JP3294627B2 - Oxazoline compounds - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

The present invention relates to a novel oxazoline derivative exhibiting a strong herbicidal action, more specifically a 4-oxazoline-2-one derivative and a 4-oxazoline-2-thione derivative, and the compound as an active ingredient. Related to herbicides.

[0002]

2. Description of the Related Art Hitherto, as a 4-oxazolin-2-one derivative, a compound represented by the general formula:

[0003]

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The above publication describes a method for producing a 4-oxazolin-2-one derivative.

[0005]

However, in the above publication,
The substituent R ^{1 ′ at the} 5-position of the oxazoline ring is a methyl group,
Only the examples of an ethyl group, an n-propyl group, an i-propyl group, and a chloromethyl group are shown, and it is described that the herbicidal activity is effective. In addition, its activity is not sufficient at low application rates.

The inventors of the present invention have conducted intensive studies on the synthesis of oxazoline derivatives and their herbicidal activity over many years. We have found and completed the present invention.

[0007]

Configuration of the Invention

[0008]

The present invention provides a compound represented by the general formula (I):

[0009]

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Wherein R ¹ is a lower alkyl group, R ² is a lower alkyl group or a lower haloalkyl group, X is a hydrogen atom,
A halogen atom, a lower alkyl group or a lower alkylthio group, Y and Z are the same or different and are a hydrogen atom, a halogen atom, a lower alkyl group or a cyano group, W is an oxygen atom or a sulfur atom, R ³ is a hydrogen atom, a lower Alkyl group or formula-
A group represented by QR ⁴ , wherein Q is an oxygen atom or a sulfur atom, and R ⁴ is a hydrogen atom, a lower alkyl group, a cycloalkyl group, a lower alkenyl group, a lower alkynyl group, an acyl group, a lower alkoxycarbonyl group, Aryloxycarbonyl group, carbamoyl group, sulfamoyl group, lower alkylsulfonyl group,
An arylsulfonyl group, a di (lower alkoxy) phosphoryl group, a di (lower alkoxy) thiophosphoryl group, a tri (lower alkyl) silyl group, or the same or different one to three atoms selected from an oxygen atom, a sulfur atom and a nitrogen atom
5- to 8-membered saturated heterocyclic group containing two heteroatoms (R ⁴ represents 1 to 3 selected from the following substituent group A)
(Substituent group A) halogen atom, lower alkyl group, cycloalkyl group, hydroxyl group, oxo group, aryl group, aryloxy group, lower alkylthio group, arylthio group The same or different one selected from an acyl group, an acylamino group, an acyloxy group, a lower alkoxycarbonyl group, a cyano group, a hydroxyimino group, an oxygen atom and a nitrogen atom
A 4- to 6-membered saturated heterocyclic group containing 1 to 3 heteroatoms, a lower alkoxy group optionally substituted by halogen, nitro, lower alkoxy or carboxy lower alkyl, tri (lower alkyl) silyloxy group, lower alkyl A sulfonyloxy group and an arylsulfonyloxy group. ). And a herbicidal composition containing them as an active ingredient.

In the above, X, Y, Z and the substituent group A
"Halogen atom" in the definition of is fluorine, chlorine, bromine or iodine, preferably X, Y and the substituent A are fluorine or chlorine, Z is chlorine or bromine, more preferably,
X is chlorine, Y is fluorine, and Z is a chlorine atom.

In the above, R ¹ , R ² , R ³ , R ⁴ ,
The “lower alkyl group” in the definition of X, Y, Z and the substituent A is, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-
Butyl, n-pentyl, isopentyl, 2-methylbutyl, neopentyl, 1-ethylpropyl, n-hexyl, 4-methylpentyl, 3-methylpentyl, 2-methylpentyl, 1-methylpentyl, 3,3-dimethylbutyl, 1 to 6 carbon atoms such as 2,2-dimethylbutyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,3-dimethylbutyl, and 2-ethylbutyl a linear or branched alkyl group, preferably a straight or branched chain alkyl group having 1 to 3 carbon atoms, more preferably a methyl group or an ethyl group, R ¹ and R Most preferably in ² is a methyl group.

In the above, the “cycloalkyl group” in the definition of R ⁴ and the substituent group A is cyclopropyl,
A 3- to 10-membered saturated cyclic hydrocarbon group which may be condensed, such as cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, norbornyl and adamantyl, and preferably a 5- to 10-membered saturated cyclic hydrocarbon group; And more preferably a cyclopentyl or cyclohexyl group.

In the above, the “lower haloalkyl group” in the definition of R ² includes, for example, trifluoromethyl,
Trichloromethyl, difluoromethyl, dichloromethyl, dibromomethyl, fluoromethyl, chloromethyl,
Bromomethyl, iodomethyl, dibromochloromethyl,
2,2,2-trichloroethyl, 2,2,2-trifluoroethyl, 2-bromoethyl, 2-chloroethyl,
-Fluoroethyl, 2,2-dibromoethyl, 1,1-
Difluoroethyl, 1-chloro-1-fluoroethyl,
It is a group in which 1 to 3 identical or different “halogen atoms” are substituted for the “lower alkyl group” such as 3-chloropropyl and 3-bromopropyl.

In the above, the "lower alkoxy group" in the definition of the substituent group A includes, for example, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy,
Isobutoxy, s-butoxy, t-butoxy, n-pentoxy, isopentoxy, 2-methylbutoxy, neopentoxy, n-hexyloxy, 4-methylpentoxy, 3-methylpentoxy, 2-methylpentoxy,
The aforementioned “lower alkyl group” such as 3,3-dimethylbutoxy, 2,2-dimethylbutoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, and 2,3-dimethylbutoxy Is a straight-chain or branched-chain alkoxy group having 1 to 6 carbon atoms, preferably a straight-chain or branched-chain alkoxy group having 1 to 4 carbon atoms, bonded to an oxygen atom.

The "lower alkoxy group" may be substituted by 1 to 3 identical or different halogen, nitro, lower alkoxy or carboxy lower alkyl, for example, trifluoromethoxy, chloromethoxy, methoxymethoxy , Methoxy ethoxy, ethoxy ethoxy and the like.

In the above, the "lower alkenyl group" in the definition of R ⁴ includes, for example, vinyl, 1-propenyl, 2-propenyl, 1-methyl-2-propenyl, 2
-Methyl-2-propenyl, 2-ethyl-2-propenyl, 2-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 1-ethyl-2-butenyl, 3-
Butenyl, 1-methyl-3-butenyl, 2-methyl-3
-Butenyl, 1-ethyl-3-butenyl, 2-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl , 4-pentenyl, 1
A straight-chain or branched alkenyl group having 2 to 6 carbon atoms, such as -methyl-4-pentenyl, 2-methyl-4-pentenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl; is there.

In the above, the “lower alkynyl group” in the definition of R ⁴ means ethynyl, 2-propynyl, 1-
Methyl-2-propynyl, 1-ethyl-2-propynyl, 2-butynyl, 1-methyl-2-butynyl, 2-methyl-2-butynyl, 1-ethyl-2-butynyl, 3-
Butynyl, 1-methyl-3-butynyl, 2-methyl-3
-Butynyl, 1-ethyl-3-butynyl, 2-pentynyl, 1-methyl-2-pentynyl, 2-methyl-2-pentynyl, 3-pentynyl, 1-methyl-3-pentynyl, 2-methyl-3-pentynyl , 4-pentynyl, 1
-Methyl-4-pentynyl, 2-methyl-4-pentynyl,
2-hexynyl, 3-hexynyl, 4-hexynyl, 5
-A straight-chain or branched alkynyl group having 2 to 6 carbon atoms, such as hexynyl.

In the above, the term "acyl group" in the definition of R ⁴ and the substituent group A means, for example, a lower alkylcarbonyl group such as acetyl, propionyl, butyryl and isobutyryl; an aryl group such as benzoyl and α-naphthoyl. Aromatic acyl groups such as carbonyl groups; at least one to three oxygen atoms, sulfur atoms or nitrogen atoms such as furyl, thienyl, pyrrolyl, pyridyl, thiazolyl, isothiazolyl, oxazolyl, imidazolyl and pyrazolyl;
It is a 5- or 6-membered heterocyclic acyl group which contains, preferably an alkylcarbonyl group, and more preferably an acetyl group.

In the above, the “acylamino group” in the definition of the substituent group A is a group in which one of the above “acyl groups” is bonded to an amino group, preferably an alkylcarbonylamino group, more preferably Is an acetylamino group.

In the above, the “acyloxy group” in the definition of the substituent group A is a group in which the above “acyl group” is bonded to an oxygen atom, preferably an alkylcarbonyloxy group, more preferably , An acetyloxy group.

In the above, “lower alkoxycarbonyl group” in the definition of R ⁴ and the substituent group A includes, for example, methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, isopropoxycarbonyl, n-
Such a “lower alkoxy group” is a group bonded to a carbonyl group, such as butoxycarbonyl, s-butoxycarbonyl, and isobutoxycarbonyl group.

In the above, the “aryl group” in the definition of the substituent group A includes, for example, phenyl, indenyl,
It is an aromatic hydrocarbon group having 5 to 14 carbon atoms, such as naphthyl, phenanthrenyl and anthracenyl, and is preferably a phenyl group.

In the above, the “aryloxy group” in the definition of the substituent group A is a group in which the above “aryl group” is bonded to an oxygen atom, and is preferably a phenyloxy group.

In the above, the “aryloxycarbonyl group” in the definition of R ⁴ is a group in which the above “aryloxy group” is bonded to a carbonyl group, and is preferably phenyloxycarbonyl.

In the above, the “lower alkylsulfonyl group” in the definition of R ⁴ is the above “lower alkyl group”
Is a group bonded to a sulfonyl group.

In the above, the “arylsulfonyl group” in the definition of R ⁴ is a group in which the above “aryl group” is bonded to a sulfonyl group.

In the above, the “lower alkylthio group” in the definition of X and the substituent group A is a group in which the above “lower alkyl group” is bonded to a sulfur atom.

In the above, the “arylthio group” in the definition of the substituent group A is a group in which the above “aryl group” is bonded to a sulfur atom.

In the above, the term “4- to 6-membered saturated heterocyclic group containing 1 to 3 identical or different hetero atoms selected from oxygen and nitrogen atoms” in the definition of the substituent A means, for example, oxetanyl , Morpholinyl, thiomorpholinyl, pyrrolidinyl, pyrrolinyl, imidazolidinyl, imidazolinyl, oxazolidinyl, pyrazolidinyl, pyrazolinyl, piperidyl, piperazinyl,
It is a 4- to 6-membered saturated heterocyclic group containing 1 to 3 oxygen atoms and / or nitrogen atoms, such as thiazolidinyl, tetrahydropyranyl, (2,2-dimethyl) -1,3-dioxolanyl.

In the above, “di (lower alkoxy) phosphoryl group” and “di (lower alkoxy) thiophosphoryl group” in the definition of R ⁴ are the same or different.
The above “lower alkoxy groups” are groups bonded to a phosphoryl group or a thiophosphoryl group, respectively.

In the above, the “tri (lower alkyl) silyl group” in the definition of R ⁴ means, for example, three identical or different “lower alkyl” groups such as trimethylsilyl, t-butyldimethylsilyl and triethylsilyl. "Group" refers to a group bonded to silyl, and is preferably a trimethylsilyl, t-butyldimethylsilyl, or triethylsilyl group.

In the above, in the definition of R ⁴ , “a 5- to 8-membered saturated heterocyclic group containing the same or different 1 to 3 hetero atoms selected from an oxygen atom, a sulfur atom and a nitrogen atom” includes, for example, , Tetrahydrofuranyl,
Tetrahydropyranyl, hexahydrooxepinyl,
At least one oxygen atom, sulfur atom or nitrogen atom such as 1,3-dioxanyl, 1,4-dioxanyl, tetrahydrothiofuranyl, pyrrolidinyl, piperidinyl, morpholinyl, tetrahydrofurano [3,2-b] tetrahydrofuranyl; It is a 5- to 8-membered fully saturated heterocyclic group containing 3 and is preferably tetrahydrofuranyl, tetrahydropyranyl or tetrahydrofurano [3,2-b] tetrahydrofuranyl.

In the above, the “carboxy lower alkyl group” in the definition of the substituent A is a group in which one carboxy group is substituted by the above “lower alkyl group”, such as carboxymethyl and 2-carboxyethyl. is there.

In the above, “substituted by an oxo group” in the definition of the substituent A means that a methylene group is bonded to an oxo group to form a carbonyl group.

In the above, “substituted by a hydroxyimino group” in the definition of the substituent A means that a methylene group is bonded to a hydroxyimino group to form an oxime group.

In the above, the “tri (lower alkyl) silyloxy group”, “lower alkylsulfonyloxy group” and “arylsulfonyloxy group” in the definition of the substituent A are the above “tri (lower alkyl) silyl group”, An oxygen atom is bonded to each of the “lower alkylsulfonyl group” and the “lower alkylsulfonyl group”.

When the compound of the present invention has an asymmetric carbon in the molecule, the compound may have an R configuration or an S configuration with respect to the asymmetric carbon. Accordingly, the present invention includes the respective isomers and mixtures thereof in any proportion.

When two or more asymmetric carbons are present and the relative configuration between the asymmetric carbons is limited, isomers having different relative configurations may exist.

In Table 1 below, unless otherwise specified, the mixture is a mixture for asymmetric carbon.

In Table 1, those having one asymmetric carbon and having a clear configuration are described as having the "R" or "S" configuration.

When two asymmetric carbons are present, two isomers having different relative configurations may exist. Generally, the physicochemical properties of these compounds are different, and in such a case, the compounds shown in Table 1 are described as “isomer A” or “isomer B”.

When three asymmetric carbons are present, there may be four isomers having a limited relative configuration. When the compounds described in Table 1 are such, they are described as “isomer A”, “isomer B”, “isomer C” and “isomer D”.

In the above general formula (I), R ¹ is preferably a methyl group.

In the general formula (I), R ² is preferably a lower alkyl group, more preferably a methyl group.

In the above general formula (I), X is preferably a halogen atom, more preferably a chlorine atom.

In the above general formula (I), Y is preferably a halogen atom, more preferably a fluorine atom.

In the above formula (I), Z is preferably a halogen atom, more preferably a chlorine atom.

In the above general formula (I), W is preferably an oxygen atom.

In the general formula (I), R ³ is preferably a group represented by the formula —QR ⁴ .

In the above general formula (I), Q is preferably an oxygen atom.

In the general formula (I), R ⁴ is preferably a lower alkyl group, a lower alkynyl group, or one to three hetero atoms selected from the group consisting of oxygen, sulfur and nitrogen. And more preferably a lower alkyl group, a lower alkynyl group or a 5- to 8-membered saturated heterocyclic group containing one or two oxygen atoms. More preferably, it is a lower alkynyl group or a 5- or 6-membered saturated heterocyclic group containing one oxygen atom.

At this time, the substituent group A is preferably a lower alkyl group or a lower alkoxy group which may be substituted with one lower alkoxy, and more preferably a methyl group, an ethyl group, A methoxy group, an ethoxy group, a methoxyethoxy group or an ethoxyethoxy group, more preferably a methyl group or a methoxy group.

Among the compounds of the present invention, (1) In formula (I), R ¹ is a lower alkyl group, R ² is a lower alkyl group, X is a hydrogen atom, a halogen atom, a lower alkyl group or a lower alkylthio group. The group, Y and Z are the same or different and each is a hydrogen atom, a halogen atom, a lower alkyl group or a cyano group, W is an oxygen atom, R ³ is a hydrogen atom, a lower alkyl group or a group represented by the formula -QR ⁴ (wherein , Q is an oxygen atom or a sulfur atom, R ⁴ is a hydrogen atom, a lower alkyl group, a cycloalkyl group, a lower alkenyl group, a lower alkynyl group, an acyl group, a lower alkoxycarbonyl group, an aryloxycarbonyl group, a carbamoyl group, a sulfamoyl group, Di (lower alkoxy)
A phosphoryl group, a di (lower alkoxy) thiophosphoryl group, or a 5- to 8-membered saturated heterocyclic group containing 1 to 3 identical or different hetero atoms selected from oxygen, sulfur and nitrogen, (R ⁴ May be substituted with 1 to 3 identical or different substituent (s) selected from Substituent Group A), wherein Substituent Group A is a halogen atom, a lower alkyl group, a cycloalkyl group, a hydroxyl group, an oxo group. ,
Aryl group, aryloxy group, lower alkylthio group,
4 to 6 members containing 1 to 3 same or different 1 to 3 hetero atoms selected from arylthio, acyl, acylamino, acyloxy, lower alkoxycarbonyl, cyano, hydroxyimino, oxygen and nitrogen An oxazoline derivative which is a saturated heterocyclic group and a lower alkoxy group which may be substituted with halogen, nitro, lower alkoxy or carboxy lower alkyl), more preferably (2) in the general formula (I), R ¹ is lower Alkyl group, R ² is lower alkyl group, X is hydrogen atom, halogen atom or lower alkyl group, Y and Z are the same or different and hydrogen atom, halogen atom, lower alkyl group or cyano group, W is oxygen atom, R ³ but a hydrogen atom, a lower alkyl group or a group (wherein the formula -QR ^4, Q is an oxygen atom, R ⁴ is hydrogen Hara The same or different 1 to 3 groups selected from the group consisting of an oxygen atom, a sulfur atom and a nitrogen atom, a lower alkyl group, a cycloalkyl group, a lower alkenyl group, a lower alkynyl group, an acyl group, a lower alkoxycarbonyl group, an aryloxycarbonyl group; 5- to 8-membered saturated heterocyclic group containing two hetero atoms (R ⁴ may be substituted by 1 to 3 identical or different substituent (s) selected from Substituent Group A), a substituent Group A is the same or different one to three selected from a halogen atom, a lower alkyl group, a cycloalkyl group, an oxo group, an acyl group, an acylamino group, an acyloxy group, a lower alkoxycarbonyl group, a cyano group, an oxygen atom and a nitrogen atom. 4- to 6-membered saturated heterocyclic group containing two heteroatoms and halogen, nitro, lower alkoxy or An oxazoline derivative which is a lower alkoxy group optionally substituted with a boxy lower alkyl), more preferably (3) in the general formula (I), R ¹ is a methyl group, R ² is a methyl group, X is a hydrogen atom or A halogen atom, Y and Z are the same or different, a halogen atom or a cyano group, W is an oxygen atom, R ³ is a hydrogen atom, a lower alkyl group or a group represented by the formula —QR ⁴ (wherein Q is an oxygen atom , R ⁴ is a 5- to 8-membered saturated complex containing 1 to 3 identical or different hetero atoms selected from a hydrogen atom, a lower alkyl group, a lower alkynyl group, a lower alkoxycarbonyl group, or an oxygen atom and a sulfur atom; Ring group,
(R ⁴ may be substituted by 1 to 3 identical or different substituents selected from Substituent Group A.) When Substituent Group A is a halogen atom, a lower alkyl group, a cycloalkyl group, an oxo group, Group, acyl group, acylamino group, acyloxy group, lower alkoxycarbonyl group, cyano group,
Or a 4- to 6-membered saturated heterocyclic group containing 1 to 3 oxygen atoms and a lower alkoxy group optionally substituted with halogen, lower alkoxy or carboxy lower alkyl)
More preferably, the oxazoline derivative represented by the formula: (4) In the general formula (I), R ¹ is a methyl group, R ² is a methyl group, X is a hydrogen atom, a fluorine atom or a chlorine atom, and Y and Z are the same or different. A fluorine atom, a chlorine atom, a bromine atom or a cyano group, W is an oxygen atom, R ³ is a group represented by the formula —QR ⁴ (wherein Q is an oxygen atom, R ⁴ is a hydrogen atom, a lower alkyl group, Lower alkynyl group or 5 to 8 containing 1 to 2 oxygen atoms
Membered heterocyclic group, wherein R ⁴ is 1 selected from substituent group A
Substituent group A may be a halogen atom, a lower alkyl group, a lower alkoxycarbonyl group, or 5-6 containing 1 to 3 oxygen atoms. Oxazoline derivatives, which are membered saturated heterocyclic groups and lower alkoxy groups which may be substituted with halogen or lower alkoxy), more preferably (5) in the general formula (I), R ¹ is a methyl group, R ² Is a methyl group, X is a fluorine atom or a chlorine atom, Y and Z are the same or different, a fluorine atom,
A chlorine atom, a bromine atom or a cyano group, W is an oxygen atom, R ³
Is a group represented by the formula —QR ⁴ (wherein Q is an oxygen atom, R ⁴
Is a hydrogen atom, a lower alkyl group, a lower alkynyl group, or a 5- to 8-membered saturated heterocyclic group containing 1 to 2 oxygen atoms, wherein R ⁴ is 1 to 3 members selected from substituent group A May be substituted with the same or different substituents), and the substituent group A may be substituted with a fluorine atom, a chlorine atom, a methyl group, an ethyl group, a methoxycarbonyl group, an ethoxycarbonyl group, and a lower alkoxy group. An oxazoline derivative which is a preferable lower alkoxy group), and more preferably (6) in the general formula (I), R ¹ is a methyl group, R ² is a methyl group, X is a chlorine atom, Y is a fluorine atom or a chlorine atom, Z is a chlorine atom, bromine atom or cyano group, W is an oxygen atom, R ³ is a group represented by the formula —QR ⁴ (wherein Q is an oxygen atom, R ⁴ is a methyl group, an ethyl group,
Isopropyl group, s-butyl group, 2-propynyl group, 1-methyl-2-propynyl group, tetrahydrofuranyl group, tetrahydropyranyl group or tetrahydrofurano [3,2-
b] a tetrahydrofuranyl group, wherein R ⁴ may be substituted by one or two identical or different substituents selected from substituent group A, wherein substituent group A is a chlorine atom, a methyl group, A methoxycarbonyl group, an ethoxycarbonyl group, a methoxy group optionally substituted with a methoxy group or an ethoxy group, and an ethoxy group optionally substituted with a methoxy group or an ethoxy group), more preferably an oxazoline derivative, (7) In the general formula (I), R ¹ is a methyl group, R ² is a methyl group, X is a chlorine atom, Y is a fluorine atom, Z is a chlorine atom, W is an oxygen atom, and R ³ is a formula-
A group represented by QR ⁴ (wherein Q is an oxygen atom, R ⁴ is a methyl group, a 2-propynyl group, a 1-methyl-2-propynyl group, a tetrahydrofuranyl group or a tetrahydropyranyl group,
(R ⁴ may be substituted by one or two identical or different substituents selected from Substituent Group A), wherein Substituent Group A is a methyl group, a methoxy group, a methoxymethoxy group, a methoxyethoxy group. Oxazoline derivatives which are ethoxyethoxy groups and ethoxymethoxy groups).

Hereinafter, the compounds of the present invention are shown in Table 1 together with the compound numbers, but the present invention is not limited to these compounds.

