OHSHITA JUN (JP)
MATSUO NORITADA (JP)
OHSHITA JUN (JP)
| WO2010136221A1 | 2010-12-02 |
| JPS5775961A | 1982-05-12 | |||
| EP0317188A2 | 1989-05-24 | |||
| JPS5775961A | 1982-05-12 |
MICHAEL ELLIOT ET AL: "Synthesis and Insecticidal Activity of Lipophilic Amides. Part 5: Influence on Activity of Varying the Substituent on Nitrogen", PESTICIDE SCIENCE, vol. 18, no. 4, 1 January 1986 (1986-01-01), pages 229 - 238, XP055034272, ISSN: 0031-613X
PESTICIDE SCIENCE, vol. 18, 1987, pages 211 - 221
TETRAHEDRON LETTERS, vol. 26, no. 21, 1985, pages 2317 - 2520
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 113, 1991, pages 5066 - 5068
| CLAIMS 1. An amide com ound represented by the formula (I) : wherein, Y represents 3 to 7 membered saturated heterocyclic ring group containing at least one atom or group selected from the group consisting of an oxygen atom or -S(0)t- as ring components (hereby, said 3 to 7 membered saturated heterocyclic ring optionally having 1 to 3 atoms or groups selected from the group D described below) ; t represents 0, 1 or 2; X represents a C1-C7 chain hydrocarbon group optionally having one or more atoms or group selected from group A described below, besides a number of carbon atoms consisting most long linear carbon chain is not more than 5, or a hydrogen atom; W represents an oxygen atom or -S(0)u-; u represents 0, 1 or 2; r represents 0 or 1; R1, R2, R3 and R4 are same or differnt and represent a C1-C4 alkyl group optionally having one or more halogen atoms, a hydrogen atom or a halogen atom; R5 and R6 are same or differnt and represent a C1-C4 alkyl group optionally haying one or more halogen atoms, a hydrogen atom or a halogen atom; R7 and R8 are same or differnt and represent a C1-C4 alkyl group optionally having one or more halogen atoms or a hydrogen atom; and n represents 1 or 2; group D: a group consisting of a C1-C4 alkyl group optionally having one or more halogen atoms, a C1-C4 alkoxy group optionally having one or more halogen atoms and a halogen atom; group A: a group consisting of a C1-C4 alkoxy group optionally having one or more halogen atoms, a C1-C4 alkylthio group optionally having one or more halogen atoms, a C1-C4 alkylsulfinyl group optionally having one or more halogen atoms, a C1-C4 alkylsulfonyl group optionally having one or more halogen atoms or a halogen atom. 2. The amide compound according to claim 1, wherein Y is a group of formula (Il-a) or (Il-b) : wherein, Y1 represents an oxygen atom or a sulfur atom; D1 represents an atom or a group selected from the group D; m represents 0 or 1; p represents 0, 1 or 2; q represents 0 or 1. 3. The amide compound accoring to claim 2, wherein p is 1; and q is 0. 4. The amide compound according to claim 2, wherein p is 2; and q is 1. 5. The amide conpound according to any one of claims 2 to 4, wherein Y1 is an oxygen atom. 6. The amide compound accoding to claim 2, wherein Y is the group of formula (Il-a), and Y1 is an oxygen atom. 7. The amide conpound according to claim 2, wherein Y is the group of formula (Il-b) . 8. The amide compound according to any one of claims 1 to 7, wherein R1 is a hydrogen atom or a halogen atom; R2 is a C1-C4 alkyl group optionally having one or more halogen atoms or a hydrogen atom; both of R3, R4, R5, R6 and R7 are hydrogen atoms; and R8 is a C1-C4 alkyl group optionally having one or more halogen atoms or a hydrogen atom. 9. The amide compound according to any one of claims 1 to 8, wherein r is 0. 10. The amide compound according to any one of claims 1 to 9, wherein X is a C1-C4 alkyl group optionally having one or more atoms or groups selected from the group B described below, a C3-C4 alkenyl group optionally having one or more atoms or groups selected from the group B described below or a C3-C4 alkynyl group optionally having one or more atoms or groups selected from the group B described below, group B: a group consisting of C1-C4 alkoxy group optionally having one or more halegen atoms, a C1-C4 alkylthio group optionally having one or more halogen atoms or a halogen atom. 11. The amide compound according to any one of claims 1 to.9, wherein X is a C1-C4 alkyl group, a C3-C4 alkenyl group or a C3-C4 alkynyl group. 12. A harmaful arthropod control agent containing the amide compound according to claim 1 and an inert carrier. 13. A method for controlling harmaful arthropods which comprises a step of applying an effective amount of the amide compound according to claim 1 to harmful arthropods or habitats thereof. |
DIENE AMIDES AND THEIR USE AGAINST ARTHROPODS
Technical Field
[0001]
The present invention relates to an amide compound and a usage thereof.
Background Art
[0002]
Hitherto, various harmaful arthropod control agents are investigaged and used. Amide compounds were described in Patent Literature 1 and Non Patent Literature 1.
Citation List
Patent Literature
[0003]
Patent Literature 1: JP 57-75961 A
Non Patent Literature
[0004]
Non Patent Literature 1: Pesticide Science, 1987, 18, p. 211-221.
Summary of the Invention
Problems to be Solved by the Invention [0005]
An object of the present invention is to provide novel compound having excellent control effect on harmful
arthropods .
Means for Solving the Problems
[0006]
As a result of intensive research conducted by the present inventors in an attempt to find compounds having excellent control effect on harmful arthropods, it has been found that amide compound represented by the following formula (I) has an excellent control effect on harmful arthropods. Thus, the present invention has been
accomplished.
That is, the present invention provides:
1] An amide compound represented by the formula (I):
wherein,
Y represents 3 to 7 membered saturated heterocyclic ring group containing at least one atom or group selected from the group consisting of an oxygen atom or -S(0) t _ as ring components (hereby, said 3 to 7 membered saturated heterocyclic ring optionally having 1 to 3 atoms or groups , selected from the group D described below) ;
t represents 0, 1 or 2;
X represents a C1-C7 chain hydrocarbon group
optionally having one or more atoms or group selected from group A described below, besides a number of carbon atoms consisting most long linear carbon chain is not more than 5, or a hydrogen atom;
W represents an oxygen atom or -S(0) u -;
u represents 0, 1 or 2;
r represents 0 or 1;
R 1 , R 2 , R 3 and R 4 are same or differnt and represent a C1-C4 alkyl group optionally having one or more halogen atoms, a hydrogen atom or a halogen atom;
R 5 and R 6 are same or differnt and represent a C1-C4 alkyl group optionally having one or more halogen atoms, a hydrogen atom or a halogen atom;
R 7 and R 8 are same or differnt and represent a C1-C4 alkyl group optionally having one or more halogen atoms or a hydrogen atom; and
n represents 1 or 2;
group D:
a group consisting of a C1-C4 alkyl group optionally having one or more halogen atoms, a C1-C4 alkoxy group optionally having one or more halogen atoms and a halogen atom;
group A:
a group consisting of a C1-C4 alkoxy group optionally having one or more halogen atoms, a C1-C4 alkylthio group optionally having one or more halogen atoms, a C1-C4 alkylsulfinyl group optionally having one or more halogen atoms, a C1-C4 alkylsulfonyl group optionally having one or more halogen atoms or a halogen atom (hereinafter referred to as the present compound) .
[2] The amide compound according to [1], wherein Y is a roup of formula (Il-a) or (Il-b) :
wherein,
Y 1 represents an oxygen atom or a sulfur atom;
D 1 represents an atom or a group selected from the group D;
m represents 0 or 1;
p represents 0, 1 or 2;
q represents 0 or 1.
[3] The amide compound accoring to [2], wherein p is 1; and q is 0.
[4] The amide compound according to [2], wherein p is 2; and q is 1. [5] The amide conpound according to any one of [2] to [4], wherein Y 1 is an oxygen atom.
[6] The amide compound accoding to [2], wherein Y is the group of formula (Il-a) , and Y 1 is an oxygen atom.
[7] The amide conpound according to [2], wherein Ύ is the group of 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-C4 alkyl group optionally having one or more halogen atoms or a hydrogen atom; both of R 3 , R 4 , R 5 , R 6 and R 7 are hydrogen atoms; and R 8 is a C1-C4 alkyl group optionally having 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] The amide compound according to any one of [1] to [9], wherein X is a C1-C4 alkyl group optionally having one or more atoms or groups selected from the group B described below, a C3-C4 ' alkenyl group optionally having one or more atoms or groups selected from the group B described below or a C3-C4 alkynyl group optionally having one or more atoms or groups selected from the group B described below, group B:
a group consisting of C1-C4 alkoxy group optionally having one or more halegen atoms, a C1-C4 alkylthio group optionally having one or more halogen atoms or a halogen atom.
[11] The amide compound according to any one of [1] to [9], wherein X is a C1-C4 alkyl group, a C3-C4 alkenyl group or a C3-C4 alkynyl group.
[12] A harmaful arthropod control agent containing the amide compound according to any one of [1] to [11] and an inert carrier.
[13] A method for controlling harmaful arthropods which comprises a step of applying an effective amount of the amide compound according to any one of [1] to [11] to harmful arthropods or habitats thereof.
Effect of invention
[0007]
The present compound is useful as an active ingredient of a harmful arthropods control agent because the present compound has an excellent activity in controlling harmful arthropods. Description of Embodyment
[0008]
In some case, in the present compound, there are isomers derived from one or more asymmetric carbon atoms and isomers derived from double bonds. Each isomer having harmful arthropods control activity or a mixture of isomers in arbitrary ratio which has harmful arthropod control activity is included in the present invention.
Furthermore, in the present compound, "2-position of the carbonyl group" means the position of a carbon atom indicated with number of "2" and "4-position of the
carbonyl group" means the position of a carbon atom
indicated with number of "4" in formula (I) described below.
[0009]
In the present invention, examples of the 3 to 7 membered saturated heterocyclic group containing at least one atom or group selected from the group consisting of an oxygen atom or -S(0) t _ as a ring component (hereby, said 3 to 7 membered saturated heterocyclic ring optionally having 1 to 3 atoms or groups selected from the group D described above) includes as follows:
3 to 7 membered saturated heterocyclic group
containing one or more oxygen atoms as a ring component (hereby, said 3 to 7 membered saturated heterocyclic ring optionally having 1 to 3 atoms or groups selected from the group D described above) 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-2-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-2-yl group, a 1, 3-dioxan-4-yl group, a 1,3- dioxan-5-yl group, a 1, 4-dioxan-2-yl group, a oxepan-2-yl group, a oxepan-3-yl group, a oxepan-4-yl group, a 1,3- dioxepan-2-yl group, a 1 , 3-dioxepan-4-yl group, a 1,3- dioxepan-5-yl group, a 1 , 4-dioxepane-2-yl , a 1 , 4-dioxepane- 5-yl group and a 1 , 4-dioxepane-6-yl group;
3 to 7 membered saturated heterocyclic group
containing one or more sulfur atoms as a ring component (hereby, said 3 to 7 membered saturated heterocyclic ring optionally having 1 to 3 atoms or groups selected from the group D described above) 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-2-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-2-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-2-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 and a 1, 4-dithiepan-6-yl group;
3 to 7 membered saturated heterocyclic group
containing one or more -SO- groups as a ring component
(hereby, said 3 to 7 membered saturated heterocyclic ring optionally having 1 to 3 atoms or groups selected from the group D described above) such as a l-oxo-thietan-2-yl group, a l-oxo-thietan-3-yl group, a l-oxo-tetrahydrothiophen-2-yl group, a l-oxo-tetrahydrothiophen-3-yl group, a 1-oxo- tetrahydrothiopyran-2-yl group, a 1-oxo- tetrahydrothiopyran-3-yl group, a 1-oxo- tetrahydrothiopyran-4-yl group, a l-oxo-thiepan-2-yl group, a l-oxo-thiepan-3-yl group and l-oxo-thiepan-4-yl group;
3 to 7 membered saturated heterocyclic group
containing one or more -SO2- groups as a ring component (hereby, said 3 to 7 membered saturated heterocyclic ring optionally having 1 to 3 atoms or groups selected from the group D described above) such as a 1 , l-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 and 1,1-dioxo- thiepan-4-yl group; 3 to 7 membered saturated heterocyclic group
containing one or more oxygen atoms and one or more -S(0) t _ groups as ring components (hereby, said 3 to 7 membered saturated heterocyclic ring optionally having 1 to 3 atoms or groups selected from the group D described above) such as a 1 , 3-oxathietan-2-yl group, a 1 , 3-oxathiolan-2-yl group, a 1, 3-oxathiolan-4-yl group, a 1 , 3-oxathiolan-5-yl group, a 1, 3-oxathian-2-yl group, a 1 , 3-oxathian-4-yl group, a 1,3- oxathian-5-yl group, a 1 , 4-oxathian-2-yl group and 1,4- oxathan-3-yl group.
[0010]
In the present invention, examples of a halogen atom include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.
In the present invention, examples of a C1-C4 alkyl group optionally having one or more halogen atoms include a methyl group, an ethyl group, a propyl group, an iso-propyl 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 1,1,2,2,2- pentfluoroethyl group.
In the present invention, examples of a C1-C4 alkoxy group optionally having one or more halogen atoms include a methoxy group, an ethoxy group, a ' propoxy group, an iso- propoxy 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 1 , 1 , 2 , 2 , 2-pentafluoroethoxy group.
In the present invention, examples of a C1-C4
alkylthio group optionally having one or more halogen atoms include a methylthio group, an ethylthio group, a
propylthio group, an iso-propylthio 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 1, 1, 2, 2, 2-pentafluoroethylthio group.
. In the present invention, examples of a C1-C4
alkylsulfinyl group optionally having one or more halogen atoms include a methylsulfinyl group, an ethylsulfinyl group, a propylsulfinyl group, an iso-propylsulfinyl group, a butylsulfinyl group, a difluoromethylsulfinyl group, a trifluoromethylsulfinyl group, a trichloromethylsulfinyl group, a 2 , 2 , 2-trifluoroethylsulfinyl group, a 1,1,2,2- tetrafluoroethylsulfinyl group and 1,1,2,2,2- pentafluoroethylsulfinyl group.
In the present invention, examples of a C1-C4
alkylsulfonyl group optionally having one or more halogen atoms include a methylsulfonyl group, an ethylsulfonyl group, a propylsulfonyl group, an iso-propylsulfonyl group, a butylsulfonyl group, a difluoromethylsulfonyl group, a trifluoromethylsulfonyl group, a trichloromethylsulfonyl group, a 2 , 2 , 2-trifluoroethylsulfonyl group, a 1,1,2,2- tetrafluoroethylsulfonyl group and 1,1,2,2,2- pentafluoroethylsulfonyl group.
[0011]
In the present invention, examples of a C1-C7 chain hydrocarbon group optionally having one or more atoms or group selected from group A, besides a number of carbon atoms consisting most long linear carbon chain is not more than 5 include a methyl group, an ethyl group, an iso- propyl group, a tert-butyl group, a propyl group, a sec- butyl group, an iso-butyl group, a 1 , 1-dimethylpropyl group, a 2, 2-dimethylpropyl group, an 1-ethylpropyl group, a butyl group, a 1-methylbutyl group, a 2-methylbutyl group, a 3- methylbutyl group, a 1 , 1-dimethylbutyl group, a 2,2- dimethylbutyl group, a 3, 3-dimethylbutyl group, an 1-ethyl- butyl group, an 2-ethyl-butyl group, a pentyl group, 1- methylpentyl group, a 2-methylpentyl group, .a 3- methylpentyl group, a 4-methylpentyl group, a 1,1- dimethylpentyl group, a 2 , 2-dimethylpentyl group, a 3,3- dimethylpentyl group, a 4 , 4-dimethylpentyl group, an 1- ethylpentyl group, an 2-ethylpentyl group, an 3-ethylpentyl group,
a trifluoromethyl group, a 2 , 2 , 2-trifluoroethyl group, a 3, 3, 3-trifluoropropyl group, a 4 , 4 , 4-trifluorobutyl group, a 5 , 5 , 5-trifluoropentyl group, a methoxymethyl group, a 2- methoxyethyl group, a 3-methoxypropyl group, a 4- methoxybutyl group, a 5-methoxypentyl group, a trifluoromethoxymethyl group, a 2-trifluoromethoxyethyl group, a 3-trifluoromethoxypropyl group, a 4- trifluoromethoxybutyl group, a 5-trifluoromethoxypentyl group, a 2, 2, 2-trifluoroethoxymethyl group, a 2- (2,2,2- trifluoroethoxy) ethyl group, a 3- (2,2,2- trifluoroethoxy) propyl group, a 4- (2,2, 2- trifluoroethoxy) butyl group, a 5- (2,2, 2- trifluoroethoxy) pentyl group, a methylthiomethyl group, a 2-methylthioethyl group, a 3-methylthiopropyl group, a 4- methylthiobutyl group, a 5-methylthiopentyl group, a methylsulfinylmethyl group, a 2-methylsulfinylethyl group, a 3-methylsulfinylpropyl group, a 4-methylsulfinylbutyl group, a 5-methylsulfinylpentyl . group, a methylsulfonylmethyl group, a 2-methylsulfonylethyl group, a 3-methylsulfonylpropyl group, a 4-methylsulfonylbutyl group, a 5-methylsulfonylpentyl group;
In the present invention, examples of a C2-C7 alkenyl group optionally having one or more atoms or group selected from group A , besides a number of carbon atoms consisting most long linear carbon chain is not more than 5 include a 2-propenyl group, a l-methyl-2-propenyl group, a 1,1- dimethyl-2-propenyl group, a l-ethyl-2-propenyl group, a 3- butenyl group, a l-methyl-3-butenyl group, a 1 , 1-dimethyl- 3-butenyl group, an l-ethyl-3-butenyl group, a 4-pentenyl group, a l-methyl-4-pentenyl group, a 1, l-dimethyl-4- pentenyl group, an l-ethyl-4-pentenyl group, a 3,3- difluoro-2-propenyl group, a 3 , 3-difluoro-l-methyl-2- propenyl group, a 3 , 3-difluoro-1 , l-dimethyl-2-propenyl group, an l-ethyl-3 , 3-difluoro-2-propenyl group, a 4,4- difluoro-3-butenyl group, a 4 , 4-difluoro-l-methyl-3-butenyl group, a 4 , 4-difluoro-1 , l-dimethyl-3-butenyl group, a 1- ethyl-4 , 4-difluoro-3-butenyl group, a 5, 5-difluoro-4- pentenyl group, a 5 , 5-difluoro-l-methyl-4-pentenyl group, a 5, 5-difluoro-1, l-dimethyl-4-pentenyl group, an l-ethyl-5, 5- difluoro-4-pentenyl group, a 2-butenyl group, .a l-methyl-2- butenyl group, a 1, l-dimethyl-2-butenyl group, a l-ethyl-2- butenyl group, a 3-pentenyl group, a l-methyl-3-pentenyl group, a 1 , l-dimethyl-3-pentenyl group, an l-ethyl-3- pentenyl group, a 4-methoxy-2-butenyl group, a 4-methoxy-l- methyl-2-butenyl group, a 4-methoxy-l, l-dimethyl-2-butenyl group, an l-ethyl-4-methoxy-2-butenyl group, a
5-methoxy-3-pentenyl group, a 5-methoxy-l-methyl-3-pentenyl group, a 5-methoxy-l , l-dimethyl-3-pentenyl group, an 1- ethyl-5-methoxy-3-pentenyl group, a 4-methylthio-2-butenyl group, a 4-methylthio-l-methyl-2-butenyl group, 4- methylthio-1, l-dimethyl-2-butenyl group, an l-ethyl-4- methylthio-2-butenyl group, a 5-methylthio-3-pentenyl group, a 5-methylthio-l-methyl-3-pentenyl group, a 5-methylthio- 1, l-dimethyl-3-pentenyl group, an l-ethyl-5-methylthio-3- pentenyl group;
In the present invention, examples of a C2-C7 alkynyl group optionally having one or more atoms or group selected from group A , besides a number of carbon atoms consisting most long linear carbon chain is not more than 5 include a
2-propinyl group, a l-methyl-2-propynyl group, a 1,1- dimethyl-2-propynyl group, an l-ethyl-2-propynyl group, a
3-butynyl group, a l-methyl-3-butynyl group, a 1,1- dimethyl-3-butynyl group, an l-ethyl-3-butynyl group, a 4- pentynyl group, a l-methyl-4-pentynyl group, a 1,1- dimethyl-4-pentynyl group, an l-ethyl-4-pentynyl group, a 3-fluoro-2-propynyl · group, a 3-fluoro-l-methyl-2-propynyl group, a 3-fluoro-1 , l-dimethyl-2-propynyl group, an 1- ethyl-3-fluoro-2-propynyl group, a 4-fluoro-3-butynyl group, a 4-fluoro-l-methyl-3-butynyl group, a 4-fluoro-1 , 1- dimethyl-3-butynyl group, an l-ethyl-4-fluoro-3-butynyl group, a 5-fluoro-4-pentynyl group, a 5-fluoro-l-methyl-4- pentynyl group, a 5-fluoro-1, l-dimethyl-4-pentynyl group, l-ethyl-5-fluoro-4-pentynyl group, a 2-butynyl. group, a 1- methyl-2-butynyl group, a 1 , l-dimethyl-2-butynyl group, a l-ethyl-2-butynyl group, a 3-pentynyl group, a l-methyl-3- pentynyl group, a 1 , l-dimethyl-3-pentynyl group, an 1- ethyl-3-pentynyl group.
[0012]
Examples of the present compound include as follows: a compound represented by the formula (I), wherein relative configlation of R 1 and R 2 is a trans configlation;
a compound represented by the formula (I) rich in a
compopund, wherein relative configlation of R 1 and R 2 is a trans configlation;
a compound represented by the formula (I) containing not less than 80 % of which is a compound, wherein relative configlation of R 1 and R 2 is a trans configlation;
a compound represented by the formula (I) containing not less than 90 % of which is a compound, wherein relative configlation of R 1 and R 2 is a trans configlation;
a compound represented by the formula (I), wherein relative configlation of R 1 and R 2 is a trans configlation, and relative configlation of R 3 and R 4 is a trans configlation; a compound represented by the formula (I) rich in a
compound, wherein relative configlation of R 1 and R 2 is a trans configlation, and relative configlation of R 3 and R 4 is a trans configlation;
a compound represented by the formula (I) containing not less than 80 % of which is a compound, wherein relative configlation of R 1 and R 2 is a trans configlation, and relative configlation of R 3 and R 4 is a trans configlation; a compound represented by the formula (I) containing not. less than 90 % of -Which is a compound, wherein relative configlation of R 1 and R 2 is a trans configlation, and relative configlation of R 3 and R 4 is a trans configlation;
[0013]
a compound represented by the formula (I), wherein R 3 , R 4 , R 5 and R 6 are hydrogen atoms;
a compound represented by the formula (I), wherein R 3 , R 4 , R 5 , R 6 and R 7 are hydrogen atoms;
a compound represented by the formula (I), wherein R 3 , R 4 , R 5 , R 6 and R 7 are hydrogen atoms, and R 8 is a C1-C4 alkyl group optionally having one or more halogen atoms;
a compound represented by the formula (I), wherein R 3 , R 4 , R 5 , R 6 and R 7 are hydrogen atoms, and R 8 is a methyl group; a compound represented by the formula (I),, wherein R 3 , R 4 , R 5 and R 6 are hydrogen atoms, R 7 is a C1-C4 alkyl group optionally having one or more halogen atoms, and R 8 is a C1-C4 alkyl group optionally having one or more halogen atoms ;
a compound represented by the formula (I), wherein R 3 , R 4 , R 5 and R 6 are hydrogen atoms, R 7 is a methyl group, and R 8 is a methyl group;
[0014]
a compound represented by the formula (I) , wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 are hydrogen atoms; [0015]
a compound represented by the formula (I), wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 are hydrogen atoms, and R 8 is a C1-C4 alkyl group optionally having one or more halogen atoms; a compound represented by the formula (I) , wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 are hydrogen atoms, and R 8 is a methyl group;
[0016]
a compound represented by the formula (I), wherein R 1 , R 3 , R 4 , R 5 , R 6 and R 7 are hydrogen atoms, R 2 is a C1-C4 alkyl group optionally having one or more halogen atoms, and R 8 is a hydrogen atom;
a compound represented by the formula (I) , wherein R 1 , R 3 , R 4 , R 5 , - R 6 and R 7 are hydrogen atoms, R 2 is a C1-C4 alkyl group optionally having one or more halogen atoms, and R 8 is a C1-C4 alkyl group optionally having one or more halogen atoms;
a compound represented by the formula (I) , wherein R 1 , R 3 , R 4 , R 5 , R 6 and R 7 are hydrogen atoms, R 2 is a methyl group, and R 8 is a hydrogen atom;
a compound represented by the formula (I), wherein R 1 , R 3 , R 4 , R 5 , R 6 and R 7 are hydrogen atoms, R 2 is a methyl group, and R 8 is a methyl group;
[0017]
a compound represented by the formula (I), wherein R 3 , R 4 , R 5 , R 6 and R 7 are hydrogen atoms, R 1 is a halogen atom, R 2 is a C1-C4 alkyl group optionally having one or more halogen atoms, and R 8 is a hydrogen atom;
a compound represented by the formula (I), wherein R 3 , R 4 , R 5 , R 6 and R 7 are hydrogen atoms, R 1 is a halogen atom, R 2 is a C1-C4 alkyl group optionally having one or more halogen atoms, and R 8 is a C1-C4 alkyl group optionally having One or more halogen atoms;
a compound represented by the formula (I), wherein R 3 , R 4 , R 5 , R 6 and R 7 are hydrogen atoms, R 1 is a fluorine atom, R 2 is a methyl group, and R 8 is a hydrogen atom;
a compound represented by the formula (I) , wherein R 3 , R 4 , R 5 , R 6 and R 7 are hydrogen atoms, R 1 is a fluorine atom, R 2 is a methyl group, and R 8 is a methyl group;
[0018]
a compound represented by the formula (I) , wherein X is a C1-C4 chain hydrocarbon group ;
a compound represented by t'he formula (I), wherein X is a methyl ' group ;
a compound represented by the formula (I), wherein X is an ethyl group ;
a compound represented by the formula (I), wherein X is a propyl group ;
a compound represented by the formula (I), wherein X is a butyl group ; a compound represented by the formula (I), wherein X is a C2-C4 alkyl group ;
a compound represented by the formula (I), wherein X is a
2.2.2-trifluoroethyl group;
a compound represented by the formula (I) , wherein X is a
3.3.3-trifluoropropyl group;
a compound represented by the formula (I), wherein X is a
4.4.4-trifluorobutyl group;
a compound represented by the formula (I), wherein X is a 2-methoxyethyl group ;
a compound represented by the formula (I), wherein X is a
3-methoxypropyl group ;
a compound represented by the formula (I) , wherein X is a
4-methoxybutyl group ;
a compound represented by the formula (I), wherein X is a C2-C4 alkyl group optionally having one or more fluorine atoms or one or more methoxy groups ;
a compound represented by the formula (I), wherein X is a
2-propenyl group ;
a compound represented by the formula (I), wherein X is a
3-butenyl group ;
a compound represented by the formula (I), wherein X is a C3-C.4 alkenyl group ;
a compound represented by the formula (I), wherein X is a 3 , 3-difluoro-2-propenyl group; a compound represented by the formula (I) , wherein X is a 4 , 4-difluoro-3-butenyl group;
a compound represented by the formula (I), wherein X is a 4-methoxy-2-butenyl group ;
a compound represented by the formula (I), wherein X is a C3-C4 alkenyl group optionally having one or more fluorine atoms or one or more methoxy groups ;
a compound represented by the formula (I), wherein X is a
2-propynyl group ;
a compound represented by the formula (I), wherein X is a
3-butynyl group ;
a compound represented by the formula (I), wherein X is a C3-C4 alkynyl group ;
[0019]
a compound represented by the formula (I), wherein Y is 4 to 6 membered saturated heterocyclic ring group containing one or two oxygen atom(s) as ring components;
a compound represented by the formula (I), wherein Y is 4 to 6 membered saturated heterocyclic ring group containing an oxygen atom as a a ring component;
a compound represented by the formula (I), wherein Y is 4 to 6 membered saturated heterocyclic ring group containing two oxygen atoms as ring components;
a compound represented by the formula (I) , wherein Y is 4 to 6 membered saturated heterocyclic ring group containing an oxygen atom or one -S(0) t - as ring components;
a compound represented by the formula (I), wherein Y is 4 to 6 membered saturated heterocyclic ring group containing an oxygen atom or one -S(0) t - as ring components, and t is 0;
[0020]
a compound represented by the formula (I), wherein Y is a group of said formula (Il-a); that is a compound
represented by formula (1-1) :
wherein, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , X, W, r, n, Y 1 , D 1 , m and p are the same meanings as defined above;
a compound represented by the formula (1-1), wherein D 1 is a methyl group or an ethyl group;
a compound represented by the formula (1-1), wherein D 1 is a methyl group or an ethyl group, and n is 1;
a compound represented by the formula (1-1), wherein D 1 is a methyl group or an ethyl group, n is 1, R 1 , R 3 , R 4 , R 5 , R 6 and R 7 are hydrogen atoms, R 2 is a hydrogen atom or a methyl group and R 8 is a hydrogen atom or a methyl group; that is a compound represented by the formula (1-1-1) :
wherein, R 2_1 represents a hydrogen atom or a methyl group, R 8"1 represents a hydrogen atom or a methyl group, D 1_1 represents a methyl group or an ethyl group, X, W, r, Y 1 , m and p are the same meanings as defined above;
a compound represented by the formula (1-1-1), wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-1-1) rich in a compound, wherein a relative configulation of the double - bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-1-1) containing not less than 80 % of which is a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-1-1) containing not less than 90 % of which is a compound, wherein a.
relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-1-1), wherein r is 0, X is a C2-C4 alkyl group optionally having one or more atoms or groups selected from a group consisting of a halogen atom, a methoxy group, and a methylthio group, or a C3-C4 alkenyl group optionally having one or more atoms or groups selected from a group consisting of a halogen atom, a methoxy group, and a methylthio group; that is a compound represented by the formula (1-1-2):
wherein, X 1"2 represents a C2-C4 alkyl group optionally having one or more atoms or groups selected from a group consisting of a halogen atom, a methoxy group, and a methylthio group, or a C3-C4 alkenyl group optionally having one or more atoms or groups selected from a group consisting of a halogen atom, a methoxy group, and a methylthio group, and R 2"1 , R 8"1 , D 1"1 , Y 1 , m and p are the same meanings as defined above;
a compound represented by the formula (1-1-2), wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation; a compound represented by the formula (1-1-2) rich in a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (i-1-2) containing not less than 80 % of which is a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-1-2) containing not less than 90 % of which is a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-1-1), wherein r is 1, W is an oxygen atom, X is a C2-C4 alkyl group optionally having one or more atoms or groups selected from a group consisting of a halogen atom, a methoxy group, and a methylthio group, or a C3-C4 alkenyl group optionally having one or more atoms or groups selected from a group consisting of a halogen atom, a methoxy group, and a methylthio group; that is a compound represented by the formula (1-1-3) :
wherein, X 1"2 , R 2"1 , R 8"1 , D 1"1 , Y 1 , m and p are the same meanings as defined above;
a compound represented by the formula (1-1-3) , wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-1-3) rich in a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-1-3) containing not less than 80 % of which is a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-1-3) containing not less than 90 % of which is a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
[0021] a compound represented by the formula (1-1), wherein Y 1 is an oxygen atom;
a compound represented by the formula (1-1) , wherein Y 1 is an oxygen atom and D 1 is a methyl group or an ethyl group; a compound represented by the formula (1-1), wherein Y 1 is an oxygen atom, D 1 is a methyl group or an ethyl group, and n is 1;
a compound represented by the formula (1-1), wherein Y 1 is an oxygen atom, D 1 is a methyl group or an ethyl group, n is 1, R 1 , R 3 , R 4 , R 5 , R 6 and R 7 are hydrogen atoms, R 2 is a hydrogen atom or a methyl group and R 8 is a hydrogen atom or a methyl group; that is a compound represented by the formula (1-2-1) :
wherein, R 2"1 , R 8"1 , D 1_1 , X, W, r, m and p are the same meanings as defined above;
a. compound represented by the formula (1-2-1) , wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-2-1) rich in a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-2-1) containing not less than 80 % of which is a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-2-1) containing not less than 90 % of which is a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-2-1), wherein r is 0, X is a C2-C4 alkyl group optionally having one or more atoms or groups selected from a group consisting of a halogen atom, a methoxy group, and a methylthio group, or a C3-C4 alkenyl group optionally having one or more atoms or groups selected from a group consisting of a halogen atom, a methoxy group, and a methylthio group; that is a compound represented by the formula (1-2-2) :
as defined above;
a compound represented by the formula (1-2-2), wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-2-2) rich in a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-2-2) containing not less than 80 % of which is a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the . formula (1-2-2) containing not less than 90 % of which is a compound, wherein a' relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-2-1), wherein r is 1, is an oxygen atom, X is a C2-C4 alkyl group optionally having one or more atoms or groups selected from a group consisting of a halogen atom, a methoxy group, and a methylthio group, or a C3-C4 alkenyl group optionally having one or more atoms or groups selected from a group consisting of a halogen atom, a methoxy group, and a methylthio group; that is a compound represented by the formula ( 1-2-3 ) :
wherein, X 1-2 , R 2_1 , R 8"1 , D 1"1 , m and p are the same meanings as defined above;
a compound represented by the formula (1-2-3), wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-2-3) rich in a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-2-3) containing not less than 80 % of which is a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-2-3) containing not less than 90 % of which is a compound, wherein, a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
[0022]
a compound represented by formula (I), wherein Y is an oxetanyl group optionally having an atom or a group
selected from the group D;
a compound represented by the formula (I), wherein Y is an oxetanyl group optionally having a methyl group or an ethyl group;
a compound represented by the formula (I), wherein Y is an oxetanyl group optionally having a methyl group or an ethyl group, and n is 1;
a compound represented by the formula (I), wherein Y is an oxetanyl group optionally having a methyl group or an ethyl group, n is 1, R 1 , R 3 , R 4 , R 5 , R 6 and R 7 are hydrogen atoms, R 2 is a hydrogen atom or a methyl group, and R 8 is a hydrogen atom or a methyl group; that is a compound
represented by the formula (1-3-1) :
wherein, Y 3 is an oxetan group optionally having a methyl group or an ethyl group, R 2"1 , R 8"1 , X, W and r are the same meanings as defined above; a compound represented by the formula (1-3-1), wherein a relative configulation of the double bond presented on the 2-position and 3-position of the ' carbonyl group is a E configlation;
a compound represented by the formula (1-3-1) rich in a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-3-1) containing not less than 80 % of which is a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-3-1) containing not less than 90 % of which is a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-3-1), wherein r is 0, X is a C2-C4 alkyl group optionally having one or more atoms or groups selected from a group consisting of a halogen atom, a methoxy group, and a methylthio group, or a C3-C4 alkenyl group optionally having one or more atoms or groups selected from a group consisting of a halogen atom, a methoxy group, and a methylthio group; that is a compound represented by the formula (1-3-2):
wherein, Y 3 , X 1"2 , R 2-1 and R 8"1 are the same meanings as defined above;
a compound represented by the formula (1-3-2), wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-3-2) rich in a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-3-2) containing not less than 80 % of which is a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-3-2) containing not less than 90 % of which is a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation; a compound represented by the formula (1-3-1), wherein r is
1, is an oxygen atom, X is a C2-C4 alkyl group optionally having one or more atoms or groups selected from a group consisting of a halogen atom, a methoxy group, and a methylthio group, or a C3-C4 alkenyl group optionally having one or more atoms or groups selected from a group consisting of a halogen atom, a methoxy group, and a methylthio group; that is a compound represented by the formula ( 1-3-3 ) :
wherein, Y 3 , X 1-2 , R 2"1 and R 8-1 are the same meanings as defined above;
a compound represented by the formula (1-3-3), wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-3-3) rich in a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-3-3) containing not less than 80 % of which is a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-3-3) containing not less than 90 % of which is a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
[0023]
a compound represented by formula (I), wherein Y is an oxetan-3-yl group optionally having an atom or a group selected from the group D at the 3-position of oxetane ring;
a compound represented by formula (I), wherein Y is an oxetan-3-yl group optionally having a methyl group or an ethyl group at the 3-position of the oxetane ring;
a compound represented by formula (I), wherein Y is an oxetan-3-yl group optionally having a methyl group or an ethyl group at the 3-position of the oxetane ring, and ' n is 1;
a compound represented by formula (I), wherein Y is an oxetan-3-yl group optionally having a methyl group or an ethyl group at the 3-position of the oxetane ring, n is 1, R 1 , R 3 , R 4 , R 5 , R 6 and R 7 are hydrogen atoms, R 2 is a
hydrogen atom or a methyl group, and R 8 is a hydrogen atom or a methyl group; that is a compound represented by the formula ( 1-4-1 ) :
wherein, Y is an oxetan-3-yl group optionally having a methyl group or an ethyl group at the 3-position of the oxetane ring, R 2"1 , R 8_1 , X, W and r are the same meanings as defined above;
a compound represented by the formula (1-4—1), wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a.E configlation;
a compound represented by the formula (1-4-1) rich in a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-4-1) containing not less than 80 % of which is a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-4-1) containing not less than 90 % of which is a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-4-1), wherein r is 0, X is a.C2-C4 alkyl group optionally having one or more atoms or groups selected from a group consisting of a halogen atom, a methoxy group, and a methylthio group, or a C3-C4 alkenyl group optionally having one or more atoms or groups selected from a group consisting of a. halogen atom, a methoxy group, and a methylthio group; that is a compound represented by the formula (1-4-2):
wherein, Y 4 , X 1"2 , R 2-1 and R 8-1 are the same meanings as defined above;
a compound represented by the formula (1-4-2), wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-4-2) rich in a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation; a compound represented by the formula (1-4-2) containing not less than 80 % of which is a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-4-2) containing not less than 90 % of which is a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-4-1), wherein r is 1, is an oxygen atom, X is a C2-C4 alkyl group optionally having one or more atoms or groups selected from a group consisting of a halogen atom, a methoxy group, and a methylthio group, or a C3-C4 alkenyl group optionally having one or more atoms or groups selected from a group consisting of a halogen atom, a methoxy group, and a methylthio group; that is a compound represented by the formula (1-4-3) :
wherein, Y 4 , X 1 2 , R 2 1 and R 8 1 are the same meanings as defined above; a compound represented by the formula (1-4-3), wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-4-3) rich in a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-4-3) containing not less than 80 % of which is a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-4-3) containing not less than 90 % of which is a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
[0024]
a compound represented by formula (I), wherein Y is a tetrahydrofuranyl group optionally having an atom or a group selected from the group D;
a compound represented by formula (I), wherein Y is a tetrahydrofuranyl group optionally having a methyl group or an ethyl group; a compound represented by formula (I), wherein Y is a tetrahydrofuranyl group optionally having a methyl group or an ethyl group, and n is 1;
a compound represented by the formula (I), wherein Y is a- tetrahydrofuranyl group optionally having a methyl group or an ethyl group, n is 1, R 1 , R 3 , R 4 , R 5 , R 6 and R 7 are
hydrogen atoms, R 2 is a hydrogen atom or a methyl group, and R 8 is a hydrogen atom or a methyl group; that is a compound represented by the formula (1-5-1):
wherein, Y 5 is a tetrahydrofuranyl group optionally having a methyl group or an ethyl group, R 2-1 , R 8"1 , X, W and r are the same meanings as defined above;
a compound represented by the formula (1-5-1), wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-5-1) rich in a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-5-1) containing not less than 80 % of which is a compound, wherein a relative configulation of the double bond, presented ' on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-5-1) containing not less than 90 % of which is a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-5-1), wherein r is 0, X is a C2-C4 alkyl group optionally having one or more atoms or groups selected from a group consisting of a halogen atom, a methoxy group, and a methylthio group, or a C3-C4 alkenyl group optionally having one or more atoms or groups selected from a group consisting of a halogen atom, a methoxy group, and a methylthio group; that is a compound represented by the formula (1-5-2) :
wherein, Y 5 , X 1"2 , R 2"1 and R 8"1 are the same meanings as defined above;
a compound represented by the formula (1-5-2), wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-5-2) rich in a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-5-2) containing not less than 80 % of which is a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-5-2) containing not less than 90 % of which is a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-5-1) , wherein r is 1, W is an oxygen atom, X is a C2-C4 alkyl group optionally having one or more atoms or groups selected from a group consisting of a halogen atom, a methoxy group, and a methylthio group, or a C3-C4 alkenyl group optionally having one or more atoms or groups selected from a group consisting of a halogen atom, a methoxy group, and a methylthio group; that is a compound represented by the formula (1-5-3) :
wherein, Y 5 , X 1-2 , R 2-1 and . R 8"1 are the same meanings as defined above;
a compound represented by the formula (1-5-3), wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-5-3) rich in a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-5-3) containing not less, than 80 % of which is a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-5-3) containing not less than 90 % of which is a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
[0025] a compound represented by formula (I), wherein Y is a tetrahydrofuran-2-yl group optionally having an atom or a group selected from the group D at the 2-position of tetrahydrofuran ring;
a compound represented by formula (I) , wherein Y is a tetrahydrof ran-2-yl group optionally having a methyl group or an ethyl group at the 2-position of the tetrahydrofuran ring;
a compound represented by formula (I), wherein Y, is a tetrahydrofuran-2-yl group optionally having a methyl group or an ethyl group at the 2-position of the tetrahydrofuran ring, and n is 1;
a compound represented by formula (I), wherein Y is a tetrahydrofuran-2-yl group optionally having a methyl " group or an ethyl group at the 2-position of the tetrahydrofuran ring, n is 1, R 1 , R 3 , R 4 , R 5 , R 6 and R 7 are hydrogen atoms, R 2 is a hydrogen atom or a methyl group, and R 8 is a hydrogen atom or a methyl group; that is a compound
represented by the formula (1-6-1):
wherein, Y 6 is a tetrahydrofuran-2-yl group optionally having a methyl group or an ethyl group at the 2-position of the tetrahydrofuran ring, R 2"1 , R 8-1 , X, W and r are the same meanings as defined above;
a compound represented by the formula (1-6-1), wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-6-1) rich in a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-6-1) containing not less than 80 % of which is a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-6—1) containing not less than 90 % of which is a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-6-1), wherein r is 0, X is a C2-C4 alkyl group optionally having, one or more atoms or groups selected from a group consisting of a halogen atom, a methoxy group, and a methylthio group, or a C3-C4 alkenyl group optionally having one or more atoms or groups selected from a group consisting of a halogen atom, a methoxy group, and a methylthio group; that is a compound represented by the formula (1-6-2):
wherein, Y 6 , X 1"2 , R 2"1 and R 8"1 are the same meanings as defined above;
a compound represented by the formula (1-6-2), wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-6-2) rich in a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-6-2) containing not less than 80 % of which is a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-6-2) containing not less than 90 % of which is a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-6-1) , wherein r is 1, W is an oxygen atom, X is a C2-C4 alkyl group optionally having one or more atoms or groups selected from a group consisting of a halogen atom, a methoxy group, and a methylthio group, or a C3-C4 alkenyl group optionally having one or more atoms or groups selected from a group consisting of a halogen atom, a methoxy group, and a methylthio group; that is a compound represented by the formula ( 1-6-3 ) :
wherein, Y 6 , X 1-2 , R 2"1 and R 8-1 are the same meanings as defined above;
a compound represented by the formula (1-6-3), wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the . formula (1-6-3) rich in. a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation; a compound represented by the formula (1-6-3) containing not less than 80 % of which is a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-6-3) containing not less than 90 % of which is a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
[0026]
a compound represented by formula (I), wherein Y is a tetrahydrofuran-3-yl group optionally having an atom or a group selected from the group D at the 3-position of the tetrahydrofuran ring;
a compound represented by formula (I), wherein Y is a tetrahydrofuran-3-yl group optionally having a methyl group or an ethyl group at the 3-position of the tetrahydrofuran ring;
a compound represented by formula (I), wherein Y is a tetrahydrofuran-3-yl group optionally having a methyl group or an . ethyl group at the 3-position of the tetrahydrofuran ring, and n is 1;
a compound represented by formula (I), wherein Y is a tetrahydrofuran-3-yl group optionally having a methyl group or an ethyl group at the 3-position of the tetrahydrofuran ring, n is 1, R 1 , R 3 , R 4 , R 5 , R 6 and R 7 are hydrogen atoms, R 2 is a hydrogen atom or a methyl group, and R 8 is a hydrogen atom or a methyl group; that is a compound represented by the formula (1-7-1):
wherein, Y is a tetrahydrofuran-3-yl group optionally having a methyl group or an ethyl group at the 3^position of the tetrahydrofuran ring, R 2-1 , R 8-1 , X, W and r are the same meanings as defined above;
a compound represented by the formula (1-7-1), wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-7-1) rich in a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-7-1) containing not less than 80 % of which is a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-7-1) containing not less than 90 % of which is a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-7-1), wherein r is 0, X is a C2-C4 alkyl group optionally having one or more atoms or groups selected from a group consisting of a halogen atom, a methoxy group, and a methylthio group, or a C3-C4 alkenyl group optionally having one or more atoms or groups selected from a group consisting of a halogen atom, a methoxy group, and a methylthio group; that is a compound represented by the formula (1-7-2) :
wherein, Y 7 , X 1"2 , R 2"1 and R 8_1 are the same meanings as defined above;
a compound represented by the formula (1-7-2), wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-7-2) rich in a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-7-2) containing not less than 80 % of which is a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-7-2) containing not less than 90 % of which is a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-7-1), wherein r is 1, W is an oxygen atom, X is a C2-C4 alkyl group optionally having one or more atoms or groups selected from. a group consisting of a halogen atom, a methoxy group, and a methylthio group, or a C3-C4 alkenyl group optionally having one or more atoms or groups selected from a group consisting of a halogen atom, a methoxy group, and a methylthio group; that is a compound represented by the formula (1-7-3) :
wherein, Y 7 , X 1-2 , R 2"1 and R 8"1 are the same meanings as defined above;
a compound represented by the formula (1-7-3), wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-7-3) rich in a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-7-3) containing not less than 80 % of which is a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-7-3) containing not less than 9.0 % of which is a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
[0027] a compound represented by formula (I), wherein Y is a tetrahydropyranyl group optionally having an atom or a group selected from the group D;
a compound represented by formula (I), wherein Y is a tetrahydropyranyl group optionally having a methyl group or an ethyl group;
a compound represented by formula (I), wherein Y is a tetrahydropyranyl group optionally having a methyl group or an ethyl group, and n is 1;
a compound represented by the formula (I), wherein Y is a tetrahydropyranyl group optionally having a methyl group or an ethyl group, n is 1, R 1 , R 3 , R 4 , R 5 , R 6 and R 7 are
hydrogen atoms, R 2 is a hydrogen atom or a methyl group, and R 8 is a hydrogen atom or a methyl group; that is a compound represented by the formula (1-8-1):
wherein, Y is a tetrahydropyranyl group optionally having a methyl group or an ethyl group, R 2"1 , R 8"1 , X, W and r are the same meanings as defined above;
a compound represented by the formula (1-8-1), wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-8-1) rich in a compound, wherein a relative configulation of the double, bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-8-1) containing not less than 80 % of which is a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-8-1) containing not less than 90 % of which is a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-8-1), wherein r is 0, X is a C2-C4 alkyl group optionally having one or more atoms or groups selected from a group consisting of a halogen atom, a methoxy group, and a methylthio group, or a C3-C4 alkenyl group optionally having one or more atoms or groups selected from a group consisting of a halogen atom, a methoxy group, and a methylthio group; that is a compound represented by the formula (1-8-2) :
wherein, Y 8 , X 1""2 , R 2"1 and R 8"1 are the same meanings as defined above;
a compound represented by the formula (1-8-2) , wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-8-2) rich in a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-8-2) containing not less than 80 % of which is a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-8-2) containing not less than 90 % of which is a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-8-1), wherein r is 1, W is an oxygen atom, X is a C2-C4 alkyl group optionally having one or more atoms or groups selected from a group consisting of a halogen atom, a methoxy group, and a methylthio group, or a C3-C4 alkenyl group optionally having one or more atoms or groups selected from a group consisting of a halogen atom, a methoxy group, and a methylthio group; that is a compound represented by the formula ( 1-8-3) :
wherein, Y 8 , X 1"2 , R 2"1 and R 8"1 are the same meanings as defined above;
a compound represented by the formula (1-8-3), wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-8-3) rich in a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-8-3) containing not less than 80 % of which is a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-8-3) containing not less than 90 % of which is a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
[0028]
a compound represented by formula (I), wherein Y is a tetrahydropyran-2-yl group optionally having an atom or a group selected from the group D at the 2-position of tetrahydropyran ring;
a compound represented by formula (I), wherein Y is a tetrahydropyran-2-yl group optionally having a methyl group or an ethyl group at the 2-position of the tetrahydropyran ring;
a compound represented by formula (I),, wherein Y is a tetrahydropyran-2-yl group optionally having a methyl group or an ethyl group at the 2-position of the tetrahydropyran ring, and n is 1;
a compound represented by formula (I), wherein Y is a tetrahydropyran-2-yl group optionally having a methyl group or an ethyl group, at the 2-position of the tetrahydropyran ring, n is 1, R 1 , R 3 , R 4 , R 5 , R 6 and R 7 are hydrogen atoms, R 2 is a hydrogen atom or a methyl group, and R 8 is a hydrogen atom or a methyl group; that is a compound represented by the formula (1-9-1) :
wherein, Y 9 is a tetrahydropyran-2-yl group optionally having a methyl group or an ethyl group at the 2-position of the tetrahydropyran ring, R 2-1 , R 8"1 , X, W and r are the same meanings as defined above;
a compound represented by the formula (1-9-1), wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-9-1) rich in a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-9-1) containing not less than 80 % of which is a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-9-1) containing not less than 90 % of which is a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-9-1), wherein r is 0, X is a C2-C4 alkyl group optionally having one or more atoms or groups selected from a group consisting of a halogen atom, a methoxy group, and a methylthio group, or a C3-C4 alkenyl group optionally having one or more atoms or groups selected from a group consisting of a halogen atom, a methoxy group, and a methylthio group; that is a compound represented by the formula (1-9-2):
wherein, Y 9 , X 1-2 , R 2-1 and R 8-1 are the same meanings as defined above;
a compound represented by the formula (1-9-2), wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-9-2) rich in a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation; a compound represented by the formula (1-9-2) containing not less than 80 % of which is a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-9-2) containing not less than 90 % of which is a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-9-1), wherein r is 1, W is an oxygen atom, X is a C2-C4 alkyl group optionally having one or more atoms or groups selected from a group consisting of a halogen atom, a methoxy group, and a methylthio group, or a C3-C4 alkenyl group optionally having one or more atoms or groups selected from a group consisting of a halogen atom, a methoxy group, and a methylthio group; that is a compound represented by the formula (1-9-3) :
wherein, Y 9 , X 1-2 R' 2-1 and R' 8-1 are the same meanings as defined above; a compound represented by the formula (1-9-3), wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-9-3) rich in a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-9-3) containing not less than 80 % of which is a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-9-3) containing not less than 90 % of which is a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E . -, configlation;
[0029]
a compound represented by formula (I), wherein Y is a tetrahydropyran-3-yl group optionally having an atom or a group selected from the group D at the 3-position of tetrahydropyran ring;
a compound represented by formula (I), wherein Y is a tetrahydropyran-3-yl group optionally having a methyl group or an ethyl group at the 3-position of the tetrahydropyran ring;
a compound represented by formula (I), wherein Y is a tetrahydropyran-3-yl group optionally having a methyl group or an ethyl group at the 3-position of the tetrahydropyran ring, and n is 1;
a compound represented by formula (I), wherein Y is a tetrahydropyran-3-yl group optionally having a methyl group or an ethyl group at the 3-position of the tetrahydropyran ring, n is 1, R 1 , R 3 , R 4 , R 5 , R 6 and R 7 are hydrogen atoms, R 2 is a hydrogen atom or a methyl group, and R 8 is a hydrogen atom or a methyl group; that is a compound
represented by the formula (1-10-1):
wherein, Y 10 is a tetrahydropyran-3-yl group optionally having a methyl group or an ethyl group at the 3-position of the tetrahydropyran ring, R 2"1 , R 8"1 , X, W and r are the same meanings as defined above;
a compound represented by the formula (1-10-1), wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation; a compound represented by the formula- (1-10-1) rich in a compound, wherein a. relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation
a compound represented by the formula. (1-10-1) containing not less than 80 % of which is a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-10-1) containing not less than 90 % of which is a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-10-1), wherein r is 0, X is a C2-C4 alkyl group optionally having one or more atoms or groups selected from a group consisting of a halogen atom, a methoxy group, and a methylthio group, or a C3-C4 alkenyl group optionally having one or more atoms or groups selected from a group consisting of a halogen atom, a methoxy group, and a methylthio group; that is a compound represented by the formula (1-10-2) :
wherein, Y 10 , X 1-2 , R 2"1 and R 8"1 are the same meanings as defined above;
a compound represented by the formula (1-10-2), wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-10-2) rich in acompound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-10-2) containing not less than 80 % of which is a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-10-2) containing not less than 90 % of which is a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-10-1), wherein r is 1, W is an oxygen atom, X is a C2-C4 alkyl group
optionally having one or more atoms or groups selected from a group consisting of a halogen atom, a methoxy group, and a methylthio group, or a C3-C4 alkenyl group optionally having one or more atoms or groups selected from a group consisting of a halogen atom, a methoxy group, and a methylthio group; that is a compound represented by the formula (1-10-3) :
wherein, Y 10 , X 1"2 , R 2"1 and R 8-1 are the same meanings ' as defined above;
a compound represented by the formula (1-10-3), wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-10-3) rich in a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-10-3) containing not less than 80 % of which is a compound, wherein a.
relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-10-3) containing not less than 90 % of which is a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
[0030]
a compound represented by formula (I), wherein Y is a tetrahydropyran-4-yl group optionally having an atom or a group selected from the group D at the 4-position of the tetrahydropyran ring;.
