JPH10287654A - Pyrazolone derivative, and herbicide - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a new pyrazolone derivative useful as a herbicide for fields and non-arable lands, having a high herbicidal effect against a variety of field weeds at low dosages in either case of soil and foliage treatments. SOLUTION: This compound is a new pyrazolone derivative shown by formula I [R is H, (substituted) phenyl, (substituted) furyl, (substituted) thienyl, etc.; X is cyano, nitro, (1-4C alkoxy)carbonyl, etc.; Y is H, a 1-6C alkyl, 3-6C cycloalkyl, 1-6C haloalkyl, etc.; Z is O or S; L is a single bond, (substituted) 1-6C alkylene, (substituted) 2-6C alkenylene, etc.; (n) is 0 or 1; when A is a single bond, B is NR<2> , etc., (R<2> is H, methyl, etc.)], e.g. 3-cyano-1-methyl-4-[1-(4- trifluoromethylbenzylamino)ethylidene]pyrazolin-5-one. This compound is obtained, e.g. by reacting an intermediate of formula III formed from an oxaloacetic diester of formula II as starting material with a carbonyl chloride, followed by reacting the resultant compound of formula IV with an amine.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

The present invention relates to a novel pyrazolone derivative and a pesticide containing the derivative as an active ingredient.
In particular, it relates to herbicides.

[0002]

BACKGROUND OF THE INVENTION With respect to pyrazolone derivatives,
Patent application No. 316138 and DE4130833 describe a herbicide, and DE3728278 describes a herbicide and a fungicide.

[0003]

Means for Solving the Problems As a result of intensive studies on novel pyrazolone derivatives, the present inventors have found that the compound of the present invention represented by the following formula has an excellent herbicidal action, and to complete the present invention. Reached. That is, the present invention provides a compound of the formula (I):

[0004]

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[Wherein, R is a hydrogen atom, a phenyl group optionally substituted with Qa, a pyridyl group optionally substituted with Qa, a furyl group optionally substituted with Qa, and a substituent substituted with Qa. Optionally substituted with a thienyl group, a naphthyl group optionally substituted with Qa or an optionally substituted Qa
Represents 1,2-oxymethylene phenyl group, Qa is halogen atom, C ₁ -C ₄ alkyl group, a phenyl group, C ₁ -C ₄
An alkoxy group, a phenoxy group, a C ₁ -C ₄ haloalkyl group, a C ₁ -C ₄ haloalkoxy group, a C ₁ -C ₄ alkylthio group, a phenylthio group, a C ₁ -C ₄ alkylsulfonyl group,
C ₁ -C ₄ haloalkylthio group, C ₁ -C ₄ alkylamino group, di (C ₁ -C ₄ alkyl) amino group, C ₁ -C ₄ alkoxycarbonyl group, a phenoxycarbonyl group, amide groups, C ₁ -C ₄ alkylamide group, phenylamide group, di (C ₁ -C ₄ alkyl) amide group, nitro group, cyano group,
Represents one or more substituents selected from a hydroxy group, an acetyloxy group and a benzoyloxy group, wherein R ¹ is C ₁ -C
₆ alkyl group, C ₃ -C ₆ cycloalkyl group, C ₁ -C ₆ haloalkyl group, C ₁ -C ₆ alkoxy group, C ₁ -C ₆ alkylamino group, C ₁ -C ₆ alkylthio group, cyano group, Qa
A phenyl group optionally substituted with Qa, a benzyl group optionally substituted with Qa, a styryl group optionally substituted with Qa, a cinnamyl group optionally substituted with Qa,
A phenethyl group optionally substituted with Qa, a 3-phenylnormalpropyl group optionally substituted with Qa or Q
a represents a benzylthio group which may be substituted, and X represents a cyano group, a nitro group, a (C ₁ -C ₄ alkoxy) carbonyl group, a (C ₁ -C ₄ alkyl) carbonyloxy group, a (C 1
₁ -C ₄ alkoxy) carbonyl group, a methanesulfonyloxy group, a hydroxyl group, an ethynyl group, an amide group, NR ²
R ^3, halogen atom, C ₁ -C ₄ alkyl group, C ₁ -C ₄ haloalkyl group or a phenyl group which may be substituted with Qa, Y is a hydrogen atom, C ₁ -C ₆ alkyl, C ₃
—C ₆ cycloalkyl group, C ₁ -C ₆ haloalkyl group, C ₁
-C ₆ alkoxycarbonyl group, a dimethylaminocarbonyl group, 2-hydroxyethyl group, a methoxymethyl group,
An acetyl group, a methanesulfonyl group, a dimethylaminosulfonyl group, a phenyl group optionally substituted with Qa or a benzyl group optionally substituted with Qa, Z represents an oxygen atom or a sulfur atom, and L represents a single bond Represents a C ₁ -C ₆ alkylene optionally substituted by Qb, a C ₂ -C ₆ alkenylene optionally substituted by Qb or a C ₂ -C ₄ alkynylene optionally substituted by Qb, R ¹ is C ₁ -C ₃ alkyl, X is C _1-
Represents a C ₃ alkyl group or a C ₁ -C ₃ haloalkyl group,
And when Y represents a methyl group and Z represents an oxygen atom, L is a single bond and C _2- optionally substituted by Qb.
C ₆ alkylene, C ₂ optionally substituted by Qb
-C ₆ alkenylene or C ₂ -C ₄ alkynylene which may be substituted by Qb, wherein Qb represents one or more substituents selected from a methyl group, a methoxycarbonyl group, an ethoxycarbonyl group, a cyano group and a phenyl group. ,
n represents 0 or 1, A represents a single bond, CO, SO ₂ or an oxygen atom, and when A represents a single bond, B represents NR ²
Or NR ² NR ³ , when A and L both represent a single bond and X represents a cyano group, B represents an oxygen atom or a sulfur atom, A represents a single bond, and L is substituted by Qb B represents an oxygen atom or a C ₁ -C ₆ alkylene which may be substituted, C ₂ -C ₆ alkenylene which may be substituted by Qb or C ₂ -C ₄ alkynylene which may be substituted by Qb. Represents a sulfur atom,
When A represents CO and B represents NR ^2, when A represents SO ₂ and B represents NR ² or NR ² NR ^3, when A represents an oxygen atom B represents NR _2, A And B may combine to form NR ² CONR ³ , and R ² and R ³ independently of one another are hydrogen, methyl, formyl, (C
₁ -C ₄ alkoxy) carbonyl group, a (C ₁ -C ₄ alkyl) carbonyl group, C ₁ -C ₄ alkylsulfonyl group and a substituted group selected from phenylsulfonyl group. ]
And a herbicide containing the same as an active ingredient.

In the compound of the present invention, AB is NH
In the case of, it means that both tautomers are included as shown in Scheme 1, or that it means an intramolecular hydrogen bond.

[0007]

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When the compound of the present invention has optically active isomers, diastereomers, and geometric isomers, both the respective mixtures and the separated respective isomers are included.

[0009]

BEST MODE FOR CARRYING OUT THE INVENTION Specific substituents in the formula (I) are listed. R represents a phenyl group, a 2-fluorophenyl group, a 3-fluorophenyl group, a 4-fluorophenyl group,
Chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 2-bromophenyl, 3-bromophenyl, 4-chlorophenyl
Bromophenyl group, 2,3-difluorophenyl group, 2,4-difluorophenyl group, 2,5-difluorophenyl group, 3,4-
Difluorophenyl group, 3,5-difluorophenyl group, 2,
3-dichlorophenyl group, 2,4-dichlorophenyl group, 2,5-
Dichlorophenyl group, 3,4-dichlorophenyl group, 3,5-dichlorophenyl group, 2,3-dibromophenyl group, 2,4-dibromophenyl group, 2,5-dibromophenyl group, 3,4-dibromophenyl group, 3 , 5-dibromophenyl group, 2,3,4, -trifluorophenyl group, 2,3,5-trifluorophenyl group,
2,3,6-trifluorophenyl group, 2,4,5-trifluorophenyl group, 3,4,5-trifluorophenyl group, 2,3,4-trichlorophenyl group, 2,3,5-triphenyl group Chlorophenyl group, 2,3,
6-trichlorophenyl group, 2,4,5-trichlorophenyl group, 3,4,5-trichlorophenyl group, 2,3,4-tribromophenyl group, 2,3,5-tribromophenyl group, 2, 3,6-tribromophenyl group, 2,4,5-tribromophenyl group, 3,4,5-
Tribromophenyl, pentafluorophenyl, pentachlorophenyl, 3-chloro-2-fluorophenyl, 4-chloro-2-fluorophenyl, 5-chloro-2-fluorophenyl, 4-chloro-3- Fluorophenyl group, 3-
Chloro-5-fluorophenyl group, 2-chloro-5-fluorophenyl group, 3-chloro-4-fluorophenyl group, 2-chloro-
4-fluorophenyl group, 2-chloro-3-fluorophenyl group, 3-bromo-2-fluorophenyl group, 4-bromo-2-fluorophenyl group, 5-bromo-2-fluorophenyl group, 4-
Bromo-3-fluorophenyl group, 3-bromo-5-fluorophenyl group, 2-bromo-5-fluorophenyl group, 3-bromo-
4-fluorophenyl group, 2-bromo-4-fluorophenyl group, 2-bromo-3-fluorophenyl group, 3-bromo-2-chlorophenyl group, 4-bromo-2-chlorophenyl group, 5-bromo-2- Chlorophenyl group, 4-bromo-3-chlorophenyl group, 3-bromo-5-chlorophenyl group, 2-bromo-5-chlorophenyl group, 3-bromo-4-chlorophenyl group, 2-bromo-
4-chlorophenyl group, 2-bromo-3-chlorophenyl group,
3,4-dichloro-2-fluorophenyl group, 3,4-dichloro-5-
Fluorophenyl group, 3,4-dichloro-6-fluorophenyl group, 2-trifluoromethylphenyl group, 3-trifluoromethylphenyl group, 4-trifluoromethylphenyl group, 2,3-bistrifluoromethylphenyl group, 2,4-bistrifluoromethylphenyl group, 2,5-bistrifluoromethylphenyl group, 3,4-bistrifluoromethylphenyl group, 3,5-bistrifluoromethylphenyl group, 2-fluoro-3-trifluoromethylphenyl Group, 4-fluoro-3-
Trifluoromethylphenyl group, 5-fluoro-3-trifluoromethylphenyl group, 2-fluoro-5-trifluoromethylphenyl group, 2-fluoro-4-trifluoromethylphenyl group, 3-fluoro-4-trifluoro Methylphenyl group, 4-chloro-3-trifluoromethylphenyl group, 3-
Chloro-5-trifluoromethylphenyl group, 2-chloro-4-
Trifluoromethylphenyl group, 3-chloro-4-trifluoromethylphenyl group, 4-bromo-3-trifluoromethylphenyl group, 3-bromo-4-trifluoromethylphenyl group, 2-bromo-4-trifluoro Methylphenyl group, 2,3
-Difluoro-4-trifluoromethylphenyl group, 3,4-difluoro-5-trifluoromethylphenyl group, 3,5-difluoro-4-trifluoromethylphenyl group, 2,3,5,6-tetrafluoro- 4-trifluoromethylphenyl group, 2-methylphenyl group, 3-methylphenyl group, 4-methylphenyl group, 2,3-dimethylphenyl group, 2,4-dimethylphenyl group, 2,5-dimethylphenyl group, 3,4-dimethylphenyl group, 3,5-dimethylphenyl group, 4-fluoro-3-methylphenyl group, 2-fluoro-4-methylphenyl group, 3-fluoro-4-methylphenyl group, 4-chloro- 3-methylphenyl group, 2-chloro-4-methylphenyl group, 3-chloro-4-methylphenyl group, 4-bromo-3-methylphenyl group, 2-bromo-
4-methylphenyl group, 3-bromo-4-methylphenyl group, 2
-Trifluoromethoxyphenyl group, 3-trifluoromethoxyphenyl group, 4-trifluoromethoxyphenyl group, 2,3-bis (trifluoromethoxy) phenyl group,
4-bis (trifluoromethoxy) phenyl group, 2,5-bis (trifluoromethoxy) phenyl group, 3,4-bis (trifluoromethoxy) phenyl group, 3,5-bis (trifluoromethoxy) phenyl group, 4-fluoro-3-trifluoromethoxyphenyl group, 2-fluoro-4-trifluoromethoxyphenyl group, 3-fluoro-4-trifluoromethoxyphenyl group, 4-chloro-3-trifluoromethoxyphenyl group, 2- Chloro-4-trifluoromethoxyphenyl group, 3
-Chloro-4-trifluoromethoxyphenyl group, 4-bromo
-3-trifluoromethoxyphenyl group, 2-bromo-4-trifluoromethoxyphenyl group, 3-bromo-4-trifluoromethoxyphenyl group, 2-cyanophenyl group, 3-cyanophenyl group, 4-cyanophenyl group , 4-chloro-3-nitrophenyl group, 2,4-dinitrophenyl group, 3-methyl-4-nitrophenyl group, 3-isopropylphenyl group, 4-isopropylphenyl group, 3,4-diisopropylphenyl group, 2
-Pyridyl group, 4-fluoro-2-pyridyl group, 5-fluoro-2-pyridyl group, 6-fluoro-2-pyridyl group, 4-
Chloro-2-pyridyl group, 5-chloro-2-pyridyl group, 6
-Chloro-2-pyridyl group, 4-bromo-2-pyridyl group, 5-bromo-2-pyridyl group, 6-bromo-2-pyridyl group, 3,5-difluoro-2-pyridyl group, 4,5- Difluoro-2-pyridyl group, 5,6-difluoro-2-pyridyl group, 3,5-dichloro-2-pyridyl group, 4,5-dichloro-2-pyridyl group, 5,6-dichloro-2-pyridyl group ,
3,5-dibromo-2-pyridyl group, 4,5-dibromo-2-
Pyridyl group, 5,6-dibromo-2-pyridyl group, 5-chloro-3-fluoro-2-pyridyl group, 5-chloro-4-fluoro-2-pyridyl group, 6-chloro-5-fluoro-2- Pyridyl group, 5-bromo-3-fluoro-2-pyridyl group, 5
-Bromo-4-fluoro-2-pyridyl group, 6-bromo-5
-Fluoro-2-pyridyl group, 3-chloro-5-fluoro-2-pyridyl group, 4-chloro-5-fluoro-2-pyridyl group, 5-chloro-6-fluoro-2-pyridyl group, 5-bromo -3-chloro-2-pyridyl group, 5-bromo-4-chloro-2-pyridyl group, 6-bromo-5-chloro-2-pyridyl group, 5-trifluoromethyl-2-pyridyl group, 3-fluoro -5-trifluoromethyl-2-pyridyl group, 4-fluoro-5
-Trifluoromethyl-2-pyridyl group, 6-fluoro-5-trifluoromethyl-2-pyridyl group, 3-chloro-5-trifluoromethyl-2-pyridyl group, 4-chloro-5-trifluoromethyl- 2-pyridyl group, 6-chloro-5-trifluoromethyl-2
-Pyridyl group, 3-bromo-5-trifluoromethyl-2-pyridyl group, 4-bromo-5-trifluoromethyl-2-pyridyl group, 6-bromo-5-trifluoromethyl-2-pyridyl group, 3
-Bromo-5-fluoro-2-pyridyl group, 4-bromo-5
-Fluoro-2-pyridyl group, 5-bromo-6-fluoro-2-pyridyl group, 3-bromo-5-chloro-2-pyridyl group, 4-bromo-5-chloro-2-pyridyl group, 5-bromo -6-chloro-2-pyridyl group, 3-pyridyl group, 5-fluoro-3-pyridyl group, 6-fluoro-3-pyridyl group, 5
-Chloro-3-pyridyl group, 6-chloro-3-pyridyl group, 5-bromo-3-pyridyl group, 6-bromo-3-pyridyl group, 2,6-difluoro-3-pyridyl group, 4,6- Difluoro-3-pyridyl group, 5,6-difluoro-3-pyridyl group, 2,6-dichloro-3-pyridyl group, 4,6-dichloro-3-pyridyl group, 5,6-dichloro-3-pyridyl group ,
2,6-dibromo-3-pyridyl group, 4,6-dibromo-3-
Pyridyl group, 5,6-dibromo-3-pyridyl group, 6-chloro-2-fluoro-3-pyridyl group, 6-chloro-4-fluoro-3-pyridyl group, 6-chloro-5-fluoro-3- Pyridyl group, 6-bromo-2-fluoro-3-pyridyl group, 6
-Bromo-4-fluoro-3-pyridyl group, 6-bromo-5
-Fluoro-3-pyridyl group, 2-chloro-6-fluoro-3-pyridyl group, 4-chloro-6-fluoro-3-pyridyl group, 5-chloro-6-fluoro-3-pyridyl group, 6-bromo -2-chloro-3-pyridyl group, 6-bromo-4-chloro-3-pyridyl group, 6-bromo-5-chloro-3-pyridyl group, 2-bromo-6-fluoro-3-pyridyl group, 4 -Bromo-6-fluoro-3-pyridyl group, 5-bromo-6-fluoro-3-pyridyl group, 2-bromo-6-chloro-3-pyridyl group, 4-bromo-6-chloro-3-pyridyl group , 5-
Bromo-6-chloro-3-pyridyl group, 6-trifluoromethyl-3-pyridyl group, 2-fluoro-6-trifluoromethyl-3-pyridyl group, 4-fluoro-6-trifluoromethyl-3-pyridyl Group, 5-fluoro-6-trifluoromethyl-3-pyridyl group, 2-chloro-6-trifluoromethyl-3-pyridyl group, 4-chloro-6-trifluoromethyl-3-pyridyl group, 5-chloro -6-trifluoromethyl-3-pyridyl group, 2-bromo-6-trifluoromethyl-3-pyridyl group, 4-bromo-6-trifluoromethyl-3-pyridyl group, 5-bromo-6-trifluoro Methyl-3-pyridyl group, 6-methyl-3-pyridyl group, 2-fluoro-6-methyl-3-pyridyl group, 4-fluoro-6-methyl-3-pyridyl group, 5-fluoro-6-
Methyl-3-pyridyl group, 2-chloro-6-methyl-3-pyridyl group, 4-chloro-6-methyl-3-pyridyl group, 5-
Chloro-6-methyl-3-pyridyl group, 2-bromo-6-methyl-3-pyridyl group, 4-bromo-6-methyl-3-pyridyl group, 5-bromo-6-methyl-3-pyridyl group, 4-pyridyl, 2-fluoro-4-pyridyl group, 2-chloro-4-
Pyridyl group, 2-bromo-4-pyridyl group, 2-furyl group, 4-fluoro-2-furyl group, 5-fluoro-2-furyl group, 4-chloro-2-furyl group, 5-chloro-2- Furyl group, 4-bromo-2-furyl group, 5-bromo-2-furyl group, 4,5-difluoro-2-furyl group, 4,5-dichloro-2-furyl group, 4,5-dibromo-2 -Furyl group, 3-furyl group, 5-fluoro-3-furyl group, 5-chloro-3-furyl group, 5-bromo-3-furyl group, 2-thienyl group, 4-
Fluoro-2-thienyl group, 5-fluoro-2-thienyl group, 4-chloro-2-thienyl group, 5-chloro-2-thienyl group, 4-bromo-2-thienyl group, 5-bromo-2-thienyl Group, 4,5-difluoro-2-thienyl group, 4,5-dichloro-2-thienyl group, 4,5-dibromo-2-thienyl group, 3-thienyl group, 5-fluoro-3-thienyl group, 5 −
Chloro-3-thienyl group, 5-bromo-3-thienyl group, 1
-Naphthyl group, 3-fluoro-1-naphthyl group, 4-fluoro-2-naphthyl group, 3-chloro-1-naphthyl group, 4-
Chloro-2-naphthyl group, 3-bromo-1-naphthyl group, 4
-Bromo-2-naphthyl group, 2,4-difluoro-1-naphthyl group, 3,4-difluoro-1-naphthyl group, 2,4-dichloro-1-naphthyl group, 3,4-dichloro-1-naphthyl Group, 2,4-dibromo-1-naphthyl group, 3,4-dibromo-1-naphthyl group, 2-naphthyl group, 4-fluoro-2-
Naphthyl group, 4-chloro-2-naphthyl group, 4-bromo-2
-Naphthyl group, 1,2-dioxymethylene-3-phenyl group, 1,2-dioxymethylene-4-fluoro-3-phenyl group, 1,2-dioxymethylene-5-fluoro-3-phenyl group , 1,2-dioxymethylene-6-fluoro-3-phenyl group, 1,2-dioxymethylene 4-chloro-3-phenyl group, 1,2-dioxymethylene-5-chloro-3-phenyl group , 1,2-dioxymethylene-6-chloro-3-phenyl group, 1,2-dioxymethylene-4-bromo-3-phenyl group, 1,2-dioxymethylene-5-bromo-3-phenyl Group, 1,2-dioxymethylene-6-bromo-3-phenyl group, 1,2-dioxymethylene-4,6-difluoro-
3-phenyl group, 1,2-dioxymethylene-5,6-difluoro-3-phenyl group, 1,2-dioxymethylene-4,
6-dichloro-3-phenyl group, 1,2-dioxymethylene-5,6-dichloro-3-phenyl group, 1,2-dioxymethylene-4,6-dibromo-3-phenyl group, 1,2 -Dioxymethylene-5,6-dibromo-3-phenyl group, 1,2
-Dioxymethylene-4-phenyl group, 1,2-dioxymethylene-6-fluoro-4-phenyl group, 1,2-dioxymethylene-6-chloro-4-phenyl group, 1,2-dioxy Examples include a methylene-6-bromo-4-phenyl group and a hydrogen atom.

