DESCRIPTION

UNSATURATED IMINE COMPOUND AND USE THEREOF FOR PEST CONTROL

Technical Field

The present invention relates to an α, β-unsaturated imine compound and use thereof for pest control .

Background Art

Until now, various compounds have been investigated for the purpose of controlling pests, and put into practical use specifically, described in Liebigs Annalen der Chemie (1980), (3), 344-357.

Japanese Patent Application National Publication (Laid-Open) No. 10-513502 describes an α, β-unsaturated imine compound useful as a coloring agent or stabilizer.

Disclosure of the Invention

The present invention has an object of providing a compound showing an excellent controlling effect on pests.

The present inventors have intensively studied and resultantIy found that an α, β-unsaturated imine compound of the following formula (I) shows an excellent controlling effect on pests, leading to the present invention.

That is, the present invention includes the following

inventions .

(1) An α, β-unsaturated imine compound of the formula (hereinafter this compound will be referred to as "the compound of the present invention" and its formula will sometimes be referred to as "the formula of the present invention" ) : •

wherein A represents a phenyl group optionally substituted with (X ² ) _q/ an aromatic hetero ring optionally substituted with a Cl to C5 alkyl group or a halogen atom, a Cl to C5 alkyl group optionally substituted with a halogen atom, or a C3 to ClO cycloalkyl group optionally substituted with a Cl to C5 alkyl group or a halogen atom, where the aromatic hetero ring forms a carbon-to-carbon bond with the main chain of the compound,

R represents a hydrogen atom or a Cl to C5 alkyl group optionally substituted with a halogen atom, each of p, q and r represents an integer of 0 to 5, X ¹ S, X ² S and X ³ S may respectively be different each other in case that p, q and r respectively represent 2 or more,

X ¹ , X ² and X ³ respectively represent -OR ¹ , -SR ¹ , - -C(=0) N(R ² JR ¹ , a Cl to Cβ chain hydrocarbon group optionally substituted with at least one of the group A, a phenyl group optionally substituted with at least one of the group B, a nitro group, a cyano group or a halogen atom, or in case that p, q or r represents 2 or more, two X ¹ S, two X ² S or two X ³ S may together form a C2 to C5 polymethylene group optionally substituted with at least one of the group B, a propene-1, 3-diyl group optionally substituted with at least one of the group B, a 1,3- butadiene-1, 4-diyl group optionally substituted with at least one of the group B, or a methylenedioxy group,

R ¹ represents a Cl to C5 chain hydrocarbon group optionally substituted with at least one of the group A,

R ² represents a Cl to C5 chain hydrocarbon group or a hydrogen atom,

R ³ represents a Cl to C6 chain hydrocarbon group optionally substituted with at least one of the group A, or a hydrogen atom, the group A consists of Cl to C5 alkyloxy groups, Cl to C5 alkylthio groups and halogen atoms, and the group B consists of Cl to C6 alkyl groups, Cl to C5 alkyloxy groups, Cl to C5 alkylthio groups and halogen atoms .

(2) The α, β-unsaturated imine compound according to (1) of the formula (I) :

(3) The a, β-unsaturated imine compound according to (1) or (2) , wherein

X ¹ , X ² and X ³ respectively represent -OR ¹ , -SR ¹ , a Cl to C6 chain hydrocarbon group optionally substituted with at least one of the group A, a phenyl group optionally substituted with at least one of the group B, a nitro group, a cyano group or a halogen atom, or in case that p, q or r represents 2 or more, two X ¹ S, two X ² S or two X ³ S may together form a C2 to C5 polymethylene group optionally substituted with at least one of the group B, a propene-1, 3-diyl group optionally substituted with at least one of the group B, a 1,3- butadiene-1, 4-diyl group optionally substituted with at least one of the group B, or a methylenedioxy group.

(4) The α, β-unsaturated imine compound according to any one of (1) to (3), wherein

X ¹ , X ² and X ³ respectively represent a Cl to Cβ alkyl

group optionally substituted with at least one of the group A, -OR ¹ , a phenyl group optionally substituted with at least one of the group B, a nitro group, a cyano group or a halogen atom, or in case that p, q or r represents 2 or more, two X ¹ S, two X ² S or two X ³ S may together form a C2 to C5 polymethylene group, a propene-1, 3-diyl group, or a 1,3- butadiene-1, 4-diyl group,

R ¹ represents a Cl to C5 alkyl group optionally substituted with at least one of the group A. (5) The α, β-unsaturated imine compound according to any one of (1) to (4) , wherein

X ¹ represents a Cl to C6 alkyl group optionally substituted with a halogen atom, a Cl to C5 alkyloxy group optionally substituted with a halogen atom, a nitro group or a halogen atom.

(6) The α, β-unsaturated imine compound according to any one of (1) to (5) , wherein

X ² represents a nitro group, a halogen atom, a Cl to C6 alkyl group optionally substituted with a halogen atom, a Cl to C5 alkyloxy group optionally substituted with a halogen atom, or a phenyl group optionally substituted with at least one of the group consisting of Cl to C6 alkyl groups, Cl to C5 alkyloxy groups and halogen atoms. (7) The α, β-unsaturated imine compound according to any

one of (1) to (6) , wherein

X ³ represents a Cl to C6 alkyl group optionally substituted with a halogen atom, a Cl to C5 alkyloxy group optionally substituted with a halogen atom, a halogen atom, or a phenyl group optionally substituted with at least one of the group consisting of Cl to C6 alkyl groups, Cl to C5 alkyloxy groups and halogen atoms, or a C2 to C5 polymethylene group formed by two X ³ S together. (8) The α, β-unsaturated imine compound according to any one of (1) to (7) , wherein

X ¹ represents a Cl to C6 alkyl group optionally substituted with a halogen atom, a Cl to C5 alkyloxy group optionally substituted with a halogen atom, a nitro group or a halogen atom,

X ² represents a nitro group, a halogen atom, a Cl to C6 alkyl group optionally substituted with a halogen atom, a Cl to C5 alkyloxy group optionally substituted with a halogen atom, or a phenyl group optionally substituted with at least one of the group consisting of Cl to C5 alkyl groups, Cl to C5 alkyloxy groups and halogen atoms, and X ³ represents a halogen atom, a Cl to C6 alkyl group optionally substituted with a halogen atom, a Cl to C5 alkyloxy group optionally substituted with a halogen atom, or a phenyl group optionally substituted with at least one of the group consisting of Cl to C5 alkyl groups, Cl to C5

alkyloxy groups and halogen atoms, or a C2 to C5 polymethylene group formed by two X ³ S together.

(9) The α, β-unsaturated imine compound according to any one of (1) to (8) , wherein each of p, q and r represents an integer of 0 to 2.

(10) Use of the α, β-unsaturated imine compound as described in any one of (1) to (9), for controlling pests.

(11) A pesticidal composition comprising as an active ingredient the α, β-unsaturated imine compound as described in any one of (1) to (9) .

(12) A pest controlling method which comprises applying the OL, β-unsaturated imine compound as described in any one of (1) to (9) to a pest or a place where the pest inhabits.

Effect of the Invention

The compound of the present invention shows an excellent controlling effect on pests.

Best Modes for Carrying Out the Invention

Next, specific examples of the substituents in the present invention will be described below.

In the present invention, the aromatic hetero ring includes 5-membered rings or 6-membered ring having a nitrogen atom; 5-membered rings having an oxygen atom; 5- membered rings having a sulfur atom. Examples of the

above-described aromatic hetero ring include furane, thiophene, pyrrole, thiazole, imidazole, pyridine, pyrimidine and pyrazine.

In the present invention, the aromatic hetero ring forms a carbon-to-carbon bond with the main chain of the compound .

In the present invention, the halogen atom means a fluorine atom, chlorine atom, bromine atom and iodine atom.

In the present invention, examples of the Cl to C5 alkyl group include a methyl group, ethyl group, propyl group, isopropyl group, butyl group, tert-butyl group and pentyl group .

In the present invention, examples of the C3 to ClO cycloalkyl group include a cyclopropane group, cyclobutane group, cyclopentane group and cyclohexane group.

In the present invention, the group A means a group consisting of Cl to C5 alkyloxy groups, Cl to C5 alkylthio groups and halogen atoms . The group B means a group consisting of Cl to C6 alkyl groups, Cl to C5 alkyloxy groups, Cl to C5 alkylthio groups and halogen atoms.

Groups of the group A include, for example, a methoxy group, ethoxy group, propoxy group, isopropoxy group; methylthio group, ethylthio group, propylthio group, isopropylthio group; fluorine atom, chlorine atom and bromine atom.

Groups of the group B include, for example, a methyl group, ethyl group, propyl group, isopropyl group; methoxy group, ethoxy group, propoxy group, isopropoxy group; methylthio group, ethylthio group, propylthio group, isopropylthio group; fluorine atom, chlorine atom and bromine atom.

The Cl to C6 chain hydrocarbon group optionally substituted with at least one of the group A includes Cl to C6 alkyl groups optionally substituted with at least one of the group A, C2 to Cβ alkenyl groups optionally substituted with at least one of the group A and C2 to C6 alkynyl groups optionally substituted with at least one of the group A.

Examples of the Cl to C6 alkyl group optionally substituted with at least one of the group A include Cl to C6 alkyl groups such as a methyl group, a ethyl group, a propyl group, an isopropyl group, a butyl group, a tert- butyl group, or a pentyl group; Cl to C6 haloalkyl groups such as a trifluoromethyl group; and Cl to C5 alkyloxy-Cl to C6 alkyl groups such as a methoxymethyl group, a 2- methoxyethyl group, or a 2-ethoxyethyl group.

Examples of the C2 to C6 alkenyl group optionally substituted with at least one of the group A include C2 to C6 alkenyl groups such as a vinyl group, a 2-propenyl group, or a 2-butenyl group; and C2 to C6 haloalkenyl

groups such as a 1-chlorovinyl group.

Examples of the C2 to C6 alkynyl group optionally substituted with at least one of the group A include C2 to C6 alkynyl groups such as a 2-propynyl group, or a 2- butynyl group .

R ¹ represents a Cl to C5 chain hydrocarbon group optionally substituted with at least one of the group A.

R ² represents a Cl to C5 chain hydrocarbon group or hydrogen atom.

R ³ represents a Cl to C6 chain hydrocarbon group optionally substituted with at least one of the group A, or a hydrogen atom.

The above-described Cl to C5 chain hydrocarbon group includes Cl to C5 alkyl groups, C3 to C5 alkenyl groups and C3 to C5 alkynyl groups .

In the present invention, examples of the C3 to C5 alkenyl group include a 2-propenyl group and 2-butenyl group .

In the present invention, examples of the C3 to C5 alkynyl group include a 2-propynyl group and 2-butynyl group .

The -OR ¹ includes Cl to C5 alkyloxy groups optionally substituted with at least one of the group A, C3 to C5 alkenyloxy groups optionally substituted with at least one of the group A and C3 to C5 alkynyloxy groups optionally

substituted with at least one of the group A.

Examples of the Cl to C5 alkyloxy group optionally substituted with at least one of the group A include Cl to C5 alkyloxy groups such as a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, a butoxy group, a tert-butoxy group, or a pentyloxy group; and Cl to C5 haloalkyloxy groups such as a trifluoromethoxy group.

Examples of the C3 to C5 alkenyloxy group optionally substituted with at least one of the group A include C3 to C5 alkenyloxy groups such as a 2-propenyloxy group.

Examples of the C3 to C5 alkynyloxy group optionally substituted with at least one of the group A include C3 to C5 alkynyloxy groups such as a 2-propynyloxy group.

The -SR ¹ includes Cl to C5 alkylthio groups optionally substituted with at least one of the group A, C3 to C5 alkenylthio groups optionally substituted with at least one of the group A and C3 to C5 alkynylthio groups optionally substituted with at least one of the group A.

Examples of the Cl to C5 alkylthio group optionally substituted with at least one of the group A include Cl to C5 alkylthio groups such as a methylthio group, ethylthio group, propylthio group, isopropylthio group, or butylthio group .

Examples of the C3 to C5 alkenylthio group optionally substituted with at least one of the group A include C3 to

C5 alkenylthio groups such as a 2-propenyloxy group.

Examples of the C3 to C5 alkynylthio group optionally substituted with at least one of the group A include C3 to C5 alkynylthio groups such as a 2-propynyloxy group.

Examples of -N (R ² ) R ¹ include Cl to C5 alkylamino groups such as a methylamino group, ethylamino group; and di (Cl to C5 alkyl) amino groups such as a dimethylamino group, or a diethylamino group.

The -N(R ² ) C(=O)R ³ includes a formylamino group; (Cl to C3 alkyl) carbonylamino groups such as an acetylamino group; and N-(Cl to C5 alkyl) - (Cl to C3 alkyl) carbonylamino groups such as an N-methylacetylamino group .

The -Ct=O)OR ¹ includes (Cl to C5 alkyloxy) carbonyl groups such as a methoxycarbonyl group, or an ethoxycarbonyl group .

The -C(=0) N(R ² )R ¹ includes a carbamoyl group; N-(Cl to C5 alkyl) carbamoyl groups such as an N-methylcarbamoyl group; and N,N-di(Cl to C5 alkyl) carbamoyl groups such as an N,N-dimethylcarbamoyl group.

The phenyl group optionally substituted with at least one of the group B includes a phenyl group, 4-methylphenyl group, 4-chlorophenyl group and 4-fluorophenyl group.

The C2 to C5 polymethylene group optionally substituted with at least one of the group B includes an ethylene group, propane-1, 3-diyl group, namely trimethylene

group, butane-1, 4-diyl group, namely tetramethylene group, and 2, 2, 3, 3 -tetramethylbutane-1, 4-diyl group.

Examples of the propene-1, 3-diyl group optionally substituted with at least one of the group B include a propene-1, 3-diyl group and 2 -methyl-1-propene-1, 3-diyl group.

Examples of the 1, 3 -butadiene-1, 4-diyl group optionally substituted with at least one of the group B include a 1, 3 -butadiene-1, 4-diyl group, 2-methyl-l, 3- butadiene-1, 4-diyl group, 2-chloro-l, 3 -butadiene-1, 4-diyl group and 2 , 3-dichloro-l, 3 -butadiene-1, 4-diyl group.

As the compound of the present invention, preferable are compounds in which A is a phenyl group optionally substituted with (X ² ) _q and R is a hydrogen atom, that is the compounds (I) of the formula (I) :

[wherein, X ¹ , X ² , X ³ , p, q and r are as defined above] .

The above-described compound (I) has a phenyl group optionally substituted with (X ¹ J _p , a phenyl group

optionally substituted with (X ² ) _g and a phenyl group optionally substituted with (X ³ ) _r .

Suitable examples of the phenyl group optionally substituted with (X ¹ Jp include a phenyl group, 2- fluoropheny1 group, 3 -fluoropheny1 group, 4-fluorophenyl group, 2-chlorophenyl group, 3-chlorophenyl group, 4- chlorophenyl group, 2-bromophenyl group, 3-bromophenyl group, 4-bromophenyl group, 2 -methylphenyl group, 3- methylphenyl group, 4 -methylphenyl group, 2- trifluoromethylphenyl group, 3-trifluoromethylphenyl group, 4-trifluoromethylphenyl group, 2-methoxyphenyl group, 3- methoxyphenyl group, 4 -methoxyphenyl group, 2- (methylthio) phenyl group, 4- (methylthio) phenyl group, 2- nitrophenyl group, 3-nitrophenyl group, 4-nitrophenyl group, 2 -cyanopheny1 group, 3 -cyanophenyl group, 4- cyanophenyl group, 4-phenylphenyl group, 2, 4-difluorophenyl group, 3 , 4-difluorophenyl group, 3 , 5-difluorophenyl group, 2, 4-dichlorophenyl group, 3 , 4-dichlorophenyl group, 3,5- dichlorophenyl group, 2 , 4-dimethylphenyl group, 3,4- dimethylphenyl group, 3 , 5-dimethylphenyl group, 4-indanyl group, 5-indanyl group, 1, 2, 3 , 4-tetrahydronaphthalen-5-yl group, 1, 2 , 3 , 4-tetrahydronaphthalen-6-yl group, 5-indenyl group, 6-indenyl group, l-naphthyl group, 2-naphthyl group, 2-fluoro-4-methylphenyl group, 3 -fluoro-4 -methylphenyl group, 4-fluoro-2-methylphenyl group, 4-fluoro-2-

methylphenyl group, 2-chloro-4-methγlphenyl group, 3- chloro-4-methylphenyl group, 2-chloro-4- trifluoromethylphenyl group, 3-chloro-4~ trifluoromethylphenyl group, 2-fluoro-4-methoxyphenyl group, 3 -fluoro-4-methoxyphenyl group, and

4 -chloro-3-methoxyphenyl group.

Suitable examples of the phenyl group optionally substituted with (X ² ) _q include a phenyl group, 2- fluorophenyl group, 3 -fluorophenyl group, 4-fluorophenyl group, 2-chlorophenyl group, 3-chlorophenyl group, 4- chlorophenyl group, 2-bromophenyl group, 3-bromophenyl group, 4-bromophenyl group, 2-methylphenyl group, 3- methylphenyl group, 4 -methylphenyl group, 4-isopropylphenyl group, 2-trifluoromethylphenyl group, 3- trifluoromethylphenyl group, 4 -trifluoromethylphenyl group, 2 -methoxyphenyl group, 3 -methoxyphenyl group, 4- methoxyphenyl group, 2- (methylthio) phenyl group, 4- (methylthio) phenyl group, 2-nitrophenyl group, 3- nitrophenyl group, 4-nitrophenyl group, 2-cyanophenyl group, 3 -cyanophenyl group, 4 -cyanophenyl group, 4- phenylpheny1 group, 2 , 4-difluoropheny1 group, 3,4- difluorophenyl group, 3 , 5-difluorophenyl group, 2,6- difluorophenyl group, 2 , 4-dichlorophenyl group, 3,4- dichloropheny1 group, 3 , 5-dichlorophenyl group, 2,3- dichlorophenyl group, 2 , 4-dimethylphenyl group, 3,4-

dimethylphenyl group, 3 , 5-dimethylphenyl group, 4-indanyl group, 5-indanyl group, 1, 2 , 3 , 4-tetrahydronaphthalen-5-yl group, 1, 2 , 3 , 4-tetrahydronaphthalen-6-yl group, 5-indenyl group, 6-indenyl group, 1-naphthyl group, 2-naphthyl group, 2-fluoro-4-methylphenyl group, 3-fluoro-4-methylphenyl group, 4-fluoro-2-methylphenyl group, 4-fluoro-2- methylphenyl group, 2-chloro-4-τnethylphenyl group, 3- chloro-4-methylphenyl group, 2-chloro-4- trifluoromethylphenyl group, 3-chloro-4- trifluoromethylphenyl group, 2-fluoro-4-methoxyphenyl group, 3-fluoro-4-methoxyphenyl group, and 4-chloro-3-methoxyphenyl group.

Suitable examples of the phenyl group optionally substituted with (X ³ ) _r include a phenyl group, 2-fluorophenyl group, 3-fluorophenyl group, 4 -fluorophenyl group, 2-chlorophenyl group, 3-chlorophenyl group, 4- chlorophenyl group, 2-bromophenyl group, 3-bromophenyl group, 4-bromophenyl group, 2-methylphenyl group, 3- methylphenyl group, 4 -methylphenyl group, 4-isopropylphenyl group, 2 -trifluoromethylphenyl group, 3- trifluoromethylphenyl group, 4 -trifluoromethylphenyl group, 2-methoxyphenyl group, 3-methoxyphenyl group, 4- methoxyphenyl group, 2- (methylthio) phenyl group, 4- (methylthio) phenyl group, 2-nitrophenyl group, 3- nitrophenyl group, 4-nitrophenyl group, 2-cyanopheny1

group, 3 -cyanophenyl group, 4-cyanopheny1 group, 4-phenylphenyl group, 3 , 4-difluorophenyl group, 3,5- difluorophenyl group, 3 , 4-dichlorophenyl group, 3,5- dichlorophenyl group, 3 , 4-dimethylphenyl group, 3,5- dimethylphenyl group, 4-indanyl group, 5-indanyl group, l,2,3,4-tetrahydronaphthalen-5-yl group, 1,2,3,4- tetrahydronaphthalen-6-yl group, 5-indenyl group, β-indenyl group, 1-naphthyl group, 2-naphthyl group,

2-fluoro-4-methylphenyl group, 3-fluoro-4-methylphenyl group, 4-fluoro-2-methylphenyl group, 4-fluoro-2- methylphenyl group, 2-chloro-4-methylphenyl group, 3- chloro-4-methylphenyl group, 2-chloro-4- trifluoromethylphenyl group, 3-chloro-4- trifluoromethylphenyl group, 2-fluoro-4-methoxyphenyl group, 3-fluoro-4-methoxyphenyl group, and 4-chloro-3-methoxyphenyl group.

Embodiments of the compound (I) include the following embodiments ; ex, β-unsaturated imine compounds of the formula (I) in which X ¹ represents a Cl to C6 chain hydrocarbon group optionally substituted with at least one of the group A, - OR ¹ , -SR ¹ , a phenyl group optionally substituted with at least one of the group B, a nitro group, a cyano group or a halogen atom, or in case that p is 2 or more, two X ¹ S form

together a C2 to C5 polymethylene group optionally substituted with at least one of the group B, a propene- 1,3-diyl group optionally substituted with at least one of the group B, a 1, 3 -butadiene-1, 4-diyl group optionally substituted with at least one of the group B, or a methylenedioxy group, α, β-unsaturated imine compounds of the formula (I) in which X ¹ represents a Cl to C6 alkyl group optionally substituted with at least one of the group A, -OR ¹ , a phenyl group optionally substituted with a halogen atom, a nitro group, a cyano group or a halogen atom, or two X ¹ S form together a C2 to C5 polymethylene group, a propene- 1,3 -diyl group or a 1, 3 -butadiene-1, 4 -diyl group, and R ¹ represents a Cl to C5 alkyl group optionally substituted with at least one of the group A when p is 2 or more, α, β-unsaturated imine compounds of the formula (I) in which X ¹ represents a nitro group, a halogen atom, a Cl to C6 alkyl group optionally substituted with a halogen atom, or a Cl to C5 alkyloxy group optionally substituted with a halogen atom, α, β-unsaturated imine compounds of the formula (I) in which X ² represents a Cl to C6 chain hydrocarbon group optionally substituted with at least one of the group A, - OR ¹ , -SR ¹ , a phenyl group optionally substituted with at least one of the group B, a nitro group, a cyano group or a

halogen atom, in case that q is 2 or more, two X ² form together a C2 to C5 polymethylene group optionally substituted with at least one of the group B, a propene- 1,3-diyl group optionally substituted with at least one of the group B, a 1, 3 -butadiene-1, 4-diyl group optionally substituted with at least one of the group B, or a methylenedioxy group, α, β-unsaturated imine compounds of the formula (I) in which X ² represents a Cl to C6 alkyl group optionally substituted with at least one of the group A, -OR ¹ , a phenyl group optionally substituted with a halogen atom, a nitro group, a cyano group or a halogen atom, in case that q is 2 or more, two X ² form together a C2 to C5 polymethylene group, a propene-1, 3-diyl group or a 1,3- butadiene-1, 4-diyl group, and R ¹ represents a Cl to C5 alkyl group optionally substituted with at least one of the group A, α, β-unsaturated imine compounds of the formula (I) in which X ² represents a nitro group, a halogen atom, a Cl to C6 alkyl group optionally substituted with a halogen atom, a Cl to C5 alkyloxy group optionally substituted with a halogen atom, or a phenyl group optionally substituted with at least one of the group consisting of Cl to C6 alkyl groups, Cl to C5 alkyloxy groups and halogen atoms, α, β-unsaturated imine compounds of the formula (I) in

which X ³ represents a Cl to C6 chain hydrocarbon group optionally substituted with at least one of the group A, - OR ¹ , -SR ¹ , a phenyl group optionally substituted with at least one of the group B, a nitro group, a cyano group or a halogen atom, in case that r is 2 or more, two X ³ S form together a C2 to C5 polymethylene group optionally substituted with at least one of the group B, a propene- 1,3-diyl group optionally substituted with at least one of the group B, a 1, 3 -butadiene-1, 4-diyl group optionally substituted with at least one of the group B or a methylenedioxy group, α, β-unsaturated imine compounds of the formula (I) in which X ³ represents a Cl to C6 alkyl group optionally substituted with at least one of the group A, -OR ¹ , a phenyl group optionally substituted with a halogen atom, a nitro group, a cyano group or a halogen atom, in case that r is 2 or more, two X ³ S form together a C2 to C5 polymethylene group, a propene-1, 3-diyl group or a 1,3- butadiene-1, 4-diyl group, and R ¹ represents a Cl to C5 alkyl group optionally substituted with at least one of the group A, α, β-unsaturated imine compounds of the formula (I) in which X ³ represents a Cl to C6 alkyl group optionally substituted with a halogen atom, a Cl to C5 alkyloxy group optionally substituted with a halogen atom, a phenyl group

optionally substituted with at least one of the group consisting of Cl to C6 alkyl groups, Cl to C5 alkyloxy groups and halogen atoms, a halogen atom, or a C2 to C5 polymethylene group formed by two X ³ S, a, β-unsaturated imine compounds of the formula (I) in which X ¹ , X ² and X ³ respectively represent a Cl to Cβ chain hydrocarbon group optionally substituted with at least one of the group A, -OR ¹ , -SR ¹ , a phenyl group optionally substituted with at least one of the group B, a nitro group, a cyano group or a halogen atom, or in case that p, q or r represents 2 or more, two X ¹ S, two X ² S or two X ³ S may together form a C2 to C5 polymethylene group optionally substituted with at least one of the group B, a propene- 1,3-diyl group optionally substituted with at least one of the group B, a 1, 3-butadiene-l, 4-diyl group optionally substituted with at least one of the group B or a methylenedioxy group, ex, β-unsaturated imine compounds of the formula (I) in which X ¹ , X ² and X ³ respectively represent a Cl to C6 chain hydrocarbon group optionally substituted with a halogen atom, -OR ¹ , a phenyl group optionally substituted with a halogen atom, a nitro group, a cyano group or a halogen atom, or in case that p, q or r represents 2 or more, two X ¹ S, two X ² S or two X ³ S may together form a C2 to C5 polymethylene group, a propene-1, 3-diyl group or a 1,3-

butadiene- 1, 4 -diyl group, and R ¹ represents a Cl to C5 chain hydrocarbon group optionally substituted with a halogen atom, α, β-unsaturated imine compounds of the formula (I) in which each of p, q and r represents an integer of 0 to 3 , and X ¹ S respectively represent a fluorine atom, chlorine atom, bromine atom, methyl group, trifluoromethyl group, methoxy group or nitro group, X ² S respectively represent a fluorine atom, chlorine atom, methyl group, isopropyl group, trifluoromethyl group, methoxy group, nitro group or phenyl group, and X ³ S respectively represent a fluorine atom, chlorine atom, bromine atom, methyl group, isopropyl group, trifluoromethyl group, methoxy group, nitro group or phenyl group, or a trimethylene group formed by two X ³ S, α, β-unsaturated imine compounds of the formula (I) in which the phenyl group optionally substituted with (X ¹ J _p is a phenyl group, 2-fluorophenyl group, 2-chlorophenyl group, 2-bromophenyl group, 2 -methylphenyl group, 3 -fluorophenyl group, 3-chlorophenyl group, 3-bromophenyl group, 3- methylphenyl group, 3 -trifluoromethylphenyl group, 3- methoxyphenyl group, 4 -fluorophenyl group, 4-chlorophenyl group, 4-bromophenyl group, 4 -methylphenyl group, 4- trifluorophenyl group, 4 -methoxyphenyl group, 4-nitrophenyl group, 2,4-dichlorophenyl group, 2 , 4-dimethylphenyl group or 3, 5-dichlorophenyl group, the phenyl group optionally

substituted with (X ² ) _q is a phenyl group, 2-fluorophenyl group, 2-chlorophenyl group, 2 -methylphenyl group, 3- chlorophenyl group, 3 -trifluoromethylphenyl group, 3- methylphenyl group, 3 -methoxyphenyl group, 4-fluorophenyl group, 4-chlorophenyl group, 4-methylphenyl group, 4- isopropylphenyl group, 4 -trifluorophenyl group, 4- methoxyphenyl group, 4-nitrophenyl group, 4-phenylphenyl group, 2 , 3-dichlorophenyl group, 2 , 4-difluorophenyl group, 2 , 4-dichlorophenyl group, 2, 4-dimethylphenyl group, 2,6- difluorophenyl group, 3 , 4-difluorophenyl group, 3,4- dichlorophenyl group, 3 , 4-dimethylphenyl group, 3,5- difluorophenyl group, 3 , 5-dichlorophenyl group or 3,5- dimethylphenyl group, and the phenyl group optionally substituted with (X ³ ) _r is a phenyl group, 2-methylphenyl group, 3 -fluorophenyl group, 3-chlorophenyl group, 3- methylphenyl group, 4-fluorophenyl group, 4-chlorophenyl group, 4-bromophenyl group, 4 -methylphenyl group, 4- isopropylphenyl group, 4-trifluoromethylphenyl group, 4- methoxyphenyl group, 4-phenylphenyl group, 3,4- dimethylphenyl group or 5 - indanyl group .

Next, the method for producing the compound of the present invention will be described.

The compound of the present invention can be produced, for example, by the following production method.

Production Method 1

Among the compounds of the present invention, a compound in which R=H in the formula of the present invention can be produced by reacting the compound of the formula (II) (hereinafter described as compound (II) ) :

HC=C

(wherein, A, X ³ and r respectively represent the same meanings as described above . ) with the compound of the formula (III) (hereinafter, described as compound (III) ) :

(wherein, X ¹ and p respectively represent the same meanings as described above . ) .

In this reaction, the amount of the compound (III) is theoretically 1 equivalent with respect to the compound

(II) , however, large excess amounts may also be permissible, and it is preferably 0.8 to 5 equivalents, more preferably 0.7 to 1.2 equivalents to the compound

(ID .

This reaction can be carried out in the presence of a suitable solvent . Examples of such a solvent include alcohols such as methanol, ethanol , or isopropanol ; aliphatic hydrocarbons such as pentane, hexane, heptane, or petroleum ether; aromatic hydrocarbons such as benzene, toluene, or xylene; esters such as methyl acetate, ethyl acetate, ethyl formate, or ethyl propionate; ketones such as acetone, or methylethylketone; ethers such as diethylether, dipropylether, diisopropylether, dibutylether, tetrahydrofuran, or dioxane; nitriles such as acetonitrile, or propionitrile; acid amides such as dimethylformamide, or dimethylacetamide; sulfoxides such as dimethyl sulfoxide; sulfones such as sulfolane; phosphoric amides such as hexamethylphosphoramide; halogenated hydrocarbons such as dichloromethane, chloroform, 1,2- dichloroethane, or carbon tetrachloride; and aromatic amines such as pyridine, picoline, lutidine, or quinoline. These solvents may be used in admixture, and may also be used as a mixed solvent with water.

Further, in this reaction, a base or an acid may be present in the reaction system, if necessary.

In the case that a base is present, examples of such a base include alkali metal alcoholates such as sodium ethylate, sodium methylate, or potassium tert-butoxide; nitrogen-containing organic compounds such as

triethylamine, diisopropylethylamine, pyridine, 4- dimethylaminopyridine, or N,N-dimethylaniline; carbonates such as potassium carbonate, sodium carbonate, sodium hydrogen carbonate, or potassium hydrogen carbonate; hydroxides such as sodium hydroxide, or potassium hydroxide; metal hydrides such as lithium hydride, sodium hydride, or potassium hydride; and organolithiums such as butyllithium, or lithiumdiisopropylamide . The amount of the base to be used is not particularly restricted providing it does not exert a reverse influence on the reaction, and it is preferably 0.01 to 0.5 equivalents, more preferably 0.01 to 0.2 equivalents to the compound (ID -

Examples of such an acid include mineral acids such as hydrochloric acid, sulfuric acid, or nitric acid; organic acids such as formic acid, acetic acid, propionic acid, trifluoroacetic acid, methanesulfonic acid, benzenesulfonic acid, or p-toluenesulfonic acid; acid addition salts of amines such as triethylamine hydrochloride, or pyridine hydrochloride; and Lewis acids such as aluminum chloride, zinc chloride, zinc iodide, titanium tetrachloride, cerium chloride, ytterbium triflate, or boron trifluoride-ether complex. The amount of the acid to be used is not particularly restricted providing it does not exert a reverse influence on the reaction, and it is preferably

0.01 to 0.5 equivalents, more preferably 0.01 to 0.2 equivalents to the compound (II) .

The reaction temperature of this reaction is usually - 50 to 150°C, preferably -20 to 100°C, more preferably -10 to 50°C. The reaction time is usually 0.1 to 96 hours, preferably 0.1 to 24 hours.

After completion of the present reaction, the compound of the present invention can be isolated by concentrating the reaction mixture; or by pouring the reaction mixture into water, then, extracting with an organic solvent, and performing usual post-treatment operations such as concentration. The resultant compound of the present invention can be purified by conventional methods, for example, distillation, re-precipitation, re- crystallization, or chromatography, in some cases.

The compound (II) is a known compound. When A is a phenyl group optionally substituted with (X ² ) _q , namely the compound of the formula:

(wherein, X ² , X ³ , q and r represent the same meanings as

described above . ) , the compound (II) can be produced from the compound of the formula (IV-I) :

(wherein, Si ^a represents a trialkylsilyl such as trimethylsilyl, or triethylsilyl, and X ² , X ³ , q and r respectively represent the same meanings as described above . ) .

The compound (IV-I) is a known compound, or it can be produced by known methods, for example, a method described in J. Org. Chem, 1981, 46, 2280-2286, or J. Am. Chem. Soc, 2006, 128(14), 4592-4593.

The compound (III) is a known compound, or it can be produced by known methods .

Production Method 2

Among the compounds of the present invention, a compound in which R=H in the formula of the present invention can also be produced by a production method comprising a step (2-1) of reacting the compound of the formula

( IV) (hereinafter described as compound ( IV) ) :

(wherein Si ^a represents a trialkylsilyl such as trimethylsilyl, or triethylsilyl, and A, X ³ and r respectively represent the same meanings as described above . ) with the compound of the formula (III) to produce the compound of the formula (V) (hereinafter described as compound (V) ) :

(wherein Si ^a , X ¹ , X ³ , p and r respectively represent the same meanings as described above.) and a step (2-2) of de-trialkylsilylating the compound (V) .

In the reaction of the step (2-1) , the amount of the compound (III) may be a large excess amount, and preferably 0.8 to 5 equivalents, more preferably 0.7 to 1.2 equivalents to the compound (IV) .

In the reaction of the step (2-1) , a base or an acid may be present in the reaction system, if necessary.

Such a base includes for example, alkali metal alcoholates such as sodium ethylate, sodium methylate, or potassium tert-butoxide; nitrogen-containing organic compounds such as triethylamine, diisopropylethylamine, pyridine, 4-dimethylaminopyridine, or N,N-dimethylaniline; carbonates such as potassium carbonate, sodium carbonate, sodium hydrogen carbonate, or potassium hydrogen carbonate; hydroxides such as sodium hydroxide, or potassium hydroxide; metal hydrides such as lithium hydride, sodium hydride, or potassium hydride; and organolithiums such as butyllithium, or lithiumdiisopropylamide . The amount of the base to be used is not particularly restricted providing it does not exert a reverse influence on the reaction, and preferably 0.01 to 0.5 equivalents, more preferably 0.01 to 0.2 equivalents to the compound (IV) .

Such an acid includes, for example, mineral acids such as hydrochloric acid, sulfuric acid, or nitric acid; organic acids such as formic acid, acetic acid, propionic acid, trifluoroacetic acid, methanesulfonic acid, benzenesulfonic acid, or p-toluenesulfonic acid; acid addition salts of amines such as triethylamine hydrochloride, or pyridine hydrochloride; and Lewis acids such as aluminum chloride, zinc chloride, zinc iodide,

titanium tetrachloride, cerium chloride, ytterbium triflate, or boron trifluoride-ether complex. The amount of the acid to be used is not particularly restricted providing it does not exert a reverse influence on the reaction, and preferably 0.01 to 0.5 equivalents, more preferably 0.01 to 0.2 equivalents to the compound (IV) . The reaction of the step (2-1) can be carried out in the presence of a suitable solvent . Examples of such a solvent include alcohols such as methanol, ethanol, or isopropanol; aliphatic hydrocarbons such as pentane, hexane, heptane, or petroleum ether; aromatic hydrocarbons such as benzene, toluene, or xylene; esters such as methyl acetate, ethyl acetate, ethyl formate, or ethyl propionate; ketones such as acetone, or methylethylketone; ethers such as diethylether, dipropylether, diisopropylether, dibutylether, tetrahydrofuran, or dioxane; nitriles such as acetonitrile, or propionitrile; acid amides such as dimethylformamide, or dimethylacetamide; sulfoxides such as dimethyl sulfoxide; sulfones such as sulfolane; phosphoric amides such as hexamethylphosphoramide ; halogenated hydrocarbons such as dichloromethane, chloroform, 1,2- dichloroethane, or carbon tetrachloride; and aromatic amines such as pyridine, picoline, lutidine, or quinoline. These solvents may be used in admixture, and may also be used as a mixed solvent with water.

The reaction temperature of the step (2-1) is usually -50 to 150°C, preferably -20 to 100°C, more preferably -10 to 5O ⁰ C. The reaction time is usually 0.1 to 96 hours, preferably 0.1 to 24 hours.

In the step (2-2) , the de-trialkylsilylation reaction can be carried out by allowing a base to act on the compound (V) .

The reaction of the step (2-2) can be carried out in the presence of a suitable solvent. Examples of such a solvent include the same solvents as in the step (2-1) . These solvents may be used in admixture, and may also be used as a mixed solvent with water.

As the base in the step (2-2) , for example, the same bases as in the step (2-1) are mentioned. The amount of the base to be used is not particularly restricted providing it does not exert a reverse influence on the reaction, and preferably 0.01 to 5 equivalents, more preferably 0.1 to 1.5 equivalents to the compound (IV) .

The reaction temperature of the step (2-2) is usually -20 to 150°C, preferably 0 to 120°C, more preferably 10 to 80°C. The reaction time is usually 0.1 to 96 hours, preferably 0.1 to 24 hours .

After completion of the reaction of the step (2-2) , the compound of the present invention can be isolated by concentrating the reaction mixture; or by pouring the

reaction mixture into water, extracting with an organic solvent, then, performing usual post-treatment operations such as concentration. The resultant compound of the present invention can be purified by conventional methods, for example, distillation, re-precipitation, re- crystallization, or chromatography.

In Production method 2, the compound of the present invention can be produced also by confirming production of the compound (V) in the step (2-1) , then, performing the de-trialkylsilylation reaction of the step (2-2) without isolation and purification of the compound (V) .

Production Method 3

Among the compounds of the present invention, a compound in which A represents a phenyl group optionally substituted with (X ² ) _q or an aromatic hetero ring optionally substituted with a Cl to C5 alkyl group or a halogen atom can be produced, for example, by the following production method.

The production method comprises a step (3-1) of reacting the compound of the formula (hereinafter described as compound (VI) ) :

i

(wherein, A represents a phenyl group optionally substituted with (X ² ) _q or an aromatic hetero ring optionally substituted with a Cl to C5 alkyl group or a halogen atom, and R represents a hydrogen atom or a Cl to C5 alkyl group optionally substituted with a halogen atom) with a compound (III) to obtain the compound of the formula

(VII) (hereinafter described as compound (VII) ) :

(wherein, A, R, X ¹ and p respectively represent the same meanings as described above . ) , a step (3-2) of reacting the compound (VII) and the compound of the formula (VIII) (hereinafter described as compound (VIII)):

(wherein, X ³ and r respectively represent the same meanings as described above) to obtain the compound of the formula (IX) (hereinafter, described as compound (IX) ) :

(wherein, A, R, X ¹ , X ³ , p and r respectively represent the same meanings as described above.),

a step (3-3) of halogenating the compound (IX) to obtain the compound of the formula (X) (hereinafter, described as compound (X) ) :

X ¹ , X ³ , p and r represent the same meanings as described above. X represents a halogen atom.)/ and a step (3-4) of de-halogenating the compound (X) to obtain the compound of the present invention.

In the step (3-1) , the amount of the compound (III) may be a large excess amount, and preferably 0.8 to 5 equivalents, more preferably 0.7 to 1.2 equivalents to the compound (VI) .

In the reaction of the step (3-1) , a base or an acid may be present in the reaction system, if necessary.

As such a base or acid, for example, the same bases and acids as in the step (2-1) are mentioned. The amount of the base to be used is not particularly restricted providing it does not exert a reverse influence on the reaction, and preferably 0.01 to 0.5 equivalents, more preferably 0.01 to 0.2 equivalents to the compound (VI). The amount of the acid to be used is not particularly restricted providing it does not exert a reverse influence on the reaction, and preferably 0.01 to 0.5 equivalents, more preferably 0.01 to 0.2 equivalents to the compound

(VI ) .

The reaction of the step (3-1) can be carried out in the presence of a suitable solvent. As such a solvent, for example, the same solvents as in the step (2-1) are mentioned. These solvents may be used in admixture, or as a mixed solvent with water.

The reaction temperature of the step (3-1) is usually -50 to 150 ⁰ C, preferably -20 to 100 ⁰ C, more preferably -10 to 50 ⁰ C. The reaction time is usually 0.1 to 96 hours, preferably 0.1 to 24 hours.

After completion of the reaction of the step (3-1) , the compound (VII) can be isolated by concentrating the reaction mixture; or by pouring the reaction mixture into water, extracting with an organic solvent, then, performing usual post-treatment operations such as concentration. The resultant compound (VII) can be purified by conventional methods, for example, distillation, re-precipitation, re- crystallization, or chromatography.

The compound (VI) is a known compound, or it can be produced by known methods, for example, a method described in J. Chem. Soc . Perkin Trans. 1, 1793 .1988, Synthesis 1984, 339-345, and other methods.

In the reaction of the step (3-2) , the amount of the compound (VIII) may be a large excess amount, and preferably 0.8 to 5 equivalents, more preferably 0.7 to 1.2

equivalents to the compound (VII) .

The reaction of the step (3-2) can be carried out in the presence of a suitable solvent. Examples of such a solvent include the same solvents as in the step (2-1) . These solvents can also be used in admixture. In this step, it is preferable to remove water generated in the reaction system. The method for removing water includes a method of removing water out of the reaction system by azeotropic distillation with a solvent, and a method of adding a dehydrating agent such as molecular sieve into the reaction system.

In the reaction of the step (3-2) , the presence of a catalyst is not essential, however, the reaction is accelerated by addition of an acid or base, in some cases.

The acid may be an organic acid or an inorganic acid. Examples of the organic acid include formic acid, acetic acid and propionic acid, and these can be used also as a solvent. Examples of the inorganic acid include hydrochloric acid, sulfuric acid, methanesulfonic acid, benzenesulfonic acid, P-toluenesulfonic acid, and Lewis acids such as cerium chloride, aluminum chloride, zinc chloride, titanium tetrachloride, or boron trifluoride- diethylether complex. Of them, sulfuric acid, polyphosphates and the like can be used as both a solvent and as a dehydrating agent.

Examples of such a base include inorganic bases such as potassium hydroxide, sodium hydroxide, or sodium methoxide and organic bases such as pyridine, or triethylamine, and of them, organic bases can be used also as a solvent .

The reaction temperature of the step (3-2) is usually 0 to 200 ⁰ C, preferably 20 to 150°C, more preferably 30 to 100°C. The reaction time is usually 0.1 to 96 hours, preferably 0.1 to 24 hours.

After completion of the reaction of the step (3-2) , the compound (IX) can be isolated by concentrating the reaction mixture; or by pouring the reaction mixture into water, extracting with an organic solvent, then, performing usual post-treatment operations such as concentration. The resultant compound (IX) can be purified by conventional methods, for example, distillation, re-precipitation, re- crystallization or chromatography.

In the reaction of the step (3-3), halogenating agent includes chlorine, bromine, iodine, thionyl chloride, thionyl bromide, N-chlorosuccinimide, N-bromosuccinimide and N-iodosuccinimide. The amount of the halogenating agent to be used is usually 0.7 to 2.0 equivalents, preferably 0.8 to 1.5 equivalents to the compound (IX).

The reaction of the step (3-3) can be carried out in the presence of a suitable solvent . Examples of such a

solvent include the same solvents as in the step (2-1) . These solvents may be used in admixture, or may be used also as a mixed solvent with water.

The reaction temperature of the step (3-3) is usually -50 to 150 ⁰ C, preferably -20 to 100°C, more preferably -10 to 50°C. The reaction time is usually 0.1 to 96 hours, preferably 0.1 to 24 hours.

After completion of the reaction of the step (3-3), the compound (X) can be isolated by concentrating the reaction mixture; or by pouring the reaction mixture into water, extracting with an organic solvent, then, performing usual post-treatment operations such as concentration. The resultant compound (X) can be purified by conventional methods, for example, distillation, re-precipitation, re- crystallization or chromatography.

In the dehalogenating reaction of the step (3-4), a compound (I) can be produced by allowing a base to act on the compound (X) .

Examples of such a base include alkali metal alcoholates such as sodium ethylate, sodium methylate, or potassium tert-butoxide; nitrogen-containing organic compounds such as triethylamine, diisopropylethylamine, pyridine, 4-dimethylaminopyridine, or N, N-dimethylaniline ; carbonates such as potassium carbonate, sodium carbonate, sodium hydrogen carbonate, or potassium hydrogen carbonate;

hydroxides such as sodium hydroxide, or potassium hydroxide; metal hydrides such as lithium hydride, sodium hydride, or potassium hydride; and organolithiums such as butyllithium, or lithiumdiisopropylamide . The amount of the base to be used is not particularly restricted providing it does not exert a reverse influence on the reaction, and it is preferably 0.5 to 5 equivalents, more preferably 0.8 to 2.0 equivalents to the compound (X) .

The reaction of the step (3-4) can be carried out in the presence of a suitable solvent . Examples of such a solvent include the same solvents as in the step (2-1) . These solvents may be used in admixture, or may be used also as a mixed solvent with water.

The reaction temperature of the step (3-4) is usually -50 to 150°C, preferably -20 to 100 ⁰ C, more preferably -10 to 50 ⁰ C. The reaction time is usually 0.1 to 96 hours, preferably 0.1 to 24 hours.

After completion of the reaction of the step (3-4), the compound of the present invention can be isolated by concentrating the reaction mixture; or by pouring the reaction mixture into water, extracting with an organic solvent, then, performing usual post-treatment operations such as concentration. The resultant compound of the present invention can be purified by conventional methods, for example, distillation, re-precipitation, re-

crystallization or chromatography.

The compound of the present invention may exist as various isomers including geometric isomers and stereoisomers. All isomers of the compound of the present invention and a mixture of the isomers are indluded in the scope of the present invention.

The compound of the present invention has an excellent controlling effect on pests including hygiene pests, animal parasitic pests and plant parasitic pests, and thus it is effective for pest control. The compound of the present invention exerts an excellent controlling effect on pests when the compound is applied directly to the pests or to places where the pests inhabit.

A pesticidal composition comprising as an active ingredient the compound of the present invention falls within the scope of the present invention.

When the compound of the present invention is used as a composition for pest control, that is, the pesticidal composition, the compound of the present invention may be used as it is. However, the compound of the present invention is usually formulated into forms which usual agrichemicals or animal drugs may take, and then used. In other words, the pesticidal composition of the present invention may be the compound of the present invention

itself, and however, it usually comprises the compound of the present invention and additives to take a suitable form for usual agrichemicals or animal drugs. Specifically, the compound of the present invention is dissolved or dispersed in a suitable liquid carrier, mixed with a suitable solid carrier and/or a suitable gaseous carrier, or adsorbed on a suitable solid carrier to prepare the pesticidal composition of the present invention in the form of an emulsifiable concentrate, a liquid formulation, a microemulsion, a flowable formulation, an oil solution, a wettable powder, a dust, a granule, a microgranule, a seed- coating agent, a seed-immersion solution, a smoking pesticide, a tablet, a microcapsule, a spray, an aerosol, a carbon dioxide gas formulation, a heating fumigant such as a mosquito coil, an electric mosquito mat or an electric mosquito liquid, EW formulation, an ointment, a poison bait, a capsule, a pellet, a film, an injectable, a liniment, a resin formulation, a shampoo formulation or the like. The pesticidal composition of the present invention may further contain an emulsifier, a suspending agent, a spreading agent, a penetrating agent, a wetting agent, a thickener, a stabilizer, a dispersant or the like., The pesticidal composition of the present invention can be prepared by a known method.

Examples of the liquid carrier include water, alcohols

(e.g., methyl alcohol, ethyl alcohol, n-propyl alcohol, isopropyl alcohol, butyl alcohol, hexyl alcohol, benzyl alcohol, ethylene glycol, propylene glycol, or phenoxyethanol) , ketones (e.g., acetone, methyl ethyl ketone, methyl isobutyl ketone, or cyclohexanone) , ethers (e.g., diisopropyl ether, 1, 4-dioxane, tetrahydrofuran, ethylene glycol monomethyl ether, ethylene glycol dimethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, propylene glycol monomethyl ether, dipropylene glycol monomethyl ether, or 3-methoxy-3-methyl- 1-butanol) , aliphatic hydrocarbons (e.g., hexane, cyclohexane, kerosene, fuel oil, or machine oil) , aromatic hydrocarbons (e.g., toluene, xylene, ethylbenzene, dodesylbenzene, phenylxylylethane, solvent naphtha, or methylnaphthalene) , halogenated hydrocarbons (e.g., dichloromethane, trichloroethane, chloroform, or carbon tetrachloride), acid amides (e.g., N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, or N- octylpyrrolidone) , esters (e.g., butyl lactate, ethyl acetate, butyl acetate, isopropyl myristate, ethyl oleate, diisopropyl adipate, diisobutyl adipate, propylene glycol monomethyl ether acetate, fatty acid glycerin ester, or γ- butyrolactone) , nitriles (e.g., acetonitrile, isobutyronitrile, or propionitrile) , carbonates (e.g., propylene carbonate), and vegetable oils (e.g., soybean

oil, olive oil, linseed oil, coconut oil, palm oil, peanut oil, malt oil, almond oil, sesame oil, mineral oil, rosmarine oil, geranium oil, rapeseed oil, cottonseed oil, corn oil, safflower oil, or orange oil) . These liquid carriers may be used alone, or two or more, preferably one to three of these liquid carriers may be mixed in appropriate proportions and then used.

Examples of the solid carrier (e.g., a diluent or a filler) include vegetable powders (e.g., soybeen powder, tobacco powder, flour, or wood powder) , mineral powders (e.g., kaolin, Fubasami, bentonite, clay such as acid clay, talc such as talcum powder or agalmatolite powder, diatomaceous earth, silica such as mica powder) , synthetic hydrated silicon oxide, talc, ceramics, other inorganic minerals (e.g., sericite, quartz, or hydrated silica), chemical fertilizers (e.g., ammonium sulfate, ammonium phosphate, ammonium nitrate, ammonium chloride, or urea ) , alumina, sulfur powder, activated carbon, calcium carbonate, potassium chloride, sodium hydrogen carbonate, and lactose. These solid carriers may be used alone, or two or more, preferably one to three of these solid carriers may be mixed in appropriate proportions and then used.

Examples of the gaseous carrier include fluorocarbon, butane gas, LPG (liquefied petroleum gas) , dimethyl ether,

and carbon dioxide gas . These gaseous carriers may be used alone, or two or more of these gaseous carriers may be mixed in appropriate proportions and then used. Alternatively, one or more of these gaseous carriers may be used in combination with a suitable liquid carrier.

In the case where the compound of the present invention is formulated into an ointment, examples of a base material for the ointment include polyethylen glycol, pectin, esters of higher fatty acid and polyalcohol such as glyceryl monostearate ester, cellulose derivatives such as methylcellulose, sodium alginate, bentonite, higher alcohol, polyalcohol such as glycerin, petrolatum, white petrolatum, liquid paraffin, lard, vegetable oils, lanolin, anhydrous lanoiln, hydrogenated oils, and resin. These base materials may be used alone, or two or more, preferably one to three of these base materials may be used in combination. Further, a surfactant as listed below may be added to the base material .

A surfactant may be used as an emulsifier, a spreading agent, a penetrating agent, a dispersant or the like in preparing the pesticidal composition of the present invention. Examples of the surfactant include soap; and nonionic and anionic surfactants such as polyoxyethylene alkyl aryl ether [NOIGEN (trade name) , E A142 (trade name) manufactured by DAI-ICHI KOGYO SEIYAKU CO., LTD.; NONAL

(trade name) manufactured by TOHO CHEMICAL INDUSTRY CO., LTD.], alkyl sulfate [e.g. EMAL 10 (trade name) and EMAL 40 (trade name) manufactured by KAO CORPORATION] , alkylbenzene sulfonate [e.g. NEOGEN (trade name) and NEOGEN T (trade name) manufactured by DAI-ICHI KOGYOU SEIYAKU CO., LTD.; NEIPELEX (trade name) manufactured by KAO CORPORATION] , polyethylene glycol ether [e.g., NONIPOL 85 (trade name), NONIPOL 100 (trade name) , and NONIPOL 160 (trade name) manufactured by SANYO KASEI] , polyoxyethylene alkyl ether [e.g. NOIGEN ET-135 (trade name) manufactured by DAI-ICHI KOGYO SEIYAKU CO., LTD.], polyoxyethylene polyoxypropylene block polymer [e.g. NEWPOLE PE- 64 (trade name) manufactured by SANYO CHEMICAL INDUSTRIES LTD.], polyalcohol ester [e.g. TWEEN 20 (trade name) and TWEEN 80 (trade name) manufactured by KAO CORPORATION] , alkyl sulfosuccinate [e.g. SANMOLIN OT20 (trade name) manufactured by SANYO CHEMICAL INDUSTRIES LTD.; NEWKALGEN EX70 (trade name) manufactured by TAKEMOTO OIL & FAT CO., LTD.], alkyl naphthalenesulfonate [NEWKALGEN WG-I (trade name) manufactured by TAKEMOTO OIL & FAT CO., LTD.], and alkenyl naphthalenesulfonate [SORPOL 5115 (trade name) manufactured by TOHO CHEMICAL INDUSTRY CO., LTD.]. These surfactants may be used alone, or two or more, preferably one to three of these surfactants may be mixed in appropriate proportions and then used.

Examples of a base material for the resin formulation include vinyl chloride polymers, and polyurethane . To the base material, if necessary, a plasticizer such as phthalate (e.g., dimethyl phthalate, dioctyl phthalate, etc.), adipate, stearic acid or the like may be added. The resin formulation is prepared by kneading the compound of the present invention into the base material using a conventional kneader, followed by molding such as injection molding, extrusion molding, press molding or the like. The resulting resin formulation may be formed into the shape of a plate, a film, a tape, a net, a string or the like via a further step of molding, cutting, or the like, if necessary. These resin formulations may be used, for example, the form of an animal collar, an animal ear tag, a sheet, a lead, or a horticultural post.

Examples of a base material of the poison bait include cereal powder, vegetable oil, sugar, and crystalline cellulose. To the base material, if necessary, an antioxidant such as dibutylhydroxytoluene or nordihydroguaiaretic acid, a preservative such as dehydroacetic acid, an agent for preventing children or pets from erroneously eating such as hot pepper powder, a pest-attractive perfume such as cheese perfume, onion perfume or peanut oil or the like may be added.

In addition, a binder, a dispersant, a colorant, a

stabilizer and the like, specifically, casein, gelatin, saccharides (e.g., starch, gum arabic, cellulose derivatives, alginic acid, etc.), lignin derivatives, bentonite, synthetic water-soluble polymers (e.g., polyvinyl alcohol, polyvinyl pyrrolidone, polyacrylic acid, etc.), PAP (acid isopropyl phosphate), BHT (2, 6-di-tert- butyl-4-methylphenol) , BHA (a mixture of 2-tert-butyl-4- methoxyphenol and 3-tert-butyl-4-methoxyphenol) , other substances described in Code of Federal Regulation Title 40 p.180, USA can be used as pharmaceutical auxiliary agents for preparing the pesticidal composition of the present invention.

The pesticidal composition of the present invention can comprise the compound of the present invention in combination with another pesticidal active ingredient, such as an insecticide (e.g., pyrethroid insecticide, organic phosphorus insecticide, carbamate insecticide, neonicotinoid insecticide, nerve sodium channel blocker, insecticidal macrocyclic lactone, γ-amino butyric acid (GABA) antagonisy, calcium channel activater, urea insecticide, insect hormone mimic, natural insecticide, etc.), an acaricide, a machine oil, a nematocide, a herbicide, a phytohormone agent, a plant growth regulator, a fungicide (e.g., copper fungicide, organic chlorine fungicide, organic sulfur fungicide, phenol fungicide,

etc.), a synergist, an attractant, a repellent, a crop injury-reducing agent, a pigment, a fertilizer, an animal feed (e.g., feed for livestock such as cows, pigs and chickens, feed for pet animals such as dogs and cats, feed for cultured fish such as young yellowtail and sea bream, etc.), an animal drug (e.g., a drug for treatment or prevention of disease of livestock, pet animals and cultured fish), a nutritional supplement for animals, or the like.

The pesticidal composition of the present invention contains usually 0.1 to 80% by weight, preferably 1 to 20% by weight of the compound of the present invention. Specifically, when the pesticidal composition of the present invention is in the form of an emulsifiable concentrate, a liquid formulation or a wettable powder (e.g., a wetabble granule), it contains usually 1 to 80% by weight, preferably 1 to 20% by weight of the compound of the present invention. When the pesticidal composition of the present invention is in the form of an emulsifiable concentrate or a dust, it cntains usually 0.1 to 50% by weight, preferably 0.1 to 20% by weight of the compound of the present invention. When the pesticidal composition of the present invention is in the form of a granule, it contains usually 1 to 50% by weight, preferably 1 to 20% by weight of the compound of the present invention.

Another pesticidal active ingredient (e.g., insecticide, herbicide, an acaricide, fungicide, etc.) may be present in usually 0.1 to 80% by weight, preferably 1 to 20% by weight in the pesticidal composition of the present invention.

The content of additives other than the pesticidal active ingredient described above in the pesticidal composition of the present invention is usually 0.001 to 99.9% by weight, preferably 1 to 99% by weight, although it is varied depending on the kind and content of the pesticidal active ingredient, the form of the pesticidal composition and the like. Specifically, the content of a surfactant in the pesticidal composition of the present invention is usually 1 to 20% by weight, preferably 1 to 15% by weight. The content of a fluidizing aid in the pesticidal composition of the present invention is usually 1 to 20% by weight. The content of a carrier in the pesticidal composition of the present invention is usually 1 to 90% by weight, preferably 1 to 70% by weight.

When the pesticidal composition of the present invention is in the form of an emulsifiable concentrate or a wettable powder (e.g., a wetabble granule), it is preferably diluted with water or the like as appropriate (e.g., 100 to 5,000 times) and then sprayed.

The compound of the present invention can be used as

an insecticide for crop lands such as cultivated lands, paddy fields, lawns and orchards, or non-crop lands. The compound of the present invention can control pests in crop lands and the like where "crop plants" listed below are cultivated without causing adverse effects on the "crop plants", in some cases.

Specific examples of the "crop plant" are listed below.

Agricultural crops: corn, rice, wheat, barley, rye, oat, sorghum, cotton, soybean, peanut, sarrazin, sugar beet, rapeseed, sunflower, sugar cane, tobacco, etc.;

Vegetables: Solanaceae vegetables (eggplant, tomato, green pepper, hot pepper, potato etc.), Cucurbitaceae vegetables (cucumber, pumpkin, zucchini, watermelon, melon etc.), Cruciferae vegetables (Japanese radish, turnip, horseradish, kohlrabi, Chinese cabbage, cabbage, brown mustard, broccoli, cauliflower etc.), Compositae vegetables (burdock, garland chrysanthemum, artichoke, lettuce etc.), Liliaceae vegetables (Welsh onion, onion, garlic, asparagus etc.), Umbelliferae vegetables (carrot, parsley, celery, parsnip etc.), Chenopodiaceae vegetables (spinach, Swiss chard etc.), Labiatae vegetables (Japanese basil, mint, basil etc.), strawberry, sweat potato, yam, aroid, etc.;

Fruit trees: pomaceous fruits (apple, common pear, Japanese pear, Chinese quince, quince etc.), stone fleshy

fruits (peach, plum, nectarine, Japanese plum, cherry, apricot, prune etc.)/ citrus plants (Satsuma mandarin, orange, lemon, lime, grapefruit etc.), nuts (chestnut, walnut, hazel nut, almond, pistachio, cashew nut, macadamia nut etc.), berry fruits (blueberry, cranberry, blackberry, raspberry etc.), grape, persimmon, olive, loquat, banana, coffee, date, coconut palm, oil palm, etc.;

Trees other than fruit trees: tea, mulberry, street trees (ash tree, birch, dogwood, eucalyptus, ginkgo, lilac, maple tree, oak, poplar, cercis, Chinese sweet gum, plane tree, zelkova, Japanese arborvitae, fir tree, Japanese hemlock, needle juniper, pine, spruce, yew, elm, horse- chestnut etc.), sweet viburnum, Podocarpus macrophyllus, Japanese cedar, Japanese cypress, croton, spindle tree, Chainese howthorn, etc.

Lawn: zoysia (Japanese lawn grass, mascarene grass, etc.), Bermuda grass (Cynodon dactylon, etc.), bent grass (creeping bent grass, Agrostis stolonifera, Agrostis tenuis, etc.), bluegrass (Kentucky bluegrass, rough bluegrass, etc.), fescue (tall fescue, chewing fescue, creeping fescue, etc.), ryegrass (darnel, perennial ryegrass, etc.), cocksfoot, timothy grass, etc.;

Oil crops: oil palm, Barbados nut, etc.;

Others: flowers (rose, carnation, chrysanthemum, ξustoma grandiflorum Shinners (prairie gentian) ,

gypsophila, gerbera, pot marigold, salvia, petunia, verbena, tulip, aster, gentian, lily, pansy, cyclamen, orchid, lily of the valley, lavender, stock, ornamental kale, primula, poinsttia, gladiolus, cattleya, daisy, verbena, cymbidium, begonia, etc.), foliage plant; etc..

The above-described crop plants include those to which resistance to an HPPD inhibitor such as isoxaflutole, an ALS inhibitor such as imazethapyr or thifensulfuron-methyl , an EPSP synthesizing enzyme inhibitor such as glyphosate, a glutamine synthesizing enzyme inhibitor such as glufosinate, an acetyl CoA carboxylase inhibitor such as sethoxydim, a PPO inhibitor such as flumioxazin, or an herbicide such as bromoxynil, dicamba or 2, 4-D, has been imparted by a classical breeding method or a genetic engineering technique.

Examples of the crop plant to which the resistance has been imparted by a classical breeding method include rape, whieat, sunflower, rice and corn having resistance to imidazolinone herbicides such as imazethapyr, which are commercially available under the trade name of Clearfield (registered trademark) ; soybean having resistance to sulfonylurea ALS inhibitor herbicides such as thifensulfuron-methyl, which is commercially available under the trade name of STS soybean; and crop plants having resistance to acetyl CoA carboxylase inhibitors such as

trione oxime hebicides and aryloxyphenoxypropionic acid herbicides, an example of which is SR corn. For example, a crop plant to which resistance to an acetyl CoA carboxylase inhibitor has been imparted is found in Proc . Natl. Acad. Sci. USA, 1990, vol. 87, p.7175-7179. In addition, a mutant acetyl CoA carboxylase which is resistant to an acetyl CoA carboxylase inhibitor is described in Weed Science, vol. 53, p.728-746, 2005. When a gene encoding the mutant acetyl CoA carboxylase is introduced into a crop plant by a genetic engineering technique or when a mutation related to impartation of the acetyl CoA carboxylase resistance is introduced into a gene encoding acetyl CoA carboxylase of a crop plant, a crop plant resistant to an acetyl CoA carboxylase inhibitor can be produced. Further, nucleic acids for introduction of a base substitution mutation can be introduced into the cells of a crop plant by chimeraplasty (see, Gura T. 1999, Repairing the Genome's Spelling Mistakes, Science 285: 316-318) to induce a site- directed amino acid substitution mutation in the gene which is targeted by an acetyl CoA carboxylase inhibitor or herbicide of the crop plant, and thereby a crop plant resistant to an acetyl CoA carboxylase inhibitor or herbicide can be produced.

Examples of the crop plant to which the resistance has been imparted by a genetic engineering technique include

corn, soybean, cotton, rape and sugar beet cultivars which are resistant to glyphosate, which are commercially available under the trade names of RoundupReady™ (registered trademark) , AgrisureGT, and the like. Other examples of the crop plant to which the resistance has been imparted by a genetic engineering technique include corn, soybean, cotton and rape cultivars which are resistant to glufosinate, which are commercially available under the trade name of LibertyLink™ and the like. In addition, a genetically engineered cotton cultivar having resisitance to bromoxynil is commarcially available under the trade name of BXN.

The above-described crop plants include those to which ability to produce an insecticidal toxin, for example a selective toxin which is known to be produced by Bacillus, has been imparted by a genetic engineering technique.

Examples of the insecticidal toxin which is produced by such a genetically engineered plant include insecticidal proteins derived from Bacillus cereus and Bacillus popilliae; δ-endotoxins derived from Bacillus thuringiensis, such as CryIAb, CryIAc, CrylF, CrylFa2 , Cry2Ab, Cry3A, Cry3Bbl and Cry9C; insecticidal proteins derived from Bacillus thuringiensis, such as VIP 1, VIP 2, VIP 3 and VIP 3A; insecticidal proteins derived from nematodes _/ toxins produced by animals such as scorpion

toxins, spider toxins, bee toxins and insect-specific nerve toxins; fungal toxins,- plant lectin; agglutinin; protease inhibitors such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin, and papain inhibitors; ribosome-inactivating proteins (RIP) such as ricin, corn- RIP, abrin, saporin, and briodin; steroid metabolizing enzymes such as 3-hydroxysteroid oxidase, ecdysteroid-UDP- glucosyltransferase, and cholesterol oxidase; ecdysone inhibitors; HMG-CoA reductase; ion channel inhibitors such as sodium channel inhibitors and calcium channel inhibitors; juvenile hormone esterase; diuretic hormone receptors; stilbene synthase; bibenzyl synthase; chitinase; and glucanase .

