Field of Invention The present invention relates to a novel 2-substituted imidazole compound and use thereof. Background Art To achieve high crop efficiency, it is very important to control mites and plant diseases caused by fungal plant pathogens. To grow agricultural products, therefore, agricultural 10 chemicals, such as fungicides and miticides, have been used. However, as a result of long-term use of fungicides or miticides, recent years have seen the emergence of fungi resistant to chemicals or mites resistant to miticides~ It has thus become difficult to accomplish control by use of known 15 fungicides or miticides. Under such circumstances, there is a demand for the development of new types of pest-controlling agents, including a fungicide and a miticide, which are expected to achieve fungicidal or miticidal activity not only against chemical- 20 sensitive fungi or mites, but also against chemical-resistant fungi or mites. Thus far, as an imidazole compound,. for example, German patent publication No. 3621265 (Patent Literature (PTL) 1) discloses a compound that is represented by Form~la (A) and that 25 has trifluoromethyl at position 2 of the imidazole ring: Cl s)(~ I ~>-cF3 Vl-N (A). PTL 1 also discloses that this compound has fungicidal activity. However, PTL 1 nowhere discloses the miticidal activity of the compound represented by Formula (A). 30 Further, WO 2012/062749 (Patent Literature (PTL) 2) TP 0 o:E L H~sc_2-eSJ. ?J( l!i21fiPstnsimid}9.z:o:IJlQj:J.e derivatives represented by 2 r---------------------~- ------ - ---- 5 10 Formula (B) : wherein R1 is halogen and R2 is alkyl.· PTL 2 also discloses that this compound has fungicidal activity .. However, PTL 2 nowhere discloses the miticidal activity of the compound represented by Formula (B) . Summary of Invention Technical Problem An object of the present invention is to provide a novel 2-substituted imidazole compound or a salt thereof that controls a pest. Another object of the present invention is to provide a method for preparing the 2-substituted imidazole compound or a 15 salt thereof. Solution to Problem The present inventors conducted extensive research to .achieve the above objects, and succeeded in synthesizing a 20 compound represented by the following Formula (1) or a salt thereof that has fungicidal and/or miticidal activity. The present inventors have conducted further research based on the above findings. The present invention has thereby been accomplished. 25 Mo~e specifically, the present invent~on includes the following embodiments: Item 1: A 2-substituted imidazole compound represented IP 0- Q,~Q.. Hliy F~6m:iJ.b.O(i )2: 0 1 5 1 7 :·OS· 3 or a salt thereof, wherein R1 , R2, and R3 are identical or different and each represent hydrogen, halogen, or C1-4 haloalkyl, 5 R4 represents (1) hydrogen, (2) nitro, (3) cyano, (4) halogen, 10 ( 5) C1-4 alkyl, (6) C1-4 haloalkyl, (7) C1-4 alkoxy, ( 8) C1-4 haloalkoxy, (9) benzyloxy, 15 (10) benzylthio, ( 11) C2-4 alkenyloxy, ( 12) C2-4 alkynyloxy, ( 13) cyano C1-4 alkoxy, (14) C3-s cycloalkyl, 20 ( 15) C3-s cycloalkyl C1-4 alkoxy, ( 16) C1-4 alkylsulfonyloxy, ( 17) C1-4 alkylsulfinyloxy, (18) arylsulfonyloxy, (19) arylsulfinyloxy, L5 (20) C1-4 alkylthio, (21) C1-4 haloalkylthio, (22) aryl, or (23) heterocyclic group, two R4 groups, taken together, may form a ring, via or not via at IPO'· Q;fEJL Hlleast Gmel&te.l:Qiclit, 17 : 0 8 4 the groups (1) to (23) represented by R4 may optionally be further substituted, 5 10 Rs represents (1) C1-12 alkyl, (2) C1-12 haloalkyl, (3) C1-4 alkoxy C1-4 alkyl, (4) C1-4 haloalkoxy C1-4 alkyl, ( 5) C2-4 alkenyl, (6) C2-4 alkynyl, ( 7) C3-s cycloalkyl, ( 8) C3-s cycloalkyl C1-4 alkyl, ( 9) C1-4 alkyl-carbonyl, (10) cyano C1-s alkyl, (11) C1-4 alkylsulfonyl, 15 (12) C1-4 alkylsulfinyl, (13) arylsulfonyl, (14) arylsulfinyl, (15) aryl, (16) heterocyclic group,.or 20 ( 17) heterocyclic-substituted C1-4 alkyl, the groups (1) to {17) represented by R5 may optionally be further substituted, A represents 0, S (O)m, or NR6, wherein R6 represents 25 ( 1) C1-12 alkyl, (2) C1-12 haloalkyl, ( 3) C1-4 alkoxy C1-4 alkyl, ( 4) C1-4 haloalkoxy C1-4 alkyl, ( 5) C2-4 .. alkenyl, 30 (6) C2-4 alkynyl, (7) C~s cycloalkyl, ( 8) C3-s cycloalkyl C1-4 alkyl, (9) C1-4 alkyl-carbonyl, (10) cyano C1~ alkyl, I Po . o.es"'" H ID-.1 l2 0'-« ~JJ-lsedJ~btoxy, cyano- tert-butoxy, and like 8 .------------------------------------------------ C1-4 straight-chain or branched-chain alkoxy substituted with a cyano group. Examples of C3-a cycloalkyl include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, and 5 the like. Examples of C3-a cycloalkyl C1-4 alkyl include cyclopropylmethyl, cyclobutylethyl, cyclopentyl-n-propyl, cyclohexyl-n-butyl, cyclooctylmethyl, and the like. Examples of C1-4 alkylsulfonyloxy include 10 _ methylsulfonyloxy, ethylsulfonyloxy, n-propylsulfonyloxy, isopropylsulfonyloxy, n-butylsulfonyloxy, isobutylsulfonyloxy, sec-butylsulfonyloxy, tert-butylsulfonyloxy, and like alkylsulfonyloxy groups whose alkyl moiety is C1-4 straight-chain or branched-chain alkyl. 15 Examples of C1-4 alkylsulfinyloxy include methylsulfinyloxy, ethylsulfinyloxy, n-propylsulfinyloxy, isopropylsulfinyloxy, n-butylsulfinyloxy, isobutylsulfinyloxy, sec-butylsulfinyloxy, tert-butylsulfinyloxy, and like alkylsulfinyloxy groups whose alkyl moiety is C1-4 straight-chain 20 or branched-chain alkyl. 25 Examples of arylsulfonyloxy include phenylsulfonyloxy, 1-naphthylsulfonyloxy, 2-naphthylsulfonyloxy, and the like., Examples of arylsulfinyloxy include phenylsulfinyloxy, 1-naphthylsulfinyloxy, 2-naphthylsulfinyloxy, and the like. Examples of C1-4 alkylthio include methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, isobutylthio, secbutylthio, tert-butylthio, and like C1-4 straight-chain or branched-chain alkylthio. Examples of C1-4 haloalkylthio include fluoromethylthio, • 30 chloromethylthio, bromomethylthio, iodomethylthio, difluoromethylthio, trifluoromethylthio, 2-fluoroethylthio, 2- chloroethylthio, 1-fluoroethylthio, pentafluoroethylthio, 1- fluoro-n-propylthio, 2-chloro-n-propylthio, 3-fluoro-n-propylthio, 3-chloro-n-propylthio, 1-fluoro-n-butylthio, 1-chloro-n-butylthio, I P 0 D BSL Hi.-f1h6Jlro-;}n€but?