 Heterocyclic Compound and its use for the control of an arthropod.
专利摘要:
heterocyclic compound and its use for controlling an arthropod plague - the invention relates to a heterocyclic compound represented by formula (1): wherein a ^ 1 ^, a ^ 2 ^, r ^ 1 ^, r ^ 2 ^, r ^ 3 ^, r ^ 4 ^ n, and so on are defined in that description, have an excellent controlling effect on arthropod pests and are useful for controlling arthropod pests. 公开号:BR112012007844B1 申请号:R112012007844-5 申请日:2010-09-30 公开日:2018-03-13 发明作者:Iwakoshi Mitsuhiko 申请人:Sumitomo Chemical Company, Limited； IPC主号:
专利说明:
(54) Title: HETEROCYCLIC COMPOUND AND ITS USE FOR THE CONTROL OF ARTHROPOD PEST. (51) Int.CI .: C07D 417/04; C07D 513/04; A01N 43/78; A01N 43/90; A01P 7/00 (52) CPC: C07D 417/04, C07D 513/04, A01N 43/78, A01N 43/90 (30) Unionist Priority: 07/10/2009 JP 2009-233158 (73) Holder (s) : SUMITOMO CHEMICAL COMPANY, LIMITED (72) Inventor (s): MITSUHIKO IWAKOSHI 1/100 Invention Patent Descriptive Report for HETEROCYCLIC COMPOUND AND ITS USE FOR THE CONTROL OF ARTHROPOD PEST. TECHNICAL FIELD The present invention relates to a certain type of heterocyclic compound and its use for the control of arthropod pests. BACKGROUND OF THE TECHNIQUE GB-A 2,311,010 describes a benzothiazole compound as a production intermediate for medicinal compounds. WO 2006/024642 describes a benzothiazole compound as a production intermediate for dyes. Chem. Pharm. Bull., 30 (8), 2996 (1982) describes a certain type of benzothiazole compound. DESCRIPTION OF THE INVENTION The present invention aims to provide a compound having an excellent control effect on arthropod pests. The present inventors investigated extensively to solve the problem described above, and consequently found that a heterocyclic compound represented by the following formula (1) has an excellent control effect on arthropod pests, leading to the conclusion of the present invention. The present invention is as described below. [1] A heterocyclic compound represented by formula (1): X 1 R 1 R 2 (1) (1), where A 1 and A 2 are the same or different and represent a nitrogen atom or = C (R 5 ) -, R 1 represents a hydrocarbon group of Ci-C6 chain optionally substituted by at least one member selected from Group X, alicyclic hydrocarbon group , C 3 -C 6 -cycloalkyl optionally substituted by at 2/100 minus one selected member from Group X, phenyl group optionally substituted by at least one selected member from Group Y, 5-membered heterocyclic group optionally replaced by at least one selected member from Group Y, 6-membered heterocyclic group optionally substituted by at least one member selected from Group Y, -OR 6 , -S (O) mR 6 , -NR 6 R 7 , -NR 6 C (O) R 9 , -NR 6 CO2R 9 , -C (O) R 10 , -C (NOR 6 ) R w , cyan group, nitro group or halogen atom, R 2 represents a C 1 -C 6 chain hydrocarbon group optionally substituted by at least one member selected from Group X, -CR 6 , -S (O) mR 6 , -NR 6 R 7 , halogen atom or hydrogen atom, R 3 and R 4 are the same or different and represent a C1-C4 chain hydrocarbon group substituted by at least one halogen atom, -OR 11 , -S (O) mR 11 , halogen atom or hydrogen atom (with the condition that R 3 or R 4 represents a C1-C4 chain hydrocarbon group substituted by at least one halogen atom, -OR 11 or -S (O) mR 11 ), alternatively, R 3 and R 4 can be linked to form a 5-membered ring or 6-membered ring replaced by one or more halogen atoms along with the carbon atoms to which R 3 and R 4 are attached, R 5 represents a C1-C3 alkyl group optionally substituted by at least one halogen atom, halogen atom or hydrogen atom, R 6 and R 7 are the same or different and represent a C 1 -C 6 chain hydrocarbon group optionally substituted by at least one member selected from Group X, group C 4 -C 7 cycloalkylmethyl optionally substituted by at least one member selected from Group X, C3-C6 alicyclic hydrocarbon group optionally substituted by at least one member selected from Group X, phenyl group optionally substituted by at least one member selected from Group Y, benzyl group optionally substituted by at least one member selected from Group Y, heterocyclic group of 5 members optionally substituted by at least one member selected from Group Y, heterocyclic group of 6 3/100 members optionally substituted by at least one member selected from Group Y, or hydrogen atom (with the proviso that R 6 does not represent a hydrogen atom when m in -S (O) m R 6 is 1 or 2), R 8 represents a hydrocarbon group of Ci-C6 chain optionally substituted by at least one member selected from Group X, alicyclic hydrocarbon group , C 3 -C 6 -cycloalkyl optionally substituted by at least one member selected from Group X, or phenyl group optionally substituted by at least one selected member of Group Y, R 9 represents a C1-C4 alkyl group optionally substituted by at least one halogen atom, R 10 represents a C1-C4 alkyl group optionally substituted by at least one halogen atom, or hydrogen atom, R 11 represents a C 1 -C 4 hydrocarbon group substituted by at least one halogen atom, m represents 0, 1 or 2, and n represents 0 or 1. Group X; the group consisting of C 1 -C 4 alkoxy groups optionally substituted by at least one halogen atom, and halogen atoms. Group Y: the group consisting of C 1 -C 4 alkyl groups optionally substituted by at least one halogen atom, C 1 -C 4 alkoxy groups optionally substituted by at least one halogen atom, cyano group, nitro group and halogen atoms ( hereinafter referred to as the present compound). [2] The heterocyclic compound according to [1], where R 5 is a hydrogen atom. [3] The heterocyclic compound according to [1] or [2], where R 2 is a hydrogen atom. [4] The heterocyclic compound according to any one of [1] to [3], where R 1 is a C 1 -C 6 chain hydrocarbon group optionally substituted by at least one member selected from Group X, -OR 6 , - S (O) mR 6 , -NR 6 R 7 , -NR 6 C (O) R 8 , -NR 6 CO 2 R 9 , -C (O) R 10 , -C (NOR 6 ) R 10 , cyan group , nitro group or halogen atom, 4/100 R 6 and R 7 are the same or different and are a Ci-C6 chain hydrocarbon group optionally substituted by at least one member selected from Group X, or hydrogen atom (with the proviso that R 6 is a Ci chain hydrocarbon group) -C6 optionally subs5 substituted by at least one selected member of Group X when m in -S (O) m R 6 is 1 or 2), and R 6 is a C- | -C 6 chain hydrocarbon group optionally substituted by at least one member selected from Group X. [5] The heterocyclic compound according to [4], wherein R 1 is a C1-C6 chain hydrocarbon group optionally substituted by at least one member selected from Group X, -OR 6 , -S (O) m R 6 , -NR 6 R 7 or halogen atom, R 6 is a CrCô chain hydrocarbon group optionally substituted by at least one member selected from Group X, and '15 R 7 is a C / -C6 chain hydrocarbon group optionally substituted by at least one member selected from Group X, or atom hydrogen, [6] An arthropod plague control composition comprising the heterocyclic compound as described in any one of [1] to [5], and an inert vehicle. [7] An arthropod plague control method comprising applying an effective amount of the heterocyclic compound as described in any one of [1] to [5] to arthropod pests or areas where arthropod pests live. [8] Use of the heterocyclic compound as described in any one of [1] to [5] for the control of arthropod pests. The present compound has a control effect on arthropod pests. MODE OF CARRYING OUT THE INVENTION The substituents used in the descriptions of this specification will be illustrated with examples mentioned below. In this specification, for example, C4-C7 in the C4-C7 cycloalkylmethyl group 5/100 means that the number of carbon atoms that make up the entire cycloalkylmethyl group is in the range of 4 to 7. Halogen atom in the present compound means a fluorine atom, chlorine atom, bromine atom and iodine atom. Ci-C6 chain hydrocarbon group Examples optionally substituted by at least one member selected from the X group represented by R 1 include C-group C 6 alkyl such as methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, sec-butyl group, tert-butyl group, pentyl group, 2,2-dimethylpropyl group, 3-methylbutyl group, 2,3-dimethylbutyl group, 3,3-dimethylbutyl group and hexyl group; C 1 -C 6 alkyl groups substituted by at least one member selected from Group X such as a methoxymethyl group, ethoxymethyl group, 1-methoxyethyl group and trifluoromethyl group; C2-C 6 alkenyl groups such as a vinyl group, 1propenyl group, 2-propenyl group, isopropenyl group, 2-methyl-1-propenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, group 1- pentenyl and 1-hexenyl group; C 2 -C 6 alkenyl groups substituted by at least one member selected from Group X such as a 3,3-difluoro-2-propenyl group and 3-methoxy-1-propenyl group; C 2 -C 6 alkynyl groups such as an ethynyl group, propargyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 3,3-dimethyl-1butynyl group, 1-pentinyl group and 1-hexynyl group; and C 2 -C 6 alkynyl groups substituted by at least one member selected from Group X such as a 3-methoxy-1-propynyl group. Examples of C 3 -C 5 alicyclic hydrocarbon group optionally substituted by at least one member selected from Group X represented by R 1 include a cyclopropyl group, cyclobutyl group, cyclopentyl group and cyclohexyl group. Examples of phenyl group optionally substituted by at least one member selected from Group Y represented by R 1 include a phenyl group, 2-chlorophenyl group, 3-chlorophenyl group, 4-chlorophenyl group, 6/100 2-methylphenyl group, 3-methylphenyl group, 4-methylphenyl group, 2-methoxyphenyl group, 3-methoxyphenyl group, 4-methoxyphenyl group, group 2- (trifluoromethyl) phenyl, group 3- (trifluoromethyl) phenyl, group 4- (trifluoromethyl) phenyl, group 2- nitrophenyl, 3-nitrophenyl group, 4-nitrophenyl group, 2-cyanophenyl group, 3-cyanophenyl group and 4-cyanophenyl group. Examples of a 5-membered heterocyclic group optionally substituted by at least one member selected from the Group represented by F include 5-membered saturated heterocyclic groups such as a pyrrolidin-1-yl group and others; and 5-membered aromatic heterocyclic groups such as a pyrazol-1-yl group, 3-chloropyrazol-1-yl group, 3bromopyrazol-1-yl group, 3-nitropyrazol-1-yl group, 3-methylpyraz1-1-yl group , 3- (trifluoromethyl) pyrazol-1-yl group, 4-methylpyrazol-1-yl group, 4-chloropyrazol-1-yl group, 4-bromopyrazol-1-yl group, 4-cyanopyrazol-1-yl group, group imidazol-1-yl, group 4- (trifluoromethyl) imidazol-1-yl, pyrrole-1-yl group, 1,2,4-triazol-1-yl group, 3-chloro-1,2,4-triazole group -1-yl, 1,2,3,4-tetrazol-1-yl group, 1,2,3,5-tetrazol-1-yl group, 2-furyl group, 3-furyl group, 2-thienyl group and 3-thienyl group. 6-membered heterocyclic group optionally substituted by at least one member selected from Group Y represented by R 1 includes 6-membered saturated heterocyclic groups such as a piperidyl group, morpholino group, thiomorpholine group and 4-methylpiperazin-1-yl group and others; and 6-membered aromatic heterocyclic groups such as a 2-pyridyl group, 3-pyridyl group and 4-pyridyl group. Examples of the hydrocarbon group of the CrC 6 chain optionally substituted by at least one member selected from Group X represented by R 2 include a CrCe alkyl group such as a methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, sec group -butyl, tert-butyl group, pentyl group, 2,2-dimethylpropyl group, group 3-methylbutyl, 2,3-dimethylbutyl group, 3,3-dimethylbutyl group and hexyl group; C1-C6 alkyl groups substituted by at least one member selected from Group X such as a methoxymethyl group, ethoxymethyl group, 1-methoxyethyl group and trifluoromethyl group; 7/100 C 2 -C 6 alkenyl groups such as a vinyl group, 1-propenyl group, 2-propenyl group, isopropenyl group, 2-methyl-1-propenyl group, 1-butenyl group, 2-butenyl group, group 3 -butenyl, group 1-pentenyl and group 1-hexenyl and others; C 2 -C 6 alkenyl groups substituted by at least one member selected from Group X such as a 3,3-difluoro-2-propenyl group and 3-methoxy-1-propenyl group; C 2 -C 6 alkynyl groups such as an ethynyl group, propargyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 3,3-dimethyl-1butynyl group, 1-pentynyl group and 1-hexynyl group: e C 2 -C 6 alkynyl groups substituted by at least one member selected from Group X such as a 3-methoxy-1-propynyl group. Examples of the CL-C4 chain hydrocarbon group substituted by at least one halogen atom represented by R 3 or R 4 include a trifluoromethyl group, 1,1-difluoroethyl group, 2,2,2-trifluoroethyl group, pentafluoroethyl group and heptafluoroisopropyl group . Examples of a C1-C4 alkyl group optionally substituted by at least one halogen atom represented by R 5 include a methyl group, ethyl group, propyl group, isopropyl group and trifluoromethyl group. Examples of a C 1 -C 6 chain hydrocarbon group optionally substituted by at least one member selected from Group X represented by R 6 or R 7 include C 1 -C 6 alkyl groups such as a methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, sec-butyl group, tert-butyl group, 1-methylbutyl group, 2-methylbutyl group, 3-methylbutyl group, 1-ethylpropyl group, 1,2-dimethylpropyl group, 2,2-dimethylpropyl group, pentyl group , 1,2-dimethylbutyl group, 2,2-dimethylbutyl group, 1,3-dimethylbutyl group, 1-methylpentyl group, 2-methylpentyl group, 3-methylpentyl group, 4-methylpentyl group and hexyl group; CiC 6 alkyl groups substituted by at least one member selected from Group X such as a 2-methoxyethyl group, 2-ethoxyethyl group, difluoromethyl group, trifluoromethyl group, 2,2-difluoroethyl group, 2,2,2-trifluoroethyl group, group 2,2,2-trichloroethyl, 1-methyl-2,2,2-trifluoroethyl group, 8/100 1-methyl-2,2,2-trichloroethyl group, 1,1,2,2-tetrafluoroethyl group, 2,2-difluoropropyl group and 2,2,3,3-tetrafluoropropyl group; C 3 -C 6 alkenyl groups such as a 2-propenyl group, 1-methyl-2-propenyl group, 2-methyl-2-propenyl group, 2-butenyl group, 3-butenyl group, 1-methyl-2-butenyl group and 1-methyl-3-butenyl group; C 3 -C 6 alkenyl groups substituted by at least one member selected from Group X such as a 3,3-dichloro-2-propenyl group, 3,3-difluoro-2-propenyl group; and C 3 -C 6 alkynyl groups optionally substituted by at least one member selected from Group X such as a propargyl group, 1- methyl-2-propynyl, 2-butynyl group, 1-methyl-2-butynyl group and 1-methyl3-butynyl group. Examples of the C 4 -C 7 cycloalkylmethyl group represented by R 6 or R 7 include a cyclopropylmethyl group, cyclobutylmethyl group, cyclopentylmethyl group and cyclohexylmethyl group. Examples of the C 3 -C 6 alicyclic hydrocarbon group represented by R 6 or R 7 include a cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group and 2-cyclohexenyl group. Examples of phenyl group optionally substituted by at least one member selected from Group Y represented by R 6 or R 7 include a phenyl group, 2-chlorophenyl group, 3-chlorophenyl group, 4 chlorophenyl group, 2-methylphenyl group, 3-methylphenyl group, 4-methylphenyl group, group 2- methoxyphenyl, group 3-methoxyphenyl, group 4-methoxyphenyl, group 2- (trifluoromethyl) phenyl, group 3- (trifluoromethyl) phenyl, group 4- (trifluoromethyl) phenyl, group 2-cyanophenyl, group 3-cyanophenyl, group 4 -cyanophenyl, 2nitrophenyl group, 3-nitrophenyl group and 4-nitrophenyl group. Examples of a benzyl group optionally substituted by at least one member selected from Group Y represented by R® or R 7 include a benzyl group, 2-chlorobenzyl group, 3-chlorobenzyl group, 4 chlorobenzyl group, 2-methylbenzyl group, 3-methylbenzyl group, 4-methylbenzyl group, 2-methoxybenzyl group, 3-methoxybenzyl group and 4-methoxybenzyl group. 9/100 Examples of a 5-membered heterocyclic group represented by R 6 or R 7 include aromatic 5-membered heterocyclic groups such as a 2-thiazolyl group, 2-thienyl group and 3-thienyl group. Examples of the 6-membered heterocyclic group represented by R 6 or R 7 include 6-membered aromatic heterocyclic groups such as a 2-pyridyl group, 3-pyridyl group, 4-pyridyl group, 2-pyrimidinyl group and 4-pyrimidinyl group. Examples of a C 1 -C 6 chain hydrocarbon group optionally substituted by at least one member selected from Group X represented by R 8 include C 1 -C 6 alkyl groups such as a methyl group, ethyl group, propyl group, isopropyl group, butyl group, group isobutyl, sec-butyl group, tert-butyl group, 1-methylbutyl group, 1-ethylpropyl group, pentyl group and hexyl group; Ci-C 6 alkyl groups substituted by at least one member selected from Group X such as a metoximetila group difluorometila group, trifluoromethyl group, triclorometila group pentafluoroetila group and 1,1,2,2-tetrafluoroetila; C2-C 6 alkenyl groups optionally substituted by at least one member selected from Group X such as a vinyl group, 1propenyl group, 2-propenyl group, isopropenyl group, 2,2-dimethylethyl group, 1-butenyl group, 2-butenyl group and 3,3,3-trifluoro-1-propenyl group; and C 2 -C 6 alkynyl groups optionally substituted by at least one member selected from Group X such as a propargyl group, group 1-propynyl and group 3,3,3-trifluoro-1-propynyl. Examples of the C 3 -C 6 alicyclic hydrocarbon group represented by R 8 include a cyclopropyl group, cyclobutyl group, cyclopentyl group and cyclohexyl group. Examples of phenyl group optionally substituted by at least one member selected from Group Y represented by R 8 include a phenyl group, 2-chlorophenyl group, 3-chlorophenyl group, 4-chlorophenyl group, 2-methylphenyl group, 3-methylphenyl group, group 4-methylphenyl, 2-methoxyphenyl group, 3-methoxyphenyl group, 4-methoxyphenyl group, group 2- (trifluoromethyl) 10/100 phenyl, group 3- (trifluoromethyl) phenyl, group 4- (trifluoromethyl) phenyl, group 2-cyanophenyl, group 3-cyanophenyl, group 4-cyanophenyl, group 2-nitrophenyl, group 3-nitrophenyl and 4-nitrophenyl group. Examples of a C1-C4 alkyl group optionally substituted by at least one halogen atom represented by R 9 include a methyl group, ethyl group, 2,2,2-trifluoroethyl group, propyl group, isopropyl group, butyl group, isobutyl group, group sec-butyl and tert-butyl group. Examples of the C1-C4 alkyl group optionally substituted by at least one halogen atom represented by R 10 include a methyl group, trifluoromethyl group, trichloromethyl group, ethyl group, 2,2,2-trifluoroethyl group, pentafluoroethyl group, propyl group, group isopropyl, butyl group, isobutyl group, sec-butyl group and tert-butyl group. Examples hydrocarbon group of Ci-C 4 chain substituted by at least one halogen atom represented by R 11 include trifluoromethyl group, difluorometila group and 2,2,2-trifluoroetila. Examples of the present compound include the following compounds. Compounds of formula (1) in which R 5 represents a hydrogen atom; Compounds of formula (1) in which R 2 represents a halogen atom or hydrogen atom; Compounds of formula (1) in which R 2 represents a hydrogen atom; Compounds of formula (1) where R 1 represents a C 3 -C 6 alicyclic hydrocarbon group optionally substituted