JP2001026578A - N-substituted dihydropyrrole derivative - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a new N-substituted dihydropyrrole compound useful as an effective ingredient of agrochemicals capable of exhibiting excellent insecticidal activity against various noxious insects and also capable of exhibiting excellent herbicidal activity against various weeds. SOLUTION: This new N-substituted dihydropyrrole derivative is expressed by formula I [wherein R1 is H, a 1-6C alkyl, a 3-7C cycloalkyl, or the like; R2 and R3 are each H, a 1-6C alkyl or the like; R4 is H, a 2-10C alkylcarbonyl or the like; A is a 1-6C alkyl, a halogenlor the like; (n) is 1 to 5; and X is O, S, sulfinyl or sulfonyl], and is e.g. 5,5-dimethyl-4-hydroxy-1-methoxy-2- oxo-3-(2,4,6-trimethylphenyl)-2,5-dihydro-1H-pyrrole. The derivative of formula I is obtained e.g. by the acylation of an amino acid derivative of formula II (wherein R1a is the same as R1 except H; and R5 is H or a 1-6C alkyl), by cyclization and by introducing a substituent into the hydroxyl group.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

TECHNICAL FIELD The present invention relates to an N-substituted dihydropyrrole derivative, a salt thereof, an intermediate thereof, and an agricultural chemical containing the N-substituted dihydropyrrole derivative as an active ingredient.

[0002]

2. Description of the Related Art Conventionally, 3-phenyl-1,5-dihydropyrrole-2-one derivatives have been disclosed in, for example, JP-A-4-22.
No. 6957, which is well known, but an N-substituted-4-hydroxy-1,5-dihydropyrrole-2-one derivative in which a hetero atom is directly bonded to a nitrogen atom of a dihydropyrrole ring is completely known. Not.

[0003]

In recent years, some commercially available insecticides have been restricted in use due to problems such as residue, accumulation, and environmental pollution. In addition, the use of the same insecticide for a long time has caused a problem of resistant pests.
Therefore, it is considered that the action is different from commercial insecticides,
Development of insecticides having a novel molecular structure has been desired.

[0004] Also, in the field of herbicides, there is a problem of emergence of resistant weeds, and development of new herbicides having a structure different from that of commercially available herbicides is desired.

The above-mentioned 3-phenyl-1,5-dihydropyrrole-2-one derivative has been developed as such a pesticide, but its activity as a pesticide is inadequate, and the N-type of the present invention is poor. Substituted dihydropyrrole-2-one derivatives overcome this drawback.

The present inventors have conducted intensive studies on dihydropyrrole derivatives. As a result, N-substituted hydroxypyrrole derivatives in which an oxygen atom or a sulfur atom is directly bonded to the nitrogen atom of the dihydropyrrole ring can be used for various insect pests. On the other hand, they have found that they have an extremely excellent insecticidal activity and that they have an excellent herbicidal activity against various weeds, and thus completed the present invention.

[0007]

The present invention provides a compound represented by the following general formula:

[0008]

Embedded image[Wherein, R¹Is a hydrogen atom, C₁~ C₆Alkyl group <
An alkyl group has one C_Three~ C₇Cycloalkyl group, 1
(The phenyl group is a halogen atom and a C
₁~ C₆1 to 5 members selected from the group consisting of alkyl groups
It may be substituted by a substituent. ) One or two C₁~
C₆An alkoxy group (the alkoxy group may have 1 to 5
It may be substituted by a halogen atom. ) One C_Two~
C₆An alkenyloxy group, one (C₁~ C₆Alkoki
C) C₁~ C₆An alkoxy group, one benzyloxy group,
One C₁~ C₆Alkylthio group, 1 to 3 halogens
Atom, one cyano group, one di (C₁~ C₆Alkyl)
An amino group or one 5- or 6-membered heterocyclic group
The ring group has 1 to 4 oxygen, sulfur or nitrogen atoms
Containing a halogen atom and C₁~ C₆Alkyl group
Alkyl groups are substituted by one to three halogen atoms.
May be. 1) or 2 substitutions selected from the group consisting of
May be substituted by a group. Be replaced by｝
No. 》, C_Three~ C₇Cycloalkyl group, C_Two~ C₆Alkene
(The alkenyl group is one to three halogen atoms)
May be replaced by ), C_Two~ C₆Alkynyl group,
Phenyl group (the phenyl group is a halogen atom and a C₁~
C₆1 to 5 positions selected from the group consisting of alkyl groups
It may be substituted by a substituent. ) 5- or 6-membered heterocyclic ring
Group—the heterocyclic group has 1 to 4 oxygen atoms,
Or contains a nitrogen atom and contains one C₁~ C₆Alkyl group (this
The alkyl group is substituted by 1 to 3 halogen atoms
May be. ). ｝, C_Two~ C_Ten
Alkylcarbonyl group (the alkylcarbonyl group is
1 to 3 halogen atoms, 1 C₁~ C₆Alkoxy
Group or one phenoxy group. ),
A benzoyl group (the benzoyl group is a halogen atom and
C₁~ C₆1 to 5 selected from the group consisting of alkyl groups
May be substituted. ), C_Two~ C₈Alkoki
Carbonyl group, di (C₁~ C₆Alkyl) carbamoyl
Group, C₁~ C₆Alkylsulfonyl group or phenylsulfo
A phenyl group (the phenylsulfonyl group is a halogen atom and
And C₁~ C₆1 to 5 selected from the group consisting of alkyl groups
May be substituted. ) And R^Twoas well as
R^ThreeAre the same or different and are a hydrogen atom, C₁~ C₆Archi
Group—the alkyl group has one C_Three~ C₇Cycloalkyl
Group, one phenyl group (the phenyl group is
Atom, C₁~ C₆Alkyl group and C₁~ C₆An alkoxy group
Substituted with 1 to 5 substituents selected from the group consisting of
May be. ) One or two C₁~ C₆Alkoxy group, 1
(C₁~ C₆Alkoxy) C₁~ C₆Alkoxy group, 1
From 13 halogen atoms or one 5- or 6-member
An elementary ring group (the heterocyclic group has 1 to 4 oxygen atoms,
Contains atoms or nitrogen atoms. )
No. ｝, C_Three~ C₇Cycloalkyl group, C_Two~ C₆Alkene
(The alkenyl group is one to three halogen atoms)
May be replaced by ), C_Two~ C₆Alkynyl group,
Phenyl group (the phenyl group is a halogen atom,₁~ C₆
Alkyl group and C₁~ C₆Select from the group consisting of alkoxy groups
It may be substituted by 1 to 5 substituents. )or
Is a 5- or 6-membered heterocyclic group. The heterocyclic group is 1 to 4
Containing two oxygen, sulfur or nitrogen atoms,
Atom and C₁~ C₆Alkyl group (the alkyl group is 1
And may be substituted by up to three halogen atoms. From)
Substituted by one or two substituents selected from the group consisting of
May be. Represents｝, or R^TwoAnd R^ThreeThey combine
Together with the carbon atoms they are
Loalkane, cycloalkene or cycloalkane
Ene ring—the ring is one to three C₁~ C₆Alkyl group,
One C₁~ C₆An alkoxy group, one (C ₁~ C₆Arco
Kishi) C₁~ C₆An alkoxy group, one di (C₁~ C₆Al
Kill) amino group, one C₁~ C_FourAlkylenedioxy group
Or one N- (C₁~ C₆By an alkoxy) imino group
The ring may be substituted at any position with an oxygen atom, a sulfur atom
Or the formula NR⁶A group represented by the formula:⁶Is C₁~ C₆Al
Represents a kill group. ). ｝
Then R^FourIs a hydrogen atom, C_Two~ C_TenAlkylcarbonyl group
(The alkylcarbonyl group has 1 to 3 halogen atoms.
Atom, one C_Two~ C₇Alkylcarbonyloxy group, 1
C₁~ C₆By an alkoxy group or one phenoxy group
May be replaced. ), C_Four~ C₇Cycloalkylcarbo
Nyl group カ ル ボ ニ ル The cycloalkylcarbonyl group is C₁~ C₆
1 selected from the group consisting of an alkyl group and a halogen atom
From 4 substituents, 1 or 2 C₁~ C₆Alkoxy
Group, one or two cyano groups or one phenyl group (the
A phenyl group has one C₁~ C₆Substituted by alkoxy group
May be. ). ｝, C_Three~ C₇A
Alkenylcarbonyl group (the alkenylcarbonyl group
Is substituted by 1 to 3 halogen atoms.
No. ), Benzoyl group ｛the benzoyl group is halogen
Atom and C₁~ C₆An alkyl group (the alkyl group is
Replaced by up to three halogen atoms or one phenoxy group
May be replaced. 1) to 5 pieces selected from the group consisting of
Substituents, 1 to 3 C₁~ C₆An alkoxy group, one C
_Two~ C₇Alkylcarbonyloxy group, one C_Two~ C₇A
Alkoxycarbonyl group, one C₁~ C₆Alkylthio
Group, one C₁~ C₆Alkylsulfinyl group, one C
₁~ C₆Alkylsulfonyl group, 1 phenoxy group, 1
Substituted by one cyano group or one nitro group.
No. {4- to 6-membered heterocyclic carbonyl group}
A rubonyl group is one to four oxygen atoms, sulfur atoms or nitrogen atoms.
Containing 1 to 3 C atoms₁~ C₆Alkyl group (this
The alkyl group is substituted by 1 to 3 halogen atoms
May be. ) 1 to 3 C ₁~ C₆An alkoxy group,
One C₁~ C₆Alkylthio group or one halogen atom
And may be condensed with a benzene ring.
No. ｝, C_Two~ C₈Alkoxycarbonyl group ｛the alcohol
The xycarbonyl group has 1 to 3 halogen atoms, 1
C₁~ C₆An alkoxy group, one C₁~ C₆Alkylthio
Group, one phenyl group (the phenyl group is a halogen atom
Child and C₁~ C₆1 selected from the group consisting of alkyl groups
It may be substituted by up to 5 substituents. ) Or one 5
Or a 6-membered heterocyclic group (the heterocyclic group has 1 to 4
Contains oxygen, sulfur or nitrogen atoms and is a halogen atom
Child and C₁~ C₆One or more selected from the group consisting of alkyl groups
May be substituted by two substituents. Replaced by
May be. ｝, C_Four~ C₇Cycloalkoxycarbonyl
Group, C_Three~ C₇Alkenyloxycarbonyl group, C_Three~ C₇
An alkynyloxycarbonyl group, (C₁~ C₆Alkyl
E) carbonyl group, (phenylthio) carbonyl group
The (phenylthio) carbonyl group is a halogen atom and
C₁~ C₆1 to 5 selected from the group consisting of alkyl groups
May be substituted. ｝, (C₁~ C₆Arco
(Xy) thiocarbonyl group, (phenoxy) thiocarboni
Group—the (phenoxy) thiocarbonyl group is a halogen atom
Atom and C₁~ C₆Selected from the group consisting of alkyl groups
It may be substituted by 1 to 5 substituents. ｝, C_Two~
C₇Alkyldithiocarbonyl group, phenyldithiocal
A bonyl group (the phenyldithiocarbonyl group is
Atom and C₁~ C₆Selected from the group consisting of alkyl groups
It may be substituted by 1 to 5 substituents. ), C₁~
C₆Alkyl group—the alkyl group is one phenyl
Group (the phenyl group is a halogen atom, C₁~ C₆Archi
And C₁~ C₆Selected from the group consisting of alkoxy groups
It may be substituted by 1 to 5 substituents. ), C₁~
C₆An alkoxy group, (C₁~ C₆Alkoxy) C₁~ C₆A
Lucoxy group, C₁~ C₆Alkylthio group, cyano group,
A nonoxy group (the phenoxy group is a halogen atom and a C₁
~ C₆1 to 5 members selected from the group consisting of alkyl groups
It may be substituted by a substituent. ) Or C_Two~ C₇Alkoki
It may be substituted by a cyclocarbonyl group. ｝, C_Two~ C₆A
Lucenyl group, C_Two~ C₆Alkynyl group, di (C₁~ C₆Al
Kill) carbamoyl group ｛in the dialkylcarbamoyl
The two alkyl groups are one with the nitrogen atom to which they are attached.
5- or 6-membered heterocyclic ring (one heterocyclic ring
Contains one oxygen or nitrogen atom in addition to the nitrogen atom
May be. ) May be formed. ｝, J (C₁~ C₆Archi
B) Thiocarbamoyl group ｛the dialkylthiocarbamo
The two alkyl groups in the yl are the nitrogen source to which they are attached.
A 5- or 6-membered heterocyclic ring (the heterocyclic ring
Is one oxygen atom or one nitrogen atom in addition to one nitrogen atom
May be contained. ) May be formed. ｝, C₁~ C₆Al
Killsulfonyl group, phenylsulfonyl group (the phenyl
Rusulfonyl group is a halogen atom and C₁~ C₆Alkyl
With one to five substituents selected from the group consisting of
May be replaced. ) Or di (C₁~ C₆Alkoxy) thiopho
Represents a phoryl group, A is C₁~ C₆Alkyl group
The alkyl group is substituted by 1 to 13 halogen atoms.
May be. ), Halogen atom, C₁~ C₆Alkoxy group
(The alkoxy group is composed of 1 to 5 halogen atoms.
May be replaced. ), C₁~ C₆Alkylthio group, C₁
~ C₆Alkylsulfonyl group, phenyl group (the phenyl
Group is a halogen atom and C₁~ C₆Consists of an alkyl group
Substituted with 1 to 5 substituents selected from the group.
No. ) A 5- or 6-membered heterocyclic group (the heterocyclic group is 1
Containing from 4 to 4 oxygen, sulfur or nitrogen atoms,
Halogen atom and C₁~ C₆Select from the group consisting of alkyl groups
It may be substituted by one or two substituents. ),
Cyano, nitro, amino or phenoxy groups (such as
The phenoxy group is a halogen atom and C₁~ C₆Alkyl group
Substituted with 1 to 5 substituents selected from the group consisting of
May be. ), N represents an integer of 1 to 5, and X
Is an oxygen atom, a sulfur atom, a sulfinyl group or a sulfonyl group.
Represents a hydroxyl group. N-substituted dihydropyrrole derivative represented by
Conductors or salts thereof, pesticides containing it as an active ingredient,
The following general formula which is an intermediate of compound (I)

[0009]

Embedded image [Wherein, R ¹ , R ² , R ³ , A, n and X have the same meanings as described above, and R ⁵ represents a hydrogen atom or a C ₁ -C ₆ alkyl group. And an intermediate of the compound (I) represented by the following general formula:

[0010]

Embedded image [Wherein, R ¹ , R ² , R ³ , A, n, and X represent the same meaning as described above. ] It is an N-substituted amide compound represented by these.

In the present invention, "C ₁ -C ₆ alkyl group"
Is, for example, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl,
Carbon, such as pentyl, 2-methylbutyl, 1-methylpentyl, neopentyl, 1-ethylpropyl, hexyl, 1-methylpentyl, 3,3-dimethylbutyl, 2,2-dimethylbutyl and 1,1-dimethylbutyl A linear or branched alkyl group having 1 to 6 numbers,
It is preferably a linear or branched alkyl group having 1 to 4 carbon atoms (C ₁ -C ₄ alkyl group), more preferably
A straight-chain or branched-chain alkyl group of 1 to 3 carbon atoms (C ₁ -C ₃ alkyl group), more preferably from an alkyl group (C ₁ -C 1 or 2 carbon atoms ₂ alkyl group), and particularly preferably a methyl group.

In the present invention, the "C ₃ -C ₇ cycloalkyl group" is a cycloalkyl group having 3 to 7 carbon atoms such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and cycloheptyl. Preferably, it is a cycloalkyl group having 3 to 6 carbon atoms (C ₃ -C ₆ cycloalkyl group), and more preferably, a cycloalkyl group having 5 or 6 carbon atoms (C ₅
To C ₆ cycloalkyl group), and still more preferably,
A cyclohexyl group.

In the present invention, "halogen" is, for example, chlorine, fluorine, bromine or iodine, preferably chlorine, fluorine or bromine, more preferably chlorine. Atom or fluorine atom, and even more preferably chlorine atom.

In the present invention, "halogen atom and C ₁
-C ₆ phenyl group substituted by 1 to 5 substituents selected from the group consisting of alkyl group ", for example, chlorophenyl, fluorophenyl, bromophenyl, iodophenyl, dichlorophenyl, difluorophenyl,
Chlorofluorophenyl, trichlorophenyl, trifluorophenyl, pentafluorophenyl, methylphenyl, dimethylphenyl, trimethylphenyl, tetramethylphenyl, ethylphenyl, ethylmethylphenyl, propylphenyl, isopropylphenyl, butylphenyl, tert-butylphenyl, pentyl Phenyl,
Phenyl substituted by the same or different 1 to 5 substituents selected from the group consisting of the aforementioned “halogen atom” and the aforementioned “C ₁ -C ₆ alkyl group”, such as hexylphenyl, methylchlorophenyl and methylfluorophenyl A phenyl group substituted by 1 to 3 identical or different substituents selected from the group consisting of a chlorine atom, a fluorine atom, a bromine atom and the above-mentioned “C ₁ -C ₄ alkyl group”. And more preferably a phenyl group substituted by one or two same or different substituents selected from the group consisting of a chlorine atom, a fluorine atom and the above-mentioned “C ₁ -C ₃ alkyl group”, Even more preferably, they are a fluorophenyl group, a chlorophenyl group or a methylphenyl group.

In the present invention, "C ₁ -C ₆ alkoxy group" includes, for example, methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy, tert-butoxy, pentoxy, isopentoxy,
-Methylbutoxy, neopentoxy, 1-ethylpropoxy, hexyloxy, 1-methylpentoxy, 3,3
-Dimethylbutoxy, 1,1-dimethylbutoxy, 1,
A straight-chain or branched-chain alkoxy group having 1 to 6 carbon atoms, such as 2-dimethylbutoxy and 2-ethylbutoxy, preferably a straight-chain or branched chain group having 1 to 4 carbon atoms An alkoxy group (C ₁ -C ₄ alkoxy group), more preferably an alkoxy group having 1 to 3 carbon atoms (C ₁ -C ₃ alkoxy group), and still more preferably a carbon number Is one or two alkoxy groups (C ₁ -C ₂
Alkoxy group), and particularly preferably a methoxy group.

In the present invention, "C ₁ -C ₆ alkoxy group substituted by 1 to 5 halogen atoms" includes, for example, chloromethoxy, 2-chloroethoxy, 3-chloropropoxy, 4-chlorobutoxy, 6-chlorobutoxy, -Chlorohexyloxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, 2-fluoroethoxy, 2,2,2
From 1 to 5 identical or different said "halogen atoms" such as trichloroethoxy, 2,2,2-trifluoroethoxy, 1,1,2,2,2-pentafluoroethoxy and fluorochloromethoxy; The "C
A ₁ -C ₆ alkoxy group ", preferably a said the same or different 1 to 5 chlorine atoms, a fluorine atom or a bromine atom is substituted" C ₁ -C ₄ alkoxy group ", more preferably Is the above-mentioned “C ₁ -C ₃ alkoxy group” substituted by the same or different 1 to 3 chlorine atoms or fluorine atoms, and even more preferably the above-mentioned “C ₁ -alkyl group substituted by 3 fluorine atoms” a -C ₂ alkoxy group ", still more preferably a trifluoromethoxy group or 2,2,2-trifluoroethoxy group.

In the present invention, "C ₂ -C ₆ alkenyloxy" includes, for example, vinyloxy, 2-propenyloxy, 1-methyl-2-propenyloxy, 2-methyl-2-propenyloxy, 2-butenyloxy, A linear or branched alkenyloxy group having 2 to 6 carbon atoms, such as 3-methyl-2-butenyloxy, 1-methyl-2-butenyloxy, 3-butenyloxy, 2-pentenyloxy and 5-hexenyloxy; It is preferably a straight-chain or branched alkenyloxy group having 3 to 6 carbon atoms (C ₃ -C ₆ alkenyloxy group), more preferably a straight-chain having 3 to 5 carbon atoms. or branched-chain alkenyloxy group (C ₃ -C ₅ alkenyloxy group), still more preferably a straight chain having a carbon number of 3 or 4 or branched Arukeniruoki A group (C ₃ -C ₄ alkenyloxy group), particularly preferably a allyloxy group.

In the present invention, "(C₁~ C₆Alkoki
C) C₁~ C₆An "alkoxy group" is, for example, methoxymeth
Xy, methoxyethoxy, methoxypropoxy, methoxy
Sibutoxy, methoxypentyloxy, methoxyhexyl
Luoxy, ethoxymethoxy, ethoxyethoxy, ethoxy
Xypropoxy, isopropoxymethoxy, isopropoxy
Xyethoxy, tert-butoxymethoxy, tert-butoxy
Such as ethoxy and hexyloxyhexyloxy,
One of the "C₁~ C₆The aforementioned alkoxy group is substituted
"C₁~ C₆An alkoxy group ", preferably one
Note "C₁~ C_FourThe aforementioned “C” substituted by “alkoxy group”₁~ C_Four
Alkoxy group ”｛(C₁~ C_FourAlkoxy) C ₁~ C_FourAl
A oxy group｝, and more preferably the aforementioned “C₁~ C_ThreeArco
"C" substituted by "xy group"₁~ C_ThreeAlkoxy group ”｛(C₁
~ C_ThreeAlkoxy) C₁~ C_ThreeAn alkoxy group｝
More preferably, the "C₁~ C_TwoAlkoxy group "
The "C ₁~ C_TwoAlkoxy group '', and even more preferably
Represents a methoxymethoxy group, an ethoxymethoxy group,
It is a ethoxyethoxy group or a 2-ethoxyethoxy group.

In the present invention, “C ₁ -C ₆ alkylthio group” includes, for example, methylthio, ethylthio, propylthio, isopropylthio, butylthio, isobutylthio,
sec-butylthio, tert-butylthio, pentylthio, 2
-Methylbutylthio, 1-methylpentylthio, neopentylthio, hexylthio, 1-methylhexylthio,
A straight-chain or branched-chain alkylthio group having 1 to 6 carbon atoms, such as 3,3-dimethylbutylthio and 2,2-dimethylbutylthio, preferably having 1 to 4 carbon atoms; A straight-chain or branched-chain alkylthio group (C ₁ -C ₄ alkylthio group), more preferably a straight-chain or branched-chain alkylthio group having 1 to 3 carbon atoms (C ₁ -C ₃ alkylthio group) And even more preferably one having 1 carbon atom.
Or two alkylthio groups (C ₁ -C ₂ alkylthio groups), and particularly preferably a methylthio group.

In the present invention, "di (C ₁ -C ₆ alkyl) amino" includes, for example, dimethylamino, diethylamino, dipropylamino, diisopropylamino, dibutylamino and dihexylamino. And the aforementioned “C ₁ -C ₆ alkyl group” is an amino group having two bonds, and preferably, the “C ₁ -C ₄ alkyl group” is 2 amino acids.
An amino group {di (C ₁ -C ₄ alkyl) amino group} which is individually bonded, more preferably an amino group wherein two of the above “C ₁ -C ₃ alkyl groups” are bonded, and even more preferably Is an amino group in which _two of the above “C ₁ -C ₂ alkyl groups” are bonded, and particularly preferably a dimethylamino group.

In the present invention, "5- or 6-membered heterocyclic group (the heterocyclic group contains 1 to 4 oxygen atoms, sulfur atoms or nitrogen atoms)" is, for example, furyl, thienyl, pyrrolyl. , Pyrazolyl, imidazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, tetrazolyl, oxadiazolyl,
Pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl,
Tetrahydrofuranyl, 1,3-dioxolanyl, tetrahydropyranyl, pyrazolinyl, piperazinyl, 1,
A saturated or unsaturated 5- or 6-membered heterocyclic group containing 1 to 4 oxygen, sulfur or nitrogen atoms in the ring, such as 4-dioxanyl, pyrrolidyl, piperidyl and morpholyl; A saturated or unsaturated 5- or 6-membered heterocyclic group containing 1 to 3 oxygen atoms, sulfur atoms or nitrogen atoms in the ring;
Or a saturated or unsaturated 5- or 6-membered heterocyclic group containing two oxygen atoms or nitrogen atoms, and R ¹ , R ² and R
^As a substituent of the alkyl group of ³ , even more preferably, a pyridyl group, a thienyl group, a tetrahydrofuranyl group or a dioxolanyl group, particularly preferably a pyridyl group, a thienyl group or a dioxolanyl group, and most preferably ,
A dioxolanyl group, R ¹ or A is even more preferably a pyridyl group, a thienyl group, a tetrahydrofuranyl group or a dioxolanyl group, particularly preferably a pyridyl group, a thienyl group or a dioxolanyl group, most preferably Is a pyridyl group or a thienyl group, more preferably a 5- or 6-membered heterocyclic group containing one oxygen or nitrogen atom, as R ⁴ , and particularly preferably , A pyridyl group, a thienyl group or a tetrahydrofuranyl group, most preferably a tetrahydrofuranyl group.

In the present invention, “C ₁ -C ₆ alkyl group substituted by 1 to 3 halogen atoms” includes, for example, chloromethyl, bromomethyl, fluoromethyl, trifluoromethyl, iodomethyl, chloroethyl, trifluoroethyl And the above-mentioned "C ₁ -C ₆ alkyl group" substituted by 1 to 3 same or different "halogen atoms", such as chloropropyl, chlorobutyl, chloropentyl and chlorohexyl. or 3 chlorine atoms, wherein the fluorine atom or a bromine atom is substituted is "C ₁ -C ₄ alkyl group", more preferably, the 1 to 3 chlorine atoms or fluorine atom-substituted "C ₁ ~
C ₃ alkyl group ”.

In the present invention, "halogen atom and C ₁
-C ₆ alkyl group (the alkyl group, from 1-3 may. Which is substituted by halogen atoms) 5- or 6-membered heterocyclic group substituted with 1 or 2 substituents selected from the group consisting of '' Is, for example, chloropyridyl, chlorothienyl, chlorotetrahydrofuranyl, chlorodioxolanyl, dichloropyridyl, dichlorothienyl, dichlorodioxolanyl, fluoropyridyl, fluorothienyl, fluorodioxolanyl, difluoropyridyl, difluorooxolanyl, Bromopyridyl, bromothienyl, bromodioxolanyl, dibromopyridyl, iodopyridyl, methylpyridyl, dimethylpyridyl, ethylpyridyl, propylpyridyl, isopropylpyridyl,
Said "halogen atom", such as butylpyridyl, tert-butylpyridyl, pentylpyridyl, hexylpyridyl, methylthienyl, ethylthienyl, dimethylthienyl, methyldioxolanyl, dimethyldioxolanyl, chloromethylpyridyl and trifluoromethylpyridyl , The “C ₁ -C ₆ alkyl group” and the “1 to 3”
Was chosen same or different from the group consisting of C ₁ -C ₆ alkyl group "substituted by halogen atoms 1 or 2
And the above-mentioned "5- or 6-membered heterocyclic group (the heterocyclic group contains 1 to 4 oxygen, sulfur or nitrogen atoms)", preferably chlorine. selected atom, a fluorine atom, a bromine atom, from the group consisting of the "C ₁ -C ₄ alkyl group" and "1 to 3 chlorine atoms, C ₁ -C ₄ alkyl group substituted by a fluorine atom or a bromine atom." A saturated or unsaturated 5- or 6-membered heterocyclic group containing 1 to 3 oxygen atoms or nitrogen atoms in the ring, which is substituted with one or two same or different substituents, and more preferably the chlorine atom, a fluorine atom, the "C ₁
1 or 2 same or different substituents selected from the group consisting of -C ₃ alkyl group ”and“ C ₁ -C ₃ alkyl group substituted by ₁ to ₃ chlorine atoms or fluorine atoms ” A saturated or unsaturated 5- or 6-membered heterocyclic group containing one or two oxygen or nitrogen atoms in the ring, and still more preferably a chlorine atom, a fluorine atom, a methyl group and an ethyl group A pyridyl group, a thienyl group or a dioxolanyl group substituted by one or two identical or different substituents selected from the group consisting of:

The R of the present invention¹In "one C_Three~ C₇
A cycloalkyl group, one phenyl group (the phenyl group
Is a halogen atom and C₁~ C₆Group consisting of alkyl groups
Substituted with 1 to 5 substituents selected from
No. ) One or two C₁~ C₆Alkoxy group (the
Coxy groups are substituted by 1 to 5 halogen atoms.
May be. ) One C_Two~ C₆Alkenyloxy group, 1
(C₁~ C₆Alkoxy) C₁~ C₆One alkoxy group
Benzyloxy group, one C₁~ C₆Alkylthio group,
1 to 3 halogen atoms, 1 cyano group, 1 diamine
(C₁~ C₆Alkyl) amino group or one 5 or 6
Membered heterocyclic group (the heterocyclic group has 1 to 4 oxygen atoms,
Containing a sulfur atom or a nitrogen atom, a halogen atom and C₁
~ C₆One or two selected from the group consisting of alkyl groups
It may be substituted by a substituent. C) substituted by₁
~ C₆An `` alkyl group '' is, for example, cyclopropylmethyl
, Cyclohexylmethyl, cyclohexylbutyl,
Benzyl, (4-chlorophenyl) methyl, (4-methyl
Phenyl) methyl, phenylbutyl, methoxymethyl,
Ethoxymethyl, propoxymethyl, butoxymethyl,
Methoxyethyl, ethoxyethyl, butoxyethyl,
Toxipropyl, methoxyethyl, methoxybutyl,
α, α-dimethoxymethyl, α, α-diethoxymethyl
, 2,2,2-trifluoroethoxymethyl, α,
α, α-trifluoromethyl, allyloxymethyl, 2
-Butenyloxymethyl, methoxyethoxymethyl,
Toxiethoxymethyl, benzyloxymethyl, methyl
Thiomethyl, ethylthiomethyl, chloromethyl, 2-c
Loroethyl, cyanomethyl, 1-cyanoethyl, 4-cy
Anobutyl, dimethylaminomethyl, 2-pyridylmethy
, 3-pyridylmethyl, 2-thienylmethyl, 1-pi
Lazolylmethyl, 1-imidazolylmethyl, 2-tetra
Of hydrofuranylmethyl and 2-dioxolanylmethyl
One such "C_Three~ C₇Cycloalkyl group ", 1
Phenyl groups, one of the aforementioned “halogen atoms and C₁~
C₆1 to 5 positions selected from the group consisting of alkyl groups
A phenyl group substituted by a substituent ", the same or different
One or two of the above “C₁~ C₆Alkoxy group ", the same or
1 or 2 different “1 to 5 halogen atoms”
C substituted by₁~ C₆Alkoxy group ", one of the above
"C_Two~ C₆An alkenyloxy group ”and one of the above“ (C₁
~ C₆Alkoxy) C₁~ C₆Alkoxy group "
And the above-mentioned “C”₁~ C₆Alkylthio
1 to 3 identical or different “halogen atoms”
Offspring, one cyano group and one of the aforementioned “di (C₁~ C₆Al
A) a) 5- or 6-membered heterocyclic ring
Group (the heterocyclic group is one to four oxygen atoms, sulfur atoms
Or contains a nitrogen atom. ) ”Or one of the above“ halogens ”
Atom and C₁~ C₆Selected from the group consisting of alkyl groups
5- or 6-membered compound substituted by one or two substituents
The above-mentioned “C” substituted by₁~ C₆Alkyl group ''
Preferably, one of the "C_Three~ C₇Cycloalkyl
Group, one phenyl group, one chlorine atom, fluorine atom
Child, bromine atom and C₁~ C_FourSelect from the group consisting of alkyl groups
1 to 3 identical or different substituents substituted
Phenyl group ", one or two of the same or different" C
₁~ C_FourAn alkoxy group ", one or two identical or different
"Selected from the group consisting of chlorine, fluorine and bromine
Substituted with 1 to 5 identical or different substituents
Done C₁~ C_FourAn alkoxy group "and one of the aforementioned" C_Three~ C_Five
An alkenyloxy group ”and one of the above“ (C₁~ C_FourArco
Kishi) C ₁~ C_FourAlkoxy group ", one benzyloxy
Group, one of the above “C₁~ C_FourAlkylthio group ", 1 to 3
Chlorine, fluorine or bromine atoms, one
An ano group, one of the above “di (C₁~ C_FourAlkyl) amino
Group ", one" 5- or 6-membered heterocyclic group (the heterocyclic group
Contains one to three oxygen, sulfur or nitrogen atoms.
Have. ) "Or one" chlorine, fluorine, bromine
Atom and C₁~ C_FourAn alkyl group selected from the group consisting of
One or two substituents substituted by one or different
Contains from 3 to 3 oxygen, sulfur or nitrogen atoms
Saturated or unsaturated 5- or 6-membered heterocyclic group "
The "C₁~ C_FourAlkyl group ", more preferably 1
"C_Three~ C₆Cycloalkyl group ", one phenyl
Group, one chlorine atom, fluorine atom and C₁~ C_ThreeAl
The same or different 1 or selected from the group consisting of
A phenyl group substituted by two substituents ", the same or different
One or two of the above “C₁~ C_ThreeAlkoxy group "
Are different 1 or 2 "same or different 1 or 3
Substituted by a chlorine or fluorine atom of₁~ C_ThreeA
Alkoxy group ”and one of the aforementioned“ C_Three~ C_FourAlkenyloxy
Group) and one of the above "(C₁~ C_ThreeAlkoxy) C₁~ C_ThreeA
Alkoxy group '', one benzyloxy group, one
"C₁~ C_ThreeAlkylthio group ", the same or different
Three chlorine or fluorine atoms, one cyano group,
One of the aforementioned "di (C₁~ C_ThreeAlkyl) amino group ”, one
"5- or 6-membered heterocyclic group (the heterocyclic group is 1 to
Contains two oxygen or nitrogen atoms. ) "Or one
"Chlorine atom, fluorine atom and C₁~ C_ThreeFrom an alkyl group
1 or 2 identical or different substitutions selected from the group consisting of
One or two oxygen or nitrogen atoms in the ring, substituted by a group
Or a saturated or unsaturated 5- or 6-membered heterocyclic group containing
"C₁~ C_ThreeAlkyl group ".

In the present invention, "C ₂ -C ₆ alkenyl group" includes, for example, vinyl, 2-chlorovinyl, 2-propenyl, 2-chloro-2-propenyl, 3-chloro-2
-Propenyl, 3,3-dichloro-2-propenyl, 1
-Methyl-2-propenyl, 2-methyl-2-propenyl, 1-butenyl, 2-butenyl, 3-methyl-2-butenyl, 1-methyl-2-butenyl, 3-butenyl, 1
-Pentenyl, 2-pentenyl, 1-hexenyl and 5
A straight-chain or branched alkenyl group having 2 to 6 carbon atoms, such as -hexenyl, preferably having 3 carbon atoms.
To 5 linear or branched alkenyl groups (C ₃ -C ₅
Alkenyl group), preferably a straight-chain or branched-chain alkenyl group having 3 or 4 carbon atoms (C ₃ -C ₄ alkenyl group), more preferably a 2-propenyl group.

In the present invention, the "C ₂ -C ₆ alkenyl group substituted by 1 to 3 halogen atoms" includes, for example, 3-chloro-2-propenyl, 3,3-dichloro-
2-propenyl, 3-fluoro-2-propenyl, 3,
3-difluoro-2-propenyl, 4,4-dichloro-
Like 3-butenyl, 5,5-dichloro-4-pentenyl and 4,5,5-trifluoro-4-pentenyl,
1 to 3 identical or different “halogen atoms” are substituted “C ₂ -C ₆ alkenyl groups”, preferably 1 to 3 identical or different chlorine, fluorine or bromine atoms; The above-mentioned “C ₃ -C ₅ alkenyl group” in which an atom is substituted, more preferably 1 or 2 identical or different
"C ₃ -C ₄ substituted with two chlorine atoms or fluorine atoms
Alkenyl group ", and even more preferably a propenyl group substituted by one or two chlorine atoms.

In the present invention, "C_Two~ C₆Alkynyl
“Group” is, for example, ethynyl, 2-propynyl, 1-methyl
Lupropynyl, 2-butynyl, 2-pentynyl, 2-he
Having 2 to 2 carbon atoms, such as xynyl and 5-hexynyl;
6 linear or branched alkynyl groups, preferably
A linear or branched alkynyl group having 3 to 5 carbon atoms (C
_Three~ C_FiveAlkynyl group), and more preferably the carbon number is
3 or 4 linear or branched alkynyl groups (C_Three~ C_FourA
Alkynyl group), and even more preferably, 2-propynyl.
Group.

In the present invention, “5 or 6 substituted by one C ₁ -C ₆ alkyl group (the alkyl group may be substituted by 1 to 3 halogen atoms)”.
"Membered heterocyclic group" is, for example, 5-methyl-2-furanyl,
5-methyl-2-thienyl, 4-methyl-2-oxazolyl, 5-methyl-2-thiazolyl, 3-methyl-5
Isoxazolyl, 6-methyl-2-pyridyl, 6-methyl-3-pyridyl, 6-trifluoromethyl-3-pyridyl, 5-trifluoromethyl-2-pyridyl, 5-
Methyl-2-pyrimidinyl, 5-methyl-2-pyrazinyl, 5-methyl-2-pyridazinyl, 4-methyl-2-
Such as tetrahydrofuranyl and 5-methyl-2-tetrahydropyranyl, C ₁ is substituted by one of the "C ₁ -C ₆ alkyl group" or one of the "1 to 3 halogen atoms -C _And the above-mentioned "5- or 6-membered heterocyclic group (the heterocyclic group contains 1 to 4 oxygen atoms, sulfur atoms or nitrogen atoms)" substituted with " ₆ alkyl groups". "C ₁ -C ₄ alkyl group" substituted by _one "C ₁ -C ₄ alkyl group substituted by one to three chlorine, fluorine or bromine atoms" A saturated or unsaturated 5- or 6-membered heterocyclic group containing three oxygen atoms, sulfur atoms or nitrogen atoms ”, more preferably one of the above-mentioned“ C ₁ -C ₃ alkyl groups ”or 1 Substituted by one to three chlorine or fluorine atoms A saturated or unsaturated 5- or 6-membered heterocyclic group containing one or two oxygen atoms or nitrogen atoms in the ring, which is substituted with a substituted or unsubstituted C ₁ -C ₃ alkyl group. It is a trifluoromethylpyridyl group or a thienyl group.

In the present invention, "C ₂ -C ₁₀ alkylcarbonyl group" includes, for example, acetyl, propionyl, propylcarbonyl, isopropylcarbonyl, butylcarbonyl, sec-butylcarbonyl, isobutylcarbonyl, tert-butylcarbonyl, pentylcarbonyl, Pentyl-2-carbonyl, 2,2-dimethyl-1
A carbonyl group to which a linear or branched alkyl group having 1 to 9 carbon atoms such as propylcarbonyl, hexylcarbonyl, heptylcarbonyl, octylcarbonyl and nonylcarbonyl is bonded;
It is a carbonyl group (C ₂ -C ₈ alkylcarbonyl group) to which a linear or branched alkyl group having 1 to 7 carbon atoms is bonded, and more preferably a straight-chain having 1 to 5 carbon atoms. A carbonyl group (C ₂ -C ₆ alkylcarbonyl group) to which a chain or branched alkyl group is bonded, and even more preferably, a linear or branched alkyl group having 1 to 4 carbon atoms is bonded. Carbonyl group (C ₂ -C ₅ alkylcarbonyl group), particularly preferably 2,2-dimethylpropionyl group, 2,2-dimethylbutyryl group, 3,3
-A dimethylbutyryl group or an acetyl group.

In R ¹ of the present invention, “a C ₂ -C ₁₀ alkylcarbonyl group substituted by one to three halogen atoms, one C ₁ -C ₆ alkoxy group or one phenoxy group” is For example, methoxyacetyl, ethoxyacetyl, isopropoxyacetyl, phenoxyacetyl,
The same or like, such as 3-phenoxypropionyl, chloroacetyl, trichloroacetyl, trifluoroacetyl, 3-chloropropionyl, 2,2-dimethyl-3-chloropropionyl, 2-chloro-2-methylpropionyl and 2-methoxynonyl 1 to 3 different “halogen atoms”, 1 “C ₁ -C ₆ alkoxy group” or “C ₂ -C substituted with 1 phenoxy group”
₁₀ alkylcarbonyl group '', preferably 1 to 3 identical or different chlorine atoms, fluorine atoms or bromine atoms, one of the above-mentioned 'C ₁ -C ₄ alkoxy groups' or one phenoxy group. substituted wherein a "C ₂ -C ₈ alkylcarbonyl group", more preferably, the same or different 1
To 3 chlorine atoms or fluorine atom, is said one said of the "C ₁ -C ₃ alkoxy group" or the one phenoxy group is substituted "C ₂ -C ₆ alkylcarbonyl group",
Even more preferably, the above-mentioned “C ₂ -C ₅ alkylcarbonyl group” substituted by one phenoxy group.

In the present invention, "a benzoyl group substituted by one to five halogen atoms or one C ₁ -C ₆ alkyl group" is, for example, chlorobenzoyl, dichlorobenzoyl, trichlorobenzoyl, fluorobenzoyl, difluoro Benzoyl, trifluorobenzoyl,
1 to 5 identical or different, such as pentafluorobenzoyl, bromobenzoyl, iodobenzoyl, chlorofluorobenzoyl, methylbenzoyl, ethylbenzoyl, propylbenzoyl, isopropylbenzoyl, butylbenzoyl, tert-butylbenzoyl, pentylbenzoyl and hexylbenzoyl Benzoyl groups to which one of the above “halogen atoms” or one of the above “C ₁ -C ₆ alkyl groups” are bonded, preferably 1 to 3 identical or different chlorine, fluorine or bromine atoms Or a benzoyl group to which _one “C ₁ -C ₄ alkyl group” is bonded, more preferably one or two chlorine atoms or fluorine atoms, or one “C ₁ -C ₃ alkyl group” Is an attached benzoyl group, even more preferably chlorobenzoy Is a group or a methyl benzoyl group.

In the present invention, "C ₂ -C ₈ alkoxycarbonyl group" includes, for example, methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, butoxycarbonyl, sec-butoxycarbonyl, isobutoxycarbonyl, cyclobutoxycarbonyl, tert-butoxycarbonyl Pentoxycarbonyl, pentyl-2-oxycarbonyl, 2,2-dimethylpentyl-1-oxycarbonyl, pentyl-3-oxycarbonyl, hexyloxycarbonyl, 1,2-dimethylpropoxycarbonyl, 1,2,2-trimethyl A carbonyl group (C ₂ -C ₈ alkoxycarbonyl group) to which a linear or branched alkoxy group having 1 to 7 carbon atoms such as propoxycarbonyl and 1-isopropyl-2-methylpropoxycarbonyl is bonded. More preferably, it is a carbonyl group (C ₂ -C ₅ alkoxycarbonyl group) to which a straight-chain or branched-chain alkoxy group having 1 to 4 carbon atoms is bonded, and more preferably 1 to 4 carbon atoms. A carbonyl group (C ₂ -C ₄ alkoxycarbonyl group) to which three straight or branched chain alkoxy groups are bonded, and even more preferably a carbonyl group to which an alkoxy group having 1 or 2 carbon atoms is bonded. Group (C ₂ -C ₃ alkoxycarbonyl group), particularly preferably a methoxycarbonyl group.

In the present invention, “di (C)₁~ C₆Archi
L) carbamoyl group ”is, for example, dimethylaminocarbyl
Bonyl, diethylaminocarbonyl, dipropyl
Minocarbonyl group, diisopropylaminocarbonyl
Group, dibutylaminocarbonyl group and dihexylamino
Two identical or different, such as carbonyl groups,
"C ₁~ C₆Carbamoy with "alkyl" attached to the nitrogen atom
And preferably two identical or different
"C₁~ C_FourCarbamoy with "alkyl" attached to the nitrogen atom
｛基 ｛（C₁~ C_FourAlkyl) carbamoyl group｝
More preferably, two identical or different “C₁
~ C_ThreeA carbamoyl group in which "alkyl" is bonded to a nitrogen atom
Page (C₁~ C_ThreeAlkyl) carbamoyl group 、
More preferably, two identical or different “C₁~
C_TwoA carbamoyl group in which "alkyl" is bonded to a nitrogen atom
Page (C₁~ C_TwoAlkyl) carbamoyl group｝
More preferably, it is a dimethylcarbamoyl group.

In the present invention, "C₁~ C₆Alkylsul
"Honyl group" is, for example, methylsulfonyl, ethylsulfonyl
Honyl, isopropylsulfonyl, propylsulfoni
Butylsulfonyl, pentylsulfonyl and hexyl
Straight chain having 1 to 6 carbon atoms, such as rusulfonyl
Or a branched alkylsulfonyl group;
Linear or branched alkyl sulfo having 1 to 4 prime numbers
Nyl group (C₁~ C_FourAlkylsulfonyl group)
Preferably, a linear or branched chain having 1 to 3 carbon atoms is used.
Rukylsulfonyl group (C₁~ C_ThreeAlkylsulfonyl group)
And still more preferably 1 or 2 carbon atoms
A linear or branched alkylsulfonyl group (C ₁~ C_TwoArchi
And particularly preferably methylsulfonyl group).
Nyl group.

In the present invention, “phenylsulfonyl group substituted by 1 to 5 halogen atoms or 1 C ₁ -C ₆ alkyl group” includes, for example, chlorophenylsulfonyl, dichlorophenylsulfonyl, trichlorophenylsulfonyl, fluorophenyl Sulfonyl, difluorophenylsulfonyl, trifluorophenylsulfonyl, pentafluorophenylsulfonyl, bromophenylsulfonyl, iodophenylsulfonyl, chlorofluorophenylsulfonyl, methylphenylsulfonyl, ethylphenylsulfonyl, propylphenylsulfonyl, isopropylphenylsulfonyl, butylphenylsulfonyl, tert -The same or similar, such as butylphenylsulfonyl, pentylphenylsulfonyl and hexylphenylsulfonyl Is a phenylsulfonyl group substituted by 1 to 5 different “halogen atoms” or 1 “C ₁ -C ₆ alkyl group”, preferably 1 to 3 chlorine atoms which are the same or different An atom, a fluorine atom or a bromine atom or a phenylsulfonyl group substituted by one of the “C ₁ -C ₄ alkyl groups”, more preferably 1 to 3 identical or different chlorine or fluorine atoms or The “C ₁ -C ₃ alkyl group” is a substituted phenylsulfonyl group, even more preferably, one or two same or different chlorine or fluorine atoms or the “C ₁ -C ₂ alkyl group” Is a substituted phenylsulfonyl group.

In R ² , R ³ and R ⁴ of the present invention, “substituted by 1 to 5 substituents selected from the group consisting of a halogen atom, a C ₁ -C ₆ alkyl group and a C ₁ -C ₆ alkoxy group” A phenyl group '' is, for example, chlorophenyl,
Fluorophenyl, bromophenyl, iodophenyl,
Dichlorophenyl, difluorophenyl, chlorofluorophenyl, trichlorophenyl, trifluorophenyl, perfluorophenyl, methylphenyl, dimethylphenyl, trimethylphenyl, tetramethylphenyl, ethylphenyl, ethylmethylphenyl, propylphenyl, isopropylphenyl, butylphenyl, te
The “halogen atom”, the “C ₁ -C ₆ alkyl group "and the" C ₁ ~
A phenyl group substituted by the same or different 1 to 5 substituents selected from the group consisting of "C ₆ alkoxy group", preferably a chlorine atom, a fluorine atom, a bromine atom, and the above-mentioned "C ₁ -C ₄ The same or different 1 to 3 groups selected from the group consisting of an "alkyl group" and the "C ₁ -C ₄ alkoxy group"
Are substituted phenyl groups, and are more preferably selected from the group consisting of chlorine atoms, fluorine atoms, the aforementioned “C ₁ -C ₃ alkyl groups” and the aforementioned “C ₁ -C ₃ alkoxy groups”. 1 or 2 identical or different phenyl groups substituted by 1 or 2 substituents, and even more preferably 1 or 2 identical or different ones selected from the group consisting of chlorine, fluorine, methyl and methoxy Is a substituted phenyl group.

In R ² and R ³ of the present invention, “one C
₃ -C ₇ cycloalkyl group, one phenyl group (said phenyl group, a halogen atom, C ₁ -C ₆ alkyl and C ₁
It may be substituted by 1 to 5 substituents selected from the group consisting of a C ₆ alkoxy group. ) One or two C ₁
-C ₆ alkoxy group, one (C ₁ -C ₆ alkoxy) C ₁
By a C ₆ alkoxy group, 1 to 13 halogen atoms or one 5 or 6 membered heterocyclic group (the heterocyclic group contains 1 to 4 oxygen, sulfur or nitrogen atoms). “Substituted C ₁ -C ₆ alkyl group” is, for example, cyclopropylmethyl, cyclopropylethyl, cyclohexylmethyl, benzyl, 1-phenylethyl,
1-phenylpropyl, 2-phenylethyl, 4-phenylbutyl, chlorobenzyl, bromobenzyl, fluorobenzyl, dichlorobenzyl, difluorobenzyl,
Perchlorobenzyl, methylbenzyl, dimethylbenzyl, trimethylbenzyl, tetramethylbenzyl. Methoxybenzyl, methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl, dimethoxyethyl, hexyloxymethyl, methoxymethoxymethyl, methoxymethoxyethyl, methoxyethoxymethyl, methoxyethoxyethyl, ethoxymethoxymethyl, ethoxymethoxyethyl, ethoxyethoxymethyl, 1 such as ethoxyethoxyethyl, trifluoromethyl, 2,2,2-trifluoroethyl, perfluorohexyl, 1,3-dioxan-2-ylmethyl, 1,3-dioxan-2-ylethyl, tetrahydrofuranylmethyl number of the "C ₃ -C ₇ cycloalkyl group", one phenyl group,
One of the aforementioned “halogen atom, C ₁ -C ₆ alkyl group and C 1
A phenyl group substituted with 1 to 5 substituents selected from the group consisting of ₁ to ₆ alkoxy groups, 1 or 2 identical or different 1 to 2 C _{1 to} C ₆ alkoxy groups, The aforementioned “(C ₁ -C ₆ alkoxy) C ₁ -C ₆ alkoxy group”, the same or different 1 to 13 “halogen atoms” or one “5 or 6-membered heterocyclic group (the heterocyclic ring groups, 1 to 4 oxygen atoms, a sulfur atom or a nitrogen atom.) the substituted by "" C ₁ -C ₆
Alkyl group ", preferably, one of the" C ₃ -C ₇
Cycloalkyl group ", one phenyl group, one of the" chlorine atom, a fluorine atom, a bromine atom, and the same or different selected from C ₁ -C ₄ alkyl and C ₁ -C ₄ group consisting alkoxy group 1 1 to 2 identical or different “C ₁ -C ₄ alkoxy groups” and one identical “(C ₁ -C ₄ alkoxy) C
₁ -C ₄ alkoxy group ", the same or different 1 to 5 chlorine atoms, fluorine atom or bromine atom or one of the" 1 to 3 oxygen atoms in the ring, saturated or containing sulfur atom or nitrogen atom is said substituted by non 5 or 6 membered heterocyclic group, saturated, "" C ₁ -C ₄ alkyl group ", more preferably, one of the" C ₃ -C ₃ cycloalkyl group ", 1
Phenyl groups, one "chlorine atom, fluorine atom, C ₁
A phenyl group substituted by the same or different one or two substituents selected from the group consisting of a C ₁ -C ₃ alkyl group and a C ₁ -C ₃ alkoxy group,
"C ₁ -C ₃ alkoxy groups" and one "(C
₁ -C ₃ alkoxy) C ₁ -C ₃ alkoxy group "saturated containing the same or different 1 to 3 chlorine atoms or fluorine atoms or one" 1 or 2 oxygen atoms or nitrogen atoms in the ring or said substituted by non 5 or 6 membered heterocyclic group, saturated "is" C ₁ -C ₃ alkyl group ", further preferably more, cyclohexylmethyl, benzyl, chlorobenzyl, methylbenzyl, methoxybenzyl, methoxymethyl An ethyl, methoxyethoxyethyl or trifluoromethyl group.

In the present invention, "mono (C ₁ -C ₆ alkyl) amino" means, for example, monomethylamino, monoethylamino, monopropylamino, monoisopropylamino, monobutylamino and monohexyl. An amino group such as an amino group to which one of the aforementioned “C ₁ -C ₆ alkyl groups” is bonded, and preferably an amino group of which _one of the aforementioned “C ₁ -C ₄ alkyl groups” is bonded {mono ( a C ₁ -C ₄ alkyl) amino group}, more preferably, the "C ₁ ~
The “C ₃ alkyl group” is an amino group having one bond, and even more preferably, the “C ₁ -C ₂ alkyl group” is an amino group having one bond, and particularly preferably a monomethylamino group. is there.

In the present invention, a “4- to 7-membered cycloalkane, cycloalkene or cycloalkanediene ring—in the ring, at any position, a ring represented by an oxygen atom, a sulfur atom or a group represented by the formula NR ⁶ ( Embedded image wherein R ⁶ represents a C ₁ -C ₆ alkyl group.) “” Is, for example, cyclobutane, cyclopentane, cyclohexane, cycloheptane, tetrahydrofuran, tetrahydropyran, tetrahydrothiopyran 4- to 7-membered cycloalkyls such as N-methylpiperazine, cyclohexene, cyclopentene, oxolane, 1,3-dioxolane, 1,3-dithiolane and the 5,6-dihydro-4H- [1,3] oxazine ring. An alkane, cycloalkene or cycloalkanediene ring wherein any carbon atom on the ring is oxygen Child, a group represented by a sulfur atom or the formula NR ⁶ is also good ring, preferably, a 4 to 7-membered cycloalkane, cycloalkene or cycloalkane diene ring {the ring is an arbitrary position Wherein the ring is an oxygen atom, a sulfur atom or a group represented by the formula NR ⁶ (wherein R ⁶ is
It represents a C ₁ -C ₄ alkyl group. ). And more preferably a 4- to 6-membered cycloalkane, cycloalkene or cycloalkanediene ring. は The ring may have an oxygen atom, a sulfur atom or a group represented by the formula NR ⁶ at any position. (Wherein R ⁶ represents a C ₁ -C ₃ alkyl group). ｝,
Even more preferably, it is a cyclohexane ring.

In the present invention, “C ₁ -C ₄ alkylenedioxy group” refers to methylenedioxy, ethylenedioxy,
A linear alkylenedioxy group having 1 to 4 carbon atoms, such as a trimethylenedioxy or tetramethylenedioxy group, preferably a methylenedioxy group, an ethylenedioxy group or a trimethylenedioxy group; An oxy group, more preferably an ethylenedioxy group or a trimethylenedioxy group.

In the present invention, "N- (C ₁ -C ₆ alkoxy) imino group" is, for example, N-methoxyimino or N-methoxyimino.
An ethoxyimino, N-propoxyimino, N-isopropoxyimino, N-butoxyimino, N-pentyloxyimino or N-hexyloxyimino group,
The “C ₁ -C ₆ alkoxy group” is an imino group bonded to a nitrogen atom, and preferably, the “C ₁ -C ₄ alkoxy group” is an imino group {N- (C _1- C ₄ alkoxy) imino group 、, and more preferably the aforementioned “C
₁ -C ₃ alkoxy group "is an imino group attached to the nitrogen atom {N- (C _{1 ~C 3} alkoxy) imino group}, still more preferably, the" C ₁ -C ₂ alkoxy group "is nitrogen An imino group {N- (C ₁ -C ₂ alkoxy) imino group} bonded to an atom.

The R of the present invention^TwoAnd R^ThreeIn "1 to 3
C₁~ C₆Alkyl group, one C ₁~ C₆Alkoxy
Group, one (C₁~ C₆Alkoxy) C₁~ C₆Alkoxy
Group, one di (C₁~ C₆Alkyl) amino group, one C
₁~ C_FourAn alkylenedioxy group or one N- (C₁~ C₆
4- to 7-membered substituted by an (alkoxy) imino group,
Cycloalkane, cycloalkene or cycloalka
Ndiene ring '' is, for example, 3-methylcyclopentane,
3-methoxycyclopentane, 3,4-dimethylcyclo
Pentane, 2-methylcyclohexane, 3-methylcycline
Hexane, 4-methylcyclohexane, 3,5-dimethyl
Tylcyclohexane, 4-ethylcyclohexane, 4-
Propylcyclohexane, 4-butylcyclohexane,
4-methoxycyclohexane, 4-ethoxycyclohexyl
Sun, 4-methoxymethoxycyclohexane, 4-etho
Xymethoxycyclohexane, 4-methoxyethoxy
Clohexane, 4-ethoxyethoxycyclohexane,
4-dimethylaminocyclohexane, 4,4-ethylene
Dioxycyclohexane, 4,4-trimethylene dioxy
Cyclohexane, 4- (N-methoxyimino) cyclo
Hexane, 4- (N-ethoxyimino) cyclohexa
4-methyl-3-cyclohexene, 4-methyl-2
-Cyclohexene, 3,4-dimethyl-2-cyclopen
Ten, 2-methyltetrahydropyran, 2,6-dimethyl
Rutetrahydropyran, 1,2-dimethylpiperazine,
2-methyl-1,3-dioxolane and 2-methyltet
1 to 3 identical or different, such as lahydrofuran
"C₁~ C₆Alkyl group "and one of the aforementioned" C₁~ C₆
Alkoxy group "and one of the above-mentioned" (C₁~ C₆Alkoxy)
C₁~ C₆An alkoxy group ”and one of the aforementioned“ di (C₁~ C₆A
Alkyl) amino group ”and one of the above“ C₁~ C_FourAlkylenedi
An oxy group ”or one of the above“ N- (C₁~ C₆Alkoki
(4) the above-mentioned "4- to 7-membered" substituted by
Cycloalkane, cycloalkene or cycloalka
N-diene ring: In this ring, at any position, the ring is an oxygen atom or sulfur
Yellow atom or formula NR⁶A group represented by the formula:⁶Is C₁~
C₆Represents an alkyl group. )
No. ｝ ”, Preferably 1 to 3 identical or different
"C₁~ C_FourAlkyl group ”or one of the above“ C₁
~ C_FourAlkoxy group "and the" (C₁~ C_FourAlkoxy)
C₁~ C_FourAlkoxy group "and the aforementioned" di (C₁~ C_FourArchi
L) amino group ", methylenedioxy group, ethylenedioxy
シ, trimethylenedioxy group or the above “N- (C
₁~ C_FourSubstituted by an (alkoxy) imino group "
A 7-membered saturated ring, more preferably 1 or 2
"C₁~ C_ThreeAlkyl group ”or one of the above“ C₁~ C_ThreeAl
Coxy group "and" (C₁~ C _ThreeAlkoxy) C₁~ C_ThreeA
Alkoxy group ”and the aforementioned“ di (C₁~ C_ThreeAlkyl) amino
Group ", ethylenedioxy group, trimethylenedioxy group
Or "N- (C₁~ C_ThreeAlkoxy) imino group "
A more substituted 4- to 6-membered saturated ring, even more preferred
Has one or two of the above-mentioned "C₁~ C_TwoAlkyl group "or 1
"C₁~ C_TwoAlkoxy group "and the" (C₁~ C_Two
Alkoxy) C₁~ C_TwoAlkoxy group ", ethylene dioxy
シ, trimethylenedioxy group or the above “N- (C
₁~ C_TwoSubstituted by an (alkoxy) imino group "
A hexane ring, particularly preferably one of the above-mentioned “C₁~
C_TwoAlkoxy group ", ethylenedioxy group, trimethylene
Dioxy group or the aforementioned “N- (C₁~ C_TwoAlkoxy) i
A cyclohexane ring substituted by `` amino group ''
Is also preferably a methoxycyclohexane ring.

In the present invention, “C ₂ -C ₇ alkylcarbonyloxy group” includes, for example, acetyloxy, propionyloxy, propylcarbonyloxy, isopropylcarbonioxyl, butylcarbonyloxy, sec.
-Butylcarbonyloxy, isobutylcarbonyloxy, tert-butylcarbonyloxy, pentylcarbonyloxy, pentyl-2-carbonyloxy, 2,2-
A carbonyloxy group to which a linear or branched alkyl group having 1 to 6 carbon atoms such as dimethyl-1-propylcarbonyloxy and hexylcarbonyloxy is bonded, preferably 1 to 6 carbon atoms; A carbonyloxy group (C ₂ -C ₅ alkylcarbonyloxy group) to which four linear or branched alkyl groups are bonded, more preferably a linear or branched chain having 1 to 3 carbon atoms Is a carbonyloxy group (C ₂ -C ₄ alkylcarbonyloxy group) having an alkyl group bonded thereto, and still more preferably,
Acetyloxy group.

In R ⁴ of the present invention, “substituted by one to three halogen atoms, one C ₂ -C ₇ alkylcarbonyloxy group, one C ₁ -C ₆ alkoxy group or one phenoxy group” C ₂ -C ₁₀ alkylcarbonyl group ”
Is, for example, chloropropionyl, methyl-chloropropionyl, dimethyl-chloropropionyl, dimethyl-
1 to 3 identical or different said "halogen atoms", such as acetoxypropionyl, methoxyacetyl, ethoxyacetyl, methyl-methoxypropionyl, methyl-ethoxypropionyl, methyl-methoxybutanoyl and phenoxyacetyl; a "C ₂ -C ₇ alkylcarbonyloxy group", one of the "C ₁ -C ₆ alkoxy group" or one phenoxy wherein the group is substituted "C ₂ -C _{1 0} alkyl group", preferably , the same or different 1 to 3 chlorine atoms, fluorine atom or bromine atom, one of the "C ₂ -C ₅ alkylcarbonyloxy group", one of the "C ₁ -C ₄ alkoxy group" Or the above “C ₂ -C ₈ substituted by one phenoxy group”
Alkylcarbonyl group ", and more preferably, one or two chlorine or fluorine atoms, which are the same or different,
One of said "C ₂ -C ₄ alkylcarbonyloxy group",
One "C ₁ -C ₃ alkoxy group" or the above "C ₂ -C ₆ alkylcarbonyl group" substituted by one phenoxy group, even more preferably one chlorine atom, methoxycarbonyl group, which is the the ethoxycarbonyl group, a methoxy group or an ethoxy group is substituted "C ₂ -C ₄ alkylcarbonyl group".

In the present invention, the “C ₄ -C ₇ cycloalkylcarbonyl group” is a group having 3 to 6 carbon atoms such as cyclopropylcarbonyl, cyclobutylcarbonyl, cyclopentylcarbonyl, cyclohexylcarbonyl and cycloheptylcarbonyl. Is a carbonyl group to which a cycloalkyl group is bonded, and is preferably a cyclopropylcarbonyl group.

In the substituent of the cycloalkylcarbonyl group for R ⁴ , “a phenyl group substituted by one C ₁ -C ₆ alkoxy group” includes, for example, methoxyphenyl, ethoxyphenyl, propoxyphenyl, isopropoxyphenyl, One such “C” such as butoxyphenyl, pentyloxyphenyl and hexyloxyphenyl
A ₁ -C ₆ phenyl group alkoxy group "is bonded, preferably a one phenyl group wherein the" C ₁ -C ₄ alkoxy group "bonded, more preferably, one of the" C ₁
A phenyl group to which a “-C ₃ alkoxy group” is bonded, and even more preferably an ethoxyphenyl group.

In R ⁴ of the present invention, “1 to 4 selected from the group consisting of a C ₁ -C ₆ alkyl group and a halogen atom”
Substituents, one or two C ₁ -C ₆ alkoxy groups, one or two cyano groups or one phenyl group (the phenyl group is substituted by one C ₁ -C ₆ alkoxy group . which may be) C ₄ -C ₇ cycloalkylcarbonyl group substituted by ", for example, methyl cyclopropanecarbonyl, dimethylcyclopropane carbonyl, trimethyl cyclopropanecarbonyl, tetramethyl cyclopropane carbonyl, methyl - dichloro cyclopropanecarbonyl, Cyanocyclopropanecarbonyl, phenylcyclopropanecarbonyl, (ethoxyphenyl) cyclopropanecarbonyl, (ethoxyphenyl) dichlorocyclopropanecarbonyl, methylcyclopentanecarbonyl,
The same or different ones selected from the group consisting of the aforementioned “C ₁ -C ₆ alkyl group” and the aforementioned “halogen atom”, such as methoxycyclopentanecarbonyl, methylcyclohexanecarbonyl and methoxycyclohexanecarbonyl;
1 to 2 substituents, 1 or 2 identical or different “C ₁ -C ₆ alkoxy groups”, 1 or 2 cyano groups, 1
Phenyl group or one said phenyl group substituted by one C ₁ -C ₆ alkoxy group, said “C ₄ -C ₇ cycloalkylcarbonyl group” substituted, "C ₁ -C ₄ alkyl group", a chlorine atom, the same or different 1 to 4 substituents selected from the group consisting of fluorine atom and bromine atom, the same or different 1 or 2 of the "C ₁ ~ C ₄ alkoxy group ", one or two cyano groups, one phenyl group or one of the" one C ₁ -C ₄
The aforementioned “C ₄ -C ₇ cycloalkylcarbonyl group” substituted by the “phenyl group substituted by an alkoxy group”,
More preferably, the “C ₁ -C ₃ alkyl group”, the same or different 1 to 4 substituents selected from the group consisting of a chlorine atom and a fluorine atom, and the same or different 1 or 2 A C ₁ -C ₃ alkoxy group, one cyano group, one phenyl group or one of the above “C substituted by _one “ C ₁ -C ₃ alkoxy group ”substituted phenyl group”
₄ -C ₇ cycloalkyl carbonyl group ", further preferably from is one of the" cyclopropylcarbonyl group C ₁ -C ₂ alkyl group "is substituted, particularly preferred,
It is a cyclopropylcarbonyl group substituted by one methyl group.

In the present invention, the "C ₃ -C ₇ alkenylcarbonyl group" includes, for example, acryloyl, 2-butenoyl, methylacryloyl, 3-butenoyl, 2-pentenoyl, 4-pentenoyl, 2-methyl-2-butenoyl, 3-methyl-2-butenoyl, 1-cyclohexenecarbonyl, 1-cyclopentenecarbonyl, 2-hexenoyl, 5-hexenoyl, 1-heptenoyl and 6
A carbonyl group to which a linear or branched alkenyl group having 2 to 6 carbon atoms such as heptenoyl is bonded, preferably a linear or branched alkenyl group having 2 to 5 carbon atoms. Is a carbonyl group (C ₃ -C ₆ alkenylcarbonyl group), more preferably a carbonyl group (C ₃ -C ₅₎ bonded to a linear or branched alkenyl group having 2 to 4 carbon atoms. An alkenylcarbonyl group), preferably a carbonyl group (C ₃ -C ₄ alkenylcarbonyl group) to which a linear or branched alkenyl group having 2 or 3 carbon atoms is bonded, more preferably, Allylcarbonyl group.

In the present invention, “C ₃ -C ₇ alkenylcarbonyl group substituted by 1 to 3 halogen atoms” includes, for example, chloroacryloyl, dichloroacryloyl, trichloroacryloyl, bromoacryloyl, fluoroacryloyl, dichlorobuteyl. Noyl, dichloropentenoyl and dichlorohexenoyl,
1 to 3 identical or different “halogen atoms” are the “C ₃ -C ₇ alkenylcarbonyl groups” substituted, preferably 1 to 3 identical or different chlorine atoms, fluorine atoms or The above “C ₃ -C ₆ substituted with a bromine atom”
An alkenylcarbonyl group ", more preferably a the same or different 1 or 2 chlorine atoms or a fluorine atom-substituted" C ₃ -C ₅ alkenyl group ", further preferably more, 1 or two C ₃ -C ₄ alkenylcarbonyl group which chlorine atom is substituted.

In the substituent of the benzoyl group for R ⁴ of the present invention, “C ₁ -C ₆ alkyl group substituted by 1 to 3 halogen atoms or 1 phenoxy group” includes, for example, monofluoromethyl, 1 to 3 identical or different said "halogen atoms" such as difluoromethyl, trifluoromethyl, chlorodifluoromethyl, trifluoroethyl, phenoxymethyl, phenoxyethyl, phenoxypropyl, phenoxybutyl, phenoxypentyl and phenoxyhexyl Or the above-mentioned “C ₁ -C ₆ alkyl group” substituted by one phenoxy group, preferably one or three same or different chlorine, fluorine or bromine atoms or one phenoxy group. substituted wherein a "C ₁ -C ₄ alkyl group", more preferably, the same or different To the three chlorine atoms or fluorine atoms or one phenoxy group is substituted is "C ₁ -C ₃ alkyl group", further preferably more, trifluoromethyl or phenoxymethyl group.

In the present invention, “C ₁ -C ₆ alkylsulfinyl group” includes, for example, methylsulfinyl, ethylsulfinyl, propylsulfinyl, isopropylsulfinyl, butylsulfinyl, tert-butylsulfinyl, pentylsulfinyl and hexylsulfinyl. It is a linear or branched alkylsulfinyl group having 1 to 6 carbon atoms, preferably having 1 carbon atom.
Straight-chain or branched-chain alkylsulfinyl group (C ₁ -C ₄ alkylsulfinyl group) having ₁ to ₄ carbon atoms, and more preferably a straight-chain or branched-chain alkylsulfinyl group having 1 to 3 carbon atoms (C ₁ -C ₄ ) ₁ -C ₃ alkylsulfinyl group)
And even more preferably a methylsulfinyl group.

The R of the present invention^FourIn the "Halogen atom and
And C₁~ C₆Alkyl group (1 to 3 alkyl groups
Substituted by one halogen atom or one phenoxy group
May be. 1) to 5 substitutions selected from the group consisting of
Group, 1 to 3 C₁~ C₆An alkoxy group, one C_Two~
C₇Alkylcarbonyloxy group, one C_Two~ C₇Al
Coxycarbonyl group, one C₁~ C₆Alkylthio group,
One C₁~ C₆Alkylsulfinyl group, one C₁~
C₆Alkylsulfonyl group, one phenoxy group, one
Substituted with one cyano group or one nitro group
An `` yl group '' is, for example, chlorobenzoyl, dichloroben
Zoyl, trichlorobenzoyl, methylbenzoyl, di
Methylbenzoyl, trimethylbenzoyl, methoxybe
Nzoyl, dimethoxybenzoyl, trimethoxybenzo
Yl, methyl-methoxybenzoyl, methyl-chlorobe
Nzoyl, trifluoromethylbenzoyl, phenoxy
Methylbenzoyl, acetoxybenzoyl, methoxyca
Rubonylbenzoyl, methylthiobenzoyl, methyls
Rufinylbenzoyl, methylsulfonylbenzoyl,
Phenoxybenzoyl, cyanobenzoyl and nitrove
The “halogen atom” and the “C₁
~ C₆Alkyl group "and the above" 1 to 3 halogen atoms "
C substituted by an atom or one phenoxy group₁~ C₆A
Or different ones selected from the group consisting of
From 5 to 5 substituents, identical or different from 1 to 3
"C₁~ C₆An alkoxy group "and one of the aforementioned" C_Two~ C₇Al
Alkylcarbonyloxy group ”and one of the aforementioned“ C_Two~ C₇Al
A oxycarbonyl group ”and one of the aforementioned“ C ₁~ C₆Alkyl
A thio group ”and one of the aforementioned“ C₁~ C₆Alkylsulfinyl
Group) and one of the aforementioned "C₁~ C₆Alkylsulfonyl group ",
One phenoxy group, one cyano group or one nitro group
Group is a substituted benzoyl group, preferably a chlorine atom
, A fluorine atom, a bromine atom,₁~ C_FourAlkyl
Group "and" 1 to 3 identical or different chlorine atoms,
By a nitrogen or bromine atom or a phenoxy group
Replaced C₁~ C_FourAlkyl group "
Same or different 1 to 3 substituents, same or different
One to three of the "C₁~ C_FourAlkoxy group ", 1
"C_Two~ C_FiveAlkylcarbonyloxy group ", 1
"C_Two~ C_FiveAn alkoxycarbonyl group "
The "C₁~ C_FourAlkylthio group ”, one of the above“ C₁~
C_FourAlkylsulfinyl group ", one of the aforementioned" C₁~ C_Four
Alkylsulfonyl group ", one phenoxy group, one
A benzoyl group substituted by a cyano group or one nitro group
And more preferably, a chlorine atom, a fluorine atom,
₁~ C_ThreeAlkyl group "and 1 to 3 identical or different
Chlorine atom or fluorine atom or one phenoxy group
C substituted by₁~ C_ThreeAlkyl group "
The same or different one or two substituents selected,
Represents one or two different “C”₁~ C_ThreeAlkoxy
Group) and one of the aforementioned "C_Two~ C_FourAlkylcarbonyloxy
Group) and one of the aforementioned "C_Two~ C_FourAlkoxycarbonyl
Group) and one of the aforementioned "C ₁~ C_ThreeAlkylthio group "
The "C₁~ C_ThreeAlkylsulfinyl group "
"C₁~ C_ThreeAlkylsulfonyl group ”, one phenoxy
Group substituted with one cyano group or one nitro group
A zoyl group, even more preferably a chlorobenzoi group.
, Fluorobenzoyl, difluorobenzoyl, methyl
Rubenzoyl, methoxybenzoyl, methylmethoxybe
Nzoyl, trifluoromethylbenzoyl, phenoxy
Methylbenzoyl, methoxybenzoyl, dimethoxybe
Nzoyl, trimethoxybenzoyl, ethoxybenzoi
, Propoxybenzoyl, acetoxybenzoyl,
Toxylcarbonylbenzoyl, methylthiobenzoyl,
Methylsulfinylbenzoyl, methylsulfonylben
Zoyl, phenoxybenzoyl, cyanobenzoyl or
It is a nitrobenzoyl group.

In the present invention, a “4- to 6-membered heterocyclic carbonyl group (the heterocyclic carbonyl group contains 1 to 4 oxygen atoms, sulfur atoms or nitrogen atoms, and may be bonded to a benzene ring. ) "Is, for example, chromancarbonyl, benzodioxolecarbonyl, pyridinecarbonyl, pyrimidinecarbonyl, pyrazinecarbonyl, pyridazinecarbonyl, pyrazolecarbonyl, thiazolecarbonyl, oxazolecarbonyl, isoxazolecarbonyl, thiadiazolecarbonyl, oxetanecarbonyl, N-morpholinecarbonyl , Such as, for example, tetrahydrofurancarbonyl and tetrahydropyrancarbonyl, which contain 1 to 4 oxygen, sulfur or nitrogen atoms in the ring and which may be condensed with a benzene ring; A carbonyl group to which a unsubstituted heterocyclic ring is bonded; preferably, the ring contains 1 to 3 oxygen atoms, sulfur atoms, or nitrogen atoms, and may be fused to a benzene ring; A carbonyl group to which a saturated or unsaturated heterocycle is bonded, more preferably a benzodioxolcarbonyl, pyridinecarbonyl, N-morpholinecarbonyl, oxetanecarbonyl, pyrazolecarbonyl, thiadiazolecarbonyl, pyrimidinecarbonyl or chromancarbonyl group. is there.

In the present invention, "1 to 3 C₁~ C₆
An alkyl group (the alkyl group is one to three halogens)
It may be replaced by an atom. ) 1 to 3 C₁~ C₆
An alkoxy group, one C₁~ C₆Alkylthio group or one
4- to 6-membered heterocyclic carb substituted by a halogen atom
A `` bonyl group '' is, for example, methylpyridinecarbonyl,
Tyl pyrimidine carbonyl, trifluoromethyl pyridi
Carbonyl, methyl-thiomethylpyrimidine carbonyl
Thiomethyl-trifluoromethylpyrimidine carb
Nil, dimethylpyrazolecarbonyl, methyl-trif
Fluoromethylpyrazolecarbonyl, methylthiazole
Carbonyl, methylthiadiazolecarbonyl, methyl
Oxetanecarbonyl and methyltetrahydrofuranca
1 to 3 of the same or different, such as rubonyl
"C₁~ C₆Alkyl group ", 1 to 3 identical or different
"C substituted by 1 to 3 halogen atoms₁~
C₆Alkyl group ", one or three of the same or different
"C₁~ C₆An alkoxy group "and one of the aforementioned" C₁~ C₆Al
A quinthio group ”or one of the aforementioned“ halogen atoms ”
The above “4- to 6-membered heterocyclic carbonyl group (the heterocyclic
A rubonyl group is one to four oxygen atoms, sulfur atoms or nitrogen atoms.
It may contain a hydrogen atom and may be bonded to a benzene ring. )"so
And preferably, one or two of the same or different
"C₁~ C_FourAlkyl group ", one or two identical or different
"1 to 3 chlorine, fluorine or bromine atoms
C replaced by₁~ C_FourAlkyl group ", the same or different
One or two of the above “C₁~ C_FourAn alkoxy group "
The "C₁~ C_FourAlkylthio group "or one chlorine atom,
A fluorine atom or a bromine atom bonded to the ring
Contains up to three oxygen, sulfur, or nitrogen atoms,
4- to 6-membered saturated or unsaturated
Carbonyl group to which a heterocyclic ring is bonded '', more preferably
Are the same or different one or two of the aforementioned “C₁~ C_ThreeAl
1 to 2 identical or different 1 to 3
Substituted by a chlorine or fluorine atom of ₁~ C_ThreeA
Alkyl group ", one or two of the same or different" C₁
~ C_ThreeAn alkoxy group "and one of the aforementioned" C₁~ C_ThreeAlkyl
A thio group "or one chlorine or fluorine atom
"1 to 3 oxygen atoms, sulfur atoms or nitrogen
Which contains a hydrogen atom and may be condensed with a benzene ring;
A carbonyl group to which a 6-membered saturated or unsaturated heterocyclic ring is bonded "
And even more preferably 1 or 2 identical or different
Methyl, ethyl, trifluoromethyl, methoxy
Or an ethoxy group, one methylthio, ethylthio, salt
Benzodioxo with elemental or fluorine atoms bonded
Carbonyl, pyridinecarbonyl, N-morpholine
Carbonyl, oxetanecarbonyl, pyrazolecar
Bonyl, thiadiazolecarbonyl, pyrimidinecarbo
Nyl or chromancarbonyl group.

In R ^{4 and} A of the present invention, “1 selected from the group consisting of a halogen atom and a C ₁ -C ₆ alkyl group”
Or a 5- or 6-membered heterocyclic group substituted by two substituents "is, for example, chloropyrazolyl, methylpyrazolyl, dimethylpyrazolyl, chloro-methylpyrazolyl,
Chloropyridyl, fluoropyridyl, methylpyridyl,
Chloropyrimidinyl, methylpyrimidinyl, methyltetrahydrofuranyl, methyltetrahydropyranyl, methyldioxolanyl, methylthienyl, chlorothienyl,
Such as methylfuranyl and methylisoxazolyl,
The “halogen atom” and the “C ₁ -C ₆ alkyl group”
Wherein the same or different 1 or 2 substituents selected from the group consisting of the above “5- or 6-membered heterocyclic group (the heterocyclic group has 1 to 4 oxygen atoms, sulfur atoms or nitrogen atoms, And the same or different one or two substituents selected from the group consisting of a chlorine atom, a fluorine atom, a bromine atom and the above-mentioned “C ₁ -C ₄ alkyl group” are preferably substituted. A saturated or unsaturated 5 or 6 ring containing 1 to 3 oxygen, sulfur or nitrogen atoms
Membered heterocyclic group '', and more preferably, substituted by one or two identical or different substituents selected from the group consisting of a chlorine atom, a fluorine atom and the above-mentioned “C ₁ -C ₃ alkyl group”. A saturated or unsaturated 5- or 6-membered heterocyclic group containing one or two oxygen atoms or nitrogen atoms in the ring ", and even more preferably one chlorine atom, fluorine atom, methyl group or ethyl The group is a substituted pyridyl group, thienyl group or tetrahydrofuranyl group.

R of the present invention^FourIn the above, "1 to 3 c
A logen atom, one C₁~ C₆An alkoxy group, one C₁
~ C₆Alkylthio group, one phenyl group (the phenyl
Group is a halogen atom and C₁~ C₆Consists of an alkyl group
Substituted with 1 to 5 substituents selected from the group.
No. ) Or one 5- or 6-membered heterocyclic group (the heterocyclic
The group has 1 to 4 oxygen, sulfur or nitrogen atoms.
Containing a halogen atom and C₁~ C₆Consists of an alkyl group
Substituted by one or two substituents selected from the group
No. C) substituted by_Two~ C₈Alkoxycarbonyl
"Group" is, for example, 2-methoxyethoxycarbonyl, 2
-Isopropoxyethoxycarbonyl, 2-phenoxy
Ethoxycarbonyl, 2-methylthioethoxycarboni
, 2-tetrahydrofuranylmethoxycarbonyl, 3
-Chloro-2,2-dimethylpropoxycarbonyl,
2,2,2-trichloroethoxycarbonyl, 2,2
The same or similar, such as 2-trifluoroethoxycarbonyl
Are 1 to 3 different “halogen atoms”, 1
The "C₁~ C₆An alkoxy group "and one of the aforementioned" C₁~ C₆
Alkylthio group ", one phenyl group, and one
Logen atom and C₁~ C₆Selected from the group consisting of alkyl groups
Substituted with 1 to 5 substituents
Group) and one of the aforementioned “5- or 6-membered heterocyclic groups (the heterocyclic
The ring group has 1 to 4 oxygen atoms, sulfur atoms or nitrogen
Contains atoms. )) Or one of the aforementioned “halogen atoms and
And C₁~ C₆1 or 2 selected from the group consisting of alkyl groups
5- or 6-membered heterocyclic group substituted by two substituents "
"C substituted by_Two~ C₈Alkoxycarbonyl
Group), preferably 1 to 3 identical or different
A chlorine atom, a fluorine atom or a bromine atom,
"C₁~ C_FourAn alkoxy group "and one of the aforementioned" C₁~ C_FourAl
A thiothio group), one phenyl group, and one
Atom, fluorine atom, bromine atom and C₁~ C_FourFrom an alkyl group
Substituted with one to three substituents selected from the group consisting of
Phenyl group ", one" ring has 1 to 3 oxygen atoms,
Saturated or unsaturated 5- or 5-sulfur-containing or nitrogen-containing
Or a 6-membered heterocyclic group "or one" chlorine atom, fluorine atom
Child, bromine atom and C₁~ C_FourSelect from the group consisting of alkyl groups
Substituted by one or two identical or different substituents
One to three oxygen, sulfur or nitrogen atoms
Saturated or unsaturated 5- or 6-membered heterocyclic ring
"C" substituted by "group"_Two~ C₈Alkoxycarbo
And more preferably one or the same or different
Up to three chlorine atoms or fluorine atoms, and one
₁~ C_ThreeAn alkoxy group "and one of the aforementioned" C₁~ C_ThreeAlkyl
A thio group ", one phenyl group or one" 1 or 2
Saturated or unsaturated containing oxygen or nitrogen atoms
The above-mentioned “C substituted by a 5- or 6-membered heterocyclic group” _Two
~ C₈Alkoxycarbonyl group ", even more preferred
Are the same one to three chlorine atoms or fluorine atoms
Child, one of the "C₁~ C_TwoAlkoxy group ", one of the above
"C₁~ C_TwoAlkylthio group ", one phenyl group or one
Pyridyl, thienyl or tetrahydrofura
The above-mentioned “C substituted by a nyl group_Two~ C_ThreeAlkoxycal
Bonyl group ".

In the present invention, the “C ₄ -C ₇ cycloalkoxycarbonyl group” is a group having 3 to 6 carbon atoms such as cyclopropoxycarbonyl, cyclobutoxycarbonyl, cyclopentoxycarbonyl and cyclohexyloxycarbonyl. A carbonyl group to which a certain cycloalkoxy group is bonded, preferably a carbonyl group to which a cycloalkoxy group having 4 to 6 carbon atoms is bonded (C ₅ -C ₇ cycloalkoxycarbonyl group), more preferably Is a carbonyl group (C ₆ -C ₇ cycloalkoxycarbonyl group) to which a cycloalkoxy group having 5 or 6 carbon atoms is bonded, and even more preferably a cyclopentoxycarbonyl group.

In the present invention, “C ₃ -C ₇ alkenyloxycarbonyl” includes, for example, vinyloxycarbonyl, 2-propenyloxycarbonyl, 1-methyl-2
-Propenyloxycarbonyl, 2-methyl-2-propenyloxycarbonyl, 2-butenyloxycarbonyl, 3-methyl-2-butenyloxycarbonyl, 1-
A linear or branched alkenyloxy group having 2 to 6 carbon atoms such as methyl-2-butenyloxycarbonyl, 3-butenyloxycarbonyl, 2-pentenyloxycarbonyl and 5-hexenyloxycarbonyl is bonded. A carbonyl group (C ₄ -C ₇ alkenyloxycarbonyl group) to which a linear or branched alkenyloxy group having 3 to 6 carbon atoms is bonded, more preferably A carbonyl group (C ₄ -C ₆ alkenyloxycarbonyl group) to which a linear or branched alkenyloxy group having 3 to 5 carbon atoms is bonded, and still more preferably 3 or 4 carbon atoms. a is a straight-chain or branched-chain alkenyloxy group bonded to a carbonyl group (C ₄ -C ₅ alkenyloxycarbonyl group), particularly preferably, Seo is a propoxycarbonyl group or a butoxycarbonyl group.

In the present invention, “C ₃ -C ₇ alkynyloxycarbonyl group” includes, for example, propargyloxycarbonyl, 1,1-dimethylpropargyloxycarbonyl, 3-butynyloxycarbonyl, 4-pentynyloxycarbonyl and A carbonyl group to which a linear or branched alkynyloxy group having 2 to 6 carbon atoms such as -hexynyloxycarbonyl is bonded, preferably a linear or branched alkynyloxy group having 2 to 5 carbon atoms; A carbonyl group to which a branched-chain alkynyloxy group is bonded (C ₃ -C ₆ alkynyloxycarbonyl group), more preferably a carbonyl group to which a linear or branched alkynyloxy group having 3 to 5 carbon atoms is bonded. a group (C ₄ -C ₆ alkynyloxy carbonyl group), further preferably more, is methylbutynyl group

In the present invention, “(C ₁ -C ₆ alkylthio) carbonyl” includes, for example, (methylthio) carbonyl, (ethylthio) carbonyl, (propylthio) carbonyl, (isopropylthio) carbonyl, (butylthio) carbonyl, Isobutylthio) carbonyl,
(Sec-butylthio) carbonyl, (tert-butylthio)
Carbonyl, (pentylthio) carbonyl, (2-methylbutylthio) carbonyl, (1-methylpentylthio) carbonyl, (neopentylthio) carbonyl,
Straight chain having 1 to 6 carbon atoms, such as (hexylthio) carbonyl, (1-methylhexylthio) carbonyl, (3,3-dimethylbutylthio) carbonyl and (2,2-dimethylbutylthio) carbonyl; A carbonyl group to which a branched alkylthio group is bonded, preferably
A carbonyl group to which a linear or branched alkylthio group having 1 to 4 carbon atoms is bonded, more preferably a carbonyl group to which a linear or branched alkylthio group having 1 to 3 carbon atoms is bonded. And a carbonyl group to which an alkylthio group having 1 or 2 carbon atoms is bonded, and more preferably a (methylthio) carbonyl group.

In the present invention, "halogen atom and C ₁
~C substituted by 1 to 5 substituents selected from the group consisting of _alkyl groups (phenylthio) carbonyl group ", for example, (chlorophenylthio) carbonyl,
(Dichlorophenylthio) carbonyl, (trichlorophenylthio) carbonyl, (fluorophenylthio) carbonyl, (difluorophenylthio) carbonyl,
(Trifluorophenylthio) carbonyl, (pentafluorophenylthio) carbonyl, (bromophenylthio) carbonyl, (iodophenylthio) carbonyl,
(Chlorofluorophenylthio) carbonyl, (methylphenylthio) carbonyl, (ethylphenylthio) carbonyl, (propylphenylthio) carbonyl, (isopropylphenylthio) carbonyl, (butylphenylthio) carbonyl, (tert-butylphenylthio) carbonyl, such as (pentylphenyl thio) carbonyl and (hexyl phenyl thio) carbonyl, the "halogen atom" and the from the group consisting of "C ₁ -C ₆ alkyl group" same or different 1 to 5 substituents selected A carbonyl group to which a phenylthio group substituted by a substituent is bonded, and preferably the same or different ₁ to ₄ groups selected from the group consisting of a chlorine atom, a fluorine atom, a bromine atom and the above-mentioned “C ₁ -C ₄ alkyl group”; (Phenylthio) carbonyl group substituted by three substituents There, more preferably, is chlorine atom, the same or different 1 or 2 substituents selected from a fluorine atom and the group consisting of the "C ₁ -C ₂ alkyl group" is substituted (phenylthio) carbonyl group And more preferably a (phenylthio) carbonyl group substituted with one chlorine atom, fluorine atom or methyl group.

In the present invention, “(C ₁ -C ₆ alkoxy) thiocarbonyl group” includes, for example, (methoxy) thiocarbonyl, (ethoxy) thiocarbonyl, (propoxy) thiocarbonyl, (isopropoxy) thiocarbonyl, (Butoxy) thiocarbonyl, (isobutoxy) thiocarbonyl, (sec-butoxy) thiocarbonyl, (te
(rt-butoxy) thiocarbonyl, (pentoxy) thiocarbonyl, (isopentoxy) thiocarbonyl, (2-
Methylbutoxy) thiocarbonyl, (neopentoxy)
Thiocarbonyl, (1-ethylpropoxy) thiocarbonyl, (hexyloxy) thiocarbonyl, (1-methylpentoxy) thiocarbonyl, (3,3-dimethylbutoxy) thiocarbonyl, (1,1-dimethylbutoxy) thiocarbonyl A thiocarbonyl group to which a linear or branched alkoxy group having 1 to 6 carbon atoms such as (1,2-dimethylbutoxy) thiocarbonyl and (2-ethylbutoxy) thiocarbonyl is bonded; Is a thiocarbonyl group {(C ₁ -C ₄ alkoxy) thiocarbonyl group} to which a linear or branched alkoxy group having ₁ to ₄ carbon atoms is bonded, and more preferably 1 carbon atom. And a thiocarbonyl group {(C ₁ -C ₃ alkoxy) thiocarbonyl group} to which three or three linear or branched alkoxy groups are bonded. And even more preferably a (methoxy) thiocarbonyl group or a (ethoxy) thiocarbonyl group.

In the present invention, “halogen atom and C ₁
“(Phenoxy) thiocarbonyl group substituted by 1 to 5 substituents selected from the group consisting of —C ₆ alkyl group” includes, for example, (chlorophenoxy) thiocarbonyl, (dichlorophenoxy) thiocarbonyl, (trichlorophenoxy) ) Thiocarbonyl, (fluorophenoxy) thiocarbonyl, (difluorophenoxy) thiocarbonyl, (trifluorophenoxy) thiocarbonyl, (pentafluorophenoxy) thiocarbonyl,
(Bromophenoxy) thiocarbonyl, (iodophenoxy) thiocarbonyl, (chlorofluorophenoxy)
Thiocarbonyl, (methylphenoxy) thiocarbonyl, (ethylphenoxy) thiocarbonyl, (propylphenoxy) thiocarbonyl, (isopropylphenoxy) thiocarbonyl, (butylphenoxy) thiocarbonyl, (tert-butylphenoxy) thiocarbonyl,
1 to 5 identical or different substituents selected from the group consisting of the aforementioned “halogen atom” and the aforementioned “C ₁ -C ₆ alkyl group”, such as (pentylphenoxy) thiocarbonyl and (hexylphenoxy) thiocarbonyl Is a thiocarbonyl group to which a substituted phenoxy group is bonded, preferably a chlorine atom, a fluorine atom, a bromine atom and the aforementioned “C
₁ -C is the ₄ same or different 1 to 3 substituents selected from the group consisting of alkyl group "is substituted (phenoxy) thiocarbonyl group, more preferably a chlorine atom, a fluorine atom, and the" C ₁ -C is ₃ same or different 1 to 3 substituents selected from the group consisting of alkyl group "is substituted (phenoxy) thiocarbonyl group, further preferably more, a chlorine atom, a fluorine atom, a bromine atom And the "C
_1- C ₂ alkyl groups ”are the same or different 1 or 2 substituents selected from the group consisting of a substituted (phenoxy) thiocarbonyl group, particularly preferably a (chlorophenoxy) thiocarbonyl group; A fluorophenoxy) thiocarbonyl group or a (methylphenoxy) thiocarbonyl group.

In the present invention, "C_Two~ C₇Alkyl dithi
“Ocarbonyl group” is, for example, methyldithiocarboni
, Ethyldithiocarbonyl, propyldithiocarboni
, Isopropyldithiocarbonyl, butyldithiocar
Bonyl, isobutyldithiocarbonyl, sec-butyldithi
Ocarbonyl, tert-butyldithiocarbonyl, pliers
Rudithiocarbonyl, 2-methylbutyldithiocarboni
, 1-methylpentyldithiocarbonyl, neopentene
Rudithiocarbonyl, hexyldithiocarbonyl, 1-
Methylhexyldithiocarbonyl, 3,3-dimethylbut
Tyldithiocarbonyl and 2,2-dimethylbutyldithi
A straight chain having 1 to 6 carbon atoms, such as ocarbonyl or
A thiocarbonyl group to which a branched alkylthio group is bonded
And preferably a straight-chain or branched-chain alkyl group having 1 to 5 carbon atoms.
Thiocarbonyl group (C_Two~ C₆A
Lucidylthiocarbonyl group), and more preferably, charcoal.
A linear or branched alkylthio group having 1 to 4
Combined thiocarbonyl group (C _Two~ C_FiveAlkyl dithiocal
Bonyl group), and even more preferably, the number of carbon atoms is 1 to
Thioca having three linear or branched alkylthio groups bonded
Rubonyl group (C_Two~ C_FourAlkyldithiocarbonyl group)
And particularly preferably a methyldithiocarbonyl group or
It is a tildithiocarbonyl group.

In the present invention, “halogen atom and C ₁
-C ₆ phenyl dithio group which is substituted by 1 to 5 substituents selected from the group consisting of alkyl group "
Is, for example, chlorophenyldithiocarbonyl, dichlorophenyldithiocarbonyl, trichlorophenyldithiocarbonyl, fluorophenyldithiocarbonyl, difluorophenyldithiocarbonyl, trifluorophenyldithiocarbonyl, pentafluorophenyldithiocarbonyl, bromophenyldithiocarbonyl, iodophenyldithiocarbonyl, chloro Such as fluorophenyldithiocarbonyl, methylphenyldithiocarbonyl, ethylphenyldithiocarbonyl, propylphenyldithiocarbonyl, isopropylphenyldithiocarbonyl, butylphenyldithiocarbonyl, tert-butylphenyldithiocarbonyl, pentylphenyldithiocarbonyl, hexylphenyldithiocarbonyl,
The “halogen atom” and the “C ₁ -C ₆ alkyl group”
And a thiocarbonyl group to which a phenylthio group substituted by the same or different 1 to 5 substituents selected from the group consisting of: a chlorine atom, a fluorine atom, a bromine atom, and the above-mentioned “C ₁ -C A thiocarbonyl group to which a phenylthio group substituted by 1 to 3 identical or different substituents selected from the group consisting of ₄ alkyl groups is bonded, and more preferably a chlorine atom, a fluorine atom and the above-mentioned “C ₁ ~ C ₂
Alkyl group "is a phenyldithiocarbonyl group substituted with one or two same or different substituents selected from the group consisting of chlorophenyldithiocarbonyl group, fluorophenyldithiocarbonyl group and methylphenyldithiocarbonyl group. Group.

In the present invention, “halogen atom and C ₁
A phenoxy group substituted by 1 to 5 substituents selected from the group consisting of ＣC ₆ alkyl groups ”includes, for example, chlorophenoxy, dichlorophenoxy, trichlorophenoxy, fluorophenoxy, difluorophenoxy,
Trifluorophenoxy, pentafluorophenoxy,
Bromophenoxy, iodophenoxy, chloro fluorophenoxy, methylphenoxy, ethylphenoxy, propylphenoxy, isopropylphenoxy, butylphenoxy, tert- butyl phenoxy, pentylphenoxy, such as hexylphenoxy, the "halogen atom" and the "C ₁ ~ A phenoxy group substituted with 1 to 5 identical or different substituents selected from the group consisting of “C ₆ alkyl group”, preferably a chlorine atom, a fluorine atom, a bromine atom and the above “C ₁ -C ₄ Alkyl group "is a phenoxy group substituted with 1 to 3 identical or different substituents selected from the group consisting of chlorine atoms, fluorine atoms and the above-mentioned" C ₁ -C ₃ alkyl group ". Phenoxy substituted by one or two same or different substituents selected from the group consisting of , Still preferably more, chlorophenoxy group, a fluorophenoxy group or methylphenoxy radical.

In R ⁴ of the present invention, “1 phenyl group (1 to 5 phenyl groups selected from the group consisting of a halogen atom, a C ₁ -C ₆ alkyl group and a C ₁ -C ₆ alkoxy group) May be substituted by a substituent of the formula :), C _1-
C ₆ alkoxy group, (C ₁ -C ₆ alkoxy) C ₁ -C ₆ alkoxy group, C ₁ -C ₆ alkylthio group, cyano group, phenoxy group (the phenoxy group is a halogen atom and C ₁
It may be substituted by 1 to 5 substituents selected from the group consisting of -C ₆ alkyl group. ) Or C ₂ -C ₇ alkoxycarbonyl C ₁ -C ₆ alkyl group substituted with a group "
Is, for example, benzyl, 2-phenylethyl, 1-phenylethyl, methoxymethyl, ethoxymethyl, propoxymethyl, butoxymethyl, pentyloxymethyl,
One phenyl group, such as hexyloxymethyl, methoxyethyl, ethoxyethyl, methoxypropyl, 4-cyanobutyl, phenoxymethyl, 2-phenoxyethyl, methoxycarbonylmethyl, ethoxycarbonylmethyl, ₁ selected from the group consisting of a C ₁ -C ₆ alkyl group and a C ₁ -C ₆ alkoxy group
A phenyl group substituted by 5 to 5 substituents, one of the above-mentioned “C ₁ -C ₆ alkoxy groups”, and one of the above-mentioned “(C ₁
-C ₆ alkoxy) C ₁ -C ₆ alkoxy group ”, one of the above“ C ₁ -C ₆ alkylthio groups ”, one cyano group, one phenoxy group, one“ halogen atom and C ₁ -C ₆ -alkoxy group ”. A phenoxy group substituted by 1 to 5 substituents selected from the group consisting of C ₆ alkyl groups ”or one of the above“ C _2-
The aforementioned “C ₁ -C ₇ ” substituted by “C ₇ alkoxycarbonyl group”
₆ alkyl group ", preferably one phenyl group,
One of the above “chlorine atom, fluorine atom, bromine atom, C _1-
A phenyl group substituted by 1 to 3 substituents selected from the group consisting of a C ₄ alkyl group and a C ₁ -C ₄ alkoxy group, one “C ₁ -C ₄ alkoxy group”, The above-mentioned “(C ₁ -C ₄ alkoxy) C ₁ -C ₄ alkoxy group”, one “C ₁ -C ₄ alkylthio group”, one cyano group, one phenoxy group, one “chlorine” A phenoxy group substituted by one to three substituents selected from the group consisting of an atom, a fluorine atom, a bromine atom and a C ₁ -C ₄ alkyl group ”or one of the above“ C ₂ -C ₅ alkoxycarbonyl groups ” Is a substituted C ₁ -C ₃ alkyl group, more preferably one phenyl group, and one C
₁ -C ₃ alkoxy group ", one of the" (C ₁ -C ₃ alkoxy) C ₁ -C ₃ alkoxy group ", one of the" C ₁ -C ₃
Alkylthio group ", one cyano group, one phenoxy group or one of the" C ₂ -C ₄ alkoxycarbonyl group "
Is a substituted “C ₁ -C ₃ alkyl group”, and even more preferably a methoxymethyl group.

In the present invention, "two alkyl groups are
5 or 6 together with the nitrogen atom to which they are attached
A di (C ₁ -C ₆ alkyl) carbamoyl group which forms a membered heterocyclic ring (the heterocyclic ring may contain one oxygen atom or one nitrogen atom in addition to one nitrogen atom) is, for example, , N
-Morpholinecarbonyl, N-piperidinecarbonyl,
As in N-piperazinecarbonyl, N-pyrrolidinecarbonyl and N-pyrazolinecarbonyl, a nitrogen atom and its adjacent carbon atoms form a saturated or unsaturated 5- or 6-membered heterocyclic ring, and one more in addition to the nitrogen atom. Is a carbonyl group bonded at the nitrogen atom, and is preferably N-morpholinecarbonyl or N-piperidinecarbonyl.

In the present invention, “di (C ₁ -C ₆ alkyl) thiocarbamoyl group” includes, for example, dimethylthiocarbamoyl, ethylmethylthiocarbamoyl, diethylthiocarbamoyl, dipropylthiocarbamoyl, diisopropylthiocarbamoyl, dibutylthiocarbamoyl, A thiocarbamoyl group in which two identical or different straight-chain or branched alkyl groups having 1 to 6 carbon atoms are bonded to a nitrogen atom, such as dipentylthiocarbamoyl and dihexylthiocarbamoyl, are preferably the same or different. A thiocarbamoyl group in which two different linear or branched alkyl groups having 1 to 4 carbon atoms are bonded to a nitrogen atom, more preferably 2 to 3 identical or different carbon atoms. Thioca having a linear or branched alkyl group bonded to a nitrogen atom A Bamoiru group, still more preferably a thiocarbamoyl group which alkyl group two identical carbon number of 1 or 2 is bonded to the nitrogen atom.

In the present invention, “two alkyl groups are
5 or 6 together with the nitrogen atom to which they are attached
A di (C ₁ -C ₆ alkyl) thiocarbamoyl group forming a membered heterocyclic ring (the heterocyclic ring may contain one oxygen atom or one nitrogen atom in addition to one nitrogen atom) is For example, as in N-morpholine thiocarbonyl, N-piperidine thiocarbonyl, N-piperazine thiocarbonyl, N-pyrrolidine thiocarbonyl and N-pyrazolin thiocarbonyl, the nitrogen atom and its adjacent carbon atoms are saturated or unsaturated. Alternatively, a heterocyclic ring which forms a 6-membered heterocyclic ring and further contains one oxygen atom or nitrogen atom in addition to the nitrogen atom is a thiocarbonyl group bonded at the nitrogen atom, and is preferably N-morpholinethione. Carbonyl or N-
Piperidinethiocarbonyl.

In the present invention, “di (C ₁ -C ₆ alkoxy) thiophosphoryl group” refers to, for example, di (methoxy)
Thiophosphoryl, di (ethoxy) thiophosphoryl, di (propoxy) thiophosphoryl, di (isopropoxy)
Thiophosphoryl, di (butoxy) thiophosphoryl, di (isobutoxy) thiophosphoryl, di (sec-butoxy)
Thiophosphoryl, di (tert-butoxy) thiophosphoryl, di (pentoxy) thiophosphoryl, di (isopentoxy) thiophosphoryl, di (2-methylbutoxy) thiophosphoryl, di (neopentoxy) thiophosphoryl, di (1-ethylpropoxy) Thiophosphoryl, di (hexyloxy) thiophosphoryl, di (1-methylpentoxy) thiophosphoryl, di (3,3-dimethylbutoxy)
The same or different 2 such as thiophosphoryl, di (1,1-dimethylbutoxy) thiophosphoryl, di (1,2-dimethylbutoxy) thiophosphoryl, di (2-ethylbutoxy) thiophosphoryl, methoxyethoxythiophosphoryl; Thiophosphoryl groups to which the above “C ₁ -C ₆ alkoxy groups” are bonded, preferably two or more of the same or different
Thiophosphoryl groups to which two “C ₁ -C ₄ alkoxy groups” are bonded, more preferably a thiophosphoryl group to which two identical or different “C ₁ -C ₃ alkoxy groups” are bonded. And even more preferably a thiophosphoryl group to which two identical “C ₁ -C ₂ alkoxy groups” are bonded.

In A of the present invention, “C ₁ -C ₆ alkyl group substituted by 1 to 13 halogen atoms” includes, for example, monofluoromethyl, monochloromethyl,
The same or different, such as difluoromethyl, dichloromethyl, trifluoromethyl, monofluoroethyl, monofluorohexyl, trifluoroethyl, pentafluoroethyl, heptafluoropropyl, nonafluorobutyl, undecafluoropentyl and tridecafluorohexyl And the above-mentioned "C ₁ -C ₆ alkyl group" substituted with 1 to 13 of the above-mentioned "halogen atoms", preferably 1 to 5 same or different chlorine, fluorine or bromine atoms are substituted. is said that the "C ₁ -C ₄ alkyl group", more preferably a the same or different 1 to 3 chlorine atoms or fluorine atom-substituted "C ₁ -C ₃ alkyl group", further by preferably a said that three fluorine atoms were substituted "C ₁ -C ₂ alkyl group", particularly preferred, triflic Is a Romechiru group.

In the present invention, R¹Is preferably hydrogen
Atom, C₁~ C_FourAlkyl group << the alkyl group is
C_Three~ C₇A cycloalkyl group, one phenyl group (the
Phenyl is 1 to 3 chlorine atoms, fluorine atoms, bromine
Atom or C₁~ C_FourMay be substituted by an alkyl group
No. ) One or two C₁~ C_FourAlkoxy group (the
Coxy groups have 1 to 5 chlorine atoms, fluorine atoms or odors.
It may be substituted by an elementary atom. ) One C_Three~ C_FiveAl
Kenyloxy group, one (C₁~ C_FourAlkoxy) C₁~
C_FourAn alkoxy group, one benzyloxy group, one C₁
~ C_FourAlkylthio group, 1 to 3 chlorine atoms, fluorine
Atom or bromine atom, one cyano group, one di (C
₁~ C_FourAlkyl) amino group or one 5- or 6-membered compound
A heterocyclic group ｛the heterocyclic group has 1 to 3 oxygen atoms,
Containing one or two chlorine atoms,
Nitrogen atom, bromine atom or C₁~ C_FourAlkyl group
The kill group is one to three chlorine atoms, fluorine atoms or bromine.
It may be replaced by an atom. )
No. May be replaced by｝. 》, C_Three~ C₇Cycloal
Kill group, C_Three~ C_FiveAn alkenyl group (the alkenyl group is
By 1 to 3 chlorine, fluorine or bromine atoms
It may be replaced. ), C_Three~ C_FiveAlkynyl group, phenyl
Group (the phenyl group is a chlorine atom, a fluorine atom, a bromine atom
Child and C₁~ C_Four1 selected from the group consisting of alkyl groups
It may be substituted by up to three substituents. ) 5 or
6-membered heterocyclic group—the heterocyclic group has 1 to 3 oxygen atoms
Containing a carbon atom, a sulfur atom or a nitrogen atom,₁~ C_FourA
Alkyl group (the alkyl group has 1 to 3 chlorine atoms,
It may be substituted by a fluorine atom or a bromine atom. By)
May be replaced. ｝, C_Two~ C₈Alkylcarbonyl group
(The alkylcarbonyl group is one to three chlorine atoms.
Atom, fluorine atom or bromine atom, one C₁~ C_FourAl
Substituted by a oxy group or one phenoxy group.
No. ), A benzoyl group (the benzoyl group is a chlorine atom
Atom, fluorine atom, bromine atom and C₁~ C_FourFrom an alkyl group
Substituted with one to three substituents selected from the group consisting of
May be. ), C_Two~ C_FiveAn alkoxycarbonyl group, di (C
₁~ C_FourAlkyl) carbamoyl group, C₁~ C_FourAlkyls
A ruphonyl group or a phenylsulfonyl group (the phenyls
A ruphonyl group is a chlorine atom, a fluorine atom, a bromine atom,
₁~ C_Four1 to 3 members selected from the group consisting of alkyl groups
It may be substituted by a substituent. ) And more preferably
Is a hydrogen atom, C₁~ C_ThreeAlkyl group ｛The alkyl group
Is one C _Three~ C₆Cycloalkyl group, one phenyl
Group, one or two C₁~ C_ThreeAlkoxy group (the alkoxy
The group is substituted by 1 to 3 chlorine atoms or fluorine atoms.
May be replaced. ), One (C₁~ C_ThreeAlkoxy) C₁
~ C_ThreeAn alkoxy group, one benzyloxy group, one
C₁~ C_ThreeAn alkylthio group, one to three chlorine atoms or
Is a fluorine atom, one cyano group or one 5 or 6
Membered heterocyclic group (the heterocyclic group has one or two oxygen atoms or
Contains a nitrogen atom. ). ｝,
C_Three~ C₆Cycloalkyl group, C_Three~ C_FourAlkenyl group (this
The alkenyl group has one or two chlorine atoms or fluorine atoms.
May be replaced by a child. ), C_Three~ C_FourAlkynyl group,
Phenyl group, 5- or 6-membered heterocyclic group (the heterocyclic group
Contains one or two oxygen or nitrogen atoms
You. ), C_Two~ C₆Alkylcarbonyl group, benzoyl
Group, C_Two~ C_FourAn alkoxycarbonyl group, di (C₁~ C_ThreeA
Alkyl) carbamoyl group, C₁~ C_ThreeAlkylsulfonyl
Or a phenylsulfonyl group, even more preferably
Is C₁~ C_TwoAlkyl group—the alkyl group has one C
₁~ C_TwoAn alkoxy group, one (C₁~ C_TwoAlkoxy) C
₁~ C_TwoAn alkoxy group or one C₁~ C_TwoAlkylthio group
May be replaced by ｝, Particularly preferably C₁
~ C_TwoAn alkyl group (the alkyl group has one C₁~ C_Two
It may be substituted by an alkoxy group. ).

In the present invention, R^TwoAnd R^ThreeIs preferably
Are the same or different and C₁~ C_FourAlkyl group ｛Al
The kill group is one C_Three~ C₇A cycloalkyl group, one
Phenyl group (the phenyl group is a chlorine atom, a fluorine atom,
Bromine atom, C₁~ C_FourAlkyl group and C₁~ C_FourAlkoxy
With one to three substituents selected from the group consisting of
May be replaced. ) One or two C₁~ C_FourAlkoxy
Group, one (C₁~ C_FourAlkoxy) C₁~ C_FourAlkoxy
Group, 1 to 5 chlorine atoms, fluorine atoms or bromine atoms
Or one 5- or 6-membered heterocyclic group (the heterocyclic group
Contains one to three oxygen, sulfur or nitrogen atoms.
Have. ). ｝, C_Three~ C₇Cyclo
Alkyl group, C_Three~ C_FiveAlkenyl group (the alkenyl group
Represents 1 to 3 chlorine, fluorine or bromine atoms
More may be substituted. ), C_Three~ C_FiveAlkynyl group, Fe
Nil group (the phenyl group is a chlorine atom, a fluorine atom,
Elementary atom, C₁~ C_FourAlkyl group and C₁~ C_FourAlkoxy group
Substituted with 1 to 3 substituents selected from the group consisting of
May be. ) Or a 5- or 6-membered heterocyclic group
The ring group has 1 to 3 oxygen, sulfur or nitrogen atoms
Containing a chlorine atom, a fluorine atom, a bromine atom and C₁~
C_FourAn alkyl group (where the alkyl group is one to three chlorine atoms)
Atom, fluorine atom or bromine atom
No. 1) or 2 substituents selected from the group consisting of
May be replaced. Represents｝, or R^TwoAnd R^ThreeIs
Together with the carbon atom to which they are attached, 4-7
Member, cycloalkane, cycloalkene or cyclo
Alkanediene ring—the ring is one to three C₁~ C_FourA
Alkyl group, one C₁~ C_FourAn alkoxy group, one (C₁
~ C_FourAlkoxy) C₁~ C_FourAn alkoxy group, one di
(C₁~ C_FourAlkyl) amino group, one methylenedioxy
1 group, 1 ethylenedioxy group, 1 trimethylene
A dioxy group or one N- (C₁~ C_FourAlkoxy) imi
A ring at any position.
Atom, sulfur atom or formula NR^6aA group represented by the formula:
^6aIs C ₁~ C_FourRepresents an alkyl group. Interrupted by
May be. ｝, More preferably the same or different
And C₁~ C_ThreeAlkyl group—the alkyl group has one C
_Three~ C₆A cycloalkyl group, one phenyl group (the
Nyl group is a chlorine atom, a fluorine atom, C₁~ C_ThreeAlkyl group
And C₁~ C_ThreeOne or more selected from the group consisting of alkoxy groups
May be substituted by two substituents. ) 1 or 2
C₁~ C_ThreeAn alkoxy group, one (C₁~ C_ThreeAlkoki
C) C₁~ C_ThreeAlkoxy groups, 1 to 3 chlorine atoms
Or a fluorine atom or one 5- or 6-membered heterocyclic group (such as
The heterocyclic group contains one or two oxygen or nitrogen atoms.
Have. ). ｝, C_Three~ C₆Cyclo
Alkyl group, C_Three~ C_FourAlkenyl group, C_Three~ C_FourAlkini
A phenyl group (the phenyl group comprises one or two C
₁~ C_ThreeIt may be substituted by an alkoxy group. ) Or 5 young
Or a 6-membered heterocyclic group (the heterocyclic group is one or two acids
Contains elemental or nitrogen atoms. ) Or R^Two
And R^ThreeTogether with the carbon atom to which they are attached
A 4- to 6-membered cycloalkane, cycloalkene
Or a cycloalkanediene ring, wherein the ring is 1 or 2
C₁~ C_ThreeAlkyl group, one C₁~ C_ThreeAlkoxy
Group, one (C₁~ C_ThreeAlkoxy) C₁~ C_ThreeAlkoxy
Group, one di (C₁~ C_ThreeAlkyl) amino group, one d
A tylenedioxy group, one trimethylenedioxy group or
One N- (C₁~ C_ThreeSubstituted by an (alkoxy) imino group
Wherein at any position the ring is oxygen, sulfur or
Formula NR^6bA group represented by the formula:^6bIs C₁~ C_ThreeArchi
Represents a hydroxyl group. ). ｝,
Even more preferably, the same or different, C₁~ C_TwoArchi
Or a group represented by R ^TwoAnd R^ThreeAre they combined
Together with the carbon atom
The chlorohexane ring has one or two C₁~ C_TwoAlkyl group,
One C₁~ C_TwoAn alkoxy group, one (C₁~ C_TwoArco
Kishi) C₁~ C_TwoAlkoxy group, one ethylenedioxy
Group, one trimethylenedioxy group or one N- (C
₁~ C_TwoIt may be substituted by an (alkoxy) imino group. ｝
And particularly preferably both represent a methyl group, or
R^TwoAnd R^ThreeTogether with the carbon atom to which they are attached
The cyclohexane ring ｛the cyclohexane ring is
One C₁~ C_TwoAlkoxy group, ethylenedioxy group,
Rimethylenedioxy group or N- (C₁~ C_TwoAlkoxy)
It may be substituted by an imino group. ｝ And most preferably
Both represent a methyl group, or R^TwoAnd R^ThreeIs it
Together with the carbon atom to which they are attached
It is a cyclohexane ring.