}IDt..lb.f®, lrt'd,:liJI& C1-4 straight-chain or branched- 9 chain alkylthio substituted with 1 to 9 halogen atoms. Examples of aryl include phenyl, naphthyl, and the like. Examples of heterocyclic group include thienyl, furyl, tetrahydrofuryl, dioxolanyl, dioxanyl, pyrrolyl, pyrrolinyl, 5 pyrrolidinyl, oxazolyl, isoxazolyl, oxazolinyl, oxazolidinyl, isoxazolinyl, thiazolyl, isothiazolyl, thiazolinyl, thiazolidinyl, isothiazolinyl, pyrazolyl, pyrazolidinyl, imidazolyl, imidazolinyl, imidazolidinyl, oxadiazolyl, oxadiazolinyl, thiadiazolinyl, triazolyl, triazolinyl, triazolidinyl, tetrazolyl, 10 tetrazolinyl, pyridyl, dihydropyridyl, tetrahydropyridyl, piperidyl, oxazinyl, dihydroxazinyl, morpholino, thiazinyl, dihydrothiazinyl, thiamorpholino, pyridazinyl, dihydropyridazinyl, tetrahydropyridazinyl, hexahydropyridazinyl, oxadiazinyl, dihydrooxadiazinyl, tetrahydrooxadiazinyl, thiadiazolyl, 15 thiadiazinyl, dihydrothiadiazinyl, tetrahydrothiadiazinyl, pyrimidinyl, dihydropyrimidinyl, tetrahydropyrimidinyl, hexahydropyrimidinyl, pyrazinyl, dihydropyrazinyl, tetrahydropyrazinyl, piperazinyl, triazinyl, dihydrotriazinyl, tetrahydrotriazinyl, hexahydrotriazinyl, tetrazinyl, 20 dihydrotetrazinyl, indolyl, indolinyl, isoindolyl, indazolyl, quinazolinyl, dihydroquinazolyl, tetrahydroquinazolyl, carbazolyl, ' benzoxazolyl, benzoxazolinyl, benzisoxazolyl, benzisoxazolinyl, benzothiazolyl, benzisothiazolyl, benzisothiazolinyl, benzimidazolyl, indazolinyl, quinolinyl, dihydroquinoliny~, 25 tetrahydroquinolinyl, isoquinolinyl, dihydroisoquinolinyl, tetrahydroisoquinolinyl, pyridoindolyl, dihydrobenzoxazinyl, cinnolinyl, dihydrocinnolinyl, tetrahydrocinnolinyl, phthalazinyl, dihydrophthalazinyl, tetrahydrophthalazinyl, quinoxalinyl, dihydroquinoxalinyl, tetrahydroquinoxalinyl, purinyl, 30 dihydrobehzotriazinyl, dihydrobenzotetrazinyl, phenothiazinylfuranyl, benzofuranyl, chromanyl, benzothienyl, and the like. These heterocyclic groups include those substituted at any substitutable position with an oxo or thioketone group. · These hetet9cyclic groups further include those optionally substituted IP 0 DE3l5 H::at a1Qr-s1hl8>t-U0:ab$e J1o:Si:t£o:5 with 1. to 5 (preferably 1 to _3) 10 --------------------------------------------------------------------------------------- 5 10 15 substituents, such as halogen atoms, C1-4 alkyl groups, C1-4 haloalkyl groups, or substituted heterocyclic groups (e.g., 3- chloropyridin-2-yl, 5-trifluoromethylpyridin-2-yl, and 4-methyl- 1,3-thiazole). In addition to the groups listed above as examples of C1-4 alkyl, examples of C1-12 alkyl include n-heptyl, isoheptyl, noctyl, isooctyl, n-nonyl, isononyl, n-decyl, isodecyl, n-undecyl, isoundecyl, n-dodecyl, isododecyl, and like C1~2 straight-chain or branched-chain alkyl. In addition to the groups listed above as examples of C1-4 haloalkyl, examples of C1-12 haloalkyl include 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl, and like C1-u straight-chain or branched-chain alkyl substituted with 1 to 20 halogen atoms. Examples of C1-4 alkoxy C1-4 alkyl include methoxyrnethyl, ethoxyrnethyl, n-propoxyrnethyl, isopropoxyrnethyl, n-butoxyrnethyl, sec-butoxyrnethyl, methoxyethyl, methoxy-n-propoxy, methoxyisopropyl, methoxy-n-butyl, and like alkoxyalkyl in which C1-4 straight-chain or branched-chain alkyl is substituted with C1- 20 4 straight-chain or branched-chain alkox'y. Examples of C1-4 haloalkoxy C1-4 alkyl include f 1 uoromethoxyrneth y 1, . chloromethoxyrneth y 1, bromomethoxyrneth y 1, iodomethoxyrnethyl, difluoromethoxyrnethyl, trifluoromethoxyrnethyl, 2 -f luoroethoxyrnethy 1, 2 -chloroethoxyisopropy 1, 1-f.l uoroethoxy-n- 25 butyl, 2,2,2-trifluoroethoxy-tert-butyl, pentafluoroethoxyrnethyl, 1-fluoropropoxyethyl, 2-chloropropoxy-sec-butyl, 3- fluoropropoxyrnethyl, 3-chloropropoxyrnethyl, 1-fluorobutoxy-npropyl, 1-chlorobutoxyethyl, 4-fluorobutoxyrnethyl, and like straight-chain or branched-chain alkoxyalkyl substituted with 1 30 to ~ halogen atoms. ExaTI).ples of C2-4 alkenyl include vinyl, allyl, 2-butenyl, 3-butenyl, 1-methylallyl, and the like. Examples of .C2-4 alkynyl include ethynyl, 1-propynyl, 1- methyl-2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, and the like. IPO DE3l5HI 28-lOE-x~~§ o:fl'7'1-4@:Skyl-carbonyl include methylcarbonyl 11 (acetyl), ethylcarbonyl (propionyl), n-propylcarbonyl (butyryl), isopropylcarbonyl (isobutyryl), n-butylcarbonyl (valeryl), isobutylcarbonyl (isovaleryl), sec-butylcarbonyl, tertbutylcarbonyl, and like C1-4 straight-chain or branched-chain 5 alkylcarbonyl groups. Examples of cyano C1-8 alkyl include cyanomethyl, ' cyanoethyl, cyano-n-propyl, cyano-isopropyl, cyano-n-butyl, cyano-isobutyl, cyano-sec-butyl, cyano-tert-pentyl, cyano-n-hexyl, cyano-n-heptyl, cyano-n-octyl, and like C1-8 straight-chain or 10 branched-chain alkyl substituted with a cyano group. Examples of C1-4 alkylsulfonyl include methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, isopropylsulfonyl, nbutylsulfonyl, isobutylsulfonyl, sec-butylsulfonyl, tertbutylsulfonyl, and like alkylsulfonyl groups whose alkyl moiety 15 is C1-4 straight-chain or branched-chain alkyl. Examples of C1-4 alkylsulfinyl include methylsulfinyl, ethylsulfinyl, n-propylsulfinyl, isopropylsulfinyl, nbutylsulfinyl, isobutylsulfinyl, sec-butylsulfinyl, tertbutylsulfinyl, and like alkylsulfinyl groups whose alkyl moiety 20 is C1-4 straight-chain or branched-chain alkyl. Examples of arylsulfonyl ·include phenylsulfonyl, 1- naphthylsulfonyl, 2-naphthylsulfonyl, and the like. Examples of arylsulfinyl include phenylsulfinyl, 1- naphthylsulfinyl, 2-naphthylsulfinyl, and the like. 25 Examples of heterocyclic C1-4 alkyl include pyridylmethyl, pyrtdylethyl, pyridyl-n-propyl, benzothiazolylisopropyl, 1,2,4-triazol-1-yl-n~butyl, 2-thienyl-isobutyl, pyrazinyl-sec-butyl, pyridazinyl-tert-butyl, 2- benzothiazolylethyl, oxazolylisopropyl, isoxazoyl-sec-butyl, 30 thiazolylisobutyl, 8-quinolylmethyl, oxadiazolyl-n-propyl, and the like. The groups (1) to (23) represented by R4 may optionally be further svbstituted. The groups (1) to (17) represented by Rs may optionally be further substituted. The groups (1) to (17) I P 0 DB!i H-:Iepi2E@·enft£ -b~ @6lrrlfi.y .®pt~dilc&ly be further substituted. Examples 12 of the substituents for the groups (1) to (23) represented by R4 , the groups ( 1) . to ( 17) represented by R5 , and the groups ( 1) to (17) represented by R6 include nitro and cyano, as well as the above-mentioned halogen, C1-4 alkyl, C1-4 haloalkyl, C1-4 alkoxy, 5 C1-4 haloalkoxy, C2-4 alkenyloxy, C2-4 alkynyloxy, cyano C1-4 alkoxy, C3-B cycloalkyl, C3-8 cycloalkyl CJ-4 alkyl, C1-4 alkylsulfonyloxy, C1-4 alkylsulfinyloxy, arylsulfonyloxy, arylsulfinyloxy, Cl-4 alkylthio, C1-4 haloalkylthio, aryl, heterocyclic group, C1-12 alkyl, C1-4 alkoxy C1-4 alkyl, C1-4 haloalkoxy C1-4 alkyl, C2-4 alkenyl, 10 C2-4 alkynyl, C1-4 alkyl-carbonyl, cyano C1-s alkyl, C1-4 alkylsulfonyl, C1-4 alkylsulfinyl, arylsulfonyl, arylsulfinyloxy, heterocyclic C~4 alkyl, and the like. Of these, preferable substituents are halogen, C1-4 alkyl, C1-4 haloalkyl, C1-4 alkoxy, C1-4 haloalkoxy, and C1-4 alkylthio, and more preferab~e 15 substituents are chlorine, fluorine, trifluoromethyl, trifluoromethoxy, and methylthio. For example, aryl or heterocyclic group represented by R4, Rs, and R6 may have 1 to 5 above substituents .. Preferable substituted aryl groups are halogen-substituted aryl, C1-4 alkyl- 20 substituted aryl, C1-4 haloalkyl-substituted aryl, C1-4 alkoxysubstituted aryl, C1-4 haloalkoxy-substi~uted aryl, and C1-4 alkylthio-substituted aryl. More preferable substituted aryl groups are chlorine-substituted aryl, flUorine-substituted aryl, trifluoromethyl-substituted aryl, trifluoromethoxy-substituted 25 aryl, and methylthio-substituted aryl. Preferable substituted heterocyclic groups are halogensubstituted heterocyclic group, C1-4 alkyl-substituted heterocyclic group, C1-4 haloalkyl-substituted heterocyclic group, I Cl-4 alkoxy-substituted heterocyclic group, C1-4 haloalkoxy- 30 substituted heterocyclic group, and heterocyclic-substituted C1-4 alkylthio. The aryl or heterocyclic group of arylsulfonyl, arylsulfinyl, or C1-4 alkyl-substituted heterocyclic group represented by R4 , Rs, and R6 may also optionally have 1 to 5 I Po. D-815. H JSubsfi tuirifls al:B~.es,~ 1 7 :·. 