Herbicidal compositions comprising difluorobutenamide compounds

Abstract

The present invention provides a difluorobutylene amide compound having an excellent control effect on harmful weeds, and a herbicidal composition thereof. A herbicidal composition containing, as an active ingredient, a difluorobutylene amide compound represented by formula (I) (wherein each symbol is as defined in the description) or a salt thereof has an excellent controlling effect on harmful weeds. # imgabs0 #

Description

Technical Field

[0001] The present invention relates to novel difluorobutenamide compounds or salts thereof, and herbicidal compositions containing them as active ingredients. Background Art

[0002] Patent Document 1 describes cinnamamide derivatives having herbicidal activity. However, Patent Document 1 does not describe a difluorocrotonamide compound having a substituent on a phenyl group and a C4-C5 alicyclic hydrocarbon represented by (I) below (hereinafter also referred to as a specific difluorocrotonamide compound).

[0003] Patent Document 2 describes aromatic-aliphatic carboxylic acid derivatives as drug damage reducing agents. However, Patent Document 2 does not describe the specific difluorocrotonamide compound represented by (I) below.

[0004] On the other hand, compounds such as 1-[{4-(3-fluorophenyl)-1-oxo-3-butyl-1-yl}amino]cyclopropanecarboxylic acid (CAS Registry No.: 1608641-02-6), cis-3-[{(3E)-4-(4-fluorophenyl)-1-oxo-3-butyl-1-yl}amino]cyclobutanecarboxylic acid (CAS Registry No.: 2026935-61-3), 3-[{4-(4-fluorophenyl)-1-oxo-3-butyl-1-yl}amino]cyclopentanecarboxylic acid (CAS Registry No.: 1608649-05-3) and N-[(1S,4R)-4-(hydroxymethyl)-2-cyclopenten-1-yl]-4-(4-methylphenyl)-3-butenamide (CAS Registry No.: 1808292-36-5) are known, but their uses are unknown. Of course, it is not known that these compounds have herbicidal activity.

[0005] Patent Document 3 and Non-Patent Document 1 describe methods for producing N-cyclohexyl-4-phenyl-2,2-difluoro-3-butenamide compounds.

[0006] A method for producing bicyclic amidines is described in Non-Patent Document 2. In the Supporting Information of Non-Patent Document 2, the physical property data of N-cyclohexyl-4-phenyl-2,2-difluoro-3-butenamide analogous compounds which are by-products of the cyclization reaction of Entry 9 in Table 1 are described.

[0007] However, there is no description of the control effect of the described compounds on undesirable plants or the effect of inhibiting the growth of undesirable plants in Patent Document 3, Non-Patent Document 1 and Non-Patent Document 2. Furthermore, there is no description of the specific difluorocrotonamide compound represented by (I) below.

[0008] Prior art literature

[0009] Patent Literature

[0010] Patent Document 1: China Patent Application Publication No. 109896973

[0011] Patent Document 2: International Publication No. 2005 / 016001

[0012] Patent Document 3: Chinese Patent Application Publication No. 113511972

[0013] Non-patent literature

[0014] Non-patent literature 1: European Journal Organic Chemistry 2021, 48, 6700-6704

[0015] Non-patent document 2: European Journal Organic Chemistry 2011, 36, 7317-7323 Summary of the invention

[0016] Problems to be solved by the invention

[0017] In order to save labor in the operation of preventing and controlling undesirable plants (hereinafter, also referred to as harmful weeds) and improve the productivity of agricultural and horticultural crops, it is desired to apply herbicides to soil, stems and leaves, etc., and show excellent control effects on harmful weeds at low dosages. In addition, it is expected that the environmental load (impact on surrounding plants and ecosystems) is small and the safety is high. The present invention provides a difluorobutylene amide compound and a herbicidal composition thereof having excellent control effects on harmful weeds and excellent safety for useful plants.

[0018] Means of solving the problem

[0019] The present inventors synthesized a specific difluorocrotonamide compound represented by (I) below, which had hitherto unknown herbicidal activity, and conducted in-depth studies on its herbicidal activity and usefulness. As a result, it was found that a composition containing the specific difluorocrotonamide compound represented by (I) below or a salt thereof as an active ingredient exhibited an excellent control effect on weeds. Furthermore, it was found that the compound of the present invention was excellent in safety to useful plants, thereby completing the present invention.

[0020] That is, the present invention relates to a method for controlling undesirable plants or inhibiting the growth of undesirable plants by applying an effective amount of a difluorocrotonamide compound represented by formula (I) or a salt thereof (hereinafter, also referred to as compound (I) or the compound of the present invention) to soil, wherein the compound (I) is applied to harmful weeds, useful plants, or soil in an effective amount.

[0021]

[0022] In the formula, R 1 and R 2 Each is a halogen, may be replaced by at least one Y 1 Substituted (C1-C6)-chain hydrocarbon radical, (C1-C6)-alkoxy radical which may be substituted by at least one halogen, cyano radical or H;

[0023] R 3 is H or fluorine atom, but excludes R 1 , R 2 and R 3 All are H cases;

[0024] Y 1 is halogen, (C1-C6)-alkoxy or cyano;

[0025] t is 1 or 2;

[0026] R 4 -C(=O)OR 5 、-C(=O)SR 6 、-C(=O)NR 7 R 8 、-C(=O)R 9 , can be at least one Z 3 Substituted (C1-C6)-chain hydrocarbon group, -C(=O)H, -N(R 10 )C(=O)R 11 、-SR 6 、-S(=O)R 6 、-S(=O)2R 6 , =CHC(=O)R 11 , cyano, OH, 1,3-dioxolan-2-yl, 2-thiazolyl, may be replaced by at least one Z 4 Substituted 2-imidazolyl, =CHCH=CHC(=O)R 11 、-(C=O)2R 11 、-C(=NR 11 )-C(=O)R 11 or -CH(OH)-C(=O)R 11 ;

[0027] R 5 can be represented by at least one Z 1 Substituted (C1-C6)-alkyl, H, (C3-C6)-cycloalkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl or a 4- to 6-membered oxygen-containing saturated heterocyclic ring;

[0028] Z 1is cyano, halogen, (C1-C6)-alkylthio, (C1-C6)-alkylsulfonyl, (C1-C6)-alkoxy, phenyl, pyridyl, (C1-C6)-alkoxycarbonyl, (C3-C6)-cycloalkyl, tert-butyldimethylsiloxy, OH, amino or 1,3-dioxolan-4-yl;

[0029] R 6 is (C1-C6)-alkyl, (C3-C6)-cycloalkyl or benzyl which may be substituted by at least one halogen;

[0030] R 7 can be represented by at least one Y 2 Substituted (C1-C6)-alkyl, H, (C1-C6)-alkoxy, (C2-C6)-alkenyl, (C2-C6)-alkynyl, -C(=O)R 6 , 3-pyridazinyl, (C2-C6)-alkenyloxy, phenoxy, benzyl, (C1-C6)-alkylsulfonyl or OH;

[0031] R 8 is H, (C1-C6)-alkyl, or (C1-C6)-alkoxy;

[0032] R 7 and R 8 Together with the nitrogen to which they are bound, they may form a fully saturated 4- to 6-membered ring, which may be substituted by at least one halogen, and the carbon atoms constituting the ring may be replaced by heteroatoms;

[0033] Y 2 is (C1-C6)-alkoxy, (C1-C6)-alkylthio, (C1-C6)-alkoxycarbonyl, -(C=O)NH-(CH2)-C(=O)R 11 , halogen, or cyano;

[0034] R 9 can be represented by at least one Z 2 Substituted (C1-C6)-alkyl, or 1-imidazolyl;

[0035] Z 2 is (C1-C6)-alkoxycarbonyl;

[0036] Z 3 is halogen, (C1-C6)-alkoxy, cyano, OH, (C1-C6)-alkoxycarbonyl, (C1-C6)-alkylcarbonyloxy, (C1-C6)-alkylsulfonyloxy, or -C(═O)OH;

[0037] Z 4 is (C1-C6)-alkyl, (C1-C6)-alkoxymethyl, or (C1-C6)-alkoxycarbonyl;

[0038] R 10 is H;

[0039] R 11 is (C1-C6)-alkoxy;

[0040] m is 1, 2, 3 or 4;

[0041] The carbon-carbon bond in the dotted line portion is a single bond or a double bond, but the carbon-carbon bonds in two dotted line portions are not both double bonds.

[0042] The present invention also relates to a difluorocrotonamide compound represented by formula (I) or a salt thereof, which is a group of compounds that have not been specifically known in the past and have particularly excellent control effects on undesirable plants.

[0043] Effects of the Invention

[0044] The composition can exert an excellent control effect on undesirable plants and can be used as a herbicide. DETAILED DESCRIPTION

[0045] In compound (I), R 4 When the number of substitutions is 2 or more, R 4 can be the same or different from each other, R 11 When the number of substitutions is 2 or more, R 11 May be the same as or different from each other.

[0046] In compound (I), halogen or halogen as a substituent may be any of fluorine, chlorine, bromine and iodine. The number of halogen as a substituent may be 1 or more than 2, and when it is more than 2, each halogen atom may be the same or different from each other. In addition, the substitution position of the halogen as a substituent may be any position.

[0047] “C P -C T " means that the number of carbon atoms is P to T. "C1-C3" means that the number of carbon atoms is 1 to 3. In addition, "may be substituted" means that it has a substituent or is unsubstituted.

[0048] In compound (I), when t is 1, an alicyclic hydrocarbon group having 4 carbon atoms (C4) is formed, and when t is 2, an alicyclic hydrocarbon group having 5 carbon atoms (C5) is formed. The C4 or C5 alicyclic hydrocarbon group refers to a cyclobutyl group, a cyclopentyl group, a 2-cyclobutenyl group, a 3-cyclopentenyl group or a 4-cyclopentenyl group.

[0049] The (C1-C6)-chain hydrocarbon group refers to a (C1-C6)-alkyl group, a (C2-C6)-alkenyl group, or a (C2-C6)-alkynyl group.

[0050] For the (C1-C6)-alkyl group or the (C1-C6)-alkyl part, there can be listed straight-chain or branched-chain alkyl groups having 1 to 6 carbon atoms, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, neopentyl, or n-hexyl.

[0051] For (C2-C6)-alkenyl or (C2-C6)-alkenyl moiety, for example, vinyl, 1-propenyl, 2-propenyl, isopropenyl, 2-methyl-1-propenyl, 1-methyl-1-propenyl, 2-methyl-2-propenyl, 1-methyl-2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-hexenyl, or 2,3-dimethyl-2-butenyl, which are linear or branched alkenyl groups having at least one double bond at any position and 2 to 6 carbon atoms. In addition, when there are geometric isomers, there are no particular restrictions as long as they are within the specified carbon number range, whether they are only one of the E isomer or the Z isomer, or a mixture of the E isomer and the Z isomer in any ratio.

[0052] For the (C2-C6)-alkynyl group or the (C2-C6)-alkynyl part, for example, ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 2-methyl-3-butynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, or 5-hexynyl, etc., which are straight-chain or branched-chain alkynyl groups having at least one triple bond at any position and 2 to 6 carbon atoms.

[0053] As can be at least one Y 1 Y of the substituent of the substituted (C1-C6)-chain hydrocarbon group 1 The substitution position can be Y 1 Any position on the substituted (C1-C6)-chain hydrocarbon group. 1 When there are 2 or more, each Y 1 May be the same as or different from each other.

[0054] In the case where at least one Y 1 In the substituted (C1-C6)-chain hydrocarbon group, at least one Y 1 When substituted, it means that one or more hydrogen atoms of a straight-chain or branched C1-C6 hydrocarbon group are replaced by Y 1 Replaced by at least one Y 1When substituted, specific examples thereof are fluoromethyl, chloromethyl, bromomethyl, iodomethyl, difluoromethyl, dichloromethyl, trifluoromethyl, chlorodifluoromethyl, trichloromethyl, bromodifluoromethyl, 1-fluoroethyl, 1-chloroethyl, 1-bromoethyl, 1,1-difluoroethyl, 1,1-dichloroethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2,2-trichloroethyl, 1,1,2,2-tetrafluoroethyl, 2-chloro-1,1,2-trifluoroethyl, pentafluoroethyl, 3,3,3 -trifluoropropyl, 2,2,3,3,3-pentafluoropropyl, 1,1,2,3,3,3-hexafluoropropyl, heptafluoropropyl, 2,2,2-trifluoro-1-(trifluoromethyl)ethyl, 1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl, 2,2,3,3,4,4,4-heptafluorobutyl, nonafluorobutyl, methoxymethyl, 1-methoxyethyl, 2-methoxyethyl, 1-methoxypropyl, 2-methoxypropyl, 3-methoxypropyl, 1-methoxybutyl, 2-methoxybutyl, 3-methoxybutyl, 4-methoxybutyl, 3-methoxy- 1-methylpropyl, 3-methoxy-2-methylpropyl, 2-methoxy-1,1-dimethylethyl, 5-methoxypentyl, 4-methoxy-1-methylbutyl, 6-methoxyhexyl, ethoxymethyl, 2-ethoxyethyl, 3-ethoxypropyl, 4-ethoxybutyl, 5-ethoxypentyl, 6-ethoxyhexyl, n-propoxymethyl, 2-n-propoxyethyl, 3-n-propoxypropyl, 4-n-propoxybutyl, 5-n-propoxypentyl, 6-n-propoxyhexyl, n-butoxymethyl, 2-n-butoxyethyl, 3-n-butoxypropyl, 4-n-butoxy The following examples are also contemplated: 1-butyl, 5-n-butoxypentyl, 6-n-butoxyhexyl, n-pentyloxymethyl, 2-n-pentyloxyethyl, 3-n-pentyloxypropyl, 4-n-pentyloxybutyl, 5-n-pentyloxypentyl, 6-n-pentyloxyhexyl, n-hexyloxymethyl, 2-n-hexyloxyethyl, 3-n-hexyloxypropyl, 4-n-hexyloxybutyl, 5-n-hexyloxypentyl, 6-n-hexyloxyhexyl, cyanomethyl, dicyanomethyl, 1-cyanoethyl, 2-cyanoethyl, 3-cyanopropyl, 4-cyanobutyl, 5-cyanopentyl, or 6-cyanohexyl, etc. are contemplated: 1 A partially or completely substituted linear or branched alkyl group having 1 to 6 carbon atoms.

[0055] In addition, for example, 1-chlorovinyl, 2-chlorovinyl, 2-fluorovinyl, 2,2-dichlorovinyl, 2,2-difluorovinyl, 3-chloro-2-propenyl, 3-fluoro-2-propenyl, 2-chloro-2-propenyl, or 4-chloro-3-butenyl, etc. may be replaced by one or more identical or different Y 1A linear or branched alkenyl group having 2 to 6 carbon atoms which is partially or completely substituted. In addition, examples thereof include 2-chloroethynyl, 2-bromoethynyl, 2-iodoethynyl, 3-chloro-2-propynyl or 4-chloro-2-butynyl, which are replaced by one or more identical or different Y 1 A partially or completely substituted straight-chain or branched-chain alkynyl group having 2 to 6 carbon atoms.

[0056] As can be at least one Z 3 The substituent Z of the substituted (C1-C6)-chain hydrocarbon group 3 The substitution position can be Z 3 Any position on the substituted (C1-C6)-chain hydrocarbon group. 3 When there are 2 or more, each Z 3 May be the same as or different from each other.

[0057] As can be at least one Z 1 The substituent Z of the substituted (C1-C6)-alkyl group 1 The substitution position can be Z 1 Any position on the substituted (C1-C6)-alkyl group. 1 When there are 2 or more, each Z 1 May be the same as or different from each other.

[0058] As can be at least one Z 2 The substituent Z of the substituted (C1-C6)-alkyl group 2 The substitution position can be Z 2 Any position on the substituted (C1-C6)-alkyl group. 2 When there are 2 or more, each Z 2 May be the same as or different from each other.

[0059] For the (C1-C6)-alkyl group which may be substituted with at least one halogen, when substituted, it means that one or more hydrogen atoms of the straight-chain or branched-chain C1-C6 hydrocarbon group are replaced by halogen atoms. Specifically, for example, fluoromethyl, chloromethyl, bromomethyl, iodomethyl, difluoromethyl, dichloromethyl, trifluoromethyl, chlorodifluoromethyl, trichloromethyl, bromodifluoromethyl, 1-fluoroethyl, 1-chloroethyl, 1-bromoethyl, 1,1-difluoroethyl, 1,1-dichloroethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2,2-trichloroethyl, 1,1,2,2-tetrafluoroethyl, 2-chloro- A linear or branched alkyl group having 1 to 6 carbon atoms which is partially or completely substituted with one or more identical or different halogens, such as a 1,1,2-trifluoroethyl group, a pentafluoroethyl group, a 3,3,3-trifluoropropyl group, a 2,2,3,3,3-pentafluoropropyl group, a 1,1,2,3,3,3-hexafluoropropyl group, a heptafluoropropyl group, a 2,2,2-trifluoro-1-(trifluoromethyl)ethyl group, a 1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl group, a 2,2,3,3,4,4,4-heptafluorobutyl group, or a nonafluorobutyl group.

[0060] As can be at least one Y 2 The substituent Y of the substituted (C1-C6)-alkyl group 2 The substitution position can be Y 2 Any position on the substituted (C1-C6)-alkyl group. 2 When there are 2 or more, each Y 2 May be the same as or different from each other.

[0061] For the (C1-C6)-alkoxy or (C1-C6)-alkoxy part, examples include methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, tert-butoxy, n-pentoxy, isopentoxy, or n-hexyloxy, which are straight-chain or branched-chain alkoxy groups having 1 to 6 carbon atoms.

[0062] For (C1-C6)-alkoxy which may be substituted with at least one halogen, when substituted, it means that one or more hydrogen atoms of the linear or branched C1-C6 alkoxy group are replaced by a halogen atom. For example, a linear or branched alkoxy group having 2 to 6 carbon atoms and partially or completely substituted with one or more identical or different halogen atoms, such as a fluoromethoxy group, a difluoromethoxy group, a trifluoromethoxy group, a chlorodifluoromethoxy group, a bromodifluoromethoxy group, a dichlorofluoromethoxy group, a chloromethoxy group, a dichloromethoxy group, a trichloromethoxy group, a bromomethoxy group, a 1-fluoroethoxy group, a 2-fluoroethoxy group, a 2-chloroethoxy group, a 2-bromoethoxy group, a 2,2-difluoroethoxy group, a 2,2,2-trifluoroethoxy group, a 1,1,2,2-tetrafluoroethoxy group, a pentafluoroethoxy group, a 2,2,2-trichloroethoxy group, a 1-fluoropropoxy group, a 2-fluoropropoxy group, a 3-fluoropropoxy group, a 3-chloropropoxy group, a 3-bromopropoxy group, a 1-fluorobutoxy group, a 2-fluorobutoxy group, a 3-fluorobutoxy group, a 4-fluorobutoxy group, or a 4-chlorobutoxy group can be mentioned.

[0063] As for the (C2-C6)-alkenyloxy moiety, for example, a linear or branched alkenyloxy group having 2 to 6 carbon atoms such as vinyloxy, 1-propenyloxy, 2-propenyloxy, isopropenyloxy, 2-methyl-1-propenyloxy, 1-methyl-1-propenyloxy, 2-methyl-2-propenyloxy, 1-methyl-2-propenyloxy, 1-butenyloxy, 2-butenyloxy, 3-butenyloxy, 1-pentenyloxy, 2-pentenyloxy, 2-methyl-2-butenyloxy, 3-methyl-2-butenyloxy, 1-hexenyloxy, or 2,3-dimethyl-2-butenyloxy can be mentioned. In addition, when there are geometric isomers, there is no particular limitation as long as the carbon number is within the specified range, and only one of the E isomer and the Z isomer is present, or a mixture of the E isomer and the Z isomer in any ratio.

[0064] As for the (C1-C6)-alkylthio part, for example, a straight-chain or branched-chain alkylthio group having 1 to 6 carbon atoms such as methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, sec-butylthio, tert-butylthio, n-pentylthio, isopentylthio or n-hexylthio can be mentioned.

[0065] As for the (C1-C6)-alkylsulfonyl moiety, there can be mentioned a straight-chain or branched-chain alkylsulfonyl group having 1 to 6 carbon atoms, such as methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, isopropylsulfonyl, n-butylsulfonyl, sec-butylsulfonyl, n-pentylsulfonyl, isopentylsulfonyl or n-hexylsulfonyl.

[0066] As for the (C1-C6)-alkylsulfonyloxy part, there can be mentioned a straight-chain or branched-chain (C1-C6)-alkylsulfonyloxy group having 1 to 6 carbon atoms, such as methylsulfonyloxy, ethylsulfonyloxy, n-propylsulfonyloxy, isopropylsulfonyloxy, n-butylsulfonyloxy, sec-butylsulfonyloxy, n-pentylsulfonyloxy, isopentylsulfonyloxy or n-hexylsulfonyloxy.

[0067] For the (C1-C6)-alkoxycarbonyl part, examples include methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, isopropoxycarbonyl, n-butoxycarbonyl, sec-butoxycarbonyl, n-pentoxycarbonyl, isopentyloxycarbonyl, or n-hexyloxycarbonyl, which are straight-chain or branched alkoxycarbonyl groups having 1 to 6 carbon atoms.

[0068] For the (C1-C6)-alkylcarbonyloxy part, there can be mentioned straight-chain or branched-chain alkylcarbonyloxy groups having 1 to 6 carbon atoms, such as methylcarbonyloxy, ethylcarbonyloxy, n-propylcarbonyloxy, isopropylcarbonyloxy, n-butylcarbonyloxy, sec-butylcarbonyloxy, tert-butylcarbonyloxy, n-pentylcarbonyloxy, isopentylcarbonyloxy, or n-hexylcarbonyloxy.

[0069] As the (C3-C6)-cycloalkyl moiety, there may be mentioned cycloalkyl groups having 3 to 6 carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.

[0070] Can be at least one Z 4 Substituted 2-imidazolyl means substituted with 1, 2 or 3 Z 4 substituted 2-imidazolyl or unsubstituted 2-imidazolyl. 4 The substitution position can be Z 4 Any position on the substituted 2-imidazolyl group. 4 When there are 2 or 3, each Z 4 May be the same as or different from each other.

[0071] The 4- to 6-membered oxygen-containing saturated heterocyclic ring refers to a 4- to 6-membered saturated heterocyclic ring containing 1 to 2 heteroatoms, wherein the heteroatoms are oxygen atoms. Specifically, 3-oxetanyl, 2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 1,3-dioxolan-4-yl, 2-tetrahydropyranyl, 3-tetrahydropyranyl, 4-tetrahydropyranyl, 1,3-dioxane-4-yl, 1,3-dioxane-5-yl and the like can be mentioned.

[0072] The pyridyl group refers to a 2-pyridyl group, a 3-pyridyl group or a 4-pyridyl group.

[0073] In compound (I), R 4 "-C(=O)NR 7 R 8”, R 7 and R 8 They can also form a fully saturated 4- to 6-membered ring together with the nitrogen to which they are bonded. The ring can be substituted with at least one halogen. In addition, the carbon atoms constituting the ring can also be replaced with heteroatoms. As the above-mentioned heteroatoms, O, S, S(=O), S(=O)2 and N can be listed. The number of heteroatoms contained in the ring is usually one. 7 R 8 When " forms a ring, specific examples thereof include formula (a-1) to formula (a-14). In addition, # represents a bonding position.

[0074] Formula (a-1) to Formula (a-14):

[0075]

[0076] In the formula, ma is 0, 1, 2 or 3, and Hal is a halogen.

[0077] The carbon-carbon bond of the dotted line portion in formula (I) (hereinafter, also referred to as the dotted line portion):

[0078]

[0079] However, the two dotted lines are not double bonds at the same time.

[0080] In formula (I), when t is 1 and both of the two dotted line portions are single bonds, this represents a compound represented by formula (IAa) or a salt thereof (hereinafter also referred to as compound (IAa)).

[0081]

[0082] In the formula, R 1 , R 2 , R 3 , R 4 and m are the same as those defined in formula (I). It should be noted that in compound (IAa), R 4 When the number of substitutions is 2 or more, R 4 May be the same as or different from each other.

[0083] In formula (I), when t is 1, one of the two dotted line portions is a double bond and the other is a single bond, this represents a compound represented by formula (IAb) or a salt thereof (hereinafter also referred to as compound (IAb)).

[0084]

[0085] In the formula, R 1 , R 2 , R 3 , R4 and m are the same as those defined in formula (I). It should be noted that in compound (IAb), R 4 When the number of substitutions is 2 or more, R 4 May be the same as or different from each other.

[0086] In formula (I), when t is 2 and both dotted line portions are single bonds, this represents a compound represented by formula (IBa) or a salt thereof (hereinafter also referred to as compound (IBa)).

[0087]

[0088] In the formula, R 1 , R 2 , R 3 , R 4 and m are the same as those defined in formula (I). It should be noted that in compound (IBa), R 4 When the number of substitutions is 2 or more, R 4 May be the same as or different from each other.

[0089] In formula (I), when t is 2, one of the two dotted parts is a double bond and the other is a single bond, it represents a compound represented by formula (IBb) or formula (IBc), or a salt thereof (hereinafter, the compound represented by formula (IBb) is also referred to as compound (IBb), and the compound represented by formula (IBc) is also referred to as compound (IBc)).

[0090]

[0091] In the formula, R 1 , R 2 , R 3 , R 4 and m are the same as those defined in formula (I). It should be noted that in compound (IBb) or compound (IBc), R 4 When the number of substitutions is 2 or more, R 4 May be the same as or different from each other.

[0092] Therefore, compound (I) includes the above-mentioned compounds (IAa), (IAb), (IBa), (IBb) and (IBc). In addition, the description of compound (I) in this specification includes the description of the above-mentioned compounds (IAa), (IAb), (IBa), (IBb) and (IBc). It should be noted that the symbols in the above-mentioned compounds (IAa), (IAb), (IBa), (IBb) and (IBc) have the same meanings as the symbols in compound (I).

[0093] In the present invention, the compound wherein t is 1 or 2 and both dotted line parts are represented by single bonds in formula (I) is preferred, and the compound wherein t is 2 and one of the two dotted line parts is a single bond and the other is represented by a double bond in formula (I) is preferred. That is, in the present invention, the above-mentioned compounds (IAa), (IBa), (IBb), or (IBc) are preferred.

[0094] The salt of compound (I) includes all salts as long as they are agriculturally acceptable salts, for example, alkali metal salts (for example, sodium salts, potassium salts, etc.), alkaline earth metal salts (for example, calcium salts, magnesium salts, etc.), amine salts (for example, dimethylamine salts, triethylamine salts, etc.), inorganic acid salts (for example, hydrochlorides, perchlorates, sulfates, nitrates, etc.), organic acid salts (for example, acetates, methanesulfonates, etc.), etc.

[0095] Compound (I) has various isomers, such as optical isomers, geometric isomers, etc., but the present invention includes both individual isomers and isomer mixtures. It should be noted that in compound (I), various isomers other than the above-mentioned isomers are also included within the scope of technical common sense in the technical field. Moreover, various isomers can be prepared respectively using technical common sense and general experimental methods in the technical field.

[0096] In addition, depending on the type of isomer, the chemical structure may be different from the described structural formula, but those skilled in the art will fully recognize that they are in an isomer relationship, and therefore, it is obvious that they are within the scope of the present invention.

[0097] Next, the method for producing compound (I) is described.

[0098] For compound (I), it can be manufactured according to the manufacturing method A (reaction A to reaction Z and reaction AA to reaction AC) shown below, and the manufacturing method of the common salt, but the method for obtaining the compound is not limited to these methods. For example, for compound (I) of the present invention, it can also be manufactured by applying various substituent conversion reactions known in the art (such as alkylation reaction, haloalkylation reaction, cross-coupling reaction such as Suzuki coupling reaction, Sandmeyer type reaction, halogenation reaction, oxidation reaction, reduction reaction, etc.) to the substituent on the phenyl group. In addition, as required, in the manufacture of the compound of the present invention, the protection and deprotection reactions commonly used in the art can be applied. When implementing the reaction, it can be carried out under an inert gas atmosphere such as nitrogen and argon if necessary, and a salt reagent can also be used.

[0099] Manufacturing Method A

[0100] [Reaction A]

[0101] Reaction A is a method of reacting a compound of formula (II) with a compound of formula (X-1) to obtain a compound of formula (I).

[0102]

[0103] Where V 1 is OH, a chlorine atom or a bromine atom, and other symbols are as described above.

[0104] Reaction A can usually be carried out in the presence of a base and a solvent by adding a dehydration condensation agent as needed. It should be noted that when using a specific dehydration condensation agent such as a carbodiimide condensation agent, an imidazole condensation agent or a triazine condensation agent, the reaction proceeds even in the absence of a base. Relative to 1 equivalent of the compound of formula (II), the compound of formula (X-1) can be used in 0.5 to 10 equivalents, preferably 1 to 5 equivalents (equivalent is molar equivalent, the same below).

[0105] As for the base, one or more of them can be appropriately selected from carbonates such as sodium carbonate and potassium carbonate; bicarbonates such as sodium bicarbonate and potassium bicarbonate; metal hydroxides such as sodium hydroxide and potassium hydroxide; metal hydrides such as sodium hydride and potassium hydride; amines such as triethylamine and N,N-diisopropylethylamine; pyridines such as pyridine, 4-dimethylaminopyridine and 2,6-lutidine; alkali metal carboxylates such as sodium acetate and potassium acetate, etc., or mixed and used. 0.5 to 10 equivalents, preferably 1 to 5 equivalents of the base can be used relative to 1 equivalent of the compound of formula (II).

[0106] The solvent may be any solvent as long as it is inert to the reaction, and may be selected from, for example, aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; aliphatic hydrocarbons such as carbon tetrachloride, chloroform, dichloromethane, dichloroethane, trichloroethane, hexane, and cyclohexane; ethers such as dioxane, tetrahydrofuran, diethyl ether, and dimethoxyethane; esters such as methyl acetate and ethyl acetate; aprotic polar solvents such as dimethyl sulfoxide, cyclopentane, N,N-dimethylacetamide, N,N-dimethylformamide, N-methylpyrrolidone, pyridine, acetonitrile, and propionitrile; ketones such as acetone and methyl ethyl ketone; protic polar solvents such as methanol and ethanol; water, etc., at least one or more of them may be appropriately selected.

[0107] As the dehydration condensation agent, a carbodiimide condensation agent such as N,N'-dicyclohexylcarbodiimide (DCC), 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide (EDC) or its hydrochloride; an imidazole condensation agent such as 1,1'-carbonyldiimidazole (CDI); a triazine condensation agent such as 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (DMT-MM); a 1H-benzotriazol-1-yloxytripyrrolidinophosphonium hexafluorophosphate (P Phosphonium condensation agents such as phosphonium condensation agents such as 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate (HATU); acid anhydrides such as 2-methyl-6-nitrobenzoic anhydride (MNBA); 2-halogenopyridinium salts such as 2-chloro-1-methylpyridinium p-toluenesulfonate; propylphosphonic anhydride (cyclic trimer) (T3P); diphenylphosphoryl azide (DPPA), etc., are appropriately selected to be used in combination. If necessary, conventional additives such as 1-hydroxybenzotriazole (HOBt) and 4-N,N-dimethylaminopyridine (DMAP) used together with the dehydration condensation agent can be added. When an additive is used in reaction A, one or more of the additives can be appropriately selected to be used in combination. The dehydration condensation agent can be used in an amount of 0.5 to 10 equivalents, preferably 1 to 5 equivalents, based on 1 equivalent of the compound of formula (II). The additive can be used in an amount of 0.1 to 10 equivalents, preferably 1 to 5 equivalents, based on 1 equivalent of the compound of formula (II).

[0108] The reaction temperature of reaction A is about -30°C to 80°C, preferably about -10°C to 50°C, and the reaction time is usually about 10 minutes to 30 hours, preferably about 30 minutes to 15 hours. It should be noted that when a dehydration condensation agent is used in reaction A, the reaction temperature is about -30°C to 120°C, preferably about 0°C to 80°C, and the reaction time is usually about 10 minutes to 100 hours, preferably about 30 minutes to 30 hours.

[0109] The compound of formula (II) used in reaction A can be produced by the following reaction 1-5, reaction 1-6 or a known method. A commercially available compound of formula (X-1) can be used.

[0110] [Reaction B] and [Reaction C]

[0111] Reaction B is a method of hydrolyzing the compound of formula (I-1) to obtain the compound of formula (I-2). Reaction C is a method of reacting the compound of formula (I-2) with the compound of formula (X-2) to obtain the compound of formula (I-3).

[0112]

[0113] In the formula, A is -O-, -S-, or -NR 8 -, L 1 is a (C1-C6)-chain hydrocarbon group, n is 0, 1, 2 or 3 (n is 0 means there is no R 4 When A is -O-, B is substituted by at least one Z 1 substituted (C1-C6)-alkyl, H, (C3-C6)-cycloalkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, or a 4- to 6-membered oxygen-containing saturated heterocycle. When A is -S-, B is a (C1-C6)-alkyl, (C3-C6)-cycloalkyl, or benzyl group which may be substituted with at least one halogen. When A is -NR 8 -, B can be 2 Substituted (C1-C6)-alkyl, H, (C1-C6)-alkoxy, (C2-C6)-alkenyl, (C2-C6)-alkynyl, -C(=O)R 6 , 3-pyridazinyl, (C2-C6)-alkenyloxy, phenoxy, benzyl, (C1-C6)-alkylsulfonyl or OH. It should be noted that when A is -NR 8 -, B and R 8 They may also form a fully saturated 4- to 6-membered ring together with the nitrogen to which they are bonded, and the ring may be substituted with at least one halogen. In addition, the carbon atoms constituting the ring may also be replaced with heteroatoms. Other symbols are as described above.

[0114] Reaction B can usually be carried out by mixing the compound of formula (I-1) with a base or an acid in the presence of a solvent.

[0115] For the base, for example, alkali metal hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide; alkali metal carbonates such as sodium carbonate, potassium carbonate, cesium carbonate; alkali metal bicarbonates such as sodium bicarbonate and potassium bicarbonate; alkaline earth metal carbonates such as calcium carbonate and barium carbonate; alkaline earth metal hydroxides such as calcium hydroxide and barium hydroxide, etc. can be listed, but are not limited to these. As the base, one or more of these bases can be appropriately selected and used in combination. Relative to 1 equivalent of the compound of formula (I-1), 1 to 10 equivalents, preferably 1 to 5 equivalents of the base can be used.

[0116] As for the acid, for example, organic acids such as formic acid, acetic acid, methanesulfonic acid, p-toluenesulfonic acid, trifluoroacetic acid, trifluoromethanesulfonic acid, and inorganic acids such as hydrochloric acid, sulfuric acid, and hydrogen bromide can be cited, but are not limited to these. As the acid, one or more of these acids can be appropriately selected and used in combination. Relative to 1 equivalent of the compound of formula (I-1), 0.1 to 30 equivalents, preferably 1 to 10 equivalents of the acid can be used.

[0117] The solvent may be any solvent as long as it is inert to the reaction, for example, one or more solvents may be appropriately selected from aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; aliphatic hydrocarbons such as hexane and cyclohexane; ethers such as dioxane, tetrahydrofuran, diethyl ether, and dimethoxyethane; non-protonic polar solvents such as acetonitrile, N,N-dimethylformamide, dimethyl sulfoxide, N,N-dimethylacetamide, hexamethylphosphoric acid triamide, and cyclopentane sulfone; protonic polar solvents such as methanol, ethanol, and isopropanol; water, etc.

[0118] When a base is used in reaction B, the reaction temperature is about -30°C to 120°C, preferably about -10°C to 80°C, and the reaction time is usually about 10 minutes to 30 hours, preferably about 30 minutes to 15 hours. When an acid is used in reaction B, the reaction temperature of reaction B is about -30°C to 200°C, preferably about 0°C to 100°C, and the reaction time is usually about 10 minutes to 30 hours, preferably about 30 minutes to 15 hours.

[0119] The compound of formula (I-1) used in reaction B can be produced according to the above reaction A or a known method.

[0120] Reaction C can be carried out according to the above reaction A. For the compound of formula (X-2), 0.5 to 10 equivalents can be used relative to 1 equivalent of the compound of formula (I-2), preferably 1 to 5 equivalents. For the base, 0.5 to 10 equivalents can be used relative to 1 equivalent of the compound of formula (I-2), preferably 1 to 5 equivalents. For the dehydration condensation agent, 0.5 to 10 equivalents can be used relative to 1 equivalent of the compound of formula (I-2), preferably 1 to 5 equivalents. For the additive, 0.1 to 10 equivalents can be used relative to 1 equivalent of the compound of formula (I-2), preferably 1 to 5 equivalents.

[0121] As the compound of formula (X-2) used in Reaction C, a commercially available product can be used.

[0122] [Reaction D]

[0123] Reaction D is a method of reacting a compound of formula (I-1) with a compound of formula (X-3) to obtain a compound of formula (I-4).

[0124]

[0125] Where, L 2 is (C1-C6)-alkyl. Other symbols are as described above.

[0126] Reaction D can usually be carried out by mixing the compound of formula (I-1) with the compound of formula (X-3) in the presence of a solvent and a base. The compound of formula (X-3) can be used in an amount of 0.5 to 10 equivalents, preferably 1 to 5 equivalents, relative to 1 equivalent of the compound of formula (I-1).

[0127] As the base, one or more of metal amine salts such as lithium diisopropylamide and lithium bis(trimethylsilyl)amide; metal hydrides such as sodium hydride and potassium hydride; metal alkoxides such as potassium tert-butoxide and lithium tert-butoxide can be appropriately selected and used in combination. The base can be used in an amount of 1 to 10 equivalents, preferably 1 to 5 equivalents, relative to 1 equivalent of the compound of formula (I-1).

[0128] The solvent may be any solvent as long as it is inert to the reaction. For example, one or more solvents may be appropriately selected from aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; aliphatic hydrocarbons such as hexane and cyclohexane; and ethers such as dioxane, tetrahydrofuran, diethyl ether, and dimethoxyethane.

[0129] The reaction temperature of Reaction D is about -100°C to 100°C, preferably about -80°C to 50°C, and the reaction time is usually about 10 minutes to 30 hours, preferably about 1 hour to 15 hours.

[0130] The compound of formula (I-1) used in reaction D can be produced according to the above reaction A or a known method. A commercially available product can be used as the compound of formula (X-3).

[0131] [Reaction E]

[0132] Reaction E is a method of reacting a compound of formula (I-3-1) with an alkylating agent to obtain a compound of formula (I-5).

[0133]

[0134] Wherein, the symbols are as described above.

[0135] Reaction E can usually be carried out by mixing the compound of formula (I-3-1) and an alkylating agent in the presence of a solvent.

[0136] Examples of the alkylating agent include, but are not limited to, metal alkyl salts such as methyllithium and n-butyllithium. The alkylating agent can be used in an amount of 0.5 to 10 equivalents, preferably 1 to 5 equivalents, relative to 1 equivalent of the compound of formula (I-3-1).

[0137] The solvent may be any solvent as long as it is inert to the reaction. For example, one or more solvents may be appropriately selected from aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; aliphatic hydrocarbons such as hexane and cyclohexane; and ethers such as dioxane, tetrahydrofuran, diethyl ether, and dimethoxyethane.

[0138] The reaction temperature of Reaction E is about -100°C to 100°C, preferably about -80°C to 50°C, and the reaction time is usually about 10 minutes to 30 hours, preferably about 1 hour to 15 hours.

[0139] The compound of formula (I-3-1) used in Reaction E can be produced according to the above-mentioned Reaction C or a known method.

[0140] [Reaction F]

[0141] Reaction F is a method of reacting a compound of formula (I-2), diphenylphosphoryl azide (DPPA) and a compound of formula (X-4) to obtain a compound of formula (I-6).

[0142]

[0143] The symbols in the formula are as described above.

[0144] Reaction F can usually be carried out by mixing the compound of formula (I-2), DPPA and the compound of formula (X-4) in the presence of a solvent and a base. DPPA can be used in an amount of 0.5 to 10 equivalents, preferably 1 to 5 equivalents, relative to 1 equivalent of the compound of formula (I-2). 1 to 100 equivalents, preferably 1 to 30 equivalents, of the compound of formula (X-4) can be used relative to 1 equivalent of the compound of formula (I-2).

[0145] For the base, for example, one or more of carbonates such as sodium carbonate and potassium carbonate; bicarbonates such as sodium bicarbonate and potassium bicarbonate; metal hydroxides such as sodium hydroxide and potassium hydroxide; metal hydrides such as sodium hydride and potassium hydride; amines such as triethylamine and N,N-diisopropylethylamine; pyridines such as pyridine, 4-dimethylaminopyridine and 2,6-lutidine; alkali metal carboxylates such as sodium acetate and potassium acetate can be appropriately selected and used in combination. The base can be used in an amount of 1 to 30 equivalents, preferably 1 to 10 equivalents, relative to 1 equivalent of the compound of formula (I-2).