As AB, NH, NMe, NCHO,
_{NCOOMe, NCOOEt, NCOMe, NSO 2} M
_{e, NSO 2 Et, NS0 2} Ph, CONH, CONM
e, CONCHO, CONCOOMe, CONCOOE
t, CONCOMe, CONSO ₂ Me, CONSO ₂ E
_{t, CONS0 2 Ph, NHNH,} NHNMe, NHN
CHO, NHNCOOMe, NHNCOOet, NHN
COMe, NHNSO ₂ Me, NHNSO ₂ Et, NHN
_{S0 2 Ph, NMeNH, NMeNMe,} NMeNCH
O, NMeNCOOMe, NMeNCOOet, NMe
NCOMe, NMeNSO ₂ Me, NMeNSO ₂ Et,
NMeNS0 ₂ Ph, SO ₂ NH, SO ₂ NMe, SO ₂ N
_{CHO, SO 2 NCOOMe, SO 2} NCOOEt, SO
₂ NCOMe, SO ₂ NSO ₂ Me, SO ₂ NSO ₂ Et,
_{SO 2 NS0 2 Ph, SO 2} NHNH, SO 2 NHNMe,
SO ₂ NHNCHO, SO ₂ NHNCOOMe, SO ₂ N
HNCOOEt, SO ₂ NHNCOMe, SO ₂ NHNS
O ₂ Me, SO ₂ NHNSO ₂ Et, SO ₂ NHNS 0 ₂ P
h, ONH, ONMe, ONCHO, ONCOOMe,
ONCOOEt, ONCOMe, ONSO ₂ Me, ON
SO ₂ Et, ONSO ₂ Ph, O and S.

R1 is a methyl group, an ethyl group, a normal propyl group, an isopropyl group, a cyclopropyl group, a normal butyl group, an isobutyl group, a secondary butyl group, a cyclobutyl group, a tertiary butyl group, a normal pentyl group, a cyclopentyl group, a norma Ruhexyl group,
Cyclohexyl, methylthio, ethylthio, benzylthio, cyano, phenyl, 2-fluorophenyl, 3-fluorophenyl, 4-fluorophenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl
Chlorophenyl group, 2-bromophenyl group, 3-bromophenyl group, 4-bromophenyl group, 2-methylphenyl group, 3-methylphenyl group, 4-methylphenyl group, 2-methylphenyl group
Methoxyphenyl group, 3-methoxyphenyl group, 4-methoxyphenyl group, 2-trifluoromethylphenyl group, 3
-Trifluoromethylphenyl group, 4-trifluoromethylphenyl group, 2-trifluoromethoxyphenyl group, 3-trifluoromethoxyphenyl group, 4-trifluoromethoxyphenyl group, 2-methylthiophenyl group, 3
-Methylthiophenyl group, 4-methylthiophenyl group, 2
-Methanesulfonylphenyl group, 3-methanesulfonylphenyl group, 4-methanesulfonylphenyl group, 2-methylaminophenyl group, 3-methylaminophenyl group, 4-
Methylaminophenyl group, 2-dimethylaminophenyl group, 3-dimethylaminophenyl group, 4-dimethylaminophenyl group, 2-methoxycarbonylphenyl group, 3-methoxycarbonylphenyl group, 4-methoxycarbonylphenyl group, 2-ethoxy Carbonylphenyl group, 3-ethoxycarbonylphenyl group, 4-ethoxycarbonylphenyl group, 2-nitrophenyl group, 3-nitrophenyl group, 4-nitrophenyl group, 2-cyanophenyl group, 3-
Cyanophenyl group, 4-cyanophenyl group, 2,4-dichlorophenyl group, 2-chloro-4-methanesulfonylphenyl group, 2-methanesulfonyl-4-chlorophenyl group,
2-chloro-3-methoxyethoxy-4-methanesulfonylphenyl group, benzyl group, 2-fluorobenzyl group, 3
-Fluorobenzyl group, 4-fluorobenzyl group, 2-chlorobenzyl group, 3-chlorobenzyl group, 4-chlorobenzyl group, 2-bromobenzyl group, 3-bromobenzyl group,
4-bromobenzyl group, 2-methylbenzyl group, 3-methylbenzyl group, 4-methylbenzyl group, 2-methoxybenzyl group, 3-methoxybenzyl group, 4-methoxybenzyl group, 2-trifluoromethylbenzyl group, 3-trifluoromethylbenzyl group, 4-trifluoromethylbenzyl group, 2-trifluoromethoxybenzyl group, 3-trifluoromethoxybenzyl group, 4-trifluoromethoxybenzyl group, 2-methylthiobenzyl group, 3-methylthiobenzyl Group, 4-methylthiobenzyl group, 2-methanesulfonylbenzyl group, 3-methanesulfonylbenzyl group, 4-
Methanesulfonylbenzyl group, 2-methylaminobenzyl group, 3-methylaminobenzyl group, 4-methylaminobenzyl group, 2-dimethylaminobenzyl group, 3-dimethylaminobenzyl group, 4-dimethylaminobenzyl group, 2-
Methoxycarbonylbenzyl group, 3-methoxycarbonylbenzyl group, 4-methoxycarbonylbenzyl group, 2-
Ethoxycarbonylbenzyl group, 3-ethoxycarbonylbenzyl group, 4-ethoxycarbonylbenzyl group, 2-
Nitrobenzyl group, 3-nitrobenzyl group, 4-nitrobenzyl group, 2-cyanobenzyl group, 3-cyanobenzyl group, 4-cyanobenzyl group, trifluoromethyl group, pentafluoroethyl group, heptafluoro-n-propyl And chlorodifluoromethyl and bromodifluoromethyl groups.

X represents a cyano group, a methoxycarbonyl group, an ethoxycarbonyl group, an amide group, a trifluoromethyl group, a fluorine atom, a chlorine atom, a bromine atom, a nitro group,
Ethynyl group, phenyl group, 2-fluorophenyl group, 3-
Fluorophenyl group, 4-fluorophenyl group, 2-chlorophenyl group, 3-chlorophenyl group, 4-chlorophenyl group, 2-bromophenyl group, 3-bromophenyl group, 4
-Bromophenyl group, 2-methylphenyl group, 3-methylphenyl group, 4-methylphenyl group, 2-methoxyphenyl group, 3-methoxyphenyl group, 4-methoxyphenyl group, 2-trifluoromethylphenyl group, 3 -Trifluoromethylphenyl group, 4-trifluoromethylphenyl group, 2-trifluoromethoxyphenyl group, 3-trifluoromethoxyphenyl group, 4-trifluoromethoxyphenyl group, 2-methylthiophenyl group, 3-methylthiophenyl group , 4-methylthiophenyl group, 2-methanesulfonylphenyl group, 3-methanesulfonylphenyl group, 4-
Methanesulfonylphenyl group, 2-methylaminophenyl group, 3-methylaminophenyl group, 4-methylaminophenyl group, 2-dimethylaminophenyl group, 3-dimethylaminophenyl group, 4-dimethylaminophenyl group, 2-
Methoxycarbonylphenyl group, 3-methoxycarbonylphenyl group, 4-methoxycarbonylphenyl group, 2-
Ethoxycarbonylphenyl group, 3-ethoxycarbonylphenyl group, 4-ethoxycarbonylphenyl group, 2-
Examples include a nitrophenyl group, a 3-nitrophenyl group, a 4-nitrophenyl group, a 2-cyanophenyl group, a 3-cyanophenyl group, and a 4-cyanophenyl group.

Y represents a hydrogen atom, a methyl group, an ethyl group, a normal propyl group, an isopropyl group, a cyclopropyl group, a normal butyl group, an isobutyl group, a secondary butyl group, a cyclobutyl group, a tertiary butyl group,
Normal pentyl group, cyclopentyl group, normal hexyl group, cyclohexyl group, phenyl group, 2-fluorophenyl group, 3-fluorophenyl group, 4-fluorophenyl group, 2-chlorophenyl group, 3-chlorophenyl group,
4-chlorophenyl group, 2-bromophenyl group, 3-bromophenyl group, 4-bromophenyl group, 2-methylphenyl group, 3-methylphenyl group, 4-methylphenyl group, 2
-Methoxyphenyl group, 3-methoxyphenyl group, 4-methoxyphenyl group, 2-trifluoromethylphenyl group, 3-trifluoromethylphenyl group, 4-trifluoromethylphenyl group, 2-trifluoromethoxyphenyl group, 3 -Trifluoromethoxyphenyl group, 4-trifluoromethoxyphenyl group, 2-methylthiophenyl group, 3-methylthiophenyl group, 4-methylthiophenyl group, 2-methanesulfonylphenyl group, 3-methanesulfonylphenyl group, 4-methane Sulfonylphenyl group, 2-
Methylaminophenyl group, 3-methylaminophenyl group, 4-methylaminophenyl group, 2-dimethylaminophenyl group, 3-dimethylaminophenyl group, 4-dimethylaminophenyl group, 2-methoxycarbonylphenyl group, 3-methoxy Carbonylphenyl group, 4-methoxycarbonylphenyl group, 2-ethoxycarbonylphenyl group, 3-ethoxycarbonylphenyl group, 4-ethoxycarbonylphenyl group, 2-nitrophenyl group, 3-nitrophenyl group, 4-nitrophenyl group, 2-cyanophenyl group, 3-cyanophenyl group, 4-cyanophenyl group, benzyl group, 2-fluorobenzyl group, 3-fluorobenzyl group, 4-fluorobenzyl group, 2-chlorobenzyl group,
3-chlorobenzyl group, 4-chlorobenzyl group, 2-bromobenzyl group, 3-bromobenzyl group, 4-bromobenzyl group, 2-methylbenzyl group, 3-methylbenzyl group, 4
-Methylbenzyl group, 2-methoxybenzyl group, 3-methoxybenzyl group, 4-methoxybenzyl group, 2-trifluoromethylbenzyl group, 3-trifluoromethylbenzyl group, 4-trifluoromethylbenzyl group, 2-trimethylbenzyl group Fluoromethoxybenzyl group, 3-trifluoromethoxybenzyl group, 4-trifluoromethoxybenzyl group, 2-methylthiobenzyl group, 3-methylthiobenzyl group, 4-methylthiobenzyl group, 2-methanesulfonylbenzyl group, 3-methanesulfonyl Benzyl group, 4-methanesulfonylbenzyl group, 2-methylaminobenzyl group, 3-methylaminobenzyl group, 4-methylaminobenzyl group, 2-
Dimethylaminobenzyl group, 3-dimethylaminobenzyl group, 4-dimethylaminobenzyl group, 2-methoxycarbonylbenzyl group, 3-methoxycarbonylbenzyl group, 4-methoxycarbonylbenzyl group, 2-ethoxycarbonylbenzyl group, 3-ethoxy Carbonylbenzyl group, 4-ethoxycarbonylbenzyl group, 2-nitrobenzyl group, 3-nitrobenzyl group, 4-nitrobenzyl group,
2-cyanobenzyl, 3-cyanobenzyl and 4-
And a cyanobenzyl group.

Examples of Z include O and S. L and
And CH_Two, CHMe, C (Me)_Two, CH_TwoCH_Two, C
H (Me) CH_Two, C (Me)_TwoCH_Two, CH_TwoCH (M
e), CH (Me) CH (Me), CH_TwoC (Me)_Two,
CH_TwoCH_TwoCH_Two, CH (Me) CH_TwoCH_Two, CH_TwoCH
(Me) CH_Two, CH_TwoCH_TwoCH (Me), CH (M
e) CH (Me) CH_Two, CH (Me) CH_TwoCH (M
e), CH_TwoCH (Me) CH (Me), CH_TwoCH_TwoC
H_TwoCH_Two, CH (Me) CH_TwoCH_TwoCH_Two, CH_TwoCH
(Me) CH_TwoCH_Two, CH_TwoCH_TwoCH (Me) CH_Two,
CH_TwoCH_TwoCH_TwoCH (Me), CH (Me) CH (M
e) CH _TwoCH_Two, CH (Me) CH_TwoCH (Me) C
H_Two, CH (Me) CH_TwoCH_TwoCH (Me), CH_TwoCH
(Me) CH (Me) CH_Two, CH_TwoCH (Me) CH_Two
CH (Me), CH_TwoCH_TwoCH (Me) CH (Me),
CH (COOMe), CH_TwoCH (COOMe) and
CH = CHCH_TwoIs raised.

In the following, Me represents a methyl group and Et represents an ethyl group.

Some of the compounds of the present invention are used as herbicides for upland fields and non-cultivated land, such as Solanum nigrum and Datura stramonium , in both soil treatment and foliage treatment. Solanaceae
(Solanaceae) weeds, Malvaceae weeds represented by scabs (Abutilon theophrasti) , American sika deer (Sida spinosa), etc., and Malva Asagao ( Ipomoea purpu
rea) morning glory such as (Ipomoe a spps.) and Morning Glory acids (Calystegia spps.) family Convolvulaceae represented by such (Conv
olvulaceae) Weeds, Amaranthus lividus ,
Amaranthaceae weeds represented by Amaranthus retroflexus, etc., and Xanthium pen
sylvanicum , ragweed ( Ambrosia artemisiaefoli )
a), sunflower (Helianthus annuus), galinsoga quadriradiata (Ga
linsoga ciliata) , thistle (Cirsium arve)
nse), Novorogi ( Senecio vulgaris ), Himejon
Asteraceae (Composita) represented by ( Erigeron annus )
e) Weeds, dog puppies ( Rorippa indica ), wild puppies ( Sinapis arvensis ), and rapes ( Capsella Bursapast )
oris ), Brassicaceae (Cruciferae) weed, Polygonum Blumei , Polygonu
m convolvulus) and other Polygonaceae (Polygonaceae)
Weeds, Pursaceae (Portulacaceae) weeds represented by purslanes ( Portulaca oleracea ), etc.
odium album) , core kaza ( Chenopodium ficifolium ),
Red crab (Cochia scoparia )
henopodiaceae) weeds, Caryophyllaceae weeds such as Stellaria media, Scrophulariaceae weeds such as Veronica persica , and communis.
a communis ) etc. (Commelinacea
e) Weeds, Labiatae weeds, represented by Lamium amplexicaule , Lamium purpureum, etc. Weeds, Euphorbia supina
Euphorbia maculata, Euphorbia maculata, etc., Euphorbiaceae weed, Galium spurium , Rubia akane, etc., Rubiaceae weed, Viola mand
shurica) and other legumes ( Legumi) such as Violaceae weeds, Sesbania exaltata , and Cassia obtusifolia.
nosae) broad-leaved weeds such as weeds (Broad-leaved weeds), wild sorghum (Sorgham bicolor), fall panicum (Panicum di
chotomiflorum) , Johnsongrass ( Sorghum halepens)
e) , dog millet (Echinochloa crus-galli var. crus-gal
li) , Echinochloa crus-galli var. pra
ticola) , cultivated flies (Echinochloa utilis) , crabgrass ( Digitaria adscendens ), oats ( Avenafatu )
a) , Hawkgrass (Eleusine indica ), Enokorogosa ( Se
taria viridis) , Sparrow-nosed Ephemer ( Alopecurus aegua )
lis) and other grass weeds (Graminaceous weeds)
, Daylily ( Cyperus rotundus, Cyperus esculentus )
Cyperaceous wee (Cyperaceous wee)
ds) and other various field weeds (Cropland weeds) have low herbicide and high herbicidal activity.

[0017] In addition, as a herbicide for paddy fields, in any of soil treatment and foliage treatment under flooded conditions, it is possible to use a hermit mosquito ( Alisma canaliculatum ) or a mosquito ( Sagittaria ).
trifolia) , weeds ( Sagittaria pygmaea ), and other weeds (Alismataceae) weeds; cyperus difformis ; and Cyperus seroti
nus) , Firefly (Scirpus juncoides) , Krogwai ( El
eocharis kuroguwai ) and other Cyperaceae weeds, Azena ( Lindernia pyxidaria )
Scrophulariaceae (Scrothulariaceae) weed, which is represented by an equal, pontederiaceae (Potenderiaceae) weeds represented by Monochoria (Monochoria vaginalis), etc., pondweed (Pota
mogeton distinctus )
amogetonaceae), Lythraceae weed represented by Rotala indica, etc., Echinochloa oryzicola , Echino millet ( Echino )
chloa crus-galli var. formosensis) , barnyardgrass (Echi
nochloa crus-galli var. crus-galli ) Weeds, etc.
Paddy weeds have high herbicidal activity at low dose.

Some of the compounds of the present invention include important crops such as rice, wheat, barley, sorghum, peanuts,
Highly safe against corn, soybeans, cotton, beets, etc. The compound of the present invention can be synthesized, for example, by the methods shown in Schemes 2, 3 and 4. Ra in Schemes 2, 3 and 4 represents a C ₁ -C ₄ alkyl group,
Rb is a protecting group such as a methoxymethyl group and a methoxyethoxymethyl group (for example, Protective Group
s in Organic SynthesisSec
represent equivalent) to that described in ond Edition P14-87, X 'represents a leaving group such as a halogen atom, Ya is hydrogen atom, C ₁ -C ₆ alkyl, C ₃
A C ₆ cycloalkyl group, a Ph group optionally substituted with Qa, a benzyl group optionally substituted with Qa (Qa
Represents the same meaning as above. R1a represents C ₁ -C ₆
Alkyl group, C ₃ -C ₆ cycloalkyl group, C ₁ -C ₆ haloalkyl group or Ph optionally substituted by Qa,, Q
a represents a benzyl group which may be substituted with a, a phenethyl group which may be substituted with Qa, a styryl group which may be substituted with Qa, and a phenylpropyl group which may be substituted with Qa; of an alkali metal, Xa represents C ₁ -C ₄ alkyl group, C ₁ -C ₄ haloalkyl group or a phenyl group which may be substituted with Qa, W represents a dimethylamino group, or ORa, R, O
n, L, X and Y represent the same meaning as described above.

[0019]

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As shown in Scheme 2, the 3-cyano-5-hydroxypyrazole derivative (vi), which is an intermediate of the compound of the present invention, is obtained by reacting oxalacetic diesters (i) with hydrazines to form 3-alkoxycarbonyl. A 5-hydroxypyrazole derivative (ii) can be synthesized by protecting the hydroxy group, followed by an amidation reaction, followed by a dehydration reaction, and a deprotection reaction. Preferable dehydrating agents used at that time include, for example, trichloroacetyl chloride, trifluoroacetyl anhydride, chlorosulfonyl isocyanate, paratoluenesulfonyl chloride, trimethylsilyl chloride, and the like. Are described.

The thus obtained 3-cyano-5-hydroxypyrazole derivative (vi) is reacted with carbonyl chlorides or carboxylic anhydrides to give (vii)
Next, the compound of the present invention can be produced by reacting with (viii) and amines. In addition, as shown in Scheme 3, 5-intermediate which is an intermediate of the compound of the present invention
The hydroxypyrazole derivative (xi) is synthesized by reacting a beta-ketoester derivative (x) with hydrazines,
Hereinafter, the compound of the present invention is obtained in the same manner as described above.

[0022]

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Further, as shown in Scheme 4, the compound of the present invention can be prepared by reacting a 5-hydroxypyrazole derivative (xii) with an orthoacetic acid ester or an N, N-dimethylacetamidodialkyl acetal. After synthesizing the (1-ethylidene) pyrazolin-5-one derivative (xiii), the compound of the present invention is obtained in the same manner as described above.

[0024]

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The synthesis examples of the compounds of the present invention and their intermediates are specifically described below by way of examples, but the present invention is not limited by these examples.

[0026]

【Example】

Example 1 Synthesis of 3-ethoxycarbonyl-5-hydroxy-1-methylpyrazole

[0027]

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50 g of diethyl sodium oxalacetate is added to 50 g
After suspending in 0 ml of ethanol and adding 25 ml of acetic acid at room temperature, 15 g of methylhydrazine was added dropwise over 30 minutes. Thereafter, the mixture was stirred at room temperature for 2.5 hours, and then heated and refluxed for 4.5 hours. After cooling, the solvent was distilled off under reduced pressure, water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with water. Thereafter, the organic layer was dried over anhydrous sodium sulfate, filtered, and the solvent was distilled off under reduced pressure. Water was added to the residue, and the precipitated crystals were filtered under reduced pressure and washed with water to give 3-ethoxycarbonyl-5-hydroxy-.
23 g of 1-methylpyrazole was obtained as a solid. Example 2 Synthesis of 3-ethoxycarbonyl-5-methoxymethoxy-1-methylpyrazole

[0029]

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3-ethoxycarbonyl-5-hydroxy-
Dissolve 60 g of 1-methylpyrazole in 300 ml of dimethylformamide and add 14 g of sodium hydride (60% in
oil) was gradually added, and the mixture was stirred for 5 minutes. Then, 29 g of methoxymethyl chloride was added dropwise, and the mixture was stirred at room temperature overnight. The reaction mixture was poured into ice water, extracted with ethyl acetate, washed with saturated saline, and then dried over anhydrous sodium sulfate. After filtration, the solvent was distilled off, and the residue was washed with hexane to give 3-
62.3 g of ethoxycarbonyl-5-methoxymethoxy-1-methylpyrazole were obtained as a solid. Example 3 Synthesis of 3-amido-5-methoxymethoxy-1-methylpyrazole

[0031]

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To 62.3 g of 3-ethoxycarbonyl-5-methoxymethoxy-1-methylpyrazole, 400 ml of 28% aqueous ammonia was added and stirred at room temperature overnight. After the solvent was completely distilled off under reduced pressure, the residue was washed with diisopropyl ether and washed with 3
-Amido-5-methoxymethoxy-1-methylpyrazole
51.33 g were obtained as a solid. Melting point: 108-110 ° C. Example 4 Synthesis of 3-cyano-5-methoxymethoxy-1-methylpyrazole

[0033]

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30 g of 3-amido-5-methoxymethoxy-1-methylpyrazole was dissolved in 200 ml of methylene chloride, and 50 ml of triethylamine was added. Under ice cooling, 32.4 g of trichloroacetyl chloride was slowly dropped, and the mixture was stirred at room temperature for 6 hours. After the solvent was distilled off under reduced pressure, the residue was extracted with diethyl ether, and the solvent was distilled off under reduced pressure. Crude purification was performed by column chromatography to obtain 29 g of 3-cyano 5-methoxymethoxy-1-methylpyrazole as a liquid.

