllinga gracillima, Lythrum salicaria (Ammannia multiflora), Artemisia canadensis (Erigeron canadensis), Pondweed (Potamogeton distinctus A. Benn), Water hyacinth (Amaranthus tuberculatus), field pansy (Viola arvensis), Japanese thistle (Cirsium purpuratum), ragweed (Ambrosia artemisiifolia), Japanese ragweed (Schoenoplectus tabernaemontani), Japanese ragweed (Veronicahederaefolia, blackgrass (Alopecurus myosuroides), Florida beggarweed (Desmodium tortuosum), plantain (Plantago lanceolata), kochia (Kochia scoparia), burdock (Lolium rigidum), loose-leaved ryegrass (Ammannia coccinea), loose-leaved ryegrass (Lolium perenne), bulrush (Scirpus juncoides Roxburgh), henbit (Lamium amplexicaule), ash grass (Najas graminea), red amaranthus (Amaranthus hybridus), pine needles (Eleocharis acicularis L.), portulaca grandiflora, morning glory (Ipomoea lacunosa), round morning glory (Ipomoea purpurea, common morning glory (Ipomoea hederacea var integriuscula), common dayflower (Commelina bengharensis), black-eared water laurel (Monochoria korsakowii), common serotinus (Cyperus serotinus Rottboel), common chickweed (Elatine triandra Schk), large crabgrass (Digitaria ciliaris), large crabgrass (Digitaria sanguinalis), sorghum (Sorghum bicolor), cleaver (Galium aparine), mugwort (Artemisia princeps), wild pansy (Viola tricolor), wild radish (Raphanus raphanistrum), forget-me-not (Myosotis arvensis), and arrowhead (Alisma canaliculatum). The compound of the present invention represented by the general formula (I) or a salt thereof inhibits the growth of these weeds.

[0188] The compound represented by the general formula (I) of the present invention or its salts are generally formulated into a convenient form for use according to the conventional method for pesticide formulation. That is, the compound represented by the general formula (I) of the present invention or its salts may be formulated into a suitable inert carrier, or if necessary, together with an adjuvant, in an appropriate ratio, and then dissolved, separated, suspended, mixed, impregnated, adsorbed or attached to the carrier, and then formulated into a suitable dosage form, such as a suspension, emulsifiable concentrate, liquid, wettable powder, water dispersible granule, granule, dust, tablet, pack, etc.

[0189] The composition (agricultural and horticultural herbicide) of the present invention may contain, in addition to the active ingredient, additives commonly used in pesticide formulations or agricultural and horticultural herbicides, as needed. Examples of such additives include carriers such as solid carriers and liquid carriers, surfactants, dispersants, wetting agents, binders, tackifiers, thickeners, colorants, spreading agents, adhesives, antifreeze agents, anticaking agents, disintegrants, and antidecomposition agents. Other additives, such as preservatives and plant fragments, may also be used as needed. These additives may be used alone or in combination of two or more.

[0190] Examples of solid carriers include natural minerals such as quartz, clay, kaolinite, pyrophyllite, sericite, talc, bentonite, acid clay, attapulgite, zeolite, and diatomaceous earth, inorganic salts such as calcium carbonate, ammonium sulfate, sodium sulfate, and potassium chloride, organic solid carriers such as synthetic silicic acid, synthetic silicates, starch, cellulose, and plant powders (e.g., sawdust, coconut shells, corn cobs, and tobacco stalks), plastic carriers such as polyethylene, polypropylene, and polyvinylidene chloride, urea, inorganic hollow bodies, plastic hollow bodies, and fumed silica (fumed silica, white carbon). These may be used alone or in combination of two or more.

[0191] Examples of liquid carriers include monohydric alcohols such as methanol, ethanol, propanol, isopropanol, and butanol; polyhydric alcohols such as ethylene glycol, diethylene glycol, propylene glycol, hexylene glycol, polyethylene glycol, polypropylene glycol, and glycerin; polyhydric alcohol compounds such as propylene glycol ether; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, and cyclohexanone; ethers such as ethyl ether, dioxane, ethylene glycol monoethyl ether, dipropyl ether, and tetrahydrofuran; normal paraffin, naphthene, isopropyl alcohol, and the like. Examples of suitable solvents include aliphatic hydrocarbons such as paraffin, kerosene, and mineral oil, aromatic hydrocarbons such as benzene, toluene, xylene, solvent naphtha, and alkylnaphthalene, halogenated hydrocarbons such as dichloromethane, chloroform, and carbon tetrachloride, esters such as ethyl acetate, diisopropyl phthalate, dibutyl phthalate, dioctyl phthalate, and dimethyl adipate, lactones such as γ-butyrolactone, amides such as N,N-dimethylformamide, N,N-diethylformamide, N,N-dimethylacetamide, and N-alkylpyrrolidinone, nitriles such as acetonitrile, sulfur compounds such as dimethyl sulfoxide, vegetable oils such as soybean oil, rapeseed oil, cottonseed oil, and castor oil, and water. These may be used alone or in combination of two or more.

[0192] Examples of surfactants used as dispersants, wetting agents, spreading agents and spreaders include sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters, sucrose fatty acid esters, polyoxyethylene fatty acid esters, polyoxyethylene resin acid esters, polyoxyethylene fatty acid diesters, polyoxyethylene alkyl ethers, polyoxyethylene alkylaryl ethers, polyoxyethylene alkylphenyl ethers, polyoxyethylene dialkylphenyl ethers, polyoxyethylene alkylphenyl ether formalin condensates, polyoxyethylene polyoxypropylene block copolymers, polystyrene polyoxyethylene block polymers, alkyl polyoxyethylene polypropylene block copolymer ethers, polyoxyethylene alkylamines, polyoxyethylene fatty acid amides, polyoxyethylene fatty acid bisphenyl ethers, polyalkylene benzyl phenyl ethers, polyoxyalkylene styryl phenyl ethers, acetylenic diols, polyoxyalkylene-added acetylenic diols, polyoxyethylene ether-type silicones, and ester-type silicones. nonionic surfactants such as fluorine-based surfactants, polyoxyethylene castor oil, and polyoxyethylene hydrogenated castor oil; anionic surfactants such as alkyl sulfates, polyoxyethylene alkyl ether sulfates, polyoxyethylene alkyl phenyl ether sulfates, polyoxyethylene styryl phenyl ether sulfates, alkyl benzene sulfonates, alkyl aryl sulfonates, lignin sulfonates, alkyl sulfosuccinates, naphthalene sulfonates, alkyl naphthalene sulfonates, salts of formalin condensates of naphthalene sulfonic acid, salts of formalin condensates of alkyl naphthalene sulfonic acid, fatty acid salts, polycarboxylates, polyacrylates, N-methyl-fatty acid sarcosinates, resinates, polyoxyethylene alkyl ether phosphates, and polyoxyethylene alkyl phenyl ether phosphates; cationic surfactants such as alkyl amine salts such as laurylamine hydrochloride, stearylamine hydrochloride, oleylamine hydrochloride, stearylamine acetate, stearylaminopropylamine acetate, alkyltrimethylammonium chloride, and alkyldimethylbenzalkonium chloride;Amphoteric surfactants such as amino acid type or betaine type surfactants may be used alone or in combination of two or more types.

[0193] Examples of binders and tackifiers include carboxymethyl cellulose and its salts, dextrin, water-soluble starch, xanthan gum, guar gum, sucrose, polyvinylpyrrolidone, gum arabic, polyvinyl alcohol, polyvinyl acetate, sodium polyacrylate, polyethylene glycol having an average molecular weight of 6,000 to 20,000, polyethylene oxide having an average molecular weight of 100,000 to 5,000,000, phospholipids (for example, cephalin, lecithin, etc.), cellulose powder, dextrin, modified starch, polyaminocarboxylic acid chelate compounds, crosslinked polyvinylpyrrolidone, copolymers of maleic acid and styrenes, (meth)acrylic acid copolymers, half esters of polymers composed of polyhydric alcohols and dicarboxylic acid anhydrides, water-soluble salts of polystyrene sulfonic acid, paraffin, terpene, polyamide resins, polyacrylates, polyoxyethylene, wax, polyvinyl alkyl ethers, alkylphenol-formalin condensates, and synthetic resin emulsions.

[0194] Examples of thickeners include water-soluble polymers such as xanthan gum, guar gum, diutan gum, carboxymethyl cellulose, polyvinylpyrrolidone, carboxyvinyl polymers, acrylic polymers, starch compounds, and polysaccharides, and inorganic fine powders such as high-purity bentonite and fumed silica (white carbon).

[0195] Examples of colorants include inorganic pigments such as iron oxide, titanium oxide and Prussian blue, and organic dyes such as alizarin dyes, azo dyes and metal phthalocyanine dyes.

[0196] Examples of antifreezing agents include polyhydric alcohols such as ethylene glycol, diethylene glycol, propylene glycol, and glycerin.

[0197] Examples of adjuvants for preventing caking or promoting disintegration include polysaccharides such as starch, alginic acid, mannose, and galactose, polyvinylpyrrolidone, fumed silica (white carbon), ester gum, petroleum resin, sodium tripolyphosphate, sodium hexametaphosphate, metal stearates, cellulose powder, dextrin, methacrylic acid ester copolymers, polyvinylpyrrolidone, polyaminocarboxylic acid chelate compounds, sulfonated styrene-isobutylene-maleic anhydride copolymers, and starch-polyacrylonitrile graft copolymers.

[0198] Examples of anti-decomposition agents include desiccants such as zeolite, quicklime, and magnesium oxide; antioxidants such as phenol compounds, amine compounds, sulfur compounds, and phosphoric acid compounds; and ultraviolet absorbers such as salicylic acid compounds and benzophenone compounds.

[0199] Examples of preservatives include potassium sorbate, 1,2-benzothiazolin-3-one, etc. Furthermore, other adjuvants such as functional spreading agents, activity enhancers such as metabolic decomposition inhibitors such as piperonyl butoxide, antifreezing agents such as propylene glycol, antioxidants such as BHT, and ultraviolet absorbers may also be used as needed.

[0200] The blending ratio of the active ingredient compound can be adjusted as necessary and may be appropriately selected from the range of 0.01 to 90 parts by weight per 100 parts by weight of the agricultural and horticultural herbicide of the present invention. For example, when the agricultural and horticultural herbicide is formulated as a dust, granule, emulsifiable concentrate or wettable powder, the blending ratio is suitably 0.01 to 50% by weight based on the total weight of the agricultural and horticultural herbicide.

[0201] The amount of the compound represented by general formula (I) of the present invention or a salt thereof to be used will vary depending on various factors, such as the purpose, target weeds, the growth state of the crop, the tendency of weeds to appear, weather, environmental conditions, formulation, application method, application location, application time, etc., but may be appropriately selected depending on the purpose from the range of 0.001 g to 10 kg, preferably 0.01 g to 1 kg, of the active ingredient compound per 10 ares.

[0202] The agricultural and horticultural herbicides containing the compound represented by general formula (I) of the present invention or a salt thereof as an active ingredient can be directly sprayed onto the foliage of weeds in an amount effective for weed control, either as is or after being appropriately diluted or suspended in water or the like, to control various weeds. In addition, the agricultural and horticultural herbicides can also be used by treating the soil or cultivation carriers, for example, by immersing seeds in the herbicide, seed dressing, seed treatment of useful plants such as calper treatment, incorporation into the entire soil layer, row application, incorporation into bed soil, treatment with cell seedlings, treatment in planting holes, treatment at the base of plants, top dressing, treatment in rice boxes, application on the water surface, etc.

[0203] Methods for treating seeds of useful plants include, for example, a method in which seeds are soaked in a liquid or solid formulation, diluted or undiluted, to allow the agent to penetrate the seeds, a method in which a solid or liquid formulation is mixed with seeds and coated onto the seed surface, a method in which the formulation is mixed with an adhesive carrier such as a resin or polymer and then coated onto the seeds, a method in which the formulation is sprayed around the seeds at the same time as planting, etc. The "seeds" to be treated in this way refer to plant bodies in the early stages of cultivation used for propagating useful plants, and include, in addition to seeds, bulbs, tubers, seed potatoes, sprouts, bulbils, bulbs, or plant bodies for vegetative propagation for cutting cultivation.

[0204] When carrying out the method of use of the present invention, the term "soil" or "cultivation carrier" for plants refers to a support for cultivating crops, particularly a support for growing roots. The material is not particularly limited, and any material capable of growing useful plants may be used, such as soil, a seedling mat, or water. Specific examples of the material include sand, pumice, vermiculite, diatomaceous earth, agar, a gel-like substance, a polymeric substance, rock wool, glass wool, wood chips, and bark.

[0205] For application to rice seedling boxes, the formulation may vary depending on the application time, such as application at the time of sowing, application during the greening period, or application at the time of transplanting, but may be in the form of a dust, water dispersible granule, granule, or the like. Application can also be by mixing with the culture soil, and the culture soil can be mixed with a dust, water dispersible granule, or granule, for example, by mixing with the bed soil, mixing with the covering soil, or mixing with the entire culture soil. Application can also be simply by layering the culture soil and various formulations alternately.

[0206] Application to paddy fields typically involves spraying solid formulations such as jumbo, pack, granule, and water dispersible granules, or liquid formulations such as flowable and emulsifiable concentrates, onto flooded paddy fields. Additionally, appropriate formulations can be sprayed or injected directly into the soil at the time of rice planting, or mixed with fertilizer. Furthermore, labor-saving application can be achieved by using emulsions, flowables, and other chemical solutions at the source of water flow into paddy fields, such as water inlets and irrigation systems, along with the water supply. When spraying equipment is used, any commonly used equipment can be used, including pancrusher sprayers, manned helicopters, radio-controlled helicopters, radio-controlled boats, drones, one-shot sprayers, powered (manual or automatic) sprayers, carry-type power sprayers, backpack-type power sprayers, and manual sprayers.

[0207] The compound represented by general formula (I) of the present invention or a salt thereof can be used in combination with other herbicides, plant growth regulators, phytotoxicity reducers (safeners), soil conditioners, fertilizers, etc., in order to extend the range of weeds to be controlled or the optimum control period, or for the purpose of reducing the dosage, and can also be used in combination with agricultural and horticultural insecticides, miticides, nematicides, fungicides, biological pesticides, etc., depending on the application scene. Representative compounds are exemplified below, but the present invention is not limited to these.