The insecticidal toxin which is produced by such a genetically engineered plant also includes hybrid toxins of different insecticidal proteins, for example, insecticidal proteins such as δ-endotoxins such as CryIAb, CryIAc, CrylF, CrylFa2 , Cry2Ab, Cry3A, Cry3Ebl and Cry9C, VIP 1, VIP 2, VIP 3 and VIP 3A, and toxins in which a part of amino acids constituting an insecticidal protein is deleted or modified. The hybrid toxin is made by combining different domains of the insecticidal proteins by a genetic engineering technique. An example of the toxin in which a part of amino acids constituting an insecticidal protein is deleted includes CrylAb in which a part of amino acids is

deleted. An example of the toxin in which a part of amino acids constituting an insecticidal protein is modified includes a toxin in which one or more of amino acids of a naturally occurring toxin are substituted.

The insecticidal toxin and the genetically engineered crop plant having the ability to produce the insecticidal toxin are described, for example, in EP-A-O 374 753, WO 93/07278, WO 95/34656, EP-A-O 427 529, EP-A-451878, WO 03/052073, and the like.

The genetically engineered crop plant having the ability to produce the insecticidal toxin particularly has resistance to attack by a coleopteran pest, dipteran pest or a lepidopteran pest .

Genetically engineered plants which have one or more pest-resistance genes and thereby produce one or more insecticidal toxins are also known, and some of them are commercially available. Examples of such genetically engineered plants include YieldGard™ (a corn cultivar expressing CrylAb toxin) , YieldGard Rootworm™ (a corn cultivar expressing Cry3Bbl toxin) , YieldGard Plus™ (a corn cultivar expressing CrylAb and Cry3Bbl toxins) , Herculex I™ (a corn cultivar expressing CrylFa2 toxin and phosphinothricin N-acetyltransferase (PAT) for imparting resistance to gluphosinate) , NuCOTN33B™ (a cotton cultivar expressing CrylAc toxin) , Bollgard I™ (a cotton cultivar

expressing CrylAc toxin) , Bollgard II™ (a cotton cultivar expressing CrylAc and Cry2Ab toxins) , VIPCOT™ (a cotton cultivar expressing VIP toxin) , NewLeaf™ (a potato cultivar expressing Cry3A toxin) , NatureGard Agrisure GT Advantage™ (GA21 glyphosate-resistance character) , Agrisure CB Advantage™ (BtIl corn borer (CB) character) , Protecta™, and the like.

The above-described crop plants include those to which ability to produce an anti -pathogen substance has been imparted by a genetic engineering technique.

Examples of the anti-pathogen substance includes PR proteins (PRPs described in EP-A-O 392 225) ; ion channel inhibitors such as sodium channel inhibitors, and calcium channel inhibitors (e.g. KPl, KP4 , KP6 toxins etc. produced by viruses) ; stilbene synthase; bibenzyl synthase; chitinase; glucanase; substances produced by microorganisms such as peptide antibiotics, heterocycle-containing antibiotics, and protein factors involved in plant disease- resistance (described in WO 03/000906) ; and the like. Such anti-pathogen substances and genetically engineered plants which produce the anti-pathogen substances are described in EP-A-O 392 225, WO 05/33818, EP-A-O 353 191, and the like.

The above-described crop plants include those to which a beneficial character such as a modified oil component or an enhanced amino acid content has been imparted by a

genetic engineering technique. Examples of such crop paints include VISTIVE™ (low linolenic soybean which has a reduced content of linolenic acid) , and high-lysine (high- oil) corn (corn which has an increased content of lysine or oil) .

Furthermore, the above-described crop plants include stacked plants which have a combination of two or more of beneficial characters such as the above-described classical harbicide-resistant character, or a herbicide-resistace gene, a pest-resistance gene, an anti-pathogen substance- producing gene, a modified oil component, and an enhanced amino acid content .

When the compound of the present invention is used for the herbicide-resistant crop plant as described above, the plant is treated with sequentially or a mixture of the compound of the present invention and the herbicide (e.g., glyphosate or a salt thereof, glufosinate or a salt thereof, dicamba or a salt thereof, imazethapyr or a salt thereof, isoxaflutole, etc.) to which the plant is resistant, and thereby comprehensive weed control can be attained.

Examples of active ingredients of insecticides, acaricides, nematocides, fungicides, herbicides, phytohormone agents, plant growth regulators, synergists and crop injury-reducing agents (hereinafter, referred to

as "the active ingredient group X") which can be used in combination with the compound of the present invention are listed below.

Examples of active ingredients of the insecticides include :

(1) organic phosphorus compounds: acephate, aluminum phosphide, butathiofos, cadusafos, chlorethoxyfos, chlorfenvinphos, chlorpyrifos, chlorpyrifos-methyl, cyanophos (CYAP), diazinon, DCIP

(dichlorodiisopropyl ether) , dichlofenthion (ECP) , dichlorvos (DDVP), dimethoate, dimethylvinphos , disulfoton, EPN, ethion, ethoprophos, etrimfos, fenthion (MPP) , fenitrothion (MEP) , fosthiazate, formothion, hydrogen phosphide, isofenphos, isoxathion, malathion, mesulfenfos, methidathion (DMTP) , monocrotophos , naled (BRP) , oxydeprofos (ESP) , parathion, phosalone, phosmet (PMP) , pirimiphos-methyl , pyridafenthion, quinalphos, phenthoate

(PAP), profenofos, propaphos, prothiofos, pyraclorfos, salithion, sulprofos, tebupirimfos, temephos, tetrachlorvinphos, terbufos, thiometon, trichlorphon (DEP) , vamidothion, phorate, cadusafos, and the like;

(2) carbamate compounds: alanycarb, bendiocarb, benfuracarb, BPMC, carbaryl, carbofuran, carbosulfan, cloethocarb, ethiofencarb, fenobucarb, fenothiocarb, fenoxycarb, furathiocarb,

isoprocarb (MIPC), metolcarb, methotnyl, methiocarb, NAC, oxamyl, pirimicarb, propoxur (PHC), XMC, thiodicarb, xylylcarb, aldicarb, and the like;

(3) synthetic pyrethroid compounds: acrinathrin, allethrin, beta-cyfluthrin, bifenthrin, cycloprothrin, cyfluthrin, cyhalothrin, cypermethrin, empenthrin, deltamethrin, esfenvalerate, ethofenprox, fenpropathrin, fenvalerate, flucythrinate, flufenoprox, flumethrin, fluvalinate, halfenprox, imiprothrin, permethrin, prallethrin, pyrethrins, resmethrin, sigma- cypermethrin, silafluofen, tefluthrin, tralomethrin, transfluthrin, tetramethrin, phenothrin, cyphenothrin, alpha-cypermethrin, zeta-cypermethrin, lambda-cyhalothrin, gamma-cyhalothrin, furamethrin, tau-fluvalinate, metofluthrin, 2 , 3 , 5, 6-tetrafluoro-4-methylbenzyl 2,2- dimethyl-3 - (1-propenyl) cyclopropanecarboxylate, 2,3,5,6- tetrafluoro-4- (methoxymethyl) benzyl 2 , 2-dimethyl-3- (2- methyl-1-propenyl) cyclopropanecarboxylate, 2,3,5,6- tetrafluoro-4- (methoxymethyl) benzyl 2 , 2-dimethyl-3- (2- cyano-1-propenyl) cyclopropanecarboxylate, 2,3,5,6- tetrafluoro-4- (methoxymethyl) benzyl 2,2,3,3- tetramethylcyclopropanecarboxylate, and the like;

(4) nereistoxin compounds: cartap, bensultap, thiocyclam, monosultap, bisultap, and the like;

(5) neonicotinoid compounds: imidacloprid, nitenpyram, acetamiprid, thiamethoxam, thiacloprid, dinotefuran, clothianidin, and the like;

(6) benzoylurea compounds: chlorfluazuron, bistrifluron, diafenthiuron, diflubenzuron, fluazuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron, triflumuron, triazuron, and the like;

(7) phenylpyrazole compounds: acetoprole, ethiprole, fipronil, vaniliprole, pyriprole, pyrafluprole, and the like;

(8) Bt toxin insecticides: live spores derived from and crystal toxins produced from Bacillus thuringiesis and a mixture thereof;

(9) hydrazine compounds: chromafenozide, halofenozide, methoxyfenozide, tebufenozide, and the like;

(10) organic chlorine compounds: aldrin, dieldrin, dienochlor, endosulfan, methoxychlor, and the like;

(11) natural insecticides: machine oil, nicotine sulfate, and the like;

(12) other insecticides: avermectin, bromopropylate, buprofezin, chlorphenapyr, cyromazine, D-D (1, 3-dichloropropene) , emamectin-benzoate,

fenazaquin, flupyrazofos, hydroprene, methoprene, indoxacarb, metoxadiazone, milbemycin-A, pymetrozine, pyridalyl, pyriproxyfen, spinosad, sulfluramid, tolfenpyrad, triazamate, flubendiamide, lepimectin, arsenic acid, benclothiaz, calcium cyanamide, calcium polysulfide, chlordane, DDT, DSP, flufenerim, flonicamid, flurimfen, formetanate, metham-ammonium, metam-sodium, methyl bromide, potassium oleate, protrifenbute, spiromesifen, sulfur, metaflumizone, spirotetramat , pyrifluquinazone, spinetoram, chlorantraniliprole, tralopyril, a compound represented by the following formula (A) :

wherein X ^al represents a methyl group, a chlorine atom, a bromine atom or a fluorine atom, X ^a2 represents a fluorine atom, a chlorine atom, a bromine atom, a C1-C4 haloalkyl grop or a C1-C4 haloalkoxy group, X ^a3 represents a fluorine atom, a chlorine atom or a bromine atom, X ^a4 represents an optionally substituted C1-C4 alkyl group, an optionally substituted C3-C4 alkenyl group , an optionally substituted C3-C4 alkynyl group, an optionally substituted C3-C5 cycloalkylalkyl group or a hydrogen atom, X ^a5 represents a

hydrogen atom or a methyl group, X ^a6 represents a hydrogen atom, a fluorine atom or a chlorine atom, and X ^a7 represents a hydrogen atom, a fluorine atom or a chlorine atom; a compound represented by the following formula (B) :

wherein X ^bl represents a X ^b2 -NH-C(=O) group, a X ^b2 -C (=0) -NH- CH ₂ group, a X ^b3 -S(O) group, an optionally substituted pyrrol-1-yl group, an optionally substituted imidazol-1-yl group, an optionally substituted pyrazol-1-yl group, or an optionally substituted 1, 2 , 4-triazol-l-yl group, X ^b2 represents an optionally substituted C1-C4 haloalkyl group, such as a 2 , 2 , 2-trifluoroethyl group, or an optionally substituted C3-C6 cycloalkyl group, such as a cyclopropyl group, X ^b3 represents an optionally substituted C1-C4 alkyl group, such as a methyl group, and X ^b4 represents a hydrogen atom, a cyano group or a methyl group; a compound represented by the following formula (C) :

wherein X ^cl represents an optionally substituted C1-C4 alkyl group, such as a 3 , 3 , 3-trifluoropropyl group, an optionally substituted C1-C4 alkoxy group, such as a 2,2,2- trichloroethoxy group, an optionally substituted phenyl group, such as a 4-cyanophenyl group, or an optionally substituted pyridyl group, such as a 2-chloro-3-pyridyl group, X ^c2 represents a methyl group or a trifluoromethylthio group, and X ⁰³ represents a methyl group or a halogen atom; and the like.

Examples of active ingredients of the acaricides include acequinocyl, amitraz, benzoximate, bifenazate, bromopropylate, chinomethionate, chlorobenzilate, CPCBS (chlorfenson) , clofentezine, cyflumetofen, kelthane (dicofol) , etoxazole, fenbutatin oxide, fenothiocarb, fenpyroximate, fluacrypyrim, fluproxyfen, hexythiazox, propargite (BPPS), polynactins, pyridaben, pyrimidifen, tebufenpyrad, tetradifon, spirodiclofen, spiromesifen, spirotetramat , amidoflumet, cyenopyrafen, and the like.

Examples of active ingredients of the nematicides include DCIP, fosthiazate, levamisol hydrochloride, methylisothiocyanate, morantel tartarate, imicyafos .

Examples of active ingredients of the fungicides include azole fungicidal compounds such as propiconazole, prothioconazole, triadimenol, prochloraz, penconazόle, tebuconazole, flusilazole, diniconazole, bromuconazole,

epoxiconazole, difenoconazole, cyproconazole, metconazole, triflumizole, tetraconazole, myclobutanil, fenbuconazole, hexaconazole, fluquinconazole, triticonazole, bitertanol, imazalil, and flutriafol; cyclic amine fungicidal compouds such as fenpropimorph, tridemorph, and fenpropidin; benzimidazole fungicidal compounds such as carbendezim, benomyl, thiabendazole, and thiophanate-methyl ; procymidone, cyprodinil, pyrimethanil, diethofencarb, thiuram, fluazinam, mancozeb, iprodione, vinclozolin, chlorothalonil, captan, mepanipyrim, fenpiclonil, fludioxonil, dichlofluanid, folpet, kresoxim-methyl, azoxystrobin, trifloxystrobin, fluoxastrobin, picoxystrobin, pyraclostrobin, dimoxystrobin, spiroxamine, quinoxyfen, fenhexamid, famoxadone, fenamidone, zoxamide, ethaboxam, amisulbrom, iprovalicarb, benthiavalicarb, cyazofamid, mandipropamid, boscalid, metrafenone, fluopiran, bixafen, cyflufenamid, and proquinazid.

Examples of active ingredients of the herbicides and the phytohormone agents include:

(1) phenoxyfatty acid herbicidal compounds such as 2,4-PA, MCP, MCPB, phenothiol, mecoprop, fluroxypyr, triclopyr, clomeprop, and naproanilide;

(2) benzoic acid herbicidal compounds such as 2,3,6- TBA, dicamba, clopyralid, picloram, aminopyralid,

quinclorac, and quinmerac;

(3) urea herbicidal compounds such as diuron, linuron, chlortoluron, isoproturon, fluometuron, isouron, tebuthiuron, methabenzthiazuron, cumyluron, daimuron, and methyl-daimuron;

(4) triazine herbicidal compounds such as atrazine, ametoryn, cyanazine, simazine, propazine, simetryn, dimethametryn, prometryn, metribuzin, and triaziflam;

(5) bipyridinium herbicidal compounds such as paraquat , and diquat ;

(6) hydroxybenzonitrile herbicidal compounds such as bromoxynil and ioxynil;

(7) dinitroaniline herbicidal compounds such as pendimethalin, prodiamine, and trifluralin;

(8) organic phosphorus herbicidal compounds such as amiprofos-methyl, butamifos, bensulide, piperophos, anilofos, glyphosate, glufosinate, and bialaphos;

(9) carbamate herbicidal compounds such as di-allate, tri-allate, EPTC, butylate, benthiocarb, esprocarb, molinate, dimepiperate, swep, chlorpropham, phenmedipham, phenisopham, pyributicarb, and asulam;

(10) acid amide herbicidal compounds such as propanil, propyzamide, bromobutide, and etobenzanid;

(11) chloroacetanilide herbicidal compounds such as acetochlor, alachlor, butachlor, dimethenamid, propachlor,

metazachlor, metolachlor, pretilachlor, thenylchlor, and pethoxamid;

(12) diphenylether herbicidal compounds such as acifluorfen-sodium, bifenox, oxyfluorfen, lactofen, fomesafen, chlomethoxynil, and aclonifen;

(13) cyclic imide herbicidal compounds such as oxadiazon, cinidon-ethyl , carfentrazone-ethyl, surfentrazone, flumiclorac-pentyl , flumioxazin, pyraflufen- ethyl, oxadiargyl, pentoxazone, fluthiacet-methyl, butafenacil, and benzfendizone;

(14) pyrazole herbicidal compounds such as benzofenap, pyrazolate, pyrazoxyfen, topramezone, and pyrasulfotole;

(15) triketone herbicidal compounds such as isoxaflutole, benzobicyclon, sulcotrione, mesotrione, tembotrione, and tefuryltrione;

(16) aryloxyphenoxypropionic acid herbicidal compounds such as clodinafop-propargyl, cyhalofop-butyl, diclofop- methyl , fenoxaprop-ethyl, fluazifop-butyl, haloxyfop- methyl , and quizalofop-ethyl ;

(17) trioneoxime herbicidal compounds such as alloxydim-sodium, sethoxydim, butroxydim, clethodim, cloproxydim, cycloxydim, tepraloxydim, tralkoxydim, and profoxydim;

(18) sulfonylurea herbicidal compounds such as chlorsulfuron, sulfometuron-methyl, metsulfuron-methyl,

chlorimuron-ethyl, tribenuron-methyl, triasulfuron, bensulfuron-methyl, thifensulfuron-methyl, pyrazosulfuron- ethyl, primisulfuron-methyl , nicosulfuron, amidosulfuron, cinosulfuron, imazosulfuron, rimsulfuron, halosulfuron- methyl, prosulfuron, ethametsulfuron-methyl, triflusulfuron-methyl, flazasulfuron, cyclosulfamuron, flupyrsulfuron, sulfosulfuron, azimsulfuron, ethoxysulfuron, oxasulfuron, iodosulfuron-methyl-sodium, foramsulfuron, mesosulfuron-methyl, trifloxysulfuron, tritosulfuron, orthosulfamuron, flucetosulfuron, and 1- (2- chloro-6-propylimidazo [1, 2 -a] pyridazin-3-ylsulfonyl) -3- (4 , 6-dimethoxypyrimidin-2-yl) urea;

(19) imidazolinone herbicidal compounds such as imazamethabenz-methyl, imazamethapyr, imazamox, imazapyr, imazaquin, and imazethapyr;

(20) sulfonamide herbicidal compounds such as flumetsulam, metosulam, diclosulam, florasulam, cloransulam-methyl, penoxsulam, and pyroxsulam;

(21) pyrimidinyloxybenzoic acid herbicidal compounds such as pyrithiobac-sodium, bispyribac-sodium, pyriminobac- methyl, pyribenzoxim, and pyriftalid; and

(22) other herbicidal compounds such as bentazon, bromacil, terbacil, chlorthiamid, isoxaben, dinoseb, amitrole, cinmethylin, tridiphane, dalapon, diflufenzopyr- sodium, dithiopyr, thiazopyr, flucarbazone-sodium,

propoxycarbazone-sodium, mefenacet, flufenacet, fentrazamide, cafenstrole, indanofan, oxaziclomefone, benfuresate, ACN, pyridate, chloridazon, norflurazon, flurtamone, diflufenican, picolinafen, beflubutamid, clomazone, amicarbazone, pinoxaden, and thiencarbazone- methyl .

Examples of active ingredients of the plant growth regulators include hymexazol, paclobutrazol, uniconazole-P, inabenfide, prohexadione-calcium, aviglycine, 1- naphthylacetamide, abscisic acid, indolebutyric acid, ethychlozate ethyl, ethephon, cloxyfonac, chlormequat, dichlorprop, gibberellin, prohydrojasmon, benzylaminopurine, forchlorfenuron, maleic hydrazide, calcium peroxide, mepiquat chloride) and 4 -CPA (4- chlorophenoxyacetic acid) .

Examples of active ingredients of the synergists include piperonyl butoxide, sesamex, sulfoxide, N- (2- ethylhexyl) -8,9, 10-trinorborn-5-ene-2 , 3-dicarboximide (MGK 264) , N-declyimidazole, WARF-antiresistant , TBPT, TPP, IBP, PSCP, methyl iodide (CH3I) , t-phenylbutenone, diethylmaleate, DMC, FDMC, ETP, and ETN.

Examples of active ingredients of the crop injury- reducing agents include benoxacor, cloquintocet-mexyl , cyometrinil, daimuron, dichlormid, fenchlorazole-ethyl, fenclorim, flurazole, fluxofenim, furilazole, mefenpyr-

diethyl, MG191, oxabetrinil, allidochlor, isoxadifen-ethyl, cyprosulfamide, fluxofenim, and 1, 8-naphthalic anhydride.

Examples of pests on which the compound of the present invention exhibits a controlling effect include arthropod pests such as harmful insects and harmful mites, and more specifically, the following pets.

Hemiptera :

Planthoppers (Delphacidae) such as small brown planthopper {Laodelphax striatellus) , brown rice planthopper {Nilaparvata lugens) , and white-backed rice planthopper {Sogatella furcifera) ; leafhoppers (Deltocephalidae) such as green rice leafhopper {Nephotettix cincticeps) , green rice leafhopper {Nephotettix virescens) , and tea green leafhopper {Empoasca onukii) ; aphids (Aphididae) such as cotton aphid (Aphis gossypii) , green peach aphid {Myzus persicae) , cabbage aphid (Brevicoryne brassicae) , piraea aphid {Aphis spiraecola) , potato aphid {Macrosiphum euphorbiae) , foxglove aphid {Aulacorthum solani) , oat bird-cherry aphid {Rhopalosiphum padi) , tropical citrus aphid {Toxoptera citricidus) , and mealy plum aphid (Hyalopterus pruni) ; stink bugs (Pentatomidae) such as green stink bug {Nezara antennata) , bean bug {Riptortus clavatus) , rice bug (Leptocorisa chinensis) , white spotted spined bug

{Eysarcoris parvus) , and stink bug {Halyomorpha mista) ; whiteflies (Aleyrodidae) such as greenhouse whitefly (Trialeurodes vaporariorum) , sweetpotato whitefly {Bemisia tabaci) , silverleaf whitefly {Bemisia argentifolH) , citrus whitefly {Dialeurodes citri) , and citrus spiny white fly (Aleurocanthus spiniferus) ; scales (Coccidae) such as Calfornia red scale {Aonidiella aurantii) , San Jose scale (Comstockaspis pemiciosa) , citrus north scale {Unaspis citri) , red wax scale (Ceroplastes rubens) , cottonycushion scale {Icerya purchasi) , Japanese mealybug {Planococcus kraunhiae) , Cosmstock mealybug {Pseudococcus longispinus) , and white peach scale (Pseudaulacaspis pentagona) ; lace bugs (Tingidae) ; cimices such as Cimex lectularius; psyllids (Psyllidae) ; etc.

Lepidoptera:

Pyralid moths (Pyralidae) such as rice stem borer {Chilo suppressalis) , yellow rice borer {Tryporyza incertulas) , rice leafroller {Cnaphalocrocis medinalis) , cotton leafroller (Notarcha derogata) , Indian meal moth {Plodia interpunctella) , oriental corn borer {Ostrinia furnacalis) , cabbage webworm {Hellula undalis) , and bluegrass webworm (Pediasia teterrellus) ; owlet moths (Noctuidae) such as common cutworm {Spodoptera litura) , beet armyworm {Spodoptera exigua) , armyworm {Pseudaletia separata) , cabbage armyworm {Mamestra brassicae) , black

cutworm {Agrotis ipsilon) , beet semi-looper {Plusia nigrisigna) , Thoricoplusia spp., Heliothis spp., and Helicoverpa spp.; white butterflies (Pieridae) such as common white (Pieris rapae) ; tortricid moths (Tortricidae) such as Adoxophyes spp., oriental fruit moth {Grapholita molesta) , soybean pod borer (Leguminivora glycinivorella) , azuki bean podworm {Matsumuraeses azukivora) , summer fruit tortrix {Adoxophyes orana fasciata) , smaller tea tortrix

(Adoxophyes honmai . ) , oriental tea tortrix {Homona magnanima) , apple tortrix {Archips fuscocupreanus) , and codling moth {Cydia pomonella) ; leafblotch miners

(Gracillariidae) such as tea leafroller {Caloptilia theivora) , and apple leafminer (Phyllonorycter ringoniella) ; Carposinidae such as peach fruit moth

(Carposina niponensis) ; lyonetiid moths (Lyonetiidae) such as Lyonetia spp.; tussock moths (Lymantriidae) such as Lymantria spp., and Euproctis spp.; yponomeutid moths

(Yponomeutidae) such as diamondback {Plutella xylostella) ; gelechiid moths (Gelechiidae) such as pink bollworm

(Pectinophora gossypiella) , and potato tubeworm

{Phthorimaea operculella) ; tiger moths and allies

(Arctiidae) such as fall webworm {Hyphantria cunea) ; tineid moths (Tineidae) such as casemaking clothes moth {Tinea translucens) , and webbing clothes moth {Tineola b±sselliella) ; etc.

Thysanoptera :

Thrips (Thripidae) such as yellow citrus thrips (Frankliniella occi.denta.lls), melon thrips (Thrips palml) , yellow tea thrips [Sclrtothrips dorsalis) , onion thrips {Thrips tahaci) , flower thrips (Frankliniella intonsa) , etc .

Diptera:

Culices such as common mosquito (Culβx pipiens pallens) , Cluex tritaeniorhynchus, and Cluex quinquefasciatus; Aedes spp . such as yellow fever mosquito (Aedes aegypti) , and Asian tiger mosquito (Aedes albopictus) ; Anopheles spp. such as Anopheles sinensis; chironomids (Chironomidae) ; house flies (Muscidae) such as Musca domestica, and Muscina stabulans; blow flies (Calliphoridae) ; flesh flies (Sarcophagidae) ; little house flies (Fanniidae) ; anthomyiid flies (Anthomyiidae) such as seedcorn fly (Delia platura) , and onion fly (Delia antigua) ; leafminer flies (Agromyzidae) such as rice leafminer (Agromyza oryzae) , little rice leafminer (Hydrellia griseola) , tomato leafminer (Liriomyza sativae) , legume leafminer (Liriomyza trifolii) , and garden pea leafminer (Chromatomyia horticola) ; gout flies (Chloropidae) such as rice stem maggot (Chlorops oryzae) ; fruit flies (Tephritidae) such as melon fly (Dacus cucurbitae) , and Meditteranean fruit fly (Ceratitis

capitata) ; Drosophilidae; humpbacked flies (Phoridae) such as Megaselia spiracularis; moth flies (Psychodidae) such as Clogmia albipunctata; Simuliidae; Tabanidae such as horsefly (Tabanus trigonus) ; stable flies, etc. Coleoptera:

Corn root worms {Diabrotica spp.) such as Western corn root worm {Diabrotica virgifera virgifera) , and Sourthem corn root worm {Diabrotica undecimpunctata howardi) ; scarabs (Scarabaeidae) such as cupreous chafer {Anomala cuprea) , soybean beetle {Anomala rufocuprea) , and Japanese beetle {Popillia japonica) ; weevils such as maize weevil

{Sitophilus zeamais) , rice water weevil {Lissorhoptrus ory∑ophilus) , azuki bean weevil {Callosobruchus chinensis) , rice curculio {Echinocnemus squameus) , boll weevil

{Anthonomus grandis) , and hunting billbug {Sphenophorus venatus) ; darkling beetles (Tenebrionidae) such as yellow mealworm {Tenebrio molitor) , and red flour beetle

{Tribolium castaneum) ; leaf beetles (Chrysomelidae) such as rice leaf beetle (Oulema oryzae) , cucurbit leaf beetle

{Aulacophora femoralis) , striped flea beetle {Phyllotreta striolata) , and Colorado potato beetle {Leptinotarsa decemlineata) ; dermestid beetles (Dermestidae) such as varied carper beetle {Anthrenus verbasci) , and hide beetle

{Dermestes maculates) ; deathwatch beetles (Anobiidae) such as cigarette beetle {Lasioderma serricorne) ; Epilachna such

as Twenty-eight-spotted ladybird {Epilachna vigintioctopunctata) ; bark beetles (Scolytidae) such as powder-post beetle (Lyctus brunneus) , and pine shoot beetle {Tomicus piniperda) ; false powder-post beetles (Bostrychidae) ; spider beetles (Ptinidae) ; longhorn beetles (Cerambycidae) such as white-spotted longicorn beetle {Anoplophora malasiaca) ; click beetles {Agriotes spp . ) ; Paederus fuscipens, etc.

Orthoptera :

Asiatic locust {Locusta migratoria) , African mole cricket {Gryllotalpa africana) , rice grasshopper {Oxya yezoensis) , rice grasshopper (Oxya japonica) , Gryllidae, etc .

Siphonaptera :

Cat flea (Ctenocephalides felis) , dog flea {Ctenocephalides canis) , human flea (Pulex irritans) , oriental rat flea {Xenopsylla cheopis) , etc.

Anoplura :

Human body louse (Pediculus humanus corporis) , crab louse {Phthirus pubis) , short-nosed cattle louse (Haematopinus eurysternus) , sheep louse {Damalinia ovis) , hog louse {Haematopinus suis) , etc.

Hymenoptera :

Ants (Formicidae) such as pharaoh ant {Monomorium pharaonis) , negro ant {Formica fusca japonica) , black house

ant {Ochetellus glaber) , Pristomyrmex pungens, Pheidole noda, leaf-cutting ant {Acromyrmex spp . ) , and fire ant (Solenopsis spp.); hornets (Vespidae) ; bethylid wasps (Betylidae) ; sawflies (Tenthredinidae) such as cabbage sawfly (Athalia rosae) , and Athalia japonica, etc.

Blattodea:

German cockroach [Blattella germanica) , smokybrown cockroach {Perϊplaneta fuliginosa) , American cockroach (Periplaneta americana) , Periplaneta brunnea, oriental cockroach {Blatta orientalis) ; Isoptera :

Termites such as Japanese subterranean termite (.Reticulitermes speratus) , Formosan subterranean termite {Coptotermes formosanus) , western drywood termite {Incisitermes minor), Daikoku drywood termite ( Cryptotermes domest±cus) , Odontotermes formosanus, Neotermes koshunensis, Glyptotermes satsumensis, Glyptotermes nakajimai, Glyptotermes fuscus, Glyptotermes kodamai, Glyptotermes kushimensis, Japanese dampwood termite {Hodotermopsis japonica) , Coptotermes guangzhoensis, Reticulitermes miyatakei, eastern subterranean termite (Reticulitermes flavipes amamianus) , Reticulitermes sp. , Nasutitermes takasagoesis, Pericapritermes nitobei , Sinocapritermes mushae, Reticuliterumes flavipes, Reticulitermes hesperus, Reticulitermes virginicus,

Reticulitermes tibialis, Heterotermes aureus, and Zootermopsis nevadensis, etc.

Acarina:

Spider mites (Tetranychidae) such as two-spotted spider mite {Tetranychus urticae) , Kanzawa spider mite {Tetranychus kanzawai) , citrus red mite (Panonychus citri) , European red mite {Panonychus ulmi) , and Oligonychus spp . ; eriophyid mites (Eriophyidae) such as pink citrus rust mite (Aculops pelekassi) , Phyllocoptruta citri, tomato rust mite {Aculops lycopersici) , purple tea mite {Calacarus carinatus) , pink tea rust mite {Acaphylla theavagran) , Eriophyes chibaensis, and apple rust mite (Aculus schlechtendali) ; tarosonemid mites (Tarsonemidae) such as broad mite {Polyphagotarsonemus latus) ; false spider mites (Tenuipalpidae) such as Brevipalpus phoenicis; Tuckerellidae; ticks (Ixodidae) such as Haemaphysalis longicornis, Haemaphysalis flava, Dermacentor taiwanicus, American dog tick (Dermacentor variabilis) , Ixodes ovatus, Ixodes persulcatus, black leg tick (Ixodes scapularis) , lone star tick (Amblyomma americanum) , Boophilus microplus, and Rhipicephalus sanguineus; Psoroptidae such as ear mite (Otodectes cynotis) ; itch mites (Sarcoptidae) such as Sarcoptes scabiei; folicle mites (Demodicidae) such as dog folicle mite (Demodex canis) ; acarid mites (Acaridae) such as mold mite (Tyrophagus putrescentiae) , and Tyrophagus

similis; house dust mites (Pyroglyphidae) such as Dermatophagoid.es farinae, and Dermatophagoid.es ptrenyssnus; cheyletide mites (Cheyletidae) such as Cheyletus eruditus, Cheyletus malaccensis, and Cheyletus moorei ; parasitoid mites (Dermanyssidae) such as tropical rat mite (Ornithonyssus bacoti) , northern fowl mite (Ornithonyssus sylviarum) , and poultry red mite {Dermanyssus gallinae) ; chiggers (Trombiculidae) such as Leptotrombidium akamushi; spiders (Araneae) such as Japanese foliage spider {Chiracanthium japonicum) , redback spider {Latrodectus hasseltii) , etc.

Chilopoda: house centipede {Thereuonema hilgendorfi) , Scolopendra subspinipes, etc.;

Diplopoda: garden millipede {Oxidus gracilis) , Nedyopus tambanus, etc.;

Isopoda: common pill bug (Armadillidium vulgare) , etc . ;

Gastropoda: Limax marginatus, Limax flavus, etc.

Nematoda :

Rice white-tip nematode {Aphelenchoides besseyi) , strawberry bud nematode (Nothotylenchus acris) , southern root-knot nematode (Meloidogyne incognita) , northern root- knot nematode {Meloidogyne hapla) , Javanese root-knot nematode {Meloidogyne javanica) , soybean cyst nematode {Heterodera glycines) , potato cyst nematode {Globodera

rostochiensis) , coffee root-lesion nematode {Pratylenchus coffeae) , California root-lesion nematode {Pratylenchus neglectus) , etc.

The pesticidal composition comprising the compound of the present invention or a salt thereof can be used in the field of livestock disease therapy and livestock industry, and also can be used for exterminating organisms and parasites inhabiting the inside and/or outside of the body of vertebrates such as human being, cow, sheep, goat, pig, poulty, dog, cat and fish, to sustain public health. Examples of such organisms and parasites include ticks (Ixodes spp . ) (e.g. Ixodes scapularis) , Boophilus spp. (e.g. Boophilus microplus) , Amblyomma spp., Hyalomma spp., Rhipicephalus spp. (e.g. Rhipicephalus sanguineus), Haemaphysalis spp. (e.g. Haemaphysalis longicornis) , dermacentor spp., Ornithodoros spp. (e.g. Ornithodoros moubata) , parasitoid mites (Dermahyssus gallinae) , northern fowl mite (Ornithonyssus sylviarum) , itch mites (Sarcoptes spp.) (e.g Sarcoptes scabiei) , Psoroptes spp., Chorioptes spp., folicle mites (Demodex spp.), chiggers (Eutrombicula spp.), Aedes spp. (e.g. Asian tiger mosquito (Aedes albopictus) ) , Anopheles spp., Culex spp., Culicodes spp., Musca spp., Hypoderma spp., Gasterophilus spp., Haematobia spp., Tabanus spp., Simulium spp., Triatoma spp., lice

(Phthiraptera) (e.g. Damalinia spp . , Linognathus spp . , Haematopinus spp.), fleas (Ctenocephalides spp.) (e.g. cat flea (Ctenocephalides felis) , Xenosylla spp.), pharaoh ant (Monomorium pharaonis) , and Nematoda [for example, trichostrongyle (e.g. Nippostrongylus brasiliensis, Trichostrongylus axei, and Trichostrongylus colubriformis) , trichina (e.g. Trichinella spiralis), Haemonchus contortus, Nematodirus (e.g. Nematodirus battus) , Ostertagia circumcincta, Cooperia spp. , Hymenolepis nana, and the like.

A pest controlling method comprising applying the compound of the present invention to a pest or a place where the pest inhabits also falls within the scope of the present invention.

For the method of controlling a pest of the present invention, the compound of the present invention or a salt thereof may be used as it is, and however, the compound of the present invention is usually formulated into the form of the pesticidal composition of the present invention as described above and then used. The method of controlling a pest of the present invention comprises, for example, applying the compound of the present invention or a salt thereof or the pesticidal composition of the present invention to a pest or a place where the pest inhabits by a

method same as to an application method for conventional pesticides, to allow the pest to contact with or ingest the compound of the present invention or a salt thereof or the pesticidal composition of the present invention.

Examples of the place where the pest inhabits include a paddy field, a dry field, a cultivated field, a tea field, a fruit orchard, a non-cultivated field, a house, a raising sesdling tray, a nursery box, nursery soil, a nursery mat, a water cluture medium in a hydroponic farm, and the like.

Examples of such an application method include spray treatment, soil treatment, seed treatment and water cluture medium treatment. In the present invention, the spray treatment includes foliage spraying and truck spraying, and specifically comprises treating the plant surface or a pest itself with an active ingredient (the compound of the present invention or a salt thereof) , to exert a controlling effect on a pest. The soil treatment comprises, for example, treating rhizosphere soil of a plant to be protected from damage such as eating by a pest with an active ingredient to control the pest directly, or allowing the active ingredient to permeate from the root and the like of the plant to inside of the plant to control the pest. Specific examples of the soil treatment include planting hole treatment (planting hole spraying, soil

incorporation after planting hole treatment) , plant foot treatment (plant foot spraying, soil incorporation at plant foot, plant foot drenching, plant foot treatment at a later seeding raising stage) , planting furrow treatment (planting furrow spraying, soil incorporation after planting furrow treatment) , planting row treatment (planting row spraying, soil incorporation after planting row treatment, planting row spraying at a growing stage) , planting row treatment at the time of sowing (planting row spraying at the time of sowing, soil incorporation after planting row treatment at the time of sowing) , broadcast treatment (overall soil surface spraying, soil incorporation after broadcast treatment) , other soil spraying treatment (foliar spraying of a granule at a growth stage, spraying under trunks or around main stems, soil surface spraying, soil surface incorporation, sowing hole spraying, furrow surface spraying, and spraying between plants) , other drenching treatment (soil drenching, drenching at a raising seedling stage, chemical injection treatment, plant foot drenching, chemical drip irrigation, chemigation) , nursery box treatment (nursery box surface spraying, drenching of nursery box) , nursery tray treatment (nursery tray spraying, nursery tray irrigation) , nursery bed treatment (nursery bed surface spraying, drenching of nursery bed, lowland nursery bed surface spraying, seedling immersion) ,

bed soil incorporation treatment (bed soil incorporation, presowing bed soil incorporation) _; and other treatments (ridging incorporation, plowing and fertilizing, surface soil incorporation, soil incorporation under canopy edge, planting position treatment, flower cluster treatment with a granule, paste fertilizer incorporation) . The seed treatment comprises, for example, treating the seeds, seed potatoes or bulbs of a crop plant to be protected from damage such as eating by a pest, or the vicinity thereof with an active ingredient to exert a controlling effect on the pest. Specific examples the seed treatment include spraying, smearing, immersion, impregnation, application, film coating and pellet coating. The water culture medium treatment comprises, for example, adding an active ingredient to a water culture medium or the like so as to allow the active ingredient to permeate from the root and the like of a crop plant to be protected from damage such as eating by a pest to inside of the plant, thereby the plant is protected from damage by the pest. Specific examples of the water culture medium treatment include water culture medium incorporation, and water culture medium interfusion.

The application amount of the pesticidal composition of the present invention in the above-described application method may be appropriately changed depending on an

application timing, an application place, a formulation form and the like, and it is usually 0.3 to 3,000 g, preferably 50 to 3,000 g of an active ingredient (the compound of the present invention or a salt thereof) per 1 hectare of soil where a plant is grown. When the pesticidal composition of the present invention is in the form of a wettable powder, it is preferred that it is diluted with water to 0.1 to 1,000 ppm, preferably from 10 to 500 ppm of the active ingredient and then applied.

The pesticidal composition of the present invention or a water dilution thereof may be applied directly to a pest or a plant such as a crop plant to be protected from the pest. Alternatively, the soil of a cultivated field may be treated with the pesticidal composition of the present invention or a water dilution thereof so as to control pests inhabiting the soil.

When the pesticidal composition of the present invention is in the form of resin formulation, it can be processed into the form of a sheet or a string, and then applied by winding it around a crop plant, disposing it in the vicinity of a crop plant, laying it on the soil surface at the plant feet, or the like.

When the pesticidal composition of the present invention is used for control of epidemic, the application amount is usually 0.001 to 10 mg/m ³ of the compound of the

present invention as the active ingredient for application to space, and 0.001 to 100 mg/m ² of the compound of the present invention as the active ingredient for application to a plane. The pesticidal composition in the form of an emulsifiable concentrate, a wettable powder or a flowable formulation is usually applied after dilution with water so as to contain usually 0.001 to 10,000 ppm of the active ingredient. The pesticidal composition in the form of an oil solution, an aerosol formulation, a smoking pesticide or a poison bait is usually applied as it is.

When the pesticidal composition of the present invention is used for controlling external parasites of livestock such as a cow, a horse, a pig, a sheep, a goat and a chicken, or small animals such as a dog, a cat, a rat and a mouse, it can be applied to said animals by a known method in the veterinary field. Specifically, when systemic control is intended, the pesticidal composition of the present invention is administered, for example, as a tablet, a mixture with feed, a suppository or an injection (e.g., intramuscularly, subcutaneously, intravenously, intraperitoneally, etc.). When non-systemic control is intended, a method of using the pesticidal composition of the present invention includes spraying, pour-on treatment or a spot-on treatment with the pesticidal composition in the form of an oil solution or an aqueous liquid, washing

an animal with the pesticidal composition in the form of a shampoo formulation, and attachment of a collar or a ear tag made of the pesticidal composition in the form of a resin formulation to an animal. When administered to an animal, the amount of the compound of the present invention is usually in the range of 0.1 to 1,000 mg per 1 kg body weight of the animal .

EXAMPLES

The present invention will be illustrated further in detail by production examples, reference production examples, formulation examples and test examples shown below, but the present invention is not limited thereto.

In the following production examples and reference production examples, for example, an analysis means using TLC (Thin Layer Chromatography) was used for reaction check or check of an eluate in a column chromatography operation.

For the reagent for TLC, Kiesel Gel 60F 254 (70 to 230 mesh) manufactured by Merck or a detection method by UV light were used. As the reagent for column chromatography, for example, silica gel 60 (spherical, particle size: 63 to 210 nm) manufactured by Kanto Chemical Co., Inc., or Florisil (100 to 200 mesh) manufactured by Wako Pure Chemical Industry Inc. was used. In medium pressure preparative HPCL, for example, Ultrapack (filler: silica

gel) manufactured by Yamazen K. K. were used. In NMR spectrum analysis, tetramethylsilane was used as an internal standard, and for example, JEOL AL-400 Bruker AVANCE 400 was used (measurement temperature was 25°C unless otherwise stated) . For measurement of the melting point, for example, trace amount melting point measurement meter manufactured by Yanagimoto Seisakusho K. K. were used.

In the present specification, abbreviations or terms show below have the following meanings. s: singlet, br: broad (wider), brs : broad singlet (wider singlet) , d: doublet, m: multiplet, dd: double doublet, t: triplet, J: coupling constant, Hz: herz; room temperature; about 15 to 25°C

Next, production examples of the compound of the present invention are shown below.

Production Example 1

(1) Production of N- [l-phenyl-3- (phenylthio) -2- propenylidene] aniline (Hereinafter, described as the present compound 1)

To a chloroform solution (5 mL) of N-(I- phenylpropinylidene) aniline (0.5 g) was added thiophenol (0.26 g) and triethylamine (catalytic amount) under ice cool, and the mixture was stirred for 2 hours under ice

cool, then, concentrated under reduced pressure condition. The resultant residue was subjected to silica gel column chromatography (hexane : ethyl acetate = 10:1) to obtain the present compound 1 (0.63 g) as a yellow oil.

¹ H-NMR (CDCl ₃ ) δ(ppm): 6.33 (IH, d, J = 15.9 Hz), 6.78 to 6.98 (3H, m) , 6.94 (IH, d, J = 15.9 Hz), 7.04 to 7.70 (12H, m)

Production Examples 2 to 206

The following compounds were produced according to the production method in Example 1.

(2) N- [l- (4-chlorophenyl) -3- ( 3 -fluorophenylthio) -2- propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 2" . )

¹ H-NMR(CDCl ₃ )O(PPm): 6.23 (0.8H, d, J=15.9Hz) , 6.47(0.2H,d, J=9.8Hz), 6.46—7.83 (14H,m)

(3) N- Cl- (4-chlorophenyl) -3- (4 -fluorophenylthio) -2- propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 3".)

¹ H-NMR(CDCl ₃ ) δ(ppm) : 6.04 (IH, d, J=IB .6Hz) , 6.74 ~7.64 (l4H,m)

(4) N- Cl- (4-chlorophenyl) -3- (2 -chlorophenylthio) -2- propenylidene) aniline (Hereinafter, this compound is referred to as "present compound 4".)

¹ H-NMR(CDCl ₃ )δ(ppm) : 6.17 (IH, d, J=IB .6Hz) ,6.78~7.65 (l4H,m)

(5) N- Cl- (4-chlorophenyl) -3- (3 -chlorophenylthio) -2-

propenylidene) aniline (Hereinafter, this compound is referred to as "present compound 5" . )

¹ H-NMR(CDCl ₃ )δ(ppm) : 6.22 (IH, d, J=15.6Hz) ,6.78— 7.68 (14H,m)

(6) N- [l- (4-chlorophenyl) -3- (4-chlorophenylthio) -2- propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 6".)

¹ H-NMR(CDCl ₃ ) δ (ppm) : 6.13 (lH,d, J=15.6Hz) , 6.74 —7.66 (14H,m)

(7) N- [l- (4-chlorophenyl) -3- (2-bromophenylthio) -2- propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 7" . )

¹ H-NMR(CDCl ₃ ) δ (ppm) : 6.19 (IH, d, J=15.9Hz) , 6.78 ~7.66 (14H,m)

(8) N- Cl- (4-chlorophenyl) -3- (3-bromophenylthio) -2- propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 8" . )

¹ H-NMR(CDCl ₃ )δ(ppm) : 6.22 (IH, d, J=15.9Hz) ,6.46 —7.68 (14H,m)

(9) N- Cl- (4-chlorophenyl) -3- (4-bromophenylthio) -2- propenylidene) aniline (Hereinafter, this compound is referred to as "present compound 9" .)

¹ H-NMR(CDCl ₃ ) δ(ppm) : 6.14 ( 0.8H, d, J=15.6Hz) , 6.22(0.2H,d, J=15.6Hz) ,6.45—7.66 (14H,m)

(10) N- Cl- (4-chlorophenyl) -3- (3- trifluoromethylphenylthio) -2-propenylidene) aniline (Hereinafter, this compound is referred to as "present compound 10" .) 1H-NMR(CDCl ₃ )δ (ppm) : 6.23 (IH, d, J=15.6Hz) , 6.30~7.85 (14H,m)

(11) N- [l- (4-chlorophenyl) -3- (2-methylphenylthio) -2- propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 11".) 1H-NMR(CDCl ₃ ) δ (ppm) : 2.32 (2.5H) ,2.33(0.5H ₇ S) ₇

5.93 (0.8H,d, J=15.4Hz) , 6.27 (0.2H, d, J=15.4Hz) , 6.55~ 7.61 (14H,m)

(12) N- [l- (4-chlorophenyl) -3- (4-methylphenylthio) -2- propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 12" .) 1H-NMR(CDCl ₃ ) δ (ppm) : 2.31(2.4H,s) ,2.32(0.6H,s) ,

6.10 (0.8H,d, J=15.6Hz) , 6.39 (0.2H, d, J=15.6Hz) ,6.52~ 7.84 (14H,m)

(13) N- [l- (4-chlorophenyl) -3- (2, 4-dimethylphenylthio) -2- propenylidene) aniline (Hereinafter, this compound is referred to as "present compound 13".)

¹ H-NMR(CDCl ₃ )δ(ppm) : 2.27 (4.5H, s) , 2.29 (1.5H, s) , 5.83 (0.8H,d, J=15.4Hz) , 6.18 (0.2H, d, J=15.4Hz) ,6.54 — 7.60 (13H,m)

(14) N- Cl- (4-chlorophenyl) -3- (3-methoxyphenylthio) -2- propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 14".)

¹ H-NMR(CDCl ₃ ) δ(ppm) : 3.72 (3H,s) ,6.23 (IH, d, J=15.6Hz) ,6.71— 7.81(14H,m)

(15) N- Cl- (4-chlorophenyl) -3- (4 -methoxyphenylthio) -2- propenylidene] aniline (Hereinafter, this compound is

referred to as "present compound 15" . ) 1H-NMR(CDCl ₃ )δ(ppm) : 3.79 (2.2H, s) , 3.80 (0.4H,s) , 3.82(0.4H,s), 5.99 (0.8H, d, J=15.6Hz) ,6.29 (0.2H, d, J=15.6Hz) , 6.35—7.60 (14H,m)

(16) N- [l- (4-chlorophenyl) -3- (2 , 4-dichlorophenylthio) -2- propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 16" .)

¹ H-NMR(CDCl ₃ )δ (ppm) : 6.10 (0.8H, d, J=15.6Hz) , 6.47 (0.2H,d, J=15.6Hz) , 6.57— 7.64 (13H,m)

(17) N- (l- (4-chlorophenyl) -3- (4-nitrophenylthio) -2- propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 17" .) 1H-NMR(CDCl ₃ )δ(ppm) : 6.42 —6.60 (lH,m) , 6.65~8.24 (14H,m)

(18) N- (l-phenyl-3- (2-fluorophenylthio) -2-propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 18".)

¹ H-NMR(CDCl ₃ )δ(ppm) : 6.13 (0.8H, d, J=15.6Hz) ,6.20 — 6.40 (0.2H,m) , 6.42 —7.92 (15H,m)

(19) N- (l-phenyl-3- (3-fluorophenylthio) -2-propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 19" . )

¹ H-NMR(CDCl ₃ )δ(ppm) : 6.28 (0.9H, d, J=15.6Hz) , 6.53 ( 0. IH, d, J=ICOHz) , 6.57~7.71 (15H,m)

(20) N- (l-phenyl-3- (4 -fluorophenylthio) -2-propenylidene] aniline (Hereinafter, this compound is referred to as

"present compound 20".)

¹ H-NMR ( CDCl ₃ ) δ (ppm) : 6 . 07 ( 0 . 7H , d , J=15 . 6Hz ) , 6 . 20 —

6 . 48 ( 0 . 3H , m) , 6 . 57 ~ 7 . 97 ( 15H , m)

(21) N- (l-phenyl-3- (2-chlorophenylthio) -2-propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 21".)

¹ H-NMR(CDCl ₃ )δ (ppm) : 6.21 (0.8H, d, J=15.6Hz) , 6.54 (0.2H,d, J=15.6Hz), 6.52—7.70 (15H,m)

(22) N- [l-phenyl-3- (3-chlorophenylthio) -2-propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 22" .)

¹ H-NMR(CDCl ₃ ) δ (ppm) :6.26 (0.7H, d, J=15.6Hz) , 6.56(0.3H,d, J=15.6Hz), 6.52—7.88 (15H,m)

(23) N- [l-phenyl-3- (4-chlorophenylthio) -2-propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 23" .)

¹ H-NMR(CDCl ₃ )δ (ppm) : 6.17 (0.8H, d, J=15.6Hz) , 6.43(0.2H,d, J=15.6Hz), 6.50—7.97(15H,m)

(24) N- [l-phenyl-3- (2-bromophenylthio) -2-propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 24" .)

¹ H-NMR(CDCl ₃ ) δ (ppm) :6.24 (0.8H, d, J=15.6Hz) , 6.57 (0.2H,d, J=15.6Hz) ,6.60—7.71 (15H,m)

(25) N- [l-phenyl-3- (3-bromophenylthio) -2-propenylidene] aniline (Hereinafter, this compound is referred to as

"present compound 25" . )

¹ H-NMR(CDCl ₃ )δ (ppm) :6.26 (0.7H, d, J=15.6Hz) , 6.53 (0.3H,d,

J=9.8Hz) , 6.59 — 7.69 (15H,m)

(26) N- (l-phenyl-3- (4-bromophenylthio) -2-propenylidene) aniline (Hereinafter, this compound is referred to as "present compound 26" .)

¹ H-NMR(CDCl ₃ ) δ (ppm) :6.18 (0.8H, d, J=15.6Hz) , 6.50 (0.2H,d, J=15.6Hz), 6.50—7.67(15H,m)

(27) N- [l-phenyl-3- (3-trifluoromethylphenylthio) -2- propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 27" .)

¹ H-NMR(CDCl ₃ ) δ (ppm) :6.28 (0.8H, d, J=15.9Hz) , 6.36(0.2H,d, J=IO.7Hz), 6.58—7.67 (15H,m)

(28) N- (l-phenyl-3- (2-methylphenylthio) -2-propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 28" .)

¹ H-NMR(CDCl ₃ ) δ (ppm) : 2.32 (2.4H, s) , 2.45 (0.6H, s) , 5.97 (0.7H,d, J=15.4Hz) ,6.30 (0.3H,d, J=15.4Hz) , 6.57~7.66 (15H,m)

(29) N- [l-phenyl-3- (3-methylphenylthio) -2-propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 29".)

¹ H-NMR(CDCl ₃ )δ(ppm) : 2.28 (2.4H, s) , 2.35 (0.6H, s) , 5.97(0.8H,d, J=15.6Hz), 6.30 (0.2H,d,J=15.6Hz) ,6.58—7.68 (15H,m)

(30) N- [l-phenyl-3- (4-methylphenylthio) -2-propenylidene) aniline (Hereinafter, this compound is referred to as

"present compound 30".)

¹ H-NMR(CDCl ₃ )δ(ppm) : 2.30 (2.3H, s) , 2.35 (0.7H, s) , 6.14 (0.8H,d,

J=15.6Hz) ,6.42 (0.2H,d, J=15.6Hz) ,6.56 — 7.66 (15H,m)

(31) N- [l-phenyl-3- (2 , 4-dimethylphenylthio) -2- propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 31".)

¹ H-NMR(CDCl ₃ )O(PPm) : 2.26 (2.4H, s) , 2.28 (2.4H, s) , 2.33 (0.6H, s) ,2.42(0.6H,s),5.86(0.8H, d, J=15.4Hz) ,6.21 (0.2H, d, J=15.4Hz) , 6 .56—7.65 (14H,m)

(32) N- [l-phenyl-3- (3-methoxyphenylthio) -2-propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 32" .)

¹ H-NMR(CDCl ₃ )δ(ppm) : 3.77 (2.3H, s) , 3.80 (0.7H ₇ s) , 6.27 (0.7H,d, J=15.6Hz) ,6.56 (0.3H, d, J=15.6Hz) ,6.59—7.68 (15H,m)

(33) N- [l-phenyl-3- (4-methoxyphenylthio) -2-propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 33".)

¹ H-NMR(CDCl ₃ ) δ (ppm) :3.78(2.3H,s) ,3.82(0.7H,s) , β.02(0.7H,d, J=15.6Hz) ,6.31(0.3H,d, J=15.6Hz) ,6.41—7.65 (15H,m)

(34) N- [l-phenyl-3- (2, 4-dichlorophenylthio) -2- propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 34" .)

¹ H-NMR (CDCl ₃ )δ (ppm) : 6.14 (0.9H, d, J=15.6Hz) , 6.51(0. IH, d, J=15.6Hz), 6.59—7.69 (14H,m)

(35) N- [l-phenyl-3- (3, 5-dichlorophenylthio) -2-

propenylidene) aniline (Hereinafter, this compound is referred to as "present compound 35".) 1H-NMR(CDCl ₃ )δ(ppm) : 6.31 (0.8H, d, J=15.9Hz) , 6.38— 6.57 (1.2H,m) , 6.58~7.67 (13H,m)

(36) N- [l-phenyl-3- (4-nitrophenγlthio) -2-propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 36".)

¹ H-NMR(CDCl ₃ )δ (ppm) :6.40~8.27 (16H,m)

(37) N- Cl- (3-methylphenyl) -3- (2-fluorophenylthio) -2- propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 37".)

¹ H-NMR(CDCl ₃ )δ(ppm) :2.30(0.5H,s),2.37(0.5H,s),2.40(2H,s), 6.13 (0.7H,d, J=15.6Hz) ,6.42 (0.3H, d, J=15.6Hz) ,6.48~ 7.50 (14H,m)

(38) N- Cl- (3-methylphenyl) -3- (3 -fluorophenylthio) -2- propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 38".) 1H-NMR(CDCl ₃ ) δ (ppm) :2.39(0.6H,s),2.41(2.4H,s),

6.27 (0.7H, d, J=15.6Hz) ,6.50~6.58(0.3H,m),6.60~7.74 (14H,m)

(39) N- Cl- (3-methylphenyl) -3- (4 -f luorophenylthio) -2- propenylidene) aniline (Hereinafter, this compound is referred to as "present compound 39".)

¹ H-NMR(CDCl ₃ )δ(ppm) : 2.37 (0.5H, s) , 2.40 (2.3H, s) , 2.42 (0.2H, s) , 6.07 (0.8H,d,J=15.6Hz) ,6.37 (0.2H, d, J=15.6Hz) ,6.45~ 7.75(l4H,m)

(40) N- [l- (3-methylphenyl) -3- (2-chlorophenylthio) -2- propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 40".)

¹ H-NMR(CDCl ₃ )δ(ppm) : 2.35(0.5H,s),2.41(2.5H,s), 6.22(0.8H,d, J=15.6Hz) ,6.53 (0.2H, d, J=15.6Hz) ,6.84—7.52 (14H,m)

(41) N- [l- (3-methylphenyl) -3- (3-chlorophenylthio) -2- propenylidene) aniline (Hereinafter, this compound is referred to as "present compound 41" .)

¹ H-NMR(CDCl ₃ )δ(ppm) : 2.35 (0.2H, s) , 2.41 (0.4H, s) , 2.42 (2.4H, s) ,

6.27 (0.8H,d,J=15.6Hz) , 6.31 ( 0.2H, d, J=IO .5Hz) , 6.50~ 7.74 (14H,m)

(42) N- [l- (3-methylphenyl) -3- (4-chlorophenylthio) -2- propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 42".)

¹ H-NMR(CDCl ₃ )δ(ppm) : 2.38 (0.3H, s) , 2.41 (2.3H, s) , 2.42 (0.4H, s) , 6.16 (0.8H,d, J=15.4Hz) , 6.47 (0.2H, d, J=15.6Hz) ,6.48— 7.74 (14H,m)

(43 ) N- Cl- (3-methylphenyl) -3- (2-bromophenylthio) -2- propenylidene) aniline (Hereinafter, this compound is referred to as "present compound 43".)

¹ H-NMR(CDCl ₃ )δ(ppm) :2.41(3H,s) , 6.24 (lH,d, J=15.6Hz) ,6.52— 7.74 (14H,m)

(44) N- Cl- (3-methylphenyl) 3- (3-bromophenylthio) -2- propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 44" . )

¹ H-NMR(CDCl ₃ )δ (ppm) :2.42 (3H,s) , 6.27 (IH, d, J=15.9Hz) ,6.53— 7.74 (14H,m)

(45) N- Cl- (3-methylphenyl) -3- (4-bromophenylthio) -2- propenylidene) aniline (Hereinafter, this compound is referred to as "present compound 45" .)

¹ H-NMR(CDCl ₃ ) δ (ppm) :2.39(0.6H,s),2.41(2.4H,s), 6.18 (0.8H,d, J=15.6Hz) ,6.48 (0.2H, d, J=15.6Hz) ,6.71—7.74 (14H,m)

(46) N- Cl- (3-methylphenyl) -3- (3- trifluoromethylphenylthio) -2-propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 46" .)

¹ H-NMR(CDCl ₃ ) δ (ppm) :2.41 (3H,s) ,6.28 (IH, d, J=15.6Hz) ,6.54— 7.79 (14H,m)

(47) N- Cl- (3-methylphenyl) -3- (2-methylphenylthio) -2- propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 47" . )

¹ H-NMR(CDCl ₃ )δ(ppm) :2.31 (0.4H, s) , 2.33 (2.6H, s) , 2.6 (2.6H, s) , 2.42(0.4H,s) ,5.98 (0.8H, d, J=15.4Hz) , 6.28(0.2H,d, J=15.4Hz), 6.57—7.75 (14H,m)

(48) N- Cl- (3-methylphenyl) -3- (3-methylphenylthio) -2- propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 48".)

¹ H-NMR(CDCl ₃ )δ(ppm) : 2.22—2.43 (6H,m) , 6.22 (0.8H, d, J=15.6Hz) , 6.48 (0.2H,d, J=15.6Hz) ,6.58—7.74 (14H,m)

(49) N- Cl- (3-methylphenyl) -3- (4-methylphenylthio) -2-

propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 49".)

¹ H-NMR(CDCl ₃ ) δ (ppm) :2.30(2.5H,s) ,2.32(0.5H,s) ,2.35(0.5H,s) , 2.40(2.5H,s) ,6.13 (0.8H, d, J=15.6Hz) , 6.40 (0.2H, d, J=15.6Hz) ,6. 43 —7.74 (14H,m)

(50) N- [l- (3-methylphenyl) -3- (2 , 4-dimethylphenylthio) -2- propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 50" .)

¹ H-NMR(CDCl ₃ )δ(ppm) : 2.22 ~2.33 (6H, m) , 2.38 —2.43 (3H, s) , 5.86(0.8H,d, J=15.4Hz) , 6.19 (0.2H, d, J=15.4Hz) , 6.56 —7.47 (14H,m)

(51) N- [l- (3-methylphenyl) -3- (3 -methoxyphenylthio) -2- propenylidene) aniline (Hereinafter, this compound is referred to as "present compound 51" . )

¹ H-NMR(CDCl ₃ ) δ (ppm) :2.36(1.5H,s) ,2.41(1.5H,s) ,3.70(1.5H,s) , 3.77 (1.5H,s) ,6.27 (0.5H, d, J=15.9Hz) ,6.39 —7.73 (14.5H,m)

(52) N- Cl- (3-methylphenyl) -3- (4 -methoxyphenylthio) -2- propenylidene) aniline (Hereinafter, this compound is referred to as "present compound 52".)

¹ H-NMR(CDCl ₃ ) δ (ppm) :2.35(1.8H,s),2.40(1.2H,s),3.79 (3H,s) , 6.27(0.2H,d, J=15.9Hz) ,6.39—7.73 (14.8H,m)

(53) N- Cl- (3-methylphenyl) -3- (2 , 4-dichlorophenylthio) -2- propenylidene) aniline (Hereinafter, this compound is referred to as "present compound 53".)

¹ H-NMR(CDCl ₃ )δ(ppm) :2.41(3H,s) , 6.15 (0.6H, d, J=15.6Hz) ,

6 . 80 ( 0 . 4H , d , J=15 . 6Hz ) , 6 . 82 — 7 . 51 ( 13H , m)

(54) N- [l- (3-methylphenyl) -3- (3 , 5-dichlorophenylthio) -2- propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 54".)

¹ H-NMR(CDCl ₃ ) δ (ppm) :2.27(0.4H,s),2.43(2.6H,s), 6.33 (0.85H, d, J=15.6Hz) ,6.56 (0.15H, d, J=IO .5Hz) ,6.35—7.52 (13H,m)

(55) N- Cl- (3-methylphenyl) -3- (4-nitrophenylthio) -2- propenylidene) aniline (Hereinafter, this compound is referred to as "present compound 55" .)

¹ H-NMR(CDCl ₃ ) δ (ppm) : 2.42 (1.4H, s) , 2.43 (1.6H,s) , 6.43 (0.4H,d, J=15.6Hz) ,6.48—8.20 (14.6H,m)

(56) N- Cl- (4-methylphenyl) -3- (2-fluorophenylthio) -2- propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 56" .)

¹ H-NMR(CDCl ₃ ) δ (ppm) : 2.40 (3H, s) , 6.13 (IH, d, J=15.6Hz) , 6.82~ 7.32 (12H,m) ,7.57 (2H, d, J=8. OHz)

(57) N- Cl- (4-methylphenyl) -3- (3-fluorophenylthio) -2- propenylidene) aniline (Hereinafter, this compound is referred to as "present compound 57" .)

¹ H-NMR(CDCl ₃ )δ (ppm) :2.40 (3H,s) , 6.27 (IH, d, J=15.9Hz) ,6.83~ 7.32(12H,m) ,7.58 (2H, d, J=8. OHz)

(58) N- Cl- (4-methylphenyl) -3- (4 -fluorophenylthio) -2 - propenylidene) aniline (Hereinafter, this compound is referred to as "present compound 58".)

¹ H-NMR(CDCl ₃ ) δ(ppm) :2.40(3H,s),6.07 (IH, d, J=15.6Hz) ,6.82~

7 . 32 ( HH , m) , 6 . 86 ( IH , d , J=15 . 6Hz ) , 7 . 56 ( 2H , d , J= 8 . OHz )

(59) N- [l- (4-methylphenyl) -3- (2-chlorophenylthio) -2- propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 59" .)

¹ H-NMR(CDCl ₃ ) δ (ppm) :2.40(3H,s) ,6.22 (IH, d, J=15.6Hz) , 6.48~ 6.61 (IH, m) ,6.83 —7.32 (llH,m) , 7.59 (2H, d, J=8. OHz)

(60) N- [l- (4-methylphenyl) -3- (3-chlorophenylthio) -2- propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 60" .)

¹ H-NMR(CDCl ₃ ) δ (ppm) :2.40(3H,s) ,6.25 (IH, d, J=15.6Hz) ,6.83~ 7.34 (llH,m) , 6.88 (IH, d, J=15.6Hz) ,7.58 (2H, d, J=8. OHz)

(61) N- [l- (4-methylphenyl) -3- (4-chlorophenylthio) -2- propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 61" . )

¹ H-NMR(CDCl ₃ ) δ (ppm) :2.40(3H,s),6.17 (IH, d, J=15.6Hz) ,6.80~ 7.30 (llH,m) , 6.87 (IH, d, J=15.6Hz) ,7.56 (2H, d, J=8. OHz)

(62) N- [l- (4-methylphenyl) -3- (2-bromophenylthio) -2- propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 62" .)