N _D ^21.4 1.4886 Example 5 Synthesis of 3-cyano-5-hydroxy-1-methylpyrazole

[0036]

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16 g of 3-cyano-5-methoxymethoxy-1-methylpyrazole was dissolved in 100 ml of methanol, 1.5 ml of concentrated hydrochloric acid was added dropwise, and the mixture was refluxed for 2 hours. After cooling, the solvent was distilled off under reduced pressure, and the residue was washed with chloroform to give 3-cyano-5-
8.36 g of hydroxy-1-methylpyrazole was obtained as a solid. Melting point: 182-184 ° C. Example 6 Synthesis of 5-acetyloxy-3-cyano-1-methylpyrazole

[0038]

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After suspending 22.4 g of 3-cyano-5-hydroxy-1-methylpyrazole in 250 ml of dry tetrahydrofuran and adding 13.5 ml of acetyl chloride at room temperature,
Under ice-cooling, 28 ml of triethylamine was added. Then, under ice cooling,
Stir for 45 minutes. After the solvent was distilled off under reduced pressure, water was added, and the mixture was extracted with chloroform. The organic layer was washed with water and saturated saline, dried over anhydrous sodium sulfate, filtered, and then the solvent was distilled off under reduced pressure to obtain 29 g of 5-acetyloxy-3-cyano-1-methylpyrazole.

N _D ^20.9 1.4622 Example 7 Synthesis of 4-acetyl-3-cyano-5-hydroxy-1-methylpyrazole

[0041]

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11.3 g of 5-acetyloxy-3-cyano-1-methylpyrazole was dissolved in dry 1,4-dioxane, 9.5 g of potassium carbonate was added at room temperature, and the mixture was heated under reflux for 2 hours. After cooling, water was added and the mixture was washed with chloroform. Hydrochloric acid was added until the aqueous layer became acidic, the resulting oil was extracted with chloroform, and the organic layer was washed with saturated saline. The organic layer was dried over anhydrous sodium sulfate and filtered, and the solvent was distilled off under reduced pressure.
Ethanol was added to the residue, and the precipitated crystals were filtered under reduced pressure and washed with ethanol to obtain 6 g of 4-acetyl-3-cyano-5-hydroxy-1-methylpyrazole as a solid. Melting point: 147 to 149 ° C. Example 8 Synthesis of 3-cyano-1-methyl-4- [1- (4-trifluoromethylbenzylamino) ethylidene] pyrazolin-5-one (Compound No. 3)

[0043]

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5 g of 4-acetyl-3-cyano-5-hydroxy-1-methylpyrazole was suspended in 100 ml of ethanol, and 4.3 ml of 4-trifluoromethylbenzylamine was added at room temperature, followed by heating under reflux for 1 hour. After cooling, the solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography.
Thereafter, n-hexane was added, and the precipitated crystals were filtered under reduced pressure and washed with normal hexane to give 3-cyano-1.
7 g of -methyl-4- [1- (4-trifluoromethylbenzylamino) ethylidene] pyrazolin-5-one were obtained as a solid. Example 9 Synthesis of 5-hydroxy-1-methyl-3-trifluoromethylpyrazole

[0045]

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Ethyl trifluoromethyl acetoacetate (200 g) was dissolved in ethanol (100 ml), methyl hydrazine (54 g) was added dropwise at 0 ° C. over 20 minutes, and the mixture was refluxed for 14 hours. After cooling, the solvent was distilled off under reduced pressure, and the obtained crystals were collected by filtration under reduced pressure and washed with chloroform.
91 g of 5-hydroxy-1-methyl-3-trifluoromethylpyrazole was obtained as an individual. Example 10 Synthesis of 1-methyl-3-trifluoromethyl-4- [1- (4-chlorophenethylamino) ethylidene] pyrazolin-5-one (Compound No. 28)

[0047]

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2 g of 5-hydroxy-1-methyl-3-trifluoromethylpyrazole was dried in 10 ml of tetrahydrofuran.
Then, 1.5 g of dimethylacetamide dimethyl acetal was added dropwise, and the mixture was stirred at room temperature overnight. In addition, 4
1.9 g of -chlorophenethylamine was added, the mixture was stirred overnight, and the solvent was distilled off under reduced pressure. Purified by column chromatography (developing solvent: chloroform) as it is,
1-Methyl-3-trifluoromethyl-4- [1- (4-chlorophenethylamino) ethylidene] pyrazolin-5-one was obtained as a solid.

The structural formulas and physical properties of the compounds of the present invention synthesized according to the above Examples are shown in Tables 1 and 2, respectively.
The results are shown in Tables 2, 3 and 4. [Table 1]

[0050]

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[0051]

TABLE 1 ──────────────────────────────────── compound ^{R 0n-L R 1 X Y} ─ ─────────────────────────────────── 1 4-CF ₃ -Ph CH ₂ Me CN Ph 2 4- CF ₃ -Ph CH ₂ Me Ph Ph 3 4-CF ₃ -Ph CH ₂ Me CN Me 4 4-CF ₃ -Ph CH ₂ Me COOEt Me 5 4-Cl-Ph (CH ₂ ) ₂ Me COOEt Me 6 4- CF ₃ -Ph CH ₂ Me Br Ph 7 4-Cl-Ph (CH ₂ ) ₂ Me Br Ph 8 4-CF ₃ -Ph CH ₂ Me CONH ₂ Me 9 3,4-Cl ₂ -Ph (CH ₂ ) ₂ Me CN Me 10 3,4-Cl ₂ -Ph CH ₂ Me CN Me 11 2,4-Cl ₂ -Ph (CH ₂ ) ₂ Me CN Me 12 4-CF ₃ -Ph CH ₂ Et CN Me 13 4-CF ₃ -Ph CH ₂ Me Ph Me 14 4-CF ₃ -Ph CH ₂ Me 4-F-Ph Me 15 4-CF ₃ -Ph CH ₂ Me 3,4-Cl ₂ -Ph Me 16 H CH ₂ Me 4- F-Ph Me 17 H (CH ₂ ) ₅ Me 3,4-Cl ₂ -Ph Me 18 3,4-Cl ₂ -Ph CH ₂ i-Pr CN Me 19 3,4-Cl ₂ -Ph CH ₂ Et CN Me 20 Ph-Me CF ₃ Me 21 4-CF ₃ -Ph-Me CF ₃ Me 22 4-CF ₃ -Ph CH ₂ Me CF ₃ Et 23 4-CF ₃ -Ph CH ₂ Me CF ₃ Ph ──── ──────────── ───────────────────

[0052]

TABLE 2 ──────────────────────────────────── Compound ^{R 0n-L R 1 X Y} ─ ─────────────────────────────────── 24 4-CF ₃ -Ph CH ₂ Me CF ₃ i-Pr 25 4-CF ₃ -Ph CH ₂ Me CF ₃ n-Bu 26 2-Cl-Ph (CH ₂ ) ₂ Me CF ₃ Me 27 3-Cl-Ph (CH ₂ ) ₂ Me CF ₃ Me 28 4-Cl- Ph (CH ₂ ) ₂ Me CF ₃ Me 29 Ph (CH ₂ ) ₃ Me CF ₃ Me 30 H CH ₂ C (Me) ₂ CH ₂ Me CF ₃ Me 31 4-pyridyl CH ₂ Me CF ₃ Me 32 3-Cl -Ph NH Me CF ₃ Me 33 Ph CH = CHCH ₂ Me CF ₃ Me 34 4-F-Ph (CH ₂ ) ₂ Me CF ₃ Me 35 4-Cl-Ph CH ₂ CH (Me) Me CF ₃ Me 36 3 , 4-Cl ₂ -Ph (CH ₂ ) ₂ Me CF ₃ Me 37 Ph (CH ₂ ) ₄ Me CF ₃ Me 38 H (CH ₂ ) ₇ Me CF ₃ Me 39 4-Me-Ph (CH ₂ ) ₂ Me CF ₃ Me 40 4-MeO-Ph (CH ₂ ) ₂ Me CF ₃ Me 41 2, 4-Cl ₂ -Ph (CH ₂ ) ₂ Me CF ₃ Me 42 4-CF ₃ -Ph CH ₂ Me CF ₃ CH ₂ Ph 43 3, 4-Cl ₂ -Ph (CH ₂ ) ₂ Me CF ₃ CH ₂ Ph 44 Ph CH ₂ O Me CF ₃ Me 45 H (CH ₂ ) ₇ Me CF ₃ CH ₂ Ph 46 EtO (CH ₂ ) ₂ Me CF ₃ CH ₂ Ph ────────────────────────────────────

[0053]

TABLE 3 ──────────────────────────────────── Compound ^{R 0n-L R 1 X Y} ─ ─────────────────────────────────── 47 4-CF ₃ -Ph CH ₂ Me CF ₃ t-Bu 48 3,4-Cl ₂ -Ph (CH ₂ ) ₂ Me CF ₃ t-Bu 49 Ph (CH ₂ ) ₂ Me CF ₃ Me 50 4-CF ₃ -Ph CH ₂ PhCH ₂ CF ₃ Me 51 4-Cl- Ph (CH ₂ ) ₂ Me CF ₃ CF ₂ Me 52 2-thienyl CH ₂ Me CF ₃ Me 53 2-furyl CH ₂ Me CF ₃ Me 54 4-Cl-Ph (CH ₂ ) ₂ PhCH ₂ CF ₃ Me 55 H CH ₂ PhCH ₂ CF ₃ Me 56 4-CF ₃ -Ph CH ₂ 4-Cl-PhCH ₂ CF ₃ Me 57 H CH ₂ 4-Cl-PhCH ₂ CF ₃ Me 58 1,2-dioxymethylene CH ₂ Me CF ₃ Me -4-Ph 59 4-NO ₂ -Ph CH ₂ Me CF ₃ Me 60 4-CF ₃ -Ph CH ₂ Me t-Bu Me 61 3, 4-Cl ₂ -Ph (CH ₂ ) ₂ Me c- Pr Me 62 3,4-Cl ₂ -Ph (CH ₂ ) ₂ Et CN Me 63 3,4-Cl ₂ -Ph (CH ₂ ) ₂ i-Pr CN Me 64 4-CF ₃ -Ph CH ₂ i-Pr CN Me 65 3,4-Cl ₂ -Ph CH ₂ n-Pr CN Me 66 3,4-Cl ₂ -Ph CH ₂ c-Pr CN Me 67 4-CF ₃ -Ph CH ₂ c-Pr CN Me 68 3 , 4-Cl ₂ -Ph (CH ₂ ) ₂ c-Pr CN Me ──────────────────────────────────── [Table-2 ]

[0054]

[Table 4] 化合物 Compound No. Physical properties ──── ──────────────────────────────── 1 mp 157-161 ° C 2 mp 149-152 ° C 3 mp 115-117 ° C 4 mp 130-132 ° C 5 n _D ^20.3 1.4661 6 mp 164-166 ° C 7 mp 143-145 ° C 8 mp 174-176 ° C 9 mp 140-142 ° C 10 mp 153-155 ° C 11 mp 184-186 ° C 12 mp 93-95 ° C 13 mp 169-171 ° C 14 mp 182-184 ° C 15 mp 163-165 ° C 16 mp 152-154 ° C 17 mp 83-85 ° C 18 mp 47-49 ° C 19 mp 146-148 ° C 20 mp 108 -110 ° C ^{_{1 mp 142-144 ℃ 22 n D 20.4}} 1.5176 ────────────────────────────────────

[0055]

[Table 5] 化合物 Compound No. Physical properties ──── ──────────────────────────────── 23 mp 145-147 ° C 24 mp 107-110 ° C 25 mp 92-95 ° C ^{_{26 mp 96-100 ℃ 27 n D 20.5}} 1.5571 28 mp 148-153 ℃ 29 n D 20.5 1.5500 30 n D 20.5 1.4401 31 mp 131-133 ℃ 32 mp 176-178 ℃ 33 n D 20.3 1 _{.4211 34 mp 157-159 ℃ 35 n D} 20.3 1.4447 36 mp 151-153 ℃ 37 mp 34- 36 ℃ 38 n D 19.8 1.4998 39 mp 104-106 ℃ 40 mp 54- 56 ℃ 41 mp 155- 157 ° C 42 mp 93-95 ° C 4 3 mp 97- 99 ℃ 44 mp 125-126 ℃ 45 n D 20.0 1.4836 ─────────────────────────────── ─────

[0056]

[Table 6] 化合物 Compound No. Physical properties ──── ４６ 46 mp 49-51 ° C 47 mp 102-104 ° C 48 mp 78-80 ° C 49 mp 81-82 ° C 50 mp 90-91 ° C 51 mp 55-57 ° C 52 mp 107-109 ° C 53 mp 78-80 ° C 54 mp 99-101 ° C 55 mp 115-118 ° C 56 n _D ^21.4 1.56457 mp 163-165 ° C 58 mp 149-151 ° C 59 mp 176-178 ° C 60 mp 131-133 ° C 61 mp 135-137 ° C 62 mp 129-131 ° C 63 mp 111-113 ° C 64 mp 33-35 ° C 65 mp119 −121 66 mp 139-141 ° C 67 mp 82-84 ° C 68 mp 126-128 ° C ──────────────────────────────── ──── [Table-3]

[0057]

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[0058]

[Table 7] Compound No. R ¹ Y ──────────────────────────────────── (II) -1 Me Me (II)- 2 Et Me (II) -3 i-Pr Me (II) -4 n-Pr Me (II) -5 c-Pr Me (II) -6 4-Cl-PhCH = CH Me ───────────────────────────── [Table-4]

[0059]

[Table 8] Compound No. Physical properties ──────────────────────────────────── (II) -1 mp 147-149 ° C ( II) -2 mp 126-128 ° C (II) -3 mp 77-79 ° C (II) -4 mp 90-92 ° C (II) -5 mp 123-125 ° C (II) -6 mp 187-189 ° C ─────────────────────────────────── In the table, Me represents a methyl group and Et represents an ethyl group. , I-
Pr represents an isopropyl group, c-Pr represents a cyclopropyl group, n-Pr represents a normal propyl group, and Ph represents a phenyl group.

The compounds of the present invention synthesized according to the above schemes or Examples are shown in Tables 5 and 6 including the above Examples.
And Table-7, but the present invention is not limited by these. [Table-5]

[0061]

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[0062]

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[0063]

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[0064]

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[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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[0070]

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[0071]

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[0072]

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[0073]

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[0074]

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[0075]

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[0076]

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[0077]

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[0078]

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[0079]

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[0080]

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[0081]

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[0082]

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[0083]

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[0084]

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[0085]

[Table 9] {R-On-L-} ────────────────────────────────PhCH ₂ , 2-F-PhCH ₂ , 3-F-PhCH ₂ , 4 _{-F-PhCH 2, 2-Cl} -PhCH 2, 3-Cl-PhCH 2, 4-Cl-PhCH 2, 2-Br-PhCH 2, 3-Br-PhCH 2, 4-Br-PhCH 2, 2, _{4-F 2 -PhCH 2, 3,4} -F 2 -PhCH 2, 2,4-Cl 2 -PhCH 2, 3,4 -Cl 2 -PhCH 2, 3,4,5-F 3 -PhCH 2, _{3,4,5-Cl 3 -PhCH 2, 2} -F-4-Cl-PhCH 2, 3-F-4-Cl-PhCH 2, 3-Cl-4-F-P hCH 2, 2-Cl- 4-Br-PhCH ₂ , 3-Cl-4-Br-PhCH ₂ , 3-Br-4 _{-Cl-PhCH 2, 2-F} -3,4-Cl 2 -PhCH 2, 3,4-Cl 2 -5-F-PhCH 2, 3,4-Cl 2 - 6-F-PhCH 2, 2- _{CF 3 -PhCH 2, 3-CF} 3 -PhCH 2, 4-CF 3 -PhCH 2, 2,4- (CF 3) 2 -PhCH 2, 3,4- (CF 3) 2 -PhCH 2, 2- _{F-3-CF 3 -PhCH 2} , 3-CF 3 -4-F-PhCH 2, 3-CF 3 -5-F -PhCH 2, 3-CF 3 -6-F-PhCH 2, 2-F- _{4-CF 3 -PhCH 2, 3} -F-4-CF 3 -PhCH 2, 3-CF 3 -4-Cl-PhCH 2, 2-Cl-4-CF 3 -PhCH 2, 3-Cl-4 - _{CF 3 -PhCH 2, 3-CF} 3 -4-Br-PhCH 2, 2-Br-4-CF 3 -PhCH 2, 3-Br-4 -CF 3 -PhCH 2, 2,3-F 2 -4 _{-CF 3 -PhCH 2, 3,4-F} 2 -5-CF 3 -P _{hCH 2, 2,3,5,6-F 4 -4} -CF 3 -PhCH 2, 2-Me-PhCH 2, 3-Me-PhCH 2, 4-Me-PhCH 2, ─────── ─────────────────────────────

[0086]

[Table 10] {R-On-L-} ──────────────────────────────── 2,4-Me ₂ -PhCH ₂ , 3,4-Me ₂ -PhCH _{2, 3-Me-4-} F-PhCH 2, 2-F-4-Me-PhCH 2, 3-F-4-Me-P hCH 2, 3-Me-4-Cl-PhCH 2, 2-Cl _{-4-Me-PhCH 2, 3} -Cl-4-M e-PhCH 2, 2-CF 3 O-PhCH 2, 3-CF 3 O-PhCH 2, 4-CF 3 O-PhCH 2 2,4- _{(CF 3 O) 2 -PhCH 2} , 3,4- (CF 3 O) 2 -PhCH 2, 3-CF 3 O-4-F-PhCH 2, 2-F-4-CF 3 O-PhCH 2, 3-F-4-C F 3 O-PhCH 2, 3-CF 3 O-4-Cl-PhCH 2, 2-Cl-4 _{-CF 3 O-PhCH 2, 3} -Cl -4-CF 3 O-PhCH 2, 2-CN-PhCH 2, 3-CN-PhCH 2, 4-CN-PhCH 2, 2-NO 2 -4-Cl -PhCH ₂ , 2,4- (NO ₂ ) ₂ -PhCH ₂ , 3-NO ₂ -4-Me-PhCH ₂ , 3-Me-4-NO ₂ -PhCH ₂ , 3-i-Pr-PhCH ₂ , _{4 -i-Pr-PhCH 2,} 3,4- (i-Pr) 2 -PhCH 2, PhCH 2 CH 2, 2-F-PhCH 2 CH 2, 3-F-PhCH 2 CH 2, 4-F- _{P hCH 2 CH 2, 2-} Cl-PhCH 2 CH 2, 3-Cl-PhCH 2 CH 2, 4-Cl -PhCH 2 CH 2, 2-Br-PhCH 2 CH 2, 3-Br-PhCH 2 CH 2 _{, 4- Br-PhCH 2 CH 2} , 2,4-F 2 -PhCH 2 CH 2, 3,4-F 2 -PhCH 2 CH 2, 2,4-Cl 2 -Ph CH 2 C _{2, 3,4-Cl 2 -PhCH 2} CH 2, 3,4,5-F 3 -PhCH 2 CH 2, 3,4,5-Cl 3 -PhCH 2 CH 2, ──────── ────────────────────────────

[0087]