In the present invention, R^FourIs preferably hydrogen
Atom, C_Two~ C₈Alkylcarbonyl group (the alkyl
A rubonyl group has 1 to 3 chlorine atoms or fluorine atoms.
Or bromine atom, one C_Two~ C_FiveAlkylcarbonyloxy
Si group, one C₁~ C_FourAlkoxy group or one phenoxy
It may be substituted by a group. ), C_Four~ C₇Cycloalkyl
Carbonyl group ｛The cycloalkylcarbonyl group is
C₁~ C_FourAlkyl group, chlorine atom, fluorine atom and bromine atom
1 to 4 substituents selected from the group consisting of
Two C₁~ C_FourAn alkoxy group, one or two cyano groups or
Is one phenyl group (the phenyl group is one C₁~
C_FourIt may be substituted by an alkoxy group. Replaced by)
May be. ｝, C_Three~ C₆Alkenylcarbonyl group (this
The alkenylcarbonyl group has 1 to 3 chlorine atoms,
It may be substituted by a fluorine atom or a bromine atom. ), Ba
Benzoyl group: The benzoyl group is a chlorine atom,
Child, bromine atom and C₁~ C_FourAlkyl group (the alkyl group
Is one to three chlorine atoms, fluorine atoms or bromine atoms
Or a phenoxy group. ) Or
1 to 3 substituents selected from the group consisting of 1 to 3
C₁~ C_FourAn alkoxy group, one C_Two~ C_FiveAlkyl cal
Bonyloxy group, one C_Two~ C_FiveAlkoxycarbonyl
Group, one C₁~ C_FourAlkylthio group, one C₁~ C_FourA
Rukylsulfinyl group, one C₁~ C_FourAlkylsulfo
Nil group, one phenoxy group, one cyano group or one
May be substituted by a nitro group. ｝ 4- to 6-member complex
Ring carbonyl group ｛the heterocyclic carbonyl group is 1 to 3
Containing one oxygen atom, sulfur atom or nitrogen atom,
Two C₁~ C_FourAlkyl group (the alkyl group is 1 to
Replaced by three chlorine, fluorine or bromine atoms
May be. ) One or two C₁~ C_FourAlkoxy group, 1
C₁~ C_FourAn alkylthio group or one chlorine atom,
May be substituted by a hydrogen atom or a bromine atom,
And it may be condensed with a ring. ｝, C_Two~ C₈Alkoxycarbo
Nil group—the alkoxycarbonyl group has 1 to 3
Chlorine atom, fluorine atom or bromine atom, one C₁~
C_FourAn alkoxy group, one C₁~ C_FourAlkylthio group, 1
Phenyl groups (the phenyl group is a chlorine atom, fluorine
Atom, bromine atom and C₁~ C_FourFrom the group consisting of alkyl groups
It may be substituted by one to three selected substituents. )
Or one 5- or 6-membered heterocyclic group (the heterocyclic group is
Contains 1 to 3 oxygen, sulfur or nitrogen atoms
And chlorine, fluorine, bromine and C₁~ C_FourAl
With one or two substituents selected from the group consisting of
May be replaced. ). ｝, C _Five
~ C₇Cycloalkoxycarbonyl group, C_Four~ C₇Arche
Nyloxycarbonyl group, C_Four~ C₇Alkynyloxyca
Rubonyl group, (C₁~ C_FourAlkylthio) carbonyl group,
(Phenylthio) carbonyl group カ ル ボ ニ ル the (phenylthio)
The carbonyl group is a chlorine atom, a fluorine atom, a bromine atom and
C₁~ C_Four1 to 3 selected from the group consisting of alkyl groups
May be substituted. ｝, (C₁~ C_FourArco
(Xy) thiocarbonyl group, (phenoxy) thiocarboni
The (phenoxy) thiocarbonyl group is a chlorine atom
Atom, fluorine atom, bromine atom and C₁~ C_FourFrom an alkyl group
Substituted with one to three substituents selected from the group consisting of
May be. ｝, C_Two~ C₆Alkyldithiocarbonyl group,
Enyldithiocarbonyl group (the phenyldithiocarbo
Nyl group is a chlorine atom, a fluorine atom, a bromine atom and C₁~
C_Four1 to 3 positions selected from the group consisting of alkyl groups
It may be substituted by a substituent. ), C₁~ C_FourAlkyl group
｛The alkyl group is a phenyl group (the phenyl group)
Is a chlorine atom, a fluorine atom, a bromine atom,₁~ C_FourA
Alkyl group and C₁~ C_FourSelected from the group consisting of alkoxy groups
May be substituted by one to three substituents. ), C
₁~ C_FourAn alkoxy group, (C₁~ C_FourAlkoxy) C₁~ C_Four
Alkoxy group, C₁~ C_FourAlkylthio group, cyano group,
Phenoxy group (the phenoxy group is a chlorine atom,
Child, bromine atom and C₁~ C_FourSelect from the group consisting of alkyl groups
It may be substituted by 1 to 3 substituents. )or
Is C_Two~ C_FiveSubstituted by an alkoxycarbonyl group
No. ｝, C_Three~ C_FiveAlkenyl group, C_Three~ C_FiveAlkynyl
Group, di (C₁~ C_FourAlkyl) carbamoyl group
The two alkyl groups in the lkylcarbamoyl are
5- or 6-membered heterocycle together with the nitrogen atom to which it is attached
(The heterocycle has one nitrogen atom and one oxygen atom.
Or it may contain a nitrogen atom. ) May be formed. ｝,
Di (C₁~ C_FourAlkyl) thiocarbamoyl group ｛the dia
The two alkyl groups in the alkylthiocarbamoyl are
5 or 6 membered together with the nitrogen atom to which they
An elementary ring (the heterocycle is one nitrogen atom and one oxygen atom
It may contain atoms or nitrogen atoms. Form)
No. ｝, C₁~ C_FourAlkylsulfonyl group, phenylsulfur
Honyl group (the phenylsulfonyl group is a chlorine atom,
Nitrogen atom, bromine atom and C₁~ C_FourGroup consisting of alkyl groups
Substituted with 1 to 3 substituents selected from
No. ) Or di (C₁~ C_FourAlkoxy) thiophosphoryl group
And more preferably a hydrogen atom, C_Two~ C₆Alkylka
Rubonyl group (1 to 3 alkylcarbonyl groups
Chlorine or fluorine atom, one C_Two~ C_FourArchi
Carbonyloxy group, one C₁~ C_ThreeAlkoxy group or
May be substituted by one phenoxy group. ), C_Four
~ C₇Cycloalkylcarbonyl group ｛the cycloalkyl
Carbonyl group is one to four C₁~ C_ThreeAlkyl group,
Chlorine atom or fluorine atom, one C₁~ C_ThreeAlkoki
Group, one cyano group or one phenyl group (the
The nil group has one C₁~ C_ThreeSubstituted by an alkoxy group
May be. ). ｝, C_Three~ C_FiveArche
Carbonyl group (the alkenylcarbonyl group is 1
Or two substituted by chlorine or fluorine atoms
No. ), Benzoyl group ｛The benzoyl group is a chlorine atom
Atom, fluorine atom and C₁~ C_ThreeAlkyl group (the alkyl
The group is 1 to 3 chlorine or fluorine atoms or 1
Phenoxy groups. Group consisting of)
1 or 2 substituents selected from 1 or 2 C₁~
C_ThreeAn alkoxy group, one C_Two~ C_FourAlkylcarbonyl
An oxy group, one C_Two~ C_FourAlkoxycarbonyl group, 1
C₁~ C_ThreeAlkylthio group, one C₁~ C_ThreeAlkyl
Sulfinyl group, one C₁~ C_ThreeAlkylsulfonyl
Group, one phenoxy group, one cyano group or one
It may be substituted by a toro group. ｝ 4- to 6-membered heterocyclic ring
Rubonyl group—the heterocyclic carbonyl group has 1 to 3
Containing 1 or 2 oxygen, sulfur or nitrogen atoms
C₁~ C_ThreeAlkyl group (1 to 3 alkyl groups
May be substituted by a chlorine atom or a fluorine atom. ),
One or two C₁~ C_ThreeAn alkoxy group, one C₁~ C_ThreeA
Alkylthio or one chlorine or fluorine atom
And may be condensed with a benzene ring.
No. ｝, C_Two~ C₈Alkoxycarbonyl group ｛the alcohol
An oxycarbonyl group is one to three chlorine atoms or
Nitrogen atom, one C₁~ C_ThreeAn alkoxy group, one C₁~
C_ThreeAn alkylthio group, one phenyl group or one
Or a 6-membered heterocyclic group (the heterocyclic group is one or two acids
Contains elemental or nitrogen atoms. )
No. ｝, C₆~ C₇Cycloalkoxycarbonyl group, C_Four
~ C₆Alkenyloxycarbonyl group, C_Four~ C₆Archi
Nyloxycarbonyl group, (C₁~ C_ThreeAlkylthio) ka
Rubonyl group, (phenylthio) carbonyl group, (C₁~
C_ThreeAlkoxy) thiocarbonyl group, (phenoxy) thio
Ocarbonyl group, C_Two~ C_FiveAlkyldithiocarbonyl
Group, phenyldithiocarbonyl group, C₁~ C_ThreeAlkyl group
{The alkyl group is one phenyl group, C₁~ C_ThreeA
Alkoxy group, (C₁~ C_ThreeAlkoxy) C₁~ C_ThreeAlkoki
Si group, C₁~ C_ThreeAlkylthio group, cyano group, phenoxy
Group or C_Two~ C_FourSubstituted by an alkoxycarbonyl group
May be. ｝, C_Three~ C_FourAlkenyl group, C_Three~ C_FourAlkini
Lu group, di (C₁~ C_ThreeAlkyl) carbamoyl group
The two alkyl groups in the alkylcarbamoyl are
Is a 5- or 6-membered complex together with the nitrogen atom to which
Ring (the heterocycle is one nitrogen atom and one oxygen atom
May contain atoms or nitrogen atoms. Form)
No. ｝, J (C₁~ C_ThreeAlkyl) thiocarbamoyl group
２Two alkyls in the dialkylthiocarbamoyl
The groups together with the nitrogen atom to which they are attached
Or a 6-membered heterocyclic ring (the heterocyclic ring is, in addition to one nitrogen atom,
It may contain one oxygen or nitrogen atom. Form)
May do it. ｝, C₁~ C_ThreeAlkylsulfonyl group, phenyl
Rusulfonyl group or di (C₁~ C_ThreeAlkoxy) thiophos
And more preferably a hydrogen atom, C_Two~
C_FourAlkylcarbonyl group, cyclopropylcarbonyl
Group (the cyclopropylcarbonyl group is one C₁~
C_TwoIt may be substituted by an alkyl group. ), C_Three~ C_FourA
Lucenylcarbonyl group, benzoyl group or C_Two~ C_ThreeAl
A oxycarbonyl group, particularly preferably a hydrogen atom,
C_Two~ C_FourAlkylcarbonyl group, cyclopropylcarbo
Group (the cyclopropylcarbonyl group is one
It may be substituted by a tyl group. ) Or C_Two~ C_ThreeAlkoki
It is a cyclocarbonyl group.

In the present invention, A is preferably C₁~
C_FourAn alkyl group (where the alkyl group is 1 to 5 chlorine atoms)
Atom, fluorine atom or bromine atom
No. ), Chlorine atom, fluorine atom, bromine atom, C₁~ C_FourA
Alkoxy group (the alkoxy group is one to three chlorine atoms
Substituted by a fluorine atom, a fluorine atom or a bromine atom
No. ), C ₁~ C_FourAlkylthio group, C₁~ C_FourAlkyls
Ruphonyl group, phenyl group (the phenyl group is a chlorine atom
Atom, fluorine atom, bromine atom and C₁~ C_FourFrom an alkyl group
Substituted with one to three substituents selected from the group consisting of
May be. ) 5- or 6-membered heterocyclic group (the heterocyclic group
Contains one to three oxygen, sulfur or nitrogen atoms.
Having a chlorine atom, a fluorine atom, a bromine atom and C₁~ C_FourA
One or two substituents selected from the group consisting of
More may be substituted. ), Cyano group, nitro group, amino
Group or phenoxy group (the phenoxy group is a chlorine atom,
Fluorine atom, bromine atom and C₁~ C_FourConsists of an alkyl group
Substituted with 1 to 3 substituents selected from the group.
No. ), And more preferably C₁~ C_ThreeAlkyl group (this
The alkyl group has 1 to 3 chlorine atoms or fluorine atoms.
May be replaced by ), Chlorine atom, fluorine atom, smell
Elementary atom, C₁~ C_ThreeAlkoxy group, C₁~ C_ThreeAlkylthio
Group, C₁~ C_ThreeAlkylsulfonyl group, phenyl group, 5
Or a 6-membered heterocyclic group (the heterocyclic group is one or two acids
Contains elemental or nitrogen atoms. ), Cyano group, nitro
Group, amino group or phenoxy group, even more preferably
Is a methyl group or a chlorine atom, and particularly preferably, methyl
Group.

In the present invention, n is preferably 2 or 3. In particular, the substitution position of the substituent A is 2,4-, 2,
6-, 2,3,6- or 2,4,6- are preferred.

In the present invention, X is preferably an oxygen atom or a sulfur atom, and more preferably an oxygen atom.

When the compound (I) of the present invention has a hydroxyl group in the molecule, it can be converted into, for example, an alkali metal salt, an alkaline earth metal salt or an ammonium salt, and has a basic moiety in the molecule. In such a case, for example, salts such as sulfates, hydrochlorides, nitrates, and phosphates can be used.
These salts are included in the present invention as long as they can be used as agricultural and horticultural herbicides.

In the present invention, the “alkali metal salt” includes, for example, a sodium salt, a potassium salt and a lithium salt, and is preferably a sodium salt or a potassium salt.

In the present invention, “alkaline earth metal salt”
"" Means, for example, a calcium salt and a magnesium salt, preferably a calcium salt.

Hydrates of the compound of the present invention are also included in the present invention.

The compounds of the present invention include compounds having an asymmetric carbon atom. In such a case, the present invention includes a mixture of one kind of optically active substance and several kinds of optically active substances at an arbitrary ratio. .

Compound (I) of the present invention is preferably (a)
Is R¹Is a hydrogen atom, C₁~ C_FourAlkyl group
The kill group is one C_Three~ C₇A cycloalkyl group, one
Phenyl group (the phenyl group is a chlorine atom, a fluorine atom,
Bromine atom and C₁~ C_FourSelected from the group consisting of alkyl groups
May be substituted by one to three substituents. )
Is two C₁~ C_FourAn alkoxy group (the alkoxy group is
From 1 to 5 chlorine, fluorine or bromine atoms
It may be replaced. ) One C_Three~ C_FiveAlkenyloxy
Group, one (C₁~ C_FourAlkoxy) C₁~ C_FourAlkoxy
Group, one benzyloxy group, one C₁~ C_FourAlkyl
Thio group, 1 to 3 chlorine atoms, fluorine atoms or odors
One atom, one cyano group, one di (C₁~ C_FourArchi
L) an amino group or one 5- or 6-membered heterocyclic group
A heterocyclic group has 1 to 3 oxygen atoms, sulfur atoms or nitrogen
Containing atoms, chlorine, fluorine, bromine and C
₁~ C_FourAn alkyl group (where the alkyl group is one to three salts
Substituted by a fluorine atom, a fluorine atom or a bromine atom
No. 1) or 2 substituents selected from the group consisting of
May be replaced. May be replaced by｝. 》, C_Three
~ C₇Cycloalkyl group, C_Three~ C_FiveAlkenyl groups (such
An alkenyl group has 1 to 3 chlorine atoms, fluorine atoms or
May be replaced by a bromine atom. ), C_Three~ C_FiveArchi
Phenyl group, phenyl group (the phenyl group is a chlorine atom,
Nitrogen atom, bromine atom and C₁~ C_FourGroup consisting of alkyl groups
Substituted with 1 to 3 substituents selected from
No. 5) or 6-membered heterocyclic group {the heterocyclic group is 1
Containing 3 to 3 oxygen, sulfur or nitrogen atoms,
One C₁~ C_FourAlkyl group (the alkyl group is 1 to
Replaced by three chlorine, fluorine or bromine atoms
May be. ). ｝, C_Two~ C₈Al
A kill carbonyl group (the alkylcarbonyl group is
Up to three chlorine, fluorine or bromine atoms, one
C₁~ C_FourBy an alkoxy group or one phenoxy group
It may be replaced. ), Benzoyl group (the benzoyl group
Is a chlorine atom, a fluorine atom, a bromine atom and C₁~ C_FourAl
1 to 3 substituents selected from the group consisting of
May be replaced. ), C_Two~ C_FiveAlkoxycarbonyl
Group, di (C₁~ C_FourAlkyl) carbamoyl group, C₁~ C_Four
An alkylsulfonyl group or a phenylsulfonyl group (the
Phenylsulfonyl group is chlorine atom, fluorine atom, bromine
Atom and C₁~ C_Four1 selected from the group consisting of alkyl groups
It may be substituted with up to 3 substituents. ) And R
^TwoAnd R^ThreeAre the same or different and C₁~ C_FourAlkyl group
{The alkyl group has one C_Three~ C₇Cycloalkyl
Group, one phenyl group (the phenyl group is a chlorine atom,
Fluorine atom, bromine atom, C₁~ C_FourAlkyl group and C₁~
C_Four1 to 3 members selected from the group consisting of alkoxy groups
It may be substituted by a substituent. ) One or two C₁~
C_FourAn alkoxy group, one (C₁~ C_FourAlkoxy) C₁~
C_FourAlkoxy group, 1 to 5 chlorine atoms, fluorine atoms
Or a bromine atom or one 5- or 6-membered heterocyclic group
(The heterocyclic group has 1 to 3 oxygen atoms, sulfur atoms or
Contains a nitrogen atom. ). ｝,
C_Three~ C₇Cycloalkyl group, C_Three~ C_FiveAlkenyl group (this
The alkenyl group has 1 to 3 chlorine atoms, fluorine atoms
Or it may be substituted by a bromine atom. ), C_Three~ C_FiveAl
Quinyl group, phenyl group (the phenyl group is a chlorine atom,
Fluorine atom, bromine atom, C₁~ C_FourAlkyl group and C ₁~
C_Four1 to 3 members selected from the group consisting of alkoxy groups
It may be substituted by a substituent. ) Or 5 or 6 members
A heterocyclic group ｛the heterocyclic group has 1 to 3 oxygen atoms,
Atom or nitrogen atom, chlorine atom, fluorine atom, odor
Elementary atom and C₁~ C_FourAlkyl group (the alkyl group is 1
From 3 to 3 chlorine, fluorine or bromine atoms
May be replaced. )) Or one or two selected from the group consisting of
It may be substituted by a substituent. Represents｝, or R^TwoPassing
And R^ThreeTogether with the carbon atom to which they are attached
4 to 7 membered cycloalkane, cycloalkene
Or 1 to 3 cycloalkanediene rings
C₁~ C_FourAlkyl group, one C₁~ C_FourAn alkoxy group,
One (C₁~ C_FourAlkoxy) C₁~ C_FourAn alkoxy group,
One di (C₁~ C_FourAlkyl) amino group, one methyle
Dioxy group, one ethylene dioxy group, one tri
A methylenedioxy group or one N- (C₁~ C_FourAlkoki
B) may be substituted by an imino group,
Oxygen atom, sulfur atom or formula NR^6aA group represented by the formula (wherein
R^6aIs C₁~ C_FourRepresents an alkyl group. Interrupted by
May be. ｝ And R^FourIs a hydrogen atom, C_Two~ C₈A
Alkylcarbonyl group (the alkylcarbonyl group is 1
3 to 3 chlorine, fluorine or bromine atoms, 1
C_Two~ C_FiveAlkylcarbonyloxy group, one C₁
~ C_FourSubstituted by an alkoxy group or one phenoxy group
May be. ), C_Four~ C₇Cycloalkylcarbonyl group
{The cycloalkylcarbonyl group is C₁~ C_FourArchi
Or a group consisting of chlorine, chlorine, fluorine and bromine
1 to 4 substituents selected from 1 or 2 C₁~ C_Four
An alkoxy group, one or two cyano groups or one phenyl
Group (the phenyl group has one C₁~ C_FourAlkoxy group
May be replaced by ). ｝,
C_Three~ C₆Alkenylcarbonyl group (the alkenylcal
A bonyl group has 1 to 3 chlorine atoms, fluorine atoms or odors.
It may be substituted by an elementary atom. ), Benzoyl group
Benzoyl groups are chlorine, fluorine, bromine and
C₁~ C_FourAn alkyl group (where the alkyl group is
Chlorine atom, fluorine atom or bromine atom or one
It may be substituted by a nonoxy group. Selected from the group consisting of
1 to 3 substituents, 1 to 3 C₁~ C_FourArco
Xyl group, one C_Two~ C_FiveAlkylcarbonyloxy group,
One C_Two~ C_FiveAn alkoxycarbonyl group, one C₁~
C_FourAlkylthio group, one C₁~ C_FourAlkylsulfi
Nyl group, one C₁~ C_FourAlkylsulfonyl group, one
A phenoxy group, one cyano group or one nitro group
May be replaced. ｝ 4- to 6-membered heterocyclic carbonyl group
｛The heterocyclic carbonyl group has 1 to 3 oxygen atoms,
Containing a sulfur or nitrogen atom and containing 1 or 2 carbon atoms₁~ C_Four
An alkyl group (the alkyl group is one to three chlorine atoms)
Substituted by a fluorine atom, a fluorine atom or a bromine atom
No. ) One or two C₁~ C_FourAn alkoxy group, one C
₁~ C_FourAlkylthio group or one chlorine atom or fluorine atom
Or it may be substituted by a bromine atom,
It may be condensed. ｝, C_Two~ C₈Alkoxycarbonyl group
｛The alkoxycarbonyl group has 1 to 3 chlorine atoms.
Atom, fluorine atom or bromine atom, one C₁~ C_FourAl
Coxy group, one C₁~ C_FourAlkylthio group, one
Nil group (the phenyl group is a chlorine atom, a fluorine atom,
Elementary atom and C₁~ C_FourSelected from the group consisting of alkyl groups
It may be substituted by 1 to 3 substituents. ) Or one
A 5- or 6-membered heterocyclic group (the heterocyclic group is 1 to 3
Containing oxygen, sulfur or nitrogen atoms
Atom, fluorine atom, bromine atom and C₁~ C_FourFrom an alkyl group
Substituted by one or two substituents selected from the group consisting of
May be. ). ｝, C_Five~ C₇Cyclo
Alkoxycarbonyl group, C_Four~ C₇Alkenyloxyca
Rubonyl group, C_Four~ C₇Alkynyloxycarbonyl group,
(C₁~ C_FourAlkylthio) carbonyl group, (phenylthio)
E) carbonyl group ｛the (phenylthio) carbonyl group
Is a chlorine atom, a fluorine atom, a bromine atom and C₁~ C_FourAl
1 to 3 substituents selected from the group consisting of
May be replaced. ｝, (C₁~ C_FourAlkoxy) thioca
Rubonyl group, (phenoxy) thiocarbonyl group
(Phenoxy) thiocarbonyl group is chlorine atom, fluorine
Atom, bromine atom and C₁~ C_FourFrom the group consisting of alkyl groups
Substituted with one to three selected substituents.
No. ｝, C_Two~ C₆Alkyldithiocarbonyl group, phenyl
Rudithiocarbonyl group (the phenyldithiocarbonyl
Groups are chlorine, fluorine, bromine and C₁~ C_FourA
1 to 3 substituents selected from the group consisting of
More may be substituted. ), C₁~ C_FourAlkyl group
The alkyl group is one phenyl group (the phenyl group is
Chlorine atom, fluorine atom, bromine atom, C₁~ C_FourAlkyl group
And C₁~ C_Four1 selected from the group consisting of alkoxy groups
It may be substituted by up to three substituents. ), C₁~ C_FourA
Alkoxy group, (C₁~ C_FourAlkoxy) C₁~ C_FourAlkoki
Si group, C₁~ C_FourAlkylthio group, cyano group, phenoxy
Group (the phenoxy group is a chlorine atom, a fluorine atom, a bromine
Atom and C₁~ C_Four1 selected from the group consisting of alkyl groups
It may be substituted with up to 3 substituents. ) Or C_Two~
C_FiveSubstituted by an alkoxycarbonyl group
No. ｝, C_Three~ C_FiveAlkenyl group, C_Three~ C_FiveAlkynyl
Group, di (C₁~ C_FourAlkyl) carbamoyl group
The two alkyl groups in the lkylcarbamoyl are
5- or 6-membered heterocycle together with the nitrogen atom to which it is attached
(The heterocycle has one nitrogen atom and one oxygen atom.
Or it may contain a nitrogen atom. ) May be formed. ｝,
Di (C₁~ C_FourAlkyl) thiocarbamoyl group ｛the dia
The two alkyl groups in the alkylthiocarbamoyl are
5 or 6 membered together with the nitrogen atom to which they
An elementary ring (the heterocycle is one nitrogen atom and one oxygen atom
It may contain atoms or nitrogen atoms. Form)
No. ｝, C₁~ C_FourAlkylsulfonyl group, phenylsulfur
Honyl group (the phenylsulfonyl group is a chlorine atom,
Nitrogen atom, bromine atom and C₁~ C_FourGroup consisting of alkyl groups
Substituted with 1 to 3 substituents selected from
No. ) Or di (C₁~ C_FourAlkoxy) thiophosphoryl group
And A is C₁~ C_FourAlkyl group (the alkyl group
Represents 1 to 5 chlorine, fluorine or bromine atoms
More may be substituted. ), Chlorine atom, fluorine atom, bromine
Atom, C₁~ C_FourAn alkoxy group (the alkoxy group is 1
From 3 to 3 chlorine, fluorine or bromine atoms
May be replaced. ), C₁~ C_FourAlkylthio group, C₁~ C_Four
Alkylsulfonyl group, phenyl group (the phenyl group
Is a chlorine atom, a fluorine atom, a bromine atom and C₁~ C_FourAl
1 to 3 substituents selected from the group consisting of
May be replaced. ) 5- or 6-membered heterocyclic group (
A heterocyclic group has 1 to 3 oxygen atoms, sulfur atoms or nitrogen
Containing atoms, chlorine, fluorine, bromine and C
₁~ C_FourOne or two selected from the group consisting of alkyl groups
It may be substituted by a substituent. ), Cyano group, nitro
Group, amino group or phenoxy group (the phenoxy group is
Chlorine atom, fluorine atom, bromine atom and C₁~ C_FourAlkyl
With one to three substituents selected from the group consisting of
May be replaced. And n is 1, 2, 3, 4 or 5
X is an oxygen atom, a sulfur atom, a sulfinyl group or
Is a compound that is a sulfonyl group, more preferably (b)
Is R¹Is a hydrogen atom, C₁~ C_ThreeAlkyl group ｛Al
The kill group is one C_Three~ C₆A cycloalkyl group, one
Enyl group, one or two C₁~ C_ThreeAn alkoxy group
The alkoxy group is substituted with one to three chlorine or fluorine atoms.
More may be substituted. ), One (C₁~ C_ThreeAlkoki
C) C₁~ C_ThreeAn alkoxy group, one benzyloxy group,
One C₁~ C_ThreeAlkylthio group, 1 to 3 chlorine atoms
Or a fluorine atom, one cyano group or one 5 or less
Or a 6-membered heterocyclic group (the heterocyclic group is one or two oxygen atoms
Contains atoms or nitrogen atoms. )
No. ｝, C_Three~ C₆Cycloalkyl group, C_Three~ C_FourAlkene
(The alkenyl group is one or two chlorine atoms or
It may be substituted by a fluorine atom. ), C_Three~ C_FourArchi
A phenyl group, a 5- or 6-membered heterocyclic group (the
The ring group contains one or two oxygen or nitrogen atoms
You. ), C_Two~ C₆Alkylcarbonyl group, benzoyl
Group, C_Two~ C_FourAn alkoxycarbonyl group, di (C₁~ C_ThreeA
Alkyl) carbamoyl group, C₁~ C_ThreeAlkylsulfonyl
Or a phenylsulfonyl group,^TwoAnd R^ThreeBut the same
One or different, C₁~ C_ThreeAlkyl group ｛The alkyl group
Is one C_Three~ C₆Cycloalkyl group, one phenyl
Group (the phenyl group is a chlorine atom, a fluorine atom,₁~
C_ThreeAlkyl group and C₁~ C_ThreeGroup consisting of alkoxy groups
Substituted by one or two substituents selected from
No. ) One or two C₁~ C_ThreeAn alkoxy group, one
(C₁~ C_ThreeAlkoxy) C₁~ C_ThreeAlkoxy group, 1 to
3 chlorine or fluorine atoms or 1 5
Is a 6-membered heterocyclic group (the heterocyclic group is one or two oxygen atoms)
Contains a nitrogen atom or a nitrogen atom. )
No. ｝, C_Three~ C₆Cycloalkyl group, C_Three~ C_FourAlkene
Group, C_Three~ C_FourAlkynyl group, phenyl group (the phenyl
A 1 or 2 C₁~ C_ThreeSubstituted by alkoxy group
May be. ) Or a 5- or 6-membered heterocyclic group
Ring groups contain one or two oxygen or nitrogen atoms
You. ) Or R^TwoAnd R^ThreeAre they combined
Together with the carbon atoms that are present
Lucane, cycloalkene or cycloalkanediene
Ring—the ring has one or two C₁~ C_ThreeOne alkyl group
C₁~ C_ThreeAn alkoxy group, one (C₁~ C_ThreeAlkoki
C) C₁~ C_ThreeAn alkoxy group, one di (C₁~ C_ThreeArchi
L) an amino group, one ethylenedioxy group, one tri
A methylenedioxy group or one N- (C₁~ C_ThreeAlkoki
B) may be substituted by an imino group,
Oxygen atom, sulfur atom or formula NR^6bA group represented by the formula (wherein
R^6bIs C₁~ C_ThreeRepresents an alkyl group. Interrupted by
May be. ｝ And R^FourIs a hydrogen atom, C_Two~ C₆A
Alkylcarbonyl group (the alkylcarbonyl group is 1
1 to 3 chlorine or fluorine atoms, 1 C_Two~
C_FourAlkylcarbonyloxy group, one C₁~ C_ThreeAl
Substituted by a oxy group or one phenoxy group.
No. ), C_Four~ C₇Cycloalkylcarbonyl group
A chloroalkylcarbonyl group has 1 to 4 C₁~ C_ThreeA
Alkyl group, chlorine atom or fluorine atom, one C₁~
C_ThreeAn alkoxy group, one cyano group or one phenyl
Group (the phenyl group has one C₁~ C_ThreeTo the alkoxy group
More may be substituted. ). ｝, C
_Three~ C_FiveAlkenylcarbonyl group (the alkenylcarbo group
A nyl group is represented by one or two chlorine or fluorine atoms
It may be replaced. ), Benzoyl group ｛the benzoyl group
Is a chlorine atom, a fluorine atom and C₁~ C_ThreeAlkyl group (this
The alkyl group has 1 to 3 chlorine atoms or fluorine.
It may be substituted by an atom or one phenoxy group. )
1 or 2 substituents selected from the group consisting of
C₁~ C_ThreeAn alkoxy group, one C_Two~ C_FourAlkylka
Rubonyloxy group, one C_Two~ C_FourAlkoxycarboni
Group, one C₁~ C_ThreeAlkylthio group, one C₁~ C_Three
Alkylsulfinyl group, one C₁~ C_ThreeAlkylsul
A honyl group, one phenoxy group, one cyano group or one
Nitro groups. ｝ 4 to 6 members
A heterocyclic carbonyl group—the heterocyclic carbonyl group is 1 to
Containing three oxygen, sulfur or nitrogen atoms and containing one or
Is two C₁~ C_ThreeAn alkyl group (the alkyl group is
Substituted with up to three chlorine or fluorine atoms
No. ) One or two C₁~ C_ThreeAn alkoxy group, one C
₁~ C_ThreeAn alkylthio group or one chlorine atom or
May be substituted by an elemental atom, even when condensed with a benzene ring.
Good. ｝, C_Two~ C₈Alkoxycarbonyl group ｛
A oxycarbonyl group has 1 to 3 chlorine atoms or
Fluorine atom, one C₁~ C_ThreeAn alkoxy group, one C₁
~ C_ThreeAn alkylthio group, one phenyl group or one 5
Or a 6-membered heterocyclic group (the heterocyclic group comprises one or two
Contains oxygen or nitrogen atoms. ) Replaced by
Good. ｝, C₆~ C₇Cycloalkoxycarbonyl group, C
_Four~ C₆Alkenyloxycarbonyl group, C_Four~ C₆Archi
Nyloxycarbonyl group, (C₁~ C_ThreeAlkylthio) ka
Rubonyl group, (phenylthio) carbonyl group, (C₁~
C_ThreeAlkoxy) thiocarbonyl group, (phenoxy) thio
Ocarbonyl group, C _Two~ C_FiveAlkyldithiocarbonyl
Group, phenyldithiocarbonyl group, C₁~ C_ThreeAlkyl group
{The alkyl group is one phenyl group, C₁~ C_ThreeA
Alkoxy group, (C₁~ C_ThreeAlkoxy) C₁~ C_ThreeAlkoki
Si group, C₁~ C_ThreeAlkylthio group, cyano group, phenoxy
Group or C_Two~ C_FourSubstituted by an alkoxycarbonyl group
May be. ｝, C_Three~ C_FourAlkenyl group, C_Three~ C_FourAlkini
Lu group, di (C₁~ C_ThreeAlkyl) carbamoyl group
The two alkyl groups in the alkylcarbamoyl are
Is a 5- or 6-membered complex together with the nitrogen atom to which
Ring (the heterocycle is one nitrogen atom and one oxygen atom
May contain atoms or nitrogen atoms. Form)
No. ｝, J (C₁~ C_ThreeAlkyl) thiocarbamoyl group
２Two alkyls in the dialkylthiocarbamoyl
The groups together with the nitrogen atom to which they are attached
Or a 6-membered heterocyclic ring (the heterocyclic ring is, in addition to one nitrogen atom,
It may contain one oxygen or nitrogen atom. Form)
May do it. ｝, C₁~ C_ThreeAlkylsulfonyl group, phenyl
Rusulfonyl group or di (C₁~ C_ThreeAlkoxy) thiophos
A phosphoryl group, A is C₁~ C_ThreeAlkyl group
A kill group is formed by one to three chlorine or fluorine atoms.
It may be replaced. ), Chlorine atom, fluorine atom, bromine atom
Child, C₁~ C_ThreeAlkoxy group, C₁~ C_ThreeAlkylthio group,
C₁~ C_ThreeAlkylsulfonyl group, phenyl group, 5 or more
Is a 6-membered heterocyclic group (the heterocyclic group is one or two oxygen atoms)
Contains a nitrogen atom or a nitrogen atom. ), Cyano, nitro,
An amino group or a phenoxy group, wherein n is 1, 2, 3,
4 or 5, wherein X is an oxygen atom or a sulfur atom
And (c) even more preferably R¹But C₁~ C
_TwoAlkyl group—the alkyl group has one C₁~ C_TwoAl
Coxy group, one (C₁~ C_TwoAlkoxy) C₁~ C_TwoAl
Coxy group or one C₁~ C_TwoSubstituted by alkylthio group
May be. ｝ And R^TwoAnd R^ThreeBut the same or different
And C₁~ C_TwoRepresents an alkyl group, or R^TwoAnd R^ThreeIs
Together with the carbon atom to which they are attached, cyclo
Hexane ring—The cyclohexane ring has one or two C
₁~ C_TwoAlkyl group, one C₁~ C_TwoOne alkoxy group
(C₁~ C_TwoAlkoxy) C₁~ C_TwoOne alkoxy group
Ethylenedioxy group, one trimethylenedioxy group
Or one N- (C₁~ C_TwoBy an alkoxy) imino group
It may be replaced. ｝ And R^FourIs a hydrogen atom, C_Two~ C
_FourAlkylcarbonyl group, cyclopropylcarbonyl group
(The cyclopropylcarbonyl group has one C₁~ C_Two
It may be substituted by an alkyl group. ), C_Three~ C_FourArche
Nilcarbonyl group, benzoyl group or C_Two~ C_ThreeAlkoki
A cyclocarbonyl group, wherein A is a methyl group or a chlorine atom
Wherein n is 2 or 3 and X is an oxygen atom or sulfur
A compound that is an atom, and (d) particularly preferably
¹But C₁~ C_TwoAn alkyl group (the alkyl group is
C₁~ C_TwoIt may be substituted by an alkoxy group. )
R^TwoAnd R^ThreeRepresents a methyl group, or R^Two
And R^ThreeTogether with the carbon atom to which they are attached
Thus, the cyclohexane ring ｛the cyclohexane ring is 1
C₁~ C_TwoAlkoxy group, ethylenedioxy group, tri
Methylenedioxy group or N- (C₁~ C_TwoAlkoxy) i
It may be substituted by a amino group. ｝ And R^FourBut hydrogen
Atom, C_Two~ C_FourAlkylcarbonyl group, cyclopropyl
A carbonyl group (the cyclopropylcarbonyl group is 1
May be substituted by methyl groups. ) Or C_Two~ C_ThreeA
A carbonyloxy group, A is a methyl group,
n is 2 or 3, and X is an oxygen atom or a sulfur atom
A certain compound.

Compound (II) of the present invention is preferably (a ')
Has R¹Is a hydrogen atom, C₁~ C_FourAlkyl group <
The alkyl group has one C_Three~ C₇Cycloalkyl group, one
Phenyl group (the phenyl group is a chlorine atom,
Child, bromine atom and C₁~ C_FourSelect from the group consisting of alkyl groups
It may be substituted by 1 to 3 substituents. ),
One or two C₁~ C_FourAn alkoxy group (the alkoxy group
Represents 1 to 5 chlorine, fluorine or bromine atoms
More may be substituted. ) One C_Three~ C_FiveAlkenylo
Xyl group, one (C₁~ C_FourAlkoxy) C₁~ C_FourArco
Xyl group, one benzyloxy group, one C₁~ C_FourAl
A quinthio group, one to three chlorine atoms, a fluorine atom or
Is a bromine atom, one cyano group, one di (C₁~ C_FourAl
Kill) amino group or one 5- or 6-membered heterocyclic group
The heterocyclic group has 1 to 3 oxygen atoms, sulfur atoms or nitrogen atoms.
Contains a chlorine atom, a fluorine atom, a bromine atom and
C₁~ C_FourAn alkyl group (where the alkyl group is
Be replaced by chlorine, fluorine or bromine
No. 1) or 2 substituents selected from the group consisting of
May be replaced. May be replaced by｝. 》, C_Three
~ C₇Cycloalkyl group, C_Three~ C_FiveAlkenyl groups (such
An alkenyl group has 1 to 3 chlorine atoms, fluorine atoms or
May be replaced by a bromine atom. ), C_Three~ C_FiveArchi
Phenyl group, phenyl group (the phenyl group is a chlorine atom,
Nitrogen atom, bromine atom and C₁~ C_FourGroup consisting of alkyl groups
Substituted with 1 to 3 substituents selected from
No. 5) or 6-membered heterocyclic group {the heterocyclic group is 1
Containing 3 to 3 oxygen, sulfur or nitrogen atoms,
One C₁~ C_FourAlkyl group (the alkyl group is 1 to
Replaced by three chlorine, fluorine or bromine atoms
May be. ). ｝, C_Two~ C₈Al
A kill carbonyl group (the alkylcarbonyl group is
Up to three chlorine, fluorine or bromine atoms, one
C₁~ C_FourBy an alkoxy group or one phenoxy group
It may be replaced. ), Benzoyl group (the benzoyl group
Is a chlorine atom, a fluorine atom, a bromine atom and C₁~ C_FourAl
1 to 3 substituents selected from the group consisting of
May be replaced. ), C_Two~ C_FiveAlkoxycarbonyl
Group, di (C₁~ C_FourAlkyl) carbamoyl group, C₁~ C_Four
An alkylsulfonyl group or a phenylsulfonyl group (the
Phenylsulfonyl group is chlorine atom, fluorine atom, bromine
Atom and C₁~ C_Four1 selected from the group consisting of alkyl groups
It may be substituted with up to 3 substituents. ) And R
^TwoAnd R^ThreeAre the same or different and C₁~ C_FourAlkyl group
{The alkyl group has one C_Three~ C₇Cycloalkyl
Group, one phenyl group (the phenyl group is a chlorine atom,
Fluorine atom, bromine atom, C₁~ C_FourAlkyl group and C₁~
C_Four1 to 3 members selected from the group consisting of alkoxy groups
It may be substituted by a substituent. ) One or two C₁~
C_FourAn alkoxy group, one (C₁~ C_FourAlkoxy) C₁~
C_FourAlkoxy group, 1 to 5 chlorine atoms, fluorine atoms
Or a bromine atom or one 5- or 6-membered heterocyclic group
(The heterocyclic group has 1 to 3 oxygen atoms, sulfur atoms or
Contains a nitrogen atom. ). ｝,
C_Three~ C₇Cycloalkyl group, C_Three~ C_FiveAlkenyl group (this
The alkenyl group has 1 to 3 chlorine atoms, fluorine atoms
Or it may be substituted by a bromine atom. ), C_Three~ C_FiveAl
Quinyl group, phenyl group (the phenyl group is a chlorine atom,
Fluorine atom, bromine atom, C₁~ C_FourAlkyl group and C ₁~
C_Four1 to 3 members selected from the group consisting of alkoxy groups
It may be substituted by a substituent. ) Or 5 or 6 members
A heterocyclic group ｛the heterocyclic group has 1 to 3 oxygen atoms,
Atom or nitrogen atom, chlorine atom, fluorine atom, odor
Elementary atom and C₁~ C_FourAlkyl group (the alkyl group is 1
From 3 to 3 chlorine, fluorine or bromine atoms
May be replaced. )) Or one or two selected from the group consisting of
It may be substituted by a substituent. Represents｝, or R^TwoPassing
And R^ThreeTogether with the carbon atom to which they are attached
4 to 7 membered cycloalkane, cycloalkene
Or 1 to 3 cycloalkanediene rings
C₁~ C_FourAlkyl group, one C₁~ C_FourAn alkoxy group,
One (C₁~ C_FourAlkoxy) C₁~ C_FourAn alkoxy group,
One di (C₁~ C_FourAlkyl) amino group, one methyle
Dioxy group, one ethylene dioxy group, one tri
A methylenedioxy group or one N- (C₁~ C_FourAlkoki
B) may be substituted by an imino group,
Oxygen atom, sulfur atom or formula NR^6aA group represented by the formula (wherein
R^6aIs C₁~ C_FourRepresents an alkyl group. Interrupted by
May be. ｝ And R^FiveBut C₁~ C_FourWith an alkyl group
Yes, A is C₁~ C_FourAn alkyl group (the alkyl group is
From 1 to 5 chlorine, fluorine or bromine atoms
It may be replaced. ), Chlorine atom, fluorine atom, bromine atom
Child, C₁~ C_FourAn alkoxy group (the alkoxy group is
Replaced by up to three chlorine, fluorine or bromine atoms
May be. ), C₁~ C_FourAlkylthio group, C₁~ C_FourA
Alkylsulfonyl group, phenyl group (the phenyl group is
Chlorine atom, fluorine atom, bromine atom and C₁~ C_FourAlkyl
With one to three substituents selected from the group consisting of
May be replaced. ) A 5- or 6-membered heterocyclic group
The ring group has 1 to 3 oxygen, sulfur or nitrogen atoms
Containing a chlorine atom, a fluorine atom, a bromine atom and C₁~
C_Four1 or 2 positions selected from the group consisting of alkyl groups
It may be substituted by a substituent. ), Cyano, nitro,
An amino group or a phenoxy group (the phenoxy group is chlorine
Atom, fluorine atom, bromine atom and C₁~ C_FourAlkyl group
Substituted with one to three substituents selected from the group consisting of
May be. And n is 1, 2, 3, 4 or 5.
X is an oxygen atom, a sulfur atom, a sulfinyl group or a sulfur
A compound that is a rufonyl group, more preferably (b ′)
Is R¹Is a hydrogen atom, C₁~ C_ThreeAlkyl group ｛Al
The kill group is one C_Three~ C₆A cycloalkyl group, one
Enyl group, one or two C₁~ C_ThreeAn alkoxy group
The alkoxy group is substituted with one to three chlorine or fluorine atoms.
More may be substituted. ), One (C₁~ C_ThreeAlkoki
C) C₁~ C_ThreeAn alkoxy group, one benzyloxy group,
One C₁~ C_ThreeAlkylthio group, 1 to 3 chlorine atoms
Or a fluorine atom, one cyano group or one 5 or less
Or a 6-membered heterocyclic group (the heterocyclic group is one or two oxygen atoms
Contains atoms or nitrogen atoms. )
No. ｝, C_Three~ C₆Cycloalkyl group, C_Three~ C_FourAlkene
(The alkenyl group is one or two chlorine atoms or
It may be substituted by a fluorine atom. ), C_Three~ C_FourArchi
A phenyl group, a 5- or 6-membered heterocyclic group (the
The ring group contains one or two oxygen or nitrogen atoms
You. ), C_Two~ C₆Alkylcarbonyl group, benzoyl
Group, C_Two~ C_FourAn alkoxycarbonyl group, di (C₁~ C_ThreeA
Alkyl) carbamoyl group, C₁~ C_ThreeAlkylsulfonyl
Or a phenylsulfonyl group,^TwoAnd R^ThreeBut the same
One or different, C₁~ C_ThreeAlkyl group ｛The alkyl group
Is one C_Three~ C₆Cycloalkyl group, one phenyl
Group (the phenyl group is a chlorine atom, a fluorine atom,₁~
C_ThreeAlkyl group and C₁~ C_ThreeGroup consisting of alkoxy groups
Substituted by one or two substituents selected from
No. ) One or two C₁~ C_ThreeAn alkoxy group, one
(C₁~ C_ThreeAlkoxy) C₁~ C_ThreeAlkoxy group, 1 to
3 chlorine or fluorine atoms or 1 5
Is a 6-membered heterocyclic group (the heterocyclic group is one or two oxygen atoms)
Contains a nitrogen atom or a nitrogen atom. )
No. ｝, C_Three~ C₆Cycloalkyl group, C_Three~ C_FourAlkene
Group, C_Three~ C_FourAlkynyl group, phenyl group (the phenyl
A 1 or 2 C₁~ C_ThreeSubstituted by alkoxy group
May be. ) Or a 5- or 6-membered heterocyclic group
Ring groups contain one or two oxygen or nitrogen atoms
You. ) Or R^TwoAnd R^ThreeAre they combined
Together with the carbon atoms that are present
Lucane, cycloalkene or cycloalkanediene
Ring—the ring has one or two C₁~ C_ThreeOne alkyl group
C₁~ C_ThreeAn alkoxy group, one (C₁~ C_ThreeAlkoki
C) C₁~ C_ThreeAn alkoxy group, one di (C₁~ C_ThreeArchi
L) an amino group, one ethylenedioxy group, one tri
A methylenedioxy group or one N- (C₁~ C_ThreeAlkoki
B) may be substituted by an imino group,
Oxygen atom, sulfur atom or formula NR^6bA group represented by the formula (wherein
R^6bIs C₁~ C_ThreeRepresents an alkyl group. Interrupted by
May be. ｝ And R^FiveBut C₁~ C_ThreeWith an alkyl group
Yes, A is C₁~ C_ThreeAn alkyl group (the alkyl group is
Substituted by 1 to 3 chlorine or fluorine atoms
Good. ), Chlorine atom, fluorine atom, bromine atom, C₁~ C_Three
Alkoxy group, C₁~ C_ThreeAlkylthio group, C₁~ C_ThreeAl
Killsulfonyl group, phenyl group, 5- or 6-membered heterocyclic ring
Group (the heterocyclic group is one or two oxygen atoms or nitrogen atoms)
Contains offspring. ), Cyano, nitro, amino or
A phenoxy group, wherein n is 1, 2, 3, 4 or 5
Wherein X is an oxygen atom or a sulfur atom,
(C ') Even more preferably, R¹But C₁~ C_TwoAlkyl
Group—the alkyl group has one C₁~ C_TwoAn alkoxy group,
One (C₁~ C_TwoAlkoxy) C₁~ C_TwoAlkoxy group or
Is one C₁~ C_TwoBe substituted by an alkylthio group
No. ｝ And R^TwoAnd R^ThreeAre the same or different and C₁
~ C_TwoRepresents an alkyl group, or R^TwoAnd R^ThreeAre those
Together with the carbon atom to which it is attached
Ring—the cyclohexane ring contains one or two C₁~ C_Two
Alkyl group, one C₁~ C_TwoAn alkoxy group, one (C
₁~ C_TwoAlkoxy) C₁~ C_TwoAlkoxy group, one ethyl
Rangeoxy group, one trimethylenedioxy group or 1
N- (C₁~ C_TwoSubstituted by an (alkoxy) imino group
May be. ｝ And R^FiveBut C₁~ C_TwoAn alkyl group
A is a methyl group or a chlorine atom, and n is 2 or
3, wherein X is an oxygen atom or a sulfur atom
And (d ') particularly preferably R¹But C₁~ C_TwoArchi
Group (the alkyl group is one C₁~ C_TwoAlkoxy group
May be replaced by ) And R^TwoAnd R^ThreeBut
Represents a methyl group, or R^TwoAnd R^ThreeIs that they
Together with the joining carbon atom to form a cyclohexane ring
｛The cyclohexane ring has one C₁~ C_TwoAlkoxy
Group, ethylenedioxy group, trimethylenedioxy group or
N- (C₁~ C_TwoSubstituted by an (alkoxy) imino group
Good. ｝ And R^FiveIs a methyl group, and A is methyl
And n is 2 or 3, and X is an oxygen atom or
Is a compound that is a sulfur atom.

Compound (III) of the present invention is preferably (a ″)
Suitably, R¹Is a hydrogen atom, C₁~ C_FourAlkyl group <
An alkyl group has one C_Three~ C₇Cycloalkyl group, 1
Phenyl group (the phenyl group is a chlorine atom, a fluorine atom
Child, bromine atom and C₁~ C_FourSelect from the group consisting of alkyl groups
It may be substituted by 1 to 3 substituents. ),
One or two C₁~ C_FourAn alkoxy group (the alkoxy group
Represents 1 to 5 chlorine, fluorine or bromine atoms
More may be substituted. ) One C_Three~ C_FiveAlkenylo
Xyl group, one (C₁~ C_FourAlkoxy) C₁~ C_FourArco
Xyl group, one benzyloxy group, one C₁~ C_FourAl
A quinthio group, one to three chlorine atoms, a fluorine atom or
Is a bromine atom, one cyano group, one di (C₁~ C_FourAl
Kill) amino group or one 5- or 6-membered heterocyclic group
The heterocyclic group has 1 to 3 oxygen atoms, sulfur atoms or nitrogen atoms.
Contains a chlorine atom, a fluorine atom, a bromine atom and
C₁~ C_FourAn alkyl group (where the alkyl group is
Be replaced by chlorine, fluorine or bromine
No. 1) or 2 substituents selected from the group consisting of
May be replaced. May be replaced by｝. 》, C_Three
~ C₇Cycloalkyl group, C_Three~ C_FiveAlkenyl groups (such
An alkenyl group has 1 to 3 chlorine atoms, fluorine atoms or
May be replaced by a bromine atom. ), C_Three~ C_FiveArchi
Phenyl group, phenyl group (the phenyl group is a chlorine atom,
Nitrogen atom, bromine atom and C₁~ C_FourGroup consisting of alkyl groups
Substituted with 1 to 3 substituents selected from
No. 5) or 6-membered heterocyclic group {the heterocyclic group is 1
Containing 3 to 3 oxygen, sulfur or nitrogen atoms,
One C₁~ C_FourAlkyl group (the alkyl group is 1 to
Replaced by three chlorine, fluorine or bromine atoms
May be. ). ｝, C_Two~ C₈Al
A kill carbonyl group (the alkylcarbonyl group is
Up to three chlorine, fluorine or bromine atoms, one
C₁~ C_FourBy an alkoxy group or one phenoxy group
It may be replaced. ), Benzoyl group (the benzoyl group
Is a chlorine atom, a fluorine atom, a bromine atom and C ₁~ C_FourAl
1 to 3 substituents selected from the group consisting of
May be replaced. ), C_Two~ C_FiveAlkoxycarbonyl
Group, di (C₁~ C_FourAlkyl) carbamoyl group, C₁~ C_Four
An alkylsulfonyl group or a phenylsulfonyl group (the
Phenylsulfonyl group is chlorine atom, fluorine atom, bromine
Atom and C₁~ C_Four1 selected from the group consisting of alkyl groups
It may be substituted with up to 3 substituents. ) And R
^TwoAnd R^ThreeAre the same or different and C₁~ C_FourAlkyl group
{The alkyl group has one C_Three~ C₇Cycloalkyl
Group, one phenyl group (the phenyl group is a chlorine atom,
Fluorine atom, bromine atom, C₁~ C_FourAlkyl group and C₁~
C_Four1 to 3 members selected from the group consisting of alkoxy groups
It may be substituted by a substituent. ) One or two C₁~
C_FourAn alkoxy group, one (C₁~ C_FourAlkoxy) C₁~
C_FourAlkoxy group, 1 to 5 chlorine atoms, fluorine atoms
Or a bromine atom or one 5- or 6-membered heterocyclic group
(The heterocyclic group has 1 to 3 oxygen atoms, sulfur atoms or
Contains a nitrogen atom. ). ｝,
C_Three~ C₇Cycloalkyl group, C_Three~ C_FiveAlkenyl group (this
The alkenyl group has 1 to 3 chlorine atoms, fluorine atoms
Or it may be substituted by a bromine atom. ), C_Three~ C_FiveAl
Quinyl group, phenyl group (the phenyl group is a chlorine atom,
Fluorine atom, bromine atom, C₁~ C_FourAlkyl group and C ₁~
C_Four1 to 3 members selected from the group consisting of alkoxy groups
It may be substituted by a substituent. ) Or 5 or 6 members
A heterocyclic group ｛the heterocyclic group has 1 to 3 oxygen atoms,
Atom or nitrogen atom, chlorine atom, fluorine atom, odor
Elementary atom and C₁~ C_FourAlkyl group (the alkyl group is 1
From 3 to 3 chlorine, fluorine or bromine atoms
May be replaced. )) Or one or two selected from the group consisting of
It may be substituted by a substituent. Represents｝, or R^TwoPassing
And R^ThreeTogether with the carbon atom to which they are attached
4 to 7 membered cycloalkane, cycloalkene
Or 1 to 3 cycloalkanediene rings
C₁~ C_FourAlkyl group, one C₁~ C_FourAn alkoxy group,
One (C₁~ C_FourAlkoxy) C₁~ C_FourAn alkoxy group,
One di (C₁~ C_FourAlkyl) amino group, one methyle
Dioxy group, one ethylene dioxy group, one tri
A methylenedioxy group or one N- (C₁~ C_FourAlkoki
B) may be substituted by an imino group,
Oxygen atom, sulfur atom or formula NR^6aA group represented by the formula (wherein
R^6aIs C₁~ C_FourRepresents an alkyl group. Interrupted by
May be. ｝ And R^FiveBut C₁~ C_FourWith an alkyl group
Yes, A is C₁~ C_FourAn alkyl group (the alkyl group is
From 1 to 5 chlorine, fluorine or bromine atoms
It may be replaced. ), Chlorine atom, fluorine atom, bromine atom
Child, C₁~ C_FourAn alkoxy group (the alkoxy group is
Replaced by up to three chlorine, fluorine or bromine atoms
May be. ), C₁~ C_FourAlkylthio group, C₁~ C_FourA
Alkylsulfonyl group, phenyl group (the phenyl group is
Chlorine atom, fluorine atom, bromine atom and C₁~ C_FourAlkyl
With one to three substituents selected from the group consisting of
May be replaced. ) A 5- or 6-membered heterocyclic group
The ring group has 1 to 3 oxygen, sulfur or nitrogen atoms
Containing a chlorine atom, a fluorine atom, a bromine atom and C₁~
C_Four1 or 2 positions selected from the group consisting of alkyl groups
It may be substituted by a substituent. ), Cyano, nitro,
An amino group or a phenoxy group (the phenoxy group is chlorine
Atom, fluorine atom, bromine atom and C₁~ C_FourAlkyl group
Substituted with one to three substituents selected from the group consisting of
May be. And n is 1, 2, 3, 4 or 5.
X is an oxygen atom, a sulfur atom, a sulfinyl group or a sulfur
A compound that is a rufonyl group, more preferably (b ″)
Is R¹Is a hydrogen atom, C₁~ C_ThreeAlkyl group ｛Al
The kill group is one C_Three~ C₆A cycloalkyl group, one
Enyl group, one or two C₁~ C_ThreeAn alkoxy group
The alkoxy group is substituted with one to three chlorine or fluorine atoms.
More may be substituted. ), One (C₁~ C_ThreeAlkoki
C) C₁~ C_ThreeAn alkoxy group, one benzyloxy group,
One C₁~ C_ThreeAlkylthio group, 1 to 3 chlorine atoms
Or a fluorine atom, one cyano group or one 5 or less
Or a 6-membered heterocyclic group (the heterocyclic group is one or two oxygen atoms
Contains atoms or nitrogen atoms. )
No. ｝, C_Three~ C₆Cycloalkyl group, C_Three~ C_FourAlkene
(The alkenyl group is one or two chlorine atoms or
It may be substituted by a fluorine atom. ), C_Three~ C_FourArchi
A phenyl group, a 5- or 6-membered heterocyclic group (the
The ring group contains one or two oxygen or nitrogen atoms
You. ), C_Two~ C₆Alkylcarbonyl group, benzoyl
Group, C_Two~ C_FourAn alkoxycarbonyl group, di (C₁~ C_ThreeA
Alkyl) carbamoyl group, C₁~ C_ThreeAlkylsulfonyl
Or a phenylsulfonyl group,^TwoAnd R^ThreeBut the same
One or different, C₁~ C_ThreeAlkyl group ｛The alkyl group
Is one C_Three~ C₆Cycloalkyl group, one phenyl
Group (the phenyl group is a chlorine atom, a fluorine atom,₁~
C_ThreeAlkyl group and C₁~ C_ThreeGroup consisting of alkoxy groups
Substituted by one or two substituents selected from
No. ) One or two C₁~ C_ThreeAn alkoxy group, one
(C₁~ C_ThreeAlkoxy) C₁~ C_ThreeAlkoxy group, 1 to
3 chlorine or fluorine atoms or 1 5
Is a 6-membered heterocyclic group (the heterocyclic group is one or two oxygen atoms)
Contains a nitrogen atom or a nitrogen atom. )
No. ｝, C_Three~ C₆Cycloalkyl group, C_Three~ C_FourAlkene
Group, C_Three~ C_FourAlkynyl group, phenyl group (the phenyl
A 1 or 2 C₁~ C_ThreeSubstituted by alkoxy group
May be. ) Or a 5- or 6-membered heterocyclic group
Ring groups contain one or two oxygen or nitrogen atoms
You. ) Or R^TwoAnd R^ThreeAre they combined
Together with the carbon atoms that are present
Lucane, cycloalkene or cycloalkanediene
Ring—the ring has one or two C₁~ C_ThreeOne alkyl group
C₁~ C_ThreeAn alkoxy group, one (C₁~ C_ThreeAlkoki
C) C₁~ C_ThreeAn alkoxy group, one di (C₁~ C_ThreeArchi
L) an amino group, one ethylenedioxy group, one tri
A methylenedioxy group or one N- (C₁~ C_ThreeAlkoki
B) may be substituted by an imino group,
Oxygen atom, sulfur atom or formula NR^6bA group represented by the formula (wherein
R^6bIs C₁~ C_ThreeRepresents an alkyl group. Interrupted by
May be. ｝ And R^FiveBut C₁~ C_ThreeWith an alkyl group
Yes, A is C₁~ C_ThreeAn alkyl group (the alkyl group is
Substituted by 1 to 3 chlorine or fluorine atoms
Good. ), Chlorine atom, fluorine atom, bromine atom, C₁~ C_Three
Alkoxy group, C₁~ C_ThreeAlkylthio group, C₁~ C_ThreeAl
Killsulfonyl group, phenyl group, 5- or 6-membered heterocyclic ring
Group (the heterocyclic group is one or two oxygen atoms or nitrogen atoms)
Contains offspring. ), Cyano, nitro, amino or
A phenoxy group, wherein n is 1, 2, 3, 4 or 5
Wherein X is an oxygen atom or a sulfur atom,
(C ″) Even more preferably, R¹But C₁~ C_TwoAlkyl
Group—the alkyl group has one C₁~ C_TwoAn alkoxy group,
One (C₁~ C_TwoAlkoxy) C₁~ C_TwoAlkoxy group or
Is one C₁~ C_TwoBe substituted by an alkylthio group
No. ｝ And R^TwoAnd R^ThreeAre the same or different and C₁
~ C_TwoRepresents an alkyl group, or R^TwoAnd R^ThreeAre those
Together with the carbon atom to which it is attached
Ring—the cyclohexane ring contains one or two C₁~ C_Two
Alkyl group, one C₁~ C_TwoAn alkoxy group, one (C
₁~ C_TwoAlkoxy) C₁~ C_TwoAlkoxy group, one ethyl
Rangeoxy group, one trimethylenedioxy group or 1
N- (C₁~ C_TwoSubstituted by an (alkoxy) imino group
May be. ｝ And R^FiveBut C₁~ C_TwoAn alkyl group
A is a methyl group or a chlorine atom, and n is 2 or
3, wherein X is an oxygen atom or a sulfur atom
And (d ″) particularly preferably R¹But C₁~ C_TwoArchi
Group (the alkyl group is one C₁~ C_TwoAlkoxy group
May be replaced by ) And R^TwoAnd R^ThreeBut
Represents a methyl group, or R^TwoAnd R^ThreeIs that they
Together with the joining carbon atom to form a cyclohexane ring
｛The cyclohexane ring has one C₁~ C_TwoAlkoxy
Group, ethylenedioxy group, trimethylenedioxy group or
N- (C₁~ C_TwoSubstituted by an (alkoxy) imino group
Good. ｝ And R^FiveIs a methyl group, and A is methyl
And n is 2 or 3, and X is an oxygen atom or
Is a compound that is a sulfur atom.

The representative compounds of the present invention are shown in the following Tables 1 to 12, but the present invention is not limited to these compounds.

Hereinafter, “Me” represents a methyl group, “Et” represents an ethyl group, “Pr” represents a propyl group, “iPr” represents an isopropyl group, “cPr” represents a cyclopropyl group, and “cPr (1 -Me, 2,
2-Cl ₂ ) ”is a 1-methyl-2,2-dichlorocyclopropyl group,“ Bu ”is a butyl group,“ tBu ”is a tert-butyl group,“ iBu ”is an isobutyl group, and“ sBu ” Is a sec-butyl group, `` cBu '' is a cyclobutyl group, `` cPent '' is a cyclopentyl group, `` cHex '' is a cyclohexyl group, `` 2,6-Cl
_2, the 4-CF ₃ "is 2,6-dichloro-4-trifluoromethyl group," Ac "means acetyl group," Ph "a phenyl group," 2-Cl-Ph "2-chlorophenyl group , "Tol" is a tolyl group, "2-Thf" is a 2-tetrahydrofuranyl group, "2-Diox" is a 2-dioxolanyl group, and "3-Pyr"
Is a 3-pyridyl group, `` 5-Pym '' is a 5-pyrimidinyl group, `` 2-SMe, 4-CF ₃ -5-Pym '' is a 2-methylthio-4-trifluoromethyl-5-pyrimidinyl group, "4-Pyza"
Is a 4-pyrazolyl group, "2-Thiophene" is a 2-thienyl group, "5-Me-6-Chr" is a 5-methylchroman-6-yl group, and "N-Mor" is an N-morpholinyl group To `` 5-
Q ¹ ”represents a benzo [1,3] dioxol-5-yl group,
“5-Q ² ” represents a [1,2,3] thiadiazol-5-yl group, “3-Q ³ ” represents an oxetan-3-yl group, and “2-Q ⁴ ” represents 1,3-dioxane-yl. A 2-yl group, “NH ₄ ⁺ ” is a group OR ⁴
There formula O ^- that the ammonium salt represented by NH ₄ ^+, respectively.

[0089]

[Table 1]

[0090]

Embedded image 化合物 Compound number R ¹ R ² R ³ R ⁴ ──── ──────────────────────────────── 1-1 H Me Me H 1-2 H Me Me Ac 1-3 H Me Me COEt 1-4 H Me Me COPh 1-5 H Me Me COCH ₂ tBu 1-6 H Me Me COtBu 1-7 H Me Me COC (Me) ₂ Et 1-8 H Me Me CO ₂ Me 1-9 H Me Me C (S) SEt 1-10 H Me Me C (S) SPr 1-11 H Me Me CH ₂ OMe 1-12 H Me Me CH ₂ OPh 1-13 Me Me Me H 1-14 Me Me Me Ac 1-15 Me Me Me COEt 1-16 Me Me Me COPr 1-17 Me Me Me COiPr 1-18 Me Me Me COBu 1-19 Me Me Me COtBu 1-20 Me Me Me COcHex 1-21 Me Me Me COPh 1-22 Me Me Me CO (2-Cl-Ph) 1-23 Me Me Me COCH = CH ₂ 1-24 Me Me Me COC (Me) = CH ₂ 1-25 Me Me Me COCH ₂ OMe 1-26 Me Me Me COCH ₂ OPh 1-27 Me Me Me COCH ₂ tBu 1-28 Me Me Me CO ₂ Me 1-29 Me Me Me CO ₂ Et 1-30 Me Me Me CO ₂ Pr 1-31 Me Me Me CO ₂ iPr 1-32 Me Me Me CO ₂ Bu 1-33 Me Me Me CO ₂ iBu 1-34 Me Me Me CO ₂ tBu 1-35 Me Me Me CO ₂ cPent 1-36 Me Me M e CO ₂ cHex 1-37 Me Me Me CO ₂ CH ₂ CH = CH ₂ 1-38 Me Me Me CO ₂ CH ₂ tBu 1-39 Me Me Me CO ₂ CH ₂ (2-Thf) 1-40 Me Me Me CO ₂ CH ₂ C (Me) ₂ CH ₂ Cl 1-41 Me Me Me CO ₂ CH (Me) iPr 1-42 Me Me Me C (O) SMe 1-43 Me Me Me C (O) SEt 1-44 Me Me Me C (O) S-tBu 1-45 Me Me Me C (O) SPh 1-46 Me Me Me C (S) OMe 1-47 Me Me Me C (S) OEt 1-48 Me Me Me C (S) OtBu 1-49 Me Me Me C (S) OPh 1-50 Me Me Me C (S) SMe 1-51 Me Me Me C (S) SEt 1-52 Me Me Me C (S) SPr 1- 53 Me Me Me C (S) S-iPr 1-54 Me Me Me C (S) SBu 1-55 Me Me Me C (S) S-tBu 1-56 Me Me Me C (S) SCH ₂ tBu 1- 57 Me Me Me C (S) SPh 1-58 Me Me Me Me 1-59 Me Me Me CH ₂ OMe 1-60 Me Me Me CH ₂ OPh 1-61 Me Me Me CH ₂ Ph 1-62 Me Me Me SO ₂ Me 1-63 Me Me Me SO ₂ Et 1-64 Me Me Me SO ₂ Ph 1-65 Me Me Me SO ₂ (4-Me-Ph) 1-66 Me Me Me P (S) (OMe) ₂ 1 -67 Me Me Me P (S) (OEt) 2 1-68 Me Me Me Na 1-69 Me Me Me K 1-70 Me Me Me NH 4 + 1-71 Et Me Me H 1-72 Et Me Me COtBu 1-73 Et Me Me COCH ₂ tBu 1-74 Et Me Me C (S) SEt 1-75 Pr Me Me H 1-76 Pr Me Me COtBu 1-77 Pr Me Me COCH ₂ tBu 1-78 Pr Me Me C (S) SEt 1-79 iPr M e Me H 1-80 iPr Me Me COtBu 1-81 iPr Me Me COCH ₂ tBu 1-82 iPr Me Me C (S) SEt 1-83 CH ₂ CH = CH ₂ Me Me H 1-84 CH ₂ CH = CH ₂ Me Me COtBu 1-85 CH ₂ CH = CH ₂ Me Me COCH ₂ tBu 1-86 CH ₂ CH = CH ₂ Me Me C (S) SEt 1-87 CH ₂ C≡CH Me Me H 1-88 CH ₂ C≡CH Me Me COtBu 1-89 CH ₂ C≡CH Me Me COCH ₂ tBu 1-90 CH ₂ C≡CH Me Me C (S) SEt 1-91 CH ₂ cHex Me Me H 1-92 CH ₂ cHex Me Me COtBu 1-93 CH ₂ cHex Me Me COCH ₂ tBu 1-94 CH ₂ cHex Me Me C (S) SEt 1-95 CH ₂ Ph Me Me H 1-96 CH ₂ Ph Me Me COtBu 1-97 CH ₂ Ph Me Me COCH ₂ tBu 1-98 CH ₂ Ph Me Me C (S) SEt 1-99 CH ₂ OMe Me Me H 1-100 CH ₂ OMe Me Me Ac 1-101 CH ₂ OMe Me Me COEt 1-102 CH ₂ OMe Me Me COPr 1-103 CH ₂ OMe Me Me COiPr 1-104 CH ₂ OMe Me Me COBu 1-105 CH ₂ OMe Me Me COtBu 1-106 CH ₂ OMe Me Me COcHex 1-107 CH ₂ OMe Me Me COPh 1 -108 CH ₂ OMe Me Me COCH = CH ₂ 1-109 CH ₂ OMe Me Me COCH ₂ OMe 1-110 CH ₂ OMe Me Me COCH ₂ OPh 1-111 CH ₂ OMe Me Me COCH ₂ tBu 1-112 CH ₂ OMe Me Me COC (Me) ₂ CH ₂ Cl 1-113 CH ₂ OMe Me Me CO ₂ Me 1-114 CH ₂ OMe Me Me CO ₂ Et 1-115 CH ₂ OMe Me Me CO ₂ Pr 1-116 CH ₂ OMe Me Me CO ₂ iPr 1-117 CH ₂ OMe Me Me CO ₂ Bu 1-118 CH ₂ OMe Me Me CO ₂ iBu 1-119 CH ₂ OMe Me Me CO ₂ tBu 1-120 CH ₂ OMe Me Me CO ₂ cPent 1-121 CH ₂ OMe Me Me CO ₂ cHex 1-122 CH ₂ OMe Me Me CO ₂ CH ₂ CH = CH ₂ 1-123 CH ₂ OMe Me Me CO ₂ CH ₂ tBu 1-124 CH ₂ OMe Me Me CO ₂ CH ₂ (2-Thf) 1-125 CH ₂ OMe Me Me CO ₂ CH ₂ C (Me) ₂ CH ₂ Cl 1-126 CH ₂ OMe Me Me CO ₂ CH ( Me) iPr 1-127 CH ₂ OMe Me Me C (S) SMe 1-128 CH ₂ OMe Me Me C (S) SEt 1-129 CH ₂ OMe Me Me C (S) SPr 1-130 CH ₂ OMe Me Me C (S) S-iPr 1-131 CH ₂ OMe Me Me C (S) SBu 1-132 CH ₂ OMe Me Me C (S) S-tBu 1-133 CH ₂ OMe Me Me C (S) SCH ₂ tBu 1-134 CH ₂ OMe Me Me C (S) SPh 1-135 CH ₂ OEt Me Me H 1-136 CH ₂ OEt Me Me COtBu 1-137 CH ₂ OEt Me Me COCH ₂ tBu 1-138 CH ₂ OEt Me Me C (S) SEt 1-139 CH ₂ CH ₂ OMe Me Me H 1-140 CH ₂ CH ₂ OMe Me Me COtBu 1-141 CH ₂ CH ₂ OMe Me Me COCH ₂ tBu 1-142 CH ₂ CH ₂ OMe Me Me C (S) SEt 1-143 CH ₂ O (CH ₂ ) ₂ OMe Me Me H 1-144 CH ₂ O (CH ₂ ) ₂ OMe Me Me COtBu 1-145 CH ₂ O (CH ₂ ) ₂ OMe Me Me COCH ₂ tBu 1-146 CH ₂ O (CH ₂ ) ₂ OMe Me Me C (S) SEt 1-147 CH ₂ SMe Me Me H 1-148 CH ₂ SMe Me Me COtBu 1-149 CH ₂ SMe Me Me COCH ₂ tBu 1-150 CH ₂ SMe Me Me C (S) SEt 1-151 CH ₂ CH (OMe) ₂ Me Me H 1-152 CH ₂ CH (OMe) ₂ Me Me COtBu 1-153 CH ₂ CH (OMe) ₂ Me Me COCH ₂ tBu 1 -154 CH ₂ CH (OMe) ₂ Me Me C (S) SEt 1-155 CH ₂ (2-Diox) Me Me H 1-156 CH ₂ (2-Diox) Me Me COtBu 1-157 CH ₂ (2- Diox) Me Me COCH ₂ tBu 1-158 CH ₂ (2-Diox) Me Me C (S) SEt 1-159 CH ₂ (2-Thf) Me Me H 1-160 CH ₂ (2-Thf) Me Me COtBu 1-161 CH ₂ (2-Thf) Me Me COCH ₂ tBu 1-162 CH ₂ (2-Thf) Me Me C (S) SEt 1-163 CH ₂ (3-Pyr) Me Me H 1-164 CH ₂ (3-Pyr) Me Me COtBu 1-165 CH ₂ (3-Pyr) Me Me COCH ₂ tBu 1-166 CH ₂ (3-Pyr) Me Me C (S) SEt 1-167 CH ₂ CN Me Me H 1 -168 CH ₂ CN Me Me COtBu 1-169 CH ₂ CN Me Me COCH ₂ tBu 1-170 CH ₂ CN Me Me C (S) SEt 1-171 CH ₂ OCH ₂ Ph Me Me H 1-172 CH ₂ OCH ₂ Ph Me Me COtBu 1-173 CH ₂ OCH ₂ Ph Me Me COCH ₂ tBu 1-174 CH ₂ OCH ₂ Ph Me Me C (S) SEt 1-175 CH ₂ Cl Me Me H 1-176 CH ₂ Cl Me Me COtBu 1-177 CH ₂ Cl Me Me COCH ₂ tBu 1-178 CH ₂ Cl Me Me C (S) SEt 1-179 CH ₂ OCH ₂ CF ₃ Me Me H 1-180 CH ₂ OCH ₂ CF ₃ Me Me COtBu 1-181 CH ₂ OCH ₂ CF ₃ Me Me COCH ₂ tBu 1-182 CH ₂ OCH ₂ CF ₃ Me Me C (S) SEt 1-183 CH ₂ OiPr Me Me H 1-184 CH ₂ OiPr Me Me COtBu 1-185 CH ₂ OiPr Me Me COCH ₂ tBu 1-186 CH ₂ OiPr Me Me C (S ) SEt 1-187 CH ₂ OCH ₂ CH = CH ₂ Me Me H 1-188 CH ₂ OCH ₂ CH = CH ₂ Me Me COtBu 1-189 CH ₂ OCH ₂ CH = CH ₂ Me Me COCH ₂ tBu 1-190 CH ₂ OCH ₂ CH = CH ₂ Me Me C (S) SEt 1-191 CH ₂ CH = CHCl Me Me H 1-192 CH ₂ CH = CHCl Me Me COtBu 1-193 CH ₂ CH = CHCl Me Me COCH ₂ tBu 1 -194 CH ₂ CH = CHCl Me Me C (S) SEt 1-195 CH ₂ NMe ₂ Me Me H 1-196 CH ₂ NMe ₂ Me Me COtBu 1-197 CH ₂ NMe ₂ Me Me COCH ₂ tBu 1-198 CH ₂ NMe ₂ Me Me C (S) SEt 1-199 Ph Me Me H 1-200 Ph Me Me COtBu 1-201 Ph Me Me COCH ₂ tBu 1-202 Ph Me Me C (S) SEt 1-203 2-Pyr Me Me H 1-204 2-Pyr Me Me COtBu 1-205 2-Pyr Me Me COCH ₂ tBu 1-206 2-Pyr Me Me C (S) SEt 1-207 4-CF ₃ -2-Pyr Me Me H 1-208 4-CF ₃ -2-Pyr Me Me COtBu 1-209 4-CF ₃ -2-Pyr Me Me COCH ₂ tBu 1-210 4-CF ₃ -2-Pyr Me Me C (S) SEt 1- 211 2-Thiophene Me Me H 1-212 2-Thiophene Me Me COtBu 1-213 2-Thiophene Me Me COCH ₂ tBu 1-214 2-Thiophene Me Me C (S) SEt 1-215 Ac Me Me COtBu 1-216 Ac Me Me COCH ₂ tBu 1-217 COtBu Me Me COtBu 1-218 COtBu Me Me COCH ₂ tBu 1-219 COPh Me Me COtBu 1-220 COPh Me Me COCH ₂ tBu 1-221 COCH ₂ tBu Me Me COtBu 1-222 COCH ₂ tBu Me Me COCH ₂ tBu 1-223 CO ₂ Me Me Me COtBu 1-224 CO ₂ Me Me Me COCH ₂ tBu 1-225 CONMe ₂ Me Me COtBu 1-226 CONMe ₂ Me Me COCH ₂ tBu 1-227 SO ₂ Me Me Me COtBu 1-228 SO ₂ Me Me Me COCH ₂ tBu 1-229 SO ₂ Tol Me Me COtBu 1-230 SO ₂ Tol Me Me COCH ₂ tBu 1-231 Me Me Et H 1-232 Me Me Et COtBu 1-233 Me Me Et COCH ₂ tBu 1-234 Me Me Et C (S) SEt 1-235 Me Me Pr H 1-236 Me Me Pr COtBu 1-237 Me Me Pr COCH ₂ tBu 1-238 Me Me Pr C (S) SEt 1 -239 Me Me iPr H 1-240 Me Me iPr COtBu 1-241 Me Me iPr COCH ₂ tBu 1-242 Me Me iPr C (S) SEt 1-243 Me Me cPr H 1-244 Me Me cPr COtBu 1-245 Me Me cPr COCH ₂ tBu 1-246 Me Me cPr C (S) SEt 1-247 Me Me CH ₂ CH = CH ₂ H 1-248 Me Me CH ₂ CH = CH ₂ COtBu 1-249 Me Me CH ₂ CH = CH ₂ COCH ₂ tBu 1-25 0 Me Me CH ₂ CH = CH ₂ C (S) SEt 1-251 Me Me Ph H 1-252 Me Me Ph COtBu 1-253 Me Me Ph COCH ₂ tBu 1-254 Me Me Ph C (S) SEt 1- 255 Me Me CF ₃ H 1-256 Me Me CF ₃ COtBu 1-257 Me Me CF ₃ COCH ₂ tBu 1-258 Me Me CF ₃ C (S) SEt 1-259 Me Me CH ₂ Ph H 1-260 Me Me CH ₂ Ph COtBu 1-261 Me Me CH ₂ Ph COCH ₂ tBu 1-262 Me Me CH ₂ Ph C (S) SEt 1-263 Me Me Ph H 1-264 Me Me Ph COtBu 1-265 Me Me Ph COCH ₂ tBu 1-266 Me Me Ph C (S) SEt 1-267 Me Et Et H 1-268 Me Et Et COtBu 1-269 Me Et Et COCH ₂ tBu 1-270 Me Et Et C (S) SEt 1-271 Me -(CH ₂ ) ₅ -H 1-272 Me-(CH ₂ ) ₅ -COtBu 1-273 Me-(CH ₂ ) ₅ -COCH ₂ tBu 1-274 Me-(CH ₂ ) ₅ -C (S) SEt 1-275 Me-(CH ₂ ) ₂ -CH (Me)-(CH ₂ ) ₂ -H 1-276 Me-(CH ₂ ) ₂ -CH (Me)-(CH ₂ ) ₂ -COtBu 1-277 Me -(CH ₂ ) ₂ -CH (Me)-(CH ₂ ) ₂ -COCH ₂ tBu 1-278 Me-(CH ₂ ) ₂ -CH (Me)-(CH ₂ ) ₂ -C (S) SEt 1- 279 Me-(CH ₂ ) ₂ -CH (OMe)-(CH ₂ ) ₂ -H 1-280 Me-(CH ₂ ) ₂ -CH (OMe)-(CH ₂ ) ₂ -COtBu 1-281 Me-( CH ₂ ) ₂ -CH (OMe)-(CH ₂ ) ₂ -COCH ₂ tBu 1-282 Me-(CH ₂ ) ₂ -CH (OMe)-(CH ₂ ) ₂ -C (S) SEt 1-283 Me -(CH ₂ ) ₂ -CH (NMe ₂ )-(CH ₂ ) ₂ -H 1-284 Me-(CH ₂ ) ₂ -CH (NMe ₂ )-(CH ₂ ) ₂ -COtBu 1-285 Me-(CH ₂ ) ₂ -CH (NMe ₂ )-(CH ₂ ) ₂ -COCH ₂ tBu 1-286 Me-(CH ₂ ) ₂ -CH (NMe ₂ )-(CH ₂ ) ₂ -C (S) SEt 1-287 Me-( CH ₂ ) ₂ -O- (CH ₂ ) ₂ -H 1-288 Me-(CH ₂ ) ₂ -O- (CH ₂ ) ₂ -COtBu 1-289 Me-(CH ₂ ) ₂ -O- (CH ₂ ) ₂ -COCH ₂ tBu 1-290 Me-(CH ₂ ) ₂ -O- (CH ₂ ) ₂ -C (S) SEt 1-291 Me-(CH ₂ ) ₂ -S- (CH ₂ ) ₂ -H 1-292 Me-(CH ₂ ) ₂ -S- (CH ₂ ) ₂ -COtBu 1-293 Me-(CH ₂ ) ₂ -S- (CH ₂ ) ₂ -COCH ₂ tBu 1-294 Me-(CH ₂ ) ₂ -S- (CH ₂ ) ₂ -C (S) SEt 1-295 Me-(CH ₂ ) ₂ -NMe- (CH ₂ ) ₂ -H 1-296 Me-(CH ₂ ) ₂ -NMe- ( CH ₂ ) ₂ -COtBu 1-297 Me-(CH ₂ ) ₂ -NMe- (CH ₂ ) ₂ -COCH ₂ tBu 1-298 Me-(CH ₂ ) ₂ -NMe- (CH ₂ ) ₂ -C (S ) SEt 1-299 CH ₂ OMe Me Et H 1-300 CH ₂ OMe Me Et COtBu 1-301 CH ₂ OMe Me Pr H 1-302 CH ₂ OMe Me Pr COtBu 1-303 CH ₂ OMe Me iPr H 1-304 CH ₂ OMe Me iPr COtBu 1-305 CH ₂ OMe Me cPr H 1-306 CH ₂ OMe Me cPr COtBu 1-307 CH ₂ OMe Me Ph H 1-308 CH ₂ OMe Me Ph COtBu 1-309 CH ₂ OMe Me CF ₃ H 1-310 CH ₂ OMe Me CF ₃ C OtBu 1-311 CH ₂ OMe Me CH ₂ Ph H 1-312 CH ₂ OMe Me CH ₂ Ph COtBu 1-313 CH ₂ OMe Me Ph H 1-314 CH ₂ OMe Me Ph COtBu 1-315 CH ₂ OMe Et Et H 1-316 CH ₂ OMe Et Et COtBu 1-317 CH ₂ OMe-(CH ₂ ) ₅ -H 1-318 CH ₂ OMe-(CH ₂ ) ₅ -COtBu 1-319 CH ₂ OMe-(CH ₂ ) _2- CH (Me)-(CH ₂ ) ₂ -H 1-320 CH ₂ OMe-(CH ₂ ) ₂ -CH (Me)-(CH ₂ ) ₂ -COtBu 1-321 CH ₂ OMe-(CH ₂ ) _2- CH (OMe)-(CH ₂ ) ₂ -H 1-322 CH ₂ OMe-(CH ₂ ) ₂ -CH (OMe)-(CH ₂ ) ₂ -COtBu 1-323 CH ₂ OMe-(CH ₂ ) _2- O- (CH ₂ ) ₂ -H 1-324 CH ₂ OMe-(CH ₂ ) ₂ -O- (CH ₂ ) ₂ -COtBu 1-325 CH ₂ OMe-(CH ₂ ) ₂ -S- (CH ₂ ) ₂ -H 1-326 CH ₂ OMe-(CH ₂ ) ₂ -S- (CH ₂ ) ₂ -COtBu 1-327 CH ₂ OMe-(CH ₂ ) ₂ -NMe- (CH ₂ ) ₂ -H 1-328 CH ₂ OMe-(CH ₂ ) ₂ -NMe- (CH ₂ ) ₂ -COtBu 1-329 CH ₂ OEt Me Et H 1-330 CH ₂ OEt Me Et COtBu 1-331 CH ₂ OEt Me Pr H 1-332 CH ₂ OEt Me Pr COtBu 1-333 CH ₂ OEt Me iPr H 1-334 CH ₂ OEt Me iPr COtBu 1-335 CH ₂ OEt Me cPr H 1-336 CH ₂ OEt Me cPr COtBu 1-337 CH ₂ OEt Me Ph H 1-338 CH ₂ OEt Me Ph COtBu 1-339 CH ₂ OEt Me CF ₃ H 1-340 CH ₂ OEt M e CF ₃ COtBu 1-341 CH ₂ OEt Me CH ₂ Ph H 1-342 CH ₂ OEt Me CH ₂ Ph COtBu 1-343 CH ₂ OEt Me Ph H 1-344 CH ₂ OEt Me Ph COtBu 1-345 CH ₂ OEt Et Et H 1-346 CH ₂ OEt Et Et COtBu 1-347 CH ₂ OEt-(CH ₂ ) ₅ -H 1-348 CH ₂ OEt-(CH ₂ ) ₅ -COtBu 1-349 CH ₂ OEt-(CH ₂ ) ₂ -CH (Me)-(CH ₂ ) ₂ -H 1-350 CH ₂ OEt-(CH ₂ ) ₂ -CH (Me)-(CH ₂ ) ₂ -COtBu 1-351 CH ₂ OEt-(CH ₂ ) ₂ -CH (OMe)-(CH ₂ ) ₂ -H 1-352 CH ₂ OEt-(CH ₂ ) ₂ -CH (OMe)-(CH ₂ ) ₂ -COtBu 1-353 CH ₂ OEt-(CH ₂ ) ₂ -O- (CH ₂ ) ₂ -H 1-354 CH ₂ OEt-(CH ₂ ) ₂ -O- (CH ₂ ) ₂ -COtBu 1-355 CH ₂ OEt-(CH ₂ ) ₂ -S- ( CH ₂ ) ₂ -H 1-356 CH ₂ OEt-(CH ₂ ) ₂ -S- (CH ₂ ) ₂ -COtBu 1-357 CH ₂ OEt-(CH ₂ ) ₂ -NMe- (CH ₂ ) ₂ -H 1-358 CH ₂ OEt-(CH ₂ ) ₂ -NMe- (CH ₂ ) ₂ -COtBu 1-359 CH ₂ CH ₂ OMe Me Et H 1-360 CH ₂ CH ₂ OMe Me Et COtBu 1-361 CH ₂ CH ₂ OMe Me Pr H 1-362 CH ₂ CH ₂ OMe Me Pr COtBu 1-363 CH ₂ CH ₂ OMe Me iPr H 1-364 CH ₂ CH ₂ OMe Me iPr COtBu 1-365 CH ₂ CH ₂ OMe Me cPr H 1 -366 CH ₂ CH ₂ OMe Me cPr COtBu 1-367 CH ₂ CH ₂ OMe Me Ph H 1-368 CH ₂ CH ₂ OMe Me Ph COtBu 1-369 CH ₂ CH ₂ OMe Me CF ₃ H 1-370 CH ₂ CH ₂ OMe Me CF ₃ COtBu 1-371 CH ₂ CH ₂ OMe Me CH ₂ Ph H 1-372 CH ₂ CH ₂ OMe Me CH ₂ Ph COtBu 1-373 CH ₂ CH ₂ OMe Me Ph H 1-374 CH ₂ CH ₂ OMe Me Ph COtBu 1-375 CH ₂ CH ₂ OMe Et Et H 1-376 CH ₂ CH ₂ OMe Et Et COtBu 1- 377 CH ₂ CH ₂ OMe-(CH ₂ ) ₅ -H 1-378 CH ₂ CH ₂ OMe-(CH ₂ ) ₅ -COtBu 1-379 CH ₂ CH ₂ OMe-(CH ₂ ) ₂ -CH (Me)- (CH ₂ ) ₂ -H 1-380 CH ₂ CH ₂ OMe-(CH ₂ ) ₂ -CH (Me)-(CH ₂ ) ₂ -COtBu 1-381 CH ₂ CH ₂ OMe-(CH ₂ ) ₂ -CH (OMe)-(CH ₂ ) ₂ -H 1-382 CH ₂ CH ₂ OMe-(CH ₂ ) ₂ -CH (OMe)-(CH ₂ ) ₂ -COtBu 1-383 CH ₂ CH ₂ OMe-(CH ₂ ) ₂ -O- (CH ₂ ) ₂ -H 1-384 CH ₂ CH ₂ OMe-(CH ₂ ) ₂ -O- (CH ₂ ) ₂ -COtBu 1-385 CH ₂ CH ₂ OMe-(CH ₂ ) ₂ -S- (CH ₂ ) ₂ -H 1-386 CH ₂ CH ₂ OMe-(CH ₂ ) ₂ -S- (CH ₂ ) ₂ -COtBu 1-387 CH ₂ CH ₂ OMe-(CH ₂ ) ₂ -NMe -(CH ₂ ) ₂ -H 1-388 CH ₂ CH ₂ OMe-(CH ₂ ) ₂ -NMe- (CH ₂ ) ₂ -COtBu 1-389 CH ₂ OMe-(CH ₂ ) ₅ -COcPr 1-390 CH ₂ OMe Me Me COcPr 1-391 CH ₂ OMe Me Me COcPr (1-Me) 1-392 CH ₂ OMe Me Me COcPr (2-Me) 1- 393 CH ₂ OMe Me Me COcPr (1-Me, 2,2-Cl ₂ ) 1-394 CH ₂ OMe Me Me COcPr (1-CN) 1-395 CH ₂ OMe Me Me COcBu 1-396 CH ₂ OMe Me Me COcPent 1-397 CH ₂ OMe Me Me COCCl = CH ₂ 1-398 CH ₂ OMe Me Me CO (2-Cl-Ph) 1-399 CH ₂ OMe Me Me CO (2-Me-Ph) 1-400 CH ₂ OMe Me Me CO (2-OMe-Ph) 1-401 CH ₂ OMe Me Me CO (3-OMe-Ph) 1-402 CH ₂ OMe Me Me CO (4-OMe-Ph) 1-403 CH ₂ OMe Me Me CO (2-CF ₃ -Ph) 1-404 CH ₂ OMe Me Me CO (2,6- (OMe) ₂ -Ph) 1-405 CH ₂ OMe Me Me CO (2-OMe, 3-Me-Ph ) 1-406 CH ₂ OMe Me Me CO (2-OMe, 4-Me-Ph) 1-407 CH ₂ OMe Me Me CO (3,4,5- (OMe) ₃ -Ph) 1-408 CH ₂ OMe Me Me CO (5-Me-6-Chr) 1-409 CH ₂ OMe Me Me CO (5-Q ¹ ) 1-410 CH ₂ OEt Me Me COcPr 1-411 CH ₂ OEt Me Me COcPr (1-Me) 1-412 CH ₂ OEt Me Me COcPr (1-CN) 1-413 CH ₂ OEt Me Me COcPr (1- (4-OEt-Ph), 2,2-Cl ₂ ) 1-414 CH ₂ OEt Me Me COcBu 1-415 CH ₂ OEt Me Me COCCl = CH ₂ 1-416 CH ₂ OEt Me Me CO (2-Me-Ph) 1-417 CH ₂ OEt Me Me CO (2-OMe-Ph) 1-418 CH ₂ OEt Me Me CO (2-Cl-Ph) 1-419 CH ₂ OEt Me Me CO (3-OMe-Ph) 1-420 CH ₂ OEt Me Me CO (2-SMe-Ph) 1-421 CH ₂ OEt Me Me CO (3-Me-Ph) _{1-422 CH 2 OEt Me Me CO (} 3-CF 3 -Ph) 1-423 CH 2 OEt Me Me CO (3-CN-Ph) 1-424 CH 2 OEt Me Me CO (3-Cl-Ph) 1 -425 CH ₂ OEt Me Me CO (4-OMe-Ph) 1-426 CH ₂ OEt Me Me CO (4-Me-Ph) 1-427 CH ₂ OEt Me Me CO (3-Cl-Ph) 1-428 _{CH 2 OEt Me Me CO (2} -CF 3 -Ph) 1-429 CH 2 OEt Me Me CO (2-OPh-Ph) 1-430 CH 2 OEt Me Me CO (2-OEt-Ph) 1-431 CH ₂ OEt Me Me CO (2-OPr-Ph) 1-432 CH ₂ OEt Me Me CO (3-Pyr) 1-433 CH ₂ OEt Me Me CO (4-CF ₃ -3-Pyr) 1-434 CH ₂ OEt Me Me CO (2-SMe, 4-CF ₃ -5-Pym) 1-435 CH ₂ OEt Me Me CO (1-Me, 3-CF ₃ , 5-Cl-4-Pyza) 1-436 CH ₂ OEt Me Me CO (4-Me-5-Q ² ) 1-437 CH ₂ OEt Me Me CONMe ₂ 1-438 CH ₂ OEt Me Me CO (N-Mor) 1-439 CH ₂ OEt Me Me CH ₂ (4 -OMe-Ph) 1-440 CH ₂ CH ₂ OMe Me Me COcPr 1-441 CH ₂ CH ₂ OMe Me Me COcPr (1-Me) 1-442 CH ₂ CH ₂ OMe Me Me COcPr (1-CN) 1- 443 CH ₂ CH ₂ OMe Me Me COcBu 1-444 CH ₂ CH ₂ OMe Me Me COCCl = CH ₂ 1-445 CH ₂ CH ₂ OMe Me Me CO (2-Me-Ph) 1-446 CH ₂ CH ₂ OMe Me Me CO (2-SMe-Ph) 1-447 CH ₂ CH ₂ OMe Me Me CO (2-OMe-Ph) 1-448 CH ₂ CH ₂ OMe Me Me CO (2-Br-Ph) 1-449 CH ₂ CH ₂ OMe Me Me CO (2 -NO ₂ -Ph) 1-450 CH ₂ CH ₂ OMe Me Me CO (2-CF ₃ -Ph) 1-451 CH ₂ CH ₂ OMe Me Me CO (2-S (O) Me-Ph) 1-452 CH ₂ CH ₂ OMe Me Me CO (2-SO ₂ Me-Ph) 1-453 CH ₂ CH ₂ OMe Me Me CO (2-CH ₂ OPh-Ph) 1-454 CH ₂ CH ₂ OMe Me Me CO (2 -CO ₂ Me-Ph) 1-455 CH ₂ CH ₂ OMe Me Me CO (2-OPh-Ph) 1-456 CH ₂ CH ₂ OMe Me Me CO (2-OEt-Ph) 1-457 CH ₂ CH ₂ OMe Me Me CO (2-OPr-Ph) 1-458 CH ₂ CH ₂ OMe Me Me CO (2-OAc-Ph) 1-459 CH ₂ CH ₂ OMe Me Me CO (2-Me-3-Pyr) 1 -460 CH ₂ CH ₂ OMe Me Me CO (4-CF ₃ -3-Pyr) 1-461 CH ₂ CH ₂ OMe Me Me CO (2-SMe, 4-CF ₃ -5-Pym) 1-462 CH ₂ CH ₂ OMe Me Me CO (1-Me, 3-CF ₃ , 5-Cl-4-Pyza) 1-463 CH ₂ CH ₂ OMe Me Me CO (4-Me-5-Q ² ) 1-464 CH ₂ CH ₂ OMe Me Me CH ₂ Ph 1-465 CH ₂ CH ₂ OMe Me Me CH ₂ (4-OMe-Ph) 1-466 CH ₂ CH ₂ OMe Me Me CH ₂ OEt 1-467 Me Me Me COcPr 1-468 CH ₂ OMe Me CH ₂ CH = CH ₂ H 1-469 CH ₂ OMe Me CH ₂ CH = CH ₂ COcPr 1-470 CH ₂ OMe Me CH ₂ cHex H 1-471 CH ₂ OMe Me CH ₂ CH ₂ Ph H 1 -472 CH ₂ OMe Me CH ₂ CH ₂ CH = CH ₂ H 1-473 CH ₂ OMe Me CH ₂ CH ₂ OMe H 1-474 CH ₂ OMe Me (CH ₂ ) ₂ O (CH ₂ ) ₂ OMe H 1- 475 CH ₂ OMe-(CH ₂ ) ₄ -H ────────────────────────────────────

[0091]

[Table 2]

[0092]

