JP2006232824A - Imidazole derivatives, methods for producing them, and herbicides containing them as active ingredients - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To obtain a herbicide having an exceedingly excellent control effect on harmful weeds in agricultural and horticultural cultivation situations and in a non-crop land. <P>SOLUTION: The herbicide comprises an imidazole derivative represented by general formula (1) as an active ingredient. The imidazole derivative exhibits excellent herbicidal activity with a small application amount without causing phytotoxicity. <P>COPYRIGHT: (C)2006,JPO&NCIPI

Description

  The present invention relates to imidazole derivatives, methods for producing them, and herbicides containing them as active ingredients.

Conventionally, many imidazole derivatives having physiological activities as agricultural chemicals such as herbicidal activity, insecticidal activity, and bactericidal activity are known, and have a substituted carbamoyl group at the 4-position of the imidazole ring represented by the following general formula (1) of the present invention There are no reports on 5- (fluoroalkyl) imidazole derivatives and no reports on their biological activity.
Moreover, 4-substituted carbamoyl-5-trifluoromethylimidazole derivatives having an oxytocin antagonistic action are known as approximate compounds of the present invention (see Patent Document 1), and these compounds have 4 atoms on the carbamoyl nitrogen atom. , 4-Difluoro-2,3,4,5-tetrahydro-1H-1-benzoazepine ring is completely different from the imidazole derivative (1) of the present invention.
International Publication No. 98/39325 Pamphlet

  An object of the present invention is to provide novel imidazole derivatives having excellent herbicidal activity and high selectivity, methods for producing them, and herbicides containing these derivatives as active ingredients.

  As a result of intensive studies to solve the above problems, the present inventor has demonstrated that the novel imidazole derivative represented by the following general formula (1) of the present invention exhibits excellent herbicidal activity without causing phytotoxicity at a low application rate. As a result, the present invention has been completed.

（式中、Ｒ^１は炭素数１〜６のフルオロアルキル基を表す。Ｒ^２は置換していてもよいカルバモイル基、カルボキシ基又はシアノ基を表す。Ｘは水素原子、ハロゲン原子、炭素数１〜６のアルキル基、炭素数１〜６のハロアルキル基、炭素数１〜６のアルコキシ基、炭素数１〜６のハロアルコキシ基、置換されていてもよいフェニルオキシ基、炭素数１〜６のアルキルチオ基、炭素数１〜６のハロアルキルチオ基、炭素数１〜６のアルキルスルフィニル基、炭素数１〜６のハロアルキルスルフィニル基、炭素数１〜６のアルキルスルホニル基、炭素数１〜６のハロアルキルスルホニル基、アミノ基、炭素数１〜６のアルキルアミノ基、ジ（炭素数１〜６のアルキル）アミノ基、炭素数１〜６のアシルアミノ基、炭素数１〜６のアルキルスルホニルアミノ基、水酸基、メルカプト基、カルボキシ基、シアノ基又はニトロ基を表し、ｎは０又は１〜５の整数を表す。ただし、ｎが２〜５の整数の場合Ｘは同一でも相異なってもよい。）で示されるイミダゾール誘導体に関するものである。 That is, the present invention relates to the general formula (1)

(In the formula, R ¹ represents a fluoroalkyl group having 1 to 6 carbon atoms. R ² represents an optionally substituted carbamoyl group, carboxy group, or cyano group. X represents a hydrogen atom, a halogen atom, or a carbon number of 1. -6 alkyl group, haloalkyl group having 1 to 6 carbon atoms, alkoxy group having 1 to 6 carbon atoms, haloalkoxy group having 1 to 6 carbon atoms, optionally substituted phenyloxy group, 1 to 6 carbon atoms Alkylthio group, haloalkylthio group having 1 to 6 carbon atoms, alkylsulfinyl group having 1 to 6 carbon atoms, haloalkylsulfinyl group having 1 to 6 carbon atoms, alkylsulfonyl group having 1 to 6 carbon atoms, haloalkyl having 1 to 6 carbon atoms Sulfonyl group, amino group, alkylamino group having 1 to 6 carbon atoms, di (alkyl having 1 to 6 carbon atoms) amino group, acylamino group having 1 to 6 carbon atoms, alkylsulfur group having 1 to 6 carbon atoms Nylamino group, hydroxyl group, mercapto group, carboxy group, cyano group or nitro group, n represents 0 or an integer of 1 to 5. However, when n is an integer of 2 to 5, X may be the same or different. It is related to an imidazole derivative represented by

More specifically, the present invention relates to the general formula (1), wherein R ² is a —CONR ³ R ⁴ group (R ³ and R ⁴ are each independently a hydrogen atom or an optionally substituted carbon atom having 1 to 12 carbon atoms). An alkyl group, an optionally substituted cycloalkyl group having 3 to 8 carbon atoms, an optionally substituted alkenyl group having 3 to 6 carbon atoms, an optionally substituted alkynyl group having 3 to 6 carbon atoms, and a substitution An optionally substituted aralkyl group having 7 to 11 carbon atoms, an optionally substituted phenyl group, an optionally substituted alkyloxy group having 1 to 12 carbon atoms, or an optionally substituted carbon group having 7 to 11 carbon atoms. Or an optionally substituted carbamoyl group represented by: R ³ and R ⁴ may form a heterocyclic ring which may be substituted together with the nitrogen atom to which they are bonded. Carboxy group or It relates imidazole derivatives which are anode group.

（式中、Ｒ^１、Ｘ及びｎは前記と同じ意味を表す。Ｒ^５は炭素数１〜６のアルキル基を表す。）で示されるイミダゾール誘導体のエステル部位を加水分解し、一般式(３)

（式中、Ｒ^１、Ｘ及びｎは前記と同じ意味を表す。）で示されるイミダゾール誘導体を製造し、次いでハロゲン化剤と反応させ、一般式(４)

（式中、Ｒ^１、Ｘ及びｎは前記と同じ意味を表す。Ｙはハロゲン原子を表す。）で示されるイミダゾール誘導体を得、次いで一般式(５)

（式中、Ｒ^３及びＲ^４は前記と同じ意味を表す。）で示されるアミン類を場合によっては塩基の存在下に反応させ、一般式(６)

（式中、Ｒ^１、Ｒ^３、Ｒ^４、Ｘ及びｎは前記と同じ意味を表す。）で示されるイミダゾール誘導体の製造方法に関する。 The present invention also provides a general formula (2)

(Wherein R ¹ , X and n represent the same meaning as described above. R ⁵ represents an alkyl group having 1 to 6 carbon atoms.) The ester moiety of the imidazole derivative represented by the general formula (3 )

(Wherein R ¹ , X and n represent the same meaning as described above) are produced, and then reacted with a halogenating agent to produce a compound represented by the general formula (4)

(Wherein R ¹ , X and n represent the same meaning as described above, Y represents a halogen atom), and then the general formula (5)

(Wherein R ³ and R ⁴ represent the same meaning as described above), the amines represented by the general formula (6)

(Wherein R ¹ , R ³ , R ⁴ , X and n represent the same meaning as described above).

（式中、Ｒ^１、Ｒ^５、Ｘ及びｎは前記と同じ意味を表す。）で示されるイミダゾール誘導体と、一般式(７)

（式中、Ｒ^３ａは水素原子、置換されていてもよい炭素数１〜１２のアルキル基、置換されていてもよい炭素数３〜８のシクロアルキル基、置換されていてもよい炭素数３〜６のアルケニル基、置換されていてもよい炭素数３〜６のアルキニル基、置換されていてもよい炭素数７〜１１のアラルキル基、置換されていてもよいフェニル基、置換されていてもよい炭素数１〜１２のアルコキシ基又は置換されていてもよい炭素数７〜１１のアラルキルオキシ基を表す。）で示されるアミン類を場合によっては塩基の存在下に反応させ、一般式(６ａ)

（式中、Ｒ^１、Ｒ^３ａ、Ｘ及びｎは前記と同じ意味を表す。）で示されるイミダゾール誘導体の製造方法に関する。 Furthermore, the present invention provides a general formula (2)

(Wherein R ¹ , R ⁵ , X and n represent the same meaning as described above) and the general formula (7)

Wherein R ^3a is a hydrogen atom, an optionally substituted alkyl group having 1 to 12 carbon atoms, an optionally substituted cycloalkyl group having 3 to 8 carbon atoms, or an optionally substituted carbon number 3 -6 alkenyl group, optionally substituted alkynyl group having 3 to 6 carbon atoms, optionally substituted aralkyl group having 7 to 11 carbon atoms, optionally substituted phenyl group, optionally substituted A suitable alkoxy group having 1 to 12 carbon atoms or an optionally substituted aralkyloxy group having 7 to 11 carbon atoms) is optionally reacted in the presence of a base to give a general formula (6a )

(Wherein R ¹ , R ^3a , X and n represent the same meaning as described above).

（式中、Ｒ^１、Ｘ及びｎは前記と同じ意味を表す。）で示されるイミダゾール誘導体を脱水剤の存在下に反応させ、一般式(８)

（式中、Ｒ^１、Ｘ及びｎは前記と同じ意味を表す。）で示されるイミダゾール誘導体の製造方法に関する。 Furthermore, the present invention relates to the general formula (6b)

(Wherein R ¹ , X and n represent the same meaning as described above) are reacted in the presence of a dehydrating agent to give a general formula (8)

(Wherein R ¹ , X and n represent the same meaning as described above).

（式中、Ｒ^１、Ｘ及びｎは前記と同じ意味を表す。Ｒ^２ａは-ＣＯＮＲ^３Ｒ^４基（Ｒ^３及びＲ^４は前記と同じ意味を表す。）で示される置換していてもよいカルバモイル基、又はシアノ基を表す。）で示されるイミダゾール誘導体を有効成分とする除草剤に関するものである。以下、本発明をさらに詳細に説明する。 The present invention also provides a compound of the general formula (1a)

(Wherein R ¹ , X and n represent the same meaning as described above. R ^2a represents a —CONR ³ R ⁴ group (R ³ and R ⁴ represent the same meaning as described above)) It represents a carbamoyl group or a cyano group). Hereinafter, the present invention will be described in more detail.

  The herbicide containing the imidazole derivative of the present invention as an active ingredient has an extremely excellent control effect against harmful weeds in agricultural or horticultural situations or non-agricultural land, and is effective as a herbicide for agricultural or horticultural or non-agricultural land. is there. Since the compound of the present invention exhibits selective herbicidal activity between the following weeds and crops, it can be used as a selective herbicide.

The grasses weeds, Alopecurus (Alopecurus), oats (Avena), Bromus Catharticus (Bromus), sedge (Cyperus), crabgrass (Digitaria), barnyard grass (Echinochloa), water chestnut (Eleocharis), goosegrass (Eleusine), Monochoria (Monochoria) , fall panicum (Panicum), timothy grass (Phleum), bluegrass (Poa), Alismataceae (Sagittaria), bulrush (Scirpus), green foxtail (Setaria), there is such as Johnson grass (Sorghum).

The broad-leaved weeds, velvetleaf (Abutilon), Amaranthus lividus (Amaranthus), ragweed (Ambrosia), Bidens pilosa (Bidens), goosefoot (Chenopodium), cleavers (Galium), convolvulus (Ipomoea), false pimpernel (Lindernia), knotweed (persicaria), purslane (Portulaca), toothcup (Rotala), common chickweed (Stellaria), violet (Viola), and the like cocklebur (Xanthium).

Examples of useful cultivated plants or crops in the field where the compound of the present invention can be applied include barley ( Hordeum ), rice ( Oryza ), sugar cane ( Saccharum ), wheat ( Triticum ), and corn ( Zea ).

Broad-leaved crops include peanut ( Arachis ), sugar beet ( Beta ), rape ( Brassica ), soybean ( Glycine ), cotton ( Gossypium ), and tomato ( Lycopersicon ).

  Needless to say, the use of the compound of the general formula (1) according to the present invention as a herbicide is not limited to the weeds and crops exemplified above.

In the present invention, definitions of substituents represented by R ¹ , R ³ , R ^3a , R ⁴ , R ⁵ and X are shown below.

Examples of the fluoroalkyl group having 1 to 6 carbon atoms represented by R ¹ include a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, a 2,2,2-trifluoromethyl group, and a pentafluoroethyl group. Can do.

The ^optionally substituted alkyl group represented by R ³ , R ^3a and R ⁴ may be linear or branched, and may be a methyl group, an ethyl group, Propyl group, isopropyl group, butyl group, isobutyl group, s-butyl group, tert-butyl group, pentyl group, isoamyl group, neopentyl group, 2-pentyl group, 3-pentyl group, 2-methylbutyl group, t-pentyl group Hexyl group, isohexyl group, 2-ethylbutyl group, 4-methylpentyl group, heptyl group, 2-heptyl group, octyl group, decyl group, undecyl group, dodecyl group and the like. These alkyl groups include a halogen atom, a cycloalkyl group having 3 to 8 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, an alkylthio group having 1 to 6 carbon atoms, an optionally substituted phenyloxy group, and 1 to 1 carbon atom. 1 or more may be substituted with 6 alkoxycarbonyl groups, carboxy groups, acyl groups, cyano groups, etc. More specifically, 2-chloroethyl group, 3-chloropropyl group, difluoromethyl group, 2,2- A difluoroethyl group, a 2,2,2-trifluoroethyl group, a 2,2,2-trifluoro-1-methylethyl group, a 3-fluoropropyl group, a cyclopropylmethyl group, a cyclopentylmethyl group, a cyclohexylmethyl group, 2-methylthioethyl group, 2-methylsulfinylethyl group, 2-methylsulfonylethyl group, methoxymethyl group, ethoxymethyl group, 2-methoxy Tyl group, 2-chloroethoxymethyl group, 1,1-dimethyl-2-methylthioethyl group, methoxycarbonylmethyl group, ethoxycarbonylmethyl group, 1-methoxycarbonylethyl group, 1-ethoxycarbonylethyl group, 2-ethoxycarbonyl Ethyl group, carboxymethyl group, acetonyl group, 1-acetylethyl group, 3-acetylpropyl group, phenacyl group, 4-chlorophenacyl group, 2,4-difluorophenacyl group, 4-methylphenacyl group, 4- Isopropylphenacyl group, 4-isobutylphenacyl group, 4-cyclohexylphenacyl group, 4-cyanophenacyl group, 4-nitrophenacyl group, 2-cyano-2-propyl group, 2-cyano-2-butyl group, 3 -Cyano-3-pentyl group, 2-cyano-4-methyl-2-pentyl group, 1-cyano-1-phenyloxyethyl group, 1-sia -1- (4-chlorophenyl) ethyl group, 1-cyano-1-methyl-2- (4-fluorophenyl oxy) can be exemplified an ethyl group or the like.

Examples of the optionally substituted cycloalkyl group represented by R ³ , R ^3a and R ⁴ having 3 to 8 carbon atoms include cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group and cyclooctyl group. Eight cycloalkyl groups can be exemplified. In addition, these cycloalkyl groups may be substituted with a halogen atom, an alkyl group having 1 to 6 carbon atoms, an alkoxycarbonyl group having 1 to 6 carbon atoms, and more specifically, a 1-methylcyclopropyl group. Examples include 2,2-dimethylcyclopropyl group, 2-fluorocyclopropyl group, 2-methoxycarbonylcyclopropyl group, 2-methylcyclopentyl group, 3-methylcyclopentyl group, and the like.

The ^optionally substituted alkenyl group having 3 to 6 carbon atoms represented by R ³ , R ^3a and R ⁴ may be linear, branched or cyclic, 1-propenyl group, Allyl group, 2-methyl-2-propenyl group, 2-butenyl group, 3-butenyl group, 2-pentenyl group, 3-pentenyl group, 1-cyclopentenyl group, 2-hexenyl group, 3-hexenyl group, 1- Examples thereof include a cyclohexenyl group, a 2-heptenyl group, and a 1-cyclooctenyl group. These alkenyl groups may be substituted with a halogen atom, and examples thereof include a 2-chloro-2-propenyl group, a 3-chloropropenyl group, and a 4-chloro-2-butenyl group.

The ^optionally substituted alkynyl group having 3 to 6 carbon atoms represented by R ³ , R ^3a and R ⁴ may be either linear or branched, propargyl group, 1-butyne Examples include a -3-yl group, a 3-methyl-1-butyn-3-yl group, a 2-butynyl group, a 2-pentynyl group, and a 3-pentynyl group. In addition, these alkynyl groups may be substituted with a halogen atom or the like, for example, 3-fluoro-2-propynyl group, 3-chloro-2-propynyl group, 3-bromo-2-propynyl group, 4-bromo Examples include a -2-butynyl group, a 4-bromo-3-butynyl group, and the like.

Examples of the optionally substituted aralkyl group having 7 to 11 carbon atoms represented by R ³ , R ^3a and R ⁴ include a benzyl group, a 1-phenylethyl group, a 2-phenylethyl group, a 1-phenylpropyl group, Examples thereof include 1-naphthylmethyl group, 2-naphthylmethyl group and the like. These aralkyl groups are halogen atoms, alkyl groups having 1 to 12 carbon atoms, haloalkyl groups having 1 to 6 carbon atoms, alkyloxy groups having 1 to 6 carbon atoms, haloalkyloxy groups having 1 to 6 carbon atoms, and 1 to 1 carbon atoms. 6 or more alkylthio groups, 1 to 6 alkylsulfonyl groups, 1 to 6 alkyloxycarbonyl groups, carboxy groups, optionally substituted carbamoyl groups, cyano groups, nitro groups, etc. May be. More specifically, 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, 3,5-difluorobenzyl group, 3,5-dichlorobenzyl group, 3,5-dibromobenzyl group, 2-methylbenzyl group, 3-methylbenzyl group, 4 -Methylbenzyl group, 2,4-dimethylbenzyl group, 3,5-dimethylbenzyl group, 2-trifluoromethylbenzyl group, 3-trifluoromethylbenzyl group, 4-trifluoromethylbenzyl group, 3,5-bis (Trifluoromethyl) benzyl group, 2,4-bis (trifluoromethyl) benzyl group, 2-methoxycarbonylbenzyl group, 3-methoxycarbonylbenzyl group, 4-methoxy Carbonylbenzyl group, 3-carboxybenzyl group, 4-carboxybenzyl group, 3- (N, N-dimethylcarbamoyl) benzyl group, 4- (N, N-dimethylcarbamoyl) benzyl group, 3- (N, N-diethyl) Carbamoyl) benzyl group, 3- (N-ethyl-N-propylcarbamoyl) benzyl group, 3-cyanobenzyl group, 4-cyanobenzyl group, 2-methoxybenzyl group, 3-methoxybenzyl group, 4-methoxybenzyl group, 3,4-dimethoxybenzyl group, 4-trifluoromethoxybenzyl group, 4-phenoxybenzyl group, 4-methylthiobenzyl group, 4-methylsulfonylbenzyl group, 2-nitrobenzyl group, 3-nitrobenzyl group, 4-nitro Benzyl group, 1- (2-fluorophenyl) ethyl group, 1- (2-chlorophenyl) ethyl group, 1- (2-bromophenyl) ethyl group, 1- (3-fluoro Enyl) ethyl, 1- (3-chlorophenyl) ethyl, 1- (3-bromophenyl) ethyl, 1- (4-fluorophenyl) ethyl, 1- (4-chlorophenyl) ethyl, 1- ( 4-bromophenyl) ethyl group, 1- (2-trifluoromethylphenyl) ethyl group, 1- (3-trifluoromethylphenyl) ethyl group, 1- (4-trifluoromethylphenyl) ethyl group, 2- ( Examples thereof include 3-bromophenyl) ethyl group, 2- (3-trifluoromethylphenyl) ethyl group, 3-phenylpropyl group, 4-phenylbutyl group and the like.

As the ^optionally substituted aromatic group represented by R ³ , R ^3a and R ⁴ , as a substituent on the aromatic ring, a halogen atom, an alkyl group having 1 to 12 carbon atoms, or an alkyl group having 1 to 6 carbon atoms A haloalkyl group, an acyl group having 1 to 6 carbon atoms, an alkyl group having 1 to 12 carbon atoms substituted with an alkoxyimino group having 1 to 6 carbon atoms, an alkyloxycarbonyl group having 1 to 6 carbon atoms, a carboxy group, and a cyano group , An alkyloxy group having 1 to 6 carbon atoms, an aryloxy group, a haloalkyloxy group having 1 to 6 carbon atoms, an alkylthio group having 1 to 6 carbon atoms, an alkylsulfinyl group having 1 to 6 carbon atoms, and an alkyl group having 1 to 6 carbon atoms Even if it has one or more alkylsulfonyl groups, haloalkylthio groups having 1 to 6 carbon atoms, haloalkylsulfinyl groups having 1 to 6 carbon atoms, haloalkylsulfonyl groups having 1 to 6 carbon atoms, nitro groups, etc. Good aromatic groups can be exemplified. Examples of the aromatic group include phenyl group, naphthyl group, furyl group, thienyl group, pyrrolyl group, imidazolyl group, pyrazolyl group, isothiazolyl group, isoxazolyl group, pyridyl group, pyrazinyl group, pyrimidinyl group and the like.

  More specifically, a phenyl group, 2-fluorophenyl group, 2-chlorophenyl group, 2-bromophenyl group, 2-iodophenyl group, 3-fluorophenyl group, 3-chlorophenyl group, 4-fluorophenyl group, 4 -Chlorophenyl group, 4-bromophenyl group, 2,4-difluorophenyl group, 2,4-dichlorophenyl group, 3,5-difluorophenyl group, 3,5-dichlorophenyl group, 3-chloro-2,4-difluorophenyl Group, 2,4,5-trichlorophenyl group, 2,4-dichloro-3-methylphenyl group, 2,4-dichloro-5-methoxyphenyl group, 2,4-dichloro-5-isopropyloxyphenyl group, 4 -Chloro-2-fluoro-5-methoxyphenyl group, 4-chloro-2-fluoro-5-isopropyloxyphenyl group, 4-chloro-2-fluoro-5-cyclopentyloxyphenyl group, 4- Chloro-2-fluoro-5-propargyloxyphenyl group, 4-chloro-2-fluoro-5- (1-butyn-3-yloxy) phenyl group, 2-fluoro-4-trifluoromethylphenyl group, 2-chloro -4-trifluoromethylphenyl group, 2-chloro-5-trifluoromethylphenyl group, 4-fluoro-3-phenoxyphenyl group, 2-fluoro-5-nitrophenyl group, 2,4-difluoro-5-nitro Phenyl group, 2-methylphenyl group, 3-methylphenyl group, 4-methylphenyl group, 2,4-dimethylphenyl group, 4-ethylphenyl group, 4-isopropylphenyl group, 2-s-butylphenyl group, 2 -t-butylphenyl group, 4-t-butylphenyl group, 2-trifluoromethylphenyl group, 3-trifluoromethylphenyl group, 4-trifluoromethylphenyl group, 2,4-bis (trifluoro Methyl) phenyl group, 3,5-bis (trifluoromethyl) phenyl group, 2-acetylphenyl group, 4-acetylphenyl group, 4-isovalerylphenyl group, 2-methoxycarbonylphenyl group, 2-ethoxycarbonylphenyl Group, 3-methoxycarbonylphenyl group, 4-methoxycarbonylphenyl group, 2-carboxyphenyl group, 4-carboxyphenyl group, 2-cyanophenyl group, 4-cyanophenyl group, 2-methoxyphenyl group, 3-methoxyphenyl Group, 4-methoxyphenyl group, 3,4-dimethoxyphenyl group, 4-isopropyloxyphenyl group, 4-t-butyloxyphenyl group, 3-trifluoromethyloxyphenyl group, 4-trifluoromethyloxyphenyl group, 2-phenoxyphenyl group, 3-phenoxyphenyl group, 4-phenoxyphenyl group, 2-methyl Ruthiophenyl group, 4-methylthiophenyl group, 2-methylsulfinylphenyl group, 4-methylsulfinylphenyl group, 2-methylsulfonylphenyl group, 4-methylsulfonylphenyl group, 4-trifluoromethylthiophenyl group, 4-trifluoro Methylsulfinylphenyl group, 4-trifluoromethylsulfonylphenyl group, 2-nitrophenyl group, 4-nitrophenyl group, 1-methyl-2-pyrazolyl group, 1-ethyl-2-pyrazolyl group, 1,3-dimethyl- 5-pyrazolyl group, 1-methyl-2-imidazolyl group, 3-thienyl group, 2-isopropyl-3-thienyl group, 2- (1,3-dimethylbutyl) -3-thienyl group, 2-methoxycarbonyl-3 -Thienyl group, 3-isoxazolyl group, 5-methyl-3-isoxazolyl group, 3-methyl-5-isothiazolyl group, 2-thiazolyl group 5-bromo-2-thiazolyl group, 4-methyl-2-thiazolyl group, 4,5-dimethyl-2-thiazolyl group, 4- (4-bromophenyl) -2-thiazolyl group, 1,3,4- Thiadiazol-2-yl group, 5-ethyl-1,3,4-thiadiazol-2-yl group, 5-t-butyl-1,3,4-thiadiazol-2-yl group, 5-methylthio-1,3 , 4-thiadiazol-2-yl group, 5-ethylthio-1,3,4-thiadiazol-2-yl group, 5-trifluoromethyl-1,3,4-thiadiazol-2-yl group, 2-pyridyl group 5-fluoro-2-pyridyl group, 5-chloro-2-pyridyl group, 5-bromo-2-pyridyl group, 5-trifluoromethyl-3-chloro-2-pyridyl group, 5-bromo-3-methyl -2-pyridyl group, 3-bromo-5-methyl-2-pyridyl group, 3,5-dichloro-2-pyridyl group, 3-methyl-2-pyridyl group, 3,5-dimethyl-2-pyridyl group Group, 2-methoxy-5-pyridyl group, 2-pyrimidinyl group, 5-bromo-2-pyrimidinyl group, 4-chloro-6-methyl-2-pyrimidinyl group, 4-chloro-6-methoxy-2-pyrimidinyl group Examples include 4-methyl-6-methoxy-2-pyrimidinyl group, 4,6-dichloro-2-pyrimidinyl group, 4,6-dimethyl-2-pyrimidinyl group, 4,6-dimethoxy-2-pyrimidinyl group, etc. be able to.

Examples of the optionally substituted alkoxy group represented by R ³ , R ^3a and R ⁴ include a methoxy group, an ethoxy group, a propyloxy group, an isopropyloxy group, a butyloxy group, an isobutyloxy group, s-Butyloxy, pentyloxy, isoamyloxy, neopentyloxy, 2-pentyloxy, 3-pentyloxy, 2-methylbutyloxy, hexyloxy, isohexyloxy, 3-methylpentyl Examples thereof include an oxy group, 4-methylpentyloxy group, heptyloxy group, 2-heptyloxy group, octyloxy group, decyloxy group, undecyloxy group, dodecyloxy group and the like. These alkyl groups are halogen atoms, cycloalkyl groups having 3 to 8 carbon atoms, alkylthio groups having 1 to 6 carbon atoms, alkylsulfinyl groups having 1 to 6 carbon atoms, alkylsulfonyl groups having 1 to 6 carbon atoms, and 1 carbon atom. 1 to 6 alkoxy groups, 1 to 6 alkoxycarbonyl groups, acyl groups and the like may be substituted, and more specifically, 2-chloroethyloxy group, 3-chloropropyloxy group, difluoromethoxy Group, 3-fluoropropyloxy group, cyclopropylmethoxy group, cyclopentylmethoxy group, cyclohexylmethoxy group, 2-methylthioethoxy group, methoxymethoxy group, ethoxymethoxy group, 2-methoxyethoxy group, 2-chloroethoxymethoxy group, methoxy Carbonylmethoxy group, ethoxycarbonylmethoxy group, 1-methoxycarbo Nylethoxy group, 1-ethoxycarbonylethoxy group, 2-ethoxycarbonylethoxy group, 1-acetylethoxy group, benzoylmethoxy group, 4-chlorobenzoylmethoxy group, 2,4-difluorobenzoylmethoxy group, 4-methylbenzoylmethoxy group, Examples include 4-isopropylbenzoylmethoxy group, 4-isobutylbenzoylmethoxy group, 4-cyclohexylbenzoylmethoxy group, 4-cyanobenzoylmethoxy group, 4-nitrobenzoylmethoxy group, and the like.

