DESCRIPTION

AMIDE COMPOUND AND USE THEREOF FOR CONTROLLING HARMFUL ARTHROPODS

TECHNICAL FIELD

[ 0001]

The present invention relates to amide compounds and use thereof for controlling . harmful arthropods.

BACKGROUND ART

[ 0002]

Hitherto, many agents for controlling harmful arthropods have been developed for controlling harmful arthropods and have been in practical use. Certain amide compounds are described in "JP-57-75961-A" and "Pesticide Science, 1987, 18, pp.211-221". [ 0003]

DISCLOSURE OF INVENTION

[ 0004]

(PROBLEMS TO BE SOLVED BY INVENTION)

L 0005] '

An object of the present invention is to provide a compound having an excellent control efficacy on harmful arthropods .

(MEANS TO SOLVE PROBLEMS)

[ 0006]

The present inventors have studied to find out a compound having an excellent control efficacy on harmful arthropods. As a result, they have found that an amide compound represented by the following Formula (I) has an excellent controlling effect on harmful arthropods .

Specifically, the present invention includes:

[ 1] An amide compound represented by Formula (I)

wherein

Y represents a 3-7-membered saturated heterocyclic group containing one or more atoms or groups selected from the group consisting of oxygen atom and -S(0) _t - as the heterocycle-constituting element, wherein the saturated heterocyclic group may optionally be substituted with the same or different 1 to 3 atoms or groups selected from Group D;

t represents 0, 1, or 2; X represents a phenyl group, a pyridyl group, a naphthyl group, a quinolyl group, a furyl group, a thienyl group, a benzofuranyl group, a benzothienyl group, a 3,4- methylenedioxyphenyl group, or a group represented by Formula (II) :

wherein a represents 0, 1, or 2, and A ¹ represents an oxygen atom, a sulfur atom, or -CH ₂ -, and

each of said groups for X may optionally be substituted with the same or different one or more atoms or groups selected from Group A;

represents an oxygen atom, a sulfur atom, -CH ₂ CH ₂ -, -CH2O-, -CH2S-, -CH ₂ C (CH ₃ ) 2-, -OCH2-, -SCH ₂ ^' -, or, -C(CH ₃ ) ₂ CH ₂ - r represents 0 or 1;

R ¹ , R ² , R ³ and R ⁴ are the same or different ^' to each other and each independently represent a C ₁ -C4 alkyl group which may optionally be substituted with the same or different one or more halogen atoms, a hydrogen atom, or a halogen atom;

R ⁵ and R ⁶ are the same or different to each other and each independently represent a C ₁ -C4 alkyl group which may optionally be substituted with the same or different one or more halogen atoms, a hydrogen atom, or a halogen atom;

R ⁷ and R ⁸ are the same or different to each other and each independently represent a C1-C4 alkyl group which may optionally be substituted with the same or different one or more halogen atoms, or a hydrogen atom; and

n represents 1 or 2;

Group D :

a C1-C4 alkyl group which may optionally be substituted with the same or different one or more halogen atoms,

a C1-C4 alkoxy group which may optionally be substituted with the same or different one or more halogen atoms, and

a halogen atom;

Group A:

a C1-C4 alkyl group which may. optionally be substituted with the same or different one or more halogen atoms,

a C1-C alkoxy group which may _. optionally be substituted with the same or different one or more halogen atoms,

a C1-C4 alkylthio group which may optionally be substituted with the same ^' or different one or more halogen atoms, and

a halogen atom; provided that when Y is a [ 1 , 3] dioxolan-2-yl group, X represents a pyridyl group, a naphthyl group, a quinolyl group, a furyl group, a thienyl group, a benzofuranyl group, a benzothienyl group, a 3, 4-methylenedioxyphenyl group, or a group represented by Formula (II) :

wherein a represents 0, 1, or 2, and A ¹ represents an oxygen atom, a sulfur atom, or -CH ₂ -, and

each . of said groups for X may optionally be substituted with the same or different one or more atoms or groups selected from Group A,

(hereinafter referred as to ^{1 1} the present compound' ¹ ).

[ 2] The amide compound according to [ 1] wherein is. an oxygen atom, a sulfur atom, -CH ₂ CH ₂ -, -CH ₂ 0-, -CH ₂ S-, - OCH2- or -SCH2-.

[ 3] The amide compound according to [1] or [ 2] wherein Y is a group represented by the following Formula (Il-a) or (Il-b) :

wherein

Y ¹ represents an oxygen atom or a sulfur atom; D ¹ represents an atom or group selected from Group D; m represents 0 or 1;

p represents 0, 1, or 2; and

g represents 0 or 1.

[ 4] The amide compound according to [ 3] wherein p is l or is O.

[ 5] The amide compound according to [ 3] wherein p is 2 or g is 1.

[ 6] The amide compound according to any one of [ 3] to [5] wherein Y ¹ is an oxygen atom.

[ 7] ^! The amide compound according to [ 3] wherein Y isa group represented by Formula (Il-b).

[ 8] The amide compound according to any one of [ 1] to [ 7] wherein

R ¹ is a hydrogen atom or a halogen atom;

R ² is a C1-C alkyl group which may optionally be substituted with the same or different one or more halogen atoms, or a hydrogen atom;

each of R ³ , R ⁴ ,. R ⁵ , R ⁶ and R ⁷ is a hydrogen atom;

R ⁸ is a C1-C4 alkyl group which may optionally be substituted with the same or different one or more halogen atoms, or a hydrogen atom.

[ 9] The amide compound according to any one of [ 1] to [ 8] wherein r is 0.

[ 10] An agent for controlling harmful arthropods comprising the amide compound according to any one of [ 1] to [ 9] and an inert carrier.

[ 11] A method for controlling harmful arthropods which comprises applying an effective amount of the amide compound according to any one of [ 1] to [ 9] to harmful arthropods or a place where the harmful arthropods live.

[ 12] ^■

An amide compound represented by Formula (I) :

wherein

Y represents a 3-7-membered saturated heterocyclic group containing one or more atoms or groups selected from the group consisting of oxygen atom and -S(0) _t - as the heterocycle-constituting element, wherein the saturated heterocyclic group may optionally be substituted with the same or different 1 to 3 atoms or groups selected from Group D;

t represents 0, 1, or 2;

X represents a phenyl group, a pyridyl group, a naphthyl group, a quinolyl group, a furyl group, a thienyl group, a benzofuranyl group, a benzothienyl group, a 3,4- methylenedioxyphenyl group, or a group represented by Formula (II) :

wherein a represents 0, 1, or 2, and A ¹ represents an oxygen atom, a sulfur atom, or -CH ₂ -, and

each of said groups for X. may optionally be substituted with the same or different one or more atoms or groups selected from Group A;

W represents an oxygen atom, a sulfur atom, -CH ₂ CH ₂ -, -CH ₂ O-, -CH ₂ S-, -OCH ₂ -, or -SCH ₂ -;

r represents 0 or 1;

R ¹ , R ² , R ³ and R ⁴ are the same or different to each other and each independently represent a C ₁ -C4 alkyl group which may optionally be substituted with the same or different one or more halogen atoms, a hydrogen atom, or a halogen atom;

R ⁵ and R ⁶ are the same or. different to each other and each independently represent a C ₁ -C alkyl group which may optionally be substituted with the same or different one or more halogen atoms, a hydrogen atom, or a halogen atom;

R ⁷ and R ⁸ are the same or different to each other and each independently represent a C ₁ -C4 alkyl group which may optionally be substituted with the same or different one or more halogen atoms, or a hydrogen atom; and

n represents 1 or 2; .

Group D:

a C1-C4 alkyl group which may optionally be substituted with the same or different one or more halogen atoms,

a C1-C4 alkoxy group which may optionally be substituted with the same or different one or more halogen atoms, and

a halogen atom;

Group A :

a C1-C4 alkyl group which may optionally be substituted with the same or different one or more halogen atoms ,

a C1-C4 alkoxy group which may optionally be substituted with the same or different one or more halogen atoms,

a C1-C4 alkylthio group which may optionally be substituted with the same or different one or more halogen atoms, and

a halogen atom;

provided that when Y is a [ 1,3] dioxolan-2-yl group, X represents a pyridyl group, a naphthyl group, a quinolyl group, a furyl group, a thienyl group, a benzofuranyl group, a benzothienyl group, a 3, 4-methylenedioxyphenyl group, or a group represented by Formula (II) :

wherein a represents 0, 1, or 2, and A ¹ represents an oxygen atom, a sulfur atom, or -(¾-, and

each of said groups for X may optionally be substituted with the same or different one or more atoms or groups selected from Group A. .

(EFFECT OF INVENTION)

[ 0007]

The present compound has an excellent control efficacy on harmful arthropods, thereby the present compound is useful as an active ingredient of an agent for controlling harmful arthropods.

MODE FOR CARRYING OUT THE INVENTION

[ 0008]

Isomers due to an asymmetric carbon atom, and isomers due to a double bond can be present in the present compound The present invention includes each isomer which has a control activity against harmful arthropods and an isomer mixture at any ratio of the isomers.

In the present compound, the phrase ''2-position of the carbonyl group ¹ ' as used herein refers to a position of carbon atom depicted as ' ' 2 ¹ ' in the following formula, and the phrase ''4-position of the carbonyl group ' ' refers to a position of carbon atom depicted as ^{1 1} 4 ^{1 1} in the following formula.

[ 0009]

The phrase ''a 3-7-membered saturated heterocyclic group containing one or more atoms or groups selected from the group consisting of oxygen atom and -S(0) _t - as the heterocycle-constituting element, wherein the saturated heterocyclic group may optionally be substituted with the same or different 1 to 3 atoms or groups selected from Group D' ¹ as used herein includes, for example:

a 3-7-membered saturated heterocyclic group containing one or more oxygen atoms as the heterocycle-constituting element, wherein the saturated heterocyclic group may optionally be substituted with the same or different 1 to 3 atoms or groups selected from Group D, such as an oxetan-2- yl group, an oxetan-3-yl group, a tetrahydrofuran-2-yl group, a tetrahydrofuran-3-yl group, a [ 1 , 3] dioxolan-4-yl group, a tetrahydropyran-2-yl group, a tetrahydropyran-3-yl group, a tetrahydropyran-4-yl group, a [ 1 , 3] dioxan-4-yl group, a [ 1,3] dioxan-5-^yl group, a [ 1,4] dioxan-2-yl group, an oxepan-2-yl group, an oxepan-3-yl group, an oxepan-4-yl group, a [ 1 , 3] dioxepan-4-yl group, a [ 1 , 3] dioxepan-5-yl group, a [ 1, 4] dioxepan-2-yl group, a [ 1,4] dioxepan—5-yl group, a [ 1,4] dioxepan-6-yl group, and the like;

a 3-7-membered .saturated heterocyclic group containing one or more sulfur atoms as the heterocycle-constituting element, wherein the saturated heterocyclic group may optionally be substituted with the same or different 1 to 3 atoms or groups selected from Group D, such as a thietan-2- yl group, a thietan-3-yl group, a tetrahydrothiophen-2-yl group, a tetrahydrothiophen-3-yl group, a [ 1 , 3] dithiolan-4- yl group, a tetrahydrothiopyran-2-yl group, a tetrahydrothiopyran-3-yl group, a tetrahydrothiopyran-4-yl group, a [ 1,3] dithian-4-yl group, a [ 1,3] dithian-5-yl group, a.:.[ 1,4] dithian-2-yl group, a thiepan-2-yl group, a thiepan- 3-yl group, a thiepan-4-yl group, a [ 1 , 3] dithiepan-4-yl group, a [ 1,3] dithiepan-5-yl group, a [ 1,4] dithiepan-2-yl group, a [ 1,4] dithiepan-5-yl group, a [ 1,4] dithiepan-6-yl group, and the like;

a 3-7-membered saturated heterocyclic group containing one or more -SO- as the heterocycle-constituting element, wherein the saturated heterocyclic group may optionally be substituted with the same or different 1 to 3 atoms or groups selected from Group D, such as an l-oxo-thietan-2-yl group, an l-oxo-thietan-3-yl group, an 1-oxo- tetrahydrothiophen-2-yl group, an 1-oxo-tetrahydrothiophen- 3-yl group, an l-oxo-tetrahydrothiopyran-2-yl group, an 1- oxo-tetrahydrothiopyran-3-yl group, an 1-oxo- tetrahydrothiopyran-4 -yl group, an l-oxo-thiepan-2-yl group, an l-oxo-thiepan-3-yl group, an l-oxo-thiepari-4 -yl group, and the like;

a 3-7-membered saturated heterocyclic group containing one or more -S0 ₂ - as the heterocycle-constituting element, wherein the . saturated heterocyclic group may optionally be substituted with the same or different 1 to 3 atoms or groups selected from Group D, such as a 1 , 1-dioxo-thietan- 2-yl group, a 1 , l-dioxo-thietan-3-yl group, a 1,1-dioxo- tetrahydrothiophen-2-yl group, a 1,1-dioxo- tetrahydrothiophen-3-yl group, a 1,1-dioxo- tetrahydrothiopyran-2-yl group, ^' a 1,1-dioxo- tetrahydrothiopyran-3-yl group, a 1, 1-dioxo- tetrahydrothiopyran-4 -yl group, a 1 , l-dioxo-thiepan-2-yl - group, a 1 , l-dioxo-thiepan-3-yl group, a 1 , 1-dioxo-thiepan- 4-yl group, and the like;

a 3-7-membered saturated heterocyclic group containing one or more oxygen atoms and one or more -S(0) _t ~ as the heterocycle-constituting element, wherein the saturated heterocyclic group may optionally be substituted with the same or different 1 to 3 atoms or groups selected from Group D, such as an [ 1,3] oxathietan-2-yl group, an [ 1,3] oxathiolan-2-yl group, an [ 1,3] oxathiolan-4-yl group, an [ 1,3] oxathiolan-5-yl group, an [ 1,3] oxathian-2-yl group, an [ 1, 3] oxathiolan-4-yl group, an [ 1 , 3] oxathiolan-5-yl group, an [ 1 , 4] oxathian-2-yl group, an [ 1 , 4] oxathian-3-yl group, and the like.

[ 0010]

The term ''halogen atom'' as. used herein includes, for example, fluorine atom, chlorine atom, bromine atom, and iodine atom.

The phrase ''a Ci-C ₄ alkyl group which may optionally be substituted with the same or different one or more halogen atoms' ' as used herein includes, for example, a methyl group, an ethyl group, a propyl group, an isopropyl group, a tert-butyl group, a chloromethyl group, a difluoromethyl group, a trifluoromethyl group, a trichloromethyl group, a 2 , 2 , 2-trifluoroethyl group, a 1 , 1 , 2 , 2-tetrafluoroethyl group, and a 1,1,2,2,2- pentafluoroethyl group.

The phrase ''a Ci~C alkoxy group which may optionally be substituted with the same or different one or more halogen atoms'' as used herein includes, for example, a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, a butoxy group, a difluoromethoxy group, a trifluoromethoxy -group, a trichloromethoxy group, a 2 , 2 , 2-trifluoroethoxy group, a 1 , 1 , 2 , 2-tetrafluoroethoxy group, and a 1 , 1 , 2 , 2 , 2-pentafluoroethoxy group.

The phrase ''a C ₁ -C4 alkylthio group which may optionally be substituted with the same or different one or more halogen atoms' ¹ as used herein includes, for example, a methylthio group, an ethylthio group, a propylthio group, an isopropylthio group, a butylthio group, a difluoromethylthio group, a trifluoromethylthio group, a trichloromethylthio group, a 2 , 2 , 2-trifluoroethylthio group, a 1 , 1 , 2 , 2-tetrafluoroethylthio group, and a 1,1,2,2,2- pentafluoroethylthio group.

[ 0011]

As used herein, the phrase ''a phenyl group, a pyridyl group, a naphthyl group, a quinolyl group, a furyl group, a thienyl group, a benzofuranyl group, a benzothienyl group, a 3, 4-methylenedioxyphenyl group, or a group represented by Formula ( II ) :

wherein a represents 0, 1, or 2, and A ¹ represents an oxygen atom, a sulfur atom, or -CH ₂ -, and

each of said groups may optionally be substituted the same or different one or more atoms or groups selected from Group A ¹ ' as the group represented by the X includes, for example, a phenyl group, a 3 , 4 -dichlorophenyl group, a 3-trifluoromethylphenyl group, a 3 , 5-difluorophenyl group, a 4-methoxyphenyl group, a 2-pyridyl group, a 3-pyridyl group, a 4-pyridyl group, a 1-naphthyl group, a 2-naphthyl group, a 2-quinolyl group, a 3-quinolyl group, a 4-quinolyl group, a 2-furyl group, a 3-furyl group, a 2-thienyl group, a 3-thienyl group, a 2-benzofuranyl group, a 3-benzofuranyl group, a 4-benzofuranyl group, a 5-benzofuranyl group, a 6- benzofuranyl group, a 2-benzothienyl group, a 3- benzothienyl group, a 4-benzothienyl group, a 5- benzothienyl group, a 6-benzothienyl group, a 3,4- methylenedioxyphenyl group, an 1-indanyl group, an 2- indanyl group, a 1- ( 1 , 2 , 3 , 4-tetrahydro ) naphthyl group, a 2- (1, 2, 3, 4-tetrahydro) naphthyl group, a 2-(3,4- dihydro) benzopyranyl group, a 3- (3, 4-dihydro) benzopyranyl group, a 4- (3, 4-dihydro) benzopyranyl group.

[ 0012]

The present compound includes, for example, the following compounds.

(0012-1) The compound represented by Formula (I) wherein each of R ³ , R ⁴ , R ⁵ , R ⁶ and R ⁷ is a hydrogen atom.

(0012-2) The compound represented by Formula (I) wherein each of R ³ , R ⁴ , R ⁵ , R ⁶ and R ⁷ is a hydrogen atom; and R ⁸ is a C1-C4 alkyl group which may optionally be substituted with the same or different one or more halogen atoms.

(0012-3) The compound represented by Formula (I) wherein each of R ³ , R ⁴ , R ⁵ , R ⁶ and R ⁷ is a hydrogen atom; and R ⁸ is a methyl group.

[ 0013]

(0013-1) The compound represented by Formula (I) wherein each of R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ is a hydrogen atom (0013-2) The compound represented by Formula (I) wherein each of R ¹ , R ² , R ³ , R , R ⁵ , R ⁶ , R ⁷ and R ⁸ is a hydrogen atom; the double bond at 2-position of the carbonyl group has E configuration; and the double bond at 4-position of the carbonyl group has E configuration.

[ 0014]

(0014-1) The compound represented by Formula (I) wherein each of R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ and R ⁷ is a hydrogen atom; and R ⁸ is a methyl group.

(0014-2) The compound represented by Formula (I) wherein each of R ¹ , R ² , R ³ , R , R ⁵ , R ⁶ and R ⁷ is a hydrogen atom; R ⁸ is a methyl group; the double bond at 2-position of the carbonyl group has E configuration; and the double bond at 4-position of the carbonyl group has E configuration.

[ 0015]

(0015-1) The compound represented by Formula (I) wherein each of R ¹ , R ³ , R ⁴ , R ⁵ , R ⁶ and R ⁷ is a hydrogen atom; R ² is a C1 _. -C4 alkyl group which may optionally be substituted with the same or different one or more halogen atoms; and R ⁸ is a hydrogen atom.

(0015-2) The compound represented by Formula (I) wherein each of R ¹ , R ³ , R ⁴ , R ⁵ , R ⁶ and R ⁷ is a hydrogen atom; and ^' R ² is a C1-C4 alkyl group which may optionally be substituted with the same or different one or more halogen atoms; R ⁸ is a C1-C4 alkyl group which may optionally be substituted with the same or different one or more halogen atoms.

(0015-3) The compound represented by Formula (I) wherein each of R ¹ , R ³ , R ⁴ , R ⁵ , R ⁶ and R ⁷ is a hydrogen atom; R ² is a methyl group; and R ⁸ is a hydrogen atom.

(0015-4) The compound represented by Formula (I) wherein each of R ¹ , R ³ , R ⁴ , R ⁵ , R ⁶ and R ⁷ is a hydrogen atom; R ² is a methyl group; and R ⁸ is a methyl group.

(0015-5) The compound represented by Formula (I) wherein each of R ¹ , R ³ , R ⁴ , R ⁵ , R ⁶ and R ⁷ is a hydrogen atom; R ² is a methyl group, R ⁸ is a methyl group; the double bond at 2- position of the carbonyl group has E configuration; and the double bond at 4-position of the carbonyl group has. E configuration compound.

(0015-6) The compound represented by Formula (I) wherein each of R ¹ , R ³ , R ⁴ , R ⁵ , R ⁶ and R ⁷ is a hydrogen atom; R ² is a methyl group; R ⁸ is a hydrogen atom; the double bond at 2-position of the carbonyl group has E configuration; and the double bond at 4 -position of the carbonyl group has E configuration compound.

[ 0016]

(0016-1) The compound represented by Formula (I) wherein each of R ³ , R ⁴ , R ⁵ , R ⁶ and. R ⁷ is a hydrogen atom; R ¹ is a halogen atom; . R ² is a C1-C4 alkyl . ^' group which may optionally be substituted with the same or different one or more halogen atoms; and R ⁸ is a hydrogen atom.

(0016-2) The compound represented by Formula (I) wherein each of R ³ , R ⁴ , R ⁵ , R ⁶ and R ⁷ is a hydrogen atom; R ¹ is a halogen atom; R ² is a C1-C4 alkyl group which may optionally be substituted with the same or different one or more halogen atoms; and R ⁸ is a C1-C4 alkyl group which may optionally be substituted with the same or different one or more halogen atoms.

(0016-3) The compound represented by Formula (I) wherein each of R ³ , R ⁴ , R ⁵ , R ⁶ and R ⁷ is a hydrogen atom; and R ¹ is a fluorine atom; R ² is a methyl group; and R ⁸ is a hydrogen atom.

(0016-4) The compound represented by Formula (I) wherein each- of R ³ , R ⁴ , R ⁵ , R ⁶ and R ⁷ is a hydrogen atom; R ¹ is a fluorine atom; R ² is a methyl group; and R ⁸ is a methyl group.

(0016-5) The compound represented by Formula (I) wherein each of R ³ , R ⁴ , R ⁵ , R ⁶ and R ⁷ is a hydrogen atom; R ¹ is a fluorine atom; R ² is a methyl group; and R ⁸ is a methyl group.

(0016-6) The compound represented by Formula (I) wherein each of R ³ , R ⁴ , R ⁵ , R ⁶ and R ⁷ is a hydrogen atom; R ¹ is a fluorine atom; R ² is a methyl group; R ⁸ is a methyl group; the double bond at 2-position of the carbonyl group has E configuration; and the double bond at 4-position of the carbonyl group has E configuration.

(0016-7) The compound represented by Formula (I) wherein each of R ³ , R ⁴ , R ⁵ , R ⁶ and R ⁷ is a hydrogen atom; R ¹ is a fluorine atom; R ² is a methyl group; R ⁸ is a hydrogen atom; the double bond at 2-position of the carbonyl group has E configuration; and the double bond at 4-position of the carbonyl group has E configuration.

[ 0017]

(0017-1) The compound represented ; by Formula (I) wherein Y is a 4-6-membered saturated heterocyclic group containing one or two oxygen atoms as the heterocycle-constituting element .

(0017-2) The compound represented by Formula (I) wherein Y is a 4-6-membered saturated heterocyclic group containing one oxygen atom as the heterocycle-constituting element. (0017-3) The compound represented by Formula (I) wherein Y is a 4-6-membered saturated heterocyclic group containing two oxygen atoms as the heterocycle-constituting element. (0017-4) The compound represented by Formula (I) wherein Y is a 4-6-membered saturated heterocyclic group containing one oxygen atom or one -S(0) _t ^_ as the heterocycle- constituting element.

(0017-5) The compound represented by Formula (I) wherein Y is a 4-6-membered saturated heterocyclic group containing one oxygen atom or one -S(0) _t ^_ as the heterocycle- constituting element, and t is 0.

(0017-6) The compound represented by Formula (I) wherein

Y is a tetrahydrofuran-2-yl group or a tetrahydrofuran-3-yl group;

X is a phenyl group, a pyridyl group, a naphthyl group, a 2-guinolyl group, a 2-thienyl group, a 2-benzofuranyl group, a 3 , 4 -methylenedioxyphenyl group, or a group represented by Formula (II) :

wherein a is 1 or 2, and A is an oxygen atom or -CH2-, and

each of said groups for X may optionally be substituted with the same or different one or more atoms or groups selected from the group consisting of a C1-C4 alkyl group which may optionally be substituted with the same or different one or more halogen atoms, a C1-C4 alkoxy group which . may optionally be substituted with the same or different one or more halogen atoms, and a halogen atom; r is 0 or 1;

W is ^' - CH2CH2 - , -C (CH ₃ ) 2CH2 - , - CH2O - , or -SCH ₂ -;

n is 1;

R ¹ , R ² , R ³ and R ⁴ are the same or different to each other and are each independently a C1-C4 alkyl group which may optionally be substituted with the same or different one or more halogen atoms, or a hydrogen atom;

each of R ⁵ , R ⁶ , R ⁷ and R ⁸ is a hydrogen . atom;

the double bond at 2-position of the carbonyl group has E configuration; and

the double bond at 4-position of the carbonyl group has E configuration.

[ 0018]

(0018-1) The compound represented by Formula (I) wherein Y is a group represented by Formula (Il-a) :

, Y is an oxygen atom or a sulfur atom, m is 0 or 1, and p is 0, 1, or 2;

that is, the compound represented by Formula (1-1) :

(0018-2) The compound represented by Formula (1-1) wherein Y ¹ is an oxygen atom or a sulfur atom; m is 0 or 1 ; p is 0 , 1, or 2; and D ¹ is a methyl group.

(0018-3) The compound represented by Formula (1-1) wherein Y ¹ is an oxygen atom or a sulfur atom; m is 0 or 1 ; p is 0 , 1, or 2; and D ¹ is a methyl group; and n is 1.

(0018-4) The compound represented by Formula (1-1) wherein

Y ¹ is an oxygen atom or a sulfur atom;

m is 0 or 1;

p is 0, 1, or 2;

D ¹ is a methyl group;

n is i;

each of R ¹ , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ is a hydrogen atom;

R ² is a hydrogen . atom or a methyl group;

the double bond at 2-position of the carbonyl group has E configuration; and

the double bond at 4-position of the carbonyl group has E configuration.

(0018-5) The compound represented by Formula (1-1) wherein X is a phenyl group, a 3, -dichlorophenyl group, a 3- trifluoromethylphenyl group, a 3 , 5-difluorophenyl group, a 4-methoxyphenyl group, a 2-pyridyl group, a 3-pyridyl group, a 4-pyridyl group, a 1-naphthyl group, a 2-naphthyl group, a 2-quinolyl group, a 3-quino.lyl group, a 4-quinolyl group, a 2-furyl group, a 3-furyl group, a 2-thienyl group, a 3- thienyl group, a 2-benzofuranyl group, a 2-benzothienyl group, a 3, -methylenedioxyphenyl group, an 1-indanyl group, an 2-indanyl group, a 1- (1, 2, 3, 4-tetrahydro) naphthyl group, a 2- (1, 2, 3, 4-tetrahydro) naphthyl group, a 2- (3, 4- dihydro ) benzopyranyl group, a 3- (3, 4-dihydro) benzopyranyl group, or a 4- (3, 4-dihydro) benzopyranyl group;

r .is 0 or 1;

W is an oxygen atom;

Y ¹ is an oxygen atom or a sulfur atom;

m is 0 or 1 ;

p is 0, 1, or 2;

D ¹ is a methyl group;

n is i;

each of R ¹ , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ is a hydrogen atom;

R ² is a hydrogen atom or a methyl group;

the double bond at 2-position of the carbonyl group has E configuration; and

the double bond at 4-position of the carbonyl group has E configuration. (0018-6) The · compound represented by Formula (1-1) wherein X is a phenyl group, a 3 , 4-dichlorophenyl group, a 3- trifluoromethylphenyl group, a 3 , 5-difluorophenyl group, a 4 -methoxyphenyl group, a 2-pyridyl group, a 3-pyridyl group, a 4-pyridyl group, a 1-naphthyl group, a 2-naphthyl group, a 2-quinolyl group, a 3-quinolyl group, a 4-quinolyl group, a 2-furyl group, a 3-furyl group, a 2-thienyl group, a 3- thienyl group, a 2-benzofuranyl group, a 2-benzothienyl group, a 3 , 4-methylenedioxyphenyl group, an 1-indanyl group, an 2-indanyl group, a 1- ( 1 , 2 , 3 , 4 -tetrahydro ) naphthyl group, a 2- (1, 2, 3, 4-tetrahydro) naphthyl group, a 2- (3, 4- dihydro) benzopyranyl group, a 3- (3, 4-dihydro) benzopyranyl group, or a 4 -( 3 , 4 -dihydro ) benzopyranyl group;

r is 0 ;

Y ¹ is an oxygen atom or a sulfur atom;

m is 0 or 1 ;

p is 0, 1, or 2;

D ¹ is a methyl group;

n is 1 ;

each of R ¹ , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ is a hydrogen atom;

R ² is a hydrogen atom or a methyl group;

the double bond at 2-position of the carbonyl group has E configuration; and

the double bond at 4-position of the carbonyl group has E configuration compound.

(0018-7) The compound represented by Formula (1-1) wherein X is a phenyl group, a 3 , 4 -dichlorophenyl group, a 3- trifluoromethylphenyl group, a 3 , 5-difluorophenyl group, a 4-methoxyphenyl group, a 2-pyridyl group, a 3-pyridyl group, a 4-pyridyl group, a 1-naphthyl group, a 2-naphthyl group, a 2-quinolyl group, a 3-quinolyl group, a 4-quinolyl group, a 2-furyl group, a 3-furyl group, a 2-thienyl group, a 3- thienyl group, a 2-benzofuranyl group, a 2-benzothienyl group, a 3, 4-methylenedioxyphenyl group, an 1-indanyl group, an 2-indanyl group, a 1- ( 1 , 2 , 3 , 4-tetrahydro ) naphthyl group, a 2- (1, 2, 3, 4-tetrahydro) naphthyl group, a 2- (3, 4- dihydro) benzopyranyl group, a 3- (3, 4-dihydro) benzopyranyl group, or a 4- (3, 4-dihydro) benzopyranyl group;

r is 1;

W is an oxygen atom;

Y ¹ is an oxygen atom or a sulfur atom;

m is 0 or 1;

p is 0, 1, or 2;

D ¹ is a methyl group;

n.is 1;

each of R ¹ , R ³ , R ⁴ , ⁵ , % ⁷ and R ⁸ is a hydrogen atom;

R ² is a hydrogen atom or a methyl group;

the double bond at 2-position of the carbonyl group has E configuration; and .

the double bond at. 4-position of the carbonyl group has E configuration compound.

