DIARYLIMIDAZOLE COMPOUND AND HARMFUL ORGANISM CONTROL AGENT

Abstract

The present invention provides a compound represented by formula (I) or salt thereof (in the formula, A.sup.1 and A.sup.2 each independently represents a nitrogen atom or the like, B.sup.1, B.sup.2, B.sup.3 and B.sup.4 each independently represents a carbon atom or nitrogen atom, X.sup.1 represents an unsubstituted or substituted C1-6 alkyl group or the like, n represents a number of X.sup.1 and represents an integer of 0-4, R.sup.1 represents a halogeno group or the like, R.sup.2 represents an unsubstituted or substituted C1-6 alkyl group or the like, m represents a number of the oxide group bonding with the nitrogen atom which does not bond with R.sup.2 on the imidazole ring, and represents 0 or 1, R.sup.3 represents a hydrogen atom or the like, Ar represents an unsubstituted or substituted C6-10 aryl group.

##STR00001##

Claims

1. A compound represented by formula (I) or salt thereof. ##STR00024## in formula (I), A.sup.1 and A.sup.2 each independently represents a nitrogen atom or CR.sup.3, provided that A.sup.1 and A.sup.2 do not simultaneously represent a nitrogen atom or simultaneously represent CR.sup.3, B.sup.1, B.sup.2, B.sup.3 and B.sup.4 each independently represents a carbon atom or a nitrogen atom, provided that when B.sup.1 is a nitrogen atom, B.sup.2 and B.sup.4 represent a carbon atom and B.sup.3 represents a carbon atom or a nitrogen atom, and when B.sup.1 is a carbon atom, B.sup.2 to B.sup.4 represent a carbon atom or a nitrogen atom except that two or more of B.sup.2 to B.sup.4 simultaneously represent a nitrogen atom, X.sup.1 represents an unsubstituted or substituted C1-6 alkyl group, unsubstituted or substituted C2-6 alkenyl group, unsubstituted or substituted C2-6 alkynyl group, hydroxy group, unsubstituted or substituted C1-6 alkoxy group, formyl group, unsubstituted or substituted C1-6 alkyl carbonyl group, unsubstituted or substituted C1-6 alkoxycarbonyl group, unsubstituted or substituted C1-6 alkyl aminocarbonyl group, mercapto group, unsubstituted or substituted C1-6 alkyl thio group, unsubstituted or substituted C1-6 alkyl sulfinyl group, unsubstituted or substituted C1-6 alkyl sulfonyl group, unsubstituted or substituted C3-8 cycloalkyl group, unsubstituted or substituted C6-10 aryl group, unsubstituted or substituted 3-6 membered heterocyclyl group, unsubstituted or substituted amino group, halogeno group, cyano group, or nitro group, n represents a chemically acceptable number of X.sup.1 and represents an integer of 0 to 4, when n is 2 or more, X.sup.1s may be the same or different, and when n is 2 or more, two X.sup.1s may bond together to form a ring, R.sup.1 represents a halogeno group, hydroxy group, cyano group, substituted C1-6 alkyl group, unsubstituted or substituted C1-6 alkoxy group, unsubstituted or substituted C1-6 alkyl thio group, unsubstituted or substituted C1-6 alkyl sulfinyl group, unsubstituted or substituted C1-6 alkyl sulfonyl group, unsubstituted or substituted C1-6 alkyl sulfonyloxy group, C1-6 alkyl aminocarbonyl group, C1-6 alkyl sulfoximino group or a group represented by —S(═O)(═N—R.sup.a)—R.sup.b, in the formula, le represents a hydrogen atom, cyano group, C1-6 alkyl group or unsubstituted or substituted C1-6 alkyl carbonyl group, R.sup.b represents a C1-6 alkyl group, R.sup.2 represents an unsubstituted or substituted C1-6 alkyl group, unsubstituted or substituted C2-6 alkenyl group, unsubstituted or substituted C2-6 alkynyl group, unsubstituted or substituted C3-8 cycloalkyl group, hydroxy group, unsubstituted or substituted C1-6 alkoxy group, formyl group, unsubstituted or substituted C1-6 alkyl carbonyl group, unsubstituted or substituted C1-6 alkoxycarbonyl group, or unsubstituted or substituted C1-6 alkyl sulfonyl group. R.sup.2 is a substituent bonding with any one of the two nitrogen atoms on the imidazole ring, m represents a number of the oxide group bonding with the nitrogen atom which does not bond with R.sup.2 on the imidazole ring, and represents 0 or 1, R.sup.3 represents a hydrogen atom, unsubstituted or substituted C1-6 alkyl group, unsubstituted or substituted C6-10 aryl group, halogeno group, cyano group or nitro group, Ar represents an unsubstituted or substituted C6-10 aryl group or unsubstituted or substituted 5-10 membered heteroaryl group.

2. The compound or salt thereof according to claiml, wherein formula (I) is formula (II) or formula (II), ##STR00025## in formula (II) and formula (III), X.sup.1, R.sup.1, R.sup.2, R.sup.3, B.sup.l, B.sup.2, B.sup.3, B.sup.4, n, m and Ar are as defined in formula (I).

3. A harmful organism control agent comprising as an active ingredient at least one selected from the group consisting of the compound and salt thereof defined in claim 1.

4. An insecticide or acaricide comprising as an active ingredient at least one selected from the group consisting of the compound and salt thereof defined in claim 1.

5. An external parasite control agent comprising as an active ingredient at least one selected from the group consisting of the compound and salt thereof defined in claim 1.

6. An internal parasite control agent or expellent comprising as an active ingredient at least one selected from the group consisting of the compound and salt thereof defined in claim 1.

7. A harmful organism control agent comprising as an active ingredient at least one selected from the group consisting of the compound and salt thereof defined in claim 2.

8. An insecticide or acaricide comprising as an active ingredient at least one selected from the group consisting of the compound and salt thereof defined in claim 2.

9. An external parasite control agent comprising as an active ingredient at least one selected from the group consisting of the compound and salt thereof defined in claim 2.

10. An internal parasite control agent or expellent comprising as an active ingredient at least one selected from the group consisting of the compound and salt thereof defined in claim 2.

Description

EXAMPLES

[0378] The following provides Examples to explain the present invention more specifically. However, the present invention is not limited to the following examples.

Example 1

Synthesis of 2-(2-(ethylsulfonyl)-4-(trifluoromethyl)phenyl)-1-methyl-5-(4-(trifluoromethyl)phenyl)-1H-imidazole (Compound 1-3)

(Step 1)

Synthesis of 2-oxo-2-(4-(trifluoromethyl)phenyl)acetaldehyde oxime

[0379] ##STR00009##

[0380] 30 g (0.44 mol, 3.3 eq) of sodium ethoxide was dissolved in 700 mol of ethanol and coolded to 0° C. 25 g (0.13 mol, 1.0 eq) of p-(trifluoromethyl)acetophenone and 20 ml (d=0.87, 0.15 mmol, 1.1 eq) of isopentyl nitrite were added to the resulting solution, followed by sttiring for 5 hours at room temperature. The resulting reaction liquid was then concentrated under reduced pressure and a saturated ammonium chloride aqueous solution was poured to the resulting residue. After that, the mixture was extracted with 20%-methanol/dichloromethane and the resulting organic layer was dried with anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography to obtain 15 g of the objective compound (yield: 51%).

[0381] .sup.1H-NMR of the obtained compound is shown below:

[0382] .sup.1H-NMR (400 MHz, CDCl.sub.3): δ 8.45(br s, 1H), 8.14(m, 2H), 7.98(s, 1H), 7.72(m, 2H).

(Step 2)

Synthesis of 1-methyl-5-(4-(trifluoromethypphenyl)-1H-imidazole 3-oxid

[0383] ##STR00010##

[0384] 15 g (0.069 mol, 1.0 eq) of 2-oxo-2-(4-(trifluoromethyl)phenyl)acetaldoxime was dissolved in 300 ml of acetic acid followed by stirring at room temperature. 10 g (0.076 mol, 1.1 eq) of 1,3,5-trimethyl hexahydro-1,3,5-triazine was added to the resulting solution followed by stirring for 3 hours at room temperature. The resulting reaction liquid was then concentrated under reduced pressure and the obtained crude crystal was washed with 50%-ethyl acetate/normal hexane to obtain 11 g of the objected compound (yield: 66%).

[0385] .sup.1H-NMR of the obtained compound is shown below:

[0386] .sup.1H-NMR (400 MHz, CDCl.sub.3): δ 8.14(d, 11-1), 7.75(m, 2H), 7.50(m, 2H), 7.30(d, 1H), 3.66(s, 3H).

(Step 3)

Synthesis of 2-(2-fluoro-4-(trifluoromethyl)phenyl)-1-methyl-5-(4-(trifluoromethypplicnyl)-1H-imidazole 3-oxide (Compound 1-5)

[0387] ##STR00011##

[0388] 1.0 g (4.1 mmol, 1.1 eq) of 1-methyl-5-(4-(trifluoromethyl)phenyl)-1H-imidazole 3-oxide, 0.043 g (0.19 mmol, 5 mol %) of palladium acetate, 0.18 g (0.57 mol, 15 mol %) of tri(p-fluorophenyl)phosphine, 0.11 g (1.1 mmol, 30 mol %) of pivalic acid, and 1.0 g (7.4 mmol, 2.0 eq) of carbonic acid potassium were added to a reactor, followed by replacing the air with argon gas. 14 mol of anhydrous acetonitrile solution of 0.90 g (3.7 mmol, 1.0 eq) of 4-bromo-3-fluorobenzene trifluoride was added to the resulting mixture, followed by stirring over night at 70° C. The resulting reaction liquid was filtered over celite and concentrated under reduced pressure. The obtained crude crystal was washed with diethylether to obtain 1.1 g of the objective compound (yield: 73%).

[0389] .sup.1H-NMR of the obtained compound is shown below:

[0390] .sup.1H-NMR (400 MHz, CDCl.sub.3): δ 8.21(m, 1H), 7.80(m, 2H), 7.64(m, 111), 7.59(m, 2H), 7.57(m, 1H), 7.47(s, 1H), 3.57(d, 3H).