a compound represented by formula (I), wherein Y is a tetrahydropyran-4-yl group optionally having a methyl group or an ethyl group at the 4-position of the tetrahydropyran ring;
a compound represented by formula (I), wherein Y is a tetrahydropyran-4-yl group optionally having a methyl group or an ethyl group at the 4-position of the tetrahydropyran ring, and n is 1;
a compound represented by formula (I), wherein Y is a tetrahydropyran-4-yl group optionally having a methyl group or an ethyl group at the 4-position of the tetrahydropyran ring, n is 1, R 1 , R 3 , R 4 , R 5 , R 6 and R 7 are hydrogen atoms, R 2 is a hydrogen atom or a methyl group, and R 8 is a hydrogen atom or a methyl group; that is a compound represented by the formula (1-11-1):
wherein, Y 11 is a tetrahydropyran-4-yl group optionally having a methyl group or an ethyl group at the 4-position of the tetrahydropyran ring, R 2"1 , R 8-1 , X, W and r are the same meanings as defined above;
a compound represented by the formula (1-11-1), wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-11-1) rich in a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-11-1) containing not less than 80 % of which is a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-11-1·) containing not less than 90 % of which is a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-11-1), wherein r is 0, X is a C2-C4 alkyl group optionally having one or more atoms or groups selected from a group consisting of a halogen atom, a methoxy group, and a methylthio group, or a C3-C4 alkenyl group optionally having one or more atoms or groups selected from a group consisting of a halogen atom, a methoxy group, and a methylthio group; that is a compound represented by the formula (1-11-2):
wherein, Y 11 , X 1-2 , R 2_1 and R 8"1 are the same meanings as defined above;
a compound represented, by the formula (1-11-2), wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the - formula (1-11-2) rich in a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation; a compound represented by the formula (1-11-2) containing not less than 80 % of which is a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-11-2) containing not less than 90 % of which is a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-11-1), wherein r is 1, W is an oxygen atom, X is a C2-C4 alkyl group
optionally having one or more atoms or groups selected from a group consisting of a halogen atom, a methoxy group, and a methylthio group, or a C3-C4 alkenyl group optionally having one or more atoms or groups selected from a group consisting of a halogen atom, a methoxy group, and a methylthio group; that is a compound represented by the formula (1-11-3) :
wherein, Y 11 , X 1 2 , R 2 1 and R 8 1 are the same meanings as defined above; a compound represented by the formula (1-11-3), wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-11-3) rich in a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation; ·
a compound represented by the formula (1-11-3) containing not less than 80 % of which is a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-11-3) containing not less than 90 % of which is a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
[0031]
a compound represented by formula (I), wherein Y is a 1,3- dioxolanyl group optionally having an atom or a group selected from the group D or a 1,3-dioxanyl group
optionally having an atom or a group selected from the group D;
a compound represented by formula (I), wherein Y is a 1,3- dioxolanyl group optionally having a methyl group or an ethyl group or a 1,3-dioxanyl group optionally having a methyl group or an ethyl group;
a compound represented by formula (I), wherein Y is a 1,3 dioxolanyl group optionally having a methyl group or an ethyl group or a 1,3-dioxanyl group optionally having a methyl group or an ethyl group, and n is 1;
a compound represented by formula (I), wherein Y is a 1,3 dioxolanyl group optionally having a methyl group or an ethyl group or a 1,3-dioxanyl group optionally having a methyl group or an ethyl group, and n is 1, R 1 , R 3 , R 4 , R 5 , R 6 and R 7 are hydrogen atoms, R 2 is a hydrogen atom or a methyl group, and R 8 is a hydrogen atom or a methyl group, that is a compound represented by the formula (1-12-1) :
wherein, Y 12 is a 1 , 3-dioxolanyl group optionally having a methyl group or an ethyl group or a 1,3-dioxanyl group optionally having a methyl group or an ethyl group, R 2_1 , R 8_1 , X, W and r are the same meanings as defined above; a compound represented by the formula (1-12-1), wherein a relative configulation of the double- bond presented on th 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-12-1) rich in a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-12-1) containing not less than 80 % of which is a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-12-1) containing not less than 90 % of which is a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-12-1), wherein r is 0, X is a C2-C4 alkyl group optionally having one or more atoms or groups selected from a group consisting of a halogen atom, - a methoxy group, and a- methylthio group, or a C3-C4 alkenyl group optionally having one or more atoms or groups selected from a group consisting of a halogen atom, a methoxy group, and a methylthio group; that is a compound represented by the formula (1-12-2) :
wherein, Y 12 , X 1-2 , R 2-1 and R 8-1 are the same meanings as defined above;
a compound represented by the formula (1-12-2), wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-12-2) rich in a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-12-2) containing not less than 80 % of which is a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-12^2) containing not less than 90 % of which is a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-12-1), wherein r is 1, W is an oxygen atom, X is a C2-C4 alkyl group
optionally having one or more atoms or groups selected from a group consisting of a halogen atom, a methoxy group, and a methylthio group, or a C3-C4 alkenyl group optionally having one or more atoms or groups selected from a group consisting of a halogen atom, a methoxy group, and a methylthio group; that is a compound represented by the formula (1-12-3) :
wherein, Y 12 , X 1"2 , R 2"1 and R 8"1 are the same meanings as defined above;
a compound represented by the formula (1-12-3), wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-12-3) rich in a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-12-3) containing not less than 80 % of which is a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-12-3) containing not less than 90 % of which is a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
[0032]
a compound represented by formula (I), wherein Y is a 1,3- dioxolanyl group optionally having an atom or a group selected from the group D;
a compound represented by formula (I), wherein Y is a 1,3- dioxolanyl group optionally having a methyl group or an ethyl group;
a compound represented by formula (I), wherein Y is a 1,3- dioxolanyl group optionally having a methyl group or an ethyl group, and n is 1;
a compound represented by formula (I), wherein Y is a 1,3- dioxolanyl group optionally having a methyl group or an ethyl group, and n is 1, R 1 , R 3 , R 4 , R 5 , R 6 and R 7 are hydrogen atoms, R 2 is a hydrogen atom or a methyl group, and R 8 is a hydrogen atom or a methyl group; that is a compound represented by the formula (1-13-1):
wherein, Y is a 1 , 3-dioxolanyl group optionally having a methyl group or an ethyl group, R 2-1 , R 8"1 , X, W and r ' are the same meanings as defined above;
a compound represented by the formula (1-13-1), wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-13-1) rich in a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-13-1) containing not less than 80 % of which is a compound, wherein a relative configulation of the. double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the. formula (1-13-1) containing not less than 90 % of which is a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation; a compound represented by the formula (1-13-1), wherein r is 0, X is a C2-C4 alkyl group optionally having one or more atoms or groups selected from a group consisting of a> halogen atom, a methoxy group, and a methylthio group, or a C3-C4 alkenyl group optionally having one or more atoms or groups selected from a group consisting of a halogen atom, a methoxy group, and a methylthio group; that is a compound represented by the formula (1-13-2):
wherein, Y 13 , X 1-2 , R 2-1 and R 8-1 are the same meanings as defined above;
a compound represented by the formula (1-13-2), wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-13-2) rich in a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-13-2) containing not less than 80 % of which is a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-13-2) containing not less than 90 % of which is a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-13-1), wherein r is 1, W is an oxygen atom, X is a C2-C4 alkyl group
optionally having one or more atoms or groups selected from a group consisting of a halogen atom, a methoxy group, and a methylthio group, or a C3-C4 alkenyl group optionally having one or more atoms or groups selected from a group consisting of a halogen atom, a methoxy group, and a methylthio group; that is a compound represented by the formula (1-13-3):
wherein, Y 13 , X 1"2 , R 2-1 and R 8-1 are the same meanings as defined above;
a compound represented by the formula (1-13-3), wherein relative configulation of the double bond presented on 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-13-3) rich in a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-13-3) containing not less than 80 % of which is a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-13-3) containing not less than 90 % of which is a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
[0033]
a compound represented by formula (I), wherein Y is a 1,3- dioxan-5-yl group ■ optionally having an atom or a group selected from the group D at the 5-position of the 1,3- dioxane ring;
a compound represented by formula (I), wherein Y is a 1,3- dioxan-5-yl group optionally having a methyl group or an ethyl group at the 5-position of the 1,3-dioxane ring; a compound represented by formula (I), wherein Y is a 1,3- dioxan-5-yl group optionally having a methyl group or an ethyl group at the 5-position of the 1,3-dioxane ring, and n is 1;
a compound represented by formula (I), wherein Y is a 1,3- dioxan-5-yl group optionally having a methyl group or an ethyl group at the 5-position of the 1,3-dioxane ring, and n is 1, R 1 , R 3 , R 4 , R 5 , R 6 and R 7 are hydrogen atoms, R 2 is a hydrogen atom or a methyl group, and R 8 is a hydrogen atom or a methyl group; that is a compound represented by the formula (1-14-1) :
wherein, Y 14 is a 1 , 3-dioxan-5-yl group optionally having a methyl group or an ethyl group at the 5-position of the 1,3-dioxane ring, R 2"1 , R 8"1 , X, W and r are the same meanings as defined above;
a compound represented by the formula (1-14-1), wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-14-1) rich in a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation; a compound represented by the formula (1-14-1) containing not less than 80 % of which is a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-14-1) containing not less than 90 % of which is a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-14-1), wherein r is 0, X is a C2-C4 alkyl group optionally having one or more atoms or groups selected from a group consisting of a halogen atom, a methoxy group, and a methylthio group, or a C3-C4 alkenyl group optionally having one or more atoms or groups selected from a group consisting of a halogen atom, a methoxy group, and a methylthio group; that is a compound represented by the formula (1-14-2):
wherein, Y 14 , X 1"2 , R 2_1 and R 8-1 are the same meanings as defined above;
a compound represented by the formula (1-14-2) , wherein relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-14-2) rich in a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-14-2) containing not less than 80 % of which is a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-14-2) containing not less than 90 % of which is a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-14-1) , wherein r is 1, W is an oxygen atom, X is a C2-C4 alkyl group
optionally having one or more atoms or groups selected from a group consisting of a halogen atom, a methoxy group, and a methylthio group, or a C3-C4 alkenyl group optionally having one or more atoms or groups selected from, a group consisting of a halogen atom, a methoxy group, and a methylthio group; that is a compound represented by the formula (1-14-3) :
wherein, Y 14 , X 1"2 , R 2"1 and R 8"1 are the same meanings as defined above;
a compound represented by the formula (1-14-3), wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-14-3) rich in a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-14-3) containing not less than 80.% of which is a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-14-3) containing not less than 90 % of which is a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation; [0034]
a compound represented by formula (I), wherein Y is a 1,3- dioxan-2-yl group optionally having an atom or a group selected from the group D at the 2-position of the 1,3- dioxane ring;
a compound represented by formula (I), wherein Y is a 1,3- dioxan-2-yl group optionally having a methyl group or an ethyl group at the 2-position of the 1,3-dioxane ring;
a compound represented by formula (I), wherein Y is a 1,3- dioxan-2-yl group optionally having a methyl group or an ethyl group at the 2-position of the 1,3-dioxane ring, and n is 1 ;
a compound represented by formula (I), wherein Y is a 1,3- dioxan-2-yl group optionally having a methyl group or an ethyl group at the 2-position of the 1,3-dioxane ring, and n is 1, R 1 , R 3 , R 4 , R 5 , R 6 and R 7 are hydrogen atoms, R 2 is a hydrogen atom or a methyl group, and R 8 is a hydrogen atom or a methyl group; that is a compound represented by the formula (1-15-1) :
wherein, Y 15 is a 1 , 3-dioxan-2-yl group optionally having a methyl group or an ethyl group at the 2-position of the 1,3-dioxane ring, R 2-1 , R 8-1 , X, W and r are the same meanings as defined above;
a compound represented by the formula (1-15-1), wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a- E configlation;
a compound represented by the formula (1-15-1) rich in a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-15-1) containing not less than 80 % of which is a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-15-1) containing not less than 90 % of which is a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-15-1), wherein r is 0, X is a C2-C4 alkyl group optionally having one or more atoms or groups selected from a group consisting of a halogen atom, a methoxy group, and a methylthio group, or a C3-C4 alkenyl group optionally having one or more atoms or groups selected from a group consisting of a halogen atom, a methoxy group, and a methylthio group; that is a compound represented by the formula (1-15-2):
wherein, Y 15 , X 1-2 , R 2"1 and R 8"1 are the same meanings as defined above;
a compound represented by the formula (1-15-2), wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-15-2) rich in a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-15-2) containing not less than 80 % of which is a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-15-2) containing not less than 90 % of which is a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl . group is a E configlation; a compound represented by the formula (1-15-1), wherein r is 1, W is an oxygen atom, X is a C2-C4 alkyl group
optionally having one or more atoms or groups selected from a group consisting of a halogen atom, a methoxy group, and a methylthio group, or a C3-C4 alkenyl group optionally having one or more atoms or groups selected from a group consisting of a halogen atom, a methoxy group, and a methylthio group; that is a compound represented by the formula (1-15-3) :
wherein, Y 15 , X 1"2 , R 2-1 and R 8-1 are the same meanings as defined above;
a compound represented by the formula (1-15-3), wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-15-3) rich in a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-15-3) containing not less than 80 % of which is a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-15-3) containing not less than 90 % of which is a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
[0035]
a compound represented by formula (I), wherein Y is a 1,3- - dioxan-4-yl group optionally having an atom or a group selected from the group D at the 4-position of the 1,3- dioxane ring;
a compound represented by formula (I), wherein Y is a 1,3- dioxan-4-yl group optionally having a methyl group or an ethyl group at the 4-position of the 1,3-dioxane ring; a compound represented by formula (I), wherein Y is a 1,3- dioxan-4-yl group optionally having a methyl group or an ethyl group at the 4-position of the 1,3-dioxane ring, and n is 1;
a compound represented by formula (I), wherein Y is a 1,3- dioxan-4-yl group optionally having a methyl group or an ethyl group at the 4-position of the 1,3-dioxane ring, and n is 1, R 1 , R 3 , R 4 , R 5 , R 6 and R 7 are hydrogen atoms, R 2 is a hydrogen atom or a methyl group, and R 8 is a hydrogen atom or a methyl group; that is a compound represented by the formula (1-16-1) :
wherein, Y 16 is a 1 , 3-dioxan-4-yl group optionally having a methyl group or an ethyl group at the 4-position of the 1,3-dioxane ring, R 2"1 , R 8"1 , X, and r are the same meanings as defined above;
a compound represented by the formula (1-16-1), wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-16-1) rich in a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-16-1) containing not less than 80 % of which is a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-16-1) containing not less than 90 % of which is a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-16-1), wherein r is 0, X is a C2-C4 alkyl group optionally having one or more atoms or groups selected from a group consisting of a halogen atom, a methoxy group, and a methylthio group, or a C3-C4 alkenyl group optionally having one or more atoms or groups selected from a group consisting of a halogen atom, a methoxy group, and a methylthio group; that is a compound represented by the formula (1-16-2):
wherein, Y 16 , X 1"2 , R 2"1 and R 8"1 are the same meanings, as defined above;
a compound represented by the formula (1-16-2), wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-16-2) rich in a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-16-2) containing not less than 80 % of which is a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-16-2) containing not less than 90 % of which is a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-16-1), wherein r is 1, W is an oxygen atom, X is a C2-C4 alkyl group
optionally having one or more atoms or groups selected from a group consisting of a halogen atom, a methoxy group, and a methylthio group, or a C3-C4 alkenyl group optionally having one or more atoms or groups selected from a group consisting of a halogen atom, a methoxy group, and a methylthio group; that is a compound represented by the formula (1-16-3) :
wherein, Y 16 , X 1"2 , R 2-1 and R 8"1 are the same meanings as defined above;
a compound represented by the formula (1-16-3), wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-16-3) rich in a - compound, wherein a relative configulation of the double bond presented on the 2-position and , 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-16-3) containing not less than 80 % of which is a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-16-3) containing not less than 90 % of which is a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
[0036] a compound represented by formula (I), wherein Y is a 1,3- dioxolan-2-yl group optionally having an atom or a group selected from the group D at the 2-position of the 1,3- dioxolane ring;
a compound represented by formula (I), wherein Y is a 1,3- dioxolan-2-yl group optionally having a methyl group or an ethyl group at the 2-position of the 1 , 3-dioxolane ring; a compound represented by formula (I), wherein Y is a 1,3- dioxolan-2-yl group optionally having a methyl group or an ethyl group at the 2-position of the 1 , 3-dioxolane ring, and n is 1;
a compound represented by formula (I), wherein Y is a 1,3- dioxolan-2-yl group optionally ' having a methyl group or an ethyl group at the 2-position of the 1 , 3-dioxolane ring, and n is 1, R 1 , R 3 , R 4 , R 5 , R 6 and R 7 are hydrogen atoms, R 2 is a hydrogen atom or a methyl group, and R 8 is a hydrogen atom or a methyl group; that is a compound represented by the formula (1-17-1) :
wherein, Y is a 1 , 3-dioxolan-2-yl group optionally having a methyl group or an ethyl group at the 2-position of the 1, 3-dioxolane ring, R 2-1 , R 8"1 , X, W and r are the same meanings as defined above;
a compound represented by the formula (1-17-1), wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-17-1) rich in a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-17-1) containing not less than 80 % of which is a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-17-1) containing not less than 90 % of which is a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-17-1), wherein r is 0, X is a C2-C4 alkyl group optionally having one or more atoms or groups selected from a group consisting of a halogen atom, a methoxy group, and a methylthio group, or a C3-C4 alkenyl group optionally having one or more atoms or groups selected from a group consisting of a halogen atom, a methoxy group, and a methylthio group; that is a compound represented by the formula (1-17-2):
wherein, Y 17 , X 1"2 , R 2"1 and R 8"1 are the same meanings as defined above;
a compound represented by the formula (1-17-2), wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-17-2) rich in a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-17-2) containing not less than 80 % of which is a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-17-2) containing not less than 90 % of which is a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-17-1), wherein r is 1, W is an oxygen atom, X is a C2-C4 alkyl group
optionally having one or more atoms or groups selected from a group consisting of a halogen atom, a me ' thoxy group, and a methylthio group, or a C3-C4 alkenyl group optionally having one or more atoms or groups selected from a group consisting of a halogen atom, a methoxy group, and a methylthio group; that is a compound represented by the formula (1-17-3) :
wherein, Y 17 , X 1"2 , R 2"1 and R 8"1 are the same meanings as defined above;
a compound represented by the formula (1-17-3), wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-17-3) rich in a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-17-3) containing not less than 80 % of which is a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-17-3) containing not less than 90 % of which is a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
[0037]
a compound represented by formula (I), wherein Y is a 1,3- dioxolan-4-yl group optionally having an atom or a group selected from the group D at the 4-position of the 1,3- dioxolane ring;
a compound represented by formula (I), wherein Ϋ is a 1,3- dioxolan-4-yl group optionally having a methyl group or an ethyl group at the 4-position of the 1 , 3-dioxolane ring; a compound represented by formula (I), wherein Y is a 1,3- dioxolan-4-yl group optionally having a methyl group or an ethyl group at the 4-position of the 1 , 3-dioxolane ring, and n is 1;
a compound represented by formula (I), wherein Y is a 1,3- dioxolan-4-yl group optionally having a methyl group or an ethyl group at the 4-position of the 1 , 3-dioxolane ring, and n is 1, R 1 , R 3 , R 4 , R 5 , R 6 and R 7 are hydrogen atoms, R 2 is a hydrogen atom or a methyl group, and R is a hydrogen atom or a methyl group; that is a compound represented by the formula (1-18-1) :
wherein, Y 18 is a 1, 3-dioxolan-4-yl group optionally having a methyl group or an ethyl group at the 4-position of the 1 , 3-dioxolane ring, R 2_1 , R 8-1 , X, W and r are the same meanings as defined above;
a compound represented by the formula (1-18-1), wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-18-1) rich in a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-18-1) containing not less than 80 % of which is a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-18-1) containing not less than 90 % of which is a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-18-1), wherein r is 0, X is a C2-C4 alkyl group optionally having one or more atoms or groups selected from a group consisting of a halogen atom, a methoxy group, and a methylthio group, or a C3-C4 alkenyl group optionally having one or more atoms or groups selected from a group consisting of a halogen atom, a methoxy group, and a methylthio group; that is a compound represented by the formula (1-18-2):
wherein, Y 18 , X 1"2 , R 2"1 and R 8"1 are the same meanings as defined above;
a compound represented by the formula (1-18-2), wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-18-2) rich in a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-18-2) containing not less than 80 % of which is a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-18-2) containing not less than 90 % of which is a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-18-1), wherein r is 1, W is an oxygen atom, X is a C2-C4 alkyl group optionally having one or more atoms or groups selected from a group consisting of a halogen atom, a methoxy group, and a methylthio group, or a C3-C4 alkenyl group optionally having one or- more atoms or groups selected from a group consisting of a halogen atom, a methoxy group, and a methylthio group; that is a compound represented by the formula (1-18-3) :
wherein, Y 18 , X 1-2 , R 2 1 and R 8 1 are the same meanings as defined above;
a compound represented by the formula (1-18-3), wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-18-3) rich in a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-18-3) containing not less than 80 % of which is a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-18-3) containing not less than 90 % of which is a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation; a compound represented by formula (I), wherein Y is a 1,3- dioxanyl group optionally having an atom or a group .
selected from the group D;
a compound represented by formula (I), wherein Y is a 1,3- dioxanyl group optionally having a methyl group or an ethyl group;
a- compound represented by formula (I), wherein Y is a 1,3- dioxanyl group optionally having a methyl group or an ethyl group, and n is 1;
a compound represented by formula (I), wherein Y is a 1,3- dioxanyl group optionally having a methyl group or an ethyl group, and n is 1, R 1 , R 3 , R 4 , R 5 , R 6 and R 7 are hydrogen atoms, R 2 is a hydrogen atom or a methyl group, and R 8 is a hydrogen atom or a methyl group; that is a compound
represented by the formula (1-19-1):
wherein, Y 19 is a 1,3-dioxanyl group optionally having a methyl group or an ethyl group, R 2-1 , R 8"1 , X, W and r are the same meanings as defined above;
a compound represented by the formula (1-19-1), wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-19-1) rich in a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation; a compound represented by the formula (1-19-1) containing not less than 80 % of which is a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-19-1) containing not less than 90 % of which is a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-19-1), wherein r is 0, X is a C2-C4 alkyl group optionally having one or more atoms or groups selected from a group consisting of a halogen atom, a methoxy group, and a methylthio group, or a C3-C4 alkenyl group optionally having one or more atoms or groups selected from a group consisting of a halogen atom, a methoxy group, and a methylthio group; that is a compound represented by the formula (1-19-2) :
wherein, Y 19 , X 1-2 , R 2"1 and R 8"1 are the same meanings as defined above;
a compound represented by the formula (1-19-2) , wherein relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-19-2) rich in a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-19-2) containing not less than 80 % of which is a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-19-2) containing not less than 90 % of which is a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-19-1), wherein r is 1, W is an oxygen atom, X is a C2-C4 alkyl group
optionally having one or more atoms or groups selected from a group consisting of a halogen atom, a methoxy group, and a methylthio group, or a C3-C4 alkenyl group optionally having one or more atoms or groups selected from a group consisting of a halogen atom, a methoxy group, and a methylthio group; that is a compound represented by the formula (1-19-3) :
wherein, Y 19 , X 1"2 , R 2'1 and R 8"1 are the same meanings as defined above;
a compound represented by the formula (1-19-3), wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-19-3) rich in a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-19-3) containing not less than.80 % of which is a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation;
a compound represented by the formula (1-19-3) containing not less than 90 % of which is a compound, wherein a relative configulation of the double bond presented on the 2-position and 3-position of the carbonyl group is a E configlation . [0038]
Hereinafter, the processes of the present compounds are explained.
The present compound can be prepared by, for example, the following Production Method 1 or Production Method 2.
[0039]
(Production Method 1)
The present compound can be produced by reacting a compound represented by formula (4) and a compound
represented by formula (6) in presence of a condensation agent.
are
as defined above.
The reaction is performed in the presence of
condensation agent, and, if neccesary, in the presence of a base and a solvent.
Examples of the condensation agent to be used in the reaction include dicyclohexylcarbodiimide, l-ethyl-3- ( 3- dimethylaminopropyl) carbodiimide hydrochloride, and
benzotriazol-l-yloxytris (dimethylamino) -phosphonium
hexafluorophosphate .
Examples of the base to be used in the reaction include carbonates such as sodium carbonate and potassium carbonate; tertiary amines such as triethylamine , di-iso- propylethylamine, 1 , 8-diazabicyclo [ 5.4.0 ] undec-7-ene and 1 , 5-diazabicyclo [ 4.3.0 ] -5-nonene; and nitrogen-containing aromatic compounds such as pyridine and 4- dimethylaminopyridine .
. Examples of the solvent to be used in the reaction include hydrocarbons such as benzene-, toluene and hexane; ethers such as diethyl ether and tetrahydrofuran;
halogenated hydrocarbons such as dichloromethane, 1,2- dichloroethane and chlorobenzene ; and acid amides such as N, N-dimethylformamide .
The reaction time of the reaction is usually within a range of 5 minutes to 72 hours.
The reaction temperature of the reaction is usually within a range of -20 to 100°C.
In the reaction, a use molar ratio of the compound represented by the formula (4) to the compound represented by the formula (6) can be optionally set, but is preferably an equimolar or near equimolar ratio, for example, within a range of 0.5 mol to 3 mol of the compound represented by the formula (6), based on 1 mol of the compound represented by the formula (4) .
The condensing agent can be usually used in any amount within a range of 1 mol to excess amount, preferably a range of 1 mol to 3 mol, based on 1 mol of the compound represented by the formula (4) .
The base can be usually used in any amount within a range of 1 mol to excess amount, preferably within a range of 1 mol to 3 mol, based on 1 mol of the compound
represented by the formula (4) .
After completion of the reaction, the reaction mixture is usually subjected to a post-treatment operation of pouring the reaction mixture into water, followed by extraction with an organic solvent and further concentration, and thus the present compound can be obtained. The obtained the present compound can be purified by operations such as chromatography, recrystallization and distillation.
[0040]
(Production Method 2)
The present compound can be produced by reacting a compound represented by formula (5) and a compound
represented by formula (6) in presence of a base.
wherein, Z represents a chlorine atom, a bromine atom or an iodine atom; and , 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 performed in the presence of a base, and, usuallly in the presence of a solvent.
Examples of the base to be used in the reaction include carbonates such as sodium carbonate and potassium carbonate; tertiary amines such as triethylamine , di-iso- propylethylamine, 1 , 8-diazabicyclo [ 5.4.0 ] undec-7-ene and 1, 5-diazabicyclo [4.3.0] non-5-ene; and nitrogen-containing aromatic compounds such as pyridine and 4- dimethylaminopyridine .
Examples of the solvent to be used in the reaction include ethers such as 1,4-dioxane, tetrahydrofuran, ethyleneglycol dimethyl ether, tert-butyl methyl ether; aliphatic hydrocarbons such as hexane, heptane and octane; aromatic hydrocarbones such as toluene and xylene;
halogenated hydrocarbons such as chlorobenzene; esters such as ethyl acetate and butyl acetate; nitriles such as acetnitrile and butyronitorile; acid amides such as N,N- dimethylformamide; sulfoxides such as dimethylsulfoxide; and mixture thereof.
The reaction time of the reaction is usually within a range of 5 minutes to 72 hours.
The reaction temperature of the reaction is usually within a range of -20 to 100°C.
In the reaction, a use molar ratio of the compound represented by the formula (5) to the compound represented by the formula (6) can be optionally set, but is preferably an equimolar or near equimolar ratio, for example, within a range of 0.5 mol to 3 mol of the compound represented by the formula (6), based on 1 mol of the compound represented by the formula (5) .
The base can be usually used in any amount within a range of 1 mol to excess amount, preferably within a range of 1 mol to 3 mol, based on 1 mol of the compound
represented by the formula (5).
After completion of the reaction, the reaction mixture is usually subjected to a post-treatment operation of pouring the reaction mixture into water, followed by extraction with an organic solvent and further concentration, and thus the present compound can be obtained. The obtained the present compound can be purified by operations such as chromatography, recrystallization and distillation.
[0041]
Next, the processes of the intermediate compounds used for producing the present compound are explained.
[0042]
(Reference Production Method 1)
The compound represented by the formula (5) can be produced by reacting a compound represented by formula (4) and 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 performed in the presence or the absense of a solvent.
Examples of the halogenating agent to be used in the reaction include thionyl chloride, oxalyl chloride, and phosphorous oxychloride.
Examples of the solvent to be used in the reaction include ethers such as 1,4-dioxane, tetrahydrofuran
ethyleneglycol dimethyl ether and tert-butyl methyl, ether; aliphatic hydrocarbons such as hexane and heptane; aromatic hydrocarbons such as toluene and xylene; halogenated hydrocarbons such as chlorobenzene ; and mixture thereof.
The reaction time of the reaction is usually within a range of 5 minutes to 24 hours.
The reaction temperature of the reaction is usually within a range of 0 to 100°C.
The halogenating agent can be usually used in any amount within a range of 1 mol to excess amount, preferably within a range of 1 mol to 5 mol, based on 1 mol of the compound represented by the formula (4).
After completion of the reaction, the reaction mixture is usually subjected to a post-treatment operation of concentrating the reaction mixture, and thus the compound represented by the formula (5) can be obtained. Usually, the obtained compound represented by the formula (.5) can be used for following process without further purification, but also, as necessary, can be purified by distillation.
[0043]
(Reference Production Method 2)
The compound represented by the formula (4) can be produced by hydrolyzing a compound represented by formula (3) in the presence of a base.
wherein, R a represents a methyl group or an ethyl group; ,
X, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and r are as defined above.
The reaction is performed in the presence of a base, and in the presence of water and an organic solvent.
Examples of the base to be used in the reaction include alkali metal hydroxides such as lithium hydroxide, sodium hydroxide and potassium hydroxide.