(0018-8) The compound represented by Formula (1-1) wherein X is a phenyl group, a 2-quinolyl group, a 2-thienyl group, a 3, -methylenedioxyphenyl group, or a group represented by Formula (II) :

wherein a is 1 or 2, and A is an oxygen atom or -CH ₂ -, and

each of said groups for X may optionally be substituted with the same or different one or more atoms or groups selected from the group consisting of a Ci~C ₄ alkyl group which may optionally be substituted with the same or different one or more halogen atoms, and a halogen atom; r is 0 or 1;

W is -CH ₂ CH ₂ - or -C (CH ₃ ) ₂ CH ₂ -;

n is 1 ;

p is 1;

m is 0;

each of R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ is a hydrogen atom;

the double bond at 2-position of the carbonyl group has E configuration; and

the double bond at 4-position of the carbonyl group has E configuration compound.

(0018-9) The compound represented by Formula (1-1) wherein X is a phenyl group, a 2-quinolyl group, a 2-thienyl group, a 3, 4-methylenedioxyphenyl group, or a group represented by Formula (II):

wherein a is 1 or 2, and A ¹ is an oxygen atom or -0¾-, and

each of said groups for X may optionally be substituted with the same or different one or more atoms or groups selected from the group consisting of a C 1-C4 alkyl group which may optionally be substituted with the same or different one or more halogen atoms, and a halogen atom,-' r is O or l;

W is - CH2CH2 - , -C (CH ₃ ) 2CH2 - , -CH2O - , or ^' . - S CH2 - ;

n is 1;

P is 1;

m is 0 ;

each of R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ is a hydrogen atom;

the double bond at 2-position of the carbonyl group has E configuration; and

the double bond at 4-position of the carbonyl group has E configuration.

(0018-10) The compound represented by Formula (1-1) wherein X is a phenyl group, a pyridyl group, a naphthyl group, a 2-quinolyl group, a 2-thienyl group, a 2-benzofuranyl group, a 3 , 4-methylenedioxyphenyl group, or a group represented by Formula (II) :

wherein a is 1 or 2, and A ¹ is an oxygen atom or -CH ₂ -, and

each of said groups for X may optionally be substituted with the same or different one or more atoms or groups selected from the group consisting of a C i -C ₄ alkyl group which may optionally be substituted with the same or different one or more halogen atoms, a C1-C4 alkoxy group which may optionally be substituted with the same or different one or more halogen atoms, and a halogen atom; r is 0 or 1;

W is - CH2CH2 - , -C (CH ₃ ) 2CH2 - , - CH2O - , or -SCH ₂ -;

n is 1 ,

p is 1

m is .0 R ¹ , R ² , R ³ and R ⁴ are the same or different to each other and are each independently a C1-C4■ alkyl group which may optionally be substituted with the same or different one or more halogen atoms, or a hydrogen atom;

each of R ⁵ , R ⁶ , R ⁷ and R ⁸ is a hydrogen atom;

the double bond at ^' 2-position of the carbonyl group has E configuration; and

the double bond at 4-position of the carbonyl group has E configuration compound.

[ 0019]

(0019-1) The compound represented by Formula (I) wherein Y is a group represented by Formula (Il-a), Y ¹ is an oxygen atom, m is 0 or 1, and p is 0, 1, or 2;

that is, the compound represented by Formula (1-2) :

(0019-2) The compound represented by Formula (1-2) wherein m is 0 or 1; p is 0, 1, or 2; and D ¹ is a methyl group.

(0019-3) The compound represented by Formula (1-2) wherein m is 0 or 1; p is 0, 1, or 2; D ¹ is -a methyl group; and n is 1.

(0019-4) The compound represented by Formula (1-2) wherein m is 0 or 1; p is 0, 1, or 2;

D ¹ is a methyl group;

n is i;

each of R ¹ , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ is a hydrogen atom;

R ² is _. a hydrogen atom or a methyl group;

the double bond at 2-position of the carbonyl group has E configuration; and

the double bond at 4-position of the carbonyl group has E configuration compound.

(0019-5) The compound represented by Formula (1-2) wherein X is a phenyl group, a 3 , 4 -dichlorophenyl group, a 3- trifluoromethylphenyl group, a 3 , 5-difluorophenyl group, a 4-methoxyphenyl group, a 2-pyridyl group, a 3-pyridyl group, a 4-pyridyl group, a 1-naphthyl group, a 2-naphthyl group, a '2-quinolyl group, a 3-quinolyl group, a 4-quinolyl group, a 2-furyl group, a 3-furyl group, a 2-thienyl group, a 3- thienyl group, a 2-benzofuranyl group, a 2-benzothienyl group, a 3, 4-methylenedioxyphenyl group, an 1-indanyl group, an 2-indanyl group, a 1- (1, 2, 3, 4-tetrahydro) naphthyl group/ a 2- ( 1 , 2 , 3 , 4 -tetrahydro ) naphthyl group, a 2-(3,4- dihydro ) benzopyranyl group, a -3- (3, 4-dihydro) benzopyranyl group, or a 4- (3, 4-dihydro) benzopyranyl group;

r is 0 or 1;

W is an oxygen atom; m is 0 or 1;

p is 0, 1, or 2;

D ¹ is a methyl group;

n is i;

each of R ¹ , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ is a hydrogen atom;

R ² is a hydrogen atom or a methyl group;

the double bond at 2-position of the carbonyl group has E configuration; and

'the double bond at 4-position of the carbonyl group has E configuration. · (0019-6) The compound represented by Formula (1-2) wherein X is a phenyl group, a 3, 4-dichlorophenyl group, a 3- trifluoromethylphenyl group, a 3 , 5-difluorophenyl group, a 4-methoxyphenyl group, a 2-pyridyl group, a 3-pyridyl group, a 4-pyridyl group, a 1-naphthyl group, a 2-naphthyl group, a 2-quinolyl group, a 3-quinolyl group, a 4-quinolyl group, a 2-furyl group, a 3-furyl group, a 2-thienyl group, a 3- thienyl group, a 2-benzofuranyl group, a 2-benzothienyl group, a 3, 4-methylenedioxyphenyl group, an 1-indanyl group, an 2-indanyl group, a 1- (1, 2, 3, 4-tetrahydro) naphthyl group, a 2- (1, 2, 3, 4-tetrahydro) naphthyl group, a 2-(3,4- dihydro) benzopyranyl group, a 3- ( 3 , 4-dihydro) benzopyranyl group, or a 4- (3, 4-dihydro) benzopyranyl group;

r is 0; in is C or 1;

p is 0, 1, or 2;

D ¹ is a methyl group;

n is i; .

each of R ¹ , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ is a hydrogen atom;

R ² is a hydrogen atom or a methyl group;

the double bond at 2-position of the carbonyl group has E configuration; and

the double bond at 4-position of the carbonyl group has B configuration.

(0019-7) The compound represented by Formula (1-2) wherein X is a phenyl group, a 3, 4-dichlorophenyl group, a 3- trifluoromethylphenyl group, a 3 , 5-difluorophenyl group, a 4-methoxyphenyl group, a 2-pyridyl group, a 3-pyridyl group, a 4-pyridyl group, a 1-naphthyl group, a 2-naphthyl group, a 2-quinolyl group, a 3-quinolyl group, a 4-quinolyl group, a 2-furyl group, a 3-furyl group, a 2-thienyl group, a 3- thienyl group, a 2-benzofuranyl group, a 2-benzothienyl group, a 3, 4-methylenedioxyphenyl group, an 1-indanyl group, an 2-indanyl group, a 1- ( 1 , 2 ,3 , 4-tetrahydro ) naphthyl group, a 2- ( 1 , 2 , 3 , 4 -tetrahydro ) naphthyl group, a 2- (3, 4- dihydro ) benzopyranyl group, a 3- (3, 4-dihydro) benzopyranyl group, or a 4- (3, 4-dihydro) benzopyranyl group;

r is 1; W is an oxygen atom;

m is 0 or 1;

is 0, 1, or

D ¹ is a methyl group;

n is 1 ;

each of R ¹ , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ is a hydrogen atom;

R ² is a hydrogen atom or a methyl group;

the double bond at 2-position of the carbonyl group has E configuration; and

.the double bond at 4-position of the carbonyl group has E configuration.

(0019-8) The compound represented by Formula (1-2) wherein X is a phenyl group, a 2-quinolyl group, a 2-thienyl group, a 3, 4-methylenedioxyphenyl group, or a group represented by Formula (II) :

wherein a is 1 or 2, and A is an oxygen atom or -CH ₂ -, and

each of said groups for X may optionally be substituted with the same or different one or more atoms or groups selected from the group consisting of a C ₁ -C4 alkyl group which may optionally be substituted with the same or different one or more halogen atoms, and a halogen atom; r is 0 or 1;

W is -CH ₂ CH ₂ - or -C (CH ₃ ) ₂ CH ₂ -;

n is 1 ;

p is 1;

m is 0;

each of R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ is a hydrogen atom;

the double bond at 2-position of the carbonyl group has E configuration; and

the double bond at 4-position of the carbonyl group has E configuration.

(0019-9) The compound represented by Formula (1-2) wherein X is a . phenyl group, a 2-quinolyl group, a 2-thienyl group, a 3, 4-methylenedioxyphenyl group, or a group represented by Formula (II):

wherein a is 1. or 2, and A is an oxygen atom or -CH ₂ -, and

each of said groups for X may optionally be substituted with the same or different one or more atoms or groups selected from the group consisting of a C1-C4 alkyl group which may optionally be substituted with the same or different one or more halogen atoms, and a halogen atom; r is 0 or 1;

W is -CH2CH2- , -C (CH ₃ ) 2CH2- , -CH2O - , or -SCH ₂ -;

- n is 1;

p is 1;

m is C ;

each of R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ is a hydrogen atom;

the double bond at 2-position of the carbonyl group has E configuration; and

the double bond at 4-position of the carbonyl group has E configuration.

(0019-10) The compound represented by Formula (1-2) wherein X is a phenyl group, a pyridyl group, a naphthyl group, a 2-quinolyl group, a 2-thienyl group, a 2-benzofuranyl group, a 3 , 4 -methylenedioxyphenyl group, or a group represented by Formula (II) :

wherein a is 1 or 2, and A ¹ is an oxygen atom or -CH2 - , and

each of said groups for X may optionally be substituted with the same or different one or more atoms or groups selected from the group consisting of a C 1-C4 alkyl group which may optionally be substituted with the same or different one or more halogen atoms, a C1-C4 alkoxy group which may optionally be substituted with the same or different one or more halogen atoms, and a halogen atom; r is 0 or 1 ;

W is - CH2CH2 - , -C (CH ₃ ) 2CH2 - , -CH2O - , or -SCH ₂ -;

n is 1;

p is 1,- rn is 0 ;

R ¹ , R ² , R ³ and R ⁴ are the same or different to each other and are each independently a C i - C ₄ alkyl group which may optionally be substituted with the same or different one or more halogen atoms, or a hydrogen atom;

each of R ⁵ , R ⁶ , R ⁷ and R ⁸ is a. hydrogen atom;

the double bond at 2-position of the carbonyl group has E configuration; and

the double bond at 4-position of the carbonyl group has E configuration compound.

[ 0020]

(0020-1) The compound represented by Formula (I) wherein Y is an oxetan-2-yl group or an oxetan-3-yl group, each of which may optionally be substituted with one atom or group .selected from Group D (i.e., Y is a group represented by Formula (Il-a) wherein Y ¹ is an oxygen atom, and p is 0); that is, the compound represented by Formula (1-3) :

(0020-2) The compound represented by Formula (1-3) wherein m is 0 or 1; and D ¹ is a methyl group.

(0020-3) The compound represented by Formula (1-3) wherein m is 0 or 1; D ¹ is a methyl group; and n is 1.

(0020-4) The compound represented . by Formula (1-3) wherein m is 0 or 1;

D ¹ . is a methyl group;

n is i;

each of R ¹ , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ is a hydrogen atom;

R ² is a hydrogen atom or a methyl group;

the double bond at 2-position of the carbonyl group has E configuration; and

the double bond at 4-position of the carbonyl group has E configuration.

(0020-5) The compound represented by Formula (1-3) wherein X is a phenyl group, a 3, 4-dichlorophenyl group, a 3- trifluoromethylphenyl group, a 3 , 5-difluorophenyl group, a 4-methoxyphenyl group, a 2-pyridyl group, a 3-pyridyl group, a 4-pyridyl group, a 1-naphthyl group, a 2-naphthyl group, a 2-quinolyl group, a 3-quinolyl group, a 4-quinolyl group, a 2-furyl group, a 3-furyl group, a 2-thienyl group, a 3- thienyl group,-, a 2-benzofuranyl group, a 2-benzothienyl group, a 3, 4-methylenedioxyphenyl group, an 1-indanyl group, an 2-indanyl group, a 1- ( 1 , 2 , 3 , 4-tetrahydro) naphthyl group, a 2- ( 1 , 2 , 3 , 4-tetrahydro) naphthyl group, a 2-(3,4- dihydro) benzopyranyl group, a 3- (3, 4-dihydro) benzopyranyl group, or a 4- (3, 4-dihydro) benzopyranyl group;

r is 0 or 1;

W is. an oxygen atom;

m is 0 or 1;

D ¹ is a methyl group;

n is ^' 1;

each of R ¹ , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ is a hydrogen atom;

R ² is a hydrogen atom or a methyl group;

the double bond at 2-position of the. carbonyl group has E configuration; and

the double bond at 4-position of the carbonyl group has E configuration.

(0020-6) The compound represented by Formula (1-3) wherein X is a phenyl group, a 3, 4-dichlorophenyl group, a 3- trifluoromethylphenyl group, a 3 , 5-difluorophenyl group, a 4-methoxyphenyl group, a 2-pyridyl group, a 3-pyridyl group, a 4-pyridyl group, a 1-naphthyl group, a 2-naphthyl group, a 2-quinolyl group, a 3-quinolyl group, a 4-quinolyl group, a 2-furyl group, a 3-furyl group, a 2-thienyl group, a 3- thienyl group, a 2-benzofuranyl group, a 2-benzothienyl group, a 3, 4-methylenedioxyphenyl group, an 1-indanyl group, an 2-indanyl group, a 1- ( 1 , 2 , 3 , 4 -tetrahydro) naphthyl group, a 2- (1, 2, 3, 4-tetrahydro) naphthyl group, a 2-(3,4- dihydro) benzopyranyl group, a 3- ( 3 , -dihydro) benzopyranyl group, or a 4- (3, 4-dihydro) benzopyranyl group;

r is 0 ;

m is 0 or 1;

D ¹ is a methyl group;

n is 1 ;

each of R ¹ , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ is a hydrogen atom;

R ² is a hydrogen atom or a methyl group;

the double bond at 2-position of the carbonyl group has E configuration; and

the double bond at 4-position of the carbonyl group has E configuration.

(0020-7) The compound represented by Formula (1-3) wherein X is a phenyl group, a 3, 4-dichlorophenyl group, a 3- trifluoromethylphenyl group, a 3 , 5-difluorophenyl group, a 4-methoxyphenyl group, a 2-pyridyl group, a 3-pyridyl group, a 4-pyridyl group, a 1-naphthyl group, a 2-naphthyl group, a 2-guinolyl group, a 3-quinolyl group, a 4-quinolyl group, a 2-furyl group, a 3-furyl group, a 2-thienyl group, a 3- thienyl group, a 2-benzofuranyl group, a 2-benzothienyl group, a 3 , 4-methylenedioxyphenyl group, an 1-indanyl group, an 2-indanyl group, a 1- ( 1 , 2 , 3 , 4 -tetrahydro ) naphthyl group, a 2- ( 1 , 2 , 3 , 4-tetrahydro ) naphthyl group, a 2- (3, - dihydro ) benzopyranyl group, a 3- (3, -dihydro) benzopyranyl group, or a 4- (3, 4-dihydro) benzopyranyl group;

r is 1 ;

W is an oxygen atom;

m is 0 or 1;

D ¹ is a methyl group;

n is 1 ;

each of R ¹ , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ is a hydrogen atom;

R ² is a hydrogen atom or a methyl group;

the double bond at 2-position of the carbonyl group has E configuration; and

the double bond at 4-position of the carbonyl group has E configuration.

(0020-8) The compound represented by Formula (1-3) wherein X is a phenyl group, a 2-quinolyl group, a 2-thienyl group, a 3, 4-methylenedioxyphenyl group, or a group represented by Formula (II) :

(Π)

wherein a is 1 or 2, and A ¹ is an oxygen atom or -CH2 - , and

each of said groups for X may optionally be substituted . with the same or different one or more atoms or groups selected from the group consisting of a C 1-C4 alkyl group which may optionally be substituted with the same or different one or more halogen atoms, and a halogen atom; r is 0 or 1;

W is - CH2CH2- or -C (CH ₃ ) 2CH2- ;

n is 1 ;

m is 0 ;

each of R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ is a hydrogen atom;

the double bond at 2-position of the carbonyl group has E configuration; and

the double bond at 4-position of the carbonyl group has E configuration.

(0020-9) The compound represented by Formula (1-3) wherein X is a phenyl group, a 2-quinolyl group, a 2-thienyl group, a 3, 4-methylenedioxyphenyl group, or a group represented by Formula (II):

wherein a is 1 or 2, and A ¹ is an oxygen atom or -CH ₂ -, and

each of said groups for X may optionally be substituted with the same or different one or more atoms or groups selected from the group consisting of a C 1-C4 alkyl group which may optionally be substituted with the same or different one or more halogen atoms, and a halogen atom; r is 0 or 1;

W is -CH2CH2 - , -C (CH ₃ ) 2CH2 - , -CH2O - , or -SCH ₂ -;

n is 1 ;

p is 1;

m is 0 ;

each of R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ is a hydrogen atom;

the double bond at 2-position of the carbonyl group has E configuration; and

the double bond at 4-position of the carbonyl group has E configuration.

[ 0021]

(0021-1) The compound represented by Formula (I) wherein Y is an oxetan-3-yl group which may optionaly be substituted with one atom or group selected from Group D at 3-position of the oxetane (i.e., Y is a group represented by Formula (Il-a) wherein Y ¹ is an oxygen atom, p is 0, m is 0 or 1, D ¹ is attached to 3-position of the oxetane when m is 1, and the carbon to which R ⁷ and R ⁸ are atached is attached to 3-position of the oxetane) ;

that is, the compound represented by Formula (1-4) :

(0021-2) The compound represented by Formula (1-4) wherein m is 0 or 1; and D ¹ is a methyl group.

(0021-3) The compound represented by Formula (1-4) wherein m is 0 or 1; D ¹ is a methyl group; and n is 1.

(0021-4) The compound represented by Formula (1-4) wherein m is 0 or 1;

D ¹ is a methyl group;

n is 1 ;

each of R ¹ , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ is a hydrogen atom;

R ² is a hydrogen atom or a methyl group;

the double bond at 2-position of the carbonyl group has E configuration; and

the double bond at 4-position of the carbonyl group has E configuration.

(0021-5) The compound represented by Formula (1-4) wherein X is a phenyl group, a 3, 4-dichlorophenyl group, a 3- trifluoromethylphenyl group, a 3, 5-difluorophenyl group, a -methoxyphenyl group, a 2-pyridyl group, a 3-pyridyl group, a 4-pyridyl group, a 1-naphthyl group, a 2-naphthyl group, a 2-quinolyl group, a 3-quinolyl group, a 4-quinolyl group, a 2-furyl group, a 3-furyl group, a 2-thienyl group, a 3- thienyl group, a 2-benzofuranyl group, a 2-benzothienyl group, a 3 , 4 -methylenedioxyphenyl group, an 1-indanyl group, an 2-indanyl group, a 1- (1, 2, 3, 4-tetrahydro) naphthyl group, a 2- (1, 2, 3, 4-tetrahydro) naphthyl group, a 2- (3, 4- dihydro) benzopyranyl group, a 3- ( 3 , 4 -dihydro) benzopyranyl group, or a 4- (3, 4-dihydro) benzopyranyl group;

r is 0 or 1;

W is an oxygen atom;

m is 0 or 1 ;

D ¹ is a methyl■ group;

n is i;

each of R ¹ , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ is a hydrogen atom;

R ² is a hydrogen atom or a methyl group;

the double bond at 2-position of the carbonyl group has E configuration; and

the double bond at 4-position of the carbonyl group has E configuration. ·

(0021-6) The compound represented by Formula (1-4) wherein X is a phenyl group, a 3, 4-dichlorophenyl group, a 3- trifluoromethylphenyl group, a 3 , 5-difluorophenyl group, a 4-methoxyphenyl group, a 2-pyridyl group, a 3-pyridyl group, a 4-pyridyl group, a 1-naphthyl group, a 2-naphthyl group, a 2-guinolyl group, a 3-quinolyl group, a 4-quinolyl group, a 2-furyl group, a 3-furyl group, a 2-thienyl group, a 3- thienyl group, a 2-benzofuranyl group, a 2-benzothienyl group, a 3, 4-methylenedioxyphenyl group, an 1-indanyl group, an 2-indanyl group, a 1- (1, 2, 3, 4-tetrahydro) naphthyl group, a 2- (1, 2, 3, -tetrahydro) naphthyl group, a 2- (3, 4- dihydro ) benzopyranyl group, a 3- (3, 4-dihydro) benzopyranyl group, or a 4- ( 3 , 4-dihydro ) benzopyranyl group;

r is 0;

m is 0 or 1;

D ¹ is a methyl group;

n is.1;

each of R ¹ , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ is a hydrogen atom;

R ^2' is a hydrogen atom or a methyl group;

the double bond at 2-position of the carbonyl group has E configuration; and

the double bond at 4-position of the carbonyl group has E configuration.

(0021-7) The compound represented by Formula (1-4) wherein X is a phenyl group, a 3, 4-dichlorophenyl group, a 3- trifluoromethylphenyl group, a 3 , 5-difluorophenyl group, a 4-methoxyphenyl group, a 2-pyridyl group, a 3-pyridyl group, a 4-pyridyl group, a 1-naphthyl group, a 2-naphthyl group, a 2-quinolyl group, a 3-quinolyl group, a 4-quinolyl group, a 2-furyl group, a 3-furyl group, a 2-thienyl group, a 3- thienyl group, a 2-benzofuranyl group, a 2-benzothienyl group, a 3 , 4 -methylenedioxyphenyl group, an 1-indartyl group, an 2-indanyl group, a 1- ( 1 , 2 , 3 , 4-tetrahydro ) naphthyl group, a 2- ( 1 , 2 , 3 , 4-tetrahydro ) naphthyl group, a 2- (3, 4- dihydro ) benzopyranyl group, a 3- (3, 4-dihydro) benzopyranyl group, or a 4- (3, 4-dihydro) benzopyranyl group;

r is 1 ;

W is an oxygen atom;

m is 0 or 1;

D ¹ is a methyl group;

is i;

each of R ¹ , R ³ , R ⁴ , . R ⁵ , _. R ⁶ , R ⁷ and R ⁸ is a hydrogen atom;

R ² is a hydrogen atom or a methyl group;

the double bond at 2-position of the carbonyl group has E configuration; and

the double bond at 4-position of the carbonyl group has E configuration.

(0021-8) The compound represented by Formula (1-4) wherein X is a phenyl group, a 2-quinolyl group, a 2-thienyl group, a 3 , 4 -methylenedioxyphenyl group, or a group represented by Formula (II) :

wherein a is 1 or 2,. and A ¹ is an oxygen atom or -CH ₂ -, and

each of said groups for X may optionally be substituted with the same or different one or more atoms or groups selected from the group consisting of a C1-C4 alkyl group which may optionally be substituted with the same or different one or more halogen atoms, and a halogen atom; r is 0 or 1;'

W is -CH ₂ CH ₂ - or -C(CH ₃ ) ₂ CH ₂ -;

n is i; .

m is 0 ;

each of R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ is a hydrogen atom;

the double bond at 2-position of the carbonyl group has E configuration; and

the double bond at -position of the carbonyl group has E configuration.

(0021-9) The compound represented by Formula (1-4) wherein X is a phenyl group, a 2-quinolyl group, a 2-thienyl group, a 3, 4-methylenedioxyphenyl group, or a group represented by Formula (II):

wherein a is 1 or 2, and A ¹ is an oxygen atom or -0¾-, and

each of said groups for X may optionally be substituted with the same or different one or more atoms or groups selected from the group consisting of a C 1-C4 alkyl group which may optionally be substituted with the same or different one or. more halogen atoms, and a halogen atom; r is 0 or 1;

is - CH2CH2 - , -C (CH ₃ ) 2CH2 - , -CH2O - , or -SCH ₂ -;

n is 1 ;

p. is 1;

m is 0 ;

each of R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ is a hydrogen atom;

the double bond at 2-position of the carbonyl group has E configuration; and

the double bond at 4-position of the carbonyl group has E configuration.

[ 0022]

(0022-1) The compound represented by Formula (I) wherein Y is a tetrahydrofuran-2-yl group or a tetrahydrofuran-3-yl group, each of which may optionally be substituted with one atom or group selected from Group D (i.e., Y is a group represented by Formula (Il-a) wherein Y ¹ is an oxygen atom, and p is 1 ) ;

that is, the compound represented by Formula (1-5) :

(0022-2) The compound represented by Formula (1-5) wherein m is 0 or 1; and D ¹ is a methyl group.

(0022-3) The compound represented by Formula (1-5) wherein m is 0 or 1; D ¹ is a methyl group; and n is 1.

(0022-4) The compound represented by Formula (1-5) wherein m is 0 or 1;

D ¹ is a methyl group;

n is 1 ;

each of R ¹ , R ³ , R ⁴ , R ⁵ , R ⁶ , ^' R ⁷ and R ⁸ is a hydrogen atom;

R ² is a hydrogen atom or a methyl group;

the double bond at 2-position of the carbonyl group has E configuration; and

the. double bond at 4-position of the carbonyl group has E configuration.

(0022-5) The compound represented by Formula (1-5) wherein X is a phenyl group, a 3 , 4-dichlor phenyl group, a 3- trifluoromethylphenyl group, a 3 , 5-difluorophenyl group, a 4-methoxyphenyl group, a 2-pyridyl group, a 3-pyridyl group, a 4-pyridyl group, a l-naphthyl group, a 2-naphthyl group, a 2-quinolyl group, a 3-quinolyl group, a 4-quinolyl group, a 2-furyl group, a 3-furyl group, a 2-thienyl group, a 3- thienyl group, a 2-benzofuranyl group, a 2-benzothienyl group, a 3, 4-methylenedioxyphenyl group, an 1-indanyl group, an 2-indanyl group, a 1- (1, 2, 3, 4-tetrahydro) naphthyl group, a 2- (1, 2, 3, 4-tetrahydro) naphthyl group, a 2- (3, 4- dihydro) benzopyranyl group, a 3-.(3, 4-dihydro) benzopyranyl group, or a 4- (3, 4-dihydro) benzopyranyl group;

r is 0 or 1;

W is an oxygen atom;

m is 0 or 1;

D ¹ is a methyl group;

n is 1;

each of R ¹ , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ is a hydrogen atom;

R ² is a hydrogen atom or a methyl group;

the double bond at 2-position of the carbonyl group has E configuration; and

the double bond at 4-position of the carbonyl group has E configuration.

(0022-6) The compound represented by Formula (1-5) wherein X is a phenyl group, a 3, 4-dichlorophenyl group, a 3- trifluoromethylphenyl group, a 3 , 5-difluorophenyl group, a 4-methoxyphenyl group, a 2-pyridyl group, a 3-pyridyl group, a 4-pyridyl group, a 1-naphthyl group, a 2-naphthyl group, a 2-quinolyl group, a 3-quinolyl group, a 4-quinolyl group, a 2-furyl group, a 3-furyl group, a 2-thienyl group, a 3- thienyl group, a 2-benzofuranyl group, a 2-benzothienyl group, a 3, -methylenedioxyphenyl group, an 1-indanyl group, an 2-indanyl group, a 1- (1, 2, 3, 4-tetrahydro) naphthyl group, a 2- ( 1 , 2 , 3 , 4-tetrahydro) naphthyl group, a 2-(3,4- dihydro ) benzopyranyl group, a 3-,(3, 4-dihydro) benzopyranyl group, or a 4- (3, 4-dihydro) benzopyranyl group;

r is 0 ;

m is 0 or 1;

D ¹ is a methyl group;

n is i;

each of R ¹ , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ is a hydrogen atom;

R ² is a hydrogen atom or a methyl group;

the double bond at 2-position of the carbonyl group has E configuration; and

the double bond at 4-position of the carbonyl group has E configuration.

(0.022-7) The compound represented by Formula (1-5) wherein X is a phenyl group, a 3 , 4 -dichlorophenyl group, a 3- trifluoromethylphenyl group, a 3 , 5-difluorophenyl group, a 4-methoxyphenyl group, a 2-pyridyl group,, a 3-pyridyl group, a 4-pyridyl group, a 1-naphthyl group, a 2-naphthyl group, a 2-quinolyl group, a 3-quinolyl group, a 4-quinolyl group, a 2-furyl group, a 3-furyl group, a 2-thienyl group, a 3- thienyl group, a 2-benzofuranyl group, a 2-benzothienyl group, a 3, 4-methylenedioxyphenyl group, an 1-indanyl. group, an 2-indanyl group, a 1- ( 1 , 2 , 3 , 4 -tetrahydro ) naphthyl group, a 2- (1, 2, 3, -tetrahydro) naphthyl group, a 2-(3,4- dihydro) benzopyranyl group, a 3- (3, 4-dihydro) benzopyranyl group, or a 4- (3, 4-dihydro) benzopyranyl group;

r is 1 ; ^■

W is an oxygen atom;

m is 0 or 1;

D ¹ is a methyl group;

n is 1;

each of R ¹ , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ is a hydrogen atom;

R ² is a hydrogen atom or a methyl group;

the double bond at 2-position of the carbonyl group has E configuration; and

the double bond at 4-position of the carbonyl group has E configuration.