(Step 4)

Synthesis of 2-(2-fluoro-4-(trifluoromethyl)phenyl)-1-methyl-5-(4-(trifluoromethyl)phenyl)-1H-imidazole (Compound 1-4)

[0391] ##STR00012##

[0392] 1.1g (2.7 mmol, 1.0 eq) of 2-(2-fluoro-4-(trifluoromethyl)phenyl)-1-methyl-5-(4-(trifluoromethyl)phenyl)-1H-imida zole 3-oxide was dissolved in 30 ml of acetic acid followed by stirring at room temperature. 1.5 g (27 mmol, 10 eq) of electrolytic iron powder was then added to the resulting solution followed by stirring for 5 hours at 70° C. Te resulting reaction liquid was concentrated under reduced pressure, neutralized by a saturated aqueous solution of sodium hydrogen carbonate, followed by filtering over celite. After that, the resulting mixure was extracted with dichloromethane and the obtained organic layer was dried by adding anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to obtain 0.83 g of the objective compound (yield 83%).

[0393] .sup.1H-NMR of the obtained compound is shown below:

[0394] .sup.1H-NMR (400 MHz, CDCl.sub.3): δ 7.84(m, 1H), 7.74(m, 2H), 7.61(m, 1H), 7.58(m, 1H),7.51(m, 1H), 7.35(s, 1H), 3.61(d, 3H).

(Step 5)

[0395] Synthesis of 2-(2-(ethylsulfanyl)-4-(trifluoromethyl)phenyl)-1-methyl-5-(4-(trifluoromethyl)phenyl)-1H-imidazole (Compound 1-7)

##STR00013##

[0396] 0.53 g (1.4 mmol, 1.0 eq) of 2-(2-fluoro-4-(trifluoromethyl)phenyl)-1-methyl-5-(4-(trifluoromethypphenyl)-1H-imida zole was dissolved in 14 ml of N,N-dimethyl foimamide followed by stirring at room temperature. 0.72 g (80%, 6.8 mmol, 5.0 eq) of ethyl mercaptan sodium was then added to the resulting solution followed by stirring for 1 hour at 100° C. The resulting reaction liquid was cooled to room temperature followed by pouring water and extracted with ethyl acetate. The obtained organic layer was washed with brine, dried by adding anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure and the obtained residue was purified by silica gel column chromatography to obtain 0.30 g of the objective compound (yield: 50%).

[0397] .sup.1H-NMR of the obtained compound is shown below:

[0398] .sup.1H -NMR(400 MHz, CDCl.sub.3): δ 7.73(m, 2H), 7.60(m, 3H), 7.53(m, 2H), 7.33(s, 1H), 3.52(s, 3H), 2.94(q, 2H), 1.32(t, 3H).

(Step 6)

Synthesis of 2-(2-(ethylsulfonyl)-4-(trifluoromethyl)phenyl)-1-methyl-5-(4-(trifluoromethyl)phenyl)-1H-imidazole (Compound 1-3)

[0399] ##STR00014##

[0400] 0.27 g (0.63 mmol, 1.0 eq) of 2-(2-ethyl sulfanyl-4-(trifluoromethyl)phenyl)-1-methyl-5-(4-(trifluoromethyl)phenyl)-1H-imidazol e was dissolved in 7 ml of chloroform followed by stirring at 0° C. 0.31 g (70%, 1.3 mmol, 2.0 eq) of metachloroperbenzoic acid was added to the resulting solution followd by stirring for 2 hours at 0° C. The resulting reaction liquid was poured to a mixed solution of saturated aqueous solution of sodium hydrogen carbonate and saturated aqueous solution of sodium thiosulfate followed by extracting with chloroform. The obtained organic layer was washed with brine, dired by adding anhydrous magnesium sulfate and filtered. The filtrate was concentrated under redude pressure and the obtained residue was purified by silica gel column chromatography to obtain 0.15 g of the objective compound (yield: 51%).

[0401] .sup.11-1-NMR of the obtained compound is shown below:

[0402] .sup.1H-NMR(400 MHz, CDCl.sub.3): δ 8.47(m, 1H), 8.03(m, 1H), 7.73(m, 3H), 7.60(m, 2H), 3.47(q, 2H), 3.44(s, 3H), 1.26(t, 3H).

[0403] TABLE 1 to TABLE 9 show the compounds of the present invention produced by the same production procees of the above-described Examples. In addition, the physical properties of the comounds are shown in the column of “Physical Property”. As the physical properties, property, melting point (m.p.) or refraction index are shown.

[0404] In addition, in the tables, Ph represents phenyl group, Me represents methyl group, Et represents ethyl group, .sup.nPr represents normal propyl group, .sup.iPr represents isopropyl group, .sup.cPr represents cyclopropyl group, nBu represent normal butyl group, sBu represents sencondary butyl group and tBu represents tertial butyl group.

[0405] TABLE 1 shows the substituents of the compounds represente by formula (1).

