Pyridazine derivative and composition containing same

Abstract

The present invention provides a compound represented by formula (I) [in the formula, R1 represents a phenyl group, etc., R2 represents a C1-C8 chain hydrocarbon group, etc., R3 represents a phenyl group, etc., X1 and X2 are the same or different and represent an oxygen atom, etc., A represents a single bond, etc., Y1 represents OR15, etc., R15 represents a C1-C10 chain hydrocarbon group, etc.] or a salt thereof having an excellent weed control effect.

Description

Pyridazine derivatives and compositions containing the same

[0001] This patent application claims priority under the Paris Convention to and the benefit of Japanese Patent Application No. 2024-110271 (filed July 9, 2024), the entire contents of which are incorporated herein by reference. The present invention relates to pyridazine derivatives and herbicidal compositions containing the same.

[0002] Various compounds have been investigated and put to practical use for the purpose of weed control, and it is known that certain compounds have the effect of inducing male sterility (see, for example, Patent Document 1).

[0003] U.S. Pat. No. 4,345,934

[0004] An object of the present invention is to provide a compound having excellent weed control activity.

[0005] The present inventors have conducted research to find a compound having excellent weed control activity, and as a result have found that a compound represented by the following formula (I) has excellent weed control activity. The present invention is as follows: [1] Formula (I) [In the formula, R 1 is the group G 1 a phenyl group optionally substituted with one or more substituents selected from the group G 1 R represents a 5- or 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from the group consisting of 2 is the group G 2 a C1-C8 chain hydrocarbon group optionally substituted with one or more substituents selected from the group G 3 a C3-C8 alicyclic hydrocarbon group optionally substituted with one or more substituents selected from the group consisting of a halogen atom, a cyano group, OR 10 , C (= Z 1 ) R 11 , C (= Z 1 ) OR 12 , C (= Z 1 ) NR 11 R 12 , mercapto group, S(O) p R13 , or NR 11 R 14 p represents 0, 1, or 2; R 3 is the group G 4 a phenyl group optionally substituted with one or more substituents selected from the group G 4 a 5- or 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from the group G 4 a group represented by formula B1, or a group represented by formula B2 (● represents a bonding site to a nitrogen atom), which may be substituted by one or more substituents selected from the group consisting of: G ７ａ , G ７ｂ and G ７ｃ The combination of ７ａ is C=O or CR ３０ａ R ３１ａ and G ７ｂ is C=O or CR ３０ｂ R ３１ｂ and G ７ｃ is C=O or CR ３０ｃ R ３１ｃ A combination where ７ａ is C=O or CR ３０ａ R ３１ａ and G ７ｂ is C=O or CR ３０ｂ R ３１ｂ and G ７ｃ is NR ３２ｃ , an oxygen atom, a sulfur atom, S═O, or S═O ２ A combination where ７ａ is C=O or CR ３０ａ R ３１ａ and G ７ｂ is NR ３２ｂ , an oxygen atom, a sulfur atom, S═O, or S═O ２ and G ７ｃ is C=O or CR ３０ｃ R ３１ｃ A combination where ７ａ is NR ３２ａ , an oxygen atom, a sulfur atom, S═O, or S═O ２ and G ７ｂ is C=O or CR ３０ｂ R ３１ｂ and G ７ｃis C=O or CR ３０ｃ R ３１ｃ or a combination in which ７ａ is NR ３２ａ , an oxygen atom, a sulfur atom, S═O, or S═O ２ and G ７ｂ is C=O or CR ３０ｂ R ３１ｂ and G ７ｃ is NR ３２ｃ , an oxygen atom, a sulfur atom, S═O, or S═O ２ A combination in which ７ｄ , G ７ｅ , G ７ｆ and G ７ｇ The combination of ７ｄ is C=O or CR ３０ｄ R ３１ｄ and G ７ｅ is C=O or CR ３０ｅ R ３１ｅ and G ７ｆ is C=O or CR ３０ｆ R ３１ｆ and G ７ｇ is C=O or CR ３０ｇ R ３１ｇ A combination where ７ｄ is C=O or CR ３０ｄ R ３１ｄ and G ７ｅ is C=O or CR ３０ｅ R ３１ｅ and G ７ｆ is C=O or CR ３０ｆ R ３１ｆ and G ７ｇ is NR ３２ｇ , an oxygen atom, a sulfur atom, S═O, or S═O ２ A combination where ７ｄ is C=O or CR ３０ｄ R ３１ｄ and G ７ｅ is C=O or CR ３０ｅ R ３１ｅ and G ７ｆ is NR ３２ｆ , an oxygen atom, a sulfur atom, S═O, or S═O ２ and G ７ｇ is C=O or CR ３０ｇ R ３１ｇ A combination where７ｄ is C=O or CR ３０ｄ R ３１ｄ and G ７ｅ is NR ３２ｅ , an oxygen atom, a sulfur atom, S═O, or S═O ２ and G ７ｆ is C=O or CR ３０ｆ R ３１ｆ and G ７ｇ is C=O or CR ３０ｇ R ３１ｇ A combination where ７ｄ is C=O or CR ３０ｄ R ３１ｄ and G ７ｅ is NR ３２ｅ , an oxygen atom, a sulfur atom, S═O, or S═O ２ and G ７ｆ is C=O or CR ３０ｆ R ３１ｆ and G ７ｇ is NR ３２ｇ , an oxygen atom, a sulfur atom, S═O, or S═O ２ A combination where ７ｄ is NR ３２ｄ , an oxygen atom, a sulfur atom, S═O, or S═O ２ and G ７ｅ is C=O or CR ３０ｅ R ３１ｅ and G ７ｆ is C=O or CR ３０ｆ R ３１ｆ and G ７ｇ is C=O or CR ３０ｇ R ３１ｇ A combination where ７ｄ is NR ３２ｄ , an oxygen atom, a sulfur atom, S═O, or S═O ２ and G ７ｅ is C=O or CR ３０ｅ R ３１ｅ and G ７ｆ is C=O or CR ３０ｆ R ３１ｆ and G ７ｇ is NR ３２ｇ , an oxygen atom, a sulfur atom, S═O, or S═O ２ or a combination in which ７ｄ is NR ３２ｄ, an oxygen atom, a sulfur atom, S═O, or S═O ２ and G ７ｅ is C=O or CR ３０ｅ R ３１ｅ and G ７ｆ is NR ３２ｆ , an oxygen atom, a sulfur atom, S═O, or S═O ２ and G ７ｇ is C=O or CR ３０ｇ R ３１ｇ A combination where X 1 and X 2 are the same or different and represent an oxygen atom or a sulfur atom; Y 1 is OR 15 or SR 15 m and n are the same or different and represent 0, 1, or 2; A is a single bond, an oxygen atom, a sulfur atom, —S(O)—, —S(O)2—, or —CR 4 R 5 -, -C (=Z 4 ) - or -NR 6 represents -, R 4 and R 5 are the same or different and represent a C1-C3 alkyl group optionally substituted with one or more halogen atoms, a C1-C3 alkoxy group optionally substituted with one or more halogen atoms, a hydroxy group, or a hydrogen atom, or 4 and R 5 and together form a C2-C5 alkylene group, or —O(CH2) q O—, q represents 2, 3 or 4, Z 4 represents an oxygen atom, a sulfur atom, or CH; R 6 represents a C1-C3 alkyl group optionally substituted with one or more halogen atoms, C(=Z 5 ) R 34 Group, C (=Z 5 ) OR 34 group or a hydrogen atom; Z 1 , Z 2 , Z 3 , and Z 5 are the same or different and represent an oxygen atom or a sulfur atom; R 10represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, a C3-C6 alicyclic hydrocarbon group optionally substituted with one or more halogen atoms, or a group G 6 R represents a phenyl group which may be substituted with one or more substituents selected from the group consisting of 11 , R 21 , and R 26 are the same or different and represent a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, a C3-C6 alicyclic hydrocarbon group optionally substituted with one or more halogen atoms, a group G 6 R represents a phenyl group optionally substituted with one or more substituents selected from the group consisting of 12 , R 20 , R 22 , R 25 , and R 27 are the same or different and represent a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, a C3-C6 alicyclic hydrocarbon group optionally substituted with one or more halogen atoms, or a hydrogen atom; R 13 , R 23 , and R 28 are the same or different and represent a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, a C3-C6 alicyclic hydrocarbon group optionally substituted with one or more halogen atoms, or a group G 6 R represents a phenyl group which may be substituted with one or more substituents selected from the group consisting of 14 , R 24 , R 29 , and R 34 are the same or different and represent a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, or a C3-C6 alicyclic hydrocarbon group optionally substituted with one or more halogen atoms, R ３５ and R ３６ together with the nitrogen atom to which they are bonded, represent a saturated or unsaturated 5- or 6-membered cyclic amino group {the cyclic amino group may be substituted with one or more substituents selected from the group consisting of a C1-C3 alkyl group optionally substituted with one or more halogen atoms, and a halogen atom}, R 15 is the group G ８a C1-C10 chain hydrocarbon group optionally substituted with one or more substituents selected from the group consisting of a C3-C6 alicyclic hydrocarbon group optionally substituted with one or more halogen atoms, a benzyl group {the phenyl moiety in the benzyl group is selected from the group G 6 and the methylene portion may be substituted with one or two C1-C3 alkyl groups}, or a hydrogen atom; R ３０ａ 、 R ３０b 、 R ３０c , R ３０d 、 R ３０e 、 R ３０f 、 R ３０g 、 R ３１ａ , R ３１b 、 R ３１c , R ３１d 、 R ３１e 、 R ３１f 、 and R ３１g are the same or different and represent a C1-C6 alkyl group optionally substituted with one or more halogen atoms, a halogen atom, or a hydrogen atom; R ３２ａ 、 R ３２b 、 R ３２c , R ３２d 、 R ３２e 、 R ３２f 、 and R ３２g are the same or different and represent a C1-C6 alkyl group optionally substituted with one or more halogen atoms, a (C1-C3 alkyl)carbonyl group optionally substituted with one or more halogen atoms, or a hydrogen atom; R ３３ａ 、 R ３３b 、 R ３３c , R ３３d 、 R ３３e 、 and R ３３fare the same or different and represent a C1-C3 alkyl group optionally substituted with one or more halogen atoms, a halogen atom, or a hydrogen atom. 1 : a C1-C3 alkyl group optionally substituted with one or more halogen atoms, group G １－１ a C3-C6 cycloalkyl group optionally substituted by one or more substituents selected from the group consisting of: OR 20 Group, C (=Z 2 ) R 21 Group, C (=Z 2 ) OR 22 Group, C (=Z 2 ) NR 21 R 22 group, mercapto group, S(O) n R 23 group, NR 20 R 24 Group G consisting of a nitro group, a halogen atom, and a cyano group. 1-1 Group G: a group consisting of a halogen atom and a cyano group. 2 Group G: a group consisting of a C1-C3 alkoxy group optionally substituted with one or more halogen atoms, a C1-C3 alkylthio group optionally substituted with one or more halogen atoms, a C1-C3 alkylsulfinyl group optionally substituted with one or more halogen atoms, a C1-C3 alkylsulfonyl group optionally substituted with one or more halogen atoms, a halogen atom, a cyano group, a hydroxy group, and a mercapto group. 3 Group G: a group consisting of a C1-C3 alkyl group optionally substituted with one or more halogen atoms, a C1-C3 alkoxy group optionally substituted with one or more halogen atoms, a C1-C3 alkylthio group optionally substituted with one or more halogen atoms, a C1-C3 alkylsulfinyl group optionally substituted with one or more halogen atoms, a C1-C3 alkylsulfonyl group optionally substituted with one or more halogen atoms, an oxo group, a thioxo group, a halogen atom, a cyano group, a hydroxy group, and a mercapto group. 4 :Group G ４－2 a C1-C6 alkyl group optionally substituted with one or more substituents selected from the group G ４－１ a C3-C6 cycloalkyl group optionally substituted by one or more substituents selected from the group consisting of: OR 25Group, C (=Z 3 ) R 26 Group, C (=Z 3 ) OR 27 Group, C (=Z 3 ) NR 26 R 27 group, mercapto group, S(O) m R 28 group, NR 25 R 29 group, NR ３５ R ３６ group, nitro group, halogen atom, SF ５ Group G consisting of a cyano group, a morpholino group, and a cyano group. 6 Group G: a group consisting of a C1-C3 alkoxy group optionally substituted with one or more halogen atoms, a C1-C3 alkylthio group optionally substituted with one or more halogen atoms, a C1-C3 alkylsulfinyl group optionally substituted with one or more halogen atoms, a C1-C3 alkylsulfonyl group optionally substituted with one or more halogen atoms, a halogen atom, a cyano group, a nitro group, a hydroxy group, and a mercapto group. ４－１ C1-C6 chain hydrocarbon group, C1-C6 alkoxy group, C1-C6 alkylthio group, C1-C6 alkylamino group, C2-C8 dialkylamino group, (C1-C6 alkyl)carbonyl group, (C1-C6 alkoxy)carbonyl group, (C1-C6 alkylamino)carbonyl group, (C2-C8 dialkylamino)carbonyl group, C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, (C1-C6 alkylamino)sulfonyl group, (C2-C8 dialkylamino)sulfonyl group {the C1-C6 chain hydrocarbon group The hydrogen hydride group, the C1-C6 alkoxy group, the C1-C6 alkylthio group, the C1-C6 alkylamino group, the C2-C8 dialkylamino group, the (C1-C6 alkyl)carbonyl group, the (C1-C6 alkoxy)carbonyl group, the (C1-C6 alkylamino)carbonyl group, the (C2-C8 dialkylamino)carbonyl group, the C1-C6 alkylsulfinyl group, the C1-C6 alkylsulfonyl group, the (C1-C6 alkylamino)sulfonyl group, and the (C2-C8 dialkylamino)sulfonyl group are each selected from the group G 4-1-1and optionally substituted with one or more substituents selected from the group consisting of a halogen atom, a cyano group, a nitro group, a hydroxy group, an amino group, a formyl group, an aminocarbonyl group, an aminosulfonyl group, and SF ５ Group G 4-1-1 Group G: a group consisting of halogen atoms, cyano groups, nitro groups, hydroxy groups, amino groups, oxo groups, thioxo groups, aminocarbonyl groups, aminosulfonyl groups, C3-C6 cycloalkyl groups, C1-C3 alkoxy groups, C1-C3 alkylthio groups, (C1-C3 alkyl)carbonyl groups, (C1-C3 alkoxy)carbonyl groups, C1-C3 alkylsulfinyl groups, and C1-C3 alkylsulfonyl groups (the C3-C6 cycloalkyl groups, the C1-C3 alkoxy groups, the C1-C3 alkylthio groups, the (C1-C3 alkoxy)carbonyl groups, the C1-C3 alkylsulfinyl groups, and the C1-C3 alkylsulfonyl groups are optionally substituted with one or more halogen atoms). ４－２ a C1-C6 alkoxy group, a C1-C6 alkylthio group, a C1-C6 alkylamino group, a C2-C8 dialkylamino group, a (C1-C6 alkyl)carbonyl group, a (C1-C6 alkoxy)carbonyl group, a (C1-C6 alkylamino)carbonyl group, a (C2-C8 dialkylamino)carbonyl group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group, a (C1-C6 alkylamino)sulfonyl group, a (C2-C8 dialkylamino)sulfonyl group {said C1-C6 alkoxy group, a C1-C6 alkylthio group, a C1-C6 alkylamino group, a C2-C8 dialkylamino group, a (C1-C6 alkyl)carbonyl group, a (C1-C6 alkoxy)carbonyl group, a (C1-C6 alkylamino)carbonyl group, a (C2-C8 dialkylamino)carbonyl group {said C1-C6 alkoxy group, a C1-C6 alkylthio group, a C1-C6 alkylamino group, a C2-C8 dialkylamino group, a (C1-C6 alkyl)carbonyl group, a (C1-C6 alkylamino)sulfonyl group, a (C2-C8 dialkylamino)sulfonyl group {said C1-C6 alkoxy group, a C1-C6 alkylthio ... The alkoxy group, the C1-C6 alkylthio group, the C1-C6 alkylamino group, the C2-C8 dialkylamino group, the (C1-C6 alkyl)carbonyl group, the (C1-C6 alkoxy)carbonyl group, the (C1-C6 alkylamino)carbonyl group, the (C2-C8 dialkylamino)carbonyl group, the C1-C6 alkylsulfinyl group, the C1-C6 alkylsulfonyl group, the (C1-C6 alkylamino)sulfonyl group, and the (C2-C8 dialkylamino)sulfonyl group are each selected from the group G 4-1-1 and optionally substituted with one or more substituents selected from the group consisting of a halogen atom, a cyano group, a nitro group, a hydroxy group, an amino group, a formyl group, an aminocarbonyl group, an aminosulfonyl group, and SF ５ Group G８ a group consisting of a (C1-C6 alkyl)carbonyl group optionally substituted with one or more halogen atoms, a (C1-C6 alkoxy)carbonyl group optionally substituted with one or more halogen atoms, a C1-C6 alkoxy group optionally substituted with one or more halogen atoms, a C1-C6 alkylthio group optionally substituted with one or more halogen atoms, a cyano group, and a halogen atom.] (hereinafter referred to as Compound N of the Present Invention) or a salt thereof (hereinafter the compound represented by Formula (I) or a salt thereof will be referred to as Compound of the Present Invention). [2] R 3 But the group G 4 a phenyl group optionally substituted with one or more substituents selected from the group G 4 R is a 5- or 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from 15 a C1-C10 chain hydrocarbon group optionally substituted with one or more halogen atoms, a C3-C6 alicyclic hydrocarbon group optionally substituted with one or more halogen atoms, a benzyl group {the phenyl moiety in the benzyl group is selected from the group G 6 and the methylene moiety may be substituted with one or two C1-C3 alkyl groups}, or a hydrogen atom; 1 is a C1-C3 alkyl group optionally substituted with one or more halogen atoms, a C3-C6 cycloalkyl group, OR 20 Group, C (=Z 2 ) R 21 Group, C (=Z 2 ) OR 22 Group, C (=Z 2 ) NR 21 R 22 group, mercapto group, S(O) n R 23 group, NR 20 R 24 group, a nitro group, a halogen atom, and a cyano group; 4 is a C1-C3 alkyl group optionally substituted with one or more halogen atoms, a C3-C6 cycloalkyl group, OR 25 Group, C (=Z 3 ) R 26 Group, C (=Z 3 ) OR27 Group, C (=Z 3 ) NR 26 R 27 group, mercapto group, S(O) m R 28 group, NR 25 R 29 [3] The compound or salt thereof according to [1], wherein X is the group consisting of a nitro group, a halogen atom, and a cyano group. 1 and X 2 [4] The compound or salt thereof according to [1] or [2], wherein Y is an oxygen atom. 1 is OR 15 [5] The compound or salt thereof according to any one of [1] to [3], wherein R is a group. 2 [6] The compound or salt thereof according to any one of [1] to [4], wherein R is a C1-C3 alkyl group optionally substituted with one or more halogen atoms, or a C3-C6 cycloalkyl group optionally substituted with one or more halogen atoms. 1 But the group G 1 [7] The compound or salt thereof according to any one of [1] to [5], wherein R is a phenyl group optionally substituted with one or more substituents selected from the following: １ But the group G 1 In the 5-6 membered aromatic heterocyclic group, the atom bonded to A is a carbon atom, and A is an oxygen atom or -CR 4 R 5 [8] The compound or salt thereof according to any one of [1] to [5], wherein R １ But the group G 1 In the 5-membered aromatic heterocyclic group, the atom bonding to A is a nitrogen atom, and A is -CR 4 R 5 [9] The compound or salt thereof according to any one of [1] to [5], wherein R １ But the group G １

[10] The compound or salt thereof according to any one of [1] to [5], wherein A is a 5- or 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from the group consisting of:１ is the group consisting of a C1-C3 alkyl group optionally substituted with one or more halogen atoms, a C1-C3 alkoxy group optionally substituted with one or more halogen atoms, a C1-C3 alkylthio group optionally substituted with one or more halogen atoms, a C3-C6 cycloalkyl group, a halogen atom, a nitro group, and a cyano group.

[11] A compound or a salt thereof according to any one of [1] to [7] or

[10] , wherein A is -CH2-.

[12] A compound or a salt thereof according to any one of [1] to [6] or

[10] , wherein A is a single bond.

[13] A compound or a salt thereof according to any one of [1] to [7] or

[10] , wherein A is an oxygen atom.

[14] R 3 But the group G 4 a phenyl group optionally substituted with 1 to 3 substituents selected from the group G 4

[15] The compound or salt thereof according to any one of [1] to

[13] , wherein R is a 5- or 6-membered aromatic heterocyclic group optionally substituted with 1 to 3 substituents selected from the following: ３ But the group G ４

[16] The compound or salt thereof according to any one of [1] to

[14] , wherein R is a phenyl group optionally substituted with 1 to 3 substituents selected from the following: ３ But the group G ４

[17] The compound or salt thereof according to any one of [1] to

[14] , wherein R is a 5- or 6-membered aromatic heterocyclic group optionally substituted with 1 to 3 substituents selected from the following: ３ But the group G ４

[18] The compound or salt thereof according to any one of [1] to

[14] or

[16] , wherein R is a 5-membered aromatic heterocyclic group optionally substituted with 1 to 3 substituents selected from the following: ３ is a 5-membered aromatic heterocyclic group represented by formula D-1 or D-2 [wherein ● represents a bonding site with a nitrogen atom, G １０ａ , G １０ｂ , G １０ｃ , G １０ｄ , G １０ｅ , and G １０ｆ are the same or different and represent a nitrogen atom or a group G ４R represents a methine group optionally substituted with a substituent selected from the group consisting of ３７ａ , and R ３７ｂ are the same or different and represent a C1-C3 alkyl group optionally substituted with one or more halogen atoms, a C3-C6 cycloalkyl group optionally substituted with one or more halogen atoms, or a hydrogen atom.]

[19] The compound or salt thereof according to any one of [1] to

[14] ,

[16] , or

[17] , wherein R ３ But the group G ４

[20] The compound or salt thereof according to any one of [1] to

[14] or

[16] , wherein R is a 6-membered aromatic heterocyclic group optionally substituted with 1 to 3 substituents selected from the following: ３ But the group G ４

[21] The compound or salt thereof according to any one of [1] to

[14] ,

[16] , or

[19] , wherein R is a pyridyl group optionally substituted with 1 to 3 substituents selected from the following: ３ is a group represented by formula B1-1 or a group represented by formula B2-1 [wherein ● represents a bonding site with a nitrogen atom, R ３３ａ 、 R ３３b 、 R ３３c , R ３３d 、 R ３３e 、 and R ３３f are the same or different and represent a C1-C3 alkyl group optionally substituted with one or more halogen atoms, a halogen atom, or a hydrogen atom; G ７ａ1 , G ７ｃ1 , G ７ｄ1 , and G ７g1 are the same or different and represent an oxygen atom or a sulfur atom; G ７b1 , G ７e1 , and G ７f1 represents a methylene group {the methylene group may be substituted with one or more substituents selected from the group consisting of a C1-C3 alkyl group optionally substituted with one or more halogen atoms, and a halogen atom}.].

[22] The compound or salt thereof according to any one of [1], [3] to

[13] , wherein R ３ is a group represented by formula B1-2 [wherein ● represents a bonding site with a nitrogen atom, G ７ａ2 , and G ７ｃ2 are the same or different and represent an oxygen atom or a sulfur atom; ７b2 represents a methylene group {the methylene group may be substituted with one or more substituents selected from the group consisting of a C1-C3 alkyl group optionally substituted with one or more halogen atoms, and a halogen atom}.].

[23] The compound or salt thereof according to any one of [1], [3] to

[13] , or

[21] , ４ is the group consisting of a C1-C3 alkyl group optionally substituted with one or more halogen atoms, a C1-C3 alkoxy group optionally substituted with one or more halogen atoms, a C1-C3 alkylthio group optionally substituted with one or more halogen atoms, a C1-C3 alkylsulfinyl group optionally substituted with one or more halogen atoms, a C1-C3 alkylsulfonyl group optionally substituted with one or more halogen atoms, a C3-C6 cycloalkyl group optionally substituted with one or more halogen atoms, a C3-C6 cycloalkyl group optionally substituted with a cyano group, a halogen atom, a nitro group, and a cyano group.

[24] A herbicidal composition comprising the compound or salt thereof according to any one of [1] to

[23] and an inert carrier.

[25] A method for controlling weeds, comprising the step of applying the compound or salt thereof according to any one of [1] to

[23] to weeds or soil in which weeds grow.

[23] Use of the compound according to any one of [1] to

[23] or a salt thereof for controlling weeds.

[27] A composition comprising one or more components selected from the group consisting of Group (d) and Group (f), and the compound according to any one of [1] to

[23] or a salt thereof: Group (d): a phytotoxicity-reducing component; Group (f): a herbicidal active component.

[0006] The present invention makes it possible to control weeds.

[0007] The substituents of the present invention will be explained. A halogen atom refers to a fluorine atom, chlorine atom, bromine atom, or iodine atom. When a substituent is substituted with two or more halogen atoms or substituents, these halogen atoms or substituents may be the same or different. In this specification, the expression "optionally substituted with one or more substituents selected from group X" means that when two or more substituents selected from group X are present, these substituents may be the same or different. In this specification, the expression "CX-CY" means that the number of carbon atoms is X to Y. For example, the expression "C1-C8" means that the number of carbon atoms is 1 to 8. The chain hydrocarbon group represents an alkyl group, an alkenyl group, or an alkynyl group. Examples of alkyl groups include a methyl group, an ethyl group, a propyl group, an isopropyl group, a 1,1-dimethylpropyl group, a 1,2-dimethylpropyl group, a 1-ethylpropyl group, a butyl group, a sec-butyl group, a tert-butyl group, a pentyl group, a hexyl group, and an octyl group. Examples of alkenyl groups include vinyl, 1-propenyl, 2-propenyl, 1-methyl-1-propenyl, 1-methyl-2-propenyl, 1,2-dimethyl-1-propenyl, 1-ethyl-2-propenyl, 3-butenyl, 4-pentenyl, 5-hexenyl, and 7-octenyl. Examples of alkynyl groups include ethynyl, 1-propynyl, 2-propynyl, 1-methyl-2-propynyl, 1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 2-butynyl, 4-pentynyl, 5-hexynyl, and 7-octynyl. Examples of alkoxy groups include methoxy, ethoxy, propoxy, isopropoxy, butoxy, tert-butoxy, pentyloxy, hexyloxy, and octyloxy groups. Examples of haloalkoxy groups include trifluoromethoxy, difluoromethoxy, trifluoroethoxy, pentafluoroethoxy, and chlorodifluoromethoxy groups.Examples of alkylsulfinyl groups include methylsulfinyl groups, ethylsulfinyl groups, propylsulfinyl groups, and isopropylsulfinyl groups. Examples of alkylsulfonyl groups include methylsulfonyl groups, ethylsulfonyl groups, propylsulfonyl groups, and isopropylsulfonyl groups.

[0008] Alicyclic hydrocarbon groups include, for example, cycloalkyl groups and cycloalkenyl groups. Cycloalkyl groups include, for example, cyclopropyl groups, cyclobutyl groups, cyclopentyl groups, cyclohexyl groups, and cyclooctyl groups. Cycloalkenyl groups include, for example, cyclopentenyl groups, cyclohexenyl groups, and cyclooctenyl groups.

[0009] Examples of the 5- to 6-membered aromatic heterocyclic group include a pyrrolyl group, a furyl group, a thienyl group, a pyrazolyl group, an imidazolyl group, a triazolyl group, a tetrazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, an oxadiazolyl group, a thiadiazolyl group, a pyridyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, a triazinyl group, and a tetrazinyl group.

[0010] Examples of the 8- to 10-membered fused aromatic heterocyclic group include a quinolyl group, a benzoxazolyl group, a benzothiazolyl group, a benzimidazolyl group, an indazolyl group, a benzisothiazolyl group, and a benzothiophenyl group. Examples of the saturated or unsaturated 5- to 6-membered cyclic amino group include a pyrrolidinyl group, a piperidinyl group, and a pyrrolyl group.

[0011] The compound of the present invention may exist in one or more stereoisomers. Examples of stereoisomers include enantiomers, diastereomers, atropisomers, and geometric isomers. The compound of the present invention includes each stereoisomer and a mixture of stereoisomers in any ratio.

[0012] The compound of the present invention may form a base addition salt such as an isopropylamine salt, a dimethylamine salt, a sodium salt, a potassium salt, etc., when mixed with a base such as isopropylamine, dimethylamine, sodium carbonate, potassium carbonate, etc. The compound of the present invention may form an acid addition salt such as a hydrochloride, a sulfate, a nitrate, a phosphate, an acetate, a benzoate, etc., when mixed with an acid such as hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, acetic acid, benzoic acid, etc.

[0013] The compound of the present invention may exist as a zwitterion. In addition, the compound of the present invention may have an N-oxide structure in which at least one nitrogen atom contained in the compound of formula (I) is oxidized to form a bond with an oxygen atom.

[0014] The following compounds are examples of the compound N of the present invention.