(0022-8) The compound represented by Formula (1-5) wherein X is a phenyl group, a 2-quinolyl group, a 2-thienyl group, a 3, 4-methylenedioxyphenyl group, or a group represented by Formula (II) :

wherein a is 1 or 2, and A is an oxygen atom or -CH ₂ -, and

each of said groups for X may optionally be substituted with the same or different one or more atoms or groups selected from the group consisting of a C1-C4 alkyl group which may optionally be substituted with the same or different one or more halogen atoms, and a halogen atom; r is 0 or 1;

W is -CH2CH2- or -C (CH ₃ ) 2CH2-;

n is i;

m is 0 ;

each of R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ is a hydrogen atom;

the double bond at 2-position of the carbonyl group has E configuration; and

the double bond at 4-position of the carbonyl group has E configuration.

(0022-9) The compound represented by Formula (1-5) wherein X is a phenyl group, a 2-quinolyl group, a 2-thienyl group, a 3, 4-methylenedioxyphenyl group, or a group represented by Formula (II) :

wherein a is 1 or 2, and A is an oxygen atom or - CH2 - , and

each of said groups for X may optionally . be substituted with the same or different one or more atoms or groups selected from the group consisting of a C 1-C4 alkyl group which may optionally be substituted with the same or different one or more halogen atoms, and a halogen atom; r is 0 or 1 ;

W is -CH2CH2- , -C (CH ₃ ) 2CH2 - , -CH2O - , or -SCH ₂ -;

n is 1;

p is 1;

m is 0 ;

each of R ¹ , R ² , R ³ ,. R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ is a hydrogen atom;

the double bond at 2-position of the carbonyl group has E configuration; and

the double bond at 4-position of the carbonyl group has E configuration.

[ 0023]

(0023-1) The compound represented by Formula (I) wherein Y is a tetrahydrofuran-2-yl group which may optionally be substituted with one atom or group selected from Group D at 2-position of the tetrahydrofuran (i.e., Y is a group represented by Formula (Il-a) wherein Y ¹ is an oxygen atom, p is 1, m is 0 or 1, D ¹ is attached to 2-position of the tetrahydrofuran when m is 1, and the carbon to which R ⁷ and R ⁸ . are atached is attached to 2-position of the tetrahydrofuran) ,

that is, the compound represented by Formula (1-6)

(0023-2) The compound represented by Formula (1-6) wherein m is 0 or 1; and D ¹ is a methyl group.

(0023-3) The compound represented by Formula (1-6) wherein m is 0 or 1; D ¹ is a methyl group; and n is 1.

(0023-4) The compound represented by Formula (1-6) wherein m is 0 or 1;

D ¹ is a methyl group;

n is i;

each of R ¹ , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ is a hydrogen atom;

R ² is a hydrogen atom or a methyl group;

the double bond at 2-position of the carbonyl group has E configuration;, and

the double bond at 4-position of the carbonyl group has E configuration.

(0023-5) The compound represented by Formula (1-6) wherein

X is a phenyl group, a 3, 4-dichlorophenyl group, a 3- trifluoromethylphenyl group, a 3 , 5-difluorophenyl group, a 4-methoxyphenyl group, a 2-pyridyl group, a 3-pyridyl group, a 4-pyridyl group, a 1-naphthyl group, a 2-naphthyl group,, a 2-quinolyl group, a 3-quinolyl group, . a■ -quinolyl group, a 2-furyl group, a 3-furyl group, a 2-thienyl group, a 3- thienyl group, a 2-benzofuranyl group, a 2-benzothienyl group, a 3 , 4-methylenedioxyphenyl group, an 1-indanyl group, an 2-indanyl group, a 1- ( 1 , 2 , 3 , 4-tetrahydro ) naphthyl group, a 2- ( 1 , 2 , 3 , 4-tetrahydro ) naphthyl group, a 2-(3,4- dihydro) benzopyranyl group, a 3- (3, 4-dihydro) benzopyranyl group, or a 4- (3, 4-dihydro) benzopyranyl group;

r is 0 or 1;

W is an oxygen atom;

m is 0 or 1;

D ¹ is a methyl group;

n is 1;

each of R ¹ , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ is a hydrogen atom;

R ² -. is a hydrogen atom or a methyl group;

the double bond at 2-position of the carbonyl group has E configuration; and

the double bond at 4-position of the carbonyl group has E configuration.

(0023-6) The compound represented by Formula (1-6) wherein

X is a phenyl group, a 3 , -dichlorophenyl group, a 3- trifluoromethylphenyl group, a 3 , 5-difluorophenyl group, a 4-methoxyphenyl group, a 2-pyridyl group, a 3-pyridyl group, a 4-pyridyl group, a 1-naphthyl group, a 2-naphthyl group, a 2-quinolyl group, a 3-quinolyl group, a 4-quinolyl group, a 2-furyl group, a 3-furyl group, a 2-thienyl group, a 3- thienyl group, a 2-benzofuranyl group, a 2-benzothienyl group, a 3, -methylenedioxyphenyl group, an 1-indanyl group, an 2-indanyl group, a 1- ( 1 , 2 , 3 , 4-tetrahydro ) naphthyl group, a 2- (1, 2, 3, 4-tetrahydro) naphthyl group, a 2-(3,4- dihydro) benzopyranyl group, a 3- (3, 4-dihydro) benzopyranyl group, or a 4- (3, 4-dihydro) benzopyranyl group;

r is 0;

m is 0 or 1;

D ¹ is a methyl group;

n is 1 ;

each of R ¹ , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ is a hydrogen atom;

R ² is a hydrogen atom or a methyl group;

the double bond at 2-position of the carbonyl group has E configuration; and

the double bond at 4-position of the carbonyl group has E configuration. (0023"7) The compound represented by Formula (1-6) wherein X is a phenyl group, a 3, -dichlorophenyl group, a 3- trifluoromethylphenyl group, a 3 , 5-difluorophenyl group, a 4-methoxyphenyl group, a 2-pyridyl group, a 3-pyridyl group, a 4-pyridyl group, a 1-naphthyl group, a 2-naphthyl group, a 2-quinolyl group, a 3-quinolyl group, a 4-quinolyl group, a 2-furyl group, a 3-furyl group, a 2-thienyl group, a 3- thienyl group, a 2-benzofuranyl group, a. 2-benzothienyl group, a 3 , 4 -methylenedioxyphenyl group, an 1-indanyl group, an 2-indanyl group, a 1- ( 1 , 2 , 3 , 4-tetrahydro ) naphthyl group, a 2- (1, 2, 3, 4-tetrahydro) naphthyl group, a 2- (3, 4- dihydro) benzopyranyl group, a 3- (3, 4-dihydro) benzopyranyl group, or a 4- (3, 4-dihydro) benzopyranyl group;

r is 1;

W is an oxygen atom;

m is 0 or 1;

D ¹ is a methyl group;

n is i;

each of R ¹ , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ is a hydrogen atom;

R ² is a hydrogen atom or a methyl group;

the double bond at 2-position of the carbonyl group has E configuration; and

the ^' double bond at 4-position of the carbonyl group has E configuration. (0023-8) The compound represented by Formula (1-6) wherein X is a phenyl group, a 2-quinolyl group, a 2-thienyl group, a 3, 4-methylenedioxyphenyl group, or a group represented by Formula (II) :

wherein a is 1 or 2, and A ¹ is an oxygen atom or -CH ₂ -, and

each of said groups for X may optionally be substituted with the same or different one or more atoms or groups selected from the group consisting of a C1-C4 alkyl ^• group which may optionally be substituted with the same or different one or more halogen atoms, and a halogen atom; r is 0 or 1;

W is -CH ₂ CH ₂ - or -C ( CH ₃ ) ₂ CH ₂ - ;

n is 1 ;

m is 0 ;

each of R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ is a hydrogen atom;

the double bond at 2-position of the carbonyl group has E configuration; and

the double bond at 4-position of the carbonyl group has E configuration.

(0023-9) The compound represented by Formula (1-6) wherein X is a phenyl group, a 2-quinolyl group, a 2-thienyl group, a 3 , 4-methylenedioxyphenyl group, or a group represented by Formula (II) :

wherein a is 1 or 2, and A ¹ is an oxygen .atom or -(¾- and

each of said groups for X may optionally be substituted with the same or different one or more atoms or groups selected from the group consisting of a C 1-C4 alkyl group which may optionally be substituted with the same or different one or more halogen atoms, and a halogen atom; r is 0 or 1;

W is - CH2CH2 - , -C (CH ₃ ) 2CH2 - , - CH2O - , or -SCH ₂ -;

n is i;

p is 1;

m is 0 ;

each of R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ is a hydrogen atom;

the double bond at 2-position of the carbonyl group has E configuration; and

the double bond at 4-position of the carbonyl group has E configuration.

(0023-10) The compound represented by Formula (1-6) wherein X is a phenyl group, a pyridyl group, a naphthyl group, a 2-quinolyl group, a 2-thienyl group, a 2-benzofuranyl group, a 3, -methylenedioxyphenyl group, or a group represented by Formula (II) :

wherein a is 1 or 2, and A ¹ is an oxygen atom or -CH ₂ -, and

each of said groups for X may optionally . be substituted with the' same or different one or more atoms or groups selected from the group consisting of a C 1-C4 alkyl group which may optionally be substituted with the same or different one or more halogen atoms, a C1-C4 alkoxy group which may optionally be substituted with the same or different one or more -halogen atoms, and a halogen atom; r is 0 or 1;

W is - CH2CH2 - , -C (CH ₃ ) 2CH2 - , - CH2O - , or -SCH ₂ -;

n is 1 ;

P is 1 ;

m is 0 ;

R ¹ , R ² , R ³ , and R ⁴ are the same or different to each other and are each independently a C 1-C4 alkyl group which may optionally be substituted with the same or different one or more halogen atoms, or a hydrogen atom; each of R ⁵ , R ⁶ , R ⁷ and R ⁸ is a hydrogen atom;

the double bond at 2-position of the carbonyl group has E configuration; and

the double bond at 4-position of the carbonyl group has E configuration.

[ 0024]

(0024-1) The compound represented by. Formula (I) wherein Y is a tetrahydrofuran-3-yl group which may optionally be substituted with one atom or group selected from Group D at 3-position of · the tetrahydrofuran (i.e., Y is a group represented by Formula (Il-a) ¹ wherein Y ¹ is an oxygen atom, p is 1, m is 0 or 1, D ¹ is attached to 3-position of the tetrahydrofuran when m is 1, and the carbon to which R ⁷ and R ⁸ are atached is attached to 3-position of the tetrahydrofuran) ;

that is, the compound represented by Formula (1-7) :

(0024-2) The compound represented by Formula (1-7) wherein m is 0 or 1; and D ¹ is a methyl group.

(0024-3) The compound represented by Formula (1-7) wherein m is 0 or 1; D ¹ is a methyl group; and n is 1.

(0024-4) The compound represented by Formula (1-7) wherein m is 0 or 1;

D ¹ is a methyl group;

n is 1 ;

each of R ¹ , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ is a hydrogen atom;

R ² is a hydrogen atom or a methyl group;

the double bond at 2-position of the carbonyl group has E configuration; and

the double bond at 4-position of the carbonyl group has E configuration.

(0024-5) The compound represented by Formula (1-7) wherein X is a phenyl group, a 3 , -dichlorophenyl group, a 3- trifluoromethylphenyl group, a 3 , 5-difluorophenyl group, a 4-methoxyphenyl group, a 2-pyridyl group, a 3-pyridyl group, a 4-pyridyl group, a 1-naphthyl group, a 2-naphthyl group, a 2-guinolyl group, a 3-quinolyl group, a 4-quinolyl group, a 2-furyl group, a 3-furyl group, a 2-thienyl group, a 3- thienyl group, a 2-benzofuranyl group, a 2-benzothienyl group, a 3, -methylenedioxyphenyl group, an 1-indanyl group, an 2-indanyl group, a 1- ( 1 , 2 , 3 , 4 -tetrahydro ) naphthyl group, a 2- (1, 2, 3, 4-tetrahydro) naphthyl group, a 2-(3,4- dihydro) benzopyranyl group, a 3- (3, 4-dihydro) benzopyranyl group, or a 4- (3, 4-dihydro) benzopyranyl group;

r is 0 or 1;

W is an oxygen atom; m is 0 or 1;

D ¹ is a methyl group;

n is i;

each of R ¹ , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ is a hydrogen atom;

R ² is a hydrogen atom or a methyl group;

the double bond at 2-position of the carbonyl group has E configuration; and

the double bond at 4-position of the carbonyl group has E configuration.

(0024-6) The compound represented by Formula (1-7) wherein X is a phenyl group, a 3 , 4 -dichlorophenyl group, a 3- trifluoromethylphenyl group, a 3 , 5-difluorophenyl group, a 4-met.hoxyphenyl group, a 2-pyridyl group, a 3-pyridyl group, a 4-pyridyl group, a 1-naphthyl group, a 2-naphthyl group, a 2-quinolyl group, a 3-quinolyl group, a 4-quinolyl group, a .2-furyl group, a 3-furyl group, a 2-thienyl group, a 3- thienyl group, a 2-benzofuranyl group, a 2-benzothienyl group, a 3, -methylenedioxyphenyl group, an 1-indanyl group, an 2-indanyl group, a 1- ( 1, 2, 3, 4-tetrahydro) naphthyl group, a 2- (1, 2, 3, 4-tetrahydro) naphthyl group, a 2-(3,4- dihydro ) benzopyranyl group, a 3- (3, 4-dihydro) benzopyranyl group, or a 4- (3, 4-dihydro) benzopyranyl group;

r is 0 ;

m is 0 or 1; D ¹ is a methyl group;

n is 1;

each of R ¹ , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ is a hydrogen atom;

R ² is a hydrogen atom or a methyl group;

the double bond at 2-position of the carbonyl group has E configuration; and

the double bond at 4-position of the carbonyl group has E configuration.

(0024-7) The compound represented by Formula (1-7) wherein X is a phenyl group, a 3 , 4 -dichlorophenyl group, a 3- trifluoromethylphenyl group, a 3 , 5-difluorophenyl group, a 4-methoxyphenyl group, a 2-pyridyl group, a 3-pyridyl group, a 4-pyridyl group, a 1-naphthyl group, a 2-naphthyl group, a 2-quinolyl group, a 3-quinolyl group, a 4-quinolyl group, a 2-furyl group, a 3-furyl group, a 2-thienyl group, a 3- thienyl group, a 2-benzofuranyl group, a 2-benzothienyl group, a 3, 4-methylenedioxyphenyl group, an 1-indanyl group, an 2-indanyl group, a 1- ( 1 , 2 , 3 , 4-tetrahydro ) naphthyl group, a 2- (1, 2, 3, 4-tetrahydro) naphthyl group, a 2- (3, 4- dihydro) benzopyranyl group, a 3- ( 3, 4-dihydro) benzopyranyl group, or a 4- (3, 4-dihydro) benzopyranyl group;

r is 1;

is an oxygen atom;

m is 0 or 1; D ¹ is a methyl group;

n is i; ^'

each of R ¹ , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ is a hydrogen atom;

R ² is a hydrogen atom or a methyl group;

the double bond at 2-position of the carbonyl group has E configuration; and

the double bond at 4-position of the carbonyl group has E configuration.

(0024-8) The compound represented by Formula (1-7) wherein X is a phenyl group, a 2-quinolyl group, a 2-thienyl group, a 3, 4-methylenedioxyphenyl group, or a group represented by Formula (II):

wherein a is 1 or 2, and A ¹ is an oxygen atom or -CH ₂ -, and

each of said groups for X may optionally be substituted with the same or different one or more atoms or groups selected from the group consisting of a C1-C4 alkyl group which may optionally be substituted with the same or different one or more halogen atoms, and a halogen atom; r is 0 or 1;

W is -CH2CH2- or -C (CH ₃ ) 2CH2-; n is 1 ;

m is 0 ;

each . of R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ is a hydrogen atom;

the double bond at 2-position of the carbonyl group has E configuration; and

the double bond at 4-position of the carbonyl group- has E configuration.

(0024-9) The compound represented by Formula (1-7) wherein X is a phenyl group, a 2-quinolyl group, a 2-thienyl group, a 3, 4-methylenedioxyphenyl group, or a group represented by Formula (II) :

wherein a is 1 or 2, and A ¹ is an oxygen atom or -CH ₂ -, and

each of said groups for X may optionally be substituted with the same or different one or more atoms or groups selected from the group consisting of a C 1-C4 alkyl group which may optionally be substituted with the same or different one or more halogen atoms, and a halogen atom;

r is 0 or 1;

W is - CH2CH2 - , -C (CH ₃ ) 2CH2 - , - CH2O - , or -SCH ₂ -;

n is i; p is 1;

m is 0 ;

each of R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ is a hydrogen atom;

the double bond at 2-position of the carbonyl group has E configuration; and

the double bond at 4-position of the carbonyl group has E configuration.

(0024-10) The compound represented by Formula (1-7) wherein X is a phenyl group, a pyridyl group, a naphthyl group, a 2-quinolyl group, a 2-thienyl group, a 2-benzofuranyl group, a 3, 4-methylenedioxyphenyl group, or a group represented by Formula (II) :

wherein a is 1 or 2, and A ¹ is an oxygen atom or -CH ₂ -, and

each of said groups for X may optionally be substituted with the same or different one or more atoms or groups selected from the group consisting of a C1-C4 alkyl group which may optionally be substituted with the same or different one or more halogen atoms, a C1-C4 alkoxy group which may optionally be substituted with the same or different one or. more halogen atoms, and a halogen atom; r is 0 or 1;

W is -CH2CH2-, -C (CH ₃ ) 2CH2-, -CH ₂ 0-,. or -SCH ₂ -;

n is 1;

p is 1;

m is 0 ;

R ¹ , R ² , R ³ , and R ⁴ are the same or different to each other and are each independently a C1-C4 alkyl group which may optionally be substituted with the same or different one or more halogen atoms, or a hydrogen atom;

each of R ⁵ , R ⁶ , R ⁷ and R ⁸ is a hydrogen ^■ atom;

the double bond at 2-position of the carbonyl group has E configuration; and

the double bond at 4-position of the carbonyl group has E configuration.

[ 0025]

(0025-1) The compound represented by Formula (I) wherein Y is a tetrahydropyran-2-yl group, a tetrahydropyran-3-yl group or a tetrahydropyran-4-yl group, each of which may optionally be substituted with one atom or group selected from Group D at 3-position of the tetrahydropyran, (i.e., Y is a group represented by Formula (Il-a) wherein Y ¹ is an oxygen atom, and p is 2),

that is, the compound represented by Formula (1-8)

(0025-2) The compound represented by Formula (1-8) wherein m is 0 or 1; and D ¹ is a methyl group.

(0025-3) The compound represented by Formula (1-8) wherein m is 0 or 1; D ¹ is a methyl group; and n is 1.

(0025-4) The compound represented by Formula (1-8) wherein m is 0 or 1;

D ¹ is a methyl group;

n is i;

each of R ¹ , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ is a hydrogen atom; >

R ² is a hydrogen atom or a methyl group;

the double bond at 2-position of the carbonyl group has E. configuration; and

the double bond at 4-position of the carbonyl group has E configuration.

(0025-5) The compound represented, by Formula (1-8) wherein X is a phenyl group, a 3 , 4 -dichlorophenyl group, a 3- trifluoromethylphenyl group, a 3,.5-difluorophenyl group, a 4-methoxyphenyl group, a 2-pyridyl group, a 3-pyridyl group, a 4-pyridyl group, a 1-naphthyl group, a 2-naphthyl group, a 2-guinolyl group, a 3-quinolyl group, a 4-quinolyl group, a 2-furyl group, a 3-furyl group, a 2-thienyl group, a 3- thienyl group, a 2-benzofuranyl group, a 2-benzothienyl group, a 3, 4-methylenedioxyphenyl group, an 1-indanyl group, an 2-indanyl group, a 1- (1, 2, 3, 4-tetrahydro) rtaphthyl group, a 2- (1, 2, 3, 4-tetrahydro) naphthyl group, a 2- (3, 4- dihydro) benzopyranyl group, a 3- (3, 4-dihydro) benzopyranyl group, or a 4- (3, 4-dihydro) benzopyranyl group;

r is 0 or 1;

W is an oxygen atom;

m is 0 or 1;

D ¹ is a methyl group;

n is i;

each of R ¹ , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ is a hydrogen atom;

R ² is a hydrogen atom or a methyl group;

the double bond at 2-position of the carbonyl group has E configuration; and

the double bond at 4-position of the carbonyl group has E configuration.

(0025-6) The compound represented by Formula (1-8) wherein X is a phenyl group, a 3, -dichlorophenyl group, a 3- trifluoromethylphenyl group, a 3 , 5-difluorophenyl group, a 4-methoxyphenyl group, a 2-pyridyl group, a 3-pyridyl group, a 4-pyridyl group, a 1-naphthyl group, a 2-naphthyl group, a 2-guinolyl group, a 3-quinolyl group, a 4-quinolyl group, a 2-furyl group, a 3-furyl group, a 2-thienyl group, a 3- thienyl group, a 2-benzofuranyl group, a 2-benzothienyl group, a 3 , 4 -methylenedioxyphenyl group, an 1-indanyl group, an _. 2-indanyl group, a 1- ( 1 , 2 , 3 , -tetrahydro) naphthyl group, a 2- ( 1 , 2 , 3 , 4-tetrahydro ) naphthyl group, a 2-(3,4- dihydro ) benzopyranyl group, a 3- (3, 4-dihydro) benzopyranyl group, or a 4- ( 3, 4-dihydro) benzopyranyl group;

r is 0 ;

m is 0 or 1;

D ¹ is a methyl group;

n is 1;

each of R ¹ , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ is a hydrogen atom;

R ² is a hydrogen atom or a methyl group;

the double bond at 2-position of the carbonyl group has E configuration; and

the double bond at 4-position of the carbonyl group has E configuration.

(0025-7) ' The compound represented by Formula (1-8) wherein X is a phenyl group, a 3 , 4 -dichlorophenyl group, a 3- trifluoromethylphenyl group, a 3, 5-difluorophenyl group, a 4-methoxyphenyl group, a 2-pyridyl group, a 3-pyridyl group, a 4-pyridyl group, a 1-naphthyl group, a 2-naphthyl group, a 2-quinolyl group, a 3-quinolyl group, a 4-quinolyl group, a 2-furyl group, a 3-furyl group, a 2-thienyl group, a 3- thienyl group, a 2-benzofuranyl group, a 2-benzothienyl group, a 3, 4-methylenedioxyphenyl group, an 1-indanyl group, an 2-indanyl group, a 1- ( 1 , 2 , 3 , 4-tetrahydro) naphthyl group, a 2- (1, 2, 3, 4-tetrahydro) naphthyl group, a 2-(3,4- dihydro ) benzopyranyl group, a 3- (3, 4-dihydro) benzopyranyl group, or a 4- (3, 4-dihydro) benzopyranyl group;

r is 1 ;

W is an oxygen atom;

m is 0 or 1;

D ¹ is a methyl group;.

n is 1 ;

each of R ¹ , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ is a hydrogen atom;

R ² is a hydrogen atom or a methyl group;

the double bond at 2-position of the carbonyl group has. E configuration; and

the double bond at 4-position of the carbonyl group has E configuration.

(0025-8) The compound represented by Formula (1-8) wherein X is a phenyl group, a 2-quinolyl group, a 2-thienyl group, a 3 , 4 -methylenedioxyphenyl group, or a group represented by Formula (II) : wherein a is 1 or 2, and A ¹ is an oxygen atom or -CH ₂ -, and

each of said groups for X may optionally be substituted with the same or different one or more atoms or groups selected from the group consisting of a C1-C4 alkyl group which may optionally be substituted with the same . or different one or more halogen atoms, and a halogen atom; r is 0 or 1;

W is -CH2CH2- or -C (CH ₃ ) 2CH2-;

n is i;

m is 0 ;

each of R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ is a hydrogen atom;

the double bond at 2-position of the carbonyl group has E configuration; and

the double bond at 4-position of the carbonyl group has E configuration.

(0025-9) The compound represented by Formula (1-8) wherein X is a phenyl group, a 2-quinolyl group, a 2-thienyl group, a 3 , 4 -methylenedioxyphenyl group, or a group represented by Formula (II):

wherein a is 1 or 2, and A ¹ is an oxygen atom or -CH ₂ -, and

each of said groups for X may optionally be substituted with the same or different one or more atoms or groups selected from the group consisting of a C 1-C4 alkyl group which may optionally be substituted with the same or different one or more halogen atoms, and a halogen atom; r is 0 or 1;

W is -CH2CH2- , -C (CH ₃ ) 2CH2- , -CH2O - , or - SCH2- ;

n is 1 ;

p is 1

m is 0 ;

each of R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ is a hydrogen atom;

the double bond at 2-position of the carbonyl group has E configuration; and

the double bond at 4-position of the carbonyl group has E configuration.

[ 0026]

(0026-1) The compound represented by Formula (I) wherein Y is a tetrahydropyran-2-yl group which may optionally be substituted with one atom or group selected from Group D at 2-position of the tetrahydropyran (i.e., Y is a group represented by Formula (Il-a) wherein Y ¹ is an oxygen atom, p is 2, m is 0 or 1, D ¹ is attached to 2-position of the tetrahydropyran when m is 1, and the carbon to which R ⁷ and R are atached is attached to 2-position of the tetrahydropyran) ;

that is, the compound represented by Formula (1-9) :

(0026-2) The compound represented by Formula (1-9) wherein m is 0 or 1; and- D ¹ is a methyl group.

(0026-3) The compound _. represented by Formula (1-9) wherein m is 0 or 1; D ¹ is a methyl group; and n is 1.

(0026-4) The compound represented by Formula (1-9) wherein m is 0 or 1;

'D ¹ is a methyl group;

n is 1;

each of R ¹ , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ is a hydrogen atom;

R ² is a hydrogen atom or a methyl group;

the double bond at 2-position of the carbonyl group has E configuration; and

the double bond at 4-position of the carbonyl group has E configuration.

(0026-5) The compound represented by Formula (1-9) wherein X is a phenyl group, a 3 , 4 -dichlorophenyl group, a 3- trifluoromethylphenyl group, a 3 , 5-difluorophenyl group, a 4-methoxyphenyl group, a 2-pyridyl group, a _. 3-pyridyl group, a 4-pyridyl group, a 1-naphthyl group, a 2-naphthyl group, a 2-quinolyl group, a 3-quinolyl group, a 4-quinolyl group, a 2-furyl group, a 3-furyl group, a 2-thienyl group, a 3- thienyl group, a 2-benzofuranyl group, a 2-benzothienyl group, a 3, 4-methylenedioxyphenyl group, an 1-indanyl group, an 2-indanyl group, a 1- ( 1 , 2 , 3 , 4-tetrahydro ) naphthyl group, a 2- (1, 2, 3, 4-tetrahydro) naphthyl group, a 2- (3, 4- dihydro ) benzopyranyl group, a 3- ( 3 , 4-dihydro) benzopyranyl group, or a 4 -( 3 , 4 -dihydro) benzopyranyl group;

r is 0 or 1;

W is an oxygen atom;

m is 0 or 1;

D ¹ is a methyl group;

n is 1;

each of R ¹ , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ is a. hydrogen atom;

R ² is a hydrogen atom or a methyl group;

the double bond at 2-position of the carbonyl group has E configuration; and

the double bond at 4-position of the carbonyl group has E configuration.

(0026-6) The compound represented by Formula (1-9) wherein X is a phenyl group, a 3, 4-dichlorophenyl group, a 3- trifluoromethylphenyl group, a 3 , 5-difluorophenyl group, a 4-methoxyphenyl group, a 2-pyridyl group, a 3-pyridyl group, a 4-pyridyl group, a 1-naphthyl group, a 2-naphthyl group, a 2-guinolyl group, a 3-quinolyl group, a 4-quinolyl group, a 2-furyl group, a 3-furyl group, a 2-thienyl group, a 3- thienyl group, a 2-benzofuranyl group, a 2-benzothienyl group, a 3, 4-methylenedioxyphenyl group, an 1-indanyl group, an 2-indanyl group, a 1- ( 1 , 2 , 3 , 4-tetrahydro) naphthyl group, a 2- ( 1, 2, 3, 4-tetrahydro) naphthyl group, a 2-(3,4- dihydro ) benzopyranyl group, a 3- (3, 4-dihydro) benzopyranyl group, or a 4- (3, -dihydro) benzopyranyl group;

r is 0; '

m is 0 or 1;

D ¹ is a methyl group;

• ^■ n is i;

each of R ¹ , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ is a hydrogen atom;

R ² is a hydrogen atom or a methyl group;

the double bond at 2-position of the carbonyl group has E configuration; and

the double bond at 4-position of the carbonyl group has E configuration.

(0026-7) The compound represented by Formula (1-9) wherein X is a phenyl group, a 3, -dichlorophenyl group, a 3- trifluoromethylphenyl group, a 3 , 5-difluorophenyl group, a 4-methoxyphenyl group, a 2-pyridyl group, a 3-pyridyl group, a 4-pyridyl group, a 1-naphthyl group, a 2-naphthyl group, a 2-quinolyl group, a 3-quinolyl group, a 4-quinolyl group, a 2-furyl group, a 3-furyl group, a 2-thienyl group, a 3- thienyl group, a 2-benzofuranyl group, a 2-benzothienyl group, a 3 , 4-methylenedioxyphenyl group, an 1-indanyl group, an 2-indanyl group, a 1- ( 1 , 2 , 3 , 4 -tetrahydro) naphthyl group, a 2- ( 1 , 2 , 3., 4-tetrahydro) naphthyl group, a 2- (3, 4- dihydro) enzopyranyl group, a 3- (3, 4-dihydro) benzopyranyl group, or a 4- (3, 4-dihydro) benzopyranyl group;

r is 1;

W is an oxygen atom;

m is 0 or 1;

D ¹ is a methyl group;

n is 1 ;

each of R ¹ , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ is a hydrogen atom;

R ² is a hydrogen atom or a methyl group;

the double bond at 2-position of the carbonyl group has E configuration; and

the double bond at 4-position of the carbonyl group has E configuration.