0 8: 13 The salts of the compounds represented by Formula (1) may be any type of salts as long as they are agriculturally acceptable. Examples of the salts include hydrochloride salt, sulfate salt, nitrate salt, and like inorganic acid salts; 5 acetate salt, methanesulfonic acid salt, and like organic acid salts; sodium salt, potassium salt, and like alkali metal salts; magnesium salt, calcium salt, and like alkaline earth metal salts; dimethylarnrnonium, triethylarnrnonium, and like quaternary ammonium salts; and the like. 10 R1 , R2, and R3 of the formula representing the compound (1) of the present invention may be identical or different and each represent hydrogen, halogen, or C1-4 haloalkyl. R1 , R2, and R3 each preferably represent halogen. R1 more pre~erably represents fluorine or chlorine, and R2 and R3 each more preferably represent 15 chlorine. R1 , R2, and R3 each particularly preferably represent chlorine. A of the formula representing the compound (1) of the present invention represents 0, S(O)m, or NR6 , and A preferably represents 0 or S(O)m. 20 R4 of the formula representing the compound (1) of the 25 present invention is any one of the groups (1) to (23) defined as R4 in Claim 1. R4.is preferably any one of the groups (1) to (13) and (16) to (23) above. R4 is more preferably any one of the _groups (1) to (8), (10), (11), (13), (17), (20), and (22). The groups ( 1) to ( 17 )· represented by R4 of the formula representing the compound (1) of the present invention may further optionally be substituted. Two R4 groups, taken together, may form a ring, via or not via at least one heteroatom. Examples of the ring include C3-s 30 cycloalkyl, aryl, heterocyclic group, and the like. These C3-s cycloalkyl, aryl, and heterocyclic-groups are as defined above. Of these rings, aryl is preferable, and phenyl is more preferable. In this specification, a heteroatom refers to at least one atom selected from the group consisting of oxygen, sulfur, and I P' 0 D'E!l. Hilritib~enl 0- 2 01 5-. 17 : 08 14 R5 of the formula representing the compound of the present invention is any one of (1) to (17) defined as R5 in Claim 1. R5 is preferably any one of (1) to (3), (5) to (10), and (15). The groups (1) to (17) represented by R5 of the formula 5 representing the compound (1) of the present invention may further optionally be substituted. 10 R6 of the formula representing compound (1) of the present invention is any one of (1) to (17) defined ~s R6 in Claim 1. R6 is preferably any one of (1) to (3), (5) to (10), and (15). The groups ( 1) to ( 1 7) represented by R6 of the formula representing the compound (1) of the present invention may further optionally be substituted. When ~ is NR6, R5 and R6, taken together with the nitrogen, may form a 3- to 7-membered ring, via or not via at 15 least one heteroatom. The 3- to 7-membered ring refers to a hetero ring having at least one nitrogen atom. Examples thereof include aziridine, morpholine, azetidine, pyrrolidine, piperidine, and like saturated hetero rings; pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, and like heteroaryl groups; and the like. 20 W, X, Y, and Z may be identical or different, and each represent CR4 or N. It is preferabie that at least one of W, X, Y, and Z represents N, and the rest represent CR4 , or that W, X, Y, and Z each represent CR4 • It is more preferable that W, X, Y, Z each represent CR4 • 25 Of the compound (1) .of the· present invention, a preferable compound is a 2-substituted imidazole compound or a salt thereof in which Rl, R2, and R3 each represent halogen, R4 is any one of the groups (1) to (13) and (16) to (23), 30' two R4 groups, taken together, may form a ring, via or not via at least one heteroatom, the group represented by R4 above may further optionally be substituted, Rs is any one of (1) to (3), (5) to (10), and (15), I p 0- D-8-1. H:f:Ihe 2]fbupt aep~!Srelr~d lby I(Sa8ove may furtl)er optionally be 15 substituted, A represents 0 or S(O)m, m represents 0, 1, or 2, and W, X, Y, and Z are identical or different and each represent CR4 5 or N. A more preferable compound is a 2-substituted imidazole compound or a salt thereof in which R1 is fluorine or chlorine, R2 and R3 each represent chlorine, 10 R4 is any one of the groups (1) to (8), (10), (11), (13), (17), (20), and (22), two R4 groups, taken together, may form a ring, via or not via at least one heteroatom, the group represented by R4 above may further optionally be 15 substituted, R5 is any one of (1) to (3), (5) to (10), and (15), the group represented by R5 above may further optionally be substituted, A represents 0, and 20 W, X, Y, and Z are identical or different and each represent CR4 or N; or a 2-substituted imidazole compound or a salt thereof in which R1 represents fluorine or chlorine, R2 and R3 each represent chlorine, 25 R4 is any one of the groups (1) to (8), (10), (11), (13), (17), ( 2 0 ) , and ( 2 2 ) , two R4 groups, taken together, may form a ring, via or not via at least one heteroatom, the group represented by R4 above may further optionally be 30 substituted, R5 is any one of (1) to (3), (5) to (10), and (15), the group represented by R5 above may further optionally be substituted, A represents S (0) m, IP 0 D St. H ii i£t 0,- ll,Oor 220 lufd 1 7 : 0 8 16 W, X, Y, and Z are id~ntical or different and each represent CR4 or N. When the compound (1) has isomers such as optical isomers, stereoisomers, regioisomers, and the like, 5 any of the isomers and mixtures thereof are included within the scope of the compound (1). For example, when the compound (1) has optical isomers, the optical isomer separated from a racemic mixture is als.o included within the scope of the compound ( 1) . Each of such isomers may be obtained as a single compound by 10 known synthesis and separation means (e.g., concentration, 15 20 solvent extraction, column chromatography, and recrystallization). Method for preparing a 2-substituted imidazole compound or a salt thereof The compound (1) of the present invention is produced in accordance with the process described in the following Reaction Scheme 1. Reaction Scheme 1 Base I Solvent (2) ( 1) wherein R1 , R2 , R3, R4 , R5 , A, W, X, Y, Z, and n are·as defined above, and R7 represents a leaving group. As shown in Reaction Scheme 1 above, the compound (1) of the present invention is prepared by reacting a compound 25 represented by Formula (2) with a compound