[Table 11] {R-On-L-} ──────────────────────────────── 2-F-4-Cl-PhCH_TwoCH_Two, 3-F-4-Cl-PhCH_TwoCH_Two, 3-Cl-4-F-PhCH_TwoCH_Two, 2-Cl-4-Br-PhCH_TwoCH_Two, 3-Cl-4-Br-PhCH_TwoCH_Two, 3-Br-4-Cl-PhCH_TwoCH_Two, 2-F-3,4-Cl_Two-PhCH_TwoCH_Two, 3,4-Cl_Two-5-F-PhCH_TwoCH_Two, 3,4-Cl_Two-6-F-PhCH_TwoCH_Two, 2-CF_Three-PhCH_TwoCH_Two, 3-CF_Three-PhCH_TwoCH_Two, 4-CF_Three-PhCH_Two CH_Two, 2,4 -− (CF_Three)_Two-PhCH_TwoCH_Two, 3,4-(CF_Three)_Two-PhCH_TwoCH_Two, 2-F-3-CF_Three-PhCH_TwoCH_Two, 3-CF_Three-4-F-PhCH_TwoCH_Two, 3-CF_Three-5-F-PhCH_TwoCH_Two, 3-CF_Three-6-F-PhCH_TwoCH_Two, 2-F-4-CF_Three-PhCH_TwoCH_Two, 3-F-4-CF_Three-PhCH_TwoCH_Two, 3-CF_Three-4-Cl-PhCH_TwoCH_Two, 2-Cl-4-CF_Three-PhCH_TwoCH_Two, 3-CF_Three-4-Br-PhCH_TwoCH_Two, 2-Br-4-CF_Three-PhCH_TwoCH_Two, 3-Br-4-CF_Three-PhCH_TwoCH_Two, 2,3-F_Two−4-CF_Three-PhCH_TwoCH_Two, 3,4-F_Two-5-CF_Three-PhCH_TwoCH_Two 2,3,5,6-F_Four−4-CF_Three-PhCH_TwoCH_Two, 2-Me-PhCH_TwoCH_Two, 3-Me-PhCH_TwoCH_Two, 4-Me-PhCH_TwoCH _Two , 2,4-Me_Two-PhCH_TwoCH_Two, 3,4-Me_Two-PhCH_TwoCH_Two, 3-Me-4-F-PhCH_TwoCH_Two, 2-F-4-Me-PhCH_TwoCH_Two, 3-F-4-Me-PhCH_TwoCH_Two, 3-Me-4-Cl-PhCH_TwoCH_Two, 2-Cl-4-Me-PhCH_TwoCH_Two, 3-Cl-4-Me-PhCH_TwoCH_Two, ────────────────────────────────────

[0088]

[Table 12] {R-On-L-} ──────────────────────────────── 2-CF_ThreeO-PhCH_TwoCH_Two, 3-CF_ThreeO-PhCH_TwoCH_Two, 4-CF_ThreeO-Ph CH_TwoCH_Two, 2,4 -− (CF_ThreeO)_Two-PhCH_TwoCH_Two, 3,4-(CF_ThreeO)_Two-PhCH_TwoCH_Two, 3-CF_ThreeO-4-F-PhCH_TwoCH_Two, 2-F-4-CF_ThreeO-PhCH_TwoCH_Two, 3-F-4-CF_ThreeO-PhCH_TwoCH_Two, 3-CF_ThreeO-4-Cl-PhCH_TwoCH_Two, 2-Cl-4-CF_ThreeO-PhCH_TwoCH_Two , 3-Cl-4-CF_ThreeO-PhCH_TwoCH_Two, 2-CN-PhCH_TwoCH_Two, 3-CN-PhCH_TwoCH_Two, 4-CN-PhCH_TwoCH _Two , 2-NO_Two-4-Cl-PhCH_TwoCH_Two, 2,4- (NO_Two)_Two-PhCH_TwoCH_Two, 3-NO_Two-4-Me-PhCH_TwoCH_Two, 3-Me-4-NO_Two-PhCH_TwoCH_Two, 3-i-Pr-PhCH_TwoCH_2,4-i-Pr-PhCH_TwoCH_2,3,4- (i-Pr)_Two-P hCH_TwoCH_Two, PhCH_TwoCH_TwoCH_Two, 2-F-PhCH_TwoCH_TwoCH_Two, 3-F-PhCH_TwoCH_TwoCH_Two, 4-F-PhCH_TwoCH_TwoCH_Two, 2-Cl-PhCH_TwoCH_TwoCH_Two, 3-Cl-PhCH_TwoCH_TwoCH_Two, 4-Cl-PhCH_TwoCH_TwoCH_Two, 2-Br-PhCH_TwoCH_TwoCH_Two, 3-Br-PhCH_TwoCH_TwoCH_Two, 4-Br-PhCH_TwoCH_TwoCH_Two, 2,4-F_Two-PhCH_TwoCH_TwoCH_Two, 3,4-F_Two-PhCH_TwoCH_TwoCH_Two, 2,4-Cl_Two-PhCH_TwoCH_TwoCH_Two, 3,4-Cl_Two-PhCH_TwoCH_TwoCH_Two, 3,4,5-F_Three -PhCH_TwoCH_TwoCH_Two, 3,4,5-Cl_Three-PhCH_TwoCH_TwoCH_Two, 2-F-4-Cl-PhCH_TwoCH_TwoCH_Two, 3-F-4-Cl-PhCH_TwoCH_TwoCH_Two, 3-Cl-4-F-PhCH_TwoCH_TwoCH_Two, ────────────────────────────────────

[0089]

[Table 13] {R-On-L-} ──────────────────────────────── 2-Cl-4-Br-PhCH_TwoCH_TwoCH_Two, 3-Cl-4-Br-PhCH_TwoCH_Two CH_Two, 3-Br-4-Cl-PhCH_TwoCH_TwoCH_Two, 2-F-3,4-Cl_Two-PhCH_TwoCH_TwoCH_Two, 3,4-Cl_Two-5-F-PhCH_TwoCH _Two CH_Two, 3,4-Cl_Two-6-F-PhCH_TwoCH_TwoCH_Two, 2-CF_Three-PhCH_TwoCH_TwoCH_Two, 3-CF_Three-PhCH_TwoCH_TwoCH_Two, 4-CF_Three− PhCH_TwoCH_TwoCH_Two, 2,4 -− (CF_Three)_Two-PhCH_TwoCH_TwoCH_Two, 3,4-(CF_Three)_Two-PhCH_TwoCH_TwoCH_Two , 2-F-3-CF_Three-PhCH_TwoCH_TwoCH_Two, 3-CF_Three-4-F-PhCH_TwoCH_TwoCH_Two, 3-CF_Three-5-F-PhCH_TwoCH_TwoCH_Two, 3-CF_Three-6-F-PhCH_TwoCH_TwoCH_Two, 2-F-4-CF_Three-PhCH_TwoCH_TwoCH_Two, 3-F-4-CF_Three-PhCH_TwoCH_TwoCH_Two, 3-CF_Three-4-Cl-PhCH_TwoCH_TwoCH_Two, 2-Cl-4-CF_Three-PhCH_TwoCH _Two CH_Two, 3-Cl-4-CF_Three-PhCH_TwoCH_TwoCH_Two, 3-CF_Three-4-Br-PhCH_TwoCH_TwoCH_Two, 2-Br-4-CF_Three-PhCH_TwoCH _Two CH_Two, 3-Br-4-CF_Three-PhCH_TwoCH_TwoCH_Two, 2,3-F_Two−4-CF_Three-PhCH_TwoCH_TwoCH_Two, 3,4-F_Two-5-CF_Three-PhCH_TwoCH_TwoCH_Two, 2, 3, 5, 6-F_Four−4-CF_Three-PhCH_TwoCH_TwoCH_Two, 2-Me-PhCH_TwoCH_TwoCH_Two, 3-Me-PhCH_TwoCH_TwoCH_Two, 4-Me-P hCH_TwoCH_TwoCH_Two, 2,4- (Me)_Two-PhCH_TwoCH_TwoCH_Two, 3,4- (Me)_Two-P hCH_TwoCH_TwoCH_Two, 3-Me-4-F-PhCH_TwoCH_TwoCH_Two, 2-F-4-Me-PhCH_TwoCH_TwoCH_Two, ────────────────────────────────────

[0090]

[Table 14] {R-On-L-} ──────────────────────────────── 3-F-4-Me-PhCH_TwoCH_TwoCH_Two, 3-Me-4-Cl-PhCH_TwoCH_TwoCH_Two, 2-Cl-4-Me-PhCH_TwoCH_Two CH_Two, 3-Cl-4-Me-PhCH_TwoCH_TwoCH_Two, 2-CF_ThreeO-PhCH_TwoCH_TwoCH_Two, 3-CF_ThreeO-PhCH_TwoCH_TwoCH_Two, 4-CF_ThreeO-PhCH_TwoCH_Two CH_Two, 2,4 -− (CF_ThreeO)_Two-PhCH_TwoCH_TwoCH_Two, 3,4-(CF_ThreeO)_Two-PhCH_TwoCH_Two CH_Two, 3-CF_ThreeO-4-F-PhCH_TwoCH_TwoCH_Two, 2-F-4-CF_ThreeO-PhCH_TwoCH _Two CH_Two, 3-F-4-CF_ThreeO-PhCH_TwoCH_TwoCH_Two, 3-CF_ThreeO-4-Cl-PhCH_TwoCH_TwoCH_Two, 2-Cl-4-CF_ThreeO-PhCH_Two CH_TwoCH_Two, 3-Cl-4-CF_ThreeO-PhCH_TwoCH_TwoCH_Two, 2-CN-PhCH_TwoCH_TwoCH_Two, 3-CN-PhCH_TwoCH_TwoCH_Two, 4-CN-P hCH_TwoCH_TwoCH_Two, 2-NO_Two-4-Cl-PhCH_TwoCH_TwoCH_Two, 2,4- (NO_Two)_Two-PhCH_TwoCH_TwoCH_Two, 3-NO_Two-4-Me-PhCH_TwoCH_TwoCH_Two, 3-Me-4-NO_Two-PhCH_TwoCH_TwoCH_Two, 3-i-Pr-PhCH_TwoCH_TwoCH_2,4-i-Pr-PhCH_TwoCH_TwoCH_2,3,4- (i-Pr)_Two-PhCH_TwoCH_TwoCH_2, PhCH (Me), 2-F-PhCH (Me), 3-F-PhCH (Me), 4-F-PhCH (Me), 2-Cl-PhCH (Me), 3-Cl-PhCH (Me), 4-Cl-PhCH (Me), 2-Br-PhCH (Me), 3-Br-PhCH (Me), 4-Br-PhCH (Me), 2,4-F_Two-PhCH (Me), 3,4-F_Two−PhCH (Me), ────────────────────────────────────

[0091]

[Table 15] {R-On-L-} ──────────────────────────────── 2,4-Cl ₂ -PhCH (Me), 3,4-Cl ₂ -PhCH (Me), 3,4,5-F 3 -PhCH (Me), 3,4,5-Cl 3 -PhCH (Me), 2-F-4-Cl-PhCH (Me), 3-F -4-Cl-PhCH (Me), 3-Cl-4-F-PhCH (Me), 2-Cl-4-Br-PhCH (Me), 3-Cl-4-Br-PhCH (Me), 3-Br-4-Cl- PhCH (Me), 2-F-3,4-Cl 2 -PhCH (Me), 3,4-Cl 2 -5-F-PhCH (Me), 3,4-Cl _{2 -6-F-PhCH (Me} ), 2-CF 3 -PhCH (Me), 3-CF 3 -PhC _{(Me), 4-CF 3} -PhC H (Me), 2,4- (CF 3) 2 -PhCH (Me), 3,4- (CF 3) 2 -PhCH (Me), 2-F-3 _{-CF 3 -PhCH (Me), 3} -CF 3 -4-F-PhCH (Me), 3 -CF 3 -5-F-PhCH (Me), 3-CF 3 -6-F-PhCH (Me) _{, 2- F-4-CF 3} -PhCH (Me), 3-F-4-CF 3 -PhCH (Me) 3-C F 3 -4-Cl-PhCH (Me), 2-Cl-4-CF _{3 -PhCH (Me), 3- Cl} -4-CF 3 -PhCH (Me), 3-CF 3 -4-Br-PhCH (Me), 2 -Br-4-CF 3 -PhCH (Me), 3 _{-Br-4-CF 3 -PhCH (} Me), 2-F-3-F-4-CF 3 -PhCH (Me), 3-F-4-F-5-CF 3 -PhC H (Me), _{2,3,5,6-F 4 -4-CF 3} -Ph CH (Me), 2-Me -PhCH (Me), 3-Me-PhCH (Me), 4-Me-PhCH (Me), 2,4-Me 2 -PhCH (Me), 3,4-Me 2 −PhCH (Me), ────────────────────────────────────

[0092]

[Table 16] {R-On-L-} ──────────────────────────────── 3-Me-4-F-PhCH (Me), 2-F-4 -Me-PhCH (Me), 3-F-4-Me-PhCH (Me), 3-Me-4-Cl-PhCH (Me), 2-Cl-4-Me-PhCH (Me), 3-Cl -4-Me-PhCH (Me), 2-CF_ThreeO-PhCH (Me), 3-CF_ThreeO-PhCH (Me), 4-CF_ThreeO-PhCH (Me), 2,4- (CF_ThreeO)_Two-PhCH (Me), 3,4- (CF_ThreeO)_Two-PhCH (Me), 3-CF_ThreeO-4-F-PhCH (Me), 2-F-4-CF_ThreeO-PhCH (Me), 3-F-4-CF_ThreeO-PhCH (Me), 3-CF_ThreeO-4-Cl-PhCH (Me), 2-Cl-4-CF_ThreeO-PhCH (Me), 3-Cl-4-CF_ThreeO-PhCH (Me), 2-CN-PhCH (Me), 3-CN-PhCH (Me), 4-CN-PhCH (Me), 2-NO_Two-4-Cl -PhCH (Me), 2,4- (NO_Two)_Two-PhCH (Me), 3-NO_Two-4-Me-PhCH (Me), 3-Me-4-NO_Two-PhCH (Me), 3-i-Pr-PhCH (Me), 4-i-Pr-PhCH (Me), 3,4- (i-Pr)_Two-PhCH (Me), PhC (Me)_Two, 2-F-PhC (Me)_Two, 3-F-PhC (Me)_Two, 4-F-PhC (Me)_Two, 2-Cl-PhC (Me)_Two, 3-Cl-PhC (Me)_Two, 4-Cl-PhC (Me)_Two, 2-Br-PhC (Me)_Two, 3-Br-PhC (Me) _Two , 4-Br-PhC (Me)_Two, 2,4-F_Two-PhC (Me)_Two, 3,4-F_Two-PhC (Me)_Two, ────────────────────────────────────

[0093]

[Table 17] {R-On-L-} ──────────────────────────────── 2,4-Cl ₂ -PhC (Me) ₂ , 3,4-Cl _{2 -PhC (Me) 2, 3,4,5} -F 3 -PhC (Me) 2, 3,4,5-Cl 3 -PhC (Me) 2, 2-F-4-Cl-PhC (Me) _{2, 3-F-4-} Cl-PhC (Me) 2, 3-C l-4-F-PhC (Me) 2, 2-Cl-4-Br-PhC (Me) 2, 3-Cl- 4 _{-Br-PhC (Me) 2,} 3-Br-4-Cl-PhC (Me) 2, 2-F-3,4-Cl 2 -PhC (Me) 2, 3,4-Cl 2 -5-F _{-PhC (Me) 2, 3,4-} Cl 2 -6-F-PhC (Me) 2, 2-CF 3 -PhC (Me) 2, 3-CF 3 -PhC _{Me) 2, 4-CF 3} -PhC (Me) 2, 2,4- (CF 3) 2 -PhC (Me) 2, 3,4- (CF 3) 2 -PhC (Me) 2, 2-F _{-3-CF 3 -PhC (Me)} 2, 3-CF 3 -4-F-PhC (Me) 2, 3- CF 3 -5-F-PhC (Me) 2, 3-CF 3 -6-F _{-PhC (Me) 2, 2-} F- 4-CF 3 -PhC (Me) 2, 3-F-4-CF 3 -PhC (Me) 2, 3-CF 3 -4-Cl-PhC (Me) _{2, 2-Cl-4-} CF 3 -PhC (Me) 2, 3-Cl-4-CF 3 -PhC (Me) 2, 3-CF 3 -4-Br-PhC (Me) 2, 2-Br _{-4-CF 3 -PhC (Me)} 2, 3-Br-4-CF 3 -PhC (Me) 2, 2-F-3-F-4-CF 3 -PhC (Me) 2, 3-F- _{4-F-5-CF 3} -PhC (Me) 2, 2,3,5,6-F 4 -4-CF 3 -P hC (Me) ₂ , 2-Me-PhC (Me) ₂ , 3-Me-PhC (Me) ₂ , 4-Me-PhC (Me) ₂ , ───────────── ───────────────────────

[0094]

[Table 18] {R-On-L-} ──────────────────────────────── 2,4-Me ₂ -PhC (Me) ₂ , 3,4-Me _{2 -PhC (Me) 2, 3} -Me-4-F-PhC (Me) 2, 2-F-4-Me-PhC (Me) 2, 3-F -4-Me-PhC (Me) 2, 3-Me-4-Cl- PhC (Me) 2, 2-Cl-4-Me-PhC (Me) 2, 3 -Cl-4-Me-PhC (Me) 2, 2-CF 3 O-PhC ( _{Me) 2, 3-CF 3} O-PhC (Me) 2, 4-CF 3 O-P hC (Me) 2, 2,4- (CF 3 O) 2 -PhC (Me) 2, 3,4- _{(CF 3 O) 2 -PhC (} Me) 2, 3-CF 3 O-4-F-PhC (Me) 2, 2-F-4-CF 3 O- _{PhC (Me) 2, 3-} F-4-CF 3 O-PhC (Me) 2, 3-CF 3 O-4-Cl-PhC (Me) 2, 2-Cl-4-CF 3 O-PhC ( _{Me) 2, 3-Cl-} 4-CF 3 O-PhC (Me) 2, 2-CN-PhC (Me) 2, 3- CN-PhC (Me) 2, 4-CN-PhC (Me) 2, _{2-NO 2 -4-Cl-} PhC (Me) 2, 2,4- (NO 2) 2 -PhC (Me) 2, 3 -NO 2 -4-Me-PhC (Me) 2, 3-Me- _{4-NO 2 -PhC (Me)} 2, 3 -i-Pr-PhC (Me) 2, 4-i-Pr-PhC (Me) 2, 3,4- (i-P r) 2 -PhC (Me _{) 2, PhCH (Me) CH} 2, 2-F-PhCH (Me) CH 2, 3-F-PhCH (M e) CH 2, 4-F-PhCH (Me) CH 2, 2-Cl-PhCH ( _{Me) CH 2, 3-Cl} -Ph _{H (Me) CH 2, 4} -Cl-PhCH (Me) CH 2, 2-B r-PhCH (Me) CH 2, 3-Br-PhCH (Me) CH 2, 4-Br-Ph CH (Me) CH ₂ , ────────────────────────────────────

[0095]

[Table 19] {R-On-L-} ──────────────────────────────── 2,4-F_Two-PhCH (Me) CH_Two, 3,4-F_Two-PhCH (Me) CH_Two, 2,4-Cl_Two-PhCH (Me) CH_Two, 3,4-Cl_Two-PhCH (Me) CH_Two, 3,4,5-F_Three-PhCH (Me) CH_Two, 3,4,5-Cl_Three-PhCH (Me) CH_Two, 2-F-4-Cl-PhCH (Me) CH_Two, 3-F-4-Cl-PhCH (Me) CH_Two, 3-Cl-4-F-PhCH (Me) CH_Two, 2-Cl-4-Br-PhCH (Me) CH_Two, 3-Cl-4-Br-PhCH (Me) CH_Two, 3-Br-4-Cl-PhCH (Me) CH_Two, 2-F-3,4-Cl_Two-PhCH (Me) CH_Two, 3,4-Cl_Two-5-F-PhCH (Me) CH_Two, 3,4-Cl_Two-6-F-PhCH (Me) CH_Two, 2-CF_Three-PhCH (Me) CH_Two, 3-CF_Three-PhCH (Me) CH_Two, 4-CF_Three-PhCH (Me) CH_Two, 2,4 -− (CF_Three)_Two-PhCH (Me) CH_Two, 3,4-(CF_Three)_Two-PhCH (Me) CH_Two, 2-F-3-CF_Three-PhCH (Me) CH_Two, 3-CF_Three-4-F-PhCH (Me) CH_Two, 3-CF_Three-5-F-PhCH (Me) CH_Two, 3-CF_Three-6-F-PhCH (Me) CH_Two, 2-F-4-CF_Three-PhCH (Me) CH_Two, 3-F-4-CF _Three -PhCH (Me) CH_Two, 3-CF_Three-4-Cl-PhCH (Me) CH_Two, 2-Cl-4-CF_Three-PhCH (Me) CH_Two, 3-Cl-4-CF_Three-PhCH (Me) CH_Two, 3-CF_Three-4-Br-PhCH (Me) CH_Two, 2-Br-4-CF_Three-PhCH (Me) CH_Two, 3-Br-4-CF_Three-PhCH (Me) CH_Two, 2,3-F_Two−4-CF_Three-PhCH (Me) CH_Two, ────────────────────────────────────

[0096]