by at least one member selected from Group X, phenyl group optionally substituted by at least one member selected from Group 1, 5 membered heterocyclic group optionally substituted by at least one member selected from Group Y, or a 6-membered heterocyclic group optionally substituted by at least one member selected from Group Y; Compounds of formula (1) in which R 1 represents a C 1 -C 6 chain hydrocarbon group optionally substituted by at least one member selected from Group X, -OR 6 , -S (O) mR 6 , -NR 6 R 7 , - NR 6 C (O) R 8 -, 11/100 NR 6 CC> 2R 9 , -C (O) R 10 , -C (NOR 6 ) R 10 , cyano group, nitro group or halogen atom, R 6 and R 7 are the same or different and represent a hydrocarbon group of Ci-C6 chain optionally substituted by at least one member selected from Group X, or hydrogen atom (with the condition that if m in -S (O) mR 6 is 1 or 2, then R 5 represents a chain hydrocarbon group Ci-C6 optionally substituted by at least one member selected from Group X), R 8 represents a C1-C6 chain hydrocarbon group optionally substituted by at least one member selected from Group X; Compounds of formula (1) where R 1 represents a C 1 -C 6 chain hydrocarbon group optionally substituted by at least one member selected from Group X, -OR 6 , -S (O) mR 6 , -NR 6 R 7 or atom halogen, R 6 represents a C 1 -C 6 chain hydrocarbon group optionally substituted by at least one member selected from Group X, R 7 represents a C 1 -C 6 chain hydrocarbon group optionally substituted by at least one selected member from Group X or atom hydrogen; Compounds of formula (1) in which R 1 represents a C1-C6 chain hydrocarbon group optionally substituted by at least one member selected from Group X, -OR 6 , -S (O) mR 6 or halogen atom, R 6 represents a C1-C6 chain hydrocarbon group optionally substituted by at least one member selected from Group X; Compounds of formula (1) in which R 1 represents -OR 6 , -S (O) mR 6 or halogen atom, R 6 represents C 1 -C 6 chain hydrocarbon group optionally substituted by at least one member selected from Group X; Compounds of formula (1) wherein R 3 or R 4 represents a C1-C4 chain hydrocarbon group substituted by at least one halogen atom, -OR 11 or S (O) m R 11 ; Compounds of formula (1) where R 3 or R 4 represents a C1-C4 chain hydrocarbon group substituted by at least one fluorine atom, -OR 11 or -S (O) m R 11 , R 11 represents a group of hydrocarbon 12/100 C1-C4 chain replaced by at least one fluorine atom; Compounds of formula (1) in which R 3 or R 4 represent a trifluoromethyl group, -OR 11 or -S (O) m R 11 , R 11 represents a trifluoromethyl group; Compounds of formula (1) in which R 3 represents a C- | -C 4 chain hydrocarbon group substituted by at least one halogen atom, or -OR 11 ; Compounds of formula (1) wherein R 4 represents a C1-C4 chain hydrocarbon group substituted by at least one halogen atom, or -OR 11 ; Compounds of formula (1) in which R 3 represents a C1-C4 chain hydrocarbon group substituted by at least one halogen atom; Compounds of formula (1) where R 3 represents a C1-C4 chain hydrocarbon group substituted by at least one fluorine atom; Compounds of formula (1) in which R 3 represents a trifluoromethyl group; Compounds of formula (1) wherein R 4 represents a C1-C4 chain hydrocarbon group substituted by at least one halogen atom; Compounds of formula (1) wherein R 4 represents a C1-C4 chain hydrocarbon group substituted by at least one fluorine atom; Compounds of formula (1) in which R 4 represents a trifluoromethyl group; Compounds of formula (1) where R 3 represents -OR 11 ; Compounds of formula (1) in which R 3 represents -OR 11 , R 11 represents a C1-C4 chain hydrocarbon group substituted by at least one fluorine atom; Compounds of formula (1) in which R 3 represents -OR 11 , R 11 represents a trifluoromethyl group; Compounds of formula (1) where R 4 represents -OR 11 ; Compounds of formula (1) in which R 4 represents -OR 11 , R 11 re13 / 100 has a C1-C4 chain hydrocarbon group substituted by at least one fluorine atom; Compounds of formula (1) in which R 4 represents -OR 11 , R 11 represents a trifluoromethyl group; Compounds of formula (1) where R 3 represents a C1-C4 chain hydrocarbon group substituted by at least one halogen atom, R 4 represents a hydrogen atom; Compounds of formula (1) in which R 3 represents -OR 11 , R 11 represents a CtC 4 hydrocarbon group substituted by at least one fluorine atom, R 4 represents a hydrogen atom; Compounds of formula (1) in which R 3 represents a C 1 -C 4 hydrocarbon group substituted by at least one fluorine atom, R 4 represents a hydrogen atom; Compounds of formula (1) in which R 3 represents a hydrogen atom, R 4 represents a C 1 -C 4 hydrocarbon group substituted by at least one halogen atom; Compounds of formula (1) in which R 3 represents a hydrogen atom, R 4 represents a C 1 -C 4 chain hydrocarbon group substituted by at least one fluorine atom; Compounds of formula (1) in which R 3 represents a hydrogen atom, R 4 represents -OR 11 , R 11 represents a C 1 -C 4 hydrocarbon group substituted by at least one fluorine atom; Compounds of formula (1) in which R 3 represents a trifluoromethyl group, R 4 represents a hydrogen atom; Compounds of formula (1) in which R 3 represents -OR 11 , R 11 represents a trifluoromethyl group, R 4 represents a hydrogen atom; Compounds of formula (1) in which R 3 represents a hydrogen atom, R 4 represents a trifluoromethyl group; Compounds of formula (1) in which R 3 represents a hydrogen atom, R 4 represents -OR 11 , R 11 represents a trifluoromethyl group; Compounds of formula (1) where A 1 represents = C (R 5 ) -, A 2 represents a nitrogen atom or = C (R 5 ) -; 14/100 Compounds of formula (1) where A 1 represents = C (R 5 ) -1, A 2 represents a nitrogen atom or = C (R 5 ) -, R 5 represents a hydrogen atom; Compounds of formula (1) where A 1 represents a nitrogen atom, A 2 represents = C (R 5 ) -, R 5 represents a hydrogen atom; Compounds of formula (1) where A 1 represents = C (R 5 ) -, A 2 represents a nitrogen atom, R 5 represents a hydrogen atom; Compounds of formula (1) where A 1 and A 2 represent = C (R 5 ) -, R 5 represents a hydrogen atom; Compounds of formula (1) in which R 1 represents a CvC4 alkyl group optionally substituted by at least one halogen atom, C2-C4 alkenyl group, pyrrolidyl group, piperidyl group, morpholino group, imidazolyl group, pyrazolyl group, triazolyl group, group pyrazolyl substituted by at least one C1-C3 alkyl group, pyrazolyl group substituted by at least one (C1-C3 alkyl group substituted by at least one halogen atom), phenyl group, pyridyl group, -OR 6a (R 6a represents a group C1-C4 alkyl optionally substituted by at least one halogen atom, C3-C4 alkenyl group optionally substituted by at least one halogen atom, C3-C4 alkynyl group, benzyl group or C4-C7 cycloalkylmethyl group), -S (O) m R 6b (R 6b represents a C1-C4 alkyl group optionally substituted by at least one halogen atom, m represents 0, 1 or 2), -NR 6c R 7a (R 6c and R 7a are the same or different and represent a C1-C4 alkyl group optionally sub substituted by at least one halogen atom, or hydrogen atom), -NHC (O) R 8 or halogen atom, R 2 represents a halogen atom or hydrogen atom, R 8 represents an optionally substituted C1-C4 alkyl group at least one halogen atom; Compounds of formula (1) where R 1 represents a C1-C4 group optionally substituted by at least one halogen atom, C2-C4 alkenyl group, pyrrolidyl group, piperidyl group, morpholino group, imidazolyl group, pyrazolyl group, triazolyl group, pyrazolyl group substituted by at least one C1-C3 alkyl group, pyrazolyl group substituted by at me15 / 100 in one (C1-C3 alkyl group substituted by at least one halogen atom), phenyl group, pyridyl group, -OR 6a (R 6a represents a C1-C4 alkyl group optionally substituted by at least one halogen atom, C3-C4 alkenyl group optionally substituted by at least one halogen atom, C3-C4 alkynyl group, benzyl group or C4-C7 cycloalkylmethyl group), - S (O) m R 6b (R 6b represents C / -C4 alkyl group optionally substituted by at least one halogen atom, m represents 0, 1 or 2), -NR 6c R 7a (R 6c and R 7a are the same or different and represent an optionally substituted C1-C4 alkyl group substituted by at least one halogen atom, or hydrogen atom), -NHC (O) R 8 or halogen atom, R 2 represents a hydrogen atom, R 5 represents a hydrogen atom, R 8 represents a C1- group C4 alkyl optionally substituted by at least one halogen atom; Compounds of formula (1) in which R 1 represents a C1-C4 alkyl group optionally substituted by at least one halogen atom, C2-C4 alkenyl group, pyrrolidyl group, piperidyl group, morpholino group, imidazolyl group, pyrazolyl group, triazolyl group , pyrazolyl group substituted by at least one C1-C4 alkyl group, pyrazolyl group substituted by at least one (C1 -C3 alkyl group substituted by at least one halogen atom), phenyl group, pyridyl group, -OR 6a (R 6a represents a C1-C4 alkyl group optionally substituted by at least one halogen atom, C3-C4 alkenyl group optionally substituted by at least one halogen atom, C3-C4 alkynyl group, benzyl group or C4-C7 cycloalkylmethyl group), - S (O) mR 6b (R 6b represents a C1-C4 alkyl group optionally substituted by at least one halogen atom, m represents 0, 1 or 2), -NR 6c R 7a (R 6c and R 7a are the same or different and represent an optional C1-C4 alkyl group substituted by at least one halogen atom, or hydrogen atom), -NHC (O) R 8 or halogen atom, R 2 represents a hydrogen atom, R 3 represents a C1-C4 chain hydrocarbon group replaced by minus a halogen atom, or -OR 11 , R 4 represents a hydrogen atom, R 5 represents a hydrogen atom, R 8 represents an optionally substituted C1-C4 alkyl group 16/100 for at least one halogen atom; Compounds of formula (1) in which R 1 represents a C1-C4 alkyl group optionally substituted by at least one halogen atom, C2-C4 alkenyl group, pyrrolidyl group, piperidyl group, morpholino group, imidazolyl group, pyrazolyl group, triazolyl group , pyrazolyl group substituted by at least one C-1-C3 alkyl group, pyrazolyl group substituted by at least one (C1-C3 alkyl group substituted by at least one halogen atom), phenyl group, pyridyl group, -OR 6a (OR 6a represents a C1-C4 alkyl group optionally substituted by at least one halogen atom, C3-C4 alkenyl group optionally substituted by at least one halogen atom, C3-C4 alkynyl group, benzyl group or C4-C7 cycloalkylmethyl group), - S (O) m R 6b (R 6b represents a C1-C4 alkyl group optionally substituted by at least one halogen atom, m represents 0, 1 or 2), -NR 6c R 7a (R 6c and R 7a are the same or different and represent an optionally C1-C4 alkyl group substituted by at least one halogen atom, or hydrogen atom), -NHC (O) R 8 or halogen atom, R 2 represents a hydrogen atom, R 3 represents a C1-C4 chain hydrocarbon group replaced by at least a halogen atom, R 4 represents a hydrogen atom, R 5 represents a hydrogen atom, R 8 represents a C1-C4 alkyl group optionally substituted by at least one halogen atom; Compounds of formula (1) in which R 1 represents a C1-C4 alkyl group optionally substituted by at least one halogen atom, C2-C4 alkenyl group, pyrrolidyl group, piperidyl group, morpholino group, imidazolyl group, pyrazolyl group, triazolyl group , pyrazolyl group substituted by at least one C1-C3 alkyl group, pyrazolyl group substituted by at least one (C1-C3 alkyl group substituted by at least one halogen atom), phenyl group, pyridyl group, -OR 6a (R 6a represents a C1-C4 alkyl group optionally substituted by at least one halogen atom, C3-C4 alkenyl group optionally substituted by at least one halogen atom, C3-C4 alkynyl group, benzyl group or C4-C7 cycloalkylmethyl group), -S ( O) m R 6b (R 6b represents an optional C1-C4 alkyl group 17/100 finally substituted by at least one halogen atom, m represents 0, 1 or 2), -NR 6c R 7a (R 6c and R 7a are the same or different and represent an optionally C1-C4 alkyl group between replaced by at least one halogen atom, or hydrogen atom), -NHC (O) R 8 or halogen atom, R 2 represents a hydrogen atom, R 3 represents a trifluoromethyl group, R 4 represents a hydrogen atom , R 5 represents a hydrogen atom, R 8 represents a C 1 -C 4 alkyl group optionally substituted by at least one halogen atom; Compounds of formula (1) in which R 1 represents a C 1 -C 4 alkyl group optionally substituted by at least one halogen atom, OR 6a (R 6a represents a C 1 -C 4 alkyl group optionally substituted by at least one halogen atom), -S (O) mR 6a (m represents 0, 1 or 2), NR 6b R 7a (R 6b and R 7a are the same or different and represent a C-iC 4 alkyl group optionally substituted by at least one halogen atom , or hydrogen atom), or halogen atom; Compounds of formula (1) in which R 1 represents a C 1 -C 4 alkyl group optionally substituted by at least one halogen atom, OR 6a (R 6a represents a C 1 -C 4 alkyl group optionally substituted by at least one halogen atom), -S (O) m R 6a (m represents 0, 1 or 2), NR 6b R 7a (R 6b and R 7a are the same or different and represent a C 1 -C 4 alkyl group optionally substituted by at least one halogen atom , or hydrogen atom), or halogen atom, R 2 represents a halogen atom or hydrogen atom; Compounds of formula (1) in which R 1 represents a C 1 -C 4 alkyl group optionally substituted by at least one halogen atom, OR 6a (R 6a represents a C 1 -C 4 alkyl group optionally substituted by at least one halogen atom), -S (O) m R 6b (m represents 0, 1 or 2), NR 6b R 7a (R 6b and R 7a are the same or different and represent a C1-C4 alkyl group optionally substituted by at least one halogen atom , or hydrogen atom), or halogen atom, R 2 represents a hydrogen atom, R 5 represents a hydrogen atom; Compounds of formula (1) in which R 1 represents a C 1 -C 4 group 18/100 alkyl optionally substituted by at least one halogen atom, OR 6a (R 6a represents a C1-C4 alkyl group optionally substituted by at least one halogen atom), -S (O) mR 6a (m represents 0, 1 or 2), NR 6b R 7a (R 6b and R 7a are the same or different and represent a C1-C4 alkyl group optionally substituted by at least one halogen atom, or hydrogen atom), or halogen atom, R 2 represents a hydrogen atom, R 3 represents a C1C4 chain hydrocarbon group substituted by at least one halogen atom, or -OR 11 , R 4 represents a hydrogen atom, R 5 represents a hydrogen atom; Compounds of formula (1) where R 1 represents a C1-C4 alkyl group optionally substituted by at least one halogen atom, OR 6a represents a C1-C4 alkyl group optionally substituted by at least one halogen atom), -S ( O) mR 6a (m represents 0, 1 or 2), NR 6b R 7a (R 6b and R 7a are the same or different and represent a C1-C4 alkyl group optionally substituted by at least one halogen atom, or hydrogen), or halogen atom, R 2 represents a hydrogen atom, R 3 represents a C1C4 chain hydrocarbon group substituted by at least one halogen atom, R 4 represents a hydrogen atom, R 5 represents a hydrogen atom; Compounds of formula (1) in which R 1 represents a C1-C4 alkyl group optionally substituted by at least one halogen atom, OR 6a (R 6a represents a C1-C4 alkyl group optionally substituted by at least one halogen atom), -S (O) m R 6a (m represents 0, 1 or 2), NR 6b R 7a (R 6b θ R 7a are the same or different and represent a C1-C4 alkyl group optionally substituted by at least one halogen atom , or hydrogen atom), or halogen atom, R 2 represents a hydrogen atom, R 3 represents a hydrogen atom, R 4 represents a C1-C4 chain hydrocarbon group substituted by at least one halogen atom, or - OR 11 , R 5 represents a hydrogen atom; Compounds of formula (1) in which R 1 represents a Ο ^ 4 alkyl group optionally substituted by at least one halogen atom, OR 6a (R 6a represents a C1-C4 alkyl group optionally substituted by 19/100 at least one halogen atom), -S (O) m R 6a (m represents 0, 1 or 2), NR 6b R 7a (R 6b and R 7a are the same or different and represent a C1- group C4 alkyl optionally substituted by at least one halogen atom, or hydrogen atom), or halogen atom, R 2 represents a hydrogen atom, R 3 represents a hydrogen atom, R 4 represents a C1-C4 chain hydrocarbon group replaced by at least one halogen atom, R 5 represents a hydrogen atom; Compounds of formula (1) in which R 1 represents a C1-C4 alkyl group optionally substituted by at least one halogen atom, OR 6a (R 6a represents a C1-C4 alkyl group optionally substituted by at least one halogen atom), -S (O) mR 6a (m represents 0, 1 or 2), NR 6b R 7a (R 6b and R 7a are the same or different and represent a C1-C4 alkyl group optionally substituted by at least one halogen atom, or hydrogen atom), or halogen atom, R 2 represents a hydrogen atom, R 3 represents a C1C4 chain hydrocarbon group substituted by at least one fluorine atom, R 4 represents a hydrogen atom, R 5 represents an atom hydrogen; Compounds of formula (1) in which R 1 represents a C1-C4 alkyl group optionally substituted by at least one halogen atom, -OR 6a (R 6a represents a C1-C4 alkyl group optionally substituted by at least one halogen atom ), -S (O) m R 6a (m represents 0, 1 or 2), -NR 6b R 7a (R eb and R 7a are the same or different and represent a C1-C4 alkyl group optionally substituted by at least one halogen atom, or hydrogen atom), or halogen atom, R 2 represents a hydrogen atom, R 3 represents a trifluoromethyl group, R 4 represents a hydrogen atom, R 6 represents a hydrogen atom; Compounds of formula (1) in which A 1 represents = C (R 5 ) -, A 2 represents a nitrogen atom or = C (R 5 ) -, R 1 represents a C1C4 alkyl group optionally substituted by at least one atom halogen, -OR 6a (R 6a represents a C1-C4 alkyl group optionally substituted by at least one halogen atom), -S (O) mR 6a (m represents 0, 1 or 2), -NR 6b R 7a ( R 6b and R 7a are the same or different and represent a gru20 / 100 po C1-C4 alkyl optionally substituted by at least one halogen atom, or hydrogen atom) or halogen atom, R 2 represents a hydrogen atom, R 3 represents trifluoromethyl group, R 4 represents a hydrogen atom, R 5 represents a hydrogen atom; Compounds of formula (1) in which R 1 represents a C1-C4 alkyl group optionally substituted by at least one halogen atom, OR 6 , -S (O) mR 6 (m represents 0, 1 or 2) or halogen atom , R 2 represents a hydrogen atom, R 3 represents a trifluoromethyl group, R 4 represents a hydrogen atom, R 5 represents a hydrogen atom, R 6 represents a CrC4 alkyl group optionally substituted by at least one halogen atom; Compounds of formula (1) where A 1 represents = C (R 5 ) -, A 2 represents a nitrogen atom or = C (R 5 ) -, R 1 represents a C 1 C 4 alkyl group optionally substituted by at least one atom of halogen, -OR 6 , -S (O) mR 6 (m represents 0, 1 or 2) or halogen atom, R 2 represents a hydrogen atom, R 3 represents a trifluoromethyl group, R 4 represents a hydrogen atom, R 5 represents a hydrogen atom, R 6 represents a C 1 -C 4 alkyl group optionally substituted by at least one halogen atom; Compounds of formula (1) where A 1 represents = C (R 5 ) -, A 2 represents a nitrogen atom or = C (R 5 ) -, R 1 represents an OR 6 , S (O) mR 6 (m represents 0, 1 or 2) or halogen atom, R 2 represents a hydrogen atom, R 3 represents a trifluoromethyl group, R 4 represents a hydrogen atom, R 5 represents a hydrogen atom, R 6 represents a CrC 4 group alkyl optionally substituted by at least one halogen atom. The method of producing the present compound will be described. The present compound can be produced, for example, by Production Method 1 to Production Method 6 below. PRODUCTION METHOD 1 A compound (4) which is a compound represented by formula (1) in which n is 0 can be produced by reacting a compound (2) and a com21 / 100 post (3). [where, R 1 , R 2 , R 3 , R 4 , A 1 and A 2 represent the same meanings as described above]. The reaction is usually carried out in the presence of a solvent. Examples of the solvent to be used in the reaction include sulfoxides such as dimethyl sulfoxide (hereinafter, referred to as DMSO), aromatic hydrocarbons such as nitrobenzene, and mixtures of these In the reaction, the compound (3) is usually used in a proportion of 0.5 to 3 mois with respect to 1 mole of the compound (2). The reaction temperature of the reaction is usually in the range of 50 to 200 ° C. The reaction time of the reaction is usually in the range of 0.1 to 24 hours. After completion of the reaction, water is added to the reaction mixture, then the mixture is extracted with an organic solvent, and the organic layer is subjected to post-treatment operations such as drying and concentration, thus, the compound (4) can be isolated. The isolated compound (4) can also be purified by chromatography, recrystallization and others. PRODUCTION METHOD 2 A compound (4-b) which is a compound represented by formula (1) where n represents 0 and R 1 represents -OR 6x can be produced by reacting a compound (4-a) and a compound (5) in the presence of a base. + R ex OH (5) (4-b) where, R 2 , R 3 , R 4 , A 1 and A 2 represent the same meanings as described above, R 6x represents an optionally substituted CiC 6 chain hydrocarbon group 22/100 with at least one member selected from Group x, group C4-C7 cycloalkylmethyl optionally substituted by at least one member selected from Group X, alicyclic hydrocarbon group C 3 -C 6 optionally substituted by at least one member selected from Group X, phenyl group optionally substituted by at least one member selected from Group Y, benzyl group optionally substituted by at least one member selected from Group Y, 5-membered heterocyclic group optionally substituted by at least one member selected from Group Y or 6-membered heterocyclic group optionally substituted by at least one member selected from Group Y]. The reaction can be carried out in the presence of a solvent. A solvent amount of the compound (5) is used in some cases. Examples of the solvent to be used in the reaction include ethers such as tetrahydrofuran (hereinafter referred to as THF), ethylene glycol dimethyl ether and 1,4-dioxane, aromatic hydrocarbons such as toluene and xylene, nitriles such as acetonitrile, amides of acid such as N, Ndimethylformamide (hereinafter referred to as DMF), sulfoxides such as DMSO, and mixtures thereof. Examples of the base to be used in the reaction include alkali metal hydrides such as sodium hydride, and carbonates such as potassium carbonate, etc. In the reaction, the compound (5) is usually used in a proportion of 1 to 100 moles with respect to 1 mole of the compound (4-a), and the base is usually used in a ratio of 1 to 10 moles with respect to 1 mole of compound (4-a). The reaction temperature of the reaction is usually in the range of 0 to 120 ° C, and the reaction time of the reaction is usually in the range of 0.5 to 24 hours. After completion of the reaction, water is added to the reaction mixture, then the mixture is extracted with an organic solvent, and the organic layer is subjected to post-treatment operations such as drying and concentration, thus, the compound (4- b) can be isolated. The compound 23/100 isolate (4-b) can also be purified by chromatography, recrystallization and others. PRODUCTION METHOD 3 A compound (4-c) which is a compound represented by formula (1) in which n represents 0 and R 1 represents -SR 6x can be produced by reacting a compound (4-a) and a compound (6) in the presence of a base. [where, R 2 , R 3 , R 4 , R 6 , A 1 and A 2 represent the same meanings as described above], The reaction is usually carried out in the presence of a solvent. Examples of the solvent to be used in the reaction include ethers such as THF, dimethyl ethylene glycol and 1,4-dioxane, aromatic hydrocarbons such as toluene and xylene, nitriles such as acetonitrile, acid amides such as DMF, sulfoxides such as DMSO , and mixtures thereof. Examples of the base to be used in the reaction include alkali metal hydrides such as sodium hydride, and carbonates such as potassium carbonate. In the reaction, the compound (6) is usually used in a proportion of 0.5 to 10 moles with respect to 1 mole of the compound (4-a), and the base is usually used in a proportion of 0.5 to 10 moles with respect to 1 mol of the compound (4-a). The reaction temperature of the reaction is usually in the range of 0 to 100 ° C, and the reaction time of the reaction is usually in the range of 0.1 to 24 hours. After completion of the reaction, water is added to the reaction mixture, then the mixture is extracted with an organic solvent, and the organic layer is subjected to post-treatment operations such as drying and concentration, thus, the compound (4- c) can be isolated. The isolated compound (4-c) can also be purified by chromatography, recrystallization / 100% and others. PRODUCTION METHOD 4 A compound (4) which is a compound represented by formula (1) in which n represents 0 can be produced by reacting a hydrochloride of a compound (2) and a compound (3). [where, R 1 , R 2 , R 3 , R 4 , A 1 and A 2 represent the same meanings as described above], The reaction is usually carried out in the presence of a solvent, in the presence of a base. Examples of the base to be used in the reaction include tertiary amines such as diisopropylethylamine and triethylamine. Examples of the solvent to be used in the reaction include sulfoxides such as DMSO, aromatic hydrocarbons such as nitrobenzene, and mixtures thereof. In the reaction, compound (3) is usually used in a proportion of 0.5 to 3 mois with respect to 1 mole of compound (2), and the base is usually used in a proportion of 1 to 2 mois with respect to 1 mole of compound (2). The reaction temperature of the reaction is usually in the range of 50 to 200 ° C, and the reaction time of the reaction is usually in the range of 0.1 to 24 hours. After completion of the reaction, water is added to the reaction mixture, then the mixture is extracted with an organic solvent, and the organic layer is subjected to post-treatment operations such as drying and concentration, thus, the compound (4) can be isolated. The isolated compound (4) can also be purified by chromatography, recrystallization and others. PRODUCTION METHOD 5 25/100 A compound (4-d) which is a compound represented by formula (1) where n represents 0 and A 1 and A 2 represents = C (R 5 ) - can be produced by subjecting a compound (7) to an oxidation reaction in the presence of a base. [where, R 1 , R 2 , R 3 , R 4 and R 5 represent the same meanings as described above], The reaction is usually carried out in the presence of a solvent. Examples of the solvent to be used in the reaction include alcohols such as methanol and ethanol, water, and mixtures thereof. Examples of the oxidant to be used in the reaction include potassium ferricyanide. The base to be used in the reaction includes alkali metal hydroxides such as sodium hydroxide. In the reaction, the oxidant is usually used in a proportion of 1 to 5 mois with respect to 1 mol of the compound (7). The reaction temperature of the reaction is usually in the range of 0 to 100 ° C. The reaction time of the reaction is usually in the range of 0.1 to 24 hours. After completion of the reaction, the reaction mixture is extracted with an organic solvent, and post-treatment operations such as drying and concentration are carried out, in this way, the compound (4-d) can be isolated. The isolated compound (4-d) can also be purified by chromatography, recrystallization and the like. PRODUCTION METHOD 6 A compound (6) which is a compound represented by formula (1) in which n represents 1 can be produced by subjecting a compound (4e) to an oxidation reaction. 26/100 [where, R 11 represents a CrC6 chain hydrocarbon group optionally substituted by at least one member selected from Group X, a C3-C6 alicyclic hydrocarbon group optionally substituted by at least one member selected from Group X, phenyl group optionally substituted by at least one member selected from Group Y, 5-membered heterocyclic group optionally substituted by at least one member selected from Group Y, 6-membered heterocyclic group optionally substituted by at least one member selected from Group Y, OR®, -NR®R 7 , -NR®C (O) R 8 , -NR 6 CO2R 9 , -C (O) R 10 , -C (NOR®) R 10 , cyano group, nitro group or halogen atom, R 2 , R 3 , R 4 , A 1 and A 2 represent the same meanings as described above]. The reaction is usually carried out in the presence of a solvent. Examples of the solvent to be used in the reaction include aliphatic halogenated hydrocarbons such as dichloromethane and chloroform, acetic acid, water, and mixtures thereof. Examples of the oxidant to be used in the reaction include peroxyacids such as 3-chloroperbenzoic acid, hydrogen peroxide solution. In the reaction, the oxidant is usually used in a proportion of 1 to 3 moles with respect to 1 mole of the compound (4-e). The reaction temperature of the reaction is usually in the range of -20 to 100 ° C. The reaction time of the reaction is usually in the range of 0.1 to 24 hours, After completion of the reaction, water is added to the reaction mixture, then the reaction mixture is extracted with an organic solvent, and the organic layer is, if necessary, washed with an aqueous solution of a reducing agent and an aqueous solution of a base, and subjected to post-treatment operations such as drying and concentration, thus, the compound (8) can be isolated. The isolated compound (8) can also be 27/100 R 4 XI purified by chromatography, recrystallization and others. An intermediate in the present invention can be produced, for example, by the following method. INTERMEDIATE PRODUCTION METHOD 1 A compound (2) can be produced, for example, by the following method. —- XX - R 4 R (Ml) (M2) (2) [where, R 3 , R 4 , A 1 and A 2 represent the same meanings as described above]. STEP 1 A compound (M2) can be produced by reacting a compound (M1) and thiourea in the presence of a base. The reaction is usually carried out in the presence of a solvent. Examples of the solvent to be used in the reaction include alcohols such as methanol and ethanol, water, and mixtures thereof. Examples of the base to be used in the reaction include alkali metal hydroxides such as sodium hydroxide and potassium hydroxide. In the reaction, thiourea is usually used in a proportion of 0.5 to 3 millis with respect to 1 mol of the compound (M1), and the base is usually used in a proportion of 1 to 10 millis with respect to 1 mol of the compound (M1). The reaction temperature of the reaction is usually in the range of 0 to 100 ° C. The reaction time of the reaction is usually in the range of 0.1 to 24 hours. After completion of the reaction, an acid is added to the reaction mixture, then the mixture is extracted with an organic solvent, and the organic layer is subjected to post-treatment operations such as drying and concentration, thereby the compound (M2 ) can be isolated. The isolated compound (M2) can also be purified by chromatography, recrystallization and others. 28/100 STEP 2 Compound (2) can be produced by subjecting compound (M2) to a reducing reaction. The reducing reaction can be carried out in the presence of, for example, a metal powder such as an iron powder and zinc powder; an acid such as hydrochloric acid and acetic acid; and water. The reaction is usually carried out in the presence of a solvent. Examples of the solvent to be used in the reaction include ethers such as THF, ethylene glycol dimethyl ether and 1,4-dioxane, esters such as ethyl acetate and butyl acetate, alcohols such as methanol and ethanol, acid amides such as DMF , and mixtures thereof. The reducing agent described above includes an iron powder, zinc powder, stannous chloride and the like. In the reaction, a metal powder is usually used in a proportion of 3 to 10 moles with respect to 1 mole of the compound (M2). The reaction temperature of the reaction is usually in the range of 0 to 100 ° C. The reaction time of the reaction is usually in the range of 0.1 to 24 hours. After completion of the reaction, water is added to the reaction mixture, then the mixture is extracted with an organic solvent, and the organic layer is subjected to post-treatment operations such as drying and concentration, thereby the compound (2) can be isolated. The isolated compound (2) can also be purified by chromatography, recrystallization and others. In the following, specific examples of the present invention are shown below. In the table described below, Me represents a methyl group, Et represents an ethyl group, Pr represents a propyl group, iPr represents an isopropyl group, cPr represents a cyclopropyl group, tBu represents a tert-butyl group, cPen represents a cyclopentyl group, Ph represents a phenyl group, 2-Py represents a 2-pyridyl group, 3-Py represents a 3-pyridyl group, 4-Py represents a 4-pyridyl group, 1-Tz represents a 29/100 1,2,4-triazol-1-yl group, 1-Pz represents a pyrazol-1-yl group. Compounds represented by the formula (1) In the formula described above (1), the substituents R 1 , R 2 , R 3 , R 4 , A 1 , A 2 and n are combined as described in Table 1 to Table 38. Table 1 R 1 R 2 R 3 R 4 A 1 A 2 n F H cf 3 H = C (H) - ~ C (H) ~ 0 Cl H cf 3 H ~ C {H) “ 0 Br H cf 3 H = C (H) - = C (H) - 0 I H CF-j H "C (H) - * = C (H) - 0 Me H CF 3 H = C (H) - —C (H} - 0 Et H cf 3 H = C (H) - 0 Br H cf 3 H = C (H) - —C {H) - 0 cPr H cf 3 H -C (H) - = Ç {H) - 0 cf 3 n cf 3 H = C (H) - = C (H) - 0 CH3OCH2 H cf 3 H = C (H> - 0 Meo H cf 3 H = C {H) - = C (H) - 0 EtO H CF 3 K = C {H) - = C (HJ- 0 Pro H CF 3 H = C (H) - —C (H) - 0 CF 3 CH 2 O H cf 3 H = C (H) - = C (H5- 0 CHF2CH2O H cf 3 H = C (H) - -C (H) - 0 iPrO H cf 3 H = C (H> - = C (H) - 0 cPrCH 2 O H cf 3 H = C (H> - = C <H> - 0 cPenO H cf 3 K = C (H) - —C (H} - 0 Month H cf 3 H = C (H} - = C (H) - 0 MeS {0) H cf 3 K = C (H> - = C (H) - 0 MeS (O) z H cf 3 H = C (H} - -C (H) - 0 EtS H CF 3 H -C (H) - —C (H) - 0 EtS (O) H cf 3 H = C CH) - = C (H) - 0 EtS (Ü) 2 H cf 3 R = C (H) - = C (H) " 0 30/100 Table 2 R 1 R 2 R 3 R 4 A 1 A 2 n PrS H CF3 H = C (H) - = C (HJ- 0 PrS (0) H cf 3 H C (HJ- C (H) - 0 PrS (0) 2 H cf 3 H = C (H) - = C (H) ~ 0 iPrS H CF â H —C (H} - = C (H) - 0 iPrS (0) H cf 3 H = C (H) - C (H> - 0 ± PrS {0) 2 H cf 3 H CÍH) - C (H) - 0 CF3CH2S H CF H »C (H) - C (H) - 0 CHF 2 CK 2 S H cf 3 H C {H) - C (Ji} - 0 WtôHN H cf 3 H C (H) - C (H> - 0 Me 2 N H cf 3 H C <H) - C (H) - 0 Me (iFr) KI H cf 3 H C (H> - CÍH) - 0 CH 3 C (O) NH H cf 3 H C (H) - C (H) - 0 MeOC (O} NH H cf 3 H = C {H) - CÍH) - 0 HC {0) H cf 3 H = C (H) - C (H) - 0 CH 3 C (Q) H cf 3 H —C (H) - C (H) - 0 HC (NOMe) H cf 3 H C (H) - = C (H> - 0 CH 3 C (NOMe) H cf 3 H CÍH) - C (H) - 0 Ph H cf 3 H C (H) - —C (H) - 0 2-Py H cf 3 H CÍH) - C (H) - 0 3-Fy H cf 3 H C (H) ~ C (H) - 0 d-Fy H cf 3 H C (H) - = C (H) - 0 1-Tz H CFs H C (H) ~ C (H) - 0 1-Pz H cf 3 H C (H) ~ C (H) - 0 F H cf 3 H = -C ÍH) - CÍH) - 1 31/100 abela 3 R 1 R 2 R 3 R 4 A 1 The â n Cl H H = C {H) - = C (H) - 1 Br H cf 3 H = C (H) - = C {H) - 1 I H cf 3 H = C (H) - = C (H) - 1 Me H cf 3 H = C (H) - -C (M) - 1 Et H cf 3 H = C (H} - = C (H) - 1 Pr H cf 3 H = C (H) ~ = C (H} ^ 1 cPx K cf 3 H = C (H) - = C (H) - 1 CF 3 H cf 3 H »C (H) - -CÍH) - 1 ch 3 och 2 H cf 3 H = C (H) - 1 MeO H cf 3 H —C (H} “ = C (H) - 1 EtO H cf 3 H = C (H) - = C (H) - 1 Pro H cf 3 H = C (H) - = C (K} - 1 cf 3 ch 2 o H cf 3 H = C (H) - = C (H) - 1 chf 2 ch 2 o H cf 3 H —C (H) - -C (H) ~ 1 iPrO H cf 3 H = C (H) - = C (H) - 1 Ph H cf 3 H = C (end) ~ = C (H) - 1 F H cf 3 Cl —C (H) - —C (H) - 0 Cl H cf 3 Cl = C (H> - = C (H) - 0 Br H cf 3 Cl = C {H) ~ "C (H)" - 0 I H CF * Cl = C (HH = C (H) - 0 Me H CFs Cl = C (H} - = C (H) - 0 Et H CFs Cl = C (H) - = C (H) - 0 Pr H cf 3 Cl -C (H) - = C (H) ~ 0 cf 3 H CFs Cl = CÍH) - «C (H) - 0 32/100 out of 4 R * R 2 R 3 R 4 A 1 A 2 n CH3OCH2 H cf 3 Cl = C (H) - -C (H) - 0 MeO H cf 3 Cl = C (H> - = C (H) - 0 EtO H cf 3 Cl = C (fi) - = C (H) - 0 FrO H cf 3 Cl = C (H) - = C (H) - 0 GF3CH2O H cf 3 Cl —C (H) - = C (H) - 0 CHF2CH2O H cf 3 Cl · = C (H} - = C (H> - 0 iPrO H CF 3 Cl = C (H) - = C (H) - 0 Month H cf 3 ci = C (H) - -C (H) - 0 MeS (D) H CF3 Cl = C (H) - 0 MoS (0) 2 H cf 3 Cl = C (H} ’ = C (H) - 0 EtS H cf 3 Cl = C {H) - = C (H) - 0 Et3 (0) H CFa Cl = C (H) - = C (H) - 0 EtS (Ô} 2 H cf 3 Cl = C (H} - = C (H) " 0 PrS R cf 3 Cl = C (H) - —C (H) - 0 PrS (0) H cf 3 Cl —C (H) - = C (H) - 0 PrS (O) 2 H CF 3 C1C1 = C (HH = C <H> - 0 iPrS H cf 3 Cl = C (H) - = C (H) - 0 iPrS (0) H cf 3 Cl = C (H) - 0 iPrS (0} 2 H cf 3 Cl ~ C (H) * ~ 0 CF 3 CH 2 S H cf 3 Cl = C (H) - —C (H) - 0 chf 2 ch 2 s H cf 3 H = C (H) - —C (H) - 0 F H cf 3 H = C (H) - = C (C1) - 0 Cl H cf 3 H = C (H> - = C (C1) - 0 Br H cf 3 = C <C1} ~ 0 33/100 Table 5 R 1 R * R 3 R 4 A 1 A 2 n í H cf 3 H = C (H) - = C (Cl ·) - 0 Me H cf 3 H = C (H) - = C (Cl] - 0 Et H cf 3 H -C (H) ~ «= C (C1J- 0 Pr The cf 3 H = C (H) - = C (cl) - 0 CF 3 H CFs H —C (H) - = C (Cl) - 0 ch 3 och 2 H cf 3 H = C (H) - = C (C1) - 0 MeO H cf 3 H = C (H) - = CICLE1) - 0 EtO H cf 3 H = C {H) ~ = C (C1) - 0 Pro The cf 3 H "C (H) - = c (cn- 0 CF 3 CH 2 O H cf 3 H = C (C1) - 0 CHF2CH2O H CFs H = C (H) - = C <C1) ~ 0 iPrO H cf 3 H = C (H) - = C (C1) ~ 0 Month H cf 3 H = C (C1) ~ 0 MeS (0) H cf 3 H = G (H) - = C (C1) - 0 Month (Ok H cf 3 H = C (H) - = C (C1) - 0 EtS H cf 3 The —C (H) - = C (C1) - 0 EtS (O) H cf 3 H C (H) “ = C (C1) ~ 0 EtS (0) 2 H CFa H = C (H) - = C {C1) “ 0 PrS H GFg H = C (C1) - 0 PrS (Q) H cf 3 H = C (H) - C (C1) - 0 PrSCOk H cf 3 H = C (H) ~ -C (Cl) - 0 iPrS H cf 3 H = C (H> - -C (C1) ~ 0 iPrS (0) H cf 3 H = C (H) - -C (C1) - 0 iPrS (0) 2 H cf 3 H -c (ci) - 0 34/100 Table 6 R 1 R 2 R 3 R 4 A 1 A 2 n cf 3 ch 2 s H cf 3 H -C (ci) - ' 0 chf 2 ch 2 s H cf 3 H = c (ci) - 0 Cl Cl cf 3 H = C (H) - 0 MeO Cl cf 3 H -C (H) - -C (HJ- 0 EtO Cl cf 3 H = C (H) ~ = C (H) - 0 Pro Cl cf 3 H = C (H) ~ -C (HJ- 0 cf 3 ch 2 o Cl cf 3 H = C (H) ~ = C (HJ- 0 chf 3 ch 2 o Cl cf 3 H = C (H) - = C (HJ- □ ± PrO Cl cf 3 H = C (HJ - = C (H) - 0 Month Cl cf 3 H —C (H) - = c (H) - 0 MONTH (O) Cl cf 3 H = C (H) - -C (H) - 0 MeS (0) 2 Cl cf 3 H = C (H) - = C (H) - 0 EtS Cl cf 3 H = C (H) - = C (H) ~ 0 EtS (O) Cl cf 3 H = C (H) - = C (H) - 0 EtS (OJ2 