##STR00015##

TABLE-US-00001 TABLE 1 No. R.sup.1 (X.sup.1)n Ar R.sup.2 R.sup.3 m Physical Property 1-1 SO.sub.2Et 4-CF.sub.3 5-CF.sub.3-pyridine-2-yl Me H 0 m.p. 145-148° C. 1-2 SEt 4-CF.sub.3 5-CF.sub.3-pyridine-2-yl Me H 0 viscous oil 1-3 SO.sub.2Et 4-CF.sub.3 4-CF.sub.3—Ph Me H 0 m.p. 144-147° C. 1-4 F 4-CF.sub.3 4-CF.sub.3—Ph Me H 0 m.p. 126-128° C. 1-5 F 4-CF.sub.3 4-CF.sub.3—Ph Me H 1 m.p. 229-231° C. 1-6 SEt 4-CF.sub.3 4-CF.sub.3—Ph Me Me 0 m.p. 96-101° C. 1-7 SEt 4-CF.sub.3 4-CF.sub.3—Ph Me H 0 m.p. 111-113° C. 1-8 SEt 4-CF.sub.3 3-CF.sub.3—Ph Me H 0 n.sub.D(22.0° C.)1.5454 1-9 SEt 4-CF.sub.3 2-CF.sub.3—Ph Me H 0 viscous oil 1-10 SEt — 4-CF.sub.3—Ph Me H 1 amorphous 1-11 SOEt — 4-CF.sub.3—Ph Me H 1 m.p.: 194-195° C. 1-12 SO.sub.2Et — 4-CF.sub.3—Ph Me H 1 m.p.: 131-132° C. 1-13 SEt — 4-CF.sub.3—Ph Me H 0 n.sub.D(22.2° C.)1.5962 1-14 SOEt — 4-CF.sub.3—Ph Me H 0 m.p.: 162-164° C. 1-15 SO.sub.2Et — 4-CF.sub.3—Ph Me H 0 m.p.: 205-208° C. 1-16 SO.sub.2Et 4-CF.sub.3 2-CF.sub.3—Ph Me H 0 m.p.: 124-125° C. 1-17 SO.sub.2Et 4-CF.sub.3 3-CF.sub.3—Ph Me H 0 m.p.: 165-166° C. 1-18 SOEt 4-CF.sub.3 4-CF.sub.3—Ph Me H 0 m.p.: 154-155° C. 1-19 SEt 4-CF.sub.3 4-Cl—Ph Me H 0 m.p.: 92-94° C. 1-20 SO.sub.2Et 4-CF.sub.3 4-Cl—Ph Me H 0 m.p.: 172-173° C. 1-21 SEt 4-CF.sub.3 4-.sup.tBu—Ph Me H 0 m.p.: 117-118° C. 1-22 SO.sub.2Et 4-CF.sub.3 4-.sup.tBu—Ph Me H 0 m.p.: 201-202° C. 1-23 SEt 4-CF.sub.3 4-CF.sub.3—Ph Et H 0 viscous oil 1-24 SO.sub.2Et 4-CF.sub.3 4-CF.sub.3—Ph Et H 0 m.p.: 109-110° C. 1-25 SEt 4-CF.sub.3 4-CF.sub.3—Ph Me Cl 0 m.p.: 140-142° C. 1-26 SEt 4-.sup.tBu 4-CF.sub.3—Ph Me H 1 m.p.: 200° C. up 1-27 SEt 4-.sup.tBu 4-CF.sub.3—Ph Me H 0 m.p.: 127-129° C. 1-28 SEt 4-CF.sub.3 4-CF.sub.3—Ph Me Br 0 m.p.: 140-141° C. 1-29 SO.sub.2Et 4-CF.sub.3 4-CF.sub.3—Ph Me Br 0 m.p.: 153-154° C. 1-30 SO.sub.2Et 4-.sup.tBu 4-CF.sub.3—Ph Me H 0 m.p.: 197-199° C. 1-31 OEt 4-CF.sub.3 4-CF.sub.3—Ph Me H 0 m.p.: 98-101° C. 1-32 SEt 3-CF.sub.3 4-CF.sub.3—Ph Me H 0 viscous oil 1-33 SO.sub.2Et 3-CF.sub.3 4-CF.sub.3—Ph Me H 0 amorphous 1-34 SOEt 3-CF.sub.3 4-CF.sub.3—Ph Me H 0 m.p.: 183-184° C. 1-35 SO.sub.2Et 4-CF.sub.3 4-OCF.sub.3—Ph Me H 0 m.p.: 140-142° C. 1-36 SO.sub.2Et 4-CF.sub.3 3,5-Cl.sub.2—Ph Me H 0 m.p.: 130-131° C. 1-37 SO.sub.2Et 4-CF.sub.3 3,5-F.sub.2—Ph Me H 0 m.p.: 127-131° C. 1-38 SO.sub.2Et 4-CF.sub.3 3,5-(CF.sub.3).sub.2—Ph Me H 0 m.p.: 158-162° C. 1-39 SO.sub.2Et 4-CF.sub.3 3,4-Cl.sub.2—Ph Me H 0 m.p.: 150-151° C. 1-40 SO.sub.2Et 4-CF.sub.3 2,6-Cl.sub.2—Ph Me H 0 m.p.: 160-162° C. 1-41 SO.sub.2Et 4-CF.sub.3 3-Cl—Ph Me H 0 m.p.: 127-134° C. 1-42 SO.sub.2Et 4-CF.sub.3 4-F—Ph Me H 0 m.p.: 154-156° C. 1-43 SO.sub.2Et 4-CF.sub.3 Ph Me H 0 m.p.: 149-152° C. 1-44 SO.sub.2Et 4-CF.sub.3 4-OMe—Ph Me H 0 m.p.: 170-171° C. 1-45 SO.sub.2Et 4-CF.sub.3 4-Me—Ph Me H 0 m.p.: 180-181° C. 1-46 SO.sub.2Et 4-CF.sub.3 6-CF.sub.3-pyridine-3-yl Me H 0 m.p.: 165-167° C. 1-47 SO.sub.2Et 4-CF.sub.3 5-CF.sub.3-pyridine-3-yl Me H 0 m.p.: 126-129° C. 1-48 SO.sub.2Et 4-CF.sub.3 6-CF.sub.3-pyridine-2-yl Me H 0 m.p.: 141-142° C. 1-49 SO.sub.2Et 4-CF.sub.3 2-Cl-pyridine-4-yl Me H 0 m.p.: 162-164° C. 1-50 SO.sub.2Et 4-CF.sub.3 4-CF.sub.3—Ph Me Cl 0 m.p.: 82-85° C. 1-51 SO.sub.2Et 4-CF.sub.3 4-CF.sub.3—Ph .sup.cPr H 0 amorphous 1-52 SO.sub.2Et 4-CF.sub.3 4-NO.sub.2—Ph Me H 0 m.p.: 170-172° C. 1-53 SO.sub.2Et 4-CF.sub.3 4-NH.sub.2—Ph Me H 0 m.p.: 208-210° C. 1-54 SO.sub.2Et 4-CF.sub.3 4-Br—Ph Me H 0 m.p.: 192-195° C. 1-55 SO.sub.2Et 4-CF.sub.3 4-Br—Ph Me Br 0 m.p.: 182-184° C. 1-56 SO.sub.2Et 4-CF.sub.3 3-Cl-5-CF.sub.3- Me H 0 m.p.: 128-129° C. pyridine-2-yl 1-57 SO.sub.2Et 4-CF.sub.3 4-CHF.sub.2O—Ph Me H 0 m.p.: 149-151° C. 1-58 SO.sub.2Et 4-CF.sub.3 4-CF.sub.3-pyridine-2-yl Me H 0 m.p.: 164-169° C. 1-59 SO.sub.2Et 4-CF.sub.3 4-CF.sub.3-6-(4- Me H 0 m.p.: 206-209° C. CF.sub.3-pyridine-2- yl)pyridine-2-yl 1-60 SO.sub.2Et 4-F 4-CF.sub.3—Ph Me H 0 m.p.: 171-172° C. 1-61 SEt 2-CF.sub.3 4-CF.sub.3—Ph Me H 0 viscous oil 1-62 SO.sub.2Et 2-CF.sub.3 4-CF.sub.3—Ph Me H 0 viscous oil 1-63 SOEt 2-CF.sub.3 4-CF.sub.3—Ph Me H 0 amorphous 1-64 SEt 4-CF.sub.3 1-CF.sub.3—1H-pyrazol-4-yl Me H 0 m.p.: 120-121° C. 1-65 SO.sub.2Et 4-CF.sub.3 1-CF.sub.3—1H-pyrazol-4-yl Me H 0 m.p.: 177-179° C. 1-66 SO.sub.2Et 4-CF.sub.3 2-F-4-CF.sub.3—Ph Me H 0 m.p.: 121-126° C. 1-67 SO.sub.2Et 4-CF.sub.3 2-SEt-4-CF.sub.3—Ph Me H 0 m.p.: 171-172° C. 1-68 SO.sub.2Et 4-CF.sub.3 2-SO.sub.2Et-4-CF.sub.3—Ph Me H 0 m.p.: 154-156° C. 1-69 SO.sub.2Et 4-CF.sub.3 2-CN-4-CF.sub.3—Ph Me H 0 m.p.: 142-144° C. 1-70 SEt 3-CF.sub.3 4-CF.sub.3—Ph Me H 0 m.p.: 134-136° C. 1-71 SOEt 3-CF.sub.3 4-CF.sub.3—Ph Me H 0 m.p.: 165-168° C. 1-72 SO.sub.2Et 3-CF.sub.3 4-CF.sub.3—Ph Me H 0 m.p.: 200° C. up 1-73 SO.sub.2Et 4-CF.sub.3 4-CF.sub.3—Ph CF.sub.3 H 0 m.p.: 155-156° C. 1-74 SO.sub.2Et 4-CF.sub.3 4-CF.sub.3—Ph C(.sup.2H).sub.3 H 0 m.p.: 138-141° C. 1-75 SEt 4-CF.sub.3 2-Cl-4-CF.sub.3—Ph Me H 0 m.p.: 126-128° C. 1-76 SO.sub.2Et 4-CF.sub.3 2-Cl-4-CF.sub.3—Ph Me H 0 n.sub.D(19.0° C.)1.5309 1-77 SO.sub.2Et 4-CF.sub.3 4-(perfluoropropan-2-yl)Ph Me H 0 m.p.: 214-217° C. 1-78 SEt 4-CF.sub.3 4-C.sub.2F.sub.5—Ph Me H 0 m.p.: 99-101° C. 1-79 SO.sub.2Et 4-CF.sub.3 4-C.sub.2F.sub.5—Ph Me H 0 m.p.: 155-157° C. 1-80 SEt 4-CF.sub.3 4-(1,1,1,3,3,3-F.sub.6-2-OMe- Me H 0 n.sub.D(19.8° C.)1.525 propan-2-yl)Ph 1-81 SO.sub.2Et 4-CF.sub.3 4-(1,1,1,3,3,3-F.sub.6-2-OMe- Me H 0 m.p.: 183-185° C. propan-2-yl)Ph 1-82 SO.sub.2Et 4-CF.sub.3 4-CF.sub.3—Ph CHF.sub.2 H 0 m.p.: 133-135° C. 1-83 SO.sub.2Et 4-CF.sub.3 4-SCF.sub.3—Ph Me H 0 m.p.: 140-143° C. 1-84 SO.sub.2Et 4-CF.sub.3 4-SOCF.sub.3—Ph Me H 0 m.p.: 120-122° C. 1-85 SO.sub.2Et 4-CF.sub.3 6-Cl-pyridine-3-yl Me H 0 m.p.: 168-170° C. 1-86 SO.sub.2Et 4-CF.sub.3 2-CF.sub.3-pyrimidin-5-yl Me H 0 m.p.: 170-174° C. 1-87 SO.sub.2Me 4-CF.sub.3 4-CF.sub.3—Ph Me H 0 viscous oil 1-88 SO.sub.2Et 4-CF.sub.3 4-SO.sub.2CF.sub.3—Ph Me H 0 m.p.: 132-134° C. 1-89 SO.sub.2Et 4-CF.sub.3 2,2-F.sub.2-benzo[1,3]dioxol- Me H 0 m.p.: 106-108° C. 5-yl 1-90 SO.sub.2Et 4-CF.sub.3 4-(1,1,1,3,3,3-F.sub.6-propan-2-yl)Ph Me H 0 m.p.: 194-196° C. 1-91 SO.sub.2Et 4-CF.sub.3 4-CF.sub.3CH.sub.2—Ph Me H 0 m.p.: 154-156° C. 1-92 SO.sub.2Et 4-CF.sub.3 6-OCF.sub.3-pyridine-3-yl Me H 0 viscous oil 1-93 SO.sub.2Et 4-CF.sub.3 4-I—Ph Me H 0 m.p.: 233-235° C. 1-94 SO.sub.2Et 4-CF.sub.3 4-OCH.sub.2OMe—Ph Me H 0 m.p.: 129-130° C. 1-95 SO.sub.2Et 4-CF.sub.3 4-OSO.sub.2CF.sub.3—Ph Me H 0 m.p.: 155-156° C. 1-96 SO.sub.2Et 4-CF.sub.3 4-OCH.sub.2CF.sub.3—Ph Me H 0 m.p.: 159-160° C. 1-97 SO.sub.2Et 4-CF.sub.3 4-SF.sub.5—Ph Me H 0 m.p.: 160-163° C. 1-98 SO.sub.2Et 4-CF.sub.3 3-Cl-4-CF.sub.3—Ph Me H 0 m.p.: 124-126° C. 1-99 SO.sub.2Et 4-CF.sub.3 6-C.sub.2F.sub.5-pyridine-3-yl Me H 0 amorphous 1-100 SO.sub.2Et 4-CF.sub.3 4-CN—Ph Me H 0 m.p.: 184-188° C. 1-101 SO.sub.2Et 4-CF.sub.3 3-F-4-CF.sub.3—Ph Me H 0 m.p.: 85-88° C. 1-102 SO.sub.2Et 4-CF.sub.3 3-CN-4-CF.sub.3—Ph Me H 0 m.p.: 171-173° C. 1-103 OCH.sub.2OMe 4-CF.sub.3 4-CF.sub.3—Ph Me H 0 m.p.: 102-103° C. 1-104 OH 4-CF.sub.3 4-CF.sub.3—Ph Me H 0 m.p.: 217-221° C. 1-105 OCH.sub.2SMe 4-CF.sub.3 4-CF.sub.3—Ph Me H 0 m.p.: 136-138° C. 1-106 OCH.sub.2SOMe 4-CF.sub.3 4-CF.sub.3—Ph Me H 0 m.p.: 160-163° C. 1-107 OCH.sub.2SO.sub.2Me 4-CF.sub.3 4-CF.sub.3—Ph Me H 0 viscous oil 1-108 OCH.sub.2CF.sub.3 4-CF.sub.3 4-CF.sub.3—Ph Me H 0 n.sub.D(18.6° C.)1.5098 1-109 OSO.sub.2Me 4-CF.sub.3 4-CF.sub.3—Ph Me H 0 n.sub.D(19.4° C.)1.5360 1-110 SO.sub.2Et 4-CF.sub.3 6-CF.sub.3-pyridazin-3-yl Me H 0 m.p.: 222-224° C. 1-111 SO.sub.2Et 4-CF.sub.3 2-F-4-OCF.sub.3—Ph Me H 0 m.p.: 116-119° C. 1-112 SEt 4-CF.sub.3 4-OCF.sub.3—Ph Me H 0 m.p.: 115-116° C. 1-113 SOEt 4-CF.sub.3 4-OCF.sub.3—Ph Me H 0 m.p.: 153-155° C. 1-114 SO.sub.2Et 4-CF.sub.3 3-CF.sub.3-4-Cl—Ph Me H 0 m.p.: 104-109° C. 1-115 SO.sub.2Et 4-CF.sub.3 3-CF.sub.3-4-Cl—Ph Me 3-CF.sub.3-4- 0 m.p.: 206-209° C. Cl—Ph 1-116 SO.sub.2Et 4-CF.sub.3 4-(4-CF.sub.3—Ph)Ph Me H 0 m.p.: 224-226° C. 1-117 SO.sub.2Et 4-CF.sub.3 thiophen-2-yl Me I 0 m.p.: 233-234° C. 1-118 SO.sub.2Et 4-CF.sub.3 thiophen-2-yl Me H 0 m.p.: 178-179° C. 1-119 SO.sub.2Et 4-CF.sub.3 4-SC.sub.2F.sub.5—Ph Me H 0 m.p.: 93-95° C. 1-120 SO.sub.2Et 4-CF.sub.3 6-((4-OMe—Ph)CH.sub.2O)- Me H 0 amorphous pyridine-3-yl 1-121 SO.sub.2Et 4-CF.sub.3 6-Br-pyridine-3-yl Me H 0 m.p.: 198-201° C. 1-122 SO.sub.2Et 4-CF.sub.3 7-F-quinolin-3-yl Me H 0 m.p.: 196-200° C. 1-123 SO.sub.2Et 4-CF.sub.3 4-OCF.sub.2CHF.sub.2—Ph Me H 0 m.p.: 138-141° C. 1-124 SO.sub.2Et 4-CF.sub.3 2,6-Cl.sub.2-4-CF.sub.3 Me H 0 m.p.: 180-182° C. 1-125 SO.sub.2Et 4-CF.sub.3 2,6-Me.sub.2-4- Me H 0 viscous oil (perfluoropropan- 2-yl)Ph