[0208] Other agricultural and horticultural insecticides, acaricides, and nematicides used for such purposes include, for example, 3,5-xylyl methylcarbamate (XMC), fenobucarb (BPMC), Bt toxin-based insecticides, CPCBS (chlorfenson), DCIP (dichlorodiisopropyl ether), DD (1,3-dichloropropene), DDT, NAC, O-4-dimethylsulfamoylphenyl O,O-diethyl phosphorothioate (DSP), and O-ethyl O-4-nitrophenyl Phenylphosphonothioate (EPN), tripropylisocyanurate (TPIC), acrinathrin, azadirachtin, acinonapyr, azinphos-methyl, acequinocyl, acetamiprid, acetoprole, acephate, abamectin, afidopyropen, avermectin-B, amidoflumet idoflumet), amitraz, alanycarb, aldicarb, aldoxycarb, aldrin, alpha-endosulfan, alpha-cypermethrin, albendazole, allethrin, isazofos, isamidofos, isamidofos, isoxathion, isocycloseram, isofenphos, isoflenam, isoflualanum, isoprocarb (MIPC), epsilon-metofluthrin,Epsilon-momfluorothrin, ivermectin, imicyafos, imidacloprid, imiprothrin, indazapyroxamet, indoxacarb, vadescana, esfenvalerate, ethiofencarb ncarb), ethion, ethiprole, etoxazole, etofenprox, ethoprophos, etrimfos, emamectin, emamectin benzoate, endosulfan, empenthrin, oxazosulfyl, oxamyl, oxydemeton-methyl, oxydeprofos (ESP), oxibendazole, oxfendazole, potassium oleate, sodium oleate oleate, cadusafos, kappa-bifenthrin, cartap, carbaryl, carbosulfan, carbofuran, gamma-cyhalothrin, xylylcarb, quinalphos, kinoprene, chinomethionate, cloethocarb, clothianidin, clofentezine, chromafenozide, chlorantraniliprole,Chlorethoxyfos, chlordimeform, chlordane, chlorpyrifos, chlorpyrifos-methyl, chlorphenapyr, chlorfenson, chlorfenvinphos, chlorfluazuron, chlorobenzilate, chlorobenzoate, chloroprallethrin, dicofol, salithion, cyhalodiamide, cyanophos CYAP), diafenthiuron, diamidaphos, cyantraniliprole, theta-cypermethrin, dienochlor, cyetpyrafen, cyenopyrafen, dioxabenzofos, diofenolan, sigma-cypermethrin, cyclaniliprole, diclofenthion (ECP), cycloprothrin, dichlorvos (dichlorvos) DDVP), dichloromezotiaz, disulfoton, dinotefuran, cyhalodiamide, cyhalothrin, cyphenothrin, cyfluthrin, diflubenzuron, cyflumetofen, diflovidadin, cyproflanilide,Cyhexatin, cypermethrin, cybenzoxasulfyl, dimethylvinphos, dimethoate, dimpropyridaz, dimefluthrin, silafluofen, cyromazine, spidoxamat, spinetoram, spinosad, spirodiclofen, spirotetramat, spiropidione, spirobudifen, spinosad Spiromesifen, sulfiflumin, sulfluramid, sulprofos, sulfoxaflor, zeta-cypermethrin, diazinon, tau-fluvalinate, dazomet, thiacloprid ), thiapyrachlor, thiamethoxam, tioxazafen, thiodicarb, thiocyclam, thiosultap, thiosultap sodium, thionazin, thiometon, thiolanthraniliprole, DEET, dieldrin, tetrachlorantraniliprole, cyclopyrazoflor, tetrachlorvinphos, tetradifon, tetraniliprole, tetramethylfluthrin,Tetramethrin, tebupirimfos, tebufenozide, tebufenpyrad, tefluthrin, teflubenzuron, demeton-S-methyl, temephos, deltamethrin, terbufos, doramectin, tralopyril, tralomethrin, transfluthrin, triazamate, triazuron, trichlamide, trichlorphon DEP), trifluenfuronate, triflumezopyrium, triflumuron, tolfenpyrad, naled BRP), nicofluprole, nithiazine, nitenpyram, novaluron, noviflumuron, hydroprene, vaniliprole, vamidothion, parathion, parathion-methyl, halfenprox, halofenozide, pioxaniliprole, bistrifluron, bisultap, bisulflufen, hydramethylnon, hydroxypropyl starch starch), binapacryl, piperflanilide, pyflubumide, bifenazate,Bifemetstrobin, bifenthrin, pymetrozine, pyraclofos, pyrafluprole, pyridaphenthion, pyridaben, pyridalyl, pyrifluquinazon, pyriprole, pyriproxyfen, pirimicarb, pyrimidifen, pyriminostrobin, pirimiphos-methyl, pyrethrins, fipronil, fenazaquin, fenamiphos, phenisobromorate, fenitrothion. MEP), fenoxycarb, fenothiocarb, fenothrin, fenobucarb, fensulfothion, fenthion (MPP), phenthoate (PAP), fenvalerate, fenpyroximate, fenpropathrin, fenbendazole, fenmezoditiaz, fosthiazate, formetanate, butathiofos , buprofezin, furathiocarb, prallethrin, fluacrypyrim, furazaindolizine, fluazinam, fluazuron, fluensulfone, fluxametamide,Fluchlordiniliprole, flucycloxuron, flucythrinate, fluvalinate, flupyradifurone, flufiprole, flupyradifurone, flupyrazofos, flupyrimin , flufenerim, flufenoxystrobin, flufenoxuron, flufenzine, flufenprox, flupyroxystrobin, fluproxyfen, flubrocythrinate, fluhexafon, flubendiamide, flupentiofenox, flumetnicam, flumethrin, flurimfen, prothiofos, protrifenbute, flonicamid, propaphos, propargite BPPS), profenofos, broflanilide, profluthrin, propoxur (PHC), flometoquin, alpha-bromadiolone, bromopropylate, beta-cyfluthrin, hexaflumuron, hexythiazox, heptafluthrin, heptenophos, permethrin, benclothiaz, bendiocarb,benzpyrimoxan, bensultap, benzoximate, bentiofluormin, benfuracarb, phoxim, phosalone, fosthiazate, fosthietan, phosphamidon, phosphocarb, phosmet (PMP), polynactins, formetanate, formothion, phorate, machine oil oil), malathion, milbemycin, milbemycin A, milbemectin, mecarbam, mesulfenphos, methomyl, metaldehyde, metaflumizone, methamidophos, metam-ammonium, metam-sodium, methiocarb, methidathion DMTP), methylisothiocyanate, methylneodecanamide, methylparathion, metoxadiazone, methoxychlor, methoxyfenozide, metofluthrin, methoprene, metolcarb, meperfluthrin, mevinphos, monocrotophos, monosultap, momfluorothrin, lambda-cyhalothrin,Examples of such antihistamines include ryanodine, lufenuron, lescalure, resmethrin, lepimectin, rotenone, levamisol hydrochloride, fenbutatin oxide, morantel tartarate, methyl bromide, tricyclohexyltin hydroxide, calcium cyanamide, calcium polysulfide, sulfur, and nicotine sulfate.

[0209] Agricultural and horticultural fungicides used for similar purposes include, for example, aureofungin, azaconazole, azithiram, acipetax, acibenzolar, acibenzolar-S-methyl, azoxystrobin, anilazine, amisulbrom, ampropylfos, ametoctradin, and allyl alcohol. alcohol), aldimorph, amobam, isotianil, isovaledione, isopyrazam, isofetamide, isofetamid, isoflucipram, isoprothiolane, ipconazole, ipfentrifluconazole, ipflufenoquin, iprodione, iprovalicarb, iprobenfos, imazalil, iminoctadine, metam (metam), iminoctadine albesilate, iminoctadine acetate, iminoctadine triacetate, imibenconazole, inpyrfluxam, uniconazole, uniconazole-P, echlomezole, edifenphos, etaconazole, etaboxam, ethirimol, etem, ethoxyquin, etridiazole, enestroburin,Enoxastrobin, epoxiconazole, oxadixyl, oxathiapiprolin, oxycarboxin, copper-8-quinolinolate, oxytetracycline, copper-oxinate, oxpoconazole, oxpoconazole-fumarate, oxolinic acid acid), octhilinone, ofurace, orysastrobin, carbam (metam-sodium), kasugamycin, galquin, carbamorph, carpropamid, carbendazim, carboxin, carvone, quinazamid, quinacetol, quinoxyfen, quinofumelin, chinomethionate , quinomethionate), captafol (captafol), captan (captan), chiralaxyl (kiralaxyl), quinconazole (quinconazole), quintozene (quintozene), guazatine (guazatine), cufraneb (cufraneb), cuprobam (cuprobam), coumoxystrobin (coumoxystrobin), glyodin (glyodin), griseofulvin (griseofulvin), climbazole (climbazole), cresol (cresol), kresoxim-methyl (kresoxim-methyl), chlozolinate (chlozolinate), clotrimazole (clotrimazole), chlobenthiazone (chlobenthiazone), chloraniformethan (chloraniformethan), chloranil (chloranil),Chlorquinox, chloropicrin, chlorphenazole, chloroinconazide, chlorodinitronaphthalene, chlorothalonil, chloroneb, salicylanilide, zalilamid, cyazofamid, diethyl pyropacarbonate pyrocarbonate, diethofencarb, cyclafuramid, cyclocymet, dichlozoline, diclobutrazol, cyclobutrifluram, dichlofluanid, cycloheximide, dichlobentiazox, diclomezine, dicloran, dichlorophen, dichlorone, disulfiram, ditalimfos, dithianon, dithianon Niconazole (diniconazole), diniconazole-M (diniconazole-M), zineb (zineb), dinocap (dinocap), dinocton (dinosulfon), dinoterbone (dinoterbon), dinobuton (dinobuton), dinopenton (dinopenton), dipymetitrone (dipyrithione), diphenylamine (diphenylamine), difenoconazole (difenoconazole), cyflufenamid (cyflufenamid), diflumetorim (diflumetorim), cyproconazole (cyproconazole), cyprodinil (cyprodinil), cyprofuram (cyprofuram),Cypendazole, simeconazole, dimethirimol, dimethomorph, cymoxanil, dimoxystrobin, ziram, silthiofam, streptomycin, spiroxamine, sultropen, sedaxane, zoxamide, dazomet, thiadiazin, tiadinil, thiadifluor, thiadiphenylmethane abendazole, thioximid, thiochlorfenphim, thiophanate, thiophanate-methyl, thifluzamide, thicyofen, thioquinox, thiram, decafentin, tecnazene, tecloftalam, tecoram, tetraconazole, debacarb, dehydroacetic acid acid), tebuconazole, tebufloquin, dodicin, dodine, dodecylbenzenesulfonic acid bisethylenediamine copper complex salt (II) (DBEDC), dodemorph, drazoxolon, triadimenol, triadimefon, triazbutil, triazoxide, triamiphos, triarimol, trichlamide, triclopyricarb, tricyclazole,Triticonazole, tridemorph, tributyltin oxide, triflumizole, trifloxystrobin, triforine, tolylfluanid, tolclofos-methyl, tolprocarb, natamycin, nabam, nitrostyrene, nitrothal-isopropyl, nuarimol, copper nonylphenol sulfonate, halacrinate, validamycin, valifenalate, harpin protein protein), picarbutrazox, bixafen, picoxystrobin, picobenzamide, pydiflumetofen, bithionol, bitertanol, hydroxyisoxazole, hydroxyisoxazole-potassium, binapacryl, biphenyl , piperalin, hymexazol, pyraoxystrobin, pyracarbolid, pyraclostrobin, pyraziflumid, pyrazophos, pyrapropoin, pyrametostrobin, pyriophenone, pyridinitril, pyridiflumetofen,Pyrisoxazole, pyridaclomethyl, pyrifenox, pyribencarb, pyriminostrobin, pyrimethanil, pyroxychlor, pyroxyfur, pyroquilon, vinclozolin, ferbam, famoxadone , fenapanil, fenamidone, fenaminosulf, phenaminestrobin, fenarimol, fenitropan, feneptamidoquin, fenoxanil, fenopyramide, ferimzone, ferbam, fentin, fenpiclonil fenpiclonil, fenpicoxamid, fenpyrazamine, fenbuconazole, fenfuram, fenpropidin, fenpropimorph, fenhexamid, phthalide, buthiobate, butylamine, bupirimate, fuberidazo fuberidazole, blasticidin S, furametpyr, furalaxyl, fluacrypyrim, fluazinam, fluindapyr, fluoxastrobin, fluoxapiprolin, fluoxytioconazole, fluotrimazole,Fluopicolide, fluopimomide, fluopyram, fluoroimide, furcarbanil, fluxapyroxad, fluquinometoate, fluquinconazole, furconazole, fluconazole-cis, fludioxonil il), flusilazole, flusulfamide, flutianil, flutolanil, flutriafol, flufenoxadiazam, flufenoxystrobin, furfural, flubeneteram, flumecyclox, flumethylsulfolim ulform, flumetover, flumorph, proquinazid, prochloraz, procymidone, prothiocarb, prothioconazole, pronitridine, propamocarb, propiconazole, propineb, furophanate anate), probenazole, bromuconazole, florylpicoxamid, hexachlorobutadiene, hexaconazole, hexylthiofos, bethoxazin, benalaxyl, benalaxyl-M, benodanil, benomyl,Pefurazoate, benquinox, penconazole, benzamorph, pencycuron, benzohydroxamic acid acid, benzovindiflupyr, bentaluron, benthiazole, benthiavalicarb, benthiavalicarb-isopropyl, penthiopyrad, penflufen, boscalid, phosdiphen, fosetyl, fosetyl-aluminum, polyoxins, polyoxolin, polycarbamate, folpet, formaldehyde, machine oil oil), maneb, mancozeb, mandipropamid, mandestrobin, myclozolin, myclobutanil, mildiomycin, milneb, mecarbinzid, methasulfocarb, metazoxolone, metam, metam-sodium, metalaxyl, metalaxyl-M, metarylpicoxamid, metiram, methyl isothiocyanate isothiocyanate), methyldinocap, methyltetraprole, metconazole, metsulfovax, metofuroxam,Inorganic disinfectants such as metominostrobin, metrafenone, mepanipyrim, mefenoxam, mefentrifluconazole, meptyldinocap, mepronil, mebenil, methyl iodide, rabenzazole, methyl bromide, benzalkonium chloride, basic copper chloride, basic copper sulfate, metallic silver, sodium hypochlorite, cupric hydroxide, wettable sulfur, calcium polysulfide, potassium hydrogen carbonate, etc. Examples of suitable organic solvents include copper compounds such as copper carbonate, sodium hydrogen carbonate, inorganic sulfur, copper sulfate anhydride, nickel dimethyldithiocarbamate, and 8-hydroxyquinoline copper (oxine copper), zinc sulfate, and copper sulfate pentahydrate.