The optionally substituted aralkyloxy group having 7 to 11 carbon atoms represented by R ³ , R ^3a and R ⁴ includes a benzyloxy group, 4-fluorobenzyloxy group, 3-fluorobenzyloxy group, 2- Fluorobenzyloxy group, 4-chlorobenzyloxy group, 3-chlorobenzyloxy group, 2-chlorobenzyloxy group, 4-bromobenzyloxy group, 3-bromobenzyloxy group, 2-bromobenzyloxy group, 4-tri Fluoromethylbenzyloxy group, 3-trifluoromethylbenzyloxy group, 4-methoxybenzyloxy group, 3-methoxybenzyloxy group, 4-trifluoromethoxybenzyloxy group, 4-methylbenzyloxy group, 3-methylbenzyloxy Group, 2-methylbenzyloxy group, 4-t-butylbenzyloxy group, 2,3-dichlorobenzyl Oxy group, 2,4-dichlorobenzyloxy group, 2,6-dichlorobenzyloxy group, 3,4-dichlorobenzyloxy group, 2,4-difluorobenzyloxy group, 3,4-difluorobenzyloxy group, 3, Examples include 5-difluorobenzyloxy group, α-phenethyloxy group, β-phenethyloxy group and the like.

Examples of the optionally substituted heterocyclic ring formed integrally with the nitrogen atom to which R ³ and R ⁴ are bonded include pyrrole, pyrroline, pyrrolidine, imidazole, imidazoline, imidazolidine, pyrazole, pyrazoline, pyrazolidine, piperidine, piperazine , Indole, indoline, isoindole, 1H-indazole, purine, oxazoline, oxazolidine, isoxazoline, isoxazolidine, thiazoline, thiazolidine, morpholine, thiomorpholine, aziridine, azocane, tetrahydrooxazine, and the like. One or more atoms may be substituted with an atom or an alkyl group having 1 to 6 carbon atoms.

The alkyl group having 1 to 6 carbon atoms represented by R ⁵ may be linear or branched, and may be a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, s -Butyl group, t-butyl group, pentyl group, hexyl group and the like can be exemplified.

X represents hydrogen atom; halogen atom such as fluorine atom, chlorine atom, bromine atom; carbon such as methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, s-butyl group, t-butyl group 1-6 alkyl groups; fluoromethyl group, chloromethyl group, bromomethyl group, difluoromethyl group, trichloromethyl group, trifluoromethyl group, 1-chloroethyl group, 2-chloroethyl group, pentafluoroethyl group, 3-chloro C1-C6 haloalkyl groups such as propyl group; C1-C6 such as methoxy group, ethoxy group, propyloxy group, isopropyloxy group, butyloxy group, isobutyloxy group, s-butyloxy group, t-butyloxy group Alkoxy groups of: trifluoromethoxy group, difluoromethoxy group, 2-chloroethoxy group, 3-chloropropyl 1 to 6 carbon haloalkoxy groups such as a pyroxy group, 2-chloro-1-methylethoxy group, 2,2,2-trifluoroethoxy group; phenyloxy group, 4-methylphenyloxy group, 3-chlorophenyloxy Phenyloxy group which may be substituted such as 2-fluorophenyloxy group, 4-fluorophenyloxy group; methylthio group, ethylthio group, propylthio group, isopropylthio group, butylthio group, isobutylthio group, s-butylthio group Group, C1-C6 alkylthio group such as t-butylthio group; C1 such as chloromethylthio group, difluoromethylthio group, trifluoromethylthio group, trichloromethylthio group, 2,2,2-trifluoroethylthio group, etc. ~ 6 haloalkylthio groups; methylsulfinyl group, ethylsulfinyl group, propylsulfi group Alkyl group, isopropylsulfinyl group, butylsulfinyl group, isobutylsulfinyl group, s-butylsulfinyl group, t-butylsulfinyl group, etc., alkylsulfinyl group having 1 to 6 carbon atoms; chloromethylsulfinyl group, difluoromethylsulfinyl group, trifluoro C1-C6 haloalkylsulfinyl groups such as methylsulfinyl group, trichloromethylsulfinyl group, 2,2,2-trifluoroethylsulfinyl group; methylsulfonyl group, ethylsulfonyl group, propylsulfonyl group, isopropylsulfonyl group, butylsulfonyl Group, an isobutylsulfonyl group, a s-butylsulfonyl group, a t-butylsulfonyl group, etc., an alkylsulfonyl group having 1 to 6 carbon atoms; a chloromethylsulfonyl group, a difluoromethylsulfonyl group, a trifluoro group C1-C6 haloalkylsulfonyl group such as methylsulfonyl group, trichloromethylsulfonyl group, 2,2,2-trifluoroethylsulfonyl group; amino group; methylamino group, ethylamino group, propylamino group, isopropylamino group An alkylamino group having 1 to 6 carbon atoms such as a butylamino group; a di (C1-6 alkyl) amino group such as a dimethylamino group, a diethylamino group, or a methylpropylamino group; a formylamino group, an acetylamino group, C1-C6 acylamino group such as propionylamino group; C1-C6 alkylsulfonylamino group such as methylsulfonylamino group and ethylsulfonylamino group, hydroxyl group, mercapto group, carboxy group, cyano group or nitro group Can be illustrated.

Next, the manufacturing method of the imidazole derivative of this invention is demonstrated in detail. The starting material imidoyl halides are known methods (Journal of Organic Chemistry, 58,
32-35 (1993)). In addition, some of the imidazole derivatives represented by the general formula (2) are known compounds, and can be easily synthesized according to a known method (Journal of Fluorine Chemistry, 74, 279-282 (1995)).

（式中、Ｒ^１、Ｒ^３、Ｘ及びｎは前記と同じ意味を表す。）
本反応では、塩基を用いる通常のエステル加水分解反応に利用される方法を用いることにより容易に目的物を得ることができ、塩基としては、水酸化リチウム、水酸化ナトリウム、水酸化カリウム、水酸化カルシウム等のアルカリ金属水酸化物やアルカリ土類金属水酸化物を用い、水、あるいはアセトニトリル、テトラヒドロフラン（ＴＨＦ）、１,４-ジオキサン、メタノール、エタノール等の水と均一に混合する有機溶媒と水との混合溶媒中で行うことができる。塩基は基質に対して１当量〜大過剰量用いて反応させることにより、収率よく目的物を得ることができる。
反応は０℃から１５０℃の範囲から適宜選ばれた温度で実施することができる。反応終了後は、通常の後処理操作により目的物を得ることができるが、必要であれば再結晶等により精製することもできる。 Production method-1 is a method for producing imidazole-4-carboxylic acid derivative (3) by hydrolyzing imidazole-4-carboxylic acid ester derivative (2).
[Production Method-1]

(In the formula, R ¹ , R ³ , X and n represent the same meaning as described above.)
In this reaction, the target product can be easily obtained by using a method utilized for a normal ester hydrolysis reaction using a base. As the base, lithium hydroxide, sodium hydroxide, potassium hydroxide, hydroxide Organic solvent and water that is mixed uniformly with water or water such as acetonitrile, tetrahydrofuran (THF), 1,4-dioxane, methanol, ethanol, etc. using alkali metal hydroxide or alkaline earth metal hydroxide such as calcium In a mixed solvent. The target can be obtained in high yield by reacting the base with 1 equivalent to a large excess of the substrate.
The reaction can be carried out at a temperature appropriately selected from the range of 0 ° C to 150 ° C. After completion of the reaction, the desired product can be obtained by ordinary post-treatment operations, but can be purified by recrystallization or the like if necessary.

（式中、Ｒ^１、Ｘ、ｎ及びＹは前記と同じ意味を表す。）
ハロゲン化剤としては、チオニルクロリド、三塩化リン、五塩化リン、オキシ塩化リン、三臭化リン、フルオロ硫酸等を例示することができ、これらのハロゲン化剤は基質に対して等量以上用いることにより収率よく目的物を得ることができる。反応は無溶媒中あるいはベンゼン、トルエン、キシレン、クロロベンゼン、クロロホルム、ジクロロメタン等の反応に害を与えない溶媒中で実施することができる。反応は０℃から１８０℃の範囲から適宜選ばれた温度で実施することができる。
また、酸クロリド誘導体を製造した後、フッ化カリウム、フッ化セシウム、フッ化アンモニウム、トリフェニルメチルホスホニウムフルオリド等の金属フッ化物、フッ化アンモニウム、フッ化ホスホニウム等のフッ化物を用いて酸フルオリド誘導体へと変換することもできる（特開平９-１７６１２６号公報）。
反応終了後は、溶媒や過剰のハロゲン化試剤を、例えば加熱減圧下に除去することにより、容易に目的とするイミダゾール-４-カルボン酸ハライド誘導体(４)を得ることができ、また、このものは単離することなく次の反応に使用することもできる。 Production method-2 is a method for producing an acid halide derivative (4) from an imidazole-4-carboxylic acid derivative (3) using a halogenating agent.
[Production method-2]

(In the formula, R ¹ , X, n and Y have the same meaning as described above.)
Examples of the halogenating agent include thionyl chloride, phosphorus trichloride, phosphorus pentachloride, phosphorus oxychloride, phosphorus tribromide, fluorosulfuric acid, etc., and these halogenating agents are used in an equivalent amount or more with respect to the substrate. As a result, the target product can be obtained with good yield. The reaction can be carried out in the absence of a solvent or in a solvent that does not harm the reaction, such as benzene, toluene, xylene, chlorobenzene, chloroform, dichloromethane. The reaction can be carried out at a temperature appropriately selected from the range of 0 ° C to 180 ° C.
In addition, after producing an acid chloride derivative, acid fluoride using a metal fluoride such as potassium fluoride, cesium fluoride, ammonium fluoride, triphenylmethylphosphonium fluoride, fluoride such as ammonium fluoride, phosphonium fluoride, etc. It can also be converted into a derivative (Japanese Patent Laid-Open No. 9-176126).
After completion of the reaction, the target imidazole-4-carboxylic acid halide derivative (4) can be easily obtained by removing the solvent and the excess halogenated reagent under, for example, heating under reduced pressure. Can also be used in the next reaction without isolation.

（式中、Ｒ^１、Ｒ^３、Ｒ^４、Ｘ、ｎ及びＹは前記と同じ意味を表す。）
本製造方法において用いることができる塩基としては、水素化ナトリウム、ナトリウムアミド、炭酸ナトリウム、炭酸カリウム、ナトリウムメトキシド、ナトリウムエトキシド、カリウム-ｔ-ブトキシド、水酸化ナトリウム、水酸化カリウム等のアルカリ金属塩基、トリエチルアミン、トリブチルアミン、Ｎ-メチルモルホリン、ピリジン、ジメチルアニリン等を例示することができる。塩基の使用量は反応基質に対して等量以上用いて反応を実施することにより、収率良く目的物を得ることができる。
反応は有機溶媒中で行うことが好ましく、ベンゼン、トルエン、キシレン、ＴＨＦ、ジエチルエーテル、クロロホルム、ジクロロメタン、アセトン、エチルメチルケトン、酢酸エチル、酢酸ブチル、Ｎ,Ｎ-ジメチルホルムアミド（ＤＭＦ）等を用いることができる。反応は−３０℃から６０℃の範囲から適宜選ばれた温度で実施することができる。
反応終了後は、通常の後処理操作により目的物を得ることができるが、必要であればカラムクロマトグラフィーあるいは再結晶等により精製することもできる。 Production method-3 is a method for producing the imidazole-4-carboxamide derivative (6) of the present invention by reacting the imidazole-4-carboxylic acid halide derivative (4) with amines (5) in the presence of a base. It is.
[Production Method-3]

(Wherein R ¹ , R ³ , R ⁴ , X, n and Y have the same meaning as described above).
Examples of the base that can be used in this production method include alkali metals such as sodium hydride, sodium amide, sodium carbonate, potassium carbonate, sodium methoxide, sodium ethoxide, potassium t-butoxide, sodium hydroxide, potassium hydroxide and the like. Examples include base, triethylamine, tributylamine, N-methylmorpholine, pyridine, dimethylaniline and the like. The target product can be obtained in good yield by carrying out the reaction with the use amount of the base equal to or more than the reaction substrate.
The reaction is preferably carried out in an organic solvent, and benzene, toluene, xylene, THF, diethyl ether, chloroform, dichloromethane, acetone, ethyl methyl ketone, ethyl acetate, butyl acetate, N, N-dimethylformamide (DMF), etc. are used. be able to. The reaction can be carried out at a temperature appropriately selected from the range of -30 ° C to 60 ° C.
After completion of the reaction, the desired product can be obtained by ordinary post-treatment operations, but can be purified by column chromatography or recrystallization if necessary.

（式中、Ｒ^１、Ｒ^３ａ、Ｒ^５、Ｘ及びｎは前記と同じ意味を表す。）
本反応は、トリエチルアミン、トリブチルアミン、ジメチルアニリン、Ｎ-メチルモルホリン、ピリジン等の有機アミン塩基の存在下に実施することが収率の良い点で好ましい。塩基の使用量は特に限定されるものではなく、１〜５等量程度使用することにより収率よく目的物を得られる点で好ましい。
反応は有機溶媒中で行うことが好ましく、ベンゼン、トルエン、キシレン、ＴＨＦ、ジエチルエーテル、クロロホルム、ジクロロメタン、アセトン、エチルメチルケトン、メタノール、エタノール、プロピルアルコール、イソプロピルアルコール、ｔ-ブチルアルコール、酢酸エチル、酢酸ブチル、ＤＭＦ、ジメチルスルホキシド（ＤＭＳＯ）等を用いることができる。反応は室温から溶媒還流温度から選ばれた温度で実施することができる。 Production method-4 is a method for producing the imidazole-4-carboxamide derivative (6a) of the present invention by reacting the imidazole derivative (2) with the primary amines (7) in the presence of a base.
[Production Method-4]

(Wherein R ¹ , R ^3a , R ⁵ , X and n represent the same meaning as described above.)
This reaction is preferably carried out in the presence of an organic amine base such as triethylamine, tributylamine, dimethylaniline, N-methylmorpholine, pyridine or the like in terms of a good yield. The amount of the base used is not particularly limited, and it is preferable in that the target product can be obtained with good yield by using about 1 to 5 equivalents.
The reaction is preferably carried out in an organic solvent, such as benzene, toluene, xylene, THF, diethyl ether, chloroform, dichloromethane, acetone, ethyl methyl ketone, methanol, ethanol, propyl alcohol, isopropyl alcohol, t-butyl alcohol, ethyl acetate, Butyl acetate, DMF, dimethyl sulfoxide (DMSO) and the like can be used. The reaction can be carried out at a temperature selected from room temperature to the solvent reflux temperature.

（式中、Ｒ^１、Ｘ及びｎは前記と同じ意味を表す。）
本製造方法において用いることができる脱水剤としては、五酸化リン、五塩化リン、塩化ホスホリル、塩化チオニル、無水酢酸、無水トリフルオロ酢酸、クロロギ酸エチル、ホスゲン等を例示することができる。これらの脱水剤は単独又は組み合わせて使用でき、さらに炭酸ナトリウム、炭酸カリウム、炭酸水素ナトリウム、炭酸水素カリウム、酢酸ナトリウム、酢酸カリウム等のアルカリ金属塩基、トリエチルアミン、トリブチルアミン、ジメチルアニリン、Ｎ-メチルモルホリン、ピリジン等の有機アミン塩基の存在下に実施することが収率の良い点で好ましい。
反応は有機溶媒中で行うことが好ましく、ベンゼン、トルエン、キシレン、ＴＨＦ、ジエチルエーテル、クロロホルム、ジクロロメタン、アセトン、エチルメチルケトン、酢酸エチル、酢酸ブチル、ＤＭＦ、ＤＭＳＯ等を用いることができる。反応は室温から溶媒還流温度から選ばれた温度で実施することができる。 Production method-5 is a method of converting the carbamoyl group of the imidazole-4-carboxamide derivative (6b) into a cyano group using a dehydrating agent.
[Production Method-5]

(In the formula, R ¹ , X and n represent the same meaning as described above.)
Examples of the dehydrating agent that can be used in this production method include phosphorus pentoxide, phosphorus pentachloride, phosphoryl chloride, thionyl chloride, acetic anhydride, trifluoroacetic anhydride, ethyl chloroformate, phosgene, and the like. These dehydrating agents can be used alone or in combination. Further, alkali metal bases such as sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, sodium acetate, potassium acetate, triethylamine, tributylamine, dimethylaniline, N-methylmorpholine In the presence of an organic amine base such as pyridine, it is preferable from the viewpoint of good yield.
The reaction is preferably performed in an organic solvent, and benzene, toluene, xylene, THF, diethyl ether, chloroform, dichloromethane, acetone, ethyl methyl ketone, ethyl acetate, butyl acetate, DMF, DMSO and the like can be used. The reaction can be carried out at a temperature selected from room temperature to the solvent reflux temperature.

  When the imidazole derivative of the present invention is used as a herbicide, the imidazole derivative of the compound of the present invention may be applied as it is, but usually an appropriate auxiliary agent is used, such as a wettable powder, granule, emulsion, flowable agent, etc. Use in form. Examples of auxiliary agents include solid carriers such as kaolin, bentonite, talc, diatomaceous earth, white carbon, and starch; water, alcohols (methanol, ethanol, propanol, butanol, ethylene glycol, etc.), and ketones (acetone, methyl ethyl ketone, cyclohexanone). Etc.), ethers (diethyl ether, 1,4-dioxane, cellosolves, etc.), aliphatic hydrocarbons (kerosene, kerosene, etc.), aromatic hydrocarbons (benzene, toluene, xylene, solvent naphtha, methylnaphthalene, etc.) ), Halogenated hydrocarbons (dichloroethane, carbon tetrachloride, trichlorobenzene, etc.), acid amides (DMF, etc.), esters (ethyl acetate, butyl acetate, fatty acid glycerin esters, etc.), nitriles (acetonitrile, etc.), etc. Solvents; nonionic Surfactant (polyoxyethylene alkyl allyl ether, polyoxyethylene sorbitan monolaurate, etc.), cationic surfactant (alkyl dimethyl benzyl ammonium chloride, alkyl pyridinium chloride, etc.), anionic surfactant (alkyl benzene sulfonate, Surfactants such as lignin sulfonate, higher alcohol sulfate, etc.) and amphoteric surfactants (alkyl dimethyl betaine, dodecylaminoethyl glycine, etc.). These solid carriers, solvents, surfactants and the like are each used as one or a mixture of two or more as required.

  For example, the herbicide containing the compound of the present invention as an active ingredient can be mixed and applied with other agricultural chemicals used in the same field, such as insecticides, fungicides, plant growth regulators and fertilizers. Moreover, the herbicidal effect can be further stabilized by mixing with one or more other herbicides. When the compound of the present invention and other herbicides are mixed and applied, the preparations of the compound of the present invention and other herbicides may be mixed at the time of application, but may be applied as a preparation containing both in advance.

  Hereinafter, although an example and a reference example explain the present invention still in detail, the present invention is not limited to these.

トリフェニルホスフィン(65.6g, 0.25mol)及びトリエチルアミン(10.1g, 0.10mmol)の四塩化炭素(60mL)溶液にトリフルオロ酢酸(11.4g, 0.10mol)を滴下添加し、氷冷下１時間撹拌した。この溶液に２,６-ジクロロアニリン(16.2g, 0.10mmol)の四塩化炭素(10mL)溶液を滴下にて加え、徐々に室温になるまで撹拌し、さらに２時間加熱還流した。反応混合物を減圧下に濃縮し、ヘキサンを加え、析出した固体をろ過により取り除き、ろ液を減圧下に濃縮した。得られた粗生成物をシリカゲルカラムクロマトグラフィー（ヘキサン）で精製することにより、Ｎ-(２,６-ジクロロフェニル)トリフルオロアセトイミドイルクロリドの淡黄色油状物(18.7g, 収率：67.7％)を得た。¹H-NMR(CDCl₃, TMS, ppm)：δ7.17(dd, J=7.5 and 7.5Hz, 1H), 7.38(d, J=7.5Hz, 2H). Reference Example-1

Trifluoroacetic acid (11.4 g, 0.10 mol) was added dropwise to a solution of triphenylphosphine (65.6 g, 0.25 mol) and triethylamine (10.1 g, 0.10 mmol) in carbon tetrachloride (60 mL), and the mixture was stirred for 1 hour under ice cooling. . To this solution was added dropwise a solution of 2,6-dichloroaniline (16.2 g, 0.10 mmol) in carbon tetrachloride (10 mL), and the mixture was gradually stirred until it reached room temperature, and further heated to reflux for 2 hours. The reaction mixture was concentrated under reduced pressure, hexane was added, the precipitated solid was removed by filtration, and the filtrate was concentrated under reduced pressure. The obtained crude product was purified by silica gel column chromatography (hexane) to give a pale yellow oily substance (18.7 g, yield: 67.7%) of N- (2,6-dichlorophenyl) trifluoroacetimidoyl chloride. Got. ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 7.17 (dd, J = 7.5 and 7.5 Hz, 1H), 7.38 (d, J = 7.5 Hz, 2H).

トリフェニルホスフィン(82.0g, 0.31mol)及びトリエチルアミン(18.9g, 0.19mmol)の四塩化炭素(105mL)溶液にジフルオロ酢酸(12.1g, 0.13mol)を滴下添加し、氷冷下１時間撹拌した。この溶液に２,６-ジクロロアニリン(20.3g, 0.13mmol)の四塩化炭素(20mL)溶液を滴下にて加え、徐々に室温になるまで撹拌し、さらに２時間加熱還流した。反応混合物を減圧下に濃縮し、ヘキサンを加え、析出した固体をろ過により取り除き、ろ液を減圧下に濃縮した。得られた粗生成物を蒸留により精製することにより、Ｎ-(２,６-ジクロロフェニル)ジフルオロアセトイミドイルクロリドの淡黄色油状物(6.2g, 収率：19.3％)を得た。¹H-NMR(CDCl₃, TMS, ppm)：δ6.38(t, J_HF=54.2Hz, 1H), 7.12(dd, J=7.7 and 8.6Hz, 1H), 7.30〜7.43(m, 2H). Reference example-2

Difluoroacetic acid (12.1 g, 0.13 mol) was added dropwise to a solution of triphenylphosphine (82.0 g, 0.31 mol) and triethylamine (18.9 g, 0.19 mmol) in carbon tetrachloride (105 mL), and the mixture was stirred for 1 hour under ice cooling. To this solution was added dropwise a solution of 2,6-dichloroaniline (20.3 g, 0.13 mmol) in carbon tetrachloride (20 mL), and the mixture was gradually stirred until it reached room temperature, and further heated under reflux for 2 hours. The reaction mixture was concentrated under reduced pressure, hexane was added, the precipitated solid was removed by filtration, and the filtrate was concentrated under reduced pressure. The obtained crude product was purified by distillation to obtain a pale yellow oily substance (6.2 g, yield: 19.3%) of N- (2,6-dichlorophenyl) difluoroacetimidoyl chloride. ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 6.38 (t, J _HF = 54.2Hz, 1H), 7.12 (dd, J = 7.7 and 8.6Hz, 1H), 7.30-7.43 (m, 2H) .

水素化ナトリウム(60％油性, 1.0g, 24.0mmol)のＴＨＦ(30mL)溶液に、イソシアノ酢酸エチル(2.5g, 22.0mmol)及びＮ-(２,６-ジクロロフェニル)トリフルオロアセトイミドイルクロリド(5.5g, 20.0mmol)のＴＨＦ(3mL)溶液を氷冷下に滴下添加し、室温下で７時間撹拌した。反応終了後、反応混合物に飽和塩化アンモニウムを加え、さらに酢酸エチルと飽和食塩水を加えて有機層を分離し、さらに水層を酢酸エチル(30mL×3)で抽出した。有機層を合わせ、無水硫酸マグネシウムで乾燥後、乾燥剤を濾過し、減圧下で溶媒を留去した。得られた残渣をシリカゲルカラムクロマトグラフィー（酢酸エチル：ヘキサン＝1：2）で精製することにより、１-(２,６-ジクロロフェニル)-５-トリフルオロメチルイミダゾール-４-カルボン酸エチルの白色固体(4.5g, 収率：63.9％)を得た。融点：101〜103℃；¹H-NMR(CDCl₃, TMS, ppm)：δ1.44(t, J=7.1Hz, 3H), 4.47(q, J=7.1Hz, 2H), 7.35〜7.60(m, 3H), 7.51(s, 1H). Reference example-3

To a solution of sodium hydride (60% oily, 1.0 g, 24.0 mmol) in THF (30 mL) was added ethyl isocyanoacetate (2.5 g, 22.0 mmol) and N- (2,6-dichlorophenyl) trifluoroacetimidoyl chloride (5.5 g, 20.0 mmol) in THF (3 mL) was added dropwise under ice cooling, and the mixture was stirred at room temperature for 7 hours. After completion of the reaction, saturated ammonium chloride was added to the reaction mixture, ethyl acetate and saturated brine were further added to separate the organic layer, and the aqueous layer was further extracted with ethyl acetate (30 mL × 3). The organic layers were combined, dried over anhydrous magnesium sulfate, the desiccant was filtered, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate: hexane = 1: 2) to give a white solid of ethyl 1- (2,6-dichlorophenyl) -5-trifluoromethylimidazole-4-carboxylate. (4.5 g, yield: 63.9%) was obtained. Melting point: 101-103 ° C; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 1.44 (t, J = 7.1 Hz, 3H), 4.47 (q, J = 7.1 Hz, 2H), 7.35-7.60 ( m, 3H), 7.51 (s, 1H).

  Reference Examples 4 to 19 were obtained in the same manner as Reference Example-3 to obtain imidazole-4-carboxylic acid ester derivatives.

Reference example-4
Compound name: ethyl 1- (2-methylphenyl) -5-trifluoromethylimidazole-4-carboxylate; yield: 23.7%; shape: white solid; melting point: 47 ° C .; ¹ H-NMR (CDCl ₃ , TMS , ppm): δ1.43 (t, J = 7.2Hz, 3H), 2.08 (s, 3H), 4.46 (q, J = 7.2Hz, 2H), 7.20-7.50 (m, 4H), 7.54 (s, 1H).

Reference Example-5
Compound name: ethyl 1- (4-t-butylphenyl) -5-trifluoromethylimidazole-4-carboxylate; yield: 71.1%; shape: pale yellow solid; melting point: 110-112 ° C .; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 1.37 (s, 9H), 1.43 (t, J = 7.2Hz, 3H), 4.45 (q, J = 7.2Hz, 2H), 7.27 (dd, J = 2.1 and 6.6Hz, 2H), 7.52 (dd, J = 2.1 and 6.6Hz, 2H), 7.62 (s, 1H).