In Table 1, Me is methyl, Et is ethyl,
nPr is n-propyl, iPr is isopropyl, cPr is cyclopropyl, iBu is isobutyl, nBu is n-butyl, sB
u is s-butyl, tBu is t-butyl, cBu is cyclobutyl, cPn cyclopentyl, nHx is n-hexyl, cHx is cyclohexyl, cHp is cycloheptyl, nOx is n-octyl, oxo is oxo, Ph is phenyl, Bz Is benzyl, Vin is vinyl, All is allyl, Etn is ethynyl, Pr
g is propargyl, Pyrd is pyrrolidinyl, Thf is tetrahydrofuranyl, Thp is tetrahydropyranyl, Dxa is 1,3-dioxanyl, Dxl is 1,3-dioxolanyl, Mor is morpholino, Imid is imidazolyl, and Triz is 1,2,4. - triazolyl, Pyr is pyridyl, Thi thienyl, Fur furanyl, OXT oxetanyl, Thtp is tetrahydrothiopyranyl, Thtf the tetrahydrothiofuranyl, 1E1MPr is (1-ethyl-1-methyl) propyl, 1CHF ₂ 1ME is (1-difluoromethyl-1-methyl)
Ethyl, 1CH ₂ F1ME is (1-fluoromethyl-1-methyl) ethyl, 1CH ₂ Cl1ME is (1-chloromethyl-1-methyl) ethyl, 1CHCl ₂ 1ME is (1-dichloromethyl-1
—Methyl) ethyl, 1CF ₃ 1ME represents (1-trifluoromethyl-1-methyl) ethyl, and Thf [3,2-b] Thf represents a tetrahydrofurano [3,2-b] tetrahydrofuranyl group.

For example, O (1-Me) Prg is a 1-methylpropargyloxy group, OCH ₂ S (4-Cl) Ph is a 4-chlorophenylthiomethyloxy group, and 2 = N-OH is 2-hydroxyimino Represents a group.

[0058]

[Table 1]

[0059]

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──────────────────────────────────── Compound No. RWXYZR ³ melting point (° C.) ─── ───────────────────────────────── 1 tBu OHH Cl H 172-174 2 tBu OHHFH 159.5-162 3 tBu OH Cl Cl H 804 tBu OH Cl Cl OiPr 89-92 5 tBu OFHFH 76-79.5 6 tBu O Cl H Cl H 86-87 7 tBu O Cl Cl Cl H 85-86.5 8 tBu O Cl Cl Cl OiPr 101-103 9 tBu OHH CN H 162.5-165.5 10 tBu O Cl H CN H 176.5-178 11 tBu OHF Cl H NMR (oil) 12 tBu O Cl F Cl H 95-97 13 tBu OHF Cl OCH ₂ OCH ₂ CH ₂ OMe NMR (oil ) 14 tBu O Cl F Cl OCH ₂ OCH ₂ CH ₂ OMe NMR (oil) 15 tBu O Cl F Cl OH 170-171.5 16 tBu O Cl F Cl OPrg 83-85 17 tBu O Cl FFH 72-74 18 tBu OHFFH 52 -54 19 tBu SHFFH 115-119 20 tBu S Cl FFH 115-118 21 tBu O Cl F Cl OCH ₂ COOEt NMR (oil) 22 tBu O Cl F Cl OAll 82-86 23 tBu O Cl F Cl OCH (Me) COOEt 88- 88.5 24 tBu O Cl F Cl OiPr 78.5-80.0 25 tBu OHFF OCH ₂ OCH ₂ CH ₂ OMe NMR (oil) 26 tBu OH Cl Cl OCH ₂ OCH ₂ CH ₂ OMe NMR (oil) 27 tBu O Cl Cl Cl OCH ₂ OCH ₂ CH ₂ OMe NMR (oil) 28 tBu O Cl FF OCH ₂ OCH ₂ CH ₂ OMe NMR (oil) 29 tBu O Cl Cl Cl OH 175-178 30 tBu O Cl FF OH 118-121 31 tBu O Cl Cl Cl OPrg 121 32 tBu O Cl FF OPrg 115-116 33 tBu O Cl F Cl O (1-Me) Prg 113-114 34 tBu O Cl F Cl OCH (Me) COOH 159-164 35 tBu O Cl F Cl OCH ₂ SMe NMR (Oil) 36 tBu O Cl F Cl OCH (Me) Ph 121-122 37 tBu O Cl F Cl O (2-Me) All 61-61.5 38 tBu O Cl F Cl OCH ₂ 2-Pyr 129-134 39 tBu O Cl F Cl OEt 88-90 40 tBu O Cl F Cl OCHF ₂ 56-58 41 tBu OHF Br H NMR (oil) 42 tBu O Cl F Br H 62-64 43 tBu O Cl Cl Cl OCH (Me) COOEt 89.5 44 tBu O Cl Cl Cl OCH ₂ COOEt 81-83 45 tBu O Cl Cl Cl OAll 62-64 46 tBu OHF Br OCH ₂ OCH ₂ CH ₂ OMe NMR (oil) 47 tBu O Cl F Br OCH ₂ OCH ₂ CH ₂ OMe NMR (Oil) 48 tBu O Cl F Br OH 182-183.5 49 tBu O Cl F Br OPrg NMR (oil) 50 tBu OH Cl F OCH ₂ OCH ₂ CH ₂ OMe NMR (oil) 51 tBu O Cl Cl F OCH ₂ OCH ₂ CH ₂ OMe NMR (oil) 52 tBu O Cl Cl F OH 164-166 53 tBu O Cl Cl F OPrg 108-109 54 tBu O Cl F Cl OMe 94-96 55 tBu O Cl F Cl OCH ₂ CH ₂ OMe 58 56 tBu O Cl F Cl OCH ₂ CH ₂ OEt 63-64 57 tBu O Cl F Cl OCH ₂ CN 86-87 58 tBu O Cl F Cl OCH ₂ OMe 98-99 59 tBu O Cl Cl Cl OMe 124-124.5 60 tBu O Cl Cl Cl OEt 88-89 61 tBu O Cl Cl Cl OCH ₂ SMe 92-93 62 tBu O Cl F Cl OCH ₂ CH ₂ OPh 114-115 63 tBu O Cl Cl Cl OCH ₂ CN 109-111 64 tBu O Cl Cl Cl OCH ₂ OMe 98 65 tBu O Cl F Cl OCH ₂ CF ₃ 89-92 66 tBu O Cl Cl Cl OCH ₂ CH ₂ OEt NMR (oil) 67 1E1MPr OHF Cl H 94-96 68 1E1MPr O Cl F Cl H NMR (oil) 69 tBu O Cl F Cl OCH (Me) CON (Me) ₂ 153-153.5 70 tBu O Cl F Cl OCH ₂ (4-NO ₂ ) Ph 185-187 71 tBu O Cl F Cl OCH ₂ S (4-Cl) Ph NMR (amorphous) 72 tBu O Cl F CN OiPr 177-179 7 tBu O Cl F CN OEt 75 74 tBu O Cl F Cl OCH 2 SPh NMR ( _{oil) 75 1E1MPr OHF Cl OCH 2 OCH} 2 CH 2 OMe NMR ( oil) 76 1E1MPr O Cl F Cl OCH 2 OCH 2 CH 2 OMe 47- 49 77 1E1MPr O Cl F Cl OH 139-141 78 1E1MPr O Cl F Cl OPrg 68-69 79 tBu O Cl F Cl OCH ₂ CH ₂ Cl 55-57 80 tBu OHF Cl OCH ₂ OMe 79-81 81 tBu O Cl F Cl OCH ₂ CH ₂ OCH ₂ CH ₂ Cl NMR (oil) 82 tBu O Cl F Cl OCH ₂ cPr 77-80 83 tBu O Cl F Cl OCH ₂ CH ₂ OCH ₂ CH ₂ OMe NMR (oil) 84 tBu O Cl F Cl OCH ₂ OBz NMR (oil) 85 tBu O Cl F Cl OCH ₂ SCH ₂ CH ₂ Cl 86 tBu O Cl F Cl OCH ₂ CH (OEt) ₂ 44-46 87 tBu O Cl F Cl OCH ₂ CH ₂ OVin NMR ( (Oil) 88 tBu O Cl F Cl OCH ₂ OCH ₂ CCl ₃ 89 tBu O Cl F Cl OCH ₂ OCH ₂ F 90 tBu O Cl F Cl OCH ₂ OCH ₂ Cl 91 tBu O Cl F Cl OCH ₂ OCH ₂ CH ₂ F 92 tBu O Cl F Cl OCH ₂ OCH ₂ CH ₂ Cl 93 tBu O Cl F Cl OCOMe 94 tBu O Cl F Cl OCOOEt 122-127 95 tBu O Cl F Cl OCOOCH ₂ CCl ₃ 126-130 96 tBu O Cl F Cl OCOOPh 97 tB u O Cl F Cl OCON (Me) ₂ NMR (cam) 98 tBu O Cl F Cl OSO ₂ N (Me) ₂ NMR (cam) 99 tBu O Cl F Cl OCON (Et) ₂ 100 tBu O Cl Cl Cl OSO ₂ N (Me) ₂ 101 tBu O Cl Cl Cl OCON (Me) ₂ 102 tBu O Cl F Cl OCOOCH ₂ CH ₂ OMe 103 tBu O Cl F Cl OCH ₂ COMe 97-102 104 tBu O Cl F Cl OCH (Me ) CH ₂ OCOMe 105 tBu O Cl F Cl OCH ₂ CH ₂ 2- (N-Me) Pyrd NMR (oil) 106 tBu O Cl F Cl OCH ₂ 3-Thp 107 tBu O Cl F Cl OCH ₂ 4- (2, 2-Me ₂ ) Dxl 115-118 108 tBu O Cl F Cl OCH ₂ 3-Thf 109 tBu O Cl F Cl OCH ₂ CH ₂ 3-Thf 110 tBu O Cl F Cl OCH ₂ CH ₂ NHCOMe 111 tBu O Cl F Cl _{OCH (Me) CH 2 OH 112} tBu O Cl F Cl OCH 2 CH 2 N-Mor 62-66 113 tBu O Cl F Cl OCH 2 CH 2 N-Imid 114 tBu O Cl F Cl OCH 2 1-Triz 115 tBu O Cl F Cl OSO ₂ Me 116 tBu O Cl F Cl OSO ₂ CH ₂ Cl 89-91 117 tBu O Cl F Cl OSO ₂ Et 79-82 118 tBu O Cl F Cl OSO ₂ CH ₂ (2-Cl) Ph 119 tBu O Cl F Cl OSO ₂ (4-Me) Ph 174-176 120 1CHF ₂ 1ME OHF Cl OCH ₂ OCH ₂ CH ₂ OMe 121 1CHF ₂ 1ME OHF Cl H 122 1CHF ₂ 1ME O Cl F Cl H 123 tBu O Cl F Br OEt 87-87.5 124 tBu O Cl F Br OiPr 82-83 125 tBu O Cl F Br OCH ₂ OMe 126 tBu O Cl F Br OCH ₂ CH ₂ OEt 127 1CHF ₂ 1ME OHF Cl H 128 tBu O Cl F Cl OCH ₂ CH ₂ OH NMR (oil) 129 1CHF ₂ 1ME O Cl F Cl OH 130 1CHF ₂ 1ME O Cl F Cl OPrg 131 1CHF ₂ 1ME O Cl F Cl OCH ₂ OCH ₂ CH ₂ OMe 132 1CHF ₂ 1ME OHF Cl OCH ₂ OCH ₂ CH ₂ OMe 133 tBu O Cl F Cl OCH ₂ CH ₂ F NMR (oil) 134 1CHF ₂ 1ME O Cl F Cl OCH ₂ OMe 135 1CHF ₂ 1ME O Cl F Cl OCH ₂ CH ₂ OEt 136 tBu OHF Cl OCH ₂ OPrg 137 tBu O Cl F Cl OCH ₂ OPrg 138 tBu O Cl Cl Cl OCH ₂ OPrg 139 tBu O Cl F Cl OCH ₂ O (1-Me) Prg 140 tBu O Cl Cl Cl OCH ₂ O (1-Me) Prg 141 tBu OHF Cl OCH ₂ CH ₂ OPrg 142 tBu O Cl F Cl OCH ₂ CH ₂ OPrg 143 tBu O Cl Cl Cl OCH ₂ CH ₂ OPrg 144 tBu O Cl F Cl OCH ₂ CH ₂ O (1-Me) Prg 145 tBu O Cl Cl Cl OCH ₂ CH ₂ O (1-Me) Prg 146 tBu OHF Cl OCH ₂ CH ₂ OCH ₂ CH ₂ OMe 147 tBu O Cl Cl Cl OCH ₂ CH ₂ OCH ₂ CH ₂ OMe 148 tBu OH Cl Cl OCH ₂ CH ₂ OCH ₂ CH ₂ OMe 149 tBu O Cl Cl Cl O (1-Me) Prg 150 tBu OH Cl Cl O (1-Me) Prg 151 tBu OHF Cl O (2-Br) All 152 tBu O Cl F Cl O (2-Br) All 78- 81 153 tBu O Cl F Cl OCH ₂ OAll 154 tBu O Cl F Cl OCH ₂ O (2-Me) All 155 tBu O Cl F Cl OCH ₂ CH ₂ OAll 156 tBu O Cl F Cl OCH ₂ CH ₂ O (2- Me) All 157 tBu OHF Me H 158 tBu O Cl F Me H 159 tBu O Cl F Me OH 160 tBu O Cl F Me OCH ₂ OCH ₂ CH ₂ OMe 161 tBu O Cl F Me OPrg 162 tBu O Cl F Me O ( 1-Me) Prg 163 tBu O Cl F Me OCH ₂ OMe 164 tBu O Cl F Me OCH ₂ CH ₂ OEt 165 1CH ₂ F1ME O Cl F Cl OPrg 166 1CH ₂ Cl1ME O Cl F Cl OPrg 167 1CHCl ₂ 1ME O Cl F Cl OPrg 168 1CF ₃ 1ME O Cl F Cl OPrg 169 1CH ₂ Cl1ME O Cl F Cl OH 170 1CH ₂ F1ME O Cl F Cl OH 171 tBu O Cl F Cl O (cPr) 172 tBu O Cl F Cl O (cBu) 113 -114 173 tBu O Cl F Cl O (cPn) 94-96 174 tBu O Cl F Cl O (cHx) 122-125 175 tBu O Cl Cl Cl O (cPn) 176 tBu O Cl Cl Cl O (cHx) 177 tBu O Cl F Cl OCH ₂ CH ₂ OCH ₂ CH ₂ OEt NMR (oil) 178 tBu OHF Cl OCH ₂ CH ₂ OCH ₂ CH ₂ OEt 179 tBu O Cl F Cl OCOCH ₂ Cl 180 tBu O Cl F Cl OCOCH ₂ Br NMR (oil) 181 tBu O Cl F Cl CH ₃ 48-50 182 tBu OHF Cl CH ₃ 67-72 183 tBu OHF Cl OCH ₂ OEt 69-70 184 tBu O Cl F Cl OCH ₂ (2-Dxl) NMR (cam-like) 185 tBu O Cl F Cl OCH ₂ CH ₂ Br 68-71 186 tBu O Cl F Cl OCH ₂ (2-Thp) 139-140 187 tBu O Cl Cl Cl OCH ₂ (2-Thp) 188 tBu O Cl F Cl OCH ₂ COPh 135-137 189 tBu O Cl Cl Cl OCH ₂ COPh 190 tBu O Cl F Cl OCH ₂ CO (4-Cl) Ph 166-168 191 tBu O Cl Cl Cl OCH ₂ CO (4-Cl) Ph 192 tBu O Cl F Cl OCH ₂ CO (4-F) Ph 193 tBu O Cl Cl OCH ₂ CO (4-F) Ph 194 tBu O Cl F Cl OCOCH ₂ OPrg 119-121 195 tBu O Cl F Cl OCOtBu 155-160 196 tBu O Cl F Cl OCOPh 105-110 19 tBu O Cl F Cl OCO (4 -Cl) Ph 110-115 198 tBu O Cl F Cl OCH 2 CH 2 SEt NMR ( oil) 199 tBu OHF Cl OPrg 142-143 200 tBu O Cl F Cl OCOCH 2 CH 2 CH 2 COOMe NMR (oil) 201 tBu O Cl F Cl OCH ₂ CH ₂ (2-Dxa) NMR (oil) 202 tBu O Cl F Cl O (4-Thp) 68-70.5 203 tBu O Cl F Cl OCH ₂ CH ₂ OnPr NMR (oil) 204 tBu O Cl F Cl OCH ₂ cHx 124-127 205 tBu O Cl F Cl OCH ₂ CH ₂ OiPr NMR (oil) 206 tBu O Cl F Cl OCH ₂ CH ₂ OCH ₂ CH ₂ OnBu NMR (oil) 207 tBu O Cl F Cl OCH ₂ CH ₂ CH (OEt) ₂ NMR (oil) 208 tBu O Cl F Cl OcHp 115-124 209 tBu O Cl F Cl O (CH ₂ ) ₃ [2- (2-Me) Dxl ] 91-95 210 tBu O Cl F Cl OnPr 76-76.5 211 tBu O Cl F Cl OnBu 58-60 212 tBu O Cl F Cl OCH ₂ Prg 54-57 213 tBu O Cl F Cl O (3-MePrg) 112- 115 214 tBu O Cl F Cl O (2-Thf) NMR (oil) 215 tBu O Cl F Cl OCO (2-Thi) NMR (oil) 216 tBu O Cl F Cl OSO ₂ nPr NMR (oil) 217 tBu O Cl F Cl OCOFur NMR 218 tBu O Cl F Cl OSi (Me) ₂ tBu 115-118 219 tBu O Cl F Cl OPO (OEt) ₂ NMR (oil) 220 tBu O Cl F Cl OPS (OEt) ₂ NMR (oil) 221 tBu O Cl F Cl OCH ₂ CH ₂ (2-Dxl) NMR (oil) 222 tBu O Cl F Cl OCH ₂ CH ₂ OCH ₂ CH ₂ OnHx NMR (oil) 223 tBu O Cl F Cl OCH ₂ CH ₂ OCH ₂ CH ₂ OiBu NMR (oil) 224 tBu O Cl F Cl OCSN (Me) ₂ NMR (oil) 225 tBu O Cl F Cl O (3-Thf) ₂ 114-115 226 tBu O Cl F Cl OCO Vin 82 227 tBu O Cl F Cl OCH (Me) CH ₂ OMe NMR (oil) 228 tBu O Cl F Cl OCH ₂ All NMR (oil) 229 tBu O Cl F Cl OCH ₂ OnOx NMR (oil) 230 tBu O Cl F Cl OCH ₂ CH (OMe) ₂ NMR (oil) 231 tBu O Cl F Cl O (2-Thp) NMR ( oil) 232 tBu O Cl F Cl OCH (Me) COCH 3 88-89 233 tBu O SEt F Cl H NMR ( oil) 234 tBu O SEt F Cl OCH ₂ OCH ₂ CH ₂ OMe NMR (oil) 235 tBu O SEt F Cl OH 65-67 236 tBu O SiPr F Cl OH 164-165 237 tBu O SEt F Cl OPrg NMR (oil) 238 tBu O SE t F Cl OCH ₂ OMe NMR (oil) 239 tBu O Cl F Cl OsBu NMR (oil) 240 tBu O Cl F Cl OiBu 80-85 241 tBu O SiPr F Cl OPrg NMR (oil) 242 tBu O SiPr F Cl OCH ₂ OMe 90-92 243 tBu O SnPr F Cl OPrg 85-90 244 tBu O SnPr F Cl OH NMR (oil) 245 tBu O Me F Cl OCH ₂ OCH ₂ CH ₂ OMe NMR (oil) 246 tBu OMe F Cl OH 206 -208 247 tBu OHF Cl SCH ₂ OCH ₂ CH ₂ OMe NMR (oil) 248 tBu O Cl F Cl O (2-oxo-cPn) NMR (oil) 249 tBu O Cl F Cl OCH ₂ [3- (3-Me ) Oxt] 65-70 250 tBu OMe F Cl OPrg 89-93 251 tBu O Me F Cl OCH ₂ OMe 104-108 252 tBu OHF Cl O (4-Thtp) 105-109 253 tBu O Cl F Cl SCON (Me ) ₂ 116-121 254 tBu O Cl F Cl O (3-Thp) 111-113 255 tBu O Cl F Cl O (3-Thtf) 90-91.5 256 tBu O Cl F Cl O (4-Thtp) 160-161.5 257 tBu O Cl F Cl O (5-Dxa) 115-119 258 tBu O Cl F Cl OCH ₂ (4-Dxl) 75-75.5 259 tBu O Cl F Cl O [5- (2-OEt) Thp] NMR ( Oil) 260 tBu O Cl F Cl OCH (Me) nPr NMR (O Le) 261 tBu O Cl F Cl O (2 = N-OMe) cPn 108-110 262 tBu O Cl F Cl O (2 = N-OCH 2 COOH) cPn 142-144 263 tBu O Cl F Cl O (2- oxo) cHx 150-159 264 tBu O Cl F Cl O (2 = N-OH) cPn 168-172 265 tBu O Cl F Cl O [5- (2-OMe) Thp] 98-103 266 tBu O Cl F Cl O [(3R) -3-Thf] 115 267 tBu O Cl F Cl O [3- (2-oxo-5-Me) Thf] 38 (isomer A) 268 tBu O Cl F Cl O [3- (2 -oxo-5-Me) Thf 279-281 (isomer B) 269 tBuOClFClO [3- (1-Me) Pyrd] NMR (oil) 270 tBuOClFClO [3- (2- Me) Thf] 130-134 (isomer A) 271 tBu O Cl F Cl O [3- (2-Me) Thf] 115 (isomer B) 272 tBu O Cl F Cl O [3- (2-oxo) Thf] NMR (oil) 273 tBuOClFClO (2-OMe) cHx NMR (oil) (isomer A) 274 tBuOClFClO (2-OMe) cHx NMR (oil) (isomer B) 275 tBu OHF Cl SH 107-109 276 tBu OHF Cl S (2-Me) Etn NMR (oil) 277 tBu O Cl F Cl O [(3S) -3-Thf] 115-118 278 tBu O Cl F Cl O [ 3- (4-Cl) Thf] 157.5-159 279 tBu O Cl F Cl O [4 -(3-Me) Thp] 121-122.5 (isomer A) 280 tBu O Cl F Cl O [4- (3-Me) Thp] 79-82 (isomer B) 281 tBu O Cl F Cl O [3 -(4-OMe) Thf] 103 282 tBu OFF Cl OCH ₂ OCH ₂ CH ₂ OMe NMR (oil) 283 tBu OFF Cl O (3-Thf) NMR (oil) 284 tBu O Cl F Cl O [3- (6 -Me) Thp] 120-125 (isomer A) 285 tBuOClFClO [3- (6-Me) Thp] NMR (oil) (isomer B) 286 tBuOClFClO [3- ( 4-Me) Thp] 153-159 (Isomer A) 287 tBuOClFClO [3- (4-Me) Thp] NMR (oil) (Isomer B) 288 tBuOClFClO [3- (5-Et) Thf] NMR (oil) 289 tBu O Cl F Cl O [3- (4-Me) Thf] 186-189 290 tBu O Cl F Cl OCH ₂ (2-Thf) NMR (oil) 291 tBu OHF Cl OCOOMe 292 tBu O Cl F Cl OCOOMe 293 tBu OHF Cl OCOOEt 130-135 294 tBu OCl F Cl O [3- (5-Me) Thf] 112 (isomer A) 295 tBu O Cl F Cl O [3 -(5-Me) Thf] 121 (isomer B) 296 tBu O Cl F Cl O [3- (4,4-Me ₂ ) Thf] 139-141 297 tBu O Cl F Cl O [(3S) -3 -(4,4-Me ₂ ) Th f] 138-141 298 tBu O Cl F Cl O [3- (2,5-Me ₂ ) Thf] 87-101 299 tBu O Cl F Cl O [3- (2,4-Me ₂ ) Thf] 300 tBu O Cl F Cl O [3- (2,5-Me ₂ ) Thf] 80-82 (Isomer A) 301 tBu O Cl F Cl O [3- (2,5-Me ₂ ) Thf] NMR (oil) (isomer B) 302 tBu O Cl F Cl O [3- (2,5-Me 2) Thf] 124-126 ( isomer C) 303 tBu O Cl F Cl O [3- (2,5-Me 2 ) Thf] 118-120 (Isomer D) 304 tBu O Cl F Cl O [3- (2-Me) Thp] 147-150 305 tBu O Cl F Cl O [3- (5-Me) Thp] 306 tBu O Cl F Cl O [3- (2,4-Me ₂ ) Thp] 307 tBu O Cl F Cl O [3- (2,6-Me ₂ ) Thp] 308 tBu O Cl F Cl O [3- (2 , 5-Me ₂ ) Thp] 309 tBu O Cl F Cl O [3- (4,6-Me ₂ ) Thp] 310 tBu O Cl F Cl O [3- (5,6-Me ₂ ) Thp] 311 tBu O Cl F Cl O [3- (4-Et) Thp] 312 tBu O Cl F Cl O [3- (2-Et) Thp] 313 tBu O Cl F Cl O [3- (6-Et) Thp] 314 tBu O Cl F Cl O [3- (4-OEt) Thf] 116-118 315 tBu O Cl F Cl O [3- (4-OnPr) Thf] 316 tBu O Cl F Cl O [3- (4-OiPr ) Thf] 96-98 317 tBu O Cl F Cl O [3- (4-F) Thf] 318 tBu O Cl F Cl O [3- (4,5-Me ₂ ) Thf] 319 tBu O Cl F Cl O [3- (4-Et) Thf] 320 tBu O Cl F Cl O [3- (5-F) Thp] 321 tBu O Cl F Cl O [3- (4-F) Thp] 322 tBu O Cl F Cl O [3- (4,5-F 2) Thp] 323 tBu O Cl F Cl O [3- ( 4-Cl) Thp] 324 tBu O Cl F Cl O [3- (5-Cl) Thp] 325 tBu O Cl F Cl SPrg 326 tBu OFF Cl SPrg 327 tBu O Cl FFS (3-Thf) 328 tBu O Cl F Cl S (3-Thp) 329 tBu O Cl F Cl S [3- (2-Me) Thf] 330 tBu O Cl F Cl S [3- (4-Me) Thf] 331 tBu O Cl F Cl S [3 -(2-Me) Thp] 332 tBu O Cl F Cl S [3- (4-Me) Thp] 333 tBu O SMe F Cl OCH ₂ OCH ₂ CH ₂ OMe 334 tBu O SMe F Cl OCH ₂ OMe 335 tBu O SMe F Cl OPrg 336 tBu O Cl F Cl O [4- (2-Me) Thp] 337 tBu O Cl F Cl O [4- (2,6-Me ₂ ) Thp] 338 tBu O Cl F Cl O [3 - (2-Me-4- OMe) Thf] 339 tBu O Cl F Cl O [4- (2-Me-3-OMe) Thf] 340 tBu O Cl F Cl O [3- (2,5-Me 2 -4-OMe) Thf] 341 tBu O Cl F Cl O [4- (3-OMe) Thp] 342 tBu O Cl F Cl O [3- (4-OMe) Thp] 343 tBu O Cl F Cl O [3 -(2-Me) Thf] 81-84 44 tBuOClFClO [3- (2-Et) Thf] (isomer A) 345 tBuOClFClO [3- (2-Et) Thf] (isomer B) 346 tBuOClFCl O [3- (2,5,5-Me ₃ ) Thf] 62-65 (Isomer A) 347 tBu O Cl F Cl O [3- (2,2,5-Me ₃ ) Thf] 348 tBu O Cl F Cl O [3- (2-Me-5-Et) Thf] 349 tBu O Cl F Cl O [3- (2-Et-5-Me) Thf] 350 tBu O Cl F Cl O [3- (5 , 5-Me ₂ ) Thf] 80-80.5 351 tBu O Cl Cl Cl O [3-Thf] 352 tBu O Cl Cl Cl O [3-Thp] 353 tBu O Cl Cl Cl O [4-Thp] 108-112 354 tBu O Cl Cl Cl O [3- (2-Me) Thf] 125-127.5 355 tBu O Cl Cl Cl O [3- (2,5-Me ₂ ) Thf] 154-155 (isomer A) 356 tBu O Cl Cl Cl O [3- (4-OMe) Thf] 111 357 tBu O Cl Cl Cl O [4- (2-Me) Thp] 358 tBu O Cl Cl Cl O [3- (2,5-Me ₂ ) Thf] NMR (oil) (isomer B) 359 tBu O Cl Cl Cl O [3- (5,5-Me 2) Thf] 360 tBu O Cl Cl Cl O [3-Thf [3,2-b] Thf] 361 tBu O Cl Cl Cl O [3- (6-OMe) Thf [3,2-b] Thf] 362 tBu O Cl Cl Cl O [3- (6-OEt) Thf [3,2-b] Thf] 36 tBu O Cl Cl Cl O [3- (6-OCH 2 OMe) Thf [3,2-b] Thf] 364 tBu O Cl Cl Cl O [3- (6-OCH 2 CH 2 OCH 2 CH 2 OMe) - Thf [3,2-b] Thf] 365 tBu O Cl Cl Cl O [3- (6-OCH ₂ OCH ₂ CH ₂ OMe) Thf [3,2-b] Thf] 366 tBu O Cl Cl Cl O [3 -(6-OCH ₂ CH ₂ OMe) Thf [3,2-b] Thf] 367 tBu O Cl F Cl O [3- (2,5,5-Me ₃ ) Thf] 81-82 (isomer B) 368 tBu O Cl F Cl O [ 3-Thf [3,2-b] Thf] NMR ( oil) 369 tBu O Cl F Cl O [3- (6-OSO 2 (4-Me) Ph) Thf [3, 2-b] Thf] (Isomer A) 147-150 370 tBu O Cl F Cl O [3- (6-OSO ₂ (4-Me) Ph) Thf [3,2-b] Thf] (Isomer B ) 52-53 371 tBu O Cl F Cl O [3- (6-OSO 2 Me) Thf [3,2-b] Thf] ( isomer A) NMR (oil) 372 tBu O Cl F Cl O [3- (6-OSO ₂ Me) Thf [3,2-b] Thf] (Isomer B) 55-58 373 tBu O Cl Cl Cl O [3- (6-OCHF ₂ ) Thf [3,2-b] Thf ] 374 tBu O Cl F Cl O [3- (6-OH) Thf [3,2-b] Thf] NMR ( oil) 375 tBu O Cl F Cl O [3- (6-OSi (Me) 2 tBu) Thf [3,2-b] Thf] NMR (oil) 376 tBu O Cl F Cl O [3- (6-OMe) Thf [3,2-b] Thf] (Isomer A) NMR (oil) 77 tBuOClFClO [3- (6-OMe) Thf [3,2-b] Thf] (Isomer B) NMR (oil) 378 tBuOClFClO [3- (6-OEt) Thf [3,2-b] Thf] (Isomer A) NMR (oil) 379 tBu O Cl F Cl O [3- (6-OEt) Thf [3,2-b] Thf] (Isomer B) NMR ( oil) 380 tBu O Cl F Cl O [3- (6-OCH 2 OMe) Thf [3,2-b] Thf] ( isomer A) NMR (oil) 381 tBu O Cl F Cl O [3- (6 -OCH ₂ CH ₂ OMe) Thf [3,2-b] Thf] (Isomer A) NMR (oil) 382 tBu O Cl F Cl O [3- (6-OCH ₂ OCH ₂ CH ₂ OMe) Thf [3 , 2-b] Thf] NMR (oil) 383 tBu O Cl F Cl O [3- (6-OCH ₂ OCH ₂ CH ₂ OEt) Thf [3,2-b] Thf] 384 tBu O Cl F Cl O [ 3- (6-OCHF ₂ ) Thf [3,2-b] Thf] NMR (oil) 385 tBu O Cl F Cl O [3- (6-OCH ₂ F) Thf [3,2-b] Thf] 386 tBu O Cl F Cl O [3- (6-OCF ₃ ) Thf [3,2-b] Thf] 387 tBu O Cl F Cl O [3- (4-OCH ₂ F) Thf] 388 tBu O Cl F Cl O [3- (4-OCHF ₂ ) Thf] 389 tBu O Cl F Cl O [3- (4-OCF ₃ ) Thf] 390 tBu O Cl F Cl O [3- (6-OnPr) Thf [3,2 -b] Thf] NMR (oil) 391 tBu O Cl F Cl O [3- (6-OCH ₂ CH ₂ OCH ₂ CH ₂ OMe)-Thf [3,2-b] Thf] 392 tBu O Cl F Cl O [3- (6-OCH ₂ OnPr) Thf [3,2-b] Thf] 393 tBu O Cl F Cl O [3- (6-OCH ₂ CH ₂ OiBu) Thf [3,2-b] Thf] 394 tBu O Cl F Cl O [3- (6-OCH ₂ CH ₂ OiPr) Thf [3,2 -b] Thf] 395 tBu O Cl F Cl O [3- (6-OCH ₂ CH ₂ OCH ₂ CH ₂ OiBu) Thf- [3,2-b] Thf] 396 tBu O Cl F Cl O [3- ( 6-OCH ₂ CH ₂ OCH ₂ CH ₂ OnHx) Thf- [3,2-b] Thf] 397 tBu O Cl F Cl O [3- (6-OiPr) Thf [3,2-b] Thf] 398 tBu O Cl F Cl O [3- (6-OCH ₂ OnOx) Thf [3,2-b] Thf] 399 tBu O Cl F Cl O [3- (6-OCH ₂ OMe) Thf [3,2-b] Thf] (Isomer B) NMR (oil) 400 tBu O Cl F Cl O [3- (6-OCH ₂ CH ₂ OMe) Thf [3,2-b] Thf] (Isomer B) NMR (oil) 401 tBu O Cl F Cl O [3- (4-OH) Thp] NMR (oil) 402 tBu O Cl F Cl O [3- (2,2-Me ₂ ) Thf] 403 tBu O Cl Cl Cl O [3- (2,2-Me ₂ ) Thf] 404 tBu O Cl F Cl O [3- (2,2,5,5-Me ₄ ) Thf] 405 tBu O Cl Cl Cl O [3- (2,2,5 , 5-Me ₄ ) Thf] ───────────────────────────────表 The following Table 2 shows the compound numbers and names of the compounds showing the melting points in Table 1.