[0210] Other herbicides used for this purpose include, for example, 1-naphthylacetamide, 2,4-PA, 2,3,6-TBA, 2,4,5-T, 2,4,5-TB, 2,4-D, 2,4-DB, 2,4-DEB, 2,4-DEP, 3,4-DA, 3,4-DB, 3,4-DP, 4-CPA, 4-CPB, 4-CPP, MCP, MCPA, MCPA thioethyl, MCPB, ioxynil, icafolin, aclonifen, azafenidin, Acifluorfen, Aziprotryne, Azimsulfuron, Asulam, Acetochlor, Atrazine, Atraton, Anisuron, Anilofos, Aviglycine, Abscisic Acid acid, amicarbazone, amidosulfuron, amitrole, aminocyclopyrachlor, aminopyralid, amivudine, amiprophos-methyl, ametridione, ametryn, alachlor, allidochlor, alloxydim, and alora c), iofensulfuron, isouron, isocarbamide, isoxachlortole, isoxapyrifop, isoxaflutole, isoxaben, isocil, isonoruron, isoproturon, isopropalin, isopolinate, isomethiozin,Inabenfide, ipazine, iptriazopyrid, ipfencarbazone, iprimidam, imazaquin, imazapic, imazapyr, imazamethapyr, imazamethabenz, imazamethabenz-methyl, imazamox, imazethapyr, imazosulfuron, indaziflam, indanofan, indolauxipyr, indolauxipyr-cyanomethyl, indolebutyric acid acid), uniconazole-P, eglinazine, esprocarb, ethametsulfuron, ethametsulfuron-methyl, ethalfluralin, ethiolate, ethychlozate-ethyl ethyl), etidimuron, ethinofen, ethephon, ethoxysulfuron, ethoxyfen, etonipromide, etofumesate, etobenzanid, epirifenacil, epronaz, erbon, endothal, oxadiazon, oxadiargyl, oxaziclomefone, oxasulfuron, oxapyrazon, oxyfluorfen,Oryzalin, orthosulfamuron, orbencarb, cafenstrole, cambendichlor, carbasulam, carfentrazone, carfentrazone-ethyl, karbutilate, carbetamide, carboxazole azole), quizalofop, quizalofop-P, quizalofop-ethyl, xylachlor, quinoclamine, quinonamid, quinclorac, quinmerac, cumyluron, clacyfos, cliodinate, glyphosate, Glufosinate, glufosinate-P, credazine, clethodim, cloxyfonac, clodinafop, clodinafop-propargyl, chlortoluron, clopyralid, cloproxydim, cloprop, clobromuron hlorbromuron), clofop, clomazone, chlomethoxynil, chlomethoxyfen, clomeprop, chlorazifop, chlorazine, chlorasulam, chloranocryl, chloramben, chloransulam-methyl,Chloridazon, chlorimuron, chlorimuron-ethyl, chlorsulfuron, chlorthal, chlorthiamid, chlornitrofen, chlorfenac, chlorfenprop, chlorbufam, chlorflurazol e), chlorflurenol, chlorprocarb, chlorpropham, chlormequat, chloreturon, chloroxynil, chloroxuron, chloropon, saflufenacil, cyanazine, cyanatrin, di-allate , diuron, diethamquat, dioxopyritrione, dicamba, cycluron, cycloate, cycloxydim, diclosulam, cyclosulfamuron, cyclopyranil, cyclopyrimorate, dichlorprop, di Dichlorprop-P, dichlobenil, diclofop, diclofop-methyl, dichromate, dichloralurea, diquat, cisanilide, disul, siduron, dithiopyr, dinitramine, cinidon-ethyl,Dinosam, cinosulfuron, dinoseb, dinoterb, dinofenate, dinoprop, cyhalofop-butyl, cypyrafluone, diphenamid, difenoxuron, difenopenten, difenzoquat, sibutrin ryne), cyprazine, cyprazole, diflufenican, diflufenzopyr, dipropetryn, cypromid, cyperquat, gibberellin, simazine, dimexano, dimesulfazet, dimethachlor, dimedazone dazon, dimethametryn, dimethenamid, simetryn, simeton, dimepiperate, dimefuron, cinflubrolin, cinmethylin, swep, sulglycapin, sulcotrione, sulfate, sulfentrazone fentrazone, sulfosulfuron, sulfometuron, sulfometuron-methyl, secbumeton, sethoxydim, sebuthylazine, terbacil, daimuron, dazomet, dalapon, thiazafluron, thiazopyr,Thiafenacil, thiencarbazone, thiencarbazone-methyl, thiocarbazil, thioclorim, thiobencarb, thidiazimin, thidiazuron, thifensulfuron, thifensulfuron-methyl, desmede Desmedipham, desmetryn, tetflupyrolimet, tetrafluron, thenylchlor, tebutam, tebuthiuron, terbumeton, tepraloxydim, tefuryltrione, tembotrione, delachlor, ter Terbacil, terbucarb, terbuchlor, terbuthylazine, terbutryn, topramezone, tralkoxydim, triaziflam, triasulfuron, triafamone, tri-allate, trietazine, tricamba amba), triclopyr, tridiphane, tritac, tritosulfuron, tripyrasulfone, trifludimoxazin, triflusulfuron, triflusulfuron-methyl, trifluralin, trifloxysulfuron,Tripropindan, tribenuron-methyl, tribenuron, triphop, trifopsime, trimeturon, tolpyralate, naptalam, naproanilide, naproxen, nicosulfuron, nitralin, nitrofen (nitrofen), nitrofluorfen, nipiraclofen, neburon, norflurazon, noruron, barban, paclobutrazol, paraquat, parafluron, haloxydine, halauxifen, haloxyfop, haloxyfop -P (haloxyfop-P), haloxyfop-methyl, halosafen, halosulfuron, halosulfuron-methyl, bixlozone, picloram, picolinafen, bicyclopyrone, bispyribac, bispyribac-sodium, Pidanone, pinoxaden, bipyrazone, bifenox, piperophos, hymexazol, pyraquinate, pyraclonil, pyrasulfotole, pyrazoxyfen, pyrazosulfuron, pyrazosulfuron-ethyl,Pyrazolate, bilanafos, pyraflufen-ethyl, pyriclor, pyridafol, pyrithiobac, pyrithiobac-sodium, pyridate, pyriftalid, pyributicarb, pyriflubenzoxim, pyribenzoxin Pyribenzoxim, pyrimisulfan, pyrimisulfuron, pyriminobac-methyl, feproxydim, flusulfinam, broclozone, pyroxasulfone, pyroxsulam, fenasulam, phenisopham, fenuron fenuron, fenoxasulfone, fenoxaprop, fenoxaprop-P, fenoxaprop-ethyl, phenothiol, fenoprop, fenobenzuron, fenquinotrione, fentiaprop, fenteracol, fentrazamide ( fentrazamide, fenpyrazone, phenmedipham, phenmedipham-ethyl, butachlor, butafenacil, butamifos, buthiuron, buthidazole, butyrate, buturon, butenachlor, butroxydim,Butralin, flazasulfuron, flamprop, furyloxyfen, prinachlor, primisulfuron-methyl, fluazifop, fluazifop-P, fluazifop-butyl, fluazolate, fluchloraminopyr r), fluchloraminopyr-tefuryl, fluroxypyr, fluothiuron, fluometuron, fluoroglycofen, flurochloridone, fluorodifen, fluoronitrofen, fluoromidine, flucarbazone ), flucarbazone sodium, fluchloralin, flucetosulfuron, fluthiacet, fluthiacet-methyl, flupyrsulfuron, flufenacet, flufenoximacil, flufenican, flufenpyr, flu Propasil (flupropacil), flupropanate (flupropanate), flupoxam (flupoxam), flumioxazin (flumioxazin), flumiclorac (flumiclorac), flumiclorac-pentyl (flumiclorac-pentyl), flumipropyn (flumipropyn), flumezin (flumezin), fluometuron (fluometuron), flumetsulam (flumetsulam), fluridone (fluridone), flurtamone (flurtamone),Fluroxypyr, pretilachlor, proxan, proglinazine, procyazine, prodiamine, prosulfalin, prosulfuron, prosulfocarb, propaquizafop, propachlor, propazine, propani propanil, propyzamide, propisochlor, prohydrojasmon, propyrisulfuron, propham, profluazol, profluralin, prohexadione-calcium, propoxycarbazone, propoxycarbazone sodium opoxycarbazone-sodium, profoxydim, bromacil, brompyrazone, prometryn, prometon, bromoxynil, bromofenoxim, bromobutide, bromobonil, florasulam, florpyrauxifen, hexafluoropropane, Hexachloroacetone, hexazinone, pethoxamid, benazolin, penoxsulam, pebulate, beflubutamid, beflubutamid-M, vernolate, perfluidone, bencarbazone, benquitrione,Benzadox, benzipram, benzylaminopurine, benzthiazuron, benzfendizone, bensulide, bensulfuron-methyl, benzoylprop, benzobicyclon, benzofenap, benzofluor , bentazone, pentanochlor, benthiocarb, pendimethalin, pentoxazone, benfluralin, benfuresate, fosamine, fomesafen, foramsulfuron, forchlorfenuron, maleic hydrazide hydrazide), mecoprop, mecoprop-P, medinoterb, mesosulfuron, mesosulfuron-methyl, mesotrione, mesoprazine, mesoprothrin, metazachlor, methazole, metazosulfuron ), methabenzthiazuron, metamitron, metamifop, metam, methalpropalin, methiuron, methiozolin, methiobencarb, methyldymron, metoxuron, metosulam, metsulfuron,Metsulfuron-methyl, metflurazon, metobromuron, metobenzuron, methometon, metolachlor, metribuzin, mepiquat chloride, mefenacet, mefluidide, metproxybicyclone, monalide, monisouron, monunuron, monochloroacetic acid Examples of suitable herbicides include iodosulfuron, monolinuron, molinate, morphamquat, iodosulfuron, iodosulfuron-methyl-sodium, iodobonil, iodomethane, lactofen, lancotrione, linuron, rimisoxafen, rimsulfuron, lenacil, rhodetanil, calcium peroxide, and methyl bromide. They can also be used in combination with biological pesticides used as herbicides against Xanthomonas campestris, etc.

[0211] Furthermore, as a safener, for example, 1,8-naphthalic anhydride, isoxadifen-ethyl, furilazole, cyprosulfamide, cyometrinil, dichlormid, dimepiperate, thiencarbazone-methyl, fenchlorazole-ethyl, fenclorim, fluxofenim, flurazole, benoxacor, metcamifen, mefenpyr-diethyl, and the like can also be used in combination.

[0212] Examples of biological pesticides include Agrobacterium radiobacter (e.g., "Galltrol-A (registered trademark)" manufactured by AgBioChem, CA using strain K84, and "Nogall (registered trademark)" manufactured by Becker Underwood, US using strain K1026), Agrobacterium radiobacter (e.g., "Bacteroise (registered trademark)" manufactured by Nippon Nohyaku Co., Ltd. using strain 84), Ampelomyces quisqualis (e.g., "AQ10 (registered trademark)" manufactured by IntrachemBio Italia & Co. KG using strain AQ10), Aspergillus flavus (e.g., "Afla-Guard (registered trademark)" manufactured by Syngenta and "Arizona Cotton Research and Protection (Arizona Cotton Research and Protection)" using strain AF36), and AF36® from Council, US, Afla-Guard from Syngenta using NRRL 21882), Aureobasidium pullulans (e.g., Botector® from bio-ferm, GmbH, which is a mixture of blastospores of strain DSM 14940 and blastospores of strain DSM 14941),

[0213] Bacillus amyloliquefaciens (e.g., Impression Clear (registered trademark) manufactured by Idemitsu Agri Co., Ltd. using strain AT-332, and Avogreen (registered trademark) manufactured by University of Pretoria using strain B246), strain D747 (e.g., Bacstar (registered trademark) manufactured by Etec Crop Solutions, NZ, Shelter (registered trademark) manufactured by Dagutat Biolab, ZA using strain DB101, Artemis (registered trademark) manufactured by Dagutat Biolab, ZA using strain DB102, RhizoVital (registered trademark) manufactured by ABiTEP, DE using strain FZB42, Kodiak (registered trademark) manufactured by Bayer Crop Science AG, DE using strain GB03, and Becker (registered trademark) manufactured by Bayer Crop Science AG, DE using strain MBI600) are also known. Subtilex® from Underwood, US, Amplitude from Marrone Bio Innovations, Inc. using strain F727), Bacillus cepacia (e.g., Deny Stine® from Microbial Products), Bacillus cereus (e.g., Mepichlor® from Arysta, US using strain BP01), Bacillus firmus (e.g., BioNeem® from AgoGreen using strain I-1582),

[0214] Bacillus lacticola (e.g., from Micro Flo Company), Bacillus lactimorbus (e.g., from Micro Flo Company), Bacillus lactis (e.g., from Micro Flo Company), Bacillus laterosporus (e.g., from Agro-Organics, SA under the trademark Bio-Tode), Bacillus licheniformis (e.g., from Novozymes under the trademark EcoGuard Biofungicide using strain SB3086), Bacillus maroccanus (e.g., from Micro Flo Company), Bacillus megaterium (e.g., from Bio Fungicide using strain YFM3.25), Bacillus lacticola (e.g., from Micro Flo Company), Bacillus lactimorbus (e.g., from Micro Flo Company), Bacillus lactis ... Bioarc® from BioArc), Bacillus metiens (e.g., from Micro Flo Company), Bacillus mojavensis (e.g., from Probelte, Sa using strain SR11), Bacillus mycoides (e.g., BmJ® from Certis USA using isolate J.),

[0215] Bacillus nigrificans (e.g., manufactured by Micro Flo Company), Bacillus popilliae (e.g., "Cronox®" manufactured by Bio Crop, CO), Bacillus pumilus (e.g., "Integral F-33®" manufactured by Becker Underwood, US using strain BUF-33, "Yield Shield®" manufactured by Bayer Crop Science AG, DE using strain GB34, "Sonata®" manufactured by Bayer CropScience LP, US using strain QST2808), Bacillus simplex (e.g., "Momiphope Wettable Powder®" manufactured by Arista Life Sciences, Inc. using strain CGF2856), Bacillus sphaericus sphaericus) (e.g., VectoLex® from Valent BioSciences, US, using the serotype H5a5b strain 2362),

[0216] Bacillus subtilis (e.g., "Botokilla Wettable Powder (registered trademark)" manufactured by Idemitsu Agri Co., Ltd., "Taegro (registered trademark)" manufactured by Novozyme Biologicals, Inc. US using strain FZB24, "SERENADE (registered trademark)" manufactured by Bayer CropScience LP, US using strain QST713 / AQ713) MAX (registered trademark), Serenade-DPZ (registered trademark) using strain AQ30002, Ecoshot (registered trademark) manufactured by Kumiai Chemical Co., Ltd. using strain D747, Agrocare Wettable Powder (registered trademark) manufactured by Nisso Green Co., Ltd. using strain HAI-0404, Botopika Wettable Powder (registered trademark) manufactured by Idemitsu Kosan Co., Ltd. using strain MBI600, Batistar Wettable Powder (registered trademark) manufactured by Arista Life Sciences Co., Ltd. using strain Y1336, Companion Biological Fungicide Wettable Powder (registered trademark) manufactured by Growth Products Ltd. using strain GB03), Bacillus thuringiensis (e.g., VectoBac (registered trademark) manufactured by Valent BioSciences, US using strain AM65-52), Bacillus thuringiensis aizawai (Bacillus thuringiensis aizawai) (for example, "XenTari (registered trademark)" manufactured by "Bayer Crop Science AG, DE" using strain ABTS-1857, or "Valent BioSciences,"Florbac WG" manufactured by Certis USA using strain GC-91, "Agree WG Biological Insecticide" manufactured by Certis USA using strain GC-91, Bacillus thuringiensis subspecies. Aegypti (e.g., "Agerin"); Bacillus thuringiensis israelensis (e.g., "Aquabac" manufactured by Becker Microbial Products IL using strain BMP144);

[0217] Bacillus thuringienses kurstaki (e.g., strain BMP 123 manufactured by Becker Microbial Products, IL; strain HD-1 manufactured by Valent BioSciences, US; BMP 123 manufactured by Becker Microbial Products; strain BMP144 / Aquabac manufactured by Becker Microbial Products; strain ABTS-351 manufactured by Valent U.S.A. LLC; strain EG2348 manufactured by Certis USA; strain EG7841 manufactured by Certis USA; strain SA-12 ... Insecticide, Bioprotec PLUS from AEF Global using strain EVB-113-19), Bacillus thuringiensis galleriae (e.g., beetleGONE! from Phyllom BioProducts and boreGONE! from Phyllom BioProducts using strain SDS-502),

[0218] Bacillus thuringiensis var. Colmeri (e.g., TianBaoBTc® from Changzhou Jianghai Chemical Factory), Bacillus thuringienses tenebrionis (e.g., Novodor FC® from BioFa DE using strain NB176), Bacillus thuringiensis var. san diego (e.g., M-One® from Bacillus thuringiensis var. san diego), Beauveria bassiana (e.g., Naturalis® from Intrachem Bio Italia and Bove® from Novozymes using strain CG716), Bacillus thuringiensis var. san diego (e.g., Naturalis® from Intrachem Bio Italia and Bove® from Novozymes using strain CG716), Bacillus thuringiensis var. san diego (e.g., M-One® from Bacillus thuringiensis var. san diego), Bacillus thuringiensis var. san diego (e.g., Naturalis® from Intrachem Bio Italia and Bove® from Novozymes using strain CG716), Bacillus thuringiensis var. san diego (e.g., ... Max (registered trademark), Biolisa Madara (registered trademark) manufactured by Idemitsu Kosan Co., Ltd. using strain F-263, BotaniGard Wettable Powder (registered trademark) manufactured by ARYSTA using strain GHA, balEnce manufactured by Terragena, Inc. using strain HF23, BotaniGard ES manufactured by BioWorks Inc. using strain GHA, and BioCeres WP manufactured by BioSafe Systems using strain ANT-03.