represented by Formula ( 3) . Examples of the leaving group represented by R7 include chlorine, bromine, iodine, and like halogen atoms, and alkyl IPO DE·LHiulib6Patel,Oar~8sL.J5Eonla1te,: f.lr&i the like. 17 In the reaction of the compound represented by Formula (2) and the compound represented by Formula (3), the proportions of these compounds used are not particularly limited, and may be suitably selected from a wide range. The latter is usually used 5 in an amount of about 1 to 5 moles, preferably about 1 mole,. per mole of the former. The above reaction is preferably carried out in the presence of a base. As the base, a wide variety of known bases may be used. Examples include sodium carbonate, potassium 10 carbonate, sodium bicarbonate, potassium bicarbonate, and like alkali metal carbonates; sodium hydroxide, potassium hydroxide, and like alkali metal hydroxides; sodium hydride, potassium hydride, and like alkali metal hydrides; sodium methoxide, sodium ethoxide, potassium tert-butoxide, and like alkali metal 15 alkoxides; and triethylamine, pyridine, and like organic bases. These bases may be used alone, or in a combination of two or more. The base may be used in a stoichiometric amount or more than the stoichiometric amount, with respect to the compound represented by Formula (2). The base is preferably used about 1 20 to 5 times the stoichiometric amount. When triethylamine, pyridine, or like an organic base is used, it can be used in large excess to serve also as a reaction solvent. The above reaction may be carried out in a suitable solvent or in the absence of solvent. When the reaction is 25 carried out in a solvent, usable solvents for the reaction are not limited· insofar as they are inert to the reaction. Examples· of solvents include n-hexane, ·cyclohexane, n-heptane, and like aliphatic or alicyclic hydrocarbons; benzene, chlorobenzene, toluene, xylene, and like aromatic hydrocarbons; methylene 30 chloride, 1,2-dichloroethane, chloroform, carbon tetrachloride, and like halogenated hydrocarbons; diethyl ether, tetrahydrofuran (THF), 1, 4-dioxane,. and like ethers; . N, N-dimethylformamide (DMF), and like amides; dimethylsulfoxide, and like sulfoxides; and the like. These solvents may be used alone or in a combination of two I P, 0 D B·!k .. Herr riibe'e-; JaQ rE?.qOilESi. 1 7 : 0 8 18 The reaction temperature of the above reaction, although not limited, is in the range of -20°C to the boiling point of the solvent used, and is preferably 0 to 25°C. The reaction time varies according to, for example, the reaction 5 temperature. The reaction is usually completed in about 0.5 to FJhollt. /.4 hollrs. The compound represented.by Formula (2) and the compound represented by Formula (3) used as starting materials in Reaction Scheme 1 above are known compounds or compounds easily 10 prepared by a known method. The compound of the present invention represented by Formula (1) or a salt thereof prepared according to the process shown in Reaction Scheme 1 above may be easily isolated from the reaction mixture and purified by known isolation and purification 15 techniques such as filtration, solvent extraction, distillation, recrystallization, and column chromatography. When the compound (1) has regioisomers, each regioisomer may be separated by a usual separation step such as silica gel chromatography. 20 Pest-Controlling Agent The compound (1) of the present invention may be used as an active ingredient of a pest-controlling agent. Examples of pest-controlling agents include agents (fungicides or virucides) for controlling plant diseases that cause problems in the 25 agricultural and horticultural fields; agents (agricultural and horticultural insecticide, miticides, nematicides, or soil insecticides) for controlling pests, mites, nematode, or soil pests that all cause problems iri the agricultural and horticultural fields, animal ectoparasite-controlling agent (e.g., 30 pulicide, ixodicide, and pedivulicideon), an~ the like. For use as an active ingredient of a pest-controlling agent, it is possible to use the compound (1) of the present invention as is with no additional components. However, it is usually preferable to use the compound by combining with a solid I PO- · 0'81.. H Cfarn9r; lLIDqu:i?dOc\£iiel7 G:t0..JI•Q• 29 5-Cl 126.7 (m, 2H), 7.35-7.32 (m, lH), 2. 72 (s, 3H); MS m/z: 349.03 (M+H). 2A CH CH Cl 5-Cl or Ph 1 0 122.2- DMSO-dG: 0 7.73-7.60 6-Cl 123.6 (m, 3H), 7. 55-7. 17 (m, SH); MS m/z: 411.09 (M+H). 28 CH CH Cl 6-Cl or Ph 1 0 133.8- DMSO-dG: 0 7.73-7.60 5-Cl 136.:> (m, 3H), 7.54-7.18 (m, SH). 3 CH CH Cl H Me 0 0 92.1- DMSO-d&: 6 7.G0-7.7G 94.2 (m, 2H), 7.45-7.42 (m, 2H), 2.92 (s, 3H); MS m/z: 315.04 (M+2H). 4A CH CH Cl 5-Cl or Me 1 2 DMSO-dG: 57.90-7.65 6-Cl (m, 2H), 7.42 (bs, lH), 3.49 (s, 3H). 48 CH CH Cl 6-Cl Or" Me 1 2 DMSO-dG: 57.70-7.66 5-Cl ( rri, 2H), 7.3,2 (d, J = 8.0 Hz, lH), 3.07 . (s, 3H). SA CH CH Cl 5-Cl or Me 1 1 DMSO-dG: 0 7.73-7.65 6-Cl (m, 2H), 7.34-7.32 (m, lH), 2. 72 (s, 3H). 58 CH CH Cl 5-Cl or Me 1 1 DMSO-dG: 0 7.73-7.64 6-Cl (m, 2H), 7.36-7.33 (m, lH), 2. 72 (s, 3H). 6 CH CH Cl H Acetyl 0 0 DMSO-'-dG: 0 7.72-7.70 (m, 2H), 7.48-7.46 '(m, 2H), 1. 42 (s, 3H). 7 CH CH Cl H Et 0 0 ,- DMSO-dG: ·o 7. 68-7. 63 (m, 2H), 7.31-7.29 (m, 2H), 3.35-3.31 (q, J = 7.2 Hz, 2H), 1.40 (t, J = 7.2 Hz, 3H). 8 CH CH Cl H Me 0 1 DMSO-:-d6: 0 7.68-7.66 (m, 2H), 7.45-7.42 (m, 2H), 2.92 (s, 3H). 9 CH CH Cl H i-Pr 0 0 DMSO-dG: 0 7.69-7.64 (m, 2H), 7.32-7.29 (m, 2H), 4.07-4.01 (m, lH), 1. 50-1.42 (m, 6H). lOA CH CH Cl 5-Cl or i-Pr 1 0 DMSO-dG: 0 7.74-7.65 6-Cl (m, 2H), 7.35-7.32 (m, lH), 4.08-4.01 . (m, lH), 1.49-1.42 (m, 6H); MS m/z: IP'O: DELH r- '") In n. llf"'t ·~ 41 .,.. • p.,,., 377.2 (M+H). ..lb .... "-"' ·"-" .... .._..,.~~,._, .II. F . J·O 30 ------------------------------------- lOB CH CH Cl 6-Cl or 5-Cl llA CH CH Cl 5-Cl or 6-Cl 118 CH CH Cl 6-Cl or 5-Cl 12 CH CH Cl 5-Me & 6-Me 13 CH CH Cl 4-Me & 7-Me i-Pr Et Et i-Pr i-Pr 14A CH CH Cl 5-CF3 or Me 6-CF3 148 CH CH 15 CH CH 16 CH CH 17A CH CH Cl 6-CF3 or Me 5-CF3 Cl 4, 6- (CF3) 2 Me & 5, 7- (CFJ) 2 Cl 4, 6- (CF3) 2 Et & 5,7-(CF3)2 Cl 5-F or Me 6-F 1 0 1 0 1 0 1 0 1 0 1 0 1 0 2 0 2 0 1 0 DMSO-d6: o 7.67-7.65 (rn, 2H), 7.36-7.33 (rn, 1H), 4.06-4.00 (rn, 1H), 1.49-1.42 (rn, 6H); MS rn/z: 377.2 (M+H) . DMSO-d6: o 7:74-7.65 (rn, 2H), 7.34-7.32 (rn, 1H), 3.36-3.30 (q, J = 7.2 Hz, 2H), 1.392 (t, J = 7.2 Hz, JH). DMS0-d6: o 7.66-7.64 (rn, 2H), 7.36-7.33 (rn, 1H), 3.35-3.30 (q, J = 7.2 Hz, 2H), 1.39 (t, J = 7.2 Hz, 3H); MS rn/z: 363.0 (M+H). DMSO-d6: o 7.52 (d, J = 8. 0 Hz, 1H), 7.43 (s, 1H), 7.22 (d, J = 8.0 Hz, 1H), 4.11-4.08 (rn, 1H), 1.41-1.40 (rn, 6H); MS rn/z: 356.9 (M+H). DMSO-d6: o 7.48 (d, J=7.6Hz, lH), 7.21-7.17 (rn, 1H), 7.13-7.11 (rn, 1H), 4.08-4.02 (rn, 1H), 2.53 (s, 3H), 1.50- 1.40 (rn, 6H); MS rn/z: 357.1 (M+H). CDCl3: o 7.94 (s, 1H), 7.75 (d, J = 8.4 Hz, 1H), 7.54- 7.52 (rn, 1H), 2.79 (s, 3H) .. CDCl3: o 7.93 (s, 1H), 7.74 (d, J = 8 . 4 Hz, 1H) , 7 . 57 (d, J = 8.4 Hz, 1H), 2.80 (s, 3H). CDCl3: o 8. 