[0406] TABLE 2 shows the substituens of the compound represented by formula (2).

##STR00016##

TABLE-US-00002 TABLE 2 Physical No. R.sup.1 (X.sup.1)n1 Ar R.sup.2 R.sup.3 m Property 2-1 SO.sub.2Et 5-CF.sub.3 4-CF.sub.3—Ph Me H 0 m.p.: 97-101° C. 2-2 SEt 5-CF.sub.3 4-CF.sub.3—Ph Me H 0 m.p.: 151-153° C. 2-3 F — 4-CF.sub.3—Ph Me H 0 m.p.: 213-214° C. 2-4 SEt — 4-CF.sub.3—Ph Me H 0 m.p.: 145-147° C. 2-5 SO.sub.2Et — 4-CF.sub.3—Ph Me H 0 m.p.: 133-136° C. 2-6 SO.sub.2Et — 4-OCF.sub.3—Ph Me H 0 n.sub.D(22.1° C.)1.5629 2-7 SO.sub.2Et — 6-CF.sub.3- Me H 0 m.p.: 157-163° C. pyridine- 3-yl 2-8 SO.sub.2Et — 4-C.sub.2F.sub.5—Ph Me H 0 m.p.: 145-147° C. 2-9 SO.sub.2Et — 4-SCF.sub.3—Ph Me H 0 m.p.: 135-137° C.

[0407] TABLE 3 shows the substituents of the compounds represented by formula (3).

##STR00017##

TABLE-US-00003 TABLE 3 Physical No. R.sup.1 (X.sup.1)n1 Ar R.sup.2 R.sup.3 m Property 3-1 SO.sub.2Et — 4-CF.sub.3—Ph Me H 0 nD(21.0° C.)1.5452 3-2 SEt — 4-CF.sub.3—Ph Me H 0 nD(21.4° C.)1.6008 3-3 F — 4-CF.sub.3—Ph Me H 1 m.p. 189-193° C. 3-4 F — 4-CF.sub.3—Ph Me H 0 m.p. 153-155° C.

[0408] TABLE 4 shows the substitutents of the compound represented by formula (4).

##STR00018##

TABLE-US-00004 TABLE 4 Physical No. R.sup.1 (X.sup.1)n Ar R.sup.2 R.sup.3 m Property 4-1 SEt 4-CF.sub.3 4-CF.sub.3—Ph OMe H 0 m.p.: 106-109° C. 4-2 SEt 4-CF.sub.3 4-CF.sub.3—Ph OH H 0 m.p.: 245-249° C. 4-3 SO.sub.2Et 4-CF.sub.3 4-CF.sub.3—Ph Me Me 0 m.p.: 195-197° C. 4-4 SEt 4-CF.sub.3 4-CF.sub.3—Ph Me Me 0 m.p.: 147-149° C. 4-5 SEt 4-CF.sub.3 4-CF.sub.3—Ph Me Br 0 m.p.: 153-155° C. 4-6 SEt 4-CF.sub.3 4-CF.sub.3—Ph Me H 0 m.p.: 109-111° C. 4-7 F 4-CF.sub.3 4-CF.sub.3—Ph Me H 0 m.p.: 73-75° C. 4-8 SO.sub.2Et 4-CF.sub.3 4-CF.sub.3—Ph Me H 0 m.p.: 180-181° C. 4-9 SOEt 4-CF.sub.3 4-CF.sub.3—Ph Me H 0 m.p.: 138-139° C.

[0409] TABLE 5 shows the substituents of the compounds represented by formula (5).

##STR00019##

TABLE-US-00005 TABLE 5 Physical No. R.sup.1 (X.sup.1)n1 Ar R.sup.2 R.sup.3 m Property 5-1 SEt — 4-CF.sub.3—Ph Me H 0 m.p. 79-84° C.

[0410] TABLE 6 shows the substituents of the compounds repreented by formula (6).