[0015] [Embodiment 1] In the compound N of the present invention, X 1 is an oxygen atom. [Embodiment 2] In the compound N of the present invention, Y 1 But OR 15 [Embodiment 3] In the compound N of the present invention, X 1 is an oxygen atom, and Y 1 But OR 15 [Embodiment 4] In the compound N of the present invention, X 1 is an oxygen atom, and Y 1 But OR 15 and R 15 is a hydrogen atom. [Embodiment 5] In the compound N of the present invention, X 1 is an oxygen atom, and Y 1 But OR 15 and R 15 is a C1-C10 chain hydrocarbon group. [Embodiment 6] In the compound N of the present invention, X 1 is an oxygen atom, and Y 1 But OR 15 and R 15 is a C3-C6 alicyclic hydrocarbon group. [Embodiment 7] In the compound N of the present invention, X 1 is an oxygen atom, and Y 1 But OR 15 and R15 benzyl group {the phenyl moiety in the benzyl group is a group G 6 and the methylene moiety may be substituted with one or two C1-C3 alkyl groups. 1 is an oxygen atom, and Y １ But OR 15 is a group, and R 15 A compound in which the X group is a benzyl group. 1 is an oxygen atom, and Y 1 But OR 15 and R 15 is a C1-C4 alkyl group or a hydrogen atom. 2 is an oxygen atom. [Aspect 11] A compound according to aspect 1, 2 is an oxygen atom. [Aspect 12] A compound according to aspect 2, wherein X 2 is an oxygen atom. [Aspect 13] A compound according to aspect 3, 2 is an oxygen atom. [Aspect 14] A compound according to aspect 4, wherein X 2 is an oxygen atom. [Aspect 15] A compound according to aspect 5, wherein X 2 is an oxygen atom. [Aspect 16] A compound according to aspect 6, wherein X 2 is an oxygen atom. [Aspect 17] A compound according to aspect 7, wherein X 2 is an oxygen atom. [Aspect 18] A compound according to aspect 8, wherein X 2 is an oxygen atom. [Aspect 19] In aspect 9, X 2 is an oxygen atom. [Embodiment 20] In the compound N of the present invention, R 2 But the group G 2 a C1-C4 chain hydrocarbon group optionally substituted with one or more substituents selected from group G 3 a C3-C6 alicyclic hydrocarbon group optionally substituted with one or more substituents selected from the group consisting of a halogen atom, a cyano group, OR 10 , C (= Z 1 ) R 11 , C (= Z 1 ) OR 12, C (= Z 1 ) NR 11 R 12 , S(O) p R 13 group, or NR 10 R 14 [Embodiment 21] In the compound N of the present invention, R 2 But the group G 2 a C1-C4 alkyl group optionally substituted with one or more substituents selected from the group G 3 a C3-C6 cycloalkyl group optionally substituted with one or more substituents selected from the group consisting of a halogen atom, a cyano group, OR 10 , or S(O) p R 13 [Embodiment 22] In the compound N of the present invention, R 2 But the group G 2 a C1-C4 alkyl group optionally substituted with one or more substituents selected from the group consisting of OR 10 group, or S(O) p R 13 and R 10 is a C1-C3 alkyl group optionally substituted with one or more halogen atoms, and R 13 is a C1-C3 alkyl group optionally substituted with one or more halogen atoms. 2 But the group G 2 [Embodiment 24] In the compound N of the present invention, R 2 is a C1-C4 alkyl group. 2 is an isopropyl group. [Embodiment 26] In the compound N of the present invention, R 2 is an ethyl group. [Embodiment 27] In the compound N of the present invention, R 2 is a methyl group. [Embodiment 28] In the compound N of the present invention, R 2 is a C1-C4 alkyl group. 2 is a methyl group. 2is a C1-C4 alkyl group. 2 is a methyl group. 2 is a C1-C4 alkyl group. 2 is a methyl group. 2 is a C1-C4 alkyl group. 2 is a methyl group. 2 is a C1-C4 alkyl group. 2 is a methyl group. 2 is a C1-C4 alkyl group. 2 is a methyl group. 2 is a C1-C4 alkyl group. 2 is a methyl group. 2 is a C1-C4 alkyl group. 2 is a methyl group. 2 is a C1-C4 alkyl group. 2 is a methyl group. 2 is a C1-C4 alkyl group. 2 is a methyl group. 2 is a C1-C4 alkyl group. 2 is a methyl group. 2 is a C1-C4 alkyl group. 2 is a methyl group. 2is a C1-C4 alkyl group. 2 is a methyl group. 2 is a C1-C4 alkyl group. 2 is a methyl group. 2 is a C1-C4 alkyl group. 2 is a methyl group. 2 is a C1-C4 alkyl group. 2 is a methyl group. 2 is a C1-C4 alkyl group. 2 is a methyl group. 2 is a C1-C4 alkyl group. 2 is a methyl group. 2 is a C1-C4 alkyl group. 2 is a methyl group. 2 is a C1-C4 alkyl group. 2 is a methyl group. [Embodiment 68] In the compound N of the present invention, R 1 But the group G 1 [Embodiment 69] In the compound N of the present invention, R 1 But the group G 1 [Embodiment 70] In the compound N of the present invention, R 1 But the group G 11 Group G: Compounds each of which is a phenyl group optionally substituted with one or more substituents selected from the following: 11: nitro group, halogen atom, cyano group, methyl group, ethyl group, isopropyl group, group G 1-1 The group consisting of a cyclopropyl group, a trifluoromethyl group, a difluoromethyl group, a trifluoromethoxy group, a difluoromethoxy group, a trifluoromethylthio group, a trifluoromethylsulfinyl group, a trifluoromethylsulfonyl group, a methylthio group, a methylsulfinyl group, a methylsulfonyl group, a difluoromethylthio group, a difluoromethylsulfinyl group, and a difluoromethylsulfonyl group, each of which may be substituted by one or more substituents selected from the group consisting of a cyclopropyl group, a trifluoromethyl group, a difluoromethylsulfonyl group, a trifluoromethylthio group, a difluoromethylsulfinyl group, and a difluoromethylsulfonyl group. 1 But the group G 11 A compound of the present invention, wherein A is a single bond, an oxygen atom, a sulfur atom, —CH—, or —NR 6 - and R 6 is a C1-C3 alkyl group or a hydrogen atom. [Embodiment 73] In compound N of the present invention, A is a single bond, —CH—, or —NR 6 - and R 6 is a C1-C3 alkyl group or a hydrogen atom. [Aspect 74] A compound of the present invention, in which A is a single bond or -CH2-. [Aspect 75] A compound of the present invention, in which A is a single bond. [Aspect 76] A compound of the present invention, in which A is -CH2-. [Aspect 77] A compound of the present invention, in which R 1 But the group G 11 A is a single bond, —CH—, or NR 6 and R 6 is a C1-C3 alkyl group or a hydrogen atom. 1 But the group G 11 A compound in which A is a phenyl group optionally substituted with one or more substituents selected from the group consisting of: 1 But the group G 11A compound in which A is a phenyl group optionally substituted with one or more substituents selected from the group consisting of: 1 But the group G 11 A compound in which R is a 5- or 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from the group consisting of: 1 But the group G 11 A is a single bond, —CH—, or —NR 6 - and R 6 is a C1-C3 alkyl group or a hydrogen atom. 1 But the group G 11 A compound in which A is a phenyl group optionally substituted with one or more substituents selected from the group consisting of: 1 But the group G 11 A compound in which A is a phenyl group optionally substituted with one or more substituents selected from the group consisting of: 1 But the group G 11 A compound in which R is a 5- or 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from the group consisting of: 1 But the group G 11 A is a single bond, —CH—, or —NR 6 - and R 6 is a C1-C3 alkyl group or a hydrogen atom. 1 But the group G 11 A compound in which A is a phenyl group optionally substituted with one or more substituents selected from the group consisting of: 1 But the group G 11 A compound in which A is a phenyl group optionally substituted with one or more substituents selected from the group consisting of: 1 But the group G 11A compound in which R is a 5- or 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from the group consisting of: 1 But the group G 11 A is a single bond, —CH—, or —NR 6 - and R 6 is a C1-C3 alkyl group or a hydrogen atom. 1 But the group G 11 A compound in which A is a phenyl group optionally substituted with one or more substituents selected from the group consisting of: 1 But the group G 11 A compound in which A is a phenyl group optionally substituted with one or more substituents selected from the group consisting of: 1 But the group G 11 A compound in which R is a 5- or 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from the group consisting of: 1 But the group G 11 A is a single bond, —CH—, or —NR 6 - and R 6 is a C1-C3 alkyl group or a hydrogen atom. 1 But the group G 11 A compound in which A is a phenyl group optionally substituted with one or more substituents selected from the group consisting of: 1 But the group G 11 A compound in which A is a phenyl group optionally substituted with one or more substituents selected from the group consisting of: 1 But the group G 11 A compound in which R is a 5- or 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from the group consisting of: 1 But the group G 11A is a single bond, —CH—, or —NR 6 - and R 6 is a C1-C3 alkyl group or a hydrogen atom. 1 But the group G 11 A compound in which A is a phenyl group optionally substituted with one or more substituents selected from the group consisting of: 1 But the group G 11 A compound in which A is a phenyl group optionally substituted with one or more substituents selected from the group consisting of: 1 But the group G 11 A compound in which R is a 5- or 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from the group consisting of: 1 But the group G 11 A is a single bond, —CH—, or —NR 6 - and R 6 is a C1-C3 alkyl group or a hydrogen atom. 1 But the group G 11 A compound in which A is a phenyl group optionally substituted with one or more substituents selected from the group consisting of: 1 But the group G 11 A compound in which A is a phenyl group optionally substituted with one or more substituents selected from the group consisting of: 1 But the group G 11 A compound in which R is a 5- or 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from the group consisting of: 1 But the group G 11 A is a single bond, —CH—, or —NR 6 - and R 6is a C1-C3 alkyl group or a hydrogen atom. 1 But the group G 11 A compound in which A is a phenyl group optionally substituted with one or more substituents selected from the group consisting of: 1 But the group G 11 A compound in which A is a phenyl group optionally substituted with one or more substituents selected from the group consisting of: 1 But the group G 11 A compound in which R is a 5- or 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from the group consisting of: 1 But the group G 11 A is a single bond, —CH—, or —NR 6 - and R 6 is a C1-C3 alkyl group or a hydrogen atom. 1 But the group G 11 A compound in which A is a phenyl group optionally substituted with one or more substituents selected from the group consisting of: 1 But the group G 11 A compound in which A is a phenyl group optionally substituted with one or more substituents selected from the group consisting of: 1 But the group G 11 A compound in which R is a 5- or 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from the group consisting of: 1 But the group G 11 A is a single bond, —CH—, or —NR 6 - and R 6 is a C1-C3 alkyl group or a hydrogen atom. 1 But the group G 11A compound in which A is a phenyl group optionally substituted with one or more substituents selected from the group consisting of: 1 But the group G 11 A compound in which A is a phenyl group optionally substituted with one or more substituents selected from the group consisting of: 1 But the group G 11 A compound in which R is a 5- or 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from the group consisting of: 1 But the group G 11 A is a single bond, —CH—, or —NR 6 - and R 6 is a C1-C3 alkyl group or a hydrogen atom. 1 But the group G 11 A compound in which A is a phenyl group optionally substituted with one or more substituents selected from the group consisting of: 1 But the group G 11 A compound in which A is a phenyl group optionally substituted with one or more substituents selected from the group consisting of: 1 But the group G 11 and A is a single bond. [Embodiment 121] A compound according to any one of embodiments 1 to 120 or the compound of the present invention, wherein R 3 But the group G 4 a phenyl group optionally substituted with 1 to 3 substituents selected from the group G 4 [Embodiment 122] A compound according to any one of embodiments 1 to 120 or the present compound, wherein R 3 But the group G 41 Group G: Compounds each of which is a phenyl group optionally substituted with one or two substituents selected from the following: 41The group consisting of a nitro group, a halogen atom, a cyano group, a methyl group, an ethyl group, an isopropyl group, a cyclopropyl group (the cyclopropyl group may be substituted with one or more substituents selected from the group consisting of a halogen atom and a cyano group), a trifluoromethyl group, a difluoromethyl group, a methoxy group, a trifluoromethoxy group, a difluoromethoxy group, a methylthio group, a methylsulfinyl group, a methylsulfonyl group, a trifluoromethylthio group, a trifluoromethylsulfinyl group, a trifluoromethylsulfonyl group, a difluoromethylthio group, a difluoromethylsulfinyl group, and a difluoromethylsulfonyl group. [Embodiment 123] In embodiments 1 to 120 or the compound of the present invention, R 3 is a phenyl group optionally substituted with 1 or 2 halogen atoms. [Embodiment 124] A compound according to any one of embodiments 1 to 120 or the compound of the present invention, wherein R 3 But the group G 41 [Embodiment 125] A compound according to any one of embodiments 1 to 120 or the present compound, wherein R 3 is a 6-membered aromatic heterocyclic group optionally substituted with 1 or 2 halogen atoms. [Embodiment 126] A compound according to any one of embodiments 1 to 120 or compound N of the present invention, wherein R 3 Formula (R-3) [wherein ● represents a binding site, R ３Ａ , R ３Ｂ , R ３Ｃ , R ３Ｄ , and R ３Ｅ are the same or different and represent a C1-C3 alkyl group optionally substituted with one or more halogen atoms, a C1-C3 alkoxy group optionally substituted with one or more halogen atoms, a C3-C5 cycloalkyloxy group optionally substituted with one or more halogen atoms, a nitro group, a halogen atom, a cyano group, or a hydrogen atom. [Aspect 127] A compound in aspect 126, wherein R ３Ａ and R ３Ｅ is a hydrogen atom. ３Ａ and R ３Ｅ is a hydrogen atom, and R ３Ｂ , R ３Ｃ , and R３Ｄ are the same or different and are a C1-C3 alkyl group optionally substituted with one or more halogen atoms, a C1-C3 alkoxy group optionally substituted with one or more halogen atoms, a halogen atom, or a hydrogen atom. ３Ａ and R ３Ｅ is a hydrogen atom, and R ３Ｂ and R ３Ｄ are the same or different and are a halogen atom or a hydrogen atom, and R ３Ｃ is a C1-C3 alkyl group optionally substituted with one or more halogen atoms, a C1-C3 alkoxy group optionally substituted with one or more halogen atoms, a halogen atom, or a hydrogen atom. ３Ａ and R ３Ｅ is a hydrogen atom, and R ３Ｂ and R ３Ｄ are the same or different and are a halogen atom or a hydrogen atom, and R ３Ｃ is a C1-C3 alkyl group substituted with one or more halogen atoms, a C1-C3 alkoxy group substituted with one or more halogen atoms, a halogen atom, or a hydrogen atom. ３Ａ and R ３Ｅ is a hydrogen atom, and R ３Ｂ and R ３Ｄ are the same or different and are a halogen atom or a hydrogen atom, and R ３Ｃ is a methyl group, a trifluoromethyl group, a methoxy group, a trifluoromethoxy group, a difluoromethoxy group, a halogen atom, or a hydrogen atom. ３Ａ and R ３Ｅ is a hydrogen atom, and R ３Ｂ and R ３Ｄ are the same or different and are a halogen atom or a hydrogen atom, and R ３Ｃ is a trifluoromethoxy group, a halogen atom, or a hydrogen atom. ３Ａ , R ３Ｂ , R ３Ｄ and R ３Ｅ is a hydrogen atom, and R ３Ｃis a trifluoromethoxy group, a halogen atom, or a hydrogen atom. ３Ａ and R ３Ｅ is a hydrogen atom, and R ３Ｂ and R ３Ｄ are the same or different and are hydrogen atoms, and R ３Ｃ is a trifluoromethoxy group, a fluorine atom, a chlorine atom, or a hydrogen atom. ３Ａ and R ３Ｅ is a hydrogen atom, and R ３Ｂ and R ３Ｄ is a fluorine atom, a chlorine atom, or a hydrogen atom, and R ３Ｃ is a trifluoromethoxy group, a fluorine atom, a chlorine atom, or a hydrogen atom. ３Ａ and R ３Ｅ is a hydrogen atom, and R ３Ｂ and R ３Ｄ is a fluorine atom, a chlorine atom, or a hydrogen atom, and R ３Ｃ is a fluorine atom, a chlorine atom, or a hydrogen atom. ２ is a cyclopropyl group. [Embodiment 138] In the compound N of the present invention, R ２ is an n-propyl group. [Embodiment 139] In the compound N of the present invention, R ２ is an ethyl group. [Embodiment 140] In the compound N of the present invention, R ２ [Embodiment 141] Compound N of the present invention, wherein A is a single bond, —CH ２ A compound of the present invention N, wherein A is a single bond or an oxygen atom. [Embodiment 142] A compound of the present invention N, wherein A is -CH ２ -, or an oxygen atom. [Embodiment 144] In the compound N of the present invention, R １ But the group G １１ A is a phenyl group optionally substituted with one or more substituents selected from the group consisting of a single bond, —CH ２- or an oxygen atom, and R6 is a C1-C3 alkyl group or a hydrogen atom. １ But the group G １１ A is a phenyl group optionally substituted with one or more substituents selected from the group consisting of -CH ２ - or an oxygen atom, and R6 is a C1-C3 alkyl group or a hydrogen atom. １ But the group G １１ A compound in which A is a phenyl group optionally substituted with one or more substituents selected from the group consisting of: A is a single bond or an oxygen atom; and R6 is a C1-C3 alkyl group or a hydrogen atom. １ But the group G １１ A compound in which A is an oxygen atom, and R is a phenyl group optionally substituted with one or more substituents selected from the group consisting of: １ But the group G １１ A is a 5- or 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from the group consisting of: ２ [Embodiment 149] In the compound N of the present invention, R １ But the group G １１ A is a 5- or 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from the group consisting of: ２ [Embodiment 150] In the compound N of the present invention, R １ is a group represented by formula C-1 [wherein ● represents the bonding site with A, G １１ａ , G １１ｂ , and G １１ｃ are the same or different, and the group G １１ represents a methine group optionally substituted with one or more substituents selected from the group consisting of: ２ [Embodiment 151] In the compound N of the present invention, R １ is a 5-membered aromatic heterocyclic group represented by formula C-1, and A is —CH ２ [Embodiment 152] In the compound N of the present invention, R １is a 5-membered aromatic heterocyclic group represented by formula C-1, and A is a single bond. １ But the group G ４ [Embodiment 154] In the compound N of the present invention, R １ is a pyridyl group. ２ is an ethyl group. ２ is an isopropyl group. ２ is an ethyl group. ２ is an isopropyl group. ２ is an ethyl group. ２ is an isopropyl group. ２ is an ethyl group. ２ is an isopropyl group. ２ is an ethyl group. ２ is an isopropyl group. ２ is an ethyl group. ２ is an isopropyl group. ２ is an ethyl group. ２ is an isopropyl group. ２ is an ethyl group. ２ is an isopropyl group. ２ is an ethyl group. ２ is an isopropyl group.２ is an ethyl group. ２ is an isopropyl group. １ But the group G １１ A is a phenyl group optionally substituted with one or more substituents selected from the group consisting of -CH ２ -, or an oxygen atom. １ But the group G １１ A compound in which A is a phenyl group optionally substituted with one or more substituents selected from the group consisting of: １ But the group G １１ and A is an oxygen atom. １ But the group G １１ A is a 5- or 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from the group consisting of: ２ [Embodiment 179] In embodiment 24, R １ But the group G １１ A is a phenyl group optionally substituted with one or more substituents selected from the group consisting of a single bond, —CH ２ -, or an oxygen atom. １ But the group G １１ A is a phenyl group optionally substituted with one or more substituents selected from the group consisting of -CH ２ -, or an oxygen atom. １ But the group G １１ A compound in which A is a phenyl group optionally substituted with one or more substituents selected from the group consisting of: １ But the group G １１ A compound in which A is an oxygen atom, and R is a phenyl group optionally substituted with one or more substituents selected from the group consisting of １ But the group G １１A is a 5- or 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from the group consisting of: ２ [Embodiment 184] In embodiment 27, R １ But the group G １１ A is a phenyl group optionally substituted with one or more substituents selected from the group consisting of a single bond, —CH ２ -, or an oxygen atom. １ But the group G １１ A is a phenyl group optionally substituted with one or more substituents selected from the group consisting of -CH ２ -, or an oxygen atom. １ But the group G １１ and A is a single bond or an oxygen atom. １ But the group G １１ and A is an oxygen atom. １ But the group G １１ A is a 5- or 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from the group consisting of: ２ [Embodiment 189] In embodiment 28, R １ But the group G １１ A is a phenyl group optionally substituted with one or more substituents selected from the group consisting of a single bond, —CH ２ -, or an oxygen atom. １ But the group G １１ A is a phenyl group optionally substituted with one or more substituents selected from the group consisting of -CH ２ -, or an oxygen atom. １ But the group G １１ A compound in which A is a phenyl group optionally substituted with one or more substituents selected from the group consisting of: １ But the group G １１A compound in which A is an oxygen atom, and R is a phenyl group optionally substituted with one or more substituents selected from the group consisting of １ But the group G １１ A is a 5- or 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from the group consisting of: ２ [Embodiment 194] In embodiment 29, R １ But the group G １１ A is a phenyl group optionally substituted with one or more substituents selected from the group consisting of a single bond, —CH ２ -, or an oxygen atom. １ But the group G １１ A is a phenyl group optionally substituted with one or more substituents selected from the group consisting of -CH ２ -, or an oxygen atom. １ But the group G １１ A compound in which A is a phenyl group optionally substituted with one or more substituents selected from the group consisting of: １ But the group G １１ A compound in which A is an oxygen atom, and R is a phenyl group optionally substituted with one or more substituents selected from the group consisting of １ But the group G １１ A is a 5- or 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from the group consisting of: ２ [Embodiment 199] In embodiment 139, R １ But the group G １１ A is a phenyl group optionally substituted with one or more substituents selected from the group consisting of a single bond, —CH ２ - or -NR ６ - and R ６ is a C1-C3 alkyl group or a hydrogen atom. １ But the group G １１ A is a phenyl group optionally substituted with one or more substituents selected from the group consisting of a single bond and -CH ２[Embodiment 201] In embodiment 139, R １ But the group G １１ A is a phenyl group optionally substituted with one or more substituents selected from the group consisting of -CH ２ [Embodiment 202] In embodiment 139, R １ But the group G １１ and A is a single bond. [Aspect 203] In aspect 139, R １ But the group G １１ A is a phenyl group optionally substituted with one or more substituents selected from the group consisting of a single bond, —CH ２ -, or an oxygen atom. １ But the group G １１ A is a phenyl group optionally substituted with one or more substituents selected from the group consisting of -CH ２ -, or an oxygen atom. １ But the group G １１ and A is a single bond or an oxygen atom. １ But the group G １１ and A is an oxygen atom. １ But the group G １１ A is a 5- or 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from the group consisting of: ２ [Embodiment 208] In embodiment 140, R １ But the group G １１ A is a phenyl group optionally substituted with one or more substituents selected from the group consisting of a single bond, —CH ２ - or -NR ６ - and R ６ is a C1-C3 alkyl group or a hydrogen atom. １ But the group G １１A is a phenyl group optionally substituted with one or more substituents selected from the group consisting of a single bond and -CH ２ [Embodiment 210] In embodiment 140, R １ But the group G １１ A is a phenyl group optionally substituted with one or more substituents selected from the group consisting of -CH ２ [Embodiment 211] In embodiment 140, R １ But the group G １１ and A is a single bond. [Embodiment 212] In embodiment 140, R １ But the group G １１ A is a phenyl group optionally substituted with one or more substituents selected from the group consisting of a single bond, —CH ２ -, or an oxygen atom. １ But the group G １１ A is a phenyl group optionally substituted with one or more substituents selected from the group consisting of -CH ２ -, or an oxygen atom. １ But the group G １１ and A is a single bond or an oxygen atom. １ But the group G １１ and A is an oxygen atom. １ But the group G １１ A is a 5- or 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from the group consisting of: ２ [Embodiment 217] In embodiment 11, R ２ is an ethyl group. ２ is an isopropyl group. ２ is an ethyl group. ２is an isopropyl group. ２ is an ethyl group. ２ is an isopropyl group. ２ is an ethyl group. ２ is an isopropyl group. ２ is an ethyl group. ２ is an isopropyl group. ２ is an ethyl group. ２ is an isopropyl group. ２ is an ethyl group. ２ is an isopropyl group. ２ is an ethyl group. ２ is an isopropyl group. ２ is an isopropyl group. ２ is an ethyl group. １ But the group G １１ A is a phenyl group optionally substituted with one or more substituents selected from the group consisting of a single bond, —CH ２ -, or an oxygen atom. １ But the group G １１ A is a phenyl group optionally substituted with one or more substituents selected from the group consisting of -CH ２ -, or an oxygen atom. １ But the group G １１A compound in which A is a phenyl group optionally substituted with one or more substituents selected from the group consisting of: １ But the group G １１ and A is an oxygen atom. １ But the group G １１ A is a 5- or 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from the group consisting of: ２ [Embodiment 239] In embodiment 46, R １ But the group G １１ A is a phenyl group optionally substituted with one or more substituents selected from the group consisting of a single bond, —CH ２ -, or an oxygen atom. １ But the group G １１ A is a phenyl group optionally substituted with one or more substituents selected from the group consisting of -CH ２ -, or an oxygen atom. １ But the group G １１ A compound in which A is a phenyl group optionally substituted with one or more substituents selected from the group consisting of: １ But the group G １１ and A is an oxygen atom. １ But the group G １１ A is a 5- or 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from the group consisting of: ２ [Embodiment 244] In embodiment 47, R １ But the group G １１ A is a phenyl group optionally substituted with one or more substituents selected from the group consisting of a single bond, —CH ２ -, or an oxygen atom. １ But the group G １１A is a phenyl group optionally substituted with one or more substituents selected from the group consisting of -CH ２ -, or an oxygen atom. １ But the group G １１ A compound in which A is a phenyl group optionally substituted with one or more substituents selected from the group consisting of: １ But the group G １１ A compound in which R is a phenyl group optionally substituted with one or more substituents selected from the group consisting of １ But the group G １１ A is a 5- or 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from the group consisting of: ２ [Embodiment 249] In embodiment 173, R １ But the group G １１ A is a phenyl group optionally substituted with one or more substituents selected from the group consisting of a single bond, —CH ２ - or -NR ６ - and R ６ is a C1-C3 alkyl group or a hydrogen atom. １ But the group G １１ A is a phenyl group optionally substituted with one or more substituents selected from the group consisting of a single bond and -CH ２ [Embodiment 251] In embodiment 173, R １ But the group G １１ A is a phenyl group optionally substituted with one or more substituents selected from the group consisting of -CH ２ [Embodiment 252] In embodiment 173, R １ But the group G １１ and A is a single bond. １ But the group G １１ A is a phenyl group optionally substituted with one or more substituents selected from the group consisting of a single bond, —CH ２-, or an oxygen atom. １ But the group G １１ A is a phenyl group optionally substituted with one or more substituents selected from the group consisting of -CH ２ -, or an oxygen atom. １ But the group G １１ and A is a single bond or an oxygen atom. １ But the group G １１ and A is an oxygen atom. １ But the group G １１ A is a 5- or 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from the group consisting of: ２ [Embodiment 258] In embodiment 174, R １ But the group G １１ A is a phenyl group optionally substituted with one or more substituents selected from the group consisting of a single bond, —CH ２ - or -NR ６ - and R ６ is a C1-C3 alkyl group or a hydrogen atom. １ But the group G １１ A is a phenyl group optionally substituted with one or more substituents selected from the group consisting of a single bond and -CH ２ [Embodiment 260] In embodiment 174, R １ But the group G １１ A is a phenyl group optionally substituted with one or more substituents selected from the group consisting of -CH ２ [Embodiment 261] In embodiment 174, R １ But the group G １１ and A is a single bond. [Embodiment 262] In embodiment 174, R １ But the group G １１A is a phenyl group optionally substituted with one or more substituents selected from the group consisting of a single bond, —CH ２ -, or an oxygen atom. １ But the group G １１ A is a phenyl group optionally substituted with one or more substituents selected from the group consisting of -CH ２ -, or an oxygen atom. １ But the group G １１ and A is a single bond or an oxygen atom. １ But the group G １１ and A is an oxygen atom. １ But the group G １１ A is a 5- or 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from the group consisting of: ２ [Embodiment 267] In embodiment 66, R １ But the group G １１ A is a phenyl group optionally substituted with one or more substituents selected from the group consisting of a single bond, —CH ２ -, or an oxygen atom. １ But the group G １１ A is a phenyl group optionally substituted with one or more substituents selected from the group consisting of -CH ２ -, or an oxygen atom. １ But the group G １１ and A is a single bond or an oxygen atom. １ But the group G １１ and A is an oxygen atom. １ But the group G １１A is a 5- or 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from the group consisting of: ２ [Embodiment 272] In embodiment 233, R １ But the group G １１ A is a phenyl group optionally substituted with one or more substituents selected from the group consisting of a single bond, —CH ２ -, or an oxygen atom. １ But the group G １１ A is a phenyl group optionally substituted with one or more substituents selected from the group consisting of -CH ２ -, or an oxygen atom. １ But the group G １１ and A is a single bond or an oxygen atom. １ But the group G １１ and A is an oxygen atom. １ But the group G １１ A is a 5- or 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from the group consisting of: ２ [Embodiment 278] In the embodiment 1 to 120, 137 to 276, or the compound N of the present invention, R ３ is a group represented by formula D1-1, formula D-1-2, or formula D-2-1 (wherein ● represents a bonding site with a nitrogen atom, R ３８ａ , R ３８ｂ , R ３８ｃ , R ３８ｄ , R ３８ｅ , R ３８ｆ is a hydrogen atom or a group G ４ [Embodiment 279] In embodiment 278 or compound N of the present invention, R ３８ａ , R ３８ｂ , R ３８ｃ , R ３８ｄ , R ３８ｅ , R ３８ｆ is a hydrogen atom or a group G ４１[Embodiment 280] In Embodiments 1 to 120, 137 to 276, or compound N of the present invention, R ３ is a group represented by the following formula D-3 (wherein ● represents a bonding site with a nitrogen atom, R ３９ａ , R ３９ｂ , R ３９ｃ , R ３９ｄ is a hydrogen atom or a group G ４ [Embodiment 281] In embodiment 280, R ３９ａ , R ３９ｂ , R ３９ｃ , R ３９ｄ is a hydrogen atom or a group G ４１ [Embodiment 282] In embodiment 280, R ３９ａ , R ３９ｃ , R ３９ｄ is a hydrogen atom. [Embodiment 283] In the embodiment 1 to 120, 137 to 276, 280 to 282, or the compound N of the present invention, R ３ is a pyridyl group optionally substituted with 1 or 2 halogen atoms. [Embodiment 284] In any one of embodiments 1 to 120, 137 to 276, 280 to 282, or compound N of the present invention, R ３ is a pyridyl group optionally substituted with one or two C1-C3 alkyl groups. [Embodiment 285] In any one of embodiments 1 to 120, 137 to 276, 280 to 282, or compound N of the present invention, R ３ is a pyridyl group optionally substituted with a C3-C6 cycloalkyl group. [Embodiment 286] In any one of embodiments 1 to 120, 137 to 276, 280 to 282, or compound N of the present invention, R ３ is a pyridyl group optionally substituted with one C1-C3 alkoxy group. [Embodiment 287] In any one of embodiments 1 to 120, 137 to 276, 280 to 282, or compound N of the present invention, R ３ is a pyridyl group optionally substituted with one C1-C3 haloalkoxy group. [Embodiment 288] In embodiments 1 to 120, 137 to 276, 280 to 282, or compound N of the present invention, ４１[Embodiment 289] A compound according to any one of embodiments 1 to 120, 137 to 276, or compound N of the present invention, wherein R ３ is the group G ４ [Embodiment 290] A compound according to any one of embodiments 1 to 120, 137 to 276, or compound N of the present invention, wherein R is an imidazolyl group, a triazolyl group, a thiazolyl group, a pyrimidinyl group, or a pyridazinyl group, each of which may be substituted with one or more substituents selected from the group consisting of: ３ is a group represented by formula B1-2. [Aspect 291] In aspect 290, G ７ａ２ and G ７ｃ２ is an oxygen atom. [Embodiment 292] In embodiment 291, G ７ｂ２ Ga-CF ２ [Embodiment 293] In embodiments 1 to 120, 137 to 276, or compound N of the present invention, R ３ is an 8-membered aromatic heterocyclic group. [Embodiment 294] In embodiments 1 to 120, 137 to 276, or compound N of the present invention, R ３ is a 9-membered aromatic heterocyclic group. [Embodiment 295] In embodiments 1 to 120, 137 to 276, or compound N of the present invention, R ３ is a 10-membered aromatic heterocyclic group. [Embodiment 296] In embodiments 1 to 120, 137 to 276, 295 or compound N of the present invention, R ３ is a group represented by any one of the formulas E-1 to E-8 (wherein ● represents a bonding site with a nitrogen atom, R ４０ａ , R ４０ｂ , R ４０ｃ , R ４０ｄ , R ４０ｅ , R ４０ｆ , and R ４０ｇ are the same or different and each represents a hydrogen atom or a group G ４１ [Embodiment 297] In the embodiment 1 to 120, 137 to 276, 295, 296 or compound N of the present invention, R 3 is a group represented by any one of formulas E-1-1, E-2-1, E-3-1, E-4-1, E-5-1, E-6-1, and E-7-1 (wherein ● represents a bonding site to a nitrogen atom). [Embodiment 298] In embodiments 1 to 120, 137 to 276, 295 to 297 or compound N of the present invention, R 3 is a group represented by formula E-4-2 or E-7-2. (wherein ● represents a bonding site to a nitrogen atom). [Embodiment 299] In embodiments 1 to 120, 137 to 276, 294 or compound N of the present invention, R 3 is a group represented by formulae F-1 to F-12. (wherein ● represents a bonding site with a nitrogen atom, R ４１ａ , R ４１ｂ , R ４１ｃ , R ４１ｄ , R ４１ｅ , R ４１ｆ , and R ４１ｇ are the same or different and each represents a hydrogen atom or a group G ４１ R represents a substituent selected from ４２ represents a hydrogen atom, a C1-C3 alkyl group optionally substituted with one or more halogen atoms, or a C3-C6 cycloalkyl group optionally substituted with one or more halogen atoms. [Embodiment 300] In Embodiments 1 to 120, 137 to 276, 294, 300 or Compound N of the present invention, R 3 is a group represented by formula F-1-1, F-2-1, F-3-1, F-4-1, F-5-1, F-6-1, F-7-1, F-8-1, F-9-1, F-10-1, F-11-1, F-12-1 (wherein ● represents a bonding site to the nitrogen atom). [Embodiment 301] In embodiments 1 to 120, 137 to 276, 294, 300, 301, or the compound of the present invention, R 3 is a group represented by formula F-1-2, F-2-2, F-3-2, F-3-3, F-4-2, F-4-3, F-5-2, F-6-2, F-7-2, F-9-2, F-10-2 (wherein the ● represents the bonding site with the nitrogen atom).

[0016] Next, the methods for producing the compounds of the present invention and their intermediates will be explained.

[0017] Production Method A The compound represented by formula (I-1) (hereinafter referred to as compound (I-1)) can be produced by reacting a compound represented by formula (A1) (hereinafter referred to as compound (A1)) with a compound represented by formula (M1) (hereinafter referred to as compound (M1)) in the presence of a catalyst and a base. [During the ceremony, W 1 represents a chlorine atom, a bromine atom, or an iodine atom; M 1 is an alkoxyboranyl group such as B(OH)2, 4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl group, or a trifluoroborate salt (BF3 - K + ) and A a represents —CH—, —C(═CH)—, or a single bond, and R 15a represents a C1-C10 chain hydrocarbon group optionally substituted with one or more halogen atoms, a C3-C6 alicyclic hydrocarbon group optionally substituted with one or more halogen atoms, or a benzyl group {the phenyl moiety in the benzyl group is selected from the group G 6and the methylene moiety may be substituted with one or two C1-C3 alkyl groups}, and the other symbols have the same meanings as above.] The reaction is usually carried out in a single solvent or a mixed solvent. Examples of solvents used in the reaction include hydrocarbons such as toluene, xylene, hexane, etc. (hereinafter referred to as hydrocarbons); ethers such as methyl tert-butyl ether (hereinafter referred to as MTBE), tetrahydrofuran (hereinafter referred to as THF), 1,4-dioxane, etc. (hereinafter referred to as ethers); halogenated hydrocarbons such as dichloromethane, chloroform, chlorobenzene, etc. (hereinafter referred to as halogenated hydrocarbons); amides such as N,N-dimethylformamide (hereinafter referred to as DMF, etc. (hereinafter referred to as amides); esters such as ethyl acetate (hereinafter referred to as esters); nitriles such as acetonitrile (hereinafter referred to as nitriles); water; and mixtures of two or more of these. Examples of catalysts used in the reaction include palladium catalysts such as tetrakistriphenylphosphinepalladium(0), palladium(II) acetate, tris(dibenzylideneacetone)dipalladium, and [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride. Examples of bases used in the reaction include organic bases such as triethylamine, diisopropylethylamine, 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), pyridine, and 4-(dimethylamino)pyridine (hereinafter referred to as organic bases); alkali metal carbonates such as sodium carbonate and potassium carbonate (hereinafter referred to as alkali metal carbonates); alkali metal bicarbonates such as potassium bicarbonate (hereinafter referred to as alkali metal bicarbonates); alkaline earth metal carbonates such as magnesium carbonate and calcium carbonate (hereinafter referred to as alkaline earth metal carbonates); sodium fluoride and tripotassium phosphate. In the reaction, compound (M1) is usually used in a ratio of 1 to 10 moles, catalyst is usually used in a ratio of 0.01 to 1 mole, and base is usually used in a ratio of 1 to 10 moles, relative to 1 mole of compound (A1). The reaction temperature is usually within the range of 0 to 150°C. The reaction time is usually within the range of 0.1 to 120 hours.After the reaction is complete, the reaction mixture is mixed with water, extracted with an organic solvent, and post-treatments such as drying and concentrating the organic layer can be performed to isolate compound (I-1). Compound (M1) is a commercially available compound, or can be produced by the method described in Chemical Reviews, Vol. 95, pp. 2457-2483 (1995), or a method analogous thereto. Boronic acid derivatives can also be produced by hydrolyzing, as necessary, boronate ester derivatives obtained by these methods or commercially available boronic acid ester derivatives. Furthermore, the boronate ester can be fluorinated to give trifluoroborate salts (BF3) according to methods described in literature such as Accounts of Chemical Research, Vol. 40, pp. 275-286 (2007). - K + ) can also be obtained.

[0018] Production Method B The compound represented by formula (I-2) (hereinafter referred to as compound (I-2)) can be produced by reacting compound (A1) with a compound represented by formula (M2) (hereinafter referred to as compound (M2)) in the presence of one or more catalysts and one or more bases. [In the formula, A b represents an oxygen atom, a sulfur atom, -NR 6- group or a single bond, and other symbols have the same meanings as above.] The reaction is usually carried out in a single solvent or a mixed solvent. Examples of solvents used in the reaction include hydrocarbons; ethers; halogenated hydrocarbons; amides; esters; nitriles; water; and mixtures of two or more of these. Examples of catalysts used in the reaction include palladium catalysts such as tetrakis(triphenylphosphine)palladium(0), 1,1'-bis(diphenylphosphino)ferrocenepalladium(II) dichloride, tris(dibenzylideneacetone)dipalladium(0), and palladium(II) acetate; nickel catalysts such as bis(cyclooctadiene)nickel(0) and nickel(II) chloride; and copper catalysts such as copper(I) iodide and copper(I) chloride. Examples of the base used in the reaction include organic bases; alkali metal carbonates; alkaline earth metal carbonates; alkali metal hydrogencarbonates; metal carboxylates such as sodium acetate, potassium acetate, calcium acetate, magnesium acetate, and the like (hereinafter referred to as metal carboxylates); metal alkoxides such as sodium methoxide, sodium ethoxide, sodium tert-butoxide, potassium methoxide, and potassium tert-butoxide (hereinafter referred to as metal alkoxides); metal hydroxides such as sodium hydroxide, potassium hydroxide, calcium hydroxide, magnesium hydroxide, and the like (hereinafter referred to as metal hydroxides); and metal hydrides such as lithium hydride, sodium hydride, potassium hydride, and calcium hydride (hereinafter referred to as metal hydrides). A ligand can also be used in the reaction, if necessary.Examples of the ligand include triphenylphosphine, xantphos, 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl, 1,1'-bis(diphenylphosphino)ferrocene, 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl, 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 1,2-bis(diphenylphosphino)ethane, N,N'-dimethylethylenediamine, N,N,N'-trimethylethylenediamine, trans-N,N'-dimethylcyclohexane-1,2-diamine, 2,2'-bipyridine, 2-aminoethanol, 8-hydroxyquinoline, and 1,10-phenanthroline. When a ligand is used in the reaction, the ligand is usually used in a ratio of 0.01 to 1 mole per mole of compound (A1). In the reaction, compound (M2) is typically used in a ratio of 1 to 10 moles, catalyst typically in a ratio of 0.01 to 1 mole, and base typically in a ratio of 1 to 10 moles per mole of compound (A1). The reaction temperature is typically within the range of -20 to 200°C. The reaction time is typically within the range of 0.1 to 120 hours. After completion of the reaction, compound (I-2) can be isolated by mixing the reaction mixture with water, extracting it with an organic solvent, and performing post-treatment operations such as drying and concentrating the organic layer. Compound (M2) is a commercially available compound or can be produced according to known methods.

[0019] Production Method C-1 The compound represented by formula (I-3) (hereinafter referred to as compound (I-3)) can be produced by reacting a compound represented by formula (I-1-1) (hereinafter referred to as compound (I-1-1)) with a compound represented by formula (M3) (hereinafter referred to as compound (M3)) in the presence of a base. [In the formula, R 4a represents a C1-C3 alkyl group optionally substituted with one or more halogen atoms, L 1represents a leaving group such as a halogen atom, a methanesulfonyloxy group, a trifluoromethylsulfonyloxy group, a 4-methylphenylsulfonyloxy group, or a phenylsulfonyloxy group, and other symbols have the same meaning as above.] The reaction is usually carried out in a single solvent or a mixed solvent. Examples of solvents used in the reaction include hydrocarbons; ethers; halogenated hydrocarbons; amides; esters; nitriles; alcohols such as methanol and ethanol (hereinafter referred to as alcohols); ketones such as acetone and methyl isobutyl ketone (hereinafter referred to as MIBK) (hereinafter referred to as ketones); water; and mixtures of two or more thereof. Examples of bases used in the reaction include organic bases; alkali metal carbonates; alkaline earth metal carbonates; alkali metal hydrogencarbonates; metal carboxylates; metal hydroxides; and metal hydrides. In the reaction, compound (M3) is usually used in a ratio of 1 to 10 moles, and a base is usually used in a ratio of 1 to 10 moles, relative to 1 mole of compound (I-1-1). The reaction temperature is usually within the range of -20 to 200°C. The reaction time is usually within the range of 0.1 to 120 hours. After completion of the reaction, the reaction mixture is mixed with water, extracted with an organic solvent, and the organic layer is dried, concentrated, and other post-treatment procedures are carried out to isolate compound (I-3). Compound (M3) is a commercially available compound, or can be produced according to known methods.

[0020] Production Method C-2 The compound represented by formula (I-4) (hereinafter referred to as compound (I-4)) can be produced by reacting compound (I-3) with a compound represented by formula (M4) (hereinafter referred to as compound (M4)) in the presence of a base. [In the formula, R 5a represents a C1-C3 alkyl group optionally substituted with one or more halogen atoms, and the other symbols have the same meanings as above.] The reaction can be carried out in accordance with Production Method C-1, using compound (I-3) instead of compound (I-1-1) and compound (M4) instead of compound (M3). Compound (M4) is a commercially available compound, or can be produced in accordance with known methods.

[0021] Production Method C-3 The compound represented by formula (I-5) (hereinafter referred to as compound (I-5)) can be produced by reacting compound (I-1-1) with a compound represented by formula (M5) (hereinafter referred to as compound (M5)) in the presence of a base. [wherein r represents an integer of 1 to 4, L 2 represents a leaving group such as a halogen atom, a methanesulfonyloxy group, a trifluoromethylsulfonyloxy group, a 4-methylphenylsulfonyloxy group, or a phenylsulfonyloxy group, and other symbols have the same meanings as above.] The reaction can be carried out in accordance with Production Method C-1, except that compound (M5) is used in place of compound (M3). Compound (M5) is a commercially available compound, or can be produced in accordance with known methods.

[0022] Production Method D The compound represented by formula (I-6) (hereinafter referred to as compound (I-6)) can be produced by reacting a compound represented by formula (I-1-2) (hereinafter referred to as compound (I-1-2)) with hydrogen in the presence of a hydrogenation catalyst. [In the formula, the symbols have the same meanings as above.] The reaction is usually carried out in a solvent under a hydrogen atmosphere at 1 to 100 atmospheres. Examples of solvents used in the reaction include alcohols; esters; halogenated hydrocarbons; ethers; hydrocarbons; water; and mixtures of two or more of these. Examples of hydrogenation catalysts used in the reaction include transition metal catalysts such as palladium on carbon (Pd / C), platinum on carbon (Pt / C), Raney nickel, and palladium hydroxide, as well as compounds thereof. The reaction can also be carried out, if necessary, by adding an acid or a base. Examples of acids include acetic acid and hydrochloric acid, and examples of bases include tertiary amines such as triethylamine and magnesium oxide. In the reaction, the hydrogenation catalyst is usually used in a ratio of 0.001 to 1 mole, and hydrogen is usually used in a ratio of 1 mole or more, relative to 1 mole of compound (I-1-2). When an acid or a base is used in the reaction, the acid is usually used in a ratio of 0.001 to 10 moles, and the base is usually used in a ratio of 1 to 10 moles. The reaction temperature is usually within the range of −20 to 150° C. The reaction time is usually within the range of 0.1 to 120 hours. After completion of the reaction, the catalyst is filtered off, and then the filtrate is concentrated, whereby compound (I-6) can be isolated.

[0023] Production Method E The compound represented by formula (I-8) (hereinafter referred to as compound (I-8)) can be produced by reacting a compound represented by formula (I-7) (hereinafter referred to as compound (I-7)) in the presence of a reducing agent. [In the formula, the symbols have the same meanings as defined above.] The reaction is usually carried out in a single solvent or a mixed solvent. Examples of solvents used in the reaction include hydrocarbons; ethers; halogenated hydrocarbons; amides; esters; nitriles; alcohols; water; and mixtures of two or more of these. Examples of reducing agents used in the reaction include borohydride salts such as sodium borohydride and potassium borohydride. The reducing agent is usually used in a ratio of 0.3 to 1.5 moles per mole of compound (I-7) in the reaction. The reaction temperature is usually within the range of −20 to 200°C. The reaction time is usually within the range of 0.1 to 120 hours. After completion of the reaction, compound (I-8) can be isolated by post-treatment such as mixing the reaction mixture with water, extracting it with an organic solvent, and drying and concentrating the organic layer.

[0024] Production Method E The compound represented by formula (I-9) (hereinafter referred to as compound (I-9)) can be produced by reacting compound (I-8) with compound (M3) in the presence of a base. [wherein the symbols have the same meanings as defined above.] The reaction can be carried out according to Production Method C-1, except that compound (I-8) is used in place of compound (I-1-1).

[0025] Production Method F Compound (I-7) can be produced by reacting a compound represented by formula (I-10) (hereinafter referred to as compound (I-10)) with a compound represented by formula (M6) (hereinafter referred to as compound (M6)) in the presence of a base. [In the formula, the symbols have the same meanings as defined above.] The reaction is usually carried out in a single solvent or a mixed solvent. Examples of solvents used in the reaction include hydrocarbons; ethers; halogenated hydrocarbons; amides; imidazolinones such as 1,3-dimethyl-2-imidazolinone; sulfoxides (hereinafter referred to as sulfoxides) such as dimethyl sulfoxide (hereinafter referred to as DMSO); nitriles; water; and mixtures of two or more thereof. Examples of bases used in the reaction include organic bases; alkali metal carbonates; alkaline earth metal carbonates; alkali metal hydrogencarbonates; metal carboxylates; metal alkoxides; metal hydroxides; and metal hydrides. In the reaction, compound (M6) is usually used in a ratio of 1 to 10 moles and a base is usually used in a ratio of 1 to 10 moles per mole of compound (I-10). The reaction temperature is usually within the range of −20 to 200° C. The reaction time is usually within the range of 0.1 to 120 hours. After the reaction is complete, the reaction mixture is mixed with water, extracted with an organic solvent, and the organic layer is dried, concentrated, and other post-treatment procedures are carried out to isolate compound (I-7). Compound (M6) is a commercially available compound, or can be prepared according to known methods.

[0026] Production Method G Compound (I-10) can be produced according to the following scheme using a compound represented by formula (A2) (hereinafter referred to as compound (A2)) and a compound represented by formula (A3) (hereinafter referred to as compound (A3)). [In the formula, the symbols have the same meanings as defined above.] Each reaction in the above scheme can be carried out according to the method described in U.S. Pat. No. 2,454,742. Compound (A2) is a commercially available compound or can be produced according to a known method. Compound (A3) is a commercially available compound or can be produced according to the method described in Journal of the Chemical Society 1963, 4483-4489.

[0027] Production Method H-1 The compound represented by formula (I-12) (hereinafter referred to as compound (I-12)) can be produced by reacting a compound represented by formula (I-11) (hereinafter referred to as compound (I-11)) in the presence of a base. [In the formula, the symbols have the same meanings as defined above.] The reaction is usually carried out in a single solvent or a mixed solvent. Examples of solvents used in the reaction include ethers; alcohols; water; and mixtures of two or more of these. Examples of bases used in the reaction include organic bases; alkali metal carbonates; alkaline earth metal carbonates; alkali metal hydrogencarbonates; metal carboxylates; and metal hydroxides. The base is usually used in a ratio of 1 to 10 moles per mole of compound (I-11) in the reaction. The reaction temperature is usually within the range of −20 to 200° C. The reaction time is usually within the range of 0.1 to 120 hours. After completion of the reaction, compound (I-12) can be isolated by mixing the reaction mixture with water, extracting it with an organic solvent, and performing post-treatment operations such as drying and concentrating the organic layer.

[0028] Production Method H-2 The compound (I-12) can also be produced by reacting the compound (I-11) in the presence of a lithium salt and an amine. [wherein the symbols have the same meanings as defined above.] The reaction can be carried out according to the method described in Tetrahedron Letters 2007, 48, 2497-2499.

[0029] Production Method H-3 The compound (I-12) can also be produced by reacting the compound (I-11) of the present invention in the presence of an acid. [In the formula, the symbols have the same meanings as defined above.] The reaction is usually carried out in a single solvent or a mixed solvent. Examples of solvents used in the reaction include hydrocarbons; ethers; halogenated hydrocarbons; water; and mixtures of two or more of these. Examples of acids used in the reaction include sulfonic acids such as methanesulfonic acid and p-toluenesulfonic acid (hereinafter referred to as sulfonic acids); inorganic acids such as hydrochloric acid and sulfuric acid (hereinafter referred to as inorganic acids); and carboxylic acids such as acetic acid and trifluoroacetic acid (hereinafter referred to as carboxylic acids). The acid is usually used in a ratio of 0.001 to 10 moles per mole of compound (I-11) in the reaction. The reaction temperature is usually within the range of −20 to 150°C. The reaction time is usually within the range of 0.1 to 120 hours. After completion of the reaction, compound (I-12) can be isolated by mixing the reaction mixture with water, extracting it with an organic solvent, and performing post-treatments such as drying and concentrating the organic layer.

[0030] Production Method I Compound (I-13) can be produced according to the following scheme using a compound represented by formula (A2) (hereinafter referred to as compound (A2)) and a compound represented by formula (A10) (hereinafter referred to as compound (A10)). Each reaction in the above scheme can be carried out in accordance with the method described in Production Method G. (wherein the symbols have the same meanings as defined above.)

[0031] Production Method J Compound (I-15) can be produced using a compound represented by formula (I-14) (hereinafter referred to as compound (I-14)) and a compound represented by formula (M7) (hereinafter referred to as compound (M7)) according to the following scheme. [In the formula, R 2a represents a hydrogen atom, a C1-C7 chain hydrocarbon group optionally substituted with one or more halogen atoms, a C1-C3 alkoxy group optionally substituted with one or more halogen atoms, a C1-C3 alkylthio group optionally substituted with one or more halogen atoms, a C1-C3 alkylsulfinyl group optionally substituted with one or more halogen atoms, a C1-C3 alkylsulfonyl group optionally substituted with one or more halogen atoms, or a cyano group; R 2brepresents a C1-C7 chain hydrocarbon group optionally substituted with one or more halogen atoms, and the other symbols have the same meanings as above.] The reaction is usually carried out in a single solvent or a mixed solvent. Examples of solvents used in the reaction include hydrocarbons; ethers; halogenated hydrocarbons; and mixtures of two or more thereof. Examples of bases used in the reaction include organic bases; alkali metal carbonates; alkaline earth metal carbonates; alkali metal hydrogencarbonates; metal alkoxides; metal hydroxides; and metal hydrides; metal amides, alkyllithiums, and Grignard reagents. In the reaction, compound (M7) is usually used in a ratio of 1 to 10 moles and a base is usually used in a ratio of 1 to 10 moles per mole of compound (I-14). The reaction temperature is usually within the range of −80 to 200°C. The reaction time is usually within the range of 0.1 to 120 hours. After the reaction is complete, the reaction mixture is neutralized with an acidic aqueous solution, extracted with an organic solvent, and the organic layer is dried, concentrated, and other post-treatment procedures are carried out to isolate compound (I-15). Compound (M7) is a commercially available compound, or can be prepared according to known methods.

[0032] Production Method L-1 The compound represented by formula (I-16) (hereinafter referred to as compound (I-16)) can be produced by a step (step M-1) of reacting compound (I-13) with a chlorinating agent to obtain a compound represented by formula (IM-17) (hereinafter referred to as compound (IM-17)), and a step (step M-2) of reacting compound (IM-17) obtained in step M-1 with a compound represented by formula (M8) (hereinafter referred to as compound (M8)) in the presence of a base to obtain compound (I-16). (wherein the symbols have the same meanings as defined above.)

[0033] First, step M-1 will be described. The reaction is typically carried out in a single solvent or a mixed solvent. Examples of solvents used in the reaction include hydrocarbons, ethers, halogenated hydrocarbons, esters, and mixtures of two or more of these. Examples of chlorinating agents used in the reaction include thionyl chloride, oxalyl chloride, and phosphorus oxychloride. Such chlorinating agents are typically used in a ratio of 1 to 10 moles per mole of compound (I-13). The reaction may be carried out in the presence of a catalyst. Examples of catalysts include DMF. When the reaction is carried out in the presence of a catalyst, the catalyst is typically used in a ratio of 0.01 to 1 mole per mole of compound (I-13). The reaction temperature is typically within the range of −80 to 150°C. The reaction time is typically within the range of 0.1 to 120 hours. After completion of the reaction, compound (IM-17) can be isolated by post-treatment. Alternatively, the reaction mixture after completion of the reaction may be directly subjected to step M-2, or a mixture obtained by concentrating the reaction mixture may be subjected to step M-2. Next, step M-2 will be described. The reaction is typically carried out in a single solvent or a mixed solvent. Examples of solvents used in the reaction include hydrocarbons; ethers; halogenated hydrocarbons; esters; and mixtures of two or more of these. Examples of bases used in the reaction include organic bases; alkaline earth metal carbonates; alkali metal carbonates; alkali metal hydrogencarbonates; metal carboxylates; and metal hydroxides. For the reaction, compound (M8) is typically used in a ratio of 1 to 10 moles and a base is typically used in a ratio of 0 to 10 moles per mole of compound (I-13) used in step M-1. The reaction temperature is typically within the range of −80 to 150°C. The reaction time is typically within the range of 0.1 to 120 hours. After completion of the reaction, compound (I-16) can be isolated by mixing the reaction mixture with water, extracting with an organic solvent, and performing post-treatments such as washing, drying, and concentrating the organic layer. The reaction conditions (solvent, reaction temperature, reaction time, etc.) in steps M-1 and M-2 may be the same or different.Steps M-1 and M-2 may be carried out simultaneously by mixing compound (I-13), a chlorinating agent, a base, and compound (M8), or step M-1 may be carried out first and then step M-2. Step M-2 may also be started between the start and end of step M-1.

