Herbicide composition comprising nicotinamide compounds and safeners

Abstract

The present application relates to a herbicide composition comprising a nicotinamide compound or an agriculturally acceptable salt thereof and a safener, and to a weed control method using same. If the herbicide composition of the present application is used, it is possible to reduce damage to useful crops when using a nicotinamide compound having excellent herbicidal activity.

Description

Herbicidal composition comprising a nicotinamide compound and a laxative

[0001] Cross-citation with related application(s)

[0002] This application claims the benefit of priority from Republic of Korea Patent Application No. 10-2024-0046781, dated April 5, 2024, the entire contents of which are incorporated herein by reference.

[0003] Numerous papers and patents are referenced and cited throughout this application. The disclosures of these cited papers and patents are incorporated herein by reference in their entirety to provide a clearer understanding of the state of the art and the scope of the present invention.

[0004] The present application relates to a herbicidal composition comprising a nicotinamide compound or an agrochemically acceptable salt thereof and a herbicidal reducer, and a weed control method using the same. The present application provides a technique for reducing herbicidal damage to useful crops when using a nicotinamide compound with excellent herbicidal activity.

[0005]

[0006] Weed control is generally crucial for improving agricultural productivity, and various types of herbicides have been used over the years. For example, triazine herbicides, such as atrazine, or anilide herbicides, such as alachlor or metolachlor, have been used in corn cultivation. Meanwhile, non-selective herbicides, such as paraquat and glyphosate, have been used. However, many weeds still cause damage to agriculture, and many existing herbicides have developed resistance, rendering them less effective. Therefore, research into new herbicides is ongoing, but the toxicity of these herbicides poses a problem, as they can harm not only the target weeds but also the crops.

[0007] To protect useful crops from herbicide toxicity, safeners can be used in conjunction with herbicides. Safeners are chemicals that protect crops from the negative effects of specific herbicides, effectively controlling undesirable plants like weeds without harming the crop. However, safeners exhibit varying responses depending on the herbicide, crop, and dosage applied. Therefore, the conditions for effective safener use to mitigate harm have not been established.

[0008] Therefore, research is needed on technologies that can protect useful crops from damage while using novel herbicides to control herbicide-resistant weeds.

[0009]

[0010] [Prior Art Literature]

[0011] [Patent Document]

[0012] (Patent Document 1) Republic of Korea Publication Patent No. 10-2008-0033992

[0013] The present inventors have developed a novel nicotinamide compound or an agrochemically acceptable salt thereof with excellent herbicidal activity, and have diligently studied ways to reduce the phytotoxicity of the compound to useful crops when used. As a result, they have discovered that when a nicotinamide compound or an agrochemically acceptable salt thereof is mixed with a phytotoxicity reducer, the phytotoxicity of useful crops is reduced, thereby completing the present invention.

[0014] Accordingly, the purpose of the present application is to provide a herbicidal composition comprising a nicotinamide compound or an agrochemically acceptable salt thereof and a laxative.

[0015] Another object of the present application is to provide a composition comprising a nicotinamide compound or an agrochemically acceptable salt thereof and a laxative as a herbicide and / or for controlling weeds.

[0016] Another object of the present application is to provide a use for the preparation of a herbicidal composition comprising a nicotinamide compound or an agrochemically acceptable salt thereof and a laxative.

[0017] Another object of the present application is to provide a method for preparing a herbicidal composition, comprising a step of mixing a nicotinamide compound or an agrochemically acceptable salt thereof and a laxative.

[0018] Another object of the present application is to provide a method for controlling weeds in a cultivated field, comprising the step of applying an effective amount of the herbicidal composition described above to the cultivated field.

[0019] Another object of the present application is to provide a method for controlling weeds in a cultivated field, comprising the step of treating the cultivated field together with the nicotinamide compound or an agrochemically acceptable salt thereof and a phytoprotector.

[0020]

[0021] Each description and embodiment disclosed in this specification may also be applied to each other description and embodiment. That is, all combinations of the various elements disclosed in this specification fall within the scope of this application. Furthermore, the scope of this application is not limited by the specific descriptions described below.

[0022] Below, it is explained in more detail.

[0023]

[0024] According to one aspect of the present application, the present application comprises a nicotinamide compound represented by the following chemical formula 1 or an agrochemically acceptable salt thereof.

[0025] [Chemical Formula 1]

[0026] ; and

[0027] Provided is a herbicidal composition additionally comprising at least one laxative selected from the group consisting of isoxadifen-ethyl, benoxacor, dichlormid, and mefenpyr-diethyl.

[0028] In the above chemical formula 1,

[0029] A is or represents;

[0030] B is or represents;

[0031] X represents O or S;

[0032] Y represents O, S, SO, SO2, NH, N-(C1-C6)-alkyl group, N-(C2-C6)-alkenyl group, N-(C2-C6)-alkynyl group, NO-(C1-C6)-alkyl group, NS-(C1-C6)-alkyl group, NS(O)-(C1-C6)-alkyl group, N-SO2-(C1-C6)-alkyl group, NO-(C1-C3)-alkyl-aryl group or hydroxylamino group;

[0033] Z represents N or C-R8;

[0034] R1 represents a (C1-C6)-alkyl group, a (C1-C6)-haloalkyl group, a (C2-C6)-alkenyl group, a (C2-C6)-haloalkenyl group, a (C2-C6)-alkynyl group, a (C2-C6)-haloalkynyl group, a (C3-C6)-cycloalkyl group or a (C3-C6)-halocycloalkyl group;

[0035] R2 represents hydrogen, a (C1-C6)-alkyl group, a (C1-C6)-haloalkyl group, a (C2-C6)-alkenyl group, a (C2-C6)-haloalkenyl group, a (C2-C6)-alkynyl group, a (C2-C6)-haloalkynyl group, a C(O)-( C1-C6)-alkyl group, a C(O)aryl group, a C(O)heteroaryl group, or a SO2-(C1-C6)-alkyl group;

[0036] R3 and R4 each independently represent hydrogen, a halogen group, a (C1-C6)-alkyl group, a (C2-C6)-alkenyl group, or a (C3-C6)-cycloalkyl group;

[0037] R5 represents a halogen group, a (C1-C3)-alkyl group or a (C1-C3)-haloalkyl group;

[0038] R6 represents a (C1-C6)-alkyl group, a (C1-C6)-haloalkyl group, a (C2-C6)-alkenyl group, a (C2-C6)-haloalkenyl group, a (C2-C6)-alkynyl group, a (C2-C6)-haloalkynyl group, a (C3-C6)-cycloalkyl group, a (C3-C6)-halocycloalkyl group, a (C1-C3)-alkyl-O-(C1-C3)-alkyl group or a (C1-C3)-alkyl-S-(C1-C3)-alkyl group;

[0039] R7 represents a (C1-C6)-alkyl group, a (C1-C6)-haloalkyl group, a (C3-C6)-cycloalkyl group or a (C3-C6)-halocycloalkyl group;

[0040] R8 is hydrogen, (C1-C6)-alkyl group, (C1-C6)-haloalkyl group, (C2-C6)-alkenyl group, (C2-C6)-haloalkenyl group, (C2-C6)-alkynyl group, (C2-C6)-haloalkynyl group, (C3-C6)-cycloalkyl group, (C3-C6)-halocycloalkyl group, (C1-C6)-alkoxy group, (C1-C6)-haloalkoxy group, (C1-C6)-alkylthio group, (C1-C6)-haloalkylthio group, S(O)-(C1-C6)-alkyl group, S(O)-(C1-C6)-haloalkyl group, SO2-(C1-C6)-alkyl group, SO2-(C1-C6)-haloalkyl group, NR9R 10 , representing a cyano group or a halogen group;

[0041] R9 or R 10 independently represents hydrogen, a (C1-C3)-alkyl group or a (C1-C3)-haloalkyl group;

[0042] n and m each independently represent 0, 1, or 2.

[0043] In one implementation example,

[0044] The above A is or represents;

[0045] The above B is or represents;

[0046] wherein X represents O or S;

[0047] The above Y represents O, S, SO, SO2, NH, N-(C1-C3)-alkyl group, N-(C2-C6)-alkynyl group, NO-(C1-C3)-alkyl group, NO-(C1-C3)-alkyl-aryl group or hydroxylamino group;

[0048] wherein Z represents N or C-R8;

[0049] The above R1 represents a (C1-C6)-alkyl group, a (C1-C6)-haloalkyl group, a (C2-C6)-alkenyl group or a (C2-C6)-alkynyl group;

[0050] The above R2 represents hydrogen, a (C1-C3)-alkyl group, a (C1-C3)-haloalkyl group, a C(O)-(C1-C6)-alkyl group, a C(O)aryl group, or a SO2-(C1-C3)-alkyl group;

[0051] The above R3 and R4 each independently represent hydrogen, a halogen group, a (C1-C6)-alkyl group or a (C2-C6)-alkenyl group;

[0052] The above R5 represents a halogen group or a (C1-C3)-haloalkyl group;

[0053] The above R6 represents a (C1-C6)-alkyl group, a (C1-C6)-haloalkyl group or a (C1-C3)-alkyl-O-(C1-C3)-alkyl group;

[0054] The above R7 represents a (C1-C6)-alkyl group or a (C3-C6)-cycloalkyl group;

[0055] The above R8 is hydrogen, (C1-C3)-alkyl group, (C1-C6)-haloalkyl group, (C2-C6)-alkenyl group, (C1-C3)-alkoxy group, (C1-C3)-haloalkoxy group, (C1-C3)-alkylthio group, SO2-(C1-C3)-alkyl group, NR9R 10 , representing a cyano group or a halogen group;

[0056] The above R 9　 or R 10 independently represents hydrogen or a (C1-C3)-alkyl group;

[0057] wherein n represents 0 or 1;

[0058] The above m can represent 0, 1 or 2.

[0059] In one implementation example,

[0060] The above A is or represents;

[0061] The above B is or represents;

[0062] wherein X represents O or S;

[0063] The above Y represents O, S, SO, SO2, NH, a methylamino group, an ethylamino group, a propargylamino group, a benzyloxyamino group, a methoxyamino group, an ethoxyamino group or a hydroxylamino group;

[0064] wherein Z represents N or C-R8;

[0065] The above R1 represents a methyl group, an ethyl group, an n-propyl group, a difluoromethyl group, an allyl group or a propargyl group;

[0066] The above R2 represents hydrogen, a methyl group, an acetyl group, a benzoyl group, or a methanesulfonyl group;

[0067] The above R3 and R4 each independently represent hydrogen, chlorine, bromine, iodine, a methyl group, an ethyl group or a vinyl group;

[0068] The above R5 represents chlorine, difluoromethyl group, trifluoromethyl group, chlorodifluoromethyl group or perfluoroethyl group;

[0069] The above R6 represents a methyl group, an ethyl group, a difluoromethyl group or a methoxymethyl group;

[0070] The above R7 represents a methyl group, an ethyl group, an isopropyl group or a cyclohexyl group;

[0071] The above R8 represents hydrogen, a methyl group, a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, an ethenyl group, a methylethenyl group, a methoxy group, a trifluoroethoxy group, a methylthio group, a methanesulfonyl group, a dimethylamino group, a cyano group, chlorine, bromine or iodine;

[0072] wherein n represents 0 or 1;

[0073] The above m can represent 0, 1 or 2.

[0074] In one embodiment, the nicotinamide compound or agrochemically acceptable salt thereof may be selected from the group consisting of:

[0075] (1)N-(1-methyl-1H-tetrazol-5-yl)-2-((1-methyl-1H-tetrazol-5-yl)methoxy)-6-(trifluoromethyl)nicotinamide;

[0076] (2)N-(1-(difluoromethyl)-1H-tetrazol-5-yl)-2-((1-methyl-1H-tetrazol-5-yl)methoxy)-6-(trifluoromethyl)nicotinamide;

[0077] (3) 2-((1-(difluoromethyl)-1H-tetrazol-5-yl)methoxy)-N-methyl-N-(1-methyl-1H-tetrazol-5-yl)-6-(trifluoromethyl)nicotinamide;

[0078] (4) 4-chloro-N-(1-methyl-1H-tetrazol-5-yl)-2-((1-methyl-1H-tetrazol-5-yl)methoxy)-6-(trifluoromethyl)nicotinamide;

[0079] (5) 5-methyl-N-(1-methyl-1H-tetrazol-5-yl)-2-((1-methyl-1H-tetrazol-5-yl)methoxy)-6-(trifluoromethyl)nicotinamide;

[0080] (6)N-(1-methyl-1H-tetrazol-5-yl)-2-((1-methyl-1H-tetrazol-5-yl)methoxy)-6-(trifluoromethyl)-5-vinylnicotinamide;

[0081] (7) 5-ethyl-N-(1-methyl-1H-tetrazol-5-yl)-2-((1-methyl-1H-tetrazol-5-yl)methoxy)-6-(trifluoromethyl)nicotinamide;

[0082] (8) 6-chloro-N-(1-methyl-1H-tetrazol-5-yl)-2-((1-methyl-1H-tetrazol-5-yl)methoxy)nicotinamide;

[0083] (9) 2-((1-(difluoromethyl)-1H-tetrazol-5-yl)methoxy)-N-(1-methyl-1H-tetrazol-5-yl)-6-(trifluoromethyl)nicotinamide;

[0084] (10) 2-(methyl((1-methyl-1H-tetrazol-5-yl)methyl)amino)-N-(1-methyl-1H-tetrazol-5-yl)-6-(trifluoromethyl)nicotinamide;

[0085] (11)N-(1-methyl-1H-tetrazol-5-yl)-2-((1-methyl-1H-tetrazol-5-yl)thio)-6-(trifluoromethyl)nicotinamide;

[0086] (12)N-(1-methyl-1H-tetrazol-5-yl)-2-((1-methyl-1H-tetrazol-5-yl)methoxy)-6-(trifluoromethyl)pyridine-3-carbothioamide;

[0087] (13) 2-((1-methyl-1H-1,2,4-triazol-5-yl)methoxy)-N-(1-methyl-1H-tetrazol-5-yl)-6-(trifluoromethyl)nicotinamide;

[0088] (14)N-(1-methyl-1H-tetrazol-5-yl)-2-(((1-methyl-1H-tetrazol-5-yl)methoxy)methyl)-6-(trifluoromethyl)nicotinamide;

[0089] (15) 2-(((1-(difluoromethyl)-1H-tetrazol-5-yl)methoxy)methyl)-N-(1-methyl-1H-tetrazol-5-yl)-6-(trifluoromethyl)nicotinamide;

[0090] (16) 2-((methyl((1-methyl-1H-tetrazol-5-yl)methyl)amino)-N-((1-methyl-1H-tetrazol-5-yl)-6-(trifluoromethyl)nicotinamide;

[0091] (17) 2-((methoxy((1-methyl-1H-1,2,4-triazol-5-yl)methyl)amino)methyl)-N-(1-methyl-1H-tetrazol-5-yl)-6-(trifluoromethyl)nicotinamide;

[0092] (18)N-(1-methyl-1H-tetrazol-5-yl)-2-(((1-methyl-1H-tetrazol-5-yl)thio)methyl)-6-(trifluoromethyl)nicotinamide;

[0093] (19) 2-(((1-methyl-1H-1,2,4-triazol-5-yl)methoxy)methyl)-N-(1-methyl-1H-tetrazol-5-yl)-6-(trifluoromethyl)nicotinamide;

[0094] (20)N-(1-methyl-1H-tetrazol-5-yl)-2-(((1-methyl-1H-tetrazol-5-yl)oxy)methyl)-6-(trifluoromethyl)nicotinamide;

[0095] (21)N-(1-methyl-1H-tetrazol-5-yl)-2-((2-methyl-2H-tetrazol-5-yl)methoxy)-6-(trifluoromethyl)nicotinamide;

[0096] (22) 2-(methyl((2-methyl-2H-tetrazol-5-yl)methyl)amino)-N-(1-methyl-1H-tetrazol-5-yl)-6-(trifluoromethyl)nicotinamide;

[0097] (23) 2-(ethyl((2-methyl-2H-tetrazol-5-yl)methyl)amino)-N-(1-methyl-1H-tetrazol-5-yl)-6-(trifluoromethyl)nicotinamide;

[0098] (24)N-(1-methyl-1H-tetrazol-5-yl)-2-(((2-methyl-2H-tetrazol-5-yl)methyl)(prop-2-yn-1-yl)amino)-6-(trifluoromethyl)nicotinamide;

[0099] (25) 2-((benzyloxy)((2-methyl-2H-tetrazol-5-yl)methyl)amino)-N-(1-methyl-1H-tetrazol-5-yl)-6-(trifluoromethyl)nicotinamide;

[0100] (26) 2-(methoxy((2-methyl-2H-tetrazol-5-yl)methyl)amino)-N-(1-methyl-1H-tetrazol-5-yl)-6-(trifluoromethyl)nicotinamide;

[0101] (27) 2-(Ethoxy((2-methyl-2H-tetrazol-5-yl)methyl)amino)-N-(1-methyl-1H-tetrazol-5-yl)-6-(trifluoromethyl)nicotinamide;

[0102] (28)N-(1-methyl-1H-tetrazol-5-yl)-2-(((2-methyl-2H-tetrazol-5-yl)methyl)amino)-6-(trifluoromethyl)nicotinamide;

[0103] (29) 2-(hydroxy((2-methyl-2H-tetrazol-5-yl)methyl)amino)-N-(1-methyl-1H-tetrazol-5-yl)-6-(trifluoromethyl)nicotinamide;

[0104] (30) 2-(methyl((1-methyl-1H-1,2,4-triazol-3-yl)methyl)amino)-N-(1-methyl-1H-tetrazol-5-yl)-6-(trifluoromethyl)nicotinamide;

[0105] (31) 2-(methyl(2-(2-methyl-2H-tetrazol-5-yl)ethyl)amino)-N-(1-methyl-1H-tetrazol-5-yl)-6-(trifluoromethyl)nicotinamide;

[0106] (32) 2-((1-methyl-1H-1,2,4-triazol-3-yl)methoxy)-N-(1-methyl-1H-tetrazol-5-yl)-6-(trifluoromethyl)nicotinamide;

[0107] (33)N-(1-methyl-1H-tetrazol-5-yl)-2-(((2-methyl-2H-tetrazol-5-yl)methoxy)methyl)-6-(trifluoromethyl)nicotinamide;

[0108] (34)N-acetyl-N-(1-methyl-1H-tetrazol-5-yl)-2-(((2-methyl-2H-tetrazol-5-yl)methoxy)methyl)-6-(trifluoromethyl)nicotinamide;