[0146] The solvent may be any solvent as long as it is inert to the reaction, for example, one or more solvents may be appropriately selected from aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; aliphatic hydrocarbons such as hexane and cyclohexane; ethers such as dioxane, tetrahydrofuran, diethyl ether, and dimethoxyethane; esters such as methyl acetate and ethyl acetate; and aprotic polar solvents such as dimethyl sulfoxide, cyclopentane, N,N-dimethylacetamide, N,N-dimethylformamide, N-methylpyrrolidone, pyridine, acetonitrile, and propionitrile.

[0147] The reaction temperature of Reaction F is about -30°C to 180°C, preferably about 30°C to 130°C, and the reaction time is usually about 10 minutes to 30 hours, preferably about 30 minutes to 15 hours.

[0148] The compound of formula (I-2) used in reaction F can be produced according to the above reaction B or a known method. A commercially available product can be used as the compound of formula (X-4).

[0149] [Reaction G]

[0150] Reaction G is a method of reacting a compound of formula (I-1) with a reducing agent to obtain a compound of formula (I-7).

[0151]

[0152] The symbols in the formula are as described above.

[0153] Reaction G can usually be carried out by mixing the compound of formula (I-1) with a reducing agent in the presence of a solvent.

[0154] As the reducing agent, metal hydrides such as lithium borohydride, sodium borohydride, lithium aluminum hydride, and diisobutylaluminum hydride can be cited, but are not limited thereto. 0.5 to 10 equivalents, preferably 1 to 5 equivalents of the reducing agent can be used per 1 equivalent of the compound of formula (I-1).

[0155] The solvent may be any solvent as long as it is inert to the reaction, for example, one or more solvents may be appropriately selected from aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; aliphatic hydrocarbons such as hexane and cyclohexane; ethers such as dioxane, tetrahydrofuran, diethyl ether, and dimethoxyethane; protic polar solvents such as methanol and ethanol; water, etc.

[0156] The reaction temperature of Reaction G is about -100°C to 100°C, preferably about -80°C to 50°C, and the reaction time is usually about 10 minutes to 30 hours, preferably about 1 hour to 15 hours.

[0157] The compound of formula (I-1) used in reaction G can be produced according to the above reaction A or a known method.

[0158] [Reaction H], [Reaction I], and [Reaction J]

[0159] Reaction H is a method for reacting a compound of formula (I-7) with a compound of formula (X-5) to obtain a compound of formula (I-8). Reaction I is a method for reacting a compound of formula (I-7) with a halogenating agent to obtain a compound of formula (I-9). Reaction J is a method for reacting a compound of formula (I-9) with a cyaniding agent to obtain a compound of formula (I-10).

[0160]

[0161] In the formula, U is (C1-C6)-alkylcarbonyl or (C1-C6)-alkylsulfonyl, and X is each atom of fluorine, chlorine, bromine or iodine. Other symbols are as described above.

[0162] Reaction H can be generally carried out by reacting a compound of formula (I-7) with a compound of formula (X-5) in the presence of a solvent and a base. The compound of formula (X-5) can be used in an amount of 0.5 to 10 equivalents, preferably 1 to 5 equivalents, relative to 1 equivalent of the compound of formula (I-7).

[0163] For the base, for example, one or more of carbonates such as sodium carbonate and potassium carbonate; bicarbonates such as sodium bicarbonate and potassium bicarbonate; metal hydroxides such as sodium hydroxide and potassium hydroxide; metal hydrides such as sodium hydride and potassium hydride; amines such as triethylamine and N,N-diisopropylethylamine; pyridines such as pyridine, 4-dimethylaminopyridine and 2,6-lutidine; alkali metal carboxylates such as sodium acetate and potassium acetate can be appropriately selected and used in combination. The base can be used in an amount of 0.5 to 10 equivalents, preferably 1 to 5 equivalents, relative to 1 equivalent of the compound of formula (I-7).

[0164] The solvent may be any solvent as long as it is inert to the reaction, for example, one or more solvents may be appropriately selected from aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; aliphatic hydrocarbons such as carbon tetrachloride, chloroform, dichloromethane, dichloroethane, trichloroethane, hexane, and cyclohexane; ethers such as dioxane, tetrahydrofuran, diethyl ether, and dimethoxyethane; esters such as methyl acetate and ethyl acetate; aprotic polar solvents such as dimethyl sulfoxide, cyclopentane, N,N-dimethylacetamide, N,N-dimethylformamide, N-methylpyrrolidone, pyridine, acetonitrile, and propionitrile; ketones such as acetone and methyl ethyl ketone; protic polar solvents such as methanol and ethanol; water, etc.

[0165] The reaction temperature of Reaction H is about -30°C to 120°C, preferably about 0°C to 80°C, and the reaction time is usually about 10 minutes to 30 hours, preferably about 30 minutes to 15 hours.

[0166] Reaction I can generally be carried out by mixing a compound represented by the following formula (I-7) and a halogenating agent in the presence of a solvent and, if necessary, a base.

[0167] For the halogenating agent, for example, one or more of metal fluorides such as potassium fluoride and cesium fluoride; phosphorus halides such as phosphorus trichloride and phosphorus tribromide; halogen molecules such as bromine and iodine; carbon tetrahalides such as carbon tetrachloride and carbon tetrabromide can be appropriately selected and used in combination. For 1 equivalent of the compound of formula (I-7), 0.5 to 10 equivalents, preferably 1 to 5 equivalents of the halogenating agent can be used. In addition, when carbon tetrahalide is used as the halogenating agent, triphenylphosphine is used as an additive (Appel reaction). When triphenylphosphine is used, 0.5 to 10 equivalents, preferably 1 to 5 equivalents, of triphenylphosphine can be used for 1 equivalent of the compound of formula (I-7).

[0168] For the base, for example, one or more kinds can be appropriately selected from carbonates such as sodium carbonate and potassium carbonate; bicarbonates such as sodium bicarbonate and potassium bicarbonate; metal hydroxides such as sodium hydroxide and potassium hydroxide; metal hydrides such as sodium hydride and potassium hydride; amines such as triethylamine and N,N-diisopropylethylamine; pyridines such as pyridine, 4-dimethylaminopyridine and 2,6-lutidine; alkali metal carboxylates such as sodium acetate and potassium acetate, etc. 0.1 to 10 equivalents, preferably 1 to 5 equivalents of the base can be used relative to 1 equivalent of the compound of formula (I-7).

[0169] The solvent may be any solvent as long as it is inert to the reaction, for example, one or more solvents may be appropriately selected from aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; aliphatic hydrocarbons such as carbon tetrachloride, chloroform, dichloromethane, dichloroethane, trichloroethane, hexane, and cyclohexane; ethers such as dioxane, tetrahydrofuran, diethyl ether, and dimethoxyethane; esters such as methyl acetate and ethyl acetate; aprotic polar solvents such as dimethyl sulfoxide, sulfolane, N,N-dimethylacetamide, N,N-dimethylformamide, N-methylpyrrolidone, pyridine, acetonitrile, and propionitrile; and ketones such as acetone and methyl ethyl ketone.

[0170] The reaction temperature of Reaction I is about -30°C to 150°C, preferably about 0°C to 100°C, and the reaction time is usually about 10 minutes to 30 hours, preferably about 30 minutes to 15 hours.

[0171] The compound of formula (I-7) used in reaction H and reaction I can be produced according to the above reaction G or a known method. The compound of formula (X-5) used in reaction H can be a commercially available product.

[0172] Reaction J can generally be carried out by mixing the compound of formula (I-9) with a cyaniding agent in the presence of a solvent.

[0173] The cyaniding agent can be selected from metal cyanides such as sodium cyanide and potassium cyanide, or two or more can be mixed and used. 0.5 to 10 equivalents, preferably 1 to 5 equivalents of the cyaniding agent can be used per 1 equivalent of the compound of formula (I-9).

[0174] The solvent may be any solvent as long as it is inert to the reaction, for example, one or more solvents may be appropriately selected from aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; aliphatic hydrocarbons such as carbon tetrachloride, chloroform, dichloromethane, dichloroethane, trichloroethane, hexane, and cyclohexane; ethers such as dioxane, tetrahydrofuran, diethyl ether, and dimethoxyethane; and non-protonic polar solvents such as dimethyl sulfoxide, cyclopentane, N,N-dimethylacetamide, N,N-dimethylformamide, N-methylpyrrolidone, pyridine, acetonitrile, and propionitrile.

[0175] The reaction temperature of Reaction J is about -30°C to 120°C, preferably about 0°C to 80°C, and the reaction time is usually about 10 minutes to 30 hours, preferably about 30 minutes to 15 hours.

[0176] [Reaction K] and [Reaction L]

[0177] Reaction K is a method for reacting a compound of formula (I-7) with an oxidizing agent to obtain a compound of formula (I-11). Reaction L is a Horner-Wadsworth-Emmons reaction, which is a method for reacting a compound of formula (I-11) with a compound of formula (X-6) to obtain a compound of formula (I-12).

[0178]

[0179] In the formula, Alk is a (C1-C6)-alkyl group. Other symbols are as described above.

[0180] Reaction K can usually be carried out by mixing the compound of formula (I-7) and an oxidizing agent in the presence of a solvent.

[0181] As the oxidant, there is no particular limitation as long as the reaction can proceed, and examples thereof include hypervalent iodine compounds such as Dess-Martin Periodinane used in Dess-Martin oxidation; metal oxides such as manganese dioxide; sulfur oxides such as sulfur trioxide pyridine complex; dimethyl sulfoxide (DMSO) used in Swern oxidation reaction, etc. Relative to 1 equivalent of the compound of formula (I-7), 0.5 to 30 equivalents, preferably 1 to 10 equivalents of the oxidant can be used. It should be noted that in the case of the Swern oxidation reaction, oxalyl chloride and acetic anhydride are added as activators. Relative to 1 equivalent of the compound of formula (I-7), these activators can be used in 0.5 to 10 equivalents, preferably 1 to 5 equivalents.

[0182] The solvent may be any solvent as long as it is inert to the reaction. For example, one or two solvents may be appropriately selected from aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; aliphatic hydrocarbons such as hexane and cyclohexane; and ethers such as dioxane, tetrahydrofuran, diethyl ether, and dimethoxyethane.

[0183] The reaction temperature of reaction K is about -80°C to 100°C, preferably about 0°C to 50°C, and the reaction time is usually about 10 minutes to 30 hours, preferably about 1 hour to 15 hours. However, in the case of using the Swern oxidation reaction, the reaction temperature of reaction K is preferably about -80°C to -60°C.

[0184] The compound of formula (I-7) used in reaction K can be produced according to the above reaction G or a known method.

[0185] Reaction L is a Horner-Wadsworth-Emmons reaction. That is, reaction L can usually be carried out by mixing a compound of formula (I-11) with a compound of formula (X-6) in the presence of a solvent and a base. Relative to 1 equivalent of the compound of formula (I-11), 0.5 to 10 equivalents, preferably 1 to 5 equivalents of the compound of formula (X-6) can be used.

[0186] For the base, for example, one or more of metal amine salts such as lithium diisopropylamide and lithium bis(trimethylsilyl)amide, metal hydrides such as sodium hydride and potassium hydride, and metal alkoxides such as potassium tert-butoxide and lithium tert-butoxide can be appropriately selected and used in combination. 1 to 10 equivalents, preferably 1 to 5 equivalents of the base can be used relative to 1 equivalent of the compound of formula (I-11).

[0187] The solvent may be any solvent as long as it is inert to the reaction. For example, one or more solvents may be appropriately selected from aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; aliphatic hydrocarbons such as carbon tetrachloride, hexane, and cyclohexane; and ethers such as dioxane, tetrahydrofuran, diethyl ether, and dimethoxyethane.

[0188] The reaction temperature of Reaction L is about -100°C to 100°C, preferably about -80°C to 50°C, and the reaction time is usually about 10 minutes to 30 hours, preferably about 1 hour to 15 hours.

[0189] The compound of formula (X-6) used in reaction L can be a commercially available product.

[0190] [Reaction M]

[0191] Reaction M is a method of reacting a compound of formula (II-1) with a compound of formula (X-7) to obtain a compound of formula (III).

[0192]

[0193] The symbols in the formula are as described above.

[0194] Reaction M can be carried out according to the above-mentioned reaction A. Relative to 1 equivalent of the compound of formula (II-1), 0.5 to 10 equivalents, preferably 1 to 5 equivalents of the compound of formula (X-7) can be used. Relative to 1 equivalent of the compound of formula (II-1), 0.5 to 10 equivalents, preferably 1 to 5 equivalents of the base can be used. Relative to 1 equivalent of the compound of formula (II-1), 0.5 to 10 equivalents, preferably 1 to 5 equivalents of the dehydration condensation agent can be used, and relative to 1 equivalent of the compound of formula (II-1), 0.1 to 10 equivalents, preferably 1 to 5 equivalents of the additive can be used.

[0195] The compound of formula (II-1) used in reaction M can be produced by the following reaction 1-5 or a known method. The compound of formula (X-7) used in reaction M can be a commercially available product.

[0196] [Reaction N]

[0197] Reaction N is a method of reducing a compound of formula (III-1), a compound of formula (III-2), a compound of formula (III-3) or a compound of formula (III-4) to obtain a compound of formula (I-13).

[0198]

[0199] wherein E is H, C1-C6 alkyl or halogen, and other symbols are as described above.

[0200] Reaction N can be carried out according to the above-mentioned reaction G. The reducing agent can be used in an amount of 0.5 to 10 equivalents, preferably 1 to 5 equivalents, based on 1 equivalent of each compound of formula (III-1) to (III-4).

[0201] The compounds of formula (III-1) to (III-4) used in reaction N can be produced according to the above reaction M or a known method.

[0202] [Reaction O]

[0203] Reaction O is a Horner-Wadsworth-Emmons reaction, which is a method of reacting a compound of formula (III-1) with a compound of formula (X-6) to obtain a compound of formula (I-14). It is also a method of reacting a compound of formula (III-2) with a compound of formula (X-6) to obtain a compound of formula (I-15). It is also a method of reacting a compound of formula (III-3) with a compound of formula (X-6) to obtain a compound of formula (I-16). It is also a method of reacting a compound of formula (III-4) with a compound of formula (X-6) to obtain a compound of formula (I-17).

[0204]

[0205] The symbols in the formula are as described above.

[0206] Reaction O can be carried out according to the above-mentioned reaction L. For 1 equivalent of the compound of formula (III-1) as a raw material, 0.5 to 10 equivalents, preferably 1 to 5 equivalents of the compound of formula (X-6) can be used. For 1 equivalent of the compound of formula (III-1), 1 to 10 equivalents, preferably 1 to 5 equivalents of the base can be used. When the raw material is changed to a compound of formula (III-2) to a compound of formula (III-4), the compound of formula (X-6) and the base can also be used in the same equivalents as above.

[0207] The compounds of formula (III-1) to (III-4) used in reaction O can be produced according to the above reaction M or a known method. The compound of formula (X-6) used in reaction O can be a commercially available product.

[0208] [Reaction P]

[0209] Reaction P is a method of hydrolyzing a compound of formula (I-12) to obtain a compound of formula (I-18).

[0210]

[0211] The symbols in the formula are as described above.

[0212] Reaction P can be carried out according to the above reaction B. When a base is used in reaction P, the base can be used in an amount of 1 to 10 equivalents, preferably 1 to 5 equivalents, relative to 1 equivalent of the compound of formula (I-12). When an acid is used in reaction P, the acid can be used in an amount of 0.1 to 30 equivalents, preferably 1 to 10 equivalents, relative to 1 equivalent of the compound of formula (I-12).

[0213] [Reaction Q] and [Reaction R]

[0214] Reaction Q is a method of obtaining a compound of formula (I-19) by hydrogenating a compound of formula (I-12). Reaction R is a method of obtaining a compound of formula (I-20) by hydrolyzing a compound of formula (I-19).

[0215]

[0216] The symbols in the formula are as described above.

[0217] Reaction Q can be generally carried out by hydrogenating the compound of formula (I-12) using palladium carbon as a catalyst in the presence of a solvent under a hydrogen atmosphere. 0.001 to 1 equivalent, preferably 0.01 to 0.5 equivalent, of palladium carbon can be used relative to 1 equivalent of the compound of formula (I-12).

[0218] The solvent may be any solvent as long as it is inert to the reaction. For example, one or more solvents may be appropriately selected from ethers such as dioxane, tetrahydrofuran, diethyl ether, and dimethoxyethane; esters such as methyl acetate and ethyl acetate; alcohols such as methanol, ethanol, and isopropanol; and water.

[0219] The reaction temperature of reaction Q is about -20°C to 150°C, preferably about 0°C to 100°C, and the reaction time is usually about 0.5 to 48 hours. Alternatively, the reaction may be carried out under pressure as required.

[0220] Reaction R can be carried out according to the above reaction B. When a base is used in reaction R, the base can be used in an amount of 1 to 10 equivalents, preferably 1 to 5 equivalents, relative to 1 equivalent of the compound of formula (I-19). When an acid is used in reaction R, the acid can be used in an amount of 0.1 to 30 equivalents, preferably 1 to 10 equivalents, relative to 1 equivalent of the compound of formula (I-19).

[0221] [Reaction S] and [Reaction T]

[0222] Reaction S is a method for reacting a compound of formula (I-11) with Ohira-Bestmann reagent to obtain a compound of formula (I-21). Reaction T is a method for reacting a compound of formula (I-21) with a compound of formula (X-9) to obtain a compound of formula (I-22).

[0223]

[0224] The symbols in the formula are as described above.

[0225] Reaction S can be generally performed by mixing the compound of formula (I-11) with Ohira-Bestmann reagent in the presence of a solvent and a base.

[0226] The Ohira-Bestmann reagent in reaction S is dimethyl (1-diazo-2-oxopropyl)phosphonate. The Ohira-Bestmann reagent can be used in an amount of 0.5 to 10 equivalents, preferably 1 to 5 equivalents, relative to 1 equivalent of the compound of formula (I-11).

[0227] For the base, for example, carbonates such as sodium carbonate and potassium carbonate; bicarbonates such as sodium bicarbonate and potassium bicarbonate; metal hydrides such as sodium hydride and potassium hydride; amines such as triethylamine and N,N-diisopropylethylamine; pyridines such as pyridine, 4-dimethylaminopyridine and 2,6-lutidine; alkali metal carboxylates such as sodium acetate and potassium acetate, etc., can be appropriately selected or mixed for use. Relative to 1 equivalent of the compound of formula (I-11), 0.5 to 10 equivalents, preferably 1 to 5 equivalents of the base can be used.

[0228] The solvent may be any solvent as long as it is inert to the reaction, for example, one or more solvents may be appropriately selected from aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; aliphatic hydrocarbons such as carbon tetrachloride, chloroform, dichloromethane, dichloroethane, trichloroethane, hexane, and cyclohexane; ethers such as dioxane, tetrahydrofuran, diethyl ether, and dimethoxyethane; esters such as methyl acetate and ethyl acetate; aprotic polar solvents such as dimethyl sulfoxide, cyclopentane, N,N-dimethylacetamide, N,N-dimethylformamide, N-methylpyrrolidone, pyridine, acetonitrile, and propionitrile; ketones such as acetone and methyl ethyl ketone; and protic polar solvents such as methanol and ethanol.

[0229] The reaction temperature of Reaction S is about -30°C to 120°C, preferably about 0°C to 80°C, and the reaction time is usually about 10 minutes to 30 hours, preferably about 30 minutes to 15 hours.

[0230] The Ohira-Bestmann reagent used in Reaction S may also be a commercially available product.

[0231] Reaction T can usually be carried out by mixing the compound of formula (I-21) with the compound of formula (X-9) in the presence of a solvent and a base. 0.5 to 10 equivalents, preferably 1 to 5 equivalents of the compound of formula (X-9) can be used relative to 1 equivalent of the compound of formula (I-21).

[0232] For the base, for example, one or more of metal amine salts such as lithium diisopropylamide and lithium bis(trimethylsilyl)amide, metal hydrides such as sodium hydride and potassium hydride, and metal alkoxides such as potassium tert-butoxide and lithium tert-butoxide can be appropriately selected and used in combination. 1 to 10 equivalents, preferably 1 to 5 equivalents of the base can be used relative to 1 equivalent of the compound of formula (I-21).

[0233] The solvent may be any solvent as long as it is inert to the reaction. For example, one or more solvents may be appropriately selected from aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; aliphatic hydrocarbons such as hexane and cyclohexane; and ethers such as dioxane, tetrahydrofuran, diethyl ether, and dimethoxyethane.

[0234] The reaction temperature of reaction T is about -100°C to 100°C, preferably about -80°C to 50°C, and the reaction time is usually about 10 minutes to 30 hours, preferably about 1 hour to 15 hours.

[0235] The compound of formula (X-9) used in reaction T can be a commercially available product.

[0236] [Reaction U], [Reaction V], [Reaction W], and [Reaction X]

[0237] Reaction U is a method for reacting a compound of formula (I-2) with a compound of formula (X-10) to obtain a compound of formula (I-23). ​​Reaction V is a method for reacting a compound of formula (I-23) with an oxidant to obtain a compound of formula (I-24). Reaction W is a method for reacting a compound of formula (I-24) with a compound of formula (X-11) to obtain a compound of formula (I-25).

[0238] Reaction X is a method of obtaining a compound of formula (I-26) by reacting a compound of formula (I-24) with a reducing agent.

[0239]

[0240] The symbols in the formulae are as described above.

[0241] Reaction U can usually be carried out by mixing the compound of formula (I-2) with the compound of formula (X-10) in the presence of a solvent, a dehydrating condensation agent and a base. Relative to 1 equivalent of the compound of formula (I-2), 0.5 to 10 equivalents, preferably 1 to 5 equivalents of the compound of formula (X-10) can be used.

[0242] For the base, for example, one or more of carbonates such as sodium carbonate and potassium carbonate; bicarbonates such as sodium bicarbonate and potassium bicarbonate; metal hydroxides such as sodium hydroxide and potassium hydroxide; metal hydrides such as sodium hydride and potassium hydride; amines such as triethylamine and N,N-diisopropylethylamine; pyridines such as pyridine, 4-dimethylaminopyridine and 2,6-lutidine; alkali metal carboxylates such as sodium acetate and potassium acetate can be appropriately selected and used in combination. The base can be used in an amount of 0.5 to 10 equivalents, preferably 1 to 5 equivalents, relative to 1 equivalent of the compound of formula (I-2).

[0243] The solvent may be any solvent as long as it is inert to the reaction, for example, one or more solvents may be appropriately selected from aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; aliphatic hydrocarbons such as carbon tetrachloride, chloroform, dichloromethane, dichloroethane, trichloroethane, hexane, and cyclohexane; ethers such as dioxane, tetrahydrofuran, diethyl ether, and dimethoxyethane; esters such as methyl acetate and ethyl acetate; and aprotic polar solvents such as dimethyl sulfoxide, cyclopentane, N,N-dimethylacetamide, N,N-dimethylformamide, N-methylpyrrolidone, pyridine, acetonitrile, and propionitrile.

[0244] As the dehydration condensation agent, a carbodiimide condensation agent such as N,N'-dicyclohexylcarbodiimide (DCC), 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide (EDC) or its hydrochloride; an imidazole condensation agent such as 1,1'-carbonyldiimidazole (CDI); a triazine condensation agent such as 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (DMT-MM); a 1H-benzotriazol-1-yloxytripyrrolidinophosphonium hexafluorophosphate (P Phosphonium condensation agents such as phosphonium condensation agents such as 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate (HATU); anhydrides such as 2-methyl-6-nitrobenzoic anhydride (MNBA); 2-halogenopyridinium salts such as 2-chloro-1-methylpyridinium p-toluenesulfonate; propylphosphonic anhydride (cyclic trimer) (T3P); diphenylphosphoryl azide (DPPA), etc., are appropriately selected and used in combination. If necessary, conventional additives such as 1-hydroxybenzotriazole (HOBt) and 4-N,N-dimethylaminopyridine (DMAP) used together with the dehydration condensation agent can be added. When an additive is used in reaction U, the additive can be appropriately selected and used in combination of one or more. The dehydration condensation agent can be used in an amount of 0.5 to 10 equivalents, preferably 1 to 5 equivalents, relative to 1 equivalent of the compound of formula (I-2). The additive can be used in an amount of 0.1 to 10 equivalents, preferably 1 to 5 equivalents, relative to 1 equivalent of the compound of formula (I-2).

[0245] The reaction temperature of Reaction U is about -30°C to 120°C, preferably about 0°C to 80°C, and the reaction time is usually about 10 minutes to 30 hours, preferably about 30 minutes to 15 hours.

[0246] The compound of formula (X-10) used in reaction U can be produced by the method described in the supporting information of Journal of the American Chemical Society 2008, 130, 4253-4255 or an equivalent method.

[0247] Reaction V can generally be carried out by mixing the compound of formula (I-23) and an oxidizing agent in the presence of a solvent.

[0248] The oxidant is not particularly limited as long as the reaction proceeds, and examples thereof include potassium persulfate salts such as potassium persulfate (OXONE). The oxidant can be used in an amount of 0.5 to 30 equivalents, preferably 1 to 10 equivalents, relative to 1 equivalent of the compound of formula (I-23).

[0249] The solvent may be any solvent as long as it is inert to the reaction, for example, one or more solvents may be appropriately selected from aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; aliphatic hydrocarbons such as carbon tetrachloride, chloroform, dichloromethane, dichloroethane, trichloroethane, hexane, and cyclohexane; ethers such as dioxane, tetrahydrofuran, diethyl ether, and dimethoxyethane; esters such as methyl acetate and ethyl acetate; aprotic polar solvents such as dimethyl sulfoxide, cyclopentane, N,N-dimethylacetamide, N,N-dimethylformamide, N-methylpyrrolidone, pyridine, acetonitrile, and propionitrile; ketones such as acetone and methyl ethyl ketone; protic polar solvents such as methanol and ethanol; water, etc.

[0250] The reaction temperature of Reaction V is about -80°C to 100°C, preferably about 0°C to 50°C, and the reaction time is usually about 10 minutes to 30 hours, preferably about 1 hour to 15 hours.

[0251] Reaction W can be generally carried out by mixing the compound of formula (I-24) with the compound of formula (X-11) in the presence of a solvent and a base. 0.5 to 10 equivalents, preferably 1 to 5 equivalents of the compound of formula (X-11) can be used relative to 1 equivalent of the compound of formula (I-24).

[0252] For the base, for example, carbonates such as sodium carbonate and potassium carbonate; bicarbonates such as sodium bicarbonate and potassium bicarbonate; metal hydrides such as sodium hydride and potassium hydride; amines such as triethylamine and N,N-diisopropylethylamine; pyridines such as pyridine, 4-dimethylaminopyridine and 2,6-lutidine; alkali metal carboxylates such as sodium acetate and potassium acetate, etc., can be appropriately selected or mixed for use. Relative to 1 equivalent of the compound of formula (I-24), 0.5 to 10 equivalents, preferably 1 to 5 equivalents of the base can be used.

[0253] The solvent may be any solvent as long as it is inert to the reaction, for example, one or more solvents may be appropriately selected from aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; aliphatic hydrocarbons such as carbon tetrachloride, chloroform, dichloromethane, dichloroethane, trichloroethane, hexane, and cyclohexane; ethers such as dioxane, tetrahydrofuran, diethyl ether, and dimethoxyethane; esters such as methyl acetate and ethyl acetate; aprotic polar solvents such as dimethyl sulfoxide, cyclopentane, N,N-dimethylacetamide, N,N-dimethylformamide, N-methylpyrrolidone, pyridine, acetonitrile, and propionitrile; ketones such as acetone and methyl ethyl ketone; and protic polar solvents such as methanol and ethanol.

[0254] The reaction temperature of Reaction W is about -30°C to 120°C, preferably about 0°C to 80°C, and the reaction time is usually about 10 minutes to 30 hours, preferably about 30 minutes to 15 hours.

[0255] Reaction X can be carried out according to the above-mentioned reaction G. The reducing agent can be used in an amount of 0.5 to 10 equivalents, preferably 1 to 5 equivalents, based on 1 equivalent of the compound of formula (I-24).

[0256] [Reaction Y]

[0257] Reaction Y can usually be carried out by mixing the compound of formula (I-11) with an alcohol and an acid in the presence of a solvent.

[0258]

[0259] In the formula, R Y represents 1,3-dioxolane-2-yl or -CH(OL 2 )2(L 2 As described above), and other symbols are as described above.

[0260] Examples of the alcohol include methanol, ethanol, ethylene glycol, etc. The alcohol can be used in a ratio of 1 equivalent to a large excess relative to 1 equivalent of the compound of formula (I-11).

[0261] For the acid, for example, organic acids such as formic acid, acetic acid, methanesulfonic acid, p-toluenesulfonic acid, trifluoroacetic acid, trifluoromethanesulfonic acid, and inorganic acids such as hydrochloric acid, sulfuric acid, and hydrogen bromide can be cited, but are not limited to these. As the acid, one or more of these acids can be appropriately selected and used in combination. Relative to 1 equivalent of the compound of formula (I-11), 0.01 to 30 equivalents, preferably 0.1 to 10 equivalents of the acid can be used.

[0262] The solvent may be any solvent as long as it is inert to the reaction. For example, one or more solvents may be appropriately selected from aromatic hydrocarbons such as benzene and toluene.

[0263] The reaction temperature of Reaction Y is about -30°C to 150°C, preferably about 30°C to 100°C, and the reaction time is usually about 10 minutes to 30 hours, preferably about 30 minutes to 15 hours.

[0264] [Reaction Z] and [Reaction AA]

[0265] Reaction Z is a Horner-Wadsworth-Emmons reaction, which is a method of reacting a compound of formula (III) with a compound of formula (X-12) to obtain a compound of formula (I-29). Reaction AA is a method of hydrogenating a compound of formula (I-29) to obtain a compound of formula (I-30).

[0266]

[0267] The symbols in the formulae are as described above.

[0268] Reaction Z can be carried out according to the above reaction L. The compound of formula (X-12) can be used in an amount of 0.5 to 10 equivalents, preferably 1 to 5 equivalents, relative to 1 equivalent of the compound of formula (III). The base can be used in an amount of 1 to 10 equivalents, preferably 1 to 5 equivalents, relative to 1 equivalent of the compound of formula (III).

[0269] Reaction AA can be carried out according to the above-mentioned reaction Q. Palladium carbon can be used in an amount of 0.001 to 1 equivalent, preferably 0.01 to 0.5 equivalent, based on 1 equivalent of the compound of formula (I-29).

[0270] [Reaction AB] and [Reaction AC]

[0271] Reaction AB is a method for reacting a compound of formula (I-13) with a halogenating agent to obtain a compound of formula (I-31). Reaction AC is a method for coupling a compound of formula (I-31) with a compound of formula (X-13) to obtain a compound of formula (I-32).

[0272]

[0273] In the formula, G A is 2-thiazolyl or can be replaced by at least one Z 4 The substituted 2-imidazolyl group and other symbols are as described above.

[0274] Reaction AB can be carried out according to the above reaction I. The halogenating agent can be used in an amount of 0.5 to 10 equivalents, preferably 1 to 5 equivalents, relative to 1 equivalent of the compound of formula (I-13). In addition, in this reaction AB, when triphenylphosphine is used, the triphenylphosphine can be used in an amount of 0.5 to 10 equivalents, preferably 1 to 5 equivalents, relative to 1 equivalent of the compound of formula (I-13). In addition, the base can be used in an amount of 0.1 to 10 equivalents, preferably 1 to 5 equivalents, relative to 1 equivalent of the compound of formula (I-13).

[0275] Reaction AC can usually be carried out by mixing a compound of formula (I-31) with a compound of formula (X-13) in the presence of a solvent, a reducing agent and a catalyst. It should be noted that for reaction AC, a ligand can be added as needed. Relative to 1 equivalent of the compound of formula (I-31), 0.5 to 10 equivalents, preferably 1 to 3 equivalents of the compound of formula (X-13) can be used.

[0276] The reducing agent includes metals such as zinc and manganese, and one or more of them can be appropriately selected and used in combination. 1 to 10 equivalents, preferably 1 to 5 equivalents of the reducing agent can be used per 1 equivalent of the compound of formula (I-31).

[0277] The catalyst may be selected from nickel(II) chloride ethylene glycol dimethyl ether complex, nickel iodide, etc. or mixed. 0.002 to 1 equivalent, preferably 0.02 to 0.4 equivalent of the catalyst may be used relative to 1 equivalent of the compound of formula (I-31).

[0278] The ligand may be selected from 2,2'-bipyridine, 4,4'-dimethyl-2,2'-bipyridine, 4,4'-di-tert-butyl-2,2'-bipyridine, 1,10-phenanthroline, etc., or two or more thereof may be mixed and used. The ligand may be used in an amount of 0.002 to 1 equivalent, preferably 0.02 to 0.4 equivalent, relative to 1 equivalent of the compound of formula (I-31).

[0279] The solvent may be any solvent as long as it is inert to the reaction, for example, one or more solvents may be appropriately selected from aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; aliphatic hydrocarbons such as carbon tetrachloride, chloroform, dichloromethane, dichloroethane, trichloroethane, hexane, and cyclohexane; ethers such as dioxane, tetrahydrofuran, diethyl ether, and dimethoxyethane; esters such as methyl acetate and ethyl acetate; aprotic polar solvents such as dimethyl sulfoxide, sulfolane, N,N-dimethylacetamide, N,N-dimethylformamide, N-methylpyrrolidone, pyridine, acetonitrile, and propionitrile; and ketones such as acetone and methyl ethyl ketone.

[0280] The reaction temperature of reaction AC is about -30°C to 150°C, preferably about 0°C to 100°C, and the reaction time is usually about 2 hours to 80 hours, preferably about 10 hours to 50 hours.

[0281] The compound of formula (X-13) used in reaction AC can be a commercially available product. The compound of formula (I-32) can be produced by the method described in The Journal of Organic Chemistry 2014, 79, 4793 or an equivalent method, or can be produced according to a known method.

[0282] The compounds used in Production Method A (Reaction A to Reaction Z and Reaction AA to Reaction AC) can be produced by the production method of the following Production Method B (Reaction 1-1 to Reaction 1-16). However, the present invention is not limited to these methods, and these compounds can be produced by known methods, or commercially available products can be used.

[0283] Manufacturing method B

[0284] [Reaction 1-1] to [Reaction 1-3]

[0285] Reaction 1-1 is a Horner-Wadsworth-Emmons reaction, which is a method for reacting a compound of formula (VI) with a compound of formula (X-6) to obtain a compound of formula (V). Reaction 1-2 is a method for hydrolyzing a compound of formula (V) to obtain a compound of formula (IV). Reaction 1-3 is a method for reacting a compound of formula (VI) with malonic acid to obtain a compound of formula (IV).

[0286]

[0287] The symbols in the formula are as described above.

[0288] Reaction 1-1 can be carried out according to the above reaction L. The compound of formula (X-6) can be used in an amount of 0.5 to 5 equivalents, preferably 1 to 3 equivalents, relative to 1 equivalent of the compound of formula (VI). The base can be used in an amount of 1 to 10 equivalents, preferably 1 to 5 equivalents, relative to 1 equivalent of the compound of formula (VI).

[0289] Reaction 1-2 can be carried out according to the above reaction B. When a base is used in reaction 1-2, 1 to 10 equivalents, preferably 1 to 5 equivalents, can be used relative to 1 equivalent of the compound of formula (V). When an acid is used in reaction 1-2, 0.1 to 30 equivalents, preferably 1 to 10 equivalents, can be used relative to 1 equivalent of the compound of formula (V).

[0290] Reaction 1-3 can be generally carried out by mixing the compound of formula (VI) and malonic acid in the presence of a solvent and adding a base as required. Malonic acid can be used in an amount of 0.5 to 10 equivalents, preferably 1 to 5 equivalents, per equivalent of the compound of formula (VI).

[0291] The base may be selected from carbonates such as sodium carbonate and potassium carbonate; bicarbonates such as sodium bicarbonate and potassium bicarbonate; metal hydroxides such as sodium hydroxide and potassium hydroxide; metal hydrides such as sodium hydride and potassium hydride; amines such as triethylamine and N,N-diisopropylethylamine; pyridines such as pyridine, 4-dimethylaminopyridine and 2,6-lutidine; alkali metal carboxylates such as sodium acetate and potassium acetate, etc. or two or more thereof may be mixed and used. The base may be used in an amount of 0.01 to 10 equivalents, preferably 0.1 to 5 equivalents, relative to 1 equivalent of the compound of formula (VI).

[0292] The solvent may be any solvent as long as it is inert to the reaction, for example, one or more solvents may be appropriately selected from aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; aliphatic hydrocarbons such as hexane and cyclohexane; ethers such as dioxane, tetrahydrofuran, diethyl ether, and dimethoxyethane; aprotic polar solvents such as dimethyl sulfoxide, cyclopentane, N,N-dimethylacetamide, N,N-dimethylformamide, N-methylpyrrolidone, pyridine, acetonitrile, and propionitrile; and protic polar solvents such as methanol and ethanol.

[0293] The reaction temperature of Reaction 1-3 is about 0°C to 180°C, preferably about 30°C to 130°C, and the reaction time is usually about 10 minutes to 30 hours, preferably about 1 hour to 15 hours.

[0294] The compound of formula (VI) used in the above reaction 1-1 and reaction 1-3 can be prepared by the method described in The Journal of Organic Chemistry 2000, 65, 9120-9124 or an equivalent method, or a commercial product can be used. The compound of formula (X-6) used in reaction 1-1 can be a commercial product.

[0295] [Reaction 1-4]

[0296] Reaction 1-4 is a method of reacting a compound of formula (IV) with a compound of formula (X-8) to obtain a compound of formula (VII).

[0297]

[0298] The symbols in the formula are as described above.

[0299] Reaction 1-4 can usually be carried out by mixing the compound of formula (IV) and the compound of formula (X-8) in the presence of a solvent, an additive and a catalyst. It should be noted that for reaction 1-4, a ligand can be added as needed. Relative to 1 equivalent of the compound of formula (IV), 0.5 to 10 equivalents, preferably 1 to 3 equivalents of the compound of formula (X-8) can be used.

[0300] The additive may be selected from dimethyl phosphite, diethyl phosphite, triethylsilane, sodium dithionite, bis(pinacolato)diboron, etc., or two or more thereof may be mixed and used. The additive may be used in an amount of 1 to 10 equivalents, preferably 1 to 5 equivalents, relative to 1 equivalent of the compound of formula (IV).

[0301] The catalyst may be selected from copper oxide, copper iodide, copper thiocyanate, copper trifluoromethanesulfonate, etc., or a mixture of two or more thereof. 0.002 to 1 equivalent, preferably 0.02 to 0.4 equivalent of the catalyst may be used per 1 equivalent of the compound of formula (IV).

[0302] As the ligand, for example, one or more of 2,2'-bipyridine, 4,4'-dimethyl-2,2'-bipyridine, 4,4'-di-tert-butyl-2,2'-bipyridine, 1,10-phenanthroline, etc. can be appropriately selected and used in combination. The ligand can be used in an amount of 0.002 to 1 equivalent, preferably 0.02 to 0.4 equivalent, relative to 1 equivalent of the compound of formula (IV).

[0303] The solvent may be any solvent as long as it is inert to the reaction, for example, one or more solvents may be appropriately selected from aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; aliphatic hydrocarbons such as carbon tetrachloride, chloroform, dichloromethane, dichloroethane, trichloroethane, hexane, and cyclohexane; ethers such as dioxane, tetrahydrofuran, diethyl ether, and dimethoxyethane; esters such as methyl acetate and ethyl acetate; aprotic polar solvents such as dimethyl sulfoxide, sulfolane, N,N-dimethylacetamide, N,N-dimethylformamide, N-methylpyrrolidone, pyridine, acetonitrile, and propionitrile; and ketones such as acetone and methyl ethyl ketone.

[0304] The reaction temperature of reaction 1-4 is about -30°C to 150°C, preferably about 0°C to 100°C, and the reaction time is usually about 2 hours to 80 hours, preferably about 10 hours to 50 hours.

[0305] The compound of formula (IV) used in reaction 1-4 can be produced according to the above reaction 1-2 or a known method. A commercially available product can be used as the compound of formula (X-8).

[0306] [Reaction 1-5] to [Reaction 1-6]

[0307] Reaction 1-5 is a method for obtaining a compound of formula (II-1) by hydrolyzing a compound of formula (VII). Reaction 1-6 is a method for obtaining a compound of formula (II-2) by reacting a compound of formula (II-1) with a halogenating agent.