[Table 20] {R-On-L-} ──────────────────────────────── 3,4-F ₂ -5-CF ₃ -PhCH (Me) CH _{2 , 2,3,5,6-F 4 -4-CF} 3 -PhCH (Me) CH 2, 2-Me-PhCH (Me) CH 2, 3-Me-PhCH (Me) CH 2, 4-Me - _{PhCH (Me) CH 2, 2,4} -Me 2 -PhCH (Me) CH 2, 3,4-Me 2 -PhCH (Me) CH 2, 3-Me-4-F-PhCH (Me) CH 2, 2-F-4-Me- PhCH (Me) CH 2, 3-F-4-Me-PhCH (Me) CH 2, 3-Me-4-Cl-PhCH (Me) CH 2, 2-Cl-4 -Me-PhCH (Me) CH ₂ , 3-Cl-4-Me-Ph _{CH (Me) CH 2, 2} -CF 3 O-PhCH (Me) CH 2, 3-CF 3 O-PhCH (Me) CH 2, 4 -CF 3 O-PhCH (Me) CH 2, 2,4- _{(CF 3 O) 2 -PhCH (} Me) CH 2, 3,4- (CF 3 O) 2 -PhCH (M e) CH 2, 3-CF 3 O-4-F-PhCH (Me) CH 2, _{2-F-4-CF 3} O-PhCH (Me) CH 2, 3-F-4-CF 3 O-PhCH (Me) CH 2, 3-CF 3 O-4-Cl-PhCH (Me) CH 2 , 2-Cl-4-CF 3 O-PhC H (Me) CH 2, 3-Cl-4-CF 3 O-PhCH (Me) CH 2, 2-CN-PhCH (Me) CH 2, 3-CN _{-PhCH (Me) CH 2, 4} -CN -PhCH (Me) CH 2, 2-NO 2 -4-Cl-PhCH (Me) CH 2, 2,4- (NO 2) 2 -PhCH (Me) CH _{2, 3-NO 2 -4-} Me-PhCH (Me) CH 2, 3-Me-4-NO 2 - PhCH (Me) CH 2, 3-i-Pr-PhCH (Me) CH 2, 4-i _{-Pr- PhCH (Me) CH 2,} 3,4- (i-Pr) 2 -PhCH (Me) CH 2, ────────────────────── ──────────────

[0097]

[Table 21] {R-On-L-} ──────────────────────────────── PhCH_TwoCH (Me), 2-F-PhCH_TwoCH (Me), 3-F-PhCH_TwoCH (Me), 4-F-PhCH_TwoCH (Me), 2-Cl-PhCH_TwoCH (Me), 3-Cl-PhCH_TwoCH (Me), 4-Cl-PhCH_TwoCH (Me), 2-Br-PhCH_TwoCH (Me), 3-Br-PhCH_TwoCH (Me), 4-Br-Ph CH_TwoCH (Me), 2,4-F_Two-PhCH_TwoCH (Me), 3,4-F_Two-PhCH _Two CH (Me), 2,4-Cl_Two-PhCH_TwoCH (Me), 3,4-Cl_Two-PhCH _Two CH (Me), 3,4,5-F_Three-PhCH_TwoCH (Me), 3,4,5-Cl_Three-Ph CH_TwoCH (Me), 2-F-4-Cl-PhCH_TwoCH (Me), 3-F-4-Cl-PhCH_TwoCH (Me), 3-Cl-4-F-PhCH_TwoCH (Me), 2-Cl-4-Br-PhCH_Two CH (Me), 3-Cl-4-Br-PhCH_TwoCH (Me), 3-Br-4-Cl-PhCH_TwoCH (Me), 2-F-3,4-Cl_Two-PhCH_TwoCH (Me), 3,4-Cl_Two-5-F-PhCH_TwoCH (Me), 4,5Cl_Two-2-F-PhCH_TwoCH (Me), 2-CF_Three-PhCH_TwoCH (Me), 3-CF_Three-PhCH_TwoCH (Me), 4-CF_Three-PhCH_TwoCH (Me), 2,4- (CF_Three)_Two-PhCH_TwoCH (Me), 3,4- (CF_Three)_Two-PhCH_TwoCH (Me), 2-F-3-CF_Three-PhCH_TwoCH (Me), 3-CF_Three-4-F-PhCH_TwoCH (Me), 3-CF_Three-5-F-PhCH_TwoCH (Me), 3-CF_Three-6-F-Ph CH_TwoCH (Me), 2-F-4-CF_Three-PhCH_TwoCH (Me), 3-F-4-CF_Three-PhCH_TwoCH (Me), 3-CF_Three-4-Cl-PhCH_TwoCH (Me), ────────────────────────────────────

[0098]

[Table 22] {R-On-L-} ──────────────────────────────── 2-Cl-4-CF 3 -PhCH 2 CH (Me), 3- _{Cl-4-CF 3 -PhCH 2} CH (Me), 3-CF 3 -4-Br-PhCH 2 CH (Me), 2-Br-4-CF 3 -PhCH 2 C H (Me), 3-Br _{-4-CF 3 -PhCH 2 CH (} Me), 2,3-F 2 -4-CF 3 -PhCH 2 CH (Me), 3,4-F 2 -5-CF 3 -PhCH 2 CH (Me) _{, 2,3,5,6-F 4 -4-CF} 3 -PhCH 2 CH (Me), 2-Me-PhCH 2 CH (Me), 3-Me-PhCH 2 CH (Me), 4-Me - _{PhCH 2 CH (Me), 2,4} -Me 2 -PhCH 2 CH (Me _{, 3,4-Me 2 -PhCH 2 CH} (Me), 3-Me-4-F-PhCH 2 CH (Me), 2-F-4-Me-PhCH 2 CH (M e), 3-F- _{4-Me-PhCH 2 CH (} Me), 3-Me-4-Cl-PhCH 2 CH (Me), 2-Cl-4-Me-PhCH 2 CH (Me), 3-Cl-4-Me-PhCH _{2 CH (Me), 2-} CF 3 O-PhCH 2 CH (Me), 3-CF 3 O-PhCH 2 CH (Me), 4 -CF 3 O-PhCH 2 CH (Me), 2,4- ( _{CF 3 O) 2 -PhCH 2 CH} (Me), 3,4- (CF 3 O) 2 -PhCH 2 CH (Me), 3-CF 3 O-4-F-PhCH 2 CH (Me), 2- _{F-4-CF 3 O-} PhCH 2 C H (Me), 3-F-4-CF 3 O-PhCH 2 CH (Me), 3-CF 3 O-4-Cl-PhCH 2 CH (Me), 2-Cl _{-4-CF 3 O-PhC H} 2 CH (Me), 3-Cl-4-CF 3 O-PhCH 2 CH (Me), 2-CN-PhCH 2 CH (Me), 3-CN-PhCH 2 CH (Me), ────────────────────────────────────

[0099]

[Table 23] {R-On-L-} ──────────────────────────────── 4-CN-PhCH ₂ CH (Me), 2-NO ₂ -4- _{Cl-PhCH 2 CH (Me)} , 2,4- (NO 2) 2 -PhCH 2 CH (Me), 3-NO 2 -4-Me-PhCH 2 CH (Me), 3-Me-4-NO 2 _{- PhCH 2 CH (Me),} 3-i-Pr-PhCH 2 CH (Me), 4-i-Pr- PhCH 2 CH (Me), 3,4- (i-Pr) 2 -PhCH 2 CH (Me ), PhCH ₂ C (Me) ₂ , 2-F-PhCH ₂ C (Me) ₂ , 3-F-PhCH ₂ C (Me) ₂ , 4-F-PhCH ₂ C (Me) ₂ , 2-Cl- _{PhCH 2 C (Me) 2,} 3- Cl-PhCH 2 C ( _{e) 2, 4-Cl-} PhCH 2 C (Me) 2, 2-Br-Ph CH 2 C (Me) 2, 3-Br-PhCH 2 C (Me) 2, 4-Br-PhCH 2 C (Me _{) 2, 2,4-F 2 -PhCH} 2 C (Me) 2, 3,4-F 2 -PhCH 2 C (Me) 2, 2,4- Cl 2 -PhCH 2 C (Me) 2, 3, _{4-Cl 2 -PhCH 2 C (} Me) 2, 3,4,5-F 3 -PhCH 2 C (Me) 2, 3,4,5-Cl 3 -PhCH 2 C (Me) 2, 2-F _{-4-Cl-PhCH 2 C (} Me) 2, 3-F-4-Cl-PhCH 2 C (Me) 2, 3-Cl-4-F-PhCH 2 C (Me) 2, 2-Cl-4 _{-Br-PhCH 2 C (Me)} 2, 3-Cl-4-Br-PhCH 2 C (Me) 2, 3-Br-4-Cl-P hCH 2 C (Me) 2, 2-F-3, _{4-Cl 2 -PhCH 2 C (} Me) 2, 3,4-Cl 2 - _{5-F-PhCH 2 C (} Me) 2, 3,4-Cl 2 -6-F-PhCH 2 C (Me) 2, 2-CF 3 -PhCH 2 C (Me) 2, 3-CF 3 -PhCH ₂ C (Me) ₂ , 4-CF ₃ -PhCH ₂ C (Me) ₂ , 2,4- (CF ₃ ) ₂ -PhCH ₂ C (Me) ₂ , ──────────── ────────────────────────

[0100]

[Table 24] {R-On-L-} ────────────────────────────────3,4- (CF ₃ ) ₂ -PhCH ₂ C (Me) ₂ , _{2-F-3-CF 3} -PhCH 2 C (Me) 2, 3-CF 3 -4-F-PhCH 2 C (M e) 2, 3-CF 3 -5-F-PhCH 2 C (Me) _{2, 3-CF 3 -6-} F-PhCH 2 C (Me) 2, 2-F-4-CF 3 -PhCH 2 C (Me) 2, 3-F-4-CF 3 -P hCH 2 C ( _{Me) 2, 3-CF 3} -4-Cl-PhCH 2 C (Me) 2, 2-Cl-4-CF 3 -PhCH 2 C (Me) 2, 3-Cl-4-CF 3 -PhCH 2 C (Me) ₂ , 3-CF ₃ -4-Br-PhCH ₂ C (Me) ₂ , 2-Br-4-CF ₃ -PhCH _{2 C (Me) 2, 3-} Br-4-CF 3 -PhCH 2 C (Me) 2, 2,3-F 2 -4-CF 3 -PhCH 2 C (Me) 2, 3,4-F 2 - _{5-CF 3 -PhCH 2 C (} Me) 2, 2,3,5,6-F 4 -4-CF 3 -PhCH 2 C (Me) 2, 2-Me-PhCH 2 C (Me) 2, 3 _{-Me-PhCH 2 C (Me)} 2, 4-Me- PhCH 2 C (Me) 2, 2,4-Me 2 -PhCH 2 C (Me) 2, 3,4-Me 2 -PhCH 2 C (Me _{) 2, 3-Me-4} -F-PhCH 2 C (Me) 2, 2-F-4-Me-PhCH 2 C (Me) 2, 3-F-4-Me-PhCH 2 C (Me) 2 , 3-Me-4-Cl -PhCH 2 C (Me) 2, 2-Cl-4-Me-PhCH 2 C (Me) 2, 3-Cl-4-Me-PhCH 2 C (Me) 2, 2 —CF ₃ O—PhCH ₂ C (Me) ₂ , 3-CF ₃ O-PhCH ₂ C (Me) ₂ , 4-CF ₃ O-PhCH ₂ C (Me) ₂ , 2,4- (CF ₃ O) ₂ -PhCH ₂ C (Me) ₂ , 3,4- (CF ₃ O) ₂ -PhCH ₂ C (Me) ₂ , ────────────────────────────────────

[0101]

[Table 25] {R-On-L-} ──────────────────────────────── 3-CF_ThreeO-4-F-PhCH_TwoC (Me)_Two, 2-F-4-CF_ThreeO-PhCH_TwoC (Me)_Two, 3-F-4-CF_ThreeO-PhCH_TwoC (Me)_Two, 3-CF_ThreeO-4-Cl-PhCH_TwoC (Me)_Two, 2-Cl-4-CF_ThreeO-PhCH _Two C (Me)_Two, 3-Cl-4-CF_ThreeO-PhCH_TwoC (Me)_Two, 2-CN-PhCH_TwoC (Me)_Two, 3-CN-PhCH_TwoC (Me)_Two, 4-CN-PhCH_TwoC (Me)_Two, 2-NO_Two-4-Cl-PhCH_TwoC (Me)_Two, 2,4- (NO_Two)_Two-PhCH_TwoC (Me)_Two, 3-NO_Two-4-Me-PhCH_TwoC (Me)_Two, 3-Me-4-NO_Two-Ph CH_TwoC (Me)_Two, 3-i-Pr-PhCH_TwoC (Me)_Two, 4-i-Pr-PhCH_TwoC (Me)_Two, 3,4- (i-Pr)_Two-PhCH_TwoC (Me)_Two, PhCH (COOMe), 2-F-PhCH (COOMe), 3-F-PhCH (COOMe), 4-F-PhCH (COOMe), 2-Cl-PhCH (COOMe), 3-Cl-PhCH (COOMe) ), 4-Cl-PhCH (COOMe), 2-Br-PhCH (COOMe), 3-Br-PhCH (COOMe), 4-Br-PhCH (COOMe), 2,4-F_Two-PhCH (COOMe), 3,4-F_Two-PhCH (COOMe), 2,4-Cl_Two-PhCH (COOMe), 3,4-Cl_Two-PhCH (COOMe), 3,4,5-F_Three-PhCH (COOMe), 3,4,5-Cl_Three-PhCH (COOM e), 2-F-4-Cl-PhCH (COOMe), 3-F-4-Cl-PhCH (COO Me), 3-Cl-4-F-PhCH (COOMe), 2-Cl -4-Br-PhCH (COOMe), 3-Cl-4-Br-PhCH (COOMe), ────────────────────────── ──────────

[0102]

[Table 26] {R-On-L-} ──────────────────────────────── 3-Br-4-Cl-PhCH (COOMe), 2-F-3 _{, 4-Cl 2 -PhCH (COOMe} ), 3,4-Cl 2 -5-F-PhCH (COOMe), 3,4-Cl 2 -6-F-PhCH (COOMe), 2-CF 3 -PhCH ( _{COOMe), 3-CF 3 -PhCH} (COOMe), 4- CF 3 -PhCH (COOMe), 2,4- (CF 3) 2 -PhCH (COOMe), 3,4- (CF 3) 2 -PhCH ( COO Me), 2-F- 3-CF 3 -PhCH (COOMe), 3-CF 3 -4-F-PhCH (CO OMe), 3-CF 3 -5-F-PhCH (COOMe), 3-CF ₃ -6 F-Ph CH (COOMe), 2-F-4-CF 3 -PhCH (COOMe), 3-F-4- CF 3 -PhCH (COOMe), 3-CF 3 -4-Cl-PhCH (COOMe), _{2-Cl-4-CF 3} -PhCH (COOMe), 3-Cl-4-CF 3 -PhCH (COOMe), 3-CF 3 -4-Br-PhCH (COOMe), 2-Br-4-CF 3 -PhCH (COOMe), 3-Br -4-CF 3 -PhCH (COOMe), 2-F-3-F-4-CF 3 -PhCH (COOMe), 3-F-4-F-5-CF 3 - PhCH (COOMe), 2,3,5,6- F 4 -4-CF 3 -PhCH (COOMe), 2-Me-PhCH (COOMe), 3-Me-PhCH (COOMe), 4-M e- PhCH (COOMe), 2,4-Me ₂ -PhCH (COOMe), 3, _{4- Me 2 -PhCH (COOMe),} 3-Me-4-F-PhCH (COOMe), 2-F-4-Me-PhCH (COO Me), 3-F-4-Me-PhCH (COOMe), ────────────────────────────────────

[0103]

[Table 27] {R-On-L-} ──────────────────────────────── 3-Me-4-Cl-PhCH (COOMe), 2-Cl-4 -Me-PhCH (COOMe), 3-Cl-4-Me-PhCH (COOMe), 2-CF_ThreeO-PhCH (COOMe), 3-CF_ThreeO-PhCH (COOMe), 4-CF_ThreeO-PhCH (COOMe), 2,4- (CF_ThreeO)_Two-PhCH (COOMe), 3,4- (CF_ThreeO)_Two-PhCH (COOMe), 3-CF_ThreeO-4-F-PhCH (COOMe), 2-F-4-CF_ThreeO-PhCHC OOMe), 3-F-4-CF_ThreeO-PhCH (COOMe), 3-CF_ThreeO-4-Cl-PhCH (COOMe), 2-Cl-4-CF_ThreeO-PhCH (COOMe), 3-Cl-4-CF_ThreeO-PhCH (COOMe), 2-CN-PhCH (COOMe), 3-CN-PhCH (COOMe), 4-CN-PhCH (COOMe), 2-NO_Two-4-Cl-PhCH (COOMe), 2,4- (NO_Two)_Two-PhCH (COOMe), 3-NO_Two-4-Me-PhCH (COOMe), 3-Me-4-NO _Two -PhCH (COOMe), 3-i-Pr-PhCH (COOMe), 4-i-Pr-PhCH (COOMe), 3,4- (i-Pr)_Two-PhCH (COOMe), PhCH_TwoCH (COOMe), 2-F-PhCH_TwoCH (COOMe), 3-F-PhCH_TwoCH (COOMe), 4-F-PhCH_TwoCH (COOMe), 2-Cl-PhCH_TwoCH (COOMe), 3-Cl-PhCH_TwoCH (COOMe), 4-Cl-PhCH_TwoCH (COOMe), 2-Br-PhCH_TwoCH (COOMe), 3-Br-PhCH_TwoCH (COOMe), 4-Br-PhCH_TwoCH (COO Me), 2,4-F_Two-PhCH_TwoCH (COOMe), 3,4-F_Two-PhCH_TwoCH (COOMe), 2,4-Cl_Two-PhCH_TwoCH (COOMe), ────────────────────────────────────

[0104]

[Table 28] {R-On-L-} ──────────────────────────────── 3,4-Cl_Two-PhCH_TwoCH (COOMe), 3,4,5-F_Three-PhCH_TwoCH (COOMe), 3,4,5-Cl_Three-PhCH_TwoCH (COOMe), 2-F-4-Cl-PhCH_TwoCH (COOMe), 3-F-4-Cl-PhCH_TwoCH (COOMe), 3-Cl-4-F-PhCH_TwoCH (COOMe), 2-Cl-4-Br-PhCH_TwoCH (COOMe), 3-Cl-4-Br-PhCH_TwoCH (COOMe), 3-Br-4-Cl-PhCH_TwoCH (COOMe), 2-F-3,4-Cl_Two-PhCH_TwoCH (COOMe), 3,4-Cl_Two-5-F-Ph CH_TwoCH (COOMe), 3,4-Cl_Two-6-F-PhCH_TwoCH (COOMe), 2-CF_Three-PhCH_TwoCH (COOMe), 3-CF_Three-PhCH_TwoCH (COO Me), 4-CF_Three-PhCH_TwoCH (COOMe), 2,4- (CF_Three)_Two-PhCH_TwoCH (COOMe), 3,4- (CF_Three)_Two-PhCH_TwoCH (COOMe), 2-F-3-CF_Three-PhCH_TwoCH (COOMe), 3-CF_Three -4-F-PhCH_TwoCH (COOMe), 3-CF_Three-5-F-PhCH_TwoCH (COOMe), 3-CF_Three-6-F-PhCH_TwoCH (COOMe), 2-F-4-CF _Three -PhCH_TwoCH (COOMe), 3-F-4-CF_Three-PhCH_TwoCH (COO Me), 3-CF_Three-4-Cl-PhCH_TwoCH (COOMe), 2-Cl-4-CF_Three-Ph CH_TwoCH (COOMe), 3-Cl-4-CF_Three-PhCH_TwoCH (COOMe), 3-CF_Three-4-Br-PhCH_TwoCH (COOMe), 2-Br-4-CF_Three-P hCH_TwoCH (COOMe), 3-Br-4-CF_Three-PhCH_TwoCH (COOMe), 2,3-F_Two−4-CF_Three-PhCH_TwoCH (COOMe), 3,4-F_Two-5-CF_Three -PhCH_TwoCH (COOMe), ────────────────────────────────────

[0105]

[Table 29] {R-On-L-} _{──────────────────────────────── 2,3,5,6-F 4 -4-CF} 3 -PhCH 2 CH (COOMe), 2-Me -PhC H 2 CH (COOMe), 3-Me-PhCH 2 CH (COOMe), 4-Me-P hCH 2 CH (COOMe), 2,4-Me 2 -PhCH 2 CH _{(COOMe), 3,4-Me 2} -PhCH 2 CH (C OOMe), 3-Me-4-F-PhCH 2 CH (COOMe), 2-F-4-Me -PhCH 2 CH (COOMe), 3 _{-F-4-Me-PhCH 2} CH (COOMe), 3-Me-4-Cl-PhCH 2 CH (COOMe), 2-Cl-4-Me-P hCH 2 CH (COOMe), 3 _{-Cl-4-Me-PhCH 2} CH (COOMe), 2-CF 3 O-PhCH 2 CH (COOMe), 3-CF 3 O-PhCH 2 CH (CO OMe), 4-CF 3 O-PhCH 2 CH (COOMe), 2,4- (CF ₃ O) ₂ -PhCH ₂ CH (COOMe), 3,4- (CF ₃ O) ₂ -PhCH ₂ CH (COOMe), 3-CF ₃ O-4-F _{-PhCH 2 CH (COOMe), 2} -F-4-CF 3 O-PhCH 2 CH (COOMe), 3-F-4-CF 3 O-PhC H 2 CH (COOMe), 3-CF 3 O-4 _{-Cl-PhCH 2 CH (COOMe)} , 2-Cl-4-CF 3 O-PhCH 2 CH (COOMe), 3-Cl-4-CF 3 O -PhCH 2 CH (COOMe), 2-CN-PhCH 2 CH (COOMe), 3- CN- PhCH 2 CH (COOMe), 4-CN- PhCH ₂ CH (COOMe), 2-NO ₂ -4-Cl-PhCH ₂ CH (COOMe), 2,4- (NO ₂ ) ₂ -PhCH ₂ CH (COOMe), 3-NO ₂ -4-Me- _{PhCH 2 CH (COOMe), 3} -Me-4-NO 2 -PhCH 2 CH (COOMe), 3-i-Pr-PhCH 2 C H (COOMe), 4-i-Pr-PhCH 2 CH (COOMe), 3,4- (i-Pr) ₂ -PhCH ₂ CH (COOMe), ──────────────────────────────── ────