[0109] (35)N-Benzoyl-N-(1-methyl-1H-tetrazol-5-yl)-2-(((2-methyl-2H-tetrazol-5-yl)methoxy)methyl)-6-(trifluoromethyl)nicotinamide;

[0110] (36)N-(1-methyl-1H-tetrazol-5-yl)-2-(((2-methyl-2H-tetrazol-5-yl)methoxy)methyl)-N-(methylsulfonyl)-6-(trifluoromethyl)nicotinamide;

[0111] (37) 6-(Chlorodifluoromethyl)-N-(1-methyl-1H-tetrazol-5-yl)-2-(((2-methyl-2H-tetrazol-5-yl)methoxy)methyl)nicotinamide;

[0112] (38) 6-(Chlorodifluoromethyl)-2-((methoxy((2-methyl-2H-tetrazol-5-yl)methyl)amino)methyl)-N-(1-methyl-1H-tetrazol-5-yl)nicotinamide;

[0113] (39) 6-(Chlorodifluoromethyl)-2-(((1-methyl-1H-1,2,4-triazol-3-yl)methoxy)methyl)-N-(1-methyl-1H-tetrazol-5-yl)nicotinamide;

[0114] (40)N-(1-methyl-1H-tetrazol-5-yl)-2-(((2-methyl-2H-tetrazol-5-yl)methoxy)methyl)-6-(perfluoroethyl)nicotinamide;

[0115] (41) 2-(((1-methyl-1H-1,2,4-triazol-3-yl)methoxy)methyl)-N-(1-methyl-1H-tetrazol-5-yl)-6-(perfluoroethyl)nicotinamide;

[0116] (42) 6-(Difluoromethyl)-N-(1-methyl-1H-tetrazol-5-yl)-2-(((2-methyl-2H-tetrazol-5-yl)methoxy)methyl)nicotinamide;

[0117] (43) 6-(Difluoromethyl)-2-(((1-methyl-1H-1,2,4-triazol-3-yl)methoxy)methyl)-N-((1-methyl-1H-tetrazol-5-yl)nicotinamide;

[0118] (44) 6-(Difluoromethyl)-2-((methoxy((2-methyl-2H-tetrazol-5-yl)methyl)amino)methyl)-N-(1-methyl-1H-tetrazol-5-yl)nicotinamide;

[0119] (45) 2-(((2-ethyl-2H-tetrazol-5-yl)methoxy)methyl)-N-(1-methyl-1H-tetrazol-5-yl)-6-(trifluoromethyl)nicotinamide;

[0120] (46)N-(1-ethyl-1H-tetrazol-5-yl)-2-(((2-ethyl-2H-tetrazol-5-yl)methoxy)methyl)-6-(trifluoromethyl)nicotinamide;

[0121] (47) 2-(((2-ethyl-2H-tetrazol-5-yl)methoxy)methyl)-N-(1-n-propyl-1H-tetrazol-5-yl)-6-(trifluoromethyl)nicotinamide;

[0122] (48)N-(1-allyl-1H-tetrazol-5-yl)-2-(((2-ethyl-2H-tetrazol-5-yl)methoxy)methyl)-6-(trifluoromethyl)nicotinamide;

[0123] (49) 2-(((2-(methoxymethyl)-2H-tetrazol-5-yl)methoxy)methyl)-N-(1-methyl-1H-tetrazol-5-yl)-6-(trifluoromethyl)nicotinamide;

[0124] (50) 2-(((2-(difluoromethyl)-2H-tetrazol-5-yl)methoxy)methyl)-N-(1-methyl-1H-tetrazol-5-yl)-6-(trifluoromethyl)nicotinamide;

[0125] (51) 2-((methyl((2-methyl-2H-tetrazol-5-yl)methyl)amino)methyl)-N-(1-methyl-1H-tetrazol-5-yl)-6-(trifluoromethyl)nicotinamide;

[0126] (52) 2-((ethyl((2-methyl-2H-tetrazol-5-yl)methyl)amino)methyl)-N-(1-methyl-1H-tetrazol-5-yl)-6-(trifluoromethyl)nicotinamide;

[0127] (53) 2-((methoxy((2-methyl-2H-tetrazol-5-yl)methyl)amino)methyl)-N-(1-methyl-1H-tetrazol-5-yl)-6-(trifluoromethyl)nicotinamide;

[0128] (54)N-(1-methyl-1H-tetrazol-5-yl)-2-((((2-methyl-2H-tetrazol-5-yl)methyl)thio)methyl)-6-(trifluoromethyl)nicotinamide;

[0129] (55)N-(1-methyl-1H-tetrazol-5-yl)-2-((((2-methyl-2H-tetrazol-5-yl)methyl)sulfinyl)methyl)-6-(trifluoromethyl)nicotinamide;

[0130] (56)N-(1-methyl-1H-tetrazol-5-yl)-2-((((2-methyl-2H-tetrazol-5-yl)methyl)sulfonyl)methyl)-6-(trifluoromethyl)nicotinamide;

[0131] (57)N-(1-methyl-1H-tetrazol-5-yl)-2-(((2-methyl-2H-tetrazol-5-yl)methoxy)methyl)-6-(trifluoromethyl)pyridine-3-carbothioamide;

[0132] (58)N-(1-methyl-1H-tetrazol-5-yl)-2-((((2-methyl-2H-tetrazol-5-yl)methyl)thio)methyl)-6-(trifluoromethyl)pyridine-3-carbothioamide;

[0133] (59) 6-(Difluoromethyl)-N-(1-methyl-1H-tetrazol-5-yl)-2-((((2-methyl-2H-tetrazol-5-yl)methyl)thio)methyl)nicotinamide;

[0134] (60)N-Benzoyl-N-(1-methyl-1H-tetrazol-5-yl)-2-((((2-methyl-2H-tetrazol-5-yl)methyl)thio)methyl)-6-(trifluoromethyl)nicotinamide;

[0135] (61)N-(1-methyl-1H-tetrazol-5-yl)-2-((((2-methyl-2H-tetrazol-5-yl)methyl)thio)methyl)-N-(methylsulfonyl)-6-(trifluoromethyl)nicotinamide;

[0136] (62) 6-(Difluoromethyl)-N-(1-methyl-1H-tetrazol-1-yl)-2-((((2-methyl-2H-tetrazol-5-yl)methyl)sulfinyl)methyl)nicotinamide;

[0137] (63)N-Benzoyl-6-(difluoromethyl)-N-(1-methyl-1H-tetrazol-5-yl)-2-((((2-methyl-2H-tetrazol-5-yl)methyl)thio)methyl)nicotinamide (Compound No. 2-112);

[0138] (64) 2-(((1-methyl-1H-1,2,4-triazol-3-yl)methoxy)methyl)-N-(1-methyl-1H-tetrazol-5-yl)-6-(trifluoromethyl)nicotinamide;

[0139] (65) 2-(((1-methyl-1H-1,2,4-triazol-3-yl)methoxy)methyl)-N-(1-n-propyl-1H-tetrazol-5-yl)-6-(trifluoromethyl)nicotinamide;

[0140] (66)N-(1-allyl-1H-tetrazol-5-yl)-2-(((1-methyl-1H-1,2,4-triazol-3-yl)methoxy)methyl)-6-(trifluoromethyl)nicotinamide;

[0141] (67) 2-(((1,5-dimethyl-1H-1,2,4-triazol-3-yl)methoxy)methyl)-N-(1-methyl-1H-tetrazol-5-yl)-6-(trifluoromethyl)nicotinamide;

[0142] (68) 2-(((1,5-dimethyl-1H-1,2,4-triazol-3-yl)methoxy)methyl)-N-(1-methyl-1H-tetrazol-5-yl)-6-(trifluoromethyl)pyridine-3-carbothioamide;

[0143] (69)N-(1-methyl-1H-tetrazol-5-yl)-2-(((1-methyl-5-(trifluoromethyl)-1H-1,2,4-triazol-3-yl)methoxy)methyl)-6-(trifluoromethyl)nicotinamide;

[0144] (70)N-(1-ethyl-1H-tetrazol-5-yl)-2-(((1-methyl-5-(trifluoromethyl)-1H-1,2,4-triazol-3-yl)methoxy)methyl)-6-(trifluoromethyl)nicotinamide;

[0145] (71) 2-(((1-methyl-5-(trifluoromethyl)-1H-1,2,4-triazol-3-yl)methoxy)methyl)-N-(1-propyl-1H-tetrazol-5-yl)-6-(trifluoromethyl)nicotinamide;

[0146] (72)N-(1-allyl-1H-tetrazol-5-yl)-2-(((1-methyl-5-(trifluoromethyl)-1H-1,2,4-triazol-3-yl)methoxy)methyl)-6-(trifluoromethyl)nicotinamide;

[0147] (73) 2-(((1-methyl-5-(trifluoromethyl)-1H-1,2,4-triazol-3-yl)methoxy)methyl)-N-(1-prop-2-yn-1-yl)-1H-tetrazol-5-yl)-6-(trifluoromethyl)nicotinamide;

[0148] (74) 2-(((5-(difluoromethyl)-1-methyl-1H-1,2,4-triazol-3-yl)methoxy)methyl)-N-(1-methyl-1H-tetrazol-5-yl)-6-(trifluoromethyl)nicotinamide;

[0149] (75) 2-(((5-(difluoromethyl)-1-methyl-1H-1,2,4-triazol-3-yl)-methoxy)-N-(1-n-propyl-1H-tetrazol-5-yl)-6-(trifluoromethyl)nicotinamide;

[0150] (76)N-(1-allyl-1H-tetrazol-5-yl)-2-(((5-(difluoromethyl)-1-methyl-1H-1,2,4-triazol-3-yl)methoxy)methyl)-6-(trifluoromethyl)nicotinamide;

[0151] (77) 2-(((5-(fluoromethyl)-1-methyl-1H-1,2,4-triazol-3-yl)methoxy)methyl)-N-(1-methyl-1H-tetrazol-5-yl)-6-(trifluoromethyl)nicotinamide;

[0152] (78)N-(1-methyl-1H-tetrazol-5-yl)-2-(((1-methyl-5-vinyl-1H-1,2,4-triazol-3-yl)methoxy)methyl)-6-(trifluoromethyl)nicotinamide;

[0153] (79)N-(1-methyl-1H-tetrazol-5-yl)-2-(((1-methyl-5-(prop-1-en-2-yl)-1H-1,2,4-triazol-3-yl)methoxy)methyl)-6-(trifluoromethyl)nicotinamide;

[0154] (80) 2-(((5-methoxy-1-methyl-1H-1,2,4-triazol-3-yl)methoxy)methyl)-N-(1-methyl-1H-tetrazol-5-yl)-6-(trifluoromethyl)nicotinamide;

[0155] (81)N-(1-methyl-1H-tetrazol-5-yl)-2-(((1-methyl-5-(2,2,2-trifluoroethoxy)-1H-1,2,4-triazol-3-yl)methoxy)methyl)-6-(trifluoromethyl)nicotinamide;

[0156] (82)N-(1-methyl-1H-tetrazol-5-yl)-2-(((1-methyl-5-(methylthio)-1H-1,2,4-triazol-3-yl)methoxy)methyl)-6-(trifluoromethyl)nicotinamide;

[0157] (83)N-(1-methyl-1H-tetrazol-5-yl)-2-(((1-methyl-5-(methylsulfonyl)-1H-1,2,4-triazol-3-yl)methoxy)methyl)-6-(trifluoromethyl)nicotinamide;

[0158] (84) 2-(((5-(dimethylamino)-1-methyl-1H-1,2,4-triazol-3-yl)methoxy)methyl)-N-(1-methyl-1H-tetrazol-5-yl)-6-(trifluoromethyl)nicotinamide;

[0159] (85) 2-(((5-cyano-1-methyl-1H-1,2,4-triazol-3-yl)methoxy)methyl)-N-(1-methyl-1H-tetrazol-5-yl)-6-(trifluoromethyl)nicotinamide;

[0160] (86) 2-(((5-chloro-1-methyl-1H-1,2,4-triazol-3-yl)methoxy)methyl)-N-(1-methyl-1H-tetrazol-5-yl)-6-(trifluoromethyl)nicotinamide;

[0161] (87) 2-(((5-Bromo-1-methyl-1H-1,2,4-triazol-3-yl)methoxy)methyl)-N-(1-methyl-1H-tetrazol-5-yl)-6-(trifluoromethyl)nicotinamide;

[0162] (88) 2-(((5-Iodo-1-methyl-1H-1,2,4-triazol-3-yl)methoxy)methyl-N-(1-methyl-1H-tetrazol-5-yl)-6-(trifluoromethyl)nicotinamide;

[0163] (89) Methyl (1-(2-(((1-methyl-1H-1,2,4-triazol-3-yl)methoxy)methyl)-N-(1-methyl-1H-tetrazol-5-yl)-6-(trifluoromethyl)nicotinamido)ethyl)carbonate;

[0164] (90) Methyl (1-(N-(1-methyl-1H-tetrazol-5-yl)-2-(((2-methyl-2H-tetrazol-5-yl)methoxy)methyl)-6-(trifluoromethyl)pyridine-3-carbothioamido)ethyl)carbonate;

[0165] (91) Methyl (1-(N-(1-methyl-1H-tetrazol-5-yl)-2-((((2-methyl-2H-tetrazol-5-yl)methyl)thio)methyl)-6-(trifluoromethyl)nicotinamido)ethyl)carbonate;

[0166] (92) Methyl (1-(N-(1-methyl-1H-tetrazol-5-yl)-2-(((2-methyl-2H-tetrazol-5-yl)methoxy)methyl)-6-(trifluoromethyl)nicotinamido)ethyl)carbonate;

[0167] (93) Ethyl(1-(N-(1-methyl-1H-tetrazol-5-yl)-2-(((2-methyl-2H-tetrazol-5-yl)methoxy)methyl)-6-(trifluoromethyl)nicotinamido)ethyl)carbonate;

[0168] (94) Ethyl (1-(N-(1-methyl-1H-tetrazol-5-yl)-2-((((2-methyl-2H-tetrazol-5-yl)methyl)thio)methyl)-6-(trifluoromethyl)pyridine-3-carbothioamido)ethyl)carbonate;

[0169] (95) Ethyl (1-(4-methyl-5-((2-((((2-methyl-2H-tetrazol-5-yl)methyl)thio)methyl)-6-(trifluoromethyl)nicotinoyl)imino)-4,5-dihydro-1H-tetrazol-1-yl)ethyl)carbonate;

[0170] (96) Cyclohexyl(1-(N-(1-methyl-1H-tetrazol-5-yl)-2-(((2-methyl-2H-tetrazol-5-yl)methoxy)methyl)-6-(trifluoromethyl)nicotinamido)ethyl)carbonate;

[0171] (97) isopropyl(1-(N-(1-methyl-1H-tetrazol-5-yl)-2-(((2-methyl-2H-tetrazol-5-yl)methoxy)methyl)-6-(trifluoromethyl)nicotinamido)ethyl)carbonate; and

[0172] Their pesticide-acceptable salts.

[0173] In one embodiment, the nicotinamide compound may be, but is not limited to, N-(1-methyl-1H-tetrazol-5-yl)-2-(((2-methyl-2H-tetrazol-5-yl)methoxy)methyl)-6-(trifluoromethyl)nicotinamide.

[0174] The novel nicotinamide compounds described above or their pesticide-acceptable salts can be used as herbicidal active substances.

[0175]

[0176] The present inventors have developed a novel nicotinamide compound or an agrochemically acceptable salt thereof as described above, and the novel nicotinamide compound and the agrochemically acceptable salt thereof have excellent crop selectivity and herbicidal activity. The novel nicotinamide compound, its preparation method, and its herbicidal activity are described in detail in Korean Patent No. 10-2632628.

[0177] In addition, the present inventors confirmed that when the nicotinamide compound or its agrochemically acceptable salt described above is mixed with a phytosanitizer and used, phytosanitary damage is significantly reduced, thereby elucidating that crop protection and the range of applicable crops can be expanded. Therefore, the herbicidal composition comprising the nicotinamide compound or its agrochemically acceptable salt and the phytosanitizer of the present application described above can be a herbicidal composition with reduced phytosanitary damage compared to a herbicidal composition comprising only the nicotinamide compound or its agrochemically acceptable salt.

[0178] In this specification, the term "harm" may refer to damage to non-target plants as a side effect when treating with herbicidal substances. Spraying herbicides on plants can have various effects on the foliage (stems and leaves), roots, flowers, fruits, etc. Symptoms that appear on the foliage include leaf discoloration (yellowing phenomena such as chlorosis, chlorosis, deterioration, and chlorosis, or discoloration to brown, gray-white, yellow-brown, black-brown, etc. when a part of a living body such as a plant's organs, tissues, or cells dies), leaf deformities, and leaf fall. Symptoms that appear on the roots include root inhibition, deformed roots, browning, growth inhibition, root length, and root weight reduction. Symptoms that appear on flowers include delayed flowering, fallen fruit, weak spots, and blackening. Symptoms that appear on fruits include fruit drop, deformed fruits, weak spots, discoloration, and fertility problems.

[0179] As used herein, the term “weakening agent” means a chemical that reduces the negative effects of a herbicidal agent on non-target organisms, that is, beneficial crops, for example, a substance that protects crops from damage by the herbicidal agent but does not prevent the herbicidal agent from killing weeds.

[0180] In this specification, the term "plant" may be used interchangeably with "crop" and refers to all physical parts of a plant, including one or more parts selected from the group consisting of seeds, seedlings, seedlings, roots, tubers, stems, stalks, leaves and fruits.

[0181] In one embodiment, the laxative may be at least one laxative selected from the group consisting of isoxadifen-ethyl, benoxacor, dichlormid, and mefenpyr-diethyl, and may be, for example, isoxadifen-ethyl, but is not limited thereto.