Embedded image ──────────────────────────────────── Compound number (A) _n R ¹ R ⁴ ──── ──────────────────────────────── 2-1 2,4-Cl ₂ H COtBu 2-2 2,4- Cl ₂ Me H 2-3 2,4-Cl ₂ Me COtBu 2-4 2,4-Cl ₂ Me C (S) SEt 2-5 2,4-Cl ₂ Et H 2-6 2,4-Cl ₂ Et COtBu 2-7 2,4-Cl ₂ Et C (S) SEt 2-8 2,4-Cl ₂ CH ₂ OMe H 2-9 2,4-Cl ₂ CH ₂ OMe COtBu 2-10 2,4- Cl ₂ CH ₂ OMe C (S) SEt 2-11 2,4-Cl ₂ CH ₂ OEt H 2-12 2,4-Cl ₂ CH ₂ OEt COtBu 2-13 2,4-Cl ₂ CH ₂ OEt C ( S) SEt 2-14 2,4-Cl ₂ CH ₂ CH ₂ OMe H 2-15 2,4-Cl ₂ CH ₂ CH ₂ OMe COtBu 2-16 2,4-Cl ₂ CH ₂ CH ₂ OMe C (S ) SEt 2-17 2-Cl, 4-Me H COtBu 2-18 2-Cl, 4-Me Me H 2-19 2-Cl, 4-Me Me COtBu 2-20 2-Cl, 4-Me Me C (S) SEt 2-21 2-Cl, 4-Me Et H 2-22 2-Cl, 4-Me Et COtBu 2-23 2-Cl, 4-Me Et C (S) SEt 2-24 2-Cl , 4-Me CH ₂ OMe H 2-25 2-Cl, 4-Me CH ₂ OMe COtBu 2-26 2-Cl, 4-Me CH ₂ OMe C (S) SEt 2-27 2-Cl, 4-Me CH ₂ OEt H 2-28 2-Cl, 4-Me CH ₂ OEt COtBu 2-29 2-Cl, 4-Me CH ₂ OEt C (S) SEt 2-30 2-Cl, 4-Me CH ₂ CH ₂ OMe H 2-31 2-Cl, 4-Me CH ₂ CH ₂ OMe COtBu 2-32 2-Cl, 4-Me CH ₂ CH ₂ OMe C ( S) SEt 2-33 2,6-Me ₂ , 4-Br H COtBu 2-34 2,6-Me ₂ , 4-Br Me H 2-35 2,6-Me ₂ , 4-Br Me COtBu 2- 36 2,6-Me ₂ , 4-Br Me C (S) SEt 2-37 2,6-Me ₂ , 4-Br Et H 2-38 2,6-Me ₂ , 4-Br Et COtBu 2-39 2,6-Me ₂ , 4-Br Et C (S) SEt 2-40 2,6-Me ₂ , 4-Br CH ₂ OMe H 2-41 2,6-Me ₂ , 4-Br CH ₂ OMe COtBu 2-42 2,6-Me ₂ , 4-Br CH ₂ OMe C (S) SEt 2-43 2,6-Me ₂ , 4-Br CH ₂ OEt H 2-44 2,6-Me ₂ , 4- Br CH ₂ OEt COtBu 2-45 2,6-Me ₂ , 4-Br CH ₂ OEt C (S) SEt 2-46 2,6-Me ₂ ,, 4-Br CH ₂ CH ₂ OMe H 2-47 2, 6-Me ₂ , 4-Br CH ₂ CH ₂ OMe COtBu 2-48 2,6-Me ₂ , 4-Br CH ₂ CH ₂ OMe C (S) SEt 2-49 2,3-Me ₂ H COtBu 2- 50 2,3-Me ₂ Me H 2-51 2,3-Me ₂ Me COtBu 2-52 2,3-Me ₂ Me C (S) SEt 2-53 2,3-Me ₂ Et H 2-54 2 , 3-Me ₂ Et COtBu 2-55 2,3-Me ₂ Et C (S) SEt 2-56 2,3-Me ₂ CH ₂ OMe H 2-57 2,3-Me ₂ CH ₂ OMe COtBu 2- 58 2,3-Me ₂ CH ₂ OMe C (S) SEt 2-59 2,3-Me ₂ CH ₂ OEt H 2-60 2,3-Me ₂ CH ₂ OEt COtBu 2-61 2,3-Me ₂ CH ₂ OEt C (S) SEt 2-62 2,3-Me ₂ CH ₂ CH ₂ OMe H 2-63 2,3-Me ₂ C H ₂ CH ₂ OMe COtBu 2-64 2,3-Me ₂ CH ₂ CH ₂ OMe C (S) SEt 2-65 2,4-Me ₂ H COtBu 2-66 2,4-Me ₂ Me H 2-67 2,4-Me ₂ Me COtBu 2-68 2,4-Me ₂ Me C (S) SEt 2-69 2,4-Me ₂ Et H 2-70 2,4-Me ₂ Et COtBu 2-71 2, 4-Me ₂ Et C (S) SEt 2-72 2,4-Me ₂ CH ₂ OMe H 2-73 2,4-Me ₂ CH ₂ OMe COtBu 2-74 2,4-Me ₂ CH ₂ OMe C ( S) SEt 2-75 2,4-Me ₂ CH ₂ OEt H 2-76 2,4-Me ₂ CH ₂ OEt COtBu 2-77 2,4-Me ₂ CH ₂ OEt C (S) SEt 2-78 2 , 4-Me ₂ CH ₂ CH ₂ OMe H 2-79 2,4-Me ₂ CH ₂ CH ₂ OMe COtBu 2-80 2,4-Me ₂ CH ₂ CH ₂ OMe C (S) SEt 2-81 2, 5-Me ₂ H COtBu 2-82 2,5-Me ₂ Me H 2-83 2,5-Me ₂ Me COtBu 2-84 2,5-Me ₂ Me C (S) SEt 2-85 2,5- Me ₂ Et H 2-86 2,5-Me ₂ Et COtBu 2-87 2,5-Me ₂ Et C (S) SEt 2-88 2,5-Me ₂ CH ₂ OMe H 2-89 2,5- Me ₂ CH ₂ OMe COtBu 2-90 2,5-Me ₂ CH ₂ OMe C (S) SEt 2-91 2,5-Me ₂ CH ₂ OEt H 2-92 2,5-Me ₂ CH ₂ OEt COtBu 2 -93 2,5-Me ₂ CH ₂ OEt C (S) SEt 2-94 2,5-Me ₂ CH ₂ CH ₂ OMe H 2-95 2,5-Me ₂ CH ₂ CH ₂ OMe COtBu 2-96 2 , 5-Me ₂ CH ₂ CH ₂ OMe C (S) SEt 2-97 2,6-Me ₂ H COtBu 2-98 2,6-Me ₂ Me H 2-99 2,6-Me ₂ Me COtBu 2- 100 2,6-Me ₂ Me C (S) SEt 2-1 _{01 2,6-Me 2 Et H 2-102} 2,6-Me 2 Et COtBu 2-103 2,6-Me 2 Et C (S) SEt 2-104 2,6-Me 2 CH 2 OMe H 2- 105 2,6-Me ₂ CH ₂ OMe COtBu 2-106 2,6-Me ₂ CH ₂ OMe C (S) SEt 2-107 2,6-Me ₂ CH ₂ OEt H 2-108 2,6-Me ₂ CH ₂ OEt COtBu 2-109 2,6-Me ₂ CH ₂ OEt C (S) SEt 2-110 2,6-Me ₂ CH ₂ CH ₂ OMe H 2-111 2,6-Me ₂ CH ₂ CH ₂ OMe COtBu 2-112 2,6-Me ₂ CH ₂ CH ₂ OMe C (S) SEt 2-113 2-Me, 4-Br H COtBu 2-114 2-Me, 4-Br Me H 2-115 2-Me , 4-Br Me COtBu 2-116 2-Me, 4-Br Me C (S) SEt 2-117 2-Me, 4-Br Et H 2-118 2-Me, 4-Br Et COtBu 2-119 2 -Me, 4-Br Et C (S) SEt 2-120 2-Me, 4-Br CH ₂ OMe H 2-121 2-Me, 4-Br CH ₂ OMe COtBu 2-122 2-Me, 4-Br CH ₂ OMe C (S) SEt 2-123 2-Me, 4-Br CH ₂ OEt H 2-124 2-Me, 4-Br CH ₂ OEt COtBu 2-125 2-Me, 4-Br CH ₂ OEt C (S) SEt 2-126 2-Me, 4-Br CH ₂ CH ₂ OMe H 2-127 2-Me, 4-Br CH ₂ CH ₂ OMe COtBu 2-128 2-Me, 4-Br CH ₂ CH ₂ OMe C (S) SEt 2-129 2-Me, 6-Cl H COtBu 2-130 2-Me, 6-Cl Me H 2-131 2-Me, 6-Cl Me COtBu 2-132 2-Me, 6 -Cl Me C (S) SEt 2-133 2-Me, 6-Cl Et H 2-134 2-Me, 6-Cl Et COtBu 2-135 2-Me, 6-Cl Et C (S) SEt 2- 136 2-Me, 6-Cl CH ₂ OMe H 2-137 2-Me, 6-Cl CH ₂ OMe COtBu 2-138 2-Me, 6-Cl CH ₂ OMe C (S) SEt 2-139 2-Me, 6-Cl CH ₂ OEt H 2-140 2 -Me, 6-Cl CH ₂ OEt COtBu 2-141 2-Me, 6-Cl CH ₂ OEt C (S) SEt 2-142 2-Me, 6-Cl CH ₂ CH ₂ OMe H 2-143 2-Me , 6-Cl CH ₂ CH ₂ OMe COtBu 2-144 2-Me, 6-Cl CH ₂ CH ₂ OMe C (S) SEt 2-145 2-Me, 6-Br H COtBu 2-146 2-Me, 6 -Br Me H 2-147 2-Me, 6-Br Me COtBu 2-148 2-Me, 6-Br Me C (S) SEt 2-149 2-Me, 6-Br Et H 2-150 2-Me , 6-Br Et COtBu 2-151 2-Me, 6-Br Et C (S) SEt 2-152 2-Me, 6-Br CH ₂ OMe H 2-153 2-Me, 6-Br CH ₂ OMe COtBu 2-154 2-Me, 6-Br CH ₂ OMe C (S) SEt 2-155 2-Me, 6-Br CH ₂ OEt H 2-156 2-Me, 6-Br CH ₂ OEt COtBu 2-157 2 -Me, 6-Br CH ₂ OEt C (S) SEt 2-158 2-Me, 6-Br CH ₂ CH ₂ OMe H 2-159 2-Me, 6-Br CH ₂ CH ₂ OMe COtBu 2-160 2 -Me, 6-Br CH ₂ CH ₂ OMe C (S) SEt 2-161 2-Me, 4-OMe H COtBu 2-162 2-Me, 4-OMe Me H 2-163 2-Me, 4-OMe Me COtBu 2-164 2-Me, 4-OMe Me C (S) SEt 2-165 2-Me, 4-OMe Et H 2-166 2-Me, 4-OMe Et COtBu 2-167 2-Me, 4 -OMe Et C (S) SEt 2-168 2-Me, 4-OMe CH ₂ OMe H 2-169 2-Me, 4-OMe CH ₂ OMe COtBu 2-170 2-Me, 4-OMe CH ₂ OMe C (S) SEt 2-171 2-M e, 4-OMe CH ₂ OEt H 2-172 2-Me, 4-OMe CH ₂ OEt COtBu 2-173 2-Me, 4-OMe CH ₂ OEt C (S) SEt 2-174 2-Me, 4- OMe CH ₂ CH ₂ OMe H 2-175 2-Me, 4-OMe CH ₂ CH ₂ OMe COtBu 2-176 2-Me, 4-OMe CH ₂ CH ₂ OMe C (S) SEt 2-177 2-Me, 4-Ph H COtBu 2-178 2-Me, 4-Ph Me H 2-180 2-Me, 4-Ph Me C (S) SEt 2-181 2-Me, 4-Ph Et H 2-182 2- Me, 4-Ph Et COtBu 2-183 2-Me, 4-Ph Et C (S) SEt 2-184 2-Me, 4-Ph CH ₂ OMe H 2-185 2-Me, 4-Ph CH ₂ OMe COtBu 2-186 2-Me, 4-Ph CH ₂ OMe C (S) SEt 2-187 2-Me, 4-Ph CH ₂ OEt H 2-188 2-Me, 4-Ph CH ₂ OEt COtBu 2-189 2-Me, 4-Ph CH ₂ OEt C (S) SEt 2-190 2-Me, 4-Ph CH ₂ CH ₂ OMe H 2-191 2-Me, 4-Ph CH ₂ CH ₂ OMe COtBu 2-192 2-Me, 4-Ph CH ₂ CH ₂ OMe C (S) SEt 2-193 2,6-Me ₂ , 4-Ph H COtBu 2-194 2,6-Me ₂ , 4-Ph Me H 2-195 2,6-Me ₂ , 4-Ph Me COtBu 2-196 2,6-Me ₂ , 4-Ph Me C (S) SEt 2-197 2,6-Me ₂ , 4-Ph Et H 2-198 2 , 6-Me ₂ , 4-Ph Et COtBu 2-199 2,6-Me ₂ , 4-Ph Et C (S) SEt 2-200 2,6-Me ₂ , 4-Ph CH ₂ OMe H 2-201 2,6-Me ₂ , 4-Ph CH ₂ OMe COtBu 2-202 2,6-Me ₂ , 4-Ph CH ₂ OMe C (S) SEt 2-203 2,6-Me ₂ , 4-Ph CH ₂ OEt H 2-204 2,6-Me ₂ , 4-Ph CH ₂ OE t COtBu 2-205 2,6-Me ₂ , 4-Ph CH ₂ OEt C (S) SEt 2-206 2,6-Me ₂ , 4-Ph CH ₂ CH ₂ OMe H 2-207 2,6-Me ₂ , 4-Ph CH ₂ CH ₂ OMe COtBu 2-208 2,6-Me ₂ , 4-Ph CH ₂ CH ₂ OMe C (S) SEt 2-209 2,6-Me ₂ , 4-CN H COtBu 2 -210 2,6-Me ₂ , 4-CN Me H 2-211 2,6-Me ₂ , 4-CN Me COtBu 2-212 2,6-Me ₂ , 4-CN Me C (S) SEt 2- 213 2,6-Me ₂ , 4-CN Et H 2-214 2,6-Me ₂ , 4-CN Et COtBu 2-215 2,6-Me ₂ , 4-CN Et C (S) SEt 2-216 2,6-Me ₂ , 4-CN CH ₂ OMe H 2-217 2,6-Me ₂ , 4-CN CH ₂ OMe COtBu 2-218 2,6-Me ₂ , 4-CN CH ₂ OMe C (S ) SEt 2-219 2,6-Me ₂ ,, 4-CN CH ₂ OEt H 2-220 2,6-Me ₂ ,, 4-CN CH ₂ OEt COtBu 2-221 2,6-Me ₂ ,, 4-CN CH _{2 OEt C (S) SEt 2-222} 2,6-Me 2, 4-CN CH 2 CH 2 OMe H 2-223 2,6-Me 2, 4-CN CH 2 CH 2 OMe COtBu 2-224 2, 6-Me ₂ , 4-CN CH ₂ CH ₂ OMe C (S) SEt 2-225 2,3,6-Me ₃ H COtBu 2-226 2,3,6-Me ₃ Me H 2-227 2,3 , 6-Me ₃ Me COtBu 2-228 2,3,6-Me ₃ Me C (S) SEt 2-229 2,3,6-Me ₃ Et H 2-230 2,3,6-Me ₃ Et COtBu 2-231 2,3,6-Me ₃ Et C (S) SEt 2-232 2,3,6-Me ₃ CH ₂ OMe H 2-233 2,3,6-Me ₃ CH ₂ OMe COtBu 2-234 2,3,6-Me ₃ CH ₂ OMe C (S) SEt 2-235 2,3,6-Me ₃ CH ₂ OE t H 2-236 2,3,6-Me ₃ CH ₂ OEt COtBu 2-237 2,3,6-Me ₃ CH ₂ OEt C (S) SEt 2-238 2,3,6-Me ₃ CH ₂ CH ₂ OMe H 2-239 2,3,6-Me ₃ CH ₂ CH ₂ OMe COtBu 2-240 2,3,6-Me ₃ CH ₂ CH ₂ OMe C (S) SEt 2-241 2,3,4, 6-Me ₄ H COtBu 2-242 2,3,4,6-Me ₄ Me H 2-243 2,3,4,6-Me ₄ Me COtBu 2-244 2,3,4,6-Me ₄ Me C (S) SEt 2-245 2,3,4,6-Me ₄ Et H 2-246 2,3,4,6-Me ₄ Et COtBu 2-247 2,3,4,6-Me ₄ Et C (S) SEt 2-248 2,3,4,6-Me ₄ CH ₂ OMe H 2-249 2,3,4,6-Me ₄ CH ₂ OMe COtBu 2-250 2,3,4,6-Me ₄ CH ₂ OMe C (S) SEt 2-251 2,3,4,6-Me ₄ CH ₂ OEt H 2-252 2,3,4,6-Me ₄ CH ₂ OEt COtBu 2-253 2,3, 4,6-Me ₄ CH ₂ OEt C (S) SEt 2-254 2,3,4,6-Me ₄ CH ₂ CH ₂ OMe H 2-255 2,3,4,6-Me ₄ CH ₂ CH ₂ OMe COtBu 2-256 2,3,4,6-Me ₄ CH ₂ CH ₂ OMe C (S) SEt 2-257 2,4,6-Me ₃ , 3-Cl H COtBu 2-258 2,4,6 -Me ₃ ,, 3-Cl Me H 2-259 2,4,6-Me ₃ ,, 3-Cl Me COtBu 2-260 2,4,6-Me ₃ ,, 3-Cl Me C (S) SEt 2-261 2,4,6-Me ₃ , 3-Cl Et H 2-262 2,4,6-Me ₃ , 3-Cl Et COtBu 2-263 2,4,6-Me ₃ , 3-Cl Et C (S ) SEt 2-264 2,4,6-Me ₃ , 3-Cl CH ₂ OMe H 2-265 2,4,6-Me ₃ , 3-Cl CH ₂ OMe COtBu 2-266 2,4,6-Me _{3, 3-Cl} C H ₂ OMe C (S) SEt 2-267 2,4,6-Me ₃ ,, 3-Cl CH ₂ OEt H 2-268 2,4,6-Me ₃ ,, 3-Cl CH ₂ OEt COtBu 2-269 2 , 4,6-Me ₃ , 3-Cl CH ₂ OEt C (S) SEt 2-270 2,4,6-Me ₃ , 3-Cl CH ₂ CH ₂ OMe H 2-271 2,4,6-Me _{3, 3-Cl CH 2 CH} 2 OMe COtBu 2-272 2,4,6-Me 3, 3-Cl CH 2 CH 2 OMe C (S) SEt 2-273 2,6-Cl 2 H COtBu 2-274 2,6-Cl ₂ Me H 2-275 2,6-Cl ₂ Me COtBu 2-276 2,6-Cl ₂ Me C (S) SEt 2-277 2,6-Cl ₂ Et H 2-278 2, 6-Cl ₂ Et COtBu 2-279 2,6-Cl ₂ Et COCH ₂ tBu 2-280 2,6-Cl ₂ Et C (S) SEt 2-281 2,6-Cl ₂ CH ₂ OMe H 2-282 2,6-Cl ₂ CH ₂ OMe COtBu 2-283 2,6-Cl ₂ CH ₂ OMe C (S) SEt 2-284 2,6-Cl ₂ CH ₂ OEt H 2-285 2,6-Cl ₂ CH ₂ OEt COtBu 2-286 2,6-Cl ₂ CH ₂ OEt C (S) SEt 2-287 2,6-Cl ₂ CH ₂ CH ₂ OMe H 2-288 2,6-Cl ₂ CH ₂ CH ₂ OMe COtBu 2-289 2,6-Cl ₂ CH ₂ CH ₂ OMe C (S) SEt 2-290 2,5-Cl ₂ H COtBu 2-291 2,5-Cl ₂ Me H 2-292 2,5-Cl ₂ Me COtBu 2-293 2,5-Cl ₂ Me C (S) SEt 2-294 2,5-Cl ₂ Et H 2-295 2,5-Cl ₂ Et COtBu 2-296 2,5-Cl ₂ Et C (S) SEt 2-297 2,5-Cl ₂ CH ₂ OMe H 2-298 2,5-Cl ₂ CH ₂ OMe COtBu 2-299 2,5-Cl ₂ CH ₂ OMe C (S) SEt 2-300 2,5-Cl ₂ CH ₂ OEt H 2-301 2,5-Cl ₂ CH ₂ OEt COtBu 2-302 2,5-Cl ₂ CH ₂ OEt C (S) SEt 2-303 2,5-Cl ₂ CH ₂ CH ₂ OMe H 2-304 2 , 5-Cl ₂ CH ₂ CH ₂ OMe COtBu 2-305 2,5-Cl ₂ CH ₂ CH ₂ OMe C (S) SEt 2-306 3,5-Cl ₂ H COtBu 2-307 3,5-Cl ₂ Me H 2-308 3,5-Cl ₂ Me COtBu 2-309 3,5-Cl ₂ Me C (S) SEt 2-310 3,5-Cl ₂ Et H 2-311 3,5-Cl ₂ Et COtBu 2-312 3,5-Cl ₂ Et C (S) SEt 2-313 3,5-Cl ₂ CH ₂ OMe H 2-314 3,5-Cl ₂ CH ₂ OMe COtBu 2-315 3,5-Cl ₂ CH ₂ OMe C (S) SEt 2-316 3,5-Cl ₂ CH ₂ OEt H 2-317 3,5-Cl ₂ CH ₂ OEt COtBu 2-318 3,5-Cl ₂ CH ₂ OEt C (S) SEt 2-319 3,5-Cl ₂ CH ₂ CH ₂ OMe H 2-320 3,5-Cl ₂ CH ₂ CH ₂ OMe COtBu 2-321 3,5-Cl ₂ CH ₂ CH ₂ OMe C (S) SEt 2-322 2-Cl, 6-Br H COtBu 2-323 2-Cl, 6-Br Me H 2-324 2-Cl, 6-Br Me COtBu 2-325 2-Cl, 6-Br Me C (S ) SEt 2-326 2-Cl, 6-Br Et H 2-327 2-Cl, 6-Br Et COtBu 2-328 2-Cl, 6-Br Et C (S) SEt 2-329 2-Cl, 6 -Br CH ₂ OMe H 2-330 2-Cl, 6-Br CH ₂ OMe COtBu 2-331 2-Cl, 6-Br CH ₂ OMe C (S) SEt 2-332 2-Cl, 6-Br CH ₂ OEt H 2-333 2-Cl, 6-Br CH ₂ OEt COtBu 2-334 2-Cl, 6-Br CH ₂ OEt C (S) SEt 2-335 2-Cl, 6-Br CH ₂ CH ₂ OMe H 2-336 2-Cl, 6-Br CH ₂ CH ₂ OMe COtBu 2-337 2-Cl, 6-Br CH ₂ CH ₂ OMe C (S) SEt 2-338 2-Br H COtBu 2-339 2-Br Me H 2 -340 2-Br Me COtBu 2-341 2-Br Me C (S) SEt 2-342 2-Br Et H 2-343 2-Br Et COtBu 2-344 2-Br Et C (S) SEt 2-345 2-Br CH ₂ OMe H 2-346 2-Br CH ₂ OMe COtBu 2-347 2-Br CH ₂ OMe C (S) SEt 2-348 2-Br CH ₂ OEt H 2-349 2-Br CH ₂ OEt COtBu 2-350 2-Br CH ₂ OEt C (S) SEt 2-351 2-Br CH ₂ CH ₂ OMe H 2-352 2-Br CH ₂ CH ₂ OMe COtBu 2-353 2-Br CH ₂ CH ₂ OMe C (S) SEt 2-354 2-Br, 4-Me H COtBu 2-355 2-Br, 4-Me Me H 2-356 2-Br, 4-Me Me COtBu 2-357 2-Br, 4- Me Me C (S) SEt 2-358 2-Br, 4-Me Et H 2-359 2-Br, 4-Me Et COtBu 2-360 2-Br, 4-Me Et C (S) SEt 2-361 2-Br, 4-Me CH ₂ OMe H 2-362 2-Br, 4-Me CH ₂ OMe COtBu 2-363 2-Br, 4-Me CH ₂ OMe C (S) SEt 2-364 2-Br, 4-Me CH ₂ OEt H 2-365 2-Br, 4-Me CH ₂ OEt COtBu 2-366 2-Br, 4-Me CH ₂ OEt C (S) SEt 2-367 2-Br, 4-Me CH ₂ CH ₂ OMe H 2-368 2-Br, 4-Me CH ₂ CH ₂ OMe COtBu 2-369 2-Br, 4-Me CH ₂ CH ₂ OMe C (S) SEt 2-370 2,6-Cl ₂ , 4-CF ₃ H COtBu 2-371 2,6-Cl ₂ , 4-CF ₃ Me H 2-372 2,6-Cl ₂ , 4-CF ₃ Me COtBu 2-373 2,6-Cl ₂ , 4-CF ₃ Me C (S) SEt 2-374 2,6-Cl ₂ , 4-CF ₃ Et H 2-375 2,6-Cl ₂ , 4-CF ₃ Et COtBu 2 -376 2,6-Cl ₂ , 4-CF ₃ Et C (S) SEt 2-377 2,6-Cl ₂ , 4-CF ₃ CH ₂ OMe H 2-378 2,6-Cl ₂ , 4-CF ₃ CH ₂ OMe COtBu 2-379 2,6-Cl ₂ , 4-CF ₃ CH ₂ OMe C (S) SEt 2-380 2,6-Cl ₂ , 4-CF ₃ CH ₂ OEt H 2-381 2, 6-Cl ₂ , 4-CF ₃ CH ₂ OEt COtBu 2-382 2,6-Cl ₂ , 4-CF ₃ CH ₂ OEt C (S) SEt 2-383 2,6-Cl ₂ , 4-CF ₃ CH ₂ CH ₂ OMe H 2-384 2,6-Cl ₂ , 4-CF ₃ CH ₂ CH ₂ OMe COtBu 2-385 2,6-Cl ₂ , 4-CF ₃ CH ₂ CH ₂ OMe C (S) SEt 2 -386 2,4,6-Cl ₃ H COtBu 2-387 2,4,6-Cl ₃ Me H 2-388 2,4,6-Cl ₃ Me COtBu 2-389 2,4,6-Cl ₃ Me C (S) SEt 2-390 2,4,6-Cl ₃ Et H 2-391 2,4,6-Cl ₃ Et COtBu 2-392 2,4,6-Cl ₃ Et C (S) SEt 2- 393 2,4,6-Cl ₃ CH ₂ OMe H 2-394 2,4,6-Cl ₃ CH ₂ OMe COtBu 2-395 2,4,6-Cl ₃ CH ₂ OMe C (S) SEt 2-396 2,4,6-Cl ₃ CH ₂ OEt H 2-397 2,4,6-Cl ₃ CH ₂ OEt COtBu 2-398 2,4,6-Cl ₃ CH ₂ OEt C (S) SEt 2-399 2 , 4,6-Cl ₃ CH ₂ CH ₂ OMe H 2-400 2,4,6-Cl ₃ CH ₂ CH ₂ OMe COtBu 2-401 2,4,6-Cl ₃ CH ₂ CH ₂ OMe C (S) SEt 2-402 2,3,6-Cl ₃ H COtBu 2-403 2,3,6-Cl ₃ Me H 2-404 2,3,6-Cl ₃ Me COtBu 2-405 2,3,6-Cl ₃ Me C (S) SEt 2-406 2,3,6-Cl ₃ Et H 2-407 2,3,6-Cl ₃ Et COtBu 2-408 2,3,6-Cl ₃ Et C (S) SEt 2-409 2,3,6-Cl ₃ CH ₂ OMe H 2-410 2,3,6-Cl ₃ CH ₂ OMe COtBu 2-411 2,3,6-Cl ₃ CH ₂ OMe C (S) SEt 2-412 2,3,6-Cl ₃ CH ₂ OEt H 2-413 2,3,6-Cl ₃ CH ₂ OEt COtBu 2 -414 2,3,6-Cl ₃ CH ₂ OEt C (S) SEt 2-415 2,3,6-Cl ₃ CH ₂ CH ₂ OMe H 2-416 2,3,6-Cl ₃ CH ₂ CH ₂ OMe COtBu 2-417 2,3,6-Cl ₃ CH ₂ CH ₂ OMe C (S) SEt 2-418 2-Cl H COtBu 2-419 2-Cl Me H 2-420 2-Cl Me COtBu 2-421 2-Cl Me C (S) SEt 2-422 2-Cl Et H 2-423 2-Cl Et COtBu 2-424 2-Cl Et C (S) SEt 2-425 2-Cl CH ₂ OMe H 2-426 2-Cl CH ₂ OMe COtBu 2-427 2-Cl CH ₂ OMe C (S) SEt 2-428 2-Cl CH ₂ OEt H 2-429 2-Cl CH ₂ OEt COtBu 2-430 2-Cl CH ₂ OEt C (S) SEt 2-431 2-Cl CH ₂ CH ₂ OMe H 2-432 2-Cl CH ₂ CH ₂ OMe COtBu 2-433 2-Cl CH ₂ CH ₂ OMe C (S) SEt 2-434 2- Cl, 4-CF ₃ H COtBu 2-435 2-Cl, 4-CF ₃ Me H 2-436 2-Cl, 4-CF ₃ Me COtBu 2-437 2-Cl, 4-CF ₃ CH ₂ OMe H 2 -438 2-Cl, 4-CF ₃ CH ₂ OMe COtBu 2-439 2-Cl, 4-CF ₃ CH ₂ OEt H 2-441 2-Cl, 4-CF ₃ CH ₂ CH ₂ OMe H 2-442 2-Cl, 4-CF ₃ CH ₂ CH ₂ OMe COtBu 2-443 2,5-Br ₂ H COtBu 2-444 2,5-Br ₂ Me H 2-445 2,5-Br ₂ Me COtBu 2-446 2,5-Br ₂ CH ₂ OMe H 2-447 2,5-Br ₂ CH ₂ OMe COtBu 2-448 2,5-Br ₂ CH ₂ OEt H 2-449 2,5-Br ₂ CH ₂ OEt COtBu 2-450 2,5-Br ₂ CH ₂ CH ₂ OMe H 2-451 2,5-Br ₂ CH ₂ CH ₂ OMe COtBu 2-452 2-Br, 5-Me H COtBu 2-453 2- Br, 5-Me Me H 2-454 2-Br, 5-Me Me COtBu 2-455 2-Br, 5-Me CH ₂ OMe H 2-456 2-Br, 5-Me CH ₂ OMe COtBu 2-457 2-Br, 5-Me CH ₂ OEt H 2-458 2-Br, 5-Me CH ₂ OEt COtBu 2-459 2-Br, 5-Me CH ₂ CH ₂ OMe H 2-460 2-Br, 5- Me CH ₂ CH ₂ OMe COtBu 2-461 2-Me, 5-Br H COtBu 2-462 2-Me, 5-Br Me H 2-463 2-Me, 5-Br Me COtBu 2-464 2-Me, 5-Br CH ₂ OMe H 2-465 2-Me, 5-Br CH ₂ OMe COtBu 2-466 2-Me, 5-Br CH ₂ OEt H 2-467 2-Me, 5-Br CH ₂ OEt COtBu 2 -468 2-Me, 5-Br CH ₂ CH ₂ OMe H 2-469 2-Me, 5-Br CH ₂ CH ₂ OMe COtBu 2-470 3,5-Me ₂ H COtBu 2-471 3,5-Me ₂ Me H 2-472 3,5-Me ₂ Me COtBu 2-473 3,5-Me ₂ CH ₂ OMe H 2-474 3,5-Me ₂ CH ₂ OMe COtBu 2-475 3,5-Me ₂ CH ₂ OEt H 2-476 3,5-Me ₂ CH ₂ OEt COtBu 2-477 3,5-Me ₂ CH ₂ CH ₂ OM e H 2-478 3,5-Me ₂ CH ₂ CH ₂ OMe COtBu 2-479 2,6-Me ₂ ,, 3-Cl CH ₂ OMe H 2-480 2,6-Me ₂ ,, 3-Cl CH ₂ OMe COtBu 2-481 2,6-Me ₂ ,, 3-Cl CH ₂ OEt H 2-482 2,6-Me ₂ ,, 3-Cl CH ₂ OEt COtBu 2-483 2,6-Me ₂ ,, 3-Cl CH ₂ CH ₂ OMe H 2-484 2,6-Me ₂ ,, 3-Cl CH ₂ CH ₂ OMe COtBu 2-485 2,6-Me ₂ ,, 4-Cl CH ₂ OMe H 2-486 2,6-Me ₂ ,, 4-Cl CH ₂ OMe COtBu 2-487 2,6-Me ₂ ,, 4-Cl CH ₂ OEt H 2-488 2,6-Me ₂ ,, 4-Cl CH ₂ OEt COtBu 2-489 2,6-Me ₂ , 4-Cl CH ₂ CH ₂ OMe H 2-490 2,6-Me ₂ , 4-Cl CH ₂ CH ₂ OMe COtBu 2-491 2,4,6-Me ₃ , 3-Cl CH ₂ OMe H 2- 492 2,4,6-Me ₃ , 3-Cl CH ₂ OMe COtBu 2-493 2,4,6-Me ₃ , 3-Cl CH ₂ OEt H 2-494 2,4,6-Me ₃ , 3- Cl CH ₂ OEt COtBu 2-495 2,4,6-Me ₃ ,, 3-Cl CH ₂ CH ₂ OMe H 2-496 2,4,6-Me ₃ ,, 3-Cl CH ₂ CH ₂ OMe COtBu 2-497 2-Cl, 4,6-Me ₂ CH ₂ OMe H 2-498 2-Cl, 4,6-Me ₂ CH ₂ OMe COtBu 2-499 2-Cl, 4,6-Me ₂ CH ₂ OEt H 2- 500 2-Cl, 4,6-Me ₂ CH ₂ OEt COtBu 2-501 2-Cl, 4,6-Me ₂ CH ₂ CH ₂ OMe H 2-502 2-Cl, 4,6-Me ₂ CH ₂ CH ₂ OMe COtBu 2-503 2-Br, 4,6-Me ₂ CH ₂ OMe H 2-504 2-Br, 4,6-Me ₂ CH ₂ OMe COtBu 2-505 2-Br, 4,6-Me ₂ CH ₂ OEt H 2- 506 2-Br, 4,6-Me ₂ CH ₂ OEt COtBu 2-507 2-Br, 4,6-Me ₂ CH ₂ CH ₂ OMe H 2-508 2-Br, 4,6-Me ₂ CH ₂ CH ₂ OMe COtBu 2-509 2,4-Cl ₂ , 6-Me CH ₂ OMe H 2-510 2,4-Cl ₂ , 6-Me CH ₂ OMe COtBu 2-511 2,4-Cl ₂ , 6-Me CH ₂ OEt H 2-512 2,4-Cl ₂ , 6-Me CH ₂ OEt COtBu 2-513 2,4-Cl ₂ , 6-Me CH ₂ CH ₂ OMe H 2-514 2,4-Cl ₂ , 6-Me CH ₂ CH ₂ OMe COtBu 2-515 2-Me, 6-iPr CH ₂ OMe H 2-516 2-Me, 6-iPr CH ₂ OMe COtBu 2-517 2-Me, 6-iPr CH ₂ OEt H 2-518 2-Me, 6-iPr CH ₂ OEt COtBu 2-519 2-Me, 6-iPr CH ₂ CH ₂ OMe H 2-520 2-Me, 6-iPr CH ₂ CH ₂ OMe COtBu 2-521 2,6- (iPr) ₂ CH ₂ OMe H 2-522 2,6- (iPr) ₂ CH ₂ OMe COtBu 2-523 2,6- (iPr) ₂ CH ₂ OEt H 2-524 2,6- ( iPr) ₂ CH ₂ OEt COtBu 2-525 2,6- (iPr) ₂ CH ₂ CH ₂ OMe H 2-526 2,6- (iPr) ₂ CH ₂ CH ₂ OMe COtBu 2-527 2-Br, 5- Cl CH ₂ OMe H 2-528 2-Cl, 6-F CH ₂ OMe H 2-529 2-Cl, 6-F CH ₂ OMe COtBu 2-530 2-Cl, 6-F CH ₂ CH ₂ OMe H 2 -531 2-Cl, 6-F CH ₂ CH ₂ OMe COtBu 2-532 2-Cl, 6-F CH ₂ OEt H 2-533 2-Cl, 6-F CH ₂ OEt COtBu 2-534 2,3, 6-Me ₃ CH ₂ OMe COcPr 2-535 2-Me, 6-Et CH ₂ OMe H 2-536 2,3,4,6-Me ₄ CH ₂ O (C H ₂ ) ₂ OMe H 2-537 2,3,4,6-Me ₄ CH ₂ O (CH ₂ ) ₂ OMe COtBu 2-538 2,6-Me ₂ , 4-tBu CH ₂ OMe H 2-539 2 , 6-Me ₂ ,, 4-OMe CH ₂ OMe H 2-540 2,6-Me ₂ ,, 4-OMe CH ₂ OEt H 2-541 2,6-Me ₂ ,, 4-OPh CH ₂ OMe H 2-542 2,6-Me ₂ Pr H 2-543 2,6-Me ₂ iPr H 2-544 2,6-Me ₂ CH ₂ cPr H 2-545 2,6-Me ₂ CH ₂ C≡CH H 2-546 2,6-Me ₂ CH ₂ SMe H 2-547 2,6-Me ₂ CH ₂ SMe COtBu 2-548 2,6-Me ₂ CH ₂ CH ₂ OEt H 2-549 2,6-Me ₂ CH ₂ CH ₂ OEt COtBu 2-550 2,6-Me ₂ CH ₂ O (CH ₂ ) ₂ OMe H 2-551 2,6-Me ₂ CH ₂ CH ₂ CH ₂ OMe COtBu 2-552 2,6-Me ₂ CH ₂ CH (OMe) ₂ H 2-553 2,6-Me ₂ CH ₂ CH (OMe) ₂ COtBu 2-554 2,6-Me ₂ CH ₂ CH ₂ CH ₂ OMe H 2-555 2,6-Me ₂ CH (Me) CH ₂ OMe H 2-556 2,6-Me ₂ CH ₂ (3-Thf) H 2-557 2,6-Me ₂ 3-Thf H ───────────── ───────────────────────

[0093]

[Table 3]

[0094]

Embedded image ──────────────────────────────────── Compound number (A) _n R ¹ R ⁴ ──── ──────────────────────────────── 3-1 2,4-Cl ₂ H COtBu 3-2 2,4- Cl ₂ Me H 3-3 2,4-Cl ₂ Me COtBu 3-4 2,4-Cl ₂ Me C (S) SEt 3-5 2,4-Cl ₂ Et H 3-6 2,4-Cl ₂ Et COtBu 3-7 2,4-Cl ₂ Et C (S) SEt 3-8 2,4-Cl ₂ CH ₂ OMe H 3-9 2,4-Cl ₂ CH ₂ OMe COtBu 3-10 2,4- Cl ₂ CH ₂ OMe C (S) SEt 3-11 2,4-Cl ₂ CH ₂ OEt H 3-12 2,4-Cl ₂ CH ₂ OEt COtBu 3-13 2,4-Cl ₂ CH ₂ OEt C ( S) SEt 3-14 2,4-Cl ₂ CH ₂ CH ₂ OMe H 3-15 2,4-Cl ₂ CH ₂ CH ₂ OMe COtBu 3-16 2,4-Cl ₂ CH ₂ CH ₂ OMe C (S ) SEt 3-17 2-Cl, 4-Me H COtBu 3-18 2-Cl, 4-Me Me H 3-19 2-Cl, 4-Me Me COtBu 3-20 2-Cl, 4-Me Me C (S) SEt 3-21 2-Cl, 4-Me Et H 3-22 2-Cl, 4-Me Et COtBu 3-23 2-Cl, 4-Me Et C (S) SEt 3-24 2-Cl , 4-Me CH ₂ OMe H 3-25 2-Cl, 4-Me CH ₂ OMe COtBu 3-26 2-Cl, 4-Me CH ₂ OMe C (S) SEt 3-27 2-Cl, 4-Me CH ₂ OEt H 3-28 2-Cl, 4-Me CH ₂ OEt COtBu 3-29 2-Cl, 4-Me CH ₂ OEt C (S) SEt 3-30 2-Cl, 4-Me CH ₂ CH ₂ OMe H 3-31 2-Cl, 4-Me CH ₂ CH ₂ OMe COtBu 3-32 2-Cl, 4-Me CH ₂ CH ₂ OMe C ( S) SEt 3-33 2,6-Me ₂ , 4-Br H COtBu 3-34 2,6-Me ₂ , 4-Br Me H 3-35 2,6-Me ₂ , 4-Br Me COtBu 3- 36 2,6-Me ₂ , 4-Br Me C (S) SEt 3-37 2,6-Me ₂ , 4-Br Et H 3-38 2,6-Me ₂ , 4-Br Et COtBu 3-39 2,6-Me ₂ , 4-Br Et C (S) SEt 3-40 2,6-Me ₂ , 4-Br CH ₂ OMe H 3-41 2,6-Me ₂ , 4-Br CH ₂ OMe COtBu 3-42 2,6-Me ₂ , 4-Br CH ₂ OMe C (S) SEt 3-43 2,6-Me ₂ , 4-Br CH ₂ OEt H 3-44 2,6-Me ₂ , 4- Br CH ₂ OEt COtBu 3-45 2,6-Me ₂ ,, 4-Br CH ₂ OEt C (S) SEt 3-46 2,6-Me ₂ ,, 4-Br CH ₂ CH ₂ OMe H 3-47 2, 6-Me ₂ , 4-Br CH ₂ CH ₂ OMe COtBu 3-48 2,6-Me ₂ , 4-Br CH ₂ CH ₂ OMe C (S) SEt 3-49 2,3-Me ₂ H COtBu 3- 50 2,3-Me ₂ Me H 3-51 2,3-Me ₂ Me COtBu 3-52 2,3-Me ₂ Me C (S) SEt 3-53 2,3-Me ₂ Et H 3-54 2 , 3-Me ₂ Et COtBu 3-55 2,3-Me ₂ Et C (S) SEt 3-56 2,3-Me ₂ CH ₂ OMe H 3-57 2,3-Me ₂ CH ₂ OMe COtBu 3- 58 2,3-Me ₂ CH ₂ OMe C (S) SEt 3-59 2,3-Me ₂ CH ₂ OEt H 3-60 2,3-Me ₂ CH ₂ OEt COtBu 3-61 2,3-Me ₂ CH ₂ OEt C (S) SEt 3-62 2,3-Me ₂ CH ₂ CH ₂ OMe H 3-63 2,3-Me ₂ C H ₂ CH ₂ OMe COtBu 3-64 2,3-Me ₂ CH ₂ CH ₂ OMe C (S) SEt 3-65 2,4-Me ₂ H COtBu 3-66 2,4-Me ₂ Me H 3-67 2,4-Me ₂ Me COtBu 3-68 2,4-Me ₂ Me C (S) SEt 3-69 2,4-Me ₂ Et H 3-70 2,4-Me ₂ Et COtBu 3-71 2, 4-Me ₂ Et C (S) SEt 3-72 2,4-Me ₂ CH ₂ OMe H 3-73 2,4-Me ₂ CH ₂ OMe COtBu 3-74 2,4-Me ₂ CH ₂ OMe C ( S) SEt 3-75 2,4-Me ₂ CH ₂ OEt H 3-76 2,4-Me ₂ CH ₂ OEt COtBu 3-77 2,4-Me ₂ CH ₂ OEt C (S) SEt 3-78 2 , 4-Me ₂ CH ₂ CH ₂ OMe H 3-79 2,4-Me ₂ CH ₂ CH ₂ OMe COtBu 3-80 2,4-Me ₂ CH ₂ CH ₂ OMe C (S) SEt 3-81 2, 5-Me ₂ H COtBu 3-82 2,5-Me ₂ Me H 3-83 2,5-Me ₂ Me COtBu 3-84 2,5-Me ₂ Me C (S) SEt 3-85 2,5- Me ₂ Et H 3-86 2,5-Me ₂ Et COtBu 3-87 2,5-Me ₂ Et C (S) SEt 3-88 2,5-Me ₂ CH ₂ OMe H 3-89 2,5- Me ₂ CH ₂ OMe COtBu 3-90 2,5-Me ₂ CH ₂ OMe C (S) SEt 3-91 2,5-Me ₂ CH ₂ OEt H 3-92 2,5-Me ₂ CH ₂ OEt COtBu 3 -93 2,5-Me ₂ CH ₂ OEt C (S) SEt 3-94 2,5-Me ₂ CH ₂ CH ₂ OMe H 3-95 2,5-Me ₂ CH ₂ CH ₂ OMe COtBu 3-96 2 , 5-Me ₂ CH ₂ CH ₂ OMe C (S) SEt 3-97 2,6-Me ₂ H COtBu 3-98 2,6-Me ₂ Me H 3-99 2,6-Me ₂ Me COtBu 3- 100 2,6-Me ₂ Me C (S) SEt 3-1 01 2,6-Me ₂ Et H 3-102 2,6-Me ₂ Et COtBu 3-103 2,6-Me ₂ Et C (S) SEt 3-104 2,6-Me ₂ CH ₂ OMe H 3- 105 2,6-Me ₂ CH ₂ OMe COtBu 3-106 2,6-Me ₂ CH ₂ OMe C (S) SEt 3-107 2,6-Me ₂ CH ₂ OEt H 3-108 2,6-Me ₂ CH ₂ OEt COtBu 3-109 2,6-Me ₂ CH ₂ OEt C (S) SEt 3-110 2,6-Me ₂ CH ₂ CH ₂ OMe H 3-111 2,6-Me ₂ CH ₂ CH ₂ OMe COtBu 3-112 2,6-Me ₂ CH ₂ CH ₂ OMe C (S) SEt 3-113 2-Me, 4-Br H COtBu 3-114 2-Me, 4-Br Me H 3-115 2-Me , 4-Br Me COtBu 3-116 2-Me, 4-Br Me C (S) SEt 3-117 2-Me, 4-Br Et H 3-118 2-Me, 4-Br Et COtBu 3-119 2 -Me, 4-Br Et C (S) SEt 3-120 2-Me, 4-Br CH ₂ OMe H 3-121 2-Me, 4-Br CH ₂ OMe COtBu 3-122 2-Me, 4-Br CH ₂ OMe C (S) SEt 3-123 2-Me, 4-Br CH ₂ OEt H 3-124 2-Me, 4-Br CH ₂ OEt COtBu 3-125 2-Me, 4-Br CH ₂ OEt C (S) SEt 3-126 2-Me, 4-Br CH ₂ CH ₂ OMe H 3-127 2-Me, 4-Br CH ₂ CH ₂ OMe COtBu 3-128 2-Me, 4-Br CH ₂ CH ₂ OMe C (S) SEt 3-129 2-Me, 6-Cl H COtBu 3-130 2-Me, 6-Cl Me H 3-131 2-Me, 6-Cl Me COtBu 3-132 2-Me, 6 -Cl Me C (S) SEt 3-133 2-Me, 6-Cl Et H 3-134 2-Me, 6-Cl Et COtBu 3-135 2-Me, 6-Cl Et C (S) SEt 3- 136 2-Me, 6-Cl CH ₂ OMe H 3-137 2-Me, 6-Cl CH ₂ OMe COtBu 3-138 2-Me, 6-Cl CH ₂ OMe C (S) SEt 3-139 2-Me, 6-Cl CH ₂ OEt H 3-140 2 -Me, 6-Cl CH ₂ OEt COtBu 3-141 2-Me, 6-Cl CH ₂ OEt C (S) SEt 3-142 2-Me, 6-Cl CH ₂ CH ₂ OMe H 3-143 2-Me , 6-Cl CH ₂ CH ₂ OMe COtBu 3-144 2-Me, 6-Cl CH ₂ CH ₂ OMe C (S) SEt 3-145 2-Me, 6-Br H COtBu 3-146 2-Me, 6 -Br Me H 3-147 2-Me, 6-Br Me COtBu 3-148 2-Me, 6-Br Me C (S) SEt 3-149 2-Me, 6-Br Et H 3-150 2-Me , 6-Br Et COtBu 3-151 2-Me, 6-Br Et C (S) SEt 3-152 2-Me, 6-Br CH ₂ OMe H 3-153 2-Me, 6-Br CH ₂ OMe COtBu 3-154 2-Me, 6-Br CH ₂ OMe C (S) SEt 3-155 2-Me, 6-Br CH ₂ OEt H 3-156 2-Me, 6-Br CH ₂ OEt COtBu 3-157 2 -Me, 6-Br CH ₂ OEt C (S) SEt 3-158 2-Me, 6-Br CH ₂ CH ₂ OMe H 3-159 2-Me, 6-Br CH ₂ CH ₂ OMe COtBu 3-160 2 -Me, 6-Br CH ₂ CH ₂ OMe C (S) SEt 3-161 2-Me, 4-OMe H COtBu 3-162 2-Me, 4-OMe Me H 3-163 2-Me, 4-OMe Me COtBu 3-164 2-Me, 4-OMe Me C (S) SEt 3-165 2-Me, 4-OMe Et H 3-166 2-Me, 4-OMe Et COtBu 3-167 2-Me, 4 -OMe Et C (S) SEt 3-168 2-Me, 4-OMe CH ₂ OMe H 3-169 2-Me, 4-OMe CH ₂ OMe COtBu 3-170 2-Me, 4-OMe CH ₂ OMe C (S) SEt 3-171 2-M e, 4-OMe CH ₂ OEt H 3-172 2-Me, 4-OMe CH ₂ OEt COtBu 3-173 2-Me, 4-OMe CH ₂ OEt C (S) SEt 3-174 2-Me, 4- OMe CH ₂ CH ₂ OMe H 3-175 2-Me, 4-OMe CH ₂ CH ₂ OMe COtBu 3-176 2-Me, 4-OMe CH ₂ CH ₂ OMe C (S) SEt 3-177 2-Me, 4-Ph H COtBu 3-178 2-Me, 4-Ph Me H 3-179 2-Me, 4-Ph Me COtBu 3-180 2-Me, 4-Ph Me C (S) SEt 3-181 2- Me, 4-Ph Et H 3-182 2-Me, 4-Ph Et COtBu 3-183 2-Me, 4-Ph Et C (S) SEt 3-184 2-Me, 4-Ph CH ₂ OMe H 3 -185 2-Me, 4-Ph CH ₂ OMe COtBu 3-186 2-Me, 4-Ph CH ₂ OMe C (S) SEt 3-187 2-Me, 4-Ph CH ₂ OEt H 3-188 2- Me, 4-Ph CH ₂ OEt COtBu 3-189 2-Me, 4-Ph CH ₂ OEt C (S) SEt 3-190 2-Me, 4-Ph CH ₂ CH ₂ OMe H 3-191 2-Me, 4-Ph CH ₂ CH ₂ OMe COtBu 3-192 2-Me, 4-Ph CH ₂ CH ₂ OMe C (S) SEt 3-193 2,6-Me ₂ ,, 4-Ph H COtBu 3-194 2,6 _{-Me 2, 4-Ph Me H} 3-195 2,6-Me 2, 4-Ph Me COtBu 3-196 2,6-Me 2, 4-Ph Me C (S) SEt 3-197 2,6- _{Me 2, 4-Ph Et H} 3-198 2,6-Me 2, 4-Ph Et COtBu 3-199 2,6-Me 2, 4-Ph Et C (S) SEt 3-200 2,6-Me ₂ , 4-Ph CH ₂ OMe H 3-201 2,6-Me ₂ ,, 4-Ph CH ₂ OMe COtBu 3-202 2,6-Me ₂ ,, 4-Ph CH ₂ OMe C (S) SEt 3-203 2,6-Me ₂ , 4-Ph CH ₂ OEt H 3-204 2,6-Me ₂ , 4-Ph CH ₂ OEt COtBu 3-205 2,6-Me ₂ , 4-Ph CH ₂ OEt C (S) SEt 3-206 2,6-Me ₂ , 4-Ph CH _{2 CH 2 OMe H 3-207 2,6-Me} 2, 4-Ph CH 2 CH 2 OMe COtBu 3-208 2,6-Me 2, 4-Ph CH 2 CH 2 OMe C (S) SEt 3-209 2 , 6-Me ₂ , 4-CN H COtBu 3-210 2,6-Me ₂ , 4-CN Me H 3-211 2,6-Me ₂ , 4-CN Me COtBu 3-212 2,6-Me ₂ , 4-CN Me C (S) SEt 3-213 2,6-Me ₂ , 4-CN Et H 3-214 2,6-Me ₂ , 4-CN Et COtBu 3-215 2,6-Me ₂ , 4-CN Et C (S) SEt 3-216 2,6-Me ₂ , 4-CN CH ₂ OMe H 3-217 2,6-Me ₂ , 4-CN CH ₂ OMe COtBu 3-218 2,6- _{Me 2, 4-CN CH 2} OMe C (S) SEt 3-219 2,6-Me 2, 4-CN CH 2 OEt H 3-220 2,6-Me 2, 4-CN CH 2 OEt COtBu 3- 221 2,6-Me ₂ , 4-CN CH ₂ OEt C (S) SEt 3-222 2,6-Me ₂ , 4-CN CH ₂ CH ₂ OMe H 3-223 2,6-Me ₂ , 4- CN CH ₂ CH ₂ OMe COtBu 3-224 2,6-Me ₂ ,, 4-CN CH ₂ CH ₂ OMe C (S) SEt 3-225 2,3,6-Me ₃ H COtBu 3-226 2,3, 6-Me ₃ Me H 3-227 2,3,6-Me ₃ Me COtBu 3-228 2,3,6-Me ₃ Me C (S) SEt 3-229 2,3,6-Me ₃ Et H 3 -230 2,3,6-Me ₃ Et COtBu 3-231 2,3,6-Me ₃ Et C (S) SEt 3-232 2,3,6-Me ₃ CH ₂ OMe H 3-233 2,3 , 6-Me ₃ CH ₂ OMe COtBu 3-234 2,3,6-Me ₃ CH ₂ OMe C (S) SEt 3 -235 2,3,6-Me ₃ CH ₂ OEt H 3-236 2,3,6-Me ₃ CH ₂ OEt COtBu 3-237 2,3,6-Me ₃ CH ₂ OEt C (S) SEt 3- 238 2,3,6-Me ₃ CH ₂ CH ₂ OMe H 3-239 2,3,6-Me ₃ CH ₂ CH ₂ OMe COtBu 3-240 2,3,6-Me ₃ CH ₂ CH ₂ OMe C ( S) SEt 3-241 2,3,4,6-Me ₄ H COtBu 3-242 2,3,4,6-Me ₄ Me H 3-243 2,3,4,6-Me ₄ Me COtBu 3- 244 2,3,4,6-Me ₄ Me C (S) SEt 3-245 2,3,4,6-Me ₄ Et H 3-246 2,3,4,6-Me ₄ Et COtBu 3-247 2,3,4,6-Me ₄ Et C (S) SEt 3-248 2,3,4,6-Me ₄ CH ₂ OMe H 3-249 2,3,4,6-Me ₄ CH ₂ OMe COtBu 3-250 2,3,4,6-Me ₄ CH ₂ OMe C (S) SEt 3-251 2,3,4,6-Me ₄ CH ₂ OEt H 3-252 2,3,4,6-Me ₄ CH ₂ OEt COtBu 3-253 2,3,4,6-Me ₄ CH ₂ OEt C (S) SEt 3-254 2,3,4,6-Me ₄ CH ₂ CH ₂ OMe H 3-255 2, 3,4,6-Me ₄ CH ₂ CH ₂ OMe COtBu 3-256 2,3,4,6-Me ₄ CH ₂ CH ₂ OMe C (S) SEt 3-257 2,4,6-Me ₃ , 3 -Cl H COtBu 3-258 2,4,6-Me ₃ , 3-Cl Me H 3-259 2,4,6-Me ₃ , 3-Cl Me COtBu 3-260 2,4,6-Me ₃ , 3-Cl Me C (S) SEt 3-261 2,4,6-Me ₃ , 3-Cl Et H 3-262 2,4,6-Me ₃ , 3-Cl Et COtBu 3-263 2,4, 6-Me ₃ , 3-Cl Et C (S) SEt 3-264 2,4,6-Me ₃ , 3-Cl CH ₂ OMe H 3-265 2,4,6-Me ₃ , 3-Cl CH ₂ OMe COtBu 3 -266 2,4,6-Me ₃ , 3-Cl CH ₂ OMe C (S) SEt 3-267 2,4,6-Me ₃ , 3-Cl CH ₂ OEt H 3-268 2,4,6- Me ₃ , 3-Cl CH ₂ OEt COtBu 3-269 2,4,6-Me ₃ , 3-Cl CH ₂ OEt C (S) SEt 3-270 2,4,6-Me ₃ , 3-Cl CH ₂ CH ₂ OMe H 3-271 2,4,6-Me ₃ , 3-Cl CH ₂ CH ₂ OMe COtBu 3-272 2,4,6-Me ₃ , 3-Cl CH ₂ CH ₂ OMe C (S) SEt 3-273 2,6-Cl ₂ H COtBu 3-274 2,6-Cl ₂ Me H 3-275 2,6-Cl ₂ Me COtBu 3-276 2,6-Cl ₂ Me C (S) SEt 3- 277 2,6-Cl ₂ Et H 3-278 2,6-Cl ₂ Et COtBu 3-279 2,6-Cl ₂ Et COCH ₂ tBu 3-280 2,6-Cl ₂ Et C (S) SEt 3- 281 2,6-Cl ₂ CH ₂ OMe H 3-282 2,6-Cl ₂ CH ₂ OMe COtBu 3-283 2,6-Cl ₂ CH ₂ OMe C (S) SEt 3-284 2,6-Cl ₂ CH ₂ OEt H 3-285 2,6-Cl ₂ CH ₂ OEt COtBu 3-286 2,6-Cl ₂ CH ₂ OEt C (S) SEt 3-287 2,6-Cl ₂ CH ₂ CH ₂ OMe H 3 -288 2,6-Cl ₂ CH ₂ CH ₂ OMe COtBu 3-289 2,6-Cl ₂ CH ₂ CH ₂ OMe C (S) SEt 3-290 2,5-Cl ₂ H COtBu 3-291 2,5 -Cl ₂ Me H 3-292 2,5-Cl ₂ Me COtBu 3-293 2,5-Cl ₂ Me C (S) SEt 3-294 2,5-Cl ₂ Et H 3-295 2,5-Cl ₂ Et COtBu 3-296 2,5-Cl ₂ Et C (S) SEt 3-297 2,5-Cl ₂ CH ₂ OMe H 3-298 2,5-Cl ₂ CH ₂ OMe COtBu 3-299 2,5 -Cl ₂ CH ₂ OMe C (S) SEt 3-300 2,5-Cl ₂ CH ₂ OEt H 3-301 2,5-Cl ₂ CH ₂ OEt COtBu 3-302 2,5-Cl ₂ CH ₂ OEt C (S) SEt 3-303 2,5- Cl ₂ CH ₂ CH ₂ OMe H 3-305 2,5-Cl ₂ CH ₂ CH ₂ OMe C (S) SEt 3-306 3,5-Cl ₂ H COtBu 3-307 3,5-Cl ₂ Me H 3 -308 3,5-Cl ₂ Me COtBu 3-309 3,5-Cl ₂ Me C (S) SEt 3-310 3,5-Cl ₂ Et H 3-311 3,5-Cl ₂ Et COtBu 3-312 3,5-Cl ₂ Et C (S) SEt 3-313 3,5-Cl ₂ CH ₂ OMe H 3-314 3,5-Cl ₂ CH ₂ OMe COtBu 3-315 3,5-Cl ₂ CH ₂ OMe C (S) SEt 3-316 3,5-Cl ₂ CH ₂ OEt H 3-317 3,5-Cl ₂ CH ₂ OEt COtBu 3-318 3,5-Cl ₂ CH ₂ OEt C (S) SEt 3- 319 3,5-Cl ₂ CH ₂ CH ₂ OMe H 3-320 3,5-Cl ₂ CH ₂ CH ₂ OMe COtBu 3-321 3,5-Cl ₂ CH ₂ CH ₂ OMe C (S) SEt 3-322 2-Cl, 6-Br H COtBu 3-323 2-Cl, 6-Br Me H 3-324 2-Cl, 6-Br Me COtBu 3-325 2-Cl, 6-Br Me C (S) SEt 3 -326 2-Cl, 6-Br Et H 3-327 2-Cl, 6-Br Et COtBu 3-328 2-Cl, 6-Br Et C (S) SEt 3-329 2-Cl, 6-Br CH ₂ OMe H 3-330 2-Cl, 6-Br CH ₂ OMe COtBu 3-331 2-Cl, 6-Br CH ₂ OMe C (S) SEt 3-332 2-Cl, 6-Br CH ₂ OEt H 3 -333 2-Cl, 6-Br CH ₂ OEt COtBu 3-334 2-Cl, 6-Br CH ₂ OEt C (S) SEt 3-335 2-Cl, 6-Br CH ₂ CH ₂ OMe H 3-336 2-Cl, 6-Br CH ₂ CH ₂ OMe COtBu 3-337 2-Cl, 6-Br CH ₂ CH ₂ OMe C (S) SEt 3-338 2-Br H COtBu 3-339 2-Br Me H 3-340 2-Br Me COtBu 3-341 2-Br Me C (S) SEt 3-342 2-Br Et H 3-343 2-Br Et COtBu 3-344 2-Br Et C (S) SEt 3-345 2-Br CH ₂ OMe H 3-346 2-Br CH ₂ OMe COtBu 3-347 2-Br CH ₂ OMe C (S) SEt 3-348 2-Br CH ₂ OEt H 3-349 2-Br CH ₂ OEt COtBu 3-350 2-Br CH ₂ OEt C (S) SEt 3-351 2-Br CH ₂ CH ₂ OMe H 3-352 2-Br CH ₂ CH ₂ OMe COtBu 3-353 2-Br CH ₂ CH ₂ OMe C (S) SEt 3- 354 2-Br, 4-Me H COtBu 3-355 2-Br, 4-Me Me H 3-356 2-Br, 4-Me Me COtBu 3-357 2-Br, 4-Me Me C (S) SEt 3-358 2-Br, 4-Me Et H 3-359 2-Br, 4-Me Et COtBu 3-360 2-Br, 4-Me Et C (S) SEt 3-361 2-Br, 4-Me CH ₂ OMe H 3-362 2-Br, 4-Me CH ₂ OMe COtBu 3-363 2-Br, 4-Me CH ₂ OMe C (S) SEt 3-364 2-Br, 4-Me CH ₂ OEt H 3-365 2-Br, 4-Me CH ₂ OEt COtBu 3-366 2-Br, 4-Me CH ₂ OEt C (S) SEt 3-367 2-Br, 4-Me CH ₂ CH ₂ OMe H 3- 368 2-Br, 4-Me CH ₂ CH ₂ OMe COtBu 3-369 2-Br, 4-Me CH ₂ CH ₂ OMe C (S) SEt 3-370 2,6-Cl ₂ , 4-CF ₃ H COtBu 3-371 2,6-Cl ₂ , 4-CF ₃ Me H 3-372 2,6-Cl ₂ , 4-CF ₃ Me COtBu 3-373 2,6-Cl ₂ , 4-CF ₃ Me C (S) SEt 3-374 2,6-Cl ₂ , 4-CF ₃ Et H 3-375 2,6-Cl ₂ , 4-CF ₃ Et COtBu 3-376 2,6- Cl ₂ , 4-CF ₃ Et C (S) SEt 3-377 2,6-Cl ₂ , 4-CF ₃ CH ₂ OMe H 3-378 2,6-Cl ₂ , 4-CF ₃ CH ₂ OMe COtBu 3 -379 2,6-Cl ₂ , 4-CF ₃ CH ₂ OMe C (S) SEt 3-380 2,6-Cl ₂ , 4-CF ₃ CH ₂ OEt H 3-381 2,6-Cl ₂ , 4 -CF ₃ CH ₂ OEt COtBu 3-382 2,6-Cl ₂ , 4-CF ₃ CH ₂ OEt C (S) SEt 3-383 2,6-Cl ₂ , 4-CF ₃ CH ₂ CH ₂ OMe H 3 -384 2,6-Cl ₂ , 4-CF ₃ CH ₂ CH ₂ OMe COtBu 3-385 2,6-Cl ₂ , 4-CF ₃ CH ₂ CH ₂ OMe C (S) SEt 3-386 2,4, 6-Me ₃ H COtBu 3-387 2,4,6-Me ₃ Et H 3-388 2,4,6-Me ₃ Et COtBu 3-389 2,4,6-Me ₃ Et C (S) SEt 3 -392 2,4,6-Me ₃ CH ₂ OMe C (S) SEt 3-395 2,4,6-Me ₃ CH ₂ OEt C (S) SEt 3-396 2,4,6-Me ₃ CH ₂ CH ₂ OMe H 3-397 2,4,6-Me ₃ CH ₂ CH ₂ OMe COtBu 3-398 2,4,6-Me ₃ CH ₂ CH ₂ OMe C (S) SEt 3-399 2,4,6 -Cl ₃ H COtBu 3-400 2,4,6-Cl ₃ Me H 3-401 2,4,6-Cl ₃ Me COtBu 3-402 2,4,6-Cl ₃ Me C (S) SEt 3- 403 2,4,6-Cl ₃ Et H 3-404 2,4,6-Cl ₃ Et COtBu 3-405 2,4,6-Cl ₃ Et C (S) SEt 3-406 2,4,6- Cl ₃ CH ₂ OMe H 3-407 2,4,6-Cl ₃ CH ₂ OMe COtBu 3-408 2,4,6-Cl ₃ CH ₂ OMe C (S) SEt 3-409 2,4,6-Cl ₃ CH ₂ OEt H 3-410 2,4,6-Cl ₃ CH ₂ OEt COtBu 3-411 2,4,6-Cl ₃ CH ₂ OEt C (S) SEt 3-412 2,4,6-Cl ₃ CH ₂ CH ₂ OMe H 3-413 2,4,6-Cl ₃ CH ₂ CH ₂ OMe COtBu 3-414 2,4,6-Cl ₃ CH ₂ CH ₂ OMe C (S) SEt 3-415 2,3,6-Cl ₃ H COtBu 3-416 2,3,6-Cl ₃ Me H 3-417 2,3,6-Cl ₃ Me COtBu 3 -418 2,3,6-Cl ₃ Me C (S) SEt 3-419 2,3,6-Cl ₃ Et H 3-420 2,3,6-Cl ₃ Et COtBu 3-421 2,3,6 -Cl ₃ Et C (S) SEt 3-422 2,3,6-Cl ₃ CH ₂ OMe H 3-423 2,3,6-Cl ₃ CH ₂ OMe COtBu 3-424 2,3,6-Cl ₃ CH ₂ OMe C (S) SEt 3-425 2,3,6-Cl ₃ CH ₂ OEt H 3-426 2,3,6-Cl ₃ CH ₂ OEt COtBu 3-427 2,3,6-Cl ₃ CH ₂ OEt C (S) SEt 3-428 2,3,6-Cl ₃ CH ₂ CH ₂ OMe H 3-429 2,3,6-Cl ₃ CH ₂ CH ₂ OMe COtBu 3-430 2,3,6- Cl ₃ CH ₂ CH ₂ OMe C (S) SEt 3-431 2-Cl H COtBu 3-432 2-Cl Me H 3-433 2-Cl Me COtBu 3-434 2-Cl Me C (S) SEt 3- 435 2-Cl Et H 3-436 2-Cl Et COtBu 3-437 2-Cl Et C (S) SEt 3-438 2-Cl CH ₂ OMe H 3-439 2-Cl CH ₂ OMe COtBu 3-440 2 -Cl CH ₂ OMe C (S) SEt 3-441 2-Cl CH ₂ OEt H 3-442 2-Cl CH ₂ OEt COtBu 3-443 2-Cl CH ₂ OEt C (S) SEt 3-444 2-Cl CH ₂ CH ₂ OM e H 3-445 2-Cl CH ₂ CH ₂ OMe COtBu 3-446 2-Cl CH ₂ CH ₂ OMe C (S) SEt 3-447 2-Cl, 4-CF ₃ H COtBu 3-448 2-Cl, 4-CF ₃ Me H 3-449 2-Cl, 4-CF ₃ Me COtBu 3-450 2-Cl, 4-CF ₃ CH ₂ OMe H 3-451 2-Cl, 4-CF ₃ CH ₂ OMe COtBu 3 -452 2-Cl, 4-CF ₃ CH ₂ OEt H 3-453 2-Cl, 4-CF ₃ CH ₂ OEt COtBu 3-454 2-Cl, 4-CF ₃ CH ₂ CH ₂ OMe H 3-455 2 -Cl, 4-CF ₃ CH ₂ CH ₂ OMe COtBu 3-456 2,5-Br ₂ H COtBu 3-457 2,5-Br ₂ Me H 3-458 2,5-Br ₂ Me COtBu 3-459 2 , 5-Br ₂ CH ₂ OMe H 3-460 2,5-Br ₂ CH ₂ OMe COtBu 3-461 2,5-Br ₂ CH ₂ OEt H 3-462 2,5-Br ₂ CH ₂ OEt COtBu 3- 463 2,5-Br ₂ CH ₂ CH ₂ OMe H 3-464 2,5-Br ₂ CH ₂ CH ₂ OMe COtBu 3-465 2-Br, 5-Me H COtBu 3-466 2-Br, 5-Me Me H 3-467 2-Br, 5-Me Me COtBu 3-468 2-Br, 5-Me CH ₂ OMe H 3-469 2-Br, 5-Me CH ₂ OMe COtBu 3-470 2-Br, 5 -Me CH ₂ OEt H 3-471 2-Br, 5-Me CH ₂ OEt COtBu 3-472 2-Br, 5-Me CH ₂ CH ₂ OMe H 3-473 2-Br, 5-Me CH ₂ CH ₂ OMe COtBu 3-474 2-Me, 5-Br H COtBu 3-475 2-Me, 5-Br Me H 3-476 2-Me, 5-Br Me COtBu 3-477 2-Me, 5-Br CH ₂ OMe H 3-478 2-Me, 5-Br CH ₂ OMe COtBu 3-479 2-Me, 5-Br CH ₂ OEt H 3-480 2-Me, 5-Br CH ₂ OEt COtBu 3-481 2-Me, 5-Br CH ₂ CH ₂ OMe H 3-482 2-Me, 5-Br CH ₂ CH ₂ OMe COtBu 3-483 3,5- Me ₂ H COtBu 3-484 3,5-Me ₂ Me H 3-485 3,5-Me ₂ Me COtBu 3-486 3,5-Me ₂ CH ₂ OMe H 3-487 3,5-Me ₂ CH ₂ OMe COtBu 3-488 3,5-Me ₂ CH ₂ OEt H 3-489 3,5-Me ₂ CH ₂ OEt COtBu 3-490 3,5-Me ₂ CH ₂ CH ₂ OMe H 3-491 3,5- _{Me 2 CH 2 CH 2 OMe COtBu} 3-492 2,6-Me 2, 3-Cl CH 2 OMe H 3-493 2,6-Me 2, 3-Cl CH 2 OMe COtBu 3-494 2,6-Me ₂ , 3-Cl CH ₂ OEt H 3-495 2,6-Me ₂ ,, 3-Cl CH ₂ OEt COtBu 3-496 2,6-Me ₂ ,, 3-Cl CH ₂ CH ₂ OMe H 3-497 2, 6-Me ₂ ,, 3-Cl CH ₂ CH ₂ OMe COtBu 3-498 2,6-Me ₂ ,, 4-Cl CH ₂ OMe H 3-499 2,6-Me ₂ ,, 4-Cl CH ₂ OMe COtBu 3- 500 2,6-Me ₂ , 4-Cl CH ₂ OEt H 3-501 2,6-Me ₂ ,, 4-Cl CH ₂ OEt COtBu 3-502 2,6-Me ₂ ,, 4-Cl CH ₂ CH ₂ OMe H 3-503 2,6-Me ₂ , 4-Cl CH ₂ CH ₂ OMe COtBu 3-504 2,4,6-Me ₃ , 3-Cl CH ₂ OMe H 3-505 2,4,6-Me ₃ , 3-Cl CH ₂ OMe COtBu 3-506 2,4,6-Me ₃ , 3-Cl CH ₂ OEt H 3-507 2,4,6-Me ₃ ,, 3-Cl CH ₂ OEt COtBu 3-508 2 , 4,6-Me ₃ , 3-Cl CH ₂ CH ₂ OMe H 3-509 2,4,6-Me ₃ , 3-Cl CH ₂ CH ₂ OMe COtBu 3-510 2- Cl, 4,6-Me ₂ CH ₂ OMe H 3-511 2-Cl, 4,6-Me ₂ CH ₂ OMe COtBu 3-512 2-Cl, 4,6-Me ₂ CH ₂ OEt H 3-513 2 -Cl, 4,6-Me ₂ CH ₂ OEt COtBu 3-514 2-Cl, 4,6-Me ₂ CH ₂ CH ₂ OMe H 3-515 2-Cl, 4,6-Me ₂ CH ₂ CH ₂ OMe COtBu 3-516 2-Br, 4,6-Me ₂ CH ₂ OMe H 3-517 2-Br, 4,6-Me ₂ CH ₂ OMe COtBu 3-518 2-Br, 4,6-Me ₂ CH ₂ OEt H 3-519 2-Br, 4,6-Me ₂ CH ₂ OEt COtBu 3-520 2-Br, 4,6-Me ₂ CH ₂ CH ₂ OMe H 3-521 2-Br, 4,6-Me ₂ CH ₂ CH ₂ OMe COtBu 3-522 2,4-Cl ₂ , 6-Me CH ₂ OMe H 3-523 2,4-Cl ₂ , 6-Me CH ₂ OMe COtBu 3-524 2,4-Cl ₂ , 6-Me CH ₂ OEt H 3-525 2,4-Cl ₂ , 6-Me CH ₂ OEt COtBu 3-526 2,4-Cl ₂ , 6-Me CH ₂ CH ₂ OMe H 3-527 2,4 -Cl ₂ , 6-Me CH ₂ CH ₂ OMe COtBu 3-528 2-Me, 6-iPr CH ₂ OMe H 3-529 2-Me, 6-iPr CH ₂ OMe COtBu 3-530 2-Me, 6- iPr CH ₂ OEt H 3-531 2-Me, 6-iPr CH ₂ OEt COtBu 3-532 2-Me, 6-iPr CH ₂ CH ₂ OMe H 3-533 2-Me, 6-iPr CH ₂ CH ₂ OMe COtBu 3-534 2,6- (iPr) ₂ CH ₂ OMe H 3-535 2,6- (iPr) ₂ CH ₂ OMe COtBu 3-536 2,6- (iPr) ₂ CH ₂ OEt H 3-537 2 , 6- (iPr) ₂ CH ₂ OEt COtBu 3-538 2,6- (iPr) ₂ CH ₂ CH ₂ OMe H 3-539 2,6- (iPr) ₂ CH ₂ CH ₂ OM e COtBu ────────────────────────────────────

[0095]

[Table 4]

[0096]

Embedded image ──────────────────────────────────── Compound number (A) _n R ¹ R ⁴ ──── ──────────────────────────────── 4-1 2,4-Cl ₂ H COtBu 4-2 2,4- Cl ₂ Me H 4-3 2,4-Cl ₂ Me COtBu 4-4 2,4-Cl ₂ Me C (S) SEt 4-5 2,4-Cl ₂ Et H 4-6 2,4-Cl ₂ Et COtBu 4-7 2,4-Cl ₂ Et C (S) SEt 4-8 2,4-Cl ₂ CH ₂ OMe H 4-9 2,4-Cl ₂ CH ₂ OMe COtBu 4-10 2,4- Cl ₂ CH ₂ OMe C (S) SEt 4-11 2,4-Cl ₂ CH ₂ OEt H 4-12 2,4-Cl ₂ CH ₂ OEt COtBu 4-13 2,4-Cl ₂ CH ₂ OEt C ( S) SEt 4-14 2,4-Cl ₂ CH ₂ CH ₂ OMe H 4-15 2,4-Cl ₂ CH ₂ CH ₂ OMe COtBu 4-16 2,4-Cl ₂ CH ₂ CH ₂ OMe C (S ) SEt 4-17 2-Cl, 4-Me H COtBu 4-18 2-Cl, 4-Me Me H 4-19 2-Cl, 4-Me Me COtBu 4-20 2-Cl, 4-Me Me C (S) SEt 4-21 2-Cl, 4-Me Et H 4-22 2-Cl, 4-Me Et COtBu 4-23 2-Cl, 4-Me Et C (S) SEt 4-24 2-Cl , 4-Me CH ₂ OMe H 4-25 2-Cl, 4-Me CH ₂ OMe COtBu 4-26 2-Cl, 4-Me CH ₂ OMe C (S) SEt 4-27 2-Cl, 4-Me CH ₂ OEt H 4-28 2-Cl, 4-Me CH ₂ OEt COtBu 4-29 2-Cl, 4-Me CH ₂ OEt C (S) SEt 4-30 2-Cl, 4-Me CH ₂ CH ₂ OMe H 4-31 2-Cl, 4-Me CH ₂ CH ₂ OMe COtBu 4-32 2-Cl, 4-Me CH ₂ CH ₂ OMe C ( S) SEt 4-33 2,6-Me ₂ , 4-Br H COtBu 4-34 2,6-Me ₂ , 4-Br Me H 4-35 2,6-Me ₂ , 4-Br Me COtBu 4- 36 2,6-Me ₂ , 4-Br Me C (S) SEt 4-37 2,6-Me ₂ , 4-Br Et H 4-38 2,6-Me ₂ , 4-Br Et COtBu 4-39 2,6-Me ₂ , 4-Br Et C (S) SEt 4-40 2,6-Me ₂ , 4-Br CH ₂ OMe H 4-41 2,6-Me ₂ , 4-Br CH ₂ OMe COtBu 4-42 2,6-Me ₂ , 4-Br CH ₂ OMe C (S) SEt 4-43 2,6-Me ₂ , 4-Br CH ₂ OEt H 4-44 2,6-Me ₂ , 4- _{Br CH 2 OEt COtBu 4-45 2,6-} Me 2, 4-Br CH 2 OEt C (S) SEt 4-46 2,6-Me 2, 4-Br CH 2 CH 2 OMe H 4-47 2, 6-Me ₂ , 4-Br CH ₂ CH ₂ OMe COtBu 4-48 2,6-Me ₂ ,, 4-Br CH ₂ CH ₂ OMe C (S) SEt 4-49 2,3-Me ₂ H COtBu 4- 50 2,3-Me ₂ Me H 4-51 2,3-Me ₂ Me COtBu 4-52 2,3-Me ₂ Me C (S) SEt 4-53 2,3-Me ₂ Et H 4-54 2 , 3-Me ₂ Et COtBu 4-55 2,3-Me ₂ Et C (S) SEt 4-56 2,3-Me ₂ CH ₂ OMe H 4-57 2,3-Me ₂ CH ₂ OMe COtBu 4- 58 2,3-Me ₂ CH ₂ OMe C (S) SEt 4-59 2,3-Me ₂ CH ₂ OEt H 4-60 2,3-Me ₂ CH ₂ OEt COtBu 4-61 2,3-Me ₂ CH ₂ OEt C (S) SEt 4-62 2,3-Me ₂ CH ₂ CH ₂ OMe H 4-63 2,3-Me ₂ C H ₂ CH ₂ OMe COtBu 4-64 2,3-Me ₂ CH ₂ CH ₂ OMe C (S) SEt 4-65 2,4-Me ₂ H COtBu 4-66 2,4-Me ₂ Me H 4-67 2,4-Me ₂ Me COtBu 4-68 2,4-Me ₂ Me C (S) SEt 4-69 2,4-Me ₂ Et H 4-70 2,4-Me ₂ Et COtBu 4-71 2, 4-Me ₂ Et C (S) SEt 4-72 2,4-Me ₂ CH ₂ OMe H 4-73 2,4-Me ₂ CH ₂ OMe COtBu 4-74 2,4-Me ₂ CH ₂ OMe C ( S) SEt 4-75 2,4-Me ₂ CH ₂ OEt H 4-76 2,4-Me ₂ CH ₂ OEt COtBu 4-77 2,4-Me ₂ CH ₂ OEt C (S) SEt 4-78 2 , 4-Me ₂ CH ₂ CH ₂ OMe H 4-79 2,4-Me ₂ CH ₂ CH ₂ OMe COtBu 4-80 2,4-Me ₂ CH ₂ CH ₂ OMe C (S) SEt 4-81 2, 5-Me ₂ H COtBu 4-82 2,5-Me ₂ Me H 4-83 2,5-Me ₂ Me COtBu 4-84 2,5-Me ₂ Me C (S) SEt 4-85 2,5- Me ₂ Et H 4-86 2,5-Me ₂ Et COtBu 4-87 2,5-Me ₂ Et C (S) SEt 4-88 2,5-Me ₂ CH ₂ OMe H 4-89 2,5- _{Me 2 CH 2 OMe COtBu 4-90 2,5} -Me 2 CH 2 OMe C (S) SEt 4-91 2,5-Me 2 CH 2 OEt H 4-92 2,5-Me 2 CH 2 OEt COtBu 4 -93 2,5-Me ₂ CH ₂ OEt C (S) SEt 4-94 2,5-Me ₂ CH ₂ CH ₂ OMe H 4-95 2,5-Me ₂ CH ₂ CH ₂ OMe COtBu 4-96 2 , 5-Me ₂ CH ₂ CH ₂ OMe C (S) SEt 4-97 2,6-Me ₂ H COtBu 4-98 2,6-Me ₂ Me H 4-99 2,6-Me ₂ Me COtBu 4- 100 2,6-Me ₂ Me C (S) SEt 4-1 01 2,6-Me ₂ Et H 4-102 2,6-Me ₂ Et COtBu 4-103 2,6-Me ₂ Et C (S) SEt 4-104 2,6-Me ₂ CH ₂ OMe H 4- 105 2,6-Me ₂ CH ₂ OMe COtBu 4-106 2,6-Me ₂ CH ₂ OMe C (S) SEt 4-107 2,6-Me ₂ CH ₂ OEt H 4-108 2,6-Me ₂ CH ₂ OEt COtBu 4-109 2,6-Me ₂ CH ₂ OEt C (S) SEt 4-110 2,6-Me ₂ CH ₂ CH ₂ OMe H 4-111 2,6-Me ₂ CH ₂ CH ₂ OMe COtBu 4-112 2,6-Me ₂ CH ₂ CH ₂ OMe C (S) SEt 4-113 2-Me, 4-Br H COtBu 4-114 2-Me, 4-Br Me H 4-115 2-Me , 4-Br Me COtBu 4-116 2-Me, 4-Br Me C (S) SEt 4-117 2-Me, 4-Br Et H 4-118 2-Me, 4-Br Et COtBu 4-119 2 -Me, 4-Br Et C (S) SEt 4-120 2-Me, 4-Br CH ₂ OMe H 4-121 2-Me, 4-Br CH ₂ OMe COtBu 4-122 2-Me, 4-Br _{CH 2 OMe C (S) SEt} 4-123 2-Me, 4-Br CH 2 OEt H 4-124 2-Me, 4-Br CH 2 OEt COtBu 4-125 2-Me, 4-Br CH 2 OEt C (S) SEt 4-126 2-Me, 4-Br CH ₂ CH ₂ OMe H 4-127 2-Me, 4-Br CH ₂ CH ₂ OMe COtBu 4-128 2-Me, 4-Br CH ₂ CH ₂ OMe C (S) SEt 4-129 2-Me, 6-Cl H COtBu 4-130 2-Me, 6-Cl Me H 4-131 2-Me, 6-Cl Me COtBu 4-132 2-Me, 6 -Cl Me C (S) SEt 4-133 2-Me, 6-Cl Et H 4-134 2-Me, 6-Cl Et COtBu 4-135 2-Me, 6-Cl Et C (S) SEt 4- 136 2-Me, 6-Cl CH ₂ OMe H 4-137 2-Me, 6-Cl CH ₂ OMe COtBu 4-138 2-Me, 6-Cl CH ₂ OMe C (S) SEt 4-139 2-Me, 6-Cl CH ₂ OEt H 4-140 2 -Me, 6-Cl CH ₂ OEt COtBu 4-141 2-Me, 6-Cl CH ₂ OEt C (S) SEt 4-142 2-Me, 6-Cl CH ₂ CH ₂ OMe H 4-143 2-Me , 6-Cl CH ₂ CH ₂ OMe COtBu 4-144 2-Me, 6-Cl CH ₂ CH ₂ OMe C (S) SEt 4-145 2-Me, 6-Br H COtBu 4-146 2-Me, 6 -Br Me H 4-147 2-Me, 6-Br Me COtBu 4-148 2-Me, 6-Br Me C (S) SEt 4-149 2-Me, 6-Br Et H 4-150 2-Me , 6-Br Et COtBu 4-151 2-Me, 6-Br Et C (S) SEt 4-152 2-Me, 6-Br CH ₂ OMe H 4-153 2-Me, 6-Br CH ₂ OMe COtBu 4-154 2-Me, 6-Br CH ₂ OMe C (S) SEt 4-155 2-Me, 6-Br CH ₂ OEt H 4-156 2-Me, 6-Br CH ₂ OEt COtBu 4-157 2 -Me, 6-Br CH ₂ OEt C (S) SEt 4-158 2-Me, 6-Br CH ₂ CH ₂ OMe H 4-159 2-Me, 6-Br CH ₂ CH ₂ OMe COtBu 4-160 2 -Me, 6-Br CH ₂ CH ₂ OMe C (S) SEt 4-161 2-Me, 4-OMe H COtBu 4-162 2-Me, 4-OMe Me H 4-163 2-Me, 4-OMe Me COtBu 4-164 2-Me, 4-OMe Me C (S) SEt 4-165 2-Me, 4-OMe Et H 4-166 2-Me, 4-OMe Et COtBu 4-167 2-Me, 4 -OMe Et C (S) SEt 4-168 2-Me, 4-OMe CH ₂ OMe H 4-169 2-Me, 4-OMe CH ₂ OMe COtBu 4-170 2-Me, 4-OMe CH ₂ OMe C (S) SEt 4-171 2-M e, 4-OMe CH ₂ OEt H 4-172 2-Me, 4-OMe CH ₂ OEt COtBu 4-173 2-Me, 4-OMe CH ₂ OEt C (S) SEt 4-174 2-Me, 4- OMe CH ₂ CH ₂ OMe H 4-175 2-Me, 4-OMe CH ₂ CH ₂ OMe COtBu 4-176 2-Me, 4-OMe CH ₂ CH ₂ OMe C (S) SEt 4-177 2-Me, 4-Ph H COtBu 4-178 2-Me, 4-Ph Me H 4-179 2-Me, 4-Ph Me COtBu 4-180 2-Me, 4-Ph Me C (S) SEt 4-181 2- Me, 4-Ph Et H 4-182 2-Me, 4-Ph Et COtBu 4-183 2-Me, 4-Ph Et C (S) SEt 4-184 2-Me, 4-Ph CH ₂ OMe H 4 -185 2-Me, 4-Ph CH ₂ OMe COtBu 4-186 2-Me, 4-Ph CH ₂ OMe C (S) SEt 4-187 2-Me, 4-Ph CH ₂ OEt H 4-188 2- Me, 4-Ph CH ₂ OEt COtBu 4-189 2-Me, 4-Ph CH ₂ OEt C (S) SEt 4-190 2-Me, 4-Ph CH ₂ CH ₂ OMe H 4-191 2-Me, 4-Ph CH ₂ CH ₂ OMe COtBu 4-192 2-Me, 4-Ph CH ₂ CH ₂ OMe C (S) SEt 4-193 2,6-Me ₂ ,, 4-Ph H COtBu 4-194 2,6 -Me ₂ , 4-Ph Me H 4-195 2,6-Me ₂ , 4-Ph Me COtBu 4-196 2,6-Me ₂ , 4-Ph Me C (S) SEt 4-197 2,6- Me ₂ , 4-Ph Et H 4-198 2,6-Me ₂ , 4-Ph Et COtBu 4-199 2,6-Me ₂ , 4-Ph Et C (S) SEt 4-200 2,6-Me _{2, 4-Ph CH 2 OMe} H 4-201 2,6-Me 2, 4-Ph CH 2 OMe COtBu 4-202 2,6-Me 2, 4-Ph CH 2 OMe C (S) SEt 4-203 2,6-Me ₂ , 4-Ph CH ₂ OEt H 4-204 2,6-Me ₂ , 4-Ph CH ₂ OEt COtBu 4-205 2,6-Me ₂ , 4-Ph CH ₂ OEt C (S) SEt 4-206 2,6-Me ₂ , 4-Ph CH _{2 CH 2 OMe H 4-207 2,6-Me} 2, 4-Ph CH 2 CH 2 OMe COtBu 4-208 2,6-Me 2, 4-Ph CH 2 CH 2 OMe C (S) SEt 4-209 2 , 6-Me ₂ , 4-CN H COtBu 4-210 2,6-Me ₂ , 4-CN Me H 4-211 2,6-Me ₂ , 4-CN Me COtBu 4-212 2,6-Me ₂ , 4-CN Me C (S) SEt 4-213 2,6-Me ₂ , 4-CN Et H 4-214 2,6-Me ₂ , 4-CN Et COtBu 4-215 2,6-Me ₂ , 4-CN Et C (S) SEt 4-216 2,6-Me ₂ , 4-CN CH ₂ OMe H 4-217 2,6-Me ₂ , 4-CN CH ₂ OMe COtBu 4-218 2,6- _{Me 2, 4-CN CH 2} OMe C (S) SEt 4-219 2,6-Me 2, 4-CN CH 2 OEt H 4-220 2,6-Me 2, 4-CN CH 2 OEt COtBu 4- 221 2,6-Me ₂ , 4-CN CH ₂ OEt C (S) SEt 4-222 2,6-Me ₂ , 4-CN CH ₂ CH ₂ OMe H 4-223 2,6-Me ₂ , 4- CN CH ₂ CH ₂ OMe COtBu 4-224 2,6-Me ₂ ,, 4-CN CH ₂ CH ₂ OMe C (S) SEt 4-225 2,3,6-Me ₃ H COtBu 4-226 2,3, 6-Me ₃ Me H 4-227 2,3,6-Me ₃ Me COtBu 4-228 2,3,6-Me ₃ Me C (S) SEt 4-229 2,3,6-Me ₃ Et H 4 -230 2,3,6-Me ₃ Et COtBu 4-231 2,3,6-Me ₃ Et C (S) SEt 4-232 2,3,6-Me ₃ CH ₂ OMe H 4-233 2,3 , 6-Me ₃ CH ₂ OMe COtBu 4-234 2,3,6-Me ₃ CH ₂ OMe C (S) SEt 4 -235 2,3,6-Me ₃ CH ₂ OEt H 4-236 2,3,6-Me ₃ CH ₂ OEt COtBu 4-237 2,3,6-Me ₃ CH ₂ OEt C (S) SEt 4- 238 2,3,6-Me ₃ CH ₂ CH ₂ OMe H 4-239 2,3,6-Me ₃ CH ₂ CH ₂ OMe COtBu 4-240 2,3,6-Me ₃ CH ₂ CH ₂ OMe C ( S) SEt 4-241 2,3,4,6-Me ₄ H COtBu 4-242 2,3,4,6-Me ₄ Me H 4-243 2,3,4,6-Me ₄ Me COtBu 4- 244 2,3,4,6-Me ₄ Me C (S) SEt 4-245 2,3,4,6-Me ₄ Et H 4-246 2,3,4,6-Me ₄ Et COtBu 4-247 2,3,4,6-Me ₄ Et C (S) SEt 4-248 2,3,4,6-Me ₄ CH ₂ OMe H 4-249 2,3,4,6-Me ₄ CH ₂ OMe COtBu 4-250 2,3,4,6-Me ₄ CH ₂ OMe C (S) SEt 4-251 2,3,4,6-Me ₄ CH ₂ OEt H 4-252 2,3,4,6-Me ₄ CH ₂ OEt COtBu 4-253 2,3,4,6-Me ₄ CH ₂ OEt C (S) SEt 4-254 2,3,4,6-Me ₄ CH ₂ CH ₂ OMe H 4-255 2, 3,4,6-Me ₄ CH ₂ CH ₂ OMe COtBu 4-256 2,3,4,6-Me ₄ CH ₂ CH ₂ OMe C (S) SEt 4-257 2,4,6-Me ₃ , 3 -Cl H COtBu 4-258 2,4,6-Me ₃ , 3-Cl Me H 4-259 2,4,6-Me ₃ , 3-Cl Me COtBu 4-260 2,4,6-Me ₃ , 3-Cl Me C (S) SEt 4-261 2,4,6-Me ₃ , 3-Cl Et H 4-262 2,4,6-Me ₃ , 3-Cl Et COtBu 4-263 2,4, 6-Me ₃ , 3-Cl Et C (S) SEt 4-264 2,4,6-Me ₃ , 3-Cl CH ₂ OMe H 4-265 2,4,6-Me ₃ , 3-Cl CH ₂ OMe COtBu 4 -266 2,4,6-Me ₃ , 3-Cl CH ₂ OMe C (S) SEt 4-267 2,4,6-Me ₃ , 3-Cl CH ₂ OEt H 4-268 2,4,6- Me ₃ , 3-Cl CH ₂ OEt COtBu 4-269 2,4,6-Me ₃ , 3-Cl CH ₂ OEt C (S) SEt 4-270 2,4,6-Me ₃ , 3-Cl CH ₂ CH ₂ OMe H 4-271 2,4,6-Me ₃ , 3-Cl CH ₂ CH ₂ OMe COtBu 4-272 2,4,6-Me ₃ , 3-Cl CH ₂ CH ₂ OMe C (S) SEt 4-273 2,6-Cl ₂ H COtBu 4-274 2,6-Cl ₂ Me H 4-275 2,6-Cl ₂ Me COtBu 4-276 2,6-Cl ₂ Me C (S) SEt 4- 277 2,6-Cl ₂ Et H 4-278 2,6-Cl ₂ Et COtBu 4-279 2,6-Cl ₂ Et COCH ₂ tBu 4-280 2,6-Cl ₂ Et C (S) SEt 4- 281 2,6-Cl ₂ CH ₂ OMe H 4-282 2,6-Cl ₂ CH ₂ OMe COtBu 4-283 2,6-Cl ₂ CH ₂ OMe C (S) SEt 4-284 2,6-Cl ₂ CH ₂ OEt H 4-285 2,6-Cl ₂ CH ₂ OEt COtBu 4-286 2,6-Cl ₂ CH ₂ OEt C (S) SEt 4-287 2,6-Cl ₂ CH ₂ CH ₂ OMe H 4 -288 2,6-Cl ₂ CH ₂ CH ₂ OMe COtBu 4-289 2,6-Cl ₂ CH ₂ CH ₂ OMe C (S) SEt 4-290 2,5-Cl ₂ H COtBu 4-291 2,5 -Cl ₂ Me H 4-292 2,5-Cl ₂ Me COtBu 4-293 2,5-Cl ₂ Me C (S) SEt 4-294 2,5-Cl ₂ Et H 4-295 2,5-Cl ₂ Et COtBu 4-296 2,5-Cl ₂ Et C (S) SEt 4-297 2,5-Cl ₂ CH ₂ OMe H 4-298 2,5-Cl ₂ CH ₂ OMe COtBu 4-299 2,5 -Cl ₂ CH ₂ OMe C (S) SEt 4-300 2,5-Cl ₂ CH ₂ OEt H 4-301 2,5-Cl ₂ CH ₂ OEt COtBu 4-302 2,5-Cl ₂ CH ₂ OEt C (S) SEt 4-303 2,5- Cl ₂ CH ₂ CH ₂ OMe H 4-305 2,5-Cl ₂ CH ₂ CH ₂ OMe C (S) SEt 4-306 3,5-Cl ₂ H COtBu 4-307 3,5-Cl ₂ Me H 4 -308 3,5-Cl ₂ Me COtBu 4-309 3,5-Cl ₂ Me C (S) SEt 4-310 3,5-Cl ₂ Et H 4-311 3,5-Cl ₂ Et COtBu 4-312 3,5-Cl ₂ Et C (S) SEt 4-313 3,5-Cl ₂ CH ₂ OMe H 4-314 3,5-Cl ₂ CH ₂ OMe COtBu 4-315 3,5-Cl ₂ CH ₂ OMe C (S) SEt 4-316 3,5-Cl ₂ CH ₂ OEt H 4-317 3,5-Cl ₂ CH ₂ OEt COtBu 4-318 3,5-Cl ₂ CH ₂ OEt C (S) SEt 4- 319 3,5-Cl ₂ CH ₂ CH ₂ OMe H 4-320 3,5-Cl ₂ CH ₂ CH ₂ OMe COtBu 4-321 3,5-Cl ₂ CH ₂ CH ₂ OMe C (S) SEt 4-322 2-Cl, 6-Br H COtBu 4-323 2-Cl, 6-Br Me H 4-324 2-Cl, 6-Br Me COtBu 4-325 2-Cl, 6-Br Me C (S) SEt 4 -326 2-Cl, 6-Br Et H 4-327 2-Cl, 6-Br Et COtBu 4-328 2-Cl, 6-Br Et C (S) SEt 4-329 2-Cl, 6-Br CH ₂ OMe H 4-330 2-Cl, 6-Br CH ₂ OMe COtBu 4-331 2-Cl, 6-Br CH ₂ OMe C (S) SEt 4-332 2-Cl, 6-Br CH ₂ OEt H 4 -333 2-Cl, 6-Br CH ₂ OEt COtBu 4-334 2-Cl, 6-Br CH ₂ OEt C (S) SEt 4-335 2-Cl, 6-Br CH ₂ CH ₂ OMe H 4-336 2-Cl, 6-Br CH ₂ CH ₂ OMe COtBu 4-337 2-Cl, 6-Br CH ₂ CH ₂ OMe C (S) SEt 4-338 2-Br H COtBu 4-339 2-Br Me H 4-340 2-Br Me COtBu 4-341 2-Br Me C (S) SEt 4-342 2-Br Et H 4-343 2-Br Et COtBu 4-344 2-Br Et C (S) SEt 4-345 2-Br CH ₂ OMe H 4-346 2-Br CH ₂ OMe COtBu 4-347 2-Br CH ₂ OMe C (S) SEt 4-348 2-Br CH ₂ OEt H 4-349 2-Br CH ₂ OEt COtBu 4-350 2-Br CH ₂ OEt C (S) SEt 4-351 2-Br CH ₂ CH ₂ OMe H 4-352 2-Br CH ₂ CH ₂ OMe COtBu 4-353 2-Br CH ₂ CH ₂ OMe C (S) SEt 4- 354 2-Br, 4-Me H COtBu 4-355 2-Br, 4-Me Me H 4-356 2-Br, 4-Me Me COtBu 4-357 2-Br, 4-Me Me C (S) SEt 4-358 2-Br, 4-Me Et H 4-359 2-Br, 4-Me Et COtBu 4-360 2-Br, 4-Me Et C (S) SEt 4-361 2-Br, 4-Me CH ₂ OMe H 4-362 2-Br, 4-Me CH ₂ OMe COtBu 4-363 2-Br, 4-Me CH ₂ OMe C (S) SEt 4-364 2-Br, 4-Me CH ₂ OEt H 4-365 2-Br, 4-Me CH ₂ OEt COtBu 4-366 2-Br, 4-Me CH ₂ OEt C (S) SEt 4-367 2-Br, 4-Me CH ₂ CH ₂ OMe H 4- 368 2-Br, 4-Me CH ₂ CH ₂ OMe COtBu 4-369 2-Br, 4-Me CH ₂ CH ₂ OMe C (S) SEt 4-370 2,6-Cl ₂ , 4-CF ₃ H COtBu 4-371 2,6-Cl ₂ , 4-CF ₃ Me H 4-372 2,6-Cl ₂ , 4-CF ₃ Me COtBu 4-373 2,6-Cl ₂ , 4-CF ₃ Me C (S) SEt 4-374 2,6-Cl ₂ , 4-CF ₃ Et H 4-375 2,6-Cl ₂ , 4-CF ₃ Et COtBu 4-376 2,6- Cl ₂ , 4-CF ₃ Et C (S) SEt 4-377 2,6-Cl ₂ , 4-CF ₃ CH ₂ OMe H 4-378 2,6-Cl ₂ , 4-CF ₃ CH ₂ OMe COtBu 4 -379 2,6-Cl ₂ , 4-CF ₃ CH ₂ OMe C (S) SEt 4-380 2,6-Cl ₂ , 4-CF ₃ CH ₂ OEt H 4-381 2,6-Cl ₂ , 4 -CF ₃ CH ₂ OEt COtBu 4-382 2,6-Cl ₂ , 4-CF ₃ CH ₂ OEt C (S) SEt 4-383 2,6-Cl ₂ , 4-CF ₃ CH ₂ CH ₂ OMe H 4 -384 2,6-Cl ₂ , 4-CF ₃ CH ₂ CH ₂ OMe COtBu 4-385 2,6-Cl ₂ , 4-CF ₃ CH ₂ CH ₂ OMe C (S) SEt 4-386 2,4, 6-Me ₃ H COtBu 4-387 2,4,6-Me ₃ Et H 4-388 2,4,6-Me ₃ Et COtBu 4-389 2,4,6-Me ₃ Et C (S) SEt 4 -392 2,4,6-Me ₃ CH ₂ OMe C (S) SEt 4-395 2,4,6-Me ₃ CH ₂ OEt C (S) SEt 4-396 2,4,6-Me ₃ CH ₂ CH ₂ OMe H 4-397 2,4,6-Me ₃ CH ₂ CH ₂ OMe COtBu 4-398 2,4,6-Me ₃ CH ₂ CH ₂ OMe C (S) SEt 4-399 2,4-Cl ₂ CH ₂ OMe COcPr 4-400 2,4-Cl ₂ Me COcPr 4-401 2,6-Me ₂ CH ₂ OEt CO (2-OMe-Ph) 4-402 2,6-Me ₂ CH ₂ OEt CO ( 2-Me-Ph) 4-403 2,6-Me ₂ Me COcPr 4-404 2,6-Me ₂ Me COcPr (1-Me) 4-405 2,6-Me ₂ CH ₂ OMe COcPr 4-406 2 , 6-Me ₂ CH ₂ OMe COcPr (1-Me) 4-407 2,6-M e ₂ CH ₂ OEt COcPr 4-408 2,6-Me ₂ CH ₂ OEt COcPr (1-Me) 4-409 2,6-Me ₂ CH ₂ OEt H 4-410 2,6-Me ₂ CH ₂ OEt COMe 4-411 2,6-Me ₂ CH ₂ OEt COEt 4-412 2,6-Me ₂ CH ₂ OEt COiPr 4-413 2,6-Me ₂ CH ₂ OEt CO ₂ Et 4-414 2,6-Me ₂ CH ₂ CH ₂ OMe H 4-415 2,6-Me ₂ CH ₂ CH ₂ OMe COMe 4-416 2,6-Me ₂ CH ₂ CH ₂ OMe COEt 4-417 2,6-Me ₂ CH ₂ CH ₂ OMe COiPr 4-418 2,6-Me ₂ CH ₂ CH ₂ OMe COcPr 4-419 2,6-Me ₂ CH ₂ CH ₂ OMe CO ₂ Et ───────────────────

[0097]

[Table 5]

[0098]

Embedded image 化合物 Compound number R ¹ R ² R ³ R ⁴ ──── ──────────────────────────────── 5-1 Me Me Me H 5-2 Me Me Me Ac 5-3 Me Me Me COEt 5-4 Me Me Me COPr 5-5 Me Me Me COiPr 5-6 Me Me Me COBu 5-7 Me Me Me COtBu 5-8 Me Me Me COcHex 5-9 Me Me Me COPh 5-10 Me Me Me CO (2-Cl-Ph) 5-11 Me Me Me COCH = CH ₂ 5-12 Me Me Me COC (Me) = CH ₂ 5-13 Me Me Me COCH ₂ OMe 5-14 Me Me Me COCH ₂ OPh 5-15 Me Me Me COCH ₂ tBu 5-16 Me Me Me CO ₂ Me 5-17 Me Me Me CO ₂ Et 5-18 Me Me Me CO ₂ Pr 5-19 Me Me Me CO ₂ iPr 5-20 Me Me Me CO ₂ Bu 5-21 Et Me Me CO ₂ iBu 5-22 Me Me Me CO ₂ tBu 5-23 Me Me Me CO ₂ cPent 5-24 Me Me Me CO ₂ cHex 5-25 Me Me Me CO ₂ CH ₂ CH = CH ₂ 5-26 Me Me Me CO ₂ CH ₂ tBu 5-27 Me Me Me CO ₂ CH ₂ (2-Thf) 5-28 Me Me Me CO ₂ CH ₂ C (Me) ₂ CH ₂ Cl 5- 29 Me Me Me CO ₂ CH (Me) iPr 5-30 Me Me Me C (O) SMe 5-31 Me Me Me C (O) SEt 5-32 Me Me Me C (O) S-tBu 5- 33 Me Me Me C (O) SPh 5-34 Me Me Me C (S) OMe 5-35 Me Me Me C (S) OEt 5-36 Me Me Me C (S) OtBu 5-37 Me Me Me C ( S) OPh 5-38 Me Me Me C (S) SMe 5-39 Me Me Me C (S) SEt 5-40 Me Me Me C (S) SPr 5-41 Me Me Me C (S) S-iPr 5 -42 Me Me Me C (S) SBu 5-43 Me Me Me C (S) S-tBu 5-44 Me Me Me C (S) SCH ₂ tBu 5-45 Me Me Me C (S) SPh 5-46 Me Me Me Me 5-47 Me Me Me CH ₂ OMe 5-48 Me Me Me CH ₂ OPh 5-49 Me Me Me CH ₂ Ph 5-50 Me Me Me SO ₂ Me 5-51 Me Me Me SO ₂ Et 5 -52 Me Me Me SO ₂ Ph 5-53 Me Me Me SO ₂ Ph (4-Me) 5-54 Me Me Me P (S) (OMe) ₂ 5-55 Me Me Me P (S) (OEt) ₂ 5-56 Me Me Me Na 5-57 Me Me Me K 5-58 Me Me Me NH ₄ ⁺ 5-59 Me-(CH ₂ ) ₅ -H 5-60 Me-(CH ₂ ) ₅ -COtBu 5-61 Me-(CH ₂ ) ₅ -COCH ₂ tBu 5-62 Me-(CH ₂ ) ₅ -C (S) SEt 5-63 Me-(CH ₂ ) ₂ -CH (Me)-(CH ₂ ) ₂ -H 5-64 Me-(CH ₂ ) ₂ -CH (Me)-(CH ₂ ) ₂ -COtBu 5-65 Me-(CH ₂ ) ₂ -CH (Me)-(CH ₂ ) ₂ -COCH ₂ tBu 5- 66 Me-(CH ₂ ) ₂ -CH (Me)-(CH ₂ ) ₂ -C (S) SEt 5-67 Me-(CH ₂ ) ₂ -CH (OMe)-(CH ₂ ) ₂ -H 5- 68 Me-(CH ₂ ) ₂ -CH (OMe)-(CH ₂ ) ₂ -COtBu 5-69 Me-(CH ₂ ) ₂ -CH (OMe)-(CH ₂ ) ₂ -COCH ₂ tBu 5-70 Me-(CH ₂ ) ₂ -CH (OMe)-(CH ₂ ) ₂ -C (S) SEt 5-71 Me-(CH ₂ ) ₂ -O- (CH ₂ ) _2- H 5-72 Me-(CH ₂ ) ₂ -O- (CH ₂ ) ₂ -COtBu 5-73 Me-(CH ₂ ) ₂ -O- (CH ₂ ) ₂ -COCH ₂ tBu 5-74 Me-(CH ₂ ) ₂ -O- (CH ₂ ) ₂ -C (S) SEt 5-75 Me-(CH ₂ ) ₂ -S- (CH ₂ ) ₂ -H 5-76 Me-(CH ₂ ) ₂ -S- (CH ₂ ) ₂ -COtBu 5-77 Me-(CH ₂ ) ₂ -S- (CH ₂ ) ₂ -COCH ₂ tBu 5-78 Me-(CH ₂ ) ₂ -S- (CH ₂ ) ₂ -C ( S) SEt 5-79 Et Me Me H 5-80 Et Me Me Ac 5-81 Et Me Me COEt 5-82 Et Me Me COPr 5-83 Et Me Me COiPr 5-84 Et Me Me COBu 5-85 Et Me Me COtBu 5-86 Et Me Me COcHex 5-87 Et Me Me COPh 5-88 Et Me Me CO (2-Cl-Ph) 5-89 Et Me Me COCH = CH ₂ 5-90 Et Me Me COC (Me) = CH ₂ 5-91 Et Me Me COCH ₂ OMe 5-92 Et Me Me COCH ₂ OPh 5-93 Et Me Me COCH ₂ tBu 5-94 Et Me Me CO ₂ Me 5-95 Et Me Me CO ₂ Et 5- 96 Et Me Me CO ₂ Pr 5-97 Et Me Me CO ₂ iPr 5-98 Et Me Me CO ₂ Bu 5-99 Et Me Me CO ₂ iBu 5-100 Et Me Me CO ₂ tBu 5-101 Et Me Me CO ₂ cPent 5-102 Et Me Me CO ₂ cHex 5-103 Et Me Me CO ₂ CH ₂ CH = CH ₂ 5-104 Et Me Me CO ₂ CH ₂ tBu 5-105 Et Me Me CO ₂ CH ₂ (2-Thf) 5-106 Et Me Me CO ₂ CH ₂ C (Me) ₂ CH ₂ Cl 5-107 Et Me Me CO ₂ CH (Me) iPr 5-108 Et Me Me CO ₂ CH ₂ CH ₂ OiPr 5-109 Et Me Me CO ₂ CH (Me) iPr 5-110 Et Me Me CO ₂ C (Me) ₂ C≡CH 5-111 Et Me Me CO ₂ CH (Me) tBu 5-112 Et Me Me CO ₂ CH (iPr) ₂ 5-113 Et Me Me C (O) SMe 5-114 Et Me Me C (O) SEt 5-115 Et Me Me C (O) S-tBu 5-116 Et Me Me C (O ) SPh 5-117 Et Me Me C (S) OMe 5-118 Et Me Me C (S) OEt 5-119 Et Me Me C (S) OtBu 5-120 Et Me Me C (S) OPh 5-121 Et Me Me C (S) SMe 5-122 Et Me Me C (S) SEt 5-123 Et Me Me C (S) SPr 5-124 Et Me Me C (S) S-iPr 5-125 Et Me Me C ( S) SBu 5-126 Et Me Me C (S) S-tBu 5-127 Et Me Me C (S) SCH ₂ tBu 5-128 Et Me Me C (S) SPh 5-129 Et Me Me Me 5-130 Et Me Me CH ₂ OMe 5-131 Et Me Me CH ₂ OPh 5-132 Et Me Me CH ₂ Ph 5-133 Et Me Me SO ₂ Me 5-134 Et Me Me SO ₂ Et 5-135 Et Me Me SO _{2 Ph 5-136 Et Me Me SO 2 (} 4-Me-Ph) 5-137 Et Me Me P (S) (OMe) 2 5-138 Et Me Me P (S) (OEt) 2 5-139 Et Me Me Na 5-140 Et Me Me K 5-141 Et Me Me NH ₄ ⁺ 5-142 Et-(CH ₂ ) ₅ -H 5-143 Et-(CH ₂ ) ₅ -COtBu 5-144 Et-(CH ₂ ) ₅ -CO CH ₂ tBu 5-145 Et-(CH ₂ ) ₅ -C (S) SEt 5-146 Et-(CH ₂ ) ₂ -CH (Me)-(CH ₂ ) ₂ -H 5-147 Et-(CH ₂ ) ₂ -CH (Me)-(CH ₂ ) ₂ -COtBu 5-148 Et-(CH ₂ ) ₂ -CH (Me)-(CH ₂ ) ₂ -COCH ₂ tBu 5-149 Et-(CH ₂ ) ₂ -CH (Me)-(CH ₂ ) ₂ -C (S) SEt 5-150 Et-(CH ₂ ) ₂ -CH (OMe)-(CH ₂ ) ₂ -H 5-151 Et-(CH ₂ ) ₂ -CH (OMe)-(CH ₂ ) ₂ -COtBu 5-152 Et-(CH ₂ ) ₂ -CH (OMe)-(CH ₂ ) ₂ -COCH ₂ tBu 5-153 Et-(CH ₂ ) ₂ -CH (OMe)-(CH ₂ ) ₂ -C (S) SEt 5-154 Et-(CH ₂ ) ₂ -O- (CH ₂ ) ₂ -H 5-155 Et-(CH ₂ ) ₂ -O- (CH ₂ ) ₂ -COtBu 5-156 Et-(CH ₂ ) ₂ -O- (CH ₂ ) ₂ -COCH ₂ tBu 5-157 Et-(CH ₂ ) ₂ -O- (CH ₂ ) ₂ -C (S) SEt 5-158 Et-(CH ₂ ) ₂ -S- (CH ₂ ) ₂ -H 5-159 Et-(CH ₂ ) ₂ -S- (CH ₂ ) ₂ -COtBu 5-160 Et-(CH ₂ ) ₂ -S- (CH ₂ ) ₂ -COCH ₂ tBu 5-161 Et-(CH ₂ ) ₂ -S- (CH ₂ ) ₂ -C (S) SEt 5-162 Pr Me Me H 5-163 Pr Me Me COtBu 5-164 Pr Me Me COCH ₂ tBu 5-165 Pr Me Me CO (S) SEt 5-166 iPr Me Me H 5-167 iPr Me Me COtBu 5-168 iPr Me Me COCH ₂ tBu 5-169 iPr Me Me CO (S) SEt 5-170 Bu Me Me H 5-171 Bu Me Me COtBu 5-172 Bu Me Me COCH ₂ tBu 5-173 Bu Me Me CO (S) SEt 5-174 iBu Me Me H 5-175 iBu Me Me COtBu 5-176 iBu Me Me COCH ₂ tBu 5-177 iBu Me Me CO (S) SEt 5-178 tBu Me Me H 5 -179 tBu Me Me COtBu 5-180 tBu Me Me COCH ₂ tBu 5-181 tBu Me Me CO (S) SEt 5-182 CH ₂ Ph Me Me H 5-183 CH ₂ Ph Me Me COtBu 5-184 CH ₂ Ph Me Me COCH ₂ tBu 5-185 CH ₂ Ph Me Me CO (S) SEt 5-186 Ph Me Me H 5-187 Ph Me Me COtBu 5-188 Ph Me Me COCH ₂ tBu 5-189 Ph Me Me CO (S ) SEt 5-190 Me Me Me COcPr ────────────────────────────────────

[0099]

[Table 6]

[0100]

Embedded image ──────────────────────────────────── Compound number (A) _n R ¹ R ⁴ ──── ──────────────────────────────── 6-1 2-Cl Me H 6-2 2-Cl Me COtBu 6- 3 2-Cl Me COCH ₂ tBu 6-4 2-Cl Me C (S) SEt 6-5 2-CF ₃ Me H 6-6 2-CF ₃ Me COtBu 6-7 2-CF ₃ Me COCH ₂ tBu 6 -8 2-CF ₃ Me C (S) SEt 6-9 2-Cl, 4-Me Me H 6-10 2-Cl, 4-Me Me COtBu 6-11 2-Cl, 4-Me Me COCH ₂ tBu 6-12 2-Cl, 4-Me Me C (S) SEt 6-13 2-Cl, 4-Me Et H 6-14 2-Cl, 4-Me Et COtBu 6-15 2-Cl, 4-Me Et COCH ₂ tBu 6-16 2-Cl, 4-Me Et C (S) SEt 6-17 2-Cl, 4-Me Pr H 6-18 2-Cl, 4-Me Pr COtBu 6-19 2-Cl , 4-Me Pr COCH ₂ tBu 6-20 2-Cl, 4-Me Pr C (S) SEt 6-21 2-Cl, 4-Me iPr H 6-22 2-Cl, 4-Me iPr COtBu 6- 23 2-Cl, 4-Me iPr COCH ₂ tBu 6-24 2-Cl, 4-Me iPr C (S) SEt 6-25 2,4-Cl ₂ Me H 6-26 2,4-Cl ₂ Me COtBu 6-27 2,4-Cl ₂ Me COCH ₂ tBu 6-28 2,4-Cl ₂ Me C (S) SEt 6-29 2,4-Cl ₂ Et H 6-30 2,4-Cl ₂ Et COtBu 6-31 2,4-Cl ₂ Et COCH ₂ tBu 6-32 2,4-Cl ₂ Et C (S) SEt 6-33 2-Br, 4-Me Me H 6-34 2-Br, 4-Me Me COtBu 6-35 2-Br, 4-Me Me COCH ₂ tBu 6-36 2-Br, 4-Me Me C (S) SEt 6-37 2-Me, 4-OMe Me H 6-38 2-Me, 4-OMe Me COtBu 6-39 2-Me, 4-OMe Me COCH ₂ tBu 6-40 2-Me, 4-OMe Me C (S) SEt 6-41 2- Cl Et C (S) SEt 6-42 2-Cl Me CO (2-Cl-Ph) 6-43 2-Cl Me P (S) (OEt) 2 6-44 2-Cl tBu C (S) SEt 6-45 2,4-Cl ₂ Me COcPr 6-46 2,6-Me ₂ Me COcPr ─────────────────── ─────────────────

[0101]

[Table 7]

[0102]

Embedded image ──────────────────────────────────── Compound number (A) _n R ¹ m R ⁴ ─── ───────────────────────────────── 7-1 2,4,6-Me ₃ Me 1 H 7-2 2,4,6-Me ₃ Me 1 COtBu 7-3 2,4,6-Me ₃ Me 1 COCH ₂ tBu 7-4 2,4,6-Me ₃ Me 1 CO ₂ Me 7-5 2,4, 6-Me ₃ Me 1 CO ₂ CH ₂ tBu 7-6 2,4,6-Me ₃ Me 1 CO ₂ CH ₂ C (Me) ₂ CH ₂ Cl 7-7 2,4,6-Me ₃ Me 1 C (S) SEt 7-8 2,4,6-Me ₃ Me 1 C (S) SPr 7-9 2,4,6-Me ₃ Me 2 H 7-10 2,4,6-Me ₃ Me 2 COtBu 7-11 2,4,6-Me ₃ Me 2 COCH ₂ tBu 7-12 2,4,6-Me ₃ Me 2 CO ₂ Me 7-13 2,4,6-Me ₃ Me 2 CO ₂ CH ₂ tBu 7-14 2,4,6-Me ₃ Me 2 CO ₂ CH ₂ C (Me) ₂ CH ₂ Cl 7-15 2,4,6-Me ₃ Me 2 C (S) SEt 7-16 2,4, 6-Me ₃ Me 2 C (S) SPr 7-17 2,4,6-Me ₃ Et 1 H 7-18 2,4,6-Me ₃ Et 1 COtBu 7-19 2,4,6-Me ₃ Et 1 COCH ₂ tBu 7-20 2,4,6-Me ₃ Et 1 CO ₂ Me 7-21 2,4,6-Me ₃ Et 1 CO ₂ CH ₂ tBu 7-22 2,4,6-Me ₃ Et 1 CO ₂ CH ₂ C (Me) ₂ CH ₂ Cl 7-23 2,4,6-Me ₃ Et 1 C (S) SEt 7-24 2,4,6-Me ₃ Et 1 C (S) SPr 7-25 2 , 4,6-Me ₃ Et 2 H 7-26 2,4,6-Me ₃ Et 2 COtBu 7-27 2,4,6-Me ₃ Et 2 COCH ₂ tBu 7-28 2,4,6-Me ₃ Et 2 CO ₂ Me 7-29 2,4,6-Me ₃ Et 2 CO ₂ CH ₂ tBu 7-30 2,4,6-Me ₃ Et 2 CO ₂ CH ₂ C (Me) ₂ CH ₂ Cl 7 -31 2,4,6-Me ₃ Et 2 C (S) SEt 7-32 2,4,6-Me ₃ Et 2 C (S) SPr ─────────────── ─────────────────────

[0103]

[Table 8]

[0104]