(0026-8) The compound represented by Formula (1-9) wherein X is a phenyl group, a 2-quinolyl group, a 2-thienyl group, a 3, -methylenedioxyphenyl group, or a group represented by Formula (II):

wherein a is 1 or 2, and A ¹ is an oxygen atom or -CH ₂ -, and

each of said groups for X may optionally be substituted with the same or different one or more atoms or groups selected from the group consisting of a Ci-C alkyl group which may optionally be substituted with the same or different one or more halogen atoms, and a halogen atom; r is 0 or 1;

W is -CH ₂ CH ₂ - or -C (CH ₃ ) ₂ CH ₂ - ;

n i s 1 ;

m i s 0 ;

each of R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ is a hydrogen atom;

the double bond at 2-position of the carbonyl group has E configuration; and

the double bond at 4-position of the carbonyl group has E configuration.

(0026-9) The compound represented by Formula (1-9) wherein X is a phenyl group, a 2-quinolyl group, a 2-thienyl group, a 3, 4-methylenedioxyphenyl group, or a group represented by Formula (II) :

wherein a is 1 or 2, and A ¹ is an oxygen atom or -CH ₂ -, and

each of said groups for X may optionally be substituted with the same or different one or more atoms or groups selected from the group consisting of a C 1-C4 alkyl group which may optionally be substituted with the same or different one or more halogen atoms, and a halogen atom; r is 0 or 1;

W is -CH2CH2 - , -C (CH ₃ ) 2CH2 - , - CH2O - , or - S CH2 - ;

is i;

p is 1;

m is 0 ;

each of R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ is a hydrogen atom;

the double bond at 2-position of the carbonyl group has E configuration; and

the double bond at 4-position of the carbonyl group has E configuration.

t 0027]

(0027-1) The compound represented by Formula (I) wherein Y is a tetrahydropyran-3-yl group which may optionally be substituted with one atom or group selected from Group D at 3-position of the tetrahydropyran (i.e., Y is a group represented by Formula (Il-a) wherein Y ¹ is an oxygen atom, p is 2, m is 0 or 1, D ¹ is attached to 3-position of the tetrahydropyran when m is 1, and the carbon to which R ⁷ and R ⁸ are atached is attached to 3-pos ^' ition of the tetrahydropyran) ;

that is, the compound represented by Formula (1-10):

(0027-2) The compound . represented by Formula (1-10) wherein m is 0 or 1; and D ¹ is a methyl group.

(0027-3) The compound represented by Formula (1-10) wherein m is 0 or 1; D ¹ is a methyl group; and n is 1.

(0027-4) The compound represented by Formula (1-10) wherein

m is 0 or 1;

D ¹ is a methyl group;

n is 1;

each of R ¹ , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ is a hydrogen atom;

R ² is a hydrogen atom or a methyl group;

the double bond at 2-position of the carbonyl group has E configuration; and the double bond at 4-position of the carbonyl group has E configuration.

(0027-5) The compound represented by Formula (1-10) wherein

X is a phenyl group, a 3, 4 -dichlorophenyl group, a 3- trifluoromethylphenyl group, a 3 , 5-difluorophenyl group, a 4-methoxyphenyl group, a 2-pyridyl group, a 3-pyridyl group, a 4-pyridyl group, a 1-naphthyl group, a 2-naphthyl group, a 2-quinolyl group, a 3-quinolyl group, a 4-quinolyl group, a 2-furyl group, a 3-furyl group, a 2-thienyl group, a 3- thienyl group, a 2-benzofuranyl group, a 2-benzothienyl group, a 3, 4-methylenedioxyphenyl group, an 1-indanyl group, an 2-indanyl group, a 1- (1, 2, 3, 4-tetrahydro) naphthyl group, a 2- (1, 2, 3, 4-tetrahydro) naphthyl group, a 2- (3, 4- dihydro) benzopyranyl group, a 3- ( 3, 4-dihydro) benzopyranyl group, or a 4- (3, 4-dihydro) benzopyranyl group;

r is 0 or 1;

W is an oxygen atom;

m is 0 or 1;

D ¹ is a methyl group;

n is 1;

each of R ¹ , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ is a hydrogen atom;

R ² is a hydrogen atom or a methyl group;

the double bond at 2-position of the carbonyl group has E configuration; and

the double bond at 4 -position of the carbonyl group has E configuration.

(0027-6) The compound represented by Formula (1-10) wherein

X is a phenyl group, a 3 , 4 -dichlorophenyl group, a 3- trifluoromethylphenyl group, a 3 , 5-difluorophenyl group, a 4-methoxyphenyl group, a 2-pyridyl group, a 3-pyridyl group, a 4-pyridyl group, a 1-naphthyl group, a 2-naphthyl group, a 2-quinolyl group, a 3-quinolyl group, a 4-quinolyl group, a 2-furyl group, a 3-furyl group, a 2-thienyl group, a 3- thienyl group, a 2-benzofuranyl group, a 2-benzothienyl group, a 3, 4-methylenedioxyphenyl group, an 1-indanyl group, an 2-indanyl group, a 1- ( 1 , 2 , 3 , 4-tetrahydro ) naphthyl group, a 2- (1, 2, 3, 4-tetrahydro) naphthyl group, a 2- (3, 4- dihydro) benzopyranyl group, a 3- (3, 4-dihydro) benzopyranyl group, or a 4- (3, 4^dihydro) benzopyranyl group;

r is 0 ;

m is 0 or 1;

D ¹ is a methyl group;

n is 1;

each of R ¹ , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ is a hydrogen atom;

R ² is a hydrogen atom or a methyl group;

the double bond at 2-position of the carbonyl group has E configuration; and

the double bond at 4-position of the carbonyl group has E configuration.

(0027-7) The compound represented by Formula (1-10) wherein

X is a phenyl group, a 3, 4-dichlorophenyl group, a 3- trifluoromethylphenyl group, a 3 , 5-difluorophenyl group, a 4-methoxyphenyl group, a 2-pyridyl group, a 3-pyridyl group, a 4-pyridyl group, a 1-naphthyl group, a 2-naphthyl group, a 2-quinolyl group, a 3-quinolyl group, a 4-quinolyl group, a 2-furyl group, a 3-furyl group, a 2-thienyl group, a 3- thienyl group, a 2-benzofuranyl group, a 2-benzothienyl group, a 3, 4-methylenedioxyphenyl group, an 1-indanyl group, an 2-indanyl group, a 1- (1, 2, 3, 4-tetrahydro) naphthyl group, a 2- (1, 2, 3, 4-tetrahydro) naphthyl group, a 2-(3,4- dihydro ) benzopyranyl group, a 3- (3, 4-dihydro) benzopyranyl group, or a 4- (3, 4-dihydro) benzopyranyl group; .

r is .1 ;

W is an oxygen atom;

m is 0 or 1;

D ¹ is a methyl group;

n is 1;

each of R ¹ , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ is a hydrogen atom;

R ² is a hydrogen atom or a methyl group; the double bond at 2-position of the carbonyl group has E configuration; and

the double bond at 4-position of the carbonyl group has E configuration.

(0027-8) The compound represented by Formula (1-10) wherein

X is a phenyl group, a 2-quinolyl group, a 2-thienyl group, a 3, 4-methylenedioxyphenyl group, or a group represented by Formula (II):

wherein a is 1 or 2, and A ¹ is an oxygen atom or - CH2 - , and

each of said groups for X may optionally be substituted with the same or different one or more atoms or groups selected from the group consisting of a C 1-C4 alkyl group which may optionally be substituted with the same or different one or more halogen atoms, and a halogen atom; r is 0 or 1;

W is -CH2CH2 - or -C (CH ₃ ) 2CH2 - ;

n is 1 ;

m is 0 ;

each of R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ is a hydrogen atom; the double bond at 2-position of the carbonyl group has E configuration; and

the double bond at 4-position of the carbonyl group has E configuration.

(0027-9) The compound represented by Formula (1-10) wherein

X is a phenyl group, a 2-quinolyl group, a 2-thienyl group, a 3 , -methylenedioxyphenyl group, or a group represented by Formula (II) :

wherein a is 1 or 2, and A ¹ is an oxygen atom or -CH ₂ -, and

each of said groups for X may optionally be substituted with the same or different one or more atoms or groups selected from the group consisting of a Ci-C ₄ alkyl group which may optionally be substituted with the same or different one or more halogen atoms, and a halogen atom; r is 0 or 1;

W is -CH2CH2 - , -C (CH ₃ ) 2CH2- , - CH2O - , or -SCH ₂ -;

n is 1;

p is 1;

m is 0;

each of R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ is a hydrogen atom;

the double bond at 2-position of the carbonyl group has E configuration; and

the double bond at 4-position of the carbonyl group has E configuration.

[ 0028]

(0028-1) The compound represented by Formula (I) wherein Y is a tetrahydropyran-4-yl group which may optionally be substituted with one atom or group selected from Group D at 4-position of the tetrahydropyran (i.e., Y is a group represented by Formula (Il-a) wherein Y ¹ is an oxygen atom, p is 2, m is 0 or 1, D ¹ is attached to 4 -position ^' of the tetrahydropyran when m is 1, and the carbon to which R ⁷ and R ⁸ are atached is attached to 4-position of the tetrahydropyran) ;

that is, the compound represented by Formula (1-11)

(0028-2) The compound represented by Formula (1-11) wherein m' is 0 or 1; and D ¹ is a methyl group.

(0028-3) The compound represented by Formula (1-11) wherein m is 0 or 1; D ¹ is a methyl group; and n is 1.

(0028-4) The compound represented by Formula (1-11) wherein

m is 0 or 1;

D ¹ is a methyl group;

n is 1;

each of R ¹ , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ is a hydrogen atom;

R ² is a hydrogen atom or a methyl group;

the double bond at 2-position of the carbonyl group has E configuration; and

the double bond at 4-position of the carbonyl group has E configuration. · '

(0028-5) The compound represented by Formula (1-11) wherein

X is a phenyl group, a 3, 4-dichlorophenyl group, a 3- trifluoromethylphenyl group, a 3 , 5-difluorophenyl group, a 4-methoxyphenyl group, a 2-pyridyl group, a 3-pyridyl group, a 4-pyridyl group, a 1-naphthyl group, a 2-naphthyl group, a 2-quinolyl group, a 3-quinolyl group, a 4-quinolyl group, a 2-furyl group, a 3-furyl group, a 2-thienyl group, . a 3- thienyl group, a 2-benzofuranyl group, a 2-benzothienyl group, a 3, 4-methylenedioxyphenyl group, an 1-indanyl group, an 2-indanyl group, a 1- ( 1 , 2 , 3 , 4-tetrahydro ) naphthyl group, a 2- ( 1 , 2 , 3, 4-tetrahydro) naphthyl group, a 2- (3, 4- dihydro) benzopyranyl group, a 3- (3, 4-dihydro) benzopyranyl group, or a 4- (3, 4-dihydro) benzopyranyl group; r is 0 or 1;

W is an oxygen atom;

m is 0 or 1;

D ¹ is a methyl group;

n is 1;

each of R ¹ , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ is a hydrogen atom;

R ² is a hydrogen atom or a methyl group;

the double bond at 2-position of the ^' carbonyl group has E configuration; and

the double bond at 4-position of the carbonyl group has E configuration.

(0028-6) The compound represented by Formula (1-11) wherein

X is a phenyl group, a 3, 4-dichlorophenyl group, a 3- trifluoromethylphenyl group, a 3 , 5-difluorophenyl group, a 4-methoxyphenyl group, a 2-pyridyl group, a 3-pyridyl group, a 4-pyridyl group, a 1-naphthyl group, a 2-naphthyl group, a 2-quinolyl group, a 3-quinolyl group, a 4-quinolyl group, a 2-furyl group, a 3-furyl group, a 2-thienyl group, a 3- thienyl group, a 2-benzofuranyl group, a 2-benzothienyl group, a 3 , 4 -methylenedioxyphenyl group, an 1-indanyl group, an 2-indanyl group, a 1- ( 1 , 2 , 3 , 4-tetrahydro ) naphthyl group, a 2- (1, 2, 3, 4-tetrahydro) naphthyl group, a 2-(3,4- dihydro ) benzopyranyl group, a 3- (3, 4-dihydro) benzopyranyl group, or a 4- (3, 4-dihydro) benzopyranyl group;

r is 0 ;

m is 0 or 1;

D ¹ is a methyl group;

n is 1 ;

each of R ¹ , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ is a hydrogen atom;

R ² is a hydrogen atom or a methyl group;

the double bond at 2-position of the carbonyl group has E configuration; and

the double bond at 4-position of the carbonyl group has E configuration.

(0028-7) The compound represented by Formula (1-11) wherein

X is a phenyl group, a 3, 4-dichlorophenyl group, a 3- trifluoromethylphenyl group, a 3 , 5-difluorophenyl group, a 4-methoxyphenyl group, a 2-pyridyl group, a 3-pyridyl group, a 4-pyridyl group, a 1-naphthyl group, a 2-naphthyl group, a 2-quinolyl group, a 3-quinolyl group, a 4-quinolyl group, a 2-furyl group, a 3-furyl group, a 2-thienyl group, a 3- thienyl group, a 2-benzofuranyl group, a 2-benzothienyl group, a 3, 4-methylenedioxyphenyl group, an 1-indanyl group, an 2-indanyl group, a 1- ( 1 , 2 , 3 , 4-tetrahydro) naphthyl group, a 2- (Ί, 2, 3, 4-tetrahydro) naphthyl group, a 2- (3, - dihydro ) benzopyranyl group, a 3- ( 3 , 4-dihydro ) benzopyranyl group, or a 4- (3, 4-dihydro) benzopyranyl group;

r is 1 ;

W is an oxygen atom;

m is 0 or 1;

D ¹ is a methyl group;

n is i;

each of R ¹ , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ is a hydrogen atom;

R ² is a hydrogen atom or a methyl group;

the double bond at 2-position of the carbonyl group has E configuration; and

the double bond at 4-position of the carbonyl group has E configuration.

(0028-8) The compound represented by Formula (1-11) wherein

X is a phenyl group, a 2-quinolyl group, a 2-thienyl group, a 3 , 4 -methylenedioxyphenyl group, or a group represented by Formula (II):

wherein a is 1 or 2, and A is an oxygen atom or -CH ₂ -, and

each of said groups for X may optionally be substituted with the same or different one or more atoms or groups selected from the group consisting of a C ₁ -C4 alkyl group which may optionally be substituted with the same or different one or more halogen atoms, and a halogen atom; r is 0 or 1;

W is -CH2CH2- or -C (CH ₃ ) 2CH ₂ -;

n is i;

m is 0;

each of R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ is a hydrogen atom;

the double bond at 2-position of the carbonyl group has E configuration; and

the double bond at 4-position of the carbonyl group has E configuration.

(0028-9) The compound represented by Formula (1-11) wherein

X is a phenyl group, a 2-quinolyl group, a 2-thienyl group, a . 3 ,4 -methylenedioxyphenyl group, or a group represented by Formula (II):

wherein a is 1 or 2, and A ¹ is. an oxygen atom or -CH ₂ -, and

each of said groups for X may optionally be substituted with the same or different one or more atoms or groups selected from the group consisting of a C 1-C4 alkyl group which may optionally be substituted with the same or different one or more halogen atoms, and a halogen atom; r is 0 or 1;

W is -CH2CH2 - , -C (CH ₃ ) 2CH2 - , - CH2O - , or -SCH ₂ -;

n is 1;

p is 1;

m is 0 ;

each of R ¹ , R ² , R ³ ,. R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ is a hydrogen atom;

the double bond at 2-position of the carbonyl group has E configuration; and

the double bond at 4-position of the carbonyl group has E configuration.

[ 0029]

(0029-1) The compound represented by Formula (I) wherein Y is a group represented by Formula (Il-b), m is 0 or 1, and q is 0 or 1;

that is, the compound represented by Formula (1-12):

(0029-2) The compound represented by Formula (1-12) wherein m is 0 or 1; q is 0 or 1; and D ¹ is a methyl group. (0029-3) The compound represented by Formula (1-12) wherein m is 0 or 1; q is 0 or 1; D ¹ is a methyl group; and n is i.

(0029-4) The compound represented by Formula (1-12) wherein

m is 0 or 1;

q is 0 or 1;

D ¹ is a methyl group;

n is i;

each of R ¹ , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ is a hydrogen atom;

R ² is a hydrogen atom or a methyl group; .

the double bond at 2-position of the carbonyl group has E configuration; and

the double bond at 4-position of the.. carbonyl group has E configuration.

(0029-5) The compound represented by Formula (1-12) wherein

X is a phenyl group, a 3, 4-dichlorophenyl group, a 3- trifluoromethylphenyl group, a 3 , 5-difluorophenyl group, a 4-methoxyphenyl group, a 2-pyridyl group, a 3-pyridyl group, a 4-pyridyl group, a 1-naphthyl group, a 2-naphthyl group, a 2-quinolyl group, a 3-quinolyl group, a 4-quinolyl group, a 2-furyl group, a 3-furyl group, a 2-thienyl group, a 3- thienyl group, a 2-benzof ranyl group, a 2-benzothienyl group, a 3, 4-methylenedioxyphenyl group, an 1-indanyl group, an 2-indanyl group, a 1- ( 1 , 2 , 3, 4-tetrahydro) naphthyl group, a 2- (1, 2, 3, 4-tetrahydro) naphthyl group, a 2-(3,4- dihydro ) benzopyranyl group, a 3- (3, 4-dihydro) benzopyranyl group, or a 4 -( 3 , 4-dihydro ) benzopyranyl group;

r is 0 or 1 ;

W is an oxygen atom;

m is 0 or 1;

q is 0 or 1;

D ¹ is a methyl group;

n is i;

each of R ¹ , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ is a hydrogen atom;

R ² is a hydrogen atom or a methyl group;

the double bond at 2-position of the carbonyl group has E configuration; and

the double bond at 4-position of the carbonyl group has E configuration.

(0029-6) The compound represented by Formula (1-12) wherein

X is a phenyl group, a 3, 4-dichlorophenyl group, a 3- trifluoromethylphenyl group, a 3 , 5-difluorophenyl group, a 4-methoxyphenyl group, a 2-pyridyl group, a 3-pyridyl group, a 4-pyridyl group, a 1-naphthyl group, a 2-naphthyl group, a 2-quinolyl group, a 3-quinolyl group, a 4-quinolyl group, a 2-furyl group, a 3-furyl group, a 2-thienyl group, a 3- thienyl group, a 2-benzofuranyl group, a 2-benzothienyl group, a 3 , 4-methylenedioxyphenyl group, an 1-indanyl group, an 2-indanyl group, a 1- (1, 2, 3, 4-tetrahydro) naphthyl group, a 2- (1, 2, 3, 4-tetrahydro) naphthyl group, a 2-(3,4- dihydro) benzopyranyl group, a 3- (3, 4-dihydro) benzopyranyl group, or a 4- (3, 4-dihydro) benzopyranyl group;

r is 0 ;

m is 0 or 1 ;

q is 0 or 1;

D ¹ is a methyl group;

n is i;

each of R ¹ , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ is a hydrogen atom;

R ² is a hydrogen atom or a methyl group;

the double bond at 2-position of the carbonyl group has E configuration; and

the double bond at 4-position of the carbonyl group has E configuration.

(0029-7) The compound represented by Formula (1-12) wherein

X is a phenyl group, a 3, 4-dichlorophenyl group, a 3- trifluoromethylphenyl group, a 3, 5-difluorophenyl group, a 4-methoxyphenyl group, a 2-pyridyl group, a 3-pyridyl group, a 4-pyridyl group, a 1-naphthyl group, a 2-naphthyl group, a 2-quinolyl group, a 3-quinolyl group, a 4-quinolyl group, a 2-furyl group, a 3-furyl group, a 2-thienyl group, a 3- thienyl group, a 2-benzofuranyl group, a 2-benzothienyl group, a 3 , -methylenedioxyphenyl group, an 1-indanyl group, an 2-indanyl group, a 1- (1, 2, 3, 4-tetrahydro) naphthyl group, a 2- (1, 2, 3, -tetrahydro) naphthyl group, a 2-(3,4- dihydro) benzopyranyl group, a 3- (3, 4-dihydro) benzopyranyl group, or a 4- (3, 4-dihydro) benzopyranyl group;

r is 1 ;

W is an oxygen atom;

m is 0 or 1;

q is 0 or 1;

D ¹ is a methyl group;

n is i;

each of R ¹ , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ is a hydrogen atom;

R ² is a hydrogen atom or a methyl group;

the double bond at 2-position of the carbonyl group has E configuration; and

the double bond at 4-position of the carbonyl group has E configuration.

(0029-8) The compound represented by Formula (1-12) wherein

X is a phenyl group, a 2-quinolyl group, a 2-thienyl group, a 3 , -methylenedioxyphenyl group, or a group represented by Formula (II) :

wherein a is 1 or 2, and A is an oxygen atom or -CH ₂ -, and

each of said groups for X may optionally be substituted with the same or different one or more atoms or groups selected from the group consisting of a Ci-C ₄ alkyl group which may optionally be substituted with the same or different one or more halogen atoms, and a halogen atom; r is 0 or 1;

W is -CH2CH2- or -C (CH ₃ ) 2CH2-;

n is 1 ;

m is 0 ;

each of R ¹ , R ² , R ³ , R ⁴ , -R ⁵ , R ⁶ , R ⁷ and R ⁸ is a hydrogen atom;

the double bond at 2-position of the carbonyl group has E configuration; and

the double bond at 4-position of the carbonyl group has E configuration.

(0029-9) The compound represented by Formula (1-12) wherein

X is a phenyl group, a 2-quinolyl group, a 2-thienyl group, a 3, 4-methylenedioxyphenyl group, or a group represented by Formula (II) :

wherein a is 1 or 2, and A ¹ is an oxygen atom or -CH ₂ -, and

each of said groups for X may optionally be substituted with the same or different one or more atoms or groups selected from the group consisting of a C 1-C4 alkyl group which may optionally be substituted with the same or different one or more halogen atoms, and a halogen atom; r is 0 or 1;

W is -CH2CH2- , -C (CH ₃ ) 2CH2 - , -CH2O - , or -SCH ₂ -;

. n is i;

p is 1;

m is 0 ;

each of R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ is a hydrogen atom;

the double bond at 2-position of the carbonyl group has E configuration; and

the double bond at 4-position of the carbonyl group has E configuration.

[ 0030]

(0030-1) The compound represented by Formula (I) wherein Y is a [ 1 , 3] dioxolan-4 -yl group which may optionally be substituted with one atom or group selected from Group D at 4-position of the [ 1 , 3] dioxolane (i.e., Y is a group represented by Formula (Il-b) wherein q is 0, and m is 0 or l ) ;

that is, the compound represented by Formula (1-13) :

(0030-2) The compound represented by Formula (1-13) wherein m is 0 or 1; and D ¹ is a methyl group.

(0030-3) The compound represented by Formula (1-13) wherein m is 0 or 1; D ¹ is a methyl group; and n is 1.

(0030-4) The compound represented by Formula (1-13) wherein

m is 0 or 1;

D ¹ is a methyl group;

n is i;

each of R ¹ , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ is a hydrogen atom;

R ² is a hydrogen atom or a methyl group;

the double bond at 2-position of the carbonyl group has E configuration; and

the double bond at 4-position of the carbonyl group has E configuration. (0030-5) The compound represented by Formula (1-13) wherein

X is a phenyl group, a 3 , 4 -dichlorophenyl group, a 3- trifluoromethylphenyl group, a 3 , 5-difluorophenyl group, a 4-methoxyphenyl group, a 2-pyridyl group, a 3-pyridyl group, a 4-pyridyl group, a 1-naphthyl group, a 2-naphthyl group, a 2-quinolyl group, a 3-quinolyl group, a 4-quinolyl group, a 2-furyl group, a 3-furyl group, a 2-thienyl group, a 3- thienyl group, a 2-benzofuranyl group, a 2—benzothienyl group, a 3, 4-methylenedioxyphenyl group, an 1-indanyl group, an 2-indanyl group, a 1- (1, 2, 3, 4-tetrahydro) naphthyl group, a 2- (1, 2, 3, 4-tetrahydro) naphthyl group, a 2-(3,4- dihydro) benzopyranyl group, a 3- (3, 4-dihydro) benzopyranyl group, or a 4- (3, 4-dihydro) benzopyranyl group;

r is 0 or 1;

W is an oxygen atom;

m is 0 or 1;

D ¹ is a methyl group;

n is i;

each of R ¹ , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ is a hydrogen atom;

R ² is a hydrogen atom or a methyl group;

the double bond at 2-position of the carbonyl group has E configuration; and

the double bond at 4-position of the carbonyl group has E configuration.

(0030-6) The compound represented by Formula (1-13) wherein

X is a phenyl group, a 3, 4-dichlorophenyl group, a 3- trifluoromethylphenyl group, a 3 , 5-difluorophenyl group, a 4-methoxyphenyl group, a 2-pyridyl group, a. 3-pyridyl group, a 4-pyridyl group, a 1-naphthyl group, a 2-naphthyl group, a 2-quinolyl group, a 3-quinolyl group, a 4-quinolyl group, a 2-furyl group, a 3-furyl group, a 2-thienyl group, a 3- thienyl group, a 2-benzofuranyl group, a 2-benzothienyl group, a 3 , 4 -methylenedioxyphenyl group, an 1-indanyl group, an 2-indanyl group, a 1- (1, 2, 3, 4-tetrahydro) naphthyl group, a 2- (1, 2, 3, 4-tetrahydro) naphthyl group, a 2- (3, 4- dihydro) benzopyranyl group, ^' a 3- (3, 4-dihydro) benzopyranyl group, or a 4- (3, 4-dihydro) benzopyranyl group;

r is 0;

m is 0 or 1;

D ¹ is a methyl group;

n is i;

each of R ¹ , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ is a hydrogen atom;

R ² is a hydrogen atom or a methyl group;

the double bond at 2-position of the carbonyl group has E configuration; and

the double bond at 4-position of the carbonyl group has E configuration.

(0030-7) The compound represented by Formula (1-13) wherein

X is a phenyl group, a 3, 4 -dichlorophenyl group, a 3- trifluoromethylphenyl group, a 3 , 5-difluorophenyl group, a 4-methoxyphenyl group, a 2-pyridyl group, a 3-pyridyl group, a 4-pyridyl group, a 1-naphthyl group, a 2-naphthyl group, a 2-quinolyl group, a 3-quinolyl group, a 4-quinolyl group, a 2-furyl group, a 3-furyl group, a 2-thienyl group, a 3- thienyl group, a 2-benzofuranyl group, a 2-benzothienyl group, a 3, 4-methylenedioxyphenyl group, an 1-indanyl group, an 2-indanyl group, a 1- ( 1 , 2 , 3, 4-tetrahydro ) naphthyl group, a 2- (1, 2, 3, 4-tetrahydro) naphthyl group, a 2- (3, 4- dihydro ) benzopyranyl group, a 3- (3, 4-dihydro) benzopyranyl group, or a 4- ( 3, 4-dihydro) benzopyranyl group;

r is 1 ;

W is an oxygen atom;

m is 0 or 1;

D ¹ is a methyl group;

n is 1;

each of R ¹ , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ is a hydrogen atom;

R ² is a hydrogen atom or a methyl group;

the double bond at 2-position of the carbonyl group has E configuration; and the double bond at 4-position of the carbonyl group has E configuration.

(0030-8) The compound represented by Formula (1-13) wherein

X is a phenyl group, a 2-quinolyl group, a 2-thienyl group, a 3 , 4 -methylenedioxyphenyl group, or a group represented by Formula (II) :

wherein a is 1 or 2, and A is an oxygen atom or -C¾-, and

each of said groups for X may optionally be substituted with the same or different one or more atoms or groups selected from the group consisting of a C1-C4 alkyl group which may optionally be substituted with the same or different one or more halogen atoms, and a halogen atom; r is 0 or 1;

W is -CH2CH2- or -C (CH ₃ ) 2CH2-;

n is 1 ;

m is 0 ;

each of R ¹ , R ² , R ³ , R R ⁵ , R ⁶ , R ⁷ and R ⁸ is a hydrogen atom;

the double bond at 2-position of the carbonyl group has E configuration; and the double bond at .4-position of the carbonyl. group has E configuration.

(0030-9) The compound represented by Formula (1-13) wherein

X is a phenyl group, a 2-quinolyl group, a 2-thienyl group, a 3 , 4 -methylenedioxyphenyl group, or a group represented by Formula (II) :

wherein a is 1 or 2, and A ¹ is an oxygen atom or -CH2- , and

each of said groups for X . may optionally be substituted with the same or different one or more atoms or groups selected from the group consisting of a C 1-C4 alkyl group which may optionally be substituted with the same or different one or more halogen atoms, and a halogen atom; r is 0 or 1;

W is - CH2CH2 - , -C (CH ₃ ) 2CH2 - , -CH2O - , or -SCH ₂ -;

n is _. 1;

p is 1;

m is 0 ;

each of R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ is a hydrogen atom;

the double bond at 2-position of the carbonyl group has E configuration; and

the double bond at 4-position of the carbonyl group has E configuration.

[ 0031]

(0031-1) The compound represented by Formula (I) wherein Y is a [ 1,3] dioxan-5-yl group which may optionally be substituted with one atom or group selected from Group D at 5-position of the [ 1,3] dioxane (i.e., Y is a group represented by Formula (Il-b) wherein q is 1, and m is 0 or 1);

that is, the compound represented by Formula (1-14)

(0031-2) The compound represented by Formula (1-14) wherein m is 0 or 1; and.D ¹ is a methyl group.

(0031-3) The compound represented by Formula (1-14) wherein m is 0 or 1; D ¹ is a methyl group; and n is 1.

