Haloalkyl sulfone anilide compound and herbicide containing same

Abstract

The present invention is a novel haloalkyl sulfone anilide compound or a salt thereof, an herbicide composition including said compound or salt thereof, an herbicide method including a step for applying the herbicide composition, and a method for manufacturing said compound.

Description

Haloalkylsulfonanilide compounds and herbicides containing them

[0001] The present invention relates to a novel haloalkylsulfonanilide compound or a salt thereof, a herbicide containing the compound or salt as an active ingredient, and a method for using the same.

[0002] It has been reported that compounds having a haloalkylsulfonylamino group at the 2-position of a benzyl group have herbicidal activity (Patent Documents 1 to 13).

[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 2014 / 175206, International Publication No. WO 2015 / 004282, International Publication No. WO 2015 / 097071, International Publication No. WO 2016 / 056565, International Publication No. WO 2016 / 207081, International Publication No. WO 2016 / 207082, International Publication No. WO 2016 / 207083

[0004] Currently, many herbicides have been developed and are in use, but there are many types of weeds to be controlled, and therefore the development of herbicidal compounds with a broader herbicidal spectrum, high activity, and high safety is desired.

[0005] The present inventors have conducted extensive research to create novel and useful compounds that are more effective as herbicides and have a higher level of safety, and as a result have now discovered novel haloalkylsulfonanilide compounds that have excellent biological activity, and have completed the present invention based on this finding.

[0006] The present invention includes the disclosure of the following compound: (1) General Formula [1]

[0007]

[0008] 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 ~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(C１ ~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 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 ~C６ 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 (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, halo C 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 ６alkoxy)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 ２ phenylsulfonyl 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 ６ alkyl)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 from２ 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 ~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 C１ ~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(C １ ~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 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 and R may be interrupted by one or two heteroatoms selected from the group consisting of cycloalkyl, and may form an optionally substituted 3- to 7-membered ring or may form an olefin, 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 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 and wherein the carbocyclic or heterocyclic ring is optionally substituted with one or more halogen atoms.

[0009] (2) General formula [1a]

[0010]

[0011] {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 ~C６ 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, 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.

[0012] (3) General formula [1a]

[0013]

[0014] {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 ~C６ 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(C１ ~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 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(C１ ~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 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 ~C６ 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, 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 , X ２ , X ３ and X ４ may be taken together with adjacent carbon 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 contains one or two 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 Y３ , 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-dioxolanyl, 2-oxo-1,3-dioxolyl, or 2,5-dioxopyrrolidinyl.

[0015] (4) 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 (C１ ~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 chloro atom, or methyl; X ２ and X ３ is a hydrogen atom, and X ４ is a hydrogen atom, a fluorine atom, a chloro atom, methyl, trifluoromethyl, or methoxy; Y １ , Y ２ , Y ３ and Y ４ is a hydrogen atom, and the heterocyclyl is oxiranyl, oxetanyl, tetrahydrofuranyl, or tetrahydropyranyl, or a salt thereof.

[0016] (5) General formula [1b]

[0017]

[0018] {wherein Het is

[0019]

[0020] 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 , Y２ , Y ３ and Y ４ is a hydrogen atom} or a salt thereof.

[0021] (6) 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 (5) The compound or salt thereof according to (5), wherein the aryl group is aryl)carbonyl.

[0022] (7) 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-3,44-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-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)-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-3,44-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 compound or salt thereof according to (1), selected from the group consisting of N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-phenanthridin-6(5H)-one.

[0023] (8) The compound or salt thereof according to any one of (1) to (7), wherein the compound represented by formula [1] is a mixture of enantiomers or a mixture of diastereoisomers.

[0024] (9) A composition having herbicidal activity, which contains the compound represented by formula [1] or a salt thereof according to any one of (1) to (8) as an active ingredient.

[0025] (10) A method for herbicidal control, comprising treating soil and / or plants with an effective amount of the composition according to (9).

[0026] (11) A method for controlling weeds in paddy fields, which comprises treating paddy field soil with an effective amount of the composition according to (9).

[0027] The haloalkylsulfonanilide compound of the present invention represented by formula [1] or an agriculturally acceptable salt thereof exhibits high herbicidal activity and, further, high safety to useful plants, useful crops, etc., and thus has excellent effects as an agricultural chemical.

[0028] The present invention will be described in detail below. The haloalkylsulfonanilide compound of the present invention includes not only the haloalkylsulfonanilide compound represented by formula [1], but also salts, hydrates, solvates, and polymorphic substances of the compound, as well as N-oxides of the haloalkylsulfonanilide compound represented by formula [1]. The salt is not particularly limited, and examples thereof include salts acceptable for agricultural chemical production, specifically sodium salts, potassium salts, magnesium salts, calcium salts, and aluminum salts. Furthermore, all possible stereoisomers or optical isomers of the compound 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 the compound of the present invention (the haloalkylsulfonanilide compound represented by formula [1]). Formula [1] provides a specific definition of the haloalkylsulfonanilide compound 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.

[0029] 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.

[0030] 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 ４alkenyl)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 ３ alkoxy)carbonyl, heterocyclyloxycarbonyl, heterocyclyl (C １ ~C ２ alkoxy)carbonyl, or methanesulfonyl.

[0031] 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.

[0032] 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 C １ ~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 C１ ~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 ６ Cycloalkyl)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 ６Alkylthio 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 C １ ~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:

[0033] 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.

[0034] 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.

[0035] Z ３ is preferably a halogen atom, triC １ ~C ６ Alkylsilyl, C １ ~C ６ 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.

[0036] 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.

[0037] Z ７ is preferably a halogen, C １ ~C ６ Alkyl, C３ ~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.

[0038] Z ８ is preferably Z ２ phenylthio 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:

[0039] 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.

[0040] X １ is preferably a hydrogen atom, halogen, methyl, trifluoromethyl, or methoxy, and more preferably a fluorine atom or a chloro 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. ４is preferably a hydrogen atom, halogen, methyl, trifluoromethyl, or methoxy, and more preferably a hydrogen atom, a fluorine atom, or a chloro atom.

[0041] Preferably, Y's are each independently a hydrogen atom, halogen, methyl, or trifluoromethyl, and more preferably a hydrogen atom.

[0042] 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.

[0043] 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.

[0044] 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.

[0045] 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 R２ 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 ２ represents (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 chloro 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 X１ 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 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 represents a fluorine atom, and X ２ and X ３ represents a hydrogen atom, and X ４ represents a chloro atom}. 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 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 ４represents 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 , 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 represents a chloro 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}.

[0046] In this specification, the following symbols have the following meanings: i: iso, s: secondary, t: tertiary, c: cyclo, p: para.

[0047] The terms used in this specification are explained below. １ ~C ６ The notation with an element symbol and a subscript number such as C 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.

[0048] Examples of halogen include fluorine, chlorine, bromine, and iodine atoms. In this specification, the term "halo" also refers to these halogens.

[0049] 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, each of which is selected within the range of the specified number of carbon atoms.

[0050] 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.

[0051] 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.

[0052] 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.

[0053] 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.

[0054] 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.

[0055] 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.

[0056] Cycloalkyl includes cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc., each selected from the range of carbon numbers specified.

[0057] 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.

[0058] Examples of cycloalkylalkyl include cyclopropylmethyl, 2-cyclopropylethyl, cyclopentylmethyl, cyclohexylmethyl, and the like, each selected from the range of carbon numbers specified.

[0059] Phenylalkyl and Z ２Examples 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.

[0060] Heterocyclylalkyl and Z ２ Heterocyclyl C substituted by one or more substituents selected from １ ~C ６ Examples 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.

[0061] Cyanoalkyl includes cyanomethyl, 1-cyanoethyl, 2-cyanoethyl, etc., each selected from the range of carbon numbers specified.

[0062] 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.

[0063] Haloalkoxyalkyl includes fluoromethoxymethyl, chloromethoxymethyl, bromomethoxymethyl, 2,2,2-trifluoroethoxymethyl, 2-(chloromethoxy)ethyl, and the like, each selected from the range of carbon numbers specified.

[0064] Examples of cycloalkyloxyalkyl include cyclopropyloxymethyl, 2-cyclopropyloxyethyl, cyclopentyloxymethyl, cyclohexyloxymethyl, and the like, each selected from the range of carbon numbers specified.

[0065] 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.

[0066] Phenylalkoxyalkyl and Z ２Examples 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.

[0067] 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.

[0068] Phenylcarbonyloxyalkyl and Z ２ Examples 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.

[0069] 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.

[0070] 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.

[0071] 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.

[0072] Phenylcarbonyloxyalkoxyalkyl and Z ２Examples 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.

[0073] 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.

[0074] 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.

[0075] Examples of cycloalkylcarbonyloxyalkyl include cyclopropanecarbonyloxymethyl, cyclobutanecarbonyloxymethyl, cyclopentanecarbonyloxymethyl, 2-(cyclohexanecarbonyloxy)ethyl, and the like, each selected from the range of carbon numbers specified.

[0076] 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.

[0077] Phenoxycarbonyloxyalkyl and Z ２ Examples 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.

[0078] 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.

[0079] 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.

[0080] Phenylaminocarbonyloxyalkyl and Z ２ Examples 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.

[0081] Alkyl(phenyl)aminocarbonyloxyalkyl and alkyl(Z ２ Examples 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.

[0082] 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.

[0083] 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.

[0084] 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.

[0085] 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.

[0086] 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.

[0087] 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.

[0088] Phenylthioalkyl and Z ２ Examples 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.

[0089] 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.

[0090] 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.

[0091] 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.

[0092] 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.

[0093] 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.

[0094] The thiocyanatoalkyl includes cyanothiomethyl, 1-(cyanothio)ethyl, 1-(cyanothio)ethyl, and the like, each selected from the range of carbon numbers specified.

[0095] 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.

[0096] 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.

[0097] 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.

[0098] 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.

[0099] 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.

[0100] 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.

[0101] 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.

[0102] Examples of cycloalkylcarbonyl include cyclopropanecarbonyl, cyclobutanecarbonyl, cyclopentanecarbonyl, cyclohexanecarbonyl, and the like, each selected from the range of carbon numbers specified for that group.

[0103] 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.

[0104] 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.

[0105] 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.

[0106] 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.

[0107] 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.

[0108] 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.

[0109] 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.

[0110] 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.

[0111] 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.

[0112] 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.

[0113] Examples of the cycloalkylalkylcarbonyl include cyclopropylmethylcarbonyl, 2-cyclopropylethylcarbonyl, cyclopentylmethylcarbonyl, cyclohexylmethylcarbonyl, and the like, each selected from the range of carbon numbers specified.

[0114] 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.

[0115] Heterocyclylalkylcarbonyl and Z ２ The heterocyclylalkylcarbonyl substituted by one or more substituents selected from (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, (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, Examples include methylcarbonyl, (pyridin-3-yl) methylcarbonyl, (pyridin-4-yl) oxycarbonyl, and the like, each selected from the range of carbon numbers specified for each.

[0116] 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.

[0117] 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.

[0118] 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.

[0119] 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.

[0120] 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.

[0121] 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.

[0122] 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.

[0123] 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.

[0124] 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.

[0125] 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.

[0126] 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.

[0127] 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.

[0128] 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.

[0129] 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.

[0130] 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.

[0131] Examples of the cycloalkyloxycarbonyl include cyclopropyloxycarbonyl, cyclobutyloxycarbonyl, cyclopentyloxycarbonyl, cyclohexyloxycarbonyl, and the like, each selected from the range of carbon numbers specified for that group.

[0132] 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.

[0133] 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.

[0134] 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.

[0135] 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.

[0136] 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.

[0137] Examples of the cycloalkylalkoxycarbonyl include cyclopropylmethoxycarbonyl, 2-cyclopropylethoxyoxycarbonyl, cyclopentylmethoxycarbonyl, and cyclohexylmethoxycarbonyl, each selected from the range of carbon numbers specified.

[0138] 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.

[0139] 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, and (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.

[0140] 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.

[0141] 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.

[0142] 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.

[0143] 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.

[0144] 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.

[0145] Examples of the alkyldiphenylsilyloxyalkoxycarbonyl include methyldiphenylsilyloxymethoxycarbonyl, ethyldiphenylsilyloxymethoxycarbonyl, and t-butyldiphenylsilyloxymethoxycarbonyl, each selected from the range of carbon numbers specified.

[0146] 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.

[0147] 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.

[0148] 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.

[0149] 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.

[0150] 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.

[0151] 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.

[0152] 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.

[0153] 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.

[0154] 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.

[0155] 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.

[0156] 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.

[0157] 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.

[0158] 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.

[0159] 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.

[0160] 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.

[0161] Examples of the alkoxyoxalyl include methoxycarbonylcarbonyl, ethoxycarbonylcarbonyl, i-propyloxycarbonylcarbonyl, t-butoxycarbonylcarbonyl, and the like, each selected from the range of carbon numbers specified.

[0162] Examples of alkylsulfonyl include methylsulfonyl, ethylsulfonyl, propylsulfonyl, i-propylsulfonyl, butylsulfonyl, i-butylsulfonyl, s-butylsulfonyl, and t-butylsulfonyl, each of which is selected from the range of carbon numbers specified.

[0163] 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.

[0164] Examples of cycloalkylsulfonyl include cyclopropanesulfonyl, cyclobutanesulfonyl, cyclopentanesulfonyl, cyclohexanesulfonyl, and the like, each selected from the range of carbon numbers specified for that group.

[0165] 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.

[0166] 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.

[0167] 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.

[0168] 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.

[0169] Examples of the cycloalkylalkylsulfonyl include cyclopropylmethylsulfonyl, 2-cyclopropylethylsulfonyl, cyclopentylmethylsulfonyl, cyclohexylmethylsulfonyl, and the like, each selected from the range of carbon numbers specified.

[0170] 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.

[0171] 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.