Embedded image ──────────────────────────────────── Compound number (A) _n R ¹ R ² R ³ R ⁵ ──────────────────────────────────── 8-1 2,4,6-Me ₃ HHH Me 8 -2 2,4,6-Me ₃ HMe H Me 8-3 2,4,6-Me ₃ H Me Me Me 8-4 2,4,6-Me ₃ H Me Et Me 8-5 2,4 , 6-Me ₃ H Me iPr Me 8-6 2,4,6-Me ₃ H Me CH ₂ Ph Me 8-7 2,4,6-Me ₃ H-(CH ₂ ) ₅ -Me 8-8 2 _{, 4,6-Me 3 H - (} CH 2) 2 -CHMe- (CH 2) 2 - Me 8-9 2,4,6-Me 3 H - (CH 2) 2 -CH (OMe) - (CH ₂ ) ₂ -Me 8-10 2,4,6-Me ₃ H-(CH ₂ ) ₂ -O- (CH ₂ ) ₂ -Me 8-11 2,4,6-Me ₃ HHH Et 8-12 2 , 4,6-Me ₃ H Me H Et 8-13 2,4,6-Me ₃ H Me Me Et 8-14 2,4,6-Me ₃ H Me Et Et 8-15 2,4,6- Me ₃ H Me iPr Et 8-16 2,4,6-Me ₃ H Me CH ₂ Ph Et 8-17 2,4,6-Me ₃ H-(CH ₂ ) ₅ -Et 8-18 2,4, _{6-Me 3 H - (CH} 2) 2 -CHMe- (CH 2) 2 - Et 8-19 2,4,6-Me 3 H - (CH 2) 2 -CH (OMe) - (CH 2) 2 -Et 8-20 2,4,6-Me ₃ H-(CH ₂ ) ₂ -O- (CH ₂ ) ₂ -Et 8-21 2,4,6-Me ₃ Me HH Me 8-22 2,4 , 6-Me ₃ Me Me H Me 8-23 2, 4,6-Me ₃ Me Me Me Me 8-24 2,4,6-Me ₃ Me Me Et Me 8-25 2,4,6-Me ₃ Me Me iPr Me 8-26 2,4,6-Me ₃ Me Me CH ₂ Ph Me 8-27 2,4,6-Me ₃ Me-(CH ₂ ) ₅ -Me 8-28 2,4,6-Me ₃ Me-(CH ₂ ) ₂ -CHMe- (CH ₂ ) ₂ -Me 8-29 2,4,6-Me ₃ Me-(CH ₂ ) ₂ -CH (OMe)-(CH ₂ ) ₂ -Me 8-30 2,4,6-Me ₃ Me-( CH ₂ ) ₂ -O- (CH ₂ ) ₂ -Me 8-31 2,4,6-Me ₃ Me HH Et 8-32 2,4,6-Me ₃ Me Me H Et 8-33 2,4, 6-Me ₃ Me Me Me Et 8-34 2,4,6-Me ₃ Me Me Et Et 8-35 2,4,6-Me ₃ Me Me iPr Et 8-36 2,4,6-Me ₃ Me _{Me CH 2 Ph Et 8-37 2,4,6-} Me 3 Me - (CH 2) 5 - Et 8-38 2,4,6-Me 3 Me - (CH 2) 2 -CHMe- (CH 2) ₂ -Et 8-39 2,4,6-Me ₃ Me-(CH ₂ ) ₂ -CH (OMe)-(CH ₂ ) ₂ -Et 8-40 2,4,6-Me ₃ Me-(CH ₂ ) ₂ -O- (CH ₂ ) ₂ -Et 8-41 2,4,6-Me ₃ Et Me Me Et 8-42 2,4,6-Me ₃ Pr Me Me Et 8-43 2,4,6 -Me ₃ iPr Me Me Et 8-44 2,4,6-Me ₃ CH ₂ CH = CH ₂ Me Me Et 8-45 2,4,6-Me ₃ CH ₂ C≡CH Me Me Et 8-46 2 , 4,6-Me ₃ CH ₂ Ph Me Me Et 8-47 2,4,6-Me ₃ CH ₂ cHex Me Me Et 8-48 2,4,6-Me ₃ CH ₂ OMe Me Me Et 8-49 2,4,6-Me ₃ CH ₂ OEt Me Me Et 8-50 2,4,6-Me ₃ CH ₂ CH ₂ OMe Me Me Et 8-51 2,4 , 6-Me ₃ CH ₂ O (CH ₂ ) ₂ OMe Me Me Et 8-52 2,4,6-Me ₃ CH ₂ SMe Me Me Et 8-53 2,4,6-Me ₃ CH ₂ CH (OMe ) ₂ Me Me Et 8-54 2,4,6-Me ₃ CH ₂ (2-Diox) Me Me Et 8-55 2,4,6-Me ₃ CH ₂ (2-Thf) Me Me Et 8-56 2,4,6-Me ₃ CH ₂ (2-Pyr) Me Me Et 8-57 2,4,6-Me ₃ CH ₂ (3-Pyr) Me Me Et 8-58 2,4,6-Me ₃ CH ₂ OCH ₂ Ph Me Me Et 8-59 2,4,6-Me ₃ CH ₂ CH = CHCl Me Me Et 8-60 2,4-Cl ₂ H Me Me Et 8-61 2,4-Cl ₂ Me Me Me Et 8-62 2,4-Cl ₂ CH ₂ OMe Me Me Et 8-63 2,4-Cl ₂ CH ₂ OEt Me Me Et 8-64 2,4-Cl ₂ CH ₂ CH ₂ OMe Me Me Et 8-65 2-Cl, 4-Me H Me Me Et 8-66 2-Cl, 4-Me Me Me Me 8-67 2-Cl, 4-Me CH ₂ OMe Me Me 8-68 2-Cl , 4-Me CH ₂ OEt Me Me Et 8-69 2-Cl, 4-Me CH ₂ CH ₂ OMe Me Me Et 8-70 2,6-Me ₂ , 4-Br H Me Me Et 8-71 2, 6-Me ₂ ,, 4-Br Me Me Me Et 8-72 2,6-Me ₂ ,, 4-Br CH ₂ OMe Me Me Et 8-73 2,6-Me ₂ ,, 4-Br CH ₂ OEt Me Me Et 8-74 2,6-Me ₂ , 4-Br CH ₂ CH ₂ OMe Me Me Et 8-75 2,3-Me ₂ H Me Me Et 8-76 2,3-Me ₂ Me Me Me Et 8-77 2,3-Me ₂ CH ₂ OMe Me Me Et 8-78 2,3-Me ₂ CH ₂ OEt Me Me Et 8-79 2,3-Me ₂ CH ₂ CH ₂ OMe Me Me Et 8-80 2,4 -Me ₂ H Me Me Et 8-81 2,4-Me ₂ Me Me Me Et 8-82 2,4-Me ₂ CH ₂ OMe Me Me Et 8-83 2,4-Me ₂ CH ₂ OEt Me Me Et 8-84 2 _{, 4-Me 2 CH 2 CH} 2 OMe Me Me Et 8-85 2,5-Me 2 H Me Me Et 8-86 2,5-Me 2 Me Me Me Et 8-87 2,5-Me 2 CH 2 OMe Me Me Et 8-88 2,5-Me ₂ CH ₂ OEt Me Me Et 8-89 2,5-Me ₂ CH ₂ CH ₂ OMe Me Me Et 8-90 2,6-Me ₂ H Me Me Et 8 -91 2,6-Me ₂ Me Me Me Et 8-92 2,6-Me ₂ CH ₂ OMe Me Me Et 8-93 2,6-Me ₂ CH ₂ OEt Me Me Et 8-94 2,6-Me ₂ CH ₂ CH ₂ OMe Me Me Et 8-95 2-Me, 4-Br H Me Me Et 8-96 2-Me, 4-Br Me Me Me Et 8-97 2-Me, 4-Br CH ₂ OMe Me Me Et 8-98 2-Me, 4-Br CH ₂ OEt Me Me Et 8-99 2-Me, 4-Br CH ₂ CH ₂ OMe Me Me Et 8-100 2-Me, 4-OMe H Me Me Et 8-101 2-Me, 4-OMe Me Me Me Et 8-102 2-Me, 4-OMe CH ₂ OMe Me Me Et 8-103 2-Me, 4-OMe CH ₂ OEt Me Me Et 8-104 2-Me, 4-OMe CH ₂ CH ₂ OMe Me Me Et 8-105 2-Me, 4-Ph H Me Me Et 8-106 2-Me, 4-Ph Me Me Me Et 8-107 2-Me, 4-Ph CH ₂ OMe Me Me Et 8-108 2-Me, 4-Ph CH ₂ OEt Me Me Et 8-109 2-Me, 4-Ph CH ₂ CH ₂ OMe Me Me Et 8-110 2,6- Me ₂ ,, 4-Ph H Me Me Et 8-111 2,6-Me ₂ ,, 4-Ph Me Me Me Et 8-112 2,6 -Me ₂ ,, 4-Ph CH ₂ OMe Me Me Et 8-113 2,6-Me ₂ ,, 4-Ph CH ₂ OEt Me Me Et 8-114 2,6-Me ₂ ,, 4-Ph CH ₂ CH ₂ OMe Me Me Et 8-115 2,6-Me ₂ ,, 4-CN H Me Me Et 8-116 2,6-Me ₂ ,, 4-CN Me Me Me Et 8-117 2,6-Me ₂ ,, 4-CN CH ₂ OMe Me Me Et 8-118 2,6-Me ₂ ,, 4-CN CH ₂ OEt Me Me Et 8-119 2,6-Me ₂ ,, 4-CN CH ₂ CH ₂ OMe Me Me Et 8-120 2 , 3,6-Me ₃ H Me Me Et 8-121 2,3,6-Me ₃ Me Me Me Et 8-122 2,3,6-Me ₃ CH ₂ OMe Me Me Et 8-123 2,3, 6-Me ₃ CH ₂ OEt Me Me Et 8-124 2,3,6-Me ₃ CH ₂ CH ₂ OMe Me Me Et 8-125 2,3,4,6-Me ₄ H Me Me Et 8-126 2 , 3,4,6-Me ₄ Me Me Me Et 8-127 2,3,4,6-Me ₄ CH ₂ OMe Me Me Me 8-128 2,3,4,6-Me ₄ CH ₂ OEt Me Me Et 8-129 2,3,4,6-Me ₄ CH ₂ CH ₂ OMe Me Me Et 8-130 2,4,6-Me ₃ , 4-Cl H Me Me Et 8-131 2,4,6- Me ₃ , 4-Cl Me Me Me Et 8-132 2,4,6-Me ₃ ,, 4-Cl CH ₂ OMe Me Me Et 8-133 2,4,6-Me ₃ ,, 4-Cl CH ₂ OEt Me Me Et 8-134 2,4,6-Me ₃ ,, 4-Cl CH ₂ CH ₂ OMe Me Me Et 8-135 2,6-Cl ₂ H Me Me Et 8-136 2,6-Cl ₂ Me Me Me Et 8-137 2,6-Cl ₂ CH ₂ OMe Me Me Et 8-138 2,6-Cl ₂ CH ₂ OEt Me Me Et 8-139 2,6-Cl ₂ CH ₂ CH ₂ OMe Me Me 8- 140 2,5-Cl ₂ H Me Me Et 8-141 2,5-Cl ₂ Me Me Me Et 8-142 2,5-Cl ₂ CH ₂ OMe Me Me Et 8-143 2,5-Cl ₂ CH ₂ OEt Me Me Et 8-144 2,5-Cl ₂ CH ₂ CH ₂ OMe Me Me Et 8-146 3,5-Cl ₂ Me Me Me Et 8-147 3,5-Cl ₂ CH ₂ OMe Me Me Et 8 -148 3,5-Cl ₂ CH ₂ OEt Me Me Et 8-149 3,5-Cl ₂ CH ₂ CH ₂ OMe Me Me Et 8-150 2-Cl, 6-Br H Me Me Et 8-151 2- Cl, 6-Br Me Me Me Et 8-152 2-Cl, 6-Br CH ₂ OMe Me Me Et 8-153 2-Cl, 6-Br CH ₂ OEt Me Me Et 8-154 2-Cl, 6- Br CH ₂ CH ₂ OMe Me Me Et 8-155 2-Br H Me Me Et 8-156 2-Br Me Me Me Et 8-157 2-Br CH ₂ OMe Me Me Et 8-158 2-Br CH ₂ OEt Me Me Et 8-159 2-Br CH ₂ CH ₂ OMe Me Me Et 8-160 2-Br, 4-Me H Me Me Et 8-161 2-Br, 4-Me Me Me Me Et 8-162 2- Br, 4-Me CH ₂ OMe Me Me Et 8-163 2-Br, 4-Me CH ₂ OEt Me Me Et 8-164 2-Br, 4-Me CH ₂ CH ₂ OMe Me Me Et 8-165 2, 6-Cl ₂ , 4-CF ₃ H Me Me Et 8-166 2,6-Cl ₂ , 4-CF ₃ Me Me Me Et 8-167 2,6-Cl ₂ , 4-CF ₃ CH ₂ OMe Me Me Et 8-168 2,6-Cl ₂ , 4-CF ₃ CH ₂ OEt Me Me Et 8-169 2,6-Cl ₂ , 4-CF ₃ CH ₂ CH ₂ OMe Me Me Et 8-170 2-Cl H Me Me Et 8-171 2-Cl Me Me Me Et 8-172 2 -Cl CH ₂ OMe Me Me Et 8-173 2-Cl CH ₂ OEt Me Me Et 8-174 2-Cl CH ₂ CH ₂ OMe Me Me Et ──────────────── ────────────────────

[0105]

[Table 9]

[0106]

Embedded image ──────────────────────────────────── Compound number (A) _n R ¹ R ² R ³ ── ────────────────────────────────── 9-1 2,4,6-Me ₃ H Me Me 9- _{2 2,4,6-Me 3 H - (} CH 2) 5 - 9-3 2,4,6-Me 3 H - (CH 2) 2 -CHMe- (CH 2) 2 - 9-4 2,4 _{, 6-Me 3 H - (} CH 2) 2 -CH (OMe) - (CH 2) 2 - 9-5 2,6-Me 2 H Me Me 9-6 2,6-Me 2 H - (CH 2 _{) 5 - 9-7 2,6-Me 2} H - (CH 2) 2 -CHMe- (CH 2) 2 - 9-8 2,6-Me 2 H - (CH 2) 2 -CH (OMe) - _{(CH 2) 2 - 9-9 2,4,6} -Me 3 Me Me Me 9-10 2,4,6-Me 3 Me - (CH 2) 5 - 9-11 2,4,6-Me 3 _{Me - (CH 2) 2 -CHMe-} (CH 2) 2 - 9-12 2,4,6-Me 3 Me - (CH 2) 2 -CH (OMe) - (CH 2) 2 - 9-13 2 _{, 6-Me 2 Me Me Me} 9-14 2,6-Me 2 Me - (CH 2) 5 - 9-15 2,6-Me 2 Me - (CH 2) 2 -CHMe- (CH 2) 2 - 9-16 2,6-Me ₂ Me-(CH ₂ ) ₂ -CH (OMe)-(CH ₂ ) ₂ -────────────────────── ──────────────

[0107]

[Table 10]

[0108]

Embedded image ──────────────────────────────────── Compound number (A) _n R ¹ R ⁴ ──── ──────────────────────────────── 10-1 2,6-Me ₂ CH ₂ OMe CH ₂ OMe 10-2 2,6-Me ₂ CH ₂ OMe CH ₂ OEt 10-3 2,6-Me ₂ CH ₂ OMe CH ₂ OPr 10-4 2,6-Me ₂ CH ₂ OMe CH ₂ OiPr 10-5 2,6-Me ₂ CH ₂ OMe CH ₂ OBu 10-6 2,6-Me ₂ CH ₂ OMe CH ₂ OiBu 10-7 2,6-Me ₂ CH ₂ OMe CH ₂ OsBu 10-8 2,6-Me ₂ CH ₂ OMe CH ₂ OtBu 10-9 2,6-Me ₂ CH ₂ OMe CH ₂ OPh 10-10 2,6-Me ₂ CH ₂ OMe CH ₂ SMe 10-11 2,6-Me ₂ CH ₂ OMe CH ₂ CN 10-12 2,6-Me ₂ CH ₂ OMe CH ₂ C (O) OEt 10-13 2,6-Me ₂ CH ₂ OMe CH ₂ CH = CH ₂ 10-14 2,6-Me ₂ CH ₂ OMe CH ₂ C≡ CH 10-15 2,6-Me ₂ CH ₂ OMe CH ₂ Ph 10-16 2,6-Me ₂ CH ₂ OEt CH ₂ OMe 10-17 2,6-Me ₂ CH ₂ OEt CH ₂ OEt 10-18 2 , 6-Me ₂ CH ₂ OEt CH ₂ OPr 10-19 2,6-Me ₂ CH ₂ OEt CH ₂ OiPr 10-20 2,6-Me ₂ CH ₂ OEt CH ₂ OBu 10-21 2,6-Me ₂ CH ₂ OEt CH ₂ OiBu 10-22 2,6-Me ₂ CH ₂ OEt CH ₂ OsBu 10-23 2,6-Me ₂ CH ₂ OEt CH ₂ OtBu 10-24 2,6-Me ₂ CH ₂ OEt CH ₂ OPh 10-25 2,6-Me ₂ CH ₂ OEt CH ₂ SMe 10-26 2,6-Me ₂ CH ₂ OEt CH ₂ CN 10 -27 2,6-Me ₂ CH ₂ OEt CH ₂ C (O) OEt 10-28 2,6-Me ₂ CH ₂ OEt CH ₂ CH = CH ₂ 10-29 2,6-Me ₂ CH ₂ OEt CH ₂ C≡CH 10-30 2,6-Me ₂ CH ₂ OEt CH ₂ Ph 10-31 2,6-Me ₂ CH ₂ CH ₂ OMe CH ₂ OMe 10-32 2,6-Me ₂ CH ₂ CH ₂ OMe CH ₂ OEt 10-33 2,6-Me ₂ CH ₂ CH ₂ OMe CH ₂ OPr 10-34 2,6-Me ₂ CH ₂ CH ₂ OMe CH ₂ OiPr 10-35 2,6-Me ₂ CH ₂ CH ₂ OMe CH ₂ OBu 10-36 2,6-Me ₂ CH ₂ CH ₂ OMe CH ₂ OiBu 10-37 2,6-Me ₂ CH ₂ CH ₂ OMe CH ₂ OsBu 10-38 2,6-Me ₂ CH ₂ CH ₂ OMe CH ₂ OtBu 10-39 2,6-Me ₂ CH ₂ CH ₂ OMe CH ₂ OPh 10-40 2,6-Me ₂ CH ₂ CH ₂ OMe CH ₂ SMe 10-41 2,6-Me ₂ CH ₂ CH ₂ OMe CH ₂ CN 10-42 2,6-Me ₂ CH ₂ CH ₂ OMe CH ₂ C (O) OEt 10-43 2,6-Me ₂ CH ₂ CH ₂ OMe CH ₂ CH = CH ₂ 10-44 2 , 6-Me ₂ CH ₂ CH ₂ OMe CH ₂ C≡CH 10-45 2,6-Me ₂ CH ₂ CH ₂ OMe CH ₂ Ph 10-46 2-Me, 6-Cl CH ₂ OMe CH ₂ OMe 10- 47 2-Me, 6-Cl CH ₂ OMe CH ₂ OEt 10-48 2-Me, 6-Cl CH ₂ OMe CH ₂ OPr 10-49 2-Me, 6-Cl CH ₂ OMe CH ₂ OiPr 10-50 2 -Me, 6-Cl CH ₂ OMe CH ₂ OBu 10-51 2-Me, 6-Cl CH ₂ OMe CH ₂ OiBu 10-52 2-Me, 6-Cl CH ₂ OMe CH ₂ OsBu 10-53 2-Me, 6-Cl CH ₂ OMe CH ₂ OtBu 10-54 2-Me, 6-Cl CH ₂ OMe CH ₂ OPh 10-55 2-Me, 6-Cl CH ₂ OMe CH ₂ SMe 10-56 2-Me, 6-Cl CH ₂ OMe CH ₂ CN 10 -57 2-Me, 6-Cl CH ₂ OMe CH ₂ C (O) OEt 10-58 2-Me, 6-Cl CH ₂ OMe CH ₂ CH = CH ₂ 10-59 2-Me, 6-Cl CH ₂ OMe CH ₂ C≡CH 10-60 2-Me, 6-Cl CH ₂ OMe CH ₂ Ph 10-61 2-Me, 6-Cl CH ₂ OEt CH ₂ OMe 10-62 2-Me, 6-Cl CH ₂ OEt CH ₂ OEt 10-63 2-Me, 6-Cl CH ₂ OEt CH ₂ OPr 10-64 2-Me, 6-Cl CH ₂ OEt CH ₂ OiPr 10-65 2-Me, 6-Cl CH ₂ OEt CH ₂ OBu 10-66 2-Me, 6-Cl CH ₂ OEt CH ₂ OiBu 10-67 2-Me, 6-Cl CH ₂ OEt CH ₂ OsBu 10-68 2-Me, 6-Cl CH ₂ OEt CH ₂ OtBu 10-69 2-Me, 6-Cl CH ₂ OEt CH ₂ OPh 10-70 2-Me, 6-Cl CH ₂ OEt CH ₂ SMe 10-71 2-Me, 6-Cl CH ₂ OEt CH ₂ CN 10- 72 2-Me, 6-Cl CH ₂ OEt CH ₂ C (O) OEt 10-73 2-Me, 6-Cl CH ₂ OEt CH ₂ CH = CH ₂ 10-74 2-Me, 6-Cl CH ₂ OEt CH ₂ C≡CH 10-75 2-Me, 6-Cl CH ₂ OEt CH ₂ Ph 10-76 2-Me, 6-Cl CH ₂ CH ₂ OMe CH ₂ OMe 10-77 2-Me, 6-Cl CH ₂ CH ₂ OMe CH ₂ OEt 10-78 2-Me, 6-Cl CH ₂ CH ₂ OMe CH ₂ OPr 10-79 2-Me, 6-Cl CH ₂ CH ₂ OMe CH ₂ OiPr 10-80 2-Me, 6-Cl CH ₂ CH ₂ OMe CH ₂ OBu 10-81 2-Me, 6-Cl CH ₂ CH ₂ OMe CH ₂ OiBu 10-82 2-Me, 6-Cl CH ₂ CH ₂ OMe CH ₂ OsBu 10-83 2-Me, 6-Cl CH ₂ CH ₂ OMe CH ₂ OtBu 10-84 2-Me, 6-Cl CH ₂ CH ₂ OMe CH ₂ OPh 10-85 2-Me, 6-Cl CH ₂ CH ₂ OMe CH ₂ SMe 10-86 2-Me, 6-Cl CH ₂ CH ₂ OMe CH ₂ CN 10-87 2-Me , 6-Cl CH ₂ CH ₂ OMe CH ₂ C (O) OEt 10-89 2-Me, 6-Cl CH ₂ CH ₂ OMe CH ₂ CH = CH ₂ 10-89 2-Me, 6-Cl CH ₂ CH ₂ OMe CH ₂ C≡CH 10-90 2-Me, 6-Cl CH ₂ CH ₂ OMe CH ₂ Ph 10-91 2-Me, 6-Br CH ₂ OMe CH ₂ OMe 10-92 2-Me, 6- Br CH ₂ OMe CH ₂ OEt 10-93 2-Me, 6-Br CH ₂ OMe CH ₂ OPr 10-94 2-Me, 6-Br CH ₂ OMe CH ₂ OiPr 10-95 2-Me, 6-Br CH ₂ OMe CH ₂ OBu 10-96 2-Me, 6-Br CH ₂ OMe CH ₂ OiBu 10-97 2-Me, 6-Br CH ₂ OMe CH ₂ OsBu 10-98 2-Me, 6-Br CH ₂ OMe CH ₂ OtBu 10-99 2-Me, 6-Br CH ₂ OMe CH ₂ OPh 10-100 2-Me, 6-Br CH ₂ OMe CH ₂ SMe 10-102 2-Me, 6-Br CH ₂ OMe CH ₂ C (O) OEt 10-103 2-Me, 6-Br CH ₂ OMe CH ₂ CH = CH ₂ 10-104 2-Me, 6-Br CH ₂ OMe CH ₂ C≡CH 10-105 2-Me, 6 -Br CH ₂ OMe CH ₂ Ph 10-106 2-Me , 6-Br CH ₂ OEt CH ₂ OMe 10-107 2-Me, 6-Br CH ₂ OEt CH ₂ OEt 10-108 2-Me, 6-Br CH ₂ OEt CH ₂ OPr 10-109 2-Me, 6 -Br CH ₂ OEt CH ₂ OiPr 10-110 2-Me, 6-Br CH ₂ OEt CH ₂ OBu 10-111 2-Me, 6-Br CH ₂ OEt CH ₂ OiBu 10-112 2-Me, 6-Br CH ₂ OEt CH ₂ OsBu 10-113 2-Me, 6-Br CH ₂ OEt CH ₂ OtBu 10-114 2-Me, 6-Br CH ₂ OEt CH ₂ OPh 10-115 2-Me, 6-Br CH ₂ OEt CH ₂ SMe 10-116 2-Me, 6-Br CH ₂ OEt CH ₂ CN 10-117 2-Me, 6-Br CH ₂ OEt CH ₂ C (O) OEt 10-118 2-Me, 6-Br CH ₂ OEt CH ₂ CH = CH ₂ 10-119 2-Me, 6-Br CH ₂ OEt CH ₂ C≡CH 10-120 2-Me, 6-Br CH ₂ OEt CH ₂ Ph 10-121 2-Me, 6-Br CH ₂ CH ₂ OMe CH ₂ OMe 10-122 2-Me, 6-Br CH ₂ CH ₂ OMe CH ₂ OEt 10-123 2-Me, 6-Br CH ₂ CH ₂ OMe CH ₂ OPr 10-124 2-Me, 6-Br CH ₂ CH ₂ OMe CH ₂ OiPr 10-125 2-Me, 6-Br CH ₂ CH ₂ OMe CH ₂ OBu 10-126 2-Me, 6-Br CH ₂ CH ₂ OMe CH ₂ OiBu 10-127 2-Me, 6-Br CH ₂ CH ₂ OMe CH ₂ OsBu 10-128 2-Me, 6-Br CH ₂ CH ₂ OMe CH ₂ OtBu 10-129 2-Me, 6-Br CH ₂ CH ₂ OMe CH ₂ OPh 10-130 2-Me, 6-Br CH ₂ CH ₂ OMe CH ₂ SMe 10-131 2-Me, 6-Br CH ₂ CH ₂ OMe CH ₂ CN 10-132 2-Me, 6- Br CH ₂ CH ₂ OMe CH ₂ C (O) OEt 10-133 2-Me, 6-Br CH ₂ CH ₂ OMe CH ₂ CH = CH ₂ 10-134 2-Me, 6-Br CH ₂ CH ₂ OMe CH ₂ C≡CH 10- 135 2-Me, 6-Br CH ₂ CH ₂ OMe CH ₂ Ph 10-136 2-Cl, 6-F CH ₂ OMe CH ₂ OMe 10-137 2-Br, 4,6-Me ₂ CH ₂ OMe CH ₂ OMe 10-138 2,3,6-Me ₃ CH ₂ CH ₂ OMe COcPr 10-139 2,4-Cl ₂ , 6-Me CH ₂ OMe COcPr 10-140 2,4,6-Me ₃ , 3-Cl CH ₂ OMe COcPr 10-141 2,3,4,6-Me ₄ CH ₂ OMe COcPr 10-142 2,6-Me ₂ , 4-tBu CH ₂ OMe COcPr 10-143 2,6-Me ₂ , 4- OMe CH ₂ OMe CO (2-OMe-Ph) 10-144 2,6-Me ₂ , 4-OMe CH ₂ OMe COcPr 10-145 2,6-Me ₂ , 4-OMe CH ₂ OEt CO (2-OMe -Ph) 10-146 2,6-Me ₂ CH ₂ OMe Ac 10-147 2,6-Me ₂ CH ₂ OMe COiPr 10-148 2,6-Me ₂ CH ₂ OMe COcPr 10-149 2,6-Me ₂ CH ₂ OMe COcPr (1-Me) 10-150 2,6-Me ₂ CH ₂ OMe COcPr (2-Me) 10-151 2,6-Me ₂ CH ₂ OMe COcPr (1-Me, 2,2- Cl ₂ ) 10-152 2,6-Me ₂ CH ₂ OMe COC (Me) ₂ Et 10-153 2,6-Me ₂ CH ₂ OMe COC (Me) ₂ CH ₂ Cl 10-154 2,6-Me ₂ CH ₂ OMe COCH ₂ CH ₂ Cl 10-155 2,6-Me ₂ CH ₂ OMe COcBu 10-156 2,6-Me ₂ CH ₂ OMe COcPent 10-157 2,6-Me ₂ CH ₂ OMe COcHex 10-158 2,6-Me ₂ CH ₂ OMe COCCl = CH ₂ 10-159 2 , 6-Me ₂ CH ₂ OMe CO (2-Cl-Ph) 10-160 2,6-Me ₂ CH ₂ OMe CO (2-Me-Ph) 10-161 2,6-Me ₂ CH ₂ OMe CO ₂ Me 10-162 2,6-Me ₂ CH ₂ OMe CO ₂ Et 10-163 2,6-Me ₂ CH ₂ OMe CO (S) Me 10-164 2,6-Me ₂ CH ₂ OMe CONMe ₂ 10-165 2,6-Me ₂ CH ₂ OMe C (S) NMe ₂ 10-166 2,6-Me ₂ CH ₂ OMe CH ₂ OEt 10-167 2,6-Me ₂ CH ₂ OEt COcPr 10-168 2,6- Me ₂ CH ₂ OEt COcPr (1-Me) 10-169 2,6-Me ₂ CH ₂ OEt COcPr (1-Ph) 10-170 2,6-Me ₂ CH ₂ OEt COcPr (1- (4-OEt- Ph), 2,2-Cl ₂ ) 10-171 2,6-Me ₂ CH ₂ OEt COcBu 10-172 2,6-Me ₂ CH ₂ OEt COCCl = CH ₂ 10-173 2,6-Me ₂ CH ₂ OEt CO (3-Q ³ ) 10-174 2,6-Me ₂ CH ₂ OEt CO (2-Cl-Ph) 10-175 2,6-Me ₂ CH ₂ OEt CO (2-Me-Ph) 10- 176 2,6-Me ₂ CH ₂ OEt CO (2-OMe-Ph) 10-177 2,6-Me ₂ CH ₂ OEt P (S) (OEt) ₂ 10-178 2,6-Me ₂ CH ₂ CH ₂ OMe COcPr 10-179 2,6-Me ₂ CH ₂ CH ₂ OMe COcPr (1-Me) 10-180 2,6-Me ₂ CH ₂ CH ₂ OMe COcBu 10-181 2,6-Me ₂ CH ₂ CH ₂ OMe COC (Me) ₂ Et 10-182 2,6-Me ₂ CH ₂ CH ₂ OMe COC (Me) ₂ CH ₂ Cl 10-183 2,6-Me ₂ CH ₂ CH ₂ OMe COC (Me) ₂ OAc 10-184 2,6-Me ₂ CH ₂ CH ₂ OMe CO (2-Me-Ph) 10-185 2,6-Me ₂ CH ₂ CH ₂ OMe CO (2-Cl-Ph) 10-186 2,6-Me ₂ CH ₂ CH ₂ OMe CO (2-OMe-Ph) 10-187 2,6-Me ₂ CH ₂ CH ₂ OMe CO ₂ Me 10-188 2,6-Me ₂ CH ₂ CH ₂ OMe CH ₂ CN 10-189 2,6-Me ₂ CH ₂ CH ₂ OMe CH ₂ OMe 10-190 2,6-Me ₂ CH ₂ CH ₂ OMe CH ₂ SMe 10- 191 2,6-Me ₂ H COcPr 10-192 2,6-Me ₂ Pr COcPr 10-193 2,6-Me ₂ cPr COcPr 10-194 2,6-Me ₂ CH ₂ C≡CH COcPr 10-195 2 , 6-Me ₂ CH ₂ CN COCH ₂ tBu 10-196 2,6-Me ₂ CH ₂ CH ₂ CH ₂ OMe COcPr 10-197 2,6-Me ₂ CH (Me) CH ₂ OMe COcPr 10-198 2, 6-Me ₂ CH ₂ (3-Thf) CO (2-OMe-Ph) 10-199 2,6-Me ₂ CH ₂ (3-Thf) CO (2-Me-Ph) 10-200 2,6- Me ₂ 3-Thf COcPr 10-201 2,6-Me ₂ 3-Thf CO (2-OMe-Ph) 10-202 2,6-Me ₂ CH ₂ OMe CO (3-Me-3-Q ³ ) 10 -203 2,6-Me ₂ CH ₂ OMe COC (Me) ₂ OMe 10-204 2,6-Me ₂ CH ₂ OMe COC (Me) ₂ OEt 10-205 2,6-Me ₂ CH ₂ OMe COC (Me ) (Et) OMe 10-206 2,6-Me ₂ CH ₂ OMe COC (Et) ₂ OMe 10-207 2,6-Me ₂ CH ₂ OMe COcPent (1-OMe) 10-208 2,6-Me ₂ CH ₂ OMe COcHex (1-OMe) 10-209 2,6-Me ₂ CH ₂ OEt COC (Me) ₂ OMe 10-210 2,6-Me ₂ CH ₂ OEt COC (Me) ₂ OEt 10-211 2, 6-Me ₂ CH ₂ OEt COC (Me) (Et) OMe 10-212 2,6-Me ₂ CH ₂ OEt COC (Et) ₂ OMe 10-213 2,6-Me ₂ CH ₂ OEt COcPent (1-OMe) 10-214 2,6-Me ₂ CH ₂ OEt COcHex (1-OMe) 10-215 2,6-Me ₂ CH ₂ CH ₂ OMe COC (Me) ₂ OMe 10-216 2,6-Me ₂ CH ₂ CH ₂ OMe COC (Me) ₂ OEt 10-217 2,6-Me ₂ CH ₂ CH ₂ OMe COC (Me) ( Et) OMe 10-218 2,6-Me ₂ CH ₂ CH ₂ OMe COC (Et) ₂ OMe 10-219 2,6-Me ₂ CH ₂ CH ₂ OMe COcPent (1-OMe) 10-220 2,6- Me ₂ CH ₂ CH ₂ OMe COcHex (1-OMe) 10-221 2,4-Cl ₂ CH ₂ OMe COcPr 10-222 2,4-Cl ₂ CH ₂ OMe COcPr (1-Me) 10-223 2,4 -Cl ₂ CH ₂ OMe COcPr (2-Me) 10-224 2,4-Cl ₂ CH ₂ OMe COcPr (1-CN) 10-225 2,4-Cl ₂ CH ₂ OMe COcPr (1-Me, 2, 2-Cl ₂ ) 10-226 2,4-Cl ₂ CH ₂ OMe COcPr (2,2,3,3-Me ₄ ) 10-227 2,4-Cl ₂ CH ₂ OMe COcBu 10-228 2,4- Cl ₂ CH ₂ OMe CO (3-Me-3-Q ³ ) 10-229 2,4-Cl ₂ CH ₂ OMe COCClC = CH ₂ 10-230 2,4-Cl ₂ CH ₂ OMe CO (2-Cl- Ph) 10-231 2,4-Cl ₂ CH ₂ OEt COcPr 10-232 2,4-Cl ₂ CH ₂ OEt COcPr (1-Me) 10-233 2,4-Cl ₂ CH ₂ OEt COcPr (1-CN ) 10-234 2,4-Cl ₂ CH ₂ OEt COcBu 10-235 2,4-Cl ₂ CH ₂ OEt CO (3-Me-3-Q ³ ) 10-236 2,4-Cl ₂ CH ₂ OEt COCClC = CH ₂ 10-237 2,4-Cl ₂ CH ₂ OEt COPh 10-238 2,4-Cl ₂ CH ₂ OEt CO (2-Me-Ph) 10-239 2,4-Cl ₂ CH ₂ OEt CO (2-Cl-Ph) 10-240 2,4-Cl ₂ CH ₂ OEt CO (2-OMe-Ph) 10-241 2,4-Cl ₂ CH ₂ OEt CO (3-OMe-Ph) 10-242 2,4-Cl ₂ CH ₂ OEt CO (4-OMe-Ph) 10-243 2,4-Cl ₂ CH ₂ OEt CO (2-F-Ph) 10-244 2,4-Cl ₂ CH ₂ OEt CO (2,4- (OMe) ₂ -Ph) 10-245 2,4-Cl ₂ CH ₂ OEt CO (2 , 6- (OMe) ₂ -Ph) 10-246 2,4-Cl ₂ CH ₂ OEt CO (3,5- (OMe) ₂ -Ph) 10-247 2,4-Cl ₂ CH ₂ OEt CO (2 , 4-F ₂ -Ph) 10-248 2,4-Cl ₂ CH ₂ OEt CO (3-Pyr) 10-249 2,4-Cl ₂ CH ₂ OEt CO (2-OMe-3-Pyr) 10- 250 2,4-Cl ₂ CH ₂ CH ₂ OMe COcPr 10-251 2,4-Cl ₂ CH ₂ CH ₂ OMe COcBu 10-252 2,4-Cl ₂ CH ₂ CH ₂ OMe COPh 10-253 2,4- Cl ₂ CH ₂ CH ₂ OMe CO (2-Me-Ph) 10-254 2,4-Cl ₂ CH ₂ CH ₂ OMe CO (2-OMe-Ph) 10-255 2,4-Cl ₂ CH ₂ CH ₂ OMe CO (3-Pyr) 10-256 2-Cl CH ₂ OMe COcPr 10-257 2-Cl CH ₂ OMe COcPr (1-Me) 10-258 2-Cl CH ₂ OMe CO (2-OMe-Ph) 10 -259 2-Cl CH ₂ OEt COcPr 10-260 2-Cl CH ₂ OEt COcPr (1-Me) 10-261 2-Cl CH ₂ OEt COcPr (1-CN) 10-262 2-Cl CH ₂ OEt COcBu 10 -263 2-Cl CH ₂ OEt COcPent 10-264 2-Cl CH ₂ OEt CO (3-Me-3-Q ³ ) 10-265 2-Cl CH ₂ OEt CO (2-Me-Ph ) 10-266 2-Cl CH ₂ OEt CO (2-OMe-Ph) 10-267 2-Cl CH ₂ OEt P (S) (OEt) ₂ 10-268 2-Cl CH ₂ CH ₂ OMe COcPr 10-269 2-Cl CH ₂ CH ₂ OMe COcPr (1-Me) 10-270 2-Cl CH ₂ CH ₂ OMe COcPr (1-CN) 10-271 2-Cl CH ₂ CH ₂ OMe COcBu 10-272 2-Cl CH ₂ CH ₂ OMe COcPent 10-273 2-Cl CH ₂ CH ₂ OMe CO (3-Me-3-Q ³ ) 10-274 2-Cl CH ₂ CH ₂ OMe CO (2-Me-Ph) ──── ────────────────────────────────

[0109]

[Table 11]

[0110]

Embedded image ──────────────────────────────────── Compound number (A) _n R ¹ R ² R ³ R ⁴ ──────────────────────────────────── 11-1 2,6-Me ₂ CH ₂ OMe Me CH ₂ CH ₂ (2-Q ⁴ ) H 11-2 2,6-Me ₂ CH ₂ OMe Me CH ₂ (2-Thf) H 11-3 2,6-Me ₂ CH ₂ OMe Me CH ₂ CH = CH ₂ H 11-4 2,6-Me ₂ CH ₂ OMe Me CH ₂ Ph H 11-5 2,6-Me ₂ CH ₂ OMe Me CH ₂ cHex H 11-6 2,6-Me ₂ CH ₂ OMe Me CH ₂ CH ₂ Ph H 11-7 2,6-Me ₂ CH ₂ OMe Me CH ₂ CH ₂ OMe H 11-8 2,6-Me ₂ CH ₂ OMe-(CH ₂ ) ₂ -O- (CH ₂ ) _2- H 11-9 2,6-Me ₂ CH ₂ OMe-(CH ₂ ) ₂ -O- (CH ₂ ) ₂ -CO (2-OMe-Ph) 11-10 2,6-Me ₂ CH ₂ OEt Me CH ₂ (4-Cl-Ph) H 11-11 2,6-Me ₂ CH ₂ OEt Me CH ₂ (2-Cl-Ph) H 11-12 2,6-Me ₂ CH ₂ OEt-(CH ₂ ) ₃ -COcPr 11-13 2,4-Cl ₂ CH ₂ OMe Me Et H 11-14 2,4-Cl ₂ CH ₂ OMe Me CH ₂ (4-OMe-Ph) H 11-15 2,4-Cl ₂ CH ₂ OMe Me CH ₂ (3-Me-Ph) H 11-16 2,4-Cl ₂ CH ₂ OMe Me CH ₂ (3-OMe-Ph) H 11-17 2,4-Cl ₂ CH ₂ OEt Me Et H 11-18 2,4-Cl ₂ C H ₂ OEt Me Et CO (2-OMe-Ph) 11-19 2,4-Cl ₂ CH ₂ OEt Me iPr H 11-20 2,4-Cl ₂ CH ₂ OEt-(CH ₂ ) ₃ -H 11- 21 2,4-Cl ₂ CH ₂ OEt-(CH ₂ ) ₃ -CH ₂ OEt 11-22 2,4-Cl ₂ CH ₂ OEt Me CH ₂ (2-Cl-Ph) H 11-23 2,4- Cl ₂ CH ₂ OEt Me CH ₂ (3-Cl-Ph) H 11-24 2,4-Cl ₂ CH ₂ OEt Me CH ₂ (4-Cl-Ph) H 11-25 2,4-Cl ₂ CH ₂ OEt Me CH ₂ (4-Cl-Ph) CO (2-OMe-Ph) 11-26 2,4-Cl ₂ CH ₂ OEt Me CH ₂ (2-Me-Ph) H 11-27 2,4-Cl ₂ CH ₂ OEt Me CH ₂ (3-Me-Ph) H 11-28 2,4-Cl ₂ CH ₂ OEt Me CH ₂ (4-OMe-Ph) H 11-29 2,4-Cl ₂ CH ₂ OEt Me 4-OMe-Ph CO ₂ Me 11-30 2,6-Me ₂ Me-(CH ₂ ) ₂ -CH (OCH ₂ OMe)-(CH ₂ ) ₂ -H 11-31 2,6-Me ₂ Me -(CH ₂ ) ₂ -CH (OCH ₂ OMe)-(CH ₂ ) ₂ -COcPr 11-32 2,6-Me ₂ Me-(CH ₂ ) ₂ -CH (OCH ₂ OEt)-(CH ₂ ) ₂ -H 11-33 2,6-Me ₂ Me-(CH ₂ ) ₂ -CH (OCH ₂ OEt)-(CH ₂ ) ₂ -COMe 11-34 2,6-Me ₂ Me-(CH ₂ ) _2- CH (OCH ₂ OEt)-(CH ₂ ) ₂ -COEt 11-35 2,6-Me ₂ Me-(CH ₂ ) ₂ -CH (OCH ₂ OEt)-(CH ₂ ) ₂ -COiPr 11-36 2, 6-Me ₂ Me-(CH ₂ ) ₂ -CH (OCH ₂ OEt)-(CH ₂ ) ₂ -COcPr 11-37 2,6-Me ₂ Me-(CH ₂ ) ₂ -C (= N-OMe) -(CH ₂ ) ₂ -H 11-38 2,6-Me ₂ Me-(CH ₂ ) ₂ -C (= N-OMe)-(CH ₂ ) ₂ -COMe 11-39 2,6-Me ₂ Me-(CH ₂ ) ₂ -C (= N-OMe)-( CH ₂ ) ₂ -COEt 11-40 2,6-Me ₂ Me-(CH ₂ ) ₂ -C (= N-OMe)-(CH ₂ ) ₂ -COiPr 11-41 2,6-Me ₂ Me-( CH ₂ ) ₂ -C (= N-OMe)-(CH ₂ ) ₂ -COcPr 11-42 2,6-Me ₂ Me-(CH ₂ ) ₂ -C (-O (CH ₂ ) ₂ O-)- (CH ₂ ) ₂ -H 11-43 2,6-Me ₂ Me-(CH ₂ ) ₂ -C (-O (CH ₂ ) ₂ O-)-(CH ₂ ) ₂ -COMe 11-44 2,6 -Me ₂ Me-(CH ₂ ) ₂ -C (-O (CH ₂ ) ₂ O-)-(CH ₂ ) ₂ -COEt 11-45 2,6-Me ₂ Me-(CH ₂ ) ₂ -C ( -O (CH ₂ ) ₂ O-)-(CH ₂ ) ₂ -COiPr 11-46 2,6-Me ₂ Me-(CH ₂ ) ₂ -C (-O (CH ₂ ) ₂ O-)-(CH ₂ ) ₂ -COcPr 11-47 2,6-Me ₂ Me-(CH ₂ ) ₂ -C (-O (CH ₂ ) ₃ O-)-(CH ₂ ) ₂ -H 11-48 2,6-Me ₂ Me-(CH ₂ ) ₂ -C (-O (CH ₂ ) ₃ O-)-(CH ₂ ) ₂ -COMe 11-49 2,6-Me ₂ Me-(CH ₂ ) ₂ -C (-O (CH ₂ ) ₃ O-)-(CH ₂ ) ₂ -COEt 11-50 2,6-Me ₂ Me-(CH ₂ ) ₂ -C (-O (CH ₂ ) ₃ O-)-(CH ₂ ) ₂ -COiPr 11-51 2,6-Me ₂ Me-(CH ₂ ) ₂ -C (-O (CH ₂ ) ₃ O-)-(CH ₂ ) ₂ -COcPr 11-52 2,6-Me ₂ CH ₂ OMe-(CH ₂ ) ₂ -CH (OCH ₂ OMe)-(CH ₂ ) ₂ -H 11-53 2,6-Me ₂ CH ₂ OMe-(CH ₂ ) ₂ -CH (OCH ₂ OMe)-( CH ₂ ) ₂ -COcPr 11- 54 2,6-Me ₂ CH ₂ OMe-(CH ₂ ) ₂ -CH (OCH ₂ OEt)-(CH ₂ ) ₂ -H 11-55 2,6-Me ₂ CH ₂ OMe-(CH ₂ ) _2- CH (OCH ₂ OEt)-(CH ₂ ) ₂ -COcPr 11-56 2,6-Me ₂ CH ₂ OMe-(CH ₂ ) ₂ -C (-O (CH ₂ ) ₂ O-)-(CH ₂ ) ₂ -H 11-57 2,6-Me ₂ CH ₂ OMe-(CH ₂ ) ₂ -C (-O (CH ₂ ) ₂ O-)-(CH ₂ ) ₂ -COcPr 11-58 2,6-Me ₂ CH ₂ OMe-(CH ₂ ) ₂ -C (-O (CH ₂ ) ₂ O-)-(CH ₂ ) ₂ -COiPr 11-59 2,6-Me ₂ CH ₂ OMe-(CH ₂ ) _2- C (-O (CH ₂ ) ₂ O-)-(CH ₂ ) ₂ -COtBu 11-60 2,6-Me ₂ CH ₂ OMe-(CH ₂ ) ₂ -C (-O (CH ₂ ) ₂ O- )-(CH ₂ ) ₂ -CO ₂ Et 11-61 2,6-Me ₂ CH ₂ OMe-(CH ₂ ) ₂ -C (-O (CH ₂ ) ₃ O-)-(CH ₂ ) ₂ -COcPr 11-62 2,6-Me ₂ CH ₂ OEt-(CH ₂ ) ₂ -CH (OCH ₂ OMe)-(CH ₂ ) ₂ -COcPr 11-63 2,6-Me ₂ CH ₂ OEt-(CH ₂ ) ₂ -CH (OCH ₂ OEt)-(CH ₂ ) ₂ -COcPr 11-64 2,6-Me ₂ CH ₂ OEt-(CH ₂ ) ₂ -C (= N-OMe)-(CH ₂ ) ₂ -COcPr 11-65 2,6-Me ₂ CH ₂ OEt-(CH ₂ ) ₂ -C (-O (CH ₂ ) ₂ O-)-(CH ₂ ) ₂ -H 11-66 2,6-Me ₂ CH ₂ OEt-(CH ₂ ) ₂ -C (-O (CH ₂ ) ₂ O-)-(CH ₂ ) ₂ -COEt 11-67 2,6-Me ₂ CH ₂ OEt-(CH ₂ ) ₂ -C (- O (CH ₂ ) ₂ O-)-(CH ₂ ) ₂ -COiPr 11-68 2,6-Me ₂ CH ₂ OEt-(CH ₂ ) ₂ -C (-O (CH ₂ ) ₂ O-)-(CH ₂ ) ₂ -COcPr 11-69 2,6-Me ₂ CH ₂ OEt-(CH ₂ ) ₂ -C (-O (CH ₂ ) ₂ O-)-(CH ₂ ) ₂ -COtBu 11-70 2,6-Me ₂ CH ₂ OEt-(CH ₂ ) ₂ -C (-O (CH ₂ ) ₂ O-)-(CH ₂ ) _2- CO ₂ Et 11-71 2,6-Me ₂ CH ₂ CH ₂ OMe-(CH ₂ ) ₂ -C (-O (CH ₂ ) ₂ O-)-(CH ₂ ) ₂ -H 11-72 2,6 -Me ₂ CH ₂ CH ₂ OMe-(CH ₂ ) ₂ -C (-O (CH ₂ ) ₂ O-)-(CH ₂ ) ₂ -COEt 11-73 2,6-Me ₂ CH ₂ CH ₂ OMe- (CH ₂ ) ₂ -C (-O (CH ₂ ) ₂ O-)-(CH ₂ ) ₂ -COiPr 11-74 2,6-Me ₂ CH ₂ CH ₂ OMe-(CH ₂ ) ₂ -C (- O (CH ₂ ) ₂ O-)-(CH ₂ ) ₂ -COcPr 11-75 2,6-Me ₂ CH ₂ CH ₂ OMe-(CH ₂ ) ₂ -C (-O (CH ₂ ) ₂ O-) -(CH ₂ ) ₂ -COtBu 11-76 2,6-Me ₂ CH ₂ CH ₂ OMe-(CH ₂ ) ₂ -C (-O (CH ₂ ) ₂ O-)-(CH ₂ ) ₂ -CO ₂ Et 11-77 2,6-Me ₂ Me-(CH ₂ ) ₂ -C (-O (CH ₂ ) ₂ O-)-(CH ₂ ) ₂ -CO (2-OMe-Ph) 11-78 2, 6-Me ₂ CH ₂ OEt-(CH ₂ ) ₂ -CH (OCH ₂ Et)-(CH ₂ ) ₂ -H 11-79 2,6-Me ₂ H-(CH ₂ ) ₂ -C (-O ( CH ₂ ) ₂ O-)-(CH ₂ ) ₂ -COcPr 11-80 2,6-Me ₂ CH ₂ OEt-(CH ₂ ) ₂ -C (-O (CH ₂ ) ₂ O-)-(CH ₂ ) ₂ -COMe 11-81 2,6-Me ₂ CH ₂ CH ₂ OMe-(CH ₂ ) ₂ -C (-O (CH ₂ ) ₂ O-)-(CH ₂ ) ₂ -COMe 11-82 2,6-Me ₂ CH ₂ CH ₂ OMe-(CH ₂ ) ₂ -CH (OCH ₂ Et)-(CH ₂ ) ₂ -H 11-83 2,6-Me ₂ CH ₂ CH ₂ OMe-(CH ₂ ) ₂ -CH (OCH ₂ Et)-(CH ₂ ) ₂ -COMe 11-84 2,6-Me ₂ CH ₂ CH ₂ OMe-(CH ₂ ) ₂ -CH (OCH ₂ Et)-(CH ₂ ) ₂ -COEt 11-85 2,6-Me ₂ CH ₂ CH ₂ OMe-(CH ₂ ) ₂ -CH (OCH ₂ Et)-(CH ₂ ) ₂ -COiPr 11-86 2,6-Me ₂ CH ₂ CH ₂ OMe-(CH ₂ ) ₂ -CH (OCH ₂ Et)-(CH ₂ ) ₂ -COcPr 11-87 2,6-Me ₂ CH ₂ CH ₂ OMe-(CH ₂ ) ₂ -CH (OCH ₂ Et)- (CH ₂ ) ₂ -CO ₂ Et 11-88 2,6-Me ₂ CH ₂ CH ₂ OMe-(CH ₂ ) ₂ -C (-O (CH ₂ ) ₃ O-)-(CH ₂ ) ₂ -H 11-89 2,6-Me ₂ CH ₂ CH ₂ OMe-(CH ₂ ) ₂ -C (-O (CH ₂ ) ₃ O-)-(CH ₂ ) ₂ -COMe 11-90 2,6-Me ₂ CH ₂ CH ₂ OMe-(CH ₂ ) ₂ -C (-O (CH ₂ ) ₃ O-)-(CH ₂ ) ₂ -COEt 11-91 2,6-Me ₂ CH ₂ CH ₂ OMe-(CH ₂ ) ₂ -C (-O (CH ₂ ) ₃ O-)-(CH ₂ ) ₂ -COiPr 11-92 2,6-Me ₂ CH ₂ CH ₂ OMe-(CH ₂ ) ₂ -C (-O (CH ₂ ) ₃ O-)-(CH ₂ ) ₂ -COcPr 11-93 2,6-Me ₂ CH ₂ CH ₂ OMe-(CH ₂ ) ₂ -C (-O (CH ₂ ) ₃ O-)-(CH ₂ ) ₂ -CO ₂ Et 11-94 2,6-Me ₂ CH ₂ OEt-(CH ₂ ) ₂ -CH (OCH ₂ Et)-(CH ₂ ) ₂ -COMe 11-95 2,6-Me ₂ CH ₂ OEt-(CH ₂ ) ₂ -CH (OCH ₂ Et)-(CH ₂ ) ₂ -COEt 11-96 2,6-Me ₂ CH ₂ OEt-(CH ₂ ) ₂ -CH (OCH ₂ Et)-(CH ₂ ) ₂ -COiPr 11-97 2,6-Me ₂ CH ₂ OEt -(CH ₂ ) ₂ -CH (OCH ₂ Et)-(CH ₂ ) ₂ -CO ₂ Et 11-98 2,6-Me ₂ CH ₂ OEt-(CH ₂ ) ₂ -C (-O (CH ₂ ) ₃ O-)-(CH ₂ ) ₂ -H 11-99 2,6-Me ₂ CH ₂ OEt-(CH ₂ ) ₂ -C (-O (CH ₂ ) ₃ O-)-(CH ₂ ) _2- COMe 11-100 2,6-Me ₂ CH ₂ OEt-(CH ₂ ) ₂ -C (-O (CH ₂ ) ₃ O-)-(CH ₂ ) ₂ -COEt 11-101 2,6-Me ₂ CH ₂ OEt-(CH ₂ ) ₂ -C (-O (CH ₂ ) ₃ O-)-(CH ₂ ) ₂ -COiPr 11-102 2,6-Me ₂ CH ₂ OEt-(CH ₂ ) ₂ -C ( -O (CH ₂ ) ₃ O-)-(CH ₂ ) ₂ -COcPr 11-103 2,6-Me ₂ CH ₂ OEt-(CH ₂ ) ₂ -C (-O (CH ₂ ) ₃ O-)- (CH ₂ ) ₂ -CO ₂ Et ────────────────────────────────────

[0111]

[Table 12]

[0112]

Embedded image ──────────────────────────────────── Compound number (A) _n R ¹ R ² R ³ R ⁴ ──────────────────────────────────── 12-1 2,6-Me ₂ Me-(CH ₂ ) ₅ -H 12-2 2,6-Me ₂ Me-(CH ₂ ) ₅ -COMe 12-3 2,6-Me ₂ Me-(CH ₂ ) ₅ -COEt 12-4 2,6-Me ₂ Me -(CH ₂ ) ₅ -COiPr 12-5 2,6-Me ₂ Me-(CH ₂ ) ₅ -COcPr 12-6 2,6-Me ₂ Me-(CH ₂ ) ₅ -CO ₂ Me 12-7 2 , 6-Me ₂ Me-(CH ₂ ) ₅ -CO ₂ Et 12-8 2,6-Me ₂ Me-(CH ₂ ) ₅ -CH ₂ OEt 12-9 2,6-Me ₂ Et-(CH ₂ ) ₅ -H 12-10 2,6-Me ₂ Et-(CH ₂ ) ₅ -COMe 12-11 2,6-Me ₂ Et-(CH ₂ ) ₅ -COEt 12-12 2,6-Me ₂ Et -(CH ₂ ) ₅ -COiPr 12-13 2,6-Me ₂ Et-(CH ₂ ) ₅ -COcPr 12-14 2,6-Me ₂ Et-(CH ₂ ) ₅ -CO ₂ Me 12-15 2 , 6-Me ₂ Et-(CH ₂ ) ₅ -CO ₂ Et 12-16 2,6-Me ₂ Et-(CH ₂ ) ₅ -CH ₂ OEt 12-17 2,6-Me ₂ Me-(CH ₂ ) ₂ -CH (Me)-(CH ₂ ) ₂ -H 12-18 2,6-Me ₂ Me-(CH ₂ ) ₂ -CH (Me)-(CH ₂ ) ₂ -COMe 12-19 2,6 -Me ₂ Me-(CH ₂ ) ₂ -CH (Me)-(CH ₂ ) ₂ -COEt 12-20 2,6-Me ₂ Me-(CH ₂ ) ₂ -CH (Me)-(CH ₂ ) ₂ -COiPr 12-21 2,6-Me ₂ Me-(CH ₂ ) ₂ -CH (Me) -(CH ₂ ) ₂ -COcPr 12-22 2,6-Me ₂ Me-(CH ₂ ) ₂ -CH (Me)-(CH ₂ ) ₂ -CO ₂ Me 12-23 2,6-Me ₂ Me- (CH ₂ ) ₂ -CH (Me)-(CH ₂ ) ₂ -CO ₂ Et 12-24 2,6-Me ₂ Me-(CH ₂ ) ₂ -CH (Me)-(CH ₂ ) ₂ -CH ₂ OEt 12-25 2,6-Me ₂ Et-(CH ₂ ) ₂ -CH (Me)-(CH ₂ ) ₂ -H 12-26 2,6-Me ₂ Et-(CH ₂ ) ₂ -CH (Me )-(CH ₂ ) ₂ -COMe 12-27 2,6-Me ₂ Et-(CH ₂ ) ₂ -CH (Me)-(CH ₂ ) ₂ -COEt 12-28 2,6-Me ₂ Et-( CH ₂ ) ₂ -CH (Me)-(CH ₂ ) ₂ -COiPr 12-29 2,6-Me ₂ Et-(CH ₂ ) ₂ -CH (Me)-(CH ₂ ) ₂ -COcPr 12-30 2 , 6-Me ₂ Et-(CH ₂ ) ₂ -CH (Me)-(CH ₂ ) ₂ -CO ₂ Me 12-31 2,6-Me ₂ Et-(CH ₂ ) ₂ -CH (Me)-( CH ₂ ) ₂ -CO ₂ Et 12-32 2,6-Me ₂ Et-(CH ₂ ) ₂ -CH (Me)-(CH ₂ ) ₂ -CH ₂ OEt 12-33 2,6-Me ₂ Me- (CH ₂ ) ₂ -CH (OMe)-(CH ₂ ) ₂ -H 12-34 2,6-Me ₂ Me-(CH ₂ ) ₂ -CH (OMe)-(CH ₂ ) ₂ -COMe 12-35 2,6-Me ₂ Me-(CH ₂ ) ₂ -CH (OMe)-(CH ₂ ) ₂ -COEt 12-36 2,6-Me ₂ Me-(CH ₂ ) ₂ -CH (OMe)-(CH ₂ ) ₂ -COiPr 12-37 2,6-Me ₂ Me-(CH ₂ ) ₂ -CH (OMe)-(CH ₂ ) ₂ -COcPr 12- 38 2,6-Me ₂ Me-(CH ₂ ) ₂ -CH (OMe)-(CH ₂ ) ₂ -CO ₂ Me 12-39 2,6-Me ₂ Me-(CH ₂ ) ₂ -CH (OMe) -(CH ₂ ) ₂ -CO ₂ Et 12-40 2,6-Me ₂ Me-(CH ₂ ) ₂ -CH (OMe)-(CH ₂ ) ₂ -CH ₂ OEt 12-41 2,6-Me _{2 Et - (CH 2) 2 -CH} (OMe) - (CH 2) 2 - H 12-42 2,6-Me 2 Et - (CH 2) 2 -CH (OMe) - (CH 2) 2 - COMe 12 -43 2,6-Me ₂ Et-(CH ₂ ) ₂ -CH (OMe)-(CH ₂ ) ₂ -COEt 12-44 2,6-Me ₂ Et-(CH ₂ ) ₂ -CH (OMe)- (CH ₂ ) ₂ -COiPr 12-45 2,6-Me ₂ Et-(CH ₂ ) ₂ -CH (OMe)-(CH ₂ ) ₂ -COcPr 12-46 2,6-Me ₂ Et-(CH ₂ ) ₂ -CH (OMe)-(CH ₂ ) ₂ -CO ₂ Me 12-47 2,6-Me ₂ Et-(CH ₂ ) ₂ -CH (OMe)-(CH ₂ ) ₂ -CO ₂ Et 12- 48 2,6-Me ₂ Et-(CH ₂ ) ₂ -CH (OMe)-(CH ₂ ) ₂ -CH ₂ OEt 12-49 2,6-Me ₂ Me-(CH ₂ ) ₂ -CH (NMe ₂ )-(CH ₂ ) ₂ -H 12-50 2,6-Me ₂ Me-(CH ₂ ) ₂ -CH (NMe ₂ )-(CH ₂ ) ₂ -COMe 12-51 2,6-Me ₂ Me- (CH ₂ ) ₂ -CH (NMe ₂ )-(CH ₂ ) ₂ -COEt 12-52 2,6-Me ₂ Me-(CH ₂ ) ₂ -CH (NMe ₂ )-(CH ₂ ) ₂ -COiPr 12 -53 2,6-Me ₂ Me-(CH ₂ ) ₂ -CH (NMe ₂ )-(CH ₂ ) ₂ -COcPr 12-54 2,6-Me ₂ Me-(CH ₂ ) ₂ -CH (NMe ₂ )-(CH ₂ ) ₂ -CO ₂ Me 12-55 2,6-Me ₂ Me-(CH ₂ ) ₂ -CH (NMe ₂ )-(CH ₂ ) ₂ -CO ₂ Et 12-56 2,6-Me ₂ Me-(CH ₂ ) ₂ -CH (NMe ₂ )-(CH ₂ ) ₂ -CH ₂ OEt 12- 57 2,6-Me ₂ Me-(CH ₂ ) ₂ -O- (CH ₂ ) ₂ -H 12 -58 2,6-Me ₂ Me-(CH ₂ ) ₂ -O- (CH ₂ ) ₂ -COMe 12-59 2,6-Me ₂ Me-(CH ₂ ) ₂ -O- (CH ₂ ) ₂ -COEt 12-60 2,6-Me ₂ Me-(CH ₂ ) ₂ -O- (CH ₂ ) ₂ -COiPr 12-61 2,6-Me ₂ Me-(CH ₂ ) ₂ -O- (CH ₂ ) ₂ -COcPr 12-62 2,6-Me ₂ Me-(CH ₂ ) ₂ -O- (CH _{2 ) 2 - CO 2 Me 12-63 2,6} -Me 2 Me - (CH 2) 2 -O- (CH 2) 2 - CO 2 Et 12-64 2,6-Me 2 Me - (CH 2) 2 -O- (CH ₂ ) ₂ -CH ₂ OEt 12-65 2,6-Me ₂ Me-(CH ₂ ) ₂ -S- (CH ₂ ) ₂ -H 12-66 2,6-Me ₂ Me-( CH ₂ ) ₂ -S- (CH ₂ ) ₂ -COMe 12-67 2,6-Me ₂ Me-(CH ₂ ) ₂ -S- (CH ₂ ) ₂ -COEt 12-68 2,6-Me ₂ Me -(CH ₂ ) ₂ -S- (CH ₂ ) ₂ -COiPr 12-69 2,6-Me ₂ Me-(CH ₂ ) ₂ -S- (CH ₂ ) ₂ -COcPr 12-70 2,6-Me _{2 Me - (CH 2) 2} -S- (CH 2) 2 - CO 2 Me 12-71 2,6-Me 2 Me - (CH 2) 2 -S- (CH 2) 2 - CO 2 Et 12- _{72 2,6-Me 2 Me - (} CH 2) 2 -S- (CH 2) 2 - CH 2 OEt 12-73 2,6-Me 2 Me - (CH 2) 2 -NMe- (CH 2) 2 -H 12-74 2,6-Me ₂ Me-(CH ₂ ) ₂ -NMe- (CH ₂ ) ₂ -COMe 12-75 2,6-Me ₂ Me-(CH ₂ ) ₂ -NMe- (CH ₂ ) ₂ -COEt 12-76 2,6-Me ₂ Me-(CH ₂ ) ₂ -NMe- (CH ₂ ) ₂ -COiPr 12 -77 2,6-Me ₂ Me-(CH ₂ ) ₂ -NMe- (CH ₂ ) ₂ -COcPr 12-78 2,6-Me ₂ Me-(CH ₂ ) ₂ -NMe- (CH ₂ ) _2- CO ₂ Me 12-79 2,6-Me ₂ Me-(CH ₂ ) ₂ -NMe- (CH ₂ ) ₂ -CO ₂ Et 12-80 2,6-Me ₂ Me-(CH ₂ ) ₂ -NMe- (CH ₂ ) ₂ -CH ₂ OEt 12-81 2,6-Me ₂ Me-(CH ₂ ) ₂ -CH (OCH ₂ OEt)-(CH ₂ ) ₂ -H 12-82 2,6-Me ₂ Me -(CH ₂ ) ₂ -CH (OCH ₂ OEt)-(CH ₂ ) ₂ -COMe 12-83 2,6-Me ₂ Me-(CH ₂ ) ₂ -CH (OCH ₂ OEt)-(CH ₂ ) ₂ -COEt 12-84 2,6-Me ₂ Me-(CH ₂ ) ₂ -CH (OCH ₂ OEt)-(CH ₂ ) ₂ -COiPr 12-85 2,6-Me ₂ Me-(CH ₂ ) _2- CH (OCH ₂ OEt)-(CH ₂ ) ₂ -COcPr 12-86 2,6-Me ₂ Me-(CH ₂ ) ₂ -CH (OCH ₂ OEt)-(CH ₂ ) ₂ -CO ₂ Me 12-87 2,6-Me ₂ Me-(CH ₂ ) ₂ -CH (OCH ₂ OEt)-(CH ₂ ) ₂ -CO ₂ Et 12-88 2,6-Me ₂ Me-(CH ₂ ) ₂ -CH (OCH ₂ OEt)-(CH ₂ ) ₂ -CH ₂ OEt 12-89 2,6-Me ₂ Me-(CH ₂ ) ₂ -CH (O (CH ₂ ) ₂ OMe)-(CH ₂ ) ₂ -H 12- 90 2,6-Me ₂ Me-(CH ₂ ) ₂ -CH (O (CH ₂ ) ₂ OMe)-(CH ₂ ) ₂ -COMe 12-91 2,6-Me ₂ Me-(CH ₂ ) _2- CH (O (CH ₂ ) ₂ OMe)-(CH ₂ ) _2- COEt 12-92 2,6-Me ₂ Me-(CH ₂ ) ₂ -CH (O (CH ₂ ) ₂ OMe)-(CH ₂ ) ₂ -COiPr 12-93 2,6-Me ₂ Me-(CH ₂ ) ₂ -CH (O (CH ₂ ) ₂ OMe)-(CH ₂ ) ₂ -COcPr 12-94 2,6-Me ₂ Me-(CH ₂ ) ₂ -CH (O (CH ₂ ) ₂ OMe)-( _{CH 2) 2 - CO 2 Me} 12-95 2,6-Me 2 Me - (CH 2) 2 -CH (O (CH 2) 2 OMe) - (CH 2) 2 - CO 2 Et 12-96 2, 6-Me ₂ Me-(CH ₂ ) ₂ -CH (O (CH ₂ ) ₂ OMe)-(CH ₂ ) ₂ -CH ₂ OEt 12-97 2,6-Me ₂ Me-(CH ₂ ) ₂ -C (= N-OMe)-(CH ₂ ) ₂ -H 12-98 2,6-Me ₂ Me-(CH ₂ ) ₂ -C (= N-OMe)-(CH ₂ ) ₂ -COMe 12-99 2 , 6-Me ₂ Me-(CH ₂ ) ₂ -C (= N-OMe)-(CH ₂ ) ₂ -COEt 12-100 2,6-Me ₂ Me-(CH ₂ ) ₂ -C (= N- OMe)-(CH ₂ ) ₂ -COiPr 12-101 2,6-Me ₂ Me-(CH ₂ ) ₂ -C (= N-OMe)-(CH ₂ ) ₂ -COcPr 12-102 2,6-Me ₂ Me-(CH ₂ ) ₂ -C (= N-OMe)-(CH ₂ ) ₂ -CO ₂ Me 12-103 2,6-Me ₂ Me-(CH ₂ ) ₂ -C (= N-OMe) -(CH ₂ ) ₂ -CO ₂ Et 12-104 2,6-Me ₂ Me-(CH ₂ ) ₂ -C (= N-OMe)-(CH ₂ ) ₂ -CH ₂ OEt 12-105 2,6 -Me ₂ Me-(CH ₂ ) ₂ -C (-O (CH ₂ ) ₂ O-)-(CH ₂ ) ₂ -H 12-106 2,6-Me ₂ Me-(CH ₂ ) ₂ -C ( -O (CH ₂ ) ₂ O-)-(CH ₂ ) ₂ -COMe 12-107 2,6-Me ₂ Me-(CH ₂ ) ₂ -C (-O (CH ₂ ) ₂ O-)-(CH _Two ) ₂ -COEt 12-108 2,6-Me ₂ Me-(CH ₂ ) ₂ -C (-O (CH ₂ ) ₂ O-)-(CH ₂ ) ₂ -COiPr 12-109 2,6-Me ₂ Me-(CH ₂ ) ₂ -C (-O (CH ₂ ) ₂ O-)-(CH ₂ ) ₂ -COcPr 12-110 2,6-Me ₂ Me-(CH ₂ ) ₂ -C (-O ( CH ₂ ) ₂ O-)-(CH ₂ ) ₂ -CO ₂ Me 12-111 2,6-Me ₂ Me-(CH ₂ ) ₂ -C (-O (CH ₂ ) ₂ O-)-(CH ₂ ) ₂ -CO ₂ Et 12-112 2,6-Me ₂ Me-(CH ₂ ) ₂ -C (-O (CH ₂ ) ₂ O-)-(CH ₂ ) ₂ -CH ₂ OEt 12-113 2, 6-Me ₂ Me-(CH ₂ ) ₂ -C (-O (CH ₂ ) ₂ O-)-(CH ₂ ) ₂ -H 12-114 2,6-Me ₂ Me-(CH ₂ ) ₂ -C (-O (CH ₂ ) ₃ O-)-(CH ₂ ) ₂ -COMe 12-115 2,6-Me ₂ Me-(CH ₂ ) ₂ -C (-O (CH ₂ ) ₃ O-)-( CH ₂ ) ₂ -COEt 12-116 2,6-Me ₂ Me-(CH ₂ ) ₂ -C (-O (CH ₂ ) ₃ O-)-(CH ₂ ) ₂ -COiPr 12-117 2,6- Me ₂ Me-(CH ₂ ) ₂ -C (-O (CH ₂ ) ₃ O-)-(CH ₂ ) ₂ -COcPr 12-118 2,6-Me ₂ Me-(CH ₂ ) ₂ -C (- O (CH ₂ ) ₃ O-)-(CH ₂ ) ₂ -CO ₂ Me 12-119 2,6-Me ₂ Me-(CH ₂ ) ₂ -C (-O (CH ₂ ) ₃ O-)-( CH ₂ ) ₂ -CO ₂ Et 12-120 2,6-Me ₂ Me-(CH ₂ ) ₂ -C (-O (CH ₂ ) ₃ O-)-(CH ₂ ) ₂ -CO ₂ Et 12-121 2,6-Me ₂ Me-(CH ₂ ) ₂ -C (-O (CH ₂ ) ₃ O-)-(CH ₂ ) ₂ -CH ₂ OEt 12-122 2,6-Me ₂ Et-(CH ₂ ) ₂ -CH (OCH ₂ OEt)-(CH ₂ ) ₂ -H 12-123 2,6-Me ₂ Et-(CH ₂ ) ₂ -CH (OCH ₂ OEt)-(CH ₂ ) ₂ -COMe 12-124 2,6-Me _{2 Et - (CH 2) 2 -CH} (OCH 2 OEt) - (CH 2) 2 - COEt 12-125 2,6-Me 2 Et - (CH 2) 2 -CH (OCH 2 OEt) - (CH 2) ₂ -COiPr 12-126 2,6-Me ₂ Et-(CH ₂ ) ₂ -CH (OCH ₂ OEt)-(CH ₂ ) ₂ -COcPr 12-127 2,6-Me ₂ Et-(CH ₂ ) ₂ -CH (OCH ₂ OEt)-(CH ₂ ) ₂ -CO ₂ Me 12-128 2,6-Me ₂ Et-(CH ₂ ) ₂ -CH (OCH ₂ OEt)-(CH ₂ ) ₂ -CO ₂ Et 12-129 2,6-Me ₂ Et-(CH ₂ ) ₂ -CH (OCH ₂ OEt)-(CH ₂ ) ₂ -CH ₂ OEt 12-130 2,6-Me ₂ Et-(CH ₂ ) _2- CH (O (CH ₂ ) ₂ OMe)-(CH ₂ ) ₂ -H 12-131 2,6-Me ₂ Et-(CH ₂ ) ₂ -CH (O (CH ₂ ) ₂ OMe)-(CH ₂ ) ₂ -COMe 12-132 2,6-Me ₂ Et-(CH ₂ ) ₂ -CH (O (CH ₂ ) ₂ OMe)-(CH ₂ ) ₂ -COEt 12-133 2,6-Me ₂ Et-( CH ₂ ) ₂ -CH (O (CH ₂ ) ₂ OMe)-(CH ₂ ) ₂ -COiPr 12-134 2,6-Me ₂ Et-(CH ₂ ) ₂ -CH (O (CH ₂ ) ₂ OMe) _{- (CH 2) 2 - COcPr} 12-135 2,6-Me 2 Et - (CH 2) 2 -CH (O (CH 2) 2 OMe) - (CH 2) 2 - CO 2 Me 12-136 2, 6-Me ₂ Et-(CH ₂ ) ₂ -CH (O (CH ₂ ) ₂ OMe)-(CH ₂ ) ₂ -CO ₂ Et 12-137 2,6-Me ₂ Et-(CH ₂ ) ₂ -CH (O (CH ₂ ) ₂ OMe)-(CH ₂ ) _2- CH ₂ OEt 12-138 2,6-Me ₂ Et-(CH ₂ ) ₂ -C (= N-OMe)-(CH ₂ ) ₂ -H 12-139 2,6-Me ₂ Et-(CH ₂ ) ₂ -C (= N-OMe)-(CH ₂ ) ₂ -COMe 12-140 2,6-Me ₂ Et-(CH ₂ ) ₂ -C (= N-OMe)-(CH ₂ ) ₂ -COEt 12 -141 2,6-Me ₂ Et-(CH ₂ ) ₂ -C (= N-OMe)-(CH ₂ ) ₂ -COiPr 12-142 2,6-Me ₂ Et-(CH ₂ ) ₂ -C ( = N-OMe)-(CH ₂ ) ₂ -COcPr 12-143 2,6-Me ₂ Et-(CH ₂ ) ₂ -C (= N-OMe)-(CH ₂ ) ₂ -CO ₂ Me 12-144 2,6-Me ₂ Et-(CH ₂ ) ₂ -C (= N-OMe)-(CH ₂ ) ₂ -CO ₂ Et 12-145 2,6-Me ₂ Et-(CH ₂ ) ₂ -C ( = N-OMe)-(CH ₂ ) ₂ -CH ₂ OEt 12-146 2,6-Me ₂ Et-(CH ₂ ) ₂ -C (-O (CH ₂ ) ₂ O-)-(CH ₂ ) ₂ -H 12-147 2,6-Me ₂ Et-(CH ₂ ) ₂ -C (-O (CH ₂ ) ₂ O-)-(CH ₂ ) ₂ -COMe 12-148 2,6-Me ₂ Et- (CH ₂ ) ₂ -C (-O (CH ₂ ) ₂ O-)-(CH ₂ ) ₂ -COEt 12-149 2,6-Me ₂ Et-(CH ₂ ) ₂ -C (-O (CH ₂ ) ₂ O-)-(CH ₂ ) ₂ -COiPr 12-150 2,6-Me ₂ Et-(CH ₂ ) ₂ -C (-O (CH ₂ ) ₂ O-)-(CH ₂ ) ₂ -COcPr 12-151 2,6-Me ₂ Et-(CH ₂ ) ₂ -C (-O (CH ₂ ) ₂ O-)-(CH ₂ ) ₂ -CO ₂ Me 12-152 2,6-Me ₂ Et- (CH ₂ ) ₂ -C (-O (CH ₂ ) ₂ O-)-(CH ₂ ) ₂ -CO ₂ Et 12-153 2,6-Me ₂ Et-(CH ₂ ) ₂ -C (-O ( CH ₂ ) ₂ O-)-( CH ₂ ) ₂ -CH ₂ OEt 12-154 2,6-Me ₂ Et-(CH ₂ ) ₂ -C (-O (CH ₂ ) ₂ O-)-(CH ₂ ) ₂ -H 12-155 2, 6-Me ₂ Et-(CH ₂ ) ₂ -C (-O (CH ₂ ) ₃ O-)-(CH ₂ ) ₂ -COMe 12-156 2,6-Me ₂ Et-(CH ₂ ) ₂ -C (-O (CH ₂ ) ₃ O-)-(CH ₂ ) ₂ -COEt 12-157 2,6-Me ₂ Et-(CH ₂ ) ₂ -C (-O (CH ₂ ) ₃ O-)-( CH ₂ ) ₂ -COiPr 12-158 2,6-Me ₂ Et-(CH ₂ ) ₂ -C (-O (CH ₂ ) ₃ O-)-(CH ₂ ) ₂ -COcPr 12-159 2,6- Me ₂ Et-(CH ₂ ) ₂ -C (-O (CH ₂ ) ₃ O-)-(CH ₂ ) ₂ -CO ₂ Me 12-160 2,6-Me ₂ Et-(CH ₂ ) ₂ -C (-O (CH ₂ ) ₃ O-)-(CH ₂ ) ₂ -CO ₂ Et 12-161 2,6-Me ₂ Et-(CH ₂ ) ₂ -C (-O (CH ₂ ) ₃ O-) -(CH ₂ ) ₂ -CO ₂ Et 12-162 2,6-Me ₂ Et-(CH ₂ ) ₂ -C (-O (CH ₂ ) ₃ O-)-(CH ₂ ) ₂ -CH ₂ OEt ─中 Among the above exemplified compounds, preferred compounds are 1-13, 1-
19, 1-22, 1-24, 1-26, 1-33, 1-
35, 1-38, 1-39, 1-40, 1-41, 1-
42, 1-49, 1-51, 1-54, 1-71, 1-
74, 1-75, 1-76, 1-78, 1-83, 1-
84, 1-86, 1-87, 1-88, 1-90, 1-
91, 1-92, 1-99, 1-105, 1-111,
1-112, 1-123, 1-128, 1-130, 1
-135, 1-136, 1-137, 1-138, 1-
139, 1-140, 1-143, 1-144, 1-1
46, 1-147, 1-148, 1-151, 1-15
2, 1-154, 1-155, 1-156, 1-15
8, 1-159, 1-160, 1-166, 1-16
7, 1-168, 1-169, 1-171, 1-19
2, 1-299, 1-321, 1-390, 1-39
1,1-392,1-393,1-394,1-39
5, 1-396, 1-397, 1-398, 1-39
9, 1-400, 1-410, 1-411, 1-41
2, 1-414, 1-415, 1-416, 1-41
7, 1-418, 1-419, 1-420, 1-42
1, 1-425, 1-426, 1-427, 1-42
9, 1-430, 1-431, 1-432, 1-43
3, 1-435, 1-440, 1-441, 1-44
2, 1-443, 1-444, 1-445, 1-44
7, 1-448, 1-449, 1-450, 1-45
1, 1-456, 1-457, 1-458, 1-45
9, 1-460, 1-462, 1-463, 1-46
6, 1-467, 1-473, 2-3, 2-5, 2-
6, 2-8, 2-9, 2-11, 2-12, 2-14,
2-19, 2-20, 2-22, 2-23, 2-24,
2-25, 2-34, 2-66, 2-105, 2-10
7, 2-112, 2-137, 2-142, 2-17
8, 2-194, 2-371, 2-393, 2-42
6, 2-507, 2-509, 2-510, 2-51
3, 2-556, 4-104, 4-107, 4-39
9, 4-400, 4-401, 4-402, 4-40
3, 4-404, 4-405, 4-406, 4-40
7, 4-408, 4-410, 4-411, 4-41
4, 4-415, 4-416, 4-418, 5-67,
5-70, 6-4, 6-41, 10-1, 10-13
9, 10-146, 10-147, 10-148, 10
-149, 10-150, 10-151, 10-15
3, 10-154, 10-155, 10-156, 10
-157, 10-158, 10-159, 10-16
0, 10-161, 10-162, 10-163, 10
-166, 10-167, 10-168, 10-16
9, 10-171, 10-172, 10-173, 10
-174, 10-175, 10-176, 10-17
8, 10-179, 10-180, 10-185, 10
-187, 10-198, 10-203, 10-20
9, 10-221, 10-222, 10-223, 10
-224, 10-225, 10-227, 10-22
8, 10-230, 10-231, 10-232, 10
-234, 10-235, 10-237, 10-23
8, 10-239, 10-240, 10-241, 10
-242, 10-243, 10-244, 10-24
6, 10-247, 10-248, 10-249, 10
-250, 10-251, 10-252, 10-25
3, 10-254, 10-256, 10-257, 10
-259, 10-262, 11-8, 11-9, 11-
12, 11-38, 11-39, 11-41, 11-4
3, 11-44, 11-46, 11-48, 11-4
9, 11-51, 11-57, 11-61, 11-6
4, 11-66, 11-67, 11-68 and 11-7
No. 0, more preferably 4-104, 4-
107, 4-399, 4-400, 4-401, 4-4
02, 4-403, 4-404, 4-405, 4-40
6, 4-407, 4-408, 4-410, 4-41
1, 4-414, 4-415, 4-416, 4-41
8, 5-67, 5-70, 6-4, 6-41, 10-1
46, 10-147, 10-148, 10-149, 1
0-155, 10-156, 10-159, 10-16
0, 10-167, 10-168, 10-171, 10
-176, 10-178, 10-179, 10-18
0, 10-238, 10-240, 10-256, 10
-259, 11-38, 11-39, 11-43, 11
-44, 11-48, 11-49, 11-66, 11-
Nos. 67 and 11-68, and even more preferably 4-403, 4-407, 4-410, 4-41
1, 4-415, 4-416, 4-418, 5-67,
5-70, 6-4, 6-41, 10-148, 10-1
49, 10-168, 10-179, 11-43, 11
-44, 11-48 and 11-49.

[0113]

BEST MODE FOR CARRYING OUT THE INVENTION The N-substituted dihydropyrrole derivative of the present invention can be produced by the following methods A to I.

In step A, the dihydropyrrole derivative represented by the general formula (Ia) of the present invention is produced by acylating the amino acid derivative represented by the general formula (IVa) and closing the ring, and further substituted with a hydroxyl group. By introducing a group,
This is a step of producing the N-substituted dihydropyrrole derivative represented by the general formula (Ib) of the present invention. (Step A)

[0115]

Embedded image In the above formula, R ² , R ³ , R ⁵ , X, A and n are as defined above, R ^1a is the same as R ¹ except for a hydrogen atom, and R ^4a is a hydrogen atom Other than R ⁴ ,
Y ¹ represents a hydroxyl group or a halogen atom (preferably a hydroxyl group, a chlorine atom or a bromine atom), and Z ¹ represents a halogen atom, a C ₁ -C ₆ alkylsulfonyl group or a phenylsulfonyl group (the phenylsulfonyl group) groups are the same or different (preferably showing a good.) which is substituted by 1 to 5 substituents selected from halogen atoms and C ₁ -C group consisting ₆ alkyl group, a chlorine atom, a methylsulfonyl group Phenylsulfonyl group or tolylsulfonyl group). (Step A-1) In step A-1, an amino acid derivative represented by the general formula (IVa) is reacted with a phenylacetic acid derivative represented by the general formula (IXa), and is represented by the general formula (IIa) This is a step of producing an N-acylamino acid derivative. (I) In this step, when Y ¹ in compound (IXa) is a hydroxyl group, compound (IVa) is reacted with corresponding compound (IXa) in an inert solvent in the presence of a base and a condensing agent, (IIa) can be produced.

The base to be used is not particularly limited as long as it usually shows a pH of 8 or more. For example, hydroxides of alkali metals such as sodium hydroxide and potassium hydroxide; Hydroxides of alkaline earth metals; carbonates of alkali metals such as sodium carbonate and potassium carbonate; bicarbonates of alkali metals such as sodium bicarbonate and potassium bicarbonate; such as sodium hydride and potassium hydride Metal hydrides; alkoxides such as sodium methoxide, sodium ethoxide and potassium tert-butoxide; organic bases such as triethylamine, N, N-dimethylaniline and pyridine; or methyllithium, butyllithium, methylmagnesium Bromide, lithium diisopro Ruamido like obtained an organic metals, etc., preferably an organic bases, more preferably a pyridine or triethylamine.

The amount of the base to be used depends on the amount of the compound (IVa)
The amount is usually 1.0 to 10.0 mol, preferably 1.0 to 5.0 mol, per 1 mol.

The condensing agent to be used is not particularly limited as long as it is a reagent capable of condensing. For example, C ₁ -C ₄ alkyl chloroformate such as methyl chloroformate and ethyl chloroformate; 2-chloro-1-iodide It may be a pyridinium salt such as methylpyridinium; or a carbodiimide such as dicyclohexylcarbodiimide, preferably a pyridinium salt, and more preferably 2-chloro-1-methylpyridinium iodide.

The amount of the condensing agent used depends on the amount of the compound (IV
a) It is usually 1.0 to 5.0 mol, preferably 1.0 to 2.0 mol, per 1 mol.

The solvent used is not particularly limited as long as it does not inhibit the reaction and dissolves the starting materials to some extent.
For example, ethers such as diethyl ether, dimethoxyethane, tetrahydrofuran and dioxane; aromatic hydrocarbons such as benzene, toluene, xylene and chlorobenzene; nitriles such as acetonitrile;
Amides such as N, N-dimethylformamide, N, N-dimethylacetamide and N-methyl-2-pyrrolidone; sulfoxides such as dimethylsulfoxide and sulfolane; halogenated hydrocarbons such as methylene chloride and chloroform; Esters such as ethyl acetate and ethyl propionate; aliphatic hydrocarbons such as hexane, cyclohexane and heptane; pyridines such as pyridine and picoline; or a mixed solvent thereof, preferably ether. , Halogenated hydrocarbons, esters, aliphatic hydrocarbons or aromatic hydrocarbons, more preferably tetrahydrofuran, methylene chloride, ethyl acetate or toluene.

The amount of the solvent used depends on the amount of the compound (IVa)
It is usually 1.0 to 20 liters per 1 mol,
Preferably, it is 1.0 to 10 liters.

The reaction temperature varies depending on the starting compound, reaction reagent, solvent and the like, but is usually from -40 ° C to 150 ° C, preferably from 0 to 100 ° C.

The reaction time varies depending on the starting compound, reaction reagent, solvent, reaction temperature and the like, but is usually 6 minutes to 48 hours, preferably 10 minutes to 24 hours. (Ii) In this step, when Y ¹ in compound (IXa) is a halogen atom, compound (IVa) is reacted with corresponding compound (IXa) in the presence of a base in an inert solvent to give compound (IIa) Can be manufactured.

The base to be used is not particularly limited as long as it usually shows a pH of 8 or more. For example, hydroxides of alkali metals such as sodium hydroxide and potassium hydroxide; Hydroxides of alkaline earth metals such as; carbonates of alkali metals such as sodium carbonate and potassium carbonate; bicarbonates of alkali metals such as sodium hydrogen carbonate and potassium hydrogen carbonate; sodium hydroxide and potassium hydride Metal hydrides; alkoxides such as sodium methoxide, sodium ethoxide and potassium tert-butoxide; organic bases such as triethylamine, N, N-dimethylaniline and pyridine; or methyllithium, butyllithium, methyl Magnesium bromide, lithium diisopro Ruamido like obtained an organic metals, etc., preferably, alkali metal carbonates, are bicarbonates or organic bases alkali metal, more preferably,
Sodium carbonate, sodium bicarbonate, pyridine or triethylamine.

The amount of the base to be used is determined based on the amount of compound (IXa)
The amount is usually 1.0 to 10.0 mol, preferably 1.0 to 5.0 mol, per 1 mol.

The solvent used is not particularly limited as long as it does not inhibit the reaction and dissolves the starting materials to some extent.
For example, ethers such as diethyl ether, dimethoxyethane, tetrahydrofuran and dioxane; aromatic hydrocarbons such as benzene, toluene, xylene and chlorobenzene; nitriles such as acetonitrile;
Amides such as N, N-dimethylformamide, N, N-dimethylacetamide and N-methyl-2-pyrrolidone; sulfoxides such as dimethylsulfoxide and sulfolane; halogenated hydrocarbons such as methylene chloride and chloroform; Esters such as ethyl acetate and ethyl propionate; aliphatic hydrocarbons such as hexane, cyclohexane and heptane; pyridines such as pyridine and picoline; or a mixed solvent thereof, preferably ether. , Halogenated hydrocarbons, esters, aliphatic hydrocarbons or aromatic hydrocarbons, more preferably tetrahydrofuran, ethyl acetate or toluene. In this step, a two-layer reaction may be performed using the water-insoluble solvent and water.

The amount of the solvent used is determined according to the amount of the compound (IXa)
It is usually 1.0 to 20 liters per 1 mol,
Preferably, it is 1.0 to 10 liters.

The reaction temperature varies depending on the starting compound, reaction reagent, solvent and the like, but is usually from -70 ° C to 150 ° C, preferably from 0 to 100 ° C.

The reaction time varies depending on the starting compound, reaction reagent, solvent, reaction temperature and the like, but is usually 6 minutes to 48 hours, preferably 10 minutes to 24 hours.

Compound (IVa) used in this step is
It is a known compound or a known method (for example, Tetrah
edron, 1981, 37, 4245, Tetrahedorn Letters, 1990,
31,991, Synthesis, 1987, 12, 1115 or J. Chem. So
c., 1965, 7179).

The compound (IX) used in this step
a) is commercially available or known method (for example, J. Am. Chem. Soc. 1950, 72, 4091 or J. Am. Che.
m. Soc. 1936, 58, 1233). (Step A-2) In step A-2, an N-acylamino acid derivative represented by the general formula (IIa) is reacted with a base in an inert solvent, and ring-closing is performed.
This is the step of manufacturing a).

The base used in this step is not particularly limited as long as it shows basic basicity. For example, hydroxides of alkali metals such as sodium hydroxide and potassium hydroxide; calcium hydroxide and Hydroxides of alkaline earth metals such as magnesium hydroxide; carbonates of alkali metals such as sodium carbonate and potassium carbonate; bicarbonates of alkali metals such as sodium bicarbonate and potassium bicarbonate; sodium hydride and Metal hydrides such as potassium hydride; alkoxides such as sodium methoxide, sodium ethoxide and potassium tert-butoxide; or organic metals such as methyllithium, butyllithium, methylmagnesium bromide and lithium diisopropylamide. And preferably metal hydride, alcohol A Sid acids or organic metals, more preferably, sodium methoxide or tert- butoxide.

The amount of the base to be used depends on the amount of the compound (IIa)
The amount is usually 1.0 to 10.0 mol, preferably 1.0 to 5.0 mol, per 1 mol.

The solvent used in this step is not particularly limited as long as it does not inhibit the reaction and dissolves the starting materials to some extent. For example, ethers such as diethyl ether, dimethoxyethane, tetrahydrofuran and dioxane; Aromatic hydrocarbons such as benzene, toluene, xylene and chlorobenzene; nitriles such as acetonitrile; amides such as N, N-dimethylformamide, N, N-dimethylacetamide and N-methyl-2-pyrrolidone; Sulfoxides such as dimethyl sulfoxide and sulfolane; halogenated hydrocarbons such as methylene chloride and chloroform; esters such as ethyl acetate and ethyl propionate; aliphatic hydrocarbons such as hexane, cyclohexane and heptane; pyridine And picolin Such pyridines; or a mixed solvent thereof, preferably ethers, esters, aliphatic hydrocarbons, amides or aromatic hydrocarbons, more preferably tetrahydrofuran or N, N, N
-Dimethylformamide.

The amount of the solvent used depends on the amount of the compound (IIa)
It is usually 1.0 to 20 liters per 1 mol,
Preferably, it is 1.0 to 10 liters.

The reaction temperature varies depending on the starting compound, the reaction reagent, the solvent and the like, but is usually from -40 ° C to 150 ° C, preferably from 0 to 100 ° C.

The reaction time varies depending on the starting compound, reaction reagent, solvent, reaction time and the like, but is usually 6 minutes to 48 hours, preferably 10 minutes to 24 hours. (Step A-3) In step A-3, a hydroxydihydropyrrole derivative represented by the general formula (Ia) is reacted with a compound represented by the general formula (Xa) in an inert solvent in the presence of a base, This is a step of producing the compound (Ib) of the present invention.

The base used in the present invention is not particularly limited as long as it usually shows a pH of 8 or more. For example, hydroxides of alkali metals such as sodium hydroxide and potassium hydroxide; Hydroxides of alkaline earth metals such as magnesium; carbonates of alkali metals such as sodium carbonate and potassium carbonate; bicarbonates of alkali metals such as sodium bicarbonate and potassium bicarbonate; sodium hydride and hydrogenation Metal hydrides such as potassium; alkoxides such as sodium methoxide, sodium ethoxide and potassium tert-butoxide; or triethylamine, N, N-
It can be an organic base such as dimethylaniline and pyridine, preferably an organic base, more preferably triethylamine or pyridine.

The amount of the base used is the same as that of compound (Ia) 1
It is usually 1.0 to 10.0 mol with respect to mol,
Preferably, it is 1.0 to 5.0 mol.

The solvent used is not particularly limited as long as it does not inhibit the reaction and dissolves the starting materials to some extent.
For example, ethers such as diethyl ether, dimethoxyethane, tetrahydrofuran and dioxane; aromatic hydrocarbons such as benzene, toluene, xylene and chlorobenzene; nitriles such as acetonitrile;
Amides such as N, N-dimethylformamide, N, N-dimethylacetamide and N-methyl-2-pyrrolidone; sulfoxides such as dimethylsulfoxide and sulfolane; halogenated hydrocarbons such as methylene chloride and chloroform; Esters such as ethyl acetate and ethyl propionate; aliphatic hydrocarbons such as hexane, cyclohexane and heptane; pyridines such as pyridine and picoline; or a mixed solvent thereof, preferably ether. , Halogenated hydrocarbons, esters, aliphatic hydrocarbons or aromatic hydrocarbons, more preferably tetrahydrofuran, methylene chloride, ethyl acetate or toluene.

The amount of the solvent used depends on the amount of the compound (Ia) 1
It is usually 1.0 to 20 liters, preferably 1.0 to 10 liters, based on mol.

The reaction temperature varies depending on the starting compound, reaction reagent, solvent and the like, but is usually from -40 ° C to 150 ° C, preferably from 0 to 100 ° C.

The reaction time varies depending on the starting compound, reaction reagent, solvent, reaction temperature and the like, but is usually from 6 minutes to 48 hours, preferably from 10 minutes to 24 hours.

In the step B, when the amino acid derivative represented by the general formula (IVb) is N-acylated and the O-substituted compound represented by the general formula (V) is by-produced, By converting into the N-substituted compound represented by the formula (Ia) and introducing a substituent into the hydroxyl group of the compound (IIa), an N-acylamino acid derivative represented by the general formula (IIa) which is an intermediate of the present invention is produced It is a process. (Step B)

[0145]

Embedded image In the above formula, R ^1a , R ² , R ³ , R ⁵ , A and n are as defined above, and Y ² is a hydroxyl group or a halogen atom (preferably a hydroxyl group, a chlorine atom or a bromine atom. Yes.), Z
² is a halogen atom, a C ₁ -C ₆ alkylsulfonyl group or a phenylsulfonyl group (the phenylsulfonyl group is 1 to 5 carbon atoms selected from the same or different halogen atoms and C _{1 to} C ₆ alkyl groups) (Preferably a chlorine atom, a methylsulfonyl group, a phenylsulfonyl group or a tolylsulfonyl group). (Step B-1) In the step B-1, a hydroxylamine derivative represented by the general formula (IVb) is reacted with a phenylacetic acid derivative represented by the general formula (IXb) to obtain a compound represented by the general formula (II)
This is a step of producing the intermediate of the present invention represented by b).

This step can be performed according to step A-1.

The compound (IVb) used in this step is
It is a known compound or a known method (for example, Libigs
Ann. Chem., 1981, 34 , 1378; Chem. Ber., 1901, 34 ,
1867, J. Chem. Soc., 1959, 2049 or Chem. Ber., 19
55, 88 , 38).

In this step, an O-acyl compound represented by the general formula (V) may be obtained as a by-product in some cases, for example, according to the method described in Angew. Chem., 1988, 100 , 965. And compound (IIb). (Step B-2) In the step B-2, the N-hydroxy compound represented by the general formula (IIb) is converted into an inert solvent in the presence of a base.
This is a step of producing a compound (IIa) which is an intermediate of the present invention by reacting with a compound represented by the general formula (Xb).

The base used in the present invention is not particularly limited as long as it usually has a pH of 8 or more. For example, hydroxides of alkali metals such as sodium hydroxide and potassium hydroxide; Hydroxides of alkaline earth metals such as magnesium; carbonates of alkali metals such as sodium carbonate and potassium carbonate; bicarbonates of alkali metals such as sodium bicarbonate and potassium bicarbonate; sodium hydride and hydrogenation Metal hydrides such as potassium; alkoxides such as sodium methoxide, sodium ethoxide and potassium tert-butoxide; or triethylamine, N, N-
It can be an organic base such as dimethylaniline and pyridine, preferably metal hydrides, alkoxides and organic bases, more preferably sodium hydride or triethylamine.

The amount of the base used is determined according to the amount of the compound (IIb)
It is usually 1.0 to 5.0 mol per 1 mol,
Preferably, it is 1.0 to 2.0 mol.

The solvent used is not particularly limited as long as it does not inhibit the reaction and dissolves the starting materials to some extent.
For example, ethers such as diethyl ether, dimethoxyethane, tetrahydrofuran and dioxane; aromatic hydrocarbons such as benzene, toluene, xylene and chlorobenzene; nitriles such as acetonitrile;
Amides such as N, N-dimethylformamide, N, N-dimethylacetamide and N-methyl-2-pyrrolidone; sulfoxides such as dimethylsulfoxide and sulfolane; halogenated hydrocarbons such as methylene chloride and chloroform; Esters such as ethyl acetate and ethyl propionate; aliphatic hydrocarbons such as hexane, cyclohexane and heptane; pyridines such as pyridine and picoline; or a mixed solvent thereof, preferably ether. , Halogenated hydrocarbons, esters, aliphatic hydrocarbons or aromatic hydrocarbons, more preferably tetrahydrofuran, methylene chloride, ethyl acetate or toluene.

The amount of the solvent used is determined according to the amount of the compound (IIb)
It is usually 1.0 to 20 liters per 1 mol,
Preferably, it is 1.0 to 10 liters.

The reaction temperature varies depending on the starting compound, reaction reagent, solvent and the like, but is usually from -40 ° C to 150 ° C, preferably from 0 to 100 ° C.

The reaction time varies depending on the starting compound, reaction reagent, solvent, reaction temperature and the like, but is usually 6 minutes to 48 hours, preferably 10 minutes to 24 hours.

The compound (Ia) of the present invention can be produced by continuously performing the step A-2 without isolating the compound (IIa).

In the step C, the hydroxylamine derivative represented by the general formula (VI) is N-acylated, and when R ¹ in the starting compound (VI) is hydrogen, the general formula (VII)
When the O-substituted product represented by
This is a step of producing a compound (II), which is an intermediate of the present invention, by converting into the corresponding N-substituted compound represented by I) and further introducing a substituent into a hydroxyl group as required. (Step C)

[0157]

Embedded image In the above formula, R ¹ , R ² , R ³ , R ⁵ , A and n have the same meanings as described above, and Y ³ represents a hydroxyl group or a halogen atom (preferably a hydroxyl group, a chlorine atom or a bromine atom. is there.). (Step C-1) Step C-1 comprises reacting a hydroxylamine derivative represented by the general formula (VI) with a phenylacetic acid derivative represented by the general formula (IXc),
This is a step of producing the intermediate of the present invention represented by I).

This step can be performed according to step B-1.

The compound (VI) used in this step is a known compound or a known method (for example, Chem. Be.
r., 1913, 46 , 99, Chem. Ber., 1955, 88 , 38 or J.O.
rg. Chem., 1958, 23 , 964).

In this step, when R ¹ is hydrogen, an O-acyl compound represented by the general formula (VII) may be obtained as a by-product in some cases. For example, Angew. Chem., 1988
100 , 965, and can be converted to compound (III). (Step C-2) Step C-2 is a step of producing compound (II) of the present invention by reacting compound (III) with an acid and an alcohol.

The acid used in this step is not particularly restricted but includes, for example, mineral acids such as hydrochloric acid, sulfuric acid, perchloric acid and nitric acid; carboxylic acids such as formic acid, acetic acid and propionic acid; methanesulfonic acid Sulfonic acids such as benzenesulfonic acid and p-toluenesulfonic acid monohydrate; acid addition salts of amines such as pyridine hydrochloride and triethylamine hydrochloride; or aluminum chloride, titanium tetrachloride, zinc chloride, odor. It can be a metal halide such as magnesium fluoride and a Lewis acid such as boron trifluoride etherate, preferably sulfonic acids.

The amount of the acid used is determined according to the compound (III) 1
It is usually from 1.0 to 100 mol, preferably from 1.0 to 50 mol, per mol.

The alcohol used in this step is an alcohol represented by the formula R ⁵ OH (wherein R ⁵ has the same meaning as described above), for example, methanol, ethanol, propanol or butanol. And preferably methanol or ethanol.

The amount of the alcohol to be used is generally 1 to 100 mol, preferably 1 to 50 mol, per 1 mol of compound (III).

This step can be performed in the presence of a solvent. The solvent used is not particularly limited as long as it does not inhibit the reaction and dissolves the starting material to some extent.
Ethers such as diethyl ether, dimethoxyethane, tetrahydrofuran and dioxane; aromatic hydrocarbons such as benzene, toluene, xylene and chlorobenzene; nitriles such as acetonitrile;
Amides such as dimethylformamide, N, N-dimethylacetamide and N-methyl-2-pyrrolidone; sulfoxides such as dimethylsulfoxide and sulfolane; halogenated hydrocarbons such as methylene chloride and chloroform; ethyl acetate and propion Esters such as ethyl acid; aliphatic hydrocarbons such as hexane, cyclohexane and heptane; or a mixed solvent thereof, preferably ethers, halogenated hydrocarbons, and aliphatic hydrocarbons. Or aromatic hydrocarbons, more preferably tetrahydrofuran, methylene chloride, dichloroethane, chloroform or toluene.

The amount of the solvent to be used depends on the amount of the compound (III)
It is usually 0.1 to 20 liters per 1 mol,
Preferably, it is 0.1 to 10 liters.

The reaction temperature varies depending on the starting compound, the reaction reagent, the solvent and the like, but is usually from -40 ° C to 150 ° C, preferably from 0 to 100 ° C.

The reaction time varies depending on the starting compound, reaction reagent, solvent, reaction temperature and the like, but is usually 6 minutes to 48 hours, preferably 10 minutes to 24 hours.

In the step D, the compound (Ib) of the present invention is obtained by exchanging the O-substituent of the N-substituted dihydropyrrole derivative of the compound of the present invention represented by the general formula (Ic) with another substituent. This is the manufacturing process. (Step D)

[0170]

Embedded image In the above formula, R ^1a , R ² , R ³ , R ⁴ , A and n are as defined above, and R ^1b is a C ₁ -C ₆ alkoxymethyl group, (C
₁ -C ₆ alkoxy) C ₁ -C ₆ alkoxy represents a methyl group or a phenoxymethyl group (preferably methoxymethyl,
Ethoxymethyl or phenoxymethyl. ), Z ³
Is a halogen atom, a C ₁ -C ₆ alkylsulfonyl group or a phenylsulfonyl group (the phenylsulfonyl group is
By 1 to 5 substituents selected from the same or different halogen atoms and C ₁ -C group consisting ₆ alkyl group may be substituted. (Preferably a chlorine atom, a methylsulfonyl group, a phenylsulfonyl group or a tolylsulfonyl group). (Step D-1) Step D-1 comprises reacting the compound represented by the general formula (Ic) with a compound having an affinity for an acid or an oxygen atom in an inert solvent to give the compound of the present invention (I
This is the step of manufacturing d).

The solvent used is not particularly limited as long as it does not inhibit the reaction and dissolves the starting materials to some extent.
For example, alcohols such as methanol, ethanol, ethylene glycol and glycerin; ethers such as diethyl ether, dimethoxyethane, tetrahydrofuran and dioxane; aromatic hydrocarbons such as benzene, toluene, xylene and chlorobenzene; acetonitrile. Amides such as N, N-dimethylformamide, N, N-dimethylacetamide and N-methyl-2-pyrrolidone; sulfoxides such as dimethylsulfoxide and sulfolane; halogenations such as methylene chloride and chloroform Hydrocarbons;
Esters such as ethyl acetate and ethyl propionate; aliphatic hydrocarbons such as hexane, cyclohexane and heptane; fatty acid carboxylic acids such as acetic acid;
Water; or a mixed solvent thereof, preferably halogenated hydrocarbons, alcohols or ethers, more preferably dichloromethane, methanol or ethanol.

The amount of the solvent used depends on the amount of the compound (Ic)
It is usually 1.0 to 20.0 liters, preferably 1.0 to 10.0 liters, based on mol.

The acid used is not particularly restricted but includes, for example, mineral acids such as hydrochloric acid, sulfuric acid, perchloric acid and nitric acid; carboxylic acids such as formic acid, acetic acid and propionic acid; methanesulfonic acid, benzenesulfonic acid Acid and sulfonic acids such as p-toluenesulfonic acid monohydrate; acid addition salts of amines such as pyridine hydrochloride and triethylamine hydrochloride; or aluminum chloride, titanium tetrachloride, zinc chloride, magnesium bromide. A metal halide and a Lewis acid such as boron trifluoride etherate,
Preferably, they are sulfonic acids.

The amount of the acid to be used is as follows: 1 m of compound (Ic)
The amount is usually 1.0 to 100 mol, and preferably 1.0 to 50 mol, based on ol.

Compounds having an affinity for an oxygen atom include, for example, trimethylsilane iodide, trimethylsilane bromide,
Halogenated silanes such as trimethylsilane chloride; silylsulfonates such as trimethylsilyltrifluoromethanesulfonate and trimethylsilylsulfonate chloride;
Alternatively, it may be a silyl perchloric acid such as trimethylsilyl perchloric acid, preferably trimethylsilane bromide.

The amount of the compound having an affinity for an oxygen atom to be used is usually 1.0 to 1 mol of the compound (Ic).
１10.0 mol, preferably 1.0 to 5.0 m
ol.

The reaction temperature varies depending on the starting compound, reaction reagent, solvent and the like, but is usually from -10 ° C to 150 ° C, preferably from room temperature to 150 ° C.

The reaction time varies depending on the starting compound, reaction reagent, solvent, reaction temperature and the like, but is usually 6 minutes to 48 hours, preferably 10 minutes to 24 hours. (Step D-2) In the step D-2, the compound of the present invention (Ib) is reacted with the compound represented by the general formula (Xc) in an inert solvent in the presence of a base. This is the manufacturing process.

This step can be performed according to step B-2.

Step E comprises adding an N-unsubstituted dihydropyrrole derivative represented by the general formula (VIII) to an inert solvent
This is a step of producing the compound (Ie) of the present invention by reacting the compound represented by the general formula (XI) in the presence of a base to introduce a sulfur functional group into the nitrogen atom of the dihydropyrrole ring. (Step E)

[0181]

Embedded image In the above formula, R ² , R ³ , R ⁴ , A and n have the same meanings as described above, and R ^1c has the same meaning as R ¹ except for a hydrogen atom,
Q is a halogen atom, a C ₁ -C ₆ alkylsulfonyl group,
A phenylsulfonyl group (the phenylsulfonyl group is
By 1 to 5 substituents selected from the same or different halogen atoms and C ₁ -C group consisting ₆ alkyl group may be substituted. ) Or general formula

[0182]

Embedded image (Wherein, R ⁷ and R ⁸ each independently represent a hydrogen atom, a halogen atom or a C ₁ -C ₆ alkyl group, or together with a carbon atom to which they are attached, form a benzene ring or A cyclohexene ring) (preferably, R ⁷ and R ⁸ together with the carbon atom to which they are attached are a benzene ring).

The base to be used is not particularly limited as long as it usually shows a pH of 8 or more. For example, hydroxides of alkali metals such as sodium hydroxide and potassium hydroxide; Hydroxides of alkaline earth metals; carbonates of alkali metals such as sodium carbonate and potassium carbonate; bicarbonates of alkali metals such as sodium bicarbonate and potassium bicarbonate; such as sodium hydride and potassium hydride Metal hydrides; alkoxides such as sodium methoxide, sodium ethoxide and potassium tert-butoxide; or organic bases such as triethylamine, N, N-dimethylaniline and pyridine;
Preferably, it is an alkali metal hydroxide or an alkali metal carbonate, and more preferably, sodium hydroxide, potassium carbonate or sodium carbonate.

The amount of the base used is usually the same as that of the compound (V
III) It is 1.0 to 10.0 mol, preferably 1.0 to 5.0 mol, per 1 mol.

The solvent used is not particularly limited as long as it does not inhibit the reaction and dissolves the starting materials to some extent.
For example, alcohols such as methanol, ethanol, ethylene glycol and glycerin; ethers such as diethyl ether, dimethoxyethane, tetrahydrofuran and dioxane; ketones such as acetone, methyl ethyl ketone; benzene, toluene, xylene and chlorobenzene. Aromatic hydrocarbons; nitriles such as acetonitrile; N, N-dimethylformamide, N, N-dimethylacetamide and N-methyl-2
Amides such as pyrrolidone; sulfoxides such as dimethylsulfoxide and sulfolane; halogenated hydrocarbons such as methylene chloride and chloroform; esters such as ethyl acetate and ethyl propionate; such as hexane, cyclohexane and heptane. Aliphatic hydrocarbons; fatty acid carboxylic acids such as acetic acid; water; or a mixed solvent thereof, preferably halogenated hydrocarbons, ethers, esters or ketones, more preferably Is dichloromethane, ethyl acetate or acetone.

The amount of the solvent to be used depends on the amount of the compound (VII)
I) The amount is usually 1.0 to 20.0 liters, preferably 1.0 to 10 liters, per 1 mol.

The reaction temperature varies depending on the starting compound, reaction reagent, solvent and the like, but is usually from -40 ° C to 150 ° C, preferably from 0 to 100 ° C.

The reaction time varies depending on the starting compound, reaction reagent, solvent, reaction temperature and the like, but is usually 6 minutes to 48 hours, preferably 10 minutes to 24 hours.

Compound (VIII) used in this step
Can be produced, for example, according to the method described in JP-A-4-226957.

The compound (XI) used in this step is a known compound or a known method (for example, J. Med,
Chem., 1993, 36 , 912, J. Org.Chem., 1966, 31 , 248
4 or the method described in J. Org. Chem., 1969, 51 , 55)
It can be prepared according to

In step F, the N-sulfur-containing functional group-substituted dihydropyrrole derivative of the present invention represented by the general formula (Ie) is
This is a step of producing a compound of the present invention represented by the general formula (If) by oxidizing a sulfur atom using an oxidizing agent in an inert solvent. (Step F)

[0192]

Embedded image In the above formula, R ^1c , R ² , R ³ , R ⁴ , A and n have the same meanings as described above, and m represents 1 or 2.

The oxidizing agent used in this step is not particularly limited as long as it is an ordinary oxidizing agent for a sulfur atom, and examples thereof include hydrogen peroxide, m-chloroperbenzoic acid, sodium periodate and oxone (peroxo). Potassium hydrogensulfate-containing substances, peroxides such as E.I. Dupont (registered trademark); halogenating agents such as N-chlorosuccinimide; hypochlorites such as sodium hypochlorite; or oxygen And is preferably a peroxide, more preferably hydrogen peroxide or m-chloroperbenzoic acid.

The amount of the oxidizing agent to be used depends on the amount of the compound (Ie)
Usually, it is 1.0 to 10.0 mol with respect to 1 mol. When n is 1, it is preferably 1.0 to 1.5 mol. When n is 2, it is preferably 2.0 to 10.0 mol. 5.0mol
It is.

When hydrogen peroxide is used as the oxidizing agent,
This step can be oxidized in the presence of a catalyst.

The catalyst used can be, for example, sodium tungstate.

The amount of the catalyst to be used depends on the amount of the compound (Ie) 1
It is usually 0.001 to 0.5 mol, preferably 0.001 to 0.2 mol, based on mol.

The solvent used is not particularly limited as long as it does not inhibit the reaction and dissolves the starting materials to some extent.
For example, alcohols such as methanol, ethanol, ethylene glycol and glycerin; ethers such as diethyl ether, dimethoxyethane, tetrahydrofuran and dioxane; aromatic hydrocarbons such as benzene, toluene, xylene and chlorobenzene;
Amides such as -dimethylformamide, N, N-dimethylacetamide and N-methyl-2-pyrrolidone;
Sulfoxides such as dimethyl sulfoxide and sulfolane; halogenated hydrocarbons such as methylene chloride and chloroform; esters such as ethyl acetate and ethyl propionate; aliphatic hydrocarbons such as hexane, cyclohexane and heptane; pyridine And pyridines such as picoline; ketones such as acetone, methyl ethyl ketone and cyclohexanone; fatty acid carboxylic acids such as acetic acid; water; or a mixed solvent thereof, preferably ethers, halogenated hydrocarbons. Or esters, more preferably tetrahydrofuran,
Methylene chloride, dichloroethane or ethyl acetate.

The amount of the solvent used depends on the amount of the compound (Ie)
It is usually 1.0 to 20.0 liters, preferably 1.0 to 10.0 liters, based on mol.

The reaction temperature varies depending on the starting compound, reaction reagent, solvent and the like, but is usually from -20 ° C to 150 ° C, preferably from 10 to 100 ° C.

The reaction time varies depending on the starting compound, reaction reagent, solvent, reaction temperature and the like, but is usually 6 minutes to 48 hours, preferably 10 minutes to 24 hours.

Step G comprises reacting the O-halogenomethyl derivative of the present invention represented by the general formula (Ig) with an alcohol or thiol compound represented by the general formula (XII) in an inert solvent in the presence of a base. And producing a compound of the present invention represented by the general formula (Ih). (Step G)

[0203]

Embedded image In the above formula, R ² , R ³ , R ⁴ , A and n have the same meanings as described above, Y ⁴ represents a halogen atom (preferably a bromine atom or a chlorine atom), and Z ⁴ represents , An oxygen atom or a sulfur atom (preferably an oxygen atom), and R ⁹ is C ₁
-C ₆ alkyl group (the alkyl group may be substituted by 1 to 5 halogen atoms), C ₂ -C ₆ alkenyl group, (C ₁ -C ₆ alkoxy) C ₁ -C ₆ alkyl group or It represents a benzyl group (preferably a methyl group or an ethyl group).

The base to be used is not particularly limited as long as it usually shows a pH of 8 or more. Examples thereof include alkali metal carbonates such as sodium carbonate and potassium carbonate; and alkali metal carbonates such as sodium hydrogen carbonate and potassium hydrogen carbonate. Hydrides of alkali metals such as sodium hydride and potassium hydride; alkoxides such as sodium methoxide, sodium ethoxide and potassium tert-butoxide; triethylamine
Organic bases such as N, N-dimethylaniline and pyridine; or organic metals such as methyllithium and butyllithium, preferably hydrides, alkoxides or organic bases of alkali metals. , More preferably sodium hydride, triethylamine or potassium
tert-butoxide.

The amount of the base used is usually the same as that of the compound (I
g) It is 1.0 to 10.0 mol per 1 mol,
Preferably, it is 1.0 to 5.0 mol.

The solvent used is not particularly limited as long as it does not inhibit the reaction and dissolves the starting materials to some extent.
For example, alcohols such as methanol, ethanol, ethylene glycol and glycerin; ethers such as diethyl ether, dimethoxyethane, tetrahydrofuran and dioxane; aromatic hydrocarbons such as benzene, toluene, xylene and chlorobenzene;
Amides such as -dimethylformamide, N, N-dimethylacetamide and N-methyl-2-pyrrolidone;
Sulfoxides such as dimethyl sulfoxide and sulfolane; esters such as ethyl acetate and ethyl propionate; aliphatic hydrocarbons such as hexane, cyclohexane and heptane; pyridines such as pyridine;
Alternatively, these may be a mixed solvent, preferably ethers, amides or sulfoxides, more preferably N, N-dimethylformamide or tetrahydrofuran.

The amount of the solvent to be used depends on whether the compound (Ig) 1
It is usually 1.0 to 20.0 liters, preferably 1.0 to 10.0 liters, based on mol.

The reaction temperature varies depending on the starting compound, reaction reagent, solvent and the like, but is usually from -20 ° C to 150 ° C, preferably from 10 to 100 ° C.

The reaction time varies depending on the starting compound, reaction reagent, solvent, reaction temperature and the like, but is usually 6 minutes to 48 hours, preferably 10 minutes to 24 hours.