[0308]

[0309] Where V 2 is a chlorine atom or a bromine atom. Other symbols are as described above.

[0310] Reaction 1-5 can be carried out according to the above reaction B. When a base is used in reaction 1-5, 1 to 10 equivalents, preferably 1 to 5 equivalents, can be used relative to 1 equivalent of the compound of formula (VII). When an acid is used in reaction 1-5, 0.1 to 30 equivalents, preferably 1 to 10 equivalents, can be used relative to 1 equivalent of the compound of formula (VII).

[0311] The compound of formula (VII) used in Reaction 1-5 can be produced according to the above-mentioned Reaction 1-4 or a known method.

[0312] Reaction 1-6 can usually be carried out by mixing the compound of formula (II-1) and a halogenating agent in the presence of a solvent.

[0313] As for the halogenating agent, one or more of them can be appropriately selected from sulfur halides such as thionyl chloride; phosphorus halides such as phosphorus trichloride and phosphorus pentachloride; a reactant combining carbon tetrachloride, carbon tetrabromide and triphenylphosphine (Appel reaction); acyl halides such as oxalyl chloride and benzoyl chloride, etc., or a mixture of two or more can be used. Conventional additives used together with the halogenating agent such as N,N-dimethylformamide can also be added as needed.

[0314] The halogenating agent can be used in an amount of 0.5 to 100 equivalents, preferably 1 to 10 equivalents, relative to 1 equivalent of the compound of formula (II-1). The additive can be used in an amount of 0.001 to 50 equivalents, preferably 0.01 to 15 equivalents, relative to 1 equivalent of the compound of formula (II-1).

[0315] The solvent may be any solvent as long as it is inert to the reaction, for example, one or more solvents may be appropriately selected from aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; aliphatic hydrocarbons such as carbon tetrachloride, chloroform, dichloromethane, dichloroethane, trichloroethane, hexane, and cyclohexane; ethers such as dioxane, tetrahydrofuran, diethyl ether, and dimethoxyethane; and esters such as methyl acetate and ethyl acetate.

[0316] The reaction temperature of Reaction 1-6 is about -30°C to 150°C, preferably about -10°C to 80°C, and the reaction time is usually about 10 minutes to 30 hours, preferably about 30 minutes to 15 hours.

[0317] The compound of formula (II-1) used in Reaction 1-6 can be produced according to the above-mentioned Reaction 1-5 or a known method.

[0318] [Reaction 1-7]

[0319] Reaction 1-7 is a method of obtaining a compound of formula (VII) by reacting a compound of formula (VIII) with a compound of formula (X-8).

[0320]

[0321] The symbols in the formula are as described above.

[0322] Reaction 1-7 can be carried out by mixing a compound of formula (VIII) and a compound of formula (X-8) in the presence of a base, a catalyst and a solvent. 0.5 to 10 equivalents, preferably 1 to 3 equivalents, of the compound of formula (X-8) can be used relative to 1 equivalent of the compound of formula (VIII).

[0323] The base may be selected from carbonates such as sodium carbonate and potassium carbonate; bicarbonates such as sodium bicarbonate and potassium bicarbonate; metal hydroxides such as sodium hydroxide and potassium hydroxide; metal hydrides such as sodium hydride and potassium hydride; amines such as triethylamine, N,N-diisopropylethylamine, N,N,N',N'-tetramethylethylenediamine, N,N,N',N'-tetramethyl-1,3-propylenediamine, and pentamethyldiethylenetriamine; pyridines such as pyridine, 4-dimethylaminopyridine, and 2,6-lutidine; alkali metal carboxylates such as sodium acetate and potassium acetate, etc. or two or more thereof may be used in combination. The base may be used in an amount of 0.5 to 10 equivalents, preferably 1 to 5 equivalents, relative to 1 equivalent of the compound of formula (VIII).

[0324] The catalyst may be selected from copper (I) chloride, copper (I) bromide, copper (II) bromide, copper iodide, copper (II) trifluoromethanesulfonate, etc., or a mixture of two or more thereof. 0.002 to 1 equivalent, preferably 0.02 to 0.2 equivalent, of the catalyst may be used relative to 1 equivalent of the compound of formula (VIII).

[0325] The solvent may be any solvent as long as it is inert to the reaction, for example, one or more solvents may be appropriately selected from aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; aliphatic hydrocarbons such as carbon tetrachloride, chloroform, dichloromethane, dichloroethane, trichloroethane, hexane, and cyclohexane; ethers such as dioxane, tetrahydrofuran, diethyl ether, and dimethoxyethane; esters such as methyl acetate and ethyl acetate; aprotic polar solvents such as dimethyl sulfoxide, sulfolane, N,N-dimethylacetamide, N,N-dimethylformamide, N-methylpyrrolidone, pyridine, acetonitrile, and propionitrile; and ketones such as acetone and methyl ethyl ketone.

[0326] The reaction temperature of Reaction 1-7 is about -30°C to 150°C, preferably about 0°C to 100°C, and the reaction time is usually about 10 minutes to 30 hours, preferably about 2 hours to 24 hours.

[0327] The compound of formula (X-8) used in reaction 1-7 can be a commercial product. The compound of formula (VIII) can be prepared by the method described in Chemical Science 2019, 10, 8331-8337 or an equivalent method thereof, or a commercial product can be used, or it can be prepared according to a known method.

[0328] [Reaction 1-8] and [Reaction 1-9]

[0329] Reaction 1-8 is a method for reacting a compound of formula (VII-2) with a formylating agent to obtain a compound of formula (IX). Reaction 1-9 is a method for reacting a compound of formula (IX) with a Wittig reagent or Ohira-Bestmann reagent to obtain a compound of formula (IV-3).

[0330]

[0331] Wherein G is (C2-C6)-alkenyl or (C2-C6)-alkynyl, and other symbols are as described above.

[0332] Reaction 1-8 can usually be carried out by mixing the compound of formula (VII-2) with a formylating agent in the presence of a solvent and a base.

[0333] The formylating agent may be selected from, for example, N,N-dimethylformamide, N,N-disubstituted formamides such as N-formylmorpholine; orthoformates such as ethyl orthoformate; N-ethoxymethyleneaniline, etc., or a mixture of two or more thereof. The formylating agent may be used in an amount of 0.5 to 5 equivalents, preferably 1 to 3 equivalents, relative to 1 equivalent of the compound of formula (VII-2).

[0334] The base may be selected from metal amine salts such as lithium diisopropylamide and lithium bis(trimethylsilyl)amide; metal hydrides such as sodium hydride and potassium hydride; metal alkoxides such as potassium tert-butoxide and lithium tert-butoxide; metal alkyl salts such as methyl lithium and n-butyl lithium, or a mixture of two or more thereof. The base may be used in an amount of 0.5 to 5 equivalents, preferably 1 to 3 equivalents, relative to 1 equivalent of the compound of formula (VII-2).

[0335] The solvent may be any solvent as long as it is inert to the reaction. For example, one or more solvents may be appropriately selected from aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; aliphatic hydrocarbons such as carbon tetrachloride, hexane, and cyclohexane; and ethers such as dioxane, tetrahydrofuran, diethyl ether, and dimethoxyethane.

[0336] The reaction temperature of Reaction 1-8 is about -100°C to 50°C, preferably about -80°C to 30°C, and the reaction time is usually about 10 minutes to 30 hours, preferably about 1 hour to 15 hours.

[0337] The compound of formula (VII-2) used in Reaction 1-8 can be produced according to the above-mentioned Reaction 1-4 or a known method.

[0338] Reaction 1-9 can be generally performed by mixing the compound of formula (IX) with a Wittig reagent or Ohira-Bestmann reagent in the presence of a solvent and a base.

[0339] When a Wittig reagent is used in reaction 1-9, examples of the Wittig reagent include, but are not limited to, methyltriphenylphosphonium bromide and ethyltriphenylphosphonium bromide. 0.5 to 10 equivalents, preferably 1 to 5 equivalents of the Wittig reagent can be used relative to 1 equivalent of the compound of formula (IX).

[0340] The Ohira-Bestmann reagent in reaction 1-9 refers to dimethyl (1-diazo-2-oxopropyl)phosphonate. When the Ohira-Bestmann reagent is used, 0.5 to 10 equivalents, preferably 1 to 5 equivalents, can be used relative to 1 equivalent of the compound of formula (IX).

[0341] The base may be selected from carbonates such as sodium carbonate and potassium carbonate; bicarbonates such as sodium bicarbonate and potassium bicarbonate; metal hydrides such as sodium hydride and potassium hydride; amines such as triethylamine and N,N-diisopropylethylamine; pyridines such as pyridine, 4-dimethylaminopyridine and 2,6-lutidine; alkali metal carboxylates such as sodium acetate and potassium acetate, etc. or two or more thereof may be mixed and used. The base may be used in an amount of 0.5 to 10 equivalents, preferably 1 to 5 equivalents, relative to 1 equivalent of the compound of formula (IX).

[0342] The solvent may be any solvent as long as it is inert to the reaction, for example, one or more solvents may be appropriately selected from aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; aliphatic hydrocarbons such as carbon tetrachloride, chloroform, dichloromethane, dichloroethane, trichloroethane, hexane, and cyclohexane; ethers such as dioxane, tetrahydrofuran, diethyl ether, and dimethoxyethane; esters such as methyl acetate and ethyl acetate; aprotic polar solvents such as dimethyl sulfoxide, cyclopentane, N,N-dimethylacetamide, N,N-dimethylformamide, N-methylpyrrolidone, pyridine, acetonitrile, and propionitrile; ketones such as acetone and methyl ethyl ketone; and protic polar solvents such as methanol and ethanol.

[0343] The reaction temperature of Reaction 1-9 is about -30°C to 120°C, preferably about 0°C to 80°C, and the reaction time is usually about 10 minutes to 30 hours, preferably about 30 minutes to 15 hours.

[0344] As the Wittig reagent and Ohira-Bestmann reagent used in Reaction 1-9, commercially available products can be used.

[0345] [Reaction 1-10]~[Reaction 1-12]

[0346] Reaction 1-10 is a method for reacting a compound of formula (IX) with a Wittig reagent to obtain a compound of formula (XI-1). Reaction 1-11 is a method for reacting a compound of formula (XI-1) with an acid to obtain a compound of formula (XI-2). Reaction 1-12 is a method for reacting a compound of formula (XI-2) with a fluorinating agent to obtain a compound of formula (XI-3).

[0347]

[0348] The symbols in the formula are as described above.

[0349] Reaction 1-10 can be carried out according to the above reaction 1-9.

[0350] For example, Wittig reagents include (methoxymethyl)triphenylphosphonium chloride, but are not limited thereto. 0.5 to 10 equivalents, preferably 1 to 5 equivalents of Wittig reagent can be used relative to 1 equivalent of the compound of formula (IX). 0.5 to 5 equivalents, preferably 1 to 3 equivalents of the base can be used relative to 1 equivalent of the compound of formula (IX).

[0351] The compound of formula (IX) used in Reaction 1-10 can be produced according to the above-mentioned Reaction 1-8 or a known method.

[0352] Reaction 1-11 can usually be carried out by mixing the compound of formula (XI-1) and an acid in the presence of a solvent.

[0353] As for the acid, for example, organic acids such as formic acid, acetic acid, methanesulfonic acid, p-toluenesulfonic acid, trifluoroacetic acid, trifluoromethanesulfonic acid, and inorganic acids such as hydrochloric acid, sulfuric acid, and hydrogen bromide can be cited, but are not limited to these. As the acid, one or more of these acids can be appropriately selected and used in combination. Relative to 1 equivalent of the compound of formula (XI-1), 0.1 to 30 equivalents, preferably 1 to 10 equivalents of the acid can be used.

[0354] The solvent may be any solvent as long as it is inert to the reaction, for example, one or more solvents may be appropriately selected from aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; aliphatic hydrocarbons such as hexane and cyclohexane; ethers such as dioxane, tetrahydrofuran, diethyl ether, and dimethoxyethane; non-protonic polar solvents such as acetonitrile, N,N-dimethylformamide, dimethyl sulfoxide, N,N-dimethylacetamide, hexamethylphosphoric acid triamide, and cyclopentane sulfone; protonic polar solvents such as methanol, ethanol, and isopropanol; water, etc.

[0355] The reaction temperature of Reaction 1-11 is about -30°C to 150°C, preferably about 30°C to 100°C, and the reaction time is usually about 10 minutes to 30 hours, preferably about 30 minutes to 15 hours.

[0356] Reaction 1-12 can usually be carried out by mixing the compound of formula (XI-2) and a fluorinating agent in the presence of a solvent.

[0357] For the fluorinating agent, for example, N, N-dimethylamino sulfur trifluoride (DAST), bis (2-methoxyethyl) amino sulfur trifluoride, 1,1,2,2-tetrafluoro-N, N-dimethylethylamine (TFEDMA), (diethylamino) difluorotetrafluoroborate sulfonium salt (XtalFluor), 4-tert-butyl-2,6-dimethylphenyl sulfur trifluoride (FluoLead), 2-chloro-1,3-bis (2,6-diisopropylphenyl) -1H-imidazolium chloride (PhenoFluor), etc. can be listed, but are not limited to these. As a fluorinating agent, one or more of these substances can be appropriately selected for use in combination. Relative to 1 equivalent of the compound of formula (XI-2), 0.1 to 30 equivalents, preferably 1 to 10 equivalents of the fluorinating agent can be used.

[0358] The solvent may be any solvent as long as it is inert to the reaction, for example, one or more solvents may be appropriately selected from aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; aliphatic hydrocarbons such as carbon tetrachloride, chloroform, dichloromethane, dichloroethane, trichloroethane, hexane, and cyclohexane; ethers such as dioxane, tetrahydrofuran, diethyl ether, and dimethoxyethane.

[0359] The reaction temperature of reaction 1-12 is about -30°C to 150°C, preferably about 0°C to 80°C, and the reaction time is usually about 10 minutes to 30 hours, preferably about 30 minutes to 15 hours.

[0360] [Reaction 1-13] to [Reaction 1-16]

[0361] Reaction 1-13 is a method for reacting a compound of formula (IX) with a reducing agent to obtain a compound of formula (XI-4). Reaction 1-14 is a method for reacting a compound of formula (XI-4) with a halogenating agent to obtain a compound of formula (XI-5). Reaction 1-15 is a method for reacting a compound of formula (XI-5) with a nucleophilic reagent to obtain a compound of formula (XI-6). Reaction 1-16 is a method for reacting a compound of formula (XI-5) with a cyaniding agent to obtain a compound of formula (XI-7).

[0362]

[0363] The symbols in the formula are as described above.

[0364] Reaction 1-13 can be carried out according to the above reaction G. The reducing agent can be used in an amount of 0.5 to 10 equivalents, preferably 1 to 5 equivalents, relative to 1 equivalent of the compound of formula (IX).

[0365] Reaction 1-14 can be carried out according to the above reaction I. The halogenating agent can be used in an amount of 0.5 to 10 equivalents, preferably 1 to 5 equivalents, relative to 1 equivalent of the compound of formula (XI-4). In addition, when triphenylphosphine is used in this reaction 1-14, the triphenylphosphine can be used in an amount of 0.5 to 10 equivalents, preferably 1 to 5 equivalents, relative to 1 equivalent of the compound of formula (XI-4). In addition, the base can be used in an amount of 0.1 to 10 equivalents, preferably 1 to 5 equivalents, relative to 1 equivalent of the compound of formula (XI-4).

[0366] Reaction 1-15 can usually be carried out by mixing the compound of formula (XI-5) and a nucleophilic reagent in the presence of a solvent.

[0367] The nucleophilic agent can be selected from alkali metal alkoxides such as sodium methoxide and sodium ethoxide, or two or more can be mixed and used. 0.1 to 30 equivalents, preferably 1 to 10 equivalents of the nucleophilic agent can be used per 1 equivalent of the compound of formula (XI-5).

[0368] The solvent may be any solvent as long as it is inert to the reaction, for example, one or more solvents may be appropriately selected from aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; aliphatic hydrocarbons such as carbon tetrachloride, chloroform, dichloromethane, dichloroethane, trichloroethane, hexane, and cyclohexane; ethers such as dioxane, tetrahydrofuran, diethyl ether, and dimethoxyethane.

[0369] The reaction temperature of Reaction 1-15 is about -30°C to 150°C, preferably about 0°C to 80°C, and the reaction time is usually about 10 minutes to 30 hours, preferably about 30 minutes to 15 hours.

[0370] Reaction 1-16 can be carried out according to the above-mentioned reaction J. The cyaniding agent can be used in an amount of 0.5 to 10 equivalents, preferably 1 to 5 equivalents, based on 1 equivalent of the compound of formula (XI-5).

[0371] Compound (I) as an active ingredient of the present composition can be used as an active ingredient of a herbicide capable of preventing and controlling a wide range of undesirable plants such as annual weeds and perennial weeds. In addition, compound (I) can be used as a herbicide in a wide range of time periods from before the emergence of undesirable plants to after the emergence of the plants. Moreover, the present composition can appropriately utilize treatment methods such as soil treatment, stem and leaf treatment, and flooding treatment, which are assumed to be practical scenarios of herbicides. Therefore, the present composition shows excellent efficacy as a herbicide in practical scenarios.

[0372] Specific examples of the undesirable plants include the following plants. For example, barnyardgrass (Echinochloa crus-galli), rice barnyardgrass (Echinochloa oryzicola), crabgrass (Digitaria sanguinalis, D. ischaemum, D. adscendens, D. microbachne, D. horizontalis), green foxtail (Setaria viridis), giant foxtail (Setaria faberi), yellow foxtail (Setaria lutescens), goosegrass (Eleusine indica), johnsongrass (Sorghumhalepense), quackgrass (Agropyron repens), alexandergrass (Brachiaria plantaginea), guineagrass (Panicum maximum), paragrass (Brachiaria mutica), smooth witchgrass (Panicum dichotomiflorum), sprangletop (Leptochloa chinensis), red sprangletop (Leptochloapanicea), annual bluegrass (Poa annua), roughstalk bluegrass (Poa trivialis), blackgrass (Alopecurus myosuroides), shortawn foxtail (Alopecurus aequalis), cholorado bluestem (Agroqyrontsukushiense), broadleaf signalgrass (Brachiaria platyphylla), southern thorngrass ( sandbur (Cenchrus echinatus)), multiflora ryegrass (Italianryegrass (Lolium multiflorum), rigid ryegrass (Lolium rigidum), perennial ryegrass (Lolium perenne), wild oat (Avena fatua), black oat (Avenastrigosa), field brome (Bromus arvensis), rescuegrass (Bromus catharticus Vahl), hairy chess (Bromus commutatus), smooth brome (Bromus inermis), Japanese brome (Bromus japonicus), compact brome (Bromus madritensis), soft chess (Bromus mollis), ripgut brome (Bromus rigidus), red brome (Bromus serratus), and serratus. brome (Bromus rubens), cheat grass (Bromus secalinus), poverty brome (Bromus sterilis), downy brome (Bromus tectorum), windgrass (Apera spica-venti), littleseed canarygrass (Phalaris minor), rattail fescue (Festucamyuros), cheat grass (Bromus tectorum), Bermuda grass (Cynodondactylon); rice flatsedge (Cyperus iria), purple nutsedge (Cyperus rotundus), yellow nutsedge (Cyperusesculentus), rock bulrush (Schoenoplectus juncoides)), water sedge (tidalmarshflatsedge (Cyperus)serotinus), small-flower umbrellaplant (Cyperusdifformis), needle spikerush (Eleocharis acicularis), waterchestnut (Eleocharis kuroguwai) and other weeds in the Cyperaceae family; dwarfarrowhead (Sagittaria pygmaea), threeleaf arrowhead (Sagittariatrifolia), channelled water plantain (Alisma canaliculatum) and other weeds in the Alismataceae family; monochoria (Monochoria vaginalis), heartshape false pickerelweed (Monochoria korsakowii) and other weeds in the Pontederiaceae family; false pimpernel (Lindernia pyxidaria); Plantaginaceae such as dopatrium (Dopatrium junceum) and common fieldspeedwell (Veronica persica); Lythraceae such as indiantoothcup (Rotala India) and manyflower ammannia (Ammannia multiflora); Elastaceae such as long stem waterwort (Elatinetriandra); Malvaceae such as velvetleaf (Abutilontheophrasti) and prickly sida (Sida spinosa); Common cocklebur (Xanthium strumarium), common ragweed (Ambrosia elatior) and Canada thistle (Cirsiumarvense), hairy galinsoga (Galinsoga ciliata), wild chamomile (Matricariachamomilla), henbit (Lamium amplexicaule), common dandelion (Taraxacum officinale), horseweed (Conyza canadensis); solanaceae weeds (solanaceae) such as black nightshade (Solanum nigrum) and jimsonweed (Daturastramonium); slender amaranth (Amaranthus viridis), redroot pigweed (Amaranthus retroflexus), common lambsquarters (Chenopodium album), mexican burningbush (Kochia scoparia) of the Amaranthaceae family; pale smartweed (Polygonumlapathifolium), ladysthumb (Polygonumpersicaria), wild buckwheat (Polygonumconvolvulus), knotweed (Polygonumaviculare) of the Polygonaceae family; flexuous bittercress (Cardamineflexuosa), shepherd's-purse (Capsellabursa-pastoris), wild mustard (Sinapisarvensis), Indian mustard (Brassicajuncea) of the Cruciferae family; tall morningglory (Ipomoea purpurea)), fieldbindweed (Convolvulus arvensis), ivyleafmorningglory (Ipomoeahederacea); portulacaceae such as common purslane (Portulacaoleracea); fabaceae such as Cassia obtusifolia; caryophyllaceae such as common chickweed (Stellaria media); rubiaceae such as catchweed (Galium spurium); euphorbiaceae such as threeseeded copperleaf (Acalypha australis); commelinaceae such as common dayflower (Commelina communis); red deadnettle (Lamium purpureum) and other noxious weeds such as lamiaceae.

[0373] Since the compound (I) can control the above-mentioned various harmful weeds, the present composition can be effectively used in the cultivation of useful plants, either in the case of selectively controlling harmful weeds or in the case of non-selectively controlling harmful weeds.

[0374] Specific examples of the useful plants include the following plants. Examples include corn (Zea mays), soybean (Glycine max), cotton (Gossypium spp.), wheat (Triticum aestivum), rice (Oryza sativa), barley (Hordeum vulgare), rye (Secale cereale), oats (Avena sativa), sorghum (Sorghum bicolor), rape (Brassica napus), sunflower (Helianthus annuus), sugar beet (Beta vulgaris), sugar cane (Saccharum officinarum), Japanese lawn grass (Zoysia japonica steud.), peanut (Arachis hypogaea), flax (Linum usitatissimum), tobacco (Nicotiana tabacum), coffee (Coffea spp.), apple (Malus pumila), Japanese pear (Pyrus pyrifolia), pear (Pyrus communis), loquat (Japanesemedlar (Eriobotrya japonica), peach (Prunus persica), nectarine (Nectaris nipponica, var.nectarina), Japanese apricot (Prunus mume), cherry (Prunus avium), apricot (Prunus armeniaca), plum (Prunus domestica), Satsuma mandarin (Citrus unshiu), orange (Citrus sinensis), lemon (Citrus limon), lime (Citrus aurantiifolia), grapefruit (Citrus paradisi), blueberry (Vaccinium spp.), blackberry (Rubus fruticosus), raspberry (Rubus idaeus), grape (Vitis vinifera), chestnut (Castanea crenata), walnut (Juglans spp.), almond (Amygdalus dulcis)), pistachio (Pistaciavera)), cashew (Anacardium occidentale)), macadamia nut (Macadamiaintegrifolia)), persimmon (Diospyros kaki Thunb.)), olive (Oleaeuropaea)), banana (Musa spp.)), date palm (Phoenix dactylifera)), oil palm (Elaeis spp.) etc. .

[0375] The composition can be applied to harmful weeds, useful plants or soil to prevent and control various undesirable plants. The soil includes soil where plants grow or can grow. For example, the composition can be used to prevent and control harmful weeds in agricultural land such as paddy fields and dry fields, grasslands, non-agricultural land such as roadsides, etc.

[0376] The above-mentioned useful plants include plants that have been endowed with tolerance to herbicides such as HPPD inhibitors such as isoxathiapiprolin, ALS inhibitors such as imazapyr and thifensulfuron-methyl, EPSP synthase inhibitors such as glyphosate, glutamine synthetase inhibitors such as glufosinate, acetyl CoA carboxylase inhibitors such as sethoxydim, PPO inhibitors such as fluazifop, bromoxynil, dicamba, 2,4-D, etc. through classical breeding methods. Specifically, corn, rapeseed, wheat, sunflower, rice (trade name: Clearfield 5000) that are tolerant to imidazolinone herbicides can be cited. TM ); STS soybeans tolerant to sulfonylurea ALS-inhibiting herbicides; SR corn tolerant to acetyl-CoA carboxylase inhibitors such as triketoximes and aryloxyphenoxypropionic acid herbicides.

[0377] The above-mentioned useful plants also include transformed plants created using gene recombination technology and genome editing technology. For example, they include plants endowed with environmental stress tolerance, herbicide tolerance, pest tolerance, disease tolerance, etc., and plants with changes in growth, reproductive traits, product quality, yield, etc. Moreover, the above-mentioned useful plants also include composite varieties that combine these multiple useful traits.

[0378] Examples of transformed plants imparted with herbicide tolerance include glyphosate-tolerant corn, soybean, cotton, rapeseed, and sugar beet varieties (trade name: Roundup Ready TM 、Agrisure TM 、Gly-Tol TM ); glufosinate-tolerant corn, soybean, cotton, and rapeseed varieties (trade name: Liberty Link TM ); bromoxynil-resistant cotton varieties (trade name: BXN), etc.

[0379] Examples of transformed plants that have been endowed with pest resistance include plants that can synthesize toxins known in the genus Bacillus, etc. The toxins synthesized by plants bred using these genetic recombination technologies and genome editing technologies can impart resistance to coleopteran pests, hemipteran pests, dipteran pests, lepidopteran pests, and nematodes.

[0380] Examples of such toxins include insecticidal proteins from Bacillus cereus or Bacillus cinerea; delta-endotoxins such as Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C, insecticidal proteins such as VIP1, VIP2, VIP3 or VIP3A from Bacillus thuringiensis; insecticidal proteins from nematodes; toxins produced by animals such as scorpion toxins, spider toxins, bee toxins or insect-specific neurotoxins; filamentous fungal toxins; plant lectins; lectins; trypsin inhibitors, filamentous protease inhibitors such as amino acid protease inhibitors, batastatins, cysteine ​​protease inhibitors, papain inhibitors; ribosome inactivating proteins (RIPs) such as ricin, abrin, lupin, saporin, and dioscorea toxin; steroid metabolic enzymes such as 3-hydroxysteroid oxidase, ecdysteroid-UDP-glucosyltransferase, and cholesterol oxidase; ecdysone inhibitors; HMG-CoA reductase; ion channel inhibitors such as sodium channel and calcium channel inhibitors; juvenile hormone esterase; diuretic hormone receptor; stilbene synthase; bibenzyl synthase; chitinase; glucanase, etc. In addition, such toxins also include mixed toxins, partially deleted toxins, and modified toxins of δ-endotoxin proteins such as Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1, Cry9C, Cry34Ab, or Cry35Ab, and insecticidal proteins such as VIP1, VIP2, VIP3, or VIP3A.

[0381] Examples of transformed plants related to plant components include plants with modified oil content or enhanced amino acid content. Specifically, examples include low-flax soybeans with reduced flax content (trade name: VISTIVE TM ), corn varieties with increased lysine or oil content, etc.

[0382] Examples of plant pathogen-resistant transformed plants include plants imparted with the ability to produce a selectively acting anti-pathogenic substance.

[0383] The present composition is usually prepared by mixing compound (I) with a solid carrier or a liquid carrier, and adding surfactants and other formulation adjuvants as needed to prepare powders, granules, powder granules, granule hydrates, hydrates, aqueous suspensions, oil suspensions, aqueous solvents, emulsions, liquids, pastes, aerosols, microspray preparations, microcapsules and the like. As long as they are suitable for the purpose of the present invention, all formulation forms commonly used in the art can be prepared.

[0384] Specific examples of the solid carrier include diatomaceous earth, slaked lime, carbonate, talc, white carbon, kaolin, bentonite, kaolinite, cellulose, clay, sodium bicarbonate, sodium sulfate, zeolite, starch, polycarboxylates, anhydrous sulfates, and dodecylbenzenesulfonates.

[0385] Specific examples of the above-mentioned liquid carrier include water, toluene, xylene, solvent naphtha, dioxane, acetone, isophorone, methyl isobutyl ketone, chlorobenzene, cyclohexane, dimethyl sulfoxide, dimethylformamide, dimethylacetamide, N-methyl-2-pyrrolidone, N,N-dimethylacetamide, diethylene glycol monoethyl ether and alcohols (for example, ethylene glycol, etc.).

[0386] Specific examples of the surfactant include fatty acid salts, benzoates, alkyl sulfosuccinates, dialkyl sulfosuccinates, polycarboxylates, alkyl sulfate ester salts, alkyl sulfates, alkyl aryl sulfates, alkyl diglycol ether sulfates, alcohol sulfate ester salts, alkyl sulfonates, alkyl aryl sulfonates, aryl sulfonates, alkyl diphenyl ether disulfonates, polystyrene sulfonates, alkyl phosphate ester salts, alkyl aryl phosphates, styrylaryl phosphates, polyoxyethylene alkyl ether sulfate ester salts, polyoxyethylene alkyl ether phosphates, polyoxyethylene alkyl aryl ether sulfates, polyoxyethylene alkyl aryl ether sulfates, polyoxyethylene alkyl ether phosphates, polyoxyethylene alkyl aryl phosphates, polyoxyethylene aryl ether phosphates, polyoxyethylene styrylphenyl anionic surfactants or spreading agents such as alkyl ether phosphates, naphthalene sulfonate formaldehyde condensates, alkyl naphthalene sulfonate formaldehyde condensates, alkyl naphthalene sulfonates, lignin sulfonates, and polyoxyethylene styryl phenyl ether sulfates; nonionic surfactants or spreading agents such as sorbitan fatty acid esters, glycerol fatty acid esters, fatty acid polyglycerol esters, fatty acid alcohol polyglycol ethers, acetylenic diols, acetylenic alcohols, oxyalkylene block polymers, polyoxyethylene alkyl ethers, polyoxyethylene alkyl aryl ethers, polyoxyethylene styryl aryl ethers, polyoxyethylene glycol alkyl ethers, polyethylene glycols, polyoxyethylene fatty acid esters, polyoxyethylene sorbitan fatty acid esters, polyoxyethylene glycerol fatty acid esters, polyoxyethylene hydrogenated castor oil, polyoxypropylene fatty acid esters, and polyoxyethylene styryl phenyl ethers.

[0387] Specific examples of other formulation adjuvants include vegetable oils or mineral oils such as olive oil, kapok oil, castor oil, palm oil, camellia oil, coconut oil, sesame oil, corn oil, rice bran oil, peanut oil, cottonseed oil, soybean oil, rapeseed oil, linseed oil, tung oil, liquid paraffin, silicone oil, and xanthan gum.

[0388] For each component in these adjuvants, as long as it does not depart from the purpose of the present invention, one or more than two kinds can be appropriately selected for use. In addition, in addition to the above-mentioned adjuvants, it is also possible to appropriately select and use from adjuvants known in the field, for example, various adjuvants commonly used such as extenders, thickeners, anti-settling agents, antifreeze agents, dispersion stabilizers, drug damage reduction agents, and antifungal agents can also be used. The proportion of compound (I) and various adjuvants is usually 0.1:99.9~95:5 by weight, preferably 0.2:99.8~85:15. When these preparations are actually used, they can be used directly, or diluted to a specified concentration using a diluent such as water, and various spreading agents (surfactants, vegetable oils, mineral oils, etc.) are added as needed and used.

[0389] The application of the present composition cannot be uniformly specified depending on the meteorological conditions, formulation form, target crop, application period, application site, type of noxious weeds, production conditions, etc., but the present composition or its dilution can usually be applied by conventional application methods, i.e., soil treatment, stem and leaf treatment, flooding treatment, etc. Usually, in the case of soil treatment, the application amount of the present composition is about 0.1 to 5000 g per hectare, and the application amount of compound (I) as the active ingredient of the present composition is about 0.001 to 4500 g per hectare. Usually, in the case of stem and leaf treatment, the application amount of the present composition is about 0.1 to 5000 g per hectare, and the application amount of compound (I) as the active ingredient of the present composition is about 0.001 to 4500 g per hectare. Usually, in the case of flooding treatment, the application amount of the present composition is about 0.1 to 5000 g per hectare, and the application amount of compound (I) as the active ingredient of the present composition is about 0.001 to 4500 g per hectare.

[0390] The soil treatment is a method of controlling undesirable plants by applying compound (I) to the soil in a place where useful plants grow or can grow. Specifically, there can be mentioned a treatment method in which a stock solution such as an emulsion, liquid, hydrate, or a solution diluted with water, granules, powders, or granules are spread on the soil surface, and a treatment method in which a stock solution such as an emulsion, liquid, hydrate, or a solution diluted with water, granules, powders, or granules are spread on the soil surface and then the soil is mixed using a machine or the like.

[0391] The above-mentioned foliage treatment can be a method of controlling harmful weeds by applying compound (I) to the whole or part of useful plants or harmful weeds. Here, part of useful plants or harmful weeds refers to all parts of useful plants or harmful weeds such as leaves, stems, branches, buds, flowers, or a combination thereof.

[0392] The flooding treatment is a method for controlling harmful weeds growing in a flooded paddy field where useful plants are growing or where useful plants are to be grown, or harmful weeds before germination. Specifically, there can be mentioned methods of spreading hydrates, granules, powders, or powder-granular agents on the edge or ridge of a paddy field, in a paddy field, at a water outlet, etc.

[0393] The present composition may be mixed or used in combination with other components selected from other agricultural and horticultural chemicals, fertilizers, and drug damage reducing agents. In this case, more excellent effects and functions may be exhibited.

[0394] The mixed use or combined use mentioned above means using the present composition and other components simultaneously, separately or with a time interval therebetween.

[0395] Other agricultural and horticultural agents include herbicides, insecticides, miticides, nematicides, soil insecticides, fungicides, antivirals, attractants, antibiotics, plant hormones, plant growth regulators, etc. In particular, the present composition and the mixed herbicidal compositions formed by mixing or using one or more of the active ingredient compounds of other herbicides can sometimes improve the scope of application, the time of agent treatment, the control activity, etc. in a preferred direction. In addition, for the present composition and the active ingredient compounds of other herbicides, each can be formed into a preparation separately and mixed for use when spreading, or the two can be formed into a preparation together and used. The present invention also includes such a mixed herbicide.

[0396] The mixing ratio of compound (I), other herbicides and active ingredient compounds depends on differences in meteorological conditions, formulation form, target crops, application period, application site, types of noxious weeds, production conditions, etc. and cannot be uniformly specified. In terms of weight ratio, it can usually be set to 1:0.001 to 1:10000, preferably 1:0.01 to 1:1000. In addition, regarding the application amount, the total amount of active ingredient compounds per hectare can be set to 0.1 to 10000 g, preferably 0.2 to 5000 g. The present invention also includes a method for controlling undesirable plants by applying such a mixed herbicidal composition.

[0397] When applying the herbicidal composition containing compound (I), other agricultural and horticultural agents such as fungicides, insecticides, miticides, nematicides, soil pesticides, antivirals, attractants, herbicides, plant growth regulators, etc. may also be used together.

[0398] The active ingredient compound (common name) of the herbicide in the above-mentioned other agricultural and horticultural agents can be appropriately selected from the following compound groups, for example. Even if not specifically described, when various structural isomers such as salts, alkyl esters, and optical isomers exist in these compounds, they are of course also included.

[0399] (1) 2-methyl-4-chloropropionic acid (mecoprop), 2-methyl-4-chloropropionic acid butoxyethyl ester (mecoprop-butotyl), 2-methyl-4-chloropropionic acid sodium (mecoprop-sodium), 2-methyl-4-chloropropionic acid (mecoprop-P), 2-methyl-4-chloropropionic acid butoxyethyl ester (mecoprop-P-butotyl), 2-methyl-4-chloropropionic acid dimethylammonium (mecoprop-P-dimethylammonium), 2-ethylhexyl 2-methyl-4-chloropropionic acid (mecoprop-P-2-ethylhexyl), 2-methyl-4-chloropropionic acid potassium (mecoprop-P-potassium), 2,4-dichlorprop, naproanilide, clomeprop, erbon, disul, disul-sodium, 2,4,5-fenoprop, HIA-1 and other phenoxy compounds;2,3,6-TBA, dicamba, dicamba-butotyl, dicamba-diglycolamine, dicamba-dimethylammonium, dicamba-diolamine, dicamba-isopropylammonium, dicamba-potassium, dicamba-sodium, chloramben, picloram, picloram-dimethylammonium, picloram-isoctyl, picloram-potassium, picloram-triisopropanolammonium, picloram-triisopropylammonium onium), picloram-trolamine, triclopyr, triclopyr-butotyl, triclopyr-triethylammonium, clopyralid, clopyralid-olamine, clopyralid-potassium, clopyralid-triisopropanolammonium, aminopyralid, aminocyclopyrachlor, halauxifen, halauxifen-methyl, florpyrauxifen, florpyrauxifen-benzyl, tricamba, DAS-534 and other aromatic carboxylic acid compounds;and cliodinate, naptalam, naptalam-sodium, benazolin, benazolin-ethyl, quinclorac, quinmerac, diflufenzopyr, diflufenzopyr-sodium, fluroxypyr, fluroxypyr-2-butoxy-1-methylethyl hyl), fluroxypyr-meptyl, chlorflurenol, chlorflurenol-methyl, clacyfos, aminocyclopyrachlor-methyl, aminocyclopyrachlor-potassium, fluchloraminopyr, indolauxipyr, etc., compounds that show herbicidal effects by disrupting the hormone action of plants. ;

[0400] (2) Chlorotoluron, diuron, fluometuron, linuron, metobromuron, monuron, isoproturon, metobenzuron, tebuthiuron, dimefuron, isouron, karbutilate, methabenzthiazuron, m etoxuron), buthiuron, monolinuron, neburon, buturon, chlorbromuron, chloreturon, chloroxuron, difenoxuron, ethidimuron, fenuron, fluothiuron, isonoruron, monoruon-TCA, cyclouron urea compounds such as siduron; terbumeton, trietazine, simazine, aziprotryne, chlorazine, cyprazine, desmetryn, dipropetryn, methoprene, proglinazine, proglinazine-ethyl, sebuthylazi triazine compounds such as ne), secbumeton, atrazine, atraton, simetryn, prometryn, dimethametryn, terbuthylazine, cyanazine, ametryn, cybutryne, terbutryn, propazine, cyanatryn, and prometon;Triazinones such as hexazinone, ametridione, amibuzin, ethiozin, isomethiozin, metribuzin and metamitron; uracils such as bromacil, bromacyl-lithium, lenacil, isocil and terbacil; aniline compounds such as propanil, chloranocryl, cypromid and pentanochlor; carbamates such as desmedipham, chlorprocarb, phenisopham and phenmedipham; bromoxynil and chlorprocarb; Hydroxybenzonitrile compounds such as bromoxynil, bromoxynil-octanoate, bromoxynil-heptanoate, chloroxynil, ioxynil, ioxynil-octanoate, ioxynil-potassium, and ioxynil-sodium; and compounds that exhibit herbicidal effects by inhibiting plant photosynthesis such as pyridate, bentazone, bentazone-sodium, amicarbazone, methazole, iodobonil, methiuron, pyridafol, tioclorim, and chloridazon. ;

[0401] (3) Quaternary ammonium salt compounds such as paraquat and diquat that become free radicals in plants and generate active oxygen to exhibit rapid herbicidal effects.