[0034] Production Method L A compound represented by formula (I-18) (hereinafter referred to as compound (I-18)), a compound represented by formula (I-19) (hereinafter referred to as compound (I-19)), and a compound represented by formula (I-20) (hereinafter referred to as compound (I-20)) can be produced by reacting compound (I-11) with a sulfating agent. [In the formula, the symbols have the same meanings as defined above.] The reaction is usually carried out in a single solvent or a mixed solvent. Examples of solvents used in the reaction include hydrocarbons, ethers, halogenated hydrocarbons, and mixtures of two or more thereof. Examples of sulfurizing agents used in the reaction include diphosphorus pentasulfide and 2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane 2,4-disulfide (hereinafter referred to as Lawesson's reagent). The reaction may be carried out in the presence of a base. Examples of the base include organic bases, alkali metal carbonates, alkaline earth metal carbonates, alkali metal hydrogencarbonates, metal carboxylates, metal alkoxides, metal hydroxides, and metal hydrides. When the reaction is carried out in the presence of a base, the base is usually used in a ratio of 1 to 10 moles per mole of compound (I-16). In the reaction, the sulfurizing agent is usually used in a ratio of 1 to 10 moles per mole of compound (I-11). The reaction temperature is usually within the range of -20 to 150°C. The reaction time is usually within the range of 0.1 to 120 hours. After completion of the reaction, the reaction mixture is mixed with water, extracted with an organic solvent, and the organic layer is dried, concentrated, or other post-treatment procedures are carried out to isolate compound (I-18), compound (I-19), or compound (I-20). The proportions of compound (I-18), compound (I-19), and compound (I-20) produced can be increased or decreased by adjusting the type of solvent and sulfurizing agent, the equivalent amount of the sulfurizing agent, the reaction temperature, and the reaction time.

[0035] Production Method M Compound (I-21) can be produced by a step (Step M-3) of treating a compound represented by formula (I-22) (hereinafter referred to as compound (I-22)) with a halogenating agent or a sulfonylating agent to obtain a compound represented by formula (I-23) (hereinafter referred to as compound (I-23)), and a step (Step M-4) of reacting compound (I-23) obtained in Step M-3 with a compound represented by formula (M9) (hereinafter referred to as compound (M9)) in the presence of a base to obtain compound (I-21). [In the formula, L ３ represents a chlorine atom, a methanesulfonyloxy group, a trifluoromethylsulfonyloxy group, a 4-methylphenylsulfonyloxy group, or a phenylsulfonyloxy group; R １ａ is a group represented by formula (C-2) (wherein ● represents a bonding site with a carbon atom or a hydrogen atom, and G １１ａ , G １１ｂ , G １１ｃ , G １１ｄ are the same or different and each represents a nitrogen atom or G １ represents a methine group which may be substituted with one or more substituents selected from the following:

[0036] First, step M-3 will be described. The reaction is usually carried out in a single solvent or a mixed solvent. Examples of solvents used in the reaction include hydrocarbons, halogenated hydrocarbons, ethers, nitriles, and mixtures of two or more of these. Examples of chlorinating agents used in the reaction include thionyl chloride and phosphorus trichloride. Examples of sulfonylating agents used in the reaction include paratoluenesulfonyl chloride, methanesulfonyl chloride, paratoluenesulfonic anhydride, and methanesulfonic anhydride, and examples of bases include organic bases such as pyridine and triethylamine. In the reaction, the chlorinating agent or sulfonylating agent is usually used in a ratio of 1 to 10 moles and the base is usually used in a ratio of 0 to 10 moles per mole of compound (I-22). The reaction temperature is usually within the range of 0 to 150°C. The reaction time is usually within the range of 0.1 to 120 hours. After completion of the reaction, compound (I-23) can be isolated by mixing the reaction mixture with water, extracting with an organic solvent, drying and concentrating the organic layer, or by subjecting the residue to column chromatography or other post-treatment procedures.

[0037] Next, step M-4 will be described. The reaction is usually carried out in a single solvent or a mixed solvent. Examples of solvents used in the reaction include hydrocarbons; ethers; halogenated hydrocarbons; amides; esters; nitriles; imidazolinones; sulfoxides; and mixtures of two or more thereof. Examples of bases used in the reaction include organic bases; alkali metal carbonates; alkaline earth metal carbonates; metal hydroxides, metal hydrides, and the like. Such bases are usually used in a ratio of 1 to 10 moles per mole of compound (I-23). ​​The reaction may be carried out in the presence of a catalyst. Examples of catalysts include alkali metal halides such as sodium iodide, sodium bromide, lithium iodide, and lithium bromide; and ammonium salts such as tetrabutylammonium iodide and tetrabutylammonium bromide. When the reaction is carried out in the presence of a catalyst, the catalyst is usually used in a ratio of 0.01 to 1 mole per mole of compound (I-23). ​​The reaction temperature is usually within the range of −20 to 150° C. The reaction time is usually within the range of 0.1 to 120 hours. After completion of the reaction, compound (I-21) can be isolated by carrying out post-treatment.

[0038] Reference Production Method 1 Compound (A1) can be produced by reacting a compound represented by formula (A6) (hereinafter referred to as compound (A6)) in the presence of a halogenating agent. [In the formula, the symbols have the same meanings as defined above.] The reaction is usually carried out in a single solvent or a mixed solvent. Examples of solvents used in the reaction include hydrocarbons; ethers; halogenated hydrocarbons; amides; esters; nitriles; imidazolinones; sulfoxides; and mixtures of two or more thereof. Examples of halogenating agents used in the reaction include chlorine, bromine, iodine, N-chlorosuccinimide, N-bromosuccinimide, N-iodosuccinimide, 1,3-dibromo-5,5-dimethylhydantoin, and dibromoisocyanuric acid. The halogenating agent is usually used in a ratio of 1 to 10 moles per mole of compound (A6). The reaction temperature is usually within the range of −100 to 200°C. The reaction time is usually within the range of 0.1 to 120 hours. After completion of the reaction, compound (A1) can be isolated by post-treatment such as mixing the reaction mixture with water, extracting it with an organic solvent, and drying and concentrating the organic layer.

[0039] Reference Production Method 2 Compound (A6) can be produced by reacting a compound represented by formula (A7) (hereinafter referred to as compound (A7)) with compound (M6) in the presence of a base. [wherein the symbols have the same meanings as defined above.] The reaction can be carried out according to Production Method F, except that compound (A7) is used in place of compound (I-10).

[0040] Reference Production Method 3 Compound (A7) can be produced using compound (A2) and a compound represented by formula (A8) (hereinafter referred to as compound (A8)) according to the following scheme. [In the formula, the symbols have the same meanings as defined above.] Each reaction in the above scheme can be carried out according to Production Method G. Compound (A8) is a commercially available compound, or can be produced according to a known method.

[0041] Reference Production Method 4 Compound (A10) can be produced from a compound represented by formula (A12) (hereinafter referred to as compound (A12)) according to the scheme described below. [In the formula, the symbols have the same meanings as defined above.] Each reaction in the above scheme can be carried out in accordance with the method described in Organic Letters 2022, 24, 3440-3444. Compound (A12) can be produced in accordance with a known method. In addition, compound (A12) and a compound represented by formula (A12-1) (hereinafter referred to as compound (A12-1)) may exist as keto-enol tautomers. Compound (A12) and compound (A12-1) include each keto-enol tautomer and a mixture of keto-enol tautomers in any ratio.

[0042] Reference Production Method 5 Compound (A-13) can be produced by reacting a compound represented by formula (A1) (hereinafter referred to as compound (A1)) with a compound represented by formula (M10) (hereinafter referred to as compound (M10)) in the presence of a base and a catalyst, according to the scheme described below. [In the formula, R 6arepresents a C1-C6 alkyl group, a C1-C6 alkoxy group, or a phenyl group, and other symbols have the same meanings as above.] The reaction is usually carried out in a single solvent or a mixed solvent. Solvents used in the reaction include hydrocarbons, ethers, halogenated hydrocarbons, amides, esters, nitriles, water, and mixtures of two or more thereof. Catalysts used in the reaction include palladium catalysts such as tetrakistriphenylphosphinepalladium(0), palladium(II) acetate, tris(dibenzylideneacetone)dipalladium, and [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride. Bases used in the reaction include organic bases, alkali metal carbonates, alkali metal hydrogencarbonates, alkaline earth metal carbonates, sodium fluoride, and tripotassium phosphate. In the reaction, compound (M10) is usually used in a ratio of 1 to 10 moles, the catalyst is usually used in a ratio of 0.01 to 1 mole, and the base is usually used in a ratio of 1 to 10 moles, relative to 1 mole of compound (A1). The reaction temperature is usually within the range of 0 to 150°C. The reaction time is usually within the range of 0.1 to 120 hours. After completion of the reaction, compound (A-13) can be isolated by performing post-treatment operations such as mixing the reaction mixture with water, extracting with an organic solvent, and drying and concentrating the organic layer.

[0043] Compound (I-22) can be produced by reacting compound (A-13) with an oxidizing agent and then with a reducing agent according to the scheme described below. [In the formula, the symbols have the same meanings as above.] The reaction is usually carried out in a single solvent or a mixed solvent. Examples of solvents used in the reaction include hydrocarbons, halogenated hydrocarbons, esters, alcohols, nitriles, water, and mixtures of two or more thereof. Examples of oxidizing agents used in the reaction include ozone, osmium tetroxide, sodium periodate, potassium periodate, ruthenium (IV) oxide, and ruthenium chloride. Examples of reducing agents used in the reaction include borohydride salts such as sodium borohydride and potassium borohydride. The oxidizing agent is usually used in an amount of 1 mole to an excess amount per mole of compound (A-13). When ozone is used as the oxidizing agent, a large excess of ozone is used per mole of compound (A-13). The reducing agent is usually used in a ratio of 0.3 to 1.5 moles per mole of compound (A-13). The reaction temperature is usually within the range of -80 to 200°C. The reaction time is usually within the range of 0.1 to 120 hours. After completion of the reaction, the reaction mixture is mixed with water, followed by extraction with an organic solvent, and the organic layer is dried and concentrated, or the residue is subjected to column chromatography or other post-treatment procedures to isolate compound (I-22).

[0044] The compound of the present invention can be mixed or used in combination with one or more components selected from the group consisting of Group (a), Group (b), Group (c), Group (d), Group (e), and Group (f) below (hereinafter referred to as the present component). The term "mixed or used in combination" means that the compound of the present invention and the present component are used simultaneously, separately, or with a time interval between them. When the compound of the present invention and the present component are used simultaneously, the compound of the present invention and the present component may be contained in separate preparations or in a single preparation. One aspect of the present invention is a composition (hereinafter referred to as Composition A) containing one or more components selected from the group consisting of Group (d) and Group (f) (i.e., the present component) and the compound of the present invention.

[0045] Group (a) includes acetylcholinesterase inhibitors (e.g., carbamate insecticides, organophosphate insecticides), GABAergic chloride channel blockers (e.g., phenylpyrazole insecticides), sodium channel modulators (e.g., pyrethroid insecticides), nicotinic acetylcholine receptor competitive modulators (e.g., neonicotinoid insecticides), nicotinic acetylcholine receptor allosteric modulators, glutamate-gated chloride channel allosteric modulators (e.g., macrolide insecticides), juvenile hormone mimics, multisite inhibitors, chordotonal organ TRPV channel modulators, mite growth inhibitors, microbial insect midgut membrane disruptors, mitochondrial ATP synthase inhibitors, oxidative phosphorylation uncouplers, nicotinic acetylcholine receptor channel blockers (e.g., nereistoxin insecticides), chitin biosynthesis inhibitors, molting inhibitors, ecdysone receptor agonists, octopamine receptor agonists, mitochondrial electron transport chain complexes I and II, The group consisting of inhibitors of classes III and IV, voltage-dependent sodium channel blockers, acetyl-CoA carboxylase inhibitors, ryanodine receptor modulators (e.g., diamide insecticides), chordotonal organ modulators, microbial insecticides, and other insecticidal, acaricidal, and nematicidal active ingredients, which are described in the IRAC mechanism-based classification.

[0046] Group (b) consists of nucleic acid synthesis inhibitors (e.g., phenylamide fungicides, acylamino acid fungicides), cell division and cytoskeleton inhibitors (e.g., MBC fungicides), respiratory inhibitors (e.g., QoI fungicides, QiI fungicides), amino acid synthesis and protein synthesis inhibitors (e.g., anilinopyridine fungicides), signal transduction inhibitors, lipid synthesis and membrane synthesis inhibitors, sterol biosynthesis inhibitors (e.g., DMI fungicides such as triazoles), cell wall biosynthesis inhibitors, melanin synthesis inhibitors, plant defense inducers, multisite contact-active fungicides, microbial fungicides, and other fungicidal active ingredients. These are listed in the FRAC classification based on the mechanism of action.

[0047] Group (c) is a group of plant growth regulators (including mycorrhizal fungi and rhizobia).

[0048] Group (d) is a group of safening ingredients.

[0049] Group (e) is a group of synergists that enhance the efficacy of other drugs when used in combination with them.

[0050] Group (f) consists of acetyl-CoA carboxylase (ACCase) inhibitors, acetolactate synthase (ALS) inhibitors, photosynthesis (photosystem II) inhibitors, photosystem I electron converters, protoporphyrinogen oxidase (PPO) inhibitors, phytoene desaturase system (PDS) inhibitors, 4-hydroxyphenylpyruvate dioxygenase (4-HPPD) inhibitors, carotenoid biosynthesis inhibitors, EPSP synthase inhibitors, glutamine synthase inhibitors, dihydropteroic acid (DHP) synthase inhibitors, microtubule polymerization inhibitors, mitosis / microtubule formation inhibitors, very long-chain fatty acid (VLCFA) inhibitors, cellulose synthesis inhibitors, uncoupling agents, lipid synthesis inhibitors, indoleacetic acid-like active agents, auxin transport inhibitors, and other herbicidal active ingredients. These are listed in the HRAC classification based on the mechanism of action.

[0051] Examples of combinations of the present component and the compound of the present invention are described below. For example, alanycarb + SX refers to a combination of alanycarb and SX. The abbreviation SX refers to any one of the present compounds selected from the compound groups SX1 to SX24 and present compounds 1 to 236. The present components described below are all known and can be obtained from commercially available preparations or produced by known methods. When the present component is a microorganism, it can also be obtained from a bacterial depository. The number in parentheses indicates the CAS RN (registered trademark).

[0052] Combinations of the present ingredient of the above group (a) with the compound of the present invention: abamectin + SX, acephate + SX, acequinocyl + SX, acetamiprid + SX, acetoprole + SX, acrinathrin + SX, acinonapyr + SX, afidopyropen + SX, afoxolaner + SX, alanycarb + SX, aldicarb + SX, allethrin + SX, alpha-cypermethrin + SX, alpha-endosulfan + SX, aluminum phosphide + SX, Amitraz + SX, azadirachtin + SX, azamethiphos + SX, azinphos-ethyl + SX, azinphos-methyl + SX, azocyclotin + SX, Celastrus angulatus bark + SX, bendiocarb + SX, benfluthrin + SX, benfuracarb + SX, bensultap + SX, bentiofluorin + SX, benzoximate + SX, benzpyrimoxan + SX, beta-cyfluthrin + SX SX, beta-cypermethrin + SX, bifenazate + SX, bifenthrin + SX,Bioallethrin + SX, bioresmethrin + SX, bistrifluron + SX, bisulfufen + SX, borax + SX, boric acid + SX, broflanilide + SX, bromopropylate + SX, buprofezin + SX, butocarboxim + SX, butoxycarboxim + SX, cadusafos + SX, calcium phosphide + SX, carbaryl + SX, carbofuran + SX, carbosulfan + SX, Cartap hydrochloride + SX, cartap + SX, chinomethionate + SX, chlorantraniliprole + SX, chlordane + SX, chlorethoxyfos + SX, chlorfenapyr + SX, chlorfenvinphos + SX, chlorfluazuron + SX, chlormephos + SX, chloropicrin + SX, chlorpyrifos + SX, chlorpyrifos-methyl + SX, chromafenozide + SX, clofentezine + SX, clothianidin + SX, concanamycin A + SX, coumaphos + SX, cryolite + SX,Cyanophos + SX, cyantraniliprole + SX, cybenzoxasulfyl + SX, cyclaniliprole + SX, cyclobutrifluram + SX, cycloprothrin + SX, cycloxaprid + SX, cyenopyrafen + SX, cyetpyrafen + SX, cyflumetofen + SX, cyfluthrin + SX, cyhalodiamide + SX, cyhalothrin + SX, cyhexatin + SX, cypermethrin + SX, Cyphenothrin + SX, cyproflanilide + SX, cyromazine + SX, dazomet + SX, deltamethrin + SX, demeton-S-methyl + SX, diafenthiuron + SX, diazinon + SX, dichlorvos + SX, dichloromezotiaz + SX, dicofol + SX, dicrotophos + SX, diflovidazin + SX, diflubenzuron + SX, dimefluthrin + SX, Dimethoate + SX, dimethylvinphos + SX, dimpropyridaz + SX, dinotefuran + SX, disodium octaborate + SX,Disulfoton + SX, DNOC (2-methyl-4,6-dinitrophenol) + SX, doramectin + SX, dried leaves of Dryopteris filix (mas) + SX, emamectin benzoate + SX, empenthrin + SX, endosulfan + SX, EPN (O-ethyl O-(4-nitrophenyl) phenylphosphonothioate) + SX, epsilon-metofluthrin + SX, epsilon-momfluorothrin + SX, esfenvalerate + SX, ethiofencarb + SX, ethion + SX, Ethiprole + SX, ethoprophos + SX, etofenprox + SX, etoxazole + SX, Artemisia absinthium extract + SX, Azadirachta indica extract + SX, Cassia nigricans extract + SX, Clitoria ternatea extract + SX, Symphytum officinale extract + SX, Chenopodium ambrosioides extract + SX, Tansy extract + SX, Urtica dioica extract + SX, Mistletoe extract (extract of Viscum album) + SX,Famphur + SX, fenamiphos + SX, fenazaquin + SX, fenbutatin oxide + SX, fenitrothion + SX, fenmezoditiaz + SX, fenobucarb + SX, fenoxycarb + SX, fenpropathrin + SX, fenpyroximate + SX, fenthion + SX, fenvalerate + SX, fipronil + SX, flometoquin + SX, flonicamid + SX, Fluacrypyrim + SX, Fluazaindolizine + SX, Fluazuron + SX, Flubendiamide + SX, Fluchlordiniliprole + SX, Flucycloxuron + SX, Flucythrinate + SX, Fluensulfone + SX, Flufenoprox + SX, Flufenoxuron + SX, Flufiprole + SX, Flumethrin + SX, Flumetnicam + SX, Flupentiofenox + SX Flupyradifurone + SX, flupyrimin + SX, flupyroxystrobin + SX, fluralaner + SX, fluvalinate + SX,Fluxametamide + SX, formetanate + SX, fosthiazate + SX, furamethrin + SX, furathiocarb + SX, gamma-cyhalothrin + SX, GS-omega / kappa HXTX-Hv1a peptide + SX, halfenprox + SX, halofenozide + SX, heptafluthrin + SX, heptenophos + SX, hexaflumuron + SX, hexythiazox + SX, Potassium salt of hop beta acid + SX, hydramethylnon + SX, hydroprene + SX, imicyafos + SX, imidacloprid + SX, imidaclothiz + SX, imiprothrin + SX, indazapyroxamet + SX, indoxacarb + SX, isocycloseram + SX, isofenphos + SX, isoflualanam + SX, isoprocarb + SX, isopropyl-O-(methoxyaminothiophosphoryl) salicylate salicylate + SX, isoxathion + SX, ivermectin + SX, kadethrin + SX, kappa-tefluthrin + SX,Kappa-bifenthrin + SX, kinoprene + SX, lambda-cyhalothrin + SX, ledprona + SX, lenoremycin + SX, lepimectin + SX, lime sulfur + SX, lotilaner + SX, lufenuron + SX, machine oil + SX, malathion + SX, mecarbam + SX, meperfluthrin + SX, metaflumizone + SX, metam + SX, methamidophos + SX, Methidathion + SX, methiocarb + SX, methomyl + SX, methoprene + SX, methoxychlor + SX, methoxyfenozide + SX, methyl bromide + SX, metofluthrin + SX, metolcarb + SX, metoxadiazone + SX, mevinphos + SX, milbemectin + SX, milbemycin oxime + SX, mivorilaner + SX, modoflaner + SX, momfluorothrin + SX Monocrotophos + SX, moxidectin + SX, naled + SX, nicofluprole + SX, nicotine + SX,Nicotine sulfate + SX, nitenpyram + SX, novaluron + SX, noviflumuron + SX, Chenopodium anthelminticum seed oil + SX, omethoate + SX, oxamyl + SX, oxazosulfyl + SX, oxydemeton-methyl + SX, parathion + SX, parathion-methyl + SX, permethrin + SX, phenothrin + SX, phenthoate + SX, phorate + SX, phosalone + SX, phosmet + SX, phosphamidon + SX, phosphine + SX, phoxim + SX, pioxaniliprole + SX, piperflanilide + SX, pirimicarb + SX, pirimiphos-methyl + SX, prallethrin + SX, profenofos + SX, profluthrin + SX, propargite + SX, propetamphos + SX, propoxur + SX, propylene glycol alginate + SX, prothiofos + SX, Piflubumide + SX, pymetrozine + SX, pyraclofos + SX,Pyrethrins + SX, pyridaben + SX, pyridalyl + SX, pyridaphenthion + SX, pyrifluquinazone + SX, pyrimidifen + SX, pyriminostrobin + SX, pyriprole + SX, pyriproxyfen + SX, quinalphos + SX, resmethrin + SX, rotenone + SX, ryanodine + SX, sarolaner + SX, selamectin + SX, sigma-cypermethrin + SX, silafluofen + SX, sodium borate + SX, sodium metaborate + SX, spidoxamat + SX, spinetoram + SX, spinosad + SX, spirobudifen + SX, spirodiclofen + SX, spiromesifen + SX, spiropidione + SX, spirotetramat + SX, sulfiflumin + SX, sulfluramid + SX, sulfotep + SX, sulfoxaflor + SX, sulfoxamyl + SX, sulfur + SX, sulfuryl fluoride + SX, tartar emetic + SX, tau-fluvalinate + SX,Tebufenozide + SX, tebufenpyrad + SX, tebupirimfos + SX, teflubenzuron + SX, tefluthrin + SX, temephos + SX, terbufos + SX, terpene constituents of the extract of Chenopodium ambrosioides near ambrosioides + SX, tetrachlorantraniliprole + SX, tetrachlorvinphos + SX, tetradifon + SX, tetramethrin + SX, tetramethylfluthrin + SX, Tetraniliprole + SX, theta-cypermethrin + SX, thiacloprid + SX, thiamethoxam + SX, thiocyclam + SX, thiodicarb + SX, thiofanox + SX, thiometon + SX, thiosultap disodium + SX, thiosultap monosodium + SX, thiapyrachlor + SX, tigolaner + SX, thioantraniliprole + SX, tioxazafen + SX, Tolfenpyrad + SX, tralomethrin + SX, transfluthrin + SX,Triazamate + SX, triazophos + SX, trichlorfon + SX, trifluenfuronate + SX, triflumezopyrim + SX, triflumuron + SX, trimethacarb + SX, trioxyflanilide + SX, tyclopyrazoflor + SX, umifoxolaner + SX, vadescana + SX, vamidothion + SX, vinylfluthrin + SX, Quassia amara wood extract + SX, XMC (3,5-dimethylphenyl N-methylcarbamate + SX, xylylcarb + SX, zeta-cypermethrin + SX, zinc phosphide + SX, 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-methyl-N-(1-oxothietan-3-yl)benzamide (1241050-20-3) + SX, 3-methoxy-N-(5-{5-(trifluoromethyl)-5-[3-(trifluoromethyl)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}indan-1-yl)propanamide (1118626-57-5) + SX, N-{4-chloro-3-[(1-cyanocyclopropyl)carbamoyl]phenyl}-1-methyl-4-(methanesulfonyl)-3-(1,1,2,2,2-pentafluoroethyl)-1H-pyrazole-3-carboxamide (1400768-21-9) + SX,N-[3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl]-2-(methanesulfonyl)propanamide (2396747-83-2) + SX, N-[4-chloro-2-(pyridin-3-yl)-1,3-thiazol-5-yl]-N-ethyl-3-(methanesulfonyl)propanamide + SX, 1,4-dimethyl-2-[2-(pyridin-3-yl)-2H-indazol-5-yl]-1,2,4-triazolidine-3,5-dione (2171099-09-3) + SX, 2-isopropyl-5-[(3,4,4-trifluoro-3-buten-1-yl)sulfonyl]-1,3,4-thiadiazole (2058052-95-0) + SX, N-({2-fluoro-4-[(2S,3S)-2-hydroxy-3-(3,4,5-trichlorophenyl)-3-(trifluoromethyl)pyrrolidin-1-yl]phenyl}methyl)cyclopropanecarboxamide + SX, 7-fluoro-N-[1-(methylsulfanyl)-2-methylpropan-2-yl]-2-(pyridin-3-yl)-2H-indazole-4-carboxamide + SX, 7-fluoro-N-[1-(methanesulfinyl)-2-methylpropan-2-yl]-2-(pyridin-3-yl)-2H-indazole-4-carboxamide + SX, 7-fluoro-N-[1-(methanesulfonyl)-2-methylpropan-2-yl]-2-(pyridin-3-yl)-2H-indazole-4-carboxamide + SX, N-[1-(difluoromethyl)cyclopropyl]-2-(pyridin-3-yl)-2H-indazole-4-carboxamide + SX, 2,9-dihydro-9-(methoxymethyl)-2-(pyridin-3-yl)-10H-pyrazolo[3,4-f]pyrido[2,3-b][1,4]oxazepin-10-one (2607927-97-7) + SX, (S)-2-chloro-N-(3-ethylpentan-2-yl)furan-3-carboxamide + SX, Cry1Ab protein from Bacillus thuringiensis (Bacillus thuringiensis Cry1Ab protein) + SX, Cry1Ac protein from Bacillus thuringiensis (Bacillus thuringiensis Cry1Ac protein) + SX, Cry1Fa protein from Bacillus thuringiensis (Bacillus thuringiensis Cry1Fa protein) + SX, Cry1A.105 protein from Bacillus thuringiensis (Bacillus thuringiensis Cry1A.105 protein) + SX, Cry2Ab protein from Bacillus thuringiensis (Bacillus thuringiensis Cry2Ab protein) protein) + SX, Bacillus thuringiensis-derived Vip3A protein (Bacillus thuringiensis Vip3A protein) + SX, Bacillus thuringiensis-derived mCry3A protein (Bacillus thuringiensis mCry3A protein) + SX, Bacillus thuringiensis-derived Cry3Ab protein (Bacillus thuringiensis Cry3Ab protein) + SX, Bacillus thuringiensis-derived Cry3Bb protein (Bacillus thuringiensis Cry3Bb protein) + SX, Bacillus thuringiensis-derived Cry34Ab1 / Cry35Ab1 protein (Bacillus thuringiensis Cry34Ab1 / Cry35Ab1 protein) + SX,Adoxophyes orana granulovirus BV-0001 (GV strain BV-0001) + SX, Anticarsia gemmatalis multiple nucleocapsid nucleopolyhedrovirus (MNPV) + SX, Autographa californica MNPV + SX, Cydia pomonella granulosis virus V15 (GV strain V15) + SX, Cydia pomonella granulosis virus V22 (GV strain V22) + SX, Cryptophlebia leucotreta granulosis virus (GV) + SX, Dendrolimus punctatus cypovirus + SX, Helicoverpa armigera nucleopolyhedrovirus BV-0003 + SX, Helicoverpa zea nucleopolyhedrovirus (NPV) + SX, Lymantria dispar nucleopolyhedrovirus (NPV) + SX, Mamestra brassicae nucleopolyhedrovirus (NPV) + SX, Mamestra configurata nucleopolyhedrovirus (NPV) + SX, Neodiprion abietis nucleopolyhedrovirus (NPV) + SX, Neodiprion lecontei NPV + SX, Neodiprion sertifer NPV + SX, Nosema locustae + SX,Orgyia pseudotsugata nucleopolyhedrovirus (NPV) + SX, Pieris rapae granulosis virus (GV) + SX, Plodia interpunctella granulosis virus (GV) + SX, Spodoptera exigua nucleopolyhedrovirus (MNPV) + SX, Spodoptera littoralis nucleopolyhedrovirus (MNPV) + SX, Spodoptera litura nucleopolyhedrovirus (NPV) + SX, Arthrobotrys dactyloides + SX, Bacillus firmus strain GB-126 + SX, Bacillus firmus strain I-1582 + SX, Bacillus firmus strain NCIM2637 + SX SX, Bacillus megaterium + SX, Bacillus sp. strain AQ175 + SX, Bacillus sp. strain AQ177 + SX, Bacillus sp. strain AQ178 + SX, Bacillus sphaericus strain 2362 serotype H5a5b + SX, Bacillus sphaericus strain ABTS1743 + SX, Bacillus thuringiensis strain AQ52 + SX, Bacillus thuringiensis strain BD#32 + SX, Bacillus thuringiensis strain CR-371 + SX, Bacillus thuringiensis subsp. Aizawai strain ABTS-1857 + SX, Bacillus thuringiensis subsp. Aizawai strain AM65-52 + SX, Bacillus thuringiensis subsp. Aizawai strain GC-91 + SX,Bacillus thuringiensis subsp. Aizawai strain NB200 + SX, Bacillus thuringiensis subsp. Aizawai Serotype strain H-7 + SX, Bacillus thuringiensis subsp. Kurstaki strain ABTS351 + SX, Bacillus thuringiensis subsp. Kurstaki strain BMP123 + SX, Bacillus thuringiensis subsp. Kurstaki strain CCT1306 + SX, Bacillus thuringiensis subsp. Kurstaki strain EG2348 + SX, Bacillus thuringiensis subsp. Kurstaki strain EG7841 + SX, Bacillus thuringiensis subsp. Kurstaki strain EVB113-19 + SX, Bacillus thuringiensis subsp. Kurstaki strain F810 + SX, Bacillus thuringiensis subsp. Kurstaki strain HD-1 + SX, Bacillus thuringiensis subsp. Kurstaki strain PB54 + SX, Bacillus thuringiensis subsp. Kurstaki strain SA-11 + SX, Bacillus thuringiensis subsp. Kurstaki strain SA-12 + SX, Bacillus thuringiensis subsp. Tenebriosis strain NB176 + SX, Bacillus thuringiensis subsp. Thuringiensis strain MPPL002 + SX, Bacillus thuringiensis subsp. morrisoni + SX, Bacillus thuringiensis var. colmeri + SX,Bacillus thuringiensis var. darmstadiensis strain 24-91 + SX, Bacillus thuringiensis var. dendrolimus + SX, Bacillus thuringiensis var. galleriae + SX, Bacillus thuringiensis var. israelensis strain BMP144 + SX, Bacillus thuringiensis var. israelensis serotype strain H-14 + SX, Bacillus thuringiensis var. japonensis strain buibui + SX, Bacillus thuringiensis var. san diego strain M-7 + SX, Bacillus thuringiensis var. 7216 + SX, Bacillus thuringiensis var. aegypti + SX, Bacillus thuringiensis var. T36 + SX, Beauveria bassiana strain ANT-03 + SX, Beauveria bassiana strain ATCC74040 + SX, Beauveria bassiana strain GHA + SX, Beauveria brongniartii + SX, Burkholderia rinogensis strain A396 + SX, Chromobacterium subtsugae strain PRAA4-1T + SX, Dactyllela ellipsospora + SX, Dactylaria thaumasia + SX, Hirsutella minnesotensis + SX, Hirsutella rhossiliensis + SX, Hirsutella thompsonii + SX, Lagenidium giganteum + SX, Lecanicillium lecanii strain KV01 + SX,Lecanicillium lecanii conidia of strain DAOM198499 + SX, Lecanicillium lecanii conidia of strain DAOM216596 + SX, Lecanicillium muscarium strain Ve6 + SX, Metarhizium anisopliae strain F52 + SX, Metarhizium anisopliae var. acridum + SX, Metarhizium anisopliae var. anisopliae BIPESCO 5 / F52 + SX, Metarhizium flavoviride + SX, Monacrosporium phymatopagum + SX, Paecilomyces fumosoroseus Apopka strain 97 + SX, Paecilomyces lilacinus strain 251 + SX, Paecilomyces tenuipes strain T1 + SX, Paenibacillus popilliae + SX, Pasteuria nishizawae strain Pn1 + SX, Pasteuria penetrans + SX, Pasteuria usgae + SX, Pasteuria thornei + SX, Serratia entomophila + SX, Verticillium chlamydosporium + SX, Verticillium lecani strain NCIM1312 + SX, Wolbachia pipientis + SX。,

