Herbicidal composition

Abstract

The purpose of this invention is to provide a herbicidal composition capable of expanding the herbicidal activity spectrum of a compound represented by formula [1], which is novel and has herbicidal activity, and capable of appropriately controlling monocotyledon and dicotyledon, both of which are important weeds, over a long period of time with a smaller amount of active ingredient.　The herbicidal composition contains (a) the compound represented by formula [1] or a salt thereof, and (b) at least one kind of agricultural / horticultural herbicides.

Description

herbicidal composition

[0001] The present invention relates to a highly effective herbicidal composition and herbicidal method which contain a novel haloalkylsulfonanilide compound and a known herbicide as active ingredients.

[0002] It has been reported that compounds having a haloalkylsulfonylamino group at the 2-position of a benzyl group have herbicidal activity (see, for example, Patent Documents 1 to 18).

[0003] International Publication No. WO 2004 / 011429, International Publication No. WO 2006 / 090792, International Publication No. WO 2008 / 059948, International Publication No. WO 2008 / 102908, International Publication No. WO 2010 / 026989, International Publication No. WO 2010 / 119906, International Publication No. WO 2013 / 083622, International Publication No. WO 2014 / 175206, International Publication No. WO 2015 / 0 No. 04282 International Publication No. 2015 / 097071 International Publication No. 2016 / 056565 International Publication No. 2016 / 207081 International Publication No. 2016 / 207082 International Publication No. 2016 / 207083 JP 2008-074839 JP 2010-209061 JP 2012-180320 JP 2015-020950

[0004]

[0006] Currently, many compounds are in practical use as herbicides, but the effects of existing herbicides on target weeds are not necessarily complete. In view of the current state of weed control, the present invention aims to expand the herbicidal activity spectrum of the compound represented by formula [1], which is a novel compound having herbicidal activity discovered by the present inventors, and to provide a herbicidal composition that can accurately control both important monocotyledonous and dicotyledonous weeds for a long period of time with a smaller amount of active ingredient.

[0005] The present inventors have conducted extensive research into the combined use of the compound of formula [1] with other herbicidally active compounds, and as a result have found that a mixture of the compound of formula [1] with an agricultural or horticultural herbicide exhibits an unexpected and surprising synergistic effect, and that it can control important weeds accurately and for a long period of time with a single treatment at a much smaller amount than the use of each agent alone, and can be used over a wide range of treatment periods from pre-emergence to the growth stage of weeds without harming useful plants, thereby completing the present invention. The present invention encompasses the disclosure of the following herbicidal compositions or methods for controlling plant pests.

[0006] (1) (a) Formula [1] wherein A is an optionally substituted benzene ring or heteroaromatic ring, and E is —C(R ５ ) (R ６ ) -, oxygen atom, sulfur atom, SO, SO ２ , or N(R ７ ), W is an oxygen atom or a sulfur atom, o is 0 to 4, p is 0 to 4, m is 0 to 3, n is 0 to 3, and R １ Halo C １ ~C ６ alkyl, R ２ is a hydrogen atom, Z １ C optionally substituted with one or more substituents selected from １ ~C ６ Alkyl, C ２ ~C ６ Alkenyl, HaloC ２ ~C ６ Alkenyl, C ２ ~C ６ Alkynyl, HaloC ２ ~C ６ Alkynyl, (C １ ~C １２ alkyl) carbonyl, (haloC １ ~C １２ alkyl)carbonyl, (C ３ ~C ６ cycloalkyl)carbonyl, (haloC ３ ~C ６ cycloalkyl)carbonyl, (C １ ~C ６ Alkyl C ３~C ６ cycloalkyl)carbonyl, C １ ~C ６ Alkyl (Halo C ３ ~C ６ cycloalkyl)carbonyl, (C ３ ~C ６ cycloalkoxy)carbonyl, (C ２ ~C ６ alkenyl)carbonyl, (haloC ２ ~C ６ alkenyl)carbonyl, Z ２ Phenyl (C ２ ~C ６ alkenyl)carbonyl, C １ ~C ６ Alkoxy (C ２ ~C ６ alkenyl)carbonyl, (C ２ ~C ６ alkynyl)carbonyl, Z ２ phenylcarbonyl optionally substituted by one or more substituents selected from ２ heterocyclylcarbonyl optionally substituted by one or more substituents selected from ３ ~C ６ Cycloalkyl (C １ ~C ６ alkyl)carbonyl, Z ４ (C １ ~C ６ alkyl) carbonyl, (hydroxy C １ ~C ６ alkyl)carbonyl, C １ ~C ６ Alkoxy (C １ ~C ６ alkyl) carbonyl, haloC １ ~C ６ Alkoxy (C １ ~C ６ alkyl)carbonyl, Z ５ (C １ ~C ６ alkyl) carbonyl, phenoxy (halo C １ ~C６ alkyl)carbonyl, Z ５ substituted by (haloC １ ~C ６ alkyl) carbonyl, tri(C １ ~C ６ alkyl)silyloxy(C １ ~C ６ alkyl)carbonyl, C １ ~C ６ Alkoxy C １ ~C ６ Alkoxy (C １ ~C ６ alkyl)carbonyl, (C １ ~C ６ alkyl) carbonyl (C １ ~C ６ alkyl)carbonyl, (C １ ~C ６ alkyl)carbonyloxy(C １ ~C ６ alkyl)carbonyl, (C １ ~C ６ alkoxy)carbonyl (C １ ~C ６ alkyl)carbonyl, C １ ~C ６ Alkylthio (C １ ~C ６ alkyl) carbonyl, haloC １ ~C ６ Alkylthio (C １ ~C ６ alkyl)carbonyl, (C １ ~C １２ alkoxy)carbonyl, (haloC １ ~C ６ alkoxy)carbonyl, (C ３ ~C ６ cycloalkyloxy)carbonyl, (C ２ ~C ６ alkenyloxy)carbonyl, (haloC ２ ~C ６ alkenyloxy)carbonyl, (C ２ ~C ６ alkynyloxy)carbonyl, Z ２phenoxycarbonyl optionally substituted by one or more substituents selected from ２ heterocyclyloxycarbonyl optionally substituted by one or more substituents selected from ３ ~C ６ Cycloalkyl (C １ ~C ６ alkoxy)carbonyl, Z ４ (C １ ~C ６ alkoxy)carbonyl, (cyano C １ ~C ６ alkoxy)carbonyl, (hydroxy C １ ~C ６ Alkoxy)carbonyl, C １ ~C ６ Alkoxy (C １ ~C ６ Alkoxy)carbonyl, C １ ~C ６ substituted by one or more substituents selected from alkoxy (C １ ~C ６ Alkoxy) carbonyl, halo C １ ~C ６ Alkoxy (C １ ~C ６ Alkoxy) carbonyl, tri C １ ~C ６ Alkylsilyloxy (C １ ~C ６ Alkoxy)carbonyl, C １ ~C ６ Alkoxy C １ ~C ６ Alkoxy (C １ ~C ６ alkoxy)carbonyl, (C １ ~C ６ alkyl)carbonyloxy(C １ ~C ６ Alkoxy)carbonyl, C １ ~C ６ Alkyl sulfonyloxy (C １ ~C ６ alkoxy)carbonyl, (C １ ~C ６ alkyl) carbonyl (C１ ~C ６ alkoxy)carbonyl, (C １ ~C ６ alkoxy)carbonyl (C １ ~C ６ Alkoxy)carbonyl, C １ ~C ６ Alkylthio (C １ ~C ６ Alkoxy) carbonyl, halo C １ ~C ６ Alkylthio (C １ ~C ６ Alkoxy)carbonyl, C １ ~C ６ Alkylsulfinyl (C １ ~C ６ Alkoxy)carbonyl, C １ ~C ６ Alkyl sulfonyl (C １ ~C ６ alkoxy)carbonyl, (C １ ~C ６ alkylthio)carbonyl, (haloC １ ~C ６ alkylthio)carbonyl, mono(C １ ~C ６ alkyl)aminocarbonyl, mono(haloC １ ~C ６ alkyl)aminocarbonyl, di(C １ ~C ６ alkyl)aminocarbonyl, halodi(C １ ~C ６ alkyl)aminocarbonyl, C １ ~C ６ Alkoxyoxalyl, C １ ~C ６ Alkyl sulfonyl, halo C １ ~C ６ Alkylsulfonyl, C ３ ~C ６ Cycloalkylsulfonyl, C ２ ~C ６ Alkenylsulfonyl, HaloC １ ~C ６ Alkenylsulfonyl, Z ２phenylsulfonyl optionally substituted by one or more substituents selected from ２ heterocyclylsulfonyl optionally substituted by one or more substituents selected from ３ ~C ６ Cycloalkyl C １ ~C ６ Alkylsulfonyl, Z ４ C substituted with one substituent selected from １ ~C ６ Alkylsulfonyl, C １ ~C ６ Alkoxy C １ ~C ６ Alkyl sulfonyl, amino sulfonyl, mono C １ ~C ６ alkylaminosulfonyl, di-C which may be the same or different １ ~C ６ Alkylaminosulfonyl, C １ ~C ６ Alkylthio, HaloC １ ~C ６ alkylthio or cyano; Z １ are each independently a halogen atom, C ３ ~C ６ cycloalkyl, Z ２ phenyl optionally substituted by one or more substituents selected from ２ heterocyclyl, cyano, Z ３ C optionally substituted with one or more substituents selected from １ ~C ６ Alkoxy, C ３ ~C ６ cycloalkyloxy, Z ２ phenoxy optionally substituted by one or more substituents selected from ２ phenylcarbonyloxy optionally substituted by one or more substituents selected from ２ heterocyclylcarbonyloxy optionally substituted by one or more substituents selected from the group consisting of １ ~C ６alkyl)carbonyloxy, (C ３ ~C ６ cycloalkyl)carbonyloxy, (C １ ~C ６ alkoxy)carbonyloxy, Z ２ phenoxycarbonyloxy optionally substituted by one or more substituents selected from -CONR １１ R １２ , C optionally substituted by one or more halogen atoms １ ~C ６ alkylthio, C optionally substituted by one or more halogen atoms １ ~C ６ alkylsulfinyl, C optionally substituted by one or more halogen atoms １ ~C ６ Alkylsulfonyl, Z ２ phenylthio optionally substituted by one or more substituents selected from ２ phenylsulfinyl optionally substituted by one or more substituents selected from ４ C optionally substituted with one substituent selected from １ ~C ６ Alkylthio, Z ４ C optionally substituted with one substituent selected from １ ~C ６ Alkylsulfinyl, Z ４ C optionally substituted with one substituent selected from １ ~C ６ alkylsulfinyl, thiocyanato, optionally substituted with one or more halogen atoms (C １ ~C ６ alkyl)carbonyl, optionally substituted with one or more halogen atoms (C １ ~C ６ alkoxy)carbonyl, and Z ２ phenylcarbonyl optionally substituted by one or more substituents selected from ２ are each independently a halogen, C １ ~C ６ Alkyl, C ２ ~C６ Alkenyl, C ２ ~C ６ Alkynyl, C ３ ~C ６ Cycloalkyl, haloC １ ~C ６ Alkyl, haloC ３ ~C ６ Cycloalkyl, C １ ~C ６ Alkoxy, HaloC １ ~C ６ Alkoxy, C １ ~C ６ Alkylthio, HaloC １ ~C ６ Alkylthio, C １ ~C ６ Alkylsulfinyl, HaloC １ ~C ６ Alkylsulfinyl, C １ ~C ６ Alkyl sulfonyl, halo C １ ~C ６ Alkyl sulfonyl, phenyl, (C １ ~C ６ alkyl) carbonyl, (haloC １ ~C ６ alkyl)carbonyl, (C １ ~C ６ alkoxy) carbonyl, carboxyl, mono(C １ ~C ６ alkyl)aminocarbonyl, Z ６ phenyl substituted with one or more substituents selected from the group consisting of ７ heterocyclyl optionally substituted by one or more substituents selected from the following: ７ phenoxy optionally substituted by one or more substituents selected from the group consisting of ７ phenylthio optionally substituted by one or more substituents selected from the following: ７ phenylsulfinyl optionally substituted by one or more substituents selected from the group consisting of ７ phenylsulfonyl optionally substituted by one or more substituents selected from the following: ７ phenylcarbonyl, di(C１ ~C ６ alkyl)aminocarbonyl, —NR １３ R １４ , hydroxyl, cyano, or nitro, or two Z ２ may be joined together with an adjacent carbon atom or nitrogen atom on the benzene ring or heterocycle to form a 5- or 6-membered carbocyclic ring or a 5- or 6-membered heterocyclic ring, wherein the heterocyclic ring is free from oxygen atoms, sulfur atoms, and nitrogen atoms (the nitrogen atoms are C １ ~C ６ Alkyl, C ２ ~C ６ Alkenyl, C ２ ~C ６ Alkynyl, or C ３ ~C ６and wherein the carbocyclic or heterocyclic ring is optionally substituted by one or more halogens; the heteroaromatic ring is thiophene, furan, pyrrole, oxazole, isoxazoline, thiazole, isothiazole, pyrazole, imidazole, 1,3,4-oxadiazole, 1,2,4-oxadiazole, 1,3,4-thiadiazole, 1,2,4-thiadiazole, 1,2,4-triazole, 1,2,3-thiadiazole, 1,2,3-triazole, 1,2,3,4-tetrazole, pyridine, pyrimidine, pyrazine, pyridazine, 1,3,5-triazine, 1,2,4-triazine, benzothiophene, benzofuran, indole, benzothiazole, benzimidazole, benzisoxazole, benzisothiazole, indazole, benzoxazole, quinoline, isoquinoline, quinoxaline, phthalazine, cinnoline, or quinazoline; The heterocyclyl may be thienyl, furyl, pyrrolyl, oxazolyl, isoxazolyl, isoxazolinyl, thiazolyl, isothiazolyl, pyrazolyl, imidazolyl, 1,3,4-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,4-triazolyl, 1,2,3-thiadiazolyl, 1,2,3-triazolyl, 1,2,3,4-tetrazolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, 1,3,5-triazinyl, 1,2,4-triazinyl, benzothienyl, benzofuraf ... Z is aryl, indolyl, benzothiazolyl, benzimidazolyl, benzisoxazolyl, benzisothiazolyl, indazolyl, benzoxazolyl, quinolyl, isoquinolyl, quinoxalinyl, phthalazinyl, cinnolinyl, quinazolinyl, oxiranyl, oxetanyl, tetrahydrofuranyl, tetrahydrothienyl, 1,1-dioxytetrahydrothienyl, tetrahydropyranyl, tetrahydrothiopyranyl, 1,3-dioxanyl, 2-oxo-1,3-dioxolanyl, 2-oxo-1,3-dioxolyl, or 2,5-dioxopyrrolidinyl; ３ is a halogen atom, Z ２Phenyl, triC optionally substituted by one or more substituents selected from １ ~C ６ Alkylsilyl, C １ ~C ６ alkyldiphenylsilyl, C optionally substituted with one or more halogen atoms １ ~C ６ Alkoxy, Z ２ phenylcarbonyloxy optionally substituted by one or more substituents selected from ２ phenylsulfonyl optionally substituted by one or more substituents selected from ４ Is Z ２ phenyl optionally substituted by one or more substituents selected from ２ and Z is a heterocyclyl optionally substituted by one or more substituents selected from ５ Is Z ２ phenoxy optionally substituted by one or more substituents selected from ６ Is Ji (C １ ~C ６ Z is selected from the group consisting of alkyl)aminocarbonyl, hydroxy, amino, cyano, and nitro; ７ is a halogen, C １ ~C ６ Alkyl, C ２ ~C ６ Alkenyl, C ２ ~C ６ Alkynyl, C ３ ~C ６ Cycloalkyl, haloC １ ~C ６ Alkyl, haloC ３ ~C ６ Cycloalkyl, C １ ~C ６ Alkoxy, HaloC １ ~C ６ Alkoxy, C １ ~C ６ Alkylthio, HaloC １ ~C ６ Alkylthio, C １ ~C ６ Alkylsulfinyl, HaloC １~C ６ Alkylsulfinyl, C １ ~C ６ Alkyl sulfonyl, halo C １ ~C ６ Alkylsulfonyl, (C １ ~C ６ alkyl) carbonyl, (haloC １ ~C ６ alkyl)carbonyl, (C １ ~C ６ alkoxy) carbonyl, carboxyl, mono(C １ ~C ６ alkyl)aminocarbonyl, di(C １ ~C ６ is selected from the group consisting of alkyl)aminocarbonyl, hydroxyl, amino, cyano, and nitro; ８ Is Z ２ phenylthio optionally substituted by one or more substituents selected from ２ and Z ２ phenylsulfonyl optionally substituted by one or more substituents selected from １１ and R １２ are each independently a hydrogen atom, C １ ~C ６ Alkyl, and Z ２ phenyl, optionally substituted with one or more substituents selected from １３ is a hydrogen atom or C １ ~C ６ alkyl; R １４ is a hydrogen atom, or Z ７ phenyl optionally substituted by one or more substituents selected from ３ and R ４ are each independently a hydrogen atom, C １ ~C ６ Alkyl, haloC １ ~C ６ Alkyl, C １ ~C ６ Cycloalkyl, haloC１ ~C ６ Cycloalkyl, C １ ~C ６ Alkoxy, HaloC １ ~C ６ alkoxy, halogen, or cyano, or R ３ and R ４ can be bonded to each other to form a 3- to 7-membered ring, R ５ and R ６ are each independently a hydrogen atom, a halogen atom, or C １ ~C ６ Alkyl, haloC １ ~C ６ Alkyl, C ２ ~C ６ Alkenyl, C ２ ~C ６ Alkynyl, C ３ ~C ６ Cycloalkyl, haloC ３ ~C ６ Cycloalkyl, hydroxy C １ ~C ６ Alkyl, C １ ~C ６ Alkoxy C １ ~C ６ Alkyl, haloC １ ~C ６ Alkoxy C １ ~C ６ Alkyl, C １ ~C ６ Alkylthio C １ ~C ６ Alkyl, haloC １ ~C ６ Alkylthio C １ ~C ６ Alkyl, mono(C １ ~C ６ Alkyl)amino C １ ~C ６ alkyl, di-(C １ ~C ６ Alkyl)amino C １ ~C ６ Alkyl, Z ２ phenyl optionally substituted by one or more substituents selected from ２heterocyclyl optionally substituted by one or more substituents selected from ４ C substituted with one substituent selected from １ ~C ６ Alkyl, Z ５ C substituted with one substituent selected from １ ~C ６ Alkyl, (C １ ~C ６ alkyl) carbonyl, (haloC １ ~C ６ alkyl)carbonyl, Z ２ phenylcarbonyl optionally substituted by one or more substituents selected from (C １ ~C ６ alkoxy)carbonyl, (haloC １ ~C ６ alkoxy)carbonyl, carboxyl, -NR １１ R １２ , C １ ~C ６ Alkoxy, HaloC １ ~C ６ Alkoxy, Z ２ phenoxy optionally substituted by one or more substituents selected from C １ ~C ６ Alkylthio, HaloC １ ~C ６ Alkylthio, Z ２ phenylthio optionally substituted by one or more substituents selected from C １ ~C ６ Alkyl sulfonyl, halo C １ ~C ６ Alkylsulfonyl, mono(C １ ~C ６ alkyl)amino, di(C １ ~C ６ alkyl)amino, (C １ ~C ６ alkyl)carbonyloxy, hydroxyl, amino, cyano, or nitro, or R on the same carbon ５ and R ６ are bonded to each other to form an oxygen atom, a sulfur atom, and a nitrogen atom (the nitrogen atom is C １ ~C ６Alkyl, C ２ ~C ６ Alkenyl, C ２ ~C ６ Alkynyl, or C ３ ~C ６ or R ５ and R ６ are R on different carbons ５ or R ６ and bonded to an oxygen atom, a sulfur atom, and a nitrogen atom (the nitrogen atom is C １ ~C ６ Alkyl, C ２ ~C ６ Alkenyl, C ２ ~C ６ Alkynyl, or C ３ ~C ６ and optionally substituted C, which may be interrupted by 1 or 2 heteroatoms selected from the group consisting of: １ ~C ４ Alkylene, HaloC １ ~C ４ Alkylene, C ２ ~C ４ Alkenylene or halo C ２ ~C ４ The alkenylene can form a 3- to 8-membered ring, or R ５ and R ６ is R on the adjacent carbon ５ or R ６ can form a bond together with R ７ is a hydrogen atom, C １ ~C ６ Alkyl, haloC １ ~C ６ Alkyl, C ３ ~C ６ Cycloalkyl, haloC ３ ~C ６ Cycloalkyl, C ２ ~C ６ Alkenyl, HaloC ２~C ６ Alkenyl, C ２ ~C ６ Alkynyl, hydroxy C １ ~C ６ Alkyl, C １ ~C ６ Alkoxy C １ ~C ６ Alkyl, haloC １ ~C ６ Alkoxy C １ ~C ６ Alkyl, C ３ ~C ６ Cycloalkyl C １ ~C ６ Alkyl, Z ４ C substituted with one substituent selected from １ ~C ６ Alkyl, Z ２ phenyl optionally substituted by one or more substituents selected from ４ C substituted with one substituent selected from １ ~C ６ Alkyl, (C １ ~C ６ Alkyl)carbonyl C １ ~C ６ Alkyl, (haloC １ ~C ６ Alkyl)carbonyl C １ ~C ６ Alkyl, (C １ ~C ６ Alkoxy)carbonyl C １ ~C ６ Alkyl, (haloC １ ~C ６ Alkoxy)carbonyl C １ ~C ６ Alkyl, (C １ ~C ６ alkyl) carbonyl, (haloC １ ~C ６ alkyl)carbonyl, (C ３ ~C ６ cycloalkyl)carbonyl, C ３ ~C ６ Cycloalkyl (C １ ~C ６ alkyl)carbonyl, (C２ ~C ６ alkenyl)carbonyl, Z ２ phenylcarbonyl optionally substituted by one or more substituents selected from ２ heterocyclylcarbonyl optionally substituted by one or more substituents selected from (C １ ~C ６ alkoxy)carbonyl, (haloC １ ~C ６ alkoxy)carbonyl, Z ２ phenoxycarbonyl, aminocarbonyl, mono(C １ ~C ６ alkyl) aminocarbonyl, monohalo (C １ ~C ６ alkyl)aminocarbonyl, di(C １ ~C ６ alkyl)aminocarbonyl, halodi(C １ ~C ６ alkyl)aminocarbonyl, (C １ ~C ６ alkylthio)carbonyl, (haloC １ ~C ６ alkylthio)carbonyl, C １ ~C ６ Alkyl sulfonyl, halo C １ ~C ６ Alkylsulfonyl, Z ２ Phenylsulfonyl optionally substituted by one or more substituents selected from C １ ~C ６ Alkylthio C １ ~C ６ Alkyl, haloC １ ~C ６ Alkylthio C １ ~C ６ Alkyl, Z ８ C substituted with one substituent selected from １ ~C ６ Alkyl, C １ ~C ６ Alkylsulfinyl C １ ~C ６Alkyl, haloC １ ~C ６ Alkylsulfinyl C １ ~C ６ Alkyl, C １ ~C ６ Alkylsulfonyl C １ ~C ６ Alkyl, haloC １ ~C ６ Alkylsulfonyl C １ ~C ６ alkyl, cyano, amino, or hydroxy; X is independently a hydrogen atom, a halogen atom, C １ ~C ６ Alkyl, C ２ ~C ６ Alkenyl, C ２ ~C ６ Alkynyl, C ３ ~C ６ Cycloalkyl, haloC １ ~C ６ Alkyl, haloC ２ ~C ６ Alkenyl, HaloC ２ ~C ６ Alkynyl, HaloC ３ ~C ６ Cycloalkyl, C １ ~C ６ Alkoxy, HaloC １ ~C ６ Alkoxy, C ２ ~C ６ Alkenyloxy, C ２ ~C ６ Alkynyloxy, C ３ ~C ６ Cycloalkyl C １ ~C ６ Alkyloxy, Phenyl C １ ~C ６ Alkyloxy, (C １ ~C ６ alkyl)carbonyloxy, Z ２ phenylcarbonyloxy optionally substituted by one or more substituents selected from ２ heterocyclylcarbonyloxy optionally substituted by one or more substituents selected from (C １ ~C６ alkoxy)carbonyloxy, (C １ ~C ６ alkylthio)carbonyloxy, C １ ~C ６ Alkyl sulfonyloxy, halo C １ ~C ６ Alkyl sulfonyloxy, phenyl sulfonyloxy, diC １ ~C ６ Alkylphosphorooxy, Tri C １ ~C ６ Alkylsilyloxy, C １ ~C ６ Alkoxy C １ ~C ６ Alkyl, C １ ~C ６ Alkylthio, HaloC １ ~C ６ Alkylthio, C １ ~C ６ Alkylsulfinyl, HaloC １ ~C ６ Alkylsulfinyl, C １ ~C ６ Alkyl sulfonyl, halo C １ ~C ６ Alkylsulfonyl, Z ２ phenyl optionally substituted by one or more substituents selected from ２ heterocyclyl optionally substituted by one or more substituents selected from ２ phenoxy optionally substituted by one or more substituents selected from ２ phenylthio optionally substituted by one or more substituents selected from ２ phenylsulfinyl optionally substituted by one or more substituents selected from ２ phenylsulfonyl, di(C １ ~C ６ alkyl)amino, (C １ ~C ６ alkyl)carbonylamino, bis((C １ ~C ６ Alkyl) carbonyl) amino, halo C １~C ６ Alkyl sulfonylamino, morpholinyl, isoindoline-1,3-dione-2-yl, (C １ ~C ６ alkyl) carbonyl, (haloC １ ~C ６ alkyl)carbonyl, Z ２ phenylcarbonyl optionally substituted by one or more substituents selected from (C １ ~C ６ alkoxy) carbonyl, carboxyl, mono(C １ ~C ６ alkyl)aminocarbonyl, di(C １ ~C ６ alkyl)aminocarbonyl, Z ２ phenylaminocarbonyl, phenyl (C １ ~C ６ alkylamino)carbonyl, Z ４ (C １ ~C ６ or two Xs connected to adjacent carbon or nitrogen atoms on a benzene ring or heterocycle together with the ring atoms to which they are attached form a 4- to 6-membered carbocyclic or heterocyclic ring, the heterocyclic ring containing one or two heteroatoms selected from the group consisting of oxygen, sulfur, and nitrogen atoms, the nitrogen atom being C １ ~C ６ Alkyl, C ２ ~C ６ Alkenyl, C ２ ~C ６ Alkynyl, or C ３ ~C ６ Y is independently a hydrogen atom, a halogen atom, a C １ ~C ６ Alkyl, C ２ ~C ６ Alkenyl, C ２ ~C ６ Alkynyl, C ３ ~C ６Cycloalkyl, haloC １ ~C ６ Alkyl, haloC ２ ~C ６ Alkenyl, HaloC ２ ~C ６ Alkynyl, HaloC ３ ~C ６ Cycloalkyl, C １ ~C ６ Alkoxy, HaloC １ ~C ６ Alkoxy, C ２ ~C ６ Alkenyloxy, C ２ ~C ６ Alkynyloxy, C ３ ~C ６ Cycloalkyl C １ ~C ６ Alkyloxy, Phenyl C １ ~C ６ Alkyloxy, (C １ ~C ６ alkyl)carbonyloxy, Z ２ phenylcarbonyloxy optionally substituted by one or more substituents selected from ２ heterocyclylcarbonyloxy optionally substituted by one or more substituents selected from (C １ ~C ６ alkoxy)carbonyloxy, (C １ ~C ６ alkylthio)carbonyloxy, C １ ~C ６ Alkyl sulfonyloxy, halo C １ ~C ６ Alkyl sulfonyloxy, phenyl sulfonyloxy, diC １ ~C ６ Alkylphosphorooxy, Tri C １ ~C ６ Alkylsilyloxy, C １ ~C ６ Alkoxy C １ ~C ６ Alkyl, C １ ~C ６ Alkylthio, HaloC １ ~C ６ Alkylthio, C１ ~C ６ Alkylsulfinyl, HaloC １ ~C ６ Alkylsulfinyl, C １ ~C ６ Alkyl sulfonyl, halo C １ ~C ６ Alkylsulfonyl, Z ２ phenyl optionally substituted by one or more substituents selected from ２ heterocyclyl optionally substituted by one or more substituents selected from ２ phenoxy optionally substituted by one or more substituents selected from ２ phenylthio optionally substituted by one or more substituents selected from ２ phenylsulfinyl optionally substituted by one or more substituents selected from ２ phenylsulfonyl, di(C １ ~C ６ alkyl)amino, (C １ ~C ６ alkyl)carbonylamino, bis((C １ ~C ６ Alkyl) carbonyl) amino, halo C １ ~C ６ Alkyl sulfonylamino, morpholinyl, isoindoline-1,3-dione-2-yl, (C １ ~C ６ alkyl) carbonyl, (haloC １ ~C ６ alkyl)carbonyl, Z ２ phenylcarbonyl optionally substituted by one or more substituents selected from (C １ ~C ６ alkoxy)carbonyl, carboxyl, -NR １１ R １２ , hydroxy, amino, cyano, or nitro; or two Y's together with adjacent carbon or nitrogen atoms on the benzene ring may form a 5- or 6-membered carbocyclic or 5- or 6-membered heterocyclic ring, wherein the heterocyclic ring is composed of oxygen, sulfur, and nitrogen atoms (the nitrogen atoms being C１ ~C ６ Alkyl, C ２ ~C ６ Alkenyl, C ２ ~C ６ Alkynyl, or C ３ ~C ６ a compound represented by the formula (I) or a salt thereof, which contains one or two heteroatoms selected from the group consisting of a carbocyclic ring or a heterocyclic ring, each of which may be substituted with one or more halogen atoms; and (b) at least one agricultural or horticultural herbicide.

[0007] (2) (a') Formula [1a] {wherein E is —CH ２ -, W is an oxygen atom or a sulfur atom, m is 0, n is 0, 1 or 3, R １ Fluoro-C １ ~C ６ alkyl, R ２ is a hydrogen atom, C １ ~C ６ Alkoxy C １ ~C ６ alkyl, or (C １ ~C １２ alkoxy)carbonyl, R ３ and R ４ is a hydrogen atom, and X １ , X ２ , X ３ and X ４ are independently a hydrogen atom, a halogen atom, or C １ ~C ６ Alkyl, haloC １ ~C ６ Alkyl, C １ ~C ６ Alkoxy, C ２ ~C ６ Alkenyloxy, C ２ ~C ６ Alkynyloxy, C ３ ~C ６ Cycloalkyl C １ ~C ６ Alkyloxy, Phenyl C １ ~C ６ Alkyloxy, (C１ ~C ６ alkyl)carbonyloxy, Z ２ phenylcarbonyloxy, heterocyclylcarbonyloxy, (C １ ~C ６ alkoxy)carbonyloxy, (C １ ~C ６ alkylthio)carbonyloxy, C １ ~C ６ Alkyl sulfonyloxy, halo C １ ~C ６ Alkyl sulfonyloxy, phenyl sulfonyloxy, diC １ ~C ６ Alkylphosphorooxy, Tri C １ ~C ６ Alkylsilyloxy, C １ ~C ６ Alkoxy C １ ~C ６ alkyl, phenyl, hydroxyl, amino, cyano, or nitro; Y １ , Y ２ , Y ３ and Y ４ are each independently a hydrogen atom or a haloC １ ~C ６ alkyl, and Z ２ is nitro} or a salt thereof; and (b) at least one agricultural and horticultural herbicide.

[0008] (3) (a'') Formula [1a] {wherein E is —CH ２ -, W is an oxygen atom or a sulfur atom, m is 0, n is 2, and R １ Fluoro-C １ ~C ６ alkyl, R ２ is a hydrogen atom, C ２ ~C ６ Alkynyl, Z ４ C substituted with one substituent selected from １ ~C ６ Alkyl, cyano C １ ~C６ Alkyl, C １ ~C ６ Alkoxy C １ ~C ６ Alkyl, (C １ ~C ６ Alkoxy)carbonyloxy C １ ~C ６ Alkyl, (C １ ~C １２ alkyl) carbonyl, (haloC １ ~C １２ alkyl)carbonyl, (C ３ ~C ６ cycloalkyl)carbonyl, C １ ~C ６ Alkyl (C ３ ~C ６ cycloalkyl)carbonyl, C １ ~C ６ Alkyl halo (C ３ ~C ６ cycloalkyl)carbonyl, (C ２ ~C ６ alkenyl)carbonyl, C １ ~C ６ Alkoxy (C ２ ~C ６ alkenyl)carbonyl, phenylcarbonyl, Z ２ heterocyclylcarbonyl optionally substituted by one or more substituents selected from ３ ~C ６ Cycloalkyl (C １ ~C ６ alkyl) carbonyl, hydroxy (C １ ~C ６ alkyl)carbonyl, C １ ~C ６ Alkoxy (C １ ~C ６ alkyl) carbonyl, tri(C １ ~C ６ alkyl)silyloxy(C １ ~C ６ alkyl)carbonyl, (C １ ~C ６ alkyl)carbonyloxy(C １ ~C ６ alkyl)carbonyl, C１ ~C ６ Alkylthio (C １ ~C ６ alkyl)carbonyl, (C １ ~C １２ alkoxy)carbonyl, (haloC １ ~C ６ alkoxy)carbonyl, (C ３ ~C ６ cycloalkyloxy)carbonyl, (C ２ ~C ６ alkenyloxy)carbonyl, (C ２ ~C ６ alkynyloxy)carbonyl, Z ２ phenoxycarbonyl optionally substituted by one or more substituents selected from ２ heterocyclyloxycarbonyl optionally substituted by one or more substituents selected from ３ ~C ６ Cycloalkyl (C １ ~C ６ alkoxy)carbonyl, Z ４ (C １ ~C ６ alkoxy)carbonyl, (cyano C １ ~C ６ alkoxy)carbonyl, (hydroxy C １ ~C ６ Alkoxy)carbonyl, C １ ~C ６ Alkoxy (C １ ~C ６ Alkoxy)carbonyl, C １ ~C ６ substituted by one or more substituents selected from alkoxy (C １ ~C ６ alkoxy)carbonyl, (C １ ~C ６ alkyl)diphenylsilyloxy(C １ ~C ６ alkoxy)carbonyl, (C １ ~C ６ alkyl)carbonyloxy(C １ ~C ６ Alkoxy)carbonyl, C１ ~C ６ Alkyl sulfonyloxy (C １ ~C ６ alkoxy)carbonyl, (C １ ~C ６ alkyl) carbonyl (C １ ~C ６ alkoxy)carbonyl, (C １ ~C ６ alkoxy)carbonyl (C １ ~C ６ Alkoxy)carbonyl, C １ ~C ６ Alkylthio (C １ ~C ６ Alkoxy)carbonyl, C １ ~C ６ Alkyl sulfonyl (C １ ~C ６ alkoxy)carbonyl, (C １ ~C ６ alkylthio)carbonyl, mono(C １ ~C ６ alkyl)aminocarbonyl, di(C １ ~C ６ alkyl)aminocarbonyl, C １ ~C ６ Alkyl sulfonyl, halo C １ ~C ６ Alkylsulfonyl, or C ３ ~C ６ cycloalkylsulfonyl, R ３ and R ４ is a hydrogen atom, and X １ , X ２ , X ３ and X ４ are independently a hydrogen atom, a halogen atom, or C １ ~C ６ Alkyl, C ３ ~C ６ Cycloalkyl, haloC １ ~C ６ Alkyl, C １ ~C ６ Alkoxy, HaloC １ ~C ６ Alkoxy, C ２ ~C ６Alkynyloxy, (C １ ~C ６ alkyl)carbonyloxy, phenylcarbonyloxy, (C １ ~C ６ alkoxy)carbonyloxy, C １ ~C ６ Alkyl sulfonyloxy, halo C １ ~C ６ Alkylsulfonyloxy, C １ ~C ６ Alkylthio, C １ ~C ６ alkylsulfonyl, phenyl, di(C １ ~C ６ alkyl)amino, (C １ ~C ６ alkyl)carbonylamino, bis((C １ ~C ６ Alkyl) carbonyl) amino, halo C １ ~C ６ Alkyl sulfonylamino, morpholinyl, isoindoline-1,3-dione-2-yl, (C １ ~C ６ alkoxy)carbonyl, hydroxyl, cyano, or nitro, or X １ and X ２ , X ２ and X ３ , and X ３ and X ４ may be taken together with the carbon atoms to which they are attached to form a 5- or 6-membered carbocyclic ring or a 5- or 6-membered heterocyclic ring, wherein the heterocyclic ring contains 1 or 2 heteroatoms selected from sulfur atoms and nitrogen atoms; Y １ , Y ２ , Y ３ and Y ４ are independently a hydrogen atom, a halogen atom, or C １ ~C ６ Alkyl, haloC １ ~C ６ Alkyl, C １ ~C ６ alkoxy or hydroxyl group, or Y １ and Y ２ , Y ２ and Y ３ , and Y３ and Y ４ may form a 4- to 6-membered carbocyclic ring together with the carbon atom to which they are attached, ２ is C １ ~C ６ Alkyl, C １ ~C ６ alkoxy, or nitro, and the heterocyclyl is thienyl, furyl, pyrrolyl, oxiranyl, oxetanyl, tetrahydrofuranyl, tetrahydrothienyl, 1,1-dioxytetrahydrothienyl, tetrahydropyranyl, tetrahydrothiopyranyl, 1,3-dioxanyl, 2-oxo-1,3-dioxolanyl, 2-oxo-1,3-dioxolyl, or 2,5-dioxopyrrolidinyl} or a salt thereof; and (b) at least one agricultural and horticultural herbicide.

[0009] (4) In the formula [1a], n is 2, and R １ is trifluoromethyl, R ２ is a hydrogen atom, (C ３ ~C ６ cycloalkyl)carbonyl, (C ２ ~C ４ alkenyl)carbonyl, C １ ~C ６ Alkoxy (C １ ~C ６ alkyl)carbonyl, 2-furylcarbonyl, C １ ~C ６ Alkylthio (C １ ~C ６ alkyl)carbonyl, (C １ ~C ５ alkoxy)carbonyl, (haloC １ ~C ３ alkoxy)carbonyl, (C ３ ~C ４ cycloalkyloxy)carbonyl, (C ２ ~C ３ alkynyloxy)carbonyl, heterocyclyloxycarbonyl, C ３ ~C ４ Cycloalkyl (C １ ~C ２alkoxy) carbonyl, heterocyclyl (C １ ~C ２ alkoxy)carbonyl, (cyano C １ ~C ６ alkoxy)carbonyl, (hydroxy C １ ~C ６ Alkoxy)carbonyl, C １ ~C ６ Alkoxy (C １ ~C ６ Alkoxy)carbonyl, C １ ~C ２ alkylsulfonyl, or (C １ ~C ４ alkylthio)carbonyl, １ is a fluorine atom, a chlorine atom, or methyl; X ２ and X ３ is a hydrogen atom, and X ４ is a hydrogen atom, a fluorine atom, a chlorine atom, methyl, trifluoromethyl, or methoxy; １ , Y ２ , Y ３ and Y ４ is a hydrogen atom, and the heterocyclyl is oxiranyl, oxetanyl, tetrahydrofuranyl, or tetrahydropyranyl. The herbicidal composition according to (3).

[0010] (5) Formula [1b] {wherein Het is E is selected from ２ -, W is an oxygen atom, m is 0, n is 1 to 2, and R １ Fluoro-C １ ~C ６ alkyl, R ２ is a hydrogen atom or (C １ ~C １２ alkoxy)carbonyl, R ３ and R ４ is a hydrogen atom, and Y １ , Y ２ , Y ３ and Y ４is a hydrogen atom} or a salt thereof; and (b) at least one agricultural and horticultural herbicide.

[0011] (6) In the formula [1b], Het is Het-1 or Het-2, n is 2, and R １ is trifluoromethyl, R ２ is a hydrogen atom or (C ２ ~C ６ The herbicidal composition according to (5), wherein the aryl group is a hydroxyl group (alkoxy)carbonyl.