[0219] Beauveria brongniartii (e.g., Beaupro® from Andermatt Biocontrol AG), Bradyrhizobium japonicum (e.g., Optimize® from Novozymes), Burkholderia spp. (e.g., MBI-206 TGAI® from Marrone Bio Innovations using strain A396), Candida oleophila (e.g., Aspire® from Ecogen Inc., US using strain I-82 and Nexy® from BioNext using strain O), Candida saitoana (e.g., Micro Flo Company, US (BASF BIOCURE® from AgriLife), Chaetomium cupreum (e.g., BIOKUPRUM™ from AgriLife), Chaetomium globosum (e.g., Rivadiom® from Rivale), Chromobacterium subtsugae (e.g., Grandevo® from Marrone Bio Innovations using strain PRAA4-1T),

[0220] Cladosporium cladosporioides (e.g., manufactured by Cladosporium cladosporioides), Clonostachys rosea f. catenulate (e.g., manufactured by Verdera, Finland in the form of PRESTOP® using strain J1446), Colletotrichum gloeosporioides (e.g., manufactured by Agriultural Research Initiatives in the form of Collego®), Coniothyrium minitans (e.g., manufactured by Encore Technologies, LLC in the form of Contans® using strain CON / M / 91-08), Cryptococcus albidus (e.g., manufactured by Anchor Bio Technologies, ZA), Delftia acidovorans (e.g., BioBoost® from Brett Young Seeds using strain RAY209), Dilophosphora alopecuri (e.g., Twist Fungus®), Drechsrela monoceras (e.g., Tasmart Herbicide® from Mitsui Chemicals Agro Inc. using strain MTB-951), Entomophthora virulenta (e.g., Vektor® from Ecomic), Fusarium oxysporum oxysporum (e.g., "Marcalite" manufactured by Eisai Seikaken Co., Ltd. using strain 101-2), Fusarium oxysporum (e.g., "Fusaclean (registered trademark)" manufactured by Natural Plant Protection using strain Fo47),

[0221] Gliocladium spp. (e.g., Prestop (registered trademark) manufactured by AgBio Inc. using strain J1446 and W.F. Stoneman Company LLC using strain 321U), Hirsutella thompsonii (e.g., Mycohit (registered trademark) manufactured by Agro Biotech Research Centre, IN), Lactobacillus acidophilus (e.g., Fruitsan (registered trademark) manufactured by Inagrosa Industrias Agrobiologicas, S.A.), Lactobacillus plantarum (e.g., Lactoguard Wettable Powder manufactured by Meiji Seika Pharma Co., Ltd. using strain BY), Lecanicillium lecanii lecanii) (e.g., "Mycotal (registered trademark)" manufactured by Koppert / Arysta using conidia of the strain KV01), Metarhizium anisopliae (e.g., "BIO 1020 (registered trademark)" manufactured by Bayer CropScience using the strain F52, "Pirate Granules (registered trademark)" manufactured by Arysta LifeSciences Inc. using the strain SMZ-2000, and "Bio-Blast" manufactured by LidoChem Inc. using the strain ESC1),

[0222] Metarhizium anisopliae var. acridum (e.g., "Green Muscle®" manufactured by Biological Control Products, and "Becker Underwood,US), Metschnikowia fructicola (e.g., Shemer® from Bayer CropScience), Microdochium dimerum (e.g., ANTIBOT® from Agrauxine, France), Microsphaeropsis ochracea (e.g., Microx® from Prophyta), Monacrosporium phymatopagum (e.g., Nemahiton® from Tomoe Chemical Industry Co., Ltd.), Mucor haemelis (e.g., BioAvard® from Indore Biotech Inputs & Research), Muscodor albus (e.g., strain QST 20799), Myrothecium verrucaria (e.g., "DiTera™" manufactured by Valent Biosciences using strain AARC-0255), Paecilomyces fumosoroseus (e.g., "PreFeRal™ WG" manufactured by Biobest using strain apopka 97, "Preferred Wettable Powder" manufactured by Tokai Bussan Co., Ltd., "No Fly™" manufactured by Natural Industries Inc. (Novozymes company) using strain FE9901), Paecilomyces lilacinus (e.g., "BioAct WG™" manufactured by Prophyta using strain 251),

[0223] Paecilomyces tenuipes (e.g., Gotz A® manufactured by Idemitsu Kosan Co., Ltd. using strain T1), Paecilomyces variotii (e.g., Nemaquim® manufactured by Quimia, MX using strain Q-09), Paenibacillus polymyxa (e.g., Topseed® manufactured by Green Biotech Company Ltd. using strain AC-1), Paenibacillus poppiliae (e.g., Milky spore disease® manufactured by St. Gabriel Laboratories), Pasteuria nishizawae (e.g., Pasteuria "oyacystLF / ST (registered trademark)" manufactured by Pasteuria Bioscience, and "Clariva pn" manufactured by Syngenta using strain Pn1), Pasteuria penetrans (e.g., "Pasteuria (registered trademark)" manufactured by Pasteuria Bioscience), Pasteuria usagae (e.g., "Econem (registered trademark)" manufactured by Pasteuria Bioscience),

[0224] Pantoea agglomerans (e.g., Bloomtime Biological FD Biopesticide manufactured by Nufarm US using strain E325), Pectobacterium carotovorum (e.g., Biokeeper manufactured by Nissan Chemical Co., Ltd. and Ecomate manufactured by Kumiai Chemical Co., Ltd. using strain CGE234M403), Phoma macrostroma (e.g., Phoma H manufactured by Scotts, US using strain 94-44B), Penicillium bilaii (e.g., Jump Start manufactured by Novozymes), Phlebiopsis gigantea (e.g., strain FOC PG B22 / SP1190 / 3.2 (ROTSOP® from Verdera, Finland), Pochonia chlamydosporia var. catenulata (e.g., The National Center of Animal and Plant Health (CENSA);Pseudomonas aureofaciens (e.g., Spot-Less Biofungicide® from EcoSoils Systems, CA using strain TX-1), Pseudomonas chlororaphis (e.g., ATEze® from EcoSoil Systems using strain 63-28 or Cedomon® from Bioagri, S using strain MA342), Pseudomonas fluorescens (e.g., Frostban® from Frost Technology Corp using strain 1629RS), D (registered trademark), "Blightban (registered trademark)" manufactured by "Blightban" using strain A506, "Konae Fukudo (registered trademark)" manufactured by "Taki Chemical Co., Ltd." using strain FPT-9601, "Cell Nae Genki (registered trademark)" manufactured by "Taki Chemical Co., Ltd." which is a mixture of strains FPT-9601 and FPH-9601, "Vegetable Keeper (registered trademark)" manufactured by "Arysta Life Sciences Inc." using strain G7090), Pseudomonas proradix (for example, [Proradix (registered trademark] manufactured by "Sourcon Padena");

[0225] Pseudomonas resinovorans (e.g., Solanacure® from Agricultural Research Council, SA), Pseudomonas syringae (e.g., Biosave® from EcoScience, US using strain MA-4, Frostban C from Frost Technology Corp® using strain 742RS, Bio-save 10LP Biological Fungicide from Jet Harvest Systems using strain ESC10, and Bio-Save 11 LP Biological Fungicide from Jet Harvest Systems using strain ESC11), Pseudomonas spp.) (for example, "Masterpiece Wettable Powder (registered trademark)" manufactured by Nippon Soda Co., Ltd. using strain HAI-0804, and "Momigenki Wettable Powder (registered trademark)" manufactured by Nissan Chemical Industries, Ltd. using strain CAB-02), Pseudozyma aphidis (for example, manufactured by Yissum Research Development Company of the Hebrew University of Jerusalem), Pseudozyma flocculosa (for example, "Sporodex L (registered trademark)" manufactured by Plant Products Co. Ltd, CA using strain PF-A22 UL), Pythium oligandrum (for example, "Polyversum (registered trademark)" manufactured by Bioprepraty, CZ using strain DV74 or M1), Reynoutria sacrinensis sachlinensis) (e.g., REGALIA (registered trademark) manufactured by Marrone BioInnovations, US),

[0226] Rhizopogon amylopogon (e.g., Myco-Sol® from Helena Chemical Company), Rhizopogon fulvigleba (e.g., Myco-Sol® from Helena Chemical Company), Saccharomyces cerevisiae (e.g., Lesaffre et Compagnie, FR), Sclerotinia minor (e.g., Sarritor® from Agrium Advanced Technologies), Serratia entomophila (e.g., Invade® from Wrightson Seeds), Sporothrix insectorum (e.g., Sporothrix Es (registered trademark)"), Steinernema carpocapsae (e.g., Biosafe (registered trademark) manufactured by SDS Biotech Co., Ltd.), Steinernema kushidai (e.g., Shibaichinema manufactured by Kubota Corporation), Steinernema glaseri (e.g., Biotopia (registered trademark) manufactured by Arista Life Sciences Co., Ltd.), Streptomyces acidiscabies (e.g., MBI-005EP (registered trademark) manufactured by Marrone Bioinnovations, CA using strain RL-110T), Streptomyces candidus (e.g., BioBac (registered trademark) manufactured by Biontech, TW using strain Y21007-2),

[0227] Streptomyces galbus (e.g., Mycostop® manufactured by Verdera, strain K61), Streptomyces lydicus (e.g., ACTINOVATE® manufactured by Natural Industries, US, using strain WYEC108), Streptomyces saraceticus (e.g., Clanda® manufactured by A&A Group (Agro Chemical Corp.)), Talaromyces flavus (e.g., FirKeeper® manufactured by Central Glass Co., Ltd., using strain B-422, ToughBlock® manufactured by Idemitsu Kosan Co., Ltd., using strain SAY-Y-94-01, and PROTUS® manufactured by Prophyta, DE, using strain V117b). WG), Trichoderma asperellum (e.g., Isagro using strain ICC 012, T34 Biocontrol® using strain T34 from Biocontrol Technologies, ES, ECO-HOPE® using strain SKT-1 from Kumiai Chemical Industry Co., Ltd.), Trichoderma atroviride (e.g., Esquive® WP from Agrauxine, FR, Tenet® or SENTINEL® using strain LC52 from Agrimm Technologies Ltd, NZ, ECO-HOPE DJ® using strain SKT-1 from Kumiai Chemical Industry Co., Ltd.), Trichoderma gamsii (e.g., Bayer "BIO-TAM™ (registered trademark)" manufactured by CropScience LP, US

[0228] Trichoderma harzianum (e.g., T-Gro 7456 (registered trademark) manufactured by Dagutat Biolab using strain DB103, Trianum-P (registered trademark) manufactured by Koppert using strain ITEM908, Trichoplus (registered trademark) manufactured by Biological Control Products, SA using strain KD, and ROOT PRO (registered trademark) manufactured by Mycontrol Ltd. using strain TH-35), Trichoderma harzianum rifai (e.g., PLANTSHIELD T-22G (registered trademark) manufactured by Firma BioWorks Inc. US using strain T-22 and TRICHODEX (registered trademark) manufactured by Makhteshim Ltd, US using strain T-39), Trichoderma lignorm (e.g., Trichoderma lignorum (e.g., Mycotric® from Futureco Bioscience, ES using strain TL-0601), Trichoderma polysporum (e.g., Binab TF WP® from BINAB Bio-Innovation AB, Sweden), Trichoderma stromaticum (e.g., TRICOVAB® from Ceplac, Brazil), Trichoderma virens (e.g., SOILGARD® from Certis LLC, US using strain GL-21),

[0229] Trichoderma viride (e.g., REMEDIER® WP manufactured by Isagro Ricerca, ITALY using the strain ICC080 and Trianum-P® manufactured by Koppert using the strain TV1), Tsukamurella paurometabola (e.g., HeberNem® manufactured by the strain C-924), Ulocladium oudemansii (e.g., Botry-Zen Ltd. using the strain HRU3),NZ's "Botry-Zen®" and "BotryStop" manufactured by BioWorks Inc. using strain U3), Variovorax paradoxus (e.g., "Field Keeper Wettable Powder®" manufactured by Central Glass using strain CGF4526), ​​VA (Vesicular-Arbuscular Mycorrhiza) mycorrhizal fungi (e.g., "Dr. Kinkon®" manufactured by Idemitsu Agri), Verticillium alboatrum (e.g., "Dutch Trig®" manufactured by Tree Care Innovations using strain WCS850), Verticillium lecanii (e.g., "Vertalec®" manufactured by Arysta Life Sciences Inc. using strain IMI 179172 and "BotryStop" manufactured by BioWorks Inc. using strain IMI 179172), 263817), Xanthomonas campestris (for example, "Camperico Liquid" manufactured by Taki Chemical Co., Ltd.), Xanthomonas campestris pv. poae, Heterorhabditis bacteriophora, Steinernema feltiae, Steinernema kraussei, Steinernema riobrave, Steinernema scapterici, scapterisci), or mutants of these strains that possess all of the distinguishing characteristics of the respective strains, or metabolites produced by the respective strains that exhibit activity against plant pathogenic fungi.

[0230] Representative examples of the present invention will be given below, but the present invention is not limited to these.