(0031-4) The compound represented by Formula (1-14) wherein

m is 0 or 1 ;

D ¹ is a methyl group;

n is i;

each of R ¹ , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ is a hydrogen atom;

R ² is a hydrogen atom or a methyl group;

the double bond at 2-position of the carbonyl group has E configuration; and

the double bond at 4-position of the carbonyl group has E configuration.

(0031-5) The compound represented by Formula (1-14) wherein

X is a phenyl group, a 3, 4-dichlorophenyl group, a 3- trifluoromethylphenyl group, a 3 , 5-difluorophenyl group, a 4-methoxyphenyl group, a 2-pyridyl group, a 3-pyridyl group a 4-pyridyl group, a 1-naphthyl group, a 2-naphthyl group, a 2-quinolyl group, a 3-quinolyl group, a 4-quinolyl group, a 2-furyl group, a 3-furyl group, a 2-thienyl group, a 3- thienyl group, a 2-benzofuranyl group, a 2-benzothienyl group, a 3, 4-methylenedioxyphenyl group, an 1—indanyl group an 2-indanyl group, a 1- ( 1 , 2 , 3 , 4-tetrahydro ) naphthyl group, a 2- (1, 2, 3, 4-tetrahydro) naphthyl group, a 2- (3, - dihydro ) benzopyranyl group, a 3- (3, 4-dihydro) benzopyranyl group, or a 4- (3, 4-dihydro) benzopyranyl group;

r is 0 or 1;

W is an oxygen atom;

m is 0 or 1;

D ¹ is a methyl group;

n is i; ^" each of R ¹ , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ is a hydrogen atom;

R ² is a hydrogen atom or a methyl group;

the double bond at 2-position of the carbonyl group has E configuration; and

the double bond at 4-position of the carbonyl group has E configuration.

(0031-6) The compound represented by Formula (1-14) wherein

X is a phenyl group, a 3 , 4-dichlorophenyl group, a 3- trifluoromethylphenyl group, a 3 , 5-difluorophenyl group, a 4-methoxyphenyl group, a 2-pyridyl group, a 3-pyridyl group, a 4-pyridyl group, a 1-naphthyl group, a 2-naphthyl group, a 2-quinolyl group, a 3-quinolyl group, a 4-quinolyl group, a 2-furyl group, a 3-furyl group, a 2-thienyl group, a 3- thienyl group, a 2-benzofuranyl group, a 2-benzothienyl group, a 3 , 4 -methylenedioxyphenyl group, an 1-indanyl group, an 2-indanyl group, a 1- ( 1 , 2 , 3 , 4-tetrahydro) naphthyl group, a 2- (1, 2, 3, 4-tetrahydro) naphthyl group, a 2- (3, 4-' dihydro) benzopyranyl group, a 3- (3, 4-dihydro) benzopyranyl group, or a 4- (3, 4-dihydro) benzopyranyl group;

r is 0; ·

m is 0 or 1;

D ¹ is a methyl group;

n is 1; each of R ¹ , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ is a hydrogen atom;

R ² is a hydrogen atom or a methyl group;

the double bond at 2-position of the carbonyl group has E configuration; and

the double bond at 4-position of the carbonyl group has E configuration.

(0031-7) The compound represented by Formula (1-14) wherein

X is a . phenyl group, a 3, 4-dichlorophenyl group, a 3- trifluoromethylphenyl group, a 3 , 5-difluorophenyl group, a 4-methoxyphenyl group, a 2-pyridyl group, a 3-pyridyl group, a 4-pyridyl group, a 1-naphthyl group, a 2-naphthyl group, a 2-quinolyl group, a 3-quinolyl group, a 4-quinolyl group, a 2-furyl group, a 3-furyl group, a 2-thienyl group, a 3- thienyl group, a 2-benzofuranyl group, a 2-benzothienyl group, a 3 , 4-methylenedioxyphenyl group, an 1-indanyl group, an 2-indanyl group, a 1- ( 1 , 2 , 3 , 4 -tetrahydro ) naphthyl group, a 2- ( 1 , 2 , 3 , 4-tetrahydro ) naphthyl group, a 2- (3, 4- dihydro) benzopyranyl group, a 3- (3, 4-dihydro) benzopyranyl group, or a 4- (3, 4-dihydro) benzopyranyl group;

r is 1;

is an oxygen atom;

m is 0 or 1;

D ¹ is a methyl group; n is 1 ;

each of R ¹ , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ is a hydrogen atom;

R ² is a hydrogen atom or a methyl group;

the double bond at 2-position of the carbonyl group has E configuration; and

the double bond at 4-position of the carbonyl group has E configuration.

(0031-8) The compound represented by Formula (1-14) wherein

X is a phenyl group, a 2-quinolyl group, a 2-thienyl group, a 3, 4-methylenedioxyphenyl group, or a group represented by Formula (II) :

wherein a is 1 or 2, and A is an oxygen atom or -CH ₂ -, and

each of said groups for X may optionally substituted with the same or different one or more atoms or groups selected from the group consisting of a Ci-C alkyl group which may optionally be substituted with the same or different one or more halogen atoms, and a halogen atom; r is 0 or 1;

W is -CH ₂ CH ₂ - or -C (CH ₃ ) ₂ CH ₂ -; n is 1 ;

m is 0;

each of R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ is a hydrogen atom;

the double bond at 2-position of the carbonyl group has E configuration; and

the double bond at 4-position of the carbonyl group has E configuration.

(0031-9) The compound represented by Formula (1-14) wherein

X is a phenyl group, a 2-quinolyl group, a 2-thienyl group, a 3, 4-methylenedioxyphenyl group, or a group represented by Formula (II):

wherein a is 1 or 2, and A is an oxygen atom or -CH ₂ -, and

each of said groups for X may optionally be substituted with the same or different one or more atoms or groups selected from the group consisting of a C i -C ₄ alkyl group which may optionally be substituted with the same or different one or more halogen atoms, and a halogen atom; . r is 0 or 1 ;

W is -CH2CH2 - , -C (CH ₃ ) 2CH2- , -CH2O - , or -SCH ₂ -; n is 1 ;

p is 1;

m is 0 ;

each of R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ is a hydrogen atom;

the double bond at 2-position of the carbonyl group has E configuration; and

the double bond at 4-position of the carbonyl group has E configuration.

[ 0032]

(0032-1) The compound represented by Formula (1-8) or Formula ( 1-14 ) :

, wherein m is 0 or 1.

(0032-2) The compound represented by Formula (1-8) or

Formula (1-14), wherein m is 0 or 1; and D ¹ is a methyl group.

(0032-3) The compound represented by Formula (1-8) or Formula (1-14), wherein m is 0 or 1; D ¹ is methyl group; and n is 1.

(0032-4) The compound represented by Formula (1-8) or Formula (1-14), wherein .

m is 0 or 1;

D ¹ is a methyl group;

n is 1;

each of R ¹ , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ is a hydrogen atom;

R ² is a hydrogen atom or a methyl group;

the double bond at 2-position of the carbonyl group has E configuration; and

the double bond at 4-position of the carbonyl group has E configuration.

(0032-5) The compound represented by Formula (1-8) or Formula (1-14), wherein

X is a phenyl group, a 3, 4-dichlorophenyl group, a 3- trifluoromethylphenyl group, a 3, 5-difluorophenyl group, a 4-methoxyphenyl group, a 2-pyridyl group, a 3-pyridyl group, a 4-pyridyl group, a 1-naphthyl group, a 2-naphthyl group, a 2-guinolyl group, a 3-quinolyl group, a 4-quinolyl group, a 2-furyl group, a 3-furyl group, a 2-thienyl group, a 3- thienyl group, a 2-benzofuranyl group, a 2-benzothienyl group, a 3 , 4 -methylenedioxyphenyl group, an 1-indanyl group, an 2-indanyl group, a 1- ( 1 , 2 , 3, 4-tetrahydro) naphthyl group, a 2- ( 1 , 2 , 3 , 4-tetrahydro ) naphthyl group, a 2-(3,4- dihydro ) benzopyranyl group, a 3- (3, 4-dihydro) benzopyranyl group, or a 4- (3, 4-dihydro) benzopyranyl group;

r is 0 or 1;

is an oxygen atom;

m is 0 or 1;

D ¹ is a methyl group;

n is i;

each of R ¹ , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ is a hydrogen atom;

R ² is a hydrogen atom or a methyl group;

the double bond at 2-position of the carbonyl group has E configuration; and

the double bond at 4-position of the carbonyl group has E configuration.

(0032-6) The compound represented by Formula (1-8) or. Formula (1-14), wherein

X is a phenyl group, a 3, 4-dichlorophenyl group, a 3- trifluoromethylphenyl group, a 3 , 5-difluorophenyl group, a 4-methoxyphenyl group, a 2-pyridyl group, a 3-pyridyl group, a 4-pyridyl group, a 1-naphthyl group, a 2-naphthyl group, a 2-quinolyl group, a 3-quinolyl group, a 4-quinolyl group, a 2-furyl group, a 3-furyl group, a 2-thienyl group, a 3- thienyl group, a 2-benzofuranyl group, a 2-benzothienyl group, a 3, 4-methylenedioxyphenyl group, an 1-indanyl group, an 2-indanyl group, a 1- ( 1 , 2 , 3 , 4-tetrahydro) naphthyl group, a 2- ( 1 ,·2 , 3 , 4-tetrahydro) naphthyl group, a 2- (3, 4- dihydro) benzopyranyl group, a 3- (3, 4-dihydro) benzopyranyl group, or a 4 -( 3 , 4 -dihydro ) benzopyranyl group;

r is 0;

m is 0 or 1 ;

D ¹ is a methyl group;

n is i;

each of R ¹ , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ is a hydrogen atom;

R ² is a hydrogen atom or a methyl group;

the double bond at 2-position of the carbonyl group has E configuration; and

the double bond at 4-position of the carbonyl group has E configuration.

(0032-7) The compound represented by Formula (1-8) or Formula (1-14), wherein

X is a phenyl group, a 3 , 4 -dichlorophenyl group, a 3- trifluoromethylphenyl group, a 3 , 5-difluorophenyl group, a 4-methoxyphenyl group, a 2-pyridyl group, a 3-pyridyl group, a 4-pyridyl group, a 1-naphthyl group, a 2-naphthyl group, a 2-quinolyl group, a 3-guinolyl group, a 4-quinolyl group, a 2-furyl group, a 3-furyl group, a 2-thienyl group, a 3- thienyl group, a 2-benzofuranyl group, a 2-benzothienyl group, a 3, -methylenedioxyphenyl group, an 1-indanyl group, an 2-indanyl group, a 1- (1, 2, 3, 4-tetrahydro) naphthyl group, a 2- (1, 2, 3, 4-tetrahydro) naphthyl group, a 2- (3, 4- dihydro ) benzopyranyl group, a 3- (3, 4-dihydro) benzopyranyl group, or a 4- (3, 4-dihydro) benzopyranyl group;

r is 1;

W is an oxygen atom;

m is 0 or 1;

D ¹ is a methyl group;

n is 1;

each of R ¹ , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ is a hydrogen atom; ^■

R ² is a hydrogen atom or a methyl group;

the double bond at 2-position of the carbonyl group has E configuration; and

the double bond at 4-position of the carbonyl group has E configuration.

(0032-8) The compound represented by Formula (1-8) or Formula (1-14), wherein

X is a phenyl group, a 2-quinolyl group, a 2-thienyl group, a 3, 4-methylenedioxyphenyl group, or a group represented by Formula (II):

wherein a is 1 or 2, and A ¹ is an oxygen atom or -CH ₂ -, and

each of said groups for X may optionally be substituted with the same or different one or more atoms or groups selected from the group consisting of a C1-C alkyl up which may optionally be substituted with the same different one or more halogen atoms, and a halogen atom; r is 0 or 1;

W is -CH2CH2- or -C (CH ₃ ) 2CH2-;

n is 1 ;

m is 0 ;

each of R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , · R ⁷ and R ⁸ is a hydrogen atom;

the double bond at 2-position of the carbonyl group has E configuration; and

the double bond at 4-position of the carbonyl group has E configuration.

(0032-9) The compound represented by Formula (1-8) or Formula (1-14), wherein

X is a phenyl group, a 2-quinolyl group, a 2-thienyl group, a 3, 4 -methylenedioxyphenyl group, or a group represented by Formula (II):

wherein a is 1 or 2, and A is an oxygen atom or -CH ₂ -, and

each of said groups for X may optionally be substituted with the same or different one or more atoms or groups selected from the group consisting of a C 1-C4 alkyl group which may optionally be substituted with the same or different one or more halogen atoms, and a halogen atom; r is 0 or 1;

W is -CH2CH2 - , -C (CH ₃ ) 2CH2 - , -CH2O - , or -SCH ₂ -;

n is i;

p is 1;

m is 0 ;

each of R ¹ , R ² , R ³ , R ⁴ , _. R ⁵ , R ⁶ , R ⁷ and R ⁸ is a hydrogen atom;

the double bond at 2-position of the carbonyl group has E configuration; and

the double bond at 4-position of the carbonyl group has E configuration.

[ 0033]

(0033-1) The compound represented by Formula (1-5) or Formula (1-13) :

, wherein m is 0 or 1.

(0033-2) The compound represented by Formula (1-5) or Formula (1-13), wherein m is 0 or 1; and D ¹ is a methyl group.

(0033-3) The compound represented by Formula (1-5) or Formula (1-13), wherein m is 0 or 1; D ¹ is a methyl group; and n is 1.

(0033-4) The compound represented by Formula (1-5) or Formula (1-13), wherein

m is 0 or 1;

D ¹ is a methyl group;

n is i;

each of R ¹ , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ is a hydrogen atom;

R ² is a hydrogen atom or a methyl group;

the double bond at 2-position of the carbonyl group has E configuration; and

the double bond at 4-position of the carbonyl group has E configuration.

(0033-5) The compound represented by Formula (1-5) or Formula (1-13), wherein

X is a phenyl group, a 3, -dichlorophenyl group, a 3- trifluoromethylphenyl group, a 3 , 5-difluorophenyl group, a 4 -methoxyphenyl group, a 2-pyridyl group, a 3-pyridyl group, a 4-pyridyl group, a 1-naphthyl group, a 2-naphthyl group, a 2-guinolyl group, a 3-quinolyl group, a 4-quinolyl group, a 2-furyl group, a 3-furyl group, a 2-thienyl group, a 3- thienyl group, a . 2-benzofuranyl group, a 2-benzothienyl group, a 3 , 4 -methylenedioxyphenyl group, an 1-indanyl group, an 2-indanyl group, a 1- ( 1 , 2 , 3 , 4-tetrahydro ) naphthyl group, a 2- (1, 2, 3, -tetrahydro) naphthyl group, a 2- (3, 4- dihydro) benzopyranyl group, a 3- (3, 4-dihydro) benzopyranyl group, or a 4- (3, 4-dihydro) benzopyranyl group;

r is 0 or 1;

W is an oxygen atom;

m is 0 or 1;

D ¹ is a methyl group;

n is 1;

each of R ¹ , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ .and R ⁸ is a hydrogen atom;

R ² is a hydrogen atom or a methyl group;

the double bond at 2-position of the carbonyl group has E configuration; and the double bond at 4-position of the carbonyl group has E- configuration.

(0033-6) The compound represented by Formula (1-5) or Formula (1-13), wherein

X is a phenyl group, a 3 , 4 -dichlorophenyl group, a 3- trifluoromethylphenyl group, a 3 , 5-difluorophenyl group, a 4-methoxyphenyl group, a 2-pyridyl group, a 3-pyridyl group, a 4-pyridyl group, a 1-naphthyl group, a 2-naphthyl group, a 2-guinolyl group, a 3-quinolyl group, a 4-quinolyl group, a 2-furyl group, a 3-furyl group, a 2-thienyl group, a 3- thienyl group, a 2-benzofuranyl group, a 2-benzothienyl group, a 3, 4-methylenedioxyphenyl group, an 1-indanyl group, an 2-indanyl group, a 1- ( 1 , 2 , 3 , 4-tetrahydro) naphthyl group, a 2- (1, 2, 3, -tetrahydro) naphthyl group, _. a 2-(3,4- dihydro) benzopyranyl group, a 3- (3, 4-dihydro) benzopyranyl group, or a 4- (3, 4-dihydro) benzopyranyl group;

r is 0,- rn is 0 or 1;

D ¹ is a methyl group;

n is 1;

each of R ¹ , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ is a hydrogen atom;

R ² is a hydrogen atom or a methyl group;

the double bond at 2-position of the carbonyl group has E configuration; and the double bond at 4-position of the carbonyl group has E configuration.

(0033-7) The compound represented by Formula (1-5) or Formula (1-13), wherein

X is a phenyl group, a 3, 4-dichlorophenyl group, a 3- trifluoromethylphenyl group, a 3 , 5-difluorophenyl group, a 4-methoxyphenyl group, a 2-pyridyl group, a 3-pyridyl group, a 4-pyridyl group, a 1-naphthyl group, a 2-naphthyl group, a 2-quinolyl group, ^' a 3-quinolyl group, a 4-quinolyl group, a 2-furyl group, a 3-furyl group, a 2-thienyl group, a 3- thienyl group, a 2-benzofuranyl group, a 2-benzothienyl group, a 3, 4-methylenedioxyphenyl group, an 1-indanyl group, an 2-indanyl group, a 1- ( 1 , 2 , 3 , 4 -tetrahydro ) naphthyl group, a 2- (1, 2, 3, 4-tetrahydro) naphthyl group, a 2- (3, 4- dihydro) benzopyranyl group, a 3- (3, 4-dihydro) benzopyranyl group, or a 4- (3, 4-dihydro) benzopyranyl group;

r is 1;

W is an oxygen atom;

m is 0 or 1;

D ¹ is a methyl group;

n is i;

each of R ¹ , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ is a hydrogen atom;

R ² is a hydrogen atom or a methyl group;

the double bond at 2-position of the carbonyl group has E configuration; and

the double bond at 4-position of the carbonyl group has E configuration.

(0033-8) The compound represented by Formula (1-5) or Formula (1-13), wherein

X is a phenyl group, a 2-quinolyl group, a 2-thienyl group, a 3 , 4 -methylenedioxyphenyl group, or a group represented by Formula (II) :

wherein a is 1 or 2, and A ¹ is an oxygen atom or -CH ₂ -, and

each of- said groups for X may optionally be substituted with the same or different one or more atoms or groups selected from the group consisting of a C1-C4 alkyl group which may optionally be substituted with the same or different one or more halogen atoms, and a halogen atom; r is 0 or 1;

W is -CH2CH2- or -C (CH ₃ ) 2CH2-;

n is 1;

m is 0 ;

each of R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ is a hydrogen atom; ·

the double bond at 2-position of the carbonyl group has E configuration; and

the double bond at 4-position of the carbonyl group has E configuration.

(0033-9) The compound represented by Formula (1-5) or Formula (1-13), wherein

X is a phenyl group, a 2-quinolyl group, a 2-thienyl group, a 3, -methylenedioxyphenyl group, or a group represented by Formula (II) :

wherein a is 1 or 2, and A ¹ is an oxygen atom or -CH ₂ -, and

each of said groups for X may optionally be substituted with the same or different one or more atoms or groups selected from the group consisting of a C ₁ -C alkyl group which may optionally be substituted with the same or different one or more halogen atoms, and a halogen atom; r is 0 or 1;

W is -CH ₂ CH ₂ -, -C (CH ₃ ) ₂ CH ₂ -, -CH ₂ O-, or -SCH ₂ -;

n is i;

p is 1;

m is 0 ;

each of R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ is a hydrogen atom; the double bond at 2-position of the carbonyl group has E configuration; and

the double bond at 4-position of the carbonyl group has E configuration.

(0033-10) The compound represented by Formula (1-5) or Formula (1-13), wherein

X is a phenyl group, a pyridyl group, a naphthyl group, a 2-quinolyl group, a 2-benzofuranyl group, a 2-thienyl group, a 3, 4-methylenedioxyphenyl group, or a group represented by Formula (II):

wherein a is 1 or 2, and A ¹ is an oxygen atom or -CH ₂ -, and

each of said groups for X may optionally be substituted with the same or different one or more atoms or groups selected from the group consisting of a Ci-C ₄ alkyl group which may optionally be substituted with the same or different one or more halogen atoms, a C1-C4 alkoxy group which may optionally be substituted with the same or different one or more halogen atoms, and a halogen atom; r is 0 or 1;

W is -CH2CH2- , -C CCH ₃ ) 2CH2 - , ^' - CH2O - , or - SCH2 - ;

n is i; p is 1;

m is 0 ;

R ¹ , R ² , R ³ , and R ⁴ are the same or different to each other and are each independently a Ci-C ₄ alkyl group which may optionally be substituted with the same or different one or more halogen atoms, or a hydrogen atom;

each of R ⁵ , R ⁶ , R ⁷ and R ⁸ is a hydrogen atom;

the double bond at 2-position of the carbonyl group has E configuration; and

the double bond at 4-position of the carbonyl group has E configuration compound.

[ 0034]

Next, production processes of the present compound are described.

The present compound can be prepared, for example, according to the following Production Process 1 or Production Process 2.

[ 0035]

Production Process 1

The present compound can be prepared by reacting a compound represented by Formula (4) with a compound represented by Formula (6) in the presence of a condensing agent .

wherein X, Y, W, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , n and r are as defined above.

The ' reaction is carried out in a solvent in the presence of a condensing agent, and if necessary, in the presence of a base.

Examples of the condensing agent used in the reaction include dicyclohexylcarbodiimide, l-ethyl-3- (3- dimethylaminopropyl ) carbodiimide hydrochloride and benzotriazol-l-yloxy-tris (dimethylamino) phosphonium salt.

Examples of the base used in the reaction include: carbonates (for example, sodium carbonate, or potassium carbonate); tertiary amines (for example, triethylamine, diisopropylethylamine, 1 , 8-diazabicyclo[ 5.4.0] undec-7-ene, or 1 , 5-diazabicyclo[ 4.3.0] non-5-ene ) ; and nitrogen- containing aromatic compounds (for example, pyridine, or 4- dimethylaminopyridine ) .

Examples of the solvent used in the reaction include: hydrocarbons (for example, benzene, toluene, or hexane) ; ethers (for example, diethyl ether, or tetrahydrofuran) ; halogenated hydrocarbons (for example, dichloromethane,

1 , 2-dichloroethane, or chlorobenzene) ; and acid amides (for example, IV,I\7-dimethylformamide) .

The reaction time of the reaction is usually within a range of 5 minutes to 72 hrs .

The reaction temperature of the reaction is usually within a range of -20°C to 100°C.

A molar ratio between the compound represented by

Formula (4) and the compound represented by Formula (6) used in the reaction can be set appropriately. Preferably, the ratio, is an equimolar ratio or a _. ratio close thereto.

For example, the amount of the compound represented by Formula (6) is 0.5 to 3 mol relative to 1 mol of the compound represented by Formula (4) ..

The amount of the condensing agent in the reaction can be used usually at an appropriate ratio among 1 mol to an excessive amount, preferably 1 to 3 mol, relative to 1 mol of the compound represented by Formula (4) .

The amount of the base in the reaction can be used usually at an appropriate ratio among 1 mol to an excessive amount, preferably 1 to 3 mol, relative to 1 mol of the compound represented by Formula . (4) .

After completion of the reaction, the present compound can be isolated by a conventional aftertreatment , for example, by mixing the reaction mixture with water followed by an extraction with an organic solvent, and then concentrating the resulting organic layer. In addition, the isolated present compound can be purified by a procedure such as chromatography, recrystallization, distillation, and the like.

[ 0036]

(Production Process 2)

The present compound can be prepared by reacting a compound represented by Formula (5) with the compound represented by Formula (6) in the presence of a base.

wherein Z represents a chlorine atom, a bromine atom or an iodine atom, and W, X, Y, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , r and n are as defined above.

The reaction is carried out in the presence of a base, and usually in the presence of a solvent.

Examples of the base used in the reaction include: carbonates (for example, sodium carbonate, or potassium carbonate); tertiary amines, (for example, triethylamine , diisopropylethylamine, 1 , 8-diazabicyclo[ 5.4.0] undec-7-ene, or 1 , 5-diazabicyclo[ 4.3.0] non-5-ene ) ; and nitrogen- containing aromatic compounds (for example, pyridine, or 4- dimethylaminopyridine ) .

Examples of the solvent used in the reaction include: ethers (for example, 1,4-dioxane, tetrahydrofuran, ethylene glycol dimethyl ether, or tert-butyl methyl ether); aliphatic hydrocarbons (for. example, hexane, heptane, or octane) ; aromatic hydrocarbons (for example, toluene, or xylene); halogenated hydrocarbons (for example, chlorobenzene) ; esters (for example, ethyl acetate, or butyl acetate); nitriles (for example, acetonitrile, or butyronitrile) ; acid amides (for example, N,N- dimethylformamide ) ; sulfoxides (for example, dimethyl sulfoxide); and mixtures thereof.

The reaction time of the reaction is usually within a range of 5 minutes to 72 hrs .

The reaction temperature of the reaction is usually within a range of -20 to 100°C.

A molar ratio between the compound represented by Formula (5) and the compound represented by Formula (6) used in the reaction can be set appropriately. Preferably, the ratio is an equimolar ratio or a ratio close thereto. Specifically, the amount of the compound represented by Formula (6) is 0.5 to 3 mol relative to 1 mol of the compound represented by Formula (5).

The amount of the base in the reaction can be used usually, at an appropriate ratio among 1 mol to an excessive amount, preferably 1 to 3 mol, relative to 1 mol of the compound represented by Formula (5) .

After completion of the reaction, the present compound can be isolated by a conventional aftertreatment , for example, by mixing the reaction mixture with water followed by an extraction with an organic solvent, and then concentrating the resulting organic layer. In addition, the isolated present compound can be purified by a procedure such as chromatography, recrystallization, distillation, and the like.

[ 0037]

Next, production processes of the intermediates of the present compound are described.

[ 0038]

(Reference Production Process 1)

A compound represented by Formula. (5) can be prepared by reacting the compound represented by Formula (4) with a ^' halogenating agent.

wherein W, X, Z, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ and r are as defined above .

The reaction is carried out . in the presence or absence of a solvent .

Examples of the halogenating agent include thionyl chloride, oxalyl chloride and phosphorus oxychloride.

Examples of the solvent used in the reaction include: ethers (for example, 1,4-dioxane, tetrahydrofuran, ethylene glycol dimethyl ether, or tert-butyl methyl ether) ; aliphatic hydrocarbons (for example, hexane, or heptane); aromatic hydrocarbons (for example, toluene, or xylene); halogenated hydrocarbons (for example, chlorobenzene) ; and mixtures thereof.

The reaction time of the reaction is usually within a range of 5 minutes to 24 hrs .

The reaction temperature of the reaction is usually within a range of 0°C to 100°C, but within a range of 0°C to a boiling temperature of the used solvent when the boiling temperature of the solvent is less than 100°C.

The amount of the halogenating agent in the reaction can be used usually at an appropriate ratio among 1 mol to an excessive amount, preferably 1 to 5 mol, relative to 1 mol of the compound represented by Formula (4).

After completion of the reaction, the compound represented by Formula (5) can be isolated by an aftertreatment , for example, by concentrating the reaction mixture. The compound ^' represented by Formula (5) thus isolated can usually be used without purification in the next step, but said compound can be purified if necessary, for example, by distillation etc..

[ 0039]

(Reference Production Process 2)

The compound represented by Formula (4) can be prepared by subjecting a compound represented by Formula (3) to hydrolysis reaction in the presence of a base.

W, X, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ and r are as defined above.

The reaction is carried out in the presence of a base and in the presence of water and an organic solvent.

Examples of the base used in the reaction include alkali metal hydroxide (for example, lithium hydroxide, sodium hydroxide, or potassium hydroxide).

Example of the solvent used in the reaction include ethers (for example, 1,4-dioxane, tetrahydrofuran, ethylene glycol dimethyl ether, or tert-butyl methyl ether) ; aromatic hydrocarbons (for example, toluene, or xylene); halogenated hydrocarbons (for example, chlorobenzene) ; nitriles (for example, acetonitrile , or butyronitrile) ;. alcohols (for example, methanol, ethanol, or propanol); and mixtures thereof.

The reaction time of the reaction is usually within a range of 5 minutes to 72 hrs .

The reaction temperature of the reaction is usually within a range of 0°C to 100°C, but within a range of 0°C to a boiling temperature of the used solvent when the boiling temperature of the solvent is less than 100°C.

The amount of the base in the reaction can be used usually at an appropriate ratio among 1 mol to an excessive amount, preferably 1 to 5 mol, relative to 1 mol of the compound represented by Formula (3) .

After completion of the reaction, the compound represented by Formula (4) can be isolated by an aftertreatment , for example, by adding an acidic water (for example, hydrochloric acid) into the reaction mixture followed by an extraction with an organic solvent, and then drying and concentrating the organic layer. The compound represented by Formula (4) thus isolated can further be purified by chromatography, recrystallization, distillation and the like, or can be used without further other process in the next step.

[ 0040]

(Reference Production Process 3)

A compound represented by Formula (3-1), which is the compound represented by Formula ^' (3) wherein r is 0, can be prepared by reacting the compound represented by Formula

(1) with the compound represented by Formula (2-a) or the compound represented by Formula (2-b) in the presence of a base .

wherein X, Z, R ^a , R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ⁶ are as defined above .

The reaction is carried out in the presence of a base, and usually in a solvent.

Examples of the base used in the reaction include alkali metal alkoxide (for example, sodium methoxide, or potassium tert-butoxide) ; alkali metal hydride (for example, sodium hydride, or potassium hydride) ; and alkali metal amide (for example, sodium bis ( trimethylsilyl ) amide , lithium bis (trimethylsilyl ) amide, or lithium diisopropylamide ) .

Examples of the solvent used in the reaction include hydrocarbons (for example, benzene, toluene, or hexane); ethers (for example, diethyl ether, or tetrahydrofuran) and mixtures thereof.

The reaction time of the reaction is usually within a range of 5 minutes to 72 hrs .

The reaction temperature of the reaction is usually within a range of -80°C to 100°C.