[0172] 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.

[0173] 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.

[0174] Examples of alkylthio include methylthio, ethylthio, propylthio, i-propylthio, butylthio, i-butylthio, s-butylthio, t-butylthio, and the like, each selected from the range of carbon numbers specified.

[0175] 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.

[0176] 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.

[0177] 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.

[0178] "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.

[0179] Examples of hydroxyalkyl include hydroxymethyl, 1-hydroxyethyl, 2-hydroxyethyl, 1-hydroxypropyl, 2-hydroxypropyl, 3-hydroxypropyl, 1-hydroxy-1-methylethyl, 2-hydroxy-1-methylethyl, 2-hydroxy-1,1-dimethylethyl, etc., each selected from the range of carbon numbers specified. Examples of monoalkylaminoalkyl include methylaminomethyl, ethylaminomethyl, propylaminomethyl, i-propylaminomethyl, butylaminomethyl, 2-(methylamino)ethyl, 2-(ethylamino)ethyl, 3-(methylamino)propyl, etc., each selected from the range of carbon numbers specified.

[0180] 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.

[0181] 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.

[0182] 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.

[0183] 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.

[0184] 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.

[0185] 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.

[0186] 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.

[0187] 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.

[0188] 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.

[0189] "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," which may be interrupted by one or two heteroatoms selected from the group consisting of R on the same carbon, and may be substituted by cycloalkyl. 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.

[0190] 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.

[0191] "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.

[0192] 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.

[0193] 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.

[0194] The cycloalkylalkyloxy includes cyclopropylmethoxy, 2-cyclopropylethoxy, cyclopentylmethoxy, cyclohexylmethoxy, and the like, each selected from the range of carbon numbers specified.

[0195] 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.

[0196] 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.

[0197] 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.

[0198] Examples of the alkoxycarbonyloxy include methoxycarbonyloxy, ethoxycarbonyloxy, propyloxycarbonyloxy, i-propyloxycarbonyloxy, and butyloxycarbonyloxy, each of which is selected from the range of carbon numbers specified.

[0199] Examples of alkylthiocarbonyloxy include methylthiocarbonyloxy, ethylthiocarbonyloxy, propylthiocarbonyloxy, i-propylthiocarbonyloxy, butylthiocarbonyloxy, i-butylthiocarbonyloxy, s-butylthiocarbonyloxy, and t-butylthiocarbonyloxy, and each is selected from the range of carbon numbers specified.

[0200] 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.

[0201] 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.

[0202] Dialkylphosphoroxy includes dimethylphosphoroxy, dimethylphosphoroxy, dipropylphosphoroxy, etc., each selected from the range of carbon numbers specified.

[0203] Examples of trialkylsilyloxy include trimethylsilyloxy, triethylsilyloxy, and t-butyldimethylsilyloxy, each selected from the range of carbon numbers specified.

[0204] 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.

[0205] 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.

[0206] Dialkylamino includes dimethylamino, diethylamino, ethyl(methyl)amino, methyl(propyl)amino, butyl(methyl)amino, etc., each selected from the range of carbon numbers specified.

[0207] 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.

[0208] 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.

[0209] 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.

[0210] "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.

[0211] "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.

[0212] "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.

[0213] 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.

[0214] Representative methods for producing the compound of the present invention represented by formula [1] 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 for the reaction.

[0215] <Production Method 1> The compound of the present invention represented by formula [1] can be produced by a method comprising the reaction scheme illustrated below.

[0216]

[0217] (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).

[0218] (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.

[0219] (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.

[0220] (Step 3) The compound represented by formula [5] is treated with a compound represented by general formula R １ SO ２ L １ Or (R １ SO２ ) ２ The compound represented by formula [6] can be produced by reacting a compound represented by formula R 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 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.

[0221] (Step 4) The compound represented by formula [6] is treated with a compound represented by general 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.

[0222] <Production Method 2> The compound of the present invention represented by formula [1] can also be produced by a method comprising the reaction scheme exemplified below.

[0223]

[0224] (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).

[0225] (Step 5) The compound represented by formula [5] is treated with a compound represented by general 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 1 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.

[0226] (Step 6) The compound represented by formula [7] is reacted with a compound represented by general formula R １ SO ２ L １ Or (R １ SO ２ ) ２The compound represented by formula [1] can be produced by reacting a compound represented by formula R 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 conventional method after the reaction is completed, and can be purified by column chromatography, recrystallization, or the like, if necessary.

[0227] <Production Method 3> The compound of the present invention represented by formula [6] can also be produced by a method comprising the reaction scheme illustrated below.

[0228]

[0229] (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).

[0230] (Step 7) The compound represented by formula [5] is treated with a compound represented by general formula R １ SO ２ L １ Or (R １ SO ２ ) ２ The compound represented by formula [8] can be produced by reacting a compound represented by formula R with a haloalkylsulfonyl derivative represented by formula [0] 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.

[0231] (Step 8) The compound represented by formula [8] is reacted with a compound represented by the general 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.

[0232] <Production Method 4> The compound of the present invention represented by formula [6] can also be produced by a method consisting of the reaction scheme exemplified below.

[0233]

[0234] (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).

[0235] (Step 9) The compound represented by formula [9] is treated with a compound represented by general formula R １ SO ２ L １ Or (R １ SO ２ ) ２The compound represented by formula

[10] can be produced by reacting a compound represented by formula R 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.

[0236] (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.

[0237] <Production Method 5> The compound of the present invention represented by the formula

[12] can be produced by a method comprising the reaction scheme illustrated below.

[0238]

[0239] (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).

[0240] (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.

[0241] <Intermediate Production Method 1> The intermediate compound represented by formula [3a] can be produced by a method represented by the reaction scheme shown below.

[0242]

[0243] (In the formula, X １ , X ２ , X ３ and X ４ are as defined in the above formula (1) [1]).

[0244] (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.

[0245] <Intermediate Production Method 2> The intermediate compound represented by formula [3b] can be produced by a method represented by the reaction scheme shown below.

[0246]

[0247] (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.

[0248] (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, if necessary, by column chromatography, recrystallization, or the like.

[0249] <Intermediate Production Method 3> The intermediate compound represented by formula [3c] can be produced by a method represented by the reaction scheme shown below.

[0250]

[0251] (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).

[0252] (Step 15) The compound represented by formula

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

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

[18] in a solvent in the presence or absence of a base.８ OC(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.

[0253] (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.

[0254] <Intermediate Production Method 4> The intermediate compound represented by formula [5a] can be produced by a method represented by the reaction scheme shown below.

[0255]

[0256] (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).

[0257] (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.

[0258] (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.

[0259] (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.

[0260] 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].

[0261] By using the techniques described herein in combination with methods well known in the art, the compounds shown in the table below can be prepared.

[0262]

[0263]

[0264]

[0265]

[0266] U is represented by the following general formula (22): General formula (22):

[0267]

[0268]

[0269]

[0270]

[0271]

[0272]

[0273]

[0274]

[0275]

[0276]

[0277]

[0278]

[0279]

[0280]

[0281]

[0282]

[0283]

[0284]

[0285]

[0286]

[0287]

[0288]

[0289]

[0290]

[0291]

[0292]

[0293]

[0294]

[0295]

[0296]

[0297]

[0298]

[0299]

[0300]

[0301]

[0302]

[0303]

[0304]

[0305]

[0306]

[0307]

[0308]

[0309]

[0310]

[0311]

[0312]

[0313]

[0314]

[0315]

[0316]

[0317]

[0318]

[0319]

[0320]

[0321]

[0322]

[0323]

[0324]

[0325]

[0326]

[0327]

[0328]

[0329]

[0330]

[0331]

[0332]

[0333] U is the same as in the general formula (22). In the table, Het-1 to Het-58 are each represented by the following structures.

[0334]

[0335]

[0336]

[0337]

[0338]

[0339]

[0340]

[0341]

[0342]

[0343]

[0344]

[0345]

[0346]

[0347]

[0348]

[0349]

[0350]

[0351]

[0352]

[0353]

[0354]

[0355]

[0356]

[0357]

[0358]

[0359]

[0360]

[0361]

[0362] More specifically,

[0363]

[0364] U is represented by the following general formula (23): General formula (23):

[0365]

[0366]

[0367]

[0368]

[0369]

[0370]

[0371]

[0372]

[0373]

[0374]

[0375]

[0376]

[0377]

[0378]

[0379]

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

[0430]

[0431]

[0432]

[0433]

[0434]

[0435]

[0436]

[0437]

[0438]

[0439]

[0440]

[0441]

[0442] The herbicide and pesticide composition of the present invention are characterized by containing, as an active ingredient, a compound represented by formula [1] of the present invention or an agriculturally acceptable salt thereof. The present invention also relates to a pesticide composition, more specifically a herbicidal composition, comprising one or more compounds represented by formula [1] of the present invention or agriculturally acceptable salts thereof and a carrier acceptable for agricultural chemical formulations. The compound represented by formula [1] of the present invention or the herbicidal composition of the present invention can be used in upland fields, paddy fields, or orchards by foliar application, soil application, or water surface application. The herbicide of the present invention can also be used to control common weeds in fallow fields, ridges, farm roads, waterways, cultivated pastures, cemeteries, parks, roads, playgrounds, vacant lots around buildings, cultivated land, railroad tracks, forests, etc. That is, the present invention also relates to a method of using the compound represented by formula [1] of the present invention or the herbicidal composition of the present invention to control weeds in useful plants and useful crops. The compound represented by the formula [1] according to the present invention and the herbicidal composition according to the present invention have extremely strong herbicidal properties.

[0443] Examples of weeds that can be treated with the compound represented by formula [1] according to the present invention or the herbicidal composition according to the present invention are listed below, but the present invention is not necessarily limited to these.

[0444] 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.

[0445] Furthermore, the compounds represented by formula [1] according to the present invention or the herbicidal compositions according to the present invention are 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 turfgrass. 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, diseases, etc., as well as plants that have been bred or selected to be resistant to herbicides, pests, diseases, etc. Examples of genetically modified plants are given below, but are not necessarily limited to these.

[0446] 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.

[0447] 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.

[0448] 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.

[0449] 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.

[0450] 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.

[0451] 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.

[0452] To control weeds, the herbicidal composition of the present invention can be used by adjusting the application amount of the compound represented by formula [1] according to the present invention so that it is effective against weeds but not toxic to useful plants and useful crops. Here, the effective amount 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.

[0453] The compound represented by formula [1] according to the present invention or the herbicidal composition according to 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 for sowing seeds, rice paddies, hydroponic water, and cultivation materials, by spraying, dusting, dusting, spraying, diffusing, dipping, irrigating, injecting, watering (dipping), foaming, applying, dusting, coating, spraying, fumigating, smoking, misting, painting, etc. 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 compound represented by formula [1] according to the present invention or the herbicidal composition according to the present invention is applied to control weeds, the treatment can be carried out before and throughout the growth period of useful plants and useful crops, regardless of whether weeds emerge or not. Here, a part of a plant means all parts constituting a plant, such as leaves, stems, trunks, branches, flowers, fruiting bodies, fruits, seeds, roots, tubers and rhizomes, or a combination thereof.

[0454] 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.

[0455] The additive components will now be described.

[0456] 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.

[0457] Examples of liquid carriers include monohydric alcohols such as methanol, ethanol, propanol, i-propanol, and butanol; polyhydric alcohols such as ethylene glycol, diethylene glycol, propylene glycol, hexylene glycol, polyethylene glycol, and polypropylene glycol 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.

[0458] 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.

[0459] 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.

[0460] 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.

[0461] 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.

[0462] 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.

[0463] 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.

[0464] 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.

[0465] Examples of plant debris include sawdust, coconut husks, corn cobs, tobacco stalks, and the like.

[0466] When the fungicide and pesticide compositions of the present invention contain the above-mentioned additive components, 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.

[0467] 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.

[0468] Such an embodiment can be obtained by a conventional method of mixing at least one compound of the present invention with a suitable solid or liquid carrier, and, if desired, with a suitable adjuvant (e.g., surfactant, solvent, stabilizer) for improving the dispersibility of the active ingredient or other properties. When used, the compound is diluted to a suitable concentration and sprayed or applied directly.

[0469] The herbicidal composition of the present invention may contain one or more compounds represented by the formula [1] or salts thereof according to the present invention.

[0470] The blending ratio of the compound represented by formula [1] according to the present invention in the herbicidal composition of the present invention is appropriately selected as needed, but in the case of dusts and granules, it is appropriately selected from the range of 0.001 to 50% (by weight), preferably 0.005 to 30% (by weight). In the case of emulsifiable concentrates and wettable powders, it is appropriately selected from the range of 1 to 50% (by weight), preferably 5 to 30% (by weight). In the case of flowables, it is appropriately selected from the range of 1 to 50% (by weight), preferably 2 to 30% (by weight).

[0471] 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.

[0472] 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.

[0473] 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)

[0474] 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).

[0475] 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%).

[0476] 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%).

[0477] 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).

[0478] Example 2 Preparation of N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-chloro-1,3-dihydroisoindol-1-one (Compound 2-3)

[0479] 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).

[0480] 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%).

[0481] 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). ＴＭThe 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).

[0482] Example 3 Preparation of N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5-chloro-8-fluoro-3,4-dihydroisoquinolin-1(2H)-one (Compound 3-64)

[0483] 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).

[0484] 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).

[0485] Example 4 Preparation of N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinolin-1(2H)-one (Compound 3-149)

[0486] 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).

[0487] 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).

[0488] 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%).

[0489] 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).

[0490] 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%).

[0491] 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).

[0492] 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). ＴＭThe 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).

[0493] Example 5 Preparation of N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-8-fluoro-5-methyl-3,4-dihydroisoquinolin-1(2H)-one (Compound 3-151)

[0494] 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).

[0495] 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).

[0496] 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).

[0497] 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).