Reference Example-6
Compound name: Ethyl 5-trifluoromethyl-1- (3-trifluoromethylphenyl) imidazole-4-carboxylate; Yield: 57.6%; Shape: light yellow solid; Melting point: 98-100 ° C .; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ1.43 (t, J = 7.3Hz, 3H), 4.45 (q, J = 7.3Hz, 2H), 7.58 (d, J = 7.9Hz, 1H), 7.60-7.80 (m, 2H), 7.67 (s, 1H), 7.85 (d, J = 7.9Hz, 1H).

Reference Example-7
Compound name: ethyl 1- (4-bromophenyl) -5-trifluoromethylimidazole-4-carboxylate; yield: 75.5%; shape: pale yellow solid; melting point: 89-90 ° C .; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ1.42 (t, J = 7.0Hz, 3H), 4.45 (q, J = 7.0Hz, 2H), 7.24 (dd, J = 2.3 and 8.8Hz, 2H), 7.61 (s , 1H), 7.67 (dd, J = 2.3 and 8.8Hz, 2H).

Reference Example-8
Compound name: ethyl 1- (2-chlorophenyl) -5-trifluoromethylimidazole-4-carboxylate; yield: 50.1%; shape: yellow solid; melting point: 77 ° C .; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ1.43 (t, J = 7.1Hz, 3H), 4.46 (q, J = 7.1Hz, 2H), 7.30-7.65 (m, 4H), 7.57 (s, 1H).

Reference Example-9
Compound name: ethyl 1- (4-chlorophenyl) -5-trifluoromethylimidazole-4-carboxylate; yield: 65.5%; shape: white solid; melting point: 110-112 ° C .; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ1.42 (t, J = 7.2Hz, 3H), 4.45 (q, J = 7.2Hz, 2H), 7.31 (dd, J = 2.1 and 6.6Hz, 2H), 7.51 (dd, J = 2.1 and 6.6Hz, 2H), 7.62 (s, 1H).

Reference Example-10
Compound name: ethyl 1- (4-nitrophenyl) -5-trifluoromethylimidazole-4-carboxylate; yield: 34.6%; shape: pale yellow solid; melting point: 147-148 ° C .; ¹ H-NMR (CDCl ₃ , TMS,
ppm): δ1.43 (t, J = 7.5Hz, 3H), 4.47 (q, J = 7.5Hz, 2H), 7.59 (dd, J = 2.5 and 7.5Hz, 2H), 7.69 (s, 1H), 8.43 (dd, J = 2.5 and 7.5Hz, 2H).

Reference Example-11
Compound name: ethyl 1- (2,6-dimethylphenyl) -5-trifluoromethylimidazole-4-carboxylate; yield: 57.1%; shape: pale yellow solid; melting point: 86 ° C .; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ1.44 (t, J = 7.2Hz, 3H), 2.03 (s, 6H), 4.46 (q, J = 7.2Hz, 2H), 7.15-7.25 (m, 2H), 7.31 (dd, J = 6.8 and 8.3Hz, 1H), 7.47 (s, 1H).

Reference Example-12
Compound name: ethyl 1- (2,4-dichlorophenyl) -5-trifluoromethylimidazole-4-carboxylate; yield: 61.2%; shape: pale yellow solid; melting point: 89-91 ° C .; ¹ H-NMR ( CDCl ₃ , TMS, ppm): δ1.43 (t, J = 7.1Hz, 3H), 4.46 (q, J = 7.1Hz, 2H), 7.36 (d, J = 8.5Hz, 1H), 7.44 (dd, J = 2.2 and 8.5Hz, 1H), 7.55 (s, 1H), 7.62 (d, J = 2.2Hz, 1H).

Reference Example-13
Compound name: ethyl 1- (3,4-dichlorophenyl) -5-trifluoromethylimidazole-4-carboxylate; yield: 61.1%; shape: pale yellow solid; melting point: 119-121 ° C .; ¹ H-NMR ( CDCl ₃ , TMS, ppm): δ1.42 (t, J = 7.2Hz, 3H), 4.45 (q, J = 7.2Hz, 2H), 7.26 (s, 1H), 7.50 (d, J = 2.5Hz, 1H), 7.63 (m, 2H).

Reference Example-14
Compound name: ethyl 1- (4-chloro-2-fluorophenyl) -5-trifluoromethylimidazole-4-carboxylate; yield: 72.1%; shape: pale yellow solid; melting point: 120-121 ° C .; ¹ H -NMR (CDCl ₃ , TMS, ppm): δ1.43 (t, J = 7.0Hz, 3H), 4.45 (q, J = 7.0Hz, 2H), 7.25-7.40 (m, 3H), 7.59 (s, 1H).

Reference Example-15
Compound name: ethyl 1- (2,6-difluorophenyl) -5-trifluoromethylimidazole-4-carboxylate; yield: 54.3%; shape: white solid; melting point: 99-100 ° C .; ¹ H-NMR ( CDCl ₃ , TMS, ppm): δ1.43 (t, J = 7.1Hz, 3H), 4.46 (q, J = 7.1Hz, 2H), 7.14 (ddd, J = 1.5 and 8.6Hz, J _HF = 8.6Hz , 2H), 7.48 to 7.58 (m, 1H), 7.61 (s, 1H).

Reference Example-16
Compound name: ethyl 1- (2,6-dichloro-4-trifluoromethylphenyl) -5-trifluoromethylimidazole-4-carboxylate; yield: 44.7%; shape: pale yellow solid; melting point: 108-110 ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 1.44 (t, J = 7.1 Hz, 3H), 4.47 (q, J = 7.1 Hz, 2H), 7.52 (s, 1H), 7.79 ( s, 2H).

Reference Example-17
Compound name: 1- (4-chloro-5-cyclopentyloxy-2-fluorophenyl) -5-trifluoromethylimidazole-4-carboxylate; yield: 42.5%; shape: pale yellow solid; melting point: 102- 103 ° C; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ1.43 (t, J = 7.2 Hz, 3H), 1.60 to 1.70 (m, 3H), 1.80 to 1.95 (m, 5H), 4.45 ( q, J = 7.2Hz, 2H), 4.65 to 4.80 (m, 1H), 6.88 (d, J _HF = 6.6Hz, 1H), 7.34 (d, J _HF = 8.8Hz, 1H), 7.62 (s, 1H ).

Reference Example-18
Compound name: 1- (4-chloro-2-fluoro-5-propargyloxyphenyl) -5-trifluoromethylimidazole-4-carboxylate; yield: 51.2%; shape: light brown solid; melting point: 131- 133 ° C; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ1.43 (t, J = 7.3 Hz, 3H), 2.59 (t, J = 2.5 Hz, 1H), 4.45 (q, J = 7.3 Hz , 2H), 4.80 (d, J = 2.5Hz, 2H), 7.12 (d, J _HF = 6.5Hz, 1H), 7.39 (d, J _HF = 8.5Hz, 1H), 7.62 (s, 1H).

Reference Example-19
Compound name: ethyl 1- (2,6-dichlorophenyl) -5-difluoromethylimidazole-4-carboxylate; yield: 72.7%; shape: pale yellow solid; melting point: 121-122 ° C .; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 1.46 (t, J = 7.1Hz, 3H), 4.47 (q, J = 7.1Hz, 2H), 7.35-7.55 (m, 4H), 7.50 (t,
(J _HF = 52.6Hz, 1H).

１-(２,６-ジクロロフェニル)-５-トリフルオロメチルイミダゾール-４-カルボン酸エチル(3.3g, 9.5mmol)のエタノール(30mL)溶液に５％水酸化カリウム水溶液(16mL)を加え、室温で２.５時間撹拌した。反応終了後、エタノールを減圧留去し、得られた混合物を氷冷下２Ｎ-塩酸に加えた。析出した固体をろ過し、ヘキサンで洗浄することにより、１-(２,６-ジクロロフェニル)-５-トリフルオロメチルイミダゾール-４-カルボン酸の白色固体(3.0g, 収率：98.4％)を得た。融点：201〜202℃；¹H-NMR(DMSO, DMSO-d₆, ppm)：δ7.70(dd, J=6.9 and 9.2Hz, 1H), 7.81(d, J=9.2Hz, 1H), 7.81(d, J=6.9Hz, 1H), 8.31(s, 1H), 13.52(br s, 1H). Example-1

To a solution of ethyl 1- (2,6-dichlorophenyl) -5-trifluoromethylimidazole-4-carboxylate (3.3 g, 9.5 mmol) in ethanol (30 mL) was added 5% aqueous potassium hydroxide (16 mL) at room temperature. Stir for 2.5 hours. After completion of the reaction, ethanol was distilled off under reduced pressure, and the resulting mixture was added to 2N hydrochloric acid under ice cooling. The precipitated solid was filtered and washed with hexane to obtain a white solid (3.0 g, yield: 98.4%) of 1- (2,6-dichlorophenyl) -5-trifluoromethylimidazole-4-carboxylic acid. It was. Melting point: 201-202 ° C .; ¹ H-NMR (DMSO, DMSO-d ₆ , ppm): δ 7.70 (dd, J = 6.9 and 9.2 Hz, 1H), 7.81 (d, J = 9.2 Hz, 1H), 7.81 (d, J = 6.9Hz, 1H), 8.31 (s, 1H), 13.52 (br s, 1H).

  In Examples 2 to 17, imidazole-4-carboxylic acid derivatives were obtained in the same manner as Example 1.

Example-2
Compound name: 1- (2-methylphenyl) -5-trifluoromethylimidazole-4-carboxylic acid; yield: 84.4%; shape: white solid; melting point: 166-167 ° C .; 1H-NMR spectrum (DMSO-d ₆ , DMSO, ppm): δ2.02 (s, 3H), 7.30-7.55 (m, 4H), 8.12 (s, 1H), 13.30 (br s, 1H).

Example-3
Compound name: 1- (4-t-butylphenyl) -5-trifluoromethylimidazole-4-carboxylic acid; Yield: 93.0%; Shape: white solid; Melting point: 179-181 ° C .; 1H-NMR spectrum (DMSO -d ₆ , DMSO, ppm): δ1.33 (s, 9H), 7.45 (d, J = 8.4Hz, 2H), 7.60 (d, J = 8.4Hz, 2H), 8.13 (s, 1H). The proton of the carboxy group could not be assigned.)

Example-4
Compound name: 5-trifluoromethyl-1- (3-trifluoromethylphenyl) imidazole-4-carboxylic acid; yield: 98.5%; shape: white solid; melting point: 180-182 ° C; 1H-NMR spectrum (DMSO -d ₆ , DMSO, ppm): δ 7.80 to 8.00 (m, 2H), 8.00 (d, J = 7.5Hz, 1H), 8.09 (br s, 1H), 8.25 (s, 1H), 13.36 (br s, 1H).

Example-5
Compound name: 1- (4-bromophenyl) -5-trifluoromethylimidazole-4-carboxylic acid; yield: 81.1%; shape: white solid; melting point: 190-191 ° C .; ¹ H-NMR (DMSO-d ₆ , DMSO, ppm): δ7.54 (d, J = 8.8Hz, 2H), 7.80 (d, J = 8.8Hz, 2H), 8.17 (s, 1H). (Proton of carboxy group could not be assigned) .)

Example-6
Compound name: 1- (2-chlorophenyl) -5-trifluoromethylimidazole-4-carboxylic acid; Yield: 86.2%; Shape: white solid; Melting point: 170-171 ° C .; ¹ H-NMR (DMSO-d ₆ , DMSO, ppm): δ 7.45-7.70 (m, 2H), 7.70-7.85 (m, 2H), 8.02 (s, 1H). (Carboxy group proton could not be assigned.)

Example-7
Compound name: 1- (4-chlorophenyl) -5-trifluoromethylimidazole-4-carboxylic acid; Yield: 89.4%; Shape: white solid; Melting point: 183-184 ° C .; ¹ H-NMR (DMSO-d ₆ , DMSO, ppm): δ7.61 (d, J = 8.8Hz, 2H), 7.68 (d, J = 8.8Hz, 2H), 8.18 (s, 1H), 13.3 (br s, 1H).

Example-8
Compound name: 1- (4-nitrophenyl) -5-trifluoromethylimidazole-4-carboxylic acid; yield: 87.2%; shape: white solid; melting point: 166-167 ° C .; ¹ H-NMR (DMSO-d ₆ , DMSO, ppm): δ 7.89 (dd, J = 2.1 and 6.8Hz, 2H), 8.28 (s, 1H), 8.44 (dd, J = 2.1and 6.8Hz, 2H). Could not be attributed.)

Example-9
Compound name: 1- (2,6-dimethylphenyl) -5-trifluoromethylimidazole-4-carboxylic acid; yield: 90.5%; shape: white solid; melting point:> 270 ° C .; ¹ H-NMR (DMSO- _{d 6, DMSO, ppm):} δ1.97 (s, 6H), 7.29 (d, J = 6.3Hz, 1H), 7.29 (d, J = 8.6Hz, 1H), 7.41 (d, J = 8.6Hz, 1H), 7.42 (d, J = 6.3 Hz, 1H), 8.05 (s, 1H). (The proton of the carboxy group could not be assigned.)

Example-10
Compound name: 1- (2,4-dichlorophenyl) -5-trifluoromethylimidazole-4-carboxylic acid; yield: 83.2%; shape: white solid; melting point:> 270 ° C .; ¹ H-NMR (DMSO-d ₆ , DMSO, ppm): δ 7.67 (dd, J = 2.3 and 8.5Hz, 1H), 7.78 (d, J = 8.5Hz, 1H), 7.98 (d, J = 2.3Hz, 1H), 8.03 (s , 1H). (The proton of the carboxy group could not be assigned.)

Example-11
Compound name: 1- (4-Chloro-2-fluorophenyl) -5-trifluoromethylimidazole-4-carboxylic acid; Yield: 98.3%; Shape: white solid; Melting point: 170-172 ° C .; ¹ H-NMR (DMSO-d ₆ , DMSO, ppm): δ 7.45-7.65 (m, 1H), 7.79-7.88 (m, 2H), 8.23 (s, 1H). (Proton of carboxy group could not be assigned.)

Example-12
Compound name: 1- (2,6-difluorophenyl) -5-trifluoromethylimidazole-4-carboxylic acid; yield: 94.1%; shape: white solid; melting point: 180 ° C .; ¹ H-NMR (DMSO-d ₆ , DMSO, ppm): δ 7.40-7.60 (m, 2H), 7.69-7.84 (m, 1H), 8.37 (s, 1H). (The proton of the carboxy group could not be assigned.)

Example-13
Compound name: 1- (2,6-dichloro-4-trifluoromethylphenyl) -5-trifluoromethylimidazole-4-carboxylic acid; yield:>98%; shape: white solid; melting point:> 260 ° C .; ¹ H-NMR (DMSO-d ₆ , DMSO, ppm): δ8.16 (s, 1H), 8.34 (s, 2H). (The proton of the carboxy group could not be assigned.)

Example-14
Compound name: 1- (2,6-Dichloro-4-trifluoromethoxyphenyl) -5-trifluoromethylimidazole-4-carboxylic acid; Yield: 92.2%; Shape: white solid; Melting point: 181-182 ° C .; ¹ H-NMR (DMSO-d ₆ , DMSO, ppm): δ 8.07 (q, J _HF = 0.7 Hz, 2H), 8.32 (s, 1H), 13.55 (br s, 1H).

Example-15
Compound name: 1- (4-chloro-5-cyclopentyloxy-2-fluorophenyl) -5-trifluoromethylimidazole-4-carboxylic acid; yield: 98.3%; shape: white solid; melting point: 166 ° C .; ¹ H-NMR (DMSO-d ₆ , DMSO, ppm): δ 1.59-1.89 (m, 8H), 4.92 (m, 1H), 6.67 (d, J _HF = 7.0Hz, 1H), 7.82 (d, J _HF = 9.3Hz, 1H), 8.25 (s, 1H). (The proton of the carboxy group could not be assigned.)

Example-16
Compound name: 1- (4-chloro-2-fluoro-5-propargyloxyphenyl) -5-trifluoromethylimidazole-4-carboxylic acid; yield: 89.0%; shape: light brown solid; melting point: 152-153 ¹ H-NMR (DMSO-d ₆ , DMSO, ppm): δ 3.67 (t, J = 2.5 Hz, 1H), 4.95 (d, J = 2.5 Hz, 2H), 7.73 (d, J _HF = 7.5Hz, 1H), 7.90 (d, J _HF = 10.0Hz, 1H), 8.23 (s, 1H). (The proton of the carboxy group could not be assigned.)

Example-17
Compound name: 1- (2,6-dichlorophenyl) -5-difluoromethylimidazole-4-carboxylic acid; yield:>98%; shape: white solid; melting point: 260 ° C .; ¹ H-NMR (DMSO-d ₆ , DMSO, ppm): δ7.63 ( dd, J = 9.3Hz, 1H), 7.70~7.80 (m, 2H), 7.75 (t, J HF = 52.5Hz, 1H), 7.99 (s, 1H) (. The proton of the carboxy group could not be assigned.)

１-(２,６-ジクロロフェニル)-５-トリフルオロメチルイミダゾール-４-カルボン酸エチル(1.0g, 2.8mmol)のメタノール(7mL)溶液に、40％メチルアミンメタノール溶液(1mL)を加え、この溶液を室温で１５時間撹拌した。反応終了後、溶媒を減圧下で留去し、得られた残渣をシリカゲルカラムクロマトグラフィー（酢酸エチル：ヘキサン＝1：1）で精製することにより、Ｎ-メチル-１-(２,６-ジクロロフェニル)-５-トリフルオロメチルイミダゾール-４-カルボキサミドの淡黄色固体(0.7g, 収率：72.6％)を得た。融点：116〜118℃；¹H-NMR(CDCl₃, TMS, ppm)：δ3.02(d, J=5.0Hz, 3H), 7.20〜7.38(m, 1H), 7.40(s, 1H), 7.45〜7.60(m, 3H). Example-18

To a solution of ethyl 1- (2,6-dichlorophenyl) -5-trifluoromethylimidazole-4-carboxylate (1.0 g, 2.8 mmol) in methanol (7 mL) was added 40% methylamine methanol solution (1 mL). The solution was stirred at room temperature for 15 hours. After completion of the reaction, the solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography (ethyl acetate: hexane = 1: 1) to give N-methyl-1- (2,6-dichlorophenyl). ) -5-trifluoromethylimidazole-4-carboxamide was obtained as a pale yellow solid (0.7 g, yield: 72.6%). Melting point: 116-118 ° C .; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ3.02 (d, J = 5.0 Hz, 3H), 7.20-7.38 (m, 1H), 7.40 (s, 1H), 7.45-7.60 (m, 3H).

  In Examples -19 to 34, N-methylimidazole-4-carboxamide derivatives were obtained in the same manner as Example -18.

Example-19
Compound name: N-methyl-1- (2-methylphenyl) -5-trifluoromethylimidazole-4-carboxamide; Yield:>98%; Shape: white solid; Melting point: 161-162 ° C .; ¹ H-NMR (DMSO-d ₆ , DMSO, ppm): δ 2.07 (s, 3H), 3.02 (d, J = 5.1 Hz, 3H), 7.20-7.50 (m, 5H), 7.42 (s, 1H).

Example-20
Compound Name: N- methyl -1- (4-t- butylphenyl) -5-trifluoromethyl-imidazole-4-carboxamide; Yield: 77.1%; Morphology: white solid; mp: 154 to 156 ° C.; ¹ H- NMR (DMSO-d ₆ , DMSO, ppm): δ 1.37 (s, 9H), 3.01 (d, J = 5.0Hz, 3H), 7.20-7.30 (m, 3H), 7.50 (s, 1H), 7.51 (dd, J = 2.0 and 6.6Hz, 2H).

Example-21
Compound name: N-methyl-1- (4-bromophenyl) -5-trifluoromethylimidazole-4-carboxamide; Yield: 75.0%; Shape: pale yellow solid; Melting point: 198-199 ° C .; ¹ H-NMR (DMSO-d ₆ , DMSO, ppm): δ3.01 (d, J = 5.0Hz, 3H), 7.22-7.24 (m, 1H), 7.24 (dd, J = 2.5 and 7.5Hz, 2H), 7.50 ( s, 1H), 7.66 (dd, J = 2.5 and 7.5Hz, 2H).

Example-22
Compound name: N-methyl-1- (2-chlorophenyl) -5-trifluoromethylimidazole-4-carboxamide; Yield: 87.5%; Shape: white solid; Melting point: 152 ° C .; ¹ H-NMR (DMSO-d ₆ , DMSO, ppm): δ3.02 (d, J = 5.0Hz, 3H), 7.20-7.30 (m, 1H), 7.35-7.65 (m, 5H).

Example-23
Compound name: N-methyl-1- (4-chlorophenyl) -5-trifluoromethylimidazole-4-carboxamide; Yield: 83.3%; Shape: white solid; Melting point: 196-197 ° C .; ¹ H-NMR (DMSO -d ₆ , DMSO, ppm): δ3.01 (d, J = 5.0Hz, 3H), 7.15-7.30 (m, 1H), 7.31 (dd, J = 2.1 and 6.6Hz, 2H), 7.50 (s, 1H), 7.50 (dd, J = 2.1 and 6.6Hz, 2H).

Example-24
Compound name: N-methyl-1- (4-nitrophenyl) -5-trifluoromethylimidazole-4-carboxamide; Yield: 60.7%; Shape: white solid; Melting point: 245-246 ° C .; ¹ H-NMR ( DMSO-d ₆ , DMSO, ppm): δ3.02 (d, J = 5.0Hz, 3H), 7.15-7.30 (m, 1H), 7.51 (s, 1H), 7.58 (dd, J = 2.5 and 7.5Hz , 2H), 8.42 (dd, J = 2.5 and 7.5Hz, 2H).

Example-25
Compound name: N-methyl-1- (2,6-dimethylphenyl) -5-trifluoromethylimidazole-4-carboxamide; Yield: 80.6%; Shape: white solid; Melting point: 190-192 ° C .; ¹ H- NMR (DMSO-d ₆ , DMSO, ppm): δ 2.20 (s, 6H), 3.30 (d, J = 5.0 Hz, 3H), 7.10-7.45 (m, 5H).

Example-26
Compound name: N-methyl-1- (2,4-dichlorophenyl) -5-trifluoromethylimidazole-4-carboxamide; Yield: 95.6%; Shape: white solid; Melting point: 154-155 ° C .; ¹ H-NMR (DMSO-d ₆ , DMSO, ppm): δ3.02 (d, J = 5.0Hz, 3H), 7.25-7.31 (m, 1H), 7.35 (d, J = 7.5Hz, 1H), 7.43 (dd, J = 2.5 and 7.5Hz, 1H), 7.44 (s, 1H), 7.60 (d, J = 2.5Hz, 1H).

Example-27
Compound name: N-methyl-1- (3,4-dichlorophenyl) -5-trifluoromethylimidazole-4-carboxamide; Yield: 62.5%; Shape: white solid; Melting point: 189-190 ° C .; ¹ H-NMR (DMSO-d ₆ , DMSO, ppm): δ3.01 (d, J = 5.0Hz, 3H), 7.23 (dd, J = 2.5 and 8.6Hz, 1H), 7.26 (s, 1H), 7.45-7.60 ( m, 1H), 7.49 (d, J = 2.5Hz, 1H), 7.61 (d, J = 8.6Hz, 1H).

Example-28
Compound name: N-methyl-1- (4-chloro-2-fluorophenyl) -5-trifluoromethylimidazole-4-carboxamide; yield: 99.5%; shape: white solid; melting point: 143-145 ° C .; ¹ H-NMR (DMSO-d ₆ , DMSO, ppm): δ3.01 (d, J = 5.0 Hz, 3H), 7.10-7.36 (m, 4H), 7.48 (s, 1H).

Example-29
Compound name: N-methyl-1- (2,6-difluorophenyl) -5-trifluoromethylimidazole-4-carboxamide; Yield: 89.3%; Shape: pale yellow solid; Melting point: 155-157 ° C .; ¹ H _{-NMR (DMSO-d 6, DMSO} , ppm): δ3.02 (d, J = 5.1Hz, 3H), 7.13 (ddd, J = 1.5 and 8.6Hz, J HF = 8.6Hz, 2H), 7.20~7.35 (m, 1H), 7.46-7.60 (m, 1H), 7.49 (s, 1H).

Example-30
Compound name: N-methyl-1- (2,6-dichloro-4-trifluoromethylphenyl) -5-trifluoromethylimidazole-4-carboxamide; Yield: Shape: white solid; Melting point: 98.5%; ¹ H-NMR (DMSO-d ₆ , DMSO, ppm): δ3.03 (d, J = 5.0 Hz, 3H), 7.24-7.29 (m, 1H), 7.40 (s, 1H), 7.79 ( s, 2H).

Example-31
Compound name: N-methyl-1- (4-chloro-5-cyclopentyloxy-2-fluorophenyl) -5-trifluoromethylimidazole-4-carboxamide; yield: 97.0%; shape: white solid; melting point: 124 ˜126 ° C .; ¹ H-NMR (DMSO-d ₆ , DMSO, ppm): δ 1.64 to 1.67 (m, 3H), 1.87 to 1.89 (m, 5H), 3.01 (d, J = 5.0 Hz, 3H) , 4.72 ~ 4.74 (m, 1H), 6.87 (d, J _HF = 7.5Hz, 1H), 7.15 ~ 7.30 (m, 1H), 7.33 (d, J _HF = 10.0Hz, 1H), 7.51 (s, 1H ).

Example-32
Compound name: N-methyl-1- (4-chloro-2-fluoro-5-propargyloxyphenyl) -5-trifluoromethylimidazole-4-carboxamide; yield: 55.9%; shape: white solid; melting point: 116 ˜118 ° C .; ¹ H-NMR (DMSO-d ₆ , DMSO, ppm): δ 2.59 (t, J = 2.4 Hz, 1H), 3.01 (d, J = 5.0 Hz, 3H), 4.79 (d, J = 2.4Hz, 2H), 7.11 (d, J _HF = 6.5Hz, 1H), 7.20-7.35 (m, 1H), 7.38 (d, J _HF = 8.7Hz, 1H), 7.51 (s, 1H).

Example-33
Compound name: N-methyl-1- (2,6-dichlorophenyl) -5-difluoromethylimidazole-4-carboxamide; Yield: 84.2%; Shape: white solid; Melting point: 223-224 ° C .; ¹ H-NMR ( DMSO-d ₆ , DMSO, ppm): δ3.02 (d, J = 5.0Hz, 3H), 7.21 ~ 7.30 (m, 1H), 7.38 ~ 7.55 (m, 4H), 7.72 (t, J _HF = 52.8 Hz, 1H).

Example-34 JST-10045T
Compound name: N-methyl-1- (2,6-dichlorophenyl) -5-pentafluoroethylimidazole-4-carboxamide; Yield: 75.6%; Shape: white solid; Melting point: 127-129 ° C; ¹ H- NMR (CDCl ₃ , TMS, ppm): δ 3.01 (d, J = 5.1 Hz, 3H), 7.30-7.40 (m, 1H), 7.40-7.59 (m, 4H).