[0402] (4) chlornitrofen, fluorodifen, fluoronitrofen, furyloxyfen, halosafen, nitrofen, chlomethoxyfen, bifenox, acifluorfen, acifluorfen-sodium, fomesafen, fomesafen-sodium, oxyfluorfen, lactofen, benzaclostrobin Diphenyl ether compounds such as aclonifen, ethoxyfen-ethyl, fluoroglycofen-ethyl, and fluoroglycofen; cyclic imide compounds such as chlorphthalim, flumioxazin, flumiclorac, flumiclorac-pentyl, flumipropyn, cinidon-ethyl, fluthiacet-methyl, and EK-5385;and flupropacil, oxadiargyl, oxadiazon, sulfentrazone, carfentrazone-ethyl, thidiazimin, pentoxazone, azafenidin, pyraflufen-ethyl, benzfendizone, butafenacil, saflufenacil, fluazolate, profluazol, flupyridazine Compounds that exhibit herbicidal effects by inhibiting plant chlorophyll biosynthesis and abnormally accumulating photosensitive peroxidation substances in the plant body, such as fenpyr-ethyl, bencarbazone, tiafenacil, trifludimoxazin, epyrifenacil, pyraclonil, cyclopyranil, flufenoximacil, compound I described in International Publication No. 2007 / 101587, compound 1 described in International Publication No. 2000 / 050407, and compound 11 described in International Publication No. 2002 / 019825. ;

[0403] (5) pyridazinones such as norflurazon and metflurazon; pyrazoles such as pyrazolynate, pyrazoxyfen, benzofenap, topramezone, tripyrasulfone, fenpyrazone, cypyrafluone, pyrasulfotole, tolpyralate and pyraquinate;and bicyclopyrone, amitrole, flurochloridone, fluridone, flurtamone, diflufenican, methoxyphenone, clomazone, bixlozone, broclozone, mesotrione, tefuryltrione, fenquinotrione, cyclopyrimorate, difenzoquat, difenzoquat-metilsulfate, isoxachlortole, benzobicyclon, picolinafen, beflubutamid, S-fluorobutyric acid beflubutamid-M, benquitrione, 3-chloro-2-[3-(difluoromethyl)isoxazol-5-yl]phenyl 5-chloropyrimidin-2-yl ether (rimisoxafen), 2-(3,4-dimethoxyphenyl)-4-[(2-hydroxy-6-oxocyclohex-1-en-1-yl)carbonyl]-6-methylpyridazine-3(2H)-one (dioxopyritrione), quintrione, isoxaflutole Compounds that inhibit the biosynthesis of plant pigments such as carotenoids and exhibit herbicidal effects characterized by a bleaching effect, such as lancotrione, lancotrione-sodium, sulcotrione, tembotrione, ketospiradox, ketospiradox-potassium, iptriazopyrid, and flusulfinam. ;

[0404] (6) diclofop-methyl, diclofop, pyriphenop-sodium, fluazifop-butyl, fluazifop, fluazifop-P, fluazifop-P-butyl, fenthiaprop, fenthiaprop-ethyl, haloxyfop-methyl, haloxyfop, Haloxyfop-etotyl, haloxyfop-P, haloxyfop-P-methyl, quizalofop-ethyl, quizalofop-P, quizalofop-P-ethyl, quizalofop-P-tefuryl, cyhalofop-butyl, fenoxaprop-ethyl, fenoxaprop-P, fenoxaprop-P-methyl Aryloxyphenoxypropionic acid compounds such as fenoxaprop-P-ethyl, metamifop-propyl, metamifop, clodinafop-propargyl, clodinafop, propaquizafop, isoxapyrifop, trifop, trifop-methyl, trifopsime, HNPC-A8169, and SYP-1924; sodium thiophenesulfonate ( Cyclohexanedione compounds such as alloxydim-sodium, alloxydim, clethodim, sethoxydim, tralkoxydim, butroxydim, tepraloxydim, profoxydim, cycloxydim, and cloproxydim; phenylpyrazoline compounds such as pinoxaden, and the like, which exhibit herbicidal effects on plants by inhibiting the biosynthesis of fatty acids.

[0405] (7) Chlorimuron-ethyl, chlorimuron, sulfometuron-methyl, sulfometuron, primisulfuron-methyl, primisulfuron, bensulfuron-methyl, bensulfuron, chlorsulfuron, metsulfuron-methyl, metsulfuron, ether cinosulfuron, pyrazosulfuron-ethyl, pyrazosulfuron, flazasulfuron, rimsulfuron, nicosulfuron, imazosulfuron, flucetosulfuron, cyclosulfamuron, prosulfuron, flupyrsulfuron-methyl-sodium, fluorine flupyrsulfuron, triflusulfuron-methyl, triflusulfuron, halosulfuron-methyl, halosulfuron, thifensulfuron-methyl, thifensulfuron, ethoxysulfuron, oxasulfuron, ethametsulfuron, ethametsulphonyl ulfuron-methy1), iodosulfuron, iodosulfuron-methyl-sodium, sulfosulfuron, triasulfuron, tribenuron-methyl, tribenuron, tritosulfuron, foramsulfuron, trifloxysulfuron, trifloxysulfuron-sodium,Sulfonylurea compounds such as mesosulfuron-methyl, mesosulfuron, orthosulfamuron, amidosulfuron, azimsulfuron, propyrisulfuron, metazosulfuron, methiopyrsulfuron, monosulfuron-methyl, iofensulfuron, and iofensulfuron-sodium; triazole pyridine sulfonamides such as flumetsulam, metosulam, diclosulam, cloransulam-methyl, florasulam, penoxsulam, and pyroxsulam Sulfonamide compounds; imazapyr, imazapyr-isopropylammonium, imazethapyr, imazethapyr-ammonium, imazaquin, imazaquin-ammonium, imazamox, imazamox-ammonium, imazamethabenz, imazamethabenz-methyl, imazapic and other imidazolinone compounds; pyrithione sodium hiobac-sodium), bispyribac-sodium, pyriminobac-methyl, pyribenzoxim, pyriftalid and other pyrimidinyl salicylic acid compounds; flucarbazone, flucarbazone-sodium, propoxycarbazone-sodium, propoxycarbazone, thiencarbazone-methyl and other sulfonylaminocarbonyltriazolinone compounds; pyrimisulfan,Sulfonanilide compounds such as triafamone; and glyphosate, glyphosate-sodium, glyphosate-potassium, glyphosate-ammonium, glyphosate-diammonium, glyphosate-isopropylammonium, glyphosate-trimesium, glyphosate-sesquisodium ... Compounds that exhibit herbicidal effects by inhibiting the biosynthesis of amino acids in plants, such as esquisodium, glufosinate, glufosinate-ammonium, glufosinate-P, glufosinate-P-ammonium, glufosinate-P-sodium, bialafos, bialafos-sodium, cinmethylin, and pyriflubenzoxim.

[0406] (8) Dinitroaniline compounds such as trifluralin, oryzalin, nitralin, pendimethalin, ethalfluralin, benfluralin, prodiamine, profluralin, butralin, dinitramine, isopropalin, and fluchloralin; amide compounds such as bensulide, naproxamide, naproxamide-M, propyzamide, and pronamide; amiprofos-methyl, butamifos, DMPA, anilofos, piperophos, and chlorpyrifos; s); phenylcarbamate compounds such as propham, chlorpropham, barban, carbetamide and swep; propylphenylamine compounds such as daimuron, cumyluron, bromobutide and methyldymron; and compounds that exhibit herbicidal effects by inhibiting plant cell mitosis, such as chlorbufam, dithiopyr, thiazopyr, chlorthal-dimethyl, chlorthal, diphenamid, flamprop-M-methyl, flamprop-M and flamprop-M-isopropyl.

[0407] (9) alachlor, metazachlor, butachlor, pretilachlor, metolachlor, S-metolachlor, thenylchlor, pethoxamid, acetochlor, propachlor, dimethenamid, dimethenamid-P, propisochlor, Chloroacetamide compounds such as dimethachlor, delachlor, diethatyl, diethatyl-ethyl, prynachlor, and terbuchlor; molinate, dimepiperate, pyributicarb, EPTC, butylate, pebulate, cycloate, prosulfocarb, Thiocarbamate compounds such as esprocarb, thiobencarb, diallate, tri-allate, vernolate, tiocarbazil, orbencarb; and etobenzanid, mefenacet, flufenacet, tridiphane, indanofan, fentrazamide, cafenazole, etc. Compounds that exhibit herbicidal effects by inhibiting protein biosynthesis or lipid biosynthesis in plants include strole, ipfencarbazone, benfuresate, pyroxasulfone, fenoxasulfone, methiozolin, dalapon, dalapon-sodium, TCA-sodium, ethofumesate, and trichloroacetic acid.

[0408] (10) Compounds such as dichlobenil, triaziflam, indaziflam, flupoxam, isoxaben, and chlorthiamid that exhibit herbicidal effects by inhibiting plant cellulose biosynthesis.

[0409] (11) MSMA, DSMA, CMA, endothall, endothall-dipotassium, endothall-sodium, endothall-mono(N,N-dimethylalkylammonium), asulam, asulam-sodium, oxaziclomefone, tetflupyrolimet, sodium chlorate, pelargonic acid, nonanoic acid, fosamine, fosamine-ammonium, aclolein, ammonium sulfamate, borax, chloroacetic acid, sodium chloroacete, cyanamide, methylarsonic acid acid, dimethylarsinic acid, sodium dimethylarsinate, dinoterb, dinoterb-ammonium, dinoterb-diolamine, dinoterb-acetate, DNOC, dinoseb, ferrous sulfate, flupropanate, flupropanate-sodium, mefluidide, mefluidide-diolamine, metam, metam-ammonium, metam-potassium, metam-sodium, methylisothiocyanate, pentachlorophenol, sodium pentachlorophenoxide, pentachlorophenol laurate laurate), quinoclamine, sulfuric acid, urea sulfate,xanthinosin, herbimycin, unguinol, metatyrosine, sarmentine, thaxtomin A, mevalocidin, alpha-limonene, pyribambenz-propyl, pyribambenz-isopropyl, allidochlor, alorac, amidochlor, clodinal isuron、benzadox、benzadoxammonium、benzipram、benzofluor、benzoylprop、benzoylprop-ethyl、bromobonil、bromofenoxim、butenachlor、buthidazole、cambendichlor、carbasulam、carboxazole、 chlorazifop, chlorazifop-propargyl, chlorfenac, chlorfenac-salts, chlorfenprop, chlorfenprop-methyl, cisanilide, clofop, clofop-isobutyl, cloprop, credazine, cycluron, cyperquat, cyperquat chloride erquat-chloride), dazomet, dazomet-sodium, dichlormate, o-dichlorobenzene, diethamquat, difenopenten, difenopenten-ethyl, dimesulfazet, dimexano, dimidazon, dimethyldisulfide, dinofenate, dinosam,dipropalin, eglinazine, eglinazine-ethyl, ethachlor, etinofen, fenasulam, flumezin, fluoromidine, halosafen, haloxydine, hexachloroacetone, isocarbamid, isopolinate, menoterb, menoterb actate, monalide, morfamquat, morfamquat dichloride dichloride), noruron, oleic acid, oxapyrazon, perfluidone, pydanon, pyriclor, quinonamid, sulfallate, tebutam, tetrafluron, thiazafluron, thidiazuron, xylachlor, bipyrazone, aspartic acid, icafolin, compound A1 described in Japanese Patent Application Publication No. 2022 / 42267, compound 43 described in International Publication No. 2016 / 095768, compound I-1-1 described in International Publication No. 2012 / 065573, and other herbicides.

[0410] (12) Substances that exhibit herbicidal effects by parasitizing on plants, such as Xanthomonas campestris, Epicoccosirus nematosorus, Epicoccosirus nematosperus, Exserohilum monoseras, and Drechslela monoceras.

[0411] The above compounds as active ingredients of other herbicides can be selected one or two or more as appropriate. In addition, the active ingredients of other herbicides are not limited to the compounds exemplified above.

[0412] Preferred embodiments of the present invention are described below, but the present invention is not limited thereto.

[0413] [1] A herbicidal composition comprising the difluorocrotonamide compound represented by the above formula (I) or a salt thereof as an active ingredient.

[0414] [2] A method for controlling undesirable plants or inhibiting their growth, wherein an effective amount of the difluorocrotonamide compound represented by the above formula (I) or a salt thereof is applied to harmful weeds, useful plants, or soil.

[0415] [3] The difluorobutenamide compound represented by the above formula (I) or a salt thereof.

[0416] [4] A difluorocrotonamide compound represented by the above-mentioned formula (IAa), formula (IAb), formula (IBa), formula (IBb) or formula (IBc) or a salt thereof.

[0417] [5] A difluorocrotonamide compound represented by the above-mentioned formula (IAa), formula (IBa), formula (IBb) or formula (IBc) or a salt thereof.

[0418] [6] A difluorobutenamide compound represented by the above formula (IAa), formula (IBa) or formula (IBb) or a salt thereof.

[0419] [7] A difluorobutenamide compound represented by the above-mentioned formula (IAa), formula (IBa) or formula (IBc) or a salt thereof.

[0420] [8] A difluorobutenamide compound represented by the above formula (IAa), formula (IBb) or formula (IBc) or a salt thereof.

[0421] [9] A difluorobutenamide compound represented by the above-mentioned formula (IBa), formula (IBb) or formula (IBc) or a salt thereof.

[0422]

[10] A difluorobutenamide compound represented by the above formula (IAa) or (IBa) or a salt thereof.

[0423]

[11] A difluorocrotonamide compound represented by the above formula (IAa) or (IBb) or a salt thereof.

[0424]

[12] A difluorobutenamide compound represented by the above formula (IAa) or (IBc) or a salt thereof.

[0425]

[13] A difluorobutenamide compound represented by the above formula (IBa) or (IBb) or a salt thereof.

[0426]

[14] A difluorobutenamide compound represented by the above formula (IBa) or (IBc) or a salt thereof.

[0427]

[15] A difluorobutenamide compound represented by the above formula (IBb) or (IBc) or a salt thereof.

[0428]

[16] The difluorobutenamide compound represented by the above formula (IAa) or a salt thereof.

[0429]

[17] A difluorobutenamide compound represented by the above formula (IBa) or a salt thereof.

[0430]

[18] The difluorobutenamide compound represented by the above formula (IBb) or a salt thereof.

[0431]

[19] A difluorobutenamide compound represented by the above formula (IBc) or a salt thereof.

[0432]

[20] The difluorobutenamide compound or a salt thereof as described in [3] above, wherein the compound represented by the above formula (I) is a compound represented by the above formula (IAa) or (IBa).

[0433]

[21] The difluorobutenamide compound or a salt thereof according to [3] above, wherein the compound represented by the formula (I) is a compound represented by the formula (IAa) or (IBb).

[0434]

[22] The difluorobutenamide compound or a salt thereof as described in [3] above, wherein the compound represented by the above formula (I) is a compound represented by the above formula (IAa) or (IBc).

[0435]

[23] The difluorobutenamide compound or a salt thereof as described in [3] above, wherein the compound represented by the above formula (I) is a compound represented by the above formula (IBa) or (IBb).

[0436]

[24] The difluorobutenamide compound or a salt thereof as described in [3] above, wherein the compound represented by the above formula (I) is a compound represented by the above formula (IBa) or (IBc).

[0437]

[25] The difluorobutenamide compound or a salt thereof as described in [3] above, wherein the compound represented by the above formula (I) is a compound represented by the above formula (IBb) or (IBc).

[0438]

[26] The difluorobutenamide compound or a salt thereof as described in [3] above, wherein the compound represented by the above formula (I) is a compound represented by the above formula (IAa).

[0439]

[27] The difluorobutenamide compound or a salt thereof as described in [3] above, wherein the compound represented by the above formula (I) is a compound represented by the above formula (IBa).

[0440]

[28] The difluorobutenamide compound or a salt thereof according to [3] above, wherein the compound represented by the above formula (I) is a compound represented by the above formula (IBb).

[0441]

[29] The difluorobutenamide compound or a salt thereof as described in [3] above, wherein the compound represented by the above formula (I) is a compound represented by the above formula (IBc).

[0442]

[30] The difluorobutenamide compound or a salt thereof as described in [3] above, wherein when t is 1, the carbon-carbon bond in the dotted line portion is a single bond.

[0443]

[31] The difluorobutenamide compound or a salt thereof as described in [3] above, wherein t is 1 and the carbon-carbon bond in the dotted line portion is a single bond.

[0444]

[32] The difluorobutenamide compound or a salt thereof as described in [3] above, wherein t is 2 and the carbon-carbon bond in the dotted line portion is a single bond.

[0445]

[33] The difluorobutenamide compound or a salt thereof as described in [3] above, wherein t is 2, one of the carbon-carbon bonds in the dotted line portion is a single bond, and the other carbon-carbon bond in the dotted line portion is a double bond.

[0446]

[34] The difluorobutenamide compound or a salt thereof as described in [3] above, wherein t is 1, the carbon-carbon bond in the dotted line portion is a single bond, and R 4 The substitution is carried out at the 3-position on the cyclobutyl group.

[0447]

[35] The difluorobutenamide compound or a salt thereof as described in [3] above, wherein t is 2, the carbon-carbon bond in the dotted line portion is a single bond, and R 4 The substitution is carried out at the 3-position on the cyclopentyl group.

[0448]

[36] The difluorobutenamide compound or a salt thereof as described in

[10] above, wherein R in the compound (IAa) 4 Substitution at the 3-position of the cyclobutyl group, or R 4 The substitution is carried out at the 3-position on the cyclopentyl group.

[0449]

[37] The difluorobutenamide compound or a salt thereof as described in

[11] above, wherein R in the compound (IAa) 4 Substitution at the 3-position of the cyclobutyl group, or R in compound (IBb) 4 The substitution is carried out at the 3-position on the 4-cyclopentenyl group.

[0450]

[38] The difluorobutenamide compound or a salt thereof as described in

[12] above, wherein R in the compound (IAa) 4Substitution at the 3-position of the cyclobutyl group, or R in compound (IBc) 4 The substitution is carried out at the 3-position on the 3-cyclopentenyl group.

[0451]

[39] The difluorobutenamide compound or a salt thereof as described in

[13] above, wherein R in the compound (IBa) 4 Substitution at the 3-position of the cyclobutyl group, or R in compound (IBb) 4 The substitution is carried out at the 3-position on the 4-cyclopentenyl group.

[0452]

[40] The difluorobutenamide compound or a salt thereof as described in

[14] above, wherein R in the compound (IBa) 4 Substitution at the 3-position of the cyclopentyl group, or R in compound (IBc) 4 The substitution is carried out at the 3-position on the 3-cyclopentenyl group.

[0453]

[41] The difluorobutenamide compound or a salt thereof as described in

[15] above, wherein R in the compound (IBb) 4 Substitution at the 3-position of the 4-cyclopentenyl group or R in compound (IBc) 4 The substitution is carried out at the 3-position on the 3-cyclopentenyl group.

[0454]

[42] The difluorobutenamide compound or a salt thereof as described in

[16] above, wherein R in the compound (IAa) 4 The substitution is carried out at the 3-position on the cyclobutyl group.

[0455]

[43] The difluorobutenamide compound or a salt thereof as described in

[17] above, wherein R in the compound (IBa) 4 The substitution is carried out at the 3-position on the cyclopentyl group.

[0456]

[44] The difluorobutenamide compound or a salt thereof as described in

[18] above, wherein R in the compound (IBb) 4 The substitution is carried out at the 3-position on the 4-cyclopentenyl group.

[0457]

[45] The difluorobutenamide compound or a salt thereof as described in

[19] above, wherein R in the compound (IBc) 4 The substitution is carried out at the 3-position on the 3-cyclopentenyl group.

[0458]

[46] The difluorobutenamide compound or a salt thereof according to any one of [3] to

[45] above, wherein R 1 and R 2 Each is a halogen, may be replaced by at least one Y 1 Substituted (C1-C6)-chain hydrocarbon group, (C1-C6)-alkoxy group which may be substituted by at least one halogen, cyano group or H, Y1 It is a halogen.

[0459]

[47] The difluorobutenamide compound or a salt thereof according to any one of [3] to

[45] above, wherein R 1 and R 2 Each is a halogen, may be replaced by at least one Y 1 Substituted (C1-C6)-alkyl, (C1-C6)-alkoxy which may be substituted with at least one halogen, cyano or H, Y 1 It is a halogen.

[0460]

[48] ​​The difluorobutenamide compound or a salt thereof according to any one of [3] to

[45] above, wherein R 1 and R 2 Each is a halogen, may be replaced by at least one Y 1 Substituted (C1-C6)-alkyl, (C1-C6)-alkoxy which may be substituted with at least one halogen, cyano or H, Y 1 A fluorine atom.

[0461]

[49] The difluorobutenamide compound or a salt thereof as described in any one of [3] to

[45] above, wherein R 1 and R 2 Each is a fluorine atom, which may be replaced by at least one Y 1 Substituted (C1-C6)-alkyl, (C1-C6)-alkoxy which may be substituted with at least one halogen, cyano or H, Y 1 A fluorine atom.

[0462]

[50] The difluorobutenamide compound or a salt thereof according to any one of [3] to

[45] above, wherein R 1 and R 2 Each is a fluorine atom, a chlorine atom, and may be replaced by at least one Y 1 Substituted (C1-C6)-alkyl, cyano or H, Y 1 A fluorine atom.

[0463]

[51] The difluorobutenamide compound or a salt thereof according to any one of [3] to

[45] above, wherein R 1 and R 2 Each is halogen, methyl, ethyl, n-propyl, isopropyl, monofluoromethyl, difluoromethyl, trifluoromethyl, 2,2,2-trifluoroethyl, 2,2-difluoroethyl, 1,1-difluoroethyl, methoxy, ethoxy, isopropoxy, difluoromethoxy, trifluoromethoxy, 2,2-difluoroethoxy, cyano or H.

[0464]

[52] The difluorobutenamide compound or a salt thereof according to any one of [3] to

[45] above, wherein R 1 and R2 Each is halogen, methyl, difluoromethyl, trifluoromethyl, methoxy, trifluoromethoxy, cyano or H.

[0465]

[53] The difluorobutenamide compound or a salt thereof according to any one of [3] to

[45] above, wherein R 1 and R 2 Each is a fluorine atom, a methyl group, a 2,2-difluoroethyl group, a methoxy group, a trifluoromethoxy group, a cyano group or H.

[0466]

[54] The difluorobutenamide compound or a salt thereof according to any one of [3] to

[45] above, wherein R 1 and R 2 Each is a fluorine atom, a methyl group, a 2,2-difluoroethyl group, a methoxy group or H.

[0467]

[55] The difluorobutenamide compound or a salt thereof according to any one of [3] to

[45] above, wherein R 1 and R 2 Each is a fluorine atom, a chlorine atom, a difluoromethyl group, a trifluoromethyl group, a cyano group or H.

[0468]

[56] The difluorobutenamide compound or a salt thereof according to any one of [3] to

[45] above, wherein R 1 and R 2 Each is a fluorine atom, a chlorine atom, a methyl group or H.

[0469]

[57] The difluorobutenamide compound or a salt thereof according to any one of [3] to

[56] above, wherein R 3 For H.

[0470]

[58] The difluorobutenamide compound or a salt thereof according to any one of [3] to

[56] above, wherein R 3 A fluorine atom.

[0471]

[59] The difluorobutenamide compound or a salt thereof according to any one of [3] to

[58] above, wherein R 4 -C(=O)OR 5 、-C(=O)SR 6 、-C(=O)NR 7 R 8 、-C(=O)R 9 、-SR 6 、-S(=O)R 6 , can be at least one Z 3 Substituted (C1-C6)-chain hydrocarbon group, OH.

[0472]

[60] The difluorobutenamide compound or a salt thereof according to any one of [3] to

[58] above, wherein R4 -C(=O)OR 5 、-C(=O)SR 6 、-C(=O)NR 7 R 8 、-C(=O)R 9 , can be at least one Z 3 Substituted (C1-C6)-chain hydrocarbon group, or -CH(OH)-C(=O)R 11 .

[0473]

[61] The difluorobutenamide compound or a salt thereof according to any one of [3] to

[58] above, wherein R 4 -C(=O)OR 5 、-C(=O)NR 7 R 8 、-C(=O)R 9 or can be represented by at least one Z 3 Substituted (C1-C6)-chain hydrocarbon group.

[0474]

[62] The difluorobutenamide compound or a salt thereof according to any one of [3] to

[58] above, wherein R 4 -C(=O)OR 5 、-C(=O)SR 6 、-C(=O)NR 7 R 8 , can be at least one Z 3 Substituted (C1-C6)-alkyl, or -CH(OH)-C(=O)R 11 , Z 3 It is halogen, (C1-C6)-alkylsulfonyloxy.

[0475]

[63] The difluorobutenamide compound or a salt thereof according to any one of [3] to

[58] above, wherein R 4 -C(=O)OR 5 , can be at least one Z 3 Substituted (C1-C6)-alkyl, or -CH(OH)-C(=O)R 11 , Z 3 is halogen or (C1-C6)-alkylsulfonyloxy.

[0476]

[64] The difluorobutenamide compound or a salt thereof according to any one of [3] to

[63] above, wherein R 5 It is (C1-C6)-alkyl, H, (C3-C6)-cycloalkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl or a 4- to 6-membered oxygen-containing saturated heterocyclic ring.

[0477]

[65] The difluorobutenamide compound or a salt thereof according to any one of [3] to

[63] above, wherein R 5 It is (C1-C6)-alkyl.

[0478]

[66] The difluorobutenamide compound or a salt thereof according to any one of [3] to

[63] above, wherein R 5 is methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, 3,3-dimethylbutyl, n-pentyl, cyclopropyl, cyclopentyl, 2-propenyl, 2-butenyl, 3-butenyl, 2-propynyl, 2-butynyl, 3-butynyl, 3-oxetanyl, 3-tetrahydrofuranyl, or 4-tetrahydropyranyl.

[0479]

[67] The difluorobutenamide compound or a salt thereof according to any one of [3] to

[63] above, wherein R 5 It is methyl.

[0480]

[68] The difluorobutenamide compound or a salt thereof according to any one of [3] to

[63] above, wherein Z 1 It is cyano, halogen, (C1-C6)-alkylthio, (C1-C6)-alkylsulfonyl, (C1-C6)-alkoxy, phenyl, pyridyl, (C1-C6)-alkoxycarbonyl or 1,3-dioxolan-4-yl.

[0481]

[69] The difluorobutenamide compound or a salt thereof according to any one of [3] to

[63] above, wherein Z 1 It is cyano, halogen, (C1-C6)-alkylthio, (C1-C6)-alkylsulfonyl, (C1-C6)-alkoxy, or 1,3-dioxolan-4-yl.

[0482]

[70] The difluorobutenamide compound or a salt thereof as described in any one of [3] to

[63] above, wherein Z 1 It is a cyano group, a fluorine atom, a chlorine atom, a bromine atom, a methylthio group, a methylsulfonyl group, a methoxy group, a phenyl group, a 2-pyridyl group, a 3-pyridyl group, a 4-pyridyl group, a methoxycarbonyl group, or a 1,3-dioxan-4-yl group.

[0483]

[71] The difluorobutenamide compound or a salt thereof according to any one of [3] to

[60] ,

[62] and

[63] to

[69] , wherein R 6 is (C1-C6)-alkyl which may be substituted by at least one halogen.

[0484]

[72] The difluorobutenamide compound or a salt thereof according to any one of [3] to

[60] ,

[62] and

[63] to

[69] , wherein R 6is methyl, ethyl, trifluoromethyl, cyclopentyl, or benzyl.

[0485]

[73] The difluorobutenamide compound or a salt thereof according to any one of [3] to

[62] and

[64] to

[72] above, wherein R 7 can be represented by at least one Y 2 Substituted (C1-C6)-alkyl, H or (C1-C6)-alkoxy.

[0486]

[74] The difluorobutenamide compound or a salt thereof according to any one of [3] to

[62] and

[64] to

[72] above, wherein R 7 can be represented by at least one Y 2 Substituted (C1-C6)-alkyl, H or (C1-C6)-alkoxy, Y 2 is (C1-C6)-alkoxy, halogen, or cyano.

[0487]

[75] The difluorobutenamide compound or a salt thereof according to any one of [3] to

[62] and

[64] to

[72] above, wherein R 7 is (C1-C6)-alkyl, H or (C1-C6)-alkoxy.

[0488]

[76] The difluorobutenamide compound or a salt thereof according to any one of [3] to

[62] and

[64] to

[72] above, wherein R 7 is H, methyl, ethyl, n-propyl, n-pentyl, 2-propenyl, 2-propynyl, 2-chloroethyl, methylsulfonyl, OH, 2-methoxyethyl, 2-methylthioethyl, cyanomethyl, methoxycarbonylmethyl, ethoxycarbonylmethyl, tert-butoxycarbonylmethyl, 1-(methoxycarbonyl)ethyl, benzyl, methoxy, ethoxy, n-propoxy, isopropoxy, 2-propenyloxy, phenoxy, 3-pyridazinyl, or -(CH2)-(C=O)NH-(CH2)-C(=O)OCH3, in R 7 and R 8 When forming a fully saturated 4- to 6-membered ring together with the nitrogen to which they are bound, the 4- to 6-membered ring is 2-oxazolidinyl, 1,2-oxazinan-1-yl, 4-morpholino, 1-piperidinyl, 4-chloropiperidin-1-yl, 1-pyrrolidinyl, or 1-azetidinyl.

[0489]

[77] The difluorobutenamide compound or a salt thereof according to any one of [3] to

[62] and

[64] to

[76] above, wherein R 8 is H, or (C1-C6)-alkyl.

[0490]

[78] The difluorobutenamide compound or a salt thereof according to any one of [3] to

[62] and

[64] to

[76] above, wherein R 8 is H, methyl, ethyl, n-propyl, isopropyl, n-butyl or methoxy.

[0491]

[79] The difluorobutenamide compound or a salt thereof according to any one of [3] to

[61] and

[64] to

[78] above, wherein R 9 It is methyl, ethoxycarbonylmethyl or 1-imidazolyl.

[0492]

[80] The difluorobutenamide compound or a salt thereof according to any one of [3] to

[61] and

[64] to

[79] above, wherein Z 3 It is (C1-C6)-alkoxycarbonyl, or -C(=O)OH.

[0493]

[81] The difluorobutenamide compound or a salt thereof according to any one of [3] to

[61] and

[64] to

[79] above, wherein Z 3 It is OH, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a cyano group, a methoxy group, a methylsulfonyloxy group, an ethylsulfonyloxy group, an n-propylsulfonyloxy group, an isopropylsulfonyloxy group, an n-butylsulfonyloxy group, an acetoxy group, an ethylcarbonyloxy group, an isopropylcarbonyloxy group, a methoxycarbonyl group, an ethoxycarbonyl group, a tert-butoxycarbonyl group, or -C(=O)OH.

[0494]

[82] The difluorobutenamide compound or a salt thereof according to any one of [3] to

[58] ,

[60] and

[62] to

[81] above, wherein R 11 It is methyl or ethyl.

[0495]

[83] The difluorobutenamide compound or a salt thereof according to any one of [3] to

[82] above, wherein m is 1 or 2.

[0496]

[84] The difluorobutenamide compound or a salt thereof according to any one of [3] to

[82] above, wherein m is 1.

[0497]

[85] The difluorobutenamide compound or a salt thereof as described in [3] above, wherein R 4 -C(=O)OR 5 、-C(=O)SR 6 、-C(=O)NR 7 R 8 、-C(=O)R 9 , can be at least one Z 3 Substituted (C1-C6)-chain hydrocarbon group, or -CH(OH)-C(=O)R 11 , R 7can be represented by at least one Y 2 Substituted (C1-C6)-alkyl, H, or (C1-C6)-alkoxy, Z 3 It is (C1-C6)-alkoxycarbonyl, or -C(=O)OH.

[0498]

[86] The difluorobutenamide compound or a salt thereof as described in [3] above, wherein R 1 and R 2 Each is a halogen, may be replaced by at least one Y 1 Substituted (C1-C6)-alkyl, (C1-C6)-alkoxy which may be substituted with at least one halogen, cyano or H, Y 1 is halogen, R 4 -C(=O)OR 5 、-C(=O)SR 6 、-C(=O)NR 7 R 8 、-C(=O)R 9 , can be at least one Z 3 Substituted (C1-C6)-chain hydrocarbon group, or -CH(OH)-C(=O)R 11 , R 7 can be represented by at least one Y 2 Substituted (C1-C6)-alkyl, H, or (C1-C6)-alkoxy, Z 3 It is (C1-C6)-alkoxycarbonyl, or -C(=O)OH.

[0499]

[87] The difluorobutenamide compound or a salt thereof as described in [3] above, wherein R 1 and R 2 Each is a halogen, may be replaced by at least one Y 1 Substituted (C1-C6)-alkyl, (C1-C6)-alkoxy which may be substituted with at least one halogen, cyano or H, Y 1 is halogen, R 4 -C(=O)OR 5 、-C(=O)SR 6 、-C(=O)NR 7 R 8 , or -CH(OH)-C(=O)R 11 , R 7 can be represented by at least one Y 2 Substituted (C1-C6)-alkyl, H, or (C1-C6)-alkoxy, Z 1 is cyano, halogen, (C1-C6)-alkylthio, (C1-C6)-alkylsulfonyl, (C1-C6)-alkoxy, or 1,3-dioxolan-4-yl, R 6is a (C1-C6)-alkyl group which may be substituted with at least one halogen, R 7 can be represented by at least one Y 2 Substituted (C1-C6)-alkyl, H, or (C1-C6)-alkoxy, R 8 is H, or (C1-C6)-alkoxy, Y 2 is (C1-C6)-alkoxy, halogen, or cyano.

[0500]

[88] The difluorobutenamide compound or a salt thereof according to any one of

[85] to

[87] above, wherein m is 1 or 2.

[0501]

[89] The difluorobutenamide compound or a salt thereof according to any one of

[85] to

[88] above, wherein t is 1 and the carbon-carbon bond in the dotted line portion is a single bond.

[0502]

[90] The difluorobutenamide compound or a salt thereof according to any one of

[85] to

[88] above, wherein t is 2 and the carbon-carbon bond in the dotted line portion is a single bond.

[0503]

[91] A difluorobutenamide compound or a salt thereof as described in any one of

[85] to

[88] above, wherein t is 2, one of the carbon-carbon bonds in the dotted line portion is a single bond, and the other carbon-carbon bond in the dotted line portion is a double bond.

[0504]

[92] A herbicidal composition comprising the difluorocrotonamide compound or a salt thereof according to any one of [4] to

[91] above as an active ingredient.

[0505]

[93] A method for controlling undesirable plants or inhibiting their growth, wherein an effective amount of the difluorobutenamide compound or a salt thereof described in any one of [4] to

[92] above is applied to harmful weeds, useful plants, or soil.

[0506] Example

[0507] The present invention will be described in more detail below with reference to the examples, but the present invention should not be construed as being limited to the examples. First, the synthesis examples of the compounds of the present invention are described. 1 H-NMR spectral data were measured in the measurement solvent using JEOL JNM-ECX (500 MHz) or Bruker AVANCE III HD (300 MHz) ( 1 H-NMR spectroscopy). The assay solvent sometimes also contains tetramethylsilane (TMS) as an internal standard.

[0508] In this specification, room temperature refers to a temperature of about 10 to 35°C.

[0509] Synthesis example 1

[0510] Synthesis of (1RS,4SR)-4-[(E)-2,2-difluoro-4-(3-fluorophenyl)but-3-enoic acid amide]cyclopent-2-ene-1-carboxylic acid methyl ester (Compound No. Bb-3-1 described below)

[0511] (1) Synthesis of ethyl (E)-2,2-difluoro-4-(3-fluorophenyl)but-3-enoate

[0512] Under a nitrogen atmosphere, N1-[2-(dimethylamino)ethyl]-N1,N2,N2-trimethylethane-1,2-diamine (10.9 g) was added to a mixed solution of 1-fluoro-3-vinylbenzene (5.12 g), ethyl 2-bromo-2,2-difluoroacetate (12.76 g), copper (I) iodide (0.08 g) and acetonitrile (90 mL), and the mixture was reacted at 80°C for 14 hours to obtain a reaction mixture. The reaction mixture was cooled, water was added, and then extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The resulting residue was purified by column chromatography (eluent: heptane / ethyl acetate) to obtain yellow transparent liquid (E)-2,2-difluoro-4-(3-fluorophenyl)but-3-enoic acid ethyl ester (7.02 g, yield 69%).

[0513] 1 H NMR (500MHz, CDCl3): δppm=7.34(td,1H),7.21(d,1H),7.15(dt,1H),7.08-7.00(m,2H),6.30(dt,1H),4.35(q,2H),1.36(t,3H).

[0514] (2) Synthesis of (E)-2,2-difluoro-4-(3-fluorophenyl)but-3-enoic acid

[0515] A mixed solution of (E)-2,2-difluoro-4-(3-fluorophenyl)but-3-enoic acid ethyl ester (7.02g), tetrahydrofuran (40mL) and water (40mL) was cooled with water, and lithium hydroxide (4.13g) was added. The mixed solution was reacted at room temperature for 16.5 hours to obtain a reaction mixture. Tetrahydrofuran was distilled off from the above reaction mixture under reduced pressure to obtain a mixture. Water and 1M hydrochloric acid were added to the obtained mixture in sequence to make it acidic, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The residue obtained after distillation was placed at room temperature for 20 hours, and after crystals were generated, the above crystals were obtained by filtration and washed with n-heptane. Moreover, the solvent was distilled off from the filtrate under reduced pressure, and the obtained crystals were washed with n-heptane. The residue was combined with the previously obtained crystals to give (E)-2,2-difluoro-4-(3-fluorophenyl)but-3-enoic acid (4.85 g, yield 78%) as a white solid.

[0516] 1 H NMR (500MHz, CDCl3): δppm=7.46(br,1H), 7.35(td,1H), 7.22(d,1H), 7.15(dt,1H), 7.12-7.00(m,2H), 6.31(dt,1H).

[0517] (3) Synthesis of (1RS,4SR)-4-[(E)-2,2-difluoro-4-(3-fluorophenyl)but-3-enoic acid amide]cyclopent-2-ene-1-carboxylic acid methyl ester (Compound No. Bb-3-1 described below)

[0518] N,N-diisopropylethylamine (2.69 g) was added to a mixed solution of (E)-2,2-difluoro-4-(3-fluorophenyl)but-3-enoic acid (1.5 g), (1RS,4SR)-4-aminocyclopent-2-ene-1-carboxylic acid methyl ester hydrochloride (1.36 g), 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate (3.17 g) and N,N-dimethylformamide (15 mL), and the mixture was reacted at room temperature for 15 hours to obtain a mixed solution. Water was added to the mixed solution, and then extracted with ethyl acetate. The organic layer was washed with saturated brine, and the solvent was distilled off under reduced pressure. The obtained residue was purified by column chromatography (eluent: heptane / ethyl acetate) to obtain the target product as a light yellow solid (2.16 g, yield 92%).

[0519] 1H NMR(300MHz, CDCl3):7.32(dt,1H),7.22(d,1H),7.16-7.14(m,2H),7.06-7.01(m,2H),6.37(dt,1H),5. 99-5.97(m,1H),5.95-5.93(m,1H),5.09(t,1H),3.73(s,3H),3.55(d,1H),2.45(dt,1H),1.98(dt,1H).

[0520] Synthesis example 2

[0521] Synthesis of cis-3-[(E)-2,2-difluoro-4-(3-fluorophenyl)but-3-enoic acid amide]cyclobutane-1-carboxylic acid methyl ester (Compound No. Aa-3-1 described below)

[0522] N,N-diisopropylethylamine (0.24 g) was added to a mixed solution of (E)-2,2-difluoro-4-(3-fluorophenyl)but-3-enoic acid (0.1 g), cis-3-aminocyclobutane-1-carboxylic acid methyl ester hydrochloride (0.1 g), 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate (0.21 g) and N,N-dimethylformamide (2 mL), and the mixture was reacted at room temperature for 62.5 hours to obtain a mixed solution. Ethyl acetate was added to the mixed solution, and the organic layer was washed with saturated brine, and the solvent was distilled off under reduced pressure. The obtained residue was purified by column chromatography (eluent: heptane / ethyl acetate) to obtain the target product as a white solid (0.04 g, yield 26%).

[0523] 1 H NMR(300MHz, CDCl3):7.37-7.30(m,1H),7.22(d,1H),7.15(d,1H),7.08-6.99(m,2H),6.68(br,1H) ,6.35(dt,1H),4.45(sext,1H),3.71(s,3H),2.90(quin,1H),2.77-2.65(m,2H),2.29-2.17(m,2H).

[0524] Synthesis example 3

[0525] Synthesis of cis-3-[(E)-2,2-difluoro-4-(3,5-difluorophenyl)but-3-enoic acid amide]-N-methoxy-N-methylcyclobutane-1-carboxylic acid amide (Compound No. Aa-50-1 described below)

[0526] (1) Synthesis of cis-3-[(E)-2,2-difluoro-4-(3,5-difluorophenyl)but-3-enoic acid amide]cyclobutane-1-carboxylic acid

[0527] A mixed solution of cis-3-[(E)-2,2-difluoro-4-(3,5-difluorophenyl)but-3-enoic acid amide]cyclobutane-1-carboxylic acid methyl ester (0.40 g) and tetrahydrofuran (5 mL) was ice-cooled. An aqueous solution (5 mL) of lithium hydroxide (0.07 g) was added to the mixed solution under ice-cooling, and the mixture was reacted for 1 hour under ice-cooling to obtain a reaction mixture. After 1M hydrochloric acid was added to the reaction mixture to make it acidic, water was added, and tetrahydrofuran in the reaction mixture was distilled off under reduced pressure. After filtering the residue obtained after distillation to obtain crystals, the obtained crystals were dissolved in ethyl acetate, sodium sulfate was added and allowed to stand. Sodium sulfate was removed by filtration, and the filtrate was distilled off under reduced pressure. Cis-3-[(E)-2,2-difluoro-4-(3,5-difluorophenyl)but-3-enoic acid amide]cyclobutane-1-carboxylic acid (0.35 g, 91% yield) was obtained as a white solid.