[0012] (7) The compound represented by the formula [1] or a salt thereof is N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-azabicyclo[4.2.0]octa-1(6),2,4-trien-8-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5-fluoro-7-azabicyclo[4.2.0]octa-1(6),2,4-trien-8-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-4-fluoro-7-azabicyclo[4.2.0]octa-1(6),2,4-trien-8-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-3-fluoro-7-azabicyclo[4.2.0]octa-1(6),2,4-trien-8-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-2-fluoro-7-azabicyclo[4.2.0]octa-1(6),2,4-trien-8-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-2-trifluoromethyl-7-azabicyclo[4.2.0]octa-1(6),2,4-trien-8-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-2,5-dichloro-7-azabicyclo[4.2.0]octa-1(6),2,4-trien-8-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-3,4-difluoro-7-azabicyclo[4.2.0]octa-1(6),2,4-trien-8-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-5-fluoro-7-azabicyclo[4.2.0]octa-1(6),2,4-trien-8-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-4-fluoro-7-azabicyclo[4.2.0]octa-1(6),2,4-trien-8-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-3-fluoro-7-azabicyclo[4.2.0]octa-1(6),2,4-trien-8-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-1,3-dihydroisoindol-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-fluoro-1,3-dihydroisoindol-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-chloro-1,3-dihydroisoindol-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-bromo-1,3-dihydroisoindol-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-methyl-1,3-dihydroisoindol-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-phenyl-1,3-dihydroisoindol-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-cyano-1,3-dihydroisoindol-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-hydroxy-1,3-dihydroisoindol-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-methoxy-1,3-dihydroisoindol-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-acetoxy-1,3-dihydroisoindol-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-benzoyloxy-1,3-dihydroisoindol-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-(4-nitrobenzoyl)oxy-1,3-dihydroisoindol-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-methoxycarbonyloxy-1,3-dihydroisoindol-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-(2-propylthio)carbonyloxy-1,3-dihydroisoindol-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-(1H-imidazol-1-yl-carbonyloxy)-1,3-dihydroisoindol-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-(pyrrolidin-1-yl-carbonyloxy)-1,3-dihydroisoindol-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-methanesulfonyloxy-1,3-dihydroisoindol-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-trifluoromethanesulfonyloxy-1,3-dihydroisoindol-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-phenylsulfonyloxy-1,3-dihydroisoindol-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-diethylphosphorooxy-1,3-dihydroisoindol-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-tert-butyldimethylsilyloxy-1,3-dihydroisoindol-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-propargyloxy-1,3-dihydroisoindol-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-allyloxy-1,3-dihydroisoindol-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-benzyloxy-1,3-dihydroisoindol-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-cyclopropylmethyloxy-1,3-dihydroisoindol-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-amino-1,3-dihydroisoindol-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-acetylamino-1,3-dihydroisoindol-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-bisacetylamino-1,3-dihydroisoindol-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-trifluoromethanesulfonylamino-1,3-dihydroisoindol-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-(isoindoline-1,3-dione-2-yl)-1,3-dihydroisoindol-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-6-fluoro-1,3-dihydroisoindol-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-6-methyl-1,3-dihydroisoindol-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-6-hydroxy-1,3-dihydroisoindol-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-6-methoxy-1,3-dihydroisoindol-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-6-acetoxy-1,3-dihydroisoindol-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-6-trifluoromethanesulfonyloxy-1,3-dihydroisoindol-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-6-propargyloxy-1,3-dihydroisoindol-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-6-nitro-1,3-dihydroisoindol-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-6-(isoindoline-1,3-dione-2-yl)-1,3-dihydroisoindol-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5-bromo-1,3-dihydroisoindol-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5-methyl-1,3-dihydroisoindol-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5-hydroxy-1,3-dihydroisoindol-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5-methoxy-1,3-dihydroisoindol-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5-acetoxy-1,3-dihydroisoindol-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5-propargyloxy-1,3-dihydroisoindol-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-4-hydroxy-1,3-dihydroisoindol-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-4-methoxy-1,3-dihydroisoindol-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-4-acetoxy-1,3-dihydroisoindol-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-4-trifluoromethanesulfonyloxy-1,3-dihydroisoindol-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-4-propargyloxy-1,3-dihydroisoindol-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-4-nitro-1,3-dihydroisoindol-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5-fluoro-6-nitro-1,3-dihydroisoindol-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5,6-dibromo-4-methoxy-1,3-dihydroisoindol-1-one, N-[2-(N-trifluoromethanesulfonyl)amino-5-trifluoromethyl-benzyl]-1,3-dihydroisoindol-1-one, N-[2-(N-trifluoromethanesulfonyl)amino-5-trifluoromethyl-benzyl]-5-bromo-1,3-dihydroisoindol-1-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-1,3-dihydroisoindol-1-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-7-amino-1,3-dihydroisoindol-1-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-5-bromo-1,3-dihydroisoindol-1-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)amino-5-trifluoromethyl-benzyl]-1,3-dihydroisoindol-1-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)amino-5-trifluoromethyl-benzyl]-5-bromo-1,3-dihydroisoindol-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-methoxymethyloxy-1,3-dihydroisoindol-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-8-fluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-8-chloro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-8-bromo-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-8-iodo-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-8-methyl-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-8-cyclopropyl-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-8-phenyl-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-8-trifluoromethyl-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-8-cyano-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-8-hydroxy-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-8-methoxy-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-8-acetoxy-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-8-difluoromethoxy-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-8-trifluoromethoxy-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-8-propargyloxy-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-8-dimethylamino-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-8-methoxycarbonyl-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-fluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-chloro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-bromo-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-iodo-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-methyl-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-ethyl-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-tert-butyl-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-phenyl-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-trifluoromethyl-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-nitro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-hydroxy-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-methoxy-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-ethoxycarbonyloxy-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-benzoyloxy-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-propargyloxy-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-trifluoromethoxy-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-6-fluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-6-chloro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-6-bromo-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-6-iodo-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-6-methyl-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-6-trifluoromethyl-3,4-dihydroisoquinolin-1(2H)-one4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-6-methoxy-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5-fluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5-chloro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5-methyl-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5-nitro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5-methoxy-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5-acetoxy-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5-methanesulfonyloxy-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5-trifluoromethoxy-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5-ethoxycarbonyloxy-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5-benzoyloxy-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5-propargyloxy-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-8-fluoro-7-methyl-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-8-fluoro-7-nitro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7,8-dichloro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-8-chloro-7-methyl-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-6,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-8-fluoro-6-methyl-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-6-cyclopropyl-8-fluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-6-cyano-8-fluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-6,8-dichloro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-6,8-dimethyl-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5-chloro-8-fluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5-bromo-8-fluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-8-fluoro-5-methyl-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-8-fluoro-5-trifluoromethyl-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-8-fluoro-5-methoxy-3,4-dihydroisoquinolin-1(2H)-one4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5-chloro-8-fluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5,8-dichloro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5-fluoro-8-hydroxy-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5-fluoro-8-methoxy-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5-fluoro-8-methanesulfonyloxy-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5-fluoro-8-dimethylamino-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5-fluoro-8-(N-morpholinyl)-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5-fluoro-8-methylthio-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5-fluoro-8-methanesulfonyl-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5,8-bis(methanesulfonyl)-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-6,7-dichloro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-6-fluoro-7-methyl-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-6-chloro-7-methyl-3,4-dihydroisoquinolin-1(2H)-one4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-6-fluoro-7-nitro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-6-chloro-7-nitro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5,6-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-6,8-difluoro-7-nitro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-6,8-dichloro-7-nitro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-3,4-dihydrobenzo[h]isoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-3,4-dihydrobenzo[g]isoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7,8-dihydrothiazolo[4,5-h]isoquinolin-9(6H)-one, N-[2-(N-methyl-N-trifluoromethanesulfonyl)aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-propargyl-N-trifluoromethanesulfonyl)aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-(4-methoxybenzyl)-N-trifluoromethanesulfonyl)aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-[3-(1,3-dioxan-2-yl)propanyl]-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-cyanomethyl-N-trifluoromethanesulfonyl)aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one4-dihydroisoquinolin-1(2H)-one, N-[2-(N-ethoxymethyl-N-trifluoromethanesulfonyl)aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(isopropyloxycarbonyloxymethyl)-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-acetyl-N-trifluoromethanesulfonyl)aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-ethylcarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(1-propylcarbonyl)-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(2-propylcarbonyl)-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(2-methyl-1-propylcarbonyl)-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(2,2-dimethyl-1-propylcarbonyl)-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-chloromethylcarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-cyclopropylcarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-8-fluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-cyclopropylcarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-8-chloro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-cyclopropylcarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-6-chloro-3,4-dihydroisoquinolin-1(2H)-one4-dihydroisoquinolin-1(2H)-one, N-[2-(N-cyclopropylcarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-cyclopropylcarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-8-fluoro-5-methyl-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(2-methyl-cyclopropyl)carbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(2,2-dimethyl-cyclopropyl)carbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(2,2-dichloro-1-methyl-cyclopropyl)carbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-cyclobutylcarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-cyclopentylcarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-cyclohexylcarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-acryloyl-N-trifluoromethanesulfonyl)aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(prop-1-en-1-yl)carbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(2-methyl-prop-1-en-1-yl)carbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(prop-1-en-2-yl)carbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(3-ethoxyacryloyl)-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-benzoyl-N-trifluoromethanesulfonyl)aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(furan-2-yl)carbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(thiophen-2-yl)carbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(1-methyl-1H-pyrrol-2-yl)carbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(furan-3-yl)carbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(tetrahydrofuran-2-yl)carbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(tetrahydrofuran-3-yl)carbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(tetrahydropyran-4-yl)carbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(2-cyclopropylacetyl)-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(2-hydroxyethyl)carbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-methoxyacetyl-N-trifluoromethanesulfonyl)aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-ethoxyacetyl-N-trifluoromethanesulfonyl)aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(2-methoxyethyl)carbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(2-tert-butyldimethylsilyloxyethyl)carbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-acetoxyacetyl-N-trifluoromethanesulfonyl)aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-methylsulfylacetyl-N-trifluoromethanesulfonyl)aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-ethylsulfylacetyl-N-trifluoromethanesulfonyl)aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(1-methylsulfilethyl)carbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-methoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-8-fluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-8-cyclopropyl-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-8-cyano-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-8-hydroxy-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-8-phenyl-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-5-methyl-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-8-fluoro-6-methyl-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-6-cyclopropyl-8-fluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-6-cyano-8-fluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-5-bromo-8-fluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-8-fluoro-5-methyl-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-8-fluoro-5-trifluoromethyl-3,44-dihydroisoquinolin-1(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-8-fluoro-5-methoxy-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-8-chloro-5-fluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-8-dimethylamino-5-fluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-5-fluoro-8-(N-morpholinyl)-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-5-fluoro-8-methylthio-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-5,8-bis(methylthio)-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-5-fluoro-8-methanesulfonyl-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-5,6-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(1-propyl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(2-propyl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(1-butyl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(2-methyl-1-propyl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(2-butyl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(1,1-dimethyl-ethyl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(1-pentyl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(1-hexyl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(1-heptyl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(2,2-dimethyl-1-propyl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(chloromethyl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(trichloromethyl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(1-chloroethyl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(2-fluoroethyl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-8-fluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(2-fluoroethyl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(2,2-difluoroethyl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(2,2-difluoroethyl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-8-fluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(2,2-difluoroethyl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(2,2,2-trifluoroethyl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(2-chloroethyl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(2,2-difluoro-1-methyl-ethyl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(2,2,2-trifluoro-1-methyl-ethyl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(1,3-difluoropropan-2-yl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-cyclopropyloxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-cyclobutyloxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-cyclopentyloxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-cyclohexyloxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-allyloxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(but-3-en-2-yl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(2-methylallyl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(3-methylbut-2-en-1-yl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-propargyloxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(but-3-yn-2-yl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-phenoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(4-nitrophenoxy)carbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,44-dihydroisoquinolin-1(2H)-one, N-[2-[N-(oxetan-3-yl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(oxetan-3-yl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-8-fluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(oxetan-3-yl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(tetrahydrofuran-3-yl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(tetrahydrofuran-3-yl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-((S)-tetrahydrofuran-3-yl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-((R)-tetrahydrofuran-3-yl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(tetrahydrothiophen-3-yl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(1,1-dioxidetetrahydrothiophen-3-yl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(tetrahydro-2H-pyran-3-yl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(tetrahydro-2H-pyran-4-yl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(1,3-dioxan-5-yl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(2,2-dimethyl-1,3-dioxan-5-yl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(tetrahydro-2H-thiopyran-4-yl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(1,1-dioxidetetrahydro-2H-thiopyran-4-yl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(2,5-dioxopyrrolidin-1-yl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(cyclopropylmethyloxy)carbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-benzyloxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(oxiran-2-ylmethyl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-[(2-methyloxiran-2-yl)methyl]oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one4-dihydroisoquinolin-1(2H)-one, N-[2-[N-[(3,3-dimethyloxiran-2-yl)methyl]oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-[1-(oxiran-2-yl)ethyl]oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(oxetan-2-ylmethyl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-(oxetan-3-ylmethyl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-[(tetrahydrofuran-2-yl)methyl]oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-[(tetrahydrofuran-3-yl)methyl]oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-[(tetrahydro-2H-pyran-2-yl)methyl]oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-[(tetrahydro-2H-pyran-4-yl)methyl]oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-[(2-oxo-1,3-dioxolan-4-yl)methyl]oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-[(5-methyl-2-oxo-1,3-dioxol-4-yl)methyl]oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(2-cyano-ethoxy)carbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(2-hydroxy-ethoxy)carbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(2-methoxy-ethoxy)carbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(1-methyl-2-methoxyethoxy)carbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(1,3-dimethoxypropan-2-yl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-[2-(tert-butyldiphenylsilyloxy)ethyl]oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-[2-(acetyloxy)ethoxy]carbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-[2-(methanesulfonyloxy)ethoxy]carbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(2-oxopropyl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(methoxycarbonylmethoxycarbonyl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(2-methylthio-ethoxy)carbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(2-methanesulfonyl-ethoxy)carbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(2-propylthio)carbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(2-propylthio)carbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-8-fluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-ethylthio-carbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(2-propylthio)carbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(2-butyl)thio-carbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-methylaminocarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(2-propylamino)carbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-dimethylaminocarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one4-dihydroisoquinolin-1(2H)-one, N-[2-(N-methanesulfonyl-N-trifluoromethanesulfonyl)aminobenzyl]-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-methanesulfonyl-N-trifluoromethanesulfonyl)aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-methanesulfonyl-N-trifluoromethanesulfonyl)aminobenzyl]-5-fluoro-8-hydroxy-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-ethanesulfonyl-N-trifluoromethanesulfonyl)aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N,N-bis(trifluoromethanesulfonyl)]aminobenzyl]-8-hydroxy-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N,N-bis(trifluoromethanesulfonyl)]aminobenzyl]-8-propargyloxy-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N,N-bis(trifluoromethanesulfonyl)]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-cyclopropanesulfonyl-N-trifluoromethanesulfonyl)aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, sodium [2-[(5,8-difluoro-1-oxo-3,4-dihydroisoquinolin-2(1H)-yl)methyl]phenyl][(trifluoromethyl)sulfonyl]amide, potassium [2-[(5,8-difluoro-1-oxo-3,4-dihydroisoquinolin-2(1H)-yl)methyl]phenyl][(trifluoromethyl)sulfonyl]amide, N-[2-(N-trifluoromethanesulfonyl)amino-3-chloro-benzyl]-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)amino-4-methyl-benzyl]-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)amino-4-methoxy-benzyl]-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)amino-5-fluoro-benzyl]-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)amino-5-chloro-benzyl]-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)amino-5-bromo-benzyl]-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)amino-5-methyl-benzyl]-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)amino-6-chloro-benzyl]-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)amino-3,5-dichloro-benzyl]-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)amino-5-chloro-benzyl]-8-chloro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)amino-5-chloro-benzyl]-6-chloro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)amino-3-fluoro-benzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)amino-3-chloro-benzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)amino-3-methyl-benzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)amino-4-fluoro-benzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)amino-5-fluoro-benzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)amino-5-chloro-benzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)amino-5-methyl-benzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)amino-5-hydroxy-benzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)amino-5-methoxy-benzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)amino-6-fluoro-benzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)amino-6-chloro-benzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)amino-6-methyl-benzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)amino-naphthalen-3-yl-methyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)amino-5-chloro-benzyl]-8-chloro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)amino-3-fluoro-benzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)amino-3-chloro-benzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)amino-3-methyl-benzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)amino-4-fluoro-benzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one4-dihydroisoquinolin-1(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)amino-5-fluoro-benzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)amino-5-chloro-benzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)amino-5-methyl-benzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)amino-5-trifluoromethyl-benzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)amino-5-hydroxy-benzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)amino-5-methoxy-benzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)amino-6-fluoro-benzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)amino-6-chloro-benzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)amino-6-methyl-benzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)amino-naphthalen-3-yl-methyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-pent-1-yloxycarbonyl-N-trifluoromethanesulfonyl)amino-4-fluoro-benzyl]-5,8-difluoro-3,44-dihydroisoquinolin-1(2H)-one, N-[2-(N-pent-1-yloxycarbonyl-N-trifluoromethanesulfonyl)amino-5-fluoro-benzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-pent-1-yloxycarbonyl-N-trifluoromethanesulfonyl)amino-6-fluoro-benzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-2,3,4,5-tetrahydro-1H-2-benzazepin-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-9-chloro-2,3,4,5-tetrahydro-1H-2-benzazepin-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-9-methyl-2,3,4,5-tetrahydro-1H-2-benzazepin-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-fluoro-2,3,4,5-tetrahydro-1H-2-benzazepin-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-chloro-2,3,4,5-tetrahydro-1H-2-benzazepin-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-methyl-2,3,4,5-tetrahydro-1H-2-benzazepin-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-4,5-dihydro-6H-thieno[2,3-c]pyrrol-6-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-2-bromo-4,5-dihydro-6H-thieno[2,3-c]pyrrol-6-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-2-(methylthio)-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-5-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5,6-dihydrofurano[2,3-c]pyrimidin-7(4H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5,6-dihydrothieno[2,3-c]pyridin-7(4H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-6,7-dihydrothieno[3,2-c]pyridin-4(5H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-3-methyl-5,6-dihydroisoxazolo[5,4-c]pyridin-7(4H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-2-methyl-6,7-dihydrooxazolo[5,4-c]pyridin-4(5H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-6,7-dihydrooxazolo[4,5-c]pyridin-4(5H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-2-methyl-6,7-dihydrooxazolo[4,5-c]pyridin-4(5H)-one, 5-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-1,5,6,7-tetrahydro-4H-pyrazolo[4,3-c]pyridin-4-one, 5-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-1-methyl-1,5,6,7-tetrahydro-4H-pyrazolo[4,3-c]pyridin-4-one, 5-[2-(N-trifluoromethanesulfonyl)aminobenzyl]3-bromo-1-methyl-1,5,6,7-tetrahydro-4H-pyrazolo[4,3-c]pyridin-4-one, 5-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-3-methyl-1-phenyl-1,5,6,7-tetrahydro-4H-pyrazolo[4,3-c]pyridin-4-one, 5-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-3-methyl-1-(pyridin-2-yl)-1,5,6,7-tetrahydro-4H-pyrazolo[4,3-c]pyridin-4-one, 5-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-2-methyl-2,5,6,7-tetrahydro-4H-pyrazolo[4,3-c]pyridin-4-one, 5-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-2,3-dimethyl-2,5,6,7-tetrahydro-4H-pyrazolo[4,3-c]pyridin-4-one, 5-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-3-bromo-2-methyl-2,5,6,7-tetrahydro-4H-pyrazolo[4,3-c]pyridin-4-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-6,7-dihydro-1,7-naphthyridin-8(5H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-3,4-dihydro-2,6 naphthyridin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-2-methyl-7,8-dihydropyrido[4,3-d]pyrimidin-5(6H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-5,6-dihydrothieno[2,3-c]pyridin-7(4H)-one, 5-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-3-bromo-1-methyl-1,5,6,7-tetrahydro-4H-pyrazolo[4,3-c]pyridin-4-one, 5-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-2,3-dimethyl-2,5,6,7-tetrahydro-4H-pyrazolo[4,3-c]pyridin-4-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-6,7-dihydro-1,7-naphthyridin-8(5H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-3,4-dihydro-2,6-naphthyridin-1(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-7,8-dihydro-1,6-naphthyridin-5(6H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-3,4-dihydroisoquinoline-1(2H)-thione, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-thione, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-3-methyl-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-3,3-dimethyl-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-2,2-dimethyl-2,3-dihydro-4H-benzo[e][1,3]oxazin-4-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-1H-benzo[d][1,2]oxazin-4(3H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-2,3-dihydro-4H-benzo[e][1,3]thiazin-4-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-4-methyl-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-4-methyl-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-4,4-dimethyl-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-4-methoxyisoquinolin-1(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethylsulfonyl)aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-thione, N-[2-(N-ethoxycarbonyl-N-trifluoromethylsulfonyl)aminobenzyl]-3-methyl-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethylsulfonyl)aminobenzyl]-1H-benzo[d][1,2]oxazin-4(3H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethylsulfonyl)aminobenzyl]-4-methyl-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethylsulfonyl)aminobenzyl]-4,4-dimethyl-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethylsulfonyl)aminobenzyl]-isoquinolin-1(2H)-one, N-[2-(N-trifluoromethylsulfonyl)amino-phenylethan-1-yl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-difluoromethanesulfonyl)aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-1,3-dihydroindol-2-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5-fluoro-1,3-dihydroindol-2-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5-chloro-1,3-dihydroindol-2-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5-bromo-1,3-dihydroindol-2-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-6-chloro-1,3-dihydroindol-2-one, N-[2-(N-trifluoromethanesulfonyl)amino-5-trifluoromethyl-benzyl]-1,3-dihydroindol-2-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-1,3-dihydroindol-2-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-5-fluoro-1,3-dihydroindol-2-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-5-chloro-1,3-dihydroindol-2-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-5-bromo-1,3-dihydroindol-2-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-6-chloro-1,3-dihydroindol-2-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)amino-5-trifluoromethyl-benzyl]-1,3-dihydroindol-2-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-1,4-dihydroisoquinolin-3(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-3,4-dihydroquinolin-2(1H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-3-methyl-3,4-dihydroquinazolin-2(1H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-phenanthridin-6(5H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-1,4-dihydroisoquinolin-3(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-3,4-dihydroquinolin-2(1H)-one, 1-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-3-methyl-3,4-dihydroquinazolin-2(1H)-one, and The herbicidal composition according to (1), wherein the herbicidal composition is selected from the group consisting of N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-phenanthridin-6(5H)-one.

[0013] (8) The herbicidal composition according to any one of (1) to (7), wherein the compound represented by the formula [1] is a mixture of enantiomers or a mixture of diastereoisomers.

[0014] (9) The herbicidal composition according to any one of (1) to (8), wherein the component (b) comprises at least one selected from the group consisting of an ALS inhibitor, a germination / elongation suppressor, a photosynthesis inhibitor, a PPO inhibitor, a bleaching agent, a VLCFAs inhibitor, a hormone action inhibitor / disruptor, and an ACCase inhibitor.

[0015] (10) The ALS inhibitor is selected from the group consisting of amidosulfuron, azimsulfuron, bensulfuron-methyl, bispyribac, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cloransulam-methyl, cyclosulfamuron, and dichlorosulfamuron. Diclosulam, ethametsulfuron-methyl, ethoxysulfuron, flazasulfuron, florasulam, flucarbazone, flumetsulam, flupyrsulfuron-methyl, foramsulfuron, halosulfuron-methyl n-methyl), imazamethabenzmethyl, imazamox, imazapic, imazapyr, imazaquin, imazethapyr, imazosulfuron, iodosulfuron-methyl, iofensulfuron, iofensulfuron sodium sodium), metazosulfuron, metsulfuron-methyl, nicosulfuron, orthosulfamuron, oxasulfuron, penoxsulam, primisulfuron-methyl, propoxycarbazone, propyrisulfuron,Prosulfuron, pyrazosulfuron-ethyl, pyribenzoxim, pyriftalid, pyriminobac-methyl, pyrimisulfan, pyrithiobac, rimsulfuron, sulfometuron-methyl, sulfosulfuron, chienka at least one selected from the group consisting of thiencarbazone-methyl, thifensulfuron-methyl, triafamone, triasulfuron, tribenuron-methyl, trifloxysulfuron, triflusulfuron-methyl, and tritosulfuron; The germination and elongation inhibitor is selected from the group consisting of benfluralin, bromobutide, butamifos, butralin, carbetamide, chlorpropham, chlorthal-dimethyl, cumyluron, dichlobenil, dinitramine, dithiopyr, and dimethicone. ron (dymron), ethalfluralin (ethalfluralin), etobenzanide (etobenzanid), methiozolin (methiozolin), methyldymron (methyldymron), oryzalin (oryzalin), oxaziclomefone (oxaziclomefone), pendimethalin (pendimethalin), propham (propham), propyzamide (propyzamide), pyributicarb (pyributicarb), sodium chlorate (sodium chlorate),The present invention relates to a method for producing a plant protection system using a photosynthesis inhibitor, the method comprising the step of: (a) introducing a photoactivatable agent containing at least one selected from the group consisting of tetflupyrolimet, thiazopyr, triaziflam, and trifluralin; and (b) providing a method for producing a plant protection system using a photosynthesis inhibitor containing at least one selected from the group consisting of ametryn, atrazine, bentazon, bromacil, bromoxynil, bromofenoxim, chlorbromuron, chloridazon, chlorotoluron, chloroxuron, and cyanazine. , desmedipham (desmedipham), desmetrin (desmetryn), dimefuron (dimefuronn), dimethametryn (dimethametryn), diuron (dioron), ethidimuron (ethidimuron), fenuron (fenuron), fluometuron (fluometuron), hexazinone (hexazinone), ioxynil (ioxynil), isoproturon (isoproturon), isouron (isouron), Carbutyrate, lenacil, linuron, metamitron, methabenzthiazuron, metobromuron, metoxuron, metribuzin, monolinuron, neburon, pentanochlor, phenmede phenmedipham, prometon, prometryn, propanil, propazine, pyridafol, pyridate, quinoclamine, siduron, simazine, simetryn, tebuthiuron, terbacil,At least one selected from the group consisting of terbumeton, terbuthylazine, terbutryn, and trietazine; The PPO inhibitor is selected from the group consisting of acifluorfen, azafenidin, benzfendizone, bifenox, butafenacil, carfentrazone-ethyl, chlomethoxyfen, chlorphthalim, cinidon-ethyl, cyclopyranil, fluazolate, flufenpyr-ethyl, flumiclorac-pentyl, flumioxazin, fluoroglycophen, fluoroisopropyl methyl ... Fluoroglycofen-ethyl, fluthiacet-methyl, fomesafen, halosafen, lactofen, oxadiazon, oxadiargyl, oxyfluorfen, pentoxide, at least one selected from the group consisting of pentoxazone, profluazol, pyraclonil, pyraflufen-ethyl, saflufenacil, sulfentrazone, and thidiazimin; The whitening agent is selected from the group consisting of aclonifen, amitrole, beflubutamid, benzobicyclon, benzofenap, bicyclopyrone, clomazone, cyclopyrimorate,Diflufenican, fenquinotrione, fluridone, flurochloridone, flurtamone, iptriazopyride, isoxachlortole, isoxaflutole, mesotrione, norflurazo at least one selected from the group consisting of norflurazon, picolinafen, pyrasulfotole, pyrazolate, pyrazoxyfen, sulcotrione, tefuryltrione, tembotrione, and topramezone; The VLCFAs inhibitors include acetochlor, alachlor, anilofos, benfuresate, butachlor, butyrate, cafenstrole, dimepiperate, dimesulfazet, dimethachlor, dimethenamid, dimethenamid-P, EPTC, esprocarb, ethofumesse, ethofumesate, fenoxasulfone, fentrazamide, flufenacet, hexylthiocarbam, indanofan, ipfencarbazone, mefenacet, metazachlor, molinate, orbencarb, pebulate, pesoxamid, piperophos,At least one selected from the group consisting of pretilachlor, propachlor, propisochlor, prosulfocarb, pyroxasulfone, S-metolachlor, thenylchlor, thiobencarb, thiocarbazil, triallate, and vernolate; The hormone action inhibitor / disruptor is 2,3,6-TBA, 2,4-D, 2,4-DB, 2,4-PA ethyl (2,4-PA-ethyl), aminocyclopyrachlor, aminopyralid, benazolin, chloramben, clomeprop, clopyralid, dicamba, dichlorprop, diflufenzopyr, , florpyrauxifen-benzyl, fluroxypyr-1-methylheptylester, MCPA, MCPB, mecoprop, naptalam, phenothiol, picloram, quinclorac, quinmerac, and triclopyr, The ACCase inhibitor is selected from the group consisting of alloxydim, butroxydim, clethodim, clodinafop-propargyl, cycloxydim, cyhalofop-butyl, diclofop-methyl, fenoxaprop-P-ethyl,The herbicidal composition according to (9), comprising at least one selected from the group consisting of fluazifop-P-butyl, haloxyfop-P-methyl, metamifop, pinoxaden, profoxydim, propaquizafop, quizalofop-P-ethyl, sethoxydim, tepraloxydim, and tralkoxydim.

[0016] (11) The ALS inhibitor includes at least one selected from the group consisting of bispyribac, metazosulfuron, penoxsulam, pyrimisulfan, propyrisulfuron, sulfometuron-methyl, and triafamone, and the germination and elongation inhibitor includes bromobutide, dymron, methiozolin, sodium chlorate, or the like. the photosynthesis inhibitor comprises at least one selected from the group consisting of bentazone, carbutilate, and propanil; the PPO inhibitor comprises at least one selected from the group consisting of carfentrazone-ethyl, cyclopyranil, oxadiargyl, pentoxazone, and pyraclonil; The whitening agent comprises at least one selected from the group consisting of benzobicyclon, clomazone, cyclopyrimorate, fenquinotrione, iptriazopyrid, mesotrione, and tefuryltrione;The VLCFAs inhibitor comprises at least one selected from the group consisting of benfuresate, cafenstrole, dimesulfazet, fenoxasulfone, fentrazamide, ipfencarbazone, and thenylchlor, and the hormone action inhibitor / disruptor comprises at least one selected from the group consisting of florpyrauxifen-benzyl and quinclorac, The herbicidal composition according to (10), wherein the ACCase inhibitor comprises at least one selected from the group consisting of cyhalofop-butyl and metamifop.

[0017] (12) The herbicidal composition according to any one of (1) to (11), which is used as an agricultural or horticultural herbicide.

[0018] (13) A method for controlling plant pests, comprising a step of applying (a) the compound represented by formula [1] described in (1) or a salt thereof, and (b) an agricultural or horticultural herbicide to a plant or an area surrounding the plant in an agricultural or non-agricultural land, wherein the component (a) and the component (b) are applied simultaneously, successively, or separately.

[0019] (14) The method for controlling plant pests according to (13), wherein the treatment is at least one selected from the group consisting of spraying, dusting, dusting, spraying, diffusing, dipping, irrigating, injecting, sprinkling (immersion), foaming, applying, dusting, coating, spraying, fumigating, fumigating, smoking, misting, and painting.

[0020] (15) The method for controlling plant pests according to (13) or (14), wherein the area around the plant is at least one selected from the group consisting of soil, water for hydroponic cultivation, and cultivation materials.

[0021] (16) The herbicidal composition according to any one of (1) to (12) or the method for controlling plant pests according to any one of (13) to (15), wherein the component (b) contains dymron.

[0022] (17) The herbicidal composition according to any one of (1) to (12), which is a herbicidal composition for transplanted paddy rice, wherein the component (b) is a pesticide for transplanted paddy rice.

[0023] (18) The herbicidal composition according to any one of (1) to (12), wherein component (b) is an agricultural chemical for transplanted rice used for controlling weeds selected from annual weeds such as barnyard grass, Japanese sedge, bulrush, water sedge, barnyard grass, barnyard grass, Cyperus galloat, Leptolepis gracilis, Monochoria vaginalis, American dumbbells, dumbbells, Turmeric, Chrysanthemum globosum, Echinochloa japonica, Jerusalem artichoke, Lythrum salicaria, water chickweed, Monochoria korsakowii, Polygonum japonica, Eucalyptus globosum, Eastern chinaberry, Ezo-no-soybean, and Japanese ragwort, and perennial weeds such as Sagittaria pygmaea, Arrowroot, Cyperus serotinus, Euonymus kuroguwai, Bulrush, Arrowroot, Shizu, Siberian clubroot, Potweed, Reed oak, Japanese knotweed, Japanese bean weed, and Japanese sedge.

[0024] (1') (a) Formula [1] {In the formula, A, E, W, o, p, m, n, R １ , R ２ , R ３ , R ４ , X and Y are as defined in (1) above) or a salt thereof, wherein (b) the composition is for use in combination with at least one agricultural and horticultural herbicide.

[0025] (2') (b) A herbicidal composition containing at least one agricultural and horticultural herbicide, (a) a compound represented by the formula [1] {In the formula, A, E, W, o, p, m, n, R １ , R ２ , R ３ , R ４ , X and Y are as defined in (1) above} or a salt thereof.

[0026] (1″) (b) A compound represented by the formula [1] for use in combination with at least one agricultural or horticultural herbicide. {In the formula, A, E, W, o, p, m, n, R １ , R ２ , R ３ , R ４ , X and Y are as defined in the above (1)} or a salt thereof.

[0027] (2'') (a) Formula [1] {In the formula, A, E, W, o, p, m, n, R １ , R ２ , R ３ , R ４ , X and Y are as defined in (1) above} or a salt thereof.

[0028] (2''') The compound represented by the formula [1] or a salt thereof is represented by the formula [1a] {In the formula, E, W, m, n, R １ , R ２ , R ３ , R ４ , X １ , X ２ , X ３ , X ４ , Y １ , Y ２ , Y ３ and Y ４ is as defined in (2) above) or a salt thereof.

[0029] (3''') The compound represented by the formula [1] or a salt thereof is represented by the formula [1a] {In the formula, E, W, m, n, R １ , R ２ , R ３ , R ４ , X １ , X ２ , X ３ , X ４ , Y １ , Y ２ , Y３ and Y ４ is as defined in (3) above} or a salt thereof.

[0030] (4''') In the formula [1a], n is 2, and R １ is trifluoromethyl, R ２ is a hydrogen atom, (C ３ ~C ６ cycloalkyl)carbonyl, (C ２ ~C ４ alkenyl)carbonyl, C １ ~C ６ Alkoxy (C １ ~C ６ alkyl)carbonyl, 2-furylcarbonyl, C １ ~C ６ Alkylthio (C １ ~C ６ alkyl)carbonyl, (C １ ~C ５ alkoxy)carbonyl, (haloC １ ~C ３ alkoxy)carbonyl, (C ３ ~C ４ cycloalkyloxy)carbonyl, (C ２ ~C ３ alkynyloxy)carbonyl, heterocyclyloxycarbonyl, C ３ ~C ４ Cycloalkyl (C １ ~C ２ alkoxy) carbonyl, heterocyclyl (C １ ~C ２ alkoxy)carbonyl, (cyano C １ ~C ６ alkoxy)carbonyl, (hydroxy C １ ~C ６ Alkoxy)carbonyl, C １ ~C ６ Alkoxy (C １ ~C ６ Alkoxy)carbonyl, C １ ~C ２ alkylsulfonyl, or (C１ ~C ４ alkylthio)carbonyl, １ is a fluorine atom, a chlorine atom, or methyl; X ２ and X ３ is a hydrogen atom, and X ４ is a hydrogen atom, a fluorine atom, a chlorine atom, methyl, trifluoromethyl, or methoxy; １ , Y ２ , Y ３ and Y ４ is a hydrogen atom, and the heterocyclyl is oxiranyl, oxetanyl, tetrahydrofuranyl, or tetrahydropyranyl. The herbicidal composition or use according to (3''').

[0031] (5''') The compound represented by the formula [1] or a salt thereof is represented by the formula [1b] {wherein Het, E, W, m, n, R １ , R ２ , R ３ , R ４ , Y １ , Y ２ , Y ３ and Y ４ is as defined in (5) above} or a salt thereof.

[0032] (6''') In the formula [1b], Het is Het-1 or Het-2, n is 2, and R １ is trifluoromethyl, R ２ is a hydrogen atom or (C ２ ~C ６ The herbicidal composition or use according to (5'''), wherein the aryl group is a hydroxyl group or a hydroxyl group.

[0033] (7''') The herbicidal composition according to (1') or (2'), or the use according to (1'') or (2''), wherein the compound represented by formula [1] or a salt thereof is selected from the group defined in (7) above.

[0034] (8''') The herbicidal composition according to any one of (1'), (2') and (2''') to (7'''), or the use according to any one of (1'', (2'') and (2''') to (7'''), wherein the compound represented by formula [1] is a mixture of enantiomers or a mixture of diastereoisomers.

[0035] (9''') The herbicidal composition according to any one of (1'), (2') and (2''') to (8'''), or the use according to any one of (1'', (2'') and (2''') to (8'''), wherein the component (b) comprises at least one selected from the group consisting of an ALS inhibitor, a germination / elongation suppressor, a photosynthesis inhibitor, a PPO inhibitor, a bleaching agent, a VLCFAs inhibitor, a hormone action inhibitor / disruptor, and an ACCase inhibitor.

[0036] (10''') The herbicidal composition or use according to (9'''), wherein the ALS inhibitor comprises at least one selected from the group defined in (10) above, the germination / elongation inhibitor comprises at least one selected from the group defined in (10) above, the photosynthesis inhibitor comprises at least one selected from the group defined in (10) above, the PPO inhibitor comprises at least one selected from the group defined in (10) above, the bleaching agent comprises at least one selected from the group defined in (10) above, the VLCFAs inhibitor comprises at least one selected from the group defined in (10) above, the hormone action inhibitor / disruptor comprises at least one selected from the group defined in (10) above, and the ACCase inhibitor comprises at least one selected from the group defined in (10) above.

[0037] (11''') The herbicidal composition or use according to (10'''), wherein the ALS inhibitor comprises at least one selected from the group defined in (11) above, the germination / elongation inhibitor comprises at least one selected from the group defined in (11) above, the photosynthesis inhibitor comprises at least one selected from the group defined in (11) above, the PPO inhibitor comprises at least one selected from the group defined in (11) above, the bleaching agent comprises at least one selected from the group defined in (11) above, the VLCFAs inhibitor comprises at least one selected from the group defined in (11) above, the hormone action inhibitor / disruptor comprises at least one selected from the group defined in (11) above, and the ACCase inhibitor comprises at least one selected from the group defined in (11) above.

[0038] (12''') The herbicidal composition according to any one of (1'), (2') and (2''') to (10'''), or the use according to any one of (1'', (2'') and (2''') to (10'''), wherein the herbicidal composition is used as an agricultural or horticultural herbicide.

[0039] (13"") A method for controlling undesirable plants for useful plants and useful crops, comprising a step of applying (a) the compound represented by formula [1] described in (1) or a salt thereof, and (b) an agricultural or horticultural herbicide to plants or areas surrounding the plants in agricultural or non-agricultural land, wherein the component (a) and the component (b) are applied simultaneously, successively, or separately.

[0040] (14"") The method for controlling undesirable plants for useful plants and useful crops according to (13""), wherein the treatment is at least one selected from the group consisting of spraying, dusting, dusting, spraying, diffusing, dipping, irrigating, injecting, sprinkling (drenching), foaming, spreading, applying, dusting, coating, spraying, fumigating, smoking, misting, and painting.

[0041] (15'''') The method for controlling undesirable plants for useful plants and useful crops according to (13'''') or (14''''), wherein the area around the plants is at least one selected from the group consisting of soil, water for hydroponic cultivation, and cultivation materials.

[0042] (16'''') The herbicidal composition according to any one of (1) to (12) or the method for controlling undesirable plants for useful plants and useful crops according to any one of (13'''') to (15''''), wherein the component (b) contains dymron.

[0043] According to the present invention, a mixture of the active ingredients of the herbicide, component (a): a compound represented by formula [1] or a salt thereof (hereinafter referred to as compound A), and component (b): an agricultural and horticultural herbicide (hereinafter referred to as compound B), complements each other's herbicidal spectrum without antagonism and also exhibits a synergistic effect. For these reasons, the present invention is extremely useful in practical situations.

[0044] The present invention will be described in detail below. Compound A of the present invention includes not only the haloalkylsulfonanilide compound represented by formula [1] but also salts of the compound. Compound A may be in the form of a hydrate or solvate and may have a specific crystalline polymorphism. The salt of Compound A is not particularly limited, and examples thereof include salts acceptable for agricultural chemical production, specifically sodium salt, potassium salt, magnesium salt, calcium salt, aluminum salt, etc. Furthermore, all possible stereoisomers or optical isomers of Compound A of the present invention, as well as mixtures containing two or more of these isomers in any ratio, are also included within the scope of Compound A (the haloalkylsulfonanilide compound represented by formula [1]). Formula [1] provides a specific definition of Compound A of the present invention. Preferred definitions of groups related to the formulas shown in this specification are described below. These definitions apply to the final product represented by formula [1], and similarly apply to all synthetic intermediates.

[0045] Preferred embodiments are described below. A is an optionally substituted benzene ring or heteroaromatic ring, preferably an optionally substituted benzene ring. E is preferably -C(R ５ ) (R ６ ) -, an oxygen atom, or a sulfur atom, and more preferably -CH ２ -. o is preferably 0 to 3, more preferably 0 to 2. p is preferably 0 to 3, more preferably 0. m is preferably 0 or 1, more preferably 0. n is preferably 1 to 3, more preferably 2.

[0046] R １ is preferably fluoro C １ ~C ６ R is preferably alkyl, and more preferably trifluoromethyl. ２ is preferably a hydrogen atom, (C ３ ~C ６ cycloalkyl)carbonyl, (C ２ ~C ４ alkenyl)carbonyl, (C １ ~C ５ Alkoxy) carbonyl, halo C １ ~C ３ alkoxy)carbonyl, (C ３ ~C ４ cycloalkyloxy)carbonyl, heterocyclyloxycarbonyl, C ３ ~C ４ Cycloalkyl (C １ ~C ２ alkoxy) carbonyl, heterocyclyl (C １ ~C ２ Alkoxy)carbonyl, C １ ~C ２ alkylsulfonyl, or (C １ ~C ４ alkylthio)carbonyl, more preferably a hydrogen atom, (C ３ ~C ６ cycloalkyl)carbonyl, (C １ ~C ５ alkoxy)carbonyl, (haloC １ ~C ３alkoxy)carbonyl, heterocyclyloxycarbonyl, heterocyclyl (C １ ~C ２ alkoxy)carbonyl, or methanesulfonyl.

[0047] R ３ and R ４ are preferably, independently of one another, a hydrogen atom, C １ ~C ４ Alkyl or haloC １ ~C ４ R is preferably an alkyl group, and more preferably a hydrogen atom. ５ and R ６ are preferably, independently of one another, a hydrogen atom, C １ ~C ４ Alkyl or haloC １ ~C ４ R is preferably an alkyl group, and more preferably a hydrogen atom. ７ is preferably C １ ~C ４ It is preferably alkyl or phenyl, more preferably methyl.

[0048] Z １ C optionally substituted with one or more substituents selected from １ ~C ６ Examples of alkyl include C １ ~C ６ Alkyl, haloC １ ~C ６ Alkyl, C ３ ~C ６ Cycloalkyl C １ ~C ６ Alkyl, phenyl C １ ~C ６ Alkyl, heterocyclyl C １ ~C ６ Alkyl, heterocyclyl C １ ~C ６ Alkyl, cyano C １ ~C ６ Alkyl, C １ ~C ６ Alkoxy C １ ~C ６ Alkyl, haloC １ ~C ６ Alkoxy C１ ~C ６ Alkyl, C ３ ~C ６ Cycloalkyloxy C １ ~C ６ Alkyl, (phenoxy)C １ ~C ６ Alkyl, (phenyl C １ ~C ６ Alkoxy C １ ~C ６ Alkyl, Tri C １ ~C ６ Alkylsilyl C １ ~C ６ Alkoxy C １ ~C ６ Alkyl, C １ ~C ６ Alkyldiphenylsilyl C １ ~C ６ Alkoxy C １ ~C ６ Alkyl, phenylcarbonyloxy C １ ~C ６ Alkyl, heterocyclylcarbonyloxy C １ ~C ６ Alkyl, C １ ~C ６ Alkoxy C １ ~C ６ Alkoxy C １ ~C ６ Alkyl, haloC １ ~C ６ Alkoxy C １ ~C ６ Alkoxy C １ ~C ６ Alkyl, phenylcarbonyloxy C １ ~C ６ Alkoxy C １ ~C ６ Alkyl, (C １ ~C ６ Alkyl)carbonyloxy C １ ~C ６ Alkyl, (haloC １ ~C ６ Alkyl)carbonyloxy C １ ~C ６ Alkyl, (C ３ ~C ６Cycloalkyl)carbonyloxy C １ ~C ６ Alkyl, (C １ ~C ６ Alkoxy)carbonyloxy C １ ~C ６ Alkyl, phenoxycarbonyloxy C １ ~C ６ Alkyl, mono(C １ ~C ６ Alkyl)aminocarbonyloxy C １ ~C ６ Alkyl, di(C １ ~C ６ Alkyl)aminocarbonyloxy C １ ~C ６ Alkyl, phenylaminocarbonyloxy C １ ~C ６ Alkyl, C １ ~C ６ Alkyl(phenyl)aminocarbonyloxy C １ ~C ６ Alkyl, C １ ~C ６ Alkylthio C １ ~C ６ Alkyl, haloC １ ~C ６ Alkylthio C １ ~C ６ Alkyl, C １ ~C ６ Alkylsulfinyl C １ ~C ６ Alkyl, haloC １ ~C ６ Alkylsulfinyl C １ ~C ６ Alkyl, C １ ~C ６ Alkylsulfonyl C １ ~C ６ Alkyl, haloC １ ~C ６ Alkylsulfonyl C １ ~C ６ Alkyl, phenylthio C １ ~C ６ Alkyl, phenylsulfinyl C １ ~C ６ Alkyl, phenylsulfonyl C１ ~C ６ Alkyl, phenyl C １ ~C ６ Alkylthio C １ ~C ６ Alkyl, phenyl C １ ~C ６ Alkylsulfinyl C １ ~C ６ Alkyl, phenyl C １ ~C ６ Alkylsulfonyl C １ ~C ６ Alkyl, thiocyanato C １ ~C ６ Alkyl, (C １ ~C ６ Alkyl)carbonyl C １ ~C ６ Alkyl, (haloC １ ~C ６ Alkyl)carbonyl C １ ~C ６ Alkyl, (C １ ~C ６ Alkoxy)carbonyl C １ ~C ６ Alkyl, (haloC １ ~C ６ Alkoxy)carbonyl C １ ~C ６ Alkyl, phenylcarbonyl C １ ~C ６ alkyl, etc., wherein the phenyl and heterocyclyl moieties contained in the above groups are independently Z ２ may be substituted with one or more substituents selected from:

[0049] Z １ is preferably C ３ ~C ６ cycloalkyl, Z ２ phenyl optionally substituted by one or more substituents selected from ２ heterocyclyl, cyano, Z ３ C optionally substituted with one or more substituents selected from １ ~C ６ Alkoxy, C ３~C ６ cycloalkyloxy, Z ２ phenoxy optionally substituted by one or more substituents selected from １ ~C ６ alkylsulfonyl, optionally substituted with one or more halogen atoms (C １ ~C ６ alkyl)carbonyl, or (C １ ~C ６ alkoxy)carbonyl, more preferably cyano, Z ３ C optionally substituted with one or more substituents selected from １ ~C ６ Alkoxy, C optionally substituted with one or more halogen atoms １ ~C ６ alkylsulfonyl, or optionally substituted with one or more halogen atoms (C １ ~C ６ alkyl)carbonyl.

[0050] Z ２ is preferably a halogen, C １ ~C ６ Alkyl, haloC １ ~C ６ Alkyl C １ ~C ６ Alkoxy, HaloC １ ~C ６ Alkoxy, (C １ ~C ６ alkyl)carbonyl, (C １ ~C ６ alkyl) carbonyl, (haloC １ ~C ６ alkyl)carbonylcyano, or nitro, more preferably halogen, C １ ~C ６ It is alkyl, cyano, or nitro.

[0051] Z ３ is preferably a halogen atom, triC １ ~C ６ Alkylsilyl, C １ ~C６ alkyldiphenylsilyl, or C optionally substituted by one or more halogen atoms １ ~C ６ Alkoxy, more preferably a halogen atom, triC １ ~C ６ alkylsilyl, or C optionally substituted with one or more halogen atoms １ ~C ６ It is an alkoxy.

[0052] Z ４ is preferably Z ２ Z is phenyl which may be substituted by one or more substituents selected from ６ is preferably di(C １ ~C ６ alkyl)aminocarbonyl, hydroxy, amino, cyano, or nitro, and more preferably cyano or nitro.

[0053] Z ７ is preferably a halogen, C １ ~C ６ Alkyl, C ３ ~C ６ Cycloalkyl, haloC １ ~C ６ Alkyl, C １ ~C ６ Alkoxy, HaloC １ ~C ６ Alkoxy, C １ ~C ６ Alkyl sulfonyl, halo C １ ~C ６ Alkylsulfonyl, (C １ ~C ６ alkyl)carbonyl, (C １ ~C ６ alkoxy), carbonyl, cyano, or nitro, and more preferably halogen, C １ ~C ６ Alkyl, C １ ~C ６ It is alkoxy, cyano, or nitro.

[0054] Z ８ is preferably Z ２phenylthio optionally substituted by one or more substituents selected from ２ and more preferably Z ２ and phenylsulfonyl, which may be substituted by one or more substituents selected from:

[0055] Preferably, X's are each independently a hydrogen atom, a halogen, a methyl, a methoxy, a propargyloxy, a trifluoromethyl, or a trifluoromethoxy, and more preferably, X's are each independently a hydrogen atom, a halogen, or a methyl.

[0056] X １ is preferably a hydrogen atom, halogen, methyl, trifluoromethyl, or methoxy, and more preferably a fluorine atom or a chlorine atom. ２ and X ３ are preferably each independently a hydrogen atom, a halogen atom, a methyl group, a trifluoromethyl group, or a methoxy group, and more preferably a hydrogen atom. ４ is preferably a hydrogen atom, halogen, methyl, trifluoromethyl, or methoxy, and more preferably a hydrogen atom, a fluorine atom, or a chlorine atom.

[0057] Preferably, Y's are each independently a hydrogen atom, halogen, methyl, or trifluoromethyl, and more preferably a hydrogen atom.

[0058] Y １ , Y ２ , Y ３ and Y ４ are preferably each independently a hydrogen atom, halogen, methyl, or trifluoromethyl, and more preferably a hydrogen atom.

[0059] W is an oxygen atom or a sulfur atom, preferably an oxygen atom. The heterocycle is preferably thienyl, furyl, oxiranyl, oxetanyl, tetrahydrofuranyl, or tetrahydropyranyl, more preferably oxiranyl, oxetanyl, or tetrahydrofuranyl. The heteroaromatic ring is preferably selected from the group consisting of Het-1 to Het-18 described above, more preferably Het-1 or Het-2.