[0061]

[Table 2] In Table 1, of the compound indicated as NMR in the column of physical properties,
The compound number, compound name and nuclear magnetic resonance spectrum are shown below. Note that “NMR (200 MHz, CDCl ₃ ) δ (pp
m): ”are omitted.

Compound No. 21 5-t-butyl-4-
Chloro-3- (4-chloro-5-ethoxycarbonyl
Tox-2-fluorophenyl) -4-oxazoline-
2-On 7.31 (d, 1H, J = 8.9Hz), 6.86 (d, 1H, J = 6.4Hz), 4.59 and 4.7
2 (ABq, 2H, J = 20.6Hz), 4.24 (q, 2H, J = 7.1Hz), 1.32 (s, 9
H), 1.26 (t, 3H, J = 7.1 Hz). Compound No. 25 5-t-butyl-3- [2,4-di
Fluoro-5- (2-methoxyethoxymethoxy) fe
Nil] -4-oxazolin-2-one 7.49 (t, 1H, J = 8.0 Hz), 6.97 (t, 1H, J = 10.3 Hz), 6.32 (d, 1
(H, J = 4.4Hz), 5.25 (s, 2H), 3.86 (m, 2H), 3.55 (m, 2H), 3.
35 (s, 3H), 1.23 (s, 9H). Compound No. 26 5-t-butyl-3- [2,4-di
Chloro-5- (2-methoxyethoxymethoxy) phenyl
4-Oxazolin-2-one 7.48 (s, 1H), 7.34 (s, 1H), 6.26 (s, 1H), 5.32 (s, 2H), 3.
84 (m, 2H), 3.53 (m, 2H), 3.34 (s, 2H), 1.24 (s, 9H) .Compound No. 28 5-t-butyl-4-chloro-3-
[2,4-difluoro-5- (2-methoxyethoxyme
Toxy) phenyl] -4-oxazolin-2-one 7.29 (t, 1H, J = 8.5 Hz), 7.04 (dd, 1H, J = 9.1, 10.3 Hz), 5.30
And 5.28 (ABq, 2H, J = 10.5Hz), 3.87 (m, 2H), 3.57 (m, 2H),
3.37 (s, 3H), 1.36 (s, 9H). Compound No. 35 5-t-butyl-4-chloro-3-
(4-chloro-2-fluoro-5-methylthiomethoxy
Phenyl) -4-oxazolin-2-one 7.33 (d, 1H, J = 8.9Hz), 7.01 (d, 1H, J = 6.5Hz), 5.21 (s, 2
H), 2.28 (s, 3H), 1.36 (s, 9H). Compound No. 41 5-t-butyl-3- (4-bromo
-2-fluorophenyl) -4-oxazoline-2-o
7.56 (t, 1H, J = 8.6Hz), 7.30-7.40 (m, 2H), 6.40 (d, 1H, J =
3.0Hz), 1.23 (s, 9H). Compound No. 46 5-t-butyl-3- [4-bromo
-2-fluoro-5- (2-methoxyethoxymethoxy)
C) phenyl] -4-oxazolin-2-one 7.52 (d, 1H, J = 6.9 Hz), 7.42 (d, 1H, J = 9.9 Hz), 6.39 (d, 1H,
J = 2.6Hz), 5.31 (s, 2H), 3.88 (m, 2H), 3.58 (m, 2H), 3.37
(s, 3H), 1.25 (s, 9H). Compound No. 47 5-t-butyl-4-chloro-3-
[4-Bromo-2-fluoro-5- (2-methoxyethoxy
Xymethoxy) phenyl] -4-oxazoline-2-o
7.42 (d, 1H, J = 8.7Hz), 7.19 (d, 1H, J = 6.7Hz), 5.28 and 5.2
4 (ABq, 2H, J = 10.6Hz), 3.81 (m, 2H), 3.51 (m, 2H), 3.30
(s, 3H), 1.30 (s, 9H). Compound No. 49 5-t-butyl-4-chloro-3-
[4-bromo-2-fluoro-5- (2-propynylo
Xy) phenyl] -4-oxazolin-2-one 7.51 (d, 1H, J = 5.6 Hz), 7.04 (d, 1H, J = 6.3 Hz), 4.78 (s, 2
H), 2.17 (m, 1H), 1.37 (s, 9H). Compound No. 50 5-t-butyl-3- [2-chloro
-4-fluoro-5- (2-methoxy) ethoxymethoxy
Cyphenyl] -4-oxazolin-2-one 7.33 (d, 1H, J = 8.0 Hz), 7.19 (d, 1H, J = 10.2 Hz), 6.23 (s, 1
H), 5.25 (s, 2H), 3.80 (m, 2H), 3.51 (m, 2H), 3.31 (s, 3
H), 1.20 (s, 9H). Compound No. 51 5-t-butyl-4-chloro-3-
[2-chloro-4-fluoro-5- (2-methoxyethoxy
Xymethoxy) phenyl] -4-oxazoline-2-o
7.29 (d, 1H, J = 8.0Hz), 7.24 (d, 1H, J = 10.2Hz), 5.26 and 5.2
9 (ABq, 2H, J = 9.9Hz), 3.81 (m, 2H), 3.49 (m, 2H), 3.31
(s, 3H), 1.31 (s, 9H). Compound No. 66 5-t-butyl-4-chloro-3-
[2,4-Dichloro-5- (2-ethoxyethoxy)]
Enyl] -4-oxazolin-2-one 7.52 (s, 1H), 6.98 (s, 1H), 4.17 (t, 2H, J = 4.9Hz), 3.80
(t, 2H, J = 4.9Hz), 3.59 (q, 2H, J = 7.0Hz), 1.34 (s, 9H), 1.
20 (t, 2H, J = 7.0 Hz). Compound No. 68 4-chloro-3- (4-chloro-2
-Fluorophenyl) -5- (1-ethyl-1-methyl)
Propyl) -4-oxazolin-2-one 7.25-7.38 (m, 3H), 1.80 (dq, 2H, J = 7.5,15.0Hz), 1.52 (d
q, 2H, J = 7.5,15.0Hz), 1.28 (s, 3H), 0.88 (t, 6H, J = 7.5H
z). Compound No. 71 5-t-butyl-4-chloro-3-
[4-chloro-2-fluoro-5- (4-chlorophenyl)
Ruthiomethoxy) phenyl] -4-oxazoline-2-
ON 7.47 (d, 2H, J = 8.8Hz), 7.34 (d, 1H, J = 8.8Hz), 7.30 (d, 2H,
J = 6.9Hz), 6.98 (d, 1H, J = 6.5Hz), 5.48 (s, 2H), 1.37 (s, 9
H). Compound No. 74 5-t-butyl-4-chloro-3-
(4-chloro-2-fluoro-5-phenylthiomethoxy)
(Ciphenyl) -4-oxazolin-2-one 7.50-7.58 (m, 2H), 7.28-7.39 (m, 4H), 6.97 (d, 1H, J = 6.5H
z), 1.37 (s, 9H). Compound No. 75 3- [4-Chloro-2-fluoro-
5- (2-methoxyethoxymethoxy) phenyl] -5
-(1-ethyl-1-methylpropyl) -4-oxazo
Phosphorus-2-one 7.30 (d, 1H, J = 9.9Hz), 7.28 (d, 1H, J = 6.5Hz), 5.31 and 5.3
6 (ABq, 2H, J = 8.0Hz), 3.88 (m, 2H), 3.57 (m, 2H), 3.37
(s, 3H), 1.80 (dq, 2H, J = 7.3Hz), 1.52 (dq, 2H, J = 7.3Hz),
1.28 (s, 3H), 0.89 (t, 6H, J = 7.3 Hz). Compound No. 81 5-t-butyl-4-chloro-3-
[4-chloro-2-fluoro-5- [2- (2-chloro
Ethoxy) ethoxy] phenyl] -4-oxazoline-
2-On 7.28 (d, 1H, J = 9.0Hz), 6.99 (d, 1H, J = 6.6Hz), 4.18 (t, 2H,
J = 4.6Hz), 3.90 (t, 2H, J = 4.6Hz), 3.83 (t, 2H, J = 5.8Hz),
3.62 (t, 2H, J = 5.8 Hz), 1.33 (s, 9H). Compound No. 83 5-t-butyl-4-chloro-3-
[4-chloro-2-fluoro-5- [2- (2-methoxy)
Ciethoxy) ethoxy] phenyl] -4-oxazoline
-2-on 7.31 (d, 1H, J = 9.0Hz), 6.96 (d, 1H, J = 6.5Hz), 4.20 (t, 2H,
J = 4.7Hz), 3.90 (t, 2H, J = 4.70Hz), 3.76 (t, 2H, J = 2.8Hz),
3.58 (t, 2H, J = 2.8 Hz), 3.39 (s, 3H), 1.36 (s, 9H). Compound No. 84 3- (5-benzyloxymethoxy
-4-chloro-2-fluorophenyl) -5-t-buty
Le-4-chloro-4-oxazolin-2-one 7.21-7.38 (m, 7H), 5.30-5.45 (m, 2H), 4.77 (s, 2H), 1.36
(s, 9H). Compound No. 87 5-t-butyl-4-chloro-3-
[4-chloro-2-fluoro-5- (2-vinyloxy
Ethoxy) phenyl] -4-oxazolin-2-one 7.30 (d, 1H, J = 8.0 Hz), 6.95
(D, 1H, J = 6.4 Hz), 6.51 (dd, 1
H, J = 6.8, 14.1 Hz), 4.25 (m, 2
H), 4.05 (m, 2H), 1.35 (s, 9
H). Compound No. 97 5-tert-butyl-4-chloro-3-
[4-chloro-5- (N, N-dimethylcarbamoylo)
Xy) -2-fluorophenyl] -4-oxazoline-
2-on 7.35 (d, 1H, J = 8.9 Hz), 7.34
(D, 1H, J = 6.9 Hz), 3.15 (s, 3
H), 3.03 (s, 3H), 1.36 (s, 9
H). Compound No. 98 5-t-butyl-4-chloro-3-
[4-chloro-5- (N, N-dimethylsulfamoyl)
Oxy) -2-fluorophenyl] -4-oxazoline
-2-on 7.57 (d, 1H, J = 6.7Hz), 7.39 (d, 1H, J = 9.0Hz), 3.08 (s, 6
H), 1.37 (s, 9H). Compound No. 105 5-t-butyl-4-chloro-3
-[4-Chloro-2-fluoro-5- [2- (1-methyl
Rupyrrolidin-2-yl) ethoxy] phenyl] -4-
Oxazolin-2-one 7.39 (d, 1H, J = 8.7 Hz), 6.96 (d) and 6.99 (d) (1 H, J = 6.4 Hz),
4.67 (m, 1H), 4.21 (m, 1H), 2.54 (s) and 2.56 (s) (3H), 1.
70-2.85 (m, 9H), 1.46 (s, 9H). Compound No. 128 5-t-butyl-4-chloro-3
-[4-chloro-2-fluoro-5- (2-hydroxy
Ethoxy) phenyl] -4-oxazolin-2-one 7.30 (d, 1H, J = 7.3 Hz), 6.95 (d, 1H, J = 7.0 Hz), 3.95-4.25
(m, 4H), 1.35 (s, 9H). Compound No. 133 5-t-butyl-4-chloro-3
-[4-chloro-2-fluoro-5- (2-fluoroe
Toxy) phenyl] -4-oxazolin-2-one 7.33 (d, 1H, J = 8.9 Hz), 6.94 (d, 1H, J = 6.4 Hz), 4.90 (m, 1
H), 4.68 (m, 1H), 4.35 (m, 1H), 4.20 (m, 1H), 1.36 (s, 9
H). Compound No. 177 5-tert-butyl-4-chloro-3
-[4-Chloro-5- [2- (2-ethoxyethoxy)
Ethoxy] -2-fluorophenyl] -4-oxazoly
7.29 (d, 1H, J = 9.1 Hz), 6.95
(D, 1H, J = 6.5 Hz), 4.18 (t, 2
H, J = 4.7 Hz), 3.89 (t, 2H, J =
4.4 Hz), 3.74 (dt, 2H, Jd = 1.0)
Hz, Jt = 4.4 Hz), 3.57 (m, 2H),
3.50 (t, 2H, J = 7.2 Hz), 1.35
(S, 9H), 1.24 (t, 3H, J = 7.2H
z). Compound No. 180 3- (5-bromoacetoxy-4
-Chloro-2-fluorophenyl) -5-t-butyl-
4-chloro-4-oxazolin-2-one 7.41 (d, 1H, J = 8.9 Hz), 7.29
(D, 1H, J = 6.8 Hz), 4.11 (s, 2
H), 1.36 (s, 9H). Compound No. 184 5-t-butyl-4-chloro-3
-[4-chloro-2-fluoro-5- (1,3-dioxy
Solan-2-yl) methoxyphenyl] -4-oxazo
Phosphorus-2-one 7.31 (d, 1H, J = 9.0Hz), 6.94 (d, 1H, J = 6.5Hz), 5.34 (t, 1H,
J = 3.4Hz), 3.92-4.17 (m, 6H), 1.36 (s, 9H). Compound No. 198 5-t-butyl-4-chloro-3
-[4-chloro-5- (2-ethylthioethoxy) -2
-Fluorophenyl] -4-oxazolin-2-one 7.33 (d, 1H, J = 9.0 Hz), 6.90 (d, 1H, J = 6.6 Hz), 4.19 (m, 2
H), 2.96 (t, 2H, J = 6.8Hz), 2.69 (q, 2H, J = 7.4Hz), 1.36 (s,
9H), 1.30 (t, 3H, J = 7.4 Hz). Compound No. 200 5-t-butyl-4-chloro-3
-[4-chloro-2-fluoro-5- (4-methoxyca
Rubonylbutyryloxy) phenyl] -4-oxazoly
7.38 (d, 1H, J = 8.9Hz), 7.27 (d, 1H, J = 6.8Hz), 3.74 (s, 3
H), 2.96 (t, 2H, J = 7.2Hz), 2.77 (t, 2H, J = 7.2Hz), 1.36 (s,
9H). Compound No. 201 5-t-butyl-4-chloro-3
-[4-chloro-5- [2- (1,3-dioxane-2)
-Ylethoxy)]-2-fluorophenyl] -4-o
Xazolin-2-one 7.31 (d, 1H, J = 9.0Hz), 6.90 (d, 1H, J = 6.6Hz), 4.82 (t, 1H,
J = 5.2Hz), 4.07-4.19 (m, 4H), 3.80 (td, 2H, Jt = 12.1Hz, Jd
= 2.2Hz), 2.00-2.22 (m, 3H), 1.37 (s, 9H), 1.32-1.43 (m,
1H). Compound No. 203 5-t-butyl-4-chloro-3
-[4-chloro-2-fluoro-5- (2-propoxy
Ethoxy) phenyl] -4-oxazolin-2-one 7.31 (d, 1H, J = 9.9 Hz), 6.97 (d, 1H, J = 6.5 Hz), 4.19 (t, 2H,
J = 4.8Hz), 3.82 (t, 2H, J = 4.8Hz), 3.52 (t, 2H, J = 6.7Hz),
1.61 (hexat, 2H, J = 7.4Hz), 1.37 (s, 9H), 0.93 (t, 3H, J = 7.
4Hz). Compound No. 205 5-t-butyl-4-chloro-3
-[4-chloro-2-fluoro-5- (2-isopropo
[Xyethoxy) phenyl] -4-oxazoline-2-o
7.30 (d, 1H, J = 9.0Hz), 6.97 (d, 1H, J = 6.5Hz), 4.16 (t, 2H,
J = 4.9Hz), 3.82 (t, 2H, J = 4.9Hz), 3.71 (hept, 1H, J = 6.0H
z), 1.36 (s, 9H), 1.19 (d, 6H, J = 6.0 Hz). Compound No. 206 3- [5- [2- (2-n-buto)
[Xyethoxy) ethoxy] -4-chloro-2-fluoro
Phenyl] -5-t-butyl-4-chloro-4-oxa
Zolin-2-one 7.31 (d, 1H, J = 8.9Hz), 6.95 (d, 1H, J = 6.5Hz), 4.19 (t, 2H,
J = 4.8Hz), 3.90 (t, 2H, J = 4.8Hz), 3.75 (m, 2H), 3.60 (m, 2
H), 3.47 (t, 2H, J = 6.6Hz), 1.20-1.68 (m, 4H), 1.36 (s, 9
H), 0.91 (t, 3H, J = 7.3 Hz). Compound No. 207 5-t-butyl-4-chloro-3
-[4-chloro-5- (3,3-diethoxypropoxy)
B) -2-Fluorophenyl] -4-oxazoline-2
−ON 7.31 (d, 1H, J = 9.0Hz), 6.90 (d, 1H, J = 6.5Hz), 4.80 (t, 1H,
J = 5.5Hz), 4.11 (t, 2H, J = 6.3Hz), 4.05-4.18 (m, 2H,), 3.
46-3.79 (m, 6H), 2.10-2.23 (m, 2H), 1.37 (s, 9H), 1.22 (t,
6H, J = 7.1 Hz). Compound No. 214 5-t-butyl-4-chloro-3
-[4-chloro-2-fluoro-5- (tetrahydrofuran
Lan-2-yloxy) phenyl] -4-oxazoline
-2-on 7.29 (d, 1H, J = 8.2Hz), 7.26 (d, 1H, J = 6.7Hz), 5.73 (dd, 1
H, J = 3.7,12.0Hz), 3.90-4.17 (m, 2H,), 1.90-2.35 (m, 4
H), 1.36 (s, 9H). Compound No. 215 5-t-butyl-4-chloro-3
-[4-chloro-2-fluoro-5- (2-thiophene
Carbonyloxy) phenyl] -4-oxazoline-2
−ON 8.03 (dd, 1H, J = 1.1,1.2Hz), 7.73 (dd, 1H, J = 1.2,4.9Hz),
7.39-7.45 (m, 2H,), 7.22 (dd, 1H, J = 4.9,5.0Hz), 1.36 (s,
9H). Compound No. 216 5-t-butyl-4-chloro-3
-(4-chloro-2-fluoro-5-n-propanesul
(Honyloxyphenyl) -4-oxazolin-2-one 7.52 (d, 1H, J = 6.7Hz), 7.42 (d, 1H, J = 8.9Hz), 3.33-3.41
(m, 2H), 2.07-2.14 (m, 2H), 1.37 (s, 9H), 1.15 (t, 3H, J =
7.5 Hz). Compound No. 217 5-t-butyl-4-chloro-3
-[4-Chloro-2-fluoro-5- (2-furancal
Bonyloxy) phenyl] -4-oxazoline-2-o
7.73 (d, 1H, J = 1.8Hz), 7.47 (d, 1H, J = 3.7Hz), 7.39 (d, 1H, J
J = 7.8Hz), 7.23-7.25 (m, 1H,), 6.64 (dd, 1H, J = 3.5,1.7H
z), 1.37 (s, 9H). Compound No. 219 5-t-butyl-4-chloro-3
-(4-chloro-5-diethylphosphonooxy-2-f
Fluorophenyl) -4-oxazolin-2-one 7.56 (dd, 1H, J = 1.1, 6.8Hz), 7.36 (dd, 1H, J = 1.1, 8.8Hz),
4.30 (q, 2H, J = 7.1Hz), 4.26 (q, 2H, J = 7.1Hz), 1.39 (t, 3H,
J = 7.1Hz), 1.38 (t, 3H, J = 7.1Hz), 1.36 (s, 9H). Compound No. 220 5-t-butyl-4-chloro-3
-(4-chloro-5-diethylthiophosphonooxy-2
-Fluorophenyl) -4-oxazolin-2-one 7.44 (dd, 1H, J = 1.7, 6.8 Hz), 7.36 (br.d, 1H, J = 9.1 Hz), 4.
32 (q, 2H, J = 7.1Hz), 4.27 (q, 2H, J = 7.2Hz), 1.394 (t, 3H, J
= 7.1Hz), 1.389 (t, 3H, J = 7.2Hz), 1.37 (s, 9H). Compound No. 221 5-t-butyl-4-chloro-3
-[4-chloro-5- [2- (1,3-dioxolane-
2-ylethoxy)]-2-fluorophenyl] -4-
Oxazolin-2-one 7.31 (d, 1H, J = 9.0Hz), 6.90 (d, 1H, J = 6.6Hz), 5.13 (t, 1H,
J = 4.8Hz), 4.13-4.21 (m, 2H), 3.96-4.05 (m, 2H), 3.85-
3.93 (m, 2H), 2.22 (dt, 2H, Jd = 4.8Hz, Jt = 6.5Hz), 1.37 (s,
9H). Compound No. 222 5-t-butyl-4-chloro-3
-[4-chloro-2-fluoro-5- [2- (2-hex
Siloxyethoxy) ethoxy] phenyl] -4-oxo
Sazolin-2-one 7.30 (d, 1H, J = 8.9Hz), 6.94 (d, 1H, J = 6.5Hz), 4.19 (t, 2H,
J = 5.1Hz), 3.90 (t, 2H, J = 5.1Hz), 3.76 (t, 2H, J = 5.3Hz),
3.60 (t, 2H, J = 5.3Hz), 3.46 (t, 2H, J = 6.7Hz), 1.36 (s, 9
H), 1.26-1.59 (m, 8H), 0.88 (t, 3H, J = 6.6 Hz). Compound No. 223 5-t-butyl-4-chloro-3
-[4-chloro-2-fluoro-5- [2- (2-iso
Butoxyethoxy) ethoxy] phenyl] -4-oxa
Zolin-2-one 7.30 (d, 1H, J = 9.0Hz), 6.95 (d, 1H, J = 6.5Hz), 4.19 (t, 2H,
J = 4.8Hz), 3.91 (t, 2H, J = 4.8Hz), 3.76 (t, 2H, J = 5.5Hz),
3.59 (t, 2H, J = 5.5Hz), 3.23 (d, 2H, J = 6.7Hz), 1.87 (hept,
1H, J = 6.7Hz), 1.36 (s, 9H), 0.89 (d, 6H, J = 6.7Hz). Compound No. 224 5-t-butyl-4-chloro-3
-[4-chloro-5-dimethylthiocarbamoyloxy
-2-fluorophenyl] -4-oxazoline-2-o
7.37 (d, 1H, J = 8.9Hz), 7.22 (d, 1H, J = 6.9Hz), 3.47 (s, 3
H), 3.39 (s, 3H), 1.36 (s, 9H). Compound No. 227 5-t-butyl-4-chloro-3
-[4-Chloro-2-fluoro-5- (2-methoxy-
1-methylethoxy) phenyl] -4-oxazoline-
2-one 7.29 (d, 1H, J = 9.9Hz), 7.03 (dd, 1H, J = 3.0,6.6Hz), 4.49
(br, hexat, 1H, J = 6.2Hz), 3.62 (dd, 1H, J = 6.1,10.5Hz), 3.
53 (dd, 1H, J = 4.3,10.5Hz), 3.42 (s, 3H), 1.37 (br.s, 12
H). Compound No. 228 3- [5- (3-butenyloxy)
B) -4-Chloro-2-fluorophenyl] -5-t-
Butyl-4-chloro-4-oxazolin-2-one 7.31 (d, 1H, J = 9.0 Hz), 6.88 (d, 1H, J = 6.5 Hz), 5.85-5.98
(m, 1H), 5.20 (dd, 1H, J = 1.7,15.4Hz), 5.13 (dd, 1H, J = 1.
7,11.1Hz), 4.06 (dt, 2H, Jd = 6.6Hz, Jt = 2.4Hz), 2.55-2.6
5 (m, 2H), 1.36 (s, 9H). Compound No. 229 5-t-butyl-4-chloro-3
-[4-chloro-2-fluoro-5-octyloxime
Toxyphenyl] -4-oxazolin-2-one 7.31 (d, 1H, J = 9.0 Hz), 7.21 (d, 1H, J = 6.7 Hz), 5.26 and 5.3
3 (ABq, 2H, J = 7.6Hz), 3.71 (t, 2H, J = 6.6Hz), 1.37 (s, 9H),
1.23-1.35 (m, 12H), 0.87 (t, 3H, J = 6.5 Hz). Compound No. 230 5-t-butyl-4-chloro-3
-[4-Chloro-5- (2,2-dimethoxyethoxy)
-2-fluorophenyl] -4-oxazoline-2-o
7.31 (d, 1H, J = 8.9Hz), 6.93 (d, 1H, J = 6.5Hz), 4.73 (t, 1H,
J = 5.1Hz), 4.02-4.07 (m, 2H), 3.49 (s, 3H), 3.48 (s, 3H),
1.38 (s, 9H). Compound No. 233 5-t-butyl-3- [4-chloro
2-fluorophenyl] -4-ethylthio-4-o
Xazolin-2-one 7.21-7.37 (m, 3H), 2.32 (q, 2H, J = 7.4Hz), 1.41 (s, 9H),
1.08 (t, 3H, J = 7.4 Hz). Compound No. 234 5-t-butyl-3- [4-chloro
B-2-fluoro-5- (2-methoxyethoxymethoxy)
C) phenyl] -4-ethylthio-4-oxazoline-
2-On 7.30 (d, 1H, J = 6.3Hz), 7.27 (d, 1H, J = 4.0Hz), 5.33 (s, 2
H), 3.88 (m, 2H), 3.57 (m, 2H), 3.37 (s, 3H), 2.34 (q, 2H,
J = 7.6Hz), 1.41 (s, 9H), 1.10 (t, 3H, J = 7.6Hz). Compound No. 237 5-t-butyl-3- [4-chloro