In the step H, the substituent bonded to the oxygen atom of the hydroxyl group at the 4-position of the N-substituted dihydropyrrole derivative of the present invention represented by the general formula (II) is removed using a base in an inert solvent. And producing the compound of the present invention represented by the general formula (Ij). (Step H)

[0211]

Embedded image In the above formula, R ¹ , R ² , R ³ , A, X and n have the same meaning as described above, and R ¹⁰ is a C ₂ -C ₁₀ alkylcarbonyl group (the alkylcarbonyl group is the same or different 1 To 5
May be substituted by _one halogen atom or a C ₁ -C ₆ alkoxy group. ) Or a C ₂ -C ₈ alkoxycarbonyl group (the alkoxycarbonyl group is a halogen atom and a C
It may be substituted by the same or different 1 to 5 substituents selected from the group consisting of ₁ to ₆ alkoxy groups. (Preferably an acetyl group, a methoxycarbonyl group or an ethoxycarbonyl group).

The base to be used is not particularly limited as long as it usually has a pH of 8 or more. Examples thereof include hydroxides of alkali metals such as sodium hydroxide and potassium hydroxide; and hydroxides of calcium hydroxide and magnesium hydroxide. Alkaline earth metal hydroxides; alkali metal carbonates such as sodium carbonate and potassium carbonate; or alkali metal bicarbonates such as sodium hydrogen carbonate and potassium hydrogen carbonate. It is a hydroxide of an alkali metal, more preferably, sodium hydroxide or potassium hydroxide.

The amount of the base used is usually the same as that of the compound (I
I) It is 1.0 to 10.0 mol per 1 mol,
Preferably, it is 1.0 to 5.0 mol.

The solvent used is not particularly limited as long as it does not inhibit the reaction and dissolves the starting materials to some extent.
For example, alcohols such as methanol, ethanol, ethylene glycol and glycerin; ethers such as diethyl ether, dimethoxyethane, tetrahydrofuran and dioxane; ketones such as acetone, methyl ethyl ketone; esters such as ethyl acetate and ethyl propionate. And water; or a mixed solvent thereof, preferably water or alcohol, and more preferably water or methanol.

The amount of the solvent used depends on the amount of the compound (II)
It is usually 1.0 to 20.0 liters, preferably 1.0 to 10.0 liters, based on mol.

The reaction temperature varies depending on the starting compound, reaction reagent, solvent and the like, but is usually from -20 ° C to 150 ° C, preferably from 10 to 100 ° C.

The reaction time varies depending on the starting compound, reaction reagent, solvent, reaction temperature and the like, but is usually 6 minutes to 48 hours, preferably 10 minutes to 24 hours.

After completion of each of the above reaction steps, the target compound of each step can be collected from the reaction mixture according to a conventional method. For example, it can be obtained by appropriately neutralizing the reaction mixture, removing any insoluble matter by filtration, adding an organic solvent immiscible with water, washing with water, and distilling off the solvent. If necessary, the obtained target compound can be further purified by a conventional method, for example, recrystallization, reprecipitation or chromatography. In addition, the target compound of each step may be used in the next reaction step without generation. When a hydroxyl group is present in the compound, the compound can be synthesized by reacting a base in a solvent.

In the step I, the acetal moiety of the acetal derivative represented by the general formula (IIc) is converted to an oxime to give the compound (IId) which is an intermediate of the present invention.
This is the step of manufacturing. (Step I)

[0220]

Embedded image In the above formula, R ¹ , R ⁵ , A and n are as defined above,
^11, the C ₁ -C ₆ alkyl group (preferably, a C ₁ -C ₄ alkyl group, more preferably a C ₁ -C ₃ alkyl group, further preferably more, C ₁ -C _{2 is} an alkyl group.)
Is shown. (Step I-1) Step I-1 is to produce a ketone derivative represented by the general formula (IX) by reacting an acetal derivative represented by the general formula (IIc) with an acid in an inert solvent. This is the step of performing

The acid used in this step is not particularly restricted but includes, for example, mineral acids such as hydrochloric acid, sulfuric acid, perchloric acid and nitric acid; carboxylic acids such as formic acid, acetic acid and propionic acid; Sulfonic acids, which can be sulfonic acids such as benzenesulfonic acid, preferably mineral acids;
More preferably, it is hydrochloric acid or sulfuric acid.

The amount of the acid used is the same as in the compound (IIc) 1
Usually, it is 0.01 to 100 mol,
Preferably, it is 0.1 to 10 mol.

The solvent used in this step is not particularly limited as long as it does not inhibit the reaction and dissolves the starting materials to some extent. For example, water; alcohols such as methanol, ethanol and propanol; diethyl ether Ethers such as, dimethoxymethane, tetrahydrofuran and dioxane; nitriles such as aceto and nitrile;
Ketones such as acetone and methyl ethyl ketone; or a mixed solvent thereof, preferably water, alcohols or ketones, more preferably
Methanol, ethanol or acetone.

The amount of the solvent used is the same as that of compound (IX) 1
It is usually 1.0 to 20 liters, preferably 1.0 to 10.0 liters, based on mol.

The reaction temperature varies depending on the starting compound, reaction reagent, solvent and the like, but is usually from -10 ° C to 150 ° C, preferably from room temperature to 100 ° C.

The reaction time varies depending on the starting compound, the reaction reagent, the solvent and the reaction temperature, but is usually from 1 minute to 48 hours, preferably from 10 minutes to 24 hours. (Step I-2) Step I-2 is an intermediate of the present invention by reacting compound (IX) with an O-substituted hydroxylamine represented by the general formula (XIII) in an inert solvent. This is a step of producing a compound (IId).

The amount of compound (XIII) used in the present invention is usually 1.0 to 1.0 mol per mol of compound (IX).
10 mol, preferably 1.0 to 5.0 mol.

The solvent used in the present invention is not particularly limited as long as it does not inhibit the reaction and dissolves the starting materials to some extent. Examples thereof include water; alcohols such as methanol, ethanol and propanol; diethyl ether. Ethers such as, dimethoxymethane, tetrahydrofuran and dioxane; nitriles such as aceto and nitrile;
Carboxylic acids such as formic acid, acetic acid, and propionic acid; or a mixed solvent thereof, preferably water or alcohol, and more preferably water, methanol or ethanol.

The amount of the solvent used is the same as in the compound (IX) 1
It is usually 1.0 to 20 liters, preferably 1.0 to 10.0 liters, based on mol.

The reaction temperature varies depending on the starting compound, reaction reagent, solvent and the like, but is usually -10 ° C to 150 ° C.
Preferably it is room temperature to 100 ° C.

The reaction time varies depending on the starting compound, the reaction reagent, the solvent and the reaction temperature, but is usually from 1 minute to 48 hours, preferably from 10 minutes to 24 hours.

When the compound (I) of the present invention has a hydroxyl group, an alkali metal salt is prepared by using a base in an inert solvent.
It can be an alkaline earth metal salt or an ammonium salt.

The base used is, for example, an alkali metal hydroxide such as potassium hydroxide or sodium hydroxide; an alkali metal carbonate such as potassium carbonate or sodium bicarbonate; potassium bicarbonate or sodium bicarbonate. Alkali metal bicarbonates such as; calcium carbonate,
Alkaline earth metal carbonates such as magnesium carbonate;
Alkoxides such as sodium methoxide and sodium ethoxide; or amines such as ammonia, methylamine, ethylamine and triethylamine, preferably alkali metal hydroxides or amines, more preferably Is sodium hydroxide, potassium hydroxide or ammonia.

The solvent used is water; ethyl ether;
Ethers such as tetrahydrofuran; methanol,
Alcohols such as ethanol; esters such as ethyl acetate; aromatic hydrocarbons such as benzene and toluene; or aliphatic hydrocarbons such as hexane, preferably water or alcohols. And more preferably water, methanol or ethanol.

The amount of the solvent to be used is generally 1 to 20 liter, preferably 1 to 20 liter, per 1 mol of compound (I).
10 to 10 liters.

The reaction temperature is usually from -40 ° C to 150 ° C, preferably from 0 ° C to 100 ° C.

The reaction time is generally from 6 minutes to 48 hours, preferably from 10 minutes to 24 hours.

The compound (I) of the present invention is not an alkali metal salt, an alkaline earth metal salt or an ammonium salt as described above. When a basic moiety is present in the molecule, the compound (I) is prepared by using an acid in the presence of a solvent. Can be salted.

When the compound of the present invention is used as an active ingredient of a pesticide, the compound of the present invention may be used as it is, but it may be used as a carrier, a surfactant and other additives generally used for formulation as a pesticide adjuvant. Mixing auxiliary agents, for example, emulsions, suspensions, powders, granules, tablets, wettable powders, aqueous solvents, liquids, flowables, wettable powders, aerosols,
It can be formulated in various forms such as pastes, oils and emulsions. These compounding ratios are usually 0.1 to 9.0 parts by mass of the active ingredient and 10 to 99.9 parts by mass of the pesticide adjuvant.

Carriers used in the formulation include, for example, animal and plant powders such as starch, activated carbon, soybean powder, flour, wood powder, fish powder, milk powder, and talc, kaolin, bentonite, calcium carbonate, zeolite, diatomaceous earth, Solid carriers such as mineral powders such as white carbon, clay and alumina; or water, alcohols such as isopropyl alcohol and ethylene glycol, ketones such as cyclohexane and methyl ethyl ketone, ethers such as dioxane and tetrahydrofuran, kerosene and light oil. Such as aliphatic hydrocarbons, xylene, trimethylbenzene, tetramethylbenzenemethylnaphthalene, aromatic hydrocarbons such as solvent naphtha, halogenated hydrocarbons such as chlorobenzene, acid amides such as dimethylacetamide, and glycerin ester of fatty acid Esters etc., it can be a liquid carrier such as nitriles and dimethylsulfoxide sulfur-containing compounds such as de as acetonitrile, preferably a solid carrier or liquid carrier.

The surfactants used include, for example, metal salts of alkyl benzene sulfonic acid, metal salts of dinaphthyl methane disulfonic acid, alcohol sulfates, alkyl aryl sulfonates, lignin sulfonates, polyoxyethylene glycol ethers, and polyoxyethylene glycol ethers. It can be an ethylene alkyl aryl ether or a polyoxyethylene sorbitan monoalkylate, preferably a metal salt of an alkyl benzene sulfonic acid, a lignin sulfonate, a polyoxyethylene alkyl aryl ether or a polyoxyethylene sorbitan monoalkylate.

Other adjuvants include, for example, fixing agents or thickening agents such as carboxydimethylcellulose, gum arabic, sodium alginate, xanthan gum, guar gum, tragacanth gum and polyvinyl alcohol; antifoaming agents such as metal soaps; It may be a physical property enhancer coloring agent such as alkyl phosphate, silicone and paraffin, preferably guar gum or xanthan gum.

In the actual use, these preparations can be used as they are, or can be used after being diluted to a predetermined concentration with a diluent such as water. The application of various preparations containing the compound of the present invention or a diluent thereof is usually performed by a general application method, that is, spraying (eg, spraying, misting, atomizing, dusting, dusting, water surface application) , Box application, etc.), soil application (eg, mixing, irrigation, etc.), surface application (eg, application, dressing, coating, etc.), dipping or bait and the like. It is also possible to feed the livestock with the above-mentioned active ingredient by mixing it with the feed to control the generation and growth of harmful insects, especially harmful insects, in their excrement. It can also be applied by a so-called ultra-high concentration small amount spraying method. In this method, it is possible to contain 100% of the active ingredient.

The concentration of the active ingredient at the time of application of the pesticide of the present invention is usually 0.1 to 50,000 ppm, preferably 1 to 50,000 ppm.
10,000 ppm. However, the concentration of the active ingredient can be appropriately changed depending on the form of the preparation and the method, purpose, time, place and pest occurrence of the pest.For example, in the case of aquatic pests, the chemical solution of the above concentration is sprayed to the place of occurrence. Therefore, the concentration of the active ingredient in water is lower than the above. In the case of soil mixing treatment, the amount of the pesticide of the present invention is, for example, 0.1 to 5000 g, preferably 1 to 10 g, per 10 ares as an active ingredient compound.
00 g.

Needless to say, the compound of the present invention alone is sufficiently effective, but if necessary, fertilizers and other pesticides such as insecticides, acaricides, nematicides, fungicides, antibacterial agents, and the like. It can be mixed or used in combination with a virus agent, an attractant, a herbicide, a plant regulator, and the like, and in this case, a more excellent effect may be exhibited.

Other pesticides which can be used in combination with the compound of the present invention include, for example, insecticides, acaricides, nematicides, fungicides, antivirals, attractants, herbicides and plant regulators. Preferably, it is an insecticide, acaricide, nematicide, fungicide or herbicide.

The insecticides used can be, for example, organophosphorus and carbamate insecticides, pyrethroid insecticides or other insecticides.

The organic phosphorus and carbamate insecticides include, for example, fenthion, fenitrothion, diazinon, chlorpyrifos, oxydepphos, bamidione,
Fentoate, dimethoate, formothion, malathion, trichlorfon, thiomethone, phosmet, dichlorphos, acephate, EPBP, methyl parathion, oxydimetone methyl, ethion, dioxabenzophos, cyanophos, isoxathion, pyridafenthion, hosalone, methidathione, sulprophos, cloprophochlor. Tetrachlorvinphos, dimethylvinphos, propaphos, isofenphos, disulfoton, propenophos, pyraclofos, monocrotophos, azinphosmethyl, aldicarb, mesomil, thiodicarb, carbofuran, carbosulfan, benfracarb, fratiothiocarb, propoxur, fenobucarb, metrucarb, isoprocarb, carbaryl Pirimicarb, ethiophenecarb, Black fenthion, pirimiphos-methyl, quinalphos, chlorpyrifos-methyl, prothiofos, naled, EPN, XMC, bendiocarb, oxamyl, may be alanycarb or chlorobutyl phosphite.

The pyrethroid insecticides include, for example, permethrin, cypermethrin, deltamethrin, fenvalerate, fenpropatrin, pyrethrin, arethrin, tetramethrin, resmethrin, dimethrin, propasulin, phenothrin, prothrin, fluvalinate, cyfluthrin, cyhalothrin, flucitriline. Nate,
It can be etofenprox, cycloprothrin, tralomethrin, silafluofen, tefluthrin, bifenthrin or acrinatrine.

Other insecticides include, for example, diflubenzuron, chlorfluazuron, hexaflumuron, triflumuron, teflubenzuron, flufenoxuron, flucycloxuron, buprofezin, pyriproxyfen, lufenuron, cyromazine, methoprene, endosulfan, dia Fenthiuron, imidacloprid, fipronil, phenoxycarb, cartap, thiocyclam, bensultap, tebufenozide, chlorfenapyr, emamectin benzoate, acetamiprid, nitenpyram, pymetrozine, sodium oleate, nicotine sulfate, rotenone, metaldehyde, machine oil, T or oil It may be a microbial pesticide such as an entomopathogenic virus.

The acaricides to be used include, for example, chlorbenzylate, phenisobromolate, dicofol, amitraz, propargite, benzomate, hexthiazox, fenbutatin oxide, polynactin, quinomethionate, chlorfenson, tetradihon, abamectin , Milbemectin, Clofenthedine, Pyridabene, Fenpyroximate, Tebufenpyrad, Pyrimidifen, Fenothiocarb, Dienochlor, Ethoxazole, and Harfenprox.

The nematicide used can be, for example, fenamiphos, phosthiazate, etopropos, methyl isothiocyanate, 1,3-dichloropropene or DCIP.

The fungicides to be used include, for example, thiophanate methyl, benomyl, carbendazole, thiabendazole, forvet, thiuram, ziram, zineb, maneb, manzeb, polycarbamate, iprobenphos, edifenfos, fusaride, probenazole,
Isoprothiolane, chlorothalonil, captan, polyoxin, blasticidin S, kasugamycin, streptomycin, validamycin, tricyclazole,
Pyroquilon, phenazine oxide, mepronil, flutranyl, pencyclon, iprodione, hymexazole, metalaxyl, triflumizole, triforine, triadimefon, bitertanol, fenarimol, propiconazole, simoxanil, polochloraz, pefurazoate, hexaconazole, microbutane, diclometane, diclometane, diclometane , Dithianon, fosetyl, vinclozolin, procymidone, oxadixyl,
It can be guazatine, propamocarb hydrochloride, fluazinam, oxolinic acid, hydroxyisoxazole, imibenconazole or mepanipyrim.

The herbicides used include, for example, diflufenican, propanil, dichloropicolinic acid, dicamba,
Picoloram, 2,4-D, 2,4-DB, 2,4-D
P, fluroxypyr, MCPA, MCPP, triclopyr, diclohop-methyl, fenoxaprop-ethyl, fluazifop-butyl, haloxyfop-methyl, quizalofop-ethyl, norflurazon, chlorbropam, desmedifam, fenmedipham, profam, alachlor, acetochlor, Butachlor, metazachlor, metolachlor, pretilachlor, propachlor, oryzalin, trifluralin, acifluorfen, bifenox, fluorogligofen, fomesafen, halosaphen, lactofen, oxyfluorfen, chlortoluron, diuron, fluometuron, isoproturon, linuron, metabenzulone Alloxydim, Cretodim, Cycloxydim, Sethoxydim, Trakoxydim, Ima Tapil, imazamethabenz, imazapyr, imazaquin, bromoxynil, diclobenil, ioxinyl, mefenacet, amidosulfuron, bensulfuron-methyl, chlorimuron-ethyl, chlorsulfuron, sinosulfuron, metsulfuron-methyl, nicosulfuron, pyrimisulfuron, pyrazosulfuron-ethyl, Thifensulfuron-methyl,
Triasulfuron, tribenuron-methyl, butyrate, cycloate, gialate, EPTC, esprocalp, molinate, prosulfocalp, benthiocalp, trilate, atrazine, cyanazine, simazine, simetrine, terbutrin, terbutyrazine, hexazinone, metamitrone, metribuzine, amitriazole, amitriazole , Bentazone, cinmethirin, chromazone, clopyralid, difenzoquat, dithiopyr, ethofumesate, fluorochloridone, glufosinate, glyphosate, isoxaben, pyridate, quinclorac, quinmethac, sulfosate or tridiphane.

The compounds of the present invention include, for example, Hemiptera, Lepidoptera, Coleoptera, Diptera, Hymenoptera, Orthoptera, Termites, Thrips, Spider mites and plants It shows an excellent control effect on parasitic nematodes.
In addition, the compounds of the present invention exhibit excellent control effects on other pests, unpleasant animals, sanitary pests and parasites.

As the pests of the order Hemiptera, for example, Riptortus clavatus, southern stink bug (Nezara viridula),
Red stink bugs (Lygus sp.)
us), Nashigumbai (Stephanitis na)
shi) and other stink bugs (Heteroptera; Heteropte)
ra), leafhopper (Nephotettix)
cincticeps), leafhopper (Empoas)
ca sp. , Erythroneura sp. ,
Circulifer sp. ), Leafhoppers such as brown leafhoppers (Nilaparbatalugen)
s), staghorn planthopper (Sogatalla furci)
fera), Japanese brown planthopper (Laodelfax)
grasshoppers such as striatellas), Psylla
sp. Lice such as white lice, whitefly (Bemi)
sia tabaci), Whitefly on whitefly (Tri)
whiteflies, such as aleurodes vaporariorum, and grape aphids (Viteusv)
itifolii), peach aphid (Myzus)
persicae) and apple aphids (Aphis)
pomi), Cotton Aphid (Aphisgossy)
pii), Aphis fabae, Aphids aphid (Liphis erysimi), Potato beetle aphid (Aulacorthum sol)
ani), wheat midge aphid (Schizaphi)
aphids such as sgraminum) and Pseudococcus comstoc
ki), Ruby beetle (Ceroplastesru)
bens), San Jose scale insects (Comstoc)
caespis perniciosa, Unapsis yanoensis and other scales such as scale insects and turtles (Rhodnius sp.).
Is mentioned.

As the lepidopteran pests, for example, Chamonaki (Homona magnanima), Kokemon monakiki (Adoxophys orana), and Staghamaki (Sparganothis pillarian)
a), Nasihime Shingui (Grapholitham)
olesta), Mameshin iga (Leguminiv)
ora glycinivorella), codling moth (Laspeyresia pomonella), E
ucosma sp. , Lobesia botran
a, etc., and Grape Hosohamaki (Eupoeci)
llia ambiguella), Bombalina sp. , Moths (Nemapogon granellus), squirrels (Tineapellionella), etc., ginseng molymoga (Lyonetiapruni)
folliella, etc., and the typhoon moth moth (Phylnolyctor ringoniel)
la) etc .;
Scutellaria moth, such as Cnistis citellella, and Plutella xylostell
a), Suga such as Plays citri, grape sashiba (Nokona vegale), Synanth
edon sp. Scabby, cotton red bug (P
ectinophora gossypiella),
Potato moth (Phthorimaeapercul)
ella), Stopteryx sp. Mosquitoes, peach sink moth (Carposina nipo)
nensis), Iruga (Monem)
a flavescens, etc., Japanese squid (Chilo suppressalis), and the Japanese frog (Cnaphalocrocis median)
is), Ostrinia nubilalis, Awanomeiga (Ostrinia furnacali)
s), Himuradanomeiga (Hellula unda)
lis) Honey (Galleria mellon)
ella), Elasmopalpus lignos
ellus, Loxostege scientific
moss such as is, cabbage butterfly (Pieris r)
apae) and white butterflies, Artemisia japonicus (As
pterodactyls such as Cotisselenaria, Kalehaga such as Malcosomaneustria, sparrows such as Manduca sexta, and Eupoctis pseudodoc.
onspersa), Gypsy moth (Lymantria)
dispar, etc., Hokutriga, such as Hyphantria cunea, and tobacco badworm (Heliothis vir)
escens), ball worm (Helikoverp)
a zea), Spodoptera litura (Spodopte)
ra exigua) and Helicov (Helicov)
erpa armigera), Spodoptera litura (Sp)
podoptera litura) and the armyworm (Mam)
estra brassicae), Tamanayaga (Ag)
rotis ipsilon), armyworm (Pseu)
and noctuids such as daleia separata and Trichoplusia ni.

Examples of the insects of the order Coleoptera include, for example, Anemona cuprea, Bean beetle (Popillia japonica), Anadara rufocuprea, and Euth.
beetles such as eolalugiceps, wire worms (Agricotes sp.), Conode
us sp. Beetles such as the beetle, and the Japanese lady beetle (Epilachna vicientoctop)
uncata), Ladybug (Epila)
ladybirds such as chna varivestis, and Tribolium cast
anemone), beetles such as beetles, Anoplophora malasiaca, and Monochamus alte
beetles such as C. rnatas, bean weevil (Acanthoscelides obect)
us), adzuki beetle (Callosobruchu)
bean weevil, such as S. chinensis, and Colorado potato beetle (Leptinotarsa decemli)
neata), corn rootworm (Diabroti)
ca sp. ), Olema o
ryzae), Tency beetle (Chaetocn)
ema concinna), Phaedon coc
hlearias, Olema melanopu
s, leaf beetles such as Diclatispa armigera, weevil weevil such as Apion godmani, rice weevil (Lissorhoptrus)
oryzophilus, cotton weevil (Ant)
weevil such as Homomus grandis, and weevil (Sitophilus Zeamais)
And weevil, bark beetle, beetle beetle, and beetle.

Examples of the dipteran insect pests include, for example, the giant crab (Tipula aino) and the rice midge (Ch).
(ironomus oryzae), rice scintillation fly (Orseolia oryzae), medfly (Ceratitis capitata),
Rice Flies (Hydrellia griseol)
a), Drosophila (Drosophil)
a suzukii), Fritz fries (Oscine)
lla frit), rice flies (Chlorops)
oryzae), haricot fly (Ophiom)
yia phaseoli)
riomyza trifolii, Pegomya hyoscyami, Tanfly (Delia platura), Sorghum fry (Atherigona soccata), Musca domestica (Musca domesica)
trophilus sp. ), Fly (Stom)
oxys sp. ), Aedes aegypti (Aedes a)
egypti), Culex pipiens
ns), Anopheles sln
ensis) and Culex pipiens (Culex tr)
itaeniorhynchus).

Examples of hymenoptera pests include, for example, wasps (Cephus sp.) And honey bees (Harm).
olita sp. ), Alaska bee (Athalia)
rosae), hornet (Vespa manda)
rina) and fire ant.

As pests of the order Orthoptera, for example, German cockroaches (Blattella germanica) and cockroaches (Periplaneta americic)
ana), Kera (Grylotalpa afric)
ana), grasshopper (Locusta migrator)
ia migratriodes) and Melano
plus sanguinipes.

As a thrips pest, for example, Thrips thrips dor
salis) and Thrips palmi (Thrips)
palmi), Croton thrips (Helioth)
rips haemorrhoidalis, Citrus thrips (Frankliniella oc)
C. centralis) and Thrips palmi (Ha)
plothripsaculeatus).

As the spider mites, for example, spider mites (T
etranychus urticae), Kanzawa spider mite (Tetranychus kanzawa),
Citrus red mite (Panonychus citri),
Apple spider mite (Panonychus ulmi), yellow mites (Eotetranychus carp)
ini), Texas Citrus Mite (Eotetran)
ychus banksi), citrus red mite (Acu)
lops pelekassi, Polyphagotarsonemus latu
s);
p. ), Robin mite (Rhizoglyphus r)
obini) and Tyrophagu
s putresentiae).

As the plant parasitic nematodes, for example, sweet potato nematodes (Meloidogyne in
cognita), Negusaresenchu (Pratyl)
enchus sp. ) Soy cyst nematode (He
terodera glycines), rice squirrel nematode (Apelenchoides bess)
eyi) and pine wood nematode (Bursaphe)
Lenchus lignicolus).

As other pests, unpleasant animals, sanitary pests and parasites, for example, scrimming mussels (Pomac
ea canaliculata, slugs (Inc.)
ilaria sp. ), African Maimai (Acha
Gastropods (Gastro) such as tina fulica
poda), dung beetle (Armadillidium)
sp. ), Isopoda, Isopoda, Centipede, etc. (Iso
poda), Liposcelis sp. Etc., Ctenolepisma sp. Stains such as Pulex sp. , Ctenocephalid
es sp. Fleas, etc., Trichodicts
sp. Lice such as Cimex sp. Bed lice such as bed bugs and ox tick (Boophilus micr)
opulus), Haemaphys
aris longicornis) and Dermatophagoides pteronyssinus.

Further, the compounds of the present invention are also effective against pests which are resistant to organophosphorus compounds, carbamate compounds, synthetic pyrethroid compounds, acylurea compounds or existing insecticides.

The compounds of the present invention can be used as defoliants, plant growth regulators or herbicides. The compounds of the present invention act as non-selective or selective herbicides on crops, depending essentially on the amount used.

The compounds of the present invention can be used, for example, for the following weeds in the following cultivated plant situations, but the present invention is not limited to these.

As dicotyledon cultivation plants, for example, cotton genus (Gossypium), soybean genus (Glycin)
e), Chard genus (Beta), carrot genus (Dau)
cus), common bean (Phaseolus), pea (Pisum), eggplant (Solanum),
Flax (Linum), Sweet Potato (Ipomoe)
a), Vicia, Nicotiana
tiana), tomato (Lycopersico)
n), Peanuts (Arachis), Brassica (Brassica), Lactucus (Lactuc)
a) Cucumber and Cucumber (Cu)
curbita).

As dicotyledon weeds, for example, mustard (S
inapis), genus Lepidid
ium), the genus Glium, the genus Hakobe (S
telaria), daisies (Mairikari)
a), genus Anthemis, Galinsoga, Chenos (Cheno)
podium), nettle genus (Urtica), kion genus (Snecio), Amaranthus (Amaranthu)
s), Portulaca, Xanthium, Convolv
ulus), Ipomoea, Polygonum, Sesbania (Sesban)
ia), ragweed (Ambrosia), thistle (Cirsium), genus Circum (Carduu)
s), genus Sonchus, genus eggplant (Sola)
num), the genus Rorippa, the genus Rotalia, the genus Azena (Linderni)
a), the genus Lamium, the genus Veronica, the genus Abutilo
n), genus Emex, genus Datura (Dataura), violet genus (Viora), genus Galeopsis, Poppy genus (Papav)
er), the genus Centaurea, the genus Trifolium, and the genus Rosa (R)
anunculus and dandelion (Taraxac)
um).

As monocotyledon cultivation plants, for example, rice genus (Oryza), corn genus (Zea), wheat (Triticum), barley (Hordeu)
m), oat (Avena), rye (Se
calli), sorghum (Sorghum), millet (Panicum), sugarcane (Saccharu)
m), the genus Ananas, the genus Asparagus, and the genus Allium.

As monocotyledonous weeds, for example,
hinochloa), Enokorogosa (Setari)
a), millet genus (Panicum), crabgrass genus (Dig)
italia, genus Phleum, genus Poa (Poa), genus Bosch (Fest)
uca), Eleusine, Brachiaria, Lolium (Lol)
ium), genus (Bromus), genus (Avena), genus Cyper (Cyper)
us), Sorghum, Agropyron, Cynodon (Cynodo)
n), the genus Monochoria, the genus Fembristis, the genus Omodaka (Sa)
gittaria), the genus Eleochari (Eleochari)
s), genus Scirpus, genus Paspalum, genus platypus (Ischaem)
um), the genus Dactylocteni
um), the genus Agrosis, the genus Alopecurus and the genus Apera
a).

The compounds according to the invention are suitable, depending on the concentration, for example for the control of weeds on industrial lands, railway premises, roads and squares with and without trees. Similarly, the compound of the present invention can be used for cultivating plants such as perennial cultivated plants, for example, afforestation, ornamental trees, orchards, vineyards, citrus grove, walnut orchards, tea gardens, cacao plantations, planting small fruit trees and hops. It can be used for weed control inside,
It can also be used for the selective control of weeds in annual plants. The compound of the present invention is extremely excellent in selective control of monocotyledon weeds before and after germination in dicotyledonous plants.

BEST MODE FOR CARRYING OUT THE INVENTION The compound of the present invention will be specifically described below with reference to Examples, Preparation Examples and Test Examples, but the present invention is not limited to these. .

[0275]

【Example】

[0276]

Example 1 5,5-Dimethyl-4-hydroxy-1-
Methoxy-2-oxo-3- (2,4,6-trimethylphenyl) -2,5-dihydro-1H-pyrrole (Compound No. 1-13) (1) 2- [N-methoxy-N-[(2 , 4,6-Trimethylphenyl) acetyl] amino-2-methylpropionic acid ethyl ester (Compound No. 8-
33, Step A-1) Chloride (2,4,6-trimethylphenyl) acetic acid (10
1.2 mg), triethylamine (0.15 ml) and dimethylaminopyridine (5 mg) were dissolved in dichloromethane (5 ml), and 2-methoxyamino-2-methylpropionic acid ethyl ester (0.25 ml) was dissolved.
g) was added at 0 ° C., and the mixture was stirred at the same temperature for 1 hour. After completion of the reaction, dichloromethane was added, the dichloromethane layer was separated, washed with water, and dried over magnesium sulfate. The solvent was distilled off, and the obtained residue was subjected to silica gel column chromatography (elution solvent: ethyl acetate / hexane = 1/1).
0) to give the title compound (131.1 mg, yield 4).
1.0%). ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.84 (2H, s), 4.19 (2H, q, J
= 7.0), 3.93 (3H, s), 3.54 (2H, s), 2.24 (3H, s),
2.22 (6H, s), 1.54 (6H, m), 1.19 (3H, t, J = 7.0). Physical properties: oil. (2) 5,5-dimethyl-4-hydroxy-1-methoxy-2-oxo-3- (2,4,6-trimethylphenyl) -2,5-dihydro-1H-pyrrole (Compound No. 1-13, Step A-2) 2- [N-methoxy-N-[(2,
4,6-trimethylphenyl) acetyl] amino-2-
Methyl propionic acid ethyl ester (13
1.1 mg) of dimethylformamide solution (3 ml)
To the mixture was added potassium t-butoxide (65.0 mg), and the mixture was stirred at room temperature for 30 minutes. After completion of the reaction, the reaction solution was poured into water, the aqueous layer was separated, and washed with diethyl ether. The aqueous layer was neutralized with 1N hydrochloric acid, extracted with ethyl acetate, washed with saturated saline, and dried over magnesium sulfate. The solvent is distilled off, and the obtained residue is subjected to thin-layer chromatography (developing solvent: ethyl acetate / hexane = 1/1).
And purified the title compound (35.4 mg, yield 31.7).
%). ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.92 (2H, s), 5.86 (1H, brd.
s), 3.96 (3H, s), 2.28 (3H, s), 2.15 (6H, s), 1.52
(6H, s). Physical properties: crystals (melting point: 204-207 ° C).

[0277]

Example 2 2- [N-hydroxy-N-[(2-chlorophenyl) acetyl] amino-2-methylpropionic acid ethyl ester (Compound No. 8-17)
1. Step A-1) (2-chlorophenyl) acetic acid (0.34 g), 2-methoxyamino-2-methylpropionic acid methyl ester (0.36 g) and 2-chloro-1 iodide
To a dichloromethane solution (8 ml) of -methylpyridinium (0.76 g) was added triethylamine (0.42 ml) at 0 ° C, and the mixture was stirred at room temperature for 2 hours, and further refluxed for 3 hours. After completion of the reaction, dichloromethane was added, and the dichloromethane layer was washed with water and dried over magnesium sulfate.
The solvent was distilled off, and the obtained residue was subjected to silica gel column chromatography (elution solvent: ethyl acetate / hexane = 1 /
Purification by 10) afforded the title compound (477.0 mg, yield 76.0%). ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.39-7.18 (4H, m), 4.15 (2H,
q, J = 7.0), 4.00-3.85 (2H, m), 3.91 (3H, s), 1.66-
1.46 (6H, m), 1.23 (3H, t, J = 7.0). Physical properties: oil.

[0278]

Example 3 5,5-Dimethyl-4-hydroxy-1-
Methoxymethoxy-2-oxo-3- (2,4,6-trimethylphenyl) -2,5-dihydro-1H-pyrrole (Compound No. 1-99) (1) 2- [N-hydroxy-N-[( 2,4,6-
Trimethylphenyl) acetyl] amino-2-methylpropionic acid ethyl ester (Compound No. 8)
-13, Step B-1) (2,4,6-trimethylphenyl) acetic acid (7.84)
g) and thionyl chloride (3.37 ml) in toluene (80 ml) were added to a catalytic amount of dimethylformamide (2 ml).
) And heated to reflux for 1 hour. After concentrating the solvent, the obtained mixture was dissolved in ethyl acetate (40 ml), and the solution was added to 2-methoxyamino-2-methylpropionic acid ethyl ester (5.90 g) and sodium bicarbonate (3.70 g). ) Was added to ethyl acetate (60 m
1) It was added dropwise to a mixed solvent of -water (40 ml) at 20 ° C.
After completion of the dropwise addition, the mixture was stirred at 0 ° C. for 1 hour. After completion of the reaction, the reaction solution was distributed, and the organic layer was washed with saturated saline and dried over sodium sulfate. The solvent was distilled off, and the obtained residue was purified by silica gel column chromatography (elution solvent: ethyl acetate / hexane = 1/4) to give the title compound (5.46, 44.3% yield) and 2%. − [(2,4,6-
Trimethylphenyl) acetoxy] amino-2-methylpropionic acid ethyl ester (2.09
g, yield 17.0%).

2- [N-hydroxy-N-[(2,4,
6-Trimethylphenyl) acetyl] amino-2-methylpropionic acid ethyl ester: ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.68 (1H, s), 6.84 (2H,
s), 4.01 (2H, q, J = 7.1), 3.64 (2H, s), 2.28 (6
H, s), 2.25 (3H, s), 1.32 (6H, s), 1.16 (3H, t, J =
7.1). Physical properties: oil.

2-[(2,4,6-trimethylphenyl)
A) Acetoxy] amino-2-methylpropionic acid
Cid = ethyl ester:¹ H-NMR (CDCl_Three) δ (ppm): 7.68 (1H, s), 6.84 (2H, s),
4.01 (2H, q, J = 7.1), 3.64 (2H, s), 2.28 (6H, s),
2.25 (3H, s), 1.32 (6H, s), 1.16 (3H, t, J = 7.1). Physical properties: oil. (2) 2- [N-methoxymethoxy-N-[(2,
4,6-trimethylphenyl) acetyl] amino-2-
Methyl propionic acid = ethyl ester (compound
Product No. 8-48, Step B-2) 2- [N-hydroxy-N- obtained by (1)
[(2,4,6-trimethylphenyl) acetyl] amido
No-2-methylpropionic acid ethyl ester
(Compound No. 8-13) (1.01 g) in dimethyl
Sodium hydride in formamide solution (10 ml)
(0.15 g in 60% mineral oil) at 0 ° C.
And stirred for 10 minutes. Add chlorodimethyl ether to the reaction solution.
(0.30 ml) was added at 0 ° C. 1 hour at the same temperature
While stirring at room temperature for 2 hours.
Ether (0.1 ml) and sodium hydride (60%
0.05 g in mineral oil) was added at 0 ° C. 1 hour at the same temperature
During the stirring, the mixture was stirred at room temperature for 2 hours and further at 40 ° C. for 2 hours. Anti
After the reaction, pour the reaction solution into water and extract with ethyl acetate.
Was. Wash with saturated saline and dry with magnesium sulfate
did. The solvent is distilled off, and the obtained residue is
Chromatography (elution solvent: ethyl acetate / hexane
= 1/20) to give the title compound (1.12 g, yield
97.0%). ¹ H-NMR (CDCl_Three) δ (ppm): 6.84 (2H, s), 5.94 (2H, s),
4.09 (2H, q, J = 7.3), 3.90 (2H, s), 3.63 (3H, s),
2.24 (3H, s), 2.21 (6H, s), 1.52 (6H, brd.s), 1.18
(3H, t, J = 7.3). Physical properties: oil. (3) 5,5-dimethyl-4-hydroxy-1-methoate
Xymethoxy-2-oxo-3- (2,4,6-trime
Tylphenyl) -2,5-dihydro-1H-pyrrole
(Compound No. 1-99, Step A-2) 2- [N-methoxymethoxy-N obtained by (2)
-[(2,4,6-trimethylphenyl) acetyl] a
Mino-2-methylpropionic acid-ethyles
Ter (Compound No. 8-48) (351.2 mg)
Potassium t-butyl was added to the tilformamide solution (7 ml).
Toxide (123.8 mg) was added and stirred at room temperature for 3 hours.
Stirred. Pour the reaction solution into water, separate the aqueous layer,
Washed with ether. Neutralize the aqueous layer with 1N hydrochloric acid and add vinegar.
After extraction with ethyl acetate and washing with saturated saline,
It was dried with gnesium. The solvent is distilled off and the residue obtained
To silica gel column chromatography (elution solvent: vinegar)
(Ethyl acetate / hexane = 1/3) to give the title compound
(227.1 mg, yield 73.4%).¹ H-NMR (CDCl_Three) δ (ppm): 6.91 (2H, s), 6.48 (1H, brd.
s), 5.01 (2H, s), 3.59 (3H, s), 2.28 (3H, s), 2.14
(6H, s), 1.51 (6H, s). Physical properties: Crystal (melting point: 151-153 ° C).

[0281]

EXAMPLE 4 2,2-Dimethylpropionic acid = 5,5-dimethyl-1-methoxy-2-oxo-3-
(2,4,6-trimethylphenyl) -2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 1-19, Step A-3) 5,5-dimethyl obtained according to Example 1 -4-Hydroxy-1-methoxy-2-oxo-3- (2,4,6-
To a solution of trimethylphenyl) -2,5-dihydro-1H-pyrrole (Compound No. 1-13) (412.1 mg) and triethylamine (0.25 ml) in dichloromethane (5 ml) was added pivaloyl chloride (0.22 ml) in 0 ml.
Added at ° C. The mixture was stirred at the same temperature for 1 hour and subsequently at room temperature for 2 hours. After completion of the reaction, dichloromethane was added, the dichloromethane layer was separated, washed with water, and dried over magnesium sulfate. The solvent was distilled off, and the obtained residue was subjected to silica gel column chromatography (elution solvent: ethyl acetate /
Hexane = 1/10) to give the title compound (46
8.2 mg, yield 86.8%). ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.82 (2H, s), 4.00 (3H, s),
2.24 (3H, s), 2.16 (6H, s), 1.48 (6H, s), 1.07 (9
H, s). Physical properties: Crystal (melting point: 101-103 ° C).

[0282]

EXAMPLE 5 Dithiocarbonate = S-ethyl = ester = O-
[5,5-dimethyl-1-methoxy-2-oxo-3-
(2,4,6-trimethylphenyl) -2,5-dihydro-1H-pyrrol-4-yl] ester (Compound No. 1-51, Step A-3) Thiophosgene was added to tetrahydrofuran (5.0 ml) at 0 ° C. (1.4 ml), ethyl mercaptan (1.3 m
l) and pyridine (1.5 ml) were added, and the mixture was stirred at room temperature for 50 minutes. The reaction solution was cooled to 0 ° C., triethylamine (2.5 ml) and 5,5-dimethyl-4-hydroxy-1-methoxy-2-oxo-3 obtained according to Example 1.
-(2,4,6-trimethylphenyl) -2,5-dihydro-1H-pyrrole (Compound No. 1-13) (1.6
A solution of 4 g) in tetrahydrofuran (9.0 ml) was added, and the mixture was stirred at room temperature for 3 hours. The reaction solution was poured into water, extracted with ethyl acetate, and the extract was dried over anhydrous magnesium sulfate. The solvent was distilled off, and the obtained residue was subjected to silica gel column chromatography (elution solvent: ethyl acetate / hexane =
1/7) to give the title compound (1.60 g, yield 7).
0.5%). ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.80 (2H, s), 4.00 (3H, s),
2.98 (2H, q, J = 7.3), 2.23 (3H, s), 2.17 (6H, s),
1.56 (6H, s), 1.17 (3H, t, J = 7.3). Physical properties: oil.

[0283]

EXAMPLE 6 Carbonic acid = 2,2-dimethylpropyl ester = 5,5-dimethyl-1-methoxy-2-oxo-3
-(2,4,6-trimethylphenyl) -2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 1-38, Step A-3) 2,2-dimethylpropyl alcohol (156.6 m)
g) in dichloromethane solution (1 ml) was added triphosgene (129.3 mg) and pyridine (0.12 ml) at 0 ° C.
And stirred at the same temperature for 60 minutes. The reaction solution was treated with 5,5-dimethyl-4-hydroxy-1-methoxy-2-oxo-3- (2,4,6-trimethylphenyl) -2,5-dihydro-1H- obtained in Example 1. Pyrrole (Compound No. 1-13) (200 mg) and triethylamine (0.20 ml) in dichloromethane (2 ml)
At 0 ° C. and stirred at the same temperature for 1 hour. After the reaction,
The reaction solution was poured into water and extracted with ethyl acetate. The organic layer was washed with brine and dried over magnesium sulfate. The solvent was distilled off, and the obtained residue was subjected to silica gel column chromatography (elution solvent: ethyl acetate / hexane =
1/10) to give the title compound (173.5 mg,
Yield 63.3%). ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.84 (2H, s), 4.01 (3H, s),
3.67 (2H, s), 2.21 (3H, s), 2.17 (6H, s), 1.54 (6
H, s), 0.78 (9H, s). Physical properties: oil.

[0284]

Example 7 5,5-Dimethyl-1-methoxy-4-methoxymethoxy-2-oxo-3- (2,4,6-trimethylphenyl) -2,5-dihydro-1H-pyrrole (Compound No. 1) -59, Step A-3) A mixture of sodium hydride (12.9 mg in 60% mineral oil) and dimethylformamide (0.5 ml) was added at 0 ° C.
5,5-dimethyl-4-hydroxy-1-methoxy-2-oxo-3- (2,4,6) obtained by Production Example 1
A solution of (trimethylphenyl) -2,5-dihydro-1H-pyrrole (Compound No. 1-13) (27.9 mg) in dimethylformamide (1.0 ml) and chlorodimethylether (20 μl) were added, and the mixture was stirred at room temperature for 30 minutes. . The reaction solution was poured into water and extracted with ethyl acetate. The organic layer was washed with brine and dried over magnesium sulfate. The solvent was distilled off, and the obtained residue was purified by thin-layer chromatography (developing solvent: ethyl acetate / hexane = 1/3) to give the title compound (25.4 mg, yield 79.5%).
I got ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.85 (2H, s), 4.69 (2H, s),
3.96 (3H, s), 3.37 (3H, s), 2.26 (3H, s), 2.14 (6
H, s), 1.51 (6H, s). Physical properties: oil.

[0285]

Example 8 5,5-Dimethyl-4-hydroxy-1-
Methoxymethoxy-2-oxo-3- (2,4,6-trimethylphenyl) -2,5-dihydro-1H-pyrrole (Compound No. 1-99, Steps B-2 and A-2) Example 3 (1 2-)-N-hydroxy-
N-[(2,4,6-trimethylphenyl) acetyl]
Amino-2-methylpropionic acid ethyl ester (Compound No. 8-13) (8.10 g) and chlorodimethylether (1.72 ml) in dimethylformamide solution (80 ml) were mixed with sodium hydride (60%
1.1 g) in mineral oil was added at 0 ° C. After stirring at the same temperature for 2 hours, sodium hydride (60% in mineral oil,
0.40 g), and the mixture was stirred at 0 ° C. for 1 hour and at room temperature for 2 hours. The reaction solution was added to dimethylformamide (80 m
l) and potassium t-butoxide (3.60 g)
At the same temperature for 1 hour, at room temperature for 1 hour, and further at 40 ° C.
For 2 hours. The reaction solution was poured into water, the aqueous layer was separated, and washed with diethyl ether. The aqueous layer was neutralized with 1N hydrochloric acid, extracted with ethyl acetate, washed with brine, and dried over magnesium sulfate. Evaporate the solvent,
The obtained residue was purified by silica gel column chromatography (elution solvent: ethyl acetate / hexane = 1/1) to give the title compound (6.44 g, yield 88.8%). ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.91 (2H, s), 6.48 (1H, brd.
s), 5.01 (2H, s), 3.59 (3H, s), 2.28 (3H, s), 2.14
(6H, s), 1.51 (6H, s). Physical properties: Crystal (melting point: 151-153 ° C).

[0286]

Example 9 2- [N-hydroxy-N-[(2,4,
6-trimethylphenyl) acetyl] amino-2-methylpropionic acid methyl ester (Compound No. 8-3) (1) N- (α-cyano-α, α-dimethylmethyl)
-N-hydroxy-2- (2,4,6-trimethylphenyl) acetamide (Compound No. 9-1, Step C-1) (2,4,6-trimethylphenyl) acetic acid (5.36)
g) and thionyl chloride (1.75 ml) in toluene (36 ml) were added to a catalytic amount of dimethylformamide (1
) And heated to reflux for 1 hour. After evaporating the solvent, the residue was dissolved in ethyl acetate (25 ml), and the solution was added to 2-hydroxyamino-2-methylpropionitrile (2.20).
g) and a mixed solvent of ethyl acetate (40 ml) and water (20 ml) in which sodium bicarbonate (2.52 g) was dissolved,
It was added dropwise at 0 ° C. After completion of the dropwise addition, the mixture was stirred at the same temperature for 2 hours. After completion of the reaction, the reaction solution was distributed, and the organic layer was washed with saturated saline and dried over sodium sulfate. The solvent was distilled off, and the obtained residue was purified by silica gel column chromatography (eluent: ethyl acetate / hexane = 1/4) to give the title compound (4.09 g, yield 78.5%).
And 2-[(2,4,6-trimethylphenyl) acetoxy] amino-2-methylpropionitrile (1.10.
g, yield 21.1%).

N- (α-cyano-α, α-dimethylmethyl) -N-hydroxy-2- (2,4,6-trimethylphenyl) acetamide: ¹ H-NMR (DMSO-d ₆ ) δ (ppm) : 10.36 (1H, s), 6.82 (2H,
s), 3.74 (2H, s), 2.20 (3H, s), 2.13 (6H, s), 1.63
(6H, s). Physical properties: amorphous.

2-[(2,4,6-trimethylphenyl) acetoxy] amino-2-methylpropionitrile: ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.61 (1H, s), 6.88 (2H , s),
3.79 (2H, s), .32 (6H, s), 2.26 (3H, s), 1.51 (6H,
s). Physical properties: oil. (2) 2- [N-hydroxy-N-[(2,4,6-
Trimethylphenyl) acetyl] amino-2-methylpropionic acid methyl ester (Compound No. 8
-3, Step C-2) Concentrated sulfuric acid (0.7 ml) was added to the N-
A chloroform solution (5 ml) of (α-cyano-α, α-dimethylmethyl) -N-hydroxy-2- (2,4,6-trimethylphenyl) acetamide (Compound No. 9-1, 0.30 g) was added at 0 ° C. And stirred at 0 ° C. for 30 minutes and at 40 ° C. for 1.5 hours. The reaction solution was cooled again to 0 ° C, methanol (0.5 ml) was added, and the mixture was stirred at 0 ° C for 1 hour at 40 ° C.
For 1.5 hours. After the completion of the reaction, the reaction solution was poured into ice and extracted with ethyl acetate. The organic layer was washed with a saturated saline solution and dried over magnesium sulfate. The solvent was distilled off, and the obtained residue was purified by silica gel column chromatography (elution solvent: ethyl acetate / hexane = 1/4) to obtain the title compound (56.6 mg, yield 16.8%). Was. ¹ H-NMR (DMSO-d ₆ ) δ (ppm): 10.03 (1H, s), 6.78 (2H,
s), 3.67 (2H, s), 3.51 (3H, s), 2.19 (3H, s), 2.10
(6H, s) 1.36 (6H, s). Physical properties: oil.

[0289]

Example 10 2,2-Dimethylpropionic acid = 5,5-dimethyl-1-chloromethoxy-2-oxo-3- (2,4,6-trimethylphenyl) -2,5
-Dihydro-1H-pyrrol-4-yl = ester (Compound No. 1-176) (1) 2,2-dimethylpropionic acid =
5,5-dimethyl-1-hydroxy-2-oxo-3-
(2,4,6-trimethylphenyl) -2,5-dihydro-1H-pyrrol-4-yl = ester (Compound No. 1-6, D-1) 2,2-dimethyl produced according to Example 4 Propionic acid = 5,5-dimethyl-1-methoxymethoxy-2-oxo-3- (2,4,6-trimethylphenyl) -2,5-dihydro-1H-pyrrol-4-yl =
To a dichloromethane solution (10 ml) of the ester (Compound No. 1-105) (0.78 g), trimethylsilane bromide (2.6 ml) and Molecular Sieve 3A were added at 0 ° C, and the mixture was stirred at room temperature for 3.5 hours. After completion of the reaction, the reaction solution was poured into aqueous sodium hydrogen carbonate, extracted with ethyl acetate, washed with saturated saline, and dried over magnesium sulfate. The solvent was distilled off, and the obtained residue was purified by silica gel column chromatography (elution solvent: ethyl acetate / hexane = 1/3) to obtain the title compound (0.55 g, yield 79.6%). Was. ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.82 (2H, s), 2.24 (3H, s),
2.13 (6H, s), 1.45 (6H, s), 1.07 (9H, s). Physical properties: crystals (melting point: 198-199 ° C). (2) 2,2-dimethylpropionic acid =
5,5-dimethyl-1-chloromethoxy-2-oxo-
3- (2,4,6-trimethylphenyl) -2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 1-176, Step D-2) 2,2 obtained by (1) -Dimethylpropionic acid = 5,5-dimethyl-1-hydroxy-2-oxo-3- (2,4,6-trimethylphenyl) -2,
To a solution of 5-dihydro-1H-pyrrol-4-yl ester (Compound No. 1-6) (200.0 mg) in dimethylformamide (2 ml) was added sodium hydride (60 ml).
% Mineral oil, 27.8 mg) and chloroiodomethane (50%).
μl) at 0 ° C. The mixture was stirred at the same temperature for 30 minutes and further at room temperature for 2 hours. The reaction solution was poured into water, extracted with ethyl acetate, washed with saturated saline, and dried over sodium sulfate. The solvent was distilled off, and the obtained residue was purified by silica gel column chromatography (elution solvent: ethyl acetate / hexane = 1/3) to give the title compound (137.4).
g, yield 60.1%). ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.84 (2H, s), 5.86 (2H, s),
2.26 (3H, s), 2.16 (6H, s), 1.51 (6H, s), 1.08 (9
H, s). Physical properties: Crystal (melting point: 124-126 ° C).

[0290]

Example 11 2,2-Dimethylpropionic acid = 5,5-dimethyl-1- (2,2,2-trifluoroethoxymethoxy) -2-oxo-3- (2,4,6
-Trimethylphenyl) -2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 1-180,
Step G) 2,2,2-trifluoroethanol (16.6 μl)
In dimethylformamide solution (1 ml) and sodium hydride (11.0 mg in 60% mineral oil)
2,5-dimethylpropionic acid obtained by the following method: 5,5-dimethyl-1-chloromethoxy-2-oxo-3- (2,4,6-trimethylphenyl) -2,5
-Dihydro-1H-pyrrol-4-yl ester (Compound No. 1-176) (90.0 mg) was added at 0 ° C. The mixture was stirred at the same temperature for 30 minutes and further at room temperature for 2 hours. The reaction solution was poured into water, extracted with ethyl acetate, washed with saturated saline, and dried over sodium sulfate. The solvent was distilled off, and the obtained residue was purified by thin-layer chromatography (eluent: ethyl acetate / hexane = 1/4) to obtain the title compound (57.0 g, yield 67.0%). Was. ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.88 (2H, s), 5.07 (2H, s),
4.19 (2H, q, J = 8.8), 2.26 (3H, s), 2.09 (6H, s),
1.46 (6H, s). Physical properties: crystals (melting point: 140-141 ° C).

[0291]

Example 12 3,3-dimethylbutyric acid =
5,5-dimethyl-1-cyanomethoxy-2-oxo-
3- (2,4,6-trimethylphenyl) -2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 1-169) (1) 3,3-dimethylbutyric acid = 5.5
-Dimethyl-1-hydroxy-2-oxo-3- (2,
4,6-trimethylphenyl) -2,5-dihydro-1
H-pyrrol-4-yl ester (Compound No. 1-
5, Step D-1) 3,3-dimethylbutyric acid produced according to Example 4 = 5,5-dimethyl-1-methoxymethoxy-
2-oxo-3- (2,4,6-trimethylphenyl)
To a dichloromethane solution (20 ml) of -2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 1-111) (3.47 g) was added trimethylsilane bromide (11.4 ml) and molecular sieve 3A. Was added at 0 ° C., and the mixture was stirred at room temperature for 3.5 hours. After completion of the reaction, the reaction solution was poured into aqueous sodium hydrogen carbonate, extracted with ethyl acetate, washed with saturated saline, and dried over magnesium sulfate. The solvent was distilled off, and the obtained residue was purified by silica gel column chromatography (elution solvent: ethyl acetate / hexane = 1/3) to obtain the title compound (2.12 g, yield 68.6%). Was. ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.81 (2H, s), 2.23 (3H, s),
2.17 (2H, s), 2.13 (6H, s), 1.44 (6H, s), 0.82 (9
H, s). Physical properties: Crystal (melting point: 185-190 ° C). (2) 3,3-dimethylbutyric acid = 5,5
-Dimethyl-1-cyanomethoxy-2-oxo-3-
(2,4,6-trimethylphenyl) -2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 1-169, Step D-2) Sodium hydride (34.0 mg in 60% mineral oil) ) In dimethylformamide solution (2 ml), 3,3-dimethylbutyric acid obtained in (1) = 5,5
-Dimethyl-1-methoxymethoxy-2-oxo-3-
(2,4,6-trimethylphenyl) -2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 1-111) (201.7 mg) and bromoacetonitrile (0.11 g) were added at 0 ° C. The mixture was stirred at room temperature for 1 hour. The reaction solution was poured into water, extracted with ethyl acetate, washed with brine, and dried over magnesium sulfate.
The solvent was distilled off, and the obtained residue was purified by thin-layer chromatography (elution solvent: ethyl acetate / hexane = 1/3) to obtain the title compound (155.8 mg, yield 69.8%). Was. ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.84 (2H, s), 4.90 (2H, s),
2.24 (3H, s), 2.19 (2H, s), 2.15 (6H, s), 1.54 (6H,
s), 0.83 (9H, s). Physical properties: crystals (melting point: 81-82 ° C).

[0292]

Example 13 3,3-dimethylbutyric acid =
5,5-dimethyl-1-methoxycarbonyloxy-2
-Oxo-3- (2,4,6-trimethylphenyl)-
2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 1-224, Step D-2) 3,3-dimethylbutyric acid obtained according to Example 12 (1) = 5,5- Dimethyl-1-hydroxy-
2-oxo-3- (2,4,6-trimethylphenyl)
Methyl chlorocarbonate (0.05 ml) and triethylamine (0. .10ml)
Was added at 0 ° C., and the mixture was stirred at room temperature for 1.5 hours. The reaction solution was poured into water, extracted with ethyl acetate, washed with brine, and dried over magnesium sulfate. Evaporate the solvent,
The obtained residue was purified by thin-layer chromatography (eluent: ethyl acetate / hexane = 1/3) to give the title compound (171.0 mg, yield 91.0%). ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.83 (2H, s), 3.95 (3H, s),
2.24 (3H, s), 2.19 (2H, s), 2.17 (6H, s), 1.10 (6
H, s), 0.83 (9H, s). Physical properties: Crystal (melting point: 138-141 ° C).

[0293]

EXAMPLE 14 Carbonic acid methyl ester 1-ethylthio-5,5-dimethyl-4-methoxycarbonyl-2-
Oxo-3- (2,4,6-trimethylphenyl)-
2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 5-94) (1) Carbonic acid = methyl ester = 5,5-dimethyl-
4-methoxycarbonyl-2-oxo-3- (2,4,
6-trimethylphenyl) -2,5-dihydro-1H-
Pyrrole-4-yl ester 5,5-dimethyl-4-hydroxy-2-oxo-3-
(2,4,6-trimethylphenyl) -2,5-dihydro-1H-pyrrole (0.70 g) and triethylamine (0.60 ml) in dichloromethane (14 ml)
To this was added methyl chlorocarbonate (0.25 ml) at 0 ° C. The mixture was stirred at the same temperature for 1 hour and subsequently at room temperature for 1 hour. After completion of the reaction, dichloromethane was added, the dichloromethane layer was separated, washed with water, and dried over magnesium sulfate. The solvent was distilled off, and the obtained residue was subjected to silica gel column chromatography (elution solvent: ethyl acetate / hexane =
1/10) to give the title compound (0.66 g, yield 76.3%). ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.87 (2H, s), 6.45 (1H, br
d), 3.61 (3H, s), 2.26 (3H, s), 2.17 (6H, s), 1.50
(6H, s). Physical properties: crystals (melting point: 135-137 ° C). (2) Carbonic acid = methyl = ester = 1-ethylthio-
5,5-dimethyl-4-methoxycarbonyl-2-oxo-3- (2,4,6-trimethylphenyl) -2,5
-Dihydro-1H-pyrrol-4-yl ester (Compound No. 5-94, Step E) Carbonic acid methyl ester obtained by (1) = 5.5
-Dimethyl-4-methoxycarbonyl-2-oxo-3
-(2,4,6-trimethylphenyl) -2,5-dihydro-1H-pyrrolepyrrol-4-yl ester (0.66 g), N-ethylthioisoindole-1,
3-dione (0.45 g) and potassium carbonate (0.3
The acetone solution (7 ml) of g) was treated with ultrasonic waves for 1.5 hours. After the completion of the reaction, the reaction solution was poured into water and extracted with ethyl acetate. After washing with saturated saline, it was dried over magnesium sulfate. The solvent was distilled off, and the obtained residue was purified by silica gel column chromatography (elution solvent: ethyl acetate / hexane = 1/10) to give the title compound (0.66).
g, 80.5% yield). ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.86 (2H, s), 3.60 (3H, s),
2.89 (2H, q, J = 7.3), 2.26 (3H, s), 2.14 (6H, s),
1.49 (6H, s), 1.28 (3H, t, J = 7.3). Physical properties: amorphous.

[0294]

EXAMPLE 15 Carbonic acid 3-chloro-2,2-dimethylpropyl ester = 5,5-dimethyl-1-ethylsulfinyl-2-oxo-3- (2,4,6-trimethylphenyl) -2, 5-dihydro-1H-pyrrole-4-
Il = ester (Compound No. 7-22) and carbonic acid = 3-
Chloro-2,2-dimethylpropyl ester = 5.5
-Dimethyl-1-ethylsulfonyl-2-oxo-3-
(2,4,6-trimethylphenyl) -2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 7-30) (1) 1-ethylthio-5,5-dimethyl-4-hydroxy- 2-oxo-3- (2,4,6-trimethylphenyl) -2,5-dihydro-1H-pyrrole (Compound No. 5-79, Step H) Carbonic acid methyl ester prepared according to Example 14
-Ethylthio-5,5-dimethyl-2-oxo-3-
Ethanol solution (4 ml) of (2,4,6-trimethylphenyl) -2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 5-94) (0.59 g)
To the mixture was added a 1N aqueous sodium hydroxide solution (1.65 ml), and the mixture was stirred at 0 ° C for 10 minutes and at room temperature for 30 minutes. The reaction solution was neutralized by adding a 1N aqueous hydrochloric acid solution, and extracted with ethyl acetate. After washing with saturated saline, it was dried with magnesium sulfate. The solvent was distilled off, and the obtained residue was purified by silica gel column chromatography (eluent: ethyl acetate / hexane = 1/4) to give the title compound (412.1 m).
g, yield 83.8%). ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.90 (2H, s), 6.80 (1H, brd.
s), 2.82 (2H, q, J = 7.4), 2.27 (3H, s), 2.11 (6H,
s), 1.47 (6H, s), 1.25 (3H, t, J = 7.4). Physical properties: crystals (melting point: 142-145 ° C). (2) Carbonic acid = 3-chloro-2,2-dimethylpropyl = ester = 5,5-dimethyl-1-ethylthio-2-
Oxo-3- (2,4,6-trimethylphenyl)-
2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 5-106, step A-3) 3-chloro-2,2-dimethylpropanol (164.
9mg) in dichloromethane solution (1ml), triphosgene (130.0mg) and pyridine (0.12ml)
Was added at 0 ° C., and the mixture was stirred at the same temperature for 45 minutes. The reaction solution was treated with 1-ethylthio-5,5-dimethyl-4-hydroxy-2-oxo-3- (2,4,
6-trimethylphenyl) -2,5-dihydro-1H-
Pyrrole (Compound No. 5-79) (197.8 mg) and triethylamine (0.185 ml) were added to a dichloromethane solution (2 ml) at 0 ° C., and the mixture was stirred at the same temperature for 1 hour. After the completion of the reaction, the reaction solution was poured into water and extracted with ethyl acetate. The organic layer was washed with brine and dried over magnesium sulfate. The solvent was distilled off, and the obtained residue was purified by thin-layer chromatography (eluent: ethyl acetate / hexane = 1/4) to give the title compound (249.4 mg,
Yield 84.5%). ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.84 (2H, s), 3.85 (2H, s),
3.21 (2H, s), 2.89 (5H, q, J = 7.3), 2.24 (3H, s),
2.15 (6H, s), 1.56 (6H, s), 1.28 (6H, t, J = 7.3),
0.84 (9H, s). Physical properties: oil. (3) Carbonic acid = 3-chloro-2,2-dimethylpropyl = ester = 5,5-dimethyl-1-ethylsulfinyl-2-oxo-3- (2,4,6-trimethylphenyl) -2,5- Dihydro-1H-pyrrol-4-yl =
Ester (Compound No. 7-22) and carbonic acid = 3-chloro-2,2-dimethylpropyl = ester = 5,5-dimethyl-1-ethylsulfonyl-2-oxo-3- (2,
4,6-trimethylphenyl) -2,5-dihydro-1
H-pyrrol-4-yl ester (Compound No. 7-3)
0) (Step F) Carbonic acid = 3-chloro-2,2-dimethylpropyl = ester obtained by (2) = 5,5-dimethyl-1-ethylthio-2-oxo-3- (2,4,6) -Trimethylphenyl) -2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 5-106) (110.0 m
To a solution of g) in 1,2-dichloroethane (5 ml) was added 3-chloroperbenzoic acid, and the mixture was stirred at room temperature for 4 hours. The reaction solution was poured into aqueous sodium hydrogen carbonate and extracted with ethyl acetate. After washing with saturated saline, it was dried with magnesium sulfate. The solvent was distilled off, and the obtained residue was purified by thin-layer chromatography (eluent: ethyl acetate / hexane = 1/3) to give the title compound, 3-chloro-2,2-dimethylpropyl carbonate. = Ester = 5,5-dimethyl-1-ethylsulfinyl-2-oxo-3- (2,4,6-trimethylphenyl) -2,5-dihydro-1H-pyrrole-4-
Il = ester (Compound No. 7-22, 90.0 mg,
Yield = 77.2%) and carbonic acid = 3-chloro-2,2-dimethylpropyl = ester = 5,5-dimethyl-1-ethylsulfonyl-2-oxo-3- (2,4,6-trimethylphenyl) -2,5-dihydro-1H-pyrrole-
4-yl ester (Compound No. 7-30, 18.2 m
g, yield 16.1%).

Carbonic acid 3-chloro-2,2-dimethylpropyl ester = 5,5-dimethyl-1-ethylsulfinyl-2-oxo-3- (2,4,6-trimethylphenyl) -2,5- Dihydro-1H-pyrrol-4-yl ester: ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.85 (2H, s), 4.18-4.00 (1H,
m), 3.84 (2H, s), 3.60-3.42 (1H, m), 3.21 (2H,
s), 2.24 (3H, s), 2.183 (3H, s), 2.15 (3H, s), 1.80
(3H, s), 1.53 (3H, s), 1.29 (3H, t, J = 7.7), 0.84
(9H, s). Physical properties: oil.

Carbonic acid 3-chloro-2,2-dimethylpropyl ester = 5,5-dimethyl-1-ethylsulfonyl-2-oxo-3- (2,4,6-trimethylphenyl) -2,5- Dihydro-1H-pyrrol-4-yl ester: ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.86 (2H, s), 3.84 (2H, s),
3.61 (2H, q, J = 7.3), 3.21 (2H, s), 2.25 (3H, s),
2.15 (6H, s), 1.80 (6H, s), 1.40 (3H, t, J = 7.3),
0.84 (6H, s). Physical properties: oil.

[0297]

Example 16 3- (2,6-dimethylphenyl) -4
-Hydroxy-1-methoxy-1-azaspiro [4,
5] Decane-3-ene-2,8-dione (Compound No. 1
1-37) (1) 4,4-Ethylenedioxy-1-hydroxyaminocyclohexanecarboxylic acid ethyl ester Diisopropylamine (1.55 ml) was dissolved in tetrahydrofuran (10 ml). -78 ° C
Hexane solution (1.54 mol / L, 7 ml) of n-butyl lithium and 1,3-dimethyl-3,4,5,6-tetrahydro-2 (1H) -pyrimidinone (1.36 ml) at the same temperature. ) In order, and added at −78 ° C. for 0.5
Stirred for hours. Next, a tetrahydrofuran solution (3 ml) of 4,4-ethylenedioxycyclohexanecarboxylic acid ethyl ester (1.78 g) was added to the reaction solution, and the mixture was stirred at -78 ° C for 1 hour. Furthermore,
1-Chloro-1-nitrosocyclohexane (1.63 g) was added to the reaction solution, and the mixture was stirred at -78 ° C for 1 hour. Further, hydrochloric acid (1 mol / L, 16 ml) was added to the reaction solution, and the mixture was stirred at room temperature for 1 hour. After completion of the reaction, sodium hydrogen carbonate was added to the reaction solution to adjust the pH to 9, followed by extraction with ethyl acetate. The organic layer was washed with saturated saline and dried over magnesium sulfate. The solvent was distilled off, and the obtained residue was purified by silica gel column chromatography (elution solvent: ethyl acetate / hexane = 1/4) to obtain the title compound (1.47 g, yield 72.3%). Was. ¹ H-NMR (CDCl ₃ ) δ (ppm): 4.22 (2H, q, J = 7.1), 3.95 (4
H, s), 2.20-2.00 (2H, m), 1.95-1.78 (4H, m), 1.70-
1.59 (2H, m), 1.29 (3H, t, J = 7.1). (2) 4,4-ethylenedioxy-1- {N- (2,
6-dimethylphenylacetyl) -N-hydroxyamino dicyclohexanecarboxylic acid ethyl ester (Step A-2) 4,4-ethylenedioxy-1- obtained by (1)
Hydroxyaminocyclohexanecarboxylic acid ethyl ester (1.47 g) and sodium hydrogen carbonate (0.75 g) were added to a mixed solvent of ethyl acetate (8 ml) -water (10 ml). 2,6-
A solution of dimethylphenylacetic acid chloride (1.21 g) in ethyl acetate (8 ml) was added dropwise at 0 ° C., and the mixture was stirred at 0 ° C. for 1 hour and at room temperature for 3 hours. The organic layer was separated, washed with saturated saline, and dried over magnesium sulfate. After the solvent was distilled off, the obtained residue was subjected to silica gel column chromatography (elution solvent: ethyl acetate /
Hexane = 1/4) to give the title compound (0.77
g, yield 32.8%). ¹ H-NMR (DMSO-d ₆ ) δ (ppm): 10.06 (1H, s), 6.98 (3H,
s), 4.01 (2H, q, J = 7.1), 3.87 (4H, s), 3.77 (2H,
s), 2.50-1.65 (8H, s), 2.15 (6H, s), 1.11 (3H, t, J
= 7.1). (3) 4-oxo-1- {N- (2,6-dimethylphenylacetyl) -N-hydroxyamino} cyclohexanecarboxylic acid ethyl ester (Step I-1) 4, obtained by (2) 4-ethylenedioxy-1-
{N- (2,6-Dimethylphenylacetyl) -N-hydroxyamino} cyclohexanecarboxylic acid ethyl ester (6.00 g) was dissolved in tetrahydrofuran (80 ml). Hydrochloric acid (1 mol / L, 60 ml) was added to the reaction solution, and 1.5 hours at 60 ° C.
Stirred for hours. A saturated saline solution was added to the reaction solution, and the mixture was extracted with ethyl acetate. After washing the organic layer with saturated saline,
Dried over magnesium sulfate. After the solvent was distilled off, the obtained solid residue was mixed with a diethyl ether-hexane mixed solvent (1: 1).
Washed with 1) to give the title compound (4.40 g, yield 82.8).
%). ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.09-7.00 (3H, m), 6.53 (1H,
brd.s), 4.24 (2H, q, J = 7.1), 3.98 (2H, s), 2.90-2.
20 (8H, m), 2.29 (6H, s), 1.29 (3H, t, J = 7.1). (4) 4- (N-methoxyimino) -1- {N-
(2,6-dimethylphenylacetyl) -N-hydroxyamino {cyclohexanecarboxylic acid =
Ethyl ester (Step 1-2) 4-oxo-1- {N- (2,6) obtained by (3)
-Dimethylphenylacetyl) -N-hydroxyamino dicyclohexanecarboxylic acid ethyl ester (0.34 g) was dissolved in ethanol (5 ml). O-methylhydroxylamine hydrochloride (0.16 g) and tetrahydrofuran (2 m
l) was added in order, and the mixture was stirred at room temperature for 1 hour. A saturated saline solution was added to the reaction solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine and dried over magnesium sulfate.
After evaporating the solvent, the residue was purified by silica gel column chromatography (eluent: ethyl acetate / hexane = 1/4) to obtain the title compound (0.30 g, yield 80.0%). ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.05-7.04 (3H, m), 6.36 (1H,
brd.s), 4.21 (2H, q, J = 7.0), 3.95 (2H, s), 3.83 (3
H, s), 3.10-1.80 (8H, m), 2.27 (6H, s), 1.26 (3H,
t, J = 7.0). (5) 3- (2,6-dimethylphenyl) -4-hydroxy-1-methoxy-8- (N-methoxyimino)-
1-Azaspiro [4,5] decane-3-en-2-one (Compound No. 11-37, A-2) Sodium hydride (22.9 mg in 60% mineral oil) is dissolved in dimethylformamide (10 ml). And cooled to 0 ° C. At the same temperature, 4- (N-methoxyimino) -1- {N- (2,6) obtained in (4) was added to this solution.
-Dimethylphenylacetyl) -N-hydroxyamino dicyclohexanecarboxylic acid ethyl ester (179.5 mg, 0.447 mmol) and methyl iodide (0.036 ml) were added, and the mixture was added at room temperature.
Stirred for hours. At 0 ° C., potassium tert-butoxide (80.3 mg) was added, and the mixture was stirred at room temperature for 6 hours. After the reaction solution was poured into water and washed with diethyl ether, the aqueous layer was acidified with concentrated hydrochloric acid and extracted with ethyl acetate.
The organic layer was washed with brine and dried over magnesium sulfate. After the solvent was distilled off, the residue was subjected to silica gel column chromatography (elution solvent: ethyl acetate / hexane = 3 /
1) to give the title compound (128.3 mg, yield 7).
8.1%). ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.06-6.89 (3H, m), 3.81 (3
H, s), 3.78 (3H, s), 2.85-2.43 (4H, m), 2.13-1.83
(4H, m), 2.00 (6H, s). Physical properties: gum-like.

Further, the following compounds were produced according to the above Examples 1 to 16.

[0299]

Example 17 2-Methylpropionic acid =
5,5-dimethyl-1-methoxy-2-oxo-3-
(2,4,6-trimethylphenyl) -2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 1-17) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.83 (2H, s), 4.00 (2H, s),
2.55 (1H, septet, J = 7.0), 2.24 (3H, s), 2.16 (6H,
s), 1.48 (6H, s), 1.01 (6H, d, J = 7.0). Physical properties: crystals (melting point: 94-95 ° C).

[0300]

Example 18 2-chlorobenzoic acid = 5
5-dimethyl-1-methoxy-2-oxo-3- (2,
4,6-trimethylphenyl) -2,5-dihydro-1
H-pyrrol-4-yl ester (Compound No. 1-2
2) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.60-7.56 (1H, m), 7.46-7.43
(2H, m), 7.33-7.24 (1H, m), 6.83 (2H, s), 4.04 (3
H, s), 2.22 (9H, s), 1.58 (6H, s). Physical properties: crystals (melting point: 143-145 ° C).

[0301]

EXAMPLE 19 2-Methylacrylic acid = 5,5-dimethyl-1-methoxy-2-oxo-3- (2,4,6-trimethylphenyl) -2,5-dihydro-1H-pyrrole-4- Il = ester (Compound No. 1-24) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.83 (2H, s), 6.14 (1H, t, J
= 1.0), 5.66 (1H, t, J = 1.5), 4.01 (3H, s), 2.24 (3
H, s), 2.17 (6H, s), 1.84 (3H, t, J = 1.1), 1.51 (6
H, s). Physical properties: Crystal (melting point: 92-95 ° C).

[0302]

Example 20 2-phenoxyacetic acid = 5,5-dimethyl-1-methoxy-2-oxo-3- (2,4,6-trimethylphenyl) -2,5-dihydro-1H-pyrrol-4-yl = Ester (Compound No. 1-26) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.21 -7.13 (2H, m), 7.01-6.9
3 (1H, m), 6.86 (2H, s), 6.57-6.51 (2H, m), 4.60
(2H, s), 3.99 (3H, s), 2.29 (3H, s), 2.13 (6H, s),
1.47 (6H, s). Physical properties: crystals (melting point: 124-127 ° C).

[0303]

Example 21 3,3-dimethylbutyric acid =
5,5-dimethyl-1-methoxy-2-oxo-3-
(2,4,6-trimethylphenyl) -2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 1-27) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.81 (2H, s), 4.00 (3H, s),
2.23 (3H, s), 2.17 (2H, s), 2.15 (6H, s), 1.48 (6
H, s), 0.83 (9H, s). Physical properties: oil.

[0304]

Example 22 Carbonic acid methyl ester = 5,5-dimethyl-1-methoxy-2-oxo-3- (2,4,6-
(Trimethylphenyl) -2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 1-28) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.86 (2H, s), 4.00 (3H, s),
3.61 (3H, s), 2.26 (3H, s), 2.16 (6H, s), 1.53 (6
H, s). Physical properties: oil.

[0305]

Example 23 Isobutyl carbonate = ester = 5,5-
Dimethyl-1-methoxy-2-oxo-3- (2,4,
6-trimethylphenyl) -2,5-dihydro-1H-
Pyrrole-4-yl ester (Compound No. 1-33) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.84 (2H, s), 4.00 (3H, s),
3.74 (2H, d, J = 6.6), 2.25 (3H, s), 2.17 (6H, s),
1.63-1.80 (1H, m), 1.53 (6H, s), 0.77 (6H, d, J = 7.
0). Physical properties: oil.

[0306]

Example 24 Carbonic acid = cyclopentyl = ester = 5
5-dimethyl-1-methoxy-2-oxo-3- (2,
4,6-trimethylphenyl) -2,5-dihydro-1
H-pyrrol-4-yl ester (Compound No. 1-3
5) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.85 (2H, s,), 4.83-4.81 (1
H, m), 4.00 (3H, s), 2.25 (3H, s), 2.17 (6H, s),
1.62-1.36 (8H, m), 1.52 (6H, s). Physical properties: oil.

[0307]

Example 25 Carbonic acid = tetrahydrofuran-2-ylmethyl ester = 5,5-dimethyl-1-methoxy-2
-Oxo-3- (2,4,6-trimethylphenyl)-
2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 1-39) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.85 (2H, s), 4.14 (2H, s),
4.00 (3H, s), 3.95-3.70 (3H, m), 2.25 (3H, s), 2.1
7 (6H, s), 2.40-1.80 (4H, m), 1.53 (6H, s). Physical properties: oil.

[0308]

Example 26 Carbonic acid 3-chloro-2,2-dimethylpropyl ester = 5,5-dimethyl-1-methoxy-
2-oxo-3- (2,4,6-trimethylphenyl)
-2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 1-40) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.85 (2H, s), 4.01 (3H, s),
3.85 (2H, s), 3.22 (2H, s), 2.25 (3H, s), 2.17 (6
H, s), 1.54 (6H, s), 0.85 (6H, s). Physical properties: crystals (melting point: 84-85 ° C).

[0309]

Example 27 Carbonic acid = 1,2-dimethylpropyl ester = 5,5-dimethyl-1-methoxy-2-oxo-
3- (2,4,6-trimethylphenyl) -2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 1-41) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.83 ( 2H, s), 4.33 (1H, m),
2.23 (3H, s), 2.17 (6H, s), 1.70-1.53 (1H, m), 1.5
8 (6H, s), 0.97 (3H, d, J = 5.9), 0.74 (6H, dd, J = 6.
6, 1.5). Physical properties: oil.

[0310]

Example 28 Carbonic acid = S-methyl ester = 5,5-
Dimethyl-1-methoxy-2-oxo-3- (2,4,
6-trimethylphenyl) -2,5-dihydro-1H-
Pyrrole-4-yl ester (Compound No. 1-42) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.85 (2H, s), 3.99 (3H, s),
2.26 (3H, s), 2.20 (3H, s), 2.16 (6H, s), 1.51 (6
H, s). Physical properties: oil.

[0311]

Example 29 O-phenyl thiocarbonate = ester =
5,5-dimethyl-1-methoxy-2-oxo-3-
(2,4,6-trimethylphenyl) -2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 1-49) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.36-7.20 ( 3H, m), 6.89 (2H,
s), 6.59-6.64 (2H, m), 4.02 (3H, s), 2.30 (3H,
s), 2.20 (6H, s), 1.63 (6H, s). Physical properties: oil.

[0312]

Example 30 Dithiocarbonate = S-propyl ester =
O- [5,5-dimethyl-1-methoxy-2-oxo-
3- (2,4,6-trimethylphenyl) -2,5-dihydro-1H-pyrrol-4-yl] ester (Compound No. 1-52) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.80 ( 2H, s), 4.00 (3H, s),
2.95 (2H, t, J = 7.1), 2.23 (3H, s), 2.17 (6H, s),
1.56 (6H, s), 1.42-1.60 (2H, m), 0.90 (3H, t, J = 7.
Five). Physical properties: oil.

[0313]

Example 31 S-isopropyl dithiocarbonate = ester O- [5,5-dimethyl-1-methoxy-2-oxo-3- (2,4,6-trimethylphenyl) -2,5
-Dihydro-1H-pyrrol-4-yl] ester (Compound No. 1-53) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.80 (2H, s), 3.53 (3H, s),
3.46 (1H, septet, J = 6.7), 2.22 (3H, s), 2.17 (6H,
s), 1.55 (6H, s), 1.22 (3H, d, J = 6.7). Physical properties: oil.

[0314]

Example 32 Dithiocarbonate = S-butyl ester = O
-[5,5-dimethyl-1-methoxy-2-oxo-3
-(2,4,6-trimethylphenyl) -2,5-dihydro-1H-pyrrol-4-yl] ester (Compound No. 1-54) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.08 (2H , s), 4.00 (3H, s),
2.97 (2H, t, J = 7.0), 2.23 (3H, s), 2.17 (6H, s),
1.56 (6H, s), 1.56-1.23 (4H, m), 0.86 (3H, t, J = 7.
3). Physical properties: oil.

[0315]

Example 33 Dithiocarbonate = S-phenyl = ester =
O- [5,5-dimethyl-1-methoxy-2-oxo-
3- (2,4,6-trimethylphenyl) -2,5-dihydro-1H-pyrrol-4-yl] ester (Compound No. 1-57) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.26- 7.44 (5H, m), 6.83 (2H,
s), 3.98 (3H, s), 2.28 (3H, s), 2.09 (6H, s), 1.4
9 (6H, s). Physical properties: Crystal (melting point: 160-164 ° C).

[0316]

Example 34 5,5-Dimethyl-1-ethoxy-4-
Hydroxy-2-oxo-3- (2,4,6-trimethylphenyl) -2,5-dihydro-1H-pyrrole (Compound No. 1-71) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.80 ( 2H, s), 4.07 (2H, q, J
= 7.2), 2.23 (3H, s), 2.06 (6H, s), 1.41 (6H, s),
1.28 (3H, t, J = 7.2). Physical properties: crystals (melting point: 169-171 ° C).

[0317]

Example 35 2,2-Dimethylpropionic acid = 5,5-dimethyl-1-ethoxy-2-oxo-3
-(2,4,6-trimethylphenyl) -2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 1-72) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.81 (2H , s), 4.21 (2H, q, J =
7.0), 2.24 (3H, s), 2.15 (6H, s), 1.47 (6H, s), 1.
36 (3H, t, J = 7.0), 1.07 (9H, s). Physical properties: oil.

[0318]

Example 36: Dithiocarbonate = S-ethyl = ester = O
-[5,5-dimethyl-1-ethoxy-2-oxo-3
-(2,4,6-trimethylphenyl) -2,5-dihydro-1H-pyrrol-4-yl] ester (Compound No. 1-74) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.80 (2H , s), 4.22 (2H, q, J
= 7.0), 2.98 (2H, q, J = 7.3), 2.23 (3H, s), 2.17 (6
H, s), 1.55 (6H, s), 1.36 (3H, t, J = 7.3), 1.17 (3
H, t, J = 7.3). Physical properties: oil.

[0319]

Example 37 5,5-Dimethyl-1-propyloxy-4-hydroxy-2-oxo-3- (2,4,6-trimethylphenyl) -2,5-dihydro-1H-pyrrole (Compound No. 1) -75) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.88 (2H, s), 6.70 (1H, brd.
s), 4.08-4.01 (2H, m), 2.27 (3H, s), 2.12 (6H, s),
1.80-1.69 (2H, m), 1.49 (6H, s), 1.01 (3H, t, J = 7.
2). Physical properties: crystals (melting point: 133-134 ° C).

[0320]

Example 38 2,2-Dimethylpropionic acid = 5,5-dimethyl-1-propyloxy-2-oxo-3- (2,4,6-trimethylphenyl) -2,5
-Dihydro-1H-pyrrol-4-yl ester (Compound No. 1-76) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.81 (2H, s), 4.12 (2H, t, J
= 6.6), 2.24 (3H, s), 2.16 (6H, s), 1.87-1.69 (1H,
m), 1.47 (6H, s), 1.07 (9H, s), 1.03 (3H, t, J = 7.3
3). Physical properties: oil.

[0321]

Example 39: S-ethyl dithiocarbonate = ester = O
-[5,5-dimethyl-1-propyloxy-2-oxo-3- (2,4,6-trimethylphenyl) -2,5
-Dihydro-1H-pyrrol-4-yl] ester (Compound No. 1-78) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.80 (2H, s), 4.12 (2H, t, J
= 6.6), 2.97 (2H, q, J = 7.7), 2.22 (3H, s), 2.16 (6
H, s), 1.87-1.69 (2H, m), 1.55 (6H, s), 1.16 (3H,
t, J = 7.7), 1.03 (3H, t, J = 7.3). Physical properties: oil.

[0322]

Example 40 5,5-Dimethyl-1-isopropyloxy-4-hydroxy-2-oxo-3- (2,4,6
-Trimethylphenyl) -2,5-dihydro-1H-pyrrole (Compound No. 1-79) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.88 (2H, m), 6.55 (1H, brd.
s), 4.23-4.24 (1H, m), 2.27 (3H, s), 2.12 (6H, s),
1.47 (6H, s), 1.31 (6H, d, J = 6.2). Physical properties: crystals (melting point: 156-158 ° C).

[0323]

Example 41 5,5-Dimethyl-1-allyloxy-
4-Hydroxy-2-oxo-3- (2,4,6-trimethylphenyl) -2,5-dihydro-1H-pyrrole (Compound No. 1-83) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.89 (2H, s), 6.69 (1H, brd.
s), 6.30-6.00 (1H, m), 5.39-5.25 (2H, m), 5.30 (1H,
d, J = 1.8), 4.58 (2H, d, J = 5.9), 2.27 (3H, s), 2.12
(6H, s), 1.48 (6H, s). Physical properties: crystals (melting point: 130-133 ° C).

[0324]

Example 42 2,2-Dimethylpropionic acid = 5,5-dimethyl-1-allyloxy-2-oxo-3- (2,4,6-trimethylphenyl) -2,5-
Dihydro-1H-pyrrol-4-yl ester (Compound No. 1-84) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.81 (2H, s), 6.19-5.97 (1H,
m), 5.42-5.27 (2H, m), 4.66-4.62 (2H, m), 2.24 (3
H, s), 2.15 (6H, s), 1.46 (6H, s), 1.07 (9H, s). Physical properties: oil.

[0325]

Example 43 Dithiocarbonate = S-ethyl = ester = O
-[5,5-dimethyl-1-allyloxy-2-oxo-3- (2,4,6-trimethylphenyl) -2,5-
Dihydro-1H-pyrrol-4-yl] ester (Compound No. 1-86) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.80 (2H, s), 6.19-5.97 (1H,
m), 5.42-5.27 (2H, m), 4.66-4.62 (2H, m), 2.97 (2
H, q, J = 7.3), 2.23 (3H, s), 2.16 (6H, s), 1.56 (6
H, s), 1.16 (3H, t, J = 7.3). Physical properties: oil.

[0326]

Example 44 5,5-Dimethyl-1-propargyloxy-4-hydroxy-3- (2,4,6-trimethylphenyl) -2,5-dihydro-1H-pyrrole-2-
ON (Compound No. 1-87) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.90 (2H, s), 4.72 (2H, d, J
= 2.4), 2.55 (1H, t, J = 2.5), 2.27 (3H, s), 2.12 (6
H, s), 1.52 (6H, s). Physical properties: crystals (melting point: 172-175 ° C).

[0327]

Example 45 2,2-Dimethylpropionic acid = 5,5-dimethyl-1-propargyloxy-2-
Oxo-3- (2,4,6-trimethylphenyl)-
2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 1-88) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.82 (2H, s), 4.79 (2H, d, J
= 2.6), 2.24 (3H, s), 2.15 (6H, s), 1.51 (6H, s),
1.07 (9H, s). Physical properties: oil.

[0328]

Example 46 Dithiocarbonate = S-ethyl = ester = O
-[5,5-dimethyl-1-propargyloxy-2-
Oxo-3- (2,4,6-trimethylphenyl)-
2,5-Dihydro-1H-pyrrol-4-yl] ester (Compound No. 1-90) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.80 (2H, s), 4.79 (2H, d, J
= 2.2), 2.97 (2H, q, J = 7.5), 2.58 (1H, t, J = 2.6),
2.23 (3H, s), 2.16 (6H, s), 1.58 (6H, s), 1.16 (3H,
t, J = 7.5). Physical properties: oil.

[0329]

Example 47 5,5-Dimethyl-1-cyclohexylmethyloxy-4-hydroxy-2-oxo-3-
(2,4,6-trimethylphenyl) -2,5-dihydro-1H-pyrrole (Compound No. 1-91) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.88 (2H, s), 3.92-3.88 (2H,
m), 2.27 (3H, s), 2.11 (6H, s), 1.91-0.97 (11H,
m), 1.47 (6H, s). Physical properties: crystals (melting point: 195-197 ° C).

[0330]

Example 48 2,2-Dimethylpropionic acid = 5,5-dimethyl-1-cyclohexylmethyloxy-2-oxo-3- (2,4,6-trimethylphenyl) -2,5-dihydro- 1H-pyrrol-4-yl =
Ester (Compound No. 1-92) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.81 (2H, s), 3.97 (2H, d, J
= 6.2), 2.23 (3H, s), 2.15 (6H, s), 1.96-1.18 (11H,
m), 1.47 (6H, s), 1.07 (9H, s). Physical properties: oil.

[0331]

Example 49 S-ethyl dithiocarbonate = ester = O
-[5,5-Dimethyl-1-cyclohexylmethyloxy-2-oxo-3- (2,4,6-trimethylphenyl) -2,5-dihydro-1H-pyrrol-4-yl]
Ester (Compound No. 1-94) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.79 (2H, s), 3.97 (2H, d,
J = 6.23), 2.97 (2H, q, J = 7.3), 2.22 (3H, s), 2.17 (6
H, s), 2.30-1.00 (11H, m), 1.54 (6H, s), 1.16 (3H,
t, J = 7.3). Physical properties: oil.

[0332]

Example 50 5,5-Dimethyl-1-benzyloxy-4-hydroxy-2-oxo-3- (2,4,6-trimethylphenyl) -2,5-dihydro-1H-pyrrole (Compound No. 1) −95) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.47-7.35 (5H, m), 6.91 (2H,
s), 6.21 (1H, brd.s), 5.12 (2H, s), 2.28 (3H, s),
2.15 (6H, s), 1.32 (6H, s). Physical properties: crystals (melting point: 173-177 ° C).

[0333]

Example 51 Cyclohexylcarboxylic acid = 5,5-dimethyl-1-methoxymethoxy-2-oxo-3-
(2,4,6-trimethylphenyl) -2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 1-106) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.83 (2H, s), 5.05 (2H, s),
3.61 (3H, s), 2.24 (3H, s), 2.15 (6H, s), 2.39-2.3
0 (1H, m), 1.97-1.19 (10H, m). Physical properties: oil.

[0334]

Example 52 3-Chloro-2,2-dimethylpropionic acid = 5,5-dimethyl-1-methoxymethoxy-2-oxo-3- (2,4,6-trimethylphenyl) -2,5 -Dihydro-1H-pyrrol-4-yl ester (Compound No. 1-112) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.82 (2H, s), 5.06 (2H, s),
3.61 (3H, s), 3.52 (2H, s), 2.23 (3H, s), 2.16 (6
H, s), 1.51 (6H, s), 1.10 (6H, s). Properties: Oil

[0335]

Example 53 Carbonic acid = 2,2-dimethylpropyl ester = 5,5-dimethyl-1-methoxymethoxy-2-
Oxo-3- (2,4,6-trimethylphenyl)-
2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 1-123) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.83 (2H, s), 5.06 (2H, s),
3.67 (2H, s), 3.61 (3H, s), 2.24 (3H, s), 2.17 (6
H, s), 1.54 (6H, s), 0.78 (9H, s). Physical properties: oil.

[0336]

Example 54: Dithiocarbonate = S-ethyl = ester = O
-[5,5-dimethyl-1-methoxymethoxy-2-oxo-3- (2,4,6-trimethylphenyl) -2,
5-Dihydro-1H-pyrrol-4-yl] ester (Compound No. 1-128) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.80 (2H, s), 5.06 (2H, s),
3.61 (3H, s), 2.98 (2H, q, J = 7.3), 2.23 (3H, s),
2.17 (6H, s), 1.56 (6H, s), 1.16 (3H, t, J = 7.3). Physical properties: oil.

[0337]

Example 55 Dithiocarbonate = S-isopropyl = ester
＝ O- [5,5-dimethyl-1-methoxymethoxy-
2-oxo-3- (2,4,6-trimethylphenyl)
-2,5-dihydro-1H-pyrrol-4-yl] S
Ter (Compound No. 1-130) ¹ H-NMR (CDCl_Three) δ (ppm): 6.80 (2H, s), 5.06 (2H, s),
3.61 (3H, s), 3.49 (1H, septet, J = 7.0), 2.22 (3H,
s), 2.16 (6H, s), 1.56 (6H, s), 1.22 (6H, d, J = 6.9
6). Physical properties: oil.

[0338]

Example 56 Dithiocarbonate = S-phenyl = ester =
O- [5,5-dimethyl-1-methoxymethoxy-2-
Oxo-3- (2,4,6-trimethylphenyl)-
2,5-Dihydro-1H-pyrrol-4-yl] ester (Compound No. 1-134) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.47-7.28 (5H, m), 6.84 (2H,
s), 5.04 (2H, s), 3.60 (3H, s), 2.28 (3H, s), 2.1
5 (6H, s), 1.49 (6H, s). Physical properties: oil.

[0339]

Example 57 5,5-Dimethyl-1-ethoxymethoxy-4-hydroxy-2-oxo-3- (2,4,6-
(Trimethylphenyl) -2,5-dihydro-1H-pyrrole (Compound No. 1-135) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.88 (2H, s), 5.02 (2H, s),
3.82 (2H, q, J = 7.0), 2.27 (3H, s), 2.11 (6H, s),
1.48 (6H, s), 1.28 (3H, t, J = 7.0). Physical properties: crystals (melting point: 152-156 ° C).

[0340]

Example 58 2,2-Dimethylpropionic acid = 5,5-dimethyl-1-ethoxymethoxy-2-oxo-3- (2,4,6-trimethylphenyl) -2,
5-dihydro-1H-pyrrol-4-yl ester (Compound No. 1-136) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.82 (2H, s), 5.11 (2H, s),
3.87 (2H, q, J = 7.0), 2.24 (3H, s), 2.15 (6H, s),
1.48 (6H, s), 1.29 (3H, t, J = 7.0), 1.08 (9H, s). Physical properties: crystals (melting point: 75-76 ° C).

[0341]

Example 59 3,3-Dimethylbutyric acid =
5,5-dimethyl-1-ethoxymethoxy-2-oxo-3- (2,4,6-trimethylphenyl) -2,5-
Dihydro-1H-pyrrol-4-yl ester (Compound No. 1-137) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.83 (2H, s), 5.12 (2H, s),
3.88 (2H, q, J = 7.0), 2.24 (3H, s), 2.20 (2H, s),
2.16 (6H, s), 1.51 (6H, s), 1.30 (3H, t, J = 7.0),
0.85 (9H, s). Physical properties: amorphous.

[0342]

EXAMPLE 60 Dithiocarbonate = S-ethyl = ester = O
-[5,5-dimethyl-1-ethoxymethoxy-2-oxo-3- (2,4,6-trimethylphenyl) -2,
5-Dihydro-1H-pyrrol-4-yl] ester (Compound No. 1-138) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.80 (2H, s), 5.11 (2H, s),
3.87 (2H, q, J = 7.0), 2.98 (2H, q, J = 7.5), 2.23 (3
H, s), 2.17 (6H, s), 1.56 (6H, s), 1.29 (3H, t, J =
7.0), 1.16 (3H, t, J = 7.5). Physical properties: oil.

[0343]

Example 61 5,5-Dimethyl-1-methoxyethoxy-4-hydroxy-2-oxo-3- (2,4,6-
(Trimethylphenyl) -2,5-dihydro-1H-pyrrole (Compound No. 1-139) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.88 (2H, s), 4.23-4.18 (2H,
m), 3.68-3.63 (2H, m), 3.39 (3H, s), 2.26 (3H,
s), 2.11 (6H, s), 1.49 (6H, s). Physical properties: Crystal (melting point: 137-139 ° C).

[0344]

Example 62 2,2-Dimethylpropionic acid = 5,5-dimethyl-1-methoxyethoxy-2-oxo-3- (2,4,6-trimethylphenyl) -2,
5-Dihydro-1H-pyrrol-4-yl ester (Compound No. 1-140) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.82 (2H, s), 4.28-4.32 (1H,
m), 3.69-3.73 (1H, m), 3.43 (3H, s), 2.24 (3H,
s), 2.15 (6H, s), 1.49 (6H, s), 1.07 (9H, s). Physical properties: oil.

[0345]

EXAMPLE 63 Dithiocarbonate = S-ethyl = ester = O
-[5,5-dimethyl-1-methoxyethoxy-2-oxo-3- (2,4,6-trimethylphenyl) -2,
5-Dihydro-1H-pyrrol-4-yl] ester (Compound No. 1-142) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.80 (2H, s), 4.32-4.28 (2H,
m), 3.73-3.69 (2H, m), 3.43 (3H, s), 2.97 (2H, q,
J = 7.5), 2.22 (3H, s), 2.16 (6H, s), 1.56 (6H, s),
1.16 (3H, t, J = 7.5). Physical properties: oil.

[0346]

Example 64 5,5-Dimethyl-1-methoxyethoxymethoxy-4-hydroxy-2-oxo-3- (2,5
4,6-trimethylphenyl) -2,5-dihydro-1
H-pyrrole (Compound No. 1-143) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.87 (2H, s), 5.06-5.05 (2H,
m), 3.95-3.91 (2H, m), 3.59-3.55 (2H, m), 3.36 (3
H, s), 2.26 (3H, s), 2.10 (6H, s), 1.47 (6H, s). Physical properties: oil.

[0347]

Example 65 2,2-Dimethylpropionic acid = 5,5-dimethyl-1-methoxyethoxymethoxy-2-oxo-3- (2,4,6-trimethylphenyl) -2,5-dihydro- 1H-pyrrol-4-yl =
Ester (Compound No. 1-144) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.82 (2H, s), 5.14 (2H, s),
4.02-3.98 (2H, m), 3.64-3.40 (2H, m), 3.40 (3H,
s), 2.24 (3H, s), 2.15 (6H, s), 1.49 (6H, s), 1.07
(9H, s). Physical properties: Crystal (melting point: 76-77 ° C).

[0348]

Example 66 Dithiocarbonate = S-ethyl = ester = O
-[5,5-Dimethyl-1-methoxyethoxymethoxy-2-oxo-3- (2,4,6-trimethylphenyl) -2,5-dihydro-1H-pyrrol-4-yl]
Ester (Compound No. 1-146) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.80 (2H, s), 5.14 (2H, s),
4.02-3.98 (2H, m), 3.64-3.60 (2H, m), 2.97 (2H, q,
J = 7.3), 2.22 (3H, s), 2.16 (6H, s), 1.56 (6H, s),
1.16 (3H, t, J = 7.3) ,. Physical properties: oil.

[0349]

Example 67 5,5-Dimethyl-1-methylthiomethoxy-4-hydroxy-2-oxo-3- (2,4,6
-Trimethylphenyl) -2,5-dihydro-1H-pyrrole (Compound No. 1-147) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.88 (2H, s), 5.12-5.10 (2H,
m), 2.32 (3Hs), 2.27 (3H, s), 2.10 (6H, s), 1.49
(6H, s). Physical properties: crystals (melting point: 139-141 ° C).

[0350]

Example 68 2,2-Dimethylpropionic acid = 5,5-dimethyl-1-methylthiomethoxy-2-
Oxo-3- (2,4,6-trimethylphenyl)-
2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 1-148) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.82 (2H, s), 5.19 (2H, s),
2.36 (3H, s), 2.27 (3H, s), 2.15 (6H, s), 1.51 (6
H, s), 1.09 (9H, s). Physical properties: oil.

[0351]

Example 69: S-ethyl dithiocarbonate = ester = O
-[5,5-dimethyl-1-methylthiomethoxy-2-
Oxo-3- (2,4,6-trimethylphenyl)-
2,5-Dihydro-1H-pyrrol-4-yl] ester (Compound No. 1-150) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.80 (2H, s), 5.19 (3H, s),
2.98 (2H, q, J = 7.5), 2.37 (3H, s), 2.23 (3H, s),
2.16 (6H, s), 1.55 (6H, s), 1.16 (3H, t, J = 7.5). Physical properties: oil.

[0352]

Example 70 5,5-Dimethyl-1- (2,2-dimethoxyethoxy) -4-hydroxy-2-oxo-3-
(2,4,6-trimethylphenyl) -2,5-dihydro-1H-pyrrole (Compound No. 1-151) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.89 (2H, s), 4.75 (1H , td,
J = 2.0, 5.1), 4.07 (2H, dd, J = 2.0, 5.1), 3.43 (6H,
d, J = 1.5), 2.26 (3H, s), 2.12 (6H, s), 1.50 (6H,
s). Physical properties: Crystal (melting point: 96-98 ° C).

[0353]

Example 71 2,2-Dimethylpropionic acid = 5,5-dimethyl-1- (2,2-dimethoxyethoxy) -2-oxo-3- (2,4,6-trimethylphenyl) -2 , 5-Dihydro-1H-pyrrol-4-yl ester (Compound No. 1-152) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.82 (2H, s), 4.78 (1H, t, J
= 5.1), 4.14 (2H, d, J = 5.1), 3.46 (6H, s), 2.24 (3
H, s), 2.15 (6H, s), 1.49 (6H, s), 1.07 (9H, s). Physical properties: crystals (melting point: 79-80 ° C).

[0354]

Example 72 Dithiocarbonate = S-ethyl = ester = O
-[5,5-Dimethyl-1- (2,2-dimethoxyethoxy) -2-oxo-3- (2,4,6-trimethylphenyl) -2,5-dihydro-1H-pyrrol-4-yl] Ester (Compound No. 1-154) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.80 (2H, s), 4.78 (1H, t, J
= 5.1), 4.14 (2H, d, J = 5.1), 3.46 (6H, s), 2.97 (2
H, q, J = 7.3), 2.22 (3H, s), 2.16 (6H, s), 1.56 (6
H, s), 1.16 (3H, t, J = 7.3). Physical properties: oil.

[0355]

Example 73 5,5-Dimethyl-1-([1,3] dioxolan-2-ylmethoxy) -4-hydroxy-2
-Oxo-3- (2,4,6-trimethylphenyl)-
2,5-dihydro-1H-pyrrole (Compound No. 1-1
55) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.84 (2H, s), 5.24 (1H, t, J
= 4.2), 4.06 (2H, d, J = 4.4), 4.07-3.81 (4H, m), 2.2
5 (3H, s), 2.07 (6H, s), 1.45 (6H, s). Physical properties: crystals (melting point: 147-151 ° C).

[0356]

Example 74 2,2-Dimethylpropionic acid = 5,5-dimethyl-1-([1,3] dioxolan-2-ylmethoxy) -2-oxo-3- (2,4,6
-Trimethylphenyl) -2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 1-156) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.81 (2H, s), 5.32 (1H , t, J
= 4.4), 4.18 (2H, d, J = 4.4), 4.03-3.92 (4H, m), 2.2
3 (3H, s), 2.15 (6H, s), 1.49 (6H, s), 1.08 (9H,
s). Physical properties: oil.

[0357]

Example 75 Dithiocarbonate = S-ethyl = ester = O
-[5,5-dimethyl-1-([1,3] dioxolan-2-ylmethoxy) -2-oxo-3- (2,4,6
-Trimethylphenyl) -2,5-dihydro-1H-pyrrol-4-yl] ester (Compound No. 1-158) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.80 (2H, s), 5.31 (1H , t, J
= 4.4), 4.18 (2H, d, J = 4.4), 4.06-3.89 (4H, m), 2.9
7 (2H, q, J = 7.3), 2.22 (3H, s), 2.16 (6H, s), 1.5
7 (6H, s), 1.16 (3H, t, J = 7.3). Physical properties: oil.

[0358]

Example 76 5,5-Dimethyl-1- (tetrahydrofuran-2-ylmethoxy) -4-hydroxy-2-oxo-3- (2,4,6-trimethylphenyl) -2,
5-Dihydro-1H-pyrrol-2-one (Compound No. 1-159) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.87 (2H, s), 4.30-4.11 (1H,
m), 4.10-3.98 (2H, m), 3.92-3.68 (2H, m), 2.26 (3
H, s), 2.11 (6H, s), 2.10-1.53 (4H, m), 1.47 (6H,
s). Physical properties: oil.

[0359]

Example 77 2,2-Dimethylpropionic acid = 5,5-dimethyl-1- (tetrahydrofuran-2
-Ylmethoxy) -2-oxo-3- (2,4,6-trimethylphenyl) -2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 1-160) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.81 (2H, s), 4.34-4.10 (3H,
m), 3.95-3.75 (2H, m), 2.24 (3H, s), 2.15 (6H,
s), 2.10-1.70 (4H, m), 1.49 (6H, d, J = 1.5), 1.07
(9H, s). Physical properties: oil.

[0360]

Example 78 2,2-Dimethylpropionic acid = 5,5-dimethyl-1- (pyridin-3-ylmethoxy) -2-oxo-3- (2,4,6-trimethylphenyl) -2, 5-dihydro-1H-pyrrol-4-yl ester (Compound No. 1-164) ¹ H-NMR (CDCl ₃ ) δ (ppm): 8.69 (1H, m), 8.62-8.61 (1H,
m), 7.92-7.87 (1H, m), 7.37-7.30 (1H, m), 6.83 (2
H, s), 5.19 (2H, s), 2.24 (3H, s), 2.15 (6H, s), 1.
32 (6H, s), 1.06 (9H, s). Physical properties: crystals (melting point: 122-124 ° C).

[0361]

Example 79 Dithiocarbonate = S-ethyl = ester = O
-[5,5-Dimethyl-1- (pyridin-3-ylmethoxy) -2-oxo-3- (2,4,6-trimethylphenyl) -2,5-dihydro-1H-pyrrol-4-yl] ester (Compound No. 1-166) ¹ H-NMR (CDCl ₃ ) δ (ppm): 8.67 (1H, m), 8.61-8.59 (1H,
m), 7.93-7.87 (1H, s), 7.37-7.30 (1H, m), 6.85 (2
H, s), 5.18 (2H, s), 2.96 (2H, q, J = 7.3), 2.25 (3
H, s), 2.16 (6H, s), 1.41 (6H, s), 1.15 (3H, t, J =
7.3). Physical properties: oil.

[0362]

Example 80 5,5-Dimethyl-1-cyanomethoxy-4-hydroxy-3- (2,4,6-trimethylphenyl) -2,5-dihydro-1H-pyrrol-2-one (Compound No. 1) -167) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.93 (2H, s), 4.85 (2H, s),
2.29 (3H, s), 2.14 (6H, s), 1.56 (6H, s). Physical properties: crystals (melting point: 158-163 ° C).

[0363]

Example 81 2,2-Dimethylpropionic acid = 5,5-dimethyl-1-cyanomethoxy-2-oxo-3- (2,4,6-trimethylphenyl) -2,5
-Dihydro-1H-pyrrol-4-yl ester (Compound No. 1-168) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.84 (2H, s), 4.90 (2H, s),
2.25 (3H, s), 2.15 (6H, s), 1.54 (6H, s), 1.08 (9
H, s). Physical properties: Crystal (melting point: 117-120 ° C).

[0364]

Example 82 5,5-Dimethyl-1-benzyloxymethoxy-4-hydroxy-2-oxo-3- (2,5
4,6-trimethylphenyl) -2,5-dihydro-1
H-pyrrole (Compound No. 1-171) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.39-7.33 (5H, m), 6.91 (2H,
s), 2.27 (3H, s), 6.40 (1H, brd.s), 5.14 (2H, s),
4.88 (2H, s), 2.27 (3H, s), 2.14 (6H, s), 1.52 (6
H, s). Physical properties: Crystal (melting point: 85-87 ° C).

[0365]

Example 83 2,2-Dimethylpropionic acid
Do = 5,5-dimethyl-1-benzyloxymethoxy-
2-oxo-3- (2,4,6-trimethylphenyl)
-2,5-dihydro-1H-pyrrol-4-yl = es
Ter (Compound No. 1-172) ¹ H-NMR (CDCl_Three) δ (ppm): 7.39-7.33 (5H, m), 6.83 (2H,
 s), 5.19 (2H, s), 4.90 (2H, s), 2.24 (3H, s), 2.1
6 (6H, s), 1.49 (6H, s), 1.07 (9H, s). Physical properties: oil.

[0366]

Example 84 5,5-Dimethyl-4-hydroxy-1
-(2,2,2-trifluoroethoxymethoxy) -2
-Oxo-3- (2,4,6-trimethylphenyl)-
2,5-dihydro-1H-pyrrole (Compound No. 1-1
79) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.88 (2H, s), 5.07 (2H, s),
4.19 (2H, q, J = 8.8), 2.26 (3H, s), 2.09 (6H, s),
1.46 (6H, s). Physical properties: crystals (melting point: 140-141 ° C).

[0367]

Example 85 2,2-Dimethylpropionic acid = 5,5-dimethyl-1- (3-chloroallyloxy) -2-oxo-3- (2,4,6-trimethylphenyl) -2, 5-Dihydro-1H-pyrrol-4-yl ester (Compound No. 1-192) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.82 (2H, s), 6.35-6.23 (2H
m), 4.62 (2H, dd, J = 0.7, 7.0), 2.24 (3H, s), 2.15
(6H, s), 1.49 (6H, s), 1.07 (9H, s). Physical properties: oil.

[0368]

Example 86 3,3-dimethylbutyric acid =
5,5-dimethyl-1-acetoxy-2-oxo-3-
(2,4,6-trimethylphenyl) -2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 1-216) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.83 (2H, s), 2.27 (3H, s),
2.24 (3H, s), 2.19 (2H, s), 2.17 (6H, s), 1.47 (6H,
s), 0.83 (6H, s). Physical properties: crystals (melting point: 117-118 ° C).

[0369]

Example 87 3,3-Dimethylbutyric acid =
5,5-dimethyl-1-pivaloyloxy-2-oxo-3- (2,4,6-trimethylphenyl) -2,5-
Dihydro-1H-pyrrol-4-yl ester (Compound No. 1-218) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.81 (2H, s), 2.23 (3H, s),
2.19 (2H, s), 2.18 (6H, s), 1.45 (6H, s), 1.38 (9
H, s), 0.83 (9H, s). Physical properties: Crystal (melting point: 95-97 ° C).

[0370]

Example 88 3,3-Dimethylbutenoic acid = 5,5-dimethyl-1-benzoyloxy-2-oxo-3- (2,4,6-trimethylphenyl) -2,5
-Dihydro-1H-pyrrol-4-yl ester (Compound No. 1-220) ¹ H-NMR (CDCl ₃ ) δ (ppm): 8.19-8.14 (2H, m), 7.65-7.46
(3H, m), 6.84 (2H, s), 2.24 (3H, s), 2.22 (6H,
s), 2.21 (2H, s), 1.55 (6H, s), 0.84 (9H, s). Physical properties: Crystal (melting point: 102-107 ° C).

[0371]

Example 89 3,3-Dimethylbutyric acid =
5,5-dimethyl-1- (3,3-dimethylbutenoyloxy) -2-oxo-3- (2,4,6-trimethylphenyl) -2,5-dihydro-1H-pyrrole-4-
Il = ester (Compound No. 1-222) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.82 (2H, s), 2.43 (2H, s),
2.23 (3H, s), 2.19 (2H, s), 2.18 (6H, s), 1.47 (6
H, s), 1.13 (9H, s), 0.83 (9H, s). Properties: Oil

[0372]

Example 90 3,3-Dimethylbutenoic acid = 5,5-dimethyl-1-dimethylaminocarbonyloxy-2-oxo-3- (2,4,6-trimethylphenyl) -2,5-dihydro -1H-pyrrol-4-yl ester (Compound No. 1-226) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.82 (2H, s), 3.08 (3H, brd.
s), 3.01 (3H, brd.s), 2.23 (3H, s), 2.18 (5H, s),
1.49 (6H, s), 0.83 (9H, s). Physical properties: Crystal (melting point: 160-163 ° C).