１-(２,６-ジクロロフェニル)-５-トリフルオロメチルイミダゾール-４-カルボン酸(0.25g, 0.77mmol)のトルエン(20mL)溶液に、塩化チオニル(1.6mL)を加え、この溶液を120℃で２時間加熱還流した後、オイルバスの温度を160℃まで昇温し、ディーン・スタークを用いてトルエン及び過剰の塩化チオニルを除去した。次いで反応混合物を室温まで冷却した後、ジクロロメタン(5mL)を加え、さらに氷冷下でトリエチルアミン(0.1mL, 0.92mmol)とｔ-ブチルアミン(0.1mL, 0.92mmol)を加え、徐々に室温まで昇温させ、そのままの温度で１時間撹拌した。反応終了後、ジクロロメタンを減圧下で留去し、得られた混合物に弱酸性になるまで２Ｎ-塩酸を加え、酢酸エチル(10mL×3)で抽出した。有機層を合わせ無水硫酸マグネシウムで乾燥し、乾燥剤をろ過後、溶媒を減圧下で留去した。得られた残渣をシリカゲルカラムクロマトグラフィー（酢酸エチル：ヘキサン＝1：1）で精製することにより、Ｎ-ｔ-ブチル-１-(２,６-ジクロロフェニル)-５-トリフルオロメチルイミダゾール-４-カルボキサミドの白色固体(0.25g, 収率：86.2％)を得た。融点：157〜159℃；¹H-NMR(CDCl₃, TMS, ppm)：δ1.50(s, 9H), 7.18〜7.24(m, 1H), 7.42〜7.56(m, 4H). Example-35

To a solution of 1- (2,6-dichlorophenyl) -5-trifluoromethylimidazole-4-carboxylic acid (0.25 g, 0.77 mmol) in toluene (20 mL) was added thionyl chloride (1.6 mL). Then, the temperature of the oil bath was raised to 160 ° C., and toluene and excess thionyl chloride were removed using Dean Stark. Next, the reaction mixture was cooled to room temperature, dichloromethane (5 mL) was added, and triethylamine (0.1 mL, 0.92 mmol) and t-butylamine (0.1 mL, 0.92 mmol) were added under ice cooling, and the temperature was gradually raised to room temperature. And stirred for 1 hour at the same temperature. After completion of the reaction, dichloromethane was distilled off under reduced pressure, 2N-hydrochloric acid was added to the resulting mixture until it became weakly acidic, and the mixture was extracted with ethyl acetate (10 mL × 3). The organic layers were combined and dried over anhydrous magnesium sulfate, the desiccant was filtered off, and the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate: hexane = 1: 1) to give Nt-butyl-1- (2,6-dichlorophenyl) -5-trifluoromethylimidazole-4- A white solid of carboxamide (0.25 g, yield: 86.2%) was obtained. Melting point: 157 to 159 ° C; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 1.50 (s, 9H), 7.18 to 7.24 (m, 1H), 7.42 to 7.56 (m, 4H).

  In Examples 36 to 175, imidazole-4-carboxamide derivatives were obtained in the same manner as Example 35.

Example-36
Compound name: N- (t-butyl) -1- (2-methylphenyl) -5-trifluoromethylimidazole-4-carboxamide; Yield: 71.4%; Shape: yellow viscous substance; ¹ H-NMR ( CDCl ₃ , TMS, ppm): δ 1.50 (s, 9H), 2.08 (s, 3H), 7.17 (br s, 1H), 7.40 (s, 1H), 7.20-7.50 (m, 4H).

Example-37
Compound name: N-propargyl-1- (2-methylphenyl) -5-trifluoromethylimidazole-4-carboxamide; Yield: 56.5%; Shape: pale yellow solid; Melting point: 102-103 ° C .; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 2.07 (s, 3H), 2.27 (t, J = 2.5Hz, 1H), 4.27 (dd, J = 2.5 and 5.6Hz, 2H), 7.20-7.60 (m, 6H).

Example-38
Compound name: N, N-tetramethylene-1- (2-methylphenyl) -5-trifluoromethylimidazole-4-carboxamide; Yield: 43.3%; Shape: white solid; Melting point: 137-139 ° C .; ¹ H -NMR (CDCl ₃ , TMS, ppm): δ 1.90 to 2.00 (m, 4H), 2.10 (s, 3H), 3.45 to 3.60 (m, 2H), 3.60 to 3.73 (m, 2H), 7.20 to 7.50 (m, 4H), 7.52 (s, 1H).

Example-39
Compound name: N- (2,4-difluorophenyl) -1- (3-trifluoromethylphenyl) -5-trifluoromethylimidazole-4-carboxamide; Yield: 45.9%; Shape: white solid; Melting point: 204 ˜205 ° C .; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 6.89 to 6.96 (m, 2H), 7.58 to 7.75 (m, 3H), 7.65 (s, 1H), 7.85 to 7.88 (m, 1H), 8.43-8.56 (m, 1H), 9.34 (s, 1H).

Example-40
Compound name: Nt-butyl-1- (2-chlorophenyl) -5-trifluoromethylimidazole-4-carboxamide; Yield: 73.1%; Shape: pale yellow solid; Melting point: 83-85 ° C .; ¹ H- NMR (CDCl ₃ , TMS, ppm): δ 1.49 (s, 9H), 7.17 (br s, 1H), 7.35-7.60 (m, 4H), 7.44 (s, 1H).

Example-41
Compound name: N, N-tetramethylene-1- (2-chlorophenyl) -5-trifluoromethyl-imidazole-4-carboxamide; yield 64.0%; Morphology: white solid; mp: 146~147 ℃; ¹ H- NMR (CDCl ₃ , TMS, ppm): δ 1.85 to 2.05 (m, 4H), 3.30 to 3.73 (m, 4H), 7.40 to 7.65 (m, 5H).

Example-42
Compound name: N-ethyl-N-cyclohexyl-1- (2-chlorophenyl) -5-trifluoromethylimidazole-4-carboxamide; Yield: 37.5%; Shape: white solid; Melting point: 147-148 ° C .; ¹ H -NMR (CDCl ₃ , TMS, ppm): δ 0.95 to 1.35 (m, 3H), 1.12 and 1.27 (each t, J = 7.1 and 7.1 Hz, total 3H), 1.35 to 2.00 (m, 7H), 3.10 ~ 3.35 and 3.35 ~ 3.65 (each m, total 2H), 3.35 ~ 3.65 and 4.30 ~ 4.50 (each, m, total 1H), 7.40 ~ 7.65 (m, 5H).

Example-43
Compound name: N-ethyl-N-phenyl-1- (2-chlorophenyl) -5-trifluoromethylimidazole-4-carboxamide; Yield: 31.3%; Shape: white solid; Melting point: 115 ° C .; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 1.26 (t, J = 7.1 Hz, 3H), 4.01 (q, J = 7.1 Hz, 2H), 7.05 to 7.85 (m, 10H).

Example-44
Compound name: N- (4-fluorophenyl) -N-isopropyl-1- (2-chlorophenyl) -5-trifluoromethylimidazole-4-carboxamide; Yield: 45.0%; Shape: white solid; Melting point: 138- 140 ° C; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 1.20 (d, J = 6.8 Hz, 6H), 5.15 (sept, J = 6.8 Hz, 1H), 6.85 to 7.05 (m, 2H) , 7.05-7.20 (m, 2H), 7.25-7.65 (m, 4H), 7.33 (s, 1H).

Example-45
Compound name: N-ethyl-1- (4-bromophenyl) -5-trifluoromethylimidazole-4-carboxamide; Yield: 28.1%; Shape: white solid; Melting point: 149-150 ° C .; ¹ H-NMR ( CDCl ₃ , TMS, ppm): δ 1.26 (t, J = 7.5Hz, 3H), 3.05 to 3.14 (m, 2H), 7.10 to 7.25 (m, 1H), 7.23 (d, J = 8.8Hz, 2H ), 7.50 (s, 1H), 7.66 (d, J = 8.8Hz, 2H).

Example-46
Compound name: N-isopropyl-1- (4-bromophenyl) -5-trifluoromethylimidazole-4-carboxamide; Yield: 68.8%; Shape: white solid; Melting point: 189-190 ° C .; ¹ H-NMR ( CDCl ₃ , TMS, ppm): δ 1.27 (d, J = 6.8Hz, 6H), 4.18 ~ 4.33 (m, 1H), 7.01 ~ 7.10 (m, 1H), 7.24 (d, J = 8.5Hz, 2H ), 7.50 (s, 1H), 7.65 (d, J = 8.5Hz, 2H).

Example-47
Compound name: N-ethyl-N-cyclohexyl-1- (4-bromophenyl) -5-trifluoromethylimidazole-4-carboxamide; Yield: 31.3%; Shape: white solid; Melting point: 118 ° C .; ¹ H- NMR (CDCl ₃ , TMS, ppm): δ 1.00 to 1.30 (m, 3H), 1.30 to 2.00 (m, 7H), 1.13 and 1.27 (each t, J = 7.1 and 7.1Hz, total 3H), 3.33 and 3.48 (each q, J = 7.1 and 7.1Hz, total 2H), 3.39 to 3.54 and 4.26 to 4.44 (each m, total 1H), 7.29 and 7.30 (each d, J = 8.7 and 8.7Hz, total 2H), 7.61 and 7.62 (each s, total 1H), 7.66 and 7.67 (each d, J = 8.7 and 8.7Hz, total 2H).

Example-48
Compound name: N-ethyl-N-phenyl-1- (4-bromophenyl) -5-trifluoromethylimidazole-4-carboxamide; Yield: 62.7%; Shape: light brown solid; Melting point: 113 ° C .; ¹ H -NMR (CDCl ₃ , TMS, ppm): δ1.25 (t, J = 7.1Hz, 3H), 3.99 (q, J = 7.1Hz, 2H), 7.03 (d, J = 8.5Hz, 2H), 7.10 ~ 7.35 (m, 4H), 7.38 (s, 1H), 7.57 (d, J = 8.5Hz, 2H), 7.60 ~ 7.75 (m, 1H).

Example-49
Compound name: N-cyclopropyl-1- (4-chlorophenyl) -5-trifluoromethylimidazole-4-carboxamide; yield: 97.8%; shape: white solid; melting point: 152-154 ° C .; ¹ H-NMR ( CDCl ₃ , TMS, ppm): δ 0.61 to 0.68 (m, 2H), 0.82 to 0.90 (m, 2H), 2.88 to 2.97 (m, 1H), 7.20 to 7.35 (m, 3H), 7.45 to 7.55 ( m, 2H), 7.48 (s, 1H).

Example-50
Compound name: N-isopropyl-1- (4-chlorophenyl) -5-trifluoromethylimidazole-4-carboxamide; Yield: 70.6%; Shape: white solid; Melting point: 163-165 ° C .; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 1.27 (d, J = 6.5Hz, 6H), 4.21 to 4.38 (m, 1H), 7.01 to 7.10 (m, 1H), 7.28 (d, J = 7.5Hz, 2H) , 7.48 (s, 1H), 7.59 (d, J = 7.5Hz, 2H).

Example-51
Compound name: N-neopentyl-1- (4-chlorophenyl) -5-trifluoromethylimidazole-4-carboxamide; Yield: 64.5%; Shape: white solid; Melting point: 152-153 ° C .; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ0.99 (s, 9H), 3.26 (d, J = 6.6Hz, 2H), 7.27-7.33 (m, 1H), 7.30 (dd, J = 2.0 and 6.7Hz, 2H) , 7.51 (dd, J = 2.0 and 6.7Hz, 2H), 7.52 (s, 1H).

Example-52
Compound name: N- (2,4-difluorophenyl) -1- (4-chlorophenyl) -5-trifluoromethylimidazole-4-carboxamide; Yield: 62.1%; Shape: white solid; Melting point: 171-172 ° C. ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 6.85-6.95 (m, 2H), 7.33 (dd, J = 2.5 and 7.5 Hz, 2H), 7.53 (dd, J = 2.5 and 7.5 Hz, 2H), 7.59 (s, 1H), 8.50 (ddd, J = 6.0Hz, J _HF = 9.3 and 9.3Hz, 1H), 9.33 (br s, 1H).

Example-53
Compound name: Nt-butyl-1- (2,6-dimethylphenyl) -5-trifluoromethylimidazole-4-carboxamide; Yield: 54.2%; Shape: white solid; Melting point: 102-104 ° C .; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 1.50 (s, 9H), 2.02 (s, 6H), 7.10-7.23 (m, 3H), 7.25-7.35 (m, 2H).

Example-54
Compound name: N- (4-t-butylphenyl) -1- (2,6-dimethylphenyl) -5-trifluoromethylimidazole-4-carboxamide; Yield: 33.3%; Shape: yellow solid; Melting point: 198 ¹ H-NMR (CDCl ₃ , TMS, ppm): δ1.33 (s, 9H), 2.05 (s, 6H), 7.10-7.20 (m, 2H), 7.25-7.45 (m, 4H), 7.66 (d, J = 2.0 and 6.7Hz, 2H), 9.14 (br s, 1H).

Example-55
Compound name: N-ethyl-N-phenyl-1- (2,6-dimethylphenyl) -5-trifluoromethylimidazole-4-carboxamide; Yield: 25.8%; Shape: white solid; Melting point: 127-128 ° C. ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 1.26 (t, J = 7.2Hz, 3H), 1.72 (s, 3H), 2.74 (s, 3H), 4.00 (q, J = 7.2Hz , 2H), 7.00 to 7.15 (d, J = 7.6Hz, 2H), 7.15 to 7.25 (m, 7H).

Example-56
Compound name: N- (4-Fluorophenyl) -N-isopropyl-1- (2,6-dimethylphenyl) -5-trifluoromethylimidazole-4-carboxamide; Yield: 7.0%; Shape: White solid; Melting point : 164 to 165 ° C; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 1.13 (t, J = 6.8 Hz, 6H), 1.64 (s, 6H), 5.08 (sept, J = 6.8 Hz, 1H ), 6.80-6.90 (m, 2H), 7.00-7.25 (m, 5H), 7.10 (s, 1H).

Example-57
Compound name: N- (2,4-Difluorophenyl) -N-isopropyl-1- (2,6-dimethylphenyl) -5-trifluoromethylimidazole-4-carboxamide; Yield: 19.4%; Shape: White solid Melting point: 152 ° C .; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 1.17 (dd, J = 2.2 and 6.8 Hz, 3H), 1.27 (d, J = 6.8 Hz, 3H), 1.75 (s , 3H), 1.79 (s, 3H), 5.11 (sept, J = 6.8Hz, 1H), 6.70-6.85 (m, 2H), 7.11 (d, J = 7.6Hz, 2H), 7.11 (s, 1H) , 7.18-7.30 (m, 2H).

Example-58
Compound name: N, N-dimethyl-1- (2,4-dichlorophenyl) -5-trifluoromethylimidazole-4-carboxamide; Yield: 30.9%; Shape: white solid; Melting point: 185-187 ° C .; ¹ H -NMR (CDCl ₃ , TMS, ppm): δ 3.05 (s, 3H), 3.14 (s, 3H), 7.35-7.50 (m, 2H), 7.55-7.65 (m, 2H).

Example-59
Compound name: N-ethyl-1- (2,4-dichlorophenyl) -5-trifluoromethylimidazole-4-carboxamide; Yield: 55.8%; Shape: white solid; Melting point: 135-137 ° C .; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 1.27 (t, J = 7.5Hz, 3H), 3.51 (dq, J = 5.0 and 7.5Hz, 2H), 7.24-7.31 (m, 1H), 7.34 (d, J = 10.0Hz, 1H), 7.42 (dd, J = 2.5 and 10.0Hz, 1H), 7.44 (s, 1H), 7.61 (d, J = 2.5Hz, 1H).

Example-60
Compound name: N-propyl-1- (2,4-dichlorophenyl) -5-trifluoromethylimidazole-4-carboxamide; yield: 19.9%; shape: white solid; melting point: 135-137 ° C .; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ1.00 (t, J = 7.5Hz, 3H), 1.55-1.70 (m, 2H), 3.43 (dt, J = 6.3 and 7.4Hz, 2H), 7.24-7.52 ( m, 1H), 7.34 (d, J = 8.5Hz, 1H), 7.42 (dd, J = 2.2 and 8.5Hz, 1H), 7.44 (s, 1H), 7.60 (d, J = 2.2Hz, 1H).

Example-61
Compound name: N-isopropyl-1- (2,4-dichlorophenyl) -5-trifluoromethylimidazole-4-carboxamide; Yield: 59.2%; Shape: white solid; Melting point: 135-137 ° C .; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 1.28 (d, J = 5.0Hz, 6H), 4.20 to 4.34 (m, 1H), 7.01 to 7.11 (m, 1H), 7.34 (d, J = 8.5Hz, 1H), 7.42 (dd, J = 2.2 and 8.5Hz, 1H), 7.44 (s, 1H), 7.61 (d, J = 2.2Hz, 1H).

Example-62
Compound name: N-isobutyl-1- (2,4-dichlorophenyl) -5-trifluoromethylimidazole-4-carboxamide; Yield: 52.1%; Shape: white solid; Melting point: 148-150 ° C .; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ0.99 (d, J = 6.7Hz, 6H), 1.83 to 2.05 (m, 1H), 3.29 (dd, J = 6.5 and 6.6Hz, 2H), 7.25 to 7.40 ( m, 1H), 7.35 (d, J = 8.5Hz, 1H), 7.44 (dd, J = 2.2 and 8.5Hz, 1H), 7.45 (s, 1H), 7.61 (d, J = 2.2Hz, 1H).

Example-63
Compound name: N-s-butyl-1- (2,4-dichlorophenyl) -5-trifluoromethylimidazole-4-carboxamide; yield: 84.8%; shape: white solid; melting point: 122-124 ° C .; ¹ H -NMR (CDCl ₃ , TMS, ppm): δ 0.97 and 0.98 (each t, J = 7.4 and 7.4 Hz, total 3H), 1.24 and 1.25 (each d, J = 6.5 and 6.5 Hz, total 3H), 1.54 ~ 1.63 (m, 2H), 4.00 ~ 4.25 (m, 1H), 7.00 ~ 7.15 (m, 1H), 7.33 and 7.34 (each d, J = 8.5 and 8.5Hz, total 1H), 7.42 (dd, J = 2.0 and 8.5Hz, 1H), 7.44 (s, 1H), 7.60 (d, J = 2.0Hz, 1H).

Example-64
Compound name: N-hexyl-1- (2,4-dichlorophenyl) -5-trifluoromethylimidazole-4-carboxamide; Yield: 65.7%; Shape: white solid; Melting point: 118-119 ° C .; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ0.90 (t, J = 5.0Hz, 3H), 1.29 to 1.43 (m, 6H), 1.54 to 1.66 (m, 2H), 3.41 to 3.49 (dt, J = 5.0 and 7.5Hz, 2H), 7.26-7.44 (m, 1H), 7.34 (d, J = 7.5Hz, 1H), 7.42 (dd, J = 2.5 and 7.5Hz, 1H), 7.44 (s, 1H), 7.60 (d, J = 2.5Hz, 1H).

Example-65
Compound name: N-tetrahydrofurfuryl-1- (2,4-dichlorophenyl) -5-trifluoromethylimidazole-4-carboxamide; Yield: 38.0%; Shape: white solid; Melting point: 130-132 ° C .; ¹ H -NMR (CDCl ₃ , TMS, ppm): δ 1.55 to 1.75 (m, 1H), 1.90 to 2.05 (m, 3H), 3.40 to 3.48 (m, 1H), 3.80 to 4.12 (m, 4H), 7.33 (d, J = 7.5Hz, 1H), 7.42 (dd, J = 2.5 and 7.5Hz, 1H), 7.44 (s, 1H), 7.57-7.59 (m, 1H), 7.60 (d, J = 2.5Hz, 1H).

Example-66
Compound name: N-cyclopropyl-1- (2,4-dichlorophenyl) -5-trifluoromethylimidazole-4-carboxamide; yield: 66.2%; shape: white solid; melting point: 134-135 ° C .; ¹ H- NMR (CDCl ₃ , TMS, ppm): δ 0.63 to 0.69 (m, 2H), 0.83 to 0.89 (m, 2H), 2.87 to 2.95 (m, 1H), 7.25 to 7.40 (m, 1H), 7.34 ( d, J = 8.5Hz, 1H), 7.42 (dd, J = 2.2 and 8.5Hz, 1H), 7.42 (s, 1H), 7.60 (d,
J = 2.2Hz, 1H).

Example-67
Compound Name: N- propargyl-1 (2,4-dichlorophenyl) -5-trifluoromethyl-imidazole-4-carboxamide; Yield: 69.6%; Morphology: pale yellow solid; mp: 137-138 ° C.; ¹ H- NMR (CDCl ₃ , TMS, ppm): δ 2.27 (t, J = 2.5Hz, 1H), 4.26 (dd, J = 2.5 and 5.0Hz, 2H), 7.35 (d, J = 8.5Hz, 1H),
7.40-7.50 (m, 1H), 7.43 (dd, J = 2.2 and 8.5Hz, 1H), 7.46 (s, 1H), 7.60 (d, J = 2.2Hz,
1H).

Example-68
Compound name: N- (4-t-butylbenzyl) -1- (2,4-dichlorophenyl) -5-trifluoromethylimidazole-4-carboxamide; Yield: 69.1%; Shape: white solid; Melting point: 179- 180 ° C; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ1.32 (s, 9H), 4.62 (d, J = 5.9 Hz, 2H), 7.30-7.45 (m, 7H), 7.46-7.55 ( m, 1H), 7.61 (d, J = 2.3Hz, 1H).

Example-69
Compound name: N- (4-fluorophenyl) -1- (2,4-dichlorophenyl) -5-trifluoromethylimidazole-4-carboxamide; Yield: 75.1%; Shape: pale yellow solid; Melting point: 170-172 ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 7.03 to 7.15 (m, 2H), 7.38 (d, J = 8.5Hz, 1H), 7.45 (dd, J = 2.2 and 8.5Hz, 1H ), 7.51 (s, 1H), 7.63 (d, J = 2.2Hz, 1H), 7.65-7.75 (m, 2H), 9.13 (br s, 1H).

Example-70
Compound name: N-ethyl-1- (2,6-dichlorophenyl) -5-trifluoromethylimidazole-4-carboxamide; Yield: 43.7%; Shape: white solid; Melting point: 183-185 ° C .; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 1.28 (t, J = 7.3Hz, 3H), 3.51 (dq, J = 6.0 and 7.3Hz, 2H), 7.26-7.36 (m, 1H), 7.40 (s, 1H), 7.44-7.53 (m, 3H).

Example-71
Compound name: N-propyl-1- (2,6-dichlorophenyl) -5-trifluoromethylimidazole-4-carboxamide; Yield: 78.2%; Shape: white solid; Melting point: 183-185 ° C .; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ1.01 (t, J = 7.3Hz, 3H), 1.67 (tq, J = 7.3 and 7.3Hz, 2H), 3.43 (dt, J = 6.2 and 7.3Hz, 2H) , 7.29-7.39 (m, 1H), 7.40 (s, 1H), 7.44-7.60 (m, 3H).

Example-72
Compound name: N-isopropyl-1- (2,6-dichlorophenyl) -5-trifluoromethylimidazole-4-carboxamide; Yield: 58.2%; Shape: white solid; Melting point: 158-159 ° C .; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 1.29 (t, J = 6.6Hz, 6H), 4.30 (d sept, J = 5.0 and 6.6Hz, 1H), 7.12 (br d, J = 5.0Hz, 1H) , 7.40 (s, 1H), 7.44-7.55 (m, 3H).

Example-73
Compound name: N-s-butyl-1- (2,6-dichlorophenyl) -5-trifluoromethylimidazole-4-carboxamide; yield: 68.4%; shape: white solid; melting point: 93-94 ° C .; ¹ H -NMR (CDCl ₃ , TMS, ppm): δ0.99 (t, J = 7.5Hz, 3H), 1.26 (d, J = 6.6Hz, 3H), 1.40-1.75 (m, 2H), 4.00-4.25 ( m, 1H), 7.00-7.20 (m, 1H), 7.40 (s, 1H), 7.40-7.55 (m, 3H).

Example-74
Compound name: N-neopentyl-1- (2,6-dichlorophenyl) -5-trifluoromethylimidazole-4-carboxamide; Yield: 39.0%; Shape: white solid; Melting point: 190-191 ° C .; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ1.01 (s, 9H), 3.27 (d, J = 6.6Hz, 2H), 7.30-7.45 (m, 1H), 7.41 (s, 1H), 7.43-7.55 ( m, 3H).

Example-75
Compound name: Nt-amyl-1- (2,6-dichlorophenyl) -5-trifluoromethylimidazole-4-carboxamide; yield: 83.4%; shape: white solid; melting point: 151-152 ° C .; ¹ H -NMR (CDCl ₃ , TMS, ppm): δ0.95 (t, J = 7.6Hz, 3H), 1.45 (s, 6H), 1.86 (q, J = 7.6Hz, 2H), 7.11 (br s, 1H ), 7.38 (s, 1H), 7.40-7.55 (m, 3H).

Example-76
Compound name: N-hexyl-1- (2,6-dichlorophenyl) -5-trifluoromethylimidazole-4-carboxamide; yield: 63.9%; shape: white solid; melting point: 169-171 ° C .; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ0.90 (t, J = 6.6Hz, 3H), 1.23-1.48 (m, 6H), 1.48-1.70 (m, 2H), 3.45 (dt, J = 6.5and 6.9 Hz, 2H), 7.20-7.35 (m, 1H), 7.35-7.70 (m, 4H).

Example-77
Compound name: N- (2,2,2-trifluoroethyl) -1- (2,6-dichlorophenyl) -5-trifluoromethylimidazole-4-carboxamide; Yield: 80.3%; Shape: white solid; melting point : 119 to 120 ° C .; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ4.12 (dq, J = 6.7 Hz, J _HF = 9.0 Hz, 2H), 7.42 to 7.56 (m, 3H), 7.45 ( s, 1H), 7.57-7.66 (m, 1H).

Example-78
Compound name: N- (4-t-butylbenzyl) -1- (2,6-dichlorophenyl) -5-trifluoromethylimidazole-4-carboxamide; Yield: 57.1%; Shape: white solid; Melting point: 161- 163 ° C; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ1.32 (s, 9H), 4.62 (d, J = 5.9Hz, 2H), 7.34 (dd, J = 2.3 and 6.3Hz, 2H) , 7.30-7.55 (m, 6H), 7.38 (s, 1H).

Example-79
Compound name: N- (α-phenethyl) -1- (2,6-dichlorophenyl) -5-trifluoromethylimidazole-4-carboxamide; Yield: 77.8%; Shape: white solid; Melting point: 171-173 ° C .; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 1.63 (d, J = 6.9 Hz, 3H), 5.34 (dq, J = 6.9 and 6.9 Hz, 1H), 7.20-7.60 (m, 10H).

Example-80
Compound name: N-cumyl-1- (2,6-dichlorophenyl) -5-trifluoromethylimidazole-4-carboxamide; Yield: 80.1%; Shape: white solid; Melting point: 189-190 ° C .; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 1.87 (s, 6H), 7.20 to 7.55 (m, 9H), 7.63 (br s, 1H).

Example-81
Compound name: N-cyclohexyl-1- (2,6-dichlorophenyl) -5-trifluoromethylimidazole-4-carboxamide; yield: 63.9%; shape: white solid; melting point: 81-83 ° C .; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 1.13 to 1.52 (m, 5H), 1.61 to 1.84 (m, 3H), 1.98 to 2.10 (m, 2H), 3.91 to 4.05 (m, 1H), 7.05 to 7.25 (m, 1H), 7.40 (s, 1H), 7.40-7.65 (m, 3H).

Example-82
Compound name: N- (1-adamantyl) -1- (2,6-dichlorophenyl) -5-trifluoromethylimidazole-4-carboxamide; Yield: 24.7%; Shape: white solid; Melting point:> 240 ° C .; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 1.65 to 1.80 (m, 6H), 2.05 to 2.20 (m, 9H), 7.08 (br s, 1H), 7.38 (s, 1H), 7.39 to 7.55 (m, 3H).

Example-83
Compound Name: N- propargyl-1 (2,6-dichlorophenyl) -5-trifluoromethyl-imidazole-4-carboxamide; Yield: 71.9%; Morphology: pale yellow solid; mp: 130 to 132 ° C.; ¹ H- NMR (CDCl ₃ , TMS, ppm): δ 2.28 (t, J = 2.5 Hz, 1H), 4.27 (dd, J = 2.5 and 5.5 Hz, 2H), 7.40-7.60 (m, 5H).