[0231] Production Example 1 Production of 1-tert-butyl-3-{6-[3-(2-chlorophenyl)-5-methyl-1H-1,2,4-triazol-1-yl]-5-(methanesulfonyl)pyridin-2-yl}imidazolidin-2-one (Compound No. 1-1) To a solution of 1-[6-bromo-5-(methanesulfonyl)pyridin-2-yl]-3-tert-butylimidazolidin-2-one (60 mg, 0.16 mmol) produced by the method described in Reference Production Example 1 below in N,N-dimethylacetamide (1.5 mL), potassium carbonate (44 mg, 0.32 mmol) and 3-(2-chlorophenyl)-5-methyl-1H-1,2,4-triazole (31 mg, 0.16 mmol) were added, and the mixture was stirred at 130°C for 5 hours. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate, and the organic layer was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to give 1-tert-butyl-3-{6-[3-(2-chlorophenyl)-5-methyl-1H-1,2,4-triazol-1-yl]-5-(methanesulfonyl)pyridin-2-yl}imidazolidin-2-one (63 mg, 0.13 mmol). Yield: 81% Physical properties: １ H-NMR (CDCl ３ ):δ 8.63 (d, 1H), 8.37 (d, 1H), 8.05-8.03 (m, 1H), 7.49-7.47 (m, 1H), 7.38-7.3 4 (m, 2H), 3.95 (t, 2H), 3.57 (t, 2H), 3.43 (s, 3H), 2.55 (s, 3H), 1.46 (s, 9H)

[0232] Production Example 2 Production of 6-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)-N-methyl-2-(1-methyl-3-phenyl-1H-1,2,4-triazol-5-yl)pyridine-3-sulfonamide (Compound No. 2-9) To a solution of 6-chloro-N-methyl-2-(1-methyl-3-phenyl-1H-1,2,4-triazol-5-yl)pyridine-3-sulfonamide (0.20 g, 0.55 mmol) prepared by the method described in Reference Production Example 2 below in N,N-dimethylacetamide (3.0 mL), 3,5-dimethyl-1H-1,2,4-triazole (81 mg, 0.83 mmol) and cesium carbonate (0.55 g, 1.7 mmol) were added and the mixture was stirred at 100°C for 2 hours. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate, and the organic layer was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to give 6-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)-N-methyl-2-(1-methyl-3-phenyl-1H-1,2,4-triazol-5-yl)pyridine-3-sulfonamide (65 mg, 0.15 mmol). Yield: 28% Physical properties: １ H-NMR (CDCl ３ ):δ 8.61 (d, 1H), 8.21 (d, 1H), 8.02-7.99 (m, 1H), 7.92-7.87 (m, 1H), 7.43-7. 40 (m, 2H), 7.34-7.29 (m, 1H), 4.08 (s, 3H), 2.86-2.82 (m, 6H), 2.45 (s, 3H)

[0233] Production Example 3 Production of N-methyl-6-(1-methyl-1H-pyrazol-5-yl)-2-[1-methyl-3-(thiophen-2-yl)-1H-1,2,4-triazol-5-yl]pyridine-3-sulfonamide (Compound No. 2-160) 6-chloro-N-methyl-2-[1-methyl-3-(thiophen-2-yl)-1H-1,2,4-triazol-5-yl]pyridine-3-sulfonamide (74 mg, 0.20 mmol) produced by the method described in Reference Production Example 6 below was dissolved in a mixed solution of 1,4-dioxane (1.0 mL) and water (0.20 mL), and 1-methyl-1H-pyrazole-5-boronic acid pinacol ester (62 mg, 0.30 mmol), tetrakistriphenylphosphine palladium (23 mg, 20 μmol), and potassium carbonate (98 mg, 0.46 mmol) were added, followed by stirring for 3 hours at 110° C. Water was added to the reaction solution, which was then extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to give N-methyl-6-(1-methyl-1H-pyrazol-5-yl)-2-[1-methyl-3-(thiophen-2-yl)-1H-1,2,4-triazol-5-yl]pyridine-3-sulfonamide (76 mg, 0.18 mmol). Yield: 91%. Physical properties: melting point: 205-207°C.

[0234] Production Example 4 Production of 6-[(3,5-dimethyl-1H-1,2,4-triazol-1-yl)methoxy]-2-(1-ethyl-3-phenyl-1H-1,2,4-triazol-5-yl)-N-methylpyridine-3-sulfonamide (Compound No. 2-174) To a solution of 6-chloro-2-(1-ethyl-3-phenyl-1H-1,2,4-triazol-5-yl)-N-methylpyridine-3-sulfonamide (0.38 g, 1.0 mmol) produced by the method described in Reference Production Example 7 below in acetonitrile (10 mL) were added (3,5-dimethyl-1H-1,2,4-triazol-1-yl)methanol (0.19 g, 1.5 mmol) and cesium carbonate (0.98 g, 3.0 mmol), and the mixture was stirred for 3 hours at 70° C. Water was added to the reaction solution, which was extracted with ethyl acetate, and the organic layer was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to give 6-[(3,5-dimethyl-1H-1,2,4-triazol-1-yl)methoxy]-2-(1-ethyl-3-phenyl-1H-1,2,4-triazol-5-yl)-N-methylpyridine-3-sulfonamide (0.12 g, 0.26 mmol). Yield: 26%. Physical properties: １ H-NMR (CDCl ３ ):δ 8.60 (d, 1H), 8.19 (d, 1H), 8.06-7.97 (m, 2H), 7.50-7.40 (m, 3H), 7.35- 7.28 (m, 1H), 4.40 (q, 2H), 2.84-2.81 (m, 6H), 2.44 (d, 3H), 1.49 (t, 3H)

[0235] Production Example 5 Production of 2-[3-(2-chlorophenyl)-5-methyl-1H-1,2,4-triazol-1-yl]-6-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)-N-methylpyridine-3-sulfonamide (Compound No. 3-2) To a solution of 2-chloro-6-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)-N-methylpyridine-3-sulfonamide (1.0 g, 3.3 mmol) produced by the method described in Reference Production Example 3 below in N,N-dimethylacetamide (10 mL) were added 3-(2-chlorophenyl)-5-methyl-1H-1,2,4-triazole (0.96 g, 5.0 mmol) and potassium carbonate (2.0 g, 15 mmol), and the mixture was stirred for 2 hours at 100° C. Water was added to the reaction solution, which was extracted with ethyl acetate, and the organic layer was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to give 2-[3-(2-chlorophenyl)-5-methyl-1H-1,2,4-triazol-1-yl]-6-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)-N-methylpyridine-3-sulfonamide (0.23 g, 0.50 mmol). Yield: 15%. Physical properties: １ H-NMR (CDCl ３ ):δ 8.63 (d, 1H), 8.26-8.20 (m, 2H), 7.52-7.48 (m, 1H), 7.45-7.36 (m, 2H), 6.66 (q, 1H), 2.83 (s, 3H), 2.77 (d, 3H), 2.66 (s, 3H), 2.45 (s, 3H)

[0236] Production Example 6 Production of 6-[(3,5-dimethyl-1H-pyrazol-1-yl)methoxy]-N-methyl-2-(5-methyl-3-phenyl-1H-pyrazol-1-yl)pyridine-3-sulfonamide (Compound No. 3-36) To a solution of 6-(methanesulfonyl)-N-methyl-2-(5-methyl-3-phenyl-1H-pyrazol-1-yl)pyridine-3-sulfonamide (35 mg, 0.086 mmol) produced by the method described in Reference Production Example 4 below in acetonitrile (2.0 mL), 1-(hydroxymethyl)-3,5-dimethylpyrazole (11 mg, 0.087 mmol) and potassium carbonate (24 mg, 0.17 mmol) were added, and the mixture was stirred at 60°C for 6 hours. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate, and the organic layer was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to give 6-[(3,5-dimethyl-1H-pyrazol-1-yl)methoxy]-N-methyl-2-(5-methyl-3-phenyl-1H-pyrazol-1-yl)pyridine-3-sulfonamide (32 mg, 0.071 mmol). Yield: 80%. Properties: １ H-NMR (CDCl ３ ):δ 8.38 (d, 1H), 7.73-7.70 (m, 2H), 7.45-7.35 (m, 3H), 6.96 (d, 1H), 6.62 (q, 1H), 6.60 ( s, 1H), 6.19 (s, 2H), 5.91 (s, 1H), 2.76 (d, 3H), 2.48 (s, 3H), 2.30 (s, 3H), 2.24 (s, 3H)

[0237] Production Example 7 Production of 6-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)-N-methyl-2-(1-methyl-4-phenylimidazol-2-yl)pyridine-3-sulfonamide (Compound No. 2-16) To a solution of 6-chloro-N-methyl-2-(1-methyl-4-phenyl-1H-imidazol-2-yl)pyridine-3-sulfonamide (82 mg, 0.22 mmol) prepared by the method described in Reference Production Example 5 below in N,N-dimethylacetamide (2.0 mL), 3,5-dimethyl-1H-1,2,4-triazole (32 mg, 0.33 mmol) and cesium carbonate (0.22 g, 0.66 mmol) were added, and the mixture was stirred at 100°C for 2 hours. Water was added to the reaction solution, and the resulting solid was collected by filtration to give 6-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)-N-methyl-2-(1-methyl-4-phenylimidazol-2-yl)pyridine-3-sulfonamide (32 mg, 0.076 mmol). Yield: 34%. Physical properties: Melting point: 134-135°C.

[0238] Reference Preparation Example 1 Preparation of 1-[6-bromo-5-(methanesulfonyl)pyridin-2-yl]-3-tert-butylimidazolidin-2-one To a solution (11 mL) of 1-(1,1-dimethylethyl)-2-imidazolidinone (0.32 g, 2.3 mmol) in toluene and dimethyl sulfoxide, sodium hydride (60% wt, 0.11 g, 2.8 mmol) was added in an ice bath and stirred for 30 minutes. After that, 2-bromo-6-chloro-3-(methanesulfonyl)pyridine (0.60 g, 2.2 mmol) was added and stirred at 100°C for 7 hours. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate, and the organic layer was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to give 1-[6-bromo-5-(methanesulfonyl)pyridin-2-yl]-3-tert-butylimidazolidin-2-one (0.15 g, 0.40 mmol). Yield: 18%

[0239] Reference Production Example 2: Preparation of 6-chloro-N-methyl-2-(1-methyl-3-phenyl-1H-1,2,4-triazol-5-yl)pyridine-3-sulfonamide Reference Production Example 2-1: Preparation of methyl 3-((4-(tert-butyl)benzyl)thio)-6-chloropicolinate Sodium hydride (60 wt%, 4.70 g, 0.12 mol) was added to a solution of methyl 3,6-dichloropyrrolinate (20 g, 97 mmol) in tetrahydrofuran (0.50 L) in an ice bath and stirred for 15 minutes. Then, (4-(tert-butyl)phenyl)methanethiol (18 mL, 0.10 mol) was added dropwise and stirred at room temperature for 3 hours. A saturated aqueous solution of ammonium chloride was added to the reaction solution in an ice bath, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, concentrated, and the residue was washed with normal hexane to obtain methyl 3-((4-(tert-butyl)benzyl)thio)-6-chloropicolinate (30 g, 86 mmol). Yield: 88%. Physical properties: １ H-NMR (CDCl ３ ): δ 7.66-7.63 (m, 1H), 7.37-7.28 (m, 5H), 4.12 (s, 2H), 3.98 (s, 3H), 1.31 (s, 9H)

[0240] Reference Production Example 2-2 Production of 3-((4-(tert-butyl)benzyl)thio)-6-chloropicolinic acid To a solution of methyl 3-((4-(tert-butyl)benzyl)thio)-6-chloropicolinate (30 g, 86 mmol) in methanol (200 mL) and tetrahydrofuran (50 mL) was added lithium hydroxide (4.3 g, 0.10 mol) at room temperature, and the mixture was stirred at room temperature for 6 hours. The reaction solution was concentrated under reduced pressure, 2 M hydrochloric acid was added, and the resulting solid was collected by filtration and washed with normal hexane to give 3-((4-(tert-butyl)benzyl)thio)-6-chloropicolinic acid (30 g, 85 mmol). Yield: 100%

[0241] Reference Production Example 2-3 Production of 3-((4-(tert-butyl)benzyl)thio)-6-chloro-2-(1-methyl-3-phenyl-1H-1,2,4-triazol-5-yl)pyridine N,N-Diisopropylethylamine (15 mL, 90 mmol) and 1-[bis(dimethylamino)methylene]-1H-benzotriazolium 3-oxide hexafluorophosphate (17 g, 45 mmol) were added to a solution of 3-((4-(tert-butyl)benzyl)thio)-6-chloropicolinic acid (10 g, 30 mmol) and ethyl benzimidate hydrochloride (5.6 g, 30 mmol) in N,N-dimethylformamide (60 mL), and the mixture was stirred overnight at room temperature. Water was added to the reaction solution, which was then extracted with chloroform. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was dissolved in ethanol (60 mL), and methylhydrazine (2.4 mL, 45 mmol) was added, followed by heating to reflux for 2 hours. The residue obtained by concentration under reduced pressure was purified by silica gel column chromatography to give 3-((4-(tert-butyl)benzyl)thio)-6-chloro-2-(1-methyl-3-phenyl-1H-1,2,4-triazol-5-yl)pyridine (2.1 g, 4.6 mmol). Yield: 5%

[0242] Reference Production Example 2-4 Production of 6-chloro-N-methyl-2-(1-methyl-3-phenyl-1H-1,2,4-triazol-5-yl)pyridine-3-sulfonamide Water (0.50 mL, 27 mmol) and acetic acid (0.80 mL, 14 mmol) were added to a solution of 3-((4-(tert-butyl)benzyl)thio)-6-chloro-2-(1-methyl-3-phenyl-1H-1,2,4-triazol-5-yl)pyridine (2.1 g, 4.6 mmol) in chloroform (50 mL), and 1,3-dichloro-5,5-dimethylhydantoin (2.7 g, 14 mmol) was added in an ice bath. After confirming the disappearance of the raw materials, the reaction solution was added dropwise to a methylamine-methanol solution (9.8 mol / L, 20 mL) in an ice bath and stirred for 30 minutes. Saturated aqueous ammonium chloride solution was further added, and the mixture was extracted with ethyl acetate, and the organic layer was concentrated. The residue was purified by silica gel column chromatography to give 6-chloro-N-methyl-2-(1-methyl-3-phenyl-1H-1,2,4-triazol-5-yl)pyridine-3-sulfonamide (0.70 g, 1.9 mmol). Yield: 42%. Physical properties: １H-NMR (CDCl ３ ): δ 8.46 (d, 1H), 8.14 (q, 1H), 8.00-7.95 (m, 2H), 7.59 (d, 1H), 7.50-7.41 (m, 3H), 4.18 (s, 3H), 2.80 (s, 3H)

[0243] Reference Production Example 3: Preparation of 2-chloro-6-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)-N-methylpyridine-3-sulfonamide Reference Production Example 3-1: Preparation of 2,6-dichloro-N-methylpyridine-3-sulfonamide To a solution of 2,6-dichloropyridine-3-sulfonyl chloride in tetrahydrofuran (0.20 L), a 7.0% solution of methylamine in tetrahydrofuran (31 mL, 61 mmol) was added under ice cooling, and the mixture was stirred at room temperature for 1 hour. After completion of the reaction, the reaction solution was extracted with saturated aqueous ammonium chloride and ethyl acetate, the organic layer was dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to give 2,6-dichloro-N-methylpyridine-3-sulfonamide (6.4 g, 27 mmol). Yield: 44%. Physical properties: １ H-NMR (CDCl ３ ): δ 8.35 (d, 1H), 7.46 (d, 1H), 5.10 (br.s, 1H), 2.71 (d, 3H)