Examples of the organic solvent to be used in the reaction include ethers such as 1,4-dioxane,
tetrahydrofuran, ethyleneglycol dimethyl ether, and tert- butyl methyl ether; aromatic hydrocarbons such as toluene and xylene; halogenated hydrocarbons such as chlorobenzene nitriles such as acetnitrile and butyronitorile; alcohols such as methanol ethanol and propanol; and mixture thereof
The reaction time of the reaction is usually within a range of ' 5 minutes to 72 hours.
The reaction temperature of the reaction is usually within a range of 0 to 100°C. The base can be usually used in any amount within a range of 1 mol to excess amount, preferably within a range of 1 mol to 5 mol, based on 1 mol of the compound
represented by the formula (3) .
After completion of the reaction, the reaction mixture is usually subjected to a post-treatment operation of pouring acidic water (e.g. hydrochloric acid), followed by extraction with an organic solvent, drying, and further concentration, and thus the compound represented by the formula (4) can be obtained. Although obtained compound represented by the formula (4) can be purified by operations such as chromatography, recrystallization and distillation, the obtained compound represented by the formula (4) usually can be used for following process without further purification
[0044]
(Reference Production Method 3)
A compound represented by the formula (3-1), of the compound represented by the formula (3) , wherein r is 0, can be produced by reacting a compound represented by formula (1) and a compound represented by the formula (2-a) or a compound represented by the 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 performed in the presence of a base, and, usuallly in the presence of a solvent.
Examples of the base to be used in the reaction include alkali metal alkoxide such as sodium methoxide and potassium tert-butoxide ; alkali metal hydride such as sodium hydride and potassium hydride; and alkali metal amides such as sodium bis (trimethylsilyl ) amide, lithium bis (trimethylsilyl) amide and lithium diisopropylamide.
Examples of the solvent to be used in the reaction include hydrocarbons such as benzene, . toluene and hexane; ethers such as diethyl ether and tetrahydrofuran; and mixture thereof. The reaction time of the reaction is usually within a range of 5 minutes to 72 hours.
The reaction temperature of the reaction is usually within a range of -80 to 100°C.
In the reaction, a use molar ratio of the compound represented by the formula (2-a) or the compound
represented by the formula (2-b) to the compound
represented by the formula (1) can be optionally set, but is preferably an equimolar or near equimolar ratio, for example, within a ' range of 0.5 mol to . 3 mol of the compound represented by the formula (2-a) or the compound
represented by the formula (2-b) , based on 1 mol of the compound represented by the formula (1) .
The base can be usually used in any amount within a range of 1 mol to excess amount, preferably within a range of 1 mol to 5 mol, based on 1 mol of the compound
represented by the formula (2-a) or the compound
represented by the formula (2-b) .
After completion of the reaction, the reaction mixture is usually subjected to a post-treatment operation of pouring the reaction mixture into water, followed by extraction with an organic solvent and further concentration, and thus the compound represented by the formula (3-1) can be obtained. The obtained compound represented by the formula (3-1) can be purified by operations such as chromatography, recrystallization and distillation.
[0045]
(Reference Production Method 4)
A compound represented by the formula (3-1), of the compound represented by the formula (3), wherein r is 0, can be produced by reacting a compound represented by formula (7) and a compound represented by the formula (8) in the resence 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 performed in the presence of a base, and, usuallly in the presence of a solvent.
Examples of the base to be used in the reaction include alkali metal alkoxide such as sodium methoxide and potassium tert-butoxide; alkali metal hydride such as sodium hydride and potassium hydride; and alkali metal amides such as sodium bis (trimethylsilyl) amide, lithium bis (trimethylsilyl) amide and lithium diisopropylamide.
Examples of the solvent to be used in the reaction . include hydrocarbons such as benzene, toluene and hexane; ethers such as diethyl ether and tetrahydrofuran; and mixture thereof.
The reaction time of the reaction is usually within a range of 5 minutes to 72 hours.
The reaction temperature of the reaction is usually within a range of -80 to 100°C.
In the reaction, a use molar ratio of the compound represented by the formula (8) to the compound represented by the formula (7) can be optionally set, but is preferably an equimolar or near equimolar ratio, for example, within a range of 0.5 mol to 3 mol of the compound represented by the formula (8), based on 1 mol of the compound represented by the formula (7) .
The base can be usually used in any amount within a range of 1 mol to excess amount, preferably within a range of 1 mol to 5 mol, based on 1 mol of the compound
represented by the formula (8) .
After completion of the reaction, the reaction mixture is usually subjected to a post-treatment operation of pouring the reaction mixture into water, followed by extraction with an organic solvent and further concentration, and thus the compound represented by the formula (3-1) can be obtained. The obtained compound represented by the formula (3-1) can be purified by operations such as chromatography, recrystallization and distillation .
[0046]
(Reference. Production Method 5)
A compound represented by the formula (3-2), of the compound represented by the formula (3), wherein r is 1, can be produced by following methods.
wherein, R b represents a methyl group or an ethyl group, W, X, R a , R 1 , R 2 , R 3 , R 4 , R 5 and R 6 are as defined above.
[0047]
(Process 5-1)
A compound represented by the formula (12) can be produced by reacting a compound represented by formula (12) in the presence of water and an acid.
The reaction is performed in the presence of an acid, and in the presence of water and an organic solvent.
Examples of the acid to be used in the reaction include inorganic acids such as hydrochloric acid and sulfuric acid; and organic acids such as methanesulfonic acid and p-toluenesulfonic acid.
Examples of the organic solvent to be used in the reaction include ethers such as 1,4-dioxane,
tetrahydrofuran, ethyleneglycol dimethyl ether, and tert- butyl methyl ether; aromatic hydrocarbons such as toluene and xylene; halogenated hydrocarbons such as chlorobenzene ; nitriles such as acetnitrile and butyronitorile; alcohols such as methanol ethanol and propanol; ketones such as acetone and methylisobutylketone; and mixture thereof.
The reaction time of the reaction is usually within a range of 5 minutes to 24 hours.
The reaction temperature of the reaction is usually within a range of 0 to 100°C.
The acid can be used in any amount within a range of 1 mol to excess amount based on 1 mol of the compound
represented by the formula (12) .
After completion of the reaction, the reaction mixture is usually subjected to a post-treatment operation of pouring the reaction mixture into water, followed by extraction with an organic solvent and further concentration, and thus the compound represented by the formula (12) can be obtained. The obtained compound represented by the formula (12) can be purified by operations such as chromatography, recrystallization and distillation .
[0048]
(Process 5-2)
The compound represented by the formula (3-2) can be produced by reacting a compound represented by formula (12) and a compound represented by formula (8) in presence of a base.
The reaction is performed in the presence of a base, and usually in the presence of a solvent.
Examples of the base to be used in the reaction .
include alkali metal alkoxide such as sodium methoxide and. potassium tert-butoxide ; alkali metal hydride such as sodium hydride and potassium hydride; and alkali metal amides such as sodium bis (trimethylsilyl ) amide, lithium bis (trimethylsilyl) amide and lithium diisopropylamide.
Examples of the solvent to be used in the reaction include hydrocarbons such as benzene, toluene and xylene; ethers such as diethyl ether and tetrahydrofuran; and mixture thereof. The reaction time of the reaction is usually within a range of 5 minutes to 72 hours.
The reaction temperature of the reaction is usually within a range of -80 to 100°C.
In the reaction, a use molar ratio of the compound represented by the formula (8) to the compound represented by the formula (12) can be optionally set, but is
preferably an equimolar or near equimolar ratio, for example, within a range of 0.5 mol to 3 mol of the compound represented by the formula (8), based on 1 mol of the compound represented by the formula (12).
The base can be used in any amount within a range of 1 mol to excess amount, preferably within a range of 1 to 5 mol, based on 1 mol of the compound represented by the formula (12) .
After completion of the reaction, the reaction mixture is usually subjected to a post-treatment operation of pouring the reaction mixture into water, followed by extraction with an organic solvent and further concentration, and thus the compound represented by the formula (3-2) can be obtained. The obtained compound represented by the formula (3-2) can be purified by operations such as chromatography, recrystallization and distillation.
[0049] (Reference Production Method 6)
A compound represented by the formula (11-1), of the compound represented by the formula (11), wherein W is an oxygen atom or a sulfur atom, can be produced by reacting a compound represented by formula (9) and a compound
represented by the formula (10) in the presence of a base.
( 9 ) ( 1 1 - 1 )
wherein, W 1 represents an oxygen atom or sulfur atom; R b represents a methyl group or an ethyl group, L represents a leaving group such as a chlorine atom, a bromine atom, an iodine atom and a methanesulfonyl group; and X, R 4 , R 5 and
R 6 represent are as defined above.
The reaction is performed usually in the presence of a base, and usually in the presence of a solvent.
Examples of the base to be used in the reaction include inorganic bases such as sodium hydride, sodium hydroxide, potassium hydroxide and potassium carbonate; alkali metal alkoxides such as sodium methoxide and
potassium tert-butoxide; and organic bases such as
triethylamine, 1, -diazabicyclo [2.2.2] octane, 1,8- diazabicyclo [5.4.0] -7-undecene .
Examples of the solvent to be used in the reaction include ethers such as diethyl ether, tetrahydrofuran and dimethoxyethane; acid amides such as N, N-dimethylformamide; organic sulfurs such as dimethylsulfoxide and sulfolane; aliphatic hydrocarbons such as hexane and heptane; aromatic hydrocarbons such as toluene and xylenes; halogenated hydrocarbons such as 1 , 2-dichloroethane and chlorobenzene ; water; and mixture thereof.
The reaction time of the reaction is usually within a range of 5 minutes to 72 hours.
The reaction temperature of the reaction is usually within a range of 0 to 100°C.
In the reaction, a use molar ratio of the compound represented by the formula (10) to the compound represented by the formula (9) can be optionally set, but is preferably an equimolar or near equimolar ratio, for example, within a range of 1 mol to 3 mol of the compound represented by the formula. (10), based on 1 mol of the compound represented by the formula ( 9) .
The base can be used in any amount within a range of 1 mol to excess amount, preferably within a range of 1 to 3 mol, based on 1 mol of the compound represented by the formula ( 10 ) .
After completion of the reaction, the reaction mixture is usually, subjected to a post-treatment operation of pouring the reaction mixture into water, followed by extraction with an organic solvent and further concentration, and thus the compound represented by the formula (11-1) can be obtained. The obtained compound represented by the formula (11-1) can be purified by operations such as chromatography, recrystallization and distillation.
[0050]
(Reference Production Method 7)
A compound represented by the formula (11-so), of the compound represented by the formula (11), wherein W is - S(0) t -, and u is 1 or 2, can be produced by oxidizing a compound represented by formula (11-s), of the compound represented by the formula (11-1) , wherein W 1 is a sulfur atom.
wherein, ul represents 1 or 2; and X, R , R 4 , R 5 and R 6 are as defined above.
The reaction is performed in the presence of a solvent. Examples of oxidizing agent to be used in the reaction include organic peroxides such as acetic peroxide,
trifluoroacetic peroxide and m-chloroperbenzoic acid;
molecular halogens such as molecular chlorine and molecular bromine; halogen-containing imides such as N- chlolrosuccinimide ; perhaloic acids such as perchloric acid (or salts thereof) , periodic acid (or salts thereof) ;
permanganates such as potassium permanganate; chromates such as potassium chromate; peroxysulfates such as
potassium peroxymonosulfate; and hydrogen peroxide.
Examples of the solvent to be used in the reaction include alcohols such as methanol and ethanol; halogenated hydrocarbons such as dichloromethane and chloroform;
aromatic hydrocarbons such as toluene and xylene; aliphatic carboxylic acids such as acetic acid and trifluoroacetic acid; water; and mixture thereof.
The reaction time of the reaction is usually within a range of 5 minutes to 24 hours.
The reaction temperature of the reaction is usually within a range of -80 to 100°C.
In the reaction, a use molar ratio of the oxidizing agent to the compound represented by the formula (11-s) can be optionally set, but is preferably . an equimolar or near equimolar ratio, for example, within a range of 0.5 mol to 3 mol of the oxidizing agent, based on 1 mol of the
compound represented by the formula (11-s).
After completion of the reaction, the reaction mixture is usually subjected to a post-treatment operation of pouring the reaction mixture into water, followed by extraction with an organic solvent and further concentration, and thus the compound represented by the formula (11-so) can be obtained. The obtained compound represented by the formula (11-so) can be purified by operations such as chromatography, recrystallization and distillation .
[0051]
(Reference Production Method 8)
A compound represented by the formula (3-2-1) , of the compound represented by the formula (3), wherein r is 1, and W is an oxygen atom or a sulfur atom, can be produced by following methods.
wherein, W 1 , L, X, R a , R 1 , R 2 , R 3 , R 4 , R 5 and R 6 are as defined above.
[0052]
(Process 8-1-1)
A compound represented by the formula (16) can be produced by reacting a compound represented by formula and a compound represented by the formula (10) in the presence of a base.
The reaction is performed in the presence of a base, and usually in the presence of a solvent.
Examples of the base to be used in the reaction include inorganic bases such as sodium hydride, sodium hydroxide, potassium hydroxide and potassium carbonate; alkali metal alkoxides such as sodium methoxide and
potassium tert-butoxide; and organic bases such as
triethylamine, 1 , 4-diazabicyclo [2.2.2 ] octane, 1,8- diazabicyclo [5.4.0] -7-undecene .
Examples of the solvent to be used in the reaction include ethers such as diethyl ether, tetrahydrofuran and dimethoxyethane; acid amides such as N, N-dimethylformamide; organic sulfurs such as dimethylsulfoxide and sulfolane; aliphatic hydrocarbons such as hexane and heptane; aromatic hydrocarbons such as toluene and xylenes; halogenated hydrocarbons such as 1, 2-dichloroethane and chlorobenzene, water; and mixture thereof.
The reaction time of the reaction is usually within a range of 5 minutes to 24 hours.
The reaction temperature of the reaction is usually within a range of 0 to 100°C.
In the reaction, a use molar ratio of the compound represented by the formula (10) to the compound represented by the formula (14) can be optionally set, but is preferably an equimolar or near equimolar ratio, for example, within a range of 1 mol to 3 mol of the compound represented by the formula (10), based on 1 mol of the compound represented by the formula (14).
The base can be used in any amount within a range of 1 mol to excess amount, preferably within a range of 1 to 3 mol, based on 1 mol of the compound represented by the formula ( 10 ) .
After completion of the reaction, the reaction mixture is usually subjected to a post-treatment operation of pouring the reaction mixture into water, followed by extraction with . an organic solvent and further concentration, and thus the compound represented by the formula (16) can be obtained. The obtained compound represented by the formula (16) can be purified by operations such as chromatography, recrystallization and distillation .
[0053]
(Process 8-1-2)
A. compound represented by the formula (16) can be produced by reacting a compound represented by formula (15) and a compound represented by the formula (17) in the .
presence of a base.
The reaction is performed in the presence of a base, and usually in the presence of a solvent. Examples of the base to be used in the reaction include inorganic bases such as sodium hydride, sodium hydroxide, potassium hydroxide and potassium carbonate;
alkali metal alkoxides such as sodium methoxide and
potassium tert-butoxide; organic bases such as
triethylamine, 1, 4-diazabicyclo [2.2.2] octane, 1,8- diazabicyclo [5.4.0] -7-undecene .
Examples of the solvent to be used in the reaction include ethers such as diethyl ether, tetrahydrofuran and dimethoxyethane; acid amides such as N, N-dimethylformamide; organic sulfurs such as dimethylsulfoxide and sulfolane; aliphatic hydrocarbons such as hexane and heptane; aromatic hydrocarbons such as toluene and xylenes; halogenated hydrocarbons such as 1 , 2-dichloroethane and chlorobenzene; water; and mixture thereof.
The reaction time of the reaction is usually within a range of 5 minutes to 24 hours.
The reaction temperature of the reaction is usually within a range of 0 to 100°C (provided that a boiling point of the solvent to be used in the reaction is less than 100°C, the reaction temperature of the reaction is usually within a range of 0°C to the boiling point thereof) .
In the reaction, a use molar ratio of the compound represented by the formula (15) to the compound represented by the formula (17) can be optionally set, but the compound represented by the formula (15) is used preferably an excessmolar relative to the compound represented by the formula (17), for example, within a range of 3 to 5 mol of the compound represented by the formula (15) , based on 1 mol of the compound represented by the formula (17).
The base can be used in any amount within a range of 1 mol to excess amount, preferably within a range of 1 to 3 mol, based on 1 mol of the compound represented by the formula ( 15) .
After completion of the reaction, the reaction mixture is usually subjected to a post-treatment operation of pouring the reaction mixture into water, followed by extraction with an organic solvent and further concentration, and thus the compound represented by the formula (16) can be obtained. The obtained compound represented by the formula (16) can be purified by operations such as chromatography, recrystallization and distillation.
[0054]
(Process 8-2)
A compound represented by the formula (18) can be produced by oxidizing a compound represented by formula (16).
Examples of method of oxidizing include as follows: (1) a method using an activated manganese dioxide; (2) a method using a pyridinium chlorochromate or a pyridinium dichromate;
(3) a method using a D SO-oxidation (e.g. Swern oxidation)
(4) a method using a Dess-Martin Reagent;
(5) a method using a TEMPO (2, 2, 6, 6-tetramethylpiperidine 1-oxyl) reagent.
As an example, a concrete example of " (1) A method using an activated manganese dioxide" is as follows:
The reaction is performed in the presence of a solvent
Examples of the solvent to be used in the reaction include aliphatic hydrocarbons such as hexane and heptane; aromatic hydrocarbons such as toluene and xylenes;
halogenated hydrocarbons such as dichloromethane, 1,2- dichloroethane and chlorobenzene ; ketones such as acetone and methylisobutylketone .
The reaction time of the reaction is ' usually within a range of 5 minutes to 24 hours.
The reaction temperature of the reaction is usually within a range of 0 to 100°C.
In the reaction, a use amount ratio of the activated manganese dioxide to the compound represented by the formula (16) is usually within a range of 1 part to 10 parts by weight, preferably 3 parts to 5 parts by weight, based on 1 part by weight of the compound represented by the formula ( 18 ) . After completion of the reaction, the reaction mixture is subjected to an operation of filtration, then, the obtained filtrate is concentrated, thus the compound represented by the formula (18) can be obtained. The obtained compound represented by the formula (18), as necessary, can be purified by operations such as
chromatography, recrystallization and distillation.
[0055]
(Process 8-3)
A compound represented by the formula (3-2-1) can be produced by reacting a compound represented by formula ■ (18); and the compound represented by the formula (2-a) or the compound represented by the formula (2-b) in the presence of a base.
[0056]
The reaction is performed in the presence of a base, and usually in the presence of a solvent.
Examples of the base to- be used in the reaction include alkali metal alkoxide such as sodium methoxide and potassium tert-butoxide ; alkali metal hydride such as sodium hydride and potassium hydride; and alkali metal amides such as sodium bis (trimethylsilyl ) amide, lithium bis (trimethylsilyl) amide and lithium diisopropylamide.
Examples of the solvent to be used in the reaction include hydrocarbons such as benzene, toluene and hexane; ehters such as diethyl ehter and tetrahydrofuran; and mixture thereof.
The reaction time of the reaction is usually within a range of 5 minutes to 72 hours.
The reaction temperature of the reaction is usually within a range of -80 to 100°C.
In the reaction, a use molar ratio of the compound ' represented by the formula (2-a) or the compound
represented by the formula (2-b) to the compound
represented by the formula (18) can be optionally set, but is preferably an equimolar or near equimolar ratio, for example, within a range of 0.5 mol to 3 mol of the compound represented by the formula (2-a) or the compound
represented by the formula (2-b) , based on 1 mol of the compound represented by the formula (18).
' The base can be usually used in any amount within a range of 1 mol to excess amount, preferably within a range of 1 mol to 5 mol, based on 1 mol of the compound
represented by the formula (2-a) or the compound
represented by the formula (2-b) .
After completion of the reaction, the reaction mixture is usually subjected to a post-treatment operation of pouring the reaction mixture into water, followed by extraction with an organic solvent and further concentration, and thus the compound represented by the formula (3-2-1) can be obtained. The obtained compound represented by the formula (3-2-1) can be purified by operations such as chromatography, recrystallization and distillation.
[0057]
(Reference Production Method 9)
A compound represented by the formula (6) can be produced by following methods.
acid,
(20)
wherein, L, Y, R 7 , R 8 and n are as defined avobe .
[0058]
(Reference Production Method 10)
Also, a compound represented by the formula (6) can be produced by the following methods.
( 1 9 ) (Process 10-1 ) ( 2 1 ) (Process 10-2) ( 6 ) wherein, L, Y, R 7 , R 8 and n are as defined above.
[0059]
( Process 10-1 )
A compound represented by the formula (21) can be produced by reacting a compound represented by the formula (19) and sodium azide.
The reaction is usually performed in the presence of a solvent .
Examples of the solvent to be used in the reaction include ethers such as diethyl ether, tetrahydrofuran and dimethoxyethane; acid amides such as N, N-dimethylformamide; organic sulfurs such as dimethylsulfoxide and sulfolane; aliphatic hydrocarbons such as hexane and heptane; aromatic hydrocarbons such as toluene and xylenes; halogenated hydrocarbons such as 1 , 2-dichloroethane and chlorobenzene ; water; and mixture thereof.
The reaction time of the reaction is usually within a range of 5 minutes to 72 hours.
The reaction temperature of the reaction is usually within a range of 0 to 100°C (provided that a boiling point of the solvent to be used in the reaction is less than 100°C, the reaction temperature of the reaction is usually within a range of 0°C to the boiling point thereof) .
In the reaction, a use molar ratio of sodium azide to the compound represented by the formula (19) can be
optionally set, but is preferably an equimolar or near equimolar ratio, for example, within a range of 1 mol to 3 mol of sodium azide, based on 1 mol of the compound
represented by the formula (19) . After completion of the reaction, the reaction mixture is usually subjected to a post-treatment operation of pouring the reaction mixture into water, followed by extraction with an organic solvent and further concentration, and thus the compound represented by the formula (21) can be obtained. The obtained compound represented by the formula (21) can be purified by operations such as chromatography, recrystallization and distillation .
[0060]
(Process 10-2)
A compound represented by the formula (6) can be produced by reductive reacting a compound represented by formula (21) .
Examples ' of reductive reaction include as follows:
(1) a method using a hydrogenolysis catalyst;
(2) a method using a metal hydride such as sodium
borohydride and lithiumalminium hydride.
As an example, Concrete example of "(1) a method using a hydrogenolysis catalyst" is as follows:
The reaction is usually performed under .hydrogen gas atmophere / usually in the presence of a solvent.
Examples of the hydrogenolysis catalyst to be used in the reaction include transition metal compound such as palladium carbon, palladium hydroxide, Raney™ nickel and platinum oxide.
Examples of the solvent to be used in the reaction include alcohols such as methanol, ethanol and propanol; esters ethyl acetate and butyl acetate; ethers such as tetrahydrofuran and 1,4-dioxane; and mixture thereof.
The reaction is usually performed in a hydrogen gas atmosphere under 1 to 100 atmospheric pressures.
The reaction time of the reaction is usually within a range of 5 minutes to 24 hours.
The reaction temperature of the reaction is usually within a range of -20 to 100°C (provided that a boiling point of the solvent to be used in the reaction is less than 100°C, the reaction temperature of the reaction is usually within a range of -20°C to the boiling point thereof) .
The amount of the hydrogenolysis catalyst to be used in this reaction is usually within a range of 0.001 to 0.5 mol, based on 1 mol of the compound represented by the formula (21) .
After completion of the reaction, the reaction mixture is subjected to an operation of filtration, then, the obtained filtrate is concentrated, thus the compound represented by the formula (6) can be obtained. The obtained compound represented by the formula (6), as necessary, can be purified by operations such as chromatography, recrystallization and distillation.
[0061]
(Reference Production Method 11)
A compound represented by the formula (6-1), of th compound represented by the formula (6), wherein R 7 and are hydrogen atoms, can be produced by the following, methods .
rocess - (Process 11-1) wherein, M represents potassium or sodium; and
nl represent; and L and Y are as defined above.
[0062]
(Process 11-1)
A compound represented by the formula (22) can be produced by reacting a compound represented by formula (19 h) and a metal cyanide (MCN) .
The reaction is usually performed in the presence of solvent.
Examples of the metal cyanide include sodium cyanide and potassium cyanide.
Examples of the solvent to be used in the reaction include ethers such as diethyl ether, tetrahydrofuran and dimethoxyethane; acid amides such as N, N-dimethylformamide organic sulfurs such as dimethylsulfoxide and sulfolane; aliphatic hydrocarbons such as hexane and heptane; aromatic hydrocarbons such as toluene and xylenes; halogenated hydrocarbons such as 1 , 2-dichloroethane and chlorobenzene; water; and mixture thereof.
The reaction time of the reaction is usually within a range of 5 minutes to 24 hours.
The reaction temperature of the reaction is usually within a range of 0 to 100°C.
In the reaction, a use molar ratio of the metal cyanide to the compound represented by the formula (19-h) can be optionally set, but is preferably an equimolar or near equimolar ratio, for example, within a range of 1 mol to 3 mol of the metal cyanide, based on 1 mol of the compound represented by the formula (19-h).
After completion of the reaction, the reaction mixture is usually subjected to a post-treatment operation of pouring the reaction mixture into water, followed by extraction with an organic solvent and further concentration, and thus the compound represented by the formula (22) can be obtained. The obtained compound represented by the formula (22) can be purified by operations such as chromatography, recrystallization and distillation .
[0063]
(Process 11-2) A compound represented by the formula (6) can be produced by reductive reacting a compound represented by formula (22) .
Examples of reductive reaction include as follows:
(1) a method using a hydrogenolysis catalyst;
(2) a method using a metal hydride such as sodium
borohydride and lithiumalminium hydride.
As an example, a concrete example of "(1) a method using a hydrogenolysis catalyst" is as follows:
The reaction is usually performed under hydrogen gas atmophere, usually in the presence of a solvent.
Examples of the hydrogenolysis catalyst to be used in the reaction include transition metal compound , such as palladium carbon, palladium hydroxide, Raney™ nickel and platinum oxide.
Examples of the solvent to be used in the reaction include alcohols such as methanol, ethanol and propanol; esters ethyl acetate and butyl acetate; ethers such as tetrahydrofuran and 1,4-dioxane.
The reaction is usually performed in a hydrogen gas atmosphere under 1 to 100 atmospheric pressures.
The reaction is . erformed, if necessry, in presence o an ammonia.
The reaction time of the reaction is usually within a range of 5 minutes to 24 hours. The reaction temperature of the reaction is usually within a range of -20 to 100°C (provided that a boiling point of the solvent to be used in the reaction is less than 100°C, the reaction temperature of the reaction is usually within a range of -20°C to the boiling point thereof) .
The amount of the hydrogenolysis catalyst to be used in this reaction is usually within a range of 0.001 to 0.5 mol, based on 1 mol of the compound represented by the formula (22) .
After completion of the reaction, the reaction mixture is subjected to an operation of filtration, then, the obtained filtrate is concentrated, thus the compound represented by the formula (6) can be obtained. The obtained compound represented by the formula (6), as necessary, can be purified by operations such as
chromatography, recrystallization and distillation.