Example-84
Compound name: N- (2-fluorophenyl) -1- (2,6-dichlorophenyl) -5-trifluoromethylimidazole-4-carboxamide; Yield: 44.5%; Shape: white solid; Melting point: 158-159 ° C. ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 7.03 to 7.22 (m, 3H), 7.45 to 7.58 (m, 4H), 8.50 to 8.65 (m, 1H), 9.50 (br s, 1H) .

Example-85
Compound name: N- (2,4-difluorophenyl) -1- (2,6-dichlorophenyl) -5-trifluoromethylimidazole-4-carboxamide; Yield: 35.4%; Shape: white solid; Melting point: 221-1 223 ° C .; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 6.80-6.98 (m, 2H), 7.40-7.46 (m, 4H), 8.40-8.60 (m, 1H), 9.37 (br s, 1H).

Example-86
Compound name: N- (2,4,6-trimethylphenyl) -1- (2,6-dichlorophenyl) -5-trifluoromethylimidazole-4-carboxamide; Yield: 53.0%; Shape: pale yellow solid; Melting point : 224 to 226 ° C; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 2.30 (s, 9H), 6.93 (s, 2H), 7.40 to 7.57 (m, 4H), 8.54 (br s, 1H ).

Example-87
Compound name: N-ethoxy-1- (2,6-dichlorophenyl) -5-trifluoromethylimidazole-4-carboxamide; Yield: 52.7%; Shape: white solid; Melting point: 151-153 ° C .; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ1.36 (t, J = 7.0Hz, 3H), 4.14 (q, J = 7.0Hz, 2H), 7.40-7.55 (m, 3H), 7.42 (s, 1H) , 8.18 (br s, 1H).

Example-88
Compound name: Nt-butyloxy-1- (2,6-dichlorophenyl) -5-trifluoromethylimidazole-4-carboxamide; Yield: 32.2%; Shape: white solid; Melting point: 194-195 ° C .; ¹ H -NMR (CDCl ₃ , TMS, ppm): δ 1.38 (s, 9H), 7.42 (s, 1H), 7.44-7.55 (m, 3H), 9.20 (br s, 1H).

Example-89
Compound name: N, N-diisopropyl-1- (2,6-dichlorophenyl) -5-trifluoromethylimidazole-4-carboxamide; Yield: 31.1%; Shape: white solid; Melting point: 116-117 ° C .; ¹ H -NMR (CDCl ₃ , TMS, ppm): δ1.21 (d, J = 6.7Hz, 6H), 1.55 (d, J = 6.8Hz, 6H), 3.55 (sept, J = 6.8Hz, 1H), 3.87 (sept, J = 6.7Hz, 1H), 7.40-7.60 (m, 4H).

Example-90
Compound name: N-ethyl-N-cyclohexyl-1- (2,6-dichlorophenyl) -5-trifluoromethylimidazole-4-carboxamide; yield: 32.3%; shape: white solid; melting point: 122-123 ° C .; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 1.10 and 1.27 (each t, J = 7.2 and 7.2 Hz, total 3H), 0.95 to 1.20 (m, 3H), 1.35 to 1.70 (m, 3H) , 1.70 ~ 1.95 (m, 4H), 3.35 and 3.48 (each q, J = 7.1 and 7.1Hz, total 2H), 3.35 ~ 3.55 and 4.25 ~ 4.50 (each m, 1H), 7.40 ~ 7.60 (m, 4H) .

Example-91
Compound name: N- (4-fluorophenyl) -N-isopropyl-1- (2,6-dichlorophenyl) -5-trifluoromethylimidazole-4-carboxamide; Yield: 57.0%; Shape: white solid; Melting point: 168-170 ° C; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 1.20 (d, J = 6.8 Hz, 6H), 5.14 (sept, J = 6.8 Hz, 1H), 6.90-7.05 (m, 2H), 7.10-7.20 (m, 2H), 7.23 (s, 1H), 7.35-7.47 (m, 3H).

Example-92
Compound name: N- (2,4-difluorophenyl) -N-isopropyl-1- (2,6-dichlorophenyl) -5-trifluoromethylimidazole-4-carboxamide; Yield: 17.9%; Shape: white solid; Melting point: 141-143 ° C .; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 1.17 (dd, J = 2.2 and 6.8 Hz, 3H), 1.26 (d, J = 6.7 Hz, 3H), 5.11 ( sept, J = 6.8Hz, 1H), 6.77 (m, 2H), 7.20 (s, 1H), 7.38-7.67 (m, 4H).

Example-93
Compound name: N-propyl-1- (4-chloro-2-fluorophenyl) -5-trifluoromethylimidazole-4-carboxamide; Yield: 89.3%; Shape: white solid; Melting point: 92-93 ° C .; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ1.00 (t, J = 7.5Hz, 3H), 1.56-1.72 (m, 2H), 3.41 (dt, J = 7.3 and 7.3Hz, 2H), 7.15 ~ 7.25 (m, 1H), 7.26 ~ 7.34 (m, 3H), 7.48 (s, 1H).

Example-94
Compound name: N-isopropyl-1- (2,6-difluorophenyl) -5-trifluoromethylimidazole-4-carboxamide; Yield: 71.4%; Shape: pale yellow solid; Melting point: 108-109 ° C .; ¹ H -NMR (CDCl ₃ , TMS, ppm): δ 1.28 (d, J = 6.6 Hz, 6H), 4.29 (dq, J = 5.0 and 6.6 Hz, 1H), 7.05 to 7.15 (m, 1H), 7.13 ( ddd, J = 1.5 and 8.6Hz, J _HF = 8.6Hz, 2H), 7.45-7.63 (m, 1H), 7.49 (s, 1H).

Example-95
Compound name: N-s-butyl-1- (2,6-difluorophenyl) -5-trifluoromethylimidazole-4-carboxamide; Yield: 67.3%; Shape: white solid; Melting point: 88 ° C .; ¹ H- NMR (CDCl ₃ , TMS, ppm): δ 0.98 (t, J = 7.5Hz, 3H), 1.25 (d, J = 6.6Hz, 3H), 1.50 to 1.70 (m, 2H), 4.00 to 4.20 (m , 1H), 7.00-7.20 (m, 3H), 7.45-7.65 (m, 2H).

Example-96
Compound name: Nt-butyl-1- (2,6-difluorophenyl) -5-trifluoromethylimidazole-4-carboxamide; Yield: 67.3%; Shape: white solid; Melting point: 84 ° C .; ¹ H- NMR (CDCl ₃ , TMS, ppm): δ 1.49 (s, 9H), 7.12 (ddd, J = 1.4 and 8.6Hz, J _HF = 7.6Hz, 2H), 7.05 to 7.20 (m, 1H), 7.47 ( s, 1H), 7.43-7.64 (m, 1H).

Example-97
Compound name: N-cyanomethyl-1- (2,6-difluorophenyl) -5-trifluoromethylimidazole-4-carboxamide; Yield: 78.0%; Shape: white solid; Melting point: 161-163 ° C .; ¹ H- NMR (CDCl ₃ , TMS, ppm): δ 4.40 (d, J = 6.1 Hz, 2H), 7.09-7.20 (m, 2H), 7.49-7.70 (m, 2H), 7.54 (s, 1H).

Example-98
Compound name: 2-[[1- (2,6-Difluorophenyl) -5-trifluoromethylimidazol-4-yl] carbonylamino] -3-methylbutanoate; Yield: 78.7%; Shape: white solid; Melting point: 103-105 ° C .; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ1.02 (d, J = 6.9 Hz, 3H), 1.04 (d, J = 6.8 Hz, 3H), 2.20-2.39 ( m, 1H), 3.78 (s, 3H), 4.74 (dd, J = 4.9 and 9.2Hz, 1H), 7.05-7.20 (m, 2H), 7.45-7.60 (m, 2H), 7.77 (br d, J = 9.2Hz, 1H).

Example-99
Compound name: N- (2-fluorophenyl) -1- (2,6-difluorophenyl) -5-trifluoromethylimidazole-4-carboxamide; Yield: 69.0%; Shape: white solid; Melting point: 157-159 ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 7.04 to 7.22 (m, 5H), 7.50 to 7.63 (m, 1H), 7.58 (s, 1H), 8.45 to 8.60 (m, 1H) , 9.47 (br s, 1H).

Example-100
Compound name: Nt-butyl-1- (2,6-dichloro-4-trifluoromethylphenyl) -5-trifluoromethylimidazole-4-carboxamide; yield: 55.6%; shape: white solid; melting point: 149-151 ° C .; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ1.50 (s, 9H), 7.18 (br s, 1H), 7.39 (s, 1H), 7.78 (s, 2H).

Example-101
Compound name: N-propargyl-1- (2,6-dichloro-4-trifluoromethoxyphenyl) -5-trifluoromethylimidazole-4-carboxamide; yield: 47.1%; shape: white solid; melting point: 142- 144 ° C; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 2.29 (t, J = 2.6 Hz, 1H), 4.28 (dd, J = 2.6 and 5.5 Hz, 2H), 7.40-7.50 (m, 1H), 7.43 (s, 1H), 7.79 (s, 2H).

Example-102
Compound name: N-ethyl-1- (2,6-dichlorophenyl) -5-difluoromethylimidazole-4-carboxamide; yield: 72.0%; shape: white solid; melting point: 195-197 ° C .; ¹ H-NMR ( CDCl ₃ , TMS, ppm): δ 1.28 (t, J = 7.3Hz, 3H), 3.50 (dq, J = 5.9 and 7.3Hz, 2H), 7.20-7.36 (m, 1H), 7.36-7.54 (m , 3H), 7.41 (s, 1H), 7.72 (t, J _HF = 52.8Hz, 1H).

Example-103
Compound name: Nt-butyl-1- (2,6-dichlorophenyl) -5-difluoromethylimidazole-4-carboxamide; yield: 48.2%; shape: white solid; melting point: 169-170 ° C .; ¹ H- NMR (CDCl ₃ , TMS, ppm): δ 1.50 (s, 9H), 7.20 (br s, 1H), 7.35 to 7.55 (m, 4H), 7.71 (t, J _HF = 52.9Hz, 1H).

Example-104
Compound name: N-ethoxy-1- (2,6-dichlorophenyl) -5-difluoromethylimidazole-4-carboxamide; Yield: 71.7%; Shape: white solid; Melting point: 210-211 ° C .; ¹ H-NMR ( CDCl ₃ , TMS, ppm): δ 1.37 (t, J = 7.1Hz, 3H), 4.13 (q, J = 7.1Hz, 2H), 7.35-7.55 (m, 4H), 7.64 (t, J _HF = 52.7Hz, 1H), 9.62 (br s, 1H).

Example-105
Compound name: Nt-butyloxy-1- (2,6-dichlorophenyl) -5-difluoromethylimidazole-4-carboxamide; Yield: 17.5%; Shape: white solid; Melting point: 225-227 ° C .; ¹ H- NMR (CDCl ₃ , TMS, ppm): δ 1.38 (s, 9H), 7.38-7.55 (m, 3H), 7.49 (s, 1H), 7.65 (t, J _HF = 52.7Hz, 1H), 9.23 ( br s, 1H).

Example-106
Compound name: N- (4-fluorophenyl) -N-isopropyl-1- (2,6-dichlorophenyl) -5-difluoromethylimidazole-4-carboxamide; yield: 42.0%; shape: white solid; melting point: 165 ˜167 ° C .; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 1.21 (d, J = 6.8 Hz, 6H), 5.00 to 5.20 (m, 1H), 6.85 to 7.20 (m, 5H), 7.30 ~ 7.50 (m, 4H).

Example-107
Compound name: N- (2,4-difluorophenyl) -N-isopropyl-1- (2,6-dichlorophenyl) -5-difluoromethylimidazole-4-carboxamide; yield: 40.2%; shape: white solid; melting point : 167-168 ° C; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 1.15 (dd, J = 2.0 and 6.7 Hz, 3H), 1.27 (d, J = 6.9 Hz, 3H), 4.95-5.15 (m, 1H), 6.70-6.90 (m, 2H), 7.00-7.10 (m, 1H), 7.10-7.30 (m, 2H), 7.30-7.50 (m, 3H).

Example-108
Compound name: Nt-butyl-N-ethyl-1- (2-methylphenyl) -5-trifluoromethylimidazole-4-carboxamide; Yield: 28.3%; Shape: white solid; Melting point: 135-137 ° C. ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 1.15 (t, J = 7.1 Hz, 3H), 1.57 (s, 9H), 1.58 (s, 3H), 3.30 to 3.65 (m, 2H) , 7.35-7.65 (m, 4H), 7.54 (s, 1H).

Example-109
Compound name: Nt-butyl-1- (2-t-butylphenyl) -5-trifluoromethylimidazole-4-carboxamide; Yield: 84.4%; Shape: white solid; Melting point: 119-121 ° C .; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 1.18 (s, 3H), 1.20 (s, 9H), 1.50 (s, 9H), 7.01 (dd, J = 6.4 and 7.8Hz, 1H), 7.04 (br s, 1H), 7.20-7.33 (m, 1H), 7.40-7.55 (m, 2H), 7.60-7.66 (m, 1H).

Example-110
Compound name: Nt-butyl-N-ethyl-1- (2-t-butylphenyl) -5-trifluoromethylimidazole-4-carboxamide; yield: 39.0%; shape: white solid; melting point: 133- 134 ° C; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 1.12 (t, J = 7.1 Hz, 3H), 1.20 (s, 9H), 1.57 (s, 9H), 3.30 to 3.65 (m, 2H), 7.00 to 7.10 (m, 1H), 7.20 to 7.33 (m, 1H), 7.40 to 7.53 (m, 1H), 7.57 (s, 1H), 7.64 (dd, J = 1.4 and 8.2Hz, 1H) .

Example-111
Compound name: Nt-butyl-N-isopropyl-1- (2-t-butylphenyl) -5-trifluoromethylimidazole-4-carboxamide; Yield: 29.3%; Shape: white solid; Melting point: 128- 130 ° C; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ1.22 (s, 9H), 1.42 (d, J = 7.0Hz, 3H), 1.43 (d, J = 6.9Hz, 3H), 1.51 (s, 9H), 3.90 to 4.15 (m, 1H), 7.05 to 7.15 (m, 1H), 7.20 to 7.33 (m, 1H), 10.87 (dt, J = 1.5 and 7.3Hz, 1H), 7.56 (s , 1H), 7.64 (dd, J = 1.5 and 7.5Hz, 1H).

Example-112
Compound name: Nt-butyl-1- (2-ethyl-6-methylphenyl) -5-trifluoromethylimidazole-4-carboxamide; Yield: 9.4%; Shape: white solid; Melting point: 131-133 ° C. ¹ H-NMR (CDCl ₃ , TMS, ppm): δ1.12 (t, J = 7.6 Hz, 3H), 1.51 (s, 9H), 2.01 (s, 3H), 2.10 to 2.45 (m, 2H) , 7.10-7.25 (m, 3H), 7.30-7.40 (m, 1H), 7.34 (s, 1H).

Example-113
Compound name: Nt-butyl-N-ethyl-1- (2-ethyl-6-methylphenyl) -5-trifluoromethylimidazole-4-carboxamide; Yield: 26.2%; Shape: colorless oily substance; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 1.14 (t, J = 7.6 Hz, 3H), 1.14 (t, J = 7.1 Hz, 3H), 1.57 (s, 9H), 2.03 (s, 3H), 2.15 to 2.45 (m, 2H), 3.48 (q, J = 7.1Hz, 2H), 7.15 to 7.25 (m, 2H), 7.30 to 7.45 (m, 1H), 7.44 (s, 1H).

Example-114
Compound name: Nt-butyl-N-ethyl-1- (2,6-diethylphenyl) -5-trifluoromethylimidazole-4-carboxamide; Yield: 10.5%; Shape: colorless oil; ¹ H- NMR (CDCl ₃ , TMS, ppm): δ 1.14 (t, J = 7.6Hz, 6H), 1.15 (t, J = 7.0Hz, 3H), 1.57 (s, 9H), 2.10-2.45 (m, 1H ), 3.48 (q, J = 7.1Hz, 2H), 7.24 (d, J = 7.7Hz, 2H), 7.35-7.50 (m, 1H), 7.44 (s, 1H).

Example-115
Compound name: Nt-butyl-1- (2-biphenyl) -5-trifluoromethylimidazole-4-carboxamide; yield: 23.7%; shape: white solid; melting point: 159-161 ° C .; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 1.45 (s, 9H), 7.05 (br s, 1H), 7.05 to 7.15 (m, 1H), 7.19 (s, 1H), 7.25 to 7.40 (m, 4H) , 7.40-7.65 (m, 4H).

Example-116
Compound name: Nt-butyl-N-ethyl-1- (2-biphenyl) -5-trifluoromethylimidazole-4-carboxamide; Yield: 26.1%; Shape: colorless oil; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ1.01 (t, J = 7.1Hz, 3H), 1.53 (s, 9H), 3.05 to 3.50 (m, 2H), 7.05 to 7.20 (m, 2H), 7.22 (s, 1H), 7.23-7.30 (m, 3H), 7.45-7.65 (m, 4H).

Example-117
Compound name: Nt-butyl-1- (2-trifluoromethylphenyl) -5-trifluoromethylimidazole-4-carboxamide; Yield: 56.2%; Shape: white solid; Melting point: 124-125 ° C .; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 1.50 (s, 9H), 7.17 (br s, 1H), 7.35-7.45 (m, 1H), 7.47 (s, 1H), 7.65-7.80 (m , 2H), 7.80-7.95 (m, 1H).

Example-118
Compound name: Nt-butyl-N-isopropyl-1- (2-trifluoromethylphenyl) -5-trifluoromethylimidazole-4-carboxamide; Yield: 30.1%; Shape: white solid; Melting point: 122- 124 ° C; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 1.35 to 1.50 (m, 6H), 1.46 (s, 9H), 3.80 to 4.05 (sept, J = 6.9 Hz, 1H), 7.45 to 7.60 (m, 2H), 7.65-7.78 (m, 2H), 7.80-7.90 (m, 1H).

Example-119
Compound name: Nt-butyl-1- (2-bromophenyl) -5-trifluoromethylimidazole-4-carboxamide; Yield: 64.9%; Shape: white solid; Melting point: 100-1O2 ° C .; ¹ H- NMR (CDCl ₃ , TMS, ppm): δ 1.50 (s, 9H), 7.18 (br s, 1H), 7.35 to 7.55 (m, 4H), 7.75 (dd, J = 1.4 and 7.2Hz, 1H).

Example-120
Compound name: Nt-butyl-N-ethyl-1- (2-bromophenyl) -5-trifluoromethylimidazole-4-carboxamide; Yield: 59.9%; Shape: white solid; Melting point: 125-127 ° C. ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 1.15 (t, J = 7.1 Hz, 3H), 1.57 (s, 9H), 3.30 to 3.65 (m, 2H), 7.35 to 7.50 (m, 3H), 7.54 (s, 1H), 7.70-7.80 (m, 1H).

Example-121
Compound name: Nt-butyl-N-ethyl-1- (4-bromophenyl) -5-trifluoromethylimidazole-4-carboxamide; yield: 64.6%; shape: white solid; melting point: 166-167 ° C. ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 1.16 (t, J = 7.1 Hz, 3H), 1.56 (s, 9H), 3.45 (q, J = 7.1 Hz, 2H), 7.24 to 7.33 (m, 2H), 7.58 (s, 1H), 7.60-7.70 (m, 2H).

Example-122
Compound name: Nt-butyl-N-ethyl-1- (2-chlorophenyl) -5-trifluoromethylimidazole-4-carboxamide; yield: 92.7%; shape: white solid; melting point: 162-164 ° C .; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 1.15 (t, J = 7.1Hz, 3H), 1.57 (s, 9H), 3.40 to 3.55 (m, 2H), 7.25 to 7.40 (m, 3H ), 7.40-7.48 (m, 1H), 7.50 (s, 1H).

Example-123
Compound name: Nt-butyl-1- (2,6-dibromophenyl) -5-trifluoromethylimidazole-4-carboxamide; Yield: 72.5%; Shape: pale yellow solid; Melting point: 209-211 ° C .; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ1.50 (s, 9H), 7.21 (br s, 1H), 7.24-7.34 (m, 1H), 7.38 (s, 1H), 7.71 (d, J = 8.1Hz, 2H).

Example-124
Compound name: Nt-butyl-N-ethyl-1- (2,6-dibromophenyl) -5-trifluoromethylimidazole-4-carboxamide; yield: 67.0%; shape: white solid; melting point: 162- 164 ° C; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 1.14 (t, J = 7.1 Hz, 3H), 1.57 (s, 9H), 3.48 (q, 2H), 7.23 to 7.34 (m, 1H), 7.48 (s, 1H), 7.72 (d, J = 8.1Hz, 2H).

Example-125
Compound name: Nt-butyl-N-isopropyl-1- (2,6-dibromophenyl) -5-trifluoromethylimidazole-4-carboxamide; yield: 39.1%; shape: white solid; melting point: 148- 150 ° C; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 1.45 (d, J = 7.0 Hz, 6H), 1.48 (s, 9H), 3.85 to 4.05 (m, 1H), 7.20 to 7.34 ( m, 1H), 7.45 (s, 1H), 7.71 (d, J = 8.1Hz, 2H).

Example-126
Compound name: Nt-butyl-1- (2,3-dichlorophenyl) -5-trifluoromethylimidazole-4-carboxamide; Yield: 59.6%; Shape: pale yellow solid; Melting point: 158-159 ° C .; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 1.49 (s, 9H), 7.16 (br s, 1H), 7.31 (dd, J = 1.9 and 7.8Hz, 1H), 7.38 (dd, J = 7.8 and 7.8Hz, 1H), 7.44 (s, 1H), 7.67 (dd, J = 1.9 and 7.8Hz, 1H).

Example-127
Compound name: N- (3-cyano-3-pentyl) -1- (2,4-dichlorophenyl) -5-trifluoromethylimidazole-4-carboxamide; Yield: 50.8%; Shape: white solid; Melting point: 128 ˜130 ° C .; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 1.13 (t, J = 7.4 Hz, 6H), 2.00 to 2.30 (m, 4H), 7.30 to 7.40 (m, 2H), 7.40 ~ 7.50 (m, 2H), 7.62 (d, J = 1.9Hz, 1H).

Example-128
Compound name: N, N-diisopropyl-1- (2,4-dichlorophenyl) -5-trifluoromethylimidazole-4-carboxamide; Yield: 63.7%; Shape: white solid; Melting point: 182-183 ° C; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 1.10-1.30 (m, 6H), 1.54 (d, J = 6.8Hz, 6H), 3.56 (sept, J = 6.8Hz, 1H), 3.86 (sept , J = 6.7Hz, 1H), 7.40-7.45 (m, 2H), 7.54 (s, 1H), 7.55-7.65 (m, 1H).

Example-129
Compound name: Nt-butyl-N-ethyl-1- (2,4-dichlorophenyl) -5-trifluoromethylimidazole-4-carboxamide; Yield: 39.8%; Shape: white solid; Melting point: 162-163 ° C; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 1.14 (t, J = 7.1 Hz, 3H), 1.56 (s, 9H), 3.25 to 3.60 (m, 2H), 7.35 to 7.45 ( m, 2H), 7.53 (s, 1H), 7.55 to 7.65 (m, 1H).

Example-130
Compound name: Ns-butyl-N-propyl-1- (2,4-dichlorophenyl) -5-trifluoromethylimidazole-4-carboxamide; Yield: 30.8%; Shape: white solid; Melting point: 95 ° C. ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 0.60 to 1.08 (m, 6H), 1.10 to 1.35 (m, 3H), 1.35 to 1.90 (m, 4H), 2.90 to 3.25 and 3.25 to 3.55 (each m, total 2H), 3.55 to 3.80 and 4.25 to 4.50 (each m, total 1H), 7.40 to 7.45 (m, 2H), 7.55 (s, 1H), 7.55 to 7.65 (m, 1H).

Example-131
Compound name: N, N-di-s-butyl-1- (2,4-dichlorophenyl) -5-trifluoromethylimidazole-4-carboxamide; Yield: 52.2%; Shape: white solid; Melting point: 129-130 ° C; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 0.70 to 1.05 (m, 6H), 1.05 to 1.31 (m, 3H), 1.31 to 1.75 (m, 5H), 1.75 to 2.40 (m , 2H), 3.00 to 3.25 (m, 1H), 3.45 to 3.75 (m, 1H), 7.31 to 7.50 (m, 2H), 7.53 (s, 1H), 7.58 to 7.65 (m, 1H).

Example-132
Compound name: Nt-butyl-1- (2,5-dichlorophenyl) -5-trifluoromethylimidazole-4-carboxamide; Yield: 66.6%; Shape: pale yellow solid; Melting point: 129-133 ° C .; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 1.49 (s, 9H), 7.16 (br s, 1H), 7.38-7.43 (m, 2H), 7.48-7.52 (m, 2H).

Example-133
Compound name: Nt-butyl-1- (3,5-dichlorophenyl) -5-trifluoromethylimidazole-4-carboxamide; Yield: 59.9%; Shape: pale yellow solid; Melting point: 121-123 ° C .; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 1.48 (s, 9H), 7.09 (br s, 1H), 7.20-7.30 (m, 2H), 7.50 (s, 1H), 7.56 (t, J = 1.8Hz, 1H).

Example-134
Compound name: N- (3-cyano-3-pentyl) -1- (3,5-dichlorophenyl) -5-trifluoromethylimidazole-4-carboxamide; yield: 63.2%; shape: pale yellow solid; melting point: 145-147 ° C .; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 1.12 (t, J = 7.4 Hz, 6H), 2.00-2.30 (m, 4H), 7.29 (d, J = 1.6 Hz, 2H), 7.32 (br s, 1H), 7.55 (s, 1H), 7.58 (t, J = 1.6Hz, 1H).

Example-135
Compound name: Nt-butyl-N-ethyl-1- (3,5-dichlorophenyl) -5-trifluoromethylimidazole-4-carboxamide; yield: 40.8%; shape: white solid: ¹ H-NMR ( CDCl ₃ , TMS, ppm): δ 1.15 (t, J = 7.1Hz, 3H), 1.56 (s, 9H), 3.43 (q, J = 7.1Hz, 2H), 7.34 (d, J = 1.7Hz, 2H), 7.55 (dd, J = 1.7 and 1.7Hz, 1H), 7.60 (s, 1H).

Example-136
Compound name: N, N-diisopropyl-1- (3,5-dichlorophenyl) -5-trifluoromethylimidazole-4-carboxamide; yield: 49.8%; shape: white solid: ¹ H-NMR (CDCl ₃ , TMS , ppm): δ1.20 (d, J = 6.7Hz, 6H), 1.53 (d, J = 6.8Hz, 6H), 3.54 (sept, J = 6.8Hz, 1H), 3.84 (sept, J = 6.7Hz , 1H), 7.35 (d, J = 1.7Hz, 2H), 7.56 (dd, J = 1.7 and 1.7Hz, 2H), 7.62 (s, 1H).

Example-137
Compound name: N- (2,2-dimethyl-3-butyl) -1- (2,6-dichlorophenyl) -5-trifluoromethylimidazole-4-carboxamide; yield: 49.0%; shape: white solid; melting point : 114 to 116 ° C .; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ1.00 (s, 9H), 1.20 (d, J = 6.8 Hz, 3H), 4.00 to 4.15 (m, 1H), 7.10 ~ 7.30 (m, 1H), 7.41 (s, 1H), 7.40 ~ 7.55 (m, 3H).