[Table-6]

[0107]

Embedded image

[0108]

[Table 30] {R-On-L-} ────────────────────────────────PhCH ₂ CH ₂ , 2-F-PhCH ₂ CH ₂ , 3-F- _{PhCH 2 CH 2, 4-F} -P hCH 2 CH 2, 2-Cl-PhCH 2 CH 2, 3-Cl-PhCH 2 CH 2, 4-Cl -PhCH 2 CH 2, 2-Br-PhCH 2 CH 2 _{, 3-Br-PhCH 2 CH} 2, 4- Br-PhCH 2 CH 2, 2,4-F 2 -PhCH 2 CH 2, 3,4-F 2 -PhCH 2 CH 2, 2,4-Cl 2 - _{Ph CH 2 CH 2, 3,4-} Cl 2 -PhCH 2 CH 2, 3,4,5-F 3 -PhCH 2 CH 2, 3,4,5-Cl 3 -PhCH 2 CH 2, 2-F- _{4-Cl-PhCH 2 CH 2} , 3-F-4-Cl-P _{CH 2 CH 2, 3-Cl} -4-F-PhCH 2 CH 2, 2-Cl-4-Br-PhCH 2 CH 2, 3-Cl-4- Br-PhCH 2 CH 2, 3-Br-4- _{Cl-PhCH 2 CH 2, 2} -F-3-Cl-4-Cl-PhCH 2 CH 2, 3-Cl-4-Cl-5-F-PhC H 2 CH 2, 3-Cl-4-Cl- _{6-F-PhCH 2 CH 2} 2-CF 3 -PhCH 2 CH 2, 3-CF 3 -PhCH 2 CH 2, 4-CF 3 -PhCH 2 CH 2 2,4- (CF 3) 2 -PhCH 2 CH _{2, 3,4- (CF 3) 2} -PhCH 2 CH 2 2-F-3-CF 3 -PhCH 2 CH 2, 3-CF 3 -4-F-PhCH 2 CH 2, 3-C F 3 - _{5-F-PhCH 2 CH 2} , 3-CF 3 -6-F-PhCH 2 CH 2, 2-F-4- CF 3 -PhCH 2 CH 2, 3-F-4-CF 3 -PhCH 2 CH 2 3-CF ₃ -4-Cl _{-PhCH 2 CH 2, 2-Cl} -4-CF 3 -PhCH 2 CH 2, 3 -Cl-4-CF 3 -PhCH 2 CH 2 3-CF 3 -4-Br-PhCH 2 CH 2, 2-Br _{-4-CF 3 -PhCH 2 CH 2} , 3 -Br-4-CF 3 -PhCH 2 CH 2 2,3-F 2 -4-CF 3 -PhCH 2 CH 2, 3,4-F 2 -5- CF ₃ -PhCH ₂ CH ₂ ────────────────────────────────────

[0109]

[Table 31] {R-On-L-} ──────────────────────────────── 2, 3, 5, 6-F_Four−4-CF_Three-PhCH_TwoCH_Two 2-Me-PhCH_TwoCH_Two, 3-Me-PhCH_TwoCH_Two, 4-Me-PhCH_TwoCH _Two 2,4-Me_Two-PhCH_TwoCH_Two, 3,4-Me_Two-PhCH_TwoCH_Two, 3-Me-4-F-PhCH_TwoCH_Two, 2-F-4-Me-PhCH_TwoCH_Two, 3-F-4-Me-PhCH_TwoCH_Two, 3-Me-4-Cl-PhCH_TwoCH_Two, 2-Cl-4-Me-PhCH_TwoCH_Two, 3-Cl-4-Me-PhCH_TwoCH_Two, 2-CF_ThreeO-PhCH_TwoCH_Two, 3-CF_ThreeO-PhCH_TwoCH_Two, 4-CF_ThreeO-Ph CH_TwoCH_Two 2,4 -− (CF_ThreeO)_Two-PhCH_TwoCH_Two, 3,4- (CF_ThreeO)_Two-PhCH_TwoCH_Two , 3-CF_ThreeO-4-F-PhCH_TwoCH_Two, 2-F-4-CF_ThreeO-PhCH_TwoCH_Two, 3-F-4-CF_ThreeO-PhCH_TwoCH_Two, 3-CF_ThreeO-4-Cl-PhCH_TwoCH_Two, 2-Cl-4-CF_ThreeO-PhCH_TwoCH_Two , 3-Cl-4-CF_ThreeO-PhCH_TwoCH_Two, 2-CN-PhCH_TwoCH_Two, 3-CN-PhCH_TwoCH_Two, 4-CN-PhCH_TwoCH _Two 2-NO_Two-4-Cl-PhCH_TwoCH_Two, 2-NO_Two-4-NO_Two-PhCH_TwoCH_Two, 3-NO_Two-4-Me-PhCH_TwoCH_Two, 3-Me-4-NO_Two-PhCH_TwoCH_Two, 3-i-Pr-PhCH_TwoCH_Two, 4-i-Pr-PhCH_TwoCH_Two, 3,4- (i-Pr)_Two-PhCH_TwoCH_Two PhCH_TwoCH_TwoCH_Two, 2-F-PhCH_TwoCH_TwoCH_Two, ────────────────────────────────────

[0110]

[Table 32] {R-On-L-} ──────────────────────────────── 3-F-PhCH_TwoCH_TwoCH_Two, 4-F-PhCH_TwoCH_TwoCH_Two, 2-Cl-PhCH_TwoCH_TwoCH_Two, 3-Cl-PhCH_TwoCH_TwoCH_Two, 4-Cl-PhCH_TwoCH_TwoCH _Two , 2-Br-PhCH_TwoCH_TwoCH_Two, 3-Br-PhCH_TwoCH_TwoCH_Two, 4-Br-PhCH_TwoCH_TwoCH_Two, 2,4-F_Two-PhCH_TwoCH_TwoCH_Two, 3,4-F_Two-PhCH_TwoCH_TwoCH_Two, 2,4-Cl_Two-PhCH_TwoCH_TwoCH_Two, 3,4-Cl_Two-PhCH_TwoCH_TwoCH_Two, 3,4,5-F_Three-PhCH_TwoCH_TwoCH_Two, 3,4,5-Cl_Three-PhCH_TwoCH_TwoCH_Two, 2-F-4-Cl-PhCH_TwoCH_TwoCH_Two, 3-F-4-Cl-PhCH_TwoCH_TwoCH_Two , 3-Cl-4-F-PhCH_TwoCH_TwoCH_Two, 2-Cl-4-Br-PhCH_TwoCH_Two CH_Two, 3-Cl-4-Br-PhCH_TwoCH_TwoCH_Two, 3-Br-4-Cl-PhCH _Two CH_TwoCH_Two, 2-F-3-Cl-4-Cl-PhCH_TwoCH_TwoCH_Two, 3-Cl-4-Cl-5-F-PhCH_TwoCH_TwoCH_Two, 3-Cl-4-Cl-6-F-PhCH_TwoCH_TwoCH_Two 2-CF_Three-PhCH_TwoCH_TwoCH_Two, 3-CF_Three-PhCH_TwoCH_TwoCH_Two, 4-CF_Three− PhCH_TwoCH_TwoCH_Two 2,4 -− (CF_Three)_Two-PhCH_TwoCH_TwoCH_Two, 3,4- (CF_Three)_Two-PhCH_TwoCH_Two CH_Two 2-F-3-CF_Three-PhCH_TwoCH_TwoCH_Two, 3-CF_Three-4-F-PhCH_TwoCH_TwoCH_Two, 3-CF_Three-5-F-PhCH_TwoCH_TwoCH_Two, 3-CF_Three-6-F-PhCH_TwoCH_TwoCH_Two, 2-F-4-CF_Three-PhCH_TwoCH_TwoCH_Two, 3-F-4-CF_Three-PhCH_TwoCH_TwoCH_Two 3-CF_Three-4-Cl-PhCH_TwoCH_TwoCH_Two, 2-Cl-4-CF_Three-PhCH_TwoCH _Two CH_Two, 3-Cl-4-CF_Three-PhCH_TwoCH_TwoCH_Two ────────────────────────────────────

[0111]

[Table 33] {R-On-L-} ──────────────────────────────── 3-CF_Three-4-Br-PhCH_TwoCH_TwoCH_Two, 2-Br-4-CF_Three-PhCH_TwoCH _Two CH_Two, 3-Br-4-CF_Three-PhCH_TwoCH_TwoCH_Two 2-F-3-F-4-CF_Three-PhCH_TwoCH_TwoCH_Two, 3-F-4-F-5-CF_Three-P hCH_TwoCH_TwoCH_Two 2,3,5,6-F_Four−4-CF_Three-PhCH_TwoCH_TwoCH_Two 2-Me-PhCH_TwoCH_TwoCH_Two, 3-Me-PhCH_TwoCH_TwoCH_Two, 4-Me-P hCH_TwoCH_TwoCH_Two 2,4-Me_Two-PhCH_TwoCH_TwoCH_Two, 3,4-Me_Two-PhCH_TwoCH_TwoCH_Two, 3-Me-4-F-PhCH_TwoCH_TwoCH_Two, 2-F-4-Me-PhCH_TwoCH_TwoCH_Two, 3-F-4-Me-PhCH_TwoCH_TwoCH_Two, 3-Me-4-Cl-PhCH_TwoCH_TwoCH_Two, 2-Cl-4-Me-PhCH_TwoCH_Two CH_Two, 3-Cl-4-Me-PhCH_TwoCH_TwoCH_Two, 2-CF_ThreeO-PhCH_TwoCH_TwoCH_Two, 3-CF_ThreeO-PhCH_TwoCH_TwoCH_Two, 4-CF_ThreeO-PhCH_TwoCH_Two CH_Two 2,4 -− (CF_ThreeO)_Two-PhCH_TwoCH_TwoCH_Two, 3,4- (CF_ThreeO)_Two-PhCH_TwoCH_TwoCH_Two, 3-CF_ThreeO-4-F-PhCH_TwoCH_TwoCH_Two, 2-F-4-CF_ThreeO-PhCH_TwoCH _Two CH_Two, 3-F-4-CF_ThreeO-PhCH_TwoCH_TwoCH_Two, 3-CF_ThreeO-4-Cl-PhCH_TwoCH_TwoCH_Two, 2-Cl-4-CF_ThreeO-PhCH_Two CH_TwoCH_Two, 3-Cl-4-CF_ThreeO-PhCH_TwoCH_TwoCH_Two, 2-CN-PhCH_TwoCH_TwoCH_Two, 3-CN-PhCH_TwoCH_TwoCH_Two, 4-CN-P hCH_TwoCH_TwoCH_Two 2-NO_Two-4-Cl-PhCH_TwoCH_TwoCH_Two, ────────────────────────────────────

[0112]

[Table 34] {R-On-L-} ──────────────────────────────── 2,4- (NO ₂ ) ₂ -PhCH ₂ CH ₂ CH ₂ , 3 _{-NO 2 -4-Me-PhCH 2} CH 2 C H 2, 3-Me-4-NO 2 -PhCH 2 CH 2 CH 2, 3-i-Pr-PhCH 2 CH 2 CH 2, 4-i-Pr _{-PhCH 2 CH 2 CH 2, 3,4-} (i-Pr) 2 -PhCH 2 C H 2 CH 2, PhCH (Me) CH 2, 2-F-PhCH (Me) CH 2, 3-F-PhCH (Me) CH ₂ , 4-F-PhCH (Me) CH ₂ , 2-Cl-PhCH (Me) CH ₂ , 3-Cl-PhCH (Me) CH ₂ , 4-Cl-PhCH (Me) CH ₂ , 2-B r-PhCH ( Me) CH 2, 3-B _{-PhCH (Me) CH 2, 4} -Br-Ph CH (Me) CH 2, 2,4-F 2 -PhCH (Me) CH 2, 3,4-F 2 -PhCH (Me) CH 2, 2, _{4 -Cl 2 -PhCH (Me) CH} 2, 3,4-Cl 2 -PhCH (Me) CH 2, 3,4,5-F 3 -PhCH (Me) CH 2, 3,4,5-Cl 3 _{-PhCH (Me) C H 2,} 2-F-4-Cl-PhCH (Me) CH 2, 3-F-4-Cl-PhCH (Me) CH 2, 3-Cl-4-F-PhCH (Me _{) CH 2, 2-Cl-} 4-Br-PhCH (Me) CH 2, 3-Cl-4-Br-PhCH (Me) CH 2, 3-Br-4-Cl -PhCH (Me) CH 2, 2 -F-3-Cl-4- Cl-PhCH (Me) CH 2, 3-Cl-4-Cl-5-F -PhCH (Me) CH 2, 3-Cl-4-Cl-6-F-PhCH (Me _{) CH 2 2-CF 3 -PhCH} (Me) CH 2, 3-CF 3 -PhCH (Me) CH 2, 4-C F 3 -PhCH (Me) CH 2 2,4- (CF 3) 2 -PhCH (Me) CH ₂ , ────────────────────────────────────

[0113]

[Table 35] {R-On-L-} ──────────────────────────────── 3,4 -− (CF_Three)_Two-PhCH (Me) CH_Two 2-F-3-CF_Three-PhCH (Me) CH_Two, 3-CF_Three-4-F-PhCH (Me) CH_Two, 3-CF_Three-5-F-PhCH (Me) CH_Two, 3-CF_Three-6-F-PhCH (Me) CH_Two, 2-F-4-CF_Three-PhCH (Me) CH_Two, 3-F-4-CF _Three -PhCH (Me) CH_Two 3-CF_Three-4-Cl-PhCH (Me) CH_Two, 2-Cl-4-CF_Three-PhCH (Me) CH_Two, 3-Cl-4-CF_Three-PhCH (Me) CH_Two 3-CF_Three-4-Br-PhCH (Me) CH_Two, 2-Br-4-CF_Three-PhCH (Me) CH_Two, 3-Br-4-CF_Three-PhCH (Me) CH_Two 2-F-3-F-4-CF_Three-PhCH (Me) CH_Two, 3-F-4-F-5-CF_Three-PhCH (Me) CH_Two 2,3,5,6-F_Four−4-CF_Three-PhCH (Me) CH_Two 2-Me-PhCH (Me) CH_Two, 3-Me-PhCH (Me) CH_Two, 4-Me-PhCH (Me) CH_Two 2,4-Me_Two-PhCH (Me) CH_Two, 3,4-Me_Two-PhCH (Me) CH_Two, 3-Me-4-F-PhCH (Me) CH_Two, 2-F-4-Me-PhCH (Me) CH_Two, 3-F-4-Me-PhCH (Me) CH_Two, 3-Me-4-Cl-PhCH (Me) CH_Two, 2-Cl-4-Me-PhCH (Me) CH_Two, 3-Cl-4-Me-PhCH (Me) CH_Two, 2-CF_ThreeO-PhCH (Me) CH_Two, 3-CF_ThreeO-PhCH (Me) CH_Two, 4-CF_ThreeO-PhCH (Me) CH_Two 2,4 -− (CF_ThreeO)_Two-PhCH (Me) CH_Two, 3,4- (CF_ThreeO)_Two-PhCH (Me) CH_Two, ────────────────────────────────────

[0114]

[Table 36] {R-On-L-} ──────────────────────────────── 3-CF_ThreeO-4-F-PhCH (Me) CH_Two, 2-F-4-CF_ThreeO-PhCH (Me) CH_Two, 3-F-4-CF_ThreeO-PhCH (Me) CH_Two, 3-CF_ThreeO-4-Cl-PhCH (Me) CH_Two, 2-Cl-4-CF_ThreeO-PhCH (Me) CH_Two, 3-Cl-4-CF_ThreeO-PhCH (Me) CH_Two, 2-CN-PhCH (Me) CH_Two, 3-CN-PhCH (Me) CH_Two, 4-CN-PhCH (Me) CH_Two 2-NO_Two-4-Cl-PhCH (Me) CH_Two, 2-NO_Two-4-NO_Two-PhCH (Me) CH_Two, 3-NO_Two-4-Me-PhCH (Me) CH_Two, 3-Me-4-NO_Two-PhCH (Me) CH_Two, 3-i-Pr-PhCH (Me) CH_2,4-i-Pr-PhCH (Me) CH_2,3,4- (i-Pr)_Two-PhCH (Me) CH_Two PhCH_TwoCH (Me), 2-F-PhCH_TwoCH (Me), 3-F-PhCH_TwoCH (Me), 4-F-PhCH_TwoCH (Me), 2-Cl-PhCH_TwoCH (Me), 3-Cl-PhCH_TwoCH (Me), 4-Cl-PhCH_TwoCH (Me), 2-Br-PhCH_TwoCH (Me), 3-Br-PhCH_TwoCH (Me), 4-Br-Ph CH_TwoCH (Me), 2,4-F_Two-PhCH_TwoCH (Me), 3,4-F_Two-PhCH _Two CH (Me), 2,4-Cl_Two-PhCH_TwoCH (Me), 3,4-Cl_Two-PhCH _Two CH (Me), 3,4,5-F_Three-PhCH_TwoCH (Me), 3,4,5-Cl_Three-Ph CH_TwoCH (Me), 2-F-4-Cl-PhCH_TwoCH (Me), 3-F-4-Cl-PhCH_TwoCH (Me), 3-Cl-4-F-PhCH_TwoCH (Me), 2-Cl-4-Br-PhCH_Two CH (Me), 3-Cl-4-Br-PhCH_TwoCH (Me), 3-Br-4-Cl-PhCH_TwoCH (Me), ────────────────────────────────────

[0115]

[Table 37] {R-On-L-} ──────────────────────────────── 2-F-3-Cl-4-Cl-PhCH_TwoCH (Me), 3-Cl-4-Cl-5-F-PhCH_TwoCH (Me), 3-Cl-4-Cl-6-F-PhCH_TwoCH (Me), 2-CF_Three-PhCH_TwoCH (Me), 3-CF_Three-PhCH_TwoCH (Me), 4-CF_Three-PhCH_TwoCH (Me), 2,4- (CF_Three)_Two-PhCH_TwoCH (Me), 3,4- (CF_Three)_Two-PhCH_TwoCH (Me), 2-F-3-CF_Three-PhCH_TwoCH (Me), 3-CF_Three-4-F-PhCH_TwoCH (Me), 3-CF_Three-5-F-PhCH_TwoCH (Me), 3-CF_Three-6-F-PhCH_TwoCH (Me), 2-F-4-CF_Three-PhCH_TwoCH (Me), 3-F-4-CF _Three -PhCH_TwoCH (Me), 3-CF_Three-4-Cl-PhCH_TwoCH (Me), 2-Cl-4-CF_Three-PhCH_TwoCH (Me), 3-Cl-4-CF_Three-PhCH_TwoCH (Me), 3-CF_Three-4-Br-PhCH_TwoCH (Me), 2-Br-4-CF_Three-PhCH_TwoCH (Me), 3-Br-4-CF_Three-PhCH_TwoCH (Me), 2-F-3-F-4-CF_Three-PhCH_TwoCH (Me), 3-F-4-F-5-CF_Three− PhCH_TwoCH (Me), 2, 3, 5, 6-F_Four−4-CF_Three-PhCH_TwoCH (Me), 2-Me-PhCH_TwoCH (Me), 3-Me-PhCH_TwoCH (Me), 4-Me-PhCH_TwoCH (Me), 2,4-Me_Two-PhCH_TwoCH (Me), 3,4-Me_Two-PhCH_TwoCH (Me), 3-Me-4-F-PhCH_TwoCH (Me), 2-F-4-Me-PhCH_TwoCH (Me), 3-F-4-Me-PhCH_TwoCH (Me), 3-Me-4-Cl-PhCH_TwoCH (Me), ────────────────────────────────────

[0116]

[Table 38] {R-On-L-} ──────────────────────────────── 2-Cl-4-Me-PhCH ₂ CH (Me), 3-Cl _{-4-Me-PhCH 2 CH (} Me), 2-CF 3 O-PhCH 2 CH (Me), 3-CF 3 O-PhCH 2 CH (Me), 4 -CF 3 O-PhCH 2 CH (Me) _{, 2,4- (CF 3 O) 2} -PhCH 2 CH (Me), 3,4- (CF 3 O) 2 -PhCH 2 CH (Me), 3-CF 3 O-4-F-PhCH 2 CH (Me), 2-F- 4-CF 3 O-PhCH 2 C H (Me), 3-F-4-CF 3 O-PhCH 2 CH (Me), 3-CF 3 O-4-Cl-PhCH _{2 CH (Me), 2-} Cl-4-CF 3 O-PhC H 2 H (Me), 3-Cl -4-CF 3 O-PhCH 2 CH (Me), 2-CN-PhCH 2 CH (Me), 3-CN-PhCH 2 CH (Me), 4-CN -PhCH 2 CH (Me), 2-NO 2 -4-Cl-PhCH 2 CH (Me), 2-NO 2 -4-NO 2 -PhCH 2 CH (Me), 3-NO 2 -4-Me-PhCH 2 CH (Me), 3-Me- 4-N O 2 -PhCH 2 CH (Me), 3-i-Pr-PhCH 2 CH (Me), 4-i- Pr-PhCH 2 CH (Me), 3,4 _{- (i-Pr) 2 -PhCH} 2 CH (Me), PhCH 2 C (Me) 2, 2-F-PhCH 2 C (Me) 2, 3-F-PhCH 2 C (Me) 2, 4-F _{-PhCH 2 C (Me) 2,} 2-Cl-PhCH 2 C (Me) 2, 3- Cl-PhCH 2 C (Me) 2, 4-Cl-PhCH 2 C (Me _{2, 2-Br-Ph CH} 2 C (Me) 2, 3-Br-PhCH 2 C (Me) 2, 4-Br-PhCH 2 C (Me) 2, 2,4-F 2 -PhCH 2 C ( _{Me) 2, 3,4-F 2} -PhCH 2 C (Me) 2, ─────────────────────────────── ─────