[0498] Example 6 Preparation of N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-8-fluoro-5-trifluoromethyl-3,4-dihydroisoquinolin-1(2H)-one (Compound 3-152)

[0499] 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%).

[0500] 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 column (eluted with ethyl acetate-hexane: 5%-20%) to give the title compound as a yellow oil (1.17 g, 65% yield).

[0501] 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).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 (918 mg, 89% yield).

[0502] 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).

[0503] 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).

[0504] Example 7 Preparation of N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-8-fluoro-5-methoxy-3,4-dihydroisoquinolin-1(2H)-one (Compound 3-153)

[0505] 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%).

[0506] 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 column (eluted with ethyl acetate-hexane: 5%-20%) to give the title compound as a brown oil (1.65 g, 67% yield).

[0507] 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).

[0508] 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).

[0509] 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).

[0510] Example 8 Preparation of N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-8-chloro-5-fluoro-3,4-dihydroisoquinolin-1(2H)-one (Compound 3-154)

[0511] 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).

[0512] 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).

[0513] 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).

[0514] 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)

[0515] 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%).

[0516] 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).

[0517] 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)

[0518] 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%).

[0519] 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).

[0520] 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).

[0521] 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).

[0522] 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)

[0523] 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 column chromatography column (eluted with ethyl acetate-hexane: 15%-50%) to give the title compound as a colorless resinous solid (171 mg, 21% yield).

[0524] 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).

[0525] Example 13 Preparation of N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-9-chloro-2,3,4,5-tetrahydro-1H-2-benzazepin-1-one (Compound 5-2)

[0526] 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).

[0527] 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%).

[0528] 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).

[0529] Example 14 Preparation of N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-4,5-dihydro-6H-thieno[2,3-c]pyrrol-6-one (Compound 6-1)

[0530] 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).

[0531] 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 column (eluted with chloroform-methanol: 3%-6%) to give the title compound as a pale yellow resinous solid (450 mg, 40% yield).

[0532] 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).

[0533] Example 15 Preparation of N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5,6-dihydrofurano[2,3-c]pyrimidin-7(4H)-one (Compound 6-4)

[0534] 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%) to give the title compound as a colorless oil (716 mg, 40% yield).

[0535] Step 2: Preparation of 5,6-dihydrofurano[2,3-c]pyrimidin-7(4H)-one The compound obtained in Step 1 of Example 15 above (236 mg) was dissolved in dichloromethane (4 mL), and trifluoromethanesulfonic acid (1.23 g) 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 anhydrous sodium sulfate, and inorganic substances were filtered off. The solvent was then 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: 15%-80%) to give the title compound as a pale yellow resinous solid (29 mg, 26% yield).

[0536] Step 3: Preparation of N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5,6-dihydrofurano[2,3-c]pyrimidin-7(4H)-one The compound obtained in Step 2 of Example 15 (19 mg), 1,1,1-trifluoro-N-[2-(hydroxymethyl)phenyl]methanesulfonamide (37 mg) (a compound described in WO 2010 / 026989 ), and paratoluenesulfonic acid monohydrate (3 mg) were dissolved in orthodichlorobenzene (1 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 (21 mg, 41% yield).

[0537] Example 16 Preparation of N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-5,6-dihydrothieno[2,3-c]pyridin-7(4H)-one (Compound 6-22)

[0538] Step 1: Preparation of N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5,6-dihydrothieno[2,3-c]pyridin-7(4H)-one 5,6-Dihydrothieno[2,3-c]pyridin-7(4H)-one (91 mg) (a compound described in WO 2007 / 146759), 1,1,1-trifluoro-N-[2-(hydroxymethyl)phenyl]methanesulfonamide (127 mg) (a compound described in WO 2010 / 026989), and paratoluenesulfonic acid monohydrate (54 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: 15%-50%) to give the title compound as a colorless resinous solid (90 mg, 40% yield).

[0539] 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 16 above (90 mg), ethyl chloroformate (63 mg), and sodium bicarbonate (48 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 HPLC system (eluted with ethyl acetate-hexane: 5%-30%) to give the title compound as a yellow oil (103 mg, 96% yield).

[0540] Example 17 Preparation of N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-thione (Compound 7-2) The compound obtained in Step 6 of Example 4 (390 mg) and Lawesson's reagent (2.6 g) were dissolved in toluene (9.5 mL) and stirred under reflux for 4 days. The reaction mixture was concentrated, and the residue was purified by flash filtration using an automatic purification system (Biotage AB / Isolera). ＴＭ The residue was purified by silica gel flash chromatography on a 100% hexane column (eluted with chloroform-hexane: 20%-100%) to give the title compound as a yellow resinous solid (129 mg, 32% yield).

[0541] Example 18 Preparation of N-[2-(N-ethoxycarbonyl-N-trifluoromethylsulfonyl)aminobenzyl]-4-methyl-3,4-dihydroisoquinolin-1(2H)-one (Compound 7-15)

[0542] Step 1: Preparation of 2-(2,5-difluorophenyl)propanenitrile 2,5-Difluorophenylacetonitrile (2 g) and iodomethane (1.85 g) were dissolved in tetrahydrofuran (30 mL), and a solution of potassium tert-butoxide (2.2 g) in tetrahydrofuran (10 mL) was added dropwise at -78°C. The mixture was gradually warmed to room temperature and then stirred at room temperature overnight. A saturated aqueous solution of ammonium chloride was added to the reaction mixture, 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 apparatus (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 yellow oil (1.76 g, 81% yield).

[0543] Step 2: Preparation of 2-(2,5-difluorophenyl)propan-1-amine The compound obtained in Step 1 of Example 18 above (1.76 g) was dissolved in tetrahydrofuran (20 mL), and dimethylsulfide borane (5 mL) was added, followed by heating under reflux for 8 hours. 1 N aqueous hydrochloric acid solution was added dropwise to the reaction solution, and the mixture was heated under reflux for 2 hours. Water was added to the reaction solution, and the mixture was washed with dichloromethane. Sodium hydroxide was added to the aqueous layer to make the solution basic, followed by extraction 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 oil (1.37 g, yield 76%).

[0544] Step 3: Preparation of methyl 2-[[[2-(2,5-difluorophenyl)propyl]carbamoyl]oxy]benzoate The compound obtained in Step 1 of Example 4 (2.4 g) and the compound obtained in Step 2 of Example 18 (1.37 g) were dissolved in tetrahydrofuran (25 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%) to give the title compound as a colorless oil (2.27 g, 89% yield).

[0545] Step 4: Preparation of 4-methyl-3,4-dihydroisoquinolin-1(2H)-one The compound obtained in Step 3 of Example 18 above (2.27 g) was dissolved in dichloromethane (33 mL), and trifluoromethanesulfonic acid (9.76 g) was added dropwise in an ice-water bath, followed by stirring at room temperature for 3 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 anhydrous sodium sulfate, and the inorganic matter was filtered off. The solvent was then 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 HPLC system (eluted with ethyl acetate-hexane: 20%-80%) to give the title compound as a colorless oil (1.07 g, 83% yield).

[0546] Step 5: Preparation of N-[2-(N-trifluoromethylsulfonyl)aminobenzyl]-4-methyl-3,4-dihydroisoquinolin-1(2H)-one The compound obtained in Step 4 of Example 18 above (360 mg), 1,1,1-trifluoro-N-[2-(hydroxymethyl)phenyl]methanesulfonamide (411 mg) (a compound described in WO 2010 / 026989 ), 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). 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 (636 mg, 80% yield).

[0547] Step 6: Preparation of N-[2-(N-ethoxycarbonyl-N-trifluoromethylsulfonyl)aminobenzyl]-4-methyl-3,4-dihydroisoquinolin-1(2H)-one The compound obtained in Step 5 of Example 18 above (456 mg), ethyl chloroformate (285 mg), and sodium bicarbonate (221 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 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 (472 mg, 89% yield).

[0548] Example 19: Preparation of N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-1,3-dihydroindol-2-one (Compound 8-7)

[0549] Step 1: Preparation of N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-1,3-dihydroindol-2-one Oxiindoline (250 mg), 1,1,1-trifluoro-N-[2-(hydroxymethyl)phenyl]methanesulfonamide (140 mg) (a compound described in WO 2010 / 026989 ), and paratoluenesulfonic acid monohydrate (95 mg) were dissolved in orthodichlorobenzene (3 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 100% column (eluted with ethyl acetate-hexane: 10%-40%) to give the title compound as a colorless resinous solid (87 mg, 23% yield).

[0550] Step 2: Preparation of N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-1,3-dihydroindol-2-one The compound obtained in Step 1 of Example 19 above (76 mg), ethyl chloroformate (56 mg), and sodium bicarbonate (44 mg) were dissolved in acetonitrile (10 mL) and heated under reflux for 3 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: 10%-50%) to give the title compound as a yellow oil (75 mg, 80% yield).

[0551] Example 20: Preparation of N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-1,4-dihydroisoquinolin-3(2H)-one (Compound 9-5)

[0552] Step 1: Preparation of N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-1,4-dihydroisoquinolin-3(2H)-one 1,4-Dihydroisoquinolin-3(2H)-one (570 mg) (a compound described in WO 2003 / 082265), 1,1,1-trifluoro-N-[2-(hydroxymethyl)phenyl]methanesulfonamide (824 mg) (a compound described in WO 2010 / 026989), and paratoluenesulfonic acid monohydrate (307 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%-80%) to give the title compound as a colorless resinous solid (700 mg, 57% yield).

[0553] Step 2: Preparation of N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-1,4-dihydroisoquinolin-3(2H)-one The compound obtained in Step 1 of Example 20 above (673 mg), ethyl chloroformate (285 mg), and sodium bicarbonate (221 mg) were dissolved in acetonitrile (30 mL) and heated under reflux for 4 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 (Isolera, manufactured by Biotage AB). ＴＭ The residue was purified by silica gel flash chromatography on a 100-well plate (eluted with ethyl acetate-hexane: 10%-30%) to give the title compound as a yellow oil (623 mg, yield 78%). The compounds shown in Table 159 to Table 187 were synthesized using a similar procedure.

[0554] In addition, as in No. 3-88, X １ and X ２ together represent -S-CH=N-, S is X１ and N is bonded to the bonding point of X ２ Also, as in No. 7-11, E １ and E ２ When these are taken together to represent -CH=C(OMe)-, CH is E １ and C(OMe) is bonded to the bonding point of E ２ It binds to the attachment point of

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[0584] The compounds obtained in the above examples and the compounds of the present invention prepared in the same manner １ H-NMR data (CDCl ３ / TMS δ (ppm) values) are shown in the table below. Note that some of the compounds of the present invention are diastereomeric mixtures, and rotational isomers are observed in NMR. In the table below, "lp" means a low-polarity compound among the diastereomeric mixtures. "mp" means a high-polarity compound among the diastereomeric mixtures. "trans" means that the data is for the trans isomer, which is the major component of the geometric isomer mixture. "DMSO-d6" means that dimethyl sulfoxide-d6 was used as the measurement solvent. "CD3OD" means that methanol (d4) was used as the measurement solvent.

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[0615] Next, examples of the use of the present invention will be described. (1) Formulation

[0616] Formulation Example 1: Wettable powder 10 parts of the compound of the present invention, 15 parts of sodium lignosulfonate, 2 parts of sodium lauryl sulfate, 15 parts of hydrous silicon dioxide and 58 parts of clay were mixed and pulverized to obtain a 10% wettable powder.

[0617] Formulation Example 2: Flowable formulation 10 parts of the compound of the present invention, 4 parts of polyoxyethylene allylphenyl ether sulfate, 5 parts of polyoxyethylene alkyl ether, 5 parts of propylene glycol, 0.2 parts of a silicone antifoaming agent, 0.8 parts of sodium montmorillonite, and 50 parts of water were mixed and wet-pulverized using a Dynomill to obtain a pulverized suspension. To 75 parts of the pulverized suspension, 10 parts of a xanthan gum solution containing 0.2 parts and 0.1 parts of xanthan gum and 2-benzisothiazolin-3-one, respectively, and 15 parts of water were added, and the mixture was mixed to obtain a 10% aqueous suspension pesticide composition.

[0618] Formulation Example 3 Emulsion 10 parts of the compound of the present invention, 2 parts of calcium dodecylbenzenesulfonate, and 15 parts of castor oil ethoxylate were mixed and dissolved in 73 parts of an aromatic hydrocarbon mixture to obtain a homogeneous 10% emulsifiable oily liquid.

[0619] <Formulation Example 4> Water dispersible granules 10 parts of the present invention compound, 20 parts of sodium ligninsulfonate, 10 parts of the sodium salt of naphthalenesulfonic acid condensate, 3 parts of sodium alkylbenzenesulfonate, 0.5 parts of silicon-based defoamer, 5 parts of diatomaceous earth, 10 parts of ammonium sulfate, 10 parts of talc, 31.5 parts of clay are added, thoroughly stirred and mixed, and pulverized to obtain pulverized material.Appropriate amount of water is added to the pulverized material as required, and granulated with a granulator, dried and then sieved to obtain 10% hydration fine granules.

[0620] Formulation Example 5: Emulsion 10 parts of the compound of the present invention, 15 parts of an aromatic hydrocarbon mixture, 2 parts of calcium dodecylbenzenesulfonate, 20 parts of polyoxyethylene castor oil, and 4 parts of propylene glycol were dissolved to obtain a mixed solution, which was then added to 49 parts of water and mixed using a homogenizer to obtain a homogeneous 10% emulsion.

[0621] Formulation Example 6 Granules 10 parts of the compound of the present invention, 3 parts of a polycarboxylic acid type anionic surfactant, 0.2 parts of dioctyl sodium sulfosuccinate, 2 parts of dextrin, 15 parts of sodium bentonite, and 69.8 parts of calcium carbonate were mixed and uniformly mixed, and then an appropriate amount of water was added and kneaded, and the mixture was extruded in a basket granulator to form granules, dried, and sieved to obtain 10% fine granules.