09 (s, lH),, '7.82 (s, lH), 2.85 (s, 3H). CDCl3: o 8.09 (s, 1H), 7.82 (s, 1H), 3.51-3.39 (rn, 2H), 1.51 (t, J = 7:2 Hz, 3H) . CDCl3: o 7.60-7.57 (rn, 1H), 7.37-7.34 H ;:ro ....... ...... ....... 1 I P 0. D E L .JI;.-~""YvRt---'~.~~..1-A-v··- ":.::•; ..,...,i !'-.v,-..A.+.. --, ~_,..;. --+...~. -~.:.:.r,. ,-:•- .- f~~.:.~to.J.I..,- -R--------'-----'----'------'----'----(-r'n-, ---1=H-) -,- :.7--.- 0"2----6-." 9-_7 __J 31 (m, 1H), 2.77 (s, 3H). 178 CH CH Cl 6-F or Me 1 0 CDCl): b 7.60-7.57 5-F (m, 1H), 7.40-7.37 ' (m, 1H), 7.06-7.00 (m, 1H), 2.76 (s, 3H). 18A CH CH Cl 5-F or Et 1 0 CDCl): b 7.60-7.57 6-F (m, 1H), 7.36-7.33 (m, lH), 7.02-6.97 - (m, 1H), 3.38-3.34 (rn, 2H), 1.48 (t, J = 7.2 Hz, 3H). 188 CH CH Cl 6-F or Et 1 0 CDCl3: b 7.60-7.56 5-F (m, 1H), 7.40-7.37 (m, 1H), 7.05-6.99 (m, 1H), 3.40-3.52 (m, 2H), 1. 49 (m, 3H). 19 CH CH Cl 5, 6-Cl2 Me 2 0 DMSO-d6: b 7.98 (d, J = 4. 0 Hz, 1H), 7.84 (s, 1H), 2.73 (s, 3H). 20 CH CH Cl 5, 6-Cl2 Et 2 0 122.1- DMSO-d6: b 7.99 (s, 123.1 1H), 7.85 (s, 1H), 3.37-3.31 (q, J = 7. 6 Hz, 2H), 1. 40 (t, J = 7. 6 Hz, 3H). 21 CH CH Cl H 2,6- 0 0 DMSO-d6: b 7.74 (m, Diehl oro 3H), 7.62-7.56 (m, phenyl 2H), 7.35-7.29 (m, 2H). 22 CH CH Cl H 2,5- 0 0 DMSO-d6: b 7.85 (bs, Diehl oro 1H), 7.77 (d, J = phenyl 7.6 Hz, 1H), 7. 71- 7.66 (m, 2H), 7.60- 7.52 (m, 2H), 7.43- 7.39 (m, 1H) . 23 CH CH Cl H· 3,4- 0 0 DMSO-d6: 0 7.98 (bs, Diehl oro 1H), 7.76 (d, J = phenyl 8.4 Hz, 2H), 7.77- 7.58 (m, 2H), 7.41- 7.32 (m, 2H). 24 CH CH Cl H 3- 0 0 DMSO-d6: 0 7.77 (d, Trifluor J = 8. 0 Hz, 1H), omethoxy 7.72-7.69 (m, 2H), phenyl 7.66-7.57 (m, 2H), 7.48-7.47 (m, 1H) ~ 7.41-7.32 (m, 2H). 25 CH CH Cl H 4- 0 0 DMSO-d6: 0 7.87-7.79 Trifluor (m, 2H), 7.76-7.74 omethoxy (m, 1H), 7. 68-7 •. 64 phenyl (m, 1H), 7.50-7.48 (m, 2H), 7.40-7.28 IPO DELH ... ...... ,.., ,· ..-... ...... ....... ... "' ..,. - .h, .A • (m, 2H). L (;. 'U JI.W ,;:;.. u· &. ;;;> .II.. I IJO 32 26 CH CH Cl H 4- 0 0 DMSO-d6: 6 7.73-7.60 Chloroph (m, 3H), 7.54-7.18 enyl (m, 5H). 27 CH CH Cl H 3- 0 0 DMSO-d6: 6 7.77-7.75 Chloroph (m, 2H), 7.66-7.63 enyl (m, 2H), 7.55-7.47 (m, 2H), 7.40-7.31 (m, 2H). 28 CH CH Cl H 2- 0 0 DMSO-d6: 6 7.77-7.66 Chloroph (m, 3H), 7.64-7.62 enyl (m, 1H), 7.54-7,49 (Ill, 1H), 7.46-7.30 (m, 3H). 29 CH CH Cl H Phenyl 0 0 CDCl3: 6 7.71-7.62 (m, 4H), 7.45-7.40 (m, 3H), 7.33-7.27 (m, 2H). 30 CH CH Cl 5-CF3 & Et 1 0 CDCl3: 6 7.93 (s, 6-CF3 1H), 7.73 (d, J = 8. 4 Hz, 1H), 7.56 (d, J = 8. 4 Hz, 1H), 3.49-3.38 (m, 2H), 1. 52-1.48 (m, 3H). 31 CH CH Cl H n-Pr 0 0 CDCl3: 6 7.69-7.65 (m, 2H), 7.31-7.24 (m, 2H), 3.366 (t, J = 7. 2 Hz, 2H), 1. 90-1.80 (m, 2H), 1.08 (t, J = 7.6 Hz,. 3H). 32 CH CH Cl H i-Pr 0 0 DMSO-d6: 6 7.68-7.64 (m, 2H), 7.32-7.29 (m, 2H), 3.98-3.91 (m, 1H), 1.83-1.72 (m,, 2H), 1. 49-1.41 (m, 3H), 1. 03-0.96 (m, 3H). 33 CH CH Cl H 3,3,3- 0 0 DMSO-d6: 6 7.71-7.67 Trifluor (m, 2H), 7.36-~.31 opropyl (m, 2H), 3.56-3.48 (m, 2H), 2.90-2.80 (m, 2H). 34 CH CH Cl 4-Me & Me 1 0 DMSO-d6: 6 7.50-7.48 7-Me (m, lH), 7.21-7.18 (m, 1H), 7.13-7.12 (m, lH), 2.74 (s,. 3H), 2.54 (s, 3H). 35 CH CH Cl 4-Me & Et 1 0 DMSO-d6: 6 7.54 (d, 7-Me J = 8. 0 Hz, 1H), 7.44-7.35 (m, 1H), 7.28 (d, J = 7.2 Hz, 1H), 3.62-3.56 (q, J = 7. 2 Hz, 2H), 1.37 (t, J = IPO DELH 1!- ~ ~ - ~..-.. ,,_ .. ..,, .. ,.. 7. 2 Hz, 3H) . .!!.. ,:;.u· li.U ,:;.u ;;;) .J. I bJIQ 33 36 CH CH Cl 5-Me & Acetyl 1 0 DMSO-dG: 6 7.50-7.43 6-Me (m, 1H), 7.40 (bs, 1H), 7.24-7.22 (m, 1H), 2.33 (s, 3H), 1.21 (s, 3H). 37 CH CH Cl 5-Me & Me 1 0 DMSO-dG: 6 7.55-7.50 6-Me (m, 1H), 7.40-7.44 (m, 1H), 7.13-7.11 (m, 1H), 2.71 (s, 3H), 2.43 (s, 3H).' 38 CH CH Cl 5-Cl & Acetyl 1 0 DMSO-dG: 6 7.63 (bs, 6=Cl 1H), 7.57 (<.1, J = 8. 8 Hz, 1H), 7.27- 7.24 (m, 1H), 1.18 (s, 3H). 39A CH CH Cl 4-Cl or Me 1 0 CDCl3: 6 7.66-7.64 7-Cl (m, 1H), 7.58-7.55 (m, 1H), 7.24-7.22 (m, 1H), 2.77 (s, 3H). 398 CH CH Cl 7-Cl or Me 1 0 CDCl3: 6 7.66-7.64 4-Cl (m, 1H), 7.58-7.55 (m, 1H), 7.28-7.27 (m, 1H), 2. 77 (s, 3H). 40A CH CH Cl 4-Cl or Et 1 0 CDCl3: 6 7.64-7.63 7-Cl (m, 1H), 7.58-7.56 (m, 1H), 7.24-7.21 (m, 1H), 3.40-3.34 (m, 2H), 1.48 (t, J = 7. 6 Hz, 3H). 408 CH CH Cl 7-Cl or Et 1 0 CDCl3: 6 7.66-7.66 4-Cl (m, 1H), 7.58-7.54 (m, 1H), 7.30-:-7 .. 25 (m, 1H), 3.40-3.28 (m, 2H), 1. 48 (m, 3H) . 41 CH CH Cl Fused Et 2 0 CDCl3: 6 8.07-8.06 J::?henyl (m, 2H), 7.98-7.91 (m, 2H), 7.47-7.43 (m, 2H), 3.47-3.42 (q, J = 7. 2 Hz, 2H), 1.53 (t, J = 7. 2 Hz, 3H). 42 CH CH Cl. Fused Me 2 0 CDCl3: 6 8.08-8.06 phenyl (m, 2H), 7.98-7.91 (m, 2H), 7.48-7.43 (m, 2H), 2.83 (s, 3H). 43 CH CH Cl H 2- 0 0 182.5- CD<;:l3: 6 7.74-7.65 Trifluor 183.2 (m, 4H), 7.34-7.31 omethoxy (m, 2H), 7.30-7.25 phenyl (m, 2H). 44 CH CH Cl 5-Me & Et 1 0 CDCl3: 6 7.57 (d, J 6-Me = 8. 4 Hz, 1H), 7.49 :tPO DELH ...... ,..... . -.,...., I'll .- ... -·. 1..-.. ...... (s,. 1H), 7.29 (d, J '..IIi. '- U· J!,;JUl· '- U• .i!o -J> .JI. I · u•u ,34 = 8.4 Hz, 1H) I 3.56-3.51 (q, J = 7.2 Hz, 2H) I 1. 37 (t, J = 7. 2 Hz, 3H). 45 CH CH Cl H n-Bu 0 0 CDCl3: 6 7.69-7.65 (m, 2H) I 7.31-7.24 (m, 2H) I 3.41-3.37 (q, J = 7. 2 Hz, 2H) I 1. 83-1.76 (m, 2H) I 1.59-1.46 (m, 2H) I 0.96 (t, J - 7.2 Hz, 3H). 46 CH N Cl 5-Cl & Me 1 0 CDCl3: 6 8.27 (d, J or or 6-Cl = 2.0 Hz, 1H) I 7.91 N CH (d, J = 2. 0 Hz, 1H) I 2.78 (s, 3H). 47 CH N Cl 5-Cl & Et 1 0 CDCl3: 6 8.27 (d, J or or 6-Cl = 2.0 Hz, 1H), 7.90 N CH (d, J = 2. 0 Hz, 1H) I 3.41-3.36 (q, J = 7. 2 Hz, 2H) I 1. 49 (t, J = 7.2 Hz, 3H). 48 CH CH Cl 4, 6-Clz & Me 2 0 84.2- CDCl3: 6 7.56 (d, J 5, 7-Clz 85.1 = 1. 6 Hz, 1H), 7.32 (d, J = 1. 6 Hz, 1H) I 2.997 (s, 3H). 49 CH CH Cl 4, 6-Clz & Et 2 0 104.1- COCl3: 6 7.56 (d, J 5, 7-Clz 105.1 = 2. 0 Hz, 1H), 7.31 (d, J = 2. 0 Hz, 1H) I 3.46-3.41 (q, J = 7. 6 Hz, 2H) I 1. 49 (t, J = 7.6 Hz, 3H). 50 CH CH Cl H 2- 0 0 CDCl3: 6 7.68-7.64 Methylpr (m, 2H) I 7.31-7.23 opyl (m, 2H) I 3.35-3.26 (m, 2H), 2.13-2.03 (m, 1H), 1.10-1.08 (m, 6H). 51A CH N Cl 5-Me or Me 1 0 CDCb: 6 8.15 (s, or or 6-Me 1H) I 7.73 (s, 1H) I N CH 2.77 (s, 3H) I 2.46 (s, 3H). 518 CH N Cl 6-Me or Me 1 0 CDCl3: 6 8.26 (s, or or 5-Me 1H) I 7.86 (s, lH), N CH ' 2.75 (s, 3H), 2.37 (s, 3H). 52A CH N Cl 5-Me or Et 1 0 CDCl3: 6 8.15 (s, or or 6-Me 1H), 7.72 (s, 1H), N CH 3.39-3.35 (q, J = 7.2 Hz, 2H), 1.48 (t, J = 7. 2 Hz, 3H). IPO D:ELH m-52I;l ~H l':h .-<;~-. q.:;-Me 410~ .. ..... EA;: 1 0 CDCl3: 6 8.31 (s, .ii.. "- ._, . .!!. ._, "-· 'Y'' ..!!. ..JI .JI. I uv· 35 or or 5-Me 1H) I 7.72 (s, 1H) I N CH 3.46-3.41 (m, 2H) I 1. 52-1.48 (m, 3H). 53 CH CH Cl 4-CF3 & Me 1 0 CDCl3: 6 7.85-7.83 7-CF3 (m, 1H) I 7.57-7.55 (m, 1H) I 7.34-7.30 (m, 1H) I 2.82 ( s, 3H). 54 CH CH Cl 4-CF3 & Et 1 0 CDCl3: 6 7.85-7.83 7-CF3 (m, iH) I 7.56-7.54 (m, 1H) I 7.33-7.29 (m, 1H) I 3.49-3.39 ' (m, 2H) I 1.51-1.48 . (m, 3H). 55 CH CH Cl 5, 6;-Me2 Me 2 0 CDCl3: 6 7.43 (d, J = 2. 4 Hz, 2H) I 2.76 (s, 3H) I 2.35 (d, J = 4. 4 Hz, 6H). 56 CH CH Cl 5-N02 & Et 1 0 CDCl3: 6 8.66 (d, J 6-N02 = 2.0 Hz, 1H) I 8.26-8.23 (m, 1H) I 7.70 (d, J = 8.8 Hz, 1H) I 3.45-3.40 (q, J = 7.2 Hz, 2H) I 1.51 (t, J = 7.2 Hz, 3H). 57 CH CH Cl 5-Br & Et 1 0 83.7- CDCl3: 6 7.81-7.79 6-Br 84.1 (m, 1H) I 7.54-7.50 (m, 1H) I 7.41-7.35 (m, 1H) I 3.40-3.34 (q, J = 7. 6 Hz, 2H) I 1. 48 (t, J = 7. 6 Hz, 3H). 58 CH CH Cl 5, 6-Cl2 2- 2 0 CDCl3: 6 7.73 (s, Methylpr 1H) I 7. 72 (s, 1H) I opyl 3.31-3.23 (m, 2H) I 2.12-2.02 (m, 1H) I 1. 25-1.07 (m, 6H). 59 CH CH Cl 5, 6-Cl2 n-Bu 2 0 CDCl3: 6 7.74 (s, 1H) I 7. 72 (s, 1H) I 3.38-3.34 (m, 2H) I 1. 82-1.75 (!J\, 2H) I 1. 66-1.45 (m, 2H) I 0.915 (t, J = 7.6 Hz, 3H). 60 CH CH Cl 5, 6-Cl2 i-Pr 2 0 CDCl3: 6 7.60 (bs, 2H) I 4.08-4.02 (m, . 1H) I .1. 46 (d, J = 6. 8 Hz, 6H). 61A CH CH Cl 5-F or n-Bu 1 0 CDCl3: 6 7.59-7.56 6-F (m, 1H) I 7.35-7.32 (m, 1H) I 7.01-6.96 (m, 1H) I 3.39-3.35 (m, 2H) I 1.83-1.75 (m, 2H) I 1. 53-1.46 IPO DE"LH '""· - ....... . ..., ..-.. - .. .... - (m, 2H) I 0.98-0.94 .!1. O::::.U·.· l.ll.J 0::::. U L :::>· ..ll.F . yo()· 36 (m, 3H). 618 CH CH Cl 5-F or n-8u 1 0 CDCl3: 0 7.58-7.55 6-F (m, 1H) I 7.39-7.37 (m, 1H) I 7.05-7.00 (m, 1H) I 3.39-3.34 (m, 2H) I 1. 82-1.75 (m, 2H) I 1. 53-1.46 (m, 2H) I 0.88-0.84 (m, 3H). bL CH CH Cl 4, :>, 6-Cl3 3,3,3,- 3 0 CDCl3: 0 7. 71 (s, & Trifluor 1H) I 3.59-3.54 (m, 5, G, 7-Cl:J opropyl 2H) I 2. 79=2.·71 (m, 2H). 63 CH CH Cl 4, 5, 6-Cl3 n-8u 3 0 CDCl3: 0 7.69 (s, & 1H) I 3.46-3.42 (q, 5, 6, 7-Cl3 J = 7. 2 Hz, 2H) I 1. 82-1.77 (m, 2H) I 1. 54-1.48 (m, 2H) I 0.975 (t, J = 7.2 Hz, 3H). 64 CH CH Cl Fused i-Pr 2 0 CDCl3: 0 8.07 (d, J phenyl = 5.2 Hz, 2H) I 7.98-7.91 (m, 2H) I 7.47-7.42 (m, 2H) I 4.27-4.20 (m, 1H) I 1. 69-1.52 (m, 6H). 65 CH CH Cl 5-MeO & Et 1 0 DMSO-d6: 0 7.54 (d, 6-MeO J = 8.8 Hz, 1H) I 7.24-7.18 (m, 1H) I 6.93-6.89 (m, 1H) I 3.80:-3.79 (m, 3H) I ~ 3.38-3.26 (m, 2H) I 1. 41-1.36 (m, 3H). 66A CH CH Cl 5-CF3 or Ethoxyet 1 0 DMSO-d6: 0 8.04 (s, 6-CF3 hyl 1H) I 7.88-7.86 (m, 1H) I 7.70-7.65 (m, 1H) I 3.74-3.70 (m, 2H) I 3.57-3.47 (m, 4H) I 1.12-1.07 (m, 3H). 668 CH CH Cl 6-CF3 or Ethoxyet 1 0 DMSO-d6: 7.91-7.66 5-CF3 hyl (m, 3H), 3.74-3.71 (m, 2H) I 3.58-3.55 (ml 2H) I 3.50-3.37 (m, 2H) I 1.12-1.09 (m, 3H). 67 CH CH Cl H Cy-Hex 0 0 DMSO-d6: 7.69-7.65 • (ml 2H) I 7.32-7.30 (m, 2H) I 3.96-3.91 (m, 1H) I 2.20-2.06 (m, 2H) I 1.72 (bs, 2H) I 1. 60-1.39 (m, 6H). 68 CH CH Cl H 2- 0 0 DMSO-d6: 7.72-7.68 Propynyl (m, 2H) I 7.35-7.32 IPO DELH - ·-- (m, 2H) I 4.23-4.20 ... LU ll:.Jl• Lll,;.ll :;:) ..II./ . ::.11·0 37 (m, 2H), 3.26-3.25 (m, 1H). 69 CH CH Cl 4, 6-Cl2 & 3,3,3,- 2 0 DMSO-d6: 7.69 (d, J 5, 7-Cl2 Trifluor = 1. 6 Hz, 1H), 7.58 opropyl (d, J = 1. 6 Hz, 1H), 3.58-3.53 (m, 2H), 2.89-2.83 (m, 2H). 70 CH CH Cl 5-F or 2- 1 0 CDCl3: 6 7.59-7.56 6-F Methylpr (m, 1H), 7.34-/.32' opyl (m, 1H), 7.01-6.96 (rn, HI), 3.34-3.24 (m, 2H), 2.11-2.05 (m, 1H), 1. 09-1.07 (m, 6H). 71 CH CH Cl 5-F & 1- 1 0 CDCl3: 6 7.59-7.55 6-F Methylpr (m, 1H), 7.40-7.32 opyl (m, 1H), 7.05-6.96 (m, 1H), 4.06-3.98 (in, 1H), 1. 88-1.73 (m, 2H), 1. 45-1.42 . (m, 3H), 1. 33-1.28 (m, 3H). 72 CH CH Cl 5-F or 2- 1 0 CDCl3: 6 7.59-7.54 6-F Methylpr (m, 1H), 7.39-7.32 opyl (m, 1H), 7.04-6.96 (m, 1H), 3.30-3.25 (m, 2H), 2.11-2.04 (m, 1H), 1.12-1.08 (m, 6H). 73A CH CH Cl 5-F or 3,3,3,-. 1 0 CDCl3: 6 7.61-7.58 6-F Trifluor (m, 1H), 7.36-7.34 opropyl (m, 1H), 7.05-6.98 (m, 1H), 3.54-3.46 (m, 2H), 2.79-2.66 (m, 2H). 73B CH CH Cl 6-F or 3,3,3,- 1 0 CDCl3: 6 7.68-7.57 5-F Trifluor (m, 1H), 7.41-7.33 opropyl (m, 1H)·, 7.08-7.00 (m, 1H), 3.56-3.46 (m, 2H), 2. 79-2. 66 (m, 2H) . 74 CH CH Cl 5-F & i-Pr 1 0 C0Cl3: 6 7.80-7.76' 6-F (m, 1H), 7.40-7.33 (m, 1H), 7.06-6.98 (m, 1H), 4.44-4.43 (m, lH), l. 32-1.29 (m, 6H). 75 CH CH Cl 5-CF3 & 3,3,3,- 1 0 CDCl3: 6 7.95 (b~, 6-CF3 Tri;fluor 1H), 7.78-7.74 (m, opropyl 1H), 7.60-7.54 (m, 1H), 3.56-3.50 (m, 2H), 2.78-2.70 (m, 2H). 76 CH CH Cl 5, 6-Cl2 Ethoxyet 2 0 CDCl3: 6 7. 76 (bs, I:PO DE~LH 1 .......... 4 - "' - ....... hyl 2H), 3.99 (bs, 2H), .1. t. ll:JI'· .JLI!,;J O::.U..II.:> .II. I •VO 38. 3.77-3.75 (m, 2H), 3.48 (bs, 2H), ' 1. 40-1.36 (m, 3H). 77 CH CH Cl 4, 5, 6-Cl3 Et 3 0 CDCl3: iS 7.70 (s, & lH), 3.47-3.41 (q, 5, 6, 7-Cl3 J = 7. 6 Hz, 2H), 1. 49 (t, J = 7.6 Hz, 3H). 78 CH CH Cl 4, 5, 6-Cl3 i-Pr 3 ·o CDCl3: iS 7.70 (s, & 1H), 4.25-4.20 (m, 5, 6, 7-Cl3 2H), 1. 57-1.55 (m, 6H) . 79 CH CH Cl 5-F & Ethoxyet 1 0 CDCl3: iS 7.70-7.65 6-F hyl (m, 1H), 7.54-7.48 (m, 1H), 7.21-7.14 (m, 1H), 3.72-3.69 (m, 2H), 3.54-3.36 (m, 4H), 1.12-1.08 (m, 3H). 80 CH CH Cl 4-Cl & 3,3,3,- 1 0 CDCl3: iS 7.67-7.65 7-Cl Trifluor (dd, J = 2.0, 7.2 opropyl Hz, 1H), 7.57 (t, J = 9.2 Hz, 1H), 7.29-7.24 (m, 1H), 3.52-3.47 (m, 2H), 2.78-2.68 (m, 2H). 81A CH CH Cl 5-Cl or n-Pr 1 0 CDCl3: iS 7.63 (d, J 6-Cl = 2.0 Hz, 1H), 7.57 (d, J = 8. 8 Hz, 1H), 7.24-7.21 (dd, J = 2.0, 8.8 Hz, 1H), 3.37-3.33 (m, 2H), 1. 87-1.82 (m, 2H), 1.10-1.06 (m, 3H). 81B CH CH Cl 6-Cl or n-Pr 1 0 CDCl3: iS 7.65-7.63 5-Cl (m, 1H), 7.58-7.54 (m, 1H), 7.25-7.21 (m, 1H), 3.36-3.33 (m, 2H), 1.89-1.80 (m, 2H), 1.10-1.06 (m, 3H). 82 CH CH Cl 5-Cl & 1- 1 0 CDCl3: iS 7.66-7.63 6-Cl Methylpr (m, 1H), 7.58-7.54 opyl (m, 1H), 7.25-7.21 (m, 1H), 4.04-3.97 (m, 1H), 1. 89-1.71 (m, 2H), 1. 53.:_1. 43 (m, 3H), 1.10-1.02 (m, 3H). 83 CH CH Cl 5-Cl & n-Bu 1 0 CDCl3: iS 7.66-7.63 6-Cl (dd, J = 2.0, 8.4 Hz, lH), 7.58-7.54 (m, 1H), 7.25-7.21 (m, lH), 3.39-3.35 IP:O DEL H - ·- (m, 2H), 1. 83-1.75 ..ll.. "' ll,;.ll· Jl. II;;JI• .60J\.:::J> .!!;./ .. .:.JIO 39 (m, 2H), 1.58-1.47 (m, 3H), ·0.98-0.94 (m, 3H). 84A CH CH C1 5-C1 or 3,3,3,- 1 0 CDC13: i5 7.65 (d, J 6-C1 Trif1uor = 1. 6 Hz, 1H), 7.59 opropy1 (d, J = 8.4 Hz, 1H), 7.27-7.24 (m, 1H), 4.04-3.97 (m, 1H), 1. 89-1.71 (m, 2H), 3.56-3.44 . (m, 2H), 2.79-2.66 (m, 2H). 84B CH CH C1 6-C1 or 3,3,3,- 1 0 CDC13: i5 7.67-7.65 5-C1 Trif1uor (dd, J = 2.0, 7.2 opropy1 Hz, 1H), 7.60-7.55 (m, 1H), 7.30-7.24 (m, 1H), 3.54-3.44 (m, 1H), 2.78-2.66 (m, 2H). 85 CH CH C1 5-C1 & 2- 1 0 CQC13: i5 7.66-7.62 6-C1 Methy1pr (m, 1H), 7.58-7.55 opy1 (m, 1H), 7.24-7.20 (m, 1H), 3.30-3.27 (m, 2H), 2.13-2.03 (m, 1H), 1.10-1.07 (m, 6H). 86A CH CH C1 5-C1 or Ethoxyet 1 0 CDC13: i5 7.62 (d, J 6-C1 hy1 = 1. 6 Hz, 1H), 7.57 (d, J = 8. 8 Hz, 1H), 7.24-7.21 (dd, J = 1. 6, 8.8 Hz, 1H), 3.81-3.78 (m, 2H), 3.62-3.47 (m, ' 4H), 1.25-1.19 (m, 3H). 86B CH CH C1 6-Cl or Ethoxyet 1 0 CDCl3: i5 7.66 (d, J 5-Cl hy1 = 1. 6 Hz, 1H), 7.54 (d, J = 8. 4 Hz, 1H) I 7.27-7.25 (m, 1H) I 3.80-3.78 (m, 2H) I 3.63-3.50 (m, 4H) I 1.25-1.14 (m, 3H). 87A CH CH C1 5-C1 or 2- 1 0 CDC13: i5 7.67 (d, J 6-C1 propyny1 = 2.0 Hz, 1H), 7.59 (d, J = 8.4 Hz, lH) I 7.29-7.25 (m, 1H) I 4.14-4.12 (m, 2H) I 2.28-2.26 (m, 1H). 87B CH CH C1 6-C1 or 2- 1 0 CDC13: i5 7. 67 (d, J 5-C1 propyny1 = 2.0 Hz, 1H), 7.59 (d, J = 8. 4 Hz, 1H), 7.29-7.27 (m, 1H), 4.14-4.12 (m, IPO: DELH ·- 2H), 2.28-2.27 (m, II;, ~u o.U' t:;.U .li. :::;. J. I • L:JI 0· 40 ----- ·---- .-------------------------------------------------------------------------------------- 1H). 88 CH CH Cl 5-Cl & cyclopro 1 0 CDCl3: 6 7.67-7.62 6-Cl pylmethy (m, 1H) I 7.58-7.53 1 (m, 1H) I 7.24-7.21 (m, 1H) I 3.33-3.30 (m, 2H) I 1.28-1.24 (m, 1H) I 0.68-0.61 (m, 2H) I 0.:?9-0.36 (m, 2H). 89A CH CH · Cl 5-Cl or 2- 1 0 CDC:l3: b 7.64 (d, J 6-Cl propenyl = 1. 6 Hz, 1H) I 7.58 (d, J :_; 8. 8 Hz, 1H) I 7.25-7.22 (m, 1H) I 9.07-5.97 (m, 1H) I 5.41-5.36 (m, 1H) I 5.21-5.01 (m, 1H) I 4.06-3.99 (m, 2H). 