[0064]
The present compounds are effective against harmful arthropods (e.g. harmful insects and mites), nematodes, and mollusks. The specific examples of the pests are as follows. The specific examples of the harmful arthropods are as follows . Hemiptera: planthoppers such as Laodelphax striatellus, Nilaparvata lugens, and Sogatella furcifera, leafhoppers such as Nephotettix cincticeps, and Nephotettix virescens, aphids such as Aphis gossypii, and Myzus persicae, plant bugs such as Nezara antennata, Riptortus clavetus,
Eysarcoris lewisi, Eysarcoris parvus, Plautia stali,
Halyomorpha mista, Stenotus rubrovittatus , and Tribonotylus ruficorinis, white flies such as Trialeurodes vaporariorum, and Bemisia argentifolii, scales such as Aonidiella
aurantii, Comstockaspis perniciosa, Unaspis citri,
Ceroplastes rubens, and Icerya purchasi, lace bugs, bed bugs such as Cimex lectularius, jumping plantlice and so on;
[0065]
Lepidoptera: Pyralidae such as Chilo suppressalis, Cnaphalocrocis medinalis, . Notarcha derogata, and Plodia interpunctella, Spodoptera litura, Pseudaletia separata, Noctuidae such as Trichoplusia spp., Heliothis spp., and Earias spp., Pieridae such as Pieris rapae, Tortricidae such as Adoxopheys spp., Grapholita molesta, Adoxophyes orana fasciata, and Cydia pomonella, Carposinidae such as Carposina niponensis, Lyonetiidae such as Lyonetia spp., Lymantriidae such as Lymantria spp., Lymantriidae such as Euproctis spp., Yponameutidae such as Plutella xylostella, Gelechiidae such as Pectinophora gossypiella, Arctiidae such as Hyphantria cunea, Tineidae such as Tinea . translucens, and Tineola bisselliella, and so on;
[0066]
Diptera: Culex spp. such as Culex pipiens pallens, Culex tritaeniorhynchus , and Culex quinquefasciatus , Aedes spp. such as Aedes aegypti, and Aedes albopictus, Anopheles spp. such as Anopheles sinensis, Chironomidae, Muscidae such as Musca domestica, and Muscina stabulans,
Calliphoridae, Sarcophagidae, little housefly, Anthomyiidae such as Delia platura, .and Delia antiqua, Agromyzidae such as Liriomyza trifolii, Tephritidae, Drosophilidae,
Phoridae such as Megaselia spiracularis , Psychodidae such as Clogmia albipunctata, Simuliidae, Tabanidae, Stomoxyidae, and so on;
[0067]
Coleoptera: Diabrotica spp. such as Diabrotica
virgifera virgifera, and Diabrotica undecimpunctata howardi, Sca abaeidae such as Anomala cuprea, and Anomala rufocuprea, Curculionidae such as Sitophilus zeamais, Lissorhoptrus oryzophilus, and Callosobruchuys chienensis, Tenebrionidae such as Tenebrio molitor, and Tribolium castaneum,
Chrysomelidae such as Oulema oryzae, Aulacophora femoralis, Phyllotreta striolata, and Leptinotarsa decemlineata,
Dermestidae such as Dermestes maculates, Anobiidae,
Epilachna spp. such as Epilachna vigintioctopunctata,
Lyctidae, Bostrychidae, Ptinidae, Cerambycidae, Paederus fuscipes, and so. on;
[0068]
Blattodea: Blattella germanica, Periplaneta fuliginosa, Periplaneta americana, Periplaneta brunnea, Blatta
orientalis, and so on;
[0069]
Thysanoptera : Thrips palmi, Thrips tabaci,
Frankliniella occidentalis, ^ Frankliniella intonsa, and so on;
Hymenoptera : Formicidae such as Monomorium pharaosis, Formica fusca japonica, Ochetellus glaber, Pristomyrmex pungens, and Pheidole noda, Vespidae, Bethylidae,
Tenthredinidae such as Athalia japonica, and so on;
[0070]
Orthoptera: mole crickets, grasshoppers, crikets, and so on;
Shiphonaptera : Ctenocephalides felis, Ctenocephalides canis, Pulex irritans, Xenopsylla cheopis, and so on;
Anoplura: Pediculus humanus corporis, Phthirus pubis, Haematopinus eurysternus, Dalmalinia ovis, haematopinus eurysternus, and so on;
Isoptera: Reticulitermes spp. such as Reticulitermes speratus, Coptotermes formosanus, Reticulitermes flavipes, Reticulitermes hesperus, Reticulitermes virginicus,
Reticulitermes tibialis, and Heterotermes aureus, Incisitermes spp. such as Incisitermes minor, and
Zootermopsis spp. such as Zootermopsis nevadensis, and so on;
[0071]
Acarina: Tetranychidae such as Tetranychus urticae, Tetranychus kanzawai, Panonychus citri, Panonychus ulmi, and Oligonychus spp., Eriophyidae such as Aculops lycopers, Aculops pelekassi, and Aculus schlechtendali, Tarsonemidae such as Polyphagotarsonemus latus, Tenuipalpidae,
Tuckerellidae, Ixodidae such as Haemaphysalis longicornis, Haemaphysalis flava, Dermacentor variabilis, Haemaphysalis flava, Dermacentor taiwanicus, Ixodes ovatus, Ixodes persulcatus , Ixodes scapularis, Boophilus microplus,
Amblyomma americanum, and Rhipicephalus sanguineus,
Acaridae such as Tyrophagus putrescentiae, Dermanyssidae such as Dermatophagoides farinae, Dermatophagoides
ptrenyssnus, Cheyletidae such as Cheyletus eruditus,
Cheyletus malaccensis, and Cheyletus moorei, chicken mite such as Ornithonyssus bacoti, Ornithonyssus sylvairum, and Dermanyssus gallinae, Trombiculidae such as Leptotrombidium akamushi, and so on;
Araneae: Japanese foliage spider (Chiracanthium japonicum), redback spider (Latrodectus hasseltii), and so on;
[0072] Chilopoda ' : centipedes such as Thereuonema hilgendorfi, and Scolopendra subspinipes, and so on;
Diplopoda: millipedes such as Oxidus gracilis,
Nedyopus tambanus, and so on;
Isopoda: Armadillidium vulgare, and so on;
Gastropoda: Limax marginatus, Limax flavus, and so on.
[0073]
The harmaful arthropod control agent of the present invention comprises the present compound and an inert carrier. The harmaful arthropod control agent of the present invention is generally formulated into, for example, an emulsion, an oil solution, a powder, a granule, a wettable powder, a flowable formulation, a microcapsule agent, an aerosol, a smoking agent, a toxic bait, or a resin formulation by mixing the present compound and an inert carrier (e.g. solid carrier, liquid carrier, and . gas carrier), and, if necessary, adding a surfactant or other formulation additives.
The harmaful arthropod control agent of . the present invention generally contains the present compound in an amount of 0.01 wt% to 95 wt%.
[0074]
The solid carrier used herein includes, for example, fine powders and granular materials made from, for example, clays (e.g. kaolin clay, diatomaceous earth, bentonite, Fubasami clay, and acid clay) ; synthetic hydrated silicon oxide; talc; ceramic; other inorganic minerals (e.g. sericite, quartz, sulfur, activated charcoal, calcium carbonate, and hydrated silica) ; and chemical fertilizers (e.g. ammonium sulfate, ammonium phosphate, ammonium nitrate, urea, and ammonium chloride) .
[0075]
The liquid carrier used herein includes, for example, water; alcohols (e.g. methanol, ethanol, isopropyl alcohol, butanol, hexanol, benzyl alcohol, ethylene glycol,
propylene glycol, and phenoxy ethanol); ketones (e.g.
acetone, methyl ethyl ketone, and cyclohexanone ) ; aromatic hydrocarbons (e.g. toluene, xylene, ethylbenzene,
dodecylbenzene, phenylxylylethane, and methylnaphthalene) ; aliphatic hydrocarbons (e.g. hexane, cyclohexane, kerosene, and light oil); esters (e.g. ethyl acetate, butyl acetate, isopropyl myristate, ethyl oleate, diisopropyl adipate, diisobutyl adipate, and propylene glycol monomethyl ether acetate); nitriles (e.g. acetonitrile and
isobutyronitrile) ; ethers (e.g. 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, and 3-methoxy-3-methyl-l-butanol ) ; acid amides " (e.g. N, N-dimethylformamide and N,N- dimethylacetamide) ; halogenated hydrocarbons (e.g.
dichloromethane, trichloroethane, and carbon
tetrachloride); sulfoxides (e.g. dimethyl sulfoxide);
propylene carbonate; and vegetable oil (e.g. soybean oil and cottonseed oil) .
[0076]
The gas carrier used herein includes, for example, fluorocarbon, butane gas, LPG (liquefied petroleum gas), dimethyl ether and carbon dioxide gas.
[0077]
The surfactant used herein includes, for example, a non-ionic surfactant such as polyoxyethylene alkyl ether, polyoxyethylene alkyl aryl ether, and polyethylene glycol fatty acid ester; and an anionic surfactant such as alkyl sulfonate, alkylbenzene sulfonate, and alkyl sulfate.
[0078]
The other formulation additives used herein include, fixing agents, dispersing agents, colorants, stabilizers, and the like; 1 and more specifically, casein, gelatin, saccharides (e.g. starch, gum arabic, cellulose derivatives, and alginic acid), lignin derivatives, bentonite, synthetic water-soluble polymers (e.g. polyvinyl alcohols, polyvinyl pyrrolidones , and polyacrylic acids) , PAP (acidic isopropyl phosphate) , , BHT (2 , 6-di-tert-butyl-4-methylphenol ) , BHA (a mixture of 2-tert-butyl-4-methoxyphenol and 3-tert-butyl-4- methoxyphenol) , and the like.
[0079]
The method for controlling harmaful arthropods in the present invention is performed by applying an effective amount of the present compound to harmaful arthropods directly and/or habitats of harmaful arthropods, (e.g. plant body, soil, indoor, and animal body) . According to the method for controlling harmaful arthropods in the present invention, the present compound is generally used in the form of a harmaful arthropod control agent of the present invention .
[0080]
The habitats of harmaful arthropods include, for example, paddy fields, farms, orchards, non-crop lands, and houses.
In the control method, the present compound can be applied to arthropod pests or areas where arthropod pests live by allowing the compound to come into contact with the arthropod pests or causing the arthropod pests to ingest the compound, according to the same method as in the case of conventional arthropod pest control agents.
Examples of such application method include a spraying treatment, a soil treatment, a seed treatment, and a water culture medium treatment.
[0081] When the harmaful arthropod control agent of the present invention is used for controlling pests in the field of agriculture, the application amount thereof is 1 g to 10, 000 g of the present compound per 10, 000 m 2 . When the harmaful arthropod control agent of the present invention is formulated into, for example, emulsions, wettable powders, and flowable formulations, the pesticidal agent is generally diluted with water so that the active ingredient concentration thereof can be 0.01 ppm to 10,000 ppm. When the pesticidal agent is formulated into, for example, granules and powders, the pesticidal agent is generally used without dilution.
[0082]
These formulations and water dilutions thereof may be directly sprayed to harmaful arthropods or plants (e.g. crops which need to be protected from harmaful arthropods) , or may be applied to a soil of a cultivated land in order to control harmaful arthropods which inhabit the soil.
[0083]
The harmaful arthropod control agent of the present invention can also be used in the form of a resin preparation which may be, for example, processed into a sheet or a string, and then wound around crops, or put around crops, or laid on the soil surface near the root of crops. [0084]
The harmaful arthropod control agent of the present invention can be used for controlling pests which live in a house. When it is used at a plain surface, the application amount thereof is generally 0.01 mg to 1, 000 mg of the present compound per 1 m 2 of the treatment area; and when it is used in an open space, the application amount thereof is generally 0.01 mg to 500 mg of the present compound per 1 m 3 of the treatment space. When the pesticidal agent of the present invention is formulated into, for example, emulsions, wettable powders, and flowable formulations, the harmaful arthropod control agent is generally diluted with water so that the active ingredient concentration thereof can be 0.1 ppm to 1,000 ppm. When the pesticidal agent is formulated into, for example, oil solution, aerosol, smoking agent and toxic bait, the harmaful arthropod control agent is generally used without dilution.
[0085]
The harmaful arthropod control agent of the present invention can be used in farmlands where the following "crops" are cultivated.
Agricultural crops: Corn, rice, wheat, barley, rye, oat, sorghum, cotton, soybean, peanut, sarrazin, sugar beet, rapeseed, sunflower, sugar cane, tobacco, and the like.
Vegetables: Solanaceae vegetables (e.g. . eggplant, tomato, green pepper, hot pepper, and . potato) , Cucurbitaceae vegetables (e.g. cucumber, . pumpkin, zucchini, watermelon, and melon), Cruciferae vegetables (e.g. Japanese radish, turnip, horseradish, kohlrabi, Chinese cabbage, cabbage, brown mustard, broccoli, and cauliflower) , Compositae vegetables (e.g. burdock, garland chrysanthemum, artichoke, and lettuce), Liliaceae vegetables (e.g. Welsh onion, onion, garlic, and asparagus) , Umbelliferae vegetables (e.g. carrot, parsley, celery, and parsnip), Chenopodiaceae vegetables (e.g. spinach and Swiss chard), Labiatae vegetables (e.g. Japanese basil, mint, and basil), strawberry, sweat potato, yam, aroid, and the like.
Flowers.
Foliage plants.
Fruit trees: Pomaceous fruits (e.g. apple, common pear, Japanese pear, Chinese quince, and quince) , stone fleshy fruits (e.g. peach, plum, nectarine, Japanese plum, cherry, apricot, and prune), citrus plants (e.g. Satsuma mandarin, orange, lemon, lime, and grapefruit), nuts (e.g. chestnut, walnut, hazel nut, almond, pistachio, cashew nut, and macadamia nut), berry fruits (e.g. blueberry, cranberry, blackberry, and raspberry) , grape, persimmon, olive, loquat, banana, coffee, date, coconut, and the like.
Trees other than fruit trees: Tea, mulberry, flowering trees and street trees (e.g. ash tree, birch, dogwood, eucalyptus, ginkgo, lilac, maple tree, oak, poplar, cercis, Chinese sweet gum, plane tree, zelkova, Japanese arborvitae, fir tree, Japanese hemlock, needle juniper, pine, spruce, yew), and the like.
[0086]
The "crops" also include recombinant crops.
[0087]
The harmaful arthropod control agent of the present invention can be mixed or used together with other insecticides, acaricides, nematicides, fungicides, plant growth regulators, herbicides and/or synergists. Hereinafter, examples of the active ingredients of the above-mentioned insecticides, acaricides, nematicides, fungicides, plant growth regulators, herbicides and synergists are illustrated.
[0088]
Active ingredients of insecticides:
(1) Organic phosphorus compounds:
Acephate, Aluminium phosphide, butathiofos, cadusafo.s, chlorethoxyfos , chlorfenvinphos , chlorpyrifos , chlorpyrifos-methyl, cyanophos:, CYAP, DCIP (diazinon, dichlorodiisopropyl ether), , dichlofenthion : ECP, dichlorvos: DDVP, dimethoate, dimethylvinphos , disulfoton, EPN, ethion, ethoprophos, etrimfos, fenthion: MPP, fenitrothion : MEP, fosthiazate, formothion, Hydrogen phosphide, isofenphos, isoxathion, malathion, mesulfenfos , methidathion: DMTP, monocrotophos , naled: BRP, oxydeprofos: ESP, parathion, phosalone, phosmet: PMP, pirimiphos-methyl , pyridafenthion, quinalphos, phenthoate: PAP, profenofos, propaphos, prothiofos, pyraclorfos, salithion, . sulprofos, tebupirimfos, temephos, tetrachlorvinphos , terbufos, thiometon, trichlorphon : DEP, vamidothion, phorate, and cadusafos.
(2) Carbamate compounds:
Alanycarb, bendiocarb, benfuracarb, BPMC, carbaryl, carbofuran, carbosulfan, cloethocarb, ethiofencarb, fenobucarb, fenothiocarb, fenoxycarb, furathiocarb, isoprocarb: MIPC, metolcarb, methomyl, methiocarb, NAC, oxamyl, pirimicarb, propoxur: PHC, XMC, thiodicarb, xylylcarb, and aldicarb.
(3) Pyrethroid compounds:
Acrinathrin, allethrin, benfluthrin, beta-cyfluthrin, bifenthrin, cycloprothrin, cyfluthrin, cyhalothrin, cypermethrin, deltamethrin, esfenvalerate, ethofenprox, fenpropathrin, fenvalerate, flucythrinate, flufenoprox, flumethrin, fluvalinate, halfenprox, imiprothrin, permethrin, prallethrin, pyrethrins, resmethrin, sigma- cypermethrin, silafluofen, tefluthrin, tralomethrin, transfluthrin, tetramethrin, phenothrin, cyphenothrin, alpha-cypermethrin, zeta-cypermethrin, lambda-cyhalothrin, gamma-cyhalothrin, furamethrin, tau-fluvalinate, metofluthrin, 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 compounds:
Cartap, bensultap, thiocyclam, monosultap, and bisultap.
(5) Neonicotinoid compounds:
Imidacloprid, nitenpyram, acetamiprid, thiamethoxam, thiacloprid, dinotefuran, and clothianidin .
(6) Benzoylurea compounds:
Chlorfluazuron, bistrifluron, diafenthiuron, diflubenzuron, fluazuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron, triflumuron, and triazuron.
(7) Phenylpyrazole compounds:
Acetoprole, ethiprole, fipronil, vaniliprole, pyriprole, and pyrafluprole .
(8)Bt toxines:
Live spores derived from and crystal toxins produced from Bacillus thuringiesis and a mixture thereof; (9) Hydrazine compounds:
Chromafenozide, halofenozide, methoxyfenozide, and tebufenozide .
(10) Organic chlorine compounds:
Aaldrin, dieldrin, dienochlor, endosulfan, and methoxychlor .
(11) Other insecticidal active ingredients:
Mmachine oil, nicotine-sulfate; avermectin-B, bromopropylate, buprofezin, chlorphenapyr, cyantraniliprole, cyromazine, D-D ( 1 , 3-Dichloropropene ) , emamectin-benzoate, fenazaquin, flupyrazofos , hydroprene, methoprene, indoxacarb, metoxadiazone, milbemycin-A, pymetrozine, pyridalyl, pyriproxyfen, spinosad, sulfluramid, tolfenpyrad, triazamate, flubendiamide, lepimectin, arsenic acid, benclothiaz, calcium cyanamide, calcium polysulfide, chlordane, DDT, DSP, flufenerim, flonicamid, flurimfen, formetanate, metarn-ammonium, metam-sodium, Methyl bromide, Potassium oleate, protrifenbute, spiromesifen, sulfoxaflor, sulfur, metaflumizone, spirotetramat , pyrifluquinazone, spinetoram, chlorantraniliprole , tralopyril, cyantraniliprole,
[0089]
Active ingredients of acardides:
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 .
[0090]
Active ingredients of nematocides:
DCIP, fosthiazate, levamisole hydrochloride
(levamisole) , methyisothiocyanate, morantel tartarate, and imicyafos .
[0091]
Active ingredients of fungicides:
Azole fungicidal compounds such as propiconazole, prothioconazole, triadimenol, prochloraz, penconazole, tebuconazole, flusilazole, diniconazole, bromuconazole, epoxiconazole, difenoconazole, cyproconazole, metconazole, triflumizole, tetraconazole , myclobutanil , fenbuconazole , hexaconazole, fluquinconazole, triticonazole, . bitertanol, imazalil, and. flutriafol;
Cyclic amine fungicidal compouds such as fenpropimorph, tridemorph, and fenpropidin;
Benzimidazole fungicidal compounds such as carbendezim, benomyl, thiabendazole, and thiophanate-methyl ;
Procymidone; cyprodinil; pyrimethanil ; diethofencarb; thiuram; fluazinam; mancozeb; iprodione; vinclozolin; chlorothalonil ; captan; mepanipyrim; fenpiclonil; fludioxonil ; dichlofluanid; folpet; kresoxim-methyl ; azoxystrobin; trifloxystrobin; fluoxastrobin; picoxystrobin; pyraclostrobin; dimoxystrobin; pyribencarb; spiroxamine; quinoxyfen; fenhexamid; famoxadone; fenamidone; zoxamide; ethaboxam; amisulbrom; iprovalicarb; benthiavalicarb; cyazofamid; mandipropamid; boscalid; penthiopyrad; metrafenone; fluopiran; bixafen; cyflufenamid; proquinazid; isotianil, and tiadinil.
[0092]
Active ingredients of herbicides:
(1) Phenoxyfatty acid herbicidal compounds:
2,4-PA, MCP, MCPB, phenothiol, mecoprop, fluroxypyr, triclopyr, clomeprop, and naproanilide .
(2) .Benzoic acid herbicidal compounds:
2,3,6-TBA, dicamba, clopyralid, picloram, aminopyralid, quinclorac, and quinmerac.
(3) Urea herbicidal compounds:
Diuron, linuron, chlbrtoluron, isoproturon, fluometuron, isouron, tebuthiuron, methabenzthiazuron, cumyluron, daimuron, and methyl-daimuron . '
(4) Triazine herbicidal compounds:
Atrazine, ametoryn, cyanazine, simazine, propazine, simetryn, dimethametryn, prometryn, metribuzin, triaziflam, and indaziflam.
(5) Bipyridinium herbicidal compounds:
Paraquat and diquat.
(6) Hydroxybenzonitrile herbicidal compounds:
Bromoxynil and ioxynil.
(7) Dinitroaniline herbicidal compounds:
Pendimethalin, prodiamine, and trifluralin.
(8) Organic phosphorus herbicidal compounds,:
Amiprofos-methyl, butamifos, bensulide, piperophos, anilofos, glyphosate, glufosinate, glufosinate-P, and bialaphos .
(9) Carbamate herbicidal compounds:
Di-allate, tri-allate, EPTC, butylate, benthiocarb, esprocarb, molinate, dimepiperate, swep, chlorpropham, phenmedipham, phenisopham, pyributicarb, and asulam.
(10) Acid amide herbicidal compounds:
Propanil, propyzamide, bromobutide, and etobenzanid.
(11) Chloroacetanilide herbicidal compounds:
Acetochlor, alachlor, butachlor, dimethenamid, propachlor, metazachlor, metolachlor, pretilachlor , thenylchlor, and pethoxamid.
(12) Diphenylether herbicidal compounds:.
Acifluorfen-sodium, bifenox, oxyfluorfen, lactofen, fomesafen, chlomethoxynil, and aclonifen.
(13) Cyclic imide herbicidal compounds: Oxadiazon, cinidon-ethyl , carfentrazone-ethyl , surfentrazone, flumiclorac-pentyl, flumioxazin, pyraflufen- ethyl, oxadiargyl, pentoxazone , fluthiacet-methyl , butafenacil, benzfendizone, bencarbazone, and saflufenacil .
(14) Pyrazole herbicidal compounds:
Benzofenap, pyrazolate, pyrazoxyfen, topramezone, and pyrasulfotole .
(15) Triketone herbicidal compounds:
Isoxaflutole, benzobicyclon, sulcotrione, mesotrione, tembotrione, and tefuryltrione .
(16) Aryloxyphenoxypropionic acid herbicidal compounds:
Clodinafop-propargyl, cyhalofop-butyl , diclofop-methyl , fenoxaprop-ethyl, fluazifop-butyl , haloxyfop-methyl, quizalofop-ethyl, and metamifop.
(17) Trioneoxime herbicidal compounds:
Alloxydim-sodium, sethoxydim, butroxydim, clethodim, cloproxydim, cycloxydim, tepraloxydim, tralkoxydim, and profoxydim.
(18) Sulfonylurea herbicidal compounds:
Chlorsulfuron, sulfometuron-methyl , metsulfuron-methyl , chlorimuron-ethyl , tribenuron-methyl , triasulfuron, bensulfuron-methyl, thifensulfuron-methyl , pyrazosulfuron- ethyl, primisulfuron-methyl, nicosulfuron, amidosulfuron, cinosulfuron, imazosulf ron; rimsulfuron, halosulfuron- methyl, prosulfuron, ethametsulfuron-methyl , triflusulfuron-methyl , flazasulfuron, cyclosulfamuron, flupyrsulfuron, sulfosulfuron, azimsulfuron, ethoxysulfuron, oxasulfuron, iodosulfuron-methyl-sodium, forarasulfuron, mesosulfuron-methyl, trifloxysulfuron, tritosulfuron, orthosulfamuron, flucetosulfuron, and propyrisulfuron .
(19) Imidazolinone herbicidal compounds:
Imazamethabenz-methyl , imazamethapyr , imazamox, imazapyr, imazaquin, and imazethapyr.
(20) Sulfonamide herbicidal compounds:
Flumetsulam, metosulam, diclosulam, florasulam, cloransulam-methyl, penoxsulam, and pyroxsulam.
(21) Pyrimidinyloxybenzoic acid herbicidal compounds:
Pyrithiobac-sodium, bispyribac-sodium, pyriminobac- methyl, pyribenzoxim, pyriftalid, and pyrimisulfan .
(22) Other herbicidal compounds:
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. [0093]
Active ingredients of synergists:
Piperonyl butoxide, sesamex, sulfoxide, N- (2- ethylhexyl) -8, 9, 10-trinorborn-5-ene-2 , 3-dicarboxyimide (MGK 264), N-declyimidazole, WARF-antiresistant , TBPT, TPP, IBP, PSCP, methyl iodide (CH 3 I), t-phenylbutenone, diethylmaleate, DMC, FDMC, ETP, and ETN.
Examples
[0094]
The present invention is described in more detail by Production Examples, Formulation Examples, and Test Examples, but the present invention is not limited to these Examples. In these Examples, Et represents an ethyl group.
[0095]
First, Production Examples of the present compound are shown below.
[0096]
Production Example 1
To N,N-dimethylformamide (20 ml), (2E, 4E) -octa-2 , 4- dienoic acid (500 mg, 3.57 mmol) and ( tetrahydrofuran-2- yl) methylamine (542 mg, 5.36 mmol) were added. To the mixture, triethylamine (741 mg, 7.32 mmol) and (benzotriazol-l-yloxy) -tris (dimetylamino ) phosphonium hexafluorophosphate (1893 mg, 4.28 mmol) were added under ice-cooling successively, and stirred for 1 hour under ice- cooling, then for 12 hours at room temperature. To a mixture 20 ml of hydrochloric acid (5%) and 50 ml of ice water, the reaction liquid was poured and extracted with ethyl acetate 2 times. The combined ethyl acetate layer was washed with 50 ml of saturated aqueous sodium hydrogen carbonate and 50 ml of brine successively. The organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give 481 mg of (2E, 4E) -N- (tetrahydrofuran-2-ylmethyl) octa-2, 4-dienamide of the formula :
(hereinafter, referred to as The Present Compound (1)).
[0097]
The Present Compound (1)
X H NMR (CDC1 3 ) : δ ppm: 0.91 (t, 3H) , 1.44 (m, 2H) ,
1.57 (m, 1H) , 1.89 (m, 2H) , 1.96 (m, 1H) , 2.13 (m, 2H) ,
3.23 (m, 1H), 3.68 (m, 1H) , 3.75 (m, 1H) , 3.86 (m, 1H) , 3.98 (m, 1H) , .5.75 (d, 1H, J = 15.2 Hz), 5.84 (bs, 1H) ,
6.03-6.17 (m, 2H), 7.21 (dd, 1H)
[0098]
Production Example 2 Using 0.29 g of (2E, 4E) -nona-2, 4-dienoic acid instead of 0.50 g of (2E, 4E) -octa-2 , 4-dienoic acid, 0.30 g of (2E, 4E) -N- (tetrahydrofuran-2-ylmethyl) nona-2, 4-dienamide of the following formula (hereinafter, referred to as The Present Compound (2)) was obtained in the similar way as Production Example 1.
[0099]
The Present Compound (2)
XH NMR (CDC1 3 ) : δ ppm: 0.89 (t, 3H) , 1.29 (m, 3H) ,
1.41 (m, 1H), 1.55 (m, 1H) , 1.92 (m, 2H) , 1.95 (m, 1H) ,
2.16 (m, 2H) , 3.23 (m, 1H) , 3.67 (m, 1H) , 3.77 (m, 1H) ,3.84 (m, 1H) , 3.98 (m, 1H) , 5.75 (d, 1H, J = 15.2 Hz), 5.82
(bs, 1H) , 6.07-6.12 (m, 2H) , 7.21 (dd, 1H)
[0100]
Production Example 3
Using 0.32 g of (2E, 4E) -deca-2 , 4-dienoic acid instead of 0.50 g of (2E, 4E) -octa-2 , 4-dienoic acid, 0.26 g of (2E,
4E) -N- (tetrahydrofuran-2-ylmethyl ) deca-2, 4-dienamide of the following formula (hereinafter, referred to as The Present
Compound (3)) was obtained in the similar way as Production
Example 1.