##STR00020##

TABLE-US-00006 TABLE 6 No. R.sup.1 (X.sup.1)n1 Ar R.sup.2 R.sup.3 m Physical Property 6-1 SO.sub.2Et 4-CF.sub.3 4-CF.sub.3—Ph Me H 0 n.sub.D(22.0° C.)1.529 6-2 F 4-CF.sub.3 4-CF.sub.3—Ph Me H 0 m.p.: 144-145° C. 6-3 SEt 4-CF.sub.3 4-CF.sub.3—Ph Me H 0 m.p.: 118-121° C. 6-4 SO.sub.2Et 4-CF.sub.3 2-F-4-CF.sub.3—Ph Me H 0 m.p.: 140-141° C. 6-5 SEt 4-CF.sub.3 4-OCF.sub.3—Ph Me H 0 m.p.: 92-94° C. 6-6 SO.sub.2Et 4-CF.sub.3 4-OCF.sub.3—Ph Me H 0 viscous oil 6-7 SO.sub.2Et 4-CF.sub.3 4-OCF.sub.3—Ph Me Cl 0 m.p.: 140-142° C. 6-8 SEt 4-CF.sub.3 6-CF.sub.3-pyridine-3-yl Me H 0 m.p.: 138-139° C. 6-9 SOEt 4-CF.sub.3 6-CF.sub.3-pyridine-3-yl Me H 0 m.p.: 170-172° C. 6-10 SO.sub.2Et 4-CF.sub.3 6-CF.sub.3-pyridine-3-yl Me H 0 n.sub.D(20.1° C.)1.5334 6-11 SO.sub.2Et 4-CF.sub.3 4-C.sub.2F.sub.5—Ph Me H 0 n.sub.D(18.3° C.)1.5183 6-12 SO.sub.2Et 4-OCF.sub.3 4-CF.sub.3—Ph Me H 0 viscous oil 6-13 SO.sub.2Et 4-SO.sub.2Et 4-CF.sub.3—Ph Me H 0 viscous oil 6-14 SO.sub.2Et 4-Cl 4-CF.sub.3—Ph Me H 0 viscous oil 6-15 S.sup.iPr 4-CF.sub.3 4-CF.sub.3—Ph Me H 0 m.p.: 114-116° C. 6-16 SO.sub.2.sup.iPr 4-CF.sub.3 4-CF.sub.3—Ph Me H 0 n.sub.D(20.0° C.)1.5258 6-17 SO.sub.2Et 4-CN 4-CF.sub.3—Ph Me H 0 m.p.: 192-193° C. 6-18 SO.sub.2Et 4-CF.sub.3 4-SCF.sub.3—Ph Me H 0 viscous oil 6-19 SO.sub.2Et 4-CF.sub.3 2-CF.sub.3-thiazol-5-yl Me H 0 viscous oil 6-20 F 4-CO.sub.2Me 4-CF.sub.3—Ph Me H 0 m.p.: 188-189° C. 6-21 SEt 4-CONMe.sub.2 4-CF.sub.3—Ph Me H 0 m.p.: 116-117° C. 6-22 SO.sub.2Et 4-CONMe.sub.2 4-CF.sub.3—Ph Me H 0 m.p.: 170-173° C. 6-23 SO.sub.2Et 4-Me 4-CF.sub.3—Ph Me H 0 m.p.: 172-175° C. 6-24 SO.sub.2Et 4-CO.sub.2Me 4-CF.sub.3—Ph Me H 0 amorphous 6-25 SO.sub.2Et 4-CO.sub.2.sup.tBu 4-CF.sub.3—Ph Me H 0 viscous oil 6-26 SO.sub.2Et 4-CH.sub.2OH 4-CF.sub.3—Ph Me H 0 m.p.: 184-188° C. 6-27 SO.sub.2Et 4-CHO 4-CF.sub.3—Ph Me H 0 amorphous 6-28 SO.sub.2Et 4-CHF.sub.2 4-CF.sub.3—Ph Me H 0 amorphous 6-29 SO.sub.2Et 4-CF.sub.3 4-CF.sub.3—Ph Me Cl 0 amorphous 6-30 SO.sub.2Et 4-CF.sub.3 4-CF.sub.3—Ph Me H 0 m.p.: 110-115° C. 6-31 SO.sub.2Et 4-CF.sub.3 4-CF.sub.3—Ph Me Br 0 m.p.: 210-212° C. 6-32 SO.sub.2Et 4-CF.sub.3 4-CF.sub.3—Ph Me Me 0 m.p.: 157-160° C. 6-33 Cl 2-Cl-4-CF.sub.3 4-CF.sub.3—Ph Me H 0 m.p.: 139-141° C. 6-34 SEt 2-Cl-4-CF.sub.3 4-CF.sub.3—Ph Me H 0 viscous oil 6-35 SO.sub.2Et 2-Cl-4-CF.sub.3 4-CF.sub.3—Ph Me H 0 viscous oil 6-36 SO.sub.2Et 4-CF.sub.3 5-CF.sub.3-thiophen-2-yl Me H 0 m.p.: 158-159° C. 6-37 CN 4-CF.sub.3 4-CF.sub.3—Ph Me H 0 m.p.: 175-179° C. 6-38 CONMe.sub.2 4-CF.sub.3 4-CF.sub.3—Ph Me H 0 n.sub.D(22.1° C.)1.5407 6-39 CONHMe 4-CF.sub.3 4-CF.sub.3—Ph Me H 0 m.p.: 190-193° C. 6-40 SEt 4-CF.sub.3 3-CF.sub.3—Ph Me H 0 m.p.: 127-129° C. 6-41 SO.sub.2Et 4-CF.sub.3 3-CF.sub.3—Ph Me H 0 m.p.: 86-88° C. 6-42 SMe 4-CF.sub.3 4-CF.sub.3—Ph Me H 0 m.p.: 115-117° C. 6-43 SOMe 4-CF.sub.3 4-CF.sub.3—Ph Me H 0 m.p.: 157-159° C. 6-44 SO.sub.2Me 4-CF.sub.3 4-CF.sub.3—Ph Me H 0 viscous oil 6-45 SCH.sub.2CF.sub.3 4-CF.sub.3 4-CF.sub.3—Ph Me H 0 m.p.: 107-110° C. 6-46 SO.sub.2CH.sub.2CF.sub.3 4-CF.sub.3 4-CF.sub.3—Ph Me H 0 m.p.: 142-143° C. 6-47 N═S(═O)Me.sub.2 4-CF.sub.3 4-CF.sub.3—Ph Me H 0 m.p.: 154-156° C. 6-48 CONH.sup.sBu 4-CF.sub.3 4-CF.sub.3—Ph Me H 0 m.p.: 85-87° C. 6-49 CON(Me).sup.sBu 4-CF.sub.3 4-CF.sub.3—Ph Me H 0 n.sub.D(21.8° C.)1.5288 6-50 SEt 4-CF.sub.3 4-SF.sub.5—Ph Me H 0 m.p.: 103-105° C. 6-51 SO.sub.2Et 4-CF.sub.3 4-SF.sub.5—Ph Me H 0 n.sub.D(22.8° C.)1.5238 6-52 SEt 4-CF.sub.3 4-Cl—Ph Me H 0 m.p.: 112-114° C. 6-53 SO.sub.2Et 4-CF.sub.3 4-Cl—Ph Me H 0 amorphous 6-54 SEt 4-CF.sub.3 3-Cl-4-CF.sub.3—Ph Me H 0 viscous oil 6-55 SO.sub.2Et 4-CF.sub.3 3-Cl-4-CF.sub.3—Ph Me H 0 amorphous 6-56 SO.sub.2Et 4-CF.sub.3 4-C.sub.2F.sub.5—Ph Me H 0 amorphous 6-57 SEt 4-CF.sub.3 2,2-F.sub.2-benzo[1,3]dioxol- Me H 0 n.sub.D(23.2° C.)1.5659 5-yl 6-58 SO.sub.2Et 4-CF.sub.3 2,2-F.sub.2-benzo[1,3]dioxol- Me H 0 m.p.: 140-144° C. 5-yl 6-59 S.sup.nPr 4-CF.sub.3 4-CF.sub.3—Ph Me H 0 m.p.: 104-106° C. 6-60 SO.sub.2.sup.nPr 4-CF.sub.3 4-CF.sub.3—Ph Me H 0 m.p.: 126-130° C. 6-61 S(═O)(═N—CN)Et 4-CF.sub.3 4-CF.sub.3—Ph Me H 0 amorphous 6-62 F 4-CF.sub.3 5-CF.sub.3-pyridine-2-yl Me H 0 m.p.: 111-113° C. 6-63 SEt 4-CF.sub.3 5-CF.sub.3-pyridine-2-yl Me H 0 m.p.: 105-107° C. 6-64 SO.sub.2Et 4-CF.sub.3 5-CF.sub.3-pyridine-2-yl Me H 0 amorphous 6-65 S(═O)(═N—COCF.sub.3)Et 4-CF.sub.3 4-CF.sub.3—Ph Me H 0 viscous oil 6-66 S(═O)(═NH)Et 4-CF.sub.3 4-CF.sub.3—Ph Me H 0 m.p.: 138-140° C. 6-67 S(═O)(═NMe)Et 4-CF.sub.3 4-CF.sub.3—Ph Me H 0 m.p.: 168-169° C. 6-68 SEt 4-CF.sub.3 3,5-(CF.sub.3).sub.2—Ph Me 3,5-(CF.sub.3).sub.2—Ph 0 viscous oil 6-69 SO.sub.2Et 4-CF.sub.3 3,5-(CF.sub.3).sub.2—Ph Me H 0 viscous oil 6-70 SEt 4-CF.sub.3 4-(perfluoropropan- Me Br 0 m.p.: 105-107° C. 2-yl)Ph 6-71 SOEt 4-CF.sub.3 4-(perfluoropropan- Me H 0 m.p.: 170-171° C. 2-yl)Ph 6-72 SEt 4-CF.sub.3 3,4-Cl.sub.2—Ph Me Br 0 m.p.: 119-120° C. 6-73 SEt 4-CF.sub.3 3,4-Cl.sub.2—Ph Me H 0 viscous oil 6-74 SO.sub.2Et 4-CF.sub.3 3,4-Cl.sub.2—Ph Me H 0 m.p.: 125-126° C. 6-75 F 4-CF.sub.3 4-CN—Ph Me H 0 m.p.: 177-178° C. 6-76 SEt 4-CF.sub.3 6-C.sub.2F.sub.5-pyridine-3-yl Me Br 0 viscous oil 6-77 SEt 4-CF.sub.3 4-CN—Ph Me H 0 m.p.: 130-132° C. 6-78 F 4-CF.sub.3 3-SEt-4-CF.sub.3—Ph Me H 0 m.p.: 160-163° C. 6-79 F 4-CF.sub.3 3-SOEt-4-CF.sub.3—Ph Me H 0 m.p.: 130-133° C. 6-80 F 4-CF.sub.3 3-SO.sub.2Et-4-CF.sub.3—Ph Me H 0 m.p.: 141-143° C. 6-81 SEt 4-CF.sub.3 3-SEt-4-CF.sub.3—Ph Me H 0 m.p.: 89-90° C. 6-82 SO.sub.2Et 4-CF.sub.3 3-SOEt-4-CF.sub.3—Ph Me H 0 m.p.: 90-94° C. 6-83 SO.sub.2Et 4-CF.sub.3 3-SO.sub.2Et-4-CF.sub.3—Ph Me H 0 m.p.: 177-180° C. 6-84 F 4-CF.sub.3 3-NO.sub.2-4-CF.sub.3—Ph Me H 0 m.p.: 99-102° C. 6-85 CH.sub.2CONHMe 4-CF.sub.3 4-CF.sub.3—Ph Me H 0 m.p.: 150-152° C. 6-86 CH.sub.2CONMe.sub.2 4-CF.sub.3 4-CF.sub.3—Ph Me H 0 viscous oil 6-87 F 4-CF.sub.3 3-NH.sub.2-4-CF.sub.3—Ph Me H 0 m.p.: 158-159° C. 6-88 SEt 4-CF.sub.3 3-NH.sub.2-4-CF.sub.3—Ph Me H 0 m.p.: 130-132° C. 6-89 SO.sub.2Et 4-CF.sub.3 3-NH.sub.2-4-CF.sub.3—Ph Me H 0 m.p.: 200-202° C. 6-90 SEt 4-CF.sub.3 3-Br-4-CF.sub.3—Ph Me H 0 m.p.: 116-118° C. 6-91 SO.sub.2Et 4-CF.sub.3 3-Br-4-CF.sub.3—Ph Me H 0 amorphous 6-92 SEt 4-CF.sub.3 4-.sup.nBt-6-C.sub.2F.sub.5- Me H 0 m.p.: 110-112° C. pyridine-3-yl 6-93 SEt 4-CF.sub.3 3-Cl-4-OCF.sub.3—Ph Me Br 0 m.p.: 104-105° C. 6-94 SEt 4-CF.sub.3 3-Cl-4-OCF.sub.3—Ph Me H 0 viscous oil 6-95 SOEt 4-CF.sub.3 3-Cl-4-OCF.sub.3—Ph Me H 0 amorphous 6-96 SEt 4-CF.sub.3 2-Cl-4-CF.sub.3—Ph Me Br 0 m.p.: 128-129° C. 6-97 SO.sub.2Et 4-CF.sub.3 4-CN—Ph Me H 0 m.p.: 183-185° C. 6-98 SO.sub.2Et 4-CF.sub.3 4-CHO Me H 0 m.p.: 147-148° C.

[0411] TABLE 7 shows the substituents of the compounds represented by formula (7).

##STR00021##

TABLE-US-00007 TABLE 7 No. R.sup.1 (X.sup.1)n1 Ar R.sup.2 R.sup.3 m Physical Property 7-1 SEt 5-CF.sub.3 4-CF.sub.3—Ph Me H 0 m.p. 123-125° C. 7-2 SO.sub.2Et 5-CF.sub.3 4-CF.sub.3—Ph Me H 0 m.p. 172-173° C.

[0412] TABLE 8 shows the substituents of the compounds represented by formula (8).

##STR00022##

TABLE-US-00008 TABLE 8 No. R.sup.1 (X.sup.1)n1 Ar R.sup.2 R.sup.3 m Physical Property 8-1 SEt 6-CF.sub.3 4-CF.sub.3—Ph Me H 0 viscous oil 8-2 SO.sub.2Et 6-CF.sub.3 4-CF.sub.3—Ph Me H 0 m.p. 216-218° C.

[0413] TABLE 9 shows the substituents of the compounds represented by fon lulu (9).

##STR00023##

TABLE-US-00009 TABLE 9 No. R.sup.1 (X.sup.1)n1 Ar R.sup.2 R.sup.3 m Physical Property 9-1 F 4-CF.sub.3 4-CF.sub.3—Ph Me H 0 m.p.: 153-154° C. 9-2 SEt 4-CF.sub.3 4-CF.sub.3—Ph Me H 0 m.p.: 93-94° C. 9-3 SO.sub.2Et 4-CF.sub.3 4-CF.sub.3—Ph Me H 0 m.p.: 138-140° C.