[0622] Formulation Example 7 Microemulsion 10 parts of the compound of the present invention, 12 parts of fatty acid dimethylamide, 10 parts of cyclohexanone, and 15 parts of arylphenol ethoxylate were mixed, and 10 parts of alcohol ethoxylate and 43 parts of water were added thereto, followed by stirring under heating for several minutes to obtain a stable 10% water-soluble liquid.

[0623] (2) Test to evaluate herbicidal effect by flooding treatment in paddy fields <Test Example 1> Test to evaluate herbicidal effect by flooding treatment in paddy fields 40 cm ２ Plastic cups were filled with puddled paddy field soil, and seeds of Echinochloa oryzicola (EC), Scirpus juncoides (SJ), Monochoria vaginalis (MV), and Lythrum gracilis (AM) were sown and grown in a greenhouse. After growing the plants for 14 days, the plants were flooded with water to a depth of 3 cm, and a 10% wettable powder prepared according to Formulation Example 1 was diluted with distilled water and applied dropwise to the water surface. The application rates were 1000, 500, 250, 125, 63, 31, or 16 g of active ingredient per hectare. The test was conducted in duplicate. 21 days after treatment, the herbicidal effect (above-ground growth inhibition rate (%): 100 (complete death) to 0 (no effect)) was investigated. The results of the present invention are shown below.

[0624] Effect on barnyardgrass Compounds 3-188 and 6-17 showed herbicidal activity of 80% or more at a dose of 31 g a.i. / ha. Compound 6-24 showed herbicidal activity of 80% or more at a dose of 63 g a.i. / ha. Compounds 3-69, 3-99, 3-103, 3-109, 3-130, 3-149, 3-164, 3-175, 3-186, 3-189, 3-193, 3-199, 3-218, 3-229, 3-241, 3-243, 3-246, 3-247, 3-255, 4-16, 4-26, and 4-30 showed herbicidal activity of 80% or more at a dose of 125 g a.i. / ha.

[0625] Compounds 2-55, 3-9, 3-10, 3-42, 3-58, 3-63, 3-64, 3-97, 3-98, 3-100, 3-101, 3-112, 3 -113, 3-117, 3-129, 3-133, 3-140, 3-154, 3-173, 3-177, 3-179, 3-181, 3-182, 3- 183, 3-190, 3-192, 3-198, 3-202, 3-205, 3-207, 3-214, 3-215, 3-217, 3-219, 3-222, 3-223, 3-227, 3-228, 3-234, 3-238, 3-244, 5-6, 6-4, 6-22, 8-1, and 9-1 showed herbicidal effects of 80% or more when treated at a dose of 250 g a.i. / ha.

[0626] Compounds 2-1, 2-2, 2-22, 2-32, 3-2, 3-3, 3-19, 3-23, 3-27, 3-39, 3-41, 3-53, 3-66, 3-73, 3-80, 3-104, 3-107, 3-108, 3-111, 3-115, 3-121, 3 -124, 3-125, 3-127, 3-131, 3-132, 3-134, 3-135, 3-136, 3-139, 3-146, 3-148, 3-151, 3-160, 3-163, 3-165, 3-167, 3-171, 3-172, 3-17 4, 3-178, 3-180, 3-184, 3-185, 3-187, 3-203, 3-204, 3-206, 3-208, 3-211, 3-212, 3-220, 3-221, 3-224, 3-226, 3-232, 3-233, 3-235, 3-237, 3-239, 3-240, 3-249, 3-252, 3-254, 4-2, 4-5, 4-6, 4-7, 4-36, 5-1, 5-2, 6-7, 6-8, 6-12, 6-16, 6-20, 6-23, 6-26, 7-9, and 8-7 showed herbicidal effects of 80% or more when treated with a dose of 500 g a.i. / ha. Compound 8-2 showed a herbicidal effect of 80% or more when treated at a dose of 1000 g a.i. / ha.

[0627] Effect on Scirpus juncoides Compound 3-116 showed a herbicidal effect of 80% or more when treated at a dose of 16 g ai / ha. Compounds 3-124, 3-175, 3-202, 3-226, 3-255, 6-4, 6-8, and 6-12 showed a herbicidal effect of 80% or more when treated at a dose of 31 g ai / ha.

[0628] Compounds 1-2, 1-6, 2-9, 2-55, 3-3, 3-4, 3-28, 3-39, 3-41, 3-63, 3-69, 3-107, 3-11 1, 3-112, 3-121, 3-126, 3-129, 3-130, 3-141, 3-146, 3-149, 3-173, 3-179, 3- 184, 3-185, 3-189, 3-204, 3-205, 3-206, 3-207, 3-208, 3-217, 3-227, 3-229, 3-241, 3-246, 3-247, 3-254, 6-14, 6-16, 6-17, 6-22, 7-1, 7-7, and 7-8 showed herbicidal effects of 80% or more when treated at a dose of 63 g a.i. / ha.

[0629] Compounds 1-1, 1-5, 1-9, 2-1, 2-3, 2-41, 3-12, 3-22, 3-30, 3-37, 3-42, 3-44, 3-48, 3-58, 3-59, 3 -64, 3-70, 3-73, 3-77, 3-88, 3-94, 3-98, 3-101, 3-135, 3-142, 3-145, 3-147, 3-148, 3-15 4, 3-157, 3-164, 3-166, 3-181, 3-182, 3-199, 3-210, 3-218, 3-219, 3-220, 3-223, 3-238, 3-249, 4-1, 4-7, 4-29, 4-30, 4-40, 6-1, 6-21, 6-24, 7-9, 7-10, 7-15, 7-16, and 9-1 showed herbicidal effects of 80% or more when treated at a dose of 125 g a.i. / ha.

[0630] Compounds 1-4, 2-4, 2-5, 2-22, 2-34, 2-40, 3-1, 3-2, 3-6, 3-7, 3-9, 3-10, 3-15, 3-16, 3-17, 3-18, 3-19, 3-21, 3-25, 3 -33, 3-36, 3-45, 3-46, 3-52, 3-62, 3-65, 3-66, 3-67, 3-92, 3-106, 3-110, 3-117, 3-131, 3-136, 3-138, 3-168, 3-170, 3-190, 3-192, 3-193, 3-209, 3-212, 3-214, 3-237, 3-242, 3-243, 3-251, 3-252, 4-2, 4-5, 4-6, 4-10, 4-13, 4-14, 4-15, 4-16, 4-26, 4-27, 4-28, 4-32, 4-36, 4-37, 4-38, 4-41, 4-42, 5-1, 6-2, 6-5, 7-3, and 8-1 showed herbicidal effects of 80% or more when treated at a dose of 250 g a.i. / ha.

[0631] Compounds 1-3, 1-10, 1-11, 2-7, 2-18, 2-32, 2-33, 2-37, 2-57, 3-14, 3-23, 3-27, 3-38, 3-43, 3-53, 3-61, 3-68, 3-76, 3-78 , 3-89, 3-90, 3-91, 3-96, 3-100, 3-102, 3-103, 3-104, 3-105, 3-108, 3-119, 3-122, 3-128, 3-137, 3-139, 3-152, 3- Compounds 153, 3-156, 3-158, 3-159, 3-163, 3-165, 3-167, 3-174, 3-177, 3-178, 3-183, 3-197, 3-198, 3-222, 3-228, 3-230, 3-233, 3-239, 3-244, 3-253, 4-3, 4-8, 4-9, 4-11, 4-12, 4-21, 5-2, 5-6, 6-6, 6-13, 6-15, 6-18, 8-2, 9-2, and 9-5 showed herbicidal activity of 80% or more when treated with a dose of 500 g a.i. / ha. Compounds 7-17, 8-5, and 9-6 showed herbicidal activity of 80% or more when treated with a dose of 1000 g a.i. / ha. A treatment of 1 / ha showed a herbicidal effect of 80% or more.

[0632] Effect on Monochoria vaginalis Compounds 3-149, 3-202, 3-211, 3-220, 3-222, and 3-232 showed herbicidal activity of 80% or more when treated at a dose of 16 g a.i. / ha. Compounds 2-22, 3-63, 3-69, 3-101, 3-107, 3-109, 3-112, 3-135, 3-136, 3-166, 3-198, 3-227, 3-234, 3-246, 3-247, 4-26, 4-30, and 4-36 showed herbicidal activity of 80% or more when treated at a dose of 31 g a.i. / ha.

[0633] Compounds are 2-1, 2-55, 3-2, 3-6, 3-19, 3-44, 3-59, 3-76, 3078, 3-97, 3-99, 3-100, 3-102, 3-103, 3-111, 3-113, 3-116, 3-117, 3-121, 3-125, 3-128, 3-129, 3-131, 3-133, 3-137, 3-145, 3-154, 3-156, 3-165, 3-173, 3-174, 3-175, 3-177, 3-178, 3-179, 3-180, 3-181, 3-182, 3-183, 3-184, 3-188, 3-190, 3-197, 3-199, 3-203, 3-204, 3-206, 3-215, 3-217, 3-219, 3-225, 3-230, 3-233, 3-235, 3-237, 3-240, 3-241, 3-242, 3-249, 3-252, 3-254, 4-8, 4-15, 4-16, 4-22, 4-29, 4-37, 5-6, 6-4, 6-5, 6-7, 7-1, 7-7, 7-9, and 7-10 showed herbicidal effects of 80% or more when treated with a dose of 63 g a.i. / ha.

[0634] Compounds 1-6, 2-18, 2-31, 2-34, 2-41, 3-1, 3-3, 3-12, 3-21, 3-23, 3-28, 3-36, 3-37, 3-39, 3-41, 3-42, 3-43, 3-46, 3-55, 3-58, 3-60, 3 -62, 3-64, 3-66, 3-70, 3-71, 3-73, 3-98, 3-104, 3-105, 3-106, 3-108, 3-115, 3-118, 3-124, 3-130, 3-140, 3-157, 3-171, 3-185, 3 3-186, 3-187, 3-189, 3-191, 3-192, 3-193, 3-195, 3-201, 3-207, 3-208, 3-218, 3-228, 3-229, 3-238, 3-243, 3-255, 4-7, 4-12, 4-14, 4-21, 4-31, 4-38, 4-40, 4-41, 4-42, 5-1, 5-3, 5-5, 6-1, 6-6, 6-8, 6-13, 6-15, 6-16, 6-17, 7-2, 7-12, 7-13, 7-15, and 8-1 showed herbicidal effects of 80% or more when treated with a dose of 125 g a.i. / ha.

[0635] Compounds 1-1, 1-3, 1-4, 2-2, 2-3, 2-32, 2-37, 2-40, 2-57, 3-9, 3-13, 3-15, 3-20, 3-22, 3-24, 3-25, 3-27, 3-30, 3 -33, 3-35, 3-45, 3-51, 3-52, 3-53, 3-57, 3-61, 3-72, 3-77, 3-91, 3-110, 3-114, 3-119, 3-126, 3-127, 3-134 , 3-139, 3-148, 3-151, 3-153, 3-163, 3-169, 3-170, 3-209, 3-210, 3-212, 3-221, 3-223, 3-244, 4-2, 4-5, 4-6, 4-11, 4-13, 4-17, 4-18, 4-23, 4-27, 5-2, 6-14, 6-19, 6-20, 6-22, 7-8, 7-16, 8-2, 8-7, 8-8, and 9-1 showed herbicidal effects of 80% or more when treated with a dose of 250 g a.i. / ha.

[0636] Compounds 1-2, 1-5, 1-9, 2-4, 2-5, 2-7, 2-9, 2-23, 2-26, 2-30, 2-33, 2-36, 2-38, 2-43, 2-47, 2-51, 3-4, 3-1 1, 3-14, 3-16, 3-38, 3-65, 3-74, 3-80, 3-84, 3-87, 3-88, 3-89, 3-92, 3-94, 3-96, 3-120, 3-122, 3-12 Compounds 3, 3-143, 3-147, 3-150, 3-158, 3-159, 3-160, 3-161, 3-167, 3-172, 3-214, 3-224, 3-226, 3-239, 4-1, 4-3, 4-4, 4-9, 4-10, 5-4, 6-10, 6-12, 6-18, 6-21, 6-25, 6-26, 7-3, 8-3, 8-5, 8-9, 8-11, and 9-5 showed herbicidal activity of 80% or more at a dose of 500 g a.i. / ha. Compounds 8-4 and 9-3 showed herbicidal activity of 80% or more at a dose of 1000 g a.i. / ha.

[0637] Effect on Lythrum salicaria Compounds 1-6, 2-18, 3-2, 3-3, 3-4, 3-24, 3-25, 3-42, 3-57, 3-63, 3-64, 3-69, 3-70, 3-72, 3-91, 3-96, 3-97, 3-98, 3-99, 3-100, 3-101, 3-102, 3-103, 3-104, 3-105, 3-107, 3-108, 1-109, 1-110, 3-111, 3-112, 3-113, 3-114, 3-115, 3-116, 3-11 7, 3-119, 3-121, 3-124, 3-126, 3-127, 3-128, 3-129, 3-130, 3-131, 3-132, 3-133, 3-134, 3-135, 3-136, 3-137, 3-140, 3-149, 3-154, 3-164, 3-166, 3-170, 3-171, 3-172, 3-173, 3-174, 3-175, 3-177, 3-178, 3-179, 3-180, 3-181, 3-182, 3-183, 3-184, 3-185, 3-186, 3-188, 3-189, 3-190, 3-192, 3-193, 3-195, 3-197, 3-198, 3-201, 3-202, 3-203, 3-204, 3-205, 3-206, 3-207, 3-208, 3-210, 3-211, 3-212, 3-214, 3-215, 3-217, 3-218, 3-219, 3-220, 3-221, 3-222, 3-223, 3- 225, 3-226, 3-227, 3-228, 3-229, 3-232, 3-233, 3-234, 3-237, 3-240, 3-241, 3-242, 3-243, 3-244, 3-246, 3-247, 3-249, 3-252, 3-254, 3-255, 4-12, 4-15, 4-16, 4-21, 4-26, 4-30, 4-36, 6-4, 6-8, 6-17, 6-18, 6-22, 7-2, 7-9, and 7-15 showed herbicidal effects of 80% or more when treated at a dose of 16 g a.i. / ha.