[0101]
The Present Compound (3)
¾ NMR (CDC1 3 ) : δ ppm: 0.89 (t, 3H) , 1.29 (m, 4H) , 1.42 (m, 2H) , 1.57 (m, 1H) , 1.90 (m, 2H) , 1.97 (m, 1H) , 2.17 (m, 2H) , 3.24 (m, 1H) , 3.67 (m, 1H) , 3.77 (m, 1H) , 3.87 (m, 1H) , 3.98 (m, 1H) , 5.75 (d, 1H, J = 15.2 Hz), 5.82 (bs, 1H) , 6.05-6.16 (m, 2H) , 7.21 (dd, 1H)
[0102]
Production Example 4
Using 0.17 g of (2E, 4E) -dodeca-2 , 4-dienoic acid instead of 0.50 g of (2E, 4E) -octa-2 , -dienoic acid, 0.21 g of (2E, 4E) -N- (tetrahydrofuran-2-ylmethyl) dodeca-2, 4- dienamide of the following formula (hereinafter, referred to as The Present Compound (4)) was obtained in the similar way as Production Example 1.
[0103]
The Present Compound (4)
X H NMR (CDCI3) : δ ppm: 0.89 (t, 3H) , 1.28 (m, 6H) , 1.40 (m, 2H), 1.57 (m, 1H) , 1.90 (m, 2H) , 1.98 (m, 1H) , 2.16 (m, 2H) , 3.23 (m, 1H) , 3.67 (m, 1H) , 3.77 (m, 1H) , 3.87 (m, 1H) , 3.98 (m, 1H) , 5.75 (d, 1H, J = 15.2 Hz), 5.81 (bs, 1H) , 6.05-6.16 (m, 2H) , 7.21 (dd, 1H)
[0104]
Production Example 5
Under nitrogen atmosphere, to a mixture of 1.4 g of (tetrahydrofuran-3-yl)methylamine hydrochloride (Reference Production Example 3) and 20 ml of anhydrous tetrahydrofuran, 1.0 g of triethylamine was added at room temperature and : stirred for 30 minutes. To the mixed liquid, 0.63 g of (2E, 4E) -hepta-2 , 4-dienoic acid and 1.9 g of ■ l-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride were added, and stirred for 4 hours at room temperature. Then, to the reaction mixture, water was added and extracted with ethyl acetate 2 times. The organic layer was washed with brine, and dried over anhydrous sodium sulfate, then, concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give 0.75 g of (2E, 4E) -N- (tetrahydrofuran-3-ylmethyl) hepta-2, 4-dienamide of the formula :
(hereinafter, referred to as The Present Compound (5)).
( 5 )
[0105]
The Present Compound (5)
1 H NMR (GDC1 3 ) : δ ppm: 7.24-7.16 (1H, m) , 6.15-6.10 (2H, m) , 5.74 (1H, d) , 5.61 (1H, brs), 3.89 (1H, td) , 3.81 (1H, dd) , 3.74 (1H, q) , 3.55 (1H, dd) , 3.42-3.31 (2H, m) , 2.57-2.47 (1H, m) , 2.22-2.14 (2H, m) , 2.09-1.99 (1H, m) , 1.67-1.57 (1H, m) , 1.03 (3H, t)
[0106]
Production Example 6
Using 0.42 g of (2E, 4E) -octa-2 , 4-dienoic acid instead of 0.63 g of (2E, 4E) -hepta-2 , 4-dienoic acid, 0.22 g of (2E, 4E) -N- (tetrahydrofuran-3-ylmethyl) octa-2, -dienamide of the following formula (hereinafter, referred to as The Present Compound (6)) was obtained in the similar way as Production Example 5.
[0107]
The Present Compound (6)
X H NMR (CDCI3) : δ ppm: 7.20 (1H, dd) , 6.17-6.04 (2H, m) , 5.74 1H, d) , 5.60 (1H, brs), 3.89 (1H, td) , 3.81 (1H, dd) , 3.73 (1H, dd) , 3.55 (1H, dd)., 3.41-3.30 (2H, m) , 2.57- 2.47 (1H, m) , 2.18-1.99 (3H, m) , 1.68-1.55 (1H, m) , 1.45 (2H, td) , 0.91 (3H, t) [0108]
Production Example 7
Using 0.62 g of (2E, 4E) -nona-2 , 4-dienoic acid instead of 0.63 g of (2E, 4E) -hepta-2 , 4-dienoic acid, 0.65 g of (2E, 4E) -N- (tetrahydrofuran-3-ylmethyl) nona-2, 4-dienamide of the following formula (hereinafter, referred to as The Present Compound (7)) was obtained in the similar way as Production Example 5.
[0109]
The Present Compound (7)
X H NMR (CDC1 3 ) : δ ppm: 7.20 (1H, dd) , 6.17-6.04 (2H, m) , 5.74 (1H, d), 5.66 (1H, brs) , 3.89 (1H, td) , 3.81 (1H, dd) , 3.74 (1H, dd) , 3.55 (1H, dd) , 3.41-3.30 (2H, m) , 2.57- 2.46 (1H, m) , 2.16 (2H, q) , 2.09-2.00 (1H, m) , 1.68-1.59
(1H, m) , 1.44-1.26 (4H, m) , 0.91 (3H, t)
[0110]
Production Example 8
Using 0.67 g of (2E, 4E) -deca-2 , 4-dienoic acid instead of 0.63 g of (2E, 4E) -hepta-2 , 4-dienoic acid, 0.55 g of (2E, 4E) -N- (tetrahydrofuran-3-ylmethyl) deca-2, 4-dienamide of the following formula (hereinafter, referred to as The Present Compound (8)) was obtained in the similar way as Production Example 5.
[0111]
The Present Compound (8)
Χ Η NMR (CDC1 3 ) : δ ppm: 7.20 (1H, dd) , 6.16-6.04 (2H, m) , 5.74 (1H, d) , 5.63 (1H, brs) , 3.89 (1H, td) , 3.81 (1H, dd) , 3.73 (1H, dd) , 3.55 (1H, dd) , 3.41-3.31 (2H, m) , 2.57- 2.47 (1H, m) , 2.15 (2H, dd) , 2.09-2.00 (1H, m) , 1.67-1.59
(1H, m) , 1.46-1.38 (2H, m) , 1.35-1.23 (4H, m) , 0.89. (3H, t)
[0112]
Production Example 9
Using 0.32 g of (2E, 4E) -dodeca-2 , 4-dienoic acid instead of 0.50 g of (2E, 4E) -octa-2 , 4-dienoic acid, and 0.29 g of (tetrahydrofuran-3-yl)methylamine instead of 0.54 g of (tetrahydrofuran-2-yl) methylamine, 0.26 g of (2E, 4E)- N- (tetrahydrofuran-3-ylmethyl ) dodeca-2, 4-dienamide of the following formula (hereinafter, referred to as The Present Compound (9)) was obtained in the similar way as Production Example 1.
[0113]
The Present Compound (9) X H NMR (CDCI3) : δ ppm: 0.88 (t, . 3H) , 1.28 (m, 6H.) , 1.40 (m, 2H) , 1.65 (m, 1H) , 2.03 (m, 1H) , 2.15 (m, 2H) , 2.51 (m, 1H) , 3.37 (m, 2H) , 3.56 (m, 1H) , 3.75 (m, 1H) , 3.81 (m, 1H) , 3.88 (m, 1H) , 5.61 (bs, 1H) , 5.73 (d, 1H, J = 15.2 Hz), 6.04-6.16 (m, 2H) , 7.21 (dd, 1H)
[0114]
Production Example 10
To 20 ml of dichloromethane, (2E, 4E) -N- (2, 2-dimethyl- 1, 3-dioxolan-4-ylmethyl) nona-2, 4-dienamide (1737 mg, 6.51 mmol, Production Example 25) was added, and to the mixture, dimethoxymethane (1.0 g, 13.2 mmol) and phosphorus pentoxide (1.0 g, 7.00 mmol) were added successively, then, the mixture was stirred for 1 hour under ice-cooling and for 96 hours at room temperature. To the reaction liquid, 12 ml of 5 % of aqueous sodium hydroxide solution, 20 ml of ice-water and 40 ml of ethyl acetate were added, and stirred for 1 hour at room temperature. The reaction mixture was extracted with dichlorometane, and obtained aqueous layer was extracted with 50 ml of ethyl acetate. Obtained dichloromethane layer and ethyl acetate layer were collectively washed with 50 ml of brine 2 times, and dried over magnesium sulfate, then concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give 120 mg of (2E, 4E) -N- ( 1 , 3-dioxolan- 4-ylmethyl) nona-2, 4-dienamide of the formula: (hereinafter, referred to as The Present Compound (10)).
[0115]
The Present Compound (10)
XH . NMR (CDC1 3 ) : δ ppm: 0.91 (t, 3H) , 1.30-1.43 (m, 4H) ,
2.16 (m, 2H) , 3.42 (m, 1H) , 3.60-3.70 (m, 2H) , 3.95 (m, 1H) , 4.18 (m, 1H) , 4.84 (s, 1H) , 5.06 (s, 1H) , 5.76 (d, 1H) , 5.78 (bs, 1H) , 6.07-6.17 (m, 2H) , 7.22 (dd, 1H)
[0116]
Production Example 11
To 15 ml of dichloromethane, (2E,'4E)-N-(2, 2-dimethyl- 1 , 3-dioxolane-4-ylmethyl ) deca-2 , 4-dienamide (1377 mg, 4.90 mmol, Production Example 26) was added, and to the mixture, dimethoxymethane (0.75 g, 9.87 mmol) and phosphorus pentoxide (1.0 g, 7.00 mmol) were added successively, then, the mixture was stirred for 1 hour under ice-cooling and for 96 hours at room temperature. To the reaction liquid, 40 ml of 2.5 % of aqueous sodium hydroxide solution, 20 ml of ice-water and 40 ml of ethyl acetate were added, then stirred for 1 hour at room temperature. The reaction, mixture was extracted with dichlorometane, and obtained aqueous layer was extracted with 50 ml of ethyl acetate. Obtained dichloromethane layer and ethyl acetate layer were collectively washed with 50 ml of brine 2 times, and dried over magnesium sulfate, then concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give 80 mg of (2E, 4E) -N- (1, 3-dioxolan-4- ylmethyl ) deca-2 , 4-dienamide of the formula:
(hereinafter, referred to as The Present Compound (11) ) .
[0117]
The Present Compound (11)
X H NMR (CDCI3) : δ ppm: 0.89 (t, 3H) , 1.27-1.44 (m, 6H) , 2.16 (m, 2H) , 3.42 (m, 1H) , 3.60-3.70 (m, 2H) , 3.95 (m, 1H) , 4.20 (m, 1H), 4.84 (s, 1H) , 5.06 (s, 1H) , 5.76 (d, 1H) , 5.78 (bs, 1H) , 6.09-6.17 (m, 2H) , 7.21 (dd, 1H)
[0118]
Prodution Example 12
Using 0.91 g of (2E, 4E) -nona-2 , 4-dienoic acid instead of 0.63 g of (2E, 4E) -hepta-2 , 4-dienoic acid, and 0.81 g of
( 3-methyloxetan-3-yl ) methylamine hydrochloride (Reference Production Example 6) instead of 1.4 g of ( tetrahydrofuran- 3-yl) methylamine hydrochloride, 0.31 g of (2E, 4E)-N-(3- methyloxetan-3-ylmethyl) nona-2, 4-dienamide of the following formula (hereinafter, referred to as The Present Compound
(12)) was obtained in the similar way as Production Example 5.
[0119]
The Present Compound (12)
1 H NMR (CDC1 3 ) : δ ppm: 7.23 (1H, dd) , 6.16-6.12 (2H, m) , 5.82 (1H, brs) , 5.77 (1H, d) , 4.39 (1H, t), 3.53-3.23
(5H, m) , 2.21-2.15 (2H, " m), 1.45-1.22 (4H, m) , 0.97 (3H, s), 0.91 (3H, t).
[0120]
Prodution Example 13
Using 0.42 g of (2E, 4E) -octa-2 , 4-dienoic acid instead of 0.63 g of (2E, 4E) -hepta-2 , 4-dienoic acid, and 0.51 g of ( tetrahydropyran-4-yl ) methylamine instead of 1.4 g of (tetrahydrofuran-3-yl) methylamine hydrochloride, 0.12 g of (2E, 4E) -N- ( tetrahydropyran-4-ylmethyl ) octa-2, 4-dienamide of the following formula (hereinafter, referred to as The
Present Compound (13)) was obtained in the similar way as
Production Example 5.
[0121]
The Present Compound X H NMR (CDCI 3 ) : δ ppm: 7.20 (1H, dd) , 6.17-6.04 (2H, m), . 5.74 (1H, d) , 5.54 (1H, brs) , 3.97 (2H, dd) , 3.36 (2H, td) , 3.24 (2H, t), 2.13 (2H, q) , 1.85-1.74 (1H, m) , 1.65-
1.55 (2H, m) , 1.50-1.40 (2H, m) , 1.38-1.27 (2H, m) , 0.91 (3H, t).
[0122]
Prodution Example 14
Using 0.46 g of (2E, 4E) -nona-2 , 4-dienoic acid instead of 0.63 g of (2E, 4E) -hepta-2 , 4-dienoic acid, and 0.51 g of (tetrahydropyran-4-yl) methylamine instead of 1.4 g of (tetrahydrofuran-3-yl) methylamine hydrochloride, 0.41 g of (2E, 4E) -N- (tetrahydropyran-4-ylmethyl) nona-2, 4-dienamide of the following formula (hereinafter, referred to as The Present Compound (14)) was obtained in the similar way as Production Example 5.
[0123]
The Present Compound (14)
1 H NMR (CDCI 3 ) : δ ppm: 7.20 (1H, dd) , 6.16-6.04 (2H, m) , 5.73 (1H, d) , 5.52 (1H, brs), 3.97 (2H, dd) , 3.36 (2H, td) , 3.24 (2H, t), 2.15 (2H, q) , 1.85-1.74 (1H, m) , 1.65- 1.55 (2H, m) , 1.44-1.27 (6H, m) , 0.90 (3H, t).
[0124] Prodution Example 15
Using 52 mg of (2E, 4E) -nona-2 , 4 , 8-trienoic acid (Reference Production Example 7) instead of 0.50 g of (2E, 4E) -octa-2, 4-dienoic acid, 39 mg of (2E, , 4E)-N- (tetrahydrofuran-2-ylmethyl ) nona-2 , 4 , 8-trienamide of the following formula (hereinafter, referred to as The Present Compound (15)) was obtained in the similar way as Production Example 1.
[0125]
The Present Compound (15)
1 H NMR (CDC1 3 ) : δ ppm: 1.56 (m, 1H) , 1.88-2.00 (m, 3H) , 2.19 (m, 2H) , 2.24 (m, 2H) , 3.23 (m, 1H) , 3.65 (m, 1H) , 3.73 (m, 1H), 3.85 (m, 1H) , 3.98 (m, 1H) , 5.03 (m, 2H) , 5.75-5.85 (m, 3H) , 6.06-6.16 (m, 2H) , 7.19 (dd, 1H)
[0126]
Prodution Example 16
Using 0.47 g of (2E, 4E) -nona-2 , 4 , 8-trienoic acid (Reference Production Example 7) instead of 0.50 mg of (2E, 4E) -octa-2 , 4-dienoic acid, and 0.60 g of (tetrahydrofuran- 3-yl) methylamine instead of 0.54 g of (tetrahydrofuran-2- yl)methylamine, 0.44 g of (2E, 4E) -N- (tetrahydrofuran-3- ylmethyl) nona-2, , 8-trienamide of ' the following formula (hereinafter> referred to as The Present Compound (16)) was obtained in the similar way as Production Example 1.
[0127]
The Present Compound (16)
X H NMR (CDC1 3 ) : δ ppm: 1.64 (m, 1H) , 2.06 (m, 1H) , 2.22 (m, 2H), 2.26 (m, 2H) , 2.50 (m, 1H) , 3.37· (m, 2H) , 3.56 (m, 1H) , 3.73 (m, 1H) , 3.82 (m, 1H) , 3.89 (m, 1H) , 5.05 (m, 2H) , 5.61 (bs, 1H) , 5.73-6.15 (m, 4H) , 7.21 (dd, 1H)
[0128]
Prodution Example 17
Using 76 mg of (2E, 4E) -deca-2 , 4-dien-9-ynoic acid (Reference Production Example 8) instead of 0.50 g of (2E, 4E) -octa-2, ' 4-dienoic acid, 71 mg of (2E, 4E)-N- (tetrahydrofuran-2-ylmethyl ) deca-2, 4-dien-9-ynamide of the following formula (hereinafter, referred to as The Present Compound (17)) was obtained in the similar way as Production Example 1.
[0129]
The Present Compound (17)
Η NMR (CDCI3) : δ ppm: 1.54-1.69 (m, 3H) , 1.86-2.01 (m, 4H) , 2.21-2.31 (m, 4H) , 3.20-3.25 (m, 1H) , 3.69 (m, 1H) , 3.77 (m, 1H) , 3.87 (m, 1H) , 3.98 (m, 1H) , 5.78 (d, 1H, J = 15.2 Hz), 5.91 (bs, lH) , 6.04-6.21 (m, 2H) , 7.21 (dd, 1H)
[0130] '
Prodution Example 18
Using 0.30 g of (2E, 4E) -deca-2 , 4 , 9-trienoic acid (Reference Production Example 9) instead of 0.50 g of (2E, 4E) -octa-2, 4-dienoic acid, 0.16 g of (2E, 4E)-N- (tetrahydrofuran-2-ylmethyl ) deca-2 , 4 , 9-trienamide of the following formula (hereinafter, referred to as The Present Compound (18)) was obtained in the similar way as Production Example 1.
[0131]
The Present Compound (18)
X H NMR (CDC1 3 ) : δ ppm: 1.54-1.58 (m, 3H) , 1.88-1.9.3 (m, 2H) , 1.98 (m, 1H) , 2.06 (m, 2H) , 2.18 (m, 2H) , 3.23 (m, 1H) , 3.65 (m, 1H), 3.76 (m, l ' H) , 3.87. (m, 1H) , 3.98 (m, 1H) , 4.98-5.03 (m, 2H) , 5.74-5.84 (m, 3H) , 6.06-6.13 (m, 2H) , 7.20 (dd, 1H)
[0132]
Prodution Example 19
Using 0.51 g of (2E, 4E) -6-butyloxyhexa-2 , 4-dienoic acid (Reference Production Example 10) instead of 0.50 g of (2E, 4E) -octa-2, 4-dienoic acid, 0.49 g of (2E, 4E)-N- (tetrahydrofuran-2-ylmethyl) -6-butyloxyhexa-2 , 4-dienamide of the following formula (hereinafter, referred to as The Present Compound (19)) was obtained in the similar way as
Production Example 1.
[0133]
The Present Compound (19)
X H NMR (CDC1 3 ) : δ ppm: 0.91 (t, 3H) , 1.28 (m, 2H) , 1.40 (m, 2H) , 1.57 (m, 2H) , 1.94 (m, 2H) , 1.99 (m, 1H) , 3.24 (m, 1H) , 3.45 (m, 2H) , 3.67 (m, 1H) , 3.77 (m, 1H) , 3.87 (m, 1H) , 3.99 (m, 1H) , 4.06 (m, 1H) , 5.85 (d, 1H, J .= 15.2 Hz), 5.87 (bs, 1H) , 6.10 (dt, 1H) , 6.32 (m, 1H) , 7.24 (dd, 1H)
[0134]
Production Example 20
To N,N-dimethylformamide (15 · ml), (2EZ, 4E) -3- methylnona-2, 4-dienoic acid ( (2E, 4E) form : (2Z, 4E) form = 2 : 1) (882 mg, 5.25 mmol) and (tetrahydrofuran-2- yl) methylamine (690 mg, 6.83 mmol) were added, then, to the mixture, (benzotriazol-l-yloxy) - tris (dimethylamino) phosphonium hexafluorophosphate (3.00 g, 6.78 mmol) was added gradually under ice-cooling and stirred forJ 1 hour under ice-cooling and for 12 hours at room temperature. To the reaction liquid, 20 ml of 5% hydrochloric acid and 50 ml of saturated aqueous sodium hydrogen carbonate solution were added, and extacted with 100 ml of ethyl acetate 2 times. The ethyl acetate layers were washed collectively with 50 ml of ice-water and 50 ml of brine successively. The organic layer was dried over magnesium sulfate, then concentrated under reduced pressure The residue was purified by silica gel column chromatography to give 0.39 g of (2E, 4E) -N- (tetrahydrofuran-2-ylmethyl) -3-methylnona-2 , 4-dienamide of the following formula (hereinafter, referred to as The Present Compound (20)) as higher polarly fraction.
[0135]
The Present Compound (20)
X H NMR (CDC1 3 ) : δ ppm: 0.90 (t, 3H) , 1.30-1.42 (m, 4H) , 1.55 (m, 1H) , 1.88-2.00 · (m, 3H) , 2.16 (m, 2H) , 2.26 (s, 3H) , 3.20 (m, 1H) , 3.61 (m, 1H) , . 3.76 (m, 1H) , 3.84 (m, 1H) , 3.97 (m, 1H) , 5.59 (s, 1H) , 5.80 (bs, 1H) , 6.02-6.04 (m, 2H) [0136]
Production Example 21
Using 0.44 g of (2EZ, 4E) -3-methyldeca-2 , 4-dienoic acid ( (2E, 4E) form : (2Z, 4E) form = 2 : 1) instead of 0.88 g of ( 2EZ , 4E) -3-methylnona-2 , 4-dienoic acid ( (2E, 4E) form : (2Z, 4E) form = 2 : 1), 0.19 g of (2E, 4E)-N- (tetrahydrofuran-2-ylmethyl) -3-methyldeca-2 , -dienamide of the following formula (hereinafter, referred to as The Present Compound (21)) was obtained in the similar way as Production Example 20.
[0137]
The Present Compound (21)
X H NMR (CDC1 3 ) : δ ppm: 0.89 (t, 3Η)·, 1.29-1.61 (m, 7H) , 1.88-2.00 (m, 3H) , 2.13 (m, 2H) , 2.26 (s, 3H) , 3.20 (m, 1H) , 3.62 (m, 1H) , 3.76 (m, 1H) , 3.86 (m, .1H) , 3.97 (m, 1H) , 5.59 (s, 1H) , 5.80 (bs, 1H) , 6.02-6.04 (m, 2H)
[0138]
Production Example 22
Using 0.42 g of (tetrahydrofuran-3-yl) methylamine instead of 0.69 g of ( tetrahydrofuran-2-yl ) methylamine, 0.16 g of(2E, . 4E) -N- (tetrahydrofuran-3-ylmethyl) -3- methylnona-2 , 4-dienamide of the following formula (hereinafter, referred to as The Present Compound (22)) was obtained in the similar way as Production Example 20. [0139]
The Present Compound (22)
X H NMR (CDC1 3 ) : δ ppm: 0.91 (t, 3H) , 1.26-1.43 (m, 4H) , 1.64 (m, 1H) , 2.03 (m, 1H) , 2.14 (m, 2H) , 2.26 (s, 3H) , 2.51 (m, 1H), 3.34 (m, 2H) , 3.55 (m, 1H) , 3.75 (m, 1H) , 3.82 (m, 1H) , 3.88 (m, 1H) , 5.57 (s, 1H) , 5.58 (bs, 1H) , 6.03-6.05 (m, 2H)
[0140]
Production Example 23
Using 0.40 g of (2EZ, 4E) -3-methyldeca-2 , 4-dienoic acid ( (2E, 4E) form : (2Z, 4E) form = 2 : 1) instead of 0.88 g of (2EZ, 4E) -3-methylnona-2, 4-dienoic acid ( (2E, 4E) form : (2Z, 4E) form = 2 : 1), and 0.25 g of (tetrahydrofuran-3-yl ) methylamine instead of 0.69 g of (tetrahydrofuran-2-yl) methylamine, 0.11 g of (2E, 4E)-N- (tetrahydrofuran-3-ylmethyl) -3-methyldeca-2, 4-dienamide of the following formula (hereinafter, referred to as The Present Compound (23) ) was obtained in the similar way as Production Example 20.
[0141]
The Present Compound (23)
X H NMR (CDC1 3 ) : δ ppm: 0.89 (t, 3H) , 1.28-1.44 (m, 6H) , 1.64 (m, 1H) , 2.12 (m, 1H) , 2.15 (m, 2H) , 2.26 (s, 3H) , 2.51 (m, 1H) , 3.32 (m, 2H) , 3.55 (m, 1H) , 3.75 (m, 1H) , 3.82 (m, 1H), 3.88 (m, 1H) , 5.58 (s, 1H) , 5.68 (bs, 1H) , 6.03~6.05 (m, 2H)
[0142]
Production Example 24
Using 1.3 g of 4-tetrahydropyranylmethylamine instead of 0.69 g of (tetrahydrofuran-2-yl) methylamine, 0.35 g of (2E, 4E) -N- (4-tetrahydropyranylmethyl) -3-methylnona-2 , 4- dienamide of the following formula (hereinafter, referred to as The Present Compound (24)) was obtained in the similar way as Production Example 20.
[0143]
The Present Compound (24)
1 H NMR (CDC1 3 ) : δ ppm: 0.91 (t, 3H) , 1.30-1.42 (m, 6H) , 1.64 (m, 2H) , 1.78 (m, 1H) , 2.16 (m, 2H) , 2.26 (s, 3H) , 3.20 (m, 2H) , 3.36 (m, 2H) , 3.97 (m, 2H) , 5.55 (bs, 1H) , 5.57 (s, 1H) , 6.03-6.05 (m, 2H)
[0144]
Production Example 25
Using 1.9 g of (2E, 4E) -nona-2, 4-dienoic acid instead of 0.50g of (2E, 4E) -octa-2 , 4-dienoic acid, and 1.8 g of 2, 2-dimethyl-l, 3-dioxolan-4-yl ) methylamine instead of 0.54 g of (tetrahydrofuran-2-yl ) methylamine, 1.4 g of (2E, 4E)- N- (2, 2-dimethyl-l, 3-dioxolan-4-ylmethyl ) nona-2, 4-dienamide of the following formula (hereinafter, referred to as The Present Compound (25) ) was obtained in the similar way as Production Example 1.
[0145]
The Present Compound (25)
X H NMR (CDC1 3 ) : δ ppm: 0.91 (t, 3H) , 1.24-1.44 (m, 4H) , 1.35 (s, 3H) , 1.43 (s, 3H) , 2.16 (m, 2H) , 3.37 (m, 1H) , 3.62-3.66 (m, 2H) , 4.06 (m, 1H) , 4.26 (m, 1H) , 5.76 (d, 1H) , 5.78 (bs, 1H) , 6.08-6.13 (m, 2H) , 7.20 (dd, 1H)
[0146]
Production Exampple 26
Using 0.70 g of (2E, 4E) -deca-2 , 4-dienoic acid instead of 0.50 g of (2E, 4E) -octa-2 , 4-dienoic acid, and 0.71 g of 2 , 2-dimethyl-l , 3-dioxolan-4-yl ) methylamine instead of 0.54 g of (tetrahydrofuran-2-yl) methylamine, 0.44 g of (2E, 4E) - N- (2, 2-dimethyl-l, 3-dioxolan-4-ylmethyl) deca-2 ,,4-dienamide of the following formula (hereinafter, referred to as The Present Compound (26)) was obtained in the similar way as Production Example 1. -
[0147]
The Present Compound (26)
X H NMR (CDC1 3 ) : δ ppm: 0.89 (t, 3H) , 1.24-1.44 (m, 6H) , 1.35 (s, 3H) , 1.44 (s, 3H) , 2.16 (m, 2H) , 3.37 (m, 1H) , 3.63-3.66 (m, 2H) , 4.06 (m, 1H) , 4.26 (m, 1H) , 5.76 (d, 1H) , 5.83 (bs, 1H), 6.05-6.15 (m, 2H) , 7.20 (dd, 1H)
Production Example 27
Using 0.50 g of (2E, 4E) -7-methylocta-2 , -dienoic acid instead of 0.63 g of (2E, 4E) -hepta-2 , 4-dienoic acid, 0.32 g of (2E, 4E) -N- (tetrahydrofuran-3-ylmethyl) -7-methylocta- 2 , 4-dienamide of the following formula (hereinafter, ' referred to as The Present . Compound (27)) was obtained in the similar way as Production Example 5.
The Present. Compound (27) X H NMR (CDCI3) : δ ppm: 0.90 (6H, d) , 1.55-1.75 (2H, m) , 2.00-2.09 (3H, m) , 2.47-2.57 (1H, m) , 3.36 (2H, dt) , 3.56 (1H, dd) , 3.74 (1H, dd) , 3.81 (1H, dd) , 3.89 (1H, td) , 5.59 (1H, s), 5.74 (1H, d) , 6.03-6.16 (2H, m) , 7.21 (1H, dd) .