[0182] In one embodiment, the weight ratio of the nicotinamide compound or its pesticide-acceptable salt and the laxative may be 1:0.05 to 1:20 (or 20:1 to 1:20), and more specifically, 1:0.05 to 1:20, 1:0.05 to 1:10, 1:0.05 to 1:5, 1:0.05 to 1:4, 1:0.05 to 1:3, 1:0.05 to 1:2.75, 1:0.05 to 1:2.5, 1:0.05 to 1:2, 1:0.05 to 1:1.9, 1:0.05 to 1:1.88, 1:0.05 to 1:1.875, 1:0.05 to 1:1, 1:0.1 to 1:20, 1:0.1 to 1:10, 1:0.1 to 1:5, 1:0.1 to 1:4, 1:0.1 to 1:3, 1:0.1 to 1:2.75, 1:0.1 to 1:2.5, 1:0.1 to 1:2, 1:0.1 to 1:1.9, 1:0.1 to 1:1.88, 1:0.1 to 1:1.875, 1:0.1 to 1:1, 1:0.2 to 1:20, 1:0.2 to 1:10, 1:0.2 to 1:5, 1:0.2 to 1:4, 1:0.2 to 1:3, 1:0.2 to 1:2.75, 1:0.2 to 1:2.5, 1:0.2 to 1:2, 1:0.2 to 1:1.9, 1:0.2 to 1:1.88, 1:0.2 to 1:1.875, 1:0.2 to 1:1, 1:0.25 to 1:20, 1:0.25 to 1:10, 1:0.25 to 1:5, 1:0.25 to 1:4, 1:0.25 to 1:3, 1:0.25 to 1:2.75, 1:0.25 to 1:2.5, 1:0.25 to 1:2, 1:0.25 to 1:1.9, 1:0.25 to 1:1.88, 1:0.25 to 1:1.875, 1:0.25 to 1:1, 1:0.333 to 1:20 (or 3:1 to 1:20), 1:0.333 to 1:10 (or 3:1 to 1:10), 1:0.333 to 1:5 (or 3:1 to 1:5), 1:0.333 to 1:4 (or 3:1 to 1:4), 1:0.333 to 1:3 (or 3:1 to 1:3), 1:0.333 to 1:2.75 (or 3:1 to 1:2.75), 1:0.333 to 1:2.5 (or 3:1 to 1:2.5), 1:0.333 to 1:2 (or 3:1 to 1:2), 1:0.333 to 1:1.9 (or 3:1 to 1:1.9), 1:0.333 to 1:1.88 (or 3:1 to 1:1.9), 1:0.333 to 1:1.875 (or 3:1 to 1:1.875), 1:0.333 to 1:1 (or 3:1 to 1:1), 1:0.5 to 1:20, 1:0.5 to 1:10, 1:0.5 to 1:5, 1:0.5 to 1:4, 1:0.5 to 1:3, 1:0.5 to 1:2.75, 1:0.5 to 1:2.5, 1:0.5 to 1:2, 1:0.5 to 1:1.9, 1:0.5 to 1:1.88, 1:0.5 to 1:1.875, 1:0.5 to 1:1, 1:1 to 1:20, 1:1 to 1:10, 1:1 to 1:5, 1:1 to 1:4, 1:1 to 1:3, 1:1 to 1:2.75, 1:1 to 1:2.5, 1:1 The weight ratio may be, but is not limited to, 1:2, 1:1 to 1:1.9, 1:1 to 1:1.88, or 1:1 to 1:1.875. The weight ratio may be, but is not limited to, the weight ratio of the final throughput.

[0183] In one embodiment, the treatment amount of the nicotinamide compound or its agrochemically feasible salt is 1 to 2000 g ai / ha, 1 to 1000 g ai / ha, 1 to 500 g ai / ha, 1 to 300 g ai / ha, 1 to 250 g ai / ha, 1 to 225 g ai / ha, 1 to 200 g ai / ha, 1 to 175 g ai / ha, 1 to 150 g ai / ha, 1 to 100 g ai / ha, 1 to 75 g ai / ha, 1 to 50 g ai / ha, 1 to 40 g ai / ha, 1 to 37.5 g ai / ha, 1 to 35 g ai / ha, 1 to 30 g ai / ha, 1 to 25 g ai / ha, 1 to 22.5 g ai / ha, 1 to 20 g ai / ha, 1 to 12.5 g ai / ha, 5 to 2000 g ai / ha, 5 to 1000 g ai / ha, 5 to 500 g ai / ha, 5 to 300 g ai / ha, 5 to 250 g ai / ha, 5 to 225 g ai / ha, 5 to 200 g ai / ha, 5 to 175 g ai / ha, 5 to 150 g ai / ha, 5 to 100 g ai / ha, 5 to 75 g ai / ha, 5 to 50 g ai / ha, 5 to 40 g ai / ha, 5 to 37.5 g ai / ha, 5 to 35 g ai / ha, 5 to 30 g ai / ha, 5 to 25 g ai / ha, 5 to 22.5 g ai / ha, 5 to 20 g ai / ha, 5 to 12.5 g ai / ha, 10 to 2000 g ai / ha, 10 to 1000 g ai / ha, 10 to 500 g ai / ha, 10 to 300 g ai / ha, 10 to 250 g ai / ha, 10 to 225 g ai / ha, 10 to 200 g ai / ha, 10 to 175 g ai / ha, 10 to 150 g ai / ha, 10 to 100 g ai / ha, 10 to 75 g ai / ha, 10 to 50 g ai / ha, 10 to 40 g ai / ha, 10 to 37.5 g ai / ha, 10 to 35 g ai / ha, 10 to 30 g ai / ha, 10 to 25 g ai / ha, 10 to 22.5 g ai / ha, 10 to 20 g ai / ha, 10 to 12.5 g ai / ha, 12.5 to 2000 g ai / ha, 12.5 to 1000 g ai / ha, 12.5 to 500 g ai / ha, 12.5 to 300 g ai / ha, 12.5 to 250 g ai / ha, 12.5 to 225 g ai / ha, 12.5 to 200 g ai / ha, 12.5 to 175 g ai / ha, 12.5 to 150 g ai / ha, 12.5 to 100 g ai / ha, 12.5 to 75 g ai / ha, 12.5 to 50 g ai / ha, 12.5 to 40 g ai / ha, 12.5 to 37.5 g ai / ha, 12.5 to 35 g ai / ha, 12.5 to 30 g ai / ha, 12.5 to 25 g ai / ha, 12.5 to 22.5 g ai / ha, 12.5 to 20 g ai / ha, 15 to 2000 g ai / ha, 15 to 1000 g ai / ha, 15 to 500 g ai / ha, 15 to 300 g ai / ha, 15 to 250 g ai / ha, 15 to 225 g ai / ha, 15 to 200 g ai / ha, 15 to 175 g ai / ha, 15 to 150 g ai / ha, 15 to 100 g ai / ha, 15 to 75 g ai / ha, 15 to 50 g ai / ha, 15 to 40 g ai / ha, 15 to 37.5 g ai / ha, 15 to 35 g ai / ha, 15 to 30 g ai / ha, 15 to 25 g ai / ha, 15 to 22.5 g ai / ha, 15 to 20 g ai / ha, 17.5 to 2000 g ai / ha, 17.5 to 1000 g ai / ha, 17.5 to 500 g ai / ha, 17.5 to 300 g ai / ha, 17.5 to 250 g ai / ha, 17.5 to 225 g ai / ha, 17.5 to 200 g ai / ha, 17.5 to 175 g ai / ha, 17.5 to 150 g ai / ha, 17.5 to 100 g ai / ha, 17.5 to 75 g ai / ha, 17.5 to 50 g ai / ha, 17.5 to 40 g ai / ha, 17.5 to 37.5 g ai / ha, 17.5 to 35 g ai / ha, 17.5 to 30 g ai / ha, 17.5 to 25 g ai / ha, 17.5 to 22.5 g ai / ha, 17.5 to 20 g ai / ha, 20 to 2000 g ai / ha, 20 to 1000 g ai / ha, 20 to 500 g ai / ha, 20 to 300 g ai / ha, 20 to 250 g ai / ha, 20 to 225 g ai / ha, 20 to 200 g ai / ha, 20 to 175 g ai / ha, 20 to 150 g ai / ha, 20 to 100 g ai / ha, 20 to 75 g ai / ha, 20 to 50 g ai / ha, 20 to 40 g ai / ha, 20 to 37.5 g ai / ha, 20 to 35 g ai / ha, 20 to 30 g ai / ha, 20 to 25 g ai / ha, 20 to 22.5 g ai / ha, 22.5 to 2000 g ai / ha, 22.5 to 1000 g ai / ha, 22.5 to 500 g ai / ha, 22.5 to 300 g ai / ha, 22.5 to 250 g ai / ha, 22.5 to 225 g ai / ha, 22.5 to 200 g ai / ha, 22.5 to 175 g ai / ha, 22.5 to 150 g ai / ha, 22.5 to 100 g ai / ha, 22.5 to 75 g ai / ha, 22.5 to 50 g ai / ha, 22.5 to 40 g ai / ha, 22.5 to 37.5 g ai / ha, 22.5 to 35 g ai / ha, 22.5 to 30 g ai / ha, 22.5 to 25 g ai / ha, 25 to 2000 g ai / ha, 25 to 1000 g ai / ha, 25 to 500 g ai / ha, 25 to 300 g ai / ha, 25 to 250 g ai / ha, 25 to 225 g ai / ha, 25 to 200 g ai / ha, 25 to 175 g ai / ha, 25 to 150 g ai / ha, 25 to 100 g ai / ha, 25 to 75 g ai / ha, 25 to 50 g ai / ha, 25 to 40 g ai / ha, 25 to 37.5 g ai / ha, 25 to 35 g ai / ha, or 25 to 30 g ai / ha, but is not limited thereto.

[0184] In one embodiment, the herbicidal composition may additionally include an agrochemically acceptable additive. The additive may be, but is not limited to, a carrier, surfactant, dispersant, adjuvant, or diluent commonly used in the formulation of agrochemicals.

[0185] In one embodiment, the herbicidal composition may be formulated as a wettable powder, suspension, emulsion, emulsifier, turbidity agent, liquid, dispersible liquid, granular wettable powder, granule, powder, liquid wettable powder, floating granule, or tablet, but is not limited thereto. These formulations may be used directly or may be diluted in an appropriate medium for processing.

[0186] The above surfactant is a substance with high surface activity, and may be an amphiphilic substance having hydrophilic and lipophilic molecular groups in the molecule. Such surfactants have excellent cleaning power, dispersing power, emulsifying power, solubilizing power, wetting power, sterilizing power, foaming power, and penetrating power, and thus, when included in a manufacturing composition, they have the function of wetting, disintegrating, dispersing, or emulsifying so as to effectively exhibit the medicinal effect. The above surfactant includes (C8∼C 12 alkyl)benzenesulfonate, (C3∼C6 alkyl)naphthalenesulfonate, di(C3∼C6 alkyl)naphthalenesulfonate, di(C8∼C 12 Alkyl)sulfosuccinate, lignin sulfonate, naphthalene sulfosuccinate formalin condensate, (C8∼C 12 Alkyl)naphthalene sulfonate formalin condensate, polyoxyethylene (C8∼C 12 Sodium or calcium salts of sulfonates such as alkyl)phenylsulfonate; (C8∼C 12 Alkyl) sulfate, polyoxyethylene (C8∼C 12 Alkyl) sulfate, polyoxyethylene (C8∼C 12 Anionic surfactants may be known, including sodium or calcium salts of sulfates such as alkyl)phenyl sulfate; sodium or calcium salts of succinates such as polyoxyalkylene succinate; etc. In addition, the surfactants include polyoxyethylene (C8∼C 12 Alkyl) ether, polyoxyethylene (C8∼C 12 Alkyl)phenyl ether, polyoxyethylene (C8∼C 12Nonionic surfactants such as alkyl)phenyl polymers may be included. The above surfactants may be used alone or in combination of two or more, and the surfactants that may be used in the present invention are not limited to the compounds exemplified above.

[0187] The above diluents can be classified into solid and liquid diluents based on their properties. Solid diluents with high absorbency are particularly suitable for making wettable powders. Liquid diluents and solvents should be stable and not undergo phase separation even at 0°C. Liquid diluents include water, toluene, xylene, petroleum ether, vegetable oil, acetone, methyl ethyl ketone, cyclohexanone, acid anhydrides, acetonitrile, acetophenone, amyl acetate, 2-butanone, butylene carbonate, chlorobenzene, cyclohexane, cyclohexanol, alkyl esters of acetic acid, 1,2-dichloropropane, diethanolamine, p-diethylbenzene, diethylene glycol, diethylene glycol abietate, diethylene glycol butyl ether, diethylene glycol ethyl ether, diethylene glycol methyl ether, N,N-dimethylformamide, dimethyl sulfoxide, 1,4-dioxane, dipropylene glycol, dipropylene glycol methyl ether, dipropylene glycol dibenzoate, diproxytol, Alkylpyrrolidone, ethyl acetate, 2-ethyl hexanol, ethylene carbonate, 1,1,1-trichloroethane, 2-heptanone, alpha-pinene, d-limonene, ethyl lactate, ethylene glycol, ethylene glycol butyl ether, ethylene glycol methyl ether, gamma-butyrolactone, glycerol, glycerol acetate, glycerol diacetate, glycerol triacetate, hexadecane, hexylene glycol, isoamyl acetate, isobornyl acetate, isooctane, isophorone, isopropylbenzene, isopropyl myristate, lactic acid, laurylamine, mesityl oxide, methoxypropanol, methyl isoamyl ketone, methyl isobutyl ketone, methyl laurate, methyl octanoate, methyl Oleate, methylene chloride, m-xylene, n-hexane, n-octylamine, octadecanoic acid, octylamine acetate, oleic acid, oleylamine, o-xylene, phenol, polyethylene glycol (PEG 400), propionic acid, propyl lactate, propylene carbonate, propylene glycol, propylene glycol methyl ether, p-xylene, toluene,Triethyl phosphate, triethylene glycol, xylenesulfonic acid, paraffin, mineral oil, trichloroethylene, perchloroethylene, ethyl acetate, amyl acetate, butyl acetate, propylene glycol methyl ether, diethylene glycol methyl ether, methanol, ethanol, isopropanol, and high molecular weight alcohols such as amyl alcohol, tetrahydrofurfuryl alcohol, hexanol, octanol, ethylene glycol, propylene glycol, glycerol, N-methyl-2-pyrrolidone, etc. can be used. Solid diluents such as talc, titanium dioxide, pyrophyllite clay, silica, attapulgite clay, diatomaceous earth, limestone, calcium carbonate, bentonite, calcium montmorillonite, cottonseed hulls, wheatmeal, soybean meal, pumice stone, wood flour, walnut shells, lignin, etc. can be used.

[0188] In addition, when formulating the herbicidal composition of the present application, a small amount of other additives may be added to prevent foaming, caking, corrosion, microbial growth, etc.

[0189] The herbicidal composition of the present application is prepared using conventional methods. For liquid formulations, simply mix the components, while fine solid compositions can be prepared by mixing and grinding in a hammer or fluidized bed mill. For suspensions, the composition can be prepared by mixing in a wet mill, and granular formulations can be prepared by spraying the active ingredient onto a granular carrier.

[0190] In one embodiment, the herbicidal composition comprises an acetyl-CoA carboxylase (ACCase) inhibitor, an acetolactate synthase (ALS) inhibitor, a microtubule polymerization inhibitor, an auxin mimetic herbicide, a photosynthesis (photosystem II) inhibitor, an EPSP synthase (5-enolpyruvylshikimate-3-phosphate synthase) inhibitor, a glutamine synthetase inhibitor, a PDS (phytoene desaturase) inhibitor, a DOXP (1-deoxy-D-xylulose 5-phosphate) synthase inhibitor, a PPO (protoporphyrinogen oxidase) inhibitor, a VLCFAs (very long chain fatty acid) synthesis inhibitor, DHP (dihydropteroate) inhibitor, auxin transport inhibitor, photosystem I electron conversion agent, microtubule formation inhibitor, uncoupling (membrane disrupting) agent, HPPD (hydroxyphenylpyruvate dioxygenase) inhibitor, cellulose synthesis inhibitor, fatty acid thioesterase inhibitor, serine-threonine protein phosphatase inhibitor, solanesyl diphosphate synthase inhibitor,It may or may not additionally contain one or more herbicidal active substances selected from the group consisting of homogentisate solanesyltransferase inhibitors, lycopene cyclase inhibitors and other herbicides.

[0191] Examples of the above acetyl-CoA carboxylase inhibitors include cyclohexanedione series clethodim, cyclooxydim, propoxydim, sethoxydim, tepraloxydim, and tralkoxydim; aryloxyphenoxy-propionate series clodinafop-propargyl, cyhalofop-butyl, diclofop-methyl, phenoxaprop-ethyl, phenoxaprop-P-ethyl, fenthiaprop, fluazifop-butyl, fluazifop-P-butyl, haloxyfop-methyl, haloxyfop-ethoxyethyl, haloxyfop-P-methyl, metamifop, quizalofop-ethyl, quizalofop-P-ethyl, and quizalofop-tefuryl; and pinoxadene, which does not belong to a specific chemical series.

[0192] The above acetolactate synthase inhibitors include imidazolinone series imazametabenz-methyl, imazamox, imazapic, imazapyr, imazaquin, imazethapyr, etc.; pyrimidinyl benzoate series bispyribac-sodium, pyribenzoxime, pyriptalide, pyriminobac-methyl, pyrithiobac-sodium, etc.; sulfonylurea series amidosulfuron, azimsulfuron, bensulfuron-methyl, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cyclosulfamuron, ethametsulfuron-methyl, ethoxysulfuron, plazasulfuron, flucetosulfuron, flupyrsulfuron-methyl-sodium, foramsulfuron, halosulfuron-methyl, imazosulfuron, iodosulfuron-methyl-sodium; Mezosulfuron-methyl, metazosulfuron, metsulfuron-methyl, nicosulfuron, olsosulfamuron, pyrimisulfuron-methyl, propyrisulfuron, prosulfuron, pyrazosulfuron-ethyl, rimsulfuron, sulfometuron-methyl, sulfosulfuron, triasulfuron, tribenuron-methyl, thifensulfuron-methyl, trifloxysulfuron-sodium, triflusulfuron-methyl, tritosulfuron, etc.; sulfonanilide series pyrimisulfan, triapamon, etc.; triazolid series flucarbazone-sodium, propoxycarbazone-sodium, thienecarbazone-methyl, etc.; triazolopyrimidine series chloransulam-methyl, diclosulam, florasulam, flumetsulam, metosulam, penoxsulam, piroxsulam, etc.

[0193] As the above microtubule assembly inhibitor, dinitroaniline series benepin (benfluralin), butralin, ethalfluralin, oryzalin, prodiamine, pendimethalin, trifluralin, etc., phosphoramidate series butamiphos, DMPA, etc., pyridine series dithiopyr, thiazopyr, etc., and non-specific chemical series chlorthaldi-methyl, propyzamide (pronamide), etc. can be used.

[0194] Examples of the above auxin-mimetic herbicides include chloramben, dicamba, etc. from the benzoate series; 2,4,5-T, 2,4-D, 2,4-DB, clomeprop, dichlorprop, MCPA, MCBP, mecoprop, etc. from the phenoxy-carboxylate series; aminopyralid, clopyralid, florpyroxifene (florpyroxifene-benzyl), haloxyphene, picloram, etc. from the pyridine-carboxylate series; fluraxypyr, triclopyr, etc. from the pyridyloxy-carboxylate series; cyclolac, quinmerac, etc. from the quinoline-carboxylate series; and aminocyclopyrachlor, benazoline-ethyl, etc. that do not belong to a specific chemical series.