[0638] Compounds 1-5, 2-9, 2-22, 3-1, 3-10, 3-26, 3-33, 3-44, 3-46, 3-48, 3-51, 3-53, 3-58, 3-59, 3-60, 3-61, 3-76, 3-78, 3-118, 3-125, 3-142, 3-146, 3-148, 3-156, 3-199, 3-209, 3-224, 3-230, 3-235, 3-239, 4-13, 4-22, 4-27, 4-29, 4-37, 4-41, 6-7, 6-12, 6-14, 6-16, and 7-10 showed herbicidal activity of 80% or more when treated at a dose of 31 g a.i. / ha.

[0639] Compounds 1-2, 2-3, 2-4, 2-19, 2-55, 3-6, 3-7, 3-15, 3-19, 3-10, 3-21, 3-23, 3-30, 3-31, 3-34, 3-36, 3-39, 3-40, 3-41, 3-43, 3-47, 3-49, 3-50...

Claims

1. General formula [1] 【Chemistry 1】 {In the formula, A is an optionally substituted benzene ring or heteroaromatic ring, E is -C(R ５ ) (Caution ６ ) - oxygen atom, sulfur atom, SO, SO ２ , or N(R ７ ) and W is an oxygen atom or a sulfur atom, o is between 0 and 4. p is between 0 and 4. m is between 0 and 3. n is between 0 and 3. R １ Hello C １ ~C ６ It is alkyl, R ２ is C substituted by one or more substituents selected from hydrogen atoms, Z １ to C １ alkyl, C ６ to C ２ alkenyl, halo C ６ to C ２ alkenyl, C ６ to C ２ alkynyl, halo C ６ to C[[ID=2l]] ２ alkynyl, (C ６ to C １ alkyl)carbonyl, (halo C １２ to C １ alkyl)carbonyl, (C １２ to C ３ cycloalkyl)carbonyl, (halo C ６ to C ３ cycloalkyl)carbonyl, (C ６ to C １ alkyl C ６ to C ３ cycloalkyl)carbonyl, C ６ to C １ alkyl(halo C ６ to C ３ cycloalkyl)carbonyl, (C ６ to C ３ U cycloalkoxy)carbonyl, (C ６ to C ２ alkenyl)carbonyl, (halo C ６ to C ２ alkenyl)carbonyl, Z ６ phenyl(C<b000042>substituted by one or more substituents selected from Z ２ to C ６ alkenyl)carbonyl, C １ to C ６ alkoxy(C ２ to C ６ alkenyl)carbonyl, (C ２ to C ６ alkynyl)carbonyl, Z ２ phenylcarbonyl substituted by one or more substituents selected from Z ２ heterocyclylcarbonyl optionally substituted by one or more substituents selected from, C ３ -C ６ cycloalkyl(C １ -C ６ alkyl)carbonyl, Z ４ (C １ -C ６ alkyl)carbonyl substituted by one substituent selected from, (hydroxyC 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 substituted by one substituent selected from, phenoxy(haloC １ -C ６ alkyl)carbonyl, Z ５ (haloC １ -C ６ alkyl)carbonyl substituted by, tri(C １ -C ６ alkyl)silyloxy(C １ -C ６ alkyl)carbonyl, C １ -C ６ alkoxyC １ -C ６ alkoxy(C １ -C ６ alkyl)carbonyl, (C<00000​​​​​​​​​​​​​​​​​​​​​ ６ Alkyl)carbonyl, C １ ~C ６ Alkylthio(C １ ~C ６ Alkyl)carbonyl, Halo C １ ~C ６ Alkylthio(C １ ~C ６ (Alkyl)carbonyl, (C １ ~C １２ Alkoxy)carbonyl, (halo C １ ~C ６ Alkoxy) carbonyl, (C ３ ~C ６ Cycloalkyloxy)carbonyl, (C ２ ~C ６ Alkenyloxy)carbonyl, (halo C ２ ~C ６ Alkenyloxy)carbonyl, (C ２ ~C ６ Alkynyloxy)carbonyl, Z ２ A phenoxycarbonyl, Z which may be substituted with one or more substituents selected from ２ A heterocyclyloxycarbonyl, C which may be substituted with one or more substituents selected from ３ ~C ６ Cycloalkyl (C １ ~C ６ Alkoxy) carbonyl, Z ４ Substituted by one substituent selected from (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 (C) substituted with one or more substituents selected from alkoxy 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 Alkylsulfonyloxy (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, 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 Alkylsulfonyl (C １ ~C ６ Alkoxy) carbonyl, (C １ ~C ６ Alkylthio)carbonyl, (halo C １ ~C ６ Alkylthio)carbonyl, mono(C) １ ~C ６ Alkyl)aminocarbonyl, mono(halo C) １ ~C ６ Alkyl)aminocarbonyl, the same or different di(C) １ ~C ６ Alkyl)aminocarbonyl, the same or different halo(C) １ ~C ６ Alkyl)aminocarbonyl, C １ ~C ６ Alkoxyoxalyl, C １ ~C ６ Alkyl sulfonyl, Halo C １ ~C ６ Alkyl sulfonyl, C ３ ~C ６ Cycloalkylsulfonyl, C ２ ~C ６ Alkenylsulfonyl, Halo C １ ~C ６ Alkenylsulfonyl, Z ２ Phenylsulfonyl, Z which may be substituted with one or more substituents selected from ２ A heterocyclylsulfonyl, which may be substituted with one or more substituents selected from C ３ ~C ６ Cycloalkyl C １ ~C ６ Alkyl sulfonyl, Z ４ C substituted with one substituent selected from １ ~C ６ Alkyl sulfonyl, C １ ~C ６ Alkoxy C １ ~C ６ Alkyl sulfonyl, amino sulfonyl, mono C １ ~C ６ Alkylaminosulfonyl, diC, which may be the same or different. １ ~C ６ Alkylaminosulfonyl, C １ ~C ６ Alkylthio, Halo C １ ~C ６ Alkylthio or cyano, Z １ These are, independently of each other, halogen atoms, C ３ ~C ６ Cycloalkyl, Z ２ Phenyl, Z which may be substituted with one or more substituents selected from ２ A heterocyclyl, cyano, or Z which may be substituted with one or more substituents selected from the above. ３ C may be substituted with one or more substituents selected from １ ~C ６ Alkoxy, C ３ ~C ６ Cycloalkyloxy, Z ２ Phenoxy, Z which may be substituted with one or more substituents selected from ２ Phenylcarbonyloxy, Z which may be substituted with one or more substituents selected from ２ A heterocyclylcarbonyloxy which may be substituted with one or more substituents selected from (C) １ ~C ６ Alkyl)carbonyloxy, (C ３ ~C ６ Cycloalkyl)carbonyloxy, (C １ ~C ６ Alkoxy) Carbonyl Oxy, Z ２ Phenoxycarbonyloxy, -CONR which may be substituted with one or more substituents selected from １１ R １２ C may be substituted with one or more halogen atoms. １ ~C ６ C may be substituted with alkylthio or one or more halogen atoms. １ ~C ６ C may be substituted with alkylsulfinyl or one or more halogen atoms. １ ~C ６ Alkyl sulfonyl, Z ２ Phenylthio, Z which may be substituted with one or more substituents selected from ２ Phenylsulfinyl, Z which may be substituted with one or more substituents selected from ４ C may be substituted with one substituent selected from the following. １ ~C ６ Alkylthio, Z ４ C may be substituted with one substituent selected from the following. １ ~C ６ Alkyl sulfinyl, Z ４ C may be substituted with one substituent selected from the following. １ ~C ６ It may be substituted with alkylsulfinyl, thiocyanate, or one or more halogen atoms (C １ ~C ６ (C)carbonyl, which may be substituted with one or more halogen atoms. １ ~C ６ Alkoxy) carbonyl, and Z ２ Selected from phenylcarbonyl which may be substituted with one or more substituents selected from, Z ２ These are, independently of each other, halogen and C １ ~C ６ Alkyl, C ２ ~C ６ Alkenil, C ２ ~C ６ Alkinyl, C ３ ~C ６ Cycloalkyl, Halo C １ ~C ６ Alkyl, Halo C ３ ~C ６ Cycloalkyl, C １ ~C ６ Alkoxy, Halo C １ ~C ６ Alkoxy, C １ ~C ６ Alkylthio, Halo C １ ~C ６ Alkylthio, C １ ~C ６ Alkyl sulfinyl, Halo C １ ~C ６ Alkyl sulfinyl, C １ ~C ６ Alkyl sulfonyl, Halo C １ ~C ６ Alkyl sulfonyl, phenyl, (C １ ~C ６ Alkyl)carbonyl, (halo C １ ~C ６ (Alkyl)carbonyl, (C １ ~C ６ Alkoxy) carbonyl, carboxyl, mono(C) １ ~C ６ Alkyl)aminocarbonyl, Z ６ Phenyl, Z substituted with one or more more selected substituents. ７ A heterocyclyl, Z which may be substituted with one or more substituents selected from the above. ７ Phenoxy, Z which may be substituted with one or more more selected substituents. ７ Phenylthio, Z which may be substituted with one or more more selected substituents. ７ Phenyl sulfinyl, Z which may be substituted with one or more more selected substituents. ７ Phenylsulfonyl, Z which may be substituted with one or more more selected substituents. ７ Phenylcarbonyl, di(C) which may be substituted with one or more substituents selected from the above. １ ~C ６ Alkyl)aminocarbonyl, -NR １３ R １４ , representing a hydroxyl group, cyano, or nitro, Or, two Z ２ The carbon atoms may combine with adjacent carbon or nitrogen atoms on the benzene ring or heterocycle to form a 5- or 6-membered carbon ring or a 5- or 6-membered heterocycle, where the heterocycle consists of an oxygen atom, a sulfur atom, and a nitrogen atom (the nitrogen atom is C １ ~C ６ Alkyl, C ２ ~C ６ Alkenil, C ２ ~C ６ Alkinyl, or C ３ ~C ６ It comprises one or two heteroatoms selected from the group consisting of (which may be substituted with cycloalkyl groups), and the carbocyclic or heterocyclic ring may be substituted with one or more halogens, The aforementioned 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-tetrazoline, pyridine, pyrimidine, pyrazine, pyridazine, 1,3,5-triazine, 1,2,4-triazine, benzothiophene, benzofuran, indole, benzothiazole, benzimidazole, benzoisoxazole, benzoisothiazole, indazole, benzoxazole, quinoline, isoquinoline, quinoxaline, phthalazine, cinnoline, or quinazoline. The aforementioned heterocyclils include 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, pyridadinyl, 1,3,5-triazinyl, 1,2,4-triazinyl, benzothienyl, benzof These are lyl, indolyl, benzothiazolyl, benzimidazolyl, benzoisoxazolyl, benzoisothiazolyl, indazolyl, benzoxazolyl, quinolyl, isoquinolyl, quinoxalinyl, phthalazinyl, cinnolinyl, quinazolinyl, oxylanil, oxetanyl, tetrahydrofuranil, tetrahydrothienyl, 1,1-dioxytetrahydrothienyl, tetrahydropyranil, tetrahydrothiopyranil, 1,3-dioxanil, 2-oxo-1,3-dioxolyl, or 2,5-dioxopyrrolidinyl. Z ３ is a halogen atom, Z ２ Phenyl, tri-C which may be substituted with one or more substituents selected from １ ~C ６ Alkylsilyl, C １ ~C ６ C may be substituted with alkyldiphenylsilyl or one or more halogen atoms. １ ~C ６ Alkoxy, Z ２ Phenylcarbonyloxy or Z which may be substituted with one or more substituents selected from ２ A phenylsulfonyl which may be substituted with one or more substituents selected from, Z ４ is, Z ２ Phenyl or Z which may be substituted with one or more substituents selected from ２ A heterocyclyl which may be substituted with one or more substituents selected from, Z ５ is, Z ２ A phenoxy which may be substituted with one or more substituents selected from, Z ６ is, Ji (C １ ~C ６ Selected from the group consisting of alkyl)aminocarbonyl, hydroxy, amino, cyano, and nitro, Z ７ is halogen, C １ ~C ６ Alkyl, C ２ ~C ６ Alkenil, C ２ ~C ６ Alkinyl, C ３ ~C ６ Cycloalkyl, Halo C １ ~C ６ Alkyl, Halo C ３ ~C ６ Cycloalkyl, C １ ~C ６ Alkoxy, Halo C １ ~C ６ Alkoxy, C １ ~C ６ Alkylthio, Halo C １ ~C ６ Alkylthio, C １ ~C ６ Alkyl sulfinyl, Halo C １ ~C ６ Alkyl sulfinyl, C １ ~C ６ Alkyl sulfonyl, Halo C １ ~C ６ Alkyl sulfonyl, (C １ ~C ６ Alkyl)carbonyl, (halo C １ ~C ６ (Alkyl)carbonyl, (C １ ~C ６ Alkoxy) carbonyl, carboxyl, mono(C) １ ~C ６ Alkyl)aminocarbonyl, may be the same or different (C １ ~C ６ Selected from the group consisting of alkyl)aminocarbonyl, hydroxyl group, amino, cyano, and nitro, Z ８ is, Z ２ Phenylthio, Z which may be substituted with one or more substituents selected from ２ Phenyl sulfinyl which may be substituted with one or more substituents selected from and Z ２ Selected from the group consisting of phenylsulfonyl which may be substituted with one or more substituents selected from, R １１ and R １２ These are, independently of each other, hydrogen atoms and C １ ~C ６ Alkyl, and Z ２ Selected from the group consisting of phenyl which may be substituted with one or more substituents selected from, R １３ is a hydrogen atom, or C １ ~C ６ Selected from the group consisting of alkyl groups, R １４ is a hydrogen atom, or Z ７ A phenyl which may be substituted with one or more substituents selected from, R ３ and R ４ These are hydrogen atoms and C, which are independent of each other. １ ~C ６ Alkyl, Halo C １ ~C ６ Alkyl, C １ ~C ６ Cycloalkyl, Halo C １ ~C ６ Cycloalkyl, C １ ~C ６ Alkoxy, Halo C １ ~C ６ It is an alkoxy, halogen, or cyano, Or, R ３ and R ４ They can bond to each other to form a 3- to 7-membered ring. R ５ and R ６ These are independent of each other: hydrogen atoms, halogens, and C １ ~C ６ Alkyl, Halo C １ ~C ６ Alkyl, C ２ ~C ６ Alkenil, C ２ ~C ６ Alkinyl, C ３ ~C ６ Cycloalkyl, Halo C ３ ~C ６ Cycloalkyl, hydroxy C １ ~C ６ Alkyl, C １ ~C ６ Alkoxy C １ ~C ６ Alkyl, Halo C １ ~C ６ Alkoxy C １ ~C ６ Alkyl, C １ ~C ６ Alkylthio C １ ~C ６ Alkyl, Halo C １ ~C ６ Alkylthio C １ ~C ６ Alkyl, mono(C) １ ~C ６ Alkyl) Amino C １ ~C ６ Alkyl, may be the same or different (C １ ~C ６ Alkyl) Amino C １ ~C ６ Alkyl, Z ２ Phenyl, Z which may be substituted with one or more substituents selected from ２ A heterocycline, Z which may be substituted with one or more substituents selected from ４ C substituted with one more selected substituent １ ~C ６ Alkyl, Z ５ C substituted with one substituent selected from １ ~C ６ Alkyl, (C １ ~C ６ Alkyl)carbonyl, (halo C １ ~C ６ Alkyl)carbonyl, Z ２ Phenylcarbonyl, which may be substituted with one or more substituents selected from (C １ ~C ６ Alkoxy)carbonyl, (halo C １ ~C ６ Alkoxy) carbonyl, carboxyl, -NR １１ R １２ , C １ ~C ６ Alkoxy, Halo C １ ~C ６ Alkoxy, Z ２ Phenoxy, C which may be substituted with one or more substituents selected from １ ~C ６ Alkylthio, Halo C １ ~C ６ Alkylthio, Z ２ Phenylthio, C which may be substituted with one or more substituents selected from １ ~C ６ Alkyl sulfonyl, Halo C １ ~C ６ Alkyl sulfonyl, mono(C) １ ~C ６ Alkyl)amino, di(C) １ ~C ６ Alkyl)amino, (C １ ~C ６ Alkyl)carbonyloxy, hydroxyl group, amino, cyano, or nitro, Or, R on the same carbon ５ and R ６ These atoms are bonded to each other, forming an oxygen atom, a sulfur atom, and a nitrogen atom (the nitrogen atom is C １ ~C ６ Alkyl, C ２ ~C ６ Alkenil, C ２ ~C ６ Alkinyl, or C ３ ~C ６ It may be interrupted by one or two heteroatoms selected from the group consisting of (which may be substituted with cycloalkyl groups), and may optionally form a 3- to 7-membered ring, or it may form an olefin. Or, R ５ and R ６ R on different carbons ５ or R ６ It combines with an oxygen atom, a sulfur atom, and a nitrogen atom (the nitrogen atom is C １ ~C ６ Alkyl, C ２ ~C ６ Alkenil, C ２ ~C ６ Alkinyl, or C ３ ~C ６ C may be interrupted by one or two heteroatoms selected from the group consisting of (which may be substituted with cycloalkyl groups), and may be optionally substituted. １ ~C ４ Alkilen, Halo C １ ~C ４ Alkylene, C ２ ~C ４ Alkenylene, or Halo C ２ ~C ４ Alkenylenes can form 3- to 8-membered rings. Or, R ５ and R ６ R on adjacent carbons ５ or R ６ They can come together to form a bond, R ７ C is a hydrogen atom. １ ~C ６ Alkyl, Halo C １ ~C ６ Alkyl, C ３ ~C ６ Cycloalkyl, Halo C ３ ~C ６ Cycloalkyl, C ２ ~C ６ Alkenil, Halo C ２ ~C ６ Alkenil, C ２ ~C ６ Alkinyl, HydroxyC １ ~C ６ Alkyl, C １ ~C ６ Alkoxy C １ ~C ６ Alkyl, Halo C 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, Z which may be substituted with 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, (Halo C) １ ~C ６ Alkyl)carbonyl C １ ~C ６ Alkyl, (C １ ~C ６ Alkoxy) Carbonyl C １ ~C ６ Alkyl, (Halo C) １ ~C ６ Alkoxy) Carbonyl C １ ~C ６ Alkyl, (C １ ~C ６ Alkyl)carbonyl, (halo C 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, Z which may be substituted with one or more substituents selected from ２ A heterocyclylcarbonyl, which may be substituted with one or more substituents selected from (C １ ~C ６ Alkoxy)carbonyl, (halo C １ ~C ６ Alkoxy) carbonyl, Z ２ Phenoxycarbonyl, aminocarbonyl, mono(C) may be substituted with one or more substituents selected from １ ~C ６ Alkyl)aminocarbonyl, monohalo(C １ ~C ６ Alkyl)aminocarbonyl, may be the same or different (C １ ~C ６ Alkyl)aminocarbonyl, which may be the same or different halo(C) １ ~C ６ Alkyl)aminocarbonyl, (C １ ~C ６ Alkylthio)carbonyl, (halo C １ ~C ６ Alkylthio)carbonyl, C １ ~C ６ Alkyl sulfonyl, Halo C １ ~C ６ Alkyl sulfonyl, Z ２ Phenylsulfonyl, which may be substituted with one or more substituents selected from C １ ~C ６ Alkylthio C １ ~C ６ Alkyl, Halo C 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 Alkyl sulfinyl C １ ~C ６ Alkyl, Halo C １ ~C ６ Alkyl sulfinyl C １ ~C ６ Alkyl, C １ ~C ６ Alkylsulfonyl C １ ~C ６ Alkyl, Halo C １ ~C ６ Alkylsulfonyl C １ ~C ６ Alkyl, cyano, amino, or hydroxy, X consists of hydrogen atoms, halogens, and C, all independent of each other. １ ~C ６ Alkyl, C ２ ~C ６ Alkenil, C ２ ~C ６ Alkinyl, C ３ ~C ６ Cycloalkyl, Halo C １ ~C ６ Alkyl, Halo C ２ ~C ６ Alkenil, Halo C ２ ~C ６ Alkinil, Halo C ３ ~C ６ Cycloalkyl, C １ ~C ６ Alkoxy, Halo 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, Z which may be substituted with one or more substituents selected from ２ Heterocyclylcarbonyloxy, which may be substituted with one or more substituents selected from (C １ ~C ６ Alkoxy) carbonyl oxy, (C １ ~C ６ Alkylthio)carbonyloxy, C １ ~C ６ Alkyl sulfonyl oxy, Halo C １ ~C ６ Alkyl sulfonyl oxy, phenyl sulfonyl oxy, diC １ ~C ６ Alkylphosphoroxy, TriC １ ~C ６ Alkylsilyloxy, C １ ~C ６ Alkoxy C １ ~C ６ Alkyl, C １ ~C ６ Alkylthio, Halo C １ ~C ６ Alkylthio, C １ ~C ６ Alkyl sulfinyl, Halo C １ ~C ６ Alkyl sulfinyl, C １ ~C ６ Alkyl sulfonyl, Halo C １ ~C ６ Alkyl sulfonyl, Z ２ Phenyl, Z which may be substituted with one or more substituents selected from ２ A heterocycline, Z which may be substituted with one or more substituents selected from ２ Phenoxy, Z which may be substituted with one or more substituents selected from ２ Phenylthio, Z which may be substituted with one or more substituents selected from ２ Phenylsulfinyl, Z which may be substituted with one or more substituents selected from ２ Phenylsulfonyl, di(C) which may be substituted with one or more substituents selected from 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, (halo C １ ~C ６ Alkyl)carbonyl, Z ２ Phenylcarbonyl, which may be substituted with one or more substituents selected from (C １ ~C ６ Alkoxy) carbonyl, carboxyl, mono(C) １ ~C ６ Alkyl)aminocarbonyl, may be the same or different (C １ ~C ６ Alkyl)aminocarbonyl, Z ２ Phenylaminocarbonyl, phenyl(C) which may be substituted with one or more substituents selected from １ ~C ６ Alkylamino)carbonyl, Z ４ Substituted by one substituent selected from (C １ ~C ６ Alkylamino)carbonyl, hydroxy, amino, cyano, or nitro, Alternatively, two X atoms linked to adjacent carbon or nitrogen atoms on a benzene ring or heterocycle, together with the ring atom to which they are linked, form a 4- to 6-membered carbon ring or heterocycle, the heterocycle 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 Alkenil, C ２ ~C ６ Alkinyl, or C ３ ~C ６ It may also be substituted with a cycloalkyl group. Y consists of hydrogen atoms, halogens, and C, all independent of each other. １ ~C ６ Alkyl, C ２ ~C ６ Alkenil, C ２ ~C ６ Alkinyl, C ３ ~C ６ Cycloalkyl, Halo C １ ~C ６ Alkyl, Halo C ２ ~C ６ Alkenil, Halo C ２ ~C ６ Alkinil, Halo C ３ ~C ６ Cycloalkyl, C １ ~C ６ Alkoxy, Halo 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, Z which may be substituted with one or more substituents selected from ２ Heterocyclylcarbonyloxy, which may be substituted with one or more substituents selected from (C １ ~C ６ Alkoxy) carbonyl oxy, (C １ ~C ６ Alkylthio)carbonyloxy, C １ ~C ６ Alkyl sulfonyl oxy, Halo C １ ~C ６ Alkyl sulfonyl oxy, phenyl sulfonyl oxy, diC １ ~C ６ Alkylphosphoroxy, TriC １ ~C ６ Alkylsilyloxy, C １ ~C ６ Alkoxy C １ ~C ６ Alkyl, C １ ~C ６ Alkylthio, Halo C １ ~C ６ Alkylthio, C １ ~C ６ Alkyl sulfinyl, Halo C １ ~C ６ Alkyl sulfinyl, C １ ~C ６ Alkyl sulfonyl, Halo C １ ~C ６ Alkyl sulfonyl, Z ２ Phenyl, Z which may be substituted with one or more substituents selected from ２ A heterocycline, Z which may be substituted with one or more substituents selected from ２ Phenoxy, Z which may be substituted with one or more substituents selected from ２ Phenylthio, Z which may be substituted with one or more substituents selected from ２ Phenylsulfinyl, Z which may be substituted with one or more substituents selected from ２ Phenylsulfonyl, di(C) which may be substituted with one or more substituents selected from 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, (halo C １ ~C ６ Alkyl)carbonyl, Z ２ Phenylcarbonyl, which may be substituted with one or more substituents selected from (C １ ~C ６ Alkoxy) carbonyl, carboxyl, -NR １１ R １２ , hydroxy, amino, cyano, or nitro, Alternatively, the two Y atoms may combine with adjacent carbon or nitrogen atoms on the benzene ring to form a five- or six-membered carbon ring or a five- or six-membered heterocycle, where the heterocycle consists of an oxygen atom, a sulfur atom, and a nitrogen atom (the nitrogen atom is C １ ~C ６ Alkyl, C ２ ~C ６ Alkenil, C ２ ~C ６ Alkinyl, or C ３ ~C ６ It may be substituted with a cycloalkyl group.) It contains one or two heteroatoms selected from the group consisting of the following, and the carbon ring or heterocycle may be substituted with one or more halogens. A compound represented by or a salt thereof.