Production Example 28
Using 0.50 g of (2E, 4E) -7-methylocta-2, 4-dienoic acid instead of 0.63 g of (2E, 4E) -hepta-2 , 4-dienoic acid, and 0.43 g of (tetrahydropyran-4-yl ) methylamine instead of 0.54 g of (tetrahydrofuran-3-yl) methylamine hydrochloride, 0.28 g of (2Έ, 4E) -N- (tetrahydropyran-4-ylmethyl) -7-methylocta- 2 , 4-dienamide of the following formula (hereinafter, referred to as The Present Compound (28)) was obtained in the similar way as Production Example 5.
The Present Compound (28)
X H NMR (CDCI3) : δ ppm: 0.90 (6H, d) , 1.33 (2H, dq) , 1.56-1.65 (2H, m) , 1.66-1.74 (1H, m) , 1.74-1.85 (1H, m) , 2.04 (2H, t), 3.24 (-2H, t) , 3.37 (2H, dt) , 3.97 (2H, dd) , 5.53 (1H, s), 5.74 (1H, d) , 6.02-6.16 (2H, m) ., 7.21 (1H, dd)
Production Example 29 Using 0.25 g of (2E, 4E) -3-methylnona-2 , 4-dienoic acid (Reference Production Example 11) instead of 0.63 g of (2E, 4E ) -hepta-2 , -dienoic acid, and 0.26 g of (tetrahydropyran- 2-yl ) methylamine instead of 0.54 g of (tetrahydrofuran-3- " yl) methylamine hydrochloride, 0.28 g of (2E, 4E)-N- (tetrahydropyran-2-ylmethyl ) -3-methylnona-2 , 4-dienamide of the following formula (hereinafter, referred to as The Present Compound (29) ) was obtained in the similar way as Production Example 5.
The Present Compound (29)
½ NMR (CDC1 3 ) : δ ppm: 0.90 (3H, t) , 1.24-1.65 (9H, m) , 1.80-1.87 (1H, m) , 2.15 (2H, dq) , 2.26 (3H, d) , 3.02-3.09 (1H, m) , 3.36-3.45 (2H, m) , 3.62 (1H, ddd) , 3.92-4.00 (1H, m) , 5.60 (1H, s) , 5.89 (1H, s), 6.01-6.04 (2H, m)
Production Example 30
Using 0.23 g of (2E, 4E) -nona-2, -dienoic acid instead of 0.63 g of (2E, 4E) -hepta-2 , 4-dienoic acid, and 0.26 g of (tetrahydropyran-2-yl ) methylamine instead of 0..54 g of (tetrahydrofuran-3-yl) methylamine hydrochloride, 0.32 g of (2E, 4E) -N- (tetrahydropyran-2-ylmethyl) nona-2, -dienamide of the following formula (hereinafter, referred to as The Present Compound (30) ) was obtained in the similar way as Production Example 5.
The Present Compound (30)
X H NMR (CDC1 3 ) : δ ppm: 0.90 (3H, t), 1.24-1.63 (9H, m) , 1.79-1.88 (1H, m) , 2.15 (2H, q ) , 3.06-3.12 (lH, ' m), 3.38- 3.45 (2H, m) , 3.65 (1H, ddd) , 3.93-4.00 (1H, m) , 5.76 (1H, d) , 5.88 (1H, s), 6.02-6.17 (2H, m) , 7.19 (1H, dd)
Production Example 31
Under nitrogen atmosphere, a mixture of 1- ( tetrahydrofuran-3-yl ) ethylamine and anhydrous tetrahydrofuran was cooled under ice-bath, then, to the mixture, 0.67 g of (2E, 4E ) -nona-2 , 4-dienoyl chloride was dropwised. After dropwise, the mixture was taken from ice- bath and stirred for 2 hours. The reaction mixture was filtered, then, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give 0.21 g of (2E, 4E)-N-[1- ( tetrahydrofuran-3-yl) ethyl] nona-2, 4-dienamide of the following formula (hereinafter, referred to as The Present Compound (31) ) .
The Present Compound (31)
X H N R (CDC1 3 ) : δ ρριη: 0.90 (3H, t), 1.18 (3H, dd) , 1.28-1.44 (4H, m) , 1.70 (1H, tt), 2.00 (1H, dt) , 2.15 (2H, q) , 2.26-2.34 (1H, m) , 3.48 (0.5H, t) , 3.66-3.80 (2. OH, m) , 3.84-3.92 (1.5H, m) , 4.06-4.17 (1H, m) , 5.32 (0.5H, br s), 5.46 (0.5H, br s), 5.71 (1H, dd) , 6.06-6.16 (2H, m) , 7.14- 7.22 (lH,m)
Production Example 32
Using 0.60 g of (2E, 4E) -3-methylnona-2 , 4-dienoic acid (Reference Production Example 11) instead of 0.63 g of (2E, 4E) -hepta-2 , 4-dienoic acid, and 0.50 g of ( 1 , 3-dioxan-5- yl) methylamine instead of 0.54 g of (tetrahydrofuran-3- yl)methylamine hydrochloride, 0.52 g of (2E, 4E)-N-(1,3- dioxan-5-ylmethyl ) -3-methylnona-2 , 4-dienamide of the following formula (hereinafter, referred to as The Present Compound (32)) was obtained in the similar way as Production Example 5.
The Present Compound (32) 1 R NMR (CDCI 3 ) : δ ppm: 0.91 (3H, t) , 1.29-1.44 (4H, m) , 2.00-2.09 (1H, m) , 2.13-2.18 (2H, m) , 2.26 (3H, d) , 3.42 (2H, t), 3.73 (2H, dd) , 3.97 (2H, dd) , 4.83 (2H, dd) , 5.57 (1H, s), 5.70 (1H, s) , 6.00-6.10 (2H, m)
Production Example 33
Using 0.46 g of (2E, 4E) -nona-2 , 4-dienoic acid instead of 0.63 g of (2E, 4E) -hepta-2 , 4-dienoic acid, and 0.46 g of ( 1 , 3-dioxolan-2-yl ) methylamine instead of 0.54 g of (tetrahydrofuran-3-yl) methylamine hydrochloride, 0.48 g of (2E, 4E) -N- ( 1 , 3-dioxolan-2-ylmethyl ) nona-2 , 4-dienamide of the following formula (hereinafter, referred to as The Present Compound (33)) was obtained in the similar way as Production Example 5.
The Present Compound (33)
1 H NMR (CDCI 3 ) : δ ppm: 0.90 (3H, t) , 1.27-1.44 (4H, m) , 2.15 (2H, q) , 3.58 (2H, dd) , 3.86-4.03 (4H, m) , 4.98 (1H, t) , 5.67 (1H, s), 5.75 (1H, d) , 6.04-6.17 (2H, m) , 7,21 (1H, dd)
Production Example 34
Using 0.51 g of. (2E, 4E) -3-methylnona-2 , 4-dienoic acid (Reference Production Example 11) instead of 0.63 g of (2E, 4E) -hepta-2, 4-dienoic acid, and 0.46 g of ( 1 , 3-dioxan-2- yl) methylamine instead of 0.54 g of (tetrahydrofuran-3- yl)methylamine hydrochloride, 0.43 g of (2E, 4E)-N-(1,3- dioxolan-2-ylmethyl ) -3-methylnona-2 , 4-dienamide of the following formula (hereinafter, referred to as The Present Compound (34)) was obtained in the similar way as Production Example 5.
The Present Compound (34)
c
X H NMR . (CDCI3) : δ ppm: . 0.91 (3H, t) , 1.28-1.44 (4H, m) , 2.10-2.18 (2H, m) , 2.26 (3H, d) , 3.55 (2H, dd) , 3.86- 4.03 (4H, m) , 4.98 (1H, t) , 5.59 (1H, s) , 5.65 (1H, s) , 6.02-6.05 (2H, m)
Production Example 35
Using 0.34 g of (2E, 4E) -3-methylnona-2, 4-dienoic acid (Reference Production Example 11) instead of 0.63 g of (2E, 4E) -hepta-2 , 4-dienoic acid, and 0.25 g of ( 1 , 3-dioxolan-4- yl) methylamine instead of 0.54 g of (tetrahydrofuran-3- yl) methylamine hydrochloride, 0.44 g of (2E, 4E) -N- (1, 3- dioxolan-4-ylmethyl) -3-methylnona-2, 4-dienamide of the following formula (hereinafter, referred to as The Present Compound (35) ) was obtained in the similar way as Production Example 5.
The Present Compound (35)
X H NMR (CDC1 3 ) : δ ppm: 0.91 (3H, t), 1.29-1.45 (4H, m) , 2.14-2.19 (2H, m) , 2.28 (3H, d) , 3.88-3.97 (4H, m) , 4.01- 4.06 (1H, m) , 4.76 (1H, d) , 5.01 (1H, d) , 5.66 (1H, s) , 6.04-6.07 (2H, m) , 6.36 (1H, d)
Production Example 36
Using 0.34 g of (2E, 4E) -3-methylnona-2 ,.4-dienoic acid (Reference Production Example 11) instead of 0.63 g of (2E, 4E) -hepta-2 , 4-dienoic acid, and 0.28 g of ( 1 , 4-dioxan-2- yl) methylamine instead of 0.54 g of (tetrahydrofuran-3- yl)methylamine hydrochloride, 0.17 g of (2E, 4E)-N-(1,4- dioxan-2-ylmethyl) -3-methylnona-2, 4-dienamide of the following formula (hereinafter, referred to as The Present Compound (36) ) was obtained in the similar way as Production Example 5.
The Present Compound (36) X H NMR (CDCI3) : δ ppm: 0.91 (3H, t) , 1.36 .(4H, dq) ,
2.12-2.18 (2H, m) , 2.26 (3H, s), 3.14-3.20 (1H, m) , 3.34
(1H, dd) , 3.49-3.56 (1H, m) , 3.60 (1H, dd) , 3.66-3.79 (5H, m) , 5.59 (1H, s), 5.78 (1H-, s), 6.03-6.06 (2H, m)
Production Example 37
Using 0.20 g of (2E, 4E) -3-methylnona-2 , 4-dienoic acid
(Reference Production Example 11) instead of 0.63 g of (2E, 4E) -hepta-2 , -dienoic acid, and 0.12 g of (tetrahydropyran- 3-yl) methylamine instead of 0.54 g of (tetrahydrofuran-3- yl) methylamine hydrochloride, 0.19 g of (2E, 4E)-N-
(tetrahydropyran-3-ylmethyl) -3-methylnona-2 , 4-dienamide of the following formula (hereinafter, referred to as The Present Compound (37)) was obtained in the similar way as Production Example 5.
The Present Compound (37)
X H NMR (CDCI3) : δ ppm: 0.91 (3H, t) , 1.25-1.45 (4H, m) , 1.53-1.68 (3H, m) , 1.77-1.8.9 (2H, m) , 2.11-2.19 (2H, m) , 2.26 (3H, d) , 3.18-3.23 (3H, m) , 3.38-3.44 (1H, m) , 3.80- 3.89 (2H, m) , 5.49 (1H, br s) , 5.57 (1H, d) , 6.02-6.05 (2H, m) Production Example 38
Using 0.21 g of (2E, 4E) -nona-2 , 4-dienoic acid instead of 0.63 g of (2E, 4E) -hepta-2 , 4-dienoic acid, and 0.11 g of (tetrahydropyran-3-yl) methylamine instead of 0.54 g of (tetrahydrofuran-3-yl) methylamine hydrochloride, 0.15 g of (2E, 4E) -N- (tetrahydropyran-3-ylmethyl ) nona-2 , 4-dienamide of the following formula (hereinafter, referred to as The Present Compound (38)) was obtained in the similar way as Production Example 5.
The Present Compound (38)
X H NMR (CDC1 3 ) : δ ppm: 0.90 (3H, t), 1.23-1.44 (4H, m) , 1.54-1.67 (3H, m) , 1.78-1.88 (2H, m) , 2.15 (2H, q) , 3.18-3.26 (3H, m) , 3.37-3.45 (lH, m) , 3.79-3.89 (2H, m) , 5.50 (1H, s), 5.73 (1H, d) , 6.04-6.17 (2H, m) , 7.19 (1H, dd)
Production Example 39
Using 0.15 g of (2E, 4E) -nona-2 , 4-dienoic acid instead of 0.63 g of (2E, 4E) -hepta-2 , 4-dienoic acid, and 0.17 g of ( 5-ethyl-l , 3-dioxan-5-yl ) methylamine instead of 0.54 g of (tetrahydrofuran-3-yl) methylamine hydrochloride, 0.11 g of (2E, 4E) -N- (5-ethyl-l, 3-dioxan-5-ylmethyl ) nona dienamide of the following formula (hereinafter, referred to as The Present Compound (39)) was obtained in the similar way as Production Example 5.
The Present Compound (39)
X H N R (CDC1 3 ) : δ ppm: 0.87-0.92 (6H, m) , 1.23-1.44
(6H, m) , 2.15 (2H, q) , 3.53 (2H, d) , 3.57 (2H, d) , 3.79 (2H, d) , 4.67 (lH, d) , 4.97 (1H, d) , 5.76 (1H, d) , 5.81 (1H, br s), 6.03-6.18 (2H, m) , 7.20 (1H, dd)
Production Example 40
Using 0.15 g of (2E, 4E) -nona-2 , 4-dienoic acid instead of 0.63 g of (2E, 4E) -hepta-2 , -dienoic acid, and 0.14 g of (1, 4-dioxan-2-yl ) methylamine instead of 0.54 g of (tetrahydrofuran-3-yl)methylamine hydrochloride, 0.12 g of (2E, 4E) -N- ( 1 , 4-dioxan-2-ylmethyl ) nona-2 , 4-dienamide of the following formula (hereinafter, referred to as The Present ^ Compound (40)) was obtained in the similar way as Production Example 5. The Present Compound (40)
1 ti NMR (CDC1 3 ) : δ ppm:0.90 (3H, t) , 1.28-1.44 (4H, m) , 2.16 (2H, q) , 3.20 ( 1H, ddd) , 3.33 (1H, dd) , 3.54-3.62 (2H, m) , 3.67-3.80 (5H, m) , 5.76 (1H, d) , 5.81 (1H, br s) , 6.04- 6.18 (2H, m) , 7.20 (1H, dd)
Production Example 41
Using 0.20 g of (2E, 4E) -nona-2 , 4-dienoic acid instead of 0.63 g of (2E, 4E) -hepta-2, 4-dienoic acid, and 0.30 g of ( 3-methyltetrahydrofuran-3-yl) methylamine instead of 0.54 g of (tetrahydrofuran-3-yl ) methylamine hydrochloride, 0.29 g of (2E, 4E) -N- ( 3-methyltetrahydrofuran-3-ylmethyl ) nona-2, 4- dienamide of the following formula (hereinafter, referred to as The Present Compound (41) ) was obtained in the similar way as Production Example 5.
The Present Compound (41)
X H NMR (CDCI3) : δ ppm: 0.90 (3H, t) , 1.12 (3H, s), 1.28-1.45 (4H, m) , 1.65-1.70. ( 1H, m) , 1.82-1.90 (1H, m) , 2.16 (2H, q) , 3.31-3.43 (3H, m) , 3.66 (1H, d) , 3.81-3.88 (1H, m) , 3.90-3.97 (1H, m) , 5.74 (1H, br s), 5.76 (1H, d) , 6.04-6.17 (2H, m) , 7. ' 20 (1H, dd) Production Example 42
Using 0.20 g of (2E, 4E) -nona-2 , 4-dienoic acid instead of 0.63 g of (2E, 4E) -hepta-2 , 4-dienoic acid, and 0.29 g of 2- (tetrahydrofuran-2-yl ) ethylamine instead of 0.54 g of (tetrahydrofuran-3-yl ) methylamine hydrochloride, 0.13 g of (2E, 4E) -N- [2- (tetrahydrofuran-2-yl) ethyl] nona-2, 4- dienamide of the following formula (hereinafter, referred to as The Present Compound (42)) was obtained in the similar wa as Production Example 5.
The Present Compound (42)
X H NMR (CDC1 3 ) : δ ppm: 0.90 (3H, t) , 1.27-1.43 (4H, m) , 1.46-1.55 (1H, m) , 1.59-1.72 (1H, m) , 1.80-1.93 (3H, m) , 1.98-2.06 (1H, m) , 2.14 (2H, q) , 3.32 (1H, dq) , 3.61 (1H, dt), 3.74 (lH, td) , ■ 3.85-3.94 (2H, m) , 5.74 (1H, d) , 6.01- 6.16 (2H, m) , 6.30 (1H, s), 7.16 (1H, dd)
Production Example 43
Using 0.20 g of (2E, 4E) -nona-2 , 4-dienoic acid instead of .0.63 g of (2E, 4E) -hepta-2 , 4-dienoic acid, and 0.39 g of 2- (tetrahydrofuran-3-yl) ethylamine hydrochloride instead of 0.54 g of (tetrahydrofuran-3-yl ) methylamine hydrochloride, 0.13 g of (2E, 4E) -N- [2- (tetrahydrofuran-3-yl ) ethyl] nona- 2, 4-dienamide of the, following formula (hereinafter, referred to as The Present Compound (43) ) was obtained in the similar wa as Production Example 5.
The Present Compound (43)
¾ NMR (CDC1 3 ) : δ ppm:0.90 (3H, t), 1.27-1.44 (4H, m) , 1.50-1.68 (3H, m) , 2.04-2.26 (4H, m) , 3.32-3.40 (3H, m) , 3.75 (1H, q) , 3.83-3.94 (2H, m) , 5.51 (1H, s) , 5.72 (1H, d) , 6.03-6.16 (2H, m) , 7.19 (1H, dd)
Production Example 44
Using 0.20 g of (2E, 4E) -nona-2 , 4-dienoic acid instead of 0.63 g of (2E, 4E) -hepta-2, 4-dienoic acid, and 0.34 g of 2- (tetrahydropyran-4-yl) ethylamine instead of 0.54 g of (tetrahydrofuran-3-yl ) methylamine hydrochloride, 0.11 g of (2E, 4E) -N- [2- (tetrahydropyran-4-yl) ethyl] nona-2, 4- dienamide of the following formula (hereinafter, referred to as The Present Compound (44)) was obtained in the similar wa as Production Example 5.
The Present Compound (44)
1 R NMR (CDCI3) : δ ppm: 0.90 (3H, t) , 1.25-1.66 (11H, m) , 2.15 (2H, q) , 3.33-3.41 (4H, m) , 3.95 (2H, dd) , 5.40 (1H, s), 5.72 (1H, d) , 6.03-6.17 (2H, m) , 7.19 (1H, dd) Production Example 45
Using 0.50 g of (2E, 4E) -deca-2 , 4-dien-9-ynoic acid (Reference Production Example 8) instead of 0.63 g of (2E, 4E) -hepta-2, 4-dienoic acid, 0.11 g of (2E, 4E) -N- (tetrahydrofuran-3-ylmethyl) deca-2, 4-dien-9-ynamide of the following formula (hereinafter, referred to as The Present Compound (45) ) was obtained in the similar way as Production Example 5.
The Present Compound (45)
X H NMR (CDC1 3 ) : δ ppm: 1.57-
1.69 (3H,m) , 1.96 (1H, t) ,2.01-2.12 (lH,m) , 2.15-2.31 ( 4H, m) ,2.42- 2.56(lH,m) , 3.29-3.40 (2H,m) , 3.50-3.59 ( 1H, m) ,3.69- 3.91(3H,m) ,5.70 (lH,s) ,5.76 (lH,d) ,6.01-6.09 (lH,m) , 6.14- 6.21(lH,m) ,7.19(lH,dd)
Production Example 46
Using 0.50 g of (2E, 4E) -deca-2, 4-dien-9-ynoic acid (Reference Production Example 8) instead of 0.63 g of (2E, 4E) -hepta-2 , 4-dienoic acid, and 0.52 g of (tetrahydropyran- 4-yl) methylamine instead of 0.54 g of (tetrahydrofuran-3- yl) methylamine hydrochloride, 0.26 g of (2E, 4E)-N- (tetrahydropyran-4-ylmethyl) deca-2, 4-dien-9-ynamide of the following formula (hereinafter, referred to as The Present Compound (46)) was obtained in the similar way as Production Example 5.
The Present Compound (46)
1 R NMR (CDCI 3 ) : δ ppm: 1.31 ( 2H, dq) , 1.52- 1.66 (4H,m) , 1.72-
1.85 (lH,m) ,1.97 (lH,t) ,2.19 (2H,dt) ,2.28 (2H,dt) ,3.24 (2H,t) ,3. 36 C2H, t) , 3.92-3.99 (2H,m) , 5.51 (1H, s) , 5.75 (lH,d) , 5.97- 6.07 (lH,m) , 6.12-6.20 (lH,m) , 7.19 (lH,dd)
Production Example 47
Using 0.45 g of (2E, 4E) -undeca-2 , 4-dien-lO-ynoic acid instead of 0.63 g of (2E, 4E) -hepta-2 , 4-dienoic acid, and 0.38 g of ( tetrahydropyran-2-yl ) methylamine instead of 0.54 g of (tetrahydrofuran-3-yl) methylamine hydrochloride, 0.29 g of (2E, 4E) -N- ( tetrahydrofuran-2-ylmethyl ) undeca-2, 4- dien-10-ynamide of the following formula (hereinafter, referred to as The Present Compound (47)) was obtained in the similar way as Production Example 5.
The Present Compound (47)
1 H NMR (CDCI3) : δ ppm: 1. 6-1.59 ( 5H, m) , 1.81- 2.02 (4H,m) ,2.12-2.24 (4H,m) ,3.17-3.26 (lH,m) ,3.57- 3.67 (lH,m) ,3.70-3.77 (lH,m) , 3.81-3.89 ( 1H, m) ,3.91- 3.99(lH,m) ,5.78 (lH,d) ,5.97 (lH,s) , 5.99- 6.18 (2H,m) ,7.20 (lH,dd)
Production Example 48
Using 0.45 g of (2E, 4E) -undeca-2 , 4-dien-lO-ynoic acid instead of 0.63 g of (2E, 4E) -hepta-2 , 4-dienoic acid, 0.24 g of (2E, 4E) -N- ( tetrahydrofuran-3-ylmethyl ) undeca-2, 4- dien-10-ynamide of the following formula (hereinafter, referred to as The Present Compound (48)) was obtained in the similar way as Production Example 5.
The Present Compound (48)
X H NMR (CDCI 3 ) : δ ppm: 1.48-
1.67 (5H,m) , 1.96 (1H, t) , 1.98-2.08 (lH,m) , 2.11-2.22 (4H,m) , 2.42- 2.54 (lH,m) ,3.25-3.41(2H,m) ,3.50-3.56(lH,m) ,3.68- 3.96 (3H,m) , 5.78 (1H, d) , 5.97 (1H, s) , 6.01- 6.19(2H,m) ,7.20(lH,dd)
Production Example 49
Using 0.45 g of (2E, 4E) -undeca-2 , 4-dien-lO-ynoic acid instead of 0.63 g of (2E, 4E) -hepta-2 , 4-dienoic acid, and 0.44 g of ( tetrahydropyran-4-yl ) methylamine instead of 0.54 g of (tetrahydrofuran-3-yl) methylamine hydrochloride, 0.44 g of (2E, 4E) -N- (tetrahydropyran-4-ylmethyl) undeca-2, 4- dien-10-ynamide of the following formula (hereinafter, referred to as The Present Compound (49) ) was obtained in the similar way as Production Example 5.
The Present Compound (49)
X H NMR (CDC1 3 ) : δ ppm: 1.24-1.36 (2H,m) , 1.47- 1.65(6H,m) ,1.72-1.86 (lH,m) ,1.95 (lH,t) , 2.09-2.26 (4H,m) ,3.17- 3.27 (2H,m) , 3.32-3.41 (2H,m) , 3.90- 4.00 (2H,m) , 5.77 (lH,d) , 5.79 (1H, s) , 6.01- 6.18(2H,m) ,7.20(lH,dd) Production Example 50
Using 0.31 g of (2E, 4E) -nona-2 , 4 , 8-trienoic acid (Reference Production Example 7) instead of 0.63 g of (2E, 4E) -hepta-2 , 4-dienoic acid, and 0.35 g of ( tetrahydropyran- 4-yl ) methylamine instead of 0.54 g of (tetrahydrofuran-3"- yl ) methylamine hydrochloride, 0.41 g of (2E, 4E)-N- (tetrahydropyran-4-ylmethyl) nona-2, 4, 8-trienamide of the following formula (hereinafter, referred to as The Present Compound (50) ) was obtained in the similar way as Production Example 5.
The Present Compound (50)
X H NMR (CDC1 3 ) : δ ppm: 1.24-1.37 (2H,m) , 1.57- 1.68 (2H,m) , 1.74-1.86 (lH,m) ,2.14-2.20 (4H,m) , 3.20- 3.28 (2H,m) , 3.31-3.40 (2H,m) , 3.91-3.99 (2H,m) , 4.95- 5.06 (2H,m) , 5.58 (1H, s) , 5.70-5.85 (2H,m) , 6.04- 6.18 (2H,m) ,7.20 (lH,dd) Production Example 51
Using 0.81 g of (2E, 4E) -3-methylnona-2, -dienoic acid (Reference Production Example 11) instead of 0.63 g of (2E, 4E)-hepta-2, 4-dienoic acid, and 0.32 g of ( 5-methyl-l , 3- dioxan-5-yl) methylamine instead of 0.54 g of (tetrahydrofuran-3-yl ) methylamine hydrochloride, 0.40 g of (2E, 4E) -N- (5-methyl-l, 3-dioxan-5-yl) -3-methylnona-2, 4- dienamide of the following formula (hereinafter, referred to as The Present Compound (51) ) was obtained in the similar way as Production Example
The Present Compound (51)
X H NMR (CDC1 3 ) : δ ppm:0.83 (3H, s), 0.91 (3H, t) , 1.29-1.45 (4H, m) , 2.12-2.19 (2H, m) , 2.26 (3H, d) , 3.46 (2H, d) , 3.49 (2H, d) , 3.77 (2H, d) , 4.68 (1H, d) , 4.96 (1H, d) , 5.60 (1H, s), 5.73 (1H, b r s), 6.03-6.05 (2H, m)
Production Example 52
Using 0.74 g of (2E, 4E) -nona-2 , 4-dienoic acid instead of 0.63 g of (2E, 4E)-hepta-2, 4-dienoic acid, and 0.32 g of (5-methyl-l, 3-dioxan-5-yl ) methylamine instead of 0.54 g of (tetrahydrofuran-3-yl) methylamine hydrochloride, 0.23 g of (2E, 4E) -N- ( 5-methyl-l , 3-dioxan-5-yl ) nona-2 , 4-dienamide of the following formula (hereinafter, referred to as The Present Compound (52)) was obtained in the similar way as Production Example 5.
The Present Compound (52)
X H NMR (CDCI 3 ) : δ ppm: 0.82 (3H, s) , 0.90 (3H, t) , 1.24-1.44 (4H, m) , 2.15 (2H, q) , 3.46 (2H, d) , 3.53 (2H, d) , 3.78 (2H, d) , 4.68 (1H, d) , 4.96 (1H, d) , 5.76 (1H, d) , 5.79 (1H, br s), 6.03-6.18 (2H, m) , 7.20 (1H, dd)
Production Example 53
Using 0.83 g of (tetrahydrofuran-3-yl) methylamine hydrochloride instead of 0.69 g of (tetrahydrofuran-2- yl) methylamine, 0.10 g of (2EZ, 4E) -N- (tetrahydrofuran-3- ylmethyl) -3-methylnona-2, 4-dienamide of the following fomula (hereinafter, referred to as The Present Compound (53)) was obtained as a mixture of higher polarly fraction and lower polarly fraction in the similar way as Production Ex mple 20,
The Present Compound (53)
XH NMR (CDC1 3 ) : δ ppm: 0.88-0.93 (3. OH, m) , 1.28-1.45
(4. OH, m) , 1.59-1.67 (1. OH, m) , 1.94 (0.6H, d) , 2.00-2.09 (1.0H, m) , 2.10-2.23 (2. OH, m) , 2.26 (2.4H, d) , 2.46-2.56 (1.0H, m) , 3.18-3.38 (2. OH, m) , 3.51-3.56 (1.0H, m) , 3.69- 3.91 (3. OH, m) , 5.48 (0.2H, s), 5.57 (0.8H, s), 5.61 (1.0H, br s), 5.99-6.11 (1.8H, m) , 7.54 (0.2H, d)
[0148]
Next, Reference Production Examples of the intermediate using for producing the present compound are shown below.