[0373]

Example 91 3,3-Dimethylbutyric acid =
5,5-dimethyl-1-methanesulfonyloxy-2-
Oxo-3- (2,4,6-trimethylphenyl)-
2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 1-228) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.85 (2H, s), 3.34 (3H, s),
2.24 (3H, s), 2.21 (2H, s), 2.15 (6H, s), 1.56 (6
H, s), 0.84 (9H, s). Physical properties: oil.

[0374]

Example 92 4-Hydroxy-1-methoxy-8-methyl-3- (2,4,6-trimethylphenyl) -1-
Azaspiro [4.5] decane-3-en-2-one (Compound No. 1-275) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.92 (2H, s), 5.74 (1H, brd.
s), 3.96 (3H, s), 2.28 (3H, s), 2.15 (6H, s), 2.30-
1.51 (9H, m), 0.97 (3H, d, J = 6.0). Physical properties: crystals (melting point: 186-188 ° C).

[0375]

Working Example 93 4-Hydroxy-1,8-dimethoxy-
3- (2,4,6-trimethylphenyl) -1-azaspiro [4,5] decane-3-en-2-one (Compound No. 1-279) ¹ H-NMR (DMSO-d ₆ ) δ (ppm) ): 11.30 (1H, s), 6.88 (2H,
s), 3.80 (3H, s), 3.44-3.30 (1H, m), 3.25 (3H, s),
2.24 (3H, s), 2.03 (6H, s), 2.02-1.70 (8H, m). Physical properties: crystals (melting point: 162-163 ° C).

[0376]

Example 94 5-Ethyl-5-methyl-1-methoxymethoxy-4-hydroxy-2-oxo-3- (2
4,6-trimethylphenyl) -2,5-dihydro-1
H-pyrrole (Compound No. 1-299) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.91 (2H, s), 5.01 (2H, d,
J = 2.9), 3.58 (3H, s), 2.28 (3H, s), 2.18 (3H, s),
2.14 (3H, s), 1.95-1.77 (2H, m), 1.51 (3H, s), 0.8
9 (3H, t, J = 7.3). Physical properties: crystals (melting point: 157-159 ° C).

[0377]

Example 95 5-isopropyl-5-methyl-1-methoxymethoxy-4-hydroxy-2-oxo-3-
(2,4,6-trimethylphenyl) -2,5-dihydro-1H-pyrrole (Compound No. 1-303) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.90 (2H, s), 5.02 (2H , s),
3.57 (3H, s), 2.27 (3H, s), 2.18 (3H, s), 2.12 (3
H, s), 2.35-2.15 (1H, m), 1.56 (3H, s), 1.13 (3H,
d, J = 7.0), 1.00 (3H, d, J = 7.0). Physical properties: amorphous.

[0378]

Example 96 5-Benzyl-5-methyl-1-methoxymethoxy-4-hydroxy-2-oxo-3- (2,
4,6-trimethylphenyl) -2,5-dihydro-1
H-pyrrole (Compound No. 1-311) ¹ H-NMR (DMSO-d ₆ ) δ (ppm): 11.39 (1H, s), 7.32-7.15
(5H, m), 6.77 (1H, s), 6.65 (1H, s), 5.04 (2H, ABq,
J = 7.3), 3.56 (3H, s), 3.08 (2H, ABq, J = 13.6), 2.1
6 (3H, s), 1.98 (3H, s), 1.54 (3H, s), 1.15 (3H,
s). Physical properties: amorphous.

[0379]

Example 97 5,5-Diethyl-1-methoxymethoxy-4-hydroxy-2-oxo-3- (2,4,6-
(Trimethylphenyl) -2,5-dihydro-1H-pyrrole (Compound No. 1-315) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.92 (2H, s), 5.01 (2H, s),
3.56 (3H, s), 2.28 (3H, s), 2.19 (6H, s), 1.95-1.
77 (4H, m), 0.91 (6H, t, J = 7.4). Physical properties: crystals (melting point: 147-149 ° C).

[0380]

Example 98 4-Hydroxy-8-methoxy-1-methoxymethoxy-3- (2,4,6-trimethylphenyl) -1-azaspiro [4,5] decane-3-en-2
-One (Compound No. 1-321) ¹ H-NMR (DMSO-d ₆ ) δ (ppm): 11.43 (1H, s), 6.87 (2H,
s), 4.98 (2H, s), 3.47 (3H, s), 3.35-3.18 (1H, m),
3.25 (3H, s), 2.24 (3H, s), 2.13-1.70 (14H, m). Physical properties: crystals (melting point: 164-165 ° C).

[0381]

Example 99 Cyclopropanecarboxylic acid 1-methoxymethoxy-2-oxo-1-azaspiro [4,5] decane-3-en-4-yl ester (Compound No. 1-389) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.84 (2H, s), 5.07 (2H, s),
3.62 (3H, s), 2.30-0.74 (24H, m). Physical properties: oil.

[0382]

Example 100 Cyclopropanecarboxylic acid = 5,5-dimethyl-1-methoxymethoxy-2-
Oxo-3- (2,4,6-trimethylphenyl)-
2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 1-390) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.84 (2H, s), 5.05 (2H, s),
3.61 (3H, s), 2.25 (3H, s), 2.15 (6H, s), 1.65-1.
56 (1H, m), 1.50 (6H, s), 1.08-0.80 (4H, m). Physical properties: amorphous.

[0383]

Example 101 1-Methylcyclopropanecarboxylic acid = 5,5-dimethyl-1-methoxymethoxy-2-oxo-3- (2,4,6-trimethylphenyl) -2,5-dihydro-1H- Pyrrole-4-yl ester (Compound No. 1-391) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.84 (2H, s), 5.05 (2H, s),
3.61 (3H, s), 2.26 (3H, s), 2.15 (6H, s), 1.48 (6
H, s), 1.24 (3H, s), 1.10-1.04 (2H, m), 0.75-0.65
(2H, m). Physical properties: amorphous.

[0384]

Example 102 2-Methylcyclopropanecarboxylic acid = 5,5-dimethyl-1-methoxymethoxy-2-oxo-3- (2,4,6-trimethylphenyl) -2,5-dihydro-1H- Pyrrole-4-yl ester (Compound No. 1-392) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.84 (2H, s), 5.05 (2H, s),
3.61 (3H, s), 2.25 (3H, s), 2.15 (6H, s), 1.75-1.
60 (1H, m), 1.50 (3H, s), 1.38-1.26 (1H, m), 1.14
0.97 (4H, m), 0.73-0.64 (1H, m). Physical properties: oil.

[0385]

Example 103 1-Methyl 2,2-dichlorocyclopropanecarboxylic acid = 5,5-dimethyl-
1-methoxymethoxy-2-oxo-3- (2,4,6
-Trimethylphenyl) -2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 1-393) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.84 (1H, s), 6.82 (1H , s),
5.06 (2H, s), 3.61 (3H, s), 2.24 (3H, s), 2.18 (3
H, s), 2.15 (3H, s), 1.54 (3H, s), 1.51 (3H, s), 1.
49-1.25 (5H, m). Physical properties: oil.

[0386]

Example 104 1-cyanocyclopropanecarboxylic acid = 5,5-dimethyl-1-methoxymethoxy-2-oxo-3- (2,4,6-trimethylphenyl) -2,5-dihydro-1H- Pyrrole-4-yl ester (Compound No. 1-394) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.86 (2H, s), 5.06 (2H, s),
3.62 (3H, s), 2.26 (3H, s), 2.17 (6H, s), 1.61-1.
30 (10H, m). Physical properties: Crystal (melting point: 60-62 ° C).

[0387]

Example 105 Cyclobutanecarboxylic acid = 5,5-dimethyl-1-methoxymethoxy-2-oxo-3- (2,4,6-trimethylphenyl) -2,
5-Dihydro-1H-pyrrol-4-yl ester (Compound No. 1-395) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.84 (2H, s), 5.05 (2H, s),
3.61 (3H, s), 3.23-3.10 (1H, m), 2.38-1.70 (15H,
m), 1.49 (6H, s). Physical properties: oil.

[0388]

Example 106 Cyclopentanecarboxylic acid = 5,5-dimethyl-1-methoxymethoxy-2-
Oxo-3- (2,4,6-trimethylphenyl)-
2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 1-396) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.83 (2H, s), 5.05 (2H, s),
3.61 (3H, s), 2.32-2.04 (1H, m), 2.24 (3H, s), 2.
15 (6H, s), 1.95-1.07 (17H, m). Physical properties: oil.

[0389]

Example 107 2-chloroacrylic acid =
5,5-dimethyl-1-methoxymethoxy-2-oxo-3- (2,4,6-trimethylphenyl) -2,5-
Dihydro-1H-pyrrol-4-yl ester (Compound No. 1-397) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.85 (2H, s), 6.53 (1H, br)
ds), 6.08 (1H, brd.s), 5.06 (2H, s), 3.62 (3H, s),
2.25 (3H, s), 2.17 (6H, s), 1.53 (6H, s). Physical properties: oil.

[0390]

Working Example 108 2-Chlorobenzoic Acid =
5,5-dimethyl-1-methoxymethoxy-2-oxo-3- (2,4,6-trimethylphenyl) -2,5-
Dihydro-1H-pyrrol-4-yl ester (Compound No. 1-398) ¹ H-NMR (CDCl ₃ ) δ (ppm): 8.01-7.96 (1H, m), 7.62-7.2
7 (3H, s), 6.83 (2H, s), 5.09 (2H, s), 3.63 (3H,
s), 2.23 (3H, s), 2.21 (6H, s). Physical properties: amorphous.

[0391]

Working Example 109 2-Methylbenzoic Acid =
5,5-dimethyl-1-methoxymethoxy-2-oxo-3- (2,4,6-trimethylphenyl) -2,5-
Dihydro-1H-pyrrol-4-yl ester (Compound No. 1-399) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.85-7.81 (1H, m), 7.43-7.3
8 (1H, m), 7.28-7.19 (2H, m), 6.80 (2H, s), 5.08
(2H, s), 3.63 (3H, s), 2.34 (3H, s), 2.20 (6H, s),
1.58 (6H, s). Physical properties: oil.

[0392]

Example 110 2-methoxybenzoic acid =
5,5-dimethyl-1-methoxymethoxy-2-oxo-3- (2,4,6-trimethylphenyl) -2,5-
Dihydro-1H-pyrrol-4-yl ester (Compound No. 1-400) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.70-7.64 (1H, m), 7.55-7.4
5 (1H, m), 6.81 (2H, s), 5.08 (2H, s), 3.84 (3H,
s), 3.62 (3H, s), 2.22 (6H, s), 2.21 (3H, s), 1.56
(6H, s). Physical properties: crystals (melting point: 101-102 ° C).

[0393]

Example 111 3-methoxybenzoic acid =
5,5-dimethyl-1-methoxymethoxy-2-oxo-3- (2,4,6-trimethylphenyl) -2,5-
Dihydro-1H-pyrrol-4-yl ester (Compound No. 1-401) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.57 (1H, d, J = 7.6), 7.44-
7.32 (1H, m), 7.35 (1H, t, J = 7.8), 7.15-7.12 (1H,
m), 6.80 (2H, s), 5.08 (2H, s), 3.81 (3H, s), 3.62
(3H, s), 2.21 (6H, s), 2.19 (3H, s), 1.57 (6H,
s). Physical properties: crystals (melting point: 102-104 ° C).

[0394]

Example 112 4-methoxybenzoic acid =
5,5-dimethyl-1-methoxymethoxy-2-oxo-3- (2,4,6-trimethylphenyl) -2,5-
Dihydro-1H-pyrrol-4-yl ester (Compound No. 1-402) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.91 (2H, d, J = 8.8), 6.89
(2H, d, J = 8.8), 6.79 (2H, s), 5.08 (2H, s), 3.85
(6H, s), 3.62 (3H, s), 2.21 (6H, s), 2.19 (3H, s),
1.57 (6H, s). Physical properties: oil.

[0395]

Example 113 2-trifluoromethylbenzoic acid = 5,5-dimethyl-1-methoxymethoxy-
2-oxo-3- (2,4,6-trimethylphenyl)
-2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 1-403) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.75-7.52 (4H, m), 6.86 (2
H, s), 5.08 (2H, s), 3.63 (3H, s), 2.25 (3H, s),
2.19 (6H, s), 1.57 (6H, s). Physical properties: crystals (melting point: 116-117 ° C).

[0396]

Example 114 2,6-Dimethylbenzoic acid = 5,5-dimethyl-1-methoxymethoxy-2-oxo-3- (2,4,6-trimethylphenyl) -2,
5-Dihydro-1H-pyrrol-4-yl ester (Compound No. 1-404) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.36 (1H, t, J = 9.0), 6.92
(2H, s), 6.62 (2H, d, J = 9.0), 5.03 (2H, s), 3.90
(6H, s), 3.60 (3H, s), 2.28 (3H, s), 2.15 (6H, s),
1.53 (6H, s). Physical properties: crystals (melting point: 141-145 ° C).

[0397]

Example 115 3-Methyl-2-methoxybenzoic acid
Quasid = 5,5-dimethyl-1-methoxymethoxy
-2-oxo-3- (2,4,6-trimethylphenyi
) -2,5-dihydro-1H-pyrrol-4-yl =
Ester (Compound No. 1-405) ¹ H-NMR (CDCl_Three) δ (ppm): 7.56 (1H, d, J = 7.8), 7.37
(1H, d, J = 7.2), 7.03 (1H, dd, J = 7.8, 7.2), 6.79 (2
H, s), 5.08 (2H, s), 3.63 (3H, s), 3.39 (3H, s), 2.
26 (3H, s), 2.22 (6H, s), 2.18 (3H, s), 1.58 (6H,
s). Physical properties: crystals (melting point: 177-180 ° C).

[0398]

Example 116 4-Methyl-2-methoxybenzoic acid
Quasid = 5,5-dimethyl-1-methoxymethoxy
-2-oxo-3- (2,4,6-trimethylphenyi
) -2,5-dihydro-1H-pyrrol-4-yl =
Ester (Compound No. 1-406) ¹ H-NMR (CDCl_Three) δ (ppm): 7.61 (1H, d, J = 7.8), 6.80
(2H, s), 6.77-6.74 (1H, m), 5.07 (2H, s), 3.82 (3H,
 s), 3.62 (3H, s), 2.37 (3H, s), 2.22 (6H, s), 2.2
0 (3H, s), 1.55 (6H, s). Physical properties: Crystal (melting point: 115-118 ° C).

[0399]

Example 117 3,4,5-Trimethoxybenzoic acid
Quasid = 5,5-dimethyl-1-methoxymethoxy
-2-oxo-3- (2,4,6-trimethylphenyi
) -2,5-dihydro-1H-pyrrol-4-yl =
Ester (Compound No. 1-407) ¹ H-NMR (CDCl_Three) δ (ppm): 7.18 (2H, s), 6.81 (2H, s),
 5.08 (2H, s), 3.90 (3H, s), 3.87 (6H, s), 3.63 (3
H, s), 2.22 (6H, s), 2.20 (3H, s), 1.58 (6H, s). Physical properties: crystals (melting point: 159-160 ° C).

[0400]

Example 118 5-Methylchroman-6-carboxylic acid = 5,5-dimethyl-1-methoxymethoxy-2-oxo-3- (2,4,6-trimethylphenyl) -2,5-dihydro- 1H-pyrrol-4-yl ester (Compound No. 1-408) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.63 (1H, d, J = 8.8), 6.79
(1H, s), 6.67 (1H, d, J = 8.8), 5.08 (2H, s), 4.18-
4.08 (2H, m), 3.62 (3H, s), 2.66-2.60 (2H, m), 2.20
(9H, s), 2.07-1.97 (2H, s), 1.56 (6H, s). Physical properties: crystals (melting point: 108-109 ° C).

[0401]

Working Example 119 Benzo [1,3] dioxol-5
Carboxylic acid = 5,5-dimethyl-1-methoxymethoxy-2-oxo-3- (2,4,6-trimethylphenyl) -2,5-dihydro-1H-pyrrol-4-yl = ester (compound number 1-409) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.57 (1H, dd, J = 8.5, 1.5),
7.34 (1H, d, J = 1.5), 6.82-6.80 (1H, m), 6.79 (2H,
s), 6.03 (2H, s), 5.07 (2H, s), 3.62 (3H, s), 2.20
(6H, s), 2.19 (3H, s), 1.56 (6H, s). Physical properties: amorphous.

[0402]

Example 120 Cyclopropylcarboxylic acid = 1-ethoxymethoxy-5,5-dimethyl-2-
Oxo-3- (2,4,6-trimethylphenyl)-
2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 1-410) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.84 (2H, s), 5.10 (2H, s),
3.87 (2H, q, J = 7.0), 2.25 (3H, s), 2.15 (6H, s),
1.64-1.55 (1H, m), 1.50 (6H, s), 1.29 (3H, t, J = 7.
0), 1.14-0.80 (4H, m). Physical properties: oil.

[0403]

Example 121 1-Methylcyclopropylcarboxylic acid = 1-ethoxymethoxy-5,5-dimethyl-2-oxo-3- (2,4,6-trimethylphenyl) -2,5-dihydro-1H- Pyrrole-4-yl ester (Compound No. 1-411) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.84 (2H, s), 5.10 (2H, s),
3.86 (2H, q, J = 7.0), 2.25 (3H, s), 2.14 (6H, s),
1.48 (6H, s), 1.28 (3H, s), 1.39-1.24 (2H, m), 1.1
7-0.96 (2H, m). Physical properties: amorphous.

[0404]

Example 122 1-cyanocyclopropylcarboxylic acid = 1-ethoxymethoxy-5,5-dimethyl-2-oxo-3- (2,4,6-trimethylphenyl) -2,5-dihydro-1H- Pyrrole-4-yl ester (Compound No. 1-412) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.86 (2H, s), 5.11 (2H, s),
3.87 (2H, q, J = 7.3), 2.26 (3H, s), 2.16 (6H, s),
1.62-1.18 (13H, m). Physical properties: oil.

[0405]

Working Example 123 1- (4-ethoxyphenyl) -2,
2-dichlorocyclopropylcarboxylic acid = 1-ethoxymethoxy-5,5-dimethyl-2-oxo-3- (2,4,6-trimethylphenyl) -2,5
-Dihydro-1H-pyrrol-4-yl ester (Compound No. 1-413) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.24-7.18 (2H, m), 6.88-6.8
0 (2H, m), 6.76 (1H, brd.s), 6.59 (1H, brd.s), 5.0
7 (2H, s), 4.06 (2H, q, J = 7.0), 3.83 (2H, q, J = 7.
0), 2.45 (1H, d, J = 7.7), 2.20 (3H, s), 2.16 (3H,
s), 1.98 (1H, d, J = 7.7), 1.74 (3H, s), 1.45 (3H,
t, J = 7.0), 1.41 (3H, s), 1.38 (3H, s), 1.26 (3H,
t, J = 7.0). Physical properties: oil.

[0406]

Example 124 Cyclobutylcarboxylic acid = 1-ethoxymethoxy-5,5-dimethyl-2-oxo-3- (2,4,6-trimethylphenyl) -2,
5-dihydro-1H-pyrrol-4-yl ester (Compound No. 1-414) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.83 (2H, s), 5.10 (2H, s),
3.86 (2H, q, J = 7.0), 3.23-3.09 (1H, m), 2.38-1.37
(21H, m), 1.28 (3H, t, J = 7.0). Physical properties: oil.

[0407]

Example 125 2-Chloroacrylic acid = 1
-Ethoxymethoxy-5,5-dimethyl-2-oxo-
3- (2,4,6-trimethylphenyl) -2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 1-415) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.84 ( 2H, s), 6.52 (1H, d,
J = 1.5), 6.08 (1H, d, J = 1.5), 5.11 (2H, s), 3.87 (2
H, q, J = 7.0), 2.24 (3H, s), 2.17 (6H, s), 1.53 (6
H, s), 1.29 (3H, t, J = 7.0). Physical properties: oil.

[0408]

Working Example 126 2-Methylbenzoic Acid = 1
-Ethoxymethoxy-5,5-dimethyl-2-oxo-
3- (2,4,6-trimethylphenyl) -2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 1-416) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.85- 7.81 (1H, m), 7.47-7.3
8 (1H, m), 7.27-7.19 (2H, m), 6.80 (2H, s), 5.14
(2H, s), 3.89 (2H, q, J = 7.0), 2.34 (3H, s), 2.20
(6H, s), 1.58 (6H, s), 1.30 (3H, t, J = 7.0). Physical properties: oil.

[0409]

Working Example 127 2-methoxybenzoic acid =
1-ethoxymethoxy-5,5-dimethyl-2-oxo-3- (2,4,6-trimethylphenyl) -2,5-
Dihydro-1H-pyrrol-4-yl ester (Compound No. 1-417) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.69-7.65 (1H, m), 7.54-7.4
5 (1H, m), 6.99-6.93 (2H, m), 6.81 (2H, s), 5.13
(2H, s), 3.88 (2H, q, J = 7.0), 3.84 (3H, s), 2.22
(9H, s), 1.56 (6H, s), 1.29 (3H, t, J = 7.3). Physical properties: Crystal (melting point: 62-64 ° C).

[0410]

Working Example 128 2-Chlorobenzoic Acid = 1
-Ethoxymethoxy-5,5-dimethyl-2-oxo-
3- (2,4,6-trimethylphenyl) -2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 1-418) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.61- 7.57 (1H, m), 7.46-7.4
3 (2H, m), 7.33-7.27 (1H, m), 6.83 (2H, s), 5.14
(2H, s), 3.88 (2H, q, J = 7.0), 2.22 (3H, s), 2.21
(6H, s), 1.58 (6H, s), 1.30 (3H, t, J = 7.0). Physical properties: oil.

[0411]

Working Example 129 3-Methoxybenzoic acid =
1-ethoxymethoxy-5,5-dimethyl-2-oxo-3- (2,4,6-trimethylphenyl) -2,5-
Dihydro-1H-pyrrol-4-yl ester (Compound No. 1-419) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.60-7.55 (1H, m), 7.45-7.4
3 (1H, m), 7.35 (1H, t, J = 8.0), 7.16-7.10 (1H, m),
6.80 (2H, s), 5.13 (2H, s), 3.88 (2H, q, J = 7.0),
3.82 (3H, s), 2.21 (6H, s), 2.19 (3H, s), 1.57 (6
H, s), 1.30 (3H, t, J = 7.0). Physical properties: oil.

[0412]

Example 130 2-Methylthiobenzoic acid = 1-ethoxymethoxy-5,5-dimethyl-2-oxo-3- (2,4,6-trimethylphenyl) -2,5
-Dihydro-1H-pyrrol-4-yl ester (Compound No. 1-420) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.90 (1H, dd, J = 8.0, 1.5),
7.56-7.45 (1H, m), 7.25-7.10 (2H, m), 6.80 (2H,
s), 5.13 (2H, s), 3.88 (2H, q, J = 7.0), 2.39 (3H,
s), 2.22 (6H, s), 2.19 (3H, s), 1.58 (6H, s), 1.29
(3H, t, J = 7.0). Physical properties: Crystal (melting point: 95-99 ° C).

[0413]

Working Example 131 3-Methylbenzoic Acid = 1
-Ethoxymethoxy-5,5-dimethyl-2-oxo-
3- (2,4,6-trimethylphenyl) -2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 1-421) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.79- 7.75 (2H, m), 7.43-7.2
8 (2H, m), 6.79 (2H, s), 5.13 (2H, s), 3.88 (2H,
q, J = 7.0), 2.38 (3H, s), 2.21 (6H, s), 2.19 (3H,
s), 1.57 (6H, s), 1.30 (3H, t, J = 7.0). Physical properties: oil.

[0414]

Example 132 3-trifluoromethylbenzoic acid = 1-ethoxymethoxy-5,5-dimethyl-
2-oxo-3- (2,4,6-trimethylphenyl)
-2,5-Dihydro-1H-pyrrol-4-yl ester (Compound No. 1-422) ¹ H-NMR (CDCl ₃ ) δ (ppm): 8.19-8.12 (2H, m), 7.88-7.8
4 (1H, m), 7.64-7.56 (1H, m), 6.80 (2H, s), 5.14
(2H, s), 3.89 (2H, q, J = 7.0), 2.21 (6H, s), 2.19
(3H, s), 1.59 (6H, s), 1.30 (3H, t, J = 7.0). Physical properties: oil.

[0415]

Working Example 133 3-Cyanobenzoic acid = 1
-Ethoxymethoxy-5,5-dimethyl-2-oxo-
3- (2,4,6-trimethylphenyl) -2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 1-423) ¹ H-NMR (CDCl ₃ ) δ (ppm): 8.23- 8.14 (2H, m), 7.88 (1
H, dt, J = 7.7, 1.5), 7.60 (1H, dd, J = 8.4, 7.7), 6.8
1 (2H, s), 5.14 (2H, s), 3.89 (2H, q, J = 7.0), 2.20
(9H, s), 1.58 (6H, s), 1.30 (3H, t, J = 7.0). Physical properties: crystals (melting point: 124-125 ° C).

[0416]

Working Example 134 3-Chlorobenzoic Acid = 1
-Ethoxymethoxy-5,5-dimethyl-2-oxo-
3- (2,4,6-trimethylphenyl) -2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 1-424) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.92 ( 1H, t, J = 1.8), 7.84
(1H, dt, J = 7.7, 1.5), 7.60-7.55 (1H, m), 7.39 (1H,
t, J = 7.7), 6.80 (2H, s), 5.13 (2H, s), 3.88 (2H,
q, J = 7.0), 2.20 (9H, s), 1.57 (6H, s), 1.30 (3H,
t, J = 7.0). Physical properties: oil.

[0417]

Working Example 135 4-Methoxybenzoic Acid =
1-ethoxymethoxy-5,5-dimethyl-2-oxo-3- (2,4,6-trimethylphenyl) -2,5-
Dihydro-1H-pyrrol-4-yl ester (Compound No. 1-425) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.94-7.89 (2H, m), 6.92-6.8
8 (2H, m), 6.79 (2H, s), 5.13 (2H, s), 3.88 (2H,
q, J = 7.0), 3.86 (3H, s), 2.21 (6H, s), 2.19 (3H,
s), 1.57 (6H, s), 1.29 (3H, t, J = 7.0). Physical properties: oil.

[0418]

Working Example 136 4-Methylbenzoic acid = 1
-Ethoxymethoxy-5,5-dimethyl-2-oxo-
3- (2,4,6-trimethylphenyl) -2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 1-426) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.85 ( 2H, d, J = 8.4), 7.23
(2H, d, J = 8.4), 6.78 (2H, s), 5.13 (2H, s), 3.88
(2H, q, J = 7.0), 2.40 (3H, s), 2.21 (6H, s), 2.18
(3H, s), 1.57 (6H, s), 1.29 (3H, t, J = 7.0). Physical properties: oil.

[0419]

Working Example 137 4-Chlorobenzoic acid = 1
-Ethoxymethoxy-5,5-dimethyl-2-oxo-
3- (2,4,6-trimethylphenyl) -2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 1-427) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.91- 7.85 (2H, m), 7.45-7.3
9 (2H, m), 6.79 (2H, s), 5.13 (2H, s), 3.88 (2H,
q, J = 7.0), 2.20 (9H, s), 1.57 (6H, s), 1.29 (3H,
t, J = 7.0). Physical properties: oil.

[0420]

Working Example 138 2-trifluoromethylbenzoic acid = 1-ethoxymethoxy-5,5-dimethyl-
2-oxo-3- (2,4,6-trimethylphenyl)
-2,5-Dihydro-1H-pyrrol-4-yl ester (Compound No. 1-428) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.76-7.51 (3H, m), 7.26-7.2
4 (1H, m), 6.86 (2H, s), 5.14 (2H, s), 3.89 (2H, q,
J = 7.0), 2.53 (3H, s), 2.19 (6H, s), 1.59 (6H, s),
1.30 (3H, t, J = 7.0). Physical properties: crystals (melting point: 105-107 ° C).

[0421]

Working Example 139 2-Phenoxybenzoic acid = 1-ethoxymethoxy-5,5-dimethyl-2-oxo-3- (2,4,6-trimethylphenyl) -2,5
-Dihydro-1H-pyrrol-4-yl ester (Compound No. 1-429) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.73 (1H, dd, J = 7.7, 1.8),
7.47 (1H, dt, J = 1.8, 7.7), 7.37-7.27 (2H, m), 7.16
-7.08 (2H, m), 6.92-6.88 (3H, m), 6.78 (2H, s), 5.0
9 (2H, s), 3.85 (2H, q, J = 7.0), 2.21 (3H, s), 2.15
(6H, s), 1.57 (6H, s), 1.27 (3H, t, J = 7.0). Physical properties: oil.

[0422]

Example 140 2-ethoxybenzoic acid =
1-ethoxymethoxy-5,5-dimethyl-2-oxo-3- (2,4,6-trimethylphenyl) -2,5-
Dihydro-1H-pyrrol-4-yl ester (Compound No. 1-430) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.61 (1H, dd, J = 8.0, 1.8),
7.46 (1H, dt, J = 1.8, 8.0), 7.00-6.88 (2H, m), 6.81
(2H, s), 5.13 (2H, s), 4.06 (2H, q, J = 7.0), 3.88
(2H, q, J = 7.0), 2.21 (9H, s), 1.57 (6H, s), 1.38
(3H, t, J = 7.0), 1.29 (3H, t, J = 7.0). Physical properties: Crystal (melting point: 90-91 ° C).

[0423]

Example 141 2-Propyloxybenzoic acid = 1-ethoxymethoxy-5,5-dimethyl-2-
Oxo-3- (2,4,6-trimethylphenyl)-
2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 1-431) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.62 (1H, dd, J = 8.0, 1.8),
7.46 (1H, dt, J = 1.8, 8.0), 6.95-6.80 (2H, m), 5.13
(2H, s), 3.92 (2H, q, J = 7.0), 3.88 (2H, q, J = 7.3),
2.21 (9H, s), 1.85-1.68 (2H, m), 1.57 (6H, s), 1.
29 (3H, t, J = 7.0), 0.98 (3H, t, J = 7.0). Physical properties: oil.

[0424]

Example 142 Nicotinic acid = 1-ethoxymethoxy-5,5-dimethyl-2-oxo-3- (2
4,6-trimethylphenyl) -2,5-dihydro-1
H-pyrrol-4-yl ester (Compound No. 1-4
32) ¹ H-NMR (CDCl ₃ ) δ (ppm): 9.14 (1H, d, J = 2.2), 8.79-
8.76 (1H, m), 8.20 (1H, dt, J = 8.0, 2.2), 7.43-7.36
(1H, m), 6.80 (2H, s), 5.14 (2H, s), 3.89 (2H, q,
J = 7.0), 2.21 (6H, s), 2.19 (3H, s), 1.59 (6H, s),
1.30 (3H, t, J = 7.0). Physical properties: oil.

[0425]

Working Example 143 4-trifluoromethylnicotinic acid = 1-ethoxymethoxy-5,5-dimethyl-
2-oxo-3- (2,4,6-trimethylphenyl)
-2,5-Dihydro-1H-pyrrol-4-yl ester (Compound No. 1-433) ¹ H-NMR (CDCl ₃ ) δ (ppm): 8.93 (1H, d, J = 5.1), 8.64
(1H, s), 7.64 (1H, d, J = 5.1), 6.86 (2H, s), 5.14
(2H, s), 3.89 (2H, q, J = 7.0), 2.25 (3H, s), 2.19
(6H, s), 1.58 (6H, s), 1.30 (3H, t, J = 7.0). Physical properties: oil.

[0426]

Example 144 2-methylthio-4-trifluoromethylpyrimidine-5-carboxylic acid = 1-
Ethoxymethoxy-5,5-dimethyl-2-oxo-3
-(2,4,6-trimethylphenyl) -2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 1-434) ¹ H-NMR (CDCl ₃ ) δ (ppm): 8.62 (1H , s), 6.84 (2H, s),
5.13 (2H, s), 3.88 (2H, q, J = 7.0), 2.62 (3H, s),
2.24 (3H, s), 2.17 (6H, s), 1.56 (6H, s), 1.30 (3
H, t, J = 7.0). Physical properties: crystals (melting point: 112-113 ° C).

[0427]

Example 145 5-Chloro-1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxylic acid-1-ethoxymethoxy-5,5-dimethyl-2-oxo-3- (2,4 , 6-Trimethylphenyl) -2,5-dihydro-1H-pyrrol-4-yl =
Ester (Compound No. 1-435) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.81 (2H, s), 5.12 (2H, s),
3.90 (3H, s), 3.88 (2H, q, J = 7.0), 2.22 (3H, s),
2.17 (6H, s), 1.54 (6H, s), 1.29 (3H, t, J = 7.0). Physical properties: amorphous.

[0428]

Example 146 4-Methyl- [1,2,3] thiadiazole-5-carboxylic acid = 1-ethoxymethoxy-5,5-dimethyl-2-oxo-3- (2
4,6-trimethylphenyl) -2,5-dihydro-1
H-pyrrol-4-yl ester (Compound No. 1-4
36) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.81 (2H, s), 5.12 (2H, s),
3.88 (2H, q, J = 7.0), 2.82 (3H, s), 2.21 (3H, s),
2.17 (6H, s), 1.56 (6H, s), 1.30 (3H, t, J = 7.0). Physical properties: crystals (melting point: 154-158 ° C).

[0429]

Working Example 147-Dimethylcarbamic acid = 1-
Ethoxymethoxy-5,5-dimethyl-2-oxo-3
-(2,4,6-trimethylphenyl) -2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 1-437) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.84 (2H , s), 5.10 (2H, s),
3.87 (2H, q, J = 7.0), 2.91 (3H, s), 2.74 (3H, s),
2.25 (3H, s), 2.17 (6H, s), 1.52 (6H, s), 1.28 (3
H, t, J = 7.0). Physical properties: Crystal (melting point: 92-93 ° C).

[0430]

Example 148 Morpholine-4-carboxylic acid = 1-ethoxymethoxy-5,5-dimethyl-2
-Oxo-3- (2,4,6-trimethylphenyl)-
2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 1-438) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.85 (2H, s), 5.10 (2H, s),
3.87 (2H, q, J = 7.0), 3.55-3.20 (8H, m), 2.26 (3H,
s), 2.16 (6H, s), 1.52 (6H, s), 1.29 (3H, t, J = 7.
0). Physical properties: Crystal (melting point: 88-89 ° C).

[0431]

Example 149 5,5-Dimethyl-1-ethoxymethoxy-4- (4-methoxybenzyloxy) -2-oxo-3- (2,4,6-trimethylphenyl) -2,5
-Dihydro-1H-pyrrole (Compound No. 1-439) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.00-6.79 (6H, m), 5.06 (2
H, s), 4.60 (2H, s), 3.85 (2H, q, J = 7.0), 3.79 (3
H, s), 2.28 (3H, s), 2.12 (6H, s), 1.47 (6H, s),
1.27 (3H, t, J = 7.0). Physical properties: oil.

[0432]

Example 150 Cyclopropylcarboxylic acid = 5,5-dimethyl-1-methoxyethoxy-2-
Oxo-3- (2,4,6-trimethylphenyl)-
2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 1-440) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.84 (2H, s), 4.32-4.26 (2
H, m), 3.73-3.68 (2H, m), 3.43 (3H, s), 2.25 (3H,
s), 2.15 (6H, s), 1.65-1.39 (7H, m), 0.89-0.79 (4
H, m). Physical properties: amorphous.

[0433]

Example 151 1-Methylcyclopropylcarboxylic acid = 5,5-dimethyl-1-methoxyethoxy-2-oxo-3- (2,4,6-trimethylphenyl) -2,5-dihydro-1H- Pyrrole-4-yl ester (Compound No. 1-441) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.84 (2H, s), 4.32-4.26 (2
H, m), 3.73-3.68 (2H, m), 3.43 (3H, s), 2.25 (3H,
s), 2.14 (6H, s), 1.49 (6H, s), 1.23 (3H, s), 1.10-
1.03 (2H, m), 0.77-0.64 (2H, m). Physical properties: amorphous.

[0434]

Example 152 1-cyanocyclopropylcarboxylic acid = 5,5-dimethyl-1-methoxyethoxy-2-oxo-3- (2,4,6-trimethylphenyl) -2,5-dihydro-1H- Pyrrole-4-yl ester (Compound No. 1-442) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.86 (2H, s), 4.33-4.10 (2
H, m), 3.73-3.68 (2H, m), 3.43 (3H, s), 2.26 (3H,
s), 2.16 (6H, s), 1.60-1.30 (10H, m). Physical properties: oil.

[0435]

Example 153 Cyclobutylcarboxylic acid = 5,5-dimethyl-1-methoxyethoxy-2-oxo-3- (2,4,6-trimethylphenyl) -2,
5-dihydro-1H-pyrrol-4-yl ester (Compound No. 1-443) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.83 (2H, s), 4.32-4.27 (2
H, m), 3.74-3.68 (2H, m), 3.43 (3H, s), 3.22-3.09
(1H, m), 2.38-1.76 (15H, m), 1.49 (6H, s). Physical properties: oil.

[0436]

Example 154 2-chloroacrylic acid =
5,5-dimethyl-1-methoxyethoxy-2-oxo-3- (2,4,6-trimethylphenyl) -2,5-
Dihydro-1H-pyrrol-4-yl ester (Compound No. 1-444) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.84 (2H, s), 6.52 (1H, d,
J = 1.8), 6.07 (1H, d, J = 1.8), 4.34-4.29 (2H, m), 3.
74-3.68 (2H, m), 3.43 (3H, s), 2.24 (3H, s), 2.17
(6H, s), 1.54 (6H, s). Physical properties: amorphous.

[0437]

Example 155 2-Methylbenzoic acid =
5,5-dimethyl-1-methoxyethoxy-2-oxo-3- (2,4,6-trimethylphenyl) -2,5-
Dihydro-1H-pyrrol-4-yl ester (Compound No. 1-445) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.84-7.79 (1H, m), 7.43-7.3
8 (1H, m), 7.27-7.19 (2H, m), 6.80 (2H, s), 4.36-
4.30 (2H, m), 3.76-3.70 (2H, m), 3.44 (3H, s), 2.3
4 (3H, s), 2.20 (6H, s), 1.58 (6H, s). Physical properties: oil.

[0438]

Example 156 2-Methylthiobenzoic acid = 5,5-dimethyl-1-methoxyethoxy-2-oxo-3- (2,4,6-trimethylphenyl) -2,5
-Dihydro-1H-pyrrol-4-yl ester (Compound No. 1-446) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.92-7.88 (1H, m), 7.49-7.4
6 (1H, m), 7.26-7.11 (2H, m), 6.80 (2H, s), 4.33 (2
H, t, J = 4.6), 3.81 (2H, t, J = 4.6), 3.44 (3H, s), 2.
41 (3H, s), 2.23 (6H, s), 2.20 (3H, s), 1.59 (6H,
s). Physical properties: crystals (melting point: 112-115 ° C).

[0439]

Example 157 2-methoxybenzoic acid =
5,5-dimethyl-1-methoxyethoxy-2-oxo-3- (2,4,6-trimethylphenyl) -2,5-
Dihydro-1H-pyrrol-4-yl ester (Compound No. 1-447) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.66 (1H, dd, J = 8.1, 1.8),
7.50 (1H, td, J = 8.1, 1.8), 6.98-6.91 (2H, m), 6.81
(2H, s), 4.32 (2H, t, J = 4.6), 3.84 (3H, s), 3.73
(2H, t, J = 4.6), 3.44 (3H, s), 2.22 (9H, s), 1.59
(6H, s). Physical properties: oil.

[0440]

Working Example 158 2-Bromobenzoic acid =
5,5-dimethyl-1-methoxyethoxy-2-oxo-3- (2,4,6-trimethylphenyl) -2,5-
Dihydro-1H-pyrrol-4-yl ester (Compound No. 1-448) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.66-7.62 (1H, m), 7.52-7.4
8 (1H, m), 7.36-7.31 (2H, m), 6.84 (2H, s), 4.36-
4.31 (2H, m), 3.76-3.71 (2H, m), 3.44 (3H, s), 2.2
3 (3H, s), 2.21 (6H, s), 1.60 (6H, s). Physical properties: Crystal (melting point: 60-63 ° C).

[0441]

Example 159 2-Nitrobenzoic acid =
5,5-dimethyl-1-methoxyethoxy-2-oxo-3- (2,4,6-trimethylphenyl) -2,5-
Dihydro-1H-pyrrol-4-yl ester (Compound No. 1-449) ¹ H-NMR (CDCl ₃ ) δ (ppm): 8.03-7.99 (1H, m), 7.82-7.6
0 (2H, m), 7.03-6.99 (1H, m), 6.88 (2H, s), 4.36-
4.31 (2H, m), 3.75-3.71 (2H, m), 3.44 (3H, s), 2.7
0 (3H, s), 2.17 (6H, s), 1.61 (6H, s). Physical properties: oil.

[0442]

Example 160 2-trifluoromethylbenzoic acid = 5,5-dimethyl-1-methoxyethoxy-
2-oxo-3- (2,4,6-trimethylphenyl)
-2,5-Dihydro-1H-pyrrol-4-yl ester (Compound No. 1-450) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.75-7.51 (3H, m), 7.26-7.2
4 (1H, m), 6.85 (2H, s), 4.36-4.31 (2H, m), 3.75-
3.71 (2H, m), 3.44 (3H, s), 2.25 (3H, s), 2.19 (6
H, s), 1.58 (6H, s). Physical properties: oil.

[0443]

Working Example 161 2-Methylsulfinylbenzoic acid = 5,5-dimethyl-1-methoxyethoxy-
2-oxo-3- (2,4,6-trimethylphenyl)
-2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 1-451) ¹ H-NMR (CDCl ₃ ) δ (ppm): 8.26 (1H, dd, J = 8.1, 1.1),
8.09 (1H, dd, J = 8.1, 1.1), 7.87 (1H, td, J = 7.3, 1.
5), 7.60 (1H, td, J = 7.3, 1.1), 6.87-6.72 (2H, m),
4.36-4.313 (2H, m), 3.75-3.68 (2H, m), 3.44 (3H,
s), 2.29 (3H, s), 2.25, (3H, s), 2.15 (3H, s), 2.13
(3H, s), 1.63 (3H, s), 1.57 (3H, s). Physical properties: gum-like.

[0444]

Working Example 162 2-Methylsulfonylbenzoic acid = 5,5-dimethyl-1-methoxyethoxy-2
-Oxo-3- (2,4,6-trimethylphenyl)-
2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 1-452) ¹ H-NMR (CDCl ₃ ) δ (ppm): 8.11-8.06 (1H, m), 7.70-7.5
7 (2H, m), 7.09-7.04 (1H, m), 6.90 (2H, s), 4.36-
4.11 (2H, m), 3.76-3.71 (2H, m), 3.44 (3H, s), 3.2
1 (3H, s), 2.26 (3H, s), 2.24 (6H, s), 1.63 (6H,
s). Physical properties: amorphous.

[0445]

Working Example 163 2-Phenoxymethylbenzoic acid = 5,5-dimethyl-1-methoxyethoxy-2
-Oxo-3- (2,4,6-trimethylphenyl)-
2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 1-453) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.94 (1H, dd, J = 7.9, 1.3),
7.73 (1H, d, J = 7.7), 7.58 (1H, t, J = 7.0), 7.41-7.2
4 (3H, m), 6.96 (1H, t, J = 7.3), 6.83 (2H, dd, J = 9.
0, 1.1), 6.77 (2H, s), 5.07 (2H, s), 4.35-4.31 (2
H, m), 3.75-3.71 (2H, m), 3.44 (3H, s), 2.19 (6H,
s), 2.10 (3H, s), 1.59 (6H, s). Physical properties: Crystal (melting point: 66-68 ° C).

[0446]

Working Example 164 2-Methoxycarbonylbenzoic acid = 5,5-dimethyl-1-methoxyethoxy-
2-oxo-3- (2,4,6-trimethylphenyl)
-2,5-Dihydro-1H-pyrrol-4-yl ester (Compound No. 1-454) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.80-7.75 (1H, m), 7.58-7.4
4 (2H, m), 7.18-7.13 (1H, m), 6.86 (2H, s), 4.36-
4.31 (2H, m), 3.80 (3H, s), 3.76-3.71 (2H, m), 3.4
4 (3H, s), 2.25 (3H, s), 2.19 (6H, s), 1.62 (6H,
s). Physical properties: Crystal (melting point: 146-149 ° C).

[0447]

Example 165 2-Phenoxybenzoic acid = 5,5-dimethyl-1-methoxyethoxy-2-oxo-3- (2,4,6-trimethylphenyl) -2,5
-Dihydro-1H-pyrrol-4-yl ester (Compound No. 1-455) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.73 (1H, dd, J = 7.9, 1.65),
7.51-7.26 (3H, m), 7.16-7.09 (2H, m), 6.90 (3H, m
d, J = 8.8), 6.77 (2H, s), 4.28 (2H, t, J = 4.6), 3.69
(2H, t, J = 4.6), 3.41 (3H, s), 2.21 (3H, s), 2.15
(6H, s), 1.42 (6H, s). Physical properties: crystals (melting point: 115-116 ° C).

[0448]

Working Example 166 2-ethoxybenzoic acid =
5,5-dimethyl-1-methoxyethoxy-2-oxo-3- (2,4,6-trimethylphenyl) -2,5-
Dihydro-1H-pyrrol-4-yl ester (Compound No. 1-456) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.61 (1H, dd, J = 8.1, 1.8),
7.46 (1H, td, J = 8.1, 1.8), 6.95-6.88 (2H, m), 6.81
(2H, s), 4.35-4.30 (2H, m), 4.06 (2H, q, J = 7.0),
3.75-3.71 (2H, m), 3.44 (3H, s), 2.21 (9H, s), 1.5
7 (6H, s), 1.38 (3H, t, J = 7.0). Physical properties: crystals (melting point: 89-91 ° C).

[0449]

Example 167 2-propyloxybenzoic acid = 5,5-dimethyl-1-methoxyethoxy-2-
Oxo-3- (2,4,6-trimethylphenyl)-
2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 1-457) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.62 (1H, dd, J = 8.1, 1.8),
7.50-7.41 (1H, m), 6.95-6.88 (2H, m), 6.80 (2H,
s), 4.32 (2H, t, J = 4.6), 3.94 (2H, t, J = 6.4), 3.73
(2H, t, J = 4.6), 3.44 (3H, s), 2.21 (9H, s), 1.77
(2H, q, J = 7.0), 1.57 (6H, s), 0.98 (3H, t, J = 7.
3). Physical properties: crystals (melting point: 94-96 ° C).

[0450]

Working Example 168 2-acetoxybenzoic acid = 5,5-dimethyl-1-methoxyethoxy-2-oxo-3- (2,4,6-trimethylphenyl) -2,5
-Dihydro-1H-pyrrol-4-yl ester (Compound No. 1-458) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.88 (1H, dd, J = 8.1, 1.8),
7.59 (1H, td, J = 8.1, 1.8), 7.34-7.31 (1H, m), 7.08
(1H, d, J = 7.3), 6.81 (2H, s), 4.34-4.30 (2H, m),
3.75-3.70 (2H, m) 3.44 (3H, s), 2.21 (3H, s), 2.19
(9H, s), 1.56 (6H, s). Physical properties: crystals (melting point: 105-107 ° C).

[0451]

Working Example 169 2-Methylnicotinic Acid =
5,5-dimethyl-1-methoxyethoxy-2-oxo-3- (2,4,6-trimethylphenyl) -2,5-
Dihydro-1H-pyrrol-4-yl ester (Compound No. 1-459) ¹ H-NMR (CDCl ₃ ) δ (ppm): 8.64 (1H, dd, J = 4.8, 1.8),
8.08 (1H, dd, J = 8.1, 1.8), 7.28-7.20 (1H, m), 6.82
(2H, s), 4.37-4.33 (2H, m), 3.77-3.72 (2H, m), 3.4
5 (3H, s), 2.59 (3H, s), 2.24 (3H, s), 2.21 (6H,
s), 1.60 (6H, s). Physical properties: Crystal (melting point: 73-74 ° C).

[0452]

Example 170 4-trifluoromethylnicotinic acid = 5,5-dimethyl-1-methoxyethoxy-
2-oxo-3- (2,4,6-trimethylphenyl)
-2,5-Dihydro-1H-pyrrol-4-yl ester (Compound No. 1-460) ¹ H-NMR (CDCl ₃ ) δ (ppm): 8.93 (1H, d, J = 5.2), 8.63
(1H, s), 7.64 (1H, d, J = 5.2), 6.86 (2H, s), 4.36-
4.31 (2H, m), 3.75-3.70 (2H, m), 3.44 (3H, s), 2.24
(3H, s), 2.19 (6H, s), 1.58 (6H, s). Physical properties: crystals (melting point: 102-104 ° C).

[0453]

Example 171 2-Methylthio-4-trifluoromethylpyrimidine-5-carboxylic acid = 5
5-dimethyl-1-methoxyethoxy-2-oxo-3
-(2,4,6-trimethylphenyl) -2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 1-461) ¹ H-NMR (CDCl ₃ ) δ (ppm): 8.62 (1H , s), 6.84 (2H, s),
4.33 (2H, t, J = 4.6), 3.72 (2H, t, J = 4.6), 3.44 (3
H, s), 2.63 (3H, s), 2.24 (3H, s), 2.17 (6H, s), 1.
57 (6H, s). Physical properties: crystals (melting point: 118-120 ° C).

[0454]

Example 172 5-Chloro-1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxylic acid = 5,5-dimethyl-1-methoxyethoxy-2-oxo-3- (2,4 , 6-Trimethylphenyl) -2,5-dihydro-1H-pyrrol-4-yl =
Ester (Compound No. 1-462) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.81 (2H, s), 4.34-4.30 (2
H, m), 3.90 (3H, s), 3.74-3.70 (2H, s), 3.43 (3H,
s), 2.22 (3H, s), 2.05 (6H, s), 1.55 (6H, s). Physical properties: gum-like.

[0455]

Working Example 173 4-Methyl- [1,2,3] thiadiazole-5-carboxylic acid = 5,5-dimethyl-1-methoxyethoxy-2-oxo-3- (2
4,6-trimethylphenyl) -2,5-dihydro-1
H-pyrrol-4-yl ester (Compound No. 1-4
63) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.81 (2H, s), 4.35-4.31 (2
H, m), 3.74-3.70 (2H, m), 3.43 (3H, s), 2.83 (3H,
s), 2.21 (3H, s), 2.17 (6H, s), 1.57 (6H, s). Physical properties: Crystal (melting point: 72-74 ° C).

[0456]

Example 174 5,5-Dimethyl-4-benzyloxy-1-methoxyethoxy-2-oxo-3- (2
4,6-trimethylphenyl) -2,5-dihydro-1
H-pyrrole (Compound No. 1-464) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.31-7.26 (3H, m), 7.05-7.0
2 (2H, m), 6.86 (2H, s), 4.67 (2H, s), 4.24 (2H,
t, J = 4.8), 3.69 (2H, t, J = 4.6), 3.42 (3H, s), 2.28
(3H, s), 2.10 (6H, s), 1.51 (6H, s). Physical properties: oil.

[0457]

Example 175 5,5-Dimethyl-4- (4-methoxybenzyloxy) -1-methoxyethoxy-2-oxo-3- (2,4,6-trimethylphenyl) -2,5
-Dihydro-1H-pyrrole (Compound No. 1-465) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.97 (2H, d, J = 8.8), 6.87
(2H, s), 6.81 (2H, d, J = 8.8), 4.59 (2H, s), 4.25-
4.21 (2H, m), 3.79 (3H, s), 3.71-3.66 (2H, m), 3.41
(3H, s), 2.28 (3H, s), 2.12 (6H, s), 1.61 (6H,
s). Physical properties: oil.

[0458]

Example 176 5,5-Dimethyl-4-ethoxymethoxy-1-methoxyethoxy-2-oxo-3- (2,5
4,6-trimethylphenyl) -2,5-dihydro-1
H-pyrrole (Compound No. 1-466) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.85 (2H, s), 4.72 (2H, s),
4.27-4.22 (2H, m), 3.77-3.67 (2H, m), 3.59 (2H,
q, J = 7.0), 3.42 (3H, s), 2.26 (3H, s), 2.14 (6H,
s), 1.50 (6H, s), 1.16 (3H, t, J = 7.0). Physical properties: oil.

[0459]

EXAMPLE 177 Cyclopropanecarboxylic acid = 5,5-dimethyl-1-methoxy-2-oxo-
3- (2,4,6-trimethylphenyl) -2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 1-467) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.84 ( 2H, s), 3.99 (3H, s),
2.25 (3H, s), 2.15 (6H, s), 1.68-1.54 (1H, m), 1.
50 (6H, s), 0.95-0.78 (4H, m). Physical properties: Crystal (melting point: 86-87 ° C).

[0460]

Example 178: 5-Allyl-4-hydroxy-5-methyl-1-methoxymethoxy-2-oxo-3- (2
4,6-trimethylphenyl) -2,5-dihydro-1
H-pyrrole (Compound No. 1-468) ¹ H-NMR (DMSO-d ₆ ) δ (ppm): 11.34 (1H, s), 6.84 (2H,
s), 5.72-5.55 (1H, m), 5.16-5.04 (2H, m), 4.90 (2H,
ABq, J = 7.3), 3.47 (3H, s), 2.27 (3H, s), 2.03 (6
H, s), 1.41 (3H, s). Physical properties: crystals (melting point: 128-130 ° C).

[0461]

Example 179 Cyclopropanecarboxylic reed
Dd = 5-allyl-5-methyl-1-methoxymethoxy
-2-oxo-3- (2,4,6-trimethylphenyi
) -2,5-dihydro-1H-pyrrol-4-yl =
Ester (Compound No. 1-469) ¹ H-NMR (CDCl_Three) δ (ppm): 6.83 (2H, s), 5.85-5.68 (1
H, m), 5.23-5.11 (2H, m), 5.06 (2H, s), 3.61 (3H,
s), 2.70 (1H, dd, J = 14.3, 6.6), 2.51 (1H, dd, J = 14.
3, 7.7), 2.24 (3H, s), 2.14 (6H, s), 1.71-1.51 (1
H, m), 1.52 (3H, s), 0.92-0.77 (4H, m). Physical properties: oil.

[0462]

Example 180 5-Cyclohexylmethyl-4-hydroxy-5-methyl-1-methoxymethoxy-2-oxo-3- (2,4,6-trimethylphenyl) -2,5
-Dihydro-1H-pyrrole (Compound No. 1-470) ¹ H-NMR (DMSO-d ₆ ) δ (ppm): 11.34 (1H, s), 6.86 (1H,
s), 4.87 (2H, ABq, J = 7.3), 3.46 (3H, s), 2.24 (3H,
s), 2.20-2.18 (2H, m), 2.09 (3H, s), 2.02 (3H,
s), 1.81-0.80 (14H, m). Physical properties: amorphous.

[0463]

Working Example 181 4-Hydroxy-5- (2-phenylethyl) -5-methyl-1-methoxymethoxy-2-oxo-3- (2,4,6-trimethylphenyl) -2,
5-dihydro-1H-pyrrole (Compound No. 1-47
1) ¹ H-NMR (CDCl ₃ ) δ (ppm): 11.53 (1H, s), 7.33-7.15 (5
H, m), 6.88 (2H, s), 4.95 (2H, ABq, J = 7.7), 3.48
(3H, s), 2.25 (3H, s), 2.11 (3H, s), 2.07 (3H, s),
2.68-1.91 (4H, m). Physical properties: amorphous.

[0464]

Working Example 182 5- (3-Butenyl) -4-hydroxy-5-methyl-1-methoxymethoxy-2-oxo-
3- (2,4,6-trimethylphenyl) -2,5-dihydro-1H-pyrrole (Compound No. 1-472) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.87 (2H, s), 5.91 -5.73 (1
H, m), 5.08-4.87 (4H, m), 3.56 (3H, s), 2.26 (3H,
s), 2.15 (3H, s), 2.12 (3H, s), 2.03-1.84 (4H, m),
1.51 (3H, s). Physical properties: oil.

[0465]

Working Example 183 4-Hydroxy-5-methyl-5-methoxyethyl-1-methoxymethoxy-2-oxo-3
-(2,4,6-trimethylphenyl) -2,5-dihydro-1H-pyrrole (Compound No. 1-473) ¹ H-NMR (DMSO-d ₆ ) δ (ppm): 11.44 (1H, s), 6.86 (2H,
s), 4.88 (2H, ABq, J = 7.3), 3.50 (3H, s), 3.18 (3H,
s), 2.26-1.91 (13H, m), 1.41 (3H, s). Physical properties: oil.

[0466]

Example 184 4-Hydroxy-5-methyl-5-methoxyethoxyethyl-1-methoxymethoxy-2-oxo-3- (2,4,6-trimethylphenyl) -2,
5-dihydro-1H-pyrrole (Compound No. 1-47
4) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.89 (2h, s), 5.08 (2H, s),
3.74-3.68 (2H, m), 3.59-3.51 (7H, m), 3.38 (3H,
s), 2.25 (3H, s), 2.15 (6H, s), 1.98 (3H, t, J = 7.
0), 1.53 (3H, s). Physical properties: amorphous.

[0467]

Working Example 185 4-Hydroxy-1-methoxymethoxy-3- (2,4,6-trimethylphenyl) -1-azaspiro [4.4] nonan-3-en-2-one (Compound No. 1-475) ) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.91 (2H, s), 5.04 (2H, s),
3.58 (3H, s), 2.28 (3H, s), 2.14 (6H, s), 2.28-1.8
5 (8H, m). Physical properties: Crystal (melting point: 149-151 ° C).

[0468]

Example 186 2,2-Dimethylpropionic acid = 5,5-dimethyl-1-hydroxy-2-oxo-3- (2,4-dichlorophenyl) -2,5-dihydro-1H-pyrrole-4 -Yl = ester (Compound No. 2-1) ¹ H-NMR (CDCl ₃ ) δ (ppm): 10.1 (1H, brd.s), 7.41-7.40
(1H, m), 7.26-7.24 (2H, m), 1.45 (6H, s), 1.19 (9
H, s). Physical properties: crystals (melting point: 178-179 ° C).

[0469]

Working Example 187 5,5-Dimethyl-4-hydroxy-
1-methoxy-2-oxo-3- (2,4-dichlorophenyl) -2,5-dihydro-1H-pyrrole (Compound No. 2-2) ¹ H-NMR (CD ₃ OD) δ (ppm): 7.52 ( 1H, d, J = 2.0), 7.40-7.
25 (2H, m), 3.92 (3H, s), 1.50 (6H, s). Physical properties: Crystal (melting point: 199-201 ° C).

[0470]

Working Example 188 2,2-Dimethylpropionic acid = 5,5-dimethyl-1-methoxy-2-oxo-
3- (2,4-dichlorophenyl) -2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 2
-3) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.40 (1H, brd.s), 7.29 (2H,
brd.s), 4.00 (3H, s), 1.49 (2H, s), 1.20 (9H, s). Physical properties: oil.

[0471]

Working Example 189 5,5-Dimethyl-4-hydroxy-
1-ethoxy-2-oxo-3- (2,4-dichlorophenyl) -2,5-dihydro-1H-pyrrole (Compound No. 2-5) ¹ H-NMR (DMSO-d ₆ ) δ (ppm): 7.62 (1H, d, J = 1.1), 7.41
(1H, m), 7.29 (1H, d, J = 8.1), 4.02 (2H, q, J = 7.0),
1.38 (6H, s), 1.22 (3H, t, J = 7.0). Physical properties: crystals (melting point: 170-172 ° C).

[0472]

Example 190 2,2-Dimethylpropionic acid = 5,5-dimethyl-1-ethoxy-2-oxo-
3- (2,4-dichlorophenyl) -2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 2
−6) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.41 (1H, m), 7.30-7.26 (2H,
m), 4.22 (2H, q, J = 7.0), 1.51 (6H, s) 1.35 (3H,
t, J = 7.0), 1.20 (9H, s). Physical properties: oil.

[0473]

Example 191 5,5-Dimethyl-4-hydroxy-
1-methoxymethoxy-2-oxo-3- (2,4-dichlorophenyl) -2,5-dihydro-1H-pyrrole (Compound No. 2-8) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.65 ( 1H, d, J = 1.8), 7.43 (1
H, dd, J = 8.4, 2.2), 7.31 (1H, brd.s), 4.89 (2H,
s), 3.47 (3H, s), 1.40 (6H, s). Physical properties: Crystal (melting point: 148-150 ° C).

[0474]

Example 192 2,2-Dimethylpropionic acid = 5,5-dimethyl-1-methoxymethoxy-2-
Oxo-3- (2,4-dichlorophenyl) -2,5-
Dihydro-1H-pyrrol-4-yl ester (Compound No. 2-9) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.40 (1H, m), 7.29 (2H, m),
5.04 (2H, s), 3.62 (3H, s), 1.49 (6H, s), 1.24 (9
H, s). Physical properties: oil.

[0475]

Working Example 193 5,5-Dimethyl-4-hydroxy-
1-ethoxymethoxy-2-oxo-3- (2,4-dichlorophenyl) -2,5-dihydro-1H-pyrrole (Compound No. 2-11) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.64 ( 1H, d, J = 1.8), 7.42 (1
H, dd, J = 8.1, 2.2), 7.29 (1H, d, J = 8.4), 4.93 (2H,
s), 3.75 (2H, q, J = 7.0), 1.39 (6H, s), 1.17 (3H,
t, H = 7.0). Physical properties: crystals (melting point: 166-168 ° C).

[0476]

Example 194 2,2-Dimethylpropionic acid = 5,5-dimethyl-1-ethoxymethoxy-2-
Oxo-3- (2,4-dichlorophenyl) -2,5-
Dihydro-1H-pyrrol-4-yl ester (Compound No. 2-12) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.40 (1H, m), 7.29-7.28 (2H,
m), 5.10 (2H, s), 3.88 (2H, q, J = 7.0), 1.56 (6H,
s), 1.29 (3H, t, J = 7.0), 1.20 (9H, s). Physical properties: oil.

[0477]

Working Example 195: 5,5-Dimethyl-4-hydroxy-
1-methoxyethoxy-2-oxo-3- (2,4-dichlorophenyl) -2,5-dihydro-1H-pyrrole (Compound No. 2-14) ¹ H-NMR (DMSO-d ₆ ) δ (ppm): 11.86 (1H, s), 7.64 (1H,
d, J = 1.8), 7.43 (1H, dd, J = 6.2, 1.8), 7.28 (1H, d,
J = 6.2), 4.09 (2H, dd, J = 4.4, 1.8), 3.57 (2H, dd,
J = 4.4, 1.8), 3.23 (3H, s), 1.39 (6H, s). Physical properties: Crystal (melting point: 139.0-139.5 ° C).

[0478]

Working Example 196: 5,5-Dimethyl-4-hydroxy-
1-methoxy-2-oxo-3- (2-chloro-4-methylphenyl) -2,5-dihydro-1H-pyrrole (Compound No. 2-18) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.23 (1H, brd.s), 4.49 (1H,
s), 4.04 (3H, s), 2.33 (3H, s), 1.55 (3H, s), 1.51
(3H, s). Physical properties: amorphous.

[0479]

Example 197 2,2-Dimethylpropionic acid = 5,5-dimethyl-1-methoxy-2-oxo-
3- (2-chloro-4-methylphenyl) -2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 2-19) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.24- 7.20 (2H, m), 7.10-7.06
(1H, m), 4.00 (3H, s), 2.32 (3H, s), 1.48 (6H,
s), 1.18 (9H, s). Physical properties: oil.

[0480]

Working Example 198: Dithiocarbonic acid = S-ethyl ester =
O- [5,5-dimethyl-1-methoxy-2-oxo-
3- (2-Chloro-4-methylphenyl) -2,5-dihydro-1H-pyrrol-4-yl] ester (Compound No. 2-20) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.20- 7.16 (2H, m), 7.09-7.04
(1H, m), 4.01 (3H, s), 3.03 (2H, q, J = 7.3), 2.30
(3H, s), 1.55 (6H, s), 1.23 (3H, t, J = 7.3). Physical properties: oil.

[0481]

Working Example 199 2,2-Dimethylpropionic acid = 5,5-dimethyl-1-ethoxy-2-oxo-
3- (2-chloro-4-methylphenyl) -2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 2-22) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.24- 7.19 (2H, m), 7.10-7.05
(1H, m), 4.21 (2H, q, J = 7.3), 2.32 (3H, s), 1.47
(6H, s), 1.36 (3H, t, J = 7.3), 1.18 (9H, s). Physical properties: Crystal (melting point: 103-104 ° C).

[0482]

Example 200 Dithiocarbonate = S-ethyl ester =
O- [5,5-dimethyl-1-ethoxy-2-oxo-
3- (2-Chloro-4-methylphenyl) -2,5-dihydro-1H-pyrrol-4-yl] ester (Compound No. 2-23) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.20- 7.16 (2H, m), 7.09-7.03
(1H, m), 4.22 (2H, q, J = 7.0), 3.04 (2H, q, J = 7.7),
2.30 (3H, s), 1.54 (6H, s), 1.37 (3H, t, J = 7.0),
1.24 (3H, t, J = 7.7). Physical properties: oil.

[0483]

Example 201 5,5-Dimethyl-4-hydroxy-
1-methoxymethoxy-2-oxo-3- (2-chloro-4-methylphenyl) -2,5-dihydro-1H-pyrrole (Compound No. 2-24) ¹ H-NMR (CDCl ₃ ) δ (ppm) : 7.27-7.24 (1H, m), 7.06-7.00
(2H, m), 5.11 (2H, s), 3.62 (3H, s), 2.33 (3H, s),
1.53 (6H, s). Physical properties: Crystal (melting point: 153-158 ° C).

[0484]

Example 202 2,2-Dimethylpropionic acid = 5,5-dimethyl-1-methoxymethoxy-2-
Oxo-3- (2-chloro-4-methylphenyl)-
2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 2-25) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.26-7.24 (1H, m), 7.20 (1H,
brd.s), 7.11-7.06 (1H, m), 5.05 (2H, s), 3.62 (3
H, s), 2.32 (3H, s), 1.48 (6H, s), 1.19 (9H, s). Physical properties: oil.

[0485]

Working Example 203 Dithiocarbonic acid = S-ethyl ester =
O- [5,5-dimethyl-1-methoxymethoxy-2-
Oxo-3- (2-chloro-4-methylphenyl)-
2,5-Dihydro-1H-pyrrol-4-yl] ester (Compound No. 2-26) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.20-7.16 (2H, m), 7.09-7.04
(1H, m), 5.06 (2H, s), 3.63 (3H, s), 3.03 (2H, q,
J = 7.7), 2.30 (3H, s), 1.55 (6H, s), 1.23 (3H, t,
J = 7.7). Physical properties: oil.

[0486]

Example 204 5,5-dimethyl-4-hydroxy-
1-methoxy-2-oxo-3- (2,6-dimethyl-
4-bromophenyl) -2,5-dihydro-1H-pyrrole (Compound No. 2-34) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.25 (2H, s), 6.20 (1H, brd.
s), 3.95 (3H, s), 2.15 (6H, s), 1.51 (6H, s). Physical properties: crystals (melting point: 234-235 ° C).

[0487]

Example 205 5,5-Dimethyl-4-hydroxy-
1-methoxymethoxy-2-oxo-3- (4-bromo-2,6-dimethylphenyl) -2,5-dihydro-1
H-pyrrole (Compound No. 2-40) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.26 (2H, s), 4.99 (2H, s),
3.58 (3H, s), 2.14 (6H, s), 1.50 (6H, s). Physical properties: Crystal (melting point: 183-185 ° C).

[0488]

Working Example 206 5,5-Dimethyl-4-hydroxy-
1-methoxyethoxy-2-oxo-3- (4-bromo-2,6-dimethylphenyl) -2,5-dihydro-1
H-pyrrole (Compound No. 2-46) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.27 (2H, s), 4.11 (2H, t,
J = 4.4), 3.60 (2H, t, J = 4.4), 3.36 (3H, s), 2.02 (6
H, s), 1.39 (6H, s). Physical properties: crystals (melting point: 161-162 ° C).

[0489]

Example 207 5,5-dimethyl-4-hydroxy-
1-methoxy-2-oxo-3- (2,3-dimethylphenyl) -2,5-dihydro-1H-pyrrole (Compound No. 2-50) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.15- 7.07 (2H, m), 4.06 (3H,
s), 2.30 (3H, s), 2.25 (3H, s), 1.50 (6H, s). Physical properties: crystals (melting point: 167-168 ° C).

[0490]

Working Example 208 5,5-Dimethyl-4-hydroxy-
1-methoxy-2-oxo-3- (2,4-dimethylphenyl) -2,5-dihydro-1H-pyrrole (Compound No. 2-66) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.06- 6.94 (3H, m), 4.00 (3H,
s), 3.63 (3H, s), 2.31 (3H, s), 2.23 (3H, s), 1.5
1 (6H, s). Physical properties: oil.

[0490]

Working Example 209 5,5-Dimethyl-4-hydroxy-
1-methoxy-2-oxo-3- (2,5-dimethylphenyl) -2,5-dihydro-1H-pyrrole (Compound No. 2-82) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.14- 7.00 (3H, m), 6.15 (1H,
brd.s), 3.96 (3H, s), 2.31 (3H, s), 2.20 (3H, s),
1.51 (6H, s). Physical properties: Crystal (melting point: 49-50 ° C).

[0492]

Example 210 5,5-Dimethyl-4-hydroxy-
1-methoxymethoxy-2-oxo-3- (2,5-dimethylphenyl) -2,5-dihydro-1H-pyrrole (Compound No. 2-88) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.15 (1H, d, J = 7.8), 7.07 (1
H, d, J = 7.8), 6.99 (1H, s), 6.50 (1H, bs), 5.01 (2
H, s), 3.60 (3H, s), 2.31 (3H, s), 2.19 (3H, s), 1.
51 (6H, s). Physical properties: crystals (melting point: 121-122 ° C).

[0493]

Example 211 2,2-Dimethylpropionic acid = 5,5-dimethyl-1-methoxymethoxy-2-
Oxo-3- (2,5-dimethylphenyl) -2,5-
Dihydro-1H-pyrrol-4-yl ester (Compound No. 2-89) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.09-7.00 (2H, m), 6.88 (1
H, s), 5.04 (2H, s), 3.61 (3H, s), 2.25 (3H, s),
2.21 (3H, s), 1.47 (6H, s), 1.11 (9H, s). Physical properties: amorphous.

[0494]

Example 212 5,5-Dimethyl-4-hydroxy-
1-methoxy-2-oxo-3- (2,6-dimethylphenyl) -2,5-dihydro-1H-pyrrole (Compound No. 2-98) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.21- 7.04 (3H, s), 3.72 (3H,
s), 2.19 (6H, s), 152 (6H, s). Physical properties: oil.

[0495]

Working Example 213: 5,5-Dimethyl-4-hydroxy-
1-methoxymethoxy-2-oxo-3- (2,6-dimethylphenyl) -2,5-dihydro-1H-pyrrole (Compound No. 2-104) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.0 -7.2 (3H, m), 4.99 (2H,
s), 3.58 (3H, s), 2.16 (6H, s), 1.51 (6H, s). Physical properties: crystals (melting point: 154-155 ° C).

[0496]

Example 214 2,2-Dimethylpropionic acid = 5,5-dimethyl-1-methoxymethoxy-2-
Oxo-3- (2,6-dimethylphenyl) -2,5-
Dihydro-1H-pyrrol-4-yl ester (Compound No. 2-105) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.95-7.15 (3H, m), 5.06 (2H,
s), 3.62 (3H, s), 2.20 (6H, s), 1.49 (6H, s), 1.0
6 (9H, s). Physical properties: crystals (melting point: 82-83 ° C).

[0497]

Example 215 1-ethoxymethoxy-5,5-dimethyl-4-hydroxy-2-oxo-3- (2,6-dimethylphenyl) -2,5-dihydro-1H-pyrrole (Compound No. 2-107) ) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.20-7.05 (3H, m), 6.47 (1
H, brd.s), 5.06 (2H, s), 3.85 (2H, q, J = 7.2), 2.17
(6H, s), 1.52 (6H, s), 1.29 (3H, t, J = 7.2). Physical properties: Crystal (melting point: 122-123 ° C).

[0498]

Working Example 216 2,2-Dimethylpropionic Acid = 1-ethoxymethoxy-5,5-dimethyl-2-
Oxo-3- (2,6-dimethylphenyl) -2,5-
Dihydro-1H-pyrrol-4-yl ester (Compound No. 2-108) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.13-6.98 (3H, m), 5.11 (2
H, s), 3.88 (2H, q, J = 6.9), 2.20 (6H, s), 1.50 (6
H, s), 1.29 (3H, t, J = 6.9), 1.06 (9H, s). Physical properties: crystals (melting point: 119-120 ° C).

[0499]

Example 217 5,5-dimethyl-4-hydroxy-
1-methoxyethoxy-2-oxo-3- (2,6-dimethylphenyl) -2,5-dihydro-1H-pyrrole (Compound No. 2-110) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.16 -7.02 (3H, m) 4.26-4.16
(2H, m) 3.72-3.62 (2H, m) 3.40 (3H, s) 2.15 (6H,
s) 1.50 (6H, s). Physical properties: Crystal (melting point: 107-109 ° C).

[0500]

Example 218 2,2-Dimethylpropionic acid = 5,5-dimethyl-1-methoxyethoxy-2-
Oxo-3- (2,6-dimethylphenyl) -2,5-
Dihydro-1H-pyrrol-4-yl ester (Compound No. 2-111) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.15-6.95 (3H, m) 4.35-4.27
(2H, m) 3.75-3.68 (2H, m) 3.43 (3H, s) 2.20 (6H,
s) 1.50 (6H, s) 1.05 (9H, s). Physical properties: oil.

[0501]

Working Example 219 Dithiocarbonic acid = S-ethyl ester =
O- [5,5-dimethyl-1-methoxyethoxy-2-
Oxo-3- (2,6-dimethylphenyl) -2,5-
Dihydro-1H-pyrrol-4-yl] ester (Compound No. 2-112) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.13-6.93 (3H, m) 4.33-4.28
(2H, m) 3.73-3.68 (2H, m) 3.43 (3H, s) 2,96 (2H, m
q, J = 7.3) 2.21 (6H, s) 1.58 (6H, s) 1.15 (3H, t, J
= 7.3). Physical properties: oil.

[0502]

Example 220 5,5-Dimethyl-4-hydroxy-
1-methoxy-2-oxo-3- (2-methyl-4-bromophenyl) -2,5-dihydro-1H-pyrrole (Compound No. 2-114) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.41-7.26 (2H, m), 6.87-6.81
(1H, m), 4.06 (3H, s), 2.36 (3H, s), 1.51 (6H,
s). Physical properties: crystals (melting point: 193-194 ° C).

[0503]

Example 221 5,5-Dimethyl-4-hydroxy-
1-methoxymethoxy-2-oxo-3- (2-methyl-6-chlorophenyl) -2,5-dihydro-1H-pyrrole (Compound No. 2-136) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.05-7.25 (3H, m), 4.97 (2H,
s), 3.57 (3H, s), 2.20 (3H, s), 1.51 (3H, s), 1.4
8 (3H, s). Physical properties: crystals (melting point: 169-171 ° C).

[0504]

Example 222 2,2-Dimethylpropionic acid = 5,5-dimethyl-1-methoxymethoxy-2-
Oxo-3- (2-methyl-6-bromophenyl)-
2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 2-137) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.07-7.25 (3H, m), 5.06 (2H,
s), 3.62 (3H, s), 2.30 (3H, s), 1.55 (3H, s), 1.4
6 (3H, s), 1.11 (9H, s). Physical properties: oil.

[0505]

Working Example 223: 5,5-Dimethyl-4-hydroxy-
1-methoxyethoxy-2-oxo-3- (2-methyl-6-chlorophenyl) -2,5-dihydro-1H-pyrrole (Compound No. 2-142) ¹ H-NMR (CDCl ₃ ) δ (ppm) : 7.25-7.00 (3H, m), 4.25-4.1
7 (2H, m), 3.72-3.62 (2H, m), 3.41 (3H, s), 2.20
(3H, s), 1.49 (6H, s). Physical properties: crystals (melting point: 137-140 ° C).

[0506]

Example 224 5,5-Dimethyl-4-hydroxy-
1-methoxymethoxy-2-oxo-3- (2-methyl-6-bromophenyl) -2,5-dihydro-1H-pyrrole (Compound No. 2-152) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.42-7.38 (1H, m), 7.13-7.05
(2H, m), 4.95 (2H, s), 3.56 (3H, s), 2.18 (3H,
s), 1.50 (6H, s). Physical properties: crystals (melting point: 145-147 ° C).

[0507]

Working Example 225 2,2-Dimethylpropionic Acid = 5,5-dimethyl-1-methoxymethoxy-2-
Oxo-3- (2-methyl-6-bromophenyl)-
2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 2-153) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.39-7.36 (1H, m), 7.17-7.03
(2H, m), 5.06 (2H, s), 3.62 (3H, s), 2.32 (3H,
s), 1.56 (3H, s), 1.47 (3H, s), 1.12 (9H, s). Physical properties: oil.

[0508]

Example 226 5,5-Dimethyl-4-hydroxy-
1-methoxyethoxy-2-oxo-3- (2-methyl-6-bromophenyl) -2,5-dihydro-1H-pyrrole (Compound No. 2-158) ¹ H-NMR (CDCl ₃ ) δ (ppm) : 7.50-7.38 (1H, m), 7.18-7.05
(2H, m), 4.23-4.19 (2H, m), 3.72-3.64 (2H, m), 3.
40 (3H, s), 2.20 (3H, s), 1.51 (3H, s), 1.48 (3H,
s). Physical properties: amorphous.

[0509]

Example 227 5,5-Dimethyl-4-hydroxy-
1-methoxy-2-oxo-3- (2-methyl-4-methoxyphenyl) -2,5-dihydro-1H-pyrrole (Compound No. 2-162) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.82-6.68 (3H, m), 4.06 (3H,
s), 3.78 (3H, s), 2.34 (3H, s), 1.50 (6H, s). Physical properties: oil.

[0510]

Example 228 5,5-dimethyl-4-hydroxy-
1-methoxy-2-oxo-3- (2-methyl-4-phenylphenyl) -2,5-dihydro-1H-pyrrol-2-one (Compound No. 2-178) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.60-7.29 (8H, m), 4.05 (3H,
s), 2.35 (3H, s), 1.50 (3H, s), 1.49 (3H, s). Physical properties: crystals (melting point: 193-194 ° C).

[0511]

Example 229 5,5-Dimethyl-4-hydroxy-
1-methoxy-2-oxo-3- (2,6-dimethyl-
4-phenylphenyl) -2,5-dihydro-1H-pyrrole (Compound No. 2-194) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.70-7.63 (2H, m), 7.52-7.40
(3H, m), 7.36 (2H, s), 3.84 (3H, s), 2.50 (6H,
s), 1.44 (6H, s). Physical properties: crystals (melting point: 143-145 ° C).

[0512]

Working Example 230 5,5-Dimethyl-4-hydroxy-
1-methoxymethoxy-2-oxo-3- (2,6-dimethyl-4-cyanophenyl) -2,5-dihydro-1
H-pyrrole (Compound No. 2-216) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.24 (2H, s), 4.99 (2H, s),
3.58 (3H, s), 2.21 (6H, s), 1.51 (6H, s). Physical properties: crystals (melting point: 152-154 ° C).

[0513]

Example 231 2,2-Dimethylpropionic acid
Dd = 5,5-dimethyl-1-methoxymethoxy-2-
Oxo-3- (2,6-dimethyl-4-cyanopheni
) -2,5-dihydro-1H-pyrrol-4-yl =
Ester (Compound No. 2-217) ¹ H-NMR (CDCl_Three) δ (ppm): 7.31 (2H, s), 5.04 (2H, s),
3.60 (3H, s), 2.23 (6H, s), 1.49 (6H, s), 1.08 (9
H, s). Physical properties: oil.

[0514]

Example 232 5,5-Dimethyl-4-hydroxy-
1-methoxymethoxy-2-oxo-3- (2,3,6
-Trimethylphenyl) -2,5-dihydro-1H-pyrrole (Compound No. 2-232) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.06 (1H, d, J = 7.7), 6.99
(1H, d, J = 7.7), 5.01 (2H, s), 3.59 (3H, s), 2.24
(3H, s), 2.13 (3H, s), 2.18 (3H, s), 1.53 (3H, s),
1.52 (3H, s). Physical properties: crystals (melting point: 178-180 ° C).

[0515]

Example 233 2,2-dimethylpropionic acid = 5,5-dimethyl-1-methoxymethoxy-2-
Oxo-3- (2,3,6-trimethylphenyl)-
2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 2-233) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.00 (1H, d, J = 7.7), 6.91
(1H, d, J = 7.7), 5.07 (2H, s), 3.63 (3H, s), 2.22
(3H, s), 2.16 (3H, s), 2.10 (3H, s), 1.51 (6H, s),
1.06 (9H, s). Physical properties: crystals (melting point: 79-82 ° C).

[0516]

Working Example 234: 5,5-Dimethyl-4-hydroxy-
1-methoxyethoxy-2-oxo-3- (2,3,6
-Trimethylphenyl) -2,5-dihydro-1H-pyrrole (Compound No. 2-238) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.02 (1H, d, J = 7.7), 6.95
(1H, d, J = 7.7), 4.25-4.15 (2H, m), 3.70-3.60 (2H,
m), 3.39 (3H, s), 2.22 (3H, s), 2.10 (3H, s), 2.06
(3H, s), 1.50 (6H, s). Physical properties: oil.

[0517]

Example 235 2,2-dimethylpropionic acid = 5,5-dimethyl-1-methoxyethoxy-2-
Oxo-3- (2,3,6-trimethylphenyl)-
2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 2-239) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.98 (1H, d, J = 7.7), 6.89
(1H, d, J = 7.7), 4.33-4.27 (2H, m), 3.73-3.67 (2H,
m), 3.43 (3H, s), 2.20 (3H, s), 2.14 (3H, s), 2.09
(3H, s), 1.50 (6H, s), 1.04 (9H, s). Physical properties: oil.

[0518]

Working Example 236 5,5-Dimethyl-4-hydroxy-
1-methoxy-2-oxo-3- (2,3,4,6-tetramethylphenyl) -2,5-dihydro-1H-pyrrole (Compound No. 2-242) ¹ H-NMR (CDCl ₃ ) δ ( ppm): 6.93 (1H, s), 3.97 (3H, s),
2.26 (3H, s), 2.16 (3H, s), 2.11 (6H, s), 1.53 (6
H, s). Physical properties: Crystal (melting point: 182-185 ° C).

[0519]

Working Example 237 2,2-Dimethylpropionic Acid = 5,5-dimethyl-4-hydroxy-1-methoxy-2-oxo-3- (2,3,4,6-tetramethylphenyl) -2 , 5-Dihydro-1H-pyrrole-4-
Il = ester (Compound No. 2-243) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.82 (1H, s), 4.00 (3H, s),
2.21 (3H, s), 2.12 (9H, s), 1.49 (6H, s), 1.05 (9
H, s). Physical properties: crystals (melting point: 104-106 ° C).

[0520]

Working Example 238 5,5-Dimethyl-4-hydroxy-
1-methoxymethoxy-2-oxo-3- (2,3
4,6-tetramethylphenyl) -2,5-dihydro-
1H-pyrrole (Compound No. 2-248) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.88 (1H, s), 6.71 (1H, brd.
s), 4.94 (2H, s), 3.55 (3H, s), 2.34 (3H, s), 2.1
3 (3H, s), 2.06 (6H, s), 1.48 (3H, s), 1.47 (3H,
s). Physical properties: crystals (melting point: 175-176 ° C).

[0521]

Example 239 5,5-Dimethyl-4-hydroxy-
1-methoxyethoxy-2-oxo-3- (2,3,
4,6-tetramethylphenyl) -2,5-dihydro-
1H-pyrrole (Compound No. 2-254) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.89 (1H, s), 4.19 (2H, t, J
= 4.6), 3.64 (2H, t, J = 4.6), 3.38 (3H, s), 2.24 (3
H, s), 2.14 (3H, s), 2.07 (6H, s), 1.50 (3H, s), 1.
49 (3H, s). Physical properties: Crystal (melting point: 144-146 ° C).

[0522]

Working Example 240 5,5-Dimethyl-4-hydroxy-
1-methoxymethoxy-2-oxo-3- (2,4,6
-Trimethyl-3-chlorophenyl) -2,5-dihydro-1H-pyrrole (Compound No. 2-264) ¹ H-NMR (DMSO-d ₆ ) δ (ppm): 11.60 (1H, s), 7.08 (1H,
s), 4.89 (2H, s), 3.48 (3H, s), 2.31 (3H, s), 2.13
(3H, s), 2.03 (3H, s), 1.48 (6H, s). Physical properties: crystals (melting point: 188-189 ° C).

[0523]

Example 241 5,5-dimethyl-4-hydroxy-
1-methoxymethoxy-2-oxo-3- (2,5-dichlorophenyl) -2,5-dihydro-1H-pyrrole (Compound No. 2-279) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.48 ( 1H, d, J = 2.3), 7.35 (1
H, d, J = 8.3), 7.28 (1H, dd, J = 8.3, 2.3), 6.65 (1H,
bs), 5.01 (2H, s), 3.61 (3H, s), 1.51 (6H, s). Physical properties: crystals (melting point: 158-160 ° C).

[0524]

Example 242 5,5-dimethyl-4-hydroxy-
1-methoxymethoxy-2-oxo-3- (2,6-dichlorophenyl) -2,5-dihydro-1H-pyrrole (Compound No. 2-281) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.39- 7.35 (2H, m), 7.28-7.14
(1H, m), 5.02 (2H, s), 3.60 (3H, s), 1.54 (6H,
s). Physical properties: Crystal (melting point: 183-185 ° C).

[0525]

Example 243 2,2-Dimethylpropionic acid = 5,5-dimethyl-1-methoxymethoxy-2-
Oxo-3- (2,6-dichlorophenyl) -2,5-
Dihydro-1H-pyrrol-4-yl ester (Compound No. 2-282) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.36-7.31 (2H, m), 7.24-7.16
(1H, m), 5.07 (2H, s), 3.62 (3H, s), 1.52 (6H,
s), 1.18 (9H, s). Physical properties: Crystal (melting point: 87-88 ° C).

[0526]

Example 244 1-ethoxymethoxy-5,5-dimethyl-4-hydroxy-2-oxo-3- (2,6-dichlorophenyl) -2,5-dihydro-1H-pyrrole (Compound No. 2-284) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.39-7.34 (2H, m), 7.27-7.16
(1H, m), 5.07 (2H, s), 3.85 (2H, q, J = 7.0), 1.53
(6H, s), 1.29 (3H, t, J = 7.3). Physical properties: Crystal (melting point: 170-171 ° C).

[0527]

Example 245 2,2-Dimethylpropionic acid = 5,5-dimethyl-1-ethoxymethoxy-2-
Oxo-3- (2,6-dichlorophenyl) -2,5-
Dihydro-1H-pyrrol-4-yl ester (Compound No. 2-285) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.36-7.31 (2H, m), 7.24-7.16
(1H, m), 5.12 (2H, s), 3.88 (2H, q, J = 7.0), 1.52
(6H, s), 1.29 (3H, t, J = 7.0), 1.17 (9H, s). Physical properties: crystals (melting point: 134-135 ° C).

[0528]

Example 246 2,2-Dimethylpropionic acid = 5,5-dimethyl-1-methoxymethoxy-2-
Oxo-3- (2,5-dichlorophenyl) -2,5-
Dihydro-1H-pyrrol-4-yl ester (Compound No. 2-298) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.33-7.22 (3H, m), 5.04 (2
H, s), 3.62 (3H, s), 1.49 (6H, s), 1.20 (9H, s). Physical properties: crystals (melting point: 133-136 ° C).

[0529]

Example 247 5,5-dimethyl-4-hydroxy-
1-methoxy-2-oxo-3- (3,5-dichlorophenyl) -2,5-dihydro-1H-pyrrole (Compound No. 2-307) ¹ H-NMR (DMSO-d ₆ ): 8.04 (2H, m ), 7.37 (1H, m), 3.82
(3H, s), 1.40 (6H, s). Physical properties: Crystal (melting point: 197-199 ° C).

[0530]

Working Example 248 2,2-Dimethylpropionic Acid = 5,5-dimethyl-1-methoxy-2-oxo-
3- (3,5-dichlorophenyl) -2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 2
−308) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.52 (2H, d, J = 1.8), 7.30 (1
H, t, J = 1.8), 4.00 (3H, s), 1.44 (6H, s), 1.33 (9
H, s). Physical properties: oil.

[0531]

Example 249 5,5-Dimethyl-4-hydroxy-
1-methoxymethoxy-2-oxo-3- (3,5-dichlorophenyl) -2,5-dihydro-1H-pyrrole (Compound No. 2-313) ¹ H-NMR (DMSO-d ₆ ) δ (ppm): 8.03 (1H, t, J = 1.5), 7.39
(1H, t, J = 1.5), 4.91 (2H, s), 3.49 (3H, s), 1.41
(6H, s). Physical properties: Crystal (melting point: 202-203 ° C).

[0532]

Example 250 2,2-Dimethylpropionic acid = 5,5-dimethyl-1-methoxymethoxy-2-
Oxo-3- (3,5-dichlorophenyl) -2,5-
Dihydro-1H-pyrrol-4-yl ester (Compound No. 2-314) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.51 (2H, d, J = 1.8), 7.30 (1
H, t, J = 1.8), 5.04 (2H, s), 3.63 (3H, s), 1.44 (6
H, s), 1.33 (9H, s). Physical properties: oil.

[0533]

Example 251 5,5-Dimethyl-4-hydroxy-
1-methoxymethoxy-2-oxo-3- (2-chloro-6-bromophenyl) -2,5-dihydro-1H-pyrrole (Compound No. 2-329) ¹ H-NMR (DMSO-d ₆ ) δ ( ppm): 7.56 (1H, dd, J = 7.0, 1.
1), 7.53 (1H, dd, J = 7.0,1.1), 7.30 (1H, t, J = 7.0),
4.89 (2H, s), 3.45 (3H, s), 1.41 (6H, s). Physical properties: crystals (melting point: 177-178 ° C).

[0534]

Example 252 2,2-dimethylpropionic acid = 5,5-dimethyl-1-methoxymethoxy-2-
Oxo-3- (2-chloro-6-bromophenyl)-
2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 2-330) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.51 (1H, dd, J = 8.1, 1.1),
7.38 (1H, dd, J = 8.1, 1.1), 7.13 (1H, t, J = 8.1), 5.
07 (2H, s), 3.63 (3H, s), 1.53 (3H, s), 1.52 (3H,
s). Physical properties: Crystal (melting point: 86-87.5 ° C).

[0535]

Working Example 253: 5,5-Dimethyl-4-hydroxy-
1-methoxymethoxy-2-oxo-3- (2-bromophenyl) -2,5-dihydro-1H-pyrrole (Compound No. 2-345) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.62 (1H , d, J = 8.1), 7.41-7.
35 (2H, m), 7.26-7.20 (1H, m), 6.33 (1H, brd.s), 5.
02 (2H, s), 3.61 (3H, s), 1.53 (6H, s).

[0536]

Working Example 254 2,2-Dimethylpropionic Acid = 5,5-dimethyl-1-methoxymethoxy-2-
Oxo-3- (2-bromophenyl) -2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 2-346) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.56 (1H, d, J = 7.9), 7.32-
7.28 (2H, m), 7.21-7.15 (1H, m), 5.05 (2H, s), 3.62
(3H, s), 1.54 (3H, s), 1.45 (3H, s), 1.15 (9H,
s). Physical properties: Crystal (melting point: 83-85 ° C).

[0537]

Working Example 255 5,5-Dimethyl-4-hydroxy-
1-methoxy-2-oxo-3- (2,6-dichloro-
4-trifluoromethylphenyl) -2,5-dihydro-1H-pyrrole (Compound No. 2-371) ¹ H-NMR (DMSO-d ₆ ) δ (ppm): 12.10 (1H, brd.s), 7.97 ( Two
H, s), 3.83 (3H, s), 1.43 (6H, s). Physical properties: crystals (melting point: 242-244 ° C).

[0538]

Working Example 256 5,5-Dimethyl-4-hydroxy-
1-methoxymethoxy-2-oxo-3- (2,6-dichloro-4-trifluoromethylphenyl) -2,5-dihydro-1H-pyrrole (Compound No. 2-377) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.64 (2H, s), 5.02 (2H, s),
3.60 (3H, s), 1.55 (6H, s). Physical properties: Crystal (melting point: 170-171 ° C).

[0539]

Working Example 257 2,2-Dimethylpropionic Acid = 5,5-dimethyl-1-methoxymethoxy-2-
Oxo-3- (2,6-dichloro-4-trifluoromethylphenyl) -2,5-dihydro-1H-pyrrole-4
-Yl = ester (Compound No. 2-378) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.59 (2H, s), 5.06 (2H, s),
3.62 (3H, s), 1.53 (6H, s), 1.20 (9H, s). Physical properties: amorphous.

[0540]

Working Example 258: 5,5-Dimethyl-4-hydroxy-
1-methoxyethoxy-2-oxo-3- (2,6-dichloro-4-trifluoromethylphenyl) -2,5-dihydro-1H-pyrrole (Compound No. 2-380) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.53 (2H, s), 5.15 (2H, s),
3.84 (2H, q, J = 7.0), 1.58 (6H, s), 1.28 (3H, t, J =
7.0). Physical properties: amorphous.

[0541]

Working Example 259 5,5-Dimethyl-4-hydroxy-
1-methoxymethoxy-2-oxo-3- (2,4,6
-Trichlorophenyl) -2,5-dihydro-1H-pyrrole (Compound No. 2-393) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.37 (2H, s), 7.21 (1H, bs),
4.98 (2H, s), 3.58 (3H, s), 1.50 (6H, s). Physical properties: crystals (melting point: 194-195 ° C).

[0542]

Example 260 5,5-Dimethyl-4-hydroxy-
1-methoxymethoxy-2-oxo-3- (2-chlorophenyl) -2,5-dihydro-1H-pyrrole (Compound No. 2-425) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.45-7.36 ( 2H, m), 7.36-7.24
(2H, m), 5.00 (2H, s), 3.60 (3H, s), 1.50 (6H,
s). Physical properties: crystals (melting point: 174-176 ° C).

[0543]

Example 261 2,2-dimethylpropionic acid = 5,5-dimethyl-1-methoxymethoxy-2-
Oxo-3- (2-chlorophenyl) -2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 2-426) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.36-7.26 (4H , m), 5.05 (2
H, s), 3.62 (3H, s), 1.49 (6H, s), 1.17 (9H, s). Physical properties: Crystal (melting point: 78-80 ° C).

[0544]

Working Example 262 Dithiocarbonic acid = S-ethyl ester =
O- [5,5-dimethyl-1-methoxymethoxy-2-
Oxo-3- (2-chlorophenyl) -2,5-dihydro-1H-pyrrol-4-yl] ester (Compound No. 2-427) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.39-7.22 (4H , m), 5.06 (2
H, s), 3.63 (3H, s), 3.02 (2H, q, J = 7.3), 1.56 (6
H, s), 1.22 (3H, t, J = 7.3). Physical properties: Crystal (melting point: 75-79 ° C).

[0545]

Working Example 263 1-Ethoxymethoxy-5,5-dimethyl-4-hydroxy-2-oxo-3- (2-chlorophenyl) -2,5-dihydro-1H-pyrrole (Compound No. 2-428) ¹ H -NMR (CDCl ₃ ) δ (ppm): 7.42-7.10 (4H, m), 5.14 (2
H, s), 4.99 (1H, brd.s), 3.87 (2H, q, J = 7.0), 1.53
(6H, s), 1.27 (3H, t, J = 7.0). Physical properties: crystals (melting point: 119-122 ° C).

[0546]

Working Example 264 2,2-Dimethylpropionic Acid = 1-ethoxymethoxy-5,5-dimethyl-2-
Oxo-3- (2-chlorophenyl) -2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 2-429) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.40-7.22 (4H , m), 5.11 (2
H, s), 3.88 (2H, q, J = 7.0), 1.49 (6H, s), 1.29 (3
H, t, J = 7.0), 1.17 (9H, s). Physical properties: Crystal (melting point: 109-112 ° C).

[0547]

Working Example 265 Dithiocarbonic acid = S-ethyl ester =
O- [1-ethoxymethoxy-5,5-dimethyl-2-
Oxo-3- (2-chlorophenyl) -2,5-dihydro-1H-pyrrol-4-yl] ester (Compound No. 2-430) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.39-7.22 (4H , m), 5.12 (2
H, s), 3.89 (2H, q, J = 7.0), 3.02 (2H, q, J = 7.0),
1.56 (6H, s), 1.30 (3H, t, J = 7.0), 1.22 (3H, t, J =
7.0). Physical properties: oil.

[0548]

Example 266 5,5-Dimethyl-4-hydroxy-
1-methoxyethoxy-2-oxo-3- (2-chlorophenyl) -2,5-dihydro-1H-pyrrole (Compound No. 2-431) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.42-7.10 ( 4H, s), 4.45-4.3
0 (2H, m), 3.75-3.63 (2H, m), 3.42 (3H, s), 1.56
(3H, s), 1.53 (3H, s). Physical properties: crystals (melting point: 131-134 ° C).

[0549]

Working Example 267 2,2-Dimethylpropionic Acid = 5,5-dimethyl-1-methoxyethoxy-2-
Oxo-3- (2-chlorophenyl) -2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 2-432) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.40-7.20 (4H , m), 4.33-4.2
7 (2H, m), 3.75-3.68 (2H, m), 3.43 (3H, s), 1.50
(6H, s), 1.17 (9H, s). Physical properties: oil.

[0550]

Working Example 268 Dithiocarbonate = S-ethyl ester =
O- [5,5-dimethyl-1-methoxyethoxy-2-
Oxo-3- (2-chlorophenyl) -2,5-dihydro-1H-pyrrol-4-yl] ester (Compound No. 2-433) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.34-7.22 (4H , m), 4.34-4.3
0 (2H, m), 3.74-3.70 (2H, m), 3.44 (3H, s), 3.02
(2H, q, J = 7.3), 1.57 (6H, s), 1.22 (3H, t, J = 7.
3). Physical properties: oil.

[0551]

Example 269 5,5-Dimethyl-4-hydroxy-
1-methoxymethoxy-2-oxo-3- (2,5-dibromophenyl) -2,5-dihydro-1H-pyrrole (Compound No. 2-446) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.47 (1H, d, J = 7.8), 7.36-7.
31 (1H, m), 7.26-7.25 (1H, m), 5.01 (2H, s), 3.61
(3H, s), 1.51 (6H, s). Physical properties: crystals (melting point: 162-163 ° C).

[0552]

Example 270 2,2-Dimethylpropionic acid = 5,5-dimethyl-1-methoxymethoxy-2-
Oxo-3- (2,5-dibromophenyl) -2,5-
Dihydro-1H-pyrrol-4-yl ester (Compound No. 2-444) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.45-7.26 (3H, m), 5.05 (2
H, s), 3.62 (3H, s), 1.53 (3H, brd.s), 1.45 (3H, b
rd.s), 1.19 (9H, s). Physical properties: crystals (melting point: 140-143 ° C).

[0553]

Working Example 271 5,5-Dimethyl-4-hydroxy-
1-methoxymethoxy-2-oxo-3- (2,5-dimethylphenyl) -2,5-dihydro-1H-pyrrole (Compound No. 2-473) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.11 (2H, s), 6.94 (1H, s),
5.02 (2H, s), 2.33 (6H, s), 1.46 (6H, s). Physical properties: crystals (melting point: 164-165 ° C).

[0554]

Working Example 272 5,5-Dimethyl-4-hydroxy-
1-methoxymethoxy-2-oxo-3- (3-chloro-2,6-dimethylphenyl) -2,5-dihydro-1
H-pyrrole (Compound No. 2-479) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.23 (1H, d, J = 8.1), 6.97
(1H, d, J = 8.1), 4.96 (2H, s), 3.57 (3H, s), 2.18
(3H, s), 2.09 (3H, s), 1.49 (6H, s). Physical properties: Crystal (melting point: 182-184 ° C).

[0555]

Working Example 273 5,5-Dimethyl-4-hydroxy-
1-methoxymethoxy-2-oxo-3- (2-bromo-4,6-dimethylphenyl) -2,5-dihydro-1
H-pyrrole (Compound No. 2-503) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.29 (1H, s), 7.00 (1H, s),
5.02 (2H, s), 3.59 (3H, s), 2.29 (3H, s), 2.21 (3
H, s), 1.54 (3H, s), 1.51 (3H, s). Physical properties: Crystal (melting point: 148-150 ° C).

[0556]

Example 274 2,2-Dimethylpropionic acid
Dd = 5,5-dimethyl-1-methoxymethoxy-2-
Oxo-3- (2-bromo-4,6-dimethylphenyi
) -2,5-dihydro-1H-pyrrol-4-yl =
Ester (Compound No. 2-504) ¹ H-NMR (CDCl_Three) δ (ppm): 7.21 (1H, s), 6.97 (1H, s),
 5.06 (2H, s), 3.61 (3H, s), 2.26 (6H, s), 1.55 (3
H, s), 1.45 (3H, s), 1.14 (9H, s). Physical properties: oil.

[0557]

Example 275 1-ethoxymethoxy-5,5-dimethyl-4-hydroxy-2-oxo-3- (2-bromo-4,6-dimethylphenyl) -2,5-dihydro-1
H-pyrrole (Compound No. 2-505) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.25 (1H, s), 6.96 (1H, s),
5.01 (2H, s), 3.81 (2H, q, J = 7.0), 2.27 (3H, s),
2.15 (3H, s), 1.48 (3H, s), 1.45 (3H, s), 1.27 (3
H, t, J = 7.0). Physical properties: crystals (melting point: 173-178 ° C).

[0558]

Example 276 2,2-Dimethylpropionic acid
Dd = 1-ethoxymethoxy-5,5-dimethyl-2-
Oxo-3- (2-bromo-4,6-dimethylphenyi
) -2,5-dihydro-1H-pyrrol-4-yl =
Ester (Compound No. 2-506) ¹ H-NMR (CDCl_Three) δ (ppm): 7.20 (1H, s), 6.97 (1H, s),
 5.11 (2H, s), 3.87 (2H, q, J = 7.0), 2.26 (6H, s),
1.54 (3H, s), 1.45 (3H, s), 1.29 (3H, t, J = 7.0),
1.13 (9H, s). Physical properties: oil.

[0559]

Working Example 277 5,5-Dimethyl-4-hydroxy-
1-methoxyethoxy-2-oxo-3- (2-bromo-4,6-dimethylphenyl) -2,5-dihydro-1
H-pyrrole (Compound No. 2-507) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.23 (1H, s), 6.94 (1H, s),
4.25-4.15 (2H, m), 3.70-3.60 (2H, m), 3.37 (3H,
s), 2.25 (3H, s), 2.15 (3H, s), 1.49 (3H, s), 1.46
(3H, s). Physical properties: crystals (melting point: 134-138 ° C).

[0560]

Example 278 2,2-Dimethylpropionic acid
Dd = 5,5-dimethyl-1-methoxyethoxy-2-
Oxo-3- (2-bromo-4,6-dimethylphenyi
) -2,5-dihydro-1H-pyrrol-4-yl =
Ester (Compound No. 2-508) ¹ H-NMR (CDCl_Three) δ (ppm): 7.20 (1H, s), 6.96 (1H, s),
 4.35-4.26 (2H, m), 3.75-3.66 (2H, m), 3.43 (3H,
s), 2.26 (6H, s), 1.55 (3H, s), 1.46 (3H, s), 1.13
(9H, s). Physical properties: oil.

[0561]

Example 279 5,5-dimethyl-4-hydroxy-
1-methoxymethoxy-2-oxo-3- (2,4-dichloro-6-methylphenyl) -2,5-dihydro-1
H-pyrrole (Compound No. 2-509) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.25 (1H, brd.s), 7.12 (1H,
brd.s), 4.96 (2H, s), 3.57 (3H, s), 2.17 (3H, s),
1.49 (3H, s), 1.47 (3H, s). Physical properties: crystals (melting point: 173-175 ° C).

[0562]

Example 280 2,2-Dimethylpropionic acid
Dd = 5,5-dimethyl-1-methoxymethoxy-2-
Oxo-3- (2,4-dichloro-6-methylpheni
) -2,5-dihydro-1H-pyrrol-4-yl =
Ester (Compound No. 2-510) ¹ H-NMR (CDCl_Three) δ (ppm): 7.23 (1H, d, J = 2.2), 7.13
(1H, m), 5.04 (2H, s), 3.61 (3H, s), 2.28 (3H, s),
1.53 (6H, s), 1.23 (9H, s). Physical properties: oil.

[0563]

Working Example 281 5,5-Dimethyl-4-hydroxy-
1-methoxyethoxy-2-oxo-3- (2,4-dichloro-6-methylphenyl) -2,5-dihydro-1
H-pyrrole (Compound No. 2-513) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.18 (1H, brd.s), 7.11 (1H,
m), 4.22-4.17 (2H, m), 3.72-3.59 (2H, m), 3.42 (3
H, s), 2.18 (3H, s), 1.48 (3H, s), 1.46 (3H, s). Physical properties: amorphous.

[0564]

Working Example 282 5,5-Dimethyl-4-hydroxy-
1-methoxymethoxy-2-oxo-3- (2-bromo-5-chlorophenyl) -2,5-dihydro-1H-pyrrole (Compound No. 2-527) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.55-7.10 (3H, m), 5.00 (2
H, s), 3.60 (3H, s), 1.54 (3H, s), 1.50 (3H, s). Physical properties: crystals (melting point: 170-174 ° C).

[0565]

Working Example 283 5,5-Dimethyl-4-hydroxy-
1-methoxymethoxy-2-oxo-3- (2-chloro-6-fluorophenyl) -2,5-dihydro-1H-
Pyrrole (Compound No. 2-528) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.33-7.15 (2H, m), 7.10-6.9
3 (1H, m), 5.10 (2H, s), 3.61 (3H, s), 1.56 (6H,
s). Physical properties: crystals (melting point: 136-142 ° C).

[0566]

Working Example 284 2,2-Dimethylpropionic Acid = 5,5-dimethyl-1-methoxymethoxy-2-
Oxo-3- (2-chloro-6-fluorophenyl)-
2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 2-529) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.33-7.18 (2H, m), 7.07-6.9
5 (1H, m), 5.06 (2H, s), 3.62 (3H, s), 1.52 (3H,
s), 1.50 (3H, s), 1.18 (9H, s). Physical properties: oil.

[0567]

Working Example 285 5,5-Dimethyl-4-hydroxy-
1-methoxyethoxy-2-oxo-3- (2-chloro-6-fluorophenyl) -2,5-dihydro-1H-
Pyrrole (Compound No. 2-530) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.35-7.15 (2H, m), 7.10-6.9
1 (1H, m), 4.40-4.30 (2H, m), 3.75-3.67 (2H, m),
3.42 (3H, s), 1.55 (6H, s). Physical properties: crystals (melting point: 117-122 ° C).

[0568]

Working Example 286 2,2-Dimethylpropionic Acid = 5,5-dimethyl-1-methoxyethoxy-2-
Oxo-3- (2-chloro-6-fluorophenyl)-
2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 2-531) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.30-7.18 (2H, m), 7.05-6.9
5 (1H, m), 4.35-4.30 (2H, m), 3.75-3.70 (2H, m),
1.53 (3H, s), 1.51 (3H, s), 1.17 (9H, s). Physical properties: oil.

[0569]

Example 287 1-ethoxymethoxy-5,5-dimethyl-4-hydroxy-2-oxo-3- (2-chloro-6-fluorophenyl) -2,5-dihydro-1H-
Pyrrole (Compound No. 2-532) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.35-7.20 (2H, m), 7.10-6.9
5 (1H, m), 5.15 (2H, s), 4.92 (1H, brd.s), 3.95-3.
80 (2H, m), 1.56 (6H, s), 1.28 (3H, t, J = 7.1). Physical properties: oil.

[0570]

Working Example 288 2,2-Dimethylpropionic Acid = 1-ethoxymethoxy-5,5-dimethyl-2-
Oxo-3- (2-chloro-6-fluorophenyl)-
2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 2-533) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.30-7.20 (2H, m), 7.05-6.9
5 (1H, m), 5.12 (2H, s), 3.88 (2H, q, J = 7.0), 1.52
(3H, s), 1.50 (3H, s), 1.29 (3H, t, J = 7.0), 1.18
(9H, s). Physical properties: crystals (melting point: 131-134 ° C).

[0571]

Working Example 289 Cyclopropanecarboxylic acid = 5,5-dimethyl-1-methoxymethoxy-2-
Oxo-3- (2,3,6-trimethylphenyl)-
2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 2-534) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.01 (1H, d, J = 7.7), 6.93
(1H, d, J = 8.0), 5.06 (2H, s), 3.62 (3H, s), 2.23
(3H, s), 2.15 (3H, s), 2.09 (3H, s), 1.52 (6H, s),
1.70-1.50 (1H, m), 0.88-0.76 (4H, m). Physical properties: crystals (melting point: 117-118 ° C).

[0572]

Example 290 5,5-Dimethyl-4-hydroxy-
1-methoxymethoxy-2-oxo-3- (2-methyl-6-ethylphenyl) -2,5-dihydro-1H-pyrrole (Compound No. 2-535) ¹ H-NMR (CDCl ₃ ) δ (ppm) : 7.23-7.07 (3H, m), 5.02 (2
H, s), 3.59 (3H, s), 2.49 (2H, q, J = 7.3), 2.17 (3
H, s), 1.53 (6H, s), 1.11 (3H, t, J = 7.3). Physical properties: amorphous.

[0573]

Working Example 291 5,5-Dimethyl-4-hydroxy-
1-methoxyethoxymethoxy-2-oxo-3-
(2,3,4,6-tetramethylphenyl) -2,5-
Dihydro-1H-pyrrole (Compound No. 2-536) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.96 (1H, s), 5.11 (2H, s),
4.00-3.95 (2H, m), 3.70-3.55 (2H, m), 3.39 (3H,
s), 2.27-2.10 (12H, m), 1.53 (3H, s), 1.52 (3H,
s). Physical properties: amorphous.

[0574]

Working Example 292 2,2-Dimethylpropionic acid = 5,5-dimethyl-1-methoxyethoxymethoxy-2-oxo-3- (2,3,4,6-tetramethylphenyl) -2,5 -Dihydro-1H-pyrrole-4-
Il = ester (Compound No. 2-537) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.82 (1H, s), 5.14 (2H, s),
4.03-3.97 (2H, m), 3.64-3.59 (2H, m), 3.40 (3H,
s), 2.21 (3H, s), 2.11 (6H, s), 2.10 (3H, s), 1.56
(6H, s), 1.06 (9H, s). Physical properties: amorphous.

[0575]

Working Example 293 5,5-Dimethyl-4-hydroxy-
1-methoxymethoxy-2-oxo-3- (2,6-dimethyl-6-tert-butylphenyl) -2,5-dihydro-1H-pyrrole (Compound No. 2-538) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.09 (2H, s), 5.01 (2H, s),
3.59 (3H, s), 2.17 (6H, s), 1.52 (6H, s), 1.29 (9
H, s). Physical properties: crystals (melting point: 72-76 ° C).

[0576]

Working Example 294 5,5-Dimethyl-4-hydroxy-
1-methoxymethoxy-2-oxo-3- (2,6-dimethyl-6-methoxyphenyl) -2,5-dihydro-
1H-pyrrole (Compound No. 2-539) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.64 (2H, s), 5.02 (2H, s),
3.78 (3H, s), 3.60 (3H, s), 2.16 (6H, s), 1.52 (6
H, s). Physical properties: crystals (melting point: 154-157 ° C).

[0577]

Example 295 1-ethoxymethoxy-5,5-dimethyl-4-hydroxy-2-oxo-3- (2,6-dimethyl-6-methoxyphenyl) -2,5-dihydro-
1H-pyrrole (Compound No. 2-540) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.61 (2H, s), 6.46 (1H, br)
ds), 5.05 (2H, s), 3.84 (2H, q, J = 7.0), 3.76 (3H,
s), 2.14 (6H, s), 1.51 (6H, s), 1.29 (3H, t, J = 7.
0). Physical properties: Crystal (melting point: 149-151 ° C).

[0578]

Example 296 5,5-Dimethyl-4-hydroxy-
1-methoxymethoxy-2-oxo-3- (2,6-dimethyl-6-phenoxyphenyl) -2,5-dihydro-1H-pyrrole (Compound No. 2-541) ¹ H-NMR (CDCl ₃ ) δ ( ppm): 7.37-7.31 (2H, m), 7.14-7.0
9 (1H, m), 7.03-7.00 (2H, m), 6.70 (2H, s), 6.53
(1H, brd.s), 4.99 (2H, s), 3.58 (3H, s), 2.12 (6H,
s), 1.51 (6H, s). Physical properties: crystals (melting point: 154-158 ° C).