[0528] 1 H NMR (300 MHz, acetone-d6): 10.64 (br, 0.44H), 8.30 (br, 1H), 7.42-7.28 (m, 2H), 7.18-7.00 (m, 2H), 6.69 (dt, 1H), 4.40 (sext, 1H), 2.99-2.85 (m, 1H), 2.65-2.52 (m, 2H), 2.42-2.25 (m, 2H). A peak of a proton of a carboxyl group was detected at 10.64 ppm.

[0529] (2) Synthesis of cis-3-[(E)-2,2-difluoro-4-(3,5-difluorophenyl)but-3-enoic acid amide]-N-methoxy-N-methylcyclobutane-1-carboxylic acid amide (Compound No. Aa-50-1 described below)

[0530] To a mixed solution of cis-3-[(E)-2,2-difluoro-4-(3,5-difluorophenyl)but-3-enoic acid amide]cyclobutane-1-carboxylic acid (0.15 g), N,O-dimethylhydroxylamine hydrochloride (0.05 g), triethylamine (0.11 g) and dichloromethane (5 mL), a 1.7 M ethyl acetate solution (0.36 mL) of propylphosphonic anhydride was added, and the mixture was reacted at room temperature for 1.5 hours to obtain a mixed solution. After adding water to the mixed solution, it was extracted with ethyl acetate. The organic layer was washed with saturated brine, and the solvent was distilled off under reduced pressure. The residue obtained after distillation was purified by column chromatography (eluent: heptane / ethyl acetate) to obtain the target product as a white solid (0.16 g, yield 92%).

[0531] 1 H NMR(300MHz, CDCl3):7.16-6.88(m,4H),6.78(tt,1H),6.36(dt,1H),4.47(sext, 1H),3.66(s,3H),3.31(t,1H),3.20(s,3H),2.72-2.58(m,2H),2.32-2.17(m,2H).

[0532] Synthesis example 4

[0533] Synthesis of ethyl 2-[3-{(E)-2,2-difluoro-4-(3,5-difluorophenyl)but-3-enoate amide}cyclobutylidene]acetate (Compound No. Aa-59 described below)

[0534] (1) Synthesis of (E)-[2,2-difluoro-4-(3,5-difluorophenyl)]-N-(3-oxocyclobutyl)but-3-enoic acid amide

[0535] Oxalyl chloride (0.26 g) was added to a mixed solution of (E)-2,2-difluoro-4-(3,5-difluorophenyl)but-3-enoic acid (0.4 g), N,N-dimethylformamide (3 drops were added with a Pasteur pipette), and tetrahydrofuran (4 mL), and the mixture was reacted at room temperature for 30 minutes to obtain a reaction solution A. Triethylamine (0.52 g) was added to a mixed solution of 3-aminocyclobutan-1-one hydrochloride (0.23 g) and tetrahydrofuran (6 mL) in another reaction container, and the mixture was cooled with ice to obtain a reaction solution B. After adding reaction solution A to reaction solution B under ice cooling, the mixture was reacted at room temperature for 1 hour to obtain a mixed solution. Water was added to the mixed solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and the solvent was distilled off under reduced pressure. The residue obtained after distillation was purified by column chromatography (eluent: heptane / ethyl acetate) to obtain (E)-[2,2-difluoro-4-(3,5-difluorophenyl)]-N-(3-oxocyclobutyl)but-3-enoic acid amide (0.46 g, yield 90%) as a white solid.

[0536] 1 H NMR (300MHz, CDCl3): δppm=7.05-6.93(m,3H),6.81(tt,1H),6.77(br,1H),6.38(dt,1H),4.61-4.49(m,1H),3.61-3.48(m,2H),3.25-3.13(m,2H).

[0537] (2) Synthesis of ethyl 2-[3-{(E)-2,2-difluoro-4-(3,5-difluorophenyl)but-3-enoate amide}cyclobutylidene]acetate (Compound No. Aa-59 described below)

[0538] A mixed solution of ethyl 2-diethoxyphosphonoacetate (0.16 g) and tetrahydrofuran (5 mL) was ice-cooled. Sodium hydride (0.03 g, purity 60%) was added to the mixed solution under ice-cooling, and stirred for 30 minutes under ice-cooling. After adding (E)-[2,2-difluoro-4-(3,5-difluorophenyl)]-N-(3-oxocyclobutyl)but-3-enoic acid amide (0.20 g) under ice-cooling, the mixture was reacted at room temperature for 1 hour to obtain a mixed solution. Ice water was added to the mixed solution, and then extracted with ethyl acetate. The organic layer was washed with saturated brine, and the solvent was distilled off under reduced pressure. The residue obtained after distillation was purified by column chromatography (eluent: heptane / ethyl acetate) to obtain the target product as a white solid (0.21 g, yield 85%).

[0539] 1 H NMR(300MHz, CDCl3):7.07-6.91(m,3H),6.80(tt,1H),6.63(br,1H),6.37(dt,1H),5.74(quin,1H),4.54(sex t,1H),4.16(q,2H),3.75-3.61(m,1H),3.38-3.25(m,1H),3.13-3.01(m,1H),2.92-2.80(m,1H),1.28(s,3H).

[0540] Next, the compounds listed below can be synthesized based on the above-mentioned production method and the above-mentioned synthesis example, as well as a method known in the technical field.

[0541] The No. in Table 1 indicates the No. of each substituent combination. 1 , R 2 , R 3 and (R 4 ) mThe abbreviations used in the columns represent the following substituents and the number of substituents, respectively. Me is methyl, Et is ethyl, CN is cyano, n-Pr is n-propyl, i-Pr is isopropyl, c-Pr is cyclopropyl, n-Bu is n-butyl, i-Bu is isobutyl, t-Bu is tert-butyl, n-Pent is n-pentyl, c-Pent is cyclopentyl, Ph is phenyl, 2-Py is 2-pyridyl, 3-Py is 3-pyridyl, 4-Py is 4-pyridyl, di is 2, tri is 3, and tetra is 4. In each column in Table 1, "-" is a single bond, "=" is a double bond, and "≡" is a triple bond. In addition, (R) in Table 1 is 4 ) m The numbers given to the chemical structural formulas in the column indicate R 4 The bonding position of , # indicates the bonding position.

[0542] The (R 4 ) m The positions of the substituents shown in the column represent the positions of the substituents in the chemical formulas described in Table 1. For example, in the case of the compound of formula (IAa), (R 4 ) m The compound described as "3-CO2Me" in the column is a compound having one R at the substitution position given in the following chemical formula: 4 The group is substituted with respect to cyclobutane. That is, it means that it is a compound of "m=1" in which only the 3-position of cyclobutane is substituted with CO2Me.

[0543] The compounds Aa-1 to Aa-287 of the present invention are compounds of formula (IAa):

[0544]

[0545] In the compound shown, R 1 , R 2 , R 3 and (R 4 ) m The combination is a compound of each combination (No. 1 to 287) described in Table 1. For example, the compound Aa-1 of the present invention refers to a compound represented by formula (IAa) wherein R 1 , R 2 , R 3 and (R 4 ) m The combination is the combination shown in No. 1 of Table 1 (R 1 =F, R 2 =F, R 3 =H、(R 4 )m=3-CO2Me), represents the compound shown in the following structure.

[0546]

[0547] Table 1

[0548]

[0549] Table 1 (continued)

[0550]

[0551] Table 1 (continued)

[0552]

[0553] Table 1 (continued)

[0554]

[0555] Table 1 (continued)

[0556]

[0557] Table 1 (continued)

[0558]

[0559] Table 1 (continued)

[0560]

[0561] Table 1 (continued)

[0562]

[0563] Table 1 (continued)

[0564]

[0565] Table 1 (continued)

[0566]

[0567] Table 1 (continued)

[0568]

[0569] Table 1 (continued)

[0570]

[0571] Table 1 (continued)

[0572]

[0573] The compounds Ab-1 to Ab-36, Ab-38 to Ab-58, Ab-60 to Ab-77, Ab-79 to Ab-155, Ab-158 to Ab-230 and Ab-232 to Ab-287 of the present invention are represented by the formula (IAb):

[0574]

[0575] In the compound shown, R 1 , R 2 , R 3 and (R 4 ) m The combinations are compounds of the combinations described in Table 1 (No. 1 to 36, No. 38 to 58, No. 60 to 77, No. 79 to 155, No. 158 to 230, and No. 232 to No. 287).

[0576] The compounds Ba-1 to Ba-287 of the present invention are represented by the compound of formula (IBa):

[0577]

[0578] In the compound shown, R 1 , R 2 , R 3 and (R 4 ) m The combinations are the compounds of the combinations described in Table 1 (No. 1 to 287).

[0579] The compounds Bb-1 to Ba-287 of the present invention are compounds of formula (IBb):

[0580]

[0581] In the compound shown, R 1 , R 2 , R 3 and (R 4 ) m The combinations are the compounds of the combinations described in Table 1 (No. 1 to 287).

[0582] The compounds Bc-1 to Bc-36, Bc-38 to Bc-58, Bc-60 to Bc-77, Bc-79 to Bc-155, Bc-158 to Bc-230 and Bc-232 to Bc-287 of the present invention are represented by the formula (IBc):

[0583]

[0584] In the compound shown, R 1 , R2 , R 3 and (R 4 ) m The combinations are compounds of the combinations described in Table 1 (No. 1 to 36, No. 38 to 58, No. 60 to 77, No. 79 to 155, No. 158 to 230, and No. 232 to No. 287).

[0585] The above-described compound of the present invention 1 The H-NMR data are shown in Table 2.

[0586] Comp No. in Table 2 indicates the compound number. In the remarks column, the difluorobutylene amide group and R substituted on the C4-C5 alicyclic hydrocarbon of the compound of the present invention are described. 4 It should be noted that the above-mentioned difluorobutyleneamide group refers to the part represented by the following chemical structural formula in the compound of the present invention (the symbols in the chemical structural formula are as described above).

[0587]

[0588] For example, if "cis" is written in the remarks column in Table 2, it means that the difluorobutylene amide group and R 4 If "trans" is written, it means that the difluorobutylene amide group and R 4 If it is written as "cis-trans", it means that the difluorobutylene amide group and R 4 The compound with cis configuration and difluorobutylene amide group and R 4 If it is described as "optically active form (1R, 4S)", it means that the difluorobutylene amide group is in R configuration, R 4 If it is described as "optically active form (1S, 4R)", it means that the difluorobutylene amide group is in the S configuration, R 4 It is an optically active form of R configuration. It should be noted that when there are two identical R4 at the same substitution position on the C4-C5 alicyclic hydrocarbon of the compound of the present invention and R 4 =CHC(=O)R 11 or =CHCH=CHC(=O)R 11 In the case of , "-" is written in the remarks column.

[0589] In addition, in compound (IAb), when the 2-position, 3-position, or both of the cyclobutenyl group have R4, "-" is recorded in the remarks column. However, in compound (IAb), when the difluorobutenamide group is in R configuration, it is recorded as R in the remarks column, and when the difluorobutenamide group is in S configuration, it is recorded as S in the remarks column.

[0590] In compound (IBb), when the difluorobutenoylamide group is in R configuration, it is described as R in the remarks column, and when the difluorobutenoylamide group is in S configuration, it is described as S in the remarks column.

[0591] When the 3-position, 4-position or both of the cyclopentenyl groups in the compound (IBc) have R4, "-" is recorded in the remarks column. However, in the compound (IBc), when the difluorobutenamide group is in R configuration, it is recorded as R in the remarks column, and when the difluorobutenamide group is in S configuration, it is recorded as S in the remarks column.

[0592] In Comp No. of Table 2, a branch number of 1 to 5 is added to the number of the above-mentioned compound of the present invention (e.g., Aa-1) to indicate the above-mentioned stereo configuration. The compound with branch number 1 added to Comp No., for example, "Aa-1-1", indicates that it is the compound Aa-1 of the present invention, and the difluorobutenoamide group and R4 are in cis configuration.

[0593] The compound with branch number 2 added to Comp No., for example, "Aa-1-2" means the compound Aa-1 of the present invention, and the difluorobutylene amide group and R 4 It is a trans-configuration compound.

[0594] The compound with branch number 3 added to Comp No., for example, "Aa-58-3" means the compound Aa-58 of the present invention, and the difluorobutylene amide group and R 4 It is a cis-configuration compound with difluorobutylene amide and R 4 It is a mixture of trans-configuration compounds.

[0595] For the compound with branch number 4 added in Comp No., for example, "Bb-1-4" means that it is the compound Bb-1 of the present invention, and the difluorobutenamide group is in S configuration, R 4 It is an optically active form of R configuration.

[0596] For the compound with branch number 5 added in Comp No., for example, "Bb-1-5" means that it is the compound Bb-1 of the present invention, and the difluorobuteneamide group is in R configuration, R 4 It is an optically active form of S configuration.

[0597] In Compound (IAb), Compound (IBb), and Compound (IBc), when the difluorobutenoylamide group is in R configuration, (R) is recorded after Comp No. For example, Bc-1(R) represents the compound Bc-1 of the present invention, in which the difluorobutenoylamide group is in R configuration.

[0598] Furthermore, in compound (IAb), compound (IBb) and compound (IBc), when the difluorobutenamide group is in S configuration, (S) is recorded after Comp No. For example, Bc-5(S) represents the compound Bc-5 of the present invention, in which the difluorobutenamide group is in S configuration.

[0599] In addition, when the compound of the present invention is a salt, the type of the salt is also recorded in the remarks column in Table 2. When the compound of the present invention is a salt, the type of the salt is recorded after Comp No. For example, Aa-48-1 (Na salt) means that it is the compound Aa-48 of the present invention, and the difluorobutylene amide group and R 4 It is the sodium salt of the compound with cis configuration.

[0600] Table 2 1 In the H-NMR data, s represents a singlet (single line), brs represents a broad singlet, br represents a broad peak (broad line), d represents a doublet (double line), brd represents a broad doublet, t represents a triplet (triplet), q represents a quartet (quadruple line), quin represents a quintet (quintet), sext represents a sextet (sextet), sep represents a septet (septet), and m represents a multiplet (multiple line).

[0601] Table 2

[0602]

[0603] Table 2 (continued)

[0604]

[0605] Table 2 (continued)

[0606]

[0607] Table 2 (continued)

[0608]

[0609] Table 2 (continued)

[0610]

[0611] Table 2 (continued)

[0612]

[0613] Table 2 (continued)

[0614]

[0615] Table 2 (continued)

[0616]

[0617] Table 2 (continued)

[0618]

[0619] Table 2 (continued)

[0620]

[0621] Table 2 (continued)

[0622]

[0623] Table 2 (continued)

[0624]

[0625] Table 2 (continued)

[0626]

[0627] Table 2 (continued)

[0628]

[0629] Table 2 (continued)

[0630]

[0631] Table 2 (continued)

[0632]

[0633] Table 2 (continued)

[0634]

[0635] Table 2 (continued)

[0636]

[0637] Table 2 (continued)

[0638]

[0639] Table 2 (continued)

[0640]

[0641] Table 2 (continued)

[0642]

[0643] Table 2 (continued)

[0644]

[0645] Table 2 (continued)

[0646]

[0647] Table 2 (continued)

[0648]

[0649] Table 2 (continued)

[0650]

[0651] Table 2 (continued)

[0652]

[0653] Table 2 (continued)

[0654]

[0655] Table 2 (continued)

[0656]

[0657] Table 2 (continued)

[0658]

[0659] Table 2 (continued)

[0660]

[0661] Table 2 (continued)

[0662]

[0663] Table 2 (continued)

[0664]

[0665] Table 2 (continued)

[0666]

[0667] Table 2 (continued)

[0668]

[0669] Table 2 (continued)

[0670]

[0671] Table 2 (continued)

[0672]

[0673] Table 2 (continued)

[0674]

[0675] Table 2 (continued)

[0676]

[0677] Table 2 (continued)

[0678]

[0679] Table 2 (continued)

[0680]

[0681] Table 2 (continued)

[0682]

[0683] Table 2 (continued)

[0684]

[0685] Table 2 (continued)

[0686]

[0687] Table 2 (continued)

[0688]

[0689] Table 2 (continued)

[0690]

[0691] Table 2 (continued)

[0692]

[0693] Table 2 (continued)

[0694]

[0695] Table 2 (continued)

[0696]

[0697] Table 2 (continued)

[0698]

[0699] Table 2 (continued)

[0700]

[0701] Table 2 (continued)

[0702]

[0703] Test Example 1: (1-1) Herbicidal effect on barnyard grass (stem and leaf treatment)

[0704] In a 1 / 300,000 hectare (ha) pot, dryland cultivation soil was placed, barnyardgrass (Echinochloa crus-galli) seeds were sown, and the soil was covered with about 1.5 cm. Then, it was cultivated in a greenhouse for 10 days until the specified leaf age was reached. The compound of the present invention was weighed in a manner to reach the specified amount of effective ingredient, and it was dissolved using acetone (containing 0.5 volume % of a surfactant (Triton X-100: manufactured by Kishida Chemical Co., Ltd.)) or dimethyl sulfoxide, and diluted in water equivalent to 1000 liters per hectare (containing 0.1 volume % of an agricultural spreading agent (Supafactant WK: manufactured by Maruwa Biochemical Co., Ltd.)) to prepare a spreading solution. After cultivation, the prepared spreading solution was treated with a small sprayer for stem and leaf treatment. After the treatment with the agent, the growth state of various plants was visually observed on the 14th day. As a result, each composition comprising the following compounds (each active ingredient amount was 125, 250, 500 or 1000 g / ha) showed a growth inhibition rate of 70% or more on barnyardgrass.

[0705] Compound (active ingredient amount: 1000g / ha): Comp No.Ba-3-1, Ba-19-1, Bb-3-1, Bb-8-1, Bb-19-1, Bb-20-1

[0706] Compound (active ingredient amount: 500 g / ha): Comp No.Aa-62-1, Aa-63-1, Aa-81-1, Ba-11-1, Ba-44-1, Ba-45-1, Ba-53-1, Ba-58-1, Bb-1-4, Bb-9-1, Bb-11-1, Bb-12-1, Bb-13-1, Bb-15-1, Bb-26-1, Bb-27-1, Bb-44-1, Bb-50-1, Bb-50-2, Bb-55-1, Bb-61-2, Bb-80-2, Bb-126-2, Bb-142-1, Bb-144-1, Bb-146-1, Bb-149-1, Bb-150-1, Bb-151-1, Bb-153-1, Bb-154-1, Bb-158-1, Bc-126

[0707] Compound (active ingredient amount: 250 g / ha): Comp No.Aa-1-1, Aa-3-1, Ba-1-1, Bb-1-1, Bb-46-3, Bb-48-1, Bb-79-3, Bb-114-3, Bb-123-3, Bb-133-3, Bb-134-3, Bb-135-3, Bb-75-3, Bb-136-3, Bb-72-3, Bb-163-3, Bb-164-3, Bb-165-3

[0708] Compound (active ingredient amount: 125 g / ha): Comp No. Aa-2-1, Aa-4-1, Aa-5-1, Aa-6-1, Aa-7-1, Aa-8-1, Aa-9-1, Aa-9-2, Aa-10-1, Aa-10-2, Aa-11-1, Aa-12-1, Aa-13-1, Aa-14-1, Aa-15-1, Aa-16-1, Aa-18-1, Aa-19-1, Aa-20-1, Aa-21-1, Aa-23-1, Aa-25-1, Aa-26-1, Aa-26-2, Aa-27-1, Aa-28-1, Aa-29-1, Aa-30-1, Aa-31-1, Aa-32-1, Aa-33-1, Aa-34-1, Aa-35-1, Aa-36-1, Aa-38-1, Aa-1-2, Aa-2-2, Aa-4-2, Aa-29-2, Aa-32-2, Aa-44-1, Aa-48-1, Aa-48-1 (Na salt), Aa-49-1, Aa-49-2, Aa-50-1, Aa-54-1, Aa-57-1, Aa-58-3, Aa-60-1, Aa-61-1, Aa-64-1, Aa-66-1, Aa-67-1, Aa-68-1, Aa-70-1, Aa-71-1, Aa-72-1, Aa-73-1, Aa-74-1, Aa-75-1, Aa-76-1, Aa-77-1, Aa-82-1, Aa-83-1, Aa-84-1, Aa-85-1, Aa-85-2, Aa-86-1, Aa-87-1, Aa-88-1, Aa-89-1, Aa-90-1, Aa-91-1, Aa-92-1, Aa-93-1, Aa-94-1, Aa-97-1, Aa-99-1, Aa-101-1, Aa-102-3, Aa-103-1, Aa-104-1, Aa-105-1, Aa-106-1, Aa-107-1, Aa-108-1, Aa-109-1, Aa-110-1, Aa-111-1, Aa-112-1, Aa-113-1, Aa-115-1, Aa-131-1, Aa-133-1, Aa-134-1·Aa-135-1, Aa-137-1, Aa-138-1, Aa-156-3, Aa-166-1, Aa-167-1, Aa-168-1, Aa-169-1, Aa-170-1, Aa-171-1, Aa-172-1, Aa-173-1, Aa-174-1, a-175-1, Aa-176-1, Aa-177-1, Aa-178-1, Aa-180-1, Aa-181-1, Aa-182-1, Aa-184-1,Aa-185-1, Aa-191-1, Aa-194-1, Aa-195-1, Aa-196-1, Aa-197-1, Aa-198-1, Aa-199-1, Aa-201-1, Aa-202-1, Aa-203-1, Aa-204-1, Aa-205-1, Aa-206-1, Aa-207-1, Aa-208-1, Aa-209-1, Aa-210-1, Aa-212-1, Aa-213-1, Aa-214-1, Aa-215-1, Aa-216-1 (HCl salt), Aa-217-1, Aa-218-1, Aa-219-3, Aa-220-2, Aa-220-3, Aa-221-3, Aa-222-3, Aa-223-2, Aa-223-3, Aa-224-3, Aa-225-3, Aa-226-1, Aa-226-2, Aa-227-1, Aa-228-2, Aa-229-2, Aa-230-3, Aa-232-3, Aa-233-1, Aa-234-1, Aa-235-1, Aa-236-1, Aa-238-1, Aa-240-1, Aa-241-1, Aa-242-1, Aa-243-1, Aa-244-1, Aa-246-1, Aa-247-1, Aa-248-1, Aa-249-1, Aa-250-3, Aa-253-1, Aa-254-1, Aa-255-1, Aa-256-1, Aa-257-1, Aa-257-2, Aa-258-1, Aa-259-1, Aa-259-2, Aa-260-1, Aa-261-2, Aa-262-1, Aa-262-2, Aa-263-1, Aa-264-1, Aa-265-1, Aa-265-2, Aa-263-2, Aa-267-1, Aa-272-1, Aa-272-2, Aa-273-2, Aa-277-2, Aa-278-2, Aa-279-2, Aa-280-2, Aa-281-2, Ba-1-2, Ba-64-1, Ba-76-1, Ba-119-1, Ba-223-1, Ba-226-1, Bb-1-2, Bb-1-5, Bb-2-1, Bb-5-1, Bb-5-5, Bb-7-1, Bb-45-1, Bb-49-1, Bb-49-2, Bb-60-1, Bb-60-2, Bb-64-1, Bb-71-3, Bb-73-1, Bb-76-1, Bb-77-3, Bb-102-1, Bb-119-1, Bb-124-1, Bb-127-1, Bb-128-1, Bb-130-1, Bb-131-1, Bb-132-1Bb-137-2, Bb-139-1, Bb-139-2, Bb-141-1, Bb-143-3, Bb-147-1, Bb-152-1, Bb-156-1, Bb-157-1, Bb-159-1, Bb-262-1, Bb-265-1, Bb-267- 1. Bc-1, Bc-1(R), Bc-1(S), Bc-3, Bc-5(R), Bc-44, Bc-48, Bc-49, Bc-53, Bc-60, Bc-72, Bc-73, Bc-127, Bc-129, Bc-223-1, Bc-262, Bc-265,

[0709] (1-2) Weed control effect on crabgrass (stem and leaf treatment)

[0710] In order to confirm the herbicidal effect on crabgrass (Digitaria sanguinalis), the following compounds were used and the same test method as in Test Example 1 (1-1) (stem and leaf treatment) was carried out. As a result, each composition containing the following compound (each active ingredient amount was 125, 250, 500 or 1000 g / ha) showed a growth inhibition rate of 70% or more on crabgrass.

[0711] Compound (active ingredient amount: 1000g / ha): Comp No.Ba-3-1, Ba-19-1, Bb-3-1, Bb-8-1, Bb-19-1, Bb-20-1

[0712] Compounds (active ingredient amount: 500g / ha): Comp.No.Aa-62-1, Ba-11-1, Ba-44-1, Ba-45-1, Ba-53-1, Ba-58-1, Bb-10-1, Bb-11-1, Bb-13-1, Bb-27-1, Bb-50-1, Bb-55-1, Bb-142-1, Bb-144-1, Bb-145-1, Bb-146-1, Bb-148-1, Bb-149-1, Bb-150-1, Bb-151-1, Bb-153-1, Bb-154-1, Bb-158-1, Bb-50-2

[0713] Compounds (active ingredient amount: 250 g / ha): Comp No. Aa-1-1, Aa-3-1, Ba-1-1, Bb-1-1, Bb-46-3, Bb-48-1, Bb-79-3, Bb-114-3, Bb-123-3, Bb-133-3, Bb-134-3, Bb-135-3, Bb-75-3, Bb-136-3, Bb-72-3, Bb-163-3, Bb-164-3, Bb-165-3

[0714] Compound (active ingredient amount: 125 g / ha): Comp No.Aa-2-1, Aa-4-1, Aa-5-1, Aa-6-1, Aa-7-1, Aa-8-1, Aa-9-1, Aa-9-2, Aa-10-1, Aa-10-2, Aa-11-1, Aa-14-1, Aa-15-1, Aa-16-1, Aa-18-1, Aa-19-1, Aa-20-1, Aa-21-1, Aa-25-1, Aa-26-2, Aa-27-1, Aa-28-1, Aa-29-1, Aa-30-1, Aa-31-1, Aa-32-1, Aa-33-1, Aa-34-1, Aa-36-1, Aa-38-1, Aa-1-2, Aa-2-2, Aa-4-2, Aa-29-2, Aa-32-2, Aa-22-2, Aa-23-2, Aa-44-1, Aa-45-1, Aa-47-1, Aa-48-1, Aa-49-1, Aa-49-2, Aa-50-1, Aa-53-1, Aa-54-1, Aa-57-1, Aa-66-1, Aa-67-1, Aa-71-1, Aa-72-1, Aa-73-1, Aa-75-1, Aa-76-1, Aa-82-1, Aa-83-1, Aa-84-1, Aa-85-1, Aa-85-2, Aa-86-1, Aa-87-1, Aa-88-1, Aa-89-1, Aa-90-1, Aa-91-1, Aa-92-1, Aa-93-1, Aa-94-1, Aa-95-1, Aa-96-1, Aa-97-1, Aa-99-1, Aa-100-1, Aa-102-3, Aa-103-1, Aa-104-1, Aa-105-1, Aa-106-1, Aa-107-1, Aa-108-1, Aa-109-1, Aa-110-1, Aa-111-1, Aa-112-1, Aa-113-1, Aa-115-1, Aa-131-1, Aa-48-1 (Na salt), Aa-133-1, Aa-134-1, Aa-135-1, Aa-137-1, Aa-138-1, Aa-156-3, Aa-166-1, Aa-167-1, Aa-168-1, Aa-169-1, Aa-170-1, Aa-172-1, Aa-173-1, Aa-174-1, Aa-175-1, Aa-177-1, Aa-178-1, Aa-179-1, Aa-180-1, Aa-181-1, Aa-182-1, Aa-184-1, Aa-185-1, Aa-209-1, Aa-210-1, Aa-211-1, Aa-212-1, Aa-213-1, Aa-214-1,Aa-215-1, Aa-216-1 (HCl salt), Aa-217-1, Aa-218-1, Aa-219-3, Aa-220-3, Aa-221-3, Aa-223-3, Aa-224-3, Aa-225-3, Aa-223-2, Aa-226-1, Aa-226-2, Aa-227-1, Aa-228-2, Aa-229-2, Aa-230-3, Aa-231, Aa-232-3, Aa-233-1, Aa-234-1, Aa-235-1, Aa-236-1, Aa-238-1, Aa-240-1, Aa-241-1, Aa-244-1, Aa-247-1, Aa-248-1, Aa-249-1, Aa-250-3, Aa-252-1, Aa-253-1, Aa-254-1, Aa-255-1, Aa-256-1, Aa-257-1, Aa-257-2, Aa-258-1, Aa-259-1, Aa-259-2, Aa-260-1, Aa-261-2, Aa-262-1, Aa-262-2, Aa-263-1, Aa-263-2, Aa-264-1, Aa-265-1, Aa-272-1, Aa-272-2, Aa-273-2, Aa-274-2, Aa-277-2, Aa-278-2, Aa-279-2, Aa-280-2, Aa-281-2, Ba-1-2, Ba-48-1, Ba-63-1, Ba-64-1, Ba-65-1, Ba-76-1, Ba-119-1, Ba-120-1, Ba-121-1, Ba-122-1, Ba-124-1, Ba-125-1, Ba-223-1, Ba-226-1, Bb-1-2, Bb-2-1, Bb-5-1, Bb-5-5, Bb-7-1, Bb-45-1, Bb-49-1, Bb-60-1, Bb-60-2, Bb-63-1, Bb-64-1, Bb-65-1, Bb-71-3, Bb-73-1, Bb-76-1, Bb-77-3, Bb-102-1, Bb-119-1, Bb-124-1, Bb-127-1, Bb-128-1, BB-130-1, Bb-1-5, Bb-137-1, Bb-138-1, Bb-139-1, Bb-143-3, Bb-147-1, Bb-152-1, Bb-155-1, Bb-156-1, Bb-157-1, Bb-159-1, Bb-160-1, Bb-161-1, Bb-162-1, Bb-49-2, Bb-137-2, Bb-138-2, Bb-262-1, Bb-265-1, Bb-267-1Bc-1, Bc-1(S), Bc-44, Bc-5(R), Bc-5, Bc-48, Bc-49, Bc-53, Bc-72, Bc-73, Bc-60, Bc-127, Bc-128, Bc-129, Bc-262, Bc-265,

[0715] (1-3) Weed control effect on Setaria viridis (stem and leaf treatment)

[0716] In order to confirm the herbicidal effect on green foxtail (Setaria viridis), the following compounds were used and the same test method as in Test Example 1 (1-1) (stem and leaf treatment) was implemented. The results showed that each composition containing the following compounds (each active ingredient amount was 125, 250, 500 or 1000 g / ha) showed a growth inhibition rate of 70% or more on green foxtail.

[0717] Compound (active ingredient amount: 1000g / ha): Comp No.Ba-3-1, Ba-19-1, Bb-3-1, Bb-8-1, Bb-19-1, Bb-20-1

[0718] Compound (active ingredient amount: 500g / ha): Comp No.Aa-52-1, Aa-63-1, Ba-11-1, Ba-44-1, Ba-45-1, Ba-53-1, Ba-58-1, Bb-10-1, Bb-13-1, Bb-44-1, Bb-50-1, Bb-55-1, Bb-80-2, Bb-142- 1. Bb-144-1, Bb-145-1, Bb-146-1, Bb-148-1, Bb-149-1, Bb-150-1, Bb-151-1, Bb-153-1, Bb-154-1, Bb-158-1, Bb-61-2, Bb-50-2, Bc-126

[0719] Compounds (active ingredient amount: 250 g / ha): Comp No. Aa-1-1, Aa-3-1, Ba-1-1, Bb-1-1, Bb-46-3, Bb-48-1, Bb-79-3, Bb-114-3, Bb-123-3, Bb-133-3, Bb-134-3, Bb-135-3, Bb-75-3, Bb-136-3, Bb-72-3, Bb-163-3, Bb-164-3, Bb-165-3

[0720] Compounds (active ingredient amount: 125 g / ha): Comp No. Aa-2-1, Aa-4-1, Aa-5-1, Aa-6-1, Aa-7-1, Aa-8-1, Aa-9-1, Aa-9-2, Aa-10-1, Aa-10-2, Aa-11-1, Aa-12-1, Aa-13-1, Aa-14-1, Aa-15-1, Aa-17-1, Aa-18-1, Aa-19-1, Aa-20-1, Aa-21-1, Aa-22-1, Aa-23-1, Aa-25-1, Aa-26-1, Aa-26-2, Aa-27-1, Aa-28-1, Aa-29-1, Aa-30-1, Aa-31-1, Aa-32-1, Aa-33-1, Aa-34-1, Aa-36-1, Aa-1-2, Aa-12-2, Aa-2-2, Aa-4-2, Aa-29-2, Aa-32-2, Aa-22-2, Aa-23-2, Aa-44-1, Aa-45-1, Aa-48-1, Aa-49-1, Aa-49-2, Aa-50-1, Aa-53-1, Aa-54-1, Aa-57-1, Aa-60-1, Aa-61-1, Aa-64-1, Aa-67-1, Aa-68-1, Aa-70-1, Aa-71-1, Aa-72-1, Aa-73-1, Aa-74-1, Aa-75-1, Aa-76-1, Aa-77-1, Aa-78, Aa-82-1, Aa-83-1, Aa-84-1, Aa-85-1, Aa-85-2, Aa-86-1, Aa-87-1, Aa-88-1, Aa-89-1, Aa-90-1, Aa-91-1, Aa-92-1, Aa-93-1, Aa-94-1, Aa-95-1, Aa-96-1, Aa-97-1, Aa-98-1, Aa-99-1, Aa-100-1, Aa-101-1, Aa-103-1, Aa-104-1, Aa-105-1, Aa-106-1, Aa-107-1, Aa-108-1, Aa-109-1, Aa-110-1, Aa-111-1, Aa-112-1, Aa-113-1, Aa-115-1, Aa-131-1, Aa-48-1 (Na salt), Aa-133-1, Aa-134-1, Aa-135-1, Aa-137-1, Aa-138-1, Aa-156-3, Aa-166-1, Aa-167-1, Aa-168-1, Aa-169-1, Aa-170-1, Aa-172-1, Aa-173-1, Aa-174-1, Aa-175-1, Aa-176-1, Aa-177-1, Aa-178-1,Aa-180-1, Aa-181-1, Aa-182-1, Aa-184-1, Aa-191-1, Aa-194-1, Aa-195-1, Aa-196-1, Aa-197-1, Aa-198-1, Aa-199-1, Aa-201-1, Aa-203-1, Aa-204-1, Aa-205-1, Aa-206-1, Aa-207-1, Aa-208-1, Aa-209-1, Aa-210-1, Aa-212-1, Aa-213-1, Aa-214-1, Aa-215-1, Aa-216-1 (HCl salt), Aa-217-1, Aa-220-3, Aa-221-3, Aa-223-3, Aa-224-3, Aa-225-3, Aa-223-2, Aa-220-2, Aa-226-1, Aa-226-2, Aa-227-1, Aa-228-2, Aa-229-2, Aa-230-3, Aa-231, Aa-232-3, Aa-233-1, Aa-234-1, Aa-235-1, Aa-236-1, Aa-238-1, Aa-240-1, Aa-241-1, Aa-242-1, Aa-243-1, Aa-244-1, Aa-247-1, Aa-248-1, Aa-249-1, Aa-250-3, Aa-253-1, Aa-254-1, Aa-255-1, Aa-257-1, Aa-257-2, Aa-258-1, Aa-259-1, Aa-259-2, Aa-260-1, Aa-261-2, Aa-262-1, Aa-262-2, Aa-263-1, Aa-263-2, Aa-264-1, Aa-265-1, Aa-265-2, Aa-267-1, Aa-267-2, Aa-272-1, Aa-272-2, Aa-273-2, Aa-277-2, Aa-278-2, Aa-279-2, Aa-280-2, Aa-281-2, Ba-1-2, Ba-63-1, Ba-64-1, Ba-76-1, Ba-119-1, Ba-120-1, Ba-121-1, Ba-122-1, Ba-223-1, Ba-226-1, Bb-1-2, Bb-2-1, Bb-5-5, Bb-7-1, Bb-45-1, Bb-49-1, Bb-60-1, Bb-60-2, Bb-63-1, Bb-64-1, Bb-71-3, Bb-73-1, Bb-76-1, Bb-77-3, Bb-102-1, Bb-119-1, Bb-124-1, Bb-127-1, Bb-128-1, Bb-1-5, Bb-137-1Bb-143-3, Bb-147-1, Bb-152-1, Bb-156-1, Bb-157-1, Bb-159-1, Bb-160-1, Bb-161-1, Bb-162-1, Bb-49-2, Bb-137-2, Bb-139-2, Bb-262-1, Bb-265-1, Bc-1, Bc-1(R), Bc-1(S), Bc-5(R), Bc-44, Bc-48, Bc-49, Bc -53, Bc-72, Bc-73, Bc-60, Bc-127, Bc-128, Bc-129, Bc-223-1, Bc-265,

[0721] (1-4) Weed control effect on oats (stem and leaf treatment)

[0722] In order to confirm the herbicidal effect on wild oat (Avena fatua), the following compounds were used and the same test method as in Test Example 1 (1-1) (stem and leaf treatment) was implemented. As a result, each composition containing the following compounds (each active ingredient amount was 125, 250, 500 or 1000 g / ha) showed a growth inhibition rate of 70% or more on wild oat.