[0060] The definitions and explanations of groups given above in the general ranges or preferred ranges can be combined with each other as necessary, i.e., the ranges and preferred ranges can be combined with each other as well. They apply to both the final products and the corresponding precursors and synthetic intermediates.

[0061] Preferred is a compound represented by the formula [1] {wherein R １ Further preferred is a compound represented by the formula [1] {wherein R ２ Further preferred is a compound represented by the formula [1] {wherein R ２ Further preferred is a compound represented by the formula [1] {wherein R ２ Further preferred is a compound represented by the formula [1] {wherein R ２ Further preferred is a compound represented by the formula [1] {wherein R ２ represents (oxetan-3-yl)oxycarbonyl}. Further preferred is a compound represented by the formula [1] {wherein R ２ represents (tetrahydrofuran-3-yl)oxycarbonyl}. Further preferred is a compound represented by formula [1] {wherein R ２ represents (oxiran-2-ylmethyl)oxycarbonyl}. Further preferred is a compound represented by formula [1] {wherein R ２represents (oxetan-2-ylmethyl)oxycarbonyl}. Further preferred is a compound represented by formula [1] {wherein R ２ represents (oxetan-3-ylmethyl)oxycarbonyl}. Further preferred is a compound represented by formula [1] {wherein R ２ represents methanesulfonyl}. Further preferred is a compound represented by formula [1] {wherein W represents an oxygen atom, E is —CH ２ represents -, and R ３ and R ４ represents a hydrogen atom, m represents 0, n represents 2, and X １ represents a fluorine atom, and X ２ , X ３ and X ４ represents a hydrogen atom}. Further preferred is a compound represented by the formula [1] {wherein W represents an oxygen atom, E is —CH ２ represents -, and R ３ and R ４ represents a hydrogen atom, m represents 0, n represents 2, and X １ represents a chlorine atom, and X ２ , X ３ and X ４ represents a hydrogen atom}. Further preferred is a compound represented by the formula [1] {wherein W represents an oxygen atom, E is —CH ２ represents -, and R ３ and R ４ represents a hydrogen atom, m represents 0, n represents 2, and X １ and X ４ represents a fluorine atom, and X ２ and X ３ represents a hydrogen atom}. Further preferred is a compound represented by the formula [1] {wherein W represents an oxygen atom, E is —CH ２ represents -, and R ３ and R ４ represents a hydrogen atom, m represents 0, n represents 2, and X １ and X ４ represents a fluorine atom, and X ２ and X ３represents a hydrogen atom}. Further preferred is a compound represented by the formula [1] {wherein W represents an oxygen atom, E is —CH ２ represents -, and R ３ and R ４ represents a hydrogen atom, m represents 0, n represents 2, and X １ represents a fluorine atom, and X ２ and X ３ represents a hydrogen atom, and X ４ represents a chlorine atom}. Further preferred is a compound represented by the formula [1] {wherein W represents an oxygen atom, E is —CH ２ represents -, and R ３ and R ４ represents a hydrogen atom, m represents 0, n represents 2, and X １ represents a fluorine atom, and X ２ and X ３ represents a hydrogen atom, and X ４ Further preferred is a compound represented by the formula [1] {wherein W represents an oxygen atom, E represents -CH ２ represents -, and R ３ and R ４ represents a hydrogen atom, m represents 0, n represents 2, and X １ represents a fluorine atom, and X ２ and X ３ represents a hydrogen atom, and X ４ Further preferred is a compound represented by formula [1] {wherein W represents an oxygen atom, and E represents -CH ２ represents -, and R ３ and R ４ represents a hydrogen atom, m represents 0, n represents 2, and X １ represents a fluorine atom, and X ２ and X ３ represents a hydrogen atom, and X ４ Further preferred is a compound represented by the formula [1] {wherein W represents a sulfur atom, E represents -CH ２ represents -, and R ３ and R ４ represents a hydrogen atom, m represents 0, n represents 2, and X １ represents a fluorine atom, and X ２ , X３ and X ４ represents a hydrogen atom}. Further preferred is a compound represented by the formula [1] {wherein W represents a sulfur atom, E is —CH ２ represents -, and R ３ and R ４ represents a hydrogen atom, m represents 0, n represents 2, and X １ represents a chlorine atom, and X ２ , X ３ and X ４ represents a hydrogen atom}. Further preferred is a compound represented by the formula [1] {wherein W represents a sulfur atom, E is —CH ２ represents -, and R ３ and R ４ represents a hydrogen atom, m represents 0, n represents 2, and X １ and X ４ represents a fluorine atom, and X ２ and X ３ represents a hydrogen atom}. Further preferred is a compound represented by the formula [1] {wherein W represents a sulfur atom, E is —CH ２ represents -, and R ３ and R ４ represents a hydrogen atom, m represents 0, n represents 2, and X １ and X ４ represents a fluorine atom, and X ２ and X ３ represents a hydrogen atom}.

[0062] In this specification, the following symbols have the following meanings: i: iso, s: secondary, t: tertiary, c: cyclo, p: para.

[0063] The terms used in this specification are explained below. １ ~C ６ The notation with an element symbol and a subscript number such as indicates that the number of elements in the group that follows is in the range indicated by the subscript number. For example, in this case, it indicates that the number of carbon atoms is 1 to 6, and C ２ ~C ６ indicates that the number of carbon atoms is 2 to 6.

[0064] Examples of halogen include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. In this specification, the term "halo" also refers to these halogens. Examples of alkyl include methyl, ethyl, propyl, i-propyl, butyl, i-butyl, t-butyl, s-butyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1-ethylpropyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, neopentyl, hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1-ethylbutyl, 2-ethylbutyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1,1,2-trimethylpropyl, 1-ethyl-1-methylpropyl, 1-ethyl-2-methylpropyl, and the like, and each alkyl group is selected within the range of the specified number of carbon atoms.

[0065] Haloalkyl means an alkyl group substituted with one or more halogen atoms, and examples of haloalkyl include fluoromethyl, chloromethyl, bromomethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 3-fluoropropyl, 3-chloropropyl, difluoromethyl, chlorodifluoromethyl, trifluoromethyl, dichloromethyl, trichloromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2,2,2-trichloroethyl, chlorodifluoromethyl, bromodifluoromethyl, pentafluoroethyl, heptafluoropropyl, heptafluoroisopropyl, 4-chlorobutyl, 4-fluorobutyl, and the like, each of which is selected from the range of carbon atoms specified.

[0066] Fluoroalkyl means an alkyl group substituted with one or more fluorine atoms, and examples of fluoroalkyl include fluoromethyl, 2-fluoroethyl, 3-fluoropropyl, difluoromethyl, trifluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, pentafluoroethyl, heptafluoropropyl, heptafluoroisopropyl, 4-fluorobutyl, and the like, each selected from the range of carbon numbers specified.

[0067] Examples of alkenyl include ethenyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-2-propenyl, 1-hexenyl, 1,1-dimethyl-2-butenyl, 1,2-dimethyl-2-butenyl, 1,3-dimethyl-2-butenyl, 2,3-dimethyl-2-butenyl, 1-ethyl-2-butenyl, 2-ethyl-2-butenyl, 1,1,2-trimethyl-2-propenyl, and 1-ethyl-1-methyl-2-propenyl, each of which is selected from the range of carbon atoms specified for that group.

[0068] Haloalkenyl includes 1-chloroethenyl, 2-chloroethenyl, 2-fluoroethenyl, 2,2-dichloroethenyl, 3-chloro-2-propenyl, 3-fluoro-2-propenyl, 2-chloro-2-propenyl, 4-chloro-3-butenyl, and the like, each selected from the range of carbon numbers specified.

[0069] Examples of alkynyl include ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 1-methyl-2-butynyl, 2-methyl-3-butynyl, 1-hexynyl, 1-methyl-3-pentynyl, 2-methyl-3-pentynyl, 3-methyl-4-pentynyl, 4-methyl-2-pentynyl, 1,1-dimethyl-2-butynyl, 1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 1-ethyl-2-butynyl, and 2-ethyl-3-butynyl, each of which is selected from the range of carbon atoms specified for that group.

[0070] Haloalkynyl includes chloroethynyl, fluoroethynyl, bromoethynyl, 3-chloro-2-propynyl, 4-chloro-2-butynyl, and the like, each selected from the range of carbon numbers specified.

[0071] Cycloalkyl includes cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc., each selected from the range of carbon numbers specified.

[0072] Halocycloalkyl includes 2-fluorocyclopropyl, 1-chlorocyclopropyl, 2-bromo-1-methylcyclopropyl, 2,2-difluorocyclopropyl, 1,2-dichlorocyclopropyl, and the like, each selected from the range of carbon numbers specified.

[0073] Examples of cycloalkylalkyl include cyclopropylmethyl, 2-cyclopropylethyl, cyclopentylmethyl, cyclohexylmethyl, and the like, each selected from the range of carbon numbers specified.

[0074] Phenylalkyl and Z ２ Examples of the phenylalkyl substituted by one or more substituents selected from the above include benzyl, 2-fluorobenzyl, 3-fluorobenzyl, 4-fluorobenzyl, 2-chlorobenzyl, 3-bromobenzyl, 4-iodobenzyl, 2,4-difluorobenzyl, 2-methylbenzyl, 3-methylbenzyl, 4-methylbenzyl, 2-methoxybenzyl, 4-methoxybenzyl, 4-aminobenzyl, 4-trifluoromethoxybenzyl, 2-methylthiobenzyl, 3-trifluoromethylthiobenzyl, 2-cyanobenzyl, 4-nitrobenzyl, 2-trifluoromethylbenzyl, 2-phenethyl, and the like, and each is selected from the range of carbon atoms specified for that group.

[0075] Heterocyclylalkyl and Z ２ Heterocyclyl C substituted by one or more substituents selected from １ ~C ６Examples of alkyl include (oxiran-2-yl)methyl, (2-methyloxiran-2-yl)methyl, (3,3-dimethyloxiran-2-yl)methyl, (oxetan-2-yl)methyl, (oxetan-3-yl)methyl, (tetrahydrofuran-2-yl)methyl, (tetrahydrofuran-3-yl)methyl, (tetrahydrofuran-4-yl)methyl, (tetrahydrothiophen-2-yl)methyl, and (1,1-dioxytetrahydrothiophen-2-yl). (1-(pyridin-4-yl)ethyl, 2-(1,3-dioxan-2-yl)ethyl, (thiophen-2-yl)methyl, (thiophen-3-yl)methyl, (pyridin-2-yl)methyl, (pyridin-3-yl)methyl, (pyridin-4-yl)methyl, 1-(pyridin-4-yl)ethyl, 2-(pyridin-4-yl)ethyl, and the like, and each is selected from the range of the number of carbon atoms specified for each.

[0076] Cyanoalkyl includes cyanomethyl, 1-cyanoethyl, 2-cyanoethyl, etc., each selected from the range of carbon numbers specified.

[0077] Examples of alkoxyalkyl include methoxymethyl, ethoxymethyl, propyloxymethyl, i-propyloxymethyl, butyloxymethyl, i-butyloxymethyl, s-butyloxymethyl, t-butyloxymethyl, pentyloxymethyl, 1-methoxyethyl, 2-methoxyethyl, 2-ethoxyethyl, and 3-methoxypropyl, each of which is selected from the specified range of carbon numbers.

[0078] Haloalkoxyalkyl includes fluoromethoxymethyl, chloromethoxymethyl, bromomethoxymethyl, 2,2,2-trifluoroethoxymethyl, 2-(chloromethoxy)ethyl, and the like, each selected from the range of carbon numbers specified.

[0079] Examples of cycloalkyloxyalkyl include cyclopropyloxymethyl, 2-cyclopropyloxyethyl, cyclopentyloxymethyl, cyclohexyloxymethyl, and the like, each selected from the range of carbon numbers specified.

[0080] Phenoxyalkyl and Z ２ Examples of the phenoxyalkyl substituted by one or more substituents selected from include phenoxymethyl, 2-fluorophenoxymethyl, 2-chlorophenoxymethyl, 3-bromophenoxymethyl, 4-iodophenoxymethyl, 4-methylphenoxymethyl, 2-methoxyphenoxymethyl, 4-aminophenoxymethyl, 4-trifluoromethoxyphenoxymethyl, 2-methylthiophenoxymethyl, 3-trifluoromethylthiophenoxymethyl, 2-cyanophenoxymethyl, 4-nitrophenoxymethyl, 2-trifluoromethylphenoxymethyl, 2-(phenoxy)ethyl, and the like, each selected from the range of carbon numbers specified for that group.

[0081] Phenylalkoxyalkyl and Z ２ Examples of the phenylalkoxyalkyl substituted by one or more substituents selected from the above include benzyloxymethyl, 2-fluorobenzyloxymethyl, 2-chlorobenzyloxymethyl, 3-bromobenzyloxymethyl, 4-iodobenzyloxymethyl, 4-methylbenzyloxymethyl, 2-methoxybenzyloxymethyl, 4-aminobenzyloxymethyl, 4-trifluoromethoxybenzyloxymethyl, 2-methylthiobenzyloxymethyl, 3-trifluoromethylthiobenzyloxymethyl, 2-cyanobenzyloxymethyl, 4-nitrobenzyloxymethyl, 2-trifluoromethylbenzyloxymethyl, 2-phenethyloxymethyl, 1-(benzyloxy)ethyl, 2-(benzyloxy)ethyl, and the like, and each is selected from the range of carbon atoms specified for that group.

[0082] Examples of trialkylsilylalkoxyalkyl include trimethylsilylmethoxymethyl, 2-(trimethylsilyl)ethoxymethyl, 2-(trimethylsilylmethoxy)ethyl, and 2-[2-(trimethylsilyl)ethoxy]ethyl, each of which is selected from the range of the specified number of carbon atoms.

[0083] Phenylcarbonyloxyalkyl and Z ２Examples of the phenylcarbonyloxyalkyl substituted by one or more substituents selected from the above include phenylcarbonyloxymethyl, 2-fluorophenylcarbonyloxymethyl, 2-chlorophenylcarbonyloxymethyl, 3-bromophenylcarbonyloxymethyl, 4-iodophenylcarbonyloxymethyl, 4-methylphenylcarbonyloxymethyl, 2-methoxyphenylcarbonyloxymethyl, 4-aminophenylcarbonyloxymethyl, 4-trifluoromethoxyphenylcarbonyloxymethyl, 2-methylthiophenylcarbonyloxymethyl, 3-trifluoromethylthiophenylcarbonyloxymethyl, 2-cyanophenylcarbonyloxymethyl, 4-nitrophenylcarbonyloxymethyl, 2-trifluoromethylphenylcarbonyloxymethyl, 2-(phenylcarbonyloxy)ethyl, and the like, and each is selected from the range of carbon numbers specified for each.

[0084] Heterocyclylcarbonyloxyalkyl and Z ２ Examples of the heterocyclylcarbonyloxyalkyl substituted by one or more substituents selected from include (tetrahydrofuran-2-yl)carbonyloxymethyl, (tetrahydrofuran-3-yl)carbonyloxymethyl, (tetrahydrothiophen-2-yl)carbonyloxymethyl, (tetrahydropyran-4-yl)carbonyloxymethyl, (furan-2-yl)carbonyloxymethyl, (3-methylfuran-2-yl)carbonyloxymethyl, (furan-3-yl)carbonyloxymethyl, (thiophen-2-yl)carbonyloxymethyl, (thiophen-3-yl)carbonyloxymethyl, (pyridin-2-yl)carbonyloxymethyl, (pyridin-3-yl)carbonyloxymethyl, (pyridin-4-yl)carbonyloxymethyl, and the like, and each is selected from the range of the number of carbon atoms specified.

[0085] Examples of the alkoxyalkoxyalkyl include methoxymethoxymethyl, ethoxymethoxymethyl, propyloxymethoxymethyl, i-propoxymethoxymethyl, butyloxymethoxymethyl, 1-(methoxymethoxy)ethyl, 2-(methoxymethoxy)ethyl, 2-(ethoxymethoxy)ethyl, 2-(ethoxy)ethoxymethyl, and the like, each selected from the range of the specified number of carbon atoms.

[0086] Examples of haloalkoxyalkoxyalkyl include fluoromethoxymethoxymethyl, chloromethoxymethoxymethyl, bromomethoxymethoxymethyl, 2,2,2-trifluoroethoxymethoxymethyl, 2-(chloromethoxymethoxy)ethyl, and the like, each selected from the range of carbon numbers specified.

[0087] Phenylcarbonyloxyalkoxyalkyl and Z ２ Examples of the phenylcarbonyloxyalkoxyalkyl substituted by one or more substituents selected from the above include phenylcarbonyloxymethoxymethyl, 2-fluorophenylcarbonyloxymethoxymethyl, 2-chlorophenylcarbonyloxymethoxymethyl, 3-bromophenylcarbonyloxymethoxymethyl, 4-iodophenylcarbonyloxymethoxymethyl, 4-methylphenylcarbonyloxymethoxymethyl, 2-methoxyphenylcarbonyloxymethoxymethyl, 4-aminophenylcarbonyloxymethoxymethyl, 4-trifluoromethoxyphenylcarbonyloxymethoxymethyl, 2-methylthiophenylcarbonyloxymethoxymethyl, 3-trifluoromethylthiophenylcarbonyloxymethoxymethyl, 2-cyanophenylcarbonyloxymethoxymethyl, 4-nitrophenylcarbonyloxymethoxymethyl, 2-trifluoromethylphenylcarbonyloxymethoxymethyl, 2-(phenylcarbonyloxy)ethoxymethyl, 2-(phenylcarbonyloxymethoxy)ethyl, and the like.

[0088] Examples of alkylcarbonyloxyalkyl include acetoxymethyl, propionyloxymethyl, butyryloxymethyl, i-butyryloxymethyl, valeroyloxymethyl, i-valeroyloxymethyl, 2-methylbutyryloxymethyl, pivaloyloxymethyl, heptanoyloxymethyl, 1-(acetoxy)ethyl, 2-(acetoxy)ethyl, 2-(propionyloxy)ethyl, and 3-(acetoxy)propyl, each of which is selected from the range of carbon atoms specified for that group.

[0089] Examples of haloalkylcarbonyloxyalkyl include fluoromethylcarbonyloxymethyl, chloromethylcarbonyloxymethyl, bromomethylcarbonyloxymethyl, 2,2,2-trifluoroethylcarbonyloxymethyl, 2-(chloromethylcarbonyloxy)ethyl, and the like, each selected from the range of carbon numbers specified.

[0090] Examples of cycloalkylcarbonyloxyalkyl include cyclopropanecarbonyloxymethyl, cyclobutanecarbonyloxymethyl, cyclopentanecarbonyloxymethyl, 2-(cyclohexanecarbonyloxy)ethyl, and the like, each selected from the range of carbon numbers specified.

[0091] Examples of the alkoxycarbonyloxyalkyl include methoxycarbonyloxymethyl, ethoxycarbonyloxymethyl, propyloxycarbonyloxymethyl, i-propyloxycarbonyloxymethyl, butyloxycarbonyloxymethyl, 2-methoxycarbonyloxyethyl, 2-(ethoxycarbonyloxy)ethyl, 3-(methoxycarbonyloxy)propyl, and the like, and each is selected from the range of carbon numbers specified.

[0092] Phenoxycarbonyloxyalkyl and Z ２Examples of the phenoxycarbonyloxyalkyl substituted by one or more substituents selected from include phenoxycarbonyloxymethyl, 1-(phenoxycarbonyloxy)ethyl, 2-(phenoxycarbonyloxy)ethyl, 2-fluorophenoxycarbonyloxymethyl, 2-chlorophenoxycarbonyloxymethyl, 4-bromophenoxycarbonyloxymethyl, 4-methylphenoxycarbonyloxymethyl, 2-methoxyphenoxycarbonyloxymethyl, 3-aminophenoxycarbonyloxymethyl, 4-trifluoromethoxyphenoxycarbonyloxymethyl, 2-methylthiophenoxycarbonyloxymethyl, 3-trifluoromethylthiophenoxycarbonyloxymethyl, 4-cyanophenoxycarbonyloxymethyl, 2-nitrophenoxycarbonyloxymethyl, 2-(4-trifluoromethylphenoxycarbonyloxy)ethyl, and the like, each of which is selected from the range of carbon numbers specified for that group.

[0093] Examples of the monoalkylaminocarbonyloxyalkyl include methylaminocarbonyloxymethyl, ethylaminocarbonyloxymethyl, propylaminocarbonyloxymethyl, i-propylaminocarbonyloxymethyl, butylaminocarbonyloxymethyl, 2-(methylaminocarbonyloxy)ethyl, 2-(ethylaminocarbonyloxy)ethyl, 3-(methylaminocarbonyloxy)propyl, and the like, each of which is selected from the range of carbon numbers specified for that group.

[0094] Examples of dialkylaminocarbonyloxyalkyl include dimethylaminocarbonyloxymethyl, diethylaminocarbonyloxymethyl, ethyl(methyl)aminocarbonyloxymethyl, methyl(propyl)aminocarbonyloxymethyl, butyl(methyl)aminocarbonyloxymethyl, 2-(diethylaminocarbonyloxy)ethyl, 2-{ethyl(methyl)aminocarbonyloxy}propyl, and the like, each of which is selected from the range of carbon numbers specified for that group.

[0095] Phenylaminocarbonyloxyalkyl and Z ２Examples of the phenylaminocarbonyloxyalkyl substituted by one or more substituents selected from the above include phenylaminocarbonyloxymethyl, 2-fluorophenylaminocarbonyloxymethyl, 2-chlorophenylaminocarbonyloxymethyl, 3-bromophenylaminocarbonyloxymethyl, 4-iodophenylaminocarbonyloxymethyl, 4-methylphenylaminocarbonyloxymethyl, 2-methoxyphenylaminocarbonyloxymethyl, 4-aminophenylaminocarbonyloxymethyl, 4-trifluoromethoxyphenylaminocarbonyloxymethyl, 2-methylthiophenylaminocarbonyloxymethyl, 3-trifluoromethylphenylaminocarbonyloxymethyl, 2-cyanophenylaminocarbonyloxymethyl, 4-nitrophenylaminocarbonyloxymethyl, 2-trifluoromethylphenylaminocarbonyloxymethyl, 2-(phenylaminocarbonyloxy)ethyl, and the like, and each is selected from the range of the specified number of carbon atoms.

[0096] Alkyl(phenyl)aminocarbonyloxyalkyl and alkyl(Z ２Examples of the (phenyl)aminocarbonyloxyalkyl alkyl substituted by one or more substituents selected from the above include methyl(phenyl)aminocarbonyloxymethyl, methyl(2-fluorophenyl)aminocarbonyloxymethyl, methyl(2-chlorophenyl)aminocarbonyloxymethyl, methyl(3-bromophenyl)aminocarbonyloxymethyl, methyl(4-iodophenyl)aminocarbonyloxymethyl, methyl(4-methylphenyl)aminocarbonyloxymethyl, methyl(2-methoxyphenyl)aminocarbonyloxymethyl, methyl(4-aminophenyl)aminocarbonyloxymethyl, methyl(4-trifluoromethoxy)phenylaminocarbonyloxymethyl, methyl(2-methylthiophenyl)aminocarbonyloxymethyl, methyl(3-trifluoromethylphenyl)aminocarbonyloxymethyl, methyl(2-cyanophenyl)aminocarbonyloxymethyl, methyl(4-nitrophenyl)aminocarbonyloxymethyl, ethyl(phenyl)aminocarbonyloxymethyl, 2-{methyl(phenyl)aminocarbonyloxy}ethyl, and the like, and each may be selected from the range of the specified number of carbon atoms.

[0097] Examples of alkylthioalkyl include methylthiomethyl, ethylthiomethyl, propylthiomethyl, i-propylthiomethyl, butylthiomethyl, i-butylthiomethyl, s-butylthiomethyl, t-butylthiomethyl, pentylthiomethyl, 1-methylthioethyl, 2-methylthioethyl, 2-ethylthioethyl, and 3-methylthiopropyl, each of which is selected from the range of carbon atoms specified for that group.

[0098] Haloalkylthioalkyl includes fluoromethylthiomethyl, chloromethylthiomethyl, bromomethylthiomethyl, 2,2,2-trifluoroethylthiomethyl, 2-(chloromethylthio)ethyl, etc., each selected from the range of carbon numbers specified. Alkylsulfinyl includes methylsulfinyl, ethylsulfinyl, propylsulfinyl, i-propylsulfinyl, butylsulfinyl, i-butylsulfinyl, s-butylsulfinyl, t-butylsulfinyl, etc., each selected from the range of carbon numbers specified.

[0099] Examples of alkylsulfinylalkyl include methylsulfinylmethyl, ethylsulfinylmethyl, propylsulfinylmethyl, i-propylsulfinylmethyl, butylsulfinylmethyl, i-butylsulfinylmethyl, s-butylsulfinylmethyl, t-butylsulfinylmethyl, pentylsulfinylmethyl, 1-(methylsulfinyl)ethyl, 2-(methylsulfinyl)ethyl, 2-(ethylsulfinyl)ethyl, 3-(methylsulfinyl)propyl, and the like, each of which is selected from the range of carbon atoms specified for that group.

[0100] Examples of haloalkylsulfinylalkyl include fluoromethylsulfinylmethyl, chloromethylsulfinylmethyl, bromomethylsulfinylmethyl, 2,2,2-trifluoroethylsulfinylmethyl, 2-(chloromethylsulfinyl)ethyl, and the like, each selected from the range of carbon numbers specified.

[0101] Examples of alkylsulfonylalkyl include methylsulfonylmethyl, ethylsulfonylmethyl, propylsulfonylmethyl, i-propylsulfonylmethyl, butylsulfonylmethyl, i-butylsulfonylmethyl, s-butylsulfonylmethyl, t-butylsulfonylmethyl, pentylsulfonylmethyl, 1-(methylsulfonyl)ethyl, 2-(methylsulfonyl)ethyl, 2-(ethylsulfonyl)ethyl, 3-(methylsulfonyl)propyl, and the like, each of which is selected from the range of carbon atoms specified for that group.

[0102] Examples of haloalkylsulfonylalkyl include fluoromethylsulfonylmethyl, chloromethylsulfonylmethyl, bromomethylsulfonylmethyl, 2,2,2-trifluoroethylsulfonylmethyl, 2-(chloromethylsulfonyl)ethyl, and the like, each selected from the range of carbon numbers specified.

[0103] Phenylthioalkyl and Z ２Examples of the phenylthioalkyl substituted by one or more substituents selected from the above include phenylthiomethyl, 2-fluorophenylthiomethyl, 2-chlorophenylthiomethyl, 3-bromophenylthiomethyl, 4-iodophenylthiomethyl, 4-methylphenylthiomethyl, 2-methoxyphenylthiomethyl, 4-aminophenylthiomethyl, 4-trifluoromethoxyphenylthiomethyl, 2-methylthiophenylthiomethyl, 3-trifluoromethylthiophenylthiomethyl, 2-cyanophenylthiomethyl, 4-nitrophenylthiomethyl, 2-trifluoromethylphenylthiomethyl, 2-(phenylthio)ethyl, and the like, and each is selected from the range of carbon numbers specified.

[0104] Phenylsulfinylalkyl and Z ２ Examples of the phenylsulfinylalkyl substituted by one or more substituents selected from include phenylsulfinylmethyl, 2-fluorophenylsulfinylmethyl, 2-chlorophenylsulfinylmethyl, 3-bromophenylsulfinylmethyl, 4-iodophenylsulfinylmethyl, 4-methylphenylsulfinylmethyl, 2-methoxyphenylsulfinylmethyl, 4-aminophenylsulfinylmethyl, 4-trifluoromethoxyphenylsulfinylmethyl, 2-methylthiophenylsulfinylmethyl, 3-trifluoromethylthiophenylsulfinylmethyl, 2-cyanophenylsulfinylmethyl, 4-nitrophenylsulfinylmethyl, 2-trifluoromethylphenylsulfinylmethyl, 2-(phenylsulfinyl)ethyl, and the like, and each is selected from the range of the number of carbon atoms specified.

[0105] Phenylsulfonylalkyl and Z ２Examples of the phenylsulfonylalkyl substituted by one or more substituents selected from include phenylsulfonylmethyl, 2-fluorophenylsulfonylmethyl, 2-chlorophenylsulfonylmethyl, 3-bromophenylsulfonylmethyl, 4-iodophenylsulfonylmethyl, 4-methylphenylsulfonylmethyl, 2-methoxyphenylsulfonylmethyl, 4-aminophenylsulfonylmethyl, 4-trifluoromethoxyphenylsulfonylmethyl, 2-methylthiophenylsulfonylmethyl, 3-trifluoromethylthiophenylsulfonylmethyl, 2-cyanophenylsulfonylmethyl, 4-nitrophenylsulfonylmethyl, 2-trifluoromethylphenylsulfonylmethyl, 2-(phenylsulfonyl)ethyl, and the like, and each is selected from the range of carbon numbers specified for each.

[0106] Phenylalkylthioalkyl and Z ２ Examples of the phenylalkylthioalkyl substituted by one or more substituents selected from the above include benzylthiomethyl, 2-fluorobenzylthiomethyl, 2-chlorobenzylthiomethyl, 3-bromobenzylthiomethyl, 4-iodobenzylthiomethyl, 4-methylbenzylthiomethyl, 2-methoxybenzylthiomethyl, 4-aminobenzylthiomethyl, 4-trifluoromethoxybenzylthiomethyl, 2-methylthiobenzylthiomethyl, 3-trifluoromethylthiobenzylthiomethyl, 2-cyanobenzylthiomethyl, 4-nitrobenzylthiomethyl, 2-trifluoromethylbenzylthiomethyl, phenethylthiomethyl, 2-(benzylthio)ethyl, and the like, and each is selected from the range of carbon numbers specified for that group.

[0107] Phenylalkylsulfinylalkyl and Z ２Examples of the phenylalkylsulfinylalkyl substituted by one or more substituents selected from the above include benzylsulfinylmethyl, 2-fluorobenzylsulfinylmethyl, 2-chlorobenzylsulfinylmethyl, 3-bromobenzylsulfinylmethyl, 4-iodobenzylsulfinylmethyl, 4-methylbenzylsulfinylmethyl, 2-methoxybenzylsulfinylmethyl, 4-aminobenzylsulfinylmethyl, 4-trifluoromethoxybenzylsulfinylmethyl, 2-methylthiobenzylsulfinylmethyl, 3-trifluoromethylsulfinylbenzylthiomethyl, 2-cyanobenzylsulfinylmethyl, 4-nitrobenzylsulfinylmethyl, 2-trifluoromethylbenzylsulfinylmethyl, phenethylsulfinylmethyl, 2-(benzylsulfinyl)ethyl, and the like, and each is selected from the range of the specified number of carbon atoms.

[0108] Phenylalkylsulfonylalkyl and Z ２ Examples of the phenylalkylsulfonylalkyl substituted by one or more substituents selected from the above include benzylsulfonylmethyl, 2-fluorobenzylsulfonylmethyl, 2-chlorobenzylsulfonylmethyl, 3-bromobenzylsulfonylmethyl, 4-iodobenzylsulfonylmethyl, 4-methylbenzylsulfonylmethyl, 2-methoxybenzylsulfonylmethyl, 4-aminobenzylsulfonylmethyl, 4-trifluoromethoxybenzylsulfonylmethyl, 2-methylthiobenzylsulfonylmethyl, 3-trifluoromethylthiobenzylsulfonylmethyl, 2-cyanobenzylsulfonylmethyl, 4-nitrobenzylsulfonylmethyl, 2-trifluoromethylbenzylsulfonylmethyl, phenethylsulfonylmethyl, 2-(benzylsulfonyl)ethyl, and the like, and each is selected from the range of carbon numbers specified for each.

[0109] The thiocyanatoalkyl includes cyanothiomethyl, 1-(cyanothio)ethyl, 1-(cyanothio)ethyl, and the like, each selected from the range of carbon numbers specified.

[0110] Examples of alkylcarbonylalkyl include methylcarbonylmethyl, ethylcarbonylmethyl, propylcarbonylmethyl, i-propylcarbonylmethyl, butylcarbonylmethyl, i-butylcarbonylmethyl, s-butylcarbonylmethyl, t-butylcarbonylmethyl, pentylcarbonylmethyl, 1-(methylcarbonyl)ethyl, 2-(methylcarbonyl)ethyl, 2-(ethylcarbonyl)ethyl, and 3-(methylcarbonyl)propyl, each of which is selected from the range of carbon numbers specified for that group.

[0111] Examples of haloalkylcarbonylalkyl include fluoromethylcarbonylmethyl, chloromethylcarbonylmethyl, bromomethylcarbonylmethyl, 2,2,2-trifluoroethylcarbonylmethyl, 2-(chloromethylcarbonyl)ethyl, and the like, each selected from the range of the specified number of carbon atoms.

[0112] Examples of the alkoxycarbonylalkyl include methoxycarbonylmethyl, ethoxycarbonylmethyl, propyloxycarbonylmethyl, i-propyloxycarbonylmethyl, butyloxycarbonylmethyl, 2-(methoxycarbonyl)ethyl, 2-(ethoxycarbonyl)ethyl, 3-(methoxycarbonyl)propyl, and the like, each of which is selected from the range of carbon numbers specified.

[0113] Examples of haloalkoxycarbonylalkyl include fluoromethoxycarbonylmethyl, chloromethoxycarbonylmethyl, bromomethoxycarbonylmethyl, 2,2,2-trifluoroethoxycarbonylmethyl, 2-(chloromethoxycarbonyl)ethyl, and the like, each selected from the range of the specified number of carbon atoms.

[0114] Phenylcarbonylalkyl and Z ２Examples of the phenylcarbonylalkyl substituted by one or more substituents selected from include phenylcarbonylmethyl, 2-fluorophenylcarbonylmethyl, 2-chlorophenylcarbonylmethyl, 3-bromophenylcarbonylmethyl, 4-iodophenylcarbonylmethyl, 4-methylphenylcarbonylmethyl, 2-methoxyphenylcarbonylmethyl, 4-aminophenylcarbonylmethyl, 4-trifluoromethoxyphenylcarbonylmethyl, 2-methylthiophenylcarbonylmethyl, 3-trifluoromethylthiophenylcarbonylmethyl, 2-cyanophenylcarbonylmethyl, 4-nitrophenylcarbonylmethyl, 2-trifluoromethylphenylcarbonylmethyl, 2-phenylcarbonylethyl, and the like, each selected from the range of carbon numbers specified for that group.

[0115] Examples of alkylcarbonyl include acetyl, ethylcarbonyl, propionyl, butyryl, i-butyryl, valeroyl, i-valeroyl, 2-methylbutyryl, pivaloyl, hexanoyl, 2-ethylbutyryl, 2,2-dimethyl-1-propionyl, 2-methylvaleroyl, 4-methylvaleroyl, heptanoyl, 2,2-dimethylvaleroyl, 2-ethylhexanoyl, 2-propylvaleroyl, octanoyl, nonanoyl, 3,5,5-trimethylhexanoyl, and decanoyl, each of which is selected from the range of carbon numbers specified.

[0116] Examples of haloalkylcarbonyl include fluoroacetyl, chloroacetyl, difluoroacetyl, dichloroacetyl, trifluoroacetyl, chlorodifluoroacetyl, bromodifluoroacetyl, trichloroacetyl, pentafluoropropionyl, 4-chlorobutyryl, heptafluorobutyryl, and 3-chloro-2,2-dimethylpropionyl, and each is selected from the range of carbon atoms specified.

[0117] Examples of cycloalkylcarbonyl include cyclopropanecarbonyl, cyclobutanecarbonyl, cyclopentanecarbonyl, cyclohexanecarbonyl, and the like, each selected from the range of carbon numbers specified for that group.

[0118] Examples of halocycloalkylcarbonyl include 2-fluorocyclopropanecarbonyl, 1-chlorocyclopropanecarbonyl, 2-bromo-1-methylcyclopropanecarbonyl, 2,2-difluorocyclopropanecarbonyl, 1,2-dichlorocyclopropanecarbonyl, and the like, each selected from the range of carbon numbers specified.

[0119] Examples of the alkylcycloalkylcarbonyl include 2-methylcyclopropanecarbonyl, 2,2-dimethylcyclopropanecarbonyl, 2,2,4,4-tetramethylcyclobutanecarbonyl, 4-(i-propyl)cyclohexanecarbonyl, and the like, each selected from the range of carbon numbers specified.

[0120] Examples of the alkylhalocycloalkylcarbonyl include 2-chloro-3-methylcyclopropanecarbonyl, 2,2-dichloro-1-methylcyclopropanecarbonyl, 3-fluoro-4-(i-propyl)cyclohexanecarbonyl, and the like, each selected from the range of carbon numbers specified.

[0121] Examples of alkenylcarbonyl include ethenylcarbonyl, 1-methylethenylcarbonyl, 1-propenylcarbonyl, 2-propenylcarbonyl, 1-butenylcarbonyl, 1-methyl-2-propenylcarbonyl, 2-methyl-1-propenylcarbonyl, 2-methyl-2-propenylcarbonyl, and 1-hexenylcarbonyl, and each is selected from the range of carbon numbers specified.

[0122] Examples of haloalkenylcarbonyl include 1-chloroethenylcarbonyl, 2-chloroethenylcarbonyl, 2-fluoroethenylcarbonyl, 2,2-dichloroethenylcarbonyl, 3-chloro-2-propenylcarbonyl, 3-fluoro-2-propenylcarbonyl, 2-chloro-2-propenylcarbonyl, and 4-chloro-3-butenylcarbonyl, and each is selected from the range of carbon numbers specified.

[0123] Phenylalkenylcarbonyl and Z ２Examples of the phenylalkenylcarbonyl substituted by one or more substituents selected from include 1-phenylethenylcarbonyl, 2-phenylethenylcarbonyl, 3-phenyl-2-propenylcarbonyl, 4-phenyl-3-butenylcarbonyl, and the like, each selected from the range of carbon numbers specified for that group.

[0124] Examples of the alkoxyalkenylcarbonyl include 1-methoxyethenylcarbonyl, 1-ethoxyethenylcarbonyl, 1-(i-propyloxy)ethenylcarbonyl, 2-methoxyethenylcarbonyl, 2-ethoxyethenylcarbonyl, 3-methoxy-2-propenylcarbonyl, and 4-methoxy-3-butenylcarbonyl, and each is selected from the range of carbon numbers specified.

[0125] Examples of alkynylcarbonyl include ethynylcarbonyl, 1-propynylcarbonyl, 2-propynylcarbonyl, 1-butynylcarbonyl, 2-butynylcarbonyl, 3-butynylcarbonyl, 1-methyl-2-propynylcarbonyl, 1-pentynylcarbonyl, 1-methyl-2-butynylcarbonyl, 2-methyl-3-butynylcarbonyl, 1-hexynylcarbonyl, and 1-methyl-3-pentynylcarbonyl. Examples include 2-methyl-3-pentynylcarbonyl, 3-methyl-4-pentynylcarbonyl, 4-methyl-2-pentynylcarbonyl, 1,1-dimethyl-2-butynylcarbonyl, 1,2-dimethyl-3-butynylcarbonyl, 2,2-dimethyl-3-butynylcarbonyl, 1-ethyl-2-butynylcarbonyl, and 2-ethyl-3-butynylcarbonyl, and the like, each of which is selected from the range of carbon numbers specified for each.

[0126] Z ２Examples of the phenylcarbonyl substituted by one or more substituents selected from the above include 2-fluorophenylcarbonyl, 2-chlorophenylcarbonyl, 4-bromophenylcarbonyl, 4-methylphenylcarbonyl, 2-methoxyphenylcarbonyl, 3-aminophenylcarbonyl, 4-trifluoromethoxyphenylcarbonyl, 2-methylthiophenylcarbonyl, 3-trifluoromethylthiophenylcarbonyl, 4-cyanophenylcarbonyl, 2-nitrophenylcarbonyl, and 4-trifluoromethylphenylcarbonyl.

[0127] Heterocyclylcarbonyl and Z ２ Examples of the heterocyclylcarbonyl substituted by one or more substituents selected from include (tetrahydrofuran-2-yl)carbonyl, (tetrahydrofuran-3-yl)carbonyl, (tetrahydrothiophen-2-yl)carbonyl, (tetrahydropyran-4-yl)carbonyl, (furan-2-yl)carbonyl, (3-methylfuran-2-yl)carbonyl, (furan-3-yl)carbonyl, (thiophen-2-yl)carbonyl, (thiophen-3-yl)carbonyl, (pyridin-2-yl)carbonyl, (N-methylpyrrol-2-yl)carbonyl, (pyridin-3-yl)carbonyl, (pyridin-4-yl)carbonyl, and the like, each of which is selected from the range of carbon numbers specified.

[0128] Examples of the cycloalkylalkylcarbonyl include cyclopropylmethylcarbonyl, 2-cyclopropylethylcarbonyl, cyclopentylmethylcarbonyl, cyclohexylmethylcarbonyl, and the like, each selected from the range of carbon numbers specified.

[0129] Phenylalkylcarbonyl and Z ２Examples of the phenylalkylcarbonyl substituted by one or more substituents selected from the above include benzylcarbonyl, 2-fluorobenzylcarbonyl, 3-fluorobenzylcarbonyl, 4-fluorobenzylcarbonyl, 2-chlorobenzylcarbonyl, 3-bromobenzylcarbonyl, 4-iodobenzylcarbonyl, 2,4-difluorobenzylcarbonyl, 2-methylbenzylcarbonyl, 3-methylbenzylcarbonyl, 4-methylbenzylcarbonyl, 2-methoxybenzylcarbonyl, 4-aminobenzylcarbonyl, 4-trifluoromethoxybenzylcarbonyl, 2-methylthiobenzylcarbonyl, 3-trifluoromethylthiobenzylcarbonyl, 2-cyanobenzylcarbonyl, 4-nitrobenzylcarbonyl, 2-trifluoromethylbenzylcarbonyl, 2-phenethylcarbonyl, and the like, and each is selected from the range of carbon numbers specified for that group.

[0130] Heterocyclylalkylcarbonyl and Z ２ The heterocyclylalkylcarbonyl substituted by one or more substituents selected from the group consisting of (oxiran-2-yl)methylcarbonyl, (2-methyloxiran-2-yl)methylcarbonyl, (3,3-dimethyloxiran-2-yl)methylcarbonyl, (oxetan-2-yl)methylcarbonyl, (oxetan-3-yl)methylcarbonyl, 2-tetrahydrofurfurylcarbonyl, 3-tetrahydrofurfurylcarbonyl, (tetrahydrothiophen-2-yl)methylcarbonyl, ( Examples include (1,1-dioxytetrahydrothiophen-2-yl)methylcarbonyl, (tetrahydropyran-4-yl)methylcarbonyl, (1,3-dioxan-2-yl)methylcarbonyl, 2-furfuryl, 3-furfuryl, (thiophen-2-yl)methylcarbonyl, (thiophen-3-yl)methylcarbonyl, (pyridin-2-yl)methylcarbonyl, (pyridin-3-yl)methylcarbonyl, (pyridin-4-yl)oxycarbonyl, and the like, and each is selected from the range of the number of carbon atoms specified.

[0131] Examples of the hydroxyalkylcarbonyl include hydroxyacetyl, 2-hydroxyethylcarbonyl, 3-hydroxypropionyl, 3-hydroxybutyryl, 2-hydroxy-i-butyryl, 5-hydroxyvaleroyl, 3-hydroxy-i-valeroyl, 5-hydroxy-2-methylbutyryl, 2-hydroxypivaloyl, 6-hydroxyhexanoyl, and 5-hydroxy-2,2-dimethylvaleroyl, and each is selected from the range of carbon numbers specified.

[0132] Examples of the alkoxyalkylcarbonyl include methoxymethylcarbonyl, ethoxymethylcarbonyl, i-propyloxymethylcarbonyl, 2-methoxyethylcarbonyl, 3-methoxybutyryl, 2-methoxy-i-butyryl, 5-ethoxyvaleroyl, and 5-methoxy-2,2-dimethylvaleroyl, and each is selected from the range of carbon numbers specified.

[0133] Examples of haloalkoxyalkylcarbonyl include fluoromethoxyacetyl, chloromethoxyacetyl, bromomethoxyacetyl, 2,2,2-trifluoroethoxyacetyl, 2-(chloromethoxycarbonyl)ethylcarbonyl, and the like, each selected from the range of carbon numbers specified.

[0134] Phenoxyalkylcarbonyl and Z ２ Examples of the phenoxyalkylcarbonyl substituted by one or more substituents selected from the above include phenoxymethylcarbonyl, 2-phenoxyethylcarbonyl, 2-fluorophenoxymethylcarbonyl, 2-chlorophenoxymethylcarbonyl, 4-bromophenoxymethylcarbonyl, 4-methylphenoxymethylcarbonyl, 2-methoxyphenoxymethylcarbonyl, 3-aminophenoxymethylcarbonyl, 4-trifluoromethoxyphenoxymethylcarbonyl, 2-methylthiophenoxymethylcarbonyl, 3-trifluoromethylthiophenoxymethylcarbonyl, 4-cyanophenoxymethylcarbonyl, 2-nitrophenoxymethylcarbonyl, and 4-trifluoromethylphenoxymethylcarbonyl.

[0135] Phenoxyhaloalkylcarbonyl and Z２ Examples of the phenoxyhaloalkylcarbonyl substituted by one or more substituents selected from the above include phenoxydifluoromethylcarbonyl, 2-phenoxy-2,2-difluoroethylcarbonyl, 2-fluorophenoxydichloromethylcarbonyl, 2-chlorophenoxychloromethylcarbonyl, 4-bromophenoxybromomethylcarbonyl, and 4-trifluoromethylphenoxydifluoromethylcarbonyl.