[0149]
Reference Production Example 1
To a mixture of 25 g of ( tetrahydrofuran-3-yl ) methanol of the following formula:
and 125 ml of pyridine, 56 g of p-toluenesulfonyl chloride was added under nitrogen atmosphere and under ice-cooling, and stirred for 4 hours under ice-cooling. To the reaction mixture, water was added and extracted with tert-butyl methyl ether 2 times. The organic layer was washed with 1 mol/1 of hydrochloric acid and brine successively. The organic layer was dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure to obtain 58 g of a crude product of p- toluenesulfonic acid tetrahydrofuran-3-ylmethyl ester of the following formula.
The crude product was used for Reference Production Example 2 without further purification.
[0150] Reference Production Example 2
Under nitrogen atmosphere, to a mixture of 29 g of p- toluenesulfonic acid tetrahydrofuran-3-ylmethyl ester, 23 g of potassium iodide and 300 ml of N, N-dimethylformamide, 22 g of phthalimide potassium salt was added, . and stirred for 3 hours at 80 °C. After ice-cooling, to the reaction mixture, water was added and stirred for 30 minutes, then filtered. The resulting solid was collected and dried under reduced pressure to obtain 14 g of 2- (tetrahydrofuran-3-ylmethyl) isoindol-1, 3-dione of the following formula.
1 H NMR (CDC1 3 ) : δ ppm: 7.86 (2H, dd) , 7.73 (2H, dd) , 3.94 (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)
[0151]
Reference Production Example 3
Under nitrogen atmosphere, to a mixture of 14 g of 2- (tetrahydrofuran-3-ylmethyl ) isoindol-1 , 3-dione and 150 ml of ethanol, 4.6 g of hydrazine monohydrate was added, and stirred for 6 hours at 70 °C. The reaction mixture was filtered, then obtained residue was washed with ethanol. To the ethanol solution, 1 ml of a suspension of Raney nickel (trademark) was added, and stirred for 4 hours at 60 °C. The reaction liquid was allowed to cool to room temperature, and filtered. To the filtrate, 90 ml of 1 mol/1 hydrogen chloride in diethyl ether was added, and concentrated under reduced pressure to obtain 10 g of crude preduct of (tetrahydrofuran-3-yl) methylamine hydrochloride of the following formula.
The crude product was used for next process of production without further purification.
[0152]
Reference Production Example 4
Under nitrogen atmosphere, a mixture of 1.5 g of (3- methyloxetan-3-yl ) methanol of the following formula
and 150 ml of pyridine, 33 g of p-toluenesulfonyl chloride was added, and stirred for 4.5 hours under ice-cooling. To the reaction mixture, water was added and extracted with ethyl acetate 2 times. The organic layer was washed with 1 mol/1 of hydrochloric acid and brine successively. The organic layer was dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give 28 g of p-toluenesulfonic acid 3- methyloxetan-3-ylmethyl ester of the following formula.
X H NMR (CDC1 3 ) : δ ppm: 7.81 (2H, d) , 7.37 (2H, d) , 4.36 (4H, dd) , 4.11 (2H, s) , 2.47 (3H, s), 1.31 (3H, s)
[0153]
Reference Production Example 5
Under nitrogen atmosphere, a mixture of 13 g of p- toluenesulfonic acid 3-methyloxetan-3-ylmethyl ester, 13 g of potassium iodide and 150 ml of N, N-dimethylformamide, 8.3 g of phthalimide potassium salt was added, and stirred for 7 hours at 60 °C. After ice-cooling, to the reaction mixture, water was added and stirred for 30 minutes, then filtered. The resulting solid was collected and dried under reduced pressure to obtain 5.1 g of 2- (3- methyloxetan-3-ylmethyl) isoindol-1, 3-dione of the following formula.
X H NMR (CDCI3) : δ ppm: 7.87 (2H, dd) , 7.75 (2H, dd) , (2H, d) , 4.36 (2H, d) , 3.87 (2H, s), 1.36 (3H, s)
[0154] Reference Production Example 6
Undere nitrogen atmosphere, a mixture of 5.0 g of 2- ( 3-methyloxetan-3-ylmethyl ) isoindol-1 , 3-dione and 40 ml of methanol, 1.1 g of hydrazine monohydrate was added, and stirred for 8 hours under reflux. To the reaction liquid allowed to cool to room temperature, 90 ml of 1 mol/1 of hydrogen chloride in diethyl ether was added, and concentrated under reduced pressure to obtain 7.1 g of crude . product of ( 3-methyloxetan-3-yl ) methylamine hydrochloride of the following formula.
The crude product was . used for next process of production without further purification.
[0155]
Reference Production Example 7
By hydrolyzing an ethyl ester compound represented by the following formula A in the presense of potassium hydroxide in the similar way as the method described in Tetrahedron Letters, Vol. 26, No.21, pp 2317 - 2520 (1985), (2E, 4E) -nona-2 , 4 , 8-trienoic acid was obtained.
(2E, 4E) -nona-2 , , 8-trienoic acid X H NMR (CDCI3) : δ ppm: 2.22 (m, 2H) , 2.28 (m, 2H) , 5.00-5.07 (m, 2H) , 5.75-5.85 (m, 2H) , 6.14-6.26 (m, 2H) , 7.34 (dd, 1H)
[0156]
Reference Production Example 8
By hydrolyzing an ethyl ester compound represented by the following formula B in the presense of potassium hydroxide in the similar way as the method described in Journal of the American Chemical Society, Vol. 113, pp 5066 - 5068 (1991), (2E, 4E) -deca-2 , 4-dien-9-ynoic acid was obtained.
(2E, 4E) -deca-2, 4-dien-9-ynoic acid
1 H NMR (CDCI3) : δ ppm: 1.68 (m, 2H) , 2.20-2.33 (m, 5H) , 5.80 (d, 1H), 6.12-6.28 (m, 2H) , 7.34 (dd, 1H)
[0157]
Reference Production Example 9
By hydrolyzing an ethyl ester compound represented by the following formula C in the presense of potassium hydroxide in the similar . way as the method described in Tetrahedron Letters, Vol. 26, No.21, pp 2317 - 2520 (1985), (2E, 4E) -deca-2 , 4 , 9-trienoic acid was obtained.
(2E, 4E) -deca-2, 4, 9-trienoic acid
X H NMR (CDC1 3 ) : δ ppm: 1.55 (m, 2H) , 2.07 (m, 2H) , 2.21 (m, 2H) , 4.96-5.05 (m, 2H) , 5.74-5.85 (m, 2H) , 6.14- 6.21 (m, 2H) , 7.36 (dd, 1H)
[0158]
Reference Production Example 10
By hydrolyzing an ethyl ester compound represented by the following formula D synthesized as following scheme in the presense of potassium hydroxide, (2E, 4E)-6- butyloxyhexa-2 , 4-dienoic acid was obtained.
Synthesis of the ethyl ester compound of formula D described above:
To 20 ml of tetrahydrofuran anhydrous, sodium hydride
(purity; 55 %, 0.54 g, 12.4 mmol) was added. To the mixture, a solution of triethyl 4-phosphonocrotonate (3.10 g, 12.4 mmol) in tetrahydrofuran anhydrous (7 ml) was dropwised under ice-cooling, and stirred for 30 minutes under ice-cooling and for 1 hour at room temperature. To the mixture, a solution of butoxyacetaldehyde (1.20 g, 10.3 mmol) in tetrahydrofuran anhydrous (5 ml) was dropwised under ice-cooling and stirred for 2 hours under ice-cooling. To the reaction liquid, a mixture of 20 ml of 5 % of hydrochloric acid and 30 ml of. ice-water was added, and extracted with 100ml of ethyl acetate 2 times. The ethyl acetate layers were collectively washed with 20 ml of aqueous saturated sodium hydrogen carbonate solution and 30 mi of brine successively, and dried over magnesium sulfate, then concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give 0.58 g of the ethyl ester compound of formula D described above.
1 H NMR (CDC1 3 ) : δ ppm: 0.93 (t, 3H) , 1.29 (t, 3H) , 1.40 (m, 2H), 1.57 (m, 2H) , 3.45 (m, 2H) , 4.08 (d, 2H) , 4.22 (q, 2H) , 5.88 (d, 1H) , 6.17 (dt, 1H) , 6.36 (m, 1H) , 7.27 (m, 1H).
Reference Production Example 11
Under nitrogen atmosphere, 10.4 g of (2EZ, 4E)-3- methylnona-2, 4-dienoic acid ( (2E, 4E) -Form : (2Z, 4E)-Form = 2 : 1) and dissolved with 20 ml of hexane. The obtained solution was placed in cold strage and crystallized, then filtered to obtain 2.4 g of (2E, 4E) -3-methylnona-2 , 4- dienoic acid as the resulting crystals.
(2E, 4E) -3-methylnona-2 , -dienoic acid
X H NMR (CDC1 3 ) : δ ppm: 0.91 (3H, t), 1.28-1.46 (4H, m) , 2.19 (2H, q) , 2.28 (3H, d) , 5.72 (1H, s), 6.10-6.23 (2H, m) [0159]
Concrete examples of the present compound are as follows. In the following examples, marks described as XI to X20 and Yl to YIO are represented as follows respectively .
X1 X2 X3 X4 X5 X6
X16
X17 X18
[0160]
Y1 Y2 Y3 Y4 Y5
Y6 Y7 Y8 Y9 Y10
[0161]
A compound represented by formula
wherein, a combination of X and Y is any one of the combinations indicated in [Table 1] to [Table 5].
[0162]
A compound represented by formula (1-20);
wherein, a combination of X and Y is any one of the combinations indicated in [Table 1] to [Table 5] .
[0163]
A compound represented by formula (1-21) ; wherein, a combination of X and Y is any one of the combinations indicated in [Table 1] to [Table 5] .
[0164]
A compound represented by formula (1-22);
wherein, a combination of X- and Y is any one of the combinations indicated in [Table 1] to [Table 5] .
[0165]
A compound represented by formula (1-23);
wherein, a combination of X and Y is any one of the combinations indicated in [Table 1] to [Table 5] .
[0166]
A compound represented by formula (1-24); wherein, a combination of X and Y is any one of the combinations indicated in [Table 1] to [Table 5] .
[0167]
A compound represented by formula (1-25) ;
wherein, a combination of X and Y is any one of the combinations indicated in [Table 1] to [Table 5] .
[0168]
A compound represented by formula (1-26);
wherein, a combination of X and Y is any one of the combinations indicated in [Table 1] to [Table 5] .
[0169]
A compound represented by formula (1-27); wherein, a combination of X and Y is any one of the combinations indicated in [Table 1] to [Table 5] .
[0170]
A compound represented by formula (1-28);
wherein, a combination of X and Y is any one of the combinations indicated in [Table 1] to [Table 5] .
[0171]
A compound represented by formula (1-29) ;
wherein, a combination of X and Y is any one of the combinations indicated in [Table 1] to [Table 5] .
[0172]
A compound represented by formula (1-30) ; wherein, a combination of X and Y is any one of the combinations indicated in [Table 1] to [Table 5] .
[0173]
A compound represented by formula (1-31);
wherein, a combination of X and Y is any one of the combinations indicated in [Table 1] to [Table 5] .
[0174]
A compound represented by formula (1-32) ;
wherein, a combination of X and Y is any one of the combinations indicated in [Table 1] to [Table 5] .
[0175]
A compound represented by formula (1-33) ; wherein, a combination of X and Y is any one of the combinations indicated . in [Table 1] to [Table 5].
[0176]
Regarding to compounds represented by formula (1-19) to (1-33), combinations of X and Y are as follows. In the following Tables, a number of the combinations, a group represented by X, and a group represented by Y are indicated in turn.
[0177]
[Table 1]
No. X Y
1 XI Yl
2 XI Y2
3 XI Y3
4 XI Y4
5 XI Y5
6 XI Y6
7 XI Y7
8 XI Y8
9 XI Y9
10 XI Y10
11 X2 Yl
12 X2 Y2
13 X2 Y3
14 X2 Y4
15 X2 Y5
16 X2 Y6
17 X2 Y7
18 X2 Y8
19 X2 Y9
20 X2 Y10
[Table 1 (continued) ]
No. X Y
21 X3 Yl
22 X3 Y2
23 X3 Y3
24 X3 Y4
25 X3 Y5
26 X3 Y6
27 X3 Y7
28 X3 Y8
29 X3 Y9
30 X3 Y10
31 X4 Yl
32 X4 Y2
33 X4 Y3
34 X4 Y4
35 X4 Y5
36 X4 Y6
37 X4 Y7
38 X4 Y8
39 X4 Y9
40 X4 Y10
[0178]
[Table 2]
No. X Y
41 X5 Yl
42 X5 Y2
43 X5 Y3
44 X5 Y4
45 X5 Y5
46 X5 Y6
47 X5 Y7
48 X5 Y8
49 X5 Y9
50 X5 YIO
51 X6 Yl
52 X6 Y2
53 X6 Y3
54 X6 Y4
55 X6 Y5
56 X6 Y6
57 X6 Y7
58 X6 Y8
59 X6 Y9
60 X6 YIO
[Table 2 (continued) ]
No. X Y
61 X7 Yl
62 X7 Y2
63 X7 Y3
64 X7 Y4
65 X7 Y5
66 X7 Y6
67 X7 Y7
68 X7 . Y8
69 X7 Y9
70 X7 Y10
71 X8 Yl
72 X8 Y2
73 X8 Y3
74 X8 Y4
75 X8 Y5
76 X8 Y6
77 X8 Y7
78 X8 Y8
79 X8 Y9
80 X8 Y10
[0179]
[Table 3]
No. X Y
81 X9 Yl
82 X9 Y2
83 X9 Y3
84 X9 Y4
85 X9 Y5
86 X9 Y6
87 X9 Y7
88 X9 Y8
89 X9 Y9
90 X9 YIO
91 XIO Yl
92 XIO Y2
93 XIO Y3
94 XIO Y4
95 XIO Y5
96 XIO Y6
97 XIO Y7
98 XIO Y8
99 .XIO Y9
100 XIO YIO
[Table 3 (continued) ]
No. X Y
101 Xll Yl
102 Xll Y2
103 Xll Y3
104 Xll Y4
105 Xll Y5
106 Xll Y6
107 Xll Y7
108 Xll Y8
109 Xll Y9
110 Xll Y10
111 X12 Yl
112 X12 Y2
113 X12 Y3
114 X12 Y4
115 X12 Y5
116 X12 Y6
117 X12 Y7
118 X12 Y8
119 X12 Y9
120 X12 Y10
[0180]
[Table 4]
No. X Y
121 X13 Yl
122 X13 Y2
123 X13 Y3
124 X13 Y4
125 X13 Y5
126 X13 Y6
127 X13 Y7
128 X13 Y8
129 X13 Y9
130 X13 YIO
131 X14 Yl
132 X14 Y2
133 X14 Y3
134 X14 Y4
135 X14 Y5
136 X14 Y6
137 X14 Y7
138 X14 Y8
139 X14 Y9
140 X14 YIO
[Table 4 (continued)]
No. X Y
141 X15 Yl
142 X15 Y2
143 X15 Y3
144 X15 Y4
145 X15 Y5
146 X15 Y6
147 X15 Y7
148 X15 Y8
149 X15 Y9
150 X15. Y10
151 X16 Yl
152 X16 Y2
153 X16 Y3
154 X16 Y4
155 X16 Y5
156 X16 Y6
157 X16 Y7
158 X16 Y8
159 X16 Y9
160 X16 Y10
[0181]
[Table 5]
[0182]
Formulation Examples are shown below. Parts are by weight.
Formulation Example 1
Twenty (20) parts of each of the Present Compounds (1) to (53) is dissolved in 65 parts of xylene and 15 parts of SOLPOL 3005X (a registered trademark of TOHO Chemical
Industry Co., Ltd.) is added thereto and thoroughly mixed with stirring to obtain emulsifiable concentrates.
[0183] Formulation Example 2
Five (5) parts of SORPOL 3005X is added to 40 parts of each of the Present Compounds (1) to (53) and the mixture is thoroughly mixed, and 32 parts of CARPLEX #80 (synthetic hydrated silicon oxide, a registered trademark of SHIONOGI & CO., LTD.) and 23 parts of 300-mesh. diatomaceous earth are added thereto, followed by mixing with stirring by a mixer to obtain wettable powders.
[0184]
Formulation Example 3
A mixture of 1.5 parts of each of the . Present
Compounds (1) to (53), 1 part of TOKUSIL GUN (synthetic hydrated silicon oxide, manufactured by Tokuyama
Corporation), 2 parts of REAX 85A (sodium lignin sulfonate, manufactured by West Vaco Chemicals), 30 parts of BENTONITE FUJI (bentonite, manufactured by Houjun) and 65.5 parts of SHOUKOUZAN A clay (kaoline clay, manufactured by Shoukouzan Kougyousho) is thoroughly pulverized and mixed, and water is added thereto. The mixture is thoroughly kneaded, granulated by an extruding granulator,. and then dried to obtain 1.5% granules.
[0185]
Formulation Example 4
To a mixture of 10 parts of each of the Present
Compounds (1) to (53), 10 parts of phenylxylylethane and 0.5 part of SUMIDUR L-75 (tolylene diisocyanate,
manufactured by Sumitomo Bayer. Urethane Co., Ltd.) is added 20 parts of 10% aqueous solution of gum arabic, and the mixture is stirred with a homomixer to obtain an emulsion having an average particle diameter of 20 μτ . To the emulsion, 2 parts of ethylene glycol is added and the mixture is further stirred in a warm bath at a temperature of 60°C for 24 hours to obtain microcapsule slurry. On the other hand, 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 thickener solution. Then, 42.5 parts of the above-mentioned microcapsule slurry and 57.5 parts of the above-mentioned thickener solution are mixed to obtain microcapsules.
[0186]
Formulation Example 5
A mixture of 10 parts of each of the Present Compounds (1) to (53) and 10 parts of phenylxylylethane is added to 20 parts of a 10% aqueous solution of polyethylene glycol, and the mixture is stirred by a homomixer to obtain an emulsion having an average particle diameter of 3 μπι. On the other hand, 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 thickener solution. Then, 40 parts of the above-mentioned emulsion solution and 60 parts of the above-mentioned thickener solution are mixed to obtain flowable formulations.
[0187]
Formulation Example 6
To 5 parts of each of the Present Compounds (1) to (53), 3 parts of CARPLEX #80 (synthetic hydrated silicon oxide, a registered trademark of SHIONOGI & CO., LTD.), 0.3 part of PAP (a mixture of monoisopropyl phosphate and diisopropyl phosphate) and 91.7 parts of talc (300 mesh) are added and the mixture is stirred by a mixer to obtain dusts .
[0188]
Formulation Example 7
Zero point one (0.1) part of each of the Present
Compounds (1) to (53) is dissolved in 10 parts of
dichloromethane and the solution is mixed with 89.9 parts of deodorized kerosine to obtain oil solutions.
[0189]
Formulation Example 8
One (1) part of each of the Present Compounds. (1) to (53) 5 parts of dichloromethane and 34 parts of deodorized kerosine are mixed and dissolved, and the solution is filled into an aerosol container and a valve portion is installed. Then, 60 parts of power propellant (liquefied petroleum gas) is filled therein under pressure through the valve portion to obtain oil-based aerosol formulations.
[0190]
Formulation Example 9
Zero point six (0.6) part of each of the compounds (1) to (53)., 5 parts of xylene, 3.4 parts of deodorized
kerosine and 1 part of ATMOS 300 (emulsifier, a registered trademark of Atmos chemical) are mixed and dissolved, and the solution and 50 parts of water are filled into an aerosol container, and then 40 parts of power propellant (liquefied petroleum gas) is filled therein under pressure through a valve portion to obtain aqueous aerosol
formulations .
[0191]
Formulation Example 10
Zero point three (0.3) g of each of the Present
Compounds (1) to (53) is dissolved in 20 ml of acetone and the solution is uniformly mixed with stirring with 99.7 g of a base material for a coil (obtained by mixing Tabu powder, Pyrethrum marc and wooden powder at a ratio of 4:3:3). Then, 100 ml of, water is added thereto, and the mixture is thoroughly kneaded, dried and molded to obtain insecticidal coils.
[0192] Formulation Example 11
A mixture of 0.8 g of each of the Present Compounds (1) to (53) and 0.4 g of piperonyl butoxide is dissolved in acetone and the total volume is adjusted to 10 ml. Then, 0.5 ml of this solution is uniformly impregnated into a base material for an insecticidal mat for electric heating (a plate obtained by hardening fibrils of a mixture of cotton linters and pulp) having a size of 2.5 cm χ 1.5 cm and a thickness of 0.3 cm to obtain insecticidal mats for electric heating.
[0193]
Formulation Example 12
A solution obtained by dissolving 3 parts of each of the Present Compound (1) to (53) in 97 parts of deodorized kerosine is poured into a vessel made of vinyl chloride. A liquid absorptive core whose upper part can be heated by a heater (an inorganic pulverized powder is hardened with a binder and sintered) is inserted thereinto to obtain parts to be used for a liquid absorptive core type thermaltranspiring apparatus.
[0194]
Formulation Example 13
One hundred (100) mg of each of the Present Compound (1) to (53) is dissolved in an appropriate amount of acetone and the solution is impregnated into a porous ceramic plate having a size of 4.0 cm χ 4.0 cm and a thickness of 1.2 cm to obtain thermal fumigants.
[0195]
Formulation Example 14
One hundred (100) μg of each of the compound (1) to
(53) is dissolved in an appropriate amount of acetone and the solution is uniformly applied to filter paper having a size of 2 cm x 2 cm and a thickness of 0.3 mm, and air- dried to remove acetone, and thus volatile agents for using at room temperature are obtained.
Formulation Example 15
Ten parts of any one of the Present Compound (1) to (53) , 35 parts of white carbon containing 50 parts of a polyoxyethylene alkylether sulfate ammonium salt, and 55 parts of water are mixed and then finely-divided by a wet grinding method to obtain a formulation. [0196]
Next, it will be demonstrated by Test Examples that the Present Compound is effective as an active ingredient of a harmaful arthropod control agent.
[0197]
Test Example 1
The formulation of the Present Compound . obtained in the Formulation Example 7 was diluted with
isopropylaicohol/deodorized kerosene = 1/9 mixed solution so that the concentration of active ingredient was 0.5% (w/v) , to prepare a test solution.
Ten German cockroaches (5 of each male and female) were released in a test container (measuring 8.75 cm in diameter and 7.5 cm in height, bottom area covered with a 16 mesh wire netting) coated with butter at an inner wall, and the container was disposed on the bottom of a test chamber (bottom surface measuring 46 cm and 46 cm, 70 cm in height) .
From 60 cm in height above the container, each of 1.5 ml of the test solutions of the Present Compound (1) to (53) was sprayed using a spray gun (spray pressure: 0.42 kg/cm 2 ) . Thirty seconds after spraying, the container was removed from the test chamber and 5 minutes after, the number of knockdowned insects was counted and a knockdown rate was determined. The knockdown rate was calculated by - the following equation.
Knockdown rate (%) = (number of knockdowned
cockroaches/number of test cockroaches) x 100
As a result, in treatments with the Present Compound (1), (3), (4), (5), (6), (7), (8), (9), (10), (11), (12), . (13), (14), (15), (16), (17),. (18), (21), (22), (23), (24), (27), (28), (30), (31), (32), (33), (34), (35), (36), (37), (39), (41),. (47), (50), ' (51), (52) and (53), the knockdown rate was 90% or more.
[0198]
Test Example 2 , ■
- The formulation of the Present Compound obtained in the Formulation Example 7 was diluted with
isopropylaicohol/deodorized kerosene = 1/9 mixed solution so that the concentration of active ingredient was 0.1% (w/v) , to prepare a test solution.
Ten common house mosquitoes (Culex pipiens pallens) were left and bred in a polyethylene cup (bottom- diameter : 10.6 cm) which was then caped with 16-mesh nylon gauze. The polyethylene cup was placed on the bottom of a test chamber (46 cm x 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 using a spray gun at a spraying pressure of 0.4 kg/cm 2 . Immediately after
spraying, the cup was taken out from the test container, and ten minutes after, the number of knockdowned insects was counted and a knockdown rate was determined. The knockdown rate was calculated by the following equation.
Knockdown rate (%) = (number of knockdowned
insects/number of test insects) x 100
As a result, in treatments with the Present Compound (2), (3), (4), (6), (7), (8), (10), (11), (12), (13), (14), (15), (16), (18), (20), (22), (23), (24), (25), (26), (27), (28), (29), (31), (38), (39), (40), (41), (48), (51) and (53), the knockdown rate was 90% or more. Test Example 3
The formulation of any one of the Present Compound (22), (24), (27), (28), (29), (31), (38), (39), (40), (41), (48), (51) and (53) obtained in the Formulation Example 7 was diluted with isopropylaicohol/deodorized kerosene = 1/9 mixed solution so that the concentration of active ingredient was 0.02% (w/v) , to prepare a test solution.
Ten common house mosquitoes (Culex pipiens pallens) were left and bred in a polyethylene cup (bottom diameter : 10.6 cm) which was then caped with 16-mesh nylon gauze. The polyethylene cup was placed . on the bottom of a test chamber (46 cm x 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 using a spray gun at a spraying pressure of 0.4 kg/cm 2 . Immediately after spraying, the cup was taken out from the test container, and ten minutes after, the number of knockdowned insects was counted and a knockdown rate was determined. The knockdown rate was calculated by the following equation.
Knockdown rate (%) = (number of knockdowned insects/number of test insects) x 100 As a result, in treatments with the Present Compound (22), (24), (27), (28), (29), (31), (38), (39), (40), (41), (48), (51) and (53), the knockdown rate was 90% or more. Test Example 4
Formulation of any one of the Present Compound (6), (8), (13), (14), (20), (27), (29), (32), (41), (42), (43), (45), (46), (47), (50) and (51) was obtained according to Formulation Example 15. The formulation was diluted with water to prepare a test solution having 500 ppm of the active ingredient.
A filter paper having a diameter of 5.5 cm was spread on the bottom of a polyethylene cup having a diameter of 5.5 cm and 0.7 ml of the test solution was added dropwise onto the filter paper. As bait, 30 mg of sucrose was uniformly placed on the filter paper. Into the polyethylene cup, 10 female imagoes of housefly {Musca domestica) were released and the cup was sealed with a lid. After 2 hours, the number of knockdowned-housefly was counted and a knockdown rate was calculated according to the following equation.
Knockdown rate (%) = (number of knockdowned imagoes/number of tested imagoes) x 100
As a result,, the treatment with any one of the Present Compound (6), (8), (13), (14), (20), (27), (29), (32), (41), (42), (43), (45), (46), (47), (50) and (51) showed a knockdown rate of 100%.
Test Example 5
Formulation of any one of the Present Compound (37),
(38), (39), (44), (45), (46), (47), (49) and (51) was obtained according to Formulation Example 15. The formulation was diluted with water to prepare a test solution having 500 ppm of the active ingredient.
Into 100 ml of ion-exchanged water, 0.7 ml of the test, solution was added (the active ingredient concentration: 3.5 ppm). Into the solution; 20 last instar larvae of common house mosquitoes (Culex pipiens pallens) were released. After 8 days, ' the number of surviving or dead larve of common house mosquitoes was counted and a pest death rate was calculated according to the following equation. '
Pest death rate (%) = (Number of dead larvae/Number of tested larvae) x 100
As a result, the treatment with any one of the Present
Compound (37), (38), (39), (44), (45), (46), (47), (49) and (51) showed a pest death rate of 95% or more.
[0199]
Industrial Applicability The Present Compound has an excellent control effect on harmful arthropods. Thus, the Present Compound is effective as an active ingredient of a harmaful arthropod control agent.
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