B-2-fluoro-5- (2-propynyloxy) fe
Nil] -4-ethylthio-4-oxazolin-2-one 7.32 (d, 1H, J = 8.8 Hz), 7.09 (d, 1H, J = 6.5 Hz), 4.83 (dd, 1
H, J = 2.4,13.7Hz), 4.73 (dd, 1H, J = 2.4,13.7Hz), 2.56 (t,
1H, J = 2.4Hz), 2.34 (q, 2H, J = 7.4Hz), 1.41 (s, 9H), 1.09
(t, 3H, J = 7.4Hz). Compound No. 238 5-t-butyl-3- [4-chloro
2-fluoro-2-methoxymethoxyphenyl]-
4-ethylthio-4-oxazolin-2-one 7.31 (d, 1H, J = 8.9Hz), 7.21 (d, 1H, J = 6.7Hz), 5.21,5.26
(ABq, 2H, J = 7.0Hz), 3.52 (s, 3H), 2.36 (q, 2H, J = 7.4Hz),
1.41 (s, 9H), 1.10 (s, 3H, J = 7.4Hz). Compound No. 239 3- (5-s-butoxy-4-c)
(Rolo-2-fluorophenyl) -5-t-butyl-4-
Chloro-4-oxazolin-2-one 7.30 (d, 1H, J = 9.0 Hz), 6.88 (d, 1H, J = 6.6 Hz), 4.28 (hexa
(t, 1H, J = 6.2Hz), 1.65-1.87 (m, 2H), 1.37 (s, 9H), 1.34
(d, 3H, J = 6.2Hz), 1.01 (t, 3H, J = 7.6Hz). Compound No. 241 5-t-butyl-3- [4-chloro
B-2-fluoro-5- (2-propynyloxy) fe
Nil] -4-isopropylthio-4-oxazoline-2
-ON 7.31 (d, 1H, J = 8.9Hz), 7.09 (d, 1H, J = 6.4Hz), 4.83 (dd, 1
H, J = 2.4,14.4Hz), 4.75 (dd, 1H, J = 2.4,14.4Hz), 2.66 (he
pt, 1H, J = 6.7Hz), 2.55 (t, 1H, J = 2.4Hz), 1.41 (s, 9H), 1.
09 (d, 3H, J = 6.7Hz), 1.07 (d, 3H, J = 6.7Hz). Compound No. 244 5-t-butyl-3- [4-chloro
2-fluoro-5-hydroxyphenyl] -4-p
Ropyrthio-4-oxazolin-2-one 7.18 (d, 1H, J = 9.9 Hz), 6.89 (d, 1H, J = 7.0 Hz), 6.25 (br.s,
1H), 2.25 (t, 2H, J = 7.2Hz), 1.34 (s, 9H), 1.30-1.42 (m, 2
H), 0.77 (t, 3H, J = 7.2 Hz). Compound No. 245 5-t-butyl-3- [4-chloro
B-2-fluoro-5- (2-methoxyethoxymethoxy)
C) phenyl] -4-methyl-4-oxazoline-2-
ON 7.27 (d, 1H, J = 10.1Hz), 7.23 (d, 1H, J = 7.5Hz), 5.30 (m, 2
H), 3.87 (t, 2H, J = 4.6Hz), 3.57 (m, 2H), 3.36 (s, 3H), 1.9
1 (s, 3H), 1.32 (s, 9H). Compound No. 247 5-t-butyl-3- [4-chloro
B-2-fluoro-5- (2-methoxyethoxymethyl
Thio) phenyl] -4-oxazolin-4-one 7.96 (d, 1H, J = 8.0 Hz), 7.27 (d, 1H, J = 10.3 Hz), 6.38 (d, 1
(H, J = 2.6Hz), 5.07 (s, 2H), 3.78-3.85 (m, 2H), 3.55-3.62
(m, 2H), 3.36 (s, 3H), 1.26 (s, 9H). Compound No. 248 5-t-butyl-4-chloro-3
-[4-chloro-5- (2-cyclopentanoyl) -2
-Fluorophenyl] -4-oxazolin-4-one 7.29 (d, 1H, J = 9.6 Hz), 7.16 (d, 1H, J = 6.8 Hz), 4.59 (m, 1
H), 2.34-2.57 (m, 3H), 2.10-2.30 (m, 2H), 1.84-2.04 (m,
1H), 1.37 (s, 9H). Compound No. 259 5-t-butyl-4-chloro-3
-[4-chloro-5- (2-ethoxytetrahydropyra
-5-yloxy) -2-fluorophenyl] -4-
Oxazolin-2-one 7.31 (d, 1H, J = 9.0 Hz), 6.96 (d, 1H, J = 7.6 Hz), 4.72 (m, 1
H), 4.26 (m, 1H), 3.40-3.55 (m, 2H), 3.71-3.91 (m, 2H),
1.55-2.21 (m, 4H), 1.37 (s, 9H), 1.25 (t), 1.26 (t) (3H, J
Compound number 260 5-t-butyl-4-chloro-3
-[4-Chloro-2-fluoro-5- (1-methylbutyi
Ruoxy) phenyl] -4-oxazolin-2-one 7.39 (d, 1H, J = 10.6 Hz), 6.88 (d, 1H, J = 6.6 Hz), 4.32 (m, 1
H), 1.37 (s, 9H), 1.30-1.87 (m, 4H), 0.95 (t, 3H, J = 7.0H
z). Compound No. 269 5-t-butyl-4-chloro-3
-[4-Chloro-2-fluoro-5- (1-methylpyrro
Lysin-3-yloxy) phenyl] -4-oxazoly
-2-on 7.31 (d, 1H, J = 9.0Hz), 6.80 (d, 1H, J = 6.6Hz), 4.81 (m, 1
H), 2.90-3.01 (m, 1H), 2.70-2.89 (m, 2H), 2.45-2.61 (m,
1H), 2.45 (s, 3H), 2.22-2.40 (m1H), 1.98-2.11 (m, 1H),
1.37 (s, 9H). Compound No. 272 5-t-butyl-4-chloro-3
-[4-Chloro-2-fluoro-5- (2-oxotet
Lahydrofuran-3-yloxy) phenyl] -4-o
Xazolin-2-one 7.34 (d, 1H, J = 6.3Hz), 7.33 (d, 1H, J = 9.0Hz), 4.94 (t, 1H,
J = 7.7Hz), 4.50-4.65 (m, 1H), 4.37 (dd, 1H, J = 8.6,15.7H
z), 2.60-2.88 (m, 2H), 1.36 (s, 9H). Compound No. 273 5-t-butyl-4-chloro-3
-[4-chloro-2-fluoro-5- (2-methoxy
Clohexyloxy) phenyl] -4-oxazoline-
2-one (isomer A) 7.29 (d, 1H, J = 8.2Hz), 7.03 (d) and 6.99 (d) (1H, J = 7.0Hz),
4.49 (br.s, 1H), 3.46 (br.s, 1H), 3.41 (s, 3H), 1.90-2.15
(br.s, 2H), 1.25-1.85 (m, 6H), 1.36 (s, 9H). Compound No. 274 5-t-butyl-4-chloro-3
-[4-chloro-2-fluoro-5- (2-methoxy
Clohexyloxy) phenyl] -4-oxazoline-
2-one (isomer B) 7.28 (d, 1H, J = 9.0 Hz), 7.09 (d, 1H, J = 6.7 Hz), 4.02-4.18
(m, 1H), 3.44 (s, 3H), 3.30-3.45 (m, 1H), 2.00-2.21 (m, 2
H), 1.65-1.79 (m, 2H), 1.37 (s, 9H), 1.25-1.70 (m, 4H). Compound No. 276 5-t-butyl-4-chloro-3
-[4-Chloro-2-fluoro-5- (1-propynyl)
Thio) phenyl] -4-oxazolin-2-one 8.02 (d, 1H, J = 7.9 Hz), 7.15 (d, 1H, J = 10.2 Hz), 6.38 (d, 1
H, J = 3.0 Hz), 2.08 (s, 3H), 1.20 (s, 9H) .Compound No. 282 5-t-butyl-4-fluoro-
3- [4-chloro-2-fluoro-5- (2-methoxy
Ethoxyethoxy) phenyl] -4-oxazoline-2
−ON 7.34 (d, 1H, J = 6.6Hz), 7.31 (d, 1H, J = 9.2Hz), 5.33 (s, 2
H), 3.88 (t, 2H, J = 4.6Hz), 3.57 (t, 2H, J = 4.6Hz), 3.37 (s,
3H), 1.32 (s, 9H). Compound No. 285 5-t-butyl-4-chloro-3
-[4-Chloro-2-fluoro-5- (6-methyltet
Lahydropyran-3-yloxy) phenyl] -4-o
Xazolin-2-one (Isomer B) 7.30 (d, 1H, J = 8.9 Hz), 6.96 (d, 1H, J = 6.6 Hz), 4.11-4.32
(m, 2H), 3.32-3.58 (m, 2H), 2.20-2.35 (m, 1H), 1.70-1.9
0 (m, 2H), 1.40-1.55 (m, 1H), 1.37 (s, 9H), 1.20 (d, 3H, J =
Compound No. 287 5-t-butyl-4-chloro-3
-[4-chloro-2-fluoro-5- (4-methyltet
Lahydropyran-3-yloxy) phenyl] -4-o
Xazolin-2-one (Isomer B) 7.32 (d, 1H, J = 9.0 Hz), 6.87 (d) and 6.95 (d) (1 H, J = 6.8 Hz),
4.18 (br.s, 1H), 3.92-4.14 (m, 2H), 3.40-3.58 (m, 2H),
1.93-2.07 (m, 2H), 1.45-1.57 (m, 1H), 1.36 (s, 9H), 1.14
(d, 3H, J = 6.3 Hz). Compound No. 288 5-t-butyl-4-chloro-3
-[4-Chloro-2-fluoro-5- (5-ethyltet
Lahydrofuran-3-yloxy) phenyl] -4-o
Xazolin-2-one 7.33 (d) and 7.29 (d) (1H, J = 6.3Hz), 6.91 (d) and 6.87 (d) (1H,
J = 7.0Hz), 4.91 (m, 1H), 3.94-4.15 (m, 3H), 1.61-2.10 (m,
4H), 1.36 (s, 9H), 1.00 (t) and 0.98 (t) (3H, J = 7.4 Hz). Compound No. 290 5-t-butyl-4-chloro-3
-[4-chloro-2-fluoro-5- (tetrahydrofuran
Lan-2-ylmethoxy) phenyl] -4-oxazoly
7.30 (d, 1H, J = 8.9Hz), 6.93 (d, 1H, J = 6.3Hz), 5.28 (m, 1
H), 4.30 (m, 1H), 3.72-4.08 (m, 4H), 1.70-2.17 (m, 4H),
1.35 (s, 9H). Compound No. 301 5-t-butyl-4-chloro-3
-[4-chloro-5- (2,5-dimethyltetrahydro
Furan-3-yloxy) -2-fluorophenyl]-
4-Oxazolin-2-one (isomer B) 7.32 (d, 1H, J = 9.0 Hz), 6.87 (d, 1H, J = 6.5 Hz), 4.71 (t, 1H,
J = 4.0Hz), 4.30-4.49 (m, 2H), 2.20-2.40 (m, 1H), 1.74-
1.89 (m, 1H), 1.38 (d, 3H, J = 7.6Hz), 1.36 (s, 9H), 1.28 (d,
3H, J = 6.3 Hz). Compound No. 358 5-t-butyl-4-chloro-3
-[2,4-dichloro-5- (2,5-dimethyltetra
Hydrofuran-3-yloxy) phenyl] -4-oxo
Sazolin-2-one (isomer B) 7.57 (s, 1H), 6.86 (s) and 6.84 (s) (1H), 4.31-4.51 (m, 3H),
2.56 (ddd, 1H, J = 12.1,7.4,6.5Hz), 1.67-1.78 (m, 1H), 1,37
(s, 9H), 1,34 (d, 3H, J = 7.3 Hz), 1.28 (d, 3H, J = 6.4 Hz) Compound No. 368 5-t-butyl-4-chloro-3
-[4-chloro-2-fluoro-5- (tetrahydrofuran
Rano [3,2-b] tetrahydrofuran-3-yloxo
C) phenyl] -4-oxazolin-2-one 7.32 (d, 1H, J = 9.0 Hz), 7.04 (d, J = 6.3 Hz) and 7.02 (d, 1H, J = 6.
3Hz) (1H), 4.89 (t, 1H, J = 4.2Hz), 4.72 (d, 1H, J = 1.6Hz), 4.5
5 (brs, 1H), 3.84-4.19 (m, 4H), 1.91-2.22 (m, 2H), 1,36 (s, 9
H) Compound No. 371 5-t-butyl-4-chloro-3
-[4-Chloro-2-fluoro-5- (6-mesyloxy)
Citetrahydrofurano [3,2-b] tetrahydrofura
N-3-yloxy) phenyl] -4-oxazoline-
2-one (isomer A) 7.34 (d, 1H, J = 8.9 Hz), 6.98 (d, J = 6.3 Hz) and 6.96 (d, J = 6.3 H)
z) (1H), 5.13 (q, 1H, J = 5.5Hz), 4.96 (t, 1H, J = 4.9Hz), 4.81
(brs, 1H), 4.66 (d, 1H, J = 4.4Hz), 3.89-4.28 (m, 4H), 3.15
(s, 3H), 1,37 (s, 9H) Compound No. 374 5-t-butyl-4-chloro-3
-[4-chloro-2-fluoro-5- (6-hydroxy
Tetrahydrofurano [3,2-d] tetrahydrofuran
-3-yloxy) phenyl] -4-oxazoline-2
−ON 7.34 (d, 1H, J = 8.7Hz), 6.99 (d, 1H, J = 7.0Hz), 4.81 (brs, 1
H), 4.76 (t, 1H, J = 4.9Hz), 4.61 (brs, 1H), 4.34 (q, 1H, J = 5.8
Hz), 4.26 (d, 1H, J = 10.5Hz), 4.13 (dd, 1H, J = 4.1,10.5Hz),
3.90-3.96 (m, 1H), 3.66-3.74 (m, 1H), 2.57 (brs, 1H), 1,37
(s, 9H) Compound No. 375 5-t-butyl-4-chloro-3
-[5- (6-t-butyldimethylsilyloxytetra
Hydrofurano [3,2-d] tetrahydrofuran-3-
Yloxy) -4-chloro-2-fluorophenyl]-
4-oxazolin-2-one 7.31 (d, 1H, J = 8.9 Hz), 6.96 (dd, 1H, J = 3.8, 5.0 Hz), 4.72 (br
s, 1H), 4.53-4.63 (m, 2H), 4.30 (q, 1H, J = 5.7Hz), 4.09-4.23
(m, 2H), 3.81 (dd, 1H, J = 8.8,5.8Hz), 3.62 (dd, 1H, 8.8,6.5H
z), 1.35 (s, 9H), 0.90 (s, 9H), 0.12 (s, 3H), 0.11 (s, 3H) Compound No. 376 5-t-butyl-4-chloro-3
-[4-Chloro-2-fluoro-5- (6-methoxyte
Trahydrofurano [3,2-b] tetrahydrofuran-
3-yloxy) phenyl] -4-oxazoline-2-
ON (Isomer A) 7.33 (d, 1H, J = 8.9 Hz), 6.98 (m, 1H), 4.71 to 4.85 (m, 2H), 4.6
4 (m, 1H), 4.21 (d, 2H, J = 3.4Hz), 3.91-4.01 (m, 2H), 3.63
~ 3.76 (m, 1H), 3.50 (s, 3H), 1.37 (s, 9H) Compound No.377 5-t-butyl-4-chloro-3
-[4-Chloro-2-fluoro-5- (6-methoxyte
Trahydrofurano [3,2-b] tetrahydrofuran-
3-yloxy) phenyl] -4-oxazoline-2-
ON (Isomer B) 7.32 (d, 1H, J = 8.9Hz), 7.01 (d, J = 7.2Hz) and 6.98 (d, J = 7.2H)
z) (1H), 4.68 ~ 4.80 (m, 3H), 4.05 ~ 4.15 (m, 2H), 3.83 ~
3.99 (m, 3H), 3.40 (s, 3H), 1.36 (s, 9H) Compound No. 378 5-t-butyl-4-chloro-3
-[4-chloro-5- (6-ethoxytetrahydrofura
No [3,2-b] tetrahydrofuran-3-yloxy
B) -2-Fluorophenyl] -4-oxazoline-2
-One (isomer A) 7.31 (d, 1H, J = 8.9Hz), 6.97 (brs, 1H), 4.71 ~ 4.78 (m, 2H),
4.64 (brs, 1H), 3.94 to 4.27 (m, 4H), 3.51 to 3.80 (m, 3H), 1.
35 (s, 9H), 1.25 (t, 3H, J = 7.1 Hz) Compound No. 379 5-t-butyl-4-chloro-3
-[4-chloro-5- (6-ethoxytetrahydrofura
No [3,2-b] tetrahydrofuran-3-yloxy
B) -2-Fluorophenyl] -4-oxazoline-2
-One (isomer B) 7.33 (d, 1H, J = 8.9Hz), 7.01 (d, J = 6.6Hz) and 6.98 (d, J = 6.6H)
z) (1H), 4.69-4.80 (m, 3H), 3.87-4.12 (m, 5H), 3.48-3.68
(m, 2H), 1.37 (s, 9H), 1.26 (t, 3H, J = 7.2 Hz) Compound No. 380 5-t-butyl-4-chloro-3
-[4-Chloro-2-fluoro-5- (6-methoxymeth
Toxitetrahydrofurano [3,2-b] tetrahydro
Furan-3-yloxy) phenyl] -4-oxazoly
-2-one (isomer A) 7.32 (d, 1H, J = 8.9 Hz), 6.99 (d, J = 5.4 Hz) and 6.97 (d, J = 5.4 H)
z) (1H), 4.79 (dd, 2H, J = 2.3Hz, 4.3Hz), 4.71 (d, 2H, J = 6.8H
z), 4.67 (brs, 1H), 4.27 (dd, 1H, J = 4.3Hz, 5.2Hz), 4.21 (d, 2
H, J = 3,7Hz), 4.02 (q, 1H, J = 5.4Hz), 3.69 (dd, 1H, J = 8.3Hz,
8.4 Hz), 3.42 (s, 3H), 1,36 (s, 9H) Compound No. 381 5-t-butyl-4-chloro-3
-[4-chloro-2-fluoro-5- [6- (2-meth
Xymethoxy) tetrahydrofurano [3,2-b] tet
Lahydrofuran-3-yloxy) phenyl] -4-o
Xazolin-2-one (Isomer A) 7.32 (d, 1H, J = 9.0 Hz), 6.95-7.01 (m, 1H), 4.71-4.82 (m, 2
H), 4.64 (t, 1H, J = 4.0Hz), 3.80-4.29 (m, 5H), 3.56-3.78 (m,
4H), 3.39 (s, 3H), 1,37 (s, 9H) Compound No. 382 5-t-butyl-4-chloro-3
-[4-chloro-2-fluoro-5- [6- (2-meth
(Xyethoxymethoxy) tetrahydrofurano [3,2-
b] tetrahydrofuran-3-yloxy] phenyl]
-4-oxazolin-2-one 7.33 (d, 1H, J = 8.9Hz), 6.98 (d, J = 5.4Hz) and 6.96 (d, J = 5.4H)
z) (1H), 4.85 (dd, 2H, J = 7.1Hz, 3.4Hz), 4.78 (d, 2H, J = 5.1H
z), 4.63 (brs, 1H), 4.27 (brs, 1H), 4.19 (dd, 2H, J = 2.0Hz, 1.
7Hz), 4.03 (q, 1H, J = 5.4Hz), 3.70-3.79 (m, 2H), 3.66 (d, 1H,
J = 8.4 Hz), 3.57 (t, 2H, J = 9.2 Hz), 3.40 (s, 3H), 1,36 (s, 9H) Compound No. 384 5-t-butyl-4-chloro-3
-[4-chloro-5- (6-difluoromethoxytetra
Hydrofurano [3,2-b] tetrahydrofuran-3-
Yloxy) 2-fluorophenyl] -4-oxazolyl
-2-on 7.32 (d, 1H, J = 8.9 Hz), 6.94-
6.97 (m, 1H), 6.35 (dd, 1H, J = 7
2.8, 74.4 Hz), 4.66-4.85 (m, 4
H), 4.18-4.20 (m, 2H), 4.03 (d
d, 1H, J = 7.2, 8.9 Hz), 3.77 (d
d, 1H, J = 7.5, 8.9 Hz), 1.36 (s,
9H) Compound No. 390 5-t-butyl-4-chloro-3
-[4-chloro-2-fluoro-5- (6-propoxy
Tetrahydrofurano [3,2-b] tetrahydrofuran
-3-yloxy) phenyl] -4-oxazoline-2
-ON 7.30 (d, 1H, J = 8.9 Hz), 6.94
(D, J = 6.0 Hz) and 6.97 (d, J = 6.0 Hz) (1H), 4.74 (b
rq, 2H, J = 4.4Hz), 4.61 (br.t, 1H, J = 4.2Hz), 3.91-4.25 (m,
4H), 3.58-3.72 (m, 2H), 3.36-3.47 (m, 1H), 1.62 (m, 2H), 1.3
9 (s, 9H), 0.91 (t, 3H, J = 7.4Hz) Compound No.399 5-t-butyl-4-chloro-3
-[4-Chloro-2-fluoro-5- (6-methoxymeth
Toxitetrahydrofurano [3,2-b] tetrahydro
Furan-3-yloxy) phenyl] -4-oxazoly
-2-one (isomer B) 7.32 (d, 1H, J = 8.9 Hz), 6.97 (d, J = 5.9 Hz) and 6.99 (d, J = 5.9 H)
z) (1H), 4.68-4.81 (m, 4H), 4.64 (t, 1H, J = 4.7Hz), 4.18-4.3
8 (m, 3H), 4.02 (dd, 1H, J = 6.7,8.6Hz), 3.69 (t, 1H, J = 8.4H
z), 3.42 (s, 3H), 1.36 (s, 9H) Compound No. 400 5-t-butyl-4-chloro-3
-[4-chloro-2-fluoro-5- [6- (2-meth
(Xyethoxy) tetrahydrofurano [3,2-b] tet
Lahydrofuran-3-yloxy] phenyl] -4-o
Xazolin-2-one (isomer B) 7.33 (d, 1H, J = 8.9 Hz), 7.00 (d, J = 6.6 Hz) and 6.97 (d, J = 6.6 H)
z) (1H), 4.75 (br.s, 3H), 3.85-4.11 (m, 5H), 3.60-3.75 (m, 2
H), 3.48-3.59 (m, 2H), 3.37 (s, 3H), 1.37 (s, 9H) Compound No. 401 5-t-butyl-4-chloro-3
-[4-chloro-2-fluoro-5- (4-hydroxy
Tetrahydropyran-3-yloxy) phenyl] -4
-Oxazolin-2-one 7.32 (d, 1H, J = 9.0 Hz), 6.98-7.06 (m, 1H), 4.69-4.73 (m, 1
H), 4.41-4.46 (m, 1H), 4.22-4.29 (m, 1H), 4.06-4.15 (m, 1
H), 3.96-4.02 (m, 1H), 3.76-3.85 (m, 1H), 2.40-2.54 (br.s,
1H), 1.36 (s, 9H) Of the above compounds, preferably 14, 16, 33, 4
9, 54, 55, 56, 58, 65, 73, 79, 8
1, 202, 205, 225, 239, 254, 26
6, 270, 271, 279, 280, 281, 29
8, 301, 302, 303, 343, 350, 36
8, 376, 377, 378, 379
And more preferably 16, 33, 54, 55, 58, 7
3, 225, 254, 270, 271, 281, 29
No. 8, 302, 350, 368,
Suitably, the 16th (5-t-butyl-4-chloro-3-
[4-chloro-2-fluoro-5- (2-propynylo
Xy) phenyl-4-oxazolin-2-one), 33
Number (5-t-butyl-4-chloro-3- [4-chloro-
2-fluoro-5- (1-methyl-2-propynyloxy)
Cis) phenyl] -4-oxazolin-2-one), 54
The number (5-t-butyl-4-chloro-3- (4-chloro-
2-fluoro-5-methoxyphenyl) -4-oxazo
Phosphorus-2-one), 55th (5-t-butyl-4-chloro)
B-3- [4-Chloro-2-fluoro-5- (2-meth
[Xyethoxy) phenyl] -4-oxazoline-2-o
No. 58 (5-t-butyl-4-chloro-3- (4
-Chloro-2-fluoro-5-methoxymethoxyphenyl
Ru) -4-oxazolin-2-one), No. 271 (5-
t-butyl-4-chloro-3- [4-chloro-2-fur
Oro-5- (2-methyltetrahydrofuran-3-yl
Oxy) phenyl] -4-oxazolin-2-one
(Isomer B)), No. 281 (5-t-butyl-4-chloro)
B-3- [4-Chloro-2-fluoro-5- (4-meth
Xytetrahydrofuran-3-yl) phenyl] -4-
Oxazolin-2-one), No. 350 (5-t-butyl)
-4-chloro-3- [4-chloro-2-fluoro-5-
(2,2-dimethyltetrahydrofuran-4-yloxy
C) Compound of phenyl] -4-oxazolin-2-one)
Things.