[0136] Examples of the trialkylsilyloxyalkylcarbonyl include trimethylsilyloxymethylcarbonyl, 2-(trimethylsilyloxy)ethylcarbonyl, 1-(trimethylsilyloxy)ethylcarbonyl, 2-(trimethylsilyloxy)ethylcarbonyl, and 2-(t-butyldimethylsilyloxy)ethylcarbonyl, and the like, each of which is selected from the range of carbon numbers specified for that group.

[0137] Examples of the alkoxyalkoxyalkylcarbonyl include methoxymethoxymethylcarbonyl, ethoxymethoxymethylcarbonyl, propyloxymethoxymethylcarbonyl, i-propyloxymethoxymethylcarbonyl, butyloxymethoxymethylcarbonyl, 1-(methoxymethoxy)ethylcarbonyl, 2-(methoxymethoxy)ethylcarbonyl, 2-(ethoxymethoxy)ethylcarbonyl, 2-(ethoxy)ethoxymethylcarbonyl, and the like, each selected from the specified range of carbon numbers.

[0138] Examples of the alkylcarbonylalkylcarbonyl include methylcarbonylmethylcarbonyl, ethylcarbonylmethylcarbonyl, propylcarbonylmethylcarbonyl, i-propylcarbonylmethylcarbonyl, butylcarbonylmethylcarbonyl, i-butylcarbonylmethylcarbonyl, s-butylcarbonylmethylcarbonyl, t-butylcarbonylmethylcarbonyl, pentylcarbonylmethylcarbonyl, 1-(methylcarbonyl)ethylcarbonyl, 2-(methylcarbonyl)ethylcarbonyl, 2-(ethylcarbonyl)ethylcarbonyl, 3-(methylcarbonyl)propylcarbonyl, and the like, and each is selected from the range of carbon numbers specified.

[0139] Examples of the alkylcarbonyloxyalkylcarbonyl include acetoxymethylcarbonyl, propionyloxymethylcarbonyl, butyryloxymethylcarbonyl, i-butyryloxymethylcarbonyl, valeroyloxymethylcarbonyl, i-valeroyloxymethylcarbonyl, 2-methylbutyryloxymethylcarbonyl, pivaloyloxymethylcarbonyl, heptanoyloxymethylcarbonyl, 1-(acetoxy)ethylcarbonyl, 2-(acetoxy)ethylcarbonyl, 2-(propionyloxy)ethylcarbonyl, and 3-(acetoxy)propylcarbonyl, and each is selected from the range of carbon numbers specified for that group.

[0140] Examples of the alkoxycarbonylalkylcarbonyl include methoxycarbonylmethylcarbonyl, ethoxycarbonylmethylcarbonyl, propyloxycarbonylmethylcarbonyl, i-propyloxycarbonylmethylcarbonyl, butyloxycarbonylmethylcarbonyl, 2-(methoxycarbonyl)ethylcarbonyl, 2-(ethoxycarbonyl)ethylcarbonyl, 3-(methoxycarbonyl)propylcarbonyl, and the like, and each is selected from the range of carbon numbers specified.

[0141] Examples of the alkylthioalkylcarbonyl include methylthiomethylcarbonyl, ethylthiomethylcarbonyl, propylthiomethylcarbonyl, i-propylthiomethylcarbonyl, butylthiomethylcarbonyl, i-butylthiomethylcarbonyl, s-butylthiomethylcarbonyl, t-butylthiomethylcarbonyl, pentylthiomethylcarbonyl, 1-(methylthio)ethylcarbonyl, 2-(methylthio)ethylcarbonyl, 2-(ethylthio)ethylcarbonyl, 3-(methylthio)propylcarbonyl, and the like, and each is selected from the range of carbon numbers specified.

[0142] Examples of haloalkylthioalkylcarbonyl include fluoromethylthiomethylcarbonyl, chloromethylthiomethylcarbonyl, bromomethylthiomethylcarbonyl, 2,2,2-trifluoroethylthiomethylcarbonyl, 2-(chloromethylthio)ethylcarbonyl, and the like, each selected from the range of the specified number of carbon atoms.

[0143] Examples of alkylsulfinyl include methylsulfinyl, ethylsulfinyl, propylsulfinyl, i-propylsulfinyl, butylsulfinyl, i-butylsulfinyl, s-butylsulfinyl, t-butylsulfinyl, and the like, each selected from the range of carbon numbers specified for that group.

[0144] Examples of the alkoxycarbonyl include methoxycarbonyl, ethoxycarbonyl, propyloxycarbonyl, i-propyloxycarbonyl, butyloxycarbonyl, s-butyloxycarbonyl, i-butyloxycarbonyl, t-butyloxycarbonyl, pentyloxycarbonyl, (2,2-dimethyl-1-propyl)oxycarbonyl, hexyloxycarbonyl, and heptyloxycarbonyl, and each is selected from the range of carbon numbers specified for that group.

[0145] Examples of the haloalkoxycarbonyl include fluoromethoxycarbonyl, difluoromethoxycarbonyl, trifluoromethoxycarbonyl, 1-fluoroethoxycarbonyl, 2-fluoroethoxycarbonyl, 2-chloroethoxycarbonyl, 2-bromoethoxycarbonyl, 2,2-difluoroethoxycarbonyl, 2,2,2-trifluoroethoxycarbonyl, 1-fluoropropyloxycarbonyl, 2-fluoropropyloxycarbonyl, 3-fluoropropyloxycarbonyl, 3-chloropropyloxycarbonyl, 3-bromopropyloxycarbonyl, (1,3-difluoropropan-2-yl)oxycarbonyl, (2,2-difluoro-1-methyl-ethyl)oxycarbonyl, (2,2,2-trifluoro-1-methyl-ethyl)oxycarbonyl, 4-fluorobutyloxycarbonyl, and 4-chlorobutyloxycarbonyl, and the like, each of which is selected from the range of the specified number of carbon atoms.

[0146] Examples of the cycloalkyloxycarbonyl include cyclopropyloxycarbonyl, cyclobutyloxycarbonyl, cyclopentyloxycarbonyl, cyclohexyloxycarbonyl, and the like, each selected from the range of carbon numbers specified for that group.

[0147] Examples of alkenyloxycarbonyl include ethenyloxycarbonyl, 1-propenyloxycarbonyl, 2-propenyloxycarbonyl, 1-butenyloxycarbonyl, 1-methyl-2-propenyloxycarbonyl, 2-methyl-2-propenyloxycarbonyl, and 1-hexenyloxycarbonyl, and each is selected from the range of carbon numbers specified.

[0148] Examples of haloalkenyloxycarbonyl include 1-chloroethenyloxycarbonyl, 2-chloroethenyloxycarbonyl, 2-fluoroethenyloxycarbonyl, 2,2-dichloroethenyloxycarbonyl, 3-chloro-2-propenyloxycarbonyl, 3-fluoro-2-propenyloxycarbonyl, 2-chloro-2-propenyloxycarbonyl, and 4-chloro-3-butenyloxycarbonyl, and each is selected from the range of carbon numbers specified.

[0149] Examples of the alkynyloxycarbonyl include ethynyloxycarbonyl, 1-propynyloxycarbonyl, 2-propynyloxycarbonyl, 1-butynyloxycarbonyl, 1-methyl-2-propynyloxycarbonyl, 2-methyl-2-propynyloxycarbonyl, and 1-hexynyloxycarbonyl, and the like, each selected from the range of carbon numbers specified for that group.

[0150] Z ２Examples of the phenoxycarbonyl substituted by one or more substituents selected from the above include 2-fluorophenoxycarbonyl, 2-chlorophenoxycarbonyl, 4-bromophenoxycarbonyl, 4-methylphenoxycarbonyl, 2-methoxyphenoxycarbonyl, 3-aminophenoxycarbonyl, 4-trifluoromethoxyphenoxycarbonyl, 2-methylthiophenoxycarbonyl, 3-trifluoromethylthiophenoxycarbonyl, 4-cyanophenoxycarbonyl, 2-nitrophenoxycarbonyl, 4-nitrophenoxycarbonyl, and 4-trifluoromethylphenoxycarbonyl.

[0151] Heterocyclyloxycarbonyl and Z ２ Examples of the heterocyclyloxycarbonyl substituted by one or more substituents selected from the group consisting of (oxiran-2-yl)oxycarbonyl, (2-methyloxiran-2-yl)oxycarbonyl, (3,3-dimethyloxiran-2-yl)oxycarbonyl, (oxetan-2-yl)oxycarbonyl, (oxetan-3-yl)oxycarbonyl, (tetrahydrofuran-2-yl)oxycarbonyl, (tetrahydrofuran-3-yl)oxycarbonyl, (tetrahydrofuran-4-yl)oxycarbonyl, (tetrahydrothiophen-2-yl)oxycarbonyl, tetrahydrothiophen-3-yl)oxycarbonyl, (1,1-dioxytetrahydrothiophen-3-yl)oxycarbonyl, (2,5- (dioxopyrrolidin-1-yl)oxycarbonyl, (tetrahydropyran-3-yl)oxycarbonyl, (tetrahydropyran-4-yl)oxycarbonyl, (tetrahydrothiopyran-4-yl)oxycarbonyl, (1,1-dioxidetetrahydro-2H-thiopyran-4-yl)oxycarbonyl, (1,3-dioxan-5-yl)oxycarbonyl, (2,2-dimethyl-1,3-dioxan-5-yl)oxycarbonyl, (thiophen-2-yl)oxycarbonyl, (thiophen-3-yl)oxycarbonyl, (pyridin-2-yl)oxycarbonyl, (pyridin-3-yl)oxycarbonyl, (pyridin-4-yl)oxycarbonyl and the like, and each may be selected from the range of the number of carbon atoms specified for each.

[0152] Examples of the cycloalkylalkoxycarbonyl include cyclopropylmethoxycarbonyl, 2-cyclopropylethoxyoxycarbonyl, cyclopentylmethoxycarbonyl, and cyclohexylmethoxycarbonyl, each of which is selected from the range of carbon numbers specified.

[0153] Phenylalkoxycarbonyl and Z ２ Examples of the phenylalkoxycarbonyl substituted by one or more substituents selected from the above include benzyloxycarbonyl, 2-fluorobenzyloxycarbonyl, 2-chlorobenzyloxycarbonyl, 3-bromobenzyloxycarbonyl, 4-iodobenzyloxycarbonyl, 4-methylbenzyloxycarbonyl, 2-methoxybenzyloxycarbonyl, 4-aminobenzyloxycarbonyl, 4-trifluoromethoxybenzyloxycarbonyl, 2-methylthiobenzyloxycarbonyl, 3-trifluoromethylthiobenzyloxycarbonyl, 2-cyanobenzyloxycarbonyl, 4-nitrobenzyloxycarbonyl, 2-trifluoromethylbenzyloxycarbonyl, and 2-phenethyloxycarbonyl.

[0154] Heterocyclylalkoxycarbonyl and Z ２Examples of the heterocyclylalkoxycarbonyl substituted by one or more substituents selected from the group consisting of (oxiran-2-yl)methoxycarbonyl, (2-methyloxiran-2-yl)methoxycarbonyl, (3,3-dimethyloxiran-2-yl)methoxycarbonyl, 1-(oxiran-2-yl)ethoxycarbonyl, (oxetan-2-yl)methoxycarbonyl, (oxetan-3-yl)methoxycarbonyl, (tetrahydrofuran-2-yl)methoxycarbonyl, (tetrahydrofuran-3-yl)methoxycarbonyl, (tetrahydrofuran-4-yl)methoxycarbonyl, (tetrahydrothiophen-2-yl)methoxycarbonyl, (1,1-dioxytetrahydro) (thiophen-2-yl)methoxycarbonyl, [(2-oxo-1,3-dioxolan-4-yl)methyl]oxycarbonyl, (tetrahydropyran-2-yl)methoxycarbonyl, (tetrahydropyran-4-yl)methoxycarbonyl, (1,3-dioxan-2-yl)methoxycarbonyl, (thiophen-2-yl)methoxycarbonyl, (thiophen-3-yl)methoxycarbonyl, [(5-methyl-2-oxo-1,3-dioxol-4-yl)methyl]oxycarbonyl, (pyridin-2-yl)methoxycarbonyl, (pyridin-3-yl)methoxycarbonyl, (pyridin-4-yl)methoxycarbonyl and the like, and each may be selected from the range of the number of carbon atoms specified.

[0155] Examples of the cyanoalkoxycarbonyl include cyanomethoxycarbonyl, 1-cyanoethoxycarbonyl, 2-cyanoethoxycarbonyl, and the like, each selected from the range of carbon numbers specified for that group.

[0156] Examples of the hydroxyalkoxycarbonyl include 2-hydroxyethoxycarbonyl, 3-hydroxypropyloxycarbonyl, 3-hydroxybutoxycarbonyl, 2-hydroxy-i-butoxycarbonyl, and 4-hydroxy-2-methylbutoxycarbonyl, each of which is selected from the range of carbon numbers specified.

[0157] Examples of the alkoxyalkoxycarbonyl include methoxymethoxycarbonyl, ethoxymethoxycarbonyl, propyloxymethoxycarbonyl, i-propyloxymethoxycarbonyl, butyloxymethoxycarbonyl, 1-methoxyethoxycarbonyl, 2-methoxyethoxycarbonyl, (1,3-dimethoxypropan-2-yl)oxycarbonyl, (1,3-diethoxypropan-2-yl)oxycarbonyl, (1-methoxy-3-ethoxypropan-2-yl)oxycarbonyl, and the like, and each is selected from the range of carbon numbers specified.

[0158] Examples of haloalkoxyalkoxycarbonyl include fluoromethoxymethoxycarbonyl, chloromethoxymethoxycarbonyl, bromomethoxymethoxycarbonyl, 2,2,2-trifluoroethoxymethoxycarbonyl, and the like, each selected from the range of the specified number of carbon atoms.

[0159] Examples of the trialkylsilyloxyalkoxycarbonyl include trimethylsilyloxymethoxycarbonyl, 2-(trimethylsilyloxy)ethoxycarbonyl, 1-(trimethylsilyloxy)ethoxycarbonyl, and 2-(trimethylsilyloxy)ethoxycarbonyl, and each is selected from the range of carbon numbers specified.

[0160] Examples of the alkyldiphenylsilyloxyalkoxycarbonyl include methyldiphenylsilyloxymethoxycarbonyl, ethyldiphenylsilyloxymethoxycarbonyl, and t-butyldiphenylsilyloxymethoxycarbonyl, each selected from the range of carbon numbers specified.

[0161] Examples of the alkoxyalkoxyalkoxycarbonyl include methoxymethoxymethoxycarbonyl, ethoxymethoxymethoxycarbonyl, propyloxymethoxymethoxycarbonyl, i-propyloxymethoxymethoxycarbonyl, 1-(methoxymethoxy)ethoxycarbonyl, 2-(methoxymethoxy)ethoxycarbonyl, and the like, each selected from the range of carbon numbers specified.

[0162] Examples of the alkylcarbonyloxyalkoxycarbonyl include acetoxymethoxycarbonyl, propionyloxymethoxycarbonyl, butyryloxymethoxycarbonyl, i-butyryloxymethoxycarbonyl, valeroyloxymethoxycarbonyl, i-valeroyloxymethoxycarbonyl, 2-methylbutyryloxymethoxycarbonyl, pivaloyloxymethoxycarbonyl, heptanoyloxymethoxycarbonyl, 1-(acetoxy)ethoxycarbonyl, 2-(acetoxy)ethoxycarbonyl, 2-(propionyloxy)ethoxycarbonyl, and 3-(acetoxy)propyloxycarbonyl, and each is selected from the range of carbon numbers specified for that group.

[0163] Examples of alkylsulfonyloxyalkoxycarbonyl include methylsulfonyloxymethoxycarbonyl, ethylsulfonyloxymethoxycarbonyl, propylsulfonyloxymethoxycarbonyl, i-propylsulfonyloxymethoxycarbonyl, butylsulfonyloxymethoxycarbonyl, i-butylsulfonyloxymethoxycarbonyl, s-butylsulfonyloxymethoxycarbonyl, t-butylsulfonyloxymethoxycarbonyl, 1-(methylsulfonyloxy)ethoxycarbonyl, 2-(methylsulfonyloxy)ethoxycarbonyl, and the like, and each is selected from the range of carbon numbers specified.

[0164] Examples of the alkylcarbonylalkoxycarbonyl include methylcarbonylmethoxycarbonyl, propylcarbonylmethoxycarbonyl, i-propylcarbonylmethoxycarbonyl, 1-(methylcarbonyl)ethoxycarbonyl, 2-(methylcarbonyl)ethoxycarbonyl, and the like, each selected from the range of carbon numbers specified.

[0165] Examples of the alkoxycarbonylalkoxycarbonyl include methoxycarbonylmethoxycarbonyl, ethoxycarbonylmethoxycarbonyl, propyloxycarbonylmethoxycarbonyl, i-propyloxycarbonylmethoxycarbonyl, butyloxycarbonylmethoxycarbonyl, 2-(methoxycarbonyl)ethoxycarbonyl, 2-(ethoxycarbonyl)ethoxycarbonyl, 3-(methoxycarbonyl)propyloxycarbonyl, and the like, and each is selected from the range of carbon numbers specified.

[0166] Examples of the alkylthioalkoxycarbonyl include methylthiomethoxycarbonyl, ethylthiomethoxycarbonyl, propylthiomethoxycarbonyl, i-propylthiomethoxycarbonyl, butylthiomethoxycarbonyl, 2-methylthioethoxycarbonyl, and 1-methylthioethoxycarbonyl, and each is selected from the range of carbon numbers specified.

[0167] Examples of haloalkylthioalkoxycarbonyl include fluoromethylthiomethoxycarbonyl, chloromethylthiomethoxycarbonyl, bromomethylthiomethoxycarbonyl, 2,2,2-trifluoroethylthiomethoxycarbonyl, 2-(chloromethylthio)ethoxycarbonyl, and the like, each selected from the range of the specified number of carbon atoms.

[0168] Examples of alkylsulfinylalkoxycarbonyl include methylsulfinylmethoxycarbonyl, ethylsulfinylmethoxycarbonyl, propylsulfinylmethoxycarbonyl, i-propylsulfinylmethoxycarbonyl, butylsulfinylmethoxycarbonyl, 2-methylsulfinylethoxycarbonyl, 1-methylsulfinylethoxycarbonyl, and the like, each selected from the range of carbon numbers specified for that group.

[0169] Examples of alkylsulfonylalkoxycarbonyl include methylsulfonylmethoxycarbonyl, ethylsulfonylmethoxycarbonyl, propylsulfonylmethoxycarbonyl, i-propylsulfonylmethoxycarbonyl, butylsulfonylmethoxycarbonyl, 2-methylsulfonylethoxycarbonyl, 1-methylsulfonylethoxycarbonyl, and the like, and each is selected from the range of carbon numbers specified.

[0170] Examples of alkylthiocarbonyl include methylthiocarbonyl, ethylthiocarbonyl, propylthiocarbonyl, i-propylthiocarbonyl, butylthiocarbonyl, i-butylthiocarbonyl, s-butylthiocarbonyl, and t-butylthiocarbonyl, each of which is selected from the range of carbon numbers specified.

[0171] Examples of haloalkylthiocarbonyl include fluoromethylthiocarbonyl, chlorodifluoromethylthiocarbonyl, bromodifluoromethylthiocarbonyl, trifluoromethylthiocarbonyl, trichloromethylthiocarbonyl, 2,2,2-trifluoroethylthiocarbonyl, 1,1,2,2-tetrafluoroethylthiocarbonyl, 2-fluoroethylthiocarbonyl, and pentafluoroethylthiocarbonyl, and each is selected from the range of carbon numbers specified.

[0172] Examples of monoalkylaminocarbonyl include methylaminocarbonyl, ethylaminocarbonyl, propylaminocarbonyl, i-propylaminocarbonyl, butylaminocarbonyl, s-butylaminocarbonyl, i-butylaminocarbonyl, t-butylaminocarbonyl, pentylaminocarbonyl, and hexylaminocarbonyl, and each is selected from the range of carbon numbers specified.

[0173] Examples of monohaloalkylaminocarbonyl include fluoromethylaminocarbonyl, difluoromethylaminocarbonyl, trifluoromethylaminocarbonyl, chloromethylaminocarbonyl, bromomethylaminocarbonyl, iodomethylaminocarbonyl, 2-fluoroethylaminocarbonyl, 2-chloroethylaminocarbonyl, 3-fluoropropylaminocarbonyl, 2-fluoropropylaminocarbonyl, and 1-fluoropropylaminocarbonyl, and each is selected from the range of carbon numbers specified.

[0174] Examples of dialkylaminocarbonyl include dimethylaminocarbonyl, diethylaminocarbonyl, dipropylaminocarbonyl, di(i-propyl)aminocarbonyl, dibutylaminocarbonyl, di(s-butyl)aminocarbonyl, di(i-butyl)aminocarbonyl, di(t-butyl)aminocarbonyl, dipentylaminocarbonyl, dihexylaminocarbonyl, ethyl(methyl)aminocarbonyl, and methyl(propyl)aminocarbonyl, and each is selected from the range of carbon numbers specified for that group.

[0175] Examples of di(haloalkyl)aminocarbonyl include di(fluoromethyl)aminocarbonyl, di(chloromethyl)aminocarbonyl, di(bromomethyl)aminocarbonyl, fluoromethyl(methyl)aminocarbonyl, chloromethyl(methyl)aminocarbonyl, chloromethyl(ethyl)aminocarbonyl, di(2-fluoroethyl)aminocarbonyl, and (2-fluoroethyl)methylaminocarbonyl, and each is selected from the range of carbon numbers specified.

[0176] Examples of the alkoxyoxalyl include methoxycarbonylcarbonyl, ethoxycarbonylcarbonyl, i-propyloxycarbonylcarbonyl, t-butoxycarbonylcarbonyl, and the like, each selected from the range of carbon numbers specified.

[0177] Examples of alkylsulfonyl include methylsulfonyl, ethylsulfonyl, propylsulfonyl, i-propylsulfonyl, butylsulfonyl, i-butylsulfonyl, s-butylsulfonyl, and t-butylsulfonyl, each selected from the range of carbon numbers specified.

[0178] Examples of haloalkylsulfonyl include fluoromethylsulfonyl, chloromethylsulfonyl, chlorodifluoromethylsulfonyl, bromodifluoromethylsulfonyl, trifluoromethylsulfonyl, trichloromethylsulfonyl, 2,2,2-trifluoroethylsulfonyl, 1,1,2,2-tetrafluoroethylsulfonyl, 2-fluoroethylsulfonyl, pentafluoroethylsulfonyl, and the like, and each is selected from the range of carbon numbers specified.

[0179] Examples of cycloalkylsulfonyl include cyclopropanesulfonyl, cyclobutanesulfonyl, cyclopentanesulfonyl, cyclohexanesulfonyl, and the like, each selected from the range of carbon numbers specified for that group.

[0180] Examples of alkenylsulfonyl include ethenylsulfonyl, 1-propenylsulfonyl, 2-propenylsulfonyl, 1-butenylsulfonyl, 1-methyl-2-propenylsulfonyl, 2-methyl-2-propenylsulfonyl, and 1-hexenylsulfonyl, and each is selected from the range of carbon numbers specified.

[0181] Examples of haloalkenylsulfonyl include 1-chloroethenylsulfonyl, 2-chloroethenylsulfonyl, 2-fluoroethenylsulfonyl, 2,2-dichloroethenylsulfonyl, 3-chloro-2-propenylsulfonyl, 3-fluoro-2-propenylsulfonyl, 2-chloro-2-propenylsulfonyl, 4-chloro-3-butenylsulfonyl, and the like, and each is selected from the range of carbon numbers specified.

[0182] Z ２Examples of the phenylsulfonyl substituted by one or more substituents selected from the above include 2-fluorophenylsulfonyl, 2-chlorophenylsulfonyl, 4-bromophenylsulfonyl, 4-methylphenylsulfonyl, 2-methoxyphenylsulfonyl, 3-aminophenylsulfonyl, 4-trifluoromethoxyphenylsulfonyl, 2-methylthiophenylsulfonyl, 3-trifluoromethylthiophenylsulfonyl, 4-cyanophenylsulfonyl, 2-nitrophenylsulfonyl, and 4-trifluoromethylphenylsulfonyl.

[0183] Heterocyclylsulfonyl and Z ２ Examples of the heterocyclylsulfonyl substituted by one or more substituents selected from include (furan-2-yl)sulfonyl, (3-methylfuran-2-yl)sulfonyl, (furan-3-yl)sulfonyl, (thiophen-2-yl)sulfonyl, (thiophen-3-yl)sulfonyl, (pyridin-2-yl)sulfonyl, (pyridin-3-yl)sulfonyl, (pyridin-4-yl)sulfonyl, and the like, each selected from the range of carbon numbers specified for each.

[0184] Examples of the cycloalkylalkylsulfonyl include cyclopropylmethylsulfonyl, 2-cyclopropylethylsulfonyl, cyclopentylmethylsulfonyl, cyclohexylmethylsulfonyl, and the like, each selected from the range of carbon numbers specified.

[0185] Phenylalkylsulfonyl and Z ２Examples of the phenylalkylsulfonyl substituted by one or more substituents selected from the above include benzylsulfonyl, 2-fluorobenzylsulfonyl, 3-fluorobenzylsulfonyl, 4-fluorobenzylsulfonyl, 2-chlorobenzylsulfonyl, 3-bromobenzylsulfonyl, 4-iodobenzylsulfonyl, 2,4-difluorobenzylsulfonyl, 2-methylbenzylsulfonyl, 3-methylbenzylsulfonyl, 4-methylbenzylsulfonyl, 2-methoxybenzylsulfonyl, 4-aminobenzylsulfonyl, 4-trifluoromethoxybenzylsulfonyl, 2-methylthiobenzylsulfonyl, 3-trifluoromethylthiobenzylsulfonyl, 2-cyanobenzylsulfonyl, 4-nitrobenzylsulfonyl, 2-trifluoromethylbenzylsulfonyl, 2-phenethylsulfonyl, and the like, and each is selected from the range of carbon numbers specified for each.

[0186] Examples of the alkoxyalkylsulfonyl include methoxymethylsulfonyl, ethoxymethylsulfonyl, i-propyloxymethylsulfonyl, 3-(methoxy)butylsulfonyl, 2-(methoxy)-i-butylsulfonyl, and the like, each selected from the range of carbon numbers specified.

[0187] Examples of the monoalkylaminosulfonyl include methylaminosulfonyl, ethylaminosulfonyl, propylaminosulfonyl, i-propylaminosulfonyl, butylaminosulfonyl, s-butylaminosulfonyl, i-butylaminosulfonyl, t-butylaminosulfonyl, pentylaminosulfonyl, and hexylaminosulfonyl, and each of these is selected from the range of carbon atoms specified for that group.

[0188] Examples of dialkylaminosulfonyl include dimethylaminosulfonyl, diethylaminosulfonyl, dipropylaminosulfonyl, di(i-propyl)aminosulfonyl, dibutylaminosulfonyl, di(s-butyl)aminosulfonyl, di(i-butyl)aminosulfonyl, di(t-butyl)aminosulfonyl, dipentylaminosulfonyl, dihexylaminosulfonyl, ethyl(methyl)aminosulfonyl, methyl(propyl)aminosulfonyl, and the like, and each is selected from the range of carbon numbers specified for each.

[0189] Examples of alkylthio include methylthio, ethylthio, propylthio, i-propylthio, butylthio, i-butylthio, s-butylthio, and t-butylthio, each of which is selected from the range of carbon numbers specified.

[0190] Examples of haloalkylthio include fluoromethylthio, chloromethylthio, chlorodifluoromethylthio, bromodifluoromethylthio, trifluoromethylthio, trichloromethylthio, 2,2,2-trifluoroethylthio, 1,1,2,2-tetrafluoroethylthio, 2-fluoroethylthio, pentafluoroethylthio, and the like, each of which is selected from the range of carbon atoms specified for that group.

[0191] Examples of the alkoxy include methoxy, ethoxy, propyloxy, i-propyloxy, butyloxy, i-butyloxy, s-butyloxy, t-butyloxy, pentyloxy, 1-methylbutyloxy, 2-methylbutyloxy, 3-methylbutyloxy, 1,1-dimethylpropyloxy, 1,2-dimethylpropyloxy, 2,2-dimethylpropyloxy, 1-ethylpropyloxy, hexyloxy, 1-methylpentyloxy, 2-methylpentyloxy, 3-methylpentyloxy, 4-methylpentyloxy, 1,1-dimethylbutyloxy, 1,2-dimethylbutyloxy, 1,3-dimethylbutyloxy, 2,2-dimethylbutyloxy, 2,3-dimethylbutyloxy, 3,3-dimethylbutyloxy, 1-ethylbutyloxy, 2-ethylbutyloxy, 1,1,2-trimethylpropyloxy, 1,2,2-trimethylpropyloxy, 1-ethyl-1-methylpropyloxy, 1-ethyl-2-methylpropyloxy, and the like, each of which is selected from the range of the number of carbon atoms specified.

[0192] Examples of haloalkoxy include fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, bromodifluoromethoxy, dichlorofluoromethoxy, chloromethoxy, dichloromethoxy, trichloromethoxy, bromomethoxy, 1-fluoroethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 1,1,2,2-tetrafluoroethoxy, pentafluoroethoxy, 2,2,2-trichloroethoxy, 2,2,2-trifluoroethoxy, 1-fluoropropyloxy, 2-fluoropropyloxy, 3-fluoropropyloxy, 3-chloropropyloxy, 3-bromopropyloxy, 1-fluorobutyloxy, 2-fluorobutyloxy, 3-fluorobutyloxy, 4-fluorobutyloxy, 4-chlorobutyloxy, and the like, and each is selected from the range of the specified number of carbon atoms.

[0193] "R ３ and R ４ can be bonded to each other to form a 3- to 7-membered ring” means, for example, that ３ and R４ is capable of forming cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, epoxy, tetrahydrofuran, tetrahydropyran, tetrahydrothiophene, tetrahydrothiopyran, pyrrolidine, piperidine, etc., which contains a carbon to which is bonded.

[0194] Examples of hydroxyalkyl include hydroxymethyl, 1-hydroxyethyl, 2-hydroxyethyl, 1-hydroxypropyl, 2-hydroxypropyl, 3-hydroxypropyl, 1-hydroxy-1-methylethyl, 2-hydroxy-1-methylethyl, and 2-hydroxy-1,1-dimethylethyl, each of which is selected from the range of carbon numbers specified.

[0195] Examples of monoalkylaminoalkyl include methylaminomethyl, ethylaminomethyl, propylaminomethyl, i-propylaminomethyl, butylaminomethyl, 2-(methylamino)ethyl, 2-(ethylamino)ethyl, and 3-(methylamino)propyl, each of which is selected from the range of carbon atoms specified for that group.

[0196] Examples of dialkylaminoalkyl include dimethylaminomethyl, diethylaminomethyl, ethyl(methyl)aminomethyl, methyl(propyl)aminomethyl, butyl(methyl)aminomethyl, 2-(diethylamino)ethyl, 2-{ethyl(methyl)amino}propyl, and the like, each selected from the range of carbon numbers specified for that group.

[0197] Z ２Examples of the phenyl which may be substituted by one or more substituents selected from the group consisting of phenyl, 2-fluorophenyl, 3-fluorophenyl, 4-fluorophenyl, 2-chlorophenyl, 3-bromophenyl, 4-iodophenyl, 2,3-difluorophenyl, 2,4-difluorophenyl, 2,6-difluorophenyl, 3,4-difluorophenyl, 3,5-difluorophenyl, 2,4-dichlorophenyl, 2-fluoro-4-chlorophenyl, 2,3,4,5,6-pentafluorophenyl, 2-methylphenyl, 2,5-dimethylphenyl, 4-ethenylphenyl, 2-ethynylphenyl, 3-cyclopropylphenyl, 2-cyclopentylphenyl, 4-cyclohexylphenyl, 2-methoxyphenyl, 3,4-dimethoxyphenyl, 3,4,5-trimethoxyphenyl, 4-methoxymethylphenyl, 2-aminophenyl, and 4-dimethylaminophenyl. nyl, 2-aminocarbonylphenyl, 2-dimethylaminocarbonylphenyl, 4-trifluoromethoxyphenyl, 2-difluoromethoxyphenyl, 2-ethenyloxyphenyl, 3-cyclopropyloxyphenyl, 2-biphenyl, 4-acetylphenyl, 3-methoxycarbonylphenyl, 2-methylthiophenyl, 3-trifluoromethylthiophenyl, 4-difluoromethylthiophenyl, 2-methylsulfinylphenyl, 3-trifluoromethylsulfinylphenyl, 4-difluoromethylsulfinylphenyl, 2-methylsulfonylphenyl, 3-trifluoromethylsulfonylphenyl, 4-difluoromethylsulfonylphenyl, 2-cyanophenyl, 3-nitrophenyl, 4-trifluoromethylphenyl, 2-difluoromethylphenyl, 2,3-methylenedioxyphenyl, 3,4-methylenedioxyphenyl and the like.

[0198] Examples of heterocyclyl are shown below: thienyl is thiophen-2-yl or thiophen-3-yl, furyl is furan-2-yl or furan-3-yl, pyrrolyl is pyrrol-1-yl, pyrrol-2-yl or pyrrol-3-yl, oxazolyl is oxazol-2-yl, oxazol-4-yl or oxazol-5-yl, isoxazolyl is isoxazol-3-yl, isoxazol-4-yl or isoxazol-5-yl, isoxazolinyl is isoxazolin-3-yl, isoxazolin-4-yl or isooxazol-5-yl. thiazolyl is thiazol-2-yl, thiazol-4-yl or thiazol-5-yl; isothiazolyl is isothiazol-3-yl, isothiazol-4-yl or isothiazol-5-yl; pyrazolyl is pyrazol-1-yl, pyrazol-3-yl, pyrazol-4-yl or pyrazol-5-yl; imidazolyl is imidazol-1-yl, imidazol-2-yl or imidazol-4-yl; 1,3,4-oxadiazolyl is 1,3,4-oxadiazol-2-yl. 1,2,4-oxadiazolyl is 1,2,4-oxadiazol-3-yl or 1,2,4-oxadiazol-5-yl; 1,3,4-thiadiazolyl is 1,3,4-thiadiazol-2-yl; 1,2,4-thiadiazolyl is 1,2,4-thiadiazol-3-yl or 1,2,4-thiadiazol-5-yl; 1,2,4-triazolyl is 1,2,4-triazol-1-yl, 1,2,4-triazol-3-yl or 1,2,4-triazol-5-yl; and 1,2,3-thiadiazolyl is 1,2,3 -thiadiazol-4-yl or 1,2,3-thiadiazol-5-yl, 1,2,3-triazolyl is 1,2,3-triazol-1-yl, 1,2,3-triazol-2-yl or 1,2,3-triazol-4-yl, 1,2,3,4-tetrazolyl is 1,2,3,4-tetrazol-1-yl, 1,2,3,4-tetrazol-2-yl or 1,2,3,4-tetrazol-5-yl, pyridyl is pyridin-2-yl, pyridin-3-yl or pyridin-4-yl, pyrimidinyl is pyrimidin-2-yl,pyrimidin-4-yl or pyrimidin-5-yl, pyrazinyl is pyrazin-2-yl, pyridazinyl is pyridazin-3-yl or pyridazin-4-yl, 1,3,5-triazinyl is 1,3,5-triazin-2-yl, 1,2,4-triazinyl is 1,2,4-triazin-3-yl, 1,2,4-triazin-5-yl or 1,2,4-triazin-6-yl, benzothienyl is benzothiophen-2-yl, benzothiophen-3-yl, benzothiophen-4-yl, benzothiophen-5-yl, benzothiophen-6-yl, benzofuryl is benzofuran-2-yl, benzofuran-3-yl, benzofuran-4-yl, benzofuran-5-yl, benzofuran-6-yl or benzofuran-7-yl; indolyl is indol-1-yl, indol-2-yl, indol-3-yl, indol-4-yl, indol-5-yl, indol-6-yl or indol-7-yl; benzothiazolyl is benzothiazol-2-yl, benzothiazol-4-yl, benzothiazol-5-yl, benzothiazol-6-yl or benzothiazol-7-yl. benzimidazolyl is benzimidazol-1-yl, benzimidazol-2-yl, benzimidazol-4-yl, benzimidazol-5-yl, benzimidazol-6-yl or benzimidazol-7-yl; benzisoxazolyl is benzisoxazol-3-yl, benzisoxazol-4-yl, benzisoxazol-5-yl, benzisoxazol-6-yl or benzisoxazol-7-yl; benzisothiazolyl is benzisothiazolyl. azol-3-yl, benzisothiazol-4-yl, benzisothiazol-5-yl, benzisothiazol-6-yl or benzisothiazol-7-yl; indazolyl is indazol-1-yl, indazol-3-yl, indazol-4-yl, indazol-5-yl, indazol-6-yl or indazol-7-yl; benzoxazolyl is benzoxazol-2-yl, benzoxazol-4-yl, benzoxazol-5-yl, benzoxazol-6-yl or benzoxazol-7-yl;Quinolyl is quinolin-2-yl, quinolin-3-yl, quinolin-4-yl, quinolin-5-yl, quinolin-6-yl, quinolin-7-yl or quinolin-8-yl; isoquinolyl is isoquinolin-1-yl, isoquinolin-3-yl, isoquinolin-4-yl, isoquinolin-5-yl, isoquinolin-6-yl, isoquinolin-7-yl or isoquinolin-8-yl; quinoxalinyl is quinoxalin-2-yl, quinoxalin-3-yl, quinoxalin-5-yl, quinoxalin-6-yl, quinoxalin-7-yl or quinoxalin-8-yl. phthalazinyl is phthalazin-1-yl, phthalazin-4-yl, phthalazin-5-yl, phthalazin-6-yl, phthalazin-7-yl or phthalazin-8-yl; cinnolinyl is cinnolin-3-yl, cinnolin-4-yl, cinnolin-5-yl, cinnolin-6-yl, cinnolin-7-yl or cinnolin-8-yl; quinazolinyl is quinazolin-2-yl, quinazolin-4-yl, quinazolin-5-yl, quinazolin-6-yl, quinazolin-7-yl or quinazolin-8-yl; Xylanyl is oxiran-2-yl, oxetanyl is oxetan-2-yl or oxetan-3-yl, tetrahydrofuranyl is tetrahydrofuran-2-yl or tetrahydrofuran-3-yl, tetrahydrothienyl is tetrahydrothiophen-2-yl or tetrahydrothiophen-3-yl, 1,1-dioxytetrahydrothienyl is 1,1-dioxytetrahydrothiophen-2-yl or 1,1-dioxytetrahydrothiophen-3-yl, tetrahydropyranyl is tetrahydropyran-2-yl, tetrahydrothienyl is tetrahydrothien ... tetrahydropyran-3-yl or tetrahydropyran-4-yl, tetrahydrothiopyranyl is tetrahydrothiopyran-2-yl, tetrahydrothiopyran-3-yl or tetrahydrothiopyran-4-yl, 1,3-dioxanyl is 1,3-dioxan-2-yl, 1,3-dioxan-4-yl or 1,3-dioxan-5-yl, 2-oxo-1,3-dioxolanyl is 2-oxo-1,3-dioxolan-4-yl, and 2-oxo-1,3-dioxolyl is 2-oxo-1,3-dioxol-4-yl,2,5-dioxopyrrolidinyl is 2,5-dioxopyrrolidin-1-yl.

[0199] Z ２ Examples of the phenylaminocarbonyl substituted by one or more substituents selected from the above include 2-fluorophenylaminocarbonyl, 2-chlorophenylaminocarbonyl, 4-bromophenylaminocarbonyl, 4-methylphenylaminocarbonyl, 2-methoxyphenylaminocarbonyl, 3-aminophenylaminocarbonyl, 4-trifluoromethoxyphenylaminocarbonyl, 2-methylthiophenylaminocarbonyl, 3-trifluoromethylthiophenylaminocarbonyl, 4-cyanophenylaminocarbonyl, 2-nitrophenylaminocarbonyl, and 4-trifluoromethylphenylaminocarbonyl.

[0200] Phenylalkylaminocarbonyl and Z ２ Examples of the phenylalkylaminocarbonyl substituted by one or more substituents selected from the above include benzylaminocarbonyl, 2-fluorobenzylaminocarbonyl, 2-chlorobenzylaminocarbonyl, 3-bromobenzylaminocarbonyl, 4-iodobenzylaminocarbonyl, 4-methylbenzylaminocarbonyl, 2-methoxybenzylaminocarbonyl, 4-aminobenzylaminocarbonyl, 4-trifluoromethoxybenzylaminocarbonyl, 2-methylthiobenzylaminocarbonyl, 3-trifluoromethylthiobenzylaminocarbonyl, 2-cyanobenzylaminocarbonyl, 4-nitrobenzylaminocarbonyl, 2-trifluoromethylbenzylaminocarbonyl, and 2-phenethylaminocarbonyl.

[0201] Z ２Examples of the phenoxy substituted by one or more substituents selected from the above include 2-fluorophenoxy, 2-chlorophenoxy, 4-bromophenoxy, 4-methylphenoxy, 2-methoxyphenoxy, 3-aminophenoxy, 4-trifluoromethoxyphenoxy, 2-methylthiophenoxy, 3-trifluoromethylthiophenoxy, 4-cyanophenoxy, 2-nitrophenoxy, and 4-trifluoromethylphenoxy.

[0202] Z ２ Examples of the phenylthio substituted by one or more substituents selected from the above include 2-fluorophenylthio, 2-chlorophenylthio, 4-bromophenylthio, 4-methylphenylthio, 2-methoxyphenylthio, 3-aminophenylthio, 4-trifluoromethoxyphenylthio, 2-methylthiophenylthio, 3-trifluoromethylthiophenylthio, 4-cyanophenylthio, 2-nitrophenylthio, and 4-trifluoromethylphenylthio.

[0203] Examples of monoalkylamino include methylamino, ethylamino, propylamino, i-propylamino, butylamino, s-butylamino, i-butylamino, t-butylamino, pentylamino, hexylamino, etc., each of which is selected from the range of carbon atoms specified. Examples of di(alkyl)amino include dimethylamino, diethylamino, dipropylamino, di(i-propyl)amino, dibutylamino, di(s-butyl)amino, di(i-butyl)amino, di(t-butyl)amino, dipentylamino, dihexylamino, ethyl(methyl)amino, methyl(propyl)amino, etc., each of which is selected from the range of carbon atoms specified.

[0204] Examples of alkylcarbonyloxy include acetoxy, propionyloxy, butyryloxy, i-butyryloxy, valeroyloxy, i-valeroyloxy, 2-methylbutyryloxy, pivaloyloxy, and heptanoyloxy, and each is selected from the range of carbon numbers specified.

[0205] "R on the same carbon ５ and R ６are bonded to each other to form an oxygen atom, a sulfur atom, and a nitrogen atom (the nitrogen atom is C １ ~C ６ Alkyl, C ２ ~C ６ Alkenyl, C ２ ~C ６ Alkynyl, or C ３ ~C ６ The phrase "can form an optionally substituted 3- to 7-membered ring or can form an olefin" means, for example, that R on the same carbon is optionally interrupted by one or two heteroatoms selected from the group consisting of R ５ and R ６ is R ５ and R ６ is capable of forming cyclopropyl, dichlorocyclopropyl, dimethylcyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, epoxy, tetrahydrofuran, tetrahydropyran, tetrahydrothiophene, tetrahydrothiopyran, pyrrolidine, piperidine, etc., which contains a carbon to which is bonded.

[0206] Two R on adjacent carbons ５ can be taken together with the carbon atoms to which they are attached to form a 3- to 8-membered carbocyclic or heterocyclic ring, wherein the heterocyclic ring contains one or two heteroatoms selected from oxygen, sulfur, or nitrogen atoms. The nitrogen atom is C １ ~C ６ Alkyl, C ２ ~C ６ Alkenyl, C ２ ~C ６ Alkynyl, or C ３ ~C ６ It may be substituted by cycloalkyl. The 3- to 8-membered carbocyclic or heterocyclic ring may be optionally substituted. Examples of the carbocyclic ring include a benzene ring, a cyclopropane ring, a cyclobutane ring, a cyclopentane ring, a cyclohexane ring, a cycloheptane ring, and a cyclooctane ring. Examples of the heterocyclic ring include furan, tetrahydrofuran, thiophene, tetrahydrothiophene, pyrrole, pyrrolidine, pyridine, piperidine, and pyrimidine.

[0207] "R ５ and R ６ is R on the adjacent carbon ５ or R ６ "can form a bond together with" means, for example, ５ and R ６ The carbon bonded to R ５ and R ６ represents that a double bond can be formed between the carbon atom to which the group is bonded.

[0208] Alkenyloxy includes ethenyloxy, 1-propenyloxy, 2-propenyloxy, 1-butenyloxy, 1-methyl-2-propenyloxy, 2-methyl-2-propenyloxy, 1-hexenyloxy, and the like, each selected from the range of carbon numbers specified.

[0209] Examples of the alkynyloxy include ethynyloxy, 1-propynyloxy, 2-propynyloxy, 1-butynyloxy, 1-methyl-2-propynyloxy, 2-methyl-2-propynyloxy, 1-hexynyloxy, and the like, each selected from the range of carbon numbers specified.

[0210] The cycloalkylalkyloxy includes cyclopropylmethoxy, 2-cyclopropylethoxy, cyclopentylmethoxy, cyclohexylmethoxy, and the like, each selected from the range of carbon numbers specified.