[0579]

Example 297 5,5-Dimethyl-4-hydroxy-
1-Propyl-2-oxo-3- (2,6-dimethylphenyl) -2,5-dihydro-1H-pyrrole (Compound No. 2-542) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.11- 6.99 (3H, m), 4.01 (2
(H, t, J = 6.8), 2.12 (6H, s), 1.76-1.68 (2H, m), 1.45
(6H, s), 0.99 (3H, t, J = 7.1). Physical properties: crystals (melting point: 145-146 ° C).

[0580]

Working Example 298 1-Isopropyl-5,5-dimethyl-4-hydroxy-2-oxo-3- (2,6-dimethylphenyl) -2,5-dihydro-1H-pyrrole (Compound No. 2-543) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.15-7.04 (3H, m), 4.30-4.2
5 (1H, m), 2.16 (6H, s), 1.48 (6H, s), 1.32 (6H,
d, J = 6.4). Physical properties: crystals (melting point: 176-178 ° C).

[0581]

Working Example 299 1-Cyclopropylmethyl-5,5-
Dimethyl-4-hydroxy-2-oxo-3- (2,6
-Dimethylphenyl) -2,5-dihydro-1H-pyrrole (Compound No. 2-544) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.19-7.05 (3H, m), 6.30 (1
H, s), 3.93 (2H, d, J = 7.1), 2.18 (6H, s), 1.52 (6
H, s), 1.40-1.18 (1H, m), 0.65-0.58 (2H, m), 0.37-
0.30 (2H, m). Physical properties: crystals (melting point: 137-140 ° C).

[0582]

Example 300 5,5-Dimethyl-4-hydroxy-
1- (2-propyne) -2-oxo-3- (2,6-dimethylphenyl) -2,5-dihydro-1H-pyrrole (Compound No. 2-545) ¹ H-NMR (CDCl ₃ ) δ (ppm) ): 7.08-6.96 (3H, m), 4.61 (2
H, d, J = 2.6), 2.52 (1H, t, J = 2.6), 2.07 (6H, s), 1.
43 (6H, s). Physical properties: crystals (melting point: 158-160 ° C).

[0583]

Working Example 301 5,5-Dimethyl-4-hydroxy-
1-methylthiomethyl-2-oxo-3- (2,6-dimethylphenyl) -2,5-dihydro-1H-pyrrole (Compound No. 2-546) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.18 -7.06 (3H, m), 5.15 (2
H, s), 2.35 (3H, s), 2.18 (6H, s), 1.54 (6H, s). Physical properties: crystals (melting point: 119-120 ° C).

[0584]

Working Example 302 2,2-Dimethylpropionic Acid = 5,5-dimethyl-1-methylthiomethyl-2-
Oxo-3- (2,6-dimethylphenyl) -2,5-
Dihydro-1H-pyrrol-4-yl ester (Compound No. 2-547) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.15-6.98 (3H, m), 5.20 (2
H, s), 2.37 (3H, s), 2.20 (6H, s), 1.52 (6H, s),
1.06 (9H, s). Physical properties: oil.

[0585]

Working Example 303 1-Ethoxyethyl-5,5-dimethyl-4-hydroxy-2-oxo-3- (2,6-dimethylphenyl) -2,5-dihydro-1H-pyrrole (Compound No. 2-548) ) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.20-7.04 (3H, m), 4.26-4.2
0 (2H, m), 3.75-3.69 (2H, m), 3.57 (2H, q, J = 7.0),
2.17 (6H, s), 1.52 (6H, s), 1.23 (3H, t, J = 7.0). Physical properties: amorphous.

[0586]

Working Example 304 2,2-Dimethylpropionic Acid = 1-ethoxyethyl-5,5-dimethyl-2-oxo-3- (2,6-dimethylphenyl) -2,5-dihydro-1H-pyrrole -4-yl = ester (Compound No. 2-549) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.11-6.97 (3H, s), 4.34-4.2
8 (2H, s), 3.78-3.72 (2H, s), 3.59 (2H, q, J = 7.3),
2.20 (6H, s), 1.50 (6H, s), 1.05 (9H, s). Physical properties: oil.

[0587]

Working Example 305 5,5-Dimethyl-4-hydroxy-
1-methoxyethoxymethyl-2-oxo-3- (2,
6-dimethylphenyl) -2,5-dihydro-1H-pyrrole (compound number 2-550) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.26-7.08 (3H, m), 6.37 (1
H, brd.s), 5.12 (2H, s), 4.02-3.96 (2H, m), 3.65-
3.60 (2H, m), 3.41 (3H, s), 2.19 (6H, s), 1.54 (6H,
s). Physical properties: amorphous.

[0588]

Working Example 306 2,2-Dimethylpropionic acid = 5,5-dimethyl-1-methoxyethoxymethyl-2-oxo-3- (2,6-dimethylphenyl)-
2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 2-551) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.14-6.98 (3H, m), 5.15 (2
H, s), 4.03-3.98 (2H, m), 3.65-3.59 (2H, m), 3.40
(3H, s), 2.19 (6H, s), 1.50 (6H, s), 1.06 (9H,
s). Physical properties: amorphous.

[0589]

Working Example 307 5,5-Dimethyl-4-hydroxy-
1- (2,2-dimethoxyethyl) -2-oxo-3-
(2,6-dimethylphenyl) -2,5-dihydro-1
H-pyrrole (Compound No. 2-552) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.21-7.05 (3H, m), 4.77 (1
H, t, J = 5.1), 4.10 (2H, d, J = 5.1), 3.45 (6H, s), 2.
17 (6H, s), 1.52 (6H, s). Physical properties: amorphous.

[0590]

Working Example 308 2,2-Dimethylpropionic reed
Dd = 5,5-dimethyl-1- (2,2-dimethoxyethyl)
Tyl) -2-oxo-3- (2,6-dimethylphenyi
) -2,5-dihydro-1H-pyrrol-4-yl =
Ester (Compound No. 2-553) ¹ H-NMR (CDCl_Three) δ (ppm): 7.14-6.98 (3H, m), 4.79 (1
H, t, J = 5.1), 4.15 (2H, d, J = 5.1), 3.47 (6H, s), 2.
19 (6H, s), 1.50 (6H, s), 1.05 (9H, s). Physical properties: amorphous.

[0591]

Working Example 309 5,5-Dimethyl-4-hydroxy-
1- (3-methoxypropyl) -2-oxo-3-
(2,6-dimethylphenyl) -2,5-dihydro-1
H-pyrrole (Compound No. 2-554) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.16-7.04 (3H, m), 6.61 (1
H, brd.s), 4.17 (2H, t, J = 6.0), 3.56 (2H, t, J = 6.
0), 3.34 (3H, s), 2.17 (6H, s), 1.98 (2H, tt, J = 6.
0, 6.0), 1.50 (6H, s). Physical properties: Crystal (melting point: 97-100 ° C).

[0592]

Example 310 5,5-Dimethyl-4-hydroxy-
1- (2-methoxy-1-methylethyl) -2-oxo-3- (2,6-dimethylphenyl) -2,5-dihydro-1H-pyrrole (Compound No. 2-555) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.06-6.94 (3H, m), 4.13-4.0
4 (1H, m), 3.53-3.47 (1H, m), 3.45-3.33 (1H, m),
3.31 (3H, s), 2.07 (6H, s), 1.39 (6H, s), 1.27 (3
H, d, J = 6.6). Physical properties: amorphous.

[0593]

Example 311 5,5-Dimethyl-4-hydroxy-
1- (tetrahydrofuran-3-ylmethyl) -2-oxo-3- (2,6-dimethylphenyl) -2,5-dihydro-1H-pyrrole (Compound No. 2-556) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.20-7.02 (3H, m), 4.08-4.0
0 (2H, s), 3.90-3.61 (2H, m), 3.60-3.55 (2H, m),
2.77-2.60 (1H, m), 2.15 (6H, s), 2.16-2.00 (1H,
m), 1.78-1.53 (2H, m), 1.47 (6H, s). Physical properties: oil.

[0594]

Example 312 5,5-Dimethyl-4-hydroxy-
1- (tetrahydrofuran-3-yl) -2-oxo-
3- (2,6-Dimethylphenyl) -2,5-dihydro-1H-pyrrole (Compound No. 2-557) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.17-7.02 (3H, m), 4.86 -4.8
2 (1H, m), 4.09-4.05 (1H, m), 4.02-3.94 (1H, m),
3.83-3.73 (2H, m), 2.37-2.30 (1H, m), 2.15 (6H,
s), 2.05-1.94 (1H, m), 1.49 (3H, s), 1.48 (3H,
s). Physical properties: crystals (melting point: 142-147 ° C).

[0595]

Example 313 4-Hydroxy-1-methoxymethoxy
C-3- (2,4-dichlorophenyl) -1-azaspire
B [4.5] decane-3-en-2-one (compound number
3-8) ¹ H-NMR (CDCl_Three) δ (ppm): 7.44 (1H, d, J = 1.8), 7.29-7.
24 (1H, m), 7.07 (1H, d, J = 8.4), 5.10 (2H, d, J = 1.
1), 4.57 (1H, s), 3.63 (3H, s), 2.10-1.60 (10H,
m). Physical properties: crystals (melting point: 161-163 ° C).

[0596]

Working Example 314 4-Hydroxy-1-methoxymethoxy-3- (2,6-dimethylphenyl) -1-azaspiro [4,5] decane-3-en-2-one (Compound No. 3-104) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.27-7.10 (3H, m), 5.04 (2
H, s), 3.61 (3H, s), 2.36-1.57 (16H, m). Physical properties: crystals (melting point: 170-172 ° C).

[0597]

Working Example 315 4-Hydroxy-1-methoxymethoxy-3- (2-methyl-6-chlorophenyl) -1-azaspiro [4,5] decane-3-en-2-one (Compound No. 3-136) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.22-7.18 (3H, m), 6.31 (1
H, s), 5.05 (2H, s), 3.62 (3H, s), 2.26 (3H, s),
2.11-1.26 (10H, m). Physical properties: crystals (melting point: 172-174 ° C).

[0598]

Example 316 4-Hydroxy-1-methoxymethoxy-3- (2,3,4,6-tetramethylphenyl)-
1-Azaspiro [4,5] decane-3-en-2-one (Compound No. 3-248) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.92 (1H, s), 6.30 (1H, br)
ds), 5.04 (2H, s), 3.61 (3H, s), 2.28-1.29 (22H,
m). Physical properties: Crystal (melting point: 170-171 ° C).

[0599]

Working Example 317 4-Hydroxy-1-methoxymethoxy-3- (2,3,6-trimethylphenyl) -1-azaspiro [4,5] decane-3-en-2-one (Compound No. 3-232) ) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.08-6.96 (2H, m), 5.03 (2
H, s), 3.61 (3H, s), 2.31-1.68 (19H, m). Physical properties: amorphous.

[0600]

Working Example 318 3- (2,4-Dichlorophenyl)-
4-Hydroxy-1-methoxymethoxy-1-azaspiro [4,5] decane-3-en-2-one (Compound No. 3-281) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.42-7.23 ( 3H, m), 5.12 (2
H, s), 3.63 (3H, s), 2.15-1.26 (10H, m). Physical properties: crystal (melting point: 173-174 ° C).

[0601]

Working Example 319 4-Hydroxy-1-methoxymethoxy-3- (2,4,6-trimethylphenyl) -1-azaspiro [4.5] decane-3-en-2-one (Compound No. 3-390) ) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.90 (2H, s), 6.06 (1H, brd.)
s), 5.02 (2H, s), 3.60 (3H, s), 2.27 (3H, s), 2.13
(6H, s), 2.30-1.50 (10H, m). Physical properties: Crystal (melting point: 159-161 ° C).

[0602]

Example 320 4- (2,2-Dimethylpropionyloxy) -1-methoxymethoxy-3- (2,4,6-
Trimethylphenyl) -1-azaspiro [4.5] decane-3-en-2-one (Compound No. 3-391) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.81 (2H, s), 5.08 ( 2H, s),
3.62 (3H, s), 2.23 (3H, s), 2.15 (6H, s), 2.30-1.
55 (10H, m) 1.01 (9H, s). Physical properties: crystals (melting point: 143-145 ° C).

[0603]

Example 321 Cyclopropanecarboxylic acid = 3- (2,4-dichlorophenyl) -1-methoxymethoxy-1-azaspiro [4,5] decane-3-en-2-one-4-yl = ester (Compound No. 3-5
40) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.42-7.40 (1H, m), 7.29-7.2
7 (2H, m), 5.06 (2H, s), 3.63 (3H, s), 2.20-0.95
(15H, m). Physical properties: oil.

[0604]

Working Example 322 3- (2,4-Dichlorophenyl)-
1,8-Dimethoxy-4-hydroxy-1-azaspiro [4,5] decane-3-en-2-one (Compound No. 4
-2) ¹ H-NMR (DMSO-d ₆ ) δ (ppm): 11.85 (1H, s), 7.64
(1H, d, J = 2.2), 7.42 (1H, dd, J = 8.4, 2.2), 7.27
(1H, d, J = 8.4), 3.81 (3H, s), 3.26 (3H, s), 3.48-
3.30 (1H, m), 2.09-1.68 (8H, m). Physical properties: amorphous.

[0605]

Working Example 323 3- (2,4-Dichlorophenyl)-
4-Hydroxy-8-methoxy-1-methoxymethoxy-1-azaspiro [4,5] decane-3-en-2-one (Compound No. 4-8) ¹ H-NMR (DMSO-d ₆ ) δ (ppm ): 11.99 (1H, s), 7.65 (1H,
d, J = 2.2), 7.43 (1H, dd, J = 8.4, 2.1), 7.28 (1H, d,
J = 8.4), 4.90 (2H, s), 3.48 (3H, s), 3.26 (3H, s),
3.49-3.33 (1H, m), 2.08-1.70 (8H, m). Physical properties: amorphous.

[0606]

Working Example 324 1-Ethoxymethoxy-3- (2,4
-Dichlorophenyl) -4-hydroxy-8-methoxy-1-azaspiro [4,5] decane-3-en-2-one (Compound No. 4-11) ¹ H-NMR (DMSO-d ₆ ) δ (ppm) : 11.96 (1H, s), 7.65 (1H,
d, J = 1.8), 7.53 (1H, dd, J = 8.4, 1.8), 7.28 (1H, d,
J = 8.4), 4.94 (2H, s), 3.75 (2H, q, J = 6.9), 3.41-3.
24 (1H, m), 3.26 (3H, s), 2.11-1.70 (8H, m), 1.17
(3H, t, J = 6.9). Physical properties: amorphous.

[0607]

Working Example 325 1,8-Dimethoxy-3- (2,6-
Dimethylphenyl) -4-hydroxy-1-azaspiro
[4,5] decane-3-en-2-one (Compound No. 4
−98) ¹ H-NMR (DMSO-d₆) δ (ppm): 11.40 (1H, s), 7.18-7.03
(3H, m), 3.81 (3H, s), 3.48-3.30 (1H, m), 3.26 (3
H, s), 2.08 (6H, s), 2.07-1.72 (8H, m). Physical properties: Crystal (melting point: 178.0-178.5 ° C).

[0608]

Working Example 326 3- (2,6-Dimethylphenyl)-
4-Hydroxy-8-methoxy-1-methoxymethoxy-1-azaspiro [4,5] decane-3-en-2-one (Compound No. 4-104) ¹ H-NMR (CDCl ₃ ) δ (ppm): 11.52 (1H, s), 7.15-7.03 (3
H, m), 4.90 (2H, s), 3.48 (3H, s), 3.45-3.20 (1H,
m), 3.26 (3H, s), 2.18-1.70 (14H, m). Physical properties: Crystal (melting point: 109-111 ° C).

[0609]

Working Example 327 1-Ethoxymethoxy-3- (2,6
-Dimethylphenyl) -4-hydroxy-8-methoxy-1-azaspiro [4,5] decane-3-en-2-one (Compound No. 4-107) ¹ H-NMR (CDCl ₃ ) δ (ppm): 9.06 (1H, brd.s), 7.18-7.03
(3H, m), 5.05 (2H, s), 3.82 (2H, q, J = 7.0), 3.23-3.
10 (1H, m), 2.63 (3H, s), 2.17 (6H, s), 2.20-1.62
(8H, m), 1.27 (3H, t, J = 7.0). Physical properties: crystals (melting point: 132-137 ° C).

[0610]

Working Example 328 Cyclopropanecarboxylic acid = 3- (2,4-dichlorophenyl) -8-methoxy-1-methoxymethoxy-1-azaspiro [4,5]
Decane-3-en-2-one-4-yl ester (Compound No. 4-399) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.40 (1H, d, J = 1.1), 7.28
(2H, d, J = 1.1), 5.06 (2H, s), 3.63 (3H, s), 3.40
(3H, s), 3.38-3.28 (1H, m), 2.77-1.66 (9H, m). Physical properties: oil.

[0611]

Example 329 Cyclopropanecarboxylic acid = 3- (2,4-dichlorophenyl) -1,8-dimethoxy-1-azaspiro [4,5] decane-3-en-2-one-4-yl = Ester (Compound No. 4-40
0) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.40 (1H, d, J = 1.8), 7.28
(2H, d, J = 1.8), 4.00 (3H, s), 3.49-3.40 (1H, m),
3.40 (3H, s), 2.25-1.68 (9H, m), 1.05-0.94 (4H,
m). Physical properties: oil.

[0612]

Working Example 330 2-Methoxybenzoic Acid =
1-ethoxymethyl-3- (2,6-dimethylphenyl) -8-methoxy-1-azaspiro [4,5] decane-3-en-2-one-4-yl ester (Compound No. 4-401) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.48-7.43 (2H, m), 7.07-6.8
9 (5H, m), 5.16 (2H, s), 3.92 (2H, q, J = 6.9), 3.82
(3H, s), 3.33 (3H, s), 3.30-3.23 (1H, m), 2.25-1.
81 (14H, m), 1.30 (3H, t, J = 6.9). Physical properties: oil.

[0613]

Working Example 331 2-Methylbenzoic acid = 1
-Ethoxymethyl-3- (2,6-dimethylphenyl)
-8-Methoxy-1-azaspiro [4,5] decane-3
-En-2-one-4-yl = ester (Compound No. 4
−402) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.81 (1H, dd, J = 8.1, 1.4),
7.40 (1H, dd, J = 7.7, 1.4), 7.23-7.15 (2H, m), 7.09
-6.93 (3H, m), 5.17 (2H, s), 3.90 (2H, q, J = 6.9),
3.34 (3H, s), 3.41-3.28 (1H, m), 2.31-1.72 (14H,
m), 1.30 (3H, t, J = 6.9). Physical properties: oil.

[0614]

Working Example 332 Cyclopropanecarboxylic acid = 3- (2,6-dimethylphenyl) -1,8-dimethoxy-1-azaspiro [4,5] decane-3-en-2-one-4-yl = Ester (compound number 4-40)
3) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.15-6.99 (3H, m), 4.01 (3H,
s), 3.47-3.36 (1H, m), 3.39 (3H, s), 2.19 (6H,
s), 2.18-1.50 (9H, m), 0.88-0.72 (4H, m). Physical properties: crystals (melting point: 130-133 ° C).

[0615]

Working Example 333 1-Methylcyclopropanecarboxylic acid = 3- (2,6-dimethylphenyl)-
1,8-Dimethoxy-1-azaspiro [4,5] decane-3-en-2-one-4-yl ester (Compound No. 4-404) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.16 -6.99 (3H, m), 4.01 (3H,
s), 3.47-3.35 (1H, m), 3.38 (3H, s), 2.19 (6H,
s), 2.15-1.68 (8H, m), 1.22 (3H, s), 1.03-0.98 (2H,
m), 0.67-0.61 (2H, m). Physical properties: Crystal (melting point: 125-130 ° C).

[0616]

Example 334 Cyclopropanecarboxylic acid = 3- (2,6-dimethylphenyl) -8-methoxy-1-methoxymethoxy-1-azaspiro [4,5]
Decane-3-en-2-one-4-yl ester (Compound No. 4-405) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.15-7.00 (3H, m), 5.08 (2H,
s), 3.62 (3H, s), 3.40 (3H, s), 3.39-3.25 (1H,
m), 2.25-1.50 (15H, m), 0.88-0.72 (4H, m). Physical properties: Crystal (melting point: 89-90 ° C).

[0617]

Working Example 335 1-Methylcyclopropane carboxy
Thick acid = 3- (2,6-dimethylphenyl)-
8-methoxy-1-methoxymethoxy-1-azaspiro
[4,5] decane-3-en-2-one-4-yl = d
Stele (Compound No. 4-406) ¹ H-NMR (CDCl_Three) δ (ppm): 7.15-7.00 (3H, m), 5.07 (2H,
 s), 3.63, 3.62 (3H, s, s), 3.55-3.45 (0.4H, m),
3.39, 3.36 (3H, s, s), 3.37-3.25 (0.6H, m), 2.55-
1.60 (14H, m), 1.22, 1.21 (3H, s, s), 1.01-0.90 (2
H, m), 0.67-0.60 (2H, m). Physical properties: crystals (melting point: 79-84 ° C).

[0618]

Example 336 Cyclopropanecarboxylic acid = 1-ethoxymethyl-3- (2,6-dimethylphenyl) -8-methoxy-1-azaspiro [4,5] decane-3-en-2-one-4 -Yl = ester (Compound No. 4-407) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.15-6.99 (3H, m), 5.13 (2H,
s), 3.87 (2H, q, J = 7.0), 3.40 (3H, s), 3.39-3.23
(1H, m), 2.27-1.55 (15H, m), 1.28 (3H, t, J = 7.0),
0.88-0.74 (4H, m). Physical properties: oil.

[0619]

Working Example 337 1-Methylcyclopropanecarboxylic acid = 1-ethoxymethyl-3- (2,6-
Dimethylphenyl) -8-methoxy-1-azaspiro [4,5] decane-3-en-2-one-4-yl ester (Compound No. 4-408) ¹ H-NMR (CDCl ₃ ) δ (ppm) ： 7.16-6.99 (3H, s), 5.13 (2H,
s), 3.87 (2H, q, J = 7.0), 3.39 (3H, s), 3.36-3.23
(1H, m), 2.26-1.55 (14H, m), 1.29 (3H, t, J = 7.0),
1.23 (3H, s), 1.02-0.96 (2H, m), 0.67-0.61 (2H,
m). Physical properties: crystals (melting point: 105-107 ° C).

[0620]

Working Example 338 Acetic acid = 1-ethoxymethyl-3- (2,6-dimethylphenyl) -8-methoxy-1-azaspiro [4,5] decane-3-en-2
-On-4-yl ester (Compound No. 4-410) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.16-7.00 (3H, m), 5.13 (2H,
s), 3.87 (2H, q, J = 7.0), 3.39 (3H, s), 3.40-3.23
(1H, m), 2.30-1.60 (8H, m), 2.20 (6H, s), 2.01 (3
H, s), 1.29 (3H, t, J = 7.0). Physical properties: Crystal (melting point: 74-75 ° C).

[0621]

Working Example 339 Propionic Acid 1-ethoxymethyl-3- (2,6-dimethylphenyl) -8-methoxy-1-azaspiro [4,5] decane-3-ene-
2-one-4-yl ester (Compound No. 4-41
1) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.16-7.00 (3H, m), 5.13 (2H,
s), 3.94 (2H, q, J = 7.0), 3.88 (2H, q, J = 7.0), 3.3
8 (3H, s), 3.35-3.25 (1H, m), 2.26-1.68 (8H, m), 2.
20 (6H, s), 1.28 (3H, t, J = 7.0), 1.01 (3H, t, J = 7.
0). Physical properties: oil.

[0622]

Working Example 340 3- (2,6-Dimethylphenyl)-
4-hydroxy-8-methoxy-1-methoxyethyl-
1-azaspiro [4,5] decane-3-en-2-one (Compound No. 4-414) One stereoisomer: ¹ H-NMR (DMSO-d ₆ ) δ (ppm): 11.42 (1H, brd) .s), 7.17-7.
02 (3H, m), 4.15-4.10 (2H, m), 3.58-3.53 (2H, m),
3.40-3.30 (1H, m), 3.28 (3H, s), 3.25 (3H, s), 2.1
6-1.75 (8H, m), 2.07 (6H, s). Physical properties: oil. The other stereoisomer: ¹ H-NMR (DMSO-d ₆ ) δ (ppm): 7.14-7.00 (3H, m), 4.15-4.
10 (2H, m), 3.58-3.54 (2H, m), 3.35-3.25 (1H, m),
3.27 (3H, s), 3.26 (3H, s), 21.5-1.75 (8H, m), 2.0
7 (6H, s). Physical properties: crystals (melting point: 161-165 ° C).

[0623]

Working Example 341 Acetic Acid = 3- (2,6
-Dimethylphenyl) -8-methoxy-1-methoxyethyl-1-azaspiro [4,5] decane-3-ene-2
-On-4-yl ester (Compound No. 4-415) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.16-7.00 (3H, m), 4.36-4.31
(2H, m), 3.75-3.67 (2H, m), 3.43, 3.42 (0.75H, 2.
25H, s, s), 3.45-3.35 (1H, m), 3.38 (3H, s), 2.35-
1.65 (8H, m), 2.19 (6H, s), 2.00, 1.99 (2.25H, 0.7
5H, s, s). Physical properties: oil.

[0624]

EXAMPLE 342 Propionic acid = 3- (2,
6-dimethylphenyl) -8-methoxy-1-methoxyethyl-1-azaspiro [4,5] decane-3-ene-
2-one-4-yl ester (Compound No. 4-41
6) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.16-6.99 (3H, m), 4.36-4.31
(2H, m), 3.96, 3.95 (0.5H, 1.5H, q, q, J = 7.0, 7.
0), 3.75-3.67 (2H, m), 3.45-3.35 (1H, m), 3.43, 3.
42 (0.75H, 2.25H, s, s), 3.37 (3H, s), 2.35-1.75
(8H, m), 2.20 (6H, s), 1.03, 1.02 (2.25H, 0.75H, t,
t, J = 7.0, 7.0). Physical properties: oil.

[0625]

Example 343 Cyclopropanecarboxylic acid = 3- (2,6-dimethylphenyl) -8-methoxy-1-methoxyethyl-1-azaspiro [4,5] decane-3-en-2-one-4 -Yl = ester (Compound No. 4-418) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.15-6.99 (3H, m), 4.36-4.31
(2H, m), 3.75-3.67 (2H, m), 3.45-3.35 (1H, m), 3.
43, 3.42 (0.75H, 2.25H, s, s), 3.39 (3H, s), 2.35-
1.70 (8H, m), 1.70-1.50 (1H, m), 0.88-0.70 (4H,
m). Physical properties: oil.

[0626]

Example 344 5,5-Dimethyl-4-hydroxy-
1-methylthio-2-oxo-3- (2,4,6-trimethylphenyl) -2,5-dihydro-1H-pyrrole (Compound No. 5-1) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.92 (2H, s), 6.20 (1H, brd.
s), 2.44 (3H, s), 2.28 (3H, s), 2.13 (6H, s), 1.49
(6H, s). Physical properties: crystals (melting point: 203-204 ° C).

[0627]

Example 345: Methyl carbonate = 5,5-dimethyl-1-methylthio-2-oxo-3- (2,4
6-trimethylphenyl) -2,5-dihydro-1H-
Pyrrole-4-yl ester (Compound No. 5-16) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.86 (2H, s), 3.60 (3H, s),
2.48 (3H, s), 2.26 (3H, s), 2.15 (6H, s), 1.05 (6
H, s). Physical properties: oil.

[0628]

Working Example 346 Dithiocarbonic acid = S-ethyl ester =
O- [5,5-dimethyl-1-methylthio-2-oxo-3- (2,4,6-trimethylphenyl) -2,5-
Dihydro-1H-pyrrol-4-yl] ester (Compound No. 5-39) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.80 (2H, s), 2.98 (2H, q, J
= 7.3), 2.48 (3H, s), 2.23 (3H, s), 2.15 (6H, s),
1.53 (6H, s), 1.16 (3H, t, J = 7.3). Physical properties: oil.

[0629]

Working Example 347 4-Hydroxy-8-methoxy-1-
Methylthio-3- (2,4,6-trimethylphenyl)
-1-azaspiro [4.5] decane-3-en-2-one (compound number 5-67) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.92 (2H, s), 6.03 (1H, brd) .
s), 3.55-3.45 (1H, m), 3.39 (3H, s), 2.41 (3H, s),
2.28 (3H, s), 2.13 (6H, s), 2.56-2.00 (4H, m), 1.82
-1.62 (2H, m), 1.58-1.12 (2H, m). Physical properties: crystals (melting point: 193-196 ° C).

[0630]

Working Example 348 Dithiocarbonate = S-ethyl ester =
O- [8-methoxy-1-methylthio-2-oxo-3
-(2,4,6-trimethylphenyl) -1-azaspiro [4.5] decane-3-en-4-yl] ester (Compound No. 5-68) ¹ H-NMR (CDCl ₃ ) δ (ppm) : 6.82 (2H, s), 3.49-3.26 (4H,
m), 2.56-1.50 (17H, m), 1.02 (4H, s), 0.99 (5H,
s). Physical properties: amorphous.

[0631]

Working Example 349 2,2-Dimethylpropionic Acid = [8-methoxy-1-methylthio-2-oxo-
3- (2,4,6-trimethylphenyl) -1-azaspiro [4.5] decane-3-en-4-yl] ester (Compound No. 5-70) ¹ H-NMR (CDCl ₃ ) δ (ppm) ): 6.80 (2H, s), 3.53-3.29 (1H,
m), 3.02-2.90 (2H, m), 2.46, 2.45 (3H, s, s), 2.2
2 (3H, s), 2.15 (6H, s), 2.60-1.50 (8H, m), 1.16-1.
07 (3H, m). Physical properties: amorphous.

[0632]

Example 350 3,3-Dimethylbutyric acid = 5,5-dimethyl-1-ethylthio-2-oxo-3
-(2,4,6-trimethylphenyl) -2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 5-93) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.82 (2H , s), 2.88 (2H, q, J
= 7.3), 2.23 (3H, s), 2.18 (2H, s), 2.13 (6H, s),
1.45 (6H, s), 1.28 (3H, t, J = 7.3), 0.83 (9H, s). Physical properties: crystal (melting point: 77-81 ° C).

[0633]

Working Example 351 1,2-isobutyl carbonate = 5,5-dimethyl-1-ethylthio-2-oxo-3
-(2,4,6-trimethylphenyl) -2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 5-99) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.84 (2H , s), 3.74 (2H, d, J
= 6.6), 2.88 (2H, q, J = 7.3), 2.25 (3H, s), 2.15 (6
H, s), 1.76 (1H, septet, J = 6.6), 1.50 (6H, s), 1.2
8 (3H, t, J = 7.3), 0.77 (6H, d, J = 6.6). Physical properties: oil.

[0634]

Working Example 352 Carbonic acid = cyclopentyl = ester =
5,5-dimethyl-1-ethylthio-2-oxo-3-
(2,4,6-trimethylphenyl) -2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 5-101) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.85 (2H, s), 4.84-4.80 (1H,
m), 2.88 (2H, q, J = 7.3), 2.25 (3H, s), 2.15 (6H,
s), 1.69-1.35 (8H, m), 1.28 (3H, t, J = 7.3). Physical properties: oil.

[0635]

Working Example 353 Carbonic acid = 3,3-dimethylbutyl ester = 5,5-dimethyl-1-ethylthio-2-oxo-3- (2,4,6-trimethylphenyl) -2,5-
Dihydro-1H-pyrrol-4-yl ester (Compound No. 5-104) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.83 (2H, s), 3.67 (2H, s),
2.89 (2H, q, J = 7.3), 2.24 (3H, s), 2.15 (6H, s),
1.50 (6H, s), 1.28 (3H, t, J = 7.3), 0.77 (9H, s). Physical properties: oil.

[0636]

Working Example 354 Tetrahydrofuran-2-yl Carbonate
Methyl ester = 5,5-dimethyl-1-ethylthio
-2-oxo-3- (2,4,6-trimethylphenyi
) -2,5-dihydro-1H-pyrrol-4-yl =
Ester (Compound No. 5-105) ¹ H-NMR (CDCl_Three) δ (ppm): 6.85 (2H, s), 4.02-3.88 (3H,
 m), 3.80-3.70 (2H, m), 2.88 (2H, q, J = 7.3), 2.25
(3H, s), 2.15 (6H, s), 1.89-1.60 (4H, m), 1.49 (6
H, s), 1.27 (3H, t, J = 7.3). Physical properties: oil.

[0637]

Working Example 355 2-isopropoxyethyl carbonate = ester = 5,5-dimethyl-1-ethylthio-2-oxo-3- (2,4,6-trimethylphenyl) -2,5
-Dihydro-1H-pyrrol-4-yl ester (Compound No. 5-108) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.85 (2H, s), 4.11-4.06 (2H,
m), 3.54-3.39 (3H, m), 2.88 (2H, q, J = 7.3), 2.25
(3H, s), 2.15 (6H, s), 1.50 (6H, s), 1.28 (3H, t,
J = 7.3), 1.11 (6H, d, J = 6.2). Physical properties: oil.

[0638]

Example 356 Carbonic acid = 1,2-dimethylpropyl ester = 5,5-dimethyl-1-ethylthio-2-oxo-3- (2,4,6-trimethylphenyl) -2,5
-Dihydro-1H-pyrrol-4-yl ester (Compound No. 5-109) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.83 (2H, s), 4.23 (1H, m),
2.89 (2H, q, J = 7.3), 2.23 (3H, s), 2.15 (6H, s),
1.65-1.55 (1H, m), 1.50 (6H, s), 1.28 (3H, t, J = 7.
3), 0.97 (3H, d, J = 6.6), 0.74 (6H, dd, J = 7.0, 1.
8). Physical properties: oil.

[0639]

Working Example 357 Carbonic acid = 1,1-dimethylpropane-2
-Inyl = ester = 5,5-dimethyl-1-ethylthio-2-oxo-3- (2,4,6-trimethylphenyl) -2,5-dihydro-1H-pyrrol-4-yl =
Ester (Compound No. 5-110) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.83 (2H, s), 2.88 (2H, q, J
= 7.3), 2.43 (1H, s), 2.23 (3H, s), 2.15 (6H, s),
1.50 (6H, s), 1.42 (6H, s), 1.27 (3H, t, J = 7.3). Physical properties: oil.

[0640]

Working Example 358 Carbonic acid = 1,2,2-trimethylpropyl ester = 5,5-dimethyl-1-ethylthio-2
-Oxo-3- (2,4,6-trimethylphenyl)-
2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 5-111) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.82 (2H, s), 4.28 (1H, q, J
= 6.6), 2.89 (2H, q, J = 7.3), 2.22 (3H, s), 2.15 (6
H, s), 1.50 (6H, s), 1.28 (3H, t, J = 7.3), 0.94 (3
H, d, J = 6.6), 0.751 (9H, s). Physical properties: oil.

[0641]

Example 359 1-isopropyl-2-methylpropyl carbonate = 5,5-dimethyl-1-ethylthio-2-oxo-3- (2,4,6-trimethylphenyl) -2,5-dihydro -1H-pyrrol-4-yl =
Ester (Compound No. 5-112) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.80 (2H, s), 4.14 (1H, t, J
= 6.2), 2.89 (2H, q, J = 7.3), 2.21 (3H, s), 2.15 (6
H, s), 1.89-1.72 (2H, m), 1.58 (6H, s), 1.28 (3H,
t, J = 7.3), 0.67 (12H, m). Physical properties: Crystal (melting point: 89-90 ° C).

[0642]

Example 360 3,3-Dimethylbutenoic acid = 5,5-dimethyl-1-propylthio-2-oxo-3- (2,4,6-trimethylphenyl) -2,5-
Dihydro-1H-pyrrol-4-yl ester (Compound No. 5-164) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.81 (2H, s), 2.82 (2H, t, J)
= 7.7), 2.23 (3H, s), 2.18 (2H, s), 2.13 (6H, s),
1.72-1.58 (2H, m), 1.45 (6H, s), 1.04 (3H, t, J = 7.
7), 0.83 (9H, s). Physical properties: crystals (melting point: 57-58 ° C).

[0643]

Working Example 361 3,3-Dimethylbutyric acid = 5,5-dimethyl-1-isopropylthio-2-oxo-3- (2,4,6-trimethylphenyl) -2,5
-Dihydro-1H-pyrrol-4-yl ester (Compound No. 5-168) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.82 (2H, s), 3.41 (1H, sept)
et, J = 6.6), 2.23 (3H, s), 2.18 (2H, s), 2.14 (6H,
s), 1.45 (6H, s), 1.26 (6H, d, J = 6.6), 0.83 (9H,
s). Physical properties: crystals (melting point: 89-91 ° C).

[0644]

Working Example 362 3,3-Dimethylbutyric acid = 5,5-dimethyl-1-butylthio-2-oxo-3
-(2,4,6-trimethylphenyl) -2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 5-172) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.81 (2H , s), 2.85 (2H, t, J
= 9.5), 2.23 (3H, s), 2.18 (2H, s), 2.13 (6H, s),
1.66-1.45 (4H, m), 1.45 (6H, s), 0.91 (3H, t, J = 7.
3). Physical properties: oil.

[0645]

Working Example 363 3,3-Dimethylbutyric acid = 5,5-dimethyl-1-isobutylthio-2-oxo-3- (2,4,6-trimethylphenyl) -2,5-
Dihydro-1H-pyrrol-4-yl ester (Compound No. 5-176) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.81 (2H, s), 2.73 (2H, d, J)
= 7.0), 2.23 (3H, s), 2.18 (2H, s), 2.13 (6H, s),
1.98-1.82 (1H, m), 1.45 (6H, s), 1.05 (6H, d, J = 6.
6), 0.83 (9H, s). Physical properties: Crystal (melting point: 51-52 ° C).

[0646]

Working Example 364 3,3-Dimethylbutyric acid = 5,5-dimethyl-1-benzylthio-2-oxo-
3- (2,4,6-trimethylphenyl) -2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 5-184) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.33- 7.26 (5H, m), 6.82 (2H,
s), 4.13 (2H, s), 2.24 (3H, s), 2.14 (6H, s), 1.1
8 (6H, s), 0.81 (9H, s). Physical properties: oil.

[0647]

Working Example 365 3,3-Dimethylbutyric quasid = 5,5-dimethyl-1-phenylthio-2-oxo-3- (2,4,6-trimethylphenyl) -2,5-
Dihydro-1H-pyrrol-4-yl ester (Compound No. 5-188) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.41-7.20 (5H, m), 6.82 (2H,
s), 2.25 (3H, s), 2.19 (6H, s), 2.18 (2H, s), 1.3
9 (6H, s), 0.83 (9H, s). Physical properties: Crystal (melting point: 109-111 ° C).

[0648]

Working Example 366 Cyclopropanecarboxylic acid = 5,5-dimethyl-1-methylthio-2-oxo-3- (2,4,6-trimethylphenyl) -2,5-
Dihydro-1H-pyrrol-4-yl ester (Compound No. 5-190) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.84 (2H, s), 2.45 (3H, s),
2.13 (6H, s), 1.67-1.52 (1H, m), 1.47 (6H, s), 0.
92-0.77 (4H, m). Physical properties: Crystal (melting point: 89-92 ° C).

[0649]

Working Example 367 Dithiocarbonic acid = S-ethyl ester =
O- [5,5-dimethyl-1-methylthio-2-oxo-3- (2-chlorophenyl) -2,5-dihydro-1
H-pyrrol-4-yl] ester (compound number 6-
4) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.38-7.19 (4H, m), 3.02 (2H,
q, J = 7.3), 2.50 (3H, s), 1.54 (6H, s), 1.22 (3H,
t, J = 7.3). Physical properties: Crystal (melting point: 89-90 ° C).

[0650]

Working Example 368 Dithiocarbonic acid = S-ethyl ester =
O- [5,5-dimethyl-1-methylthio-2-oxo-3- (2-trifluoromethylphenyl) -2,5-
Dihydro-1H-pyrrol-4-yl] ester (Compound No. 6-8) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.67-7.35 (4H, m), 2.99 (2H,
q, J = 7.3), 2.49 (3H, s), 1.54 (3H, s), 1.50 (3H,
s), 1.21 (3H, t, J = 7.3). Physical properties: oil.

[0651]

Working Example 369 Dithiocarbonic acid = S-ethyl ester =
O- [5,5-dimethyl-1-methylthio-2-oxo-3- (2-chloro-4-methylphenyl) -2,5-
Dihydro-1H-pyrrol-4-yl] ester (Compound No. 6-12) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.22-7.17 (2H, m), 7.10-7.05
(1H, m), 3.04 (2H, q, J = 7.3), 2.49 (3H, s), 2.31 (3
H, s), 1.53 (6H, s), 1.24 (3H, t, J = 7.3). Physical properties: oil.

[0652]

Example 370 Dithiocarbonate = S-ethyl ester =
O- [5,5-dimethyl-1-ethylthio-2-oxo-3- (2-chloro-4-methylphenyl) -2,5-
Dihydro-1H-pyrrol-4-yl] ester (Compound No. 6-16) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.21-7.17 (2H, m), 7.09-7.05
(1H, m), 3.04 (2H, q, J = 7.5), 2.91 (2H, q, J = 7.5),
2.91 (2H, q, J = 7.5), 2.30 (3H, s), 1.52 (6H, s),
1.29 (3H, t, J = 7.3), 1.24 (3H, t, J = 7.5). Physical properties: oil.

[0653]

Working Example 371 Dithiocarbonic acid = S-ethyl ester =
O- [5,5-dimethyl-1-propylthio-2-oxo-3- (2-chloro-4-methylphenyl) -2,5
-Dihydro-1H-pyrrol-4-yl] ester (Compound No. 6-20) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.21-7.17 (2H, m), 7.09-7.04
(1H, m), 3.04 (2H, q, J = 7.5), 2.84 (2H, t, J = 7.3),
2.30 (3H, s), 1.77-1.58 (2H, m), 1.51 (6H, s), 1.2
4 (3H, t, J = 7.5), 1.04 (3H, t, J = 7.3). Physical properties: oil.

[0654]

Working Example 372 2,2-Dimethylpropionic Acid = 5,5-dimethyl-1-ethylthio-2-oxo-3- (2,4-dichlorophenyl) -2,5-dihydro-1H-pyrrole-4 -Ill-ester (Compound No. 6-30) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.40-7.38 (1H, m), 7.29-7.26
(2H, m), 2.89 (2H, q, J = 7.4), 1.45 (6H, s), 1.27
(3H, t, J = 7.4), 1.20 (9H, s). Physical properties: Crystal (melting point: 73-76 ° C).

[0655]

Working Example 373 Dithiocarbonic acid = S-ethyl ester =
O- [5,5-dimethyl-1-methylthio-2-oxo-3- (2-bromo-4-methylphenyl) -2,5-
Dihydro-1H-pyrrol-4-yl] ester (Compound No. 6-36) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.38-7.37 (1H, m), 7.18-7.09
(2H, m), 3.03 (2H, q, J = 7.3), 2.49 (3H, s), 2.30
(3H, s), 1.52 (6H, brd.s), 1.23 (3H, t, J = 7.3). Physical properties: oil.

[0656]

Working Example 374 Dithiocarbonic acid = S-ethyl ester =
O- [5,5-dimethyl-1-methylthio-2-oxo-3- (2-methyl-4-methoxyphenyl) -2,5
-Dihydro-1H-pyrrol-4-yl] ester (Compound No. 6-40) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.07-7.03 (1H, m), 6.72-6.67
(2H, m), 3.77 (3H, s), 3.01 (2H, q, J = 7.7), 2.48
(3H, s), 2.22 (3H, s), 1.51 (6H, s), 1.21 (3H, t,
= 7.7). Physical properties: oil.

[0657]

Working Example 375 Dithiocarbonate = S-ethyl ester =
O- [1-ethylthio-5,5-dimethyl-2-oxo-3- (2-chlorophenyl) -2,5-dihydro-1
H-pyrrol-4-yl] ester (Compound No. 6-4
1) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.38-7.22 (4H, m), 3.02 (2
(H, q, J = 7.3), 2.92 (2H, q, J = 7.3), 1.56 (6H, s), 1.
30 (3H, t, J = 7.3), 1.22 (3H, t, J = 7.3). Physical properties: Crystal (melting point: 97-98 ° C).

[0658]

Working Example 376 2-Chlorobenzoic acid =
5,5-dimethyl-1-methylthio-2-oxo-3-
(2-Chlorophenyl) -2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 6-42) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.86-7.81 (1H, m), 7.52-7.2
5 (7H, m), 2.52 (3H, s), 1.56 (6H, s). Physical properties: oil.

[0659]

Working Example 377 Thiophosphonic Acid = O, O ′
-Diethyl ester = O "-[5,5-dimethyl-1-
Methylthio-2-oxo-3- (2-chlorophenyl)
-2,5-Dihydro-1H-pyrrol-4-yl] ester (Compound No. 6-43) ¹ H-NMR (CDCl ₃ ) δ (ppm): 8.07-8.02 (1H, m), 7.44-7.2
8 (3H, m), 4.26-4.04 (4H, m), 2.08 (3H, s), 1.79
(3H, s), 1.60 (3H, s), 1.28-1.18 (6H, m). Physical properties: oil.

[0660]

Working Example 378 Dithiocarbonic acid = S-ethyl ester =
O- [1-tert-butylthio-5,5-dimethyl-
2-oxo-3- (2-chlorophenyl) -2,5-dihydro-1H-pyrrol-4-yl] ester (compound No. 6-44) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.39-7.21 (4H, m), 3.01 (2
H, q, J = 7.3), 1.60 (6H, s), 1.46 (9H, s), 1.21 (3H,
t, J = 7.3). Physical properties: Crystal (melting point: 99-103 ° C).

[0661]

Example 379 Cyclopropanecarboxylic acid = 5,5-dimethyl-1-methylthio-2-oxo-3- (2,4-dichlorophenyl) -2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 6-45) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.40-7.25 (3H, m), 2.48 (3
H, s), 1.80-1.68 (1H, m), 1.48 (6H, s), 1.05-0.97
(4H, m). Physical properties: oil.

[0662]

Example 380 Cyclopropanecarboxylic acid = 5,5-dimethyl-1-methylthio-2-oxo-3- (2,6-dimethylphenyl) -2,5-dihydro-1H-pyrrol-4-yl = Ester (Compound No. 6-46) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.15-6.98 (3H, m), 2.48 (3
H, s), 2.18 (6H, s), 1.67-1.55 (1H, m), 1.48 (6H,
s), 0.90-0.75 (4H, m). Physical properties: oil.

[0663]

Working Example 381 2- [N-hydroxy-N-[(2,
4-Dichlorophenyl) acetyl] amino-2-methylpropionic acid ethyl ester (Compound No. 8-60) ¹ H-NMR (DMSO-d ₆ ) δ (ppm): 10.06 (1H, s), 7.54 ( 1H,
m), 7.37-7.34 (2H, m), 3.99 (2H, q, J = 7.0), 3.83 (2
H, s), 1.35 (6H, s), 1.12 (3H, t, J = 7.0). Physical properties: crystals (melting point: 115-116 ° C).

[0664]

Working Example 382 2- [N-methoxy-N-[(2,4
-Dichlorophenyl) acetyl] amino-2-methylpropionic acid ethyl ester (Compound No. 8-61) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.38 (1H, m), 7.22-7.21 (2H ,
m), 4.14 (2H, q, J = 7.0), 3.97-3.30 (2H, m), 3.91
(3H, s), 1.65-1.45 (6H, m), 1.22 (3H, t, J = 7.0).

[0665]

Working Example 383 2- [N-hydroxy-N-[(2-
Chloro-4-methylphenyl) acetyl] amino-2-
Methyl propionic acid ethyl ester (Compound No. 8-65) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.19-7.13 (2H, m), 7.03-6.9
9 (1H, m), 6.52 (1H, brd.s), 4.17 (2H, q, J = 7.3),
3.88 (2H, s), 2.32 (3H, s), 1.54 (6H, s), 1.24 (3
H, t, J = 7.3).

[0666]

Working Example 384 N- (1-Cyano-4-methylcyclohexyl) -N-hydroxy-2- (2,4,6-trimethylphenyl) acetamide (Compound No. 9-3) ¹ H-NMR (DMSO-d) ₆ ) δ (ppm): 10.31 (1H, s), 6.81 (2H,
s), 3.74 (2H, s), 2.20 (3H, s), 2.12 (6H, s), 2.50-
2.20 (2H, m), 1.90-1.70 (4H, m), 1.52-1.10 (3H,
m), 0.90 (3H, d, J = 3.3).

[0667]

Working Example 385 N- (1-Cyano-4-methoxycyclohexyl) -N-hydroxy-2- (2,4,6-trimethylphenyl) acetamide (Compound No. 9-4) ¹ H-NMR (DMSOd ₆ ) δ (ppm): 10.36 (1H, s), 6.79 (2H,
s), 3.73 (2H, s), 3.28 (1H, m), 3.22 (3H, s), 2.59
-1.83 (8H, m), 2.18 (3H, s), 2.101 (6H, s). Physical properties: oil.

[0668]

Working Example 386 N- (1-Cyano-4-methylcyclohexyl) -N-methoxy-2- (2,4,6-trimethylphenyl) acetamide (Compound No. 9-11) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.86 (2H, s), 4.09-3.60 (2H,
m), 3.40 (3H, s), 2.51-2.30 (2H, m), 2.25 (3H,
s), 2.22 (6H, s), 2.20-1.70 (4H, m), 1.50-1.33 (3H,
m), 0.94 (3H, d, J = 3.3).

[0669]

Working Example 387 1,4-Bis (methoxymethoxy)-
5,5-dimethyl-3- (2,6-dimethylphenyl)
-2-oxo-2,5-dihydro-1H-pyrrole (Compound No. 10-1) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.0-7.2 (3H, m), 5.03 (2H,
s), 4.69 (2H, s), 3.60 (3H, s), 3.36 (3H, s), 2.18
(6H, s), 1.53 (6H, s). Physical properties: oil.

[0670]

Working Example 388 1,4-Bis (methoxymethoxy)-
5,5-dimethyl-3- (2-methyl-6-chlorophenyl) -2-oxo-2,5-dihydro-1H-pyrrole (Compound No. 10-46) ¹ H-NMR (CDCl ₃ ) δ (ppm) : 7.13-7.23 (3H, m), 5.03 (2
H, s), 4.79 (2H, ABq, J = 5.5), 3.60 (3H, s), 3.38
(3H, s), 2.25 (3H, s), 1.54 (3H, s), 1.52 (3H, s). Physical properties: oil.

[0671]

Working Example 389 5,5-Dimethyl-1,4-bis (methoxymethyl) -2-oxo-3- (2-chloro-6-
(Fluorophenyl) -2,5-dihydro-1H-pyrrole (Compound No. 10-136) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.35-7.18 (2H, m), 7.05-6.9
5 (1H, m), 5.02 (2H, s), 4.89 (2H, s), 3.61 (3H,
s), 3.38 (3H, s), 1.53 (6H, s). Physical properties: oil.

[0672]

Working Example 390 5,5-Dimethyl-1,4-bis (methoxymethyl) -2-oxo-3- (2-bromo-4,
6-dimethylphenyl) -2,5-dihydro-1H-pyrrole (Compound No. 10-137) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.26 (1H, s), 6.98 (1H, s),
5.02 (2H, s), 4.82 (2H, ABq, J = 5.5), 3.59 (3H,
s), 3.39 (3H, s), 2.28 (3H, s), 2.21 (3H, s), 1.54
(3H, s), 1.51 (3H, s). Physical properties: oil.

[0673]

Example 391 Cyclopropanecarboxylic acid = 5,5-dimethyl-1-methoxyethoxy-2-
Oxo-3- (2,3,6-trimethylphenyl)-
2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 10-138) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.00 (1H, d, J = 7.7), 6.91
(1H, d, J = 7.7), 4.33-4.27 (2H, m), 3.73-3.67 (2H,
m), 3.43 (3H, s), 2.22 (3H, s), 2.13 (3H, s), 2.08
(3H, s), 1.65-1.52 (1H, m), 1.52 (6H, s), 0.90-0.7
5 (4H, m). Physical properties: oil.

[0674]

Working Example 392 Cyclopropanecarboxylic acid = 5,5-dimethyl-1-methoxymethoxy-2-
Oxo-3- (2,4-dichloro-6-methylphenyl) -2,5-dihydro-1H-pyrrol-4-yl =
Ester (Compound No. 10-139) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.24 (1H, s), 7.13 (1H, br)
ds), 5.04 (2H, s), 3.61 (3H, s), 2.26 (3H, s), 1.
68-1.48 (7H, m), 1.07-0.84 (4H, m). Physical properties: oil.

[0675]

Working Example 393 Cyclopropanecarboxylic acid = 5,5-dimethyl-1-methoxymethoxy-2-
Oxo-3- (3-chloro-2,4,6-trimethylphenyl) -2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 10-140) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.94 (1H, s), 5.05 (2H, s),
3.61 (3H, s), 2.33 (3H, s), 2.23 (3H, s), 2.13 (3
H, s), 1.68-1.58 (1H, m), 1.52 (3H, s), 1.50 (3H,
s), 0.98-0.76 (4H, m). Physical properties: Crystal (melting point: 78-79 ° C).

[0676]

Example 394 Cyclopropanecarboxylic acid = 5,5-dimethyl-1-methoxymethoxy-2-
Oxo-3- (2,3,4,6-tetramethylphenyl) -2,5-dihydro-1H-pyrrol-4-yl =
Ester (Compound No. 10-141) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.84 (1H, s), 5.05 (2H, s),
3.61 (3H, s), 2.23 (3H, s), 2.13 (3H, s), 2.11 (3
H, s), 2.10 (3H, s), 1.67-1.52 (1H, m), 1.51 (6H,
s), 1.11-0.78 (4H, m). Physical properties: amorphous.

[0677]

Working Example 395 Cyclopropanecarboxylic acid = 5,5-dimethyl-1-methoxymethoxy-2-
Oxo-3- (2,6-dimethyl-4-tert-butylphenyl) -2,5-dihydro-1H-pyrrole-4
-Yl = ester (Compound No. 10-142) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.01 (2H, s), 5.05 (2H, s),
3.61 (3H, s), 2.18 (6H, s), 1.70-1.15 (1H, m), 1.
50 (6H, s), 1.27 (9H, s), 0.89-0.68 (2H, m), 0.68-
0.59 (2H, m). Physical properties: Crystal (melting point: 124-126 ° C).

[0678]

Working Example 396 2-Methoxybenzoic acid =
5,5-dimethyl-1-methoxymethoxy-2-oxo-3- (2,6-dimethyl-4-methoxyphenyl)-
2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 10-143) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.69-7.65 (1H, m), 7.54-7.4
7 (1H, m), 7.00-6.92 (2H, m), 6.55 (2H, s), 5.08
(2H, s), 3.84 (3H, s), 3.73 (3H, s), 3.63 (3H, s),
2.24 (6H, s), 1.56 (6H, s). Physical properties: crystals (melting point: 104-105 ° C).

[0679]

Working Example 397 Cyclopropanecarboxylic acid = 5,5-dimethyl-1-methoxymethoxy-2-
Oxo-3- (2,6-dimethyl-4-methoxyphenyl) -2,5-dihydro-1H-pyrrol-4-yl =
Ester (Compound No. 10-144) ¹ H-NMR (CDCl ₃ ) δ (ppm): 6.58 (2H, s), 5.05 (2H, s),
3.77 (3H, s), 3.61 (3H, s), 2.17 (6H, s), 1.67-1.
55 (1H, m), 1.50 (6H, s), 0.92-0.80 (4H, m). Physical properties: crystals (melting point: 121-123 ° C).

[0680]

Working Example 398 2-methoxybenzoic acid =
1-ethoxymethoxy-5,5-dimethyl-2-oxo-3- (2,6-dimethyl-4-methoxyphenyl)-
2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 10-145) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.69-7.10 (2H, m), 7.00-6.9
3 (2H, m), 6.55 (2H, s), 5.13 (2H, s), 3.89 (2H,
q, J = 6.9), 3.73 (3H, s), 2.24 (6H, s), 1.56 (6H,
s), 1.30 (3H, t, J = 6.9). Physical properties: Crystal (melting point: 72-77 ° C).

[0681]

Working Example 399 Acetic acid = 5,5-dimethyl-1-methoxymethoxy-2-oxo-3- (2
6-dimethylphenyl) -2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 10-14)
6) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.12-7.01 (3H, m), 5.05 (2
H, s), 3.61 (3H, s), 2.20 (6H, s), 2.04 (3H, s),
1.50 (6H, s). Physical properties: Crystal (melting point: 87-89 ° C).

[0682]

Example 400 Isobutylic acid = 5,5-dimethyl-1-methoxymethoxy-2-oxo-3-
(2,6-dimethylphenyl) -2,5-dihydro-1
H-pyrrol-4-yl ester (Compound No. 10-
147) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.14-6.98 (3H, m), 5.06 (2
H, s), 3.62 (3H, s), 2.61-2.50 (1H, m), 2.20 (6H,
s), 1.50 (6H, s), 0.99 (6H, d, J = 6.9). Physical properties: Crystal (melting point: 99-100 ° C).

[0683]

Example 401 Cyclopropanecarboxylic acid = 5,5-dimethyl-1-methoxymethoxy-2-
Oxo-3- (2,6-dimethylphenyl) -2,5-
Dihydro-1H-pyrrol-4-yl ester (Compound No. 10-148) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.70-7.00 (3H, m), 5.05 (2
H, s), 3.61 (3H, s), 2.19 (6H, s), 1.67-1.54 (1H,
m), 1.51 (6H, s), 0.87-0.83 (2H, m), 0.79-0.76 (2
H, m). Physical properties: crystals (melting point: 136-138 ° C).

[0684]

Example 402 1-methylcyclopropanecarboxy
Ric acid = 5,5-dimethyl-1-methoxymeth
Xy-2-oxo-3- (2,6-dimethylphenyl)
-2,5-dihydro-1H-pyrrol-4-yl = es
Ter (Compound No. 10-149) ¹ H-NMR (CDCl_Three) δ (ppm): 7.15-6.97 (3H, m), 5.05 (2
H, s), 3.61 (3H, s), 2.19 (6H, s), 1.49 (6H, s),
1.23 (3H, s), 1.06-1.01 (2H, m), 0.70-0.64 (2H,
m). Physical properties: crystals (melting point: 104-107 ° C).

[0685]

Example 403 2-Methylcyclopropanecarboxy
Ric acid = 5,5-dimethyl-1-methoxymeth
Xy-2-oxo-3- (2,6-dimethylphenyl)
-2,5-dihydro-1H-pyrrol-4-yl = es
Ter (Compound No. 10-150) ¹ H-NMR (CDCl_Three) δ (ppm): 7.16-7.00 (3H, m), 5.05 (2
H, s), 3.61 (3H, s), 2.19 (6H, s), 1.51 (6H, s),
1.37-1.31 (1H, m), 1.10-0.93 (5H, m), 0.70-0.66 (1
H, m). Physical properties: Crystal (melting point: 66-68 ° C).

[0686]

Example 404 2,2-Dichloro-1-methylcyclopropanecarboxylic acid = 5,5-dimethyl-1-methoxymethoxy-2-oxo-3- (2,6-
(Dimethylphenyl) -2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 10-151) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.13-6.95 (3H, m), 5.06 ( Two
H, s), 3.62 (3H, s), 2.22 (3H, s), 2.20 (3H, s),
2.11 (1H, d, J = 7.7), 1.55 (3H, s), 1.52 (3H, s),
1.41 (3H, s), 1.38 (1H, d, J = 7.7). Physical properties: oil.

[0687]

Working Example 405 2,2-Dimethylbutyric acid = 5,5-dimethyl-1-methoxymethoxy-2-oxo-3- (2,6-dimethylphenyl) -2,5-dihydro-1H-pyrrole- 4-yl ester (Compound No. 10-152) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.10-6.95 (3H, m), 5.06 (2
H, s), 3.62 (2H, s), 2.20 (6H, s), 1.60-1.38 (2H,
m), 1.49 (6H, s), 1.03 (6H, s), 0.53 (3H, t, J = 7.
2). Physical properties: Crystal (melting point: 60-61 ° C).

[0688]

Working Example 406 3-Chloro-2,2-dimethylpropionic acid = 5,5-dimethyl-1-methoxymethoxy-2-oxo-3- (2,6-dimethylphenyl) -2,5-dihydro -1H-pyrrol-4-yl =
Ester (Compound No. 10-153) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.11-6.90 (3H, m), 5.06 (2
H, s), 3.62 (3H, s), 3.51 (2H, s), 2.20 (6H, s),
1.52 (6H, s), 1.08 (6H, s). Physical properties: crystals (melting point: 84-88 ° C).

[0689]

Working Example 407 3-Chloropropionic Acid =
5,5-dimethyl-1-methoxymethoxy-2-oxo-3- (2,6-dimethylphenyl) -2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 10-154) ¹ H -NMR (CDCl ₃ ) δ (ppm): 7.12-7.00 (3H, m), 5.06 (2
H, s), 3.61 (3H, s), 3.58 (2H, t, J = 6.4), 2.77 (2
H, t, J = 6.4), 2.19 (6H, s), 1.52 (6H, s). Physical properties: crystals (melting point: 84-87 ° C).

[0690]

Working Example 408 Cyclobutanecarboxylic acid = 5,5-dimethyl-1-methoxymethoxy-2-oxo-3- (2,6-dimethylphenyl) -2,5-dihydro-1H-pyrrol-4-yl = Ester (Compound No. 10-155) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.15-6.95 (3H, m), 5.06 (2
H, s), 3.61 (3H, s), 3.25-3.05 (1H, m), 2.35-1.68
(6H, m), 2.20 (6H, s), 1.50 (6H, s). Physical properties: crystals (melting point: 106-110 ° C).

[0691]

Example 409 Cyclopentanecarboxylic acid = 5,5-dimethyl-1-methoxymethoxy-2-
Oxo-3- (2,6-dimethylphenyl) -2,5-
Dihydro-1H-pyrrol-4-yl ester (Compound No. 10-156) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.15-6.95 (3H, m), 5.06 (2
H, s), 3.62 (3H, s), 2.82-2.67 (1H, m), 2.20 (6H,
s), 1.95-1.38 (8H, m), 1.50 (6H, s). Physical properties: oil.

[0692]

Example 410 Cyclohexanecarboxylic acid = 5,5-dimethyl-1-methoxymethoxy-2-
Oxo-3- (2,6-dimethylphenyl) -2,5-
Dihydro-1H-pyrrol-4-yl ester (Compound No. 10-157) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.13-6.95 (3H, m), 5.06 (2
H, s), 3.61 (3H, s), 2.40-2.25 (1H, m), 2.19 (6H,
s), 2.00-1.10 (10H, m), 1.49 (6H, s). Physical properties: oil.

[0693]

Example 411 2-chloroacrylic acid =
5,5-dimethyl-1-methoxymethoxy-2-oxo-3- (2,6-dimethylphenyl) -2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 10-158) ¹ H -NMR (CDCl ₃ ) δ (ppm): 7.15-6.98 (3H, m), 6.51 (1
H, d, J = 2.0), 6.07 (1H, d, J = 2.0), 5.06 (2H, s), 3.
62 (3H, s), 2.21 (6H, s), 1.54 (6H, s). Physical properties: Crystal (melting point: 81-83 ° C).

[0694]

Example 412 2-chlorobenzoic acid =
5,5-dimethyl-1-methoxymethoxy-2-oxo-3- (2,6-dimethylphenyl) -2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 10-159) ¹ H -NMR (CDCl ₃ ) δ (ppm): 7.58-7.23 (4H, m), 7.15-6.9
7 (3H, m), 5.09 (2H, s), 3.64 (3H, s), 2.25 (6H,
s), 1.60 (6H, s). Physical properties: Crystal (melting point: 94-99 ° C).

[0696]

Working Example 413 2-methylbenzoic acid =
5,5-Dimethyl-1-methoxymethoxy-2-oxo-3- (2,6-dimethylphenyl) -2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 10-160) ¹ H -NMR (CDCl ₃ ) δ (ppm): 7.84-7.80 (1H, m), 7.45-7.3
7 (1H, m), 7.28-7.18 (2H, m), 7.10-6.93 (3H, m),
5.09 (2H, s), 3.63 (3H, s), 2.31 (3H, s), 2.25 (6
H, s), 1.59 (6H, s). Physical properties: Crystal (melting point: 76-78 ° C).

[0696]

Example 414 Methyl carbonate = 5,5-dimethyl-1-methoxymethoxy-2-oxo-3-
(2,6-dimethylphenyl) -2,5-dihydro-1
H-pyrrol-4-yl ester (Compound No. 10-
161) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.14-7.02 (3H, m), 5.05 (2
H, s), 3.61 (3H, s), 3.58 (3H, s), 2.20 (2H, s),
1.54 (6H, s). Physical properties: crystals (melting point: 158-160 ° C).

[0697]

Example 415 Ethyl carbonate = ester = 5,5-dimethyl-1-methoxymethoxy-2-oxo-3-
(2,6-dimethylphenyl) -2,5-dihydro-1
H-pyrrol-4-yl ester (Compound No. 10-
162) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.13-7.01 (3H, m), 5.05 (2
H, s), 3.98 (2H, q, J = 7.0), 3.61 (3H, s), 2.20 (6
H, s), 1.54 (6H, s), 1.06 (3H, t, J = 7.0). Physical properties: crystals (melting point: 69-73 ° C).

[0698]

Example 416 Thiocarbonic acid = S-methyl ester = O- [5,5-dimethyl-1-methoxymethoxy-2-oxo-3- (2,6-dimethylphenyl) -2,5-dihydro-1H -Pyrrole-4-yl]
Ester (Compound No. 10-163) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.16-7.00 (3H, m), 5.05 (2
H, s), 3.61 (3H, s), 2.19 (6H, s), 2.17 (3H, s),
1.52 (6H, s). Physical properties: Crystal (melting point: 98-102 ° C).

[0699]

Example 417 Dimethylcarbamic acid = 5
5-dimethyl-1-methoxymethoxy-2-oxo-3
-(2,6-dimethylphenyl) -2,5-dihydro-
[1H-pyrrol-4-yl] ester (Compound No. 10
-164) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.15-7.00 (3H, m), 5.06 (2
H, s), 3.62 (3H, s), 2.91 (3H, s), 2.72 (3H, s),
2.21 (6H, s), 1.53 (6H, s). Physical properties: crystals (melting point: 110-111 ° C).

[0700]

Working Example 418 Dimethylthiocarbamic Acid =
5,5-Dimethyl-1-methoxymethoxy-2-oxo-3- (2,6-dimethylphenyl) -2,5-dihydro-1H-pyrrol-4-yl] ester (Compound No. 10-165) ¹ H -NMR (CDCl ₃ ) δ (ppm): 7.15-6.98 (3H, m), 5.06 (2
H, s), 3.62 (3H, s), 3.18 (6H, s), 2.26 (6H, s),
1.57 (6H, s). Physical properties: Crystal (melting point: 151-155 ° C).

[0701]

Example 419 4-ethoxymethoxy-5,5-dimethyl-1-methoxymethoxy-2-oxo-3- (2
6-dimethylphenyl) -2,5-dihydro-1H-pyrrole (Compound No. 10-166) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.13-7.01 (3H, m), 5.02 (2
H, s), 4.73 (2H, s), 3.59 (3H, s), 3.58 (2H, q, J =
7.2), 2.19 (6H, s), 1.51 (6H, s), 1.15 (3H, t, J =
7.2). Physical properties: oil.

[0702]

Example 420 Cyclopropanecarboxylic acid = 1-ethoxymethoxy-5,5-dimethyl-2-
Oxo-3- (2,6-dimethylphenyl) -2,5-
Dihydro-1H-pyrrol-4-yl ester (Compound No. 10-167) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.14-6.98 (3H, m), 5.11 (2
H, s), 3.87 (2H, q, J = 2.0), 2.19 (6H, s), 1.70-1.5
0 (1H, m), 1.51 (6H, s), 1.29 (3H, t, J = 7.0), 0.95-
0.70 (4H, m). Physical properties: Crystal (melting point: 103-104 ° C).

[0703]

Example 421 1-methylcyclopropanecarboxy
Rick acid = 1-ethoxymethoxy-5,5-dim
Tyl-2-oxo-3- (2,6-dimethylphenyl)
-2,5-dihydro-1H-pyrrol-4-yl = es
Ter (Compound No. 10-168) ¹ H-NMR (CDCl_Three) δ (ppm): 7.15-6.95 (3H, m), 5.10 (2
H, s), 3.87 (2H, q, J = 7.0), 2.19 (6H, s), 1.49 (6
H, s), 1.29 (3H, t, J = 7.0), 1.22 (3H, s), 1.06-1.0
1 (2H, m), 0.69-0.64 (2H, m). Physical properties: Crystal (melting point: 88-91 ° C).

[0704]

Example 422 1-Phenylcyclopropanecarboxylic acid = 1-ethoxymethoxy-5,5-dimethyl-2-oxo-3- (2,6-dimethylphenyl) -2,5-dihydro-1H-pyrrole- 4-yl =
Ester (Compound No. 10-169) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.30-7.26 (3H, m), 7.20-7.1
3 (3H, m), 7.06-7.02 (2H, m), 5.07 (2H, s), 3.84
(2H, q, J = 7.1), 2.08 (6H, s), 1.40-1.30 (2H, m), 1.
36 (6H, s), 1.27 (3H, t, J = 7.1), 1.19-1.13 (2H,
m). Physical properties: oil.

[0705]

Working Example 423 1- (4-ethoxyphenyl) -2,
2-dichlorocyclopropanecarboxylic acid = 1-ethoxymethoxy-5,5-dimethyl-2-oxo-3- (2,6-dimethylphenyl) -2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 10-170) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.24-7.16 (2H, m), 7.06-6.7
6 (5H, m), 5.08 (2H, s), 4.06 (3H, t, J = 7.0), 3.84
(3H, t, J = 7.3), 2.44 (1H, d, J = 7.7), 2.20 (3H,
s), 1.89 (1H, d, J = 7.7), 1.78 (3H, s), 1.45 (3H,
t, J = 7.0), 1.42 (3H, s), 1.38 (3H, s), 1.27 (3H,
t, J = 7.3). Physical properties: oil.

[0706]

Example 424 Cyclobutanecarboxylic acid = 1-ethoxymethoxy-5,5-dimethyl-2-oxo-3- (2,6-dimethylphenyl) -2,5-dihydro-1H-pyrrol-4-yl = Ester (Compound No. 10-171) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.15-6.95 (3H, m) 5.11 (2H,
s) 3.87 (2H, q, J = 7.0) 3.23-3.05 (1H, m) 2.30-1.6
0 (6H, m) 2.20 (6H, s) 1.49 (6H, s) 1.29 (3H, t, J
= 7.0). Physical properties: crystals (melting point: 99-102 ° C).

[0707]

Working Example 425 2-Chloroacrylic Acid = 1
-Ethoxymethoxy-5,5-dimethyl-2-oxo-
3- (2,6-dimethylphenyl) -2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 1
0-172) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.15-6.97 (3H, m), 6.51 (1
H, d, J = 1.8), 6.07 (1H, d, J = 1.8), 5.12 (2H, s), 3.
88 (2H, q, J = 7.0), 2.21 (6H, s), 1.54 (6H, s), 1.2
9 (3H, t, J = 7.0). Physical properties: crystals (melting point: 89-91 ° C).

[0708]

Example 426 3-Methyloxetane-3-carboxylic acid = 1-ethoxymethoxy-5,5-dimethyl-2-oxo-3- (2,6-dimethylphenyl) -2,5-dihydro-1H- Pyrrole-4-yl =
Ester (Compound No. 10-173) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.16-6.99 (3H, m), 5.12 (2
H, s), 4.64 (2H, d, J = 6.2), 4.30 (2H, d, J = 6.2),
3.88 (2H, q, J = 7.3), 2.20 (6H, s), 1.52 (6H, s),
1.43 (3H, s), 1.30 (3H, t, J = 7.3). Physical properties: crystals (melting point: 109-113 ° C).

[0709]

Working Example 427 2-Chlorobenzoic acid = 1
-Ethoxymethoxy-5,5-dimethyl-2-oxo-
3- (2,6-dimethylphenyl) -2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 1
0-174) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.57-7.23 (4H, m), 7.16-6.9
6 (3H, m), 5.14 (2H, s), 3.89 (2H, q, J = 7.0), 2.25
(6H, s), 1.60 (6H, s), 1.30 (3H, t, J = 7.0). Physical properties: oil.

[0710]

Working Example 428 2-Methylbenzoic acid = 1
-Ethoxymethoxy-5,5-dimethyl-2-oxo-
3- (2,6-dimethylphenyl) -2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 1
0-175) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.84-7.79 (1H, m), 7.45-7.3
7 (1H, m), 7.30-7.18 (2H, m), 7.10-6.93 (3H, m),
5.14 (2H, s), 3.89 (2H, q, J = 7.0), 2.31 (3H, s), 2.
24 (6H, s), 1.59 (6H, s), 1.30 (3H, t, J = 7.0). Physical properties: oil.

[0711]

Working Example 429 2-methoxybenzoic acid =
1-ethoxymethoxy-5,5-dimethyl-2-oxo-3- (2,6-dimethylphenyl) -2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 10-176) ¹ H -NMR (CDCl ₃ ) δ (ppm): 7.67-7.60 (1H, m), 7.53-7.4
3 (1H, m), 7.10-6.90 (5H, m), 5.14 (2H, s), 3.89
(2H, q, J = 7.0), 3.82 (3H, s), 2.26 (6H, s), 1.57
(6H, s), 1.30 (3H, t, J = 7.0). Physical properties: crystals (melting point: 111-114 ° C).

[0712]

Working Example 430 Thiophosphonic Acid = O, O ′
-Diethyl ester = O "-[1-ethoxymethoxy-
5,5-dimethyl-2-oxo-3- (2,6-dimethylphenyl) -2,5-dihydro-1H-pyrrole-4
-Yl] ester (Compound No. 10-177) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.16-6.99 (3H, m), 5.30 (2
H, s), 3.92-3.73 (4H, m), 3.65-3.48 (2H, m), 2.25
(6H, s), 1.55 (6H, s), 1.28 (3H, t, J = 7.0), 1.14
(6H, t, J = 7.0). Physical properties: oil.

[0713]

Example 431 Cyclopropanecarboxylic acid = 5,5-dimethyl-1-methoxyethoxy-2-
Oxo-3- (2,6-dimethylphenyl) -2,5-
Dihydro-1H-pyrrol-4-yl ester (Compound No. 10-178) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.13-6.95 (3H, m), 4.32-4.2
7 (2H, m), 3.73-3.67 (2H, m), 3.43 (3H, s), 2.19
(6H, s), 1.67-1.53 (1H, m), 1.52 (6H, s), 0.88-0.7
5 (4H, m). Physical properties: oil.

[0714]

Example 432 1-methylcyclopropanecarboxy
Rick acid = 5,5-dimethyl-1-methoxyeth
Xy-2-oxo-3- (2,6-dimethylphenyl)
-2,5-dihydro-1H-pyrrol-4-yl = es
Ter (Compound No. 10-179) ¹ H-NMR (CDCl_Three) δ (ppm): 7.15-6.95 (3H, m), 4.33-4.2
6 (2H, m), 3.73-3.67 (2H, m), 3.43 (3H, s), 2.18
(6H, s), 1.50 (6H, s), 1.22 (3H, s), 1.06-1.01 (2
H, m), 0.69-0.64 (2H, m). Physical properties: oil.

[0715]

Example 433 Cyclobutanecarboxylic acid = 5,5-dimethyl-1-methoxyethoxy-2-oxo-3- (2,6-dimethylphenyl) -2,5-dihydro-1H-pyrrol-4-yl = Ester (Compound No. 10-180) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.15-6.97 (3H, m), 4.33-4.2
7 (2H, m), 3.75-3.68 (2H, m), 3.43 (3H, s), 3.23-
3.05 (1H, m), 2.40-1.65 (6H, m), 2.19 (6H, s), 1.5
0 (6H, s). Physical properties: oil.

[0716]

Example 434 2,2-Dimethylbutyric acid = 5,5-dimethyl-1-methoxyethoxy-2-oxo-3- (2,6-dimethylphenyl) -2,5-dihydro-1H-pyrrole- 4-yl ester (Compound No. 10-181) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.15-6.93 (3H, m), 4.35-4.2
7 (2H, m), 3.75-3.67 (2H, m), 3.43 (3H, s), 2.20
(6H, s), 1.50 (6H, s), 1.45 (2H, q, J = 7.3), 1.02
(6H, s), 0.53 (3H, t, J = 7.3). Physical properties: oil.

[0717]

Example 435 3-chloro-2,2-dimethylpropionic acid = 5,5-dimethyl-1-methoxyethoxy-2-oxo-3- (2,6-dimethylphenyl) -2,5-dihydro -1H-pyrrol-4-yl =
Ester (Compound No. 10-182) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.15-6.95 (3H, m), 4.35-4.2
8 (2H, m), 3.75-3.68 (2H, m), 3.50 (2H, s), 3.43
(3H, s), 2.20 (6H, s), 1.53 (6H, s), 1.08 (6H,
s). Physical properties: oil.

[0718]

Working Example 436 2-acetoxy-2-methylpropio
Nick Acid = 5,5-dimethyl-1-methoxyeth
Xy-2-oxo-3- (2,6-dimethylphenyl)
-2,5-dihydro-1H-pyrrol-4-yl = es
Ter (Compound No. 10-183) ¹ H-NMR (CDCl_Three) δ (ppm): 7.15-6.95 (3H, m), 4.35-4.2
8 (2H, m), 3.75-3.68 (2H, m), 3.43 (3H, s), 2.19
(6H, s), 1.52 (6H, s), 1.24 (6H, s). Physical properties: Crystal (melting point: 59-61 ° C).

[0719]

Working Example 437 2-Methylbenzoic acid =
5,5-Dimethyl-1-methoxyethoxy-2-oxo-3- (2,6-dimethylphenyl) -2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 10-184) ¹ H -NMR (CDCl ₃ ) δ (ppm): 7.83-7.88 (1H, m), 7.46-7.3
8 (1H, m), 7.30-7.18 (2H, m), 7.10-6.95 (3H, m),
4.37-4.30 (2H, m), 3.75-3.70 (2H, m), 3.44 (3H,
s), 2.32 (3H, s), 2.24 (6H, s), 1.59 (6H, s). Physical properties: oil.

[0720]

Working Example 438 2-Chlorobenzoic acid =
5,5-Dimethyl-1-methoxyethoxy-2-oxo-3- (2,6-dimethylphenyl) -2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 10-185) ¹ H -NMR (CDCl ₃ ) δ (ppm): 7.58-7.23 (4H, m), 7.15-6.9
8 (3H, m), 4.38-4.32 (2H, m), 3.77-3.70 (2H, m),
3.44 (3H, s), 2.25 (6H, s), 1.60 (6H, s). Physical properties: oil.

[0721]

Working Example 439 2-methoxybenzoic acid =
5,5-Dimethyl-1-methoxyethoxy-2-oxo-3- (2,6-dimethylphenyl) -2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 10-186) ¹ H -NMR (CDCl ₃ ) δ (ppm): 7.66-7.60 (1H, m), 7.53-7.4
3 (1H, m), 7.10-6.88 (5H, m), 4.35-4.30 (2H, m),
3.82 (3H, s), 3.75-3.70 (2H, m), 3.44 (3H, s), 2.2
6 (6H, s), 1.58 (6H, s). Physical properties: Crystal (melting point: 65-67 ° C).

[0722]

EXAMPLE 440 Ethyl carbonate = ester = 5,5-dimethyl-1-methoxyethoxy-2-oxo-3-
(2,6-dimethylphenyl) -2,5-dihydro-1
H-pyrrol-4-yl ester (Compound No. 10-
187) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.16-6.98 (3H, m), 4.33-4.2
7 (2H, m), 3.75-3.68 (2H, m), 3.59 (3H, s), 3.43
(3H, s), 2.20 (6H, s), 1.55 (6H, s). Physical properties: oil.

[0723]

Example 441 4-cyanomethoxy-5,5-dimethyl-1-methoxyethoxy-2-oxo-3- (2,6
-Dimethylphenyl) -2,5-dihydro-1H-pyrrole (Compound No. 10-188) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.25-7.05 (3H, m), 4.38 (2
H, s), 4.30-4.23 (2H, m), 3.73-3.66 (2H, m), 3.42
(3H, s), 2.23 (6H, s), 1.53 (6H, s). Physical properties: Crystal (melting point: 101-103 ° C).

[0724]

Example 442 5,5-Dimethyl-1-methoxyethoxy-4-methoxymethoxy-2-oxo-3- (2
6-dimethylphenyl) -2,5-dihydro-1H-pyrrole (Compound No. 10-189) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.15-6.98 (3H, m), 4.67 (2
H, s), 4.27-4.22 (2H, m), 3.74-3.67 (2H, m), 3.42
(3H, s), 3.36 (3H, s), 2.18 (6H, s), 1.53 (6H,
s). Physical properties: oil.

[0725]

Working Example 443 5,5-Dimethyl-1-methoxyethoxy-4-methylthiomethoxy-2-oxo-3-
(2,6-dimethylphenyl) -2,5-dihydro-1
H-pyrrole (Compound No. 10-190) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.15-7.00 (3H, m), 4.71 (2
H, s), 4.28-4.22 (2H, m), 3.72-3.68 (2H, m), 3.42
(3H, s), 2.21 (6H, s), 2.15 (3H, s), 1.51 (6H,
s). Physical properties: oil.

[0726]

Example 444 Cyclopropanecarboxylic acid = 5,5-dimethyl-1-hydroxy-2-oxo-3- (2,6-dimethylphenyl) -2,5-dihydro-1H-pyrrol-4-yl = Ester (Compound No. 10-191) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.11-6.99 (3H, m), 2.16 (6
H, s), 1.67-1.55 (1H, m), 1.46 (6H, s), 0.85-0.77
(4H, m). Physical properties: Crystal (melting point: 125-128 ° C).

[0727]

Example 445 Cyclopropanecarboxylic acid = 5,5-dimethyl-1-propyl-2-oxo-
3- (2,6-dimethylphenyl) -2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 1
0-192) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.13-6.99 (3H, m), 4.11 (2
(H, t, J = 6.6), 2.19 (6H, s), 1.90-1.70 (2H, m), 1.68
-1.56 (1H, m), 1.03 (3H, t, J = 7.2), 0.88-0.78 (4H,
m). Physical properties: oil.

[0728]

Example 446: Cyclopropanecarboxylic acid = 5,5-dimethyl-1-cyclopropyl-2-oxo-3- (2,6-dimethylphenyl) -2,5-dihydro-1H-pyrrol-4-yl = Ester (Compound No. 10-193) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.14-6.90 (3H, m), 3.98 (2
(H, d, J = 7.0), 2.19 (6H, s), 1.51 (6H, s), 1.40-0.75
(6H, m), 0.70-0.58 (2H, m), 0.40-0.34 (2H, m). Physical properties: oil.

[0729]

Working Example 447 Cyclopropanecarboxylic acid = 5,5-dimethyl-1- (2-propynyl) -2
-Oxo-3- (2,6-dimethylphenyl) -2,5
-Dihydro-1H-pyrrol-4-yl ester (Compound No. 10-194) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.09-7.00 (3H, m), 4.94 (2
H, d, J = 2.6), 2.57 (1H, t, J = 2.6), 2.19 (6H, s), 1.
70-1.54 (1H, m), 1.53 (6H, s), 0.87-0.83 (2H, m),
0.79-0.75 (2H, m). Physical properties: crystals (melting point: 103-107 ° C).

[0730]

Working Example 448 3,3-Dimethylbutyric acid = 5,5-dimethyl-1-cyanomethyl-2-oxo-
3- (2,6-dimethylphenyl) -2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 1
0-195) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.12-7.00 (3H, m), 4.91 (2
H, s), 2.19 (6H, s), 2.18 (2H, s), 1.55 (6H, s),
0.81 (9H, s). Physical properties: crystals (melting point: 113-114 ° C).

[0731]

Example 449 Cyclopropanecarboxylic acid = 5,5-dimethyl-1- (3-methoxypropyl) -2-oxo-3- (2,6-dimethylphenyl)
-2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 10-196) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.12-6.98 (3H, m), 4.24 (2
H, t, J = 6.0), 3.59 (2H, t, J = 6.0), 3.37 (3H, s), 2.
19 (6H, s), 2.12-1.98 (2H, m), 1.65-1.50 (1H, m),
1.56 (6H, s), 0.87-0.76 (4H, m). Physical properties: oil.

[0732]

Example 450 Cyclopropanecarboxylic acid = 5,5-dimethyl-1- (2-methoxy-1-methylethyl) -2-oxo-3- (2,6-dimethylphenyl) -2,5-dihydro -1H- pyrrol-4-yl = ester (compound No. ^{10-197) 1 H-NMR (CDCl} 3) δ (ppm): 7.13-6.98 (3H, m), 4.40-4.2
0 (1H, m), 3.64-3.54 (2H, m), 3.41 (3H, s), 2.19
(6H, s), 1.62-1.57 (1H, m), 1.51 (6H, s), 1.30 (3
H, d, J = 6.4), 0.86-0.76 (4H, m). Physical properties: oil.

[0733]

Working Example 451 2-Methoxybenzoic acid =
5,5-dimethyl-1- (tetrahydrofuran-3-ylmethyl) -2-oxo-3- (2,6-dimethylphenyl) -2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 10 -198) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.66-7.46 (2H, m), 7.10-6.9
2 (5H, m), 4.25-4.05 (2H, m), 4.10-3.82 (2H, m),
3.82 (3H, s), 3.81-3.77 (2H, m), 2.90-2.70 (1H,
m), 2.27 (3H, s), 2.26 (3H, s), 2.25-2.10 (1H, m),
1.85-1.70 (1H, m), 1.57 (6H, s). Physical properties: Crystal (melting point: 99-100 ° C).

[0734]

Working Example 452 2-Methylbenzoic acid =
5,5-dimethyl-1- (tetrahydrofuran-3-ylmethyl) -2-oxo-3- (2,6-dimethylphenyl) -2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 10 -199) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.83-7.80 (1H, m), 7.45-7.4
0 (1H, m), 7.26-7.19 (2H, m), 7.01-6.96 (3H, m),
4.21-4.04 (2H, m), 3.97-3.85 (2H, m), 3.80-3.72 (2
H, m), 2.80-2.75 (1H, m), 2.32 (3H, s), 2.25 (3H,
s), 2.24 (3H, s), 2.16-2.04 (1H, m), 1.77-1.70 (1H,
m), 1.58 (6H, s). Physical properties: Crystal (melting point: 103-106 ° C).

[0735]

Working Example 453 Cyclopropanecarboxylic acid = 5,5-dimethyl-1- (tetrahydrofuran-
3-yl) -2-oxo-3- (2,6-dimethylphenyl) -2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 10-200) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.14-7.00 (3H, m), 4.96-4.9
3 (1H, m), 4.17-4.02 (2H, m), 3.93-3.82 (1H, m),
2.45-2.33 (1H, m), 2.19 (3H, s), 2.18 (3H, s), 2.1
7-2.00 (1H, m), 1.70-1.50 (1H, m), 1.50 (6H, s),
0.88-0.75 (4H, m). Physical properties: oil.

[0736]

Working Example 454 2-methoxybenzoic acid =
5,5-dimethyl-1- (tetrahydrofuran-3-i
Ru) -2-oxo-3- (2,6-dimethylphenyl)
-2,5-dihydro-1H-pyrrol-4-yl = es
Ter (Compound No. 10-201) ¹ H-NMR (CDCl_Three) δ (ppm): 7.66-7.63 (1H, m), 7.53-7.4
6 (1H, m), 7.10-6.92 (5H, m), 4.99-4.96 (1H, m),
4.17 (1H, d, J = 10.7), 4.07 (1H, q, J = 6.9), 3.83-3.
77 (2H, m), 3.83 (3H, s), 2.48-2.35 (1H, m), 2.27
(3H, s), 2.25 (3H, s), 2.20-2.00 (1H, m), 1.57 (6
H, s). Physical properties: crystals (melting point: 131-134 ° C).

[0737]

Example 455 3-Methyloxetane-3-carboxylic acid = 5,5-dimethyl-1-methoxymethoxy-2-oxo-3- (2,6-dimethylphenyl) -2,5-dihydro-1H- Pyrrole-4-yl =
Ester (Compound No. 10-202) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.17-7.00 (3H, m), 5.07 (2H,
s), 4.64 (2H, d, J = 6.2), 4.30 (2H, d, J = 6.2), 3.6
2 (3H, s), 2.20 (6H, s), 1.52 (6H, s), 1.43 (3H,
s). Physical properties: oil.

[0738]

Example 456 2-Methoxy-2-methylpropionic acid = 5,5-dimethyl-1-methoxymethoxy-2-oxo-3- (2,6-dimethylphenyl)-
2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 10-203) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.14-6.98 (3H, m), 5.07 (2H,
s), 3.62 (3H, s), 2.94 (3H, s), 2.21 (6H, s), 1.5
2 (6H, s), 1.27 (6H, s). Physical properties: oil.

[0739]

Working Example 457 2-Methoxy-2-methylpropionic acid = 1-ethoxymethoxy-5,5-dimethyl-2-oxo-3- (2,6-dimethylphenyl)-
2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 10-209) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.14-6.98 (3H, m), 5.12 (2H,
s), 3.88 (2H, q, J = 7.0), 2.94 (3H, s), 2.21 (6H,
s), 1.51 (6H, s), 1.29 (3H, t, J = 7.0), 1.26 (6H,
s). Physical properties: crystals (melting point: 72-75 ° C).

[0740]

Working Example 458 Cyclopropanecarboxylic acid = 5,5-dimethyl-1-methoxymethyl-2-oxo-3- (2,4-dichlorophenyl) -2,5-dihydro-1H-pyrrol-4-yl = Ester (Compound No. 10-221) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.41-7.24 (3H, m), 5.04 (2
H, s), 3.62 (3H, s), 1.81-1.67 (1H, m), 1.50 (6H,
s), 1.08-0.95 (4H, m). Physical properties: oil.

[0741]

Working Example 459 1-Methylcyclopropanecarboxylic acid = 5,5-dimethyl-1-methoxymethyl-2-oxo-3- (2,4-dichlorophenyl)-
2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 10-222) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.50-7.28 (3H, m), 5.04 (2
H, s), 3.62 (3H, s), 1.48 (6H, s), 1.24 (2H, dd, J
= 3.6, 2.9), 0.83 (2H, dd, J = 3.6, 2.9). Physical properties: Crystal (melting point: 100-101 ° C).

[0742]

Example 460 2-Methylcyclopropanecarboxylic acid = 5,5-dimethyl-1-methoxymethyl-2-oxo-3- (2,4-dichlorophenyl)-
2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 10-223) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.43-7.24 (3H, m), 5.04 (2
H, s), 3.62 (3H, s), 1.54-1.10 (11H, m), 0.96-0.79
(2H, m). Physical properties: oil.

[0734]

Working Example 461 1-Cyanocyclopropanecarboxylic acid = 5,5-dimethyl-1-methoxymethyl-2-oxo-3- (2,4-dichlorophenyl)-
2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 10-224) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.40-7.28 (3H, m), 5.05 (2
H, s), 3.63 (3H, s), 1.75-1.67 (2H, m), 1.66-1.60
(2H, m), 1.57 (6H, s). Physical properties: oil.

[0744]

Example 462 2,2-Dichloro-1-methylcyclopropanecarboxylic acid = 5,5-dimethyl-1-methoxymethyl-2-oxo-3- (2,4-dichlorophenyl) -2,5-dihydro -1H- pyrrol-4-yl = ester (compound No. ^{10-225) 1 H-NMR (CDCl} 3) δ (ppm): 7.42-7.26 (3H, m), 5.05 (2
H, s), 3.62 (3H, s), 2.28, 2.20 (1H, d, J = 7.7), 1.
65-1.44 (10H, m). Physical properties: oil.

[0745]

Working Example 463 2,2,3,3-Tetramethylcyclopropanecarboxylic acid = 5,5-dimethyl-1-methoxymethyl-2-oxo-3- (2,4-dichlorophenyl) -2,5- Dihydro-1H-pyrrol-4-yl ester (Compound No. 10-226) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.38-7.24 (3H, m), 5.04 (2
H, s), 3.62 (3H, s), 1.57 (1H, s), 1.50 (6H, s),
1.24 (6H, s), 0.98 (6H, s). Physical properties: Crystal (melting point: 95-96 ° C).

[0746]

Example 464 Cyclobutanecarboxylic acid = 5,5-dimethyl-1-methoxymethyl-2-oxo-3- (2,4-dichlorophenyl) -2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 10-227) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.41-7.27 (3H, m), 5.04 (2
H, s), 3.62 (3H, s), 2.38-1.78 (7H, m), 1.48 (6H,
s). Physical properties: oil.

[0747]

Example 465 3-Methyloxetane-3-carboxylic acid = 5,5-dimethyl-1-methoxymethoxy-2-oxo-3- (2,4-dichlorophenyl) -2,5-dihydro-1H-pyrrole -4-yl =
Ester (Compound No. 10-228) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.42-7.28 (3H, m), 5.05 (2
H, s), 4.86 (2H, d, J = 6.2), 4.42 (2H, d, J = 6.2),
3.62 (3H, s), 1.63 (3H, s), 1.51 (6H, s). Physical properties: oil.

[0748]

Working Example 466 2-Chloroacrylic acid =
5,5-dimethyl-1-methoxymethoxy-2-oxo-3- (2,4-dichlorophenyl) -2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 10-229) ¹ H- NMR (CDCl ₃ ) δ (ppm): 7.41-7.27 (3H, m), 6.64 (1
H, d, J = 1.8), 6.18 (1H, d, J = 1.8), 5.05 (2H, s), 3.
63 (3H, s), 1.54 (6H, s). Physical properties: Crystal (melting point: 77-78 ° C).

[0749]

Working Example 467 2-chlorobenzoic acid =
5,5-Dimethyl-1-methoxymethoxy-2-oxo-3- (2,4-dichlorophenyl) -2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 10-230) ¹ H- NMR (CDCl ₃ ) δ (ppm): 7.90-7.83 (1H, m), 7.52-7.2
6 (6H, m), 5.07 (2H, s), 3.64 (3H, s), 1.59 (6H,
s). Physical properties: oil.

[0750]

Working Example 468 Cyclopropanecarboxylic acid = 1-ethoxymethoxy-5,5-dimethyl-2
-Oxo-3- (2,4-dichlorophenyl) -2,5
-Dihydro-1H-pyrrol-4-yl ester (Compound No. 10-231) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.39-7.28 (3H, m), 5.09 (2
H, s), 3.87 (2H, q, J = 6.9), 1.76-1.68 (1H, m), 1.5
0 (6H, s), 1.28 (3H, t, J = 6.9), 1.09-0.88 (4H,
m). Physical properties: Crystal (melting point: 63-64 ° C).

[0751]

Example 469 1-methylcyclopropanecarboxy
Rick acid = 1-ethoxymethoxy-5,5-dim
Tyl-2-oxo-3- (2,4-dichlorophenyl)
-2,5-dihydro-1H-pyrrol-4-yl = es
Ter (Compound No. 10-232) ¹ H-NMR (CDCl_Three) δ (ppm): 7.40-7.27 (3H, m), 5.10 (2
H, s), 3.87 (2H, q, J = 6.9), 1.48 (6H, s), 1.87-1.1
9 (8H, m), 0.81 (2H, dd, J = 4.8, 2.9). Physical properties: Crystal (melting point: 70-71 ° C).

[0752]

Example 470 1-cyanocyclopropanecarboxy
Rick acid = 1-ethoxymethoxy-5,5-dim
Tyl-2-oxo-3- (2,4-dichlorophenyl)
-2,5-dihydro-1H-pyrrol-4-yl = es
Ter (Compound No. 10-233) ¹ H-NMR (CDCl_Three) δ (ppm): 7.38-7.27 (3H, m), 5.10 (2
H, s), 3.88 (2H, q, J = 6.9), 1.77 (2H, t, J = 3.7),
1.64 (2H, t, J = 3.7), 1.56 (6H, s), 1.30 (3H, t, J =
6.9). Physical properties: oil.

[0753]

Example 471 Cyclobutanecarboxylic acid 1-ethoxymethoxy-5,5-dimethyl-2-oxo-3- (2,4-dichlorophenyl) -2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 10-234) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.39-7.28 (3H, m), 5.09 (2
H, s), 3.87 (2H, q, J = 6.9), 3.28 (1H, septet, J = 8.
4), 2.38-1.79 (6H, m), 1.48 (6H, s), 1.29 (3H, t,
J = 6.9). Physical properties: crystals (melting point: 81-82 ° C).

[0754]

Working Example 472 3-Methyloxetane-3-carboxylic acid = 1-ethoxymethoxy-5,5-dimethyl-2-oxo-3- (2,4-dichlorophenyl) -2,5-dihydro-1H-pyrrole -4-yl =
Ester (Compound No. 10-235) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.45-7.27 (3H, m), 5.10 (2
H, s), 4.86 (2H, d, J = 6.2), 4.42 (2H, d, J = 6.2),
3.88 (2H, q, J = 7.3), 1.62 (3H, s), 1.51 (6H, s),
1.29 (3H, t, J = 7.3). Physical properties: oil.

[0755]

Working Example 473 2-Chloroacrylic acid = 1
-Ethoxymethoxy-5,5-dimethyl-2-oxo-
3- (2,4-dichlorophenyl) -2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 1)
0-236) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.40-7.28 (3H, m), 6.64 (1
H, d, J = 1.8), 6.18 (1H, d, J = 1.8), 5.11 (2H, s), 3.
88 (2H, q, J = 6.9), 1.54 (6H, s), 1.29 (3H, t, J = 6.
9). Physical properties: crystals (melting point: 67-68 ° C).

[0756]

Working Example 474 Benzoic acid = 1-ethoxymethoxy-5,5-dimethyl-2-oxo-3- (2
4-Dichlorophenyl) -2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 10-23)
7) ¹ H-NMR (CDCl ₃ ) δ (ppm): 8.05-8.06 (2H, m), 7.69-7.2
5 (6H, m), 5.13 (2H, s), 3.90 (2H, q, J = 7.0), 1.59
(6H, s), 1.30 (3H, t, J = 7.0). Physical properties: oil.

[0757]

Working Example 475 2-Methylbenzoic acid = 1
-Ethoxymethoxy-5,5-dimethyl-2-oxo-
3- (2,4-dichlorophenyl) -2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 1)
0-238) ¹ H-NMR (CDCl ₃ ) δ (ppm): 8.00 (1H, d, J = 7.7), 7.52-
7.18 (6H, s), 5.13 (2H, s), 3.99 (2H, q, J = 6.9), 2.
05 (3H, s), 1.58 (6H, s), 1.30 (3H, t, J = 6.9). Physical properties: Crystal (melting point: 89-90 ° C).

[0758]

Working Example 476 2-Chlorobenzoic acid = 1
-Ethoxymethoxy-5,5-dimethyl-2-oxo-
3- (2,4-dichlorophenyl) -2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 1)
0-239) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.88-7.80 (1H, m), 7.49-7.2
6 (6H, m), 5.13 (2H, s), 3.89 (2H, q, J = 6.9), 1.59
(6H, s), 1.30 (3H, t, J = 6.9). Physical properties: crystals (melting point: 106-108 ° C).

[0759]

Working Example 477 2-Methoxybenzoic acid =
1-ethoxymethoxy-5,5-dimethyl-2-oxo-3- (2,4-dichlorophenyl) -2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 10-240) ¹ H- NMR (CDCl ₃ ) δ (ppm): 7.84 (1H, dd, J = 6.6, 1.8),
7.56 (1H, m), 7.40-7.21 (3H, s), 7.08-6.94 (2H,
m), 5.12 (2H, s), 3.88 (2H, q, J = 6.9), 3.87 (3H,
s), 1.57 (6H, s), 1.30 (3H, t, J = 6.9). Physical properties: Crystal (melting point: 85-86 ° C).

[0760]

Working Example 478 3-Methoxybenzoic acid =
1-ethoxymethoxy-5,5-dimethyl-2-oxo-3- (2,4-dichlorophenyl) -2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 10-241) ¹ H- NMR (CDCl ₃ ) δ (ppm): 7.67-7.15 (7H, m), 5.13 (2
H, s), 3.90 (2H, q, J = 7.3), 3.84 (3H, s), 1.58 (6
H, s), 1.32 (3H, t, J = 7.3). Physical properties: oil.

[0761]

Working Example 479 4-methoxybenzoic acid =
1-ethoxymethoxy-5,5-dimethyl-2-oxo-3- (2,4-dichlorophenyl) -2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 10-242) ¹ H- NMR (CDCl ₃ ) δ (ppm): 8.07-7.96 (2H, m), 7.40 (1
H, d, J = 8.4), 7.32-7.24 (2H, m), 6.96-6.92 (2H, m),
5.12 (2H, s), 3.90 (2H, q, J = 7.3), 3.88 (3H, s),
1.59 (6H, s), 1.30 (3H, t, J = 7.3). Physical properties: Crystal (melting point: 90-93 ° C).

[0762]

Working Example 480 2-Fluorobenzoic acid =
1-ethoxymethoxy-5,5-dimethyl-2-oxo-3- (2,4-dichlorophenyl) -2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 10-243) ¹ H- NMR (CDCl ₃ ) δ (ppm): 7.94-7.87 (1H, m), 7.67-7.5
7 (1H, m), 7.43 (1H, d, J = 8.4), 7.36-7.14 (4H, m),
5.13 (2H, s), 3.90 (2H, q, J = 7.0), 1.58 (6H, s),
1.30 (3H, t, J = 7.0). Physical properties: oil.

[0763]

Working Example 481 2,4-Dimethoxybenzoic acid = 1-ethoxymethoxy-5,5-dimethyl-2-
Oxo-3- (2,4-dichlorophenyl) -2,5-
Dihydro-1H-pyrrol-4-yl ester (Compound No. 10-244) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.89 (1H, d, J = 8.8), 7.41-
7.22 (3H, m), 6.55-6.46 (3H, m), 5.12 (2H, s), 3.89
(2H, q, J = 7.0), 3.87 (3H, s), 3.85 (3H, s), 1.59
(6H, s), 1.30 (3H, t, J = 7.0). Physical properties: oil.

[0764]

Working Example 482 2,6-Dimethoxybenzoic acid = 1-ethoxymethoxy-5,5-dimethyl-2-
Oxo-3- (2,4-dichlorophenyl) -2,5-
Dihydro-1H-pyrrol-4-yl ester (Compound No. 10-245) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.44-7.26 (3H, m), 6.54 (2
H, d, J = 8.4), 5.12 (2H, s), 3.90 (2H, t, J = 7.3), 3.
74 (6H, s), 1.59 (6H, s), 1.30 (3H, t, J = 7.3). Physical properties: oil.

[0765]

Working Example 483 3,5-Dimethoxybenzoic acid = 1-ethoxymethoxy-5,5-dimethyl-2-
Oxo-3- (2,4-dichlorophenyl) -2,5-
Dihydro-1H-pyrrol-4-yl ester (Compound No. 10-246) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.43-7.25 (3H, m), 7.15 (2
H, d, J = 2.2), 5.13 (2H, s), 3.90 (2H, q, J = 7.0), 3.
82 (6H, s), 1.60 (6H, s), 1.30 (3H, t, J = 7.0). Physical properties: amorphous.

[0766]

Working Example 484 2,4-Difluorobenzoic acid = 1-ethoxymethoxy-5,5-dimethyl-2
-Oxo-3- (2,4-dichlorophenyl) -2,5
-Dihydro-1H-pyrrol-4-yl ester (Compound No. 10-247) ¹ H-NMR (CDCl ₃ ) δ (ppm): 8.01-7.89 (1H, m), 7.42 (1
H, d, J = 8.4), 7.35-7.26 (2H, m), 7.03-6.88 (2H, m),
5.12 (2H, s), 3.90 (2H, q, J = 7.0), 1.57 (6H, s),
1.30 (3H, t, J = 7.0). Physical properties: oil.

[0767]

Working Example 485 Nicotinic Acid 1-ethoxymethoxy-5,5-dimethyl-2-oxo-3- (2
4-Dichlorophenyl) -2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 10-24)
8) ¹ H-NMR (CDCl ₃ ) δ (ppm): 9.25 (1H, d, J = 1.5), 8.86
(1H, dd, J = 4.8, 1.8), 8.28 (1H, dt, J = 8.1, 1.8),
7.49-7.27 (4H, m), 5.13 (2H, s), 3.90 (2H, q, J = 7.
0), 1.59 (6H, s), 1.31 (3H, t, J = 7.0). Physical properties: oil.

[0768]

Working Example 486 2-methoxynicotinic acid =
1-ethoxymethoxy-5,5-dimethyl-2-oxo-3- (2,4-dichlorophenyl) -2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 10-249) ¹ H- NMR (CDCl ₃ ) δ (ppm): 8.39 (1H, dd, J = 5.1, 2.2),
8.18 (1H, dd, J = 7.7, 1.8), 7.43-7.25 (3H, m), 6.99
(1H, dd, J = 7.7, 5.1), 5.13 (2H, s), 4.02 (3H, s),
3.90 (2H, q, J = 7.0), 1.57 (6H, s), 1.30 (3H, t, J
= 7.0). Physical properties: oil.

[0769]

Working Example 487 Cyclopropanecarboxylic acid = 5,5-dimethyl-1-methoxyethoxy-2
-Oxo-3- (2,4-dichlorophenyl) -2,5
-Dihydro-1H-pyrrol-4-yl ester (Compound No. 10-250) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.40-7.24 (3H, m), 4.30 (2
H, t, J = 3.2), 3.71 (2H, t, J = 3.2), 3.43 (3H, s), 1.
82-1.69 (1H, m), 1.51 (6H, s), 1.06-0.95 (4H, m). Physical properties: Crystal (melting point: 85-86 ° C).

[0770]

Example 488 Cyclobutanecarboxylic acid = 5,5-dimethyl-1-methoxyethoxy-2-oxo-3- (2,4-dichlorophenyl) -2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 10-251) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.41-7.25 (3H, m), 4.30 (2
H, t, J = 3.2), 3.71 (2H, t, J = 3.2), 3.43 (3H, s), 3.
28 (1H, septet, J = 8.4), 2.33-1.81 (6H, m), 1.49 (6
H, s). Physical properties: oil.

[0771]

Working Example 489 Benzoic acid = 5,5-dimethyl-1-methoxyethoxy-2-oxo-3- (2
4-Dichlorophenyl) -2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 10-25)
2) ¹ H-NMR (CDCl ₃ ) δ (ppm): 8.05-8.00 (2H, m), 7.69-7.2
5 (6H, m), 4.36-4.31 (2H, m), 3.75-3.70 (2H, m),
3.44 (3H, s), 1.59 (6H, s). Physical properties: amorphous.

[0772]

Example 490 2-Methylbenzoic acid =
5,5-Dimethyl-1-methoxyethoxy-2-oxo-3- (2,4-dichlorophenyl) -2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 10-253) ¹ H- NMR (CDCl ₃ ) δ (ppm): 7.99 (1H, d, J = 7.7), 7.53-
7.25 (6H, m), 4.36-4.31 (2H, m), 3.75-3.70 (2H, m),
3.44 (3H, s), 2.44 (3H, s), 1.59 (6H, s). Physical properties: Crystal (melting point: 89-90 ° C).

[0773]

Working Example 491 2-methoxybenzoic acid =
5,5-dimethyl-1-methoxyethoxy-2-oxo-3- (2,4-dichlorophenyl) -2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 10-254) ¹ H- NMR (CDCl ₃ ) δ (ppm): 7.87-7.81 (1H, m), 7.60-7.5
1 (1H, m), 7.42-7.24 (3H, m), 7.08-6.97 (2H, m),
4.35-4.31 (2H, m), 3.87 (3H, s), 3.75-3.70 (2H,
m), 3.44 (3H, s), 1.58 (6H, s). Physical properties: oil.

[0774]

Working Example 492 Nicotinic acid = 5,5-dimethyl-1-methoxyethoxy-2-oxo-3- (2
4-Dichlorophenyl) -2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 10-25)
5) ¹ H-NMR (CDCl ₃ ) δ (ppm): 9.24 (1H, d, J = 1.8), 8.86
(1H, dd, J = 4.8, 1.5), 8.27 (1H, dt, H = 7.7, 1.8),
7.49-7.27 (4H, m), 4.37-4.32 (2H, m), 3.75-3.71 (2
H, m), 3.45 (3H, s), 1.60 (6H, s). Physical properties: oil.

[0775]

Working Example 493 Cyclopropanecarboxylic acid = 5,5-dimethyl-1-methoxymethoxy-2-
Oxo-3- (2-chlorophenyl) -2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 10-256) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.42-7.24 (5H , m), 5.05 (2
H, s), 3.62 (3H, s), 1.76-1.65 (1H, m), 1.51 (6H,
s), 1.04-0.90 (4H, m). Physical properties: oil.

[0776]

Example 494 1-Methylcyclopropanecarboxylic acid = 5,5-dimethyl-1-methoxymethoxy-2-oxo-3- (2-chlorophenyl) -2,
5-Dihydro-1H-pyrrol-4-yl ester (Compound No. 10-257) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.40-7.25 (5H, m), 5.05 (2
H, s), 3.62 (3H, s), 1.49 (6H, s), 1.30 (3H, s),
1.26-1.14 (2H, m), 0.86-0.75 (2H, m). Physical properties: oil.

[0777]

Working Example 495 2-Methoxybenzoic acid =
5,5-dimethyl-1-methoxymethoxy-2-oxo-3- (2-chlorophenyl) -2,5-dihydro-1
H-pyrrol-4-yl ester (Compound No. 10-
258) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.83 (1H, dd, J = 8.0, 1.8),
7.58-7.19 (5H, m), 7.03-6.95 (2H, m), 5.08 (2H,
s), 3.86 (3H, s), 3.64 (3H, s), 1.57 (6H, s). Physical properties: oil.

[0778]

Working Example 496 Cyclopropanecarboxylic acid = 1-ethoxymethoxy-5,5-dimethyl-2-
Oxo-3- (2-chlorophenyl) -2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 10-259) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.40-7.22 (4H , m), 5.10 (2
H, s), 3.88 (2H, t, J = 7.0), 1.79-1.66 (1H, m), 1.5
1 (6H, s), 1.29 (3H, t, J = 7.0), 1.04-0.89 (4H,
m). Physical properties: crystals (melting point: 97-99 ° C).

[0779]

Working Example 497 1-Methylcyclopropanecarboxylic acid = 1-ethoxymethoxy-5,5-dimethyl-2-oxo-3- (2-chlorophenyl) -2,
5-Dihydro-1H-pyrrol-4-yl ester (Compound No. 10-260) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.40-7.24 (4H, m), 5.10 (2
H, s), 3.88 (2H, q, J = 7.3), 1.49 (6H, s), 1.30 (3
H, s), 1.29 (3H, t, J = 7.3), 1.23-1.18 (2H, m), 0.80
-0.74 (2H, m). Physical properties: crystals (melting point: 94-96 ° C).

[0780]

Working Example 498 1-cyanocyclopropanecarboxylic acid = 1-ethoxymethoxy-5,5-dimethyl-2-oxo-3- (2-chlorophenyl) -2,
5-Dihydro-1H-pyrrol-4-yl ester (Compound No. 10-261) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.44-7.28 (4H, m), 5.11 (2
H, s), 3.89 (2H, t, J = 7.0), 1.78-1.54 (4H, m), 1.5
7 (6H, s), 1.30 (3H, t, J = 7.0). Physical properties: oil.

[0781]

Example 499 Cyclobutanecarboxylic acid = 1-ethoxymethoxy-5,5-dimethyl-2-oxo-3- (2-chlorophenyl) -2,5-dihydro-1H-pyrrol-4-yl ester (compound Number 1
0-262) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.40-7.22 (4H, m), 5.11 (2
H, s), 3.88 (2H, t, J = 7.0), 3.34-3.13 (1H, m), 2.3
6-1.75 (6H, m), 1.49 (6H, s), 1.29 (3H, t, J = 7.
0). Physical properties: Crystal (melting point: 103-105 ° C).

[0782]

Example 500 Cyclopentanecarboxylic acid 1-ethoxymethoxy-5,5-dimethyl-2-
Oxo-3- (2-chlorophenyl) -2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 10-263) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.40-7.22 (4H , m), 5.11 (2
H, s), 3.88 (2H, t, J = 7.0), 2.95-2.75 (1H, m), 1.9
5-1.54 (8H, m), 1.50 (6H, s), 1.29 (3H, t, J = 7.
0). Physical properties: crystals (melting point: 107-108 ° C).