In the reaction, a molar ratio between the compound represented by Formula (1) and the compound represented by Formula (2-a) or the compound represented by Formula (2-b) used in the reaction can be set appropriately. Preferably, the . ratio is an equimolar ratio or a ratio close thereto. Specifically, the amount of the compound represented by Formula (2-a) or the compound represented by Formula (2-b)- is preferably 0.5 to 3 mol relative to 1 mol of the compound represented by Formula (1) .

The amount of the base in the reaction can be used usually at an appropriate ratio among 1 mol to an excessive amount, preferably 1 to 5 mol, relative to 1 mol of the compound represented by Formula (2-a) or the compound represented by Formula (2-b) .

After completion of the reaction, the compound represented by Formula (3-1) can be obtained by a conventional aftertreatment , for example, by mixing the reaction mixture with water followed by an extraction with an organic solvent, and then concentrating the resulting organic layer. The resulting compound represented by Formula (3-1) can further be purified by a procedure such as chromatography, recrystallization, distillation and the like.

[ 0041]

(Reference Production Process 4)

A compound represented by Formula (3-1), which is the compound represented by Formula (3) wherein r is 0, can be prepared by reacting a compound represented by Formula (7) with a compound represented by Formula (8) in the presence of a base.

wherein X, R ^a , R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ⁶ are as defined above .

The reaction is carried out in the presence of a base, and usually in a solvent.

Examples of the base used in the reaction include alkali metal alkoxide (for example, sodium methoxide, or potassium tert-butoxide); alkali metal hydride (for example, sodium hydride, or potassium hydride) ; and alkali metal amide (for example, sodium bis ( trimethylsilyl ) amide , lithium _. bis (trimethylsilyl) amide, or lithium diisopropylamide ) .

Examples of the solvent used in the reaction include hydrocarbons (for example, benzene, toluene, or hexane) ; ethers (for example, diethyl ether, or tetrahydrofuran) and mixtures thereof.

The reaction time of the reaction is _, usually within a range of 5 minutes to 72 hrs.

The reaction temperature of the reaction is usually within a range of -80°C to 100°C.

In the reaction, a molar ratio between the compound represented by Formula (7) and the compound represented by Formula (8) used in the reaction can be set appropriately. Preferably, the ratio is an equimolar ratio or a ratio close thereto. Specifically, the amount of the compound represented by Formula (8) is preferably 0.5 to 3 mol relative to 1 mol of the compound represented by Formula (7) .

The amount of the base in the reaction can be used usually at an appropriate ratio among 1 mol to an excessive, amount, preferably 1 to 5 mol, relative to 1 mol of the compound represented by Formula (8) .

After completion of the reaction, the compound represented by Formula (3-1) can be obtained by a conventional aftertreatment , for example, by mixing the reaction mixture with water followed by an extraction with an organic solvent, and then concentrating the resulting organic layer. The resulting compound represented by Formula (3-1) can further be purified by a procedure such as chromatography, recrystallization, distillation and the like.

[ 0042]

(Reference Production Process 5)

A compound represented by Formula (3-2), which is the present compound represented by Formula (3) wherein r is 1, can be repared, for example, by the following process.

wherein W, X, R ^a , R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ are as defined above .

[ 0043]

(Step 5-1)

A compound represented by Formula (12) can be prepared by reacting the compound represented by Formula (11) with water in the presence of an acid.

The reaction is carried out in the presence of an acid, and in the presence of water and an organic solvent.

Examples of the acid used . in the reaction include inorganic acid (for example, hydrochloric acid, or sulfuric acid); organic acid (for example, methanesulfonic acid, or p-toluenesulfonic acid) .

Examples of the organic solvent used in the reaction include: ethers (for example, 1,4-dioxane, tetrahydrofuran, ethylene glycol dimethyl ether, or tert-butyl methyl ether) ; aromatic hydrocarbons (for example, toluene, or xylene); halogenated hydrocarbons (for example, chlorobenzene) ; nitriles (for example, acetonitrile , or butyronitrile) ; alcohols (for example, methanol, ethanol, or propanol);, ketones (for example, acetone, or methyl isobutyl ketone) and mixtures thereof.

The reaction time of the reaction is usually within a range of 5 minutes to 24 hrs .

The reaction temperature of the reaction is usually within a range of 0°C to 100°C, but within a range of 0°C to a boiling temperature of the used solvent when the boiling temperature of the solvent is less than 100°C.

The amount of the acid used in the reaction can be used usually at an appropriate ratio among 1 mol to an excessive amount relative to 1 mol of the compound represented by Formula (11) .

After completion of the reaction, the compound represented by Formula (12) can be isolated by a conventional aftertreatment , for example, by mixing the reaction, mixture with water followed by an extraction with an organic solvent, and then concentrating the resulting organic layer. The compound represented by Formula (12) thus isolated can be purified by a procedure such as chromatography, recrystallization, distillation,, and the like.

[ 0044]

(Step 5-2)

A compound represented by Formula (3-2) can be prepared by reacting the compound represented by Formula (12) with the compound represented by Formula (8) in the. presence of a base.

The reaction is carried out in the presence of a base, and usually in a solvent.

Examples of the base used in the reaction include alkali metal alkoxide (for example, sodium methoxide, or potassium tert-butoxide) ; alkali metal hydride (for example, sodium hydride, or potassium hydride) ; and alkali metal amide (for example, sodium bis (trimethylsilyl ) amide, lithium bis (trimethylsilyl ) amide, or lithium diisopropylamide ) .

Examples of the solvent used in the reaction include hydrocarbons (for example, benzene, toluene, or hexane) ; ethers (for example, diethyl ether, or tetrahydrofuran) and mixtures thereof.

The reaction time of the reaction is usually within a range of 5 minutes to 72 hrs . The reaction temperature of the reaction is usually within a range of -80°C to 100°C.

In the reaction, a molar ratio between the compound represented by Formula (12) and the compound represented by Formula (8) used in the reaction can be set appropriately. Preferably, the ratio is an equimolar ratio or a ratio close thereto. Specifically, the amount of the compound represented by Formula (8) is preferably 0.5 to 3 mol relative to 1 mol of the compound represented by Formula (12) .

The amount of the base in the reaction can be used usually at an appropriate ratio among 1 mol to an excessive amount, preferably 1 to 5 mol, relative to 1 mol of the compound represented by Formula (12) .

After completion of the reaction, the compound represented by Formula (3-2) can be obtained by a conventional aftertreatment , for example, by mixing the reaction mixture with water followed by an extraction with an organic solvent, and then concentrating the resulting organic layer. The resulting compound represented by Formula (3-2) can further be purified by a procedure such as chromatography, recrystallization, distillation, and the like.

[ 0045]

(Reference Production Process 6) A compound represented by Formula (11-1), which is the compound represented by Formula (11) wherein is an oxygen atom or a sulfur atom, can . be prepared by reacting the compound represented by Formula (9) with, the compound represented by Formula (10) in the resence of a base.

( 1-1)

wherein W ¹ represents an oxygen atom or a sulfur atom, L represents a leaving group such as a chlorine atom, a bromine atom, an iodine atom, a methanesulfonyl group, and the like, and R ^a , X, R ⁴ , R ⁵ and R ⁶ are as defined above.

The reaction is carried out usually in the presence of a base, and usually in a solvent.

Examples of the base used in the reaction include: inorganic base (for example, sodium hydride, sodium hydroxide, potassium hydroxide, or potassium carbonate) ; alkali metal alkoxide (for example, sodium methoxide, or potassium tert-butoxide) ; and organic base (for example, triethylamine, 1 , 4 -diazabicyclo[ 2.2.2] octane, or 1,8- diazabicyclo[ 5.4.0] -7-undecene) .

Examples of the solvent used in the reaction include: ethers (for example, diethyl ether, tetrahydrofuran, or dimethoxyethane) ; acid amides (for example, N,N- dimethylformamide) ; organic sulfurs (for example, dimethyl sulfoxide, or sulfolane) ; aliphatic hydrocarbons (for example, hexane, or heptane); aromatic hydrocarbons (for example, toluene, or xylene); halogenated hydrocarbons (for example, 1 , 2-dichloroethane , or chlorobenzene) ; water; and mixtures thereof.

The reaction time of the reaction is usually within a range of 5 minutes to 72 hrs .

The reaction temperature of the reaction is usually within a range of 0°C to 100°C, but within a range of 0°C to a boiling temperature of the used solvent when the boiling temperature of the solvent is less than 100°C.

In the reaction, a molar ratio between the compound represented by Formula (9) and the compound represented by Formula (10) used in the reaction can be set appropriately.

Preferably, the ratio is an equimolar ratio or a ratio close thereto. For example, the amount of the compound represented by Formula (10) is 1 to 3 mol relative to 1 mol of the compound represented by Formula (9) .

The amount of the base in the reaction can be used usually at an appropriate ratio among 1 mol to an excessive amount, preferably 1 to 3 mol, relative to 1 mol of the compound represented by Formula (10) .

After completion of the reaction, the compound represented by Formula . (11-1) can be isolated by a conventional aftertreatment , for example, by mixing the reaction mixture with water followed by an extraction with an organic solvent, and then concentrating the resulting organic layer. The compound represented by Formula (11-1) thus isolated can be purified by a procedure such as chromatography, recrystallization, distillation, and the like.

[ 0046]

(Reference Production Process 7)

A compound represented by Formula. (3-2-1), which is the present compound represented by Formula (3) wherein r is 1, and is an oxygen atom or a sulfur atom, can be prepared by the following process.

(3-2-1) wherein W ¹ , L, X, Z, R ^a , R ¹ , R ² , R ³ , R , R ⁵ , and R ⁶ are as defined above.

[ 0047] .

(Step 7-1-1)

A compound represented by Formula (16) can be prepared by reacting a compound represented by Formula (14) with the compound represented by Formula (10) in the presence of a base.

The reaction is carried out usually in the presence of a base, and usually in a solvent.

Examples of the base used in the reaction include: inorganic base (for example, sodium hydride, sodium hydroxide, potassium hydroxide, or potassium carbonate) ; alkali metal alkoxide (for example, sodium methoxide, or potassium tert-butoxide) ; and organic base (for example, triethylamine, 1 , 4-diazabicyclo[ 2.2.2] octane, or 1,8- diazabicyclo[ 5.4.0] -7-undecene) .

Examples of the solvent used in the reaction include: ethers (for example, diethyl ether, tetrahydrofuran, or dimethoxyethane) ; acid amides (for example, N,N- dimethylformamide ) ; organic sulfurs (for example, dimethyl sulfoxide, or sulfolane) ; aliphatic hydrocarbons (for example, hexane, or heptane); aromatic hydrocarbons (for example, toluene, or xylene); halogenated hydrocarbons (for example, 1 , 2-dichloroethane, or chlorobenzene) ; water; and mixtures thereof.

The reaction time of the reaction is usually within a range of 5 minutes to 24 hrs .

The reaction temperature of the reaction is usually within a range of 0°C to 100°C, but within a range of 0°C to a boiling temperature of the used solvent when the boiling temperature of the solvent is less than 100°C.

In the reaction, a molar ratio between the compound represented by Formula (14) and the compound represented by Formula (10) used in the reaction can be set appropriately. Preferably, the ratio is an equimolar ratio or a ratio close thereto. For example, the amount of the compound represented by Formula (10) is 1 to 3 mol relative to 1 mol of the compound represented by Formula (14) .

The amount of the base in the reaction can be use.d usually at an appropriate ratio among 1 mol to an excessive amount, preferably 1 to 3 mol, relative to 1 mol of the compound represented by Formula (10).

After completion of the reaction, the compound represented by Formula (16) can be isolated by. a conventional aftertreatment , for example, by mixing the reaction mixture with water followed by an extraction with an organic solvent, and then concentrating the resulting organic layer. The compound represented by Formula (16) thus isolated can be purified by a procedure such as chromatography, recrystallization, distillation, and the like .

[ 0048]

(Step 7-1-2)

The compound represented by Formula (16) can be prepared by reacting a compound represented by Formula (15) with a compound represented by Formula (17) in the presence of a base.

The reaction is carried out usually in the presence of a base, and usually in a solvent.

Examples of the base used in the reaction include: inorganic base (for example, sodium hydride, sodium hydroxide, potassium hydroxide, or potassium carbonate); alkali metal alkoxide (for example, sodium methoxide, or potassium tert-butoxide) ; and organic base (for example, triethylamine, 1 , 4 -diazabicyclo[ 2.2.2] octane, or 1,8- diazabicyclo[ 5.4.0] -7-undecene) . .

Examples of the solvent used in the reaction include: ethers (for example, diethyl ether, tetrahydrofuran, or dimethoxyethane ) ; acid amides (for example, N,N- dimethylformamide) ; organic sulfurs (for example, dimethyl sulfoxide, or sulfolane) ; aliphatic hydrocarbons (for example, hexane, or heptane) ; aromatic hydrocarbons (for example, toluene, or xylene); halogenated hydrocarbons (for example, 1 , 2-dichloroethane, or chlorobenzene) ; water; and mixtures thereof.

The reaction time of the reaction is usually within a range of 5 minutes to 24 hrs .

The reaction temperature of the reaction is usually within a range of 0°C to 100°C, but within a range of 0°C to a boiling temperature of the used solvent when the boiling temperature of the solvent is less than 100°C.

In the reaction, a molar ratio between the compound represented by Formula (15) and the compound represented by Formula (17) used in the reaction can be set appropriately. Preferably, the ratio is derived from an excessive amount of the compound represented by Formula (15) . For example, the amount of the compound represented by Formula (15) is 3 to 5 mol relative to 1 mol of the compound represented by Formula ( 17 ) .

The amount of the base in the reaction can be used usually at an appropriate ratio among 1 mol to an excessive amount, preferably 1 to 3 mol, relative to 1 mol of the compound represented by Formula (15).

After completion of the reaction, the compound represented ^' by Formula (16) can be isolated by a conventional aftertreatment , for example, by mixing the reaction mixture with water followed by an extraction with an organic solvent, and then concentrating the resulting organic layer. The compound represented by Formula (16) thus isolated can be purified by a procedure such as chromatography, recrystallization, distillation, and the like.

[ 0049]

(Step 7-2)

A compound represented by Formula (18) can be prepared by subjecting the compound .represented by Formula (16) to oxidation reaction.

Examples of the oxidation reaction include:

(1) a method using activated manganese dioxide;

(2). a method using pyridinium chlorochromate or pyridinium dichromate;

(3) a method using DMSO oxidation (for example, Swern oxidation) ;

(4) a method using Dess- artin Reagent; and

(5) a method using TEMPO (2, 2, 6, 6-tetramethylpiperidine 1- oxyl ) .

As an example, "(1) a method using activated manganese dioxide" is described specifically.

The reaction is usually carried out in a solvent.

Examples of the solvent used in the reaction include: aliphatic hydrocarbons (for example, hexane, or heptane); aromatic hydrocarbons (for example, toluene, or xylene); halogenated hydrocarbons (for example, dichloromethane, chloroform, 1 , 2-dichloroethane, or chlorobenzene) ; ketones (for example, acetone, or methyl isobutyl ketone).

The reaction time of the reaction is usually within a range of 5 minutes to 24 hrs .

The reaction temperature of the reaction is usually within a range of 0°C to 100°C.

The amount of activated manganese dioxide used in the reaction is usually 1 to 10 parts by weight, preferably 3 to.5 parts by weight, relative to 1 part by weight of the compound represented by Formula (16).

After completion of the reaction, the compound represented by Formula (18) can be isolated by a procedure, for example, by filtering the reaction mixture followed by a concentration procedure. The compound represented by Formula (18) thus isolated can further be purified as necessary by chromatography, recrystallization, distillation, and the like.

[ 0050]

(Step 7-3)

The compound represented by Formula (3-2-1) can be prepared by reacting the compound represented by Formula (18) with the compound represented by Formula (2-a). or the compound represented by Formula (2-b) in the presence of a base.

The reaction is carried out in the presence of a base, and usually in a solvent.

Examples of the base used in the reaction include: alkali metal alkoxide (for example, sodium methoxide, or potassium tert-butoxide) ; alkali metal hydride (for example, sodium hydride, or potassium hydride);- and alkali metal, amide (for example, sodium bis (trimethylsilyl ) amide, lithium bis ( trimethylsilyl ) amide, or . lithium diisopropylamide ) . ^■

Examples of the solvent used in the reaction include hydrocarbons (for example, benzene, toluene, or hexane) ; ethers (for example, diethyl ether, or tetrahydrofuran) ; and mixtures thereof.

The reaction time of the reaction is usually within a range of 5 minutes to 72 hrs .

The reaction temperature of the reaction is usually within a range of -80°C to 100°C.

In the reaction, a molar ratio between the compound represented by Formula (18) and the compound represented by Formula (2-a) or the compound represented by Formula (2-b) used in the reaction can be set appropriately. Preferably, the ratio is an equimolar ratio or a ratio close thereto. Specifically, the amount of the compound represented by Formula (2-a) or the compound, represented by Formula (2-b) is preferably 0.5 to 3 mol relative to 1 mol of the compound represented by Formula (18) .

The amount of the base in the reaction can be used usually at an appropriate ratio among 1 mol to an excessive amount, preferably 1 to 5 mol, relative . to 1 mol of the compound represented by Formula (2-a) or the compound represented by Formula (2-b).

After completion of the reaction, the compound represented by Formula (3-2-1) can be obtained by a conventional aftertreatment , for example, by mixing the reaction mixture with water followed by an extraction with an organic solvent, and then concentrating the resulting organic layer. The resulting compound represented by Formula (3-2-1) can further be purified by a procedure such as chromatography, recrystallization, distillation, and the like .

[ 0051]

(Reference Production Process 8)

The compound represented by Formula (6) can also be prepared, for example, according to the following process.

wherein L, Y, R ⁷ , R ⁸ and n are as defined above.

[ 0052]

(Reference Production Process 9)

The compound represented by Formula (6) can also prepared, for example, according to the following process

wherein L, Y, R ⁷ , R ⁸ and n are as defined above.

[ 0053]

(Step 9-1)

The compound represented by Formula (21) can be prepared by reacting a compound represented by Formula (19) with sodium azide.

The reaction is usually carried out in a solvent.

Examples of the solvent used in the reaction include: ethers (for example, diethyl ether, tetrahydrofuran, or dimethoxyethane) ; acid amides (for example, N,N- dimethylformamide ) ; organic sulfurs (for example, dimethyl sulfoxide, or sulfolane) ; aliphatic hydrocarbons (for example, hexane, or heptane); aromatic hydrocarbons (for example, toluene, or xylene); halogenated hydrocarbons (for example, 1 , 2-dichloroethane, or chlorobenzene) ; water; and mixtures thereof.

The reaction time of the reaction is usually within . a range of 5 minutes to 72 hrs .

The reaction temperature of the reaction is usually within a range of 0°C to 100°C, but within a range of 0°C to a boiling temperature of the used solvent when the boiling temperature of the solv.ent is less than 100°C.

In the reaction, a molar ratio between the compound represented by Formula (19) and sodium azide used in the reaction can be set appropriately. Preferably, the ratio is an equimolar ratio or a ratio close thereto. For example, the amount of the compound represented by Formula (19) is 1 to 3 mol relative to 1 mol of sodium azide.

After completion of the reaction, the compound represented by Formula (21) can be isolated by a conventional aftertreatment , for example, by mixing the reaction mixture with water followed by . an extraction with an organic solvent, and then concentrating the resulting organic layer. The compound represented by Formula (21) thus isolated can be purified by a procedure such as chromatography, recrystallization, distillation, and the like.

[ 0054]

(Step 9-2)

The compound represented by Formula (6) can be prepared by subjecting the compound represented by Formula (21) to reduction reaction.

Examples of the reduction reaction include:

(1) a method using a hydrogenation catalyst, and

(2) a method using metal hydride such as lithium aluminum hydride and the like. As an example, the method using a hydrogenation catalyst is described specifically.

The reaction is carried out , under hydrogen atmosphere, and usually in the presence of a solvent.

Examples of a hydrogenation catalyst used in the reaction include a transition metal compound sush as palladium on carbon, palladium hydroxide, Raney nickel, platinum oxide, and the like.

Examples of the solvent used in the reaction include: alcohols (for example, methanol, ethanol, or propanol); esters (for example, ethyl acetate, or; butyl acetate) ; ethers (for example,, tetrahydrofuran, or 1,4-dioxane) and mixtures thereof.

The reaction is usually carried: out under hydrogen atmosphere at 1 to 100 atm.

The reaction time of the reaction is usually within a range of 5 minutes to 24 hrs .

The reaction temperature of the reaction is usually within a range of -20 to 100°C, but within a range of -20°C to a boiling temperature of the used solvent when the boiling temperature of the solvent is less than 100°C.

The amount of hydrogenation catalyst used in the reaction is usually 0.001 to 0.5 mol relative to 1 mol of the compound represented by Formula (21) .

After completion of the reaction, the compound represented by Formula (6) can be isolated by a procedure, for example, by filtering the reaction mixture followed by a concentration procedure. The compound represented by Formula (6) thus isolated can further be purified as necessary by chromatography, . recrystallization, distillation, and the like.

[ 0055]

(Reference Production Process 10)

A compound represented by Formula (6-1), which is the compound represented by Formula (6) wherein R ⁷ and R ⁸ are a hydrogen atom, can also be prepared, for example, according to the following process.

wherein M represents sodium or potassium, ni represents 0 or 1, and L and Y are as defined above.

[ 0.056]

(Step 10-1)

A compound represented by Formula (22) can be prepared by reacting the compound represented by Formula (19-h) with metal cyanide (MCN) .

The reaction is usually carried out in a solvent.

Examples of metal cyanide used in the reaction include sodium cyanide, and potassium cyanide. Examples of the solvent used in the reaction include: ethers (for example, diethyl ether, tetrahydrofuran, or dimethoxyethane) ; acid amides (for example, N,N- dimethylformamide) ; organic sulfurs (for example, dimethyl sulfoxide, or sulfolane) ; aliphatic hydrocarbons (for example, hexane, or heptane) ; aromatic hydrocarbons (for example, toluene, or xylene); halogenated hydrocarbons (for example, 1 , 2-dichloroethane, or chlorobenzene) ; water; and mixtures thereof.

The reaction time of the reaction is usually within a range of 5 minutes to 24 hrs .

The reaction temperature of the reaction is usually- within a range of 0°C to 100°C.

In the reaction, a molar ratio between the compound represented by Formula (19-h) and the metal cyanide used in the reaction can be set appropriately. Preferably, the ratio is ^■ an equimolar ratio or a ratio close thereto. For example, the amount of the metal cyanide is 1 to 3 mol relative to 1 mol of the compound represented by Formula (19-h) .

After completion of the reaction, the compound represented by Formula (22) can be isolated by a conventional aftertreatment , for example, by mixing the reaction mixture with water followed by an extraction with an organic solvent, and then concentrating the resulting organic layer. The compound represented by Formula (22) thus isolated can be purified by a procedure such as chromatography, recrystallization, distillation, and the like.

[ 0057]

(Step 10-2)

The compound represented by Formula . (6) can be prepared by subjecting the compound represented by Formula (22) to reduction reaction.

Examples of the reduction reaction include:

(1) a method using a hydrogenation catalyst; and

(2) a method using metal hydride such as lithium aluminum hydride.

As an example, the method using a hydrogenation catalyst is described specifically.

The reaction is carried out under hydrogen atmosphere, and usually in the presence of a solvent.

Examples of a hydrogenation catalyst used in the reaction include a transition metal compound such as palladium on carbon, palladium hydroxide, Raney nickel, platinum oxide, and the like.

Examples of the solvent used in the reaction include: alcohols (for example, methanol, ethanol, or propanol); esters (for example, ethyl acetate, or butyl acetate); . ethers (for example, tetrahydrofuran, or 1, 4-dioxane) ; and - mixtures thereof.

The reaction is usually carried out under hydrogen atmosphere at 1 to 100 atm.

The reaction can further be carried out with addition of ammonia as necessary.

The reaction time of the reaction is usually within a range of 5 minutes ^' to 24 hrs .

The reaction temperature of the reaction is usually within a range of -20 to 100°C, but within a range of -20°C to a boiling temperature of the used solvent when the boiling temperature of the solvent is less than 100°C.

The amount of the hydrogenation catalyst used in the reaction is usually 0.001 to 0.5 mol relative to 1 mol of the compound represented by Formula (22) .

After completion of the reaction, the compound represented by Formula (6) can be isolated by a procedure, for example, by filtering the reaction mixture followed by a concentration. The compound represented by Formula (6) thus isolated can further be purified as necessary by chromatography, recrystallization, distillation, and the like.

[ 0058]

The harmful arthropods on which the present compound has a control efficacy include harmful insects and harmful mites. The specifical examples are follows: · Hemiptera:

Delphacidae (for example, Laodelphax striatellus, Nilaparvata lugens, or Sogatella f rcifera) ;

Deltocephalidae (for example, Nephotettix cincticeps, or Nephotettix virescens) ;

Aphididae (for example, Aphis gossypii, or Myzus persicae) ; Pentatomidae (for example, Nezara antennata, Riptortus clavetus, Eysarcoris lewisi, Eysarcoris parvus, Plautia stali, Halyomorpha mista, Stenotus rubrovittatus, or Trigonotylus ruficornis) ;

Aleyrodidae (for example, Trialeurodes vaporariorum, or' Bemisia argentifolii) ;

Coccoidea (for example, Aonidiella aurantii , Comstockaspis perniciosa , Unaspis citri, Ceroplastes rubens, or Icerya purchasi) ;

Tingidae;

Cimicoidea (for example, Cimex lectularius) ,

Psyllidae; and the others;

[ 0059]

Lepidoptera:

Pyralidae (for example, Chilo suppressalis , Cnaphalocrocis medinalis , Notarcha derogata , or Plodia interpunctella) ;

Noctuidae (for example, Spodoptera litura, Pseudaletia separata, Trichoplusia spp . , Heliothis spp., or Helicoverpa spp . ) ; Pieridae (for example, Pieris rapae) ;

Tortricidae (for example, Adoxophyes spp . , Grapholita molesta , or Cydia pomonella) ;

Carposinidae (for example, Carposina niponensis) ;

Lyonetiidae (for example, Lyonetia spp.);

Lymantrlidae (for example, Lymantria spp., or Euproctis spp . ) ;

Yponomeutidae (for example, Plutella xylostella) ;

Gelechiidae (for example, Pectinophora gossypiella) ;

Arctiidae (for example, Hyphantria cunea) ;

Tineidae (for example, Tinea translucens, or Tineola bisselliella) ; and the others;

[ 0060]

Diptera:

House mosquitoes {Culex spp.) (for example, Culex pipiens pallens _r Culex tritaeniorhynchus, or Culex quinquefasciatus) ;

Aedes spp. (for example, Aedes aegypti, or Aedes albopictus) ;

Anopheles spp. (for example, Anopheles sinensis) ;

Chironomidae;

Muscidae (for example, Musca domestica _r or Muscina stabulans) ;

Calliphoridae;

Sarcophagidae; fanniidae;

Anthomyiidae (for example, Delia platura, or Delia antiqua) ;

Agromyzidae (for example, Liriomyza trifolii) ;

Tephritidae;

Drosophilidae;

Phoridae (for example, Megaselia spiracularis) ;

Psychodidae (for example, Clogmia albipunctata) ;

Simuliidae;

Tabanidae;

Stomoxyidae; and the others;

[ 0061]

Coleoptera:

Corn root worms {Diabrotica spp.) (for example, Diabrotica virgifera virgifera , or Diabrotica undecimpunctata howardi) ;

Scarabaeidae (for example, Anomala cuprea, or Anomala rufocuprea;

Curculionxdae (for example, Sitophilus zeamais, Lissorhoptrus oryzophilus, or Callosobruchuys chienensis) ; Tenebrionidae (for example, Tenebrio molitor, or Tribolium castaneum) ;

Chrysomelidae (for example, Oulema oryzae, Aulacophora femoralis, Phyllotreta striolata, or Leptinotarsa decemlineata) ; Dermestidae (for example, Dermestes maculates) ;

Anobiidae;

Epilachna (for example, Epilachna vigintioetopunctata) ;

Lyctidae;

Bostrichidae;

Ptinidae;

Cerambycidae;

Paederus fuscipes; and the others;

[ 0062]

Blattariae:

Blattella germanica, Periplaneta fuliginosa, Periplaneta americana , Periplaneta brunnea , Blatta orientalis , and the others;

[ 0063]

Thysanoptera :

Thrips palmi, Thrips tabaci, Frankliniella occidentalis, Frankliniella intonsa, and the others;

Hymenoptera:

Formicidae (for example, Monomorium pharaosis , Formica fusca japonica , Ochetellus glaber _r Pristomyrmex pungens, or Pheidole noda) ;

Vespidae;

Betylidae;

Tenthredinidae (for example, Athalia japonica) ; [ 0064]

Orthoptera :

Gryllotalpidae, Caelifera, Grylloidea, and the others;

Siphonaptera :

Ctenocephalides felis, Ctenocephalides canis, Pulex irritans, Xenopsylla cheopis, and the others;

Anoplura:

Pediculus humanus corporis , Phthirus pubis, Haematopinus eurysternus , Dalmalinia ovis, Haematopinus suis, and the others;

Isoptera:

Subterranean termites (for example, Reticulitermes speratus, Coptotermes formosanus, Reticulitermes flavipes ,

Reticulitermes hesperus, Reticulitermes virginicus , Reticulitermes tibialis, or Heterotermes aureus) ;

Dry wood termites (for example, Incisitermes minor);

Damp wood termites (for example, Zootermopsis nevadensis) ; and the others;

[ 0065]

Acarina:

Tetranychidae (for example, Tetranychus urticae, Tetranychus kanzawai , Panonychus citri, Panonychus ulmi, or Oligonychus sp . ) ;

Eriophyidae (for example, Aculops lycopers , Aculops pelekassi , or Aculus schlechtendali) ; Tarsonemidae (for example, _. Polyphagotarsonemus latus);

Tenuipalpidae;

Tuckerellidae;

Ixodidae (for example, . Haemaphysalis longicornis , Haemaphysalis flava, Dermacentor variabilis , Haemaphysalis flava, . Dermacentor taiwanicus , Ixodes ovatus, Ixodes persulcatus, Ixodes scapularis, Boophilus microplus , Amblyomma a ericanum, or Rhipicephalus . sanguineus) ;

Acaridae (for example, Tyrophagus putrescentiae);

Pyroglyphidae (for example, Dermatophagoides farinae, or Dermatophagoides ptrenyssnus) ;

Cheyletidae (for example, Cheyletus eruditus , Cheyletus malaccensis, or Cheyletus moorei) ;

Dermanyssidae (for example, Ornithonyssus bacoti, Ornithonyssus sylvairum, or Dermanyssus gallinae) ;

Trombiculidae (for example, Leptotrombidium akamushi) ; and the others;

Araneae :

Chiracanthium japonicum, Latrodectus hasseltii, and the others;

[ 0066]

Chilopoda :

Thereuonema hilgendorfi , Scolopendra subspinipes, and the others;

Diplopoda: Oxidus gracilis , Nedyopus tambanus, and the others;

Isopoda:

Armadillidium vulgare, and the others;

Gastropoda :

Limax marginatus, Limax flavus, and the others.