Example-138
Compound name: N- (3-cyano-3-pentyl) -1- (2,6-dichlorophenyl) -5-trifluoromethylimidazole-4-carboxamide; Yield: 27.5%; Shape: white solid; Melting point: 121 ~ 122 ° C; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 1.14 (t, J = 7.4 Hz, 6H), 2.05 to 2.30 (m, 4H), 7.37 (br s, 1H), 7.42 (s, 1H), 7.43-7.56 (m, 3H).

Example-139
Compound name: N- (2-cyano-4-methyl-2-pentyl) -1- (2,6-dichlorophenyl) -5-trifluoromethylimidazole-4-carboxamide; yield: 60.0%; shape: white solid Melting point: 158 to 161 ° C .; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 1.05 to 1.18 (m, 6H), 1.87 (s, 3H), 1.85 to 2.15 (m, 3H), 7.41 ( s, 1H), 7.40-7.58 (m, 4H).

Example-140
Compound name: N- (2-fluorocyclopropyl) -1- (2,6-dichlorophenyl) -5-trifluoromethylimidazole-4-carboxamide; Yield: 97.0%; Shape: white solid; Melting point: 147-149 ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 1.00 to 1.20 (m, 2H), 3.00 to 3.15 (m, 1H), 4.55 to 4.95 (m, 1H), 7.41 (s, 1H) , 7.43-7.58 (m, 4H).

Example-141
Compound name: N, N-diethyl-1- (2,6-dichlorophenyl) -5-trifluoromethylimidazole-4-carboxamide; Yield: 81.3%; Shape: white solid; Melting point: 116 ° C .; ¹ H- NMR (CDCl ₃ , TMS, ppm): δ 1.17 (t, J = 7.1Hz, 3H), 1.26 (t, J = 7.1Hz, 3H), 3.36 (q, J = 7.1Hz, 1H), 3.58 ( q, J = 7.1Hz, 1H), 7.40-7.55 (m, 3H), 7.51 (s, 1H).

Example-142
Compound name: N-ethyl-N-isopropyl-1- (2,6-dichlorophenyl) -5-trifluoromethylimidazole-4-carboxamide; Yield: 59.8%; Shape: white solid; Melting point: 91-92 ° C. ¹ H-NMR (CDCl ₃ , TMS, ppm): δ1.11 and 1.30 (each t, J = 7.2 and 7.0 Hz, total 3H), 1.21 and 1.31 (each d, J = 6.7 and 6.8 Hz, total 6H ), 3.34 (each q, J = 7.2 and 7.0Hz, total 2H), 3.97 and 4.75 (each sept, J = 6.7 and 6.8Hz, total 1H), 7.40-7.60 (m, 4H).

Example-143
Compound name: Nt-butyl-N-ethyl-1- (2,6-dichlorophenyl) -5-trifluoromethylimidazole-4-carboxamide; Yield: 67.7%; Shape: white solid; Melting point: 112-113 ° C; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 1.14 (t, J = 7.1Hz, 3H), 1.57 (s, 9H), 3.46 (q, J = 7.1Hz, 2H), 7.40 ~ 7.55 (m, 4H).

Example-144
Compound name: Nt-butyl-N-isopropyl-1- (2,6-dichlorophenyl) -5-trifluoromethylimidazole-4-carboxamide; yield: 47.4%; shape: white solid; melting point: 96-97 ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 1.45 (d, J = 7.0 Hz, 6H), 1.46 (s, 9H), 3.80 to 4.07 (sept, J = 7.0 Hz, 1H), 7.40-7.55 (m, 4H).

Example-145
Compound name: N, N-dibutyl-1- (2,6-dichlorophenyl) -5-trifluoromethylimidazole-4-carboxamide; yield: 64.9%; shape: orange oil; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ0.84 (t, J = 7.3Hz, 3H), 0.97 (t, J = 7.3Hz, 3H), 1.10-1.30 (m, 2H), 1.33-1.48 (m, 2H), 1.50 ~ 1.75 (m, 4H), 3.25 ~ 3.38 (m, 2H), 3.45 ~ 3.60 (m, 2H), 7.40 ~ 7.55 (m, 4H).

Example-146
Compound name: N, N-diisobutyl-1- (2,6-dichlorophenyl) -5-trifluoromethylimidazole-4-carboxamide; Yield: 83.9%; Shape: white solid; Melting point: 104-105 ° C .; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 0.82 (d, J = 6.6 Hz, 6H), 0.99 (d, J = 6.7 Hz, 6H), 1.75 to 2.00 (m, 1H), 2.05 to 2.25 (m, 1H), 3.26 (d, J = 7.6Hz, 2H), 3.39 (d, J = 7.5Hz, 1H), 7.40-7.55 (m, 3H), 7.51 (s, 1H).

Example-147
Compound name: N, N-Di-s-butyl-1- (2,6-dichlorophenyl) -5-trifluoromethylimidazole-4-carboxamide; Yield: 68.9%; Shape: white solid; Melting point: 126-127 ° C; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 0.85 (dt, J = 3.5 and 7.4 Hz, 3H), 0.96 (dt, J = 1.5 and 7.4 Hz, 3H), 1.21 (dd, J = 2.6 and 6.7Hz, 3H), 1.30 ~ 1.50 (m, 1H), 1.50 (dd, J = 2.1 and 6.7Hz, 3H), 1.60 ~ 1.80 (m, 1H), 1.80 ~ 2.40 (m 2H), 3.00 ~ 3.25 (m, 1H), 3.60 (tq, J = 6.8 and 6.8Hz, 1H), 7.40 ~ 7.55 (m, 4H).

Example-148
Compound name: N- (2-methoxycarbonyl-3-thienyl) -1- (2,6-dichlorophenyl) -5-trifluoromethylimidazole-4-carboxamide; yield: 49.2%; shape: white solid; melting point: 218 to 219 ° C; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 3.96 (s, 3H), 7.40 to 7.60 (m, 5H), 8.34 (d, J = 5.5Hz, 1H), 11.96 (br s, 1H).

Example-149
Compound name: Nt-butyl-N-ethyl-1- (2,6-difluorophenyl) -5-trifluoromethylimidazole-4-carboxamide; Yield: 32.8%; Shape: white solid; Melting point: 153- 155 ° C .; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 1.15 (t, J = 7.1 Hz, 3H), 1.57 (s, 9H), 3.44 (q, J = 7.1 Hz, 2H), 7.05 ~ 7.20 (m, 2H), 7.45 ~ 7.60 (m, 3H), 7.56 (s, 1H).

Example-150
Compound name: Nt-butyl-N-ethyl-1- (2,6-dichloro-4-trifluoromethylphenyl) -5-trifluoromethylimidazole-4-carboxamide; yield: 37.8%; shape: white Solid; melting point: 223-225 ° C .; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 1.14 (t, J = 7.1 Hz, 3H), 1.57 (s, 9H), 3.46 (q, J = 7.1 Hz, 2H), 7.50 (s, 1H), 7.79 (s, 2H).

Example-151
Compound name: N, N-diisopropyl-1- (2,6-dichlorophenyl) -5-difluoromethyl-imidazole-4-carboxamide; Yield: 59.3%; Morphology: white solid; mp: 155-156 ° C.; ¹ H- NMR (CDCl ₃ , TMS, ppm): δ 1.10 to 1.60 (m, 12H), 3.30 to 3.80 (m, 1H), 4.60 to 5.00 (m, 1H), 7.17 (t, J _HF = 53.0Hz, 1H ), 7.35-7.53 (m, 4H).

Example-152
Compound name: N, N-diisopropyl-1- (2,6-dichlorophenyl) -5-pentafluoroethylimidazole-4-carboxamide; yield: 48.0%; shape: white solid; melting point: 128-129 ° C .; ¹ H -NMR (CDCl ₃ , TMS, ppm): δ 1.21 (d, J = 6.7 Hz, 6H), 1.54 (d, J = 6.8 Hz, 1H), 3.53 (sept, J = 6.8 Hz, 1H), 3.81 (sept, J = 6.7Hz, 1H), 7.35-7.55 (m, 4H).

Example-153
Compound name: Nt-butyl-1- (2,6-diethylphenyl) -5-trifluoromethylimidazole-4-carboxamide; Yield: 84.3%; Shape: white solid; Melting point: 158-159 ° C .; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 1.12 (m, 3Hx2), 1.51 (s, 3Hx3), 2.25 (m, 2Hx2), 7.1 to 7.5 (m, 5H).

Example-154
Compound name: Nt-butyl-N-cyclohexyl-1- (2,6-diethylphenyl) -5-trifluoromethylimidazole-4-carboxamide; Yield: 52.9%; Shape: pale yellow oil; ¹ H -NMR (CDCl ₃ , TMS, ppm): δ 1.14 (m, 3Hx2), 1.5 to 2.2 (m, 20H), 2.30 (m, 2Hx2), 3.45 (m, 1H), 7.2 to 7.5 (m, 4H ).

Example-155
Compound name: N- (2-s-butylphenyl) -1- (2-ethyl-6-methylphenyl) -5-trifluoromethylimidazole-4-carboxamide; yield: 65.1%; shape: white solid; melting point : 118-120 ° C; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 0.98 (m, 3H), 1.18 (m, 3H), 1.33 (d, J = 7.5 Hz, 3H), 1.75 (m , 2H), 2.05 (s, 3H), 2.35 (m, 2H), 3.0 (m, 1H), 7.1-7.5 (m, 7H), 8.20 (m, 1H), 9.35 (br s, NH).

Example-156
Compound name: N- (2-t-butylphenyl) -1- (2,6-dichlorophenyl) -5-trifluoromethylimidazole-4-carboxamide; Yield: 83.0%; Shape: white solid; Melting point: 185- 187 ° C; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ1.54 (s, 3Hx3), 7.0 to 7.6 (m, 7H), 8.21 (d, J = 8.3 Hz, 1H), 9.54 (br s , NH).

Example-157
Compound name: N- (2-iodophenyl) -1- (2,6-dichlorophenyl) -5-trifluoromethylimidazole-4-carboxamide; Yield: 82.4%; Shape: pale yellow solid; Melting point: 165-168 ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 6.87 (m, 1H), 7.3 to 7.6 (m, 5H), 7.83 (m, 1H), 8.54 (m, 1H), 9.70 (br s, NH).

Example-158
Compound name: N- (2-phenoxyphenyl) -1- (2,6-dichlorophenyl) -5-trifluoromethylimidazole-4-carboxamide; Yield: 62.6%; Shape: white solid; Melting point: 199-201 ° C ¹ H-NMR (CDCl ₃ , TMS, ppm): δ6.8 to 7.6 (m, 12H), 8.69 (m, 1H), 9.90 (br s, NH).

Example-159
Compound name: N- (2-s-butylphenyl) -1- (2,6-dichlorophenyl) -5-trifluoromethylimidazole-4-carboxamide; Yield: 65.5%; Shape: white solid; Melting point: 152- ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 0.94 (t, J = 7.0 Hz, 3H), 1.33 (d, J = 6.8 Hz, 3H), 1.70 (m, 2H), 2.90 (m, 1H), 7.0-7.3 (m, 3H), 7.4-7.6 (m, 4H), 8.20 (m, 1H), 9.35 (br s, NH).

Example-160
Compound name: N-t-butyl-1- (2-cyanophenyl) -5-trifluoromethyl-imidazole-4-carboxamide; Yield: 81.0%; Morphology: pale yellow solid; mp: 154 to 156 ° C.; ¹ H -NMR (CDCl ₃ , TMS, ppm): δ 1.50 (s, 9H), 7.14 (br s, NH), 7.49 (d, J = 7.2Hz, 1H), 7.57 (s, 1H), 7.70-7.89 (m, 3H).

Example-161
Compound name: Nt-butyl-N-ethyl-1- (2-cyanophenyl) -5-trifluoromethylimidazole-4-carboxamide; Yield: 80.0%; Shape: pale yellow solid; Melting point: 149-155 ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 1.16 (t, J = 7.1Hz, 3H), 1.57 (s, 9H), 3.46 (q, J = 7.1Hz, 2H), 7.59 ( d, J = 7.8Hz, 1H), 7.66 (s, 1H), 7.72 (d, J = 7.5Hz, 1H), 7.83 (dd, J = 7.5, 7.8Hz, 2H).

Example-162
Compound name: Nt-butyl-N-ethyl-1- (2-trifluoromethylphenyl) -5-trifluoromethylimidazole-4-carboxamide; Yield: 81.2%; Shape: pale yellow solid; Melting point: 138 ˜141 ° C .; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ1.12 (t, J = 7.1 Hz, 3H), 1.57 (s, 9H), 3.30 to 3.59 (m, 2H), 7.51 to 7.58 (m, 2H), 7.70-7.77 (m, 2H), 7.84-7.88 (m, 2H).

Example-163
Compound name: Nt-butyl-N-ethyl-1- (2,3-dichlorophenyl) -5-trifluoromethylimidazole-4-carboxamide; yield: 87.7%; shape: white solid; melting point: 184-188 ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 1.15 (t, J = 7.1 Hz, 3H), 1.57 (s, 9H), 3.42 to 3.51 (m, 2H), 7.39 (m, 2H) ), 7.55 (s, 1H), 7.67 (m, 1H).

Example-164
Compound name: Nt-butyl-N-ethyl-1- (2,5-dichlorophenyl) -5-trifluoromethylimidazole-4-carboxamide; Yield: 55.7%; Shape: white solid; Melting point: 174-177 ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 1.15 (t, J = 7.2 Hz, 3H), 1.56 (s, 9H), 3.45 (m, 2H), 7.42 to 7.58 (m, 4H) ).

Example-165
Compound name: N- [2- (1,3-dimethylbutyl) -3-thienyl] -1- (2,6-dichlorophenyl) -5-trifluoromethylimidazole-4-carboxamide; Yield: 84.3%; Form : Yellow solid; Melting point: 175 to 178 ° C; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 0.91 (d, J = 6.3 Hz, 3H), 0.94 (d, J = 6.3 Hz, 3H), 1.34 (d, J = 7.0Hz, 3H), 1.51-1.60 (m, 3H), 3.21 (m, 3H), 7.12 (d, J = 5.5Hz, 1H), 7.46-7.54 (m, 4H), 7.73 (d, J = 5.3Hz, 1H), 9.00 (br s, NH).

Example-166
Compound name: Nt-butyl-1- (2-chloro-6-trifluoromethylphenyl) -5-trifluoromethylimidazole-4-carboxamide; yield: 85.8%; shape: white solid; melting point: 168- 171 ° C; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 1.50 (s, 9H), 7.19 (br s, NH), 7.38 (s, 1H), 7.65 (dd, J = 7.8, 7.9Hz , 1H), 7.81 (m, 2H).

Example-167
Compound name: Nt-butyl-N-ethyl-1- (2-chloro-6-trifluoromethylphenyl) -5-trifluoromethylimidazole-4-carboxamide; yield: 85.2%; shape: white solid; Melting point: 85-89 ° C .; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ1.13 (t, J = 7.6 Hz, 3H), 1.57 (s, 9H), 3.32 to 3.58 (m, 2H), 7.51 (s, 1H), 7.62-7.88 (m, 3H).

Example-168
Compound name: Nt-butyl-N-cyclohexyl-1- (2,6-dichlorophenyl) -5-trifluoromethylimidazole-4-carboxamide; yield: 57.2%; shape: white solid; melting point: 108-111 ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 0.90 to 1.30 (m, 4H), 1.49 (s, 9H), 1.79 (m, 4H), 2.10 (m, 2H), 3.42 (m , 1H), 7.45-7.54 (m, 4H).

Example-169
Compound name: N-cyclopropyl-1- (2,6-dichlorophenyl) -5-trifluoromethylimidazole-4-carboxamide; Yield: 45.3%; Shape: white solid; Melting point: 110-115 ° C .; ¹ H- NMR (CDCl ₃ , TMS, ppm): δ 0.68 (m, 2H), 0.86 (m, 2H), 2.91 (m, 1H), 7.39 to 7.53 (m, 5H).

Example-170
Compound name: N-cyclohexyl-N-cyclopropyl-1- (2,6-dichlorophenyl) -5-trifluoromethylimidazole-4-carboxamide; yield: 41.1%; shape: white solid; melting point: 164-167 ° C. ¹ H-NMR (CDCl ₃ , TMS, ppm): δ0.50 to 0.75 (m, 4H), 1.05 to 1.52 (m, 2H), 1.60 to 2.02 (m, 8H), 2.67 (m, 1H), 4.22 (m, 1H), 7.39-7.62 (m, 4H).

Example-171
Compound name: N-cyclopropyl-N-isopropyl-1- (2,6-dichlorophenyl) -5-trifluoromethylimidazole-4-carboxamide; Yield: 33.1%; Shape: pale yellow oil; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 1.20 to 1.30 (m, 6H), 1.55 to 1.59 (m, 2H), 1.68 to 2.02 (m, 2H), 3.90 to 4.30 (m, 2H), 7.32 to 7.62 (m, 4H).

Example-172
Compound name: N- [1-Cyano-1-methyl-2- (4-fluorophenoxy) ethyl] -1- (2,6-dichlorophenyl) -5-trifluoromethylimidazole-4-carboxamide; Yield: 47.5 %; Shape: pale yellow solid; Melting point: 163-165 ° C .; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 1.99 (s, 3H), 4.34-4.52 (m, 2H), 6.89-7.08 ( m, 4H), 7.42 (s, 1H), 7.48-7.60 (m, 3H), 7.72 (br s, NH).

Example-173
Compound name: N- (1,1-dimethyl-2-methylthioethyl) -1- (2,6-dichlorophenyl) -5-trifluoromethylimidazole-4-carboxamide; yield: 67.4%; shape: pale yellow solid Melting point: 148 to 150 ° C .; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ1.56 (s, 6H), 2.19 (s, 3H), 3.08 (s, 2H), 7.40 (s, 1H) , 7.41-7.58 (m, 4H).

Example-174
Compound name: Nt-butyl-1- (2,6-dichlorophenyl) -5-trifluoromethylimidazole-4-carboxylthioamide; yield: 59.8%; shape: yellow solid; melting point: 108-112 ° C .; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 1.68 (s, 9H), 7.38 (s, 1H), 7.40-7.60 (m, 3H), 8.61 (br s, NH).

Example-175
Compound name: N- (4-fluorophenyl) -N- (2,2,2-trifluoro-1-methylethyl) -1- (2,6-dichlorophenyl) -5-trifluoromethylimidazole-4-carboxamide Yield: 35.0%; shape: yellow solid; melting point: 155-160 ° C .; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 1.34 (d, J = 7.5 Hz, 3H), 5.74 (m, 1H), 3.92 to 6.98 (m, 2H), 7.00 to 7.30 (m, 3H), 7.30 to 7.60 (m, 3H).

１-(２,６-ジクロロフェニル)-５-トリフルオロメチルイミダゾール-４-カルボン酸(1.5g, 4.2mmol)のトルエン(20mL)溶液に、塩化チオニル(8.4mL)を加え、この溶液を１２０℃で２時間加熱還流した後、オイルバスの温度を１６０℃まで昇温し、ディーン・スタークを用いてトルエン及び過剰の塩化チオニルを除去した。次いで反応混合物を室温まで冷却した後、アセトン(10mL)を加え、さらに氷冷下で酢酸アンモニウム(0.3g, 4.4mmol)を加え、徐々に室温まで昇温させ、そのままの温度で１２時間撹拌した。反応終了後、アセトンを減圧下で留去し、得られた混合物に弱酸性になるまで２Ｎ-塩酸を加え、酢酸エチル(10mL×3)で抽出した。有機層を合わせ無水硫酸マグネシウムで乾燥し、乾燥剤をろ過後、溶媒を減圧下で留去した。得られた残渣をシリカゲルカラムクロマトグラフィー（酢酸エチル：ヘキサン＝1：1）で精製することにより、１-(２,６-ジクロロフェニル)-５-トリフルオロメチルイミダゾール-４-カルボキサミドの白色固体(1.0g,収率：70.4％)を得た。融点：249〜250℃；¹H-NMR(CDCl₃, TMS, ppm)：δ5.71(br s, 1H), 7.17(br s, 1H), 7.35〜7.60(m, 4H). Example-176

To a solution of 1- (2,6-dichlorophenyl) -5-trifluoromethylimidazole-4-carboxylic acid (1.5 g, 4.2 mmol) in toluene (20 mL) was added thionyl chloride (8.4 mL). Then, the temperature of the oil bath was raised to 160 ° C., and toluene and excess thionyl chloride were removed using Dean Stark. Next, after the reaction mixture was cooled to room temperature, acetone (10 mL) was added, and further ammonium acetate (0.3 g, 4.4 mmol) was added under ice-cooling. The mixture was gradually warmed to room temperature and stirred at that temperature for 12 hours. . After completion of the reaction, acetone was distilled off under reduced pressure, 2N-hydrochloric acid was added to the resulting mixture until it became weakly acidic, and the mixture was extracted with ethyl acetate (10 mL × 3). The organic layers were combined and dried over anhydrous magnesium sulfate, the desiccant was filtered off, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate: hexane = 1: 1) to give 1- (2,6-dichlorophenyl) -5-trifluoromethylimidazole-4-carboxamide as a white solid (1.0 g, yield: 70.4%). Melting point: 249-250 ° C .; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ5.71 (br s, 1H), 7.17 (br s, 1H), 7.35-7.60 (m, 4H).

  Examples 177 to 181 were obtained in the same manner as Example 176 to obtain imidazole-4-carboxamide derivatives.

Example-177
Compound name: 1- (4-t-butylphenyl) -5-trifluoromethylimidazole-4-carboxamide; Yield: 25.0%; Shape: white solid; Melting point: 249-251 ° C .; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 1.37 (s, 9H), 5.50 (br s, 1H), 7.10 (br s, 1H), 7.23 to 7.33 (m, 2H), 7.44 to 7.58 (m, 2H), 7.55 (s, 1H).

Example-178
Compound name: 1- (2,4-dichlorophenyl) -5-trifluoromethylimidazole-4-carboxamide; Yield: 13.5%; Shape: white solid; Melting point: 199-200 ° C .; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ5.52 (br s, 1H), 7.11 (br s, 1H), 7.35 (d, J = 5.0Hz, 1H), 7.44 (dd, J = 2.5 and 5.0Hz, 1H), 7.47 (s, 1H), 7.61 (d, J = 2.5Hz, 1H).

Example-179
Compound name: 1- (2,6-dichloro-4-trifluoromethylphenyl) -5-trifluoromethylimidazole-4-carboxamide; yield: 95.3%; shape: white solid; melting point: 237-239 ° C .; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 5.68 (br s, 1H), 7.15 (br s, 1H), 7.79 (s, 2H), 7.82 (s, 1H).

Example-180
Compound name: 1- (2,6-dichloro-4-trifluoromethoxyphenyl) -5-trifluoromethylimidazole-4-carboxamide; yield: 93.7%; shape: white solid; melting point: 249-250 ° C .; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 5.70 (br s, 1H), 7.15 (br s, 1H), 7.41 (s, 2H), 7.43 (s, 1H).

Example-181
Compound name: 1- (4-Chloro-2-fluoro-5-propargyloxyphenyl) -5-trifluoromethylimidazole-4-carboxamide; Yield: 27.6%; Shape: pale yellow solid; Melting point: 179-180 ° C. ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 2.59 (t, J = 2.5 Hz, 1H), 4.80 (d, J = 2.5 Hz, 2H), 5.60 (br s, 1H), 7.00 to 7.20 (m, 1H), 7.12 (d, J _HF = 5.0Hz, 1H), 7.39 (d, J _HF = 10.0Hz, 1H), 7.54 (s, 1H).

１-(２,６-ジクロロフェニル)-５-トリフルオロメチルイミダゾール-４-カルボキサミド(0.12g, 0.31mmol)及び炭酸カリウム(0.57g, 4.12mmol)のアセトニトリル(2mL)溶液に、塩化ホスホリル(0.38mL)を加え、この溶液を６０℃で５時間加熱撹拌した。反応終了後、反応混合物を氷水にあけ、酢酸エチル(10mL×3)で抽出した。有機層を合わせ無水硫酸マグネシウムで乾燥し、乾燥剤をろ過後、溶媒を減圧下で留去した。得られた残渣をシリカゲルカラムクロマトグラフィー（酢酸エチル：ヘキサン＝1：2）で精製することにより、４-シアノ-１-(２,６-ジクロロフェニル)-５-トリフルオロメチルイミダゾールの淡黄色固体(0.08g, 収率：88.9％)を得た。融点：160〜162℃；¹H-NMR(CDCl₃, TMS, ppm)：δ7.54(s, 1H), 7.52〜7.63(m, 3H). Example-182

To a solution of 1- (2,6-dichlorophenyl) -5-trifluoromethylimidazole-4-carboxamide (0.12 g, 0.31 mmol) and potassium carbonate (0.57 g, 4.12 mmol) in acetonitrile (2 mL) was added phosphoryl chloride (0.38 mL). ) Was added and the solution was stirred with heating at 60 ° C. for 5 hours. After completion of the reaction, the reaction mixture was poured into ice water and extracted with ethyl acetate (10 mL × 3). The organic layers were combined and dried over anhydrous magnesium sulfate, the desiccant was filtered off, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate: hexane = 1: 2) to give a light yellow solid of 4-cyano-1- (2,6-dichlorophenyl) -5-trifluoromethylimidazole ( 0.08 g, yield: 88.9%). Melting point: 160-162 ° C .; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 7.54 (s, 1H), 7.52-7.63 (m, 3H).

  Examples 183 to 188 obtained 4-cyanoimidazole derivatives in the same manner as Example-182.

Example-183
Compound name: 1- (4-t-butylphenyl) -4-cyano-5-trifluoromethylimidazole; Yield: 35.5%; Shape: white solid; Melting point: 78-80 ° C .; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 1.38 (s, 9H), 7.28 (dd, J = 2.2 and 6.6Hz, 2H), 7.55 (dd, J = 2.2 and 6.6Hz, 2H), 7.69 (s, 1H).

Example-184
Compound name: 4-cyano-1- (2,4-dichlorophenyl) -5-trifluoromethylimidazole; yield: 91.9%; shape: white solid; melting point: 108-110 ° C .; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 7.39 (d, J = 7.5Hz, 1H), 7.47 (dd, J = 2.5 and 7.5Hz, 1H), 7.64 (s, 1H), 7.64 (d, J = 2.5Hz, 1H ).

Example-185
Compound name: 4-cyano-1- (2,6-dichloro-4-trifluoromethylphenyl) -5-trifluoromethylimidazole; yield: 50.0%; shape: white solid; melting point: 138-140 ° C .; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 7.59 and 7.60 (each s, total 1H), 7.83 (s, 2H).

Example-186
Compound Name: 4-Cyano-1- (2,6-dichloro-4-trifluoromethoxyphenyl) -5-trifluoromethyl-imidazole; Yield: 57.4%; Morphology: white solid; mp: 153-156 ° C.; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 7.44 (s, 2H), 7.60 (s, 1H).

Example-187
Compound name: 1- (4-Chloro-5-cyclopentyloxy-2-fluorophenyl) -4-cyano-5-trifluoromethylimidazole; Yield: 26.2%; Shape: white solid; Melting point: 93-94 ° C .; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ1.54 to 1.80 (m, 2H), 1.80 to 2.05 (m, 6H), 4.65 to 4.80 (m, 1H), 6.92 (d, J _HF = 6.5 Hz, 1H), 7.38 (d, J _HF = 9.0Hz, 1H), 7.71 and 7.71 (each s, total 1H).