[0053] Combinations of the present ingredient of the above group (b) with the compound of the present invention: acibenzolar-S-methyl + SX, aldimorph + SX, ametoctradin + SX, aminopyrifen + SX, aminotipyr + SX, amisulbrom + SX, anilazine + SX, azaconazole + SX, azoxystrobin + SX, basic copper sulfate + SX, benalaxyl + SX, benalaxyl-M + SX, benodanil + SX, benomyl + SX, benthiavalicarb + SX, benthiavalicarb-isopropyl + SX, benzovindiflupyr + SX, bifemetstrobin + SX, binapacryl + SX, biphenyl + SX, bitertanol + SX, bixafen + SX, blasticidin S + SX, Bordeaux mixture + SX, boscalid + SX, bromothalonil + SX, bromuconazole + SX, bupirimate + SX, captafol + SX, captan + SX, Carbendazim + SX, carboxin + SX, carpropamid + SX, chinomethionate + SX, chitin + SX,Chlorinconazide + SX, chloroneb + ​​SX, chlorothalonil + SX, chlozolinate + SX, colletochlorin B + SX, copper(II) acetate + SX, copper(II) hydroxide + SX, copper oxychloride + SX, copper(II) sulfate + SX, coumoxystrobin + SX, cyazofamid + SX, cyflufenamid + SX, cymoxanil + SX, cyproconazole + SX, Cyprodinil + SX, dichlobentiazox + SX, dichlofluanid + SX, diclocymet + SX, diclomezine + SX, dicloran + SX, diethofencarb + SX, difenoconazole + SX, diflumetorim + SX, dimethachlone + SX, dimethirimol + SX, dimethomorph + SX, dimoxystrobin + SX, diniconazole + SX, diniconazole-M + SX SX, dinocap + SX, dipotassium hydrogenphosphite + SX, dipymetitrone + SX, dithianon + SX,Dodecylbenzenesulphonic acid bisethylenediamine copper(II) salt + SX, dodemorph + SX, dodine + SX, edifenphos + SX, enoxastrobin + SX, epoxiconazole + SX, etaconazole + SX, ethaboxam + SX, ethirimol + SX, etridiazole + SX, garlic extract (Allium sativum) + SX, extract of the cotyledons of lupine plantlets (BLAD) + SX, horsetail extract (Equisetum arvense) + SX SX, tea tree extract (Melaleuca alternifolia) + SX, giant knotweed extract (Reynoutria sachalinensis) + SX, nasturtium extract (Tropaeolus majus) + SX, famoxadone + SX, fenamidone + SX, fenaminstrobin + SX, fenarimol + SX, fenbuconazole + SX, feneptamidoquin + SX, fenfuram + SX, fenhexamid + SX, fenopyramide + SX, fenoxanil + SX Fenpiclonil + SX, fenpicoxamid + SX,Fenpropidin + SX, fenpropimorph + SX, fenpyrazamine + SX, triphenyltin acetate + SX, triphenyltin chloride + SX, fentin hydroxide + SX, ferbam + SX, ferimzone + SX, florylpicoxamid + SX, fluazinam + SX, flubeneteram + SX, fludioxonil + SX, flufenoxadiazam + SX, flufenoxystrobin + SX, fluindapyr + SX, flumetylsulforim + SX, flumorph + SX, fluopicolide + SX, fluopyram + SX, fluopimomide + SX, fluoroimide + SX, fluoxapiprolin + SX, fluoxastrobin + SX, fluoxytioconazole + SX, fluquinconazole + SX, fluquinometoate + SX, flusilazole + SX, flusulfamide + SX, flutianil + SX, flutolanil + SX, Flutriafol + SX, fluxapyroxad + SX, folpet + SX, fosetyl + SX,Fosetyl aluminum + SX, fuberidazole + SX, furalaxyl + SX, furametpyr + SX, galquin + SX, guazatine + SX, hexaconazole + SX, hymexazole + SX, imazalil + SX, imibenconazole + SX, iminoctadine + SX, iminoctadine triacetate + SX, inpyrfluxam + SX, iodocarb + SX, ipconazole + SX Ipfentrifluconazole + SX, ipflufenoquin + SX, iprobenfos + SX, iprodione + SX, iprovalicarb + SX, isofetamide + SX, isofleucine + SX, isoflucipram + SX, isoprothiolane + SX, isopyrazam + SX, isotianil + SX, kasugamycin + SX, kresoxim-methyl + SX, laminarin + SX, oak leaves and bark of quercus + SX, mancozeb + SX, Mandestrobin + SX, mandipropamid + SX, maneb + ​​SX, mefentrifluconazole + SX, mepanipyrim + SX,Mepronil + SX, meptyldinocap + SX, metalaxyl + SX, metalaxyl-M + SX, metarylpicoxamid + SX, metconazole + SX, metcyclofenstrobin + SX, methasulfocarb + SX, metiram + SX, metominostrobin + SX, metrafenone + SX, metyltetraprole + SX, myclobutanil + SX, naftifine + SX, nuarimol + SX, Octilinone + SX, ofurace + SX, orysastrobin + SX, oxadixyl + SX, oxathiapiprolin + SX, oxine-copper + SX, oxolinic acid + SX, oxpoconazole + SX, oxpoconazole fumarate + SX, oxycarboxin + SX, oxytetracycline + SX, pefurazoate + SX, penconazole + SX, pencycuron + SX, penflufen + SX, Penthiopyrad + SX, phenamacril + SX, phosphorous acid + SX, phthalide + SX, picarbutrazox + SX,Picoxystrobin + SX, piperalin + SX, polyoxins + SX, potassium hydrogencarbonate + SX, potassium dihydrogenphosphite + SX, probenazole + SX, prochloraz + SX, procymidone + SX, propamidine + SX, propamocarb + SX, propiconazole + SX, propineb + ​​SX, proquinazid + SX, prothiocarb + SX, prothioconazole + SX, pydiflumetofen + SX, Pyraclostrobin + SX, pyrametostrobin + SX, pyraoxystrobin + SX, pyrapropoyne + SX, pyraziflumid + SX, pyrazophos + SX, pyribencarb + SX, pyributicarb + SX, pyridaclomethyl + SX, pyrifenox + SX, pyrimethanil + SX, pyrimorph + SX, pyriophenone + SX, pyrisoxazole + SX, pyroquilon + SX Quillaja extract + SX, quinaminoprole + SX, quinconazole + SX,Quinofumelin + SX, quinoxyfen + SX, quintozene + SX, saponins of Chenopodium quinoa + SX, seboctylamine + SX, sedaxane + SX, silthiofam + SX, simeconazole + SX, sodium hydrogencarbonate + SX, spiroxamine + SX, streptomycin + SX, sulfur + SX, tebuconazole + SX, tebufloquin + SX, teclofthalam + SX Tecnazene + SX, terbinafine + SX, tetraconazole + SX, thiabendazole + SX, thifluzamide + SX, thiophanate + SX, thiophanate-methyl + SX, thiram + SX, thymol + SX, tiadinil + SX, tolclofos-methyl + SX, tolfenpyrad + SX, tolprocarb + SX, tolylfluanid + SX, triadimefon + SX, triadimenol + SX, Triazoxide + SX, triclopyricarb + SX, tricyclazole + SX, tridemorph + SX,Trifloxystrobin + SX, triflumizole + SX, triforine + SX, triticonazole + SX, validamycin + SX, valifenalate + SX, vinclozolin + SX, yellow mustard powder + SX, zinc thiazole + SX, zineb + ​​SX, ziram + SX, zoxamide + SX, N'-[4-({3-[(4-chlorophenyl)methyl]-1,2,4-thiadiazol-5-yl}oxy)-2,5-dimethylphenyl]-N-ethyl-N-methylmethanimidamide (1202781-91-6) + SX, N'-{4-[(4,5-dichlorothiazol-2-yl)oxy]-2,5-dimethylphenyl}-N-ethyl-N-methylmethanimidamide (929908-57-6) + SX, N'-(2,5-dimethyl-4-phenoxyphenyl)-N-ethyl-N-methylmethanimidamide (1052688-31-9) + SX, N'-[5-chloro-4-(2-fluorophenoxy)-2-methylphenyl]-N-ethyl-N-methylmethanimidamide (2055589-28-9) + SX, N'-[2-chloro-4-(2-fluorophenoxy)-5-methylphenyl]-N-ethyl-N-methylmethanimidamide (2055756-21-1) + SX, N'-(2-chloro-4-phenoxy-5-methylphenyl)-N-ethyl-N-methylmethanimidamide (2062599-39-5) + SX, N'-[4-(1-hydroxy-1-phenyl-2,2,2-trifluoroethyl)-2-methyl-5-methoxyphenyl]-N-isopropyl-N-methylmethanimidamide (2101814-55-3) + SX, N'-[5-bromo-6-(1-methyl-2-propoxyethoxy)-2-methylpyridin-3-yl]-N-ethyl-N-methylmethanimidamide (1817828-69-5) + SX, [4-(difluoromethoxy)phenyl]methyl 4-[(N-ethyl-N-methylamino)methylidene]amino-2,5-dimethylbenzoate + SX, 4-(2-bromo-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine (1362477-26-6) + SX, 2-[6-(3-fluoro-4-methoxyphenyl)-5-methylpyridin-2-yl]quinazoline (1257056-97-5) + SX, ethyl (2Z)-3-amino-2-cyano-3-phenylacrylate (39491-78-6) + SX, N-[(2-chlorothiazol-5-yl)methyl]-N-ethyl-6-methoxy-3-nitropyridin-2-amine (1446247-98-8) + SX, 5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1394057-11-4) + SX, (1R, 2S, 5S)-5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1801930-06-2) + SX, (1S, 2R, 5R)-5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1801930-07-3) + SX, 2-(chloromethyl)-5-(4-fluorobenzyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1394057-13-6) + SX, (1R, 2S, 5S)-2-(chloromethyl)-5-(4-fluorobenzyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1801930-08-4) + SX, (1S, 2R, 5R)-2-(chloromethyl)-5-(4-fluorobenzyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1801930-09-5) + SX, methyl 3-[(4-chlorophenyl)methyl]-2-hydroxy-1-methyl-2-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-carboxylate (1791398-02-1) + SX, 1-(2,4-difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)-1-[1-(4-bromo-2,6-difluorophenoxy)cyclopropyl]ethanol (2019215-86-0) + SX, 1-(2,4-difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)-1-[1-(4-chloro-2,6-difluorophenoxy)cyclopropyl]ethanol (2019215-84-8) + SX, 1-[2-(1-chlorocyclopropyl)-3-(2-fluorophenyl)-2-hydroxypropyl]-1H-imidazole-5-carbonitrile (2018316-13-5) + SX, 1-[2-(1-chlorocyclopropyl)-3-(2,3-difluorophenyl)-2-hydroxypropyl]-1H-imidazole-5-carbonitrile (2018317-25-2) + SX, 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)pyridin-3-yl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol (2082661-43-4) + SX, 2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)pyridin-3-yl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol (2082660-27-1) + SX, methyl ({2-methyl-5-[1-(4-methoxy-2-methylphenyl)-1H-pyrazol-3-yl]phenyl}methyl)carbamate (1605879-98-8) + SX, 2-(difluoromethyl)-N-[1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]pyridine-3-carboxamide (1616239-21-4) + SX, 2-(difluoromethyl)-N-[3-ethyl-1,1-dimethyl-2,3-dihydro-1H-inden-4-yl]pyridine-3-carboxamide (1847460-02-9) + SX, 2-(difluoromethyl)-N-[3-propyl-1,1-dimethyl-2,3-dihydro-1H-inden-4-yl]pyridine-3-carboxamide (1847460-05-2) + SX, (2E,3Z)-5-{[1-(4-chlorophenyl)-1H-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3-enamide (1445331-27-0) + SX, (2E,3Z)-5-{[1-(2,4-dichlorophenyl)-1H-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3-enamide (1445331-54-3) + SX,5-chloro-4-({2-[6-(4-chlorophenoxy)pyridin-3-yl]ethyl}amino)-6-methylpyrimidine (1605340-92-8) + SX, 4,4-dimethyl-2-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)isoxazolidin-3-one (2098918-25-1) + SX, 5,5-dimethyl-2-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)isoxazolidin-3-one (2098918-26-2) + SX, N-ethyl-2-methyl-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propanamide + SX, N,2-dimethoxy-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propanamide + SX, N-methoxy-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)cyclopropanecarboxamide + SX, N-methoxy-N'-methyl-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)urea + SX, N'-ethyl-N-methoxy-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)urea + SX, N,N'-dimethoxy-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)urea + SX,N-acetyl-2-(ethanesulfonyl)-N-[2-(methoxycarbonyl)-4-(trifluoromethoxy)phenyl]-4-(trifluoromethyl)benzamide (2043675-28-9) + SX, 3-(4-bromo-7-fluoroindol-1-yl)butan-2-yl N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate + SX, 3-(7-bromoindol-1-yl)butan-2-yl N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate + SX, 3-(7-bromo-4-fluoroindol-1-yl)butan-2-yl N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate + SX, 3-(3,5-dichloropyridin-2-yl)butan-2-yl N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate + SX, 3-(3,5-dichloropyridin-2-yl)butan-2-yl N-{[3-(acetoxymethoxy)-4-methoxypyridin-2-yl]carbonyl}-L-alaninate + SX, (1S)-1-[1-(naphthalen-1-yl)cyclopropyl]ethyl N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate + SX, (1S)-1-[1-(naphthalen-1-yl)cyclopropyl]ethyl N-[(3-acetoxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate + SX, (1S)-1-[1-(naphthalen-1-yl)cyclopropyl]ethyl N-{[3-(acetoxymethoxy)-4-methoxypyridin-2-yl]carbonyl}-L-alaninate + SX,N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)cyclopropanecarboxamide + SX, N-allyl-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)acetamide + SX, N-allyl-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propanamide + SX, N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propanamide + SX, 3,3,3-trifluoro-N-({2-fluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propanamide + SX, 3,3,3-trifluoro-N-({3-fluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propanamide + SX, 3,3,3-trifluoro-N-({2,3-difluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propanamide + SX, N-({2,3-difluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)butanamide + SX, N-methoxy-N-methyl-N'-({ 4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)urea + SX, N,N-diethyl-N'-({ 4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)urea + SX, N-methyl-N'-({ 4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)urea + SX, 1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)pyrrolidin-2-one + SX, 1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)piperidin-2-one + SX, 4-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)morpholin-3-one + SX, 2-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)isoxazolidin-3-one + SX, 3,3-dimethyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)piperidin-2-one + SX, 2-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1,2-oxazinan-3-one + SX, 1-({3-fluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)azepan-2-one + SX, 4,4-dimethyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)pyrrolidin-2-one + SX, 5-methyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)pyrrolidin-2-one + SX, ethyl 1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-pyrazole-4-carboxylate + SX, N-methyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-pyrazole-4-carboxamide + SX, N-propyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-pyrazole-4-carboxamide + SX, N-methoxy-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-pyrazole-4-carboxamide + SX, N-methoxy-N-methyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-pyrazole-4-carboxamide + SX, N,N-dimethyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-1,2,4-triazol-3-amine + SX, N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide + SX, methyl 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propanoate + SX, ethyl 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propanoate + SX, methyl 2-[2-(trifluoromethyl)-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propanoate + SX, 1-(2,3-dimethylpyridin-5-yl)-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline + SX, 1-[2-(difluoromethyl)-3-methylpyridin-5-yl]-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline + SX, 2,2-difluoro-N-[6-({[1-(1-methyl-1H-tetrazol-5-yl)benzimidazol-2-yl]oxy}methyl)pyridin-2-yl]-2-phenoxyacetamide + SX, 1-[2-(1-chlorocyclopropyl)-3-(3-chloro-2-fluorophenyl)-2-hydroxypropyl]-1H-imidazole-5-carbonitrile + SX, ethyl 1-[(4-{[2-(trifluoromethyl)-1,3-dioxolan-2-yl]methoxy}phenyl)methyl]-1H-pyrazole-4-carboxylate + SX, ethyl 1-[(4-{[(1Z)-2-ethoxy-3,3,3-trifluoro-1-propen-1-yl]oxy}phenyl)methyl]-1H-pyrazole-4-carboxylate + SX, 6-chloro-3-(3-cyclopropyl-2-fluorophenoxy)-N-[2-(2,4-dimethylphenyl)-2,2-difluoroethyl]-5-methylpyridazine-4-carboxamide + SX, 6-chloro-3-(3-cyclopropyl-2-fluorophenoxy)-N-[2-(3,4-dimethylphenyl)-2,2-difluoroethyl]-5-methylpyridazine-4-carboxamide + SX, 6-chloro-N-[2-(2-chloro-4-methylphenyl)-2,2-difluoroethyl]-3-(3-cyclopropyl-2-fluorophenoxy)-5-methylpyridazine-4-carboxamide + SX, 2-[cyano(2,6-difluoropyridin-4-yl)amino]-N-(2,2-dimethylcyclobutyl)-5-methylthiazole-4-carboxamide + SX, 2-[cyano(2,6-difluoropyridin-4-yl)amino]-N-(spiro[3.4]octan-1-yl)-5-methylthiazole-4-carboxamide + SX, 2-[cyano(2,6-difluoropyridin-4-yl)amino]-N-hexyl-5-methylthiazole-4-carboxamide + SX, 2-[acetyl(2,6-difluoropyridin-4-yl)amino]-N-(2,2-dimethylcyclobutyl)-5-methylthiazole-4-carboxamide + SX, 2-[(2-methoxyacetyl)(2,6-difluoropyridin-4-yl)amino]-N-(2,2-dimethylcyclobutyl)-5-methylthiazole-4-carboxamide + SX, 2-[(2-methylpropanoyl)(2,6-difluoropyridin-4-yl)amino]-N-(2,2-dimethylcyclobutyl)-5-methylthiazole-4-carboxamide + SX, 2-[(2,6-difluoropyridin-4-yl)amino]-N-(2,2-dimethylcyclobutyl)-5-methylthiazole-4-carboxamide + SX, 2-{[(oxetan-3-yl)carbonyl](2,6-difluoropyridin-4-yl)amino}-N-(2,2-dimethylcyclobutyl)-5-methylthiazole-4-carboxamide + SX, 2-{[(oxolan-3-yl)carbonyl](2,6-difluoropyridin-4-yl)amino}-N-(2,2-dimethylcyclobutyl)-5-methylthiazole-4-carboxamide + SX, 2-{[(oxan-4-yl)carbonyl](2,6-difluoropyridin-4-yl)amino}-N-(2,2-dimethylcyclobutyl)-5-methylthiazole-4-carboxamide + SX,5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(2-fluorophenyl)ethyl]pyrimidin-2-amine + SX, 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(2,6-difluorophenyl)ethyl]pyrimidin-2-amine + SX, 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(3,5-difluorophenyl)ethyl]pyrimidin-2-amine + SX, 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(6-chloropyridin-3-yl)ethyl]pyrimidin-2-amine + SX, 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(2-fluorophenyl)cyclopropyl]pyrimidin-2-amine + SX, 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(2,6-difluorophenyl)cyclopropyl]pyrimidin-2-amine + SX, 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(2-fluoro-3-methoxyphenyl)cyclopropyl]pyrimidin-2-amine + SX, 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-2-{[1-(2,6-difluorophenyl)cyclopropyl]oxy}pyrimidine + SX, 3-[3-(3-cyclopropyl-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-[(2,4-dimethylphenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine + SX,(5S)-3-[3-(3-cyclopropyl-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-[(2,4-dimethylphenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine + SX, 3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-[(4-bromo-2-methylphenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine + SX, 3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-[(2-chloro-4-methylphenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine + SX, (5S)-3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-[(2-chloro-4-methylphenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine + SX, (5R)-3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-[(2-chloro-4-methylphenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine + SX, N-((2S)-1-{3-[2-(5-fluoro-2-methoxyphenyl)-2-hydroxyethyl]-5-[(E)-1-(isopropoxyimino)ethyl]-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl}-3-methylbutan-2-yl)-2-methylpropanamide + SX, N-((2S)-1-{3-[2-(5-fluoro-2-methoxyphenyl)-2-hydroxyethyl]-5-[(E)-1-(isopropoxyimino)ethyl]-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl}-3-methylbutan-2-yl)-2,2-dimethylpropanamide + SX, N-((2S)-1-{3-[2-(5-fluoro-2-methoxyphenyl)-2-hydroxyethyl]-5-[(E)-1-(isopropoxyimino)ethyl]-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl}propan-2-yl)-2-methylpropanamide + SX, N-((2S)-1-{3-[2-(2-methoxyphenyl)-2-hydroxyethyl]-5-[(E)-1-(isopropoxyimino)ethyl]-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl}propan-2-yl)-2-methylpropanamide + SX, N-((2S)-1-{3-[2-(5-fluoro-2-methoxyphenyl)-2-(2-cyanoethoxy)ethyl]-5-[1-(isopropoxyimino)ethyl]-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl}propan-2-yl)-2-methylpropanamide + SX, methyl ({5-[1-(2,6-difluoro-4-isopropylphenyl)-1H-pyrazol-3-yl]-2-methylphenyl}methyl)carbamate + SX, methyl ({5-[1-(2,6-difluoro-4-cyclopropylphenyl)-1H-pyrazol-3-yl]-2-methylphenyl}methyl)carbamate + SX, methyl ({5-[1-(2,6-difluoro-4-methoxyphenyl)-1H-pyrazol-3-yl]-2-methylphenyl}methyl)carbamate + SX, 1-(4,5-dimethyl-1H-benzimidazol-1-yl)-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline + SX, 1-(4,5-dimethyl-1H-benzimidazol-1-yl)-4,4,5-trifluoro-3,3-dimethyl-3,4-dihydroisoquinoline + SX, 1-(pyrazolo[1,5-a]pyridin-3-yl)-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline + SX, 1-(6,7-dimethylpyrazolo[1,5-a]pyridin-3-yl)-6-fluoro-3,3-dimethylisoquinolin-4(3H)-one + SX, N-[2-(pyridin-2-yl)-2-(1-methylpyrazol-4-yl)propyl]-5-(2,4-difluorophenyl)isoxazole-3-carboxamide + SX, N-[2-(6-chloropyridin-2-yl)-2-(1-methylpyrazol-4-yl)propyl]-5-(2,4-difluorophenyl)isoxazole-3-carboxamide + SX, N-[2-(6-cyanopyridin-2-yl)-2-(1-methylpyrazol-4-yl)propyl]-5-(2,4-difluorophenyl)isoxazole-3-carboxamide + SX, N-[(2S)-2-(6-chloro-4-methoxypyridin-2-yl)-2-(1-methylpyrazol-4-yl)propyl]-5-(2,4-difluorophenyl)isoxazole-3-carboxamide + SX, N-[(2R)-2-(6-chloro-4-methoxypyridin-2-yl)-2-(1-methylpyrazol-4-yl)propyl]-5-(2,4-difluorophenyl)isoxazole-3-carboxamide + SX, N-(2-{6-[(1E)-(methoxyimino)ethyl]pyridin-2-yl}-2-(1-methylpyrazol-4-yl)propyl)-5-(2,4-difluorophenyl)isoxazole-3-carboxamide + SX, N-[2-(5-methylpyridin-2-yl)-2-(1-methylpyrazol-4-yl)propyl]-5-(2,4-difluorophenyl)isoxazole-3-carboxamide + SX, N-[2-(6-chloropyridin-2-yl)-2-(1-methylpyrazol-4-yl)propyl]-5-(2,4-dichlorophenyl)isoxazole-3-carboxamide + SX, methyl 6-(2-{[5-(2,4-difluorophenyl)isoxazole-3-carbonyl]amino}-1-methyl-1-(1-methylpyrazol-4-yl)ethyl)pyridine-3-carboxylate + SX, N-[2-(6-chloropyridin-2-yl)-2-(1-methylpyrazol-4-yl)propyl]-5-(3,5-difluoropyridin-2-yl)isoxazole-3-carboxamide + SX, N-[2-(6-chloropyridin-2-yl)-2-(1-methylpyrazol-4-yl)propyl]-3-(2,4-difluorophenyl)-1,2,4-oxadiazole-5-carboxamide + SX, N-[2-(6-chloropyridin-2-yl)-2-(1-methylpyrazol-4-yl)propyl]-5-(2,4-difluorophenyl)-1,3,4-thiadiazole-2-carboxamide + SX, N-[2-(5-chloropyridin-2-yl)-2-(1-methylpyrazol-4-yl)propyl]-5-(2,4-difluorophenyl)-1,3,4-thiadiazole-2-carboxamide + SX, N-[2-(6-chloropyridin-2-yl)-2-(1-methylpyrazol-4-yl)propyl]-5-(3,5-difluoropyridin-2-yl)-1,3,4-thiadiazole-2-carboxamide + SX, N-[2-(6-cyanopyridin-2-yl)-2-(1-methylpyrazol-4-yl)propyl]-5-(3,5-difluoropyridin-2-yl)-1,3,4-thiadiazole-2-carboxamide + SX, N-[2-(6-chloropyridin-2-yl)-2-(1-methylpyrazol-4-yl)propyl]-5-(2,6-difluoropyridin-3-yl)-1,3,4-thiadiazole-2-carboxamide + SX, Agrobacterium radiobactor strain K1026 + SX, Agrobacterium radiobactor strain K84 + SX, Bacillus amyloliquefaciens strain PTA-4838 (Aveo(TM) EZ Nematicide) + SX, Bacillus amyloliquefaciens strain AT332 + SX, Bacillus amyloliquefaciens strain B3 + SX, Bacillus amyloliquefaciens strain D747 + SX, Bacillus amyloliquefaciens strain DB101 + SX, Bacillus amyloliquefaciens strain DB102 + SX, Bacillus amyloliquefaciens strain GB03 + SX, Bacillus amyloliquefaciens strain FZB24 + SX, Bacillus amyloliquefaciens strain FZB42 + SX, Bacillus amyloliquefaciens strain IN937a + SX, Bacillus amyloliquefaciens strain MBI600 + SX, Bacillus amyloliquefaciens strain QST713 + SX, Bacillus amyloliquefaciens isolate strain B246 + SX, Bacillus amyloliquefaciens strain F727 + SX, Bacillus amyloliquefaciens subsp. plantarum strain D747 + SX,Bacillus licheniformis strain HB-2 + SX, Bacillus licheniformis strain SB3086 + SX, Bacillus pumilus strain AQ717 + SX, Bacillus pumilus strain BUF-33 + SX, Bacillus pumilus strain GB34 + SX, Bacillus pumilus strain QST2808 + SX, Bacillus simplex strain CGF2856 + SX, Bacillus subtilis strain AQ153 + SX, Bacillus subtilis strain AQ743 + SX, Bacillus subtilis strain BU1814 + SX, Bacillus subtilis strain D747 + SX, Bacillus subtilis strain DB101 + SX, Bacillus subtilis strain FZB24 + SX, Bacillus subtilis strain GB03 + SX, Bacillus subtilis strain HAI0404 + SX, Bacillus subtilis strain IAB / BS03 + SX, Bacillus subtilis strain MBI600 + SX, Bacillus subtilis strain QST30002 / AQ30002 + SX, Bacillus subtilis strain QST30004 / AQ30004 + SX, Bacillus subtilis strain QST713 + SX, Bacillus subtilis strain QST714 + SX, Bacillus subtilis var. Amyloliquefaciens strain FZB24 + SX, Bacillus subtilis strain Y1336 + SX, Burkholderia cepacia + SX, Burkholderia cepacia type Wisconsin strain J82 + SX,Burkholderia cepacia type Wisconsin strain M54 + SX, Candida oleophila strain O + SX, Candida saitoana + SX, Chaetomium cupreum + SX, Clonostachys rosea + SX, Coniothyrium minitans strain CGMCC8325 + SX, Coniothyrium minitans strain CON / M / 91-8 + SX, cryptococcus albidus + SX, Erwinia carotovora subsp. carotovora strain CGE234M403 + SX, Fusarium oxysporum strain Fo47 + SX, Gliocladium catenulatum strain J1446 + SX, Paenibacillus polymyxa strain AC-1 + SX, Paenibacillus polymyxa strain BS-0105 + SX, Pantoea agglomerans strain E325 + SX, Phlebiopsis gigantea strain VRA1992 + SX, Pseudomonas aureofaciens strain TX-1 + SX, Pseudomonas chlororaphis strain 63-28 + SX, Pseudomonas chlororaphis strain AFS009 + SX, Pseudomonas chlororaphis strain MA342 + SX, Pseudomonas fluorescens strain 1629RS + SX, Pseudomonas fluorescens strain A506 + SX, Pseudomonas fluorescens strain CL145A + SX, Pseudomonas fluorescens strain G7090 + SX, Pseudomonas sp. strain CAB-02 + SX,Pseudomonas syringae strain 742RS + SX, Pseudomonas syringae strain MA-4 + SX, Pseudozyma flocculosa strain PF-A22UL + SX, Pseudomonas rhodesiae strain HAI-0804 + SX, Pythium oligandrum strain DV74 + SX, Pythium oligandrum strain M1 + SX, Streptomyces griseoviridis strain K61 + SX, Streptomyces lydicus strain WYCD108US + SX, Streptomyces lydicus strain WYEC108 + SX, Talaromyces flavus strain SAY-Y-94-01 + SX, Talaromyces flavus strain V117b + SX, Trichoderma asperellum strain ICC012 + SX, Trichoderma asperellum SKT-1 + SX, Trichoderma asperellum strain T25 + SX, Trichoderma asperellum strain T34 + SX, Trichoderma asperellum strain TV1 + SX, Trichoderma atroviride strain CNCM 1-1237 + SX, Trichoderma atroviride strain LC52 + SX, Trichoderma atroviride strain IMI 206040 + SX, Trichoderma atroviride strain SC1 + SX, Trichoderma atroviride strain SKT-1 + SX, Trichoderma atroviride strain T11 + SX, Trichoderma gamsii strain ICC080 + SX, Trichoderma harzianum strain 21 + SX,Trichoderma harzianum strain DB104 + SX, Trichoderma harzianum strain DSM 14944 + SX, Trichoderma harzianum strain ESALQ-1303 + SX, Trichoderma harzianum strain ESALQ-1306 + SX, Trichoderma harzianum strain IIHR-Th-2 + SX, Trichoderma harzianum strain ITEM908 + SX, Trichoderma harzianum strain kd + SX, Trichoderma harzianum strain MO1 + SX, Trichoderma harzianum strain SF + SX, Trichoderma harzianum strain T22 + SX, Trichoderma harzianum strain T39 + SX, Trichoderma harzianum strain T78 + SX, Trichoderma harzianum strain TH35 + SX, Trichoderma polysporum strain IMI206039 + SX, trichoderma stromaticum + SX, Trichoderma virens strain G-41 + SX, Trichoderma virens strain GL-21 + SX, Trichoderma viride + SX, Variovorax paradoxus strain CGF4526 + SX, Harpin protein + SX。,

[0054] Combinations of the present ingredient in group (c) above with the compound of the present invention: 1-methylcyclopropene + SX, 1,3-diphenylurea + SX, 2,3,5-triiodobenzoic acid + SX, (1H-indol-3-yl)acetic acid (IAA) + SX, 4-(1H-indol-3-yl)butyric acid (IBA) + SX, 2-(4-chloro-2-methylphenoxy)acetic acid (MCPA) + SX, 4-(4-chloro-2-methylphenoxy)butyric acid (MCPB) + SX, 4-chlorophenoxyacetic acid (4-CPA) + SX, 5-aminolevulinic acid hydrochloride + SX, 6-benzylaminopurine + SX, abscisic acid + SX, AVG (aminoethoxyvinylglycine) + SX, anisiflupurin + SX, ancymidol + SX, butralin + SX, calcium carbonate + SX, calcium chloride + SX, calcium formate + SX, calcium peroxide + SX, calcium polysulfide + SX, calcium sulfate + SX, chlormequat chloride + SX, chlorpropham + SX, choline chloride + SX, cloprop + SX, cyanamide + SX, Cyclanilide + SX,Daminozide + SX, decan-1-ol + SX, dichlorprop + SX, dikegulac + SX, dimethipin + SX, diquat + SX, ethephon + SX, ethychlozate + SX, flumetralin + SX, flurprimidol + SX, forchlorfenuron + SX, formononetin + SX, gibberellin A + SX, gibberellin A3 + SX, inabenfide + SX, Kinetin + SX, lipochitooligosaccharide SP104 + SX, maleic hydrazide + SX, mefluidide + SX, mepiquat chloride + SX, oxidized glutathione + SX, paclobutrazol + SX, pendimethalin + SX, prohexadione calcium + SX, prohydrojasmon + SX, pyraflufen-ethyl + SX, sintophen + SX, sodium 1-naphthaleneacetate + SX, sodium cyanate + SX, Thidiazuron + SX, triapenthenol + SX, tribufos + SX, trinexapac-ethyl + SX,Uniconazole-P + SX, 2-(naphthalen-1-yl)acetamide + SX, [4-oxo-4-(2-phenylethyl)amino]butyric acid + SX, Methyl 5-(trifluoromethyl)benzo[b]thiophene-2-carboxylate + SX, 3-[(6-chloro-4-phenylquinazolin-2-yl)amino]propan-1-ol + SX, Claroideoglomus etunicatum + SX, Claroideoglomus claroideum + SX, Funneliformis mosseae + SX, Gigaspora margarita + SX, Gigaspora rosea + SX, Glomus aggregatum + SX, Glomus deserticola + SX, Glomus monosporum + SX, Paraglomus brasillianum + SX, Rhizophagus clarus + SX, Rhizophagus intraradices RTI-801 + SX, Rhizophagus irregularis DAOM 197198 + SX, Azorhizobium caulinodans + SX, Azospirillum amazonense + SX, Azospirillum brasilense XOH + SX, Azospirillum brasilense Ab-V5 + SX, Azospirillum brasilense Ab-V6 + SX, Azospirillum caulinodans + SX, Azospirillum halopraeferens + SX, Azospirillum irakense + SX, Azospirillum lipoferum + SX, Bradyrhizobium elkanii SEMIA 587 + SX, Bradyrhizobium elkanii SEMIA 5019 + SX, Bradyrhizobium japonicum TA-11 + SX,Bradyrhizobium japonicum USDA 110 + SX, Bradyrhizobium liaoningense + SX, Bradyrhizobium lupini + SX, Delftia acidovorans RAY209 + SX, Mesorhizobium ciceri + SX, Mesorhizobium huakii + SX, Mesorhizobium loti + SX, Rhizobium etli + SX, Rhizobium galegae + SX, Rhizobium leguminosarum bv. Phaseoli + SX, Rhizobium leguminosarum bv. Trifolii + SX, Rhizobium leguminosarum bv. Viciae + SX, Rhizobium trifolii + SX, Rhizobium tropici + SX, Sinorhizobium fredii + SX, Sinorhizobium meliloti + SX, Zucchini Yellow Mosaik Virus weak strain + SX。,

[0055] Combinations of the present ingredient of the above group (d) with the compound of the present invention: allidochlor + SX, benoxacor + SX, cloquintocet + SX, cloquintocet-mexyl + SX, cyometrinil + SX, cyprosulfamide + SX, dichlormid + SX, dicyclonone + SX, dimepiperate + SX, disulfoton + SX, dymron + SX, fenchlorazole + SX, fenchlorazole-ethyl + SX, fenclorim + SX, Flurazole + SX, Furilazole + SX, Fluxofenim + SX, Hexim + SX, Isoxadifen + SX, Isoxadifen-ethyl + SX, Jiecaowan + SX, Jiecaoxi + SX, Mecoprop + SX, Mefenpyr + SX, Mefenpyr-ethyl + SX, Mefenpyr-diethyl + SX, Mephenate + SX, Metocamifen + SX, Oxabetrinil + SX, 1,8-Naphthalic Anhydride + SX, octane-1,8-diamine + SX, AD-67 (4-(dichloroacetyl)-1-oxa-4-azaspiro [4.5] decane) + SX, CL-304415 (4-carboxy-3,4-dihydro-2H-1-benzopyran-4-acetic acid) + SX, CSB (1-bromo-4-[(chloromethyl)sulfonyl]benzene) + SX, DKA-24 (2,2-dichloro-N-[2-oxo-2-(2-propenylamino)ethyl]-N-(2-propenyl)acetamide) + SX, MG191 (2-(dichloromethyl)-2-methyl-1,3-dioxolane) + SX, MG-838 (2-propenyl 1-oxa-4-azaspiro[4.5]decane-4-carbodithioate) + SX, PPG-1292 (2,2-dichloro-N-(1,3-dioxan-2-ylmethyl)-N-(2-propenyl)acetamide) + SX, R-28725 (3-(dichloroacetyl)-2,2-dimethyl-1,3-oxazolidine) + SX, R-29148 (3-(dichloroacetyl)-2,2,5-trimethyl-1,3-oxazolidine) + SX, TI-35 (1-(dichloroacetyl)azepane) + SX。.

[0056] Combinations of the present component of the above group (e) with the compound of the present invention: 1-dodecyl-1H-imidazole + SX, N-(2-ethylhexyl)-8,9,10-trinorborn-5-ene-2,3-dicarboximide + SX, bucarpolate + SX, N,N-dibutyl-4-chlorobenzenesulfonamide + SX, dietholate + SX, diethylmaleate + SX, Jiajizengxiaolin + SX, octachlorodipropyl ether + SX, perbutin + SX, piperonyl butoxide + SX, piperonyl cyclonene + SX, piprotal + SX, propyl isome + SX, safroxan + SX, sesamex + SX, sesamolin + SX, sulfoxide + SX, verbutin + SX, 1,1-bis(4-chlorophenyl)ethanol (DMC) + SX, 1,1-bis(4-chlorophenyl)-2,2,2-trifluoroethanol (FDMC) + SX, 1,2-epoxy-1,2,3,4-tetrahydronaphthalene (ETN) + SX, 1,1,1-trichloro-2,3-expoxypropane (ETP) + SX, PSCP (phenylsaligenin cyclic phosphate) + SX, TBPT (S,S,S-tributyl phosphorotrithioate) + SX,TPP (triphenyl phosphate) + SX。,

[0057] Combinations of the present ingredient in group (f) above with the compound of the present invention: 2,3,6-trichlorobenzoic acid (2,3,6-TBA) + SX, 2,3,6-TBA dimethylammonium + SX, 2,3,6-TBA lithium salt + SX, 2,3,6-TBA potassium salt + SX, 2,3,6-TBA sodium salt + SX, 2,4-D + SX, 2,4-D choline salt + SX, 2,4-D biproamine + SX, 2,4-D doboxyl + SX, 2,4-D 2,4-D-2-ethylhexyl + SX, 2,4-D-3-butoxypropyl + SX, 2,4-D-ammonium + SX, 2,4-D-butotyl + SX, 2,4-D-butyl + SX, 2,4-D-diethylammonium + SX, 2,4-D-dimethylammonium + SX, 2,4-D-diolamine + SX, 2,4-D-dodecylammonium + SX, 2,4-D-ethyl + SX, 2,4-D-heptylammonium + SX, 2,4-D-isobutyl + SX, 2,4-D-isooctyl + SX, 2,4-D-isopropyl + SX, 2,4-D-isopropylammonium + SX, 2,4-D-lithium + SX, 2,4-D-meptyl + SX, 2,4-D-methyl4-D-methyl + SX, 2,4-D-octyl + SX, 2,4-D-pentyl + SX, 2,4-D-propyl + SX, 2,4-D-sodium + SX, 2,4-D-tefuryl + SX, 2,4-D-tetradecylammonium + SX, 2,4-D-triethylammonium + SX, 2,4-D-tris(2-hydroxypropyl)ammonium + SX, 2,4-D-trolamine + SX, 2,4-DB + SX, 2,4-DB choline salt + SX, 2,4-DB biproamine + SX, 2,4-DB butyl + SX, 2,4-DB dimethylammonium + SX, 2,4-DB isoctyl + SX, 2,4-DB potassium salt + SX, 2,4-DB sodium salt + SX, acetochlor + SX, acifluorfen + SX, acifluorfen sodium + SX, aclonifen + SX, 2-amino-3-chloronaphthalene-1,4-dione (ACN) + SX, alachlor + SX, allidochlor + SX, alloxydim + SX, ametryn + SX, amicarbazone + SX, amidosulfuron + SX, aminocyclopyrachlor + SX,Aminocyclopyrachlor-methyl + SX, aminocyclopyrachlor-potassium + SX, aminopyralid + SX, aminopyralid choline salt + SX, aminopyralid-potassium + SX, aminopyralid-tripromine + SX, amiprophos-methyl + SX, amitrole + SX, anilofos + SX, asulam + SX, atrazine + SX, azafenidin + SX, azimsulfuron + SX, beflubutamid + SX Benazolin-ethyl + SX, bencarbazone + SX, benfluralin + SX, benfuresate + SX, benquitrione + SX, bensulfuron + SX, bensulfuron-methyl + SX, bensulide + SX, bentazon + SX, benthiocarb + SX, benzfendizone + SX, benzobicyclon + SX, benzofenap + SX, benzthiazuron + SX, bialaphos + SX, Bicyclopyrone + SX, Bifenox + SX, Bipyrazone + SX, Bispyribac + SX, Bispyribac-sodium + SX,Bixlozone + SX, broclozone + SX, bromacil + SX, bromobutide + SX, bromofenoxim + SX, bromoxynil + SX, bromoxynil octanoate + SX, butachlor + SX, butafenacil + SX, butamifos + SX, butralin + SX, butroxydim + SX, butyrate + SX, cafenstrole + SX, carbetamide + SX, carfentrazone + SX SX, carfentrazone-ethyl + SX, chlomethoxyfen + SX, chloramben + SX, chloridazon + SX, chlorimuron + SX, chlorimuron-ethyl + SX, chlorbromuron + SX, chlorotoluron + SX, chloroxuron + SX, chlorpropham + SX, chlorsulfuron + SX, chlorthal-dimethyl + SX, chlorthiamid + SX, cinflubrolin + SX, cinidon + SX, cinidon-ethyl + SX, cinmethylin + SX, cinosulfuron + SX, clethodim + SX, clodinafop + SX,Clodinafop-propargyl + SX, clomazone + SX, clomeprop + SX, clopyralid + SX, clopyralid choline salt + SX, clopyralid-methyl + SX, clopyralid-olamine + SX, clopyralid-potassium + SX, clopyralid-tris(2-hydroxypropyl)ammonium + SX, cloransulam + SX, cloransulam-methyl + SX, cumyluron + SX, cyanazine + SX Cyclopyranil + SX, cycloate + SX, cyclopyrimorate + SX, cyclosulfamuron + SX, cycloxydim + SX, cyhalofop + SX, cyhalofop-butyl + SX, cypyrafluone + SX, daimuron + SX, dalapon + SX, dazomet + SX, desmedipham + SX, desmetryn + SX, diallate + SX, dicamba + SX, dicamba choline salt + SX Dicambabiproamine + SX, Dicambatrolamine + SX, Dicambadiglycolamine + SX,Dicamba dimethylammonium + SX, dicamba diolamine + SX, dicamba isopropylammonium + SX, dicamba methyl + SX, dicamba olamine + SX, dicamba potassium + SX, dicamba sodium + SX, dichlobenil + SX, dichlorprop + SX, dichlorprop choline + SX, dichlorprop biproamine + SX, dichlorprop etexyl + SX, dichlorprop butotyl + SX Dichlorprop-dimethylammonium + SX, dichlorprop-ethylammonium + SX, dichlorprop-isoctyl + SX, dichlorprop-methyl + SX, dichlorprop-P + SX, dichlorprop-P choline salt + SX, dichlorprop-P-biproamine + SX, dichlorprop-P-etexyl + SX, dichlorprop-P-dimethylammonium + SX, dichlorprop-potassium + SX, dichlorprop-sodium + SX Diclofop + SX,Diclofop-methyl + SX, diclosulam + SX, difenoxuron + SX, difenzoquat + SX, difenzoquat methylsulfate + SX, diflufenican + SX, diflufenzopyr + SX, diflufenzopyr sodium + SX, dimefuron + SX, dimepiperate + SX, dimepyrolimet + SX, dimesulfazet + SX, dimethachlor + SX Dimethametryn + SX, dimethenamid + SX, dimethenamid-P + SX, dimepiperate + SX, dinitramine + SX, dinoseb + SX, dinoterb + SX, dioxopyritrione + SX, diphenamid + SX, diquat + SX, diquat-dibromide + SX, disodium methylarsonate (DSMA) + SX, dithiopyr + SX, diuron + SX, 2-methyl-4,6-dinitrophenol (DNOC) + SX, esprocarb + SX, epirifenacil + SX, ethalfluralin + SX, ethametsulfuron + SX, ethametsulfuron-methyl + SX, ethidimuron + SX, ethofumesate + SX,Ethoxyfen-ethyl + SX, ethoxysulfuron + SX, etobenzanid + SX, fenoxaprop + SX, fenoxaprop-ethyl + SX, fenoxaprop-P + SX, fenoxaprop-P-ethyl + SX, fenoxasulfone + SX, fenpyrazone + SX, fenquinotrione + SX, fentrazamide + SX, fenuron + SX, feproxydim + SX, flamprop-M + SX SX, flazasulfuron + SX, florasulam + SX, florpyrauxifen + SX, florpyrauxifen-benzyl + SX, fluazifop + SX, fluazifop-butyl + SX, fluazifop-P + SX, fluazifop-P-butyl + SX, fluazolate + SX, flucarbazone + SX, flucarbazone-sodium + SX, flucetosulfuron + SX, fluchloraminopyr + SX Fluchloraminopyr-tefuryl + SX, Flufenacet + SX, Flufenauxirim + SX, Flufenauxirim-metotyl + SX, Flufenazopyr + SX,Flufenoximacil + SX, flufenpyr + SX, flufenpyr-ethyl + SX, flumetsulam + SX, flumetsulam + SX, flumiclorac + SX, flumioxazin + SX, fluometuron + SX, fluoroglycofen-ethyl + SX, flupoxam + SX, flupropanate + SX, flupyrsulfuron + SX, flupyrsulfuron-methyl-sodium + SX, Flurenol + SX, fluridone + SX, flurochloridone + SX, fluroxypyr + SX, fluroxypyr-butometyl + SX, fluroxypyr-meptyl + SX, flurtamone + SX, flusulfinam + SX, fluthiacet + SX, fluthiacet-methyl + SX, fomesafen + SX, fomesafen-sodium + SX, foramsulfuron + SX, fosamine + SX, glufosinate + SX, glufosinate-ammonium + SX, glufosinate-P + SX, glufosinate-P-ammonium + SX,Glufosinate-P-sodium + SX, glyphosate + SX, glyphosate choline + SX, glyphosate-isopropylammonium + SX, glyphosate-biproamine + SX, glyphosate-ammonium + SX, glyphosate-diammonium + SX, glyphosate-potassium + SX, glyphosate-sodium + SX, glyphosate-trimesium + SX, halauxifen + SX Halauxifen-benzyl + SX, halauxifen-methyl + SX, halosafen + SX, halosulfuron + SX, halosulfuron-methyl + SX, haloxyfop + SX, haloxyfop-ethotyl + SX, haloxyfop-methyl + SX, haloxyfop-P + SX, haloxyfop-P-ethotyl + SX, haloxyfop-P-methyl + SX, hexazinone + SX, icafolin + SX, icafolin-methyl + SX Imazamethabenz + SX, Imazamethabenz-methyl + SX, Imazamox + SX, Imazamox-ammonium + SX,Imazamox sodium + SX, imazapic + SX, imazapic ammonium + SX, imazapyr + SX, imazapyr ammonium + SX, imazapyr isopropylammonium + SX, imazaquin + SX, imazaquin ammonium + SX, imazethapyr + SX, imazethapyr ammonium + SX, imazosulfuron + SX, indanofan + SX, indaziflam + SX, indolauxipyr + SX Indolauxipyr-cyanomethyl + SX, iodosulfuron + SX, iodosulfuron-methyl-sodium + SX, iofensulfuron + SX, iofensulfuron-sodium + SX, ioxynil + SX, ioxynil-octanoate + SX, ipfencarbazone + SX, iptriazopyrid + SX, isoproturon + SX, isouron + SX, isoxaben + SX, isoxachlortole + SX Isoxafenacil + SX, Isoxaflutole + SX, Lactofen + SX, Lenacil + SX, Linuron + SX,Maleic hydrazide + SX, MCPA (2-(4-chloro-2-methylphenoxy)acetic acid) + SX, MCPA choline salt + SX, MCPA-biproamine + SX, MCPA-etexyl + SX, MCPA-butotyl + SX, MCPA-butyl + SX, MCPA-dimethylammonium + SX, MCPA-diolamine + SX, MCPA-ethyl + SX, MCPA-isobutyl + SX, MCPA-isoctyl + SX, MCPA-isopropyl + SX, MCPA-methyl + SX MCPA olamine salt (MCPA-olamine) + SX, MCPA sodium salt (MCPA-sodium) + SX, MCPA trolamine salt (MCPA-trolamine) + SX, MCPB (4-(4-chloro-2-methylphenoxy)butanoic acid) + SX, MCPB choline salt (MCPB-choline salt) + SX, MCPB-biproamine + SX, MCPB-ethyl + SX, MCPB-methyl + SX, MCPB-sodium salt (MCPB-sodium) + SX, mecoprop + SX, mecoprop choline salt (mecoprop choline salt) + SX, mecoprop-biproamine + SX, mecoprop-2-ethylhexyl + SX Mecoprop-dimethylammonium + SX, Mecoprop-diolamine + SX,Mecoprop-ethadyl + SX, mecoprop-isoctyl + SX, mecoprop-methyl + SX, mecoprop-potassium + SX, mecoprop-sodium + SX, mecoprop-trolamine + SX, mecoprop-P + SX, mecoprop-P choline + SX, mecoprop-P-2-ethylhexyl + SX, mecoprop-P-dimethylammonium + SX, mecoprop-P-isobutyl + SX Mecoprop-P-potassium + SX, mefenacet + SX, mesosulfuron + SX, mesosulfuron-methyl + SX, mesotrione + SX, metam + SX, metamifop + SX, metamitron + SX, metazachlor + SX, metazosulfuron + SX, methabenzthiazuron + SX, methiozolin + SX, methyldymron + SX, metobromuron + SX, metolachlor + SX Metosulam + SX, metoxuron + SX, metproxybicyclone + SX, metribuzin + SX, metsulfuron + SX, metsulfuron-methyl + SX,Molinate + SX, monolinuron + SX, naproanilide + SX, naproxenic acid ... Oxaziclomefone + SX, oxyfluorfen + SX, paraquat + SX, paraquat-dichloride + SX, pebulate + SX, pelargonic acid + SX, pendimethalin + SX, penoxsulam + SX, pentanochlor + SX, pentoxazone + SX, pethoxamid + SX, phenisopham + SX, phenmedipham + SX, picloram + SX, picolinafen + SX, pinoxaden + SX, piperophos + SX, pretilachlor + SX, primisulfuron + SX, primisulfuron-methyl + SX, prochlorosulfone + SX, prodiamine + SX,Profluazol + SX, Propoxydim + SX, Prometon + SX, Prometryn + SX, Propachlor + SX, Propanil + SX, Propaquizafop + SX, Propazine + SX, Propham + SX, Propisochlor + SX, Propoxycarbazone + SX, Propoxycarbazone sodium + SX, Propyrisulfuron + SX, Propyzamide + SX, Prosulfocarb + SX, Prosulfuron + SX, Pyraclonil + SX Pyraquinate + SX, pyraflufen-ethyl + SX, pyrasulfotole + SX, pyrazolinate + SX, pyrazosulfuron + SX, pyrazosulfuron-ethyl + SX, pyrazoxyfen + SX, pyribenzoxim + SX, pyributicarb + SX, pyridafol + SX, pyridate + SX, pyriflubenzoxim + SX, pyriftalid + SX, pyriminobac + SX Pyriminobac-methyl + SX, pyrimisulfan + SX, pyrithiobac + SX, pyrithiobac-sodium + SX,Pyroxasulfone + SX, pyroxsulam + SX, quinclorac + SX, quinmerac + SX, quizalofop + SX, quizalofop-ethyl + SX, quizalofop-tefuryl + SX, quizalofop-P + SX, quizalofop-P-ethyl + SX, quizalofop-P-tefuryl + SX, rimisoxafen + SX, rimsulfuron + SX, saflufenacil + SX, Sethoxydim + SX, EPTC (S-ethyl N,N-dipropylcarbamothioate) + SX, siduron + SX, simazine + SX, simetryn + SX, S-metolachlor + SX, MSMA (sodium hydrogen methylarsonate) + SX, sulcotrione + SX, sulfentrazone + SX, sulfometuron + SX, sulfometuron-methyl + SX, sulfosulfuron + SX, swep + SX, TCA (2,2,2-trichloroacetic acid) + SX, TCA-ammonium + SX TCA calcium (TCA-calcium) + SX, TCA ethadyl (TCA-ethadyl) + SX, TCA magnesium (TCA-magnesium) + SX, TCA sodium (TCA-sodium) + SX, tebutam + SX, tebuthiuron + SX, tefuryltrione + SX,Tembotrione + SX, tepraloxydim + SX, terbacil + SX, terbumeton + SX, terbuthylazine + SX, terbutryn + SX, tetflupyrolimet + SX, thaxtomin A + SX, thenylchlor + SX, thiazopyr + SX, thidiazimine + SX, thiencarbazone + SX, thiencarbazone-methyl + SX, thifensulfuron + SX, Thifensulfuron-methyl + SX, tiafenacil + SX, thiocarbazil + SX, tolpyralate + SX, topramezone + SX, tralkoxydim + SX, triafamone + SX, tri-allate + SX, triasulfuron + SX, triaziflam + SX, tribenuron + SX, tribenuron-methyl + SX, triclopyr + SX, triclopyr-butotyl + SX, triclopyr-ethyl + SX Triclopyr triethylammonium + SX, tridiphane + SX, trietazine + SX, trifloxysulfuron + SX, trifloxysulfuron sodium + SX,Trifludimoxazin + SX, trifluralin + SX, triflusulfuron + SX, triflusulfuron-methyl + SX, tripyrasulfone + SX, tritosulfuron + SX, vernolate + SX, 4-(4-fluorophenyl)-6-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-2-methyl-1,2,4-triazine-3,5(2H,4H)-dione + SX, 2-chloro-N-(1-methyl-1H-tetrazol-5-yl)-3-(methylthio)-4-(trifluoromethyl)benzamide + SX, 2-Methyl-N-(5-methyl-1,3,4-oxadiazol-2-yl)-3-(methanesulfonyl)-4-(trifluoromethyl)benzamide + SX, 1-{2-chloro-6-[(5-chloropyrimidin-2-yl)oxy]phenyl}-4,4,4-trifluorobutan-1-one.