¹ H-NMR(CDCl ₃ ) δ (ppm) :2.40 (3H,s) ,6.24 (IH, d, J=15.6Hz) ,6.84~ 7.61(13H,m)

(63) N- [l- (4-methylphenyl) 3- (3-bromophenylthio) -2- propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 63".)

¹ H-NMR(CDCl ₃ ) δ(ppm) : 2.40 (3H, s) , 6.25 (IH, d, J=15.6Hz) ,6.83~

7 . 46 ( llH , m) , 6 . 88 ( IH , d , J=15 . 6Hz ) , 7 . 58 ( 2H , d , J= 8 . OHz )

(64) N- [l- (4-methylphenyl) -3- (4-bromophenylthio) -2- propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 64" .)

¹ H-NMR(CDCl ₃ )δ(ppm) : 2.40 (3H, s) , 6.18 (IH, d, J=15.6Hz) , 6.79~ 7.50 (llH,m) ,6.86 (IH, d, J=15.6Hz) ,7.56 (2H, d, J=8. OHz)

(65) N- (l- (4-methylphenyl) -3- (3- trifluoromethylphenylthio) -2-propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 65" .)

¹ H-NMR(CDCl ₃ ) δ (ppm) :2.40(3H,s) ,6.27 (IH, d, J=15.6Hz) ,6.77~ 7.80(13H,m), 6.89 (IH, d, J=15.6Hz)

(66) N- [l- (4-methylphenyl) -3- (2-methylphenylthio) -2- propenylidenej aniline (Hereinafter, this compound is referred to as "present compound 66" .)

¹ H-NMR(CDCl ₃ ) δ (ppm) :2.27(0.9H,s),2.32(2.1H,s),2.39(2.1H,s), 2.45(0.9H,s),5.97 (0.7H, d, J=15.4Hz) ,6.29 ( 0.3H, d, J=15. IHz) ,6. 77—7.45(12H,m) , 7.55 (2H, d, J=8. OHz)

(67) N- [l- (4-methylphenyl) -3- (3-methylphenylthio) -2- propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 67".) 1H-NMR(CDCl ₃ )δ(ppm) : 2.29 (3H, s) , 2.40 (3H, s) , 6.21 (IH, d,

J=15.6Hz), 6.83 —7.32 (llH,m) , 6.94 (IH, d, J=15.6Hz) , 7.57 (2H,d, J=8.0Hz)

(68) N- [l- (4-methylphenyl) -3- (4-methylphenylthio) -2-

propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 68" .)

¹ H-NMR(CDCl ₃ ) δ (ppm) : 2.30 (3H,s) , 2.39(3H,s), 6.12(lH,d, J=15.6Hz) ,6.77—7.37 (llH,m) , 6.92 (IH, d, J=15.6Hz) , 7.55(2H, d, J=8.0Hz)

(69) N- [l- (4-methylphenyl) -3- (2 , 4-dimethylphenylthio) -2- propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 69" .)

¹ H-NMR(CDCl ₃ ) δ(ppm) :2.26(3H,s),2.27(3H,s),2.39(3H,s), 5.85(lH,d, J=15.6Hz) ,6.74—7.36 (10H,m) ,6.84 (IH, d, J=15.6Hz) , 7.54 (2H,d, J=8.0Hz)

(70) N- [l- (4-methylphenyl) -3- (3 -methoxyphenylthio) -2- propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 70" .) 1H-NMR(CDCl ₃ ) δ (ppm) :2.40(3H,s),3.77(3H,s),6.26(lH,d,

J=15.6Hz) , 6.76—7.33 (llH,m) ,6.96 (IH, d, J=15.6Hz) , 7.57 (2H,d, J=8.0Hz)

(71) N- [l- (4-methylphenyl) -3- (4-methoxyphenylthio) -2- propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 71" . ) 1H-NMR(CDCl ₃ ) δ (ppm) :2.26(0.42H,s),2.39(2.58H,s),

3.78 (1.70H, s) , 3.80 (0.85H,s) , 3.82 (0.45H, s) , 6.00 (0.57H,d, J=15.6Hz) , 6.30 (0.28H, d, J=15.4Hz) , 6.58 (0.15H,d, J=7.8Hz) , 6.77—7.55 (14H,m)

(72) N- Cl- (4-methylphenyl) -3- (2, 4-dichlorophenylthio) -2-

propenylidene) aniline (Hereinafter, this compound is referred to as "present compound 72" .)

¹ H-NMR(CDCl ₃ )δ (ppm) : 2.40 (3H, s) , 6.15 (IH, d, J=15.6Hz) ,6.77— 7.39(llH,m),7.58 (2H, d, J=8. OHz)

(73) N- [l- (4-methylphenyl) -3- (3 , 5-dichlorophenγlthio) -2- propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 73".)

¹ H-NMR(CDCl ₃ ) δ (ppm) :2.41(3H,s) , 6.31 (IH, d, J=15.9Hz) , 6.77~ 7.35(llH,m), 7.59 (2H, d, J=8. OHz)

(74) N- [l- (4-methylphenyl) -3- (4-nitrophenylthio) -2- propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 74" .)

¹ H-NMR(CDCl ₃ ) δ(ppm) : 2.41—2.44 (3H,m) , 6.48—6.55 (lH,m) , 6.89— 8.18 (14H,m)

(75) N- [l- (4-trifluoromethylphenyl) -3- (2- fluorophenylthio) -2-propenylidene) aniline (Hereinafter, this compound is referred to as "present compound 75" . ) ¹ H-NMR(CDCl ₃ ) δ (ppm) : 6.13 (IH, d, J=15.6Hz) ,6.76—7.79 (14H,m)

(76) N- [l- (4-trifluoromethylphenyl) -3- (3- fluorophenylthio) -2-propenylidene) aniline (Hereinafter, this compound is referred to as "present compound 76" . ) ¹ H-NMR(CDCl ₃ )δ(ppm) : 6.25 (IH, d, J=15.6Hz) ,6.83—7.80 (14H,m)

(77) N- Cl- (4-trifluoromethylphenyl) -3- (4- fluorophenylthio) -2-propenylidene) aniline (Hereinafter, this compound is referred to as "present compound 77".)

¹ H-NMR(CDCl ₃ ) δ(ppm) :6.06 (IH, d, J=15.6Hz) , 6.76~7.51 (1OH, m) , 7.73 (4H,dd, J ₁ =26. IHz, J ₂ =8. OHz)

(78) N- [l- (4-trifluoromethylphenyl) -3- (2- chlorophenylthio) -2-propenylidene) aniline (Hereinafter, this compound is referred to as "present compound 78" . ) ¹ H-NMR(CDCl ₃ ) δ (ppm) :6.18 (IH, d, J=15.6Hz) , 6.80~7.52 (1OH, m) , 7.75 (4H,dd, J ₁ =36.2Hz, J ₂ =8.2Hz)

(79) N- Cl- (4-trifluoromethylphenyl) -3- (3- chlorophenylthio) -2-propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 79".)

¹ H-NMR(CDCl ₃ )δ(ppm) :6.24 (IH, d, J=15.9Hz) ,6.82~7.53 (10H,m) , 7.75 (4H,dd, J ₁ =29. IHz, J ₂ =8.2Hz)

(80) N- Cl- (4-trifluoromethylphenyl) -3- (4- chlorophenylthio) -2-propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 80".) ¹ H-NMR(CDCl ₃ )δ(ppm) : 6.15 ( IH, d, J=15.9Hz) ,6.79~7.52 (10H,m) , 7.74 (4H,dd, J ₁ =27. IHz, J ₂ =8.3Hz)

(81) N- Cl- (4-trifluoromethylphenyl) -3- (2-bromophenylthio) - 2-propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 81" .)

¹ H-NMR(CDCl ₃ )δ(ppm) :6.20 ( IH, d, J=15.6Hz) ,6.80~7.82 (14H,m)

(82) N- Cl- (4-trifluoromethylphenyl) 3- (3 -bromophenylthio) - 2-propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 82" .)

¹ H-NMR(CDCl ₃ )δ(ppm) :6.24 ( IH, d, J=15.6Hz) ,6.82 —7.52 (10H,m) ,

7 . 75 ( 4H , dd , Ji =28 . 4Hz , J ₂ =8 . 2Hz )

(83) N- Cl- (4-trifluoromethylphenyl) -3- (4-bromophenylthio) - 2-propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 83".)

¹ H-NMR(CDCl ₃ ) δ (ppm) :6.16 (IH, d, J=15.6Hz) , 6.80~7.53 (10H,m) , 7.74 (4H,dd, Ji =26.8Hz, J ₂ =8. OHz)

(84) N- Cl- (4-trifluoromethylphenyl) -3- (3- trifluoromethylphenylthio) -2-propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 84.)

¹ H-NMR(CDCl ₃ ) δ (ppm) :6.25 (IH, d, J=15.6Hz) , 6.82~7.58 (1OH, m) , 7.75 (4H,dd, J _x =30.2Hz, J ₂ =8. OHz)

(85) N- Cl- (4-trifluoromethylphenyl) -3- (2- methylphenylthio) -2-propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 85".) ¹ H-NMR(CDCl ₃ )δ (ppm) :2.33(3H,s),5.9β (IH, d, J=15.6Hz) , 6.77~ 7.52 (9H,m) ,6.83 (IH, d, J=15.6Hz) ,7.73 (4H, dd, J ₁ =27. OHz, J ₂ =8.2H z)

(86) N- Cl- (4-trifluoromethylphenyl) -3- (3- methylphenylthio) -2-propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 86" .)

¹ H-NMR(CDCl ₃ )δ(ppm) :2.29(3H,s) , 6.21 (IH, d, J=15.6Hz) ,6.72— 7.50 (9H,m) ,6.90 (IH, d, J=15.6Hz) ,7.74 (4H, dd, Ji =31.8Hz, J ₂ =8.2H z)

(87) N- Cl- (4-trifluoromethylphenyl) -3- (4-

methylphenylthio) -2-propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 87" . )

¹ H-NMR(CDCl ₃ )δ(ppm) : 2.31 (3H, s) , 6.13 (IH, d, J=15.6Hz) , 6.78~ 7.50 (9H,m) ,6.88 (IH, d, J=15.6Hz) ,7.72 (4H, dd, Ji =28.9Hz, J ₂ =8.4H z)

(88) N- [l- (4-trifluoromethylphenyl) -3- (2,4- dimethylphenylthio) -2-propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 88" . ) ¹ H-NMR(CDCl ₃ ) δ (ppm) :2.27(3H,s) ,2.28 (3H,s) , 5.85 ( IH, d, J=15.6Hz), 6.75~7.50(8H,m) , 6.81 (IH, d, J=15.6Hz) ,

7.72 (4H,dd, J ₁ =24.4Hz, J ₂ =8.3Hz)

(89) N- [l- (4-trifluoromethylphenyl) -3- (3- methoxyphenylthio) -2-propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 89" . ) ¹ H-NMR(CDCl ₃ )δ(ppm) : 3.77 (3H, s) , 6.26 (IH, d, J=15.6Hz) ,6.75~ 7.51 ( 10H, m) , 7.74 (4H, dd, Ji =31. OHz, J ₂ =8. OHz)

(90) N- [l- (4-trifluoromethylphenyl) -3- (4- methoxyphenylthio) -2-propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 90" . ) ¹ H-NMR(CDCl ₃ )δ(ppm) : 3.79 (3H, s) , 6.02 (IH, d, J=15.6Hz) ,6.72~ 7.51 (1OH, m) ,7.72 (4H, dd, Ji =26.6Hz, J ₂ =8. OHz)

(91) N- [l- (4-trifluoromethylphenyl) -3- (2,4- dichlorophenylthio) -2-propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 91" .) ¹ H-NMR(CDCl ₃ )δ(ppm) :6.10 (IH, d, J=15.6Hz) ,6.76 (IH, d,

J= 15 . 6Hz ) , 6 . 82 ( 2H , dd , Ji = 8 . 3Hz , J ₂ = 1 . 2Hz ) , 7 . 07 — 7 . 52 ( 6H , m) , 7 . 75 ( 4H , dd , Ji =31 . 1Hz , J ₂ =8 . 2Hz )

(92) N- [l- (4-trifluoromethylphenyl) -3- (3,5- dichlorophenylthio) -2-propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 92".) ¹ H-NMR(CDCl ₃ )δ(ppm) :6.28 (IH, d, J=15.6Hz) ,6.80 (IH, d, J=15.6Hz), 6.83~6.86(2H,m) ,7.13 — 7.54 (6H,m) , 7.76(4H,dd, Ji =27.2Hz, J ₂ =8.2Hz)

(93) N- Cl- (4-trifluoromethylphenyl) -3- (4-nitrophenylthio) - 2-propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 93".)

¹ H-NMR(CDCl ₃ ) δ (ppm) :6.47 (IH, d, J=15.9Hz) , 6.85~8.21 (14H, m)

(94) N- [l- (3-chlorophenyl) -3- (2 -fluorophenylthio) -2- propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 94" .)

¹ H-NMR(CDCl ₃ ) δ(ppm) :6.09 (IH, d, J=15.6Hz) ,6.81— 7.67 (14H,m)

(95) N- Cl- (3-chlorophenyl) -3- (3-fluorophenylthio) -2- propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 95" .)

¹ H-NMR(CDCl ₃ )δ(ppm) :6.23 (IH, d, J=15.9Hz) ,6.80 —7.45 (llH,m) , 6.89 (lH,d, J=15.9Hz) , 7.53 ~7.56 (lH,m) , 7.67~7.69 (lH,m)

(96) N- Cl- (3-chlorophenyl) -3- (4-fluorophenylthio) -2- propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 96" .)

¹ H-NMR(CDCl ₃ )δ(ppm) :6.03 (IH, d, J=15.6Hz) ,6.76 —7.53 (12H,m) ,

6 . 85 ( IH , d , J= 15 . 6Hz ) , 7 . 65 — 7 . 66 ( lH , m)

(97) N- [l- (3-chlorophenyl) -3- (2-chlorophenylthio) -2- propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 97" .)

¹ H-NMR(CDCl ₃ ) δ (ppm) : 6.16 (IH, d, J=15.6Hz) , 6.82 ~7.69 (14H,m)

(98) N- Cl- (3-chlorophenyl) -3- (3-chlorophenylthio) -2- propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 98" . )

¹ H-NMR(CDCl ₃ )δ(ppm) :6.22 (IH, d, J=15.9Hz) , 6.82 — 6.84 (2H,m) , 6.88 (IH, d, J=15.9Hz) , 7.08 —7.45 (9H,m) ,7.53 —7.55 (IH, m) , 7.68 — 7.69 (IH, m)

(99) N- Cl- (3-chlorophenyl) -3- (4-chlorophenylthio) -2- propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 99" .)

¹ H-NMR(CDCl ₃ ) δ (ppm) : 6.12 (IH, d, J=15.9Hz) ,6.79 — 6.81 (2H,m) , 6.86 (IH, d, J=15.9Hz) , 7.08~ 7.44 ( 9H,m) , 7.52 —7.54 (IH, m) , 7.66 — 7.67(lH,m)

(100) N- Cl- (3-chlorophenyl) -3- (2 -bromophenylthio) -2- propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 100" . )

¹ H-NMR(CDCl ₃ ) δ(ppm) .6.18 (IH, d, J=15.6Hz) , 6.83 ~6.87 (3H,m) , 7.07—7.45 (9H,m) ,7.55 — 7.58 (IH, m) ,7.70 — 7.72 (IH, m)

(101) N- Cl- (3-chlorophenyl) 3- (3 -bromophenylthio) -2- propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 101" . )

¹ H-NMR(CDCl ₃ )δ(ppm) : 6.22 (IH, d, J=15.9Hz) ,6.82 — 7.68 (14H,m)

(102) N- [l- (3-chlorophenyl) -3- (4-bromophenylthio) -2- propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 102" . )

¹ H-NMR(CDCl ₃ ) δ (ppm) : 6.14 (IH, d, J=15.6Hz) ,6.79~6.81(2H,m) , 6.86 (IH, d, J=15.6Hz) , 7.08~7.44 (9H,m) , 7.51~7.54 (lH,m) , 7.66 ~ 7.67(lH,m)

(103) N- [l- (3-chlorophenyl) -3- (3- trifluoromethylphenylthio) -2-propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 103" .)

¹ H-NMR(CDCl ₃ )δ (ppm) :6.22 (lH,d, J=15.9Hz) , 6.80 ~6.83 (2H,m) , 6.89 (IH, d, J=15.9Hz) ,7.07~7.69(llH,m)

(104) N- Cl- (3-chlorophenyl) -3- (2 -methylphenylthio) -2- propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 104" . )

¹ H-NMR(CDCl ₃ ) δ (ppm) :2.33(3H,s) ,5.93 (IH, d, J=15.6Hz) ,6.74~ 6.78 (2H,m) ,6.86 (IH, d, J=15.6Hz) ,7.03~7.53(10H,m),7.66~ 7.66 (IH, m)

(105) N- Cl- (3-chlorophenyl) -3- (3 -methylphenylthio) -2- propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 105" . )

¹ H-NMR(CDCl ₃ ) δ (ppm) :2.29(3H,s) , 6.19 (IH, d, J-=15.6Hz) ,6.82~ 6.84 (2H,m) ,6.93 (IH, d, J=15.6Hz) ,7.08~7.55(10H,m) , 7.68(lH,brs)

(106) N- [l- (3-chlorophenyl) -3- (4-methylphenylthio) -2- propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 106" . )

¹ H-NMR(CDCl ₃ ) δ (ppm) :2.32(3H,s) ,6.09 (IH, d, J=15.6Hz) , 6.79~ 6.82 (2H,m) ,6.90 (IH, d, J=15.6Hz) , 7.07—7.42 (9H,m) , 7.51~ 7.53 (IH, m) ,7.65—7.67 (IH, m)

(107) N- [l- (3-chlorophenyl) -3- (2 , 4-dimethylphenylthio) -2- propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 107" . )

¹ H-NMR(CDCl ₃ )δ(ppm) : 2.27 (3H, s) , 2.28 (3H, s) , 5.82 (IH, d, J=15.6Hz), 6.73 —6.76 (2H,m) , 6.84 (IH, d, J=15.6Hz) , 6.90—

7.42 (8H,m) ,7.50—7.52 (IH, m) , 7.63 —7.64 (lH,m)

(108) N- [l- (3-chlorophenyl) -3- (3 -methoxyphenylthio) -2- propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 108".)

¹ H-NMR(CDCl ₃ ) δ (ppm) :3.77(3H,s),6.23 (IH, d, J=15.6Hz) ,6.82 —

7.43 (llH,m) ,6.94 (IH, d, J=15.6Hz) , 7.52—7.55 (IH, m) , 7.67— 7.68 (IH, m)

(109) N- [l- (3-chlorophenyl) -3- (4 -methoxyphenylthio) -2- propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 109" . )

¹ H-NMR(CDCl ₃ )δ (ppm) : 3.79 (3H, s) , 5.98 (IH, d, J=15.6Hz) ,6.78— 7.53(13H,m) ,7.65(lH,br)

(110) N- [l- (3-chlorophenyl) -3- (2, 4-dichlorophenylthio) -2- propenylidene] aniline (Hereinafter, this compound is

referred to as "present compound 110" . ) 1H-NMR(CDCl ₃ ) δ (ppm) :6.09 (IH, d, J=15.6Hz) ,6.11— 6.82(3H,m),7.11~7.45(8H,m),7.54~7.56(lH,m),7.68~ 7.69 (IH, m)

(111) N- [l- (3-chlorophenyl) -3- (3 , 5-dichlorophenylthio) -2- propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 111" . )

¹ H-NMR(CDCl ₃ ) δ (ppm) :6.27 (IH, d, J=15.9Hz) ,6.83 (IH, d, J=15.9Hz), 6.80—7.70 (12H,m)

(112) N- [l- (3-chlorophenyl) -3- (4-nitrophenylthio) -2- propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 112" . ) 1H-NMR(CDCl ₃ ) δ (ppm) :6.45 (IH, d, J=15.9Hz) , 6.91 (IH, d, J=15.9Hz), 6.84—8.20 (13H,m)

(113) N- [l- (4-methoxyphenyl) -3- (2-fluorophenylthio) -2- propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 113" . )

¹ H-NMR(CDCl ₃ ) δ(ppm) :3.85(3H,s),6.11 (IH, d, J=15.6Hz) ,6.65~ 7.35 (12H,m) ,7.66 (2H, d, J=8.7Hz)

(114) N- [l- (4-methoxyphenyl) -3- (3 -fluorophenylthio) -2- propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 114".)

¹ H-NMR(CDCl ₃ )δ(ppm) :3.85 (3H,s) , 6.26 (IH, d, J=15.6Hz) , 6.70~ 7.35(12H,m) , 7.66 (2H, d, J=8.7Hz)

(115) N- [l- (4-methoxyphenyl) -3- (4-fluorophenylthio) -2-

property Ii dene] aniline (Hereinafter, this compound is referred to as "present compound 115".)

¹ H-NMR(CDCl ₃ )δ(ppm) :3.85 (3H,s) , 6.05 (IH, d, J= 15.6Hz) , 6.70~

7.33 (12H,m) ,7.63 (2H, d, J=8.8Hz)

(116) N- [l- (4-methoxyphenyl) -3- (2-chlorophenylthio) -2- propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 116" . )

¹ H-NMR(CDCl ₃ )δ(ppm) :3.86(3H,s),6.20 (IH, d, J=15.4Hz) , 6.67~

7.40 (12H,m) ,7.58~7.70(2H,m)

(117) N- [l- (4-methoxyphenyl) -3- (3-chlorophenylthio) -2- propenylidene) aniline (Hereinafter, this compound is referred to as "present compound 117" . )

¹ H-NMR(CDCl ₃ )δ(ppm) : 3.85 (3H, s) , 6.23 (IH, d, J=15.4Hz) ,6.60~ 7.40 (12H,m) ,7.65 (2H, d, J=8.7Hz)

(118) N- Cl- (4-methoxyphenyl) -3- (4-chlorophenylthio) -2- propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 118" . )

¹ H-NMR(CDCl ₃ )δ(ppm) :3.85 (3H,s) ,6.15 (IH, d, J=15.6Hz) ,6.65~ 7.70 (14H,m)

(119) N- Cl- (4-methoxyphenyl) -3- (2-bromophenylthio) -2- propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 119" . )

¹ H-NMR(CDCl ₃ )δ(ppm) : 3.85 (IH, s) , 6.22 (IH, d, J=15.6Hz) ,6.65~ 7.35 (12H,m) ,7.68 (2H, d, J=8.7Hz)

(120) N- Cl- (4-methoxyphenyl) 3- (3-bromophenylthio) -2-

propenylidene) aniline (Hereinafter, this compound is referred to as "present compound 120".)

¹ H-NMR(CDCl ₃ ) δ(ppm) :3.85 (3H,s) ,6.24 (IH, d, J=15.8Hz) ,6.60~ 7.48 (12H,m) ,7.67 (2H, d, J=9. OHz)

(121) N- [l- (4-methoxyphenyl) -3- (4-bromophenylthio) -2- propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 121" . )

¹ H-NMR(CDCl ₃ )δ(ppm) : 3.86 (2H,s) , 3.88(lH,s), 6.17 (0.7H, d, J=15.4Hz), 6.30—7.90 (14.3H,m)

(122) N- [l- (4-methoxyphenyl) -3- (3- trifluoromethylphenylthio) -2 -propenylidene) aniline (Hereinafter, this compound is referred to as "present compound 122" .)

¹ H-NMR(CDCl ₃ )O(PPm) 6.27 (IH, d, J=15.6Hz) , 6.63~ 7.70 (14H,m)

(123) N- Cl- (4-methoxyphenyl) -3- (2-methylphenylthio) -2- propenylidene) aniline (Hereinafter, this compound is referred to as "present compound 123" . ) 1H-NMR(CDCl ₃ ) δ (ppm) :2.32(3H,s), 3.85(3H,s),

5.95 (IH, d, J=15.4Hz) , 6.65~7.38 (12H,m) ,7.63 (2H, d, J=8.7Hz)

(124) N- Cl- (4-methoxyphenyl) -3- (3 -methylphenylthio) -2- propenylidene) aniline (Hereinafter, this compound is referred to as "present compound 124" .)

¹ H-NMR(CDCl ₃ )δ (ppm) :2.39 (3H,s) , 3.85(3H,s), 6.19 (IH, d, J=15.5Hz), 6.65 — 7.35 (12H,m) , 7.65 (2H, d, J=9.2Hz)

(125) N- [l- (4-methoxyphenyl) -3- (4-methylphenylthio) -2- propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 125" . ) 1H-NMR(CDCl ₃ ) δ (ppm) :2.31 (3H,br) ,3.85 (3H,s) ,

6.11 (IH, d, J=15.8Hz) , 6.55 — 7.40 (12H,m) ,7.63 (2H, d, J=8.7Hz)

(126) N- [l- (4-methoxyphenyl) -3- (2, 4-dimethylphenylthio) -2- propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 126" . )

¹ H-NMR(CDCl ₃ )δ(ppm) : 2.27 (3H, s) , 2.87 (3H, s) , 3.85 (3H, s) , 5.82 (IH, d, J=15.5Hz) ,6.70 —7.49 (12H,m) ,7.62 (2H, d, J=8.7Hz)

(127) N- [l- (4-methoxyphenyl) -3- (3 -methoxyphenylthio) -2- propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 127" .) 1H-NMR(CDCl ₃ )δ(ppm) :3.77(3H,s),3.85(3H,s),

6.24 (lH,d, J=15.8Hz) , 6.65~ 7.45 (12H,m) ,7.66 (2H, d, J=8.7Hz)

(128) N- [l- (4-methoxyphenyl) -3- (4 -methoxyphenylthio) -2- propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 128".) 1H-NMR(CDCl ₃ ) δ (ppm) :3.79(3H,s),3.85(3H,s), 5.98 ( IH, d, J=15.6Hz), 6.54—7.67 (14H,m)

(129) N- Cl- (4-methoxyphenyl) -3- (2, 4-dichlorophenylthio) -2- propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 129" . )

¹ H-NMR(CDCl ₃ )δ(ppm) : 3.86 (1.5H, s) , 3.88 (1.5H, s) , 6.13 (0.5H,d, J=15.6Hz), 6.50—7.75 (13.5H, m)

(130) N- [l- (4-methoxyphenyl) -3- (3 , 5-dichlorophenylthio) -2- propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 130".)

¹ H-NMR(CDCl ₃ )δ(ppm) :3.87(3H,s),6.30 (IH, d, J=15.8Hz) ,6.50~ 7.43(llH,m), 7.67(2H,br)

(131) N- Cl- (4-methoxyphenyl) -3- (4-nitrophenylthio) -2- propenylidene) aniline (Hereinafter, this compound is referred to as "present compound 131".)

¹ H-NMR(CDCl ₃ ) δ (ppm) : 6.45—7.17 (6H,m) , 7.20—7.73 (5H,m) ,7.88— 8.24 (4H,m)

(132) N- Cl- (2-methylphenyl) -3- (3-fluorophenylthio) -2- propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 132".)

¹ H-NMR(CDCl ₃ )δ(ppm) : 2.09 (2H, s) , 2.39 (IH, s) , 6.32 (0.7H, m) , 6.58 —7.48 (14.3H,m)

(133) N- Cl- (2-methylphenyl) -3- (4-fluorophenylthio) -2- propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 133" .)

¹ H-NMR(CDCl ₃ )δ (ppm) : 2.08 (2H,s) , 2.38(lH,s), 6.12—6.43 (0.7H,m), 6.52 —7.48 (14.3H,m)

(134) N- Cl- (2-methylphenyl) -3- (2-chlorophenylthio) -2- propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 134" .)

¹ H-NMR(CDCl ₃ ) δ (ppm) :2.10(2H,s),2.39(lH,s),6.23~6.67(lH,m), 6.83 —7.48 (14H,m)

(135) N- [l- (2-methylphenyl) -3- (3-chlorophenylthio) -2- propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 135" . )

¹ H-NMR(CDCl ₃ )δ(ppm) :2.09(2H,s),2.39(lH,s),6.30~6.67(3H,m), 6.93 —7.43 (12H,m)

(136) N- Cl- (2-methylphenyl) -3- (4-chlorophenylthio) -2- propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 136".) 1H-NMR(CDCl ₃ ) δ (ppm) :2.08(2H,s),2.38(lH,s), 6.22—6.66

(3H,m) , 6.75—7.58 (12H,m)

(137) N- Cl- (2-methylphenyl) 3- (3 -bromophenylthio) -2- propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 137" . )

¹ H-NMR(CDCl ₃ ) δ (ppm) :2.08(2H,s),2.38(lH,s),6.22~6.66 (3H,m) , 6.75—7.58 (12H,m)

(138) N- Cl- (2-methylphenyl) -3- (4 -bromophenylthio) -2- propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 138".)

¹ H-NMR(CDCl ₃ ) δ (ppm) :2.08(2H,s),2.38(lH,s),6.22—6.65(3H,m), 6.74—7.53 (12H,m)

(139) N- Cl- (2-methylphenyl) -3- (2-methylphenylthio) -2- propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 139".)

¹ H-NMR(CDCl ₃ )δ(ppm) : 2.06—2.46 (6H,m) , 6.03—6.65 (3H,m) , 6.77— 7.46 (12H,m)

(140) N- Cl- (2-methylphenyl) -3- (3-methylphenylthio) -2- propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 140" .)

¹ H-NMR(CDCl ₃ ) δ (ppm) :2.07—2.48(6H,m) , 6.27— 6.70 (3H,m) ,6.82 — 7.38 (12H,m)

(141) N- [l- (2-methylphenyl) -3- (4 -methylphenylthio) -2- propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 141" . )

¹ H-NMR(CDCl ₃ ) δ (ppm) :2.06—2.48(6H,m),6.18—6.65(3H,m),6.82— 7.36 (12H,m)

(142) N- [l- (2-methylphenyl) -3- (3- trifluoromethylphenylthio) -2-propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 142" .)

¹ H-NMR(CDCl ₃ ) δ (ppm) : 2.09(2H,s), 2.39(lH,m), 6.30~ 6.67 (3H,m) , 6.82— 7.65 (12H,m)

(143) N- Cl- (2-methylphenyl) -3- (4- trifluoromethylphenylthio) -2-propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 143" .)

¹ H-NMR(CDCl ₃ )δ(ppm) : 2.09 (2H, s) , 2.39 (lH,m) , 6.35~6.73 (3H,m) , 6.83 —7.75 (12H,m)

(144) N- Cl- (2-methylphenyl) -3- (3 -methoxyphenylthio) -2- propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 144" . )

¹ H-NMR(CDCl ₃ ) δ (ppm) :2.08(2H,s),2.38(lH,m),3.75(2H,s), 3.79 (IH, s), 6.32~6.72 (3H,m), 6.75~7.36 (12H,m)

(145) N- [l- (2-methylphenyl) -3- (4-methoxyphenylthio) -2- propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 145" .)

¹ H-NMR(CDCl ₃ ) δ (ppm) :2.08(2H,s),2.37(lH,m),6.08~6.65(3H,m), 6.75—7.55 (12H,m)

(146) N- [l- (2-methylphenyl) -3- (3, 5-dichlorophenylthio) -2- propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 146" .)

¹ H-NMR(CDCl ₃ ) δ (ppm) :2.08(2H,s),2.39(lH,m),6.33~6.68 (3H,m) , 6.84—7.42 (12H,m)

(147) N- Cl- (3-methoxyphenyl) -3- (3-fluorophenylthio) -2- propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 147" . )

¹ H-NMR(CDCl ₃ )δ(ppm) : 3.66 (0.6H, s) , 3.86 (2.4H, s) , 6.27(0.8H,d, J=15.6Hz), 6.52 —7.39 (14.2H,m)

(148) N- Cl- (3-methoxyphenyl) -3- (4-fluorophenylthio) -2- propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 148".)

¹ H-NMR(CDCl ₃ ) δ (ppm) :3.65(0.6H,s) ,3.86(2.4H,s) , 6.06(0.8H,d, J=15.5Hz), 6.34 —7.38 (14.2H,m)

(149) N- Cl- (3-methoxyphenyl) -3- (2-chlorophenylthio) -2- propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 149" .)

¹ H-NMR(CDCl ₃ ) δ (ppm) :3.65(0.6H,s),3.87(2.4H,s), 6.20(0.8H,d, J=15.6Hz), 6.49—7.39(14.2H,m)

(150) N- [l- (3-methoxyphenyl) -3- (3-chlorophenylthio) -2- propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 150".)

¹ H-NMR(CDCl ₃ ) δ (ppm) :3.67(0.6H,s),3.87(2.4H,s), 6.25(0.8H,d, J=15.6Hz), 6.51—7.55(14.2H,m)

(151) N- Cl- (3-methoxyphenyl) -3- (4-chlorophenylthio) -2- propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 151" . )

¹ H-NMR(CDCl ₃ )O(PPm)IS-SS(CeH ₇ S), 3.86 (2.4H, s) , 6.15(0.8H, d, J=15.6Hz), 6.43—7.50(14.2H,m)

(152) N- Cl- (3-methoxyphenyl) 3- (3-bromophenylthio) -2- propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 152" . )

¹ H-NMR(CDCl ₃ )O(PPm): 3.66 (0.6H, s) , 3.87 (2.4H, s) , 6.24(0.8H, d,J=15.6Hz), 6.51—7.68(14.2H,m)

(153) N- Cl- (3-methoxyphenyl) -3- (4-bromophenylthio) -2- propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 153" . ) 1H-NMR(CDCl ₃ ) δ (ppm) : 3.65 (0.6H, s) , 3.86 (2.4H, s) , 6.17(0.8H, d, J=15.6Hz), 6.45—7.53 (14.2H,m)

(154) N- Cl- (3-methoxyphenyl) -3- (2-methylphenylthio) -2- propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 154".)

¹ H-NMR(CDCl ₃ )δ (ppm) :2.32(2.4H,s),2.47(0.6H,s), 3.65(0.6H,s), 3.86(2.4H,s),5.96 (0.8H, d, J=15.4Hz) , 6.28 (0.2H,d, J=15.4Hz) , 6.54~7.37 (14H,m)

(155) N- [l- (3-methoxyphenyl) -3- (3-methylphenylthio) -2- propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 155" . ) 1H-NMR(CDCl ₃ ) δ (ppm) :2.29 (2.4H,s) , 2.36 ( 0.6H, s) ,

3.65 (0.6H,s) , 3.85 (2.4H,s) , 6.20 (0.8H, d, J=15.6Hz) , 6.48 (0.2H,d, J=15.6Hz) , 6.65~7.48 (14H,m)

(156) N- [l- (3-methoxyphenyl) -3- (4 -methylphenylthio) -2- propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 156" . ) 1H-NMR(CDCl ₃ ) δ (ppm) : 2.31 (2.4H, s) , 2.36 (0.6H, s) , 3.65(0.6H,s), 3.85 (2.4H,s) ,6.12 (0.8H, d, J=15.6Hz) ,

6.40 (0.2H,d, J=15.6Hz) , 6.54~7.48 (14H,m)

(157) N- [l- (3-methoxyphenyl) -3- (3- trifluoromethylphenylthio) -2-propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 157" .)

¹ H-NMR(CDCl ₃ ) δ (ppm) : 3.66 (0.6H, s) , 3.86 (2.4H, s) , 6.26 (0.8H,d, J=15.6Hz) , 6.54~7.75 (14.2H, m)

(158) N- [l- (3-methoxyphenyl) -3- (4- trifluoromethylphenylthio) -2-propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 158" . )

¹ H-NMR(CDCl ₃ ) δ (pptn) : 3.66 (0.6H, s) , 3.87 (2.4H, s) , 6.29(0.8H, d, J=15.6Hz), 6.54 —7.65 (14.2H,m)

(159) N- [l- (3-methoxyphenyl) -3- (3-methoxyphenylthio) -2- propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 159".) 1H-NMR(CDCl ₃ ) δ (pptn) :3.65 (0.6H, s) , 3.77 (2.4H, s) , 3.81(0.6H,s) , 3.85 (2.4H,s) , 6.27 (0.8H, d, J=15.6Hz) , 6.47— 7.37 (14.2H,m)

(160) N- (l- (3-methoxyphenyl) -3- (4-methoxyphenylthio) -2- propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 160" . ) 1H-NMR(CDCl ₃ ) δ (ppm) :3.64 (0.6H,s) , 3.78 (2.4H,s) ,

3.82 (0.6H,s) , 3.85 (2.4H,s) , 5.99 ( 0.8H ₇ d, J=15.4Hz) , 6.28 (0.2H,d, J=15.4Hz) , 6.53 —7.46 (14.2H,m)

(161) N- [l- (3-methoxyphenyl) -3- (3, 5-dichlorophenylthio) -2- propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 161" . )

¹ H-NMR(CDCl ₃ ) δ(ppm) :3.87(3H,s), 6.30 (IH, d, J=15.4Hz) ,6.53 — 7.57 (14H,m)

(162) N- [l- (2-chlorophenyl) -3- (3-fluorophenylthio) -2- propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 162" . )

¹ H-NMR(CDCl ₃ ) δ (ppm) : 6.35 (0.4H, d, J=15.4Hz) , 6.62(0.6H, d, J=15.4Hz), 6.69—7.46 (14H,m)

(163) N- Cl- (2-chlorophenyl) -3- (4 -fluorophenylthio) -2-

propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 163".)

¹ H-NMR(CDCl ₃ )O(PPm): 6.16 ( 0.4H, d, J=15.4Hz) , 6.40(0.6H, d, J=15.4Hz) , 6.56 (0.6H, d, J=6.6Hz) ,6.59 (0.4H, d, J=6.6Hz) ,6.67 —7.49 (13H,m)

(164) N- [l- (2-chlorophenyl) -3- (2-chlorophenγlthio) -2- propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 164" . )

¹ H-NMR(CDCl ₃ )δ(ppm) :6.29 (0.5H, d, J=15.4Hz) , 6.59(0.5H, d, J=15.4Hz), 6.68~7.61(14H,m)

(165) N- [l- (2-chlorophenyl) -3- (3-chlorophenylthio) -2- propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 165" . )

¹ H-NMR(CDCl ₃ ) δ (ppm) :6.33 (0.4H, d, J=15.4Hz) ,6.61(0.6H,d, J=15.4Hz), 6.69—7.45 (14H,m)

(166) N- Cl- (2-chlorophenyl) -3- (4-chlorophenylthio) -2- propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 167" . ) 1H-NMR(CDCl ₃ ) δ(ppm) :6.23~6.62(lH,m)6.66~7.48 (14H,m)

(167) N- Cl- (2-chlorophenyl) 3- (3-bromophenylthio) -2- propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 167" . )

¹ H-NMR(CDCl ₃ )δ(ppm) :6.33 (0.4H, d, J=15.4Hz) , 6.60 (0.6H,d, J=15.4Hz), 6.69~7.58(14H,m) (168) N- Cl- (2-chlorophenyl) -3- (4-bromophenylthio) -2-

propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 168".)

¹ H-NMR(CDCl ₃ )δ(ppm) : 6.23~6.62 (lH,m) , 6.68—7.51 (14H,m)

(169) N- [l- (2-chlorophenyl) -3- (2-methylphenylthio) -2- propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 169" . )

¹ H-NMR(CDCl ₃ )δ(ppm) : 2.32 (1.2H, s) , 2.45 (1.8H, s) , 6.06 (0.4H,d, J=15.4Hz) ,6.28 (0.6H, d, J=15.4Hz) , 6.55 (0.6H, d, J=15.2Hz) ,6.59( 0.4H,d, J=15.2Hz) ,6.67—7.46 (13H,m)

(170) N- [l- (2-chlorophenyl) -3- (3-methylphenylthio) -2- propenylidene) aniline (Hereinafter, this compound is referred to as "present compound 170" . )

¹ H-NMR(CDCl ₃ ) δ (ppm) :2.31(1.4H,s),2.35(1.6H,s), 6.30 (0.4H, d, J=15.4Hz) ,6.51(0.6H,d, J=15.7Hz) ,6.63 (0.6H, d, J=15.4Hz) , 6.66 (0.4H,d, J=15.4Hz) ,6.70—7.43 (13H,m)

(171) N- Cl- (2-chlorophenyl) -3- (4-methylphenylthio) -2- propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 171".)

¹ H-NMR(CDCl ₃ )δ(ppm) : 2.34 (1.2H, s) , 2.35 (1.8H, s) , 6.22 (0.4H,d, J=15.4Hz) ,6.43 (0.6H, d, J=15.4Hz) ,6.60 (0.6H, d, J=15.4Hz) , 6.64 ( 0.4H,d, J=15.4Hz) ,6.67—7.42 (13H,m)

(172) N- Cl- (2-chlorophenyl) -3- (3- trifluoromethylphenylthio) -2-propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 172" .)

¹ H-NMR ( CDCl ₃ ) δ (ppm) : 6 . 34 ( 0 . 4H , d , J= 15 . 4Hz ) , 6 . 60 ~ 6 . 64 ( 1 . 6H , m) , 6 . 70 ~ 7 . 66 ( 13H , m)

(173) N- [l- (2-chlorophenyl) -3- (4- trifluoromethylphenylthio) -2-propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 173" .)

¹ H-NMR(CDCl ₃ )δ(ppm) : 6.39 (0.4H, d, J=15.4Hz) , 6.51 (0.6H, d, J=15.4Hz) , 6.64 (0.4H, d, J=15.4Hz) , 6.68~7.63 (13.6H, m)

(174) N- Cl- (2-chlorophenyl) -3- (3 -methoxyphenylthio) -2- propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 174" .)

¹ H-NMR(CDCl ₃ )δ (ppm) :3.80(3H,s),6.36 (IH, d, J=15.7Hz) , 6.60~ 7.43 (14H,m)

(175) N- Cl- (2-chlorophenyl) -3- (4 -methoxyphenylthio) -2- propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 175" . )

¹ H-NMR(CDCl ₃ ) δ (ppm) :3.78(0.6H,s) , 3.80(2.4H,s) ,6.11(0.4H,d, J=15.4Hz) , 6.32 (0.6H, d, J=15.4Hz) , 6.70 ~7.49 (14H,m)

(176) N- Cl- (2-chlorophenyl) -3- (3, 5-dichlorophenylthio) -2- propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 176" . )

¹ H-NMR(CDCl ₃ ) δ (ppm) :6.37 (0.4H, d, J=15.6Hz) ,6.54 (0.6H,d, J=15.6Hz) ,6.56 (0.4H, d, J=15.6Hz) ,6.66 (0.6H, d, J=15.6Hz) ,6.70 ~7.49(12H,m)

(177) N- Cl- (4-nitrophenyl) -3- (3 -fluorophenylthio) -2-

propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 177" . )

¹ H-NMR(CDCl ₃ ) δ (ppm) :6.25 (0.6H, d, J=15.6Hz) ,β.55(0.4H,d, J=15.6Hz), 6.67—7.35 (1OH, m) 7.84 (2H, d, J=8.8Hz) , 8.32 (2H,d, J=8.8Hz)

(178) N- [l- (4-nitrophenyl) -3- (4-fluorophenylthio) -2- propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 178" . )

¹ H-NMR(CDCl ₃ ) δ (ppm) :6.07 (0.8H, d, J=15.4Hz) ,6.37(0.2H,d, J=15.4Hz) , 6.79~7.65 (1OH, m), 7.82 (2H, d, J=8.8Hz) , 8.30 (2H,d, J=8.8Hz)

(179) N- [l- (4-nitrophenyl) -3- (2-chlorophenylthio) -2- propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 179".)

¹ H-NMR(CDCl ₃ )δ(ppm) : 6.17 (0.8H, d, J=15.7Hz) , 6.49 (0.2H, d, J=15.7Hz) ,6.71 (0.2H,d, J=15.7Hz) ,6.80 (0.8H, d, J=15.7Hz) ,6.83 —7.60 (9H,m) , 7.85 (2H, d, J=8.8Hz) ,8.30 (2H, d, J=8.8Hz)

(180) N- Cl- (4-nitrophenyl) -3- (3 -chlorophenylthio) -2- propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 180".)

¹ H-NMR(CDCl ₃ )δ(ppm) : 6.24 (0.8H, d, J=15.6Hz) ,6.52 (0.2H,d, J=15.6Hz), 6.81—7.65 (1OH, m) , 7.85 (2H, d, J=8.8Hz) , 8.32(2H,d, J=8.8Hz)

(181) N- Cl- (4-nitrophenyl) -3- (4 -chlorophenylthio) -2- propenylidene] aniline (Hereinafter, this compound is

referred to as "present compound 181".)

¹ H-NMR(CDCl ₃ ) δ (ppm) : 6.15 (0.8H, d, J=15.6Hz) ,6.45(0.2H,d,

J=15.6Hz), 6.74—7.45 (1OH, m) ,7.83 (2H,d,J=8.8Hz) , 8.30(2H,d,

J=8.8Hz)

(182) N- [l- (4-nitrophenyl) 3- (3-bromophenylthio) -2- propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 182".) 1H-NMR(CDCl ₃ )δ(ppm) :6.24 (IH, d, J=15.6Hz) , 6.83 (IH, d, J=15.6Hz), 7.07—7.65 (9H,m) , 7.83 (2H, d, J=8.8Hz) , 8.31(2H,d, J=8.8Hz)

(183) N- [l- (4-nitrophenyl) -3- (4-bromophenylthio) -2- propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 183".)

¹ H-NMR(CDCl ₃ ) δ(ppm) : 6.17 (0.8H, d, J=15.7Hz) ,6.47(0.2H,d, J=15.7Hz), 6.50 —7.55 (14H,m) ,7.82 (2H,d,J=8.8Hz) , 8.30(2H,d, J=8.8Hz)

(184) N- Cl- (4-nitrophenyl) -3- (2-methylphenylthio) -2- propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 184" . )

¹ H-NMR(CDCl ₃ )δ (ppm) : 2.33 (2.4H,s) , 2.46 (0.6H, s) , 5.93 — 6.85 (3H,m) ,7.06—7.32 (8H,m) ,7.78—8.33 (4H,m)

(185) N- Cl- (4-nitrophenyl) -3- (3-methylphenylthio) -2- propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 185".) 1H-NMR(CDCl ₃ )δ(ppm) :2.29(3H,s) , 6.21 (IH, d, J=15.7Hz) ,

6 . 88 ( IH, d, J=15 . 7Hz ) , 6 . 97 ~ 7 . 30 ( 10H , m) , 7 . 83 ( 2H, d , J=8 . 8Hz ) , 8 . 29 ( 2H , d, J=8 . 8Hz )

(186) N- Cl- (4-nitrophenyl) -3- (4-methylphenylthio) -2- propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 186" . )

¹ H-NMR(CDCl ₃ ) δ (ppm) :2.30—2.38(3H,m)6.10~6.88(3H,m),6.96~ 7.45 (8H,m) ,7.82 (2H, d, J=8.8Hz) ,8.29 (2H, d, J=8.8Hz)

(187) N- [l- (4-nitrophenyl) -3- (3- trifluoromethylphenylthio) -2-propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 187" .)

¹ H-NMR(CDCl ₃ ) δ (ppm) :6.24 (IH, d, J=15".7Hz) , 6.81~6.86(3H,m), 7.07—7.75 (7H,m) , 7.85 (2H, d, J=8.8Hz) , 8.31 (2H, d, J=8.8Hz)

(188) N- Cl- (4-nitrophenyl) -3- (4- trifluoromethylphenylthio) -2-propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 188" .)

¹ H-NMR(CDCl ₃ ) δ (ppm) :6.25~6.89(4H,m),7.08~7.65(7H,m), 7.85 (2H,d, J=8.8Hz) , 8.32 (2H, d, J=8.8Hz)

(189) N- Cl- (4-nitrophenyl) -3- (3-methoxyphenylthio) -2- propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 189".)

¹ H-NMR(CDCl ₃ )δ(ppm) : 3.73 (3H, s) , 6.26 (IH, d, J=15.9Hz) ,6.53— 7.55 (1OH, m) , 7.77~8.33 (4H,m)

(190) N- Cl- (4-nitrophenyl) -3- (4-methoxyphenylthio) -2-

propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 190" . ) 1H-NMR(CDCl ₃ ) δ (ppm) :3.82(2.4H,s),3.83(0.6H,s),6.00~ 6.38 (IH, m) ,6.52—7.50 (10H,m) , 7.75~8.32 (4H,m)

(191) N- [l- (4-nitrophenyl) -3- (3 , 5-dichlorophenylthio) -2- propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 191" . )

¹ H-NMR(CDCl ₃ )δ (ppm) :6.28 (IH, d, J=15.7Hz) ,

6.79 (IH, d, J=15.7Hz) , 6.85 (2H, d, J=8.5Hz) , 7.15~

7.45 (6H,m) ,7.85 (2H,d,J=8.8Hz) , 8.32(2H, d, J=8.8Hz)

(192) N- [l- (4-phenylphenyl) -3- (3 -fluorophenylthio) -2- propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 192" . )

¹ H-NMR(CDCl ₃ )δ (ppm) :6.30 (IH, d, J=15.4Hz) , 6.78~7.82 (19H,m)

(193) N- Cl- (4-phenylphenyl) -3- (4 -fluorophenylthio) -2- propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 193" . )

¹ H-NMR(CDCl ₃ ) δ (ppm) :6.10 (IH, d, J=15.4Hz) ,6.78~7.78 (19H,m)

(194) N- Cl- (4-phenylphenyl) -3- (2-chlorophenylthio) -2- propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 194" . )

¹ H-NMR(CDCl ₃ )δ(ppm) :6.25 (IH, d, J=15.6Hz) ,6.82—7.80 (19H,m)

(195) N- [l- (4-phenylphenyl) -3- (3 -chlorophenylthio) -2- propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 195" . )

¹ H-NMR(CDCl ₃ ) δ (ppm) :6.28 (IH, d, J=15.6Hz) ,6.79—7.83(19H,m)

(196) N- [l- (4-phenylphenyl) -3- (4-chlorophenylthio) -2- propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 196".)

¹ H-NMR(CDCl ₃ )δ(ppm) : 6.20 (IH, d, J=15.9Hz) , 6.77—7.80 (19H,m)

(197) N- [l- (4-phenylphenyl) 3- (3 -bromophenylthio) -2- propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 197" . )

¹ H-NMR(CDCl ₃ )δ(ppm) :6.29 (IH, d, J=15.4Hz) ,6.79—7.82 (19H,m)

(198) N- [l- (4-phenylphenyl) -3- (4 -bromophenylthio) -2- propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 198" . )

¹ H-NMR(CDCl ₃ ) δ (ppm) :6.22 (IH, d, J=15.6Hz) ,6.78 —7.80 (19H,m)

(199) N- [l- (4-phenylphenyl) -3- (2-methylphenylthio) -2- propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 199".)

¹ H-NMR(CDCl ₃ ) δ (ppm) :2.13 (2H, s) , 2.17 (IH, s) , 6.00(0.7H,d, J=15.6Hz) , 6.32 (0.5H, d, J=15.6Hz) ,6.78—7.77 (19H,m)

(200) N- [l- (4-phenylphenyl) -3- (3-methylphenylthio) -2- propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 200" . )

¹ H-NMR(CDCl ₃ )δ(ppm) : 2.23 (2H, s) , 2.29 (IH, s) , 6.14 (0.7H,d, J=15.9Hz) , 6.52 (0.3H, d, J=15.9Hz) ,6.80~7.78 (19H,m)

(201) N- [l- (4-phenylphenyl) -3- (4-methylphenylthio) -2- propenylidene] aniline (Hereinafter, this compound is

referred to as "present compound 201" .)

¹ H-NMR(CDCl ₃ )δ(ppm) : 2.21 (2H,s) , 2.22(lH,s) , 6.17 (0.7H, d,

J=15.5Hz), 6.45(0.3H,d, J=15.5Hz) , 6.80~7.77 (19H,m)

(202) N- [l- (4-phenylphenyl) -3- (3- trifluoromethylphenylthio) -2-propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 202" .) 1H-NMR(CDCl ₃ ) δ(ppm) : 6.31 (IH, d, J=15.5Hz) ,6.78—7.78 (19H,m)

(203) N- Cl- (4-phenylphenyl) -3- (4- trifluoromethylphenylthio) -2-propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 203".) 1H-NMR(CDCl ₃ ) δ (ppm) :6.35 (IH, d, J=15.6Hz) ,6.78—7.78(19H,m)

(204) N- [l- (4-phenylphenyl) -3- (3-methoxyphenylthio) -2- propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 204" .)

¹ H-NMR(CDCl ₃ )δ(ppm) : 3.67 (1.5H, s) , 3.77 (1.5H, s) , 6.30 (0.5H,d, J=15.6Hz) ,6.70—7.78(19.5H,m)

(205) N- Cl- (4-phenylphenyl) -3- (4-methoxyphenylthio) -2- propenylidene] aniline (Hereinafter, this compound is referred to as "present compound 205".)

¹ H-NMR(CDCl ₃ ) δ(ppm) :3.78 (3H,brs) ,6.05 (0.5H, d, J=15.4Hz) ,6.52 —7.76 (19.5H,m)

(206) N- Cl- (4-phenylphenyl) -3- (3, 5-dichlorophenylthio) -2- propenylidene] aniline (Hereinafter, this compound is

referred to as "present compound 206".)

¹ H-NMR(CDCl ₃ ) δ (ppm) :6.34 (IH, d, J=15.4Hz) ,β.79~7.88(18H,m)

Production Example 207

Production of (207) N- Cl- (4-trifluoromethylphenyl ) -3- (4- fluorophenylthio) -2-propenylidene] 4-chloroaniline

(Hereinafter, this compound is referred to as "present compound 207".)

To methanol solution (10 ml) of N- [l- (4- trifluoromethylphenyl) -3-trimethylsilyl-2-propenylidene] ] -4-chloroaniline (0.7g), potassium carbonate (catalytic amount) was added and stirred for one hour. Then, methanol solution (2 ml) containing 0.22 g of 4-fluorothiophenol was dropped under ice cool, and stirred for 14 hours at room temperature. The reaction mixture was concentrated under reduced pressure and the resultant residue was subjected to silica gel column chromatography (hexane : ethyl acetate = 10:1) to obtain the present compound 207 (0.48 g) . m.p. :85~93 ⁰ C

¹ H-NMR(CDCl ₃ )δ(ppm) : 5.99 (0.8H, d, J=15.7Hz) ,6.32 (0.2H,d, J=15.7Hz) ,6.49 (0.4H, d, J=8.5Hz) ,6.73 (1.6H, d, J=8.5Hz) ,6.76 (0. 2H,d, J=15.5Hz) ,6.86 (0.8H, d, J=15.5Hz) , 6.99~ 7.54 (6H,τn) , 7.68 —7.76 (4H,m)

Production Examples 208 to 261 The following compounds were produced according to the

methods of Production Example 207.

(208) N- [l- (4-trifluoromethylphenyl) 3- (4- methylphenylthio) -2-propenylidene] -4-chloroaniline

(Hereinafter, this compound is referred to as "present compound 208" .) m.p. :104~107 ⁰ C

¹ H-NMR(CDCl ₃ )O(PPm): 2.32(lH,s), 2.37(2H,s), 6.13 (0.3H,d,

J=15.6Hz), 6.39(0.7H,d, J=15.6Hz), 6.68~7.32 (9H,m) , 7.43(1.4H,d, J=8.0Hz), 7.54(1.4H,d, J=8.2Hz), 7.72(0.6H,d, J=8.2Hz), 7.98 (0.6H,d,J=8. OHz)

(209) N- [l- (4-trifluoromethylphenyl) -3- (4- fluorophenylthio) -2-propenylidene] -4—methylaniline

(Hereinafter, this compound is referred to as "present compound 209".) m.p. :105~108 °C

¹ H-NMR(CDCl ₃ )δ(ppm) : 2.36 (3H _^ s) , 6.09 (IH, d, J=15.6Hz) ,

6.70(2.4H, d, J=8.0Hz), 6.81 (IH, d, J=15.6Hz), 6.88(0.6H, d

J=8.0Hz), 6.96~7.53 (5H,m) , 7.68~7.76 (4H,m)

(210) N- Cl- (4-trifluoromethylphenyl) -3- (4- methylphenylthio) -2-propenylidene] -4— methylaniline

(Hereinafter, this compound is referred to as "present compound 210" .) m.p. :117~119 °C

¹ H-NMR(CDCl ₃ )δ(ppm) : 2.19 (0.6H, s) , 2.32 (2.4H, s) , 2.36 (3H,br) ,

6.19 (0.8H,d, J=15.6Hz) ,6.40 (0.2H, d, J=15.6Hz) ,6.45 (0.4H,d, J=8

.2Hz) ,6.72 (0.2H,d, J=15.7Hz) ,6.73 (1.6H, d, J=8.2Hz) ,6.86 (0.8H, d, J=15.7Hz) , 7.08 — 7.51 (6H,m) , 7.67~7.76 (4H,m)

(211) N- [l- (4-trifluoromethylphenyl) -3- (4- fluorophenylthio) -2-propenylidene] -4-bromoaniline (Hereinafter, this compound is referred to as "present compound 211" .) m.p. :83~87 °C

¹ H-NMR(CDCl ₃ )δ(ppm) : 2.19 (0.6H, s) , 2.32 (2.4H, s) , 2.36 (3H,br) , 6.19 (0.8H,d, J=15.6Hz) ,6.40 (0.2H, d, J=15.6Hz) , 6.45 ( 0.4H, d, J=8 .2Hz) ,6.72 (0.2H,d, J=15.7Hz) ,6.73 (1.6H, d, J=8.2Hz) ,6.86 (0.8H, d, J=15.7Hz) ,7.08 — 7.51 (6H,m) , 7.67 ~ 7.76 (4H, m)

(212) N- Cl- (4-trifluoromethylphenyl) -3- (4- methylphenylthio) -2-propenylidene] -4-bromoaniline

(Hereinafter, this compound is referred to as "present compound 212" .) m.p. :126~129 °C

¹ H-NMR(CDCl ₃ )δ(ppm) : 2.32 (0.5H,s) , 2.37 (2.5H, s) , 5.94(0.8H, d, J=15.6Hz) , 6.37 (0.2H, d, J=15.6Hz) , 6.62~6.93 (3H, m) , 7.11

~7.55(6H,m) , 7.68~7.75 (4H,m)

(213) N- [l- (4-trifluoromethylphenyl) -3- (4- fluorophenylthio) -2-propenylidene] -3-methylaniline

(Hereinafter, this compound is referred to as "present compound 213" .) m.p. :91~94 °C

¹ H-NMR(CDCl ₃ )δ(ppm) : 2.16 (0.5H, s) , 2.34 (2.5H,s) , 6.07(0.8H,d,

J=15.6Hz) ,6.31(0.4H,d, J= 8. OHz) ,6.35 (0.2H ₇ d, J=15.6Hz) ,6.60 (1 .6H,d, J=8.0Hz) ,6.72 (0.2H, d, J= 15.6Hz) ,6.82 (0.8H, d, J=15.6Hz)

(214) N- [l- (4-trifluoromethylphenyl) -3- (4- methylphenylthio) -2~propenylidene] -3-methylaniline

(Hereinafter, this compound is referred to as "present compound 214" .) m.p. :101~103 ⁰ C

¹ H-NMR(CDCl ₃ ) δ (ppm) :2.16(0.5H,s) ,2.32(2.5H,s) ,2.34(2.5H,s) ,

2.37 (0.5H,s) ,6.14 (0.8H, d, J=15.6Hz) ,6.39 (0.2H, d, J=15.6Hz) , 6.

62 (1.6H,d, J=8.7Hz) ,6.75 (0.2H, d, J=15.6Hz) ,6.87 (0.8H, d, J=15.6

Hz) ,6.68 (0.4H,d, J=8.7Hz) , 7.08~7.52 (6H,m) , 7.67~7.76 (4H,m)

(215) N- Cl- (4-trifluoromethylphenyl) -3- (4- fluorophenylthio) -2-propenylidene] -3-chloroaniline (Hereinafter, this compound is referred to as "present compound 215" .) m.p. :105~107 ⁰ C

¹ H-NMR(CDCl ₃ ) δ(ppm) :5.89 (0.8H,d, J=15.5Hz) , 6.31(0.2H,d, J=15.5Hz) ,6.38 (0.2H, d, J=8. OHz) ,6.61 (0.2H, t, J=2.1Hz) , 6.68 (0. 8H,d, J=8.0Hz) ,6.75~6.79(lH,m),6.89 (0.8H, d, J=15.6Hz) ,6.96~ 7.55 (6H,m) ,7.70—7.76 (4H,m)

(216) N- Cl- (4-trifluoromethylphenyl) -3- (4- methylphenylthio) -2-propenylidene] -3-chloroaniline

(Hereinafter, this compound is referred to as "present compound 216".) m.p. :88~90 °C

¹ H-NMR(CDCl ₃ )δ(ppm) : 2.33 (2.5H, s) , 2.37 (0.5H, s) , 5.93 (0.8H,d, J=15.5Hz) , 6.35 (0.2H,d,J=15.5Hz) ,6.38 (0.2H, d, J=8. OHz) ,6.61(0 .2H, t, J=2.0Hz) ,6.68 (0.8H, d, J=8. OHz) ,6.78 (0.8H, t , J=2. OHz) , 6.80 (0.2H,d, J=15.6Hz) , 6.93 (0.8H, d, J=15.6Hz) , 7.03 — 7.54(6H,m), 7.69— 7.75 (4H,m)

(217) N- [l- (4-trifluoromethylphenyl) -3- (4- fluorophenylthio) -2-propenylidene] -4-phenylaniline

(Hereinafter, this compound is referred to as "present compound 217" .) m.p. : 152 —156 °C

¹ H-NMR(CDCl ₃ )δ(ppm) : 6.15 (0.8H, d, J=15.6Hz) , 6.38 (0.2H, d,

J=15.6Hz) ,6.63 (0.4H,d, J=8.5Hz) ,6.76 (0.2H, d, J=15.6Hz) ,6.85 —

7.63 (13.4H,m) ,7.70 — 7.78 (4H,m)

(218) N- Cl- (4-trifluoromethylphenyl) -3- (4- methylphenylthio) -2-propenylidene] -4-phenylaniline

(Hereinafter, this compound is referred to as "present compound 218" .) m.p. :165~169 °C

¹ H-NMR(CDCl ₃ )δ(ppm) : 2.19 (2.4H, s) , 2.37 (0.6H, s) , 6.18 (0.8H, d,

J=15.6Hz) ,6.42 (0.2H, d, J=15.6Hz) ,6.63 (0.4H, d, J=8.2Hz) ,6.79 (0

.2H,d, J=15.6Hz) ,6.88—6.93(2.4H,m) , 7.05—7.54 (llH,m) ,7.69—

7.75 (4H,m)

(219) N- Cl- (4-trifluoromethylphenyl) -3 - (4- f luorophenylthio) -2 -propenylidene] -4- isopropylaniline (Hereinafter, this compound is referred to as "present

compound 219" .) m.p..-110 — 114

¹ H-NMR(CDCl ₃ ) δ(ppm) : 1.13 (IH, d, J=7. IHz) ,1.27 (5H, d, J=7. IHz) ,

2.71 — 2.96 (IH ₇ In) , 6.11 ( 0.8H, d, J=15.5Hz) ,

6.37 (0.2H,d,J=15.6Hz) , 6.48 (0.4H, d, J=8.2Hz) , 6.70(0.2H,d,

J=15.5Hz) , 6.74 (1.6H,d,J=8.2Hz) , 6.82 (0.8H, d, J=15.5Hz) ,

6.91 — 7.52 (6H,m) , 7.68~7.76 (4H,m)

(220) N- [l- (4-trifluoromethylphenyl) -3- (4- methylphenylthio) -2-propenylidene] -4-isopropylaniline

(Hereinafter, this compound is referred to as "present compound 220" .) m.p. :102—106 °C

¹ H-NMR(CDCl ₃ ) δ(ppm) :1.13 (IH, d, J=6.9Hz) ,1.28 (5H, d, J=6.9Hz) ,

2.31(2.6H,s) ,2.36 (0.4H,s) ,2.71—2.96 (IH, m) , 6.24 (0.8H,d,

J=15.5Hz), 6.41 (0.2H,d,J=15.6Hz) , 6.47 (0.3H, d, J=8.2Hz) ,

6.73 (0.2H,d, J=15.5Hz) ,6.78 (1.7H, d, J=8.2Hz) , 6.86 (0.8H, d, J=15

.5Hz) ,6.91—7.51(6H,m),7.67~7.76(4H,m)

(221) N- Cl- (4-trifluoromethylphenyl) -3- (4- fluorophenylthio) -2-propenylidene] -A- trifluoromethylaniline (Hereinafter, this compound is referred to as "present compound 221".) m.p. :96~99 °C

¹ H-NMR(CDCl ₃ )δ(ppm) : 1.13 (IH, d, J=6.9Hz) ,1.28 (5H, d, J=6.9Hz) ,

2.31 (2.6H ₇ s) ,2.36(0.4H ₇ S) ,2.71~ 2.96 (IH, m) , 6.24 (0.8H, d,

J=15.5Hz) , 6.41(0.2H,d, J=15.6Hz) , 6.47 (0.3H, d, J=8.2Hz) ,

6.73 (0.2H,d, J=15.5Hz) ,6.78 (1.7H, d, J=8.2Hz) , 6.86 (0.8H, d, J=15 .5Hz) , 6.91 — 7.51 (6H,m) ,7.67 — 7.76 (4H,m)

(222) N- [l- (4-trifluoromethylphenyl) -3- (4- methylphenylthio) -2-propenylidene] -4- trifluoromethylaniline (Hereinafter, this compound is referred to as "present compound 222" . ) m.p. : 124—128 ⁰ C

¹ H-NMR(CDCl ₃ ) δ (ppm) :2.30(2.6H,s) ,2.37(0.4H,s) ,5.84(0.8H,d,

J=15.6Hz) ,6.36 ( 0.2H, d, J=15.6Hz) ,6.63 (0.3H, d, J=8.2Hz) ,6.82 (0

.2H,d, J=15.6Hz) ,6.85 (1.7H, d, J=8.2Hz) , 6.95 (0.8H, d, J=15.6Hz) ,

7.06 — 7.56 (6H,m) , 7.70 — 7.78 (4H, m)

(223) N- [l- (4-trifluoromethylphenyl) -3- (4- f luorophenylthio) -2-propenylidene] -4-f luoroaniline

(Hereinafter, this compound is referred to as "present compound 223" .) m.p. :91 — 95 ⁰ C

¹ H-NMR(CDCl ₃ ) δ (ppm) : 6.04 (0.8H, d, J=15.6Hz) ,6.34(0.2H,d,

J=15.6Hz) ,6.49 — 6.52 (0.4H,m) ,6.72 — 6.79 (2.8H,m) ,

6.85 (0.8H,d, J=15.6Hz) , 6.98 — 7.54 (5H,m) , 7.69 — 7.76 (4H,m)

(224) N- Cl- (4-trifluoromethylphenyl) -3- (4- methylphenylthio) -2-propenylidene] -4-fluoroaniline

(Hereinafter, this compound is referred to as "present compound 224" .) m.p. :85~88 °C

¹ H-NMR(CDCl ₃ )δ(ppm) : 2.33 (2.4H, s) , 2.37 (0.6H, s) , 6.01 (0.8H,d,

J=15.6Hz) ,6.37 (0.2H, d, J=15.6Hz) ,6.48 — 6.53(0.4H,m),6.73~ 6.79 (1.8H,m) ,6.90 (0.8H, d, J= 15.6Hz) , 6.96—7.53 (6H,m) ,7.68— 7.75 (4H,m)

(225) N- [l- (4-trifluoromethylphenyl) -3- (4- fluorophenylthio) -2-propenylidene] -3-fluoroaniline

(Hereinafter, this compound is referred to as "present compound 225" .) m.p. :94~ 97 ⁰ C

¹ H-NMR(CDCl ₃ ) δ (ppm) :5.94 (0.8H, d, J=15.6Hz) , 6.29—

6.34 (0.4H,m) , 6.49 —6.58 (1.8H,m) , 6.75—6.82 (1.2H, m) ,

6.88 (0.8H,d, J=15.6Hz) , 6.98~7.54 (5H,m), 7.69—7.76 (4H,m)

(226) N- [l- (4-trifluoromethylphenyl) -3- (4- methylphenylthio) -2-propenylidene] -3-fluoroaniline

(Hereinafter, this compound is referred to as "present compound 226" . ) m.p. :87~90 ⁰ C

¹ H-NMR(CDCl ₃ )δ(ppm) : 2.32 (2.5H, s) , 2.37 (0.5H, s) , 5.98 (0.8H,d,

J=15.6Hz) ,6.29— 6.32(0.4H,m),6.35 (0.2H, d, J=15.6Hz) ,6.49—

6.60 (1.8H,m) ,6.75 —6.81 (IH, m) ,6.93 (0.8H, d, J=15.6Hz) ,7.10 —

7.53 (5H,m) ,7.69—7.76 (4H,m)

(227) N- Cl- (4-trifluoromethylphenyl) -3- (4- fluorophenylthio) -2-propenylidene] -3 , 4 -dimethylaniline (Hereinafter, this compound is referred to as "present compound 227" .) m.p. :103~107 °C

¹ H-NMR(CDCl ₃ ) δ (ppm) : 2.06 (0.5H, s) ,2.10 (0.5H,s) ,

2.24 (2.5H,s) , 2.26(2.5H,s) ,6.10 (0.9H, d, J=15.6Hz) ,

6.23 (0.1H,d, J=7.8Hz) , 6.36 (0. IH, d, J= 15.6Hz) ,6.40(0.1H,s) ,6.5

4 (0.9H,d, J=7.8Hz) ,6.59(0.9H,s) ,6.68 (0. IH, d, J=15.6Hz) ,6.80 (0

.9H,d, J=15.6Hz) , 6.94 ~ 7.51 (5H,m) , 7.67~7.75 (4H,m)

(228) N- [l- (4-trifluoromethylphenyl) -3- (4- methylphenylthio) -2-propenylidene) -3 , 4-dimethylaniline

(Hereinafter, this compound is referred to as "present compound 228" .) m.p. :123~127 ⁰ C

¹ H-NMR(CDCl ₃ ) δ (ppm) :2.06(0.5H,s) ,2.09(0.5H,s) ,

2.25(2.5H,s) ,2.26(2.5H,s) ,2.31(2.5H,s) ,2.36(0.5H,s) ,6.19~

6.23(lH,m),6.37~6.41(0.4H,m),6.56~6.63(1.6H,m),

6.71(0.2H,d, J=15.6Hz), 6.84 (0.8H, d, J=15.6Hz) , 7.05~

7.52(5H,m) , 7.67~7.75 (4H,m)

(229) N- [l- (4-trifluoromethylphenyl) -3- (4- fluorophenylthio) -2-propenylidene] -4-methoxyaniline (Hereinafter, this compound is referred to as "present compound 229" .)