Example-188
Compound name: 1- (4-chloro-2-fluoro-5-propargyloxyphenyl) -4-cyano-5-trifluoromethylimidazole; yield: 52.6%; shape: white solid; melting point: 122-125 ° C .; ¹ H-NMR (CDCl ₃ , TMS, ppm): δ 2.59 (t, J = 2.4Hz, 1H), 4.80 (d, J = 2.4Hz, 2H), 7.14 (d, J _HF = 6.4Hz, 1H ), 7.43 (d, J _HF = 8.7Hz, 1H), 7.70 and 7.70 (each s, total 1H).

  Examples of imidazole derivatives according to the present invention synthesized by the methods exemplified in the above examples are summarized in Tables 1 and 2.

─────────────────────────────────
化合物 実施例
Ｎｏ. Ｎｏ. Ｘｎ Ｒ^１ Ｒ^３ Ｒ^４
─────────────────────────────────
1 H CF₃ Me H
2 H CF₃ Et H
3 H CF₃ i-Pr H
4 H CF₃ t-Bu H
5 2-Me CHF₂ Me H
6 2-Me CHF₂ Et H
7 2-Me CHF₂ i-Pr H
8 2-Me CHF₂ i-Pr 4-F-C₆H₄
───────────────────────────────── Table 1 5-Trifluoromethylimidazole-4-carboxamide derivatives

─────────────────────────────────
Compound Example No. No. Xn R ¹ R ³ R ⁴
─────────────────────────────────
1 H CF ₃ Me H
2 H CF ₃ Et H
3 H CF ₃ i-Pr H
4 H CF ₃ t-Bu H
5 2-Me CHF ₂ Me H
6 2-Me CHF ₂ Et H
7 2-Me CHF ₂ i-Pr H
8 2-Me CHF ₂ i-Pr 4-FC ₆ H ₄
─────────────────────────────────

Continuation of Table-1 ─────────────────────────────────
Compound Example No. No. Xn R ¹ R ³ R ⁴
─────────────────────────────────
9 2-Me CHF ₂ i-Pr 2,4-F ₂ -C ₆ H ₃
10 2-Me CHF ₂ Bu H
11 2-Me CHF ₂ s-Bu H
12 2-Me CHF ₂ i-Bu H
13 2-Me CHF ₂ t-Bu H
14 2-Me CHF ₂ Neopentyl H
15 2-Me CHF ₂ t-Amyl H
16 2-Me CHF ₂ Propargyl H
17 2-Me CHF ₂ EtO H
18 2-Me CHF ₂ t-BuO H
19 19 2-Me CF ₃ Me H
20 2-Me CF ₃ Me Me
21 2-Me CF ₃ Me Et
22 2-Me CF ₃ Et H
23 2-Me CF ₃ Et Et
24 2-Me CF ₃ Et Cyclohexyl
25 2-Me CF ₃ Et C ₆ H ₅
26 2-Me CF ₃ Et 4-FC ₆ H ₄
27 2-Me CF ₃ Et 2,4-F ₂ -C ₆ H ₃
28 108 2-Me CF ₃ Et t-Bu
29 2-Me CF ₃ Pr H
30 2-Me CF ₃ i-Pr H
31 2-Me CF ₃ i-Pr i-Pr
32 2-Me CF ₃ i-Pr 4-FC ₆ H ₄
33 2-Me CF ₃ i-Pr 2,4-F ₂ -C ₆ H ₃
34 2-Me CF ₃ Bu H
35 2-Me CF ₃ s-Bu H
36 2-Me CF ₃ i-Bu H
37 36 2-Me CF ₃ t-Bu H
38 2-Me CF ₃ Hexyl H
39 2-Me CF ₃ ClCH ₂ CH ₂ H
40 2-Me CF ₃ BrCH ₂ CH ₂ H
41 2-Me CF ₃ Tetrahydrofurfuryl H
42 2-Me CF ₃ Allyl H
43 3 2-Me CF ₃ Propargyl H
44 2-Me CF ₃ Cyclopropyl H
45 2-Me CF ₃ Cyclohexyl H
46 2-Me CF ₃ C ₆ H ₅ H
47 2-Me CF ₃ 4-Cl-C ₆ H ₄ H
48 2-Me CF ₃ 4-FC ₆ H ₄ H
49 2-Me CF ₃ 2,4-Cl ₂ -C ₆ H ₃ H
50 2-Me CF ₃ 2,4-F ₂ -C ₆ H ₃ H
─────────────────────────────────

Continuation of Table-1 ─────────────────────────────────
Compound Example No. No. Xn R ¹ R ³ R ⁴
─────────────────────────────────
51 2-Me CF ₃ 4-t-Bu-C ₆ H ₄ CH ₂ H
52 2-Me CHF ₂ EtO H
53 2-Me CHF ₂ t-BuO H
54 38 2-Me CF ₃ -CH ₂ CH ₂ CH ₂ CH _2-
55 3-Me CF ₃ Me H
56 4-Me CF ₃ Me H
57 112 2-Et-6-Me CF ₃ t-Bu H
58 113 2-Et-6-Me CF ₃ t-Bu Et
59 114 2,6-Et ₂ CF ₃ t-Bu Et
60 2-t-Bu CF ₃ Me H
61 109 2-t-Bu CF ₃ t-Bu H
62 110 2-t-Bu CF ₃ t-Bu Et
62 111 2-t-Bu CF ₃ t-Bu i-Pr
64 3-t-Bu CF ₃ Me H
65 177 4-t-Bu CF ₃ HH
66 20 4-t-Bu CF ₃ Me H
67 2-CF ₃ CF ₃ Me H
68 117 2-CF ₃ CF ₃ t-Bu H
69 162 2-CF ₃ CF ₃ t-Bu Et
70 118 2-CF ₃ CF ₃ t-Bu i-Pr
71 3-CF ₃ CF ₃ Me H
72 39 3-CF ₃ CF ₃ 2,4-F ₂ -C ₆ H ₃ H
73 4-CF ₃ CF ₃ Me H
74 2-CN CF ₃ Me H
75 3-CN CF ₃ Me H
76 4-CN CF ₃ Me H
77 2-MeO CF ₃ Me H
78 3-MeO CF ₃ Me H
79 4-MeO CF ₃ Me H
80 115 2-C ₆ H ₅ CF ₃ t-Bu H
81 116 2-C ₆ H ₅ CF ₃ t-Bu Et
82 2-Br CF ₃ Me H
83 2-Br CF ₃ Me Me
84 2-Br CF ₃ Me Et
85 2-Br CF ₃ Et H
86 2-Br CF ₃ Et Et
87 2-Br CF ₃ Et Cyclohexyl
88 2-Br CF ₃ Et C ₆ H ₅
89 2-Br CF ₃ Et 4-FC ₆ H ₄
90 2-Br CF ₃ Et 2,4-F ₂ -C ₆ H ₃
91 2-Br CF ₃ Pr H
92 2-Br CF ₃ i-Pr H
93 2-Br CF ₃ i-Pr i-Pr
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Continuation of Table-1 ─────────────────────────────────
Compound Example No. No. Xn R ¹ R ³ R ⁴
─────────────────────────────────
94 2-Br CF ₃ i-Pr 4-FC ₆ H ₄
95 2-Br CF ₃ i-Pr 2,4-F ₂ -C ₆ H ₃
96 2-Br CF ₃ Bu H
97 2-Br CF ₃ s-Bu H
98 2-Br CF ₃ i-Bu H
99 119 2-Br CF ₃ t-Bu H
100 120 2-Br CF ₃ t-Bu Et
101 2-Br CF ₃ Hexyl H
102 2-Br CF ₃ ClCH ₂ CH ₂ H
103 2-Br CF ₃ BrCH ₂ CH ₂ H
104 2-Br CF ₃ Tetrahydrofurfuryl H
105 2-Br CF ₃ Allyl H
106 2-Br CF ₃ Cyclopropyl H
107 2-Br CF ₃ Cyclohexyl H
108 2-Br CF ₃ C ₆ H ₅ H
109 2-Br CF ₃ 4-Cl-C ₆ H ₄ H
110 2-Br CF ₃ 4-FC ₆ H ₄ H
111 2-Br CF ₃ 2,4-Cl ₂ -C ₆ H ₃ H
112 2-Br CF ₃ 2,4-F ₂ -C ₆ H ₃ H
113 2-Br CF ₃ 4-t-Bu-C ₆ H ₄ CH ₂ H
114 3-Br CF ₃ Me H
115 21 4-Br CF ₃ Me H
116 4-Br CF ₃ Me Me
117 4-Br CF ₃ Me Et
118 45 4-Br CF ₃ Et H
119 4-Br CF ₃ Et Et
120 47 4-Br CF ₃ Et Cyclohexyl
121 48 4-Br CF ₃ Et C ₆ H ₅
122 4-Br CF ₃ Et 4-FC ₆ H ₄
123 4-Br CF ₃ Et 2,4-F ₂ -C ₆ H ₃
124 4-Br CF ₃ Pr H
125 46 4-Br CF ₃ i-Pr H
126 4-Br CF ₃ i-Pr i-Pr
127 4-Br CF ₃ i-Pr 4-FC ₆ H ₄
128 4-Br CF ₃ i-Pr 2,4-F ₂ -C ₆ H ₃
129 4-Br CF ₃ Bu H
130 4-Br CF ₃ s-Bu H
131 4-Br CF ₃ i-Bu H
132 4-Br CF ₃ t-Bu H
133 121 4-Br CF ₃ t-Bu Et
134 4-Br CF ₃ Hexyl H
135 4-Br CF ₃ ClCH ₂ CH ₂ H
136 4-Br CF ₃ BrCH ₂ CH ₂ H
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Continuation of Table-1 ─────────────────────────────────
Compound Example No. No. Xn R ¹ R ³ R ⁴
─────────────────────────────────
137 4-Br CF ₃ Tetrahydrofurfuryl H
138 4-Br CF ₃ Allyl H
139 4-Br CF ₃ Cyclopropyl H
140 4-Br CF ₃ Cyclohexyl H
141 4-Br CF ₃ C ₆ H ₅ H
142 4-Br CF ₃ 4-Cl-C ₆ H ₄ H
143 4-Br CF ₃ 4-FC ₆ H ₄ H
144 4-Br CF ₃ 2,4-Cl ₂ -C ₆ H ₃ H
145 4-Br CF ₃ 2,4-F ₂ -C ₆ H ₃ H
146 4-Br CF ₃ 4-t-Bu-C ₆ H ₄ CH ₂ H
147 2-Cl CHF ₂ Me H
148 2-Cl CHF ₂ Et H
149 2-Cl CHF ₂ i-Pr H
150 2-Cl CHF ₂ i-Pr 4-FC ₆ H ₄
151 2-Cl CHF ₂ i-Pr 2,4-F ₂ -C ₆ H ₃
152 2-Cl CHF ₂ Bu H
153 2-Cl CHF ₂ s-Bu H
154 2-Cl CHF ₂ i-Bu H
155 2-Cl CHF ₂ t-Bu H
156 2-Cl CHF ₂ Neopentyl H
157 2-Cl CHF ₂ t-Amyl H
158 2-Cl CHF ₂ Propargyl H
159 2-Cl CHF ₂ EtO H
160 2-Cl CHF ₂ t-BuO H
161 22 2-Cl CF ₃ Me H
162 2-Cl CF ₃ Me Me
163 2-Cl CF ₃ Me Et
164 2-Cl CF ₃ Et H
165 2-Cl CF ₃ Et Et
166 42 2-Cl CF ₃ Et Cyclohexyl
167 43 2-Cl CF ₃ Et C ₆ H ₅
168 2-Cl CF ₃ Et 4-FC ₆ H ₄
169 2-Cl CF ₃ Et 2,4-F ₂ -C ₆ H ₃
170 2-Cl CF ₃ Pr H
171 2-Cl CF ₃ i-Pr H
172 2-Cl CF ₃ i-Pr i-Pr
173 44 2-Cl CF ₃ i-Pr 4-FC ₆ H ₄
174 2-Cl CF ₃ i-Pr 2,4-F ₂ -C ₆ H ₃
175 2-Cl CF ₃ Bu H
176 2-Cl CF ₃ s-Bu H
177 2-Cl CF ₃ i-Bu H
178 40 2-Cl CF ₃ t-Bu H
179 122 2-Cl CF ₃ t-Bu Et
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Continuation of Table-1 ─────────────────────────────────
Compound Example No. No. Xn R ¹ R ³ R ⁴
─────────────────────────────────
180 2-Cl CF ₃ Hexyl H
181 2-Cl CF ₃ ClCH ₂ CH ₂ H
182 2-Cl CF ₃ BrCH ₂ CH ₂ H
183 2-Cl CF ₃ Tetrahydrofurfuryl H
184 2-Cl CF ₃ Allyl H
185 2-Cl CF ₃ Cyclopropyl H
186 2-Cl CF ₃ Cyclohexyl H
187 2-Cl CF ₃ C ₆ H ₅ H
188 2-Cl CF ₃ 2,4-F ₂ -C ₆ H ₃ H
189 2-Cl CF ₃ 4-t-Bu-C ₆ H ₄ CH ₂ H
190 2-Cl CHF ₂ EtO H
191 2-Cl CHF ₂ t-BuO H
192 41 2-Cl CF ₃ -CH ₂ CH ₂ CH ₂ CH _2-
193 3-Cl CF ₃ Me H
194 23 4-Cl CF ₃ Me H
195 4-Cl CF ₃ Me Me
196 4-Cl CF ₃ Me Et
197 4-Cl CF ₃ Et H
198 4-Cl CF ₃ Et Et
199 4-Cl CF ₃ Et Cyclohexyl
200 4-Cl CF ₃ Et C ₆ H ₅
201 4-Cl CF ₃ Et 4-FC ₆ H ₄
202 4-Cl CF ₃ Et 2,4-F ₂ -C ₆ H ₃
203 4-Cl CF ₃ Pr H
204 50 4-Cl CF ₃ i-Pr H
205 4-Cl CF ₃ i-Pr i-Pr
206 4-Cl CF ₃ i-Pr 4-FC ₆ H ₄
207 4-Cl CF ₃ i-Pr 2,4-F ₂ -C ₆ H ₃
208 4-Cl CF ₃ Bu H
209 4-Cl CF ₃ s-Bu H
210 4-Cl CF ₃ i-Bu H
211 4-Cl CF ₃ t-Bu H
212 51 4-Cl CF ₃ Neopentyl H
213 4-Cl CF ₃ Hexyl H
214 4-Cl CF ₃ ClCH ₂ CH ₂ H
215 4-Cl CF ₃ BrCH ₂ CH ₂ H
216 4-Cl CF ₃ Tetrahydrofurfuryl H
217 4-Cl CF ₃ Allyl H
218 49 4-Cl CF ₃ Cyclopropyl H
219 4-Cl CF ₃ Cyclohexyl H
220 4-Cl CF ₃ C ₆ H ₅ H
221 4-Cl CF ₃ 4-Cl-C ₆ H ₄ H
222 4-Cl CF ₃ 4-FC ₆ H ₄ H
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Continuation of Table-1 ─────────────────────────────────
Compound Example No. No. Xn R ¹ R ³ R ⁴
─────────────────────────────────
223 4-Cl CF ₃ 2,4-Cl ₂ -C ₆ H ₃ H
224 52 4-Cl CF ₃ 2,4-F ₂ -C ₆ H ₃ H
225 4-Cl CF ₃ 4-t-Bu-C ₆ H ₄ CH ₂ H
226 2-F CF ₃ Me H
227 3-F CF ₃ Me H
228 4-F CF ₃ Me H
229 160 2-CN CF ₃ t-Bu H
230 161 2-CN CF ₃ t-Bu Et
231 2-NO ₂ CF ₃ Me H
232 3-NO ₂ CF ₃ Me H
233 24 4-NO ₂ CF ₃ Me H
234 2,6-Me ₂ CHF ₂ Me H
235 2,6-Me ₂ CHF ₂ Et H
236 2,6-Me ₂ CHF ₂ i-Pr H
237 2,6-Me ₂ CHF ₂ i-Pr 4-FC ₆ H ₄
238 2,6-Me ₂ CHF ₂ i-Pr 2,4-F ₂ -C ₆ H ₃
239 2,6-Me ₂ CHF ₂ Bu H
240 2,6-Me ₂ CHF ₂ s-Bu H
241 2,6-Me ₂ CHF ₂ i-Bu H
242 2,6-Me ₂ CHF ₂ t-Bu H
243 2,6-Me ₂ CHF ₂ Neopentyl H
244 2,6-Me ₂ CHF ₂ t-Amyl H
245 2,6-Me ₂ CHF ₂ Propargyl H
246 2,6-Me ₂ CHF ₂ EtO H
247 2,6-Me ₂ CHF ₂ t-BuO H
248 25 2,6-Me ₂ CF ₃ Me H
249 2,6-Me ₂ CF ₃ Et H
250 55 2,6-Me ₂ CF ₃ Et C ₆ H ₅
251 2,6-Me ₂ CF ₃ Pr H
252 56 2,6-Me ₂ CF ₃ i-Pr 4-FC ₆ H ₄
253 57 2,6-Me ₂ CF ₃ i-Pr 2,4-F ₂ -C ₆ H ₃
254 53 2,6-Me ₂ CF ₃ t-Bu H
255 54 2,6-Me ₂ CF ₃ 4-t-Bu-C ₆ H ₄ H
256 2,6-Me ₂ CHF ₂ EtO H
257 2,6-Me ₂ CHF ₂ t-BuO H
258 153 2,6-Et ₂ CF ₃ t-Bu H
259 154 2,6-Et ₂ CF ₃ t-Bu Cyclohexyl
260 155 2-Et-6-Me CF ₃ s-Bu-C ₆ H ₄ Cyclohexyl
261 123 2,6-Br ₂ CF ₃ t-Bu H
262 124 2,6-Br ₂ CF ₃ t-Bu Et
263 125 2,6-Br ₂ CF ₃ t-Bu i-Pr
264 2,3-Cl ₂ CF ₃ Me H
265 126 2,3-Cl ₂ CF ₃ t-Bu H
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Continuation of Table-1 ─────────────────────────────────
Compound Example No. No. Xn R ¹ R ³ R ⁴
─────────────────────────────────
266 163 2,3-Cl ₂ CF ₃ t-Bu Et
267 2,4-Cl ₂ CHF ₂ Me H
268 2,4-Cl ₂ CHF ₂ Et H
269 2,4-Cl ₂ CHF ₂ i-Pr H
270 2,4-Cl ₂ CHF ₂ i-Pr 4-FC ₆ H ₄
271 2,4-Cl ₂ CHF ₂ i-Pr 2,4-F ₂ -C ₆ H ₃
272 2,4-Cl ₂ CHF ₂ Bu H
273 2,4-Cl ₂ CHF ₂ s-Bu H
274 2,4-Cl ₂ CHF ₂ i-Bu H
275 2,4-Cl ₂ CHF ₂ t-Bu H
276 129 2,4-Cl ₂ CF ₃ t-Bu Et
277 2,4-Cl ₂ CHF ₂ Neopentyl H
278 2,4-Cl ₂ CHF ₂ t-Amyl H
279 2,4-Cl ₂ CHF ₂ Propargyl H
280 2,4-Cl ₂ CHF ₂ EtO H
281 2,4-Cl ₂ CHF ₂ t-BuO H
282 178 2,4-Cl ₂ CF ₃ HH
283 26 2,4-Cl ₂ CF ₃ Me H
284 58 2,4-Cl ₂ CF ₃ Me Me
285 2,4-Cl ₂ CF ₃ Me Et
286 59 2,4-Cl ₂ CF ₃ Et H
287 2,4-Cl ₂ CF ₃ Et Et
288 2,4-Cl ₂ CF ₃ Et Cyclohexyl
289 2,4-Cl ₂ CF ₃ Et C ₆ H ₅
290 2,4-Cl ₂ CF ₃ Et 4-FC ₆ H ₄
291 2,4-Cl ₂ CF ₃ Et 2,4-F ₂ -C ₆ H ₃
292 60 2,4-Cl ₂ CF ₃ Pr H
293 61 2,4-Cl ₂ CF ₃ i-Pr H
294 128 2,4-Cl ₂ CF ₃ i-Pr i-Pr
295 2,4-Cl ₂ CF ₃ i-Pr 4-FC ₆ H ₄
296 2,4-Cl ₂ CF ₃ i-Pr 2,4-F ₂ -C ₆ H ₃
297 2,4-Cl ₂ CF ₃ Bu H
298 63 2,4-Cl ₂ CF ₃ s-Bu H
299 130 2,4-Cl ₂ CF ₃ s-Bu Pr
300 131 2,4-Cl ₂ CF ₃ s-Bu s-Bu
301 62 2,4-Cl ₂ CF ₃ i-Bu H
302 2,4-Cl ₂ CF ₃ t-Bu H
303 64 2,4-Cl ₂ CF ₃ Hexyl H
304 2,4-Cl ₂ CF ₃ ClCH ₂ CH ₂ H
305 2,4-Cl ₂ CF ₃ BrCH ₂ CH ₂ H
306 65 2,4-Cl ₂ CF ₃ Tetrahydrofurfuryl H
307 2,4-Cl ₂ CF ₃ Allyl H
308 67 2,4-Cl ₂ CF ₃ Propargyl H
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Continuation of Table-1 ─────────────────────────────────
Compound Example No. No. Xn R ¹ R ³ R ⁴
─────────────────────────────────
309 66 2,4-Cl ₂ CF ₃ Cyclopropyl H
310 2,4-Cl ₂ CF ₃ Cyclohexyl H
311 2,4-Cl ₂ CF ₃ C ₆ H ₅ H
312 2,4-Cl ₂ CF ₃ 4-Cl-C ₆ H ₄ H
313 69 2,4-Cl ₂ CF ₃ 4-FC ₆ H ₄ H
314 2,4-Cl ₂ CF ₃ 2,4-Cl ₂ -C ₆ H ₃ H
315 2,4-Cl ₂ CF ₃ 2,4-F ₂ -C ₆ H ₃ H
316 68 2,4-Cl ₂ CF ₃ 4-t-Bu-C ₆ H ₄ CH ₂ H
317 127 2,4-Cl ₂ CF ₃ 3-cyano-3-pentyl H
318 2,4-Cl ₂ CHF ₂ EtO H
319 2,4-Cl ₂ CHF ₂ t-BuO H
320 2,5-Cl ₂ CF ₃ Me H
321 132 2,5-Cl ₂ CF ₃ t-Bu H
322 164 2,5-Cl ₂ CF ₃ t-Bu Et
323 33 2,6-Cl ₂ CHF ₂ Me H
324 102 2,6-Cl ₂ CHF ₂ Et H
325 2,6-Cl ₂ CHF ₂ i-Pr H
326 151 2,6-Cl ₂ CHF ₂ i-Pr i-Pr
327 106 2,6-Cl ₂ CHF ₂ i-Pr 4-FC ₆ H ₄
328 107 2,6-Cl ₂ CHF ₂ i-Pr 2,4-F ₂ -C ₆ H ₃
329 2,6-Cl ₂ CHF ₂ Bu H
330 2,6-Cl ₂ CHF ₂ s-Bu H
331 2,6-Cl ₂ CHF ₂ i-Bu H
332 103 2,6-Cl ₂ CHF ₂ t-Bu H
333 2,6-Cl ₂ CHF ₂ Neopentyl H
334 2,6-Cl ₂ CHF ₂ t-Amyl H
335 2,6-Cl ₂ CHF ₂ Propargy H
336 104 2,6-Cl ₂ CHF ₂ EtO H
337 105 2,6-Cl ₂ CHF ₂ t-BuO H
338 176 2,6-Cl ₂ CF ₃ HH
339 18 2,6-Cl ₂ CF ₃ Me H
340 2,6-Cl ₂ CF ₃ Me Me
341 2,6-Cl ₂ CF ₃ Me Et
342 70 2,6-Cl ₂ CF ₃ Et H
343 141 2,6-Cl ₂ CF ₃ Et Et
344 90 2,6-Cl ₂ CF ₃ Et Cyclohexyl
345 142 2,6-Cl ₂ CF ₃ Et i-Pr
346 2,6-Cl ₂ CF ₃ Et C ₆ H ₅
347 2,6-Cl ₂ CF ₃ Et 4-FC ₆ H ₄
348 2,6-Cl ₂ CF ₃ Et 2,4-F ₂ -C ₆ H ₃
349 71 2,6-Cl ₂ CF ₃ Pr H
350 72 2,6-Cl ₂ CF ₃ i-Pr H
351 89 2,6-Cl ₂ CF ₃ i-Pr i-Pr
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Continuation of Table-1 ─────────────────────────────────
Compound Example No. No. Xn R ¹ R ³ R ⁴
─────────────────────────────────
352 91 2,6-Cl ₂ CF ₃ i-Pr 4-FC ₆ H ₄
353 92 2,6-Cl ₂ CF ₃ i-Pr 2,4-F ₂ -C ₆ H ₃
354 2,6-Cl ₂ CF ₃ Bu H
355 145 2,6-Cl ₂ CF ₃ Bu Bu
356 73 2,6-Cl ₂ CF ₃ s-Bu H
357 147 2,6-Cl ₂ CF ₃ s-Bu s-Bu
358 2,6-Cl ₂ CF ₃ i-Bu H
359 146 2,6-Cl ₂ CF ₃ i-Bu i-Bu
360 35 2,6-Cl ₂ CF ₃ t-Bu H
361 143 2,6-Cl ₂ CF ₃ t-Bu Et
362 144 2,6-Cl ₂ CF ₃ t-Bu i-Pr
363 74 2,6-Cl ₂ CF ₃ Neopentyl H
364 75 2,6-Cl ₂ CF ₃ t-Amyl H
365 76 2,6-Cl ₂ CF ₃ Hexyl H
366 2,6-Cl ₂ CF ₃ ClCH ₂ CH ₂ H
367 2,6-Cl ₂ CF ₃ BrCH ₂ CH ₂ H
368 77 2,6-Cl ₂ CF ₃ CF ₃ CH ₂ CH ₂ H
369 2,6-Cl ₂ CF ₃ Tetrahydrofurfuryl H
370 2,6-Cl ₂ CF ₃ Allyl H
371 83 2,6-Cl ₂ CF ₃ Propargyl H
372 2,6-Cl ₂ CF ₃ Cyclopropyl H
373 140 2,6-Cl ₂ CF ₃ 2-F-Cyclopropyl H
374 81 2,6-Cl ₂ CF ₃ Cyclohexyl H
375 82 2,6-Cl ₂ CF ₃ 1-Adamantyl H
376 2,6-Cl ₂ CF ₃ C ₆ H ₅ H
377 2,6-Cl ₂ CF ₃ 4-Cl-C ₆ H ₄ H
378 175 2,6-Cl ₂ CF ₃ 4-FC ₆ H ₄ CF ₃ CH ₂
379 84 2,6-Cl ₂ CF ₃ 2-FC ₆ H ₄ H
380 172 2,6-Cl ₂ CF ₃ 4-FC ₆ H ₄ OCH ₂ C (CH ₃ ) (CN) H
381 138 2,6-Cl ₂ CF ₃ CH ₃ CHC (CH ₃ CH ₂ ) (CN) H
382 139 2,6-Cl ₂ CF ₃ CH ₃ CH (CH ₃ ) CH ₂ C (CH ₃ ) (CN) H
383 2,6-Cl ₂ CF ₃ 4-FC ₆ H ₄ H
384 2,6-Cl ₂ CF ₃ 2,4-Cl ₂ -C ₆ H ₃ H
385 85 2,6-Cl ₂ CF ₃ 2,4-F ₂ -C ₆ H ₃ H
386 137 2,6-Cl ₂ CF ₃ 2,2-Me ₂ -3-Bu H
387 86 2,6-Cl ₂ CF ₃ 2,4,6-Me ₃ -C ₆ H ₂ H
388 173 2,6-Cl ₂ CF ₃ MeSCH ₂ C (CH ₃ ) ₂ H
389 148 2,6-Cl ₂ CF ₃ 2-MeOCO-3-C ₄ H ₂ SH
390 165 2,6-Cl ₂ CF ₃ 2- {CH ₃ CH (CH ₃ ) CH ₂ CH (CH ₃ )}-3-C ₄ H ₂ SH
391 78 2,6-Cl ₂ CF ₃ 4-t-Bu-C ₆ H ₄ CH ₂ H
392 79 2,6-Cl ₂ CF ₃ C ₆ H ₅ C (Me) HH
393 80 2,6-Cl ₂ CF ₃ Cumyl H
394 87 2,6-Cl ₂ CF ₃ EtO H
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Continuation of Table-1 ─────────────────────────────────
Compound Example No. No. Xn R ¹ R ³ R ⁴
─────────────────────────────────
395 88 2,6-Cl ₂ CF ₃ t-BuO H
396 159 2,6-Cl ₂ CF ₃ 2-s-Bu-C ₆ H ₄ H
397 156 2,6-Cl ₂ CF ₃ 2-t-Bu-C ₆ H ₄ H
398 157 2,6-Cl ₂ CF ₃ 2-IC ₆ H ₄ H
399 158 2,6-Cl ₂ CF ₃ 2-C ₆ H ₄ OC ₆ H ₄ H
400 169 2,6-Cl ₂ CF ₃ Cyclopropyl H
401 170 2,6-Cl ₂ CF ₃ Cyclopropyl Cyclohexyl
402 171 2,6-Cl ₂ CF ₃ Cyclopropyl i-Pr
403 68 2,6-Cl ₂ CF ₃ t-Bu Cyclohexyl
404 34 2,6-Cl ₂ C ₂ F ₅ Me H
405 152 2,6-Cl ₂ C ₂ F ₅ i-Pr i-Pr
406 27 3,4-Cl ₂ CF ₃ Me H
407 133 3,5-Cl ₂ CF ₃ t-Bu H
408 134 3,5-Cl ₂ CF ₃ 3-CN-3-Pentyl H
409 136 3,5-Cl ₂ CF ₃ i-Pr i-Pr
410 135 3,5-Cl ₂ CF ₃ t-Bu Et
411 166 2-Cl-6-CF CF ₃ t-Bu H
412 167 2-Cl-6-CF ₃ CF ₃ t-Bu Et
413 4-Cl-2-F CF ₃ HH
414 28 4-Cl-2-F CF ₃ Me H
415 4-Cl-2-F CF ₃ Me Me
416 4-Cl-2-F CF ₃ Me Et
417 4-Cl-2-F CF ₃ Et H
418 4-Cl-2-F CF ₃ Et Et
419 4-Cl-2-F CF ₃ Et Cyclohexyl
420 4-Cl-2-F CF ₃ Et C ₆ H ₅
421 4-Cl-2-F CF ₃ Et 4-FC ₆ H ₄
422 4-Cl-2-F CF ₃ Et 2,4-F ₂ -C ₆ H ₃
423 93 4-Cl-2-F CF ₃ Pr H
424 4-Cl-2-F CF ₃ i-Pr H
425 4-Cl-2-F CF ₃ i-Pr i-Pr
426 4-Cl-2-F CF ₃ i-Pr 4-FC ₆ H ₄
427 4-Cl-2-F CF ₃ i-Pr 2,4-F ₂ -C ₆ H ₃
428 4-Cl-2-F CF ₃ Bu H
429 4-Cl-2-F CF ₃ s-Bu H
430 4-Cl-2-F CF ₃ i-Bu H
431 4-Cl-2-F CF ₃ t-Bu H
432 4-Cl-2-F CF ₃ Hexyl H
433 4-Cl-2-F CF ₃ ClCH ₂ CH ₂ H
434 4-Cl-2-F CF ₃ BrCH ₂ CH ₂ H
435 4-Cl-2-F CF ₃ Tetrahydrofurfuryl H
436 4-Cl-2-F CF ₃ Allyl H
437 4-Cl-2-F CF ₃ Cyclopropyl H
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Continuation of Table-1 ─────────────────────────────────
Compound Example No. No. Xn R ¹ R ³ R ⁴
─────────────────────────────────
438 4-Cl-2-F CF ₃ Cyclohexyl H
439 4-Cl-2-F CF ₃ C ₆ H ₅ H
440 4-Cl-2-F CF ₃ 4-Cl-C ₆ H ₄ H
441 4-Cl-2-F CF ₃ 4-FC ₆ H ₄ H
442 4-Cl-2-F CF ₃ 2,4-Cl ₂ -C ₆ H ₃ H
443 4-Cl-2-F CF ₃ 2,4-F ₂ -C ₆ H ₃ H
444 4-Cl-2-F CF ₃ 4-t-Bu-C ₆ H ₄ CH ₂ H
445 4-Cl-2-F CHF ₂ EtO H
446 4-Cl-2-F CHF ₂ t-BuO H
447 2,4-F ₂ CF ₃ Me H
448 2,5-F ₂ CF ₃ Me H
449 2,6-F ₂ CHF ₂ Me H
450 2,6-F ₂ CHF ₂ Et H
451 2,6-F ₂ CHF ₂ i-Pr H
452 2,6-F ₂ CHF ₂ i-Pr 4-FC ₆ H ₄
453 2,6-F ₂ CHF ₂ i-Pr 2,4-F ₂ -C ₆ H ₃
454 2,6-F ₂ CHF ₂ Bu H
455 2,6-F ₂ CHF ₂ s-Bu H
456 2,6-F ₂ CHF ₂ i-Bu H
457 2,6-F ₂ CHF ₂ t-Bu H
458 2,6-F ₂ CHF ₂ Neopentyl H
459 2,6-F ₂ CHF ₂ t-Amyl H
460 2,6-F ₂ CHF ₂ Propargyl H
461 2,6-F ₂ CHF ₂ EtO H
462 2,6-F ₂ CHF ₂ t-BuO H
463 2,6-F ₂ CF ₃ HH
464 29 2,6-F ₂ CF ₃ Me H
465 2,6-F ₂ CF ₃ Me Me
466 2,6-F ₂ CF ₃ Me Et
467 2,6-F ₂ CF ₃ Et H
468 2,6-F ₂ CF ₃ Et Et
469 2,6-F ₂ CF ₃ Et Cyclohexyl
470 2,6-F ₂ CF ₃ Et C ₆ H ₅
471 2,6-F ₂ CF ₃ Et 4-FC ₆ H ₄
472 2,6-F ₂ CF ₃ Et 2,4-F ₂ -C ₆ H ₃
473 2,6-F ₂ CF ₃ Pr H
474 94 2,6-F ₂ CF ₃ i-Pr H
475 2,6-F ₂ CF ₃ i-Pr i-Pr
476 2,6-F ₂ CF ₃ i-Pr 4-FC ₆ H ₄
477 2,6-F ₂ CF ₃ i-Pr 2,4-F ₂ -C ₆ H ₃
478 2,6-F ₂ CF ₃ Bu H
479 95 2,6-F ₂ CF ₃ s-Bu H
480 2,6-F ₂ CF ₃ i-Bu H
─────────────────────────────────