[0195] The photosynthetic photosystem II inhibitors include chloranocryl (dacryl), propanil, etc. of the amide series, desmedipham, phenmedipham, etc. of the phenylcarbamate series, ametrin, atrazine, cyanazine, dimethamethrin, prometon, promethrin, propazine, simazine, terbuthylazine, terbudrin, etc. of the triazine series, hexazinone, metamitrone, metribuzin, etc. of the triazinone series, bromacil, lenacil, terbacil, etc. of the uracil series, chlorotoluron, diuron, fluometuron, isoproturon, linuron, metobromuron, metabenzthiazuron, monuron, terbuthiuron, etc. of the urea series, bromoxynil, ioxynil, etc. of the nitrile series, amicarbazone, chloridazone (pyrazon), bentazone, pyridate, etc. that do not belong to a specific chemical series. It can be used.

[0196] Glyphosate, etc. can be used as the above EPSP synthase inhibitor.

[0197] As the above glutamine synthase inhibitor, phosphonic acid series vilanaphos (bialaphos) and glufosinate-ammonium can be used.

[0198] As the above PDS inhibitors, diphenyl heterocycle series fluridone, flutamone, etc., en-phenyl heterocycle series flurochloridone, noflurazon, etc., phenyl ether series beflubutamide, diflufenican, picolinafen, etc. can be used.

[0199] As the above DOXP synthase inhibitor, isoxazolidinone series drugs such as bixlozone and clomazone can be used.

[0200] Examples of the above PPO inhibitors include diphenyl ether series such as acifluorfen, bifenox, fomesafen, lactofen, and oxyfluorfen; N-phenyl-imide series such as butafenacil, cinidon-ethyl, flumiclorac-pentyl, flumioxazin, fluthiacet-methyl, pentoxazone, saflufenacil, tiafenacil, and trifludimoxazin; N-phenyl-oxadiazolone series such as oxadiazolyl and oxadiazolone; N-phenyl-triazolinone series such as azafenidine, carfentrazone-ethyl, and sulfentrazone; and non-specific chemical series such as pyraflufen-ethyl and pyraclonil.

[0201] The above VLCFAs synthesis inhibitors include acetochlor, alachlor, butachlor, dimethachlor, dimethenamide, metazachlor, metolachlor, petoxamide, pretilachlor, propachlor, tenichlor, propisochlor, etc. from the alpha-chloroacetamide series, anilophos, piperophos, etc. from the alpha-thioacetamide series, mefenacet, flufenacet, etc. from the alpha-oxyacetamide series, capenstrol, pentrazamide, ifencarbazone, etc. from the azolyl-carboxamide series, benfurasate, etofumesate, etc. from the benzofuran series, phenoxasulfone, pyroxasulfone, etc. from the isoxazoline series, indanophane, tridipane, etc. from the oxirane series, cycloate, dimepiperate, EPTC, from the thiocarbamate series. Esprocarb, molinate, orbencarb, prosulfocarb, tiobencarb (bentiocarb), tri-allate, and vernolate can be used.

[0202] As the above DHP inhibitor, Asullam, etc. can be used.

[0203] As the above auxin transport inhibitor, diflufenzopyr and napthalam of the aryl-carboxylate series can be used.

[0204] As the photosystem I electron conversion herbicide, pyridinium series herbicides such as diquat and paraquat can be used.

[0205] As the above microtubule tissue inhibitor, carbamate series agents such as barban, carbetamide, and chlorpropham can be used.

[0206] As the above uncoupler herbicide, dinitrophenol series products such as Dinocep and DNOC can be used.

[0207] As the above HPPD inhibitor, pyrazole series benzophenap, pyrasulfotole, pyrazolinate, pyrazoxyfen, tolpyralate, topramezone, etc., triaketone series benzobicyclone, bicyclopyrone, fenquinotrione, mesotrione, sulcotrione, tembotrione, tefuryltrione, etc., and isoxaflutole, which does not belong to a specific chemical series, can be used.

[0208] As the above cellulose synthesis inhibitor, indaziflam and triaziflam of the alkylazine series, chlorthiamide and dichlovenil of the nitrile series, and flupoxam and isoxaben of non-specific chemical series can be used.

[0209] As the above fatty acid thioesterase inhibitor, benzyl ether series compounds such as cinmethylin and methiozolin can be used.

[0210] Endothel, etc. can be used as the above serine threonine protein kinase inhibitor.

[0211] Aclonifene, etc. can be used as the above solanesyl diphosphite synthase inhibitor.

[0212] Cyclopyrimorate, etc. can be used as the above homogentisate solanesyltransferase inhibitor.

[0213] Amitrol, etc. can be used as the above lycopene cyclase inhibitor.

[0214] Other herbicides that can be used include bensulide, bromobutide, cumyluron, difenzoquat, pyributicarb, DSMA, MSMA, dimron (daimuron), etobenzanid, flamprop-M, phosamine, oxaziclomefone, pelargonic acid, diphenamide, maproanilide, napropamide, etc.

[0215] In one embodiment, the herbicidal composition provided herein can be used to control weeds during crop cultivation. There is no particular limitation on the crops to which the composition provided herein can be applied, and any of the crops can be selected from prokaryotic plants (e.g., algae, etc.) and eukaryotic plants. In one example, the crop may be at least one selected from the group consisting of, but is not limited to, a plant of the Gramineae family, a corn plant (e.g., corn (Zea mays)), a plant of the Gramineae family, a plant of the Sorghum family, a plant of the Sorghum family, a plant of the Cotton plant (e.g., cotton plant; Gossypium), a plant of the Solanaceae family, a plant of the Solanaceae family, a plant of the Solanaceae family, a plant of the Coffea family, a plant of the Coffea family, a plant of the Coffea arabica family, a plant of the Liliaceae family, a plant of the Allium family, a plant of the Allium family, a plant of the Garlic family, a plant of the Grape ...

[0216] In one embodiment, the herbicidal composition may be one in which the damage to crops caused by the nicotinamide compound represented by the chemical formula 1 or an agrochemically acceptable salt thereof is reduced. For example, the crop may be corn. The present inventors have confirmed that the nicotinamide compound or an agrochemically acceptable salt thereof can be usefully utilized for weed control during corn cultivation, and in particular, when a herbicidal composition comprising the nicotinamide compound or an agrochemically acceptable salt thereof and a harm reducer is used, the damage to corn is significantly reduced.

[0217] In one embodiment, the crop may be corn, such as, but not limited to, popcorn (e.g., K-pop, etc.), field corn (e.g., Gwangmyeongok, etc.), or sweet corn (e.g., Heukjinjuchal, Heukmichal, Chodang, etc.).

[0218] In this specification, the term “weed” refers to an unwanted plant that grows in a crop field and requires control. In a conventional weed classification method, weeds are classified into grass weeds, cypress weeds, and broadleaf weeds according to their shape. The grass weeds include sorghum, rye, wheatgrass, American dandelion, barley, common barley, king barley, dogtail, sedge, autumn dogtail, deureungsae, binori, large binori, garakjijo, poa grass, or king poa grass, etc. The cypress weeds include golden dongsani, tadpole gorangi, hyangbuja, neodobangdongsani, soetolgol, olbangae, and maejagi, etc. The broadleaf weeds include water parsley, black nightshade, cocklebur, dandelion, dwarf dandelion, dwarf dandelion, bindweed, and kudzu, etc.

[0219] Also, depending on the number of leaves, weeds are classified as monocotyledonous or dicotyledonous weeds. Monocotyledonous weed species may include grasses such as barnacles, wheatgrass, pi, American dandelion, common barnacles, king barnacles, dogtail grass, Korean dogtail grass, autumn dogtail grass, deureungsae, binori, large binori, garakjijo, poa grass or king poa grass. Dicotyledonous weed species include Asteraceae weeds such as yeoncho, hairy jindeukchal, middle head grass, crown daisy, mugwort, American cicada, western dandelion, common forget-me-not, forget-me-not, hairy starflower, jijigae, barley weed, mugwort, wild wormwood, goblin needle, jindeukchal, maple leaf ragweed, sseumbaegi, godulppaegi, king godulppaegi, American aster, jobangi, dandelion, ragweed, aster, red sesame, etc. Weeds of the Lamiaceae family, such as honeysuckle, dandelion, perilla, and motherwort; weeds of the Euphorbiaceae family, such as sesame, large ground beetle, and baby ground beetle; weeds of the Scrophulariaceae family, such as wrinkled leaf and field ridge grass; weeds of the Solanaceae family, such as black nightshade and American black nightshade; weeds of the Amaranthaceae family, such as common amaranth, fine hairy amaranth, and kochia; weeds of the Oxalis family, such as sorrel and oxalis; weeds of the Clematis family, such as European mousegrass, and schisandra; weeds of the Malvaceae family, such as watermelon plant and ablution; weeds of the Hemlock family, such as ginseng and hemp; weeds of the Arrhenius family, such as perilla and double evening primrose; weeds of the Purslane family, such as purslane; weeds of the Equisetum family, such as horsetail; weeds of the Araceae family, such as pinellia; weeds of the Umbelliferae family, such as sasaeng; weeds of the Pomegranate family, such as pomegranate; weeds of the Commelinaceae family, such as Commelinae; This may include weeds from the Crassulaceae family, such as Sedum; weeds from the Papaveraceae family, such as Celandine; weeds from the Gallicaceae family, such as Milk thistle; weeds from the Violaceae family, such as Violaceae; weeds from the Caryophyllaceae family, such as Starflower; weeds from the Nettle family, such as Moshimultongi; weeds from the Boraginaceae family, such as Kkotmari; weeds from the Plantagoceae family, such as Plantain; weeds from the Rosaceae family, such as Gaesosirangaebi; and weeds from the Water Hyacinth family, such as Water Hyacinth.

[0220] In one embodiment, the herbicidal composition may control at least one selected from the group consisting of grass weeds, cycad weeds, and broadleaf weeds, but is not limited thereto. The grass weeds may be sorghum, common dandelion, wheatgrass, American dandelion, or barnyard grass, the cycad weed may be dandelion, and the broadleaf weeds may be dandelion, cocklebur, common dandelion, common dandelion, dandelion, or kudzu, but is not limited thereto.

[0221] According to another aspect of the present application, the present application provides a composition comprising the nicotinamide compound or an agrochemically acceptable salt thereof and the phytoprotector, for use as a herbicide and / or for controlling weeds. The composition may be a herbicidal composition having significantly reduced phytoprotective effects compared to a herbicidal composition comprising only the nicotinamide compound or an agrochemically acceptable salt thereof.

[0222] In the use of the composition comprising the nicotinamide compound or an agrochemically acceptable salt thereof and the pesticide of the present application as a herbicide and / or for controlling weeds, the details of the nicotinamide compound or an agrochemically acceptable salt thereof and the pesticide, the pest, the plant, the weight ratio, etc. are as described in the herbicidal composition, which is one embodiment of the present application.

[0223] According to another aspect of the present application, the present application provides a use for the preparation of a herbicidal composition comprising the nicotinamide compound or an agrochemically acceptable salt thereof and a phytosanitizer. The herbicidal composition may be a herbicidal composition having significantly reduced phytosanitary effects compared to a herbicidal composition comprising only the nicotinamide compound or an agrochemically acceptable salt thereof.

[0224] In the use for manufacturing a herbicidal composition of the nicotinamide compound or an agrochemically acceptable salt thereof and a phytosanitizer of the present application, the details of the nicotinamide compound or an agrochemically acceptable salt thereof and the phytosanitizer, the phytosanitizer, the plant, the weight ratio, etc. are as described in the herbicidal composition of one embodiment of the present application described above.

[0225] According to another aspect of the present application, the present application provides a method for preparing a herbicidal composition, comprising a step of mixing the nicotinamide compound or an agrochemically acceptable salt thereof and a laxative.

[0226] The above herbicidal composition may be a herbicidal composition having significantly reduced toxicity compared to a herbicidal composition containing only the nicotinamide compound or an agrochemically acceptable salt thereof.

[0227] The nicotinamide compound or its pesticide-acceptable salt and the laxative can be mixed in a weight ratio of 1:0.05 to 1:20 (or 20:1 to 1:20), more specifically, 1:0.05 to 1:20, 1:0.05 to 1:10, 1:0.05 to 1:5, 1:0.05 to 1:4, 1:0.05 to 1:3, 1:0.05 to 1:2.75, 1:0.05 to 1:2.5, 1:0.05 to 1:2, 1:0.05 to 1:1.9, 1:0.05 to 1:1.88, 1:0.05 to 1:1.875, 1:0.05 to 1:1, 1:0.1 to 1:20, 1:0.1 to 1:10, 1:0.1 to 1:5, 1:0.1 to 1:4, 1:0.1 to 1:3, 1:0.1 to 1:2.75, 1:0.1 to 1:2.5, 1:0.1 to 1:2, 1:0.1 to 1:1.9, 1:0.1 to 1:1.88, 1:0.1 to 1:1.875, 1:0.1 to 1:1, 1:0.2 to 1:20, 1:0.2 to 1:10, 1:0.2 to 1:5, 1:0.2 to 1:4, 1:0.2 to 1:3, 1:0.2 to 1:2.75, 1:0.2 to 1:2.5, 1:0.2 to 1:2, 1:0.2 to 1:1.9, 1:0.2 to 1:1.88, 1:0.2 to 1:1.875, 1:0.2 to 1:1, 1:0.25 to 1:20, 1:0.25 to 1:10, 1:0.25 to 1:5, 1:0.25 to 1:4, 1:0.25 to 1:3, 1:0.25 to 1:2.75, 1:0.25 to 1:2.5, 1:0.25 to 1:2, 1:0.25 to 1:1.9, 1:0.25 to 1:1.88, 1:0.25 to 1:1.875, 1:0.25 to 1:1, 1:0.333 to 1:20 (or 3:1 to 1:20), 1:0.333 to 1:10 (or 3:1 to 1:10), 1:0.333 to 1:5 (or 3:1 to 1:5), 1:0.333 to 1:4 (or 3:1 to 1:4), 1:0.333 to 1:3 (or 3:1 to 1:3), 1:0.333 to 1:2.75 (or 3:1 to 1:2.75), 1:0.333 to 1:2.5 (or 3:1 to 1:2.5), 1:0.333 to 1:2 (or 3:1 to 1:2), 1:0.333 to 1:1.9 (or 3:1 to 1:1.9), 1:0.333 to 1:1.88 (or 3:1 to 1:1.9), 1:0.333 to 1:1.875 (or 3:1 to 1:1.875), 1:0.333 to 1:1 (or 3:1 to 1:1), 1:0.5 to 1:20, 1:0.5 to 1:10, 1:0.5 to 1:5, 1:0.5 to 1:4, 1:0.5 to 1:3, 1:0.5 to 1:2.75, 1:0.5 to 1:2.5, 1:0.5 to 1:2, 1:0.5 to 1:1.9, 1:0.5 to 1:1.88, 1:0.5 to 1:1.875, 1:0.5 to 1:1, 1:1 to 1:20, 1:1 to 1:10, 1:1 to 1:5, 1:1 to 1:4, 1:1 to 1:3, 1:1 to 1:2.75, 1:1 to 1:2.5, 1:1 The weight ratio may be, but is not limited to, 1:2, 1:1 to 1:1.9, 1:1 to 1:1.88, or 1:1 to 1:1.875. The weight ratio may be, but is not limited to, the weight ratio of the final processing amount.

[0228] In the method for manufacturing the herbicidal composition of the present application, the contents of the nicotinamide compound or its pesticide-acceptable salt and the phytoprotector, phytoprotector, plant, weight ratio, additives, etc. are as described in the herbicidal composition of one embodiment of the present application described above.

[0229]

[0230] According to another aspect of the present application, the present application provides a method for controlling weeds in a cultivation field, comprising the step of applying an effective amount of the herbicidal composition described above to the cultivation field.

[0231] In one embodiment, the herbicidal composition can be applied after weed emergence; before emergence; or both after emergence and before emergence to control weeds.

[0232] In one embodiment, the herbicidal composition can be applied to a field before germination of a crop; after germination; or both before and after germination.

[0233] In one embodiment, the treatment of the herbicidal composition is performed by directly spraying an effective amount for weed control onto the stem and leaf portion of the weed as is, or in a form of an appropriate dilution or suspension with water, etc., to control various weeds, and may also be used by treating the seeds of useful plants such as soaking seeds in the herbicide, seed dressing, and kalpa treatment, mixing the entire layer of the soil, applying seed furrow, mixing in topsoil, treating cell seedlings, treating planting holes, applying a base, top dressing, and applying the surface of the water, etc., by treating the soil or a cultivation carrier. In addition, the treatment may be carried out in the form of a ready-to-spray aqueous solution, powder, suspension, high-concentration aqueous solution, oily or other suspension or dispersion, emulsion, oil dispersion, paste, dust, material for broadcasting or granulation, using a method such as spraying, atomizing, dusting, broadcasting or watering as the treatment form. The treatment form may vary depending on the purpose.

[0234] As used herein, the term "effective amount" refers to an amount of a pesticide active ingredient or composition sufficient to achieve a biological effect, such as control of harmful weeds or protection of a crop, without causing substantial damage to the treated plants. This amount can vary widely and depends on various factors, such as the species of weed to be controlled, the crop or material being treated, climatic conditions, and the specific pesticide active ingredient used.

[0235] In one embodiment, the herbicidal composition of the present invention comprises at least 0.5 wt% to 50 wt%, 0.5 wt% to 40 wt%, 0.5 wt% to 30 wt%, 0.5 wt% to 20 wt%, 0.5 wt% to 10 wt%, 0.5 wt% to 7.5 wt%, 0.5 wt% to 5 wt%, 0.5 wt% to 4.5 wt%, 0.5 wt% to 4 wt%, 1 wt% to 50 wt%, 1 wt% to 40 wt%, 1 wt% to 30 wt%, 1 wt% to 20 wt%, 1 wt% to 10 wt%, 1 wt% to 7.5 wt%, 1 wt% to 5 wt%, 1 wt% to 4.5 wt% % by weight, 1 wt% to 4 wt%, 2 wt% to 50 wt%, 2 wt% to 40 wt%, 2 wt% to 30 wt%, 2 wt% to 20 wt%, 2 wt% to 10 wt%, 2 wt% to 7.5 wt%, 2 wt% to 5 wt%, 2 wt% to 4.5 wt%, 2 wt% to 4 wt%, 3 wt% to 50 wt%, 3 wt% to 40 wt%, 3 wt% to 30 wt%, 3 wt% to 20 wt%, 3 wt% to 10 wt%, 3 wt% to 7.5 wt%, 3 wt% to 5 wt%, 3 wt% to 4.5 wt%, 3 wt% to 4 wt%, 4 wt% to 50 wt%, 4 wt% to 40 wt%, 4 wt% to 30 wt%, 4 It may include, but is not limited to, from 4 wt% to 20 wt%, from 4 wt% to 10 wt%, from 4 wt% to 7.5 wt%, from 4 wt% to 5 wt%, or from 4 wt% to 4.5 wt%.