[0414] TABLE 10 shows .sup.1H-NMR data measured for some pompounds selected from TABLE 1 to TABLE 9. The measuring temperature is 23° C. (*: measuring temperature of 140° C.).

TABLE-US-00010 TABLE 10 Compound No. NMR   (δ ppm) 1-2  .sup.1H-NMR (400 MHz, CDCl.sub.3): 8.88 (m, 1H), 7.94 (m, 1H), 7.77 (d, 1H), 7.71 (s, 1H), 7.61 (s, 1H), 7.52 (m, 1H), 3.86 (s, 3H), 2.94 (q, 2H), 1.30 (t 3H). 1-9  .sup.1H-NMR (400 MHz, CDCl.sub.3): d 7.84 (d, 1H), 7.67-7.50 (m, 6H), 7.46 (d, 1H), 7.18 (s, 1H), 3.21 (s, 3H), 2.88 (q, 2H), 1.29 (t, 3H). 1-10 .sup.1H-NMR (400 MHz, CDCl.sub.3): d 7.78 (d, 2H), 7.61-7.50 (m, 5H), 7.43 (s, 1H), 7.40 (m, 1H), 3.47 (s, 1H), 3.00-2.88 (m, 1H), 1.29 (t, 3H). 1-23 .sup.1H-NMR (400 MHz, CDCl.sub.3): d 7.73 (d, 2H), 7.61-7.59 (m, 3H), 7.54-7.50 (m, 2H), 7.28 (s, 1H), 3.94 (q, 2H), 2.65 (q, 2H), 1.32 (t, 3H), 0.97 (t, 3H). 1-33 .sup.1H-NMR (400 MHz, CDCl.sub.3): d 7.73 (d, 2H), 7.68-7.66 (m, 2H), 7.60 (d, 2H), 7.46 (d, 1H), 7.33 (s, 1H), 3.52 (s, 3H), 2.97 (q, 2H), 1.34 (t, 3H). 1-34 H-NMR (400 MHz, CDCl.sub.3): d 8.34 (d, 1H), 7.99 (dd, 1H), 7.85 (d, 1H), 7.74 (d, 2H), 7.60 (d, 2H), 7.26 (s, 1H), 3.48-3.42 (m, 5H), 1.26 (m, 3H). 1-51 .sup.1H-NMR (400 MHz, CDCl.sub.3): d 8.48 (d, 1H), 8.01 (dd, 1H), 7.80 (d, 1H), 7.71 (m, 4H), 7.23 (s, 1H), 3.70 (q, 2H), 3.40 (m, 1H), 1.31 (t, 3H), 0.64 (m, 4H). 1-61 .sup.1H-NMR (400 MHz, CDCl.sub.3): d 7.72 (d, 2H), 7.61-7.60 (m, 3H), 7.57-7.55 (m, 2H), 7.36 (s, 1H), 3.39 (s, 3H), 2.98-2.88 (m, 2H), 1.30 (t, 3H). 1-62 .sup.1H-NMR (400 MHz, CDCl.sub.3): d 8.43 (d, 1H), 8.13 (d, 1H), 7.89 (t, 1H), 7.72 (d, 2H), 7.60 (d, 2H), 7.30 (s, 1H), 3.48-3.22 (m, 2H), 3.37 (s, 3H), 1.21 (t, 3H). 1-63 .sup.1H-NMR (400 MHz, CDCl.sub.3): d 8.30 (d, 1H), 7.98 (m, 1H), 7.91 (t, 1H), 7.75 (d, 2H), 7.59 (d, 2H), 7.27 (s, 1H), 3.41 (s, 3H), 3.23-2.82 (m, 2H), 1.26 (t, 3H). 1-87 .sup.1H-NMR (400 MHz, CDCl.sub.3): d 8.52 (d, 1H), 8.04 (dd, 1H), 7.75-7.73 (m, 3H), 7.60 (d, 2H), 7.28 (s, 1H), 3.44 (s, 3H), 3.30 (s, 3H). 1-92 .sup.1H-NMR (400 MHz, CDCl.sub.3): d 8.46-8.45 (m, 2H), 8.04 (m, 1H), 7.90 (m, 1H), 7.73 (d, 1H), 7.14 (d, 1H), 3.46 (q, 2H), 3.42 (s, 3H), 1.26 (t, 3H). 1-99 .sup.1H-NMR (400 MHz, CDCl.sub.3): d 8.90 (d, 1H), 8.47 (d, 1H), 8.05 (dd, 1H), 8.00 (dd, 1H), 7.83 (d, 1H), 7.75 (d, 1H), 3.48 (s, 3H), 3.46 (q, 2H), 1.27 (t, 3H).  1-107 .sup.1H-NMR (400 MHz, CDCl.sub.3): d 7.76-7.74 (m, 3H), 7.64-7.61 (m, 2H), 7.56 (d, 1H), 7.34 (m, 1H), 7.31 (s, 1H), 4.96 (s, 2H), 3.59 (s, 3H), 2.76 (s, 3H). Compound No. NMR   (δ ppm)  1-120 .sup.1H-NMR (400 MHz, CDCl.sub.3): d 8.44 (d, 1H), 8.00 (dd, 1H), 7.66 (d, 1H), 7.40-7.36 (m, 2H), 7.32 (m, 2H), 7.05 (s, 1H), 6.90 (m, 2H), 6.69 (d, 1H), 5.13 (s, 2H), 3.80 (s, 3H), 3.43 (q, 2H), 3.27 (s, 3H), 1.24 (t, 3H).  1-125 .sup.1H-NMR (400 MHz, CDCl.sub.3): d 8.47 (d, 1H), 8.02 (dd, 1H), 7.73 (d, 1H), 7.39 (s, 2H), 7.03 (s, 1H), 3.47 (q, 2H), 3.09 (s, 3H), 1.26 (t, 3H). 6-6 .sup.1H-NMR (400 MHz, CDCl.sub.3): d 8.51 (d, 1H), 8.01 (dd, 1H), 7.76-7.73 (m, 2H), 7.67 (d, 2H), 7.35 (m, 1H), 7.15 (s, 1H), 3.48 (s, 3H), 3.07 (q, 2H), 1.20 (t, 3H). 6-12 .sup.1H-NMR (400 MHz, CDCl.sub.3): d 8.10 (d, 1H), 7.84 (d, 2H), 7.75 (d, 2H), 7.58 (m, 2H), 7.14 (s, 1H), 3.50 (s, 3H), 3.07 (q, 2H), 1.20 (t, 3H). 6-13 .sup.1H-NMR (400 MHz, CDCl.sub.3): d 8.74 (d, 1H), 8.29 (dd, 1H), 7.85 (d, 2H), 7.78-7.73 (m, 3H), 7.20 (s, 1H), 3.51 (s, 3H), 3.26 (q, 2H), 3.08 (q, 2H), 1.39 (t, 3H), 1.22 (t, 3H). 6-14 .sup.1H-NMR (400 MHz, CDCl.sub.3): d 8.23 (d, 1H), 8.84 (d, 2H), 7.75 (d, 2H), 7.72 (dd, 1H), 7.45 (d, 1H), 7.36 (s, 1H), 7.13 (s, 1H), 3.48 (s, 3H), 3.05 (q, 2H), 1.20 (t, 3H). 6-18 .sup.1H-NMR (400 MHz, CDCl.sub.3): d 8.49 (m, 1H), 8.00 (m, 1H), 7.75 (m, 4H), 7.64 (m, 1H), 7.15 (s, 1H), 3.49 (s, 3H), 3.05 (q, 2H), 1.19 (t, 3H). 6-19 .sup.1H-NMR (400 MHz, CDCl.sub.3): d 8.50 (d, 1H), 8.19 (d, 2H), 8.03 (dd, 1H), 7.65 (d, 1H), 7.17 (s, 1H), 7.13 (s, 1H), 3.61 (s, 3H), 3.05 (q, 2H), 1.22 (t, 3H). 6-24 .sup.1H-NMR (400 MHz, CDCl.sub.3): d 8.86 (d, 1H), 8.40 (dd, 1H), 7.85 (d, 2H), 7.75 (d, 2H), 7.61 (d, 1H), 7.27 (s, 1H), 4.02 (s, 3H), 3.49 (s, 3H), 3.07 (q, 2H), 1.20 (t, 3H). 6-25 .sup.1H-NMR (400 MHz, CDCl.sub.3): d 8.78 (d, 1H), 8.33 (dd, 1H), 7.85 (m, 2H), 7.75 (m, 2H), 7.57 (d, 1H), 7.16 (s, 1H), 3.48 (s, 3H), 3.06 (q, 2H), 1.65 (s, 9H), 1.20 (t, 3H). 6-27 .sup.1H-NMR (400 MHz, CDCl.sub.3): d 10.20 (s, 1H), 8.72 (d, 1H), 8.26 (dd, 1H), 7.85 (m, 2H), 7.76 (m, 2H), 7.70 (d, 1H), 7.19 (s, 1H), 3.51 (s, 3H), 3.08 (q, 2H), 1.21 (t, 3H). 6-28 .sup.1H-NMR (400 MHz, CDCl.sub.3): d 8.38 (s, 1H), 7.92 (d, 1H), 7.85 (d, 2H), 7.76 (d, 2H), 7.63 (d, 1H), 7.17 (s, 1H), 6.81 (t, 1H), 3.50 (s, 3H), 3.07 (q, 2H), 1.20 (t, 3H). 6-29 .sup.1H-NMR (400 MHz, CDCl.sub.3): d 8.52 (d, 1H), 8.06 (dd, 1H), 7.84 (m, 2H), 7.76 (m, 2H), 7.68 (d, 1H), 3.50 (s, 3H), 3.10 (q, 2H), 1.23 (t, 3H). 6-34 .sup.1H-NMR (400 MHz, CDCl.sub.3): d 7.88 (d, 2H), 7.75 (d, 2H), 7.54 (s, 1H), 7.38 (s, 1H), 7.19 (s, 1H), 3.50 (s, 3H), 2.95 (q, 2H), 1.35 (t, 3H). 6-35 .sup.1H-NMR (400 MHz, CDCl.sub.3): d 8.42 (d, 1H), 8.09 (d, 1H), 7.86 (d, 2H), 7.77 (d, 2H), 7.16 (s, 1H), 3.50 (s, 3H), 3.19 (q, 2H), 1.28 (t, 3H). 6-44 .sup.1H-NMR (400 MHz, CDCl.sub.3): d 8.58 (d, 1H), 8.02 (dd, 1H), 7.85 (d, 2H), 7.76 (d, 2H), 7.68 (d, 1H), 7.22 (s, 1H), 3.50 (s, 3H), 3.02 (q, 2H). Compound No. NMR   (δ ppm) 6-53 .sup.1H-NMR (400 MHz, CDCl.sub.3): d 8.50 (m, 1H), 7.99 (m, 1H), 7.67-7.64 (m, 3H), 7.48 (d, 1H), 7.14 (s, 1H), 3.46 (s, 3H), 3.07 (q, 2H), 1.20 (t, 3H). 6-54 .sup.1H-NMR (400 MHz, CDCl.sub.3): d 7.93 (s, 1H), 7.81 (d, 1H), 7.74 (m, 1H), 7.56 (s, 1H), 7.48 (m, 1H), 7.40 (d, 1H), 7.21 (s, 1H), 3.57 (s, 3H), 2.96 (t, 2H), 1.34 (t, 3H). 6-55 .sup.1H-NMR (400 MHz, CDCl.sub.3): d 8.51 (m, 1H), 8.01 (m, 1H), 7.91 (s, 1H), 7.81 (d, 1H), 7.71 (m, 1H), 7.66 (d, 1H), 7.18 (s, 1H), 3.51 (s, 3H), 3.07 (q, 2H), 1.21 (t, 3H). 6-56 .sup.1H-NMR (400 MHz, CDCl.sub.3): d 8.51 (m, 1H), 8.01 (m, 1H), 7.78 (m, 4H), 7.66 (d, 1H), 7.17 (s, 1H), 3.51 (s, 3H), 3.07 (q, 2H), 1.21 (t, 3H). 6-61 .sup.1H-NMR (400 MHz, CDCl.sub.3): d 8.53 (br s, 1H), 8.13 (dd, 1H), 7.86-7.76 (m, 5H), 7.12 (s, 1H), 3.56 (br s, 3H), 3.45 (m, 2H), 3.07 (q, 2H), 1.38 (br t, 3H). 6-64 .sup.1H-NMR (400 MHz, CDCl.sub.3): d 8.88 (m, 1H), 8.51 (m, 1H), 8.39 (d, 1H), 8.02 (m, 2H), 7.65 (d, 1H), 7.21 (s, 1H), 3.89 (s, 3H), 3.08 (q, 2H), 1.22 (t, 3H). 6-65 .sup.1H-NMR (400 MHz, DMSO-d6)*: d 8.38 (s, 1H), 8.27 (d, 1H), 7.96-7.83 (m, 5H), 7.33 (s, 1H), 3.80 (m, 2H), 3.48 (s, 3H), 1.28 (t, 3H). 6-68 .sup.1H-NMR (400 MHz, CDCl.sub.3): d 8.26 (s, 2H), 8.00 (s, 1H), 7.90 (s, 2H), 7.65 (d, 2H), 7.54 (m, 1H), 7.41 (d, 1H), 3.54 (s, 3H), 3.07-2.93 (m, 2H), 1.32 (t, 3H). 6-69 .sup.1H-NMR (400 MHz, CDCl.sub.3): d 8.51 (d, 1H), 8.19 (s, 2H), 8.02 (dd, 1H), 7.96 (s, 1H), 7.67 (d, 1H), 7.20 (s, 1H), 3.53 (s, 3H), 3.09 (q, 2H), 1.23 (t, 3H). 6-73 .sup.1H-NMR (400 MHz, CDCl.sub.3): d 7.85 (d, 1H), 7.57-7.55 (m, 3H), 7.48 (dd, 1H), 7.39 (d, 1H), 7.18 (s, 1H), 3.53 (s, 3H), 2.95 (q, 2H), 1.34 (t, 3H). 6-76 .sup.1H-NMR (400 MHz, CDCl.sub.3): d 9.09 (d, 1H), 8.32 (dd, 1H), 7.85 (dd, 1H), 7.62 (s, 1H), 7.55 (dd, 1H), 7.45 (d, 1H), 3.59 (s, 3H), 2.97 (q, 2H), 1.33 (t, 3H). 6-86 .sup.1H-NMR (400 MHz, CDCl.sub.3): d 7.83 (d, 2H), 7.75 (d, 2H), 7.65-7.63 (m, 2H), 7.12 (s, 1H), 3.75 (s, 2H), 3.53 (s, 3H), 2.94 (s, 3H), 2.87 (s, 3H). 6-91 .sup.1H-NMR (400 MHz, CDCl.sub.3): d 8.51 (s, 1H), 8.12 (s, 1H), 8.01 (d, 1H), 7.81 (d, 1H), 7.76 (d, 1H), 7.66 (d, 1H), 7.20 (s, 1H), 3.51 (s, 3H), 3.07 (q, 2H), 1.21 (t, 3H). 6-94 .sup.1H-NMR (400 MHz, CDCl.sub.3): d 7.88 (d, 1H), 7.67 (dd, 1H), 7.53 (s, 1H), 7.49-7.39 (m, 3H), 7.18 (s, 1H), 3.54 (s, 3H), 2.95 (q, 2H), 1.34 (t, 3H). 6-97 .sup.1H-NMR (400 MHz, CDCl.sub.3): d 8.51 (d, 1H), 8.01 (dd, 1H), 7.84 (d, 1H), 7.67-7.63 (m, 2H), 7.45 (m, 1H), 7.15 (s, 1H), 3.49 (s, 3H), 3.07 (q, 2H), 1.21 (t, 3H). 8-1  .sup.1H-NMR (400 MHz, CDCl.sub.3): d 7.86 (d, 2H), 7.76 (d, 2H), 7.63 (d, 1H), 7.45 (d, 1H), 7.26 (s, 1H), 3.58 (s, 3H), 3.23 (q, 2H), 1.37 (t, 3H).