[0058] The ratio of the compound of the present invention to the present component is not particularly limited, and examples thereof include a weight ratio (compound of the present invention:present component) of 1000:1 to 1:1000, 500:1 to 1:500, 100:1 to 1:100, 50:1, 20:1, 10:1, 9:1, 8:1, 7:1, 6:1, 5:1, 4:1, 3:1, 2:1, 1:1, 1:2, 1:3, 1:4, 1:5, 1:6, 1:7, 1:8, 1:9, 1:10, 1:20, 1:50, and the like.

[0059] Specific examples of targets to be controlled by the compound of the present invention include, but are not limited to, the following: Urticaceae weeds: Dwarf nettle (Urtica urens) Polygonaceae weeds: Bindweed (Polygonum convolvulus), Polygonum lapathifolium, Polygonum pensylvanicum, Polygonum persicaria, Polygonum longisetum, Willow (Polygonum aviculare), Willow (Polygonum arenastrum), Japanese knotweed (Polygonum cuspidatum), Rumex japonicus, Rumex crispus, Rumex obtusifolius, and Rumex acetosa. Portulacaceae weeds: Purslane (Portulaca oleracea) Caryophyllaceae weeds: Chickweed (Stellaria media), Cow chickweed (Stellaria aquatica), Earweed (Cerastium holosteoides), Dutch earweed (Cerastium glomeratum), Common clover (Spergula arvensis), Silene gallica. Molluginaceae weeds: Woodruff (Mollugo verticillata). Chenopodiaceae weeds: Chenopodium album, Common ragwort (Chenopodium ambrosioides), Kochia (Bassia scoparia), Salsola kali, Atriplex spp..

[0060] Amaranthaceae weeds: Amaranthus retroflexus, Amaranthus viridis, Amaranthus lividus, Amaranthus spinosus, Amaranthus hybridus, Amaranthus palmeri, Amaranthus patulus, Waterhemp (Amaranthus tuberculatus = Amaranthus rudis = Amaranthus tamariscinus), American blackweed (Amaranthus blitoides), Amaranthus deflexus, Amaranthus quitensis, Alternant weed (Alternanthera philoxeroides), Alternanthus sessilis, Sanguinaria (Alternanthera tenella) Papaveraceae: Corn poppy (Papaver rhoeas), Long-legged poppy (Papaver dubium), Thistle poppy (Argemone mexicana) Brassicaceae: Wild radish (Raphanus raphanistrum), Radish (Raphanus sativus), Field mustard (Sinapis arvensis), Shepherd's purse (Capsella bursa-pastoris), Common mustard (Brassica juncea), Common oilseed rape (Brassica napus), Descurainia pinnata, Burdock root (Rorippa islandica), Yellow mustard (Rorippa sylvestris), Shepherd's purse (Thlaspi arvense), Mountain mustard (Myagrum rugosum), Lepidium virginicum, Coronopus didymusCapparaceae weed: Cleome affinis

[0061] Legume weeds (Fabaceae): Water hyacinth (Aeschynomene indica), zigzag-jointed vetch (Aeschynomene rudis), American hornbeam (Sesbania exaltata), Slipper grass (Cassia obtusifolia), Boxweed (Cassia occidentalis), Day bush clover (Desmodium tortuosum), Field bush clover (Desmodium adscendens), Illinois bush clover (Desmodium illinoense), White clover (Trifolium repens), Kudzu (Pueraria lobata), Vetch (Vicia angustifolia), Japanese ragwort (Indigofera hirsuta), Indigofera truxillensis, Wild cowpea (Vigna sinensis). Oxalidaceae: Wood sorrel (Oxalis corniculata), Oxalis stricta, Oxalis oxyptera Geraniaceae: American buttercup (Geranium carolinense), Dutch buttercup (Erodium cicutarium) Euphorbiaceae: Spurge (Euphorbia helioscopia), Western jasmine (Euphorbia maculata), Cornus humistrata, Euphorbia esula, Cardamom (Euphorbia heterophylla), Hyssop-leaf sand mat (Euphorbia brasiliensis), Chinese hackberry (Acalypha australis), Tropic croton (Croton glandulosus), Lobed croton (Croton lobatus), Brazilian phyllanthus (Phyllanthus corcovadensis), castor bean (Ricinus communis)

[0062] Malvaceae: Abutilon theophrasti, Sida rhombifolia, Sida cordifolia, Sida spinosa, Sida glaziovii, Sida santaremnensis, Hibiscus trionum, Caladium laurel, Malvastrum coromandelianum. Onagraceae: Ludwigia epilobioides, Ludwigia octovalvis, Ludwigia decurrens, Oenothera biennis, Oenothera laciniata. Sterculiaceae (Sterculiaceae): Waltheria indica (Waltheria indica) Violaceae (Violaceae): Viola arvensis, Viola tricolor (Wild pansy) Cucurbitaceae (Cucurbitaceae): Sicyos angulatus, Echinocystis lobata, Momordica charantia (Wild bitter gourd) Lythraceae (Lythraceae): Ammannia multiflora, Ammannia auriculata, Ammannia coccinea, Lythrum salicaria, Rotala indica (Lythrum weed) Elatinaceae (Elatinaceae): Elatine triandra), California waterwort (Elatine californica)

[0063] Umbelliferae weeds (Apiaceae): Japanese parsley (Oenanthe javanica), wild carrot (Daucus carota), hemlock (Conium maculatum) Araliaceae weeds: Hydrocotyle sibthorpioides, Brazilian hydrocotyle (Hydrocotyle ranunculoides) Ceratophyllaceae weeds: Ceratophyllum demersum Cabombaceae weeds: Cabomba caroliniana Haloragaceae weeds: Water milfoil (Myriophyllum aquaticum), water milfoil (Myriophyllum verticillatum), water milfoil (Myriophyllum spicatum, Myriophyllum heterophyllum, etc.) Sapindaceae (Sapindaceae): Balloon vine (Cardiospermum halicacabum) Primulaceae (Primulaceae): Red-leaf chickweed (Anagallis arvensis) Asclepiadaceae (Asclepiadaceae): Giant milkweed (Asclepias syriaca), honeyvine milkweed (Ampelamus albidus) Rubiaceae (Rubiaceae): Catchweed bedstraw (Galium aparine), cleaver (Galium spurium var. echinospermon), broadleaf weed (Spermacoce latifolia), Brazilian false hawkweed (Richardia brasiliensis), winged phallus buttonweed (Borreria alata)

[0064] Convolvulaceae weeds: Morning glory (Ipomoea nil), American morning glory (Ipomoea hederacea), round morning glory (Ipomoea purpurea), round morning glory (Ipomoea hederacea var. integriuscula), common morning glory (Ipomoea lacunosa), starry morning glory (Ipomoea triloba), common morning glory (Ipomoea acuminata), ivy morning glory (Ipomoea hederifolia), common morning glory (Ipomoea coccinea), morning glory (Ipomoea quamoclit), Ipomoea grandifolia, Ipomoea aristolochiaefolia, sweet bindweed (Ipomoea cairica), and European bindweed (Convolvulus arvensis), Calystegia hederacea, Calystegia japonica, Merremia hederacea, Hairy woodrose (Merremia aegyptia), Roadside woodrose (Merremia cissoides), Morning glory (Jacquemontia tamnifolia) Boraginaceae: Forget-me-not (Myosotis arvensis) Lamiaceae: Lamium purpureum, Lamium amplexicaule, Leonotis nepetaefolia, Hyptis suaveolens, Hyptis lophanta, Leonurus sibiricus), Arvensis arvensis

[0065] Solanaceae weeds: Datura stramonium, Solanum nigrum, Solanum americanum, Solanum ptycanthum, Solanum sarrachoides, Solanum rostratum, Solanum aculeatissimum, Solanum sisymbriifolium, Solanum carolinense, Solanum angulata, Solanum subglabrata, Solanum persica (Nicandra physalodes). Scrophulariaceae weeds: Veronica hederaefolia, Solanum persica (Veronica persica), Veronica arvensis, Lindernia procumbens, Lindernia dubia, Lindernia angustifolia, Bacopa rotundifolia, Dopatrium junceum, Gratiola japonica. Plantaginaceae: Plantain (Plantago asiatica), Plantain lanceolata, Common plantain (Plantago major), Water chickweed (Callitriche palustris).

[0066] Asteraceae weeds: Cocklebur (Xanthium pensylvanicum), Giant cocklebur (Xanthium occidentale), Brimbur (Xanthium italicum), Wild sunflower (Helianthus annuus), Chamomile (Matricaria chamomilla), Chamomile (Matricaria perforata), Corn marigold (Chrysanthemum segetum), Oriental daisy (Matricaria matricarioides), Wormwood (Artemisia princeps), Artemisia vulgaris, Chinese mugwort (Artemisia verlotorum), Goldenrod (Solidago altissima), Dandelion (Taraxacum officinale), Dead daisy (Galinsoga ciliata), Japanese cornflower (Galinsoga parviflora), Groundsweet (Senecio vulgaris, Senecio brasiliensis, Senecio grisebachii, Ragweed (Conyza bonariensis), Ragweed (Conyza smatrensis), Artemisia canadensis, Ragweed (Ambrosia artemisiifolia), Mulberry (Ambrosia trifida), Bidens tripartita, Bidens pilosa, Bidens frondosa, Bidens subalternans, Thorn thistle (Cirsium arvense), American thistle (Cirsium vulgare), Milk thistle (Silybum marianum), Musk thistle (Carduus nutans), Lettuce (Lactuca serriola), common sowweed (Sonchus oleraceus), common sowweed (Sonchus asper), beach creeping oxeye (Wedeliaglauca), Perfoliate Blackfoot (Melampodium perfoliatum), Pale Bitter Gum (Emilia sonchifolia), Chiaroscuro (Tagetes minuta), Paracles (Blainvillea latifolia), Little Daisy (Tridax procumbens), Yerba Polosa (Porophyllum ruderale), Paraguay Starburst (Acanthospermum australe), Bristle Starburst (Acanthospermum hispidum), Balloon Vine (Cardiospermum halicacabum), Ageratum (Ageratum conyzoides), Common Boneset (Eupatorium perfoliatum), Dandlouze (Erechtites hieracifolia), American Everlasting (Gamochaeta spicata), White-legged Weevil (Gnaphalium spicatum), Jaegeria hiera (Jaegeria hirta), Cornflower (Parthenium hysterophorus), Oriental fir (Siegesbeckia orientalis), American snowdrop (Soliva sessilis), Eclipta prostrata, American snowdrop (Eclipta alba), Snowdrop (Centipeda minima)

[0067] Alismataceae: Sagittaria pygmaea, Sagittaria trifolia, Sagittaria sagittifolia, Sagittaria montevidensis, Sagittaria aginashi, Alisma canaliculatum, Alisma plantago-aquatica Limnocharitaceae: Limnocharis flava Hydrocharitaceae: Frogbit (Limnobium spongia), Hydrilla verticillata, Common water nymph (Najas guadalupensis) Araceae: Water duckweed (Pistia stratiotes) Duckweeds (Lemnaceae): Duckweed (Lemna aoukikusa, Lemna paucicostata, Lemna aequinoctialis), duckweed (Spirodela polyrhiza), water flea (Wolffia spp.)) Potamogetonaceae: Potamogeton distinctus, pondweeds (Potamogeton crispus, Potamogeton illinoensis, Stuckenia pectinata, etc.) Liliaceae: Wild onion (Allium canadense), wild garlic (Allium vineale), wild oak (Allium macrostemon) Pontederiaceae: Water hyacinth (Eichhornia crassipes), American boxwood (Heteranthera limosa), Japanese black laurel (Monochoria korsakowii), Japanese boxwood (Monochoria vaginalis) Commelinaceae: Dayflower (Commelina communis), common dayflower (Commelina benghalensis), erect dayflower (Commelina erecta), boxwood (Murdannia keisak).

[0068] Grass weeds (Poaceae): Barnyard grass (Echinochloa crus-galli), Oriental watergrass (Echinochloa oryzicola), Lesser Oriental watergrass (Echinochloa crus-galli var. formosensis), Latewatergrass (Echinochloa oryzoides), Lesser barnyard grass (Echinochloa colona), Gulf cockspur (Echinochloa crus-pavonis), Green foxtail (Setaria viridis), Setaria faberi, Golden foxtail (Setaria glauca), American green foxtail (Setaria geniculata), Large crabgrass (Digitaria ciliaris), Large crabgrass (Digitaria sanguinalis), Jamaican crabgrass (Digitaria horizontalis), Large crabgrass (Digitaria insularis), Common goosegrass (Eleusine indica), Annual bluegrass (Poa annua), Poa trivialis, Poa pratensis, Alopecurus aequalis, Blackgrass (Alopecurus myosuroides), Oat (Avena fatua), Sorghum halepense, Shattercane (Sorghum vulgare), Quackgrass (Agropyron repens), Lolium multiflorum, Lolium perenne, Lolium rigidum, Bromegrass (Bromus catharticus), Bromegrass (Bromus sterilis), Bromegrass (Bromus japonicus), Bromegrass (Bromus secalinus), Bromegrass (Bromus tectorum), Bromegrass (Hordeum jubatum), Goatgrass (Aegilops cylindrica), Reed canary grass (Phalaris arundinacea), Small canary grass (Phalarisminor), Silky bentgrass (Apera spica-venti), Common bentgrass (Panicum dichotomiflorum), Texas panicum (Panicum texanum), Guinea millet (Panicum maximum), American millet (Brachiaria platyphylla), Ruzigrass (Brachiaria ruziziensis), Alexandergrass (Brachiaria plantaginea), Surinamegrass (Brachiaria decumbens), Palisade grass (Brachiaria brizantha), Columbiagrass (Brachiaria humidicola), Sinqueweed moth (Cenchrus echinatus), Small chestnut moth (Cenchrus pauciflorus), Narco barnyard grass (Eriochloa villosa), Pennisetum (Pennisetum setosum), African brown grass (Chloris gayana), African brown grass (Chloris virgata), Eragrostis pilosa), Ruby grass (Rhynchelytrum repens), Seagrass (Dactyloctenium aegyptium), Taiwan grass (Ischaemum rugosum), Japanese bamboo grass (Isachne globosa), Wild rice (Oryza sativa), American paspalum (Paspalum notatum), Coastal sand paspalum (Paspalum maritimum), Knotgrass (Paspalum distichum), Kikuyu grass (Pennisetum clandestinum), Narrow-beaded grass (Pennisetum setosum), Horngrass (Rottboellia cochinchinensis), Japanese maple grass (Leptochloa chinensis), Japanese maple grass (Leptochloa fascicularis), Japanese threadgrass (Leptochloa filiformis), Amazon spangletop (Leptochloa panicoides), Leersia japonica, Leersiasayanuka), Siberian bog grass (Leersia oryzoides), Duckgrass (Glyceria leptorrhiza), Mutsuoregusa (Glyceria acutiflora), Loach grass (Glyceria maxima), Duckgrass (Agrostis gigantea), Siberian bog grass (Agrostis stolonifera), Corngrass (Cynodon dactylon), Orchard grass (Dactylis glomerata), Centipede grass (Eremochloa ophiuroides), Tall fescue (Festuca arundinacea), Big fescue (Festuca rubra), Imperata cylindrica, Japanese silvergrass (Miscanthus sinensis), Switchgrass (Panicum virgatum), Zoysia japonica

[0069] Cyperaceae weeds: Cyperus microiria, Cyperus iria, Cyperus compressus, Cyperus difformis, Cyperus flaccidus, Cyperus globosus, Cyperus nipponicus, Cyperus odoratus, Cyperus serotinus, Cyperus rotundus, Cyperus esculentus, Kylerius gracillima, Kylerius brevifolia, Fimbristylis miliacea, Fimbristylis japonica dichotoma), Eleocharis acicularis, Eleocharis kuroguwai, Schoenoplectiella hotarui, Schoenoplectiella juncoides, Schoenoplectiella wallichii, Schoenoplectiella mucronatus, Schoenoplectiella triangulatus, Schoenoplectiella nipponicus, Schoenoplectiella triqueter, Bolboschoenus koshevnikovii, Bolboschoenus fluviatilis. Equisetaceae weeds: Horsetail (Equisetum arvense), Horsetail (Equisetum palustre). Salviniaceae weeds: Salvinia natans Azollaceae weeds: Azolla japonica, Azolla pinnataMarsileaceae weeds: Marsilea quadrifolia Others: Filamentous algae (Pithophora, Cladophora), mosses, liverworts, hornworts, cyanobacteria, ferns, suckers of perennial crops (pome fruits, stone fruits, berries, nuts, citrus fruits, hops, grapes, etc.).

[0070] The intraspecific mutations of the above-mentioned weeds are not particularly limited. They also include those with reduced susceptibility (also known as resistance) to certain herbicides. The reduced susceptibility may be due to a mutation at the target site (site mutation) or a factor other than site mutation (non-site mutation). Site mutations include those in the open reading frame (OPF) of a nucleic acid sequence corresponding to the amino acid sequence of a protein, resulting in an amino acid substitution in the target protein, and those resulting in overexpression of the target protein due to mutations such as deletion of a suppressor sequence in the promoter region, amplification of an enhancer sequence, or increased gene copy number. Factors that can cause reduced susceptibility due to non-site mutations include enhanced metabolism, inadequate absorption, inadequate translocation, and excretion from the system. Examples of factors that can cause enhanced metabolism include increased activity of metabolic enzymes such as cytochrome P450 monooxygenase (CYP), aryl acylamidase (AAA), esterase, glutathione S-transferase (GST), and cyanoalanine nitrilase. Examples of excretion include transport to vacuoles by ABC transporters. Examples of herbicide-resistant weeds include: Glyphosate resistance: Examples of reduced susceptibility due to site-of-action mutations include weeds with one or more of the following amino acid substitutions in the EPSPS gene: Thr102Ile, Pro106Ser, Pro106Ala, Pro106Leu, and Pro106Thr. In particular, weeds with both Thr102Ile and Pro106Ser, and those with both Thr102Ile and Pro106Thr, are particularly susceptible. These site-of-action mutations effectively control glyphosate-resistant species such as goosegrass, Lolium multiflorum, Celastrus oryzae, Ryegrass, and Bidens subalternans. A similar example of glyphosate resistance involving the site of action is increased copy number of the EPSPS gene (PNAS, 2018 115 (13) 3332-3337). According to the present invention, glyphosate-resistant plants such as amaryllis, water hemp, and kochia with an increased copy number of the EPSPS gene can be effectively controlled.Examples of weeds with reduced susceptibility due to non-active point mutations include weeds with glyphosate resistance due to ABC transporters, such as Artemisia gracilis, Rattus nigra, and Rattus gracilis, which can be effectively controlled by the present invention. Another non-active point mutation is barnyardgrass, which has reduced susceptibility to glyphosate due to increased expression of aldo-keto reductase (Plant Physiology 181, 1519-1534), and this can be effectively controlled by the present invention. Resistance to ALS-inhibiting herbicides: Examples of weeds with reduced susceptibility due to active point mutations include weeds with mutations in the ALS gene that cause one or more of the following amino acid substitutions: Ala122Thr, Ala122Val, Ala122Tyr, Pro197Ser, Pro197His, Pro197Thr, Pro197Arg, Pro197Leu, Pro197Gln, Pro197Ala, Pro197Ile, Ala205Val, Ala205Phe, Asp376Glu, Asp376Gln, Asp376Asn, Arg377His, Trp574Leu, Trp574Gly, Trp574Met, Ser653Thr, Ser653Asn, Ser635Ile, Gly654Glu, Gly645Asp. The present invention effectively controls ALS inhibitor-resistant plants such as Amaranthus retroflexus, Amaranthus retroflexus, Amaranthus retroflexus, waterhemp, and Kochia japonica, which have these site-of-action mutations. Examples of weeds with reduced susceptibility due to non-active site mutations include weeds that have become resistant to ALS inhibitors due to the involvement of CYP or GST, and these can be effectively controlled by the present invention. Examples include Bomugi (grass) overexpressing CYP81A10 or CYP81A1v1, Echinochloa oryzicola overexpressing CYP81A12 or CYP81A21, and Black-legged foxtail (grass) overexpressing GSTF1 or GSTU2. ACCase inhibitor resistance: Examples of weeds with reduced susceptibility due to active site mutations include weeds with mutations in the ACCase gene that result in one or more of the following amino acid substitutions:Ile1781Ala, Ile1781Leu, Ile1781Val, Ile1781Thr, Leu1818Phe, Trp1999Cys, Trp1999Leu, Trp1999Ser, Ala2004Val, Trp2027Cys, Trp2027Leu, Ile2041Asn, Ile2041Asp, Ile2041Val, Ile2041Thr, Asp2078Gly, Asp2078Glu, Cys2088Arg, Cys2088Phe, Gly2096Ala, Gly2096Ser.According to the present invention, ACCase-resistant weeds having these site-of-action mutations can be effectively controlled. Similarly, an example of ACCase inhibitor resistance involving the site of action is increased expression of the ACCase gene (Pest Manag. Sci. 2017 Nov;73(11):2227-2235). Examples of reduced susceptibility of weeds due to non-site mutations include weeds that have become resistant to ACCase inhibitors due to CYP or GST, and these can be effectively controlled by the present invention. Examples include Bomugi (grass) overexpressing CYP81A10 or CYP81A1v1, barnyardgrass overexpressing CYP81A12, CYP81A21, or CYP709C69, and Black-legged foxtail (Japanese ragweed) overexpressing GSTF1 or GSTU2. PPO inhibitor resistance: Examples of reduced susceptibility of weeds due to site-of-action mutations include weeds with mutations in the PPO gene that result in one or more of the following amino acid substitutions. These mutations are known to confer resistance to carfentrazone-ethyl, fomesafen, or lactofen, or are predicted to confer resistance.Arg128Leu, Arg128Met, Arg128Gly, Arg128His, Arg128Ala, Arg128Cys, Arg128Glu, Arg128Ile, Arg128Lys, Arg128Asn, Arg128Gln, Arg128Ser, Arg128Thr, Arg128Val, Arg128Tyr, Gly210 deletion, Ala210 deletion, Gly210Thr, Ala210Thr, Gly211 deletion, Gly114Glu, Ser149Ile, Val361Ala, Gly399Ala (all amino acid numbers are standardized to the sequence of PPO2 from Amaranthus palmeri). Typically, weeds have two PPO genes: the PPO1 gene and the PPO2 gene. The mutation may be present in either the PPO1 gene, the PPO2 gene, or both. The mutation is preferably present in the PPO2 gene. For example, Arg128Met means that there is a mutation at the 128th amino acid. In the ragweed PPO2 gene, this mutation corresponds to the 98th amino acid (Weed Science 60, 335-344), and is known as Arg98Leu. This Arg98 is synonymous with Arg128 in this specification.In the PPO genes of weeds targeted for control by the present invention, Arg128Met and Arg128Gly are known in Amaranthus retroflexus (Pest Management Science 73, 1559-1563), Arg128Gly is known in the PPO2 of waterhemp (Pest Management Science, 2019; 75: 3235-3244), Arg128Ile and Arg128Lys are known in the PPO2 of waterhemp (Pest Management Science, 2019; 75: 3235-3244), Arg128His is known as Arg132His in the PPO2 of Bouquet (WSSA annual meeting, 2018), and Gly114Glu, Ser149Ile, Val361Ala, and Gly399Ala are known in the PPO2 of Amaranthus retroflexus (Frontiers in Plant Science 10, Article 568 and Plants 2023, 12(9), 1886), and Ala210Thr is known as Ala212Thr in PPO1 of goosegrass (Pest Management Science, doi: 10.1002 / ps.5703). According to the present invention, PPO inhibitor-resistant weeds having these site-of-action mutations can be effectively controlled, but the PPO inhibitor-resistant weeds to be controlled are not limited to these. That is, not only amaryllis plants having the Arg128Leu, Arg128Met, Arg128Gly, Arg128His, Arg128Ala, Arg128Cys, Arg128Glu, Arg128Ile, Arg128Lys, Arg128Asn, Arg128Gln, Arg128Ser, Arg128Thr, Arg128Val, Arg128Tyr, Gly210 deficiency, Ala210 deficiency, Gly210Thr, Ala210Thr, Gly211 deficiency, Gly114Glu, Ser149Ile, or Gly399Ala mutation in PPO1 or PPO2, but also, for example, waterhemp, ragweed, and dayflower having the same mutations can be effectively controlled.Examples of reduced susceptibility of weeds due to non-acting point mutations include waterhemp and amaryllis retroflexus that have become resistant to PPO inhibitors due to CYP or GST, as well as waterhemp that has become resistant to carfentrazone ethyl (PLOS ONE, doi: 10.1371 / journal.pone.0215431). These can be effectively controlled by the present invention. Resistance to auxin-based herbicides: An example of a non-acting point mutation is a mutation that causes Gly-Asn in the degron region of the AUX / IAA gene. This invention effectively controls Kochia, amaryllis retroflexus, and waterhemp that possess this mutation. Examples of non-acting point mutations include dicamba-resistant amaryllis retroflexus and 2,4-D-resistant waterhemp, which are suggested to be CYP-mediated. These can be effectively controlled by the present invention. The same applies to non-acting point mutations involving GST. HPPD inhibitor resistance: An example of HPPD inhibitor resistance involving the site of action is increased expression of the HPPD gene (Frontiers in Plant Science, 2017, 8: 555). Examples of weeds with reduced susceptibility due to non-site mutations include waterhemp and amaryllis, which have become resistant to HPPD inhibitors due to CYP or GST, and these can be effectively controlled by the present invention. Known examples include amaryllis, which overexpresses CYP72A219, CYP81B, and CYP81E8. Photosystem II inhibitor resistance: An example of weeds with reduced susceptibility due to site mutations is weeds with one or more of the following amino acid substitutions in the psbA gene: Val219Ile, Ser264Gly, Ser264Ala, and Phe274Val. The present invention effectively controls Amaranthus retroflexus and waterhemp that have these site-of-action mutations and are resistant to photosystem II inhibitors.Examples of weeds with reduced susceptibility due to non-site-of-action mutations include Amaranthus retroflexus and waterhemp that are resistant to photosystem II inhibitors due to the involvement of CYP, GST, or AAA, and these can be effectively controlled by the present invention.One example of this is known to be boumugi (a kind of weed) with overexpression of CYP71R4. Glutamate synthase inhibitor resistance: An example of reduced susceptibility in weeds due to site-of-action mutations is a weed with a mutation in the glutamine synthase gene that causes an amino acid substitution of Asp171Asn. The present invention effectively controls glutamine synthase inhibitor-resistant weeds such as ambrosia and waterhemp that have this mutation. An example of glutamate synthase inhibitor resistance involving the site of action is an increase in the copy number of the glutamate synthase gene (Weed Science, 2022, 70.4: 370-379). An example of reduced susceptibility in weeds due to non-site-of-action mutations is ambrosia and waterhemp that have become glufosinate-resistant due to CYP or GST, and these weeds are effectively controlled by the present invention. An example of such a resistant weed is ambrosia retroflexus, which overexpresses CYP72A219, CYP81B, or CYP81E8. Even resistant weeds that are "stacked" (combined) with resistance to two or more of the above groups (randomly selected group 2, randomly selected group 3, randomly selected group 4, randomly selected group 5, randomly selected group 6, group 7, or group 8) are effectively controlled. An example of a stacked resistant weed is waterhemp, which is resistant to photosystem II inhibitors, HPPD inhibitors, 2,4-D, PPO inhibitors, ALS inhibitors, and glyphosate, and is also effectively controlled. The stacked weeds may be a combination of active point mutations, a combination of non-active point mutations, or a combination of active and non-active point mutations.

[0071] The compound of the present invention or Composition A is typically formulated into aqueous suspensions, oil suspensions, oil solutions, emulsifiable concentrates, emulsions, microemulsions, microcapsule formulations, wettable powders, water dispersible granules, dusts, granules, tablets, aerosols, resin formulations, etc. by mixing an inert carrier such as a solid carrier, liquid carrier, or gaseous carrier with a surfactant, and optionally adding formulation adjuvants such as binders, dispersants, and stabilizers. In addition to these formulations, the compound of the present invention or Composition A can also be formulated into dosage forms described in the Manual on development and use of FAO and WHO Specifications for pesticides, FAO Plant Production and Protection Papers-271 to 276, prepared by the FAO / WHO Joint Meeting on Pesticide Specifications, 2016, ISSN:0259-2517. These formulations typically contain 0.0001 to 99% by weight of the compound of the present invention or Composition A.

[0072] Examples of solid carriers include clay (pyrophyllite clay, kaolin clay, etc.), talc, calcium carbonate, diatomaceous earth, zeolite, bentonite, acid clay, attapulgite, white carbon, ammonium sulfate, vermiculite, perlite, pumice, silica sand, fine powder and granular chemical fertilizers (ammonium sulfate, ammonium phosphate, ammonium nitrate, urea, ammonium chloride, etc.), and resins (polyethylene, polypropylene, polyester, polyurethane, polyamide, polyvinyl chloride, etc.).

[0073] Examples of liquid carriers include water, alcohols (ethanol, cyclohexanol, benzyl alcohol, propylene glycol, polyethylene glycol, etc.), ketones (acetone, cyclohexanone, etc.), aromatic hydrocarbons (xylene, phenylxylylethane, methylnaphthalene, etc.), aliphatic hydrocarbons (hexane, cyclohexane, etc.), esters (ethyl acetate, methyl oleate, propylene carbonate, etc.), nitriles (acetonitrile, etc.), ethers (ethylene glycol dimethyl ether, etc.), amides (N,N-dimethylformamide, N,N-dimethyloctanamide, etc.), sulfoxides (dimethyl sulfoxide, etc.), lactams (N-methylpyrrolidone, N-octylpyrrolidone, etc.), fatty acids (oleic acid, etc.), and vegetable oils (soybean oil, etc.).

[0074] Examples of gaseous carriers include fluorocarbons, butane gas, LPG (liquefied petroleum gas), dimethyl ether, nitrogen, and carbon dioxide gas.

[0075] Examples of surfactants include nonionic surfactants (polyoxyethylene alkyl ethers, polyoxyethylene alkylaryl ethers, polyethylene glycol fatty acid esters, etc.) and anionic surfactants (alkyl sulfonates, alkylaryl sulfonates, alkyl sulfates, etc.).

[0076] Other formulation adjuvants include binders, dispersants, colorants, stabilizers, etc., and specific examples include polysaccharides (starch, gum arabic, cellulose derivatives, alginic acid, etc.), lignin derivatives, synthetic water-soluble polymers (polyvinyl alcohol, polyvinylpyrrolidone, polyacrylic acids, etc.), acid isopropyl phosphate, and dibutylhydroxytoluene.

[0077] In addition, adjuvants can be used as components that enhance or support the efficacy of the compound of the present invention. Specific examples include Nimbus (registered trademark), Assist (registered trademark), Aureo (registered trademark), Iharol (registered trademark), Silwet L-77 (registered trademark), BreakThru (registered trademark), Sundance II (registered trademark), Induce (registered trademark), Penetrator (registered trademark), AgriDex (registered trademark), Lutensol A8 (registered trademark), NP-7 (registered trademark), Triton (registered trademark), Nufilm (registered trademark), Emulgator NP7 (registered trademark), Emulad (registered trademark), TRITON X 45 (registered trademark), AGRAL 90 (registered trademark), AGROTIN (registered trademark), ARPON (registered trademark), EnSpray N (registered trademark), and BANOLE (registered trademark).

[0078] The compound of the present invention can be used in agricultural land where useful plants are cultivated to control weeds in the agricultural land. Examples of the useful plants include the following.

[0079] Corn (horse-tooth, hard grain, soft grain, explosive, glutinous, sweet, field corn), rice (long grain, short grain, medium grain, japonica, tropical japonica, indica, javanica, paddy rice, upland rice, floating rice, direct-seeded rice, transplanted rice, glutinous rice), wheat (bread wheat (hard, soft, medium, red wheat, white wheat), durum wheat, spelt wheat, club wheat, each winter wheat type, spring wheat type), barley (two-row barley (= beer barley), six-row barley, naked barley, waxy barley, each winter barley type, spring barley type), rye (winter rye type, spring rye type), triticale (winter triticale type, spring triticale type), oats (winter oat type, spring oat type), sorghum, cotton (upland type, pima type), soybean (fully harvested seed varieties, edamame varieties, green-harvested varieties, indeterminate, determinate, semi-determinate types), peanuts, buckwheat, sugar beet (sugar production, animal feed, root vegetable, leafy vegetable, fuel), rapeseed (winter rapeseed type, spring rapeseed type), canola (winter canola type, spring canola type), sunflower (oil production, food, ornamental), sugarcane, tobacco, tea plant, mulberry, solanaceous vegetables (eggplant, tomato, bell pepper, chili pepper) , potatoes, etc.), Cucurbitaceae vegetables (cucumber, pumpkin, zucchini, watermelon, melon, etc.), Cruciferous vegetables (radish, turnip, horseradish, kohlrabi, Chinese cabbage, cabbage, mustard greens, broccoli, cauliflower, etc.), Asteraceae vegetables (burdock, garland chrysanthemum, artichoke, lettuce, etc.), Liliaceae vegetables (leeks, onions, garlic, asparagus, etc.), Umbelliferae vegetables (carrots, parsley, celery, parsley, etc.), Chenopodiaceae vegetables (spinach, Swiss chard, etc.), Lamiaceae vegetables (perilla, mint, basil, etc.), strawberries, sweet potatoes, yams, scallions, Sweet potatoes, pome fruits (apples, European pears, Japanese pears, Chinese pears, quince, quince, etc.), stone fruits (peaches, plums, nectarines, plums, cherries, apricots, prunes, etc.), citrus fruits (Satsuma mandarins, oranges, lemons, limes, grapefruits, etc.), nuts (chestnuts, walnuts, hazelnuts, almonds, pistachios, cashew nuts, macadamia nuts, etc.), berries (blueberries, cranberries, blackberries, raspberries, etc.), grapes, persimmons, figs, olives, loquats, bananas, coffee, dates, coconuts, ornamental plants, forest plants,Turfgrass, pasture grass,

[0080] The useful plants are not particularly limited as long as they are varieties that are commonly cultivated, and include plants that can be produced by natural crossbreeding, plants that can be generated by mutation, F1 hybrid plants, and genetically modified crops. Examples of genetically modified crops include plants that have been conferred resistance to herbicides such as HPPD (4-hydroxyphenylpyruvate dioxygenase enzyme) inhibitors such as isoxaflutole, ALS (acetolactate synthase) inhibitors such as imazethapyr and thifensulfuron methyl, EPSP (5-enolpyruvylshikimate-3-phosphate synthase) inhibitors, glutamine synthetase inhibitors, PPO (protoporphyrinogen oxidase) inhibitors, bromoxynil, or dicamba; plants that are capable of synthesizing selective toxins known to be found in the genus Bacillus, such as Bacillus thuringiensis; and plants that can be conferred specific insecticidal activity by synthesizing gene fragments that partially match endogenous genes derived from harmful insects and inducing gene silencing (RNAi; RNA interference) in the target harmful insect.

[0081] The weed control method of the present invention comprises the step of applying an effective amount of the compound of the present invention to weeds or to a place where weeds grow or will grow. 2 The compound of the present invention is usually used in an amount of 5 to 5,000 g, preferably 10 to 1,000 g, per acre. When applying the compound of the present invention or Composition A, a spraying device can be used. Examples of devices used for application include a hand-cranked sprayer, a power sprayer, a pancrusher sprayer, a manned aircraft (such as a manned helicopter), an unmanned aircraft (such as a radio-controlled helicopter or drone), a tractor, a planter, and the like. Alternatively, the compound may be applied by hand without using a spraying device.

[0082] In the weed control method of the present invention, the compound of the present invention is usually used in the form of the herbicidal composition of the present invention. Examples of the weed control method of the present invention include a method of foliar application of the herbicidal composition of the present invention to weeds, a method of applying the herbicidal composition of the present invention to the soil surface where weeds grow or are likely to grow, a method of incorporation of the herbicidal composition of the present invention into soil where weeds grow, and a method of applying the herbicidal composition of the present invention to the surface water of a paddy field flooded with water where weeds grow or are likely to grow. Methods of applying the herbicidal composition of the present invention include a uniform area application method and a selective spot application method. Even when the herbicidal composition of the present invention is sprayed in small amounts in an area where weeds do not grow or where there is no risk of weeds growing due to drift, transpiration, etc., it is included in the spot application as long as it is not a uniform area application. Furthermore, spot treatment does not necessarily mean that all areas where weeds grow or are likely to grow in a continuous area where useful plants are cultivated are selectively treated. That is, even if part of the cultivation area is treated over an entire area, or even if some areas where weeds grow or are likely to grow are not treated with the herbicidal composition of the present invention, spot treatment is still considered to be a spot treatment as long as there are areas in the continuous area where useful plants are cultivated that have been spot-treated. Spot treatment may be carried out while avoiding useful plants, or may be carried out based only on the location of weeds, regardless of the location of useful plants.

[0083] Specific examples of spot treatment methods are given below. Spot treatment may be performed by visually spraying the herbicidal composition of the present invention using a handheld nozzle or robotic arm nozzle while an applicator is walking or riding on a ground-based or flying device in a cultivation area of ​​useful plants. Furthermore, spot treatment may be performed by mapping the area where weeds are growing or are likely to grow in advance and spraying the compound of the present invention or the herbicidal composition of the present invention containing the compound of the present invention and one or more compounds selected from the compound of the present invention and the present component based on the map information. In spraying based on map information, in addition to the above-mentioned methods, spot treatment may be performed by automatically or manually opening and closing the boom nozzle or robotic arm nozzle while the sprayer is traveling or flying, based on the sprayer's position information (obtained by GPS, etc.) and the map information. The map information may be created based on image information captured by a manned or unmanned flying object, or may be created visually by an observer walking on the ground, riding on a ground-based or flying device, or by an observer riding on a flying device. Furthermore, a traveling or flying sprayer may be equipped with a function for detecting areas where weeds are growing or are likely to grow, and spot treatment may be performed using the boom or robot arm while performing real-time mapping. Such techniques are described in patent documents (e.g., WO 2018 / 001893, WO 2018 / 036909) and non-patent documents (e.g., Crop Protection 26, 270-277, Weed Technology 17, 711-717, Applied Engineering in Agriculture 30, 143-152). These technologies are a form of emerging agriculture known as precision agriculture, smart agriculture, or digital agriculture, and the uneven application pattern caused by the spot treatment is also referred to as VRA (Variable Rate Application) in the emerging agriculture field. Locations where weeds are likely to grow may be estimated based on the fact that the weeds formed vegetation patches in past growing seasons, or may be estimated from the distribution of buried seeds in the soil.The distribution of seed banks can be investigated by soil sampling or estimated by remote sensing.

[0084] The present invention will be explained in more detail below with reference to Production Examples, Formulation Examples, Test Examples, etc., but the present invention is not limited to these examples. First, production examples of the compounds of the present invention and their production intermediates will be shown.

[0085] Reference manufacturing example 1

[0086] STEP 1: Preparation of 4-trifluoromethoxybenzenediazonium chloride aqueous solution (hereinafter referred to as solution A) 17.7 g of 4-(trifluoromethoxy)aniline, 80 mL of water, and 80 mL of 3N hydrochloric acid were mixed at room temperature and then cooled in an ice bath. To the resulting aqueous solution, an aqueous sodium nitrite solution (6.9 g of sodium nitrite / 50 mL of water) was added dropwise under ice cooling, and the mixture was stirred for 10 minutes to obtain solution A.

[0087] STEP 2: Diazo Coupling 12.6 g of 4-hydroxy-6-methyl-2H-pyran-2-one, 100 mL of water, and 25.4 g of sodium carbonate were mixed at room temperature, and then Solution A was added dropwise with stirring under ice cooling. After the dropwise addition was completed, the resulting slurry was gradually warmed to room temperature, and then an aqueous sodium thiosulfate solution was added and stirred at room temperature for 15 minutes. The target hydrazone compound was obtained by filtering the solid from the resulting slurry.