[0211] Examples of phenylalkyloxy include benzyloxy, 2-fluorobenzyloxy, 3-fluorobenzyloxy, 4-fluorobenzyloxy, 2-chlorobenzyloxy, 3-bromobenzyloxy, 4-iodobenzyloxy, 2,4-difluorobenzyloxy, 2-methylbenzyloxy, 3-methylbenzyloxy, 4-methylbenzyloxy, 2-methoxybenzyloxy, 4-aminobenzyloxy, 4-trifluoromethoxybenzyloxy, 2-methylthiobenzyloxy, 3-trifluoromethylthiobenzyloxy, 2-cyanobenzyloxy, 4-nitrobenzyloxy, 2-trifluoromethylbenzyloxy, and 2-phenethyloxy, and each is selected from the range of carbon numbers specified for that group.

[0212] Z ２ Examples of the phenylcarbonyloxy substituted by one or more substituents selected from the above include phenylcarbonyloxy, 2-fluorophenylcarbonyloxy, 2-chlorophenylcarbonyloxy, 3-bromophenylcarbonyloxy, 4-iodophenylcarbonyloxy, 4-methylphenylcarbonyloxy, 2-methoxyphenylcarbonyloxy, 4-aminophenylcarbonyloxy, 4-trifluoromethoxyphenylcarbonyloxy, 2-methylthiophenylcarbonyloxy, 3-trifluoromethylthiophenylcarbonyloxy, 2-cyanophenylcarbonyloxy, 4-nitrophenylcarbonyloxy, 2-trifluoromethylphenylcarbonyloxy, and the like, and each is selected from the range of carbon numbers specified for that group.

[0213] Z ２ Examples of the heterocyclylcarbonyloxy substituted by one or more substituents selected from the above include (tetrahydrofuran-2-yl)carbonyloxy, (tetrahydrofuran-3-yl)carbonyloxy, (tetrahydrothiophen-2-yl)carbonyloxy, (pyrrolidin-1-yl)carbonyloxy, (tetrahydropyran-4-yl)carbonyloxy, (furan-2-yl)carbonyloxy, (3-methylfuran-2-yl)carbonyloxy, (furan-3-yl)carbonyloxy, (thiophen-2-yl)carbonyloxy, (thiophen-3-yl)carbonyloxy, (1H-imidazol-1-yl)carbonyloxy, (pyridin-2-yl)carbonyloxy, (pyridin-3-yl)carbonyloxy, (pyridin-4-yl)carbonyloxy, and the like, and each is selected from the range of the number of carbon atoms specified.

[0214] Examples of the alkoxycarbonyloxy include methoxycarbonyloxy, ethoxycarbonyloxy, propyloxycarbonyloxy, i-propyloxycarbonyloxy, butyloxycarbonyloxy, etc., each of which is selected from the range of carbon numbers specified. Examples of the alkylthiocarbonyloxy include methylthiocarbonyloxy, ethylthiocarbonyloxy, propylthiocarbonyloxy, i-propylthiocarbonyloxy, butylthiocarbonyloxy, i-butylthiocarbonyloxy, s-butylthiocarbonyloxy, t-butylthiocarbonyloxy, etc., each of which is selected from the range of carbon numbers specified.

[0215] Examples of alkylsulfonyloxy include methylsulfonyloxy, ethylsulfonyloxy, propylsulfonyloxy, i-propylsulfonyloxy, butylsulfonyloxy, i-butylsulfonyloxy, s-butylsulfonyloxy, and t-butylsulfonyloxy, and each is selected from the range of carbon numbers specified.

[0216] Examples of haloalkylsulfonyloxy include fluoromethylsulfonyloxy, chloromethylsulfonyloxy, chlorodifluoromethylsulfonyloxy, bromodifluoromethylsulfonyloxy, trifluoromethylsulfonyloxy, trichloromethylsulfonyloxy, 2,2,2-trifluoroethylsulfonyloxy, 1,1,2,2-tetrafluoroethylsulfonyloxy, 2-fluoroethylsulfonyloxy, pentafluoroethylsulfonyloxy, and the like, and each is selected from the range of carbon numbers specified.

[0217] Dialkylphosphoroxy includes dimethylphosphoroxy, dimethylphosphoroxy, dipropylphosphoroxy, etc., each selected from the range of carbon numbers specified.

[0218] Examples of trialkylsilyloxy include trimethylsilyloxy, triethylsilyloxy, and t-butyldimethylsilyloxy, each of which is selected from the range of carbon numbers specified.

[0219] Examples of haloalkylsulfinyl include fluoromethylsulfinyl, chloromethylsulfinyl, chlorodifluoromethylsulfinyl, bromodifluoromethylsulfinyl, trifluoromethylsulfinyl, trichloromethylsulfinyl, 2,2,2-trifluoroethylsulfinyl, 1,1,2,2-tetrafluoroethylsulfinyl, 2-fluoroethylsulfinyl, pentafluoroethylsulfinyl, and the like, and each is selected from the range of carbon numbers specified.

[0220] Z ２ Examples of the phenylsulfinyl substituted by one or more substituents selected from the above include 2-fluorophenylsulfinyl, 2-chlorophenylsulfinyl, 4-bromophenylsulfinyl, 4-methylphenylsulfinyl, 2-methoxyphenylsulfinyl, 3-aminophenylsulfinyl, 4-trifluoromethoxyphenylsulfinyl, 2-methylthiophenylsulfinyl, 3-trifluoromethylthiophenylsulfinyl, 4-cyanophenylsulfinyl, 2-nitrophenylsulfinyl, 4-trifluoromethylphenylsulfinyl, and the like.

[0221] Dialkylamino includes dimethylamino, diethylamino, ethyl(methyl)amino, methyl(propyl)amino, butyl(methyl)amino, etc., each selected from the range of carbon numbers specified.

[0222] Examples of alkylcarbonylamino include acetylamino, propionylamino, butyrylamino, i-butyrylamino, valeroylamino, i-valeroylamino, 2-methylbutyrylamino, pivaloylamino, hexanoylamino, 2-ethylbutyrylamino, 2-methylvaleroylamino, and 4-methylvaleroylamino, and each is selected from the range of carbon atoms specified for that group.

[0223] Examples of bis(alkylcarbonyl)amino include bisacetylamino, N-acetyl-N-propionylamino, and N-acetyl-N-pivaloylamino, each of which is selected from the range of carbon numbers specified.

[0224] Examples of haloalkylsulfonylamino include fluoromethylsulfonylamino, chloromethylsulfonylamino, chlorodifluoromethylsulfonylamino, bromodifluoromethylsulfonylamino, trifluoromethylsulfonylamino, trichloromethylsulfonylamino, 2,2,2-trifluoroethylsulfonylamino, 1,1,2,2-tetrafluoroethylsulfonylamino, 2-fluoroethylsulfonylamino, pentafluoroethylsulfonylamino, and the like, and each is selected from the range of carbon numbers specified.

[0225] "Two Xs connected to adjacent carbon or nitrogen atoms on a benzene ring or heterocycle, together with the ring atoms to which they are attached, form a 4- to 6-membered carbocyclic or heterocyclic ring, the heterocyclic ring containing one or two heteroatoms selected from the group consisting of oxygen, sulfur, and nitrogen atoms, and the nitrogen atom is C １ ~C ６ Alkyl, C ２ ~C ６ Alkenyl, C ２ ~C ６ Alkynyl, or C ３ ~C ６ The phrase "optionally substituted by cycloalkyl" means that, for example, indene, dihydroindene, naphthalene, dihydronaphthalene, tetrahydronaphthalene, benzofuran, dihydrobenzofuran, chromene, chroman, benzothiophene, dihydrobenzothiophene, benzoxazole, benzothiazole, thiochromene, thiochroman, indole, indoline, quinoline, dihydroquinoline, tetrahydroquinoline, cyclopentapyridine, pyrrolopyridine, naphthyridine, pyrazolopyridine, triazolopyrimidine, etc. can be formed, which contains a benzene ring or a heterocycle to which X is bonded.

[0226] "Two Y's may be joined together with adjacent carbon or nitrogen atoms on the benzene ring to form a 5- or 6-membered carbocyclic ring or a 5- or 6-membered heterocyclic ring, wherein the heterocyclic ring is composed of oxygen atoms, sulfur atoms, and nitrogen atoms (the nitrogen atoms are C １ ~C ６ Alkyl, C ２ ~C ６Alkenyl, C ２ ~C ６ Alkynyl, or C ３ ~C ６ and the carbocyclic or heterocyclic ring is optionally substituted with one or more halogen atoms" means that, for example, indene, dihydroindene, naphthalene, dihydronaphthalene, tetrahydronaphthalene, benzofuran, dihydrobenzofuran, chromene, chroman, benzothiophene, dihydrobenzothiophene, benzoxazole, benzothiazole, thiochromene, thiochroman, indole, indoline, quinoline, dihydroquinoline, tetrahydroquinoline, cyclopentapyridine, pyrrolopyridine, naphthyridine, pyrazolopyridine, triazolopyrimidine, etc. can be formed containing a benzene ring or heterocyclic ring to which Y is bonded.

[0227] "Two Zs ２ may be joined together with an adjacent carbon atom or nitrogen atom on the benzene ring or heterocycle to form a 5- or 6-membered carbocyclic ring or a 5- or 6-membered heterocyclic ring, wherein the heterocyclic ring is free from oxygen atoms, sulfur atoms, and nitrogen atoms (the nitrogen atoms are C １ ~C ６ Alkyl, C ２ ~C ６ Alkenyl, C ２ ~C ６ Alkynyl, or C ３ ~C ６ The term "containing one or two heteroatoms selected from the group consisting of carbocyclic or heterocyclic rings, which may be substituted by one or more halogens" refers to, for example, Z ２and the like, which contains a benzene ring or a heterocycle to which is bonded, can form indene, dihydroindene, naphthalene, dihydronaphthalene, tetrahydronaphthalene, benzofuran, dihydrobenzofuran, benzoxazole, benzothiazole, chromene, chroman, benzothiophene, dihydrobenzothiophene, thiochromene, thiochroman, indole, indoline, quinoline, dihydroquinoline, tetrahydroquinoline, cyclopentapyridine, pyrrolopyridine, naphthyridine, pyrazolopyridine, triazolopyrimidine, etc.

[0228] The following symbols in the tables in this specification represent the corresponding groups as described below. For example, Me represents a methyl group, Et represents an ethyl group, n-Pr represents a normal propyl group, i-Pr represents an isopropyl group, c-Pr represents a cyclopropyl group, n-Bu represents a normal butyl group, i-Bu represents an isobutyl group, s-Bu represents a secondary butyl group, c-Bu represents a cyclobutyl group, t-Bu represents a tertiary butyl group, n-Pen represents a normal pentyl group, c-Pen represents a cyclopentyl group, n-Hex represents a normal hexyl group, c-Hex represents a cyclohexyl group, n-Hept represents a normal heptyl group, allyl represents a 2-propen-1-yl group, Ph represents a phenyl group, 2-Py represents a pyridin-2-yl group, Prorargyl represents a 2-propyn-1-yl group, Bn represents a benzenemethyl group, CN represents a cyano group, Ac represents an acetyl group, Bz represents a benzenecarbonyl group, Boc represents a tertiary-butoxycarbonyl group, Ms represents a methanesulfonyl group, Tf represents a trifluoromethanesulfonyl group, TBDMS represents a tertiary-butyldimethylsilyl group, TBDPS represents a tertiary-butyldiphenylsilyl group, MOM represents a methoxymethyl group, OMe represents a methoxy group, and OPh represents a phenoxy group.

[0229] Representative methods for producing the compound represented by formula [1] (Compound A) are exemplified below, but the methods are not limited to these. As a reaction apparatus, a magnetic stirrer, a mechanical stirrer, or a microwave synthesis apparatus can also be used.

[0230] <Production Method 1> The compound represented by formula [1] can be produced by a method consisting of the reaction scheme illustrated below.

[0231]

[0232] (In the formula, R １ , R ２ , R ３ , R ４ , A, E, W, X, Y, m, n, o, and p are as defined in formula [1] of (1) above, and L １ represents a leaving group such as a halogen).

[0233] (Step 1) A compound represented by formula [2] and a compound represented by formula [3] are reacted in a solvent in the presence of a base to produce a compound represented by formula [4]. The amount of the compound of formula [3] used in this step may be appropriately selected from the range of 0.5 to 10 moles per mole of the compound of formula [2], and is preferably 1.0 to 1.2 moles. Examples of bases that can be used in this step include organic amines such as triethylamine, pyridine, 4-dimethylaminopyridine, N,N-dimethylaniline, and 1,8-diazabicyclo[5.4.0]-7-undecene; metal carbonates such as sodium carbonate, potassium carbonate, magnesium carbonate, and calcium carbonate; metal bicarbonates such as sodium bicarbonate and potassium bicarbonate; metal carboxylates typified by metal acetates such as sodium acetate, potassium acetate, calcium acetate, and magnesium acetate; metal alkoxides such as sodium methoxide, sodium ethoxide, sodium tert-butoxide, potassium methoxide, and potassium tert-butoxide; metal hydroxides such as sodium hydroxide, potassium hydroxide, calcium hydroxide, and magnesium hydroxide; metal hydrides such as lithium hydride, sodium hydride, and calcium hydride, and mixtures of two or more of these. The amount of base used may be appropriately selected from the range of 0.5 to 10 mol per mol of the compound of formula [2], and is preferably 1.0 to 1.2 mol. The solvent that can be used in this step may be any solvent that does not inhibit the progress of this reaction, and examples thereof include nitriles such as acetonitrile; ethers such as diethyl ether, diisopropyl ether, tetrahydrofuran, dioxane, monoglyme, and diglyme; halogenated hydrocarbons such as dichloromethane, dichloroethane, chloroform, carbon tetrachloride, and tetrachloroethane; aromatic hydrocarbons such as benzene, chlorobenzene, nitrobenzene, and toluene; amides such as N,N-dimethylformamide and N,N-dimethylacetamide; imidazolinones such as 1,3-dimethyl-2-imidazolinone; sulfur compounds such as dimethyl sulfoxide; and a mixed solvent of two or more of these can also be used.The amount of solvent used may be appropriately selected from the range of 0.01 to 100 L per mole of the compound of formula [2], preferably 0.1 to 10 L. The reaction temperature may be selected from the range of -20°C to (the boiling point range of the inert solvent used), preferably 0°C to 100°C. The reaction may also be carried out using a phase transfer catalyst such as a quaternary ammonium salt. Examples of phase transfer catalysts include quaternary ammonium salts such as tetra-n-butylammonium bromide and benzyltriethylammonium bromide, 18-crown-6-ether, or a combination of two or more of these. When a phase transfer catalyst is used, the amount used may be appropriately selected from the range of 0.0001 to 1.0 mol per mole of the compound of formula [2], preferably 0.001 to 0.1 mol. The reaction time varies depending on the reaction temperature, reaction substrate, reaction amount, etc., but is usually 10 minutes to 48 hours. The compound of formula [4], which is the target of the reaction, is collected from the reaction system by a standard method after the reaction is completed, and can be purified by column chromatography, recrystallization, or the like, if necessary.

[0234] (Step 2) A compound represented by formula [4] can be reduced in a solvent to produce a compound represented by formula [5]. Reduction methods that can be used in this step include a method using a reducing agent such as zinc dust, reduced iron, tin powder, stannous chloride, or titanium chloride; a method using a hydrogen donor such as hydrazine in the presence of Raney nickel; catalytic hydrogen reduction in the presence of a catalyst such as Raney nickel, palladium on carbon, osmium on carbon, palladium hydroxide, or platinum oxide; or catalytic hydrogen transfer reduction. When a reducing agent is used in this step, the amount of the reducing agent used can be appropriately selected from the range of 0.05 to 10 mol, preferably 0.1 to 1.2 mol, per mol of the compound of formula [4]. Zinc dust or reduced iron can be preferably used as the reducing agent. When a hydrogen donor is used in this step, the amount of the hydrogen donor used can be appropriately selected from the range of 0.05 to 10 mol, preferably 0.1 to 1.2 mol, per mol of the compound of formula [4]. Hydrazine can be preferably used as the hydrogen donor. When a catalyst is used in this step, the amount of catalyst used may be appropriately selected from the range of 0.05 to 10 mol per mol of the compound of formula [4], preferably 0.1 to 1.2 mol. Raney nickel or palladium on carbon can be preferably used as the catalyst. Examples of solvents that can be used in this step include the same solvents as those described in Step 1. The amount of solvent used may be appropriately selected from the range of 0.01 to 100 L per mol of the compound of formula [4], preferably 0.1 to 10 L. The reaction temperature may be selected from the range of 0°C to (the boiling point range of the inert solvent used), preferably 0°C to 200°C. The reaction time varies depending on the reaction temperature, reaction substrate, reaction amount, etc., but can usually be 10 minutes to 48 hours. After completion of the reaction, the compound of formula [5], the target product of the reaction, is collected from the reaction system by a standard method and, if necessary, can be purified by column chromatography, recrystallization, or other procedures.

[0235] (Step 3) The compound represented by formula [5] is reacted with a compound represented by formula R １ SO ２ L １ Or (R １ SO２ ) ２ The compound of formula [6] can be produced by reacting a compound of formula R used in this step with a haloalkylsulfonyl derivative represented by formula [6] in a solvent in the presence or absence of a base. １ SO ２ L １ Or (R １ SO ２ ) ２ The amount of the haloalkylsulfonyl derivative represented by O used may be appropriately selected from the range of 0.5 to 10 moles per mole of the compound of formula [5], preferably 1.0 to 1.2 moles. Examples of solvents and bases that can be used in this step include the same compounds as those described in Step 1. The amount of the base used in this reaction may be appropriately selected from the range of 0 to 100 moles per mole of the compound of formula [5], preferably 0 to 10 moles. The amount of solvent used may be appropriately selected from the range of 0.01 to 100 L per mole of the compound of formula [5], preferably 0.1 to 10 L. The reaction temperature may be selected from the range of -78°C to (the boiling point range of the inert solvent used), preferably 0°C to 100°C. The reaction time varies depending on the reaction temperature, reaction substrate, reaction amount, etc., but can usually be 10 minutes to 48 hours. The compound of formula [6], the target product of the reaction, is collected from the reaction system by a standard method after completion of the reaction and, if necessary, can be purified by column chromatography, recrystallization, or other procedures.

[0236] (Step 4) The compound represented by formula [6] is treated with a compound represented by formula R ２ L １ The compound represented by formula [1] can be produced by reacting a compound represented by formula R ２ L １The amount of the compound represented by the formula (I) used may be appropriately selected from the range of 0.5 to 10 moles per mole of the compound of formula [6], preferably 1.0 to 1.2 moles. Examples of solvents and bases that can be used in this step include the same compounds as those described in Step 1. The amount of base used in this reaction may be appropriately selected from the range of 0 to 100 moles per mole of the compound of formula [6], preferably 0.1 to 10 moles. Furthermore, the amount of solvent used may be appropriately selected from the range of 0.01 to 100 L per mole of the compound of formula [6], preferably 0.1 to 10 L. The reaction temperature may be selected from the range of -20°C to (the boiling point range of the inert solvent used), preferably 0°C to 100°C. The reaction time varies depending on the reaction temperature, reaction substrate, reaction amount, etc., but is usually 10 minutes to 48 hours. The reaction can also be carried out using a phase transfer catalyst such as a quaternary ammonium salt. Examples of phase transfer catalysts include those similar to those described in Step 1. When a phase transfer catalyst is used, the amount used may be appropriately selected from the range of 0.0001 to 1.0 mol, preferably 0.001 to 0.1 mol, per mol of the compound of formula [6]. After completion of the reaction, the compound of formula [1], which is the target of the reaction, is collected from the reaction system by a standard method and can be purified, if necessary, by procedures such as column chromatography and recrystallization.

[0237] <Production Method 2> The compound represented by formula [1] can also be produced by a method consisting of the reaction scheme illustrated below.

[0238]

[0239] (In the formula, R １ , R ２ , R ３ , R ４ , A, E, W, X, Y, m, n, o, and p are as defined in formula [1] of (1) above, and L １ has the same meaning as above).

[0240] (Step 5) The compound represented by formula [5] is reacted with a compound represented by formula R ２ L １The compound represented by formula [7] can be produced by reacting a compound represented by formula R ２ L １ The amount of the compound represented by the formula (I) used may be appropriately selected from the range of 0.5 to 10 moles per mole of the compound of formula [5], preferably 1.0 to 1.2 moles. Examples of solvents and bases that can be used in this step include the same compounds as those described in Step 1. The amount of the base used in this reaction may be appropriately selected from the range of 0 to 100 moles per mole of the compound of formula [5], preferably 0 to 10 moles. Furthermore, the amount of solvent used may be appropriately selected from the range of 0.01 to 100 L per mole of the compound of formula [5], preferably 0.1 to 10 L. The reaction temperature may be selected from the range of -78°C to (the boiling point range of the inert solvent used), preferably 0°C to 100°C. The reaction time varies depending on the reaction temperature, reaction substrate, reaction amount, etc., but is usually 10 minutes to 48 hours. The reaction can also be carried out using a phase transfer catalyst such as a quaternary ammonium salt. Examples of the phase transfer catalyst include quaternary ammonium salts such as tetra-n-butylammonium bromide and benzyltriethylammonium bromide, 18-crown-6-ether, and combinations of two or more of these. When a phase transfer catalyst is used, the amount used may be appropriately selected from the range of 0.0001 to 1.0 mol per mol of the compound of formula [5], and is preferably 0.001 to 0.1 mol. After completion of the reaction, the compound of formula [7], which is the target of the reaction, is collected from the reaction system by a standard method and can be purified, if necessary, by procedures such as column chromatography and recrystallization.

[0241] (Step 6) The compound represented by formula [7] is reacted with a compound represented by formula R １ SO ２ L １ Or (R １ SO ２ ) ２The compound represented by formula [1] can be produced by reacting a haloalkylsulfonyl derivative represented by formula R with a haloalkylsulfonyl derivative represented by formula [1] in a solvent in the presence of a base. １ SO ２ L １ Or (R １ SO ２ ) ２ The amount of the haloalkylsulfonyl derivative represented by O used may be appropriately selected from the range of 0.5 to 10 moles per mole of the compound of formula [7], preferably 1.0 to 1.2 moles. Examples of solvents and bases that can be used in this step include the same compounds as those described in Step 1. The amount of the base used in this reaction may be appropriately selected from the range of 0.01 to 100 moles per mole of the compound of formula [7], preferably 0.1 to 10 moles. The amount of solvent used may be appropriately selected from the range of 0.01 to 100 L per mole of the compound of formula [7], preferably 0.1 to 10 L. The reaction temperature may be selected from the range of -78°C to (the boiling point range of the inert solvent used), preferably 0°C to 100°C. The reaction time varies depending on the reaction temperature, reaction substrate, reaction amount, etc., but is usually 10 minutes to 48 hours. The compound of formula [1], which is the target of the reaction, is collected from the reaction system by a standard method after the reaction is completed, and can be purified by column chromatography, recrystallization, or the like, if necessary.

[0242] <Production Method 3> The compound represented by formula [6] can also be produced by a method consisting of the reaction scheme illustrated below.

[0243]

[0244] (In the formula, R １ , R ３ , R ４ , A, E, W, X, Y, m, n, o, and p are as defined in formula [1] of (1) above, and L １ has the same meaning as above, and Alk independently represents alkyl, for example, C １ ~C ６ represents alkyl).

[0245] (Step 7) The compound represented by formula [5] is reacted with a compound represented by formula R １ SO ２ L １ Or (R １ SO ２ ) ２ The compound of formula [8] can be produced by reacting a compound of formula R used in this step with a haloalkylsulfonyl derivative represented by formula [8] in a solvent in the presence or absence of a base. １ SO ２ L １ Or (R １ SO ２ ) ２ The amount of the haloalkylsulfonyl derivative represented by O used may be appropriately selected from the range of 0.5 to 10 moles per mole of the compound of formula [5], preferably 1.0 to 1.2 moles. Examples of solvents and bases that can be used in this step include the same compounds as those described in Step 1. The amount of base used in this reaction may be appropriately selected from the range of 0 to 100 moles per mole of the compound of formula [5], preferably 0 to 10 moles. The amount of solvent used may be appropriately selected from the range of 0.01 to 100 L per mole of the compound of formula [5], preferably 0.1 to 10 L. The reaction temperature may be selected from the range of -78°C to (the boiling point range of the inert solvent used), preferably 0°C to 100°C. The reaction time varies depending on the reaction temperature, reaction substrate, reaction amount, etc., but can usually be 10 minutes to 48 hours. The compound of formula [8], the target product of the reaction, is collected from the reaction system by a standard method after completion of the reaction and can be purified, if necessary, by column chromatography, recrystallization, or other procedures.

[0246] (Step 8) The compound represented by formula [8] is reacted with a compound represented by formula Alk ４ The compound of formula [6] can be produced by reacting a compound of formula [6] with a compound of formula [6] represented by NOH or by hydrolysis using a base. Examples of solvents and bases that can be used in this step include the same as those described in step 1. ４Examples of the compound represented by NOH include tetramethylammonium hydroxide and tetrabutylammonium hydroxide. ４ The amount of the compound represented by NOH used may be appropriately selected from the range of 0 to 10 moles per mole of the compound of formula [8], preferably 0 to 2 moles, and more preferably 0.1 to 2 moles. The amount of the base used in this reaction may be appropriately selected from the range of 0 to 10 moles per mole of the compound of formula [8], preferably 0 to 2 moles, and more preferably 0.1 to 2 moles. The amount of the solvent used may be appropriately selected from the range of 0.01 to 100 L per mole of the compound of formula [8], preferably 0.1 to 10 L. The reaction temperature may be selected from the range of -20°C to (the boiling point range of the inert solvent used), preferably 0°C to 100°C. The reaction time varies depending on the reaction temperature, reaction substrate, reaction amount, etc., but can usually be 10 minutes to 48 hours. The compound of formula [6], the target product of the reaction, is collected from the reaction system by a standard method after completion of the reaction and can be purified, if necessary, by procedures such as column chromatography and recrystallization.

[0247] <Production Method 4> The compound represented by formula [6] can also be produced by a method consisting of the reaction scheme illustrated below.

[0248]

[0249] (In the formula, R １ , R ３ , R ４ , A, E, W, X, Y, m, n, o, and p are as defined in formula [1] of (1) above, and L １ has the same meaning as above).

[0250] (Step 9) The compound represented by formula [9] is reacted with a compound represented by formula R １ SO ２ L １ Or (R １ SO ２ ) ２The compound of formula

[10] can be produced by reacting a compound of formula R used in this step with a haloalkylsulfonyl derivative represented by formula

[10] in a solvent in the presence or absence of a base. １ SO ２ L １ Or (R １ SO ２ ) ２ The amount of the haloalkylsulfonyl derivative represented by O used may be appropriately selected from the range of 0.5 to 10 moles per mole of the compound of formula [9], preferably 1.0 to 1.2 moles. Examples of solvents and bases that can be used in this step include the same compounds as those described in Step 1. The amount of the base used in this reaction may be appropriately selected from the range of 0 to 100 moles per mole of the compound of formula [9], preferably 0 to 10 moles. The amount of solvent used may be appropriately selected from the range of 0.01 to 100 L per mole of the compound of formula [9], preferably 0.1 to 10 L. The reaction temperature may be selected from the range of -78°C to (the boiling point range of the inert solvent used), preferably 0°C to 100°C. The reaction time varies depending on the reaction temperature, reaction substrate, reaction amount, etc., but can usually be 10 minutes to 48 hours. The compound of formula

[10] , the target product of the reaction, is collected from the reaction system by a standard method after completion of the reaction and, if necessary, can be purified by column chromatography, recrystallization, or other procedures.

[0251] (Step 10) A compound represented by formula [6] can be produced by reacting a compound represented by formula

[10] with a compound represented by formula

[11] in a solvent in the presence of an acid. The amount of the compound represented by formula

[11] used in this step can be appropriately selected from the range of 0.5 to 10 moles per mole of the compound represented by formula

[10] , and is preferably 1.0 to 1.2 moles. Examples of acids that can be used in this step include organic acids such as formic acid, acetic acid, methanesulfonic acid, p-toluenesulfonic acid, trifluoroacetic acid, and trifluoromethanesulfonic acid; inorganic acids such as hydrochloric acid, sulfuric acid, and hydrogen bromide; Lewis acids such as zinc chloride, titanium tetrachloride, tin chloride, aluminum chloride, iron chloride, and boron trifluoride ether complex, and mixtures of two or more of these. The reaction can also be carried out using a phase-transfer catalyst such as a quaternary ammonium salt. Examples of phase-transfer catalysts include the same compounds as those described in Step 1. When a phase transfer catalyst is used, the amount used may be appropriately selected from the range of 0.0001 to 1.0 mol per mol of the compound of formula

[10] , preferably 0.001 to 0.1 mol. Examples of solvents that can be used in this step include the same compounds as those described in Step 1. The amount of acid used in this reaction may be appropriately selected from the range of 0.01 to 100 mol per mol of the compound of formula

[10] , preferably 0.1 to 10 mol. Furthermore, the amount of solvent used may be appropriately selected from the range of 0.01 to 100 L per mol of the compound of formula

[10] , preferably 0.1 to 10 L. The reaction temperature may be selected from the range of 0°C to (the boiling point range of the inert solvent used), preferably 0°C to 100°C. The reaction time varies depending on the reaction temperature, reaction substrate, reaction amount, etc., but is usually 10 minutes to 72 hours. The compound of formula [6], which is the target of the reaction, is collected from the reaction system by a standard method after the reaction is completed, and can be purified by column chromatography, recrystallization, or the like, if necessary.

[0252] <Production Method 5> The compound represented by formula

[12] can be produced by a method represented by the reaction scheme shown below.

[0253]

[0254] (In the formula, R １ , R ３ , R ４ , A, E, W, X, Y, m, n, o, and p are as defined in formula [1] of (1) above).

[0255] (Step 11) A compound represented by formula [6] can be reacted with a sulfurizing agent in a solvent to produce a compound represented by formula

[12] . Examples of sulfurizing agents that can be used in this step include P ４ S ８ , Lawesson's reagent, etc. The amount of sulfurizing agent used in this step may be appropriately selected from the range of 0.05 to 10 mol per mol of the compound of formula [6], preferably 0.1 to 1.2 mol. Examples of solvents that can be used in this step include the same compounds as those described in Step 1. The amount of solvent used may be appropriately selected from the range of 0.01 to 100 L per mol of the compound of formula [6], preferably 0.1 to 10 L. The reaction temperature may be selected from the range of -20°C to (the boiling point range of the inert solvent used), preferably 0°C to 100°C. The reaction time varies depending on the reaction temperature, reaction substrate, reaction amount, etc., but can usually be 10 minutes to 48 hours. After completion of the reaction, the compound of formula

[12] , the target product of the reaction, is collected from the reaction system by a standard method and, if necessary, can be purified by column chromatography, recrystallization, etc.

[0256] <Intermediate Production Method 1> The intermediate compound represented by formula [3a] can be produced by a method represented by the reaction scheme shown below.

[0257]

[0258] (In the formula, X １ , X ２ , X ３ and X ４ are as defined in the above formula (1) [1]).

[0259] (Step 12) A compound represented by formula [3a] can be produced by reacting a compound represented by formula

[13] with a diazotization reagent in a solvent in the presence of an acid. Examples of diazotization reagents that can be used in this step include t-butyl nitrite, sodium nitrite, or a combination thereof. The amount of the diazotization agent used in this step can be appropriately selected from the range of 0.05 to 10 mol per mol of the compound of formula

[13] , preferably 0.1 to 1.2 mol. Solvents that can be used in this step include the same solvents as those described in Step 1. Acids that can be used in this step include organic acids such as formic acid, acetic acid, glacial acetic acid, methanesulfonic acid, p-toluenesulfonic acid, trifluoroacetic acid, and trifluoromethanesulfonic acid, or mixtures thereof. The amount of the acid used in this reaction can be appropriately selected from the range of 0.01 to 100 mol per mol of the compound of formula

[13] , preferably 0.1 to 10 mol. The amount of solvent used may be appropriately selected from the range of 0.01 to 100 L per mole of the compound of formula

[13] , and is preferably 0.1 to 10 L. The reaction temperature may be selected from the range of -20°C to the boiling point range of the inert solvent used, and is preferably in the range of 0°C to 100°C. The reaction time varies depending on the reaction temperature, reaction substrate, reaction amount, etc., but can usually be 10 minutes to 48 hours. After completion of the reaction, the compound of formula [3a], which is the target of the reaction, is collected from the reaction system by a standard method and can be purified, if necessary, by procedures such as column chromatography and recrystallization.

[0260] <Intermediate Production Method 2> The intermediate compound represented by formula [3b] can be produced by a method represented by the reaction scheme shown below.

[0261]

[0262] (In the formula, R ８ is C such as methyl, ethyl, etc. １ ~C ６ Alkyl, phenyl, or Z ２A, X, Z, and o are each as defined in formula [1] of (1) above, and L ２ represents a halogen atom such as a chlorine atom or a bromine atom). (Step 13) A compound represented by formula

[15] can be produced by reacting a compound represented by formula

[14] with a halogenating reagent in a solvent. Examples of halogenating reagents that can be used in this step include chlorinating reagents such as chlorine, sulfuryl chloride, and N-chlorosuccinimide; brominating reagents such as bromine and N-bromosuccinimide; and mixtures of two or more of these compounds. The amount of halogenating reagent used in this step can be appropriately selected from the range of 0.05 to 10 mol per mol of the compound of formula

[14] , preferably 0.1 to 1.2 mol. Examples of solvents that can be used in this step include the same solvents as those described in Step 1. The amount of solvent used can be appropriately selected from the range of 0.01 to 100 L per mol of the compound of formula

[14] , preferably 0.1 to 10 L. The reaction temperature can be selected from the range of -20°C to the boiling point range of the inert solvent used, preferably 0°C to 100°C. The reaction time varies depending on the reaction temperature, reaction substrate, reaction amount, etc., but can usually be 10 minutes to 48 hours. After the reaction is completed, the target compound of the reaction, the compound of formula

[15] , is collected from the reaction system by a standard method, and can be purified, if necessary, by procedures such as column chromatography and recrystallization.

[0263] (Step 14) A compound represented by formula [3b] can be produced by reacting a compound represented by formula

[15] with an ammonia reagent in a solvent. Examples of the ammonia reagent that can be used in this step include aqueous ammonia. The amount of the ammonia reagent used in this step can be appropriately selected from the range of 0.05 to 10 mol per mol of the compound of formula

[15] , preferably 0.1 to 1.2 mol. Examples of solvents that can be used in this step include the same solvents as those described in Step 1. The amount of solvent used can be appropriately selected from the range of 0.01 to 100 L per mol of the compound of formula

[15] , preferably 0.1 to 10 L. The reaction temperature can be selected from the range of -20°C to the boiling point range of the inert solvent used, preferably 0°C to 100°C. The reaction time varies depending on the reaction temperature, reaction substrate, reaction amount, etc., but can usually be 10 minutes to 48 hours. The compound of formula [3b], which is the target of the reaction, is collected from the reaction system by a standard method after the reaction is completed, and can be purified by column chromatography, recrystallization, or the like, if necessary.

[0264] <Intermediate Production Method 3> The intermediate compound represented by formula [3c] can be produced by a method represented by the reaction scheme shown below.

[0265]

[0266] (In the formula, A, X, Z, and o are as defined in formula [1] of (1) above, and L １ and R ８ has the same meaning as above, and q represents 1 or 2).

[0267] (Step 15) The compound represented by formula

[16] is reacted with a compound represented by formula R ８ OC(O)L or (R ８ O.C. (O) ２ The compound of formula

[17] can be produced by reacting a compound of formula R used in this step with an alkoxycarbonyl derivative, a phenoxycarbonyl derivative, or a substituted phenoxycarbonyl derivative represented by formula

[18] in a solvent in the presence / absence of a base. ８OC(O)L or (R ８ O.C. (O) ２ The amount of the alkoxycarbonyl derivative, phenoxycarbonyl derivative, or substituted phenoxycarbonyl derivative represented by O used may be appropriately selected from the range of 0.5 to 10 moles per mole of the compound of formula

[16] , preferably 1.0 to 1.2 moles. Examples of solvents and bases that can be used in this step include the same compounds as those described in Step 1. The amount of the base used in this reaction may be appropriately selected from the range of 0 to 100 moles per mole of the compound of formula

[16] , preferably 0 to 10 moles. The amount of solvent used may be appropriately selected from the range of 0.01 to 100 L per mole of the compound of formula

[16] , preferably 0.1 to 10 L. The reaction temperature may be selected from the range of -78°C to the boiling point range of the inert solvent used, preferably 0°C to 100°C. The reaction time varies depending on the reaction temperature, reaction substrate, reaction amount, etc., but is usually 10 minutes to 48 hours. The compound of formula

[17] , which is the target of the reaction, is collected from the reaction system by a standard method after the reaction is completed, and can be purified by column chromatography, recrystallization, or the like, if necessary.

[0268] (Step 16) A compound represented by formula [3c] can be produced by reacting a compound represented by formula

[17] in a solvent in the presence of an acid. Examples of acids that can be used in this step include organic acids such as formic acid, acetic acid, methanesulfonic acid, p-toluenesulfonic acid, trifluoroacetic acid, and trifluoromethanesulfonic acid; inorganic acids such as hydrochloric acid, sulfuric acid, and hydrogen bromide; Lewis acids such as zinc chloride, titanium tetrachloride, tin chloride, aluminum chloride, iron chloride, and boron trifluoride ether complex; and mixtures of two or more of these compounds. The reaction can also be carried out using a phase transfer catalyst such as a quaternary ammonium salt. Examples of phase transfer catalysts include those similar to those described in Step 1. When a phase transfer catalyst is used, the amount used may be appropriately selected from the range of 0.0001 to 1.0 mol per 1 mol of the compound represented by formula

[17] , preferably 0.001 to 0.1 mol. Examples of solvents that can be used in this step include those similar to those described in Step 1. The amount of acid used in this reaction may be appropriately selected from the range of 0.01 to 100 mol per mole of the compound of formula

[17] , preferably 0.1 to 10 mol. The amount of solvent used may be appropriately selected from the range of 0.01 to 100 L per mole of the compound of formula

[17] , preferably 0.1 to 10 L. The reaction temperature may be selected from the range of 0°C to the boiling point range of the inert solvent used, preferably 0°C to 100°C. The reaction time varies depending on the reaction temperature, reaction substrate, reaction amount, etc., but can usually be 10 minutes to 72 hours. The compound of formula [3c], the target product of the reaction, is collected from the reaction system by a standard method after completion of the reaction and can be purified, if necessary, by procedures such as column chromatography and recrystallization.

[0269] <Intermediate Production Method 4> The intermediate compound represented by formula [5a] can be produced by a method represented by the reaction scheme shown below.

[0270]

[0271] (In the formula, R １ , R ３ , R ４ , X１ , X ２ , X ３ , X ４ , Y and p are as defined in formula [1] of (1) above).

[0272] (Step 17) A compound represented by formula

[18] and a compound represented by formula

[19] are reacted in a solvent to produce a compound represented by formula

[20] . The amount of the compound represented by formula

[19] used in this step may be appropriately selected from the range of 0.5 to 10 mol per mol of the compound represented by formula

[18] , preferably 1.0 to 1.2 mol. Examples of solvents that can be used in this step include the same solvents as those described in Step 1. The amount of solvent used may be appropriately selected from the range of 0.01 to 100 L per mol of the compound represented by formula

[18] , preferably 0.1 to 10 L. The reaction temperature may be selected from the range from 0°C to the boiling point range of the inert solvent used, preferably 0°C to 100°C. The reaction time varies depending on the reaction temperature, reaction substrate, reaction amount, etc., but is usually 10 minutes to 72 hours. The compound of formula

[20] , which is the target of the reaction, is collected from the reaction system by a standard method after the reaction is completed, and can be purified by column chromatography, recrystallization, or the like, if necessary.

[0273] (Step 18) A compound represented by formula

[21] can be produced by reacting a compound represented by formula

[20] with a diazotization reagent in a solvent in the presence of an acid. Examples of diazotization reagents that can be used in this step include t-butyl nitrite, sodium nitrite, or a mixture thereof. The amount of the diazotization agent used in this step can be appropriately selected from the range of 0.05 to 10 mol per mol of the compound of formula

[20] , preferably 0.1 to 1.2 mol. Solvents that can be used in this step include the same solvents as those described in Step 1. Acids that can be used in this step include organic acids such as formic acid, acetic acid, glacial acetic acid, methanesulfonic acid, p-toluenesulfonic acid, trifluoroacetic acid, and trifluoromethanesulfonic acid, or a mixture of two or more of these. The amount of the acid used in this reaction can be appropriately selected from the range of 0.01 to 100 mol per mol of the compound of formula

[20] , preferably 0.1 to 10 mol. The amount of solvent used may be appropriately selected from the range of 0.01 to 100 L per mole of the compound of formula

[20] , and preferably 0.1 to 10 L. The reaction temperature may be selected from the range of -20°C to the boiling point range of the inert solvent used, and is preferably performed in the range of 0°C to 100°C. The reaction time varies depending on the reaction temperature, reaction substrate, reaction amount, etc., but can usually be 10 minutes to 48 hours. After completion of the reaction, the compound of formula

[21] , which is the target of the reaction, is collected from the reaction system by a standard method and can be purified, if necessary, by procedures such as column chromatography and recrystallization.

[0274] (Step 19) A compound represented by formula [5a] can be produced by reacting a compound represented by formula

[21] in a solvent in the presence of an acid. Examples of solvents and acids that can be used in this step include those described in Steps 1 and 10. The amount of acid used in this reaction can be appropriately selected from the range of 0.01 to 100 mol per mole of the compound of formula

[21] , preferably 0.1 to 10 mol. The amount of solvent used can be appropriately selected from the range of 0.01 to 100 L per mole of the compound of formula

[21] , preferably 0.1 to 10 L. The reaction temperature can be selected from the range of 0°C to the boiling point of the inert solvent used, preferably 0°C to 100°C. The reaction time varies depending on the reaction temperature, reaction substrate, reaction amount, etc., but can usually be 10 minutes to 72 hours. The compound of formula [5a], the target product of the reaction, is collected from the reaction system by a standard method after completion of the reaction and can be purified, if necessary, by procedures such as column chromatography or recrystallization.

[0275] The amine protecting group may be any group that does not inhibit the sulfurization reaction, and the use, selection, and deprotection of the protecting group will be obvious to those skilled in the art of chemical synthesis (see, for example, T. W. Greene and P. G. Wuts, Protective Groups in Organic Synthesis, 4th Edition; Wiley: New York, 2007). It is anticipated that some of the reagents and reaction conditions described above for preparing compounds of formula [1] may not be compatible with specific functional groups present in intermediates. In these cases, the desired product can be obtained by incorporating protection / deprotection techniques or functional group interconversions into the synthesis. The use and choice of protecting groups will be apparent to those skilled in the art of chemical synthesis (see, for example, T. W. Greene and P. G. Wuts, Protective Groups in Organic Synthesis, 4th Edition; Wiley: New York, 2007). Those skilled in the art will recognize that, in some cases, after introducing certain reagents as illustrated in the individual schemes, additional routine synthetic steps not illustrated may be required to complete the synthesis of compounds of formula [1]. Those skilled in the art will also recognize that it may be necessary to perform combinations of the steps illustrated in the above schemes in an order other than the specific order proposed to prepare compounds of formula [1].

[0276] By using the techniques described herein in combination with methods known in the art, the compounds shown below can be prepared.

[0277]

[0278]

[0279]

[0280]

[0281] U is expressed by the following formula (22):

[0282]

[0283]

[0284]

[0285]

[0286]

[0287]

[0288]

[0289]

[0290]

[0291]

[0292]

[0293]

[0294]

[0295]

[0296]

[0297]

[0298]

[0299]

[0300]

[0301]

[0302]

[0303]

[0304]

[0305]

[0306]

[0307]

[0308]

[0309]

[0310]

[0311]

[0312]

[0313]

[0314]

[0315]

[0316]

[0317]

[0318]

[0319]

[0320]

[0321]

[0322]

[0323]

[0324]

[0325]

[0326]

[0327]

[0328]

[0329]

[0330]

[0331]

[0332]

[0333]

[0334]

[0335]

[0336]

[0337]

[0338]

[0339]

[0340]

[0341]

[0342]

[0343]

[0344]

[0345]

[0346]

[0347]

[0348] U is the same as in formula (22). In the table, Het-1 to Het-58 are each represented by the following structures.

[0349]

[0350]

[0351]

[0352]

[0353]

[0354]

[0355]

[0356]

[0357]

[0358]

[0359]

[0360]

[0361]

[0362]

[0363]

[0364]

[0365]

[0366]

[0367]

[0368]

[0369]

[0370]

[0371]

[0372]

[0373]

[0374]

[0375]

[0376]

[0377] More specifically,

[0378]

[0379] U is expressed by the following formula (23):

[0380]

[0381]

[0382]

[0383]

[0384]

[0385]

[0386]

[0387]

[0388]

[0389]

[0390]

[0391]

[0392]

[0393]

[0394]

[0395]

[0396]

[0397]

[0398]

[0399]

[0400]

[0401]

[0402]

[0403]

[0404]

[0405]

[0406]

[0407]

[0408]

[0409]

[0410]

[0411]

[0412]

[0413]

[0414]

[0415]

[0416]

[0417]

[0418]

[0419]

[0420]

[0421]

[0422]

[0423]

[0424]

[0425]

[0426]

[0427]

[0428]

[0429]

[0430]

[0431]

[0432]

[0433]

[0434]

[0435]

[0436]

[0437]

[0438]

[0439]

[0440]

[0441]

[0442]

[0443] U is the same as in the above formula (23).