The compound represented by the general formula (I) of the present invention is produced by the following steps.

Wherein R ¹ , R ² , R ³ , R ⁴ , W, X,
Y, Z and Q have the same meanings as described above, and R ⁵ represents a chlorine atom, a lower alkoxy group, a lower haloalkoxy group, a benzoyloxy group optionally substituted by methyl, nitro, chlorine or bromine, or benzyloxy. A group, R ⁶ is a chlorine atom or a bromine atom, R ^{3 ′} is a group represented by QR ^{4 ′} , wherein Q is an oxygen atom or a sulfur atom, and R ^{4 ′} is a lower alkyl group, a cycloalkyl group , Lower alkenyl group, lower alkynyl group, acyl group, lower alkoxycarbonyl group, aryloxycarbonyl group, carbamoyl group, sulfamoyl group, lower alkylsulfonyl group, arylsulfonyl group, di (lower alkoxy) phosphoryl group, di (lower alkoxy) Thiophosphoryl, tri (lower alkyl) silyl, or the same or different selected from oxygen, sulfur and nitrogen 5 to 8 membered saturated Hajime Tamaki containing 1 to 3 heteroatoms Tsu (R 4 ^'is substituted by 1 to 3 identical or different substituents selected from the substituent group A May be.)
Is shown.

[0065]

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[0066]

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[0067]

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[0068]

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[0069]

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Hereinafter, these general production methods will be described in more detail.

(Step A) In this step, compound (II) and pinacolin derivative (III) are condensed with a base in the presence or absence of a solvent, whereby W in the general formula (I) This is a step of producing a 4-oxazolin-2-one derivative (Ic) which is an atom.

The base used in this step includes, for example, triethylamine, tributylamine, diethylisopropylamine, pyridine, 1,4-diazabicyclo [2,2,2] octane, 1,8-diazabicyclo [5,4,0 Organic tertiary amines such as undecene,
Alkali metal bases such as sodium hydride, calcium hydrogen, sodium, lithium, n-butyllithium, lithium diisopropylamide, lithium bis (trimethylsilyl) amide, sodium methoxide, t-butoxycali, sodium hydroxide, potassium hydroxide, sodium carbonate And an inorganic base such as potassium carbonate, preferably lithium bis (trimethylsilyl) amide.

The amount of the base to be used is generally 2 to 20 equivalents, preferably 2 to 10 equivalents, relative to compound (II).

The reaction is suitably carried out 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 materials to some extent. Hydrocarbons such as petroleum ether, benzene and toluene, halogenated hydrocarbons such as chloroform and methylene chloride, ethers such as ethyl ether and tetrahydrofuran, amides such as N, N-dimethylformamide and dimethyl Sulfoxides such as sulfoxide and nitriles such as acetonitrile, and mixtures of these solvents.
N-dimethylformamide.

The reaction temperature is usually from -70 to 90 ° C, preferably from 20 to 60 ° C. The reaction time varies depending mainly on the reaction temperature, the starting compound, the reaction reagent or the type of the solvent used, but is usually 15 minutes to 24 hours, preferably 15 minutes to 4 hours.

Compound (I) which is one of the starting materials in this step
I) is produced by reacting a substituted aniline with an acid chloride represented by R ⁵ COCl according to the method described in JP-A-2-42057. Also, the other starting material, pinacolin derivative (III), is
It is produced by chlorinating and brominating a pinacolin derivative according to the method described in American Chemical Society, Vol. 70, 2886 (1948).

(Step B) In this step, the compound of the present invention (I) wherein X is a hydrogen atom among the compounds represented by the general formula (I)
a) is reacted with a chlorinating agent such as chlorine gas or N-chlorosuccinimide in the presence of a solvent to give an oxazolidin-2-one which is an intermediate of the compound of the present invention and which is a raw material in Step C described below. This is a step of producing the derivative (IV) and the oxazolidine-2-one derivative (V) which is an intermediate of the compound of the present invention and is a raw material of Step F described below.

Compound (Ia), which is a starting material for this step, can be produced by Step A.

The production ratio of the compounds (IV) and (V) differs depending on the reaction conditions and the reaction substrate.

In order to mainly produce the compound (IV), that is, in order to increase the production ratio of the (IV) compared to the (V), chlorine gas is usually blown into the solution of the compound (Ia). To carry out the reaction.

The amount of chlorine gas to be used is generally 1 to 20 equivalents, preferably 2 to 10 equivalents, relative to compound (Ia).

The solvent used is not particularly limited as long as it does not hinder the reaction and dissolves the starting materials to some extent, but is preferably a halogenated hydrocarbon such as carbon tetrachloride, chloroform or methylene chloride. Kind.

The reaction is usually carried out at a temperature of 0 to 100 ° C., preferably around room temperature. The reaction time depends mainly on the reaction temperature, the starting compound, the reaction reagent, the rate of blowing chlorine gas or the type of the solvent used, but usually 1 hour.
Minutes to 3 hours, preferably 3 minutes to 30 minutes.

In order to mainly produce (V), that is, to increase the production ratio of (V) as compared with (IV), the compound (Ia) is usually reacted with N-chlorosuccinimide. The reaction is carried out by reacting chloroimides which are such mild chlorination reagents in the presence of water.

The amount of the chlorinating agent to be used is generally 1 to 20 equivalents, preferably 2 to 10 equivalents, relative to compound (Ia).

The solvent used may be water alone, but is preferably carried out in the presence of water and another solvent. The other solvent used does not inhibit the reaction and dissolves the starting material to some extent. Although there is no particular limitation as long as it does, preferably, for example, hexane, petroleum ether, benzene, hydrocarbons such as toluene, chloroform, halogenated hydrocarbons such as methylene chloride, ethyl ether, tetrahydrofuran, Ethers such as dimethoxyethane, diethylene glycol, dimethyl ether, N, N-
Amides such as dimethylformamide, dimethylsulfoxide and acetonitrile and mixtures of these solvents, more preferably dimethokiethane.

The reaction is usually carried out at -70 to 90 ° C, preferably 0 to 50 ° C. The reaction time depends mainly on the reaction temperature, the raw material compound, the type of the reaction reagent or the solvent used, but is usually 15 minutes to 24 hours,
Preferably, it is 1 to 6 hours.

(Step C) In this step, the compound (IV) produced in the step B is mixed with a dehydrochlorinating agent in the presence or absence of a solvent to give the compound of the present invention, 4-chloroform. -4-oxazolin-2-one derivative (I
This is the step of manufacturing b).

The dehydrochlorinating agents used are, for example, triethylamine, tributylamine, diethylisopropylamine, pyridine, 4-dimethylaminopyridine, 1,8
Organic amines such as -bis (dimethylamino) naphthalene, 1,4-diazabicyclo [5,4,0] octane, 1,8-diazabicyclo [5,4,0] undecene;
Alkali metal bases such as sodium hydride, calcium hydride, metallic sodium, metallic lithium, n-butyllithium, lithium diisopropylamide, lithium bis (trimethylsilyl) amide, sodium methoxide, potassium t-butoxide, sodium hydroxide, Inorganic bases such as potassium hydroxide, sodium carbonate, potassium carbonate and sodium hydrogencarbonate;
-Diazabicyclo [5,4,0] undecene, lithium bis (trimethylsilyl) amide, more preferably 1,8-diazabicyclo [5,4,0] undecene.

The amount of the dehydrochlorinating agent to be used is generally 1 to 20 equivalents, preferably 2 to 10 equivalents, relative to compound (IV).

The reaction is suitably carried out 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 materials to some extent.
Preferably, hydrocarbons such as hexane, petroleum ether, benzene, and toluene, halogenated hydrocarbons such as chloroform and methylene chloride, ethers such as ethyl ether and tetrahydrofuran, and N, N-dimethylformamide. Amides, sulfoxides such as dimethyl sulfoxide and nitriles such as acetonitrile, and mixtures of these solvents, more preferably N, N-dimethylformamide and dimethyl sulfoxide, and still more preferably dimethyl sulfoxide. It is.