[0088] STEP 3: Pyridazinone Cyclization The hydrazone compound obtained in STEP 2 and 200 mL of 1N aqueous sodium hydroxide were mixed at room temperature and stirred under reflux for 1 hour. After cooling to room temperature, 3N hydrochloric acid was added. The precipitated solid was collected by filtration to obtain 26.8 g of Intermediate 1 represented by the following formula. Intermediate 1: 1 H-NMR (CDCl3) δ: 7.53-7.41 (4H, m), 6.91 (1H, s), 2.35 (3H, s).

[0089] Reference Production Example 2 25.1 g of Intermediate 1, 80 mL of DMF, 16.6 g of potassium carbonate, and 18.7 g of ethyl iodide were mixed at room temperature and stirred at 50°C for 3 hours. Methyl tert-butyl ether (hereinafter referred to as MTBE) and water were added to the obtained mixture, and the layers were separated. The obtained organic layer was dried over magnesium sulfate and concentrated under reduced pressure to obtain 13.7 g of Intermediate 2 represented by the following formula: Intermediate 2: 1 H-NMR (CDCl3) δ: 7.45-7.37 (4H, m), 6.59 (1H, s), 4.42 (2H, q), 2.18 (3H, s), 1.38 (3H, t).

[0090] Reference Production Example 3: 13.7 g of Intermediate 2, 7.48 g of N-bromosuccinimide, and 80 mL of acetonitrile were mixed at room temperature and stirred at 60°C for 2 hours. The solvent was removed under reduced pressure, and then ethyl acetate was added to the resulting residue, which was then washed successively with a mixed solution of aqueous sodium thiosulfate and saturated aqueous sodium hydrogencarbonate, water, and saturated brine. The resulting organic layer was dried over magnesium sulfate and concentrated under reduced pressure to obtain 17.3 g of Intermediate 3 represented by the following formula: Intermediate 3: 1 H-NMR (CDCl3) δ: 7.47-7.39 (4H, m), 4.43 (2H, q), 2.44 (3H, s), 1.38 (3H, t).

[0091] Production Example 1: 421 mg of intermediate 3,4-fluorobenzylboronic acid pinacol ester (354 mg), [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride (220 mg), tripotassium phosphate (531 mg), 1,2-dimethoxyethane (3 mL), and purified water (0.7 mL) were mixed at room temperature and then stirred at 70°C for 90 minutes. Saturated brine was added to the resulting mixture, and the mixture was extracted with methyl tert-butyl ether (MTBE). The resulting organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (hexane:ethyl acetate=1:1) to obtain 355 mg of Compound 1 of the present invention, which is represented by the following formula: Compound 1 of the present invention: 1H-NMR (CDCl3) δ: 7.42-7.34 (4H, m), 7.26-7.21 (2H, m), 7.00-6.93 (2H, m), 4.43 (2H, dt), 3.97 (2H, s), 2.16 (3H, s), 1.42-1.36 (3H, m).

[0092] Preparation Example 2: 5 mL of 1 M aqueous sodium hydroxide solution and 5 mL of ethanol were added to 217 mg of Compound 1 of the present invention, and the mixture was stirred at room temperature for 30 minutes. After ethanol was distilled off under reduced pressure, 4 mL of 3 M hydrochloric acid was added. The precipitated solid was collected by filtration to obtain 140 mg of Compound 2 of the present invention. Compound 2 of the present invention: 1 H-NMR (CDCl3) δ: 7.41-7.41 (4H, m), 7.25-7.18 (2H, m), 7.03-6.98 (2H, m), 4.06 (2H, s), 2.31 (3H, s).

[0093] Preparation Example 3: 421 mg of Intermediate 3, 151 mg of phenol, 39 mg of copper(I) iodide, 62 mg of N-butylimidazole, 977 mg of cesium carbonate, and 2 mL of DMF were mixed under a nitrogen gas atmosphere and stirred at 100°C for 6 hours. After cooling to room temperature, 2 mL of 1N aqueous sodium hydroxide was added to the resulting mixture and stirred at room temperature for 1 hour. The resulting mixture was partitioned between MTBE and water. 3N hydrochloric acid was added to the resulting aqueous layer, followed by extraction with chloroform. The resulting organic layer was dried over sodium sulfate and filtered, after which the solvent was distilled off under reduced pressure. The resulting residue was subjected to reverse-phase column chromatography (ODS column) (water:acetonitrile = 1:1) to obtain 90 mg of Compound 3 of the present invention represented by the following formula: Compound 3 of the present invention: 1 H-NMR (CDCl3) δ: 7.55-7.51 (2H, m), 7.47-7.45 (2H, m), 7.40-7.35 (2H, m), 7.19-7.15 (1H, m), 6.99-6.97 (2H, m), 2.39 (3H, s).

[0094] Reference Production Example 3A According to Reference Production Examples 1 to 3, intermediate 4 represented by the following formula was prepared. Intermediate 4: 1 H-NMR (CDCl3) δ: 7.56-7.53 (2H, m), 7.33-7.31 (2H, m), 4.43 (2H, q), 2.44 (3H, s), 1.38 (3H, t).

[0095] Production Example 4: 421 mg of intermediate 4,4-fluorobenzenethiol (141 mg), bis(dibenzylideneacetone)palladium (52 ​​mg), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (76 mg), diisopropylamine (258 mg), and 4-methyltetrahydropyran (3 mL) were stirred under a nitrogen gas atmosphere at 100° C. for 2 hours. After cooling to room temperature, the resulting mixture was subjected to silica gel column chromatography (hexane:ethyl acetate=1:1) to obtain 442 mg of the present invention compound 4 represented by the following formula. Compound 4 of the present invention: 1 H-NMR (CDCl3) δ: 7.55-7.51 (2H, m), 7.39-7.37 (2H, m), 7.32-7.30 (2H, m), 7.01-6.95 (2H, m), 4.39 (2H, q), 2.48 (3H, s), 1.35 (3H, t).

[0096] Preparation Example 5: 70 mg of compound 4 of the present invention, 96 mg of m-chloroperbenzoic acid, and 1 mL of chloroform were mixed under ice-cooling and stirred for 2 hours. The resulting mixture was diluted with chloroform and washed with a saturated aqueous solution of sodium sulfite and a saturated aqueous solution of sodium bicarbonate. The resulting organic layer was dried over sodium sulfate and filtered, and the solvent was then distilled off under reduced pressure to obtain 76 mg of compound 5 of the present invention represented by the following formula: Compound 5 of the present invention: 1 H-NMR (CDCl3) δ: 8.18-8.15 (2H, m), 7.56-7.53 (2H, m), 7.31-7.29 (2H, m), 7.23-7.19 (2H, m), 4.34 (2H, q), 2.73 (3H, s), 1.31 (3H, t).

[0097] Reference Production Example 4-1 Intermediate 5 represented by the following formula was produced according to Reference Production Examples 1 and 2. Intermediate 5: 1 H-NMR (CDCl3) δ: 7.54-7.52 (2H, m), 7.34-7.30 (2H, m), 6.59 (1H, s), 4.42 (2H, q), 2.19 (3H, s), 1.39 (3H, t).

[0098] Reference Production Example 4-2 9.55 g of Intermediate 5, 8.3 g of silver mesylate, 10.4 g of iodine, and 100 mL of acetonitrile were mixed and stirred at room temperature for 2 hours. The resulting mixture was filtered through Celite (registered trademark), and then an aqueous sodium thiosulfate solution was added to the filtrate, followed by separation with chloroform. The resulting organic layer was dried over sodium sulfate and filtered, after which the solvent was distilled off under reduced pressure. 50 mL of a 1N aqueous sodium hydroxide solution was added to the resulting residue, and the mixture was stirred at room temperature for 1 hour. 3N hydrochloric acid was then added, and the precipitated solid was collected by filtration, yielding 11.8 g of Intermediate 6 represented by the following formula: Intermediate 6: 1 H-NMR (CDCl3) δ: 7.60-7.57 (2H, m), 7.35-7.31 (2H, m), 2.67 (3H, s).

[0099] Reference Production Example 5: 4.0 g of Intermediate 6, 7 mL of di-tert-butyl dicarbonate, 125 mg of 4-dimethylaminopyridine, and 20 mL of tert-butyl alcohol were mixed and stirred under reflux for 6 hours. After cooling to room temperature, chloroform was added and the mixture was washed with a saturated aqueous solution of sodium bicarbonate. The resulting organic layer was dried over sodium sulfate and filtered, and the solvent was then distilled off under reduced pressure to obtain 3.50 g of Intermediate 7, which is represented by the following formula: Intermediate 7: 1 H-NMR (CDCl3) δ: 7.55-7.51 (2H, m), 7.33-7.28 (2H, m), 2.53 (3H, s), 1.60 (9H, s).

[0100] Preparation Example 6: 500 mg of intermediate 7, 292 mg of 4-fluoroaniline, 97 mg of bis(dibenzylideneacetone)palladium, 65 mg of 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene, 1.1 g of cesium carbonate, and 3 mL of 4-methyltetrahydropyran were mixed under a nitrogen gas atmosphere and stirred at 100°C for 2.5 hours. After cooling to room temperature, the resulting mixture was subjected to short-pad column chromatography (hexane:ethyl acetate=1:1). The resulting crude product was dissolved in 1 mL of chloroform, and 1 mL of trifluoroacetic acid was added and stirred at room temperature for 1 hour. The solvent was distilled off under reduced pressure, and the resulting residue was dissolved in 2 mL of DMF. 96 mg of iodoethane and an excess amount of sodium bicarbonate were added, and the mixture was stirred at 80°C for 2 hours. The resulting mixture was subjected to silica gel column chromatography (hexane:ethyl acetate=1:1) to obtain 112 mg of the present invention compound 6 represented by the following formula: Compound 6 of the present invention: 1 H-NMR (CDCl3) δ: 7.53-7.50 (2H, m), 7.38-7.32 (2H, m), 6.99-6.97 (2H, m), 6.99 (1H, br s), 6.87-6.83 (2H, m), 4.43 (2H, q), 1.91 (3H, s), 1.41 (3H, t).

[0101] Reference Production Example 6 According to Reference Production Examples 1 to 3, intermediate 8 represented by the following formula was prepared. Intermediate 8: 1 H-NMR (CDCl3) δ: 7.55-7.52 (2H, m), 7.33-7.30 (2H, m), 2.42 (3H, s), 1.60 (9H, s).

[0102] Preparation Example 7: 300 mg of Intermediate 8, 102 mg of pyrazole, 28.5 mg of copper(I) iodide, 53 mg of trans-1,2-cyclohexanediamine, 1.1 g of cesium carbonate, and 1 mL of DMF were mixed under a nitrogen gas atmosphere and stirred at 100°C for 6 hours. After cooling to room temperature, the resulting mixture was diluted with chloroform and washed with water. The resulting organic layer was dried over sodium sulfate and filtered, and the solvent was evaporated under reduced pressure. 5 mL of chloroform and 5 mL of trifluoroacetic acid were added to the resulting residue, and the mixture was stirred at room temperature for 1 hour. The solvent was evaporated under reduced pressure, and the resulting residue was dissolved in 2 mL of DMF. 241 mg of iodoethane and an excess amount of sodium bicarbonate were added, and the mixture was stirred at 80°C for 2 hours. The resulting mixture was subjected to silica gel column chromatography (hexane:ethyl acetate=1:1) to obtain 53 mg of Compound 7 of the present invention, represented by the following formula: Compound 7 of the present invention: 1 H-NMR (CDCl3) δ: 7.93 (1H, d), 7.72 (1H, d), 7.55-7.53 (2H, m), 7.40-7.37 (2H, m), 6.47 (1H, dd), 4.42 (2H, q), 2.22 (3H, s), 1.39 (3H, t).

[0103] Reference Production Example 7 5.0 g of 3,4-difluorophenol, 5.0 g of cesium carbonate, 4.80 g of 3-chloroacetylacetone, and 250 mL of acetone were mixed and stirred under reflux for 8 hours. After cooling to room temperature, the resulting mixture was filtered through Celite, and the solvent was then distilled off under reduced pressure. The resulting residue was subjected to silica gel column chromatography (hexane:ethyl acetate=1:1) to obtain 4.80 g of intermediate 9 represented by the following formula: Intermediate 9: 1 H-NMR (CDCl3) δ: 14.39 (1H, s), 7.16-7.05 (1H, m), 6.82-6.73 (1H, m), 6.69-6.60 (1H, m), 2.03 (6H, s).

[0104] Reference Preparation Example 8: A THF solution (20 mL) of 1.82 g of intermediate 9 was cooled to -60°C, and 1.16 M sodium bis(trimethylsilyl)amide / THF solution (20.7 mL) was added dropwise. The resulting mixture was warmed to 0°C and stirred for 5 minutes, then cooled again to -60°C, and 792 μL of dimethyl carbonate was added. The resulting mixture was stirred at room temperature for 30 minutes, then mixed with 3 N hydrochloric acid and extracted with ethyl acetate. The resulting organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was distilled off under reduced pressure. 100 mL of toluene and 5.11 mL of diazabicycloundecene were added to the resulting residue, and the mixture was stirred at 100°C for 3 hours. After cooling to room temperature, 3 N hydrochloric acid was added to the resulting mixture, and the mixture was extracted with ethyl acetate. The resulting organic layer was dried over sodium sulfate, and the solvent was distilled off under reduced pressure, yielding 1.71 g of intermediate 10 represented by the following formula: Intermediate 10: 1 H-NMR (DMSO-d6) δ: 12.35-12.18 (1H, m), 7.44-7.33 (1H, m), 7.24-7.13 (1H, m), 6.88-6.77 (1H, m), 5.43-5.33 (1H, m), 2.13-2.06 (3H, m).

[0105] Production Example 8

[0106] STEP 1: Preparation of 4-chlorobenzenediazonium chloride aqueous solution (hereinafter referred to as solution B) 381 mg of 4-chloroaniline and 2.4 mL of 3N hydrochloric acid were mixed at room temperature and then cooled in an ice bath. To the resulting aqueous solution, an aqueous sodium nitrite solution (207 mg of sodium nitrite / 3.0 mL of water) was added dropwise under ice cooling, and the mixture was stirred for 10 minutes to obtain solution B.

[0107] STEP 2: Diazo Coupling 381 mg of Intermediate 10, 2.4 mL of water, and 763 mg of sodium carbonate were mixed at room temperature, and then Solution B was added dropwise with stirring under ice cooling. After the dropwise addition was completed, the resulting slurry was gradually warmed to room temperature, and then an aqueous sodium thiosulfate solution was added and stirred at room temperature for 15 minutes. The resulting mixture was extracted with chloroform. The resulting organic layer was dried over sodium sulfate and filtered, and the solvent was then distilled off under reduced pressure to obtain the desired hydrazone compound.

[0108] STEP 3: Pyridazinone Cyclization The hydrazone compound obtained in STEP 2, 10 mL of THF, and 10 mL of 1N aqueous sodium hydroxide were mixed at room temperature and stirred under reflux for 6 hours. After cooling to room temperature, 3N hydrochloric acid was added and the mixture was extracted with ethyl acetate. The resulting organic layer was dried over sodium sulfate, filtered, and the solvent was distilled off under reduced pressure. The resulting residue was recrystallized from a mixture of hexane and ethyl acetate to obtain 174 mg of Compound 97 of the present invention represented by the following formula: Compound 97 of the present invention: 1 H-NMR (CDCl3) δ: 7.63-7.54 (2H, m), 7.43-7.35 (2H, m), 7.21-7.09 (1H, m), 6.91-6.78 (1H, m), 6.74-6.62 (1H, m), 2.39 (3H, s).

[0109] Preparation Example 9: 100 mg of the present invention compound 97 and 1 mL of THF were mixed and stirred at -78°C. 0.51 mL of a sodium bis(trimethylsilyl)amide THF solution (1.9 mol / L) was added dropwise to the resulting mixture, followed by stirring at 0°C for 10 minutes. The resulting mixture was cooled to -78°C again, and 32 μL of iodomethane was added dropwise. The resulting mixture was warmed to room temperature, 3N hydrochloric acid was added, and the mixture was extracted with ethyl acetate. The resulting organic layer was dried over sodium sulfate and filtered, and the solvent was distilled off under reduced pressure. The resulting residue was recrystallized from hexane / ethyl acetate to obtain 40 mg of the present invention compound 98 represented by the following formula: Compound 98 of the present invention: 1H-NMR (CDCl3) δ: 7.56-7.50 (2H, m), 7.48-7.41 (2H, m), 7.18-7.09 (1H, m), 6.93-6.86 (1H, m), 6.76-6.69 (1H, m), 2.73 (2H, q), 1.12 (3H, t).

[0110] Reference Preparation Example 9: 7.40 g of Intermediate 4, 5.15 g of 1-ethoxyethene-2-boronic acid pinacol ester, 731 mg of [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride, 5.51 g of potassium phosphate, 10 mL of water, and 40 mL of 4-methyltetrahydropyran were mixed and stirred at 80°C under a nitrogen atmosphere. The resulting mixture was cooled to room temperature and washed with brine. The resulting organic layer was dried over sodium sulfate and filtered, and the solvent was then distilled off under reduced pressure. The resulting residue was recrystallized from a mixture of hexane and ethyl acetate to obtain 6.66 g of Intermediate 11 represented by the following formula: Intermediate 11: 1 H-NMR (CDCl3) δ: 8.56 (1H, d), 7.53-7.48 (2H, m), 7.32-7.27 (2H, m), 5.72 (1H, d), 4.43 (2H, q), 4.00 (2H, q), 2.23 (3H, s), 1.39 (3H, t), 1.33 (3H, t).

[0111] Preparation Example 10: According to the following scheme, compound 99 of the present invention was prepared from intermediate 11 via intermediates 12, 13, and 14. In the following scheme, a compound marked with (12) represents intermediate 12, a compound marked with (13) represents intermediate 13, and a compound marked with (14) represents intermediate 14.

[0112] STEP 1: Ozonolysis and reduction 5.66 g of intermediate 11, 50 mL of ethyl acetate, and 5 mL of pyridine were mixed. The resulting mixture was cooled to -78°C, and ozone was bubbled through for 15 minutes while stirring. Nitrogen gas was bubbled through for 5 minutes, and then 816 mg of sodium borohydride was added, and the reaction solution was heated to 0°C. A saturated aqueous solution of ammonium chloride was added, and the resulting mixture was separated and washed with brine. The resulting organic layer was dried over sodium sulfate and filtered, and the solvent was then distilled off under reduced pressure to obtain 5.32 g of a crude product containing intermediate 12.

[0113] STEP 2: Chlorination 1.0 g of the crude product obtained in STEP 1 was dissolved in 10 mL of chloroform, and 357 μL of thionyl chloride was added dropwise to the resulting solution under ice-cooling. The resulting mixture was stirred at room temperature for 3 hours, then added to ice-cooled saturated aqueous sodium bicarbonate solution and extracted with chloroform. The resulting organic layer was dried over sodium sulfate, filtered, and the solvent was evaporated under reduced pressure. The resulting residue was subjected to short-pad column chromatography (hexane:ethyl acetate=1:1) to yield 340 mg of a crude product containing intermediate 13.

[0114] STEP 3: Iodination (Preparation of Solution C) The entire amount of the crude product obtained in STEP 2 was dissolved in 5 mL of acetone, 150 mg of sodium iodide was added, and the mixture was stirred at room temperature for 30 minutes. The resulting mixture was filtered, and the solvent was distilled off under reduced pressure. The entire amount of the residue obtained was dissolved in 5 mL of acetonitrile to obtain Solution C containing Intermediate 14.

[0115] STEP 4: Introduction of a pyrazolyl group and ester hydrolysis 153 mg of 4-chloropyrazole, 355 mg of cesium carbonate, and 5 mL of acetonitrile were mixed and stirred at room temperature for 30 minutes. Solution C prepared in STEP 3 was added dropwise to the resulting mixture, and the mixture was stirred at room temperature for 4 hours. 1 mL of 1N aqueous sodium hydroxide was added, and the mixture was stirred at room temperature for 1 hour. After that, 3N hydrochloric acid was added and the mixture was extracted with ethyl acetate. The resulting organic layer was dried over sodium sulfate and filtered, and the solvent was distilled off under reduced pressure. The resulting residue was subjected to reverse phase column chromatography (ODS column) (water:acetonitrile = 1:1) to obtain 160 mg of the present invention compound 99 represented by the following formula. This compound 99: 1 H-NMR (CDCl3) δ: 7.71 (1H, br s), 7.58-7.54 (2H, m), 7.38 (1H, br s), 7.35-7.29 (2H, m), 5.33 (2H, s), 2.60 (3H, s).

[0116] Production Example 8 The production method and the methods described in the Production Examples are accurate to the production of the compounds and their physical properties are shown below.

[0117] This compound 8: 1 ¹H-NMR (CDCl₃) δ: 7.44–7.37 (4H, m), 7.34–7.30 (2H, m), 7.28–7.23 (3H, m), 4.10 (2H, s), 2.31 (3H, s). Compound 9 of this invention: 1 ¹H-NMR (CDCl₃) δ: 7.41–7.34 (4H, m), 7.29–7.27 (4H, m), 7.24–7.17 (1H, m), 4.43 (2H, q), 4.02 (2H, s), 2.15 (3H, s), 1.39 (3H, t). Compound 10 of this invention: 1 H-NMR (CDCl3) δ: 7.52-7.30 (9H, m), 6.13 (1H, s), 5.41 (1H, s), 2.23 (3H, s).

[0118] Compound 11 of this invention: 1 ¹H-NMR (CDCl₃) δ: 7.45–7.36 (4H, m), 7.26–7.20 (1H, m), 7.06 (1H, d), 6.97 (1H, d), 6.93–6.87 (1H, m), 4.43 (2H, q), 4.01 (2H, s), 2.16 (3H, s), 1.39 (3H, t). Compound 12 of this invention: 1¹H-NMR (CDCl₃) δ: 7.47–7.35 (5H, m), 7.22–7.16 (1H, m), 7.08–6.98 (2H, m), 4.42 (2H, q), 4.02 (2H, s), 2.20 (3H, s), 1.38 (3H, t). Compound 13 of this invention: 1 H-NMR (CDCl3) δ: 7.64 (1H, d), 7.53 (1H, d), 7.25-7.20 (3H, m), 7.03-6.99 (2H, m), 4.05 (2H, s), 2.32 (3H, s).

[0119] This compound 14: 1 ¹H-NMR (CDCl₃) δ: 7.42–7.22 (9H, m), 4.94 (1H, q), 2.08 (3H, s), 1.73 (3H, d). Compound 15 of this invention: 1 ¹H-NMR (CDCl₃) δ: 7.54–7.49 (2H, m), 7.34–7.28 (4H, m), 7.26–7.22 (3H, m), 4.10 (2H, s), 2.30 (3H, s). Compound 16 of this invention: 1 H-NMR (CDCl3) δ: 7.44-7.36 (4H, m), 7.17-7.10 (4H, m), 4.06 (2H, s), 2.32 (3H, s), 2.31 (3H, s).

[0120] This compound 17: 1 ¹H-NMR (CDCl₃) δ: 7.45–7.38 (4H, m), 7.22–7.18 (1H, m), 7.07–7.00 (3H, m), 4.06 (2H, s), 2.33 (3H, s), 2.31 (3H, s). Compound 18 of this invention: 1 ¹H-NMR (CDCl₃) δ: 7.51–7.46 (2H, m), 7.30–7.24 (6H, m), 7.23–7.17 (1H, m), 4.43 (2H, q), 4.01 (2H, s), 2.14 (3H, s), 1.39 (3H, t). Compound 19 of this invention: 1H-NMR (CDCl3) δ: 7.50-7.47 (2H, m), 7.42-7.36 (2H, m), 7.22 (1H, d), 7.19-7.07 (2H, m), 6.75 (1H, d), 4.05 (2H, s), 2.41 (3H, s), 2.21 (3H, s).

[0121] This compound 20: 1 ¹H-NMR (CDCl₃) δ: 7.41–7.34 (4H, m), 7.18 (2H, d), 7.08 (2H, d), 4.43 (2H, q), 3.97 (2H, s), 2.30 (3H, s), 2.15 (3H, s), 1.39 (3H, t). Compound 21 of this invention: 1 ¹H-NMR (CDCl₃) δ: 7.41–7.33 (4H, m), 7.19–7.13 (1H, m), 7.09–7.00 (3H, m), 4.44 (2H, q), 3.98 (2H, s), 2.31 (3H, s), 2.15 (3H, s), 1.39 (3H, t). Compound 22 of this invention: 1 H-NMR (CDCl3) δ: 7.45-7.35 (4H, m), 7.17-7.06 (3H, m), 6.87-6.84 (1H, m), 4.43 (2H, q), 3.97 (2H, s), 2.39 (3H, s), 2.06 (3H, s), 1.39 (3H, t).

[0122] This compound 23: 1 ¹H-NMR (CDCl₃) δ: 7.45 (2H, d), 7.39 (2H, d), 7.32–7.25 (1H, m), 7.03 (1H, d), 6.99–6.92 (2H, m), 4.09 (2H, s), 2.31 (3H, s). Compound 24 of this invention: 1¹H-NMR (CDCl₃) δ: 7.44–7.36 (5H, m), 7.28–7.22 (1H, m), 7.11 (1H, ddd), 7.08–7.03 (1H, m), 4.10 (2H, s), 2.36 (3H, s). Compound 25 of this invention: 1 H-NMR (CDCl3) δ: 7.54-7.50 (2H, m), 7.34-7.29 (2H, m), 7.25-7.20 (2H, m), 7.03-6.97 (2H, m), 4.05 (2H, s), 2.30 (3H, s).

[0123] This compound 26: 1 ¹H-NMR (CDCl₃) δ: 7.51–7.47 (2H, m), 7.30–7.22 (4H, m), 6.98–6.92 (2H, m), 4.43 (2H, q), 3.97 (2H, s), 2.15 (3H, s), 1.39 (3H, t). Compound 27 of this invention: 1 ¹H-NMR (CDCl₃) δ: 7.53–7.48 (2H, m), 7.48–7.41 (1H, m), 7.30–7.27 (2H, m), 6.83–6.73 (2H, m), 4.42 (2H, q), 3.95 (2H, s), 2.19 (3H, s), 1.38 (3H, t). Compound 28 of this invention: 1 H-NMR (CDCl3) δ: 7.50 (2H, d), 7.28 (2H, d), 7.25-6.96 (3H, m), 4.43 (2H, q), 3.95 (2H, s), 2.15 (3H, s), 1.39 (3H, t).

[0124] This compound 29: 1 ¹H-NMR (CDCl₃) δ: 7.55–7.48 (4H, m), 7.40 (2H, d), 7.30–7.26 (2H, m), 4.43 (2H, q), 4.06 (2H, s), 2.15 (3H, s), 1.39 (3H, t). Compound 30 of this invention: 1¹H-NMR (CDCl₃) δ: 7.59–7.52 (4H, m), 7.38 (2H, d), 7.33–7.28 (2H, m), 4.15 (2H, s), 2.30 (3H, s). Compound 31 of this invention: 1 H-NMR (CDCl3) δ: 7.53-7.49 (2H, m), 7.38-7.28 (7H, m), 6.00 (1H, d), 5.33 (1H, d), 4.41 (2H, q), 2.06 (3H, s), 1.37 (3H, t).

[0125] This compound 32: 1 ¹H-NMR (CDCl₃) δ: 7.53–7.48 (2H, m), 7.30–7.27 (2H, m), 7.23 (1H, dd), 7.07–7.03 (1H, m), 6.99–6.94 (1H, m), 6.93–6.86 (1H, m), 4.43 (2H, q), 4.00 (2H, s), 2.14 (3H, s), 1.39 (3H, t). Compound 33 of this invention: 1 ¹H-NMR (CDCl₃) δ: 7.54 (2H, d), 7.31 (2H, d), 7.14–7.06 (2H, m), 7.02–6.94 (1H, m), 4.04 (2H, s), 2.31 (3H, s). Compound 34 of this invention: 1 H-NMR (CDCl3) δ: 7.57-7.52 (2H, m), 7.43-7.36 (1H, m), 7.33-7.29 (2H, m), 6.87-6.78 (2H, m), 4.04 (2H, s), 2.35 (3H, s).

[0126] This compound 35: 1 ¹H-NMR (CDCl₃) δ: 7.63 (¹H, d), 7.52 (¹H, d), 7.34–7.30 (²H, m), 7.28–7.21 (⁴H, m), 4.09 (²H, s), 2.32 (³H, s). Compound 36 of this invention: 1¹H-NMR (CDCl₃) δ: 7.56–7.51 (2H, m), 7.39–7.33 (1H, m), 7.33–7.29 (2H, m), 7.26–7.21 (1H, m), 7.13–7.03 (2H, m), 4.10 (2H, s), 2.34 (3H, s). Compound 37 of this invention: 1 H-NMR (CDCl3) δ: 7.59 (1H, d), 7.48 (1H, d), 7.30-7.26 (4H, m), 7.23-7.18 (2H, m), 4.43 (2H, q), 4.01 (2H, s), 2.17 (3H, s), 1.39 (3H, t).

[0127] This compound 38: 1 ¹H-NMR (CDCl₃) δ: 7.54–7.51 (2H, m), 7.34–7.31 (2H, m), 7.25–7.22 (2H, m), 7.04–6.98 (2H, m), 4.06 (2H, s), 2.26 (3H, s). Compound 39 of this invention: 1 ¹H-NMR (CDCl₃) δ: 7.56–7.50 (2H, m), 7.33–7.26 (3H, m), 7.03 (1H, d), 6.99–6.92 (2H, m), 4.09 (2H, s), 2.30 (3H, s). Compound 40 of this invention: 1 H-NMR (CDCl3) δ: 7.60 (1H, d), 7.48 (1H, d), 7.26-7.18 (3H, m), 7.01-6.93 (2H, m), 4.43 (2H, q), 3.96 (2H, s), 2.17 (3H, s), 1.39 (3H, t).

[0128] This compound 41: 1¹H-NMR (CDCl₃) δ: 7.52–7.48 (2H, m), 7.44–7.40 (1H, m), 7.30–7.27 (2H, m), 7.22–7.14 (1H, m), 7.09–6.97 (2H, m), 4.42 (2H, q), 4.02 (2H, s), 2.18 (3H, s), 1.38 (3H, t). Compound 42 of this invention: 1 ¹H-NMR (CDCl₃) δ: 7.34–7.27 (6H, m), 7.24–7.16 (3H, m), 4.43 (2H, q), 4.01 (2H, s), 2.13 (3H, s), 1.39 (3H, t). Compound 43 of this invention: 1 H-NMR (CDCl3) δ: 7.52-7.47 (2H, m), 7.29-7.20 (6H, m), 4.43 (2H, q), 3.97 (2H, s), 2.13 (3H, s), 1.39 (3H, t).

[0129] This compound 44: 1 ¹H-NMR (CDCl₃) δ: 7.38–7.33 (2H, m), 7.26–7.20 (4H, m), 7.04–6.97 (2H, m), 4.06 (2H, s), 2.29 (3H, s). Compound 45 of this invention: 1 ¹H-NMR (CDCl₃) δ: 7.36–7.30 (4H, m), 7.26–7.21 (5H, m), 4.10 (2H, s), 2.29 (3H, s). Compound 46 of this invention: 1 H-NMR (CDCl3) δ: 7.34-7.29 (2H, m), 7.25-7.17 (4H, m), 6.98-6.93 (2H, m), 4.43 (2H, q), 3.96 (2H, s), 2.14 (3H, s), 1.39 (3H, t).

[0130] This compound 47: 1¹H-NMR (CDCl₃) δ: 7.56–7.51 (2H, m), 7.32–7.27 (4H, m), 7.21–7.17 (2H, m), 4.05 (2H, s), 2.29 (3H, s). Compound 48 of this invention: 1 ¹H-NMR (CDCl₃) δ: 7.40–7.29 (2H, m), 7.25–7.19 (2H, m), 7.19–7.13 (1H, m), 7.04–6.97 (2H, m), 4.05 (2H, s), 2.31 (3H, s). Compound 49 of this invention: 1 H-NMR (CDCl3) δ: 7.37-7.28 (1H, m), 7.26-7.20 (3H, m), 7.15-7.08 (1H, m), 6.99-6.92 (2H, m), 4.43 (2H, q), 3.96 (2H, s), 2.16 (3H, s), 1.39 (3H, t).

[0131] This compound 50: 1 ¹H-NMR (CDCl₃) δ: 7.39–7.23 (7H, m), 7.18–7.13 (1H, m), 4.09 (2H, s), 2.31 (3H, s). Compound 51 of this invention: 1 ¹H-NMR (CDCl₃) δ: 7.36–7.18 (7H, m), 7.13–7.09 (1H, m), 4.43 (2H, q), 4.01 (2H, s), 2.16 (3H, s), 1.39 (3H, t). Compound 52 of this invention: 1 H-NMR (CDCl3) δ: 7.60-7.56 (2H, m), 7.53-7.49 (2H, m), 7.41-7.37 (2H, m), 7.29-7.27 (2H, m), 2.20 (3H, s).

[0132] This compound 53: 1 ¹H-NMR (CDCl₃) δ: 7.59–7.46 (5H, m), 7.43–7.38 (2H, m), 7.33–7.30 (2H, m), 2.20 (3H, s). Compound 54 of this invention: 1¹H-NMR (CDCl₃) δ: 7.55-7.51 (2H, m), 7.39-7.36 (2H, m), 7.25-7.23 (2H, m), 7.00-6.96 (2H, m), 4.42 (2H, q), 3.84 (3H, s), 2.08 (3H, s), 1.38 (3H, t)... Compound 55 of this invention: 1 H-NMR (CDCl3) δ: 7.50-7.47 (2H, m), 7.46-7.43 (2H, m), 7.41-7.36 (3H, m), 7.30-7.28 (2H, m), 4.42 (2H, q), 2.07 (3H, s), 1.37 (3H, t).

[0133] This compound 56: 1 ¹H-NMR (CDCl₃) δ: 7.56–7.43 (7H, m), 7.33–7.30 (2H, m), 2.21 (3H, s). Compound 57 of this invention: 1 ¹H-NMR (CDCl₃) δ: 7.50–7.46 (2H, m), 7.40 (2H, d), 7.33 (1H, t), 7.19 (1H, d), 7.12 (1H, s), 7.06 (1H, d), 4.42 (2H, q), 2.38 (3H, s), 2.06 (3H, s), 1.37 (3H, t). Compound 58 of this invention: 1 H-NMR (CDCl3) δ: 7.49-7.46 (2H, m), 7.42-7.37 (2H, m), 7.26-7.23 (2H, m), 7.20-7.16 (2H, m), 4.42 (2H, q), 2.38 (3H, s), 2.07 (3H, s), 1.37 (3H, t).

[0134] This compound 59: 1 ¹H-NMR (CDCl₃) δ: 7.55–7.49 (2H, m), 7.43 (2H, d), 7.34 (2H, d), 7.21 (2H, d), 2.42 (3H, s), 2.22 (3H, s). Compound 60 of this invention: 1¹H-NMR (CDCl₃) δ: 7.55-7.51 (2H, m), 7.49-7.41 (3H, m), 7.24-7.20 (1H, m), 7.14-7.09 (1H, m), 7.07-7.04 (1H, m), 3.83 (3H, s), 2.13 (3H, s). Compound 61 of this invention: 1 H-NMR (CDCl3) δ: 7.51-7.46 (2H, m), 7.43-7.39 (2H, m), 7.31-7.27 (2H, m), 7.17-7.12 (2H, m), 4.43 (2H, q), 2.07 (3H, s), 1.38 (3H, t).

[0135] This compound 62: 1 ¹H-NMR (CDCl₃) δ: 7.53–7.48 (2H, m), 7.42–7.34 (3H, m), 7.21 (1H, dd), 7.04 (1H, dd), 6.99–6.96 (1H, m), 4.45–4.38 (2H, m), 3.79 (3H, s), 1.98 (3H, s), 1.37 (3H, t). Compound 63 of this invention: 1 ¹H-NMR (CDCl₃) δ: 7.55–7.49 (2H, m), 7.45–7.40 (3H, m), 7.29 (1H, d), 7.13–7.07 (2H, m), 2.42 (3H, s), 2.20 (3H, s). Compound 64 of this invention: 1 H-NMR (CDCl3) δ: 7.59-7.54 (2H, m), 7.42-7.38 (2H, m), 7.29-7.24 (2H, m), 7.06-7.02 (2H, m), 3.87 (3H, s), 2.22 (3H, s).

[0136] This compound 65: 1 ¹H-NMR (CDCl₃) δ: 7.55–7.50 (2H, m), 7.47–7.42 (2H, m), 7.42–7.28 (3H, m), 7.11 (1H, d), 2.19 (3H, s), 2.10 (3H, s). Compound 66 of this invention: 1¹H-NMR (CDCl₃) δ: 7.52–7.47 (2H, m), 7.43–7.38 (2H, m), 7.32–7.28 (2H, m), 7.28–7.22 (1H, m), 7.09–7.06 (1H, m), 4.42 (2H, q), 2.18 (3H, s), 1.94 (3H, s), 1.38 (3H, t). Compound 67 of this invention: 1 H-NMR (CDCl3) δ: 7.54-7.50 (2H, m), 7.44 (2H, d), 7.34-7.30 (2H, m), 7.26-7.20 (2H, m), 2.22 (3H, s).

[0137] This compound 68: 1 ¹H-NMR (CDCl₃) δ: 7.55–7.51 (2H, m), 7.47–7.41 (2H, m), 7.40–7.35 (3H, m), 7.30–7.27 (2H, m), 4.42 (2H, q), 2.06 (3H, s), 1.37 (3H, t). Compound 69 of this invention: 1 ¹H-NMR (CDCl₃) δ: 7.52–7.28 (9H, m), 6.01 (1H, s), 5.34 (1H, s), 4.42 (2H, q), 2.07 (3H, s), 1.38 (3H, t). Compound 70 of this invention: 1 H-NMR (CDCl3) δ: 7.54-7.53 (2H, m), 7.39-7.37 (2H, m), 7.26-7.23 (2H, m), 7.20-7.18 (2H, m), 4.42 (2H, q), 2.39 (3H, s), 2.06 (3H, s), 1.36 (3H, t).

[0138] This compound 71: 1¹H-NMR (CDCl₃) δ: 7.56-7.53 (2H, m), 7.39-7.35 (4H, m), 7.26-7.22 (1H, m), 7.19-7.15 (1H, m), 4.47-4.39 (2H, m), 2.06-2.05 (3H, m), 1.40-1.38 (3H, m). Compound 72 of this invention: 1 ¹H-NMR (CDCl₃) δ: 7.56–7.53 (2H, m), 7.45–7.36 (3H, m), 7.11–7.00 (3H, m), 4.43 (2H, q), 2.06 (3H, s), 1.38 (3H, t). Compound 73 of this invention: 1 H-NMR (CDCl3) δ: 7.67-7.51 (6H, m), 7.41-7.35 (2H, m), 4.43 (2H, q), 2.07 (3H, s), 1.39 (3H, t).

[0139] This compound 74: 1 ¹H-NMR (CDCl₃) δ: 7.56–7.50 (4H, m), 7.37–7.35 (2H, m), 6.58 (1H, dd), 4.44 (2H, q), 2.46 (3H, s), 1.39 (3H, t). Compound 75 of this invention: 1 ¹H-NMR (CDCl₃) δ: 7.60–7.58 (2H, m), 7.43–7.31 (3H, m), 7.10–6.99 (2H, m), 2.21 (3H, d). Compound 76 of this invention: 1 H-NMR (CDCl3) δ: 7.59-7.53 (2H, m), 7.42-7.40 (2H, m), 7.36-7.32 (1H, m), 7.23-7.18 (1H, m), 7.09-7.07 (1H, m), 2.22 (3H, s).

[0140] This compound 77: 1¹H-NMR (CDCl₃) δ: 7.57–7.53 (2H, m), 7.38–7.36 (2H, m), 7.26–7.14 (2H, m), 7.05–7.00 (1H, m), 4.43 (2H, q), 2.05 (3H, s), 1.38 (3H, t). Compound 78 of this invention: 1 ¹H-NMR (CDCl₃) δ: 7.59–7.57 (2H, m), 7.51–7.47 (2H, m), 7.42–7.40 (2H, m), 7.34–7.33 (1H, m), 7.25–7.21 (1H, m), 2.21 (3H, s). Compound 79 of this invention: 1 H-NMR (CDCl3) δ: 7.59-7.57 (2H, m), 7.42-7.40 (2H, m), 7.34-7.31 (2H, m), 7.25-7.22 (3H, m), 2.21 (3H, s).

[0141] This compound 80: 1 ¹H-NMR (CDCl₃) δ: 7.56–7.53 (2H, m), 7.41–7.31 (5H, m), 7.20–7.18 (1H, m), 4.43 (2H, q), 2.05 (3H, s), 1.38 (3H, t). Compound 81 of this invention: 1 ¹H-NMR (CDCl₃) δ: 7.56–7.53 (2H, m), 7.39–7.37 (2H, m), 7.31–7.28 (2H, m), 7.17–7.14 (2H, m), 4.43 (2H, q), 2.07 (3H, s), 1.38 (3H, t). Compound 82 of this invention: 1 H-NMR (CDCl3) δ: 7.60-7.57 (2H, m), 7.53-7.49 (1H, m), 7.44-7.41 (2H, m), 7.40-7.31 (2H, m), 7.25-7.23 (2H, m), 2.21 (3H, d).

[0142] This compound 83: 1¹H-NMR (CDCl₃) δ: 7.59–7.56 (2H, m), 7.42–7.40 (2H, m), 7.35–7.33 (2H, m), 7.23–7.20 (2H, m), 2.43 (3H, s), 2.21 (3H, s). Compound 84 of this invention: 1 ¹H-NMR (CDCl₃) δ: 7.77–7.67 (2H, m), 7.60–7.53 (4H, m), 7.43–7.41 (2H, m), 2.21 (3H, s). Compound 85 of this invention: 1 H-NMR (CDCl3) δ: 7.59-7.57 (2H, m), 7.54-7.49 (1H, m), 7.42-7.40 (2H, m), 7.20-7.18 (1H, m), 7.10-7.07 (2H, m), 2.21 (3H, s).

[0143] This compound 86: 1 ¹H-NMR (CDCl₃) δ: 7.93 (¹H, s), 7.62–7.33 (⁵H, m), 2.50 (³H, s). Compound 87 of this invention: 1 ¹H-NMR (DMSO-D6) δ: 8.98 (2H, d), 7.78–7.74 (2H, m), 7.73–7.69 (2H, m), 7.57 (1H, t), 2.01 (3H, s). Compound 88 of this invention: 1 H-NMR (CDCl3) δ: 7.58-7.56 (2H, m), 7.41-7.39 (2H, m), 7.35-7.33 (2H, m), 7.05-7.01 (2H, m), 2.60 (3H, s).