Cl cf 3 fi = C {H} ~ = C (H) - 0 CF 3 CH 2 S Cl cf 3 H = C <H) - = C (H) " 0 chf 2 ch 2 s Cl cf 3 H = C (H) - 0 MeHN Cl cf 3 H = C (H) - = C (H> - 0 Me 2 N Cl cf 3 H -C (H) - = C (H) - 0 Month (iPr) N Cl cf 3 H = C (HJ- = C (H) - 0 Cl F cf 3 H = C (HJ- = C (H] - 0 MeO F cf 3 H = C (K) - = C (H) - 0 EtO F cf 3 H == C (HJ- 0 Pro F cf 3 H "C (HH = C (H) ~ 0 35/100 Table 7 R 1 R 2 R 3 R 4 THE* A 2 n CF3CH2O F cf 3 H —C (H) - -C (H) - 0 CHF 2 CH 2 O F cf 3 H —C {H) “ = C (HH 0 ipro F cf 3 H = C (H) - ~ C (H) ~ 0 Month F cf 3 H = C (H) - = C (H) - 0 MeS (0) F CFs H = C (H} - = C (H) - 0 MeS (O> 2 F cf 3 H = C (H) - C (H) - 0 EtS F cf 3 H = C (H5- = C (H> - 0 Effectiveness) F CF a . H = C (H) - 0 EtS (O) z F CF 3 H = C (H) - = C (H) ~ 0 CF3CH2S F cf 3 H = C (R) - 0 chf 2 ch 2 s F CF 3 H «C (H) - = C (H) - 0 MeHN F cf 3 H = C {K) - = C (HJ- 0 Me 2 N F cf 3 H = c (H) - = C (H) - 0 Me (íFr) M F cf 3 H = C (H | - = C (H) - 0 F H CP 3 O H = C (H) - = C (H) - 0 Cl H cf 3 q H = C (H) - 0 Br H cf 3 o H = C (H) - 0 I H CF3O H = C (H) - = C (H) - 0 Me H CF3O H = C (H) - = C (H} - 0 Et H CF3O H —C (H) - = C (H) - 0 Pr H cf 3 o H = C (H) - = C (H) - 0 cPr H cf 3 o H —C (H) - = C (H) - 0 cf 3 H cf 3 o H = C (K) - —C (H) - 0 CH3OCH2 H cf 3 o H = C (H> - = C (H) - 0 36/100 Table 8 R 1 R 5 R 3 R 4 to 1 A 2 n MeO H CF3O H = C (H) - -C (H) - 0 EtO K CF 3 O H = C {H} - 0 Pro H CF3O H = C (H) - —C (H) - 0 cf 3 ch 2 o H cf 3 o H = C (H) - = C (H) - 0 CHFaCH z O H cf 3 o H —C (H) - —C (H} ~ 0 iPrO H cf 3 o H "C {H) ~ = C (H> - 0 cPrCHgO H cf 3 o H = C (H) - C (H) - 0 COOPY H cf 3 o H -C (H) - = C (H) - 0 Month H CFaO H = CÍH) - —C (H) - 0 MeS (O) H CF 3 O H —C (H} - 0 MeS (0) z H CF 3 O H = C (H) - —C (H) - 0 EtS H cf 3 o H = C (H) - = C (H) ’ 0 EtS (0) H cf 3 o H = C (H) ~ = C (H) - 0 EtS (O) 2 H CF3O H = C (H) - = C (H) - 0 PrS H CF3O H = C (H} - = »C (H)“ 0 PrS (0) H cf 3 o H = C (H) ~ 0 PrS (0) 2 fi cf 3 o H = C (Ji) - = C (H) - 0 iPrS H GF3O H = C (H) ~ = C (H} - 0 iPrS (0) H cf 3 o H = C (H) - = C (H) - 0 iPrS (O) 2 H CF3O H = C (H) - = C (H) - 0 CF 3 CH 2 S H cf 3 o H = C (H) ~ -C (H) ~ 0 CHF2CH2S H cf 3 o H = C (H) ~ = C (H) - 0 MeHN H cf 3 o H = C (H) " 0 Me 2 W H cf 3 o H = C (H> - = Ç (H) - 0 37/100 abela 9 R1 R 2 R 3 R 4 A 1 A 2 n Me (iPr) N H cf 3 o H = C (H) - = C (H) - 0 CH 3 C (O) NH H cf 3 o H = C (H) - = C (H) - 0 MeOC (O) NH H cf 3 o H = C (H) - = C {H) - 0 HC (0) H cf 3 o H = C (H) ~ = C (H) - 0 CH 3 C (O) H cf 3 q H = C (H) - = C (H) - 0 HC (NOMe) H cf 3 o H = C (H) - = C (H) - 0 CH 3 C (NOMe) H cf 3 o H C (H) “ = C £ H) - 0 Ph H CF S O H = C (H) - = C (H) ~ 0 2-Py H CFjO H = C (H) - = C (H) - 0 3-py H cf 3 o H = C (H) - = C (H) - 0 4-Py H cf 3 o H = C (HJ- = C (H) - 0 1-Tz H CF3O H = C (H> - «C <H) ~ 0 1-Fz H cf 3 o H = C (H) - = C (H) - 0 F H cf 3 o H = C (H} ~ = C (H) - 1 CI H cf 3 o H = C (H) - = C (H) - 1 Bx H cf 3 q H = C (H) - 1 I H cf 3 o H = C (H) - = C (H} - 1 Me H CFgO H -C (H) - = C (H) - 1 Et H CF3O H = C (H) - = C (H) - 1 Px H CF3O H = C (H) - = C (H) - 1 CPX H CF3O H = C (H) - = C <H> - 1 cf 3 H CF3O H = C (H) - —C {H) - 1 CKsOCHz H CF3O The = C (H) - = C (H) - 1 MeO H cf 3 o H = C (H) - = C (H) - 1 38/100 abela 10 R 1 R 2 R 3 EtO faith CFgO Pro H CFgO CF3CH2O H CF3O CHFsCHaO H CF 3 O OWN H cf 3 q Ph H cf 3 o F H cf 3 s CL H CFgS Br H CF 3 S I H cf 3 s Me faith cf 3 s Et H cf 3 s Pr H cf 3 s cPr H cf 3 s CFg H cf 3 s CH3OCH2 H cf 3 s MeO H CFaS EtO H cf 3 s Pro H cf 3 s CF 3 CH 2 O H cf 3 s CKF 2 CH at 0 H cf 3 s iPrO H cf 3 s cPrCHzO H CFgS cPenO H cf 3 s R 4 A 1 A 2 n H = C (H> - 1 H = C (H) ~ = C (H) ~ 1 H = C (H) - = C (B) - 1 H = C (H - 1 H »C (H) - = C (H) - 1 H = C (H) - -C (H) ~ 1 H = C (H) - = C (H) - 0 H = C (H) - = C (H) - 0 H = C (H> - = C (H) ~ 0 H = C {H) - 0 H = C (H) ~ —C {H) - 0 H = C (H) - = C (H) - 0 faith = C (H) - 0 H = C (H) " "C (H) - 0 H = C (H) - "C (H) - 0 H C (H} - = C (H) - 0 H = C (H) - = C (H) - 0 H = C (H) - = C (H) - 0 H —C (H) - = C (H) - 0 H = C (H) - 0 H = C (H) - = C (H) - 0 H = C (H) - = C (Hj- 0 H = C (H) ~ = C (H) - 0 H = C (n) - -C (H) - 0 39/100 Table 11 R 1 R 2 R 3 R 4 A 1 A 2 n Month H cf 3 s H = C (H) - -C (H) - 0 MôS (0) H cf 3 s H = C (H) - = C (H) - 0 MeS (O) 3 H cf 3 s AND = C (H) - = C (H) - 0 EtS B CFaS H = C (H) - = C (H} - 0 EtS (O) H cf 3 s H = C (H) " "C (H)" 0 EtS (O) 2 H CFjS H »CÍH) - = C (H) - 0 PrS H CF 3 S H = C (H) - = C (H) - 0 PrS (O) H CFgS H = C (H) - = C (H) - 0 PrS (O) 2 H CFaS H = C (H) - 0 iPxS H CF s S H -C (H) - = C (H) - 0 iPicS (0) H CF 3 S H —C (H) - = C (H) - 0 iPrS (0) 2 H cf 3 s H -C (H) - = C (H) - 0 cf 3 ch 2 s H cf 3 s H = C (H) - = C (H) - 0 CHF 2 CH2S H CFsS AND = C (H) - = C (H) " 0 MeHN H cr 3 s H «C (H) - 0 Me 5 N H cf 3 s H -CÍH) - —C (H) - 0 Me (iPr) N H cf $ 3 H —C (H) - = »C (H) - 0 CH 3 C (O) NH H cf 3 s H = C (H) - = C (H) - 0 MeOC (O) NH H CFgS faith = C (H) - = C (H) - 0 HC (O) H CFsS H = C (H) - = C (H) ~ 0 CHaC (O) H CF 3 S H = C (H) - = G (B) - 0 HC (NOMe) H cf 3 s H = C (H) - 0 CHsC (NOMe) H cf 3 s H = C (H) - -C (H) - 0 Ph H cf 3 s H = C (H} - = C (HJ- 0 40/100 Abela 12 R 1 R 2 R 3 R 4 A x A 2 n 2-Py H cf 3 s H = C (H) - 0 3-Py H CFgS H = C (H) - = C (H) - 0 4-Py H CFjS H = C (K) - = C (H) - 0 1-Tz H CFgS H = C (H) - = C (H) - 0 1-Pz H cf 3 s H = C (H) - 0 F H cf 3 cf 2 H = C (H) ~ = C (H) - 0 Cl H CFgCFj! H = C {H) - = C (H) - 0 Br H cf 3 cf 2 H = C (H) - = C {H) - 0 I H cf 3 cf 2 H = C (H) - = C (H> - 0 Me H cf 3 cf 2 H = C (H) - = C (H) - 0 Et H cf 3 cf 2 H "C (H) - = C (H> - 0 Pr H cf 3 cf 2 H = C (H) - —C (H) - 0 cPr H cf 3 cf 2 H = C {H) - = C (H) - 0 cf 3 H CF3CF2 H = C (H) - = C (H) - 0 ch 3 och 2 H cf 3 cf 2 H 0 MeO H cf 3 cf 2 H —C (H) - 0 EtO H cf 3 cf 2 H -C (H) - = C (E) - 0 Pro H cf 3 cf 2 H -C (H> - —C (H) - 0 CF 3 CH 2 o H CF3CF2 H = C <H) - = C <H) ~ 0 CHF2CH2O H cf 3 cf 2 H = C (H) - = C (H) - 0 iPrO H cf 3 cf 2 H = C (H) - = C (H) - 0 cPrCH 2 O H cf 3 cf 2 H ~ C (H) ~ = C (H) - 0 cPenO H cf 3 cf 2 H —C (H) - = C (H) - 0 Month H cf 3 cf 2 H —C (H) - = C (H) - 0 41/100 Table 13 R 1 R 2 R 3 R 4 A 1 A 2 n MeS (0) H CF 3 CF 2 H = C (H) - -C (K) ~ 0 MeS (0) 2 H CF 3 CF 2 H = C (H) - = C (H) - 0 EtS H CF 3 CF a R = C (H) - = C (H) - 0 EtS (0) H CF3CF2 H -C (H} - = C (H) - 0 EtS (0) 2 H CF3CF2 H = C (H) - 0 PrS H CF3CF2 H = C (H) - —C {H) - 0 PrS (O) H CF3CF2 H = C (H) - = C (H) - 0 PrS (O) 2 H cf 3 cf 2 H —C (H) - = C (H) - 0 iPrS H cf 3 cf 2 H -C (H) - 0 iPrS (0) H cf 3 cf 2 H = C (H) - = C (H) - 0 IPrS (O) 2 H CF3CF2 H = C (H) - = C (H) - 0 CF 3 CH 2 S H cf 3 cf 2 H = C (H) - = C (H) - 0 CHFíCHí-S H CF3CF2 H = C (H) - = C (H) - 0 MeHN H cf 3 cf 2 AND = C (H) - = C (H) - 0 Me 2 N H cf 3 cf 2 H = C (HJ- = C (H) - 0 Me (iPr) N H cf 3 cf 2 K = C (H) - = C (H) - 0 Pfc H cf 3 cf 2 H = C (H) - = C (H) ~ 0 2-Py H cf 3 cf 2 H = C (H} - = C (H> - 0 3-Py H cf 3 cf 2 H = C (H) - = C (H) - 0 4-Py H cf 3 cf 2 H —C (H) - -C (H) - 0 1-Tz H gf 3 cf 2 H = C (H) - 0 1-Pz H cf 3 cf 2 H = C (B) - = C (H> - 0 F H (CF 3 ) 2 CF H = C (H) - = C (H> - 0 Cl H (CF 3 ) 2 CF H = C (H) - = C (H) - 0 42/100 Table 14 R 1 R 2 R 3 R 4 A 1 A 2 n Br H (CF 3 ) 2 cf H = C (H) - = C <H) - 0 I H (CF 3 ) 2 CF H = C (H} ~ = C (H) " 0 Me H (CFDsCF H = C (H) " = C (H> - 0 Et H (CF 3 ) íCF H = C (H) - = C (H) ’ 0 Pr faith (CF 3 ) 2 CF H = C {H) - = C (H) - 0 cPr H (CF 3 ) 2 CF H = C (H) - = C (H} - 0 cf 3 H (CF 3 ) 2 CF H = C (H) - = C (H) - 0 CH3OCH2 H (CFskCF H = C (H) - —C (H) - 0 MeO H (Cr 3 ) 2 CF H = C (H) - 0 EtO faith <CF 3 ) 2 CF H —C (H) - —C {H) - 0 Pro faith (cf 3 ) 2 cf H = C (H) ~ = C (H) - 0 CF3CH2O H (CF 3 ) 2 CF H = C (H) - = C (H) - Ü CHF2CH2O H (CF 3 ) 2 CF H = C (H) - D iPrO H (cf 3 ) 2 cf H = C (H) - = C (H) - 0 cPrCH 2 O H (cf 3 ) and çf H = C (H) - = C (H) - 0 cPenO H (cf 3 ) 2 cf H ~ C (H) - C (H) - 0 Month H (CF 3 ) z CF H -C (H) ~ = C (H) - 0 MeS (O) H (CF 3 ) z CF faith = C (H) - = C (H) ~ 0 MeS (O) 2 H (CF 3 ) 2 CF H = C (H) - = C (H) - 0 EtS H (CF 3 ) 2 CF H = C (H) - = C (H) - 0 EtS (0) H (CF 3 ) 2 CF H = C (H) - 0 EtS (0) 2 H <CF 3 ) 2 CF H -C (H) - 0 PrS H <cf 3 ) 2 cf H = C (H) - = C (H> - 0 PrS (0) H (CF3I2CF H —C (H) - = C (Ji) - 0 43/100 Table 15 R 1 R 2 R 3 R â A 1 A 2 n PrS (0) 2 H (CF 3 ) 2 CF H = C (H) - = C (H> - 0 iPrS H (CF 3 ) 2 CF H = C (H) - = C (H) ~ 0 · IPrS (O) H (CF 3 ) 2 CF H = C (H) - —C (H) “ 0 iPrS {0) 2 H (cf 3 ) 2 cf H «C (H) - = C (H) - 0 çf 3 ch 2 s H {CF 3 ) 2 CF H = C {H) - = C (H) - 0 CHF 2 CH 2 S H {CF 3 ) 2 CF H = C (H) - = C (H) - 0 MeHN H ícf 3 ) 2 cf H -C (H) - = C (H) - 0 Me 2 N H ÍCFaJzCF H = C (H) - = C (H) - 0 Me (iPr) N H {CF 3 ) 2 CF H ”C (H) - = C (H) - 0 Ph H {CF 3 ) 2 CF H = C (H) - = C (H) - 0 2-Py H (CF 3 ) 2 CF R = C (K) - = C {H> - 0 3-Py H (cf 3 } 2 cf H = C (H) - 0 4-Py H (cf 3 ) 2 cf H = C (H) - = C (H) - 0 1-Tz H CCF 3 ) 2 CF H = C (H) - = C (H) - 0 1-Pz H (CF 3 ) 2 CF H = C <H) - = C (H) - 0 F H CFj H = C (H) - N 0 Cl H CFs H = C (R) - N 0 Br H cf 3 H = C (H) - N 0 I H cf 3 H -C (H} - N 0 Me H cf 3 H ~ C (H) - N 0 Et H CF 3 H = C (H) - N 0 Fr H CF S H = C (H) - N 0 cPr H CF 3 H —C (H) - N 0 cf 5 H cf 3 H = C (H) - N 0 44/100 Table 16 R 1 r 2 R 3 R 4 A 1 A 11 CH3OCH2 H CFg H = C (H) - N 0 MeO H cf 3 H = C (H) - N 0 EtÔ H cf 3 H = C (H) - N 0 Pro H cf 3 H = C (H) - N 0 CP 3 CH £ O H cf 3 H C (H) - N 0 CHFsCHsO H cf 3 H = C (H> - N 0 iPrO H cf 5 H = C (H> - W 0 cPrCH ^ O H CF3 H = C ÍH) - R 0 cPenO H çf 3 H = C (H> - N 0 Month H cf 3 H = C (H> - N 0 MeS (0) H cf 3 H —C (H> - N 0 MeS <0) 2 H CF 3 H = C (H) - N 0 EtS H cf 3 H = C {H) - N 0 EtS (0) H CFg H = C {H) - N 0 EtS (0) 2 H CF 3 H R 0 PrS H CFg H = C {H) ~ N 0 Prs (o) H CFs H = C {H) - N 0 i PrS (0} 2 ' H CF3 H = C (H) - R 0 iPrS H CFs H = C <H) - R 0 iPrS (O) H CFg H = C {H) - R 0 iPrS (O) 2 H CF 3 H «C (H) - R 0 cf 3 ch 2 s H cf 3 H = C (H) - N 0 chf 2 ch 2 s H cf 3 H = C <H) - N 0 MeHN H cf 3 H N 0 45/100 Table 17 R 1 R 2 R 9 R 4 A 1 A 5 n Me 2 N H cf 3 H —CÍH) - N 0 Me (iPx) N H cf 3 H -C (H) - N 0 CH 3 CÍO) NH H cf 3 H = C <H) - N 0 MeOC (O) NH H cf 3 H —C {H) - N 0 HC (0) H cf 3 H = C (H) - N 0 CH 3 C (0) H cf 3 H = C (H) - N 0 HC (NOMe) H cf 3 H = C (H) - N 0 CH 3 C (NOMe) H cf 3 H = C (H) - N 0 Ph H cf 3 H "C (H) - N 0 2-Py H cf 3 H = C (H) - N 0 3-Py H cf 3 H —C (H) - N 0 4-Py H cf 3 H (H) - N 0 1-T2 H cf 3 H = C (H) - N 0 1-Pz H cf 3 H -C (H) - N 0 F H cf 3 H C (H) - N 1 Cl H cf 3 H = C (H) - N 1 Br H cf 3 H = C (H) ~ N 1 I H cf 3 H = C (H) - H 1 Me H H —C (H) - K 1 Et H cf 3 H = C (H) - N 1 Pr H CFs H = C (H) - N 1 cPr H CFJ H = C (H) - N 1 Cf 3 H CFs H = C (H) - N 1 ch 3 och 2 H CFs H = C (H) - N 1 46/100 Table 18 ! r1 R 2 R 3 R ^ A 1 A 2 n I MeO H CF S H = C (H) - N 1 ! EtO H cf 3 H = C (H) - N 1 Pro H cf 2 H = C (H) - N 1 CF 3 CH 2 O H cf 3 H = C (H) - N 1 CHE2CH2O H cf 3 H = C (H) - N 1 iPrO H cf 3 H = C (K) - N 1 Ph H cf 3 H = C (H) - N 1 F H cf 3 H N 0 Cl H cf 3 H N 0 Br H cf 3 H N = C (H) - 0 I H cf 3 H N = C (H) - 0 Me H CF 3 H N = C (HH 0 Et H cf 3 H N = C (H) - 0 Pr H cf 3 H N 0 cPr H cf 3 H N = C (H) - 0 cf 3 H cf 3 H N = C (H) - 0 ÇH3OCH2 H cf 3 H N = C (H) - 0 Meo H cf 3 H u = C {H) - 0 EtO H cf 3 H W = C (H) ~ 0 Pro H cf 3 H N 0 CF3CH2O H cf 3 H N = C (H> - 0 chf z çh 2 q H cf 3 H N -C (H) ~ 0 iPrO H cf 3 H N = C (H> - 0 cPrCH 2 0 H CFs H N = C (H> 0 47/100 Table 19 R 1 R 2 R 3 r 4 A 1 A 5 n cPenO H cf 3 H N = C (n) - 0 Month H cf 3 H N -CÍH) - 0 MeS (0) H cf 3 H K = C (H) - 0 MeS (Q} 2 H cf 3 H K = C (H) - 0 EtS H CF 3 H K = C (HI- 0 EtS (O) H cf 3 H w = C (H) - 0 EtS [0) 2 H cf 3 H ϊί —C (H) - 0 PrS H CFs H N = C (H) - 0 PrS (O) H CFs H N = C [H) - 0 PrS (O) 2 H CFs H N = CÇH) - 0 iPrS H cf 3 H N -CÍH> ~ 0 iPrS (0) H cf 3 H N = CÍH) - 0 iPrS (O) 2 fi CFs H N = C (H) - 0 CF 3 CH Z S H CF 3 H K = C (H) - 0 CHFgCHjS H cf 3 H N = C {H) - 0 MeHN H cf 3 H N = C {H) - 0 H cf 3 H N = C (H) " 0 Me (iPr) N H cf 3 H W = C (H) - 0 CH 3 C (O) NH H cf 3 H N = C (BH 0 MeOC (O) NH H cf 3 H W = C (H) - 0 HC (O) H cf 3 H N = C {H) - 0 CH â CíO> H CFs H N 0 HCYNOMe) H CFs H N = C [H) - 0 CH 3 C (NOMe) H CF 3 H N = C (H) - 0 48/100 Table 20 R 1 R z R 3 R 4 A 1 A 2 n Ph H cf 3 H N = C (R) - 0 2-Py H cf 2 H N = C (H) - 0 3-Py H cf 2 H N = C (H) - 0 4-Py H cf 3 H N 0 1-Tz H CFs H N = C {H) - 0 1-Pz H cf 3 H N = C (H) - 0 P H -cf 2 ocf 2 - = C (H) - = C (H) - 0 Cl H -CF2OCF2- = C (H) - 0 Br H -CF 2 QCFj- 0 I H -CF 2 0CF 2 - —C (H) - 0 Me H -CF2OCF2- = C (H) - —C (H) - 0 Et H -cf 2 ocf 2 - = C (H) - = C (H) - 0 Pr H ”CF 2 OCF 2 ~ C (H) - «C (H) - 0 cPr H 'CF 2 OCF 2 - = C (H) - = C (H) ” 0 cf 3 H -cf 2 ocf 2 - = C (H) ’ = c (H3 - 0 ch 3 och 2 H -CFzOCFz- = C (H) - = C (H5- 0 MeO K -CF 2 0CF 2 - = C (H) - = C (H) - D EtO H ~ CF 2 QÇF 2 ~ = C (H) - 0 Pro H -CF2OCF2- = C (H) - 0 CF 3 CH 2 O H -CF Z OCF Z - = C {H) - = C (H) - 0 chf 2 ch 2 o H -CF 2 OCF 2 - = C (H) - = C (H) - 0 IPrO H -cf 2 ocf 2 - = C (H) - = C (H) - 0 ' cPrCH 2 O H -cf 2 ocf 2 - = C (H) - = C (H) - 0 cPenO H -CF2OCF2- = C (H) - = C (H) - 0! 49/100 Table 21 R 1 R 2 R 3 R 4 A 1 A z n Month H -cf 2 ocf 2 - = C (H) - = C (H) - 0 But (0} H -cf 2 ocf 2 - = C (H> - = C (H) - 0 MeS (0) 2 H -cf 2 ocf 2 - = C (H> - = C (H) - 0 EtS H -CF2OCF2- C (H} - = C (H) ~ 0 EtS (0) H -cf 2 ocf 2 - -C (H) - = C (H) - 0 EtS (O) â H -CF2OCF2- = C (H) - —C (H) - 0 PxS H -CF2OCF5- -CÍH) - -C (H) ~ 0 PrS (O) H -CF2OCF2- = C (H) - = C (H) - 0 PrS (0) 2 H -CF2OCF2- = C (H) - = C (H) - 0 iPrS H -CF2OCF2- = C (H) - = C (H) - 0 ÍPrS (O) H -CF2OCF2- -CÍH) - = C (H) - 0 iPrS (O) 2 H -cf 2 ocf 2 - = C (H> - . = C (H) - 0 cf 3 ch 2 s H -cf 2 ocf 2 - = C (H) - «= C (H) - 0 chf 2 ch 2 s H -CF2OCF2 ’ -CÍH) - = C (H) - , 0 MeHN H -CF2OCF2- = C (H) - —CÍH} - 0 Me 2 N H -CF2OCF2- = C (H) - = C (H) - 0 Me (iPr) W H ~ cf 2 oc F 2 - -CÍH} - = C (H) - 0 CH 3 C (O) NH H -CF2OCF2- = C (H) ~ -C (H) - 0 MeOC (O) NH H -CF 2 OCF 2 “ -C (H) - = C <H) - 0 HC (O) H -CF 2 0CF 2 - = C (H) - = C (B) - 0 CH 3 C (O) H -cf 2 ocf 2 - = C {H} - = C (H) - 0 HC (NOMe) H -cf 2 ocf 2 - -C (H) - = C (H) - 0 CH 3 C (NOMe) H -CF 2 OCF £ - -C (H) - —C (H) - 0 Ph H -CF 2 0CF 2 - = C (H) - —C (H) - 0 50/100 Table 22 R 1 R 2 R 3 R 4 A 1 A z n 2-Py H -cf 2 ocf 2 - = C (H) - z = C (H) » 0 3-Py H -CFaOCFa- »C (H) - = C (H) ~ 0 4-Py H -CFaOCFz- = C (H) - = C (H) - 0 1-Tz H -CF2OCF2- = C (H) - = C (H) ~ 0 1-Pz H -CF2OCF2- = C (H) - 0 F. H -cf 2 ch 2 ch 2 - 0 Cl H -cf 2 ch 2 ch 2 - = C (HH 0 Br H -cf 2 ch 2 ch 2 - = C (H) - = C (H} - 0 I H -CF to CH 2 CH 2 - = C (H) - = C (HJ- 0 Me H -CF 2 CH 2 CH 2 0 Et H -cf 2 ch z ch 2 - = C (H) - = C (H) - 0 Pr H -cf 2 cb 2 ch 2 - = C (hH -C (H) - 0 cPr H -CF s CH 2 CH 2 - = C (fl) - = C (H) - 0 cf 3 H -cf 2 ch 2 ch 2 - = C (H} - = C (H) - 0 CK 3 OCK 2 H -cf 2 ch 2 ch 2 - = C (H) - 0 MeO H -CF2CH2CH2- —C (H} “ 0 EtO K -cf 2 ch 2 ch 2 - = C <H) - = C (H) - 0 Pro H -CF2CH2CH2- = C <H) ~ = C {H) - 0 CF3CH2O H -cf 2 ch 2 ch 2 - = C (H) ’ —C (H) - 0 ÇHF2CH2O H -cf 2 ch 2 ch 2 - = C (H) - = C (H) - 0 iPrO H -cf 2 ch 2 ch 2 - = C (H) - = C (H) - 0 cPrCH 2 0 H -cf 2 ch 2 ch 2 - 0 cPenO H -cf 2 ch 2 ch 2 - = C (H) - = C {H) - 0 Month H -cf 2 Ch 2 ch 2 - = C (H) - = C (H) - 0 51/100 Table 23 R 1 R 2 R 3 R 4 A 1 A 2 n MeS (0) H -CF2CH2CH2- —C (H} - -C (H) - 0 MeS (0) 2 H -CF £ CH 2 CH 2 - = C (H) - = C (H) - 0 EtS H ~ cf 2 ch 2 ch 2 - = C (H) - = C (H) - 0 EtS (0) H -CF2CH2CH2- = C (H) - 0 EtS (0) 2 H -CF 2 CH 2 CH 2 - —C (H) - -C (H) - 0 PrS H -CF2CH2CH2- = C (H) - = C (K) - 0 PrS (0) H -CF 2 CH2CH 2 - = C (H) - = C (H) - 0 PrS (0) 2 faith -cf 2 ch 2 ch 2 - -C (H) - = C (H) - 0 iPrS H -CF2CH2CH2 ’ «C (H) ~ = C (H) - 0 iPrS (O) H -cf 2 ch 2 ch 2 - = C (H) - = C (H> ~ 0 iPrS <0) 2 H -cf 2 ch 2 ch 2 - = C (H) - = C (H} - 0 cf 3 ch 2 s H -CF2CH2CH2- = C (H) ~ = C (H) - 0 · chf 2 ch 2 s H -CF 2 CH 2 CH 2 - = C (H> - —C (H) - 0 MqPN H -cf 2 ch 2 ch 2 - = C (H> - = C (H) ’- 0 Me 2 N H -CF2CH2CH2- = C (H) ~ = C (H> - 0 Me (iPr) N H -cf 2 ch 2 ch 2 - = C (H) - = C (H) - 0 F H -ch 2 ch 2 cf 2 - = c (li) - = C (H> - 0 Cl H -CH2CH2CF2- = C (H) - = C (H) - 0 Br H -CH 2 CH 2 CF 2 “ = C (H) - = C (R) - 0 I H -CR 2 CH 2 CF 2 - = C (H) - 0 Me H -CH 2 CH z CF 2 - = C (H) - = C (H) - 0 Et H -CH 2 CH 2 CF 2 - = C (K) - «C (H) - 0 Pr H -CH2CH2CF2- = C (H) ~ = C {H) “ 0 cPr H -CH 2 CH 2 CF 2 - —C (H) ~ = C {H} - 0 52/100 Table24 R 1 R 2 R 3 R 4 A 1 A z n cf 3 H "CH2CH2CF2- = C (H) - = C (H) - 0 CH3OCH2 H ~ CH 2 CK 2 CF 2 - = C (H> - = C (H) - 0 MeO H -ch 2 ch 2 cf 2 - -C (H) - = C (H) - 0 EtO H -ch 2 ch 2 cf 2 - = C (H) - = C (H) - 0 Pro H -CH2CH2CF2- = C (H) - = C (K) " 0 CF5CH 2 O H -ch s ch 2 cf 2 - = C (H) - = C {H) - 0 CHF2CH2O H -CH2OH2CF2- = C (H) - —C (H) - 0 iPrO H -Ch 2 ch cf 2 - = C (H) - 0 cPrCH 2 O H -CH2CH2CF2- = CÍH> - = C (H) - 0 cPenO H -CHaCHsCFa- = C (H) - = C (H) - 0 Month H -ch 2 ch 2 cf 2 ~ = C (H) ~ 0 MeS (0) H -ch 2 ch 2 cf 2 - = C (H) ~ = C <H) - 0 MeS {0) 2 H -ch 2 ch 2 cf 2 - = C (H) - = C (H> - 0 EtS H -CH 2 CH Z CF2- = C (H) - = C (H) - 0 EtS (0) H -CH 2 CH 2 CF 2 - = C (H) - —C (H) - 0 EtS (O) 2 H -ch 2 ch 2 cf 2 - = C (H) - —C (H) - 0 PrS H -CH2CH 2 CF 2 “ = C (H) ~ 0 PrS (0) H -CH2CH 2 CF 2 ~ »C (K) - = C (H) - 0 PrS (0) 2 H -ch 2 ch 2 cf 2 - = C (H) - = C (S) - 0 iPrS H -ck 2 ch 2 cf 2 - = C (H) - = C (H) - 0 iPrS (0) H -CH2CH2CF2- = C (H) - = C (H) - 0 iPrS (0) 2 H -CH2CH2CF2- —C (H} - = C (H) - 0 CF3CH2S H -CH2CH2CF2- = C (H) - = C (H) - 0 CHF2CH2S H "CH2CH2CF2- = C (H) - = C (H) - 0 53/100 Table R 1 R z R 3 R * A 1 A 2 n MeHH H -CH 2 CK 2 CF 2 - C {H) - = C (H) - “ 0 Me 2 N H -CH 5 CH to CF 2 - C <H) - CÍH) - 0 Me (iPr) N H -ch 2 ch 2 cf - = C (H) - C (H) - 0 F H -cf 2 ch 2 ch 2 ch 2 - CÍH) - C (H) - 0 Cl H -cf 2 ch 2 ch 2 ch 2 - = C (H) - C (H) - 0 Br H -CF2CH 2 CH 3 CH 2 - -C (H) - C <H) - 0 I H -CF 2 CH 2 CH 2 CH 2 - C (H) ~ C (H) - 0 Me H -cf 2 ch 2 ch 2 ch 2 - = C (H> - C (K) - 0 Et H -CF 2 CH z CH 2 CH 2 - C (H} - CÍH} - 0 Pr H -CF Z CH 2 CH 2 CH 2 - C (H) - C (H) - 0 cPr H -CFsCHsCHzCHs- C (H) - C {H) - 0 cf 3 H -CF 2 CH 2 CH 2 CH 2 - C (H) - C (H) - 0 CHjOCH 2 H -cf 2 ch 2 ch 2 ch 2 - C (H> - C (H> - 0 MeO H -cf 2 ch 2 ch 2 ch 2 - = CÍH) - CÍH) - 0 EtO H -cf 2 ch 2 ch 2 ch 2 - CÍH} - C (H) ~ 0 Pro H -CF 2 CH 2 CfÍ 2 CH 2 - C (H) - C (H) ~ 0 CF 3 CH 2 O H -CF 2 CH 2 CH 2 CH 2 - = C (H} - C (H) - 0 chf 2 ch 2 o H -cf 2 ch 2 ch 2 ch 2 - C (H) - C (H) - 0 iPrO H -cf 2 ch 2 ch 2 ch 2 - C (H) - -C (H} - 0 cPrCH 2 O H -CF 2 CH 2 CH 2 CH 2 - C (H) - C (H) - 0 cPeno H -CF 2 CH 2 CH2CH 2 - C (H) - C (H) - 0 Month H -CFICH 2 CH 2 CH 2 - = C (H) - CÍH) - 0 MeS {0) H -cf 2 ch 2 ch 2 ch 2 - CÍH} - = C (H) - 0 Me $ {0) 2 H -cf 2 ch 2 ch z ch 2 - = C (H) - C (H) - 0 54/100 Table 26 R 1 R 2 R 3 R 4 A 1 A Z n EtS H -ce, ch 2 ch 2 ch 2 - -C (H) - = C (H) - 0 EtS (O) H -CP2CH2CH2CH2- «C (H)“ = C (H) ~ 0 EtS (O) 2 H -CF 2 CH 2 CH2CH 2 - = C (H) - »C (H) - 0 PrS H -cf 2 ch 2 ch 2 ch 2 - = C (H) - = C (H) - 0 PrS (0) H -cf 2 ch 2 ch 2 ch 2 - = C (H) - = C (n) - 0 PrS (0) 2 H -CF 2 CH 2 CH 2 CH 2 - ~ C (H) - = C (H) ~ 0 iPrS H -CF2CH2CH2CH2- = C (H) - 0 iPrS (O) H -CF 2 CH 2 CH 2 CH2- = C (H) - = C (H> - 0 ISP (0) 2 H -CF2CH2CH2CH2- = C (H) - = C (H) ~ 0 cp 3 ch 2 s H -CF2CH2CH2CH2- = C (H) - = C (H) - 0 CHAPTERS H -ÇF2CH2CH2CH2- -C (H> - «C (H) ~ 0 MèHN H -CF 2 CH 2 CH 2 CH 2 - = C (H) - = C (H) ~ 0 