¹ H-NMR(CDCl ₃ ) δ(ppm) : 3.74 (2. IH, s) , 3.82 (0.9H, s) , 6.25 (0.3H,d, J=9.9Hz), 6.38 (0.7H,d,J=9.9Hz) ,6.66 (0.3H,d, J=IO.6Hz) , 6.72 —7.97 (12.7H,m)

(230) N- [l- (4-trifluoromethylphenyl) -3- (4- methylphenylthio) -2-propenylidene) -4-methoxyaniline

(Hereinafter, this compound is referred to as "present

compound 230" .) m.p. :114~ 117 ⁰ C

¹ H-NMR(CDCl ₃ )δ(ppm) :2.32(2.4H,s) ,2.36(0.6H,s) ,

3.69(0.6H,s) ,3.85(2.4H,s) ,6.22 (0.8H, d, J=15.6Hz) ,

6.40 (0.2H,d, J=15.6Hz) , 6.49~ 6.52 (0.4H, m) , 6.60 — 6.64

(0.4H,m), 6.72 (0.2H, d, J=15.6Hz) , 6.79~ 6.88 (4H,m) , 7.10 —

7.53 (4H,m) ,7.67 — 7.76 (4H,m)

(231) N- [l- (4-trifluoromethylphenyl) -3- (4- fluorophenylthio) -2-propenylidene] -2-methylaniline

(Hereinafter, this compound is referred to as "present compound 231" .) m.p. :92~94 ⁰ C

¹ H-NMR(CDCl ₃ ) δ (ppm) :2.07 (2.4H, s) , 2.13 (0.6H, s) , 5.91—

5.45 (IH, m) , 6.57~7.30(9H,m),7.44 —7.52(0.8H,m),7.67~

7.82 (3.2H,m)

(232) N- [l- (4-trifluoromethylphenyl) -3- (4- fluorophenylthio) -2-propenylidene] - (5-indanyl) amine (hereinafter, this compound is referred to as "present compound 232".) m.p. :100~103 °C

¹ H-NMR(CDCl ₃ )δ(ppm) : 1.93~2.01 (0.3H,m) , 2.08 —2.15 (1.7H,m) , 2.69—2.82 (0.7H,m) , 2.86—2.93 (3.3H,m) , 6.13 (0.8H,d, J=15.6Hz), 6.29 (0.2H,d,J=8. OHz) , 6.37 (0.2H, d, J=15.6Hz) , 6.44 (0.2H,s) , 6.57 (0.8H,d,J=8. OHz) , 6.67 ( 0.8H, s) , 6.68 (0.2H,d,J=15.6Hz) , 6.80 (0.8H, d, J=15.6Hz) , 6.88—

7 . 52 ( 5H , m) , 7 . 68 ~ 7 . 78 ( 4H, m)

(233) N- Cl- (2-methylphenyl) -3- (4-fluorophenylthio) -2- propenylidene] -4-methylaniline (Hereinafter, this compound is referred to as "present compound 233".)

¹ H-NMR(CDCl ₃ ) δ (ppm) : 2.05 (1.8H, s) , 2.17 (1.8H, s) , 2.35 (1.2H,s) , 2.36 (1.2H,s) , 6.19 (0.4H, d, J=15.5Hz) , 6.40 (0.6H,d, J=15.5Hz) , 6.49~6.53 (2.2H,m) , 6.57 (0.4H,d,J=15.5Hz) , 6.67(0.2H,d, J=8.0Hz), 6.72 (0.8H,d,J=8. OHz) , 6.85(1.4H,d, J=8.2Hz), 6.93~ 7.45 (8H,m)

(234) N- [l- (2-methylphenyl) -3- (4-methylphenylthio) -2- propenylidene] -4-methylaniline (Hereinafter, this compound is referred to as "present compound 234" . )

¹ H-NMR(CDCl ₃ ) δ (ppm) :2.06(1.8H,s), 2.16(1.8H,s), 2.30 (1.2H,s) , 2.35 (3H,s) ,2.36 (1.2H,s) , 6.28(0.4H,d, J=15.5Hz), 6.43 (0.6H, d, J=15.5Hz) , 6.52 (IH, d, J=8.2Hz) , 6.55 (0.6H,d, J=15.5Hz) ,6.63 (0.4H, d, J=15.5Hz) , 6.75 (0.8H, d, J=8 .2Hz) , 6.84(1.2H,d, J=8.2Hz) , 7.03 ~7.34 (9H,m)

(235) N- Cl- (2 -chlorophenyl) -3- (4-fluorophenylthio) -2- propenylidene] -4-methylaniline (Hereinafter, this compound is referred to as "present compound 235".)

¹ H-NMR(CDCl ₃ )δ(ppm) : 2.17 (1.8H, s) , 2.35 (1.2H, s) ,

6.19 (0.4H,d,J=15.4Hz) , 6.40 ( 0.6H, d, J=15.4Hz) , 6.51—

6.59 (2H,m) , 6.76 (0.8H, d, J=8.2Hz) , 6.87 (1.2H ₇ d, J=8. OHz) ,6.95

~7.47(9H,m)

(236) N- [l- (2-chlorophenyl) -3- (4-methylphenylthio) -2- propenylidene] -4-methylaniline (Hereinafter, this compound is referred to as "present compound 236".)

¹ H-NMR(CDCl ₃ )δ (ppm) : 2.16 (1.8H, s) , 2.30 (1.2H, s) , 2.35 (3H,s) , 6.28 (0.4H,d,J=15.6Hz) , 6.43 (0.6H, d, J=15.6Hz) , 6.55~

6.59 (2.6H,m) , 6.62 (0.4H, d, J=15.6Hz) ,6.78 (0.8H, d, J=8. OHz) , 6.86 (1.2H,d, J=7.8Hz) , 6.98—7.43 (8H,m)

(237) N- [l- (2,4-dichlorophenyl) -3- (4 -fluorophenylthio) -2- propenylidene] -4-methylaniline (Hereinafter, this compound is referred to as "present compound 237" . ) 1H-NMR(CDCl ₃ ) δ (ppm) :2.19(1.8H,s), 2.34(1.2H,s),

6.17 (0.4H,d, J=15.6Hz) , 6.37 (0.6H, d, J=15.6Hz) , 6.51~

6.57 (2H,m) , 6.68 (0.2H, d, J=8. OHz) ,6.73 (0.8H, d, J=8. OHz) ,6.88

—7.47 (9H,m)

(238) N- Cl- (2,4-dichlorophenyl) -3- (4-methylphenylthio) -2- propenylidene] -4-methylaniline (Hereinafter, this compound is referred to as "present compound 238".) 1H-NMR(CDCl ₃ )O(PPm) : 2.19 (1.8H, s) , 2.31 (1.2H, s) ,

2.34 (1.2H,s) , 2.35 (1.8H,s) , 6.26 (0.4H, d, J=15.5Hz) ,

6.40 (0.6H,d, J=15.5Hz) , 6.53~6.58(1.6H,m) ,

6.61 (0.4H,d,J=15.5Hz) , 6.68(0.2H,d, J=8.2Hz),

6.76 (0.8H,d,J=8.5Hz) , 6.89 (1.2H, d, J=8. OHz) , 6.93(0.8H,d,

J=8.2Hz), 7.08~7.45(7H,m)

(239) N- Cl- (3-chlorophenyl) -3- (4 -fluorophenyl thio) -2- propenylidene] -4-methylaniline (Hereinafter, this compound

is referred to as "present compound 239".)

¹ H-NMR(CDCl ₃ )δ(ppm) : 2.19 (0.4H, s) , 2.35 (2.6H, s) , 6.05 (0.8H,d, J=15.6Hz) ,6.34 (0.2H, d, J=15.6Hz) ,6.47 (0.8H, d, J=8.2Hz) , 6.69 (0 .2H,d, J=8.2Hz) ,6.73 (0.8H, d, J=15.5Hz) ,6.83 (0.2H, d, J=15.5Hz) , 6.87 — 7.65 (llH,m)

(240) N- [l- (3-chlorophenyl) -3- (4-methylphenylthio) -2- propenylidene] -4-methylaniline (Hereinafter, this compound is referred to as "present compound 240" .)

¹ H-NMR(CDCl ₃ ) δ (ppm) :2.18(0.5H,s),2.31(2.5H,s),2.35(3H,s), 6.15 (0.8H,d, J=15.6Hz) , 6.37 (0.2H, d, J=15.6Hz) ,6.47 (0.4H,d, J=8

.2Hz) ,6.72 (1.6H,d, J=8.2Hz) ,6.76 (0.2H, d, J=15.5Hz) ,6.88 (0.8H, d, J=15.5Hz) ,7.07—7.65 (1OH, m)

(241) N- [l- (2,4-dimethylphenyl) -3- (4-fluorophenylthio) -2- propenylidene] -4-methylaniline (Hereinafter, this compound is referred to as "present compound 241" . ) 1H-NMR(CDCl ₃ ) δ(ppm) : 2.00 (2H, s) , 2.17 (2H, s) , 2.24 (2H, s) ,

2.31 ( IH, s), 2.32 (IH, s), 2.34 (IH, s), 6.18 (0.4H, d, J=15.4Hz) ,6.39 (0.6H,d, J=15.4Hz) ,6.50 — 6.54 (1.9H,m) ,6.59 (0.4H, d, J=15.4Hz) , 6.71 (0.7H,d,J=8. OHz) , 6.84 —7.44 (9H, m)

(242) N- [l- (2,4-dimethylphenyl) -3- (4-methylphenylthio) -2- propenylidene) -4-methylaniline (Hereinafter, this compound is referred to as "present compound 242" . ) 1H-NMR(CDCl ₃ ) δ(ppm) : 2.01 (2H, s) , 2.16 (2H, s) , 2.23 (2H, s) , 2.29 ( IH, s) ,2.31(2H,s) ,2.34 (3H,s) ,6.27 (0.4H, d, J=15.4Hz) ,6.42 (0.6H,d, J=15.4Hz) , 6.51-6.58 (1.9H,m) , 6.64 (0.4H, d, J=15.4Hz) ,

6.74 (0.7H,d, J=8.0Hz) , 6.84 ~ 7.33 (9H,m)

(243) N- [l- (2 -fluorophenyl) -3- (4-fluorophenylthio) -2- propenylidene] -4-methylaniline (Hereinafter, this compound is referred to as "present compound 243" . ) 1H-NMR(CDCl ₃ ) δ(ppm) : 2.17 (1.7H, s) , 2.34 (1.3H, s) , 6.18(0.4H,d, J=15.6Hz), 6.40 (0.6H, d, J=15.6Hz) ,

6.53 (1.2H,d,J=8. OHz) , 6.66 (0.6H, d, J=15.4Hz) , 6.69— 6.74(2H,m), 6.87 (1.2H, d, J=8. OHz) , 6.93~7.49 (8H,m)

(244) N- [l- (2 -fluorophenyl) -3- (4-methylphenylthio) -2- propenylidene] -4-methylaniline (Hereinafter, this compound is referred to as "present compound 244".) 1H-NMR(CDCl ₃ ) δ(ppm) : 2.16 (1.8H, s) , 2.30 (1.2H, s) ,

2.34 (1.8H ₇ S) , 2.35(1.2H,s) ,6.27 (0.4H, d, J=15.6Hz) ,

6.43 (0.6H,d, J=15.1Hz) ,6.52 (IH, d, J=8. OHz) ,6.69 (0.6H, d, J=15.4

Hz) ,6.74—6.79 (1.4H,m) , 6.86 (IH, d, J=8. OHz) , 6.93 ~7.49 (9H,m)

(245) N- [l- (4 -fluorophenyl) -3- (4-f luorophenylthio) -2- propenylidene) -4-methylaniline (Hereinafter, this compound is referred to as "present compound 245" .) m.p. :108 — 111 °C

¹ H-NMR(CDCl ₃ ) δ(ppm) : 2.19 (0.6H, s) , 2.35 (2.4H, s) , 6.06 (0.8H,d,J=15.6Hz) , 6.37(0.2H, d, J=15.6Hz), 6.46(0.4H,d, J=8.2Hz) , 6.69 (1.6H, d, J=8. OHz) ,

6.75(0.2H,d, J=15.4Hz) , 6.81(0.8H,d, J=15.6Hz) , 6.87~ 7.67 (1OH, m)

(246) N- Cl- (4-fluorophenyl) -3- (4-methylphenylthio) -2-

propenylidene) -4-methylaniline (Hereinafter, this compound is referred to as "present compound 246" . ) m.p. :77~82 °C

¹ H-NMR(CDCl ₃ ) δ (ppm) :2.19(0.6H,s) ,2.31(2.4H,s) ,2.35(3H,s), 6.16 (0.8H,d,J=15.6Hz) ,6.40 (0.2H, d, J=15.4Hz) , 6.46 (0.4H, d, J=8 .2Hz) ,6.72 (1.6H,d, J=8.0Hz) ,6.78 (0.2H, d, J= 15.4Hz) , β.84~ 6.94 (1.8H,m) , 7.07~7.66 ( 9H,m)

(247) N- [l- (2,4-difluorophenyl) -3- (4-f luorophenylthio) -2- propenylidene] -4-methylaniline (Hereinafter, this compound is referred to as "present compound 247".) 1H-NMR(CDCl ₃ ) δ (ppm) :2.19 (1.5H,s) , 2.34 (1.5H, s) ,

6.15 (0.5H,d, J=15.6Hz) ,6.39 (0.5H, d, J=15.4Hz) , 6.50 (IH, d, J=8.3Hz) , 6.64 — 7.50 (llH,m)

(248) N- [l- (2, 4-difluorophenyl) -3- (4-methylphenylthio) -2- propenylidene] -4-methylaniline (Hereinafter, this compound is referred to as "present compound 248".) m.p. :88~92 °C

¹ H-NMR(CDCl ₃ ) δ (ppm) : 2.18 (1.5H,s) , 2.31 (1.5H, s) ,

2.34(1.5H,s), 2.35(1.5H,s),6.25 (0.5H, d, J=15.6Hz) ,

6.41 (0.5H,d, J=15.4Hz) ,6.50 (IH, d, J=8. OHz) , 6.67—7.51 (HH,m)

(249) N- Cl- (4-isopropylphenyl) -3- (4-fluorophenylthio) -2- propenylidene] -4-methylaniline (Hereinafter, this compound is referred to as "present compound 249".) m.p. :148~150 °C

¹ H-NMR(CDCl ₃ ) δ(ppm) :1.19 (IH, d, J=7. OHz) ,1.25 (5H, d, J=7. OHz) ,

2.19(0.5H,s) ,2.35(2.5H,s) ,2.78— 2.99(lH,m) ,6.08(0.8H,d, J=15.6Hz) , 6.37 ( 0.2H, d, J= 15.4Hz) ,6.49 (0.3H, d, J=8.2Hz) , 6.70(1.7H,d, J=8.2Hz) , 6.80 (0.2H, d, J=15.6Hz) , 6.87 (0.8H, d, J=15.6Hz) , 6.93— 7.59 (10H,m)

(250) N- Cl- (4-isopropylphenyl) -3- (4-methylphenylthio) -2- propenylidene] -4-methylaniline (Hereinafter, this compound is referred to as "present compound 250" . ) m.p. :107~110 °C

¹ H-NMR(CDCl ₃ ) δ(ppm) :1.19 (IH, d, J=7. IHz) ,1.26 (5H, d, J=7. IHz) ,

2.19 (0.5H,s) ,2.31(2.5H,s) ,2.35 (3H,s) ,2.79 — 2.99 (IH, m) ,

6.17 (0.8H,d, J=15.6Hz) ,6.40 (0.2H, d, J=15.4Hz) , 6.49 ( 0.2H, d, J=8

.2Hz) ,6.73 (1.6H,d, J=8.2Hz) ,6.83 (0.2H, d, J=15.4Hz) ,6.93 (0.8H, d, J=15.4Hz) ,6.97 (0.2H, d, J=8. OHz) ,7.07 — 7.59 (1OH, m)

(251) N- [l- (3,4-dichlorophenyl) -3- (4-f luorophenylthio) -2- propenylidene] -4-methylaniline (Hereinafter, this compound is referred to as "present compound 251" . ) m.p. :110~114 °C

¹ H-NMR(CDCl ₃ )δ (ppm) :2.21(0.6H,s) ,2.35(2.4H,s) ,6.04(0.8H, d, J=15.6Hz) ,6.32 (0.2H, d, J=15.5Hz) ,6.46 (0.3H, d, J=8.4Hz) ,6.68 (1.7H,d, J=8.2Hz) , 6.75 ( 0.2H, d, J=15.5Hz) ,6.82 (0.8H, d, J= 15.6Hz ) ,6.89 — 7.76(9H,m)

(252) N- [l- (3,4-difluorophenyl-3- (4- fluorophenylthio) propenylidene) -4-methylaniline (Hereinafter, this compound is referred to as "present compound 252" . )

m.p. :78~80 °C

¹ H-NMR(CDCl ₃ ) δ (ppm) :2.21(0.5H,s) ,2.36(2.5H,s) , 6.02(0.8H,d,

J=15.6Hz) , 6.33 (0.2H, d, J=15.4Hz) ,6.45 (0.3H, d, J=8.4Hz) ,

6.68 (1.7H,d, J= 8.4Hz) ,6.76 ( 0.2H, d, J=15.5Hz) , 6.83 (0.8H, d, J=15

.5Hz) , 6.89 — 7.54 (9H,m)

(253) N- Cl- (2,3-dichlorophenyl) -3- (4 - fluorophenylthio) -2- propenylidene] -4-methylaniline (Hereinafter, this compound is referred to as "present compound 253".)

¹ H-NMR(CDCl ₃ ) δ (ppm) :2.18(1.7H,s),2.35(1.3H,s),6.17(0.4H,d, J=15.5Hz) ,6.35 (0.6H, d, J=15.5Hz) , 6.51~6.57 (2.2H,m) , 6.75(0.8H,d, J=8.2Hz), 6.87~7.51 (9H,m)

(254) N- [l- (3,5-dichlorophenyl) -3- (4-fluorophenylthio) -2- propenylidene] -4-methylaniline (Hereinafter, this compound is referred to as "present compound 254" . )

¹ H-NMR(CDCl ₃ ) δ (ppm) :2.20(0.4H,s),2.35(2.6H,s),6.01(0.8H,d, J=15.6Hz) ,6.29 (0.2H, d, J=15.6Hz) ,6.46 (0.3H, d, J=8.3Hz) ,6.67 (1 .7H,d, J=8.0Hz) ,6.74 ( 0.2H, d, J=15.6Hz) ,6.83 (0.8H, d, J=15.4Hz) , 6.90 —7.53 (9H,m)

(255) N- Cl- (3, 5-difluorophenyl) -3- (4-fluorophenylthio) -2- propenylidene] -4-methylaniline (Hereinafter, this compound is referred to as "present compound 255" . ) m.p. :88~92 °C

¹ H-NMR(CDCl ₃ ) δ(ppm) :2.20(0.4H,s) ,2.35(2.6H,s) ,6.01(0.8H,d, J=15.6Hz) ,6.31(0.2H,d, J=15.4Hz) , 6.47 (0.3H, d, J=8.3Hz) ,6.67(1 .7H,d, J=8.0Hz) ,6.76 (0.2H, d, J=15.6Hz) ,6.85 (0.8H, d, J=15.6Hz) ,

6.88~7.49(9H,m)

(256) N- [l- (3,5-dimethylphenyl) -3- (4 -fluorophenylthio) -2- propenylidene] -4-methylaniline (Hereinafter, this compound is referred to as "present compound 256" . )

¹ H-NMR(CDCl ₃ ) δ(ppm) : 2.20 (1. IH, s) , 2.35 (7.9H, s) , 6.08 (0.8H,d, J=15.6Hz) ,6.35 (0.2H, d, J=15.2Hz) ,6.50 (0.3H,d, J=8 .0Hz) ,6.69 (1.7H,d, J=8.0Hz) ,6.75 (0.2H, d, J=15.4Hz) , 6.85 (0.8H, d, J=15.6Hz) , 6.93 —7.31 (9H,m)

(257) N- [l- (3,4-dimethylphenyl) -3- (4 -fluorophenylthio) -2- propenylidene] -4-methylaniline (Hereinafter, this compound is referred to as "present compound 257" . ) m.p. :101~104 ⁰ C

¹ H-NMR(CDCl ₃ ) δ (ppm) :2.16(0.5H,s),2.19(lH,s),2.30(5H,s), 2.35(2.5H,s),6.09 (0.8H, d, J=15.6Hz) ,6.37 (0.2H, d, J=15.4Hz) , 6.50 (0.3H,d,J=8.3Hz) , 6.70 (1.7H, d, J=8. OHz) , 6.77(0.2H,d, J=15.4Hz), 6.86 ( 0.8H, d, J=15.6Hz) , 6.94~7.45 (9H,m)

(258) N- [l- (4-methylphenyl) -3- (4-fluorophenylthio) -2- propenylidene) -4-methylaniline (Hereinafter, this compound is referred to as "present compound 258" . ) m.p. :101~105 ⁰ C

¹ H-NMR(CDCl ₃ ) δ (ppm) :2.19(0.7H,s) ,2.28(0.7H,s) ,

2.35(2.3H,S) , 2.39 (2.3H,s) , 6.09 (0.8H, d, J=15.6Hz) ,

6.38 (0.2H,d, J=15.4Hz) ,6.49 (0.4H, d, J=8.3Hz) , 6.70 (1.6H, d, J=8.

3Hz) ,6.77(0.2H,d, J=15.4Hz) ,6.84 (0.8H, d, J=15.6Hz) ,6.93~ 7.55 (1OH, m)

(259) N- [l- (4-chlorophenyl) -3- (4-fluorophenylthio) -2- propenylidene] -4-methylaniline (Hereinafter, this compound is referred to as "present compound 259" . ) m.p. :116~119 °C

¹ H-NMR(CDCl ₃ ) δ (ppm) :2.20(0.6H,s) ,2.35(2.4H,s) ,6.06(0.8H,d, J=15.6Hz) ,6.37 (0.2H, d, J=15.4Hz) ,6.46 ( 0.4H, d, J=8. OHz) ,6.69 (1 .6H,d, J=8.3Hz) ,6.74 (0.2H, d, J=15.4Hz) ,6.81 (0.8H, d, J=15.6Hz) , 6.87—7.60 (1OH, m)

(260) N- [l- (3-trifluoromethylphenyl) -3- (4- fluorophenylthio) -2-propenylidene] -4-methylaniline

(Hereinafter, this compound is referred to as "present compound 260" . ) m.p. :66~69 ⁰ C

¹ H-NMR(CDCl ₃ ) δ (ppm) :2.18 (0.4H,s) , 2.36 (2.6H, s) ,

6.11(0.8H,d, J=15.6Hz), 6.39 (0.2H, d, J=15.4Hz) ,

6.44 (0.4H,d, J=8.4Hz) , 6.71 (1.6H, d, J=8.2Hz) ,

6.72 (0.2H,d, J=15.2Hz) , 6.81 (0.8H, d, J=15.6Hz) ,6.86~ 7.92 (1OH, m)

(261) N- Cl- (2, 6 -difluorophenyl -3- (4- fluorophenylthio) propenylidene) -4-methylaniline

(Hereinafter, this compound is referred to as "present compound 261" .) m.p. :77~79 ⁰ C

¹ H-NMR(CDCl ₃ )δ(ppm) : 2.18 (2.6H, s) , 2.23 (0.4H, s) , 6.20 (0.2H,d,

J=15.2Hz) , 6.41(0.8H,d, J=15.5Hz) ,6.57 (1.7H, d, J=8.2Hz) ,6.64

~ 6 . 81 ( 4H , m) , 6 . 89 ( 1 . 7H , d , J= 8 . 2Hz ) , 6 . 95 ~ 7 . 54 ( 4 . 6H , m)

(262) N- [1- (4-trifluormethylphenyl) -3- (4-fluorophenylthio) - 2-propenylidene] -2-chloroaniline (Hereinafter, this compound is referred to as "present compound 262" . ) 1H-NMR(CDCl ₃ ) δ (ppm) : 5.81 (IH, d, J=15.9Hz) , 6.38-7.53 (9H,m) , 7.68-7.84 (4H,m)

(263) N- [1- (4-trifluormethylphenyl) -3- (4-fluorophenylthio) - 2-propenylidene] -2-fluoroaniline (Hereinafter, this compound is referred to as "present compound 263".) 1H-NMR(CDCl ₃ ) δ (ppm) : 5.93 (IH, d, J=15.4Hz) , 6.35-7.54 (9H, m) , 7.67-7.81 (4H,m)

(264) N- [1- (2-trifluormethylphenyl) -3- (4-fluorophenylthio) - 2-propenylidene] -4-methylaniline (Hereinafter, this compound is referred to as "present compound 264" .) 1H-NMR(CDCl ₃ ) δ (ppm) : 2.15 (0.3H,s) , 2.34 (0.7H, s) , 6.22(0.7H,d, J=15.9Hz), 6.42-7.77 (12.3H,m)

(265) N- [1- (4-trifluoromethoxyphenyl) -3- (4- fluorophenylthio) -2-propenylidene] -4-methylaniline

(Hereinafter, this compound is referred to as "present compound 265" . ) m.p. :78~83 °C

¹ H-NMR(CDCl ₃ ) δ (ppm) : 2.19 ( 0.2H, s) , 2.36 (0.8H, s) ,

6.06(0.8H,d, J=15.6Hz), 6.32-7.75 (10.2H,m) , 7.65-7.71 (2H,m)

(266) N- [1- (4-cyanopheny1) -3- (4-fluorophenylthio) -2- propenylidene] -4-methylaniline (Hereinafter, this compound

is referred to as "present compound 266".) m.p. :160~164 °C

¹ H-NMR(CDCl ₃ ) δ(ppm) : 2.34 (3H,s), 6.18 (0.5H, d, J=15. IHz) ,

6.40(0.5H,d, J=15.1Hz), 6.50-7.55 (13H, m)

(267) N- [1- (4-bromophenyl) -3- (4 - fluorophenylthio) -2- propenylidene] -4-methylaniline (Hereinafter, this compound is referred to as "present compound 267" . ) m.p. :130~133 °C

(268) N-[I- (3-bromophenyl) -3- (4-fluorophenylthio) -2- propenylidene] -4-methylaniline (Hereinafter, this compound is referred to as "present compound 268" . ) 1H-NMR(CDCl ₃ ) δ (ppm) : 2.18 (0.2H, s) , 2.35 (0.8H, s) , 6.06(0.8H,d, J=15.3Hz), 6.33 (0.2H, d, J=15.3Hz) , 6.43- 7.84 (l2H,m)

(269) N- [1- (2-bromophenyl) -3- (4-fluorophenylthio) -2- propenylidene] -4-methylaniline (Hereinafter, this compound is referred to as "present compound 269" . ) 1H-NMR(CDCl ₃ ) δ(ppm) 2.19(0.5H, s) , 2.35 (0.5H, s) , 6.05(0.5H, d, J=15.5Hz), 6.35(0.5H, d, J=15.5Hz), 6.50- 7.8O(12H, m)

(270) N- [1- (2-methylphenyl) -3- (4-fluorophenylthio) -2- propenylidene] -3-methylaniline (Hereinafter, this compound is referred to as "present compound 270".) 1H-NMR(CDCl ₃ ) δ(ppm) : 2.07 (0.5H, s) , 2.15 (0.5H, s) , 2.33(0.5H,s), 2.37(0.5H,s) , 6.17 (0.5H, d, J=15.3Hz) ,6.34-

7 . 70 ( 3 . 5H , m) , 6 . 85 - 7 . 48 ( 10H, m)

(271) N-[I- (2-methylphenyl) -3- (4-fluorophenylthio) -2- propenylidene] -2-methylaniline (Hereinafter, this compound is referred to as "present compound 271" . ) 1H-NMR(CDCl ₃ ) δ(ppm): 2.09-2.17 (3H,m) , 2.23 (IH, s),

2.38 (2H,s) , 6.02 (0.7H, d, J=15.6Hz) ,6.25 (0.3H, d, J^=15.6Hz) , 6.45-7.46 (13H,m)

(272) N- [1- (2 -fluorophenyl) -3- (4-fluorophenylthio) -2- propenylidene] -3-methylaniline (Hereinafter, this compound is referred to as "present compound 272".) 1H-NMR(CDCl ₃ ) δ (ppm) : 2.16 (1.5H, s) , 2.33 (1.5H, s) , 6.17(0.5H, d, J=15.4Hz) ,6.37-6.49 (1.5H,m) , 6.50-

6.66 (2.5H,m) , 6.45-7.51 (9.5H,m)

(273) N- [1- (2 -fluorophenyl) -3- (4-fluorophenylthio) -2- propenylidene] -2-methylaniline (Hereinafter, this compound is referred to as "present compound 273".) 1H-NMR(CDCl ₃ ) δ (ppm) : 2.10 (1.5H, s) , 2.15 (1.5H, s) , 6.00(0.5H,d, J=15.2Hz), 6.48 (0.5H, d, J=15.2Hz) , 6.64- 7.30 (llH,m) , 7.35-7.52 (2H,m)

(274) N-[I- (2 -fluorophenyl) -3- (4-fluorophenylthio) -2- propenylidene] -4-fluoroaniline (Hereinafter, this compound is referred to as "present compound 274" . ) 1H-NMR(CDCl ₃ ) δ(ppm) : 6.12 (0.5H, d, J=15.2Hz) ,6.37 (0.5H,d, J=15.2Hz) , 6.54-6.82 (4.5H,m) ,6.90-7.50 (8.5H,m)

(275) N- [1- (2 -fluorophenyl) -3- (4-fluorophenylthio) -2-

propenylidene] -aniline (Hereinafter, this compound is referred to as "present compound 275" . ) m.p. :81~83 ⁰ C

¹ H-NMR(CDCl ₃ ) δ (ppm) : 6.15 (0.5H,d,J=15.3Hz) , 6.40(0.5H,d,

J=15.3Hz), 6.60-7.52 (14H,m)

(276) N- [1- (3 -fluorophenyl) -3- (4-fluorophenylthio) -2- propenylidene] -4-fluoroaniline (Hereinafter, this compound is referred to as "present compound 276" . )

¹ H-NMR(CDCl ₃ ) δ(ppm) : 2.19 (0.6H, s) , 2.36 (2.4H,s) ,6.08 (0.8H ₇ (I ₇ J=15.4Hz) ,6.30-7.18(9.2H,m),7.28-7.50(4H,m)

(277) N- [1- (4-fluorophenyl) -3- (4-fluorophenylthio) -2- propenylidene] -3-methylaniline (Hereinafter, this compound is referred to as "present compound 277" . ) 1H-NMR(CDCl ₃ ) δ(ppm) : 2.18 (0.6H, s) , 2.26 (0.6H,s) , 2.35(2.4H,s), 2.26(2.4H,s),6.08 (0.8H, d, J=15.6Hz) ,6.33- 7.50 (13.2H,m)

(278) N- [1- (2,3-dimethylphenyl) -3- (4-fluorophenylthio) -2- propenylidene] -4-methylaniline (Hereinafter, this compound is referred to as "present compound 278" . ) 1H-NMR(CDCl ₃ ) δ(ppm) :1.96 (1.8H,s) , 2.27 (3.9H, s) ,

2.23 (1. IH, s) , 2.30 (1. IH, s) ,2.35 (1. IH, s) ,6.17-7.18 (12H,mK 7.41-7.48 (IH, m)

(279 ) N- [1- (2 - fluorophenyl) -3 - (4- f luorophenylthio) -2 - propenylidene] -3 -chloroaniline (Hereinafter, this compound is referred to as "present compound 279" . )

m.p. :89~91 °C

¹ H-NMR(CDCl ₃ ) δ (ppm) :5.98 (0.5H,d, J=15.2Hz) , 6.45(0.5H,d,

J=15.2Hz) , 6.45-7.45(1OH, m) , 7.47-7.55 (3H,m)

(280) N- [1- (2-fluorophenyl) -3- (4 -fluorophenylthio) -2- propenylidene] -4-chloroaniline (Hereinafter, this compound is referred to as "present compound 280".) 1H-NMR(CDCl ₃ ) δ (ppm) : 6.09 (0.5H, d, J=15.2Hz) , 6.35(0.5H,d, J=15.2Hz) , 6.55 (IH, d, J=8.4Hz) ,6.68-7.50 (12H,m)

(281) N- [1- (2-fluorophenyl) -3- (4 -fluorophenylthio) -2- propenylidene] -3-bromoaniline (Hereinafter, this compound is referred to as "present compound 281".) m.p. :84~87 °C

¹ H-NMR(CDCl ₃ ) δ(ppm) : 5.97 (0.5H, d, J=15.2Hz) , 6.35(0.5H,d, J=15.2Hz), 6.45-6.60 (IH, m) ,6.70-6.83 (2.5H,m) , 6.90- 7.50 (9.5H,m)

(282) N- [1- (2-fluorophenyl) -3- (4-fluorophenylthio) -2- propenylidene] -4-bromoaniline (Hereinafter, this compound is referred to as "present compound 282".) m.p. :92~96 ⁰ C

¹ H-NMR(CDCl ₃ ) δ (ppm) :6.08 (0.5H,d, J=15.4Hz) , 6.35(0.5H,d, J=15.4Hz), 6.50 (IH, d, J=8.4Hz) , 6.67-6.81 (1.5H,m) , 6.91- 7.50 (9.5H,m)

(283) N- [1- (2-fluorophenyl) -3- (4-fluorophenylthio) -2- propenylidene] -2-fluoroaniline (Hereinafter, this compound is referred to as "present compound 283".)

m.p. :76^-78 °C

¹ H-NMR(CDCl ₃ ) δ (ppm) : 6.00 (0.5H, d, J=15.3Hz) , β.42(0.5H,d,

J=15.3Hz) , 6.61-7.35 ( HH, m) , 7.38-7.55 (2H,m)

(284) N- [1- (2 -fluorophenyl) -3- (4 -fluorophenylthio) -2- propenylidene] -3-fluoroaniline (Hereinafter, this compound is referred to as "present compound 284" . ) m.p. :82~85 °C

¹ H-NMR(CDCl ₃ ) δ (ppm) :6.02 (0.5H, d, J=15.3Hz) ,

6.30 (0.5H,d, J=15.3Hz) , 6.48-6.83 (3H,m) , 6.90-7.52 ( 8.5H,m)

(285) N- [1- (2 -fluorophenyl) -3- (4-fluorophenylthio) -2- propenylidene] -3 , 4-dimethylaniline (Hereinafter, this compound is referred to as "present compound 285".) 1H-NMR(CDCl ₃ ) δ (ppm) :2.02-2.27(6H,m),6.19 (0.5H, d, J=15.4Hz) , 6.30-6.49 (1.5H,m) , 6.44-6.82 (2.5H,m) ,6.90-7.52 (8.5H,m)

(286) N- [1- (4-methoxyphenyl) -3- (4-fluorophenylthio) -2- propenylidene] -4-methylaniline (Hereinafter, this compound is referred to as "present compound 286".) m.p. :97—100 °C

¹ H-NMR(CDCl ₃ ) δ (ppm) :2.20 (0.6H,s) , 2.35 (2.4H, S) ,

3.75(0.6H,s) , 3.84 (2.4H,s) , 6.07 (0.8H, d, J=15.5Hz) ,

6.48 (0.2H,d, J=15.5Hz) ,6.65-7.13(9H,m),7.23-

7.32 (2H,m) ,7.62 (2H, d, J=8.7Hz)

(287) N- [1- (2,5-dichlorophenyl) -3- (4-fluorophenylthio) -2- propenylidene] -4-methylaniline (Hereinafter, this compound is referred to as "present compound 287".)

m.p. :124~127 °C

¹ H-NMR(CDCl ₃ ) δ(pptn) :2.19(1.5H,s) , 2.35 (1.5H, S) ,

6.15(0.5H,d, J=15.3Hz) , 6.33 (0.5H, d, J=15.3Hz) ,6.50-

6.61(2H,m),6.70-7.78(lH,m),6.85-7.50(9H,m)

(288) N- [1- (2-chloro-6-fluoromethylphenyl) -3- (4- fluorophenylthio) -2-propenylidene] -4 -methylaniline

(Hereinafter, this compound is referred to as "present compound 288" .) m.p. :97~100 °C

¹ H-NMR(CDCl ₃ ) δ (ppm) : 2.19 (1.5H, s) , 2.35 (1.5H, S) , 6.15 (0.5H, d,

J=15.3Hz) , 6.33 (0.5H, d, J=15.3Hz) ,6.50-6.61(2H ₁ Tn), 6.70-

7.78 (lH,m) ,6.85-7.50 (9H,m)

(289) N- [1- (2,6-dimethylphenyl) -3- (4-fluorophenylthio) -2- propenylidene] -4-methylaniline (Hereinafter, this compound is referred to as "present compound 289".) 1H-NMR(CDCl ₃ ) δ(ppm) : 2.10-2.37 (9H,m) , 6.22(0.3H,d, J=15.2Hz) ,6.37-6.58(3H,m),6.70-7.00(4H,m),7.03-

7.30 (4.2H,m) , 7.39-7.36 (1.5H,m)

(290) N- [1- (2-fluoro-4-trifluormethylphenyl) -3- (4- fluorophenylthio) -2-propenylidene] -4-methylaniline (Hereinafter, this compound is referred to as "present compound 290" .) m.p. :1027~105 ⁰ C

¹ H-NMR(CDCl ₃ ) δ(ppm): 2.19 (1.5H, s) , 2.35 (1.5H, s) ,

6.17(0.5H, d, J=15.6Hz), 6.37 (0.5H, d, J=15.6Hz) ,

6.49 (0.5H,d, J=8.2Hz) , 6.59-6.75 (2H,m) , 6.88 (0.5H,d, J=8.2Hz) , 6.86-7.55 (8H,m) ,

(291) N- [1- (1-naphthyl) -3- (4-fluorophenylthio) -2- propenylidene] -4-methylaniline (Hereinafter, this compound is referred to as "present compound 291" . ) m.p. :102~105 °C

¹ H-NMR(CDCl ₃ ) δ(ppm) :2.05(2H,s) , 2.37 (IH, s) , 6.33-

7.21(10H,m), 7.31-7.57 (4H,m) , 7.70-8.07 (3H,m)

(292) N- [1- (2-naphthyl) -3- (4-fluorophenylthio) -2- propenylidene] -4-methylaniline (Hereinafter, this compound is referred to as "present compound 292" . ) m.p. :117~120 °C

¹ H-NMR(CDCl ₃ ) δ(ppm): 2.12 (IH, s), 2.37(2H,s),

6.18 (0.7H,d,J=15.6Hz) , 6.47(0.3H,d, J=15.6Hz) , 6.70-

7.16 (7H,m) ,7.26-8.17 (9H,m)

(293) N- [1- (2, 5-difluorophenyl) -3- (4-fluorophenylthio) -2- propenylidene] -4-methylaniline (Hereinafter, this compound is referred to as "present compound 293".) m.p. :79~82 ⁰ C

¹ H-NMR(CDCl ₃ ) δ(ppm) : 2.19 (1.5H, s) , 2.34 (1.5H,s) ,6.14 (0.5H,d, J=15.6Hz) , 6.35 (0.5H, d, J=15.6Hz) ,6.52 (IH, d, J=8.2Hz) ,6.63- 6.77 (2.5H,m) ,6.85-7.35 (7.5H,m) ,7.43-7.52 (IH, m)

(294) N- [1- (2 , 5-difluorophenyl) -3- (4-fluorophenylthio) -2- propenylidene] -aniline (Hereinafter, this compound is referred to as "present compound 294".)

¹ H-NMR(CDCl ₃ ) δ (ppm) : 6.04 (0.8H, d, J= 15.5Hz) , 6.36(0.2H,d, J=15.5Hz) , 6.52-6.63 (2H,m) , 6.72-7.55 (10H,m) , 7.58- 7.65 (2H,m)

(295) N- [1- (2, 5-difluorophenyl) -3- (4-methylphenylthio) -2- propenylidene] -aniline (Hereinafter, this compound is referred to as "present compound 295".)

¹ H-NMR(CDCl ₃ ) δ (ppm) : 2.27-2.34 (3H,m) , 6.10(0.5H,d, J=15.6Hz), 6.75-7.45 (12.5H,m) , 7.53 -7.63 (2H,m)

(296) N- [1- (4-chlorophenyl) -3- (4-f luorophenylthio) -2- propenylidene] -3-methylaniline (Hereinafter, this compound is referred to as "present compound 296".)

¹ H-NMR(CDCl ₃ ) δ(ppm) :2.18 (IH, s) , 2.33 (2H,s), 6.05(0.5H,d, J=15.6Hz), 6.52-6.62 (2H,m) , 6.82 (0.5H, d, J=15.6Hz) , 6.88- 7.52(9H,m) , 7.56-7.65 (2H,m)

(297) N- [1- (4-chlorophenyl) -3- (4-methylphenylthio) -2- propenylidene] -3-methylaniline (Hereinafter, this compound is referred to as "present compound 297".) 1H-NMR(CDCl ₃ ) δ(ppm) : 2.15-2.38 (6H, s) , 6.11(0.7H,d, J=15.5Hz) , 6.56-6.63(2H,m),6.75-7.43(9.3H,m),7.55-

7.62 (2H,m)

(298) N- [1- (4-chlorophenyl) -3- (4-fluorophenylthio) -2- propenylidene] -2-chloroaniline (Hereinafter, this compound is referred to as "present compound 298".) 1H-NMR(CDCl ₃ ) δ(ppm) :5.80 (0.7H, d, J=15.4Hz) ,6.38-

6.45 (1.3H,m) ,6.70-7.56 (10H,m) , 7.60-7.70 (2H,m)

(299) N- [1- (4-chlorophenyl) -3- (4-methylphenylthio) -2- propenylidene] -3-chloroaniline (Hereinafter, this compound is referred to as "present compound 299" . ) 1H-NMR(CDCl ₃ ) δ (ppm) :2.31 (IH, s) , 2.34(2H,s), 5.88 (0.5H,d,J=15.6Hz) , 6.40-6.48 (0.5H,m) , 6.75- 7.50 (llH,m) ,7.58-7.68(2H,m)

Production Example 307

N- [1- (2-chloro-4-fluorophenyl) -3- (4 -fluorophenylthio) -2- propenylidene] -4-methylaniline (Hereinafter described as the present compound 307)

Into a methanol solution (5 ml) of N- [1- (2-chloro-4- fluorophenyl) -3-trimethylsilyl-2-propylidene] -4- methylaniline (0.28 g) , a methanol solution (2 ml) of 4- fluorothiophenol (0.1 g) was dropped under ice cool and the mixture was stirred for 45 minutes at room temperature. Next, potassium carbonate (0.1 g) was added and stirred at 50°C for 3 hours. The reaction mixture was concentrated under reduced pressure condition and the resultant residue was subjected to silica gel column chromatography (hexane: ethyl acetate = 10:1) to obtain the present compound 307 (0.27 g) .

¹ H-NNR (CDCl ₃ ) δ(ppm): 2.19 (1.5H, s) , 2.35 (1.5H, s) , 6.17 (0.5H, d, J = 15.2 Hz), 6.38 (0.5H, d, J = 15.2 Hz), 6.50-7.32 (8.5H, m) , 7.35-7.49 (1.5H, m)

Production Examples 300 to 302

N- [1- (4-chlorophenyl) -3- (4-fluorophenylthio) -2- propenylidene] -3-chloroaniline (Hereinafter described as the present compounds 300 to 302) (1) Into a methanol solution (15 ml) of N- [1- (4- chlorophenyl) -3-trimethylsilyl-2-propylidene] -3-chloroaniline (1.2 g), a methanol solution (5 ml) of 4- fluorothiophenol (0.44 g) was dropped under ice cool and the mixture was stirred for 22 hours at room temperature. The reaction mixture was concentrated under reduced pressure condition and the resultant residue was subjected to silica gel column chromatography (hexane : ethyl acetate = 10:1) to obtain N- [1- (4-chlorophenyl) -3-trimethylsilyl-3- (4-fluorophenylthio) -2-propenylidene] -3-chloroaniline (1.64 g, compound A) .

(2a) To a methanol solution (15 ml) of the compound A (0.7 g) was added potassium carbonate (0.2 g) and the mixture was stirred at 50°C for 3 hours. The reaction mixture was concentrated under reduced pressure condition and the resultant residue was subjected to silica gel column chromatography (hexane : ethyl acetate = 15:1) to obtain the present compound 300 (0.45 g) .

¹ H-NNR (CDCl ₃ ) δ(ppm): 5.86 (0.5H, d, J = 15.6 Hz), 6.42 (0.5H, d, J = 9.5 Hz), 6.53-7.62 (12H, m) , 7.74-8.00

( IH, m)

(2b) To a methanol solution (15 ml) of the compound A (0.7 g) was added potassium carbonate (0.2 g) and the mixture was stirred at room temperature for 3 days. The reaction mixture was concentrated under reduced pressure condition and the resultant residue was subjected to silica gel column chromatography (hexane : ethyl acetate = 15:1), to isolate and purify a compound of high Rf value (0.11 g, the present compound 301) and a compound of low Rf value (0.27 g, the present compound 302) , respectively. Present compound 301

¹ H-NNR (CDCl ₃ ) δ (ppm) : 5.86 (0.5H, d, J = 15.6 Hz), 6.39-7.36 (7.5H, m) , 7.38-7.60 (6H, m) Present compound 302

¹ H-NNR (CDCl ₃ ) δ(ppm): 5.86 (0.5H, d, J = 15.6 Hz), 6.60-7.35 (7.5H, m) , 7.38-7.62 (5H, m) , 7.73-8.00 (IH, m)

Production Examples 303 to 306, 308 and 309 The following compounds were produced according to the methods of production examples 307 and 300 to 302. (303) N- [1- (4-chlorophenyl) -3- (4-fluorophenylthio) -2- propenylidene] -2-methylaniline (Hereinafter, this compound is referred to as "present compound 303".) 1H-NMR(CDCl ₃ ) δ (ppm) :2.04-2.29(3H,m) , 5.93(0.5H,d, J=15.6Hz) , 6.40-7.27 (9.5H,m) , 7.38-7.65 (4H,m)

(304) N- [1- (4-chlorophenyl) -3- (4 -fluorophenylthio) -2- propenylidene] -4-fluoroaniline (Hereinafter, this compound is referred to as "present compound 304".)

¹ H-NMR(CDCl ₃ ) δ (ppm) : 5.98-6.43 (lH,m) , 6.48-7.35 (10H,m) ,7.38- 7.85(3H,m)

(305) N- [1- (4-chlorophenyl) -3- (4-fluorophenylthio) -2- propenylidene] -3-fluoroaniline (Hereinafter, this compound is referred to as "present compound 305".) 1H-NMR(CDCl ₃ ) δ (ppm) :5.91(0.8H,d,J=15. IHz) , 6.27- 6.68(2.4H,m) , 6.73-7.56(9.8H,m) ,7.56-7.62 (2H,m)

(306) N- [1- (4-chlorophenyl) -3- (4-fluorophenylthio) -2- propenylidene] -2-fluoroaniline (Hereinafter, this compound is referred to as "present compound 306".) 1H-NMR(CDCl ₃ ) δ (ppm) : 5.92 (0.8H, d, J=15.6Hz) , 6.18-

6.60 (2H,m) ,6.80-7.35(7.5H,m) ,7.40-8.89 (4H,m)

(308) N- [1- (4-chlorophenyl) -3- (4-fluorophenylthio) -2- propenylidene] -4-chloroaniline (Hereinafter, this compound is referred to as "present compound 308".)

¹ H-NMR(CDCl ₃ ) δ (ppm) :5.95 (0.5H, d, J=15.6Hz) , 6.12-6.75 (2H,m) , 6.87 (0.5H,d, J=15.6Hz) , 6.95-34 (7H,m) , 7.38-7.62 (4H,m)

(309) N- [1- (2 -fluoro-4-chlorophenyl) -3- (4- fluorophenylthio) -2-propenylidene] -4-methylaniline (Hereinafter, this compound is referred to as "present compound 309" .) 1H-NMR(CDCl ₃ ) δ(ppm): 2.20 (1.5H, s) , 2.35 (1.5H, s) ,

6.15(0.5H, d, J=15.3Hz) , 6.37 (0.5H, d, J=15.3Hz) , 6.49(lH,d, J=8.80Hz) , 6.61-6.78(1.5H,m) ,6.86-7.33(8H,m) ,7.40- 7.50 (1.5H,m)

Production Example 313

(1) N- [1- (4-chlorophenyl) -3- (4-fluorophenylthio) -2-methyl- 2-propenylidene] -4-methylaniline (Hereinafter, this compound is referred to as "present compound 310".) (1-1) Into a tetrahydrofuran [THF] solution (20 ml) containing 1- (4-chlorophenyl) -2-methyl-2-propen-l-one (2.1 g) and triethylamine (3 drops) , a THF solution (5 ml) containing 4-fluorothiophenol (1.49 g) was dropped under ice cool and the mixture was stirred at room temperature for 6 hours. The reaction mixture was concentrated under reduced pressure and the resultant residue was subjected to silica gel column chromatography (hexane : ethyl acetate = 15:1) to obtain (4-chlorophenyl) - [2- (4-fluorophenylthio) -1- methylethyl] ketone (3.0 g) .

(2) Into a chloroform solution (50 ml) of the above- described (4-chlorophenyl) - [2- (4-fluorophenylthio) -1- methylethyl] ketone (3.0 g) , p-toluidine (1.04 g) and triethylamine (3.82 g) , titanium tetrachloride (1 M in CH ₂ Cl ₂ , 9.7 ml) was dropped under ice cool and the mixture was stirred at room temperature for 20 hours. The reaction mixture was poured into ice water (200 ml) and insoluble

materials were filtrated off, and the filtrate was partitioned. The chloroform layer was washed with water, dried, and then concentrated under reduced pressure condition to obtain an imine body (3.8 g) .

¹ H-NNR (CDCl ₃ ) δ (ppm) : 1.31 (3H, d, J = 6.7 Hz), 2.22 (3H, s) , 2.93-3.10 (2H, m) , 3.40-3.48 (IH, m) , 6.44-7.40 (12H, m)

(3) To a chloroform solution (50 ml) of the above- described imine body (3.8 g) was added N-chlorosuccinimide (1.33 g) under ice cool and the mixture was stirred at room temperature for 1 hour. The reaction mixture was poured into ice water and washed with water, dried, then, concentrated under reduced pressure condition. To a THF solution (50 ml) of the resultant residue was added DBU (1.73 g) and the mixture was heated under reflux (7 hours) .

After cooling, the deposited material was filtrated off, and the filtrate was concentrated under reduced pressure condition, and the resultant residue was subjected to silica gel column chromatography (hexane : ethyl acetate = 15:1) to obtain the present compound 313 (1.5 g) .

¹ H-NNR (CDCl ₃ ) δ(ppm): 2.21 (3H, d, J = 12.1 Hz), 6.44

(2H, d, J = 8.0 Hz), 6.84-7.03 (6H, m) , 7.14-7.29 (5H, m)

Production Examples 310 to 312, 314 and 315

The following compounds were produced according to the

method of Production Example 313.

(310) N- [1- (2-fluorophenyl) -3- (4-fluorophenylthio) -2- methyl-2-propenylidene] -4-methylaniline (Hereinafter, this compound is referred to as "present compound 310".) 1H-NNR(CDCl ₃ ) δ (pptn) : 2.18(3H,s), 2.26(3H,s), 6.43-

6.56 (3H,m) , 6.83-7.03 (6H,m) ,7.07-7.48 (4H,m)

(311) N- [1- (4-chlorophenyl) -3- (phenylthio) -2-methyl-2- propenylidene] -4-methylaniline (Hereinafter, this compound is referred to as "present compound 311".) 1H-NNR(CDCl ₃ ) δ(ppm): 2.22(3H,s), 2.25(3H,s),

6.45 (2H,d,J=8.2Hz) , 6.58(lH,s), 6.75-7.00 (3H,m) , 7.13 - 7.43 (7H,m)

(312) N- [1- (2-methylphenyl) -3- (phenylthio) -2 -methyl-2- propenylidene] -aniline (Hereinafter, this compound is referred to as "present compound 312".)

¹ H-NNR (DMSO-d ₆ ) δ (ppm) : 1.98(3H,s), 2.17(3H,s), 6.81(2H,d, J=7.5Hz) ,6.88-7.55 (12H,m)

(314) N- [1- (2, 5-difluorophenyl) -3- (4-fluorophenylthio) -2- methyl-2-propenylidene] -4-methylaniline (Hereinafter, this compound is referred to as "present compound 314".) 1H-NNR(CDCl ₃ ) δ(ppm): 2.20 (3H, s) , 2.25 (3H, s) , 6.43- 6.56(3H,m), 6.61-6.69 (lH,m) , 6.82-7.14 (6H,m) , 7.33-

7.32 (2H,m)

(315) N- [1- (2, 4-difluorophenyl) -3- (4-fluorophenylthio) -2- methyl-2-propenylidene] -4-methylaniline (Hereinafter, this

compound is referred to as "present compound 315".) 1H-NNR(CDCl ₃ ) δ(ppm): 2.19 (3H, s) , 2.24 (3H, s) , 6.40- 6.51(3H ₇ Tn), 6.42-6.51 (3H,m) , 6.22-6.75 (2H,m) , 6.85- 7.02(5H,m), 7.22-7.30 (2H,m)

Production Examples 316 to 323

The following compounds were produced according to the method of Production Example 207.

(316) N- [l-cyclohexyl-3- (4-fluorophenylthio) -2- propenylidene] -4-methylaniline (Hereinafter, this compound is referred to as "present compound 316".) 1H-NNR(CDCl ₃ ) δ(ppm): 1.03-1.96 (10H,m) , 2.30-2.40 (4H,m) , 5.79 (0.5H,d, J=15.8Hz) ,6.43-6.50 (1.5H,m) ,6.89-7.33 (6H,m) , 7.44-7.50 (2H,m)

(317) N- [l-tert-butyl-3- (4-fluorophenylthio) -2- propenylidene] -4-methylaniline (Hereinafter, this compound is referred to as "present compound 317".)

¹ H-NNR(CDCl ₃ ) δ(ppm): 1.28(9H,s), 2.30(3H,s), 6.03 (IH, d, J=IO.6Hz), 6.29 (lH,d, J=IO.6Hz) , 6.71-7.30 ( 8H,m)

(318) N- [1- (2-furyl) -3- (4-fluorophenylthio) -2- propenylidene] -4-methylaniline (Hereinafter, this compound is referred to as "present compound 318".) 1H-NMR(CDCl ₃ ) δ(ppm): 2.35 (3H ₇ s) , 5.97 (IH, d, J=15.4Hz) , 6.49-7.60 (12H,m)

(319) N- [1- (3-pyridyl) -3- (4-fluorophenylthio) -2-

propenylidene] -4-methylaniline (Hereinafter, this compound is referred to as "present compound 319".)

¹ H-NMR(CDCl ₃ ) δ (ppm) : 2.35 (3H, s) , 6.12 (IH, d, J=15.6Hz) , 6.36- 7.52(12H,m), 8.65-8.89 (IH, m)

(320) N-[I- (2-thienyl) -3- (4-fluorophenylthio) -2- propenylidene] -4-methylaniline (Hereinafter, this compound is referred to as "present compound 320".) 1H-NMR(CDCl ₃ ) δ (ppm) : 2.35(3H,s), 6.30 (0. IH, d, J=15.2Hz) , 6.22-6.28 (0.3H,m) , 6.48-6.55 (0.3H,m) , 6.62- 7.33 (12.3H,m) , 7.40-7.65 (2H,m)

(321) N- [1- (2-chloro-3-pyridyl) -3- (4-fluorophenylthio) -2- propenylidene] -4-methylaniline (Hereinafter, this compound is referred to as "present compound 321" . ) 1H-NMR(CDCl ₃ ) δ (ppm) : 2.17-2.38 (3H, s) , 6.16-7.56 (12H,m) , 8.27-8.48 (IH, m)

(322) N- [1- (5-chloro-2-thienyl) -3- (4-fluorophenylthio) -2- propenylidene] -4-methylaniline (Hereinafter, this compound is referred to as "present compound 322" . ) 1H-NMR(CDCl ₃ ) δ (ppm) : 2.34 (3H,s), 5.95 (IH, d, J=15.6Hz) , 6.70(2H,d, J=8.2Hz), 6.85-7.33 (9H,m)

(323) N- [1- (5-chloro-3-pyridyl) -3- (4-fluorophenylthio) -2- propenylidene] -4-methylaniline (Hereinafter, this compound is referred to as "present compound 323".) 1H-NMR(CDCl ₃ ) δ(ppm): 2.36(3H,s), 6.09 (IH, d, J=15.2Hz) , 6.33-7.50 (1OH, m) , 7.91-7.97 (IH, m) , 8.62-8.63 (IH, m)

The structures of the present compounds 1 to 309 and 316 to 323 are represented by the following formula.

Combinations of groups represented by Ar ¹ , Ar ² and Ar ³ in the above-described formula are shown in the following table together with the numbers of the present compounds .

Abbreviations shown below have meanings as described below.

Me: methyl group, Et: ethyl group, iPr: isopropyl group, Ph, Phenyl group, In: indanyl group, Np: naphthyl group, Ac: acetyl group

In the table, for example, "4-F-Ph" means a 4fluorophenyl group, "3,4-(Me) ₂ -Ph" means a 3,4- dimethylphenyl group, and "5-In" means a 5-indanyl group.

The structures of the present compounds 310 to 315 are represented by the following formula.

Combinations of groups represented by Ar ¹ , Ar ² and Ar ³ in this formula are shown in the following table together with the numbers of the present compounds .

Abbreviations shown below have meanings same as described above .