[0144] This compound 89: 1 ¹H-NMR (CDCl₃) δ: 7.52–7.50 (2H, m), 7.37–7.35 (2H, m), 7.07–7.05 (2H, m), 7.00–6.99 (2H, m), 6.99 (¹H, br s), 1.92 (³H, s). Compound 90 of this invention: 1¹H-NMR (CDCl₃) δ: 7.55–7.51 (2H, m), 7.38–7.34 (2H, m), 6.94–6.92 (2H, m), 6.61–6.58 (2H, m), 4.41 (2H, q), 3.24 (3H, s), 2.06 (3H, s), 1.38 (3H, t). Compound 91 of this invention: 1 H-NMR (CDCl3) δ: 7.54-7.51 (2H, m), 7.41-7.38 (2H, m), 7.00-6.98 (2H, m), 6.68-6.62 (2H, m), 3.33 (3H, s), 2.19 (3H, s).

[0145] This compound 92: 1 ¹H-NMR (CDCl₃) δ: 7.98 (¹H, d), 7.81 (¹H, d), 7.55–7.53 (²H, m), 7.45–7.43 (²H, m), 6.56 (¹H, dd), 2.34 (³H, s). Compound 93 of this invention: 1 ¹H-NMR (CDCl₃) δ: 7.88 (¹H, d), 7.56–7.55 (²H, m), 7.39–7.37 (²H, m), 6.39 (¹H, d), 4.43 (²H, q), 2.27 (³H, s), 1.40 (³H, t). Compound 94 of this invention: 1 H-NMR (CDCl3) δ: 7.92 (1H, d), 7.53-7.52 (2H, m), 7.45-7.43 (2H, m), 6.47 (1H, d), 2.36 (3H, s).

[0146] This compound 95: 1 ¹H-NMR (CDCl₃) δ: 7.93 (¹H, br s), 7.64 (¹H, br s), 7.56–7.54 (²H, m), 7.39–7.37 (²H, m), 4.43 (²H, q), 2.22 (³H, s), 1.40 (³H, t). Compound 96 of this invention: 1¹H-NMR (CDCl₃) δ: 7.99 (¹H, br s), 7.73 (¹H, br s), 7.59–7.57 (²H, m), 7.43–7.41 (²H, m), 2.37 (³H, s). Compound 100 of this invention: 1 H-NMR (CDCl3) δ: 8.15 (1H, s), 7.69 (1H, s), 7.56-7.54 (2H, m), 7.44-7.41 (2H, m), 3.98 (3H, s), 2.46 (3H, s).

[0147] This compound 101: 1 ¹H-NMR (CDCl₃) δ: 8.51 (¹H, s), 7.84 (¹H, s), 7.56–7.52 (²H, m), 7.38–7.35 (²H, m), 7.15 (¹H, dd), 4.44 (²H, q), 2.34 (³H, s), 1.39 (³H, t). Compound 102 of this invention: 1 ¹H-NMR (CDCl₃) δ: 7.56–7.51 (2H, m), 7.49–7.46 (1H, m), 7.41–7.38 (1H, m), 7.38–7.34 (2H, m), 7.18–7.13 (1H, m), 4.41 (2H, q), 2.18 (3H, s), 1.37 (3H, t). Compound 103 of this invention: 1 H-NMR (CDCl3) δ: 7.58-7.54 (1H, m), 7.54-7.50 (2H, m), 7.50-7.46 (1H, m), 7.45-7.39 (2H, m), 7.22-7.18 (1H, m), 2.30 (3H, s).

[0148] This compound 104: 1 ¹H-NMR (CDCl₃) δ: 7.66–7.54 (2H, m), 7.48–7.38 (2H, m), 7.37–7.28 (1H, m), 6.91–6.84 (1H, m), 6.82–6.65 (2H, m), 2.37 (3H, s). Compound 105 of this invention: 1¹H-NMR (CDCl₃) δ: 7.59–7.49 (2H, m), 7.44–7.33 (2H, m), 7.28–7.19 (1H, m), 6.83–6.59 (3H, m), 4.39 (2H, q), 2.23 (3H, s), 1.37 (3H, t). Compound 106 of this invention: 1 H-NMR (CDCl3) δ: 7.57-7.47 (2H, m), 7.43-7.35 (2H, m), 7.01-6.92 (2H, m), 6.92-6.84 (2H, m), 4.38 (2H, q), 2.25 (3H, s), 1.38 (3H, t).

[0149] This compound 107: 1 ¹H-NMR (CDCl₃) δ: 7.56–7.47 (2H, m), 7.47–7.38 (2H, m), 7.08–6.88 (4H, m), 2.41 (3H, s). Compound 108 of this invention: 1 ¹H-NMR (CDCl₃) δ: 7.56–7.51 (2H, m), 7.48–7.41 (2H, m), 7.36–7.28 (1H, m), 6.91–6.83 (1H, m), 6.79–6.69 (2H, m), 2.38 (3H, s). Compound 109 of this invention: 1 H-NMR (CDCl3) δ: 7.59-7.48 (2H, m), 7.44-7.36 (2H, m), 7.27-7.15 (1H, m), 6.83-6.75 (1H, m), 6.75-6.69 (1H, m), 6.69-6.61 (1H, m), 4.38 (2H, q), 2.22 (3H, s), 1.36 (3H, t).

[0150] This compound 110: 1¹H-NMR (CDCl₃) δ: 7.58–7.47 (2H, m), 7.45–7.34 (2H, m), 7.11–6.97 (1H, m), 6.82–6.72 (1H, m), 6.68–6.58 (1H, m), 4.39 (2H, q), 2.24 (3H, s), 1.35 (3H, t). Compound 111 of this invention: 1 ¹H-NMR (CDCl₃) δ: 7.63–7.50 (2H, m), 7.50–7.37 (2H, m), 7.20–7.04 (1H, m), 6.95–6.84 (1H, m), 6.79–6.62 (1H, m), 2.42 (3H, s). Compound 112 of this invention: 1 H-NMR (DMSO-d6) δ: 8.01-7.94 (1H, m), 7.85-7.78 (1H, m), 7.65-7.59 (1H, m), 7.37-7.28 (1H, m), 7.13-7.05 (1H, m), 6.87-6.80 (1H, m), 2.08 (3H, s).

[0151] This compound 113: 1 ¹H-NMR (CDCl₃) δ: 7.65–7.52 (2H, m), 7.44–7.34 (2H, m), 7.18–7.06 (1H, m), 6.98–6.80 (2H, m), 2.46 (3H, s). Compound 114 of this invention: 1 ¹H-NMR (CDCl₃) δ: 7.58–7.51 (2H, m), 7.40–7.33 (2H, m), 7.07–6.98 (1H, m), 6.89–6.82 (1H, m), 6.80–6.73 (1H, m), 4.39 (2H, q), 2.31 (3H, s), 1.34 (3H, t). Compound 115 of this invention: 1 H-NMR (CDCl3) δ: 7.53-7.49 (2H, m), 7.48-7.44 (2H, m), 7.16-7.11 (1H, m), 6.95-6.90 (1H, m), 6.90-6.85 (1H, m), 2.49 (3H, s).

[0152] This compound 116: 1 ¹H-NMR (CDCl₃) δ: 7.50–7.46 (2H, m), 7.44–7.39 (2H, m), 7.09–7.02 (1H, m), 6.90–6.84 (1H, m), 6.82–6.75 (1H, m), 4.39 (2H, q), 2.32 (3H, s), 1.35 (3H, t). Compound 117 of this invention: 1 ¹H-NMR (CDCl₃) δ: 8.89–8.86 (¹H, m), 8.80–8.77 (¹H, m), 7.89–7.85 (¹H, m), 7.63–7.58 (¹H, m), 7.36–7.29 (¹H, m), 6.92–6.86 (¹H, m), 6.78–6.70 (²H, m), 2.41 (³H, s). Compound 118 of this invention: 1 H-NMR (CDCl3) δ: 8.82-8.79 (1H, m), 8.78-8.74 (1H, m), 7.85-7.82 (1H, m), 7.57-7.53 (1H, m), 7.27-7.22 (1H, m), 6.80-6.76 (1H, m), 6.76-6.72 (1H, m), 6.71-6.66 (1H, m), 4.40 (2H, q), 2.27 (3H, s), 1.38 (3H, t).

[0153] This compound 119: 1 ¹H-NMR (CDCl₃) δ: 8.47–8.42 (¹H, m), 7.69–7.63 (¹H, m), 7.56–7.51 (²H, m), 7.46–7.42 (¹H, m), 7.36–7.31 (²H, m), 7.20–7.14 (¹H, m), 4.24 (²H, s), 2.50 (³H, s). Compound 120 of this invention: 1¹H-NMR (CDCl₃) δ: 7.71 (¹H, s), 7.63 (¹H, s), 7.05–6.97 (¹H, m), 6.90–6.82 (¹H, m), 6.80–6.72 (¹H, m), 4.39 (2H, q), 3.99 (3H, s), 2.40 (3H, s), 1.35 (3H, t). Compound 121 of this invention: 1 H-NMR (CDCl3) δ: 8.31-8.28 (1H, m), 7.57-7.52 (2H, m), 7.51-7.46 (1H, m), 7.41-7.37 (1H, m), 7.36-7.31 (2H, m), 4.20 (2H, s), 2.50 (3H, s).

[0154] This compound 122: 1 ¹H-NMR (CDCl₃) δ: 8.25–8.21 (¹H, m), 7.43–7.40 (¹H, m), 7.40–7.35 (¹H, m), 7.33–7.25 (¹H, m), 6.40–6.36 (¹H, m), 4.14 (²H, s), 3.89 (³H, s), 2.51 (³H, s). Compound 123 of this invention: 1 ¹H-NMR (CDCl₃) δ: 7.51 (¹H, d), 7.18–7.08 (¹H, m), 6.86–6.83 (¹H, m), 6.69–6.65 (¹H, m), 6.54 (¹H, d), 3.98 (³H, s), 2.51 (³H, s). Compound 124 of this invention: 1 H-NMR (CDCl3) δ: 7.51 (1H, d), 7.05-7.03 (1H, m), 6.95-6.90 (1H, m), 6.87-6.81 (1H, m), 6.53 (1H, d), 3.97 (3H, s), 2.58 (3H, s).

[0155] This compound 125: 1¹H-NMR (CDCl₃) δ: 7.48 (¹H, d), 7.11–7.01 (¹H, m), 6.84–6.77 (¹H, m), 6.69–6.63 (¹H, m), 6.44 (¹H, d), 4.39 (2H, q), 3.96 (3H, s), 2.35 (3H, s), 1.36 (3H, t). Compound 126 of this invention: 1 ¹H-NMR (CDCl₃) δ: 8.26 (¹H, d), 7.47–7.45 (¹H, m), 7.45–7.43 (¹H, m), 7.30–7.25 (¹H, m), 6.34 (¹H, d), 4.39 (2H, q), 4.11 (2H, s), 3.91 (3H, s), 2.39 (3H, s), 1.36 (3H, t). Compound 127 of this invention: 1 H-NMR (CDCl3) δ: 7.80 (1H, br s), 7.67 (1H, br s), 7.13-7.06 (1H, m), 6.93-6.91 (1H, m), 6.87-6.84 (1H, m), 4.01 (3H, s), 2.58 (3H, s).

[0156] This compound 128: 1 ¹H-NMR (CDCl₃) δ: 7.48 (¹H, d), 7.36–7.28 (¹H, m), 6.87–6.75 (²H, m), 6.44 (¹H, d), 4.04 (²H, s), 3.95 (³H, s), 2.42 (³H, s). Compound 129 of this invention: 1 ¹H-NMR (CDCl₃) δ: 7.61–7.55 (2H, m), 7.43–7.38 (2H, m), 6.66–6.59 (1H, m), 6.56–6.48 (2H, m), 2.37 (3H, s). Compound 130 of this invention: 1H-NMR (CDCl3) δ: 7.44 (1H, d), 7.41-7.32 (1H, m), 6.82-6.71 (2H, m), 6.35 (1H, d), 4.41 (2H, q), 3.94 (2H, s), 3.93 (3H, s), 2.25 (3H, s), 1.37 (3H, t).

[0157] This compound 131: 1 ¹H-NMR (CDCl₃) δ: 7.57–7.52 (2H, m), 7.41–7.36 (2H, m), 6.57–6.51 (1H, m), 6.51–6.46 (2H, m), 4.42 (2H, q), 2.24 (3H, s), 1.36 (3H, t). Compound 132 of this invention: 1 ¹H-NMR (CDCl₃) δ: 8.40 (¹H, d), 8.27 (¹H, d), 7.62–7.58 (²H, m), 7.44–7.39 (²H, m), 7.30 (¹H, dd), 2.42 (³H, s). Compound 133 of this invention: 1 H-NMR (CDCl3) δ: 8.38 (1H, d), 8.28 (1H, d), 7.53 (1H, d), 7.28-7.27 (1H, m), 6.56 (1H, d), 4.00 (3H, s), 2.55 (3H, s).

[0158] This compound 134: 1 ¹H-NMR (CDCl₃) δ: 8.29 (¹H, d), 8.25 (¹H, d), 7.59–7.54 (²H, m), 7.43–7.37 (²H, m), 7.25 (¹H, dd), 4.40 (²H, q), 2.29 (³H, s), 1.37 (³H, t). Compound 135 of this invention: 1¹H-NMR (CDCl₃) δ: 8.32–8.25 (2H, m), 7.48 (1H, d), 7.23 (1H, dd), 6.46 (1H, d), 4.40 (2H, q), 3.98 (3H, s), 2.38 (3H, s), 1.36 (3H, t). Compound 136 of this invention: 1 H-NMR (CDCl3) δ: 7.71 (1H, br s), 7.59 (1H, br s), 7.40-7.31 (1H, m), 6.87-6.77 (2H, m), 4.03 (2H, s), 3.97 (3H, s), 2.47 (3H, s).

[0159] This compound 137: 1 ¹H-NMR (CDCl₃) δ: 8.31–8.28 (¹H, m), 7.73 (¹H, br s), 7.61 (¹H, br s), 7.50–7.44 (¹H, m), 7.41–7.33 (¹H, m), 4.20 (2H, s), 3.98 (3H, s), 2.63 (3H, s). Compound 138 of this invention: 1 ¹H-NMR (CDCl₃) δ: 7.62–7.56 (2H, m), 7.43–7.36 (2H, m), 7.17–7.07 (1H, m), 6.89–6.80 (2H, m), 2.45 (3H, s). Compound 139 of this invention: 1 H-NMR (CDCl3) δ: 8.39 (1H, d, 8.27 (1H, d), 7.83 (1H, s), 7.69 (1H, s), 7.30-7.28 (1H, m), 4.01 (3H, s), 2.54 (3H, s).

[0160] This compound 140: 1 ¹H-NMR (CDCl₃) δ: 7.59–7.49 (2H, m), 7.43–7.33 (2H, m), 7.11–6.99 (1H, m), 6.78–6.65 (2H, m), 4.40 (2H, q), 2.29 (3H, s), 1.34 (3H, t). Compound 141 of this invention: 1¹H-NMR (CDCl₃) δ: 7.61 (¹H, s), 7.56 (¹H, s), 7.45–7.36 (¹H, m), 6.82–6.72 (²H, m), 4.42 (²H, q), 3.96 (³H, s), 3.94 (²H, s), 2.28 (³H, s), 1.38 (³H, t). Compound 142 of this invention: 1 H-NMR (CDCl3) δ: 8.26 (1H, d), 7.61 (1H, s), 7.56 (1H, s), 7.49 (1H, dd), 7.33-7.27 (1H, m), 4.40 (2H, q), 4.11 (2H, s), 3.96 (3H, s), 2.42 (3H, s), 1.36 (3H, t).

[0161] This compound 143: 1 ¹H-NMR (CDCl₃) δ: 8.27 (¹H, d), 8.23 ​​(¹H, d), 7.74 (¹H, br s), 7.64 (¹H, br s), 7.21 (¹H, dd), 4.37 (2H, q), 3.97 (3H, s), 2.30 (3H, s), 1.34 (3H, t). Compound 144 of this invention: 1 ¹H-NMR (CDCl₃) δ: 7.48–7.42 (2H, m), 7.33–7.27 (2H, m), 7.19–7.10 (1H, m), 6.88–6.81 (1H, m), 6.72–6.65 (1H, m), 2.38 (3H, s). Compound 145 of this invention: 1 H-NMR (CDCl3) δ: 7.82 (1H, br s), 7.68 (1H, br s), 7.19-7.10 (1H, m), 6.87-6.80 (1H, m), 6.71-6.64 (1H, m), 4.01 (3H, s), 2.52 (3H, s).

[0162] This compound 146: 1¹H-NMR (CDCl₃) δ: 7.46–7.38 (2H, m), 7.31–7.23 (2H, m), 7.14–7.04 (1H, m), 6.86–6.77 (1H, m), 6.72–6.64 (1H, m), 4.41 (2H, q), 2.24 (3H, s), 1.37 (3H, t). Compound 147 of this invention: 1 ¹H-NMR (CDCl₃) δ: 7.72 (¹H, br s), 7.64 (¹H, br s), 7.10–7.02 (¹H, m), 6.82–6.75 (¹H, m), 6.68–6.62 (¹H, m), 4.40 (2H, q), 3.99 (3H, s), 2.32 (3H, s), 1.37 (3H, t). Compound 148 of this invention: 1 H-NMR (CDCl3) δ: 7.63-7.48 (3H, m), 7.38-7.33 (1H, m), 7.19-7.10 (1H, m), 6.89-6.82 (1H, m), 6.72-6.66 (1H, m), 2.40 (3H, s).

[0163] This compound 149: 1 ¹H-NMR (CDCl₃) δ: 7.57–7.52 (2H, m), 7.40–7.35 (2H, m), 7.12–7.03 (1H, m), 6.83–6.77 (1H, m), 6.70–6.63 (1H, m), 5.31–5.22 (1H, m), 2.23 (3H, s), 1.35 (6H, d). Compound 150 of this invention: 1 ¹H-NMR (CDCl₃) δ: 7.62–7.54 (2H, m), 7.43–7.36 (2H, m), 7.14–7.04 (1H, m), 6.84–6.77 (1H, m), 6.71–6.63 (1H, m), 4.94 (2H, s), 2.27 (3H, s). Compound 151 of this invention: 1H-NMR (CDCl3) δ: 7.58-7.52 (2H, m), 7.41-7.35 (2H, m), 7.12-7.03 (1H, m), 6.84-6.76 (1H, m), 6.70-6.64 (1H, m), 3.93 (3H, s), 2.25 (3H, s).

[0164] This compound 152: 1 ¹H-NMR (CDCl₃) δ: 7.57-7.52 (2H, m), 7.42-7.36 (2H, m), 7.11-7.02 (1H, m), 6.83-6.74 (1H, m), 6.70-6.62 (1H, m), 4.31 (2H, t), 2.24 (3H, s), 1.75 (2H, td), 0.98 (3H, t). Compound 153 of this invention: 1 ¹H-NMR (CDCl₃) δ: 7.58–7.45 (3H, m), 7.35–7.29 (1H, m), 7.13–7.04 (1H, m), 6.85–6.78 (1H, m), 6.71–6.64 (1H, m), 4.41 (2H, q), 2.26 (3H, s), 1.37 (3H, t). Compound 154 of this invention: 1 H-NMR (CDCl3) δ: 8.62 (1H, d), 7.71 (1H, dd), 7.42 (1H, d), 7.15 (1H, dd), 6.89-6.82 (1H, m), 6.73-6.66 (1H, m), 2.71 (3H, s), 2.41 (3H, s).

[0165] This compound 155: 1 ¹H-NMR (CDCl₃) δ: 7.41–7.36 (2H, m), 7.33–7.28 (2H, m), 7.18–7.09 (1H, m), 6.88–6.81 (1H, m), 6.72–6.65 (1H, m), 2.47 (3H, s), 2.38 (3H, s). Compound 156 of this invention: 1¹H-NMR (CDCl₃) δ: 7.57–7.48 (2H, m), 7.44–7.37 (2H, m), 7.11–6.99 (1H, m), 6.83–6.74 (1H, m), 6.69–6.61 (1H, m), 4.83 (2H, s), 4.20 (2H, q), 2.23 (3H, s), 1.25 (3H, t). Compound 157 of this invention: 1 H-NMR (CDCl3) δ: 7.56-7.51 (2H, m), 7.40-7.35 (2H, m), 7.11-7.02 (1H, m), 6.82-6.75 (1H, m), 6.68-6.62 (1H, m), 4.51-4.44 (2H, m), 3.72-3.63 (2H, m), 3.36 (3H, s), 2.23 (3H, s).

[0166] This compound 158: 1 ¹H-NMR (CDCl₃) δ: 7.62–7.56 (2H, m), 7.42–7.37 (2H, m), 7.09–6.95 (2H, m), 6.88–6.81 (1H, m), 2.45 (3H, s). Compound 159 of this invention: 1 ¹H-NMR (CDCl₃) δ: 7.87–7.80 (2H, m), 7.71–7.64 (2H, m), 7.15–7.04 (1H, m), 6.94–6.85 (1H, m), 6.79–6.70 (1H, m), 2.37 (3H, s). Compound 160 of this invention: 1 H-NMR (CDCl3) δ: 7.42-7.37 (2H, m), 7.35-7.30 (2H, m), 7.18-7.10 (1H, m), 6.88-6.81 (1H, m), 6.72-6.65 (1H, m), 2.55 (3H, s), 2.37 (3H, s).

[0167] This compound 161: 1¹H-NMR (CDCl₃) δ: 8.59 (¹H, d), 7.69 (¹H, dd), 7.35 (¹H, d), 7.10–6.99 (¹H, m), 6.82–6.74 (¹H, m), 6.68–6.61 (¹H, m), 4.38 (2H, q), 2.67 (3H, s), 2.24 (3H, s), 1.34 (3H, t). Compound 162 of this invention: 1 ¹H-NMR (CDCl₃) δ: 7.38–7.33 (2H, m), 7.30–7.26 (2H, m), 7.12–7.03 (1H, m), 6.84–6.77 (1H, m), 6.71–6.64 (1H, m), 4.39 (2H, q), 2.45 (3H, s), 2.22 (3H, s), 1.36 (3H, t). Compound 163 of this invention: 1 H-NMR (CDCl3) δ: 7.58-7.51 (2H, m), 7.48-7.40 (2H, m), 6.67-6.56 (2H, m), 2.30 (3H, s).

[0168] This compound 164: 1 ¹H-NMR (CDCl₃) δ: 7.94–7.88 (2H, m), 7.69–7.63 (2H, m), 7.20–7.10 (1H, m), 6.91–6.83 (1H, m), 6.75–6.68 (1H, m), 2.81 (3H, s), 2.42 (3H, s). Compound 165 of this invention: 1 ¹H-NMR (CDCl₃) δ: 8.26–8.19 (2H, m), 7.76–7.67 (2H, m), 7.21–7.11 (1H, m), 6.90–6.82 (1H, m), 6.74–6.66 (1H, m), 3.14 (3H, s), 2.43 (3H, s). Compound 166 of this invention: 1H-NMR (CDCl3) δ: 7.58-7.51 (2H, m), 7.40-7.34 (2H, m), 7.00-6.84 (2H, m), 6.80-6.73 (1H, m), 4.39 (2H, q), 2.30 (3H, s), 1.35 (3H, t).

[0169] This compound 167: 1 ¹H-NMR (CDCl₃) δ: 7.58–7.52 (2H, m), 7.42–7.35 (2H, m), 6.64–6.55 (2H, m), 4.40 (2H, q), 2.23 (3H, s), 1.36 (3H, t). Compound 168 of this invention: 1 ¹H-NMR (CDCl₃) δ: 7.62–7.56 (2H, m), 7.44–7.38 (2H, m), 7.38–7.33 (1H, m), 6.85–6.79 (1H, m), 6.75–6.69 (1H, m), 2.39 (3H, s). Compound 169 of this invention: 1 H-NMR (CDCl3) δ: 7.48-7.42 (2H, m), 7.40-7.34 (1H, m), 7.33-7.28 (2H, m), 6.84-6.79 (1H, m), 6.74-6.69 (1H, m), 2.38 (3H, s).

[0170] This compound 170: 1 ¹H-NMR (CDCl₃) δ: 8.36–8.30 (¹H, m), 8.24–8.19 (¹H, m), 7.65–7.56 (²H, m), 7.45–7.37 (²H, m), 7.11–7.04 (¹H, m), 2.42 (³H, s). Compound 171 of this invention: 1 ¹H-NMR (CDCl₃) δ: 7.47–7.40 (2H, m), 7.31–7.20 (3H, m), 6.79–6.73 (1H, m), 6.73–6.66 (1H, m), 4.40 (2H, q), 2.21 (3H, s), 1.35 (3H, t). Compound 172 of this invention: 1H-NMR (CDCl3) δ: 7.59-7.53 (2H, m), 7.44-7.37 (2H, m), 7.15-7.09 (1H, m), 7.06-7.00 (1H, m), 6.89-6.83 (1H, m), 2.38 (3H, s).

[0171] This compound 173: 1 ¹H-NMR (CDCl₃) δ: 7.80–7.77 (¹H, m), 7.57–7.53 (²H, m), 7.36–7.31 (²H, m), 6.54–6.51 (¹H, m), 5.41 (²H, s), 2.63 (³H, s). Compound 174 of this invention: 1 ¹H-NMR (CDCl₃) δ: 7.69–7.62 (¹H, m), 7.56–7.45 (²H, m), 7.39–7.30 (²H, m), 6.20–6.12 (¹H, m), 5.28 (²H, br s), 2.60 (³H, s). Compound 175 of this invention: 1 H-NMR (CDCl3) δ: 7.60-7.55 (2H, m), 7.45-7.40 (2H, m), 6.91-6.80 (3H, m), 2.78 (2H, q), 1.16 (3H, t).

[0172] This compound 176: 1 ¹H-NMR (CDCl₃) δ: 7.60–7.50 (2H, m), 7.48–7.39 (2H, m), 6.67–6.58 (1H, m), 6.58–6.50 (2H, m), 2.72 (2H, q), 1.12 (3H, t). Compound 177 of this invention: 1 ¹H-NMR (CDCl₃) δ: 7.61–7.55 (2H, m), 7.46–7.41 (2H, m), 7.35–7.27 (1H, m), 6.90–6.83 (1H, m), 6.77–6.69 (2H, m), 2.74 (2H, q), 1.12 (3H, t). Compound 178 of this invention: 1H-NMR (CDCl3) δ: 7.56-7.47 (2H, m), 7.45-7.36 (2H, m), 7.21-7.08 (1H, m), 6.94-6.85 (1H, m), 6.77-6.67 (1H, m), 2.89-2.86 (1H, m), 1.33 (6H, d).

[0173] This compound 179: 1 ¹H-NMR (CDCl₃) δ: 8.51 (¹H, d), 7.63 (¹H, dd), 7.38 (¹H, d), 7.19–7.09 (¹H, m), 6.90–6.82 (¹H, m), 6.73–6.65 (¹H, m), 2.19–2.11 (¹H, m), 2.16 (³H, s), 1.17–1.09 (⁴H, m). Compound 180 of this invention: 1 ¹H-NMR (CDCl₃) δ: 8.64 (¹H, d), 7.73 (¹H, dd), 7.45–7.39 (¹H, m), 7.19–7.10 (¹H, m), 6.90–6.82 (¹H, m), 6.73–6.66 (¹H, m), 2.96 (2H, q), 2.41 (3H, s), 1.38 (3H, t). Compound 181 of this invention: 1 H-NMR (CDCl3) δ: 7.61-7.56 (2H, m), 7.42-7.36 (2H, m), 7.17-7.08 (1H, m), 7.03-6.94 (2H, m), 2.51 (3H, s).

[0174] This compound 182: 1 ¹H-NMR (CDCl₃) δ: 7.53–7.48 (2H, m), 7.44 (1H, d), 7.39–7.33 (2H, m), 6.23 (1H, d), 5.34 (2H, s), 2.42 (3H, s). Compound 183 of this invention: 1¹H-NMR (CDCl₃) δ: 7.37–7.32 (2H, m), 7.09–7.04 (2H, m), 6.66–6.58 (1H, m), 6.56–6.47 (2H, m), 3.90 (3H, s), 2.36 (3H, s). Compound 184 of this invention: 1 H-NMR (CDCl3) δ: 8.66 (1H, d), 7.85-7.76 (1H, m), 7.37-7.32 (1H, m), 7.16-7.08 (1H, m), 6.95-6.87 (1H, m), 6.78-6.71 (1H, m), 2.74 (2H, q), 2.69 (3H, s), 1.13 (3H, t).

[0175] This compound 185: 1 ¹H-NMR (CDCl₃) δ: 8.54 (¹H, d), 7.70 (¹H, dd), 7.31 (¹H, d), 7.12 (¹H, dd), 6.93–6.86 (¹H, m), 6.75–6.70 (¹H, m), 2.73 (2H, q), 2.21–2.09 (¹H, m), 1.19–1.07 (7H, m). Compound 186 of this invention: 1 ¹H-NMR (CDCl₃) δ: 7.58–7.51 (2H, m), 7.40–7.34 (2H, m), 7.05–6.97 (1H, m), 6.94–6.86 (2H, m), 4.36 (2H, q), 2.38 (3H, s), 1.33 (3H, t). Compound 187 of this invention: 1 H-NMR (CDCl3) δ: 8.50 (1H, d), 7.61 (1H, dd), 7.34 (1H, d), 7.12-7.02 (1H, m), 6.85-6.76 (1H, m), 6.70-6.62 (1H, m), 4.40 (2H, q), 2.25 (3H, s), 2.18-2.09 (1H, m), 1.35 (3H, t), 1.15-1.08 (4H, m).

[0176] This compound 188: 1¹H-NMR (CDCl₃) δ: 8.63 (¹H, d), 7.70 (¹H, dd), 7.39 (¹H, d), 7.13–7.03 (¹H, m), 6.85–6.77 (¹H, m), 6.71–6.64 (¹H, m), 4.40 (2H, q), 2.95 (2H, q), 2.26 (3H, s), 1.43–1.31 (6H, m). Compound 189 of this invention: 1 ¹H-NMR (CDCl₃) δ: 7.61–7.57 (2H, m), 7.39–7.35 (2H, m), 6.67–6.60 (1H, m), 6.54–6.47 (2H, m), 2.96–2.86 (1H, m), 1.34 (6H, d). Compound 190 of this invention: 1 H-NMR (CDCl3) δ: 8.57-8.47 (1H, m), 7.99-7.93 (1H, m), 7.84-7.74 (1H, m), 7.58-7.50 (1H, m), 7.41-7.33 (1H, m), 3.36 (3H, s), 3.04 (3H, s), 2.95 (3H, s).

[0177] This compound 191: 1 ¹H-NMR (CDCl₃) δ: 8.44–8.37 (2H, m), 8.03–7.96 (2H, m), 7.85–7.76 (1H, m), 7.54–7.46 (1H, m), 7.38–7.31 (1H, m), 3.05 (3H, s). Compound 192 of this invention: 1 ¹H-NMR (CDCl₃) δ: 7.48–7.43 (¹H, m), 7.43–7.35 (¹H, m), 7.30–7.25 (¹H, m), 7.18–7.10 (¹H, m), 6.92–6.84 (¹H, m), 6.75–6.68 (¹H, m), 2.41 (³H, s). Compound 193 of this invention: 1H-NMR (CDCl3) δ: 8.28-8.21 (2H, m), 8.06-8.01 (2H, m), 8.01-7.95 (1H, m), 7.57-7.50 (1H, m), 7.42-7.34 (2H, m), 3.62-3.52 (1H, m), 2.00 (6H, d).

[0178] This compound 194: 1 ¹H-NMR (CDCl₃) δ: 7.73–7.67 (2H, m), 7.34–7.29 (2H, m), 7.11–7.02 (1H, m), 6.83–6.75 (1H, m), 6.69–6.63 (1H, m), 4.40 (2H, q), 2.24 (3H, s), 1.36 (3H, t). Compound 195 of this invention: 1 ¹H-NMR (CDCl₃) δ: 7.43–7.31 (2H, m), 7.26–7.20 (1H, m), 7.12–7.02 (1H, m), 6.83–6.75 (1H, m), 6.70–6.63 (1H, m), 4.41 (2H, q), 2.25 (3H, s), 1.36 (3H, t). Compound 196 of this invention: 1 H-NMR (CDCl3) δ: 7.59-7.53 (2H, m), 7.44-7.37 (2H, m), 6.57-6.52 (1H, m), 6.52-6.47 (2H, m), 4.41 (2H, q), 2.61 (2H, q), 1.37 (3H, t), 1.06 (3H, t).

[0179] This compound 197: 1 ¹H-NMR (CDCl₃) δ: 7.60–7.52 (2H, m), 7.44–7.36 (2H, m), 7.13–7.03 (1H, m), 6.85–6.77 (1H, m), 6.71–6.64 (1H, m), 4.40 (2H, q), 2.62 (2H, q), 1.36 (3H, t), 1.05 (3H, t). Compound of this invention 198: 1¹H-NMR (CDCl₃) δ: 7.58–7.53 (2H, m), 7.42–7.36 (2H, m), 7.13–7.04 (1H, m), 6.84–6.77 (1H, m), 6.70–6.64 (1H, m), 5.30–5.22 (1H, m), 2.61 (2H, q), 1.35 (6H, d), 1.05 (3H, t). Compound of this invention 199: 1 H-NMR (CDCl3) δ: 7.58-7.52 (2H, m), 7.44-7.39 (2H, m), 7.27-7.21 (1H, m), 6.81-6.65 (3H, m), 4.40 (2H, q), 2.61 (2H, q), 1.36 (3H, t), 1.04 (3H, t).

[0180] This compound 200: 1 ¹H-NMR (CDCl₃) δ: 8.54–8.51 (¹H, m), 7.62 (¹H, dd), 7.35 (¹H, dd), 7.12–7.04 (¹H, m), 6.85–6.78 (¹H, m), 6.70–6.64 (¹H, m), 4.40 (2H, q), 2.62 (2H, q), 2.19–2.11 (¹H, m), 1.36 (3H, t), 1.15–1.10 (4H, m), 1.06 (3H, t). Compound 201 of this invention: 1 ¹H-NMR (CDCl₃) δ: 8.51-8.48 (¹H, m), 7.65-7.58 (¹H, m), 7.37-7.30 (¹H, m), 7.11-7.01 (¹H, m), 6.84-6.74 (¹H, m), 6.70-6.62 (¹H, m), 3.91 (³H, s), 2.24 (³H, s), 2.18-2.09 (¹H, m), 1.16-1.07 (⁴H, m). Compound 202 of this invention: 1H-NMR (CDCl3) δ: 8.53 (1H, d), 7.62 (1H, dd), 7.37-7.34 (1H, m), 7.12-7.04 (1H, m), 6.86-6.79 (1H, m), 6.71-6.65 (1H, m), 3.92 (3H, s), 2.67-2.59 (2H, m), 2.19-2.11 (1H, m), 1.16-1.11 (4H, m), 1.07 (3H, t).

[0181] This compound 203: 1 ¹H-NMR (CDCl₃) δ: 7.58–7.53 (2H, m), 7.38–7.34 (2H, m), 7.29–7.22 (1H, m), 6.81–6.71 (2H, m), 6.71–6.65 (1H, m), 4.39 (2H, q), 2.80–2.71 (1H, m), 1.35 (3H, t), 1.28 (6H, d). Compound 204 of this invention: 1 ¹H-NMR (CDCl₃) δ: 7.58–7.52 (2H, m), 7.38–7.33 (2H, m), 6.56–6.45 (3H, m), 4.39 (2H, q), 2.81–2.70 (1H, m), 1.35 (3H, t), 1.28 (6H, d). Compound 205 of this invention: 1 H-NMR (CDCl3) δ: 7.62-7.56 (2H, m), 7.43-7.38 (2H, m), 7.35-7.30 (2H, m), 6.95-6.87 (2H, m), 2.39 (3H, s).

[0182] This compound 206: 1 ¹H-NMR (CDCl₃) δ: 7.60–7.53 (2H, m), 7.43–7.38 (2H, m), 7.19–7.11 (1H, m), 6.89–6.83 (1H, m), 6.72–6.66 (1H, m), 2.71–2.64 (2H, m), 1.56–1.47 (2H, m), 0.84 (3H, t). Compound 207 of this invention: 1¹H-NMR (CDCl₃) δ: 7.57–7.51 (2H, m), 7.38–7.32 (2H, m), 7.13–7.03 (1H, m), 6.83–6.75 (1H, m), 6.69–6.62 (1H, m), 4.38 (2H, q), 2.83–2.69 (1H, m), 1.34 (3H, t), 1.28 (6H, d). Compound 208 of this invention: 1 H-NMR (CDCl3) δ: 8.53-8.51 (1H, m), 7.66-7.61 (1H, m), 7.41-7.37 (1H, m), 7.36-7.28 (1H, m), 6.91-6.84 (1H, m), 6.77-6.69 (2H, m), 2.39 (3H, s), 2.19-2.12 (1H, m), 1.16-1.12 (4H, m).

[0183] This compound 209: 1 ¹H-NMR (CDCl₃) δ: 8.52–8.49 (¹H, m), 7.63–7.58 (¹H, m), 7.36–7.32 (¹H, m), 7.28–7.21 (¹H, m), 6.80–6.71 (²H, m), 6.71–6.65 (¹H, m), 4.40 (²H, q), 2.24 (³H, s), 2.17–2.10 (¹H, m), 1.36 (³H, t), 1.11 (⁴H, q). Compound 210 of this invention: 1 ¹H-NMR (CDCl₃) δ: 8.61-8.59 (¹H, m), 7.75-7.69 (¹H, m), 7.39-7.34 (¹H, m), 7.34-7.28 (¹H, m), 6.91-6.83 (¹H, m), 6.79-6.71 (²H, m), 2.75 (²H, q), 2.22-2.15 (¹H, m), 1.24-1.08 (⁷H, m). Compound 211 of this invention: 1H-NMR (CDCl3) δ: 8.58-8.54 (1H, m), 7.70-7.64 (1H, m), 7.38-7.33 (1H, m), 7.28-7.21 (1H, m), 6.81-6.66 (3H, m), 4.40 (2H, q), 2.62 (2H, q), 2.22-2.14 (1H, m), 1.36 (3H, t), 1.19-1.12 (4H, m), 1.06 (3H, t).

[0184] This compound 212: 1 ¹H-NMR (CDCl₃) δ: 8.53–8.48 (¹H, m), 7.63–7.57 (¹H, m), 7.37–7.32 (¹H, m), 7.28–7.22 (¹H, m), 6.82–6.64 (³H, m), 4.38 (²H, q), 2.81–2.71 (¹H, m), 2.22–2.12 (¹H, m), 1.35 (³H, t), 1.29 (⁶H, d), 1.16–1.11 (⁴H, m). Compound 213 of this invention: 1 ¹H-NMR (CDCl₃) δ: 7.63–7.56 (2H, m), 7.44–7.36 (2H, m), 7.21–7.04 (4H, m), 2.45 (3H, s). Compound 214 of this invention: 1 H-NMR (CDCl3) δ: 7.58-7.51 (2H, m), 7.40-7.34 (2H, m), 7.15-7.07 (1H, m), 7.07-6.98 (3H, m), 4.39 (2H, q), 2.31 (3H, s), 1.36 (3H, t).

[0185] This compound 215: 1 ¹H-NMR (CDCl₃) δ: 7.62–7.57 (2H, m), 7.44–7.38 (2H, m), 7.32–7.27 (1H, m), 7.16–7.12 (1H, m), 6.98–6.94 (1H, m), 6.89–6.83 (1H, m), 2.39 (3H, s). Compound 216 of this invention: 1¹H-NMR (CDCl₃) δ: 7.58–7.51 (2H, m), 7.40–7.34 (2H, m), 7.25–7.20 (1H, m), 7.07–7.03 (1H, m), 6.95–6.92 (1H, m), 6.88–6.82 (1H, m), 4.41 (2H, q), 2.24 (3H, s), 1.36 (3H, t). Compound 217 of this invention: 1 H-NMR (CDCl3) δ: 7.55-7.50 (2H, m), 7.50-7.46 (2H, m), 7.18-7.09 (1H, m), 6.89-6.82 (1H, m), 6.71-6.65 (1H, m), 1.70-1.61 (1H, m), 1.03-0.93 (4H, m).

[0186] This compound 218: 1 ¹H-NMR (CDCl₃) δ: 7.61–7.56 (2H, m), 7.50–7.44 (1H, m), 7.43–7.36 (2H, m), 7.26–7.20 (1H, m), 7.16–7.09 (1H, m), 6.90–6.84 (1H, m), 2.44 (3H, s). Compound 219 of this invention: 1 ¹H-NMR (CDCl₃) δ: 7.57–7.51 (2H, m), 7.43–7.39 (1H, m), 7.39–7.34 (2H, m), 7.18–7.13 (1H, m), 7.05–6.98 (1H, m), 6.83–6.78 (1H, m), 4.40 (2H, q), 2.28 (3H, s), 1.36 (3H, t). Compound 220 of this invention: 1 H-NMR (CDCl3) δ: 7.36-7.17 (4H, m), 6.90-6.83 (1H, m), 6.80-6.69 (2H, m), 2.40 (3H, s).

[0187] This compound 221: 1¹H-NMR (CDCl₃) δ: 7.55-7.50 (2H, m), 7.46-7.40 (2H, m), 7.13-7.04 (1H, m), 6.81-6.74 (1H, m), 6.67-6.60 (1H, m), 4.39 (2H, q), 1.63-1.54 (1H, m), 1.37 (3H, t), 0.89-0.75 (4H, m). Compound 222 of this invention: 1 ¹H-NMR (CDCl₃) δ: 7.43–7.40 (¹H, m), 7.34–7.28 (¹H, m), 7.26–7.19 (²H, m), 6.90–6.82 (¹H, m), 6.81–6.73 (²H, m), 2.75 (²H, q), 1.15 (³H, t). Compound 223 of this invention: 1 H-NMR (CDCl3) δ: 7.58-7.53 (2H, m), 7.43-7.38 (2H, m), 7.12-7.03 (1H, m), 6.84-6.77 (1H, m), 6.70-6.64 (1H, m), 3.92 (3H, s), 2.63 (2H, q), 1.05 (3H, t).