[0236] In one embodiment, the treatment amount of the nicotinamide compound or its agrochemically feasible salt is 1 to 2000 g ai / ha, 1 to 1000 g ai / ha, 1 to 500 g ai / ha, 1 to 300 g ai / ha, 1 to 250 g ai / ha, 1 to 225 g ai / ha, 1 to 200 g ai / ha, 1 to 175 g ai / ha, 1 to 150 g ai / ha, 1 to 100 g ai / ha, 1 to 75 g ai / ha, 1 to 50 g ai / ha, 1 to 40 g ai / ha, 1 to 37.5 g ai / ha, 1 to 35 g ai / ha, 1 to 30 g ai / ha, 1 to 25 g ai / ha, 1 to 22.5 g ai / ha, 1 to 20 g ai / ha, 1 to 12.5 g ai / ha, 5 to 2000 g ai / ha, 5 to 1000 g ai / ha, 5 to 500 g ai / ha, 5 to 300 g ai / ha, 5 to 250 g ai / ha, 5 to 225 g ai / ha, 5 to 200 g ai / ha, 5 to 175 g ai / ha, 5 to 150 g ai / ha, 5 to 100 g ai / ha, 5 to 75 g ai / ha, 5 to 50 g ai / ha, 5 to 40 g ai / ha, 5 to 37.5 g ai / ha, 5 to 35 g ai / ha, 5 to 30 g ai / ha, 5 to 25 g ai / ha, 5 to 22.5 g ai / ha, 5 to 20 g ai / ha, 5 to 12.5 g ai / ha, 10 to 2000 g ai / ha, 10 to 1000 g ai / ha, 10 to 500 g ai / ha, 10 to 300 g ai / ha, 10 to 250 g ai / ha, 10 to 225 g ai / ha, 10 to 200 g ai / ha, 10 to 175 g ai / ha, 10 to 150 g ai / ha, 10 to 100 g ai / ha, 10 to 75 g ai / ha, 10 to 50 g ai / ha, 10 to 40 g ai / ha, 10 to 37.5 g ai / ha, 10 to 35 g ai / ha, 10 to 30 g ai / ha, 10 to 25 g ai / ha, 10 to 22.5 g ai / ha, 10 to 20 g ai / ha, 10 to 12.5 g ai / ha, 12.5 to 2000 g ai / ha, 12.5 to 1000 g ai / ha, 12.5 to 500 g ai / ha, 12.5 to 300 g ai / ha, 12.5 to 250 g ai / ha, 12.5 to 225 g ai / ha, 12.5 to 200 g ai / ha, 12.5 to 175 g ai / ha, 12.5 to 150 g ai / ha, 12.5 to 100 g ai / ha, 12.5 to 75 g ai / ha, 12.5 to 50 g ai / ha, 12.5 to 40 g ai / ha, 12.5 to 37.5 g ai / ha, 12.5 to 35 g ai / ha, 12.5 to 30 g ai / ha, 12.5 to 25 g ai / ha, 12.5 to 22.5 g ai / ha, 12.5 to 20 g ai / ha, 15 to 2000 g ai / ha, 15 to 1000 g ai / ha, 15 to 500 g ai / ha, 15 to 300 g ai / ha, 15 to 250 g ai / ha, 15 to 225 g ai / ha, 15 to 200 g ai / ha, 15 to 175 g ai / ha, 15 to 150 g ai / ha, 15 to 100 g ai / ha, 15 to 75 g ai / ha, 15 to 50 g ai / ha, 15 to 40 g ai / ha, 15 to 37.5 g ai / ha, 15 to 35 g ai / ha, 15 to 30 g ai / ha, 15 to 25 g ai / ha, 15 to 22.5 g ai / ha, 15 to 20 g ai / ha, 17.5 to 2000 g ai / ha, 17.5 to 1000 g ai / ha, 17.5 to 500 g ai / ha, 17.5 to 300 g ai / ha, 17.5 to 250 g ai / ha, 17.5 to 225 g ai / ha, 17.5 to 200 g ai / ha, 17.5 to 175 g ai / ha, 17.5 to 150 g ai / ha, 17.5 to 100 g ai / ha, 17.5 to 75 g ai / ha, 17.5 to 50 g ai / ha, 17.5 to 40 g ai / ha, 17.5 to 37.5 g ai / ha, 17.5 to 35 g ai / ha, 17.5 to 30 g ai / ha, 17.5 to 25 g ai / ha, 17.5 to 22.5 g ai / ha, 17.5 to 20 g ai / ha, 20 to 2000 g ai / ha, 20 to 1000 g ai / ha, 20 to 500 g ai / ha, 20 to 300 g ai / ha, 20 to 250 g ai / ha, 20 to 225 g ai / ha, 20 to 200 g ai / ha, 20 to 175 g ai / ha, 20 to 150 g ai / ha, 20 to 100 g ai / ha, 20 to 75 g ai / ha, 20 to 50 g ai / ha, 20 to 40 g ai / ha, 20 to 37.5 g ai / ha, 20 to 35 g ai / ha, 20 to 30 g ai / ha, 20 to 25 g ai / ha, 20 to 22.5 g ai / ha, 22.5 to 2000 g ai / ha, 22.5 to 1000 g ai / ha, 22.5 to 500 g ai / ha, 22.5 to 300 g ai / ha, 22.5 to 250 g ai / ha, 22.5 to 225 g ai / ha, 22.5 to 200 g ai / ha, 22.5 to 175 g ai / ha, 22.5 to 150 g ai / ha, 22.5 to 100 g ai / ha, 22.5 to 75 g ai / ha, 22.5 to 50 g ai / ha, 22.5 to 40 g ai / ha, 22.5 to 37.5 g ai / ha, 22.5 to 35 g ai / ha, 22.5 to 30 g ai / ha, 22.5 to 25 g ai / ha, 25 to 2000 g ai / ha, 25 to 1000 g ai / ha, 25 to 500 g ai / ha, 25 to 300 g ai / ha, 25 to 250 g ai / ha, 25 to 225 g ai / ha, 25 to 200 g ai / ha, 25 to 175 g ai / ha, 25 to 150 g ai / ha, 25 to 100 g ai / ha, 25 to 75 g ai / ha, 25 to 50 g ai / ha, 25 to 40 g ai / ha, 25 to 37.5 g ai / ha, 25 to 35 g ai / ha, or 25 to 30 g ai / ha, but is not limited thereto.

[0237] The effective amount of the herbicide included in the above herbicidal composition can be mixed with a nicotinamide compound or an agrochemically acceptable salt thereof in the weight ratio described above. More specifically, the nicotinamide compound or its pesticide-acceptable salt and the laxative can be mixed in a weight ratio of 1:0.05 to 1:20 (or 20:1 to 1:20), and more specifically, 1:0.05 to 1:20, 1:0.05 to 1:10, 1:0.05 to 1:5, 1:0.05 to 1:4, 1:0.05 to 1:3, 1:0.05 to 1:2.75, 1:0.05 to 1:2.5, 1:0.05 to 1:2, 1:0.05 to 1:1.9, 1:0.05 to 1:1.88, 1:0.05 to 1:1.875, 1:0.05 to 1:1, 1:0.1 to 1:20, 1:0.1 to 1:10, 1:0.1 to 1:5, 1:0.1 to 1:4, 1:0.1 to 1:3, 1:0.1 to 1:2.75, 1:0.1 to 1:2.5, 1:0.1 to 1:2, 1:0.1 to 1:1.9, 1:0.1 to 1:1.88, 1:0.1 to 1:1.875, 1:0.1 to 1:1, 1:0.2 to 1:20, 1:0.2 to 1:10, 1:0.2 to 1:5, 1:0.2 to 1:4, 1:0.2 to 1:3, 1:0.2 to 1:2.75, 1:0.2 to 1:2.5, 1:0.2 to 1:2, 1:0.2 to 1:1.9, 1:0.2 to 1:1.88, 1:0.2 to 1:1.875, 1:0.2 to 1:1, 1:0.25 to 1:20, 1:0.25 to 1:10, 1:0.25 to 1:5, 1:0.25 to 1:4, 1:0.25 to 1:3, 1:0.25 to 1:2.75, 1:0.25 to 1:2.5, 1:0.25 to 1:2, 1:0.25 to 1:1.9, 1:0.25 to 1:1.88, 1:0.25 to 1:1.875, 1:0.25 to 1:1, 1:0.333 to 1:20 (or 3:1 to 1:20), 1:0.333 to 1:10 (or 3:1 to 1:10), 1:0.333 to 1:5 (or 3:1 to 1:5), 1:0.333 to 1:4 (or 3:1 to 1:4), 1:0.333 to 1:3 (or 3:1 to 1:3), 1:0.333 to 1:2.75 (or 3:1 to 1:2.75), 1:0.333 to 1:2.5 (or 3:1 to 1:2.5), 1:0.333 to 1:2 (or 3:1 to 1:2), 1:0.333 to 1:1.9 (or 3:1 to 1:1.9), 1:0.333 to 1:1.88 (or 3:1 to 1:1.9), 1:0.333 to 1:1.875 (or 3:1 to 1:1.875), 1:0.333 to 1:1 (or 3:1 to 1:1), 1:0.5 to 1:20, 1:0.5 to 1:10, 1:0.5 to 1:5, 1:0.5 to 1:4, 1:0.5 to 1:3, 1:0.5 to 1:2.75, 1:0.5 to 1:2.5, 1:0.5 to 1:2, 1:0.5 to 1:1.9, 1:0.5 to 1:1.88, 1:0.5 to 1:1.875, 1:0.5 to 1:1, 1:1 to 1:20, 1:1 to 1:10, 1:1 to It can be mixed in a weight ratio of, but not limited to, 1:5, 1:1 to 1:4, 1:1 to 1:3, 1:1 to 1:2.75, 1:1 to 1:2.5, 1:1 to 1:2, 1:1 to 1:1.9, 1:1 to 1:1.88, or 1:1 to 1:1.875. The weight ratio may be, but is not limited to, the weight ratio of the final processing amount.

[0238] In the method for controlling weeds in the cultivation field of the present application, the contents of the nicotinamide compound or its agrochemically acceptable salt and the phytoprotector, phytoprotector, plant, weight ratio, etc. are as described in the herbicidal composition, which is one embodiment of the present application described above.

[0239]

[0240] Another aspect of the present application provides a method for controlling weeds in a cultivation field, comprising a step of treating the cultivation field with the nicotinamide compound or an agrochemically acceptable salt thereof and the phytoprotector together.

[0241] The above nicotinamide compound or its pesticide-acceptable salt and the laxative may be treated simultaneously or sequentially.

[0242] In one embodiment, the nicotinamide compound or its pesticide-acceptable salt and the laxative can be treated at a weight ratio of 1:0.05 to 1:20 (or 20:1 to 1:20), more specifically, 1:0.05 to 1:20, 1:0.05 to 1:10, 1:0.05 to 1:5, 1:0.05 to 1:4, 1:0.05 to 1:3, 1:0.05 to 1:2.75, 1:0.05 to 1:2.5, 1:0.05 to 1:2, 1:0.05 to 1:1.9, 1:0.05 to 1:1.88, 1:0.05 to 1:1.875, 1:0.05 to 1:1, 1:0.1 to 1:20, 1:0.1 to 1:10, 1:0.1 to 1:5, 1:0.1 to 1:4, 1:0.1 to 1:3, 1:0.1 to 1:2.75, 1:0.1 to 1:2.5, 1:0.1 to 1:2, 1:0.1 to 1:1.9, 1:0.1 to 1:1.88, 1:0.1 to 1:1.875, 1:0.1 to 1:1, 1:0.2 to 1:20, 1:0.2 to 1:10, 1:0.2 to 1:5, 1:0.2 to 1:4, 1:0.2 to 1:3, 1:0.2 to 1:2.75, 1:0.2 to 1:2.5, 1:0.2 to 1:2, 1:0.2 to 1:1.9, 1:0.2 to 1:1.88, 1:0.2 to 1:1.875, 1:0.2 to 1:1, 1:0.25 to 1:20, 1:0.25 to 1:10, 1:0.25 to 1:5, 1:0.25 to 1:4, 1:0.25 to 1:3, 1:0.25 to 1:2.75, 1:0.25 to 1:2.5, 1:0.25 to 1:2, 1:0.25 to 1:1.9, 1:0.25 to 1:1.88, 1:0.25 to 1:1.875, 1:0.25 to 1:1, 1:0.333 to 1:20 (or 3:1 to 1:20), 1:0.333 to 1:10 (or 3:1 to 1:10), 1:0.333 to 1:5 (or 3:1 to 1:5), 1:0.333 to 1:4 (or 3:1 to 1:4), 1:0.333 to 1:3 (or 3:1 to 1:3), 1:0.333 to 1:2.75 (or 3:1 to 1:2.75), 1:0.333 to 1:2.5 (or 3:1 to 1:2.5), 1:0.333 to 1:2 (or 3:1 to 1:2), 1:0.333 to 1:1.9 (or 3:1 to 1:1.9), 1:0.333 to 1:1.88 (or 3:1 to 1:1.9), 1:0.333 to 1:1.875 (or 3:1 to 1:1.875), 1:0.333 to 1:1 (or 3:1 to 1:1), 1:0.5 to 1:20, 1:0.5 to 1:10, 1:0.5 to 1:5, 1:0.5 to 1:4, 1:0.5 to 1:3, 1:0.5 to 1:2.75, 1:0.5 to 1:2.5, 1:0.5 to 1:2, 1:0.5 to 1:1.9, 1:0.5 to 1:1.88, 1:0.5 to 1:1.875, 1:0.5 to 1:1, 1:1 to 1:20, 1:1 to 1:10, 1:1 to 1:5, 1:1 to 1:4, 1:1 to 1:3, 1:1 to 1:2.75, 1:1 to 1:2.5, 1:1 The weight ratio may be, but is not limited to, 1:2, 1:1 to 1:1.9, 1:1 to 1:1.88, or 1:1 to 1:1.875. The weight ratio may be, but is not limited to, the weight ratio of the final processing amount.

[0243] In a method for controlling weeds in a cultivated field, comprising a step of treating the cultivated field with the nicotinamide compound or an agrochemically acceptable salt thereof and a pesticide, the contents of the nicotinamide compound or an agrochemically acceptable salt thereof and the pesticide, the pest, the plant, the weight ratio, the effective amount, the weight %, the treatment amount, etc. are the same as those described in the herbicidal composition and the method for controlling weeds, which are one embodiment of the present application.

[0244]

[0245] The present application relates to a herbicidal composition comprising a nicotinamide compound or an agrochemically acceptable salt thereof and a herbicidal reducer, and a weed control method using the same. When the herbicidal composition of the present application is used, the harm to useful crops can be reduced when using a nicotinamide compound or an agrochemically acceptable salt thereof with excellent herbicidal activity.

[0246]

[0247] Hereinafter, the present application will be described in more detail through examples. These examples are intended solely to illustrate the present application more specifically, and it will be apparent to those skilled in the art that the scope of the present application is not limited by these examples, in accordance with the gist of the present application.

[0248]

[0249] Example

[0250]

[0251] (Throughout this specification, "%" used to indicate the concentration of a particular substance is (weight / weight) % for solid / solid, (weight / volume) % for solid / liquid, and (volume / volume) % for liquid / liquid, unless otherwise stated.)

[0252]

[0253] Example 1: Synthesis of a nicotinamide compound having herbicidal activity

[0254] As a nicotinamide compound having herbicidal activity, N-(1-methyl-1H-tetrazol-5-yl)-2-(((2-methyl-2H-tetrazol-5-yl)methoxy)methyl)-6-(trifluoromethyl)nicotinamide was prepared according to the method described in Korean Patent No. 10-2632628 (registered on January 29, 2024) and the following, and named 'Gen1' or 'LK-22372'.

[0255]

[0256] Step 1) (E)-4-Ethoxy-1,1,1-trifluorobut-3-en-2-one

[0257] At -10 ~ -1˚C, a mixture of ethyl vinyl ether (75.2 ml, 0.785 mol) and pyridine (58 ml, 0.714 mol) was slowly added to trifluoroacetic anhydride (150 g, 0.714 mol) over 30 minutes. When a solid began to precipitate after about half of the addition, diethyl ether (150 ml) was added, and after the entire addition, diethyl ether (300 ml) was additionally added to dilute, and the mixture was gradually warmed to room temperature and stirred for 3 hours. When the reaction was complete, the precipitated solid was removed by filtration while washing thoroughly with diethyl ether, and the organic layer was washed with a 0.1 N aqueous hydrochloric acid solution and water, dried using anhydrous magnesium sulfate, and concentrated under reduced pressure. 116 g (97%) was obtained without further purification.

[0258]

[0259] Step 2) Ethyl 4-((2-methyl-2H-tetrazol-5-yl)methoxy)-3-oxobutanoate

[0260] (2-Methyl-2H-tetrazol-5-yl)methanol (16.3 g, 0.143 mol) was dissolved in anhydrous tetrahydrofuran (550 ml), and sodium hydride (60% in oil) (17.2 g, 0.43 mol) was added at 0 ˚C. The reaction mixture was stirred at 0 ˚C for 15 minutes, and ethyl chloroacetoacetate (23.4 ml, 0.172 mol) dissolved in anhydrous tetrahydrofuran (100 ml) was slowly added over 30 minutes. The reaction mixture was stirred at room temperature for 3 hours. When the reaction was complete, the solvent was removed under reduced pressure, and the remaining mixture was adjusted to pH 3 with 1 N aqueous hydrochloric acid solution, and extracted with ethyl acetate. The obtained organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography to obtain 29.4 g (85%) of the desired compound.