[0723] Compound (active ingredient amount: 1000g / ha): Comp No.Ba-3-1, Ba-19-1, Bb-3-1, Bb-8-1, Bb-19-1, Bb-20-1

[0724] Compounds (active ingredient amount: 500g / ha): Comp No. Aa-42-1, Aa-43-1, Aa-52-1, Aa-55-1, Aa-62-1, Aa-63-1, Aa-81-1, Ba-11-1, Ba-44-1, Ba-53-1, Ba-58-1, Ba-116-3, Ba-117-3, Ba-118-3, Bb-9-1, Bb-10-1, Bb-11-1, Bb-12-1, Bb-13-1, Bb-15-1, Bb-26-1, Bb-27 -1, Bb-44-1, Bb-50-1, Bb-55-1, Bb-61-1, Bb-80-1, Bb-80-2, Bb-126-2, Bb-1-4, Bb-142-1, Bb-144-1, Bb-1 45-1, Bb-146-1, Bb-149-1, Bb-150-1, Bb-151-1, Bb-153-1, Bb-154-1, Bb-158-1, Bb-61-2, Bb-50-2, Bc-126

[0725] Compounds (active ingredient amount: 250 g / ha): Comp No. Aa-1-1, Aa-3-1, Ba-1-1, Bb-1-1, Bb-46-3, Bb-48-1, Bb-79-3, Bb-114-3, Bb-123-3, Bb-133-3, Bb-134-3, Bb-135-3, Bb-75-3, Bb-136-3, Bb-72-3, Bb-163-3, Bb-164-3, Bb-165-3

[0726] Compound (active ingredient amount: 125 g / ha): Comp No. Aa-2-1, Aa-4-1, Aa-5-1, Aa-6-1, Aa-7-1, Aa-8-1, Aa-9-1, Aa-9-2, Aa-10-1, Aa-10-2, Aa-11-1, Aa-12-1, Aa-13-1, Aa-14-1, Aa-15-1, Aa-16-1, Aa-17-1, Aa-18-1, Aa-19-1, Aa-20-1, Aa-21-1, Aa-22-1, Aa-23-1, Aa-24-1, Aa-25-1, Aa-26-1, Aa-26-2, Aa-27-1, Aa-28-1, Aa-29-1, Aa-30-1, Aa-31-1, Aa-32-1, Aa-33-1, Aa-34-1, Aa-35-1, Aa-36-1, Aa-37, Aa-38-1, Aa-39-1, Aa-40-1, Aa-41-1, Aa-1-2, Aa-12-2, Aa-2-2, Aa-4-2, Aa-29-2, Aa-32-2, Aa-22-2, Aa-23-2, Aa-44-1, Aa-45-1, Aa-47-1, Aa-48-1, Aa-49-1, Aa-49-2, Aa-50-1, Aa-53-1, Aa-54-1, Aa-56-1, Aa-57-1, Aa-58-3, Aa-59, Aa-60-1, Aa-61-1, Aa-64-1, Aa-65-1, Aa-66-1, Aa-67-1, Aa-68-1, Aa-69-1, Aa-70-1, Aa-71-1, Aa-72-1, Aa-73-1, Aa-74-1, Aa-75-1, Aa-76-1, Aa-77-1, Aa-78, Aa-82-1, Aa-83-1, Aa-84-1, Aa-85-1, Aa-85-2, Aa-86-1, Aa-87-1, Aa-88-1, Aa-89-1, Aa-90-1, Aa-91-1, Aa-92-1, Aa-93-1, Aa-94-1, Aa-95-1, Aa-96-1, Aa-97-1, Aa-99-1, Aa-100-1, Aa-101-1, Aa-102-3, Aa-103-1, Aa-103-2, Aa-104-1, Aa-105-1, Aa-106-1, Aa-107-1, Aa-108-1, Aa-109-1, Aa-110-1, Aa-111-1, Aa-112-1, Aa-113-1, Aa-115-1, Aa-131-1, Aa-48-1 (Na salt), Aa-133-1, Aa-134-1, Aa-135-1, Aa-137-1,Aa-138-1, Aa-156-3, Aa-166-1, Aa-167-1, Aa-168-1, Aa-169-1, Aa-170-1, Aa-171-1, Aa-172-1, Aa-173-1, Aa-174-1, Aa-175-1, Aa-176-1, Aa-177-1, Aa-178-1, Aa-179-1, Aa-180-1, Aa-181-1, Aa-182-1, Aa-183-1, Aa-184-1, Aa-185-1, Aa-186-1, Aa-187-1, Aa-188-1, Aa-189-1, Aa-190-1, Aa-191-1, Aa-192-1, Aa-193-1, Aa-194-1, Aa-195-1, Aa-196-1, Aa-197-1, Aa-198-1, Aa-199-1, Aa-200-1, Aa-201-1, Aa-202-1, Aa-203-1, Aa-204-1, Aa-205-1, Aa-206-1, Aa-207-1, Aa-208-1, Aa-209-1, Aa-210-1, Aa-211-1, Aa-212-1, Aa-213-1, Aa-214-1, Aa-215-1, Aa-216-1 (HCl salt), Aa-217-1, Aa-218-1, Aa-219-3, Aa-220-3, Aa-221-3, Aa-222-3, Aa-223-3, Aa-224-3, Aa-225-3, Aa-223-2, Aa-220-2, Aa-226-1, Aa-226-2, Aa-227-1, Aa-228-2, Aa-229-2, Aa-230-3, Aa-231, Aa-232-3, Aa-233-1, Aa-234-1, Aa-235-1, Aa-236-1, Aa-237-3, Aa-238-1, Aa-239-1, Aa-240-1, Aa-241-1, Aa-242-1, Aa-243-1, Aa-244-1, Aa-245-1, Aa-245-2, Aa-246-1, Aa-247-1, Aa-248-1, Aa-249-1, Aa-250-3, Aa-251-1, Aa-252-1, Aa-253-1, Aa-254-1, Aa-255-1, Aa-256-1, Aa-257-1, Aa-257-2, Aa-258-1, Aa-259-1, Aa-259-2, Aa-260-1, Aa-261-2, Aa-262-1, Aa-262-2, Aa-263-1, Aa-263-2, Aa-264-1, Aa-265-1Aa-265-2, Aa-266-1, Aa-267-1, Aa-267-2, Aa-268-1, Aa-269-1, Aa-270-2, Aa-271-1, Aa-271-2, Aa-272-1, Aa-272-2, Aa-273-2, Aa-274-1, Aa-274-2, Aa-275-2, Aa-275-1, Aa-276-1, Aa-277-1, Aa-277-2, Aa-278-2, Aa-279-2, Aa-280-2, Aa-281-2, Aa-282-2, Aa-283-2, Aa-284-2, Aa-285-2, Aa-286-2, Aa-287-1, Aa-287-2, Ba-9-1, Ba-1-2, Ba-63-1, Ba-64-1, Ba-65-1, Ba-76-1, Ba-119-1, Ba-120-1, Ba-121-1, Ba-122-1, Ba-125-1, Ba-223-1, Ba-226-1, Bb-1-2, Bb-2-1, Bb-5-1, Bb-5-5, Bb-7-1, Bb-45-1, Bb-49-1, Bb-53-1, Bb-60-1, Bb-60-2, Bb-71-3, Bb-73-1, Bb-76-1, Bb-77-3, Bb-102-1, Bb-119-1, Bb-127-1, Bb-128-1, BB-130-1, Bb-131-1, Bb-132-1, Bb-1-5, Bb-137-1, Bb-138-1, Bb-139-1, Bb-141-1, Bb-143-3, Bb-147-1, Bb-155-1, Bb-156-1, Bb-157-1, Bb-159-1, Bb-160-1, Bb-161-1, Bb-49-2, Bb-137-2, Bb-138-2, Bb-139-2, Bb-262-1, Bb-265-1, Bb-267-1, Bc-1, Bc-1(R), Bc-1(S), Bc-3, Bc-5(R), Bc-5, Bc-44, Bc-48, Bc-49, Bc-53, Bc-72, Bc-73, Bc-60, Bc-127, Bc-128, Bc-129, Bc-223-1, Bc-262, Bc-265, Bc-267

[0727] (1-5) Herbicidal effect on Lolium multiflorum (foliar treatment)

[0728] In order to confirm the herbicidal effect on Italian ryegrass (Lolium multiflorum), the following compounds were used and the same test method as in Test Example 1 (1-1) (stem and leaf treatment) was carried out. As a result, each composition containing the following compound (each active ingredient amount was 125, 250, 500 or 1000 g / ha) showed a growth inhibition rate of 70% or more on Italian ryegrass.

[0729] Compound (active ingredient amount: 1000g / ha): Comp No.Ba-3-1, Ba-19-1, Bb-3-1, Bb-8-1, Bb-19-1, Bb-20-1

[0730] Compounds (active ingredient amount: 500g / ha): Comp No. Aa-42-1, Aa-55-1, Aa-62-1, Aa-63-1, Ba-11-1, Ba-44-1, Ba-45-1, Ba-53-1, Ba-58-1, Ba-116-3, Ba-117-3, Ba-118-3, Bb-9-1, Bb-10-1, Bb-11-1, Bb-12-1, Bb-13-1, Bb-15-1, Bb-26-1, Bb-27-1, Bb-44 -1, Bb-50-1, Bb-55-1, Bb-61-1, Bb-80-1, Bb-80-2, Bb-126-2, Bb-1-4, Bb-142-1, Bb-144-1, Bb-145-1 , Bb-146-1, Bb-149-1, Bb-150-1, Bb-151-1, Bb-153-1, Bb-154-1, Bb-158-1, Bb-61-2, Bb-50-2, Bc-126

[0731] Compounds (active ingredient amount: 250 g / ha): Comp No. Aa-1-1, Aa-3-1, Ba-1-1, Bb-1-1, Bb-46-3, Bb-48-1, Bb-79-3, Bb-114-3, Bb-123-3, Bb-133-3, Bb-134-3, Bb-135-3, Bb-75-3, Bb-136-3, Bb-72-3, Bb-163-3, Bb-164-3, Bb-165-3

[0732] Compound (active ingredient amount: 125 g / ha): Comp No. Aa-2-1, Aa-4-1, Aa-5-1, Aa-6-1, Aa-7-1, Aa-8-1, Aa-9-1, Aa-9-2, Aa-10-1, Aa-10-2, Aa-11-1, Aa-12-1, Aa-13-1, Aa-14-1, Aa-15-1, Aa-16-1, Aa-17-1, Aa-18-1, Aa-19-1, Aa-20-1, Aa-21-1, Aa-22-1, Aa-23-1, Aa-25-1, Aa-26-1, Aa-26-2, Aa-27-1, Aa-28-1, Aa-29-1, Aa-30-1, Aa-31-1, Aa-32-1, Aa-33-1, Aa-34-1, Aa-35-1, Aa-36-1, Aa-38-1, Aa-39-1, Aa-40-1, Aa-41-1, Aa-1-2, Aa-12-2, Aa-2-2, Aa-4-2, Aa-29-2, Aa-32-2, Aa-22-2, Aa-23-2, Aa-44-1, Aa-45-1, Aa-48-1, Aa-49-1, Aa-49-2, Aa-50-1, Aa-51-1, Aa-53-1, Aa-54-1, Aa-56-1, Aa-57-1, Aa-58-3, Aa-59, Aa-60-1, Aa-61-1, Aa-64-1, Aa-65-1, Aa-66-1, Aa-67-1, Aa-68-1, Aa-70-1, Aa-71-1, Aa-72-1, Aa-73-1, Aa-74-1, Aa-75-1, Aa-76-1, Aa-77-1, Aa-78, Aa-82-1, Aa-83-1, Aa-84-1, Aa-85-1, Aa-85-2, Aa-86-1, Aa-87-1, Aa-88-1, Aa-89-1, Aa-90-1, Aa-91-1, Aa-92-1, Aa-93-1, Aa-94-1, Aa-95-1, Aa-96-1, Aa-97-1, Aa-99-1, Aa-100-1, Aa-101-1, Aa-102-3, Aa-103-1, Aa-103-2, Aa-104-1, Aa-105-1, Aa-106-1, Aa-107-1, Aa-108-1, Aa-109-1, Aa-110-1, Aa-111-1, Aa-112-1, Aa-113-1, Aa-115-1, Aa-131-1, Aa-48-1 (Na salt), Aa-133-1, Aa-134-1, Aa-135-1, Aa-137-1, Aa-138-1, Aa-156-3, Aa-166-1,Aa-167-1, Aa-168-1, Aa-169-1, Aa-170-1, Aa-172-1, Aa-173-1, Aa-174-1, Aa-175-1, Aa-176-1, Aa-177-1, Aa-178-1, Aa-179-1, Aa-180-1, Aa-181-1, Aa-182-1, Aa-184-1, Aa-185-1, Aa-186-1, Aa-190-1, Aa-191-1, Aa-192-1, Aa-193-1, Aa-194-1, Aa-195-1, Aa-196-1, Aa-197-1, Aa-198-1, Aa-199-1, Aa-200-1, Aa-201-1, Aa-202-1, Aa-203-1, Aa-204-1, Aa-205-1, Aa-206-1, Aa-207-1, Aa-208-1, Aa-209-1, Aa-210-1, Aa-211-1, Aa-212-1, Aa-213-1, Aa-214-1, Aa-215-1, Aa-216-1 (HCl salt), Aa-217-1, Aa-218-1, Aa-219-3, Aa-220-3, Aa-221-3, Aa-223-3, Aa-224-3, Aa-225-3, Aa-223-2, Aa-220-2, Aa-226-1, Aa-226-2, Aa-227-1, Aa-228-2, Aa-229-2, Aa-230-3, Aa-231, Aa-232-3, Aa-233-1, Aa-234-1, Aa-235-1, Aa-236-1, Aa-237-3, Aa-238-1, Aa-240-1, Aa-241-1, Aa-242-1, Aa-243-1, Aa-244-1, Aa-245-1, Aa-245-2, Aa-246-1, Aa-247-1, Aa-248-1, Aa-249-1, Aa-250-3, Aa-252-1, Aa-253-1, Aa-254-1, Aa-255-1, Aa-256-1, Aa-257-1, Aa-257-2, Aa-258-1, Aa-259-1, Aa-259-2, Aa-260-1, Aa-261-2, Aa-262-1, Aa-262-2, Aa-263-1, Aa-263-2, Aa-264-1, Aa-265-1, Aa-265-2, Aa-267-1, Aa-267-2, Aa-269-1, Aa-270-2, Aa-271-1, Aa-271-2, Aa-272-1, Aa-272-2, Aa-273-2, Aa-274-1Aa-274-2, Aa-275-2, Aa-275-1, Aa-276-1, Aa-276-2, Aa-277-1, Aa-277-2, Aa-278-2, Aa-279-2, Aa- 280-2, Aa-281-2, Aa-282-2, Aa-283-2, Aa-284-2, Aa-285-2, Aa-286-2, Ba-1-2, Ba-119-1, Ba-120-1 , Ba-122-1, Ba-223-1, Ba-226-1, Bb-1-2, Bb-2-1, Bb-5-1, Bb-5-5, Bb-7-1, Bb-45-1, Bb-49-1, Bb-53 -1, Bb-60-1, Bb-60-2, Bb-71-3, Bb-73-1, Bb-76-1, Bb-77-3, Bb-102-1, Bb-119-1, Bb-127-1, Bb-128- 1. BB-130-1, Bb-131-1, Bb-132-1, Bb-1-5, Bb-137-1, Bb-138-1, Bb-139-1, Bb-141-1, Bb-143-3, Bb- 147-1, Bb-152-1, Bb-156-1, Bb-157-1, Bb-159-1, Bb-160-1, Bb-161-1, Bb-49-2, Bb-137-2, Bb-138-2 , Bb-139-2, Bb-262-1, Bb-265-1, Bb-267-1, Bc-1, Bc-1(R), Bc-1(S), Bc-3, Bc-5(R), Bc-5, Bc-44, Bc -48, Bc-49, Bc-53, Bc-72, Bc-73, Bc-60, Bc-127, Bc-128, Bc-129, Bc-223-1, Bc-262, Bc-265, Bc-267,

[0733] (1-6) Weed control effect on Alopecurus mume (stem and leaf treatment)

[0734] In order to confirm the herbicidal effect on foxtail shortawn (Alopecurus aequalis), the following compounds were used and the same test method as in Test Example 1 (1-1) (stem and leaf treatment) was implemented. As a result, each composition containing the following compounds (each active ingredient amount was 125, 250, 500 or 1000 g / ha) showed a growth inhibition rate of more than 70% on foxtail shortawn.

[0735] Compound (active ingredient amount: 1000g / ha): Comp No.Ba-3-1, Ba-19-1, Bb-3-1, Bb-8-1, Bb-19-1, Bb-20-1

[0736] Compound (active ingredient amount: 500 g / ha): Comp No. Aa-42-1, Aa-52-1, Aa-55-1, Aa-62-1, Aa-63-1, Aa-81-1, Ba-11-1, Ba-44-1, Ba-45-1, Ba-53-1, Ba-58-1, Ba-116-3, Ba-117-3, Ba-118-3, Bb-9-1, Bb-10-1, Bb-11-1, Bb-12-1, Bb-13-1, Bb-15-1, Bb-26-1, Bb-27-1, Bb-44-1, Bb-50-1, Bb-55-1, Bb-61-1, Bb-80-1, Bb-80-2, Bb-126-2, Bb-1-4, Bb-142-1, Bb-144-1, Bb-145-1, Bb-146-1, Bb-148-1, Bb-149-1, Bb-150-1, Bb-151-1, Bb-153-1, Bb-154-1, Bb-158-1, Bb-61-2, Bb-50-2, Bc-126

[0737] Compound (active ingredient amount: 250 g / ha): Comp No. Aa-1-1, Aa-3-1, Ba-1-1, Bb-1-1, Bb-46-3, Bb-48-1, Bb-79-3, Bb-114-3, Bb-123-3, Bb-133-3, Bb-134-3, Bb-135-3, Bb-75-3, Bb-136-3, Bb-72-3, Bb-163-3, Bb-164-3, Bb-165-3

[0738] Compound (active ingredient amount: 125 g / ha): Comp No.Aa-2-1, Aa-4-1, Aa-5-1, Aa-6-1, Aa-7-1, Aa-8-1, Aa-9-1, Aa-9-2, Aa-10-1, Aa-10-2, Aa-11-1, Aa-12-1, Aa-13-1, Aa-14-1, Aa-15-1, Aa-16-1, Aa-17-1, Aa-18-1, Aa-19-1, Aa-20-1, Aa-21-1, Aa-22-1, Aa-23-1, Aa-24-1, Aa-25-1, Aa-26-1, Aa-26-2, Aa-27-1, Aa-28-1, Aa-29-1, Aa-30-1, Aa-31-1, Aa-32-1, Aa-33-1, Aa-34-1, Aa-35-1, Aa-36-1, Aa-38-1, Aa-39-1, Aa-40-1, Aa-41-1, Aa-1-2, Aa-12-2, Aa-2-2, Aa-4-2, Aa-29-2, Aa-32-2, Aa-22-2, Aa-23-2, Aa-44-1, Aa-45-1, Aa-47-1, Aa-48-1, Aa-49-1, Aa-49-2, Aa-50-1, Aa-51-1, Aa-53-1, Aa-54-1, Aa-56-1, Aa-57-1, Aa-58-3, Aa-59, Aa-60-1, Aa-61-1, Aa-64-1, Aa-65-1, Aa-66-1, Aa-67-1, Aa-68-1, Aa-69-1, Aa-70-1, Aa-71-1, Aa-72-1, Aa-73-1, Aa-74-1, Aa-75-1, Aa-77-1, Aa-78, Aa-82-1, Aa-83-1, Aa-84-1, Aa-85-1, Aa-85-2, Aa-86-1, Aa-87-1, Aa-88-1, Aa-100-1, Aa-101-1, Aa-102-3, Aa-103-1, Aa-103-2, Aa-104-1, Aa-105-1, Aa-106-1, Aa-107-1, Aa-108-1, Aa-109-1, Aa-110-1, Aa-111-1, Aa-112-1, Aa-113-1, Aa-115-1, Aa-131-1, Aa-48-1 (Na salt), Aa-133-1, Aa-134-1, Aa-135-1, Aa-137-1, Aa-138-1, Aa-156-3, Aa-166-1, Aa-167-1, Aa-168-1, Aa-169-1, Aa-170-1, Aa-171-1, Aa-172-1, Aa-173-1,Aa-174-1, Aa-175-1, Aa-176-1, Aa-177-1, Aa-178-1, Aa-179-1, Aa-180-1, Aa-181-1, Aa-182-1, Aa-183-1, Aa-184-1, Aa-185-1, Aa-186-1, Aa-187-1, Aa-188-1, Aa-189-1, Aa-190-1, Aa-191-1, Aa-192-1, Aa-193-1, Aa-194-1, Aa-195-1, Aa-196-1, Aa-197-1, Aa-198-1, Aa-199-1, Aa-200-1, Aa-201-1, Aa-202-1, Aa-203-1, Aa-204-1, Aa-205-1, Aa-206-1, Aa-207-1, Aa-208-1, Aa-209-1, Aa-210-1, Aa-211-1, Aa-212-1, Aa-213-1, Aa-214-1, Aa-215-1, Aa-216-1 (HCl salt), Aa-217-1, Aa-218-1, Aa-219-3, Aa-220-3, Aa-221-3, Aa-222-3, Aa-223-3, Aa-224-3, Aa-225-3, Aa-223-2, Aa-220-2, Aa-226-1, Aa-226-2, Aa-227-1, Aa-228-2, Aa-229-2, Aa-230-3, Aa-231, Aa-232-3, Aa-233-1, Aa-234-1, Aa-235-1, Aa-236-1, Aa-237-3, Aa-238-1, Aa-239-1, Aa-240-1, Aa-241-1, Aa-242-1, Aa-243-1, Aa-244-1, Aa-245-1, Aa-245-2, Aa-246-1, Aa-247-1, Aa-248-1, Aa-249-1, Aa-250-3, Aa-251-1, Aa-252-1, Aa-253-1, Aa-254-1, Aa-255-1, Aa-256-1, Aa-257-1, Aa-257-2, Aa-258-1, Aa-259-1, Aa-259-2, Aa-260-1, Aa-261-2, Aa-262-1, Aa-262-2, Aa-263-1, Aa-263-2, Aa-264-1, Aa-265-1, Aa-265-2, Aa-266-1, Aa-266-2, Aa-267-1, Aa-267-2, Aa-269-1, Aa-270-2, Aa-271-1, Aa-271-2, Aa-272-1Aa-272-2, Aa-273-2, Aa-274-1, Aa-274-2, Aa-275-2, Aa-275-1, Aa-276-1, Aa-276-2, Aa-277-1, Aa-277-2, Aa-278-2, Aa-279-2, Aa-280-2, Aa-281-2, Aa-282-2, Aa-283-2, Aa-284-2, Aa-285-2, Aa-286-2, Aa-287-1, Aa-287-2, Ba-9-1, Ba-1-2, Ba-63-1, Ba-64-1, Ba-65-1, Ba-76-1, Ba-119-1, Ba-120-1, Ba-121-1, Ba-122-1, Ba-223-1, Ba-226-1, Bb-1-2, Bb-2-1, Bb-5-1, Bb-5-5, Bb-7-1, Bb-45-1, Bb-49-1, Bb-53-1, Bb-60-1, Bb-60-2, Bb-63-1, Bb-64-1, Bb-65-1, Bb-71-3, Bb-73-1, Bb-76-1, Bb-77-3, Bb-102-1, Bb-119-1, Bb-124-1, Bb-127-1, Bb-128-1, BB-130-1, Bb-131-1, Bb-132-1, Bb-1-5, Bb-137-1, Bb-138-1, Bb-139-1, Bb-141-1, Bb-143-3, Bb-147-1, Bb-152-1, Bb-155-1, Bb-156-1, Bb-157-1, Bb-159-1, Bb-160-1, Bb-161-1, Bb-162-1, Bb-49-2, Bb-137-2, Bb-138-2, Bb-139-2, Bb-262-1, Bb-265-1, Bb-267-1, Bc-1, Bc-1(R), Bc-1(S), Bc-3, Bc-5(R), Bc-5, Bc-44, Bc-48, Bc-49, Bc-53, Bc-72, Bc-73, Bc-60, Bc-127, Bc-128, Bc-223-1, Bc-262, Bc-265, Bc-267,

[0739] (1-7) Herbicidal effect on Poa annua (foliar treatment)

[0740] In order to confirm the herbicidal effect on annual bluegrass (Poa annua), the following compounds were used and the same test method as in Test Example 1 (1-1) (stem and leaf treatment) was carried out. As a result, each composition containing the following compound (each active ingredient amount was 125, 250, 500, and 1000 g / ha) showed a growth inhibition rate of 70% or more on annual bluegrass.

[0741] Compound (active ingredient amount: 1000g / ha): Comp No. Bb-3-1, Bb-20-1

[0742] Compound (active ingredient amount: 500g / ha): Comp No.Aa-55-1, Aa-62-1, Aa-63-1, Ba-44-1, Ba-53-1, Ba-58-1, Ba-116-3, Ba-117-3, Bb-10-1, Bb-15-1, Bb-44-1, Bb-50-1, Bb-55-1, Bb-61-1, Bb-80 -2, Bb-126-2, Bb-1-4, Bb-142-1, Bb-145-1, Bb-146-1, Bb-149-1, Bb-150 -1, Bb-151-1, Bb-153-1, Bb-154-1, Bb-158-1, Bb-61-2, Bb-50-2, Bc-126

[0743] Compounds (active ingredient amount: 250 g / ha): Comp No. Aa-1, Aa-3-1, Bb-1-1, Bb-46-3, Bb-48-1, Bb-79-3, Bb-114-3, Bb-123-3, Bb-133-3, Bb-134-3, Bb-135-3, Bb-75-3, Bb-136-3, Bb-72-3, Bb-163-3, Bb-164-3, Bb-165-3

[0744] Compounds (active ingredient amount: 125 g / ha): Comp No. Aa-2-1, Aa-4-1, Aa-5-1, Aa-6-1, Aa-7-1, Aa-8-1, Aa-9-1, Aa-9-2, Aa-10-1, Aa-10-2, Aa-11-1, Aa-12-1, Aa-13-1, Aa-14-1, Aa-15-1, Aa-16-1, Aa-19-1, Aa-20-1, Aa-21-1, Aa-23-1, Aa-25-1, Aa-26-1, Aa-26-2, Aa-27-1, Aa-28-1, Aa-29-1, Aa-30-1, Aa-31-1, Aa-32-1, Aa-33-1, Aa-34-1, Aa-36-1, Aa-38-1, Aa-1-2, Aa-12-2, Aa-2-2, Aa-4-2, Aa-29-2, Aa-32-2, Aa-22-2, Aa-23-2, Aa-44-1, Aa-48-1, Aa-49-1, Aa-49-2, Aa-50-1, Aa-53-1, Aa-54-1, Aa-56-1, Aa-57-1, Aa-59, Aa-60-1, Aa-61-1, Aa-64-1, Aa-65-1, Aa-66-1, Aa-67-1, Aa-68-1, Aa-69-1, Aa-71-1, Aa-72-1, Aa-73-1, Aa-74-1, Aa-75-1, Aa-76-1, Aa-77-1, Aa-78, Aa-82-1, Aa-83-1, Aa-85-1, Aa-85-2, Aa-86-1, Aa-88-1, Aa-90-1, Aa-91-1, Aa-93-1, Aa-94-1, Aa-97-1, Aa-99-1, Aa-102-3, Aa-103-2, Aa-104-1, Aa-105-1, Aa-106-1, Aa-107-1, Aa-108-1, Aa-109-1, Aa-110-1, Aa-111-1, Aa-112-1, Aa-113-1, Aa-115-1, Aa-131-1, Aa-48-1Na (salt), Aa-133-1, Aa-134-1, Aa-135-1, Aa-137-1, Aa-138-1, Aa-156-3, Aa-166-1, Aa-167-1, Aa-168-1, Aa-169-1, Aa-170-1, Aa-171-1, Aa-172-1, Aa-173-1, Aa-174-1, Aa-175-1, Aa-176-1, Aa-177-1, Aa-178-1, Aa-179-1, Aa-180-1, Aa-181-1, Aa-182-1, Aa-183-1Aa-184-1、Aa-185-1、Aa-186-1、Aa-187-1、Aa-188-1、Aa-189-1、Aa-190-1 、Aa-191-1、Aa-192-1、Aa-193-1、Aa-194-1、Aa-195-1、Aa-196-1、Aa-197- 1、Aa-198-1、Aa-199-1、Aa-200-1、Aa-201-1、Aa-202-1、Aa-203-1、Aa-204 -1、Aa-205-1、Aa-206-1、Aa-207-1、Aa-208-1、Aa-215-1、Aa-217-1、Aa-218 -1、Aa-219-3、Aa-220-3、Aa-221-3、Aa-222-3、Aa-223-3、Aa-224-3、Aa-22 5-3、Aa-223-2、Aa-220-2、Aa-226-1、Aa-226-2、Aa-227-1、Aa-228-2、Aa-2 29-2、Aa-230-3、Aa-231、Aa-232-3、Aa-233-1、Aa-234-1、Aa-235-1、Aa-23 6-1、Aa-237-3、Aa-238-1、Aa-239-1、Aa-240-1、Aa-241-1、Aa-242-1、Aa-24 3-1、Aa-244-1、Aa-245-1、Aa-245-2、Aa-246-1、Aa-247-1、Aa-248-1、Aa-2 49-1、Aa-250-3、Aa-251-1、Aa-252-1、Aa-253-1、Aa-254-1、Aa-255-1、Aa- 256-1、Aa-257-1、Aa-257-2、Aa-258-1、Aa-259-1、Aa-259-2、Aa-260-1、Aa -261-2、Aa-262-1、Aa-262-2、Aa-263-1、Aa-263-2、Aa-264-1、Aa-265-1、Aa -265-2、Aa-266-1、Aa-266-2、Aa-267-1、Aa-267-2、Aa-269-1、Aa-270-2、A a-271-1、Aa-271-2、Aa-272-1、Aa-272-2、Aa-273-2、Aa-274-1、Aa-274-2、A a-275-2、Aa-275-1、Aa-276-1、Aa-276-2、Aa-277-1、Aa-277-2、Aa-278-2、 Aa-279-2、Aa-280-2、Aa-281-2、Aa-282-2、Aa-283-2、Aa-284-2、Aa-285-2、Aa-286-2, Ba-1-2, Ba-64-1, Ba-119-1, Ba-120-1, Ba-121-1, Ba-122-1, Ba-223-1, Ba-226-1, Bb-1-2, Bb-2-1, Bb-5-1, Bb-5-5, Bb-7-1, Bb-45- 1. Bb-49-1, Bb-53-1, Bb-60-1, Bb-60-2, Bb-71-3, Bb-73-1, Bb-76-1, Bb -77-3, Bb-102-1, Bb-119-1, Bb-127-1, Bb-130-1, Bb-131-1, Bb-1-5, Bb -137-1, Bb-138-1, Bb-139-1, Bb-143-3, Bb-152-1, Bb-156-1, Bb-159- 1. Bb-161-1, Bb-49-2, Bb-137-2, Bb-138-2, Bb-139-2, Bb-262-1, Bb-26 5-1, Bb-267-1, Bc-1, Bc-1(R), Bc-1(S), Bc-3, Bc-5(R), Bc-5, Bc-48, Bc -72, Bc-73, Bc-60, Bc-127, Bc-129, Bc-223-1, Bc-262, Bc-265, Bc-267,

[0745] (1-8) Herbicidal effect on Amaranthus retroflexus (stem and leaf treatment)

[0746] In order to confirm the herbicidal effect on redroot pigweed (Amaranthus retroflexus), the following compounds were used and the same test method as in Test Example 1 (1-1) (stem and leaf treatment) was implemented. As a result, each composition containing the following compound (each active ingredient amount was 125, 250, 500, and 1000 g / ha) showed a growth inhibition rate of 70% or more on redroot pigweed.

[0747] Compound (active ingredient amount: 1000g / ha): Comp No.Ba-3-1, Ba-19-1, Bb-3-1, Bb-8-1, Bb-19-1, Bb-20-1

[0748] Compounds (active ingredient amount: 500g / ha): Comp No. Aa-62-1, Aa-63-1, Ba-11-1, Bb-10-1, Bb-11-1, Bb-13-1, Bb-44-1, Bb-50-1, Bb-80-2, Bb-142-1, Bb-144-1, Bb-145-1, Bb-146-1, Bb-149-1, Bb-150-1, Bb-151-1, Bb-158-1, Bb-61-2, Bc-126

[0749] Compounds (active ingredient amount: 250 g / ha): Comp No. Aa-1-1, Aa-3-1, Ba-1-1, Bb-1-1, Bb-46-3, Bb-48-1, Bb-79-3, Bb-114-3, Bb-123-3, Bb-133-3, Bb-134-3, Bb-135-3, Bb-75-3, Bb-136-3, Bb-72-3, Bb-163-3, Bb-164-3, Bb-165-3

[0750] Compound (active ingredient amount: 125 g / ha): Comp No. Aa-2-1, Aa-4-1, Aa-5-1, Aa-7-1, Aa-10-1, Aa-10-2, Aa-19-1, Aa-21-1, Aa-26-1, Aa-28-1, Aa-29-1, Aa-34-1, Aa-29-2, Aa-44-1, Aa-49-2, Aa-50-1, Aa-57-1, Aa-61-1, Aa-72-1, Aa-78, Aa-102-3, Aa-131-1, Aa-48-1 (Na salt), Aa-133-1, Aa-134-1, Aa-135-1, Aa-137-1, Aa-138-1, Aa-166-1, Aa-167-1, Aa-168-1, Aa-172-1, Aa-173-1, Aa-174-1, Aa-176-1, Aa-177-1, Aa-178-1, Aa-181-1, Aa-182-1, Aa-207-1, Aa-217-1, Aa-220-3, Aa-223-3, Aa-225-3, Aa-223-2, Aa-226-1, Aa-226-2, Aa-230-3, Aa-233-1, Aa-234-1, Aa-235-1, Aa-236-1, Aa-240-1, Aa-246-1, Aa-247-1, Aa-254-1, Aa-263-1, Aa-264-1, Aa-271-2, Ba-1-2, Ba-223-1, Bb-1-2, Bb-2-1, Bb-5-1, Bb-5-5, Bb-7-1, Bb-49-1, Bb-60-1, Bb-60-2, Bb-71-3, Bb-73-1, Bb-77-3, Bb-102-1, Bb-127-1, Bb-128-1, Bb-131-1, Bb-1-5, Bb-137-1, Bb-139-1, Bb-143-3, Bb-152-1, Bb-156-1, Bb-157-1, Bb-161-1, Bb-49-2, Bb-137-2, Bb-138-2, Bb-139-2, Bb-262-1, Bb-265-1, Bc-1(S), Bc-5(R), Bc-49, Bc-53, Bc-72, Bc-60, Bc-127, Bc-128, Bc-262, Bc-265

[0751] (1-9) Weeding effect on Stellaria media (foliar treatment)

[0752] In order to confirm the herbicidal effect on common chickweed (Stellaria media), the following compounds were used and the same test method as in Test Example 1 (1-1) (stem and leaf treatment) was carried out. As a result, each composition containing the following compound (each active ingredient amount was 125, 250, 500 or 1000 g / ha) showed a growth inhibition rate of 70% or more on common chickweed.

[0753] Compound (active ingredient amount: 1000g / ha): Comp No.Ba-3-1, Ba-19-1, Bb-3-1, Bb-8-1, Bb-19-1, Bb-20-1

[0754] Compounds (active ingredient amount: 500g / ha): Comp No. Aa-52-1, Aa-55-1, Aa-62-1, Aa-63-1, Aa-81-1, Ba-11-1, Ba-44-1, Ba-45-1, Ba-53-1, Ba-58-1, Ba-116-3, Ba-117-3, Ba-118-3, Bb-9-1, Bb-10-1, Bb-11-1, Bb-12-1, Bb-13-1, Bb-15-1, Bb-26-1, Bb-27-1, Bb-44- 1. Bb-50-1, Bb-55-1, Bb-61-1, Bb-80-1, Bb-80-2, Bb-126-2, Bb-1-4, Bb-142-1, Bb-144-1, Bb-145-1, Bb-1 46-1, Bb-148-1, Bb-149-1, Bb-150-1, Bb-151-1, Bb-153-1, Bb-154-1, Bb-158-1, Bb-61-2, Bb-50-2, Bc-126

[0755] Compounds (active ingredient amount: 250 g / ha): Comp No. Aa-1-1, Aa-3-1, Ba-1-1, Bb-1-1, Bb-46-3, Bb-48-1, Bb-79-3, Bb-114-3, Bb-123-3, Bb-133-3, Bb-134-3, Bb-135-3, Bb-75-3, Bb-136-3, Bb-72-3, Bb-163-3, Bb-164-3, Bb-165-3

[0756] Compound (active ingredient amount: 125 g / ha): Comp No. Aa-2-1, Aa-4-1, Aa-5-1, Aa-6-1, Aa-7-1, Aa-8-1, Aa-9-1, Aa-9-2, Aa-10-1, Aa-10-2, Aa-11-1, Aa-12-1, Aa-13-1, Aa-14-1, Aa-15-1, Aa-16-1, Aa-18-1, Aa-19-1, Aa-20-1, Aa-21-1, Aa-22-1, Aa-23-1, Aa-25-1, Aa-26-1, Aa-27-1, Aa-28-1, Aa-29-1, Aa-30-1, Aa-31-1, Aa-32-1, Aa-33-1, Aa-34-1, Aa-35-1, Aa-36-1, Aa-38-1, Aa-39-1, Aa-1-2, Aa-2-2, Aa-32-2, Aa-22-2, Aa-23-2, Aa-44-1, Aa-45-1, Aa-48-1, Aa-49-1, Aa-49-2, Aa-50-1, Aa-51-1, Aa-53-1, Aa-54-1, Aa-56-1, Aa-57-1, Aa-58-3, Aa-59, Aa-60-1, Aa-61-1, Aa-64-1, Aa-65-1, Aa-66-1, Aa-67-1, Aa-68-1, Aa-70-1, Aa-71-1, Aa-72-1, Aa-73-1, Aa-74-1, Aa-75-1, Aa-76-1, Aa-77-1, Aa-78, Aa-82-1, Aa-83-1, Aa-84-1, Aa-85-1, Aa-85-2, Aa-86-1, Aa-87-1, Aa-88-1, Aa-89-1, Aa-90-1, Aa-91-1, Aa-92-1, Aa-93-1, Aa-94-1, Aa-95-1, Aa-96-1, Aa-97-1, Aa-98-1, Aa-99-1, Aa-101-1, Aa-102-3, Aa-103-1, Aa-104-1, Aa-105-1, Aa-106-1, Aa-107-1, Aa-108-1, Aa-109-1, Aa-110-1, Aa-111-1, Aa-112-1, Aa-113-1, Aa-115-1, Aa-131-1, Aa-48-1 (Na salt), Aa-133-1, Aa-134-1, Aa-135-1, Aa-137-1, Aa-138-1, Aa-156-3, Aa-166-1, Aa-167-1, Aa-168-1, Aa-169-1, Aa-170-1, Aa-172-1, Aa-173-1, Aa-174-1,Aa-175-1, Aa-176-1, Aa-177-1, Aa-178-1, Aa-180-1, Aa-181-1, Aa-182-1, Aa-183-1, Aa-184-1, Aa-185-1, Aa-187-1, Aa-188-1, Aa-190-1, Aa-191-1, Aa-192-1, Aa-193-1, Aa-194-1, Aa-195-1, Aa-196-1, Aa-197-1, Aa-198-1, Aa-199-1, Aa-200-1, Aa-201-1, Aa-202-1, Aa-203-1, Aa-204-1, Aa-205-1, Aa-206-1, Aa-207-1, Aa-208-1, Aa-209-1, Aa-210-1, Aa-212-1, Aa-213-1, Aa-214-1, Aa-215-1, Aa-216-1 (HCl salt), Aa-217-1, Aa-219-3, Aa-220-3, Aa-221-3, Aa-222-3, Aa-223-3, Aa-224-3, Aa-225-3, Aa-223-2, Aa-220-2, Aa-226-1, Aa-226-2, Aa-227-1, Aa-228-2, Aa-229-2, Aa-231, Aa-232-3, Aa-233-1, Aa-234-1, Aa-235-1, Aa-236-1, Aa-238-1, Aa-239-1, Aa-240-1, Aa-241-1, Aa-242-1, Aa-243-1, Aa-244-1, Aa-247-1, Aa-248-1, Aa-249-1, Aa-250-3, Aa-254-1, Aa-255-1, Aa-257-1, Aa-257-2, Aa-258-1, Aa-259-1, Aa-260-1, Aa-261-2, Aa-262-1, Aa-263-1, Aa-263-2, Aa-264-1, Aa-267-1, Aa-272-1, Aa-272-2, Aa-273-2, Aa-278-2, Aa-278-2, Aa-279-2, Aa-281-2, Ba-9-1, Ba-1-2, Ba-64-1, Ba-65-1, Ba-76-1, Ba-119-1, Ba-120-1, Ba-121-1, Ba-122-1, Ba-124-1, Ba-125-1, Ba-223-1, Ba-226-1, Bb-1-2, Bb-2-1, Bb-5-1, Bb-5-5, Bb-7-1, Bb-45-1, Bb-49-1, Bb-53-1, Bb-60-1, Bb-60-2Bb-63-1, Bb-64-1, Bb-65-1, Bb-73-1, Bb-76-1, Bb-77-3, Bb-102-1, Bb-119-1, Bb-124-1, Bb-127-1, Bb-128-1, BB-130-1, Bb-131- 1. Bb-132-1, Bb-1-5, Bb-137-1, Bb-138-1, Bb-139-1, Bb-141-1, Bb-143-3, Bb-147-1, Bb-152-1, Bb-155-1, Bb-156-1, Bb-157-1, Bb -159-1, Bb-160-1, Bb-161-1, Bb-162-1, Bb-49-2, Bb-137-2, Bb-138-2, Bb-139-2, Bb-262-1, Bb-265-1, Bb-267-1, Bc-1, Bc-1(R), Bc-1(S), Bc-3, Bc-5(R), Bc-5, Bc-44, Bc-48, Bc-49, Bc-53, Bc-72, Bc-73, Bc-60, Bc-127, Bc-128, Bc-129, Bc-262, Bc-265, Bc-267,

[0757] (1-10) Herbicidal effect on velvetleaf (stem and leaf treatment)

[0758] In order to confirm the herbicidal effect on velvetleaf (Abutilon theophrasti), the following compounds were used and the same test method as in Test Example 1 (1-1) (stem and leaf treatment) was carried out. As a result, each composition containing the following compound (each active ingredient amount was 125, 250, 500 or 1000 g / ha) showed a growth inhibition rate of 70% or more on velvetleaf.