[Biological Examination]

[0415] The following test examples demonstrate that the diarylimidazole compound of the present invention (hereinafter, may be referred to as “the compound of the present invention”) is useful as an active ingredient of harmful organism control agent, especially as an active ingredient of insecticide. In addition, the term “part” is based on weight.

(Preparation of Emulsion for Test)

[0416] 5 parts of the compound of the present invention, 93.6 parts of dimethyl formamide and 1.4 parts of polyoxyethylene alkylaryl ether were mixed and dissolved to obtain emulsion (I) including 5% of active ingredient.

(Test Example 1) Efficacy Test Against Pseudaletia Separate

[0417] Emulsion (I) was dilluded with water so that the concentration of the compound of the present invention reaches 125 ppm. Maize leaves were soaked in the dillued liquid for 30 seconds. Then the maize leaves were put on Petri dishes, followed by inoculating 5 second-instar larvae of Pseudaletia separate. The Petri dishes were placed in a temperature-controlled room with a temperature of 25° C. and humidity of 60%. Mortality was investigated after 6 days were passed, and the insect mortality rate was caculated. The test was repeated twice.

[0418] Efficacy test against Pseudaletia separate was carried out for the compounds shown in TABLE 11. All of the compounds demonstrated 80% or more of insect mortality rate against Pseudaletia separate.

TABLE-US-00011 TABLE 11 Compound No. 1-1 1-2 1-3 1-7 1-11 1-14 1-15 1-17 1-18 1-19 1-20 1-23 1-24 1-32 1-33 1-34 1-35 1-36 1-38 1-39 1-42 1-46 1-47 1-48 1-52 1-54 1-56 1-57 1-58 1-60 1-62 1-63 1-64 1-65 1-66 1-67 1-69 1-71 1-74 1-75 1-76 1-77 1-78 1-79 1-81 1-82 1-83 1-84 1-85 1-86 1-87 1-88 1-89 1-90 1-91 1-92 1-93 1-97 1-98 1-99 1-100 1-101 1-102 1-110 1-111 1-112 1-113 1-114 1-119 1-121 1-122 1-123 2-1 2-2 2-4 2-5 2-6 2-7 2-8 2-9 3-2 3-1 6-1 6-3 6-4 6-7 6-10 6-11 6-12 6-13 6-14 6-18 6-19 6-24 6-28 6-31 6-32 6-35 6-36 6-37 6-41 6-43 6-51 6-52 6-53 6-54 6-55 6-56 6-57 6-58 6-63 6-64

(Test Example 2) Efficacy Test Against Spodoptera Litura

[0419] Emulstion (I) was dilluded with water so that the concentration of the compound of the present invention reaches 125 ppm. Cabbage leaves were soaked in the dillued liquid for 30 seconds. Then the cabbage leaves were put on Petri dishes, followed by inoculating 5 second-instar larvae of Spodoptera litura. The Petri dishes were placed in a temperature-controlled room with a temperature was 25° C. and humidity of 60%. Mortality was investigated after 6 days were passed, and the insect mortality rate was calculated. The test was repeated twice.

[0420] Efficacy test against Spodoptera litura was carried out for the compounds shown in TABLE 12. All of the compounds demonstrated 80% or more of insect mortality rate against Spodoptera litura.

TABLE-US-00012 TABLE 12 Compound No. 1-1 1-2 1-3 1-7 1-15 1-17 1-18 1-19 1-20 1-24 1-33 1-35 1-36 1-38 1-39 1-42 1-46 1-47 1-54 1-57 1-58 1-69 1-74 1-77 1-79 1-83 1-85 1-87 1-88 1-89 1-90 1-91 1-92 1-97 1-98 1-99 1-100 1-101 1-102 1-110 1-111 1-112 1-113 1-114 1-119 1-121 1-122 2-1 6-1 6-6 6-11 6-18 6-32 6-35 6-36 6-51 6-52 6-53 6-54 6-55 6-56 6-57 6-58 6-63 6-64
(Test Example 3) Efficacy Test against Plutella xylostella

[0421] Emulstion (I) was dilluded with water so that the concentration of the compound of the present invention reaches 125 ppm. Cabbage leaves were soaked in the dillued liquid for 30 seconds. Then the cabbage leaves were put on Petri dishes, followed by inoculating 5 second-instar larvae of Plutella xylostella. The Petri dishes were placed in a temperature-controlled room with a temperature was 25° C. and humidity of 60%. Mortality was investigated after 3 days were passed, and the insect mortality rate was calculated. The test was repeated twice.