2. General formula [1a] 【Chemistry 2】 {In the formula, E is -CH} ２ - and W is an oxygen atom or a sulfur atom, m is 0, n is 0, 1, or 3. R １ Fluorocarbon C １ ~C ６ It is alkyl, R ２ C is a hydrogen atom. １ ~C ６ Alkoxy C １ ~C ６ Alkyl, or (C １ ~C １２ It is an alkoxy carbonyl, R ３ and R ４ It is a hydrogen atom, X １ , X ２ , X ３ and X ４ These are hydrogen atoms, halogens, and C, which are independent of each other. １ ~C ６ Alkyl, Halo C 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) which may be substituted with one or more substituents selected from １ ~C ６ Alkoxy) carbonyl oxy, (C １ ~C ６ Alkylthio)carbonyloxy, C １ ~C ６ Alkyl sulfonyl oxy, Halo C １ ~C ６ Alkyl sulfonyl oxy, phenyl sulfonyl oxy, diC １ ~C ６ Alkylphosphoroxy, 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 These are hydrogen atoms or halo C, independently of each other. １ ~C ６ It is alkyl, Said Z ２ The compound according to claim 1, or a salt thereof, represented by {is nitro}.

3. General formula [1a] 【Transformation 3】 {In the formula, E is -CH} ２ - and W is an oxygen atom or a sulfur atom, m is 0, n is 2, R １ Fluorocarbon C １ ~C ６ It is alkyl, R ２ is a hydrogen atom, C ２ -C ６ alkynyl, Z ４ substituted by one substituent selected from C 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, (halo C 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 alkylhalo(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 C 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[[ID=!16]] 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 Z ２ heterocyclyloxycarbonyl optionally substituted by one or more substituents selected from Z, C ３ ~C ６ cycloalkyl(C １ ~C ６ alkoxy)carbonyl, Z ４ (C １ ~C ６ alkoxy)carbonyl substituted by one substituent selected from Z, (cyanoC １ ~C ６ alkoxy)carbonyl, (hydroxyC １ ~C ６ alkoxy)carbonyl, C １ ~C ６ alkoxy(C １ ~C ６ alkoxy)carbonyl, C １ ~C ６ (C １ ~C ６ alkoxy)carbonyl substituted by one or more substituents selected from alkoxy, (C １ ~C It should be noted that there may be some inaccuracies in the translation as the original text seems to be incomplete or contains some unclear notations. If possible, it would be beneficial to have more context or clarify the text for a more precise translation. 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 Alkylsulfonyloxy (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 Alkylsulfonyl (C １ ~C ６ Alkoxy) carbonyl, (C １ ~C ６ Alkylthio)carbonyl, mono(C) １ ~C ６ Alkyl)aminocarbonyl, the same or different di(C) １ ~C ６ Alkyl)aminocarbonyl, C １ ~C ６ Alkyl sulfonyl, Halo C １ ~C ６ Alkyl sulfonyl, or C ３ ~C ６ It is a cycloalkylsulfonyl, R ３ and R ４ It is a hydrogen atom, X １ , X ２ , X ３ and X ４ These are hydrogen atoms, halogens, and C, which are independent of each other. １ ~C ６ Alkyl, C ３ ~C ６ Cycloalkyl, Halo C １ ~C ６ Alkyl, C １ ~C ６ Alkoxy, Halo C １ ~C ６ Alkoxy, C ２ ~C ６ Alkynyloxy, (C １ ~C ６ Alkyl)carbonyloxy, phenylcarbonyloxy, (C １ ~C ６ Alkoxy) Carbonyl Oxy, C １ ~C ６ Alkyl sulfonyl oxy, Halo C １ ~C ６ Alkyl sulfonyl oxy, C １ ~C ６ Alkylthio, C １ ~C ６ Alkyl sulfonyl, phenyl, the same or different 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 It is an alkoxy) carbonyl, hydroxyl, cyano, or nitro group. Or, X １ , X ２ , X ３ and X ４ It may combine with adjacent carbon atoms on the benzene ring to form a 5 or 6-membered carbocyclic or 5 or 6-membered heterocyclic ring, where the heterocyclic ring contains one or two heteroatoms selected from a sulfur atom and a nitrogen atom. Y １ , Y ２ , Y ３ and Y ４ These are hydrogen atoms, halogens, and C, which are independent of each other. １ ~C ６ Alkyl, Halo C １ ~C ６ Alkyl, C １ ~C ６ It is an alkoxy or hydroxyl group, Or, Y １ and Y ２ , Y ２ and Y ３ , and Y ３ and Y ４ These may also form a 4-6 membered carbon ring together with the carbon atoms they link to. Said Z ２ is C １ ~C ６ Alkyl, C １ ~C ６ It is an alkoxy or nitro, The compound or salt thereof according to claim 1, wherein the heterocyclyl is thienyl, furyl, pyrrolyl, oxyranil, oxetanil, tetrahydrofuranil, tetrahydrothienyl, 1,1-dioxytetrahydrothienyl, tetrahydropyranil, tetrahydrothiopyranil, 1,3-dioxanil, 2-oxo-1,3-dioxolyl, or 2,5-dioxopyrrolidinyl.

4. n is 2, R １ It 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, (halo C １ ~C ３ Alkoxy) carbonyl, (C ３ ~C ４ Cycloalkyloxy)carbonyl, (C ２ ~C ３ Alkynyloxycarbonyl, 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 Alkyl sulfonyl, or (C １ ~C ４ It is an alkylthio)carbonyl, X １ This is a fluorine atom, a chlorine atom, or a methyl atom. X ２ and X ３ It is a hydrogen atom, X ４ These are hydrogen atoms, fluorine atoms, chlorine atoms, methyl, trifluoromethyl, or methoxy atoms. Y １ , Y ２ , Y ３ and Y ４ It is a hydrogen atom, The compound or salt thereof according to claim 3, wherein the heterocyclyl is oxiranil, oxetanil, tetrahydrofuranil, or tetrahydropyranil.

5. General formula [1b] 【Chemistry 4】 {In the formula, Het is 【Transformation 5】 Selected from, E is -CH ２ - and W is an oxygen atom, m is 0, n is between 1 and 2. R １ Fluorocarbon C １ ~C ６ It is alkyl, R ２ is a hydrogen atom or (C １ ~C １２ It is an alkoxy carbonyl, R ３ and R ４ It is a hydrogen atom, Y １ , Y ２ , Y ３ and Y ４ The compound or salt thereof according to claim 1, represented as {where is a hydrogen atom}.

6. Het is either Het-1 or Het-2. n is 2, R １ It is trifluoromethyl, R ２ is a hydrogen atom or (C ２ ~C ６ The compound or salt thereof according to claim 5, wherein it is an alkoxy carbonyl.