[0117]

[Table 39] {R-On-L-} _{──────────────────────────────── 2,4-Cl 2 -PhCH 2 C} (Me) 2, 3,4 _{-Cl 2 -PhCH 2 C (Me)} 2, 3,4,5-F 3 -PhCH 2 C (Me) 2, 3,4,5-Cl 3 -PhCH 2 C (Me) 2, 2-F- 4-Cl-PhCH ₂ C (Me) ₂ , 3-F-4-Cl-PhCH ₂ C (Me) ₂ , 3-Cl-4-F-PhCH ₂ C (Me) ₂ , 2-Cl-4- _{Br-PhCH 2 C (Me)} 2, 3-Cl-4-Br-Ph CH 2 C (Me) 2, 3-Br-4-Cl-PhCH 2 C (Me) 2, 2-F-3-Cl _{-4-Cl-PhCH 2 C (} Me) 2, 3-Cl-4-Cl-5-F- PhCH 2 C (Me) 2, 3 -Cl-4-Cl-6- F-PhCH 2 C (Me) 2 2-CF 3 -PhCH 2 C (Me) 2, 3-CF 3 -PhCH 2 C (Me) 2, 4-CF 3 -PhCH ₂ C (Me) ₂ , 2,4- (CF ₃ ) ₂ -PhCH ₂ C (Me) ₂ , 3,4- (CF ₃ ) ₂ -PhCH ₂ C (Me) ₂ 2 -F-3-CF _{3 -PhCH 2 C (Me) 2,} 3-CF 3 -4-F-PhCH 2 C (M e) 2, 3-CF 3 -5-F-PhCH 2 C (Me) 2, 3-CF 3 -6 _{-F-PhCH 2 C (Me)} 2, 2-F-4-CF 3 -PhCH 2 C (Me) 2, 3-F-4-CF 3 -P hCH 2 C (Me) 2 3-CF 3 - _{4-Cl-PhCH 2 C (} Me) 2, 2-Cl-4-CF 3 -PhCH 2 C (Me) 2, 3-Cl-4-CF 3 -PhCH 2 C (Me) 2 3-CF 3 - _{4-Br-PhCH 2 C (} Me) 2, 2-Br-4 _{CF 3 -PhCH 2 C (Me)} 2, 3-Br-4-CF 3 -PhCH 2 C (Me) 2 2-F-3-F-4-CF 3 -PhCH 2 C (Me) 2, 3- F-4-F-5- CF 3 -P hCH 2 C (Me) 2 2,3,5,6-F 4 -4-CF 3 -PhCH 2 C (Me) 2 ──────── ────────────────────────────

[0118]

[Table 40] {R-On-L-} ──────────────────────────────── 2-Me-PhCH_TwoC (Me)_Two, 3-Me-PhCH_TwoC (Me)_Two, 4-Me-PhCH_TwoC (Me)_Two 2,4-Me_Two-PhCH_TwoC (Me)_Two, 3,4-Me_Two-PhCH_TwoC (Me)_Two, 3-Me-4-F-PhCH_TwoC (Me)_Two, 2-F-4-Me-PhCH_TwoC (Me)_Two, 3-F-4-Me-PhCH_TwoC (Me)_Two, 3-Me-4-Cl-PhCH_TwoC (Me)_Two, 2-Cl-4-Me-PhCH_TwoC (Me)_Two, 3-Cl-4-Me-PhCH_TwoC (Me)_Two, 2-CF_ThreeO-PhCH_TwoC (Me)_Two, 3-CF_ThreeO-PhCH_TwoC (Me)_Two, 4-CF_ThreeO-PhCH_TwoC (Me)_Two 2,4 -− (CF_ThreeO)_Two-PhCH_TwoC (Me)_Two, 3,4- (CF_ThreeO)_Two-PhCH_Two C (Me)_Two, 3-CF_ThreeO-4-F-PhCH_TwoC (Me)_Two, 2-F-4-CF_ThreeO-PhCH_TwoC (Me)_Two, 3-F-4-CF_ThreeO-PhCH_TwoC (Me)_Two, 3-CF_ThreeO-4-Cl-PhCH_TwoC (Me)_Two, 2-Cl-4-CF_ThreeO-PhCH _Two C (Me)_Two, 3-Cl-4-CF_ThreeO-PhCH_TwoC (Me)_Two, 2-CN-PhCH_TwoC (Me)_Two, 3-CN-PhCH_TwoC (Me)_Two, 4-CN-PhCH_TwoC (Me)_Two 2-NO_Two-4-Cl-PhCH_TwoC (Me)_Two, 2-NO_Two-4-NO_Two-PhCH_Two C (Me)_Two, 3-NO_Two-4-Me-PhCH_TwoC (Me)_Two, 3-Me-4-NO_Two -PhCH_TwoC (Me)_Two, 3-i-Pr-PhCH_TwoC (Me)_Two, 4-i-Pr-PhCH_TwoC (Me)_Two, 3,4- (i-Pr)_Two-PhCH_TwoC (Me)_Two ────────────────────────────────────

[0119]

[Table 41] {R-On-L-} ──────────────────────────────── PhCH (COOMe), 2-F-PhCH (COOMe), 3-F- PhCH (COOMe), 4-F-PhCH (COOMe), 2-Cl-PhCH (COOMe), 3-Cl-PhCH (COOMe), 4-Cl-PhCH (COOMe), 2-Br-PhCH (COOMe) , 3-B r-PhCH ( COOMe), 4-Br-PhCH (COOMe), 2,4-F 2 -PhCH (COOMe), 3,4-F 2 -PhCH (COOMe), 2, 4-Cl 2 -PhCH (COOMe), 3,4-Cl 2 -PhCH (COOMe), 3,4,5-F 3 -PhCH (COOM _{), 3,4,5-Cl 3 -PhCH (} COOM e), 2-F-4-Cl-PhCH (COOMe), 3-F-4-Cl-PhCH (COO Me), 3-Cl-4- F-PhCH (COOMe), 2-Cl-4-Br-PhCH (COOMe), 3-Cl-4-Br-PhCH (COOMe), 3-Br-4-Cl-PhCH (COOMe), 2-F -3-Cl-4-Cl-PhCH (COOMe), 3-Cl-4-Cl-5-F-PhCH (COOMe), 3-Cl-4-Cl-6-F-PhCH (COOMe), _{2-CF 3 -PhCH (COOMe)} , 3-CF 3 -PhCH (COOMe), 4- CF 3 -PhCH (COOMe), 2,4- (CF 3) 2 -PhCH (COOMe), 3,4- ( _{CF 3) 2 -PhCH (C OOMe} ) 2-F-3-CF 3 -PhCH (COOMe) _{, 3-CF 3 -4-F} -PhCH (CO OMe), 3-CF 3 -5-F-PhCH (COOMe), 3-CF 3 -6-F-Ph CH (COOMe), 2-F-4 —CF ₃ —PhCH (COOMe), 3-F-4-CF ₃ —PhCH (COOMe), ─────────────────────────── ─────────

[0120]

[Table 42] {R-On-L-} ──────────────────────────────── 3-CF ₃ -4-Cl-PhCH (COOMe), 2-Cl- _{4-CF 3 -PhCH (COOMe)} , 3-Cl-4-CF 3 -PhCH (COOMe), 3-CF 3 -4-Br-PhCH (COOMe), 2-Br-4-CF 3 -PhCH (COOMe ), 3-Br-4- CF 3 -PhCH (COOMe), 2-F-3-F-4-CF 3 -PhCH (COOMe), 3-F-4-F-5-CF 3 - PhCH (COOMe _{), 2,3,5,6-F 4 -4-} CF 3 -PhCH (COOMe), 2-Me-PhCH (COOMe), 3-Me-PhCH (COOMe), 4-M e-PhCH _{(COOMe), 2,4-Me 2} -PhCH (COOMe), 3,4- Me 2 -PhCH (COOMe), 3-Me-4-F-PhCH (COOMe), 2-F-4-Me-PhCH (COOMe), 3-F-4-Me-PhCH (COOMe), 3-Me-4-Cl-PhCH (COOMe), 2-Cl-4-Me-PhCH (COOMe), 3-Cl-4 -Me-PhCH (COOMe), 2 -CF 3 O-PhCH (COOMe), 3-CF 3 O-PhCH (COOMe), 4-CF 3 O-PhCH (COOMe), 2,4- (CF 3 O) _{2 -PhCH (COOMe), 3,4- (} CF 3 O) 2 -PhCH (COOMe), 3-CF 3 O-4-F-PhCH (COOMe), 2-F-4-CF 3 O-PhCHC OOMe ), 3-F-4- CF 3 O-PhCH (COOMe) _{, 3-CF 3 O-4} -Cl-PhCH (COOMe), 2-Cl-4-CF 3 O-PhC H (COOMe), 3-Cl-4-CF 3 O-PhCH (COOMe), 2-CN -PhCH (COOMe), 3-CN-PhCH (COOMe), ─────────────────────────────────── ─

[0121]

[Table 43] {R-On-L-} ──────────────────────────────── 4-CN-PhCH (COOMe), 2-NO ₂ -4-Cl- PhCH (COOMe), 2-NO 2 -4-NO 2 -PhCH (COOMe), 3-NO 2 -4-Me-PhCH (COOMe), 3-Me-4- NO 2 -PhCH (COOMe), 3- i-Pr-PhCH (COOMe) , 4- i-Pr-PhCH (COOMe), 3,4- (i-Pr) 2 -PhCH (COOMe), PhCH 2 CH (COOMe), 2-F-PhCH 2 CH (COOMe), 3-F- PhCH 2 CH (COOMe), 4-F-PhCH 2 CH (COOMe), 2-Cl -PhCH 2 CH (COOMe), 3-Cl- PhCH 2 CH (COOMe), 4- Cl-PhCH 2 CH (COOMe), 2-Br-PhCH 2 CH (COOMe), 3-Br-PhCH 2 CH (COOMe), 4- _{br-PhCH 2 CH (COOMe)} , 2,4-F 2 -PhCH 2 CH (COOMe), 3,4-F 2 -PhCH 2 CH (COO Me), 2,4-Cl 2 -PhCH 2 CH (COOMe _{), 3,4-Cl 2 -PhCH 2} CH (COOMe), 3,4,5-F 3 -PhCH 2 CH (COOMe), 3,4,5-Cl 3 -PhCH 2 CH (COOMe), 2- _{F-4-Cl-PhCH 2} CH (COOMe), 3-F-4- Cl-PhCH 2 CH (COOMe), 3-Cl-4-F-PhCH 2 CH (COO Me), 2-Cl-4- _{br-PhCH 2 CH (COOMe)} , 3-Cl- _{4-Br -PhCH 2 CH (COOMe} ), 3-Br-4-Cl-PhCH 2 CH (COOM e), 2-F-3-Cl-4-Cl-PhCH 2 CH (COOMe), 3-Cl- 4- Cl-5-F-PhCH 2 CH (COOMe), 3-Cl-4-Cl-6-F-Ph CH 2 CH (COOMe), ─────────────── ─────────────────────

[0122]

[Table 44] {R-On-L-} ──────────────────────────────── 2-CF ₃ -PhCH ₂ CH (COOMe), 3-CF ₃ -PhCH _{2 CH (COOM e), 4} -CF 3 -PhCH 2 CH (COOMe), 2,4- (CF 3) 2 -PhCH 2 CH (COOMe), 3,4- (CF 3) 2 -PhC H 2 CH (COOMe) 2-F-3 -CF 3 -PhCH 2 CH (COOMe), 3-CF 3 -4-F-PhCH 2 CH (COOMe), 3-CF 3 -5-F-PhCH 2 CH (COOMe) _{, 3-C F 3 -6-} F-PhCH 2 CH (COOMe), 2-F-4-CF 3 -PhCH 2 CH (COOMe), 3-F-4-CF 3 -PhCH 2 CH (C _{OMe), 3-CF 3 -4} -Cl-PhCH 2 CH (COOMe), 2-Cl-4-CF 3 -Ph CH 2 CH (COOMe), 3-Cl-4-CF 3 -PhCH 2 CH (COOMe _{), 3-CF 3 -4-} Br-PhCH 2 CH (COOMe), 2-Br-4-CF 3 -Ph CH 2 CH (COOMe), 3-Br-4-CF 3 -PhCH 2 CH (COOMe) , 2-F-3-F -4-CF 3 -PhCH 2 CH (COOMe), 3-F-4-F-5-C F 3 -PhCH 2 CH (COOMe), 2,3,5,6- tetra _{-F-4-CF 3 -PhCH 2} CH (COOMe), 2-Me-PhCH 2 CH (COOMe), 3-Me-PhCH 2 CH (COOM e), 4-Me-PhCH 2 CH (COOMe), _{2,4-Me 2 -PhCH 2 CH (} COOMe), 3,4-Me 2 -Ph _{H 2 CH (C OOMe),} ────────────────────────────────────

[0123]

[Table 45] {R-On-L-} ──────────────────────────────── 3-Me-4-F-PhCH_TwoCH (COOMe), 2-F-4-Me-PhCH_TwoCH (COOMe), 3-F-4-Me-PhCH_TwoCH (COOMe), 3-Me-4-Cl-PhCH_TwoCH (COOMe), 2-Cl-4-Me-PhCH_TwoCH (COOMe), 3-Cl-4-Me-PhCH_TwoCH (COOMe), 2-CF_ThreeO-PhCH_TwoCH (COOMe), 3-CF_ThreeO-PhCH_TwoCH (CO OMe), 4-CF_ThreeO-PhCH_TwoCH (COOMe), 2,4- (CF_ThreeO)_Two-PhCH_TwoCH (COOMe), 3,4- (CF_ThreeO)_Two-P hCH_TwoCH (COOMe), 3-CF_ThreeO-4-F-PhCH_TwoCH (COOMe), 2-F-4-CF_ThreeO-Ph CH_TwoCH (COOMe), 3-F-4-CF_ThreeO-PhCH_TwoCH (COOMe), 3-CF_ThreeO-4-Cl-PhCH_TwoCH (COOMe), 2-Cl-4-CF_ThreeO-PhCH_TwoCH (COOMe), 3-Cl-4-CF_ThreeO-PhCH_TwoCH (COO Me), 2-CN-PhCH_TwoCH (COOMe), 3-CN-PhCH_TwoCH (COOMe), 4-CN-PhCH_TwoCH (COOMe), 2-NO_Two-4-Cl-PhCH_TwoCH (COOMe), 2,4- (NO_Two)_Two-PhCH _Two CH (COOMe), 3-NO_Two-4-Me-PhCH_TwoCH (COOMe), 3-Me-4-NO_Two-PhCH_TwoCH (COOMe), 3-i-Pr-PhCH_TwoCH (COOMe), 4-i-Pr-PhCH_TwoCH (COOMe), 3,4- (i-Pr)_Two-PhCH_TwoCH (COOMe), ────────────────────────────────────

[Table-7]

[0125]

Embedded image

[0126]

Embedded image

[0127]

[Table 46] ──────────────────────────────────── R¹ メ チ ル Methyl, ethyl, normal propyl, isopropyl, cyclo Propyl group, normal butyl group, isobutyl group, cyclobutyl group, secondary butyl group, normal pentyl group, cyclopentyl group, normal hexyl group, cyclohexyl group, PhCH_Two, 2-F-PhCH_Two, 3-F-PhCH_Two, 4-F-PhCH_Two, 2-Cl-PhCH_Two, 3-Cl-PhCH_Two, 4-Cl-PhCH_Two, 2-Br-PhCH_Two , 3-Br-PhCH_Two, 4-Br-PhCH_Two, 2-Me-PhCH_Two, 3-Me-PhCH_Two, 4-Me-PhCH_Two, 2-MeO-PhCH_Two, 3-MeO-PhCH _Two , 4-MeO-PhCH_Two, 2-CF_Three-PhCH_Two, 3-CF_Three-PhCH_Two, 4-CF_Three-PhCH_Two, 2-CF_ThreeO-PhCH_Two, 3-CF_ThreeO-PhCH_Two, 4-CF_Three0-PhCH_Two, 2-MeS-PhCH_Two, 3-MeS-PhCH_Two, 4-MeS-Ph CH_Two, 2-MeSO_Two-PhCH_Two, 3-MeSO_Two-PhCH_Two, 4-MeSO_Two− PhCH_Two, 2-MeNH-PhCH_Two, 3-MeNH-PhCH_Two, 4-MeNH-PhCH_Two, 2- (COOMe) -PhCH_Two, 3- (COOMe) -PhCH_Two, 4- (COOMe) -PhCH_Two, 2- (COOEt) -PhCH_Two, 3- (COOEt) -PhCH_Two, 4- (COOEt) -PhCH_Two, 2-NO_Two-PhCH_Two, 3-NO_Two-PhCH_Two, 4-NO_Two-PhCH_Two, 2-CN-PhCH_Two, 3-CN-Ph CH_Two, 4-CN-PhCH_Two, Trifluoromethyl group, pentafluoroethyl group, heptafluoronormal propyl group, chlorodifluoromethyl group and bromodifluoromethyl group ───────────── In the table, Me represents a methyl group, Et represents an ethyl group, i-Pr represents an isopropyl group, and Ph represents a phenyl group.

In applying the compound of the present invention as a herbicide, generally, a suitable carrier, for example, a solid carrier such as clay, talc, bentonite, urea, ammonium sulfate, walnut powder, diatomaceous earth, white carbon, or water, alcohols (isopropanol) , Butanol, ethylene glycol, benzyl alcohol, furfuryl alcohol, etc.), aromatic hydrocarbons (toluene, xylene, methylnaphthalene, etc.), ethers (anisole, etc.), vegetable oils (soybean oil, cottonseed oil, etc.), ketones (cyclohexanone) , Isophorone, etc.), esters (butyl acetate, etc.), acid amides (N-methylpyrrolidone, etc.), and halogenated hydrocarbons (chlorobenzene, etc.). Activator, emulsifier, dispersant, penetrant Spreading agents, thickening agents, anti-freezing agents, anti-caking agent, was added stabilizers and the like, solutions, emulsions,
It can be put to practical use in any dosage form such as wettable powders, dry flowables, flowables, powders, granules and the like.

The compound of the present invention may be added to other herbicides, various insecticides, acaricides, nematicides, fungicides, plant growth regulators, synergists, fertilizers or the like at the time of preparation or spraying as required. You may mix and apply with a soil improving agent etc. In particular, by mixing and applying other pesticides, the cost can be reduced by reducing the amount of applied medicine, the spectrum can be expanded by the synergistic action of the mixed medicine,
A higher herbicidal effect can be expected. At this time, a combination with a plurality of known agricultural chemicals is possible at the same time. Examples of the kind of pesticide used in combination with the compound of the present invention include, for example,
Chemicals Handbook (Farm Chemica
ls Handbook) 1997 edition.

The amount of the applied compound of the present invention may vary depending on the application scene, application time, application method, weather conditions, preparation form, soil conditions, cultivated crops, etc., but generally, the amount of the active ingredient is 0.1 per hectare (ha). About 0001-20kg,
Preferably about 0.001 to 10 kg is appropriate. Next, a formulation example of a preparation when the compound of the present invention is used is specifically shown. However, the composition examples of the present invention are not limited to these. In the following formulation examples, "parts" means parts by weight.

[Wettable powder] Compound of the present invention {0.1-80 parts Solid carrier {10-90 parts Surfactant} 1 to 10 parts Others # 1 to 5 parts Others include, for example, an anti-caking agent.

[Emulsion] Compound of the present invention (0.1 to 30 parts) Liquid carrier (30 to 95 parts) Surfactant (5) To 15 parts [Flowable agent] Compound of the present invention 0.1 to 70 parts Liquid carrier 15 to 65 parts Surfactant 5 １２12 parts Others ────────5-30 parts Others include, for example, an antifreezing agent and a thickener.

[Granular wettable powder (dry flowable)] Compound of the present invention {0.1 to 90 parts Solid carrier {10 to 70 parts Surfactant} {1 to 20 parts [granule] Compound of the present invention} 0.0001 to 10 parts Solid carrier {90 to 99.99999 parts Others} 0.1 to 10 parts [Formulation Example 1] wettable powder of the present compound No. 3 50 parts Sieglite PFP 43 parts (Kaolin clay: trade name of Geek Light Industry Co., Ltd.) Solpol 5050 # 2 Part (anionic surfactant: Toho Chemical Industry Co., Ltd.) Lunox 1000C # 3 part (anionic surfactant: Toho Chemical Industry Co., Ltd.) Carplex # 80 ( Anti-caking agent) 2 parts (white carbon: trade name of Shionogi & Co., Ltd.) The above components are uniformly mixed and pulverized to obtain a wettable powder.

[Formulation Example 2] Emulsion Inventive compound No. 22───────3 parts Xylene ─────────76 parts Isophorone ─────────15 parts Solpol 3005X ────────6 parts (nonionic A mixture of a surfactant and an anionic surfactant: trade name of Toho Chemical Industry Co., Ltd.) The above are uniformly mixed to form an emulsion.