[0783]

Working Example 501 3-Methyloxetane-3-carboxylic acid = 1-ethoxymethoxy-5,5-dimethyl-2-oxo-3- (2-chlorophenyl)-
2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 10-264) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.41-7.27 (4H, m), 5.11 (2
H, s), 4.83 (2H, d, J = 6.2), 4.38 (2H, d, J = 6.2),
3.89 (2H, d, J = 7.0), 1.60 (3H, s), 1.52 (6H, s),
1.30 (3H, t, J = 7.0). Physical properties: crystals (melting point: 126-129 ° C).

[0784]

Working Example 502 2-Methylbenzoic Acid = 1
-Ethoxymethoxy-5,5-dimethyl-2-oxo-
3- (2-chlorophenyl) -2,5-dihydro-1H
-Pyrrole-4-yl ester (Compound No. 10-2)
65) ¹ H-NMR (CDCl ₃ ) δ (ppm): 8.01-7.97 (1H, m), 7.50-7.1
8 (7H, m), 5.14 (2H, s), 3.90 (2H, t, J = 7.0), 2.64
(3H, s), 1.58 (6H, s), 1.30 (3H, t, J = 7.0). Physical properties: oil.

[0785]

Working Example 503 2-methoxybenzoic acid =
1-ethoxymethoxy-5,5-dimethyl-2-oxo-3- (2-chlorophenyl) -2,5-dihydro-1
H-pyrrol-4-yl ester (Compound No. 10-
266) ¹ H-NMR (CDCl ₃ ) δ (ppm): 8.02 (1H, dd, J = 7.7, 1.8),
7.82 (1H, dd, J = 7.7, 1.8), 7.60-6.95 (6H, m), 5.13
(2H, s), 3.90 (2H, q, J = 7.0), 3.86 (3H, s), 3.85
(3H, s), 1.58 (6H, s), 1.30 (3H, t, J = 7.0). Physical properties: oil.

[0786]

Working Example 504 Thiophosphonic Acid = O, O ′
-Diethyl ester = O "-[1-ethoxymethyl-
5,5-Dimethyl-2-oxo-3- (2-chlorophenyl) -2,5-dihydro-1H-pyrrol-4-yl] ester (Compound No. 10-267) ¹ H-NMR (CDCl ₃ ) δ ( ppm): 7.46-7.24 (4H, m), 5.09 (2
H, s), 4.12-3.45 (6H, m), 1.55 (6H, s), 1.29 (6H,
t, J = 7.0), 1.08 (3H, brd.t, J = 7.0). Physical properties: oil.

[0787]

Example 505 Cyclopropanecarboxylic acid = 5,5-dimethyl-1-methoxyethoxy-2-
Oxo-3- (2-chlorophenyl) -2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 10-268) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.42-7.21 (4H , m), 4.33-4.2
8 (2H, m), 3.74-3.69 (2H, m), 3.43 (3H, s), 1.79-
1.66 (1H, m), 1.52 (6H, s), 1.06-0.93 (4H, m). Physical properties: oil.

[0788]

Working Example 506 1-Methylcyclopropanecarboxylic acid = 5,5-dimethyl-1-methoxyethoxy-2-oxo-3- (2-chlorophenyl) -2,
5-Dihydro-1H-pyrrol-4-yl ester (Compound No. 10-269) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.40-7.25 (4H, m), 4.33-4.2
8 (2H, m), 3.74-3.69 (2H, m), 3.43 (3H, s), 1.50
(6H, s), 1.29 (3H, s), 1.23-1.18 (2H, m), 0.80-0.7
4 (2H, m). Physical properties: oil.

[0789]

Working Example 507 1-cyanocyclopropanecarboxylic acid = 5,5-dimethyl-1-methoxyethoxy-2-oxo-3- (2-chlorophenyl) -2,
5-Dihydro-1H-pyrrol-4-yl ester (Compound No. 10-270) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.44-7.25 (4H, m), 4.34-4.3
0 (2H, m), 3.74-3.69 (2H, m), 3.44 (3H, s), 1.77-
1.51 (4H, m), 1.58 (6H, s). Physical properties: oil.

[0790]

Working Example 508 Cyclobutanecarboxylic acid = 5,5-dimethyl-1-methoxyethoxy-2-oxo-3- (2-chlorophenyl) -2,5-dihydro-1H-pyrrol-4-yl ester (compound Number 1
0-271) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.40-7.25 (4H, m), 4.33-4.2
8 (2H, m), 3.74-3.69 (2H, m), 3.43 (3H, s), 3.35-
3.15 (1H, m), 2.35-1.75 (6H, m), 1.50 (6H, s). Physical properties: oil.

[0791]

Working Example 509 Cyclopentanecarboxylic acid = 5,5-dimethyl-1-methoxyethoxy-2-
Oxo-3- (2-chlorophenyl) -2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 10-272) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.40-7.22 (4H , m), 4.33-4.2
8 (2H, m), 3.74-3.69 (2H, m), 3.43 (3H, s), 2.89-
2.78 (1H, m), 1.92-1.54 (8H, m), 1.50 (6H, s). Physical properties: oil.

[0792]

Example 510 3-Methyloxetane-3-carboxylic acid = 5,5-dimethyl-1-methoxyethoxy-2-oxo-3- (2-chlorophenyl)-
2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 10-273) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.41-7.25 (4H, m), 4.82 (2
H, d, J = 6.2), 4.38 (2H, d, J = 6.2), 4.34-4.30 (2H,
m), 3.74-3.69 (2H, m), 3.44 (3H, s), 1.59 (3H, s),
1.52 (6H, s). Physical properties: oil.

[0793]

Example 511 2-methylbenzoic acid =
5,5-dimethyl-1-methoxyethoxy-2-oxo-3- (2-chlorophenyl) -2,5-dihydro-1
H-pyrrol-4-yl ester (Compound No. 10-
274) ¹ H-NMR (CDCl ₃ ) δ (ppm): 8.01-7.97 (1H, m), 7.51-7.4
2 (2H, m), 7.35-7.19 (5H, m), 4.37-4.32 (2H, m),
3.76-3.72 (2H, m), 3.45 (3H, s), 2.41 (3H, s), 1.5
9 (6H, s). Physical properties: oil.

[0794]

Example 512 2-methoxybenzoic acid =
5,5-dimethyl-1-methoxyethoxy-2-oxo-3- (2-chlorophenyl) -2,5-dihydro-1
H-pyrrol-4-yl ester (Compound No. 10-
275) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.85-7.80 (1H, m), 7.57-7.2
1 (5H, m), 7.02-6.95 (3H, m), 4.36-4.31 (2H, m),
3.85 (3H, s), 3.76-3.71 (2H, m), 3.44 (3H, s), 1.5
8 (6H, s). Physical properties: oil.

[0795]

Working Example 513 5- (2- [1,3] Dioxane-2
-Ylethyl) -4-hydroxy-5-methyl-1-methoxymethoxy-2-oxo-3- (2,6-dimethylphenyl) -2,5-dihydro-1H-pyrrole (Compound No. 11-1) ¹ H -NMR (CDCl ₃ ) δ (ppm): 7.18-7.02 (3H, m), 5.00 (2
H, ABq, J = 7.3), 4.55-4.47 (1H, m), 4.08-3.95 (2H,
m), 3.77-3.60 (2H, m), 3.58 (3H, s), 2.20 (3H, s),
2.17 (3H, s), 2.15-1.20 (6H, m), 1.53 (3H, s). Physical properties: oil.

[0796]

Example 514 4-Hydroxy-5-methyl-1-methoxymethoxy-5- (tetrahydrofuran-2-ylmethyl) -2-oxo-3- (2,6-dimethylphenyl) -2,5-dihydro-1H -Pyrrole (Compound No. 11-2) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.15-7.00 (3H, m), 5.04 (2
H, ABq, J = 7.7), 4.30-4.13 (1H, m), 4.05-3.87 (2H,
m), 3.55 (3H, s), 2.60-1.50 (6H, m), 2.20 (6H, s),
1.61 (3H, s). Physical properties: oil.

[0797]

Example 515 5-Allyl-4-hydroxy-5-methyl-1-methoxymethoxy-2-oxo-3- (2
6-dimethylphenyl) -2,5-dihydro-1H-pyrrole (Compound No. 11-3) ¹ H-NMR (DMSO-d ₆ ) δ (ppm): 11.43 (1H, s), 7.16-6.98
(3H, s), 5.76-5.56 (1H, m), 5.19-5.03 (2H, m), 4.9
0 (2H, ABq, J = 7.3), 3.48 (3H, s), 2.56 (2H, m), 2.0
7 (6H, s), 1.43 (3H, s). Physical properties: crystals (melting point: 136-139 ° C).

[0798]

Example 516: 5-benzyl-4-hydroxy-5
Methyl-1-methoxymethoxy-2-oxo-3-
(2,6-dimethylphenyl) -2,5-dihydro-1
H-pyrrole (Compound No. 11-4) ¹ H-NMR (DMSO-d ₆ ) δ (ppm): 11.50 (1H, s), 7.38-6.79
(8H, m), 5.05 (2H, ABq, J = 7.3), 3.56 (3H, s), 3.09
(2H, ABq, J = 13.5), 2.02 (3H, s), 1.55 (3H, s), 1.1
8 (3H, s). Physical properties: crystals (melting point: 167-168 ° C).

[0799]

Example 517 5-Cyclohexylmethyl-4-hydroxy-5-methyl-1-methoxymethoxy-2-oxo-3- (2,6-dimethylphenyl) -2,5-dihydro-1H-pyrrole (compound No. 11-5) ¹ H-NMR (DMSO-d ₆ ) δ (ppm): 11.42 (1H, s), 7.17-7.01
(3H, m), 4.88 (2H, ABq, J = 7.6), 3.46 (3H, s), 2.26
(1H, t, J = 4.7), 2.13 (3H, s), 2.07 (3H, s), 1.85-
0.80 (15H, m). Physical properties: crystals (melting point: 174-176 ° C).

[0800]

Example 518: 4-Hydroxy-5-methyl-1-methoxymethoxy-5-phenethyl-2-oxo-3-
(2,6-dimethylphenyl) -2,5-dihydro-1
H-pyrrole (Compound No. 11-6) ¹ H-NMR (DMSO-d ₆ ) δ (ppm): 11.60 (1H, s), 7.33-7.05
(8H, m), 4.97 (2H, ABq, J = 7.6), 3.48 (3H, s), 2.16
(3H, s), 2.11 (3H, s), 2.78-1.97 (4H, m), 1.44 (3
H, s). Physical properties: crystals (melting point: 194-195 ° C).

[0801]

EXAMPLE 519 4-Hydroxy-5-methyl-5
(2-methoxyethyl) -1-methoxymethoxy-2-
Oxo-3- (2,6-dimethylphenyl) -2,5-
Dihydro-1H-pyrrole (Compound No. 11-7) ¹ H-NMR (DMSO-d ₆ ) δ (ppm): 11.53 (1H, s), 7.14-7.02
(3H, m), 4.89 (2H, ABq, J = 7.3), 3.47 (3H, s), 3.46
-3.25 (2H, m), 3.18 (3H, s), 2.22-2.00 (8H, m), 1.4
2 (3H, s). Physical properties: Crystal (melting point: 105.0-105.5 ° C).

[0802]

Example 520 4-Hydroxy-8-oxa-3-
(2,6-dimethylphenyl) -1-azaspiro [4.
5] Decane-3-en-2-one (Compound No. 11-
8) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.22-7.07 (3H, m), 6.92 (1
H, s), 5.05 (2H, s), 4.03-3.98 (4H, m), 3.62 (3H,
s), 2.49-2.37 (2H, m), 2.18 (6H, s), 1.90-1.75 (2
H, m). Physical properties: crystals (melting point: 177-180 ° C).

[0803]

Working Example 521 2-Methylbenzoic acid = 8
-Oxa-3- (2,6-dimethylphenyl) -1-azaspiro [4.5] decane-3-en-2-one-4-
Il = ester (Compound No. 11-9) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.54-7.45 (2H, m), 7.11-6.9
0 (5H, m), 5.13 (2H, s), 4.10-3.87 (4H, m), 3.84
(3H, s), 3.66 (3H, s), 2.51-2.38 (2H, m), 2.26 (6
H, s), 2.01-1.94 (2H, m). Physical properties: crystals (melting point: 129-130 ° C).

[0804]

Example 522 5- (4-Chlorobenzyl) -4-hydroxy-5-methyl-1-ethoxymethoxy-2-oxo-3- (2,6-dimethylphenyl) -2,5-dihydro-1H- Pyrrole (Compound No. 11-10) ¹ H-NMR (DMSO-d ₆ ) δ (ppm): 7.34 (2H, d, J = 8.4), 7.26
(2H, d, J = 8.4), 7.06-6.84 (3H, m), 5.07 (2H, ABq,
J = 7.7), 3.95-3.71 (2H, m), 3.07 (2H, ABq, J = 13.
5), 2.02 (6H, m), 1.52 (3H, m), 1.23 (3H, t, J = 7.
0). Physical properties: Crystal (melting point: 186-190 ° C).

[0805]

Working Example 523 5- (2-Chlorobenzyl) -4-hydroxy-5-methyl-1-ethoxymethoxy-2-oxo-3- (2,6-dimethylphenyl) -2,5-dihydro-1H- Pyrrole (Compound No. 11-11) ¹ H-NMR (DMSO-d ₆ ) δ (ppm): 11.45 (1H, brd.s), 7.64-
7.59 (1H, m), 7.39-7.32 (1H, m), 7.25-7.15 (2H, m),
7.08-6.87 (3H, m), 5.07 (2H, q, J = 7.3), 3.88-3.74
(2H, m), 3.29 (2H, ABq, J = 14.6), 2.02 (6H, s), 1.
57 (3H, s), 1.18 (3H, t, J = 7.3). Physical properties: crystals (melting point: 130-134 ° C).

[0806]

Example 524 Cyclopropanecarboxylic acid = 1-ethoxymethyl-3- (2,6-dimethylphenyl) -1-azaspiro [4.4] nonan-3-en-2-one-4-yl = ester (Compound No. 11-1
2) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.16-6.99 (3H, m), 5.18 (2
H, s), 3.93 (2H, q, J = 7.0), 3.03-2.86 (2H, m), 2.5
1-2.40 (2H, m), 2.18 (6H, s), 2.03-1.83 (2H, m), 1.
74-1.61 (1H, m), 1.32 (3H, t, J = 7.0), 0.95-0.81 (3
H, m). Physical properties: crystals (melting point: 115-116 ° C).

[0807]

Example 525 5-ethyl-4-hydroxy-5-methyl-1-methoxymethoxy-2-oxo-3- (2
4-Dichlorophenyl) -2,5-dihydro-1H-pyrrole (Compound No. 11-13) ¹ H-NMR (DMSO-d ₆ ) δ (ppm): 11.84 (1H, brd.s), 7.65
(1H, d, J = 2.2), 7.43 (1H, dd, J = 8.4, 2.2), 7.28 (1
H, d, J = 8.4), 4.88 (2H, ABq, J = 7.7), 3.46 (3H, s),
1.79 (2H, q, J = 7.3), 1.39 (3H, s), 0.75 (3H, t, J
= 7.3). Physical properties: crystals (melting point: 122-127 ° C).

[0808]

Example 526 4-Hydroxy-5-methyl-5-
(4-methoxybenzyl) -1-methoxymethoxy-2
-Oxo-3- (2,4-dichlorophenyl) -2,5
-Dihydro-1H-pyrrole (Compound No. 11-14) ¹ H-NMR (DMSO-d ₆ ) δ (ppm): 7.48 (1H, m), 7.29 (1H, d)
d, J = 8.4, 2.6), 7.16 (2H, d, J = 8.8), 6.85-6.72 (3
H, m), 4.97 (2H, ABq, J = 7.7), 3.69 (3H, s), 3.53
(3H, s), 2.99 (2H, ABq, J = 13.6), 1.47 (3H, s). Physical properties: oil.

[0809]

Example 527 4-Hydroxy-5-methyl-5
(3-methylbenzyl) -1-methoxymethoxy-2-
Oxo-3- (2,4-dichlorophenyl) -2,5-
Dihydro-1H-pyrrole (Compound No. 11-15) ¹ H-NMR (DMSO-d ₆ ) δ (ppm): 7.51 (1H, d, J = 2.2), 7.31
(1H, dd, J = 8.4, 2.2), 7.13-6.68 (5H, m), 4.98 (2H,
ABq, J = 7.3), 3.54 (3H, s), 3.05 (2H, ABq, J = 13.6),
2.21 (3H, s), 1.51 (3H, s). Physical properties: crystals (melting point: 128-132 ° C).

[0810]

Example 528 4-Hydroxy-5-methyl-5
(3-methoxybenzyl) -1-methoxymethoxy-2
-Oxo-3- (2,4-dichlorophenyl) -2,5
-Dihydro-1H-pyrrole (Compound No. 11-16) ¹ H-NMR (DMSO-d ₆ ) δ (ppm): 7.51 (1H, d, J = 1.8), 7.30
(1H, dd, J = 8.8, 2.2), 7.11 (1H, t, J = 8.8), 6.86-6.
71 (4H, m), 5.00 (2H, ABq, J = 7.7), 3.67 (3H, s),
3.54 (3H, s), 3.06 (2H, ABq, J = 13.6), 1.52 (3H,
s). Physical properties: oil.

[0811]

Example 529 1-ethoxymethoxy-5-ethyl-
4-hydroxy-5-methyl-2-oxo-3- (2,
4-Dichlorophenyl) -2,5-dihydro-1H-pyrrole (Compound No. 11-17) ¹ H-NMR (DMSO-d ₆ ) δ (ppm): 11.82 (1H, brd.s), 7.65
(1H, d, J = 2.2), 7.43 (1H, dd, J = 8.4, 2.2), 7.28 (1
H, d, J = 8.4), 4.92 (2H, ABq, J = 8.4), 3.74 (2H, q,
J = 7.0), 1.79 (2H, q, J = 7.3), 1.39 (3H, s), 1.17 (3
H, t, J = 7.0), 0.75 (3H, t, J = 7.3). Physical properties: crystals (melting point: 145-148 ° C).

[0812]

Example 530 2-methoxybenzoic acid =
1-ethoxymethoxy-5-ethyl-5-methyl-2-
Oxo-3- (2,4-dichlorophenyl) -2,5-
Dihydro-1H-pyrrol-4-yl ester (Compound No. 11-18) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.83 (1H, dd, J = 8.0, 1.8),
7.60-7.51 (1H, m), 7.43 (1H, d, J = 8.4), 7.34 (1H,
d, J = 1.8), 7.27 (1H, dd, J = 8.0, 1.8), 7.05-6.97 (2
H, m), 5.12 (2H, s), 3.87 (2H, q, J = 7.0), 3.87 (3
H, s), 2.08-1.73 (2H, m), 1.56 (3H, s), 1.29 (3H,
t, J = 7.0), 0.94 (3H, t, J = 7.0). Physical properties: oil.

[0813]

Working Example 531 1-Ethoxymethoxy-5-isopropyl-4-hydroxy-5-methyl-2-oxo-3-
(2,4-dichlorophenyl) -2,5-dihydro-1
H-pyrrole (Compound No. 11-19) ¹ H-NMR (DMSO-d ₆ ) δ (ppm): 11.74 (1H, brd.s), 7.64
(1H, d, J = 1.8), 7.42 (1H, dd, J = 8.0, 1.8), 7.27 (1
(H, d, J = 8.0), 4.95 (2H, s), 3.80-3.68 (2H, m), 2.2
1-2.08 (1H, m), 1.43 (3H, s), 1.15 (3H, t, J = 7.3),
1.03 (3H, d, J = 7.3), 0.91 (3H, d, J = 7.3). Physical properties: gum-like.

[0814]

Working Example 532 1-Ethoxymethyl-4-hydroxy-3- (2,4-dichlorophenyl) -1-azaspiro [4.4] nonan-3-en-2-one (Compound No. 1)
1-20) ¹ H-NMR (DMSO-d ₆ ) δ (ppm): 7.64 (1H, d, J = 2.2), 7.41
(1H, dd, J = 8.0, 2.2), 7.28 (1H, d, J = 8.0), 5.02 (2
H, s), 3.82 (2H, q, J = 7.3), 2.75-2.55 (2H, m), 2.45
-2.25 (2H, m), 2.05-1.70 (2H, m), 1.21 (3H, t, J =
7.0). Physical properties: crystals (melting point: 143-148 ° C).

[0815]

Working Example 533 1,4-Bis (ethoxymethyl) -3
-(2,4-dichlorophenyl) -1-azaspiro [4.4] nonan-3-en-2-one (Compound No. 1
1-21) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.44-7.42 (1H, m), 7.30-7.2
1 (2H, m), 5.14 (2H, s), 4.97 (2H, ABq, J = 5.5), 3.
99-3.85 (2H, m), 3.73-3.62 (2H, m), 2.98-2.78 (2H, m
m), 2.55-2.35 (2H, m), 2.13-1.78 (2H, m), 1.31 (3
H, t, J = 7.0), 1.19 (3H, t, J = 7.0). Physical properties: Crystal (melting point: 98-103 ° C).

[0816]

Example 534 1-ethoxymethoxy-5- (2-chlorobenzyl) -4-hydroxy-5-methyl-2-oxo-3- (2,4-dichlorophenyl) -2,5-dihydro-1H-pyrrole (Compound No. 11-22) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.53-7.17 (7H, m), 5.02 (2
H, ABq, J = 7.3), 3.79 (2H, q, J = 7.0), 3.26 (2H, AB
q, J = 14.2), 1.53 (3H, s), 1.17 (3H, t, J = 7.0). Physical properties: oil.

[0817]

Example 535 1-ethoxymethoxy-5- (3-chlorobenzyl) -4-hydroxy-5-methyl-2-oxo-3- (2,4-dichlorophenyl) -2,5-dihydro-1H-pyrrole (Compound No. 11-23) ¹ H-NMR (DMSO-d ₆ ) δ (ppm): 7.53 (1H, d, J = 1.8), 7.36
-7.24 (6H, m), 5.05 (2H, ABq, J = 7.7), 3.92-3.72 (2
H, m), 3.11 (2H, ABq, J = 13.9), 1.53 (3H, s), 1.22
(3H, t, J = 7.0). Physical properties: oil.

[0818]

Example 536 1-ethoxymethoxy-5- (4-chlorobenzyl) -4-hydroxy-5-methyl-2-oxo-3- (2,4-dichlorophenyl) -2,5-dihydro-1H-pyrrole (Compound No. 11-24) ¹ H-NMR (DMSO-d ₆ ) δ (ppm): 7.51 (1H, d, J = 2.2), 7.34
-7.13 (6H, m), 6.80 (1H, brd.s), 5.04 (2H, ABq, J =
7.7), 3.90-3.73 (2H, m), 3.08 (2H, ABq, J = 17.0),
1.51 (3H, s), 1.22 (3H, t, J = 7.0). Physical properties: oil.

[0819]

Working Example 537 2-Methoxybenzoic acid =
1-ethoxymethoxy-5- (4-chlorobenzyl)-
5-Methyl-2-oxo-3- (2,4-dichlorophenyl) -2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 11-25) ¹ H-NMR (CDCl ₃ ) δ ( ppm): 7.73 (1H, dd, J = 8.0, 1.8),
7.62-7.53 (1H, m), 7.31-7.00 (9H, m), 5.26 (2H,
s), 3.93 (2H, q, J = 7.0), 3.91 (3H, s), 3.35 (1H,
d, J = 13.9), 3.02 (1H, d, J = 13.9), 1.58 (3H, s), 1.
33 (3H, t, J = 7.0). Physical properties: oil.

[0820]

Example 538 1-ethoxymethoxy-4-hydroxy-5-methyl-5- (2-methylbenzyl) -2-oxo-3- (2,4-dichlorophenyl) -2,5-dihydro-1H-pyrrole (Compound No. 11-26) ¹ H-NMR (DMSO-d ₆ ) δ (ppm): 7.51 (1H, d, J = 2.2), 7.42
-7.27 (2H, m), 7.09-6.96 (4H, m), 5.02 (2H, ABq, J
= 7.3), 3.80 (2H, q, J = 7.0), 2.33 (3H, s), 1.54 (3
H, s), 1.18 (3H, t, J = 7.0). Physical properties: crystals (melting point: 137-141 ° C).

[0821]

Working Example 539 1-Ethoxymethoxy-4-hydroxy-5-methyl-5- (3-methylbenzyl) -2-oxo-3- (2,4-dichlorophenyl) -2,5-dihydro-1H-pyrrole (Compound No. 11-27) ¹ H-NMR (DMSO-d ₆ ) δ (ppm): 7.50 (1H, d, J = 2.2), 7.30
(1H, dd, J = 8.4, 2.2), 7.13-6.68 (5H, m), 5.02 (2H,
ABq, J = 7.3), 3.99-3.76 (2H, m), 3.04 (2H, ABq, J = 1
3.6), 2.21 (3H, s), 1.50 (3H, s), 1.21 (3H, t, J =
7.3). Physical properties: oil.

[0822]

Example 540 1-ethoxymethoxy-4-hydroxy-5-methyl-5- (4-methoxybenzyl) -2-
Oxo-3- (2,4-dichlorophenyl) -2,5-
Dihydro-1H-pyrrole (Compound No. 11-28) ¹ H-NMR (DMSO-d ₆ ) δ (ppm): 7.48 (1H, d, J = 2.2), 7.29
(1H, dd, J = 8.0, 2.2), 7.17 (2H, d, J = 8.8), 6.77-6.
72 (3H, m), 5.01 (2H, ABq, J = 7.7), 3.89-3.73 (2H,
m), 3.69 (3H, s), 3.00 (2H, ABq, J = 13.9), 1.47 (3
H, s), 1.21 (3H, t, J = 7.0). Physical properties: Crystal (melting point: 73-77 ° C).

[0823]

Working Example 541 Ethyl carbonate = ester = 1-ethoxymethoxy-5-methyl-5- (4-methoxybenzyl) -2-oxo-3- (2,4-dichlorophenyl)
-2,5-dihydro-1H-pyrrol-4-yl ester (Compound No. 11-29) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.45-7.28 (5H, m), 6.90 (2
H, d, J = 8.8), 4.84 (2H, ABq, J = 7.3), 3.86-3.47 (8H,
m), 1.97 (3H, s), 1.06 (3H, t, J = 7.0). Physical properties: oil.

[0824]

Working Example 542 3- (2,6-Dimethylphenyl)-
4-Hydroxy-1-methoxy-8-methoxymethoxy-1-azaspiro [4,5] decane-3-en-2-one (Compound No. 11-30) ¹ H-NMR (CDCl ₃ ) δ (ppm): 11.42 (1H, s), 7.15-7.04 (3
H, m), 4.64 (2H, s), 3.80 (3H, s), 3.80-3.68 (1H,
m), 3.28 (3H, s), 2.08 (6H, s), 2.10-1.78 (8H,
m). Physical properties: amorphous.

[0825]

Working Example 543 Cyclopropanecarboxylic acid = 3- (2,6-dimethylphenyl) -1-methoxy-8-methoxymethoxy-1-azaspiro [4,5]
Decane-3-en-2-one-4-yl ester (Compound No. 11-31) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.16-7.00 (3H, m), 4.74, 4.
72 (2H, s, s), 4.03, 4.00 (3H, s, s), 3.88-3.72 (1
H, m), 3.42, 3.40 (3H, s, s), 2.20 (6H, s), 2.25-1.
50 (9H, m), 0.86-0.71 (4H, m). Physical properties: amorphous.

[0826]

Working Example 544 8-ethoxymethoxy-3- (2,6
-Dimethylphenyl) -4-hydroxy-1-methoxy-1-azaspiro [4,5] decane-3-en-2-one (Compound No. 11-32) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.77 (1H, brd.s), 7.19-7.03
(3H, m), 4.13 (2H, brd.s), 3.96, 3.92 (3H, s, s),
3.75-3.60 (1H, m), 3.38 (2H, q, J = 7.0), 2.17 (6H,
s), 2.17-1.85 (8H, m), 1.16 (3H, t, J = 7.0). Physical properties: amorphous.

[0827]

Example 545: Cyclopropanecarboxylic acid = 8-ethoxymethoxy-3- (2,6-dimethylphenyl) -1-methoxy-1-azaspiro [4,5]
Decane-3-en-2-one-4-yl ester (Compound No. 11-36) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.15-7.00 (3H, m), 4.77 (2
H, s), 4.00 (3H, s), 3.88-3.75 (1H, m), 3.64 (2H,
q, J = 7.0), 2.20 (6H, s), 2.19-1.53 (9H, m), 1.24
(3H, t, J = 7.0), 0.89-0.76 (4H, m). Physical properties: oil.

[0828]

Embodiment 546 Acetic acid = 3- (2,6
-Dimethylphenyl) -1-methoxy-8- (N-methoxyimino) -1-azaspiro [4,5] decane-3-
En-2-one-4-yl ester (Compound No. 11
−38) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.15-6.98 (3H, m), 4.03 (3
H, s), 3.87 (3H, s), 2.87-2.44 (4H, m), 2.30-1.95
(4H, m), 2.20 (6H, s), 2.00 (3H, s). Physical properties: Crystal (melting point: 156-160 ° C).

[0829]

EXAMPLE 547 Propionic acid = 3- (2,
6-dimethylphenyl) -1-methoxy-8- (N-methoxyimino) -1-azaspiro [4,5] decane-3
-En-2-one-4-yl = ester (Compound No. 1
1-39) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.15-6.98 (3H, m), 4.03 (3
H, s), 3.87 (3H, s), 2.95-2.45 (4H, m), 2.26 (2H,
q, J = 7.7), 2.35-2.00 (4H, m), 2.20 (6H, s), 0.92
(3H, t, J = 7.7). Physical properties: crystals (melting point: 74-76 ° C).

[0830]

Example 548 Cyclopropanecarboxylic acid = 3- (2,6-dimethylphenyl) -1-methoxy-8- (N-methoxyimino) -1-azaspiro [4,5] decane-3-ene-2 -On-4-yl ester (Compound No. 11-41) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.16-7.00 (3H, m), 4.03 (3
H, s), 3.88 (3H, s), 2.97-2.47 (4H, m), 2.34-1.98
(4H, m), 2.20 (6H, s), 1.64-1.50 (1H, m), 0.90-0.8
0 (2H, m), 0.78-0.68 (2H, m). Physical properties: oil.

[0831]

Example 549 8,8-Ethylenedioxy-4-hydroxy-1-methoxy-3- (2,6-dimethylphenyl) -1-azaspiro [4,5] decane-3-en-2
-One (Compound No. 11-42) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.78 (1H, brd.s), 7.19-7.04
(3H, m), 3.95 (3H, s), 3.87 (2H, t, J = 6.2), 3.33
(2H, t, J = 6.2), 2.50-1.75 (8H, m), 2.04 (6H, s). Physical properties: crystals (melting point: 197-198 ° C).

[0832]

Example 550 Acetic acid = 8,8-ethylenedioxy-1-methoxy-3- (2,6-dimethylphenyl) -1-azaspiro [4,5] decane-3-en-2-one- 4-yl = ester (Compound No. 11-
43) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.16-7.00 (3H, m), 4.03 (3
H, s), 4.02-3.96 (4H, m), 2.20 (6H, s), 2.25-1.84
(8H, m), 2.01 (3H, s). Physical properties: Crystal (melting point: 99-101 ° C).

[0832]

Example 551 Propionic acid = 8,8-ethylenedioxy-1-methoxy-3- (2,6-dimethylphenyl) -1-azaspiro [4,5] decane-3-
En-2-one-4-yl ester (Compound No. 11
−44) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.15-6.99 (3H, m), 4.03 (3
H, s), 4.01-3.96 (4H, m), 2.29 (2H, q, J = 7.4), 2.2
0 (6H, s), 2.23-1.58 (8H, m), 0.94 (3H, t, J = 7.
Four). Physical properties: oil.

[0834]

Working Example 552 2-Methylpropionic Acid =
8,8-ethylenedioxy-1-methoxy-3- (2,
6-dimethylphenyl) -1-azaspiro [4,5] decane-3-en-2-one-4-yl ester (Compound No. 11-45) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.15 -6.98 (3H, m), 4.03 (3
H, s), 4.01-3.98 (4H, m), 2.52 (1H, quintet, J = 7.
0), 2.34-1.83 (8H, m), 2.20 (6H, s), 0.95 (6H, d, J
= 7.0). Physical properties: crystals (melting point: 123-126 ° C).

[0835]

Working Example 553 Cyclopropane carboxylic acid = 8,8-ethylenedioxy-1-methoxy-3-
(2,6-dimethylphenyl) -1-azaspiro [4,
5] Decane-3-en-2-one-4-yl ester (Compound No. 11-46) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.18-6.98 (3H, m), 4.02 (4
(H, d, J = 2.6), 2.19 (6H, s), 2.30-1.82 (9H, m), 0.88
-0.71 (4H, m). Physical properties: crystals (melting point: 130-133 ° C).

[0836]

Working Example 554 3- (2,6-Dimethylphenyl)-
4-hydroxy-1-methoxy-8,8-propylenedioxy-1-azaspiro [4,5] decane-3-ene-
2-one (Compound No. 11-47) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.19-7.05 (3H, m), 4.02, 3.
94 (3H, s, s), 3.93-3.85 (2H, m), 3.35-3.33 (2H,
m), 2.36-1.56 (10H, m), 2.17 (6H, s). Physical properties: crystals (melting point: 185-187 ° C).

[0837]

Embodiment 555 Acetic acid = 3- (2,6
-Dimethylphenyl) -1-methoxy-8,8-propylenedioxy-1-azaspiro [4,5] decane-3-
En-2-one-4-yl ester (Compound No. 11
−48) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.16-7.00 (3H, m), 4.02 (3
H, s), 4.00-3.90 (4H, m), 2.24-1.71 (10H, m), 2.19
(6H, s), 2.00 (3H, s). Physical properties: crystals (melting point: 153-156 ° C).

[0838]

Example 556 Propionic acid = 3- (2,
6-dimethylphenyl) -1-methoxy-8,8-propylenedioxy-1-azaspiro [4,5] decane-3
-En-2-one-4-yl = ester (Compound No. 1
1-49) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.15-7.00 (3H, m), 4.02 (3
H, s), 4.00-3.89 (4H, m), 2.27 (2H, q, J = 7.7), 2.2
0 (6H, s), 2.20-1.71 (10H, m), 0.93 (3H, t, J = 7.
7). Physical properties: gum-like.

[0839]

Working Example 557 Cyclopropanecarboxylic acid 3- (2,6-dimethylphenyl) -1-methoxy-8,8-propylenedioxy-1-azaspiro [4,5] decane-3-en-2-ene On-4-yl ester (Compound No. 11-51) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.15-6.98 (3H, m), 4.02 (3
H, s), 4.00-3.91 (4H, m), 2.19 (6H, s), 2.22-1.50
(11H, m), 0.88-0.72 (4H, m). Physical properties: crystals (melting point: 145-147 ° C).

[0840]

Working Example 558 1,8-Bis (methoxymethoxy)-
3- (2,6-dimethylphenyl) -4-hydroxy-
1-azaspiro [4,5] decane-3-en-2-one (Compound No. 11-52) ¹ H-NMR (DMSO-d ₆ ) δ (ppm): 11.55-11.45 (1H, m), 7.15
-7.04 (3H, m), 4.93, 4.90 (2H, s, s), 4.65, 4.64
(2H, s, s), 3.80-3.50 (1H, m), 3.49, 3.47 (3H, s,
s), 3.29, 3.27 (3H, s, s), 2.45-1.55 (8H, m), 2.08
(6H, s). Physical properties: gum-like.

[0841]

Working Example 559 Cyclopropanecarboxylic acid = 1,8-bis (methoxymethoxy) -3- (2,5
6-dimethylphenyl) -1-azaspiro [4,5] decane-3-en-2-one-4-yl ester (Compound No. 11-53) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.16 -6.96 (3H, m), 5.09, 5.
07 (2H, s, s), 4.72, 4.71 (2H, s, s), 3.95-3.60 (1
H, m), 3.64, 3.61 (3H, s, s), 3.41, 3.40 (3H, s,
s), 2.55-1.50 (9H, m), 2.19 (6H, s), 0.85-0.76 (4
H, m). Physical properties: amorphous.

[0842]

Example 560 8-ethoxymethoxy-3- (2,6
-Dimethylphenyl) -4-hydroxy-1-methoxymethoxy-1-azaspiro [4,5] decane-3-en-2-one (Compound No. 11-54) ¹ H-NMR (CDCl ₃ ) δ (ppm) : 8.17 (1H, brd.s), 7.20-7.04
(3H, m), 5.03, 4.99 (3H, s, s), 4.00 (2H, s), 3.6
1, 3.57 (3H, s), 3.65-3.50 (1H, m), 3.32 (2H, q, J
= 7.0), 2.48-1.80 (8H, m), 2.16 (6H, s), 1.15 (3H,
t, J = 7.0). Physical properties: amorphous.

[0843]

Working Example 561 Cyclopropanecarboxylic acid = 8-ethoxymethoxy-3- (2,6-dimethylphenyl) -1-methoxymethoxy-1-azaspiro [4,5] decane-3-en-2-one -4-yl = ester (Compound No. 11-55) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.15-7.00 (3H, m), 5.06 (2
H, s), 4.77 (2H, s), 3.75-3.60 (1H, m), 3.64 (2H,
q, J = 7.0), 3.61 (3H, s), 2.19 (6H, s), 2.30-1.54
(8H, m), 1.24 (3H, t, J = 7.0), 0.89-0.73 (4H, m). Physical properties: oil.

[0844]

Working Example 562 8,8-Ethylenedioxy-4-hydroxy-3- (2,6-dimethylphenyl) -1-methoxymethoxy-1-azaspiro [4,5] decane-3-
En-2-one (Compound No. 11-56) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.43 (1H, brd. S), 7.20-7.0
1 (3H, m), 5.03 (2H, s), 3.89 (2H, t, J = 6.2), 3.61
(3H, s), 3.50 (2H, t, J = 6.2), 2.60-1.70 (8H, m),
2.19 (6H, s). Physical properties: crystals (melting point: 188-189 ° C).

[0845]

Working Example 563 Cyclopropanecarboxylic acid = 8,8-ethylenedioxy-3- (2,6-dimethylphenyl) -1-methoxymethoxy-1-azaspiro [4,5] decane-3-ene- 2-one-4-yl =
Ester (Compound No. 11-57) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.16-6.99 (3H, m), 5.08 (2
H, s), 4.00 (4H, s), 3.64 (3H, s), 2.55-2.49 (2H,
m), 2.19 (6H, s), 2.02-1.89 (6H, m), 0.85-0.72 (4
H, m). Physical properties: crystals (melting point: 140-142 ° C).

[0846]

Working Example 564 2-Methylpropionic Acid =
8,8-Ethylenedioxy-3- (2,6-dimethylphenyl) -1-methoxymethoxy-1-azaspiro [4,5] decane-3-en-2-one-4-yl ester (compound number 11-58) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.14-6.98 (3H, m), 5.08 (2
H, s), 3.98 (4H, s), 3.64 (3H, s), 2.58-2.39 (3H,
m), 2.20 (6H, s), 1.96-1.91 (6H, m), 0.95 (6H, d,
J = 7.0). Physical properties: crystals (melting point: 135-137 ° C).

[0847]

Working Example 565 2,2-Dimethylpropionic Acid = 8,8-ethylenedioxy-3- (2,6-dimethylphenyl) -1-methoxymethoxy-1-azaspiro [4,5] decane-3 -En-2-one-4-yl =
Ester (Compound No. 11-59) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.14-6.97 (3H, m), 5.08 (2
H, s), 3.98 (4H, s), 3.64 (3H, s), 2.58-2.41 (2H,
m), 2.20 (6H, s), 1.94-1.89 (6H, m), 1.01 (9H,
s). Physical properties: crystals (melting point: 181-282 ° C).

[0848]

Working Example 566 Ethyl carbonate = ester = 8,8-ethylenedioxy-3- (2,6-dimethylphenyl)-
1-methoxymethoxy-1-azaspiro [4,5] decane-3-en-2-one-4-yl ester (Compound No. 11-60) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.13- 7.00 (3H, m), 5.08 (2
H, s), 3.99 (4H, s), 3.94 (2H, q, J = 7.0), 3.64 (3
H, s), 2.56-2.40 (2H, m), 2.20 (6H, s), 2.04-1.92
(6H, m), 1.01 (3H, t, J = 7.0). Physical properties: crystals (melting point: 82-83 ° C).

[0849]

Working Example 567 Cyclopropanecarboxylic acid = 3- (2,6-dimethylphenyl) -1-methoxymethoxy-8,8-propylenedioxy-1-azaspiro [4,5] decane-3-ene- 2-On-4-yl ester (Compound No. 11-61) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.15-7.00 (3H, m), 5.07 (2
H, s), 3.99-3.91 (4H, m), 3.61 (3H, s), 2.50-1.51
(11H, m), 2.19 (6H, s), 0.84-0.71 (4H, m). Physical properties: crystals (melting point: 125-127 ° C).

[0850]

Working Example 568 Cyclopropanecarboxylic Acid = 1-ethoxymethoxy-3- (2,6-dimethylphenyl) -8-methoxymethoxy-1-azaspiro [4,5] decane-3-en-2-one -4-yl = ester (Compound No. 11-62) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.16-7.00 (3H, m), 5.12 (2H
, s), 4.73 (2H, s), 3.87 (2H, q, J = 7.0), 3.80-3.60
(1H, m), 3.40 (3H, s), 2.20 (6H, s), 2.30-1.56
(9H, m), 1.28 (3H, t, J = 7.0), 0.87-0.74 (4H, m). Physical properties: Crystal (melting point: 56-59 ° C).

[0851]

Working Example 569 Cyclopropane carboxylic acid = 1,8-bis (ethoxymethoxy) -3- (2,5
6-Dimethylphenyl) -1-azaspiro [4,5] decane-3-en-2-one-4-yl ester (Compound No. 11-63) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.16 -7.00 (3H, m), 5.12 (2
H, s), 4.77 (2H, s), 3.87 (2H, q, J = 7.0), 3.64 (2
(H, q, J = 7.0), 3.80-3.60 (1H, m), 2.19 (6H, s), 2.30
-1.56 (8H, m), 1.28 (3H, t, J = 7.0), 1.24 (3H, t, J
= 7.0), 0.86-0.77 (4H, m). Physical properties: oil.

[0852]

Example 570 Cyclopropanecarboxylic acid = 1-ethoxymethoxy-3- (2,6-dimethylphenyl) -8- (N-methoxyimino) -1-azaspiro [4,5] decane-3-ene -2-one-4-yl ester (Compound No. 11-64) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.17-7.00 (3H, m), 5.14 (2
H, s), 3.87 (3H, s), 3.84 (2H, q, J = 7.0), 3.20-3.0
0 (1H, m), 2.74-2.00 (8H, m), 2.19 (6H, s), 1.26
(3H, t, J = 7.0), 0.85-0.72 (4H, m). Physical properties: oil.

[0853]

Working Example 571 8,8-Ethylenedioxy-1-ethoxymethoxy-3- (2,6-dimethylphenyl) -4
-Hydroxy-1-azaspiro [4,5] decane-3-
En-2-one (Compound No. 11-65) ¹ H-NMR (CDCl ₃ ) δ (ppm): 11.59 (1H, s), 7.18-6.98 (3
H, m), 4.95 (2H, s), 3.90 (4H, s), 3.77 (2H, q, J =
7.1), 2.40-1.70 (8H, m), 2.08 (6H, s), 1.18 (3H, t,
J = 7.1). Physical properties: crystals (melting point: 161-163 ° C).

[0854]

Example 572 Propionic acid = 8,8-ethylenedioxy-1-ethoxymethoxy-3- (2,6
-Dimethylphenyl) -1-azaspiro [4,5] decane-3-en-2-one-4-yl ester (Compound No. 11-66) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.15- 6.99 (3H, m), 5.13 (2
H, s), 3.99 (4H, s), 3.89 (2H, q, J = 7.0), 2.57-2.3
7 (2H, m), 2.28 (2H, q, J = 7.0), 2.20 (6H, s), 1.96
1.85 (6H, m), 1.30 (3H, t, J = 7.0), 0.93 (3H, t, J =
7.0). Physical properties: oil.

[0855]

Working Example 573 2-Methylpropionic Acid =
8,8-ethylenedioxy-1-ethoxymethoxy-3
-(2,6-Dimethylphenyl) -1-azaspiro [4,5] decane-3-en-2-one-4-yl ester (Compound No. 11-67) ¹ H-NMR (CDCl ₃ ) δ ( ppm): 7.14-6.99 (3H, m), 5.13 (2
H, s), 3.98 (4H, s), 3.90 (2H, q, J = 7.0), 2.60-2.4
0 (3H, m), 2.20 (6H, s), 1.96-1.91 (6H, m), 1.30
(3H, t, J = 7.0), 0.95 (6H, d, J = 7.0). Physical properties: crystals (melting point: 136-141 ° C).

[0856]

Example 574 Cyclopropanecarboxylic acid = 8,8-ethylenedioxy-1-ethoxymethoxy-3- (2,6-dimethylphenyl) -1-azaspiro [4,5] decane-3-ene-2 -On-4-yl =
Ester (Compound No. 11-68) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.16-7.00 (3H, m), 5.13 (2
H, s), 4.00 (4H, s), 3.89 (2H, q, J = 7.3), 2.55-1.8
5 (9H, m), 2.19 (6H, s), 1.30 (3H, t, J = 7.3), 0.85-
0.74 (4H, m). Physical properties: crystals (melting point: 114-116 ° C).

[0857]

Example 575 2,2-Dimethylpropionic acid = 8,8-ethylenedioxy-1-ethoxymethoxy-3- (2,6-dimethylphenyl) -1-azaspiro [4,5] decane-3 -En-2-one-4-yl =
Ester (Compound No. 11-69) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.14-6.97 (3H, m), 5.13 (2
H, s), 3.97 (4H, s), 3.90 (2H, q, J = 7.0), 2.61-2.4
3 (2H, m), 1.96-1.85 (6H, m), 1.30 (3H, t, J = 7.0),
1.01 (9H, s). Physical properties: Crystal (melting point: 168-173 ° C).

[0858]

Working Example 576 Ethyl carbonate = ester = 8,8-ethylenedioxy-3- (2,6-dimethylphenyl)-
1-ethoxymethoxy-1-azaspiro [4,5] decane-3-en-2-one-4-yl ester (Compound No. 11-70) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.16- 7.00 (3H, m), 5.13 (2
H, s), 3.99 (4H, s), 3.94 (2H, t, J = 7.0), 3.90 (2
(H, t, J = 7.0), 2.60-2.51 (2H, m), 2.20 (6H, s), 2.01
-1.92 (6H, m), 1.30 (3H, t, J = 7.0), 1.01 (3H, t, J
= 7.0). Physical properties: oil.

[0859]

Example 577 8,8-Ethylenedioxy-3-
(2,6-dimethylphenyl) -4-hydroxy-1-
Methoxyethoxy-1-azaspiro [4,5] decane-
3-en-2-one (Compound No. 11-71) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.14-7.06 (3H, m), 4.26-4.1
0 (2H, m), 3.98-3.88 (2H, m), 3.72-3.67 (2H, m),
3.60-3.40 (1H, m), 3.42 (3H, s), 2.45-1.80 (9H,
m), 2.18 (6H, s). Physical properties: amorphous.

[0860]

Example 578 Cyclopropanecarboxylic acid = 8,8-ethylenedioxy-3- (2,6-dimethylphenyl) -1-methoxyethoxy-1-azaspiro [4,5] decane-3-ene-2 -On-4-yl =
Ester (Compound No. 11-74) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.15-7.00 (3H, m), 4.36 (2
H, t, J = 4.4), 4.01 (4H, s), 3.72 (2H, t, J = 4.4), 3.
44 (3H, s), 2.30-1.55 (9H, m), 0.85-0.73 (4H, m). Physical properties: Crystal (melting point: 77-79 ° C).

[0861]

Example 579 2-methoxybenzoic acid =
8,8-Ethylenedioxy-3- (2,6-dimethylphenyl) -1-methoxy-1-azaspiro [4,5] decane-3-en-2-one-4-yl ester (Compound No. 11) −77) ¹ H-NMR (CDCl ₃ ) δ (ppm): 8.23-8.18 (2H, m), 7.15-6.8
6 (5H, m), 4.06 (3H, s), 4.02-3.90 (4H, m), 3.84
(3H, s), 2.38-1.98 (8H, m), 2.25 (6H, s). Physical properties: oil.

[0862]

Working Example 580 1,8-Bis (ethoxymethoxy)-
3- (2,6-dimethylphenyl) -4-hydroxy-
1-Azaspiro [4,5] decane-3-en-2-one (Compound No. 11-78) ¹ H-NMR (CDCl ₃ ) δ (ppm): 7.83 (1H, brd.s), 7.20-7.06
(3H, m), 5.09, 5.06 (2H, s, s), 4.17-4.06 (2H,
m), 3.83 (2H, q, J = 7.0), 3.70-3.50 (1H, m), 3.37
(2H, q, J = 7.0), 2.49-1.80 (8H, m), 2.17 (6H, s),
1.27 (3H, t, J = 7.0), 1.16 (3H, t, J = 7.0). Physical properties: gum-like.

[0863]

Working Example 581 Cyclopropanecarboxylic acid = 8,8-ethylenedioxy-3- (2,6-dimethylphenyl) -1-hydroxy-1-azaspiro [4,5] decane-3-en-2- On-4-yl ester (Compound No. 11-79) ¹ H-NMR (CDCl ₃ ) δ (ppm): 10.66 (1H, brd.s), 7.15-6.9
9 (3H, m), 3.95 (4H, s), 2.35-1.51 (8H, m), 2.04
(6H, s), 0.88-0.68 (4H, m). Physical properties: Crystal (melting point: 180-182 ° C).

[0864] In the following preparation examples, the types and mixing ratios of the compound and the auxiliary agent are not limited to these, and can be changed in a wide range. Also, in the following description,% indicates mass percentage.

[0865]

Formulation Example 1 Emulsion Xylene 42.5% to compound 5% of compound No. 1-5
And 42.5% of dimethyl sulfoxide were added and dissolved, and then a mixture of polyoxyethylene castor oil ether and calcium alkylbenzene sulfonate (8: 2)
10% was mixed to form an emulsion. The drug is diluted with water and used as a spray liquid.

[0866]

Formulation Example 2 Wettable powder 79% of kaolin and 10% of diatomaceous earth are mixed with 5% of compound No. 1-5, and further 3% of sodium lauryl sulfate
And 3% of sodium ligninsulfonate were mixed and pulverized to obtain a wettable powder. This drug is diluted with water and used as a spray liquid.

[0867]

Formulation Example 3 Dust A 99% mixture (1: 1) of talc and calcium carbonate was added to 1% of the compound of Compound No. 1-5, mixed, and pulverized to obtain a dust. Spray this drug as it is.

[0868]

Formulation Example 4 Granules Compound No. 1-5 (2%) is bentonite fine powder 3
0%, talc 66%, sodium lignin sulfonate 2
%, Add water and knead until uniform.
Next, the mixture was granulated through a granulator and passed through a granulator, a dryer, and a sieve to obtain granules having a particle size of 0.6 to 1.0 mm. Spray this agent as it is on the soil surface.

[0869]

Formulation Example 5 Oil Agent 0.1% of the compound of Compound No. 1-5 is dissolved in white kerosene.
The whole was made 100% to obtain an oil agent.

[0870]

Test Example 1 Insecticidal Test of Plutella 5% Emulsion of the compound of the present invention was prepared according to Formulation Example 1, and diluted with water so that the active ingredient content was 200 ppm. 2)
It was added so as to be diluted 1000 times. ｝. Cabbage leaves were immersed in this chemical solution for 20 seconds, air-dried, and then placed in a 250 ml plastic cup. 10 larvae of the third instar larva were released to this and placed in a constant temperature room at 25 ° C., 16 hours: light, 8 hours: dark. Five days after the treatment, the number of dead insects was examined, and the mortality was calculated.

As a result, Compound Nos. 1-13 and 1-1
9, 1-22, 1-24, 1-26, 1-27, 1-2
8, 1-33, 1-35, 1-38, 1-39, 1-4
0, 1-41, 1-42, 1-49, 1-51, 1-5
4, 1-57, 1-59, 1-71, 1-74, 1-7
5, 1-76, 1-78, 1-83, 1-84, 1-8
6, 1-87, 1-88, 1-90, 1-99, 1-1
05, 1-111, 1-112, 1-123, 1-12
8, 1-130, 1-136, 1-137, 1-13
8, 1-139, 1-140, 1-143, 1-14
4, 1-146, 1-147, 1-148, 1-15
2, 1-154, 1-158, 1-167, 1-16
8, 1-169, 1-192, 2-3, 2-5, 2-
6, 2-8, 2-9, 2-11, 2-12, 2-18,
2-19, 2-20, 2-22, 2-23, 2-24,
2-25, 2-26, 5-16, 5-39, 5-67,
5-68, 5-70, 5-79, 5-99, 5-10
1, 5-104, 5-105, 5-106, 5-10
8, 5-109, 5-112, 6-4, 6-12, 6
The compounds of 16, 6-20 and 6-30 have a mortality of 100
%showed that.

[0873]

[Test Example 2] Insecticidal test of brown planthopper, A 5% emulsion of the compound of the present invention was prepared according to Formulation Example 1, and diluted with water so that the active ingredient became 10 ppm. 200)
It was added so as to be 0-fold diluted. ｝. Rice seedlings were placed in a cylinder, the roots were immersed in a drug solution, and ten third-stage larvae of the brown planthopper were released. At this time, the test insects and the drug solution were prevented from directly touching with the sponge. It was left under a condition of 25 ° C, 16 hours: light, 8 hours: dark with a lid. Five days later, the state of the insects was observed, and the mortality was determined.

As a result, Compound Nos. 1-5, 1-6 and 1
-13, 1-17, 1-19, 1-22, 1-24, 1
-26, 1-27, 1-28, 1-33, 1-35, 1
-38, 1-39, 1-40, 1-41, 1-42, 1
-49, 1-51, 1-53, 1-54, 1-57, 1
-71, 1-72, 1-74, 1-75, 1-76, 1
-78, 1-79, 1-83, 1-84, 1-86, 1
-87, 1-88, 1-90, 1-91, 1-95, 1
-99, 1-105, 1-106, 1-111, 1-1
12, 1-123, 1-128, 1-130, 1-13
4, 1-137, 1-139, 1-143, 1-14
4, 1-146, 1-147, 1-148, 1-15
4, 1-169, 1-275, 2-2, 2-3, 2-
5, 2-8, 2-9, 2-24, 2-25, 2-26,
2-34, 2-66, 2-114, 2-178, 2-1
94, 2-371, 5-1, 5-16, 5-39, 5-
67, 5-68, 5-70, 5-79, 5-93, 5-
99, 5-101, 5-104, 5-105, 5-10
6, 5-108, 5-109, 5-110, 5-16
4, 5-172, 5-176, 5-184, 6-12,
The compounds 6-30 and 7-22 exhibited a mortality of 85% or more.

[0874]

Test Example 3 Insecticidal Test of Leafhopper Leafhopper A 5% emulsion of the compound of the present invention was prepared according to Formulation Example 1, and diluted with water so that the active ingredient became 10 ppm. 200)
It was added so as to be 0-fold diluted. ｝. Rice seedlings were placed in a cylinder, the roots were immersed in a drug solution, and ten third-stage larvae of the leafhopper leafhopper were released. At this time, the test insects and the drug solution were prevented from directly touching with the sponge. Cover at 25 ° C, 16
Time: light, 8 hours: left under dark conditions. Five days later,
The state of the insects was observed and the mortality was determined.

As a result, Compound Nos. 1-5, 1-6, 1
-13, 1-17, 1-19, 1-22, 1-24, 1
-26, 1-27, 1-28, 1-33, 1-35, 1
-38, 1-39, 1-40, 1-41, 1-42, 1
-49, 1-51, 1-53, 1-54, 1-57, 1
-71, 1-72, 1-74, 1-75, 1-76, 1
-78, 1-79, 1-83, 1-84, 1-86, 1
-87, 1-88, 1-90, 1-91, 1-99, 1
-105, 1-106, 1-111, 1-112, 1-
123, 1-128, 1-130, 1-134, 1-1
37, 1-139, 1-143, 1-144, 1-14
6, 1-148, 1-154, 1-169, 2-2, 2
-3, 2-5, 2-8, 2-9, 2-24, 2-25,
2-26, 2-34, 2-66, 2-114, 2-17
8, 2-194, 2-371, 5-1, 5-16, 5-
39, 5-67, 5-68, 5-70, 5-79, 5-
93, 5-99, 5-101, 5-104, 5-10
5, 5-106, 5-108, 5-109, 5-11
0, 5-164, 5-172, 5-176, 6-12,
The compounds 6-30 and 7-22 exhibited a mortality of 85% or more.

[0876]

Test Example 4 Cotton Aphid Insecticidal Test A cucumber leaf leaf disk (4.5 cm × 4.5 cm) was placed on absorbent cotton moistened with water, and adult cotton aphids were released. After larvae were bred for 18 hours, the adults were removed and the number of larvae was adjusted to 10 per leaf disk.
A 5% emulsion of the compound of the present invention was prepared according to Formulation Example 1, and diluted with water so that the active ingredient became 200 ppm.
It was added so as to be 0-fold diluted. ｝, 2 ml of this chemical was sprayed on the leaf disk using a rotary spray tower. After air drying, place the leaf disk in a sealed container,
6 hours: light, 8 hours: placed in dark room. Five days after the treatment, the number of dead insects was investigated, and the mortality was calculated.

As a result, Compound Nos. 1-13 and 1-1
9, 1-22, 1-24, 1-26, 1-33, 1-3
5, 1-38, 1-39, 1-40, 1-41, 1-4
2, 1-49, 1-51, 1-54, 1-71, 1-7
4, 1-75, 1-76, 1-78, 1-83, 1-8
4, 1-86, 1-87, 1-88, 1-90, 1-9
1, 1-92, 1-99, 1-105, 1-111, 1
-112, 1-123, 1-128, 1-130, 1-
136, 1-137, 1-138, 1-139, 1-1
40, 1-143, 1-144, 1-146, 1-14
7, 1-148, 1-151, 1-152, 1-15
4, 1-155, 1-156, 1-158, 1-15
9, 1-160, 1-166, 1-167, 1-16
8, 1-169, 1-171, 1-192, 2-3, 2
-5, 2-6, 2-8, 2-9, 2-11, 2-12,
2-19, 2-20, 2-22, 2-23, 2-24,
2-25, 2-26, 2-34, 2-66, 2-17
8, 2-194, 2-371, 5-16, 5-39, 5
-67, 5-68, 5-70, 5-79, 5-93,5
-99, 5-101, 5-104, 5-105, 5-1
Compounds 08, 5-109, 5-188, 6-12, 6-16 and 6-30 showed 100% mortality.

[0878]

Test Example 5 Cotton Aphid Insecticidal Test A cucumber leaf leaf disk (4.5 cm × 4.5 cm) was placed on absorbent cotton moistened with water, and adult cotton aphids were released. After larvae were bred for 18 hours, the adults were removed and the number of larvae was adjusted to 10 per leaf disk.
A 5% emulsion of the compound of the present invention was prepared according to Formulation Example 1, and diluted with water so that the active ingredient content became 12.5 ppm.
It was added so as to be a 00-fold dilution. ｝, 2ml of this drug solution
Was sprayed on the leaf disk using a rotary spray tower.
After air drying, put the leaf disk in a sealed container,
16 hours: light, 8 hours: placed in a dark room. Five days after the treatment, the number of dead insects was investigated, and the mortality was calculated.

As a comparison, see Japanese Patent Application Laid-Open No. 4-22695.
Example No. 7 of Japanese Patent Publication No. 7 (Comparative Compound a) and Example No. 33 (Comparative Compound b) was used. Comparative compound a: 4-hydroxy-5,5-dimethyl-2
-Oxo-3- (2,4,6-trimethylphenyl)-
1,5-dihydropyrrole Comparative compound b: 4-hydroxy-5,5-dimethyl-2
-Oxo-3- (2,4-dichlorophenyl) -1,5
-Dihydropyrrole As a result, the mortality of Comparative Compounds a and b was 0, but the mortality of Compounds Nos. 1-99 and 2-8 of the present invention was 90%.

[0880]

Test Example 6 Insecticidal test of Aspergillus niger For comparison, Example N of JP-A-4-226957 was used.
o. The following test was performed on Compound 7 (Comparative Compound a).

A 5% emulsion of the compound of the present invention was prepared according to Formulation Example 1, and diluted with water so that the active ingredient content was 12.5 ppm.新 As a spreading agent, Shin-Gramin (registered trademark, manufactured by Sankyo Co., Ltd.) was added so as to be diluted 2000 times. ｝. Cabbage leaves were immersed in this chemical solution for 20 seconds, air-dried, and then placed in a 250 ml plastic cup.
10 larvae of the 3rd instar larva were released to this, and 25 ° C, 16
Time: light, 8 hours: placed in a dark thermostat. Five days after the treatment, the number of dead insects was examined, and the mortality was calculated.

As a comparison, comparative compound a described in Test Example 5 was used.

As a result, the mortality of Comparative Compound a was 0, but the mortality of Compound No. 1-99 of the present invention was 100%.

[0884]

[Test Example 7] Test for killing spider mites: Four adult spider mites were released on a leaf disk of cowpea, and the next day, the adults were removed. One week later, a 5% emulsion of the compound of the present invention was prepared according to Formulation Example 1, diluted with water so that the active ingredient became 200 ppm, and 新 as a spreading agent was added 2000 g of new gramin (registered trademark, manufactured by Sankyo Co., Ltd.). It was added so as to be double dilution. ｝, 2 ml of this chemical was sprayed on the leaf disk using a rotary spray tower. After air-drying, it was left under the conditions of 25 ° C., 16 hours: light, 8 hours: dark. Five days later, the number of surviving mites was investigated, and five or less compounds were considered effective (when the compound of the present invention was not sprayed, the number of mites at the time of the investigation was significantly increased).

As a result, Compound Nos. 1-13 and 1-1
7, 1-19, 1-27, 1-28, 1-33, 1-3
5, 1-38, 1-39, 1-40, 1-41, 1-4
2, 1-49, 1-51, 1-53, 1-54, 1-7
1, 1-72, 1-75, 1-79, 1-83, 1-8
4, 1-87, 1-99, 1-105, 1-106, 1
-111, 1-112, 1-123, 1-128, 1-
130, 1-134, 1-136, 1-137, 1-1
39, 1-143, 1-144, 1-146, 1-14
8, 1-169, 1-275, 2-3, 2-6, 2-
9, 2-19, 2-20, 2-22, 2-23, 2-2
5, 2-34, 2-66, 2-178, 5-1 and 5-1
6, 5-39, 5-67, 5-70, 5-79, 5-9
3, 5-99, 5-101, 5-104, 5-105,
5-106, 5-108, 5-109, 5-110, 5
-111, 5-112, 5-164, 6-4, 6-1
The compounds 2,6-16, 6-20 and 6-30 were determined to be effective.

[0886]

Test Example 8 Paddy field weed pre-emergence treatment A 100 cm ² pot was filled with paddy field soil, and the seeds of a sleepy and awakened foxtail were mixed with 1 cm of the surface layer. In addition, seedlings of paddy rice at the 2 leaf stage were transplanted into a flooded state and grown in a greenhouse. Three days later, a wettable powder prepared according to Formulation Example 1 was used to treat a flooded soil at a dose of 20 g / a, and 21 days later, the degree of growth inhibition was investigated.

As a result, Compound Nos. 1-6, 1-13,
1-17, 1-28, 1-42, 1-71, 1-75,
1-79, 1-83, 1-84, 1-86, 1-87,
1-99, 1-106, 1-111, 1-112, 1-
130, 1-143, 1-144, 1-146, 1-1
55, 2-11, 2-178, 5-1, 5-16, 5-
67, 5-68, 5-70, 5-79, 5-99, 5-
101, 5-104, 5-105, 5-106, 5-1
08, 5-109, 5-110, 6-10, 6-12,
Compounds 6-16, 6-20 and 7-22 exhibited a growth inhibition rate of 100%.

[0888]

The N-substituted dihydropyrrole derivatives of the present invention include, for example, Hemiptera, Lepidoptera, Coleoptera,
It shows an excellent control effect against a wide range of pests such as dipteran pests, hymenoptera pests, orthoptera pests, termite pests, thrips pests, spider mites and plant parasitic nematodes.

[0889] The N-substituted dihydropyrrole derivative of the present invention has excellent herbicidal activity.

──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. ⁷ Identification symbol FI theme coat ゛ (Reference) C07D 213/65 C07D 213/65 307/12 307/12 309/14 309/14 317/54 317/54 401 / 12 401/12 403/12 403/12 405/12 405/12 409/12 409/12 417/12 417/12 471/10 101 471/10 101 491/107 491/107 491/113 491/113 ( 72) Inventor Mitsuru Ito 1041 Yasu-cho, Yasu-cho, Yasu-gun, Shiga Pref. 1041 Yasu Sankyo Stock Company In-house (72) Inventor Toshiaki Iwasaki 2-336 Kitabukuro-cho, Omiya-shi, Saitama (72) Inventor Seichiro Kodama 6-8-22-401 Kamiochiai, Yono-shi, Saitama 5-1857-6, Mitsuhashi, Omiya City, Prefecture

Claims (22)

[Claims] (1) The following general formula:[Wherein, R¹Is a hydrogen atom, C₁~ C₆Alkyl group <
An alkyl group has one C_Three~ C₇Cycloalkyl group, 1
(The phenyl group is a halogen atom and a C
₁~ C₆1 to 5 members selected from the group consisting of alkyl groups
It may be substituted by a substituent. ) One or two C₁~
C₆An alkoxy group (the alkoxy group may have 1 to 5
It may be substituted by a halogen atom. ) One C_Two~
C₆An alkenyloxy group, one (C₁~ C₆Alkoki
C) C₁~ C₆An alkoxy group, one benzyloxy group,
One C₁~ C₆Alkylthio group, 1 to 3 halogens
Atom, one cyano group, one di (C₁~ C₆Alkyl)
An amino group or one 5- or 6-membered heterocyclic group
The ring group has 1 to 4 oxygen, sulfur or nitrogen atoms
Containing a halogen atom and C₁~ C₆Alkyl group
Alkyl groups are substituted by one to three halogen atoms.
May be. 1) or 2 substitutions selected from the group consisting of
May be substituted by a group. Be replaced by｝
No. 》, C_Three~ C₇Cycloalkyl group, C_Two~ C₆Alkene
(The alkenyl group is one to three halogen atoms)
May be replaced by ), C_Two~ C₆Alkynyl group,
Phenyl group (the phenyl group is a halogen atom and a C₁~
C₆1 to 5 positions selected from the group consisting of alkyl groups
It may be substituted by a substituent. ) 5- or 6-membered heterocyclic ring
Group—the heterocyclic group has 1 to 4 oxygen atoms,
Or contains a nitrogen atom and contains one C₁~ C₆Alkyl group (this
The alkyl group is substituted by 1 to 3 halogen atoms
May be. ). ｝, C_Two~ C_Ten
Alkylcarbonyl group (the alkylcarbonyl group is
1 to 3 halogen atoms, 1 C₁~ C₆Alkoxy
Group or one phenoxy group. ),
A benzoyl group (the benzoyl group is a halogen atom and
C₁~ C₆1 to 5 selected from the group consisting of alkyl groups
May be substituted. ), C_Two~ C₈Alkoki
Carbonyl group, di (C₁~ C₆Alkyl) carbamoyl
Group, C₁~ C₆Alkylsulfonyl group or phenylsulfo
A phenyl group (the phenylsulfonyl group is a halogen atom and
And C₁~ C₆1 to 5 selected from the group consisting of alkyl groups
May be substituted. ), R^TwoAnd R^ThreeAre the same or different and are a hydrogen atom, C₁~ C₆
Alkyl group—the alkyl group has one C_Three~ C₇Cyclo
An alkyl group, one phenyl group (the phenyl group
Logen atom, C₁~ C₆Alkyl group and C₁~ C₆Alkoki
By 1 to 5 substituents selected from the group consisting of
It may be replaced. ) One or two C₁~ C₆Alkoxy
Group, one (C₁~ C₆Alkoxy) C₁~ C₆Alkoxy
Group, 1 to 13 halogen atoms or 1 5 or
6-membered heterocyclic group (the heterocyclic group is a group consisting of 1 to 4 oxygen atoms
Containing carbon, sulfur or nitrogen atoms. Replaced by
May be. ｝, C_Three~ C₇Cycloalkyl group, C_Two~ C₆A
A alkenyl group (the alkenyl group contains 1 to 3 halogen
May be substituted by a thiol atom. ), C_Two~ C₆Alkynyl
Group, phenyl group (the phenyl group is a halogen atom, C
₁~ C₆Alkyl group and C₁~ C₆Group consisting of alkoxy groups
Substituted with 1 to 5 substituents selected from
No. ) Or a 5- or 6-membered heterocyclic group.
Contains 1 to 4 oxygen, sulfur or nitrogen atoms
And a halogen atom and C₁~ C₆Alkyl group (the alkyl
May be substituted by 1 to 3 halogen atoms.
No. 1) or 2 substituents selected from the group consisting of
May be replaced. Represents｝, or R^TwoAnd R^ThreeIs
Together with the carbon atom to which they are attached, 4-7
Member, cycloalkane, cycloalkene or cyclo
Alkanediene ring—the ring is one to three C₁~ C₆A
Alkyl group, one C₁~ C₆An alkoxy group, one (C ₁
~ C₆Alkoxy) C₁~ C₆An alkoxy group, one di
(C₁~ C₆Alkyl) amino group, one C₁~ C_FourArchi
A dioxy group or one N- (C₁~ C₆Alkoxy)
May be substituted by an imino group, and at any position the ring is oxygen
Atom, sulfur atom or formula NR⁶A group represented by the formula:
⁶Is C₁~ C₆Represents an alkyl group. Interrupted by
May be. Represents｝, R^FourIs a hydrogen atom, C_Two~ C_TenAlkylcarbonyl group (this
The alkylcarbonyl group has 1 to 3 halogen atoms.
Child, one C_Two~ C₇Alkylcarbonyloxy group, 1
C₁~ C₆By an alkoxy group or one phenoxy group
It may be replaced. ), C_Four~ C₇Cycloalkylcarboni
Group—the cycloalkylcarbonyl group is C₁~ C₆A
1 selected from the group consisting of a alkyl group and a halogen atom
Up to four substituents, one or two C₁~ C₆An alkoxy group,
One or two cyano groups or one phenyl group (the
The nil group has one C₁~ C₆Substituted by an alkoxy group
May be. ). ｝, C_Three~ C₇Arche
Carbonyl group (the alkenylcarbonyl group is 1
And may be substituted by up to three halogen atoms. ), Ba
Benzoyl group—the benzoyl group is a halogen atom and C
₁~ C₆An alkyl group (the alkyl group may have 1 to 3
Substituted by a halogen atom or one phenoxy group.
No. 1) to 5 substituents selected from the group consisting of
Or three C₁~ C₆An alkoxy group, one C_Two~ C₇Al
A killed carbonyloxy group, one C_Two~ C₇Alkoxyka
Rubonyl group, one C₁~ C₆Alkylthio group, one C
₁~ C₆Alkylsulfinyl group, one C₁~ C₆Archi
Rusulfonyl group, 1 phenoxy group, 1 cyano group
Or it may be substituted by one nitro group. ｝, 4 to
6-membered heterocyclic carbonyl group ｛The heterocyclic carbonyl group is
Contains 1 to 4 oxygen, sulfur or nitrogen atoms
And one to three C₁~ C₆Alkyl group (the alkyl group
Is substituted by 1 to 3 halogen atoms.
No. ) 1 to 3 C ₁~ C₆An alkoxy group, one C
₁~ C₆An alkylthio group or one halogen atom
And may be condensed with a benzene ring. ｝, C_Two
~ C₈Alkoxycarbonyl group ｛the alkoxycarbo
Nyl group has 1 to 3 halogen atoms, 1 C₁~ C₆
An alkoxy group, one C₁~ C₆Alkylthio group, one
A phenyl group (the phenyl group is a halogen atom and a C₁
~ C₆1 to 5 members selected from the group consisting of alkyl groups
It may be substituted by a substituent. ) Or one 5 or
6-membered heterocyclic group (the heterocyclic group is a group consisting of 1 to 4 oxygen atoms
Containing a sulfur atom, a nitrogen atom, a halogen atom and
C₁~ C₆1 or 2 selected from the group consisting of alkyl groups
May be substituted. )
No. ｝, C_Four~ C₇Cycloalkoxycarbonyl group, C_Three
~ C₇Alkenyloxycarbonyl group, C_Three~ C₇Archi
Nyloxycarbonyl group, (C₁~ C₆Alkylthio) ka
Rubonyl group, (phenylthio) carbonyl group
Enylthio) carbonyl group is a halogen atom and C₁~
C₆1 to 5 positions selected from the group consisting of alkyl groups
It may be substituted by a substituent. ｝, (C₁~ C₆Alkoki
B) thiocarbonyl group, (phenoxy) thiocarbonyl
Group—the (phenoxy) thiocarbonyl group is a halogen
Atom and C₁~ C₆1 selected from the group consisting of alkyl groups
It may be substituted with up to 5 substituents. ｝, C_Two~ C₇
Alkyldithiocarbonyl group, phenyldithiocarboni
Group (the phenyldithiocarbonyl group is a halogen atom
Child and C₁~ C₆1 selected from the group consisting of alkyl groups
It may be substituted by up to 5 substituents. ), C₁~ C₆A
Alkyl group—the alkyl group is one phenyl group
The phenyl group is a halogen atom, C₁~ C₆Alkyl group
And C₁~ C₆1 to 1 selected from the group consisting of alkoxy groups
It may be substituted by 5 substituents. ), C₁~ C₆Al
Coxy group, (C₁~ C₆Alkoxy) C₁~ C₆Alkoxy
Group, C₁~ C₆Alkylthio group, cyano group, phenoxy group
(The phenoxy group is a halogen atom and C₁~ C₆Al
1 to 5 substituents selected from the group consisting of
May be replaced. ) Or C_Two~ C₇Alkoxycarboni
May be substituted by a benzyl group. ｝, C_Two~ C₆Alkenyl
Group, C_Two~ C₆Alkynyl group, di (C₁~ C₆Alkyl) mosquito
Rubamoyl group—two of the dialkylcarbamoyl
Alkyl groups together with the nitrogen atom to which they are attached
5- or 6-membered heterocyclic ring (the heterocyclic ring is one nitrogen atom
Contain one oxygen or nitrogen atom in addition to the
No. ) May be formed. ｝, J (C₁~ C₆Alkyl)
Ocarbamoyl group ｛in the dialkylthiocarbamoyl
The two alkyl groups are one with the nitrogen atom to which they are attached.
5- or 6-membered heterocyclic ring (one heterocyclic ring
Contains one oxygen or nitrogen atom in addition to the nitrogen atom
May be. ) May be formed. ｝, C₁~ C₆Alkylsul
Phonyl group, phenylsulfonyl group (
A nyl group is a halogen atom and C₁~ C₆From an alkyl group
Substituted with 1 to 5 substituents selected from the group
Good. ) Or di (C₁~ C₆Alkoxy) thiophosphoryl
A represents C₁~ C₆Alkyl group (the alkyl group is 1 to
It may be substituted by 13 halogen atoms. ),Halo
Gen atom, C₁~ C₆An alkoxy group (the alkoxy group
Is substituted by 1 to 5 halogen atoms.
No. ), C₁~ C₆Alkylthio group, C₁~ C₆Alkyls
Ruphonyl group, phenyl group (the phenyl group is halogen
Atom and C₁~ C₆1 selected from the group consisting of alkyl groups
It may be substituted with up to 5 substituents. ) 5 young
Is a 6-membered heterocyclic group (the heterocyclic group is a group consisting of 1 to 4 oxygen atoms
Containing a sulfur atom, a nitrogen atom, a halogen atom and
C₁~ C₆1 or 2 selected from the group consisting of alkyl groups
May be substituted. ), Cyano group, nitro
Group, amino group or phenoxy group (the phenoxy group is
Halogen atom and C₁~ C₆Select from the group consisting of alkyl groups
It may be substituted by 1 to 5 substituents. )
And n represents an integer of 1 to 5, X represents an oxygen atom, a sulfur atom, a sulfinyl group or a sulfo group.
Represents a nyl group. N-substituted dihydropyrrole represented by the formula:
Derivatives or salts thereof. (2) R¹Is a hydrogen atom, C₁~ C_FourAlkyl group
<< The alkyl group has one C_Three~ C₇Cycloalkyl
Group, one phenyl group (the phenyl group is a chlorine atom,
Fluorine atom, bromine atom and C₁~ C_FourConsists of an alkyl group
Substituted with 1 to 3 substituents selected from the group.
No. ) One or two C₁~ C_FourAlkoxy group (the
Coxy groups have 1 to 5 chlorine atoms, fluorine atoms or odors.
It may be substituted by an elementary atom. ) One C_Three~ C_FiveAl
Kenyloxy group, one (C₁~ C_FourAlkoxy) C ₁~
C_FourAn alkoxy group, one benzyloxy group, one C₁
~ C_FourAlkylthio group, 1 to 3 chlorine atoms, fluorine
Atom or bromine atom, one cyano group, one di (C
₁~ C_FourAlkyl) amino group or one 5- or 6-membered compound
A heterocyclic group ｛the heterocyclic group has 1 to 3 oxygen atoms,
Atom or nitrogen atom, chlorine atom, fluorine atom, odor
Elementary atom and C₁~ C_FourAlkyl group (the alkyl group is 1
From 3 to 3 chlorine, fluorine or bromine atoms
May be replaced. )) Or one or two selected from the group consisting of
It may be substituted by a substituent. Be replaced by｝
No. 》, C_Three~ C₇Cycloalkyl group, C_Three~ C_FiveAlkene
(The alkenyl group is one to three chlorine atoms,
It may be substituted by a nitrogen atom or a bromine atom. ), C _Three
~ C_FiveAlkynyl group, phenyl group (the phenyl group is
Chlorine atom, fluorine atom, bromine atom and C₁~ C_FourAlkyl
With one to three substituents selected from the group consisting of
May be replaced. ) 5- or 6-membered heterocyclic group
The ring group has 1 to 3 oxygen, sulfur or nitrogen atoms
Containing one C₁~ C_FourAlkyl group (the alkyl group
Represents 1 to 3 chlorine, fluorine or bromine atoms
More may be substituted. ). ｝, C
_Two~ C₈Alkylcarbonyl group (the alkylcarbonyl group
The group is one to three chlorine atoms, fluorine atoms or bromine
Atom, one C₁~ C_FourAlkoxy group or one phenoxy
It may be substituted by a group. ), Benzoyl group (
Benzoyl groups are chlorine, fluorine, bromine and C
₁~ C_Four1 to 3 members selected from the group consisting of alkyl groups
It may be substituted by a substituent. ), C_Two~ C_FiveAlkoxy
Carbonyl group, di (C₁~ C_FourAlkyl) carbamoyl
Group, C₁~ C_FourAlkylsulfonyl group or phenylsulfo
A phenyl group (the phenylsulfonyl group is a chlorine atom,
Elemental atom, bromine atom and C₁~ C_FourGroup consisting of alkyl groups
Substituted with one to three substituents selected from
No. The N-substituted dihydropyro according to claim 1, which is
Derivatives or salts thereof. (3) R¹Is a hydrogen atom, C₁~ C_ThreeAlkyl group
{The alkyl group has one C_Three~ C₆Cycloalkyl
Group, one phenyl group, one or two C₁~ C_ThreeAlkoki
Si group (the alkoxy group has 1 to 3 chlorine atoms or
It may be substituted by a fluorine atom. ), One (C₁~
C_ThreeAlkoxy) C₁~ C_ThreeAlkoxy group, one benzene
Roxy group, one C₁~ C_ThreeAlkylthio group, 1-3
Chlorine or fluorine atoms, one cyano group or
One 5- or 6-membered heterocyclic group (the heterocyclic group is
Contains two oxygen or nitrogen atoms. )
May be replaced. ｝, C _Three~ C₆Cycloalkyl group, C_Three~
C_FourAn alkenyl group (wherein the alkenyl group is one or two
It may be substituted by a chlorine atom or a fluorine atom. ), C
_Three~ C_FourAlkynyl group, phenyl group, 5- or 6-membered complex
A ring group (the heterocyclic group is one or two oxygen atoms or nitrogen
Contains atoms. ), C_Two~ C₆Alkylcarbonyl group,
Benzoyl group, C_Two~ C_FourAlkoxycarbonyl group, di
(C₁~ C_ThreeAlkyl) carbamoyl group, C₁~ C_ThreeArchi
A rusulfonyl group or a phenylsulfonyl group.
Item 7. The N-substituted dihydropyrrole derivative or the derivative thereof according to item 1.
salt. 4. R ¹ is a C ₁ -C ₂ alkyl group. The alkyl group has one C ₁ -C ₂ alkoxy group and one (C ₁ -C ₂
C ₂ alkoxy) C ₁ -C ₂ alkoxy group or one C ₁ ~
It may be substituted by a C ₂ alkylthio group. ｝
The N-substituted dihydropyrrole derivative according to claim 1 or a salt thereof. 5. The N- according to claim 1, wherein R ¹ is a C ₁ -C ₂ alkyl group (the alkyl group may be substituted by one C ₁ -C ₂ alkoxy group). A substituted dihydropyrrole derivative or a salt thereof. 6. R^TwoAnd R^ThreeAre the same or different and C₁~
C_FourAlkyl group—the alkyl group has one C_Three~ C₇Shi
Chloroalkyl group, one phenyl group (the phenyl group
Is a chlorine atom, a fluorine atom, a bromine atom, C₁~ C_FourArchi
And C₁~ C_FourSelected from the group consisting of alkoxy groups
It may be substituted by 1 to 3 substituents. ), 1 or
Two C₁~ C_FourAn alkoxy group, one (C₁~ C_FourArco
Kishi) C₁~ C_FourAn alkoxy group, 1 to 5 chlorine atoms,
Fluorine atom or bromine atom or one 5 or 6 member
A heterocyclic group (the heterocyclic group has 1 to 3 oxygen atoms,
Contains yellow or nitrogen atoms. )
No. ｝, C_Three~ C₇Cycloalkyl group, C_Three~ C_FiveAlkene
(The alkenyl group is one to three chlorine atoms,
It may be substituted by a nitrogen atom or a bromine atom. ), C_Three
~ C_FiveAlkynyl group, phenyl group (the phenyl group is
Chlorine atom, fluorine atom, bromine atom, C₁~ C_FourAlkyl group
And C ₁~ C_Four1 selected from the group consisting of alkoxy groups
It may be substituted by up to three substituents. ) Or 5 young
Is a 6-membered heterocyclic group. The heterocyclic group has 1 to 3 oxygen atoms.
Containing sulfur, nitrogen or nitrogen atom, chlorine atom, fluorine
Atom, bromine atom and C₁~ C_FourAlkyl group (the alkyl
The group is one to three chlorine, fluorine or bromine atoms
May be replaced by ) Or one selected from the group consisting of
May be substituted by two substituents. Represents｝, and
Is R^TwoAnd R^ThreeIs the same as the carbon atom to which they are attached.
In the meantime, 4- to 7-membered cycloalkane, cycloa
Alkene or cycloalkanediene ring—the ring is 1
Or three C₁~ C_FourAlkyl group, one C₁~ C_FourArco
Xyl group, one (C₁~ C_FourAlkoxy) C₁~ C_FourArco
A xyl group, one di (C₁~ C_FourAlkyl) amino group, 1
Methylenedioxy group, one ethylenedioxy group,
One trimethylenedioxy group or one N- (C₁~ C_Four
An alkoxy) imino group,
Where the ring is an oxygen atom, a sulfur atom or a formula NR^6aGroup represented by
(Where R^6aIs C₁~ C_FourRepresents an alkyl group. By)
May be interrupted. 6. Any of claims 1 to 5, wherein
The N-substituted dihydropyrrole derivative according to any one of the above, or
Its salt. 7. R ² and R ³ are the same or different and each has a C ₁ to
C ₃ alkyl group ｛The alkyl group is one C ₃ -C ₆ cycloalkyl group and one phenyl group (the phenyl group is a chlorine atom, a fluorine atom, a C ₁ -C ₃ alkyl group and
It may be substituted by one or two substituents selected from the group consisting of ₁ to ₃ alkoxy groups. ) One or two C ₁
-C ₃ alkoxy groups, the one (C ₁ -C ₃ alkoxy) C ₁
-C ₃ alkoxy groups, 1 to 3 chlorine atoms or fluorine atoms or one 5- or 6-membered Hajime Tamaki (said heterocyclic group containing one or two oxygen atoms or nitrogen atoms.) By It may be replaced. }, C ₃ -C ₆ cycloalkyl group, C ₃ -C ₄ alkenyl group, C ₃ -C ₄ alkynyl group, a phenyl group (said phenyl group is 1 or 2 C ₁
~C may be substituted by ₃ alkoxy groups. ) Or a 5- or 6-membered heterocyclic group (the heterocyclic group contains one or two oxygen or nitrogen atoms), or R ²
And R ³ together with the carbon atom to which they are attached, are a 4- to 6-membered cycloalkane, cycloalkene or cycloalkanediene ring, wherein said ring is 1 or 2
C ₁ -C ₃ alkyl groups, one C ₁ -C ₃ alkoxy group, one (C ₁ -C ₃ alkoxy) C ₁ -C ₃ alkoxy group, one di (C ₁ -C ₃ Alkyl) amino group, one ethylenedioxy group, one trimethylenedioxy group or one N- (C ₁ -C ₃ alkoxy) imino group, wherein at any position the ring is oxygen It may be interrupted by an atom, a sulfur atom or a group represented by the formula NR ^6b , wherein R ^6b represents a C ₁ -C ₃ alkyl group. ｝
An N-substituted dihydropyrrole derivative or a salt thereof according to any one of claims 1 to 5. 8. R ² and R ³ are the same or different and each has a C ₁ to R
Represents a C ₂ alkyl group, or R ² and R ³ together with the carbon atom to which they are attached, a cyclohexane ring {the cyclohexane ring is one or two C ₁ -C ₂ alkyl groups; One C ₁ -C ₂ alkoxy group and one (C ₁
-C ₂ alkoxy) C ₁ -C ₂ alkoxy, one ethylenedioxy, one trimethylenedioxy or 1
N- (C ₁ -C ₂ alkoxy) imino groups. The N-substituted dihydropyrrole derivative or a salt thereof according to any one of claims 1 to 5, which is｝. 9. R ² and R ³ both represent a methyl group, or R ² and R ³ together with the carbon atom to which they are attached form a cyclohexane ring ｛the cyclohexane ring It may be substituted by one C ₁ -C ₂ alkoxy group, ethylenedioxy group, trimethylenedioxy group or N- (C ₁ -C ₂ alkoxy) imino group. The N-substituted dihydropyrrole derivative or a salt thereof according to any one of claims 1 to 5, which is｝. 10. A compound according to claim 1, wherein R ⁴ is a hydrogen atom, a C ₂ -C ₈ alkylcarbonyl group (the alkylcarbonyl group is one to three chlorine, fluorine or bromine, one C ₂
-C ₅ alkylcarbonyloxy group may be substituted by one C ₁ -C ₄ alkoxy groups or one phenoxy group. ), C ₄ -C ₇ cycloalkylcarbonyl group {wherein the cycloalkylcarbonyl group is ₁ to ₄ substituents selected from the group consisting of a C ₁ -C ₄ alkyl group, a chlorine atom, a fluorine atom and a bromine atom; Or two C ₁ -C ₄ alkoxy groups, one or two cyano groups or one phenyl group (the phenyl group may be substituted by one C ₁ -C ₄ alkoxy group). May be. ｝, C ₃ -C ₆
Alkenylcarbonyl group (the alkenylcarbonyl group may be substituted by 1 to 3 chlorine atoms, fluorine atoms or bromine atoms), benzoyl group {the benzoyl group includes chlorine atom, fluorine atom, bromine atom and C ₁ ~ C ₄
1 selected from the group consisting of an alkyl group (the alkyl group may be substituted by 1 to 3 chlorine atoms, fluorine atoms or bromine atoms, or one phenoxy group).
1 to 3 substituents, 1 to 3 C ₁ -C ₄ alkoxy groups, 1 C ₂ -C ₅ alkylcarbonyloxy group, 1 C ₂ -C ₅ alkoxycarbonyl group, 1 C ₁ -C ₄ alkylthio group, one C ₁ -C ₄ alkylsulfinyl group, one C ₁ -C ₄ alkylsulfonyl group, substituted by one phenoxy group, one cyano group or one nitro group May be. {4- to 6-membered heterocyclic carbonyl group} The heterocyclic carbonyl group contains 1 to 3 oxygen, sulfur or nitrogen atoms, and contains 1 or 2 C _{1 to} C ₄ alkyl groups (the alkyl The group may be substituted by one to three chlorine, fluorine or bromine atoms.) One or two C ₁ -C ₄ alkoxy groups, one C ₁ -C ₄ alkylthio group or one May be substituted by a chlorine atom, a fluorine atom or a bromine atom, and may be condensed with a benzene ring. {C ₂ -C ₈ alkoxycarbonyl group} The alkoxycarbonyl group has 1 to 3 chlorine atoms, fluorine atoms or bromine atoms, 1 C ₁ -C ₄ alkoxy group, 1
C ₁ -C ₄ alkylthio groups, one phenyl group (the phenyl group is a chlorine atom, a fluorine atom, a bromine atom,
It may be substituted by 1 to 3 substituents selected from the group consisting of ₁ to ₄ alkyl groups. ) Or one 5- or 6-membered heterocyclic group (the heterocyclic group contains 1 to 3 oxygen atoms, sulfur atoms or nitrogen atoms, chlorine atom, fluorine atom, bromine atom and C ₁ -C ₄ (It may be substituted by one or two substituents selected from the group consisting of alkyl groups.)
May be replaced by }, C ₅ ~C ₇ cycloalkoxycarbonyl group, C ₄ -C ₇ alkenyloxycarbonyl groups, C ₄ -C ₇ alkynyloxy group, (C ₁ ~
C ₄ alkylthio) carbonyl group, (phenylthio) carbonyl group ｛The (phenylthio) carbonyl group is one to three substituents selected from the group consisting of a chlorine atom, a fluorine atom, a bromine atom and a C ₁ -C ₄ alkyl group. May be replaced by ｝, (C ₁ -C ₄ alkoxy) thiocarbonyl group, (phenoxy) thiocarbonyl group ｛The (phenoxy) thiocarbonyl group is selected from the group consisting of a chlorine atom, a fluorine atom, a bromine atom and a C ₁ -C ₄ alkyl group. It may be substituted by one to three selected substituents. ｝, C ₂ ~
C ₆ alkyldithiocarbonyl group, phenyldithiocarbonyl group (the phenyldithiocarbonyl group is substituted by 1 to 3 substituents selected from the group consisting of a chlorine atom, a fluorine atom, a bromine atom and a C ₁ -C ₄ alkyl group) A C ₁ -C ₄ alkyl group {the alkyl group is
One phenyl group (the phenyl group is a chlorine atom, a fluorine atom, a bromine atom, a C ₁ -C ₄ alkyl group and a C ₁ -C ₄
It may be substituted by 1 to 3 substituents selected from the group consisting of alkoxy groups. ), C ₁ -C ₄ alkoxy groups,
(C ₁ -C ₄ alkoxy) C ₁ -C ₄ alkoxy, C ₁ -C ₄
A C ₄ alkylthio group, a cyano group, a phenoxy group (the phenoxy group is a chlorine atom, a fluorine atom, a bromine atom,
It may be substituted by 1 to 3 substituents selected from the group consisting of ₁ to ₄ alkyl groups. ) Or it may be substituted by C ₂ -C ₅ alkoxycarbonyl group. }, C ₃ -C ₅ alkenyl group, C ₃ -C ₅ alkynyl group, di two alkyl groups (C ₁ -C ₄ alkyl) carbamoyl group {in the dialkylcarbamoyl, together with the nitrogen atom to which they are attached To form a 5- or 6-membered heterocycle (the heterocycle may contain one oxygen atom or one nitrogen atom in addition to one nitrogen atom). {Di (C ₁ -C ₄ alkyl) thiocarbamoyl group} The two alkyl groups in the dialkylthiocarbamoyl together with the nitrogen atom to which they are attached are a 5- or 6-membered heterocycle (the heterocycle is May contain one oxygen atom or one nitrogen atom in addition to one nitrogen atom). ｝, A C ₁ -C ₄ alkylsulfonyl group, a phenylsulfonyl group (the phenylsulfonyl group is selected from the group consisting of a chlorine atom, a fluorine atom, a bromine atom and a C ₁ -C ₄ alkyl group;
May be substituted. ) Or di (C ₁ -C ₄₎
10. An alkoxy) thiophosphoryl group.
The N-substituted dihydropyrrole derivative or a salt thereof according to any one of the above. 11. R^FourIs a hydrogen atom, C_Two~ C₆Alkylka
Rubonyl group (1 to 3 alkylcarbonyl groups
Chlorine or fluorine atom, one C_Two~ C_FourArchi
Carbonyloxy group, one C₁~ C_ThreeAlkoxy group or
May be substituted by one phenoxy group. ), C_Four
~ C₇Cycloalkylcarbonyl group ｛the cycloalkyl
Carbonyl group is one to four C₁~ C_ThreeAlkyl group,
Chlorine atom or fluorine atom, one C₁~ C_ThreeAlkoki
Group, one cyano group or one phenyl group (the
The nil group has one C₁~ C_ThreeSubstituted by an alkoxy group
May be. ). ｝, C_Three~ C_FiveArche
Carbonyl group (the alkenylcarbonyl group is 1
Or two substituted by chlorine or fluorine atoms
No. ), Benzoyl group ｛The benzoyl group is a chlorine atom
Atom, fluorine atom and C₁~ C_ThreeAlkyl group (the alkyl
The group is 1 to 3 chlorine or fluorine atoms or 1
Phenoxy groups. Group consisting of)
1 or 2 substituents selected from 1 or 2 C₁~
C_ThreeAn alkoxy group, one C_Two~ C_FourAlkylcarbonyl
An oxy group, one C_Two~ C_FourAlkoxycarbonyl group, 1
C₁~ C_ThreeAlkylthio group, one C₁~ C_ThreeAlkyl
Sulfinyl group, one C₁~ C_ThreeAlkylsulfonyl
Group, one phenoxy group, one cyano group or one
It may be substituted by a toro group. ｝ 4- to 6-membered heterocyclic ring
Rubonyl group—the heterocyclic carbonyl group has 1 to 3
Containing 1 or 2 oxygen, sulfur or nitrogen atoms
C₁~ C_ThreeAlkyl group (1 to 3 alkyl groups
May be substituted by a chlorine atom or a fluorine atom. ),
One or two C₁~ C_ThreeAn alkoxy group, one C₁~ C_ThreeA
Alkylthio or one chlorine or fluorine atom
And may be condensed with a benzene ring.
No. ｝, C_Two~ C₈Alkoxycarbonyl group ｛the alcohol
An oxycarbonyl group is one to three chlorine atoms or
Nitrogen atom, one C₁~ C_ThreeAn alkoxy group, one C₁~
C_ThreeAn alkylthio group, one phenyl group or one
Or a 6-membered heterocyclic group (the heterocyclic group is one or two acids
Contains elemental or nitrogen atoms. )
No. ｝, C₆~ C₇Cycloalkoxycarbonyl group, C_Four
~ C₆Alkenyloxycarbonyl group, C_Four~ C₆Archi
Nyloxycarbonyl group, (C₁~ C_ThreeAlkylthio) ka
Rubonyl group, (phenylthio) carbonyl group, (C₁~
C_ThreeAlkoxy) thiocarbonyl group, (phenoxy) thio
Ocarbonyl group, C _Two~ C_FiveAlkyldithiocarbonyl
Group, phenyldithiocarbonyl group, C₁~ C_ThreeAlkyl group
{The alkyl group is one phenyl group, C₁~ C_ThreeA
Alkoxy group, (C₁~ C_ThreeAlkoxy) C₁~ C_ThreeAlkoki
Si group, C₁~ C_ThreeAlkylthio group, cyano group, phenoxy
Group or C_Two~ C_FourSubstituted by an alkoxycarbonyl group
May be. ｝, C_Three~ C_FourAlkenyl group, C_Three~ C_FourAlkini
Lu group, di (C₁~ C_ThreeAlkyl) carbamoyl group
The two alkyl groups in the alkylcarbamoyl are
Is a 5- or 6-membered complex together with the nitrogen atom to which
Ring (the heterocycle is one nitrogen atom and one oxygen atom
May contain atoms or nitrogen atoms. Form)
No. ｝, J (C₁~ C_ThreeAlkyl) thiocarbamoyl group
２Two alkyls in the dialkylthiocarbamoyl
The groups together with the nitrogen atom to which they are attached
Or a 6-membered heterocyclic ring (the heterocyclic ring is, in addition to one nitrogen atom,
It may contain one oxygen or nitrogen atom. Form)
May do it. ｝, C₁~ C_ThreeAlkylsulfonyl group, phenyl
Rusulfonyl group or di (C₁~ C_ThreeAlkoxy) thiophos
10. The compound according to claim 1, which is a folyl group.
An N-substituted dihydropyrrole derivative or a salt thereof. 12. R ⁴ is a hydrogen atom, a C ₂ -C ₄ alkylcarbonyl group or a cyclopropylcarbonyl group (the cyclopropylcarbonyl group may be substituted by one C ₁ -C ₂ alkyl group). , C ₃ -C ₄ alkenyl group, a benzoyl group or a C ₂ -C ₃ alkoxycarbonyl group, according to any one of claims 1 to 9 N-
A substituted dihydropyrrole derivative or a salt thereof. 13. R ⁴ is a hydrogen atom, a C ₂ -C ₄ alkylcarbonyl group, a cyclopropylcarbonyl group (the cyclopropylcarbonyl group may be substituted by one methyl group) or a C ₂ -C 4 group. The N-substituted dihydropyrrole derivative or a salt thereof according to any one of claims 1 to 9, which is a ₃ alkoxycarbonyl group. 14. A is a C ₁ -C ₄ alkyl group (the alkyl group may be substituted by 1 to 5 chlorine atoms, fluorine atoms or bromine atoms), a chlorine atom, a fluorine atom,
Bromine, C ₁ -C ₄ alkoxy group (said alkoxy group is 1 to 3 chlorine atoms may be substituted by a fluorine atom or a bromine atom.), C ₁ -C ₄ alkylthio groups, C
₁ -C ₄ alkylsulfonyl group, a phenyl group (said phenyl group, a chlorine atom, a fluorine atom, a bromine atom and C ₁ -C ₄
It may be substituted by 1 to 3 substituents selected from the group consisting of an alkyl group. ) A 5- or 6-membered heterocyclic group (the heterocyclic group contains 1 to 3 oxygen, sulfur or nitrogen atoms and is selected from chlorine, fluorine, bromine and C ₁ -C ₄ alkyl) May be substituted with one or two substituents selected from the group consisting of: a cyano group, a nitro group, an amino group and a phenoxy group (the phenoxy group is a chlorine atom, a fluorine atom, a bromine atom and C ₁ -C The N-substituted dihydropyrrole derivative or a salt thereof according to any one of claims 1 to 13, wherein the N-substituted dihydropyrrole derivative may be substituted with 1 to 3 substituents selected from the group consisting of ₄ alkyl groups. 15. A is a C ₁ -C ₃ alkyl group (the alkyl group may be substituted by 1 to 3 chlorine atoms or fluorine atoms), a chlorine atom, a fluorine atom, a bromine atom,
C ₁ -C ₃ alkoxy group, C ₁ -C ₃ alkylthio group, C ₁
-C ₃ alkylsulfonyl group, a phenyl group, 5- or 6-membered Hajime Tamaki (said heterocyclic group containing one or two oxygen atoms or nitrogen atoms.), A cyano group, a nitro group, an amino group or a phenoxy The N-substituted dihydropyrrole derivative or a salt thereof according to any one of claims 1 to 13, which is a group. 16. The N-substituted dihydropyrrole derivative or a salt thereof according to any one of claims 1 to 13, wherein A is a methyl group or a chlorine atom. 17. The method according to claim 1, wherein n is 2 or 3.
6. The N-substituted dihydropyrrole derivative or a salt thereof according to any one of 6. 18. The method according to claim 1, wherein X is an oxygen atom.
8. The N-substituted dihydropyrrole derivative or a salt thereof according to any one of 7. 19. The method according to claim 1, wherein X is a sulfur atom.
8. The N-substituted dihydropyrrole derivative or a salt thereof according to any one of 7. 20. The following general formula:[Wherein, R¹Is a hydrogen atom, C₁~ C₆Alkyl group <
An alkyl group has one C_Three~ C₇Cycloalkyl group, 1
(The phenyl group is a halogen atom and a C
₁~ C₆1 to 5 members selected from the group consisting of alkyl groups
It may be substituted by a substituent. ) One or two C₁~
C₆An alkoxy group (the alkoxy group may have 1 to 5
It may be substituted by a halogen atom. ) One C_Two~
C₆An alkenyloxy group, one (C₁~ C₆Alkoki
C) C₁~ C₆An alkoxy group, one benzyloxy group,
One C₁~ C₆Alkylthio group, 1 to 3 halogens
Atom, one cyano group, one di (C₁~ C₆Alkyl)
An amino group or one 5- or 6-membered heterocyclic group
The ring group has 1 to 4 oxygen, sulfur or nitrogen atoms
Containing a halogen atom and C₁~ C₆Alkyl group
Alkyl groups are substituted by one to three halogen atoms.
May be. 1) or 2 substitutions selected from the group consisting of
May be substituted by a group. Be replaced by｝
No. 》, C_Three~ C₇Cycloalkyl group, C_Two~ C₆Alkene
(The alkenyl group is one to three halogen atoms)
May be replaced by ), C_Two~ C₆Alkynyl group,
Phenyl group (the phenyl group is a halogen atom and a C₁~
C₆1 to 5 positions selected from the group consisting of alkyl groups
It may be substituted by a substituent. ) 5- or 6-membered heterocyclic ring
Group—the heterocyclic group has 1 to 4 oxygen atoms,
Or contains a nitrogen atom and contains one C₁~ C₆Alkyl group (this
The alkyl group is substituted by 1 to 3 halogen atoms
May be. ). ｝, C_Two~ C_Ten
Alkylcarbonyl group (the alkylcarbonyl group is
1 to 3 halogen atoms, 1 C₁~ C₆Alkoxy
Group or one phenoxy group. ),
A benzoyl group (the benzoyl group is a halogen atom and
C₁~ C₆1 to 5 selected from the group consisting of alkyl groups
May be substituted. ), C_Two~ C₈Alkoki
Carbonyl group, di (C₁~ C₆Alkyl) carbamoyl
Group, C₁~ C₆Alkylsulfonyl group or phenylsulfo
A phenyl group (the phenylsulfonyl group is a halogen atom and
And C₁~ C₆1 to 5 selected from the group consisting of alkyl groups
May be substituted. ), R^TwoAnd R^ThreeAre the same or different and are a hydrogen atom, C₁~ C₆
Alkyl group—the alkyl group has one C_Three~ C₇Cyclo
An alkyl group, one phenyl group (the phenyl group
Logen atom, C₁~ C₆Alkyl group and C₁~ C₆Alkoki
By 1 to 5 substituents selected from the group consisting of
It may be replaced. ) One or two C₁~ C₆Alkoxy
Group, one (C₁~ C₆Alkoxy) C₁~ C₆Alkoxy
Group, 1 to 13 halogen atoms or 1 5 or
6-membered heterocyclic group (the heterocyclic group is a group consisting of 1 to 4 oxygen atoms
Containing carbon, sulfur or nitrogen atoms. Replaced by
May be. ｝, C_Three~ C₇Cycloalkyl group, C_Two~ C₆A
A alkenyl group (the alkenyl group contains 1 to 3 halogen
May be substituted by a thiol atom. ), C_Two~ C₆Alkynyl
Group, phenyl group (the phenyl group is a halogen atom, C
₁~ C₆Alkyl group and C₁~ C₆Group consisting of alkoxy groups
Substituted with 1 to 5 substituents selected from
No. ) Or a 5- or 6-membered heterocyclic group.
Contains 1 to 4 oxygen, sulfur or nitrogen atoms
And a halogen atom and C₁~ C₆Alkyl group (the alkyl
May be substituted by 1 to 3 halogen atoms.
No. 1) or 2 substituents selected from the group consisting of
May be replaced. Represents｝, or R^TwoAnd R^ThreeIs
Together with the carbon atom to which they are attached, 4-7
Member, cycloalkane, cycloalkene or cyclo
Alkanediene ring—the ring is one to three C₁~ C₆A
Alkyl group, one C₁~ C₆An alkoxy group, one (C ₁
~ C₆Alkoxy) C₁~ C₆An alkoxy group, one di
(C₁~ C₆Alkyl) amino group, one C₁~ C_FourArchi
A dioxy group or one N- (C₁~ C₆Alkoxy)
May be substituted by an imino group, and at any position the ring is oxygen
Atom, sulfur atom or formula NR⁶A group represented by the formula:
⁶Is C₁~ C₆Represents an alkyl group. Interrupted by
May be. ｝, A is C₁~ C₆Alkyl group (the alkyl group is 1 to
It may be substituted by 13 halogen atoms. ),Halo
Gen atom, C₁~ C₆An alkoxy group (the alkoxy group
Is substituted by 1 to 5 halogen atoms.
No. ), C₁~ C₆Alkylthio group, C₁~ C₆Alkyls
Ruphonyl group, phenyl group (the phenyl group is halogen
Atom and C₁~ C₆1 selected from the group consisting of alkyl groups
It may be substituted with up to 5 substituents. ) 5 young
Is a 6-membered heterocyclic group (the heterocyclic group is a group consisting of 1 to 4 oxygen atoms
Containing a sulfur atom, a nitrogen atom, a halogen atom and
C₁~ C₆1 or 2 selected from the group consisting of alkyl groups
May be substituted. ), Cyano group, nitro
Group, amino group or phenoxy group (the phenoxy group is
Halogen atom and C₁~ C₆Select from the group consisting of alkyl groups
It may be substituted by 1 to 5 substituents. )
And n represents an integer of 1 to 5, X represents an oxygen atom, a sulfur atom, a sulfinyl group or a sulfo group.
Represents a nyl group;^FiveIs a hydrogen atom or C₁~ C₆Represents an alkyl group. ]so
The represented N-substituted amide compound. 21. The following general formula:[Wherein, R¹Is a hydrogen atom, C₁~ C₆Alkyl group <
An alkyl group has one C_Three~ C₇Cycloalkyl group, 1
(The phenyl group is a halogen atom and a C
₁~ C₆1 to 5 members selected from the group consisting of alkyl groups
It may be substituted by a substituent. ) One or two C₁~
C₆An alkoxy group (the alkoxy group may have 1 to 5
It may be substituted by a halogen atom. ) One C_Two~
C₆An alkenyloxy group, one (C₁~ C₆Alkoki
C) C₁~ C₆An alkoxy group, one benzyloxy group,
One C₁~ C₆Alkylthio group, 1 to 3 halogens
Atom, one cyano group, one di (C₁~ C₆Alkyl)
An amino group or one 5- or 6-membered heterocyclic group
The ring group has 1 to 4 oxygen, sulfur or nitrogen atoms
Containing a halogen atom and C₁~ C₆Alkyl group
Alkyl groups are substituted by one to three halogen atoms.
May be. 1) or 2 substitutions selected from the group consisting of
May be substituted by a group. Be replaced by｝
No. 》, C_Three~ C₇Cycloalkyl group, C_Two~ C₆Alkene
(The alkenyl group is one to three halogen atoms)
May be replaced by ), C_Two~ C₆Alkynyl group,
Phenyl group (the phenyl group is a halogen atom and a C₁~
C₆1 to 5 positions selected from the group consisting of alkyl groups
It may be substituted by a substituent. ) 5- or 6-membered heterocyclic ring
Group—the heterocyclic group has 1 to 4 oxygen atoms,
Or contains a nitrogen atom and contains one C₁~ C₆Alkyl group (this
The alkyl group is substituted by 1 to 3 halogen atoms
May be. ). ｝, C_Two~ C_Ten
Alkylcarbonyl group (the alkylcarbonyl group is
1 to 3 halogen atoms, 1 C₁~ C₆Alkoxy
Group or one phenoxy group. ),
A benzoyl group (the benzoyl group is a halogen atom and
C₁~ C₆1 to 5 selected from the group consisting of alkyl groups
May be substituted. ), C_Two~ C₈Alkoki
Carbonyl group, di (C₁~ C₆Alkyl) carbamoyl
Group, C₁~ C₆Alkylsulfonyl group or phenylsulfo
A phenyl group (the phenylsulfonyl group is a halogen atom and
And C₁~ C₆1 to 5 selected from the group consisting of alkyl groups
May be substituted. ), R^TwoAnd R^ThreeAre the same or different and are a hydrogen atom, C₁~ C₆
Alkyl group—the alkyl group has one C_Three~ C₇Cyclo
An alkyl group, one phenyl group (the phenyl group
Logen atom, C₁~ C₆Alkyl group and C₁~ C₆Alkoki
By 1 to 5 substituents selected from the group consisting of
It may be replaced. ) One or two C₁~ C₆Alkoxy
Group, one (C₁~ C₆Alkoxy) C₁~ C₆Alkoxy
Group, 1 to 13 halogen atoms or 1 5 or
6-membered heterocyclic group (the heterocyclic group is a group consisting of 1 to 4 oxygen atoms
Containing carbon, sulfur or nitrogen atoms. Replaced by
May be. ｝, C_Three~ C₇Cycloalkyl group, C_Two~ C₆A
A alkenyl group (the alkenyl group contains 1 to 3 halogen
May be substituted by a thiol atom. ), C_Two~ C₆Alkynyl
Group, phenyl group (the phenyl group is a halogen atom, C
₁~ C₆Alkyl group and C₁~ C₆Group consisting of alkoxy groups
Substituted with 1 to 5 substituents selected from
No. ) Or a 5- or 6-membered heterocyclic group.
Contains 1 to 4 oxygen, sulfur or nitrogen atoms
And a halogen atom and C₁~ C₆Alkyl group (the alkyl
May be substituted by 1 to 3 halogen atoms.
No. 1) or 2 substituents selected from the group consisting of
May be replaced. Represents｝, or R^TwoAnd R^ThreeIs
Together with the carbon atom to which they are attached, 4-7
Member, cycloalkane, cycloalkene or cyclo
Alkanediene ring—the ring is one to three C₁~ C₆A
Alkyl group, one C₁~ C₆An alkoxy group, one (C ₁
~ C₆Alkoxy) C₁~ C₆An alkoxy group, one di
(C₁~ C₆Alkyl) amino group, one C₁~ C_FourArchi
A dioxy group or one N- (C₁~ C₆Alkoxy)
May be substituted by an imino group, and at any position the ring is oxygen
Atom, sulfur atom or formula NR⁶A group represented by the formula:
⁶Is C₁~ C₆Represents an alkyl group. Interrupted by
May be. ｝, A is C₁~ C₆Alkyl group (the alkyl group is 1 to
It may be substituted by 13 halogen atoms. ),Halo
Gen atom, C₁~ C₆An alkoxy group (the alkoxy group
Is substituted by 1 to 5 halogen atoms.
No. ), C₁~ C₆Alkylthio group, C₁~ C₆Alkyls
Ruphonyl group, phenyl group (the phenyl group is halogen
Atom and C₁~ C₆1 selected from the group consisting of alkyl groups
It may be substituted with up to 5 substituents. ) 5 young
Is a 6-membered heterocyclic group (the heterocyclic group is a group consisting of 1 to 4 oxygen atoms
Containing a sulfur atom, a nitrogen atom, a halogen atom and
C₁~ C₆1 or 2 selected from the group consisting of alkyl groups
May be substituted. ), Cyano group, nitro
Group, amino group or phenoxy group (the phenoxy group is
Halogen atom and C₁~ C₆Select from the group consisting of alkyl groups
It may be substituted by 1 to 5 substituents. )
And n represents an integer of 1 to 5, X represents an oxygen atom, a sulfur atom, a sulfinyl group or a sulfo group.
Represents a nyl group. ] The N-substituted amide compound represented by this. 22. An agrochemical containing the N-substituted dihydropyrrole derivative according to any one of claims 1 to 19 as an active ingredient.