Illustrative examples of the compounds of the present invention may include the compounds of the formula (Ia)

In this formula, Ar ^la , Ar ^{2 a} and Ar ^{3 a} are defined as below; [Number ! Ar ^{1 a} , Ar ^{2 a} , Ar ^{3 a} ] =

[1 : Ph, Ph, 2-F-Ph] , [2 ! Ph, Ph, 2-Cl-Ph] , [3 ! Ph, Ph, 2-Br- Ph] , [4 ! Ph, Ph, 3-CF ₃ -Ph] , [5 ! Ph, Ph, 3-MeO-Ph] , [6 ! Ph, Ph, 4-Et-Ph] , [7 : Ph, Ph, 4-EtO-Ph] , [8 ! Ph, Ph, 4-MeS-Ph] , [9 I Ph, Ph, 4-EtS-Ph] , [10 ! Ph, Ph, 4-CN-Ph] , [11 ! Ph, Ph, 4-MeNH-Ph] , [12 ! Ph, Ph, 4-EtNH-Ph] , [13 ! Ph, Ph, 4-AcNH- Ph] , [14 ! Ph, Ph, 4-MeOC (=0) -Ph] , [15 ! Ph, Ph, 4-NH ₂ C (=0)- Ph] , [16 ! Ph, Ph, 4 -MeNHC (=0) -Ph] , [17 ! Ph, Ph, 2,3- (Cl) ₂ - Ph] , [18. ^' Ph, Ph, 2,6-(F) ₂ -Ph] , [19. ^' Ph, Ph, 2,4-(F) ₂ -Ph] ,

ISO

[20 : Ph, Ph, 2,4- (Cl) ₂ -Ph] , [21 ! Ph, Ph, 5-In] , [22 ! Ph, Ph, 2-Np] , [23 ! Ph, Ph, 1-Np] , [24 ! Ph, Ph, 3-Me-2-Np] , [25 ! Ph, 2-F-Ph, 2-F-Ph] , [26 ! Ph, 2-F-Ph, 2-Cl-Ph] , [27 ! Ph, 2-F- Ph, 3-CF ₃ -Ph] , [28 ! Ph, 2-F-Ph, 4-MeS-Ph] , [29 ! Ph, 2-F-Ph, 4-CN-Ph] , [30 ! Ph, 2-F-Ph, 4-AcNH-Ph] , [31 ! Ph, 3-Cl-Ph, 2- F-Ph] , [32 ! Ph, 3-Cl-Ph, 2-Cl-Ph] , [33 ! Ph, 3-Cl-Ph, 3-CF ₃ - Ph] , [34.' Ph, 3-Cl-Ph, 4 -MeS- Ph] , [35 ! Ph, 3-Cl-Ph, 4-CN- Ph] , [36 ! Ph, 3-Cl-Ph, 4 -AcNH- Ph] , [37 ! Ph, 4-F-Ph, 2-F- Ph] , [38 ! Ph, 4-F-Ph, 2-Cl-Ph] , [39 ! Ph, 4-F-Ph, 3-CF ₃ -Ph] ,

[40 ! Ph, 4-F-Ph, 4-MeS-Ph] , [41 ! Ph, 4-F-Ph, 4-CN-Ph] , [42 ! Ph, 4-F-Ph, 4 -AcNH- Ph] , [43 ^' . Ph, 2,3-(Cl) ₂ -Ph, 2-F-Ph] , [44

! Ph, 2,3- (Cl) ₂ -Ph, 2-Cl-Ph] , [45 ! Ph, 2,3-(Cl) ₂ -Ph, 3-CF ₃ - Ph] , [46 ! Ph, 2,3- (Cl) ₂ -Ph, 4-MeS-Ph] , [47 ! Ph, 2,3- (Cl) ₂ - Ph, 4-CN-Ph] , [48 ! Ph, 2,3-(Cl) ₂ -Ph, 4-AcNH-Ph] , [49 ! Ph, 2,4-(F) ₂ -Ph, 2 -F-Ph] , [50 ! Ph, 2,4-(F) ₂ -Ph, 2-Cl-Ph] , [51 ! Ph, 2,4-(F) ₂ -Ph, 3-CF ₃ -Ph] , [52 ! Ph, 2,4-(F) ₂ -Ph, 4-MeS- Ph] , [53 ! Ph, 2,4-(F) ₂ -Ph, 4-CN-Ph] , [54 ! Ph, 2,4-(F) ₂ -Ph, 4 -AcNH- Ph] , [55 ! Ph, 2,6-(F) ₂ -Ph, 2-F-Ph] , [56 ! Ph, 2,6-

(F) ₂ -Ph, 2 -Cl- Ph] , [57 ! Ph, 2,6-(F) ₂ -Ph, 3-CF ₃ -Ph] , [58 ! Ph, 2,6-(F) ₂ -Ph, 4 -MeS-Ph] , [59 ! Ph, 2,6-(F) ₂ -Ph, 4-CN-Ph] ,

[60 ! Ph, 2,6-(F) ₂ -Ph, 4 -AcNH- Ph] , [61 ! Ph, 3,4-(F) ₂ -Ph, 2- F-Ph] , [62 ! Ph, 3,4-(F) ₂ -Ph, 2-Cl-Ph] , [63 ! Ph, 3,4-(F) ₂ - Ph, 3-CF ₃ -Ph] , [64 ! Ph, 3,4-(F) ₂ -Ph, 4-MeS-Ph] , [65 ! Ph, 3,4-(F) ₂ -Ph, 4-CN-Ph] , [66 ! Ph, 3,4-(F) ₂ -Ph, 4 -AcNH- Ph] ,

[67 ! Ph, 3,5-(F) ₂ -Ph, 2-F-Ph] , [68 ! Ph, 3,5-(F) ₂ -Ph, 2-C1-

Ph] , [69 ! Ph, 3,5-(F) ₂ -Ph, 3-CF ₃ -Ph] , [70 I Ph, 3,5-(F) ₂ -Ph, 4-MeS-Ph] , [71 I Ph, 3,5-(F) ₂ -Ph, 4 -CN-Ph] , [72 ! Ph, 3,5- (F) ₂ -Ph, 4 -AcNH- Ph] , [73 ! Ph, 4-Et-Ph, Ph] , [74 ! Ph, 4-EtO- Ph, Ph] , [75 ! Ph, 4-MeS-Ph, Ph] , [76 ! Ph, 4-EtS-Ph, Ph] , [77 ! Ph, 4-CN-Ph, Ph] , [78 ! Ph, 4-MeNH-Ph, Ph] , [79 ! Ph, 4- EtNH-Ph, Ph] , [80 ! Ph, 4-AcNH-Ph, Ph] , [81 ! Ph, 4-MeOC (=0) - Ph, Ph] , [82 ! Ph, 4-NH ₂ C (=0) -Ph, Ph] , [83 ! Ph, 4-MeNHC(=O)- Ph, Ph] , [84 ! Ph, 5-Iru Ph] , [85. ^" Ph, 2 -Np, Ph] , [86 ! Ph, 1- Np, Ph] , [87 ! Ph, 3-Me-2-Np, Ph] , [88 ! 2-F-Ph, 4-Et-Ph, Ph] , [89 ! 2-F-Ph, 4-Et-Ph, 3-F-Ph] , [90 ! 2-F-Ph, 4-Et-Ph, 3-Me-Ph] , [91 ! 2-F-Ph, 4-Et-Ph, 4-F-Ph] , [92 ! 2-F-Ph, 4-Et- Ph, 4-Me-Ph] , [93 ! 2-F-Ph, 4-Et-Ph, 4-CF ₃ -Ph] , [94 ! 2-F-Ph, 4-Et-Ph, 4-Ph, Ph] , [95 ! 2-F-Ph, 4-Et-Ph, 3,4-(Me) ₂ -Ph] , [96 ! 2-F-Ph, 4-Et-Ph, 5-In] , [97 ! 2-F-Ph, 4-EtS-Ph, Ph] , [98 ! 2-F-Ph, 4-EtS-Ph, 3-F-Ph] , [99 ! 2-F-Ph, 4-EtS-Ph, 3- Me-Ph] , [100 ! 2-F-Ph, 4-EtS-Ph, 4-F-Ph] , [101 ! 2-F-Ph, 4- EtS-Ph, 4-Me-Ph] , [102 ! 2-F-Ph, 4-EtS-Ph, 4-CF ₃ -Ph] , [103 ! 2-F-Ph, 4-EtS-Ph, 4-Ph, Ph] , [104 ! 2-F-Ph, 4-EtS-Ph, 3,4- (Me) ₂ -Ph] , [105 ! 2-F-Ph, 4-EtS-Ph, 5-In] , [106 ! 2-F-Ph, 4- CN-Ph, Ph] , [107 ! 2-F-Ph, 4-CN-Ph, 3-F-Ph] , [108 ! 2-F-Ph, 4-CN-Ph, 3-Me-Ph] , [109 ! 2-F-Ph, 4-CN-Ph, 4-F-Ph] , [110 ! 2- F-Ph, 4-CN-Ph, 4-Me-Ph] , [111 ! 2-F-Ph, 4-CN-Ph, 4-CF ₃ -Ph] , [112 ! 2-F-Ph, 4-CN-Ph, 4-Ph, Ph] , [113 ! 2-F-Ph, 4-CN-Ph, 3,4-(Me) ₂ -Ph] , [114 ! 2-F-Ph, 4-CN-Ph, 5-In] , [115 ! 2-F-Ph, 4-AcNH-Ph, Ph] , [116 ! 2-F-Ph, 4-AcNH-Ph, 3-F-Ph] , [117 ! 2-

F-Ph, 4-AcNH-Ph, 3-Me-Ph] , [118 ^' .2-F-Ph, 4-AcNH-Ph, 4-F- Ph] , [119 : 2-F-Ph, 4-AcNH-Ph, 4-Me-Ph] , [120 ^' .2-F-Ph, 4- AcNH-Ph, 4-CF ₃ -Ph] , [121 ! 2-F-Ph, 4-AcNH-Ph, 4-Ph, Ph] , [122 ! 2-F-Ph, 4-AcNH-Ph, 3,4-(Me) ₂ -Ph] , [123 ! 2-F-Ph, 4- AcNH-Ph, 5-In] , [124 ! 2-F-Ph, 5-Iru Ph] , [125 ! 2-F-Ph, 5-In, 3-F-Ph] , [126 ! 2-F-Ph, 5-In, 3-Me-Ph] , [127 ! 2-F-Ph, 5-In, 4-F-Ph] , [128 ! 2-F-Ph, 5-In, 4-Me-Ph] , [129 ! 2-F-Ph, 5-In, 4-CF ₃ -Ph] , [130 ! 2-F-Ph, 5-In, 4-Ph, Ph] , [131 ! 2-F-Ph, 5- In, 3,4-(Me) ₂ -Ph] , [132 ! 2-F-Ph, 5-In _% 5-In] , [133 ! 2-F-Ph ₇ 1-Np, Ph] , [134 ! 2-F-Ph, 1-Np _> 3-F-Ph] , [135 ! 2-F-Ph, 1-^ 3-Me-Ph] , [136 ! 2-F-Ph, 1-Np, 4-F-Ph] , [137 ! 2-F-Ph, 1-Np, 4-Me-Ph] , [138 ! 2-F-Ph, 1-Np, 4-CF ₃ -Ph] , [139 ! 2-F-Ph, 1- Np, 4-Ph, Ph] , [140 ! 2-F-Ph, 1-Np _^ 3,4-(Me) ₂ -Ph] , [141 ! 2-F- Ph, 1-Np _^ 5-In] , [142 ! 2-F-Ph, 3-Me-2-Np, Ph] , [143 ! 2-F-Ph, 3-Me-2-Np _λ 3-F-Ph] , [144 ! 2-F-Ph, 3-Me-2-Np _> 3-Me-Ph] , [145 ! 2-F-Ph, 3-Me-2-Np, 4-F-Ph] , [146 ! 2-F-Ph, 3-Me-2-Np, 4- Me-Ph] , [147 ! 2-F-Ph, 3-Me-2-Np, 4-CF ₃ -Ph] , [148.' 2-F-Ph, 3-Me-2-Np, 4-Ph, Ph] , [149 ! 2-F-Ph, 3-Me-2-Np _^ 3,4- (Me) ₂ - Ph] , [150 ! 2-F-Ph, 3-Me-2-Np _> 5-In] , [151. ^' 2-Cl-Ph, 2-F-Ph, 2-F-Ph] , [152 ! 2-Cl-Ph, 2-F-Ph, 2-Cl-Ph] , [153 ! 2-Cl-Ph, 2- F-Ph, 3-CF ₃ -Ph] , [154 ! 2-Cl-Ph, 2-F-Ph, 4 -MeS-Ph] , [155 ! 2- Cl-Ph, 2-F-Ph, 4-CN-Ph] , [156 ! 2-Cl-Ph, 2-F-Ph, 4-AcNH-Ph] , [157 ! 2-Cl-Ph, 3-Cl-Ph, 2-F-Ph] , [158 ! 2-Cl-Ph, 3-Cl-Ph, 2- Cl-Ph] , [159 ! 2-Cl-Ph, 3-Cl-Ph, 3-CF ₃ -Ph] , [160 ! 2-Cl-Ph, 3-Cl-Ph, 4-MeS-Ph] , [161 ! 2-Cl-Ph, 3-Cl-Ph, 4 -CN-Ph] , [162

: 2-Cl-Ph, 3-Cl-Ph, 4-AcNH-Ph] , [163 ! 2-Cl-Ph, 4-F-Ph, 2-F- Ph] , [164 : 2-Cl-Ph, 4-F-Ph, 2-Cl-Ph] , [165 ! 2-Cl-Ph, 4-F- Ph, 3-CF ₃ -Ph] , [166 ! 2-Cl-Ph, 4-F-Ph, 4-MeS-Ph] , [167 ! 2- Cl-Ph, 4-F-Ph, 4-CN-Ph] , [168 ! 2-Cl-Ph, 4-F-Ph, 4-AcNH-Ph] , [169 ! 2-Cl-Ph, 2,3-(Cl) ₂ -Ph, 2-F-Ph] , [170 ! 2-Cl-Ph, 2,3- (Cl) ₂ -Ph, 2-Cl-Ph] , [171 ! 2-Cl-Ph, 2,3-(Cl) ₂ -Ph, 3-CF ₃ -Ph] , [172 ! 2-Cl-Ph, 2,3- (Cl) ₂ -Ph, 4 -MeS- Ph] , [173. ^' 2-Cl-Ph, 2,3- (Cl) ₂ -Ph, 4 -CN-Ph] , [174 ! 2-Cl-Ph, 2,3-(Cl) ₂ -Ph, 4-AcNH- Ph] , [175 ! 2-Cl-Ph, 2,4-(F) ₂ -Ph, 2-F-Ph] ₁ [176 ! 2-Cl-Ph, 2,4-(F) ₂ -Ph, 2-Cl-Ph] , [177 ! 2-Cl-Ph, 2,4-(F) ₂ -Ph, 3-CF ₃ - Ph] , [178 ! 2-Cl-Ph, 2,4-(F) ₂ -Ph, 4-MeS-Ph] , [179 ! 2-Cl-Ph, 2,4-(F) ₂ -Ph, 4 -CN-Ph] , [180 ! 2-Cl-Ph, 2,4-(F) ₂ -Ph, 4-AcNH- Ph] , [181 ! 2-Cl-Ph, 2,6-(F) ₂ -Ph, 2-F-Ph] , [182 ! 2-Cl-Ph, 2,6-(F) ₂ -Ph, 2-Cl-Ph] , [183 ! 2-Cl-Ph, 2,6-(F) ₂ -Ph, 3-CF ₃ - Ph] , [184 ! 2-Cl-Ph, 2,6-(F) ₂ -Ph, 4-MeS-Ph] , [185 ! 2-Cl-Ph, 2,6-(F) ₂ -Ph, 4 -CN-Ph] , [186 ! 2-Cl-Ph, 2,6-(F) ₂ -Ph, 4-AeNH- Ph] , [187 ! 2-Cl-Ph, 3,4-(F) ₂ -Ph, 2-F-Ph] , [188.' 2-Cl-Ph, 3,4-(F) ₂ -Ph, 2-Cl-Ph] , [189 ! 2-Cl-Ph, 3,4-(F) ₂ -Ph, 3-CF ₃ - Ph] , [190.' 2-Cl-Ph, 3,4-(F) ₂ -Ph, 4 -MeS- Ph] , [191 ! 2-Cl-Ph, 3,4-(F) ₂ -Ph, 4 -CN-Ph] , [192 ! 2-Cl-Ph, 3,4-(F) ₂ -Ph, 4-AcNH- Ph] , [193 ! 2-Cl-Ph, 3,5-(F) ₂ -Ph, 2 -F-Ph] , [194 ! 2-Cl-Ph, 3,5-(F) ₂ -Ph, 2-Cl-Ph] , [195 ! 2-Cl-Ph, 3,5-(F) ₂ -Ph, 3-CF ₃ - Ph] , [196 ! 2-Cl-Ph, 3,5-(F) ₂ -Ph, 4 -MeS-Ph] , [197 ! 2-Cl-Ph, 3,5-(F) ₂ -Ph, 4 -CN- Ph] , [198 ! 2-Cl-Ph, 3,5-(F) ₂ -Ph, 4-AcNH- Ph] , [199 ! 3-Cl-Ph, 2-F-Ph, 2-F-Ph] , [200 ! 3-Cl-Ph, 2-F-Ph,

2-Cl-Ph] , [201 ! 3-Cl-Ph, 2-F-Ph, 3-CF ₃ -Ph] , [202 ! 3-Cl-Ph, 2-F-Ph, 4-MeS-Ph] , [203 ! 3-Cl-Ph, 2-F-Ph, 4 -CN-Ph] , [204 ! 3-Cl-Ph, 2-F-Ph, 4-AcNH-Ph] , [205 ! 3-Cl-Ph, 3-Cl-Ph, 2-F- Ph] , [206 ! 3-Cl-Ph, 3-Cl-Ph, 2-Cl-Ph] , [207 ! 3-Cl-Ph, 3-Cl- Ph, 3-CF ₃ -Ph] , [208 ! 3-Cl-Ph, 3-Cl-Ph, 4 -MeS- Ph] , [209 ! 3- Cl-Ph, 3-Cl-Ph, 4-CN-Ph] , [210 ! 3-Cl-Ph, 3-Cl-Ph, 4-AcNH- Ph] , [211 ! 3-Cl-Ph, 4-F-Ph, 2-F-Ph] , [212 ! 3-Cl-Ph, 4-F-Ph, 2-Cl-Ph] , [213 ! 3-Cl-Ph, 4-F-Ph, 3-CF ₃ -Ph] , [214. ^' 3-Cl-Ph, 4-F-Ph, 4-MeS-Ph] , [215 ! 3-Cl-Ph, 4-F-Ph, 4-CN-Ph] , [216 ! 3-Cl-Ph, 4-F-Ph, 4-AcNH-Ph] , [217 ! 3-Cl-Ph, 2,3-(Cl) ₂ -Ph, 2-F-Ph] , [218 ! 3-Cl-Ph, 2,3-(Cl) ₂ -Ph, 2-Cl-Ph] , [219 ! 3-Cl- Ph, 2,3- (Cl) ₂ -Ph, 3-CF ₃ -Ph] , [220 ! 3-Cl-Ph, 2,3-(Cl) ₂ -Ph, 4 -MeS- Ph] , [221 ! 3-Cl-Ph, 2,3-(Cl) ₂ -Ph, 4-CN-Ph] , [222 ! 3- Cl-Ph, 2,3- (Cl) ₂ -Ph, 4 -AcNH- Ph] , [223 ! 3-Cl-Ph, 2,4- (F) ₂ - Ph, 2-F-Ph] , [224 ! 3-Cl-Ph, 2,4-(F) ₂ -Ph, 2-Cl-Ph] , [225 ! 3- Cl-Ph, 2,4-(F) ₂ -Ph, 3-CF ₃ -Ph] , [226 ! 3-Cl-Ph, 2,4-(F) ₂ -Ph, 4-MeS-Ph] , [227 ! 3-Cl-Ph, 2,4-(F) ₂ -Ph, 4-CN-Ph] , [228 ! 3- Cl-Ph, 2,4-(F) ₂ -Ph, 4 -AcNH- Ph] , [229 ! 3-Cl-Ph, 2,6-(F) ₂ -Ph, 2-F-Ph] , [230 ! 3-Cl-Ph, 2,6-(F) ₂ -Ph, 2-Cl-Ph] , [231 ! 3-Cl- Ph, 2,6-(F) ₂ -Ph, 3-CF ₃ -Ph] , [232 ! 3-Cl-Ph, 2,6-(F) ₂ -Ph, 4- MeS-Ph] , [233 ! 3-Cl-Ph, 2,6-(F) ₂ -Ph, 4-CN-Ph] , [234 ! 3-Cl- Ph, 2,6-(F) ₂ -Ph, 4 -AcNH-Ph] , [235 ! 3-Cl-Ph, 3,4-(F) ₂ -Ph, 2- F-Ph] , [236 ! 3-Cl-Ph, 3,4-(F) ₂ -Ph, 2 -Cl-Ph] , [237 ! 3-Cl-Ph, 3,4-(F) ₂ -Ph, 3-CF ₃ -Ph] , [238 ! 3-Cl-Ph, 3,4-(F) ₂ -Ph, 4-MeS- Ph] , [239 ! 3-Cl-Ph, 3,4-(F) ₂ -Ph, 4-CN-Ph] , [240 ! 3-Cl-Ph,

3,4-(F) ₂ -Ph, 4 -AcNH- Ph] , [241 ! 3-Cl-Ph, 3,5-(F) ₂ -Ph, 2-F- Ph] , [242 ! 3-Cl-Ph, 3,5-(F) ₂ -Ph, 2-Cl-Ph] , [243 ! 3-Cl-Ph, 3,5-(F) ₂ -Ph, 3-CF ₃ -Ph] , [244 ! 3-Cl-Ph, 3,5-(F) ₂ -Ph, 4-MeS- Ph] , [245 ! 3-Cl-Ph, 3,5-(F) ₂ -Ph, 4-CN-Ph] , [246 '.3-Cl-Ph, 3,5-(F) ₂ -Ph, 4 -AcNH- Ph] , [247 ! 3-CF ₃ -Ph, 4-Et-Ph, Ph] , [248

! 3-CF ₃ -Ph, 4-Et-Ph, 3-F-Ph] , [249 ! 3-CF ₃ -Ph, 4-Et-Ph, 3- Me-Ph] , [250. ^' 3-CF ₃ -Ph, 4-Et-Ph, 4-F-Ph] , [251 ! 3-CF ₃ -Ph, 4-Et-Ph, 4-Me-Ph] , [252. ^' 3-CF ₃ -Ph, 4-Et-Ph, 4-CF ₃ -Ph] , [253

! 3-CF ₃ -Ph, 4-Et-Ph, 4-Ph, Ph] , [254 ! 3-CF ₃ -Ph, 4-Et-Ph, 3,4-(Me) ₂ -Ph] , [255 ! 3-CF ₃ -Ph, 4-Et-Ph ₇ 5-In] , [256 ! 3-CF ₃ - Ph, 4-EtS-Ph, Ph] , [257 ! 3-CF ₃ -Ph, 4-EtS-Ph, 3-F-Ph] , [258

! 3-CF ₃ -Ph, 4-EtS-Ph, 3-Me-Ph] , [259 ! 3-CF ₃ -Ph, 4-EtS-Ph, 4-F-Ph] , [260 ! 3-CF ₃ -Ph, 4-EtS-Ph, 4-Me-Ph] , [261 ! 3-CF ₃ - Ph, 4-EtS-Ph, 4-CF ₃ -Ph] , [262 ! 3-CF ₃ -Ph, 4-EtS-Ph, 4-Ph, Ph] , [263 ! 3-CF ₃ -Ph, 4-EtS-Ph, 3,4-(Me) ₂ -Ph] , [264 ! 3-CF ₃ - Ph, 4-EtS-Ph, 5-In] , [265 ! 3-CF ₃ -Ph, 4-CN-Ph, Ph] , [266 ! 3- CF ₃ -Ph, 4-CN-Ph, 3-F-Ph] , [267 ! 3-CF ₃ -Ph, 4-CN-Ph, 3-Me- Ph] , [268. ^' 3-CF ₃ -Ph, 4-CN-Ph, 4-F-Ph] , [269 ! 3-CF ₃ -Ph, 4- CN-Ph, 4-Me-Ph] , [270. ^' 3-CF ₃ -Ph, 4-CN-Ph, 4-CF ₃ -Ph] , [271 ! 3-CF ₃ -Ph, 4-CN-Ph, 4-Ph, Ph] , [272. ^' 3-CF ₃ -Ph, 4-CN-Ph, 3,4-

(Me) ₂ -Ph] , [273 ! 3-CF ₃ -Ph ₇ 4-CN-Ph, 5-In] , [274 ! 3-CF ₃ -Ph, 4-AcNH-Ph, Ph] , [275 ! 3-CF ₃ -Ph, 4-AcNH-Ph, 3-F-Ph] , [276 ! 3-CF ₃ -Ph, 4-AcNH-Ph, 3-Me-Ph] , [277 ! 3-CF ₃ -Ph, 4-AcNH-Ph, 4-F-Ph] , [278 ! 3-CF ₃ -Ph, 4-AcNH-Ph, 4-Me-Ph] , [279 ! 3-CF ₃ - Ph, 4-AcNH-Ph, 4-CF ₃ -Ph] , [280 ! 3-CF ₃ -Ph, 4-AcNH-Ph, 4-Ph,

Ph] , [281 ! 3-CF ₃ -Ph, 4-AcNH-Ph, 3,4-(Me) ₂ -Ph] , [282 ! 3-CF ₃ - Ph, 4-AcNH-Ph, 5-In] , [283 ! 3-CF ₃ -Ph, 5-In _> Ph] , [284 ! 3- CF ₃ -Ph, 5-In, 3-F-Ph] , [285 ! 3-CF ₃ -Ph, 5-In, 3-Me-Ph] , [286

! 3-CF ₃ -Ph, 5-In, 4-F-Ph] , [287 ! 3-CF ₃ -Ph, 5-In, 4-Me-Ph] ,

[288 ! 3-CF ₃ -Ph, 5-In, 4-CF ₃ -Ph] , [289 ! 3-CF ₃ -Ph, 5-In, 4- Ph, Ph] , [290 ! 3-CF ₃ -Ph, 5-In, 3,4-(Me) ₂ -Ph] , [291 ! 3-CF ₃ - Ph, 5-In,, 5-In] , [292 ! 3-CF ₃ -Ph, 1-Np, Ph] , [293. ^' 3-CF ₃ -Ph, 1-Np,, 3-F-Ph] , [294 ! 3-CF ₃ -Ph, 1-Np,, 3-Me-Ph] , [295 ! 3-CF ₃ - Ph ₇ 1-Np, 4-F-Ph] , [296 ! 3-CF ₃ -Ph, 1-Np, 4-Me-Ph] , [297 ! 3- CF ₃ -Ph, 1-Np, 4-CF ₃ -Ph] , [298 ! 3-CF ₃ -Ph, 1-Np, 4-Ph, Ph] ,

[299 ! 3-CF ₃ -Ph, l-Np _λ 3,4-(Me) ₂ -Ph] , [300 ! 3-CF ₃ -Ph, 1-Np _> 5-In] , [301 ! 3-CF ₃ -Ph, 3-Me-2-Np, Ph] , [302 ! 3-CF ₃ -Ph, 3- Me-2-Np _N 3-F-Ph] , [303 ! 3-CF ₃ -Ph, 3-Me-2-Np _λ 3-Me-Ph] , [304

! 3-CF ₃ -Ph, 3-Me-2-Np, 4-F-Ph] , [305 ! 3-CF ₃ -Ph, 3-Me-2-Np, 4-Me-Ph] , [306 ! 3-CF ₃ -Ph, 3-Me-2-Np, 4-CF ₃ -Ph] , [307 ! 3- CF ₃ -Ph, 3-Me-2-Np, 4-Ph, Ph] , [308 ! 3-CF ₃ -Ph, 3-Me-2-Np _^ 3,4-(Me) ₂ -Ph] , [309 ! 3-CF ₃ -Ph, 3-Me-2-Np _> 5-In] , [310.4-F- Ph, 2-F-Ph, 2 -F- Ph] , [311 ! 4-F-Ph, 2-F-Ph, 2-Cl-Ph] , [312 ! 4-F-Ph, 2-F-Ph, 3-CF ₃ -Ph] , [313. ^' 4-F-Ph, 2-F-Ph, 4 -MeS-Ph] ,

[314 ! 4-F-Ph, 2-F-Ph, 4-CN-Ph] , [315 ! 4-F-Ph, 2-F-Ph, 4- AcNH-Ph] , [316 ! 4-F-Ph, 3-Cl-Ph, 2-F-Ph] , [317 ! 4-F-Ph, 3- Cl-Ph, 2 -Cl-Ph] , [318 ! 4-F-Ph, 3-Cl-Ph, 3-CF ₃ -Ph] , [319.4- F-Ph, 3-Cl-Ph, 4 -MeS- Ph] , [320 ! 4-F-Ph, 3-Cl-Ph, 4 -CN-Ph] ,

[321 ! 4-F-Ph, 3-Cl-Ph ₇ 4-AcNH-Ph] , [322 ! 4-F-Ph, 4-F-Ph, 2- F-Ph] , [323 ! 4-F-Ph, 4-F-Ph, 2-Cl-Ph] , [324 ! 4-F-Ph, 4-F-

Ph, 3-CF ₃ -Ph] , [325 ! 4-F-Ph, 4-F-Ph, 4 -MeS-Ph] , [326 ! 4-F- Ph, 4-F-Ph, 4-CN-Ph] , [327 ! 4-F-Ph, 4-F-Ph, 4-AcNH-Ph] , [328 !4-F-Ph, 2,3-(Cl) ₂ -Ph, 2-F-Ph] , [329 ! 4-F-Ph, 2,3- (Cl) ₂ -Ph, 2-Cl-Ph] , [330 ! 4-F-Ph, 2,3-(Cl) ₂ -Ph, 3-CF ₃ -Ph] , [331 ! 4-F-Ph, 2,3- (Cl) ₂ -Ph, 4-MeS-Ph] , [332 ! 4-F-Ph, 2,3- (Cl) ₂ -Ph, 4 -CN- Ph] , [333. ^' 4-F-Ph, 2,3-(Cl) ₂ -Ph, 4 -AcNH- Ph] , [334.'4-F-Ph, 2,4-(F) ₂ -Ph, 2 - P- Ph] , [335.' 4-F-Ph, 2,4- (F) ₂ - Ph, 2-Cl-Ph] , [336 ! 4-F-Ph, 2,4-(F) ₂ -Ph, 3-CF ₃ -Ph], [337 ! 4-F-Ph, 2,4-(F) ₂ -Ph, 4-MeS-Ph] ₇ [338 ! 4-F-Ph, 2,4-(F) ₂ -Ph, 4 -CN-Ph] , [339 ! 4-F-Ph, 2,4-(F) ₂ -Ph, 4 -AcNH- Ph] , [340 ! 4-F- Ph, 2,6-(F) ₂ -Ph, 2 -F- Ph] , [341 ! 4-F-Ph, 2,6-(F) ₂ -Ph, 2-C1- Ph] , [342 ! 4-F-Ph, 2,6-(F) ₂ -Ph, 3-CF ₃ -Ph] , [343 ! 4-F-Ph, 2,6-(F) ₂ -Ph, 4-MeS-Ph] , [344 ! 4-F-Ph, 2,6-(F) ₂ -Ph, 4-CN- Ph] , [345 !4-F-Ph, 2,6-(F) ₂ -Ph, 4 -AcNH- Ph] , [346 !4-F-Ph, 3,4-(F) ₂ -Ph, 2-F-Ph] , [347 ! 4-F-Ph, 3,4-(F) ₂ -Ph, 2 -Cl-Ph] , [348 ! 4-F-Ph, 3,4-(F) ₂ -Ph, 3-CF ₃ -Ph] , [349 ! 4-F-Ph, 3,4- (F) ₂ -Ph, 4-MeS-Ph] , [350.' 4-F-Ph, 3,4-(F) ₂ -Ph, 4 -CN- Ph] , [351. ^' 4-F-Ph, 3,4-(F) ₂ -Ph, 4 -AcNH- Ph] , [352.' 4-F-Ph, 3,5- (F) ₂ -Ph, 2-F-Ph], [353 ! 4-F-Ph, 3,5-(F) ₂ -Ph, 2 -Cl -Ph] , [354 ! 4-F-Ph, 3,5-(F) ₂ -Ph, 3-CF ₃ -Ph] ₇ [355 !4-F-Ph ₇ 3,5-(F) ₂ - Ph, 4-MeS-Ph] , [356 ! 4-F-Ph, 3,5-(F) ₂ -Ph, 4 -CN-Ph] , [357 ! 4-F-Ph, 3,5-(F) ₂ -Ph, 4 -AcNH-Ph] , [358 ! 4-Me-Ph, 4-Et-Ph, Ph] , [359 ! 4-Me-Ph, 4-Et-Ph, 3 -P-Ph] , [360 ! 4-Me-Ph, 4-Et- Ph, 3-Me-Ph] , [361 ! 4-Me-Ph, 4-Et-Ph, 4-F-Ph] , [362 ! 4-Me- Ph, 4-Et-Ph, 4-Me-Ph] , [363 ! 4-Me-Ph, 4-Et-Ph, 4-CF ₃ -Ph] ,

[364 : 4-Me-Ph, 4-Et-Ph, 4-Ph, Ph] , [365 ! 4-Me-Ph, 4-Et-Ph, 3,4-(Me) ₂ -Ph] , [366 ! 4-Me-Ph, 4-Et-Ph, 5-In] , [367 ! 4-Me- Ph, 4-EtS-Ph, Ph] , [368 ! 4-Me-Ph, 4-EtS-Ph, 3-F-Ph] , [369 ! 4-Me-Ph, 4-EtS-Ph, 3-Me-Ph] , [370 ! 4-Me-Ph, 4-EtS-Ph, 4-F- Ph] , [371 : 4-Me-Ph, 4-EtS-Ph, 4-Me-Ph] , [372 ! 4-Me-Ph, 4- EtS-Ph, 4-CF ₃ -Ph] , [37314-Me-Ph, 4-EtS-Ph, 4-Ph, Ph] , [374

; 4-Me-Ph, 4-EtS-Ph, 3,4-(Me) ₂ -Ph] , [375.' 4-Me-Ph, 4-EtS- Ph, 5-In] , [376.' 4-Me-Ph, 4-CN-Ph, Ph] , [377 ! 4-Me-Ph, 4- CN-Ph, 3-F-Ph] ₇ [378 ! 4-Me-Ph, 4-CN-Ph, 3-Me-Ph], [379 ! 4- Me-Ph, 4-CN-Ph, 4-F-Ph] , [380 ! 4-Me-Ph, 4-CN-Ph, 4-Me-Ph] ,

[381 ! 4-Me-Ph, 4-CN-Ph, 4-CF ₃ -Ph] , [382 ! 4-Me-Ph, 4-CN-Ph, 4-Ph, Ph] , [383 ! 4-Me-Ph, 4-CN-Ph, 3,4-(Me) ₂ -Ph] , [384 ! 4- Me-Ph, 4-CN-Ph, 5-In] , [385 ! 4-Me-Ph, 4-AcNH-Ph, Ph] , [386

! 4-Me-Ph, 4-AcNH-Ph, 3-F-Ph] , [387 ! 4-Me-Ph, 4-AcNH-Ph, 3- Me-Ph] , [388 ! 4-Me-Ph, 4-AcNH-Ph, 4-F-Ph] , [389 ! 4-Me-Ph, 4-AcNH-Ph, 4-Me-Ph] , [390 ! 4-Me-Ph, 4-AcNH-Ph, 4-CF ₃ -Ph] ,

[391 ! 4-Me-Ph, 4-AcNH-Ph, 4-Ph, Ph] , [392 ! 4-Me-Ph, 4-AcNH- Ph, 3,4-(Me) ₂ -Ph] , [393 ! 4-Me-Ph, 4-AcNH-Ph, 5-In] , [394 ! 4-Me-Ph, 5-In _λ Ph] , [395 ! 4-Me-Ph, 5-In, 3-F-Ph] , [396 ! 4- Me-Ph, 5-In ₇ 3-Me-Ph] , [397 ! 4-Me-Ph, 5-In, 4-F-Ph] , [398 ! 4-Me-Ph, 5-In, 4-Me-Ph] , [399 ! 4-Me-Ph, 5-In, 4-CF ₃ -Ph] ,

[400 ! 4-Me-Ph, 5-In, 4-Ph, Ph] , [401 ! 4-Me-Ph, 5-In, 3,4-

(Me) ₂ -Ph] , [402 ! 4-Me-Ph, 5-Iα, 5-In] , [403 ! 4-Me-Ph, 1-Np, Ph] , [404 ! 4-Me-Ph, 1-Np^ 3-F-Ph] , [405 ! 4-Me-Ph, 1-Np^ 3- Me-Ph] , [406 ! 4-Me-Ph, 1-Np, 4-F-Ph] , [407 ! 4-Me-Ph, 1-Np,

4-Me-Ph] , [408 : 4-Me-Ph, 1-Np, 4-CF ₃ -Ph] , [409 ! 4-Me-Ph, 1- Np, 4-Ph, Ph] , [410 ! 4-Me-Ph, 1-Np _% 3,4-(Me) ₂ -Ph] , [411.4- Me-Ph, 1-Np _> 5-In] , [412 I 4-Me-Ph, 3-Me~2-Np, Ph] , [413 I 4- Me-Ph, 3-Me-2-Np _^ 3-F-Ph] , [414 ! 4-Me-Ph, 3-Me-2-Np _λ 3-Me- Ph] , [415 ! 4-Me-Ph, 3-Me-2-Np, 4-F-Ph] , [416 ! 4-Me-Ph, 3- Me-2-Np, 4-Me-Ph] , [417 ! 4-Me-Ph, 3-Me-2-Np, 4-CF ₃ -Ph] ,

[418. ^" 4-Me-Ph, 3-Me-2-Np, 4-Ph, Ph] , [419 ! 4-Me-Ph, 3-Me-2- Np, 3,4-(Me) ₂ -Ph] , [420 ! 4-Me-Ph, 3-Me-2-Np, 5-In] , [421 ! 2,4- (Cl) ₂ -Ph, 2-F-Ph, 2-F-Ph] ₇ [422 ! 2,4-(Cl) ₂ -Ph, 2-F-Ph, 2-Cl-Ph] ₇ [423 ! 2,4-(Cl) ₂ -Ph, 2-F-Ph, 3-CF ₃ -Ph] ₇ [424 ! 2,4-

(Cl) ₂ -Ph, 2-F-Ph, 4 -MeS-Ph] , [425 ! 2,4-(Cl) ₂ -Ph, 2-F-Ph, 4- CN-Ph] , [426 ! 2,4-(Cl) ₂ -Ph, 2-F-Ph, 4-AcNH-Ph] , [427 ! 2,4-

(Cl) ₂ -Ph, 3-Cl-Ph ₇ 2-F-Ph] ₇ [428 ! 2,4-(Cl) ₂ -Ph, 3-Cl-Ph, 2- Cl-Ph] , [429 ! 2,4-(Cl) ₂ -Ph, 3-Cl-Ph, 3-CF ₃ -Ph] , [430 ! 2,4-

(Cl) ₂ -Ph, 3-Cl-Ph ₇ 4-MeS-Ph] , [431 ! 2,4-(Cl) ₂ -Ph, 3-Cl-Ph, 4 -CN-Ph] , [432 ! 2,4-(Cl) ₂ -Ph, 3-Cl-Ph, 4-AcNH-Ph] , [433 ! 2,4- (Cl) ₂ -Ph, 4-F-Ph, 2-F-Ph] , [434. ^' 2,4-(Cl) ₂ -Ph, 4-F-Ph, 2-Cl-Ph] , [435 ! 2,4-(Cl) ₂ -Ph, 4-F-Ph, 3-CF ₃ -Ph] ₇ [436 ! 2,4-

(Cl) ₂ -Ph ₇ 4-F-Ph ₇ 4-MeS-Ph] ₇ [437 ! 2, 4- (Cl) ₂ -Ph ₇ 4-F-Ph, 4- CN-Ph] , [438 ! 2,4-(Cl) ₂ -Ph ₇ 4-F-Ph, 4-AcNH-Ph] , [439 ! 2,4-

(Cl) ₂ -Ph, 2,3- (Cl) ₂ -Ph, 2-F-Ph] , [440 ! 2,4-(Cl) ₂ -Ph, 2,3-

(Cl) ₂ -Ph, 2-Cl-Ph] ₇ [441 ! 2,4-(Cl) ₂ -Ph ₇ 2,3-(Cl) ₂ -Ph ₇ 3- CF ₃ -Ph] , [442 ! 2,4-(Cl) ₂ -Ph, 2,3-(Cl) ₂ -Ph, 4 -MeS- Ph] , [443

! 2,4-(Cl) ₂ -Ph ₇ 2,3- (Cl) ₂ -Ph, 4 -CN-Ph] , [444 ! 2,4-(Cl) ₂ -Ph ₇ 2,3- (Cl) ₂ -Ph ₇ 4 -AcNH- Ph] , [445 ! 2,4-(Cl) ₂ -Ph, 2,4-(F) ₂ -Ph,

2-F-Ph] , [446 ! 2,4- (Cl) ₂ -Ph, 2,4- (F) ₂ -Ph, 2-Cl-Ph] , [447 ! 2,4- (Cl) ₂ -Ph, 2,4- (F) ₂ -Ph, 3-CF ₃ -Ph] , [448 ! 2,4- (Cl) ₂ -Ph, 2,4- (F) ₂ -Ph, 4 -MeS- Ph] , [449 ! 2,4- (Cl) ₂ -Ph, 2,4- (F) ₂ -Ph, 4- CN-Ph] , [450 ! 2,4- (Cl) ₂ -Ph, 2,4- (F) ₂ -Ph, 4 -AcNH-Ph] , [451 ! 2,4- (Cl) ₂ -Ph, 2,6- (F) ₂ -Ph, 2-F-Ph] , [452 ! 2,4- (Cl) ₂ -Ph, 2,6- (F) ₂ -Ph, 2 -Cl -Ph] , [453 ! 2,4- (Cl) ₂ -Ph, 2,6- (F) ₂ -Ph, 3- CF ₃ -Ph] , [454 ! 2,4- (Cl) ₂ -Ph, 2,6- (F) ₂ -Ph, 4 -MeS-Ph] , [455 ! 2,4- (Cl) ₂ -Ph, 2,6- (F) ₂ -Ph, 4 -CN-Ph] , [456 ! 2,4- (Cl) ₂ -Ph, 2,6- (F) ₂ -Ph, 4 -AcNH- Ph] , [457 ! 2,4- (Cl) ₂ -Ph, 3,4- (F) ₂ -Ph, 2-F-Ph] , [458 ! 2,4- (Cl) ₂ -Ph, 3,4- (F) ₂ -Ph, 2-Cl-Ph] , [459 ! 2,4- (Cl) ₂ -Ph, 3,4- (F) ₂ -Ph, 3-CF ₃ -Ph] , [460 ! 2,4-(Cl) ₂ -Ph, 3,4- (F) ₂ -Ph, 4-MeS-Ph] , [461 ! 2,4- (Cl) ₂ -Ph, 3,4- (F) ₂ -Ph, 4- CN-Ph] , [462 ! 2,4- (Cl) ₂ -Ph, 3,4- (F) ₂ -Ph, 4 -AcNH-Ph] , [463 ! 2,4- (Cl) ₂ -Ph, 3,5-(F) ₂ -Ph, 2-F-PhJ , [464 ! 2,4-(Cl) ₂ -Ph, 3,5- (F) ₂ -Ph, 2-Cl-Ph] , [465 ! 2,4- (Cl) ₂ -Ph, 3,5- (F) ₂ -Ph, 3- CF ₃ -Ph] , [466 ! 2,4- (Cl) ₂ -Ph, 3,5- (F) ₂ -Ph, 4-MeS-Ph] , [467 ! 2,4- (Cl) ₂ -Ph, 3,5-(F) ₂ -Ph, 4 -CN- Ph] , [468 ! 2,4- (Cl) ₂ -Ph, 3,5- (F) ₂ -Ph, 4 -AcNH- Ph] , [469 ! 2,4- (Cl) ₂ -Ph, 4-Et-Ph, Ph] ,

[470 ! 2,4-(Cl) ₂ -Ph, 4-Et-Ph, 3-F-Ph] , [471 ! 2 , 4- (Cl) ₂ -Ph, 4-Et-Ph, 3-Me-Ph] , [472 ! 2,4- (Cl) ₂ -Ph, 4-Et-Ph, 4-F-Ph] ,

[473 ! 2,4- (Cl) ₂ -Ph, 4-Et-Ph, 4-Me-Ph] , [474 ! 2,4- (Cl) ₂ -Ph, 4-Et-Ph, 4-CF ₃ -Ph] , [475 ! 2,4- (Cl) ₂ -Ph, 4-Et-Ph, 4-Ph, Ph] ,

[476 ! 2,4- (Cl) ₂ -Ph, 4-Et-Ph, 3,4- (Me) ₂ -Ph] , [477 ! 2,4-

(Cl) ₂ -Ph, 4-Et-Ph, 5-In] , [478 ! 2,4- (Cl) ₂ -Ph, 4-EtS-Ph, Ph] , [479 ! 2,4- (Cl) ₂ -Ph ₇ 4-EtS-Ph, 3-F-Ph] , [480 ! 2,4-

(Cl) ₂ -Ph, 4-EtS-Ph, 3-Me-Ph] , [481 ! 2,4-(Cl) ₂ -Ph, 4-EtS-Ph, 4-F-Ph] , [482 ! 2,4-(Cl) ₂ -Ph, 4-EtS-Ph, 4-Me-Ph] , [483 ! 2,4-

(Cl) ₂ -Ph, 4-EtS-Ph, 4-CF ₃ -Ph] , [484 ! 2,4-(Cl) ₂ -Ph, 4-EtS- Ph, 4-Ph, Ph] , [485 ! 2,4-(Cl) ₂ -Ph, 4-EtS-Ph, 3,4-(Me) ₂ -Ph] ,

[486 ! 2,4-(Cl) ₂ -Ph, 4-EtS-Ph, 5-In] , [487 ! 2,4-(Cl) ₂ -Ph, 4- CN-Ph, Ph] , [488 ! 2,4-(Cl) ₂ -Ph, 4-CN-Ph, 3-F-Ph] , [489 ! 2,4- (Cl) ₂ -Ph, 4-CN-Ph, 3-Me-Ph] , [490 ! 2,4-(Cl) ₂ -Ph, 4-CN- Ph, 4-F-Ph] , [491 ! 2,4-(Cl) ₂ -Ph, 4-CN-Ph, 4-Me-Ph] , [492 ! 2,4- (Cl) ₂ -Ph, 4-CN-Ph, 4-CF ₃ -Ph] , [493 ! 2,4-(Cl) ₂ -Ph, 4-CN- Ph, 4-Ph, Ph] , [494.' 2,4-(Cl) ₂ -Ph, 4-CN-Ph, 3,4-(Me) ₂ -Ph] ,

[495 ! 2,4-(Cl) ₂ -Ph, 4-CN-Ph, 5-In] , [496 ! 2,4-(Cl) ₂ -Ph ₇ 4- AcNH-Ph, Ph] , [497 ! 2,4-(Cl) ₂ -Ph, 4-AcNH-Ph, 3-F-Ph] , [498

! 2,4-(Cl) ₂ -Ph, 4-AcNH-Ph, 3-Me-Ph] , [499 ! 2,4-(Cl) ₂ -Ph, 4- AcNH-Ph, 4-F-Ph] , [500 ! 2,4-(Cl) ₂ -Ph, 4-AcNH-Ph, 4-Me-Ph] ,

[501.' 2,4-(Cl) ₂ -Ph, 4-AcNH-Ph, 4-CF ₃ -Ph] , [502. ^' 2 , 4- (Cl) ₂ - Ph, 4-AcNH-Ph, 4-Ph, Ph] , [503 ! 2,4-(Cl) ₂ -Ph, 4-AcNH-Ph, 3,4-(Me) ₂ -Ph] , [504 ! 2,4-(Cl) ₂ -Ph, 4-AcNH-Ph, 5-In] , [505 ! 2,4- (Cl) ₂ -Ph, 5-In _λ Ph] , [506 ! 2,4-(Cl) ₂ -Ph, 5-In, 3-F-Ph] ,

[507 ! 2,4-(Cl) ₂ -Ph, 5-In, 3-Me-Ph] , [508. ^" 2,4-(Cl) ₂ -Ph, 5- In, 4-F-Ph] , [509 ! 2,4-(Cl) ₂ -Ph, 5-In, 4-Me-Ph] , [510 ! 2,4-

(Cl) ₂ -Ph, 5-In, 4-CF ₃ -Ph] , [511 ! 2,4-(Cl) ₂ -Ph, 5-In, 4-Ph, Ph] , [512 ! 2,4-(Cl) ₂ -Ph, 5-In, 3,4-(Me) ₂ -Ph] , [513 ! 2,4-

(Cl) ₂ -Ph, 5-In _^ 5-In] , [514 ! 2,4-(Cl) ₂ -Ph, 1-Np, Ph] , [515 ! 2,4- (Cl) ₂ -Ph, l-Np _λ 3-F-Ph] , [516 ! 2,4-(Cl) ₂ -Ph, 1-Np^ 3-Me- Ph] , [517 ! 2,4-(Cl) ₂ -Ph, 1-Np, 4-F-Ph] , [518 ! 2,4-(Cl) ₂ -Ph,

1-Np, 4-Me-Ph] , [519 ! 2 , 4- (Cl) ₂ -Ph, 1-Np, 4-CF ₃ -Ph] , [520 ! 2,4- (Cl) ₂ -Ph, 1-Np, 4-Ph, Ph] , [521 ! 2,4-(Cl) ₂ -Ph, 1-Np, 3,4-(Me) ₂ -Ph] , [522 ^' .2,4-(Cl) ₂ -Ph, 1-Np, 5-In] , [523 ! 2,4-

(Cl) ₂ -Ph, 3-Me-2-Np, Ph] , [524 ! 2,4-(Cl) ₂ -Ph, 3-Me-2-Np, 3- F-Ph] , [525 : 2,4- (Cl) ₂ -Ph, 3 -Me -2 -Np, 3 -Me-Ph] , [526 ! 2,4-

(Cl) ₂ -Ph, 3-Me-2-Np, 4-F-Ph] , [527 ! 2,4-(Cl) ₂ -Ph, 3-Me-2- Np, 4-Me-Ph] , [528 ^" .2,4-(Cl) ₂ -Ph, 3-Me-2-Np, 4-CF ₃ -Ph] ,

[529 ! 2,4-(Cl) ₂ -Ph, 3-Me-2-Np, 4-Ph, Ph] , [530 ! 2 , 4- (Cl) ₂ - Ph, 3-Me-2-Np, 3,4-(Me) ₂ -Ph] , [531 ! 2,4-(Cl) ₂ -Ph, 3-Me-2-Np , 5-In] , [532 ! 3,5-(Cl) ₂ -Ph, Ph, 2-Me-Ph] , [533 ! 3,5-(Cl) ₂ - Ph, 2-F-Ph, 2-F-Ph] , [534 ! 3,5-(Cl) ₂ -Ph, 2-F-Ph, 2-Cl-Ph] ,

[535 ! 3,5-(Cl) ₂ -Ph, 2-F-Ph, 3-CF ₃ -Ph] , [536 ! 3,5-(Cl) ₂ -Ph, 2-F-Ph, 4-MeS-Ph] , [537 ! 3,5-(Cl) ₂ -Ph, 2-F-Ph, 4-CN-Ph] ,

[538 ^' .3,5-(Cl) ₂ -Ph, 2-F-Ph, 4 -AcNH-Ph] , [539 ! 3,5-(Cl) ₂ -Ph, 3-Cl-Ph, 2-Me-Ph] , [540 ! 3,5-(Cl) ₂ -Ph, 3-Cl-Ph, 2-F-Ph] ,

[541 ! 3,5-(Cl) ₂ -Ph, 3-Cl-Ph, 2-Cl-Ph] , [542 ! 3,5-(Cl) ₂ -Ph ₇ 3-Cl-Ph, 3-CF ₃ -Ph] , [543 ! 3,5-(Cl) ₂ -Ph, 3-Cl-Ph, 4-MeS-Ph] ,

[544 ! 3,5-(Cl) ₂ -Ph, 3-Cl-Ph, 4-CN-Ph] , [545 ! 3,5-(Cl) ₂ -Ph, 3-Cl-Ph, 4 -AcNH- Ph] , [546 ! 3,5-(Cl) ₂ -Ph, 3-CF ₃ -Ph, 2-Me- Ph] , [547 ! 3,5-(Cl) ₂ -Ph, 4-F-Ph, 2-Me-Ph] , [548 ! 3,5-(Cl) ₂ - Ph, 4-F-Ph, 2-F-Ph] , [549 ^" .3,5-(Cl) ₂ -Ph, 4-F-Ph, 2-Cl-Ph] ,

[550 ! 3,5-(Cl) ₂ -Ph, 4-F-Ph, 3-CF ₃ -Ph] , [551 ! 3,5-(Cl) ₂ -Ph, 4-F-Ph, 4-MeS-Ph] , [552 ! 3,5-(Cl) ₂ -Ph, 4-F-Ph, 4-CN-Ph] ,

[553 ! 3,5-(Cl) ₂ -Ph, 4-F-Ph, 4 -AcNH-Ph] , [554 ! 3,5-(Cl) ₂ -Ph, 4-MeO-Ph, 2-Me-Ph] , [555 ! 3,5-(Cl) ₂ -Ph, 2,3-(Cl) ₂ -Ph, 2-Me-

Ph] , [556 ! 3,5- (Cl) ₂ -Ph, 2,3- (Cl) ₂ -Ph, 2-F-Ph] , [557 ! 3,5- (Cl) ₂ -Ph, 2,3- (Cl) ₂ -Ph, 2-Cl-Ph] , [558 ! 3,5- (Cl) ₂ -Ph, 2,3- (Cl) ₂ -Ph, 3-CF ₃ -Ph] , [559 ^" . 3,5- (Cl) ₂ -Ph, 2,3- (Cl) ₂ -Ph, 4- MeS-Ph] , [560 I 3,5- (Cl) ₂ -Ph, 2,3- (Cl) ₂ -Ph, 4-CN-Ph] , [5611 3,5- (Cl) ₂ -Ph, 2,3- (Cl) ₂ -Ph, 4 -AcNH- Ph] , [562 ! 3,5- (Cl) ₂ -Ph, 2,4- (F) ₂ -Ph, 2-F-Ph] , [563 ! 3,5- (Cl) ₂ -Ph, 2,4- (F) ₂ -Ph, 2- Cl-Ph] , [564 ! 3,5- (Cl) ₂ -Ph, 2,4- (F) ₂ -Ph, 3-CF ₃ -Ph] , [565 ! 3,5- (Cl) ₂ -Ph, 2,4- (F) ₂ -Ph, 4 -MeS-Ph] , [566 ! 3,5- (Cl) ₂ -Ph, 2,4- (F) ₂ -Ph, 4 -CN-Ph] , [567 ! 3,5- (Cl) ₂ -Ph, 2,4- (F) ₂ -Ph, 4- AcNH-Ph] , [568 ! 3,5- (Cl) ₂ -Ph, 2,6- (F) ₂ -Ph, 2-F-Ph] , [569 ! 3,5- (Cl) ₂ -Ph, 2,6- (F) ₂ -Ph, 2-Cl-Ph] , [570 ! 3,5- (Cl) ₂ -Ph, 2,6-(F) ₂ -Ph, 3-CF ₃ -Ph] , [571 ! 3,5- (Cl) ₂ -Ph, 2,6- (F) ₂ -Ph, 4- MeS-Ph] , [572 ! 3,5- (Cl) ₂ -Ph, 2,6- (F) ₂ -Ph, 4 -CN- Ph] , [573 ! 3,5- (Cl) ₂ -Ph, 2,6- (F) ₂ -Ph, 4 -AcNH- Ph] , [574 ^' .3,5- (Cl) ₂ -Ph, 3,4- (F) ₂ -Ph, 2-F-Ph] , [575 ! 3,5- (Cl) ₂ -Ph, 3,4- (F) ₂ -Ph, 2- Cl-Ph] , [576 ! 3,5- (Cl) ₂ -Ph, 3,4- (F) ₂ -Ph, 3-CF ₃ -Ph] , [577 ! 3,5- (Cl) ₂ -Ph, 3,4- (F) ₂ -Ph, 4 -MeS- Ph] , [578 ! 3,5- (Cl) ₂ -Ph, 3,4-(F) ₂ -Ph, 4 -CN-Ph] , [579 ! 3,5- (Cl) ₂ -Ph, 3,4- (F) ₂ -Ph, 4- AcNH-Ph] , [580 ! 3,5- (Cl) ₂ -Ph, 3,5- (F) ₂ -Ph, 2-F-Ph] , [581 ! 3,5- (Cl) ₂ -Ph, 3,5- (F) ₂ -Ph, 2-Cl-Ph] , [582 ! 3,5-(Cl) ₂ -Ph, 3,5- (F) ₂ -Ph, 3-CF ₃ -Ph] , [583 ! 3,5- (Cl) ₂ -Ph, 3,5- (F) ₂ -Ph, 4- MeS-Ph] , [584 ! 3,5- (Cl) ₂ -Ph, 3,5- (F) ₂ -Ph, 4 -CN-Ph] , [585 ! 3,5- (Cl) ₂ -Ph, 3,5- (F) ₂ -Ph, 4 -AcNH-Ph] , [586 ! 3,5- (Cl) ₂ -Ph, 4-Et-Ph, Ph] , [587 ! 3,5- (Cl) ₂ -Ph, 4-Et-Ph, 3-F-Ph] , [588 ! 3,5- (Cl) ₂ -Ph, 4-Et-Ph, 3-Me-Ph] , [589 ! 3,5- (Cl) ₂ -Ph, 4-Et-

Ph, 4 -F-Ph] , [590 : 3,5- (Cl) ₂ -Ph, 4-Et-Ph, 4-Me-Ph] , [591 ! 3,5- (Cl) ₂ -Ph, 4-Et-Ph, 4-CF ₃ -Ph] , [592 ! 3,5-(Cl) ₂ -Ph, 4-Et- Ph, 4-Ph, Ph] , [593 ^" .3,5-(Cl) ₂ -Ph, 4-Et-Ph, 3,4-(Me) ₂ -Ph] , [594 ! 3,5-(Cl) ₂ -Ph, 4-Et-Ph, 5-In] , [595 ! 3,5-(Cl) ₂ -Ph, 4- EtS-Ph, Ph] , [596 ! 3,5-(Cl) ₂ -Ph, 4-EtS-Ph, 3-F-Ph] , [597 ! 3,5- (Cl) ₂ -Ph, 4-EtS-Ph, 3-Me-Ph] , [598 ! 3 , 5- (Cl) ₂ -Ph, 4- EtS-Ph, 4-F-Ph] , [599 '.3,5-(Cl) ₂ -Ph, 4-EtS-Ph, 4-Me-Ph] , [600 ! 3,5-(Cl) ₂ -Ph, 4-EtS-Ph, 4-CF ₃ -Ph] , [601 ! 3 , 5- (Cl) ₂ - Ph, 4-EtS-Ph, 4-Ph, Ph] , [602 ! 3,5-(Cl) ₂ -Ph, 4-EtS-Ph, 3,4- (Me) ₂ -Ph] , [603 ^' .3,5-(Cl) ₂ -Ph, 4-EtS-Ph, 5-In] , [604 ! 3,5- (Cl) ₂ -Ph, 4-CN-Ph, Ph] , [605 ! 3,5-(Cl) ₂ -Ph, 4-CN-Ph, 3-F- Ph] , [606 ! 3,5-(Cl) ₂ -Ph, 4-CN-Ph, 3-Me-Ph] , [607 ! 3,5- (Cl) ₂ -Ph, 4-CN-Ph, 4-F-Ph] , [608 ! 3,5-(Cl) ₂ -Ph, 4-CN-Ph, 4- Me-Ph] , [609 ^' .3,5-(Cl) ₂ -Ph, 4-CN-Ph, 4-CF ₃ -Ph] , [610 ! 3,5- (Cl) ₂ -Ph, 4-CN-Ph, 4-Ph, Ph] , [611 ! 3,5-(Cl) ₂ -Ph, 4-CN-Ph, 3,4-(Me) ₂ -Ph] , [612 ! 3,5-(Cl) ₂ -Ph, 4-CN-Ph, 5-In] , [613 ! 3,5- (Cl) ₂ -Ph, 4-AcNH-Ph, Ph] , [614 ! 3,5-(Cl) ₂ -Ph, 4-AcNH- Ph, 3-F-Ph] , [615 ! 3,5-(Cl) ₂ -Ph, 4-AcNH-Ph, 3-Me-Ph] , [616 ! 3,5-(Cl) ₂ -Ph, 4-AcNH-Ph, 4-F-Ph] , [617 ! 3,5-(Cl) ₂ -Ph, 4- AcNH-Ph, 4-Me-Ph] , [618 ! 3,5-(Cl) ₂ -Ph, 4-AcNH-Ph, 4-CF ₃ - Ph] , [619 ^' .3,5-(Cl) ₂ -Ph, 4-AcNH-Ph, 4-Ph, Ph] , [620 ^' .3,5- (Cl) ₂ -Ph, 4-AcNH-Ph, 3,4-(Me) ₂ -Ph] , [621 ! 3,5-(Cl) ₂ -Ph, 4- AcNH-Ph, 5-In] , [622 ! 3,5-(Cl) ₂ -Ph, 5-In _> Ph] , [623 ! 3,5- (Cl) ₂ -Ph, 5-In, 3-F-Ph] , [624 ! 3,5-(Cl) ₂ -Ph, 5-In, 3-Me- Ph] , [625 ! 3,5-(Cl) ₂ -Ph, 5-In, 4-F-Ph] , [626 ^' .3,5-(Cl) ₂ -Ph,

5-In ₇ 4-Me-Ph] , [627 ! 3,5-(Cl) ₂ -Ph, 5-In, 4-CF ₃ -Ph] , [628 ! 3,5- (Cl) ₂ -Ph, 5 -In, 4-Ph, Ph] , [629 ! 3,5-(Cl) ₂ -Ph, 5-In, 3,4-(Me) ₂ -Ph] , [630 ! 3,5-(Cl) ₂ -Ph, 5-In, 5-In] , [63l ! 3,5- (Cl) ₂ -Ph, 1-Np, Ph] , [632 ! 3,5-(Cl) ₂ -Ph, 1-Np,, 3-F-Ph] , [633 ! 3,5-(Cl) ₂ -Ph, 1-Np, 3-Me-Ph] , [634 ! 3,5-(Cl) ₂ -Ph, 1- Np, 4-F-Ph] , [635 ! 3,5-(Cl) ₂ -Ph, 1-Np, 4-Me-Ph] , [636 ! 3,5- (Cl) ₂ -Ph, 1-Np, 4-CF ₃ -Ph] , [637 ! 3,5-(Cl) ₂ -Ph, 1-Np, 4-Ph, Ph] , [638 ! 3,5-(Cl) ₂ -Ph, 1-Np, 3,4- (Me) ₂ -Ph] , [639 ! 3,5- (Cl) ₂ -Ph, 1-Np, 5-In] , [640 ! 3,5-(Cl) ₂ -Ph, 3-Me-2-Np, Ph] , [641 ^' .3,5-(Cl) ₂ -Ph, 3-Me-2-Np, 3-F-Ph] , [642 ! 3,5-(Cl) ₂ -Ph, 3-Me-2-Np, 3-Me-Ph] , [643 ! 3,5-(Cl) ₂ -Ph, 3-Me-2-Np, 4-F- Ph] , [644 ! 3,5-(Cl) ₂ -Ph, 3-Me-2-Np, 4-Me-Ph] , [645 ! 3,5- (Cl) ₂ -Ph, 3-Me-2-Np, 4-CF ₃ -Ph] , [646 ! 3,5-(Cl) ₂ -Ph, 3-Me-2- Np, 4-Ph, Ph] , [647 ^' .3,5-(Cl) ₂ -Ph, 3 -Me -2 -Np, 3,4- (Me) ₂ - Ph] , [648. ^' 3,5-(Cl) ₂ -Ph, 3-Me-2-Np, 5-In] , [649 ! 4-Et-Ph, Ph , Ph] , [650 ! 4-Et-Ph, 2-F-Ph, 2-Me-Ph] , [651 ! 4-Et-Ph, 2-F- Ph, 3-F-Ph] , [652 ! 4-Et-Ph, 2-F-Ph, 3-Me-Ph] , [653 ! 4-Et- Ph, 2-F-Ph, 4-F-Ph] , [654 ! 4-Et-Ph, 2-F-Ph, 4-Cl-Ph] , [655 ! 4-Et-Ph, 2-F-Ph, 4-Br-Ph] , [656 ! 4-Et-Ph, 2-F-Ph, 4-Me- Ph] , [657 ! 4-Et-Ph, 2-F-Ph, 4-iPr-Ph] , [658 ! 4-Et-Ph, 2-F- Ph, 4-CF ₃ -Ph] , [659 ! 4-Et-Ph, 2-F-Ph, 4 -MeO-Ph] , [660 ! 4- Et-Ph, 2-F-Ph, 4-Ph, Ph] , [661 ^' .4-Et-Ph, 2-F-Ph, 3,4- (Me) ₂ - Ph] , [662. ^' 4-Et-Ph, 2-F-Ph, 5-In] , [663. ^' 4-Et-Ph, 3-CF ₃ -Ph, 2-Me-Ph] , [664 ! 4-Et-Ph, 3-CF ₃ -Ph, 3-F-Ph] , [665 ! 4-Et-Ph, 3-CF ₃ -Ph, 3-Me-Ph] , [666 ! 4-Et-Ph, 3-CF ₃ -Ph, 4-F-Ph] , [667

; 4-Et-Ph, 3-CF ₃ -Ph, 4-Cl-Ph] , [668 ! 4-Et-Ph, 3-CF ₃ -Ph, 4- Br-Ph] , [669 ! 4-Et-Ph, 3-CF ₃ -Ph, 4-Me-Ph] , [670 ! 4-Et-Ph, 3-CF ₃ -Ph, 4-iPr-Ph] , [671 ! 4-Et-Ph, 3-CF ₃ -Ph, 4-CF ₃ -Ph] ,

[672 ! 4-Et-Ph, 3-CF ₃ -Ph, 4-MeO-Ph] , [673 ! 4-Et-Ph, 3-CF ₃ - Ph, 4-Ph, Ph] , [674 ! 4-Et-Ph, 3-CF ₃ -Ph, 3,4-(Me) ₂ -Ph] , [675

! 4-Et-Ph, 3-CF ₃ -Ph, 5-In] , [676 ! 4-Et-Ph, 4-F-Ph, 2-Me- Ph] , [677 ! 4-Et-Ph, 4-F-Ph, 3-F-Ph] , [678 ! 4-Et-Ph, 4-F-Ph, 3-Me-Ph] , [679 ! 4-Et-Ph, 4-F-Ph, 4-F-Ph] , [680 ! 4-Et-Ph, 4- F-Ph, 4 -Cl -Ph] , [681 ! 4-Et-Ph, 4-F-Ph, 4-Br-Ph] , [682 ! 4- Et-Ph, 4-F-Ph, 4-Me-Ph] , [683 ! 4-Et-Ph, 4-F-Ph, 4-iPr-Ph] ,

[684 ! 4-Et-Ph, 4-F-Ph, 4-CF ₃ -Ph] , [685 ! 4-Et-Ph, 4-F-Ph, 4- MeO-Ph] , [686 ! 4-Et-Ph, 4-F-Ph, 4-Ph, Ph] , [687 ! 4-Et-Ph, 4-F-Ph, 3,4-(Me) ₂ -Ph] , [688 ! 4-Et-Ph, 4-F-Ph, 5-In] , [689 ! 4-Et-Ph, 4-iPr-Ph, 2-Me-Ph] , [690 ! 4-Et-Ph, 4-iPr-Ph, 3-F- Ph] , [691 ! 4-Et-Ph, 4-iPr-Ph, 3-Me-Ph] , [692 ! 4-Et-Ph, 4- iPr-Ph, 4-F-Ph] , [693 ! 4-Et-Ph, 4-iPr-Ph, 4-Cl-Ph] , [694 ! 4-Et-Ph, 4-iPr-Ph, 4-Br-Ph] , [695 ! 4-Et-Ph, 4-iPr-Ph, 4-Me- Ph] , [696 ! 4-Et-Ph, 4-iPr-Ph, 4-iPr-Ph] , [697 ! 4-Et-Ph, 4- iPr-Ph, 4-CF ₃ -Ph] , [698 ! 4-Et-Ph, 4-iPr-Ph, 4-MeO-Ph] , [699

! 4-Et-Ph, 4-iPr-Ph, 4-Ph, Ph] , [700 ! 4-Et-Ph, 4-iPr-Ph, 3,4- (Me) ₂ -Ph],

[701 ! 4-Et-Ph, 4-iPr-Ph, 5-In] , [702 ! 4-Et-Ph, 4-CF ₃ -Ph, 2- Me-Ph] , [703 ! 4-Et-Ph, 4-CF ₃ -Ph, 3-F-Ph] , [704 ! 4-Et-Ph, 4- CF ₃ -Ph, 3-Me-Ph] , [705 ! 4-Et-Ph, 4-CF ₃ -Ph, 4-F-Ph] , [706 ! 4-Et-Ph, 4-CF ₃ -Ph, 4-Cl-Ph] , [707 ! 4-Et-Ph, 4-CF ₃ -Ph, 4-Br-