[0444]

[0445]

[0446]

[0447]

[0448]

[0449]

[0450]

[0451]

[0452]

[0453]

[0454]

[0455]

[0456] The at least one agricultural and horticultural herbicide of component (b) is not particularly limited, and may contain or consist of one or more selected from the group consisting of ALS inhibitors, germination / elongation inhibitors, photosynthesis inhibitors, PPO inhibitors, bleaching agents, VLCFAs inhibitors, hormone action inhibitors / disruptors, and ACCase inhibitors.

[0457] The ALS inhibitor is not particularly limited, and examples thereof include amidosulfuron, azimsulfuron, bensulfuron-methyl, bispyribac, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cloransulam-methyl, and cyclosulfamuron. n), diclosulam, ethametsulfuron-methyl, ethoxysulfuron, flazasulfuron, florasulam, flucarbazone, flumetsulam, flupyrsulfuron-methyl, foramsulfuron, halosulfuron-methyl Iodosulfuron-methyl), imazamethabenzmethyl, imazamox, imazapic, imazapyr, imazaquin, imazethapyr, imazosulfuron, iodosulfuron-methyl, iofensulfuron, iofensulfuron sodium n-sodium), metazosulfuron, metsulfuron-methyl, nicosulfuron, orthosulfamuron, oxasulfuron, penoxsulam, primisulfuron-methyl, propoxycarbazone, propyrisulfuron,Prosulfuron, pyrazosulfuron-ethyl, pyribenzoxim, pyriftalid, pyriminobac-methyl, pyrimisulfan, pyrithiobac, rimsulfuron, sulfometuron-methyl, sulfosulfuron, thiencarbazone-methyl The compound may comprise or consist of one or more selected from the group consisting of thiencarbazone-methyl, thifensulfuron-methyl, triafamone, triasulfuron, tribenuron-methyl, trifloxysulfuron, triflusulfuron-methyl, and tritosulfuron. Among these, preferably, the ALS inhibitor may comprise or consist of one or more selected from the group consisting of bispyribac (hereinafter referred to as compound (1)), metazosulfuron (hereinafter referred to as compound (2)), penoxsulam (hereinafter referred to as compound (3)), pyrimisulfan (hereinafter referred to as compound (4)), propyrisulfuron (hereinafter referred to as compound (5)), sulfometuron-methyl (hereinafter referred to as compound (6)), and triafamone (hereinafter referred to as compound (7)).

[0458] The germination and elongation inhibitor is not particularly limited, and examples thereof include benfluralin, bromobutide, butamifos, butralin, carbetamide, chlorpropham, chlorthal-dimethyl, cumyluron, dichlobenil, dinitramine, and dithiopyr. , dymron, ethalfluralin, etobenzanide, methiozolin, methyldymron, oryzalin, oxaziclomefone, pendimethalin, propham, propyzamide, pyributicarb, sodium chlorate The composition may comprise or consist of one or more selected from the group consisting of tetrafluromethorphan chlorate, tetflupyrolimet, thiazopyr, triaziflam, and trifluralin. Among these, preferably, the germination and elongation inhibitor may comprise or consist of one or more selected from the group consisting of bromobutide (hereinafter referred to as compound (8)), dymron (hereinafter referred to as compound (9)), methiozolin (hereinafter referred to as compound (10)), sodium chlorate (hereinafter referred to as compound (11)), tetflupyrolimet (hereinafter referred to as compound (12)), and triaziflam (hereinafter referred to as compound (13)). More preferably, component (b) or the germination and elongation inhibitor may comprise or consist of dymron.

[0459] The photosynthesis inhibitor is not particularly limited, and examples thereof include ametryn, atrazine, bentazon, bromacil, bromoxynil, bromofenoxim, chlorbromuron, chloridazon, chlorotoluron, chloroxuron, cyanazine, desmedipham, desmedipham, desmetryn, dimefuron, dimethametryn, diuron, ethidimuron, fenuron, fluometuron, hexazinone, ioxynil, isoproturon, isouron, carbutilate, lenacil Lenacil, linuron, metamitron, methabenzthiazuron, metobromuron, metoxuron, metribuzin, monolinuron, neburon, pentanochlor, phenmedipham, prometon, prometryn ometryn), propanil, propazine, pyridafol, pyridate, quinoclamine, siduron, simazine, simetryn, tebuthiuron, terbacil, terbumeton, terbuthylazine, terbutryn,and trietazine. Among these, preferably, the photosynthesis inhibitor may comprise or consist of one or more selected from the group consisting of bentazone (hereinafter referred to as compound (14)), carbutilate (hereinafter referred to as compound (15)), and propanil (hereinafter referred to as compound (16)).

[0460] The PPO inhibitor is not particularly limited, and examples thereof include acifluorfen, azafenidin, benzfendizone, bifenox, butafenacil, carfentrazone-ethyl, and chloromethoxyfen. , chlorphthalim, cinidon-ethyl, cyclopyranil, fluazolate, flufenpyr-ethyl, flumiclorac-pentyl, flumioxazin, fluoroglycofenethyl fluoroglycofen-ethyl, fluthiacet-methyl, fomesafen, halosafen, lactofen, oxadiazon, oxadiargyl, oxyfluorfen, pentoxazone The antiviral composition may comprise or consist of one or more compounds selected from the group consisting of toxazone, profluazol, pyraclonil, pyraflufen-ethyl, saflufenacil, sulfentrazone, and thidiazimin. Among these, preferably, the PPO inhibitor may comprise or consist of one or more selected from the group consisting of carfentrazone-ethyl (hereinafter referred to as compound (17)), cyclopyranil (hereinafter referred to as compound (18)), oxadiargyl (hereinafter referred to as compound (19)), pentoxazone (hereinafter referred to as compound (20)), and pyraclonil (hereinafter referred to as compound (21)).

[0461] The whitening agent is not particularly limited, and examples thereof include aclonifen, amitrole, beflubutamid, benzobicyclon, benzofenap, bicyclopyrone, clomazone, cyclopyrimorate, diflufenican, fenquinotrione, fluridone, flurochloridone, and flurtamone. The antiviral composition may comprise or consist of one or more compounds selected from the group consisting of benzophenone-3, benzotriazole-3, benzotriazole-4, benzotriazole-5, benzotriazole-6, benzotriazole-7, benzotriazole-8, benzotriazole-9, benzotriazole-10, benzotriazole-11, benzotriazole-12, benzotriazole-13, benzotriazole-14, benzotriazole-15, benzotriazole-16, benzotriazole-17, benzotriazole-18, benzotriazole-19, benzotriazole-20, benzotriazole-21, benzotriazole-22, benzotriazole-23, benzotriazole-24, benzotriazole-25, benzotriazole-26, benzotriazole-27, benzotriazole-28, benzotriazole-29, benzotriazole-30, benzotriazole-31, benzotriazole-32, benzotriazole-33, benzotriazole-34, benzotriazole-35, benzotriazole-36, benzotriazole-37, benzotriazole-38, benzotriazole-41, benzotriazole-42, benzotriazole-43, benzotriazole-44, benzotriazole-45, benzotriazole-46, benzotriazole-47, benzotriazole-48, benzotriazole-49, benzotriazole-51, benzotriazole-52, benzotriazole-53, benzotriazole-54, benzotriazole-55, benzotriazole-55, benzotriazole-55, benzotriazole-56, benzotriazole-57, benzotriazole-58, benzotriazole-59, benzotriazole-59, benzotriazole-55, benzotriazole-55, benzotriazole-56, benzotriazole-57, benzotri Among these, preferably, the whitening agent may contain or consist of one or more selected from the group consisting of benzobicyclon (hereinafter referred to as compound (22)), clomazone (hereinafter referred to as compound (23)), cyclopyrimorate (hereinafter referred to as compound (24)), fenquinotrione (hereinafter referred to as compound (25)), iptriazopyrid (hereinafter referred to as compound (26)), mesotrione (hereinafter referred to as compound (27)), and tefuryltrione (hereinafter referred to as compound (28)).

[0462] The VLCFAs inhibitor is not particularly limited, and examples thereof include acetochlor, alachlor, anilofos, benfuresate, butachlor, butyrate, cafenstrole, dimepiperate, dimesulfazet, dimethachlor, dimethenamid, dimethenamid-P, EPTC, esprocarb, and the like. arb), ethofumesate, fenoxasulfone, fentrazamide, flufenacet, hexylthiocarbam, indanofan, ipfencarbazone, mefenacet, mefenacet, Metazachlor, molinate, orbencarb, pebulate, pethoxamid, piperophos, pretilachlor, propachlor, propisochlor, prosulfocarb The compound may comprise or consist of one or more selected from the group consisting of benzophenone, pyroxasulfone, S-metolachlor, thenylchlor, thiobencarb, thiocarbazil, triallate, and vernolate.Among these, preferably, the VLCFAs inhibitor may comprise or consist of one or more selected from the group consisting of benfuresate (hereinafter referred to as compound (29)), cafenstrole (hereinafter referred to as compound (30)), dimesulfazet (hereinafter referred to as compound (31)), fenoxasulfone (hereinafter referred to as compound (32)), fentrazamide (hereinafter referred to as compound (33)), ipfencarbazone (hereinafter referred to as compound (34)), and thenylchlor (hereinafter referred to as compound (35)).

[0463] The hormone action inhibitors / disruptors are not particularly limited, and examples thereof include 2,3,6-TBA, 2,4-D, 2,4-DB, 2,4-PA ethyl (2,4-PA-ethyl), aminocyclopyrachlor, aminopyralid, benazolin, chloramben, clomeprop, clopyralid, dicamba, dichlorprop, diflufenzopyr, florpyrauxifenbenzyl The compound may comprise or consist of one or more selected from the group consisting of hexafluoropropanediol, ... Among these, preferably, the hormone action inhibitor / disruptor can contain or consist of one or more selected from the group consisting of florpyrauxifen-benzyl (hereinafter referred to as compound (36)) and quinclorac (hereinafter referred to as compound (37)).

[0464] The ACCase inhibitor is not particularly limited, and examples thereof include alloxydim, butroxydim, clethodim, clodinafop-propargyl, cycloxydim, cyhalofop-butyl, diclofop-methyl, fenoxaprop-P-ethyl, fluazifop-P-butyl, haloxyfop-P- The active ingredient may comprise or consist of one or more selected from the group consisting of haloxyfop-P-methyl, metamifop, pinoxaden, profoxydim, propaquizafop, quizalofop-P-ethyl, sethoxydim, tepraloxydim, and tralkoxydim. Among these, preferably, the ACCase inhibitor may contain or consist of one or more selected from the group consisting of cyhalofop-butyl (hereinafter referred to as compound (38)) and metamifop (hereinafter referred to as compound (39)).

[0465] Examples of weeds that can be treated with the herbicidal composition of the present invention are listed below, but the present invention is not necessarily limited to these.

[0466] Various weeds that are a problem in farmland, such as polygonum species such as Polygonum orientalis, Rumex dock, Amaranth species such as Amaranth, Amaranth, and Amaranth, horseradish, nightshade, Chenopodium album, velvetleaf, American sedge, American hornwort, ragweed, corn poppy, morning glory, cocklebur, chickweed, chamomile, clematis, violets, persea buckthorn, linden grass, and crowfoot. It exhibits excellent herbicidal effects over a wide range of weeds from pre-germination to the growing season on broadleaf weeds such as field pea, field chrysanthemum, and shepherd's purse, as well as perennial and annual sedge weeds such as nutsedge, yellow nutsedge, Japanese sedge, sedge and sedge, and grass weeds such as barnyard grass, crabgrass, green foxtail, annual bluegrass, annual foxtail, Johnsongrass, black foxtail, ryegrass, and wild oats. It can also be used to control annual weeds that occur in paddy fields, such as barnyard grass, barnyard grass, cypress, Chinese laurel wattle, Japanese knotweed, Monochoria vaginalis, American dumbbell, dumbbell, Chinese laurel wattle, Chinese laurel, dwarf loosestrife, water chestnut, Japanese laurel, Japanese knotweed, Eastern chinaberry, water chestnut, Japanese knotweed, Eastern chinaberry, Eastern chinaberry, and Japanese holly, as well as perennial weeds, such as Sagittaria pygmaea, arrowhead, Cyperus serotinus, Euonymus kuroguwai, Bulbul, Arrowhead, Shizui, Siberian clubroot, pondweed, reed oak, Japanese knotweed, Japanese beangrass, and Japanese pine grove.

[0467] Furthermore, the herbicidal composition of the present invention is highly safe to useful plants and useful crops, such as cereals such as rice, wheat, barley, oats, rye, foxtail millet, millet, corn, and grain sorghum, as well as soybeans, cotton, sugar beets, sugarcane, onions, sunflowers, rapeseed, peanuts, flax, tobacco, coffee, sweet potatoes, potatoes, tomatoes, and other vegetables, or lawn grass. The useful plants and useful crops referred to here include so-called genetically modified crops such as corn, soybeans, cotton, rapeseed, and sugarcane that have been transformed by genetic technology and are resistant to herbicides, pests, and diseases, as well as plants that have been bred or selected to be resistant to herbicides, pests, and diseases. Examples of genetically modified plants are listed below, but are not necessarily limited to these.

[0468] Plants transformed to exhibit herbicide resistance, examples of which include glyphosate-resistant plants, bialaphos-resistant plants, bromoxynil-resistant plants, crops tolerant to sulfonylurea herbicides, crops tolerant to imidazolinone herbicides, 2,4-D-resistant plants, dicamba-resistant plants, isoxaflutole-resistant plants, and mesotrione-resistant plants.

[0469] Plants transformed to be resistant to pests, for example, plants transformed to produce Bt toxin (an insecticidal toxin of Bacillus thuringiensis), plants transformed to produce natural enemy attractants, etc.

[0470] Plants transformed to be resistant to plant diseases, such as virus-resistant plants and plants transformed to produce defensins. Plants transformed to extend the optimum harvest period and improve fruit storage, such as plants transformed to suppress polygalacturonase production and plants transformed to suppress ethylene biosynthesis enzymes.

[0471] Plants transformed to improve the safety of harvested products, such as plants that produce mycotoxin-degrading enzymes. Plants transformed to be useful for breeding, such as plants transformed to exhibit male sterility. Transformed plants that have been given traits useful as raw materials for bioethanol, such as plants that produce thermostable α-amylase.

[0472] Plants that have been transformed to exhibit tolerance to environmental stresses, for example, plants that exhibit drought tolerance by utilizing RNA chaperones, plants that accumulate glycine betaine, a compatible solute found in large quantities in cold-tolerant plants, plants that accumulate proline, a compatible solute, plants that accumulate trehalose, which has strong water-retaining properties, and exhibit drought tolerance, plants that overproduce enzymes that eliminate active oxygen, plants that exhibit tolerance to iron deficiency in alkaline soil by producing mugineic acids, and plants that exhibit tolerance to iron deficiency by producing mugineic acids.

[0473] Plants that have been transformed to produce specific functional nutrients, such as plants that overproduce oleic acid, plants that overproduce stearidonic acid, plants that overproduce lysine, provitamin A-enriched crops, vitamin E-enriched plants, plants that overproduce anthocyanins, and plants that produce cedar allergens and have the effect of alleviating cedar pollen allergies.

[0474] To control weeds, the herbicidal composition of the present invention can be used in an amount adjusted to be effective against weeds but not toxic to useful plants and useful crops. Here, an amount that is effective but not toxic to useful plants and useful crops means an amount that can sufficiently control weeds but does not harm useful plants and useful crops, and this amount can vary within a relatively wide range depending on the weeds to be controlled, the plants to which it is applied, the natural environment in which it is used, and the components of the composition of the present invention.

[0475] The herbicidal composition of the present invention can be used to control weeds by treating all plants or plant parts, as well as the soil surrounding plants, or the soil where seeds are sown, rice paddies, hydroponic water, and growing materials, with the herbicidal composition of the present invention by spraying, dusting, dusting, spraying, diffusing, immersing, irrigating, injecting, watering (dipping), foaming, applying, dusting, coating, spraying, fumigating, smoking, misting, or painting. Here, "all plants" refers to plants or groups of plants, such as wild plants, cultivated plants, naturally occurring plants, and cultivated plants, and also includes plants produced by breeding methods such as introduction breeding, isolation breeding, cross breeding, heterosis breeding, mutation breeding, polyploid breeding, genetic recombination (gene introduction), and marker-assisted selection. When the herbicidal composition of the present invention is applied to control weeds, the treatment can be carried out before or throughout the growth period of useful plants and useful crops, regardless of whether weeds emerge or not. Here, "plant parts" refers to all parts of a plant, such as leaves, stems, trunks, branches, flowers, fruiting bodies, fruits, seeds, roots, tubers, and rhizomes, or a combination thereof. When the herbicidal composition of the present invention is applied to control weeds, the application can be carried out in agricultural or non-agricultural land. Agricultural land is not particularly limited, and may be a field, paddy field, mountain forest, orchard, floriculture land, or lawn cultivation land. Non-agricultural land is not particularly limited, and may be a parking lot, cemetery, railway, or road.

[0476] The herbicidal composition of the present invention may contain additives commonly used in pesticide formulations, if necessary. Examples of such additives include carriers such as solid or liquid carriers, surfactants, binders, tackifiers, thickeners, colorants, spreaders, antifreeze agents, anticaking agents, disintegrants, and antidecomposition agents. If necessary, preservatives, plant fragments, and the like may also be used as additional components. These additives may be used alone or in combination of two or more.

[0477] The additive components will now be described.

[0478] Examples of solid carriers include natural minerals such as quartz, clay, kaolinite, pyrophyllite, sericite, talc, chalk, bentonite, attapulgite, montmorillonite, acid clay, attapulgite, zeolite, natural rock, diatomaceous earth, calcite, marble, pumice, sepiolite, and dolomite, inorganic salts such as calcium carbonate, ammonium sulfate or other ammonium salts, sodium sulfate, calcium chloride, and potassium chloride, organic solid carriers such as synthetic silicic acid, synthetic silicates, alumina, finely divided silica, silicates, starch, cellulose, and plant powder, and plastic carriers such as polyethylene, polypropylene, and polyvinylidene chloride. These may be used alone or in combination of two or more.

[0479] Examples of liquid carriers include monohydric alcohols such as methanol, ethanol, propanol, i-propanol, and butanol; alcohols broadly classified into polyhydric alcohols such as ethylene glycol, diethylene glycol, propylene glycol, hexylene glycol, polyethylene glycol, polypropylene glycol, and glycerin; polyhydric alcohol derivatives such as propylene glycol ether; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, cyclohexanone, and isophorone; ethers such as ethyl ether, dioxane, cellosolve, dipropyl ether, and tetrahydrofuran; normal paraffin; naphthenic acid; Examples of suitable solvents include aliphatic hydrocarbons such as benzene, toluene, xylene, solvent naphtha, and alkylnaphthalenes, halogenated hydrocarbons such as dichloroethane, chloroform, and carbon tetrachloride, esters such as ethyl acetate, diisopropyl phthalate, dibutyl phthalate, dioctyl phthalate, and dimethyl adipate, lactones such as γ-butyrolactone, amides such as dimethylformamide, diethylformamide, dimethylacetamide, and N-alkylpyrrolidines, nitriles such as acetonitrile, sulfur compounds such as dimethyl sulfoxide, vegetable oils such as soybean oil, rapeseed oil, cottonseed oil, and castor oil, and water. These may be used alone or in combination of two or more.

[0480] The surfactant is not particularly limited, and examples thereof include sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters, sucrose fatty acid esters, polyoxyethylene fatty acid esters, polyoxyethylene resin acid esters, polyoxyethylene fatty acid diesters, polyoxyethylene alkyl ethers, polyoxyethylene alkylphenol ethers, polyoxyethylene dialkylphenyl ethers, polyoxyethylene alkylphenol formalin condensates, polyoxyethylene polyoxypropylene block polymers, alkyl polyoxyethylene polypropylene block polymer ethers, polyoxyethylene alkylamines, polyoxyethylene fatty acid amides, polyoxyethylene fatty acid bisphenyl ethers, polyalkylene benzyl phenyl ethers, polyoxyalkylene styrene phenyl ethers, acetylene diols, polyoxyalkylene-added acetylene diols, polyoxyethylene ether-type silicones, ester-type silicones, fluorine-based surfactants, polyoxyethylene castor oils, and the like. Examples of such surfactants include nonionic surfactants such as oil and polyoxyethylene hydrogenated castor oil, alkyl sulfates, polyoxyethylene alkyl ether sulfates, polyoxyethylene alkyl phenyl ether sulfates, alkyl benzene sulfonates, lignin sulfonates, alkyl sulfosuccinates, naphthalene sulfonates, alkyl naphthalene sulfonates, salts of formalin condensates of naphthalene sulfonic acid, salts of formalin condensates of alkyl naphthalene sulfonic acid, fatty acid salts, polycarboxylates, N-methyl-fatty acid sarcosinates, resin salts, polyoxyethylene alkyl ether phosphates, and anionic surfactants such as polyoxyethylene alkyl phenyl ether phosphates, cationic surfactants such as alkylamine salts such as laurylamine hydrochloride, stearylamine hydrochloride, oleylamine hydrochloride, stearylamine acetate, stearylaminopropylamine hydrochloride, alkyltrimethylammonium chloride, and alkyldimethylbenzalkonium chloride, and amphoteric surfactants such as amino acid or betaine types. These surfactants may be used alone or in combination of two or more.

[0481] Examples of binders and tackifiers include carboxymethylcellulose and its salts, dextrin, water-soluble starch, xanthan gum, guar gum, sucrose, polyvinylpyrrolidone, gum arabic, polyvinyl alcohol, polyvinyl acetate, sodium polyacrylate, polyethylene glycol with an average molecular weight of 6,000 to 20,000, polyethylene oxide with an average molecular weight of 100,000 to 5,000,000, and natural phospholipids (e.g., cephalic acid, lecithinic acid, etc.). These binders and tackifiers may be used alone or in combination of two or more. Examples of thickeners include xanthan gum, guar gum, carboxymethylcellulose, polyvinylpyrrolidone, carboxyvinyl polymers, acrylic polymers, starch derivatives, water-soluble polymers such as polysaccharides, high-purity bentonite, and inorganic fine powders such as white carbon. These thickeners may be used alone or in combination of two or more. Examples of colorants include inorganic pigments such as iron oxide, titanium oxide, and Prussian blue, and organic dyes such as alizarin dyes, azo dyes, and metal phthalocyanine dyes. These colorants may be used alone or in combination of two or more.

[0482] Examples of spreading agents include silicone surfactants, cellulose powder, dextrin, modified starch, polyaminocarboxylic acid chelate compounds, cross-linked polyvinylpyrrolidone, maleic acid and styrene acid copolymers, methacrylic acid copolymers, half esters of polyhydric alcohol polymers and dicarboxylic acid anhydrides, and water-soluble salts of polystyrene sulfonic acid. These spreading agents may be used alone or in combination of two or more. Examples of spreading agents include various surfactants such as sodium dialkyl sulfosuccinate, polyoxyethylene alkyl ethers, polyoxyethylene alkylphenyl ethers, and polyoxyethylene fatty acid esters, as well as paraffin, terpene, polyamide resins, polyacrylates, polyoxyethylene, wax, polyvinyl alkyl ethers, alkylphenol-formalin condensates, and synthetic resin emulsions. These spreading agents may be used alone or in combination of two or more.

[0483] Examples of the antifreezing agent include polyhydric alcohols such as ethylene glycol, diethylene glycol, propylene glycol, glycerin, etc. These antifreezing agents may be used alone or in combination of two or more.

[0484] Examples of anti-caking agents include starch, alginic acid, polysaccharides such as mannose and galactose, polyvinylpyrrolidone, white carbon, ester gum, and petroleum resins. These anti-caking agents may be used alone or in combination of two or more. Examples of disintegrants include sodium tripolyphosphate, sodium hexane metaphosphate, metal stearates, cellulose powder, dextrin, methacrylic acid ester copolymers, polyvinylpyrrolidone, polyaminocarboxylic acid chelate compounds, sulfonated styrene-isobutylene-maleic anhydride copolymers, and starch-polyacrylonitrile graft copolymers. These disintegrants may be used alone or in combination of two or more.

[0485] Examples of the anti-decomposition agent include desiccants such as zeolite, quicklime, and magnesium oxide, antioxidants such as phenols, amines, sulfurs, and phosphoric acids, and ultraviolet absorbers such as salicylic acid and benzophenones. These anti-decomposition agents may be used alone or in combination of two or more.

[0486] Examples of preservatives include potassium sorbate, 1,2-benzthiazolin-3-one, etc. These preservatives may be used alone or in combination of two or more.

[0487] Examples of plant debris include sawdust, coconut husks, corn cobs, tobacco stalks, and the like.

[0488] When the above-mentioned additive components are contained in the pesticide composition of the present invention, the content ratio thereof is selected from the range of usually 5 to 95%, preferably 20 to 90%, by mass, for the carrier, usually 0.1 to 30%, preferably 0.5 to 10%, for the surfactant, and 0.1 to 30%, preferably 0.5 to 10%, for the other additives.

[0489] The herbicide of the present invention can be used as a formulation suitable for herbicides such as liquid formulations, emulsifiable concentrates, wettable powders, dust formulations, oil formulations, water dispersible granules, flowable formulations, emulsion suspensions, granules, jumbo formulations, suspoemulsions, and bean-crushed (registered trademark) formulations.

[0490] Such an embodiment can be obtained by a conventional method of mixing at least one composition of the present invention with a suitable solid or liquid carrier, and, if desired, with suitable adjuvants (e.g., surfactants, solvents, stabilizers) for improving the dispersibility of the active ingredient or other properties. When used, the composition is diluted to an appropriate concentration and sprayed or applied directly.

[0491] The blending ratio of the composition of the present invention is appropriately selected as needed, but the amount of Compound A in the composition of the present invention is usually appropriately selected from the range of 0.001 to 50% (by weight), preferably 0.005 to 30% (by weight), when it is made into a dust or granule. When it is made into an emulsifiable concentrate or wettable powder, it is appropriately selected from the range of 1 to 50% (by weight), preferably 5 to 30% (by weight). When it is made into a flowable, it is appropriately selected from the range of 1 to 50% (by weight), preferably 2 to 30% (by weight).

[0492] The suitable mixing ratio of component (a): a compound represented by formula [1] or a salt thereof (compound A) and component (b): an agricultural and horticultural herbicide (compound B) in a herbicidal composition is preferably 0.01 to 100 parts by weight, more preferably 0.01 to 30 parts by weight, and most preferably 0.05 to 20 parts by weight of compound B relative to 1 part by weight of compound A.

[0493] The application rate of the herbicidal composition of the present invention varies depending on the type of compound used, the target crop, the target disease, the occurrence tendency, environmental conditions, the formulation used, etc., but when used as is as a dust or granule, the application rate should be appropriately selected from the range of 1 g to 50 kg, preferably 10 g to 10 kg, of the active ingredient per hectare. When used in liquid form, such as an emulsifiable concentrate, wettable powder or flowable formulation, the application rate should be appropriately selected from the range of 0.1 to 50,000 ppm, preferably 10 to 10,000 ppm.

[0494] The composition of the present invention may be mixed with other herbicides, various insecticides, fungicides, plant growth regulators or synergists when formulated or sprayed, if necessary.

[0495] In particular, by applying the compound in combination with other herbicides, costs can be reduced by reducing the amount of herbicide applied, and the synergistic effect of the mixed herbicides can be expected to broaden the herbicidal spectrum and achieve a higher herbicidal effect. In this case, it is also possible to combine the compound with multiple known herbicides at the same time. In the present invention, when applying the compound, each compound may be applied individually or as a mixed composition. When applying each compound individually, they may be applied simultaneously or separately if they are applied in close time intervals. Either case is included in the method of the present invention.

[0496] Next, the usefulness of the present invention will be specifically explained in the following test examples, although the present invention is not limited to these examples.

[0497] Those skilled in the art will recognize that various electrophilic, nucleophilic, radical, organometallic, oxidative, and reductive reactions can be carried out on the compounds of formula [1] and intermediates described herein to add or modify existing substituents. Without further elaboration, it is believed that those skilled in the art using the above description will be able to utilize the present invention to its fullest extent. Therefore, the following examples should be construed as merely illustrative and in no way limit the present disclosure. The steps in the following examples illustrate the procedures for each step in the overall synthetic development, and the starting materials for each step do not necessarily have to be prepared by carrying out the specific preparations described in other examples or steps. In the following description, "%" indicates percentage by weight, and "parts" indicates parts by weight.

[0498] Example 1 Preparation of N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-azabicyclo[4.2.0]octa-1(6),2,4-trien-8-one (Compound 1-1)

[0499] Step 1: Preparation of tert-butyl [2-[(2-aminobenzamido)methyl]phenyl]carbamate Isatoic anhydride (326 mg) and benzylamine (450 mg) were dissolved in tetrahydrofuran (20 mL) and stirred at 60°C for 8 hours. The reaction mixture was concentrated, and the residue was purified using a flash automatic purification system (Biotage AB / Isolera ＴＭ The residue was purified by flash chromatography on silica gel using a column chromatography column (eluted with ethyl acetate-hexane: 15%-60%) to give the title compound as a colorless resinous solid (378 mg, 55% yield).

[0500] Step 2: Preparation of N-[2-[N-(1,1-dimethyl-ethyl)oxycarbonyl]aminobenzyl]-7-azabicyclo[4.2.0]octa-1(6),2,4-trien-8-one The compound obtained in Step 1 of Example 1 above (370 mg) was dissolved in acetonitrile (15 mL), and tert-butyl nitrite (189 mg) and acetic acid (165 mg) were added, followed by stirring at room temperature for 3 hours. Water was added to the reaction solution, and after stirring, the precipitated solid was filtered, washed with water, and air-dried to obtain the title compound as a colorless resinous solid (320 mg, yield 90%).

[0501] Step 3: Preparation of N-(2-aminobenzyl)-7-azabicyclo[4.2.0]octa-1(6),2,4-trien-8-one. The compound obtained in Step 2 of Example 1 above (320 mg) was dissolved in dioxane (20 mL), and 4 N hydrochloric acid in dioxane (5 mL) was added, followed by stirring at room temperature for 20 hours. The precipitated solid was filtered, washed with ethyl acetate, and air-dried to obtain the title compound as a colorless resinous solid (200 mg, yield 77%).

[0502] Step 4: Preparation of N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-azabicyclo[4.2.0]octa-1(6),2,4-trien-8-one The compound obtained in Step 3 of Example 1 above (200 mg) was dissolved in dichloromethane (20 mL), and triethylamine (162 mg) and trifluoromethanesulfonic anhydride (226 mg) were added in an ice-water bath, followed by stirring at room temperature for 20 hours. The reaction solution was concentrated, dissolved in ethyl acetate, and then washed with 1N aqueous hydrochloric acid. The organic layer was dried over anhydrous sodium sulfate, and inorganic substances were filtered off. After the solvent was evaporated under reduced pressure, the residue was purified using a flash automatic purification system (Isolera, manufactured by Biotage AB). ＴＭ The residue was purified by silica gel flash chromatography on a 100% column (eluted with ethyl acetate-hexane: 10%-30%) to give the title compound as a colorless resinous solid (148 mg, 52% yield).

[0503] Example 2 Preparation of N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-chloro-1,3-dihydroisoindol-1-one (Compound 2-3)

[0504] Step 1: Preparation of methyl 2-bromomethyl-6-chlorobenzoate Methyl 2-chloro-6-methylbenzoate (1.4 g) (a compound described in WO 2010 / 108651), N-bromosuccinimide (1.42 g), and benzoyl peroxide (122 mg, 75%) were dissolved in carbon tetrachloride (25 mL) and heated under reflux for 16 hours. After cooling, the reaction mixture was filtered through Celite. The solvent was evaporated under reduced pressure, and the residue was purified using a flash automatic purification system (Biotage AB / Isolera ＴＭ The residue was purified by flash chromatography on silica gel using a HPLC system (eluted with ethyl acetate-hexane: 5%-15%) to give the title compound as a colorless oil (1.49 g, 75% yield).

[0505] Step 2: Preparation of 7-chloro-1,3-dihydroisoindol-1-one The compound obtained in Step 1 of Example 2 above (1.47 g) was dissolved in tetrahydrofuran (40 mL), and aqueous ammonia (20 mL) was added, followed by stirring at room temperature overnight. Water was added to the reaction solution, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous sodium sulfate, and inorganic matter was filtered off, after which the solvent was evaporated under reduced pressure. Dichloromethane and hexane were added to the residue, and the precipitated solid was filtered and air-dried to obtain the title compound as a pale yellow solid (820 mg, yield 88%).

[0506] Step 3: Preparation of N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-chloro-1,3-dihydroisoindol-1-one The compound obtained in Step 2 of Example 2 above (90 mg), 1,1,1-trifluoro-N-[2-(hydroxymethyl)phenyl]methanesulfonamide (115 mg) (a compound described in WO 2010 / 026989 ), and paratoluenesulfonic acid monohydrate (49 mg) were dissolved in orthodichlorobenzene (5 mL), and the resulting solution was heated in a microwave synthesizer (Initiator+, manufactured by Biotage AB). ＴＭ The reaction mixture was heated and stirred at 250°C for 5 minutes using a flash automatic purification device (Biotage AB / Isolera). ＴＭ The residue was purified by flash chromatography on silica gel using a column chromatography column (eluted with ethyl acetate-hexane: 15%-60%) to give the title compound as a pale yellow resinous solid (158 mg, 77% yield).

[0507] Example 3 Preparation of N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5-chloro-8-fluoro-3,4-dihydroisoquinolin-1(2H)-one (Compound 3-64)

[0508] Step 1: Preparation of 5-chloro-8-fluoro-3,4-dihydroisoquinolin-1(2H)-one 2-Chloro-5-fluorophenethylamine (900 mg) (a compound described in WO 2006 / 009054) and triethylamine (787 mg) were dissolved in dichloromethane (20 mL), and methyl chloroformate (712 mg) was added dropwise in an ice-water bath, followed by stirring at room temperature overnight. Water was added to the reaction solution, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous sodium sulfate, and inorganic matter was filtered off, after which the solvent was distilled off under reduced pressure. The residue was dissolved in trifluoromethanesulfonic acid (5 mL) and the resulting mixture was subjected to a microwave synthesis using a microwave synthesis apparatus (Biotage AB / Initiator+). ＴＭ The reaction mixture was heated and stirred at 160°C for 5 minutes using a centrifuge. The reaction mixture was added to ice water and extracted with dichloromethane. The organic layer was dried over anhydrous sodium sulfate, and inorganic substances were filtered off. The solvent was then distilled off under reduced pressure, and the residue was purified using a flash automatic purification apparatus (Isolera, manufactured by Biotage AB). ＴＭ The residue was purified by flash chromatography on silica gel using a HPLC system (eluted with ethyl acetate-hexane: 30%-60%) to give the title compound as a brown oil (290 mg, 28% yield).

[0509] Step 2: Preparation of N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5-chloro-8-fluoro-3,4-dihydroisoquinolin-1(2H)-one The compound obtained in Step 1 of Example 3 above (290 mg), 1,1,1-trifluoro-N-[2-(hydroxymethyl)phenyl]methanesulfonamide (327 mg) (a compound described in WO 2010 / 026989 ), and paratoluenesulfonic acid monohydrate (138 mg) were dissolved in orthodichlorobenzene (5 mL), and the resulting solution was heated in a microwave synthesizer (Biotage AB / Initiator+). ＴＭ The reaction mixture was heated and stirred at 250°C for 5 minutes using a flash automatic purification device (Biotage AB / Isolera). ＴＭ The residue was purified by flash chromatography on silica gel using a column chromatography column (eluted with ethyl acetate-hexane: 20%-70%) to give the title compound as a brown resinous solid (91 mg, 14% yield).

[0510] Example 4 Preparation of N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one (Compound 3-149)

[0511] Step 1: Preparation of dimethyl 2,2'-[carbonylbis(oxy)]dibenzoate Methyl salicylate (38.16 g) and triethylamine (64 mL) were dissolved in tetrahydrofuran (120 mL), and a solution of triphosgene (12.0 g) in dichloromethane (120 mL) was added dropwise in an ice-water bath, followed by stirring overnight at room temperature. A 0.5 N aqueous solution of hydrochloric acid was added to the reaction solution, and the mixture was extracted with dichloromethane. The extracted solution was dried over sodium sulfate and filtered, after which the organic solvent was evaporated under reduced pressure. Dichloromethane and hexane were added to the residue, and the precipitated solid was filtered and air-dried to obtain the title compound as a colorless solid (33.9 g, 85% yield).

[0512] Step 2: Preparation of methyl 2-[[(2,5-difluorophenethyl)carbamoyl]oxy]benzoate The compound obtained in Step 1 of Example 4 (20.9 g) and 2,5-difluorophenethylamine (9.9 g) (a compound described in WO 2000 / 073283) were dissolved in tetrahydrofuran (210 mL) and stirred overnight at room temperature. The reaction mixture was concentrated, and the residue was purified using a flash automatic purification apparatus (Biotage AB / Isolera ＴＭ The residue was purified by flash chromatography on silica gel using a HPLC system (eluted with ethyl acetate-hexane: 5%-30%) to give the title compound as a colorless solid (14.4 g, 68% yield).

[0513] Step 3: Preparation of 5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one The compound obtained in Step 2 of Example 4 above (14.4 g) was dissolved in dichloromethane (287 mL), and trifluoromethanesulfonic acid (50.6 mL) was added dropwise in an ice-water bath, followed by stirring at room temperature for 2 hours. The reaction solution was gradually added to the ice-water bath, and the aqueous layer was extracted with dichloromethane. The organic layer was dried over magnesium sulfate, and inorganic matter was removed by filtration, after which the solvent was evaporated under reduced pressure. The residue was washed with diethyl ether, filtered, and air-dried to obtain the title compound as a colorless solid (3.41 g, yield 43%).

[0514] Step 4: Preparation of N-(2-nitrobenzyl)-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one. The compound obtained in Step 3 of Example 4 above (2.18 g) was dissolved in N,N-dimethylformamide (15 mL), and sodium hydride (499.8 mg, 60%) was added in an ice-water bath. The mixture was then stirred at room temperature for 15 minutes. After cooling again in an ice-water bath, a solution of 2-nitrobenzyl bromide (3.86 g) in N,N-dimethylformamide (10 mL) was added dropwise, and the mixture was stirred at room temperature overnight. Water and 1 N aqueous hydrochloric acid were added to the reaction solution, and the mixture was extracted with ethyl acetate. The extracted solution was washed with saturated brine and dried over sodium sulfate. The inorganic matter was filtered off, and the solvent was then evaporated under reduced pressure. Dichloromethane and hexane were added to the residue, and the precipitated solid was filtered and air-dried to obtain the title compound as a pale yellow solid (3.08 g, 81% yield).

[0515] The compound obtained in Step 4 of Example 4 (3.08 g) and palladium on carbon (308 mg, 10%) were dissolved in ethyl acetate (39 mL) and stirred overnight at room temperature under a hydrogen atmosphere. The reaction mixture was filtered through Celite and washed with ethyl acetate, and the solvent was evaporated from the filtrate under reduced pressure to give the title compound as a colorless solid (2.77 g, yield 99%).

[0516] Step 6: Preparation of N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one The compound obtained in Step 5 of Example 4 above (250 mg) and triethylamine (132 mg) were dissolved in dichloromethane (8.7 mL), and trifluoromethanesulfonic anhydride (265 mg) was added dropwise at -78°C. The temperature was gradually raised to room temperature, and the mixture was stirred at room temperature overnight. Water and 1N aqueous hydrochloric acid were added to the reaction mixture, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous sodium sulfate, and inorganic substances were filtered off. After the solvent was distilled off under reduced pressure, the residue was purified using a flash automatic purification system (Biotage AB / Isolera ＴＭ The residue was purified by flash chromatography on silica gel using a column chromatography column (eluted with ethyl acetate-hexane: 5%-30%) to give the title compound as a colorless resinous solid (256 mg, 70% yield).

[0517] Step 7: Preparation of N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one The compound obtained in Step 6 of Example 4 above (173 mg), ethyl chloroformate (49 mg), and sodium bicarbonate (38 mg) were dissolved in acetonitrile (5 mL) and heated under reflux for 8 hours. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and the inorganic matter was filtered off. After the solvent was evaporated under reduced pressure, the residue was purified using a flash automatic purification system (Isolera, manufactured by Biotage AB). ＴＭ The residue was purified by silica gel flash chromatography on a 100% column (eluted with ethyl acetate-hexane: 10%-30%) to give the title compound as a colorless resinous solid (182 mg, 90% yield).

[0518] Example 5 Preparation of N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-8-fluoro-5-methyl-3,4-dihydroisoquinolin-1(2H)-one (Compound 3-151)

[0519] Step 1: Preparation of methyl (5-fluoro-2-methylphenethyl)carbamate 5-Fluoro-2-methylphenethylamine (1.62 g) (a compound described in WO 2005 / 090287) and triethylamine (1.6 g) were dissolved in dichloromethane (30 mL), and methyl chloroformate (1.2 g) was added dropwise in an ice-water bath, followed by stirring overnight at room temperature. Water was added to the reaction solution, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous sodium sulfate, and inorganic substances were filtered off. After the solvent was distilled off under reduced pressure, the residue was purified using a flash automatic purification system (Biotage AB / Isolera ＴＭ The residue was purified by flash chromatography on silica gel using a HPLC column (eluted with ethyl acetate-hexane: 5%-20%) to give the title compound as a brown oil (1.49 g, 67% yield).

[0520] Step 2: Preparation of 8-fluoro-5-methyl-3,4-dihydroisoquinolin-1(2H)-one The compound obtained in Step 1 of Example 5 (1.0 g) was dissolved in trifluoromethanesulfonic acid (5 mL), and the resulting solution was heated in a microwave synthesizer (Initiator+, manufactured by Biotage AB). ＴＭ The reaction mixture was heated and stirred at 160°C for 8 minutes using a centrifuge. The reaction mixture was added to ice water and extracted with dichloromethane. The organic layer was dried over anhydrous sodium sulfate, and inorganic substances were filtered off. The solvent was then distilled off under reduced pressure, and the residue was purified using a flash automatic purification apparatus (Isolera, manufactured by Biotage AB). ＴＭ The residue was purified by flash chromatography on silica gel using a HPLC system (eluted with ethyl acetate-hexane: 30%-60%) to give the title compound as a brown oil (800 mg, 94% yield).

[0521] Step 3: Preparation of N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-8-fluoro-5-methyl-3,4-dihydroisoquinolin-1(2H)-one The compound obtained in Step 2 of Example 5 above (1.04 g), 1,1,1-trifluoro-N-[2-(hydroxymethyl)phenyl]methanesulfonamide (1.07 g) (a compound described in WO 2010 / 026989 ), and paratoluenesulfonic acid monohydrate (90 mg) were dissolved in orthodichlorobenzene (5 mL), and the resulting solution was heated in a microwave synthesizer (Biotage AB / Initiator+). ＴＭ The reaction mixture was heated and stirred at 250°C for 8 minutes using a flash automatic purification device (Biotage AB / Isolera). ＴＭ The residue was purified by flash chromatography on silica gel using a HPLC system (eluted with ethyl acetate-hexane: 15%-60%) to give the title compound as a brown resinous solid (1.27 g, 64% yield).

[0522] Step 4: Preparation of N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-8-fluoro-5-methyl-3,4-dihydroisoquinolin-1(2H)-one The compound obtained in Step 3 of Example 5 above (724 mg), ethyl chloroformate (283 mg), and sodium bicarbonate (219 mg) were dissolved in acetonitrile (15 mL) and heated under reflux for 8 hours. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and the inorganic matter was filtered off. After the solvent was evaporated under reduced pressure, the residue was purified by a flash automatic purification system (Biotage AB / Isolera ＴＭ The residue was purified by silica gel flash chromatography on a 100% column (eluted with ethyl acetate-hexane: 10%-30%) to give the title compound as a pale yellow resinous solid (822 mg, 97% yield).

[0523] Example 6 Preparation of N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-8-fluoro-5-trifluoromethyl-3,4-dihydroisoquinolin-1(2H)-one (Compound 3-152)

[0524] Step 1: Preparation of 5-fluoro-2-trifluoromethylphenethylamine 5-Fluoro-2-trifluoromethylbenzeneacetonitrile (2.6 g) (a compound described in WO 2002 / 010143 ) and cobalt(II) chloride (2.49 g) were dissolved in methanol (65 mL), and sodium borohydride (3.63 g) was slowly added in an ice-water bath. The mixture was stirred overnight at room temperature. The reaction solution was filtered through Celite, and the solvent was evaporated under reduced pressure. After that, a 1 N aqueous solution of hydrochloric acid was added, and the mixture was washed with dichloromethane. Aqueous sodium hydroxide solution was added to the washed aqueous solution, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous sodium sulfate, and the inorganic matter was filtered off. The solvent was evaporated under reduced pressure to give the title compound as a brown oil (1.31 g, yield 49%).

[0525] Step 2: Preparation of methyl (5-fluoro-2-trifluoromethylphenethyl)carbamate The compound (1.31 g) obtained in Step 1 of Example 6 above and triethylamine (1.03 g) were dissolved in dichloromethane (30 mL), and methyl chloroformate (769 mg) was added dropwise in an ice-water bath, followed by stirring overnight at room temperature. Water was added to the reaction solution, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous sodium sulfate, and inorganic substances were filtered off. After the solvent was distilled off under reduced pressure, the residue was purified using a flash automatic purification system (Biotage AB / Isolera ＴＭ The residue was purified by flash chromatography on silica gel using a HPLC system (eluted with ethyl acetate-hexane: 5%-20%) to give the title compound as a yellow oil (1.17 g, 65% yield).