The reaction temperature is usually from -70 to 90 ° C, preferably from 0 to 50 ° C. The reaction time varies depending mainly on the reaction temperature, the starting compound, the reaction reagent or the type of the solvent used, but is usually from 15 minutes to one day and preferably from 30 minutes to 6 hours.

(Step D) In this step, a compound wherein the group R ³ of the compound (Ic) is a protected hydroxyl group or thiol group,
That is, by reacting the compound (Ic ′) as R ^{3 ′} with a deprotecting agent in the presence or absence of a solvent, the compound (I) of the present invention in which R ³ is a hydroxyl group or a thiol group ( This is a step of manufacturing Id).

The deprotecting agent used may be either acidic or basic, but depends on the chemical properties of compound (Ic ').

For example, when the protecting group for a hydroxyl group or a thiol group is an ether type such as a methoxymethyl group or a methoxyethoxymethyl group, an acidic deprotecting agent may be used, or an ester type such as an acetyl group or a propionyl group may be used. In this case, a basic deprotecting agent is suitable.

Examples of acidic compounds include inorganic acids such as hydrochloric acid and sulfuric acid, Lewis acids such as titanium tetrachloride, boron trifluoride ether complex, and dichlorozinc, and organic acids such as trifluoroacetic acid and trifluoromethanesulfonic acid. And preferably trifluoroacetic acid.

Examples of the basic one include organic bases such as sodium methoxide and potassium t-butoxide, and inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate and sodium hydrogen carbonate. Yes, preferably potassium carbonate.

The amount of the deprotecting agent to be used is generally 1 to 20 equivalents, preferably 2 to 10 equivalents, relative to compound (Ic ').

The solvent used when the reaction is carried out in the presence of a solvent is not particularly limited as long as it does not inhibit the reaction and dissolves the starting material to some extent. , Hydrocarbons such as toluene, halogenated hydrocarbons such as chloroform, methylene chloride and 1,2-dichloroethane, ethers such as ethyl ether and tetrahydrofuran, N, N-
Examples include amides such as dimethylformamide, sulfoxides such as dimethylsulfoxide, nitriles such as acetonitrile, and mixtures of these solvents, and more preferably, dichloromethane and 1,2-dichloroethane.

The reaction temperature is usually from -70 to 90 ° C, preferably from 0 to 60 ° C. The reaction time varies depending mainly on the reaction temperature, the starting compound, the reaction reagent or the type of the solvent used, but is usually from 15 minutes to one day and preferably from 30 minutes to 6 hours.

(Step E) In this step, the compound (Id)
Is used as a raw material, in the presence of a solvent and in the presence of a reaction aid,
^This is a step of producing the compound (Ic ′) by reacting with the reactive derivative of No. ⁴ .

The reaction aid used in this step may be either acidic or basic, and varies depending on the chemical properties of the reactive derivative.

When the reaction assistant is basic, for example, triethylamine, tributylamine, diethylisopropylamine, pyridine, 1,4-diazabicyclo [2,
2,2] octane, 1,8-diazabicyclo [5,4,
0] organic tertiary amines such as undecene, sodium hydride, calcium hydride, sodium, lithium,
n-butyllithium, lithium diisopropylamide,
It is an alkali metal base such as lithium bis (trimethylsilyl) amide and potassium t-butoxy, and an inorganic base such as sodium hydroxide, potassium hydride, sodium carbonate and potassium carbonate, and preferably sodium hydroxide and potassium carbonate.

[0104] In this case, suitable are the reactive derivatives, for example, a halide or sulfonic acid esters of group R ^4, preferably chloro of radicals R ^4, brominated body, mesyloxy body, tosyloxy and the like And more preferably a chloro form, a mesyloxy form, or a tosyloxy form.

The amount of the reaction assistant to be used is generally 1 to 20 equivalents, preferably 2 to 10 equivalents, relative to compound (Id).

The reaction is suitably carried out 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 materials to some extent.
Preferably, hydrocarbons such as hexane, petroleum ether, benzene, and toluene, halogenated hydrocarbons such as chloroform and methylene chloride, ethers such as ethyl ether and tetrahydrofuran, and N, N-dimethylformamide. Amides, sulfoxides such as dimethyl sulfoxide, and nitriles such as acetonitrile, and mixtures of these solvents, and more preferably N, N-dimethylformamide.

The reaction temperature is usually from -70 to 150 ° C, preferably from room temperature to 120 ° C. The reaction time varies depending mainly on the reaction temperature, the starting compound, the reaction reagent or the type of the solvent used, but is usually 15 minutes to 24 hours, preferably 30 minutes to 4 hours.

When the reaction assistant is acidic, for example, inorganic bases such as hydrochloric acid and sulfuric acid, trifluoroacetic acid, acetic acid, p-toluenesulfonic acid, methanesulfonic acid, trifluoromethanesulfonic acid, pyridine p-toluenesulfonic acid An organic acid such as a salt, and preferably, p-toluenesulfonic acid and p-toluenesulfonic acid pyridine salt.

In this case, suitable as the reactive derivative are, for example, olefins in which a part of the group R ⁴ is unsaturated.

(Step F) In this step, the compound (V) produced in the step B is reacted with a fluorinating agent in the presence or absence of a solvent to obtain an intermediate of the compound of the present invention. In this step, compound (VI), which is a raw material of step G, is produced.

The fluorinating agent to be used is not particularly limited as long as it is used for converting a hydroxyl group to a fluorine atom, but dimethylaminosulfur trifluoride (DAST) is preferred.

The amount of the fluorinating agent to be used is generally 1 to 10 equivalents, preferably 1 to 4 equivalents, relative to compound (V).

The reaction is preferably carried out 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 materials to some extent. , Petroleum ethers, hydrocarbons such as benzene, chloroform, hydrogen halides such as methylene chloride, amides such as N, N-dimethylformamide, sulfoxides such as dimethyl sulfoxide, and nitriles such as acetonitrile. And a mixture of these solvents, and more preferably methylene chloride.

The reaction temperature is usually from -70 to 80 ° C, preferably from -60 to 10 ° C. The reaction time depends mainly on the reaction temperature, the raw material compound, the type of the reaction reagent or the solvent used, but is usually from 15 minutes to one day and night,
Preferably, it is 30 minutes to 2 hours.

(Step G) In this step, compound (VI) of the present invention wherein X is fluorine in formula (I) is mixed with compound (VI) produced in step F together with a dehydrochlorinating agent. 4-oxazolin-2-one (Ie)
This is the step of manufacturing.

This step can be carried out in the same manner as in step C.

(Step H) In this step, the compound (Ic) in which W is an oxygen atom in the general formula (I) is sulfurized in the presence of a thiocarbonylating reagent and a solvent to obtain a compound represented by the formula (I). Is a compound of the present invention (I
Step f).

The thiocarbonylating reagent used is, for example, phosphorus pentasulfide, 2,4-bis (4-methoxyphenyl) -1,3-dithia-2,4-diphosphetane-2,
4-disulfide and the like, preferably 2,4-bis (4
-Methoxyphenyl) -1,3-dithia-2,4-diphosphetane-2,4-disulfide.

Solvents used include, for example, aromatic hydrocarbons such as benzene, toluene and xylene, halogenated hydrocarbons such as chloroform, carbon tetrachloride, dichloroethane and tetrachloroethane, tetrahydrofuran, dioxane and dimethoxyethane. And pyridine and the like, and preferably toluene.

The reaction temperature is usually 20 to 180 ° C, preferably 50 to 120 ° C. The reaction time varies depending mainly on the reaction temperature, the starting compound, the reaction reagent or the type of the solvent used, but is usually 1 to 15 hours, preferably 4 to 15 hours.

After completion of the reaction in each of the steps A to H, the reaction target is collected from the reaction mixture by a conventional method. For example, it can be obtained by adding an organic solvent immiscible with water to a reaction mixture, washing with water, and distilling off the solvent. The obtained target compound is, if necessary, further purified by a conventional method, for example, recrystallization, reprecipitation, chromatography and the like.

The compound (I) of the present invention can be used for various weeds which are problematic in foliar treatment and soil treatment of upland crops, for example,
Buckwheat, Purslane, Chlorophycephala, Chrysanthemum, White-spotted moss, Black-spotted vine, Black-spotted horned shrimp, Ebisu-gusa, Noharagarashi, Nazuna, Ichibi, North-eastern sika deer, Field pansies, Yaegura, Seychelles convolvulus, Red-throated moss, White-nosed moss, White-nosed moss Broadleaf weeds, such as gold;
Herbicidal activity against various weeds such as blackgrass, spruce, oats, sorghum, sorghum, eelgrass, and grasshopper weeds such as grasshopper and communisaceae weeds such as communis. And no phytotoxicity which would be a problem for major crops such as corn, wheat and soybean.

The compound (I) of the present invention can be used for various weeds which are problematic in paddy fields, for example, grass weeds such as Rubiaceae; It shows herbicidal activity against cyperaceae weeds such as pine trees and sedges, and does not show any problematic phytotoxicity against rice.

Furthermore, the present invention can be used not only in fields and paddy fields, but also in orchards, mulberry fields, and non-cultivated lands.

The compound of the present invention also has an action of suppressing the growth of a plant without killing the plant. It is expected to be useful.

To prepare a herbicide and a plant growth regulator from the compound (I) of the present invention, the herbicide and the plant growth regulator are diluted with a carrier such as a solid carrier or a liquid carrier, and if necessary, are diluted with another carrier such as a surfactant. By adding a formulation auxiliary, powders, coarse powders, granules, fine granules, emulsions, suspensions, wettable powders, flowables, aqueous solvents, liquids and the like can be prepared. Of course, the purification can be stopped at any stage of the purification, and the crude product can be used as the active ingredient.

Carriers are synthetic or natural inorganic or inorganic compounds which are mixed with herbicides and plant growth regulators to aid the accessibility of the active ingredient to the plant or to facilitate storage, transport or handling of the active ingredient. Means organic material.

When used as herbicides and plant growth regulators, other fungicides, insecticides, acaricides, nematicides, herbicides, plant growth regulators, fertilizers, soil conditioners, etc. Can be applied to expand the applicable range and save labor.

As a treatment method, the preparation is usually formulated and subjected to soil treatment, foliage treatment or flooding treatment before or within about one month after emergence of the weed. Soil treatment includes soil surface treatment, soil admixture treatment, etc.Foliage treatment includes treatment from the top of the plant, as well as local treatment that treats only weeds so that they do not adhere to crops. The treatment includes spraying of granules and irrigation treatment on the water surface.

The compounds of the present invention can be used as herbicides in paddy fields, fields, orchards, pastures, lawns, forests or non-agricultural lands.

Hereinafter, the present invention will be described in more detail with reference to formulation examples and production examples, but the present invention is not limited to these.

[0132]

【Example】

[0133]

Formulation Example 1 (Wettable powder) Compound No. 16%, Emulgen 810
(Registered trademark) (surfactant manufactured by Kao Corporation) 0.5%, Demol N (registered trademark) (surfactant manufactured by Kao Corporation)
5%, 20% of Kunilite 201 (diatomaceous earth manufactured by Kunimine Industries Co., Ltd.) and 69% of Zikulite CA (clay manufactured by Zikulite Mining Co., Ltd.) were uniformly mixed and pulverized to obtain a wettable powder.

[0134]

Formulation Example 2 (Emulsion) 30% of compound No. 39, emulsifier Solpol SM10
0 (registered trademark) (Toho Chemical Co., Ltd. surfactant) 10
% And xylene 60% were mixed well to form an emulsion.

[0135]

Formulation Example 3 (Granules) 5% of compound No. 58, 2% of sodium salt of lauryl alcohol sulfate, 5% of sodium ligninsulfonate, 2% of sodium salt of carboxymethyl cellulose and 86% of clay are uniformly mixed and pulverized. I do. 20 parts by weight of water was added to 100 parts by weight of this mixture, kneaded, processed into granules of 14 to 32 mesh using an extrusion granulator, and then dried to obtain granules.

Next, the production method will be specifically described with reference to production examples.

[0137]

Example 1 5-t-butyl-3- [4-chloro-2-fluoro-5
-(2-methoxyethoxymethoxy) phenyl] -4-
Oxazolin-2-one (Compound No. 13) (Step A) Ethyl N- [4-chloro-2-fluoro-
5- (2-methoxyethoxymethoxy) phenyl] carbamate 3.59 g (11.6 mmol) and 1-bromo-3,3-dimethyl-2-butanone (2.60 g) in dimethylformamide (DMF) solution were mixed with lithium bis (trimethylsilyl). Amide (24.56 ml) (1 mol tetrahydrofuran (T
HF) solution was slowly added dropwise at room temperature. After stirring for 30 minutes, the mixture was poured into water and extracted with ethyl acetate. Dry the extract
(MgSO ₄ ) and concentrated, and the residue was purified by silica gel column chromatography to give 3.52 g (84.4%) of the desired product. 7.46 (d, 1H, J = 6.9Hz), 7.17 (d, 1H, J = 10.0Hz), 6.31 (d, 1
(H, J = 2.4Hz), 5.24 (s, 2H), 3.75-3.95 (m, 1H), 3.45-3.65
(m, 2H), 3.33 (s, 3H), 1.24 (s, 9H).

[0138]

Example 2 5-t-butyl-4-chloro-3- [2,4-dichloro-5- (2-methoxyethoxymethoxy) phenyl]-
4-oxazolin-2-one (Compound No. 27) (1)

[0139]

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(Step B) 5-Synthesized according to Example 1
t-butyl-3- [2,4-dichlorophenyl-5-
(2-Methoxyethoxymethoxy) phenyl] -4-oxazolin-2-one (Compound No. 26) (32.17 g)
Was blown with chlorine gas for 4 minutes at room temperature. After stirring the reaction solution for 10 minutes, it was poured into saturated heavy water and extracted with ethyl acetate. The extract is dried (MgSO ₄ ),
After concentration, the residue was purified by silica gel column chromatography to give 32.14 g (84.6%) of compound (IVa) and 1.0%
g (2.7%) of compound (Va) were obtained. Compound (IVa) NMR (200 MHz, CDCl ₃ ) 7.54 (s, 1H) 7.34 (s, 1H) 6.32 (s, 1H) 5.37 (s, 2H),
3.88 (m, 2H), 3.55 (m, 2H), 3.38 (s, 3H), 1.18 (s,
9H) Compound (Va) NMR (200 MHz, CDCl ₃ ) 7.54 (s, 1H) 7.30 (s, 1H), 5.65 (s, 1H), 5.36, 5.34
(ABq, 2H, J = 10.1HZ), 3.87 (m, 2H), 3.56 (m, 2
H), 3.37 (s, 3H), 1.24 (s, 9H) (2) 5-t-butyl-4-chloro-3- [2,4-dichloro-5- (2-methoxyethoxymethoxy) phenyl]-
4-oxazolin-2-one (Step C) Compound (IVa) produced by the method of (1) above
(5-t-butyl-4,5-dichloro-3- [2,4-
Dichloro-5- (2-methoxyethoxymethoxy) phenyl] -1,3-oxazolidin-2-one) (5.80
g) in dimethylsulfoxide (DMSO) solution at room temperature in 1,8-diazabicyclo [5,4,0] undec-7-
Ene (18.8 ml) was slowly added dropwise. After stirring for 30 minutes, the reaction solution was poured into water and extracted with ethyl acetate. After the extract was dried (MgSO ₄ ) and concentrated, the residue was purified by silica gel chromatography to give 2.30 g (42.6%) of the desired product. NMR (200 MHz, CDCl ₃ ) 7.56 (s, 1H), 7.30 (s, 1H), 5.38 and 5.34 (ABq, 2H, J = 7.3H
z), 3.88 (m, 2H), 3.57 (m, 2H), 3.37 (s, 3H), 1.37 (s, 9
H).

[0141]

Example 3 5-t-butyl-4-fluoro-3- [4-chloro-2
-Fluoro-5- (tetrahydrofuran-3-yloxy) phenyl] -4-oxazolin-2-one (Compound No. 283) (1)

[0142]

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(Step B) According to the method of Example 6, 5-t
-Butyl-4-chloro-3- (4-chloro-2-fluoro-5-hydroxyphenyl) -4-oxazoline-2
5-t-butyl-3- [4-chloro-5- (3-tetrahydrofuranyloxy) -2-fluorophenyl] prepared from -one and 3-tosyloxytetrahydrofuran.
N-chlorosuccinimide (7.38 g) was added to a mixed solvent of -4-oxazolin-2-one (2.82 g) in dimethoxyethane (45 ml) and water (15 ml), and the mixture was stirred at 50 ° C for 3 hours. After completion of the reaction, the reaction solution was poured into water and extracted with ethyl acetate. The extract was dried (MgSO ₄ ), concentrated and the residue was purified by silica gel column chromatography to give 1.72
g (53.1%) of 5-t-butyl-5-chloro-3- [4
-Chloro-2-fluoro-5- (tetrahydrofuranyloxy) phenyl] -4-hydroxy-1,3-oxazolidin-2-one (compound (Vb)) was obtained as crystals. 134-137 ° C (2) 5-t-butyl-5-chloro-3- [4-chloro-2-
Fluoro-5- (3-tetrahydrofuranyloxy) phenyl] -4-fluoro-1,3-oxazolidine-2
-One (Step F) Compound (Vb) produced by the method of (1) above
(5-t-butyl-5-chloro-3- [4-chloro-2
-Fluoro-5- (tetrahydrofuranyloxy) phenyl] -4-hydroxy-1,3-oxazolidine-2
-On) (1.92 g) in methylene chloride at 0 ° C. was slowly added dropwise with diethylaminosulfur trifluoride (5.85 ml). After the reaction solution was stirred at room temperature for 15 minutes, it was poured into water and extracted with methylene chloride. The extract was washed with water and saturated saline, dried (MgSO ₄ ), concentrated, and the residue was purified by silica gel column chromatography to obtain the desired product in 1.
22 g (70.5%) were obtained. NMR (200 MHz, CDCl ₃ ) 7.27 (d, 1H, J = 9.8 Hz), 6.99 (d, 1H, J = 6.7 Hz), 6.01 (d, 1H,
J = 72.5Hz), 4.91 (m, 1H), 3.85-4.06 (m, 4H), 2.12-2.26
(m, 2H), 1.20 (s, 9H). (3) 5-t-butyl-4-fluoro-3- [4-chloro-2
-Fluoro-5- (tetrahydrofuran-3-yloxy) phenyl] -4-oxazolin-2-one (Step G) 5-t-butyl-5-chloro-3- [4- produced by the method of (2) above. Chloro-2-fluoro-5-
(3-tetrahydrofuranyloxy) phenyl] -4-
Fluoro-1,3-oxazolidin-2-one (0.72
To a solution of g) in N, N-dimethylformamide (DMF), lithium bis (trimethylsilyl) amide (0.49 ml) (1M tetrahydrofuran (THF) solution) was slowly added dropwise at 0 ° C. After stirring for 1 hour at room temperature,
The reaction solution was poured into water and extracted with ethyl acetate. After the extract was dried (MgSO ₄ ) and concentrated, the residue was purified by silica gel chromatography to give 0.21 g (32%) of the desired product. NMR (200 MHz, CDCl ₃ ) 7.32 (d, 1 H, J = 8.7 Hz), 6.95 (d, 1 H, J = 6.6 Hz), 4.93 (quin
t, 1H, J = 3.6Hz), 3.89-4.10 (m, 4H), 2.18-2.27 (m, 2H),
1.32 (s, 9H).

[0144]

Example 4 5-t-butyl-4-chloro-3- [4-chloro-2-
Fluoro-5- (2-methoxyethoxymethoxy) phenyl] -4-oxazolin-2-one (Compound No. 1
4) (Step C) 5- produced according to the method of Example 2 (1)
t-butyl-4,5-dichloro-3- [4-chloro-2
-Fluoro-5- (2-methoxyethoxymethoxy) phenyl] -1,3-oxazolidin-2-one (3.33
g) in dimethylsulfoxide (DMSO) solution at room temperature in 1,8-diazabicyclo [5,4,0] undec-7-
Ene (11.2 ml) was slowly added dropwise. After stirring for 30 minutes, the reaction solution was poured into water and extracted with ethyl acetate. After the extract was dried (MgSO ₄ ) and concentrated, the residue was purified by silica gel chromatography to obtain 2.41 g (78.8%) of the desired product. NMR (200 MHz, CDCl ₃ ) 7.28 (d, 1H, J = 8.7 Hz), 7.24 (d, 1H, J = 6.5 Hz), 5.35 (m, 2
H), 3.81-3.90 (m, 2H), 3.51-3.59 (m, 2H), 3.35 (s, 3H),
1.34 (s, 9H).