Ph] , [708 ! 4-Et-Ph, 4-CF ₃ -Ph, 4-Me-Ph] , [709 ! 4-Et-Ph, 4- CF ₃ -Ph, 4-iPr-Ph] , [710 ! 4-Et-Ph, 4-CF ₃ -Ph, 4-CF ₃ -Ph] , [711

! 4-Et-Ph, 4-CF ₃ -Ph, 4 -MeO- Ph] , [712 ! 4-Et-Ph, 4-CF ₃ -Ph, 4- Ph, Ph] , [713 ! 4-Et-Ph, 4-CF ₃ -Ph, 3,4-(Me) ₂ -Ph] , [714 ! 4- Et-Ph, 4-CF ₃ -Ph, 5-In] , [715 ! 4-Et-Ph, 4-Ph, Ph, 2-Me-Ph] ,

[716 ! 4-Et-Ph, 4-Ph, Ph, 3-F-Ph] , [717 ! 4-Et-Ph, 4-Ph, Ph, 3-Me-Ph] , [718 ! 4-Et-Ph, 4-Ph, Ph, 4-F-Ph] , [719 ! 4-Et-Ph, 4-Ph, Ph, 4-Cl-Ph] , [720 ! 4-Et-Ph, 4-Ph, Ph, 4-Br-Ph] , [721

! 4-Et-Ph, 4-Ph, Ph, 4-Me-Ph] , [722 ! 4-Et-Ph, 4-Ph, Ph, 4- iPr-Ph] , [723 ! 4-Et-Ph, 4-Ph, Ph, 4-CF ₃ -Ph] , [724 ! 4-Et-Ph, 4-Ph, Ph, 4-MeO-Ph] , [725 ! 4-Et-Ph, 4-Ph, Ph, 4-Ph, Ph] ,

[726 ! 4-Et-Ph, 4-Ph, Ph, 3,4-(Me) ₂ -Ph] , [727 ! 4-Et-Ph, 4- Ph, Ph, 5-In] , [728 ! 4-Et-Ph, 2,4-(F) ₂ -Ph, 2-Me-Ph] , [729 ! 4-Et-Ph, 2,4-(F) ₂ -Ph, 3-F-Ph] , [730 ! 4-Et-Ph, 2,4-(F) ₂ -Ph, 3-Me-Ph] , [731 ! 4-Et-Ph, 2,4-(F) ₂ -Ph, 4-F-Ph] , [732 ! 4-Et- Ph, 2,4-(F) ₂ -Ph, 4-Cl-Ph] , [733 ! 4-Et-Ph, 2,4-(F) ₂ -Ph, 4- Br-Ph] , [734 ! 4-Et-Ph, 2,4-(F) ₂ -Ph, 4-Me-Ph] , [735 ! 4-Et- Ph, 2,4-(F) ₂ -Ph, 4-iPr-Ph] , [736 ! 4-Et-Ph, 2,4-(F) ₂ -Ph, 4- CF ₃ -Ph] , [737 ! 4-Et-Ph, 2,4-(F) ₂ -Ph, 4-MeO-Ph] , [738 ! 4-Et- Ph, 2,4-(F) ₂ -Ph, 4-Ph, Ph] , [739 ! 4-Et-Ph, 2,4-(F) ₂ -Ph, 3,4-(Me) ₂ -Ph] , [740 ! 4-Et-Ph, 2,4-(F) ₂ -Ph, 5-In] , [741.4- Et-Ph, 3,4- (Cl) ₂ -Ph, 2-Me-Ph] , [742 ! 4-Et-Ph, 3,4-(Cl) ₂ -Ph, 3-F-Ph] , [743 ! 4-Et-Ph, 3,4-(Cl) ₂ -Ph, 3-Me-Ph] , [744 ! 4-Et- Ph, 3,4- (Cl) ₂ -Ph, 4-F-Ph] , [745 ! 4-Et-Ph, 3,4-(Cl) ₂ -Ph, 4- Cl-Ph] , [746 ! 4-Et-Ph, 3,4-(Cl) ₂ -Ph, 4-Br-Ph] , [747 ! 4-Et-

Ph, 3,4- (Cl) ₂ -Ph, 4-Me-Ph] , [748 ! 4-Et-Ph, 3,4-(Cl) ₂ -Ph, 4- iPr-Ph] , [749 : 4-Et-Ph, 3,4-(Cl) ₂ -Ph, 4-CF ₃ -Ph] , [750 ! 4- Et-Ph, 3,4- (Cl) ₂ -Ph, 4 -MeO-Ph] , [751 ! 4-Et-Ph, 3, 4-(Cl) ₂ - Ph, 4-Ph, Ph] , [752 ! 4-Et-Ph, 3,4-(Cl) ₂ -Ph, 3,4-(Me) ₂ -Ph] , [753 ! 4-Et-Ph, 3,4- (Cl) ₂ -Ph, 5-In] , [754 ! 4-Et-Ph, 3,5- (Cl) ₂ -Ph, 2-Me-Ph] , [755 ! 4-Et-Ph, 3,5-(Cl) ₂ -Ph, 3-F-Ph] , [756 ! 4-Et-Ph, 3,5- (Cl) ₂ -Ph, 3-Me-Ph] , [757 ! 4-Et-Ph, 3,5- (Cl) ₂ -Ph, 4-F-Ph] , [758 ! 4-Et-Ph, 3,5-(Cl) ₂ -Ph, 4-Cl-Ph] , [759 ! 4-Et-Ph, 3,5-(Cl) ₂ -Ph, 4-Br-Ph] , [760 ! 4-Et-Ph, 3,5- (Cl) ₂ -Ph, 4-Me-Ph] , [761 ! 4-Et-Ph, 3,5-(Cl) ₂ -Ph, 4-iPr-Ph] , [762 ! 4-Et-Ph, 3,5- (Cl) ₂ -Ph, 4-CF ₃ -Ph] , [763 ! 4-Et-Ph, 3,5- (Cl) ₂ -Ph, 4 -MeO-Ph] , [764 ! 4-Et-Ph, 3,5-(Cl) ₂ -Ph, 4-Ph, Ph] , [765 ! 4-Et-Ph, 3,5-(Cl) ₂ -Ph, 3,4-(Me) ₂ -Ph] , [766 ! 4- Et-Ph, 3,5- (Cl) ₂ -Ph, 5-In] , [767 ! 4-EtO-Ph, Ph _^ Ph] , [768 ! 4-EtO-Ph, 2-F-Ph, 2-Me-Ph] , [769 ! 4-EtO-Ph, 2-F-Ph, 3-F- Ph] , [770 ! 4-EtO-Ph, 2-F-Ph, 3-Me-Ph] , [771 ! 4-EtO-Ph, 2-F- Ph, 4-F-Ph] , [772 ! 4-EtO-Ph, 2-F-Ph, 4-Cl-Ph] , [773 ! 4-EtO- Ph, 2-F-Ph, 4-Br-Ph] , [774 ! 4-EtO-Ph, 2-F-Ph, 4-Me-Ph] , [775 ! 4-EtO-Ph, 2-F-Ph, 4-iPr-Ph] , [776 ! 4-EtO-Ph, 2-F-Ph, 4-CF ₃ -Ph] , [777 ! 4-EtO-Ph, 2-F-Ph, 4-MeO-Ph] , [778 ! 4-EtO- Ph, 2-F-Ph, 4-Ph, Ph] , [779 ! 4-EtO-Ph, 2-F-Ph, 3,4- (Me) ₂ - Ph] , [780 ! 4-EtO-Ph, 2-F-Ph, 5-In] , [781 ! 4-EtO-Ph, 3-CF ₃ - Ph, 2-Me-Ph] , [782 ! 4-EtO-Ph, 3-CF ₃ -Ph, 3 -F-Ph] , [783 ! 4- EtO-Ph, 3-CF ₃ -Ph, 3-Me-Ph] , [784 ! 4-EtO-Ph, 3-CF ₃ -Ph, 4-F- Ph] , [785 ! 4-EtO-Ph, 3-CF ₃ -Ph, 4-Cl-Ph] , [786 ! 4-EtO-Ph, 3-

CF ₃ -Ph, 4-Br-Ph] , [787 ! 4-EtO-Ph, 3-CF ₃ -Ph, 4-Me-Ph] , [788

14-EtO-Ph, 3-CF ₃ -Ph, 4-iPr-Ph] , [789 ! 4-EtO-Ph, 3-CF ₃ -Ph, 4-CF ₃ -Ph] , [790 ! 4-EtO-Ph, 3-CF ₃ -Ph, 4 -MeO- Ph] , [791 ! 4- EtO-Ph, 3-CF ₃ -Ph, 4-Ph, Ph] , [792 ! 4-EtO-Ph, 3-CF ₃ -Ph, 3,4-

(Me) ₂ -Ph] , [793 ! 4-EtO-Ph, 3-CF ₃ -Ph, 5-In] , [794 ! 4-EtO-Ph, 4-F-Ph, 2-Me-Ph] , [795 ! 4-EtO-Ph, 4-F-Ph, 3-F-Ph] , [796 ! 4- EtO-Ph, 4-F-Ph, 3-Me-Ph] , [797 ! 4-EtO-Ph, 4-F-Ph, 4-F-Ph] ,

[798 ! 4-EtO-Ph, 4-F-Ph, 4-Cl-Ph] , [799 ! 4-EtO-Ph, 4-F-Ph, 4-Br-Ph] , [800 ! 4-EtO-Ph, 4-F-Ph, 4-Me-Ph] , [801 ! 4-EtO-Ph, 4-F-Ph, 4-iPr-Ph] , [802 ! 4-EtO-Ph, 4-F-Ph, 4-CF ₃ -Ph] , [803

! 4-EtO-Ph, 4-F-Ph, 4-MeO-Ph] , [804 ! 4-EtO-Ph, 4-F-Ph, 4- Ph, Ph] , [805 ! 4-EtO-Ph, 4-F-Ph, 3,4-(Me) ₂ -Ph] , [806 ! 4- EtO-Ph, 4-F-Ph, 5-In] , [807 ! 4-EtO-Ph, 4-iPr-Ph, 2-Me-Ph] ,

[808 ! 4-EtO-Ph, 4-iPr-Ph, 3-F-Ph] , [809 ! 4-EtO-Ph, 4-iPr- Ph, 3-Me-Ph] , [810 ! 4-EtO-Ph, 4-iPr-Ph, 4-F-Ph] , [811 ! 4- EtO-Ph, 4-iPr-Ph, 4-Cl-Ph] , [812 ! 4-EtO-Ph, 4-iPr-Ph, 4-Br- Ph] , [813 ! 4-EtO-Ph, 4-iPr-Ph, 4-Me-Ph] , [814 ! 4-EtO-Ph, 4- iPr-Ph, 4-iPr-Ph] , [815 ! 4-EtO-Ph, 4-iPr-Ph, 4-CF ₃ -Ph] ,

[816 ! 4-EtO-Ph, 4-iPr-Ph, 4-MeO-Ph] , [817 ! 4-EtO-Ph, 4-iPr- Ph, 4-Ph, Ph] , [818 ! 4-EtO-Ph, 4-iPr-Ph, 3,4-(Me) ₂ -Ph] ,

[819 ! 4-EtO-Ph, 4-iPr-Ph, 5-In] , [820 ! 4-EtO-Ph, 4-CF ₃ -Ph, 2-Me-Ph] , [821 ! 4-EtO-Ph, 4-CF ₃ -Ph, 3-F-Ph] , [822 ! 4-EtO- Ph, 4-CF ₃ -Ph, 3-Me-Ph] , [823 ! 4-EtO-Ph, 4-CF ₃ -Ph, 4-F-Ph] ,

[824 ! 4-EtO-Ph, 4-CF ₃ -Ph, 4-Cl-Ph] , [825 ! 4-EtO-Ph, 4-CF ₃ - Ph, 4-Br-Ph] , [826 ! 4-EtO-Ph, 4-CF ₃ -Ph, 4-Me-Ph] , [827 ! 4-

EtO-Ph, 4-CF ₃ -Ph, 4-iPr-Ph] , [828 ! 4-EtO-Ph, 4-CF ₃ -Ph, 4- CF ₃ -Ph] , [829 ! 4-EtO-Ph, 4-CF ₃ -Ph, 4-MeO-Ph] , [830 ! 4-EtO- Ph, 4-CF ₃ -Ph, 4-Ph, Ph] , [831. ^' 4-EtO-Ph, 4-CF ₃ -Ph, 3,4- (Me) ₂ -Ph] , [832 ! 4-EtO-Ph, 4-CF ₃ -Ph, 5-In] , [833 ! 4-EtO-Ph, 4-Ph, Ph, 2-Me-Ph] , [834 ! 4-EtO-Ph, 4-Ph, Ph, 3-F-Ph] , [835 ! 4-EtO-Ph, 4-Ph, Ph, 3-Me-Ph] , [836 ! 4-EtO-Ph, 4-Ph, Ph, 4-F-Ph] , [837 ! 4-EtO-Ph, 4-Ph, Ph, 4-Cl-Ph] , [838 ! 4-EtO- Ph, 4-Ph, Ph, 4-Br-Ph] , [839 ! 4-EtO-Ph, 4-Ph, Ph, 4-Me-Ph] , [840 ! 4-EtO-Ph, 4-Ph, Ph, 4-iPr-Ph] , [841 ! 4-EtO-Ph, 4-Ph, Ph, 4-CF ₃ -Ph] , [842 ! 4-EtO-Ph, 4-Ph, Ph, 4-MeO-Ph] , [843 ! 4-EtO-Ph, 4-Ph, Ph, 4-Ph, Ph] , [844 ! 4-EtO-Ph, 4-Ph, Ph, 3,4-(Me) ₂ -Ph] , [845 ! 4-EtO-Ph, 4-Ph, Ph, 5-In] , [846 ! 4- EtO-Ph, 2,4-(F) ₂ -Ph, 2-Me-Ph] , [847 ! 4-EtO-Ph, 2,4-(F) ₂ -Ph, 3-F-Ph] , [848 ! 4-EtO-Ph, 2,4-(F) ₂ -Ph, 3-Me-Ph] , [849 ! 4- EtO-Ph, 2,4-(F) ₂ -Ph, 4-F-Ph] , [850.' 4-EtO-Ph, 2,4-(F) ₂ -Ph, 4-Cl-Ph] , [851 ! 4-EtO-Ph, 2,4-(F) ₂ -Ph, 4-Br-Ph] , [852 ! 4- EtO-Ph, 2,4-(F) ₂ -Ph, 4-Me-Ph] , [853 ! 4-EtO-Ph, 2,4-(F) ₂ -Ph, 4-iPr-Ph] , [854 ! 4-EtO-Ph, 2,4-(F) ₂ -Ph, 4-CF ₃ -Ph] , [855 ! 4- EtO-Ph, 2,4-(F) ₂ -Ph, 4-MeO-Ph] , [856 ! 4-EtO-Ph, 2,4- (F) ₂ - Ph, 4-Ph, Ph] , [857 ! 4-EtO-Ph, 2,4-(F) ₂ -Ph, 3,4-(Me) ₂ -Ph] , [858 ! 4-EtO-Ph, 2,4-(F) ₂ -Ph, 5-In] , [859 ! 4-EtO-Ph, 3,4- (Cl) ₂ -Ph, 2-Me-Ph] , [860 ! 4-EtO-Ph, 3,4-(Cl) ₂ -Ph, 3-F-Ph] , [861 ! 4-EtO-Ph, 3,4-(Cl) ₂ -Ph, 3-Me-Ph] , [862 ! 4-EtO-Ph, 3,4- (Cl) ₂ -Ph, 4-F-Ph] , [863 ! 4-EtO-Ph, 3,4-(Cl) ₂ -Ph, 4-C1- Ph] , [864 ! 4-EtO-Ph, 3,4-(Cl) ₂ -Ph, 4-Br-Ph] , [865 ! 4-EtO-

Ph, 3,4- (Cl) ₂ -Ph, 4-Me-Ph] , [866 ! 4-EtO-Ph, 3,4- (Cl) ₂ -Ph, 4-iPr-Ph] , [867 ! 4-EtO-Ph, 3,4- (Cl) ₂ -Ph, 4-CF ₃ -Ph] , [868 ! 4-EtO-Ph, 3,4- (Cl) ₂ -Ph, 4 -MeO- Ph] , [869 ! 4-EtO-Ph, 3,4- (Cl) ₂ -Ph, 4-Ph, Ph] , [870 ! 4-EtO-Ph, 3,4- (Cl) ₂ -Ph, 3,4- (Me) ₂ -Ph] , [871 ! 4-EtO-Ph, 3,4- (Cl) ₂ -Ph, 5-In] , [872 ! 4- EtO-Ph ₇ 3,5- (Cl) ₂ -Ph, 2-Me-Ph] , [873 ! 4-EtO-Ph, 3, 5- (Cl) ₂ - Ph, 3-F-Ph] , [874 ! 4-EtO-Ph, 3,5- (Cl) ₂ -Ph, 3-Me-Ph] , [875 ! 4-EtO-Ph, 3,5- (Cl) ₂ -Ph, 4-F-Ph] , [876 ! 4-EtO-Ph, 3, 5- (Cl) ₂ - Ph, 4-Cl-Ph] , [877 ! 4-EtO-Ph, 3,5-(Cl) ₂ -Ph, 4-Br-Ph] , [878 ! 4-EtO-Ph, 3,5- (Cl) ₂ -Ph, 4-Me-Ph] , [879 ! 4-EtO-Ph, 3,5- (Cl) ₂ -Ph, 4-iPr-Ph] , [880 ! 4-EtO-Ph, 3,5-(Cl) ₂ -Ph, 4-CF ₃ - Ph] , [881 ! 4-EtO-Ph, 3,5-(Cl) ₂ -Ph, 4-MeO-Ph] , [882 ! 4-EtO- Ph, 3,5- (Cl) ₂ -Ph, 4-Ph, Ph] , [883 ! 4-EtO-Ph, 3,5-(Cl) ₂ -Ph, 3,4-(Me) ₂ -Ph] , [884 ! 4-EtO-Ph, 3,5-(Cl) ₂ -Ph, 5-In] , [885 ! 4-MeS-Ph, Ph. Ph] , [886 ! 4-MeS-Ph, 2-F-Ph, 2-Me-Ph] , [887 ! 4-MeS-Ph, 2-F-Ph, 3-F-Ph] , [888 ! 4-MeS-Ph, 2-F-Ph, 3-Me- Ph] , [889 ! 4-MeS-Ph, 2-F-Ph, 4-F-Ph] , [890 ! 4-MeS-Ph, 2-F- Ph, 4-Cl-Ph] , [891 ! 4-MeS-Ph, 2-F-Ph, 4-Br-Ph] , [892 ! 4- MeS-Ph, 2-F-Ph, 4-Me-Ph] , [893 ! 4-MeS-Ph, 2-F-Ph, 4-iPr- Ph] , [894 ! 4-MeS-Ph, 2-F-Ph, 4-CF ₃ -Ph] , [895 ! 4-MeS-Ph, 2- F-Ph, 4-MeO-Ph] , [896 ! 4-MeS-Ph, 2-F-Ph, 4-Ph, Ph] , [897 ! 4-MeS-Ph, 2-F-Ph, 3,4-(Me) ₂ -Ph] , [898 ! 4-MeS-Ph, 2-F-Ph, 5- In] , [899 ! 4-MeS-Ph, 3-CF ₃ -Ph, 2-Me-Ph] , [900 ! 4-MeS-Ph, 3- CF ₃ -Ph, 3-F-Ph]. [901 ! 4-MeS-Ph, 3-CF ₃ -Ph, 3-Me-Ph] , [902 ! 4-MeS-Ph, 3-CF ₃ -

Ph, 4-F-Ph] , [903 ! 4-MeS-Ph, 3-CF ₃ -Ph, 4-Cl-Ph] , [904 ! 4- MeS-Ph, 3-CF ₃ -Ph, 4-Br-Ph] , [905 ! 4-MeS-Ph, 3-CF ₃ -Ph, 4-Me- Ph] , [906 ! 4-MeS-Ph, 3-CF ₃ -Ph, 4-iPr-Ph] , [907 ! 4-MeS-Ph, 3-CF ₃ -Ph, 4-CF ₃ -Ph] , [908 ! 4-MeS-Ph, 3-CF ₃ -Ph, 4-MeO-Ph] , [909 ! 4-MeS-Ph, 3-CF ₃ -Ph, 4-Ph, Ph] , [910 ! 4-MeS-Ph, 3-CF ₃ - Ph, 3,4-(Me) ₂ -Ph] , [911 ! 4-MeS-Ph, 3-CF ₃ -Ph, 5-In] , [912 ! 4-MeS-Ph, 4-F-Ph, 2-Me-Ph] , [913 ! 4-MeS-Ph, 4-F-Ph, 3-F- Ph] , [914 ! 4-MeS-Ph, 4-F-Ph, 3-Me-Ph] , [915 ! 4-MeS-Ph, 4-F- Ph, 4-F-Ph] , [916 ! 4-MeS-Ph, 4-F-Ph, 4-Cl-Ph] , [917 ! 4-MeS- Ph, 4-F-Ph, 4-Br-Ph] , [918 ! 4-MeS-Ph, 4-F-Ph, 4-Me-Ph] , [919 ! 4-MeS-Ph, 4-F-Ph, 4-iPr-Ph] , [920 ! 4-MeS-Ph, 4-F-Ph, 4-CF ₃ -Ph] , [921 ! 4-MeS-Ph, 4-F-Ph, 4-MeO-Ph] , [922 ! 4-MeS- Ph, 4-F-Ph, 4-Ph, Ph] , [923 ! 4-MeS-Ph, 4-F-Ph, 3,4- (Me) ₂ - Ph] , [924 ! 4-MeS-Ph, 4-F-Ph, 5-In] , [925 ! 4-MeS-Ph, 4-iPr- Ph, 2-Me-Ph] , [926 ! 4-MeS-Ph, 4-iPr-Ph, 3-F-Ph] , [927 ! 4- MeS-Ph, 4-iPr-Ph, 3-Me-Ph] , [928 ! 4-MeS-Ph, 4-iPr-Ph, 4-F- Ph] , [929 ! 4-MeS-Ph, 4-iPr-Ph, 4-Cl-Ph] , [930 ! 4-MeS-Ph, 4- iPr-Ph, 4-Br-Ph] , [931 ! 4-MeS-Ph, 4-iPr-Ph, 4-Me-Ph] , [932 ! 4-MeS-Ph, 4-iPr-Ph, 4-iPr-Ph] , [933 ! 4-MeS-Ph, 4-iPr-Ph, 4-CF ₃ -Ph] , [934 ! 4-MeS-Ph, 4-iPr-Ph, 4 -MeO- Ph] , [935 ! 4- MeS-Ph, 4-iPr-Ph, 4-Ph, Ph] , [936 ! 4-MeS-Ph, 4-iPr-Ph, 3,4- (Me) ₂ -Ph] , [937 ! 4-MeS-Ph, 4-iPr-Ph, 5-In] , [938 ! 4-MeS-Ph, 4-CF ₃ -Ph, 2-Me-Ph] , [939 ! 4-MeS-Ph, 4-CF ₃ -Ph, 3-F-Ph] , [940 ! 4-MeS-Ph, 4-CF ₃ -Ph, 3-Me-Ph] , [941 ! 4-MeS-Ph, 4-CF ₃ -Ph, 4-F-Ph] , [942 ! 4-MeS-Ph, 4-CF ₃ -Ph, 4-Cl-Ph] , [943 ! 4-MeS-

Ph, 4-CF ₃ -Ph, 4-Br-Ph] , [944 ! 4-MeS-Ph, 4-CF ₃ -Ph, 4-Me-Ph] , [945 ! 4-MeS-Ph, 4-CF ₃ -Ph, 4-iPr-Ph] , [946 ! 4-MeS-Ph, 4-CF ₃ - Ph, 4-CF ₃ -Ph] , [947 ! 4-MeS-Ph, 4-CF ₃ -Ph, 4-MeO-Ph] , [948 ! 4-MeS-Ph, 4-CF ₃ -Ph, 4-Ph, Ph] , [949 ! 4-MeS-Ph, 4-CF ₃ -Ph, 3,4-(Me) ₂ -Ph] , [950 ! 4-MeS-Ph, 4-CF ₃ -Ph, 5-In] , [951.4- MeS-Ph, 4-Ph, Ph, 2-Me-Ph] , [952 ! 4-MeS-Ph, 4-Ph, Ph, 3-F- Ph] , [953 ! 4-MeS-Ph, 4-Ph, Ph, 3-Me-Ph] , [954 ! 4-MeS-Ph, 4- Ph, Ph, 4-F-Ph] , [955 ! 4-MeS-Ph, 4-Ph, Ph, 4-Cl-Ph] , [956 ! 4-MeS-Ph, 4-Ph, Ph, 4-Br-Ph] , [957 ! 4-MeS-Ph, 4-Ph, Ph, 4- Me-Ph] , [958 ! 4-MeS-Ph, 4-Ph, Ph, 4-iPr-Ph] , [959 ! 4-MeS- Ph, 4-Ph, Ph, 4-CF ₃ -Ph] , [960 ! 4-MeS-Ph, 4-Ph, Ph, 4-MeO- Ph] , [961 ! 4-MeS-Ph, 4-Ph, Ph, 4-Ph, Ph] , [962 ! 4-MeS-Ph, 4-Ph, Ph, 3,4-(Me) ₂ -Ph] , [963 ! 4-MeS-Ph, 4-Ph, Ph, 5-In] , [964 ! 4-MeS-Ph, 2,4-(F) ₂ -Ph, 2-Me-Ph] , [965 ! 4-MeS-Ph, 2,4- (F) ₂ -Ph, 3-F-Ph] , [966 ! 4-MeS-Ph, 2,4-(F) ₂ -Ph, 3-Me-Ph] , [967 ! 4-MeS-Ph, 2,4-(F) ₂ -Ph, 4-F-Ph] , [968 ! 4-MeS-Ph, 2,4- (F) ₂ -Ph, 4-Cl-Ph] , [969 ! 4-MeS-Ph, 2,4-(F) ₂ -Ph, 4-Br-Ph] , [970 ! 4-MeS-Ph, 2,4-(F) ₂ -Ph, 4-Me-Ph] , [971 ! 4-MeS-Ph, 2,4- (F) ₂ -Ph, 4-iPr-Ph] , [972 ! 4-MeS-Ph, 2,4-(F) ₂ -Ph, 4-CF ₃ -Ph] , [973 ! 4-MeS-Ph, 2,4-(F) ₂ -Ph, 4-MeO-Ph] , [974 ! 4-MeS-Ph, 2,4-(F) ₂ -Ph, 4-Ph, Ph] , [975 ! 4-MeS-Ph, 2,4-(F) ₂ -Ph, 3,4- (Me) ₂ -Ph] , [976 ! 4-MeS-Ph, 2,4-(F) ₂ -Ph, 5-In] , [977 ! 4-MeS- Ph, 3,4- (Cl) ₂ -Ph, 2-Me-Ph] , [978 ! 4-MeS-Ph, 3,4-(Cl) ₂ -Ph, 3-F-Ph] , [979 ! 4-MeS-Ph, 3,4-(Cl) ₂ -Ph, 3-Me-Ph] , [980 ! 4- MeS-Ph, 3,4- (Cl) ₂ -Ph, 4-F-Ph] , [981 ! 4-MeS-Ph, 3,4-(Cl) ₂ -

Ph, 4-Cl-Ph] , [982 ! 4-MeS-Ph, 3,4-(Cl) ₂ -Ph, 4-Br-Ph] , [983 ; 4-MeS-Ph, 3,4-(Cl) ₂ -Ph, 4-Me-Ph] , [984 ! 4-MeS-Ph, 3,4- (Cl) ₂ -Ph, 4-iPr-Ph] , [985 ! 4-MeS-Ph, 3,4-(Cl) ₂ -Ph, 4-CF ₃ - Ph] , [986 ! 4-MeS-Ph, 3,4-(Cl) ₂ -Ph, 4 -MeO- Ph] , [987 ! 4-MeS- Ph, 3,4- (Cl) ₂ -Ph, 4-Ph, Ph] , [988 ! 4-MeS-Ph, 3,4-(Cl) ₂ -Ph, 3,4-(Me) ₂ -Ph] , [989 ! 4-MeS-Ph, 3,4-(Cl) ₂ -Ph, 5-In] , [990 ! 4-MeS-Ph, 3,5- (Cl) ₂ -Ph, 2-Me-Ph] , [991 ! 4-MeS-Ph, 3,5- (Cl) ₂ -Ph, 3-F-Ph] , [992 ! 4-MeS-Ph, 3,5-(Cl) ₂ -Ph, 3-Me-Ph] , [993 ! 4-MeS-Ph, 3,5-(Cl) ₂ -Ph, 4-F-Ph] , [994 ! 4-MeS-Ph, 3,5- (Cl) ₂ -Ph, 4-Cl-Ph] , [995 ! 4-MeS-Ph, 3,5-(Cl) ₂ -Ph, 4-Br-Ph] , [996 ! 4-MeS-Ph, 3,5-(Cl) ₂ -Ph, 4-Me-Ph] , [997 ! 4-MeS-Ph, 3,5- (Cl) ₂ -Ph, 4-iPr-Ph] , [998 ! 4-MeS-Ph, 3,5-(Cl) ₂ -Ph, 4- CF ₃ -Ph] , [999 ! 4-MeS-Ph, 3,5-(Cl) ₂ -Ph, 4-MeO-Ph] , [1000 ! 4- MeS-Ph, 3,5- (Cl) ₂ -Ph, 4-Ph, PhK

[1001 ! 4-MeS-Ph, 3,5-(Cl) ₂ -Ph, 3,4-(Me) ₂ -Ph] , [1002 ! 4-MeS- Ph, 3,5- (Cl) ₂ -Ph, 5-In] , [1003 ! 4-EtS-Ph, Ph,, Ph] , [1004 ! 4- CN-Ph, Ph^ Ph] , [1005 ! 4-CN-Ph, 2-F-Ph, 2-Me-Ph] , [1006 ! 4- CN-Ph, 2-F-Ph, 3-F-Ph] , [1007 ! 4-CN-Ph, 2-F-Ph, 3-Me-Ph] , [1008 ! 4-CN-Ph, 2-F-Ph, 4-F-Ph] , [1009 ! 4-CN-Ph, 2-F-Ph, 4- Cl-Ph] , [1010 ! 4-CN-Ph, 2-F-Ph, 4-Br-Ph] , [1011 ! 4-CN-Ph, 2-F-Ph, 4-Me-Ph] , [1012 ! 4-CN-Ph, 2-F-Ph, 4-iPr-Ph] , [1013 ; 4-CN-Ph, 2-F-Ph, 4-CF ₃ -Ph] , [1014 ! 4-CN-Ph, 2-F-Ph, 4- MeO-Ph] , [1015 ! 4-CN-Ph, 2-F-Ph, 4-Ph, Ph] , [1016 ! 4-CN-Ph, 2-F-Ph, 3,4-(Me) ₂ -Ph] , [1017 ! 4-CN-Ph, 2-F-Ph, 5-In] , [1018 ! 4-CN-Ph, 3-CF ₃ -Ph, 2-Me-Ph] , [1019 ! 4-CN-Ph, 3-CF ₃ -Ph, 3-

F-Ph] , [1020 ! 4-CN-Ph, 3-CF ₃ -Ph, 3-Me-Ph] , [1021 ! 4-CN-Ph, 3-CF ₃ -Ph, 4-F-Ph] , [1022 ! 4-CN-Ph, 3-CF ₃ -Ph, 4 -Cl -Ph] ,

[1023 ! 4-CN-Ph, 3-CF ₃ -Ph, 4-Br-Ph] , [1024 ! 4-CN-Ph, 3-CF ₃ - Ph, 4-Me-Ph] , [1025 ! 4-CN-Ph, 3-CF ₃ -Ph, 4-iPr-Ph] , [1026 ! 4-CN-Ph, 3-CF ₃ -Ph, 4-CF ₃ -Ph] , [1027 ! 4-CN-Ph, 3-CF ₃ -Ph, 4- MeO-Ph] , [1028 ! 4-CN-Ph, 3-CF ₃ -Ph, 4-Ph, Ph] , [1029 ! 4-CN- Ph, 3-CF ₃ -Ph, 3,4-(Me) ₂ -Ph] , [1030 ! 4-CN-Ph, 3-CF ₃ -Ph, 5- In] , [1031 ! 4-CN-Ph, 4-F-Ph, 2-Me-Ph] , [1032 ! 4-CN-Ph, 4-F- Ph, 3-F-Ph] , [1033 ! 4-CN-Ph, 4-F-Ph, 3-Me-Ph] , [1034 ! 4-CN- Ph, 4-F-Ph, 4-F-Ph] , [1035 ! 4-CN-Ph, 4-F-Ph, 4-Cl-Ph] ,

[1036 ! 4-CN-Ph, 4-F-Ph, 4-Br-Ph] , [1037 ! 4-CN-Ph, 4-F-Ph, 4-Me-Ph] , [1038 ! 4-CN-Ph, 4-F-Ph, 4-iPr-Ph] , [1039 ! 4-CN- Ph, 4-F-Ph, 4-CF ₃ -Ph] , [1040 ! 4-CN-Ph, 4-F-Ph, 4-MeO-Ph] ,

[1041 ! 4-CN-Ph, 4-F-Ph, 4-Ph, Ph] , [1042 ! 4-CN-Ph, 4-F-Ph, 3,4-(Me) ₂ -Ph] , [1043 ! 4-CN-Ph, 4-F-Ph, 5-In] , [1044 ! 4-CN- Ph, 4-iPr-Ph, 2-Me-Ph] , [1045 ! 4-CN-Ph, 4-iPr-Ph, 3-F-Ph] ,

[1046 ! 4-CN-Ph, 4-iPr-Ph, 3-Me-Ph] , [1047 ! 4-CN-Ph, 4-iPr- Ph, 4 -F-Ph] , [1048 ! 4-CN-Ph, 4-iPr-Ph, 4-Cl-Ph] , [1049 ! 4- CN-Ph, 4-iPr-Ph, 4-Br-Ph] , [1050 ! 4-CN-Ph, 4-iPr-Ph, 4-Me- Ph] , [1051 ! 4-CN-Ph, 4-iPr-Ph, 4-iPr-Ph] , [1052 ! 4-CN-Ph, 4-iPr-Ph, 4-CF ₃ -Ph], [1053!4-CN-Ph, 4-iPr-Ph, 4 -MeO-Ph] ,

[1054 ! 4-CN-Ph, 4-iPr-Ph, 4-Ph, Ph] , [1055 ! 4-CN-Ph, 4-iPr- Ph, 3,4-(Me) ₂ -Ph], [1056!4-CN-Ph, 4-iPr-Ph, 5-In], [1057! 4-CN-Ph, 4-CF ₃ -Ph, 2-Me-Ph], [1058!4-CN-Ph, 4-CF ₃ -Ph, 3-F- Ph], [1059!4-CN-Ph, 4-CF ₃ -Ph, 3-Me-Ph], [1060!4-CN-Ph, 4-

CF ₃ -Ph, 4-F-Ph] , [1061!4-CN-Ph, 4-CF ₃ -Ph, 4-Cl-Ph] , [1062 !4-CN-Ph, 4-CF ₃ -Ph, 4-Br-Ph], [1063!4-CN-Ph, 4-CF ₃ -Ph, 4- Me-Ph], [1064!4-CN-Ph, 4-CF ₃ -Ph, 4-iPr-Ph] , [1065 ! 4-CN- Ph, 4-CF ₃ -Ph, 4-CF ₃ -Ph], [1066!4-CN-Ph ₇ 4-CF ₃ -Ph, 4-MeO- Ph], [1067!4-CN-Ph, 4-CF ₃ -Ph, 4-Ph, Ph], [1068!4-CN-Ph, 4-CF ₃ -Ph, 3,4-(Me) ₂ -Ph], [1069!4-CN-Ph, 4-CF ₃ -Ph, 5-In], [1070 ! 4-CN-Ph, 4-Ph, Ph, 2-Me-Ph] , [1071 ! 4-CN-Ph, 4-Ph, Ph, 3-F-Ph], [1072!4-CN-Ph, 4-Ph, Ph, 3-Me-Ph], [1073! 4- CN-Ph, 4-Ph, Ph, 4-F-Ph] , [1074 ! 4-CN-Ph, 4-Ph, Ph, 4-C1- Ph] , [1075 ! 4-CN-Ph, 4-Ph, Ph, 4-Br-Ph] , [1076 ! 4-CN-Ph, 4- Ph, Ph, 4-Me-Ph] , [1077 ! 4-CN-Ph, 4-Ph, Ph, 4-iPr-Ph] , [1078!4-CN-Ph, 4-Ph, Ph, 4-CF ₃ -Ph], [1079!4-CN-Ph, 4-Ph, Ph, 4-MeO-Ph] , [1080 ! 4-CN-Ph, 4-Ph, Ph, 4-Ph, Ph] , [1081 ! 4-CN-Ph, 4-Ph, Ph, 3,4-(Me) ₂ -Ph], [1082!4-CN-Ph, 4-Ph, Ph, 5-In], [1083 !4-CN-Ph, 2,4-(F) ₂ -Ph, 2-Me-Ph], [1084 ! 4-CN- Ph, 2,4-(F) ₂ -Ph, 3-F-Ph] , [1085!4-CN-Ph, 2,4-(F) ₂ -Ph, 3- Me-Ph], [1086!4-CN-Ph, 2,4-(F) ₂ -Ph, 4-F-Ph], [1087 ! 4-CN- Ph, 2,4-(F) ₂ -Ph, 4-Cl-Ph] , [1088!4-CN-Ph, 2,4-(F) ₂ -Ph, 4- Br-Ph], [1089!4-CN-Ph, 2,4-(F) ₂ -Ph, 4-Me-Ph], [1090 ! 4-CN- Ph, 2,4-(F) ₂ -Ph, 4-iPr-Ph] , [1091!4-CN-Ph, 2,4-(F) ₂ -Ph, 4- CF ₃ -Ph], [1092!4-CN-Ph, 2,4-(F) ₂ -Ph, 4-MeO-Ph] , [1093 ! 4- CN-Ph, 2,4-(F) ₂ -Ph, 4-Ph, Ph], [1094!4-CN-Ph, 2,4-(F) ₂ -Ph, 3,4-(Me) ₂ -Ph], [1095!4-CN-Ph, 2,4-(F) ₂ -Ph, 5-In], [1096! 4-CN-Ph, 3,4- (Cl) ₂ -Ph, 2-Me-Ph], [1097!4-CN-Ph, 3,4- (Cl) ₂ - Ph, 3-F-Ph], [1098!4-CN-Ph, 3,4-(Cl) ₂ -Ph, 3-Me-Ph], [1099

! 4-CN-Ph, 3,4- (Cl) ₂ -Ph, 4-F-Ph] , [1100 14-CN-Ph, 3,4-

(Cl) ₂ -Ph, 4-Cl-PhK

[1101 ! 4-CN-Ph, 3,4-(Cl) ₂ -Ph, 4-Br-Ph] , [1102 ! 4-CN-Ph, 3,4- (Cl) ₂ -Ph, 4-Me-Ph] , [1103 ! 4-CN-Ph, 3,4-(Cl) ₂ -Ph, 4- iPr-Ph] , [1104 ! 4-CN-Ph, 3,4-(Cl) ₂ -Ph, 4-CF ₃ -Ph] , [1105 ! 4- CN-Ph, 3,4- (Cl) ₂ -Ph, 4 -MeO-Ph] , [1106 ! 4-CN-Ph, 3,4- (Cl) ₂ - Ph, 4-Ph, Ph] , [1107 ! 4-CN-Ph, 3,4-(Cl) ₂ -Ph, 3,4-(Me) ₂ -Ph] ,

[1108 ! 4-CN-Ph, 3,4- (Cl) ₂ -Ph, 5-In] , [1109 ! 4-CN-Ph, 3,5-

(Cl) ₂ -Ph, 2-Me-Ph] , [1110 ! 4-CN-Ph, 3,5-(Cl) ₂ -Ph, 3-F-PhJ ,

[1111 ! 4-CN-Ph, 3,5- (Cl) ₂ -Ph, 3-Me-Ph] , [1112 ! 4-CN-Ph, 3,5- (Cl) ₂ -Ph, 4-F-Ph] , [1113 ! 4-CN-Ph, 3,5-(Cl) ₂ -Ph, 4-Cl- Ph] , [1114 ! 4-CN-Ph, 3,5-(Cl) ₂ -Ph, 4-Br-Ph] , [1115 ! 4-CN- Ph, 3,5- (Cl) ₂ -Ph, 4-Me-Ph] , [1116 ! 4-CN-Ph, 3,5-(Cl) ₂ -Ph, 4-iPr-Ph] , [1117 ! 4-CN-Ph, 3,5-(Cl) ₂ -Ph, 4-CF ₃ -Ph] , [1118 ! 4-CN-Ph, 3,5- (Cl) ₂ -Ph, 4-MeO-Ph] , [1119 ! 4-CN-Ph, 3,5-

(Cl) ₂ -Ph, 4-Ph, Ph] , [1120 ! 4-CN-Ph, 3,5-(Cl) ₂ -Ph, 3,4-

(Me) ₂ -Ph] , [1121 ! 4-CN-Ph, 3,5-(Cl) ₂ -Ph, 5-In] , [1122 ! 4- MeNH-Ph, Ptu Ph] , [1123 ! 4-MeNH-Ph, 2-F-Ph, 2-Me-Ph] , [1124

! 4-MeNH-Ph, 2-F-Ph, 3-F-Ph] , [1125 ! 4-MeNH-Ph, 2-F-Ph, 3- Me-Ph] , [1126 ! 4-MeNH-Ph, 2-F-Ph, 4-F-Ph] , [1127 ! 4-MeNH- Ph, 2-F-Ph, 4-Cl-Ph] , [1128 ! 4-MeNH-Ph, 2-F-Ph, 4-Br-Ph] ,

[1129 ! 4-MeNH-Ph, 2-F-Ph, 4-Me-Ph] , [1130 ! 4-MeNH-Ph, 2-F- Ph, 4-iPr-Ph] , [1131 ! 4-MeNH-Ph, 2-F-Ph, 4-CF ₃ -Ph] , [1132 ! 4-MeNH-Ph, 2-F-Ph, 4-MeO-Ph] , [1133 ! 4-MeNH-Ph, 2-F-Ph, 4- Ph, Ph] , [1134 ! 4-MeNH-Ph, 2-F-Ph, 3,4-(Me) ₂ -Ph] , [1135 ! 4-

MeNH-Ph, 2-F-Ph, 5-In] , [1136 ! 4-MeNH-Ph, 3-CF ₃ -Ph, 2-Me- Ph] , [1137 ! 4-MeNH-Ph, 3-CF ₃ -Ph, 3-F-Ph] , [1138 ! 4-MeNH-Ph, 3-CF ₃ -Ph, 3-Me-Ph] , [1139 ! 4-MeNH-Ph, 3-CF ₃ -Ph, 4-F-Ph] , [1140 ! 4-MeNH-Ph, 3-CF ₃ -Ph, 4-Cl-Ph] , [1141 ! 4-MeNH-Ph, 3- CF ₃ -Ph, 4-Br-Ph] , [1142 ! 4-MeNH-Ph, 3-CF ₃ -Ph, 4-Me-Ph] , [1143 ! 4-MeNH-Ph, 3-CF ₃ -Ph, 4-iPr-Ph] , [1144 ! 4-MeNH-Ph, 3- CF ₃ -Ph, 4-CF ₃ -Ph] , [1145 ! 4-MeNH-Ph, 3-CF ₃ -Ph, 4-MeO-Ph] , [1146 ! 4-MeNH-Ph, 3-CF ₃ -Ph, 4-Ph, Ph] , [1147 ! 4-MeNH-Ph, 3- CF ₃ -Ph, 3,4-(Me) ₂ -Ph] , [1148 ! 4-MeNH-Ph, 3-CF ₃ -Ph, 5-In] , [1149 ! 4-MeNH-Ph, 4-F-Ph, 2-Me-Ph] , [1150 ! 4-MeNH-Ph, 4-F- Ph, 3-F-Ph] , [1151 ! 4-MeNH-Ph, 4-F-Ph, 3-Me-Ph] , [1152 ! 4- MeNH-Ph, 4-F-Ph, 4-F-Ph] , [1153 ! 4-MeNH-Ph, 4-F-Ph, 4-C1- Ph] , [1154 ! 4-MeNH-Ph, 4-F-Ph, 4-Br-Ph] , [1155 ! 4-MeNH-Ph, 4-F-Ph, 4-Me-Ph] , [1156 ! 4-MeNH-Ph, 4-F-Ph, 4-iPr-Ph] , [1157 ! 4-MeNH-Ph, 4-F-Ph, 4-CF ₃ -Ph] , [1158 ! 4-MeNH-Ph, 4-F- Ph, 4-MeO-Ph] , [1159 ! 4-MeNH-Ph, 4-F-Ph, 4-Ph, Ph] , [1160 ! 4-MeNH-Ph, 4-F-Ph, 3,4-(Me) ₂ -Ph] , [1161 ! 4-MeNH-Ph, 4-F-Ph, 5-In] , [1162 ! 4-MeNH-Ph, 4-iPr-Ph, 2-Me-Ph] , [1163 ! 4-MeNH- Ph, 4-iPr-Ph, 3-F-Ph] , [1164 ! 4-MeNH-Ph, 4-iPr-Ph, 3-Me- Ph] , [1165 ! 4-MeNH-Ph, 4-iPr-Ph, 4-F-Ph] , [1166 ! 4-MeNH-Ph, 4-iPr-Ph, 4-Cl-Ph] , [1167 ! 4-MeNH-Ph, 4-iPr-Ph, 4-Br-Ph] , [1168 ! 4-MeNH-Ph, 4-iPr-Ph, 4-Me-Ph] , [1169 ! 4-MeNH-Ph, 4- iPr-Ph, 4-iPr-Ph] , [1170 ! 4-MeNH-Ph, 4-iPr-Ph, 4-CF ₃ -Ph] , [1171 ! 4-MeNH-Ph, 4-iPr-Ph, 4-MeO-Ph] , [1172 ! 4-MeNH-Ph, 4- iPr-Ph, 4-Ph, Ph] , [1173 ! 4-MeNH-Ph, 4-iPr-Ph, 3,4-(Me) ₂ -

Ph] , [1174 : 4-MeNH-Ph, 4-iPr-Ph, 5-In] , [1175 ! 4-MeNH-Ph, 4-CF ₃ -Ph, 2-Me-Ph] , [1176 ! 4-MeNH-Ph, 4-CF ₃ -Ph, 3-F-Ph] ,

[1177 ! 4-MeNH-Ph, 4-CF ₃ -Ph, 3-Me-Ph] , [1178 ! 4-MeNH-Ph, 4- CF ₃ -Ph, 4-F-Ph] , [1179 ! 4-MeNH-Ph, 4-CF ₃ -Ph, 4-Cl-Ph] ,

[1180 ! 4-MeNH-Ph, 4-CF ₃ -Ph, 4-Br-Ph] , [1181 ! 4-MeNH-Ph, 4- CF ₃ -Ph, 4-Me-Ph] , [1182 ! 4-MeNH-Ph, 4-CF ₃ -Ph, 4-iPr-Ph] ,

[1183 ! 4-MeNH-Ph, 4-CF ₃ -Ph, 4-CF ₃ -Ph] , [1184 ! 4-MeNH-Ph, 4- CF ₃ -Ph, 4 -MeO-Ph] , [1185 ! 4-MeNH-Ph, 4-CF ₃ -Ph, 4-Ph, Ph] ,

[1186 ! 4-MeNH-Ph, 4-CF ₃ -Ph, 3,4-(Me) ₂ -Ph] , [1187 ! 4-MeNH- Ph, 4-CF ₃ -Ph, 5-In] , [1188 ! 4-MeNH-Ph, 4-Ph, Ph, 2-Me-Ph] ,

[1189 ! 4-MeNH-Ph, 4-Ph, Ph, 3-F-Ph] , [1190 ! 4-MeNH-Ph, 4- Ph, Ph, 3-Me-Ph] , [1191 ! 4-MeNH-Ph, 4-Ph, Ph, 4-F-Ph] ,

[1192 ! 4-MeNH-Ph, 4-Ph, Ph, 4-Cl-Ph] , [1193 ! 4-MeNH-Ph, 4- Ph, Ph, 4-Br-Ph] , [1194 ! 4-MeNH-Ph, 4-Ph, Ph, 4-Me-Ph] ,

[1195 ! 4-MeNH-Ph, 4-Ph, Ph, 4-iPr-Ph] , [1196 ! 4-MeNH-Ph, 4- Ph, Ph, 4-CF ₃ -Ph] , [1197 ! 4-MeNH-Ph, 4-Ph, Ph, 4 -MeO- Ph] ,

[1198 ! 4-MeNH-Ph, 4-Ph, Ph, 4-Ph, Ph] , [1199 ! 4-MeNH-Ph, 4- Ph, Ph, 3,4-(Me) ₂ -Ph] , [1200 ! 4-MeNH-Ph, 4-Ph, Ph, 5-InK

[1201 ! 4-MeNH-Ph, 2,4-(F) ₂ -Ph, 2-Me-Ph] , [1202 ! 4-MeNH-Ph, 2,4-(F) ₂ -Ph, 3-F-Ph] , [1203 ! 4-MeNH-Ph, 2,4-(F) ₂ -Ph, 3-Me- Ph] , [1204 ! 4-MeNH-Ph, 2,4-(F) ₂ -Ph, 4-F-Ph] , [1205 ! 4 -MeNH- Ph, 2,4-(F) ₂ -Ph, 4-Cl-Ph] , [1206 ! 4-MeNH-Ph, 2,4-(F) ₂ -Ph, 4-Br-Ph] , [1207 ! 4-MeNH-Ph, 2,4-(F) ₂ -Ph, 4-Me-Ph] , [1208 ! 4-MeNH-Ph, 2,4-(F) ₂ -Ph, 4-iPr-Ph] , [1209 ! 4-MeNH-Ph, 2,4-

(F) ₂ -Ph, 4-CF ₃ -Ph] , [1210 ! 4-MeNH-Ph, 2,4-(F) ₂ -Ph, 4-MeO-

Ph] , [1211 ! 4-MeNH-Ph, 2,4-(F) ₂ -Ph, 4-Ph, Ph] , [1212 ! 4- MeNH-Ph, 2,4-(F) ₂ -Ph, 3,4-(Me) ₂ -Ph] , [1213 ! 4-MeNH-Ph, 2,4-

(F) ₂ -Ph, 5-In] , [1214 ! 4-MeNH-Ph, 3,4-(Cl) ₂ -Ph, 2-Me-Ph] ,

[1215 ! 4-MeNH-Ph, 3,4-(Cl) ₂ -Ph, 3-F-Ph] , [1216 ! 4-MeNH-Ph, 3,4- (Cl) ₂ -Ph, 3-Me-Ph] , [1217 ! 4-MeNH-Ph, 3,4-(Cl) ₂ -Ph, 4- F-Ph] , [1218 ! 4-MeNH-Ph, 3,4-(Cl) ₂ -Ph, 4-Cl-Ph] , [1219 ! 4- MeNH-Ph, 3,4-(Cl) ₂ -Ph, 4-Br-Ph] , [1220 ! 4-MeNH-Ph, 3,4-

(Cl) ₂ -Ph, 4-Me-Ph] , [1221 ! 4-MeNH-Ph, 3,4-(Cl) ₂ -Ph, 4-iPr- Ph] , [1222 ! 4-MeNH-Ph, 3,4-(Cl) ₂ -Ph, 4-CF ₃ -Ph] , [1223 ! 4- MeNH-Ph, 3,4-(Cl) ₂ -Ph, 4-MeO-Ph] , [1224 ! 4-MeNH-Ph, 3,4-

(Cl) ₂ -Ph, 4-Ph, Ph] , [1225 ! 4-MeNH-Ph, 3,4-(Cl) ₂ -Ph, 3,4-

(Me) ₂ -Ph] , [1226 ! 4-MeNH-Ph, 3,4-(Cl) ₂ -Ph, 5-In] , [1227 ! 4- MeNH-Ph, 3,5-(Cl) ₂ -Ph, 2-Me-Ph] , [1228 ! 4-MeNH-Ph, 3,5-

(Cl) ₂ -Ph, 3-F-Ph] , [1229 ! 4-MeNH-Ph, 3,5-(Cl) ₂ -Ph, 3-Me- Ph] , [1230 ! 4-MeNH-Ph, 3,5-(Cl) ₂ -Ph, 4-F-Ph] , [1231 ! 4- MeNH-Ph, 3,5-(Cl) ₂ -Ph, 4-Cl-Ph] , [1232 ! 4-MeNH-Ph, 3,5-

(Cl) ₂ -Ph, 4-Br-Ph] , [1233 ! 4-MeNH-Ph, 3,5-(Cl) ₂ -Ph, 4-Me- Ph] , [1234 ! 4-MeNH-Ph, 3,5-(Cl) ₂ -Ph, 4-iPr-Ph] , [1235 ! 4- MeNH-Ph, 3,5-(Cl) ₂ -Ph, 4-CF ₃ -Ph] , [1236 ! 4-MeNH-Ph, 3,5-

(Cl) ₂ -Ph, 4 -MeO-Ph] , [1237 ! 4-MeNH-Ph, 3,5-(Cl) ₂ -Ph, 4-Ph, Ph] , [1238 ! 4-MeNH-Ph, 3,5-(Cl) ₂ -Ph, 3,4-(Me) ₂ -Ph] , [1239 ! 4-MeNH-Ph, 3,5-(Cl) ₂ -Ph, 5-In] , [1240 ! 4-EtNH-Ph, Ph _λ Ph] ,

[1241 ! 4-AcNH-Ph, Ph _> Ph] , [1242 ! 4-AcNH-Ph, 2-F-Ph, 2-Me- Ph] , [1243 ! 4-AcNH-Ph, 2-F-Ph, 3-F-Ph] , [1244 ! 4-AcNH-Ph, 2-F-Ph, 3-Me-Ph] , [1245 ! 4-AcNH-Ph, 2-F-Ph, 4-F-Ph] , [1246

I 4-AcNH-Ph, 2-F-Ph, 4-Cl-Ph] , [1247 I 4-AcNH-Ph, 2-F-Ph, 4- Br-Ph] , [1248 ! 4-AcNH-Ph, 2-F-Ph, 4-Me-Ph] , [1249 ! 4-AcNH- Ph, 2-F-Ph, 4-iPr-Ph] , [1250 ! 4-AcNH-Ph, 2-F-Ph, 4-CF ₃ -Ph] , [1251 : 4-AcNH-Ph, 2-F-Ph, 4-MeO-Ph] , [1252 ! 4-AcNH-Ph, 2-F- Ph, 4-Ph, Ph] , [1253 ! 4-AcNH-Ph, 2-F-Ph, 3,4-(Me) ₂ -Ph] , [1254 ! 4-AcNH-Ph, 2-F-Ph, 5-In] , [1255 ! 4-AcNH-Ph, 3-CF ₃ - Ph, 2-Me-Ph] , [1256 ! 4-AcNH-Ph, 3-CF ₃ -Ph, 3-F-Ph] , [1257 ! 4-AcNH-Ph, 3-CF ₃ -Ph, 3-Me-Ph] , [1258 ! 4-AcNH-Ph, 3-CF ₃ -Ph, 4-F-Ph] , [1259 ! 4-AcNH-Ph, 3-CF ₃ -Ph, 4-Cl-Ph] , [1260 ! 4- AcNH-Ph, 3-CF ₃ -Ph, 4-Br-Ph] , [1261 ! 4-AcNH-Ph, 3-CF ₃ -Ph, 4- Me-Ph] , [1262 ! 4-AcNH-Ph, 3-CF ₃ -Ph, 4-iPr-Ph] , [1263 ! 4- AcNH-Ph, 3-CF ₃ -Ph, 4-CF ₃ -Ph] , [1264 ! 4-AcNH-Ph, 3-CF ₃ -Ph, 4 -MeO-Ph] , [1265 ! 4-AcNH-Ph, 3-CF ₃ -Ph, 4-Ph, Ph] , [1266 ! 4- AcNH-Ph, 3-CF ₃ -Ph, 3,4-(Me) ₂ -Ph] , [1267 ! 4-AcNH-Ph, 3-CF ₃ - Ph, 5-In] , [1268 ! 4-AcNH-Ph, 4-F-Ph, 2-Me-Ph] , [1269 ! 4- AcNH-Ph, 4-F-Ph, 3-F-Ph] , [1270 ! 4-AcNH-Ph, 4-F-Ph, 3-Me- Ph] , [1271 ! 4-AcNH-Ph, 4-F-Ph, 4-F-Ph] , [1272 ! 4-AcNH-Ph, 4-F-Ph, 4-Cl-Ph] , [1273 ! 4-AcNH-Ph, 4-F-Ph, 4-Br-Ph] , [1274 ! 4-AcNH-Ph, 4-F-Ph, 4-Me-Ph] , [1275 ! 4-AcNH-Ph, 4-F-Ph, 4- iPr-Ph] , [1276 ! 4-AcNH-Ph, 4-F-Ph, 4-CF ₃ -Ph] , [1277 ! 4- AcNH-Ph, 4-F-Ph, 4-MeO-Ph] , [1278 ! 4-AcNH-Ph, 4-F-Ph, 4-Ph, Ph] , [1279 ! 4-AcNH-Ph, 4-F-Ph, 3,4-(Me) ₂ -Ph] , [1280 ! 4- AcNH-Ph, 4-F-Ph, 5-In] , [1281 ! 4-AcNH-Ph, 4-iPr-Ph, 2-Me- Ph] , [1282 ! 4-AcNH-Ph, 4-iPr-Ph, 3-F-Ph] , [1283 ! 4-AcNH-Ph, 4-iPr-Ph, 3-Me-Ph] , [1284 ! 4-AcNH-Ph, 4-iPr-Ph, 4-F-Ph] ,

[1285 I 4-AcNH-Ph, 4-iPr-Ph, 4-Cl-Ph] , [1286 ! 4-AcNH-Ph, 4- iPr-Ph, 4-Br-Ph] , [1287 ! 4-AcNH-Ph, 4-iPr-Ph, 4-Me-Ph] , [1288 : 4-AcNH-Ph, 4-iPr-Ph, 4-iPr-Ph] , [1289 ! 4-AcNH-Ph, 4- iPr-Ph, 4-CF ₃ -Ph] , [1290 ! 4-AcNH-Ph, 4-iPr-Ph, 4 -MeO- Ph] , [1291 ! 4-AcNH-Ph, 4-iPr-Ph, 4-Ph, Ph] , [1292. ^' 4-AcNH-Ph, 4- iPr-Ph, 3,4-(Me) ₂ -Ph] , [1293 ! 4-AcNH-Ph, 4-iPr-Ph, 5-In] , [1294 ! 4-AcNH-Ph, 4-CF ₃ -Ph, 2-Me-Ph] , [1295 ! 4-AcNH-Ph, 4- CF ₃ -Ph, 3-F-Ph] , [1296 ! 4-AcNH-Ph, 4-CF ₃ -Ph, 3-Me-Ph] , [1297 ! 4-AcNH-Ph, 4-CF ₃ -Ph, 4-F-Ph] , [1298 ! 4-AcNH-Ph, 4- CF ₃ -Ph, 4-Cl-Ph] , [1299 ! 4-AcNH-Ph, 4-CF ₃ -Ph, 4-Br-Ph] , [1300 ! 4-AcNH-Ph, 4-CF ₃ -Ph, 4-Me-Ph] _λ

[1301 ! 4-AcNH-Ph, 4-CF ₃ -Ph, 4-iPr-Ph] , [1302 ! 4-AcNH-Ph, 4- CF ₃ -Ph, 4-CF ₃ -Ph] , [1303 ! 4-AcNH-Ph, 4-CF ₃ -Ph, 4-MeO-Ph] , [1304 ! 4-AcNH-Ph, 4-CF ₃ -Ph, 4-Ph, Ph] , [1305 ! 4-AcNH-Ph, 4- CF ₃ -Ph, 3,4-(Me) ₂ -Ph] , [1306. ^' 4-AcNH-Ph, 4-CF ₃ -Ph, 5-In] , [1307 ! 4-AcNH-Ph, 4-Ph, Ph, 2-Me-Ph] , [1308 ! 4-AcNH-Ph, 4- Ph, Ph, 3-F-Ph] , [1309 '.4-AcNH-Ph, 4-Ph, Ph, 3-Me-Ph] , [1310 ! 4-AcNH-Ph, 4-Ph, Ph, 4-F-Ph] , [1311 ! 4-AcNH-Ph, 4- Ph, Ph, 4-Cl-Ph] , [1312 ! 4-AcNH-Ph, 4-Ph, Ph, 4-Br-Ph] , [1313 ! 4-AcNH-Ph, 4-Ph, Ph, 4-Me-Ph] , [1314 ! 4-AcNH-Ph, 4- Ph, Ph, 4-iPr-Ph] , [1315 ! 4-AcNH-Ph, 4-Ph, Ph, 4-CF ₃ -Ph] , [1316 ! 4-AcNH-Ph, 4-Ph, Ph, 4-MeO-Ph] , [1317 ! 4-AcNH-Ph, 4- Ph, Ph, 4-Ph, Ph] , [1318 ! 4-AcNH-Ph, 4-Ph, Ph, 3,4- (Me) ₂ - Ph] , [1319 ! 4-AcNH-Ph, 4-Ph, Ph, 5-In] , [1320 ! 4-AcNH-Ph, 2,4-(F) ₂ -Ph, 2-Me-Ph] , [1321 ! 4-AcNH-Ph, 2,4-(F) ₂ -Ph, 3-F-

Ph] , [1322 ! 4-AcNH-Ph, 2,4-(F) ₂ -Ph, 3-Me-Ph] , [1323 ! 4- AcNH-Ph, 2,4-(F) ₂ -Ph, 4-F-Ph] , [1324 ! 4-AcNH-Ph, 2,4- (F) ₂ - Ph, 4-Cl-Ph] , [1325 ! 4-AcNH-Ph, 2,4-(F) ₂ -Ph, 4-Br-Ph] ,

[1326 ! 4-AcNH-Ph, 2,4-(F) ₂ -Ph, 4-Me-Ph] , [1327 ! 4-AcNH-Ph, 2,4-(F) ₂ -Ph, 4-iPr-Ph] , [1328 ! 4-AcNH-Ph, 2,4-(F) ₂ -Ph, 4- CF ₃ -Ph] , [1329 ! 4-AcNH-Ph, 2,4-(F) ₂ -Ph, 4-MeO-Ph] , [1330 ! 4-AcNH-Ph, 2,4-(F) ₂ -Ph, 4-Ph, Ph] , [1331 ! 4-AcNH-Ph, 2,4-

(F) ₂ -Ph, 3,4-(Me) ₂ -Ph] , [1332 ! 4-AcNH-Ph, 2,4-(F) ₂ -Ph, 5- In] , [1333 ! 4-AcNH-Ph, 3,4-(Cl) ₂ -Ph, 2-Me-Ph] , [1334 ! 4- AcNH-Ph, 3,4- (Cl) ₂ -Ph, 3-F-Ph] , [1335 ! 4-AcNH-Ph, 3,4-

(Cl) ₂ -Ph, 3-Me-Ph] , [1336 ! 4-AcNH-Ph, 3,4-(Cl) ₂ -Ph, 4-F- Ph] , [1337 ! 4-AcNH-Ph, 3,4-(Cl) ₂ -Ph, 4-Cl-Ph] , [1338 ! 4- AcNH-Ph, 3,4- (Cl) ₂ -Ph, 4-Br-Ph] , [1339 ! 4-AcNH-Ph, 3,4-

(Cl) ₂ -Ph, 4-Me-Ph] , [1340 ! 4-AcNH-Ph, 3,4-(Cl) ₂ -Ph, 4-iPr- Ph] , [1341 ! 4-AcNH-Ph, 3,4-(Cl) ₂ -Ph, 4-CF ₃ -Ph] , [1342 ! 4- AcNH-Ph, 3,4- (Cl) ₂ -Ph, 4-MeO-Ph] , [1343 ! 4-AcNH-Ph, 3,4-

(Cl) ₂ -Ph, 4-Ph, Ph] , [1344 ! 4-AcNH-Ph, 3,4-(Cl) ₂ -Ph, 3,4-

(Me) ₂ -Ph] , [1345 ! 4-AcNH-Ph, 3,4-(Cl) ₂ -Ph, 5-In] , [1346 ! 4- AcNH-Ph, 3,5- (Cl) ₂ -Ph, 2-Me-Ph] , [1347 ! 4-AcNH-Ph, 3,5-

(Cl) ₂ -Ph, 3-F-Ph] , [1348 ! 4-AcNH-Ph, 3,5-(Cl) ₂ -Ph, 3-Me-

Ph] , [1349 ! 4-AcNH-Ph, 3,5-(Cl) ₂ -Ph, 4-F-Ph] , [1350 ! 4- AcNH-Ph, 3,5- (Cl) ₂ -Ph, 4-Cl-Ph] , [1351 ! 4-AcNH-Ph, 3,5-

(Cl) ₂ -Ph, 4-Br-Ph] , [1352 ! 4-AcNH-Ph, 3,5-(Cl) ₂ -Ph, 4-Me-

Ph] , [1353 ! 4-AcNH-Ph, 3,5-(Cl) ₂ -Ph, 4-iPr-Ph] , [1354 ! 4- AcNH-Ph, 3,5- (Cl) ₂ -Ph, 4-CF ₃ -Ph] , [1355 ! 4-AcNH-Ph, 3,5-

(Cl) ₂ -Ph, 4 -MeO-Ph] , [1356 ! 4-AcNH-Ph, 3,5-(Cl) ₂ -Ph, 4-Ph, Ph] , [1357 ! 4-AcNH-Ph, 3,5-(Cl) ₂ -Ph, 3,4-(Me) ₂ -Ph] , [1358 ! 4-AcNH-Ph, 3,5- (Cl) ₂ "Ph, 5-In] , [1359 ! 4-MeOC (=0) -Ph, Pfcu Ph] , [1360 : 4-NH ₂ C(=0) -Ph, Ph,, Ph] , [1361 ^* .4-MeNHC (=0) -Ph, Ph _^ Ph] , [1362 ! 2,3-(Cl) ₂ -Ph, Ptu Ph] , [1363 ! 2,3-(Cl) ₂ -Ph, 2-F-Ph, 2-Me-Ph] , [1364 ! 2,3-(Cl) ₂ -Ph, 2-F-Ph, 3-F-Ph] ,

[1365 ! 2,3-(Cl) ₂ -Ph, 2-F-Ph, 3-Me-Ph] , [1366 ! 2,3-(Cl) ₂ -Ph, 2-F-Ph, 4-F-Ph] , [1367 ! 2,3-(Cl) ₂ -Ph, 2-F-Ph, 4-Cl-Ph] ,

[1368 ! 2,3-(Cl) ₂ -Ph, 2-F-Ph, 4-Br-Ph] , [1369 ! 2,3-(Cl) ₂ -Ph, 2-F-Ph, 4-Me-Ph] , [1370 ! 2,3-(Cl) ₂ -Ph, 2-F-Ph, 4-iPr-Ph] ,

[1371 ! 2,3-(Cl) ₂ -Ph, 2-F-Ph, 4-CF ₃ -Ph] , [1372 ! 2,3-(Cl) ₂ - Ph, 2-F-Ph, 4 -MeO-Ph] , [1373 ! 2,3-(Cl) ₂ -Ph, 2-F-Ph, 4-Ph, Ph] , [1374 ! 2,3-(Cl) ₂ -Ph, 2-F-Ph, 3,4-(Me) ₂ -Ph] , [1375 ! 2,3- (Cl) ₂ -Ph, 2-F-Ph, 5-In] , [1376 ! 2,3-(Cl) ₂ -Ph, 3-CF ₃ -Ph, 2-Me-Ph] , [1377 ! 2,3-(Cl) ₂ -Ph, 3-CF ₃ -Ph, 3-F-Ph] , [1378 ! 2,3- (Cl) ₂ -Ph, 3-CF ₃ -Ph, 3-Me-Ph] , [1379 ! 2,3-(Cl) ₂ -Ph, 3- CF ₃ -Ph, 4-F-Ph] , [1380 ! 2,3-(Cl) ₂ -Ph, 3-CF ₃ -Ph, 4 -Cl-Ph] ,

[1381 ! 2,3-(Cl) ₂ -Ph, 3-CF ₃ -Ph, 4-Br-Ph] , [1382 ! 2,3-(Cl) ₂ - Ph, 3-CF ₃ -Ph, 4-Me-Ph] , [1383 ! 2,3-(Cl) ₂ -Ph, 3-CF ₃ -Ph, 4- iPr-Ph] , [1384 ! 2,3-(Cl) ₂ -Ph, 3-CF ₃ -Ph, 4-CF ₃ -Ph] , [1385 ! 2,3- (Cl) ₂ -Ph, 3-CF ₃ -Ph, 4 -MeO- Ph] , [1386 ! 2,3-(Cl) ₂ -Ph, 3- CF ₃ -Ph, 4-Ph, Ph] , [1387 ! 2,3-(Cl) ₂ -Ph, 3-CF ₃ -Ph, 3,4-

(Me) ₂ -Ph] , [1388. ^' 2,3-(Cl) ₂ -Ph, 3-CF ₃ -Ph, 5-In] , [1389 ! 2,3- (Cl) ₂ -Ph, 4-F-Ph, 2-Me-Ph] , [1390 ! 2,3-(Cl) ₂ -Ph, 4-F- Ph, 3-F-Ph] , [1391 ! 2,3-(Cl) ₂ -Ph, 4-F-Ph, 3-Me-Ph] , [1392 !