[0526] Step 3: Preparation of 8-fluoro-5-trifluoromethyl-3,4-dihydroisoquinolin-1(2H)-one The compound obtained in Step 2 of Example 6 (1.17 g) was dissolved in trifluoromethanesulfonic acid (5 mL), and the solution was heated at 47°C for 1 hour using a microwave synthesizer (Initiator+, manufactured by Biotage AB). ＴＭThe reaction mixture was heated and stirred at 160°C for 8 minutes using a centrifuge. The reaction mixture was added to ice water and extracted with dichloromethane. The organic layer was dried over anhydrous sodium sulfate, and inorganic substances were filtered off. The solvent was then distilled off under reduced pressure, and the residue was purified using a flash automatic purification apparatus (Isolera, manufactured by Biotage AB). ＴＭ The residue was purified by flash chromatography on silica gel using a HPLC system (eluted with ethyl acetate-hexane: 30%-60%) to give the title compound as a brown oil (918 mg, 89% yield).

[0527] Step 4: Preparation of N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-8-fluoro-5-trifluoromethyl-3,4-dihydroisoquinolin-1(2H)-one The compound obtained in Step 3 of Example 6 above (918 mg), 1,1,1-trifluoro-N-[2-(hydroxymethyl)phenyl]methanesulfonamide (887 mg) (a compound described in WO 2010 / 026989 ), and paratoluenesulfonic acid monohydrate (75 mg) were dissolved in orthodichlorobenzene (5 mL), and the resulting solution was heated in a microwave synthesizer (Biotage AB / Initiator+). ＴＭ The reaction mixture was heated and stirred at 250°C for 8 minutes using a flash automatic purification device (Biotage AB / Isolera). ＴＭ The residue was purified by flash chromatography on silica gel using a 100% hexanes column (eluted with ethyl acetate-hexane: 15%-50%) to give the title compound as a brown resinous solid (213 mg, 30% yield).

[0528] Step 5: Preparation of N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-8-fluoro-5-trifluoromethyl-3,4-dihydroisoquinolin-1(2H)-one The compound obtained in Step 4 of Example 6 above (336 mg), ethyl chloroformate (93 mg), and sodium bicarbonate (72 mg) were dissolved in acetonitrile (20 mL) and heated under reflux for 8 hours. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and the inorganic matter was filtered off. After the solvent was evaporated under reduced pressure, the residue was purified using a flash automatic purification system (Biotage AB / Isolera ＴＭ The residue was purified by silica gel flash chromatography on a 100% ethyl acetate / hexane system (eluted with ethyl acetate-hexane: 15%-50%) to give the title compound as a pale yellow resinous solid (367 mg, 95% yield).

[0529] Example 7 Preparation of N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-8-fluoro-5-methoxy-3,4-dihydroisoquinolin-1(2H)-one (Compound 3-153)

[0530] Step 1: Preparation of 5-fluoro-2-methoxyphenethylamine 5-Fluoro-2-methoxybenzeneacetonitrile (3.13 g) (a compound described in WO 2019 / 184955 ) and cobalt(II) chloride (3.69 g) were dissolved in methanol (95 mL), and sodium borohydride (5.38 g) was slowly added in an ice-water bath, followed by stirring at room temperature overnight. The reaction solution was filtered through Celite, and the solvent was evaporated under reduced pressure. After that, a 1 N aqueous solution of hydrochloric acid was added, and the mixture was washed with dichloromethane. Aqueous sodium hydroxide solution was added to the washed aqueous solution, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous sodium sulfate, and inorganic matter was filtered off. The solvent was evaporated under reduced pressure to give the title compound as a brown oil (1.82 g, yield 57%).

[0531] Step 2: Preparation of methyl (5-fluoro-2-methoxyphenethyl)carbamate The compound (1.82 g) obtained in Step 1 of Example 7 above and triethylamine (1.22 g) were dissolved in dichloromethane (40 mL), and methyl chloroformate (1.22 g) was added dropwise in an ice-water bath, followed by stirring overnight at room temperature. Water was added to the reaction solution, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous sodium sulfate, and inorganic substances were filtered off. After the solvent was distilled off under reduced pressure, the residue was purified using a flash automatic purification system (Biotage AB / Isolera ＴＭ The residue was purified by flash chromatography on silica gel using a HPLC system (eluted with ethyl acetate-hexane: 5%-20%) to give the title compound as a brown oil (1.65 g, 67% yield).

[0532] Step 3: Preparation of 8-fluoro-5-methoxy-3,4-dihydroisoquinolin-1(2H)-one The compound obtained in Step 2 of Example 7 (700 mg) was dissolved in trifluoromethanesulfonic acid (5 mL), and the solution was heated at 47°C for 1 hour using a microwave synthesizer (Initiator+, manufactured by Biotage AB). ＴＭ The reaction mixture was heated and stirred at 160°C for 8 minutes using a centrifuge. The reaction mixture was added to ice water and extracted with dichloromethane. The organic layer was dried over anhydrous sodium sulfate, and inorganic substances were filtered off. The solvent was then distilled off under reduced pressure, and the residue was purified using a flash automatic purification apparatus (Isolera, manufactured by Biotage AB). ＴＭ The residue was purified by flash chromatography on silica gel using a HPLC system (eluted with ethyl acetate-hexane: 30%-60%) to give the title compound as a brown oil (115 mg, 19% yield).

[0533] Step 4: Preparation of N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-8-fluoro-5-methoxy-3,4-dihydroisoquinolin-1(2H)-one The compound obtained in Step 3 of Example 7 above (115 mg), 1,1,1-trifluoro-N-[2-(hydroxymethyl)phenyl]methanesulfonamide (133 mg) (a compound described in WO 2010 / 026989 ), and paratoluenesulfonic acid monohydrate (11 mg) were dissolved in orthodichlorobenzene (5 mL), and the resulting solution was heated in a microwave synthesizer (Biotage AB / Initiator+). ＴＭ The reaction mixture was heated and stirred at 250°C for 8 minutes using a flash automatic purification device (Biotage AB / Isolera). ＴＭ The residue was purified by flash chromatography on silica gel using a HPLC system (eluted with ethyl acetate-hexane: 15%-50%) to give the title compound as a pale yellow resinous solid (155 mg, 61% yield).

[0534] Step 5: Preparation of N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-8-fluoro-5-methoxy-3,4-dihydroisoquinolin-1(2H)-one The compound obtained in Step 4 of Example 7 above (110 mg), ethyl chloroformate (83 mg), and sodium bicarbonate (63 mg) were dissolved in acetonitrile (10 mL) and heated under reflux for 8 hours. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and the inorganic matter was filtered off. After the solvent was evaporated under reduced pressure, the residue was purified using a flash automatic purification system (Biotage AB / Isolera ＴＭ The residue was purified by flash chromatography on silica gel using a column chromatography column (eluted with ethyl acetate-hexane: 5%-35%) to give the title compound as a colorless resinous solid (72 mg, 57% yield).

[0535] Example 8 Preparation of N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-8-chloro-5-fluoro-3,4-dihydroisoquinolin-1(2H)-one (Compound 3-154)

[0536] Step 1: Preparation of 8-chloro-5-fluoro-3,4-dihydroisoquinolin-1(2H)-one 5-Chloro-2-fluorophenethylamine (1.2 g) (a compound described in WO 2005 / 090287) and triethylamine (1.05 g) were dissolved in dichloromethane (20 mL), and methyl chloroformate (784 mg) was added dropwise in an ice-water bath, followed by stirring at room temperature overnight. Water was added to the reaction solution, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous sodium sulfate, and inorganic matter was filtered off, after which the solvent was distilled off under reduced pressure. The residue was dissolved in trifluoromethanesulfonic acid (5 mL) and the resulting mixture was subjected to a microwave synthesis using a microwave synthesis apparatus (Biotage AB / Initiator+). ＴＭ The reaction mixture was heated and stirred at 160°C for 5 minutes using a centrifuge. The reaction mixture was added to ice water and extracted with dichloromethane. The organic layer was dried over anhydrous sodium sulfate, and inorganic substances were filtered off. The solvent was then distilled off under reduced pressure, and the residue was purified using a flash automatic purification apparatus (Isolera, manufactured by Biotage AB). ＴＭ The residue was purified by flash chromatography on silica gel using a HPLC system (eluted with ethyl acetate-hexane: 30%-60%) to give the title compound as a brown oil (413 mg, 30% yield).

[0537] Step 2: Preparation of N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-8-chloro-5-fluoro-3,4-dihydroisoquinolin-1(2H)-one The compound obtained in Step 1 of Example 8 above (413 mg), 1,1,1-trifluoro-N-[2-(hydroxymethyl)phenyl]methanesulfonamide (466 mg) (a compound described in WO 2010 / 026989 ), and paratoluenesulfonic acid monohydrate (39 mg) were dissolved in orthodichlorobenzene (5 mL), and the resulting solution was heated in a microwave synthesizer (Biotage AB / Initiator+). ＴＭ The reaction mixture was heated and stirred at 250°C for 8 minutes using a flash automatic purification device (Biotage AB / Isolera). ＴＭThe residue was purified by flash chromatography on silica gel using a 100% hexanes column (eluted with ethyl acetate-hexane: 15%-50%) to give the title compound as a yellow oil (124 mg, 14% yield).

[0538] Step 3: Preparation of N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-8-chloro-5-fluoro-3,4-dihydroisoquinolin-1(2H)-one The compound obtained in Step 2 of Example 8 above (83 mg), ethyl chloroformate (41 mg), and sodium bicarbonate (32 mg) were dissolved in acetonitrile (10 mL) and heated under reflux for 8 hours. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and the inorganic matter was filtered off. After the solvent was evaporated under reduced pressure, the residue was purified using a flash automatic purification system (Biotage AB / Isolera ＴＭ The residue was purified by flash chromatography on silica gel using a HPLC system (eluted with ethyl acetate-hexane: 5%-35%) to give the title compound as a yellow oil (30 mg, 31% yield).

[0539] Example 9 Preparation of N-[2-[N-(2,2-difluoroethyl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one (Compound 3-178)

[0540] Step 1: Preparation of 2,2-difluoroethyloxycarbonyl chloride 2,2-Difluoroethanol (421 mg) and diisopropylethylamine (1.1 mL) were dissolved in dichloromethane (2.6 mL), and a solution of triphosgene (543 mg) in dichloromethane (2.6 mL) was added dropwise in an ice-water bath, followed by stirring at room temperature overnight. Water was added to the reaction solution, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous sodium sulfate, and inorganic substances were filtered off. The solvent was then evaporated under reduced pressure to give the title compound as a colorless liquid (503 mg, yield 68%).

[0541] Step 2: Preparation of N-[2-[N-(2,2-difluoroethyl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one The compound obtained in Step 6 of Example 4 above (132 mg) and sodium bicarbonate (265 mg) were dissolved in acetonitrile (3.2 mL), and the compound obtained in Step 1 of Example 9 above (503 mg) was added in an ice-water bath, followed by heating under reflux for 8 hours. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The resulting organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. After filtering off the inorganic matter, the solvent was evaporated under reduced pressure, and the residue was purified using a flash automatic purification system (Isolera, manufactured by Biotage AB). ＴＭ The residue was purified by flash chromatography on silica gel using a column chromatography column (eluted with ethyl acetate-hexane: 10%-30%) to give the title compound as a colorless resinous solid (75 mg, 45% yield).

[0542] Example 10 Preparation of N-[2-[N-(tetrahydrofuran-3-yl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one (Compound 3-200)

[0543] Step 1: Preparation of tetrahydrofuran-3-yl-oxycarbonyl chloride 3-Hydroxytetrahydrofuran (370 mg) and diisopropylethylamine (868 μL) were dissolved in dichloromethane (2.2 mL), and a solution of triphosgene (445 mg) in dichloromethane (2.0 mL) was added dropwise in an ice-water bath, followed by stirring at room temperature overnight. Water was added to the reaction solution, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous sodium sulfate, and inorganic substances were filtered off. The solvent was then evaporated under reduced pressure to give the title compound as a colorless liquid (620 mg, yield 98%).

[0544] Step 2: Preparation of N-[2-[N-(tetrahydrofuran-3-yl)oxycarbonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one The compound obtained in Step 5 of Example 4 above (309 mg) and diisopropylethylamine (812 μL) were dissolved in dichloromethane (7.8 mL), and a solution of the compound obtained in Step 1 of Example 10 above (620 mg) in dichloromethane (3 mL) was added dropwise in an ice-water bath, followed by stirring overnight at room temperature. A saturated aqueous solution of ammonium chloride was added to the reaction solution, and the mixture was extracted with dichloromethane. The extracted solution was washed with saturated saline and dried over sodium sulfate. After filtering off the inorganic matter, the solvent was distilled off under reduced pressure. The residue was purified using an automatic flash purification system (Biotage AB / Isolera ＴＭ The residue was purified by flash chromatography on silica gel using a column chromatography column (eluted with ethyl acetate-hexane: 30%-60%) to give the title compound as a colorless resinous solid (360 mg, 84% yield).

[0545] Step 3: Preparation of N-[2-[N-(tetrahydrofuran-3-yl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one The compound obtained in Step 2 of Example 10 above (543 mg) was dissolved in tetrahydrofuran (13.5 mL), and sodium hydride (108 mg, 60%) was added in an ice-water bath, followed by stirring at room temperature for 5 minutes. The mixture was again cooled in an ice-water bath, and trifluoromethanesulfonyl chloride (455 mg) was added dropwise, followed by stirring at room temperature overnight. A saturated aqueous solution of ammonium chloride was added to the reaction solution, followed by extraction with ethyl acetate. The extracted solution was washed with saturated brine, dried over sodium sulfate, and the inorganic matter was filtered off, and the solvent was then distilled off under reduced pressure. The residue was purified using an automatic flash purification system (Biotage AB / Isolera ＴＭ The residue was purified by silica gel flash chromatography on a 100% column (eluted with ethyl acetate-hexane: 30%-100%) to give the title compound as a colorless resinous solid (573 mg, 79% yield).

[0546] Example 11 Preparation of N-[2-(N-methanesulfonyl-N-trifluoromethanesulfonyl)aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one (Compound 3-247) The compound obtained in Step 6 of Example 4 above (800 mg) was dissolved in tetrahydrofuran (9.5 mL), and sodium hydride (380 mg, 60%) was added in an ice-water bath, followed by stirring at room temperature for 15 minutes. The mixture was again cooled in an ice-water bath, and methanesulfonyl chloride (1.09 g) was added dropwise, followed by heating under reflux for 8 hours. A saturated aqueous solution of ammonium chloride was added to the reaction mixture, which was then extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and the inorganic matter was filtered off. The solvent was then distilled off under reduced pressure, and the residue was purified using a flash automatic purification system (Biotage AB / Isolera ＴＭ The residue was purified by silica gel flash chromatography on a 100% ethyl acetate column (eluted with ethyl acetate-hexane: 5%-20%) to give the title compound as a colorless solid (630 mg, 67% yield).

[0547] Example 12 Preparation of N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)amino-5-fluoro-benzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one (Compound 4-30)

[0548] Step 1: Preparation of N-[2-(N-trifluoromethanesulfonyl)amino-5-fluorobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one The compound obtained in Step 3 of Example 4 above (340 mg), 1,1,1-trifluoro-N-[4-fluoro-2-(hydroxymethyl)phenyl]methanesulfonamide (507 mg) (a compound described in WO 2016 / 207081 ), and paratoluenesulfonic acid monohydrate (35 mg) were dissolved in orthodichlorobenzene (5 mL), and the resulting solution was heated in a microwave synthesizer (Biotage AB / Initiator+). ＴＭ The reaction mixture was heated and stirred at 250°C for 8 minutes using a flash automatic purification device (Biotage AB / Isolera). ＴＭThe residue was purified by flash chromatography on silica gel using a HPLC system (eluted with ethyl acetate-hexane: 15%-50%) to give the title compound as a colorless resinous solid (171 mg, 21% yield).

[0549] Step 2: Preparation of N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-5,6-dihydrothieno[2,3-c]pyridin-7(4H)-one The compound obtained in Step 1 of Example 12 above (79 mg), ethyl chloroformate (29 mg), and sodium bicarbonate (23 mg) were dissolved in acetonitrile (5 mL) and heated under reflux for 8 hours. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and the inorganic matter was filtered off. After the solvent was evaporated under reduced pressure, the residue was purified using a flash automatic purification system (Biotage AB / Isolera ＴＭ The residue was purified by flash chromatography on silica gel using a 5% to 20% ethyl acetate-hexane mixture (eluted with ethyl acetate-hexane: 5% to 20%) to give the title compound as a yellow oil (46 mg, 50% yield).

[0550] Example 13 Preparation of N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-9-chloro-2,3,4,5-tetrahydro-1H-2-benzazepin-1-one (Compound 5-2)

[0551] Step 1: Preparation of methyl [3-(2-chlorophenyl)propyl]carbamate 2-Chlorobenzenepropanamine (2.32 g) (a compound described in WO2017 / 177004) and triethylamine (3.51 mL) were dissolved in N,N-dimethylformamide (50 mL), and methyl chloroformate (1.94 mL) was added dropwise in an ice-water bath, followed by stirring overnight at room temperature. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and inorganic substances were filtered off. After the solvent was distilled off under reduced pressure, the residue was purified using a flash automatic purification system (Biotage AB / Isolera ＴＭ The residue was purified by flash chromatography on silica gel using a HPLC system (eluted with ethyl acetate-hexane: 7%-60%) to give the title compound as a colorless oil (2.28 g, 73% yield).

[0552] Step 2: Preparation of 9-chloro-2,3,4,5-tetrahydro-1H-2-benzazepin-1-one The compound obtained in Step 1 of Example 13 above (751 mg) was dissolved in trifluoromethanesulfonic acid (5 mL), and the solution was heated at 47°C for 1 hour using a microwave synthesizer (Initiator+, manufactured by Biotage AB). ＴＭ The mixture was heated and stirred at 160°C for 5 minutes using a 100% aqueous sodium hydroxide solution. The reaction mixture was added to ice water and extracted with dichloromethane. The organic layer was dried over anhydrous sodium sulfate to obtain a mixture of the title compound and 7-chloro-2,3,4,5-tetrahydro-1H-2-benzazepin-1-one as a colorless resinous solid (461 mg, yield 72%).

[0553] Step 3: Preparation of N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-9-chloro-2,3,4,5-tetrahydro-1H-2-benzazepin-1-one The mixture obtained in Step 2 of Example 13 (154 mg), 1,1,1-trifluoro-N-[2-(hydroxymethyl)phenyl]methanesulfonamide (177 mg) (a compound described in WO 2010 / 026989 ), and paratoluenesulfonic acid monohydrate (75 mg) were dissolved in orthodichlorobenzene (5 mL), and the resulting solution was heated in a microwave synthesizer (Biotage AB / Initiator+). ＴＭ The reaction mixture was heated and stirred at 250°C for 5 minutes using a flash automatic purification device (Biotage AB / Isolera). ＴＭ The residue was purified by silica gel flash chromatography on a microporous column (eluted with ethyl acetate-hexane: 15%-60%) to give the title compound as a yellow resinous solid (62 mg, 18% yield) and N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-chloro-2,3,4,5-tetrahydro-1H-2-benzazepin-1-one (Compound 5-5) as a yellow oil (158 mg, 46% yield).

[0554] Example 14 Preparation of N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-4,5-dihydro-6H-thieno[2,3-c]pyrrol-6-one (Compound 6-1)

[0555] Step 1: Preparation of methyl 3-bromomethyl-2-thiophenecarboxylate Methyl 3-methyl-2-thiophenecarboxylate (2.87 g) (a compound described in WO 2012 / 031004), N-bromosuccinimide (3.27 g), and benzoyl peroxide (297 mg, 75%) were dissolved in carbon tetrachloride (30 mL) and heated to reflux for 8 hours. After cooling, the reaction mixture was filtered through Celite. The solvent was evaporated under reduced pressure, and the residue was purified using a flash automatic purification system (Biotage AB / Isolera ＴＭ The residue was purified by flash chromatography on silica gel using a HPLC column (eluted with ethyl acetate-hexane: 5%-15%) to give the title compound as a yellow oil (1.87 g, 43% yield).

[0556] Step 2: Preparation of 4,5-dihydro-6H-thieno[2,3-c]pyrrol-6-one The compound obtained in Step 1 of Example 14 above (1.87 g) was dissolved in tetrahydrofuran (40 mL), and aqueous ammonia (20 mL) was added, followed by stirring at room temperature overnight. Water was added to the reaction solution, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous sodium sulfate, and the inorganic matter was filtered off, and the solvent was evaporated under reduced pressure. The residue was dissolved in a mixed solvent of methanol (20 mL) and ethanol (20 mL), and potassium carbonate (1.11 g) was added, followed by heating to reflux for 5 hours. Water was added to the reaction solution, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous sodium sulfate, and the inorganic matter was filtered off, and the solvent was evaporated under reduced pressure. The residue was purified by a flash automatic purification system (Isolera, manufactured by Biotage AB). ＴＭ The residue was purified by silica gel flash chromatography on a 1000 rpm PCT / EP2004 / 01004 HPLC system (eluted with chloroform-methanol: 3%-6%) to give the title compound as a pale yellow resinous solid (450 mg, 40% yield).

[0557] Step 3: Preparation of N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-4,5-dihydro-6H-thieno[2,3-c]pyrrol-6-one The compound obtained in Step 2 of Example 14 (65 mg), 1,1,1-trifluoro-N-[2-(hydroxymethyl)phenyl]methanesulfonamide (100 mg) (a compound described in WO 2010 / 026989 ), and paratoluenesulfonic acid monohydrate (42 mg) were dissolved in orthodichlorobenzene (5 mL), and the resulting solution was heated in a microwave synthesizer (Initiator+, manufactured by Biotage AB). ＴＭ The reaction mixture was heated and stirred at 250°C for 5 minutes using a flash automatic purification device (Biotage AB / Isolera). ＴＭ The residue was purified by flash chromatography on silica gel using a column chromatography column (eluted with ethyl acetate-hexane: 15%-60%) to give the title compound as a pale yellow resinous solid (140 mg, 84% yield).

[0558] Example 15 Preparation of N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5,6-dihydrofurano[2,3-c]pyrimidin-7(4H)-one (Compound 6-4)

[0559] Step 1: Preparation of methyl 2-[[[2-(furan-3-yl)ethyl]carbamoyl]oxy]benzoate The compound obtained in Step 1 of Example 4 above (2.02 g) and 3-furanethylamine (680 mg) (the compound described in US 2004 / 0087601) were dissolved in tetrahydrofuran (20 mL) and stirred overnight at room temperature. The reaction mixture was concentrated, and the residue was purified using a flash automatic purification system (Biotage AB / Isolera ＴＭ The residue was purified by flash chromatography on silica gel using a HPLC system (eluted with ethyl acetate-hexane: 5%-30...

Claims

1. (a) Formula [1] In the formula, A is an optionally substituted benzene ring or heteroaromatic ring, and E is -C(R ５ ) (R ６ ) -, oxygen atom, sulfur atom, SO, SO ２ , or N(R ７ ), W is an oxygen atom or a sulfur atom, o is 0 to 4, p is 0 to 4, m is 0 to 3, n is 0 to 3, and R １ HaloC １ ~C ６ is alkyl, R ２ is a hydrogen atom, Z １ C which may be substituted by one or more substituents selected from １ ~C ６ Alkyl, C ２ ~C ６ Alkenyl, HaloC ２ ~C ６ Alkenyl, C ２ ~C ６ Alkynyl, HaloC ２ ~C ６ Alkynyl, (C １ ~C １２ alkyl)carbonyl, (haloC １ ~C １２ alkyl)carbonyl, (C ３ ~C ６ cycloalkyl)carbonyl, (haloC ３ ~C ６ cycloalkyl)carbonyl, (C １ ~C ６ Alkyl C ３ ~C ６ cycloalkyl)carbonyl, C １ ~C ６ Alkyl (HaloC ３ ~C ６ cycloalkyl)carbonyl, (C ３ ~C ６ cycloalkoxy)carbonyl, (C ２ ~C ６ alkenyl)carbonyl, (haloC ２ ~C ６ alkenyl)carbonyl, Z ２ Phenyl (C ２ ~C ６ alkenyl)carbonyl, C １ ~C ６ Alkoxy (C ２ ~C ６ alkenyl)carbonyl, (C ２ ~C ６ alkynyl)carbonyl, Z ２ Phenylcarbonyl, which may be substituted by one or more substituents selected from ２ Heterocyclylcarbonyl optionally substituted by one or more substituents selected from ３ ~C ６ Cycloalkyl (C １ ~C ６ alkyl)carbonyl, Z ４ (C １ ~C ６ alkyl)carbonyl, (hydroxy C １ ~C ６ Alkyl)carbonyl, C １ ~C ６ Alkoxy (C １ ~C ６ Alkyl) carbonyl, haloC １ ~C ６ Alkoxy (C １ ~C ６ alkyl)carbonyl, Z ５ (C １ ~C ６ Alkyl) carbonyl, phenoxy (haloC １ ~C ６ alkyl)carbonyl, Z ５ Substituted by (HaloC １ ~C ６ alkyl)carbonyl, tri(C １ ~C ６ alkyl)silyloxy(C １ ~C ６ Alkyl)carbonyl, C １ ~C ６ Alkoxy C １ ~C ６ Alkoxy (C １ ~C ６ alkyl)carbonyl, (C １ ~C ６ Alkyl)carbonyl (C １ ~C ６ alkyl)carbonyl, (C １ ~C ６ Alkyl)carbonyloxy(C １ ~C ６ alkyl)carbonyl, (C １ ~C ６ Alkoxy)carbonyl (C １ ~C ６ Alkyl)carbonyl, C １ ~C ６ Alkylthio (C １ ~C ６ Alkyl) carbonyl, haloC １ ~C ６ Alkylthio (C １ ~C ６ alkyl)carbonyl, (C １ ~C １２ alkoxy)carbonyl, (haloC １ ~C ６ alkoxy)carbonyl, (C ３ ~C ６ cycloalkyloxy)carbonyl, (C ２ ~C ６ alkenyloxy)carbonyl, (haloC ２ ~C ６ alkenyloxy)carbonyl, (C ２ ~C ６ alkynyloxy)carbonyl, Z ２ phenoxycarbonyl, which may be substituted by one or more substituents selected from Z ２ Heterocyclyloxycarbonyl optionally substituted by one or more substituents selected from ３ ~C ６ Cycloalkyl (C １ ~C ６ alkoxy)carbonyl, Z ４ (C １ ~C ６ alkoxy)carbonyl, (cyano C １ ~C ６ alkoxy)carbonyl, (hydroxy C １ ~C ６ alkoxy)carbonyl, C １ ~C ６ Alkoxy (C １ ~C ６ alkoxy)carbonyl, C １ ~C ６ substituted with one or more substituents selected from alkoxy (C １ ~C ６ Alkoxy) carbonyl, haloC １ ~C ６ Alkoxy (C １ ~C ６ Alkoxy) carbonyl, tri C １ ~C ６ Alkylsilyloxy (C １ ~C ６ alkoxy)carbonyl, C １ ~C ６ Alkoxy C １ ~C ６ Alkoxy (C １ ~C ６ alkoxy)carbonyl, (C １ ~C ６ Alkyl)carbonyloxy(C １ ~C ６ alkoxy)carbonyl, C １ ~C ６ Alkyl sulfonyloxy (C １ ~C ６ alkoxy)carbonyl, (C １ ~C ６ Alkyl)carbonyl (C １ ~C ６ alkoxy)carbonyl, (C １ ~C ６ Alkoxy)carbonyl (C １ ~C ６ alkoxy)carbonyl, C １ ~C ６ Alkylthio (C １ ~C ６ Alkoxy) carbonyl, haloC １ ~C ６ Alkylthio (C １ ~C ６ alkoxy)carbonyl, C １ ~C ６ Alkyl sulfinyl (C １ ~C ６ alkoxy)carbonyl, C １ ~C ６ Alkyl sulfonyl (C １ ~C ６ alkoxy)carbonyl, (C １ ~C ６ alkylthio)carbonyl, (haloC １ ~C ６ alkylthio)carbonyl, mono(C １ ~C ６ alkyl)aminocarbonyl, mono(haloC １ ~C ６ alkyl)aminocarbonyl, di(C １ ~C ６ alkyl)aminocarbonyl, halodi(C １ ~C ６ alkyl)aminocarbonyl, C １ ~C ６ Alkoxyoxalyl, C １ ~C ６ Alkylsulfonyl, HaloC １ ~C ６ Alkylsulfonyl, C ３ ~C ６ Cycloalkylsulfonyl, C ２ ~C ６ Alkenylsulfonyl, HaloC １ ~C ６ Alkenylsulfonyl, Z ２ Phenylsulfonyl, optionally substituted by one or more substituents selected from Z ２ Heterocyclylsulfonyl, optionally substituted by one or more substituents selected from ３ ~C ６ Cycloalkyl C １ ~C ６ Alkylsulfonyl, Z ４ C substituted with one substituent selected from １ ~C ６ Alkylsulfonyl, C １ ~C ６ Alkoxy C １ ~C ６ Alkyl sulfonyl, amino sulfonyl, mono C １ ~C ６ alkylaminosulfonyl, di-C which may be the same or different １ ~C ６ Alkylaminosulfonyl, C １ ~C ６ Alkylthio, haloC １ ~C ６ alkylthio or cyano; Z １ are each independently a halogen atom, C ３ ~C ６ Cycloalkyl, Z ２ Phenyl which may be substituted by one or more substituents selected from ２ Heterocyclyl, cyano, Z ３ C which may be substituted by one or more substituents selected from １ ~C ６ Alkoxy, C ３ ~C ６ Cycloalkyloxy, Z ２ Phenoxy, which may be substituted by one or more substituents selected from Z ２ Phenylcarbonyloxy, which may be substituted by one or more substituents selected from Z ２ heterocyclylcarbonyloxy optionally substituted by one or more substituents selected from １ ~C ６ alkyl)carbonyloxy, (C ３ ~C ６ cycloalkyl)carbonyloxy, (C １ ~C ６ alkoxy)carbonyloxy, Z ２ phenoxycarbonyloxy, -CONR １１ R １２ C, which may be substituted by one or more halogen atoms １ ~C ６ alkylthio, C optionally substituted with one or more halogen atoms １ ~C ６ alkylsulfinyl, C optionally substituted by one or more halogen atoms １ ~C ６ Alkylsulfonyl, Z ２ phenylthio, which may be substituted by one or more substituents selected from ２ Phenylsulfinyl, which may be substituted by one or more substituents selected from ４ C optionally substituted with one substituent selected from １ ~C ６ Alkylthio, Z ４ C optionally substituted with one substituent selected from １ ~C ６ Alkylsulfinyl, Z ４ C optionally substituted with one substituent selected from １ ~C ６ alkylsulfinyl, thiocyanato, optionally substituted with one or more halogen atoms (C １ ~C ６ alkyl)carbonyl, optionally substituted with one or more halogen atoms (C １ ~C ６ alkoxy)carbonyl, and Z ２ phenylcarbonyl, optionally substituted by one or more substituents selected from ２ are each independently a halogen, C １ ~C ６ Alkyl, C ２ ~C ６ Alkenyl, C ２ ~C ６ Alkynyl, C ３ ~C ６ Cycloalkyl, haloC １ ~C ６ Alkyl, haloC ３ ~C ６ Cycloalkyl, C １ ~C ６ Alkoxy, HaloC １ ~C ６ Alkoxy, C １ ~C ６ Alkylthio, haloC １ ~C ６ Alkylthio, C １ ~C ６ Alkylsulfinyl, HaloC １ ~C ６ Alkylsulfinyl, C １ ~C ６ Alkylsulfonyl, HaloC １ ~C ６ Alkyl sulfonyl, phenyl, (C １ ~C ６ alkyl)carbonyl, (haloC １ ~C ６ alkyl)carbonyl, (C １ ~C ６ alkoxy)carbonyl, carboxyl, mono(C １ ~C ６ alkyl)aminocarbonyl, Z ６ phenyl substituted with one or more substituents selected from the following: ７ heterocyclyl optionally substituted by one or more substituents selected from the following: ７ phenoxy, which may be substituted by one or more substituents selected from the following: ７ phenylthio, which may be substituted by one or more substituents selected from the following: ７ phenylsulfinyl, which may be substituted by one or more substituents selected from the following: ７ phenylsulfonyl, which may be substituted by one or more substituents selected from the following: ７ Phenylcarbonyl, di(C １ ~C ６ alkyl)aminocarbonyl, -NR １３ R １４ , hydroxyl, cyano, or nitro; or two Z ２ may be combined with adjacent carbon or nitrogen atoms on the benzene ring or heterocycle to form a 5- or 6-membered carbocyclic or 5- or 6-membered heterocyclic ring, in which the heterocyclic ring is free of oxygen, sulfur, and nitrogen atoms (the nitrogen atoms being C １ ~C ６ Alkyl, C ２ ~C ６ Alkenyl, C ２ ~C ６ Alkynyl, or C ３ ~C ６ cycloalkyl), said carbocyclic or heterocyclic ring being optionally substituted by one or more halogens; the heteroaromatic ring is thiophene, furan, pyrrole, oxazole, isoxazoline, thiazole, isothiazole, pyrazole, imidazole, 1,3,4-oxadiazole, 1,2,4-oxadiazole, 1,3,4-thiadiazole, 1,2,4-thiadiazole, 1,2,4-triazole, 1,2,3-thiadiazole, 1,2,3-triazole, 1,2,3,4-tetrazole, pyridine, pyrimidine, pyrazine, pyridazine, 1,3,5-triazine, 1,2,4-triazine, benzothiophene, benzofuran, indole, benzothiazole, benzimidazole, benzisoxazole, benzisothiazole, indazole, benzoxazole, quinoline, isoquinoline, quinoxaline, phthalazine, cinnoline, or quinazoline; The heterocyclyl may be thienyl, furyl, pyrrolyl, oxazolyl, isoxazolyl, isoxazolinyl, thiazolyl, isothiazolyl, pyrazolyl, imidazolyl, 1,3,4-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,4-triazolyl, 1,2,3-thiadiazolyl, 1,2,3-triazolyl, 1,2,3,4-tetrazolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, 1,3,5-triazinyl, 1,2,4-triazinyl, benzothienyl, benzofuranyl, 1,3,4-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,4-triazolyl, 1,2,3-triazolyl, 1,2,3,4-tetrazolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, 1,3,5-triazinyl, 1,2,4-triazinyl, benzothienyl, benzofuranyl, 1,3,4-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,4-triazinyl, 1,3,5-triazinyl, benzothienyl, benzofuranyl, 1,3,4-oxadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-thiadiazolyl, Z is aryl, indolyl, benzothiazolyl, benzimidazolyl, benzisoxazolyl, benzisothiazolyl, indazolyl, benzoxazolyl, quinolyl, isoquinolyl, quinoxalinyl, phthalazinyl, cinnolinyl, quinazolinyl, oxiranyl, oxetanyl, tetrahydrofuranyl, tetrahydrothienyl, 1,1-dioxytetrahydrothienyl, tetrahydropyranyl, tetrahydrothiopyranyl, 1,3-dioxanyl, 2-oxo-1,3-dioxolanyl, 2-oxo-1,3-dioxolyl, or 2,5-dioxopyrrolidinyl; ３ is a halogen atom, Z ２ Phenyl, triC １ ~C ６ Alkylsilyl, C １ ~C ６ alkyldiphenylsilyl, C optionally substituted with one or more halogen atoms １ ~C ６ Alkoxy, Z ２ Phenylcarbonyloxy optionally substituted by one or more substituents selected from ２ Z is phenylsulfonyl, which may be substituted by one or more substituents selected from ４ Is, Z ２ Phenyl optionally substituted by one or more substituents selected from ２ Z is a heterocyclyl optionally substituted by one or more substituents selected from ５ Is, Z ２ phenoxy optionally substituted by one or more substituents selected from ６ Is Ji (C １ ~C ６ Z is selected from the group consisting of alkyl, aminocarbonyl, hydroxy, amino, cyano and nitro; ７ is halogen, C １ ~C ６ Alkyl, C ２ ~C ６ Alkenyl, C ２ ~C ６ Alkynyl, C ３ ~C ６ Cycloalkyl, haloC １ ~C ６ Alkyl, haloC ３ ~C ６ Cycloalkyl, C １ ~C ６ Alkoxy, HaloC １ ~C ６ Alkoxy, C １ ~C ６ Alkylthio, haloC １ ~C ６ Alkylthio, C １ ~C ６ Alkylsulfinyl, HaloC １ ~C ６ Alkylsulfinyl, C １ ~C ６ Alkylsulfonyl, HaloC １ ~C ６ Alkylsulfonyl, (C １ ~C ６ alkyl)carbonyl, (haloC １ ~C ６ alkyl)carbonyl, (C １ ~C ６ alkoxy)carbonyl, carboxyl, mono(C １ ~C ６ alkyl)aminocarbonyl, di(C １ ~C ６ Z is selected from the group consisting of alkyl, aminocarbonyl, hydroxyl, amino, cyano, and nitro; ８ Is, Z ２ phenylthio, which may be substituted by one or more substituents selected from ２ Phenylsulfinyl, which may be substituted by one or more substituents selected from ２ phenylsulfonyl, optionally substituted by one or more substituents selected from １１ and R １２ are each independently a hydrogen atom, C １ ~C ６ Alkyl, and Z ２ phenyl, optionally substituted with one or more substituents selected from １３ is a hydrogen atom or C １ ~C ６ alkyl; R １４ is a hydrogen atom, or Z ７ R is a phenyl group optionally substituted by one or more substituents selected from ３ and R ４ are each independently a hydrogen atom, C １ ~C ６ Alkyl, haloC １ ~C ６ Alkyl, C １ ~C ６ Cycloalkyl, haloC １ ~C ６ Cycloalkyl, C １ ~C ６ Alkoxy, HaloC １ ~C ６ alkoxy, halogen, or cyano; or R ３ and R ４ can be bonded to each other to form a 3- to 7-membered ring, R ５ and R ６ are each independently a hydrogen atom, a halogen atom, or C １ ~C ６ Alkyl, haloC １ ~C ６ Alkyl, C ２ ~C ６ Alkenyl, C ２ ~C ６ Alkynyl, C ３ ~C ６ Cycloalkyl, haloC ３ ~C ６ Cycloalkyl, Hydroxy C １ ~C ６ Alkyl, C １ ~C ６ Alkoxy C １ ~C ６ Alkyl, haloC １ ~C ６ Alkoxy C １ ~C ６ Alkyl, C １ ~C ６ Alkylthio C １ ~C ６ Alkyl, haloC １ ~C ６ Alkylthio C １ ~C ６ Alkyl, mono(C １ ~C ６ Alkyl)amino C １ ~C ６ alkyl, di(C １ ~C ６ Alkyl)amino C １ ~C ６ Alkyl, Z ２ Phenyl which may be substituted by one or more substituents selected from ２ Heterocyclyl optionally substituted by one or more substituents selected from ４ C substituted with one substituent selected from １ ~C ６ Alkyl, Z ５ C substituted with one substituent selected from １ ~C ６ Alkyl, (C １ ~C ６ alkyl)carbonyl, (haloC １ ~C ６ alkyl)carbonyl, Z ２ Phenylcarbonyl, which may be substituted by one or more substituents selected from (C １ ~C ６ alkoxy)carbonyl, (haloC １ ~C ６ alkoxy)carbonyl, carboxyl, -NR １１ R １２ , C １ ~C ６ Alkoxy, HaloC １ ~C ６ Alkoxy, Z ２ Phenoxy, optionally substituted by one or more substituents selected from １ ~C ６ Alkylthio, haloC １ ~C ６ Alkylthio, Z ２ Phenylthio, optionally substituted by one or more substituents selected from １ ~C ６ Alkylsulfonyl, HaloC １ ~C ６ Alkylsulfonyl, mono(C １ ~C ６ alkyl)amino, di(C １ ~C ６ alkyl)amino, (C １ ~C ６ alkyl)carbonyloxy, hydroxyl, amino, cyano, or nitro, or R ５ and R ６ are bonded to each other to form an oxygen atom, a sulfur atom, and a nitrogen atom (the nitrogen atom is C １ ~C ６ Alkyl, C ２ ~C ６ Alkenyl, C ２ ~C ６ Alkynyl, or C ３ ~C ６ or R ５ and R ６ R on different carbons ５ Or R ６ and an oxygen atom, a sulfur atom, and a nitrogen atom (the nitrogen atom is C １ ~C ６ Alkyl, C ２ ~C ６ Alkenyl, C ２ ~C ６ Alkynyl, or C ３ ~C ６ C, which may be interrupted by 1 or 2 heteroatoms selected from the group consisting of cycloalkyl, １ ~C ４ Alkylene, HaloC １ ~C ４ Alkylene, C ２ ~C ４ Alkenylene or haloC ２ ~C ４ Alkenylene can form a 3- to 8-membered ring, or R ５ and R ６ is R on adjacent carbons ５ Or R ６ can form a bond together with R ７ is a hydrogen atom, C １ ~C ６ Alkyl, haloC １ ~C ６ Alkyl, C ３ ~C ６ Cycloalkyl, haloC ３ ~C ６ Cycloalkyl, C ２ ~C ６ Alkenyl, HaloC ２ ~C ６ Alkenyl, C ２ ~C ６ Alkynyl, Hydroxy C １ ~C ６ Alkyl, C １ ~C ６ Alkoxy C １ ~C ６ Alkyl, haloC １ ~C ６ Alkoxy C １ ~C ６ Alkyl, C ３ ~C ６ Cycloalkyl C １ ~C ６ Alkyl, Z ４ C substituted with one substituent selected from １ ~C ６ Alkyl, Z ２ Phenyl which may be substituted by one or more substituents selected from ４ C substituted with one substituent selected from １ ~C ６ Alkyl, (C １ ~C ６ Alkyl)carbonyl C １ ~C ６ Alkyl, (haloC １ ~C ６ Alkyl)carbonyl C １ ~C ６ Alkyl, (C １ ~C ６ Alkoxy)carbonyl C １ ~C ６ Alkyl, (haloC １ ~C ６ Alkoxy)carbonyl C １ ~C ６ Alkyl, (C １ ~C ６ alkyl)carbonyl, (haloC １ ~C ６ alkyl)carbonyl, (C ３ ~C ６ cycloalkyl)carbonyl, C ３ ~C ６ Cycloalkyl (C １ ~C ６ alkyl)carbonyl, (C ２ ~C ６ alkenyl)carbonyl, Z ２ Phenylcarbonyl, which may be substituted by one or more substituents selected from ２ Heterocyclylcarbonyl optionally substituted by one or more substituents selected from (C １ ~C ６ alkoxy)carbonyl, (haloC １ ~C ６ alkoxy)carbonyl, Z ２ Phenoxycarbonyl, aminocarbonyl, mono(C １ ~C ６ alkyl)aminocarbonyl, monohalo(C １ ~C ６ alkyl)aminocarbonyl, di(C １ ~C ６ alkyl)aminocarbonyl, halodi(C １ ~C ６ alkyl)aminocarbonyl, (C １ ~C ６ alkylthio)carbonyl, (haloC １ ~C ６ (alkylthio)carbonyl, C １ ~C ６ Alkylsulfonyl, HaloC １ ~C ６ Alkylsulfonyl, Z ２ Phenylsulfonyl, optionally substituted by one or more substituents selected from １ ~C ６ Alkylthio C １ ~C ６ Alkyl, haloC １ ~C ６ Alkylthio C １ ~C ６ Alkyl, Z ８ C substituted with one substituent selected from １ ~C ６ Alkyl, C １ ~C ６ Alkylsulfinyl C １ ~C ６ Alkyl, haloC １ ~C ６ Alkylsulfinyl C １ ~C ６ Alkyl, C １ ~C ６ Alkylsulfonyl C １ ~C ６ Alkyl, haloC １ ~C ６ Alkylsulfonyl C １ ~C ６ alkyl, cyano, amino, or hydroxy; X is independently a hydrogen atom, a halogen atom, １ ~C ６ Alkyl, C ２ ~C ６ Alkenyl, C ２ ~C ６ Alkynyl, C ３ ~C ６ Cycloalkyl, haloC １ ~C ６ Alkyl, haloC ２ ~C ６ Alkenyl, HaloC ２ ~C ６ Alkynyl, HaloC ３ ~C ６ Cycloalkyl, C １ ~C ６ Alkoxy, HaloC １ ~C ６ Alkoxy, C ２ ~C ６ Alkenyloxy, C ２ ~C ６ Alkynyloxy, C ３ ~C ６ Cycloalkyl C １ ~C ６ Alkyloxy, Phenyl C １ ~C ６ Alkyloxy, (C １ ~C ６ alkyl)carbonyloxy, Z ２ Phenylcarbonyloxy, which may be substituted by one or more substituents selected from Z ２ Heterocyclylcarbonyloxy, optionally substituted by one or more substituents selected from (C １ ~C ６ alkoxy)carbonyloxy, (C １ ~C ６ alkylthio)carbonyloxy, C １ ~C ６ Alkyl sulfonyloxy, halo C １ ~C ６ Alkyl sulfonyloxy, phenyl sulfonyloxy, diC １ ~C ６ Alkylphosphorooxy, TriC １ ~C ６ Alkylsilyloxy, C １ ~C ６ Alkoxy C １ ~C ６ Alkyl, C １ ~C ６ Alkylthio, haloC １ ~C ６ Alkylthio, C １ ~C ６ Alkylsulfinyl, HaloC １ ~C ６ Alkylsulfinyl, C １ ~C ６ Alkylsulfonyl, HaloC １ ~C ６ Alkylsulfonyl, Z ２ Phenyl which may be substituted by one or more substituents selected from ２ Heterocyclyl optionally substituted by one or more substituents selected from ２ Phenoxy, which may be substituted by one or more substituents selected from Z ２ phenylthio, which may be substituted by one or more substituents selected from ２ Phenylsulfinyl, which may be substituted by one or more substituents selected from ２ Phenylsulfonyl, di(C １ ~C ６ alkyl)amino, (C １ ~C ６ alkyl)carbonylamino, bis((C １ ~C ６ Alkyl)carbonyl)amino, haloC １ ~C ６ Alkylsulfonylamino, morpholinyl, isoindoline-1,3-dione-2-yl, (C １ ~C ６ alkyl)carbonyl, (haloC １ ~C ６ alkyl)carbonyl, Z ２ Phenylcarbonyl, which may be substituted by one or more substituents selected from (C １ ~C ６ alkoxy)carbonyl, carboxyl, mono(C １ ~C ６ alkyl)aminocarbonyl, di(C １ ~C ６ alkyl)aminocarbonyl, Z ２ phenylaminocarbonyl, phenyl (C １ ~C ６ alkylamino)carbonyl, Z ４ (C １ ~C ６ or two X's attached to adjacent carbon or nitrogen atoms on a benzene ring or heterocycle together with the ring atoms to which they are attached form a 4- to 6-membered carbocyclic or heterocyclic ring, the heterocyclic ring containing one or two heteroatoms selected from the group consisting of oxygen, sulfur, and nitrogen atoms, the nitrogen atom being C １ ~C ６ Alkyl, C ２ ~C ６ Alkenyl, C ２ ~C ６ Alkynyl, or C ３ ~C ６ Each Y is independently a hydrogen atom, a halogen atom, a C １ ~C ６ Alkyl, C ２ ~C ６ Alkenyl, C ２ ~C ６ Alkynyl, C ３ ~C ６ Cycloalkyl, haloC １ ~C ６ Alkyl, haloC ２ ~C ６ Alkenyl, HaloC ２ ~C ６ Alkynyl, HaloC ３ ~C ６ Cycloalkyl, C １ ~C ６ Alkoxy, HaloC １ ~C ６ Alkoxy, C ２ ~C ６ Alkenyloxy, C ２ ~C ６ Alkynyloxy, C ３ ~C ６ Cycloalkyl C １ ~C ６ Alkyloxy, Phenyl C １ ~C ６ Alkyloxy, (C １ ~C ６ alkyl)carbonyloxy, Z ２ Phenylcarbonyloxy, which may be substituted by one or more substituents selected from Z ２ Heterocyclylcarbonyloxy, optionally substituted by one or more substituents selected from (C １ ~C ６ alkoxy)carbonyloxy, (C １ ~C ６ alkylthio)carbonyloxy, C １ ~C ６ Alkyl sulfonyloxy, halo C １ ~C ６ Alkyl sulfonyloxy, phenyl sulfonyloxy, diC １ ~C ６ Alkylphosphorooxy, TriC １ ~C ６ Alkylsilyloxy, C １ ~C ６ Alkoxy C １ ~C ６ Alkyl, C １ ~C ６ Alkylthio, haloC １ ~C ６ Alkylthio, C １ ~C ６ Alkylsulfinyl, HaloC １ ~C ６ Alkylsulfinyl, C １ ~C ６ Alkylsulfonyl, HaloC １ ~C ６ Alkylsulfonyl, Z ２ Phenyl which may be substituted by one or more substituents selected from ２ Heterocyclyl optionally substituted by one or more substituents selected from ２ Phenoxy, which may be substituted by one or more substituents selected from Z ２ phenylthio, which may be substituted by one or more substituents selected from ２ Phenylsulfinyl, which may be substituted by one or more substituents selected from ２ Phenylsulfonyl, di(C １ ~C ６ alkyl)amino, (C １ ~C ６ alkyl)carbonylamino, bis((C １ ~C ６ Alkyl)carbonyl)amino, haloC １ ~C ６ Alkylsulfonylamino, morpholinyl, isoindoline-1,3-dione-2-yl, (C １ ~C ６ alkyl)carbonyl, (haloC １ ~C ６ alkyl)carbonyl, Z ２ Phenylcarbonyl, which may be substituted by one or more substituents selected from (C １ ~C ６ alkoxy)carbonyl, carboxyl, -NR １１ R １２ , hydroxy, amino, cyano, or nitro; or two Y's together with adjacent carbon or nitrogen atoms on the benzene ring may form a 5- or 6-membered carbocyclic or 5- or 6-membered heterocyclic ring, in which the heterocyclic ring is free of oxygen, sulfur, and nitrogen atoms (the nitrogen atoms being C １ ~C ６ Alkyl, C ２ ~C ６ Alkenyl, C ２ ~C ６ Alkynyl, or C ３ ~C ６ and (b) at least one agricultural and horticultural herbicide.