[0261] 1 H NMR (300 MHz, CDCl3) 4.89 (s, 2H), 4.39 (s, 3H), 4.33 (s, 2H), 4.22 (q,J= 7.2 Hz, 2H), 3.56 (s, 2H), 1.29 (t,J= 7.2 Hz, 3H)

[0262]

[0263] Step 3) Ethyl 2-(((2-methyl-2H-tetrazol-5-yl)methoxy)methyl)-6-(trifluoromethyl)nicotinate

[0264] Ethyl 4-((2-methyl-2H-tetrazol-5-yl)methoxy)-3-oxobutanoate (8.4 g, 34.7 mmol) obtained above was dissolved in acetic acid (50 ml), and (E)-4-ethoxy-1,1,1-trifluorobut-3-en-2-one (7.6 g, 45.1 mmol) and ammonium acetate (10.7 g, 138.8 mmol) were added. The reaction mixture was stirred at 110 ˚C for 4 hours. Upon completion of the reaction, the reaction mixture was cooled to room temperature, diluted with ethyl acetate, and washed with water. The obtained organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography to obtain 9.2 g (76%) of the desired compound.

[0265] 1 H NMR (300 MHz, CDCl3) δ 8.33 (d,J= 8.3 Hz, 1H), 7.72 (d,J= 8.3 Hz, 1H), 5.16 (s, 2H), 4.94 (s, 2H), 4.43 (q,J= 7.1 Hz, 2H), 4.37 (s, 3H), 1.42 (t,J= 7.1 Hz, 3H)

[0266]

[0267] Step 4) 2-(((2-methyl-2H-tetrazol-5-yl)methoxy)methyl)-6-(trifluoromethyl)nicotinic acid

[0268] Ethyl 2-(((2-methyl-2H-tetrazol-5-yl)methoxy)methyl)-6-(trifluoromethyl)nicotinate (9.5 g, 27.5 mmol) obtained above was dissolved in methanol (80 ml) and tetrahydrofuran (30 ml), and then 2N aqueous sodium hydroxide solution (27.5 ml, 55.0 mmol) was added. The reaction mixture was stirred at room temperature for 1 hour, and when the reaction was complete, the solvent was removed under reduced pressure, and the remaining mixture was adjusted to pH 3 by adding 1N aqueous hydrochloric acid solution, and extracted with ethyl acetate. The obtained organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. 7.0 g (80%) of the desired compound was obtained without further purification.

[0269] 1 H NMR (300 MHz, CDCl3) δ 8.42 (d,J= 8.0 Hz, 1H), 7.75 (d,J= 8.0 Hz, 1H), 5.19 (s, 2H), 4.98 (s, 2H), 4.35 (s, 3H)

[0270]

[0271] Step 5) N-(1-methyl-1H-tetrazol-5-yl)-2-(((2-methyl-2H-tetrazol-5-yl)methoxy)methyl)-6-(trifluoromethyl)nicotinamide

[0272] 2-(((2-Methyl-2H-tetrazol-5-yl)methoxy)methyl)-6-(trifluoromethyl)nicotinic acid (10 g, 31.54 mmol) obtained above was dissolved in acetonitrile (300 ml), and carbonyldiimidazole (10.2 g, 63.1 mmol) was added. After stirring at room temperature for 1 hour, 5-amino-1-methyl-1H-tetrazol (6.25 g, 63.1 mmol) and 1,8-diazabicyclo[5.4.0]undec-7-ene (16.5 ml, 110.3 mmol) were added, and the mixture was stirred at 50 ˚C for 2 hours. When the reaction was complete, the solvent was removed under reduced pressure, and the remaining mixture was adjusted to pH 3 with 1 N aqueous hydrochloric acid solution, and extracted with ethyl acetate. The obtained organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was purified by column chromatography to obtain 11.3 g (90%) of the desired compound.

[0273] 1 H NMR (300 MHz, CDCl3) δ 10.77 (brs, NH), 8.39 (d,J= 8.0 Hz, 1H), 7.85 (d,J= 8.0 Hz, 1H), 5.14 (s, 2H), 5.00 (s, 2H), 4.26 (s, 3H), 4.10 (s, 3H)

[0274]

[0275] Experimental Example 1: Comparison of the Damage Reduction Effects of Different Herbicides

[0276] Experimental Example 1-1. Preparation of compound solutions and comparative examples

[0277] For the sole treatment of the compound (Gen1, LK-22372) synthesized in the above-described Example 1, a 95% technical concentrate (TC) of Gen1 was diluted with a treatment solution to prepare a compound solution so that the final treatment amount of Gen1 was 50 g ai / ha, 100 g ai / ha, or 200 g ai / ha. The composition of the treatment solution is as follows: acetone (Daejung Chemicals, purity 99.5%) 33% (v / v), Tween-20 (Sigma-Aldrich, purity: as lauric acid; 53%) 1% (v / v), water 66% (v / v).

[0278] In addition, Gen1 and a safener, isoxadifen-ethyl (manufacturer: TCI, purchase amount 5 g, Cas no: 163520-33-0, product number: I0956, physical state: solid, purity: 98% or more, molecular weight: 295.34) were mixed at a weight ratio of 2:1, and diluted with the treatment solution (acetone 33% (v / v), Tween-20 1% (v / v), water 66% (v / v)) as described above so that the final treatment dose of isoxadifen-ethyl was 25 g ai / ha, 50 g ai / ha, or 100 g ai / ha (the final treatment dose of Gen1 was 50 g ai / ha, 100 g ai / ha, or 200 g ai / ha, respectively), to prepare a mixed solution formulation.

[0279]

[0280] Experimental Example 1-2. Crop Treatment

[0281] Surface area 330 cm 2After filling a square plastic pot with horticultural soil, corn (Gwangmyeongok) seeds stored in a low-temperature storage (4˚C) were sown and grown for 8 days under greenhouse conditions (average temperature 30 ± 5˚C, light / dark = 14 / 10 hours). When the corn grew to 2 leaves and 12 cm in height, the pesticides prepared in Experimental Example 1-1 were applied to the leaves using an automatic spraying method in a spray booth at an amount of 60 mL per treatment.

[0282]

[0283] Experimental Example 1-3. Weakness Evaluation

[0284] After treatment with the pesticide, the plants were managed under the same greenhouse conditions as above, and the degree of damage on the 4th, 7th, 13th, and 21st days after treatment was evaluated on a scale of 0 to 9. The criteria for setting the grades are shown in Table 1 below.

[0285] Grade Weakness Degree 0 When no weakness occurs 1 When there is a difference in appearance due to slight weak spots, leaf discoloration, etc., but there is no significant difference 2 When there are some symptoms such as weak spots, discoloration, and growth inhibition due to some weakness, but they quickly recover and do not affect growth 3 When there are clear weakness symptoms such as leaf curl, growth inhibition, and abnormal symptoms, recovery is slow and growth is somewhat affected, but there is no effect on yield 4 When leaf curl, discoloration, weak spots, growth inhibition, and abnormal growth are severe and recovery is uncertain or a reduction of 5% or less is expected 5 When recovery is doubtful and a reduction of about 10% is expected 6 When weakness continues and a reduction of about 15% is expected 7 When weakness is severe and a reduction of about 20% is expected 8 When weakness is severe and a reduction of about 30% is expected 9 When weakness is severe and a reduction of more than 50% is expected

[0286]

[0287] Experimental Example 1-4. Weakness Evaluation Results

[0288] The results of evaluating the degree of weakness are shown in Table 2 below. Three replicate values ​​are shown for each treatment group.

[0289] Treatment substanceHerbicidal substanceFinal treatment amount(g ai / ha)Weakness after treatment (grade 0 to 9)Day 4Day 7Day 13Day 21Gen1 95% TC50.0433143314331100.0436644644464200.0558854755475Gen1 95% TC and isoxadiphen-ethyl (2:1 weight ratio)50.0(isoxadiphen-ethyl 25.0)211011102110100.0(isoxadiphen-ethyl 50.0)211021102110200.0(isoxadiphen-ethyl 100.0)211021102110

[0290] As shown in Table 2, when Gen1 was used on corn, phytotoxicity was observed, and when Gen1 and isoxadiphen-ethyl were mixed, it was confirmed that phytotoxicity was significantly reduced.

[0291]

[0292] Experimental Example 2: Comparison of the hazard mitigation effects of different hazard mitigants.

[0293] Experimental Example 2-1. Preparation of compound solution

[0294] To confirm the difference in the degree of toxicity reduction according to the toxicity reduction agent used in combination with Gen1, the following experiment was conducted.

[0295] For the sole treatment of the compound (Gen1, LK-22372) synthesized in the above-described Example 1, a 95% original solution (technical concentrate, TC) of Gen1 was diluted with the treatment solution described in Experimental Example 1-1 so that the final treatment amount of the experimental compound was 37.5 g ai / ha, thereby preparing a compound solution.

[0296] In addition, a mixed solution formulation was prepared by diluting with the treatment solution described in Experimental Example 1-1 so that the final treatment amount of Gen1 and the safener were mixed at a final treatment weight ratio of 1:2, so that the final treatment amount of Gen1 was 37.5 g ai / ha, and the final treatment amount of the safener was 75 g ai / ha. The laxatives used were mefenpyr-diethyl (manufacturer: Sigma-aldrich, purchase volume 100 mg, Cas no: 135590-91-9, product number: 46302, physical state: solid, purity: 98% or more, molecular weight: 373.23), isoxadifen-ethyl (manufacturer: TCI, purchase volume 5 g, Cas no: 163520-33-0, product number: I0956, physical state: solid, purity: 98% or more, molecular weight: 295.34), dichlormid (manufacturer: TCI, purchase volume 5 g, Cas no: 37764-25-3, product number: D3397, physical state: liquid, purity: 97% or more, molecular weight: 208.08) and benoxacor (Manufacturer: Sigma-aldrich, Purchased amount 100 mg, Cas no: 98730-04-2, Product number: 46001, Physical state: Solid, Purity: 98% or more, Molecular weight: 260.12).

[0297]

[0298] Experimental Example 2-2. Crop Treatment

[0299] Surface area 330 cm 2After filling the square plastic pots with horticultural soil, corn seeds (K-pop (popcorn), Heukjinjuchal (waxy corn), and Chodang (for reproduction)) stored in a low-temperature storage (4˚C) were sown by variety and grown under greenhouse conditions (average temperature 30 ± 5˚C, light / dark = 14 / 10 hours) for 8 days for K-pop, 7 days for Heukjinjuchal, and 8 days for Chodang. The number of leaves and leaf size at the time of treatment are shown in Table 3 below. The pesticides prepared in Experimental Example 2-1 were applied to the foliage using an automatic spray method in a spray booth at an amount of 60 mL per treatment.

[0300]

[0301] Experimental Example 2-3. Weakness Evaluation

[0302] After treatment with the drug, the plants were managed under the same greenhouse conditions as above, and the degree of damage on the 5th and 10th days after treatment was evaluated using the methods described in Experimental Example 1-3 and Table 1.

[0303]

[0304] Experimental Example 2-4. Results of the weakness evaluation

[0305] The results of evaluating the degree of damage to each corn variety are shown in Table 3 below.

[0306] Treatment substance Herbicidal substance Final treatment amount (g ai / ha) After treatment Weak K-pop Black Pearl Chal 1.5~1.6 leaves per second 1.8~2 leaves 1.5 leaves 14~15 cm 16~17 cm 14~15 cm Day 5 Day 10 Day 5 Day 10 Day 5 Day 10 Gen1 37.5 5 4 6 5 4 Gen1 and mefenpyr-diethyl (1:2 weight ratio) 37.5 (mefenpyr-diethyl 75) 5 3 6 4 4 Gen1 and isoxadiphen-ethyl (1:2 weight ratio) 37.5 (isoxadiphen-ethyl 75) 1 1 1 0 Gen1 and dichloride (1:2 weight ratio) 37.5 (dichloride 75) 5 3 6 5 4 Gen1 and benoxacol (1:2 weight ratio) 37.5 (benoxacol) 75)334344

[0307] As shown in Table 3, when Gen1 was used in combination with isoxadifen-ethyl, the toxicity was significantly alleviated, whereas when mefenpyr-diethyl or benoxacol was used in combination, there was no significant difference in the degree of toxicity, confirming that no significant toxicity alleviation effect was observed.

[0308]

[0309] Experimental Example 3: Comparison of the Effects of Weakness Reduction on Different Crop Types

[0310] Experimental Example 3-1. Preparation of compound solution

[0311] For the sole treatment of the compound (Gen1, LK-22372) synthesized in the above-described Example 1, a 95% original solution (technical concentrate, TC) of Gen1 was diluted with the treatment solution described in Experimental Example 1-1 so that the final treatment amount of the experimental compound was 50 g ai / ha, 100 g ai / ha, or 200 g ai / ha, thereby preparing a compound solution.

[0312] In addition, Gen1 and isoxadifen-ethyl, a safener, were mixed in a ratio of 2:1, and a mixed solution formulation was prepared by diluting with the treatment solution described in Experimental Example 1-1 so that the final treatment dose of Gen1 was 50 g ai / ha, 100 g ai / ha, or 200 g ai / ha (the final treatment dose of isoxadifen-ethyl was 25 g ai / ha, 50 g ai / ha, or 100 g ai / ha, respectively).

[0313]

[0314] Experimental Example 3-2. Crop Treatment

[0315] Surface area 330 cm 2After filling the square plastic pots with horticultural soil, corn seeds (Gwangmyeongok (for feed), K-pop (popcorn), Heukjinjuchal (glutinous corn), and Chodang (for eating)) stored in a low-temperature storage (4˚C) were sown by variety and grown under greenhouse conditions (average temperature 30 ± 5˚C, light / dark = 14 / 10 hours) for 7 days for Gwangmyeongok, 8 days for K-pop, 6 days for Heukjinjuchal, 9 days for Chodang, 13 days for mid-sized seedlings, and 6 days for young seedlings. The number of leaves and plant height during treatment are shown in Table 3 below. The pesticides prepared in Experimental Example 2-1 were applied to the foliage using an automatic spray method in a spray booth at an amount of 60 mL per treatment.

[0316]

[0317] Experimental Example 3-3. Weakness Evaluation

[0318] After treatment with the drug, the plants were managed under the same greenhouse conditions as above, and the degree of damage on the 5th, 11th, and 15th days after treatment was evaluated using the methods described in Experimental Example 1-3 and Table 1.

[0319]

[0320] Experimental Example 3-4. Results of the weakness evaluation

[0321] The results of evaluating the degree of damage to corn are shown in Table 4 below.

[0322] Treatment substance Herbicidal substance Final treatment amount (g ai / ha) After treatment Weak Gwangmyeongok (forage) K-pop (popcorn) 3 leaves, 22 cm 3 leaves, 20 cm Day 5 Day 11 Day 15 Day 5 Day 11 Day 15 Gen1 95% TC 50.0 332443332455332445 100.05 34466556477555477 200.04 66N / A87 567N / A88N / A67N / A77 Gen1 95% TC and isoxadiphen-ethyl (2:1 weight ratio) 50.0 (isoxadiphen-ethyl 25.0) 1112 101112 102112 10100.0 (isoxadiphen-ethyl) 50.0)211210211321211311200.0(Isoxadiphen-ethyl 100.0)322N / A32322N / A44N / A32N / A23-Black Pearl Chal (Wicked Corn) per second (for raw food) 2 leaves, 19 cm 3 leaves, 21 cm Day 5 Day 11 Day 15 Day 5 Day 11 Day 15 Gen1 95% TC 50.0343364364364365364 100.0564N / A774754N / A64764N / A7200.0478N / AN / AN / A588N / AN / AN / AN / A88N / AN / A8 Gen1 95% TC and isoxadiphen-ethyl (2:1) Weight ratio) 50.0 (isoxadiphene-ethyl 25.0) 210 22 12 10 22 12 10 22 11 00.0 (isoxadiphene-ethyl 50.0) 220 N / A 3 22 10 3 N / A 1 2 1 3 N / A 2 20 0.0 (isoxadiphene-ethyl 100.0) 321 N / AN / AN / A 3 21 N / AN / AN / AN / A 2 1 N / AN / A 4

[0323] As shown in Table 4, it was confirmed that all varieties (Gwangmyeongok, K-pop, Heukjinjuchal, and Chodang) showed a phytotoxicity reduction effect when Gen1 and isoxadifen-ethyl were mixed and treated. In particular, the most remarkable phytotoxicity reduction effect was observed in Gwangmyeongok, a feed corn variety, on the 5th day after treatment, and on the 11th day after treatment, a remarkable phytotoxicity reduction effect was observed in all varieties of Gwangmyeongok, K-pop, and Heukjinjuchal, indicating that the phytotoxicity reduction effect was amplified in varieties with fast growth and strong recovery.

[0324]

[0325] Experimental Example 4: Comparison of the pest control effects of herbicides and pest control agents by weight ratio.

[0326] Through the above experiment, it was confirmed that the combined treatment of Gen1 and isoxadiphen-ethyl had an excellent toxicity reduction effect. Therefore, the following experiment was conducted to confirm the toxicity reduction effect by treatment amount and weight ratio.

[0327]

[0328] Experimental Example 4-1: Comparison of the pest reduction effects of herbicides and pest control agents by weight ratio (1)

[0329] For the sole treatment of the compound (Gen1, LK-22372) synthesized in the above-described Example 1, a 95% original (technical concentrate, TC) of Gen1 was diluted with the treatment solution described in Experimental Example 1-1 so that the final treatment amount of the experimental compound was the amount described in Tables 5 to 7 below, respectively, to prepare a compound solution.

[0330] In addition, a mixed solution formulation was prepared by diluting with the treatment solution described in Experimental Example 1-1 so that the final treatment weight ratio and final treatment amount of Gen1 and the safener were as described in Tables 5 to 7 below, respectively.

[0331] After that, surface area 330 cm 2 After filling the square plastic pots with horticultural soil, corn seeds (Gwangmyeongok (for feed), K-Pop (popcorn), Heukjinjuchal (glutinous corn), and Chodang (for eating)) stored in a low-temperature storage (4˚C) were sown by variety and grown under greenhouse conditions (average temperature 30 ± 5˚C, light / dark = 14 / 10 hours). The number of leaves and plant height during treatment are shown in Tables 5 to 7, respectively. The pesticides prepared in Experimental Example 2-1 were applied to the foliage using an automatic spray method in a spray booth at an amount of 60 mL per treatment.

[0332] After treatment with the drug, the plants were managed under the same greenhouse conditions as above, and the degree of damage at the time of treatment was evaluated using the methods described in Experimental Example 1-3 and Table 1. The evaluation results are shown in Tables 5 to 7 below.