[0759] Compound (active ingredient amount: 1000g / ha): Comp No. Ba-19-1, Bb-3-1, Bb-8-1, Bb-19-1, Bb-20-1

[0760] Compounds (active ingredient amount: 500g / ha): Comp No. Aa-62-1, Aa-63-1, Aa-81-1, Ba-11-1, Ba-45-1, Bb-9-1, Bb-10-1, Bb-11-1, Bb-12-1, Bb-13-1, Bb-15-1, Bb-27-1, Bb-44-1, Bb-50-1, Bb-55-1, Bb-142-1, Bb-144-1, Bb-145-1, Bb-146-1, Bb-150-1, Bb-151-1, Bb-153-1, Bb-154-1, Bb-158-1

[0761] Compounds (active ingredient amount: 250 g / ha): Comp No. Bb-1-1, Bb-46-3, Bb-48-1, Bb-79-3, Bb-123-3, Bb-133-3, Bb-134-3, Bb-135-3, Bb-75-3, Bb-136-3, Bb-72-3, Bb-163-3, Bb-164-3, Bb-165-3

[0762] Compound (active ingredient amount: 125g / ha): Comp No.Aa-4-1, Aa-8-1, Aa-9-1, Aa-10-1, Aa-14-1, Aa-27-1, Aa-28-1, Aa- 34-1, Aa-67-1, Aa-86-1, Aa-88-1, Aa-91-1, Aa-93-1, Aa-94-1, Aa-96-1 , Aa-97-1, Aa-99-1, Aa-178-1, Aa-180-1, Aa-219-3, Aa-254-1, Ba-64-1 , Ba-65-1, Ba-119-1, Ba-124-1, Bb-2-1, Bb-5-1, Bb-7-1, Bb-45-1, Bb-4 9-1, Bb-60-1, Bb-63-1, Bb-64-1, Bb-65-1, Bb-71-3, Bb-73-1, Bb-76-1, Bb-77-3, Bb-119-1, Bb-124-1, Bb-127-1, Bb-128-1, BB-130-1, Bb-131- 1. Bb-132-1, Bb-1-5, Bb-138-1, Bb-143-3, Bb-152-1, Bb-156-1, Bb-157 -1, Bb-162-1, Bb-262-1, Bb-265-1, Bb-267-1, Bc-1(S), Bc-129, Bc-265

[0763] (1-11) Herbicidal effect on Chenopodium album (stem and leaf treatment)

[0764] In order to confirm the herbicidal effect on common lambsquarters (Chenoqodium album), the following compounds were used and the same test method as in Test Example 1 (1-1) (stem and leaf treatment) was carried out. As a result, each composition containing the following compound (each active ingredient amount was 125, 250, 500 or 1000 g / ha) showed a growth inhibition rate of 70% or more on Chenoqodium.

[0765] Compound (active ingredient amount: 1000g / ha): Comp No. Ba-19-1, Bb-3-1, Bb-8-1, Bb-19-1, Bb-20-1

[0766] Compounds (active ingredient amount: 500g / ha): Comp No. Aa-52-1, Aa-62-1, Aa-63-1, Aa-81-1, Ba-11-1, Ba-58-1, Ba-116-3, Ba-117-3, Bb-9-1, Bb-10-1, Bb-11-1, Bb-12-1, Bb-13-1, Bb-15-1, Bb-26-1, Bb-27-1, Bb-44-1, Bb-50-1, Bb -61-1, Bb-80-1, Bb-80-2, Bb-1-4, Bb-142-1, Bb-144-1, Bb-145-1, Bb-146-1, Bb-148-1, B b-149-1, Bb-150-1, Bb-151-1, Bb-153-1, Bb-154-1, Bb-158-1, Bb-61-2, Bb-50-2, Bc-126

[0767] Compounds (active ingredient amount: 250 g / ha): Comp No. Aa-1-1, Aa-3-1, Ba-1-1, Bb-1-1, Bb-46-3, Bb-48-1, Bb-79-3, Bb-114-3, Bb-123-3, Bb-133-3, Bb-134-3, Bb-135-3, Bb-75-3, Bb-136-3, Bb-72-3, Bb-163-3, Bb-164-3, Bb-165-3

[0768] Compound (active ingredient amount: 125 g / ha): Comp No. Aa-4-1, Aa-5-1, Aa-6-1, Aa-7-1, Aa-8-1, Aa-9-1, Aa-9-2, Aa-10-1, Aa-10-2, Aa-11-1, Aa-12-1, Aa-13-1, Aa-14-1, Aa-15-1, Aa-16-1, Aa-18-1, Aa-19-1, Aa-20-1, Aa-21-1, Aa-25-1, Aa-27-1, Aa-28-1, Aa-29-1, Aa-32-1, Aa-33-1, Aa-34-1, Aa-35-1, Aa-12-2, Aa-22-2, Aa-44-1, Aa-48-1, Aa-49-1, Aa-49-2, Aa-50-1, Aa-56-1, Aa-57-1, Aa-59, Aa-60-1, Aa-61-1, Aa-64-1, Aa-65-1, Aa-66-1, Aa-67-1, Aa-68-1, Aa-71-1, Aa-72-1, Aa-73-1, Aa-76-1, Aa-78, Aa-82-1, Aa-85-2, Aa-88-1, Aa-89-1, Aa-102-3, Aa-103-1, Aa-104-1, Aa-107-1, Aa-108-1, Aa-109-1, Aa-110-1, Aa-115-1, Aa-131-1, Aa-48-1 (Na salt), Aa-134-1, Aa-135-1, Aa-137-1, Aa-138-1, Aa-166-1, Aa-170-1, Aa-172-1, Aa-174-1, Aa-176-1, Aa-177-1, Aa-178-1, Aa-180-1, Aa-182-1, Aa-183-1, Aa-184-1, Aa-185-1, Aa-191-1, Aa-192-1, Aa-194-1, Aa-195-1, Aa-196-1, Aa-197-1, Aa-198-1, Aa-199-1, Aa-201-1, Aa-203-1, Aa-205-1, Aa-206-1, Aa-207-1, Aa-208-1, Aa-210-1, Aa-212-1, Aa-214-1, Aa-215-1, Aa-219-3, Aa-220-3, Aa-221-3, Aa-222-3, Aa-223-3, Aa-225-3, Aa-223-2, Aa-220-2, Aa-226-1, Aa-226-2, Aa-227-1, Aa-228-2, Aa-229-2, Aa-231, Aa-232-3, Aa-233-1, Aa-234-1, Aa-240-1,Aa-242-1, Aa-243-1, Aa-244-1, Aa-249-1, Aa-250-3, Aa-254-1, Aa-255-1, Aa-257-1, Aa-257-2, Aa-258-1, Aa-260-1, Aa-261-2, Aa-263-2, Aa-264-1, Aa-265-1, Aa-272-2, Aa-273-2, Aa-277-2, Aa-281-2, Ba-9-1, Ba-1-2, Ba-64-1, Ba-76-1, Ba-124-1, Ba-125 -1, Bb-1-2, Bb-2-1, Bb-5-1, Bb-5-5, Bb-7-1, Bb-45-1, Bb-49-1, Bb-60-1, Bb-60-2, Bb -71-3, Bb-73-1, Bb-76-1, Bb-77-3, Bb-102-1, Bb-124-1, Bb-127-1, Bb-128-1, BB-130 -1, Bb-131-1, Bb-132-1, Bb-1-5, Bb-137-1, Bb-138-1, Bb-139-1, Bb-143-3, Bb-147-1 , Bb-152-1, Bb-156-1, Bb-157-1, Bb-159-1, Bb-162-1, Bb-49-2, Bb-137-2, Bb-138-2, Bb-139-2, Bb-262-1, Bb-265-1, Bc-1(R), Bc-1(S), Bc-48, Bc-49, Bc-72, Bc-73, Bc-60,

[0769] (1-12) Herbicidal effect on Solanum nigrum (stem and leaf treatment)

[0770] In order to confirm the herbicidal effect on black nightshade (Solanum nigrum), the following compounds were used and the same test method as in Test Example 1 (1-1) (stem and leaf treatment) was implemented. As a result, each composition containing the following compounds (each active ingredient amount was 125, 250, 500 or 1000 g / ha) showed a growth inhibition rate of 70% or more on black nightshade.

[0771] Compound (active ingredient amount: 1000g / ha): Comp No.Ba-3-1, Ba-19-1, Bb-3-1, Bb-8-1, Bb-19-1, Bb-20-1

[0772] Compounds (active ingredient amount: 500g / ha): Comp No. Aa-52-1, Aa-55-1, Aa-62-1, Aa-63-1, Aa-81-1, Ba-11-1, Ba-44-1, Ba-45-1, Ba-53-1, Ba-58-1, Ba-116-3, Ba-117-3, Ba-118-3, Bb-10-1, Bb-11-1, Bb-12-1, Bb-13-1, Bb-15-1, Bb-26-1, Bb-27-1, Bb-44 -1, Bb-50-1, Bb-55-1, Bb-61-1, Bb-80-1, Bb-80-2, Bb-126-2, Bb-1-4, Bb-142-1, Bb-144-1, Bb-145-1, Bb-146-1, Bb-148-1, Bb-149-1, Bb-150-1, Bb-151-1, Bb-153-1, Bb-154-1, Bb-158-1, Bb-50-2, Bc-126

[0773] Compounds (active ingredient amount: 250 g / ha): Comp No. Aa-1, Bb-1-1, Bb-46-3, Bb-48-1, Bb-79-3, Bb-114-3, Bb-123-3, Bb-135-3, Bb-163-3, Bb-164-3, Bb-165-3

[0774] Compounds (active ingredient amount: 125 g / ha): Comp No. Aa-5-1, Aa-7-1, Aa-8-1, Aa-10-1, Aa-10-2, Aa-11-1, Aa-13-1, Aa-14-1, Aa-26-1, Aa-27-1, Aa-28-1, Aa-29-1, Aa-30-1, Aa-31-1, Aa-32-1, Aa-33-1, Aa-34-1, Aa-1-2, Aa-44-1, Aa-45-1, Aa-48-1, Aa-49-1, Aa-50-1, Aa-51-1, Aa-53-1, Aa-58-3, Aa-60-1, Aa-61-1, Aa-64-1, Aa-66-1, Aa-67-1, Aa-76-1, Aa-78, Aa-82-1, Aa-86-1, Aa-88-1, Aa-94-1, Aa-95-1, Aa-96-1, Aa-131-1, Aa-170-1, Aa-176-1, Aa-177-1, Aa-178-1, Aa-180-1, Aa-182-1, Aa-183-1, Aa-211-1, Aa-216-1 (HCl salt), Aa-219-3, Aa-227-1, Aa-230-3, Aa-232-3, Aa-233-1, Aa-234-1, Aa-236-1, Aa-239-1, Aa-240-1, Aa-244-1, Aa-247-1, Aa-248-1, Aa-249-1, Aa-250-3, Aa-254-1, Aa-259-1, Aa-263-1, Aa-263-2, Aa-264-1, Aa-265-1, Aa-269-1, Aa-273-2, Ba-1-2, Ba-63-1, Ba-64-1, Ba-65-1, Ba-76-1, Ba-119-1, Ba-120-1, Ba-121-1, Ba-122-1, Ba-124-1, Ba-125-1, Bb-1-2, Bb-2-1, Bb-5-1, Bb-5-5, Bb-7-1, Bb-45-1, Bb-49-1, Bb-63-1, Bb-64-1, Bb-65-1, Bb-71-3, Bb-73-1, Bb-76-1, Bb-77-3, Bb-102-1, Bb-119-1, Bb-124-1, Bb-127-1, Bb-128-1, BB-130-1, Bb-131-1, Bb-132-1, Bb-1-5, Bb-137-1, Bb-141-1, Bb-143-3, Bb-147-1, Bb-152-1, Bb-155-1, Bb-156-1, Bb-157-1, Bb-159-1, Bb-160-1,Bb-161-1, Bb-162-1, Bb-49-2, Bb-262-1, Bb-265-1, Bb-267-1, Bc-1, Bc-5(R), Bc-5, Bc- 44. Bc-48, Bc-49, Bc-53, Bc-72, Bc-73, Bc-60, Bc-127, Bc-128, Bc-129, Bc-265, Bc-267,

[0775] Test Example 2: (2-1) Weed control effect on barnyard grass (soil treatment)

[0776] In a 1 / 300,000 hectare (ha) pot, dryland soil was placed, barnyardgrass (Echinochloa crus-galli) seeds were sown, and the soil was covered with about 1.5 cm. The compound of the present invention was weighed so as to reach a predetermined amount of effective ingredient, dissolved in acetone (containing 0.5 volume % of a surfactant (Triton X-100: manufactured by Kishida Chemical Co., Ltd.)) or dimethyl sulfoxide, and diluted with water equivalent to 1000 liters per hectare (containing 0.1 volume % of an agricultural spreading agent (Supafactant WK: manufactured by Maruwa Biochemical Co., Ltd.)) to obtain a spreading solution. The next day after sowing, the spreading solution was applied to the soil using a small sprayer.

[0777] After the treatment with the chemical, the growth state of each plant was visually observed on the 14th day. As a result, each composition containing the following compounds (each active ingredient amount was 125, 250, 500 or 1000 g / ha) showed a growth inhibition rate of 70% or more on barnyardgrass.

[0778] Compound (active ingredient amount: 1000g / ha): Comp No.Ba-3-1, Ba-19-1, Bb-3-1, Bb-8-1, Bb-19-1, Bb-20-1

[0779] Compounds (active ingredient amount: 500 g / ha): Comp No. Aa-52-1, Aa-55-1, Aa-62-1, Aa-63-1, Aa-81-1, Ba-11-1, Ba-44-1, Ba-45-1, Ba-53-1, Ba-58-1, Bb-2-1, Bb-9-1, Bb-10-1, Bb-11-1, Bb-15-1, Bb-44-1, Bb-50-1, Bb-55-1, Bb-60-1, Bb-61-1, Bb-80-1, Bb-80-2, Bb-102-1, Bb-126-2, Bb-128-1, Bb-130-1, Bb-131-1, Bb-132-1, Bb-138-1, Bb-139-1, Bb-142-1, Bb-144-1, Bb-146-1, Bb-147-1, Bb-148-1, Bb-149-1, Bb-150-1, Bb-153-1, Bb-154-1, Bb-158-1, Bb-49-2, Bb-61-2, Bb-50-2, Bc-3, Bc-126

[0780] Compounds (active ingredient amount: 250 g / ha): Comp No. Aa-1-1, Aa-3-1, Ba-1-1, Bb-1-1, Bb-46-3, Bb-48-1, Bb-79-3, Bb-114-3, Bb-123-3, Bb-133-3, Bb-134-3, Bb-135-3, Bb-75-3, Bb-136-3, Bb-72-3, Bb-163-3, Bb-164-3, Bb-165-3

[0781] Compound (active ingredient amount: 125 g / ha): Comp No. Aa-2-1, Aa-4-1, Aa-7-1, Aa-8-1, Aa-10-1, Aa-10-2, Aa-11-1, Aa-16-1, Aa-21-1, Aa-28-1, Aa-29-1, Aa-1-2, Aa-2-2, Aa-4-2, Aa-29-2, Aa-32-2, Aa-44-1, Aa-45-1, Aa-48-1, Aa-49-2, Aa-50-1, Aa-51-1, Aa-53-1, Aa-54-1, Aa-56-1, Aa-57-1, Aa-60-1, Aa-61-1, Aa-67-1, Aa-68-1, Aa-70-1, Aa-71-1, Aa-72-1, Aa-73-1, Aa-74-1, Aa-75-1, Aa-76-1, Aa-77-1, Aa-92-1, Aa-96-1, Aa-131-1, Aa-48-1 (Na salt), Aa-133-1, Aa-134-1, Aa-135-1, Aa-137-1, Aa-138-1, Aa-166-1, Aa-167-1, Aa-168-1, Aa-169-1, Aa-170-1, Aa-172-1, Aa-173-1, Aa-174-1, Aa-175-1, Aa-177-1, Aa-178-1, Aa-181-1, Aa-182-1, Aa-184-1, Aa-185-1, Aa-217-1, Aa-223-2, Aa-230-3, Aa-233-1, Aa-240-1, Aa-250-3, Aa-253-1, Aa-260-1, Aa-278-2, Aa-279-2, Aa-280-2, Aa-281-2, Ba-1-2, Ba-64-1, Ba-76-1, Ba-121-1, Ba-122-1, Bb-64-1, Bb-65-1, Bb-71-3, Bb-76-1, Bb-119-1, Bb-124-1, Bb-127-1, Bb-1-5, Bb-137-1, Bb-141-1, Bb-143-3, Bb-152-1, Bb-156-1, Bb-157-1, Bb-159-1, Bb-162-1, Bb-137-2, Bb-138-2, Bc-1, Bc-44, Bc-53, Bc-73, Bc-127, Bc-129

[0782] (2-2) Herbicidal effect on Digitaria sanguinalis (soil treatment)

[0783] In order to confirm the herbicidal effect on crabgrass (Digitaria sanguinalis), the following compounds were used and the same test method as in Test Example 2 (2-1) (soil treatment) was carried out. As a result, each composition containing the following compound (each active ingredient amount was 125, 250, 500 or 1000 g / ha) showed a growth inhibition rate of 70% or more on crabgrass.

[0784] Compound (active ingredient amount: 1000g / ha): Comp No.Ba-3-1, Ba-19-1, Bb-3-1, Bb-8-1, Bb-19-1, Bb-20-1

[0785] Compounds (active ingredient amount: 500g / ha): Comp No. Aa-9-2, Aa-52-1, Aa-55-1, Aa-62-1, Aa-63-1, Ba-11-1, Ba-44-1, Ba-45-1, Ba-53-1, Ba-58-1, Ba-116-3, Bb-2-1, Bb-10-1, Bb-11-1, Bb-12-1, Bb-13-1, Bb-15-1, Bb-44-1, Bb-50-1, Bb-55-1, Bb-60-1, Bb-60-2, Bb-61-1, Bb-80-1, Bb-80-2, Bb- b-102-1, Bb-126-2, Bb-128-1, Bb-130-1, Bb-131-1, Bb-1-4, Bb-138-1, Bb-139-1, Bb-142-1, Bb-144-1, Bb-145-1, Bb-14 6-1, Bb-147-1, Bb-148-1, Bb-149-1, Bb-150-1, Bb-153-1, Bb-154-1, Bb-158-1, Bb-49-2, Bb-61-2, Bb-50-2, Bc-3, Bc-126

[0786] Compounds (active ingredient amount: 250 g / ha): Comp No. Aa-1-1, Aa-3-1, Ba-1-1, Bb-1-1, Bb-46-3, Bb-48-1, Bb-79-3, Bb-114-3, Bb-123-3, Bb-133-3, Bb-134-3, Bb-135-3, Bb-75-3, Bb-136-3, Bb-72-3, Bb-163-3, Bb-164-3, Bb-165-3

[0787] Compound (active ingredient amount: 125 g / ha): Comp No. Aa-2-1, Aa-4-1, Aa-6-1, Aa-7-1, Aa-8-1, Aa-10-1, Aa-10-2, Aa-11-1, Aa-14-1, Aa-15-1, Aa-16-1, Aa-19-1, Aa-25-1, Aa-32-1, Aa-36-1, Aa-1-2, Aa-2-2, Aa-4-2, Aa-32-2, Aa-44-1, Aa-45-1, Aa-47-1, Aa-48-1, Aa-49-1, Aa-49-2, Aa-50-1, Aa-51-1, Aa-53-1, Aa-54-1, Aa-56-1, Aa-57-1, Aa-60-1, Aa-61-1, Aa-66-1, Aa-67-1, Aa-68-1, Aa-69-1, Aa-70-1, Aa-71-1, Aa-72-1, Aa-73-1, Aa-74-1, Aa-75-1, Aa-76-1, Aa-77-1, Aa-83-1, Aa-84-1, Aa-86-1, Aa-96-1, Aa-131-1, Aa-133-1, Aa-134-1, Aa-135-1, Aa-137-1, Aa-138-1, Aa-166-1, Aa-167-1, Aa-168-1, Aa-169-1, Aa-170-1, Aa-171-1, Aa-172-1, Aa-173-1, Aa-174-1, Aa-175-1, Aa-176-1, Aa-177-1, Aa-178-1, Aa-181-1, Aa-182-1, Aa-184-1, Aa-217-1, Aa-223-2, Aa-226-2, Aa-230-3, Aa-240-1, Aa-250-3, Aa-253-1, Aa-260-1, Aa-261-2, Aa-262-1, Aa-262-2, Aa-278-2, Aa-279-2, Aa-280-2, Aa-281-2, Ba-1-2, Ba-64-1, Ba-76-1, Ba-120-1, Ba-121-1, Ba-122-1, Bb-1-2, Bb-7-1, Bb-45-1, Bb-49-1, Bb-53-1, Bb-63-1, Bb-64-1, Bb-65-1, Bb-71-3, Bb-73-1, Bb-76-1, Bb-77-3, Bb-119-1, Bb-124-1, Bb-127-1, Bb-1-5, Bb-137-1, Bb-141-1, Bb-143-3, Bb-152-1, Bb-156-1, Bb-157-1, Bb-159-1, Bb-160-1,Bb-161-1, Bb-162-1, Bb-137-2, Bb-138-2, Bb-139-2, Bc-1, Bc-48, Bc-73, Bc-127, Bc-129, Bc-262,

[0788] (2-3) Weed control effect on Setaria viridis (soil treatment)

[0789] In order to confirm the herbicidal effect on green foxtail (Setaria viridis), the following compounds were used and the same test method as in Test Example 2 (2-1) (soil treatment) was implemented. As a result, each composition containing the following compounds (each active ingredient amount was 125, 250, 500 or 1000 g / ha) showed a growth inhibition rate of 70% or more on green foxtail.

[0790] Compound (active ingredient amount: 1000g / ha): Comp No.Ba-3-1, Ba-19-1, Bb-3-1, Bb-8-1, Bb-19-1, Bb-20-1

[0791] Compounds (active ingredient amount: 500g / ha): Comp No. Aa-52-1, Aa-55-1, Aa-63-1, Aa-81-1, Ba-11-1, Ba-44-1, Ba-45-1, Ba-53-1, Ba-58-1, Bb-2-1, Bb-10-1, Bb-11-1, Bb-12-1, Bb-15-1, Bb-44-1, Bb-50-1, Bb-55-1, Bb-60-1, Bb-60-2, Bb-61-1, Bb-80-1, Bb-80-2, Bb-10 2-1, Bb-126-2, Bb-128-1, Bb-131-1, Bb-138-1, Bb-139-1, Bb-142-1, Bb-144-1, Bb-145-1, Bb-146-1, Bb-147 -1, Bb-148-1, Bb-149-1, Bb-150-1, Bb-153-1, Bb-154-1, Bb-158-1, Bb-49-2, Bb-61-2, Bb-50-2, Bc-3, Bc-126

[0792] Compounds (active ingredient amount: 250 g / ha): Comp No. Aa-1-1, Aa-3-1, Ba-1-1, Bb-1-1, Bb-46-3, Bb-48-1, Bb-79-3, Bb-114-3, Bb-123-3, Bb-133-3, Bb-134-3, Bb-135-3, Bb-75-3, Bb-136-3, Bb-72-3, Bb-163-3, Bb-164-3, Bb-165-3

[0793] Compound (active ingredient amount: 125g / ha): Comp No.Aa-2-1, Aa-4-1, Aa-7-1, Aa-8-1, Aa-9-1, Aa-10-1, Aa-10-2, Aa-11-1, Aa-16-1, Aa-19-1, Aa-28-1, Aa-1-2, Aa-2-2, Aa-4-2, Aa-29-2, Aa-32-2, Aa-44-1, Aa-45-1, Aa-47-1, Aa-48-1, Aa-49-1, Aa-49-2, Aa-50-1, Aa-51-1, Aa-53-1, Aa-54-1, Aa-56-1, Aa-57-1, Aa-60-1, Aa-67-1, Aa-68-1, Aa-69-1, Aa-71-1, Aa-72-1, Aa-73-1, Aa-74-1, Aa-75-1, Aa-77-1, Aa-87-1, Aa-90-1, Aa-92-1, Aa-131-1, Aa-48-1 (Na salt), Aa-133-1, Aa-134-1, Aa-135-1, Aa-166-1, Aa-167-1, Aa-168-1, Aa-169-1, Aa-170-1, Aa-172-1, Aa-173-1, Aa-174-1, Aa-175-1, Aa-176-1, Aa-177-1, Aa-178-1, Aa-181-1, Aa-182-1, Aa-184-1, Aa-203-1, Aa-217-1, Aa-224-3, Aa-225-3, Aa-226-2, Aa-230-3, Aa-233-1, Aa-237-3, Aa-240-1, Aa-253-1, Aa-257-2, Aa-258-1, Aa-260-1, Aa-262-1, Aa-262-2, Aa-278-2, Aa-279-2, Aa-280-2, Aa-281-2, Ba-1-2, Ba-121-1, Ba-122-1, Bb-1-2, Bb-45-1, Bb-53-1, Bb-64-1, Bb-65-1, Bb-71-3, Bb-76-1, Bb-77-3, Bb-119-1, Bb-124-1, Bb-127-1, Bb-1-5, Bb-137-1, Bb-141-1, Bb-143-3, Bb-152-1, Bb-156-1, Bb-157-1, Bb-159-1, Bb-160-1, Bb-161-1, Bb-162-1, Bb-137-2, Bb-138-2, Bb-139-2, Bb-262-1, Bb-265-1, Bc-1, Bc-1(S), Bc-73, Bc-127, Bc-128, Bc-129, Bc-265.

[0794] (2-4) Weed control effect on multiflora ryegrass (soil treatment)

[0795] In order to confirm the herbicidal effect on Lolium multiflorum, the following compounds were used and the same test method as in Test Example 2 (2-1) (soil treatment) was carried out. As a result, each composition containing the following compound (each active ingredient amount was 125 or 500 g / ha) showed a growth inhibition rate of 70% or more on Lolium multiflorum.

[0796] Compounds (active ingredient amount: 500g / ha): Comp No. Aa-9-2, Aa-52-1, Aa-55-1, Aa-62-1, Aa-63-1, Ba-44-1, Ba-45-1, Ba-53-1, Bb-2-1, Bb-60-1, Bb-80-1, Bb-80-2, Bb-102-1, Bb-158-1

[0797] Compound (active ingredient amount: 125 g / ha): Comp No. Aa-2-1, Aa-4-1, Aa-6-1, Aa-7-1, Aa-8-1, Aa-9-1, Aa-10-1, Aa-10-2, Aa-11-1, Aa-12-1, Aa-13-1, Aa-14-1, Aa-15-1, Aa-16-1, Aa-17-1, Aa-19-1, Aa-20-1, Aa-21-1, Aa-25-1, Aa-27-1, Aa-28-1, Aa-29-1, Aa-33-1, Aa-34-1, Aa-36-1, Aa-1-2, Aa-12-2, Aa-2-2, Aa-4-2, Aa-29-2, Aa-44-1, Aa-45-1, Aa-47-1, Aa-48-1, Aa-49-1, Aa-49-2, Aa-50-1, Aa-51-1, Aa-53-1, Aa-54-1, Aa-56-1, Aa-57-1, Aa-58-3, Aa-60-1, Aa-61-1, Aa-64-1, Aa-66-1, Aa-67-1, Aa-68-1, Aa-71-1, Aa-72-1, Aa-73-1, Aa-74-1, Aa-75-1, Aa-76-1, Aa-77-1, Aa-85-2, Aa-86-1, Aa-87-1, Aa-89-1, Aa-90-1, Aa-92-1, Aa-101-1, Aa-102-3, Aa-103-2, Aa-113-1, Aa-115-1, Aa-131-1, Aa-48-1 (Na salt), Aa-133-1, Aa-134-1, Aa-135-1, Aa-137-1, Aa-138-1, Aa-156-3, Aa-166-1, Aa-167-1, Aa-168-1, Aa-169-1, Aa-170-1, Aa-171-1, Aa-172-1, Aa-173-1, Aa-174-1, Aa-175-1, Aa-176-1, Aa-177-1, Aa-178-1, Aa-180-1, Aa-181-1, Aa-182-1, Aa-184-1, Aa-185-1, Aa-203-1, Aa-210-1, Aa-217-1, Aa-218-1, Aa-223-3, Aa-224-3, Aa-225-3, Aa-223-2, Aa-226-1, Aa-226-2, Aa-230-3, Aa-233-1, Aa-235-1, Aa-237-3, Aa-240-1, Aa-244-1, Aa-250-3, Aa-253-1, Aa-255-1, Aa-257-1, Aa-257-2, Aa-258-1,Aa-260-1, Aa-261-2, Aa-262-1, Aa-262-2, Aa-263-1, Aa-277-2, Aa-278-2, Aa-279-2, Aa-2 80-2, Aa-281-2, Ba-1-2, Ba-76-1, Ba-119-1, Ba-121-1, Ba-122-1, Ba-124-1, Bb-1-2, Bb-6 4-1, Bb-71-3, Bb-76-1, Bb-77-3, Bb-124-1, Bb-127-1, Bb-156-1, Bb-159-1, Bb-160-1, Bb- 161-1, Bb-262-1, Bb-265-1, Bc-1, Bc-1(S), Bc-44, Bc-53, Bc-73, Bc-127, Bc-129, Bc-262,

[0798] (2-5) Weed control effect on Amaranthus retroflexus (soil treatment)

[0799] In order to confirm the herbicidal effect on redroot pigweed (Amaranthus retroflexus), the following compounds were used and the same test method as in Test Example 2 (2-1) (soil treatment) was implemented. As a result, each composition containing the following compound (each active ingredient amount was 125, 250, 500 or 1000 g / ha) showed a growth inhibition rate of 70% or more on redroot pigweed.

[0800] Compound (active ingredient amount: 1000g / ha): Comp No.Ba-3-1, Ba-19-1, Bb-3-1, Bb-8-1, Bb-19-1, Bb-20-1

[0801] Compounds (active ingredient amount: 500 g / ha): Comp No. Aa-9-2, Aa-52-1, Aa-62-1, Aa-63-1, Ba-11-1, Ba-44-1, Ba-45-1, Ba-53-1, Ba-58-1, Ba-118-3, Bb-2-1, Bb-9-1, Bb-10-1, Bb-11-1, Bb-12-1, Bb-15-1, Bb-44-1, Bb-50-1, Bb-55-1, Bb-60-1, Bb-61-1, Bb-80-1, Bb-80-2, Bb-102-1, Bb-126-2, Bb-128-1, Bb-130-1, Bb-131-1, Bb-132-1, Bb-138-1, Bb-139-1, Bb-142-1, Bb-144-1, Bb-146-1, Bb-147-1, Bb-149-1, Bb-150-1, Bb-153-1, Bb-154-1, Bb-158-1, Bb-49-2, Bb-61-2, Bb-50-2, Bc-3, Bc-126

[0802] Compounds (active ingredient amount: 250 g / ha): Comp No. Aa-1-1, Aa-3-1, Ba-1-1, Bb-1-1, Bb-46-3, Bb-48-1, Bb-79-3, Bb-114-3, Bb-123-3, Bb-133-3, Bb-134-3, Bb-135-3, Bb-75-3, Bb-136-3, Bb-72-3, Bb-163-3, Bb-164-3, Bb-165-3

[0803] Compound (active ingredient amount: 125 g / ha): Comp No.Aa-2-1, Aa-4-1, Aa-7-1, Aa-8-1, Aa-10-1, Aa-10-2, Aa-11-1, Aa-16-1, Aa-19-1, Aa-27-1, Aa-29-1, Aa-30-1, Aa-31-1, Aa-32-1, Aa-33-1, Aa-1-2, Aa-12-2, Aa-2-2, Aa-4-2, Aa-32-2, Aa-44-1, Aa-45-1, Aa-48-1, Aa-49-2, Aa-51-1, Aa-53-1, Aa-54-1, Aa-56-1, Aa-57-1, Aa-60-1, Aa-67-1, Aa-68-1, Aa-71-1, Aa-72-1, Aa-73-1, Aa-74-1, Aa-75-1, Aa-77-1, Aa-83-1, Aa-84-1, Aa-92-1, Aa-133-1, Aa-134-1, Aa-135-1, Aa-166-1, Aa-167-1, Aa-168-1, Aa-169-1, Aa-170-1, Aa-172-1, Aa-173-1, Aa-174-1, Aa-175-1, Aa-217-1, Aa-224-3, Aa-230-3, Aa-240-1, Aa-253-1, Aa-254-1, Aa-260-1, Aa-262-2, Aa-278-2, Aa-280-2, Aa-281-2, Ba-1-2, Ba-120-1, Ba-121-1, Ba-122-1, Bb-1-2, Bb-7-1, Bb-45-1, Bb-49-1, Bb-53-1, Bb-64-1, Bb-73-1, Bb-76-1, Bb-77-3, Bb-119-1, Bb-124-1, Bb-127-1, Bb-1-5, Bb-137-1, Bb-141-1, Bb-143-3, Bb-152-1, Bb-156-1, Bb-157-1, Bb-159-1, Bb-160-1, Bb-161-1, Bb-162-1, Bb-137-2, Bb-138-2, Bb-139-2, Bb-262-1, Bc-1, Bc-48, Bc-49, Bc-53, Bc-60, Bc-72, Bc-73, Bc-127, Bc-129, Bc-262

[0804] (2-6) Herbicidal effect on Kochia scoparia (soil treatment)

[0805] In order to confirm the herbicidal effect on mexican burningbush (Kochia scoparia), the following compounds were used and the same test method as in Test Example 2 (2-1) (soil treatment) was carried out. As a result, each composition containing the following compound (each active ingredient amount was 125, 250, 500 or 1000 g / ha) showed a growth inhibition rate of 70% or more on Kochia scoparia.

[0806] Compound (active ingredient amount: 1000g / ha): Comp No. Ba-19-1, Bb-3-1, Bb-8-1, Bb-20-1

[0807] Compounds (active ingredient amount: 500 g / ha): Comp No. Ba-11-1, Ba-58-1, Ba-117-3, Ba-118-3, Bb-9-1, Bb-10-1, Bb-11-1, Bb-12-1, Bb-13-1, Bb-15-1, Bb-27-1, Bb-44-1, Bb-50-1, Bb-55-1, Bb-61-1, Bb-126-2, Bb-128-1, Bb- b-131-1, Bb-132-1, Bb-138-1, Bb-139-1, Bb-142-1, Bb-144-1, Bb-146-1, Bb-147-1, Bb-148-1, Bb-149-1, Bb-150-1, Bb-153-1, Bb-154-1, Bb-49-2, Bb-50-2, Bc-3, Bc-126

[0808] Compounds (active ingredient amount: 250 g / ha): Comp No. Aa-1-1, Aa-3-1, Ba-1-1, Bb-1-1, Bb-46-3, Bb-48-1, Bb-79-3, Bb-114-3, Bb-123-3, Bb-133-3, Bb-134-3, Bb-135-3, Bb-75-3, Bb-136-3, Bb-72-3, Bb-163-3, Bb-164-3, Bb-165-3

[0809] Compounds (active ingredient amount: 125g / ha): Comp No. Aa-50-1, Bb-7-1, Bb-45-1, Bb-49-1, Bb-119-1, Bb-1-5, Bb-137-1, Bb-141-1, Bb-143-3, Bb-152-1, Bb-137-2, Bb-139-2

[0810] (2-7) Weed control effect on velvetleaf (soil treatment)

[0811] In order to confirm the herbicidal effect on velvetleaf (Abutilon theophrasti), the following compounds were used and the same test method as in Test Example 2 (2-1) (soil treatment) was carried out. As a result, each composition containing the following compound (each active ingredient amount was 125, 500 or 1000 g / ha) showed a growth inhibition rate of 70% or more on velvetleaf.

[0812] Compound (active ingredient amount: 1000g / ha): Comp No. Bb-3-1, Bb-8-1, Bb-19-1

[0813] Compounds (active ingredient amount: 500g / ha): Comp No. Ba-45-1, Bb-2-1, Bb-10-1, Bb-12-1, Bb-50-1, Bb-131-1, Bb-132-1, Bb-138-1, Bb-146-1, Bb-153-1, Bb-154-1, Bb-158-1

[0814] Compounds (active ingredient amount: 125g / ha): Comp No. Aa-45-1, Aa-224-3, Bb-76-1, Bb-119-1, Bb-157-1, Bc-129

[0815] Test Example 3: (3-1) Safety to rice (stem and leaf treatment)

[0816] In order to confirm the safety to rice (Oryza sativa), the following compounds were used and the same test method as in Test Example 1 (stem and leaf treatment) was carried out. As a result, each composition containing the following compounds (each active ingredient amount was 125 or 500 g / ha) showed a growth inhibition rate of less than 30% on rice, and safety was confirmed.

[0817] Compounds (active ingredient amount: 500g / ha): Comp No. Aa-43-1, Aa-52-1, Aa-55-1, Aa-62-1, Aa-63-1, Aa-81-1, Ba-45-1, Ba-58-1, Ba-116-3, Ba-117-3, Ba-118-3, Bb-26-1, Bb-55-1, Bb-61-1, Bb-80-1, Bb-144-1, Bb-145-1, Bb-146-1, Bb-148-1, Bb-150-1, Bb-151-1, Bb-153-1, Bb-154-1, Bb-61-2

[0818] Compound (active ingredient amount: 125 g / ha): Comp No. Aa-12-1, Aa-13-1, Aa-17-1, Aa-23-1, Aa-24-1, Aa-26-1, Aa-26-2, Aa-35-1, Aa-37, Aa-39-1, Aa-40-1, Aa-41-1, Aa-12-2, Aa-4-2, Aa-29-2, Aa-32-2, Aa-42-1, Aa-45-1, Aa-47-1, Aa-58-3, Aa-59, Aa-65-1, Aa-68-1, Aa-69-1, Aa-70-1, Aa-78, Aa-84-1, Aa-87-1, Aa-88-1, Aa-95-1, Aa-96-1, Aa-98-1, Aa-100-1, Aa-101-1, Aa-102-3, Aa-103-2, Aa-106-1, Aa-113-1, Aa-115-1, Aa-171-1, Aa-179-1, Aa-183-1, Aa-186-1, Aa-187-1, Aa-188-1, Aa-189-1, Aa-190-1, Aa-191-1, Aa-192-1, Aa-193-1, Aa-194-1, Aa-195-1, Aa-196-1, Aa-197-1, Aa-198-1, Aa-199-1, Aa-200-1, Aa-201-1, Aa-202-1, Aa-203-1, Aa-204-1, Aa-205-1, Aa-206-1, Aa-207-1, Aa-208-1, Aa-209-1, Aa-210-1, Aa-211-1, Aa-213-1, Aa-214-1, Aa-216-1 (HCl salt), Aa-222-3, Aa-234-1, Aa-237-3, Aa-239-1, Aa-245-1, Aa-245-2, Aa-246-1, Aa-251-1, Aa-252-1, Aa-255-1, Aa-256-1, Aa-257-2, Aa-259-1, Aa-259-2, Aa-262-2, Aa-264-1, Aa-265-1, Aa-265-2, Aa-266-1, Aa-266-2, Aa-267-1, Aa-267-2, Aa-268-1, Aa-269-1, Aa-270-2, Aa-271-1, Aa-271-2, Aa-272-1, Aa-272-2, Aa-273-2, Aa-274-1, Aa-274-2, Aa-275-2, Aa-275-1, Aa-276-1, Aa-276-2, Aa-277-1, Aa-282-2, Aa-283-2, Aa-284-2,Aa-286-2, Aa-287-1, Ba-9-1, Ba-63-1, Ba-64-1, Ba-65-1, Ba-76-1, Ba-119-1, Ba-124- 1. Ba-125-1, Ba-226-1, Bb-45-1, Bb-60-1, Bb-63-1, Bb-64-1, Bb-65-1, Bb-76-1, Bb-119 -1, Bb-124-1, Bb-128-1, BB-130-1, Bb-141-1, Bb-152-1, Bb-155-1, Bb-157-1, Bb-162-1 , Bb-265-1, Bb-267-1, Bc-1(R), Bc-3, Bc-5, Bc-129, Bc-223-1, Bc-262, Bc-265, Bc-267,

[0819] (3-2) Safety to corn (stem and leaf treatment)

[0820] In order to confirm the safety for corn (Zea mays), the following compounds were used and the same test method as in Test Example 1 (stem and leaf treatment) was implemented. As a result, each composition containing the following compounds (each active ingredient amount was 125 or 500 g / ha) showed a growth inhibition rate of less than 30% for each corn, and safety was confirmed.

[0821] Compounds (active ingredient amount: 500g / ha): Comp No. Aa-42-1, Aa-43-1, Aa-52-1, Ba-116-3, Ba-118-3, Bb-61-1, Bb-148-1

[0822] Compounds (active ingredient amount: 125 g / ha): Comp No. Aa-24-1, Aa-37, Aa-40-1, Aa-47-1, Aa-58-3, Aa-59, Ba-9-1, Ba-63-1, Ba-65-1, Ba-76-1, Ba-124-1, Ba-125-1, Bb-63-1, Bb-65-1, Bb-119-1, Bb-124-1, Bb-1 55-1, Bb-162-1, Aa-183-1, Aa-187-1, Aa-188-1, Aa-216-1 (HCl salt), Aa-231, Aa-2 39-1, Aa-251-1, Aa-266-2, Aa-275-2, Aa-275-1, Aa-276-2, Aa-287-1, Aa-287-2

[0823] (3-3) Safety to wheat (stem and leaf treatment)

[0824] In order to confirm the safety for wheat (Triticum aestivum), the following compounds were used and the same test method as in Test Example 1 (stem and leaf treatment) was implemented. As a result, each composition containing the following compounds (each active ingredient amount was 125, 250 or 500 g / ha) showed a growth inhibition rate of less than 30% on wheat, and safety was confirmed.

[0825] Compounds (active ingredient amount: 500g / ha): Comp No. Aa-43-1, Aa-52-1, Aa-55-1, Ba-58-1, Ba-116-3, Ba-117-3, Ba-118-3, Bb-144-1, Bb-146-1, Bb-148-1, Bb-150-1, Bb-151-1, Bb-154-1, Bb-158-1

[0826] Compound (active ingredient amount: 125g / ha): Comp No.Aa-24-1, Aa-35-1, Aa-37, Aa-40-1, Aa-45-1, Aa-51-1, Aa-58-3, Aa-95-1, Aa-96-1, Aa-98-1, Aa-100-1, Ba-9-1, Ba-63-1, Ba-65-1, B a-76-1, Ba-121-1, Ba-122-1, Ba-124-1, Bb-45-1, Bb-63-1, Bb-65-1, Bb-124-1, Bb-128-1, Bb-152-1, Bb-155-1, Bb-157-1, Bb-162-1, Bc- 129. Aa-187-1, Aa-188-1, Aa-189-1, Aa-200-1, Aa-210-1, Aa-211-1, Aa-216-1 (HCl salt), Aa-239-1, Aa-245-1, Aa-245-2, Aa-251-1, Aa-266 -1, Aa-266-2, Aa-268-1, Aa-270-2, Aa-272-1, Aa-274-2, Aa-275-2, Aa-276-2, Aa-285-2, Aa-286-2, Aa-287-1, Aa-287-2, Bc-262, Bc-267

[0827] (3-4) Safety of soybeans (stem and leaf treatment)

[0828] In order to confirm the safety for soybean (Glycine max), the following compounds were used and the same test method as in Test Example 1 (stem and leaf treatment) was implemented. As a result, each composition containing the following compounds (each active ingredient amount was 125 or 500 g / ha) showed a growth inhibition rate of less than 30% for soybean, and safety was confirmed.

[0829] Compounds (active ingredient amount: 500g / ha): Comp No. Aa-42-1, Aa-43-1, Aa-52-1, Aa-55-1, Ba-53-1, Ba-117-3, Ba-118-3, Bb-12-1, Bb-26-1, Bb-27-1, Bb-44-1, Bb-55-1, Bb-80-1, Bb-80-2, Bb-149-1, Bb-150-1, Bb-61-2, Bb-50-2

[0830] Compound (active ingredient amount: 125 g / ha): Comp No. Aa-9-2, Aa-10-2, Aa-13-1, Aa-17-1, Aa-18-1, Aa-22-1, Aa-23-1, Aa-24-1, Aa-26-1, Aa-26-2, Aa-30-1, Aa-31-1, Aa-33-1, Aa-35-1, Aa-37, Aa-39-1, Aa-40-1, Aa-41-1, Aa-12-2, Aa-2-2, Aa-4-2, Aa-29-2, Aa-32-2, Aa-23-2, Aa-45-1, Aa-47-1, Aa-51-1, Aa-59, Aa-68-1, Aa-69-1, Aa-84-1, Aa-85-1, Aa-85-2, Aa-87-1, Aa-88-1, Aa-89-1, Aa-95-1, Aa-96-1, Aa-98-1, Aa-100-1, Aa-101-1, Aa-103-1, Aa-103-2, Aa-171-1, Aa-177-1, Aa-179-1, Aa-183-1, Aa-185-1, Aa-186-1, Aa-187-1, Aa-188-1, Aa-189-1, Aa-190-1, Aa-191-1, Aa-192-1, Aa-193-1, Aa-197-1, Aa-198-1, Aa-200-1, Aa-202-1, Aa-203-1, Aa-207-1, Aa-209-1, Aa-211-1, Aa-213-1, Aa-214-1, Aa-216-1 (HCl salt), Aa-218-1, Aa-219-3, Aa-220-3, Aa-224-3, Aa-223-2, Aa-220-2, Aa-226-2, Aa-229-2, Aa-231, Aa-237-3, Aa-239-1, Aa-241-1, Aa-242-1, Aa-245-1, Aa-245-2, Aa-246-1, Aa-251-1, Aa-252-1, Aa-253-1, Aa-255-1, Aa-256-1, Aa-257-2, Aa-258-1, Aa-259-2, Aa-261-2, Aa-265-1, Aa-265-2, Aa-266-1, Aa-266-2, Aa-267-2, Aa-269-1, Aa-270-2, Aa-271-1, Aa-271-2, Aa-272-1, Aa-272-2, Aa-273-2, Aa-274-1, Aa-274-2, Aa-275-2, Aa-275-1, Aa-276-1, Aa-276-2, Aa-277-1, Aa-277-2,Aa-278-2, Aa-281-2, Aa-282-2, Aa-283-2, Aa-284-2, Aa-285-2, Aa-286-2, Aa-287 -1, Aa-287-2, Ba-9-1, Ba-63-1, Ba-119-1, Ba-120-1, Ba-121-1, Ba-124-1, Ba-125 -1, Ba-223-1, Bb-53-1, Bb-132-1, Bb-147-1, Bb-155-1, Bb-138-2, Bb-139-2, Bc-1 , Bc-1(R), Bc-1(S), Bc-3, Bc-44, Bc-49, Bc-53, Bc-128, Bc-223-1, Bc-262, Bc-267,

[0831] (3-5) Safety to rapeseed (stem and leaf treatment)

[0832] In order to confirm the safety to rapeseed (Brassica napus), the following compounds were used and the same test method as in Test Example 1 (stem and leaf treatment) was implemented. As a result, each composition containing the following compounds (each active ingredient amount was 125 or 500 g / ha) showed a growth inhibition rate of less than 30% on rapeseed, and safety was confirmed.

[0833] Compounds (active ingredient amount: 500g / ha): Comp Aa-42-1, Aa-43-1, Aa-52-1, Aa-55-1, Ba-44-1, Ba-53-1, Bb-12-1, Bb-27-1

[0834] Compound (active ingredient amount: 125 g / ha): Comp No. Aa-9-2, Aa-16-1, Aa-18-1, Aa-22-1, Aa-25-1, Aa-35-1, Aa-37, Aa-39-1, Aa-40-1, Aa-41-1, Aa-12-2, Aa-2-2, Aa-4-2, Aa-29-2, Aa-32-2, Aa-22-2, Aa-23-2, Aa-50-1, Aa-51-1, Aa-53-1, Aa-69-1, Aa-70-1, Aa-84-1, Aa-85-1, Aa-85-2, Aa-87-1, Aa-101-1, Aa-103-1, Aa-103-2, Aa-104-1, Aa-106-1, Aa-108-1, Aa-109-1, Aa-110-1, Aa-111-1, Aa-112-1, Aa-156-3, Aa-186-1, Aa-187-1, Aa-189-1, Aa-190-1, Aa-191-1, Aa-192-1, Aa-195-1, Aa-200-1, Aa-201-1, Aa-202-1, Aa-203-1, Aa-205-1, Aa-206-1, Aa-209-1, Aa-211-1, Aa-212-1, Aa-213-1, Aa-214-1, Aa-215-1, Aa-216-1 (HCl salt), Aa-218-1, Aa-220-3, Aa-221-3, Aa-222-3, Aa-220-2, Aa-228-2, Aa-229-2, Aa-231, Aa-237-3, Aa-238-1, Aa-239-1, Aa-242-1, Aa-243-1, Aa-245-1, Aa-245-2, Aa-251-1, Aa-252-1, Aa-253-1, Aa-255-1, Aa-256-1, Aa-257-2, Aa-259-1, Aa-259-2, Aa-261-2, Aa-262-2, Aa-263-1, Aa-265-2, Aa-266-1, Aa-266-2, Aa-267-1, Aa-267-2, Aa-268-1, Aa-269-1, Aa-270-2, Aa-271-1, Aa-271-2, Aa-272-1, Aa-272-2, Aa-273-2, Aa-274-1, Aa-274-2, Aa-275-2, Aa-275-1, Aa-276-1, Aa-276-2, Aa-277-1, Aa-277-2, Aa-282-2, Aa-283-2, Aa-284-2, Aa-285-2, Aa-286-2, Aa-287-1, Aa-287-2Ba-9-1, Ba-119-1, Ba-120-1, Ba-121-1, Bb-155-1, Bc-267,

[0835] Test Example 4: (4-1) Safety to rice (soil treatment)

[0836] In order to confirm the safety to rice (Oryza sativa), the following compounds were used and the same test method as in Test Example 2 (soil treatment) was carried out. As a result, each composition containing the following compounds (each active ingredient amount was 125, 250 or 500 g / ha) showed a growth inhibition rate of less than 30% on rice, and safety was confirmed.

[0837] Compounds (active ingredient amount: 500g / ha): Comp No. Aa-52-1, Aa-55-1, Aa-62-1, Aa-63-1, Aa-81-1, Ba-116-3, Ba-117-3, Ba-118-3, Bb-12-1, Bb-27-1, Bb-61-1, Bb-128-1, Bb-130-1, Bb-132-1, Bb-144-1, Bb-145-1, Bb-146-1, Bb-148-1, Bb-150-1, Bb-151-1, Bb-154-1

[0838] Compound (active ingredient amount: 250g / ha): Comp No.Ba-1, Bb-1-1

[0839] Compound (active ingredient amount: 125 g / ha): Comp No. Aa-6-1, Aa-9-1, Aa-11-1, Aa-12-1, Aa-13-1, Aa-14-1, Aa-16-1, Aa-17-1, Aa-19-1, Aa-20-1, Aa-21-1, Aa-25-1, Aa-27-1, Aa-28-1, Aa-29-1, Aa-30-1, Aa-31-1, Aa-32-1, Aa-33-1, Aa-34-1, Aa-36-1, Aa-12-2, Aa-29-2, Aa-32-2, Aa-45-1, Aa-47-1, Aa-58-3, Aa-64-1, Aa-68-1, Aa-69-1, Aa-70-1, Aa-76-1, Aa-83-1, Aa-84-1, Aa-85-2, Aa-86-1, Aa-87-1, Aa-89-1, Aa-90-1, Aa-96-1, Aa-101-1, Aa-102-3, Aa-103-2, Aa-113-1, Aa-115-1, Aa-156-3, Aa-171-1, Aa-180-1, Aa-182-1, Aa-185-1, Aa-203-1, Aa-210-1, Aa-218-1, Aa-223-3, Aa-224-3, Aa-225-3, Aa-226-1, Aa-226-2, Aa-235-1, Aa-237-3, Aa-244-1, Aa-250-3, Aa-254-1, Aa-255-1, Aa-257-1, Aa-257-2, Aa-258-1, Aa-261-2, Aa-262-1, Aa-262-2, Aa-263-1, Aa-277-2, Ba-64-1, Ba-76-1, Ba-119-1, Ba-124-1, Bb-7-1, Bb-45-1, Bb-63-1, Bb-64-1, Bb-65-1, Bb-73-1, Bb-76-1, Bb-119-1, Bb-124-1, Bb-141-1, Bb-152-1, Bb-156-1, Bb-157-1, Bb-162-1, Bb-262-1, Bb-265-1, Bc-44, Bc-48, Bc-49, Bc-53, Bc-60, Bc-72, Bc-128, Bc-262, Bc-265

[0840] (4-2) Safety for corn (soil treatment)

[0841] In order to confirm the safety for corn (Zea mays), the following compounds were used and the same test method as in Test Example 2 (soil treatment) was implemented. As a result, each composition containing the following compounds (each active ingredient amount was 125, 250 or 500 g / ha) showed a growth inhibition rate of less than 30% for corn, and safety was confirmed.

[0842] Compounds (active ingredient amount: 500g / ha): Comp No. Aa-81-1, Ba-11-1, Ba-117-3, Bb-10-1, Bb-11-1, Bb-12-1, Bb-13-1, Bb-27-1, Bb-60-1, Bb-60-2, Bb-61-1, Bb-80-1, Bb-128-1, Bb-130-1, Bb-1-4, Bb-142-1, Bb-144-1, Bb-145-1, Bb-148-1, Bb-150-1, Bb-151-1, Bb-61-2

[0843] Compound (active ingredient amount: 250g / ha): Comp No.Ba-1, Bb-114-3

[0844] Compound (active ingredient amount: 125g / ha): Comp No.Aa-12-1, Aa-13-1, Aa-14-1, Aa-17-1, Aa-20-1, Aa-28-1, Aa-29-1, Aa- 30-1, Aa-31-1, Aa-32-1, Aa-33-1, Aa-12-2, Aa-45-1, Aa-47-1, Aa-70-1, Aa -76-1, Aa-83-1, Aa-85-2, Aa-89-1, Aa-96-1, Aa-101-1, Aa-102-3, Aa-103 -2, Aa-156-3, Aa-180-1, Aa-185-1, Aa-203-1, Aa-210-1, Aa-218-1, Aa-235 -1, Aa-244-1, Aa-250-3, Aa-254-1, Aa-255-1, Aa-260-1, Aa-261-2, Aa-26 2-1, Aa-262-2, Aa-263-1, Ba-64-1, Ba-124-1, Bb-7-1, Bb-45-1, Bb-63-1, B b-65-1, Bb-119-1, Bb-1-5, Bb-137-1, Bb-141-1, Bb-152-1, Bb-157-1, Bb-1 62-1, Bb-137-2, Bb-139-2, Bb-262-1, Bc-53, Bc-60, Bc-72, Bc-262, Bc-265

[0845] (4-3) Safety to wheat (soil treatment)

[0846] In order to confirm the safety for wheat (Triticum aestivum), the following compounds were used and the same test method as in Test Example 2 (soil treatment) was implemented. As a result, each composition containing the following compounds (each active ingredient amount was 125 or 500 g / ha) showed a wheat growth inhibition rate of less than 30%, and safety was confirmed.

[0847] Compounds (active ingredient amount: 500g / ha): Comp No. Aa-52-1, Aa-81-1, Ba-45-1, Ba-116-3, Ba-117-3, Bb-12-1, Bb-13-1, Bb-27-1, Bb-61-1, Bb-128-1, Bb-130-1, Bb-144-1, Bb-145-1, Bb-146-1, Bb-148-1, Bb-150-1, Bb-151-1, Bb-154-1

[0848] Compound (active ingredient amount: 125g / ha): Comp No.Aa-12-1, Aa-13-1, Aa-14-1, Aa-28-1, Aa-29-1, Aa-30-1, Aa-31-1, Aa-32-1, Aa-33-1, Aa-45-1, Aa-69-1, Aa-70 -1, Aa-76-1, Aa-84-1, Aa-86-1, Aa-96-1, Aa-101-1, Aa-102-3, Aa-103-2, Aa-156-3, Aa-203-1, Aa-235-1, Aa-250-3 , Aa-254-1, Aa-261-2, Aa-262-1, Aa-262-2, Ba-64-1, Ba-76-1, Ba-119-1, Ba-124-1, Bb-7-1, Bb-45-1, Bb-63-1, Bb -64-1, Bb-65-1, Bb-76-1, Bb-119-1, Bb-124-1, Bb-152-1, Bb-157-1, Bb-162-1, Bc-1, Bc-1(S), Bc-44, Bc-53, Bc-60

[0849] (4-4) Safety of soybeans (soil treatment)

[0850] In order to confirm the safety for soybean (Glycine max), the following compounds were used and the same test method as in Test Example 2 (soil treatment) was implemented. As a result, each composition containing the following compounds (each active ingredient amount was 125, 250, 500 or 1000 g / ha) showed a growth inhibition rate of less than 30% for soybean, and safety was confirmed.

[0851] Compound (active ingredient amount: 1000g / ha): Comp No. Ba-3-1, Bb-19-1, Bb-20-1

[0852] Compounds (active ingredient amount: 500g / ha): Comp No. Aa-9-2, Aa-52-1, Aa-55-1, Aa-62-1, Aa-63-1, Aa-81-1, Ba-11-1, Ba-53-1, Ba-58-1, Ba-116-3, Ba-117-3, Ba-118-3, Bb-9-1, Bb-10-1, Bb-11-1, Bb-12-1, Bb-13-1, Bb-27-1, Bb-55-1, Bb-60-1, Bb-60-2, Bb-61- 1. Bb-80-1, Bb-102-1, Bb-128-1, Bb-130-1, Bb-132-1, Bb-1-4, Bb-142-1, Bb-144-1, Bb-145-1, Bb-146-1, Bb-148-1, Bb-149-1, Bb-150-1, Bb-151-1, Bb-153-1, Bb-154-1, Bb-158-1, Bb-61-2, Bb-50-2, Bc-3, Bc-126

[0853] Compounds (active ingredient amount: 250 g / ha): Comp No. Aa-3-1, Ba-1-1, Bb-133-3, Bb-134-3, Bb-135-3, Bb-136-3

[0854] Compound (active ingredient amount: 125 g / ha): Comp No. Aa-2-1, Aa-4-1, Aa-6-1, Aa-7-1, Aa-8-1, Aa-9-1, Aa-10-1, Aa-11-1, Aa-12-1, Aa-13-1, Aa-14-1, Aa-15-1, Aa-16-1, Aa-17-1, Aa-19-1, Aa-20-1, Aa-21-1, Aa-25-1, Aa-27-1, Aa-28-1, Aa-29-1, Aa-30-1, Aa-31-1, Aa-32-1, Aa-33-1, Aa-34-1, Aa-36-1, Aa-1-2, Aa-12-2, Aa-2-2, Aa-4-2, Aa-29-2, Aa-32-2, Aa-44-1, Aa-45-1, Aa-47-1, Aa-49-2, Aa-50-1, Aa-51-1, Aa-54-1, Aa-56-1, Aa-58-3, Aa-60-1, Aa-61-1, Aa-64-1, Aa-66-1, Aa-67-1, Aa-68-1, Aa-69-1, Aa-70-1, Aa-71-1, Aa-72-1, Aa-73-1, Aa-75-1, Aa-76-1, Aa-83-1, Aa-84-1, Aa-85-2, Aa-86-1, Aa-87-1, Aa-89-1, Aa-90-1, Aa-92-1, Aa-96-1, Aa-101-1, Aa-102-3, Aa-103-2, Aa-113-1, Aa-115-1, Aa-131-1, Aa-48-1 (Na salt), Aa-137-1, Aa-138-1, Aa-156-3, Aa-166-1, Aa-167-1, Aa-168-1, Aa-169-1, Aa-171-1, Aa-172-1, Aa-173-1, Aa-174-1, Aa-175-1, Aa-176-1, Aa-177-1, Aa-178-1, Aa-180-1, Aa-181-1, Aa-182-1, Aa-184-1, Aa-185-1, Aa-203-1, Aa-210-1, Aa-217-1, Aa-218-1, Aa-223-3, Aa-223-2, Aa-226-1, Aa-226-2, Aa-230-3, Aa-233-1, Aa-235-1, Aa-237-3, Aa-244-1, Aa-250-3, Aa-254-1, Aa-255-1, Aa-257-1, Aa-257-2, Aa-258-1, Aa-261-2, Aa-262-1, Aa-262-2, Aa-277-2, Aa-278-2,Aa-280-2, Aa-281-2, Ba-1-2, Ba-64-1, Ba-76-1, Ba-119-1, Ba-120-1, Ba-121-1, Ba-122-1, Ba-124-1, Bb-1-2, Bb-7-1, Bb-45-1, Bb-63-1, Bb-64-1, Bb-65-1, Bb-73-1, Bb-76-1, Bb-119-1, Bb-124-1, Bb-127 -1, Bb-1-5, Bb-141-1, Bb-156-1, Bb-157-1, Bb-159-1, Bb-160-1, Bb-161-1, Bb-162-1, Bb-138-2, Bb-1 39-2, Bb-262-1, Bb-265-1, Bc-1, Bc-1(S), Bc-44, Bc-48, Bc-53, Bc-60, Bc-72, Bc-127, Bc-128, Bc-265,

[0855] Next, the following comparative test was conducted to show the herbicidal effect of the composition containing compound 4b described in Patent Document 1 (China Patent Application Publication No. 109896973) and the present composition on undesirable plants. It should be noted that the structures of the test compounds in the comparative test are shown in Table 3 below.

[0856] Table 3

[0857]

[0858] Comparative test 1: Weed control effect on undesirable plants (stem and leaf treatment)

[0859] In a 1 / 300,000 hectare (ha) pot, dryland cultivated soil was placed, and seeds of barnyardgrass (Echinochloa crus-galli), crabgrass (Digitaria sanguinalis), green foxtail (Setaria viridis), wild oat (Avena fatua), italian ryegrass (Lolium multiflorum), foxtail shortawn (Alopecurus aequalis), annual bluegrass (Poa annua), redroot pigweed (Amaranthus retroflexus), common chickweed (Stellaria media), common lambsquarters (Chenoqodium album), and black nightshade (Solanum nigrum) were sown and covered with about 1.5 cm of soil. Then, the plants were cultivated in a greenhouse for 10 days until the specified leaf age was reached. The compounds of the present invention (Aa-1-1, Aa-9-2) or compound 4b described in Patent Document 1 were weighed in such a manner that the specified amount of effective ingredient was reached, dissolved using acetone (containing 0.5% by volume of a surfactant (BRIBO X-100: manufactured by Kishida Chemical Co., Ltd.)) or dimethyl sulfoxide, and diluted in water equivalent to 1000 liters per hectare (containing 0.1% by volume of an agricultural spreading agent (SUFACTAN WK: manufactured by Maruwa Biochemical Co., Ltd.)) to prepare each dispersion liquid. After cultivation, each prepared dispersion liquid was applied to the stems and leaves using a small sprayer. After treatment with the agent, the growth status of various plants was visually observed on the 14th day, and the herbicidal effect was evaluated by the growth inhibition rate (%) of 0 (equivalent to the untreated area) to 100 (completely dead). The results are shown in Table 4. A represents a growth inhibition rate of 90% or more, B represents a growth inhibition rate of 70% or more and less than 90%, C represents a growth inhibition rate of 50% or more and less than 70%, D represents a growth inhibition rate of 30% or more and less than 50%, and E represents a growth inhibition rate of less than 30%.

[0860] Table 4

[0861]

[0862] Comparative test 2: Weed control effect on undesirable plants (soil treatment)

[0863] In a 1 / 300,000 hectare (ha) pot, dryland crop soil was placed, and seeds of barnyardgrass (Echinochloa crus-galli), crabgrass (Digitaria sanguinalis), greenfoxtail (Setaria viridis), italian ryegrass (Lolium multiflorum), redroot pigweed (Amaranthus retroflexus), and common chickweed (Stellaria media) were sown and covered with about 1.5 cm of soil. The compound of the present invention (Aa-1-1, Aa-9-2) or compound 4b described in Patent Document 1 was weighed in such a manner as to achieve a predetermined amount of effective ingredient, dissolved in acetone (containing 0.5% by volume of a surfactant (BRIBO X-100: manufactured by Kishida Chemical Co., Ltd.)) or dimethyl sulfoxide, and diluted in water (containing 0.1% by volume of an agricultural spreading agent (SUFACTAN WK: manufactured by Maruwa Biochemical Co., Ltd.)) equivalent to 1000 liters per hectare to prepare each spreading solution. The soil was treated with each spreading solution using a small sprayer the day after sowing. After the treatment with the drug, the growth state of each plant was visually observed on the 14th day, and the herbicidal effect was evaluated by the growth inhibition rate (%) of 0 (equivalent to the untreated area) to 100 (completely dead). The results are shown in Table 5. A represents a growth inhibition rate of 90% or more, B represents a growth inhibition rate of 70% or more and less than 90%, C represents a growth inhibition rate of 50% or more and less than 70%, D represents a growth inhibition rate of 30% or more and less than 50%, and E represents a growth inhibition rate of less than 30%.

[0864] Table 5

[0865]

[0866] Next, the preparation examples of the present composition are described, but the compounding ratio, dosage form, etc. are not limited to the described examples.

[0867] Preparation Example 1

[0868] (1) 50 parts by weight of the compound of the present invention

[0869] (2) 2 parts by weight of alkylnaphthalene sulfonate formaldehyde condensate

[0870] (3) 0.2 parts by weight of silicone oil

[0871] (4) Water 47.8 parts by weight

[0872] Further add the above substances to the stock solution formed by uniformly mixing and grinding

[0873] (5) 5 parts by weight of sodium polycarboxylate

[0874] (6) 42.8 parts by weight of anhydrous sodium sulfate

[0875] The mixture is uniformly mixed, granulated and dried to prepare a granular hydrating agent.

[0876] Preparation Example 2

[0877] (1) 68 parts by weight of clay

[0878] (2) 2 parts by weight of sodium lignin sulfonate

[0879] (3) 5 parts by weight of polyoxyethylene styrylphenyl ether ammonium sulfate

[0880] (4) 25 parts by weight of white carbon black

[0881] The mixture of the above ingredients and the compound of the present invention are mixed in a weight ratio of 4:1 to prepare a hydrate.

[0882] Preparation Example 3

[0883] (1) 20 parts by weight of the compound of the present invention

[0884] (2) 70 parts by weight of clay

[0885] (3) 5 parts by weight of white carbon black

[0886] (4) 3 parts by weight of polycarboxylate

[0887] (5) 2 parts by weight of sodium alkylnaphthalene sulfonate

[0888] The above materials are uniformly mixed to prepare a hydrating agent.

[0889] Preparation Example 4

[0890] (1) 5 parts by weight of the compound of the present invention

[0891] (2) 1 part by weight of polyoxyethylene styryl phenyl ether

[0892] (3) 0.1 parts by weight of polyoxyethylene alkyl ether phosphate

[0893] (4) 93.9 parts by weight of granular calcium carbonate

[0894] (1) to (3) are uniformly mixed in advance, diluted with an appropriate amount of acetone, and then sprayed onto (4), and the acetone is removed to prepare granules.

[0895] Preparation Example 5

[0896] (1) 20 parts by weight of the compound of the present invention

[0897] (2) 20 parts by weight of N,N-dimethylacetamide

[0898] (3) 10 parts by weight of polyoxyethylene styryl phenyl ether

[0899] (4) 2 parts by weight of calcium dodecylbenzenesulfonate

[0900] (5) 48 parts by weight of xylene

[0901] The above substances are uniformly mixed and dissolved to form an emulsion.

[0902] Preparation Example 6

[0903] (1) 10 parts by weight of the compound of the present invention

[0904] (2) 80 parts by weight of diethylene glycol monoethyl ether

[0905] (3) 10 parts by weight of polyoxyethylene alkyl ether

[0906] Mix the above materials evenly to prepare a liquid.

[0907] Preparation Example 7

[0908] (1) 20 parts by weight of the compound of the present invention

[0909] (2) 2 parts by weight of polyoxyethylene styrylphenyl ether potassium phosphate

[0910] (3) 0.2 parts by weight of silicone oil

[0911] (4) 0.1 parts by weight of xanthan gum

[0912] (5) 5 parts by weight of ethylene glycol

[0913] (6) Water 72.7 parts by weight

[0914] The above materials are uniformly mixed and crushed to prepare a water suspension.

[0915] It should be noted that the entire contents of the specification, claims, and abstract of Japanese Patent Application No. 2022-094501 filed on June 10, 2022 are cited herein and incorporated as the contents of the specification of the present invention.

Claims

1. A herbicidal composition containing a difluorocrotonamide compound represented by formula (I) or a salt thereof as an active ingredient; In the formula, R 1 and R 2 Each is a halogen, may be replaced by at least one Y 1 Substituted (C1-C6)-chain hydrocarbon radical, (C1-C6)-alkoxy radical which may be substituted by at least one halogen, cyano radical or H; R 3 is H or fluorine atom, but excludes R 1 , R 2 and R 3 All are H cases; Y 1 is halogen, (C1-C6)-alkoxy or cyano; t is 1 or 2; R 4 -C(=O)OR 5 、-C(=O)SR 6 、-C(=O)NR 7 R 8 、-C(=O)R 9 , can be at least one Z 3 Substituted (C1-C6)-chain hydrocarbon group, -C(=O)H, -N(R 10 )C(=O)R 11 、-SR 6 、-S(=O)R 6 、-S(=O)2R 6 , =CHC(=O)R 11 , cyano, OH, 1,3-dioxolan-2-yl, 2-thiazolyl, may be replaced by at least one Z 4 Substituted 2-imidazolyl, =CHCH=CHC(=O)R 11 、-(C=O)2R 11 、-C(=NR 11 )-C(=O)R 11 or -CH(OH)-C(=O)R 11 ; R 5 can be represented by at least one Z 1 Substituted (C1-C6)-alkyl, H, (C3-C6)-cycloalkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl or a 4- to 6-membered oxygen-containing saturated heterocyclic ring; Z 1 is cyano, halogen, (C1-C6)-alkylthio, (C1-C6)-alkylsulfonyl, (C1-C6)-alkoxy, phenyl, pyridyl, (C1-C6)-alkoxycarbonyl, (C3-C6)-cycloalkyl, tert-butyldimethylsiloxy, OH, amino or 1,3-dioxolan-4-yl; R 6 is (C1-C6)-alkyl, (C3-C6)-cycloalkyl or benzyl which may be substituted by at least one halogen; R 7 can be represented by at least one Y 2 Substituted (C1-C6)-alkyl, H, (C1-C6)-alkoxy, (C2-C6)-alkenyl, (C2-C6)-alkynyl, -C(=O)R 6 , 3-pyridazinyl, (C2-C6)-alkenyloxy, phenoxy, benzyl, (C1-C6)-alkylsulfonyl or OH; R 8 is H, (C1-C6)-alkyl, or (C1-C6)-alkoxy; R 7 and R 8 Together with the nitrogen to which they are bound, they may form a fully saturated 4- to 6-membered ring, which may be substituted by at least one halogen, and the carbon atoms constituting the ring may be replaced by heteroatoms; Y 2 is (C1-C6)-alkoxy, (C1-C6)-alkylthio, (C1-C6)-alkoxycarbonyl, -(C=O)NH-(CH2)-C(=O)R 11 , halogen, or cyano; R 9 can be represented by at least one Z 2 Substituted (C1-C6)-alkyl, or 1-imidazolyl; Z 2 is (C1-C6)-alkoxycarbonyl; Z 3 is halogen, (C1-C6)-alkoxy, cyano, OH, (C1-C6)-alkoxycarbonyl, (C1-C6)-alkylcarbonyloxy, (C1-C6)-alkylsulfonyloxy, or -C(═O)OH; Z 4 is (C1-C6)-alkyl, (C1-C6)-alkoxymethyl, or (C1-C6)-alkoxycarbonyl; R 10 is H; R 11 is (C1-C6)-alkoxy; m is 1, 2, 3 or 4; The carbon-carbon bond in the dotted line portion is a single bond or a double bond, but the carbon-carbon bonds in two dotted line portions are not both double bonds.

2. A method for controlling or inhibiting the growth of undesirable plants by applying a difluorobutenamide compound represented by formula (I) or a salt thereof in an effective amount to harmful weeds, useful plants, or soil, In the formula, R 1 and R 2 Each is a halogen, may be replaced by at least one Y 1 Substituted (C1-C6)-chain hydrocarbon radical, (C1-C6)-alkoxy radical which may be substituted by at least one halogen, cyano radical or H; R 3 is H or fluorine atom, but excludes R 1 , R 2 and R 3 All are H cases; Y 1 is halogen, (C1-C6)-alkoxy or cyano; t is 1 or 2; R 4 -C(=O)OR 5 、-C(=O)SR 6 、-C(=O)NR 7 R 8 、-C(=O)R 9 , can be at least one Z 3 Substituted (C1-C6)-chain hydrocarbon group, -C(=O)H, -N(R 10 )C(=O)R 11 、-SR 6 、-S(=O)R 6 、-S(=O)2R 6 , =CHC(=O)R 11 , cyano, OH, 1,3-dioxolan-2-yl, 2-thiazolyl, may be replaced by at least one Z 4 Substituted 2-imidazolyl, =CHCH=CHC(=O)R 11 、-(C=O)2R 11 、-C(=NR 11 )-C(=O)R 11 or -CH(OH)-C(=O)R 11 ; R 5 can be represented by at least one Z 1 Substituted (C1-C6)-alkyl, H, (C3-C6)-cycloalkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl or a 4- to 6-membered oxygen-containing saturated heterocyclic ring; Z 1 is cyano, halogen, (C1-C6)-alkylthio, (C1-C6)-alkylsulfonyl, (C1-C6)-alkoxy, phenyl, pyridyl, (C1-C6)-alkoxycarbonyl, (C3-C6)-cycloalkyl, tert-butyldimethylsiloxy, OH, amino or 1,3-dioxolan-4-yl; R 6 is (C1-C6)-alkyl, (C3-C6)-cycloalkyl or benzyl which may be substituted by at least one halogen; R 7 can be represented by at least one Y 2 Substituted (C1-C6)-alkyl, H, (C1-C6)-alkoxy, (C2-C6)-alkenyl, (C2-C6)-alkynyl, -C(=O)R 6 , 3-pyridazinyl, (C2-C6)-alkenyloxy, phenoxy, benzyl, (C1-C6)-alkylsulfonyl or OH; R 8 is H, (C1-C6)-alkyl, or (C1-C6)-alkoxy; R 7 and R 8 Together with the nitrogen to which they are bound, they may form a fully saturated 4- to 6-membered ring, which may be substituted by at least one halogen, and the carbon atoms constituting the ring may be replaced by heteroatoms; Y 2 is (C1-C6)-alkoxy, (C1-C6)-alkylthio, (C1-C6)-alkoxycarbonyl, -(C=O)NH-(CH2)-C(=O)R 11 , halogen, or cyano; R 9 can be represented by at least one Z 2 Substituted (C1-C6)-alkyl, or 1-imidazolyl; Z 2 is (C1-C6)-alkoxycarbonyl; Z 3 is halogen, (C1-C6)-alkoxy, cyano, OH, (C1-C6)-alkoxycarbonyl, (C1-C6)-alkylcarbonyloxy, (C1-C6)-alkylsulfonyloxy, or -C(═O)OH; Z 4 is (C1-C6)-alkyl, (C1-C6)-alkoxymethyl, or (C1-C6)-alkoxycarbonyl; R 10 is H; R 11 is (C1-C6)-alkoxy; m is 1, 2, 3 or 4; The carbon-carbon bond in the dotted line portion is a single bond or a double bond, but the carbon-carbon bonds in two dotted line portions are not both double bonds.

3. A difluorobutenamide compound represented by formula (I) or a salt thereof; In the formula, R 1 and R 2 Each is a halogen, may be replaced by at least one Y 1 Substituted (C1-C6)-chain hydrocarbon radical, (C1-C6)-alkoxy radical which may be substituted by at least one halogen, cyano radical or H; R 3 is H or fluorine atom, but excludes R 1 , R 2 and R 3 All are H cases; Y 1 is halogen, (C1-C6)-alkoxy or cyano; t is 1 or 2; R 4 -C(=O)OR 5 、-C(=O)SR 6 、-C(=O)NR 7 R 8 、-C(=O)R 9 , can be at least one Z 3 Substituted (C1-C6)-chain hydrocarbon group, -C(=O)H, -N(R 10 )C(=O)R 11 、-SR 6 、-S(=O)R 6 、-S(=O)2R 6 , =CHC(=O)R 11 , cyano, OH, 1,3-dioxolan-2-yl, 2-thiazolyl, may be replaced by at least one Z 4 Substituted 2-imidazolyl, =CHCH=CHC(=O)R 11 、-(C=O)2R 11 、-C(=NR 11 )-C(=O)R 11 or -CH(OH)-C(=O)R 11 ; R 5 can be represented by at least one Z 1 Substituted (C1-C6)-alkyl, H, (C3-C6)-cycloalkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl or a 4- to 6-membered oxygen-containing saturated heterocyclic ring; Z 1 is cyano, halogen, (C1-C6)-alkylthio, (C1-C6)-alkylsulfonyl, (C1-C6)-alkoxy, phenyl, pyridyl, (C1-C6)-alkoxycarbonyl, (C3-C6)-cycloalkyl, tert-butyldimethylsiloxy, OH, amino or 1,3-dioxolan-4-yl; R 6 is (C1-C6)-alkyl, (C3-C6)-cycloalkyl or benzyl which may be substituted by at least one halogen; R 7 can be represented by at least one Y 2 Substituted (C1-C6)-alkyl, H, (C1-C6)-alkoxy, (C2-C6)-alkenyl, (C2-C6)-alkynyl, -C(=O)R 6 , 3-pyridazinyl, (C2-C6)-alkenyloxy, phenoxy, benzyl, (C1-C6)-alkylsulfonyl or OH; R 8 is H, (C1-C6)-alkyl, or (C1-C6)-alkoxy; R 7 and R 8 Together with the nitrogen to which they are bound, they may form a fully saturated 4- to 6-membered ring, which may be substituted by at least one halogen, and the carbon atoms constituting the ring may be replaced by heteroatoms; Y 2 is (C1-C6)-alkoxy, (C1-C6)-alkylthio, (C1-C6)-alkoxycarbonyl, -(C=O)NH-(CH2)-C(=O)R 11 , halogen, or cyano; R 9 can be represented by at least one Z 2 Substituted (C1-C6)-alkyl, or 1-imidazolyl; Z 2 is (C1-C6)-alkoxycarbonyl; Z 3 is halogen, (C1-C6)-alkoxy, cyano, OH, (C1-C6)-alkoxycarbonyl, (C1-C6)-alkylcarbonyloxy, (C1-C6)-alkylsulfonyloxy, or -C(═O)OH; Z 4 is (C1-C6)-alkyl, (C1-C6)-alkoxymethyl, or (C1-C6)-alkoxycarbonyl; R 10 is H; R 11 is (C1-C6)-alkoxy; m is 1, 2, 3 or 4; The carbon-carbon bond in the dotted line portion is a single bond or a double bond, but the carbon-carbon bonds in two dotted line portions are not both double bonds.

4. The difluorobutenamide compound or a salt thereof according to claim 3, wherein R 4 -C(=O)OR 5 、-C(=O)SR 6 、-C(=O)NR 7 R 8 、-C(=O)R 9 , can be at least one Z 3 Substituted (C1-C6)-chain hydrocarbon group, or -CH(OH)-C(=O)R 11 , R 7 can be represented by at least one Y 2 Substituted (C1-C6)-alkyl, H, or (C1-C6)-alkoxy, Z 3 It is (C1-C6)-alkoxycarbonyl, or -C(=O)OH.

5. The difluorobutylene amide compound or a salt thereof according to claim 3, wherein R 1 and R 2 Each is a halogen, may be replaced by at least one Y 1 Substituted (C1-C6)-alkyl, (C1-C6)-alkoxy which may be substituted with at least one halogen, cyano or H, Y 1 is halogen, R 4 -C(=O)OR 5 、-C(=O)SR 6 、-C(=O)NR 7 R 8 、-C(=O)R 9 , can be at least one Z 3 Substituted (C1-C6)-chain hydrocarbon group, or -CH(OH)-C(=O)R 11 , R 7 can be represented by at least one Y 2 Substituted (C1-C6)-alkyl, H, or (C1-C6)-alkoxy, Z 3 It is (C1-C6)-alkoxycarbonyl, or -C(=O)OH.

6. The difluorobutenamide compound or its salt according to claim 3, wherein R 1 and R 2 Each is a halogen, may be replaced by at least one Y 1 Substituted (C1-C6)-alkyl, (C1-C6)-alkoxy which may be substituted with at least one halogen, cyano or H, Y 1 is halogen, R 4 -C(=O)OR 5 、-C(=O)SR 6 、-C(=O)NR 7 R 8 or -CH(OH)-C(=O)R 11 , R 7 can be represented by at least one Y 2 Substituted (C1-C6)-alkyl, H, or (C1-C6)-alkoxy, Z 1 is cyano, halogen, (C1-C6)-alkylthio, (C1-C6)-alkylsulfonyl, (C1-C6)-alkoxy, or 1,3-dioxolan-4-yl, R 6 is a (C1-C6)-alkyl group which may be substituted with at least one halogen, R 7 can be represented by at least one Y 2 Substituted (C1-C6)-alkyl, H, or (C1-C6)-alkoxy, R 8 is H, or (C1-C6)-alkyl, Y 2 is (C1-C6)-alkoxy, halogen, or cyano. 7 . The difluorobutenamide compound or a salt thereof according to claim 3 , wherein m is 1 or 2.

8. A herbicidal composition comprising the difluorocrotonamide compound or a salt thereof according to any one of claims 4 to 6 as an active ingredient.

9. A method for controlling undesirable plants or inhibiting their growth, comprising applying an effective amount of the difluorocrotonamide compound or a salt thereof according to any one of claims 4 to 6 to harmful weeds, useful plants, or soil.

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