[0244] Reference Production Example 3-2 Production of 2-chloro-6-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)-N-methylpyridine-3-sulfonamide To a solution of 2,6-dichloro-N-methylpyridine-3-sulfonamide (5.0 g, 21 mmol) in N,N-dimethylacetamide (42 mL), 3,5-dimethyl-1H-1,2,4-triazole (3.0 g, 31 mmol) and cesium carbonate (14 g, 42 mmol) were added, and the mixture was stirred at 100°C for 2 hours. Water was added to the reaction solution, which was then extracted with ethyl acetate, and the organic layer was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to give 2-chloro-6-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)-N-methylpyridine-3-sulfonamide (1.2 g, 4.0 mmol). Yield: 19%

[0245] Reference Production Example 4: Preparation of 6-(methanesulfonyl)-N-methyl-2-(5-methyl-3-phenyl-1H-pyrazol-1-yl)pyridine-3-sulfonamide Reference Production Example 4-1: Preparation of 2-chloro-N-methyl-6-(methylsulfanyl)pyridine-3-sulfonamide To a solution of 2,6-dichloro-N-methylpyridine-3-sulfonamide (3.4 g, 14 mmol) in N,N-dimethylacetamide (28 mL), methyl mercaptan sodium (1.5 g, 21 mmol) was added and stirred at room temperature for 7 hours. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate, and the organic layer was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to give 2-chloro-N-methyl-6-(methylsulfanyl)pyridine-3-sulfonamide (3.6 g, 14 mmol) as a crude product. Yield: 100%

[0246] Reference Production Example 4-2 Production of 6-N-methyl-2-(5-methyl-3-phenyl-1H-pyrazol-1-yl)-6-(methylsulfanyl)pyridine-3-sulfonamide To a solution of the crude 2-chloro-N-methyl-6-(methylsulfanyl)pyridine-3-sulfonamide (3.4 g, 13 mmol) in N,N-dimethylacetamide (25 mL), 5-methyl-3-phenyl-1H-pyrazole (1.1 g, 7.0 mmol) and potassium carbonate (2.8 g, 20 mmol) were added, and the mixture was stirred at 130°C for 16 hours. Water was added to the reaction mixture, which was then extracted with ethyl acetate, and the organic layer was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to give 6-N-methyl-2-(5-methyl-3-phenyl-1H-pyrazol-1-yl)-6-(methylsulfanyl)pyridine-3-sulfonamide (0.32 g, 0.85 mmol). Yield: 13%

[0247] Reference Production Example 4-3 Production of 6-(methanesulfonyl)-N-methyl-2-(5-methyl-3-phenyl-1H-pyrazol-1-yl)pyridine-3-sulfonamide To a solution of N-methyl-2-(5-methyl-3-phenyl-1H-pyrazol-1-yl)-6-(methylsulfanyl)pyridine-3-sulfonamide (0.32 g, 0.85 mmol) in ethyl acetate (5.0 mL), metachloroperbenzoic acid (30% aqueous, 0.63 g, 2.5 mmol) was added and stirred at room temperature for 6 hours. Saturated aqueous sodium bicarbonate and saturated aqueous sodium thiosulfate were added to the reaction solution, followed by extraction with ethyl acetate, and the organic layer was concentrated under reduced pressure. The resulting residue was purified by column chromatography to give 6-(methanesulfonyl)-N-methyl-2-(5-methyl-3-phenyl-1H-pyrazol-1-yl)pyridine-3-sulfonamide (0.21 g, 0.52 mmol). Yield: 60%

[0248] Reference Production Example 5: Preparation of 6-chloro-N-methyl-2-(1-methyl-4-phenyl-1H-imidazol-2-yl)pyridine-3-sulfonamide Reference Production Example 5-1: Preparation of 2-oxo-2-phenylethyl 3-((4-(tert-butyl)benzyl)thio)-6-chloropicolinate Phenacyl chloride (3.0 g, 20 mmol) and N,N-diisopropylethylamine (8.3 mL, 49 mmol) were added to a solution of 3-((4-(tert-butyl)benzyl)thio)-6-chloropicolinic acid (6.6 g, 20 mmol) in N,N-dimethylformamide (28 mL) under ice-cooling, and the mixture was stirred overnight at room temperature. After completion of the reaction, the reaction solution was extracted with water and ethyl acetate, and the organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure to obtain crude 2-oxo-2-phenylethyl 3-((4-(tert-butyl)benzyl)thio)-6-chloropicolinate (7.8 g, 17 mmol). Yield: 88%

[0249] Reference Production Example 5-2 Production of 3-((4-(tert-butyl)benzyl)thio)-6-chloro-2-(4-phenyl-1H-imidazol-2-yl)pyridine Ammonium acetate (27 g, 0.34 mol) was added to a solution of 2-oxo-2-phenylethyl 3-((4-(tert-butyl)benzyl)thio)-6-chloropicolinate (7.8 g, 17 mmol) in acetic acid (86 mL), and the mixture was stirred under heating under reflux. The reaction mixture was concentrated under reduced pressure and extracted with saturated aqueous sodium bicarbonate and ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to give 3-((4-(tert-butyl)benzyl)thio)-6-chloro-2-(4-phenyl-1H-imidazol-2-yl)pyridine (7.4 g, 17 mmol). Yield: 99%

[0250] Reference Production Example 5-3 Production of 3-((4-(tert-butyl)benzyl)thio)-6-chloro-2-(1-methyl-4-phenyl-1H-imidazol-2-yl)pyridine To a solution of 3-((4-(tert-butyl)benzyl)thio)-6-chloro-2-(4-phenyl-1H-imidazol-2-yl)pyridine (7.4 g, 17 mmol) in tetrahydrofuran (90 mL) were added potassium tert-butoxide (2.1 g, 18.8 mmol) and iodomethane (1.2 mL, 19 mmol) under ice-cooling, and the mixture was stirred at room temperature for 2 hours. Saturated aqueous ammonium chloride solution and ethyl acetate were added to the reaction solution for extraction, and the organic layer was dried over sodium sulfate and concentrated. The residue was purified by silica gel column chromatography to give 3-((4-(tert-butyl)benzyl)thio)-6-chloro-2-(1-methyl-4-phenyl-1H-imidazol-2-yl)pyridine (4.6 g, 10 mmol). Yield: 59%

[0251] Reference Production Example 5-4 Production of 6-chloro-N-methyl-2-(1-methyl-4-phenyl-1H-imidazol-2-yl)pyridine-3-sulfonamide To a solution of 3-((4-(tert-butyl)benzyl)thio)-6-chloro-2-(1-methyl-4-phenyl-1H-imidazol-2-yl)pyridine (2.0 g, 4.5 mmol) in chloroform (50 mL) were added water (0.50 mL, 27 mmol) and acetic acid (0.77 mL, 13 mmol), and 1,3-dichloro-5,5-dimethylhydantoin (2.6 g, 13 mmol) was added in an ice bath. After confirming the disappearance of the raw materials, the reaction mixture was added dropwise to a methylamine-methanol solution (30 mL) in an ice bath and stirred for 30 minutes. A saturated aqueous ammonium chloride solution was added, and the mixture was extracted with ethyl acetate, and the organic layer was concentrated. The residue was purified by silica gel column chromatography to give 6-chloro-N-methyl-2-(1-methyl-4-phenyl-1H-imidazol-2-yl)pyridine-3-sulfonamide (0.51 mg, 1.4 mmol). Yield: 31% Physical properties: １ H-NMR (CDCl ３ ): δ 8.95 (q, 1H), 8.42 (d, 1H), 7.67-7.63 (m, 2H), 7.48-7.38 (m, 3H), 7.33-7.29 (m, 2H), 3.97 (s, 3H), 2.78 (d, 3H)

[0252] Reference Production Example 6: Preparation of 6-chloro-N-methyl-2-[1-methyl-3-(thiophen-2-yl)-1H-1,2,4-triazol-5-yl]pyridine-3-sulfonamide Reference Production Example 6-1: Preparation of ethyl thiophene-2-carboxyimidate hydrochloride Acetyl chloride (33 mL, 0.46 mol) was added dropwise to a solution of thiophene-2-carbonitrile (5.0 g, 46 mmol) in ethanol (28 mL) in an ice bath. The reaction mixture was stirred at room temperature for 72 hours, then concentrated under reduced pressure. The resulting residue was washed with hexane to give ethyl thiophene-2-carboxyimidate hydrochloride (8.3 g, 43 mmol) as a crude product. Yield: 95%

[0253] Reference Production Example 6-2 Production of N'-methylthiophene-2-carbohydrazonamide hydrochloride To a solution of ethyl thiophene-2-carboxyimidate hydrochloride (4.0 g, 21 mmol) in methanol (20 mL) was added 1-methylhydrazine (1.3 mL, 25 mmol), and the mixture was stirred at room temperature for 18 hours. The reaction mixture was concentrated under reduced pressure, and the resulting residue was washed with methyl tert-butyl ether to give N'-methylthiophene-2-carbohydrazonamide hydrochloride as a crude product.

[0254] Reference Production Example 6-3 Production of 6-chloro-N-methyl-2-[1-methyl-3-(thiophen-2-yl)-1H-1,2,4-triazol-5-yl]pyridine-3-sulfonamide N'-methylthiophene-2-carbohydrazonamide hydrochloride (1.4 g, 7.3 mmol) and 5-chloro-2-methyl-1H-1λ prepared by the method described in Reference Preparation Example 8 or 9 below. ６To a solution of 1,3-[1,2]thiazolo[4,5-b]pyridine-1,1,3(2H)-trione (1.3 g, 5.8 mmol) in toluene (10 mL), sodium acetate (0.60 g, 7.5 mmol) was added and the mixture was heated to reflux for 6 hours. The reaction solution was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography to give 6-chloro-N-methyl-2-[1-methyl-3-(thiophen-2-yl)-1H-1,2,4-triazol-5-yl]pyridine-3-sulfonamide (0.96 g, 2.6 mmol). Yield: 44%. Physical properties: １ H-NMR (CDCl ３ ): δ 8.45 (d, 1H), 7.91-7.86 (m, 1H), 7.63-7.61 (m, 1H), 7.59 (d, 1H), 7.40-7.37 (m, 1H), 7.13-7.10 (m, 1H), 4.16 (s, 3H), 2.80 (d, 3H).

[0255] Reference Production Example 7: Preparation of 6-chloro-2-(1-ethyl-3-phenyl-1H-1,2,4-triazol-5-yl)-N-methylpyridine-3-sulfonamide Reference Production Example 7-1: Preparation of N'-ethylbenzenecarbohydrazonamide hydrochloride To a solution (15 mL) of benzenecarboximidamide hydrochloride (5.0 g, 32 mmol) in methanol, 1-ethylhydrazine (1.8 mL, 38 mmol) was added and the mixture was stirred at room temperature for 18 hours. The reaction mixture was concentrated under reduced pressure, and the resulting residue was washed with hexane to give N'-ethylbenzenecarbohydrazonamide hydrochloride as a crude product.

[0256] Reference Production Example 7-2 Production of 6-chloro-2-(1-ethyl-3-phenyl-1H-1,2,4-triazol-5-yl)-N-methylpyridine-3-sulfonamide N'-ethylbenzenecarbohydrazonamide hydrochloride (5.0 g, 25 mmol) and 5-chloro-2-methyl-1H-1λ prepared by the method described in Reference Preparation Example 8 or 9 below. ６To a solution of 1,2-thiazolo[4,5-b]pyridine-1,1,3(2H)-trione (4.5 g, 19 mmol) in acetic acid (10 mL) and toluene (10 mL) was added sodium acetate (5.3 g, 64 mmol), and the mixture was heated to reflux for 3 hours. The reaction mixture was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography to give 6-chloro-2-(1-ethyl-3-phenyl-1H-1,2,4-triazol-5-yl)-N-methylpyridine-3-sulfonamide (2.6 g, 13 mmol). Yield: 36%. Physical properties: １ H-NMR (CDCl ３ ): δ 8.45 (d, 1H), 8.07-8.02 (m, 1H), 8.02-7.95 (m, 2H), 7.60 (d, 1H), 7.49-7.42 (m, 3H), 4.48 (q, 2H), 2.80 (d, 3H), 1.58 (t, 3H)

[0257] Reference Production Example 8 5-chloro-2-methyl-1H-1λ ６ Preparation of -[1,2]thiazolo[4,5-b]pyridine-1,1,3(2H)-trione Reference Preparation Example 8-1 Preparation of 6-chloro-N-methyl-3-(methylsulfanyl)pyridine-2-carboxamide To a solution of methyl 6-chloro-3-(methylsulfanyl)pyridine-2-carboxylate (50 g, 0.23 mol) in methanol (0.40 L), a solution of methylamine in methanol (70 mL, 9.8 mol / L, 0.69 mol) was added at room temperature and stirred overnight. The reaction solution was concentrated under reduced pressure, and then hexane was added. The precipitated solid was collected by filtration to obtain 6-chloro-N-methyl-3-(methylsulfanyl)pyridine-2-carboxamide (50 g, 0.23 mol). Yield: 100%. Physical properties: １ H-NMR (DMSO-d ６ ): δ 8.54 (s, 1H), 7.86 (d, 1H), 7.63 (d, 1H), 2.77 (d, 3H), 2.39 (s, 3H)

[0258] Reference Production Example 8-2 Production of 5-chloro-2-methyl[1,2]thiazolo[4,5-b]pyridin-3(2H)-one To a solution of 6-chloro-N-methyl-3-(methylsulfanyl)pyridine-2-carboxamide (10 g, 46 mmol) in chloroform (90 mL) was added dropwise sulfuryl chloride (6.3 mL, 50 mmol) at room temperature, and the mixture was stirred at room temperature for 30 minutes and then at 50° C. for 30 minutes. Methyl tert-butyl ether was added to the reaction solution, and the precipitated solid was collected by filtration to give 5-chloro-2-methyl[1,2]thiazolo[4,5-b]pyridin-3(2H)-one (7.1 g, 35 mmol). Yield: 76%. Physical properties: １ H-NMR (CDCl ３ ): δ 7.95 (d, 1H), 7.55 (d, 1H), 3.51 (s, 3H)

[0259] Reference Production Example 8-3 5-chloro-2-methyl-1H-1λ ６ Preparation of -[1,2]thiazolo[4,5-b]pyridine-1,1,3(2H)-trione To a solution of 5-chloro-2-methyl[1,2]thiazolo[4,5-b]pyridin-3(2H)-one (6.6 g, 33 mmol) in ethyl acetate (100 mL), metachloroperbenzoic acid (20.4 g, 83 mmol) was added at 0°C and stirred overnight at room temperature. A saturated aqueous solution of sodium bicarbonate and a saturated aqueous solution of sodium thiosulfate were added to the reaction solution. This was extracted with ethyl acetate, dried over sodium sulfate, and then concentrated under reduced pressure to give 5-chloro-2-methyl-1H-1λ ６ -[1,2]thiazolo[4,5-b]pyridine-1,1,3(2H)-trione (6.5 g, 28 mmol) was obtained. Yield: 85%. Physical properties: １ H-NMR (CDCl ３ ): δ 8.24 (d, 1H), 7.80 (d, 1H), 3.34 (s, 3H)