Me 2 N H -CF2CK2CH2CH2- —C (H) - = C (H) - 0 Me (iPr) M H -cf 2 ch 2 ch 2 ch 2 - = C (H) - = C (H) - 0 F H -CF2CH2CH2O- = C (H> - = C (H) - 0 Cl H -CF2CH2CH2O- -C (H} ~ = C (H) - 0 Br R - CF2CH2CH2O- = C (H> - = C (H) - 0 I H -cf 2 ch 2 ch 2 o- = C (H) - = C (H) - 0 Me H -CF 2 CH 2 CH2O ' = C (H) - = C (H) - 0 Et H -cf 2 ch 2 ch 2 o- = C (H) - = C (H) - 0 Pr H -CF2CH2CH2O- = C (H) - = C (H) - 0 cPr H -CF 2 CH 2 CH 2 0- -C (H) - = C (H> - 0 cf 3 H -CF2CH2CH2O- = C (H) ~ = C (H> - 0 CH3OCH2 H -cf 2 ch 2 ch 2 o- = C (H) - = C (H) - 0 55/100 Table 27 R 1 R 2 R 3 R 4 A 1 A 2 n MeO H -cf 2 ch 2 ch 2 o- = C (H) - = C (H) - 0 EtO H -CF2CH2CH2O- = C (H) - -C (H) - 0 Pro H -cf 2 ch 2 ch 2 o- —C (HJ- = C (H) - 0 cf 3 ch 2 o H -cf 2 ch 2 ch 2 o- = C (H) - = C (H) - 0 CHF2CH2O K -cf 2 ch 2 ch 2 o- = C (H) - = C (H) - 0 OWN K -CF2CH2CH2O- = C (H} - = C (H) - 0 cPrCH 3 o H -CF2CH2CH2O- = C (H) - = C {H) - 0 cPen.0 H -CF2CH2CH2O- = C (H) - = C (H) - 0 Month H -cf 2 ch 2 ch 2 o ~ = C (H) - = C (H> - 0 MeS {0) H -cf 2 ch 2 ch 2 o- = C (H) ~ = C (H) - 0 KfeS (0) 2 H -CF 2 CH z CH 2 0 “ = C (H) - = C (H) - 0 EtS H - cf 2 ch 2 ch 2 0- = C (H) - = C (H) - 0 EtS (0) H -CF £ CH 2 CH 2 0- = C {H) - = C (H) - 0 EtS (0) 2 H -CF 2 CH2GH 2 O- = C (H) - = C (K) - 0 PrS H -CF2CH2CH2O- «C (H) ~ = C {H) - 0 PrS (0) H -cf 2 ch 2 ch 2 o- = C (H) - = C (H) - 0 PrS (O> 2 H -CF 2 CK 2 CH 2 O- = C (H) - = C <H) - 0 iPrs H “CF2CH2CH2O- = CÍH) - 0 iPrS (O) R -CF 2 CH 2 CH 2 O “ = C (H) - = C (H) - 0 iPrS {0) 2 H -CF2CH2CH2O = C (H) - —Ç (H) “ 0 CF3CH2S H -CF2CH2CH2O- = C (H) - 0 CHF2CH2S H -cf 2 ch 2 ch 2 o- = C (H) - = C (H) - 0 MeHN H -cf 2 ch 2 ch 2 o- = C (H) - = C (H) - 0 Month 3 N H -cf 2 ch 2 ch 2 o- = C [H> - = C (H) - 0 56/100 Table 28 R 1 R 2 R 3 R 4 A 1 A 2 n Me (iPr) N H -CF2CH2CH2O- «C (H) - «C (H) - 0 F H H cf 3 -C (H) - = C (H) - 0 Cl H H = C (H) - = C (H) - 0 Br H H cf 3 = C (H) - = C (HJ- 0 I H H CF 3 ~ C CH) - = C (H} - 0 Me H H CFs = C (H) - —C (H} “ 0 Et H H cf 3 = C (H) ~ = C (H) - 0 Pr H H CF S = C (B) ~ = C (H) - 0 cPr H H CF 3 = C (H) - ~ C {H) - 0 CFs H H CF 3 = C (Hey> - 0 CH5OCH2 H H CF 3 = C (H> - = C (HJ- 0 MeO H H cf 3 = C (H) ~ = C CH) - 0 EtO H H cf 3 = C {H) - -C (H) - 0 Pro H H CF 3 = C <H) - = C (H) - 0 CF3CH2O H H CF 3 -C (H) - -C (H) - 0 CHF2CH2O s H CF 3 = C (H) - · —C (H) - 0 iPrO H H CFs C (H> - = C (H) - 0 cPrCH 2 0 H H CFs = C (H) - = C (n) - 0 cPen.0 H H CF 3 ~ C (H) - = C (H) - 0 Month H H cf 3 = C {H) - = C (H) - 0 MeS (0) H H cf 3 »C <H) - 0 MeS (O) z H H CFs = C (H) ~ -C (H} - 0 EtS H H CFs = C (H) ~ D EtS (0) H H CFs = C (H) ~ = C (H) - 0 57/100 Table 29 R 1 R 2 R 3 R * A 1 A 2 n EtS (0) z H H cf 3 = CÍH) ~ = C (H) " 0 PrS H H cf 3 = C (H) - ~ C (H) “ 0 PrS (0) H H cf 3 = C (H) - = C (H} - 0 PrS (0) 2 H H cf 3 = C (H) " —C (H) ~ 0 iPrS H H cf 3 = C (H) - —C (H) - 0 iPrS (0) H H cf 3 = C (H) - = C (H) - 0 iPrS (0) 2 H H cf 3 = C (H) - —C (H) - 0 CF 3 CH 2 S H H CF a = C (H) - = C (H) - 0 CHF 2 CH 2 S H H cf 3 = C (H) - = C (H) - 0 MeHN H H cf 3 = C (H) - = C (H) - 0 Mô 2 N H H cf 3 = C (H) - = C (H) - 0 Me (iPr) N H H cf 3 -C (H) ~ = C (H) - 0 CH 3 C (O) NH H H cf 3 = C <H) - -C (H) ~ 0 MâOC (O) NH H H cf 3 = C (H) - = C (H) ~ 0 HC (O) H H cf 3 = C (H> - = C (H) - 0 CH 3 C (O) H H CFí -C (H} - = C (H) - 0 HC (NOMe) H H CF â = C (H) - = C (H) - 0 CHsC (NOMe) H H cf 3 = C (H) - = C (H) - 0 Ph H H CF 3 -C (K) - —C (H} - 0 2-Py H H cf 3 = C (H) - = C (H) - 0 3-Fy H H cf 3 = C (H) - = C (H) - 0 4-Fy H H CF 3 = C (H) - = C (H) - 0 1-Tz H H cf 3 = C (H) - = C (H) ~ 0 1-Pz H H cf 3 = C (HJ- 0 58/100 Table 30 R 1 R 2 R 3 R 4 A 1 A 2 n F H H CF S = c (H) - = C [H) - 1 Cl H H cf 3= C (H) - 1 Br H H cf 3 = C (H) - = C (H) - 1 I H H cf 3 —C (H) - —C (H) - 1 Me H H cf 3 = C (B> - —C (H) - 1 Et H H CF 3 = C (H) - = C (H) - 1 Pr H H cf 3 = C (H) - = C (H) - 1 cPr H H cf 3 = C (H) - "C <H) - 1 cf 3 H H cf 3 = C (H} - = C {H) - 1 ch 3 och 2 H H CFs = C (H) - = C (H) - 1 MeO H H cf 3 = C (H) - = C (H) - 1 EtO H H CFs = C (H) - -C (H) - 1 Pro H H cf 3 "C (H) ~ = C (H) - 1 CF 3 CH 2 O H H cf 3 —C (H) - = C (H) - 1 CHF5CH2O H H cf 3 = C (H) - = C (H> - 1 iPrO H H cf 3 = C (H) - = C (H) - 1 Ph H H cf 3 = C (H) - -C (H} ’ 1 F H H cf 3 wC (H) - N 0 Cl K H cf 3 = C {H) - N 0 Br H H cf 3 = C (H) - N 0 I H , H CFs = C (H) - N 0 Me H H cf 3N 0 Et H H CF 3N 0 Pr H H CF 3 = C (H) - N 0 59/100 Table 31 R 1 R 2 R 3 R 4 a l Ά 2 n cFr H H cr 3 = C (H) - N 0 cf 3 H H cf 3 -C (H) - N 0 ch 3 och 2 H H cf 5 = C (H) - K 0 MeO H H cf 3 -C (H) - N 0 EtO H H cf 3 = C (HH N 0 PtO H H cf 3 -C (H) - N 0 CF3CK2O H H cf 3 = C (H) ~ N 0 CHF 2 CH 2 O you H cf 3 = C (H5 - tt 0 iPrO H H CFs = C (H) - N 0 cPrCi ^ Ci H H CFs = C (H} - N 0 cPenO H H CF 0N 0 Month H H cf 3 = C {H) - N 0 MeS (0) H H cf 3 -C (H) - N 0 MeS (O) 2 H H cf 3 = C {H) ~ K 0 EtS H H cf 3 = C (H) - N 0 EtS (O) H H cf 3 = C (H) ~ N 0 Et $ (0) 2 H H cf 3 "CÇH> ~ N 0 PrS H H cf 3 = C (H) - N 0 PrS (0) H you cf 3 = C (H) - N 0 PrS (O) 2 H Pr * * cf 3 = CÍH> - N 0 iPrS H H cf 3 —C (H> - N 0 iPrS {0) H H cf 3 —C (H) - N 0 ÍPrS {O} 2 H H cf 3 = C (H) - M 0 CF3CH2S H H cf 3 = C (H) - N 0, 60/100 Table 32 R 1 R z R 3 R 4 A 1n CHF 2 CH 2 S H H CF3 «C (H) - N 0 MeHN H H cf 3 = C (H) - N 0 Me 2 N H H CFg = C (H) - N 0 Me (iPr) N H H CFg = C {H) - N 0 Ph H H CFg K 0 2-Py H H CFg = C (H) - K 0 3-Fy H H CFg = C (H) ~ M 0 4-Py H H cf 3 = C (H) - K 0 1-Tz H H CF a = C (H) - N 0 1-Pz H H CFg = C (H) - N 0 F H H CFg N = C (H) - 0 Cl H H CFg N = C (H) - 0 BX H H CFg TJ = C (H) - 0 I H H CFg N = C (H) - 0 Me H H CFg N = C (H) - 0 Et H H CFg N = C (H) - 0 Pr H H CFg H -C (H) - 0 CPX H H CFg N = C (H) - 0 CFg H H CFg N = C (H) - 0 CH 3 OCHj2 H H cf 3 N = C (H) - 0 MeO H H CFg N = C (H) - 0 EtO H H CFg N «C (H) - 0 Pro H H cf 3 N -C (H) - 0 CF3CH2O H H CFg N = C (H> - 0 61/100 Table 33 R 1 R 2 R 3 R 4 A 1 A 2 n CHF 2 CH 2 O R H cf 3 N = C (fl) - 0 iPrO H H cf 3 N = C (H) - 0 ePrCH 2 O H H gf 3 N 0 cPenO H H cf 3 N = C (H) - 0 Month H H cf 3 N = C (H) - 0 MeS (0) H H cf 3 N = C (H) - 0 MeS (0) z H H ce 3 N -C (H) - 0 EtS H H CFg N = C (H) - 0 ÊtS (O) H H CFs • N —C (HJ- 0 EtS (05 2 H H cf 3 N = C (Ή) - 0 PrS H H cf 3 N = C (H) - 0 ÈrSÇO) H H CFs N = CÍH) ~ 0 PrS (O) 2 H H cf 3 N = C (Ή) - 0 iPrS H H cf 3 N = C (H) - 0 iPrS (0) H H cf 3 N = c (H5- 0 iPrS (0) z H H cf 3 N = C (H) - 0 cf 3 ch 2 s H H cf 3 N —0 (H) - 0 chf 2 ch 2 s H H cf 3 N = C (H) ~ 0 MeHN H H cf 3 N = C (H) - 0 Me 2 N H H cf 5 N = C (H) - 0 Me (iPr) N H H CFa N -C (HJ- 0 Ph H H CF 3 N = C (H) - 0 2-Py H H cf 3 N = C (H) - 0 3-Py H H cf 3 N = C (H) - 0 62/100 Table 34 R 1 R 2 R 3 R 4 A 1 A 2 n 4-Ργ H H cf 3 N = C (H) - 0 1-Tz H H cf 3 N = C (H> - 0 1-Pz H H cf 3 N = C (H) - 0 F H H cf 3 o = C (H3 ~ —C (H) - 0 Cl H H cf 3 o = C (H) - = C (H) - 0 Br H H cf 3 o C (H) - = C (H) - 0 I H H cf 3 o —C (H) - 0 Me H H cf 3 o = C (H) - = C {H) ~ 0 Et H H CFsO = C (H) - = C (H) - 0 Pr H H cf 3 o = C (H) - —C (H) - 0 cPr H H cf 3 o = C (H) ~ —C (H) - 0 cf 3 H H cf 3 o = C (H> - -C (H) - 0 ch 3 och 3 H H CFsO = C (H> - —C (H) - 0 MeO H H cf 3 o = C (H> - = C (H) - 0 EtO H H cf 3 o = C (H> - —C (H) - ~ 0 Pro H H cf 3 o = C {H) - = C (H} - 0 cf 3 ch 2 o H H cf 3 o = C (H) - = C (H} - 0 chf 2 ch 2 o H H cf 3 o "C (H) - -C (H) - 0 IPrO H H cf 3 o —C (end) - 0 cPrCHsO H H cf 3 o = C (H) - 0 cPenO H H cf 3 o = C (H) - = C (H) - 0 Month H H CF3O = C (H) - = C (H) - 0 MeS (0) H H cf 3 o = C (H) - = C (H) - 0 MeS ¢ 0) 2 H H CF3O = C (H) - = C (H) " 0 63/100 Table 35 R 1 R 2 R 3 R 4 A 1 A 2 n EtS H H cf 3 o -CÍH) - 0 EtS (0) H H cf 3 o = C (H} - 0 EtS (O) z H H cf 3 o = C (H) ~ = CCHS - 0 PrS H H cf 3 o = C (H) - = C (HH 0 PrS (0) H H cf 3 o C (H} - = C (H> - 0 PrS (0) 2 H H cf 3 ü = C (H) ~ 0 iPrS H H cf 3 o = C (H) - = C (H) ~ 0 iPrS (0) H H CF S O = C (H) ~ = C (H) - 0 iPrS (0) 2 H H cf 3 o = C (H) - = C (fi) - 0 cf 3 ch 2 s H H cf 3 o = C (H) - = C (H) - 0 chf 2 ch s H H cf 3 o = C (H) - = C (H) - 0 MeHN H H cf 3 o = C (H) - 0 Me 2 N H H cf 3 o = C (H) - —C (H) - 0 Me (iPr) ÍJ H H cf 3 o -C (H) - = C (H5 - 0 Ph faith H cf 3 o = C (H) - 0 2-Py H H cf 3 o = C (H) - 0 3-Py H H cf 3 o = C (H) ~ = C (H) - 0 4-Py H H cf 3 o = C (H) - = C {H) - 0 1-TZ H H cf 3 o -C (H} - = C (H) - 0 1-Pz H H cf 3 o -G {H) - = C (H) - 0 F H R CFgO = C (H) - = C (H) - 1 Cl H H cf 3 o = C (H) - -C (H) - 1 Br H H cf 3 o = C (H) - = C (H} ~ 1 1 H H cf 3 o = C {H) - = C (H> - 1 64/100 Table 36 R 1 R 2 R 3 R 4 A 1 A z n Me H H CFgO = C (H) - = C (H) - 1 Et H H CF 3 O = C (H) " = C (H) - 1 Pr H H cf 3 o = C (H) ~ = C (n) ~ 1 cPr H H CF 3 O = C (H) - 1 cf 3 H H cf 3 o = C (H) - = C (H) - 1 ch 3 och 2 H H cf 3 o = C (H) - = C (H) - 1 MeO H H cf 3 o 1 EtO H H CF3O -C (H) - 1 Pro H H CF3O C (H> - = C (H) - 1 CF3CH2O H H CF3O = C (H> - = C (H) - 1 CHF 2 CH 2 O H H CF3O -C (f) ~ ~ C (H) - 1 iPro H H cf 3 0 = C (H) - = C (H) - 1 Ph H H cf 2 o = C (H) - = C (HH 1 F H H cf 3 s = C (H) - = C (H) - 0 Cl H H cf 3 s —C (H) - = C (H) - 0 Br H H cf 3 s = C (H) - = C (H) - 0 I H H cf 3 s = C (H) - 0 Me H H cf 3 s = C ÍH) - = C (n) - 0 Et H H cf 3 s = C (H) - = C (H) - 0 Pr H H cf 3 s = C (H) - 0 cPr H H çf 3 s —C (H) - = C (H) - 0 cf 3 H H cf 3 s —C (fí) “ = C (H) - 0 CH3OCH2 H H cf 3 s = C (H) - = C {H) - 0 MeO H H cf 3 s 0 65/100 Table 37 R 1 R a R 3 R 4 A 1 A 2 Ώ EtO H H cf 3 s -C (H) - -C (H) - 0 Pro H H CF 3 S = C (H) - —C (H) - 0 cf 3 ch 2 o H H cf 3 s = C (H) - = CÍH) - 0 CHF2CH2O H H CF3S = C (H) - -C (H) - 0 iPrO H H CF3S C (H) ~ = C (H) - 0 CFrCHjO H H CF3S = C (H) - = C (H) - 0 cPenO H H cf 3 s = C (H) - = C (H) - 0 Month H H cf 3 s = C (H) - = C (H) - ΰ MeS (0) H H cf 3 s = C (H> - = C (H) - 0 MeS (0) 2 H faith cf 3 s = C (H) - 0 EtS H H cf 3 s = C (H) - —C (H) - 0 EtS (O) H H cf 3 s = C (H) - = C (H) - 0 EtS (O) 2 K H cf 3 s = C (H) - = C (H) - 0 PrS H H CF3S = C (H) ~ = C (H) ~ 0 PrS (O) H H CF3S <= C (fin) “ = C (H) ™ 0 PrS (O) 2 H H cf 3 s -C (H) - = C (K) - 0 iPrS H H cf 3 s = C (H) - = C (H) - 0 iPrS (0) H H cf 3 s = C (H) - = C (H) - 0 iPrS (OJs H faith CF to S -CÍH) - = C (H) - 0 CF 3 CH 2 S H H CF3S «C (K)" -C (H) - 0 chf 2 ch 2 s H H cf 3 s = C (H) - -C (H) - 0 MeRN H H cf 3 s = C (H) - = C (H) - 0 Me 2 N H AND cf 3 s = C (H) - = C (H5 - 0 1 Me (iPr) N H H cf 3 s = C (H) - = C (H} - 0 Table 38 R 1 R z R 3 R 4 A 1 A 2 n Ph H H CF3S = C (H) - = C (H) - 0 2-Py H H CF3S = C (H> - = C (R} - 0 3-Py H H cf 3 s = C (H) - = C (H) - 0 4-Py H H cf 3 s = C (H) - = C (H) ’ 0 1-Tz H H cf 3 s = C (H) - = C (H) ~ 0 1-Pz H H cf 3 s = C (H) ~ = C (H) - 0 The arthropod pest control composition of the present invention comprises the present compound and an inert vehicle. The arthropod pest control composition of the present invention is, in general, a formulation obtained by mixing the present compound and a solid vehicle, liquid vehicle, the gaseous vehicle and / or bait (material based on poisonous bait) and 66/100 others, and if necessary, adding a surfactant, and other formulation aids. Examples of the formulation include an oil solution, an emulsifiable concentrate, a dustable formulation, an intumescible powder, a granule, a powder and a microcapsule. These formulations are processed into bait or poisonous foil and used in some cases. The arthropod pest control composition of the present invention usually contains the present compound in an amount of 0.01 to 95% by weight. Examples of the solid carrier used in the manufacture of a formulation include fine powders or granular materials made of clay (kaolin clay, diatomaceous earth, bentonite, Fubasami clay, acid clay and others), synthetic silicon oxide, talc, ceramics, other inorganic minerals (sericite, quartz, sulfur, activated carbon, calcium carbonate, etc.), chemical fertilizers (ammonium sulfate, ammonium nitrate, ammonium chloride, etc.), and others. Examples of the liquid carrier include water, .15 alcohols (methanol, ethanol, 2-propanol, ethylene glycol, etc.), ketones (acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, etc.), aromatic hydrocarbons ( toluene, xylene, ethylbenzene, methylnaphthalene, etc.), aliphatic hydrocarbons (hexane, cyclohexane, kerosene, light oil, etc.), esters (ethyl acetate, butyl acetate, etc.), nitriles (acetonitrile, isobutyronitrile, etc. ), ethers (ethylene glycol dimethyl ether, diisopropyl ether, 1,4-dioxane, tetrahydrofuran, etc.), acid amide (Ν, Ν-dimethylformamide, N, Ndimethylacetamide, etc.), halogenated hydrocarbons (dichloromethane, trichloroethane, etc.), dimethyl sulfoxide and vegetable oils (soybean oil, cottonseed oil, etc.). Examples of the gaseous vehicle include fluorocarbon, butane gas, LPG (liquefied petroleum gas), dimethyl ether, and carbon dioxide. Examples of the surfactant include alkyl sulfate ester salts, alkyl sulfonate salts, alkyl aryl sulfonate salts, alkyl aryl ethers and polyoxyethylene compounds thereof, polyethylene glycol ethers, polyhydric alcohol esters, and alcohol derivatives of sugar. The other formulation aids include fixing agents, dispersing agents, stabilizers and others, and specific examples of 67/100 same include casein, gelatin, saccharides (starch, gum arabic, cellulose derivatives, alginic acid, etc.), lignin derivatives, synthetic water-soluble polymers poly (vinyl alcohol), polyvinyl pyrrolidone, poly (acrylic acids) , etc.), RAF (acid isopropyl phosphate), BHT (2,6-di-tert-butyl-4methylphenol), BHA (a mixture of 2-tert-butyl-4-methoxyphenol and 3-tert-butyl- 4methoxyphenol), mineral oils, fatty acids and fatty esters. Examples of the poison-based bait material include bait components such as cereal flour, vegetable oil, sugar and crystalline cellulose. In poisonous bait, if necessary, an antioxidant such as dibutylhydroxytoluene and nordihydroguaiaretic acid, a preservative such as dehydroacetic acid, an aversive agent to prevent accidental ingestion such as a pepper powder, an attractive harmful insect fragrance such as a cheese fragrance, onion fragrance and peanut oil are added. The arthropod pest control composition of the present invention is used by applying directly to arthropod pests and / or areas where arthropod pests live (nest, plant body, soil and others). In the case of controlling parasitic arthropod pests in a cultivation plant, for example, the arthropod pest control composition of the present invention is sprayed on the above-ground parts of the cultivation plant, or the arthropod pest control composition of the present invention. is injected at the foot of the plant, and others. When the arthropod pest control composition of the present invention is used for the control of arthropod pests in the field of agroforestry, its amount of application is usually 0.1 to 1000 g in terms of the amount of the present compound per 1000 m 2 . When the arthropod pest control composition of the present invention is formulated in an emulsifiable concentrate, flowable formulation, swelling powder, microcapsule and others, the composition is diluted with water so that the concentration of the present compound is usually 1 to 10,000 ppm and sprayed . When the arthropod pest control composition of the present invention is formulated in a solution of oil, granules, powder and others, the composition is 68/100 usually used as is. When the arthropod pest control composition of the present invention is used for the control of arthropod pests in the field of epidemic prevention, its amount of application is usually 0.01 to 1000 mg in terms of the amount of the present compound per 1 m 2 of the area of application when treated on a surface, and usually 0.01 to 500 mg in terms of the amount of the present compound per 1 m 3 of the application space when treated in a space. When the arthropod pest control composition of the present invention is formulated in an emulsifiable concentrate, flowable formulation, swelling powder, microcapsule and others, the composition is diluted with water so that the concentration of the present compound is usually 0.1 to 1000 ppm and applied. When the arthropod pest control composition of the present invention is formulated in a solution of oil, aerosol, smoking agent, poisonous bait and the like, the composition is usually used as is. The arthropod pest control composition of the present invention may contain insecticide active ingredients, acaricide active ingredients, nematicide active ingredients, fungicide active ingredients, herbicide active ingredients and / or plant growth regulator active ingredients, in addition to present compound. Examples of the active ingredients in insecticides include the following components: (1) Organic phosphorus compounds: Aacefate, aluminum phosphide, butathiophes, cadusaphos, chlorethoxyphos, chlorfenvinfos, chlorpyrifos, chlorpyrifos-methyl, cyanophos (CYAP), diazinon, DCIP (dichlorodiisopropyl ether), diclofention (EPP), dichlorides (DDVP), dim, dichloride, dichloride, dichloride, , etion, etoprofos, etrinfos, fention (MPP), fenitrotion (MEP), fostiazato, formotion, hydrogen phosphide, isofenfos, isoxation, malation, mesulfenfos, metidation (DMT2), monocrotofos, naled (BRP), oxidoprofos (ESP), paration, fosalone, fosmet (PMP), pirimiphos-methyl, pyridafention, quinalfos, fentoatp (PAP), profenofos, propafos, protiofos, pirachlorfos, salition, sulprofos, tebupirinfos, temefos, tetrachlorvinfos, terbufos, tiometon, 69/100 triclorpnon (DEP), vamidotion, forato, cadusafos, and others; (2) Carbamate compounds: Alanicarb, bendiocarb, benfuracarb, 8PMC, carbaryl, carbofuran, earbossulfan, cloetocarb, etiefencarb, fenobucarb, fenotiocarb, fenoxicarb, furatiocarb, isoprocarb (MIPC), metolcarb, methyl, motiocarb, NAC, oxam, pirac, pirac, NAC, oxam tiodicarb, xylylcarb, aldicarb, and others; (3) Pyrethroid compounds: Acrinatrine, aletrine, benflutrin, beta-cyfluthrin, bifentrine, cyoloprotrin, cyfluthrin, cyhalothrin, cypermethrin, deltamethrin, sphenolvalerate, βίοι 0 fenprox, fenpropatrin, fenvalerate, flucitrinate, flufetrine, flufetretrin, flufetretrin, flufenetroxin, flufetrin, flufetretrin, flufetrin, flufetretrin, flufetretrin, flufetretrin, flufetretrin, flufetrin, flufetretrin, flufetretrin, flufetretrin, flufetretrin, flufetretrin, flufetretrin, flufetretrin, flufetretrine, flufetrine, fletretrin, flufetrin, flufetretrine. resmethrin, sigma-cypermethrin, silafluofen, toflutrin, tralometrine, transflutrin, tetramethrin, phenothrine, kyphenothrin, alpha-cipormetrin, zeta-cypermethrin, lambdacialotrin, gamma-cyalothrin, furamethrin, tau-fluvalin, - 2,3,5,6-tetrafluoro-4- (methoxymethyl) benzyl, (EZ) - (1RS, 3RS; 1RS, 35R) -2,2-dimethyl-3-prop-1enylcyclopropane-carboxylate, (EZ) - (1RS, 3RS ; 1, 2, 3SR) -2,2-dimethyl-3-prop-1-enylcyclopropane-carboxylate 2,3,5,6-tetrafluoro-4-methylbenzyl, (1 RS, 3RS; 1 RS, 3SR) -2, 2,3,5,6-tetrafluoro-420 (motoxymethyl) benzyl 2-dimethyl-3- (2methyl-1-propenyl) cyclopropane-carboxylate and others; (4) Nereistoxin compounds: Cartap, bensultap, tiiciclam, monossultap, bisaltap, and others; (5) Neonicotinoid compounds: Imidacloprid, nitenpiram, acetamiprid, thiamethoxam, thiacloprid, di25 notefuran, clothianidin, and others; (6) Benzoylurea compounds: Chlorfluazuron, bistrifluron, diafentiuron, diflubenzuron, fluazuron, flucicloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron, triflumuron, triazuron, and others; (7) Phenylpyrazole compounds: Acatoprol, etiprol, fipronil, vaniliprol, pyriprol, pirafluprol, and others; (8) Bt Toxin: 70/100 Live spores derived from the crystal toxins produced from Bacillus turingiesis and a mixture thereof; (9) Hydrazine compounds: Chromafenozide, halofenozide, methoxyfenozide, tebufenozide, and others; (10) Organic chlorine compounds: Aldrin, dieldrin, dienochlor, endosulfan, methoxychlor, and others; (11) Others: Machine oil, nicotine-sulfate; avermectin-B, bromopropylate, buprofezin, chlorfenapyr, cyantraniliprol, circmazine, DD- (1,3dichloropropene), emamectin-benzoate, phenazaquin, flupirazofos, hydroprene, methoprene, indoxacarb, methoxadyrine, pyrethoxidine, pyrethoxy, pyrethoxy, pyrethoxy, pyrethoxy, pyrethoxy, pyrethoxy, pyrethoxy, pyrethoxidine, pyrethoxidine triazamate, flubendiamide, lepimectin, arsenic acid, benclothiaz, calcium cyanamide, calcium polysulfide, chlordane, DDT, DSP, flufenerin, flonicamid, flurinfen, formethanate, metamamonium, metam-sodium, methyl bromide, potassium oleate , sulfoxaflor, sulfur, metaflumizone, spirotetramat, pyrifluquinazone, espinetoram, chlorantraniliprol, tralopyril, any compound represented by the following formula (A): where, R a represents Me, Cl, Br or F; R * represents F, Cl, Br, haloalkyl, or C1-C4 haloalkoxy; R c represents F, Cl or Br; R d represents a C-1-C4 alkyl, a C1-C4 alkenyl, C3-C4 alkynyl or C3-C5 cycloalkylalkyl optionally substituted by H, one or more halogen atoms; CN; SMe; S (O) Me; S (O) 2 Me and OMe; R e represents H or Me; R f represents H, F or Cl; and R 9 represents H, F or Cl. Examples of the active ingredients of acaricides include the following 71/100 components: acequinocila, amitraz, benzoximate, biphenate, bromopropylate, quinomethionate, chlorobenzylate, CPCBS (chlorfenson), clofentezine, ciflumetofen, queltane (dicofol), ethoxyzol, phenbutatin oxide, phenothiocarb, phenoxyoxy, propoxyoxy, fluoxyoxy, fluoxyoxy, fluoxyoxy , pyridaben, pyrimidifene, tebufenpirad, tetradifon, spirocliclofen, spiromesifene, apirotetramat, amidoflumat and cyienopirafen. Examples of the active ingredients in nematicides include the following components: DCIP, fosthiazate, levamisole, methylisothiocyanate, morantel tartrate and imiciafos. Examples of the active ingredients of fungicides include the following components: azole compounds such as propiconazole, proticonazole, triadimenol, prochloraz, penconazole, tebuconazole, flusilazole, diniconazole, bromuconazole, epoxiconazole, diphenoconazole, cyproconazole, metconazole, triflumizole, tetraconazol, hexanol, trichloromethane, trichlazole, trichlazole ; cyclic amine compounds such as fenpropimorf, tridemorf and fenpropidina; benzimidazole compounds such as carbendezin, benomyl, thiabendazole and thiophanate-methyl; procymidone, ciprodinil, pyrimethanil, dictofencarb, tiuram, fluazinam, mancozeb, iprodiona, vinclozolin, chlorotalonil, captan, mepanipyrim, fenpiclonil, fludioxonil, diclofluanid, folpet, cresoxim-metil, azoxoxystrobin, pyroxystrobin, pyridine, trifl spiroxamine, quinoxifene, fenexamid, famoxadone, fenamidone, zoxamide, etaboxam, amissulbrom, iprovalicarb, bentiavalicarb, ciazofamid, mandipropamid, boscalid, pentiopirad, motrafenone, fluopiran, bixafid, and ciflufenquin. Examples of the herbicide active ingredients include the following components: 72/100 (1) Phenoxy-fatty acid compounds 2,4-PA, MCP, MCPB, phenothiol, mecoprop, fluroxypyr, triclopyr, cio meprop, naproanilide and others; (2) Benzoic acid compounds 2,3,6-TBA, dicamba, clopiralid, picloram, aminopiralid, quinclora co, quinmeraco and others; (3) Urea compounds diuron, linuron, chlortoluron, isoproturon, fluometuron, isouron, te butiuron, metabenztiazuron, cumiluron, daimuron, methyl-daimuron and others; (4) Triazine compounds atrazine, ametorin, cyanazine, simazine, propazine, symmetry dimetamethrin, promethrin, metribuzin, triaziflam, indaziflam and others; (5) Paraquat, diquat and other bipyridinium compounds; (6) Hydroxybenzonitrile bromoxynil, ioxynil and others; (7) Dinimaroaniline compounds pendimatalina, prodiamina, trifluralina and others; (8) Amiprofos-methyl organophosphorus compounds, butamiphos, bensulide, piperophos, anilophos, glyphosate, glufosinate, glufosinate-P, bialafos and others; (9) Carbamate di-alate, tri-alate, EPTC, butylate, bentiocarb, esprocarb, molinate, dimepiperate, swep, chlorprofam, fenmedipham, phenisofam, pyributicarb, asu · iam and others compounds; (10) Propanyl acid amide compounds, propizamide, bromobutide, etobenzanid and others; (11) Compounds of chloroacetanilide acetochlor, alachlor, butachlor, dimethenamid, prrapachlor, metazachlor metolachlor, pretilachlor, tenilchlor, petoxamid and others; (12) Diphenylether compounds acifluorfon-sodium, bifenox, oxyfluorfen, lactofen, fomesafen, cio73 / 100 methoxyinil, aclonifen and others; (13) Cyclic imide compounds ozadiazon, cinidon-ethyl, carfentrazone-ethyl, surfentrazone, flumichlorac-pentyl, flumioxazin, piraflufen-ethyl, oxadiargyl, pentoxazone, flutiacet-methyl, butafenacil, benzfendizone, and benzufendone; (14) Compounds of pyrazole benzofonap, pyrazolate, pyrazuxifen, topramezone, pyrasulfotol and others; (15) Trichetone compounds isoxaflutol, benzobicyclon, sulcotrione, mesotrione, tembotrione, tefuriltrione, bicyclopyrone and others; (16) Aryloxyphenoxypropionic acid compounds clodinafop-propargyl, cyhalofop-butyl, diclofop-methyl, phenoxaprop-ethyl, fluazifop-butyl, haloxifop-methyl, quizalofop-ethyl, metamifop and others; (17) Compounds of sodium thionoxime alloxidim, setoxidim, butroxidim, cletodim, cloproxidim, cicloxidim, tepraloxidim, tralcoxidim, profoxidim and others; (18) Sulfonylurea compounds chlorsulfuron, sulfemeturon-methyl, metsulfuron-methyl, chlorimuronethyl, tribenuron-methyl, triasulfuron, bensulfuron-methyl, tifensulfuron-methyl, pyrazosulfuron-ethyl, primisulfuron-methylsulfuron, aminosulfuron, aminosulfon-sulfuron, halosulfuron-methyl, prosulfuron, etametsulfuron-methyl, triflussulfuron-methyl, flazasulfuron, cyclosulfamuron, flupirsulfuron, sulfosulfuron, azinsulfuron, ethoxysulfuron, oxulfulfuron, iodosulfuron-methylsulfon, methanesulfon, methanesulfonyl, trisulfonur metazosulfuron, and others: (19) Imidazolinone compounds imazametabenz-methyl, imazametapyr, imazamox, imazapyr, imazaquin, imazetapyr and others; 74/100 (20) Sulfonamide compounds flumetsulam, metosulam, diolossulam, florasulam, chloransulammethyl, penoxsulam, pyroxsulam and others; (21) Pyrimidinyloxybenzoic acid compounds piritiobac-sodium, bispyribac-sodium, pyriminobac-methyl, pyribenzoxim, pyriftalid, pyrimisulfan and others; (22) Other bentazon, bromacil, teridadil, chlortiamid, isoxaben, dinoseb, amitrol, cinmetilin, tridifan, dalapon, diflufenzopyr-sodium, dithiopir, tiazopir, flucarbazone-sodium, propoxycarbazone-sodium, mefenacet, fufentram, flufen, oxazyclomefone, benfuresate, ACN, pyridate, chloridazon, norflurazon, flurtamone, diflufenican, picolinafen, beflubutamid, clomazone, amicarbazone, pinoxaden, pyraclonil, pirexassulfone, tiencarbazonamethyl, aminocyclone, aminocyclone Examples of the active ingredients of plant growth regulators include the following compounds: himexazole, paclobutrazol, uniconazole-P, inabenfide, proexadionacalcium, aviglycine, 1-naphthylacetamide (naphthalene acetamide), abscisic acid, indolebutyric acid, eticlozate, etefon, cloxifenac, clormequat, benzoin, dichlorohydrate, maleic hydrazide, calcium peroxide, mepiquat-chloride and 4-CPA (4-chlorophenoxyacetic acid). Examples of arthropod pests to which the present compound exhibits an effect include harmful insects and harmful mites. Examples of these include the following organisms. Hemiptera: Leafhoppers (Delphacidae) such as small brown leafhoppers (Laodelphax striatellus), brown rice leafhoppers (Nilaparvata lugens), white rice leafhoppers (Sogatella furcifera) and others; leafhoppers (Deltocephalidae) such as green rice leafhopper (Nephotettix cincticeps), green rice leafhopper (Nephotettix virescens), green rice leafhopper (Empoasca onukii) and others; aphids (Aphididae) such as aphid of the 75/100 cotton (Aphis gossypii), green peach aphid (Myzus persicae), cabbage aphid (Brevicoryne brassicae), spire aphid (Aphis spiraecola), potato aphid (Macrosiphum euphorbiae), foxglove aphid (Aulacorthum solani) wild cherry louse (Rhopalosiphum padi), tropical citrus aphid (Toxoptera citricidus), plum floury aphid (Hyalopterus pruni) and others; stink bugs (stink bug) such as green stink bug (Nezara antennata), bean bug (Riptortus clavatus), rice bug (Leptocorisa chinensis), white spot bug (Eysarcoris parvus), bug (Halyomorpha mixed) and others; white flies (Aleyrodidae) such as greenhouse whitefly (Trialeurodes vaporariorum), tomato whitefly (Bemisia tabaci), citrus whitefly (Dialeurodes citri), citrus whitefly (Aleurocanthus spiniferus) and others; scale insects (Coccidae) such as red spot scale (Aonidiella aurantii), San José scale (Comstockaspis perniciosa), flour scale scale (Unaspis citri), red scale (Ceroplastes rubens), Australian scale (Iceryoccusa purchasi) kraunhiae), long tail white scale (Pseudococcus longispinis), white peach scale (Pseudaulacaspis pentagona) and others; lace bug (Tingidae); bedbugs such as Cimex lectularius and others; psyllids (Psyllidae); etc. Lepidoptera: Pyramid moths (Pyralidae) such as rice stem borer (Chilo suppressalis), yellow rice borer (Tryporyza incertulas), rice defoliator (Cnaphalocrocis medinalis), cotton defoliator (Notarcha derogata), Indian moth (Plodia interpunctella), borer Asian corn (Ostrinia furnacalis), kale borer (Hellula undalis), grass grass borer (Pediasia teterrellus) and others; moth moths (Noctuidae) such as common caterpillar (Spodoptera litura), beet cartridge caterpillar (Spodeptera exigua), cartridge caterpillar (Pseudaletia separata), cabbage cartridge caterpillar (Mamestra brassicae), screw caterpillar (Agrotis ipsilon), beet semi-larva (Plusia nigrisigna), Thoricoplusia spp., Heliothis spp .. Helicoverpa spp. and others; white butterflies (Pyeridae) such as borbole76 / 100 cabbage (Pyeris rapae) and others; tortricidae moths (Tortricidae) such as Adoxophyes spp., oriental moth (Grapholita molesta), soybean borer (Leguminivora glycinivorella), azuki bean borer (Matsumurasses azukivora), fruit tortricide (Adoxophyes orana fasciata), minor tortricidae Adoxophyes honmai.), Oriental tea tortricids (Homona magnanima), apple tortricid (Archips fuscocupreanus), apple moth (Cydia pomonella) and others; leaf spot mining caterpillars (Gracillariidae) such as tea defoliator (Caloptilia theivora), apple caterpillar (Phyllonorycter ringoneella) and others; Carposinidae such as the peach moth (Carposina niponensis) and others; lionetid moths (Lyonetiidae) such as Lyonetia ap. and others; Tussock moths (Lymantriidae) such as Lymantria spp., Euproctis spp, and others; iponomeutidae moths (Yponomeutidae) such as crucifer moths (Plutella xylostella) and others; geleleid moths (Gelechiidae) such as pink cottonworm (Pectinophora gossypiella), potato moth (Phthorimaee operculella) and others; tiger and allied moths (Arctiidae) such as autumn borer (Hyphantria cunea) and others; silverfish moths (Tineidae) such as clothes moths (Tinea translucens), clothes moths (Tineola bisselliella) and others; etc. Tisanoptera: Tripods (Thripidae) such as yellow citrus tripods (Western Frankliniella), melon tripods (Thrips palmi), yellow tea tripods (Scirtothrips dorsalis), onion tripods (Thrips tabaci), flower tripods (Frankliniella intonsa) and others, etc. Diptera: Colicles such as common mosquito (Culex pipiens pallens), Culex tritaeniorhynchus, Culex quinquefasciatus and others; Aedes spp. such as yellow fever mosquito (Aedes aegypti), Asian tiger mosquito (Aedes albopictus) and others; Anopheles spp. such as Anopheles sinensis and others; chironomids (Chironomidae); house flies (Muscidee) such as Musca domestica, Muscina stabulans and others; blowflies (Calliphoridae); flesh flies (Sarcophagidae); small house flies (Fanniidae); antomyid flies (Anthomyiidae) such as corn flies (Delia platura), onion flies (Delia antiqua) and others; mining flies (Agromyzidae) such as rice miner fly (Agromyza oryzae), small rice miner fly (Hydrellia griseola), tomato miner fly (Liriomyza sativae), vegetable miner fly (Liriomyza trifolii), pea leaf miner (Chromatomyia horticola) and others; 'drop' fly (Chloropidae) such as rice stalk insect larva (Chlorops oryzae) and others; fruit fly (Tephritidae) such as melon fly (Dacus cucurbitae), Mediterranean fruit fly (Ceratitis capitata) and others; Drosophilidae; 'cordundas' wild flies (Phoridae) such as Megaselia spiracularis and others; sewer flies (Psychodidae) such as Clogmia albipunctata and others; Simuliidae; Tabanidae such as horsefly (Tabanus trigonus) and others; flies from the stables, etc. Coleoptera: Corn root larvae (Diabrotica spp.) Such as corn rootworm larva (Diabrotica virgifera virgifera), corn rootworm larva (Diabrotica undecimpunctata howardi) and others; beetles (Scarabaeidae) such as cupric beetle (Anômala cuprea), soy beetle (Anômala rufocuprea), Japanese beetle (Popillia japonica) and others; weevils such as corn weevil (Sitophilus zeamais), rice water weevil (Lissorhoptrus oryzophilus), azuki bean weevil (Callosobruchus chinensis), rice curculus (Echinocnemus squameus), cotton weevil (Anthonomus grandis), curculionidae venatus) and others; black beetles (Tenebrionidae) such as breadworm (Tenebrio molitor), red flour beetle (Tribolium castaneum) and others; leaf beetles (Chrysomelidae) such as rice leaf beetle (Oulema oryzae), pumpkin leaf beetle (Aulacophera femoralis), striped aphid (Phyllotreta striolata), Colorado potato beetle (Leptinotarsa decemlineata) and others; dermestidae beetles (Dermestidae) such as rugs and carpets (Anthrenus verbasci), leather beetles (Dermestes maculates) and others; wake beetles (Anobiidae) such as the smoke beetle (Lasioderma serricorne) and others; Epilachna tais co78 / 100 mo ladybug (Epilachna vigintioctopunctata) and others; bark beetles (Scolytidae) such as woodworm (Lyctus brunneus), pine beetle (Tomicus piniperda) and others; false woodworms (Bostrychidae); spider beetles (Ptinidae); long-antennaed beetles (Cerambycidae) such as stem borers (Anoplophora malasiaca) and others; pins (Agriotes spp.); Paederus fuscipens, etc. Orthoptera: Migratory locust (Locusta migrativa), mole cricket (Gryllotalpa africana), rice locust (Oxya yezoensis), rice locust (Oxya japonica), Gryllidae, etc. Siphonaptera: Cat flea (Ctenocephalides felis), dog flea (Ctenocephalides canis), human flea (Pulex irritans), rat flea (Xenopsylla cheopis), etc. Anópluros: Human body louse (Pediculus humanus corporis), flat (Phthirus pubis), short-nosed cattle louse (Haematopinus eurysternus), sheep louse (Dalmalinia ovis), pig louse (Haematopinus suis), etc. Hymenoptera: Ants (Formicidae) such as pharaoh ant (Monomorium pharaosis), black ant (Formica fusca japonica), black ant (Ochetellus glaber), Pristomyrmex pungens, Pheidole noda, leaf-cutting ant (Acromyrmex spp.), Fire ant (Solenopsis spp. .) and others; hornets (Vespidae); betylid wasps (Betylidae); saw flies (Tenthredinidae) such as the turnip saw (Athalia rosae), Athalia japonica and others, etc. Blatódeos: German cockroach (Blattella germanica), soot brown cockroach (Periplaneta fuliginosa), American cockroach (Periplaneta americana), Periplaneta brunnea, oriental cockroach (Blatta orientalis) and others; Acarinos: Spider mites (Tetranychidae) such as spider mites 79/100 two spots (Tetranychus urticae), Kanzawa spider mite spider (Tetranychus kanzawai), red citrus mite (Panonychus citri), European red mite (Panonychus ulmi), Oligonychus spp. and others; eriophid mites (Eriophyidae) such as citrus rust mite (Aculops pelekassi), Phyllocoptruta citri, tomato rust mite (Aculops lycopersici), purple tea mite (Calacarus carinatus), purple turpentine mite (Acaphylla theavagrans), Eriophyes chibaensis, purple apple mite (Aculus schlechtendali) and others; tarssonemid mites (Tarsonemidae) such as white mite (Polyphagotarsonemus latus) and others; false mites (Tenuipalpidae) such as Brevipalpus phoenicis and others; Tuckerellidae; ticks (Ixodidae) such as Haemaphysalis longicornis, Haemaphysalis fiava, Dermacentor taiwanicus, Ixodes ovatus, Ixodes persulcatus, black leg tick (Ixodes scapularis), Boophilus microplus, Rhipicephalus sanguineus and others; mites (Acaridae) such as mold mites (Tyrophagus putrescentiae), Tyrophagus similis and others; household dust mites (Pyrogiyphtdae) such as Dermatophagoides farinee, and Dermatophagoides ptrenyssnu and others; cheyletid mites (Cheyletidae) such as Cheyletus eruditus, Cheyletus malaccensis, Cheyletus moorei and others; parasitic mites (Dermanyssidae) such as wild mouse mite (Ornithonyssus bacoti), feather mite (Ornithonyssus sylviarum), red poultry mite (Dermanyssus gallinae) and others; insects (Trombiculidae) such as Leptotrombidium akamushi and others; spiders (Araneae) such as foliage spider (Cheiracanthium japonicum), Australian spider (Latrodectus hasseltii) and others, etc. The arthropod pest control composition of the present invention can be used on agricultural land to cultivate the plantations listed below, and others. Agricultural crops: corn, rice, wheat, barley, rye, oats, sorghum, cotton, soy, peanuts, sarrazin, sugar beet, canola, sunflower, sugar cane, tobacco, etc .; Vegetables: Solanaceae vegetables (eggplant, tomato, green pepper, pepper, potato etc.), Cucurbitaceae vegetables (cucumber, pumpkin, zucchini, watermelon, melon, etc.), Cruciferae vegetables (Japanese radish, turnip, horseradish, cabbage) - turnip, Chinese cabbage, cabbage, brown mustard, broccoli, cauliflower etc.), Compositae vegetables (burdock, chrysanthemum, artichoke, lettuce etc.), Liliaceae vegetables (Welsh onion, onion, garlic, asparagus etc.), ve5 Umbelliferae getais (carrots, parsley, celery, parsnips etc.), Chenopodiaceae vegetables (spinach, chard, etc.), Labiatae vegetables (Japanese basil, mint, basil etc.), strawberry, sweet potato, yam, aracea, etc .; Fruit trees: pomegranate fruits (apple, common pear, Japanese pear, Chinese quince, quince etc.), pevid fruit (peach, plum, nectarine, Japanese plum, cherry, apricot, prune etc.), citrus fruits (Satsuma mandarin, orange, lemon, lime, grapefruit etc.), nuts (chestnut, walnut, hazelnut, almond, pistachio, cashews, macadamia etc.), soft fruits (blueberry, cranberry, blackberry, raspberry etc.), grape , persimmon, olive, loquat, banana, coffee, date, coconut, palm tree, etc .; .15 Different fruit trees: tea, blackberry, flowering trees (rhododendron, camellia, hydrangea, camellia-sasanqua, Japanese anise, Japanese cherry, tulip, myrtle-crepe, fragrant orange oil, etc.), street trees (ash, birch, dogwood, eucalyptus, ginkgo, lilac, maple tree, oak, poplar, judas tree, chinese amber