[ 0067]

The agent for controlling harmful arthropods of the present invention comprises the present compound and an inert carrier. The agent for controlling harmful arthropods of the present invention is usually prepared by mixing the present compound with an inert carrier such as a solid carrier, a liquid carrier, a gas carrier, and if necessary, adding surfactant, or other pharmaceutical additives, and then formulating into the form of emulsifiable concentrate, oil solution, dust formulation, granular formulation, wettable powder, flowable formulation, microcapsule formulation, aerosol, fumigant, toxic bait, resin formulation, and so on. These formulations usually comprise 0.01 to 95% by weight of the present compound.

[ 0068]

Examples of the solid carrier used in the formulation include a powdered or granulated solid carrier such as clays (for example, kaolin clay, diatomaceous earth, bentonite, Fubasami clay, or acid clay) , synthetic hydrous silicon oxide, talc, ceramic, other inorganic minerals (for example, sericite, quartz, sulfur, active carbon, calcium carbonate, or hydrated silica), chemical fertilizer (for example, ammonium sulfate, ammonium phosphate, ammonium nitrate, urea, or ammonium chloride), and the others.

[ 0069]

Examples of the liquid carrier include water, alcohols (for example, methanol, ethanol, isopropyl alcohol, butanol, hexanol, benzyl alcohol, ethylene glycol, propylene glycol, or phenoxyethanol ) , ketones (for example, acetone, methyl ethyl ketone, or cyclohexanone) , aromatic hydrocarbons (for example, toluene, xylene,: ethylbenzene, dodecylbenzene, phenylxylylethane, or methylnaphthalene ) , aliphatic hydrocarbons (for example, hexane, cyclohexane, kerosene, or light oil), esters (for example, ethyl acetate, butyl acetate, isopropyl myristate, ethyl oleate, diisopropyl adipate, diisobutyl adipate, or propyleneglycol monomethylether acetate), nitriles (for example, acetonitrile , or isobutyronitrile ) , ethers (for example, diisopropyl ether, 1,4-dioxane, ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, diethylene glycol monomethyl . ether, propylene glycol monomethyl ether, dipropylene glycol monomethyl ether, or 3-methoxy-3-methyl- l-butanol) ,. acid amides (for example, W,N-dimethylformamide, or A^N-dimethylacetamide) , halogenated hydrocarbons (for example, dichloromethane, trichloroethane, or carbon tetrachloride), sulfoxides (for example, dimethyl sulfoxide), propylene carbonate and vegetable oil (for example, soybean oil, or cottonseed oil) .

[ 0070]

Examples of the gas carrier include fluorocarbon, butane gas,, LPG (liquefied petroleum gas), dimethyl ether and carbon dioxide .

[ 0071]

Examples of the surfactant include a non-ionic surfactant (for example, polyoxyethylene alkyl ether, polyoxyethylene alkylaryl ether,, or polyethylene glycol fatty acid ester), and an anionic surfactant (for example, alkylsulfonate, alkylbenzenesulfonate, or alkylsulfate ) .

[ 0072]

Examples of other pharmaceutical additives include sticking agent, dispersing agent, coloring agent and stabilizing agent, specifically, casein, gelatin, sugars (for example, starch, arabic gum, cellulose derivative, or alginic acid) , lignin derivative, bentonite, synthetic water-soluble polymer (for example, polyvinyl alcohol, polyvinylpyrrolidone, or polyacrylic acids), PAP (isopropyl acid phosphate), BHT (2, 6-di- tert-butyl-4- methylphenol ) , and BHA(an mixture of 2- tert-butyl-4 - methoxyphenol and 3-tert-butyl-4-methox.yphenol) .

[ ΟΟ73] The method for controlling harmful arthropods of the present invention comprises applying an effective amount of the present compound to harmful arthropods or a place where the harmful arthropods live. For the method for controlling harmful arthropods of the present invention, the present compound is usually used in the form of an agent for controlling harmful arthropods of the present invention.

[-0074]

Examples of the place where the harmful, arthropods live include paddy fields, fields, orchards, non- agricultural lands, and houses.

Any conventional application technique can be used to apply the present compound, as long as the present compound can contact harmful arthropods or can be taken by harmful arthropods by using the application technique.

Examples of the application technique include sparging treatment, soil treatment, application to seeds, and water culture medium treatment.

[ 0075]

When the agent for controlling harmful arthropods of the present invention is used in order to control harmful arthropods in agriculture, the application dose as an amount of the present compound is usually within a range of 1 to 10,000 g per 10,000 m ² . The. emulsifiable concentrate, the wettable powder, or the flowable formulation etc. of the agent for _. controlling harmful arthropods of the present invention . is usually applied by diluting it with water in such a way that a concentration of the active ingredient is within a range of 0.01 to 10,000 ppm, and then sparging it.

The granular formulation, or the dust formulation etc., is usually applied as itself without diluting it.

[ 0076]

These formulations or a water dilution thereof can directly be sparged to harmful arthropods or plants such as crops to be protected from harmful arthropods, and also can be used to treat the soil of crop land in order to control harmful arthropods which live there.

[ 0077]

A sheeted or corded resin formulation can be used in order to control harmful arthropods by wrapping crops with it, by hanging it near crops, by covering soils around plant foot with it, etc..

[ 0078]

When the agent for controlling harmful arthropods of the present invention is used to control harmful arthropods which live inside a house, the application dose as an amount of the present compound is usually within a range of 0.01 to 1,000 mg per 1 m ² of an area to be treated, in the case of using it on a planar area. In the case of using it spatially, the application dose as an amount of the present compound is usually within a range of 0.01 to 500 mg per 1 m ³ of the space to be treated.

The emulsifiable concentrate, the wettable powder, or the flowable formulation etc. of the agent for controlling harmful arthropods of the present invention, is usually applied after diluting it with water in such a way that a concentration of the active ingredient is within a range of 0.1 to 1,000 ppm, and then sparging it.

The oil solution, aerosol, fumigant, toxic bait etc., is usually applied as itself without diluting it.

[ 0079]

The present compound can be used in agricultural lands where the following ''Plants'' are cultivated.

Crops :

corn, rice, wheat, barley, rye, oat, sorghum, cotton, soybean, peanut, buckwheat, beet, rapeseed, sunflower, sugar cane, tobacco, and the others;

Vegetables:

solanaceous vegetables (for example, eggplant, tomato, bell pepper, pepper or potato) , .

cucurbitaceous vegetables (for example, cucumber, pumpkin, zucchini, water melon or melon) ,

cruciferous vegetables (for example, Japanese radish, white turnip, horseradish, kohlrabi, Chinese cabbage, cabbage, leaf mustard, broccoli or cauliflower) ,

asteraceous vegetables (for example, burdock, crown daisy, artichoke or lettuce) ,

liliaceous vegetables (for example, green onion, onion, garlic or asparagus),

ammiaceous vegetables (for example, carrot, parsley, celery or parsnip) ,

chenopodiaceous vegetables (for example, spinach or Swiss chard),

lamiaceous vegetables (for example, Perilla frutescens, mint or basil ) ,

strawberry, sweet potato, Dioscorea japonica, colocasia or the others;

flowers;

ornamental foliage plants;

Fruits:

pomaceous fruits (for example, apple, pear, Japanese pear, Chinese quince or quince) ,

stone fleshy fruits (for example, peach, plum, nectarine, Prunus mume, cherry fruit, apricot or prune),

citrus fruits (for example, Citrus unshiu, orange, lemon, lime or grapefruit),

nuts (for example, chestnut, walnuts, hazelnuts, almond, pistachio, cashew nuts or macadamia nuts), berry fruits (for example, blueberry, cranberry, blackberry or raspberry) ,

grape, kaki persimmon, olive, Japanese plum, banana, coffee, date palm, coconuts, and the others;

Trees other than fruit trees:

tea, mulberry, flowering plant,

roadside trees (for example, ash, birch, dogwood, Eucalyptus, Ginkgo biloba, lilac, maple, Quercus, poplar, Judas tree, Liquidambar formosana, plane tree, zelkova, Japanese arborvitae, fir wood, hemlock, juniper, Pinus, Picea, or Taxus cuspidate) , and the others.

[ 0080]

The above-mentioned ' ' Plants ' ¹ includes genetically modified plants.

[ 0081]

The agent for controlling harmful arthropods of the present invention may be used as a mixture with or in combination with other insecticide, miticide, nematicide, fungicide, plant growth regulator, herbicide, synergist and the like.

Examples of the active ingredient of said insecticide, miticide,, nematicide, fungicide, plant growth regulator, herbicide and synergist include as follows.

[ 0082]

Active ingredient of Insecticide: (1) Organophosphorus compound

acephate, Aluminium 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, and cadusafos.

(2) Carbamate compound

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) Pyrethroid compound

acrinathrin, allethrin, benfluthrin, beta-cyfluthrin, bifenthrin, cycloprothrin, cyfluthrin, cyhalothrin, cypermethrin, deltamethrin, esfenvalerate, ethofenprox, fenpropathrin, fenvalerate, flucythrinate , flufenoprox, flumethrin, fluvalinate, halfenprox, imiprothrin, permethrin, prallethrin, pyrethrin, resmethrin, sigma- cypermethrin, silafluofen, tefluthrin, tralomethrin, transfluthrin, tetramethrin, phenothrin, cyphenothrin, alpha-cypermethrin, zeta-cypermethrin, lambda-cyhalothrin, gamma-cyhalothrin, furamethrin, tau-fluvalinate, metofluthrin, profluthrin, . dimefluthrin, 2,3,5,6- tetrafluoro-4- (methoxymethyl ) benzyl (EZ) - (IRS, 3RS; IRS, 3SR) - 2, 2-dimethyl-3-prop-l-enylcyclopropanecarboxylate, 2,3,5,6- tetrafluoro-4 -methylbenzyl ( EZ) - (IRS, 3RS; IRS, 3SR) -2,2- dimethyl-3-prop-l-enylcyclopropanecarboxylate, and 2,3,5,6- tetrafluoro-4- (methoxymethyl) benzyl ( IRS, 3RS; IRS, 3SR) -2 , 2- dimethyl-3- (2-methyl-l-propenyl ) cyclopropanecarboxylate . (4) Nereistoxin compound

cartap, bensultap, thiocyclam, monosultap, and bisultap.

(5) Neonicotinoid compound

imidacloprid, nitenpyram, acetamiprid, thiamethoxam, thiacloprid, dinotefuran, and clothianidin .

(6) Benzoyl urea compound

chlorfluazuron, bistrifluron, diafenthiuron, diflubenzuron, fluazuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron, triflumuron, and triazuron.

(7) Phenylpyrazole compound

acetoprole, ethiprole, fipronil, vaniliprole, pyriprole, and pyrafluprole .

(8) Bt-toxin

Live spores derived from Bacillus thuringiensis and Crystal toxin produced by Bacillus thuringiensis, and a mixture thereof.

(9) Hydrazine compound

chromafenozide, halofenozide, methoxyfenozide , and tebufenozide .

(10) Organochlorine compound

aldrin, dieldrin, dienochlor, endosulfan, and methoxychlor .

(11) Active ingredient of Other insecticide

machine oil, nicotine-sulfate , avermectin-B, bromopropylate, buprofezin, chlorphenapyr, cyantraniliprole, cyromazine, D-D ( 1 , 3-Dichloropropene ) , emamectin-benzoate, fenazaguin, flupyrazofos , hydroprene, methoprene, indoxacarb, metoxadiazone, milbemycin-A, pymetrozine, pyridalyl, pyriproxyfen, spinosad, sulfluramid, tolfenpyrad, triazamate, flubendiamide, lepimectin, Arsenic acid, benclothiaz, Calcium cyanamide, lime sulfur (Calcium polysulfide) , chlordane, DDT, DSP, flufenerim, flonicamid, flurimfen, formetanate, metam-ammonium, _. metam-sodium, Methyl bromide, Potassium oleate, protrifenbute, spiromesifen, sulfoxaflor, Sulfur, metaflumizone, spirotetramat, pyrifluquinazone, spinetoram, chlorantraniliprole, tralopyril, cyantraniliprole .

[ 0083]

Active ingredient of Miticide:

acequinocyl, amitraz, benzoximate, bifenaate, bromopropylate , chinomethionat , 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 .

[ 0084]

Active ingredient of Nematicide:

DCIP, fosthiazate, levamisole hydrochloride ( levamisol ) , methyl isothiocyanate , morantel tartarate, and imicyafos .

[ 0085]

Active ingredient of Fungicide:

azole fungicidal compound (for example, propiconazole, prothioconazole, triadimenol, prochloraz, penconazole, tebuconazole, flusilazole, diniconazole, bromuconazole, epoxiconazole, difenoconazole, cyproconazole , metconazole, triflumizole, tetraconazole, myclobutanil , fenbuconazole, hexaconazole, fluquinconazole, triticonazole, bitertanol, imazalil, flutriafol, and the like);

cyclic amine fungicidal compound (for example, fenpropimorph, tridemorph, fenpropidin, and the like) ;

benzimidazole fungicidal compound (for example, carbendezim, benomyl, thiabendazole, thiophanate-methyl , and the like) ;

procymidone; cyprodinil; pyrimethanil ; diethofencarb; thiuram; fluazinam; mancozeb; iprodione; vinclozolin; chlorothalonil ; captan; mepanipyrim; fenpiclonil; fludioxonil; dichlofluanid; folpet; . kresoxim-methyl ; azoxystrobin; trifloxystrobin; . fluoxastrobin; picoxystrobin; pyraclostrobin; dimoxystrobin; pyribencarb; spiroxamine; quinoxyfen; fenhexamid; famoxadone; fenamidone; zoxamide; ethaboxam; amisulbrom; iprovalicarb; benthiavalicarb; cyazofamid; mandipropamid; boscalid; penthiopyrad; metrafenone; fluopiran; bixafen; cyflufenamid; proquinazid; isotianil; and tiadinil.

[ 0086]

Active ingredient of Herbicide:

(1) Phenoxy fatty acid herbicidal compound

2,4-PA, MCP, CPB, phenothiol, mecoprop, fluroxypyr, triclopyr, clomeprop, and naproanilide .

(2) Benzoate herbicidal compound 2,3,6-TBA, dicamba, clbpyralid, picloram, aminopyralid, quinclorac, and quinmerac. (3) Urea herbicidal compound diuron, linuron, chlortoluron, isoproturon, fluometuron, isouron, tebuthiuron, methabenzthiazuron, cumyluron, daimuron, and methyl-daimuron .

(4) Triazine herbicidal compound

atrazine, ametoryn, cyanazine, simazine, propazine, simetryn, dimethametryn, prometryn, metribuzin, triaziflam, and indaziflam.

(5) Bipyridinium herbicidal compound

paraquat, and diquat.

(6) Hydroxybenzonitrile herbicidal compound

bromoxynil, and ioxynil.

(7) Dinitroaniline herbicidal compound

pendimethalin, prodiamine, and trifluralin.

(8) Organophosphorus herbicidal compound

amiprofos-methyl , butamifos, bensulide, piperophos, anilofos, glyphosate, glufosinate, glufosinate-P, and bialaphos .

(9) _. Carbamate herbicidal compound

di-allate, tri-allate, EPTC, butylate, benthiocarb, esprocarb, molinate, dimepiperate, swep, chlorpropham, phenmedipham, phenisopham, pyributicarb, and asulam.

(10) Acid amide herbicidal compound

propanil, propyzamide, bromobutide, and etobenzanid. (11) Chloroacetanilide herbicidal compound

acetochlor, alachlor, butachlor, dimethenamid, propachlor, metazachlor, metolachlor, pretilachlor, thenylchlor, and pethoxamid.

(12) Diphenyl ether herbicidal compound

acifluorfen-sodium, bifenox, oxyfluorfen, lactofen, fomesafen, chlomethoxynil, and aclonifen.

(13) Cyclic imide herbicidal compound

oxadiazon, cinidon-ethyl , carfentrazone-ethyl , surfentrazone , flumiclorac-pentyl , flumioxazin, pyraflufen- ethyl, oxadiargyl,' pentoxazone, fluthiacet-methyl , butafenacil, benzfendizone, bencarbazone, and saflufenacil .

(14) Pyrazole herbicidal compound

benzofenap, pyrazolate, pyrazoxyfen, topramezone, and pyrasulfotole .

(15) Triketone herbicidal compound

isoxaflutole, benzobicyclon, sulcotrione, mesotrione, tembotrione, and tefuryltrione .

(16) Aryloxyphenoxypropionate herbicidal compound

clodinafop-propargyl , cyhalofop-butyl , diclofop-methyl , fenoxaprop-ethyl ) , fluazifop-butyl , haloxyfop-methyl , and quizalofop-ethyl, metamifop.

(17) Trione oxime herbicidal compound

alloxydim-sodium, sethoxydim,. butroxydim, clethodim, cloproxydim, cycloxydim, tepraloxydim, tralkoxydim, and profoxydim.

(18) Sulfonyl urea herbicidal compound

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, ethamets.ulfuron-methyl , triflusulfuron-methyl , flazasulfuron, cyclosulfamuron, flupyrsulfuron, sulfosulfuron, azimsulfuron, ethoxysulfuron, oxasulfuron, iodosulfuron-methyl-sodium, foramsulfuron, mesosulfuron-methyl , trifloxysulfuron, tritosulfuron, orthosulfamuron, flucetosulfuron, and propyrisulfuron .

(19) Imidazolinone herbicidal compound

imazamethabenz-methyl , imazamethapyr, imazamox, imazapyr, imazaquin, and imazethapyr.

(20) Sulfonamide herbicidal compound

flumetsulam, metosulam, diclosulam, florasulam, cloransulam-methyl , penoxsulam, and pyroxsulam.

(21) Pyrimidinyloxybenzoate herbicidal compound

pyrithiobac-sodium, bispyribac-sodium, pyriminobac- methyl, pyribenzoxim, pyriftalid, and pyrimisulfan .

(22) Oter herbicidal compound

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, pyraclonil, pyroxasulfone , thiencarbazone-methyl , aminocyclopyrachlor , ipfencarbazone, and methiozolin) .

[ 0087]

Active ingredient of Synergist

piperonyl butoxide, sesamex, < sulfoxide, N- (2- ethylhexyl ) -8 , 9, lQ-trinorborn-5-ene-2 , 3-dicarboximide ( GK 264), N-declyimidazole, WARF-antiresistant , TBPT, TPP, IBP, PSCP, methyl iodide (CH ₃ I ) , t-phenylbutenone , diethylmaleate, DMC, - FDMC, ETP, and ETN .

EXAMPLES

[ 0088]

The following Production Examples, Formulation Examples and Test Examples serve to illustrate the present invention in more detail, which should not intend to limit the present invention.

[ 0089]

Production Examples of the present compound are shown below. [ 0090]

Production Example 1

To tetrahydrofuran (30 mL) were added (2£, 4£)-6- phenyl-hexa-2 , 4 -dienoic acid (435 mg, 2.31 mmol) ^' and ( tetrahydrofuran-2-yl ) -methylamine (233 mg, 2.31 mmol), and to the mixture was then added l-ethyl-3- ( 3- dirnethylaminopropyl ) carbodiimide hydrochloride (443 mg, 2.31 mmol) under ice-cooling. The mixture was stirred at room temperature for 12 hrs . To a mixture of 5% hydrochloric acid (20 mL) and iced water (50 mL) was poured the reaction mixture, and the resulting mixture was extracted twice with ethyl acetate (100 mL) . The combined ethyl acetate layers were washed with saturated aqueous sodium bicarbonate (50 mL) followed by saturated brine (50 mL) , and the organic layer was dried over magnesium sulfate The organic layer was concentrated under reduced pressure. The resultant residue was purified by silica gel column chromatography to give (2E, E) -N- (tetrahydrofuran-2- ylmethyl ) -6-phenyl-hexa-2 , 4-dienamide (220 mg) represented by the following formula:

(hereinafter referred to as ' 'the present compound

[ 0091] The present compound (1) :

¹ H-NMR (CDCI3, TMS) 5(ppm) : 7.16-7.32 ( 6H, m) , 6.16-6.22 (2H, m) , 5.78(1H, m) , 5.60(1H, brs) , 3.86(1H, td) , 3.83(1H, dd) , 3.74(1H, dd) , 3.55(1H, dd) 3.50(2H, t), 3.22-3.38 ( 1H, m) , 1.88-2.01 (2H, m) , 1.53-1.58 ( 2H, m)

[ 0092]

Production Example 2

(2E, 4£) -N- (Tetrahydrofuran-2-ylmethyl ) -8-phenyl-octa- 2 , 4-dienamide represented by ^' the following formula:

(hereinafter referred to as ^{1 1} the present compound (2) ' ¹ ) was prepared in a manner similar to Production Example 1 by using ( 2E, 4E) -8-phenyl-octa-2 , 4 -dienoic acid instead of (2£, E) -6-phenyl-hexa-2 , 4-dienoic acid.

[ 0093]

The present compound -(2) :

¹ H-NMR (CDCI ₃ , TMS) δ(ρρπι) : 7.28(1H, d) , 7.16-7.30 ( 5H, brs), 6.08-6.14 (2H, m) , 5.76(1H, m) , 5.73(1H, brs), 3.86(1H, td) , 3.-82 (1H, dd), 3.74(1H, dd) , 3.55(1H, dd) , 3.23(1H, m) , 2.62(2H, t), 2.18(2H, q) , 1.82-1.98 (2H, m) , 1.76(2H, m) , 1.56(2H, m)

[ 0094]

Production Example 3 (2E, AE) -N- (Tetrahydrofuran-2-ylmethyl) -8- (3,

dichlorophenyl ) -octa-2 , 4-dienamide represented

following formula:

(hereinafter referred to as ' 'the present compound (3) ¹ ') was prepared in a manner similar to Production Example 1 by using (2£, E) -8- (3, -dichlorophenyl ) -octa-2, 4-dienoic acid instead of (2E, AE) -6-phenyl-hexa-2 , 4-dienoic acid.

[ 0095]

The present compound (3) :

¹ H-NMR (CDC1 ₃ , TMS) δ(ρρπι) : 7.16-7.35 ( 3H, m) , 7.02 (1H, d) , 6.06-6.13 (2H, m) , 5.79(1H, brs), 5.76(1H, d) , 3.87(1H, td) , 3.85(1H, dd), 3.75(1H, dd) , 3.65(1H, dd) , 3.24(1H, m) , 2.55(2H, t), 2.17(2H, m) , 1.82-1.98 ( 2H, m) , 1.70(2H _f m) , 1.60(2H, m)

[ 0096]

Production Example A

(2E, AE) -N- (Tetrahydrofuran-2-ylmethyl) -8- (3, 4- methylenedioxyphenyl ) -octa-2 , 4-dienamide represented by the following formula: (hereinafter referred to as ' 'the present compound (4) ' ') was prepared in a manner similar to Production Example 1 by using (2E, AE) -8- (3, 4 -methylenedioxyphenyl ) -octa-2, 4-dienoic acid instead of ( 2E, AE) -6-phenyl-hexa-2 , 4-dienoic acid .

[ 0097]

The present compound (4) :

¹ H-NMR (CDC1 ₃ , TMS) δ (ppm) : 7.23 (1H, t), 6.59-6.73 (3H, m) , 6.08-6.13 (2H, m) , 5.92.(2H, s), 5.76(1H, m) , 5.73(1H, brs), 3.98(1H, td), 3.84(1H, dd) , 3.74(1H, dd), 3.55(1H, dd) , 3.23(1H, m) , 2.52(2H, t), 2.18(2H, q) , 1.88-2.04 (2H, m) , 1.76 (2H, m) , 1.55 (2H, m)

[ 0098]

Production Example 5

(2E, E) -N- (Tetrahydrofuran-3-ylmethyl ) -6-phenyl-hexa- 2 , 4-dienamide represented by the following formula:

(hereinafter referred to as ' 'the present compound (5) ' ') was prepared in a manner similar to Production Example 1 by using ( tetrahydrofuran-3-yl ) -methylamine instead of

(tetrahydrofuran-2-yl ) -methylamine .

[ 0099]

The present compound (5) :

¹ H-NMR (CDCI3, TMS) 5(ppm) : 7.16-7.32 ( 5H, m) , 6.16-6.24 (2H, m) , 5.78(1H, m) , 5.60 ( 1H, brs ) , 3.89(1H, td) , 3.82(1H, dd) , 3.73(1H, dd) , 3.55(1H, dd) , 3.33-3.41 ( 3H, m) , 2.50(1H, m) , 2.08(1H, m) , 1.65(2H, m)

[ 0100]

Production, Example 6

(22?, AE) -N- (Tetrahydrofuran-3-ylmethyl) -8-phenyl-octa- 2, 4-dienamide represented by the following formula:

(hereinafter referred to as ' 'the present compound (6) '.') was prepared in a manner similar to Production Example 1 by using (22?, AE) -8-phenyl-octa-2 , 4-dienoic acid instead of (22?, 42?) -6-phenyl-hexa-2 , 4-dienoic acid, and by using (tetrahydrofuran-3-yl ) -methylamine instead of

(tetrahydrofuran-2-yl ) -methylamine .

[ 0101]

The present compound (6) :

¹ H-N R (CDCI ₃ , TMS) 5(ppm) : 7.28 (1Η,· d) , 7.16-7.20 ( 5H, brs), 6.09(2H, m) , 5.77(1H, m) , 5.73(1H, brs ) , 3.89 ( 1H, td) , 3.8K1H, dd), 3.74(1H, dd) , 3.55(1H, dd) ,. 3.35-3.38 (2H, m) , 2.60-2.64 (2H, t), 2.16(2H, q) , 2.02-2.08 ( lH, m) , 1.74- 1.77(2H, m) , 1.62-1.65 ( 2H, m)

[ 0102]

Production Example 7 (2E, AE) -N- (Tetrahydrofuran-3-ylmethyl) -8- (3,

dichlorophenyl ) -octa-2, 4-dienamide represented

following formula:

(hereinafter referred to as ' 'the present compound (7) ' ') was prepared in a manner similar to Production Example 1 by using (2E, AE) -8- (3, 4-dichlorophenyl ) -octa-2, 4-dienoic acid instead of (2E, E) -6-phenyl-hexa-2 , 4-dienoic acid, and by using (tetrahydrofuran-3-yl ) -methylamine instead of

( tetrahydrofuran-2-yl ) -methylamine.

[ 0103]

The present compound (7) :

¹ H-N R (CDCI3, TMS) 5(ppm) : 7.16-7.27 (2H, m) , 7.02 (1H, d) , 6..07-6.13 (2H, m) , 5.76(1H, m) , 5.73(1H, brs ) , 3.89(1H, td) , 3.82(1H, dd) , 3.74(1H, dd) , 3.55(1H, dd) , 3.33-3.41 ( 3H, m) , 2.50-2.59 (2H, t) , 2.17(2H, g) , 2.08(1H, m) , 1.69(2H, m) , 1.62-1.64 (2H, m)

[ 0104]

Production Example 8

{2E, AE) -N- (Tetrahydrofuran-3-ylmethyl) -8- (3- trifluoromethylphenyl ) -octa-2, -dienamide represented by the following formula:

(hereinafter referred to as ' 'the present compound (8) ' ' ) was prepared in a manner similar to Production Example 1 by using [2E, E) -8- (3-trifluoromethylphenyl ) -octa-2, -dienoic acid instead of (2£, 4Ε) -6-phenyl-hexa-2, 4-dienoic acid, and by using (tetrahydrofuran-3-yl) -methylamine instead of

( tetrahydrofuran-2-yl ) -methylamine .