2,3- (Cl) ₂ -Ph, 4-F-Ph, 4-F-Ph] , [1393 ! 2,3-(Cl) ₂ -Ph, 4-F-Ph, 4-Cl-Ph] , [1394 ! 2,3-(Cl) ₂ -Ph, 4-F-Ph, 4-Br-Ph] , [1395 ! 2,3- (Cl) ₂ -Ph, 4-F-Ph, 4-Me-Ph] , [1396 ! 2,3-(Cl) ₂ -Ph, 4-F- Ph, 4-iPr-Ph] , [1397 ! 2,3-(Cl) ₂ -Ph, 4-F-Ph, 4-CF ₃ -Ph] , [1398 ! 2,3-(Cl) ₂ -Ph, 4-F-Ph, 4 -MeO- Ph] , [1399 ! 2,3-(Cl) ₂ - Ph, 4-F-Ph, 4-Ph, Ph] , [1400 ! 2,3-(Cl) ₂ -Ph, 4-F-Ph, 3,4- (Me) ₂ -Ph] _^

[1401!2,3-(Cl) ₂ -Ph, 4-F-Ph, 5-In], [1402!2,3-(Cl) ₂ -Ph, 4- iPr-Ph, 2-Me-Ph], [1403!2,3-(Cl) ₂ -Ph, 4-iPr-Ph, 3-F-Ph], [1404!2,3-(Cl) ₂ -Ph, 4-iPr-Ph, 3-Me-Ph], [1405!2,3-(Cl) ₂ - Ph, 4-iPr-Ph, 4-F-Ph] , [1406!2,3-(Cl) ₂ -Ph, 4-iPr-Ph, 4-Cl- Ph], [1407!2,3-(Cl) ₂ -Ph, 4-iPr-Ph, 4-Br-Ph], [1408 ^' .2,3- (Cl) ₂ -Ph, 4-iPr-Ph, 4-Me-Ph], [1409!2,3-(Cl) ₂ -Ph, 4-iPr- Ph, 4-iPr-Ph] , [1410!2,3-(Cl) ₂ -Ph, 4-iPr-Ph, 4-CF ₃ -Ph], [1411!2,3-(Cl) ₂ -Ph, 4-iPr-Ph, 4 -MeO-Ph] , [1412!2,3-(Cl) ₂ - Ph, 4-iPr-Ph, 4-Ph, Ph], [1413 !2,3-(Cl) ₂ -Ph, 4-iPr-Ph, 3,4-(Me) ₂ -Ph], [1414!2,3-(Cl) ₂ -Ph, 4-iPr-Ph, 5-In], [1415 !2,3-(Cl) ₂ -Ph, 4-CF ₃ -Ph, 2-Me-Ph], [1416!2,3-(Cl) ₂ -Ph, 4- CF ₃ -Ph, 3-F-Ph] , [1417!2,3-(Cl) ₂ -Ph, 4-CF ₃ -Ph, 3-Me-Ph], [1418!2,3-(Cl) ₂ -Ph, 4-CF ₃ -Ph, 4-F-Ph] , [1419!2,3-(Cl) ₂ - Ph, 4-CF ₃ -Ph, 4-Cl-Ph] , [1420!2,3-(Cl) ₂ -Ph, 4-CF ₃ -Ph, 4- Br-Ph], [1421!2,3-(Cl) ₂ -Ph, 4-CF ₃ -Ph, 4-Me-Ph], [1422! 2,3- (Cl) ₂ -Ph, 4-CF ₃ -Ph, 4-iPr-Ph] , [1423!2,3-(Cl) ₂ -Ph, 4- CF ₃ -Ph, 4-CF ₃ -Ph], [1424!2,3-(Cl) ₂ -Ph, 4-CF ₃ -Ph, 4-MeO- Ph], [1425!2,3-(Cl) ₂ -Ph, 4-CF ₃ -Ph, 4-Ph, Ph], [1426! 2,3-

(Cl) ₂ -Ph, 4-CF ₃ -Ph, 3,4-(Me) ₂ -Ph] , [1427 ! 2,3-(Cl) ₂ -Ph, 4- CF ₃ -Ph, 5-In] , [1428 ! 2,3-(Cl) ₂ -Ph, 4-Ph, Ph, 2-Me-Ph] ,

[1429 ! 2,3-(Cl) ₂ -Ph, 4-Ph, Ph, 3-F-Ph] , [1430 ! 2,3-(Cl) ₂ - Ph, 4-Ph, Ph, 3-Me-Ph] , [1431 ! 2,3-(Cl) ₂ -Ph, 4-Ph, Ph, 4-F- Ph] , [1432 ! 2,3-(Cl) ₂ -Ph, 4-Ph, Ph, 4-Cl-Ph] , [1433 ! 2,3-

(Cl) ₂ -Ph, 4-Ph, Ph, 4-Br-Ph] , [1434 ! 2,3-(Cl) ₂ -Ph, 4-Ph, Ph, 4-Me-Ph] , [1435 ! 2,3-(Cl) ₂ -Ph, 4-Ph, Ph, 4-iPr-Ph] ,

[1436 ! 2,3-(Cl) ₂ -Ph, 4-Ph, Ph, 4-CF ₃ -Ph] , [1437 ! 2,3-(Cl) ₂ - Ph, 4-Ph, Ph, 4 -MeO-Ph] , [1438 ! 2,3-(Cl) ₂ -Ph, 4-Ph, Ph, 4- Ph, Ph] , [1439 ! 2,3-(Cl) ₂ -Ph, 4-Ph, Ph, 3,4-(Me) ₂ -Ph] ,

[1440 ! 2,3-(Cl) ₂ -Ph, 4-Ph, Ph, 5-In] , [1441 ! 2,3-(Cl) ₂ -Ph, 2,4-(F) ₂ -Ph, 2-Me-Ph] , [1442 ! 2,3-(Cl) ₂ -Ph, 2,4-(F) ₂ -Ph, 3- F-Ph] , [1443 ! 2,3-(Cl) ₂ -Ph, 2,4-(F) ₂ -Ph, 3-Me-Ph] , [1444 ! 2,3- (Cl) ₂ -Ph, 2,4-(F) ₂ -Ph, 4-F-Ph] , [1445 ! 2,3-(Cl) ₂ -Ph, 2,4-(F) ₂ -Ph, 4-Cl-Ph] , [1446 ! 2,3-(Cl) ₂ -Ph, 2,4-(F) ₂ -Ph, 4- Br-Ph] , [1447 ! 2,3-(Cl) ₂ -Ph, 2,4-(F) ₂ -Ph, 4-Me-Ph] , [1448 ! 2,3- (Cl) ₂ -Ph, 2,4-(F) ₂ -Ph, 4-iPr-Ph] , [1449 ! 2,3-(Cl) ₂ -Ph, 2,4-(F) ₂ -Ph, 4-CF ₃ -Ph] , [1450 ! 2,3-(Cl) ₂ -Ph, 2,4-(F) ₂ -Ph, 4-MeO-Ph] , [1451 ! 2,3-(Cl) ₂ -Ph, 2,4-(F) ₂ -Ph, 4-Ph, Ph] ,

[1452 ! 2,3-(Cl) ₂ -Ph, 2,4-(F) ₂ -Ph, 3,4-(Me) ₂ -Ph] , [1453 ! 2,3- (Cl) ₂ -Ph, 2,4-(F) ₂ -Ph, 5-In] , [1454 ! 2,3-(Cl) ₂ -Ph, 3,4-

(Cl) ₂ -Ph, 2-Me-Ph] , [1455 ! 2,3-(Cl) ₂ -Ph, 3,4-(Cl) ₂ -Ph, 3-F- Ph] , [1456 ! 2,3-(Cl) ₂ -Ph, 3,4-(Cl) ₂ -Ph, 3-Me-Ph] , [1457 ! 2,3- (Cl) ₂ -Ph, 3,4- (Cl) ₂ -Ph, 4-F-Ph] , [1458 ! 2,3-(Cl) ₂ -Ph, 3,4- (Cl) ₂ -Ph, 4-Cl-Ph] , [1459 ! 2,3-(Cl) ₂ -Ph, 3,4-(Cl) ₂ -Ph,

4-Br-Ph] , [1460 ! 2,3-(Cl) ₂ -Ph, 3,4-(Cl) ₂ -Ph, 4-Me-Ph] , [1461 ! 2,3-(Cl) ₂ -Ph, 3,4-(Cl) ₂ -Ph, 4-iPr-Ph] , [1462 ! 2,3- (Cl) ₂ -Ph, 3,4- (Cl) ₂ -Ph, 4-CF ₃ -Ph] , [1463 ! 2,3-(Cl) ₂ -Ph, 3,4- (Cl) ₂ -Ph, 4 -MeO-Ph] , [1464 ! 2,3-(Cl) ₂ -Ph, 3,4-(Cl) ₂ -Ph, 4-Ph, Ph] , [1465 ! 2,3-(Cl) ₂ -Ph, 3,4-(Cl) ₂ -Ph, 3, 4-(Me) ₂ - Ph] , [1466 ! 2,3-(Cl) ₂ -Ph, 3,4-(Cl) ₂ -Ph, 5-In] , [1467 ! 2,3- (Cl) ₂ -Ph, 3,5- (Cl) ₂ -Ph, 2-Me-Ph] , [1468 ! 2,3-(Cl) ₂ -Ph, 3,5- (Cl) ₂ -Ph, 3-F-Ph] , [1469 ! 2,3-(Cl) ₂ -Ph, 3,5-(Cl) ₂ -Ph, 3-Me- Ph] , [1470 ! 2,3-(Cl) ₂ -Ph, 3,5-(Cl) ₂ -Ph, 4-F-Ph] , [1471 ! 2,3- (Cl) ₂ -Ph, 3,5- (Cl) ₂ -Ph, 4-Cl-Ph] , [1472 ! 2,3-(Cl) ₂ -Ph, 3,5- (Cl) ₂ -Ph, 4-Br-Ph] , [1473 ! 2,3-(Cl) ₂ -Ph, 3,5-(Cl) ₂ -Ph, 4-Me-Ph] , [1474 ! 2,3-(Cl) ₂ -Ph, 3,5-(Cl) ₂ -Ph, 4-iPr-Ph] , [1475 ! 2,3-(Cl) ₂ -Ph, 3,5-(Cl) ₂ -Ph, 4-CF ₃ -Ph] , [1476 ! 2,3- (Cl) ₂ -Ph, 3,5- (Cl) ₂ -Ph, 4-MeO-Ph] , [1477 ! 2,3-(Cl) ₂ -Ph, 3,5- (Cl) ₂ -Ph, 4-Ph, Ph] , [1478 ! 2,3-(Cl) ₂ -Ph, 3,5-(Cl) ₂ -Ph, 3,4-(Me) ₂ -Ph] , [1479 ! 2,3-(Cl) ₂ -Ph, 3,5-(Cl) ₂ -Ph, 5-In] , [1480 ! 2,6-(F) ₂ -Ph, Ph _> Ph] , [1481 ! 3,4-(F) ₂ -Ph, Ph^ Ph] , [1482 ! 3,4-(F) ₂ -Ph, 2-F-Ph, 2-Me-Ph] , [1483 ! 3,4-(F) ₂ -Ph, 2-F-Ph, 3-F-Ph] , [1484 ! 3,4-(F) ₂ -Ph, 2-F-Ph, 3-Me-Ph] , [1485 ! 3,4-(F) ₂ -Ph, 2-F-Ph, 4-F-Ph] , [1486 ! 3,4-(F) ₂ -Ph, 2- F-Ph, 4-Cl-Ph] , [1487 ! 3,4-(F) ₂ -Ph, 2-F-Ph, 4-Br-Ph] , [1488 ! 3,4-(F) ₂ -Ph, 2-F-Ph, 4-Me-Ph] , [1489 ! 3,4-(F) ₂ -Ph, 2-F- Ph, 4-iPr-Ph] , [1490 ! 3,4-(F) ₂ -Ph ₇ 2-F-Ph, 4-CF ₃ -Ph] , [1491 ! 3,4-(F) ₂ -Ph, 2-F-Ph, 4 -MeO-Ph] , [1492 ! 3,4-(F) ₂ -Ph, 2-F- Ph, 4-Ph, Ph] , [1493 ! 3,4-(F) ₂ -Ph, 2-F-Ph, 3,4-(Me) ₂ -Ph] ,

[1494 ! 3,4-(F) ₂ -Ph, 2-F-Ph, 5-In] , [1495 ! 3,4-(F) ₂ -Ph, 3- CF ₃ -Ph, 2-Me-Ph] , [1496 ! 3,4-(F) ₂ -Ph, 3-CF ₃ -Ph, 3 -F-Ph] , [1497 ! 3,4-(F) ₂ -Ph, 3-CF ₃ -Ph, 3-Me-Ph] , [1498 ! 3,4-(F) ₂ -Ph, 3-CF ₃ -Ph, 4-F-Ph] , [1499 ! 3,4-(F) ₂ -Ph, 3-CF ₃ -Ph, 4-Cl-Ph] , [1500 ! 3,4-(F) ₂ -Ph, 3-CF ₃ -Ph, 4-Br-PhK

[1501!3,4-(F) ₂ -Ph, 3-CF ₃ -Ph, 4-Me-Ph], [1502!3,4-(F) ₂ -Ph, 3-CF ₃ -Ph, 4-iPr-Ph] , [1503!3,4-(F) ₂ -Ph, 3-CF ₃ -Ph, 4-CF ₃ - Ph], [1504!3,4-(F) ₂ -Ph, 3-CF ₃ -Ph, 4-MeO-Ph], [1505 ! 3,4- (F) ₂ -Ph, 3-CF ₃ -Ph, 4-Ph, Ph], [1506!3,4-(F) ₂ -Ph, 3-CF ₃ -Ph, 3,4-(Me) ₂ -Ph], [1507!3,4-(F) ₂ -Ph, 3-CF ₃ -Ph, 5-In], [1508! 3,4-(F) ₂ -Ph, 4-F-Ph, 2-Me-Ph], [1509!3,4-(F) ₂ -Ph, 4-F-Ph, 3-F-Ph], [1510!3,4-(F) ₂ -Ph, 4-F-Ph, 3-Me-Ph], [1511 ! 3,4- (F) ₂ -Ph, 4-F-Ph, 4-F-Ph] , [1512!3,4-(F) ₂ -Ph, 4-F-Ph, 4-Cl- Ph], [1513!3,4-(F) ₂ -Ph, 4-F-Ph, 4-Br-Ph], [1514!3,4-(F) ₂ - Ph, 4-F-Ph, 4-Me-Ph], [1515!3,4-(F) ₂ -Ph, 4-F-Ph, 4-iPr- Ph], [1516!3,4-(F) ₂ -Ph, 4-F-Ph, 4-CF ₃ -Ph], [1517 ! 3,4- (F) ₂ -Ph, 4-F-Ph, 4-MeO-Ph] , [1518!3,4-(F) ₂ -Ph, 4-F-Ph, 4- Ph, Ph], [1519!3,4-(F) ₂ -Ph, 4-F-Ph, 3,4-(Me) ₂ -Ph], [1520! 3,4-(F) ₂ -Ph, 4-F-Ph, 5-In], [1521!3,4-(F) ₂ -Ph, 4-iPr-Ph, 2-Me-Ph], [1522!3,4-(F) ₂ -Ph, 4-iPr-Ph, 3-F-Ph] , [1523 ! 3,4-(F) ₂ -Ph, 4-iPr-Ph, 3-Me-Ph], [1524!3,4-(F) ₂ -Ph, 4-iPr- Ph, 4-F-Ph] , [1525!3,4-(F) ₂ -Ph, 4-iPr-Ph, 4-Cl-Ph] , [1526 !3,4-(F) ₂ -Ph, 4-iPr-Ph, 4-Br-Ph], [1527!3,4-(F) ₂ -Ph, 4- iPr-Ph, 4-Me-Ph], [1528!3,4-(F) ₂ -Ph, 4-iPr-Ph, 4-iPr-Ph] , [1529!3,4-(F) ₂ -Ph, 4-iPr-Ph, 4-CF ₃ -Ph], [1530!3,4-(F) ₂ -

Ph, 4-iPr-Ph, 4 -MeO- Ph] , [1531 ! 3,4-(F) ₂ -Ph, 4-iPr-Ph, 4- Ph, Ph] , [1532 ".3,4-(F) ₂ -Ph, 4-iPr-Ph, 3,4-(Me) ₂ -Ph] , [1533

! 3,4-(F) ₂ -Ph, 4-iPr-Ph, 5-In] , [1534 ! 3,4-(F) ₂ -Ph, 4-CF ₃ - Ph, 2-Me-Ph] , [1535 ! 3,4-(F) ₂ -Ph, 4-CF ₃ -Ph, 3-F-Ph] , [1536

! 3,4-(F) ₂ -Ph, 4-CF ₃ -Ph, 3-Me-Ph] , [1537 ! 3,4-(F) ₂ -Ph, 4- CF ₃ -Ph, 4-F-Ph] , [1538 ! 3,4-(F) ₂ -Ph, 4-CF ₃ -Ph, 4-Cl-Ph] ,

[1539 ! 3,4-(F) ₂ -Ph, 4-CF ₃ -Ph, 4-Br-Ph] , [1540 ! 3,4-(F) ₂ -Ph, 4-CF ₃ -Ph, 4-Me-Ph] , [1541 ! 3,4-(F) ₂ -Ph, 4-CF ₃ -Ph, 4-iPr- Ph] , [1542 ! 3,4-(F) ₂ -Ph, 4-CF ₃ -Ph, 4-CF ₃ -Ph] , [1543 ! 3,4-

(F) ₂ -Ph, 4-CF ₃ -Ph, 4-MeO-Ph] , [1544 ! 3,4-(F) ₂ -Ph, 4-CF ₃ -Ph, 4-Ph, Ph] , [1545 ! 3,4-(F) ₂ -Ph, 4-CF ₃ -Ph, 3,4-(Me) ₂ -Ph] ,

[1546 ! 3,4-(F) ₂ -Ph, 4-CF ₃ -Ph, 5-In] , [1547 ! 3,4-(F) ₂ -Ph, 4- Ph, Ph, 2-Me-Ph] , [1548 ! 3,4-(F) ₂ -Ph, 4-Ph, Ph, 3-F-Ph] ,

[1549 ! 3,4-(F) ₂ -Ph, 4-Ph, Ph, 3-Me-Ph] , [1550 ! 3,4-(F) ₂ -Ph, 4-Ph, Ph, 4-F-Ph] , [1551 ! 3,4-(F) ₂ -Ph, 4-Ph, Ph, 4-Cl-Ph] ,

[1552 ! 3,4-(F) ₂ -Ph, 4-Ph, Ph, 4-Br-Ph] , [1553 ! 3,4-(F) ₂ -Ph, 4-Ph, Ph, 4-Me-Ph] , [1554 ! 3,4-(F) ₂ -Ph, 4-Ph, Ph, 4-iPr- Ph] , [1555 ! 3,4-(F) ₂ -Ph, 4-Ph, Ph, 4-CF ₃ -Ph] , [1556 ! 3,4-

(F) ₂ -Ph, 4-Ph, Ph, 4 -MeO-Ph] , [1557 ! 3,4-(F) ₂ -Ph, 4-Ph, Ph, 4-Ph, Ph] , [1558 ! 3,4-(F) ₂ -Ph, 4-Ph, Ph, 3,4-(Me) ₂ -Ph] ,

[1559 ! 3,4-(F) ₂ -Ph, 4-Ph, Ph, 5-In] , [1560 ! 3,4-(F) ₂ -Ph, 2,4-(F) ₂ -Ph, 2-Me-Ph] , [1561 ! 3,4-(F) ₂ -Ph, 2,4-(F) ₂ -Ph, 3- F-Ph] , [1562 ! 3,4-(F) ₂ -Ph, 2,4-(F) ₂ -Ph, 3-Me-Ph] , [1563 ! 3,4-(F) ₂ -Ph, 2,4-(F) ₂ -Ph, 4-F-Ph] , [1564 ! 3,4-(F) ₂ -Ph, 2,4-

(F) ₂ -Ph, 4-Cl-Ph] ₇ [1565 ! 3,4-(F) ₂ -Ph, 2,4-(F) ₂ -Ph, 4-Br-

Ph] , [1566 ! 3,4-(F) ₂ -Ph, 2,4-(F) ₂ -Ph, 4-Me-Ph] , [1567 ! 3,4- (F) ₂ -Ph, 2,4-(F) ₂ -Ph, 4-iPr-Ph] , [1568 ! 3,4-(F) ₂ -Ph, 2,4- (F) ₂ -Ph, 4-CF ₃ -Ph] , [1569 ! 3,4-(F) ₂ -Ph, 2,4-(F) ₂ -Ph, 4-MeO- Ph] , [1570 ! 3,4-(F) ₂ -Ph, 2,4-(F) ₂ -Ph, 4-Ph ₇ Ph] , [1571 ! 3,4-(F) ₂ -Ph, 2,4-(F) ₂ -Ph, 3,4-(Me) ₂ -Ph] , [1572 ! 3,4-(F) ₂ - Ph, 2,4-(F) ₂ -Ph, 5-In] , [1573 ! 3,4-(F) ₂ -Ph, 3,4-(Cl) ₂ -Ph, 2-Me-Ph] , [1574 ! 3,4-(F) ₂ -Ph, 3,4-(Cl) ₂ -Ph, 3-F-Ph] , [1575 ! 3,4-(F) ₂ -Ph, 3,4- (Cl) ₂ -Ph, 3-Me-Ph] , [1576 ^' .3,4-(F) ₂ -Ph, 3,4- (Cl) ₂ -Ph, 4-F-Ph] , [1577 ! 3,4-(F) ₂ -Ph, 3,4-(Cl) ₂ -Ph, 4- Cl-Ph] , [1578 ! 3,4-(F) ₂ -Ph, 3,4-(Cl) ₂ -Ph, 4-Br-Ph] , [1579 ! 3,4-(F) ₂ -Ph, 3,4- (Cl) ₂ -Ph, 4-Me-Ph] , [1580 ! 3,4-(F) ₂ -Ph, 3,4- (Cl) ₂ -Ph, 4-iPr-Ph] , [1581 ! 3,4-(F) ₂ -Ph, 3,4-(Cl) ₂ -Ph, 4-CF ₃ -Ph] , [1582 ! 3,4-(F) ₂ -Ph, 3,4-(Cl) ₂ -Ph, 4 -MeO- Ph] , [1583 ! 3,4-(F) ₂ -Ph, 3,4-(Cl) ₂ -Ph, 4-Ph, Ph] , [1584 ! 3,4- (F) ₂ -Ph, 3,4- (Cl) ₂ -Ph, 3,4-(Me) ₂ -Ph] , [1585 ! 3,4-(F) ₂ -Ph, 3,4- (Cl) ₂ -Ph, 5-In] , [1586 ! 3,4-(F) ₂ -Ph, 3,5-(Cl) ₂ -Ph, 2- Me-Ph] , [1587 ! 3,4-(F) ₂ -Ph, 3,5-(Cl) ₂ -Ph, 3-F-Ph] , [1588 ! 3,4-(F) ₂ -Ph, 3,5- (Cl) ₂ -Ph, 3-Me-Ph] , [1589 ! 3,4-(F) ₂ -Ph, 3,5- (Cl) ₂ -Ph, 4-F-Ph] , [1590 ! 3,4-(F) ₂ -Ph, 3,5-(Cl) ₂ -Ph, 4- Cl-Ph] , [1591 ! 3,4-(F) ₂ -Ph, 3,5-(Cl) ₂ -Ph, 4-Br-Ph] , [1592 ! 3,4-(F) ₂ -Ph, 3,5- (Cl) ₂ -Ph, 4-Me-Ph] , [1593 ! 3,4-(F) ₂ -Ph, 3,5- (Cl) ₂ -Ph, 4-iPr-Ph] , [1594 ! 3,4-(F) ₂ -Ph, 3,5-(Cl) ₂ -Ph, 4-CF ₃ -Ph], [1595 ! 3,4-(F) ₂ -Ph, 3,5-(Cl) ₂ -Ph, 4 -MeO-Ph] , [1596 ! 3,4-(F) ₂ -Ph, 3,5-(Cl) ₂ -Ph, 4-Ph, Ph] , [1597 ! 3,4- (F) ₂ -Ph, 3,5-(Cl) ₂ -Ph, 3,4-(Me) ₂ -Ph] , [1598 ! 3,4-(F) ₂ -Ph,

3,5- (Cl) ₂ -Ph, 5-In] , [1599 ! 3,4-(Cl) ₂ -Ph, Ph,, Ph] , [1600 ! 5- In,, Ph, Ph] „

[1601 : 5-In,, 2-F-Ph, 2-Me-Ph] , [1602 ! 5-In,, 2-F-Ph, 3-F-Ph] , [1603 ! 5-In, 2-F-Ph, 3-Me-Ph] , [1604 ! 5-In _λ 2-F-Ph, 4-F-Ph] , [1605 I 5 -In,, 2-F-Ph, 4-Cl-Ph] , [1606 ! 5-In _λ 2-F-Ph, 4-Br- Ph] , [1607 : 5 -In,, 2-F-Ph, 4-Me-Ph] , [1608 ! 5-In,, 2-F-Ph, 4- iPr-Ph] , [1609 ! 5-In _λ 2-F-Ph, 4-CF ₃ -Ph] , [1610 ! 5-In _N 2-F- Ph, 4-MeO-Ph] , [1611 ! 5-In _λ 2-F-Ph, 4-Ph, Ph] , [1612 ! 5-In _> 2-F-Ph, 3,4-(Me) ₂ -Ph] , [1613 ! 5-In, 2-F-Ph, 5-In] , [1614 ! 5- In, 3-CF ₃ -Ph, 2-Me-Ph] , [1615 ! 5-In, 3-CF ₃ -Ph, 3-F-Ph] ₇ [1616 ! 5-In, 3-CF ₃ -Ph, 3-Me-Ph] , [1617 ! 5-In, 3-CF ₃ -Ph, 4- F-Ph] , [1618 ! 5-In, 3-CF ₃ -Ph, 4-Cl-Ph] , [1619 ! 5-In, 3-CF ₃ - Ph, 4-Br-Ph] , [1620 ^' .5-In, 3-CF ₃ -Ph, 4-Me-Ph] , [1621 ! 5-In ₇ 3-CF ₃ -Ph, 4-iPr-Ph] , [1622. ^' 5-In, 3-CF ₃ -Ph, 4-CF ₃ -Ph] , [1623 ! 5-In, 3-CF ₃ -Ph, 4-MeO-Ph] , [1624 ! 5-In, 3-CF ₃ -Ph, 4- Ph, Ph] , [1625 ! 5-In, 3-CF ₃ -Ph, 3,4-(Me) ₂ -Ph] , [1626 ! 5-In, 3-CF ₃ -Ph, 5-In] , [1627 ! 5-In, 4-F-Ph, 2-Me-Ph] , [1628 ! 5- In ₇ 4-F-Ph, 3 -F-Ph] , [1629 ! 5-In ₇ 4-F-Ph, 3-Me-Ph] , [1630 ! 5-In, 4-F-Ph, 4-F-Ph] , [1631 ! 5-In, 4-F-Ph, 4-Cl-Ph] , [1632 ! 5-In ₇ 4-F-Ph ₇ 4-Br-Ph] , [1633 ! 5-In ₇ 4-F-Ph, 4-Me-Ph] , [1634 ! 5-In, 4-F-Ph, 4-iPr-Ph] , [1635 ! 5-In, 4-F-Ph, 4-CF ₃ - Ph] ₇ [1636 ! 5-In, 4-F-Ph ₇ 4 -MeO-Ph] , [1637 ! 5-In ₇ 4-F-Ph ₇ 4-Ph ₇ Ph] ₇ [1638 ! 5-In ₇ 4-F-Ph ₇ 3,4-(Me) ₂ -Ph] , [1639 ! 5-In, 4-F-Ph, 5-In] , [1640 ! 5-In ₇ 4-iPr-Ph, 2-Me-Ph] , [1641 ! 5- In ₇ 4-iPr-Ph, 3-F-Ph] ₇ [1642. ^' 5-In, 4-iPr-Ph, 3-Me-Ph] ,

[1643 I 5-In ₇ 4-iPr-Ph, 4-F-Ph] , [1644 ! 5-In ₇ 4-iPr-Ph, 4- Cl-Ph] , [1645 : 5-In, 4-iPr-Ph, 4-Br-Ph] , [1646 ! 5-In, 4- iPr-Ph, 4-Me-Ph] , [1647 ! 5-In, 4-iPr-Ph, 4-iPr-Ph] , [1648 ! 5-In, 4-iPr-Ph, 4-CF ₃ -Ph] , [1649 ! 5-In, 4-iPr-Ph, 4-MeO- Ph] , [1650 : 5-In, 4-iPr-Ph, 4-Ph, Ph] , [1651 ! 5-In, 4-iPr- Ph, 3,4-(Me) ₂ -Ph] , [1652 ^' .5-In, 4-iPr-Ph, 5-In] , [1653 ! 5- In, 4-CF ₃ -Ph, 2-Me-Ph] , [1654. ^' 5-In, 4-CF ₃ -Ph, 3-F-Ph] , [1655 ! 5-In, 4-CF ₃ -Ph, 3-Me-Ph] , [1656 ! 5-In, 4-CF ₃ -Ph, 4- F-Ph] , [1657 ! 5-In, 4-CF ₃ -Ph, 4 -Cl -Ph] , [1658 ! 5-In, 4-CF ₃ - Ph, 4-Br-Ph] , [1659 ! 5-In, 4-CF ₃ -Ph, 4-Me-Ph] , [1660 ! 5-In, 4-CF ₃ -Ph, 4-iPr-Ph] , [1661 ! 5-In, 4-CF ₃ -Ph, 4-CF ₃ -Ph] , [1662 ! 5-In, 4-CF ₃ -Ph, 4-MeO-Ph] , [1663 ! 5-In, 4-CF ₃ -Ph, 4- Ph, Ph] , [1664 ! 5-In, 4-CF ₃ -Ph, 3,4-(Me) ₂ -Ph] , [1665 ! 5-In, 4-CF ₃ -Ph, 5-In] , [1666 ! 5-In, 4-Ph, Ph, 2-Me-Ph] , [1667 ! 5- In, 4-Ph, Ph, 3-F-Ph] , [1668 ! 5-In, 4-Ph, Ph, 3-Me-Ph] , [1669 ! 5-In, 4-Ph, Ph, 4-F-Ph] , [1670 ! 5-In, 4-Ph, Ph, 4- Cl-Ph] , [1671 ! 5-In, 4-Ph, Ph, 4-Br-Ph] , [1672 ! 5-In, 4-Ph, Ph, 4-Me-Ph] , [1673 ! 5-In, 4-Ph, Ph, 4-iPr-Ph] , [1674.5- In, 4-Ph, Ph, 4-CF ₃ -Ph] , [1675 ! 5-In, 4-Ph, Ph, 4 -MeO-Ph] , [1676 ! 5-In, 4-Ph, Ph, 4-Ph, Ph] , [1677 ! 5-In, 4-Ph, Ph, 3,4-(Me) ₂ -Ph] , [1678 ! 5-In, 4-Ph, Ph, 5-In] , [1679 ! 5-In. 2,4-(F) ₂ -Ph, 2-Me-Ph] , [1680 ! 5-In. 2 , 4- (F) ₂ -Ph, 3-F-Ph] , [1681 ! 5-In. 2,4-(F) ₂ -Ph, 3-Me-Ph] , [1682 ! 5-In. 2,4- (F) ₂ - Ph, 4-F-Ph] , [1683 ! 5-In. 2,4-(F) ₂ -Ph, 4-Cl-Ph] , [1684 ! 5-In . 2,4-(F) ₂ -Ph, 4-Br-Ph] , [1685.' 5-In. 2,4-(F) ₂ -Ph, 4-Me-Ph] ,

[1686 : 5-Iru 2,4- (F) ₂ -Ph, 4-iPr-Ph] , [1687 ! 5-In^ 2,4- (F) ₂ - Ph, 4-CF ₃ -Ph] , [1688 I 5-Iru 2,4- (F) ₂ -Ph, 4 -MeO-Ph] , [1689 ! 5-In-. 2,4- (F) ₂ -Ph, 4-Ph, Ph] , [1690 ^' .5-In,, 2,4- (F) ₂ -Ph, 3,4- (Me) ₂ -Ph] , [1691 ! 5-In, 2,4- (F) ₂ -Ph, 5-In] , [1692 ! 5-In, 3,4- (Cl) ₂ -Ph, 2-Me-Ph] , [1693 ! 5-In, 3,4- (Cl) ₂ -Ph, 3-F-Ph] , [1694 ! 5-In, 3,4-(Cl) ₂ -Ph, 3-Me-Ph] , [1695 ! 5-In, 3,4- (Cl) ₂ -Ph, 4-F-Ph] , [1696 ! 5-In, 3,4- (Cl) ₂ -Ph, 4 -Cl -Ph] , [1697 ! 5-In, 3,4- (Cl) ₂ -Ph, 4-Br-Ph] , [1698 ! 5-In, 3,4- (Cl) ₂ -Ph, 4-Me-Ph] , [1699 ^' .5-In, 3,4- (Cl) ₂ -Ph, 4-iPr-Ph] , [1700 ! 5-In, 3,4- (Cl) ₂ -Ph, 4-CF ₃ -PhK

[1701 ! 5-In, 3,4- (Cl) ₂ -Ph, 4 -MeO-Ph] , [1702 ! 5-In, 3,4- (Cl) ₂ -Ph, 4-Ph, Ph] , [1703 ^' .5-In, 3,4- (Cl) ₂ -Ph, 3, 4- (Me) ₂ - Ph] , [1704 ! 5-In, 3,4- (Cl) ₂ -Ph, 5-In] , [1705 ! 5-In, 3,5- (Cl) ₂ -Ph, 2-Me-Ph] , [1706 ^' .5-In, 3,5-(Cl) ₂ -Ph, 3-F-Ph] , [1707 ^' .5-In, 3,5-(Cl) ₂ -Ph, 3-Me-Ph] , [1708 ! 5-In, 3,5- (Cl) ₂ -Ph, 4-F-Ph] ₇ [1709 ! 5-In, 3,5-(Cl) ₂ -Ph, 4-Cl-Ph] , [1710. ^' 5-In, 3,5- (Cl) ₂ -Ph, 4-Br-Ph] , [1711 ! 5-In, 3,5- (Cl) ₂ -Ph, 4-Me-Ph] , [1712 ! 5-In, 3,5-(Cl) ₂ -Ph, 4-iPr-Ph] , [1713 ! 5-In, 3,5-(Cl) ₂ -Ph, 4-CF ₃ -Ph] , [1714 ! 5-In, 3,5- (Cl) ₂ -Ph, 4 -MeO- Ph] , [1715 ! 5-In, 3,5-(Cl) ₂ -Ph, 4-Ph, Ph] , [1716 ! 5-In, 3,5-(Cl) ₂ -Ph, 3,4-(Me) ₂ -Ph] , [1717 ! 5-In, 3,5- (Cl) ₂ -Ph, 5-In] , [1718 ! 2-Np, Ph, Ph] , [1719 ! 1-Np, Ph, Ph] , [1720 ! l-Np _λ 2-F-Ph, 2-Me-Ph] , [1721 I 1-Np _> 2-F-Ph, 3- F-Ph] , [1722 ! l-Np _N 2-F-Ph, 3-Me-Ph] , [1723 ! 1-Np _> 2-F-Ph, 4-F-Ph] , [1724 ! l-Np _N 2-F-Ph, 4-Cl-Ph] , [1725 ! 1-Np> 2-F-Ph,

4-Br-Ph] , [1726 ^' .1-Np _> 2-F-Ph, 4-Me-Ph] , [1727 ! 1-Np _^ 2-F- Ph, 4-iPr-Ph] , [1728 ! 1-Np _^ 2-F-Ph, 4-CF ₃ -Ph] , [1729 ! 1-Np^ 2-F-Ph, 4-MeO-Ph] , [1730.1-Np,, 2-F-Ph, 4-Ph, Ph] , [1731 '.1- Np _λ 2-F-Ph, 3,4-(Me) ₂ -Ph] , [1732 ! 1-Np^ 2-F-Ph, 5-In] , [1733

: l-Np _λ 3-CF ₃ -Ph, 2-Me-Ph] , [1734.1-Np,, 3-CF ₃ -Ph, 3-F-Ph] ,

[1735 : 1-Npϊ 3-CF ₃ -Ph, 3-Me-Ph] , [1736 '.1-Np _^ 3-CF ₃ -Ph, 4-F- Ph] , [1737 ! 1-Np _^ 3-CF ₃ -Ph, 4-Cl-Ph] , [1738 ! 1-Np^ 3-CF ₃ -Ph, 4-Br-Ph] , [1739 : l-Np _λ 3-CF ₃ -Ph, 4-Me-Ph] , [1740 ! 1-Np^ 3- CF ₃ -Ph, 4-iPr-Ph] , [1741 : 1-Np,. 3-CF ₃ -Ph, 4-CF ₃ -Ph] , [1742 ! 1-Np,, 3-CF ₃ -Ph, 4-MeO-Ph] , [1743 ! 1-Np _^ 3-CF ₃ -Ph, 4-Ph ₇ Ph] ,

[1744 I l-Np _λ 3-CF ₃ -Ph, 3,4-(Me) ₂ -Ph] , [1745 ! 1-Np^ 3-CF ₃ -Ph, 5-In] , [1746 ^' .1-Np, 4-F-Ph, 2-Me-Ph] , [1747 ^' .1-Np, 4-F-Ph, 3 -F-Ph] , [1748 : 1-Np, 4-F-Ph, 3-Me-Ph] , [1749 '.1-Np, 4-F- Ph, 4-F-Ph] , [1750 ^' .1-Np, 4-F-Ph ₇ 4-Cl-Ph] , [1751 ^' .1-Np ₇ 4- F-Ph, 4-Br-Ph] , [1752.1-Np, 4-F-Ph, 4-Me-Ph] , [1753 ^' .1-Np ₇ 4-F-Ph ₇ 4-iPr-Ph] , [1754 ! 1-Np, 4-F-Ph, 4-CF ₃ -Ph] , [1755 ! 1-Np, 4-F-Ph, 4-MeO-Ph] , [1756. ^' 1-Np, 4-F-Ph, 4-Ph, Ph] ,

[1757 ^" .1-Np, 4-F-Ph, 3,4-(Me) ₂ -Ph] ₇ [1758 I 1-Np, 4-F-Ph, 5- In] , [1759 : 1-Np, 4-iPr-Ph, 2-Me-Ph] , [1760 ^' .1-Np, 4-iPr- Ph, 3-F-Ph] , [1761 ^' .1-Np, 4-iPr-Ph, 3-Me-Ph] , [1762.1-Np, 4-iPr-Ph, 4-F-Ph] , [1763 ^" .1-Np, 4-iPr-Ph, 4-Cl-Ph] , [1764 i 1-Np, 4-iPr-Ph, 4-Br-Ph] , [1765 '.1-Np ₇ 4-iPr-Ph, 4-Me-Ph] ,

[1766 : 1-Np, 4-iPr-Ph, 4-iPr-Ph] , [1767 ^' .1-Np, 4-iPr-Ph, 4- CF ₃ -Ph] ₇ [1768 : 1-Np, 4-iPr-Ph, 4 -MeO-Ph] , [1769 ! 1-Np, 4- iPr-Ph, 4-Ph, Ph] , [1770 '.1-Np, 4-iPr-Ph, 3,4-(Me) ₂ -Ph] ₇

[1771 : 1-Np, 4-iPr-Ph, 5-In] , [1772 ! 1-Np ₇ 4-CF ₃ -Ph, 2-Me- Ph] , [1773 ! 1-Np, 4-CF ₃ -Ph, 3-F-Ph] , [177411-Np, 4-CF ₃ -Ph, 3-Me-Ph] , [1775 ! 1-Np, 4-CF ₃ -Ph, 4-F-Ph] , [1776 ! 1-Np, 4- CF ₃ -Ph, 4-Cl-Ph] , [1777 ! 1-Np, 4-CF ₃ -Ph, 4-Br-Ph] , [1778 ! 1-Np, 4-CF ₃ -Ph, 4-Me-Ph] , [1779 ! 1-Np, 4-CF ₃ -Ph, 4-iPr-Ph] , [1780 ! 1-Np, 4-CF ₃ -Ph, 4-CF ₃ -Ph] , [1781 ! 1-Np, 4-CF ₃ -Ph, 4- MeO-Ph] , [1782 ! 1-Np, 4-CF ₃ -Ph, 4-Ph, Ph] , [1783 ! 1-Np, 4- CF ₃ -Ph, 3,4-(Me) ₂ -Ph] , [1784 ! 1-Np, 4-CF ₃ -Ph, 5-In] , [1785 ! 1-Np, 4-Ph, Ph, 2-Me-Ph] , [1786 ! 1-Np, 4-Ph, Ph, 3-F-Ph] , [1787 ! 1-Np, 4-Ph, Ph, 3-Me-Ph] , [1788 ! 1-Np, 4-Ph, Ph, 4- F-Ph] , [1789 ! 1-Np, 4-Ph, Ph, 4-Cl-Ph] , [1790 ! 1-Np, 4-Ph, Ph, 4-Br-Ph] , [1791 ! 1-Np, 4-Ph, Ph, 4-Me-Ph] , [1792 ! 1-Np, 4-Ph, Ph, 4-iPr-Ph] , [1793 ! 1-Np, 4-Ph, Ph, 4-CF ₃ -Ph] , [1794 ! 1-Np, 4-Ph, Ph, 4-MeO-Ph] , [1795 ! 1-Np, 4-Ph, Ph, 4- Ph, Ph] , [1796 ! 1-Np, 4-Ph, Ph, 3,4-(Me) ₂ -Ph] , [1797 ! 1-Np, 4-Ph, Ph, 5-In] , [1798 ! 1-Np, 2,4-(F) ₂ -Ph, 2-Me-Ph] , [1799 ! 1-Np, 2,4-(F) ₂ -Ph, 3-F-Ph] , [1800 ! 1-Np, 2,4-(F) ₂ -Ph, 3-Me- Ph],

[1801 ! 1-Np, 2,4-(F) ₂ -Ph, 4-F-Ph] , [1802 ! 1-Np, 2,4-(F) ₂ -Ph, 4-Cl-Ph] , [1803 ! 1-Np, 2,4-(F) ₂ -Ph, 4-Br-Ph] , [1804 ! 1-Np, 2,4-(F) ₂ -Ph, 4-Me-Ph] , [1805 ! 1-Np, 2 , 4- (F) ₂ -Ph, 4-iPr-Ph] , [1806 ! 1-Np, 2,4-(F) ₂ -Ph, 4-CF ₃ -Ph] , [1807 ! 1-Np, 2,4- (F) ₂ - Ph, 4 -MeO-Ph] , [1808 ! 1-Np, 2,4-(F) ₂ -Ph, 4-Ph, Ph] , [1809 ! 1-Np, 2,4- (F) ₂ -Ph, 3,4-(Me) ₂ -Ph] , [1810 ! 1-Np, 2 , 4- (F) ₂ -Ph, 5-In] , [1811 ! 1-Np, 3,4- (Cl) ₂ -Ph, 2-Me-Ph] , [1812 ! 1-Np,

3,4- (Cl) ₂ -Ph, 3-F-Ph] , [1813.1-Np> 3 ,4- (Cl) ₂ -Ph, 3-Me-Ph] , [1814 I 1-Np _> 3,4- (Cl) ₂ -Ph, 4-F-Ph] , [1815. l-Np _N 3,4- (Cl) ₂ - Ph, 4-Cl-Ph] , [1816 I 1-Np, 3,4- (Cl) ₂ -Ph, 4-Br-Ph] , [1817 ^* .1- Np _> 3,4- (Cl) ₂ -Ph, 4-Me-Ph] , [1818 I 1-Np^ 3,4-(Cl) ₂ -Ph, 4- iPr-Ph] , [1819 : 1-Np^ 3,4- (Cl) ₂ -Ph, 4-CF ₃ -Ph] , [182O i I-Np^ 3,4- (Cl) ₂ -Ph, 4-MeO-Ph] , [1821 I 1-Np^ 3,4-(Cl) ₂ -Ph, 4-Ph, Ph] , [1822 : 1-Np _> 3,4- (Cl) ₂ -Ph, 3,4-(Me) ₂ -Ph] , [1823 ! 1-Np^ 3,4- (Cl) ₂ -Ph, 5-In] , [1824 ^' .1-Np, 3,5-(Cl) ₂ -Ph, 2-Me-Ph] , [1825 ! 1-Np^ 3,5- (Cl) ₂ -Ph, 3-F-Ph] , [1826 ! 1-Np _^ 3,5- (Cl) ₂ - Ph, 3-Me-Ph] , [1827 ! 1-Np^ 3,5-(Cl) ₂ -Ph, 4-F-Ph] , [1828 ! 1- Np _^ 3,5- (Cl) ₂ -Ph, 4-Cl-Ph] , [1829 ! 1-Np _^ 3,5-(Cl) ₂ -Ph, 4-Br- Ph] , [1830 : 1-Np _> 3,5- (Cl) ₂ -Ph, 4-Me-Ph] , [1831 : 1-Np _> 3,5- (Cl) ₂ -Ph, 4-iPr-Ph] , [1832 ! 1-Np^ 3,5-(Cl) ₂ -Ph, 4-CF ₃ -Ph] , [1833 ! 1-Np _^ 3,5- (Cl) ₂ -Ph, 4-MeO-Ph] , [1834 ^' . l-Np _^ 3,5- (Cl) ₂ -Ph, 4-Ph, Ph] , [1835 ".1-Np^ 3,5-(Cl) ₂ -Ph, 3,4- (Me) ₂ - Ph] , [1836 ! 1-Np _^ 3,5-(Cl) ₂ -Ph, 5-In] , [1837 ! 3 -Me-2-Np, Ph, Ph] ₀

In the above-described examples, for example "4 -CN-Ph" means a 4 - cyanophenyl group, "1-Np" means a 1-naphthyl group, "3-Me-2-Np" means a 3-methyl-2-naphthyl group, further, (Ia-29) and (Ia-1835) mean the following compounds, respectively.

Next, production examples of raw material compounds for compounds of the present invention will be shown.

Reference Production Example 1

(IV-I) Production of N- [1- (4-trifluoromethylphenyl) -3- trimethylsilyl-2-propinylidene) -2-methylaniline

To a toluene solution (10 mL) of 2 '-methyl-4- trifluoromethylbenzanilide (2.6 g) was added phosphorus pentachloride (1.93 g) at room temperature, and the mixture was stirred at the same temperature for 1 hour, further at 60°C for 1.5 hours. The reaction mixture was concentrated to obtain N- (2-methylphenyl) -4-trifluoromethylbenzimidoyl chloride.

Next, to a triethylamine solution (25 mL) of

trimethylsilylacetylene (0.91 g) was added palladium (II) acetate (11 mg) , triphenylphosphine (22 mg) and N- (2- methylphenyl) -4-trifluoromethylbenzimidoyl chloride, sequentially, and the mixture was stirred at 60 ⁰ C for 30 minutes and at 80°C for 1.5 hours. The reaction mixture was cooled, then, tert-butyl methyl ether (30 mL) was added, and the generated insoluble materials were filtrated, and the filtrate was concentrated under reduced pressure condition. The resultant residue was subjected to silica gel column chromatography (hexane : ethyl acetate = 30:1) to obtain N- [1- (4-trifluoromethylphenyl) -3- trimethylsilyl-2-propinylidene] 2-methylaniline (1.8 g) as a yellow oil.

¹ H-NMR (CDCl ₃ ) δ (ppm) : 0.11 (9H, s) , 2.20 (3H, s) , 6.99 (IH, d, J = 8.2 Hz), 7.05 to 7.24 (4H, m) , 7.72 (2H, d, J = 8.9 Hz), 8.30 (2H, d, J = 8.9 Hz)

Reference Production Examples 2 to 92

The following compounds were synthesized in the same manner as in Reference Production Example 1.

(IV-2) N- [l- (2-methylphenyl) -3-trimethylsilyl-2- propinylidene] aniline

¹ H-NMR(CDCl ₃ )δ (ppm) :0.07(9H,s) ,2.62 (3H,s) ,7.09~ 7.40(8H,m) , 7.75~7.80 (IH,m)

(IV-3) N- Cl- (3-methylphenyl) -3-trimethylsilyl-2-

propinylidene] aniline

¹ H-NMR(CDCl ₃ ) δ (ppm) : 0.12 (9H, s) , 2.34 (3H, s) , 7.06 — 7.33 (7H, m) , 7.93 — 8.01(2H, m)

(IV-4) N- Cl- (4-methylphenyl) -3-trimethylsilyl-2- propinylidene] aniline

¹ H-NMR(CDCl ₃ ) δ (ppm) :0.12(9H,s),2.42(3H,s),7.07~7.39(7H,m), 8.04 — 8.09 (2H,m)

(IV-5) N- [l- (3-methoxyphenyl) -3-trimethylsilyl-2- propinylidene] aniline

¹ H-NMR(CDCl ₃ ) δ (ppm) : 0.12 (9H, s) , 3.89 (3H, s) , 6.94 —7.39 (7H,m) , 8.10 — 8.16 (2H,m)

(IV-6) N- Cl- (4-methoxyphenyl) -3-trimethylsilyl-2- propinylidene] aniline

¹ H-NMR(CDCl ₃ )δ(ppm) : 0.08 (9H, s) , 4.05 (3H, s) , 6.68 ~7.48 (7H,m) , 7.56—7.62 (2H,m)

(IV-7) N- Cl- (2-chlorophenyl) -3-trimethylsilyl-2- propinylidene] aniline

¹ H-NMR(CDCl ₃ ) δ (ppm) : 0.13 (9H,s) , 7.06~7.48 (7H,m) , 8.01— 8.18 (2H,m)

(IV-8) N- Cl- (4-trifluoromethylphenyl) -3-trimethylsilyl-2- propinylidene] aniline

¹ H-NMR(CDCl ₃ )δ(ppm) : 0.15 (9H, s) , 7.10~7.45 (5H,m) , 7.62 (2H,d, J=8.2Hz) , 8.40 (2H, d, J=8.2Hz)

(IV- 9) N- Cl- (4-nitrophenyl) -3-trimethylsilyl-2- propinylidene] aniline

¹ H-NMR(CDCl ₃ )δ(ppm) : 0.17 (9H, s) , 7.19~7.47 (7H,m) , 8.27— 8.40 (2H,m)

(IV-IO) N- [l- (4-phenylphenyl) ~3~trimethylsilyl-2- propinylidene] aniline

¹ H-NMR(CDCl ₃ )δ(ppm) :0.14 (9H,s) , 7.10—7.65 (12H,m) , 8.21~ 8.27 (2H,m)

(IV-Il) N- Cl- (4-trifluoromethylphenyl) -3-trimethylsilyl-2- propinylidene] -4-chloroaniline

¹ H-NMR(CDCl ₃ )δ (ppm) :0.18 (9H,s) , 7.11 (2H, d, J=8.7Hz) , 7.35 (2H,d,J=8.7Hz) ,7.72 (2H, d, J=8.2Hz) ,8.27 (2H, d, J=8.2Hz)

(IV- 12) N- Cl- (4-trifluoromethylphenyl) -3-trimethylsilyl-2- propinylidene] -4-methylaniline

¹ H-NMR(CDCl ₃ ) δ(ppm) :0.18 (9H,s) ,2.38 (3H,s) ,7.17 (4H,dd, J=8.4Hz) ,7.70 (2H,d, J=8.3Hz) ,8.27 (2H, d, J=8. OHz)

(IV-13) N- Cl- (4-trifluoromethylphenyl) -3-trimethylsilyl-2- propinylidene] -4-bromoaniline

¹ H-NMR(CDCl ₃ )δ(ppm) :0.18(9H,s),7.05 (2H, d, J=8.8Hz) , 7.50 (2H,d, J=8.8Hz) ,7.72 (2H, d, J=8.3Hz) , 8.27 (2H, d, J=8. OHz)

(IV- 14) N- Cl- (4-trifluoromethylphenyl) -3-trimethylsilyl-2- propinylidene] -3-methylaniline

¹ H-NMR(CDCl ₃ )O(PPm) : 0.16 (9H, s) , 2.38 (3H, s) , 6.96 — 7.02 (3H,m) , 7.27 ( IH, d,J=8. IHz) , 7.71 (2H, d, J=8.2Hz) ,8.28 (2H, d, J=8. OHz)

(IV- 15) N- Cl- (4-trifluoromethylphenyl) ~3-trimethylsilyl-2- propinylidene] -3-chloroaniline 1H-NMR(CDCl ₃ )δ(ppm) :0.18 (9H,s) , 7.01 (IH, d, J=7.8Hz) ,7.17—

7.19 (2H,m) ,7.32 (IH, t , J=7.8Hz) ,7.72 (2H, d, J=8.3Hz) ,8.27 (2H,d,

J=8.0Hz)

(IV-16) N- [l- (4-trifluoromethylphenyl) -3 -trimethylsilyl-2 - propinylidene] -4-phenylaniline

¹ H-NMR(CDCl ₃ ) δ (ppm) :0.17(9H,s) ,7.28 (2H, d, J=8.7Hz) , 7.35 (IH, t, J=7.4Hz) ,7.46 (2H, t , J=7.6Hz) ,7.63 (4H, d, J=8.5Hz) ,7. 73 (2H,d, J=8.2Hz) ,8.30 (2H, d, J=8.2Hz)

(IV-17) N- Cl- (4-trifluoromethylphenyl) -3 -trimethylsilyl-2 - propinyIidene] -4-isopropylaniline

¹ H-NMR(CDCl ₃ )δ(ppm) : 0.16 (9H, s) , 1.26 (3H, s) , 1.28 (3H, s) .2.90~ 2.97 (IH.m) .7.14 (2H, d, J=8.3Hz) ,7.24 (2H, d, J=8. OHz) ,7.71(2H,d, J=8.3Hz) ,8.28 (2H,d, J=8.0Hz)

(IV-18) N- Cl- (4-trifluoromethylphenyl) -3-trimethylsilyl-2- propinylidene) -4-trifluoromethylaniline 1H-NMR(CDCl ₃ ) δ (ppm) : 0.12 (9H,s) ,7.14 (2H, d, J=8.2Hz) , 7.64 (2H,d, J=8.5Hz) ,7.74 (2H, d, J=8.2Hz) ,8.28 (2H, d, J=8. OHz) (IV-19) N- Cl- (4-trifluoromethylphenyl) -3-trimethylsilyl-2- propinylidene) -4-fluoroaniline

¹ H-NMR(CDCl ₃ ) δ (ppm) :0.19(9H,s) ,7.08 (2H, d, J=8.6Hz) , 7.17~ 7.21 (2H,m) ,7.72 (2H, d, J=8.5Hz) ,8.28 (2H, d, J=8.5Hz)

(IV-20) N- [l- (4-trifluoromethylphenyl) -3-trimethylsilyl-2- propinylidene] -3 -fluoroaniline

¹ H-NMR(CDCl ₃ )δ(ppm) : 0.16 (9H, s) , 6.87—6.91 (3H,m) , 7.30~ 7.36 (IH, m) ,7.72 (2H, d, J=8.2Hz) ,8.27 (2H, d, J=8. OHz) (IV-21) N- Cl- (4-trifluoromethylphenyl) -3 -trimethylsilyl-2-

propinylidene] -3 , 4-dimethylaniline

¹ H-NMR(CDCl ₃ ) δ(ppm) :0.19(9H,s) , 2.29(6H,s), 7.03(lH,d, J=8.0Hz) , 7.08 (IH, s) ,7.14 (IH, d, J=7.7Hz) ,7.70 (2H, d, J=8.2Hz) , 8.27 (2H,d, J=8.2Hz)

(IV- 22) N- Cl- (4-trifluoromethylphenyl) -3-trimethylsilyl-2- propinylidene) -4-methoxyaniline 1H-NMR(CDCl ₃ ) δ (ppm) : 0.22 (9H, s) , 3.85 (3H, s) ,

6.93 (2H,d,J=8.7Hz) , 7.34 (2H, d, J=8.9Hz) , 7.70 (2H, d, J=8.5Hz) , 8.27 (2H,d, J=8.2Hz)

(IV-23) N- Cl- (4-trifluoromethylphenyl) -3-trimethylsilyl-2- propinylidene] -2-methylaniline 1H-NMR(CDCl ₃ ) δ (ppm) : 0.11 (9H,s) , 2.20(3H,s), 6.99 (IH, d, J=8.2Hz) , 7.05 ~7.24 (3H, m) , 7.72 (2H, d, J=8.9Hz) , 8.30 (2H,d, J=8.9Hz)

(IV-24) N- Cl- (4-trifluoromethylphenyl) -3-trimethylsilyl-2- propinylidene] -3 , 4-trimethyleneaniline 1H-NMR(CDCl ₃ )δ(ppm) :0.19 (9H ₁ a) , 2.08~2.15 (2H,m) , 2.74 (4H,t,J=7.3Hz) , 7.03 (IH, d, J=8. OHz) , 7.17 (IH, s), 7.23 ( IH, d, J=8. OHz) ,7.70 (2H, d, J=8. OHz) ,8.28 (2H, d, J=8.3Hz) (IV-25) N- Cl- (2-methylphenyl) -3-trimethylsilyl-2- propinylidene] -4-methylaniline

¹ H-NMR(CDCl ₃ ) δ(ppm) : 0.10 (9H, s) , 2.36 (3H, s) , 2.60 (3H, s) , 7.10 (2H,d, J=8.3Hz) , 7.17 (2H, d, J=8. OHz) ,7.22 — 7.31 (3H,m) ,7.74 (IH, d, J=7.3Hz) (IV-26) N- Cl- (2-chlorophenyl) -3-trimethylsilyl-2-

propinylidene] -4-methylaniline

¹ H-NMR(CDCl ₃ ) δ (ppm) :0.11(9H,s) ,2.37 (3H,s) ,7.18 (4H,s) ,7.33

—7.35 (2H,m) ,7.42—7.45(lH,m) ,7.66— 7.68 ( IH, m)

(IV-27) N- [l- (2,4-dichlorophenyl) -3-trimethylsilyl-2- propinylidene] -4-methylaniline

¹ H-NMR(CDCl ₃ ) δ(ppm) : 0.12 (9H, s) , 2.37 (3H, s) , 7.18 (4H, s) , 7.31—

7.46 (2H,m) ,7.63 (IH, d, J=8.2Hz)

(IV-28) N- [l- (3-chlorophenyl) -3-trimethylsilyl-2- propinylidene] -4-methylaniline

¹ H-NMR(CDCl ₃ ) δ (ppm) : 0.17 (9H,s) , 2.37(3H,s),

7.11 (2H,d, J=8.3Hz) , 7.17 (2H ₇ d, J=8. OHz) ,7.37 (IH, t , J=7.8Hz) ,

7.43 (IH, d, J=8.0Hz) ,8.04 (IH, d, J=7.6Hz) 8.16 (IH, s) (IV-29) N- [l- (2,4-dimethylphenyl) -3-trimethylsilyl-2- propinylidene] -4-methylaniline

¹ H-NMR(CDCl ₃ ) δ(ppm) : 0.09 (9H, s) , 2.35 (3H, s) , 2.36 (3H, s) ,

2.57 (3H,s) , 7.05—7.08 (4H,m) ,7.16 (2H, d, J=8. OHz) , 7.67(lH,d, J=7.7Hz)

(IV-30) N- Cl- (2 -fluorophenyl) -3-trimethylsilyl-2- propinylidene] -4-methylaniline

¹ H-NMR(CDCl ₃ ) δ (ppm) :0.12(9H,s) ,2.37 (3H,s) ,7.10~ 7.21(6H,m), 7.39—7.44 (IH, m) , 7.91 (IH, t , J=7.8Hz)

(IV-31) N- Cl- (4 -fluorophenyl) -3-trimethylsilyl-2- propinylidene] -4-methylaniline

¹ H-NMR(CDCl ₃ ) δ(ppm) :0.16 (9H,s), 2.37 (3H,s), 7.07— 7.18 (6H,m) , 8.15— 8.19 (2H,m)

(IV-32) N- [l- (2, 4-difluorophenyl) -3-trimethylsilyl-2- propinylidene] -4-methylaniline

¹ H-NMR(CDCl ₃ ) δ(ppm) : 0.12 (9H, s) , 2.36 (3H, s) , 6.84 ~ 6.97 (2H,m) ,7.10 (2H, d, J=8.2Hz) ,7.17 (2H, d, J=8.5Hz) ,7.92— 7.98 (IH, m)

(IV-33) N- [l- (4-isopropylphenyl) -3-trimethylsilyl-2- propinylidene] -4-methylaniline 1H-NMR(CDCl ₃ ) δ (ppm) : 0.15 (9H, s) , 1.27 (3H, s) , 1.29 (3H, s) ,

2.36 (3H, s) ,2.94 —3.01 (IH, m) ,7.08 (2H, d, J=8.2Hz) ,

7.16 (2H,d, J=8.2Hz) , 7.31 (2H, d, J=8.2Hz) ,8.09 (2H, d, J=8.5Hz)

(IV-34) N- [l- (3,4-dichlorophenyl) -3-trimethylsilyl-2- propinylidene) -4-methylaniline 1H-NMR(CDCl ₃ ) δ (ppm) : 0.18(9H,s), 2.37(3H,s),

7.12 (2H,d,J=8.3Hz) , 7.18 (2H, d, J=8.3Hz) , 7.51 (IH, d, J=8.5Hz) , 7.97—8.26 (2H,m)

(IV-35) N- Cl- (3, 4 -difluorophenyl) -3-trimethylsilyl-2- propinylidenej -4-methylaniline 1H-NMR(CDCl ₃ ) δ(ppm) :0.17(9H,s) , 2.37(3H,s),

7.10(2H,d, J=8.2Hz) , 7.17 (2H, d, J=8.2Hz) , 7.22 (IH, d, J=8. OHz) , 7.90—8.04 (2H,m)