tree, plane tree, Zelkova, Japane20 se arborvitae, fir tree, japanese hemlock, needle-shaped juniper, pine , spruce, yew, elm, Japanese chestnut, etc.), fragrant viburnum, broadleaf podocarp, Japanese cedar, Hinoki cypress, croton, Japanese axis, May flower, etc. Grass; emerald (Japanese grass, mascane grass, etc.), bermuda grass (Cynodon dactylon, etc.), common grass (low grass, Agrostis stolonifera, Agrostis tenuis, etc.), blue grass (dog-hair -decolmo-smooth, hair-of-dog-of-rough-thatched-dog, etc.), fescue (fescue of the meadows, red fescue, fescue-dwarf, etc.), Castilian grass (chaff, perennial grass, etc.) , panasco, grass-of-meadows, etc .; Others: flowering herbs (rose, carnation, chrysanthemum, Eustoma grandiflorum Shinners (prairie gentian), gypsophila, gerbera, marigold, salvia, petunia, verbena, tulip, aster, gentian, lily, pansy, cyclamen, or81 / 100 quidea, lily of the valley, lavender, gouge, ornamental kale, primrose, leaf-blood, gladiolus, catlea, daisy, orchid-cymbidium, begonia, etc.), plants for biofuels (jatropha, safflower, Camelina alyssum, switchgrass grass, eulalia , spotted reed, Great reed grass, kenaf, cassava, willow, algae, etc.), ornamental foliage plants, etc. The plantations described above include genetically modified plantations. EXAMPLES .15 The present invention will be further explained in detail by the Production Examples, Reference Production Examples and Test Examples below, but the present invention is not limited to them. First, the Production Examples are shown for the production of the present compound. Production Example 1 A mixture of 2.3 g of 2-amino-4- (trifluoromethyl) benzenethiol hydrochloride, 1.25 g of 3-fluoroisonicotinaldehyde, 1.29 g of N-ethyldiisopropylamine and 10 ml of DMSO was stirred for 5 hours at 170 ° C. ° C. The reaction mixture was cooled to room temperature. To the reaction mixture, water was added, and the resulting mixture was extracted twice with ethyl acetate. The combined organic layers were washed with water and saturated saline, dried over magnesium sulfate, then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 1.79 g of 2- (3-fluoropixidin-4-yl) -5- (trifluoromethyl) benzothiazole (hereinafter referred to as the present compound 1). The present compound 1 1 H-NMR (CDCb) δ: 8.72 (d, J = 2.4 Hz, 1H), 8.65-8.63 (m, 1H), 8.47-8.45 (m, 1H), 8.34-8.31 (m, 1H), 8.12 (d, J = 8.5 Hz, 1H), 7.73 (dd, J = 8.5, 1.7 Hz, 1H) Production Example 2 2- (3-chloropyridin-4-yl) -5- (trifluoromethyl) benzothiazole (hereinafter, re82 / 100 wounded as the present compound 2) was obtained in the same way as in Production Example 1, except that 3-chloroisonicotinaldehyde was used instead of 3-fluoroisonicotinaldehyde. Cl The present compound 2 1 H-NMR (CDCI 3 ) δ: 8.82 (s, 1H), 8.68 (d, J = 5.1 Hz, 1H), 8,478.45 (m, 1H), 8, 29 (d, J = 5.1 Hz, 1H), 8.12 (d, Hz, 1H), 7.73 (dd, J = 8.5, 1.2 Hz, 1H) Production Example 3 To a mixture of 0.50 g of 2- (3-chloropyridin-4-ii) -5- (trifluoromethyl) benzothiazole and 5 ml of chloroform was added 0.51 g of 70% chloroperbenzoic acid under ice cooling. This mixture was stirred at room temperature for 5 hours. The reaction mixture was diluted with chloroform, and washed sequentially with a 5% aqueous sodium hydroxide solution and saturated saline. The organic layer was dried over magnesium sulfate, then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.43 g of 2- (3chloro-1-oxipyridin-4-yl) -5- (trifluoromethyl) benzothiazole (hereinafter referred to as the present compound 3) . The present compound 3 1 H-NMR (CDCb) δ: 8.45 (d, J = 7.1 Hz, 1H), 8.41-8.39 (m, 2H), 8.21 (dd, J = 7.1, 1.7 Hz, 1H), 8.10 (d, J = 8.3 Hz, 1H), 7.71 (m, 1H) Production Example 4 A mixture of 0.28 g of 2- (3-fluoropyridin-4-yl) -5- (trifluoromethyl) benzothiazole, 0.28 g of potassium carbonate and 3 ml of methanol was refluxed with heating for 1.5 hours. The reaction mixture was cooled to room temperature. To the reaction mixture, water was added, and the resulting mixture was extracted twice with ethyl acetate. The combined organic layers were washed with water and saturated saline, dried over magnesium sulfate, then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 2- (3methoxypyridin-4-yl) -5- (trifluoromethyl) benzothiazole (hereinafter, referred to as the present compound 4). The present compound 4 1 H-NMR (CDCb) δ: 8.58 (s, 1H), 8.47 (d, J = 4.9 Hz, 1H), 8.428.40 (m, 1H), 8.37 (d, J = 4.9 Hz, 1H), 8.09-0.06 (m, 1H), 7.69-7.65 (m, 1H), 4.21 (s, 3H) Production Example 5 A mixture of 0.30 g of 2- (3-fluoropyridin-4-yl) -5- (trifluoromethyl) benzothiazole, 0.14 g of methylmercaptan sodium salt and 3 ml of DME was stirred at room temperature for 20 minutes . To the reaction mixture, water was added, and the resulting mixture was extracted three times with ethyl acetate. The combined organic layers were washed with water and saturated saline, dried over magnesium sulfate, then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 2- [3- (methylthio) pyridin-4-yl] -5- (trifluoromethyl) benzothiazole (hereinafter, referred to as the present compound 5). The present compound 5 1 H-NMR (CDCb) δ: 8.76-8.75 (m, 1H), 8.58 (d, J = 5.1 Hz, 1H), 9.46-8.44 ( m, 1H), 8.10-8.07 (m, 1H), 7.91 (dd, J = 5.1, 0.7 Hz, 1H), 7.73-7.69 (m, 1H) , 2.61 (s, 3H) Production Example 6 2- [3- (ethylthio) pyridin-4-yl] -5- (trifluoromethyl) benzothiazole (hereinafter, re84 / 100 wound as the present compound 6) was obtained in the same manner as in Production Example 5, except that a sodium salt of ethylmercaptan was used instead of the sodium salt of methylmercaptan. The present compound 6 1 H-NMR (CDCIs) δ: 8.72 (s, 1H), 8.56 (d, J = 5.1 Hz, 1H), 8,238.21 (m, 1H), 8.02 (d, J = 5.1 Hz, 1H), 7.77-7.70 (m, 2H), 3.19 (q, J = 7.4 Hz, 2H), 1.48 (t, J = 7.4 Hz, 3H) Production Example 7 To a mixture of 0.65 g of 2- [3- (ethylthio) pyridin-4-yl] -5 (trifluoromethyl) benzothiazole and 5 ml of chloroform was added 0.66 g of 70% m-chloroperbenzoic acid under cooling in ice. This mixture was stirred at 0 ° C for 1 hour. The reaction mixture was diluted with chloroform, and washed sequentially with a 5% aqueous solution of sodium hydroxide and saturated saline. The organic layer was dried over magnesium sulfate, then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.19 g of 2- [3 (ethanesulfonyl) pyridin-4-yl] -5- (trifluoromethyl) benzothiazole (hereinafter referred to as the present compound 7) and 0.35 g of 2- [3- (ethanesulfinyl) pyridin-4-yl] -5 (trifluoromethyl) benzothiazole (hereinafter, referred to as the present compound 8). The present compound 7 1 H-NMR (CDCI 3 ) δ: 9.40 (s, 1H), 9.04 (d, J = 4.9 Hz, 1H), 8,388.36 (m, 1H), 8, 12 (d, J = 8.5 Hz, 1H), 7.77-7.74 (m, 1H), 7.65-7.63 (m, 1H), 3.82 (q, J = 7, 5 Hz, 2H), 1.42 (t, J = 7.4 Hz, 3H) 85/100 The present compound 8 1 H-NMR (CDCfe) δ: 9.46 (s, 1H), 8.93 (d, J = 5.1 Hz, 1H), 8,388.37 (m, 1H), 8.13 (d, J = 8.5 Hz, 1H), 7.79-7.75 (m, 2H), 3.54 (dq, J = 13.2, 7.4 Hz, 1H), 3.13 ( dq, J = 13.2, 7.4 Hz, 1H), 1.50 (t, J = 7.4 Hz, 3H) Production Example 8 A mixture of 0.90 g of 3-amino-5- (trifluoromethyl) -pyridine-2-thiol, 0.58 g of 3-fluoroisonicotyraldehyde and 5 ml of DMSO was stirred at 170 ° C for 2 hours. The reaction mixture was cooled to room temperature, then, to the reaction mixture, water was added, and the resulting mixture was extracted twice with ethyl acetate. The combined organic layers were washed with water and saturated saline, dried over magnesium sulfate, then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.55 g of 2- (3 fluoropyridin-4-yl) -6- (trifluoromethyl) thiazolo [5,4-b] pyridine (hereinafter referred to as present compound 9). The present compound 9 1 H-NMR (CDCI 3 ) δ: 8.96-8.94 (m, 1H), 8.76 (d, J = 2.4 Hz, 1H), 8.57 (dd, J = 5.1, 1.0 Hz, 1H), 8.65-8.64 (m, 1H), 8.32-8.28 (m, 1H) Production Example 9 2- (3-chloropyridin-4-yl) -6- (trifluoromethyl) thiazolo [5,4-b] pyridine (hereinafter referred to as the present compound 10) was obtained in the same way as in Production Example 8, with the exception of that 3 chloroisonicotinaldehyde was used instead of 3-fluoroisonicotinaldehyde. CL The present compound 10 1 H-NMR (CDCb) δ: 8.96-5.95 (m, 1H), 8.05 (s, 1H), 6.71 (d, J = 5.1 Hz, 1H) , 8.65-8.64 (m, 1H), 6.25 (d, J = 5.1 Hz, 1H) 86/100 Production Example 10 A mixture of 0.29 g of 2- (3-fluoropyridin-4-yl) -6- (trifluoromethyl) thiazolo [5,4-b] pyridine, 0.15 g of potassium carbonate and 6 ml of ethanol was refluxed with heating for 8 hours. The reaction mixture was cooled to room temperature. To the reaction mixture, water was added, and the resulting mixture was extracted twice with ethyl acetate. The combined organic layer was washed with saturated saline, dried over magnesium sulfate, then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 2- (3ethoxypyridin-4-yl) -6- (trifluoromethyl) thiazolo [5,4-b] pyridine (hereinafter, referred to as the present compound 11). The present compound 11 1 H-NMR (CDCIs) δ: 8.91-8.89 (m, 1H), 8.59-8.57 (m, 1H), 8.57 (s, 1H), 8, 46 (d, J = 4.9 Hz, 1H), 8.35 (d, J = 4.9 Hz, 1H), 4.47 (q, J = 7.0 Hz, 2H), 1.70 ( t, J = 7.0 Hz, 3H) Production Example 11 2- (3-methoxypyridin-4-yl) -5- (trifluoromethyl) thiazolo [5,4-h] pyridine (hereinafter referred to as the present compound 12) was obtained in the same way as in Production Example 10, except that methanol was used instead of ethanol. The present compound 12 1 H-NMR (CDCIs) δ: 8.91-8.90 (m, 1H), 8.61 (5, 1H), 8.60-8.58 (m, 1H), 8, 49 (d, J = 5.1 Hz, 1H), 8.35 (d, J = 5.0 Hz, 1H), 4.23 (s, 3H) Production Example 12 To a mixture of 51 mg of sodium hydride (60% dispersion 87/100 in mineral oil) and 2 ml of DMF a mixture of 0.10 g of 2,2-difluoro-ethanol and 1 ml of DMF was added at room temperature. This mixture was stirred at room temperature for 15 minutes, then cooled with ice. Then, to this was added a mixture of 0.29 g of 2- (3 fluoropyridin-4-yl) -6- (trifluoromethyl) thiazolo [5,4-h] pyridine and 10 ml of DMF, and the resulting mixture was stirred for 0.5 hour under cooling on ice, still for 0.5 hour at room temperature. To the reaction mixture, water was added, and the resulting mixture was extracted with ethyl acetate. The organic layer was washed with saturated saline, dried over magnesium sulfate, then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.27 g of 2- [3- (2,2difluoroethoxy) pyridin-4-yl] -6- (trifluoromethyl) thiazole [5,4-b] pyridine (hereinafter referred to as the present compound 13). The present compound 13 1 H-NMR (CDCI 3 ) δ: 8.94-8.92 (m, 1H), 8.62-8.60 (m, 1H), 8,588.56 (m, 2H), 8 , 40 (d, J = 5.1 Hz, 1H), 6.35 (tt, J = 54.6, 3.9 Hz, 1H), 4.59 (td, J = 12.7, 3.9 Hz, 2H) Production Example 13 A mixture of 0.20 g of 2- (3-fluoropyridin-4-yl) -6- (trifluoromethyl) thiazolo [5,4-b] pyridine, 47 mg of methylmercaptan sodium salt and 6 ml of DMF was stirred by 1 hour under ice cooling. To this mixture, 47 mg of methylmercaptan sodium salt were added, and the resulting mixture was stirred for another hour under ice cooling. To the reaction mixture, water was added, and the resulting mixture was extracted twice with ethyl acetate. The combined organic layers were washed with water and saturated saline, dried over magnesium sulfate, then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.19 g of 2- [3- (methylthio) pyridin-4-yl] -688/100 (trifluoromethyl) thiazolo [5,4-b] pyridine (hereinafter, referred to as the present compound 14). The present compound 14 1 H-NMR (CDCb) δ: 8.93-8.91 (m, 1H), 8.78 (s, 1H), 8.64-8.63 (m, 1H), 8.61 (d, J = 5.1 Hz, 1H), 7.91-7.89 (m, 1H), 2.62 (s, 3H) Production Example 14 A mixture of 0.90 g of 2- (3-fluoropyridin-4-yl) -6- (trifluoromethyl) thiazolo [5,4-b] pyridine, 0.32 g of ethylmercaptan sodium salt and 12 ml of DMF was stirred for 1 hour under ice cooling. To the reaction mixture, water was added, and the deposited solid was collected by filtration. This solid was washed with water, then dissolved in ethyl acetate. The organic layer was washed with saturated saline, dried over magnesium sulfate, then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.89 g of 2- [3- (ethylthio) pyridin15 4-yl] -6- (trifluoromethyl) thiazolo [5,4-b] pyridine (hereinafter , referred to as the present compound 15). The present compound 15 1 H-NMR (CDCb) δ: 8.93-8.92 (m, 1H), 8.85-8.84 (m, 1H), 8.64 (d, J = 5.1 Hz, 1H), 8.63-8.62 (m, 1H), 8.05-8.04 (m, 1H), 3.05 (q, J = 7.4 Hz, 2H), 1.36 (t, J = 7.4 Hz, 3H) Production Example 15 To a mixture of 0.62 g of 2- [3- (ethylthio) pyridin-4-yl] -6 (trifluoromethyl) thiazolo [5.4-b] pyridine and 5 ml of chloroform was added 0.66 g of 65 % m-chloroperbenzoic acid under cooling on ice. This mixture was stirred at 0 ° C for 1 hour. The reaction mixture was diluted with chloroform89 / 100 mio and washed sequentially with a 5% aqueous solution of sodium hydroxide and saturated saline. The organic layer was dried over magnesium sulfate, then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.27 g of 2- [35 (ethanesulfonyl) pyridin-4-yl] -6- (trifluoromethyl) thiazolo [5,4-b] pyridine (hereinafter , referred to as the present compound 16) and 0.28 g of 2- [3 (ethanesulfiniflpiridin-4-yl] -6- (trifluoromethyl) thiazolo [5,4-b] pyridine (hereinafter, referred to as the present compound 17) . The present compound 16 1 H-NMR (CDCI 3 ) δ: 9.41 (s, 1H), 9.07 (d, J = 4.9 Hz, 1H), 8,978.96 (m, 1H), 8, 58-8.55 (m, 1H), 7.65 (d, J = 5.0 Hz, 1H), 3.77 (q, J = 7.5 Hz, 2H), 1.43 (t, J = 7.4 Hz, 3H) The present compound 17 1 H-NMR (CDCI 3 ) δ: 9.49 (s, 1H), 8.98-8.96 (m, 2H), 8.59-8.57 (m, 1H), 7.82-7.80 (m, 1H), 3.51 (dq, J = 13.2, 7.5 Hz, 1H), 3.12 (dq, J = 13.2, 7, 4 Hz, 1H), 1.49 (t, J = 7.4 Hz, 3H) Production Example 16 To a mixture of 1.56 g of potassium ferricyanide and 4 ml of water, a mixture of 0.50 g of 3-chloro-N - [(420 trifluoromethyl) phenylthioisonicotinamide, 0.41 g of sodium hydroxide and 6 ml of water was poured at 60 ° C over a period of 45 minutes. After that, this mixture was stirred at 60 ° C for 2 hours. Then, 1.02 g of potassium carbonate was added, and the resulting mixture was stirred at 50 ° C for an additional 1 hour. The reaction mixture was cooled to room temperature, then 90/100 reaction mixture was extracted twice with diethyl ether. The combined organic layers were washed with saturated saline, dried over magnesium sulfate, then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 60 mg of 2- (3-chloropyridin-4-yl) -6- (trifluoromethyl) benzothiazole (hereinafter, referred to as the present compound 18). The present compound 18 1 H-NMR (CDCfe) δ: 8.81 (s, 1H), 8.67 (d, J = 5.1 Hz, 1H), 8.308.28 (m, 2H), 8.28 -8.24 (m, 1H), 7.82-7.79 (m, 1H) Production Example 17 To a mixture of 2.77 g of potassium ferricyanide and 20 ml of water, a mixture of 0.70 g of 3-chloro-N - [(4-trifluoromethoxy) phenyl] thioisonicotinamide, 0.67 g of sodium hydroxide , 5.6 ml of water and 8 ml of ethanol was poured at 90 ° C in a period of 20 minutes. After that, this mixture was stirred at 90 ° C for 1 hour. The reaction mixture was cooled to room temperature. The reaction mixture was extracted twice with diethyl ether. The combined organic layers were washed with saturated saline, dried over magnesium sulfate, then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.18 g of 2- (3-chloropyridin-4-yl) -6- (trifluoromethoxy) benzothiazole (hereinafter referred to as the present compound 19). F 3 CO ' The present compound 19 1 H-NMR (CDCI 3 ) δ: 8.81 (s, 1H), 8.67-8.65 (m, 1H), 8.26 (d, J = 5.1 Hz, 1H ), 8.18 (d, J = 8.8 Hz, 1H), 7.87-7.86 (m, 1H), 7.47-7.43 (m, 1H) Next, Reference Production Examples are shown for the production of production intermediates for the inventive compounds described above. Reference Production Examples 1 To a mixture of 9.84 g of 2-hydroxy-5- (trifluoromethyl) pyridine and 40 ml of concentrated sulfuric acid, 10.9 g of 70% nitric acid were poured at 80 ° C. This mixture was stirred at 80 ° C for 1 hour. The reaction mixture was cooled to room temperature, then the reaction mixture was poured into ice water. The deposited solid was collected by filtration. This solid was washed with ice water, then dissolved in ethyl acetate, and washed with saturated saline. The organic layer was dried over magnesium sulfate, then concentrated under reduced pressure, to obtain 5.22 g of 2-hydroxy-5-nitro-5- (trifluoromethyl) pyridine. 1 H-NMR (DMSO-d 6 ) δ: 13.54 (br s, 1H), 8.67 (d, J = 2.7 Hz, 1H), 8.48- 8.45 (m, 1H) A mixture of 5.22 g of 2-hydroxy-3-nitro-5 (trifluoromethyl) pyridine, 4.2 g of phosphorus oxychloride and 2.0 g of quinoline was refluxed with heating for 5.5 hours. The reaction mixture was cooled to room temperature, then the reaction mixture was poured into ice water. This mixture was neutralized with an aqueous solution of sodium hydroxide, then the mixture was extracted twice with ethyl acetate. The combined organic layers were washed with water and saturated saline, dried over magnesium sulfate, then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 4.88 g of 2-chloro-3-nitro-5- (trifluoromethyl) pyridine. 1 H-NMR (CDCI 3 ) δ: 8.91-8.87 (m, 1H), 8.48-8.44 (m, 1H) A mixture of 4.88 g of 2-chloro-3-nitro-5- (trifluoromethyl) pyridine, 1.81 g of thiourea and 40 ml of ethanol was stirred at 50 ° C for 5.5 hours. The reaction mixture was cooled to room temperature, then concentrated under reduced pressure. To the residue were added 24 ml of water and a mixture of 2.8 g of sodium hydroxide and 6 ml of water, which was stirred at room temperature for 1.5 hours. The reaction mixture was washed with diethyl ether, then acetic acid was added. This was cooled with ice, and the deposited solid was collected by filtration. This solid was dried under reduced pressure, to obtain 3.84 g of 3-nitro-5- (trifluoromethyl) pyridine-2-thiol. F 3 C 1 H-NMR (DMSO-de) δ: 8.53 (d, J = 2.2 Hz, 1H), 8.38-8.36 (m, 1H) To a mixture of 2.87 g of iron, 10 ml of acetic acid and 10 ml of water were added a mixture of 3.84 g of 3-nitro-5 (trifluoromethyl) pyridine-2-thiol and 10 ml of ethyl acetate at 70 ° C over a period of 10 minutes . The reaction mixture was cooled to room temperature, then, to the reaction mixture, water was added, and the resulting mixture was extracted twice with ethyl acetate. The combined organic layers were washed with water and saturated saline, dried over magnesium sulfate, then concentrated under reduced pressure to obtain 3.1 g of 3-amino-5- (trifluoromethyl) pyridine-2-thiol. 1 H-NMR (DMSO-de) δ: 13.85 (br s, 1H), 7.43-7.40 (m, 1H), 6.836.82 (m, 1H), 6.16 (brs, 2H ) Reference Production Example 2 A mixture of 1.53 g of 4-trifluoromethylaniline, 1.50 g of 3-chloroisonicotic acid, 2.37 g of 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride (hereinafter referred to as WSC) and 10 ml of pyridine was stirred at 60 ° C for 1 hour. The reaction mixture was cooled to room temperature. To the reaction mixture, water was poured, and the resulting mixture was extracted twice with ethyl acetate. The combined organic layers were washed with water and saturated saline, dried over magnesium sulfate25 93/100 then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 1.59 g of 3-chloro-N - [(4trifluoromethyl) phenyl] isonicotinamide. 