7. 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-dihydroisoindole-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-fluoro-1,3-dihydroisoindole-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-chloro-1,3-dihydroisoindole-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-bromo-1,3-dihydroisoindole-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-methyl-1,3-dihydroisoindole-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-phenyl-1,3-dihydroisoindole-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-cyano-1,3-dihydroisoindole-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-hydroxy-1,3-dihydroisoindole-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-methoxy-1,3-dihydroisoindole-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-acetoxy-1,3-dihydroisoindole-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-benzoyloxy-1,3-dihydroisoindole-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-(4-nitro-benzoyl)oxy-1,3-dihydroisoindole-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-methoxycarbonyloxy-1,3-dihydroisoindole-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-(2-propylthio)carbonyloxy-1,3-dihydroisoindole-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-(1H-imidazole-1-yl-carbonyloxy)-1,3-dihydroisoindole-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-(pyrrolidine-1-yl-carbonyloxy)-1,3-dihydroisoindole-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-methanesulfonyloxy-1,3-dihydroisoindole-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-trifluoromethanesulfonyloxy-1,3-dihydroisoindole-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-phenylsulfonyloxy-1,3-dihydroisoindole-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-diethylphosphorooxy-1,3-dihydroisoindole-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-tert-butyldimethylsilyloxy-1,3-dihydroisoindole-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-propargyloxy-1,3-dihydroisoindole-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-allyloxy-1,3-dihydroisoindole-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-benzyloxy-1,3-dihydroisoindole-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-cyclopropylmethyloxy-1,3-dihydroisoindole-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-amino-1,3-dihydroisoindole-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-acetylamino-1,3-dihydroisoindole-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-bisacetylamino-1,3-dihydroisoindole-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-trifluoromethanesulfonylamino-1,3-dihydroisoindole-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-(isoindorin-1,3-dione-2-yl)-1,3-dihydroisoindole-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-6-fluoro-1,3-dihydroisoindole-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-6-methyl-1,3-dihydroisoindole-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-6-hydroxy-1,3-dihydroisoindole-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-6-methoxy-1,3-dihydroisoindole-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-6-acetoxy-1,3-dihydroisoindole-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-6-trifluoromethanesulfonyloxy-1,3-dihydroisoindole-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-6-propargyloxy-1,3-dihydroisoindole-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-6-nitro-1,3-dihydroisoindole-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-6-(isoindorin-1,3-dione-2-yl)-1,3-dihydroisoindole-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5-bromo-1,3-dihydroisoindole-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5-methyl-1,3-dihydroisoindole-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5-hydroxy-1,3-dihydroisoindole-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5-methoxy-1,3-dihydroisoindole-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5-acetoxy-1,3-dihydroisoindole-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5-propargyloxy-1,3-dihydroisoindole-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-4-hydroxy-1,3-dihydroisoindole-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-4-methoxy-1,3-dihydroisoindole-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-4-acetoxy-1,3-dihydroisoindole-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-4-trifluoromethanesulfonyloxy-1,3-dihydroisoindole-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-4-propargyloxy-1,3-dihydroisoindole-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-4-nitro-1,3-dihydroisoindole-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5-fluoro-6-nitro-1,3-dihydroisoindole-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5,6-dibromo-4-methoxy-1,3-dihydroisoindole-1-one, N-[2-(N-trifluoromethanesulfonyl)amino-5-trifluoromethyl-benzyl]-1,3-dihydroisoindole-1-one, N-[2-(N-trifluoromethanesulfonyl)amino-5-trifluoromethyl-benzyl]-5-bromo-1,3-dihydroisoindole-1-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-1,3-dihydroisoindole-1-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-7-amino-1,3-dihydroisoindole-1-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-5-bromo-1,3-dihydroisoindole-1-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)amino-5-trifluoromethyl-benzyl]-1,3-dihydroisoindole-1-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)amino-5-trifluoromethyl-benzyl]-5-bromo-1,3-dihydroisoindole-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-methoxymethyloxy-1,3-dihydroisoindole-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-8-fluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-8-chloro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-8-bromo-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-8-iodo-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-8-methyl-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-8-cyclopropyl-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-8-phenyl-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-8-trifluoromethyl-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-8-cyano-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-8-hydroxy-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-8-methoxy-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-8-acetoxy-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-8-difluoromethoxy-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-8-trifluoromethoxy-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-8-propargyloxy-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-8-dimethylamino-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-8-methoxycarbonyl-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-fluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-chloro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-bromo-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-iodo-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-methyl-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-ethyl-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-tert-butyl-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-phenyl-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-trifluoromethyl-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-nitro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-hydroxy-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-methoxy-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-ethoxycarbonyloxy-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-benzoyloxy-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-propargyloxy-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-trifluoromethoxy-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-6-fluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-6-chloro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-6-bromo-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-6-iodo-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-6-methyl-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-6-trifluoromethyl-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-6-methoxy-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5-fluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5-chloro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5-methyl-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5-nitro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5-methoxy-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5-acetoxy-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5-methanesulfonyloxy-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5-trifluoromethoxy-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5-ethoxycarbonyloxy-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5-benzoyloxy-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5-propargyloxy-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-8-fluoro-7-methyl-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-8-fluoro-7-nitro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7,8-dichloro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-8-chloro-7-methyl-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-6,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-8-fluoro-6-methyl-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-6-cyclopropyl-8-fluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-6-cyano-8-fluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-6,8-dichloro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-6,8-dimethyl-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5-chloro-8-fluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5-bromo-8-fluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-8-fluoro-5-methyl-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-8-fluoro-5-trifluoromethyl-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-8-fluoro-5-methoxy-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5-chloro-8-fluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5,8-dichloro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5-fluoro-8-hydroxy-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5-fluoro-8-methoxy-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5-fluoro-8-methanesulfonyloxy-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5-fluoro-8-dimethylamino-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5-fluoro-8-(N-morpholinyl)-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5-fluoro-8-methylthio-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5-fluoro-8-methanesulfonyl-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5,8-bis(methanesulfonyl)-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-6,7-dichloro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-6-fluoro-7-methyl-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-6-chloro-7-methyl-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-6-fluoro-7-nitro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-6-chloro-7-nitro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5,6-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-6,8-difluoro-7-nitro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-6,8-dichloro-7-nitro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-3,4-dihydrobenzo[h]isoquinoline-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-3,4-dihydrobenzo[g]isoquinoline-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7,8-dihydrothiazolo[4,5-h]isoquinoline-9(6H)-one, N-[2-(N-methyl-N-trifluoromethanesulfonyl)aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-propargyl-N-trifluoromethanesulfonyl)aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-(4-methoxybenzyl)-N-trifluoromethanesulfonyl)aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-[N-[3-(1,3-dioxan-2-yl)propanyl]-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-cyanomethyl-N-trifluoromethanesulfonyl)aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-ethoxymethyl-N-trifluoromethanesulfonyl)aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-[N-(isopropyloxycarbonyloxymethyl)-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-acetyl-N-trifluoromethanesulfonyl)aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-ethylcarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-[N-(1-propylcarbonyl)-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-[N-(2-propylcarbonyl)-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-[N-(2-methyl-1-propylcarbonyl)-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-[N-(2,2-dimethyl-1-propylcarbonyl)-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-chloromethylcarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-cyclopropylcarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-8-fluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-cyclopropylcarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-8-chloro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-cyclopropylcarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-6-chloro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-cyclopropylcarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-cyclopropylcarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-8-fluoro-5-methyl-3,4-dihydroisoquinoline-1(2H)-one, N-[2-[N-(2-methyl-cyclopropyl)carbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-[N-(2,2-dimethylcyclopropyl)carbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-[N-(2,2-dichloro-1-methyl-cyclopropyl)carbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-cyclobutylcarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-cyclopentylcarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-cyclohexylcarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-acryloyl-N-trifluoromethanesulfonyl)aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-[N-(prop-1-ene-1-yl)carbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-[N-(2-methyl-prop-1-en-1-yl)carbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-[N-(prop-1-en-2-yl)carbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-[N-(3-ethoxyacryloyl)-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-benzoyl-N-trifluoromethanesulfonyl)aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-[N-(furan-2-yl)carbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-[N-(thiophen-2-yl)carbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-[N-(1-methyl-1H-pyrrole-2-yl)carbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-[N-(furan-3-yl)carbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-[N-(tetrahydrofuran-2-yl)carbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-[N-(tetrahydrofuran-3-yl)carbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-[N-(tetrahydropyran-4-yl)carbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-[N-(2-cyclopropylacetyl)-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-[N-(2-hydroxyethyl)carbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-methoxyacetyl-N-trifluoromethanesulfonyl)aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-ethoxyacetyl-N-trifluoromethanesulfonyl)aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-[N-(2-methoxyethyl)carbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-[N-(2-tert-butyldimethylsilyloxyethyl)carbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-acetoxyacetyl-N-trifluoromethanesulfonyl)aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-methylsulfylacetyl-N-trifluoromethanesulfonyl)aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-ethylsulfylacetyl-N-trifluoromethanesulfonyl)aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-[N-(1-methylsulfylethyl)carbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-methoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-8-fluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-8-cyclopropyl-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-8-cyano-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-8-hydroxy-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-8-phenyl-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-5-methyl-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-8-fluoro-6-methyl-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-6-cyclopropyl-8-fluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-6-cyano-8-fluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-5-bromo-8-fluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-8-fluoro-5-methyl-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-8-fluoro-5-trifluoromethyl-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-8-fluoro-5-methoxy-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-8-chloro-5-fluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-8-dimethylamino-5-fluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-5-fluoro-8-(N-morpholinyl)-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-5-fluoro-8-methylthio-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-5,8-bis(methylthio)-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-5-fluoro-8-methanesulfonyl-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-5,6-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-[N-(1-propyl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-[N-(2-propyl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-[N-(1-butyl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-[N-(2-methyl-1-propyl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-[N-(2-butyl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-[N-(1,1-dimethyl-ethyl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-[N-(1-pentyl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-[N-(1-hexyl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-[N-(1-heptyl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-[N-(2,2-dimethyl-1-propyl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-[N-(chloromethyl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-[N-(trichloromethyl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-[N-(1-chloroethyl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-[N-(2-fluoroethyl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-8-fluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-[N-(2-fluoroethyl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-[N-(2,2-difluoroethyl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-3,4-dihydroisoquinoline-1(2H)-one, N-[2-[N-(2,2-difluoroethyl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-8-fluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-[N-(2,2-difluoroethyl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-[N-(2,2,2-trifluoroethyl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-[N-(2-chloroethyl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-[N-(2,2-difluoro-1-methyl-ethyl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-[N-(2,2,2-trifluoro-1-methyl-ethyl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-[N-(1,3-difluoropropane-2-yl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-cyclopropyloxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-cyclobutyloxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-cyclopentyloxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-cyclohexyloxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-allyloxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-[N-(buto-3-en-2-yl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-[N-(2-methylallyl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-[N-(3-methylbuto-2-en-1-yl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-propargyloxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-[N-(buto-3-in-2-yl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-phenoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-[N-(4-nitrophenoxy)carbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-[N-(oxetan-3-yl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-3,4-dihydroisoquinoline-1(2H)-one, N-[2-[N-(oxetan-3-yl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-8-fluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-[N-(oxetan-3-yl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-[N-(tetrahydrofuran-3-yl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-3,4-dihydroisoquinoline-1(2H)-one, N-[2-[N-(tetrahydrofuran-3-yl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-[N-((S)-tetrahydrofuran-3-yl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-[N-((R)-tetrahydrofuran-3-yl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-[N-(tetrahydrothiophen-3-yl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-[N-(1,1-dioxidetetrahydrothiophen-3-yl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-[N-(tetrahydro-2H-pyran-3-yl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-[N-(tetrahydro-2H-pyran-4-yl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-[N-(1,3-dioxan-5-yl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-[N-(2,2-dimethyl-1,3-dioxan-5-yl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-[N-(tetrahydro-2H-thiopyran-4-yl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-[N-(1,1-dioxidetetrahydro-2H-thiopyran-4-yl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-[N-(2,5-dioxopyrrolidine-1-yl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-[N-(cyclopropylmethyloxy)carbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-benzyloxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-[N-(oxiran-2-ylmethyl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-[N-[(2-methyloxylan-2-yl)methyl]oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-[N-[(3,3-dimethyloxylan-2-yl)methyl]oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-[N-[1-(oxylan-2-yl)ethyl]oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-[N-(oxetane-2-ylmethyl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-(oxetane-3-ylmethyl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-[N-[(tetrahydrofuran-2-yl)methyl]oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-[N-[(tetrahydrofuran-3-yl)methyl]oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-[N-[(tetrahydro-2H-pyran-2-yl)methyl]oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-[N-[(tetrahydro-2H-pyran-4-yl)methyl]oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-[N-[(2-oxo-1,3-dioxolan-4-yl)methyl]oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-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-dihydroisoquinoline-1(2H)-one, N-[2-[N-(2-cyanoethoxy)carbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-[N-(2-hydroxyethoxy)carbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-[N-(2-methoxyethoxy)carbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-[N-(1-methyl-2-methoxy-ethoxy)carbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-[N-(1,3-dimethoxypropane-2-yl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-[N-[2-(tert-butyldiphenylsilyloxy)ethyl]oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-[N-[2-(acetyloxy)ethoxy]carbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-[N-[2-(methanesulfonyloxy)ethoxy]carbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-[N-(2-oxopropyl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-[N-(methoxycarbonylmethoxycarbonyl)oxycarbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-[N-(2-methylthioethoxy)carbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-[N-(2-methanesulfonyl-ethoxy)carbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-[N-(2-propylthio)carbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-3,4-dihydroisoquinoline-1(2H)-one, N-[2-[N-(2-propylthio)carbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-8-fluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-ethylthio-carbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-[N-(2-propylthio)carbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-[N-(2-butyl)thio-carbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-methylaminocarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-[N-(2-propylamino)carbonyl-N-trifluoromethanesulfonyl]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-dimethylaminocarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-methanesulfonyl-N-trifluoromethanesulfonyl)aminobenzyl]-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-methanesulfonyl-N-trifluoromethanesulfonyl)aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-methanesulfonyl-N-trifluoromethanesulfonyl)aminobenzyl]-5-fluoro-8-hydroxy-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-ethanesulfonyl-N-trifluoromethanesulfonyl)aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-[N,N-bis(trifluoromethanesulfonyl)]aminobenzyl]-8-hydroxy-3,4-dihydroisoquinoline-1(2H)-one, N-[2-[N,N-bis(trifluoromethanesulfonyl)]aminobenzyl]-8-propargyloxy-3,4-dihydroisoquinoline-1(2H)-one, N-[2-[N,N-bis(trifluoromethanesulfonyl)]aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-cyclopropanesulfonyl-N-trifluoromethanesulfonyl)aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, Sodium [2-[(5,8-difluoro-1-oxo-3,4-dihydroisoquinoline-2(1H)-yl)methyl]phenyl][(trifluoromethyl)sulfonyl]amide, Potassium [2-[(5,8-difluoro-1-oxo-3,4-dihydroisoquinoline-2(1H)-yl)methyl]phenyl][(trifluoromethyl)sulfonyl]amide, N-[2-(N-trifluoromethanesulfonyl)amino-3-chlorobenzyl]-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)amino-4-methylbenzyl]-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)amino-4-methoxybenzyl]-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)amino-5-fluorobenzyl]-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)amino-5-chlorobenzyl]-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)amino-5-bromobenzyl]-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)amino-5-methylbenzyl]-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)amino-6-chlorobenzyl]-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)amino-3,5-dichlorobenzyl]-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)amino-5-chlorobenzyl]-8-chloro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)amino-5-chlorobenzyl]-6-chloro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)amino-3-fluorobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)amino-3-chlorobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)amino-3-methylbenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)amino-4-fluorobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)amino-5-fluorobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)amino-5-chlorobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)amino-5-methylbenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)amino-5-hydroxybenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)amino-5-methoxybenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)amino-6-fluorobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)amino-6-chlorobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)amino-6-methylbenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminonaphthalen-3-ylmethyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)amino-5-chlorobenzyl]-8-chloro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)amino-3-fluorobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)amino-3-chlorobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)amino-3-methyl-benzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)amino-4-fluorobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)amino-5-fluorobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)amino-5-chlorobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)amino-5-methylbenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)amino-5-trifluoromethyl-benzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)amino-5-hydroxybenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)amino-5-methoxybenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)amino-6-fluorobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)amino-6-chlorobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)amino-6-methyl-benzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminonaphthalen-3-yl-methyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-pento-1-yloxycarbonyl-N-trifluoromethanesulfonyl)amino-4-fluorobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-pento-1-yloxycarbonyl-N-trifluoromethanesulfonyl)amino-5-fluorobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-pento-1-yloxycarbonyl-N-trifluoromethanesulfonyl)amino-6-fluorobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-2,3,4,5-tetrahydro-1H-2-benzazepine-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-9-chloro-2,3,4,5-tetrahydro-1H-2-benzazepine-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-9-methyl-2,3,4,5-tetrahydro-1H-2-benzazepine-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-fluoro-2,3,4,5-tetrahydro-1H-2-benzazepine-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-chloro-2,3,4,5-tetrahydro-1H-2-benzazepine-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-7-methyl-2,3,4,5-tetrahydro-1H-2-benzazepine-1-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-4,5-dihydro-6H-thieno[2,3-c]pyrrole-6-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-2-bromo-4,5-dihydro-6H-thieno[2,3-c]pyrrole-6-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-2-(methylthio)-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidine-5-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5,6-dihydrofuran[2,3-c]pyrimidine-7(4H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5,6-dihydrothieno[2,3-c]pyridine-7(4H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-6,7-dihydrothieno[3,2-c]pyridine-4(5H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-3-methyl-5,6-dihydroisoxazolo[5,4-c]pyridine-7(4H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-2-methyl-6,7-dihydrooxazolo[5,4-c]pyridine-4(5H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-6,7-dihydrooxazolo[4,5-c]pyridine-4(5H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-2-methyl-6,7-dihydrooxazolo[4,5-c]pyridine-4(5H)-one, 5-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-1,5,6,7-tetrahydro-4H-pyrazolo[4,3-c]pyridine-4-one, 5-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-1-methyl-1,5,6,7-tetrahydro-4H-pyrazolo[4,3-c]pyridine-4-one, 5-[2-(N-trifluoromethanesulfonyl)aminobenzyl]3-bromo-1-methyl-1,5,6,7-tetrahydro-4H-pyrazolo[4,3-c]pyridine-4-one, 5-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-3-methyl-1-phenyl-1,5,6,7-tetrahydro-4H-pyrazolo[4,3-c]pyridine-4-one, 5-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-3-methyl-1-(pyridine-2-yl)-1,5,6,7-tetrahydro-4H-pyrazolo[4,3-c]pyridine-4-one, 5-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-2-methyl-2,5,6,7-tetrahydro-4H-pyrazolo[4,3-c]pyridine-4-one, 5-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-2,3-dimethyl-2,5,6,7-tetrahydro-4H-pyrazolo[4,3-c]pyridine-4-one, 5-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-3-bromo-2-methyl-2,5,6,7-tetrahydro-4H-pyrazolo[4,3-c]pyridine-4-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-6,7-dihydro-1,7-naphthyridine-8(5H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-3,4-dihydro-2,6naphthyridine-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-2-methyl-7,8-dihydropyrido[4,3-d]pyrimidine-5(6H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-5,6-dihydrothieno[2,3-c]pyridine-7(4H)-one, 5-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-3-bromo-1-methyl-1,5,6,7-tetrahydro-4H-pyrazolo[4,3-c]pyridine-4-one, 5-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-2,3-dimethyl-2,5,6,7-tetrahydro-4H-pyrazolo[4,3-c]pyridine-4-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-6,7-dihydro-1,7-naphthyridine-8(5H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-3,4-dihydro-2,6-naphthyridine-1(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-7,8-dihydro-1,6-naphthyridine-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-dihydroisoquinoline-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-3,3-dimethyl-3,4-dihydroisoquinoline-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]oxazine-4(3H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-2,3-dihydro-4H-benzo[e][1,3]thiadin-4-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-4-methyl-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5,8-difluoro-4-methyl-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5,8-difluoro-4,4-dimethyl-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5,8-difluoro-4-methoxyisoquinoline-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-dihydroisoquinoline-1(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethylsulfonyl)aminobenzyl]-1H-benzo[d][1,2]oxazine-4(3H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethylsulfonyl)aminobenzyl]-5,8-difluoro-4-methyl-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethylsulfonyl)aminobenzyl]-4,4-dimethyl-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethylsulfonyl)aminobenzyl]-isoquinoline-1(2H)-one, N-[2-(N-trifluoromethylsulfonyl)aminophenylethane-1-yl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-difluoromethanesulfonyl)aminobenzyl]-5,8-difluoro-3,4-dihydroisoquinoline-1(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-1,3-dihydroindole-2-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5-fluoro-1,3-dihydroindole-2-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5-chloro-1,3-dihydroindole-2-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-5-bromo-1,3-dihydroindole-2-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-6-chloro-1,3-dihydroindole-2-one, N-[2-(N-trifluoromethanesulfonyl)amino-5-trifluoromethyl-benzyl]-1,3-dihydroindole-2-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-1,3-dihydroindole-2-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-5-fluoro-1,3-dihydroindole-2-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-5-chloro-1,3-dihydroindole-2-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-5-bromo-1,3-dihydroindole-2-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-6-chloro-1,3-dihydroindole-2-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)amino-5-trifluoromethyl-benzyl]-1,3-dihydroindole-2-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-1,4-dihydroisoquinoline-3(2H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-3,4-dihydroquinoline-2(1H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-3-methyl-3,4-dihydroquinazoline-2(1H)-one, N-[2-(N-trifluoromethanesulfonyl)aminobenzyl]-phenanthlysine-6(5H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-1,4-dihydroisoquinoline-3(2H)-one, N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-3,4-dihydroquinoline-2(1H)-one, 1-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-3-methyl-3,4-dihydroquinazoline-2(1H)-one, and N-[2-(N-ethoxycarbonyl-N-trifluoromethanesulfonyl)aminobenzyl]-phenanthlysine-6(5H)-one A compound or salt thereof according to claim 1, selected from the group consisting of the following.

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

9. A composition having herbicidal activity, containing a compound represented by formula [1] or a salt thereof as described in any one of claims 1 to 7, as an active ingredient.

10. A method for weed control comprising treating soil and / or plants with an effective amount of the composition described in claim 9.

11. A method for controlling paddy field weeds, comprising treating paddy field soil with an effective amount of the composition described in claim 9.

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