Continuation of Table-1 ─────────────────────────────────
Compound Example No. No. Xn R ¹ R ³ R ⁴
─────────────────────────────────
481 96 2,6-F ₂ CF ₃ t-Bu H
482 149 2,6-F ₂ CF ₃ t-Bu Et
483 2,6-F ₂ CF ₃ Hexyl H
484 2,6-F ₂ CF ₃ ClCH ₂ CH ₂ H
485 2,6-F ₂ CF ₃ BrCH ₂ CH ₂ H
486 97 2,6-F ₂ CF ₃ NCCH ₂ H
487 2,6-F ₂ CF ₃ Tetrahydrofurfuryl H
488 98 2,6-F ₂ CF ₃ (CH ₃ ) ₂ CHC (CO ₂ Me) HH
489 2,6-F ₂ CF ₃ Allyl H
490 2,6-F ₂ CF ₃ Cyclopropyl H
491 2,6-F ₂ CF ₃ Cyclohexyl H
492 2,6-F ₂ CF ₃ C ₆ H ₅ H
493 2,6-F ₂ CF ₃ 4-Cl-C ₆ H ₄ H
494 99 2,6-F ₂ CF ₃ 2-FC ₆ H ₄ H
495 2,6-F ₂ CF ₃ 4-FC ₆ H ₄ H
496 2,6-F ₂ CF ₃ 2,4-Cl ₂ -C ₆ H ₃ H
497 2,6-F ₂ CF ₃ 2,4-F ₂ -C ₆ H ₃ H
498 2,6-F ₂ CF ₃ 4-t-Bu-C ₆ H ₄ CH ₂ H
499 2,6-F ₂ CF ₃ EtO H
500 2,6-F ₂ CF ₃ t-BuO H
501 31 4-Cl-5-cyclopentyloxy-2-F CF ₃ Me H
502 181 4-Cl-2-F-5-propargyloxy CF ₃ HH
503 32 4-Cl-2-F-5-propargyloxy CF ₃ Me H
504 179 2,6-Cl ₂ -4-CF ₃ CF ₃ HH
505 30 2,6-Cl ₂ -4-CF ₃ CF ₃ Me H
506 100 2,6-Cl ₂ -4-CF ₃ CF ₃ t-Bu H
507 150 2,6-Cl ₂ -4-CF ₃ CF ₃ t-Bu Et
508 180 2,6-Cl ₂ -4-CF ₃ O CF ₃ HH
509 101 2,6-Cl ₂ -4-CF ₃ O CF ₃ Propargyl H
510 2,6-Br ₂ -4-CF ₃ O CF ₃ Me H
511 2,6-Cl ₂ -4-CF ₃ O CF ₃ Me H
──────────────────────────────────────

────────────────────────
化合物 実施例
Ｎｏ. Ｎｏ. Ｘｎ Ｒ^１
────────────────────────
512 H CF₃
513 2-Me CF₃
514 3-Me CF₃
515 4-Me CF₃
516 2-t-Bu CF₃
517 3-t-Bu CF₃
518 183 4-t-Bu CF₃
519 2-CF₃ CF₃
520 3-CF₃ CF₃
521 4-CF₃ CF₃
522 2-CN CF₃
523 3-CN CF₃
524 4-CN CF₃
525 2-MeO CF₃
526 3-MeO CF₃
527 4-MeO CF₃
528 2-Br CF₃
528 3-Br CF₃
530 4-Br CF₃
531 2-Cl CF₃
532 3-Cl CF₃
533 4-Cl CF₃
534 2-F CF₃
535 3-F CF₃
536 4-F CF₃
537 2-NO₂ CF₃
538 3-NO₂ CF₃
539 4-NO₂ CF₃
540 2,3-Cl₂ CF₃
541 184 2,4-Cl₂ CF₃
542 3,4-Cl₂ CF₃
543 2,5-Cl₂ CF₃
544 182 2,6-Cl₂ CF₃
545 4-Cl-2-F CF₃
546 2,4-F₂ CF₃
547 2,5-F₂ CF₃
548 2,6-F₂ CF₃
549 187 4-Cl-5-cyclopentyloxy-2-F CF₃
550 188 4-Cl-2-F-5-propargyloxy CF₃
551 185 2,6-Cl₂-4-CF₃ CF₃
552 2,6-Br₂-4-CF₃O CF₃
553 186 2,6-Cl₂-4-CF₃O CF₃
─────────────────────────── Table 2 4-Cyano-5-trifluoromethylimidazole derivatives

────────────────────────
Compound Example No. No. Xn R ¹
────────────────────────
512 H CF ₃
513 2-Me CF ₃
514 3-Me CF ₃
515 4-Me CF ₃
516 2-t-Bu CF ₃
517 3-t-Bu CF ₃
518 183 4-t-Bu CF ₃
519 2-CF ₃ CF ₃
520 3-CF ₃ CF ₃
521 4-CF ₃ CF ₃
522 2-CN CF ₃
523 3-CN CF ₃
524 4-CN CF ₃
525 2-MeO CF ₃
526 3-MeO CF ₃
527 4-MeO CF ₃
528 2-Br CF ₃
528 3-Br CF ₃
530 4-Br CF ₃
531 2-Cl CF ₃
532 3-Cl CF ₃
533 4-Cl CF ₃
534 2-F CF ₃
535 3-F CF ₃
536 4-F CF ₃
537 2-NO ₂ CF ₃
538 3-NO ₂ CF ₃
539 4-NO ₂ CF ₃
540 2,3-Cl ₂ CF ₃
541 184 2,4-Cl ₂ CF ₃
542 3,4-Cl ₂ CF ₃
543 2,5-Cl ₂ CF ₃
544 182 2,6-Cl ₂ CF ₃
545 4-Cl-2-F CF ₃
546 2,4-F ₂ CF ₃
547 2,5-F ₂ CF ₃
548 2,6-F ₂ CF ₃
549 187 4-Cl-5-cyclopentyloxy-2-F CF ₃
550 188 4-Cl-2-F-5-propargyloxy CF ₃
551 185 2,6-Cl ₂ -4-CF ₃ CF ₃
552 2,6-Br ₂ -4-CF ₃ O CF ₃
553 186 2,6-Cl ₂ -4-CF ₃ O CF ₃
────────────────────────────

  Hereinafter, a method for formulating the imidazole derivative of the present invention as a herbicide will be described. However, the herbicide of the present invention is not limited to these formulation examples, and can be formulated by mixing with other various additives other than those exemplified in the following formulation examples at any ratio. .

Formulation Example-1 (Granule)
Water (15 parts by weight) is added to the compound of the present invention (1 part by weight), calcium lignin sulfonate (1 part by weight), lauryl sulfate (1 part by weight), bentonite (30 parts by weight) and talc (67 parts by weight). The mixture was kneaded with a kneader and then granulated with an extrusion granulator. This was dried with a fluid dryer to obtain granules containing 1% of the compound of the present invention as an active ingredient.

Formulation Example-2 (Flowable)
Compound of the present invention (20.0 parts by weight), sulfosuccinic acid di-2-ethylhexyl ester sodium salt (2.0 parts by weight), polyoxyethylene nonylphenyl ether (2.0 parts by weight), propylene glycol (5.0 parts by weight) Parts by weight), an antifoaming agent (0.5 parts by weight) and water (70.5 parts by weight) were uniformly mixed and pulverized by a wet ball mill to obtain a flowable agent containing 20% of the compound of the present invention as an active ingredient. .

Formulation Example-3 (Dry flowable agent)
Compound of the present invention (75 parts by weight), Isoban No. 1 [anionic surfactant: manufactured by Kuraray Isoprene Chemical Co., Ltd., trade name] (10 parts by weight), Vanillex N [anionic surfactant: Sanyo Kokusaku Pulp (Trade name) (5 parts by weight), white carbon (5 parts by weight) and clay (5 parts by weight) are uniformly mixed and pulverized to produce a dry flowable containing 75% of the compound of the present invention as an active ingredient. A (granular hydration) agent was obtained.

Formulation Example-4 (wettable powder)
Compound of the present invention (15 parts by weight), white carbon (15 parts by weight), calcium lignin sulfonate (3 parts by weight), polyoxyethylene nonylphenyl ether (2 parts by weight), diatomaceous earth (5 parts by weight) and clay (60 Parts by weight) were uniformly mixed by a pulverizing mixer to obtain a wettable powder containing 15% of the compound of the present invention as an active ingredient.

Formulation Example-5 (Emulsion)
The compound of the present invention (20 parts by weight), Solpol 700H [Emulsifier: Toho Chemical Co., Ltd., trade name] (20 parts by weight) and xylene (60 parts by weight) are mixed to give 20% of the compound of the present invention as an active ingredient. As an emulsion was obtained.

Formulation Example-6 (powder)
A compound of the present invention (0.5 parts by weight), white carbon (0.5 parts by weight), calcium stearate (0.5 parts by weight), clay (50.0 parts by weight) and talc (48.5 parts by weight). The resulting mixture was uniformly mixed and ground to obtain a powder containing 0.5% of the compound of the present invention as an active ingredient.
Next, the herbicidal effect of the compound of the present invention will be described with reference to test examples.

Test Example-1 Herbicidal effect test on paddy weeds and phytotoxicity test on transplanted rice paddy field fertilizer (N: P: K = 17) : 17: 17) was mixed, and scribing was performed. After that, 30 seeds of Tainubie, broad-leaved weeds (Azena, Konagi) and firefly seeds were sown on the soil surface. Furthermore, three rice plants at the two-leaf stage were transplanted as one strain per plant. The transplantation depth was 2 cm. Immediately after transplantation, the water was submerged and the water depth was maintained at about 3 cm. Subsequent management was performed in a glass greenhouse. One day after paddy rice transplantation, a wettable powder prepared from the compound of the present invention according to Formulation Example 4 was diluted with water, and a predetermined amount of the water-diluted drug solution was added dropwise.
This test was carried out in two consecutive systems per chemical concentration group, and the control effect on weeds and the phytotoxicity on crops were investigated 21 days after drug treatment. The survey method is to investigate the raw weight (g) of the weeds and transplanted rice remaining in the treated area and the raw weight (g) of the weeds and transplanted rice in the non-treated area. (%) Was calculated. The obtained results are shown in Table 3.

[Calculation formula (1) for herbicidal effect and phytotoxicity]
Herbicidal effect and phytotoxicity (%) = [1- (a / b)] × 100
(In the formula, a represents the raw weight (g) of weeds or crops in the treated area, and b represents the raw weight (g) of weeds or crops in the untreated area.)

Table-3 Herbicidal effect test on paddy weeds and phytotoxicity test on transplanted rice ──────────────────────────────────── ───
Compound Application rate Herbicidal effect Drug damage

No. kg / ha Nobie Konagi Azena Firefly Rice ──────────────────────────────────────
309 1.2 80 90 100 40 70
550 1.2 73 100 100 55 0
339 1.2 98 80 85 20 0
360 1.2 100 100 100 100 18
371 1.2 100 90 100 45 8
342 1.2 100 100 100 85 41
411 1.2 95 90 90 100 10
99 1.2 90 90 100 40 0
68 1.2 90 100 100 40 0
258 1.2 100 100 100 100 10
57 1.2 100 100 100 100 10
261 1.2 100 100 100 100 0
373 1.2 100 100 100 100 10
254 1.2 90 90 90 100 0
357 1.2 70 30 50 100 10
300 1.2 40 30 30 100 0
361 1.2 30 50 20 100 10
276 1.2 30 90 0 100 0
350 1.2 99 100 100 100 20
356 1.2 99 100 100 99 0
──────────────────────────────────────

Test Example-2 Herbicidal effect test on upland weeds and phytotoxicity test on crops (soil treatment test)
(1) Herbicidal effect test for field crop weeds: Field soil (alluvial loam) is packed in an unglazed pot with a size of 1 / 5,000 are, and 1 cm of surface soil and seeds of each weed (mesh shiba, enokorogusa, Inubiyu, Inuta) 50 grains each were mixed uniformly, and the surface layer was lightly pressed. The emulsion of the compound of the present invention prepared in accordance with Formulation Example-5 was diluted with water, and 1000 liters per hectare so that the application amount of the active ingredient was equivalent to 1.2 kg per hectare 2 days after sowing the water-diluted drug solution. Sprayed at a rate. This test was performed in triplicate. The weed control effect was investigated 30 days after the drug treatment. In the investigation method, the herbicidal effect (%) was obtained by the above calculation formula (1) by comparing the raw weight (g) of the weed remaining in the treated area with the raw weight (g) of the untreated area. The test results are shown in Table-10.

(2) Phytotoxicity test for crops Cultivate field soil (alluvial loam soil) in an unglazed pot with a size of 1 / 10,000 are, and deepen seeds of each crop (5 soybeans, 10 wheat) in separate pots. The seed layer was sown to 2 cm, and the surface layer was lightly pressed. The emulsion of the compound of the present invention prepared according to Formulation Example-5 was diluted with water, and the water diluted chemical solution was sprayed on the soil surface at a rate of 100 liters per 10 ares one day after sowing. When the application amount of the active ingredient was converted, it corresponded to 1.2 kg per hectare. The degree of chemical damage to each crop was investigated 30 days after drug treatment. In the investigation method, the crop phytotoxicity (%) was obtained by the above calculation formula (1) in comparison with the raw weight (g) of the crop in the treated area and the raw weight (g) of the untreated area. The test results are shown in Table-4.

Table 4 Herbicidal effect test on field weeds and phytotoxicity test on crops (soil treatment test)
──────────────────────────────────────
Compound Application rate Herbicidal effect Drug damage

No. kg / ha Bark beetle Enokorogusa Inubiyu Inutade Soybean Wheat ──────────────────────────────────────
218 1.2 90 100 100 100 0 0
115 1.2 98 90 100 100 40 0
406 1.2 100 100 100 100 15 15
360 1.2 100 99 100 93 5 95
371 1.2 100 100 100 90 0 0
118 1.2 80 85 100 100 10 0
286 1.2 80 85 100 100 40 40
342 1.2 100 100 99 95 95 70 70
411 1.2 100 100_30 0 40
261 1.2 100 92_80 10 30
332 1.2 99 100 100 90 10 10
506 1.2 100 90 _ 30 0 0
328 1.2 100 50 _ 0 0 0
327 1.2 100 100_30 0 0
350 1.2 100 100 95 93 20 30
337 1.2 100 100_50 0 20
──────────────────────────────────────

Test example-3 Herbicidal effect test on field weeds and phytotoxicity test on crops (stems and leaves treatment test) A field soil (alluvial loam) is packed in a Wagner pot with a size of 1/2 000 ares, 30 seeds of each weed seed were sown, the surface layer of about 1 cm of soil was mixed with these seeds, and the surface layer was lightly pressed. In addition, 10 different soybean and wheat seeds were sown in a depth of 2 cm in another pot similar to this. When each weed reached the 1st to 2nd leaf stage, soybean reached the 1st leaf stage, and wheat reached the 2nd leaf stage, the emulsion prepared with the compound of the present invention according to Formulation Example-5 was diluted with water to a predetermined concentration. After the adjustment, the diluted chemical solution was sprayed onto the weeds and crop foliage at a rate of 100 liters per 10 ares using a carbon dioxide gas sprayer. When the application amount of the active ingredient was converted, it corresponded to 1.2 kg per hectare. This test was performed in triplicate. 30 days after the chemical treatment, weed control effects and phytotoxicity on crops were investigated. The survey method is to calculate the herbicidal effect and phytotoxicity (%) by comparing the raw weight (g) of weeds and crops remaining in the treated area with the raw weight (g) of weeds and crops in the untreated area. ). These test results are shown in Table-5.

Table 5 Herbicidal effect test on upland weeds and phytotoxicity test on crops (stem and foliage treatment test)
──────────────────────────────────────
Compound Application rate Herbicidal effect Drug damage

No. kg / ha Bark beetle Enokorogusa Inubiyu Inutade Soybean Wheat ──────────────────────────────────────
281 1.2 60 75 100 70 0 0
351 1.2 95 100 100 100 0 0
439 1.2 100 100 100 100 30 0
324 1.2 95 90 90 95 40 83
333 1.2 95 90 93 92 40 0
105 1.2 100 100 95 100 100 0
260 1.2 100 100 100 100 100 100 100
310 1.2 98 90 95 90 90 95 75
──────────────────────────────────────

Claims (6)

General formula (1)

(In the formula, R ¹ represents a fluoroalkyl group having 1 to 6 carbon atoms. R ² represents an optionally substituted carbamoyl group, carboxy group, or cyano group. X represents a hydrogen atom, a halogen atom, or a carbon number of 1. -6 alkyl group, haloalkyl group having 1 to 6 carbon atoms, alkoxy group having 1 to 6 carbon atoms, haloalkoxy group having 1 to 6 carbon atoms, optionally substituted phenyloxy group, 1 to 6 carbon atoms Alkylthio group, haloalkylthio group having 1 to 6 carbon atoms, alkylsulfinyl group having 1 to 6 carbon atoms, haloalkylsulfinyl group having 1 to 6 carbon atoms, alkylsulfonyl group having 1 to 6 carbon atoms, haloalkyl having 1 to 6 carbon atoms Sulfonyl group, amino group, alkylamino group having 1 to 6 carbon atoms, di (alkyl having 1 to 6 carbon atoms) amino group, acylamino group having 1 to 6 carbon atoms, alkylsulfur group having 1 to 6 carbon atoms Nylamino group, hydroxyl group, mercapto group, carboxy group, cyano group or nitro group, n represents 0 or an integer of 1 to 5. However, when n is an integer of 2 to 5, X may be the same or different. Good imidazole derivative. R ² is a —CONR ³ R ⁴ group (wherein R ³ and R ⁴ are each independently a hydrogen atom, an optionally substituted alkyl group having 1 to 12 carbon atoms, or an optionally substituted carbon number 3). A cycloalkyl group having 8 to 8 carbon atoms, an alkenyl group having 3 to 6 carbon atoms which may be substituted, an alkynyl group having 3 to 6 carbon atoms which may be substituted, and an aralkyl having 7 to 11 carbon atoms which may be substituted A group, an optionally substituted phenyl group, an optionally substituted alkyl group having 1 to 12 carbon atoms or an optionally substituted aralkyloxy group having 7 to 11 carbon atoms, or R ³ and R ⁴ is an optionally substituted carbamoyl group or a cyano group, which may form an optionally substituted heterocyclic ring together with the nitrogen atom to which it is bonded. Imidazole derivatives. General formula (2)

(Wherein R ¹ , X and n represent the same meaning as described above. R ⁵ represents an alkyl group having 1 to 6 carbon atoms.) The ester moiety of the imidazole derivative represented by the general formula (3 )

(Wherein R ¹ , X and n represent the same meaning as described above), and then reacted with a halogenating agent to produce a compound represented by the general formula (4)

(Wherein R ¹ , X and n represent the same meaning as described above, Y represents a halogen atom), and then the general formula (5)

(Wherein R ³ and R ⁴ represent the same meaning as described above), the amines represented by the general formula (6)

(Wherein R ¹ , R ³ , R ⁴ , X and n represent the same meaning as described above). General formula (2)

(Wherein R ¹ , R ⁵ , X and n represent the same meaning as described above) and the general formula (7)

Wherein R ^3a is a hydrogen atom, an optionally substituted alkyl group having 1 to 12 carbon atoms, an optionally substituted cycloalkyl group having 3 to 8 carbon atoms, or an optionally substituted carbon number 3 -6 alkenyl group, optionally substituted alkynyl group having 3 to 6 carbon atoms, optionally substituted aralkyl group having 7 to 11 carbon atoms, optionally substituted phenyl group, optionally substituted A suitable alkoxy group having 1 to 12 carbon atoms or an optionally substituted aralkyloxy group having 7 to 11 carbon atoms) is optionally reacted in the presence of a base to give a general formula (6a )

(Wherein R ¹ , R ^3a , X and n represent the same meaning as described above). General formula (6b)

(Wherein R ¹ , X and n represent the same meaning as described above) are reacted in the presence of a dehydrating agent to give a general formula (8)

(Wherein R ¹ , X and n represent the same meaning as described above). General formula (1a)

[Wherein R ¹ , X and n represent the same meaning as described above. R ^2a represents an optionally substituted carbamoyl group represented by a —CONR ³ R ⁴ group (R ³ and R ⁴ have the same meaning as described above), or a cyano group. ] The herbicide which uses the imidazole derivative shown by this as an active ingredient.