1 H-NMR (CDCb) δ: 8.73 (s, 1H), 8.66 (d, J = 4.9 Hz, 1H), 8.20 (br s, 1H), 7.78 (d, J = 8.3 Hz, 2H), 7.70-7.64 (m, 3H) A mixture of 1.59 g of 3-chloro-N - [(4-trifluoromethyl) phenylisonicotinamide, 1.07 g of 2,4-bis (4-methoxyphenyl) -1,3-dithia-2,4-diphosphethane- 2,4 disulfide (hereinafter referred to as Lawesson's reagent) and 7 ml of toluene was refluxed with heating for 3.5 hours. The reaction mixture was cooled to room temperature, then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 1.47 g of 3-chloro-N-1 (4-trifluoromethyl) phenylthioisonicotinamide. 1 H-NMR (CDCb) δ: 9.41 (br s, 1H), 8.60 (s, 1H), 8.54 (d, J = 5.0 Hz, 1H), 8.03 (d, Hz, 2H), 7.73 (d, J = 8.6 Hz, 2H), 7.51 (d, J = 5.0 Hz, 1H) Reference Production Example 3 A mixture of 1.69 g of 4-trifluoromethoxyaniline, 1.50 g of 3-chloroisonicotic acid, 2.37 g of WSC and 10 ml of pyridine was stirred at 60 ° C for 1.3 hours. The reaction mixture was cooled to room temperature. The reaction mixture was poured into water. This mixture was extracted twice with ethyl acetate. The combined organic layers were washed with water and saturated saline, dried over magnesium sulfate, then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 2.87 g of 3-chloro-N - [(4trifluoromethoxy) phenyl] isonicotinamide. 94/100 1 H-NMR (CDCI 3 ) δ: 8.71 (s, 1H), 8.63 (d, J = 5.1 Hz, 1H), 8.14 (br s, 1H), 7.68 (d , J = 8.8 Hz, 2H), 7.65 (d, J = 5.1 Hz, 1H), 7.26 (d, J = 8.8 Hz, 2H) A mixture of 0.62 g of 3-chloro-N - [(4-trifluoromethoxy) phenyl] isonicotinamide, 0.40 g of Lawesson's reagent and 5 ml of toluene was refluxed with heating for 4 hours. The reaction mixture was cooled to room temperature, then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.56 g of 3 chloro-N - [(4-trifluoromethoxy) phenyl] thioisonicotinamide. 1 H-NMR (CDCIs) δ: 8.94 (br s, 1H), 8.67 (s, 1H), 8.58 (d, J = 5.0 Hz, 1H), 7.89 (d, J = 8.9 Hz, 2H), 7.53 (d, J = 5.1 Hz, 2H), 7.33 (d, J = 8.9 Hz, 1H) Next, Formulation Examples of the present compound are shown. The parts are by weight. Formulation Example 1 Ten (10) parts of any of the compounds present (1) to (19) described above were dissolved in a mixture of 35 parts of xylene and 35 parts of Ν, Ν-dimethylformamide, and 14 parts of polyoxyethylene styrene phenyl ester and 6 parts of calcium dodecylbenzenesulfonate were added, and mixed to obtain an emulsifiable concentrate. Formulation Example 2 Four (4) parts of sodium lauryl sulfate, 2 parts of calcium ligninsulfonate, 20 parts of a fine powder of synthetic hydric silicon oxide and 54 parts of diatomaceous earth were mixed, and 20 parts of any of the compounds present (1) to (19) described above were added, and mixed to obtain an swelling powder. 95/100 Formulation Example 3 To 2 parts of any of the compounds present (1) to (19) described above was added 1 part of a fine powder of synthetic hydrous silicon oxide, 2 parts of calcium ligninsulfonate, 30 parts of bentonite and 65 parts of clay kaolin, and mixed. Then, to this mixture an adequate amount of water was added, the mixture was further stirred, granulated by a granulator, and dried under ventilation to obtain a granule. Formulation Example 4 A part of any of the compounds present (1) to (19) described above was dissolved in an appropriate amount of acetone, and to this was added 5 parts of a fine powder of synthetic hydrous silicon oxide, 0.3 part of PAP and 93.7 parts of Eubasami clay, and sufficiently agitated to mix, and acetone was removed by distillation to obtain a powder. Formulation Example 5 Thirty five (35) parts of a mixture (weight ratio 1: 1) of ammonium salt of polyoxyethylene alkyl ether sulfate and white carbon, 10 parts of any of the compounds present (1) to (19) described above and 55 parts of water were mixed, and finely sprayed by a wet spray method to obtain a formulation. Formulation Example 6 Zero point one (0.1) part of any of the compounds present (1) to (19) described above was dissolved in 5 parts of xylene and 5 parts of trichloroethane, and this solution was mixed with 39.9 parts of deodorized kerosene , to obtain an oil solution. Formulation Example 7 Ten (10) mg of any of the compounds present (1) to (19) described above were dissolved in 0.5 ml of acetone, and 5 g of this solution was used to treat a solid animal powder (substance powder) solid breeding propagation CE-2, manufactured by CLEA Japan Inc.), and mixed uniformly. Then, acetone was evaporated to dryness, to obtain a poisonous bait. 96/100 Formulation Example 8 zero point one (0.1) part of any of the compounds present (1) to (19) described above and 49.9 parts of Neotiozol (Chue Kasei Co. Ltd.) were loaded into an aerosol pot which was then equipped with an aerosol valve, then 25 parts of dimethyl ether and 25 parts of LPG were filled and vibration was applied, and an actuator was mounted to obtain an aerosol of the oil solution. Formulation Example 9 Zero point six (0.6) part of any of the compounds present (1) to (19) described above, 0.01 part of BHT (2,6-di-tert-butyl-4methylphenol), 5 parts of xylene, 3.39 parts of deodorized kerosene and 1 part of an emulsifier (Atmos 300 (trade name for Atmos Chemical)) were mixed and dissolved, and the resulting solution and 50 parts of distilled water were filled into an aerosol vessel which was then equipped with a valve, then 40 parts of an injection agent (LPG) was filled under pressure through the valve, to obtain an aqueous aerosol. Then, the arthropod plague control effect of the present compound is shown through the test examples. Test Example 1 The compounds present (1), (2), (4) to (12), (14) to (17) and (19) were formulated by the method in Formulation Example 5. This formulation was diluted with water so that the active ingredient concentration was 500 ppm, to prepare a diluted test solution. A cucumber seedling (first stage of true leaf propagation) planted in a plastic cup was inoculated with about 30 Aphis gossypii, and left for 1 day. On this cucumber seedling, the diluted solution described above for testing (20 ml) was sprayed. Six days after spraying, the number of live parasitic Aphis gossypii insects on the leaves of the cucumber was verified, and the control value was calculated according to the following formula. Control value (%) = [1- (Cb x Tai) / (Cai x Tb) j x 100 The letters in the formula represent the following meanings. 97/100 Cb: number of insects before treatment in untreated area Cai: number of insects under observation in untreated area Tb: number of insects before treatment in the treated area Tai: number of insects under observation in treated area As a result, the treated areas treated by the compounds present (1), (2), (4) to (12), (14) to (17) and (19) showed a control value of 90% or more. Test Example 2 The compounds present (7), (9), (12), (14), (16) and (17) were formulated by the method in Formulation Example 5. This formulation was diluted with water so that the concentration of active ingredient was 500 ppm, to prepare a diluted solution for testing. This diluted test solution (5 ml) was placed in a plastic cup. A soil around a cucumber seedling (first stage of true leaf propagation) was removed, and part of the root of this seedling was washed with water. The root part of this seedling was immersed in the diluted test solution placed in the plastic cup described above. One day later, the surface of the cucumber leaf was inoculated with 30 Aphis gossypii (whole stage). Another 7 days later, the number of live parasitic Aphis gossypii insects on the leaves of this cucumber was verified. The control value was calculated according to the following formula. Control value (%) = [1 - (Cb x Tai) / (Cai x Tb)] x 100 The letters in the formula represent the following meanings. Cb: number of insects before treatment in untreated area Cai: number of insects under observation in untreated area Tb: number of insects before treatment in the treated area Tai: number of insects under observation in treated area As a result, the treated areas treated by the present compounds (7), (9), (12), (14), (16) and (17) showed a control value of 90% or more. Test Example 3 98/100 The present compound (7) was formulated by the method in Formulation Example 5. This formulation was diluted with water so that the concentration of active ingredient was 200 ppm to prepare a diluted test solution. The diluted test solution (5 ml) was used to treat a cucumber seedling (first stage of true leaf propagation) planted in a plastic cup. This cucumber was left in a greenhouse at 25 ° C for 7 days. Then, the surface of the cucumber leaf was inoculated with 30 Aphis gossypii (whole stage). This cucumber was still left in the greenhouse for 6 days, then the number of live parasitic Aphis gossypii insects on the leaves of this cucumber was verified, and the control value was calculated according to the following formula. Control value (%) = [1- (Cb x Tai) / (Cai x Tb)] x 100 The letters in the formula represent the following meanings. Cb: number of insects before treatment in untreated area Cai: number of insects under observation in untreated area Tb: number of insects before treatment in the treated area Tai: number of insects under observation in treated area As a result, the treated area treated by the diluted test solution for the present compound (7) showed a control value of 90% or more. Test Example 4 The compounds present (1), (4) to (7), (9) to (12) and (14) to (19) were formulated by the method in Formulation Example 5. This formulation was diluted with water so that the active ingredient concentration was 200 ppm, to prepare a diluted test solution. In a tomato seedling planted in a plastic cup, adult insects of Bemisia tabaci were released and allowed to lay eggs for about 24 hours. The tomato seedling was left in a greenhouse for 8 days. After that, the diluted test solution was sprayed at a rate of 10 ml / cup. In addition, this tomato seedling was placed in an oven at 25 ° C for 7 days. After that, the number of larvae that remain in the 99/100 tomato leaves were checked, and the control value was calculated according to the following formula. Control value (%) = [1- (Cb x Tai) / (Cai x Tb)] x 100 The letters in the formula represent the following meanings. Cb: number of insects before treatment in untreated area Cai: number of insects under observation in untreated area Tb: number of insects before treatment in treated area Tai: number of insects under observation in treated area As a result, the treated areas treated by the compounds present (1), (4) a (7), (9) to (12) and (14) to (19) showed a control value of 90% or more. Test Example 5 The compounds present (1) to (7), (9) to (15) and (17) to (19) were formulated by the method in Formulation Example 5. This formulation was .15 diluted with water so that the concentration of active ingredient was 500 ppm, to prepare a diluted solution for testing. In a rice seedling (2 weeks after sowing, second leaf propagation stage) planted in a plastic cup, the diluted test solution (10 ml) was sprayed. The sprayed drug solution to treat the rice seedling was dried, then 20 larvae of the first instar of Nilaparvata lugens were released. This rice seedling was placed in a greenhouse at 25 ° C for 6 days. After that, the number of Nilaparvata parasitic lugens in the rice was verified, and the control value was calculated according to the following formula. Control value (%) = [1- (Cb x Tai) / (Cai x Tb)] x 100 The letters in the formula represent the following meanings. Cb: number of insects before treatment in untreated area Cai: number of insects under observation in untreated area Tb: number of insects before treatment in treated area Tai: number of insects under observation in treated area As a result, the treated areas treated by the compounds present (1) to (7), (9) to (15) and (17) to (19) showed a control value 100/100 of 90% or more. INDUSTRIAL APPLICABILITY The present compound is useful for the control of arthropod pests 1/4
权利要求:
Claims (8) [1] 1. Heterocyclic compound represented by formula (1): n 0) t on what A 1 and A 2 are the same or different and represent a nitrogen atom or = C (R 5 ) -, R 1 represents a C1-C6 chain hydrocarbon group optionally substituted by at least one member selected from Group X, a C3-C6 alicyclic hydrocarbon group optionally substituted by at least one member selected from Group X, phenyl group optionally substituted by at least one member selected from Group Y, 5-membered heterocyclic group optionally substituted by at least one member selected from Group Y, 6-membered heterocyclic group optionally replaced by at least one member selected from Group Y, -OR 5 , -S (O) mR 6 , -NR 6 R 7 , -NR 6 C (O) R 8 , -NR 6 CO 2 R 9 , -C (O) R 10 , -C (NOR 6 ) R 10 , cyano group, nitro group or atom halogen, R 2 represents a C 1 -C 6 chain hydrocarbon group optionally substituted by at least one member selected from Group X, -OR 6 , -S (O) mR 6 , -NR 6 R 7 , halogen atom or hydrogen atom, R 3 and R 4 are the same or different and represent a C1-C4 chain hydrocarbon group substituted by at least one halogen atom, -OR 11 , -S (O) mR 11 , halogen atom or hydrogen atom (with the condition that R 3 or R 4 represents a C1-C4 chain hydrocarbon group substituted by at least one halogen atom, -OR 11 or S (O) mR 11 ), alternatively, R 3 and R 4 can be linked to form a 5-membered ring or 6-membered ring replaced by one or more halogen atoms along with the carbon atoms to which R 3 and R 4 are attached, R 5 represents a C1-C3 alkyl group optionally substituted by at least one halogen atom, halogen atom or [2] 2/4 hydrogen, R 6 and R 7 are the same or different and represent a C1-C6 chain hydrocarbon group optionally substituted by at least one member selected from Group X, group C4-C7 cycloalkylmethyl optionally substituted by at least one member selected from Group X, group C3-C6 alicyclic hydrocarbon optionally substituted by at least one member selected from Group X, phenyl group optionally substituted by at least one member selected from Group Y, benzyl group optionally substituted by at least one member selected from Group Y, 5 membered heterocyclic group optionally substituted by at least one member selected from Group Y, a 6-membered heterocyclic group optionally substituted by at least one member selected from Group Y, or hydrogen atom (with the proviso that R 6 does not represent a hydrogen atom when m in -S (O) m R 6 is 1 or 2), R 8 represents a hydrocarbon group of Ci-C6 chain optionally substituted by at least one member selected from Group X, alicyclic hydrocarbon group , C 3 -C 6 -cycloalkyl optionally substituted by at least one member selected from Group X, or feniia group optionally substituted by at least one selected member of Group Y, R 9 represents a C1-C4 alkyl group optionally substituted by at least one halogen atom, R 10 represents a CI-C4 alkyl group optionally substituted by at least one halogen atom, or hydrogen atom, R 11 represents a CÚ-C4 chain hydrocarbon group substituted by at least one halogen atom, m represents 0, 1 or 2, and n represents 0 or 1; Group X: the group consisting of C1-C4 alkoxy groups optionally substituted by at least one halogen atom, and halogen atoms; Group Y: the group consisting of CÕ-C4 alkyl groups optionally substituted by at least one halogen atom, C1-C4 alkoxy groups optionally substituted by at least one halogen atom, cyano group, [3] 3/4 nitro group and halogen atoms. Heterocyclic compound according to claim 1, wherein R 5 is a hydrogen atom. Heterocyclic compound according to claim 1, wherein R 2 is a hydrogen atom. [4] Heterocyclic compound according to claim 1, wherein R 1 is a C 1 -C 6 chain hydrocarbon group optionally substituted by at least one member selected from Group X, -OR 6 , S (O) mR 6 , -NR 6 R 7 , -NR 6 C (O) R 8 , -NR 6 CO 2 R 9 , -C (O) R 10 , -C (NOR 6 ) R 10 , cyano group, nitro group or halogen atom, R 6 and R 7 are the same or different and are a C ^ Cg chain hydrocarbon group optionally substituted by at least one member selected from Group X, or hydrogen atom (with the proviso that R 6 is a chain hydrocarbon group) C ^ Ce optionally substituted by at least one member selected from Group X when m in -S (O) m R 6 is 1 or 2), and R 8 is a C ^ Cg chain hydrocarbon group optionally substituted by at least one member selected from Group X. [5] Heterocyclic compound according to claim 4, wherein R 1 is a C 1 -C 6 chain hydrocarbon group optionally substituted by at least one member selected from Group X, -OR 6 , -S (O) mR 6 , -NR 6 R 7 or halogen atom, R 6 is a Ci-C 6 chain hydrocarbon group optionally substituted by at least one member selected from Group X, and R 7 is a CiC 6 chain hydrocarbon group optionally substituted by at least one member selected from Group X, or hydrogen atom. [6] 6. Arthropod plague control composition comprising the 4/4 heterocyclic compound as defined in claim 1, and an inert vehicle. [7] 7. Arthropod plague control method comprising applying an effective amount of the heterocyclic compound as defined in claim 1 to arthropod pests or areas where arthropod pests live. [8] 8. Use of the heterocyclic compound as defined in claim 1 for the control of arthropod pests. 1/1
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公开号 | 公开日 TWI457343B|2014-10-21| EP2486035B1|2015-08-26| US20120196891A1|2012-08-02| AR078520A1|2011-11-16| WO2011043404A1|2011-04-14| US8742112B2|2014-06-03| EP2486035A4|2013-02-27| JP2011079774A|2011-04-21| CN102686585A|2012-09-19| TW201116539A|2011-05-16| JP5540640B2|2014-07-02| EP2486035A1|2012-08-15| BR112012007844A2|2015-09-22| CN102686585B|2014-10-08|
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法律状态:
2016-05-31| B06F| Objections, documents and/or translations needed after an examination request according [chapter 6.6 patent gazette]| 2017-04-18| B07D| Technical examination (opinion) related to article 229 of industrial property law [chapter 7.4 patent gazette]| 2017-10-31| B07G| Grant request does not fulfill article 229-c lpi (prior consent of anvisa) [chapter 7.7 patent gazette]| 2018-02-06| B15K| Others concerning applications: alteration of classification|Ipc: C07D 417/04 (2006.01), C07D 513/04 (2006.01), A01N | 2018-02-14| B09A| Decision: intention to grant [chapter 9.1 patent gazette]| 2018-03-13| B16A| Patent or certificate of addition of invention granted [chapter 16.1 patent gazette]|
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申请号 | 申请日 | 专利标题 JP2009-233158|2009-10-07| JP2009233158A|JP5540640B2|2009-10-07|2009-10-07|Heterocyclic compounds and their use for controlling harmful arthropods| PCT/JP2010/067609|WO2011043404A1|2009-10-07|2010-09-30|Heterocyclic compound and its use for control of an arthropod pest| 相关专利
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