[0422] Efficacy test against Plutella xylostella was carried out for the compounds shown in TABLE 13. All of the compounds demonstrated 80% or more of mortality rate against Plutella xylostella.

TABLE-US-00013 TABLE 13 Compound No. 1-1 1-2 1-3 1-7 1-15 1-17 1-18 1-20 1-24 1-33 1-35 1-36 1-38 1-39 1-42 1-46 1-47 1-54 1-57 1-58 1-77 1-79 1-90 2-1 2-2 2-5 3-2 3-1 6-1 6-6 6-11
(Test Example 4) Efficacy Test Against Aphis gossypii

[0423] Cucumber plants were raised in No. 3 pots and the first true leaves were inoculated with nymphs of Aphis gossypii. Emulstion (I) was dilluded with water so that the concentration of the compound of the present invention reaches 125 ppm, followed by spraying the diluted liquid on the cucumber seedlings. The cucumber seedlings were then placed in a temperature-controlled room with a temperature of 25° C. and humidity of 60%. Mortality was investigated after 4 days were passed from the spraying, and the insect mortality rate of Aphis gossypii was caculated. The test was repeated twice.

[0424] Efficacy test against Aphis gossypii was carried out for the compounds shown in TABLE 14. All of the compounds demonstrated 80% or more of mortality rate against Aphis gossypii.

TABLE-US-00014 TABLE 14 Compound No. 1-3 1-8 1-13 1-14 1-17 1-20 1-24 1-33 1-35 1-39 1-42 1-46 1-47 1-54 1-57 1-58 1-65 1-66 1-69 1-79 1-83 1-84 1-86 1-87 1-88 1-89 1-90 1-91 1-92 1-97 1-98 1-99 1-100 1-101 1-102 1-111 1-114 2-1 2-5 3-2 3-1 5-1 6-1 6-6 6-12 6-14 6-18 6-19 6-24 6-28 6-36 6-41 6-51 6-52 6-53 6-55
(Test Example 5) Efficacy Test Against Bemisia tabaci

[0425] Emulsion (I) was dilluded with water so that the concentration of the compound of the present invention reaches 125 ppm, then the diluted liquid was sprayied on young seedlings of tomato, followd by air drying. On the day of the spraying, B-type adult Bemisia tabaci were released to the seedlings so as to lay eggs. The number of parasitic larvae was calculated after 12 days were passed from the spraying. The efficacy of the compound was evaluated by the following equation of prevention rate. The test was repeated twice.

Prevention rate=[1−(Nt)/(Nc)]×100

[0426] Nt: number of parasites in spray-treatment area

[0427] Nc: number of parasites in control area

[0428] Efficacy test against Bemisia tabaci was carried out for the compounds shown in TABLE 15. All of the compounds demonstrated 80% or more of prevention rate against Bemisia tabaci.

TABLE-US-00015 TABLE 15 Compound No. 1-3  1-66 1-86 1-92 3-2 1-35 1-79 1-87 1-98 3-1 1-65 1-83 1-91 2-1  6-1
(Test Example 6) Efficacy Test against Tetranychus kanzawai

[0429] Kidney bean plants were raised in No. 3 pots and the primary leaves were inoculated with 10 adult female Tetranychus kanzawai. Emulstion (I) was dilluded with water so that the concentration of the compound of the present invention reaches 125 ppm, followed by spraying the diluted liquid on the kidney bean seedlings. The kidney bean seedlings were then placed in a temperature-controlled room with a temperature of 25° C. and humidity of 65%. Mortality of the adult Tetranychus kanzawai was investigated after 10 days were passed from the spraying, and the insect mortality rate of Tetranychus kanzawai was caculated. The test was repeated twice.

[0430] The efficacy test against Tetranychus kanzawai was carried out for the compounds shown in TABLE 16. All of the compounds demonstrated 90% or more of mortality rate against Tetranychus kanzawai.

TABLE-US-00016 TABLE 16 Compound No. 1-4 1-31 1-60  1-109 6-10 9-1 1-9 1-41 1-61 3-4 6-25  1-25 1-46  1-103 6-9 6-62
(Test Example 7) Efficacy Test Against Aphis gossypii (Root-dipping Test)

[0431] Cucumber plants reaised in No. 3 pots were pulled out from the pots, then the soil attached to the roots was washed with tap water, followed by hydrophonic-cultivating the cucumber plants by soaking the roots in tap water. The cucumber seedlings were inoculated with nymphs of Aphis gossypii. Emulsion (I) was diluted with water to obtain a diluted liquid with a concentration of 8 ppm of the compound of the present invention. The tap water was replaced with the diluted liquid, and then the hydrophonic-cultivation was continued in a temperature-controlled room with a temperature was 25° C. and humidity of 60%.

[0432] After 6 days were passed from the hydrophonic-cultivation in the diluted liquid, mortality of Aphis gossypii was investigated and the insect mortality rate was calculated. The test was repeated twise.

[0433] The efficacy test against Aphis gosspii was carried out for Compound 3-1, and the insect mortality rate of Coumpound 3-1 was 80% or more.

(Test Example 8) Efficacy Test against Musca domestica

[0434] The compound of the present invention was diluted with acetone, followed by dropping to 1 g of cube sugar so that the concentration reaches to 100 ppm. The cube sugar was placed in a plastic cup and 10 adult female Musca domestica were released therein, followed by putting the lid on the cup. The cup was kept at 25° C., the mortality was investigated after 24 hours was passed from the releasing of Musca domestica and the insect mortality rate was calculated by the following equation. The test was repeated twise.

[0435] Insect mortality rate (%)=(number of dead insects/number of sample insects)×100

[0436] The efficacy test against Musca domestica was carried out for Compound 1-35. As a result, the insect mortality rate against the adult female Musca domestica was 100%.

(Test Example 9) Efficacy Test Against Culex pipiens

[0437] Emulsion (I) was diluted with water so that the concentration of the compound of the present invention reaches 2 ppm to prepare a chemical solution for test. 20 first-instar larvae of Culex pipiens were released into 100 ml of the chemical solution for test, then the number of dead insects was calculated after 1 day was passed, and the insect mortality rate was calculated by the following equation. The test was repeated twice.

[0438] Insect mortality rate (%)=(number of dead insects/number of sample insects)×100

[0439] The efficacy test against the first-instar larvae of Culex pipiens was carried out for Compound 1-35. As a result, the insect mortality rate against the first-instar larvae of Culex pipiens was 100%.

(Test Example 10) Efficacy Test Against Plutella xylostella (Soil Irrigating Test)

[0440] Emulsion (I) was diluted with water so that the concentration of the compound of the present invention reaches 500 ppm to prepare a chemical solution for test. 10 ml of the chemical solution for test was irrigated to the plant feet of bok choy seedlings (extending period of 7 major leaves) raised in No. 3 pots, followed by keeping them in a warm room with a temperature of 25° C. for 7 days. The bok choy seedlings were placed in a glass warm room and 300 adult Plutella xylostella were released to 50 bok choy seedlings. After 7 days were passed from releasing the insects, the number of living larvae of Plutella xylostella parasitic in the bok choy seedlings was investigated and the prevention rate was calculated by the following equation. The test was repeated twice.

Prevention rate=[1−(Nt)/(Nc)]×100

[0441] Nt: number of parasites in spray-treatment area

[0442] Nc: number of parasites in control area

[0443] The efficacy test agains Plutella xylostella was carried out for Compounds 1-46, 1-47, 1-65, 1-69, 1-85, 1-102, 1-121, 2-5, 3-1, 6-28 and 6-53. As a result, all of the compounds demonstrated 80% or more of prevention rate against Plutella xylostella.

(Test Example 11) Efficacy Test Against Pseudaletia separate (Seed Treatment Test)

[0444] 0.1 g of each compound of the present invention was diluted with 2 ml of acetone to prepare a chemical solutions for test. 10 g of wheat seeds was added to the chemical solution for test and air dried, followed by seedling 100 seeds in a planter. After keeping the planter in a warm room with a temperature of 25° C. for 7 days, 100 first-instar larvae of Pseudaletia separate were released in the planter. The planter was kept in a war room with a temperature of 25° C., the number of living Pseudaletia separate was investigated after 3days were passed, and the prevention rate was calculated by the following equation. The test was repeated twice.

Prevention rate=[1−(Nt)/(Nc)]×100

[0445] Nt: number of parasites in spray-treatment area

[0446] Nc: number of parasites in control area

[0447] The efficacy test against the first-instar larvae of Pseudaletia separate was carried out for Compounds 1-47, 1-65, 1-69, 1-102, 2-5 and 6-53. As a result, all oft he compounds demonstrated 80% or more of prevention rate against the first-instar larvae of Pseudaletia separate.

(Test Example 12) Efficacy Test Against Rhopalosiphum padi (Seed Treatment Test)

[0448] 0.1 g of each compound of the present invention was diluted with 2 ml of acetone to prepare chemical solutions for test. 10 g of wheat seeds was added to the chemical solution for test and air dried, followed by seedling 100 seeds in a planter. After keeping the planter in a warm room with a temperature of 25° C. for 7 days, 50 adult Rhopalosiphum padi were released in the planter. The number of living Rhopalosiphum padi was investigated after 6 days were passed, and the prevention rate was calculated by the following equation. The test was repeated twice.

[0449] Prevention rate=[1−(Nt)/(Nc)]×100

[0450] Nt: number of parasites in spray-treatment area

[0451] Ne: number of parasites in control area

[0452] The efficacy test against Rhopalosiphum padi was carried out for Compounds 1-47, 1-65, 1-69, 1-102, 2-5 and 6-53. As a result, all oft he compounds demonstrated 80% or more of prevention rate against Rhopalosiphum padi.

INDUSTRIAL APPLICABILITY

[0453] The diarylimidazole compound or salt thereof according to the present invention can prevent harmful organisms which are harmful for agricultural crops and cause the problem of hygiene. Particularly, the compound or salt thereof can effectively prevent acarus and insecticides. Furthermore, the compound or salt thereof can prevent external parasites and internal parasite which are hannful for humans and animals and thereby useful for industry.