[0333] Treatment material (weight ratio) Herbicidal substance Final treatment amount (g ai / ha) After treatment Yakhae Gwangmyeongok (for feed) Per second (for raw food) K-pop (for popcorn) 2.8~3 leaves 2.5~2.7 leaves 2.8~3 leaves 20~22 cm 17~18 cm 18~19 cm m Day 5 Day 10 Day 19 Day 5 Day 10 Day 19 Day 5 Day 10 Day 19 Gen1 60 34 36 7 6 6 7 5 Gen1 and isoxadiphen-ethyl (1:1.67 weight ratio) 60 (isoxadiphen-ethyl 100) 000 22 0 32 0 Gen1 and isoxadiphen-ethyl (1:2.5 weight ratio) 60 (isoxadiphen-ethyl 150) 000 22 0 32 0

[0334] As shown in Table 5, it was confirmed that a remarkable phytotoxicity reduction effect was observed in both cases where the final treatment weight ratio of Gen1 and the phytotoxicity reducing agent was 1:1.67 and 1:2.5. More specifically, in the case of Gwangmyeongok, the phytotoxicity levels were all grade 1 or lower, in the case of Chodang, the phytotoxicity levels were all grade 2 or lower, and it was confirmed that it was reduced by more than 4 grades compared to the Gen 1 treatment alone, and in the case of K-pop, it was confirmed that the phytotoxicity levels were reduced by 3 to 5 grades.

[0335]

[0336] Treatment material (weight ratio) Herbicidal material Final treatment amount (g ai / ha) After treatment, weak K-pop black pearl chalcedony 2 leaves 1.5~1.7 leaves 1.5 leaves 1.8~2 leaves 13~14 cm 13~14 cm 14~15 cm 13~14 cm 5 days 11 days 5 days 11 days 5 days 11 days 5 days 11 days Gen 1 37.5 6 5 5 5 6 4 3 3 Gen 1 and isoxadiphen-ethyl (1:2 weight ratio) 37.5 (isoxadiphen-ethyl 75) 10 10 10 11

[0337] As shown in Table 6, when the final treatment weight ratio of Gen1 and the pest control agent was 1:2, the pest control level was grade 1 or lower in all varieties, confirming a significant pest control effect.

[0338]

[0339] Treatment material (weight ratio) Herbicidal material Final treatment amount (g ai / ha) After treatment Weak K-pop Black Pearl Chalchodang Gwangmyeong 1.5~1.6 leaves 1.8~2 leaves 1.5 leaves 1 leaf 14~15 cm 16~17 cm 14~15 cm 8~9 cm 11th day 11th day 11th day 11th day Gen1 100 8774 Gen1 and isoxadiphen-ethyl (1:1 weight ratio) 100 (isoxadiphen-ethyl 100) 2201 Gen1 and isoxadiphen-ethyl (1:2 weight ratio) 100 (isoxadiphen-ethyl 200) 1101 Gen1 and isoxadiphen-ethyl (1:3 weight ratio) 100 (isoxadiphen-ethyl 300) 1101 Gen1 and isoxadiphen-ethyl (2:1 (Weight ratio) 100 (Isoxadiphen-ethyl 50) 4211Gen1 and isoxadiphen-ethyl (3:1 weight ratio) 100 (Isoxadiphen-ethyl 33.3) 3312

[0340] As shown in Table 7, in all cases where the final treatment weight ratio of Gen1 and the phytosanitizer was 1:1, 1:2, 1:3, 2:1, and 3:1, the phytosanitary degree was either grade 3 or lower, or was reduced by at least 4 grades compared to Gen 1 treatment alone, demonstrating a remarkable phytosanitary degree reduction effect. In particular, in cases where the final treatment weight ratio was 1:1, 1:2, or 1:3, the phytosanitary degree was all grade 2 or lower, demonstrating an even more outstanding phytosanitary degree reduction effect.

[0341]

[0342] Experimental Example 4-2: Comparison of the pest reduction effects of herbicides and pest control agents by weight ratio (2)

[0343] For the sole treatment of the compound (Gen1, LK-22372) synthesized in Example 1 described above, the Gen1 290 SL product (Gen1 26% w / w SL) was diluted with the treatment solution to prepare a compound solution formulation so that the final treatment amount of Gen1 was 25 g ai / ha, 50 g ai / ha, or 100 g ai / ha. The composition of the treatment solution is as follows: MSO (Yuseong Chemical Technology Co., Ltd., Fatty acids, soya, Me esters 88-92%, CAS No. 68919-53-9) 1% (v / v), water 99% (v / v).

[0344] In addition, a mixed solution formulation was prepared by diluting Gen1 42 EC product (Gen1+Isoxadifen-ethyl 4+7.5% w / w SL) with the treatment solution so that the final treatment weight ratio of Gen1 and isoxadifen-ethyl was 1:1.875. The treatment solutions were prepared so that the final treatment doses of Gen1 were 25 g ai / ha, 50 g ai / ha, or 100 g ai / ha, respectively, and the treatment doses of isoxadifen-ethyl were 46.875 g ai / ha, 93.75 g ai / ha, and 187.5 g ai / ha, respectively. The composition of the treatment solution is as follows: MSO (Yuseong Chemical Technology Co., Ltd., Fatty acids, soya, Me esters 88 ~ 92%, CAS No. 68919-53-9) 1% (v / v), water 99% (v / v).

[0345] After that, surface area 330 cm 2 After filling the square plastic pots with horticultural soil, corn (Gwangmyeongok) seeds stored in a low-temperature storage (4˚C) were sown by variety and grown under greenhouse conditions (average temperature 30 ± 5˚C, light / dark = 14 / 10 hours). The number of leaves and plant height during treatment are shown in Table 8 below. The pesticides prepared in Experimental Example 2-1 were applied to the foliage using an automatic spray method in a spray booth at an amount of 60 mL per treatment.

[0346] After treatment with the drug, the plants were managed under the same greenhouse conditions as above, and the degree of damage at the time of treatment was evaluated using the method described in Experimental Example 1-3 and Table 1. The evaluation results are shown in Table 8 below.

[0347] Treatment substance Herbicidal substance Final treatment amount (g ai / ha) After treatment, weak light ok 1~.1.5 leaf 7~8 cm 8 DA AG en 1 2 5 2 5 0 3 1 0 0 4 Gen 1 and isoxadiphen-ethyl (1:1.875 weight ratio) 2 5 (isoxadiphen-ethyl 46.875) 0 5 0 (isoxadiphen-ethyl 93.75) 0 1 0 0 (isoxadiphen-ethyl 187.5) 0

[0348] As shown in Table 8, when Gen1 was used alone, phytotoxicity occurred, but when Gen1 and isoxadiphen-ethyl were mixed in a weight ratio of 1:1.875, phytotoxicity did not occur in the entire final treatment amount range of Gen1, a herbicidal substance, confirming an excellent phytotoxicity reduction effect.

[0349]

[0350] Experimental Example 5. Packaging Test

[0351] In the above Experimental Example 4-2, when Gen1 and isoxadiphen-ethyl were mixed and used in a weight ratio of 1:1.875, it was confirmed that there was a significant weakening effect, and this was verified in the packaging test stage.

[0352] The final treatment doses of Gen1 in 100 to 200 L of water per Ha were 25 g ai / ha, 30 g ai / ha, 35 g ai / ha, 50 g ai / ha, 60 g ai / ha, and 70 g ai / ha, respectively, in the same manner as in Experimental Example 4-2, and the weight ratio of the final treatment doses of Gen1 and isoxadiphen-ethyl was prepared to be approximately 1:1.875, and the treatment solution was treated by mixing 1% v / v MSO with respect to the water amount. The pesticide was evaluated for six types of corn in the five regions of the United States listed in Table 9, and the pesticide was applied when the corn grew to 4 to 6 leaves or 13 cm to 40 cm, and the degree of pesticide was evaluated on the 6th to 7th day and 14th to 15th day by the method described in Experimental Example 1-3 and Table 1. The results are shown in Table 9.

[0353]

[0354] As shown in Table 9, in the field tests conducted in Fisk, Columbia, Clontarf, and Aurora, the degree of phytotoxicity was observed to be 0 in all cases, confirming that when Gen1 and isoxadiphen-ethyl are mixed in a weight ratio of 1:1.875, it can be confirmed that it can be used safely because it has an excellent phytotoxicity reduction effect in pop corn and sweet corn. In the test conducted on field corn and pop corn in York, slight phytotoxicity of 0 to 2 occurred, but this was at a level that quickly recovered and did not affect the yield. In this test as well, it was confirmed that when Gen1 and isoxadiphen-ethyl are mixed in a weight ratio of 1:1.875, it has an excellent phytotoxicity reduction effect in field corn and pop corn, and it can be used safely.

Claims

1. A nicotinamide compound represented by the following chemical formula 1 or an agrochemically acceptable salt thereof [Chemical Formula 1] ; and A herbicidal composition comprising at least one laxative selected from the group consisting of isoxadifen-ethyl, benoxacor, dichlormid, and mefenpyr-diethyl: In the above chemical formula 1, A is or represents; B is or represents; X represents O or S; Y represents O, S, SO, SO2, NH, N-(C1-C6)-alkyl group, N-(C2-C6)-alkenyl group, N-(C2-C6)-alkynyl group, NO-(C1-C6)-alkyl group, NS-(C1-C6)-alkyl group, NS(O)-(C1-C6)-alkyl group, N-SO2-(C1-C6)-alkyl group, NO-(C1-C3)-alkyl-aryl group or hydroxylamino group; Z represents N or C-R8; R1 represents a (C1-C6)-alkyl group, a (C1-C6)-haloalkyl group, a (C2-C6)-alkenyl group, a (C2-C6)-haloalkenyl group, a (C2-C6)-alkynyl group, a (C2-C6)-haloalkynyl group, a (C3-C6)-cycloalkyl group or a (C3-C6)-halocycloalkyl group; R2 represents hydrogen, a (C1-C6)-alkyl group, a (C1-C6)-haloalkyl group, a (C2-C6)-alkenyl group, a (C2-C6)-haloalkenyl group, a (C2-C6)-alkynyl group, a (C2-C6)-haloalkynyl group, a C(O)-(C1-C6)-alkyl group, a C(O)aryl group, a C(O)heteroaryl group, or a SO2-(C1-C6)-alkyl group; R3 and R4 each independently represent hydrogen, a halogen group, a (C1-C6)-alkyl group, a (C2-C6)-alkenyl group, or a (C3-C6)-cycloalkyl group; R5 represents a halogen group, a (C1-C3)-alkyl group or a (C1-C3)-haloalkyl group; R6 represents a (C1-C6)-alkyl group, a (C1-C6)-haloalkyl group, a (C2-C6)-alkenyl group, a (C2-C6)-haloalkenyl group, a (C2-C6)-alkynyl group, a (C2-C6)-haloalkynyl group, a (C3-C6)-cycloalkyl group, a (C3-C6)-halocycloalkyl group, a (C1-C3)-alkyl-O-(C1-C3)-alkyl group or a (C1-C3)-alkyl-S-(C1-C3)-alkyl group; R7 represents a (C1-C6)-alkyl group, a (C1-C6)-haloalkyl group, a (C3-C6)-cycloalkyl group or a (C3-C6)-halocycloalkyl group; R8 is hydrogen, (C1-C6)-alkyl group, (C1-C6)-haloalkyl group, (C2-C6)-alkenyl group, (C2-C6)-haloalkenyl group, (C2-C6)-alkynyl group, (C2-C6)-haloalkynyl group, (C3-C6)-cycloalkyl group, (C3-C6)-halocycloalkyl group, (C1-C6)-alkoxy group, (C1-C6)-haloalkoxy group, (C1-C6)-alkylthio group, (C1-C6)-haloalkylthio group, S(O)-(C1-C6)-alkyl group, S(O)-(C1-C6)-haloalkyl group, SO2-(C1-C6)-alkyl group, SO2-(C1-C6)-haloalkyl group, NR9R 10 , representing a cyano group or a halogen group; R9 or R 10 independently represents hydrogen, a (C1-C3)-alkyl group or a (C1-C3)-haloalkyl group; n and m each independently represent 0, 1, or 2.

2. In paragraph 1, The above A is or represents; The above B is or represents; wherein X represents O or S; The above Y represents O, S, SO, SO2, NH, N-(C1-C3)-alkyl group, N-(C2-C6)-alkynyl group, NO-(C1-C3)-alkyl group, NO-(C1-C3)-alkyl-aryl group or hydroxylamino group; wherein Z represents N or C-R8; The above R1 represents a (C1-C6)-alkyl group, a (C1-C6)-haloalkyl group, a (C2-C6)-alkenyl group or a (C2-C6)-alkynyl group; The above R2 represents hydrogen, a (C1-C3)-alkyl group, a (C1-C3)-haloalkyl group, a C(O)-(C1-C6)-alkyl group, a C(O)aryl group, or a SO2-(C1-C3)-alkyl group; The above R3 and R4 each independently represent hydrogen, a halogen group, a (C1-C6)-alkyl group or a (C2-C6)-alkenyl group; The above R5 represents a halogen group or a (C1-C3)-haloalkyl group; The above R6 represents a (C1-C6)-alkyl group, a (C1-C6)-haloalkyl group or a (C1-C3)-alkyl-O-(C1-C3)-alkyl group; The above R7 represents a (C1-C6)-alkyl group or a (C3-C6)-cycloalkyl group; The above R8 is hydrogen, (C1-C3)-alkyl group, (C1-C6)-haloalkyl group, (C2-C6)-alkenyl group, (C1-C3)-alkoxy group, (C1-C3)-haloalkoxy group, (C1-C3)-alkylthio group, SO2-(C1-C3)-alkyl group, NR9R 10 , representing a cyano group or a halogen group; The above R9 or R 10 independently represents hydrogen or a (C1-C3)-alkyl group; wherein n represents 0 or 1; A herbicidal composition, wherein the above m represents 0, 1 or 2.

3. In paragraph 1, The above A is or represents; The above B is or represents; wherein X represents O or S; The above Y represents O, S, SO, SO2, NH, a methylamino group, an ethylamino group, a propargylamino group, a benzyloxyamino group, a methoxyamino group, an ethoxyamino group or a hydroxylamino group; wherein Z represents N or C-R8; The above R1 represents a methyl group, an ethyl group, an n-propyl group, a difluoromethyl group, an allyl group or a propargyl group; The above R2 represents hydrogen, a methyl group, an acetyl group, a benzoyl group, or a methanesulfonyl group; The above R3 and R4 each independently represent hydrogen, chlorine, bromine, iodine, a methyl group, an ethyl group or a vinyl group; The above R5 represents chlorine, difluoromethyl group, trifluoromethyl group, chlorodifluoromethyl group or perfluoroethyl group; The above R6 represents a methyl group, an ethyl group, a difluoromethyl group or a methoxymethyl group; The above R7 represents a methyl group, an ethyl group, an isopropyl group or a cyclohexyl group; The above R8 represents hydrogen, a methyl group, a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, an ethenyl group, a methylethenyl group, a methoxy group, a trifluoroethoxy group, a methylthio group, a methanesulfonyl group, a dimethylamino group, a cyano group, chlorine, bromine or iodine; wherein n represents 0 or 1; A herbicidal composition, wherein the above m represents 0, 1 or 2.