898 CH CH Cl 6-Cl or 2- 1 0 CDCl3: 6 7.66-7.64 5-Cl propenyl (dd; J = 2.0, 8.0 Hz, 1H) I 7.58-7.49 (m, 1H) I 7.28-7.22 (m, 1H) I 6.08-5.97 (m, 1H) I 5.41-5.36 (m, 1H) I 5.21-5.18 (m, 1H) I 4.06-3.94 (m, 2H). 90A CH CH Cl 5-CN or Et 1 0 CDCl3: 6 7.94 (d, J 6-CN = 1.2 Hz, 1H) I 7.74 (d, J = 8. 4 Hz, 1H) I 7.55-7.52 (dd, J = 1.2, 8.4 Hz, 1H) I 3.42-3.36 (q, J = 7. 2 Hz, 2H) I 1.49 (t, J = 7.2 Hz, 3H). 908 CH CH Cl 6-CN o:r;- Et 1 0 CDCl3: 6 7.96-7.94 5-CN (m, 1H) I 7.75-7.69 (m, 1H) I 7.59-7.52 (m, 1H) I 3.43 (m, 2H) I 1. 52-1.48 (m, 3H). 91A CH CH Cl 5-CN or Me 1 0 CDCl3: 6 7.95 (bs, 6-CN 1H) I 7.74 (d, J = 8.4 Hz, 1H) I 7.59- 7.53 (m, 1H) I 2.80 (s, 3H). 918 CH CH Cl 6-CN or Me 1. 0 CDCl3: 6 7.96 (bs, 5-CN 1H) I 7.75-7.70 (m, 1H) I 7.59-7.53 (m, 1H) I 2.80 (s, 3H), 928 CH CH Cl 5-CN or Ethoxyet 1 0 CDCl3: 6 8.01-7.93 6-CN hyl (m, 1H) I 7.77-7.66 (m, 1H) I 7.58-7:52 (m, 1H) I 3.83-3.79 . I.PO DELH .., - (m, 2H) I 3.63-3.53 ~ ... .t:.. II,;Ji· u· .t:.. 'U· ::::l> J;. I . ' 'JIO 41 . (rn, 4H), 1.23-1.19 (rn, 3H). 93A CH CH Cl 5-CN or n-Pr 1 0 CDCl3: b 7.94 (d, J 6-CN = 1.6 Hz, 1H), 7.74 (d, J = 8.4 Hz, 1H), 7.53 (dd, J = 1. 6 Hz, 8.4 Hz, 1H), 3.36 (t, J = 7.2 Hz, 2H) I 1. 91- 1.81 (rn, 21-i), 1.21 (t, J = 7. 2 Hz, JH). 93B CH CH Cl 6-CN or n-Pr 1 0 CDCl3: b 7.95-7.94 5-CN (rn, 1H), 7.69 (d, J = 8.4 Hz, 1H), 7.58-7.56 (dd, J = 1. 6 Hz, 8.4 Hz,· 1H), 3.40-3.35 (rn, 2H), 1.89-1.84 (rn, 2H), 1.21 (t, J = 7.6 Hz, 3H). 94 CH CH Cl 5-CN & n-Bu 1 0 CDCl3: b 7.95-7.94 6-CN (rn, 1H), 7.74-7.69 (rn, 1H), 7.58-7.52 (rn, 1H), 3.42-3.37 (rn, 2H) 1. 84-1.79 (rn, 2H), 1. 55-1.50 (rn, 2H), 0.97 (t, J = 8. 0 Hz, 3H). 95 CH CH Cl H Cyanornet 0 0 CDCl3: b 7.74-7.69 hyl (rn, 2H), 7.37-7.31 (rn, 2H), 4.25 (d, J = 16.4 Hz, 1H) I 4.12 (d, J = 16.4 Hz, 1H). 96 CH CH Cl 4, 6-Cl:Z & n-Pr 2 0 CDCl3: b 7.56 (d, J 5, 7-Cl2 = 2 .Hz, 1H), 7.31 (d, J = 1. 6 Hz, 1H) I 3.41 (t, J = 7.2 Hz, 2H), 1.90- 1.81 (rn, 2H), 1.08 (t, J = 7.2 Hz, 3H) . 97A CH CH Cl 4, 6-Cl2 or Ethoxye 2 0 CDCl3: b 7.56 (d, J 5, 7-Cl2 thyl = 1. 6 Hz, 1H), 7.31 (d, J = 1. 6 Hz, 1H), 3.82 (t, J' = 6. 0 Hz, 2H), 3.69- 3.54 (rn, 4H), 1.21 (t, J == 6.8 Hz, 3H). 97B CH CH Cl 5, 7-Cb or Ethoxye 2 0 CDCl3: b 7.56 (d, J 4,6-eC12 thyl = 1. 6 Hz, 1H), 7.31 (d, J = 1.. 6 Hz, 1H) I 3.82 (t, J = 6.0 Hz, 2H) I 3.69- IPO DELH .. ,t;.U .&.II.::.J! .::::U.!!.:!:I .JL/ • L:.ll tii· 42 3.54 (m, 4H), 1. 20 (t, J = 7.2 Hz, 3H). 98 CH CH Cl 4, 6-Cl2 & 1- 2 0 CDCl]: 6 7.56 (d, J 5, 7-Cl2 Methylpr = 1.6 Hz, 1H), 7.31 opyl (d, J = 1. 6 Hz, 1H), 4.15-4.07 (m, 1H), 1. 89-1.74 (m, 2H), 1. 57-1.46 (m, 3H), 1.24-1.08 (m, 3H). 99A CH CH Cl 4, 6-Cl2 or 2,2,2,- 2 0 CDCl3: i3 7.65 (d, J 5, 7-Cl2 Trifluor = 2. 0 Hz, 1H), 7.42 oethyl (d, J = 2. 0 Hz, 1H), 1. 28 (S'; 2H). 100 CH CH Cl 4, 6-Cl2 & n-Bu 2 0 CDCl3: 6 7.55 (d, J 5, 7-Cl2 = 1. 6 Hz, 1H), 7.31 (d, J = 1. 6 Hz, 1H), 3.43 (t, J = 7.2 Hz, 2H), 1.85- 1. 76 (m, 2H), 1.53- 1.47 (m, 2H) 1 0.97 (t, J = 7.2 Hz, 3H). 101 CH CH Cl 4, 6-Cl2 & Cyanomet 2 0 CDCl3: 6 7.61 (d, J 5, 7-Cl2 hyl = 2.0 Hz, lH) I 7.38 (d, J = 2. 0 Hz, 1H), 4.33 (bs 1 1H), 4.19 (bs, 1H). 102 CH CH Cl 5-Cl or Cyanomet 1 0 CDCl3: 6 7.29 (dl J A 6-Cl hyl = 2. 0 Hz, 1H) I 7.63 (d, J,; 8.8 Hz, 1H), 7.31 (dd, J = 2.0 Hz, 8.8 Hz, 1H), 4.21 (bs 1 1H), 4.08 (bs, 1H). 102 CH CH Cl 6-Cl or Cyanomet 1 0 CDCl3: 6 7.70 (d, J B 5-Cl hyl = 1. 6 Hz, 1H) I 7.63 (d, J = 8.8 Hz, 1H), 7.31 . (dd, J = 1. 6 Hz, 8.8 Hz, 1H), 4.21 (bs, 1H) I 4.07 (bs, 1H). 103 CH CH Cl 4-MeO or Me 1 0 CDCl3: 6 6 7.31 (d, A 7-MeO J = 8. 0 Hz, 1H), 7.19 (t, 8. 0 Hz, lH), 6.78 (d, J = 8 .. 0 Hz, 1H) I 1.01 (s, 3H), 2.81 (s, 3H) . 104 CH CH Cl 4'--EtO & Me 1 0 CDCl3: 6 7.29 (d, J 7-EtO = 8.0 Hz, 1H) I 7.16 (tl J = 8.0 Hz, 1H), 6.77 (d, J = 8.0 Hz, 1H), 4.36- IPO. OELH - ...... ...... ~ 1·-.. ..-. ,,.. "' '""' ""' 4.30 (q, J = 7.2 ..!!.. .(;, I!,;;.Ji• ll.:.JI .(;.Q .ll. :;:) .JI. I uo 43 Hz, 2H), 2.81 (s, 3H), 1. 54 (t, J = 7.2 Hz, 3H). 105 CH CH Cl 5, 6-Cl2 3,3,3,- 2 0 DMSO-d6: 6. 8.03 (s, Trifluor 1H), 7.88 (s, 1H), opropyl 3.55-3.50 (m, 2H), 2.87-2.79 (m, 2H). 106 CH CH Cl 5, 6-Cl2 2- 2 0 DMSO-d6: 0 7.99 (s, propenyl 1H), 7.85 (s, 1H), 6.05-5.97 (m, 1H), 5.42-5.37 (m, 1H), 5.19-5.17 (m, 1H), 4.04-4.02 (m, 2H). 107 CH CH Cl 5, 6-Cl2 1- 2 0 DMSO-d6: 0 7.98 (s, Methylpr 1H), 7.84 (s, 1H), opyl 3.98-3.90 (m, 1H), 1.82-1.71 (m, 2H), 1. 49-1.39 (m, 3H), 1. 01-0.96 (m, 3H). 108 CH CH Cl 5-S-Et or Me 1 0 CDCl3: 0 7.67-7.67 A 6-S-Et (m, 1H), 7.58-7.55 (m, 1H), 7.32-7.28 (m, 1H), 2.98-2.92 (m, 2H), 2.77 (s, 3H), 1.32-1.28 (m, 3H). 108 CH CH Cl 6-S-Et or Me 1 0 CDCh: 0 7.67-7.67 B 5-S-Et (m, 1H), 7.58-7.55 (m, 1H), 7.32-7.28 (m, 1H), 2.98-2.91 (m, 2H), 2.77 (s, 3H), 1.32-1.28 (m, 3H). 109 CH CH Cl 5-S-Et or Et 1 0 CDCl3: 0 7.68-7.66 A 6-S-Et (m, 1H), 7.58-7.55 (m, 1H), 7.28-7.26 (m, 1H), 3.40-3.34 (m, 2H), 2.98-2.93 (m, 2H), 1. 49-1.46 (m, 3H), 1.32-1.26 (m, 3H). .109 CH CH Cl 6-S-Et or Et 1 0 CDCl3: 0 7.68-7.66 B 5-S-Et (m, 1H), 7.58-7.54 (m, 1H), 7.32-7.28 (m, 1H), 3.39-3.34 (m, 2H), 2.98-2.91 (m, 2H), 1. 49-1.45 (m, 3H), 1. 32-1.26 (m·, 3H) . llO CH CH Cl 5-S-Et or n-Pr 1 0 CDCl3: 0 7.68-7.66 A 6-S-Et (m, 1H), 7.58-7.54 (m, 1H), 7.31-7.28. (m, 1H), 3.36-3.32 (m, 2H), 2.98-2.91 (m, 2H), 1. 87-1.81 IPO· o·ELH p ·~ ~ .-.. . -..,"""" .... ... - 1-.. '" (m, 2H), 1. 33-1.26 Jb .::;.u Jl.ij;;Jl (;,II.:JI ::;) .!I. I uo 44 (m, 3H), 1. 09-1.06 (m, 3H). 110 CH CH Cl 6-S-Et or n-Pr 1 0 CDCl3: 0 7.68-7.66 B 5-S-Et (m, lH), 7.58-7.54 (m, lH), 7.31-7.28 (m, lH), 3.37-3.32 (m, 2H), 2.98-2.91 (m, 2H), 1.87-1.81 (m, 2H), 1.33-1.26 (m, JH)' 1. 0~-l. (J~ (m, 3H). 111 CH CH Cl 5-S-EL OL" u-Bu 1 0 CDC13: 6 7.67-7.66 A 6-S-Et (m, lH), 7.57-7.54 (m, lH), 7.31-7.27 (m, lH), 3.39-3.35 (m, 2H), 2.98-2.91 (m, 2H), 1. 82-1.75 (m, 2H), 1.57-1.51 (m, 2H), 1.33-1.26. (m, 3H), 0.97-0.94 (m, 3H). 111 CH CH Cl 6-S-Et or n-Bu 1 0 CDCl3: ·o 7.67-7.66 B ' 5-S-Et (m, lH), 7.57-7.54 (m, lH), 7.31-7.27 (m, lH), 3.39-3.35 (m, 2H), 2.98-2.91 (m, 2H), 1. 82-1.75 (m, 2H), 1. 58-1.51 (m, 2H), 1. 32-1.26 (m, 3H), 1.19-0. 97 (m, 3H). 112 CH CH Cl 5-S-Et & 3,3,3,- 1 0 CDCl3: 0 7.72-7.67 6-S-Et Trifluor (m, 1H), 7.59-7.55 opropyl (m, lH), 7.34-7.28 (m, lH), 3.52.:..3.47 (m, 2H), 2.99-2.92 (m, 2H), 2.76-2.69 . (m, 2H), 1. 35-1.24 (m, 3H). 113 CH CH Cl 5-S-"Et & 2- 1 0 CDCl3: 0 7. 71-7.68 6-S-Et Cyanoeth (m, lH), 7.61-7.59 ' yl (m, lH), 7.35-7.32 (m, lH), 4.21-4.07 (m, 2H), 3.00-2.93 (m, 3H), 1.35-1.24 (m, 3H). 114 CH CH Cl 5-S-Et & 2- 1 0 CDCl3: 0 7.69-7.68 6-S-Et Propynyl (m, lH), 7.61-7.57 (m, lH), 7.33-7.28 (m, lH), 4.14-4.08 (m, 2H), 2.99-2.92 (m, 2H), 2.27-2.26 (m, lH), 1. 43-1.28 (m, 3H). 115 CH CH Cl 5-S-Me & Me 1 0 CDCl3: 0 7.58-7.55 . IPO DELH 6-S-1'1.e (m, 2H), 7.24-7.19 .:.. £1t.Jl l.ll.:.JI LU .IL :::> .IL I •. 1!;.:.11 0 45 (m, 1H), 2.76 (s, 3H), 2.53 (s, 3H). 116 CH CH Cl 5-S-Me or Et 1 0 CDCl3: 0 7.59-7.54 A 6-S-Me (m, 2H), 7.25-7.19 (m, 1H), 3.41-3.33 (m, 2H), 2.54 (s, 3H), 1. 57-1.41 (m, 3H). 116 CH CH Cl 6-S-Me or ~t 1 0 CDCl3: 0 7.58-7.53 B 5-S-Me (m, 2H), 7. 24·"7 .19 (m, 1H), 3.39-3.33 (Tl1, ?H)' /..52 (s, 3H), 1.49-1.42 (m, 3H). 