[0260] Reference Production Example 9 (alternative to Reference Production Example 8) 5-chloro-2-methyl-1H-1λ ６ Preparation of -[1,2]thiazolo[4,5-b]pyridine-1,1,3(2H)-trione Reference Preparation Example 9-1 Preparation of 6-chloro-3-(methylsulfamoyl)pyridine-2-carboxylic acid To a solution of 6-chloro-N-methyl-3-(methylsulfanyl)pyridine-2-carboxamide (5.0 g, 24 mmol) in chlorobenzene (50 mL) was added water (1.3 mL, 73 mmol), and sulfuryl chloride (6.0 mL, 73 mmol) was added dropwise at room temperature, followed by stirring at 70° C. for 90 minutes. Methyl tert-butyl ether was added to the reaction solution, and the precipitated solid was collected by filtration to obtain 6-chloro-3-(methylsulfamoyl)pyridine-2-carboxylic acid (5.1 g, 20 mmol). Yield: 83%. Physical properties: １ H-NMR (DMSO-d ６ ): δ 8.22-8.16 (brs, 1H), 8.13 (d, 1H), 7.54 (d, 1H), 2.71 (d, 3H)

[0261] Reference Production Example 9-2 5-chloro-2-methyl-1H-1λ ６ Preparation of -[1,2]thiazolo[4,5-b]pyridine-1,1,3(2H)-trione To a suspension of 6-chloro-3-(methylsulfamoyl)pyridine-2-carboxylic acid (1.0 g, 4.0 mmol) in toluene (0.87 mL), N,N-dimethylformamide (70 mg, 1.0 mmol) and thionyl chloride (0.87 mL, 12 mmol) were added at room temperature, and the mixture was stirred at 80°C. Water was added to the reaction mixture at room temperature, and the mixture was extracted with ethyl acetate, dried over sodium sulfate, and then concentrated under reduced pressure. The resulting residue was washed with ethanol and collected by filtration to give 5-chloro-2-methyl-1H-1λ ６ -[1,2]thiazolo[4,5-b]pyridine-1,1,3(2H)-trione (0.75 g, 3.2 mmol) was obtained. Yield: 81%. Physical properties: １ H-NMR (CDCl ３ ): δ 8.24 (d, 1H), 7.80 (d, 1H), 3.34 (s, 3H)

[0262] Examples of formulations containing the compound of the present invention are shown below, but the present invention is not limited to these. In the formulation examples, parts indicate parts by weight.

[0263] Formulation Example 1 Compound of the present invention 10 parts Xylene 70 parts N-methylpyrrolidone 10 parts Mixture of polyoxyethylene nonylphenyl ether and calcium alkylbenzenesulfonate 10 parts The above ingredients are mixed and dissolved uniformly to prepare an emulsifiable concentrate.

[0264] Formulation Example 2: Compound of the present invention 3 parts Clay powder 82 parts Diatomaceous earth powder 15 parts The above ingredients are uniformly mixed and pulverized to give a dust.

[0265] Formulation Example 3 Compound of the present invention 5 parts Mixed powder of bentonite and clay 90 parts Calcium lignosulfonate 5 parts The above ingredients are uniformly mixed, and an appropriate amount of water is added, followed by kneading, granulation and drying to give granules.

[0266] Formulation Example 4: Compound of the present invention 20 parts Kaolin and synthetic highly dispersed silicic acid 75 parts Mixture of polyoxyethylene nonylphenyl ether and calcium alkylbenzenesulfonate 5 parts The above ingredients are uniformly mixed and pulverized to give a wettable powder.

[0267] Test Example 1. Test of herbicidal effect on post-emergence paddy field weeds Barnyard grass (Echinochloa crus-galli) was sown in a test tube containing a hydroponic solution and grown in an artificial growth chamber. After that, a chemical agent containing the compound of the present invention as an active ingredient, prepared according to Formulation Example 1, was diluted with water to a predetermined active ingredient concentration and applied dropwise. The plants were then grown in an artificial growth chamber at 30°C under full light conditions. Six days after the chemical agent treatment, the herbicidal effect was evaluated in comparison with an untreated plot according to the following criteria. Criteria for judging herbicidal effect (degree of growth inhibition) and phytotoxicity: 4 points: 90% to 100% herbicidal effect; 3 points: 70% to 89% herbicidal effect; 2 points: 40% to 69% herbicidal effect; 1 point: 1% to 39% herbicidal effect; 0 point: 0% herbicidal effect.

[0268] As a result, in Test Example 1, among the compounds represented by general formula (I) of the present invention, compound numbers 1-1, 2-1, 2-2, 2-3, 2-4, 2-5, 2-6, 2-7, 2-8, 2-9, 2-11, 2-12, 2-13, 2-14, 2-15, 2-16, 2-17, 2-18, 2-19, 2-20, 2-21, 2-22, 2-23, 2-25, 2-26, 2-27, 2-28, 2-29, 2-30, 2-31, 2-32, 2-33, 2-34, 2-35, 2-36, 2-37, 2-38, 2-39, 2-40, 2-41, 2-42, 2-43, 2-44, 2-45, 2-46, 2-47, 2-48, 2-49, 2-50, 2-51, 2-52, 2-53, 2-54, 2-55, 2-56, 2-57, 2-58, 2-59, 2-60, 2-61, 2-62, 2-63, 2-64, 2-65, 2-66, 2-67, 2-68, 2-69, 2-70, 2-71, 2-72, 2-73, 2-74, 2-75, 2-76, 2-77, 2-78, 2-79, 2-80, 2-81, 2-82, 2-83, 2 -26, 2-27, 2-28, 2-29, 2-30, 2-31, 2-32, 2-33, 2-42, 2-43, 2-44, 2-45, 2-47, 2-48, 2-49, 2-51, 2-52, 2-53, 2-54, 2-56, 2-57, 2-58, 2-59, 2-60, 2-61, 2-62, 2-63, 2-64, 2-65, 2-66, 2-67, 2-68 , 2-69, 2-70, 2-71, 2-72, 2-73, 2-75, 2-76, 2-77, 2-78, 2-79, 2-80, 2-81, 2-84, 2-85, 2-86, 2-87, 2-88, 2-89, 2-90, 2-91, 2-92, 2-93, 2-94, 2-95, 2-99, 2-101, 2-103, 2-104, 2-105, 2-106, 2- The compounds 107, 2-110, 2-111, 2-113, 2-171, 2-174, 2-176, 2-178, 2-182, 2-185, 2-186, 2-187, 2-188, 2-199, 3-1, 3-2, 3-3, 3-7, 3-8, 3-13, 3-14 and 3-25 showed herbicidal effects of 3 points or more according to the above criteria at an active ingredient concentration of 10 ppm.

[0269] The compound of the present invention represented by the general formula (I) or a salt thereof has excellent effects as an agricultural and horticultural herbicide.

Claims

1. General formula (I): {In the formula, R １ (a1) (C １ -C ６ (a2) halo(C １ -C ６ ) alkyl group; or (a3) ​​N(R ２ａ ) R ２ｂ Group (wherein, R ２ａ and R ２ｂ (b1) a hydrogen atom, (b2) (C １ -C ６ ) alkyl group, (b3) (C ２ -C ６ ) an alkenyl group, (b4) (C ２ -C ６ ) an alkynyl group, (b5) (C ３ -C ６ ) cycloalkyl group, (b6) halo(C １ -C ６ ) alkyl group, (b7) (C １ -C ７ ) alkylcarbonyl group, (b8) (C １ -C ６ ) alkoxycarbonyl group, (b9) halo(C １ -C ７ ) alkylcarbonyl group, or (b10) halo(C １ -C ６ ) an alkoxycarbonyl group; R ２ａ and R ２ｂ may be the same or different. Het represents the formula (Het-1) or the formula (Het-2). (In the formula, R ３ (c1) a halogen atom; (c2) a cyano atom; (c3) (C １ -C ６ ) alkyl group; (c4) (C ２ -C ６ ) alkenyl group; (c5) (C ２ -C ６ ) an alkynyl group; (c6) (C ３ -C ６ ) cycloalkyl group; (c7) (C １ -C ６ ) alkoxy group; (c8) halo(C １ -C ６ (c9) halo(C ２ -C ６ ) alkenyl group; (c10) halo(C ２ -C ６ ) alkynyl group; (c11) halo(C ３ -C ６ ) cycloalkyl group; (c12) halo(C １ -C ６ (c13) a substituted (C ) alkoxy group having 1 to 3 substituents independently selected from the substituent group S; １ -C ６ (c14) a substituted (C) alkyl group having 1 to 3 substituents independently selected from the substituent group T; ３ -C ６ ) cycloalkyl group; (c15) (C １ -C ６ ) an alkylsulfanyl group; (c16) (C １ -C ６ ) an alkylsulfinyl group; (c17) (C １ -C ６ ) an alkylsulfonyl group; (c18) (C １ -C ６ (c19) an alkoxycarbonyl group; (c20) a substituted furanyl group having 1 to 3 substituents each independently selected from the substituent group U on the ring; (c21) an oxazolyl group; (c22) a substituted oxazolyl group having 1 to 3 substituents each independently selected from the substituent group U on the ring; (c23) a thienyl group; (c24) a substituted thienyl group having 1 to 3 substituents each independently selected from the substituent group U on the ring; (c25) a thiazolyl group; (c26) a substituted thiazolyl group having 1 to 2 substituents each independently selected from the substituent group U on the ring; (c27) a naphthyl group; (c28) a substituted naphthyl group having 1 to 7 substituents each independently selected from the substituent group U on the ring; (c29) a phenyl group; (c30) (c31) a pyridyl group; (c32) a substituted pyridyl group having 1 to 4 substituents independently selected from the substituent group U on the ring; (c33) a pyridazinyl group; (c34) a substituted pyridazinyl group having 1 to 3 substituents independently selected from the substituent group U on the ring; (c35) a pyrimidinyl group; (c36) a substituted pyrimidinyl group having 1 to 3 substituents independently selected from the substituent group U on the ring; (c37) a pyrazinyl group; (c38) a substituted pyrazinyl group having 1 to 3 substituents independently selected from the substituent group U on the ring; (c39) phenyl (C １ -C ６ ) alkyl group; or (c40) a substituted phenyl (C １ -C ６ ) alkyl group; Y is a nitrogen atom or CR ４ (In the formula, R ４ is a hydrogen atom, a halogen atom or (C １ -C ６ ) represents an alkyl group. ５ａ (d1) a hydrogen atom; (d2) (C １ -C ６ ) alkyl group; or (d3) halo(C １ -C ６ ) represents an alkyl group. ５ｂ (e1) a hydrogen atom; (e2) a halogen atom; (e3) a (C １ -C ６ ) alkyl group; or (e4) halo(C １ -C ６ The substituent group S is: (f1) a cyano group; (f2) a C ３ -C ６ ) cycloalkyl group; (f3) (C １ -C ６ ) an alkoxy group; (f4) (C １ -C ６ ) an alkylsulfanyl group; (f5) (C １ -C ６ ) an alkylsulfinyl group; (f6) (C １ -C ６ ) alkylsulfonyl group; (f7) halo(C ３ -C ６ ) cycloalkyl group; (f8) halo(C １ -C ６ ) alkoxy group; (f9) halo(C １ -C ６ ) alkylsulfanyl group; (f10) halo(C １ -C ６ ) alkylsulfinyl groups; and (f11) halo(C １ -C ６ The substituent group T is composed of: (g1) a cyano group; (g2) (C １ -C ６ ) alkyl group; (g3) (C ３ -C ６ ) cycloalkyl group; (g4) (C １ -C ６ ) an alkoxy group; (g5) (C １ -C ６ ) an alkylsulfanyl group; (g6) (C １ -C ６ ) an alkylsulfinyl group; (g7) (C １ -C ６ ) alkylsulfonyl group; (g8) halo(C １ -C ６ ) alkyl group; (g9) halo(C ３ -C ６ ) cycloalkyl group; (g10) halo(C １ -C ６ ) alkoxy group; (g11) halo(C １ -C ６ ) alkylsulfanyl group; (g12) halo(C １ -C ６ ) alkylsulfinyl group; (g13) halo(C １ -C ６ (g14) an alkylsulfonyl group; and (g15) a phenyl group. The substituent group U consists of (h1) a halogen atom; (h2) a cyano group; (h3) a nitro group; (h4) an amino group; (h5) a hydroxyl group; (h6) a hydroxy (C １ -C ６ ) alkyl group; (h7) (C １ -C ６ ) alkyl group; (h8) (C ２ -C ６ ) alkenyl group; (h9) (C ２ -C ６ ) an alkynyl group; (h10) (C ３ -C ６ ) cycloalkyl group; (h11) halo(C １ -C ６ ) alkyl group; (h12) halo (C ２ -C ６ ) alkenyl group; (h13) halo(C ２ -C ６ ) alkynyl group; (h14) halo(C ３ -C ６ ) cycloalkyl group; (h15) (C １ -C ６ ) an alkoxy group; (h16) (C １ -C ６ ) an alkylsulfanyl group; (h17) (C １ -C ６ ) an alkylsulfinyl group; (h18) (C １ -C ６ ) alkylsulfonyl group; (h19) halo(C １ -C ６ ) alkoxy group; (h20) halo (C １ -C ６ ) alkylsulfanyl group; (h21) halo(C １ -C ６ ) alkylsulfinyl group; (h22) halo(C １ -C ６ ) alkylsulfonyl group; (h23) N-((C １ -C ６ ) alkylcarbonyl) amino group; and (h24) N-((C １ -C ６ ) alkylsulfonyl) amino group. ● represents the bonding site. (i1) an oxazolinyl group; (i2) a substituted oxazolinyl group having 1 to 4 substituents independently selected from the substituent group V on the ring; (i3) an imidazolinyl group; (i4) a substituted imidazolinyl group having 1 to 4 substituents independently selected from the substituent group V on the ring; (i5) an imidazolidinonyl group; (i6) a substituted imidazolidinonyl group having 1 to 4 substituents independently selected from the substituent group V on the ring; (i7) a triazolinonyl group; (i8) a substituted triazolinonyl group having 1 to 2 substituents independently selected from the substituent group V on the ring; (i9) a pyrazolinonyl group; (i10) a substituted pyrazolinonyl group having 1 to 3 substituents independently selected from the substituent group V on the ring; (i11) a pyrazolyl group; (i12) (i13) a triazolyl group; (i14) a substituted triazolyl group having on the ring one to two substituents independently selected from the substituent group V; (i15) a tetrazolyl group; (i16) a substituted tetrazolyl group having on the ring one substituent selected from the substituent group V; (i17) an imidazolyl group; (i18) a substituted imidazolyl group having on the ring one to three substituents independently selected from the substituent group V; (i19) a pyrrolyl group; (i20) a substituted pyrrolyl group having on the ring one to four substituents independently selected from the substituent group V; (i21) a thiazolyl group; (i22) a substituted thiazolyl group having on the ring one to two substituents independently selected from the substituent group V; (i23) an oxazolyl group; (i24) A substituted oxazolyl group having 1 to 2 substituents independently selected from the substituent group V on the ring; (i25) tetrahydrofuranyl (C １ -C ６ (i26) a substituted tetrahydrofuranyl (C １ -C ６ ) alkoxy group; (i27) dioxolanyl (C １ -C ６ (i28) a substituted dioxolanyl (C １ -C ６ ) alkoxy group; (i29) isoxazolinyl (C １ -C ６ (i30) a substituted isoxazolinyl (C １ -C ６ ) alkoxy group; (i31) pyrazolyl (C １ -C ６ (i32) a substituted pyrazolyl (C １ -C ６ ) alkoxy group; (i33) triazolyl (C １ -C ６ (i34) a substituted triazolyl (C １ -C ６ ) alkoxy group; (i35) tetrazolyl (C １ -C ６ (i36) a substituted tetrazolyl (C １ -C ６ ) alkoxy group; (i37) imidazolyl (C １ -C ６ (i38) a substituted imidazolyl (C １ -C ６ ) alkoxy group; (i39) pyrrolyl (C １ -C ６ (i40) a substituted pyrrolyl (C １ -C ６ ) alkoxy group; (i41) thiazolyl (C １ -C ６ (i42) a substituted thiazolyl (C １ -C ６ ) alkoxy group; (i43) oxazolyl (C １ -C ６ ) alkoxy group; or (i44) a substituted oxazolyl (C １ -C ６ The substituent group V is: (j1) a halogen atom; (j2) a cyano group; (j3) (C １ -C ６ ) alkyl group; (j4) (C ２ -C ６ ) alkenyl group; (j5) (C ２ -C ６ ) an alkynyl group; (j6) (C ３ -C ６ ) cycloalkyl group; (j7) halo(C １ -C ６ ) alkyl group; (j8) halo(C ２ -C ６ ) alkenyl group; (j9) halo(C ２ -C ６ ) alkynyl group; (j10) halo(C ３ -C ６ ) cycloalkyl group; (j11) (C １ -C ６ ) an alkoxy group; (j12) (C １ -C ６ ) an alkylsulfanyl group; (j13) (C １ -C ６ ) an alkylsulfinyl group; (j14) (C １ -C ６ ) alkylsulfonyl group; (j15) halo(C １ -C ６ ) alkoxy group; (j16) halo(C １ -C ６ ) alkylsulfanyl group; (j17) halo(C １ -C ６ ) alkylsulfinyl group; (j18) halo(C １ -C ６ ) an alkylsulfonyl group; (j19) (C １ -C ６ ) Alkoxy (C １ -C ６ ) alkyl group; (j20) (C １ -C ６ ) alkylsulfanyl (C １ -C ６ ) alkyl group; (j21) (C １ -C ６ ) an alkoxycarbonyl group; (j22) a phenyl group; (j23) a halogen atom, (C １ -C ６ ) alkyl and halo(C １ -C ６ (j24) a thienyl group; and (j25) a halogen atom, (C １ -C ６ ) alkyl and halo(C １ -C ６ ) a substituted thienyl group having 1 to 3 substituents on the ring independently selected from the group consisting of alkyl, aryl, arylsulfone, arylsulfuric acid ...