[ 0105]

The present compound (8) :

¹ H-NMR (CDC1 ₃ , TMS) 5(ppm) : 7.33-7.46 ( H, m) , 6.09(2H, m) , 5.77 (1H, m) , 5.73(1H, brs), 3.89(1H, td) , 3.82(1H, dd), 3.73(1H, dd), 3.55(1H, dd) , 3.37(2H, t), 2.68(2H, t), 2.18(2H, q) , 2.02(1H, m) , 1.78(2H, m) , 1.54-1.64 (2H, m)

[ 0106]

Production Example 9

(2E, 4£) -N- (Tetrahydrofuran-3-ylmethyl) -8- (3, 5- difluorophenyl ) -octa-2, 4-dienamide represented by the following formula:

(hereinafter referred to as ' 'the present compound (9) ' ') was prepared in a manner similar to Production Example 1 by using {2E, AE) -8- (3, 5-difluorophenyl) -octa-2, 4-dienoic acid instead of ( 2E, AE) -6-phenyl-hexa-2 , 4-dienoic acid, and by using . ( tetrahydrofuran-3-yl ) -methylamine instead of ( tetrahydrofuran-2-yl ) -methylamine .

t 0107]

The present compound (9) :

¹ H-NMR (CDC1 ₃ , TMS) 5(ppm) : 7.21(1H, d) , 6.61-6.69 ( 3.Η·, brs), 6.09(2H, m) , 5.77(1H, m) , 5.75(1H, brs), 3.87(1H, td) , 3.8K1H, dd), 3.74(1H,. dd) , 3.55(1H, dd) , 3.36(2H, m) , 2.58-2.62 (2H, t) , 2.16(2H, q) , 2.04(1H, m) , 1.72-1.77 ( 2H, m) , 1.62-1.65 (2H, m)

[ 0108]

Production Example 10

(2£, AE) -N- (Tetrahydrofuran-3-ylmethyl) -8- (2-thienyl ) - octa-2 , 4-dienamide represented by the following formula:

(hereinafter referred to as ' 'the present compound (10) ' ') was prepared in a manner similar to Production Example 1 by using ( 2E, E) -8- ( 2-thienyl ) -octa-2 , -dienoic acid instead of {2E, AE) -6-phenyl-hexa-2 , 4-dienoic acid, and by using (tetrahydrofuran-3-yl ) -methylamine instead of

(tetrahydrofuran-2-yl ) -methylamine . [ 0109]

The present compound (10) :

¹ H-NMR (CDCI3, TMS) 6(ppm) : 7.28 (1H, d) , 7.12 (1H, d) , 6.92(1H, t), 6.78 (lH; d) , 6.10(2H, m) , 5.77(1H, m) , 5.73(1H, brs), 3.89(1H,, td) , 3.81(1H, dd) , 3.74(1H, dd) , 3.55(1H, dd), 3.35-3.38 (2H, m) , 2.68-2.84 (2H, t) , 2.16(2H, ^' q) , 2.02(1H, m) , 1.79-1.83 (2H, m) , 1.62-1.65 (2H, m)

[ 0110]

Production Example 11

[2E, E) -N- (Tetrahydrofuran-3-ylmethyl) -6- (3, 4- dihydrobenzopyran-2-yl ) -hexa-2 , 4-dienamide represented by the following formula:

(hereinafter referred to as ' 'the present compound (11) ' ') was prepared in a manner similar to Production Example 1 by using ( 2E, 4E) -6- ( 3 , 4-dihydrobenzopyran-2-yl ) -hexa-2 , 4 - dienoic acid instead of (2E, 4E) -6-phenyl-hexa-2 , 4-dienoic acid, and by using ( tetrahydrofuran-3-yl ) -methylamine instead of (tetrahydrofuran-2-yl ) -methylamine .

[ 0111]

The present compound (11) :

¹ H-NMR (CDCI3, TMS) _. 5(ppm) : 7.28(1H, d) , 7 ,03-7.08 (2H, m) , 6.80(2H, m) , 6.24(2H, m) , 5.79(1H, d) , 5.73(1H, brs), 4.06(1H, m) , 3.88(1H, td) , 3.81(1H, . dd) ., 3.74(1H, dd) , 3.55(1H, dd) , 3.36(2H, m) , 2.52-2.77 ( 2H, t) , 2.44(2H, m) , 2.02-2.08 (1H, m) , 1.74-1.77 (2H, m) , 1.61-1.64 (2H, m)

[ 0112]

Production Example 12

[2E, 4£) -N- (Tetrahydrofuran-3-ylmethyl) -6- (indan-2-yl) - hexa-2 , 4-dienamide represented by the following formula:

(hereinafter referred to as ^{1 1} the present compound (12) ' ') was prepared in a manner similar to Production Example. 1 by using (2E, 42?) -6- (indan-2-yl) -hexa-2, 4-dienoic acid instead of {2E, 4£) -6-phenyl-hexa-2 , 4-dienoic acid, and by ( tetrahydrofuran-3-yl ) -methylamine using instead of ( tetrahydrofuran-2-yl ) -methylamine .

[ 0113]

The present compound (12) :

¹ H-NMR (CDCI3, TMS) δ (ppm) : 7.28 (1H, d) , 7.16-7.20 ( 4H, brs), 6.14(2H, m) , 5.77(1H, m) , 5.73(1H, brs), 3.89(1H, td) , 3.8M1H, dd) , 3.74(1H, dd) , 3.55(1H, dd) , 3.35-3.38 ( 2H, m) , 3.03(2H, dd) , 2.60-2.64 ( 3H, m) , 2.34(1H, t), 2.05(1H, m) , 1.74-1.77 (2H, m)

[ 0114]

Production Example 13 _. (2E, AE) -N- (Tetrahydrofuran-2-ylmethyl ) -6-(l, 2,3,4- tetrahydronaphthalen-2-yl) -hexa-2, 4-dienamide represented by the following formula:

(hereinafter referred to as ' 'the present compound (13) ' ') was prepared in a manner similar to Production Example 1 by using (2E, AE) -6- (1,2,3, 4-tetrahydronaphthalen-2-yl) -hexa- 2,4-dienoic acid instead of (2E, AE) -6-phenyl-hexa-2 , 4- dienoic acid.

[ 0115]

The present compound (13) :

¹ H-NMR (CDCI3, TMS) 5(ppm) : 7.28 (1H, d) , 7.04-7.10 ( 4H, m) , 6.18(2H, m) , 5.83(1H, d) , 5.77(1H, brs), 4.00(1H, m) , 3.88(1H, td) , 3.85(1H, dd) , 3.74(1H, dd) , 3,23(1H, m) , 2.72(2H, t), 2.46(2H, m) , 2.17(2H, m) , 1.87-2.00 ( 5H, m) , 1.56-1.64 (2H, m)

[ 0116]

Production Example 14

(2E, AE) -N- ( tetrahydrofuran-2-ylmethyl ) -8- (2-quinolyl) - octa-2 , 4-dienamide represented by the following formula: (hereinafter referred to as ' ' the present compound (14) ' ') was prepared in a manner similar to Production Example 1 by using {2E, 4£) -8- (2-quinolyl ) -octa-2 , 4-dienoic acid instead of {2E, 4E) -6-phenyl-hexa-2 , 4-dienoic acid.

[ 0117]

The present compound (14) :

¹ H-NMR (CDC1 ₃ , TMS) 5(ppm) : 8.07 (2H, m) , 7.78 (1H, d) , 7.69(1H, t), 7.57(1H, t), 7.40(1H, m), 7.20(1H, t), ^' β.14(2Η, m) , 5.77(1H, brs) , 5.73(1H, d) , 3.98(1H, td) , 3.85(1H, dd) , 3.74(1H, dd), 3.65(1H, dd) , 3.22(2H, m) , 3.01(2H, dd) , 2.34(1H, t), 1.87-2.05 (4H, m) , 1.76(2H, m)

[ 0118]

Production Example 15

(2E, E) ^' -N- (Tetrahydrofuran-3-ylmethyl) -8- ( 2-naphthyl ) - octa-2 , 4-dienamide represented by the following formula:

(hereinafter referred to as ' 'the present compound (15) ' ') was prepared in a manner similar to Production Example 1 by using [2E, E) -8- (2-naphthyl) -octa-2, 4-dienoic acid instead of {2E, 4E) -6-phenyl-hexa-2, 4-dienoic acid, and by using (tetrahydrofuran-3-yl ) -methylamine instead of

( tetrahydrofuran-2-yl ) -methylamine . The present compound ( 15 ) :

¹ H-N R (CDCI ₃ , TMS) 5(ppm) : 7.79 (3H, dd) , 7.60 (1H, s) , 7.43(2H,. dt), 7.3K1H, dd). , 7.21(1H, dd) , 6.12(2H, t) , 5.73(2H, t), 3.88(1H, td) , 3.81(1H, dd) , 3.73(1H, dd) , 3.55(1H, dd), 3.35(2H, dd) , 2.78(2H, t), 2.51(1H, m) , 2.2 _. 2(2H, dd) , 2.04(1H, dd) , 1.80-1.88 ( 2H, m) , 1.60-1.67 ( 1H, m)

[ 0119]

Production Example 16

X2E, AE) -N- (Tetrahydrofuran-3-ylmethyl) -8- (2-pyridyl) - octa-2 , 4-dienamide represented by: the following formula:

(hereinafter referred to as ' 'the present compound (16) ' ') was prepared in a manner similar to Production Example 1 by using (2E, AE) -8- (2-pyridyl) -octa-2, 4-dienoic acid instead of {2E, E) -6-phenyl-hexa-2 , 4-dienoic acid, and by using

( tetrahydrofuran-3-yl ) -methylamine instead of

(tetrahydrofuran-2-yl ) -methylamine .

The present compound (16) :

¹ H-NMR (CDC1 ₃ , TMS) δ (ppm) : 8.52 (1H, dd) , 7.57-7.63 (1H, m) , 7.16(3H, m) , 6.07-6.18 (2H, m) , 5.78(1H, t), 3.70-3.90 ( 4H, m) , 3.55(1H, dd) , 3.33-3.37 ( 2H, m) , 2.80(2H, t), 2.37(2H, m) , 2.04(2H, m) , 1.84-1.91 (2H, m) , 1.63(1H, td)

[ 0120]

Production Example 17

{2E, 4£) -N- ( tetrahydrofuran-3-ylmethyl) -8- (4- methoxyphenyl ) -octa-2 , 4 -dienamide represented

followin formula:

(hereinafter referred to as ' 'the present compound (17) ' ') was prepared in a manner similar to Production Example 1 by using (2£,4£) -8- ( 4-methoxyphenyl ) -octa-2, 4-dienoic acid instead of [2E, E) -6-phenyl-hexa-2 , 4-dienoic acid, and by using ( tetrahydrofuran-3-yl ) -methylamine instead of

(tetrahydrofuran-2-yl ) -methylamine . The present compound (17) :

¹ H-NMR (CDC1 ₃ ,. TMS) δ (ppm) : 7.79(1H, dd) , 7.60(1H, dd) , 7.44(1H, dd) , 7.25(1H, dd) , 7.08(1H, d) , 6.83(1H, t), 6.09- 6.17(2H, m) , 5.74(1H, m) , 5.62(1H, brs), 3.89(1H, td) , 3.81(3H, s) , 3.73(1H, dd) , 3.55(1H, dd) , 3.36(2H, m) , 2.79(1H, t), 2.50-2.58 (2H, m) , 2.19(2H, dt), 2.00-2.09 ( 1H, m) , 1.85(1H, t), 1.73 (1H, q) , 1.61-1.67 (1H, m)

[ 0121]

Production Example 18 (2E, AE) -N- (Tetrahydrofuran-2-ylmethyl) -8- (2- benzofuranyl ) -octa-2 , 4-dienamide represented - following formula:

(hereinafter referred to as ' 'the present compound (18) ' ') was prepared in a manner similar to Production Example 1 by using (2£, AE) -8- ( 2-benzofuranyl ) -octa-2, 4-dienoic acid instead of (2E, E) - 6-phenyl-hexa-2 , 4-dienoic acid.

The present compound (18) :

¹ H-NMR (CDCI3, TMS) 5(ppm) : 7.47-7.49 ( 1H, m) , 7.41(1H, t), 7.15-7,23 (3H, m) , 6.38(1H, d) , 6.12(2H, m) , 5.78(2H, t), 3.99(1H, m) , 3.84-3.89 (1H, m) , 3.73-3.78 (1H, m) , 3..67(1H, dq) , 3.22(1H, m) , 2.78(2H, t) , 2.26(2H, q) , 1.85-2.03 ( 4H, m) , 1.52-1.60 (2H, m)

[ 0122]

Production Example 19

(2E, E) -N- (Tetrahydrofuran-3-ylmethyl ) -6-benzyloxy- hexa-2, 4-dienamide represented by the following formula:

(hereinafter referred to as ' 'the present compound (19) ' ') was prepared in a manner similar to Production Example 1 by using (2E, AE) -6-benzyloxy-hexa-2 , 4-dienoic acid instead of {2E, AE) -6-phenyl-hexa-2 , -dienoic acid, and by using ( tetrahydrofuran-3-yl ) -methylamine instead of

( tetrahydrofuran-2-yl ) -methylamine .

The present compound (19) :

¹ H-NMR (CDCI ₃ , TMS) 5(ppm) : 7.21-7.38 ( 5H, m) , 6.39(1H, t), 6.15(1H, td) , 5.84(1H, d) , 5.66(1H, s), 4.56(2H, t) , 4.12(2H, t), 3.89(1H, m) , 3.81(1H, dd) , 3.74(1H, dd) , 3.56(1H, dd), 3.37(2H, dt), 2.51(1H, dd) , 2.01-2.17 ( 1H, m) , 1.60-1.62 (2H, m)

[ 0123]

Production Example 20

[2E, AE) -N- (Tetrahydrofuran-2-ylmethyl) -7-phenylthio- he ta-2 , 4 -dienamide represented by the following formula:

(hereinafter referred to as ' 'the present compound (20) ¹ ') was prepared in a manner similar to Production Example 1 by using (2E _r AE) -7-phenylthio-hepta-2 , 4-dienoic acid instead of (2E, E) -6-phenyl-hexa-2 , 4-dienoic acid.

The present compound (20) : H-NMR (CDCI ₃ , TMS) δ(ρρπι) : 7.25 (5H, m) , 6.03-6.21 (2H, m) , 5.77-5.83 (1H, m) , 3.98(1H, m) , 3.83-3.89 ( 1H, m) , 3.75(1H, dd) , 3.67(1H, dq) , 3.18-3.25 ( 1H, m) , 2.99(2H, t), 2.48 (2H, q) , 1.86-2.05 (4H, m) , 1.56(2H, dd)

[ 0124]

Production Example 21

(2E, AE) -N- (Tetrahydrofuran-2-ylmethyl) - (2E, AE) -8, 8- dimethyl-8-phenyl-octa-2 , 4-dienamide represented by the following formula:

(hereinafter referred to as ^{1 1} the present compound (21) ' ') was prepared in a manner similar to Production Example 1 by using ( 2E, AE) -8 , 8-dimethyl-8-phenyl-octa-2 , 4-dienoic acid instead of (2£7, AE) -6-phenyl-hexa-2 , 4-dienoic acid.

The present compound (21) :

¹ H-NMR (CDCI3, TMS) 5(ppm) : 7.29-7.34 ( 5H, m) , 6.01 (2H, dt), 5.78(1H, s), 3.94-4.01 (1H, m) , 3.98(1H, dd) , 3.85 (1H,. dt), 3.75(1H, dd), 3.66(1H, dq) , 3.17-3.24 ( 1H, m) , 1.86-2.02 ( 5H, m) , 1.72(2H, dd) , 1.55(2H, t), 1.34(6H, s)

[ 0125]

Production Example 22

(2E,.4£) -N- (Tetrahydrofuran-2-ylmethyl) -3-methyl-8- (3, 4-dichlorophenyl ) -octa-2, -dienamide represented by the following formula:

(hereinafter referred to as ' 'the present compound (22) ' ') was prepared in a manner similar to Production Example 1 by using (2E, 4E) -3-methyl-8- (3, 4-dichlorophenyl) -octa-2, 4- dienoic acid instead of {2E, 4E) -6-phenyl-hexa-2 , 4-dienoic acid. The present compound (22) :

¹ H-NMR (CDC1 ₃ , TMS) δ (ppm) : 7.34 (1H, d) , 7.26(1H, t), 7.00(1H, dd) , 5.97-6.07 (2H, m) , 5.85(lH, . s), 5.61(1H, s), 3.98(1H, dd), 3.86(1H, dd) , 3.75(1H, dd) , 3.64(1H, dq) , 3.16-3.22 (1H, m) , 2.58(2H, t), 2.26(2H, d) , 2.26(3H, s), 2.17(2H, dd), 1.94(2H, m), 1.69-1.77 ( 2H, m)

[ 0126]

With reference to the production of intermediates used in a preparation of the present compound, Reference Production Examples are shown below. .

[ 0127]

Reference Production Example 1

Under nitrogen atmosphere, to a mixture of ( tetrahydrofuran-3-yl ) -methanol represented by the following formula.:

(25 g) and pyridine (125 mL) was added p-toluenesulfonyl chloride (56 g) under ice-cooling, and the mixture was stirred under ice-cooling for 4. hrs. Then, water was added to the reaction mixture, and the mixture . was extracted twice with tert-butyl methyl ether. The organic layer was washed with 1 mol/L hydrochloric acid followed by saturated brine. The organic layer was dried over anhydrous sodium sulfate, and then filtered. The filtrate was concentrated under reduced pressure to obtain a crude product (58 g) of tetrahydrofuran-3-ylmethyl p-toluenesulfonate represented by the following formula:

The crude product was used without further purification in Reference Production Example 2.

[ 0128]

Reference Production Example 2

To a mixture of tetrahydrofuran-3-ylmethyl p- toluenesulfonate (29 g) , potassium iodide (23 g) , and N,N- dimethylformamide (300 mL) was added phthalimide potassium salt (22 g) under nitrogen atmosphere, and the mixture was stirred at 80°C for 3 hrs. Then, the reaction mixture was cooled under ice-cooling. Water was added to the mixture, and the resulting mixture was stirred for 30 minutes. The reaction mixture was filtered to collect a solid. The solid was dried under reduced pressure to give 2-

(tetrahydrofuran-3-ylmethyl) -isoindole-1 , 3-dione (14 g) represented by the following formula:

¹ H-NMR (CDC1 ₃ , TMS) 5(ppm): 7.86 (2H, dd) , 7.73 (2H, dd) , 3.9.4 (1H, td), 3.85-3.67 (4H, m) , 3.61(1H, dd) , 2.79-2.68 (1H, m) , 2.06-1.97 (1H, m) , 1.77-1.68 ( 1H, m)

[ 0129]

Reference Production Example 3

To a mixture of 2- ( tetrahydrofuran-3-ylmethyl ) - isoindole-1 , 3-dione (14 g) and ethanol (150 mL) was added hydrazine monohydrate (4.6 g) under nitrogen atmosphere, and the mixture was stirred at 70°C for 6 hrs. Then, the mixture was allowed to cool to room temperature, and filtered, and the resultant residue was washed with ethanol To the resulting filtrate was added a suspension of Raney nickel (1 mL) , and the mixture was stirred at 60°C for 4 hrs. The reaction mixture was cooled to room temperature, and then filtered. To the filtrate was added 1 mol/L solution of hydrogen chloride in diethyl ether (90 mL) . The mixture was concentrated under reduced pressure to give a crude product (10 g) of ( tetrahydrofuran-3-yl ) - methylamine hydrochloride represented by the following formula:

The crude was used without further purification in the next step.

[ 0130]

Next, specific examples of the present compound shown below.

In the following specific examples, each symbol of

X1 X2 X3 X4 X5 X6

X7 X8 X9 X10 X1 1

t 0131]

Y1 Y4 Y5

Y6 Y7 Y8 Y9 Y10

[ 0132]

The compound represented by Formula (1-15):

wherein a combination of X and Y is selected from th combinations of X and Y shown in Tables 1 to 3.

[ 0133]

The compound represented by Formula (1-16]

wherein a combination of X and Y is selected from th combinations of X and Y shown in Tables 1 to 3.

[ 0134]

The compound represented by Formula (1-17) H H

( 1 - 1 7 )

H H wherein a combination of X and Y is selected from the combinations of X and Y shown in Tables 1 to 3.

[ 0135]

The compound represented by Formula (1-18) :

wherein a combination of X and Y is selected from the combinations of X and Y shown in Tables 1 to 3.

[ 0136]

The compound represented by Formula (1-19) : wherein a combination of X and Y is selected from the combinations of X and Y shown in Tables 1 to 3.

[ 0137]

The compound represented by Formula (1-20) : wherein a combination of X and Y is selected from combinations of X and Y shown in Tables 1 to 3.

[ 0138]

The compound represented by Formula (1-21) :

wherein a combination of X and Y is . selected from the combinations of X and Y shown in Tables 1 to 3.

[ 0139]

The compound represented by Formula (1-22):

wherein a combination of X and Y is selected from the combinations of X and Y shown in Tables 1 to 3.

[ 0140]

The compound represented by Formula (1-23) :

wherein a combination of X and Y is selected from the combinations of X and Y shown in Tables 1 to 3.

[ 0141]

The combinations of X and Y in the compounds. represented by the above Formula (1-15) to Formula (1-23) are shown below. In Tables 1 to 3, Combination No., the group represented by X, and the group represented by Y are shown in this order. [ 0142]

Table 1

[ 0143]

Table 2

Combination Combination

X Y X Y

No. No.

41 X5 Yl 61 X7 Yl

42 X5 Y2 62 X7 Y2

43 X5 Y3 63 X7 Y3

44 X5 Y4 64 X7 Y4

45 X5 Y5 65 X7 Y5

46 X5 Y6 66 X7 Y6

47 X5 Y7 67 X7 Y7 48 X5 Y8 68 X7 Y8

49 X5 Y9 69 X7 Y9

50 X5 Yl 0 70 X7 Yl 0

51 X6 Yl 71 X8 Yl

52 X6 Y2 72 X8 Y2

53 X6 Y3 73 X8 · Y3

54 X6 Y4 74 X8 Y4

55 X6 Y5 75 X8 Y5

56 X6 Y6 76 X8 Y6

57 X6 Y7 77 X8 Y7

58 X6 Y8 78 X8 Y8

59 X6 Y9 79 X8 Y9

60 X6 Yl 0 80 X8 Yl 0

[ 0144]

Table 3

[ 0145]

Formulation Examples are shown below. The term "part(s)" means part(s) by weight. Formulation Example 1

Twenty (20) parts of any one of the present compounds (1) to (22) is dissolved in 65 parts of xylene, and then 15 parts of SORPOL 3005X (registered trade name of TOHO Chemical Industry Co., Ltd.) is added thereto. The mixture is stirred well to obtain an emulsifiable concentrate.

[ 0146]

Formulation Example 2

Forty (40) parts of any one of the present compounds

(1) to (22) and 5 parts of SORPOL 3005X are well mixed, and then 32 parts of Carplex#80 (synthetic hydrous silicon oxide, registered trade name of Shionogi & Co., Ltd.), and 23 parts of 300-mesh diatomaceous earth are added thereto. The mixture is mixed well with , a blender to obtain a wettable powder.

[ 0147]

Formulation Example 3

One point, five (1.5) parts of any one of the present compounds (1) to (22), 1 part of Tokuseal GUN (synthetic hydrous silicon oxide, manufactured by Tokuyama corporation), 2 parts of Reax 85A (sodium ligninsulfonate, manufactured by West vaco chemicals), 30 parts of Bentonite Fu i (bentonite, manufactured by HOJUN), and 65.5 parts of Shokozan A clay (kaolin clay, manufactured by Shokozan Kogyosho) are well mixed while grinding, ^■ and water is. added thereto. The mixture is then kneaded well, granulated with an extrusion granulator, and dried to obtain a 1.5% granular formulation.

[ 0148]

Formulation Example 4

Ten ^' (10) parts of any one of the present compounds (1) to (22), 10 parts ^' of phenylxylylethane, and 0.5 part of Sumijule L-75 . (tolylene diisocyanate, manufactured by Sumitomo Bayer Urethane Co. Ltd.) are mixed, and then the mixture is added to 20 parts of 10% aqueous solution of arabic gum, followed by stirring the resulting mixture with a homomixer to obtain an emulsion having a mean particle diameter of 20 ym. 2 parts of ethylene glycol is added to the emulsion, and. the mixture is stirred in a warm bath at 60 ^D C for 24 hrs to obtain a microcapsule slurry. Separately, 0.2 part of xanthan gum, and 1.0 part of Veegum R (aluminum magnesium silicate, manufactured by Sanyo Chemical Industries, Ltd.) are dispersed in 56.3 parts of ion-exchanged water to obtain a thickening agent solution.

42.5 parts of the above microcapsule slurry and 57.5 parts of the above thickening agent solution are mixed to obtain a microcapsule formulation.

[ 0149]

Formulation Example 5 Ten (10) parts of any one of the present compounds (1) to (22) and 10 parts of phenylxylylethane are mixed, and the mixture is added to 20 parts of 10% aqueous solution of polyethylene glycol, followed by stirring the resulting mixture with a homomixer to obtain an emulsion having a mean particle diameter of 3 μπι. Separately, 0.2 part of xanthan gum, and 1.0 part of Veegum R (aluminum magnesium silicate, manufactured by. Sanyo Chemical Industries, Ltd.) are dispersed in 58.8 parts of ion-exchanged water to obtain a thickening agent solution. 40 parts of the above emulsion and 60 parts of the above thickening agent solution are .mixed to obtain a fl.owable formulation.

[ 0150]

Formulation Example 6

Five (5) parts of any one of the present compounds (1) to (22), 3 parts of Carplex#80 (a fine powder of synthetic hydrous silicon oxide, registered trade name of Shionogi & Co., Ltd.), 0.3 parts of PAP (a mixture of monoisopropyl phosphate and diisopropyl phosphate) and 91.7 parts of talc (300 mesh) are mixed with a blender to obtain a dust formulation.

[ 0151]

Formulation Example 7

Zero point one (0.1) part of any one of the present compounds (1) to (22) is dissolved in 10 parts of isopropyl alcohol, and the mixture is mixed with 89.9 parts of deodorized kerosene to obtain an oil solution.

[ 0152]

Formulation Example 8

One (1) part of any one of the present compounds (1) to (22), 5 parts of dichloromethane and 34 parts of deodorized kerosene are mixed so as to be dissolved. The resulting solution is put into an aerosol vessel, and then a valve is attached to the vessel. 60 parts of a propellant (liguefied petroleum gas) is filled under pressure into the vessel through the valve to obtain an oil-based aerosol.

[ 0153]

Formulation Example 9

Zero point six (0.6) part of any one of the present compounds (1) to (22), 5 parts of xylene, 3.4 parts of deodorized kerosene and 1 parts of ATMOS 300 (emulsifier, registered trade name of Atlas Chemical) are mixed so as to be dissolved, and the resulting solution and 50 parts of water are put into an aerosol vessel, and then a valve is attached to the vessel. 40 parts of a propellant

(liguefied petroleum gas) is filled under pressure into the vessel through the valve to obtain an agueous aerosol.

[ 0154]

Formulation Example 10 Zero point three (0.3) g of any one of the present compounds (1) to (22) is dissolved in 20 mL of acetone. The resulting solution is uniformly mixed with 99.7 g of a base material for an insecticidal coil (a mixture of Tabu- powder, Pyrethrum marc and wood powder in a ratio of 4:3:3) . To the mixture is added 100 mL of water, and the resulting mixture is kneaded well, then molded and dried to obtain an insecticidal coil.

[ 0155]

Formulation Example 11

Zero point eight. (0.8) g of any one of the present compounds (1) to (22) and 0.4 g of piperonyl butoxide are dissolved in acetone so as to give a total amount of 10 mL. A base material for an insecticidal mat for electric heating (a plate of compacted . fibrils of a mixture of cotton linter and pulp: 2.5 cm x 1.5 cm, 0.3 cm in thickness) is uniformly impregnated with 0.5 mL of the above solution to obtain an insecticidal mat for electric heating.

[ 0156]

Formulation Example 12

Three (3) parts of any one of the present compounds (1) to (22) is dissolved in 97 parts of deodorized kerosene to obtaine a solution. The solution is put in a container made of polyvinyl chloride. Into the container is inserted an absorptive wick which is prepared by solidifying powders of an inorganic substance with a binder followed by sintering them and whose upper portion can be heated by a heater, to obtain a part of an absorptive wick type electric heating vaporizer.

[ 0157]

Formulation Example 13

One hundred (100) mg of any one of the present compounds (1) to (22). is dissolved in an appropriate amount of acetone. A porous ceramic plate (4.0 cm x 4.0 cm, 1.2 cm in thickness) is impregnated with the solution to obtain a fumigant for heating.

[ 0158]

Formulation Example 14

One hundred (100) pg of any one of the present compounds (1) to (22) is dissolved into an appropriate amount of acetone. The solution is uniformly applied on a filter paper (2 cm x 2 cm, 0.3 mm in thickness) . Then the filter paper . is air-dried to remove acetone to obtain a formulation vaporizable at room temperature.

[ 0159]

Next, the control efficacy of the present compound on the harmful arthropods is shown in Test Examples.

[ 0160]

Test Example 1 Zero point five (0.5) part of any one of the present compounds (1) to (14), (18), (19), and (22) was dissolved in 10 parts of isopropyl alcohol, and the mixture is mixed with 89.5 parts of deodorized kerosene to obtain a test solution.

Ten (10) German cockroaches {Blattella germanica, 5 males and 5 females) . were released in a test container (diameter 8.75 cm, height 7.5 cm, the bottom face is made of 16 mesh metallic wire) , the inner face on which butter was applied, and the container was set at the bottom of a test chamber (bottom face: 46 cm ^χ 46 cm, height: 70 cm) .

From a height of 60 cm above the upper surface of the container, each 1.5 mL of the oil solutions (test solutions) of the present compound (1) to (14), (18), (19), and (22) was sprayed by using a spray gun at a spraying pressure of 0.42 kg/cm ² . Thirty (30) seconds after the spraying, the container was taken out of the test chamber. Five (5) minutes after the spraying, the number of knocked- down . insects was counted to calculate a knock-down ratio. The knock-down ratio was calculated by the following equation .

Knock-down ratio (%) = (Number of Knocked-down insects / Total number of Tested insects) x 100

. The results showed that the knock-down ratios of the insects treated with the present compounds (1) to (14), (18), (19), and (22) were 100 %.

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Test Example 2

Each of the formulations prepared according to Formulation example 7 by using the present compounds ( 1 ) , (2), (4) to (9), (11) to (15), (17), and (18) was diluted with a mixture (isopropyl alcohol / deodorized kerosene = 1 / 9) so that the concentration of the active ingredient was 0.02% w/v, to obtain a test solution.

Ten. (10) imagoes, of common house mosquitoes {Culex pipens pallens) were released in a polyethylene cup (diameter of the bottom: 10.6 cm), and the polyethylene cup was covered with 16-mesh nylon gauze. The cup was set at the bottom of a test chamber (bottom face: 46 cm ^χ 46 cm, height: 70 cm) .

From a height of 30 cm above the upper surface of the polyethylene cup, 0.5 mL of the test solution was sprayed by using a spray gun at a spraying pressure of 0.4 kg/cm ² ..

Promptly after the spraying, the cup was taken out of the container. Ten (10) minutes after the spraying, the number of knocked-down insects was counted to calculate a knock-down ratio. The knock-down ratio was calculated by the following equation.

Knock-down ratio (%) = (Number of Knocked-down insects/Total number of Tested insects) x 100 The results showed that the knock-down ratios of the insects treated with each of the present compounds (1), (2), (4) to (9), (11) to (15), (17), and (18) were 100%.

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The present compound has an excellent control efficacy on harmful arthropods, is therefore useful as an active ingredient of an agent for controlling harmful arthropods .