[0188] This compound 224: 1 ¹H-NMR (CDCl₃) δ: 7.61–7.55 (2H, m), 7.45–7.39 (2H, m), 7.09–7.01 (2H, m), 6.97–6.90 (2H, m), 2.76 (2H, q), 1.14 (3H, t). Compound 225 of this invention: 1 ¹H-NMR (CDCl₃) δ: 7.58–7.52 (2H, m), 7.43–7.36 (2H, m), 7.03–6.94 (2H, m), 6.94–6.85 (2H, m), 4.39 (2H, q), 2.63 (2H, q), 1.36 (3H, t), 1.05 (3H, t). Compound 226 of this invention: 1H-NMR (CDCl3) δ: 7.61-7.56 (2H, m), 7.45-7.39 (2H, m), 7.32-7.27 (1H, m), 7.17-7.12 (1H, m), 7.00-6.95 (1H, m), 6.89-6.82 (1H, m), 2.74 (2H, q), 1.13 (3H, t).

[0189] This compound 227: 1 ¹H-NMR (CDCl₃) δ: 7.58-7.52 (2H, m), 7.43-7.37 (2H, m), 7.25-7.19 (1H, m), 7.07-7.02 (1H, m), 6.97-6.93 (1H, m), 6.87-6.81 (1H, m), 4.40 (2H, q), 2.60 (2H, q), 1.36 (3H, t), 1.04 (3H, t). Compound 228 of this invention: 1 ¹H-NMR (CDCl₃) δ: 7.30–7.21 (2H, m), 7.21–7.11 (2H, m), 6.89–6.82 (1H, m), 6.74–6.64 (1H, m), 2.41 (3H, s). Compound 229 of this invention: 1 H-NMR (CDCl3) δ: 7.30-7.20 (3H, m), 7.19-7.11 (1H, m), 6.90-6.83 (1H, m), 6.72-6.66 (1H, m), 2.77 (2H, q), 1.17 (3H, t).

[0190] This compound 230: 1 ¹H-NMR (CDCl₃) δ: 7.25–7.18 (3H, m), 7.13–7.04 (1H, m), 6.84–6.77 (1H, m), 6.70–6.64 (1H, m), 4.40 (2H, q), 2.64 (2H, q), 1.36 (3H, t), 1.09 (3H, t). Compound 231 of this invention: 1¹H-NMR (CDCl₃) δ: 7.24–7.15 (3H, m), 7.12–7.04 (1H, m), 6.84–6.77 (1H, m), 6.70–6.64 (1H, m), 4.40 (2H, q), 2.26 (3H, s), 1.36 (3H, t). Compound 232 of this invention: 1 H-NMR (CDCl3) δ: 7.60-7.55 (2H, m), 7.45-7.40 (2H, m), 7.35-7.29 (2H, m), 6.94-6.88 (2H, m), 2.75 (2H, q), 1.13 (3H, t).

[0191] This compound 233: 1 ¹H-NMR (CDCl₃) δ: 8.53 (¹H, d), 7.87 (¹H, d), 7.15 (¹H, q), 6.90–6.82 (¹H, m), 6.73–6.65 (¹H, m), 2.76 (³H, s), 2.43 (³H, s). Compound 234 of this invention: 1 ¹H-NMR (CDCl₃) δ: 7.94 (¹H, s), 7.15–7.05 (¹H, m), 6.87–6.77 (¹H, m), 6.72–6.61 (¹H, m), 3.90 (³H, s), 2.29 (³H, s). Compound 235 of this invention: 1 H-NMR (CDCl3) δ: 8.17 (1H, s), 7.18-7.10 (1H, m), 6.89-6.83 (1H, m), 6.70-6.62 (1H, m), 4.06 (3H, s), 2.80 (2H, q), 1.22 (3H, t).

[0192] This compound 236: 1 H-NMR (CDCl3) δ: 8.26 (1H, s), 7.18-7.09 (1H, m), 6.89-6.82 (1H, m), 6.69-6.62 (1H, m), 3.78-3.70 (1H, m), 2.44 (3H, s), 1.34-1.19 (4H, m).

[0193] Specific examples of the compound of the present invention are shown below, in which the symbols (III-1) to (III-16) each represent the following groups.

[0194] In the examples below, the symbol III-1 represents the following group: [wherein ● represents a bonding site, q represents an integer of 0 to 5, and the number written near the carbon atom represents G 1 Here, when q is an integer of 1 to 5, that is, when the phenyl group in III-1 is substituted with q substituents G 1 When substituted with, G in [Table 1A] to [Table 67A] and [Table 1-1] 1 In the above section, the substitution position is written before the symbol of the substituent.

[0195] In the examples below, the symbol III-2 represents the following group: [In the formula, ● represents a bonding site, r represents an integer of 0 to 5, and the number written near a carbon atom represents G 4 Here, when r is an integer of 1 to 5, that is, when the phenyl group in III-2 is substituted with r substituents G 4 When substituted with, G in [Table 1A] to [Table 67A] and [Table 1-2] 4 In the above section, the substitution position is written before the symbol of the substituent.

[0196] In the examples below, the symbols III-3, III-4, III-5, and III-6 represent the following groups. [wherein ● represents a bonding site, q represents an integer of 0 to 5, and the number written near the carbon atom represents G 1 Here, when q is an integer of 1 to 5, that is, when the 5- or 6-membered aromatic heterocyclic group in III-3, III-4, III-5, or III-6 is a group having q substituents G 1 When substituted with, G in [Table 1A] to [Table 67A] and [Table 1-1] 1 In the above section, the substitution position is written before the symbol of the substituent.

[0197] In the following examples, the symbols III-7, III-8, III-9, III-10, III-11, III-12, III-13, and III-14 represent the following 5- or 6-membered aromatic heterocyclic groups. [In the formula, ● represents a bonding site, r represents an integer of 0 to 5, and the number written near a carbon atom represents G 4 Here, when r is an integer of 1 to 5, that is, when the groups in III-7, III-8, III-9, III-10, III-11, III-12, III-13, and III-14 are substituted with r substituents G 4 When substituted with, G in [Table 1A] to [Table 67A] and [Table 1-2] 4 In the above section, the substitution position is written before the symbol of the substituent.

[0198] In the examples below, symbols III-15 and III-16 represent the following fused ring groups. [In the formula, ● represents a bonding site, r represents an integer of 0 to 5, and the number written near a carbon atom represents G 4 Here, when r is an integer of 1 to 5, that is, when the groups in III-15 and III-16 are substituted with r substituents G 4 When substituted with, G in [Table 1A] to [Table 67A] and [Table 1-2] 4 In the above section, the substitution position is written before the symbol of the substituent.

[0199] In the following examples, s ＊ 1 to s ＊ The symbol 96 is R listed in [Table 1-1]. １ The group is shown.

[0200] In the following examples, t ＊ 1 to t ＊ The symbol 155 is R listed in [Table 1-2]. ３ The group is shown.

[0201]

[0202]

[0203] Formula (IA) In this case, R 1 and R 3, and q and G in III-1 1 , r and G in III-2 4 The combination of is any one of the combinations described in [Table 1A] to [Table 67A] (hereinafter referred to as compound group SX1).

[0204] Here, in formula (IA), R 1 and R 3 However, the compound having the combination No. 2 in Table 1A is specifically a compound having the following structure:

[0205] Formula (IB) In this case, R 1 and R 3 , and q and G in III-1 1 , r and G in III-2 4 The combination of is any one of the combinations described in [Table 1A] to [Table 67A] (hereinafter referred to as compound group SX2).

[0206] Formula (IC) In this case, R 1 and R 3 , and q and G in III-1 1 , r and G in III-2 4 The combination of is any one of the combinations described in [Table 1A] to [Table 67A] (hereinafter referred to as compound group SX3).

[0207] Formula (ID) In this case, R 1 and R 3 , and q and G in III-1 1 , r and G in III-2 4 The combination of is any one of the combinations described in [Table 1A] to [Table 67A] (hereinafter referred to as compound group SX4).

[0208] Formula (IE) In this case, R 1 and R 3 , and q and G in III-1 1 , r and G in III-2 4The combination of is any one of the combinations described in [Table 1A] to [Table 67A] (hereinafter referred to as compound group SX5).

[0209] Formula (IF) In this case, R 1 and R 3 , and q and G in III-1 1 , r and G in III-2 4 The combination of is any one of the combinations described in [Table 1A] to [Table 67A] (hereinafter referred to as compound group SX6).

[0210] Formula (IG) In this case, R 1 and R 3 , and q and G in III-1 1 , r and G in III-2 4 The combination of is any one of the combinations described in [Table 1A] to [Table 67A] (hereinafter referred to as compound group SX7).

[0211] Formula (IH) In this case, R 1 and R 3 , and q and G in III-1 1 , r and G in III-2 4 The combination of is any one of the combinations described in [Table 1A] to [Table 67A] (hereinafter referred to as compound group SX8).

[0212] Formula (II) In this case, R 1 and R 3 , and q and G in III-1 1 , r and G in III-2 4 The combination of is any one of the combinations described in [Table 1A] to [Table 67A] (hereinafter referred to as compound group SX9).

[0213] Formula (I-J) In this case, R 1 and R 3 , and q and G in III-1 1 , r and G in III-2 4The combination of is any of the combinations described in [Table 1A] to [Table 67A] (hereinafter referred to as compound group SX10).

[0214] Formula (I-K) In this case, R 1 and R 3 , and q and G in III-1 1 , r and G in III-2 4 The combination of is any one of the combinations described in [Table 1A] to [Table 67A] (hereinafter referred to as compound group SX11).

[0215] Formula (IL) In this case, R 1 and R 3 , and q and G in III-1 1 , r and G in III-2 4 The combination of is any of the combinations described in [Table 1A] to [Table 67A] (hereinafter referred to as compound group SX12).

[0216] In formula (IA), R 1 and R 3 The combination of is any of the combinations described in [Table 1B] to [Table 204B] (hereinafter referred to as compound group SX13).

[0217] In formula (IB), R 1 and R 3 The combination of is any of the combinations described in [Table 1B] to [Table 204B] (hereinafter referred to as compound group SX14).

[0218] In formula (IC), R 1 and R 3 The combination of is any of the combinations described in [Table 1B] to [Table 204B] (hereinafter referred to as compound group SX15).

[0219] In formula (ID), R 1 and R 3 The combination of is any of the combinations described in [Table 1B] to [Table 204B] (hereinafter referred to as compound group SX16).

[0220] In formula (IE), R 1 and R3 The combination of is any of the combinations described in [Table 1B] to [Table 204B] (hereinafter referred to as compound group SX17).

[0221] In formula (IF), R 1 and R 3 The combination of is any of the combinations described in [Table 1B] to [Table 204B] (hereinafter referred to as compound group SX18).

[0222] In formula (IG), R 1 and R 3 The combination of is any of the combinations described in [Table 1B] to [Table 204B] (hereinafter referred to as compound group SX19).

[0223] In formula (I-H), R 1 and R 3 The combination of is any of the combinations described in [Table 1B] to [Table 204B] (hereinafter referred to as compound group SX20).

[0224] In formula (II), R 1 and R 3 The combination of is any of the combinations described in [Table 1B] to [Table 204B] (hereinafter referred to as compound group SX21).

[0225] In formula (I-J), R 1 and R 3 The combination of is any of the combinations described in [Table 1B] to [Table 204B] (hereinafter referred to as compound group SX22).

[0226] In formula (I-K), R 1 and R 3 The combination of is any of the combinations described in [Table 1B] to [Table 204B] (hereinafter referred to as compound group SX23).

[0227] In formula (IL), R 1 and R 3 The combination of is any of the combinations described in [Table 1B] to [Table 204B] (hereinafter referred to as compound group SX24).

[0228] The symbol "#" in the column for A in [Table 1A] to [Table 67A] and [Table 1B] to [Table 204B] indicates that A is a single bond.

[0229] G in [Table 1] to [Table 67A], [Table 1-1] and [Table 1-2] １ or G ４ The symbol "-" in the section 1 or R 3 indicates that the group is unsubstituted.

[0230] Here, in formula (IA), R 1 and R 3 However, the compounds having the combinations of Nos. 1-140 shown in Table 3B are specifically compounds having the following structures:

[0231]

[0232]

[0233]

[0234]

[0235]

[0236]

[0237]

[0238]

[0239]

[0240]

[0241]

[0242]

[0243]

[0244]

[0245]

[0246]

[0247]

[0248]

[0249]

[0250]

[0251]

[0252]

[0253]

[0254]

[0255]

[0256]

[0257]

[0258]

[0259]

[0260]

[0261]

[0262]

[0263]

[0264]

[0265]

[0266]

[0267]

[0268]

[0269]

[0270]

[0271]

[0272]

[0273]

[0274]

[0275]

[0276]

[0277]

[0278]

[0279]

[0280]

[0281]

[0282]

[0283]

[0284]

[0285]

[0286]

[0287]

[0288]

[0289]

[0290]

[0291]

[0292]

[0293]

[0294]

[0295]

[0296]

[0297]

[0298]

[0299]

[0300]

[0301]

[0302]

[0303]

[0304]

[0305]

[0306]

[0307]

[0308]

[0309]

[0310]

[0311]

[0312]

[0313]

[0314]

[0315]

[0316] Formulation examples of the compounds of the present invention are shown below. Note that "parts" means "parts by weight." Compound S of the present invention represents a compound described in compound groups SX1 to SX24 and compounds 1 to 236 of the present invention.

[0317] Formulation Example 1 35 parts of a mixture of polyoxyethylene alkyl ether sulfate ammonium salt and silica (weight ratio 1:1), 10 parts of any one of the present compound S, and 55 parts of water are mixed and finely pulverized by a wet pulverization method to obtain a formulation.

[0318] Formulation Example 2 50 parts of any one of the present invention compounds S, 3 parts of calcium lignosulfonate, 2 parts of sodium lauryl sulfate, and 45 parts of silica are ground and mixed to obtain a formulation.

[0319] Formulation Example 3 A formulation is obtained by mixing 5 parts of any one of the present compound S, 9 parts of polyoxyethylene styrylphenyl ether, 5 parts of polyoxyethylene decyl ether (number of ethylene oxide added: 5), 6 parts of calcium dodecylbenzenesulfonate, and 75 parts of xylene.

[0320] Formulation Example 4: 2 parts of any one of the present compound S, 1 part of silica, 2 parts of calcium lignosulfonate, 30 parts of bentonite, and 65 parts of kaolin clay are pulverized and mixed, an appropriate amount of water is added, the mixture is kneaded, granulated in a granulator, and then dried to obtain a formulation.

[0321] Formulation Example 5 10 parts of any one of the present compound S is mixed with a mixture of 18 parts of benzyl alcohol and 9 parts of DMSO, and 6.3 parts of GERONOL (registered trademark) TE250, 2.7 parts of Ethylan (registered trademark) NS-500LQ, and 54 parts of solvent naphtha are added thereto and mixed to obtain a formulation.

[0322] The herbicidal activity of the compounds of the present invention is demonstrated by test examples. In the test examples below, the herbicidal activity is evaluated on an 11-point scale from 0 to 10, with "0" being assigned to a case where there is no or almost no difference in the state of emergence or growth of the test weeds at the time of the survey compared to that of an untreated plot, and "10" being assigned to a case where the test weeds are completely dead or where emergence or growth is completely suppressed. An untreated plot refers to a plot where the same procedures as the treated plot are carried out except that the test compound is not used.

[0323] Test Method 1: Post-emergence foliar treatment test in upland fields. Pots were filled with commercially available potting soil, and crabgrass (Digitaria ciliaris) seeds were sown and grown in a greenhouse until the 2-3 leaf stage. A predetermined amount of the test compound was then dissolved in 1 mL of dimethylformamide (DMF) solution containing 2% Polysorbate 20 (MP Biomedicals), to which 18 mL of water was added to prepare a diluted solution. The diluted solution was sprayed evenly over the plants to achieve the desired treatment dose. The plants were then grown in a greenhouse for 20 days, and the herbicidal efficacy was evaluated.

[0324] Test Example 1-1: The predetermined amount was 19 mg (processing amount 1,000 g / 10,000 m 2 ) and the following compounds of the present invention were used as test compounds, and tests were carried out according to Test Method 1. As a result, all of the following compounds of the present invention showed herbicidal efficacy of 8 or more. Compounds of the present invention: 1, 2, 3, 8, 9, 11, 12, 13, 23, 24, 25, 26, 27, 28, 32, 33, 34, 38, 39, 46, 48, 49, 50, 53, 55, 56, 65, 75, 76, 79, 97, 104, 105, 108, 110, 112, 113, 114, 120, 123, 127, 128, 129, 136, 138, 140, 141, 144, 145, 146, 148, 153, 154, 158, 161, 168, 169, 170, 172, 176, 177, 178, 179, 184, 185, 186, 187, 190, 191, 192, 195, 198, 204, 206, 208, 209, 210, 211, 217, 220, 222, 225, 228, 229, 230

[0325] Test Example 1-2: Instead of crabgrass, barnyard grass (Echinochloa crus-galli) was used, and the prescribed amount was 19 mg (treatment amount 1,000 g / 10,000 m 2) and the following compounds of the present invention were used as test compounds in accordance with Test Method 1. As a result, all of the following compounds of the present invention showed herbicidal efficacy of 8 or more. Compounds of the present invention: 1, 2, 3, 11, 12, 13, 23, 24, 25, 26, 27, 28, 32, 33, 34, 38, 39, 49, 65, 67, 76, 79, 97, 104, 105, 108, 110, 112, 113, 114, 120, 123, 127, 128, 129, 136, 138, 140, 141, 144, 145 , 146, 148, 153, 154, 158, 161, 168, 169, 170, 172, 176, 177, 178, 179, 184, 185, 186, 187, 190, 191, 192, 195, 198, 204, 206, 208, 209, 210, 211, 217, 220, 222, 225, 228, 229, 230

[0326] Test Example 1-3: Lolium multiflorum was used instead of crabgrass, and the prescribed amount was 19 mg (treatment amount 1,000 g / 10,000 m 2 ) and the following compounds of the present invention were used as test compounds, and tests were carried out according to Test Method 1. As a result, all of the following compounds of the present invention showed herbicidal efficacy of 8 or more. Compounds of the present invention: 1, 28, 33, 39, 76, 97, 104, 105, 107, 108, 110, 112, 113, 114, 115, 120, 123, 124, 125, 127, 128, 129, 132, 136, 138, 140, 144, 145, 146, 147, 148, 154, 158, 161, 168, 169, 170, 1 72, 176, 177, 178, 179, 180, 181, 184, 185, 186, 187, 188, 189, 190, 191, 192, 193, 198, 203, 204, 205, 206, 208, 209, 210, 211, 213, 215, 217, 220, 222, 225, 226, 227, 228, 229, 230, 231

[0327] Test Method 2: Post-emergence foliar treatment test in upland fields. Pots were filled with commercially available potting soil, and goosegrass (Eleusine indica) seeds were sown and grown in a greenhouse until the 2-3 leaf stage. A predetermined amount of the test compound was then dissolved in 0.95 mL of a DMF solution containing 2% Polysorbate 20 (MP Biomedicals), to which 8.6 mL of water was added to prepare a diluted solution. The diluted solution was sprayed evenly over the plants to achieve the desired treatment dose. The plants were then grown in a greenhouse for 20 days, and the herbicidal efficacy was evaluated.

[0328] Test Example 2-1: The predetermined amount was 2.375 mg (processing amount 125 g / 10,000 m 2 The following compounds of the present invention were used as test compounds in accordance with Test Method 2, and all of the compounds of the present invention showed herbicidal efficacy of 8 or higher. Compounds of the present invention: 1, 2, 25, 38, 97, 110, 129, 136, 206

[0329] Test Example 2-2: Instead of goosegrass, large crabgrass (Digitaria insularis) was used, and the prescribed amount was 2.375 mg (treatment amount 125 g / 10,000 m 2 ) and the following compounds of the present invention were used as test compounds in accordance with Test Method 2. As a result, all of the following compounds of the present invention showed herbicidal efficacy of 8 or more. Compounds of the present invention: 1, 2, 8, 25, 27, 28, 33, 34, 38, 46, 94, 97, 112, 113, 114, 128, 129, 136, 138, 144, 158, 168, 189, 193, 203, 204, 206

[0330] The compound of the present invention has excellent control activity against weeds.

Claims

1. Formula (I) [In the formula, R 1 is the group G 1 a phenyl group optionally substituted with one or more substituents selected from the group G 1 R represents a 5- or 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from the group consisting of 2 is the group G 2 a C1-C8 chain hydrocarbon group optionally substituted with one or more substituents selected from the group G 3 a C3-C8 alicyclic hydrocarbon group optionally substituted with one or more substituents selected from the group consisting of a halogen atom, a cyano group, OR 10 , C (= Z 1 ) R 11 , C (= Z 1 ) OR 12 , C (= Z 1 ) NR 11 R 12 , mercapto group, S(O) p R 13 , or NR 11 R 14 p represents 0, 1, or 2; R 3 is the group G 4 a phenyl group optionally substituted with one or more substituents selected from the group G 4 a 5- or 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from the group G 4 a group represented by formula B1, or a group represented by formula B2 (● represents a bonding site to a nitrogen atom), which may be substituted by one or more substituents selected from the group consisting of: G ７ａ , G ７ｂ and G ７ｃ The combination of ７ａ is C=O or CR ３０ａ R ３１ａ and G ７ｂ is C=O or CR ３０ｂ R ３１ｂ and G ７ｃ is C=O or CR ３０ｃ R ３１ｃ A combination where ７ａ is C=O or CR ３０ａ R ３１ａ and G ７ｂ is C=O or CR ３０ｂ R ３１ｂ and G ７ｃ is NR ３２ｃ , an oxygen atom, a sulfur atom, S═O, or S═O ２ A combination where ７ａ is C=O or CR ３０ａ R ３１ａ and G ７ｂ is NR ３２ｂ , an oxygen atom, a sulfur atom, S═O, or S═O ２ and G ７ｃ is C=O or CR ３０ｃ R ３１ｃ A combination where ７ａ is NR ３２ａ , an oxygen atom, a sulfur atom, S═O, or S═O ２ and G ７ｂ is C=O or CR ３０ｂ R ３１ｂ and G ７ｃ is C=O or CR ３０ｃ R ３１ｃ or a combination in which ７ａ is NR ３２ａ , an oxygen atom, a sulfur atom, S═O, or S═O ２ and G ７ｂ is C=O or CR ３０ｂ R ３１ｂ and G ７ｃ is NR ３２ｃ , an oxygen atom, a sulfur atom, S═O, or S═O ２ A combination in which ７ｄ , G ７ｅ , G ７ｆ and G ７ｇ The combination of ７ｄ is C=O or CR ３０ｄ R ３１ｄ and G ７ｅ is C=O or CR ３０ｅ R ３１ｅ and G ７ｆ is C=O or CR ３０ｆ R ３１ｆ and G ７ｇ is C=O or CR ３０ｇ R ３１ｇ A combination where ７ｄ is C=O or CR ３０ｄ R ３１ｄ and G ７ｅ is C=O or CR ３０ｅ R ３１ｅ and G ７ｆ is C=O or CR ３０ｆ R ３１ｆ and G ７ｇ is NR ３２ｇ , an oxygen atom, a sulfur atom, S═O, or S═O ２ A combination where ７ｄ is C=O or CR ３０ｄ R ３１ｄ and G ７ｅ is C=O or CR ３０ｅ R ３１ｅ and G ７ｆ is NR ３２ｆ , an oxygen atom, a sulfur atom, S═O, or S═O ２ and G ７ｇ is C=O or CR ３０ｇ R ３１ｇ A combination where ７ｄ is C=O or CR ３０ｄ R ３１ｄ and G ７ｅ is NR ３２ｅ , an oxygen atom, a sulfur atom, S═O, or S═O ２ and G ７ｆ is C=O or CR ３０ｆ R ３１ｆ and G ７ｇ is C=O or CR ３０ｇ R ３１ｇ A combination where ７ｄ is C=O or CR ３０ｄ R ３１ｄ and G ７ｅ is NR ３２ｅ , an oxygen atom, a sulfur atom, S═O, or S═O ２ and G ７ｆ is C=O or CR ３０ｆ R ３１ｆ and G ７ｇ is NR ３２ｇ , an oxygen atom, a sulfur atom, S═O, or S═O ２ A combination where ７ｄ is NR ３２ｄ , an oxygen atom, a sulfur atom, S═O, or S═O ２ and G ７ｅ is C=O or CR ３０ｅ R ３１ｅ and G ７ｆ is C=O or CR ３０ｆ R ３１ｆ and G ７ｇ is C=O or CR ３０ｇ R ３１ｇ A combination where ７ｄ is NR ３２ｄ , an oxygen atom, a sulfur atom, S═O, or S═O ２ and G ７ｅ is C=O or CR ３０ｅ R ３１ｅ and G ７ｆ is C=O or CR ３０ｆ R ３１ｆ and G ７ｇ is NR ３２ｇ , an oxygen atom, a sulfur atom, S═O, or S═O ２ or a combination in which ７ｄ is NR ３２ｄ , an oxygen atom, a sulfur atom, S═O, or S═O ２ and G ７ｅ is C=O or CR ３０ｅ R ３１ｅ and G ７ｆ is NR ３２ｆ , an oxygen atom, a sulfur atom, S═O, or S═O ２ and G ７ｇ is C=O or CR ３０ｇ R ３１ｇ A combination where X 1 and X 2 are the same or different and represent an oxygen atom or a sulfur atom; Y 1 is OR 15 or SR 15 m and n are the same or different and represent 0, 1, or 2; A is a single bond, an oxygen atom, a sulfur atom, —S(O)—, —S(O)2—, or —CR 4 R 5 -, -C (=Z 4 ) - or -NR 6 represents -, R 4 and R 5 are the same or different and represent a C1-C3 alkyl group optionally substituted with one or more halogen atoms, a C1-C3 alkoxy group optionally substituted with one or more halogen atoms, a hydroxy group, or a hydrogen atom, or 4 and R 5 and together form a C2-C5 alkylene group, or —O(CH2) q O—, q represents 2, 3 or 4, Z 4 represents an oxygen atom, a sulfur atom, or CH; R 6 represents a C1-C3 alkyl group optionally substituted with one or more halogen atoms, C(=Z 5 ) R 34 Group, C (=Z 5 ) OR 34 group or a hydrogen atom; Z 1 , Z 2 , Z 3 , and Z 5 are the same or different and represent an oxygen atom or a sulfur atom; R 10 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, a C3-C6 alicyclic hydrocarbon group optionally substituted with one or more halogen atoms, or a group G 6 R represents a phenyl group which may be substituted with one or more substituents selected from the group consisting of 11 , R 21 , and R 26 are the same or different and represent a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, a C3-C6 alicyclic hydrocarbon group optionally substituted with one or more halogen atoms, a group G 6 R represents a phenyl group which may be substituted with one or more substituents selected from the group consisting of: 12 , R 20 , R 22 , R 25 , and R 27 are the same or different and represent a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, a C3-C6 alicyclic hydrocarbon group optionally substituted with one or more halogen atoms, or a hydrogen atom; R 13 , R 23 , and R 28 are the same or different and represent a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, a C3-C6 alicyclic hydrocarbon group optionally substituted with one or more halogen atoms, or a group G 6 R represents a phenyl group which may be substituted with one or more substituents selected from the group consisting of 14 , R 24 , R 29 , and R 34 are the same or different and represent a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, or a C3-C6 alicyclic hydrocarbon group optionally substituted with one or more halogen atoms, R 35 and R 36 together with the nitrogen atom to which they are bonded, represent a saturated or unsaturated 5- or 6-membered cyclic amino group {the cyclic amino group may be substituted with one or more substituents selected from the group consisting of a C1-C3 alkyl group optionally substituted with one or more halogen atoms, and a halogen atom}, R 15 is the group G ８ a C1-C10 chain hydrocarbon group optionally substituted with one or more substituents selected from the group consisting of a C3-C6 alicyclic hydrocarbon group optionally substituted with one or more halogen atoms, a benzyl group {the phenyl moiety in the benzyl group is selected from the group G ６ and the methylene portion may be substituted with one or two C1-C3 alkyl groups}, or a hydrogen atom; R ３０ａ 、 R ３０b 、 R ３０c , R ３０d 、 R ３０e 、 R ３０f 、 R ３０g 、 R ３１ａ , R ３１b 、 R ３１c , R ３１d 、 R ３１e 、 R ３１f 、 and R ３１g are the same or different and represent a C1-C6 alkyl group optionally substituted with one or more halogen atoms, a halogen atom, or a hydrogen atom; R ３２ａ 、 R ３２b 、 R ３２c , R ３２d 、 R ３２e 、 R ３２f 、 and R ３２g are the same or different and represent a C1-C6 alkyl group optionally substituted with one or more halogen atoms, a (C1-C3 alkyl)carbonyl group optionally substituted with one or more halogen atoms, or a hydrogen atom; R ３３ａ 、 R ３３b 、 R ３３c , R ３３d 、 R ３３e 、 and R ３３f are the same or different and represent a C1-C3 alkyl group optionally substituted with one or more halogen atoms, a halogen atom, or a hydrogen atom. 1 : a C1-C3 alkyl group optionally substituted with one or more halogen atoms, group G １－１ a C3-C6 cycloalkyl group optionally substituted by one or more substituents selected from the group consisting of: OR 20 Group, C (=Z 2 ) R 21 Group, C (=Z 2 ) OR 22 Group, C (=Z 2 ) NR 21 R 22 group, mercapto group, S(O) n R 23 group, NR 20 R 24 Group G consisting of a nitro group, a halogen atom, and a cyano group. 1-1 Group G: a group consisting of a halogen atom and a cyano group. 2 Group G: a group consisting of a C1-C3 alkoxy group optionally substituted with one or more halogen atoms, a C1-C3 alkylthio group optionally substituted with one or more halogen atoms, a C1-C3 alkylsulfinyl group optionally substituted with one or more halogen atoms, a C1-C3 alkylsulfonyl group optionally substituted with one or more halogen atoms, a halogen atom, a cyano group, a hydroxy group, and a mercapto group. 3 Group G: a group consisting of a C1-C3 alkyl group optionally substituted with one or more halogen atoms, a C1-C3 alkoxy group optionally substituted with one or more halogen atoms, a C1-C3 alkylthio group optionally substituted with one or more halogen atoms, a C1-C3 alkylsulfinyl group optionally substituted with one or more halogen atoms, a C1-C3 alkylsulfonyl group optionally substituted with one or more halogen atoms, an oxo group, a thioxo group, a halogen atom, a cyano group, a hydroxy group, and a mercapto group. 4 :Group G ４－2 a C1-C6 alkyl group optionally substituted with one or more substituents selected from the group G ４－１ a C3-C6 cycloalkyl group optionally substituted by one or more substituents selected from the group consisting of: OR ２５ Group, C (=Z ３ ) R ２６ Group, C (=Z ３ ) OR ２７ Group, C (=Z ３ ) NR ２６ R27 group, mercapto group, S(O) ｍ R ２８ group, NR ２５ R ２９ group, NR ３５ R ３６ group, nitro group, halogen atom, SF ５ Group G consisting of a cyano group, a morpholino group, and a cyano group. 6 Group G: a group consisting of a C1-C3 alkoxy group optionally substituted with one or more halogen atoms, a C1-C3 alkylthio group optionally substituted with one or more halogen atoms, a C1-C3 alkylsulfinyl group optionally substituted with one or more halogen atoms, a C1-C3 alkylsulfonyl group optionally substituted with one or more halogen atoms, a halogen atom, a cyano group, a nitro group, a hydroxy group, and a mercapto group. ４－１ C1-C6 chain hydrocarbon group, C1-C6 alkoxy group, C1-C6 alkylthio group, C1-C6 alkylamino group, C2-C8 dialkylamino group, (C1-C6 alkyl)carbonyl group, (C1-C6 alkoxy)carbonyl group, (C1-C6 alkylamino)carbonyl group, (C2-C8 dialkylamino)carbonyl group, C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, (C1-C6 alkylamino)sulfonyl group, (C2-C8 dialkylamino)sulfonyl group {the C1-C6 chain hydrocarbon group The hydrogen hydride group, the C1-C6 alkoxy group, the C1-C6 alkylthio group, the C1-C6 alkylamino group, the C2-C8 dialkylamino group, the (C1-C6 alkyl)carbonyl group, the (C1-C6 alkoxy)carbonyl group, the (C1-C6 alkylamino)carbonyl group, the (C2-C8 dialkylamino)carbonyl group, the C1-C6 alkylsulfinyl group, the C1-C6 alkylsulfonyl group, the (C1-C6 alkylamino)sulfonyl group, and the (C2-C8 dialkylamino)sulfonyl group are each selected from the group G 4-1-1 and optionally substituted with one or more substituents selected from the group consisting of a halogen atom, a cyano group, a nitro group, a hydroxy group, an amino group, a formyl group, an aminocarbonyl group, an aminosulfonyl group, and SF ５ Group G ４－２ a C1-C6 alkoxy group, a C1-C6 alkylthio group, a C1-C6 alkylamino group, a C2-C8 dialkylamino group, a (C1-C6 alkyl)carbonyl group, a (C1-C6 alkoxy)carbonyl group, a (C1-C6 alkylamino)carbonyl group, a (C2-C8 dialkylamino)carbonyl group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group, a (C1-C6 alkylamino)sulfonyl group, a (C2-C8 dialkylamino)sulfonyl group {said C1-C6 alkoxy group, a C1-C6 alkylthio group, a C1-C6 alkylamino group, a C2-C8 dialkylamino group, a (C1-C6 alkyl)carbonyl group, a (C1-C6 alkoxy)carbonyl group, a (C1-C6 alkylamino)carbonyl group, a (C2-C8 dialkylamino)carbonyl group {said C1-C6 alkoxy group, a C1-C6 alkylthio group, a C1-C6 alkylamino group, a C2-C8 dialkylamino group, a (C1-C6 alkyl)carbonyl group, a (C1-C6 alkylamino)sulfonyl group, a (C2-C8 dialkylamino)sulfonyl group {said C1-C6 alkoxy group, a C1-C6 alkylthio ... The alkoxy group, the C1-C6 alkylthio group, the C1-C6 alkylamino group, the C2-C8 dialkylamino group, the (C1-C6 alkyl)carbonyl group, the (C1-C6 alkoxy)carbonyl group, the (C1-C6 alkylamino)carbonyl group, the (C2-C8 dialkylamino)carbonyl group, the C1-C6 alkylsulfinyl group, the C1-C6 alkylsulfonyl group, the (C1-C6 alkylamino)sulfonyl group, and the (C2-C8 dialkylamino)sulfonyl group are each selected from the group G 4-1-1 and optionally substituted with one or more substituents selected from the group consisting of a halogen atom, a cyano group, a nitro group, a hydroxy group, an amino group, a formyl group, an aminocarbonyl group, an aminosulfonyl group, and SF ５ Group G 4-1-1 Group G: A group consisting of halogen atoms, cyano groups, nitro groups, hydroxy groups, amino groups, oxo groups, thioxo groups, aminocarbonyl groups, aminosulfonyl groups, C3-C6 cycloalkyl groups, C1-C3 alkoxy groups, C1-C3 alkylthio groups, (C1-C3 alkyl)carbonyl groups, (C1-C3 alkoxy)carbonyl groups, C1-C3 alkylsulfinyl groups, and C1-C3 alkylsulfonyl groups (the C3-C6 cycloalkyl groups, the C1-C3 alkoxy groups, the C1-C3 alkylthio groups, the (C1-C3 alkoxy)carbonyl groups, the C1-C3 alkylsulfinyl groups, and the C1-C3 alkylsulfonyl groups are optionally substituted with one or more halogen atoms). ８ or a salt thereof.] 2. R 3 But the group G 4 a phenyl group optionally substituted with one or more substituents selected from the group G 4 R is a 5- or 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from 15 a C1-C10 chain hydrocarbon group optionally substituted with one or more halogen atoms, a C3-C6 alicyclic hydrocarbon group optionally substituted with one or more halogen atoms, a benzyl group {the phenyl moiety in the benzyl group is selected from the group G 6 and the methylene portion may be substituted with one or two C1-C3 alkyl groups} or a hydrogen atom; 1 is a C1-C3 alkyl group optionally substituted with one or more halogen atoms, a C3-C6 cycloalkyl group, OR 20 Group, C (=Z 2 ) R 21 Group, C (=Z 2 ) OR 22 Group, C (=Z 2 ) NR 21 R 22 group, mercapto group, S(O) n R 23 group, NR 20 R 24 group, a nitro group, a halogen atom, and a cyano group; 4 is a C1-C3 alkyl group optionally substituted with one or more halogen atoms, a C3-C6 cycloalkyl group, OR 25 Group, C (=Z 3 ) R 26 Group, C (=Z 3 ) OR 27 Group, C (=Z 3 ) NR 26 R 27 group, mercapto group, S(O) m R 28 group, NR 25 R 29 The compound or salt thereof according to claim 1 , wherein the group consisting of a nitro group, a halogen atom, and a cyano group.

3. X 1 and X 2 The compound or salt thereof according to claim 1 or 2, wherein is an oxygen atom.

4. Y 1 is OR 15 The compound or salt thereof according to any one of claims 1 to 3, wherein the compound is a group.

5. R 2 is a C1-C3 alkyl group optionally substituted with one or more halogen atoms, or a C3-C6 cycloalkyl group optionally substituted with one or more halogen atoms, or a salt thereof.

6. R 1 But the group G 1 6. The compound or salt thereof according to any one of claims 1 to 5, wherein the phenyl group is a phenyl group optionally substituted with one or more substituents selected from the following:

7. R １ But the group G 1 In the 5-6 membered aromatic heterocyclic group, the atom bonded to A is a carbon atom, and A is an oxygen atom or -CR 4 R 5 The compound or salt thereof according to any one of claims 1 to 5, wherein 8. R １ But the group G 1 In the 5-membered aromatic heterocyclic group, the atom bonded to A is a nitrogen atom, and A is -CR 4 R 5 The compound or salt thereof according to any one of claims 1 to 5, wherein 9. R １ But the group G １ The compound or salt thereof according to any one of claims 1 to 5, wherein A is a 5- or 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from the group consisting of:

10. Group G １ is the group consisting of a C1-C3 alkyl group optionally substituted with one or more halogen atoms, a C1-C3 alkoxy group optionally substituted with one or more halogen atoms, a C1-C3 alkylthio group optionally substituted with one or more halogen atoms, a C3-C6 cycloalkyl group, a halogen atom, a nitro group, and a cyano group.

11. The compound or salt thereof according to any one of claims 1 to 7 or 10, wherein A is -CH2-.

12. The compound or salt thereof according to any one of claims 1 to 6 or 10, wherein A is a single bond.

13. The compound or salt thereof according to any one of claims 1 to 7 or 10, wherein A is an oxygen atom.

14. R 3 But the group G 4 a phenyl group optionally substituted with 1 to 3 substituents selected from the group G 4 The compound or salt thereof according to any one of claims 1 to 13, which is a 5- or 6-membered aromatic heterocyclic group optionally substituted with 1 to 3 substituents selected from the following:

15. R ３ But the group G ４ The compound or salt thereof according to any one of claims 1 to 14, wherein the phenyl group is optionally substituted with 1 to 3 substituents selected from the group consisting of:

16. R ３ But the group G ４ The compound or salt thereof according to any one of claims 1 to 14, which is a 5- or 6-membered aromatic heterocyclic group optionally substituted with 1 to 3 substituents selected from the following:

17. R ３ But the group G ４ 17. The compound or salt thereof according to any one of claims 1 to 14 or 16, wherein the compound is a 5-membered aromatic heterocyclic group optionally substituted with 1 to 3 substituents selected from the following:

18. R ３ is a 5-membered aromatic heterocyclic group represented by formula D-1 or D-2 [wherein ● represents a bonding site with a nitrogen atom, G １０ａ , G １０ｂ , G １０ｃ , G １０ｄ , G １０ｅ , and G １０ｆ are the same or different and represent a nitrogen atom or a group G ４ R represents a methine group optionally substituted with a substituent selected from the group consisting of ３７ａ , and R ３７ｂ and are the same or different and represent a C1-C3 alkyl group optionally substituted with one or more halogen atoms, a C3-C6 cycloalkyl group optionally substituted with one or more halogen atoms, or a hydrogen atom.

19. R ３ But the group G ４ The compound or salt thereof according to any one of claims 1 to 14 or 16, which is a 6-membered aromatic heterocyclic group optionally substituted with 1 to 3 substituents selected from the following:

20. R ３ But the group G ４ 20. The compound or salt thereof according to any one of claims 1 to 14, 16, or 19, which is a pyridyl group optionally substituted with 1 to 3 substituents selected from the following:

21. R ３ is a group represented by formula B1-1 or a group represented by formula B2-1 [wherein ● represents a bonding site with a nitrogen atom, R ３３ａ 、 R ３３b 、 R ３３c , R ３３d 、 R ３３e 、 and R ３３f are the same or different and represent a C1-C3 alkyl group optionally substituted with one or more halogen atoms, a halogen atom, or a hydrogen atom; G ７ａ1 , G ７ｃ1 , G ７ｄ1 , and G ７g1 are the same or different and represent an oxygen atom or a sulfur atom; G ７b1 , G ７e1 , and G ７f1 represents a methylene group {the methylene group may be substituted with one or more substituents selected from the group consisting of a C1-C3 alkyl group optionally substituted with one or more halogen atoms, and a halogen atom}.

22. R ３ is a group represented by formula B1-2 [wherein ● represents a bonding site with a nitrogen atom, G ７ａ2 , and G ７ｃ2 are the same or different and represent an oxygen atom or a sulfur atom; ７b2 represents a methylene group {the methylene group may be substituted with one or more substituents selected from the group consisting of a C1-C3 alkyl group optionally substituted with one or more halogen atoms, and a halogen atom}.

23. Group G ４ is the group consisting of a C1-C3 alkyl group optionally substituted with one or more halogen atoms, a C1-C3 alkoxy group optionally substituted with one or more halogen atoms, a C1-C3 alkylthio group optionally substituted with one or more halogen atoms, a C1-C3 alkylsulfinyl group optionally substituted with one or more halogen atoms, a C1-C3 alkylsulfonyl group optionally substituted with one or more halogen atoms, a C3-C6 cycloalkyl group optionally substituted with one or more halogen atoms, a C3-C6 cycloalkyl group optionally substituted with a cyano group, a halogen atom, a nitro group, and a cyano group.

24. A herbicidal composition comprising the compound or salt thereof according to any one of claims 1 to 23 and an inert carrier.

25. A method for controlling weeds, comprising the step of applying the compound or salt thereof according to any one of claims 1 to 23 to weeds or soil in which weeds grow.

26. Use of a compound according to any one of claims 1 to 23 or a salt thereof for controlling weeds.

27. A composition comprising one or more components selected from the group consisting of group (d) and group (f), and the compound or salt thereof according to any one of claims 1 to 23: Group (d): phytotoxicity-reducing component; Group (f): herbicidal active component.

Images