4. In the first paragraph, the herbicidal composition, wherein the nicotinamide compound or an agrochemically acceptable salt thereof is selected from the group consisting of: (1)N-(1-methyl-1H-tetrazol-5-yl)-2-((1-methyl-1H-tetrazol-5-yl)methoxy)-6-(trifluoromethyl)nicotinamide; (2)N-(1-(difluoromethyl)-1H-tetrazol-5-yl)-2-((1-methyl-1H-tetrazol-5-yl)methoxy)-6-(trifluoromethyl)nicotinamide; (3) 2-((1-(difluoromethyl)-1H-tetrazol-5-yl)methoxy)-N-methyl-N-(1-methyl-1H-tetrazol-5-yl)-6-(trifluoromethyl)nicotinamide; (4) 4-chloro-N-(1-methyl-1H-tetrazol-5-yl)-2-((1-methyl-1H-tetrazol-5-yl)methoxy)-6-(trifluoromethyl)nicotinamide; (5) 5-methyl-N-(1-methyl-1H-tetrazol-5-yl)-2-((1-methyl-1H-tetrazol-5-yl)methoxy)-6-(trifluoromethyl)nicotinamide; (6)N-(1-methyl-1H-tetrazol-5-yl)-2-((1-methyl-1H-tetrazol-5-yl)methoxy)-6-(trifluoromethyl)-5-vinylnicotinamide; (7) 5-ethyl-N-(1-methyl-1H-tetrazol-5-yl)-2-((1-methyl-1H-tetrazol-5-yl)methoxy)-6-(trifluoromethyl)nicotinamide; (8) 6-chloro-N-(1-methyl-1H-tetrazol-5-yl)-2-((1-methyl-1H-tetrazol-5-yl)methoxy)nicotinamide; (9) 2-((1-(difluoromethyl)-1H-tetrazol-5-yl)methoxy)-N-(1-methyl-1H-tetrazol-5-yl)-6-(trifluoromethyl)nicotinamide; (10) 2-(methyl((1-methyl-1H-tetrazol-5-yl)methyl)amino)-N-(1-methyl-1H-tetrazol-5-yl)-6-(trifluoromethyl)nicotinamide; (11)N-(1-methyl-1H-tetrazol-5-yl)-2-((1-methyl-1H-tetrazol-5-yl)thio)-6-(trifluoromethyl)nicotinamide; (12)N-(1-methyl-1H-tetrazol-5-yl)-2-((1-methyl-1H-tetrazol-5-yl)methoxy)-6-(trifluoromethyl)pyridine-3-carbothioamide; (13) 2-((1-methyl-1H-1,2,4-triazol-5-yl)methoxy)-N-(1-methyl-1H-tetrazol-5-yl)-6-(trifluoromethyl)nicotinamide; (14)N-(1-methyl-1H-tetrazol-5-yl)-2-(((1-methyl-1H-tetrazol-5-yl)methoxy)methyl)-6-(trifluoromethyl)nicotinamide; (15) 2-(((1-(difluoromethyl)-1H-tetrazol-5-yl)methoxy)methyl)-N-(1-methyl-1H-tetrazol-5-yl)-6-(trifluoromethyl)nicotinamide; (16) 2-((methyl((1-methyl-1H-tetrazol-5-yl)methyl)amino)-N-((1-methyl-1H-tetrazol-5-yl)-6-(trifluoromethyl)nicotinamide; (17) 2-((methoxy((1-methyl-1H-1,2,4-triazol-5-yl)methyl)amino)methyl)-N-(1-methyl-1H-tetrazol-5-yl)-6-(trifluoromethyl)nicotinamide; (18)N-(1-methyl-1H-tetrazol-5-yl)-2-(((1-methyl-1H-tetrazol-5-yl)thio)methyl)-6-(trifluoromethyl)nicotinamide; (19) 2-(((1-methyl-1H-1,2,4-triazol-5-yl)methoxy)methyl)-N-(1-methyl-1H-tetrazol-5-yl)-6-(trifluoromethyl)nicotinamide; (20)N-(1-methyl-1H-tetrazol-5-yl)-2-(((1-methyl-1H-tetrazol-5-yl)oxy)methyl)-6-(trifluoromethyl)nicotinamide; (21)N-(1-methyl-1H-tetrazol-5-yl)-2-((2-methyl-2H-tetrazol-5-yl)methoxy)-6-(trifluoromethyl)nicotinamide; (22) 2-(methyl((2-methyl-2H-tetrazol-5-yl)methyl)amino)-N-(1-methyl-1H-tetrazol-5-yl)-6-(trifluoromethyl)nicotinamide; (23) 2-(ethyl((2-methyl-2H-tetrazol-5-yl)methyl)amino)-N-(1-methyl-1H-tetrazol-5-yl)-6-(trifluoromethyl)nicotinamide; (24)N-(1-methyl-1H-tetrazol-5-yl)-2-(((2-methyl-2H-tetrazol-5-yl)methyl)(prop-2-yn-1-yl)amino)-6-(trifluoromethyl)nicotinamide; (25) 2-((benzyloxy)((2-methyl-2H-tetrazol-5-yl)methyl)amino)-N-(1-methyl-1H-tetrazol-5-yl)-6-(trifluoromethyl)nicotinamide; (26) 2-(methoxy((2-methyl-2H-tetrazol-5-yl)methyl)amino)-N-(1-methyl-1H-tetrazol-5-yl)-6-(trifluoromethyl)nicotinamide; (27) 2-(Ethoxy((2-methyl-2H-tetrazol-5-yl)methyl)amino)-N-(1-methyl-1H-tetrazol-5-yl)-6-(trifluoromethyl)nicotinamide; (28)N-(1-methyl-1H-tetrazol-5-yl)-2-(((2-methyl-2H-tetrazol-5-yl)methyl)amino)-6-(trifluoromethyl)nicotinamide; (29) 2-(hydroxy((2-methyl-2H-tetrazol-5-yl)methyl)amino)-N-(1-methyl-1H-tetrazol-5-yl)-6-(trifluoromethyl)nicotinamide; (30) 2-(methyl((1-methyl-1H-1,2,4-triazol-3-yl)methyl)amino)-N-(1-methyl-1H-tetrazol-5-yl)-6-(trifluoromethyl)nicotinamide; (31) 2-(methyl(2-(2-methyl-2H-tetrazol-5-yl)ethyl)amino)-N-(1-methyl-1H-tetrazol-5-yl)-6-(trifluoromethyl)nicotinamide; (32) 2-((1-methyl-1H-1,2,4-triazol-3-yl)methoxy)-N-(1-methyl-1H-tetrazol-5-yl)-6-(trifluoromethyl)nicotinamide; (33)N-(1-methyl-1H-tetrazol-5-yl)-2-(((2-methyl-2H-tetrazol-5-yl)methoxy)methyl)-6-(trifluoromethyl)nicotinamide; (34)N-acetyl-N-(1-methyl-1H-tetrazol-5-yl)-2-(((2-methyl-2H-tetrazol-5-yl)methoxy)methyl)-6-(trifluoromethyl)nicotinamide; (35)N-Benzoyl-N-(1-methyl-1H-tetrazol-5-yl)-2-(((2-methyl-2H-tetrazol-5-yl)methoxy)methyl)-6-(trifluoromethyl)nicotinamide; (36)N-(1-methyl-1H-tetrazol-5-yl)-2-(((2-methyl-2H-tetrazol-5-yl)methoxy)methyl)-N-(methylsulfonyl)-6-(trifluoromethyl)nicotinamide; (37) 6-(Chlorodifluoromethyl)-N-(1-methyl-1H-tetrazol-5-yl)-2-(((2-methyl-2H-tetrazol-5-yl)methoxy)methyl)nicotinamide; (38) 6-(Chlorodifluoromethyl)-2-((methoxy((2-methyl-2H-tetrazol-5-yl)methyl)amino)methyl)-N-(1-methyl-1H-tetrazol-5-yl)nicotinamide; (39) 6-(Chlorodifluoromethyl)-2-(((1-methyl-1H-1,2,4-triazol-3-yl)methoxy)methyl)-N-(1-methyl-1H-tetrazol-5-yl)nicotinamide; (40)N-(1-methyl-1H-tetrazol-5-yl)-2-(((2-methyl-2H-tetrazol-5-yl)methoxy)methyl)-6-(perfluoroethyl)nicotinamide; (41) 2-(((1-methyl-1H-1,2,4-triazol-3-yl)methoxy)methyl)-N-(1-methyl-1H-tetrazol-5-yl)-6-(perfluoroethyl)nicotinamide; (42) 6-(Difluoromethyl)-N-(1-methyl-1H-tetrazol-5-yl)-2-(((2-methyl-2H-tetrazol-5-yl)methoxy)methyl)nicotinamide; (43) 6-(Difluoromethyl)-2-(((1-methyl-1H-1,2,4-triazol-3-yl)methoxy)methyl)-N-((1-methyl-1H-tetrazol-5-yl)nicotinamide; (44) 6-(Difluoromethyl)-2-((methoxy((2-methyl-2H-tetrazol-5-yl)methyl)amino)methyl)-N-(1-methyl-1H-tetrazol-5-yl)nicotinamide; (45) 2-(((2-ethyl-2H-tetrazol-5-yl)methoxy)methyl)-N-(1-methyl-1H-tetrazol-5-yl)-6-(trifluoromethyl)nicotinamide; (46)N-(1-ethyl-1H-tetrazol-5-yl)-2-(((2-ethyl-2H-tetrazol-5-yl)methoxy)methyl)-6-(trifluoromethyl)nicotinamide; (47) 2-(((2-ethyl-2H-tetrazol-5-yl)methoxy)methyl)-N-(1-n-propyl-1H-tetrazol-5-yl)-6-(trifluoromethyl)nicotinamide; (48)N-(1-allyl-1H-tetrazol-5-yl)-2-(((2-ethyl-2H-tetrazol-5-yl)methoxy)methyl)-6-(trifluoromethyl)nicotinamide; (49) 2-(((2-(methoxymethyl)-2H-tetrazol-5-yl)methoxy)methyl)-N-(1-methyl-1H-tetrazol-5-yl)-6-(trifluoromethyl)nicotinamide; (50) 2-(((2-(difluoromethyl)-2H-tetrazol-5-yl)methoxy)methyl)-N-(1-methyl-1H-tetrazol-5-yl)-6-(trifluoromethyl)nicotinamide; (51) 2-((methyl((2-methyl-2H-tetrazol-5-yl)methyl)amino)methyl)-N-(1-methyl-1H-tetrazol-5-yl)-6-(trifluoromethyl)nicotinamide; (52) 2-((ethyl((2-methyl-2H-tetrazol-5-yl)methyl)amino)methyl)-N-(1-methyl-1H-tetrazol-5-yl)-6-(trifluoromethyl)nicotinamide; (53) 2-((methoxy((2-methyl-2H-tetrazol-5-yl)methyl)amino)methyl)-N-(1-methyl-1H-tetrazol-5-yl)-6-(trifluoromethyl)nicotinamide; (54)N-(1-methyl-1H-tetrazol-5-yl)-2-((((2-methyl-2H-tetrazol-5-yl)methyl)thio)methyl)-6-(trifluoromethyl)nicotinamide; (55)N-(1-methyl-1H-tetrazol-5-yl)-2-((((2-methyl-2H-tetrazol-5-yl)methyl)sulfinyl)methyl)-6-(trifluoromethyl)nicotinamide; (56)N-(1-methyl-1H-tetrazol-5-yl)-2-((((2-methyl-2H-tetrazol-5-yl)methyl)sulfonyl)methyl)-6-(trifluoromethyl)nicotinamide; (57)N-(1-methyl-1H-tetrazol-5-yl)-2-(((2-methyl-2H-tetrazol-5-yl)methoxy)methyl)-6-(trifluoromethyl)pyridine-3-carbothioamide; (58)N-(1-methyl-1H-tetrazol-5-yl)-2-((((2-methyl-2H-tetrazol-5-yl)methyl)thio)methyl)-6-(trifluoromethyl)pyridine-3-carbothioamide; (59) 6-(Difluoromethyl)-N-(1-methyl-1H-tetrazol-5-yl)-2-((((2-methyl-2H-tetrazol-5-yl)methyl)thio)methyl)nicotinamide; (60)N-Benzoyl-N-(1-methyl-1H-tetrazol-5-yl)-2-((((2-methyl-2H-tetrazol-5-yl)methyl)thio)methyl)-6-(trifluoromethyl)nicotinamide; (61)N-(1-methyl-1H-tetrazol-5-yl)-2-((((2-methyl-2H-tetrazol-5-yl)methyl)thio)methyl)-N-(methylsulfonyl)-6-(trifluoromethyl)nicotinamide; (62) 6-(Difluoromethyl)-N-(1-methyl-1H-tetrazol-1-yl)-2-((((2-methyl-2H-tetrazol-5-yl)methyl)sulfinyl)methyl)nicotinamide; (63)N-Benzoyl-6-(difluoromethyl)-N-(1-methyl-1H-tetrazol-5-yl)-2-((((2-methyl-2H-tetrazol-5-yl)methyl)thio)methyl)nicotinamide (Compound No. 2-112); (64) 2-(((1-methyl-1H-1,2,4-triazol-3-yl)methoxy)methyl)-N-(1-methyl-1H-tetrazol-5-yl)-6-(trifluoromethyl)nicotinamide; (65) 2-(((1-methyl-1H-1,2,4-triazol-3-yl)methoxy)methyl)-N-(1-n-propyl-1H-tetrazol-5-yl)-6-(trifluoromethyl)nicotinamide; (66)N-(1-allyl-1H-tetrazol-5-yl)-2-(((1-methyl-1H-1,2,4-triazol-3-yl)methoxy)methyl)-6-(trifluoromethyl)nicotinamide; (67) 2-(((1,5-dimethyl-1H-1,2,4-triazol-3-yl)methoxy)methyl)-N-(1-methyl-1H-tetrazol-5-yl)-6-(trifluoromethyl)nicotinamide; (68) 2-(((1,5-dimethyl-1H-1,2,4-triazol-3-yl)methoxy)methyl)-N-(1-methyl-1H-tetrazol-5-yl)-6-(trifluoromethyl)pyridine-3-carbothioamide; (69)N-(1-methyl-1H-tetrazol-5-yl)-2-(((1-methyl-5-(trifluoromethyl)-1H-1,2,4-triazol-3-yl)methoxy)methyl)-6-(trifluoromethyl)nicotinamide; (70)N-(1-ethyl-1H-tetrazol-5-yl)-2-(((1-methyl-5-(trifluoromethyl)-1H-1,2,4-triazol-3-yl)methoxy)methyl)-6-(trifluoromethyl)nicotinamide; (71) 2-(((1-methyl-5-(trifluoromethyl)-1H-1,2,4-triazol-3-yl)methoxy)methyl)-N-(1-propyl-1H-tetrazol-5-yl)-6-(trifluoromethyl)nicotinamide; (72)N-(1-allyl-1H-tetrazol-5-yl)-2-(((1-methyl-5-(trifluoromethyl)-1H-1,2,4-triazol-3-yl)methoxy)methyl)-6-(trifluoromethyl)nicotinamide; (73) 2-(((1-methyl-5-(trifluoromethyl)-1H-1,2,4-triazol-3-yl)methoxy)methyl)-N-(1-prop-2-yn-1-yl)-1H-tetrazol-5-yl)-6-(trifluoromethyl)nicotinamide; (74) 2-(((5-(difluoromethyl)-1-methyl-1H-1,2,4-triazol-3-yl)methoxy)methyl)-N-(1-methyl-1H-tetrazol-5-yl)-6-(trifluoromethyl)nicotinamide; (75) 2-(((5-(difluoromethyl)-1-methyl-1H-1,2,4-triazol-3-yl)-methoxy)-N-(1-n-propyl-1H-tetrazol-5-yl)-6-(trifluoromethyl)nicotinamide; (76)N-(1-allyl-1H-tetrazol-5-yl)-2-(((5-(difluoromethyl)-1-methyl-1H-1,2,4-triazol-3-yl)methoxy)methyl)-6-(trifluoromethyl)nicotinamide; (77) 2-(((5-(fluoromethyl)-1-methyl-1H-1,2,4-triazol-3-yl)methoxy)methyl)-N-(1-methyl-1H-tetrazol-5-yl)-6-(trifluoromethyl)nicotinamide; (78)N-(1-methyl-1H-tetrazol-5-yl)-2-(((1-methyl-5-vinyl-1H-1,2,4-triazol-3-yl)methoxy)methyl)-6-(trifluoromethyl)nicotinamide; (79)N-(1-methyl-1H-tetrazol-5-yl)-2-(((1-methyl-5-(prop-1-en-2-yl)-1H-1,2,4-triazol-3-yl)methoxy)methyl)-6-(trifluoromethyl)nicotinamide; (80) 2-(((5-methoxy-1-methyl-1H-1,2,4-triazol-3-yl)methoxy)methyl)-N-(1-methyl-1H-tetrazol-5-yl)-6-(trifluoromethyl)nicotinamide; (81)N-(1-methyl-1H-tetrazol-5-yl)-2-(((1-methyl-5-(2,2,2-trifluoroethoxy)-1H-1,2,4-triazol-3-yl)methoxy)methyl)-6-(trifluoromethyl)nicotinamide; (82)N-(1-methyl-1H-tetrazol-5-yl)-2-(((1-methyl-5-(methylthio)-1H-1,2,4-triazol-3-yl)methoxy)methyl)-6-(trifluoromethyl)nicotinamide; (83)N-(1-methyl-1H-tetrazol-5-yl)-2-(((1-methyl-5-(methylsulfonyl)-1H-1,2,4-triazol-3-yl)methoxy)methyl)-6-(trifluoromethyl)nicotinamide; (84) 2-(((5-(dimethylamino)-1-methyl-1H-1,2,4-triazol-3-yl)methoxy)methyl)-N-(1-methyl-1H-tetrazol-5-yl)-6-(trifluoromethyl)nicotinamide; (85) 2-(((5-cyano-1-methyl-1H-1,2,4-triazol-3-yl)methoxy)methyl)-N-(1-methyl-1H-tetrazol-5-yl)-6-(trifluoromethyl)nicotinamide; (86) 2-(((5-chloro-1-methyl-1H-1,2,4-triazol-3-yl)methoxy)methyl)-N-(1-methyl-1H-tetrazol-5-yl)-6-(trifluoromethyl)nicotinamide; (87) 2-(((5-Bromo-1-methyl-1H-1,2,4-triazol-3-yl)methoxy)methyl)-N-(1-methyl-1H-tetrazol-5-yl)-6-(trifluoromethyl)nicotinamide; (88) 2-(((5-Iodo-1-methyl-1H-1,2,4-triazol-3-yl)methoxy)methyl-N-(1-methyl-1H-tetrazol-5-yl)-6-(trifluoromethyl)nicotinamide; (89) Methyl (1-(2-(((1-methyl-1H-1,2,4-triazol-3-yl)methoxy)methyl)-N-(1-methyl-1H-tetrazol-5-yl)-6-(trifluoromethyl)nicotinamido)ethyl)carbonate; (90) Methyl (1-(N-(1-methyl-1H-tetrazol-5-yl)-2-(((2-methyl-2H-tetrazol-5-yl)methoxy)methyl)-6-(trifluoromethyl)pyridine-3-carbothioamido)ethyl)carbonate; (91) Methyl (1-(N-(1-methyl-1H-tetrazol-5-yl)-2-((((2-methyl-2H-tetrazol-5-yl)methyl)thio)methyl)-6-(trifluoromethyl)nicotinamido)ethyl)carbonate; (92) Methyl (1-(N-(1-methyl-1H-tetrazol-5-yl)-2-(((2-methyl-2H-tetrazol-5-yl)methoxy)methyl)-6-(trifluoromethyl)nicotinamido)ethyl)carbonate; (93) Ethyl(1-(N-(1-methyl-1H-tetrazol-5-yl)-2-(((2-methyl-2H-tetrazol-5-yl)methoxy)methyl)-6-(trifluoromethyl)nicotinamido)ethyl)carbonate; (94) Ethyl (1-(N-(1-methyl-1H-tetrazol-5-yl)-2-((((2-methyl-2H-tetrazol-5-yl)methyl)thio)methyl)-6-(trifluoromethyl)pyridine-3-carbothioamido)ethyl)carbonate; (95) Ethyl (1-(4-methyl-5-((2-((((2-methyl-2H-tetrazol-5-yl)methyl)thio)methyl)-6-(trifluoromethyl)nicotinoyl)imino)-4,5-dihydro-1H-tetrazol-1-yl)ethyl)carbonate; (96) Cyclohexyl(1-(N-(1-methyl-1H-tetrazol-5-yl)-2-(((2-methyl-2H-tetrazol-5-yl)methoxy)methyl)-6-(trifluoromethyl)nicotinamido)ethyl)carbonate; (97) isopropyl(1-(N-(1-methyl-1H-tetrazol-5-yl)-2-(((2-methyl-2H-tetrazol-5-yl)methoxy)methyl)-6-(trifluoromethyl)nicotinamido)ethyl)carbonate; and Their pesticide-acceptable salts.

5. A herbicidal composition according to claim 1, wherein the weakening agent is isoxadifen-ethyl.

6. A herbicidal composition in paragraph 1, wherein the weight ratio of the nicotinamide compound or its pesticide-acceptable salt and the laxative is 1:20 to 20:

1.

7. A herbicidal composition in paragraph 6, wherein the weight ratio of the nicotinamide compound or its pesticide-acceptable salt and the laxative is 1:3 to 3:

1.

8. A herbicidal composition according to claim 1, wherein the treatment amount of the nicotinamide compound or its agrochemically feasible salt is 1 to 2000 g ai / ha.

9. A herbicidal composition in claim 8, wherein the treatment amount of the nicotinamide compound or its agrochemically feasible salt is 5 to 500 g ai / ha.

10. A herbicidal composition in which damage to crops caused by the nicotinamide compound represented by the chemical formula 1 or an agrochemically acceptable salt thereof is reduced in the first paragraph.

11. A herbicidal composition according to claim 10, wherein the crop is corn.

12. A herbicidal composition for controlling at least one selected from the group consisting of grass weeds, sedge weeds, and broadleaf weeds in the first paragraph.

13. A method for controlling weeds in a cultivated field, comprising the step of applying an effective amount of a herbicidal composition of any one of claims 1 to 12 to the cultivated field.

14. A method for controlling weeds in a cultivated field, wherein the herbicidal composition is applied after weed emergence; before emergence; or after emergence and before emergence to control weeds.

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