(IV-36) N- Cl- (2,3-dichlorophenyl) -3-trimethylsilyl-2- propinylidene] -4-methylaniline

¹ H-NMR(CDCl ₃ ) δ(ppm): 0.12 (9H,s), 2.37(3H,s), 7.19(4H,m), 7.28 (IH, t, J=7.8Hz) , 7.51—7.55 (2H,m)

(IV-37) N- Cl- (3,5-dichlorophenyl) -3-trimethylsilyl-2-

propinylidene] -4-methylaniline

¹ H-NMR(CDCl ₃ )O(PPm) : 0.19(9H,s), 2.37(3H,s), 7.13(2H,d, J=8.3Hz), 7.18 (2H,d,J=8.5Hz) , 7.44 (IH, d, J=82. OHz) , 8.04 (2H,d, J=2.0Hz)

(IV-38) N- [l- (3, 5-difluorophenyl) -3-trimethylsilyl-2 - propinylidene] -4-methylaniline

¹ H-NMR(CDCl ₃ )O(PPm) : 0.18(9H,s), 2.37(3H,s), 6.87~ 6.93 (IH, m) , 7.14 (2H, d, J=8.5Hz) ,7.18 (2H, d, J=8.5Hz) , 7.70 (2H,d, J=8.5Hz)

(IV-39) N- [l- (3,5-dimethylphenyl) -3-trimethylsilyl-2- propinylidene] -4-methylaniline

¹ H-NMR(CDCl ₃ )δ(ppm) : 0.15 (9H, s) , 2.36 (3H, s) , 2.39 (6H, s) , 7.06 (2H,d, J=8.2Hz) , 7.11 (IH, s) , 7.16 (2H, d, J=8.5Hz) , 7.78 (2H,s)

(IV-40) N- [l- (3,4-dimethylphenyl) -3-trimethylsilyl-2- propinylidene] -4-methylaniline

¹ H-NMR(CDCl ₃ )δ(ppm) : 0.14 (9H, s) , 2.31 (3H, s) , 2.32 (3H, s) , 2.35 (3H,s) ,7.06 (2H, d, J=8.5Hz) , 7.15 (2H, d, J=8.5Hz) ,7.20 (IH, d, J=8.0Hz) ,7.87 (IH, d, J=7.8Hz) ,7.94 (IH, s) (IV-41) N- [l- (4-methylphenyl) -3-trimethylsilyl-2- propinylidene] -4-methylaniline

¹ H-NMR(CDCl ₃ )δ(ppm) : 0.14 (9H, s) , 2.35 (3H, s) , 2.40 (3H, s) , 7.07(2H,d, J=8.3Hz) , 7.15 (2H, d, J=8.5Hz) ,7.24 (2H, d, J=8.5Hz) ,8. 05 (2H,d, J=8.0Hz) (IV-42) N- Cl- (4-chlorophenyl) -3-trimethylsilyl-2-

propinylidene] -4-methylaniline 1H-NMR(CDCl ₃ )δ(ppm) : 0.16 (9H, s) , 2.36 (3H, s) ,

7.10 (2H,d, J=8.3Hz) , 7.17 (2H, d, J=8. OHz) ,7.41 (2H, d, J=8.5Hz) , 8.10 (2H,d, J=8.5Hz)

(IV-43) N- [l- (3-trifluoromethylphenyl) -3-trimethylsilyl-2- propinylidene] -4-methylaniline 1H-NMR(CDCl ₃ ) δ(ppm) :0.19 (9H,s) , 2.38(3H,s),

7.15 (2H,d,J=8.5Hz) , 7.19 (2H, d, J=8.5Hz) , 7.57 (IH, t , J=7.8Hz) , 7.72 (IH, d, J=8.5Hz) ,8.35 (IH, d, J=8. OHz) , 8.46 (IH, S) (IV-44) N- [l- (2, 6-difluorophenyl) -3-trimethylsilyl-2- propinylidene) -4-methylaniline 1H-NMR(CDCl ₃ ) δ (ppm) : 0.12 (9H,s) ,2.38 (3H,s) , 6.97 (2H,t,J=7.8Hz) ,7.20 (4H,s) , 7.31~7.38 ( IH, m) (IV-45) N- Cl- (4-trifluoromethylphenyl) -3-trimethylsilyl-2- propinylidene) -2-chloroaniline

¹ H-NNR(CDCl ₃ ) δ (ppm) : 0.12 (9H,s) , 7.04-7.15 (2H,m) , 7.24- 7.40(lH,m), 7.44-7.47 (IH, m) , 7.74 (2H, d, J=8.2Hz) , 8.33 (2H,d, J=8.2Hz) ,

(IV-46) N- Cl- (4-trifluoromethylphenyl) -3-trimethylsilyl-2- propinylidene] -2-fluoroaniline

¹ H-NNR(CDCl ₃ ) δ (ppm) : 0.13 (9H,s) ,7.07-7.16 (4H,m) , 7.72 (2H,d, J=8.1Hz) , 8.31 (2H,d, J=8. IHz) ,

(IV-47) N- Cl- (2-trifluoromethylphenyl) -3-trimethylsilyl-2- propinylidene] -4-methylaniline 1H-NNR(CDCl ₃ ) δ(ppm) :0.11(9H,s) , 7.15-7.21 (4H, m) , 7.49-

7 . 77 (4H, m)

(IV-48) N- [l- (4-trifluoromethoxyphenyl) -3-trimethylsilyl- 2-propinylidene] -4-methylaniline

¹ H-NNR(CDCl ₃ ) δ(ppm) : 0.17 (9H, s) , 2.37 (3H, s) , 7.08-7.32 (6H,m) , 8.21 (2H,d, J=8.4Hz)

(IV-49) N- [l- (4-cyanophenyl) -3-trimethylsilyl-2- propinylidene] -4-methylaniline

¹ H-NNR(CDCl ₃ ) δ (ppm) : 0.19 (9H,s) ,2.30 (3H,s) , 7.13-7.22 (4H,m) , 7.73 (2H,d, J=8.2Hz) ,8.27 (2H, d, J=8.2Hz) (IV-50) N- [l- (4-bromophenyl) -3-trimethylsilyl-2- propinylidene] -4-methylaniline

¹ H-NNR(CDCl ₃ ) δ (ppm) :0.17(9H,s),2.37(3H,s),7.08-7.20(4H,m), 7.58 (2H,d, J=8.7Hz) ,8.04 (2H, d, J=8.7Hz) (IV-51) N- [l- (3-bromophenyl) -3-trimethylsilyl-2- propinylidene] -4-methylaniline

¹ H-NNR(CDCl ₃ ) δ(ppm) : 0.18 (9H, s) , 2.37 (3H, s) , 7.10-7.30 (5H,m) , 7.56-7.62 (IH, m) , 8.06-8.15 (IH, m) , 8.31-8.35 (IH, m) (IV-52) N- [l- (2-bromophenyl) -3-trimethylsilyl-2- propinylidene] -4-methylaniline

¹ H-NNR(CDCl ₃ ) δ (ppm) : 0.12 (9H,s), 2.37(3H,s), 7.24- 7.29(5H,m), 7.35-7.41 (IH, m) , 7.64 (2H, d, J=7.5Hz) (IV-53) N- [l- (2-methylphenyl) -3-trimethylsilyl-2- propinylidene] -3-methylaniline

¹ H-NNR(CDCl ₃ ) δ(ppm): 0.08 (9H, s) , 2.37 (3H, s) , 6.88- 7.00(3H,m), 7.20-7.35 (4H,m) , 7.72-7.78 (IH, m)

(IV- 54) N- [l- (2-methylphenyl) -3-trimethylsilyl-2- propinylidene] -2-methylaniline

¹ H-NNR(CDCl ₃ ) δ(ppm) : 0.02 (9H, s) , 2.21 (3H, s) , 2.65 (3H, s) , 6.89- 6.93 (IH, m) , 7.00-7.06 (lH,m) , 7.13-7.35 (5H,m) _> 7.54-7.64 (lH,m) (IV-55) N- [l- (2 -fluorophenyl) -3-trimethylsilyl-2- propinylidene] -3-methylaniline

¹ H-NNR(CDCl ₃ ) δ (ppm) :0.10(9H,s) ,2.37 (3H,s) ,6.92-7.00 (2H,m) , 7.10-7.28 (4H,m) , 7.38-7.46 (IH, m) , 7.89-7.95 (IH, m) (IV-56) N- Cl- (2 -fluorophenyl) -3-trimethylsilyl-2 - propinylidene) -2-methylaniline

¹ H-NNR(CDCl ₃ ) δ (ppm) : 0.05 (9H ₇ s) , 2.21(3H ₇ S) ₇ 6.92- 6.97(lH,m), 7.02-7.26 (5H,m) , 7.39-7.47 (IH, m) , 7.94- 8.00 (lH,m)

(IV-57) N- Cl- (2 -fluorophenyl) -3-trimethylsilyl-2- propinylidene] -4-fluoroaniline

¹ H-NNR(CDCl ₃ ) δ (ppm) : 0.12(9H ₇ S) ₇ 7.02-7.25 (6H,m) , 7.39- 7.47(lH,m), 7.89-8.00 (IH, m)

(IV-58) N- Cl- (2 -fluorophenyl) -3-trimethylsilyl-2- propinylidene] -aniline

¹ H-NNR(CDCl ₃ ) δ(ppm) :0.09(9H,s) , 7.10-7.17 (5H,m) , 7.32- 7.47(2H,m) , 7.90-7.97 (IH, m)

(IV-59) N- Cl- (3 -fluorophenyl) -3-trimethylsilyl-2 - propinylidene) -4-methylaniline

¹ H-NNR(CDCl ₃ ) δ (ppm) : 0.18 (9H,s) , 7.10-7.21 (4H,m) , 7.24- 7.30(1H ₇ ItI) ₇ 7.38-7.46 (lH,m) , 7.86-7.98 (2H,m)

(IV-60) N- [l- (2,3-dimethylphenγl) -3-trimethylsilyl-2- propinylidene] -4-methylaniline

¹ H-NNR(CDCl ₃ ) δ(ppm) :0.10(9H,s) , 2.33(3H,s), 2.38(3H,s), 2.46(3H,s), 7.11-7.24 (6H,m) , 7.46-7.50 (IH, m) (IV-61) N- [l- (2-fluorophenyl) -3-trimethylsilyl-2- propinylidene] -3-chloroaniline

¹ H-NNR(CDCl ₃ ) δ(ppm) : 0.12 (9H,s) , 6.95-7.01 (IH,m) , 7.21- 7.33 (5H,m) , 7.41-7.49 (lH,m) , 7.90-7.97 (lH,m) (IV-62) N- [l- (2-fluorophenyl) -3-trimethylsilyl-2- propinylidenej -4-chloroaniline

¹ H-NNR(CDCl ₃ ) δ (ppm) : 0.12 (9H,s) , 7.04-7.27 (5H,m) , 7.30- 7.3β(lH,m), 7.40-7.47 (IH,m) , 7.89-7.96 (IH,m) (IV-63) N- Cl- (2 -fluorophenyl) -3-trimethylsilyl-2- propinylidene] -3-bromoaniline

¹ H-NNR(CDCl ₃ ) δ (ppm) : 0.12 (9H,s) , 7.10-7.31 (5H,m) , 7.40- 7.48(lH,m), 7.90-7.97 (IH, m)

(IV-64) N- Cl- (2 -fluorophenyl) -3-trimethylsilyl-2- propinylidene) -2-fluoroaniline

¹ H-NNR(CDCl ₃ ) δ(ppm) : 0.12 (9H,s) ,6.99-7.05 (2H,d _λ J=8.5Hz) ,7.10-7.35(2H,m),7.40-7.62(3H,m),7.90-7.96(lH,m)

(IV-65) N- Cl- (2 -fluorophenyl) -3-trimethylsilyl-2- propinylidene] -3 -fluoroaniline

¹ H-NNR(CDCl ₃ ) δ(ppm) :0.11(9H,s) , 6.84-6.90 (2H,m) , 7.11- 7.37(5H,m), 7.42-7.50 (IH, m) , 7.91-7.98 (IH, m) (IV-66) N- Cl- (2 -fluorophenyl) -3-trimethylsilyl-2-

propinylidene] -3 , 4-dimethylaniline

¹ H-NNR(CDCl ₃ ) δ(ppm) : 0.12 (9H,s) , 2.27(6H,s), 6.94- 7.23 (5H,m), 7.37-7.49 (IH, m) , 7.86-7.92 (IH, m) (IV- 67) N- [l- (4-methoxyphenyl) -3-trimethylsilyl-2- propinylidene] -4-methylaniline

¹ H-NNR(CDCl ₃ ) δ(ppm) : 0.14 (9H, s) , 2.35 (3H, s) , 3.86 (3H, s) , 6.95 (2H,d,J=8.7Hz) ,7.06 (2H, d, J=8. OHz) ,7.15 (2H, d, J=8.7Hz) ,8. 11 (2H,d, J=8.0Hz)

(IV-68) N- [l- (2,5-dichlorophenyl) -3-trimethylsilyl-2- propinylidene] -4-methylaniline

¹ H-NNR(CDCl ₃ ) δ (ppm) : 0.12(9H,s), 2.36 (3H, s) , 7.15- 7.20(4H,m), 7.28-7.38 (3H,m) , 7.65 (IH, d, J=2.6Hz) (IV-69) N- Cl- (2 -chloro- 6 -fluorophenyl) -3-trimethylsilyl-2- propinylidene] -4-methylaniline

¹ H-NNR(CDCl ₃ ) δ (ppm) :0.11(7H,s),0.23(2H,s),2.20(0.6H,s), 2.38 (2.4H,s) ,7.05-7.33 (7H,m)

(IV-70) N- Cl- (2, 6-dimethylphenyl) -3-trimethylsilyl-2- propinylidene] -4-methylaniline

¹ H-NNR(CDCl ₃ ) δ(ppm) :0.08 (6H,s) ,0.11(3H,s) , 2.18-2.41 (9H,m) , 6.88-7.15 (7H,m)

(IV-71) N- Cl- (2-fluoro-4-trifluoromethylphenyl) -3- trimethylsiIyI -2 -propinylidene] -4-methylaniline 1H-NNR(CDCl ₃ ) δ(ppm) : 0.14 (9H, s) , 2.37 (3H, s) , 7.14-7.22 (4H,m) , 7.36-7.51(2H,m) , 8.01-8.16 (IH, m) (IV-72) N- Cl- (1-naphthyl) -3-trimethylsilyl-2-

propinylidene] -4-methylaniline

¹ H-NNR(CDCl ₃ ) δ(ppm) : 0.12 (9H, s) , 2.40 (3H, s) , 7.17-7.24 (3H,m) , 7.45-7.59 (3H,m) , 7.84-7.96 (2H, m) , 8.07 (IH, d, J=7.4Hz) , 8.92 (IH, d, J=8.4Hz)

(IV-73) N- [l- (2-naphthyl) -3-trimethγlsilyl-2-propinylidene ] -4-methylaniline

¹ H-NNR(CDCl ₃ ) δ (ppm) :0.2 (9H,s) ,2.38 (3H,s) , 7.12-7.21 (4H, m) , 7.47-7.58(2H,m),7.83-7.99(3H,m),8.28(lH,s),8.16(lH,s) (IV-74) N- [l- (2, 5 -difluorophenyl) -3-trimethylsilyl-2- propinylidene) -4-methylaniline

¹ H-NNR(CDCl ₃ ) δ(ppm) : 0.12 (9H, s) , 2.35 (3H, s) , 7.04-7.20 (6H,m) , 7.59-7.66 (IH, m)

(IV-75) N- Cl- (4-chlorophenyl) -3-trimethylsilyl-2- propinylidene] -aniline

¹ H-NNR(CDCl ₃ ) δ (ppm) : 0.12 (9H,s) , 7.08-7.20 (2H,m) , 7.23- 7.46(2H,m), 8.08-8.14 (IH, m)

(IV-76) N- Cl- (4-chlorophenyl) -3-trimethylsilyl-2- propinylidene] -3-methylaniline

¹ H-NNR(CDCl ₃ ) δ (ppm) :0.14(9H,s),2.36(3H,s),6.89-7.00(3H,m), 7.21-7.27 (IH, m) , 7.42 (2H, d, J=8.3Hz) , 8.10 (2H, d, J=8.3Hz) (IV-77) N- Cl- (4-chlorophenyl) -3-trimethylsilyl-2- propinylidene) -2-chloroaniline

¹ H-NNR(CDCl ₃ ) δ (ppm) -.0.10 (9H,s) , 7.00-7.12 (2H,m) , 7.22- 7.48(3H,m), 8.15 (2H, d, J=8.4Hz) (IV-78) N- Cl- (4-chlorophenyl) -3-trimethylsilyl-2-

propinylidene] -3-chloroaniline

¹ H-NNR(CDCl ₃ ) δ (ppm) :0.16 (9H,s) ,6.98 (IH, d, J=7.7Hz) , 7.15(2H,s),7.22-7.32(2H,m),7.42 (2H, d, J=8.2Hz) , 8.10 (2H,d, J=8.2Hz)

(IV-79) N- [l- (4-chlorophenyl) -3-trimethylsilyl-2- propinylidene] -2-methylaniline

¹ H-NNR(CDCl ₃ ) δ(ppm) :0.10 (9H,s) ,6.95 (IH, d, J=7.5Hz) , 7.07 (IH, d, J=7.5Hz) , 7.13 -7.25 (2H,m) , 7.44 (2H, d, J=8.6Hz) , 8.13 (2H,d, J=8.6Hz)

(IV-80) N- Cl- (4-chlorophenyl) -3-trimethylsilyl-2- propinylidene] -4-fluoroaniline

¹ H-NNR(CDCl ₃ ) δ(ppm) : 0.17 (9H,s) ,7.02-7.17 (4H,m) , 7.43 (2H,d, J=8.2Hz) , 8.10 (2H, d, J=8.2Hz) (IV-81) N- Cl- (4-chlorophenyl) -3-trimethylsilyl-2- propinylidene) -3 -fluoroaniline

¹ H-NNR(CDCl ₃ ) δ (ppm) : 0.16 (9H,s) , 6.81-6.92 (3H,m) , 7.29- 7.38(lH,m), 7.44 (2H, d, J=8.4Hz) , 8.11 (2H, d, J=8.4Hz) (IV-82) N- Cl- (4-chlorophenyl) -3-trimethylsilyl-2- propinylidene] -2-fluoroaniline

¹ H-NNR(CDCl ₃ ) δ (ppm) : 0.12 (9H,s) , 7.05-7.19 (4H, m) , 7.44 (2H,d, J=8.2Hz) , 8.14 (2H, d, J=8.4Hz)

(IV-83) N- Cl- (2-chloro4-fluorophenyl) -3-trimethylsilyl-2- propinylidene] -4-methylaniline 1H-NNR(CDCl ₃ ) δ(ppm) : 0.12 (9H, s) , 7.38 (3H, s) , 7.03-7.10 (lH,m) ,

7.14-7.22 (5H,m) , 7.67-7.82 (IH, m)

(IV- 84) N- [l- (4-chlorophenyl) -3-trimethylsilyl-2- propinylidene) -4-chloroaniline

¹ H-NNR(CDCl ₃ ) δ(ppm) : 0.17 (9H,s) , 7.08 (2H, d, J=8.7Hz) , 7.34 (2H,d, J=8.7Hz) , 7.43 (2H, d, J=8.7Hz) ,8.10 (2H, d, J=8.7Hz) (IV-85) N- [l- (2 -fluoro-4-chlorophenyl) -3-trimethylsilyl-2- propinylidene] -4-methylaniline

¹ H-NNR(CDCl ₃ ) δ (ppm) :0.12(9H,s),2.36(3H,s),7.09-7.22(6H,m), 7.87 (IH, t, J=8.2Hz)

(IV-86) N- [l-cyclohexyl-3-trimethylsilyl-2-propinylidene ] -4-methylaniline

¹ H-NNR(CDCl ₃ ) δ(ppm) :0.08 (9H,s) , 1.20-2.03 (10H,m) ,2.40- 2.51(lH,m) , 6.90(2H,d, J=8.2Hz) , 7.10 (2H, d, J=8.2Hz) (IV-87) N- [l-t-buthyl 3-trimethylsilyl-2-propinylidene] - 4-methylaniline

¹ H-NNR(CDCl ₃ ) δ(ppm) : 0.06(9H,s) , 1.28 (9H, s) , 6.86(2H,d, J=8.0Hz) , 7.09 (2H,d,J=8. OHz)

(IV-88) N- [l- (2-furyl) -3-trimethylsilyl-2-propinylidene] - 4-methylaniline

¹ H-NNR(CDCl ₃ ) δ (ppm) : 0.18 (9H,s) , 2.36(3H,s), 6.52- 6.56(lH,m), 7.06 (IH, d, J=3.7Hz) , 7.13-7.21 (4H,m) , 7.58- 7.60 (IH, m)

(IV-89) N- Cl- (3-pyridyl) -3-trimethylsilyl-2-propinylidene ] -4-methylaniline

¹ H-NNR(CDCl ₃ ) δ(ppm) : 0.19 (9H, s) , 2.38 (3H, s) , 7.23-7.32 (4H,m) , 7.35-7.42 (IH, m) , 7.44 (IH, d, J=8. OHz) , 7.70 (IH, d, J=4.6Hz) ,

9 . 33 ( IH , s )

(IV- 90) N- [l- (2-thienyl) -3-trimethylsilyl-2-propinylidene ] -4-methylaniline

¹ H-NNR(CDCl ₃ ) δ(ppm) :0.18 (9H,s) ,2.34 (3H,s) ,7.06-7.16 (5H,m) , 7.40-7.46 (IH, m) , 7.66-7.71 (IH, m)

(IV-91) N- Cl- (2-chloro-3-pyridyl) -3-trimethylsilyl-2- propinylidene] -4-methylaniline

¹ H-NNR(CDCl ₃ ) δ (ppm) :0.15 (9H,s) ,2.39 (3H ₇ s) , 7.17-7.40 (5H ₇ m) , 8.00-8.05 (lH,m) , 8.45-8.50 (IH, m)

(IV-92) N- Cl- (5-chloro-2-thienyl) -3-trimethylsilyl-2- propinylidene] -4-methylaniline

¹ H-NNR(CDCl ₃ ) δ (ppm) : 0.19 (9H ₇ s) , 2.38(3H,s), 7.14- 7.21(4H,m), 7.31 (IH, d, J=8.2Hz) , 8.38-8.44 (lH,m)

Reference Production Example 93 (II-l) Production of N- (1-phenyl-2 -propinylidene) aniline

To a methanol solution (15 mL) of N- (l-phenyl-3- trimethylsiIyI-2-propinylidene) aniline (1.5 g) was added potassium carbonate (10 mg) at room temperature, and the mixture was stirred at the same temperature for 2 hours. The generated crystal was filtrated, and washed with cold methanol to obtain N- (l-phenyl-2-propinylidene) aniline (0.5 g) as a crystal.

¹ H-NMR (CDCl ₃ ) δ(ppm):3 .32 (IH ₇ s) , 7.07 to 7.68 (9H, m) , 8.26 (IH ₇ d)

Reference Production Examples 94 to 97

The following compounds were produced by the method according to reference Production Example 93.

(II-2) N- [l- (3-methoxyphenyl) -2-propinylidene) aniline ¹ H-NMR(CDCl ₃ ) δ (ppm) :3.30(lH,s) , 3.88 (3H,s) ,7.03~ 7.42 (7H,m) , 7.74~7.80 (2H,m)

(II-3) N- [l- (2 -chlorophenyl) -2-propinylidene] aniline 1H-NMR(CDCl ₃ )δ(ppm) : 3.33 (IH, s) , 7.05~7.73 (9H,m)

(II-4) N- [l- (2-nitrophenyl) -2-propinylidene) aniline 1H-NMR(CDCl ₃ ) δ (ppm) :3.45(lH,s),7.13~7.28(3H,m),7.37~ 7.47 (2H,m) , 7.28~8.40 (4H,m)

(II-5) N- [l- (4-phenylphenyl) -2-propinylidene) aniline 1H-NMR(CDCl ₃ ) δ (ppm) :3.34(lH,s),7.09~7.22(3H,m),7.35~ 7.51 (5H,m) ,7.61—7.73 (4H,m) ,8.23 —8.30 (2H,m)

Reference Production Example 98

Production of 1- (4-chlorophenyl) -2-methyl-2-propen-l-one To mixed liquid of 4-chloropropiophenone (20 g) and acetic anhydride (21.7 g) was added hexamethylenetetramine (23.6 g) and the mixture was stirred at room temperature for 30 minutes, then, stirred at 80°C for 3 hours. To the reaction mixture was added water (150 ml) , and pH was adjusted to 10 with 2N-sodium hydroxide, then, extracted with t-butyl methyl ether (three times) , washed with water,

dried, then, concentrated under reduced pressure and the resultant residue was subjected to silica gel column chromatography (hexane : ethyl acetate = 10:1) to obtain 1-

(4-chlorophenyl) -2-methyl-2-propen-l-one (10.6 g) .

¹ H-NNR (CDCl ₃ ) δ (ppm) : 2.07 (3H, s) , 5.60 (IH, s) , 5.92

(IH, s) , 7.42 (2H, d, J = 8.2 Hz), 7.69 (2H, d, J = 8.2 Hz)

Reference Production Examples 99 to 102

The following compounds were produced by the method according to reference Production Example 98.

1- (2 -fluorophenyl) -2-methyl-2-propene-l-on

¹ H-NNR(CDCl ₃ ) δ(ppm) :2.06(3H,s),5.68(lH,s),6.00(lH,s),7.07-

7.22 (2H,m) , 7.37-7.48 (2H,m)

1- (2-methylphenyl) -2-methyl-2-propene-l-on

¹ H-NNR(CDCl ₃ ) δ (ppm) : 2.04 (3H,s) , 2.44(3H,s), 5.85(lH,s),

5.95(lH,s), 7.02-7.65 (4H,m)

1- (2 , 5 -difluorophenyl) -2-methyl-2-propene-l-on

¹ H-NNR(CDCl ₃ ) δ(ppm) : 2.05 (3H, s) , 5.72 (IH, s) , 6.04 (IH, s) , 7.04-

7.17 (3H,m)

1- (2 , 4 -difluorophenyl) -2-methyl-2-propene-l-on

¹ H-NNR(CDCl ₃ ) δ(ppm) : 2.05 (3H, s) , 5.67 (IH, s) , 5.99 (IH, s) , 6.82-

6.97 (2H,m) ,7.41-7.48 (IH, m)

Next, formulation examples will be shown. Parts are by weight .

Formulation Example 1

Ten parts of any one of the present compounds 1 to 323 is dissolved in a mixture of 35 parts of xylene and 35 parts of N, N-dimethylformamide. Thereto 14 parts of polyoxyethylene styryl phenyl ether and 6 parts of calcium dodecylbenzenesulfonate are added, and mixed by stirring thoroughly to obtain a 10% emulsifiable concentrate.

Formulation Example 2

Twenty parts of any one of the present compounds 1 to 323 is added to a mixture of 4 parts of sodium lauryl sulfate, 2 parts of calcium lignin sulfonate, 20 parts of synthetic hydrous silicon oxide fine powder and 54 parts of diatomaceous earth, and mixed by stirring thoroughly to obtain a 20% wettable powder.

Formulation Example 3

One part of synthetic hydrous silicon oxide fine powder, 2 parts of calcium lignin sulfonate, 30 parts of bentonite and 65 parts of kaoline clay are added to 2 part of any one of the present compounds 1 to 323, and mixed by stirring thoroughly. To this mixture an appropriate amount of water is added. The mixture is further stirred, granulated with a granulator, and then air-dried to obtain

a 2% granule.

Formulation Example 4

One part of any one of the present compounds 1 to 323 is dissolved in an appropriate amount of acetone. Thereto 5 parts of synthetic hydrous silicon oxide fine powder, 0.3 part of PAP (isopropyl acid phosphate) and 93.7 parts of agalmatolite clay are added, and mixed by stirring thoroughly. The acetone is evaporated to obtain a 1% dust.

Formulation Example 5

Ten parts of any one of the present compounds 1 to 323, 30 parts of a mixture of cyclohexanone with dimethylsulfoxide (weight ratio 90/10) , 35 parts of a mixture of white carbon with polyoxyethylene alkylether sulfate ammonium salt (weight ratio 50/50) , and 25 parts of water are mixed and then finely-divided by a wet grinding method to obtain a 10% flowable formulation.

Formulation Example 6

Zero point one part of any one of the present compounds 1 to 323 is dissolved in a mixture of 5 parts of xylene and 5 parts of trichloroethane . This solution is mixed with 89.9 parts of deodorized kerosene to obtain a 0.1% oil solution.

Formulation Example 7

Ten milligrams of any one of the present compounds 1 to 323 is dissolved in 0.5 mL of acetone. This solution is mixed homogeneously with 5 g of a powdered solid animal feed (powdered solid feed for breeding, CE-2 manufactured by Clea Japan Inc . ) . The acetone was eveporated to obtain a poison bait.

Formulation Example 8

Ten parts of any one of the present compounds 1 to 323, 35 parts of a mixture of white carbon with polyoxyethylene alkylether sulfate ammonium salt (weight ratio 50/50) , and 55 parts of water are mixed and then finely-divided by a wet grinding method to obtain a 10% flowable formulation.

Formulation Example 9

Ten parts of the present compound 133 and 10 parts of any one of insecticides, acaricides, nematocides, fungicides, herbicides, phytohormone agents, plant growth regulators, synergists and crop injury-reducing agents listed in the group I described below are added into a mixture of 4 parts of sodium lauryl sulfate, 2 parts of calcium lignin sulfonate, 20 parts of synthetic hydrous

silicon oxide fine powder and 54 parts of diatomaceous earth, and mixed by stirring thoroughly to obtain a mixed wettable powder.

Formulation Example 10

Ten parts of the present compound 209 and 10 parts of any one of insecticides, acaricides, nematocides, fungicides, herbicides, phytohormone agents, plant growth regulators, synergists and crop injury-reducing agents listed in the group I described below are added into a mixture of 4 parts of sodium lauryl sulfate, 2 parts of calcium lignin sulfonate, 20 parts of synthetic hydrous silicon oxide fine powder and 54 parts of diatomaceous earth, and mixed by stirring thoroughly to obtain a mixed wettable powder.

Formulation Example 11

Ten parts of the present compound 233 and 10 parts of any one of insecticides, acaricides, nematocides, fungicides, herbicides, phytohormone agents, plant growth regulators, synergists and crop injury-reducing agents listed in the group I described below are added into a mixture of 4 parts of sodium lauryl sulfate, 2 parts of calcium lignin sulfonate, 20 parts of synthetic hydrous silicon oxide fine powder and 54 parts of diatomaceous

earth, and mixed by stirring thoroughly to obtain a mixed wettable powder.

Formulation Example 12

Ten parts of the present compound 243 and 10 parts of any one of insecticides, acaricides, nematocides, fungicides, herbicides, phytohormone agents, plant growth regulators, synergists and crop injury-reducing agents listed in the group I described below are added into a mixture of 4 parts of sodium lauryl sulfate, 2 parts of calcium lignin sulfonate, 20 parts of synthetic hydrous silicon oxide fine powder and 54 parts of diatomaceous earth, and mixed by stirring thoroughly to obtain a mixed wettable powder.

Formulation Example 13

Ten parts of the present compound 261 and 10 parts of any one of insecticides, acaricides, nematocides, fungicides, herbicides, phytohormone agents, plant growth regulators, synergists and crop injury-reducing agents listed in the group I described below are added into a mixture of 4 parts of sodium lauryl sulfate, 2 parts of calcium lignin sulfonate, 20 parts of synthetic hydrous silicon oxide fine powder and 54 parts of diatomaceous earth, and mixed by stirring thoroughly to obtain a mixed

wettable powder.

Formulation Example 14

Ten parts of the present compound 288 and 10 parts of any one of insecticides, acaricides, nematocides, fungicides, herbicides, phytohormone agents, plant growth regulators, synergists and crop injury-reducing agents listed in the group I described below are added into a mixture of 4 parts of sodium lauryl sulfate, 2 parts of calcium lignin sulfonate, 20 parts of synthetic hydrous silicon oxide fine powder and 54 parts of diatomaceous earth, and mixed by stirring thoroughly to obtain a mixed wettable powder.

Formulation Example 15

Ten parts of the present compound 293 and 10 parts of any one of insecticides, acaricides, nematocides, fungicides, herbicides, phytohormone agents, plant growth regulators, synergists and crop injury-reducing agents listed in the group I described below are added into a mixture of 4 parts of sodium lauryl sulfate, 2 parts of calcium lignin sulfonate, 20 parts of synthetic hydrous silicon oxide fine powder and 54 parts of diatomaceous earth, and mixed by stirring thoroughly to obtain a mixed wettable powder.

The group I consists of: any insecticides of :

(1) organic phosphorus compounds: acephate, aluminum phosphide, butathiofos, cadusafos, chlorethoxyfos, chlorfenvinphos, chlorpyrifos, σhlorpyrifos-methyl, cyanophos (CYAP) , diazinon, DCIP

(dichlorodiisopropyl ether) , dichlofenthion (ECP) , dichlorvos (DDVP) , dimethoate, dimethylvinphos , disulfoton, EPN, ethion, ethoprophos, etrimfos, fenthion (MPP), fenitrothion (MEP) , fosthiazate, formothion, hydrogen phosphide, isofenphos, isoxathion, malathion, mesulfenfos, methidathion (DMTP) , monocrotophos , naled (BRP) , oxydeprofos (ESP) , parathion, phosalone, phosmet (PMP) , pirimiphos-methyl, pyridafenthion, quinalphos, phenthoate

(PAP), profenofos, propaphos, prothiofos, pyraclorfos, salithion, sulprofos, tebupirimfos, temephos, tetrachlorvinphos, terbufos, thiometon, trichlorphon (DEP) , vamidothion, phorate and cadusafos;

(2) carbamate compounds: alanycarb, bendiocarb, benfuracarb, BPMC, carbaryl, carbofuran, carbosulfan, cloethocarb, ethiofencarb, fenobucarb, fenothiocarb, fenoxycarb, furathiocarb, isoprocarb (MIPC) , metolcarb, methomyl, methiocarb, NAC, oxamyl, pirimicarb, propoxur (PHC) , XMC, thiodicarb, xylylcarb and aldicarb;

(3) synthetic pyrethroid compounds: acrinathrin, allethrin, benfluthrin, beta-cyfluthrin, bifenthrin, cycloprothrin, cyfluthrin, cyhalothrin, cypermethrin, empenthrin, deltamethrin, esfenvalerate, ethofenprox, fenpropathrin, fenvalerate, flucythrinate, flufenoprox, flumethrin, fluvalinate, halfenprox, imiprothrin, permethrin, prallethrin, pyrethrins, resmethrin, sigma-cypermethrin, silafluofen, tefluthrin, tralomethrin, transfluthrin, tetramethrin, phenothrin, cyphenothrin, alpha-cypermethrin, zeta-cypermethrin, lambda-cyhalothrin, gamma-cyhalothrin, furamethrin, tau- fluvalinate, metofluthrin, 2 , 3 , 5 , 6-tetrafluoro-4- methylbenzyl 2 , 2-dimethyl-3- (1- propenyl) cyclopropanecarboxylate, 2,3,5, 6-tetrafluoro-4-

(methoxymethyl) benzyl 2 , 2-dimethyl-3- (2-methyl-1- propenyl) cyclopropanecarboxylate, 2,3,5, 6-tetrafluoro-4-

(methoxymethyl) benzyl 2 , 2-dimethyl-3- (2-cyano-l- propenyl) cyclopropanecarboxylate, and 2 , 3 , 5, 6-tetrafluoro- 4- (methoxymethyl) benzyl 2,2,3,3- tetramethylcyclopropanecarboxylate;

(4) nereistoxin compounds: cartap, bensultap, thiocyclam, monosultap and bisultap;

(5) neonicotinoid compounds: imidacloprid, nitenpyram, acetamiprid, thiamethoxam,

thiacloprid and clothianidin;

(6) benzoylurea compounds: chlorfluazuron, bistrifluron, diafenthiuron, diflubenzuron, fluazuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron, triflumuron and triazuron;

(7) phenylpyrazole compounds: acetoprole, ethiprole, fipronil, vaniliprole, pyriprole and pyrafluprole;

(8) Bt toxin insecticides: live spores derived from and crystal toxins produced from Bacillus thuringiesis and a mixture thereof;

(9) hydrazine compounds: chromafenozide, halofenozide, methoxyfenozide and tebufenozide ;

(10) organic chlorine compounds: aldrin, dieldrin, dienochlor, endosulfan and methoxychlor;

(11) natural insecticides: machine oil and nicotine sulfate;

(12) other insecticides: avermectin-B, bromopropylate, buprofezin, chlorphenapyr, cyromazine, D-D (1, 3-dichloropropene) , emamectin-benzoate, fenazaquin, flupyrazofos, hydroprene, methoprene, indoxacarb, metoxadiazone, milbemycin-A,

pymetrozine, pyridalyl, pyriproxyfen, spinosad, sulfluramid, tolfenpyrad, triazamate, flubendiamide, lepimectin, arsenic acid, benclothiaz, calcium cyanamide, calcium polysulfide, chlordane, DDT, DSP, flufenerim, flonicamid, flurimfen, formetanate, metarn-ammonium, metam- sodium, methyl bromide, potassium oleate, protrifenbute, spiromesifen, sulfur, metaflumizone, spirotetramat, pyrifluquinazone, spinetoram, chlorantraniliprole, tralopyril, a compound represented by the following formula (A) :

wherein X ^al represents a methyl group, a chlorine atom, a bromine atom or a fluorine atom, X ^a2 represents a fluorine atom, a chlorine atom, a bromine atom, a C1-C4 haloalkyl grop or a C1-C4 haloalkoxy group, X ^a3 represents a fluorine atom, a chlorine atom or a bromine atom, X ^a4 represents an optionally substituted C1-C4 alkyl group, an optionally substituted C3-C4 alkenyl group, an optionally substituted C3-C4 alkynyl group, an optionally substituted C3-C5 cycloalkylalkyl group or a hydrogen atom, X ^a5 represents a hydrogen atom or a methyl group, X ^a6 represents a hydrogen

atom, a fluorine atom or a chlorine atom, and X ^a7 represents a hydrogen atom, a fluorine atom or a chlorine atom; a compound represented by the following formula (B) :

wherein X ^bl represents a X ^b2 -NH-C (=0) group, a X ^b2 -C (=0) -NH- CH ₂ group, a X ^b3 -S (0) group, an optionally substituted pyrrol-1-yl group, an optionally substituted imidazol-1-yl group, an optionally substituted pyrazol-1-yl group, or an optionally substituted 1, 2 , 4-triazol-l-yl group, X ^b2 represents an optionally substituted C1-C4 haloalkyl group, such as a 2 , 2 , 2-trifluoroethyl group, or an optionally substituted C3-C6 cycloalkyl group, such as a cyclopropyl group, X ^b3 represents an optionally substituted C1-C4 alkyl group, such as a methyl group, and X ^b4 represents a hydrogen atom, a cyano group or a methyl group,- a compound represented by the following formula (C) :

wherein X represents an optionally substituted C1-C4

alkyl group, such as a 3 , 3 , 3-trifluoropropyl group, an optionally substituted C1-C4 alkoxy group, such as a 2,2,2- trichloroethoxy group, an optionally substituted phenyl group, such as a 4 -cyanophenyl group, or an optionally substituted pyridyl group, such as a 2-chloro-3-pyridyl group, X ^c2 represents a methyl group or a trifluoromethylthio group, and X ^c3 represents a methyl group and a halogen atom; any acaricides of acequinocyl, amitraz, benzoximate, bifenazate, bromopropylate, chinomethionate, chlorobenzilate, CPCBS (chlorfenson) , clofentezine, cyflumetofen, kelthane (dicofol) , etoxazole, fenbutatin oxide, fenothiocarb, fenpyroximate, fluacrypyrim, fluproxyfen, hexythiazox, propargite (BPPS) , polynactins, pyridaben, pyrimidifen, tebufenpyrad, tetradifon, spirodiclofen, spiromesifen, spirotetramat , amidoflumet and cyenopyrafen; any nematicides of DCIP, fosthiazate, levamisol hydrochloride, methylisothiocyanate, morantel tartarate and imicyafos; any fungicides of azole fungicidal compounds such as propiconazole, prothioconazole, triadimenol, prochloraz, penconazole, tebuconazole, flusilazole, diniconazole, bromuconazole, epoxiconazole, difenoconazole, cyproconazole, metconazole, triflumizole, tetraconazole,

myclobutanil, fenbuconazole, hexaconazole, fluquinconazole, triticonazole, bitertanol, imazalil, and flutriafol; cyclic amine fungicidal compouds such as fenpropimorph, tridemorph, and fenpropidin; benzimidazole fungicidal compounds such as carbendezim, benomyl , thiabendazole, and thiophanate-methyl ; procymidone, cyprodinil, pyrimethanil , diethofencarb, thiuram, fluazinam, mancozeb, iprodione, vinclozolin, chlorothalonil, captan, mepanipyrim, fenpiclonil, fludioxonil, dichlofluanid, folpet, kresoxim-methyl, azoxystrobin, trifloxystrobin, fluoxastrobin, picoxystrobin, pyraclostrobin, dimoxystrobin, spiroxamine, quinoxyfen, fenhexamid, famoxadone, fenamidone, zoxamide, ethaboxam, amisulbrom, iprovalicarb, benthiavalicarb, cyazofamid, mandipropamid, boscalid, metrafenone, fluopiran, bixafen, cyflufenamid, and proquinazid; any herbicides and any phytohormone agents of:

(1) phenoxyfatty acid herbicidal compounds such as 2,4-PA, MCP, MCPB, phenothiol, mecoprop, fluroxypyr, triclopyr, clomeprop, and naproanilide;

(2) benzoic acid herbicidal compounds such as 2,3,6- TBA, dicamba, clopyralid, picloram, aminopyralid, quinclorac, and quinmerac;

(3) urea herbicidal compounds such as diuron, linuron, chlortoluron, isoproturon, fluometuron, isouron,

tebuthiuron, methabenzthiazuron, cumyluron, daimuron, and methyl-daimuron;

(4) triazine herbicidal compounds such as atrazine, ametoryn, cyanazine, simazine, propazine, simetryn, dimethametryn, prometryn, metribuzin, and triaziflam;

(5) bipyridinium herbicidal compounds such as paraquat, and diquat;

(6) hydroxybenzonitrile herbicidal compounds such as bromoxyni1 and ioxyni1 ;

(7) dinitroaniline herbicidal compounds such as pendimethalin, prodiamine, and trifluralin;

(8) organic phosphorus herbicidal compounds such as amiprofos-methyl, butamifos, bensulide, piperophos, anilofos, glyphosate, glufosinate, and bialaphos;

(9) carbamate herbicidal compounds such as di-allate, tri-allate, EPTC, butylate, benthiocarb, esprocarb, molinate, dimepiperate, swep, chlorpropham, phenmedipham, phenisopham, pyributicarb, and asulam;

(10) acid amide herbicidal compounds such as propanil, propyzamide, bromobutide, and etobenzanid;

(11) chloroacetanilide herbicidal compounds such as acetochlor, alachlor, butachlor, dimethenamid, propachlor, metazachlor, metolachlor, pretilachlor, thenylchlor, and pethoxamid;

(12) diphenylether herbicidal compounds such as

acifluorfen-sodium, bifenox, oxyfluorfen, lactofen, fomesafen, chlomethoxyn.il, and aclonifen;

(13) cyclic imide herbicidal compounds such as oxadiazon, cinidon-ethyl, carfentrazone-ethyl, surfentrazone, flumiclorac-pentyl, flumioxazin, pyraflufen- ethyl, oxadiargyl, pentoxazone, fluthiacet-methyl, butafenacil, and benzfendizone;

(14) pyrazole herbicidal compounds such as benzofenap, pyrazolate, pyrazoxyfen, topramezone, and pyrasulfotole;

(15) triketone herbicidal compounds such as isoxaflutole, benzobicyclon, sulcotrione, mesotrione, tembotrione, and tefuryltrione;

(16) aryloxyphenoxypropionic acid herbicidal compounds such as clodinafop-propargyl, cyhalofop-butyl , diclofop- methyl, fenoxaprop-ethyl, fluazifop-butyl, haloxyfop- methyl, and quizalofop-ethyl ;

(17) trioneoxime herbicidal compounds such as alloxydim-sodium, sethoxydim, butroxydim, clethodim, cloproxydim, cycloxydim, tepraloxydim, tralkoxydim, and profoxydim;

(18) sulfonylurea herbicidal compounds such as chlorsulfuron, sulfometuron-methyl, metsulfuron-methyl, chlorimuron-ethyl, tribenuron-methyl, triasulfuron, bensulfuron-methyl, thifensulfuron-methyl, pyrazosulfuron- ethyl, primisulfuron-methyl, nicosulfuron, amidosulfuron,

cinosulfuron, imazosulfuron, rimsulfuron, halosulfuron- methyl, prosulfuron, ethametsulfuron-methyl, triflusulfuron-methyl, flazasulfuron, cyclosulfamuron, flupyrsulfuron, sulfosulfuron, azimsulfuron, ethoxysulfuron, oxasulfuron, iodosulfuron-methyl-sodium, foramsulfuron, mesosulfuron-methyl, trifloxysulfuron, tritosulfuron, orthosulfamuron, flucetosulfuron, and 1- (2- chloro-6 -propylimidazo [1, 2-a] pyridazin-3-ylsulfonyl) -3- (4 , 6-dimethoxypyrimidin-2-yl) urea;

(19) imidazolinone herbicidal compounds such as imazamethabenz-methyl, imazamethapyr, imazamox, imazapyr, imazaquin, and imazethapyr;

(20) sulfonamide herbicidal compounds such as flumetsulam, metosulam, diclosulam, florasulam, cloransulam-methyl , penoxsulam, and pyroxsulam;

(21) pyrimidinyloxybenzoic acid herbicidal compounds such as pyrithiobac-sodium, bispyribac-sodium, pyriminobac- methyl, pyribenzoxim, and pyriftalid; and

(22) other herbicidal compounds such as bentazon, bromacil, terbacil, chlorthiamid, isoxaben, dinoseb, amitrole, cinmethylin, tridiphane, dalapon, diflufenzopyr- sodium, dithiopyr, thiazopyr, flucarbazone-sodium, propoxycarbazone-sodium, mefenacet, flufenacet, fentrazamide, cafenstrole, indanofan, oxaziclomefone, benfuresate, ACN, pyridate, chloridazon, norflurazon,

flurtamone, diflufenican, picolinafen, beflubutamid, clomazone, amicarbazone, pinoxaden, and thiencarbazone- methyl ; any plant growth regulators of hymexazol, paclobutrazol, uniconazole-P, inabenfide, prohexadione- calcium, aviglycine, 1-naphthylacetamide, abscisic acid, indolebutyric acid, ethychlozate ethyl, ethephon, cloxyfonac, chlormequat, dichlorprop, gibberellin, prohydrojasmon, benzylaminopurine, forchlorfenuron, maleic hydrazide, calcium peroxide, mepiquat-chloride) and 4 -CPA (4-chlorophenoxyacetic acid) ; any synergists of piperonyl butoxide, sesamex, sulfoxide, N- (2-ethylhexyl) -8,9, 10-trinorborn-5-ene-2 , 3- dicarboximide (MGK 264) , N-declyimidazole, WARF- antiresistant, TBPT, TPP, IBP, PSCP, methyl iodide (CH3I) , t-phenylbutenone, diethylmaleate, DMC, FDMC, ETP, and ETN; and any crop injury-reducing agents of benoxacor, cloquintocet-mexyl , cyometrinil, daimuron, dichlormid, fenchlorazole-ethyl, fenclorim, flurazole, fluxofenim, furilazole, mefenpyr-diethyl , MG191, oxabetrinil, allidochlor, isoxadifen-ethyl, cyprosulfamide, fluxofenim, and 1, 8-naphthalic anhydride.

Next, test examples will show that the compound of the

present invention is useful for controlling pests.

Dilution A for test in Test Examples 1 to 8 was prepared by mixing the following components, then, finely grinding the mixture by a wet grinding method to obtain a 10% formulation for test, further, diluting the formulation for test with ion exchange water to give the dilution at the concentration of 500 ppm.

Composition of dilution A for test

Any one of the present compounds 1 to 323

10 parts

Mixture of dimethyl sulfoxide and cyclohexanone (dimethyl sulfoxide content: 10 wt%)

30 parts

Mixture of polyoxyethylenealkylether sulfate ammonium salt and white carbon (mixing weight ratio 1:1)

35 parts Water 25 parts

Dilution B (500 ppm) for test in Test Examples 9 to 10 was prepared by dissolving 30 mg of any one of the present compounds 1 to 323 in 0.075 mL of a mixture of xylene and N, N-dimethylformamide (mixing volume ratio; xylene :N, N- dimethylformamide = 1:1), further, adding 0.04 mL of a mixture of xylene and Solpole 3005 X (registered trade

mark: manufactured by TOHO Chemical Industry Co., Ltd.) (mixing volume ratio; xylene : Solpole 3005X = 1:9), and diluting the mixture with ion exchange water to give the dilution at the concentration of 500 ppm.

Test Example 1 (Spodoptera litura)

On the bottom of a polyethylene cup having a diameter of 5.5 cm, filter paper of the same size as the bottom was laid. An artificial feed (Insecta LF, NOSAN Corporation) sliced to a thickness of 6 mm and further cut into the half was placed on the filter paper. Then 2 mL of the dilution A was poured into the polyethylene cup. The dilution in the cup was dried under air, and then 5 fourth-instar larvae of Spodoptera litura were released into the cup, and the cup was capped. Six (6) days after, the number of dead insects was counted.

Mortality was calculated by the following formula, and evaluated by indices of 4: mortality 100%, 3: mortality 80 to 99%, 2: mortality 60-79%, 1: mortality 30 to 59%, or 0: mortality 0 to 29%.

Mortality (%) = (the number of dead insects/the number of tested insects) XlOO

The index was 3 or more in each dilution obtained from the present compound 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 20, 22, 23, 25, 27, 31, 34, 35, 37, 38,

40, 41, 42, 44, 46, 53, 54, 56, 57, 58, 59, 60, 61, 62, 63,

64, 65, 66, 67, 68, 69, 70, 72, 73, 75, 76, 77, 78, 79, 80,

81, 82, 83, 84, 85, 86, 87, 88, 89, 90, 91, 92, 93, 94, 95, 96, 97, 98, 100, 102, 103, 104, 105, 106, 107, 108, 109,

110, 111, 112, 117, 122, 132, 133, 134, 135, 136, 137, 138,

139, 140, 142, 143, 144, 145, 146, 150, 151, 152, 153, 157,

161, 162, 163, 164, 165, 166, 167, 168, 169, 170, 171, 172,

173, 174, 175, 176, 192, 193, 194, 196, 200, 201, 205, 207,

208, 209, 210, 211, 212, 213, 214, 215, 216, 221, 223, 224,

225, 226, 227, 228, 229, 230, 231, 233, 234, 235, 236, 237,

238, 239, 240, 241, 242, 243, 244, 245, 246, 247, 248, 249,

250, 251, 252, 253, 254, 255, 256, 257, 262, 263, 264, 265,

267, 269, 270, 272, 274, 275, 276, 278, 279, 280, 281, 283,

284, 285, 286, 287, 288, 289, 290, 291, 292, 293, 294, 295,

296, 300, 301, 302, 303, 304, 305, 306, 307, 310, 311,

312, 313, 314, 315, 320, 322 or 323.

Test Example 2 (Adoxophyes orana)

On the bottom of a polyethylene cup having a diameter of 5.5 cm, filter paper of the same size as the bottom was laid. An artificial feed (Silkmate 2S, NOSAN Corporation) sliced to a thickness of 2 mm was placed on the filter paper. Then 1 mL of the dilution A was poured into the polyethylene cup. The dilution in the cup was dried under air. Then the filter paper having a diameter of 5.5 cm was

placed on the artificial feed, and 30 first-instar larvae of Adoxophyes orana were released into the cup, and the cup was capped. Seven (7) days after, the number of dead insects was counted.

Mortality was calculated by the following formula, and evaluated by indices of 4: mortality 100%, 3: mortality 80 to 99%, 2: mortality 60-79%, 1: mortality 30 to 59%, or 0: mortality 0 to 29%.

Mortality (%) = (the number of dead insects/the number of tested insects) XlOO

The index was 3 or more in each dilution obtained from the present compound 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 19, 20, 21, 22, 23, 24, 25, 27, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 53, 54, 56, 57, 58, 59, 60, 61, 62, 63, 64, 65, 66, 67, 68, 69, 71, 72, 73, 74, 75, 76, 77, 78, 79, 80, 81, 82, 83, 84, 85, 86, 87, 88, 89, 90, 91, 92, 93, 94, 95, 96, 97, 98, 99, 100, 101, 102, 103, 104, 105, 106, 107, 108, 109, 110, 111, 112, 113, 117, 118, 119, 120, 121, 122, 123, 129, 130, 131, 132, 133, 134, 135, 136, 137, 138, 139, 140, 142, 143, 144, 145, 146, 149, 150, 151, 154, 155, 157, 158, 161, 162, 163, 164, 165, 166, 167, 168, 169, 170, 171, 172, 173, 174, 175, 176, 177, 180, 181, 182, 184, 186, 187, 192, 193, 194, 195, 196, 197, 198, 200, 201, 202, 203, 204, 205, 206, 207, 208, 209, 210, 211, 212, 213, 214, 215, 216, 219, 220, 221,

222, 223, 224, 225, 226, 227, 228, 229, 230, 231, 233, 234,

235, 236, 237, 238, 239, 240, 241, 242, 243, 244, 245, 246,

247, 248, 249, 250, 251, 252, 253, 254, 255, 256, 257, 262,

263, 264, 265, 267, 269, 270, 271, 272, 274, 275, 276, 277,

278, 279, 280, 281, 283, 284, 285, 287, 288, 289, 290, 291,

292, 293, 294, 295, 296, 297, 298, 299, 300, 301, 302, 303,

304, 305, 306, 307, 310, 311, 312, 313, 314, 315, 317, 322 or 323.

Test Example 3 (Aphis gossypii)

On cucumber leaves in the single-leaf period cultivated in a 1-ounce cup, 30 first-instar larvae of Aphis gossypii were released. Next day, 20 mL of the dilution A was sprayed into the leaves. Six (6) days after, the number of survived insects was counted.

Survival rate against non-treated leaves was calculated by the following formula and evaluated by indices of 4: survival rate 0%, 3: survival rate 1 to 10%, 2: survival rate 11 to 40%, 1: survival rate 41 to 70%, or 0: survival rate >70%.

Survival rate against non-treated leaves (%) = (the number of survived insects in the tested leaves /the number of survived insects in non-treated leaves) XlOO

The index was 3 or more in each dilution obtained from the present compound 10, 11, 12, 13, 15, 28, 31, 66, 67,

68, 69, 84, 124, 126, 127, 128, 129, 131, 132, 171, 213, 214, 215, 216, 227, 228, 229, 233, 234, 235, 236, 237, 238, 239, 241, 242, 243, 244, 245, 246, 247, 248, 250, 252, 255, 256, 257, 265, 268, 270, 272, 274, 276, 278, 279, 285, 288, 290, 293, 294, 296, 297, 300, 301, 302, 307, 311 or 322.

Test Example 4 (Nilaparvata lugens)

Paddies of 2 to 3-leaves period calculated in a 90 mL plastic cup was cut at the part distant from ground boundary by 5 cm or more. The dilution A was sprayed into the cut paddies in an amount of 20 mL per pot. The sprayed dilution was dried under air. Then 30 first to second- instar larvae of Nilaparvata lugens were released into the cup, and the cup was capped. Six (6) days after the treatment, the number of survived insects was counted.

Survival rate against non-treated leaves was calculated by the following formula and evaluated by indices of 4: survival rate 0%, 3: survival rate 1 to 10%, 2: survival rate 11 to 40%, 1: survival rate 41 to 70%, or 0: survival rate >70%.

Survival rate against non-treated leaves (%) = (the number of survived insects in test district/the number of survived insects in non-treated leaves) XlOO

The index was 3 or more in each dilution obtained from the present compound 1, 21, 58, 76, 77, 79, 86, 108, 132,

133, 134, 135, 136, 137, 139, 140, 142, 143, 148, 153, 162,

163, 172, 176, 229, 235, 236, 237, 242, 243, 244, 245, 246,

247, 252, 265, 269, 270, 272, 274, 275, 276, 278, 280, 283,

284, 285, 290, 293, 294, 307, 311, or 322.

Test Example 5 (Musca domestica)

On the bottom of a polyethylene cup having a diameter of 5.5 cm, filter paper of the same size as the bottom was laid. The dilution A (0.7 mL) was dropped on the filter paper, and further, 30 mg of sucrose was placed thereon as a feed. Into the polyethylene cup, ten female adult insects of Musca domestica were released, and the cup was capped. Twenty-four (24) hours after, the number of dead insects was counted.

Mortality was calculated by the following formula, and evaluated by indices of 4: mortality 100%, 3: mortality 70 to 99%, 2: mortality 40-69%, 1: mortality 10 to 39%, or 0: mortality 0 to 9%.

Mortality (%) = (the number of dead insects/the number of tested insects) XlOO

The index was 3 or more in each dilution obtained from the present compound 1, 2, 3, 4, 5, 6, 7, 8, 10, 11, 12, 13, 15, 17, 19, 20, 22, 23, 25, 26, 27, 28, 29, 30, 31, 57, 58, 60, 61, 63, 64, 65, 66, 67, 69, 71, 72, 75, 76, 77, 79, 80, 81, 83, 85, 86, 89, 90, 127, 128, 132, 133, 134, 135,

136, 137, 138, 139, 140, 142, 143, 144, 145, 146, 148, 150,

151, 157, 162, 163, 165, 166, 167, 168, 170, 171, 172, 173,

175, 176, 207, 208, 209, 211, 213, 214, 215, 216, 223, 224,

225, 226, 227, 228, 229, 230, 234, 235, 236, 237, 238, 243,

244, 245, 247, 248, 249, 250, 251, 253, 254, 255, 256, 257,

265, 266, 267, 268, 269, 270, 272, 273, 274, 275, 276, 277,

278, 279, 280, 281, 284, 285, 286, 287, 288, 289, 290, 291,

292, 293, 294, 295, 296, 297, 298, 299, 300, 301, 302, 303,

304, 305, 306, 307, 313 or 315.

Test Example 6 (Blattalla germanica)

On the bottom of a polyethylene cup having a diameter of 5.5 cm, filter paper of the same size as the bottom was laid, and 0.7 mL of the dilution A was dropped on the filter paper, and 30 mg of sucrose was placed thereon as a feed. In the polyethylene cup, two male adult insects of Blattalla germanica were released, and the cup was capped. Six (6) days after, the number of dead insects was counted.

Evaluation was performed by indices of 4 : all death, 2: half death, or 0: all survived

The index was 4 in each dilution obtained from the present compound 132, 133, 134, 135, 136, 137, 139, 140, 141, 142, 143, 144, 148, 154, 155, 158, 162, 163, 165, 166, 167, 170, 171, 172, 173, 174, 175, 176, 205, 207, 208, 233, 234, 235, 236, 237, 238, 241, 243, 244, 247, 253, 255, 269,

270 , 272 , 273 , 274 , 278 , 279 , 280 , 281 , 285 , 287 , 288 , 289 , 290 , 293 , 300 , 3 01 , 302 , 306 , 3 07 , 313 or 315 .

Test Example 7 (Culex pipiens pallens)

The dilution A (0.7 mL) was added to 100 mL of ion exchange water (effective component concentration: 3.5 ppm) . In the dilution as obtained, 20 last-instar larvae of Culex pipiens pallens were released, and one day after, the number of dead insects was counted.

Mortality was calculated by the following formula, and evaluated by indices of 4: mortality 91 to 100%, 2: mortality 11 to 90%, or 0: mortality 0 to 10%.

Mortality (%) = (the number of dead insects/the number of tested insects) XlOO

The index was 4 in each dilution obtained from the present compound I ₇ 2, 3, 4, 5, 6, 7, 8, 10, 11, 12, 13, 14, 15, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 37, 38, 39, 40, 41, 42, 44, 46, 47, 48, 49, 51, 53, 55, 56, 57, 58, 59, 60, 61, 62, 63, 64, 65, 66, 67, 68, 69, 71, 72, 75, 76, 77, 79, 80, 83, 85, 86, 88, 89, 90, 95, 96, 98, 114, 115, 117, 118, 120, 122, 123, 124, 125, 131, 132, 133, 134, 135, 136, 137, 138, 139, 140, 142, 143, 144, 145, 146, 147, 148, 149, 150, 151, 152, 153, 154, 155, 156, 157, 158, 207, 213, 215, 223, 227, 233, 234, 235, 236, 237, 238, 239, 240, 241, 242, 243, 244, 245, 246, 247,

248, 251, 252, 253, 254, 255, 256, 257, 262, 264, 265, 266,

267, 269, 270, 271, 272, 273, 274, 275, 276, 278, 279, 280,

281, 282, 283, 284, 285, 286, 287, 288, 289, 291, 292, 293,

294, 295, 296, 297, 298, 299, 300, 301, 302, 303, 304, 305,

306, 307, 312, 313 or 314.

Test Example 8 (Tetranychus urticae)

Kidney bean leaf (I) parasitized with a large number of Tetranychus urticae were cut and placed on kidney bean leaf (II) cultivated in 3-ounce cup after one week from sowing, and left for one day to allow Tetranychus urticae to parasitize the leaf (II) . Next day, the leaf (I) was removed from the leaf (II) with a pincette, then, 20 mL of the dilution A was sprayed into the leaf (II) . Eight (8) days after, the number of female adult insects of Tetranychus urticae survived on the leaf (II) in each cup was counted.

Evaluation was performed by indices of 4 : survived number 0 to 3 , 3: survived number 4 to 10, 2: survived number 11 to 20, 1: survived number 21 to 30, or index 0: survived number 31 or more

The index was 3 or more in each dilution obtained from the present compound 4, 8, 11, 13, 15, 76, 77, 79, 81, 63, 84, 85, 86, 87, 88, 89, 90, 221, 223, 224, 239, 241, 243, 244, 247, 255, 256, 270, 276, 278, 279, 280, 285, 288, 290

or 293 .

Test Example 9 (Plutella xylostella)

Into Brassicae oleracea in 4-leaves period, 20 mL of the dilution B was sprayed and dried. Then, parts above ground of Brassicae oleracea were cut and placed in a polyethylene cup (content volume: 100 mL) together with 5 second-instar larvae, and stored at 25°C. Five (5) days after, the number of dead insects was counted.

Mortality was calculated by the following formula, and evaluated by indices of 4: mortality 100%, 3: mortality 80 to 99%, 2: mortality 60-79%, 1: mortality 30 to 59%, or 0: mortality 0 to 29%.

Mortality (%) = (the number of dead insects/the number of tested insects) XlOO

The index was 3 or more in each dilution obtained from the present compound 2, 3, 4, 6, 8, 10, 11, 12, 13, 14, 15, 17, 38, 39, 40, 41, 42, 44, 45, 46, 47, 48, 51, 53, 54, 58, 59, 60, 61, 62, 63, 65, 66, 67, 70, 71, 72, 73, 75, 76, 77, 78, 79, 80, 81, 82, 83, 84, 85, 86, 87, 88, 89, 90, 91, 92, 93, 94, 95, 96, 97, 98, 99, 101, 103, 104, 105, 106, 107, 108, 109, 110, 111, 132, 133, 134, 135, 136, 137, 138, 139, 140, 142, 143, 144, 145, 146, 148, 154, 156, 157, 158, 159, 161, 163, 165, 166, 170, 177, 181, 183, 184, 186, 192, 193, 194, 195, 196, 197, 199, 200, 201, 202, 205, 206, 207, 208,

209, 210, 211, 212, 213, 214, 215, 216, 221, 223, 224, 225,

226, 227, 228, 229, 230, 231, 233, 234, 235, 236, 237, 238,

239, 240, 241, 242, 243, 244, 245, 246, 247, 248, 249, 250,

251, 252, 253, 254, 255, 256, 257, 262, 263, 264, 265, 266,

267, 268, 269, 270, 271, 272, 274, 275, 276, 277, 278, 279,

281, 283, 284, 285, 287, 288, 289, 290, 291, 292, 293,

294, 295, 296, 297, 298, 300, 301, 302, 303, 304, 305, 306,

307, 311, 312, 313, 316 or 322.

Test Example 10 (Bemisia tabaci)

From burseraceous cultivated for about 3 weeks in a 3- ounce cup, all leaves were removed excepting second true leaves. On this burseraceous, adult insects of Bemisia tabaci were released and left for 3 days to be allowed to lay eggs. Then the adult insects were removed from the burseraceous, and the eggs were stored in a greenhouse for 8 days to cause hatch. The mixture of the dilution B (20 mL) with 3000-fold-diluted Dyne (Dyne, registered trade mark, manufactured by Takeda Pharmaceutical Company limited) was sprayed into the burseraceous. Seven (7) days after, mortality was checked.

Evaluation was performed by indices of 4 : mortality 100%, 3: mortality 90 to 99% (larva adhesion area is 1 to 10% of non-treated area), 2: mortality 60 to 89% (larva adhesion area is 11 to 40% of non-treated area), 1:

mortality 30 to 59% (larva adhesion area is 41 to 70% of non-treated area), or 0: mortality 0 to 29% (larva adhesion area is 71% or more of non-treated area) .

The index was 3 or more in dilution liquids obtained from the present compound 11, 132, 171, 209, 210, 211, 212, 213, 214, 215, 216, 227, 228, 229, 231, 233, 234, 236, 237, 238, 239, 241, 243, 244, 245, 246, 247, 248, 250, 252, 253, 256, 257, 265, 272, 274, 276, 277, 279, 288, 290, 293, 296, 297, 311 or 322.

Industrial Applicability

The compound of the present invention shows an excellent controlling effect on pests, thus, is useful as an active ingredient of a pesticidal composition.