[0145]

Example 5 5-t-butyl-4-chloro-3- (4-chloro-2-
(Fluoro-5-hydroxyphenyl) -4-oxazolin-2-one (Compound No. 15) (Step D) 5-t-butyl- produced by the method of Example 4
4-chloro-3- [4-chloro-2-fluoro-5-
(2-Methoxyethoxymethoxy) phenyl] -4-oxazolin-2-one (Compound No. 14) (2.19 g) in methylene chloride solution was added at room temperature to trifluoroacetic acid (3.10m).
After l) was added, the mixture was stirred at 60 ° C for 2 hours. The reaction solution was poured into saturated heavy water and extracted with ethyl acetate. The extract was dried (MgSO ₄ ) and concentrated, and the residue was purified by silica gel chromatography to give 1.55 g (90.1%) of the desired product. NMR (60 MHz, CDCl ₃ ) 7.19 (d, 1H, J = 9.0 Hz), 6.91 (d, 1H, J = 7.0 Hz), 6.36
(S, 1H), 1.37 (s, 9H)

[0146]

Example 6 5-t-butyl-4-chloro-3- [4-chloro-2-
Fluoro-5- (2-propynyloxy) phenyl-4
-Oxazolin-2-one (Compound No. 16) (Step E) 5-t-butyl- produced by the method of Example 5
4-Chloro-3- (4-chloro-2-fluoro-5-hydroxyphenyl) -4-oxazolin-2-one (Compound No. 15) (0.36 g) in dimethylformamide (D
The MF) solution was added to a suspension of sodium hydride (45 mg) (60% oil dispersion reagent) in dimethylformamide (DMF) at 0 ° C. under argon gas. After stirring for 10 minutes, propargyl bromide (118 ml) was added. 3 at room temperature
After stirring for an hour, the mixture was poured into water and extracted with ethyl acetate.
The extract was concentrated and purified by silica gel column chromatography to obtain 320 mg (80.9%) of the desired product. NMR (200 MHz, CDCl ₃ ) 7.33 (d, 1H, J = 8.9 Hz), 7.07 (d, 1H, J = 6.5 Hz), 4.8
1 (dd, 1H, J = 2.4, 15.0Hz), 4.76 (dd, 1H, J = 2.4, 15.0H
z), 2.60 (t, 1H, J = 2.4Hz), 1.37 (s, 9H)

[0147]

Example 7 5-t-butyl-4-chloro-3- (2,4-difluorophenyl) -4-oxazoline-2-thione (Compound No. 20) (Step H) According to the method of Example 4. 5-t-butyl-4-chloro-3- (2,4-difluorophenyl) -4-oxazolin-2-one produced (Compound No. 17)
(200mg) and 2,4-bis (4-methoxyphenyl)
-1,3-Dithia-2,4-diphosphetane-2,4-
Disulfide (1.82 g) in toluene for 10 hours 180
Heated at ° C. The reaction mixture was poured into water and extracted with ethyl acetate. The extract was dried (MgSO ₄ ), concentrated, and purified by silica gel column chromatography to obtain 45 mg (21.3%) of the desired product. NMR (200MHz, CDCl ₃ ) 7.38-7.49 (m, 1H), 6.98-7.11 (m, 2H), 1.42 (s, 9H)

[0148]

Example 8 5-t-butyl-4-chloro-3- [5- (1-carboxyethoxy) -4-chloro-2-fluoro] phenyl-4-oxazolin-2-one (Compound No. 34) 5-t-butyl-4-prepared according to the method of Example 4
A mixed solution of chlor-3- [4-chloro-5- (1-ethoxycarbonyl) ethoxy-2-fluoro] phenyl-4-oxazolin-2-one (Compound No. 23) (0.364 g) in water-ethanol was carbonated. Potassium (0.36 g) was added and the mixture was stirred at room temperature overnight. The pH of the reaction solution was adjusted to 3 with 10% hydrochloric acid.
After adjusting to, the mixture was poured into water and extracted with ethyl acetate. After the extract was dried (MgSO ₄ ) and concentrated, the residue was purified by silica gel column chromatography to obtain 0.285 g (84.1%) of the desired product. NMR (200 MHz, CDCl ₃ + CD ₃ OD) 7.34 (d, 1H, J = 8.9 Hz), 6.94 (br.m, 1H), 4.78 (br.m, 1
H), 1.72 (d, 3H, J = 6.8Hz) 1.26 (s, 9H)

[0149]

Example 9 5-t-butyl-4-chloro-3- (4-cyano-2-
Fluoro-5-ethoxyphenyl) -4-oxazolin-2-one (Compound No. 73) 5-t-butyl-4- produced according to the method of Example 4
Chloro-3- (4-bromo-5-ethoxy-2-fluoro) -4-oxazolin-2-one (Compound No. 12
3) (0.222 g) and copper cyanide (0.152 g) were mixed in dimethylformamide (DMF) and heated at 155 ° C. for 6 hours. The reaction solution was filtered, the filtrate was poured into water, and extracted with ethyl acetate. The extract was dried (MgSO ₄ ), concentrated, and the residue was purified by silica gel column chromatography to give 0.105.
g (55.0%) of the desired product.

NMR (200 MHz, CDCl ₃ ) 7.48 (d, 1H, J = 8.8 Hz), 6.84 (d, 1H, J = 6.8 Hz), 4.09
(Q, 2H, J = 7.0Hz) 1.48 (t, 3H, J = 7.0Hz), 1.36 (s,
9H)

[0151]

Example 10 5-t-butyl-3- (4-chloro-2-fluorophenyl) -4-oxazolin-2-one (Compound No. 1)
1) (Step A) Methyl N- (4-chloro-2-fluorophenyl) carbamate 0.203 g (1.00 mmol) and 1-bromo-3,3-dimethyl-2-butanone (0.241 g) in dimethylformamide (DMF) ) Solution, lithium bis (trimethylsilyl) amide (2.30 ml) (1M tetrahydrofuran (THF) solution) was slowly added dropwise at room temperature. After stirring for 30 minutes, the mixture was poured into water and extracted with ethyl acetate.
The extract was dried (MgSO ₄ ), concentrated, and the residue was purified by silica gel column chromatography to give 0.132 g (56.5%)
Was obtained. _{NMR (200MHz, CDCl 3) 7.10-7.80} (m, 3H), 6.37 (d, 1H, J = 3Hz), 1.27 (s, 9H).

[0152]

Example 11 5-t-butyl-3- (4-chloro-2-fluorophenyl) -4-oxazolin-2-one (Compound No. 1)
1) (Step A) 2,2,2-trichloroethyl N- (4-
Chloro-2-fluorophenyl) carbamate 0.321 g
(1.00 mmol) and 1-bromo-3,3-dimethyl-2-butanone (0.241 g) in dimethylformamide (DMF)
Add lithium bis (trimethylsilyl) amide (2.
30 ml) (1 molar tetrahydrofuran (THF) solution) was slowly added dropwise at room temperature. After stirring for 30 minutes, the mixture was poured into water and extracted with ethyl acetate. The extract was dried (MgSO ₄ ) and concentrated, and the residue was purified by silica gel column chromatography to obtain 0.238 g (88.4%) of the desired product.

[0153]

Example 12 5-t-butyl-3- (4-chloro-2-fluorophenyl) -4-oxazolin-2-one (Compound No. 1)
1) (Step A) Phenyl N- (4-chloro-2-fluorophenyl) carbamate 0.131 g (0.494 mmol) and 1-bromo-3,3-dimethyl-2-butanone (0.115 g) in dimethylformamide (DMF) ) Solution, lithium bis (trimethylsilyl) amide (1.08 ml) (1M tetrahydrofuran (THF) solution) was slowly added dropwise at room temperature. After stirring for 30 minutes, the mixture was poured into water and extracted with ethyl acetate.
The extract was dried (MgSO ₄ ), concentrated, and the residue was purified by silica gel column chromatography to give 0.065 g (48.7%)
Was obtained.

[0154]

Example 13 5-t-butyl-3- [4-chloro-2-fluoro-5
-(2-methoxyethoxymethoxy) phenyl] -4-
Oxazolin-2-one (Compound No. 13) (Step A) Ethyl N- [4-chloro-2-fluoro-
5- (2-methoxyethoxymethoxy) phenyl] carbamate (56 mg, 0.17 mmol) and 1-chloro-3,3-dimethyl-2-butanone (2.60 g) in dimethylformamide (DMF) solution were mixed with lithium bis (trimethylsilyl).
Amide (24.56 ml) (1 mol tetrahydrofuran (TH
F) solution) was slowly added dropwise at room temperature. 30 ° C for 30 minutes
Then, the mixture was poured into water and extracted with ethyl acetate. The extract was dried (MgSO ₄ ) and concentrated, and the residue was purified by silica gel column chromatography to obtain 22 mg (35%) of the desired product.

[0155]

Example 14 5-t-butyl-4-chloro-3- [4-chloro-2-
Fluoro-5- (tetrahydropyran-2-yloxy) phenyl] -4-oxazolin-2-one (Compound No. 231) (Step E) 5-t-butyl- produced by the method of Example 5
0.300 g (0.937 mmol) of 4-chloro-3- (4-chloro-2-fluoro-5-hydroxyphenyl) -4-oxazolin-2-one (Compound No. 15) and 0.342 of 3,4-dihydro-2H-pyran ml (3.75 mmol) benzene solution,
0.118 g (0.470 mmol) of p-toluenesulfonic acid pyridine salt was added, and the mixture was stirred at room temperature for 1.5 hours. After completion of the reaction, the mixture was poured into saturated heavy water and extracted with ethyl acetate. Dry the extract
(MgSO ₄ ) and concentrated, and the residue was purified by silica gel column chromatography to obtain 0.104 g (27.3%) of the desired product. NMR (200 MHz, CDCl ₃ ) 7.30 (d, 1H, J = 9.0 Hz), 7.20 (d, 1H, J = 6.8 Hz), 5.46 (br.s,
1H), 3.79-3.96 (m, 1H), 3.56-3.71 (m, 1H), 1.81-2.18 (m,
2H), 1.56-1.80 (m, 4H), 1.36 (s, 9H).

[0156]

[Reference Example 1]

[0157]

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(Step F) 5-t-butyl-5-chloro-4-hydroxy-3- (p-fluorophenyl) -oxazolidin-2 prepared according to the method of Example 3 (1)
To a solution of -one (0.5 g) in methylene chloride, diethylaminosulfur trifluoride (0.276 ml) was slowly added dropwise at 0 ° C. After stirring the reaction at room temperature for 15 minutes,
It was poured into water and extracted with methylene chloride. The extract was washed with water and saturated saline, dried (MgSO ₄ ), concentrated, and the residue was purified by silica gel column chromatography to obtain the desired compound (VI
0.30 g (60.0%) of a) was obtained.

NMR (200 MHz, CDCl ₃ ) 7.47 (dd, 2H, J = 4.6,8.8 Hz), 7.16 (t, 2H, J = 8.8H)
z), 6.17 (d, 1H, J = 68.9Hz), 1.33 (s, 9H)

[0160]

The effects of the present invention will now be specifically described with reference to biological test examples.

[0161]

[Test Example 1] Three 100 cm ² polypropylene pots (A,
B and C) were filled with paddy field soil, and seeds of dormantly awakened pups, fireflies and puppies, puppies, azaleas and kikasigusa broadleaf weeds were mixed into the A pot to 1 cm of the surface layer. Germination was carried out in the B pot, and tubers of Spodoptera litura, Krogwai, and Urikawa and growing strains of pine trees were planted. In the C pot, two-leaf stage rice seedlings were transplanted. Each pot was flooded, grown in a greenhouse, and after 3 days, treated with a predetermined amount of soil using the wettable powder prepared in Formulation Example 1 and flooded with soil. After 21 days, investigation was performed according to the following criteria. Done. Table 3 shows the results.

Judgment Criteria 0-Growth Inhibition Rate 0-10% 1-Growth Inhibition Rate 11-30% 2--Growth Inhibition Rate 31-50% 3--Growth Inhibition Rate 51-70% --- Growth inhibition rate 71-90% 5-- Growth inhibition rate 91-100% The comparative compounds in Tables 3, 4 and 5 are all the following compounds described in JP-A-62-42976. Compound.

[0163]

Embedded image

In Table 3, Table 4 and Table 5, EO is Thai millet, BL is broadleaf weed, SJ is firefly, and EA is
Is pine bye, CS is vines, EK is Krogwai, OS is paddy rice, MV is onion, SP is Urikawa, EC is Inubie, SV is Enokorogusa, DS is Mehishiba, AR is Hewyu and AT is AT Indicates strawberry, SN indicates dogwood, ZM indicates corn, TA indicates wheat, and GM indicates soybean.

[0165]

[Table 3] 化合物 Compound dose number (g / a) EO BL MV SJ EAS SP CS EK OS ──────────────────────────────────── 4 10 5 5 5 5 101500455055505004004106555544443440600545505333311100750035505200300 5 3 5 5 10 0 0 2 3 0 8 10 5 5 5 5 3 1 2 1 5 0 5 8 5 4 5 5 3 3 0 1 0 5 0 10 10 4 5 5 4 4 5 5 4 0 10 5 4 5 3 5 2 3 5 4 14 0 12 10 5 5 5 5 5 4 5 4 5 5 0 5 12 5 5 5 5 5 5 2 5 4 5 5 0 13 10 5 5 5 5 10 0 5 0 2 0 13 5 5 5 5 0 0 0 0 5 0 10 10 55 5 5 5 5 4 5 5 5 5 5 5 2 5 4 5 4 5 5 5 5 5 4 5 4 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 0 16 5 5 5 5 5 5 5 5 5 0 21 10 5 5 5 5 5 3 5 4 5 4 0 5 5 5 5 5 5 3 4 3 3 4 0 2 0 5 10 5 5 5 4 2 4 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 4 14 4 5 0 5 3 5 5 5 5 3 5 5 3 5 5 5 5 5 3 5 1 4 0 0 24 10 5 5 5 5 4 4 4 5 5 0 4 5 5 5 5 5 5 2 5 4 5 5 5 2 5 4 5 5 5 5 5 5 2 5 4 5 26 10 5 5 5 3 5 0 5 2 5 6 5 5 5 5 2 0 0 0 0 0 2 0 2 0 7 10 5 5 5 5 3 10 0 2 4 0 2 7 5 5 5 5 1 5 0 1 0 0 2 4 0 28 10 5 5 5 5 5 3 10 0 2 0 8 5 5 5 5 5 10 0 0 0 2 0 31 10 5 5 5 3 3 4 4 4 4 0 15 55 55 33 33 34 140 32 10 55 55 55 55 55 350 32 55 55 55 55 45 45 33 33 55 55 55 55 55 55 55 55 55 55 55 55 55 55 55 55 55 55 35 52 50 34 10 55 55 55 45 55 55 34 55 55 55 42 54 33 350 35 55 55 55 54 35 50 35 55 54 54 35 40 10 5 5 5 5 4 4 3 4 5 3 0 5 6 5 4 5 4 5 4 5 3 5 4 5 3 5 4 5 3 5 4 5 3 5 4 5 3 5 4 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 42 50 38 55 55 55 3 14 45 50 39 10 55 55 55 45 35 50 39 55 55 55 44 45 35 50 40 40 55 55 54 500 400 4 5 5 2 1 0 0 0 0 3 0 4 2 10 5 5 5 5 4 4 2 0 0 1 0 4 2 5 4 5 5 5 3 1 00 000 43 10 5 5 5 4 5 5 5 5 0 4 3 5 5 5 5 3 5 0 5 0 5 0 4 4 10 5 5 5 3 0 5 1 3 0 4 4 5 4 5 5 5 0 4 0 4 0 4 0 4 0 4 0 4 0 4 0 4 0 4 0 5 5 5 5 5 1 1 1 1 5 0 5 5 5 5 5 5 5 0 1 1 1 0 4 0 7 10 5 5 5 5 5 15 5 3 5 4 5 7 5 5 5 5 5 0 5 3 5 0 4 0 5 10 5 5 5 2 5 2 505 555 555 050 050 4910 555 5 545 435 549 4955 555 55 435 53 050 53 105 555 5 4 4 3 5 5 535 5 5 5 5 4 2 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 4 5 2 5 0 55 10 5 5 5 5 5 5 5 5 5 0 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 0 56 10 5 5 5 5 2 5 3 5 0 5 6 5 5 5 5 5 5 2 3 5 5 0 5 7 7 10 5 5 5 5 5 5 5 5 0 5 7 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 0 5 5 5 5 5 5 5 5 3 5 5 0 5 10 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 2 5 0 5 5 5 5 5 3 2 2 1 5 0 6 0 10 5 5 5 5 1 2 3 5 0 0 6 0 5 5 5 5 5 0 0 1 1 5 0 6 1 10 5 5 5 4 0 4 4 5 5 0 5 1 5 5 5 5 4 0 2 2 5 0 6 2 10 5 5 5 4 1 1 1 2 4 0 6 2 5 5 5 5 4 0 0 2 4 0 6 3 10 5 5 5 5 1 5 2 5 0 0 63 5 5 5 5 5 5 0 5 0 5 0 5 0 5 0 5 0 5 0 64 10 5 5 5 5 4 5 3 5 0 64 5 5 5 5 5 2 5 3 5 0 65 10 5 5 5 5 4 5 3 5 0 65 5 5 5 5 5 2 5 3 5 0 66 10 5 5 5 5 1 1 1 1 5 0 6 6 5 5 5 5 5 5 0 5 0 0 1 0 3 0 6 9 10 5 5 5 5 5 3 5 5 0 69 5 5 5 5 5 3 5 4 5 0 70 10 5 5 5 5 1 1 0 0 0 4 0 7 0 5 5 5 5 0 0 0 0 0 0 0 7 10 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 3 5 1 5 0 7 3 10 5 5 5 5 4 5 5 5 5 0 7 3 5 5 5 5 5 5 4 5 4 5 5 0 7 4 10 5 5 5 1 0 0 0 0 4 0 5 5 5 5 5 0 5 0 0 0 0 0 0 0 0 0 0 0 0 0 0 79 10 5 5 5 5 5 5 5 0 7 9 5 5 5 5 5 4 3 21 5 0 80 10 5 5 5 5 5 3 3 3 5 5 0 5 8 5 4 5 5 5 0 8 10 5 5 5 5 5 0 81 5 5 5 5 4 0 82 10 5 5 5 3 5 2 5 2 5 0 8 2 5 5 5 5 5 4 0 8 3 10 5 5 5 5 5 5 5 5 5 0 8 5 5 5 5 5 5 0 8 10 4 5 5 5 0 0 1 3 0 8 4 5 4 4 3 4 1 0 8 6 10 5 5 5 4 5 5 4 5 5 3 0 8 7 10 5 5 5 5 0 -1 5 5 5 0 7 7 5 4 5 5 5 3 0 9 4 10 5 5 5 5 5 0 5 3 5 0 9 4 5 5 5 5 3 0 95 10 10 5 5 5 5 5 0 5 2 5 0 5 5 5 5 5 5 3 0 9 7 10 5 5 5 5 5 0 1 5 5 5 0 97 5 5 5 5 5 4 0 98 10 10 5 5 5 4 0-1 5 4 5 0 9 9 5 3 5 5 5 4 0 10 3 10 5 5 5 5 5 5 5 5 0 3 0 5 5 5 5 5 5 0 5 5 5 5 5 5 5 5 5 5 2 0 5 1 5 0 5 0 5 5 4 5 5 5 0 0 107 10 5 5 5 5 4 0 5 0 5 0 7 5 5 5 5 4 0 1 1 12 10 5 5 5 5 0 5 3 5 5 0 1 12 5 3 4 4 5 2 0 116 1 10 5 5 5 5 1 5 3 5 0 0 1 16 5 3 5 5 0 0 0 1 10 10 5 5 5 5 5 5 5 5 0 117 5 4 5 5 4 0 133 10 5 5 5 5 3 5 3 5 0 133 5 5 5 5 5 0 15 2 10 5 5 5 3 5 0 1 2 2 4 4 0 5 2 5 3 5 5 5 2 0 172 10 5 5 5 5 5 5 5 5 0 17 2 5 5 5 5 5 3 5 0 5 10 5 540 000 050 173 5 4 5 5 2 0 174 10 4 5 5 3 0 2 4 4 4 0 174 5 5 4 5 5 3 0 177 10 5 5 5 5 5 5 5 5 0 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 0 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 0 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 0 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 0 5 none according to 5 4 5 5 0 5 7 5 5 5 180 10 5 5 5 5 5 5 5 5 5 5 5 5 0 5 0 5 6 5 5 5 5 5 5 5 5 5 5 5 5 5 2 5 3 5 0 181 5 5 4 5 5 3 0 183 10 5 5 5 5 4 5 4 5 3 4 5 1 5 3 4 5 3 5 5 5 5 4 5 3 4 5 1 5 3 5 5 5 5 5 5 2 0 184 10 5 5 5 5 0 -5 3 5 0 5 0 5 8 5 5 5 5 5 5 0 186 10 5 5 5 3 1 5 2 5 0 186 5 5 5 5 3 0 18 10 5 5 5 0 5 188 5 4 5 5 5 0 0 194 10 5 5 5 5 5 5 4 3 0 19 4 5 5 5 5 5 0 5 10 5 5 5 5 5 4 5 5 5 5 5 5 5 5 13 5 5 0 5 10 5 5 5 5 5 5 5 5 5 20 197 10 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 furthermore 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 also furthermore e d e s 5 5 5 4 0 200 1 10 5 5 5 5 0 5 0 5 0 5 0 5 5 5 5 4 0 0 201 10 10 5 5 5 5 0 5 3 5 0 201 5 5 5 5 4 0 202 10 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 4 5 0 5 2 5 5 5 5 5 5 0 5 0 5 10 5 5 5 4 2 5 4 5 0 5 0 5 5 5 4 5 5 2 0 205 5 10 5 5 5 4 1 5 5 5 0 5 0 5 5 4 5 5 5 2 0 206 5 5 3 0 5 5 5 0 0 20 5 4 5 5 0 0 7 0 7 10 5 5 5 4 5 1 5 1 4 0 0 7 7 5 5 5 5 5 3 0 2 0 8 10 10 4 5 5 3 0 2 0 1 0 0 20 5 5 3 3 4 0 0 0 9 9 10 5 5 5 5 3 5 2 5 0 209 5 5 5 5 3 0 210 10 10 5 5 5 4 2 5 1 5 0 2 0 5 5 5 5 5 3 3 0 0 1 1 1 1 1 0 5 5 5 2 1 2 1 4 0 0 1 1 1 5 5 5 5 5 5 0 5 0 5 10 5 10 5 5 4 2 5 1 5 0 2 1 2 5 5 5 5 4 0 2 13 10 5 5 5 4 2 5 2 4 4 0 2 13 5 5 5 5 3 0 4 10 10 5 5 5 4 2 5 2 5 0 214 5 5 5 5 5 3 5 215 10 5 5 5 5 5 5 5 5 5 5 5 5 4 5 6 5 10 5 5 5 4 5 5 5 0 5 0 5 6 5 3 5 5 2 0 217 10 5 5 5 5 0 5 5 3 5 0 5 7 5 7 5 5 5 0 219 10 5 5 5 5 5 5 5 5 0 2 1 5 5 5 5 5 3 0 220 10 3 5 5 5 3 0 2 0 4 0 220 5 2 5 5 5 10 0 221 10 5 5 5 5 5 5 3 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 3 0 222 10 5 5 5 2 0 5 1 2 0 222 5 4 5 5 1 0 223 10 5 5 5 4 1 5 1 3 0 223 5 5 5 5 2 0 224 10 5 5 5 5 1 5 2 4 0 224 5 5 5 5 3 0 225 10 5 5 5 5 3 5 3 5 5 0 5 2 5 5 5 5 5 5 5 0 2 0 6 10 5 5 5 5 4 2 5 2 5 0 2 5 6 5 5 5 5 3 0 2 2 7 10 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 2 50 0 227 5 5 5 5 4 0 230 10 5 5 5 5 5 3 5 2 5 0 230 5 5 5 5 4 4 0 231 10 5 5 5 4 3 5 1 5 0 231 5 5 5 5 3 5 3 5 3 3 0 3 2 3 1 3 1 2 3 10 5 5 3 5 2 5 0 23 2 5 5 5 5 5 0 234 10 4 5 5 5 0 2 4 4 4 0 4 3 4 5 1 4 5 0 0 0 5 3 5 5 0 5 0 0 2 0 3 0 2 3 5 5 2 3 4 0 0 0 237 10 5 5 5 3 5 240 400 37 55 45 50 500 238 10 45 55 55 23 33 50 238 53 34 45 20 39 230 55 55 42 53 150 230 39 45 54 55 240 5 5 4 1 2 1 5 0 240 5 5 5 5 3 3 0 2 3 4 3 0 3 5 5 1 1 1 1 0 4 0 4 0 4 5 3 5 1 2 4 0 0 245 10 5 5 5 5 5 2 2 5 4 0 4 5 5 5 5 5 5 5 5 0 246 10 5 5 5 4 2 2 4 5 5 0 2 4 6 5 2 5 5 1 0 247 10 5 5 5 5 4 10 0 1 1 5 0 247 5 5 4 5 3 0 248 10 5 5 5 5 5 5 5 5 3 5 4 5 0 4 0 4 0 5 5 5 5 5 0 249 1 5 5 5 5 3 5 4 5 4 0 5 0 5 5 5 5 5 4 5 0 5 0 5 0 5 5 5 5 3 5 5 5 5 0 5 0 5 5 5 5 5 5 0 5 0 5 10 5 5 5 3 5 4 5 5 5 5 4,025,10,5,5,5,4,5,5,5,5,5,5,5,5,5,5,5,5,5,3,5,5,5,5,5,3,5,5,5,5,5,5,3,5,5,5,5,3,5,5,5,5,3,5,5,5,3,5,5,5,5,3,5,5,5,3,5,5,5,3,5,5,5,3,5,5,5,5,5,3,5,5,5,5,5,5 or 5,5,5,3 or 3,025,10,5,5,5,5 I, 2,5,0,5,2,5,5,5,5,0,5,5,10,5, I / or I or V or I. 5 5 5 5 5 0 5 0 5 5 5 5 5 2 5 4 5 0 5 0 5 5 5 5 5 5 4 0 0 256 10 5 5 5 5 5 1 5 0-1 5 0 256 5 5 5 5 4 0 25 7 5 5 5 5 5 5 2 5 5 5 0 5 7 7 5 5 5 5 5 5 0 2 5 8 5 5 5 5 5 2 5 5 5 0 0 2 5 8 5 5 5 5 3 0 259 10 5 5 5 5 0 5 0 2 0 5 0 5 9 5 5 5 5 0 5 5 5 5 3 0 1 0 0 0 2 0 5 5 5 5 0 5 0 5 6 5 5 5 5 5 5 5 2 5 0 5 0 5 6 5 5 5 5 5 5 5 5 5 4 5 6 5 6 5 6 5 5 5 5 5 5 5 4 5 6 5 550 263 355 555 550 264 10 55 555 5 150 050 264 655 5 550 265 10 5 5 5 5 2 5 0 5 0 265 5 5 5 5 5 5 6 0 6 5 5 5 3 5 2 5 0 0 2 66 5 5 5 5 5 5 0 267 10 5 5 5 4 5 0 5 0 5 0 267 5 5 5 5 5 0 0 268 10 5 5 5 5 5 5 0 5 0 5 6 5 5 5 0 269 10 5 5 5 5 0 0 2 0 5 0 2 6 5 5 4 4 5 0 0 2 0 7 10 5 5 5 5 5 2 5 2 5 0 2 70 5 5 5 5 4 0 271 10 5 5 5 5 5 5 5 5 0 5 5 5 5 4 0 272 1 5 5 5 5 5 5 5 0 5 0 7 0 7 2 5 5 5 5 5 10 0 273 10 5 5 5 21 1 10 5 0 273 5 5 5 5 1 0 274 10 5 5 5 3 1 1 0 5 0 4 0 5 10 280 10 5 5 5 5 5 5 5 5 0 2 0 8 0 5 5 5 5 5 0 2 0 8 10 10 0 2 0 8 1 5 5 5 5 5 5 0 2 8 10 5 5 5 5 0 5 5 5 5 0 2 5 5 5 5 5 5 0 283 10 5 5 5 5 5 5 5 5 0 2 5 5 5 5 5 4 0 2 8 4 4 10 5 5 5 5 2 5 0 2 0 8 4 5 5 5 5 5 5 0 2 5 8 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 10 5 5 5 5 5 15 5 0 5 8 7 5 5 5 5 5 4 0 288 10 5 5 10 0 288 5 5 5 5 2 0 289 10 5 5 5 5 1 5 2 5 0 2 9 5 5 5 5 5 5 5 5 5 5 5 5 5 3 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 3 5 5 5 5 5 5 5 5 5 5 5 5 5 3 5 5 5 5 5 5 5 5 5 5 5 3 5 5 5 5 5 5 less T5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 not less than without 5 5 5 5 0 5 50 290 55 55 55 55 294 10 55 55 55 35 52 51 294 55 55 55 50 295 105 55 55 52 55 295 55 55 55 296 1055 5 5 15 15 1 296 5 5 5 5 5 0 297 10 5 5 5 5 13 0 5 0 297 5 5 5 5 4 0 298 10 5 5 5 5 2 5 2 5 0 298 5 5 5 5 5 5 0 5 0 10 5 5 5 2 0 300 5 5 5 5 5 5 0 3 0 5 10 5 5 5 5 5 1 5 1 5 0 3 0 5 1 5 5 5 5 5 0 3 2 10 10 5 5 5 5 2 5 1 5 0 3 0 5 3 5 5 5 5 5 5 5 5 5 0 5 0 5 10 5 5 5 5 2 5 2 5 0 3 0 3 5 5 5 5 5 5 0 3 0 4 10 5 5 5 5 5 2 5 1 5 0 3 0 4 5 5 5 5 5 5 0 3 14 10 5 5 5 5 5 5 2 5 5 0 3 0 5 14 5 5 5 5 0 316 1 5 5 5 5 5 5 5 0 5 0 3 1 6 5 5 5 5 5 5 0 3 4 3 5 5 5 5 5 2 5 1 5 0 5 0 5 3 5 5 5 5 4 4 4 5 0 3 0 4 10 5 5 5 5 4 4 5 2 5 0 3 0 4 3 4 55 55 40 345 10 55 55 52 43 34 45 45 55 40 34 106 55 55 55 4 50 250 350 65 55 50 350 350 5 55 52 55 250 5 5 5 4-5 0-1 353 10 5 5 4 14 14 2 4-5 1 354 10 5 5 4-5 2 4-5 2 4-5 1 354 5 5 5 3 0 355 10 5 5 4 2 1 14 0 -1 355 5 5 5 2 0 -1 356 10 5 5 4 -5 15 2 4 -5 0 356 5 5 5 4 0 358 10 5 5 1 1 1 1 0 4 -5 0 367 10 5 5 4 -5 2 3 5 5 1 367 5 5 5 4 0 -1 368 10 5 5 5 5 3 5 3 5 3 0 5 6 5 5 5 5 0 369 10 5 5 2 5 2 4-5 0 369 5 2 5 2 0 370 10 5 5 5 3 5 5 5 3 0 370 5 5 5 5 5 0 371 10 5 5 5 3 5 5 5 0 371 5 5 5 5 5 0 3 5 7 5 10 5 5 3 5 5 5 0 7 7 5 5 5 5 0 7 7 3 10 5 5 5 5 3 5 2 5 0 3 7 5 5 5 5 5 5 0} ─────────────Comparison 10 2 4 4 3 2 3 0 3 0 compounds Comparison 5 3 3 3 0 0 0 1 0 1 0 compounds ───────────────────────