2. (a') Formula [1a] {wherein E is -CH ２ -, W is an oxygen atom or a sulfur atom, m is 0, n is 0, 1 or 3, R １ Fluoro C １ ~C ６ is alkyl, R ２ is a hydrogen atom, C １ ~C ６ Alkoxy C １ ~C ６ Alkyl, or (C １ ~C １２ alkoxy)carbonyl, R ３ and R ４ is a hydrogen atom, and X １ , X ２ , X ３ and X ４ are each independently a hydrogen atom, a halogen, or C １ ~C ６ Alkyl, haloC １ ~C ６ Alkyl, C １ ~C ６ Alkoxy, C ２ ~C ６ Alkenyloxy, C ２ ~C ６ Alkynyloxy, C ３ ~C ６ Cycloalkyl C １ ~C ６ Alkyloxy, Phenyl C １ ~C ６ Alkyloxy, (C １ ~C ６ alkyl)carbonyloxy, Z ２ Phenylcarbonyloxy, heterocyclylcarbonyloxy, (C １ ~C ６ alkoxy)carbonyloxy, (C １ ~C ６ alkylthio)carbonyloxy, C １ ~C ６ Alkyl sulfonyloxy, halo C １ ~C ６ Alkyl sulfonyloxy, phenyl sulfonyloxy, diC １ ~C ６ Alkylphosphorooxy, TriC １ ~C ６ Alkylsilyloxy, C １ ~C ６ Alkoxy C １ ~C ６ alkyl, phenyl, hydroxyl, amino, cyano, or nitro; Y １ , Y ２ , Y ３ and Y ４ are each independently a hydrogen atom or a haloC １ ~C ６ is alkyl, ２ The herbicidal composition according to claim 1, which comprises a compound represented by the following formula: embedded image wherein R is nitro; or a salt thereof; and (b) at least one agricultural and horticultural herbicide.

3. (a'') Formula [1a] {wherein E is -CH ２ -, W is an oxygen atom or a sulfur atom, m is 0, n is 2, and R １ Fluoro C １ ~C ６ is alkyl, R ２ is a hydrogen atom, C ２ ~C ６ Alkynyl, Z ４ C substituted with one substituent selected from １ ~C ６ Alkyl, Cyano C １ ~C ６ Alkyl, C １ ~C ６ Alkoxy C １ ~C ６ Alkyl, (C １ ~C ６ Alkoxy)carbonyloxy C １ ~C ６ Alkyl, (C １ ~C １２ alkyl)carbonyl, (haloC １ ~C １２ alkyl)carbonyl, (C ３ ~C ６ cycloalkyl)carbonyl, C １ ~C ６ Alkyl (C ３ ~C ６ cycloalkyl)carbonyl, C １ ~C ６ Alkyl halo (C ３ ~C ６ cycloalkyl)carbonyl, (C ２ ~C ６ alkenyl)carbonyl, C １ ~C ６ Alkoxy (C ２ ~C ６ alkenyl)carbonyl, phenylcarbonyl, Z ２ Heterocyclylcarbonyl optionally substituted by one or more substituents selected from ３ ~C ６ Cycloalkyl (C １ ~C ６ alkyl) carbonyl, hydroxy (C １ ~C ６ Alkyl)carbonyl, C １ ~C ６ Alkoxy (C １ ~C ６ alkyl)carbonyl, tri(C １ ~C ６ alkyl)silyloxy(C １ ~C ６ alkyl)carbonyl, (C １ ~C ６ Alkyl)carbonyloxy(C １ ~C ６ Alkyl)carbonyl, C １ ~C ６ Alkylthio (C １ ~C ６ alkyl)carbonyl, (C １ ~C １２ alkoxy)carbonyl, (haloC １ ~C ６ alkoxy)carbonyl, (C ３ ~C ６ cycloalkyloxy)carbonyl, (C ２ ~C ６ alkenyloxy)carbonyl, (C ２ ~C ６ alkynyloxy)carbonyl, Z ２ phenoxycarbonyl, which may be substituted by one or more substituents selected from Z ２ Heterocyclyloxycarbonyl optionally substituted by one or more substituents selected from ３ ~C ６ Cycloalkyl (C １ ~C ６ alkoxy)carbonyl, Z ４ (C １ ~C ６ alkoxy)carbonyl, (cyano C １ ~C ６ alkoxy)carbonyl, (hydroxy C １ ~C ６ alkoxy)carbonyl, C １ ~C ６ Alkoxy (C １ ~C ６ alkoxy)carbonyl, C １ ~C ６ substituted with one or more substituents selected from alkoxy (C １ ~C ６ alkoxy)carbonyl, (C １ ~C ６ alkyl)diphenylsilyloxy(C １ ~C ６ alkoxy)carbonyl, (C １ ~C ６ Alkyl)carbonyloxy(C １ ~C ６ alkoxy)carbonyl, C １ ~C ６ Alkyl sulfonyloxy (C １ ~C ６ alkoxy)carbonyl, (C １ ~C ６ Alkyl)carbonyl (C １ ~C ６ alkoxy)carbonyl, (C １ ~C ６ Alkoxy)carbonyl (C １ ~C ６ alkoxy)carbonyl, C １ ~C ６ Alkylthio (C １ ~C ６ alkoxy)carbonyl, C １ ~C ６ Alkyl sulfonyl (C １ ~C ６ alkoxy)carbonyl, (C １ ~C ６ alkylthio)carbonyl, mono(C １ ~C ６ alkyl)aminocarbonyl, di(C １ ~C ６ alkyl)aminocarbonyl, C １ ~C ６ Alkylsulfonyl, HaloC １ ~C ６ Alkylsulfonyl, or C ３ ~C ６ cycloalkylsulfonyl, R ３ and R ４ is a hydrogen atom, and X １ , X ２ , X ３ and X ４ are each independently a hydrogen atom, a halogen, or C １ ~C ６ Alkyl, C ３ ~C ６ Cycloalkyl, haloC １ ~C ６ Alkyl, C １ ~C ６ Alkoxy, HaloC １ ~C ６ Alkoxy, C ２ ~C ６ Alkynyloxy, (C １ ~C ６ alkyl)carbonyloxy, phenylcarbonyloxy, (C １ ~C ６ alkoxy)carbonyloxy, C １ ~C ６ Alkyl sulfonyloxy, halo C １ ~C ６ Alkylsulfonyloxy, C １ ~C ６ Alkylthio, C １ ~C ６ alkylsulfonyl, phenyl, di(C １ ~C ６ alkyl)amino, (C １ ~C ６ alkyl)carbonylamino, bis((C １ ~C ６ Alkyl)carbonyl)amino, haloC １ ~C ６ Alkylsulfonylamino, morpholinyl, isoindoline-1,3-dione-2-yl, (C １ ~C ６ alkoxy)carbonyl, hydroxyl, cyano, or nitro; or X １ and X ２ , X ２ and X ３ , and X ３ and X ４ may together with the carbon atom to which they are attached form a 5- or 6-membered carbocyclic ring or a 5- or 6-membered heterocyclic ring, wherein the heterocyclic ring contains 1 or 2 heteroatoms selected from sulfur and nitrogen atoms; Y １ , Y ２ , Y ３ and Y ４ are each independently a hydrogen atom, a halogen, or C １ ~C ６ Alkyl, haloC １ ~C ６ Alkyl, C １ ~C ６ alkoxy or hydroxyl group, or Y １ and Y ２ , Y ２ and Y ３ , and Y ３ and Y ４ may form a 4- to 6-membered carbocyclic ring together with the carbon atom to which they are attached, ２ is C １ ~C ６ Alkyl, C １ ~C ６ alkoxy, or nitro, and the heterocyclyl is thienyl, furyl, pyrrolyl, oxiranyl, oxetanyl, tetrahydrofuranyl, tetrahydrothienyl, 1,1-dioxytetrahydrothienyl, tetrahydropyranyl, tetrahydrothiopyranyl, 1,3-dioxanyl, 2-oxo-1,3-dioxolyl, 2-oxo-1,3-dioxolyl, or 2,5-dioxopyrrolidinyl); or a salt thereof; and (b) at least one agricultural and horticultural herbicide.

4. In the formula [1a], n is 2, R １ is trifluoromethyl; R ２ is a hydrogen atom, (C ３ ~C ６ cycloalkyl)carbonyl, (C ２ ~C ４ alkenyl)carbonyl, C １ ~C ６ Alkoxy (C １ ~C ６ alkyl)carbonyl, 2-furylcarbonyl, C １ ~C ６ Alkylthio (C １ ~C ６ alkyl)carbonyl, (C １ ~C ５ alkoxy)carbonyl, (haloC １ ~C ３ alkoxy)carbonyl, (C ３ ~C ４ cycloalkyloxy)carbonyl, (C ２ ~C ３ alkynyloxy)carbonyl, heterocyclyloxycarbonyl, C ３ ~C ４ Cycloalkyl (C １ ~C ２ alkoxy) carbonyl, heterocyclyl (C １ ~C ２ alkoxy)carbonyl, (cyano C １ ~C ６ alkoxy)carbonyl, (hydroxy C １ ~C ６ alkoxy)carbonyl, C １ ~C ６ Alkoxy (C １ ~C ６ alkoxy)carbonyl, C １ ~C ２ Alkylsulfonyl, or (C １ ~C ４ alkylthio)carbonyl, １ is a fluorine atom, a chlorine atom, or a methyl atom; X ２ and X ３ is a hydrogen atom, and X ４ is a hydrogen atom, a fluorine atom, a chlorine atom, methyl, trifluoromethyl, or methoxy; １ , Y ２ , Y ３ and Y ４ The herbicidal composition of claim 3, wherein: is a hydrogen atom; and said heterocyclyl is oxiranyl, oxetanyl, tetrahydrofuranyl, or tetrahydropyranyl.

5. Formula [1b] where Het is E is selected from -CH ２ -, W is an oxygen atom, m is 0, n is 1 to 2, and R １ Fluoro C １ ~C ６ is alkyl, R ２ is a hydrogen atom or (C １ ~C １２ alkoxy)carbonyl, R ３ and R ４ is a hydrogen atom, and Y １ , Y ２ , Y ３ and Y ４ 2. The herbicidal composition according to claim 1, comprising a compound represented by the formula (I): wherein R is a hydrogen atom, or a salt thereof; and (b) at least one agricultural and horticultural herbicide.

6. In the formula [1b], Het is Het-1 or Het-2, n is 2, and R １ is trifluoromethyl; R ２ is a hydrogen atom or (C ２ ~C ６ 6. The herbicidal composition of claim 5, wherein said herbicidal composition is a aryloxycarbonyl.

7. The compound represented by the formula [1] or a salt thereof is N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-azabicyclo[4.2.0]octa-1(6),2,4-trien-8-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5-fluoro-7-azabicyclo[4.2.0]octa-1(6),2,4-trien-8-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-4-fluoro-7-azabicyclo[4.2.0]octa-1(6),2,4-trien-8-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-3-fluoro-7-azabicyclo[4.2.0]octa-1(6),2,4-trien-8-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-2-fluoro-7-azabicyclo[4.2.0]octa-1(6),2,4-trien-8-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-2-trifluoromethyl-7-azabicyclo[4.2.0]octa-1(6),2,4-trien-8-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-2,5-dichloro-7-azabicyclo[4.2.0]octa-1(6),2,4-trien-8-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-3,4-difluoro-7-azabicyclo[4.2.0]octa-1(6),2,4-trien-8-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-5-fluoro-7-azabicyclo[4.2.0]octa-1(6),2,4-trien-8-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-4-fluoro-7-azabicyclo[4.2.0]octa-1(6),2,4-trien-8-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-3-fluoro-7-azabicyclo[4.2.0]octa-1(6),2,4-trien-8-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-1,3-dihydroisoindol-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-fluoro-1,3-dihydroisoindol-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-chloro-1,3-dihydroisoindol-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-bromo-1,3-dihydroisoindol-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-methyl-1,3-dihydroisoindol-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-phenyl-1,3-dihydroisoindol-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-cyano-1,3-dihydroisoindol-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-hydroxy-1,3-dihydroisoindol-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-methoxy-1,3-dihydroisoindol-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-acetoxy-1,3-dihydroisoindol-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-benzoyloxy-1,3-dihydroisoindol-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-(4-nitrobenzoyl)oxy-1,3-dihydroisoindol-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-methoxycarbonyloxy-1,3-dihydroisoindol-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-(2-propylthio)carbonyloxy-1,3-dihydroisoindol-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-(1H-imidazol-1-yl-carbonyloxy)-1,3-dihydroisoindol-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-(pyrrolidin-1-yl-carbonyloxy)-1,3-dihydroisoindol-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-methanesulfonyloxy-1,3-dihydroisoindol-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-trifluoromethanesulfonyloxy-1,3-dihydroisoindol-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-phenylsulfonyloxy-1,3-dihydroisoindol-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-diethylphosphorooxy-1,3-dihydroisoindol-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-tertiary butyldimethylsilyloxy-1,3-dihydroisoindol-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-propargyloxy-1,3-dihydroisoindol-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-allyloxy-1,3-dihydroisoindol-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-benzyloxy-1,3-dihydroisoindol-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-cyclopropylmethyloxy-1,3-dihydroisoindol-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-amino-1,3-dihydroisoindol-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-acetylamino-1,3-dihydroisoindol-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-bisacetylamino-1,3-dihydroisoindol-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-trifluoromethanesulfonylamino-1,3-dihydroisoindol-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-(isoindoline-1,3-dione-2-yl)-1,3-dihydroisoindol-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-6-fluoro-1,3-dihydroisoindol-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-6-methyl-1,3-dihydroisoindol-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-6-hydroxy-1,3-dihydroisoindol-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-6-methoxy-1,3-dihydroisoindol-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-6-acetoxy-1,3-dihydroisoindol-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-6-trifluoromethanesulfonyloxy-1,3-dihydroisoindol-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-6-propargyloxy-1,3-dihydroisoindol-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-6-nitro-1,3-dihydroisoindol-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-6-(isoindoline-1,3-dione-2-yl)-1,3-dihydroisoindol-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5-bromo-1,3-dihydroisoindol-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5-methyl-1,3-dihydroisoindol-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5-hydroxy-1,3-dihydroisoindol-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5-methoxy-1,3-dihydroisoindol-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5-acetoxy-1,3-dihydroisoindol-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5-propargyloxy-1,3-dihydroisoindol-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-4-hydroxy-1,3-dihydroisoindol-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-4-methoxy-1,3-dihydroisoindol-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-4-acetoxy-1,3-dihydroisoindol-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-4-trifluoromethanesulfonyloxy-1,3-dihydroisoindol-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-4-propargyloxy-1,3-dihydroisoindol-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-4-nitro-1,3-dihydroisoindol-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5-fluoro-6-nitro-1,3-dihydroisoindol-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5,6-dibromo-4-methoxy-1,3-dihydroisoindol-1-one, N-[2-(N-trifluoromethanesulfonyl)amino-5-trifluoromethyl-benzyl]-1,3-dihydroisoindol-1-one, N-[2-(N-trifluoromethanesulfonyl)amino-5-trifluoromethyl-benzyl]-5-bromo-1,3-dihydroisoindol-1-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-1,3-dihydroisoindol-1-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-7-amino-1,3-dihydroisoindol-1-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-5-bromo-1,3-dihydroisoindol-1-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)amino-5-trifluoromethyl-benzyl]-1,3-dihydroisoindol-1-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)amino-5-trifluoromethyl-benzyl]-5-bromo-1,3-dihydroisoindol-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-methoxymethyloxy-1,3-dihydroisoindol-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-8-fluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-8-chloro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-8-bromo-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-8-iodo-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-8-methyl-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-8-cyclopropyl-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-8-phenyl-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-8-trifluoromethyl-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-8-cyano-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-8-hydroxy-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-8-methoxy-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-8-acetoxy-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-8-difluoromethoxy-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-8-trifluoromethoxy-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-8-propargyloxy-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-8-dimethylamino-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-8-methoxycarbonyl-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-fluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-chloro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-bromo-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-iodo-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-methyl-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-ethyl-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-tertiary-butyl-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-phenyl-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-trifluoromethyl-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-nitro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-hydroxy-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-methoxy-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-ethoxycarbonyloxy-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-benzoyloxy-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-propargyloxy-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-trifluoromethoxy-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-6-fluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-6-chloro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-6-bromo-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-6-iodo-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-6-methyl-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-6-trifluoromethyl-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-6-methoxy-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5-fluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5-chloro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5-methyl-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5-nitro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5-methoxy-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5-acetoxy-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5-methanesulfonyloxy-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5-trifluoromethoxy-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5-ethoxycarbonyloxy-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5-benzoyloxy-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5-propargyloxy-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-8-fluoro-7-methyl-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-8-fluoro-7-nitro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7,8-dichloro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-8-chloro-7-methyl-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-6,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-8-fluoro-6-methyl-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-6-cyclopropyl-8-fluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-6-cyano-8-fluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-6,8-dichloro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-6,8-dimethyl-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5-chloro-8-fluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5-bromo-8-fluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-8-fluoro-5-methyl-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-8-fluoro-5-trifluoromethyl-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-8-fluoro-5-methoxy-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5-chloro-8-fluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5,8-dichloro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5-fluoro-8-hydroxy-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5-fluoro-8-methoxy-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5-fluoro-8-methanesulfonyloxy-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5-fluoro-8-dimethylamino-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5-fluoro-8-(N-morpholinyl)-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5-fluoro-8-methylthio-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5-fluoro-8-methanesulfonyl-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5,8-bis(methanesulfonyl)-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-6,7-dichloro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-6-fluoro-7-methyl-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-6-chloro-7-methyl-3,4-dihydroisoquinolin-1(2H)-one,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-6-fluoro-7-nitro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-6-chloro-7-nitro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5,6-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-6,8-difluoro-7-nitro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-6,8-dichloro-7-nitro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-3,4-dihydrobenzo[h]isoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-3,4-dihydrobenzo[g]isoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7,8-dihydrothiazolo[4,5-h]isoquinolin-9(6H)-one, N-[2-(N-methyl-N-trifluoromethanesulfonyl)aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-propargyl-N-trifluoromethanesulfonyl)aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-(4-methoxybenzyl)-N-trifluoromethanesulfonyl)aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-[3-(1,3-dioxane-2-yl)propanyl]-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-cyanomethyl-N-trifluoromethanesulfonyl)aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-ethoxymethyl-N-trifluoromethanesulfonyl)aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(isopropyloxycarbonyloxymethyl)-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-acetyl-N-trifluoromethanesulfonyl)aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-ethylcarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(1-propylcarbonyl)-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(2-propylcarbonyl)-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(2-methyl-1-propylcarbonyl)-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(2,2-dimethyl-1-propylcarbonyl)-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-chloromethylcarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-cyclopropylcarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-8-fluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-cyclopropylcarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-8-chloro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-cyclopropylcarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-6-chloro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-cyclopropylcarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-cyclopropylcarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-8-fluoro-5-methyl-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(2-methyl-cyclopropyl)carbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(2,2-dimethyl-cyclopropyl)carbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(2,2-dichloro-1-methyl-cyclopropyl)carbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-cyclobutylcarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-cyclopentylcarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-cyclohexylcarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-acryloyl-N-trifluoromethanesulfonyl)aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(prop-1-en-1-yl)carbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(2-methyl-prop-1-en-1-yl)carbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(prop-1-en-2-yl)carbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(3-ethoxyacryloyl)-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-benzoyl-N-trifluoromethanesulfonyl)aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(furan-2-yl)carbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(thiophen-2-yl)carbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(1-methyl-1H-pyrrol-2-yl)carbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(furan-3-yl)carbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(tetrahydrofuran-2-yl)carbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(tetrahydrofuran-3-yl)carbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(tetrahydropyran-4-yl)carbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(2-cyclopropylacetyl)-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(2-hydroxyethyl)carbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-methoxyacetyl-N-trifluoromethanesulfonyl)aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-ethoxyacetyl-N-trifluoromethanesulfonyl)aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(2-methoxyethyl)carbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(2-tert-butyldimethylsilyloxyethyl)carbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-acetoxyacetyl-N-trifluoromethanesulfonyl)aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-methylsulfylacetyl-N-trifluoromethanesulfonyl)aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-ethylsulfylacetyl-N-trifluoromethanesulfonyl)aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(1-methylsulfilethyl)carbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-methoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-8-fluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-8-cyclopropyl-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-8-cyano-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-8-hydroxy-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-8-phenyl-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-5-methyl-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-8-fluoro-6-methyl-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-6-cyclopropyl-8-fluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-6-cyano-8-fluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-5-bromo-8-fluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-8-fluoro-5-methyl-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-8-fluoro-5-trifluoromethyl-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-8-fluoro-5-methoxy-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-8-chloro-5-fluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-8-dimethylamino-5-fluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-5-fluoro-8-(N-morpholinyl)-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-5-fluoro-8-methylthio-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-5,8-bis(methylthio)-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-5-fluoro-8-methanesulfonyl-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-5,6-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(1-propyl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(2-propyl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(1-butyl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(2-methyl-1-propyl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(2-butyl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(1,1-dimethyl-ethyl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(1-pentyl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(1-hexyl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(1-heptyl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(2,2-dimethyl-1-propyl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(chloromethyl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(trichloromethyl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(1-chloroethyl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(2-fluoroethyl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-8-fluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(2-fluoroethyl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(2,2-difluoroethyl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(2,2-difluoroethyl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-8-fluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(2,2-difluoroethyl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(2,2,2-trifluoroethyl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(2-chloroethyl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(2,2-difluoro-1-methyl-ethyl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(2,2,2-trifluoro-1-methyl-ethyl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(1,3-difluoropropan-2-yl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-cyclopropyloxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-cyclobutyloxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-cyclopentyloxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-cyclohexyloxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-allyloxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(but-3-en-2-yl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(2-methylallyl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(3-methylbut-2-en-1-yl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-propargyloxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(but-3-yn-2-yl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-phenoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(4-nitro-phenoxy)carbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(oxetan-3-yl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(oxetan-3-yl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-8-fluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(oxetan-3-yl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(tetrahydrofuran-3-yl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(tetrahydrofuran-3-yl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-((S)-tetrahydrofuran-3-yl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-((R)-tetrahydrofuran-3-yl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(tetrahydrothiophen-3-yl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(1,1-dioxidotetrahydrothiophen-3-yl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(tetrahydro-2H-pyran-3-yl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(tetrahydro-2H-pyran-4-yl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(1,3-dioxan-5-yl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(2,2-dimethyl-1,3-dioxan-5-yl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(tetrahydro-2H-thiopyran-4-yl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(1,1-dioxidetetrahydro-2H-thiopyran-4-yl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(2,5-dioxopyrrolidin-1-yl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(cyclopropylmethyloxy)carbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-benzyloxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(oxiran-2-ylmethyl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-[(2-methyloxiran-2-yl)methyl]oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-[(3,3-dimethyloxiran-2-yl)methyl]oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-[1-(oxiran-2-yl)ethyl]oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(oxetan-2-ylmethyl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-(oxetan-3-ylmethyl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-[(tetrahydrofuran-2-yl)methyl]oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-[(tetrahydrofuran-3-yl)methyl]oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-[(tetrahydro-2H-pyran-2-yl)methyl]oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-[(tetrahydro-2H-pyran-4-yl)methyl]oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-[(2-oxo-1,3-dioxolan-4-yl)methyl]oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-[(5-methyl-2-oxo-1,3-dioxol-4-yl)methyl]oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(2-cyano-ethoxy)carbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(2-hydroxy-ethoxy)carbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(2-methoxy-ethoxy)carbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(1-methyl-2-methoxy-ethoxy)carbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(1,3-dimethoxypropan-2-yl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-[2-(tert-butyldiphenylsilyloxy)ethyl]oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-[2-(acetyloxy)ethoxy]carbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-[2-(methanesulfonyloxy)ethoxy]carbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(2-oxopropyl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(methoxycarbonylmethoxycarbonyl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(2-methylthio-ethoxy)carbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(2-methanesulfonyl-ethoxy)carbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(2-propylthio)carbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(2-propylthio)carbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-8-fluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-ethylthio-carbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(2-propylthio)carbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(2-butyl)thio-carbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-methylaminocarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N-(2-propylamino)carbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-dimethylaminocarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-methanesulfonyl-N-trifluoromethanesulfonyl)aminobenzyl]-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-methanesulfonyl-N-trifluoromethanesulfonyl)aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-methanesulfonyl-N-trifluoromethanesulfonyl)aminobenzyl]-5-fluoro-8-hydroxy-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-ethanesulfonyl-N-trifluoromethanesulfonyl)aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N,N-bis(trifluoromethanesulfonyl)]aminobenzyl]-8-hydroxy-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N,N-bis(trifluoromethanesulfonyl)]aminobenzyl]-8-propargyloxy-3,4-dihydroisoquinolin-1(2H)-one, N-[2-[N,N-bis(trifluoromethanesulfonyl)]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-cyclopropanesulfonyl-N-trifluoromethanesulfonyl)aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, sodium [2-[(5,8-difluoro-1-oxo-3,4-dihydroisoquinolin-2(1H)-yl)methyl]phenyl][(trifluoromethyl)sulfonyl]amide, potassium [2-[(5,8-difluoro-1-oxo-3,4-dihydroisoquinolin-2(1H)-yl)methyl]phenyl][(trifluoromethyl)sulfonyl]amide, N-[2-(N-trifluoromethanesulfonyl)amino-3-chloro-benzyl]-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)amino-4-methyl-benzyl]-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)amino-4-methoxy-benzyl]-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)amino-5-fluoro-benzyl]-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)amino-5-chloro-benzyl]-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)amino-5-bromo-benzyl]-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)amino-5-methyl-benzyl]-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)amino-6-chloro-benzyl]-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)amino-3,5-dichloro-benzyl]-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)amino-5-chloro-benzyl]-8-chloro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)amino-5-chloro-benzyl]-6-chloro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)amino-3-fluoro-benzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)amino-3-chloro-benzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)amino-3-methyl-benzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)amino-4-fluoro-benzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)amino-5-fluoro-benzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)amino-5-chloro-benzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)amino-5-methyl-benzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)amino-5-hydroxy-benzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)amino-5-methoxy-benzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)amino-6-fluoro-benzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)amino-6-chloro-benzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)amino-6-methyl-benzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)amino-naphthalen-3-yl-methyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)amino-5-chloro-benzyl]-8-chloro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)amino-3-fluoro-benzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)amino-3-chloro-benzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)amino-3-methyl-benzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)amino-4-fluoro-benzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)amino-5-fluoro-benzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)amino-5-chloro-benzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)amino-5-methyl-benzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)amino-5-trifluoromethyl-benzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)amino-5-hydroxy-benzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)amino-5-methoxy-benzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)amino-6-fluoro-benzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)amino-6-chloro-benzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)amino-6-methyl-benzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)amino-naphthalen-3-yl-methyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-pent-1-yloxycarbonyl-N-trifluoromethanesulfonyl)amino-4-fluoro-benzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-pent-1-yloxycarbonyl-N-trifluoromethanesulfonyl)amino-5-fluoro-benzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-pent-1-yloxycarbonyl-N-trifluoromethanesulfonyl)amino-6-fluoro-benzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-2,3,4,5-tetrahydro-1H-2-benzazepin-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-9-chloro-2,3,4,5-tetrahydro-1H-2-benzazepin-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-9-methyl-2,3,4,5-tetrahydro-1H-2-benzazepin-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-fluoro-2,3,4,5-tetrahydro-1H-2-benzazepin-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-chloro-2,3,4,5-tetrahydro-1H-2-benzazepin-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-methyl-2,3,4,5-tetrahydro-1H-2-benzazepin-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-4,5-dihydro-6H-thieno[2,3-c]pyrrol-6-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-2-bromo-4,5-dihydro-6H-thieno[2,3-c]pyrrol-6-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-2-(methylthio)-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-5-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5,6-dihydrofurano[2,3-c]pyrimidin-7(4H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5,6-dihydrothieno[2,3-c]pyridin-7(4H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-6,7-dihydrothieno[3,2-c]pyridin-4(5H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-3-methyl-5,6-dihydroisoxazolo[5,4-c]pyridin-7(4H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-2-methyl-6,7-dihydrooxazolo[5,4-c]pyridin-4(5H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-6,7-dihydrooxazolo[4,5-c]pyridin-4(5H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-2-methyl-6,7-dihydrooxazolo[4,5-c]pyridin-4(5H)-one, 5-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-1,5,6,7-tetrahydro-4H-pyrazolo[4,3-c]pyridin-4-one, 5-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-1-methyl-1,5,6,7-tetrahydro-4H-pyrazolo[4,3-c]pyridin-4-one, 5-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-3-bromo-1-methyl-1,5,6,7-tetrahydro-4H-pyrazolo[4,3-c]pyridin-4-one, 5-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-3-methyl-1-phenyl-1,5,6,7-tetrahydro-4H-pyrazolo[4,3-c]pyridin-4-one, 5-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-3-methyl-1-(pyridin-2-yl)-1,5,6,7-tetrahydro-4H-pyrazolo[4,3-c]pyridin-4-one, 5-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-2-methyl-2,5,6,7-tetrahydro-4H-pyrazolo[4,3-c]pyridin-4-one, 5-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-2,3-dimethyl-2,5,6,7-tetrahydro-4H-pyrazolo[4,3-c]pyridin-4-one, 5-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-3-bromo-2-methyl-2,5,6,7-tetrahydro-4H-pyrazolo[4,3-c]pyridin-4-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-6,7-dihydro-1,7-naphthyridin-8(5H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-3,4-dihydro-2,6-naphthyridin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-2-methyl-7,8-dihydropyrido[4,3-d]pyrimidin-5(6H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-5,6-dihydrothieno[2,3-c]pyridin-7(4H)-one, 5-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-3-bromo-1-methyl-1,5,6,7-tetrahydro-4H-pyrazolo[4,3-c]pyridin-4-one, 5-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-2,3-dimethyl-2,5,6,7-tetrahydro-4H-pyrazolo[4,3-c]pyridin-4-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-6,7-dihydro-1,7-naphthyridin-8(5H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-3,4-dihydro-2,6-naphthyridin-1(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-7,8-dihydro-1,6-naphthyridin-5(6H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-3,4-dihydroisoquinoline-1(2H)-thione, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-thione, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-3-methyl-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-3,3-dimethyl-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-2,2-dimethyl-2,3-dihydro-4H-benzo[e][1,3]oxazin-4-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-1H-benzo[d][1,2]oxazin-4(3H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-2,3-dihydro-4H-benzo[e][1,3]thiazin-4-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-4-methyl-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-4-methyl-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-4,4-dimethyl-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-4-methoxyisoquinolin-1(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethylsulfonyl)aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-thione, N-[2-(N-ethoxycarbonyl-N-trifluoromethylsulfonyl)aminobenzyl]-3-methyl-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethylsulfonyl)aminobenzyl]-1H-benzo[d][1,2]oxazin-4(3H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethylsulfonyl)aminobenzyl]-4-methyl-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethylsulfonyl)aminobenzyl]-4,4-dimethyl-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethylsulfonyl)aminobenzyl]-isoquinolin-1(2H)-one, N-[2-(N-trifluoromethylsulfonyl)amino-phenylethan-1-yl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-difluoromethanesulfonyl)aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-1,3-dihydroindol-2-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5-fluoro-1,3-dihydroindol-2-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5-chloro-1,3-dihydroindol-2-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5-bromo-1,3-dihydroindol-2-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-6-chloro-1,3-dihydroindol-2-one, N-[2-(N-trifluoromethanesulfonyl)amino-5-trifluoromethyl-benzyl]-1,3-dihydroindol-2-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-1,3-dihydroindol-2-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-5-fluoro-1,3-dihydroindol-2-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-5-chloro-1,3-dihydroindol-2-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-5-bromo-1,3-dihydroindol-2-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-6-chloro-1,3-dihydroindol-2-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)amino-5-trifluoromethyl-benzyl]-1,3-dihydroindol-2-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-1,4-dihydroisoquinolin-3(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-3,4-dihydroquinolin-2(1H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-3-methyl-3,4-dihydroquinazolin-2(1H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-phenanthridin-6(5H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-1,4-dihydroisoquinolin-3(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-3,4-dihydroquinolin-2(1H)-one, 1-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-3-methyl-3,4-dihydroquinazolin-2(1H)-one, and The herbicidal composition according to claim 1, wherein the herbicidal agent is selected from the group consisting of N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-phenanthridin-6(5H)-one.

8. The herbicidal composition according to any one of claims 1 to 7, wherein the compound represented by the formula [1] is a mixture of enantiomers or a mixture of diastereoisomers.

9. A herbicidal composition according to any one of claims 1 to 7, wherein the component (b) comprises at least one member selected from the group consisting of an ALS inhibitor, a germination / elongation suppressor, a photosynthesis inhibitor, a PPO inhibitor, a bleaching agent, a VLCFAs inhibitor, a hormone action inhibitor / disruptor, and an ACCase inhibitor.

10. The ALS inhibitor is selected from the group consisting of amidosulfuron, azimsulfuron, bensulfuron-methyl, bispyribac, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cloransulam-methyl, cyclosulfamuron, diclosulfamuron, cyclo ... Diclosulam, ethametsulfuron-methyl, ethoxysulfuron, flazasulfuron, florasulam, flucarbazone, flumetsulam, flupyrsulfuron-methyl, foramsulfuron, halosulfuron-methyl n-methyl, imazamethabenz-methyl, imazamox, imazapic, imazapyr, imazaquin, imazethapyr, imazosulfuron, iodosulfuron-methyl, iofensulfuron, iofensulfuron sodium sodium), metazosulfuron, metsulfuron-methyl, nicosulfuron, orthosulfamuron, oxasulfuron, penoxsulam, primisulfuron-methyl, propoxycarbazone, propyrisulfuron,Prosulfuron, pyrazosulfuron-ethyl, pyribenzoxim, pyriftalid, pyriminobac-methyl, pyrimisulfan, pyrithiobac, rimsulfuron, sulfometuron-methyl, sulfosulfuron, chienka At least one selected from the group consisting of thiencarbazone-methyl, thifensulfuron-methyl, triafamone, triasulfuron, tribenuron-methyl, trifloxysulfuron, triflusulfuron-methyl, and tritosulfuron; The germination and elongation inhibitor is selected from the group consisting of benfluralin, bromobutide, butamifos, butralin, carbetamide, chlorpropham, chlorthal-dimethyl, cumyluron, dichlobenil, dinitramine, dithiopyr, and dimethicone. dymron, ethalfluralin, etobenzanide, methiozolin, methyldymron, oryzalin, oxaziclomefone, pendimethalin, propham, propyzamide, pyributicarb, sodium chlorate,The present invention relates to a method for producing a plant-derived insecticide comprising the steps of: (a) detecting a plant-derived insecticide comprising: a photochemically inhibiting agent comprising at least one selected from the group consisting of tetflupyrolimet, thiazopyr, triaziflam, and trifluralin; and (b) detecting a plant-derived insecticide comprising at least one selected from the group consisting of ametryn, atrazine, bentazon, bromacil, bromoxynil, bromofenoxim, chlorbromuron, chloridazon, chlorotoluron, chloroxuron, and cyanazine. , desmedipham, desmetryn, dimefuron, dimethametryn, diuron, ethidimuron, fenuron, fluometuron, hexazinone, ioxynil, isoproturon, isouron, Carbutilate, lenacil, linuron, metamitron, methabenzthiazuron, metobromuron, metoxuron, metribuzin, monolinuron, neburon, pentanochlor, phenmede phenmedipham, prometon, prometryn, propanil, propazine, pyridafol, pyridate, quinoclamin, siduron, simazine, simetryn, tebuthiuron, terbacil,At least one selected from the group consisting of terbumeton, terbuthylazine, terbutryn, and trietazine; The PPO inhibitor is selected from the group consisting of acifluorfen, azafenidine, benzfendizone, bifenox, butafenacil, carfentrazone-ethyl, chlomethoxyfen, chlorphthalim, cinidon-ethyl, cyclopyranil, fluazolate, flufenpyr-ethyl, flumiclorac-pentyl, flumioxazin, fluoroglycophen ... Fluoroglycofen-ethyl, fluthiacet-methyl, fomesafen, halosafen, lactofen, oxadiazon, oxadiargyl, oxyfluorfen, pentose At least one selected from the group consisting of pentoxazone, profluazol, pyraclonil, pyraflufen-ethyl, saflufenacil, sulfentrazone, and thidiazimin; The whitening agent is selected from the group consisting of aclonifen, amitrole, beflubutamid, benzobicyclon, benzofenap, bicyclopyrone, clomazone, cyclopyrimorate,Diflufenican, fenquinotrione, fluridone, flurochloridone, flurtamone, iptriazopyride, isoxachlortole, isoxaflutole, mesotrione, norflurazo at least one selected from the group consisting of norflurazon, picolinafen, pyrasulfotole, pyrazolate, pyrazoxyfen, sulcotrione, tefuryltrione, tembotrione, and topramezone; The VLCFAs inhibitors include acetochlor, alachlor, anilofos, benfuresate, butachlor, butyrate, cafenstrole, dimepiperate, dimesulfazet, dimethachlor, dimethenamid, dimethenamid-P, EPTC, esprocarb, etofumes, ethofumesate, fenoxasulfone, fentrazamide, flufenacet, hexylthiocarbam, indanofan, ipfencarbazone, mefenacet, metazachlor, molinate, orbencarb, pebulate, pesoxamid, piperophos,At least one selected from the group consisting of pretilachlor, propachlor, propisochlor, prosulfocarb, pyroxasulfone, S-metolachlor, thenylchlor, thiobencarb, thiocarbazil, triallate, and vernolate; The hormone action inhibitors and disruptors include 2,3,6-TBA, 2,4-D, 2,4-DB, 2,4-PA-ethyl, aminocyclopyrachlor, aminopyralid, benazolin, chloramben, clomeprop, clopyralid, dicamba, dichlorprop, and diflufenzopyr. , florpyrauxifen-benzyl, fluroxypyr-1-methylheptylester, MCPA, MCPB, mecoprop, naptalam, phenothiol, picloram, quinclorac, quinmerac, and triclopyr; The ACCase inhibitor is selected from the group consisting of alloxydim, butroxydim, clethodim, clodinafop-propargyl, cycloxydim, cyhalofop-butyl, diclofop-methyl, fenoxaprop-P-ethyl,10. The herbicidal composition according to claim 9, comprising at least one member selected from the group consisting of fluazifop-P-butyl, haloxyfop-P-methyl, metamifop, pinoxaden, profoxydim, propaquizafop, quizalofop-P-ethyl, sethoxydim, tepraloxydim, and tralkoxydim.

11. The ALS inhibitor includes at least one selected from the group consisting of bispyribac, metazosulfuron, penoxsulam, pyrimisulfan, propyrisulfuron, sulfometuron-methyl, and triafamone, and the germination and elongation inhibitor includes bromobutide, dymron, methiozolin, sodium chlorate, or the like. the photosynthesis inhibitor comprises at least one selected from the group consisting of bentazone, carbutilate, and propanil; the PPO inhibitor comprises at least one selected from the group consisting of carfentrazone-ethyl, cyclopyranil, oxadiargyl, pentoxazone, and pyraclonil; The whitening agent includes at least one selected from the group consisting of benzobicyclon, clomazone, cyclopyrimorate, fenquinotrione, iptriazopyrid, mesotrione, and tefuryltrione;The VLCFAs inhibitor comprises at least one selected from the group consisting of benfuresate, cafenstrole, dimesulfazet, fenoxasulfone, fentrazamide, ipfencarbazone, and thenylchlor, and the hormone action inhibitor / disruptor comprises at least one selected from the group consisting of florpyrauxifen-benzyl and quinclorac, 11. The herbicidal composition according to claim 10, wherein the ACCase inhibitor comprises at least one selected from the group consisting of cyhalofop-butyl and metamifop.

12. The herbicidal composition according to any one of claims 1 to 7, which is used as an agricultural and horticultural herbicide.

13. A method for controlling plant pests, comprising a step of applying (a) a compound represented by formula [1] according to claim 1 or a salt thereof, and (b) an agricultural or horticultural herbicide to a plant or an area surrounding the plant in an agricultural or non-agricultural land, wherein the component (a) and the component (b) are applied simultaneously, successively, or separately.

14. The method for controlling plant pests according to claim 13, wherein the treatment is at least one selected from the group consisting of spraying, dusting, dusting, spraying, diffusing, dipping, irrigating, injecting, watering (immersion), foaming, applying, dusting, coating, spraying, fumigating, smoking, fog and painting.

15. The method for controlling plant pests according to claim 13 or 14, wherein the area around the plant is at least one selected from the group consisting of soil, water for hydroponic cultivation, and cultivation materials.