2. R １ But, (a1) (C １ -C ６ ) alkyl group; or (a3') N(R ２ａ ) R ２ｂ Group (wherein, R ２ａ and R ２ｂ (b1) a hydrogen atom, (b2) (C １ -C ６ ) alkyl group, (b5) (C ３ -C ６ ) cycloalkyl group, (b6) halo(C １ -C ６ ) alkyl group, (b7) (C １ -C ７ ) an alkylcarbonyl group, or (b8) (C １ -C ６ ) an alkoxycarbonyl group; R ２ａ and R ２ｂ may be the same or different; Het is of formula (Het-1) or formula (Het-2); R ３ (c1) a halogen atom; (c3) (C １ -C ６ ) alkyl group; (c4) (C ２ -C ６ ) alkenyl group; (c6) (C ３ -C ６ ) cycloalkyl group; (c7) (C １ -C ６ ) alkoxy group; (c8) halo(C １ -C ６ (c9) halo(C ２ -C ６ ) alkenyl group; (c11) halo(C ３ -C ６ (c13) a substituted (C) cycloalkyl group having 1 to 3 substituents independently selected from the substituent group S; １ -C ６ (c14) a substituted (C) alkyl group having 1 to 3 substituents independently selected from the substituent group T; ３ -C ６ ) cycloalkyl group; (c15) (C １ -C ６ ) an alkylsulfanyl group; (c16) (C １ -C ６ ) an alkylsulfinyl group; (c17) (C １ -C ６ ) an alkylsulfonyl group; (c18) (C １ -C ６ (c19) an alkoxycarbonyl group; (c20) a substituted furanyl group having 1 to 3 substituents each independently selected from the substituent group U on the ring; (c23) a thienyl group; (c24) a substituted thienyl group having 1 to 3 substituents each independently selected from the substituent group U on the ring; (c25) a thiazolyl group; (c26) a substituted thiazolyl group having 1 to 2 substituents each independently selected from the substituent group U on the ring; (c27) a naphthyl group; (c28) a substituted naphthyl group having 1 to 7 substituents each independently selected from the substituent group U on the ring; (c29) a phenyl group; (c30) a substituted phenyl group having 1 to 5 substituents each independently selected from the substituent group U on the ring; (c31) a pyridyl group; (c32) a substituted pyridyl group having 1 to 4 substituents each independently selected from the substituent group U on the ring; (c39) Phenyl (C １ -C ６ ) alkyl group; or (c40) a substituted phenyl (C １ -C ６ ) alkyl group, Y is a nitrogen atom or CR ４ (In the formula, R ４ represents a hydrogen atom; ５ａ (d1) a hydrogen atom; or (d2) (C １ -C ６ ) alkyl group, R ５ｂ (e1) a hydrogen atom; or (e3) (C １ -C ６ (f1) a cyano group; (f2) (C ３ -C ６ ) cycloalkyl group; (f3) (C １ -C ６ ) an alkoxy group; (f4) (C １ -C ６ ) an alkylsulfanyl group; (f5) (C １ -C ６ ) an alkylsulfinyl group; and (f6) (C １ -C ６ (g1) a cyano group; (g2) (C １ -C ６ ) alkyl group; (g8) halo(C １ -C ６ (h1) a halogen atom; (h2) a cyano group; (h5) a hydroxyl group; (h6) a hydroxy(C １ -C ６ ) alkyl group; (h7) (C １ -C ６ ) alkyl group; (h10) (C ３ -C ６ ) cycloalkyl group; (h11) halo(C １ -C ６ ) alkyl group; (h14) halo(C ３ -C ６ ) cycloalkyl group; (h15) (C １ -C ６ ) an alkoxy group; (h16) (C １ -C ６ ) an alkylsulfanyl group; (h17) (C １ -C ６ ) an alkylsulfinyl group; (h18) (C １ -C ６ ) alkylsulfonyl group; (h19) halo(C １ -C ６ ) alkoxy group; (h20) halo (C １ -C ６ ) alkylsulfanyl group; (h21) halo(C １ -C ６ ) alkylsulfinyl group; (h22) halo(C １ -C ６ ) alkylsulfonyl group; and (h23) N-((C １ -C ６ (i1) an oxazolinyl group; (i2) a substituted oxazolinyl group having 1 to 4 substituents each independently selected from substituent group V on the ring; (i3) an imidazolinyl group; (i4) a substituted imidazolinyl group having 1 to 4 substituents each independently selected from substituent group V on the ring; (i5) an imidazolidinonyl group; (i6) a substituted imidazolidinonyl group having 1 to 4 substituents each independently selected from substituent group V on the ring; (i7) a triazolinonyl group; (i8) a substituted triazolinonyl group having 1 to 2 substituents each independently selected from substituent group V on the ring; (i9) a pyrazolinonyl group; (i10) a substituted pyrazolinonyl group having 1 to 3 substituents each independently selected from substituent group V on the ring; (i11) (i12) a substituted pyrazolyl group having 1 to 3 substituents independently selected from the substituent group V on the ring; (i13) a triazolyl group; (i14) a substituted triazolyl group having 1 to 2 substituents independently selected from the substituent group V on the ring; (i21) a thiazolyl group; (i22) a substituted thiazolyl group having 1 to 2 substituents independently selected from the substituent group V on the ring; (i23) an oxazolyl group; (i24) a substituted oxazolyl group having 1 to 2 substituents independently selected from the substituent group V on the ring; (i25) tetrahydrofuranyl (C １ -C ６ (i26) a substituted tetrahydrofuranyl (C １ -C ６ ) alkoxy group; (i27) dioxolanyl (C １ -C ６ (i28) a substituted dioxolanyl (C １ -C ６ ) alkoxy group; (i29) isoxazolinyl (C １ -C ６ (i30) a substituted isoxazolinyl (C １ -C ６ ) alkoxy group; (i31) pyrazolyl (C １ -C ６ (i32) a substituted pyrazolyl (C １ -C ６ ) alkoxy group; (i33) triazolyl (C １ -C ６ (i34) a substituted triazolyl (C １ -C ６ ) alkoxy group; (i41) thiazolyl (C １ -C ６ (i42) a substituted thiazolyl (C １ -C ６ ) alkoxy group; (i43) oxazolyl (C １ -C ６ ) alkoxy group; or (i44) a substituted oxazolyl (C １ -C ６ ) an alkoxy group, and the substituent group V is: (j1) a halogen atom; (j2) a cyano group; (j3) (C １ -C ６ ) alkyl group; (j4) (C ２ -C ６ ) alkenyl group; (j6) (C ３ -C ６ ) cycloalkyl group; (j7) halo(C １ -C ６ ) alkyl group; (j8) halo(C ２ -C ６ ) alkenyl group; (j10) halo(C ３ -C ６ ) cycloalkyl group; (j11) (C １ -C ６ ) an alkoxy group; (j12) (C １ -C ６ ) an alkylsulfanyl group; (j13) (C １ -C ６ ) an alkylsulfinyl group; (j14) (C １ -C ６ ) alkylsulfonyl group; (j15) halo(C １ -C ６ ) alkoxy group; (j16) halo(C １ -C ６ ) an alkylsulfanyl group; (j20) (C １ -C ６ ) alkylsulfanyl (C １ -C ６ ) alkyl group; (j21) (C １ -C ６ ) an alkoxycarbonyl group; (j22) a phenyl group; (j23) a halogen atom, (C １ -C ６ ) alkyl and halo(C １ -C ６ (j24) a thienyl group; and (j25) a halogen atom, (C １ -C ６ ) alkyl and halo(C １ -C ６ 2. The compound according to claim 1, or a salt thereof, which is a substituted thienyl group having 1 to 3 substituents on the ring, each independently selected from the group consisting of alkyl, aryl, arylsulfonyl ...

3. R １ But, (a1) (C １ -C ６ ) alkyl group; or (a3'') N(R ２ａ ) R ２ｂ Group (wherein, R ２ａ and R ２ｂ (b1) a hydrogen atom, (b2) (C １ -C ６ ) alkyl group, (b7) (C １ -C ７ ) an alkylcarbonyl group, or (b8) (C １ -C ６ ) an alkoxycarbonyl group; R ２ａ and R ２ｂ may be the same or different; Het is of formula (Het-1) or formula (Het-2); R ３ (c1) a halogen atom; (c3) (C １ -C ６ ) alkyl group; (c4) (C ２ -C ６ ) alkenyl group; (c6) (C ３ -C ６ ) cycloalkyl group; (c8) halo(C １ -C ６ (c13) a substituted (C) alkyl group having 1 to 3 substituents independently selected from the substituent group S １ -C ６ (c14) a substituted (C) alkyl group having 1 to 3 substituents independently selected from the substituent group T; ３ -C ６ ) cycloalkyl group; (c18) (C １ -C ６ (c19) a furanyl group; (c23) a thienyl group; (c25) a thiazolyl group; (c26) a substituted thiazolyl group having 1 to 2 substituents independently selected from the substituent group U on the ring; (c27) a naphthyl group; (c29) a phenyl group; (c30) a substituted phenyl group having 1 to 5 substituents independently selected from the substituent group U on the ring; (c31) a pyridyl group; (c32) a substituted pyridyl group having 1 to 4 substituents independently selected from the substituent group U on the ring; or (c40) a substituted phenyl(C １ -C ６ ) alkyl group, Y is a nitrogen atom or CR ４ (In the formula, R ４ represents a hydrogen atom; ５ａ But, (d2) (C １ -C ６ ) alkyl group, R ５ｂ (e1) a hydrogen atom; or (e3) (C １ -C ６ ) alkyl group, and the substituent group S is １ -C ６ (g14) a phenyl group; and (h1) a halogen atom; (h5) a hydroxyl group; (h6) a hydroxy(C １ -C ６ ) alkyl group; (h7) (C １ -C ６ ) alkyl group; (h11) halo(C １ -C ６ ) alkyl group; and (h15) (C １ -C ６ (i10) a substituted pyrazolinonyl group having 1 to 3 substituents independently selected from the substituent group V on the ring; (i11) a pyrazolyl group; (i12) a substituted pyrazolyl group having 1 to 3 substituents independently selected from the substituent group V on the ring; (i13) a triazolyl group; (i14) (i22) a substituted thiazolyl group having 1 to 2 substituents independently selected from the substituent group V on the ring; (i26) a substituted tetrahydrofuranyl group having 1 to 4 substituents independently selected from the substituent group V on the ring (C １ -C ６ (i28) a substituted dioxolanyl (C １ -C ６ (i30) a substituted isoxazolinyl (C １ -C ６ ) alkoxy group; (i31) pyrazolyl (C １ -C ６ (i32) a substituted pyrazolyl (C １ -C ６ (i34) a substituted triazolyl (C １ -C ６ ) alkoxy group; or (i42) a substituted thiazolyl (C １ -C ６ ) an alkoxy group, and the substituent group V is: (j1) a halogen atom; (j3) (C １ -C ６ ) alkyl group; (j4) (C ２ -C ６ ) alkenyl group; (j6) (C ３ -C ６ ) cycloalkyl group; (j7) halo(C １ -C ６ ) alkyl group; (j11) (C １ -C ６ ) an alkoxy group; (j12) (C １ -C ６ ) an alkylsulfanyl group; (j20) (C １ -C ６ ) alkylsulfanyl (C １ -C ６ ) alkyl group; (j21) (C １ -C ６ ) an alkoxycarbonyl group; (j23') a substituted phenyl group having on the ring 1 to 5 substituents independently selected from halogen atoms; and (j24) a thienyl group, or a salt thereof.

4. An agricultural or horticultural herbicide comprising the compound or its salt according to any one of claims 1 to 3 as an active ingredient.

5. A method for using an agricultural and horticultural herbicide, which comprises applying an effective amount of the agricultural and horticultural herbicide according to claim 4 to weeds, soil, paddy fields or cultivation carriers.

6. A method for controlling weeds, which comprises applying an effective amount of the agricultural and horticultural herbicide according to claim 4 to weeds, soil, paddy fields or cultivation carriers.

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