[0166]

[Test Example 2] Soil treatment before the occurrence of field weeds After filling field soil in a plastic pot with an area of 150 cm ² and seeding seeds of corn, wheat, soybean, corn, wheat, and soybean, weed seeds such as dog millet, enokorogusa, meishishiba, hiyu, ichibi and dogwood. , Cover the soil to a thickness of 1cm,
It was left in the greenhouse. Immediately after the soil covering, the soil surface was treated with a predetermined dose using the wettable powder prepared in Formulation Example 1. Investigation was performed on the 21st day after the treatment according to the criteria shown in Test Example 1. Table 4 shows the results.

[0167]

[Table 4] 化合物 Compound dose number kg / ha ES SV DS AR AT SN ZM TA GM ──────────────────────────────────── 6 1 5 5 5 5 5 5 5 0.006 0.54 5 5 5 5 5 5 5 5 5 5 5 1 1 1 2 1 2 .5 5 5 5 5 5 5 5 0 0 0 14 1 5 5 5 5 5 5 5 0 0 0 0 14 0.54 5 5 5 5 5 0 5 0 5 0 1 0 0 1 5 2 5 0 0 1 0 1 5 0 5 0 5 0 5 0 5 0 5 6 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 0 5 0 0 17 1 5 5 5 5 5 5 5 5 5 5 5 0 5 0 5 2 5 5 5 5 5 5 0 5 0 5 2 5 5 5 5 5 5 5 0 0 0 0 23 1 5 5 5 5 5 5 0 0 230.5 4 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 4 5 3 5 0 0 0 3 1 1 5 5 5 5 5 5 0 1 0 31 0.55 5 5 5 5 5 5 5 0 5 5 5 5 5 5 5 5 5 0 0 0 3 1 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 0 5 / M5 ut 5am 34 1 5 5 5 5 5 5 5 0 5 1 0 3 4 5 5 5 5 5 5 5 5 5 0 0 0 1 5 5 5 5 5 5 5 0 0 0 35 0.55 5 4 5 5 5 0 0 0 3 1 5 5 5 5 5 350010370.55445550535050038152225250300380.5222140030000039150555555501003 0.5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 0 5 0 5 0 5 0 5 5 5 5 5 5 5 5 0 0 0 4 1 2 5 5 5 5 5 500 000 420.5 5 5 5 5 5 5 5 0 5 0 5 5 0 5 5 5 0 5 0 0 0 0 5 0.5 0 2 3 5 5 0 5 0 0 0 49 1 5 5 5 5 5 5 5 0 5 0 0 0 40.5 5 5 5 5 5 5 0 5 0 5 1 5 5 5 5 5 5 5 5 1 1 0 5 4 5 5 5 5 5 5 5 0 5 0 5 0 5 1 5 5 5 5 5 5 5 10 5 1 5 5 5 5 5 5 5 5 10 5 1 5 5 5 3 5 4 5 5 5 100 56 14 55 55 55 51 121 256 0.5 255 55 55 55 101 58 55 55 55 55 121 58 58 55 55 55 55 120 62 1 2 5 4 5 5 2 0 0 0 6 2 .5 0 5 2 5 3 .1 0 0 0 0 6 1 4 5 5 5 5 4 5 0 5 0 5 .1 640.5 1 4 4 4 3 4 0 0 0 0 65 1 4 5 5 5 5 5 5 5 1 1 165 0.5 3 5 4 5 5 5 5 0 5 0 6 0 6 1 2 4 5 5 5 4 0 0 0 0 6 0 6 0 5 1 4 3 1 2 3 0 0 0 0 69 1 14 5 5 5 5 5 5 6 5 6 5 6 5 6 5 6 5 6 5 6 5 5 5 10 5 6 5 5 5 5 10 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 4 5 5 5 5 also also also also be as follows: 0 730.5 3 4 5 5 3 4 0 0 0 0 7 9 1 2 5 5 5 5 5 5 0 0 1 1 7 0 5 2 1 5 5 5 1 0 0 0 0 0 1 1 3 5 5 5 4 5 5 0 0 0 0 0 0 0.50 5 5 5 5 1 4 0 0 0 1 7 1 1 2 3 4 5 5 5 0 0 0 9 7 7 5 2 3 4 5 5 5 5 0 0 0 0 10 3 1 5 5 4 5 5 5 5 2 2 0 10 3 0 5 4 5 4 4 3 5 0 10 10 116 1 2 4 4 4 2 5 1 1 1 1 1 1 1 5 1 1 3 4 4 1 4 0 0 0 1 1 1 1 1 1 1 4 4 5 4 1 5 0 0 1 1 1 1 1 1 .5 1 3 4 3 1 4 0 0 0 0 1 0 1 1 1 5 5 5 5 5 5 5 20 1 181 0.5 4 5 5 5 5 5 0 0 0 1 8 3 1 5 5 5 5 5 4 5 0 0 0 0 0 1 0 8 1 0 3 0.5 3 4 5 5 1 4 0 0 0 1 8 4 1 4 3 5 5 2 5 0 0 0 0 1 0 8 1 4 0 5 0 5 0 5 0 0 0 0 0 0 0 0 1 5 1 0 1 2 1 4 4 5 4 4 0 0 0 0 0 1 0 5 0 5 0 2 2 1 0 0 0 0 0 0 0 0 0 0 0 0 2011 1 3 5 5 4 4 5 5 0 0 0 0 0 1 0 1 0 1 0 4 4 4 5 0 0 0 0 0 5 0 1 0 5 5 5 5 4 5 0 0 0 0 205 0.5 0 2 4 5 4 5 5 0 0 0 0 210 1 2 5 5 5 5 5 5 5 0 0 0 0 1 0 0 0 0 1 3 4 2 5 0 0 0 0 2 16 1 2 4 4 4 4 4 4 0 0 0 0 2 1 6 1 5 0.5 1 3 2 1 3 0 0 0 0 2 1 5 1 4 2 4 5 5 5 5 10 0 0 0 225 0.5 4 2 4 4 3 4 0 3 0 0 2 7 1 2 3 4 3 4 5 5 0 0 0 0 2 7 2 0 0 4 0 3 0 4 0 0 0 0 2 1 2 3 4 3 3 4 3 4 1 0 0 3 0 3 2 3 0.5 3 1 1 2 0 400 0 239 1 1 1 3 4 5 2 0 0 0 0 2 0 3 0 5 0 3 4 5 5 0-0 0 0 240 1 1 1 3 4 5 5 5 5 0 0 0 0 0 2 0 5 0 0 3 4 5 0 5 0 0 0 0 0 2 0 5 1 4 2 4 4 4 5 0 0 0 1 245 0.5 3 2 3 4 4 4 5 0 0 0 0 250 1 5 5 5 5 5 5 11 1 1 250 0.54 5 5 5 5 5 5 5 0 5 0 5 1 5 5 5 5 5 5 5 5 0 5 0 3 0 5 2 5 1 5 4 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 0 5 0 257 0.5 4 1 4 5 4 5 5 0 0 0 2 5 8 1 3 5 4 5 4 5 5 0 0 1 1 258 0.5 0 0 4 4 14 0 0 0 0 260 1 3 5 5 5 2 5 0 1 0 260 0.50 3 4 504 000 290 130 355 5 550 000 0 290 0.5 1 450 550 000 ０比較 Comparison 1 2 3 3 3 3 4 0 0 0 Compound comparison 0.5 0 1 1 1 1 1 2 0 0 Compound ────────────────────────────────────

[0168]

[Test Example 3] Field weed growth stage foliage treatment Fill a field soil into a plastic pot with an area of 150 cm ² and sow seeds of weed, corn, wheat and soybean of rice millet, enokorogusa, mehisiba, hiyuzu, ichibi, and dogwood. After that, the soil was covered to a thickness of 1 cm. Thereafter, the cells were grown in a greenhouse, and two weeks later, Preparation Example 1
Using the wettable powder prepared in the above, a predetermined amount was prepared and sprayed on the foliage of the plant. On the 14th day after the treatment, a survey was conducted according to the criteria shown in Test Example 1. Table 5 shows the results.

[0169]

[Table 5] 化合物 Compound concentration number (ppm) ES SV DSAR AT SN ZM TA GM １２ 12 125 4 5 4 5 5 5 1 0 2 14 125 4 4 4 5 5 5 5 1 1 2 15 125 3 3 3 5 5 5 5 0 0 1 1 1 1 2 1 2 5 1 5 5 5 5 5 5 2 1 3 2 1 2 1 2 1 3 5 3 5 5 5 5 0 0 2 2 3 1 3 1 3 5 15 55 00 00 24 125 4 14 45 55 50 121 22 27 125 23 33 55 55 00 01 28 125 22 22 55 55 00 00 29 25 12 22 25 54 00 0 30 125 2 2 5 5 5 5 5 0 0 0 1 1 1 3 2 3 2 3 5 3 5 5 5 5 1 1 1 2 3 3 3 3 5 3 3 3 5 5 5 2 0 2 3 4 1 4 5 4 5 5 35 55 50 1 135 125 24 44 55 55 50 23 36 36 22 22 55 55 100 37 125 25 32 55 55 00 00 38 125 23 33 55 55 00 0 39 125 2 3 3 5 5 5 5 5 0 0 0 0 0 0 0 0 0 0 1 2 0 5 2 5 5 5 5 0 0 2 4 2 1 2 1 2 2 2 2 5 5 5 5 10 11 0 43 125 2 2 2 5 5 5 5 5 0 0 0 4 4 1 2 2 2 2 3,550,045,45,125,1,2,2,5,5,500,2,47,125 1,2,5,5,5,500,1, 48,125 1,3,5,5,5,5,0,5,5,5,5,5,5,5,5,5,5,5,5,5,5,5,5,5,5,5,5,5,5,5,5,4,1,5 51 125 1 2 2 3 2 5 5 0 5 0 5 1 3 1 2 2 5 5 5 5 5 0 0 2 5 4 5 4 5 5 5 5 5 5 5 1 1 4 4 5 5 5 5 3 3 4 3 5 5 5 1 1 1 4 5 5 5 5 3 3 3 3 5 5 5 5 11 3 57 125 2 2 3 5 5 5 0 5 3 5 5 5 5 5 5 5 5 5 5 5 1 1 4 1 5 1 5 1 1 5 1 2 1 2 5 5 50,000 260 125 2 222 55 55 500 360 61 125 222 2 55 50 102 62 125 22 15 55 50 00 63 125 21 21 55 50 00 64 125 2 2 3 5 5 5 0 1 2 65 125 3 4 4 4 5 5 5 10 3 0 3 6 6 6 5 12 1 5 2 5 5 5 0 0 2 69 2 125 5 2 4 4 4 5 5 1 1 2 70 1 2 5 2 3 1 3 4 5 0 1 0 72 125 3 4 3 5 5 5 5 10 7 7 1 5 1 4 7 4 5 5 5 1 1 1 2 7 4 5 1 4 7 4 5 5 5 5 1 1 2 79 125 4 5 4 5 5 5 5 2 1 2 80 125 3 4 4 5 5 5 1 1 0 1 1 1 1 2 1 2 2 1 2 1 2 1 2 1 4 4 4 3 5 5 0 5 1 1 2 83 125 3 3 4 3 5 5 5 0 5 2 0 1 2 1 2 1 2 3 4 5 5 5 5 10 0 1 1 86 125 2 4 4 5 5 5 10 0 2 87 125 2 3 3 5 5 5 5 0 5 0 7 3 7 7 1 2 3 3 4 4 5 5 1 1 2 ... 5 3 3 3 5 5 5 5 5 1 0 1 1 1 3 1 3 1 3 5 3 5 5 1 0 1 1 2 1 1 1 1 1 1 1 1 2 1 2 1 2 1 2 1 1 1 1 1 2 1 3 1 2 3 4 4 5 5 5 5 5 0 5 0 0 2 152 2 125 4 4 5 5 5 0 0 1 173 125 3 4 3 5 5 5 5 11 1 1 1 1 4 1 5 1 3 1 3 3 3 5 5 5 5 0 0 1 1 1 7 1 5 1 3 1 3 3 5 5 5 5 1 1 2 180 125 3 4 4 5 5 5 5 1 1 1 1 1 1 1 1 5 1 5 5 5 5 5 5 11 1 3 183 125 4 4 4 4 5 5 5 11 1 3 184 125 4 4 4 5 5 5 11 12 185 125 4 4 4 5 5 5 10 0 1 186 125 3 4 4 5 5 5 0 5 0 0 0 188 125 3 4 5 5 5 5 5 5 0 5 2 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 6 5 6 5 6 5 6 5 6 5 6 5 6 5 5 5 5 5 5 0 5 2 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 6 5 6 5 6 5 6 5 6 5 6 5 6 5 6 5 6 5 6 5 6 5 6 5 5 5 5 5 5 0 5 2 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 6 5 6 5 6 5 6 5 6 5 6 5 6 5 6 5 5 5 5 5 5 5 5 5 5 5 5 0 5 2 5 5 5 5 5 5 450 000 197 125 2 3 2 4 4 4 5 0 0 0 198 125 3 4 555002 200 125 33 33 34 51 111 22 201 125 3 22 55 51 113 202 125 22 21 55 50 121 203 125 43 33 55 52 113 205 125 34 4 5 5 1 1 2 1 2 1 2 1 0 1 2 1 3 1 3 1 3 1 2 1 3 1 2 1 3 1 2 1 3 1 2 1 3 1 2 1 3 1 2 5 5 5 5 1 2 3 2 1 1 1 1 1 2 1 2 1 5 1 5 3 4 4 4 5 0 1 1 219 125 4 4 4 4 5 5 0 1 2 2 2 3 1 2 3 5 3 4 3 4 5 0 1 1 225 125 2 3 1 5 5 1 1 2 239 125 4 2 4 5 5 2 1 2 248 125 345055101252251125344445550112525412533332530510222512533333455511222601253333351121266266125 3 2 3 5 5 1 1 4 270 125 3 2 3 5 5 5 1 1 3 273 125 2 2 5 5 1 1 2 277 125 2 2 2 5 5 1 1 4 278 125 2 2 2 5 5 10 2 279 125 2 2 3 3 5 5 1 1 3 282 125 3 2 2 5 5 5 0 1 1 283 125 4 3 3 5 5 1 1 2 290 125 2 3 3 3 5 5 5 5 0 0 1 1 1 3 1 3 4 3 1 5 3 5 2 5 5 5 10 0 ─────────────────Comparative 125 1 2 1 3 4 4 0 0 0 Compound ───────────────────── ───────────────

──────────────────────────────────────────────────続 き Continuing on the front page (72) Inventor Takeshi Endo 1041 Yasu-cho, Yasu-cho, Yasu-gun, Shiga Prefecture Sankyo Co., Ltd. (72) Inventor Masahiro Shindo 1041 Yasu-cho, Yasu-cho, Yasu-gun, Shiga Prefecture Sankyo Co., Ltd. (56) References JP, A 62-42976 (JP, A) (58) Fields investigated (Int. Cl. ⁷ , DB name) C07D 263/38 C07D 263/46 C07D 413/12 CA (STN) CAOLD (STN) REGISTRY (STN )

Claims (2)

(57) [Claims] 1. A compound of the general formula (I) [Wherein, R ¹ is a methyl group, R ² is a methyl group, X is a hydrogen atom, a halogen atom, a lower alkyl group or a lower alkylthio group, and Y and Z are the same or different and are a hydrogen atom, a halogen atom, a lower alkyl group. Or a cyano group, W is an oxygen atom or a sulfur atom, R ³ is a hydrogen atom, a lower alkyl group or a group represented by the formula —QR ⁴ , wherein Q is an oxygen atom or a sulfur atom, and R ⁴ is hydrogen. Atom, lower alkyl group, cycloalkyl group, lower alkenyl group, lower alkynyl group, acyl group, lower alkoxycarbonyl group, aryloxycarbonyl group, carbamoyl group, sulfamoyl group, lower alkylsulfonyl group, arylsulfonyl group, di (lower alkoxy A) a phosphoryl group, a di (lower alkoxy) thiophosphoryl group, a tri (lower alkyl) silyl group or an oxygen atom, a sulfur atom and 5 to 8 containing the same or different 1 to 3 heteroatoms selected from nitrogen atoms
A membered saturated heterocyclic group (R ⁴ may be substituted with 1 to 3 identical or different substituent (s) selected from Substituent Group A shown below (Substituent Group A) halogen atom, lower alkyl group , Cycloalkyl group, hydroxyl group, oxo group, aryl group, aryloxy group, lower alkylthio group, arylthio group, acyl group, acylamino group, acyloxy group, lower alkoxycarbonyl group, cyano group, hydroxyimino group, oxygen atom and nitrogen atom And a 4- to 6-membered saturated heterocyclic group containing 1 to 3 hetero atoms which are the same or different and a lower alkoxy group which may be substituted by halogen, nitro, lower alkoxy or carboxy lower alkyl, tri ( Lower alkyl) silyloxy group, lower alkylsulfonyloxy group, arylsulfonyloxy group Shows a shows a group.)}. An oxazoline derivative represented by the formula: 2. A herbicidal composition comprising the compound of claim 1 as an active ingredient.