117 CH CH Cl 5-S-Me or n-Pr 1 0 CDCl3: o 7".58-7.54 A 6-S-Me (m, 2H), 7.24-7.19 (m, 1H), 3.46-3.32 (m, 2H), 2.53 (s, 3H), 1.88-1.79 (m, 2H), 1.09-1.06 (m, 3H). 117 CH CH Cl 6-S-Me or n-Pr 1 0 CDCl3: 0 7.58-7.54 B 5-S-Me (m, 2H), 7.24-7.19 (m, 1H), 3.36-3.32 (m, 2H), 2.53 (s, 3H), 1.87-1.81 (m, 2H), 1.09-1.05 (m, 3H). 118 CH CH Cl 4-MeO & Et 1 0 CDCl3: 0 7.31-7.29 7-MeO (d, J = 8. 0 Hz, 1H), 7.19 (t, J = 8.0 Hz, 1H), 6.76 (d, J = 8. 0 Hz, 1H), 4.03 (s, 3H), ' 3.46-3.41 (q, J = ' 7. 6 Hz, 2H), 1. 45 (t, J = 7. 2 Hz, 3H). 119 CH CH Cl. H 2- 0 0 CDCl3: 0 7.69-7.65 Propenyl (m, 2H), 7.~2-7.26 (m, 2H), 6.09-5.99 (m, 1H), 5.04-5.35 (m, '1H), 5.20-5.17 (m, 1H), 4.08-4.02 (m, 2H). 120 CH CH Cl H Cyclopro 0 0 CDCl3: 0 7.69-7.64 pylmethy (m, 2H), 7.31-7.24 1 (m, 2H), 3.342- 3.324 (d, J = 7.2 Hz, 2H), 1.27-1.21 (m, 1H), 0.67-0.62 ., (m, 2H), 0.40-0.3'7 (m, 2H). 121 CH CH Cl 5, 6-Cl2 2- 2 0 DMSO-d6: 0 7.99 (bs, I Chloroph 1H), 7.94 (bs, 1H), IP·o. DELHI enyl 7.81-7.78 (m, 1H), t:. tJ! J.U .:::t:JJ.~ l. I . II.:.J ~· 46 7.70-7.68 (m, 1H) I 7.57-7.53 (m, 1H) I 7.48-7.44 (m, 1H). 122 CH CH Cl 5, 6-Cl2 2,6- 2 0 DMSO-d6: 0 7.96 (bs, Diehl oro 1H), 7.92 (bs, 1H) I phenyl 7.737 (bs, 1H) I 7. 71 (bs, 1H) I 7.62-7.58 (m, 1H). 123 CH CH Cl 5, 6-Cl2 2-CF3- 2 0 DMSO-d6: 0 7.97 (bs, phenyl 1H) I 7.94 (bs, 1H) I 7.90-7.88 (d, J = 7. 6 Hz, 1H) I 7.81- 7.73 (m, 2H). 124 CH CH Cl 5, 6-Cl2 4-CF30- 2 0 DMSO-d6: 0 7.98 (bs, phenyl 1H) I 7.93 (bs, 1H) I 7.83-7.81 (m, 2H) I 7.52-7.50 (m, 2H). 125 CH CH Cl 4-0CH2CN & Me 1 0 DMSO-d6: 0 7.17-7.13 7-0CH2CN (m, 2H) I 6.87 (bs, 1H) I 5.43 (bs, 2H) I 4.43 (s, 2H). 126 CH CH Cl 4-0CH2CN & Cyanomet 1 0 DMSO-d6: 0 7.22 (bs, 7-0CH2CN hyl 2H); 6.95 (bs, 1H) I 5.41 (s, 2H) I 2.78 (s, 3H). 127 CH CH Cl 4-0CH2CN & 3,3,3,- 1 0 DMSO-d6: 0 7.12-7.08 7-0CH2CN Trifluor (m, 1H) I 6.82 (bs, opropyl 1H) I 5.45 (bs, 2H) I 3.48-3.35 (m, 2H) I 2.85-2.81 (m, 2H). 128 CH CH Cl 5-S-Et & 2- 1 0 CDCl3: 0 7.59-7.56 6-S-Et Propynyl (m, 2H) I 7.24-7.22 ,- (m, 1H) I 4.14-4.12 (m, 2H) I 2.52 (s, 3H) I 2.27-2.26 (m, 1H) . 129 CH CH Cl 5-S-Et & 3,3,3,- 1 0 CDCl3: 0 7.64-7.55 6-S-Et Trifluor (m, 2H) I 7.22-7.21 opropyl (m, 1H) I 3.52-3.45 (m, 2H) I. 2.79-2.67 (m, 2H) I 2.53 (s, 3H). 130 CH CH Cl 5-S-Et & Cyanomet 1 0 CDCl3: 0 7.61-7.60 6-S-Et hyl (m, 2H) I 7.28 (bs, 1H) I 4.25-4.20 (m, 1H) I 4.15-4.07 (m, 1H) I 2.53 (s, 3H). 131 CH CH Cl 5-S-Et & 2- 1 0 CDCl3: 0 7.72-7.54 6-S-Et Methylpr. (m, 2H) I 7.31-7.27 opyl (m, 1H) I 3.31-3.27 (m, 2H) I 3.00-2.91 (m, 3H) I 2.09-2.06 (m, 1H) I 1.29-1.28 (m, 2H) I 1.19-1.07 (m·, 6H). IPO DELH •• 13~ A(H <;\! ·.fb 1 ~-S-~t7& •. r-..9'clopro 1 0 CDCl3: 0 7.68-7.66 .II.. '" '1-' • '1-' "'"'"" ..;; ... i£ J'V' 47 6-S-Et pylmethy (m, 1H), 7.58-7.54 1 (m, 1H), 7.32-7.28 (m, 1H), 3.33-3.30 (m, 2H), 2.98-2.92 (m, 2H), 1. 57-f. 21 (m, 4H), 0.67-0.62 (m, 2H), 0.39-0.37 (m, 2H). 133 CH CH Cl 5-S-Et or 2- 1 0 CDCl3: 0 7.68-7.66 A 6-S-Et Propenyl (m, 1H), 7.59-7.55 (m, 1H), 7.32-7.27 (m, 1H), 6.08-5.99 (m, 1H), 5.41-5.36 (m, 1H), 5.36-5.18 (m, 1H), 4.06-4;01 (m, '2H), 2.99-2.92 (m, 2H), 1.31-:-1.25 (m, 3H). 133 CH CH Cl 6-S-Et or 2- 1 0 CDCl3: 0 7.68-7.67 B 5-S-Et Propenyl (m, 1H), 7.59-7.55 (m, 1H), 7.32-7.27 (m, 1H), 6.07-6.00 (m, 1H), 5.41-5.36 (m, 1H), 5.36-5.18 (m, 1H), 4.03-4.00 (m, 2H), 2.99-2.92 (m, 2H), 1.33-1.26 (m, 3H). 134 CH CH Cl 5-S-Et & 1- 1 0 CDCl3: 0 7.52-7.51 6-S-Et Methylpr (m, 1H), 7.42 (m, opyl 1H), 7.24 (d, J = 2.0 Hz, 1H), 3.91- 3.86 (m, 1H), 2.95- 2.89 (m, 2H), 1.80- 1.68 (m, 2H), 1. 45- 1.43 (m, 3H), 1.30- 1.26 (m, 3H), 1.05- 1.02 (m, 3H). 135 CH CH Cl 4, 5-Fz & Me 2 0 DMSO-d6: 0 7.57-7.48 6, 7-Fz (m, 1H), 7.41-7.34 (m, 1H), 2.75 (s, 3H). 136 CH CH Cl 4, 5-Fz & Et 2 0 DMSO-d6: 0 7.38-7.35 6, 7-Fz (m, 1H), 7.11-7.04 ·(m, 1H), 3.45-3.39 (q, J = 7. 6 Hz, 2H), 1. 49 (t, J = 7. 6 Hz, 3H) . 137 CH CH Cl 4-0CHzCN & Et 1 0 DMSO-d6: 0 7.16-7.09 7-0CHzCN (m, 2H), 6.85-6.83 (m, 1H), 5.39 (s, 2H), 3.30-3.25 (m, 2H), 1. 37-1.34 (m, 3H). 138 CH CH Cl 4-0CHzCN & 3,3,3,- 1 0 DMSO-d6: 0 7.12-7.08 IPO DELH -~ 7-0CHzCN T:tifluor (m, 2H), 6.82 (bs, I. t:. li,;;J· U' t:.O ::Jj. ..L I . L:.IO 48 opropyl lH) I 5.45 (s, 2H) I 3.49-3.35 (m, 2H) I 2.85-2.79 (m, 2H). 139 CH CH Cl 4-0CH2CN & 2- 1 0 CDClJ: 6 7.46-7.44 7-0CH2CN Propynyl (m, 1H) I 7.24-7.22 (m, 1H) I 6.95-6.93 (m, 1H) I 5.40-5.36 (m, 1H) I 5.30-5.26 (m, 2H) I 4.19-4.09 (m, 2H) I 2.27-2.25 (m, 1H). 140 CH CH Cl 4-EtO & 3, J,J, <• 1 0 mmo d6: 6 7.30-7.27 7-EtO Trifluor (m, 1H) I 7.25-7.23 opropyl (m, 1H) I 6.90-6.88 (m, 1H) I 4.00 (bs, 2H) I 3.53-3.46 (m, 2H) I 2.87-2.79 (m, 2H) I 1. 29-1.18 (m, 3H). 141 CH CH Cl 5-N02 & 2- 1 0 DMSO-d6: 6 8.45-8.47 6-N02 Methylpr (m, 1H) I 8.23-8.21 opyl (m, 1H) I 7.88-7.84 (m, 1H) I 3.40-3.29 (s, 2H) I 2.10-2.04 (m, 1H) I 1. 04-1.02 (m, 6H). 142 CH CH Cl 5-N02 or Ethoxyet 1 0 DMSO-d6: 6 8.31 (d, A 6-N02 hyl J = 2. 4 Hz, 1H) I 8.08 (dd, J = 2.4 Hz, 8.8 Hz, 1H) I >· 7.62 (d, 8. 8 Hz, 1H) I 3.72-3.69 (m, 2H) I 3.54-3.53 (m, 4H) I 1.09 (t, J = 6. 8 Hz, 3H). 142 CH CH Cl 6-N02 or Ethoxyet 1 0 DMSO-d6: 6 8.41 (d, B 5-N02 · hyl J = 2. 0 Hz, 1H), 8.24 (dd, J = 2. 0, 8.4 Hz, 1H), 7.87 (dd, J = 2.0, 8.4 Hz, 1H), 3.73 (t! J = 6.4 Hz, 2H), 3.57 f (t, J = 6. 0 Hz, 2H), 3.49 (q, J = 6.4 Hz, 2H), 1.10 (t, J = 6.0 Hz, 3H). 143 CH CH Cl 5-N02 & 1- 1 0 DMSO-d6: 6 8.31 (bs, 6-N02 Methylpr 1H) I 8.16-8.14 (dd, opyl J = 2.2, 8. 8 Hz, 1H) I 7.76 (d, J = 8.8 Hz, 1H), 3.90 (bs, 1H) I 1.78-1.73 (m, 2H) I 1.44-1.42 (m, 3H) I 1. 02-0.98 (m, 3H). We Claim 1. A 2-substituted imidazole compound. represented by Formula (1): 5 or a salt thereof, wherein R1, R2, and R3 are identical or different and each represent hydrogen, halogen, or C1-4 haloalkyl, R4. represents (1} hydrogen, 10 (2) nitro, (3) cyano, (4) halogen, ( 5) C1-4 alkyl, (6} C1-4 haloalkyl, 15'- (7) C1-4 alkoxy, ( 8) C1-4 haloalkoxy, ( 9) benzyloxy, (10) benzylthio, (11) C~-4 alkenyloxy, 20 (12) C2-4· alkynyloxy, (13) cyano C1-4 alkoxy, (14) C3-s cycloalkyl, ( 15) C3-s cycloalkyl C1-4 alkoxy, ( 16) C1-4 alkylsulfonyloxy, 25 (17) c~4 alkylsulfinyloxy, (18) arylsulfonyloxy, ( 19) arylsulfinyloxy, (20) C1-4 alkylthio, (21) C1-4 haloalkylthio, IPO DELKI 20-10-201S 17:0& 89 ~-- . (·22) aryl, or (23) heterocyclic group, two R4 groups, taken together, may form a ring, via or not via at least one heteroatom, 5 the groups (1) to (23) represented by R4 may optionally be further substituted,····'"" Rs represents ( 1) C1-12 alkyl, (2) C1-12 haloalkyl, 10 (3) C1-4 alkoxy C1-4 alkyl, (4) C1-4 haloalkoxy C1-4 alkyl, (5) C2-4 alkenyl, (6) C2-4 alkynyl, (7) C3-s cycloalkyl, 15 (8) C3-s cycloalkyl C1-4 alkyl, (9) C1-4 alkyl-carbonyl, (10) cyano C1-s alkyl, (11) C1-4 alkylsulfonyl, (12) C1-4 alkylsulfinyl, 20 (13) arylsulfonyl, (14) arylsulfinyl, ( 15) aryl, ( 16) heterocyclic group, or (17) heterocyclic-substituted· C1-4 alkyl, 25 the groups ( 1) to (1 7) represented by R5 may optionally be further substituted, A rep.r esents 0, S (O)m, or NR6 , wherein R6 represents (1) C1-12 alkyl, 30 (2) C1-12 haloalkyl, (3) C1-4 alkoxy C1-4 alkyl, ( 4) C1-4 haloalkoxy C1-4 alkyl, (5) C2-4 alkenyl, (6) C2-4 alkynyl, I 1P 0· D. E3!Q. H lP ) 2