Formulation Example 3 Flowable Agent Compound No. 36 ──────35 parts Agrisol S-711 ───────8 parts (Nonionic surfactant: trade name of Kao Corporation) Lunox 1000C ────────0.5 Part (anionic surfactant: trade name of Toho Chemical Industry Co., Ltd.) 1% rhodopol water ─────────20 parts (thickener: trade name of Lone Poulin Co.) Ethylene glycol (antifreeze ) ───8 parts water ─────────28.5 parts The above are mixed uniformly to form a flowable agent.

[Formulation Example 4] Granular wettable powder (dry flowable agent) 10 # 75 parts Isoban No. 1 $ 10 parts (anionic surfactant: Kuraray Isoprene Chemical Co., Ltd.) Vanirex N $ 5 parts (anionic surfactant: Sanyo Kokusaku Pulp Co., Ltd.) Carplex # 80 ────────10 parts (white carbon: Shionogi & Co., Ltd. Co., Ltd.) The above components are uniformly mixed and pulverized to prepare a dry flowable agent.

[Formulation Example 5] Granules The present compound No. 12 ──────0.1 parts Bentonite ─────────50.0 parts Talc ─────────44.9 parts Toxanone GR-31A ─────── 5 parts (anionic surfactant: Sanyo Kasei Kogyo Co., Ltd.) After uniformly mixing and pulverizing the above, adding a small amount of water, stirring, mixing and kneading, granulating with an extrusion granulator, and drying. Into granules.

For use, the above-mentioned wettable powder, emulsion, flowable powder and granular wettable powder are diluted 50 to 1000 times with water so that the active ingredient is reduced to 0.000 per hectare (ha).
Spray to 1 to 10 kg. Next, the usefulness of the compound of the present invention as a herbicide will be specifically described in the following test examples. [Test Example 1] Herbicidal effect test by weed generation pretreatment under flooded conditions After placing alluvial soil in a 1/10000 arel Wagner pot, water was added and mixed to obtain a flooded condition at a depth of 4 cm. The above-mentioned pot is transplanted with rice at the 2 leaf stage, and the seeds of Nobie, Firefly, Konagi, Kikasigusa, Urikawa,
A tuber of Spodoptera mori was mixed and sowed. Pot at 25-30 ° C
The plants of the present invention were prepared according to the formulation examples so that the plants were grown in the greenhouse on the first day after the sowing, so that a predetermined dose was applied to the surface of the water. Three weeks after the treatment, the herbicidal effect on various weeds and the effect on rice were visually examined according to the following criteria. 0 is no effect and 5 is a 5-point scale showing complete withering. The results are shown in Table 8-1.

[0139] In each table, No. Is the compound No. described in the examples. And the symbols have the following meanings. A: nobie, B: firefly, C: scallop, D: stag beetle, E: urikawa, F: serrata, b: rice Criteria 5: Herbicidal rate 90% or more (almost completely withered) 4 ... Herbicidal rate 70% or more and 90% Less than 3: Herbicidal rate 40% or more and less than 70% 2: Herbicidal rate 20% or more and less than 40% 1: Herbicidal rate 5% or more and less than 20% 0 ... Herbicidal rate less than 5% (almost no effect) [Test Example 2] Flooding Test of weeding effect by weed post-treatment under conditions: After placing alluvial soil in a 1/1000 arel Wagner pot, water is added and mixed to obtain a flooding condition at a depth of 4 cm. Seeds of nobies, fireflies, pearls, and red stag beetles were mixed into the above pots. The pot was grown in a greenhouse at 25 to 30 ° C., and on the 14th day after sowing, the compound of the present invention prepared according to the formulation example was treated so as to have a predetermined dose on the water surface. Three weeks after the treatment, the herbicidal effect on various weeds was visually inspected according to the criteria of Test Example 1. The results are shown in Table 8-2. Note that N in each table
o. Is the compound No. described in the examples. And the symbols have the following meanings. A: Nobie, B: Firefly, C: Onagi, D: Kikashigusa [Test Example 3] Herbicidal effect test by soil treatment Put sterilized flood soil in a plastic box having a length of 33 cm, a width of 33 cm and a depth of 8 cm. Enokorogosa, oats, blackgrass, ichibi, onamomi,
The present invention prepared according to a blending example so as to have a predetermined dosage after mixing seeds of Aobuyu, Morning Glory, Ooinufufuguri, Hakobe, Rice, Maize, Wheat, Soybean, Cotton, Beet and covering about 1.5 cm, so as to have a predetermined dosage. The compound was evenly sprayed on the soil surface. Three weeks after the application of the chemical solution, the herbicidal effect on various weeds and the effect on crops were visually inspected in accordance with the criteria of Test Example-1. Table 8 shows the results.
-3. In addition, No. in each table. Is the compound No. described in the examples. And the symbols have the following meanings. G: Nobie, H: Enokorogosa, I: Oats, J:
Blackgrass, K: Ichibai, L: Onami-momi, M: Aoyama, N: Asagao, O: Oyanofuguri, P: Hakobe, a: Maize, b: Rice, c: Soybean, d: Cotton, e: Wheat, f: Beat [Test Example 4] Herbicidal effect test by foliage treatment Put sterilized flooded soil in a plastic box having a length of 33 cm, a width of 33 cm, and a depth of 8 cm, and add nobies, enokorogusa, oats, blackgrass, strawberries, onamimi,
Mixed seeds of Aobuyu, Morning Glory, Ooinufuguri, Chickweed, Rice, Maize, Wheat, Soybean, Cotton, Beetroot, cover about 1.5 cm, then grow the plants at room temperature of 25 to 30 ° C for 14 days, The compound of the present invention prepared according to the formulation example was uniformly applied to the foliage. Test Example 1 on herbicidal effects on various weeds and effects on crops 3 weeks after spraying the chemical solution
Was visually inspected according to the criteria of the above. Table 8-4 shows the results.
Shown in In addition, No. in each table. Is the compound No. described in the examples. And the symbols have the following meanings. G: Nobie, H: Enokorogosa, I: Oats, J:
Blackgrass, K: Ichibai, L: Onami-momi, M: Aoyama, N: Asagao, O: Oyanofuguri, P: Hakobe, a: Maize, b: Rice, c: Soybean, d: Cotton, e: Wheat, f: Beat

[Table 8-1]

[0141]

[Table 47] 化合物 Compound No. Drug dose g / a ABCDEF b ──────────────────────────────────── 4 10 0 0 0 3 0 0 0 5 10 5 5 5 5 0 0 0 9 10 4 0 4 4--0 10 10 5 3 5 5-0 0 11 10 4 3 5 4--0 12 10 2 0 3 5-0 0 17 10 4 3 5 5 2 0 0 19 10 5 0 5 5 0 0 0 26 10 3 0 0 2 0 0 0 27 10 3 0 0 5 0 0 0 28 10 2 0 2 5 0 0 0 34 10 2 0 0 0 2 0 0 35 10 0 0 0 4 0 0 0 36 10 5 4 4 5 2 0 0 38 10 0 0 0 2 0 0 0 39 10 4 0 4 4 0 0 0 40 10 0 0 3 2 5 0 0 41 10 0 0 4 5 0 0 0 42 10 5 5 5 2 0 0 0 50 10 2 0 0 0 0 0 0 54 10 3 2 5 5-0 0 55 10 0 3 3 4-0 0 56 10 0 0 2 5--0 ─────── ─────────────────────────────

[0142]

[Table 48] ──────────────────────────────────── Compound No. Dose g / a ABCDEF b ──────────────────────────────────── 57 10 0 0 1 2-0 0 58 10 0 1 2 3--0 59 10 5 2 5 0-4 0 60 10 0 5 5 2-0 0 ──────────────────────────── ────────

[Table 8-2]

[0144]

[Table 49] 化合物 Compound No. Positive dose g / a ABCD ─ ─────────────────────────────────── 3 10 0 2 3 5 4 10 1 0 0 0 6 10 3 4 2 0 9 10 3 0 4 4 10 10 2 0 5 5 12 10 3 0 5 5 17 10 0 4 5 3 18 10 3 3 5 5 19 10 0 3 5 5 22 10 3 0 0 5 25 10 0 0 0 5 27 10 2 4 3 5 28 10 3 0 0 5 29 10 3 0 0 4 33 10 2 3 2 3 35 10 2 3 3 5 36 10 0 4 2 5 37 10 2 2 1 5 38 10 2 3 2 5 39 10 2 2 3 5 40 10 0 0 4 5 41 10 0 1 5 5 ───────────────────────────────── ───

[0145]

[Table 50] ──────────────────────────────────── Compound No. Dose g / a ABCD ─ ─────────────────────────────────── 49 10 0 0 0 3 50 10 0 0-3 53 10 0 0 3 0 55 10 3 2 5 4 56 10 2 5 5 4 57 10 0 0 0 3 59 10 1 0 0 5 ─────────────────────── ─────────────

[Table 8-3]

[0147]

[Table 51] 化合物 Compound No. Drug dose g / a GHIJKLMNOP abcdef ──────────────────────────────────── 1 25 4 1 0 0 0 0-0 0 0 0- 0 0 0 0 2 25 0 0 0 0 0 0 0 0 4 0 0-0 0 0 0 6 25 1 1 0 0 0 0 0-0 0 0 0 0 0 0 0 7 25 0 1 0 0 0 0 0 0 0 0 0 0 0 0 0 0 10 25 0 0 0 0 0 0 0 0 2 2 0 0 0 0 0 2 11 25 0 0 0 0 0 0 0 0 0 3 0 0 0 0 0 2 12 25 0 0 0 0 0 0 4 0 2 5 0 0 0 0 0 5 18 25 3 2 4 5 0 0 0 0 5 5 1 0 0 0 1 5 19 25 0 0 0 0 0 0 0 0 1 3 0 0 0 0 0 0 27 25 0 0 0 0 0 0 1 0 3 3 0 0 0 0 0 0 28 25 1 0 0 0 0 0 5 0 5 5 0 0 0 0 0 4 29 25 0 0 0 1 0 0 0 0 2 1 0 0 0 0 0 0 36 25 0 1 0 0 0 0 0 0 2 2 0 0 0 0 0 0 37 25 0 0 0 4 0 0 0 0 1 1 0 0 0 0 0 0 38 25 0 0 0 0 0 0 0 0 0 1 0 0 0 0 0 0 39 25 0 0 0 0 0 0 4 0 4 4 0 0 0 0 0 1 41 25 0 0 0 0 0 0 1 0 0 0 0 0 0 0 0 0 42 25 3 4 0 0 3 0 4 0 0 3 0 0 0 0 0 5 43 25 2 3 0 0 0 0 3 0 0 0 0 0 0 0 0 0 49 25 0 0 0 0 0 0 2 0 4 4 0 0 0 0 0 5 53 25 0 0 0 0 0 0 5 0 0 0 0 0 0 0 0 0 55 25 0 0 0 4 0 0 0 0 3 3 0 0 0 0 0 0 58 25 0 0 0 0 0 3 0 0 0 0 0 0 0 0 0 0 ───────────────────────── ───────────

[Table 8-4]

[0149]

[Table 52] 化合物 Compound No. Drug dose g / a GHIJKLMNOP abcdef ──────────────────────────────────── 1 25 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0 3 25 5 5 5 5 5 5 5 5 5 5 0 2 1 2 0 5 8 25 0 0 0 0 0 0 0 0 1 1 0 0 0 0 0 0 9 25 0 0 2 2 5 1 0 5 5 5 0 0 0 0 0 5 10 25 3 3 2 4 5 5 5 5 5 5 0 0 2 1 0 5 11 25 2 2 2 2 2 1 1 4 5 5 0 0 0 0 0 5 12 25 5 5 5 5 5 5 5 5 5 5 0 1 4 5 0 5 18 25 3 5 5 5 5 5 5 5 5 5 0 0 1 4 1 5 19 25 1 1 1 3 2 4 5 5 5 5 0 0 1 0 0 5 20 25 0 0 0 0 0 0 0 0 5 5 0 0 0 0 0 1 21 25 0 0 0 0 0 0 0 0 1 1 0 0 0 0 0 0 22 25 0 0 1 4 5 5 5 5 5 5 0 0 0 0 0 5 24 25 0 0 1 0 0 0 0 0 0 5 0 0 0 0 0 0 25 25 0 0 3 4 5 4 5 4 5 5 0 0 0 0 0 5 26 25 0 0 2 0 2 4 5 4 5 5 0 0 0 0 0 2 27 25 0 0 0 0 4 3 5 5 5 5 0 0 0 0 0 5 28 25 0 0 5 3 1 5 5 3 5 5 0 0 0 0 0 5 29 25 0 0 0 0 0 0 5 0 5 5 0 0 0 0 0 5 33 25 0 0 0 0 0 0 0 0 5 5 0 0 0 0 0 1 34 25 0 0 0 2 3 2 4 5 5 5 0 0 0 0 0 5 35 25 0 0 2 2 4 2 5 3 5 5 0 0 0 0 0 5 ─────────── ─────────────────────────

[0150]

[Table 53] 化合物 Compound No. Drug dose g / a GHIJKLMNOP abcdef ──────────────────────────────────── 36 25 2 2 1 2 5 5 5 5 5 5 0 0 0 0 0 5 37 25 2 1 0 2 1---5 5 0 0 0 0 0 5 38 25 0 0 0 0 0 0 5 1 5 5 0 0 0 0 0 5 39 25 2 3 3 5 4 2 5 5 5 5 0 0 1 5 0 5 40 25 0 0 0 1 0 0 4 5 4 5 0 0 0 0 0 4 41 25 1 1 0 1 5 2 5 5 5 5 0 0 0 0 0 5 42 25 2 2 1- 0 1 5 0 5 5 0 0 0 0 0 5 43 25 2 3 0 0 1 5 5 0 5 3 0 0 0 0 0 1 46 25 0 0 0 1 0 0 0 0 4 5 0 0 0 0 0 1 48 25 0 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 49 25 4 1 0 5 4 3 5 5 5 5 0 0 1 0 0 5 50 25 0 0 1 2 2 4 5 4 5 5 0 0 0 0 0 5 51 25 2 1 0 0 2 1 2-1 1 0 0 0 0 0 0 52 25 0 0 1 0 2 1 3 4 5 5 0 0 0 0 0 5 53 25 0 0 0 0 4 1 3 2 5 3 0 0 0 0 0 0 54 25 1 1 1 0 0 0 4 3 5 5 0 0 0 0 0 1 55 25 0 3 1 0 5 1 5 5 5 5 0 0 0 0 0 5 56 25 0 0 0 0 3 1 5 5 2 5 0 0 0 1 0 5 57 25 0 0 1 1 3-5 5 5 5 0 0 0 4 0 5 58 25 0 0 0 0 5 0 5 2 5 5 0 0 0 0 0 5 59 25 0 0 1 2 3 0 5 0 4 5 0 0 0 0 0 5 60 25 4 5 0 0 0 0 0 0 0 0 0 0 0 0 0 0 61 25 0 0 0 0 0 0 0 0 4 3 0 0 0 0 0 0 ─────────────────────── ─────────────

────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. ⁶ Identification code FI C07D 405/12 231 C07D 405/12 231 409/12 231 409/12 231 (72) Inventor Chiaki Kawaguchi Shiraoka-cho, Minami-Saitama-gun, Saitama 1470 Shiraoka, Nissan Kagaku Kogyo Co., Ltd., Biological Science Research Institute (72) Inventor Tsutomu Naomaki 1470, Shirooka-cho, Shirooka-cho, Minami Saitama-gun, Saitama Prefecture Nissan Kagaku Kogyo Co., Ltd.

Claims (5)

[Claims] (1) Formula (I): [Wherein, R represents a hydrogen atom, a phenyl group optionally substituted with Qa, a pyridyl group optionally substituted with Qa, Qa
A furyl group which may be substituted with Qa, a thienyl group which may be substituted with Qa, a naphthyl group which may be substituted with Qa, or a 1,2-dioxymethylenephenyl group which may be substituted with Qa. represents, Qa is halogen atom, C ₁ -C ₄ alkyl group, a phenyl groups, C ₁ -C ₄ alkoxy groups, phenoxy groups, C ₁ -C ₄ haloalkyl groups, C ₁ -C ₄ haloalkoxy groups, C ₁ -C ₄ alkylthio, phenylthio, C ₁ -C ₄ alkylsulfonyl, C ₁ -C ₄ haloalkylthio, C ₁ -C ₄ alkylamino, di (C ₁ -C ₄ alkyl) amino, C ₁
-C ₄ alkoxycarbonyl group, a phenoxycarbonyl group, amide group, C ₁ -C ₄ alkylamido group, a phenyl amide group, a di (C ₁ -C ₄ alkyl) amido group, a nitro group,
Represents one or more substituents selected from a cyano group, a hydroxy group, an acetyloxy group and a benzoyloxy group, wherein R ¹ is a C ₁ -C ₆ alkyl group, a C ₃ -C ₆ cycloalkyl group, a C ₁ -C ₆ haloalkyl Groups, C ₁ -C ₆ alkoxy groups,
A C ₁ -C ₆ alkylamino group, a C ₁ -C ₆ alkylthio group,
Cyano group, phenyl group optionally substituted with Qa, Qa
A benzyl group optionally substituted with Qa, a styryl group optionally substituted with Qa, a cinnamyl group optionally substituted with Qa, a phenethyl group optionally substituted with Qa, And X represents a cyano group, a nitro group, a (C ₁ -C ₄ alkoxy) carbonyl group, or a (C ₁ -C ₄ alkyl) carbonyloxy group. Group,
(C ₁ -C ₄ alkoxy) carbonyloxy, methanesulfonyloxy, hydroxyl, ethynyl, amide, N
R ² R ³ , halogen atom, C ₁ -C ₄ alkyl group, C ₁ -C ₄
Represents a haloalkyl group or a phenyl group which may be substituted with Qa, Y is a hydrogen atom, C ₁ -C ₆ alkyl, C ₃ -C ₆ cycloalkyl groups, C ₁ -C ₆ haloalkyl groups, C ₁ -C ₆ alkoxycarbonyl group, dimethylaminocarbonyl group, 2-hydroxyethyl group, methoxymethyl group, acetyl group, methanesulfonyl group, dimethylaminosulfonyl group, Qa
Represents a phenyl group which may be substituted by Q or a benzyl group which may be substituted by Qa; Z represents an oxygen atom or a sulfur atom; L represents a single bond; and C ₁ -C which may be substituted by Qb.
₆ alkylene, C _2- which may be substituted by Qb
C ₆ alkenylene or optionally C ₂ -C ₄ alkynylene optionally substituted by Qb, where, R ¹ is C ₁ -C ₃
Alkyl, X represents a C ₁ -C ₃ alkyl group or a C ₁ -C ₃ haloalkyl group, Y represents a methyl group, and Z represents an oxygen atom, L is a single bond, substituted by Qb, C ₂ -C ₆ alkylene, C ₂ -C ₆ alkenylene optionally substituted by Qb or C ₂ -C ₄ alkynylene optionally substituted by Qb, Qb represents a methyl group, a methoxycarbonyl group, An ethoxycarbonyl group, a cyano group or a phenyl group; and n represents 0 or 1; A represents a single bond, CO, SO ₂ or an oxygen atom; B represents NR ² or NR ² NR ³ , A and L both represent a single bond, and when X represents a cyano group, B represents an oxygen atom or a sulfur atom, A represents a single bond, and L is Qb B represents oxygen when C ₁ -C ₆ alkylene optionally substituted by Qb, C ₂ -C ₆ alkenylene optionally substituted by Qb or C ₂ -C ₄ alkynylene optionally substituted by Qb, represents an atom or a sulfur atom, a represents NR ² is B when representing the CO, B when a represents SO ₂ represents NR ² or NR ² NR ^3, when a represents an oxygen atom B Represents NR ₂ , A and B may combine to form NR ² CONR ³ , and R ² and R ³ independently of one another are a hydrogen atom, a methyl group, a formyl group, (C ₁ -C ₄ alkoxy) carbonyl group, (C
It represents an ₁ -C ₄ alkyl) carbonyl group, C ₁ -C ₄ alkylsulfonyl group and a substituted group selected from phenylsulfonyl group. Or a salt thereof that is acceptable as a pesticide. 2. An agricultural chemical comprising the compound according to claim 1 as an active ingredient. 3. A herbicide comprising the compound according to claim 1 as an active ingredient. 4. The compound according to claim 1, wherein X represents a cyano group. 5. R-On-LAB represents a hydroxyl group, and R ¹ represents a C ₁ -C ₆ alkyl group, a C ₃ -C ₆ cycloalkyl group, a C ₁ -C ₆ haloalkyl group, Qa. Optionally substituted benzyl group, styryl group optionally substituted with Qa, cinnamyl group optionally substituted with Qa, phenethyl group optionally substituted with Qa or optionally substituted with Qa X represents a cyano group; Y represents a hydrogen atom, a C ₁ -C ₆ alkyl group, a C ₃ -C ₆ cycloalkyl group, a C ₁ -C ₆ haloalkyl group, a C ₁ -C 3 ₆ alkoxycarbonyl group, dimethylaminocarbonyl group, 2-hydroxyethyl group, methoxymethyl group, acetyl group, methanesulfonyl group, dimethylaminosulfonyl group, Qa
Represents a phenyl group optionally substituted with or a benzyl group optionally substituted with Qa, and Z represents an oxygen atom or a sulfur atom. The compound according to claim 1, which is represented by the formula: