JP2010270065A - Compound bearing optically active trifluoromethyl group, manufacturing method for the same, and manufacturing method for optically active amines bearing trifluoromethyl group using the same - Google Patents

Compound bearing optically active trifluoromethyl group, manufacturing method for the same, and manufacturing method for optically active amines bearing trifluoromethyl group using the same Download PDF

Info

Publication number
JP2010270065A
JP2010270065A JP2009123457A JP2009123457A JP2010270065A JP 2010270065 A JP2010270065 A JP 2010270065A JP 2009123457 A JP2009123457 A JP 2009123457A JP 2009123457 A JP2009123457 A JP 2009123457A JP 2010270065 A JP2010270065 A JP 2010270065A
Authority
JP
Japan
Prior art keywords
oxopyrazolidine
dimethyl
ethyl
trifluoro
naphthyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
JP2009123457A
Other languages
Japanese (ja)
Other versions
JP5495618B2 (en
Inventor
Tetsuo Shibata
哲男 柴田
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Nagoya Institute of Technology NUC
Tosoh F Tech Inc
Original Assignee
Nagoya Institute of Technology NUC
Tosoh F Tech Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Nagoya Institute of Technology NUC, Tosoh F Tech Inc filed Critical Nagoya Institute of Technology NUC
Priority to JP2009123457A priority Critical patent/JP5495618B2/en
Publication of JP2010270065A publication Critical patent/JP2010270065A/en
Application granted granted Critical
Publication of JP5495618B2 publication Critical patent/JP5495618B2/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Landscapes

  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

<P>PROBLEM TO BE SOLVED: To provide a novel optically active 3-oxopyrazolidine derivative bearing a trifluoromethyl group, and a manufacturing method for optically active amines using the same. <P>SOLUTION: The optically active 3-oxopyrazolidine derivative is represented by general formula (1). The manufacturing method for the optically active amines bearing a trifluoromethyl group comprises ring-opening the oxopyrazolidine derivative by a reduction catalyst followed by an acid treatment. In the formula, R<SP>1</SP>and R<SP>2</SP>are each a hydrogen atom or 1-4C alkyl, and R<SP>3</SP>is 1-10C alkyl, optionally substituted phenyl, optionally substituted 1-naphthyl, optionally substituted 2-naphthyl, optionally substituted arylethylenyl, or optionally substituted arylalkyl. <P>COPYRIGHT: (C)2011,JPO&INPIT

Description

本発明は、光学活性トリフルオロメチル基含有化合物、その製造方法並びにそれを用いたトリフルオロメチル基含有光学活性アミン類の製造方法に関する。光学活性なトリフルオロメチル基を含有するアミン類は医農薬の合成中間体として有用な化合物である。   The present invention relates to an optically active trifluoromethyl group-containing compound, a production method thereof, and a production method of a trifluoromethyl group-containing optically active amine using the same. Amines containing an optically active trifluoromethyl group are useful compounds as intermediates for the synthesis of medicines and agrochemicals.

光学活性トリフルオロメチル基含有化合物の製造方法としては、キラル触媒存在下、トリフルオシリルトリフルオロメタンを用い、カルボニル化合物への不斉トリフルオロメチル化反応により、トリフルオロメチル基を含有する光学活性なアルコール類の製造方法は知られている(非特許文献1、2)。   As an optically active trifluoromethyl group-containing compound production method, an optically active alcohol containing a trifluoromethyl group by asymmetric trifluoromethylation reaction to a carbonyl compound using trifluorosilyltrifluoromethane in the presence of a chiral catalyst. The manufacturing method of a kind is known (nonpatent literature 1, 2).

Toru;T., et. al., Tetrahedron, 63, 35(2007), 8521-8528。Toru; T., Et. Al., Tetrahedron, 63, 35 (2007), 8521-8528. Toru;T., et. al., Org. Lrtt., 2007, 9(18), 3707-3710。Toru; T., et. Al., Org. Lrtt., 2007, 9 (18), 3707-3710.

従来の非特許文献1に記載の方法はカルボニル化合物への不斉トリフルオロメチル化反応は可能であるが、カルボニル等価体のイミン類への付加反応は、触媒反応で進行せず、高価なキラル触媒が大量に必要で工業的な製法とは言えなかった。   Although the conventional method described in Non-Patent Document 1 enables an asymmetric trifluoromethylation reaction to a carbonyl compound, the addition reaction of a carbonyl equivalent to an imine does not proceed by a catalytic reaction, and an expensive chiral A large amount of catalyst was required, and it was not an industrial process.

本発明者は、触媒量のキラル化合物を用い、イミン類の不斉トリフルオロメチル化を実施する方法について鋭意検討した結果、3−オキソピラゾリジン誘導体とアルデヒド類より誘導される3−オキソピラゾリジン N,N−ベタイン誘導体(アゾメチンイミン)を反応基質として用いることにより、不斉触媒反応とすることが可能となり、新規な光学活性なトリフルオロメチル基付加体が高光学選択性で得られることを見出した。さらに得られたトリフルオロメチル基付加体は、スポンジニッケル等の還元触媒による開環、引き続き酸で処理することによりトリフルオロメチル基を含有する光学活性アミン類の製造が可能であることを見出し、本発明を完成させるに至った。   As a result of intensive investigations on a method for carrying out asymmetric trifluoromethylation of imines using a catalytic amount of a chiral compound, the present inventor has found that 3-oxopyrazolidine derivatives and 3-oxopyra derived from aldehydes. By using a zolidine N, N-betaine derivative (azomethine imine) as a reaction substrate, an asymmetric catalytic reaction can be achieved, and a novel optically active trifluoromethyl group adduct can be obtained with high optical selectivity. I found out. Furthermore, the obtained trifluoromethyl group adduct was found to be capable of producing optically active amines containing a trifluoromethyl group by ring-opening with a reduction catalyst such as sponge nickel and subsequent treatment with an acid. The present invention has been completed.

すなわち本発明は、
[1] 下記一般式(1)
That is, the present invention
[1] The following general formula (1)

(式中、R及びRはそれぞれ独立に水素原子又は炭素数1〜4のアルキル基を示し、Rは炭素数1〜10のアルキル基、置換基を有しても良いフェニル基、置換基を有しても良い1−ナフチル基、置換基を有しても良い2−ナフチル基、置換基を有しても良いアリールエチレニル基又は置換基を有しても良いアリールアルキルを示す)
で表される光学活性3−オキソピラゾリジン誘導体。
(In the formula, R 1 and R 2 each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, R 3 represents an alkyl group having 1 to 10 carbon atoms, an optionally substituted phenyl group, 1-naphthyl group which may have a substituent, 2-naphthyl group which may have a substituent, arylethylenyl group which may have a substituent or arylalkyl which may have a substituent Show)
An optically active 3-oxopyrazolidine derivative represented by the formula:

[項2] 下記一般式(2) [Claim 2] The following general formula (2)

(式中R、R及びRは前記に同じ)
で表される3−オキソピラゾリジン N,N−ベタイン誘導体とトリメチルシリルトリフルオロメタンをキラル相間移動触媒及び塩基の存在下、反応させることを特徴とする項1に記載された一般式(1)で表される光学活性3−オキソピラゾリジン誘導体の製造方法。
(Wherein R 1 , R 2 and R 3 are the same as above)
Wherein the 3-oxopyrazolidine N, N-betaine derivative represented by the formula (3) is reacted with trimethylsilyltrifluoromethane in the presence of a chiral phase transfer catalyst and a base. A process for producing the optically active 3-oxopyrazolidine derivative represented.

[項3] 項2において、キラル相間移動触媒が下記一般式(3) [Item 3] In item 2, the chiral phase transfer catalyst is represented by the following general formula (3):

(式中Rは水素原子またはメトキシ基、Rは水素原子または4−メチルフェニルスルホニルメチル基、Rはエチル基またはエチレニル基、R及びRは各々独立して、水素原子、メチル基、エチル基、iso−プロピル基、tert−ブチル基、メトキシ基、エトキシ基、iso−プロポキシ基、tert−ブトキシ基、フェニル基、3,5−ビス(トリフルオロメチル)フェニル基、1−ナフチル基を示し、Xは塩素原子または臭素原子を示す)
で表されることを特徴とする項2に記載の3−オキソピラゾリジン誘導体の製造方法。
Wherein R 4 is a hydrogen atom or a methoxy group, R 5 is a hydrogen atom or a 4-methylphenylsulfonylmethyl group, R 6 is an ethyl group or an ethylenyl group, R 7 and R 8 are each independently a hydrogen atom, methyl Group, ethyl group, iso-propyl group, tert-butyl group, methoxy group, ethoxy group, iso-propoxy group, tert-butoxy group, phenyl group, 3,5-bis (trifluoromethyl) phenyl group, 1-naphthyl A group, X represents a chlorine atom or a bromine atom)
Item 3. A process for producing a 3-oxopyrazolidine derivative according to Item 2, wherein

[項4] 項1に記載された一般式(1)で表される光学活性3−オキソピラゾリジン誘導体を還元触媒で開環した後、酸で処理することを特徴とする下記一般式(4) [Item 4] The optically active 3-oxopyrazolidine derivative represented by the general formula (1) described in the item 1 is ring-opened with a reduction catalyst and then treated with an acid. 4)

(Rは前記に同じ)
で表される光学活性アミン類の製造方法を提供するものである。
(R 3 is the same as above)
The manufacturing method of optically active amines represented by these is provided.

本発明により、光学活性3−オキソピラゾリジン N,N−ベタイン誘導体及びその触媒的不斉反応による製法を提供することができた。また得られる光学活性3−オキソピラゾリジン N,N−ベタイン誘導体より医農薬中間体原料として有用な光学活性アミン類の製法を提供することができた。   According to the present invention, it was possible to provide an optically active 3-oxopyrazolidine N, N-betaine derivative and a production method based on a catalytic asymmetric reaction thereof. Further, it was possible to provide a method for producing optically active amines useful as raw materials for intermediates for pharmaceuticals and agricultural chemicals from the obtained optically active 3-oxopyrazolidine N, N-betaine derivatives.

以下、本発明を詳細に説明する。   Hereinafter, the present invention will be described in detail.

一般式(1)、一般式(2)のR、Rにおける炭素数1〜4のアルキル基とは炭素数1〜4の直鎖若しくは分岐鎖のアルキル基であり、例えばメチル基、エチル基、n−プロピル基、iso−プロピル基、n−ブチル基、sec−ブチル基、tert−ブチル基などを挙げることができる。 Formula (1), the alkyl group having 1 to 4 carbon atoms in R 1, R 2 in the general formula (2) is an alkyl group having a linear or branched chain of 1 to 4 carbon atoms, such as methyl group, ethyl Group, n-propyl group, iso-propyl group, n-butyl group, sec-butyl group, tert-butyl group and the like.

一般式(1)、一般式(2)のRにおける炭素数1〜10のアルキル基とは、炭素数1〜10の直鎖若しくは分岐鎖のアルキル基又は炭素数3〜10の環状アルキル基であり、例えばメチル基、エチル基、n−プロピル基、iso−プロピル基、シクロプロピル基、n−ブチル基、iso−ブチル基、tert−ブチル基、n−ペンチル基、シクロペンチル基、n−ヘキシル基、シクロヘキシル基、n−ヘプチル基、シクロヘプチル基、4−メチルシクロヘキシル基、n−オクチル基、n−ノニル基、n−デシル基等などを挙げることができる。 The C1-C10 alkyl group in R < 3 > of General formula (1) and General formula (2) is a C1-C10 linear or branched alkyl group or a C3-C10 cyclic alkyl group For example, methyl group, ethyl group, n-propyl group, iso-propyl group, cyclopropyl group, n-butyl group, iso-butyl group, tert-butyl group, n-pentyl group, cyclopentyl group, n-hexyl Group, cyclohexyl group, n-heptyl group, cycloheptyl group, 4-methylcyclohexyl group, n-octyl group, n-nonyl group, n-decyl group and the like.

一般式(1)、一般式(2)のRにおける置換基を有しても良いフェニル基とは、無置換またはベンゼン環上の任意の水素が1〜5置換されたフェニル基であり、置換基としては、フッ素原子、塩素原子、臭素原子、メチル基、エチル基、炭素数3〜10の直鎖、分岐もしくは環状のアルキル基、メトキシ基、エトキシ基または炭素数3〜10の直鎖、分岐もしくは環状のアルキルオキシ基等を挙げることができる。 The phenyl group which may have a substituent in R 3 of the general formula (1) and the general formula (2) is a phenyl group which is unsubstituted or substituted with 1 to 5 arbitrary hydrogens on the benzene ring, Examples of the substituent include a fluorine atom, a chlorine atom, a bromine atom, a methyl group, an ethyl group, a straight chain having 3 to 10 carbon atoms, a branched or cyclic alkyl group, a methoxy group, an ethoxy group, or a straight chain having 3 to 10 carbon atoms. And a branched or cyclic alkyloxy group.

一般式(1)、一般式(2)のRにおける置換基を有しても良い1−ナフチル基とは、無置換またはナフチル環上の任意の水素が1〜7置換された1−ナフチル基であり、置換基としてはフッ素原子、塩素原子、臭素原子、メチル基、エチル基、炭素数3〜10の直鎖、分岐もしくは環状のアルキル基、メトキシ基、エトキシ基または炭素数3〜10の直鎖、分岐もしくは環状のアルキルオキシ基等を挙げることができる。 The 1-naphthyl group which may have a substituent in R 3 of the general formula (1) or the general formula (2) is 1-naphthyl which is unsubstituted or substituted with 1 to 7 arbitrary hydrogens on the naphthyl ring. The substituent is a fluorine atom, chlorine atom, bromine atom, methyl group, ethyl group, linear, branched or cyclic alkyl group having 3 to 10 carbon atoms, methoxy group, ethoxy group, or 3 to 10 carbon atoms. And a linear, branched or cyclic alkyloxy group.

一般式(1)、一般式(2)のRにおける置換基を有しても良い2−ナフチル基とは、無置換またはナフチル環上の任意の水素が1〜7置換された2−ナフチル基であり、置換基としてはフッ素原子、塩素原子、臭素原子、メチル基、エチル基、炭素数3〜10の直鎖、分岐もしくは環状のアルキル基、メトキシ基、エトキシ基または炭素数3〜10の直鎖、分岐もしくは環状のアルキルオキシ基等を挙げることができる。 The 2-naphthyl group which may have a substituent in R 3 of the general formula (1) or the general formula (2) is an unsubstituted or 2-naphthyl in which any hydrogen on the naphthyl ring is substituted by 1 to 7 The substituent is a fluorine atom, chlorine atom, bromine atom, methyl group, ethyl group, linear, branched or cyclic alkyl group having 3 to 10 carbon atoms, methoxy group, ethoxy group, or 3 to 10 carbon atoms. And a linear, branched or cyclic alkyloxy group.

一般式(1)、一般式(2)のRにおける置換基を有しても良いアリールエチレニル基とは、2−フェニルエチレニル基、2−(2−メチルフェニル)エチレニル基、2−(3−メチルフェニル)エチレニル基、2−(4−メチルフェニル)エチレニル基、2−(2−エチルフェニル)エチレニル基、2−(3−エチルフェニル)エチレニル基、2−(4−エチルフェニル)エチレニル基、2−(2−n−プロピルフェニル)エチレニル基、2−(3−n−プロピルフェニル)エチレニル基、2−(4−n−プロピルフェニル)エチレニル基、2−(2−n−ブチルフェニル)エチレニル基、2−(3−n−ブチルフェニル)エチレニル基、2−(4−n−ブチルフェニル)エチレニル基、2−(2−sec−ブチルフェニル)エチレニル基、2−(3−sec−ブチルフェニル)エチレニル基、2−(4−sec−ブチルフェニル)エチレニル基、2−(2−tert−ブチルフェニル)エチレニル基、2−(3−tert−ブチルフェニル)エチレニル基、2−(4−tert−ブチルフェニル)エチレニル基、2−(2−メトキシフェニル)エチレニル基、2−(3−メトキシフェニル)エチレニル基、2−(4−メトキシフェニル)エチレニル基、2−(2−エトキシフェニル)エチレニル基、2−(3−エトキシフェニル)エチレニル基、2−(4−エトキシフェニル)エチレニル基、2−(2−n−プロポキシフェニル)エチレニル基、2−(3−n−プロポキシフェニル)エチレニル基、2−(4−n−プロポキシフェニル)エチレニル基、2−(2−n−ブトキシフェニル)エチレニル基、2−(3−n−ブトキシフェニル)エチレニル基、2−(4−n−ブトキシフェニル)エチレニル基、2−(2−sec−ブトキシフェニル)エチレニル基、2−(3−sec−ブトキシフェニル)エチレニル基、2−(4−sec−ブトキシフェニル)エチレニル基、2−(2−tert−ブトキシフェニル)エチレニル基、2−(3−tert−ブトキシフェニル)エチレニル基、2−(4−tert−ブトキシフェニル)エチレニル基、2−(2−フルオロフェニル)エチレニル基、2−(3−フルオロフェニル)エチレニル基、2−(4−フルオロフェニル)エチレニル基、2−(2−クロロフェニル)エチレニル基、2−(3−クロロフェニル)エチレニル基、2−(4−クロロフェニル)エチレニル基、2−(2−ブロモフェニル)エチレニル基、2−(3−ブロモフェニル)エチレニル基、2−(4−ブロモフェニル)エチレニル基、2−(2−シアノフェニル)エチレニル基、2−(3−シアノフェニル)エチレニル基、2−(4−シアノフェニル)エチレニル基、2−(2−ニトロフェニル)エチレニル基、2−(3−ニトロフェニル)エチレニル基、2−(4−ニトロフェニル)エチレニル基等を挙げることができる。 The arylethylenyl group which may have a substituent in R 3 of the general formula (1) and general formula (2) is a 2-phenylethylenyl group, a 2- (2-methylphenyl) ethylenyl group, 2- (3-methylphenyl) ethylenyl group, 2- (4-methylphenyl) ethylenyl group, 2- (2-ethylphenyl) ethylenyl group, 2- (3-ethylphenyl) ethylenyl group, 2- (4-ethylphenyl) Ethylenyl group, 2- (2-n-propylphenyl) ethylenyl group, 2- (3-n-propylphenyl) ethylenyl group, 2- (4-n-propylphenyl) ethylenyl group, 2- (2-n-butyl) Phenyl) ethylenyl group, 2- (3-n-butylphenyl) ethylenyl group, 2- (4-n-butylphenyl) ethylenyl group, 2- (2-sec-butylphenyl) ethylenyl Group, 2- (3-sec-butylphenyl) ethylenyl group, 2- (4-sec-butylphenyl) ethylenyl group, 2- (2-tert-butylphenyl) ethylenyl group, 2- (3-tert-butylphenyl) ) Ethylenyl group, 2- (4-tert-butylphenyl) ethylenyl group, 2- (2-methoxyphenyl) ethylenyl group, 2- (3-methoxyphenyl) ethylenyl group, 2- (4-methoxyphenyl) ethylenyl group, 2- (2-ethoxyphenyl) ethylenyl group, 2- (3-ethoxyphenyl) ethylenyl group, 2- (4-ethoxyphenyl) ethylenyl group, 2- (2-n-propoxyphenyl) ethylenyl group, 2- (3 -N-propoxyphenyl) ethylenyl group, 2- (4-n-propoxyphenyl) ethylenyl group, 2- (2-n-butoxy) Phenyl) ethylenyl group, 2- (3-n-butoxyphenyl) ethylenyl group, 2- (4-n-butoxyphenyl) ethylenyl group, 2- (2-sec-butoxyphenyl) ethylenyl group, 2- (3-sec -Butoxyphenyl) ethylenyl group, 2- (4-sec-butoxyphenyl) ethylenyl group, 2- (2-tert-butoxyphenyl) ethylenyl group, 2- (3-tert-butoxyphenyl) ethylenyl group, 2- (4 -Tert-butoxyphenyl) ethylenyl group, 2- (2-fluorophenyl) ethylenyl group, 2- (3-fluorophenyl) ethylenyl group, 2- (4-fluorophenyl) ethylenyl group, 2- (2-chlorophenyl) ethylenyl Group, 2- (3-chlorophenyl) ethylenyl group, 2- (4-chlorophenyl) ethylenyl 2- (2-bromophenyl) ethylenyl group, 2- (3-bromophenyl) ethylenyl group, 2- (4-bromophenyl) ethylenyl group, 2- (2-cyanophenyl) ethylenyl group, 2- (3- Cyanophenyl) ethylenyl group, 2- (4-cyanophenyl) ethylenyl group, 2- (2-nitrophenyl) ethylenyl group, 2- (3-nitrophenyl) ethylenyl group, 2- (4-nitrophenyl) ethylenyl group, etc. Can be mentioned.

置換基を有しても良いアリールアルキルとは、ベンジル基、2−フェニルエチル基、3−フェニルプロピル基、4−フェニルブチル基、5−フェニルペンチル基、2−メチルベンジル基、2−(2−メチルフェニル)エチル基、3−(2−メチルフェニル)プロピル基、4−(2−メチルフェニル)ブチル基、5−(2−メチルフェニル)ペンチル基、2−(3−メチルフェニル)エチル基、3−(3−メチルフェニル)プロピル基、4−(3−メチルフェニル)ブチル基、5−(3−メチルフェニル)ペンチル基、2−(4−メチルフェニル)エチル基、3−(4−メチルフェニル)プロピル基、4−(4−メチルフェニル)ブチル基、5−(4−メチルフェニル)ペンチル基、2−エチルベンジル基、2−(2−エチルフェニル)エチル基、3−(2−エチルフェニル)プロピル基、4−(2−エチルフェニル)ブチル基、5−(2−エチルフェニル)ペンチル基、2−(3−エチルフェニル)エチル基、3−(3−エチルフェニル)プロピル基、4−(3−エチルフェニル)ブチル基、5−(3−エチルフェニル)ペンチル基、2−(4−エチルフェニル)エチル基、3−(4−エチルフェニル)プロピル基、4−(4−エチルフェニル)ブチル基、5−(4−エチルフェニル)ペンチル基、2−n−プロピルベンジル基、2−(2−n−プロピルフェニル)エチル基、3−(2−n−プロピルフェニル)プロピル基、4−(2−n−プロピルフェニル)ブチル基、5−(2−n−プロピルフェニル)ペンチル基、2−(3−n−プロピルフェニル)エチル基、3−(3−n−プロピルフェニル)プロピル基、4−(3−n−プロピルフェニル)ブチル基、5−(3−n−プロピルフェニル)ペンチル基、2−(4−n−プロピルフェニル)エチル基、3−(4−n−プロピルフェニル)プロピル基、4−(4−n−プロピルフェニル)ブチル基、5−(4−n−プロピルフェニル)ペンチル基、2−iso−プロピルベンジル基、2−(2−iso−プロピルフェニル)エチル基、3−(2−iso−プロピルフェニル)プロピル基、4−(2−iso−プロピルフェニル)ブチル基、5−(2−iso−プロピルフェニル)ペンチル基、2−(3−iso−プロピルフェニル)エチル基、3−(3−iso−プロピルフェニル)プロピル基、4−(3−iso−プロピルフェニル)ブチル基、5−(3−iso−プロピルフェニル)ペンチル基、2−(4−iso−プロピルフェニル)エチル基、3−(4−iso−プロピルフェニル)プロピル基、4−(4−iso−プロピルフェニル)ブチル基、5−(4−iso−プロピルフェニル)ペンチル基、2−n−ブチルベンジル基、2−(2−n−ブチルフェニル)エチル基、3−(2−n−ブチルフェニル)プロピル基、4−(2−n−ブチルフェニル)ブチル基、5−(2−n−ブチルフェニル)ペンチル基、2−(3−n−ブチルフェニル)エチル基、3−(3−n−ブチルフェニル)プロピル基、4−(3−n−ブチルフェニル)ブチル基、5−(3−n−ブチルフェニル)ペンチル基、2−(4−n−ブチルフェニル)エチル基、3−(4−n−ブチルフェニル)プロピル基、4−(4−n−ブチルフェニル)ブチル基、5−(4−n−ブチルフェニル)ペンチル基、2−(2−iso−ブチルフェニル)エチル基、3−(2−iso−ブチルフェニル)プロピル基、4−(2−iso−ブチルフェニル)ブチル基、5−(2−iso−ブチルフェニル)ペンチル基、2−(3−iso−ブチルフェニル)エチル基、3−(3−iso−ブチルフェニル)プロピル基、4−(3−iso−ブチルフェニル)ブチル基、5−(3−iso−ブチルフェニル)ペンチル基、2−(4−iso−ブチルフェニル)エチル基、3−(4−iso−ブチルフェニル)プロピル基、4−(4−iso−ブチルフェニル)ブチル基、5−(4−iso−ブチルフェニル)ペンチル基、2−tert−ブチルベンジル基、2−(2−tert−ブチルフェニル)エチル基、3−(2−tert−ブチルフェニル)プロピル基、4−(2−tert−ブチルフェニル)ブチル基、5−(2−tert−ブチルフェニル)ペンチル基、2−(3−tert−ブチルフェニル)エチル基、3−(3−tert−ブチルフェニル)プロピル基、4−(3−tert−ブチルフェニル)ブチル基、5−(3−tert−ブチルフェニル)ペンチル基、2−(4−tert−ブチルフェニル)エチル基、3−(4−tert−ブチルフェニル)プロピル基、4−(4−tert−ブチルフェニル)ブチル基、5−(4−tert−ブチルフェニル)ペンチル基、2−メトキシベンジル基、2−(2−メトキシフェニル)エチル基、3−(2−メトキシフェニル)プロピル基、4−(2−メトキシフェニル)ブチル基、5−(2−メトキシフェニル)ペンチル基、2−(3−メトキシフェニル)エチル基、3−(3−メトキシフェニル)プロピル基、4−(3−メトキシフェニル)ブチル基、5−(3−メトキシフェニル)ペンチル基、2−(4−メトキシフェニル)エチル基、3−(4−メトキシフェニル)プロピル基、4−(4−メトキシフェニル)ブチル基、5−(4−メトキシフェニル)ペンチル基、2−エトキシベンジル基、2−(2−エトキシフェニル)エチル基、3−(2−エトキシフェニル)プロピル基、4−(2−エトキシフェニル)ブチル基、5−(2−エトキシフェニル)ペンチル基、2−(3−エトキシフェニル)エチル基、3−(3−エトキシフェニル)プロピル基、4−(3−エトキシフェニル)ブチル基、5−(3−エトキシフェニル)ペンチル基、2−(4−エトキシフェニル)エチル基、3−(4−エトキシフェニル)プロピル基、4−(4−エトキシフェニル)ブチル基、5−(4−エトキシフェニル)ペンチル基、2−n−プロポキシベンジル基、2−(2−n−プロポシキフェニル)エチル基、3−(2−n−プロポキシフェニル)プロピル基、4−(2−n−プロポキシフェニル)ブチル基、5−(2−n−プロポキシフェニル)ペンチル基、2−(3−n−プロポキシフェニル)エチル基、3−(3−n−プロポキシフェニル)プロピル基、4−(3−n−プロポキシフェニル)ブチル基、5−(3−n−プロポキシフェニル)ペンチル基、2−(4−n−プロポキシフェニル)エチル基、3−(4−n−プロポキシフェニル)プロピル基、4−(4−n−プロポキシフェニル)ブチル基、5−(4−n−プロポキシフェニル)ペンチル基、2−iso−プロポキシベンジル基、2−(2−iso−プロポキシフェニル)エチル基、3−(2−iso−プロポキシフェニル)プロピル基、4−(2−iso−プロポキシフェニル)ブチル基、5−(2−iso−プロポキシフェニル)ペンチル基、2−(3−iso−プロポキシフェニル)エチル基、3−(3−iso−プロポキシフェニル)プロピル基、4−(3−iso−プロポキシフェニル)ブチル基、5−(3−iso−プロポキシフェニル)ペンチル基、2−(4−iso−プロポキシフェニル)エチル基、3−(4−iso−プロポキシフェニル)プロピル基、4−(4−iso−プロポキシフェニル)ブチル基、5−(4−iso−プロポキシフェニル)ペンチル基、2−n−ブトキシベンジル基、2−(2−n−ブトキシフェニル)エチル基、3−(2−n−ブトキシフェニル)プロピル基、4−(2−n−ブトキシフェニル)ブチル基、5−(2−n−ブトキシフェニル)ペンチル基、2−(3−n−ブトキシフェニル)エチル基、3−(3−n−ブトキシフェニル)プロピル基、4−(3−n−ブトキシフェニル)ブチル基、5−(3−n−ブトキシフェニル)ペンチル基、2−(4−n−ブトキシフェニル)エチル基、3−(4−n−ブトキシフェニル)プロピル基、4−(4−n−ブトキシフェニル)ブチル基、5−(4−n−ブトキシフェニル)ペンチル基、2−(2−iso−ブトキシフェニル)エチル基、3−(2−iso−ブトキシフェニル)プロピル基、4−(2−iso−ブトキシフェニル)ブチル基、5−(2−iso−ブトキシフェニル)ペンチル基、2−(3−iso−ブトキシフェニル)エチル基、3−(3−iso−ブトキシフェニル)プロピル基、4−(3−iso−ブトキシフェニル)ブチル基、5−(3−iso−ブトキシフェニル)ペンチル基、2−(4−iso−ブトキシフェニル)エチル基、3−(4−iso−ブトキシフェニル)プロピル基、4−(4−iso−ブトキシフェニル)ブチル基、5−(4−iso−ブトキシフェニル)ペンチル基、2−tert−ブトキシベンジル基、2−(2−tert−ブトキシフェニル)エチル基、3−(2−tert−ブトキシフェニル)プロピル基、4−(2−tert−ブトキシフェニル)ブチル基、5−(2−tert−ブトキシフェニル)ペンチル基、2−(3−tert−ブトキシフェニル)エチル基、3−(3−tert−ブトキシフェニル)プロピル基、4−(3−tert−ブトキシフェニル)ブチル基、5−(3−tert−ブトキシフェニル)ペンチル基、2−(4−tert−ブトキシフェニル)エチル基、3−(4−tert−ブトキシフェニル)プロピル基、4−(4−tert−ブトキシフェニル)ブチル基、5−(4−tert−ブトキシフェニル)ペンチル基、2−フルオロベンジル基、2−(2−フルオロフェニル)エチル基、3−(2−フルオロフェニル)プロピル基、4−(2−フルオロフェニル)ブチル基、5−(2−フルオロフェニル)ペンチル基、2−(3−フルオロフェニル)エチル基、3−(3−フルオロフェニル)プロピル基、4−(3−フルオロフェニル)ブチル基、5−(3−フルオロフェニル)ペンチル基、2−(4−フルオロフェニル)エチル基、3−(4−フルオロフェニル)プロピル基、4−(4−フルオロフェニル)ブチル基、5−(4−フルオロフェニル)ペンチル基、2−クロロベンジル基、2−(2−クロロフェニル)エチル基、3−(2−クロロフェニル)プロピル基、4−(2−クロロフェニル)ブチル基、5−(2−クロロフェニル)ペンチル基、2−(3−クロロフェニル)エチル基、3−(3−クロロフェニル)プロピル基、4−(3−クロロフェニル)ブチル基、5−(3−クロロフェニル)ペンチル基、2−(4−クロロフェニル)エチル基、3−(4−クロロフェニル)プロピル基、4−(4−クロロフェニル)ブチル基、5−(4−クロロフェニル)ペンチル基、2−ブロモベンジル基、2−(2−ブロモフェニル)エチル基、3−(2−ブロモフェニル)プロピル基、4−(2−ブロモフェニル)ブチル基、5−(2−ブロモフェニル)ペンチル基、2−(3−ブロモフェニル)エチル基、3−(3−ブロモフェニル)プロピル基、4−(3−ブロモフェニル)ブチル基、5−(3−ブロモフェニル)ペンチル基、2−(4−ブロモフェニル)エチル基、3−(4−ブロモフェニル)プロピル基、4−(4−ブロモフェニル)ブチル基、5−(4−ブロモフェニル)ペンチル基、2−シアノベンジル基、2−(2−シアノフェニル)エチル基、3−(2−シアノフェニル)プロピル基、4−(2−シアノフェニル)ブチル基、5−(2−シアノフェニル)ペンチル基、2−(3−シアノフェニル)エチル基、3−(3−シアノフェニル)プロピル基、4−(3−シアノフェニル)ブチル基、5−(3−シアノフェニル)ペンチル基、2−(4−シアノフェニル)エチル基、3−(4−シアノフェニル)プロピル基、4−(4−シアノフェニル)ブチル基、5−(4−シアノフェニル)ペンチル基、2−ニトロベンジル基、2−(2−ニトロフェニル)エチル基、3−(2−ニトロフェニル)プロピル基、4−(2−ニトロフェニル)ブチル基、5−(2−ニトロフェニル)ペンチル基、2−(3−ニトロフェニル)エチル基、3−(3−ニトロフェニル)プロピル基、4−(3−ニトロフェニル)ブチル基、5−(3−ニトロフェニル)ペンチル基、2−(4−ニトロフェニル)エチル基、3−(4−ニトロフェニル)プロピル基、4−(4−ニトロフェニル)ブチル基、5−(4−ニトロフェニル)ペンチル基等を挙げることができる。   The arylalkyl which may have a substituent is benzyl, 2-phenylethyl, 3-phenylpropyl, 4-phenylbutyl, 5-phenylpentyl, 2-methylbenzyl, 2- (2 -Methylphenyl) ethyl group, 3- (2-methylphenyl) propyl group, 4- (2-methylphenyl) butyl group, 5- (2-methylphenyl) pentyl group, 2- (3-methylphenyl) ethyl group 3- (3-methylphenyl) propyl group, 4- (3-methylphenyl) butyl group, 5- (3-methylphenyl) pentyl group, 2- (4-methylphenyl) ethyl group, 3- (4- Methylphenyl) propyl group, 4- (4-methylphenyl) butyl group, 5- (4-methylphenyl) pentyl group, 2-ethylbenzyl group, 2- (2-ethylphenyl) ethyl 3- (2-ethylphenyl) propyl group, 4- (2-ethylphenyl) butyl group, 5- (2-ethylphenyl) pentyl group, 2- (3-ethylphenyl) ethyl group, 3- (3- Ethylphenyl) propyl group, 4- (3-ethylphenyl) butyl group, 5- (3-ethylphenyl) pentyl group, 2- (4-ethylphenyl) ethyl group, 3- (4-ethylphenyl) propyl group, 4- (4-ethylphenyl) butyl group, 5- (4-ethylphenyl) pentyl group, 2-n-propylbenzyl group, 2- (2-n-propylphenyl) ethyl group, 3- (2-n- Propylphenyl) propyl group, 4- (2-n-propylphenyl) butyl group, 5- (2-n-propylphenyl) pentyl group, 2- (3-n-propylphenyl) ethyl group, 3- (3- n Propylphenyl) propyl group, 4- (3-n-propylphenyl) butyl group, 5- (3-n-propylphenyl) pentyl group, 2- (4-n-propylphenyl) ethyl group, 3- (4- n-propylphenyl) propyl group, 4- (4-n-propylphenyl) butyl group, 5- (4-n-propylphenyl) pentyl group, 2-iso-propylbenzyl group, 2- (2-iso-propyl) Phenyl) ethyl group, 3- (2-iso-propylphenyl) propyl group, 4- (2-iso-propylphenyl) butyl group, 5- (2-iso-propylphenyl) pentyl group, 2- (3-iso) -Propylphenyl) ethyl group, 3- (3-iso-propylphenyl) propyl group, 4- (3-iso-propylphenyl) butyl group, 5- (3-iso- Propylphenyl) pentyl group, 2- (4-iso-propylphenyl) ethyl group, 3- (4-iso-propylphenyl) propyl group, 4- (4-iso-propylphenyl) butyl group, 5- (4- iso-propylphenyl) pentyl group, 2-n-butylbenzyl group, 2- (2-n-butylphenyl) ethyl group, 3- (2-n-butylphenyl) propyl group, 4- (2-n-butyl) Phenyl) butyl group, 5- (2-n-butylphenyl) pentyl group, 2- (3-n-butylphenyl) ethyl group, 3- (3-n-butylphenyl) propyl group, 4- (3-n -Butylphenyl) butyl group, 5- (3-n-butylphenyl) pentyl group, 2- (4-n-butylphenyl) ethyl group, 3- (4-n-butylphenyl) propyl group, 4- (4 -N Butylphenyl) butyl group, 5- (4-n-butylphenyl) pentyl group, 2- (2-iso-butylphenyl) ethyl group, 3- (2-iso-butylphenyl) propyl group, 4- (2- iso-butylphenyl) butyl group, 5- (2-iso-butylphenyl) pentyl group, 2- (3-iso-butylphenyl) ethyl group, 3- (3-iso-butylphenyl) propyl group, 4- ( 3-iso-butylphenyl) butyl group, 5- (3-iso-butylphenyl) pentyl group, 2- (4-iso-butylphenyl) ethyl group, 3- (4-iso-butylphenyl) propyl group, 4 -(4-iso-butylphenyl) butyl group, 5- (4-iso-butylphenyl) pentyl group, 2-tert-butylbenzyl group, 2- (2-tert-butyl) Phenyl) ethyl group, 3- (2-tert-butylphenyl) propyl group, 4- (2-tert-butylphenyl) butyl group, 5- (2-tert-butylphenyl) pentyl group, 2- (3-tert) -Butylphenyl) ethyl group, 3- (3-tert-butylphenyl) propyl group, 4- (3-tert-butylphenyl) butyl group, 5- (3-tert-butylphenyl) pentyl group, 2- (4 -Tert-butylphenyl) ethyl group, 3- (4-tert-butylphenyl) propyl group, 4- (4-tert-butylphenyl) butyl group, 5- (4-tert-butylphenyl) pentyl group, 2- Methoxybenzyl group, 2- (2-methoxyphenyl) ethyl group, 3- (2-methoxyphenyl) propyl group, 4- (2-methoxyphenyl) ) Butyl group, 5- (2-methoxyphenyl) pentyl group, 2- (3-methoxyphenyl) ethyl group, 3- (3-methoxyphenyl) propyl group, 4- (3-methoxyphenyl) butyl group, 5- (3-methoxyphenyl) pentyl group, 2- (4-methoxyphenyl) ethyl group, 3- (4-methoxyphenyl) propyl group, 4- (4-methoxyphenyl) butyl group, 5- (4-methoxyphenyl) Pentyl group, 2-ethoxybenzyl group, 2- (2-ethoxyphenyl) ethyl group, 3- (2-ethoxyphenyl) propyl group, 4- (2-ethoxyphenyl) butyl group, 5- (2-ethoxyphenyl) Pentyl group, 2- (3-ethoxyphenyl) ethyl group, 3- (3-ethoxyphenyl) propyl group, 4- (3-ethoxyphenyl) butyl group, 5- ( -Ethoxyphenyl) pentyl group, 2- (4-ethoxyphenyl) ethyl group, 3- (4-ethoxyphenyl) propyl group, 4- (4-ethoxyphenyl) butyl group, 5- (4-ethoxyphenyl) pentyl group 2-n-propoxybenzyl group, 2- (2-n-propoxyphenyl) ethyl group, 3- (2-n-propoxyphenyl) propyl group, 4- (2-n-propoxyphenyl) butyl group, 5 -(2-n-propoxyphenyl) pentyl group, 2- (3-n-propoxyphenyl) ethyl group, 3- (3-n-propoxyphenyl) propyl group, 4- (3-n-propoxyphenyl) butyl group , 5- (3-n-propoxyphenyl) pentyl group, 2- (4-n-propoxyphenyl) ethyl group, 3- (4-n-propoxyphenyl) propyl 4- (4-n-propoxyphenyl) butyl group, 5- (4-n-propoxyphenyl) pentyl group, 2-iso-propoxybenzyl group, 2- (2-iso-propoxyphenyl) ethyl group, 3- (2-iso-propoxyphenyl) propyl group, 4- (2-iso-propoxyphenyl) butyl group, 5- (2-iso-propoxyphenyl) pentyl group, 2- (3-iso-propoxyphenyl) ethyl group, 3- (3-iso-propoxyphenyl) propyl group, 4- (3-iso-propoxyphenyl) butyl group, 5- (3-iso-propoxyphenyl) pentyl group, 2- (4-iso-propoxyphenyl) ethyl Group, 3- (4-iso-propoxyphenyl) propyl group, 4- (4-iso-propoxyphenyl) butyl group, 5 -(4-iso-propoxyphenyl) pentyl group, 2-n-butoxybenzyl group, 2- (2-n-butoxyphenyl) ethyl group, 3- (2-n-butoxyphenyl) propyl group, 4- (2 -N-butoxyphenyl) butyl group, 5- (2-n-butoxyphenyl) pentyl group, 2- (3-n-butoxyphenyl) ethyl group, 3- (3-n-butoxyphenyl) propyl group, 4- (3-n-butoxyphenyl) butyl group, 5- (3-n-butoxyphenyl) pentyl group, 2- (4-n-butoxyphenyl) ethyl group, 3- (4-n-butoxyphenyl) propyl group, 4- (4-n-butoxyphenyl) butyl group, 5- (4-n-butoxyphenyl) pentyl group, 2- (2-iso-butoxyphenyl) ethyl group, 3- (2-iso-butoxyv) Nyl) propyl group, 4- (2-iso-butoxyphenyl) butyl group, 5- (2-iso-butoxyphenyl) pentyl group, 2- (3-iso-butoxyphenyl) ethyl group, 3- (3-iso -Butoxyphenyl) propyl group, 4- (3-iso-butoxyphenyl) butyl group, 5- (3-iso-butoxyphenyl) pentyl group, 2- (4-iso-butoxyphenyl) ethyl group, 3- (4 -Iso-butoxyphenyl) propyl group, 4- (4-iso-butoxyphenyl) butyl group, 5- (4-iso-butoxyphenyl) pentyl group, 2-tert-butoxybenzyl group, 2- (2-tert- Butoxyphenyl) ethyl group, 3- (2-tert-butoxyphenyl) propyl group, 4- (2-tert-butoxyphenyl) butyl , 5- (2-tert-butoxyphenyl) pentyl group, 2- (3-tert-butoxyphenyl) ethyl group, 3- (3-tert-butoxyphenyl) propyl group, 4- (3-tert-butoxyphenyl) Butyl group, 5- (3-tert-butoxyphenyl) pentyl group, 2- (4-tert-butoxyphenyl) ethyl group, 3- (4-tert-butoxyphenyl) propyl group, 4- (4-tert-butoxy group) Phenyl) butyl group, 5- (4-tert-butoxyphenyl) pentyl group, 2-fluorobenzyl group, 2- (2-fluorophenyl) ethyl group, 3- (2-fluorophenyl) propyl group, 4- (2 -Fluorophenyl) butyl group, 5- (2-fluorophenyl) pentyl group, 2- (3-fluorophenyl) ethyl group, 3- (3-fluorophenyl) propyl group, 4- (3-fluorophenyl) butyl group, 5- (3-fluorophenyl) pentyl group, 2- (4-fluorophenyl) ethyl group, 3- (4-fluorophenyl) Propyl group, 4- (4-fluorophenyl) butyl group, 5- (4-fluorophenyl) pentyl group, 2-chlorobenzyl group, 2- (2-chlorophenyl) ethyl group, 3- (2-chlorophenyl) propyl group 4- (2-chlorophenyl) butyl group, 5- (2-chlorophenyl) pentyl group, 2- (3-chlorophenyl) ethyl group, 3- (3-chlorophenyl) propyl group, 4- (3-chlorophenyl) butyl group 5- (3-chlorophenyl) pentyl group, 2- (4-chlorophenyl) ethyl group, 3- (4-chlorophenyl) propyl group, 4- 4-chlorophenyl) butyl group, 5- (4-chlorophenyl) pentyl group, 2-bromobenzyl group, 2- (2-bromophenyl) ethyl group, 3- (2-bromophenyl) propyl group, 4- (2- Bromophenyl) butyl group, 5- (2-bromophenyl) pentyl group, 2- (3-bromophenyl) ethyl group, 3- (3-bromophenyl) propyl group, 4- (3-bromophenyl) butyl group, 5- (3-bromophenyl) pentyl group, 2- (4-bromophenyl) ethyl group, 3- (4-bromophenyl) propyl group, 4- (4-bromophenyl) butyl group, 5- (4-bromo Phenyl) pentyl group, 2-cyanobenzyl group, 2- (2-cyanophenyl) ethyl group, 3- (2-cyanophenyl) propyl group, 4- (2-cyanophenyl) butyl group 5- (2-cyanophenyl) pentyl group, 2- (3-cyanophenyl) ethyl group, 3- (3-cyanophenyl) propyl group, 4- (3-cyanophenyl) butyl group, 5- (3-cyano Phenyl) pentyl group, 2- (4-cyanophenyl) ethyl group, 3- (4-cyanophenyl) propyl group, 4- (4-cyanophenyl) butyl group, 5- (4-cyanophenyl) pentyl group, 2 -Nitrobenzyl group, 2- (2-nitrophenyl) ethyl group, 3- (2-nitrophenyl) propyl group, 4- (2-nitrophenyl) butyl group, 5- (2-nitrophenyl) pentyl group, 2 -(3-nitrophenyl) ethyl group, 3- (3-nitrophenyl) propyl group, 4- (3-nitrophenyl) butyl group, 5- (3-nitrophenyl) pentyl group, 2- (4-nitrate) (Rophenyl) ethyl group, 3- (4-nitrophenyl) propyl group, 4- (4-nitrophenyl) butyl group, 5- (4-nitrophenyl) pentyl group and the like.

本発明の、前記一般式(1)で表される光学活性3−オキソピラゾリジン誘導体として、Rがメチル基、エチル基、炭素数3〜10の直鎖、分岐若しくは環式のアルキル基であるものとしては、具体的には例えば、(S)−1−(1,1,1−トリフルオロ−2−プロピル)−3−オキソピラゾリジン、(S)−1−(1,1,1−トリフルオロ−2−ブチル)−3−オキソピラゾリジン、(S)−1−(1,1,1−トリフルオロ−2−ペンチル)−3−オキソピラゾリジン、(S)−1−(1,1,1−トリフルオロ−3−メチル−2−ブチル)−3−オキソピラゾリジン、(S)−1−(1,1,1−トリフルオロ−2−ヘキシル)−3−オキソピラゾリジン、(S)−1−(1,1,1−トリフルオロ−3,3−ジメチル−2−ブチレン)−3−オキソピラゾリジン、(S)−1−(1,1,1−トリフルオロ−2−ヘプチル)−3−オキソピラゾリジン、(S)−1−(1,1,1−トリフルオロ−2−オクチル)−3−オキソピラゾリジン、(S)−1−(1,1,1−トリフルオロ−3−シクロヘキシル−2−エチル)−3−オキソピラゾリン、(S)−1−(1,1,1−トリフルオロ−2−ノニル)−3−オキソピラゾリジン、(S)−1−(1,1,1−トリフルオロ−2−デシル)−3−オキソピラゾリジン、(S)−1−(1,1,1−トリフルオロ−2−ウンデシル)−3−オキソピラゾリジン、(S)−1−(1,1,1−トリフルオロ−2−ドデシル)−3−オキソピラゾリジン等を挙げることができる。 In the present invention, as the optically active 3-oxopyrazolidine derivative represented by the general formula (1), R 3 is a methyl group, an ethyl group, a linear, branched or cyclic alkyl group having 3 to 10 carbon atoms. Specifically, for example, (S) -1- (1,1,1-trifluoro-2-propyl) -3-oxopyrazolidine, (S) -1- (1,1) , 1-trifluoro-2-butyl) -3-oxopyrazolidine, (S) -1- (1,1,1-trifluoro-2-pentyl) -3-oxopyrazolidine, (S)- 1- (1,1,1-trifluoro-3-methyl-2-butyl) -3-oxopyrazolidine, (S) -1- (1,1,1-trifluoro-2-hexyl) -3 -Oxopyrazolidine, (S) -1- (1,1,1-trifluoro-3,3-dimethyl-2-butylene) -3-oxopyrazolidine, (S) -1- (1,1,1-trifluoro-2-heptyl) -3-oxopyrazolidine, (S) -1- (1,1,1-tri Fluoro-2-octyl) -3-oxopyrazolidine, (S) -1- (1,1,1-trifluoro-3-cyclohexyl-2-ethyl) -3-oxopyrazoline, (S) -1- ( 1,1,1-trifluoro-2-nonyl) -3-oxopyrazolidine, (S) -1- (1,1,1-trifluoro-2-decyl) -3-oxopyrazolidine, ( S) -1- (1,1,1-trifluoro-2-undecyl) -3-oxopyrazolidine, (S) -1- (1,1,1-trifluoro-2-dodecyl) -3- And oxopyrazolidine.

本発明の、前記一般式(1)で表される光学活性3−オキソピラゾリジン誘導体として、Rが置換基を有しても良いフェニル基であるものとしては、具体的には例えば、(S)−1−(2,2,2−トリフルオロ−1−フェニル−1−エチル)−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−メチルフェニル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−メチルフェニル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−メチルフェニル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−エチルフェニル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−エチルフェニル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−エチルフェニル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−n−プロピルフェニル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−n−プロピルフェニル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−プロピルフェニル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−iso−プロピルフェニル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−iso−プロピルフェニル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−iso−プロピルフェニル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−n−ブチルフェニル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−n−ブチルフェニル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−ブチルフェニル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−iso−ブチルフェニル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−iso−ブチルフェニル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−iso−ブチルフェニル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−tert−ブチルフェニル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−tert−ブチルフェニル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−tert−ブチルフェニル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−ペンチルフェニル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−ヘキシルフェニル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−ヘプチルフェニル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−オクチルフェニル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−ノニルフェニル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−デシルフェニル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−メトキシフェニル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−メトキシフェニル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−メトキシフェニル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−エトキシフェニル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−エトキシフェニル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−エトキシフェニル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−n−プロポキシフェニル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−n−プロポキシフェニル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−プロポキシフェニル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−iso−プロポキシフェニル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−iso−プロポキシフェニル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−iso−プロポキシフェニル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−n−ブトキシフェニル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−n−ブトキシフェニル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−ブトキシフェニル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−iso−ブトキシフェニル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−iso−ブトキシフェニル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−iso−ブトキシフェニル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−tert−ブトキシフェニル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−tert−ブトキシフェニル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−tert−ブトキシフェニル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−ペントキシフェニル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−ヘキシルオキシフェニル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−ヘプチルオキシフェニル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−オクチルオキシフェニル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−ノニルオキシフェニル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−デシルオキシフェニル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−フルオロフェニル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−フルオロフェニル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−フルオロフェニル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−クロロフェニル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−クロロフェニル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−クロロフェニル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−ブロモフェニル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−ブロモフェニル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−ブロモフェニル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−シアノフェニル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−シアノフェニル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−シアノフェニル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−ニトロフェニル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−ニトロフェニル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−ニトロフェニル)−1−エチル]−3−オキソピラゾリジン等を挙げることができる。 Specific examples of the optically active 3-oxopyrazolidine derivative represented by the general formula (1) of the present invention in which R 3 is a phenyl group which may have a substituent include: (S) -1- (2,2,2-trifluoro-1-phenyl-1-ethyl) -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (2-Methylphenyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (3-methylphenyl) -1-ethyl] -3 -Oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-methylphenyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [ 2,2,2-trifluoro-1- (2-ethylphenyl) -1-ethyl] -3-oxopyrazolid (S) -1- [2,2,2-trifluoro-1- (3-ethylphenyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2, 2-trifluoro-1- (4-ethylphenyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (2-n-propyl) Phenyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (3-n-propylphenyl) -1-ethyl] -3-oxo Pyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-n-propylphenyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [ 2,2,2-trifluoro-1- (2-iso-propylphenyl) -1-ethyl] -3-oxopyrazolidine (S) -1- [2,2,2-trifluoro-1- (3-iso-propylphenyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2, 2-trifluoro-1- (4-iso-propylphenyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (2-n -Butylphenyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (3-n-butylphenyl) -1-ethyl] -3 -Oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-n-butylphenyl) -1-ethyl] -3-oxopyrazolidine, (S) -1 -[2,2,2-trifluoro-1- (2-iso-butylphenyl) -1-ethyl] -3-oxopi Zolidine, (S) -1- [2,2,2-trifluoro-1- (3-iso-butylphenyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2, 2,2-trifluoro-1- (4-iso-butylphenyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (2 -Tert-butylphenyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (3-tert-butylphenyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-tert-butylphenyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-n-pentylphenyl) -1-e Til] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-n-hexylphenyl) -1-ethyl] -3-oxopyrazolidine, ( S) -1- [2,2,2-trifluoro-1- (4-n-heptylphenyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2 -Trifluoro-1- (4-n-octylphenyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-n- Nonylphenyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-n-decylphenyl) -1-ethyl] -3- Oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (2-methoxyphenyl) -1-eth ] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (3-methoxyphenyl) -1-ethyl] -3-oxopyrazolidine, (S)- 1- [2,2,2-trifluoro-1- (4-methoxyphenyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1 -(2-Ethoxyphenyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (3-ethoxyphenyl) -1-ethyl]- 3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-ethoxyphenyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (2-n-propoxyphenyl) -1-ethyl] -3-o Sopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (3-n-propoxyphenyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2, 2,2-trifluoro-1- (4-n-propoxyphenyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (2 -Iso-propoxyphenyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (3-iso-propoxyphenyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-iso-propoxyphenyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (2-n-butoxypheny L) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (3-n-butoxyphenyl) -1-ethyl] -3-oxo Pyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-n-butoxyphenyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [ 2,2,2-trifluoro-1- (2-iso-butoxyphenyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (3-iso-butoxyphenyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-iso-butoxyphenyl) -1- Ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (2- ert-butoxyphenyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (3-tert-butoxyphenyl) -1-ethyl]- 3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-tert-butoxyphenyl) -1-ethyl] -3-oxopyrazolidine, (S)- 1- [2,2,2-trifluoro-1- (4-n-pentoxyphenyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-tri Fluoro-1- (4-n-hexyloxyphenyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-n-heptyl) Oxyphenyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- 2,2,2-trifluoro-1- (4-n-octyloxyphenyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1 -(4-n-nonyloxyphenyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-n-decyloxyphenyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (2-fluorophenyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (3-fluorophenyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2- Trifluoro-1- (4-fluorophenyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (2-chlorophenyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1 -(3-Chlorophenyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-chlorophenyl) -1-ethyl] -3- Oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (2-bromophenyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2 , 2,2-trifluoro-1- (3-bromophenyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4- Bromophenyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro -1- (2-cyanophenyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (3-cyanophenyl) -1-ethyl ] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-cyanophenyl) -1-ethyl] -3-oxopyrazolidine, (S)- 1- [2,2,2-trifluoro-1- (2-nitrophenyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1 -(3-Nitrophenyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-nitrophenyl) -1-ethyl]- 3-oxopyrazolidine and the like can be mentioned.

本発明の、前記一般式(1)で表される光学活性3−オキソピラゾリジン誘導体として、Rが置換基を有しても良い1−ナフチル基であるものとしては、具体的には例えば、(S)−1−[2,2,2−トリフルオロ−1−(1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−メチル−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−メチル−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−メチル−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−メチル−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−メチル−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−メチル−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−メチル−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−エチル−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−エチル−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−エチル−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−エチル−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−エチル−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−エチル−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−エチル−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−n−プロピル−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−n−プロピル−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−プロピル−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−n−プロピル−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−プロピル−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−n−プロピル−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−プロピル−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−iso−プロピル−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−iso−プロピル−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−iso−プロピル−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−iso−プロピル−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−iso−プロピル−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−iso−プロピル−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−iso−プロピル−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−n−ブチル−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−n−ブチル−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−ブチル−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−n−ブチル−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−ブチル−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−n−ブチル−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−ブチル−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−iso−ブチル−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−iso−ブチル−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−iso−ブチル−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−iso−ブチル−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−iso−ブチル−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−iso−ブチル−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−iso−ブチル−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−tert−ブチル−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−tert−ブチル−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−tert−ブチル−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−tert−ブチル−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−tert−ブチル−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−tert−ブチル−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−tert−ブチル−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−n−ペンチル−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−ペンチル−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−ペンチル−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−ペンチル−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−n−ヘキシル−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−ヘキシル−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−ヘキシル−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−ヘキシル−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−n−ヘプチル−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−ヘプチル−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−ヘプチル−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−ヘプチル−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−n−オクチル−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−オクチル−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−オクチル−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−オクチル−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−n−ノニル−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−ノニル−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−ノニル−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−ノニル−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−n−デシル−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−デシル−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−デシル−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−デシル−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−メトキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−メトキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−メトキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−メトキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−メトキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−メトキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−メトキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−エトキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−エトキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−エトキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−エトキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−エトキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフ
ルオロ−1−(7−エトキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−エトキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−n−プロポキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−n−プロポキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−プロポキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−n−プロポキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−プロポキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−n−プロポキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−プロポキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−iso−プロポキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−iso−プロポキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−iso−プロポキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−iso−プロポキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−iso−プロポキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−iso−プロポキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−iso−プロポキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−n−ブトキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−n−ブトキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−ブトキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−n−ブトキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−ブトキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−n−ブトキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−ブトキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−iso−ブトキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−iso−ブトキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−iso−ブトキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−iso−ブトキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−iso−ブトキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−iso−ブトキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−iso−ブトキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−tert−ブトキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−tert−ブトキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−tert−ブトキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−tert−ブトキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−tert−ブトキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−tert−ブトキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−tert−ブトキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−n−ペントキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−ペントキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−ペントキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−ペントキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−n−ヘキシルオキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−ヘキシルオキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−ヘキシルオキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−ヘキシルオキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−n−ヘプチルオキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−ヘプチルオキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−ヘプチルオキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−ヘプチルオキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−n−オクチルオキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−オクチルオキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−オクチルオキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−オクチルオキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−n−ノニルオキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−ノニルオキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−ノニルオキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−ノニルオキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−n−デシルオキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−デシルオキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−デシルオキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−デシルオキシ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−フルオロ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−フルオロ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−フルオロ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−フルオロ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−フルオロ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−フルオロ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−フルオロ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−クロロ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−クロロ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−クロロ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−クロロ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−クロロ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−クロロ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−クロロ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−ブロモ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−ブロモ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−ブロモ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−ブロモ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−ブロモ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−ブロモ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−ブロモ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−シアノ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−シアノ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−シアノ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−シアノ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフ
ルオロ−1−(6−シアノ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−シアノ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−シアノ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−ニトロ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−ニトロ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−ニトロ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−ニトロ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−ニトロ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−ニトロ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−ニトロ−1−ナフチル)−1−エチル]−3−オキソピラゾリジン等を挙げることができる。
As the optically active 3-oxopyrazolidine derivative represented by the general formula (1) of the present invention, R 3 Specific examples of the 1-naphthyl group which may have a substituent include (S) -1- [2,2,2-trifluoro-1- (1-naphthyl) -1 -Ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (2-methyl-1-naphthyl) -1-ethyl] -3-oxopyrazolidine (S) -1- [2,2,2-trifluoro-1- (3-methyl-1-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2, 2,2-trifluoro-1- (4-methyl-1-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- ( 5-methyl-1-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- 6-methyl-1-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (7-methyl-1-naphthyl) -1 -Ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (8-methyl-1-naphthyl) -1-ethyl] -3-oxopyrazolidine (S) -1- [2,2,2-trifluoro-1- (2-ethyl-1-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2, 2,2-trifluoro-1- (3-ethyl-1-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- ( 4-ethyl-1-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro 1- (5-ethyl-1-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (6-ethyl-1-naphthyl) ) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (7-ethyl-1-naphthyl) -1-ethyl] -3-oxo Pyrazolidine, (S) -1- [2,2,2-trifluoro-1- (8-ethyl-1-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (2-n-propyl-1-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-tri Fluoro-1- (3-n-propyl-1-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2, 2-trifluoro-1- (4-n-propyl-1-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- ( 5-n-propyl-1-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (6-n-propyl-1- Naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (7-n-propyl-1-naphthyl) -1-ethyl]- 3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (8-n-propyl-1-naphthyl) -1-ethyl] -3-oxopyrazolidine, ( S) -1- [2,2,2-trifluoro-1- (2-iso-propyl-1-naphthyl) -1-ethyl]- -Oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (3-iso-propyl-1-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S ) -1- [2,2,2-trifluoro-1- (4-iso-propyl-1-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2 , 2-trifluoro-1- (5-iso-propyl-1-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (6-iso-propyl-1-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (7-iso-propyl-1) -Naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trif Oro-1- (8-iso-propyl-1-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (2-n -Butyl-1-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (3-n-butyl-1-naphthyl)- 1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-n-butyl-1-naphthyl) -1-ethyl] -3-oxo Pyrazolidine, (S) -1- [2,2,2-trifluoro-1- (5-n-butyl-1-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S)- 1- [2,2,2-trifluoro-1- (6-n-butyl-1-naphthyl) -1-ethyl] -3-oxopyrazolidine (S) -1- [2,2,2-trifluoro-1- (7-n-butyl-1-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [ 2,2,2-trifluoro-1- (8-n-butyl-1-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro -1- (2-iso-butyl-1-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (3-iso- Butyl-1-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-iso-butyl-1-naphthyl) -1 -Ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (5-iso-butyl-1-na Til) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (6-iso-butyl-1-naphthyl) -1-ethyl]- 3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (7-iso-butyl-1-naphthyl) -1-ethyl] -3-oxopyrazolidine, ( S) -1- [2,2,2-trifluoro-1- (8-iso-butyl-1-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2, 2,2-trifluoro-1- (2-tert-butyl-1-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1 -(3-tert-butyl-1-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [ , 2,2-trifluoro-1- (4-tert-butyl-1-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro- 1- (5-tert-butyl-1-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (6-tert-butyl) -1-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (7-tert-butyl-1-naphthyl) -1- Ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (8-tert-butyl-1-naphthyl) -1-ethyl] -3-oxopyrazo Lysine, (S) -1- [2,2,2-trifluoro-1- (2-n-pentyl-1-naphth Til) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-n-pentyl-1-naphthyl) -1-ethyl]- 3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (6-n-pentyl-1-naphthyl) -1-ethyl] -3-oxopyrazolidine, ( S) -1- [2,2,2-trifluoro-1- (8-n-pentyl-1-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2, 2,2-trifluoro-1- (2-n-hexyl-1-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1 -(4-n-hexyl-1-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-tri Fluoro-1- (6-n-hexyl-1-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (8-n -Hexyl-1-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (2-n-heptyl-1-naphthyl)- 1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-n-heptyl-1-naphthyl) -1-ethyl] -3-oxo Pyrazolidine, (S) -1- [2,2,2-trifluoro-1- (6-n-heptyl-1-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S)- 1- [2,2,2-trifluoro-1- (8-n-heptyl-1-naphthyl) -1-ethyl] -3-oxopi Zolidine, (S) -1- [2,2,2-trifluoro-1- (2-n-octyl-1-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-n-octyl-1-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-tri Fluoro-1- (6-n-octyl-1-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (8-n -Octyl-1-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (2-n-nonyl-1-naphthyl)- 1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-n-nonyl-1-na Butyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (6-n-nonyl-1-naphthyl) -1-ethyl]- 3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (8-n-nonyl-1-naphthyl) -1-ethyl] -3-oxopyrazolidine, ( S) -1- [2,2,2-trifluoro-1- (2-n-decyl-1-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2, 2,2-trifluoro-1- (4-n-decyl-1-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1 -(6-n-decyl-1-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro 1- (8-n-decyl-1-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (2-methoxy-1) -Naphtyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (3-methoxy-1-naphthyl) -1-ethyl] -3 -Oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-methoxy-1-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S)- 1- [2,2,2-trifluoro-1- (5-methoxy-1-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-tri Fluoro-1- (6-methoxy-1-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2, , 2-trifluoro-1- (7-methoxy-1-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (8 -Methoxy-1-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (2-ethoxy-1-naphthyl) -1- Ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (3-ethoxy-1-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-ethoxy-1-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2 , 2-trifluoro-1- (5-ethoxy-1-naphthyl) -1-ethyl] -3-oxopyrazolidine, ( S) -1- [2,2,2-trifluoro-1- (6-ethoxy-1-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2, 2-trif
Fluoro-1- (7-ethoxy-1-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (8-ethoxy-1) -Naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (2-n-propoxy-1-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (3-n-propoxy-1-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-n-propoxy-1-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2 , 2,2-Trifluoro-1- (5-n-propoxy-1-naphthyl) -1-ethyl] -3-oxopyr Lysine, (S) -1- [2,2,2-trifluoro-1- (6-n-propoxy-1-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (7-n-propoxy-1-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-tri Fluoro-1- (8-n-propoxy-1-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (2-iso -Propoxy-1-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (3-iso-propoxy-1-naphthyl)- 1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4 iso-propoxy-1-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (5-iso-propoxy-1-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (6-iso-propoxy-1-naphthyl) -1-ethyl] -3- Oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (7-iso-propoxy-1-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (8-iso-propoxy-1-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2, 2-trifluoro-1- (2-n-butoxy-1-naphthyl) -1-ethyl] -3 -Oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (3-n-butoxy-1-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S ) -1- [2,2,2-trifluoro-1- (4-n-butoxy-1-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2 , 2-trifluoro-1- (5-n-butoxy-1-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (6-n-butoxy-1-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (7-n-butoxy-1) -Naphtyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (8-n- Toxi-1-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (2-iso-butoxy-1-naphthyl) -1 -Ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (3-iso-butoxy-1-naphthyl) -1-ethyl] -3-oxopyra Zolidine, (S) -1- [2,2,2-trifluoro-1- (4-iso-butoxy-1-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1 -[2,2,2-trifluoro-1- (5-iso-butoxy-1-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2- Trifluoro-1- (6-iso-butoxy-1-naphthyl) -1-ethyl] -3-oxopyrazo Gin, (S) -1- [2,2,2-trifluoro-1- (7-iso-butoxy-1-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (8-iso-butoxy-1-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-tri Fluoro-1- (2-tert-butoxy-1-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (3-tert -Butoxy-1-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-tert-butoxy-1-naphthyl)- 1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (5-tert-butoxy-1-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (6-tert-butoxy-1) -Naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (7-tert-butoxy-1-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (8-tert-butoxy-1-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (2-n-pentoxy-1-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2 , 2,2-trifluoro-1- (4-n-pentoxy-1-naphthyl) -1-ethyl] 3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (6-n-pentoxy-1-naphthyl) -1-ethyl] -3-oxopyrazolidine, ( S) -1- [2,2,2-trifluoro-1- (8-n-pentoxy-1-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2, 2,2-trifluoro-1- (2-n-hexyloxy-1-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro- 1- (4-n-hexyloxy-1-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (6-n- (Hexyloxy-1-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-to Fluoro-1- (8-n-hexyloxy-1-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (2- n-heptyloxy-1-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-n-heptyloxy-1- Naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (6-n-heptyloxy-1-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (8-n-heptyloxy-1-naphthyl) -1-ethyl] -3-oxopyrazolidine , (S) -1- [2,2,2-trifluoro-1- (2-n-octyloxy-1-na Butyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-n-octyloxy-1-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (6-n-octyloxy-1-naphthyl) -1-ethyl] -3-oxopyrazolidine (S) -1- [2,2,2-trifluoro-1- (8-n-octyloxy-1-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (2-n-nonyloxy-1-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-tri Fluoro-1- (4-n-nonyloxy-1-naphthyl) -1-ethyl] -3-oxopyrazolidine, ( ) -1- [2,2,2-trifluoro-1- (6-n-nonyloxy-1-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2 , 2-trifluoro-1- (8-n-nonyloxy-1-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (2-n-decyloxy-1-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-n-decyloxy-1) -Naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (6-n-decyloxy-1-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (8-n-dec Oxy-1-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (2-fluoro-1-naphthyl) -1-ethyl ] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (3-fluoro-1-naphthyl) -1-ethyl] -3-oxopyrazolidine, ( S) -1- [2,2,2-trifluoro-1- (4-fluoro-1-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2, 2-trifluoro-1- (5-fluoro-1-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (6- Fluoro-1-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro Oro-1- (7-fluoro-1-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (8-fluoro-1) -Naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (2-chloro-1-naphthyl) -1-ethyl] -3 -Oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (3-chloro-1-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S)- 1- [2,2,2-trifluoro-1- (4-chloro-1-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-tri Fluoro-1- (5-chloro-1-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2 Trifluoro-1- (6-chloro-1-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (7-chloro- 1-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (8-chloro-1-naphthyl) -1-ethyl]- 3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (2-bromo-1-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (3-bromo-1-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2- Trifluoro-1- (4-bromo-1-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2, , 2-trifluoro-1- (5-bromo-1-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (6 -Bromo-1-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (7-bromo-1-naphthyl) -1- Ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (8-bromo-1-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (2-cyano-1-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2 , 2-trifluoro-1- (3-cyano-1-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [ 2,2,2-trifluoro-1- (4-cyano-1-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1 -(5-cyano-1-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trif
Fluoro-1- (6-cyano-1-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (7-cyano-1) -Naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (8-cyano-1-naphthyl) -1-ethyl] -3 -Oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (2-nitro-1-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S)- 1- [2,2,2-trifluoro-1- (3-nitro-1-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-tri Fluoro-1- (4-nitro-1-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2- Lifluoro-1- (5-nitro-1-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (6-nitro-1) -Naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (7-nitro-1-naphthyl) -1-ethyl] -3 -Oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (8-nitro-1-naphthyl) -1-ethyl] -3-oxopyrazolidine, and the like. it can.

本発明の、前記一般式(1)で表される光学活性3−オキソピラゾリジン誘導体として、Rが置換基を有しても良い2−ナフチル基であるものとしては、具体的には例えば、(S)−1−[2,2,2−トリフルオロ−1−(2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−メチル−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−メチル−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−メチル−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−メチル−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−メチル−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−メチル−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−メチル−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−エチル−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−エチル−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−エチル−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−エチル−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−エチル−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−エチル−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−エチル−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−n−プロピル−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−n−プロピル−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−n−プロピル−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−プロピル−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−n−プロピル−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−プロピル−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−n−プロピル−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−プロピル−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−iso−プロピル−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−iso−プロピル−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−iso−プロピル−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−iso−プロピル−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−iso−プロピル−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−iso−プロピル−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−iso−プロピル−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−n−ブチル−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−n−ブチル−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−ブチル−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−n−ブチル−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−ブチル−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−n−ブチル−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−ブチル−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−iso−ブチル−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−iso−ブチル−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−iso−ブチル−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−iso−ブチル−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−iso−ブチル−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−iso−ブチル−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−iso−ブチル−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−iso−ブチル−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−tert−ブチル−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−tert−ブチル−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−tert−ブチル−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−tert−ブチル−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−tert−ブチル−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−tert−ブチル−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−tert−ブチル−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−tert−ブチル−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−n−ペンチル−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−ペンチル−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−ペンチル−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−ペンチル−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−n−ヘキシル−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−ヘキシル−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−ヘキシル−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−ヘキシル−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−n−ヘプチル−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−ヘプチル−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−ヘプチル−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−ヘプチル−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−n−オクチル−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−オクチル−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−オクチル−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−オクチル−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−n−ノニル−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−ノニル−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−ノニル−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−ノニル−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−n−デシル−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−デシル−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−デシル−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−デシル−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−メトキシ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−メトキシ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−メトキシ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−メトキシ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−メトキシ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−メトキシ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−メトキシ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−エトキシ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−エトキシ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[
2,2,2−トリフルオロ−1−(4−エトキシ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−エトキシ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−エトキシ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−エトキシ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−エトキシ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−n−プロポキ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−n−プロポキ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−プロポキ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−n−プロポキ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−プロポキ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−n−プロポキ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−プロポキ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−iso−プロポキ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−iso−プロポキ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−iso−プロポキ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−iso−プロポキ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−iso−プロポキ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−iso−プロポキ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−iso−プロポキ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−n−ブトキシ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−n−ブトキシ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−ブトキシ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−n−ブトキシ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−ブトキシ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−n−ブトキシ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−ブトキシ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−iso−ブトキシ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−iso−ブトキシ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−iso−ブトキシ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−iso−ブトキシ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−iso−ブトキシ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−iso−ブトキシ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−iso−ブトキシ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−tert−ブトキシ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−tert−ブトキシ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−tert−ブトキシ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−tert−ブトキシ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−tert−ブトキシ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−tert−ブトキシ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−tert−ブトキシ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−n−ペントキシ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−ペントキシ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−ペントキシ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−ペントキシ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−n−ヘキシルオキシ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−ヘキシルオキシ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−ヘキシルオキシ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−ヘキシルオキシ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−n−ヘプチルオキシ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−ヘプチルオキシ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−ヘプチルオキシ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−ヘプチルオキシ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−n−オクチルオキシ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−オクチルオキシ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−オクチルオキシ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−オクチルオキシ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−n−ノニルオキシ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−ノニルオキシ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−ノニルオキシ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−ノニルオキシ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−n−デシルオキシ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−デシルオキシ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−デシルオキシ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−デシルオキシ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−フルオロ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−フルオロ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−フルオロ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−フルオロ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−フルオロ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−フルオロ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−フルオロ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−クロロ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−クロロ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−クロロ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−クロロ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−クロロ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−クロロ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−クロロ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−ブロモ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−ブロモ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−ブロモ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−ブロモ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−ブロモ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−ブロモ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−ブロモ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−シアノ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオ
ロ−1−(3−シアノ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−シアノ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−シアノ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−シアノ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−シアノ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−シアノ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−ニトロ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−ニトロ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−ニトロ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−ニトロ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−ニトロ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−ニトロ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−ニトロ−2−ナフチル)−1−エチル]−3−オキソピラゾリジン等を挙げることができる。
As the optically active 3-oxopyrazolidine derivative represented by the general formula (1) of the present invention, R 3 Specific examples of the 2-naphthyl group that may have a substituent include (S) -1- [2,2,2-trifluoro-1- (2-naphthyl) -1 -Ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (1-methyl-2-naphthyl) -1-ethyl] -3-oxopyrazolidine (S) -1- [2,2,2-trifluoro-1- (3-methyl-2-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2, 2,2-trifluoro-1- (4-methyl-2-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- ( 5-methyl-2-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- 6-methyl-2-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (7-methyl-2-naphthyl) -1 -Ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (8-methyl-2-naphthyl) -1-ethyl] -3-oxopyrazolidine (S) -1- [2,2,2-trifluoro-1- (1-ethyl-2-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2, 2,2-trifluoro-1- (3-ethyl-2-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- ( 4-ethyl-2-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro 1- (5-ethyl-2-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (6-ethyl-2-naphthyl) ) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (7-ethyl-2-naphthyl) -1-ethyl] -3-oxo Pyrazolidine, (S) -1- [2,2,2-trifluoro-1- (8-ethyl-2-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (1-n-propyl-2-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-tri Fluoro-1- (2-n-propyl-2-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2, 2-trifluoro-1- (3-n-propyl-2-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- ( 4-n-propyl-2-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (5-n-propyl-2-) Naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (6-n-propyl-2-naphthyl) -1-ethyl]- 3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (7-n-propyl-2-naphthyl) -1-ethyl] -3-oxopyrazolidine, ( S) -1- [2,2,2-trifluoro-1- (8-n-propyl-2-naphthyl) -1-ethyl] -3- Xopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (1-iso-propyl-2-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (3-iso-propyl-2-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-tri Fluoro-1- (4-iso-propyl-2-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (5-iso -Propyl-2-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (6-iso-propyl-2-naphthyl)- 1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro -1- (7-iso-propyl-2-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (8-iso- Propyl-2-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (1-n-butyl-2-naphthyl) -1 -Ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (3-n-butyl-2-naphthyl) -1-ethyl] -3-oxopyra Zolidine, (S) -1- [2,2,2-trifluoro-1- (4-n-butyl-2-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1 -[2,2,2-trifluoro-1- (5-n-butyl-2-naphthyl) -1-ethyl] -3-oxopyrazolid (S) -1- [2,2,2-trifluoro-1- (6-n-butyl-2-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (7-n-butyl-2-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-tri Fluoro-1- (8-n-butyl-2-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (1-iso -Butyl-2-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (2-iso-butyl-2-naphthyl)- 1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (3-iso-butyl-2-naphth L) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-iso-butyl-2-naphthyl) -1-ethyl]- 3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (5-iso-butyl-2-naphthyl) -1-ethyl] -3-oxopyrazolidine, ( S) -1- [2,2,2-trifluoro-1- (6-iso-butyl-2-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2, 2,2-trifluoro-1- (7-iso-butyl-2-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1 -(8-Iso-butyl-2-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2 2-trifluoro-1- (1-tert-butyl-2-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- ( 2-tert-butyl-2-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (3-tert-butyl-2- Naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-tert-butyl-2-naphthyl) -1-ethyl]- 3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (5-tert-butyl-2-naphthyl) -1-ethyl] -3-oxopyrazolidine, ( S) -1- [2,2,2-trifluoro-1- (6-tert-butyl-2-naphthy) L) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (7-tert-butyl-2-naphthyl) -1-ethyl]- 3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (8-tert-butyl-2-naphthyl) -1-ethyl] -3-oxopyrazolidine, ( S) -1- [2,2,2-trifluoro-1- (1-n-pentyl-2-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2, 2,2-trifluoro-1- (4-n-pentyl-2-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1 -(6-n-pentyl-2-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2 Trifluoro-1- (8-n-pentyl-2-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (1- n-hexyl-2-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-n-hexyl-2-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (6-n-hexyl-2-naphthyl) -1-ethyl] -3- Oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (8-n-hexyl-2-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (1-n-heptyl-2-naphthyl) -1-ethyl] -3-o Sopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-n-heptyl-2-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (6-n-heptyl-2-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-tri Fluoro-1- (8-n-heptyl-2-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (1-n -Octyl-2-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-n-octyl-2-naphthyl)- 1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (6-n-octyl) Ru-2-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (8-n-octyl-2-naphthyl) -1 -Ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (1-n-nonyl-2-naphthyl) -1-ethyl] -3-oxopyra Zolidine, (S) -1- [2,2,2-trifluoro-1- (4-n-nonyl-2-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1 -[2,2,2-trifluoro-1- (6-n-nonyl-2-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2- Trifluoro-1- (8-n-nonyl-2-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2- Lifluoro-1- (1-n-decyl-2-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-n -Decyl-2-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (6-n-decyl-2-naphthyl)- 1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (8-n-decyl-2-naphthyl) -1-ethyl] -3-oxo Pyrazolidine, (S) -1- [2,2,2-trifluoro-1- (1-methoxy-2-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (3-methoxy-2-naphthyl) -1-ethyl] -3-oxopyrazolidine, S) -1- [2,2,2-trifluoro-1- (4-methoxy-2-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2, 2-trifluoro-1- (5-methoxy-2-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (6- Methoxy-2-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (7-methoxy-2-naphthyl) -1-ethyl ] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (8-methoxy-2-naphthyl) -1-ethyl] -3-oxopyrazolidine, ( S) -1- [2,2,2-trifluoro-1- (1-ethoxy-2-naphthyl) -1-ethyl] -3-oxy Sopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (3-ethoxy-2-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [
2,2,2-trifluoro-1- (4-ethoxy-2-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1 -(5-Ethoxy-2-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (6-ethoxy-2-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (7-ethoxy-2-naphthyl) -1-ethyl] -3-oxopyra Zolidine, (S) -1- [2,2,2-trifluoro-1- (8-ethoxy-2-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [ 2,2,2-trifluoro-1- (1-n-propoxy-2-naphthyl) -1-ethyl] -3-oxopyrazo Gin, (S) -1- [2,2,2-trifluoro-1- (3-n-propoxy-2-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-n-propoxy-2-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-tri Fluoro-1- (5-n-propoxy-2-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (6-n -Propoxy-2-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (7-n-propoxy-2-naphthyl)- 1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (8-n-propoxy-2- Butyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (1-iso-propoxy-2-naphthyl) -1-ethyl]- 3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (3-iso-propoxy-2-naphthyl) -1-ethyl] -3-oxopyrazolidine, ( S) -1- [2,2,2-trifluoro-1- (4-iso-propoxy-2-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2, 2,2-trifluoro-1- (5-iso-propoxy-2-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1 -(6-iso-propoxy-2-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S)- 1- [2,2,2-trifluoro-1- (7-iso-propoxy-2-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2 -Trifluoro-1- (8-iso-propoxy-2-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (1 -N-butoxy-2-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (3-n-butoxy-2-naphthyl) ) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-n-butoxy-2-naphthyl) -1-ethyl] -3 -Oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (5-n-butoxy-2-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (6-n-butoxy-2-naphthyl) -1-ethyl] -3- Oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (7-n-butoxy-2-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (8-n-butoxy-2-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2, 2-trifluoro-1- (1-iso-butoxy-2-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- ( 3-iso-butoxy-2-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2- Lifluoro-1- (4-iso-butoxy-2-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (5-iso -Butoxy-2-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (6-iso-butoxy-2-naphthyl)- 1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (7-iso-butoxy-2-naphthyl) -1-ethyl] -3-oxo Pyrazolidine, (S) -1- [2,2,2-trifluoro-1- (8-iso-butoxy-2-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S)- 1- [2,2,2-trifluoro-1- (1-tert-butoxy-2-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (3-tert-butoxy-2-naphthyl) -1-ethyl] -3- Oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-tert-butoxy-2-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (5-tert-butoxy-2-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2, 2-trifluoro-1- (6-tert-butoxy-2-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- ( 7-tert-butoxy-2-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) 1- [2,2,2-trifluoro-1- (8-tert-butoxy-2-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2 -Trifluoro-1- (1-n-pentoxy-2-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4 -N-pentoxy-2-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (6-n-pentoxy-2-naphthyl) ) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (8-n-pentoxy-2-naphthyl) -1-ethyl] -3 -Oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (1-n-hexyloxy) 2-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-n-hexyloxy-2-naphthyl) -1- Ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (6-n-hexyloxy-2-naphthyl) -1-ethyl] -3-oxopyra Zolidine, (S) -1- [2,2,2-trifluoro-1- (8-n-hexyloxy-2-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S)- 1- [2,2,2-trifluoro-1- (1-n-heptyloxy-2-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2, 2-trifluoro-1- (4-n-heptyloxy-2-naphthyl) -1-ethyl] -3-oxopyrazo Lysine, (S) -1- [2,2,2-trifluoro-1- (6-n-heptyloxy-2-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1 -[2,2,2-trifluoro-1- (8-n-heptyloxy-2-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2 -Trifluoro-1- (1-n-octyloxy-2-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- ( 4-n-octyloxy-2-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (6-n-octyloxy-) 2-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro 1- (8-n-octyloxy-2-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (1-n- Nonyloxy-2-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-n-nonyloxy-2-naphthyl) -1 -Ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (6-n-nonyloxy-2-naphthyl) -1-ethyl] -3-oxopyra Zolidine, (S) -1- [2,2,2-trifluoro-1- (8-n-nonyloxy-2-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1 -[2,2,2-trifluoro-1- (1-n-decyloxy-2-naphthyl) -1-eth ] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-n-decyloxy-2-naphthyl) -1-ethyl] -3-oxopyrazolidine (S) -1- [2,2,2-trifluoro-1- (6-n-decyloxy-2-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [ 2,2,2-trifluoro-1- (8-n-decyloxy-2-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro -1- (1-fluoro-2-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (3-fluoro-2- Naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-Fluoro-2-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (5-fluoro-2-naphthyl)- 1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (6-fluoro-2-naphthyl) -1-ethyl] -3-oxopyrazo Lysine, (S) -1- [2,2,2-trifluoro-1- (7-fluoro-2-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2 , 2,2-trifluoro-1- (8-fluoro-2-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (1-chloro-2-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-to Fluoro-1- (3-chloro-2-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-chloro-2) -Naphtyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (5-chloro-2-naphthyl) -1-ethyl] -3 -Oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (6-chloro-2-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S)- 1- [2,2,2-trifluoro-1- (7-chloro-2-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-tri Fluoro-1- (8-chloro-2-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2, -Trifluoro-1- (1-bromo-2-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (3-bromo -2-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-bromo-2-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (5-bromo-2-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S ) -1- [2,2,2-trifluoro-1- (6-bromo-2-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2 -Trifluoro-1- (7-bromo-2-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2, 2,2-trifluoro-1- (8-bromo-2-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- ( 1-cyano-2-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro
B-1- (3-Cyano-2-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-cyano-2) -Naphtyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (5-cyano-2-naphthyl) -1-ethyl] -3 -Oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (6-cyano-2-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S)- 1- [2,2,2-trifluoro-1- (7-cyano-2-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-tri Fluoro-1- (8-cyano-2-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-tri Fluoro-1- (1-nitro-2-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (3-nitro-2) -Naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-nitro-2-naphthyl) -1-ethyl] -3 -Oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (5-nitro-2-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S)- 1- [2,2,2-trifluoro-1- (6-nitro-2-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2-tri Fluoro-1- (7-nitro-2-naphthyl) -1-ethyl] -3-oxopyrazolidine, (S) -1- [2,2,2 And tri-fluoro-1- (8-nitro-2-naphthyl) -1-ethyl] -3-oxo-pyrazolidinedione like.

本発明の、前記一般式(1)で表される光学活性3−オキソピラゾリジン誘導体として、Rが置換基を有しても良いアリールエチレニル基であるものとしては、具体的には例えば、(S)−1−[1−(トリフルオロメチル)−3−フェニル−2−プロペン]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(2−メチルフェニル)−2−プロペン)]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(3−メチルフェニル)−2−プロペン)]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(4−メチルフェニル)−2−プロペン)]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(2−エチルフェニル)−2−プロペン)]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(3−エチルフェニル)−2−プロペン)]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(4−エチルフェニル)−2−プロペン)]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(2−n−プロピルフェニル)−2−プロペン)]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(3−n−プロピルフェニル)−2−プロペン)]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(4−n−プロピルフェニル)−2−プロペン)]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(2−iso−プロピルフェニル)−2−プロペン)]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(3−iso−プロピルフェニル)−2−プロペン)]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(4−iso−プロピルフェニル)−2−プロペン)]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(2−n−ブチルフェニル)−2−プロペン)]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(3−n−ブチルフェニル)−2−プロペン)]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(4−n−ブチルフェニル)−2−プロペン)]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(2−sec−ブチルフェニル)−2−プロペン)]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(3−sec−ブチルフェニル)−2−プロペン)]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(4−sec−ブチルフェニル)−2−プロペン)]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(2−tert−ブチルフェニル)−2−プロペン)]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(3−tert−ブチルフェニル)−2−プロペン)]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(4−tert−ブチルフェニル)−2−プロペン)]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(2−メトキシフェニル)−2−プロペン)]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(3−メトキシフェニル)−2−プロペン)]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(4−メトキシフェニル)−2−プロペン)]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(2−エトキシフェニル)−2−プロペン)]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(3−エトキシフェニル)−2−プロペン)]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(4−エトキシフェニル)−2−プロペン)]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(2−n−プロポキシフェニル)−2−プロペン)]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(3−n−プロポキシフェニル)−2−プロペン)]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(4−n−プロポキシフェニル)−2−プロペン)]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(2−iso−プロポキシフェニル)−2−プロペン)]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(3−iso−プロポキシフェニル)−2−プロペン)]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(4−iso−プロポキシフェニル)−2−プロペン)]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(2−n−ブトキシフェニル)−2−プロペン)]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(3−n−ブトキシフェニル)−2−プロペン)]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(4−n−ブトキシフェニル)−2−プロペン)]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(2−sec−ブトキシフェニル)−2−プロペン)]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(3−sec−ブトキシフェニル)−2−プロペン)]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(4−sec−ブトキシフェニル)−2−プロペン)]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(2−tert−ブトキシフェニル)−2−プロペン)]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(3−tert−ブトキシフェニル)−2−プロペン)]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(4−tert−ブトキシフェニル)−2−プロペン)]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(2−フルオロフェニル)−2−プロペン)]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(3−フルオロフェニル)−2−プロペン)]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(4−フルオロフェニル)−2−プロペン)]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(2−クロロフェニル)−2−プロペン)]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(3−クロロフェニル)−2−プロペン)]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(4−クロロフェニル)−2−プロペン)]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(2−ブロモフェニル)−2−プロペン)]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(3−ブロモフェニル)−2−プロペン)]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(4−ブロモフェニル)−2−プロペン)]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(2−シアノフェニル)−2−プロペン)]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(3−シアノフェニル)−2−プロペン)]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(4−シアノフェニル)−2−プロペン)]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(2−ニトロフェニル)−2−プロペン)]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(3−ニトロフェニル)−2−プロペン)]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(4−ニトロフェニル)−2−プロペン)]−3−オキソピラゾリジン等を挙げることができる。 As the optically active 3-oxopyrazolidine derivative represented by the general formula (1) of the present invention, R 3 may be an arylethylenyl group which may have a substituent. Specifically, For example, (S) -1- [1- (trifluoromethyl) -3-phenyl-2-propene] -3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (2-Methylphenyl) -2-propene)]-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (3-methylphenyl) -2-propene)]- 3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (4-methylphenyl) -2-propene)]-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (2-ethylphenyl)- 2-propene)]-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (3-ethylphenyl) -2-propene)]-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (4-ethylphenyl) -2-propene)]-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) ) -3- (2-n-propylphenyl) -2-propene)]-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (3-n-propylphenyl) ) -2-propene)]-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (4-n-propylphenyl) -2-propene)]-3-oxo Pyrazolidine, (S) -1- [1- (trifluoromethyl) -3- 2-iso-propylphenyl) -2-propene)]-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (3-iso-propylphenyl) -2-propene )]-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (4-iso-propylphenyl) -2-propene)]-3-oxopyrazolidine, S) -1- [1- (trifluoromethyl) -3- (2-n-butylphenyl) -2-propene)]-3-oxopyrazolidine, (S) -1- [1- (trifluoro Methyl) -3- (3-n-butylphenyl) -2-propene)]-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (4-n-butyl) Phenyl) -2-propene)]-3-oxopyrazolidine (S) -1- [1- (trifluoromethyl) -3- (2-sec-butylphenyl) -2-propene)]-3-oxopyrazolidine, (S) -1- [1- (tri Fluoromethyl) -3- (3-sec-butylphenyl) -2-propene)]-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (4-sec- Butylphenyl) -2-propene)]-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (2-tert-butylphenyl) -2-propene)]-3 -Oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (3-tert-butylphenyl) -2-propene)]-3-oxopyrazolidine, (S) -1 -[1- (trifluoromethyl) -3- (4-tert- Butylphenyl) -2-propene)]-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (2-methoxyphenyl) -2-propene)]-3-oxo Pyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (3-methoxyphenyl) -2-propene)]-3-oxopyrazolidine, (S) -1- [1- (Trifluoromethyl) -3- (4-methoxyphenyl) -2-propene)]-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (2-ethoxyphenyl) ) -2-propene)]-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (3-ethoxyphenyl) -2-propene)]-3-oxopyrazo Lysine, (S) -1- [1- (trifluoromethyl) ) -3- (4-Ethoxyphenyl) -2-propene)]-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (2-n-propoxyphenyl)- 2-propene)]-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (3-n-propoxyphenyl) -2-propene)]-3-oxopyrazo Lysine, (S) -1- [1- (trifluoromethyl) -3- (4-n-propoxyphenyl) -2-propene)]-3-oxopyrazolidine, (S) -1- [1- (Trifluoromethyl) -3- (2-iso-propoxyphenyl) -2-propene)]-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (3- iso-propoxyphenyl) -2-propene)]-3- Xopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (4-iso-propoxyphenyl) -2-propene)]-3-oxopyrazolidine, (S) -1- [1- (Trifluoromethyl) -3- (2-n-butoxyphenyl) -2-propene)]-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (3- n-butoxyphenyl) -2-propene)]-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (4-n-butoxyphenyl) -2-propene)] -3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (2-sec-butoxyphenyl) -2-propene)]-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- ( 3-sec-butoxyphenyl) -2-propene)]-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (4-sec-butoxyphenyl) -2-propene )]-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (2-tert-butoxyphenyl) -2-propene)]-3-oxopyrazolidine, S) -1- [1- (trifluoromethyl) -3- (3-tert-butoxyphenyl) -2-propene)]-3-oxopyrazolidine, (S) -1- [1- (trifluoro Methyl) -3- (4-tert-butoxyphenyl) -2-propene)]-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (2-fluorophenyl) -2-propene)]-3-oki Pyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (3-fluorophenyl) -2-propene)]-3-oxopyrazolidine, (S) -1- [1- (tri Fluoromethyl) -3- (4-fluorophenyl) -2-propene)]-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (2-chlorophenyl) -2 -Propene)]-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (3-chlorophenyl) -2-propene)]-3-oxopyrazolidine, (S ) -1- [1- (trifluoromethyl) -3- (4-chlorophenyl) -2-propene)]-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3 -(2-bromophenyl) -2-propene)] 3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (3-bromophenyl) -2-propene)]-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (4-bromophenyl) -2-propene)]-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (2 -Cyanophenyl) -2-propene)]-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (3-cyanophenyl) -2-propene)]-3- Oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (4-cyanophenyl) -2-propene)]-3-oxopyrazolidine, (S) -1- [1 -(Trifluoromethyl) -3- (2-nitrophenyl) -2-propene )]-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (3-nitrophenyl) -2-propene)]-3-oxopyrazolidine, (S) Examples include -1- [1- (trifluoromethyl) -3- (4-nitrophenyl) -2-propene)]-3-oxopyrazolidine.

本発明の、前記一般式(1)で表される光学活性3−オキソピラゾリジン誘導体として、Rが置換基を有しても良いアリールアルキル基であるものとしては、具体的には例えば、(S)−1−[1−(トリフルオロメチル)−2−フェニルエチル]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−フェニルプロピル]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−4−フェニルブチル]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−5−フェニルペンチル]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−6−フェニルヘキシル]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−2−(2−メチルフェニル)エチル]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−2−(3−メチルフェニル)エチル]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−2−(4−メチルフェニル)エチル]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(2−メチルフェニル)プロピル]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(3−メチルフェニル)プロピル]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(4−メチルフェニル)プロピル]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−4−(2−メチルフェニル)ブチル]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−4−(3−メチルフェニル)ブチル]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−4−(4−メチルフェニル)ブチル]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−5−(2−メチルフェニル)ペンチル]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−5−(3−メチルフェニル)ペンチル]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−5−(4−メチルフェニル)ペンチル]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−2−(2−エチルフェニル)エチル]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−2−(3−エチルフェニル)エチル]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−2−(4−エチルフェニル)エチル]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(2−エチルフェニル)プロピル]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(3−エチルフェニル)プロピル]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(4−エチルフェニル)プロピル]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−4−(2−エチルフェニル)ブチル]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−4−(3−エチルフェニル)ブチル]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−4−(4−エチルフェニル)ブチル]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−5−(2−エチルフェニル)ペンチル]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−5−(3−エチルフェニル)ペンチル]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−5−(4−エチルフェニル)ペンチル]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−2−(2−メトキシフェニル)エチル]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−2−(3−メトキシフェニル)エチル]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−2−(4−メトキシフェニル)エチル]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(2−メトキシフェニル)プロピル]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(3−メトキシフェニル)プロピル]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(4−メトキシフェニル)プロピル]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−4−(2−メトキシフェニル)ブチル]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−4−(3−メトキシフェニル)ブチル]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−4−(4−メトキシフェニル)ブチル]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−5−(2−メトキシフェニル)ペンチル]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−5−(3−メトキシフェニル)ペンチル]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−5−(4−メトキシフェニル)ペンチル]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−2−(2−エトキシフェニル)エチル]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−2−(3−エトキシフェニル)エチル]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−2−(4−エトキシフェニル)エチル]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(2−エトキシフェニル)プロピル]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(3−エトキシフェニル)プロピル]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(4−エトキシフェニル)プロピル]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−4−(2−エトキシフェニル)ブチル]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−4−(3−エトキシフェニル)ブチル]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−4−(4−エトキシフェニル)ブチル]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−5−(2−エトキシフェニル)ペンチル]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−5−(3−エトキシフェニル)ペンチル]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−5−(4−エトキシフェニル)ペンチル]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−2−(2−フルオロフェニル)エチル]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−2−(3−フルオロフェニル)エチル]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−2−(4−フルオロフェニル)エチル]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(2−フルオロフェニル)プロピル]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(3−フルオロフェニル)プロピル]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(4−フルオロフェニル)プロピル]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−4−(2−フルオロフェニル)ブチル]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−4−(3−フルオロフェニル)ブチル]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−4−(4−フルオロフェニル)ブチル]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−5−(2−フルオロフェニル)ペンチル]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−5−(3−フルオロフェニル)ペンチル]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−5−(4−フルオロフェニル)ペンチル]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−2−(2−クロロフェニル)エチル]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−2−(3−クロロフェニル)エチル]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−2−(4−クロロフェニル)エチル]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(2−クロロフェニル)プロピル]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(3−クロロフェニル)プロピル]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(4−クロロフェニル)プロピル]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−4−(2−クロロフェニル)ブチル]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−4−(3−クロロフェニル)ブチル]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−4−(4−クロロフェニル)ブチル]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−5−(2−クロロフェニル)ペンチル]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−5−(3−クロロフェニル)ペンチル]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−5−(4−クロロフェニル)ペンチル]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−2−(2−ブロモフェニル)エチル]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−2−(3−ブロモフェニル)エチル]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−2−(4−ブロモフェニル)エチル]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(2−ブロモフェニル)プロピル]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(3−ブロモフェニル)プロピル]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(4−ブロモフェニル)プロピル]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−4−(2−ブロモフェニル)ブチル]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−4−(3−ブロモフェニル)ブチル]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−4−(4−ブロモフェニル)ブチル]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−5−(2−ブロモフェニル)ペンチル]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−5−(3−ブロモフェニル)ペンチル]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−5−(4−ブロモフェニル)ペンチル]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−2−(2−シアノフェニル)エチル]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−2−(3−シアノフェニル)エチル]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−2−(4−シアノフェニル)エチル]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(2−シアノフェニル)プロピル]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(3−シアノフェニル)プロピル]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(4−シアノフェニル)プロピル]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−4−(2−シアノフェニル)ブチル]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−4−(3−シアノフェニル)ブチル]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−4−(4−シアノフェニル)ブチル
]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−5−(2−シアノフェニル)ペンチル]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−5−(3−シアノフェニル)ペンチル]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−5−(4−シアノフェニル)ペンチル]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−2−(2−ニトロフェニル)エチル]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−2−(3−ニトロフェニル)エチル]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−2−(4−ニトロフェニル)エチル]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(2−ニトロフェニル)プロピル]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(3−ニトロフェニル)プロピル]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(4−ニトロフェニル)プロピル]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−4−(2−ニトロフェニル)ブチル]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−4−(3−ニトロフェニル)ブチル]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−4−(4−ニトロフェニル)ブチル]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−5−(2−ニトロフェニル)ブチル]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−5−(3−ニトロフェニル)ブチル]−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−5−(4−ニトロフェニル)ブチル]−3−オキソピラゾリジン等を挙げることができる。
Specific examples of the optically active 3-oxopyrazolidine derivative represented by the general formula (1) of the present invention in which R 3 is an arylalkyl group which may have a substituent include (S) -1- [1- (trifluoromethyl) -2-phenylethyl] -3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3-phenylpropyl]- 3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -4-phenylbutyl] -3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl)- 5-phenylpentyl] -3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -6-phenylhexyl] -3-oxopyrazolidine, (S) -1- [1- (Trifluoromethyl) -2- (2-methyl Phenyl) ethyl] -3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -2- (3-methylphenyl) ethyl] -3-oxopyrazolidine, (S) -1 -[1- (trifluoromethyl) -2- (4-methylphenyl) ethyl] -3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (2-methylphenyl) ) Propyl] -3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (3-methylphenyl) propyl] -3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (4-methylphenyl) propyl] -3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -4- (2-methylphenyl) Butyl] -3-oxopyrazolidine, (S -1- [1- (trifluoromethyl) -4- (3-methylphenyl) butyl] -3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -4- (4- Methylphenyl) butyl] -3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -5- (2-methylphenyl) pentyl] -3-oxopyrazolidine, (S)- 1- [1- (trifluoromethyl) -5- (3-methylphenyl) pentyl] -3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -5- (4-methyl) Phenyl) pentyl] -3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -2- (2-ethylphenyl) ethyl] -3-oxopyrazolidine, (S) -1 -[1- (trifluoromethyl) -2- (3- Tilphenyl) ethyl] -3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -2- (4-ethylphenyl) ethyl] -3-oxopyrazolidine, (S) -1 -[1- (trifluoromethyl) -3- (2-ethylphenyl) propyl] -3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (3-ethylphenyl) ) Propyl] -3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (4-ethylphenyl) propyl] -3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -4- (2-ethylphenyl) butyl] -3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -4- (3-ethylphenyl) Butyl] -3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -4- (4-ethylphenyl) butyl] -3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -5 (2-ethylphenyl) pentyl] -3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -5- (3-ethylphenyl) pentyl] -3-oxopyrazolidine, ( S) -1- [1- (trifluoromethyl) -5- (4-ethylphenyl) pentyl] -3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -2- ( 2-methoxyphenyl) ethyl] -3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -2- (3-methoxyphenyl) ethyl] -3-oxopyrazolidine, (S ) -1- [1- (trifluoromethyl) -2 (4-methoxyphenyl) ethyl] -3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (2-methoxyphenyl) propyl] -3-oxopyrazolidine, ( S) -1- [1- (trifluoromethyl) -3- (3-methoxyphenyl) propyl] -3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- ( 4-methoxyphenyl) propyl] -3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -4- (2-methoxyphenyl) butyl] -3-oxopyrazolidine, (S ) -1- [1- (trifluoromethyl) -4- (3-methoxyphenyl) butyl] -3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -4- (4) -Methoxyphenyl) butyl]- -Oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -5- (2-methoxyphenyl) pentyl] -3-oxopyrazolidine, (S) -1- [1- (tri Fluoromethyl) -5- (3-methoxyphenyl) pentyl] -3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -5- (4-methoxyphenyl) pentyl] -3- Oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -2- (2-ethoxyphenyl) ethyl] -3-oxopyrazolidine, (S) -1- [1- (trifluoro) Methyl) -2- (3-ethoxyphenyl) ethyl] -3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -2- (4-ethoxyphenyl) ethyl] -3-oxo Pyrazolidine, (S) -1- [ 1- (trifluoromethyl) -3- (2-ethoxyphenyl) propyl] -3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (3-ethoxyphenyl) propyl ] -3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (4-ethoxyphenyl) propyl] -3-oxopyrazolidine, (S) -1- [1 -(Trifluoromethyl) -4- (2-ethoxyphenyl) butyl] -3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -4- (3-ethoxyphenyl) butyl] -3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -4- (4-ethoxyphenyl) butyl] -3-oxopyrazolidine, (S) -1- [1- (Trifluoromethyl) -5- (2 Ethoxyphenyl) pentyl] -3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -5- (3-ethoxyphenyl) pentyl] -3-oxopyrazolidine, (S)- 1- [1- (trifluoromethyl) -5- (4-ethoxyphenyl) pentyl] -3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -2- (2-fluoro Phenyl) ethyl] -3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -2- (3-fluorophenyl) ethyl] -3-oxopyrazolidine, (S) -1 -[1- (trifluoromethyl) -2- (4-fluorophenyl) ethyl] -3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (2-fluorophenyl) ) Propyl] -3- Xopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (3-fluorophenyl) propyl] -3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl)- 3- (4-Fluorophenyl) propyl] -3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -4- (2-fluorophenyl) butyl] -3-oxopyrazolidine , (S) -1- [1- (trifluoromethyl) -4- (3-fluorophenyl) butyl] -3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -4 -(4-fluorophenyl) butyl] -3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -5- (2-fluorophenyl) pentyl] -3-oxopyrazolidine, (S) -1- [1- (Trifluoromethyl) -5- (3-fluorophenyl) pentyl] -3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -5- (4-fluorophenyl) pentyl]- 3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -2- (2-chlorophenyl) ethyl] -3-oxopyrazolidine, (S) -1- [1- (tri (Fluoromethyl) -2- (3-chlorophenyl) ethyl] -3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -2- (4-chlorophenyl) ethyl] -3-oxopyra Zolidine, (S) -1- [1- (trifluoromethyl) -3- (2-chlorophenyl) propyl] -3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl)- 3- (3-Chlorofe ) Propyl] -3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (4-chlorophenyl) propyl] -3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -4- (2-chlorophenyl) butyl] -3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -4- (3-chlorophenyl) butyl] -3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -4- (4-chlorophenyl) butyl] -3-oxopyrazolidine, (S) -1- [1- ( (Trifluoromethyl) -5- (2-chlorophenyl) pentyl] -3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -5- (3-chlorophenyl) pentyl] -3-oxo Pyrazolidine, (S) 1- [1- (trifluoromethyl) -5- (4-chlorophenyl) pentyl] -3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -2- (2-bromophenyl) ) Ethyl] -3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -2- (3-bromophenyl) ethyl] -3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -2- (4-bromophenyl) ethyl] -3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (2-bromophenyl) Propyl] -3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (3-bromophenyl) propyl] -3-oxopyrazolidine, (S) -1- [ 1- (trifluoromethyl) -3- (4-brom Mophenyl) propyl] -3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -4- (2-bromophenyl) butyl] -3-oxopyrazolidine, (S) -1 -[1- (trifluoromethyl) -4- (3-bromophenyl) butyl] -3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -4- (4-bromophenyl) ) Butyl] -3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -5- (2-bromophenyl) pentyl] -3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -5- (3-bromophenyl) pentyl] -3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -5- (4-bromophenyl) Pentyl] -3-oxopyrazolidine, S) -1- [1- (trifluoromethyl) -2- (2-cyanophenyl) ethyl] -3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -2- ( 3-cyanophenyl) ethyl] -3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -2- (4-cyanophenyl) ethyl] -3-oxopyrazolidine, (S ) -1- [1- (trifluoromethyl) -3- (2-cyanophenyl) propyl] -3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (3 -Cyanophenyl) propyl] -3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (4-cyanophenyl) propyl] -3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -4- ( -Cyanophenyl) butyl] -3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -4- (3-cyanophenyl) butyl] -3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -4- (4-cyanophenyl) butyl] -3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -5- (2- Cyanophenyl) pentyl] -3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -5- (3-cyanophenyl) pentyl] -3-oxopyrazolidine, (S)- 1- [1- (trifluoromethyl) -5- (4-cyanophenyl) pentyl] -3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -2- (2-nitro Phenyl) ethyl] -3-oxopyrazolid (S) -1- [1- (trifluoromethyl) -2- (3-nitrophenyl) ethyl] -3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl)- 2- (4-Nitrophenyl) ethyl] -3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (2-nitrophenyl) propyl] -3-oxopyrazolidine (S) -1- [1- (trifluoromethyl) -3- (3-nitrophenyl) propyl] -3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3 -(4-nitrophenyl) propyl] -3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -4- (2-nitrophenyl) butyl] -3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -4 (3-nitrophenyl) butyl] -3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -4- (4-nitrophenyl) butyl] -3-oxopyrazolidine, ( S) -1- [1- (trifluoromethyl) -5- (2-nitrophenyl) butyl] -3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -5- ( 3-nitrophenyl) butyl] -3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -5- (4-nitrophenyl) butyl] -3-oxopyrazolidine, etc. be able to.

本発明の一般式(1)で表される光学活性4,4−ジメチル−3−オキソピペラゾリジン誘導体で、Rがメチル基、エチル基、炭素数3〜10の直鎖、分岐若しくは環式のアルキル基であるものとしては、具体的には例えば、(S)−1−(1,1,1−トリフルオロ−2−プロピル)−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−(1,1,1−トリフルオロ−2−ブチル)−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−(1,1,1−トリフルオロ−2−ペンチル)−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−(1,1,1−トリフルオロ−3−メチル−2−ブチル)−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−(1,1,1−トリフルオロ−2−ヘキシル)−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−(1,1,1−トリフルオロ−3,3−ジメチル−2−ブチレン)−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−(1,1,1−トリフルオロ−2−ヘプチル)−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−(1,1,1−トリフルオロ−2−オクチル)−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−(1,1,1−トリフルオロ−3−シクロヘキシル−2−エチル)−4,4−ジメチル−3−オキソピラゾリン、(S)−1−(1,1,1−トリフルオロ−2−ノニル)−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−(1,1,1−トリフルオロ−2−デシル)−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−(1,1,1−トリフルオロ−2−ウンデシル)−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−(1,1,1−トリフルオロ−2−ドデシル)−3−オキソピラゾリジン等を挙げることができる。 An optically active 4,4-dimethyl-3-oxopiperazolidine derivative represented by the general formula (1) of the present invention, wherein R 3 is a methyl group, an ethyl group, a linear, branched or ring having 3 to 10 carbon atoms. Specific examples of the alkyl group of the formula include (S) -1- (1,1,1-trifluoro-2-propyl) -4,4-dimethyl-3-oxopyrazolidine, (S) -1- (1,1,1-trifluoro-2-butyl) -4,4-dimethyl-3-oxopyrazolidine, (S) -1- (1,1,1-trifluoro- 2-pentyl) -4,4-dimethyl-3-oxopyrazolidine, (S) -1- (1,1,1-trifluoro-3-methyl-2-butyl) -4,4-dimethyl-3 -Oxopyrazolidine, (S) -1- (1,1,1-trifluoro-2-hexyl) -4,4-dimethyl Ru-3-oxopyrazolidine, (S) -1- (1,1,1-trifluoro-3,3-dimethyl-2-butylene) -4,4-dimethyl-3-oxopyrazolidine, ( S) -1- (1,1,1-trifluoro-2-heptyl) -4,4-dimethyl-3-oxopyrazolidine, (S) -1- (1,1,1-trifluoro-2) -Octyl) -4,4-dimethyl-3-oxopyrazolidine, (S) -1- (1,1,1-trifluoro-3-cyclohexyl-2-ethyl) -4,4-dimethyl-3- Oxopyrazoline, (S) -1- (1,1,1-trifluoro-2-nonyl) -4,4-dimethyl-3-oxopyrazolidine, (S) -1- (1,1,1-tri Fluoro-2-decyl) -4,4-dimethyl-3-oxopyrazolidine, (S) -1- (1,1,1-to Fluoro-2-undecyl) -4,4-dimethyl-3-oxopyrazolidine, (S) -1- (1,1,1-trifluoro-2-dodecyl) -3-oxopyrazolidine and the like be able to.

本発明の一般式(1)で表される光学活性4,4−ジメチル−3−オキソピペラゾリジン誘導体で、Rが置換基を有しても良いフェニル基であるものとしては、具体的には例えば、(S)−1−(2,2,2−トリフルオロ−1−フェニル−1−エチル)−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−メチルフェニル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−メチルフェニル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−メチルフェニル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−エチルフェニル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−エチルフェニル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−エチルフェニル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−n−プロピルフェニル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−n−プロピルフェニル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−プロピルフェニル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−iso−プロピルフェニル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−iso−プロピルフェニル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−iso−プロピルフェニル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−n−ブチルフェニル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−n−ブチルフェニル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−ブチルフェニル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−iso−ブチルフェニル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−iso−ブチルフェニル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−iso−ブチルフェニル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−tert−ブチルフェニル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−tert−ブチルフェニル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−tert−ブチルフェニル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−ペンチルフェニル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−ヘキシルフェニル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−ヘプチルフェニル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−オクチルフェニル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−ノニルフェニル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−デシルフェニル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−メトキシフェニル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−メトキシフェニル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−メトキシフェニル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−エトキシフェニル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−エトキシフェニル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−エトキシフェニル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−n−プロポキシフェニル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−n−プロポキシフェニル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−プロポキシフェニル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−iso−プロポキシフェニル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−iso−プロポキシフェニル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−iso−プロポキシフェニル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−n−ブトキシフェニル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−n−ブトキシフェニル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−ブトキシフェニル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−iso−ブトキシフェニル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−iso−ブトキシフェニル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−iso−ブトキシフェニル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−tert−ブトキシフェニル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−tert−ブトキシフェニル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−tert−ブトキシフェニル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−ペントキシフェニル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−ヘキシルオキシフェニル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−ヘプチルオキシフェニル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−オクチルオキシフェニル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−ノニルオキシフェニル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−デシルオキシフェニル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−フルオロフェニル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−フルオロフェニル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−フルオロフェニル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−クロロフェニル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−クロロフェニル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−クロロフェニル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−ブロモフェニル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−ブロモフェニル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−ブロモフェニル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−シアノフェニル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−シアノフェニル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−シアノフェニル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−ニトロフェニル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−ニトロフェニル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−ニトロフェニル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン等を挙げることができる。 Specific examples of the optically active 4,4-dimethyl-3-oxopiperazolidine derivative represented by the general formula (1) of the present invention, wherein R 3 is a phenyl group which may have a substituent, For example, (S) -1- (2,2,2-trifluoro-1-phenyl-1-ethyl) -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2 , 2,2-trifluoro-1- (2-methylphenyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro -1- (3-methylphenyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-methyl) Phenyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2 , 2-trifluoro-1- (2-ethylphenyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1 -(3-Ethylphenyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-ethylphenyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (2-n-propylphenyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (3-n-propylphenyl) -1-ethyl] -4,4- Dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-n- (Lopylphenyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (2-iso-propylphenyl) -1- Ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (3-iso-propylphenyl) -1-ethyl] -4, 4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-iso-propylphenyl) -1-ethyl] -4,4-dimethyl-3 -Oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (2-n-butylphenyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine , (S) -1- [2,2,2-trifluoro-1- (3-n-butyl Enyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-n-butylphenyl) -1- Ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (2-iso-butylphenyl) -1-ethyl] -4, 4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (3-iso-butylphenyl) -1-ethyl] -4,4-dimethyl-3 -Oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-iso-butylphenyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine , (S) -1- [2,2,2-trifluoro-1- (2-tert-butylphenyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (3-tert-butylphenyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-tert-butylphenyl) -1-ethyl] -4,4- Dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-n-pentylphenyl) -1-ethyl] -4,4-dimethyl-3-oxo Pyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-n-hexylphenyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, ( S) -1- [2,2,2-trifluoro-1- (4-n-heptylphenyl) -1-e L] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-n-octylphenyl) -1-ethyl] -4, 4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-n-nonylphenyl) -1-ethyl] -4,4-dimethyl-3 -Oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-n-decylphenyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine (S) -1- [2,2,2-trifluoro-1- (2-methoxyphenyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (3-methoxyphenyl) -1-ethyl] -4,4-dimethyl-3 Oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-methoxyphenyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S ) -1- [2,2,2-trifluoro-1- (2-ethoxyphenyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2, 2,2-trifluoro-1- (3-ethoxyphenyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro- 1- (4-Ethoxyphenyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (2-n- (Propoxyphenyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1 -[2,2,2-trifluoro-1- (3-n-propoxyphenyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2 , 2-trifluoro-1- (4-n-propoxyphenyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro -1- (2-iso-propoxyphenyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (3 -Iso-propoxyphenyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-iso-propoxyphenyl) ) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S -1- [2,2,2-trifluoro-1- (2-n-butoxyphenyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2 , 2,2-trifluoro-1- (3-n-butoxyphenyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2- Trifluoro-1- (4-n-butoxyphenyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (2-Iso-butoxyphenyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (3-iso- Butoxyphenyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- 2,2,2-trifluoro-1- (4-iso-butoxyphenyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2 -Trifluoro-1- (2-tert-butoxyphenyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1 -(3-tert-butoxyphenyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-tert -Butoxyphenyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-n-pentoxyphenyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-n-hexyloxyphenyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [ 2,2,2-trifluoro-1- (4-n-heptyloxyphenyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2, 2-trifluoro-1- (4-n-octyloxyphenyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro -1- (4-n-nonyloxyphenyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- ( 4-n-decyloxyphenyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolid (S) -1- [2,2,2-trifluoro-1- (2-fluorophenyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (3-fluorophenyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2- Trifluoro-1- (4-fluorophenyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (2 -Chlorophenyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (3-chlorophenyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro -1- (4-chlorophenyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (2-bromophenyl) ) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (3-bromophenyl) -1-ethyl]- 4,4-Dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-bromophenyl) -1-ethyl] -4,4-dimethyl-3 -Oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (2-cyanophenyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, ( S) -1- [2,2,2-trifluoro-1- (3-cyanophenyl) -1-ethyl] -4 , 4-Dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-cyanophenyl) -1-ethyl] -4,4-dimethyl-3- Oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (2-nitrophenyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S ) -1- [2,2,2-trifluoro-1- (3-nitrophenyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2, 2,2-trifluoro-1- (4-nitrophenyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine and the like can be mentioned.

本発明の一般式(1)で表される光学活性4,4−ジメチル−3−オキソピペラゾリジン誘導体で、Rが置換基を有しても良い1−ナフチル基であるものとしては、具体的には例えば、(S)−1−[2,2,2−トリフルオロ−1−(1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−メチル−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−メチル−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−メチル−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−メチル−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−メチル−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−メチル−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−メチル−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−エチル−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−エチル−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−エチル−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−エチル−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−エチル−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−エチル−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−エチル−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−n−プロピル−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−n−プロピル−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−プロピル−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−n−プロピル−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−プロピル−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−n−プロピル−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−プロピル−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−iso−プロピル−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−iso−プロピル−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−iso−プロピル−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−iso−プロピル−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−iso−プロピル−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−iso−プロピル−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−iso−プロピル−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−n−ブチル−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−n−ブチル−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−ブチル−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−n−ブチル−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−ブチル−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−n−ブチル−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−ブチル−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−iso−ブチル−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−iso−ブチル−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−iso−ブチル−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−iso−ブチル−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−iso−ブチル−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−iso−ブチル−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−iso−ブチル−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−tert−ブチル−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−tert−ブチル−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−tert−ブチル−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−tert−ブチル−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−tert−ブチル−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−tert−ブチル−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−tert−ブチル−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−n−ペンチル−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−ペンチル−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−ペンチル−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−ペンチル−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−n−ヘキシル−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−ヘキシル−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−ヘキシル−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−ヘキシル−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−n−ヘプチル−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−ヘプチル−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−ヘプチル−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−ヘプチル−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−n−オクチル−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−オクチル−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−オクチル−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−オクチル−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−n−ノニル−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−ノニル−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−ノニル−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−ノニル−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−n−デシル−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−デシル−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−デシル−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−デシル−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−メトキシ
−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−メトキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−メトキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−メトキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−メトキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−メトキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−メトキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−エトキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−エトキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−エトキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−エトキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−エトキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−エトキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−エトキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−n−プロポキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−n−プロポキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−プロポキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−n−プロポキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−プロポキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−n−プロポキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−プロポキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−iso−プロポキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−iso−プロポキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−iso−プロポキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−iso−プロポキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−iso−プロポキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−iso−プロポキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−iso−プロポキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−n−ブトキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−n−ブトキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−ブトキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−n−ブトキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−ブトキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−n−ブトキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−ブトキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−iso−ブトキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−iso−ブトキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−iso−ブトキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−iso−ブトキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−iso−ブトキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−iso−ブトキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−iso−ブトキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−tert−ブトキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−tert−ブトキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−tert−ブトキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−tert−ブトキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−tert−ブトキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−tert−ブトキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−tert−ブトキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−n−ペントキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−ペントキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−ペントキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−ペントキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−n−ヘキシルオキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−ヘキシルオキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−ヘキシルオキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−ヘキシルオキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−n−ヘプチルオキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン(S)−1−[2,2,2−トリフルオロ−1−(4−n−ヘプチルオキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−ヘプチルオキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−ヘプチルオキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−n−オクチルオキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−オクチルオキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−オクチルオキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−オクチルオキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−n−ノニルオキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−ノニルオキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−ノニルオキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−ノニルオキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−n−デシルオキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−デシルオキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−デシルオキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−デシルオキシ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−フルオロ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−フルオロ−
1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−フルオロ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−フルオロ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−フルオロ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−フルオロ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−フルオロ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−クロロ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−クロロ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−クロロ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−クロロ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−クロロ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−クロロ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−クロロ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−ブロモ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−ブロモ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−ブロモ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−ブロモ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−ブロモ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−ブロモ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−ブロモ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−シアノ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−シアノ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−シアノ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−シアノ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−シアノ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−シアノ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−シアノ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−ニトロ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−ニトロ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−ニトロ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−ニトロ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−ニトロ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−ニトロ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−ニトロ−1−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン等を挙げることができる。
An optically active 4,4-dimethyl-3-oxopiperazolidine derivative represented by the general formula (1) of the present invention, wherein R 3 Specific examples of the 1-naphthyl group which may have a substituent include (S) -1- [2,2,2-trifluoro-1- (1-naphthyl) -1 -Ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (2-methyl-1-naphthyl) -1-ethyl]- 4,4-Dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (3-methyl-1-naphthyl) -1-ethyl] -4,4- Dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-methyl-1-naphthyl) -1-ethyl] -4,4-dimethyl-3- Oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (5-methyl-1-naphthyl) -1-ethyl -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (6-methyl-1-naphthyl) -1-ethyl] -4,4 -Dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (7-methyl-1-naphthyl) -1-ethyl] -4,4-dimethyl-3 -Oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (8-methyl-1-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazo Lysine, (S) -1- [2,2,2-trifluoro-1- (2-ethyl-1-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S ) -1- [2,2,2-trifluoro-1- (3-ethyl-1-naphthyl) -1-ethyl] -4,4-dimethyl Ru-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-ethyl-1-naphthyl) -1-ethyl] -4,4-dimethyl-3- Oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (5-ethyl-1-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine (S) -1- [2,2,2-trifluoro-1- (6-ethyl-1-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (7-ethyl-1-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [ 2,2,2-trifluoro-1- (8-ethyl-1-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopi Lazolidine, (S) -1- [2,2,2-trifluoro-1- (2-n-propyl-1-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (3-n-propyl-1-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S ) -1- [2,2,2-trifluoro-1- (4-n-propyl-1-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S)- 1- [2,2,2-trifluoro-1- (5-n-propyl-1-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (6-n-propyl-1-naphthyl) -1-ethyl] -4,4-dimethyl 3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (7-n-propyl-1-naphthyl) -1-ethyl] -4,4-dimethyl-3- Oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (8-n-propyl-1-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyra Zolidine, (S) -1- [2,2,2-trifluoro-1- (2-iso-propyl-1-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine (S) -1- [2,2,2-trifluoro-1- (3-iso-propyl-1-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, S) -1- [2,2,2-trifluoro-1- (4-iso-propyl-1-naphthyl) -1- Til] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (5-iso-propyl-1-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (6-iso-propyl-1-naphthyl) -1-ethyl] -4 , 4-Dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (7-iso-propyl-1-naphthyl) -1-ethyl] -4,4 -Dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (8-iso-propyl-1-naphthyl) -1-ethyl] -4,4-dimethyl -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (2-n-butyl) Til-1-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (3-n-butyl-) 1-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-n-butyl-1- Naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (5-n-butyl-1-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (6-n-butyl-1-naphthyl) -1 -Ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (7-n Butyl-1-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (8-n-butyl-) 1-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (2-iso-butyl-1- Naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (3-iso-butyl-1-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-iso-butyl-1-naphthyl) -1 -Ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro -1- (5-iso-butyl-1-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1 -(6-Iso-butyl-1-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- ( 7-iso-butyl-1-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (8- iso-butyl-1-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (2-tert- Butyl-1-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (3-tert-butyl-1-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2 , 2,2-trifluoro-1- (4-tert-butyl-1-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2 , 2-trifluoro-1- (5-tert-butyl-1-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2 -Trifluoro-1- (6-tert-butyl-1-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-tri Fluoro-1- (7-tert-butyl-1-naphthyl) -1-ethyl] -4,4-dimethyl-3 Oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (8-tert-butyl-1-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyra Zolidine, (S) -1- [2,2,2-trifluoro-1- (2-n-pentyl-1-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine (S) -1- [2,2,2-trifluoro-1- (4-n-pentyl-1-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, S) -1- [2,2,2-trifluoro-1- (6-n-pentyl-1-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (8-n-pentyl-1-naphthyl) -1-ethyl] -4 4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (2-n-hexyl-1-naphthyl) -1-ethyl] -4,4- Dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-n-hexyl-1-naphthyl) -1-ethyl] -4,4-dimethyl- 3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (6-n-hexyl-1-naphthyl) -1-ethyl] -4,4-dimethyl-3- Oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (8-n-hexyl-1-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyra Zolidine, (S) -1- [2,2,2-trifluoro-1- (2-n-heptyl-1-naphthyl) -1- Ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-n-heptyl-1-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (6-n-heptyl-1-naphthyl) -1-ethyl] -4 , 4-Dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (8-n-heptyl-1-naphthyl) -1-ethyl] -4,4 -Dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (2-n-octyl-1-naphthyl) -1-ethyl] -4,4-dimethyl -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-n-octyl-1-na Til) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (6-n-octyl-1-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (8-n-octyl-1-naphthyl) -1 -Ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (2-n-nonyl-1-naphthyl) -1-ethyl ] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-n-nonyl-1-naphthyl) -1-ethyl]- 4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (6-n-nonyl) 1-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (8-n-nonyl-1-) Naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (2-n-decyl-1-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-n-decyl-1-naphthyl) -1 -Ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (6-n-decyl-1-naphthyl) -1-ethyl ] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (8-n-deci] Ru-1-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (2-methoxy)
-1-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (3-methoxy-1-naphthyl) ) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-methoxy-1-naphthyl) -1- Ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (5-methoxy-1-naphthyl) -1-ethyl] -4 , 4-Dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (6-methoxy-1-naphthyl) -1-ethyl] -4,4-dimethyl -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (7-methoxy-1- Butyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (8-methoxy-1-naphthyl) -1 -Ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (2-ethoxy-1-naphthyl) -1-ethyl]- 4,4-Dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (3-ethoxy-1-naphthyl) -1-ethyl] -4,4- Dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-ethoxy-1-naphthyl) -1-ethyl] -4,4-dimethyl-3- Oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (5-ethoxy-1-naphthy) ) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (6-ethoxy-1-naphthyl) -1- Ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (7-ethoxy-1-naphthyl) -1-ethyl] -4 , 4-Dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (8-ethoxy-1-naphthyl) -1-ethyl] -4,4-dimethyl -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (2-n-propoxy-1-naphthyl) -1-ethyl] -4,4-dimethyl-3 -Oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (3-n-propoxy-1-na Butyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-n-propoxy-1-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (5-n-propoxy-1-naphthyl) -1 -Ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (6-n-propoxy-1-naphthyl) -1-ethyl ] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (7-n-propoxy-1-naphthyl) -1-ethyl]- 4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (8 n-propoxy-1-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (2-iso- Propoxy-1-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (3-iso-propoxy-) 1-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-iso-propoxy-1- Naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (5-iso-propoxy-1-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S)- -[2,2,2-trifluoro-1- (6-iso-propoxy-1-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [ 2,2,2-trifluoro-1- (7-iso-propoxy-1-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2, 2,2-trifluoro-1- (8-iso-propoxy-1-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2, 2-trifluoro-1- (2-n-butoxy-1-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2- Trifluoro-1- (3-n-butoxy-1-naphthyl) -1-ethyl] -4,4-dimethyl-3 -Oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-n-butoxy-1-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxo Pyrazolidine, (S) -1- [2,2,2-trifluoro-1- (5-n-butoxy-1-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazo Lysine, (S) -1- [2,2,2-trifluoro-1- (6-n-butoxy-1-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (7-n-butoxy-1-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S ) -1- [2,2,2-trifluoro-1- (8-n-butoxy-1-naphthyl) -1-ethyl] -4,4 Dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (2-iso-butoxy-1-naphthyl) -1-ethyl] -4,4-dimethyl- 3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (3-iso-butoxy-1-naphthyl) -1-ethyl] -4,4-dimethyl-3- Oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-iso-butoxy-1-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyra Zolidine, (S) -1- [2,2,2-trifluoro-1- (5-iso-butoxy-1-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine , (S) -1- [2,2,2-trifluoro-1- (6-iso-butoxy-1) Naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (7-iso-butoxy-1-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (8-iso-butoxy-1-naphthyl) -1 -Ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (2-tert-butoxy-1-naphthyl) -1-ethyl ] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (3-tert-butoxy-1-naphthyl) -1-ethyl]- 4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro Oro-1- (4-tert-butoxy-1-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro- 1- (5-tert-butoxy-1-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (6-tert-butoxy-1-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (7 -Tert-butoxy-1-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (8-tert -Butoxy-1-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyra Lysine, (S) -1- [2,2,2-trifluoro-1- (2-n-pentoxy-1-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-n-pentoxy-1-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S ) -1- [2,2,2-trifluoro-1- (6-n-pentoxy-1-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S)- 1- [2,2,2-trifluoro-1- (8-n-pentoxy-1-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (2-n-hexyloxy-1-naphthyl) -1-ethyl] -4, -Dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-n-hexyloxy-1-naphthyl) -1-ethyl] -4,4- Dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (6-n-hexyloxy-1-naphthyl) -1-ethyl] -4,4-dimethyl -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (8-n-hexyloxy-1-naphthyl) -1-ethyl] -4,4-dimethyl- 3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (2-n-heptyloxy-1-naphthyl) -1-ethyl] -4,4-dimethyl-3 -Oxopyrazolidine (S) -1- [2,2,2-trifluoro-1- (4-n-heptylo Xyl-1-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (6-n-heptyloxy) -1-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (8-n-heptyloxy-) 1-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (2-n-octyloxy-1) -Naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-n-octyloxy-1- Naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2 2-trifluoro-1- (6-n-octyloxy-1-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2 -Trifluoro-1- (8-n-octyloxy-1-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2- Trifluoro-1- (2-n-nonyloxy-1-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro -1- (4-n-nonyloxy-1-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1 -(6-n-nonyloxy-1-naphthyl) -1-ethyl] -4,4-dimethyl-3-o Sopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (8-n-nonyloxy-1-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (2-n-decyloxy-1-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S ) -1- [2,2,2-trifluoro-1- (4-n-decyloxy-1-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S)- 1- [2,2,2-trifluoro-1- (6-n-decyloxy-1-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (8-n-decyloxy-1-naphthyl) -1-e Til] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (2-fluoro-1-naphthyl) -1-ethyl] -4 , 4-Dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (3-fluoro-
1-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-fluoro-1-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (5-fluoro-1-naphthyl) -1-ethyl ] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (6-fluoro-1-naphthyl) -1-ethyl] -4, 4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (7-fluoro-1-naphthyl) -1-ethyl] -4,4-dimethyl- 3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (8-fluoro-1-na Til) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (2-chloro-1-naphthyl) -1 -Ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (3-chloro-1-naphthyl) -1-ethyl]- 4,4-Dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-chloro-1-naphthyl) -1-ethyl] -4,4- Dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (5-chloro-1-naphthyl) -1-ethyl] -4,4-dimethyl-3- Oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (6-chloro-1-naphthyl) -1-e L] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (7-chloro-1-naphthyl) -1-ethyl] -4 , 4-Dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (8-chloro-1-naphthyl) -1-ethyl] -4,4-dimethyl -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (2-bromo-1-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxo Pyrazolidine, (S) -1- [2,2,2-trifluoro-1- (3-bromo-1-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-bromo-1-naphthyl) -1-ethyl] -4,4-di Methyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (5-bromo-1-naphthyl) -1-ethyl] -4,4-dimethyl-3- Oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (6-bromo-1-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine (S) -1- [2,2,2-trifluoro-1- (7-bromo-1-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (8-bromo-1-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [ 2,2,2-trifluoro-1- (2-cyano-1-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxy Pyrazolidine, (S) -1- [2,2,2-trifluoro-1- (3-cyano-1-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S ) -1- [2,2,2-trifluoro-1- (4-cyano-1-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (5-cyano-1-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2 , 2-trifluoro-1- (6-cyano-1-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-tri Fluoro-1- (7-cyano-1-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, S) -1- [2,2,2-trifluoro-1- (8-cyano-1-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1 -[2,2,2-trifluoro-1- (2-nitro-1-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2, 2,2-trifluoro-1- (3-nitro-1-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2- Trifluoro-1- (4-nitro-1-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1 -(5-Nitro-1-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2, 2,2-trifluoro-1- (6-nitro-1-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2- Trifluoro-1- (7-nitro-1-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1 -(8-Nitro-1-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine and the like can be mentioned.

本発明の一般式(1)で表される光学活性4,4−ジメチル−3−オキソピペラゾリジン誘導体で、Rが置換基を有しても良い2−ナフチル基であるものとしては、具体的には例えば、(S)−1−[2,2,2−トリフルオロ−1−(2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−メチル−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−メチル−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−メチル−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−メチル−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−メチル−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−メチル−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−メチル−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−エチル−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−エチル−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−エチル−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−エチル−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−エチル−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−エチル−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−エチル−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−n−プロピル−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−n−プロピル−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−n−プロピル−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−プロピル−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−n−プロピル−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−プロピル−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−n−プロピル−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−プロピル−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−iso−プロピル−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−iso−プロピル−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−iso−プロピル−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−iso−プロピル−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−iso−プロピル−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−iso−プロピル−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−iso−プロピル−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−n−ブチル−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−n−ブチル−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−ブチル−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−n−ブチル−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−ブチル−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−n−ブチル−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−ブチル−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−iso−ブチル−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−iso−ブチル−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−iso−ブチル−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−iso−ブチル−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−iso−ブチル−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−iso−ブチル−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−iso−ブチル−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−iso−ブチル−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−tert−ブチル−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−tert−ブチル−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−tert−ブチル−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−tert−ブチル−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−tert−ブチル−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−tert−ブチル−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−tert−ブチル−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−tert−ブチル−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−n−ペンチル−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−ペンチル−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−ペンチル−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−ペンチル−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−n−ヘキシル−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−ヘキシル−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−ヘキシル−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−ヘキシル−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−n−ヘプチル−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−ヘプチル−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−ヘプチル−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−ヘプチル−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−n−オクチル−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−オクチル−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−オクチル−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−オクチル−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−n−ノニル−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−ノニル−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−ノニル−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−ノニル−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−n−デシル−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(
4−n−デシル−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−デシル−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−デシル−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−メトキシ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−メトキシ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−メトキシ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−メトキシ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−メトキシ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−メトキシ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−メトキシ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−エトキシ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−エトキシ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−エトキシ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−エトキシ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−エトキシ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−エトキシ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−エトキシ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−n−プロポキ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−n−プロポキ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−プロポキ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−n−プロポキ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−プロポキ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−n−プロポキ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−プロポキ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−iso−プロポキ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−iso−プロポキ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−iso−プロポキ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−iso−プロポキ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−iso−プロポキ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−iso−プロポキ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−iso−プロポキ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−n−ブトキシ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−n−ブトキシ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−ブトキシ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−n−ブトキシ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−ブトキシ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−n−ブトキシ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−ブトキシ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−iso−ブトキシ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−iso−ブトキシ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−iso−ブトキシ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−iso−ブトキシ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−iso−ブトキシ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−iso−ブトキシ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−iso−ブトキシ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−tert−ブトキシ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−tert−ブトキシ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−tert−ブトキシ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−tert−ブトキシ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−tert−ブトキシ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−tert−ブトキシ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−tert−ブトキシ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−n−ペントキシ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−ペントキシ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−ペントキシ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−ペントキシ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−n−ヘキシルオキシ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−ヘキシルオキシ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−ヘキシルオキシ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−ヘキシルオキシ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−n−ヘプチルオキシ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−ヘプチルオキシ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−ヘプチルオキシ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−ヘプチルオキシ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−n−オクチルオキシ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−オクチルオキシ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−オクチルオキシ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−オクチルオキシ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−n−ノニルオキシ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−ノニルオキシ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−ノニルオキシ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−ノニルオキシ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−n−デシルオキシ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−デシルオキシ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−デシルオキシ−2−ナフチル)−
1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−デシルオキシ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−フルオロ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−フルオロ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−フルオロ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−フルオロ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−フルオロ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−フルオロ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−フルオロ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−クロロ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−クロロ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−クロロ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−クロロ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−クロロ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−クロロ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−クロロ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−ブロモ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−ブロモ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−ブロモ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−ブロモ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−ブロモ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−ブロモ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−ブロモ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−シアノ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−シアノ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−シアノ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−シアノ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−シアノ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−シアノ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−シアノ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−ニトロ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−ニトロ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−ニトロ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−ニトロ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−ニトロ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−ニトロ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−ニトロ−2−ナフチル)−1−エチル]−4,4−ジメチル−3−オキソピラゾリジン等を挙げることができる。
An optically active 4,4-dimethyl-3-oxopiperazolidine derivative represented by the general formula (1) of the present invention, wherein R 3 Specific examples of the 2-naphthyl group that may have a substituent include (S) -1- [2,2,2-trifluoro-1- (2-naphthyl) -1 -Ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (1-methyl-2-naphthyl) -1-ethyl]- 4,4-Dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (3-methyl-2-naphthyl) -1-ethyl] -4,4- Dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-methyl-2-naphthyl) -1-ethyl] -4,4-dimethyl-3- Oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (5-methyl-2-naphthyl) -1-ethyl -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (6-methyl-2-naphthyl) -1-ethyl] -4,4 -Dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (7-methyl-2-naphthyl) -1-ethyl] -4,4-dimethyl-3 -Oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (8-methyl-2-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazo Lysine, (S) -1- [2,2,2-trifluoro-1- (1-ethyl-2-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S ) -1- [2,2,2-trifluoro-1- (3-ethyl-2-naphthyl) -1-ethyl] -4,4-dimethyl Ru-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-ethyl-2-naphthyl) -1-ethyl] -4,4-dimethyl-3- Oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (5-ethyl-2-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine (S) -1- [2,2,2-trifluoro-1- (6-ethyl-2-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (7-ethyl-2-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [ 2,2,2-trifluoro-1- (8-ethyl-2-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopi Lazolidine, (S) -1- [2,2,2-trifluoro-1- (1-n-propyl-2-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (2-n-propyl-2-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S ) -1- [2,2,2-trifluoro-1- (3-n-propyl-2-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S)- 1- [2,2,2-trifluoro-1- (4-n-propyl-2-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (5-n-propyl-2-naphthyl) -1-ethyl] -4,4-dimethyl 3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (6-n-propyl-2-naphthyl) -1-ethyl] -4,4-dimethyl-3- Oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (7-n-propyl-2-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyra Zolidine, (S) -1- [2,2,2-trifluoro-1- (8-n-propyl-2-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine (S) -1- [2,2,2-trifluoro-1- (1-iso-propyl-2-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, S) -1- [2,2,2-trifluoro-1- (3-iso-propyl-2-naphthyl) -1-eth ] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-iso-propyl-2-naphthyl) -1-ethyl]- 4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (5-iso-propyl-2-naphthyl) -1-ethyl] -4, 4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (6-iso-propyl-2-naphthyl) -1-ethyl] -4,4- Dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (7-iso-propyl-2-naphthyl) -1-ethyl] -4,4-dimethyl- 3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (8-iso-propyl) (Lopyl-2-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (1-n-butyl-) 2-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (3-n-butyl-2- Naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-n-butyl-2-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (5-n-butyl-2-naphthyl) -1 -Ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (6- -Butyl-2-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (7-n-butyl) -2-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (8-n-butyl-2) -Naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (1-iso-butyl-2-naphthyl) ) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (2-iso-butyl-2-naphthyl)- 1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro 1- (3-Iso-butyl-2-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-Iso-butyl-2-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (5 -Iso-butyl-2-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (6-iso) -Butyl-2-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (7-iso-butyl) -2-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2 , 2,2-trifluoro-1- (8-iso-butyl-2-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2 , 2-trifluoro-1- (1-tert-butyl-2-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2 -Trifluoro-1- (2-tert-butyl-2-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-tri Fluoro-1- (3-tert-butyl-2-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro- 1- (4-tert-butyl-2-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxy Pyrazolidine, (S) -1- [2,2,2-trifluoro-1- (5-tert-butyl-2-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (6-tert-butyl-2-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S ) -1- [2,2,2-trifluoro-1- (7-tert-butyl-2-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S)- 1- [2,2,2-trifluoro-1- (8-tert-butyl-2-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (1-n-pentyl-2-naphthyl) -1-ethyl -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-n-pentyl-2-naphthyl) -1-ethyl] -4 , 4-Dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (6-n-pentyl-2-naphthyl) -1-ethyl] -4,4 -Dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (8-n-pentyl-2-naphthyl) -1-ethyl] -4,4-dimethyl -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (1-n-hexyl-2-naphthyl) -1-ethyl] -4,4-dimethyl-3 -Oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-n-hexyl-2-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (6-n-hexyl-2-naphthyl) -1 -Ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (8-n-hexyl-2-naphthyl) -1-ethyl ] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (1-n-heptyl-2-naphthyl) -1-ethyl]- 4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-n-heptyl-2-naphthyl) -1-ethyl] -4, 4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (6-n-heptyl- -Naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (8-n-heptyl-2-naphthyl) ) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (1-n-octyl-2-naphthyl)- 1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-n-octyl-2-naphthyl) -1- Ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (6-n-octyl-2-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (8- -Octyl-2-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (1-n-nonyl) -2-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-n-nonyl-2) -Naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (6-n-nonyl-2-naphthyl) ) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (8-n-nonyl-2-naphthyl)- 1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- ( 1-n-decyl-2-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (
4-n-decyl-2-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (6- n-decyl-2-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (8-n- Decyl-2-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (1-methoxy-2-) Naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (3-methoxy-2-naphthyl) -1 -Ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- ( -Methoxy-2-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (5-methoxy-2) -Naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (6-methoxy-2-naphthyl)- 1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (7-methoxy-2-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (8-methoxy-2-naphthyl) -1-ethyl] -4,4 -Dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (1-e Xyl-2-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (3-ethoxy-2-) Naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-ethoxy-2-naphthyl) -1 -Ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (5-ethoxy-2-naphthyl) -1-ethyl]- 4,4-Dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (6-ethoxy-2-naphthyl) -1-ethyl] -4,4- Dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (7-ethoxy- 2-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (8-ethoxy-2-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (1-n-propoxy-2-naphthyl) -1 -Ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (3-n-propoxy-2-naphthyl) -1-ethyl ] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-n-propoxy-2-naphthyl) -1-ethyl]- 4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (5-n- (Lopoxy-2-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (6-n-propoxy) 2-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (7-n-propoxy-2-one) Naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (8-n-propoxy-2-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (1-iso-propoxy-2-naphthyl) -1 -Ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro -1- (3-iso-propoxy-2-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1 -(4-Iso-propoxy-2-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- ( 5-iso-propoxy-2-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (6- iso-propoxy-2-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (7-iso- Propoxy-2-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S ) -1- [2,2,2-trifluoro-1- (8-iso-propoxy-2-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S)- 1- [2,2,2-trifluoro-1- (1-n-butoxy-2-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (3-n-butoxy-2-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2 , 2,2-trifluoro-1- (4-n-butoxy-2-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2 , 2-Trifluoro-1- (5-n-butoxy-2-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxo Lazolidine, (S) -1- [2,2,2-trifluoro-1- (6-n-butoxy-2-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (7-n-butoxy-2-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S ) -1- [2,2,2-trifluoro-1- (8-n-butoxy-2-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S)- 1- [2,2,2-trifluoro-1- (1-iso-butoxy-2-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (3-iso-butoxy-2-naphthyl) -1-ethyl] -4,4 Dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-iso-butoxy-2-naphthyl) -1-ethyl] -4,4-dimethyl- 3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (5-iso-butoxy-2-naphthyl) -1-ethyl] -4,4-dimethyl-3- Oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (6-iso-butoxy-2-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyra Zolidine, (S) -1- [2,2,2-trifluoro-1- (7-iso-butoxy-2-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine , (S) -1- [2,2,2-trifluoro-1- (8-iso-butoxy-2- Naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (1-tert-butoxy-2-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (3-tert-butoxy-2-naphthyl) -1 -Ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-tert-butoxy-2-naphthyl) -1-ethyl ] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (5-tert-butoxy-2-naphthyl) -1-ethyl]- 4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-tri Fluoro-1- (6-tert-butoxy-2-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro- 1- (7-tert-butoxy-2-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (8-tert-butoxy-2-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (1 -N-pentoxy-2-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-n -Pentoxy-2-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazoli (S) -1- [2,2,2-trifluoro-1- (6-n-pentoxy-2-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (8-n-pentoxy-2-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S ) -1- [2,2,2-trifluoro-1- (1-n-hexyloxy-2-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-n-hexyloxy-2-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S)- 1- [2,2,2-trifluoro-1- (6-n-hexyloxy-2-naphthyl) -1-ethyl] -4 , 4-Dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (8-n-hexyloxy-2-naphthyl) -1-ethyl] -4, 4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (1-n-heptyloxy-2-naphthyl) -1-ethyl] -4,4 -Dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-n-heptyloxy-2-naphthyl) -1-ethyl] -4,4- Dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (6-n-heptyloxy-2-naphthyl) -1-ethyl] -4,4-dimethyl -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (8-n-hept Ruoxy-2-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (1-n-octyloxy) -2-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-n-octyloxy-) 2-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (6-n-octyloxy-2) -Naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (8-n-octyloxy-2-) Naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [ , 2,2-trifluoro-1- (1-n-nonyloxy-2-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2 , 2-trifluoro-1- (4-n-nonyloxy-2-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2 -Trifluoro-1- (6-n-nonyloxy-2-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-tri Fluoro-1- (8-n-nonyloxy-2-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro- 1- (1-n-decyloxy-2-naphthyl) -1-ethyl] -4,4-dimethyl-3-o Xopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-n-decyloxy-2-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (6-n-decyloxy-2-naphthyl)-
1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (8-n-decyloxy-2-naphthyl) -1- Ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (1-fluoro-2-naphthyl) -1-ethyl] -4 , 4-Dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (3-fluoro-2-naphthyl) -1-ethyl] -4,4-dimethyl -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-fluoro-2-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxo Pyrazolidine, (S) -1- [2,2,2-trifluoro-1- (5-fluoro-2-naphthyl) 1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (6-fluoro-2-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (7-fluoro-2-naphthyl) -1-ethyl] -4,4 -Dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (8-fluoro-2-naphthyl) -1-ethyl] -4,4-dimethyl-3 -Oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (1-chloro-2-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazo Lysine, (S) -1- [2,2,2-trifluoro-1- (3-chloro-2-naphthyl) -1-ethyl ] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-chloro-2-naphthyl) -1-ethyl] -4, 4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (5-chloro-2-naphthyl) -1-ethyl] -4,4-dimethyl- 3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (6-chloro-2-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyra Zolidine, (S) -1- [2,2,2-trifluoro-1- (7-chloro-2-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, ( S) -1- [2,2,2-trifluoro-1- (8-chloro-2-naphthyl) -1-ethyl] -4,4-dimethyl Tyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (1-bromo-2-naphthyl) -1-ethyl] -4,4-dimethyl-3- Oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (3-bromo-2-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine (S) -1- [2,2,2-trifluoro-1- (4-bromo-2-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (5-bromo-2-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [ 2,2,2-trifluoro-1- (6-bromo-2-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxo Lazolidine, (S) -1- [2,2,2-trifluoro-1- (7-bromo-2-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S ) -1- [2,2,2-trifluoro-1- (8-bromo-2-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (1-cyano-2-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2 , 2-trifluoro-1- (3-cyano-2-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-tri Fluoro-1- (4-cyano-2-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, ( ) -1- [2,2,2-trifluoro-1- (5-cyano-2-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (6-cyano-2-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2 , 2-trifluoro-1- (7-cyano-2-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-tri Fluoro-1- (8-cyano-2-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (1-nitro-2-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2 , 2-trifluoro-1- (3-nitro-2-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-tri Fluoro-1- (4-nitro-2-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (5-Nitro-2-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (6-nitro -2-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (7-nitro-2-naphthyl) ) -1-ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro -1- (8-nitro-2-naphthyl) -1-ethyl] -4,4-dimethyl-3-oxo-pyrazolidine and the like.

本発明の一般式(1)で表される光学活性4,4−ジメチル−3−オキソピペラゾリジン誘導体で、Rが置換基を有しても良いアリールエチレニル基であるものとしては、具体的には例えば、(S)−1−[1−(トリフルオロメチル)−3−フェニル−2−プロペン]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(2−メチルフェニル)−2−プロペン)]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(3−メチルフェニル)−2−プロペン)]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(4−メチルフェニル)−2−プロペン)]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(2−エチルフェニル)−2−プロペン)]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(3−エチルフェニル)−2−プロペン)]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(4−エチルフェニル)−2−プロペン)]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(2−n−プロピルフェニル)−2−プロペン)]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(3−n−プロピルフェニル)−2−プロペン)]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(4−n−プロピルフェニル)−2−プロペン)]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(2−iso−プロピルフェニル)−2−プロペン)]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(3−iso−プロピルフェニル)−2−プロペン)]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(4−iso−プロピルフェニル)−2−プロペン)]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(2−n−ブチルフェニル)−2−プロペン)]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(3−n−ブチルフェニル)−2−プロペン)]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(4−n−ブチルフェニル)−2−プロペン)]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(2−sec−ブチルフェニル)−2−プロペン)]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(3−sec−ブチルフェニル)−2−プロペン)]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(4−sec−ブチルフェニル)−2−プロペン)]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(2−tert−ブチルフェニル)−2−プロペン)]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(3−tert−ブチルフェニル)−2−プロペン)]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(4−tert−ブチルフェニル)−2−プロペン)]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(2−メトキシフェニル)−2−プロペン)]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(3−メトキシフェニル)−2−プロペン)]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(4−メトキシフェニル)−2−プロペン)]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(2−エトキシフェニル)−2−プロペン)]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(3−エトキシフェニル)−2−プロペン)]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(4−エトキシフェニル)−2−プロペン)]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(2−n−プロポキシフェニル)−2−プロペン)]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(3−n−プロポキシフェニル)−2−プロペン)]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(4−n−プロポキシフェニル)−2−プロペン)]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(2−iso−プロポキシフェニル)−2−プロペン)]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(3−iso−プロポキシフェニル)−2−プロペン)]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(4−iso−プロポキシフェニル)−2−プロペン)]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(2−n−ブトキシフェニル)−2−プロペン)]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(3−n−ブトキシフェニル)−2−プロペン)]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(4−n−ブトキシフェニル)−2−プロペン)]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(2−sec−ブトキシフェニル)−2−プロペン)]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(3−sec−ブトキシフェニル)−2−プロペン)]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(4−sec−ブトキシフェニル)−2−プロペン)]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(2−tert−ブトキシフェニル)−2−プロペン)]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(3−tert−ブトキシフェニル)−2−プロペン)]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(4−tert−ブトキシフェニル)−2−プロペン)]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(2−フルオロフェニル)−2−プロペン)]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(3−フルオロフェニル)−2−プロペン)]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(4−フルオロフェニル)−2−プロペン)]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(2−クロロフェニル)−2−プロペン)]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(3−クロロフェニル)−2−プロペン)]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(4−クロロフェニル)−2−プロペン)]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(2−ブロモフェニル)−2−プロペン)]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(3−ブロモフェニル)−2−プロペン)]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(4−ブロモフェニル)−2−プロペン)]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(2−シアノフェニル)−2−プロペン)]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(3−シアノフェニル)−2−プロペン)]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(4−シアノフェニル)−2−プロペン)]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(2−ニトロフェニル)−2−プロペン)]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(3−ニトロフェニル)−2−プロペン)]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(4−ニトロフェニル)−2−プロペン)]−4,4−ジメチル−3−オキソピラゾリジン等を挙げることができる。 In the optically active 4,4-dimethyl-3-oxopiperazolidine derivative represented by the general formula (1) of the present invention, R 3 is an arylethylenyl group which may have a substituent. Specifically, for example, (S) -1- [1- (trifluoromethyl) -3-phenyl-2-propene] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [ 1- (trifluoromethyl) -3- (2-methylphenyl) -2-propene)]-4,4-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (3-methylphenyl) -2-propene)]-4,4-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (4-methyl) Phenyl) -2-propene)]-4,4-dimethyl-3-oxopi Lazolidine, (S) -1- [1- (trifluoromethyl) -3- (2-ethylphenyl) -2-propene)]-4,4-dimethyl-3-oxopyrazolidine, (S) -1 -[1- (trifluoromethyl) -3- (3-ethylphenyl) -2-propene)]-4,4-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoro Methyl) -3- (4-ethylphenyl) -2-propene)]-4,4-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (2 -N-propylphenyl) -2-propene)]-4,4-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (3-n-propylphenyl) ) -2-propene)]-4,4-dimethyl-3-oxopyrazo Gin, (S) -1- [1- (trifluoromethyl) -3- (4-n-propylphenyl) -2-propene)]-4,4-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (2-iso-propylphenyl) -2-propene)]-4,4-dimethyl-3-oxopyrazolidine, (S) -1- [1 -(Trifluoromethyl) -3- (3-iso-propylphenyl) -2-propene)]-4,4-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl ) -3- (4-Iso-propylphenyl) -2-propene)]-4,4-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- ( 2-n-butylphenyl) -2-propene)]-4,4-di Tyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (3-n-butylphenyl) -2-propene)]-4,4-dimethyl-3-oxo Pyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (4-n-butylphenyl) -2-propene)]-4,4-dimethyl-3-oxopyrazolidine, ( S) -1- [1- (trifluoromethyl) -3- (2-sec-butylphenyl) -2-propene)]-4,4-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (3-sec-butylphenyl) -2-propene)]-4,4-dimethyl-3-oxopyrazolidine, (S) -1- [1- (tri Fluoromethyl) -3- (4-sec-butylphenyl) -2-propene) ] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (2-tert-butylphenyl) -2-propene)]-4,4 -Dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (3-tert-butylphenyl) -2-propene)]-4,4-dimethyl-3- Oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (4-tert-butylphenyl) -2-propene)]-4,4-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (2-methoxyphenyl) -2-propene)]-4,4-dimethyl-3-oxopyrazolidine, (S) -1- [ 1- (trifluoromethyl) -3- (3-methoxyphenyl -2-propene)]-4,4-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (4-methoxyphenyl) -2-propene)]- 4,4-Dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (2-ethoxyphenyl) -2-propene)]-4,4-dimethyl-3 -Oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (3-ethoxyphenyl) -2-propene)]-4,4-dimethyl-3-oxopyrazolidine, ( S) -1- [1- (trifluoromethyl) -3- (4-ethoxyphenyl) -2-propene)]-4,4-dimethyl-3-oxopyrazolidine, (S) -1- [1 -(Trifluoromethyl) -3- (2-n-propoxyphenyl) -2-propene)]-4,4-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (3-n-propoxyphenyl) -2-propene) ] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (4-n-propoxyphenyl) -2-propene)]-4,4 -Dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (2-iso-propoxyphenyl) -2-propene)]-4,4-dimethyl-3- Oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (3-iso-propoxyphenyl) -2-propene)]-4,4-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3 -(4-Iso-propoxyphenyl) -2-propene)]-4,4-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (2-n -Butoxyphenyl) -2-propene)]-4,4-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (3-n-butoxyphenyl)- 2-propene)]-4,4-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (4-n-butoxyphenyl) -2-propene)] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (2-sec-butoxyphenyl) -2-propene)]-4,4- Dimethyl-3-oxopyrazolidine, (S) -1- [1- ( Trifluoromethyl) -3- (3-sec-butoxyphenyl) -2-propene)]-4,4-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl)- 3- (4-sec-butoxyphenyl) -2-propene)]-4,4-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (2- tert-butoxyphenyl) -2-propene)]-4,4-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (3-tert-butoxyphenyl) -2-propene)]-4,4-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (4-tert-butoxyphenyl) -2-propene) ] -4,4-dimethyl-3- Xopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (2-fluorophenyl) -2-propene)]-4,4-dimethyl-3-oxopyrazolidine, (S) -1 -[1- (trifluoromethyl) -3- (3-fluorophenyl) -2-propene)]-4,4-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoro Methyl) -3- (4-fluorophenyl) -2-propene)]-4,4-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (2 -Chlorophenyl) -2-propene)]-4,4-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (3-chlorophenyl) -2-propene) ] -4,4-dimethyl-3-oxopyrazo Lysine, (S) -1- [1- (trifluoromethyl) -3- (4-chlorophenyl) -2-propene)]-4,4-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (2-bromophenyl) -2-propene)]-4,4-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl ) -3- (3-Bromophenyl) -2-propene)]-4,4-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (4- Bromophenyl) -2-propene)]-4,4-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (2-cyanophenyl) -2-propene )]-4,4-dimethyl-3-oxopyrazolidine, (S)- -[1- (trifluoromethyl) -3- (3-cyanophenyl) -2-propene)]-4,4-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoro Methyl) -3- (4-cyanophenyl) -2-propene)]-4,4-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (2 -Nitrophenyl) -2-propene)]-4,4-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (3-nitrophenyl) -2- Propene)]-4,4-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (4-nitrophenyl) -2-propene)]-4,4 -Dimethyl-3-oxopyrazolidine etc. can be mentioned.

本発明の一般式(1)で表される光学活性4,4−ジメチル−3−オキソピペラゾリジン誘導体で、Rが置換基を有しても良いアリールアルキル基であるものとしては、具体的には例えば、(S)−1−[1−(トリフルオロメチル)−2−フェニルエチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−フェニルプロピル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−4−フェニルブチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−5−フェニルペンチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−6−フェニルヘキシル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−2−(2−メチルフェニル)エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−2−(3−メチルフェニル)エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−2−(4−メチルフェニル)エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(2−メチルフェニル)プロピル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(3−メチルフェニル)プロピル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(4−メチルフェニル)プロピル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−4−(2−メチルフェニル)ブチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−4−(3−メチルフェニル)ブチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−4−(4−メチルフェニル)ブチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−5−(2−メチルフェニル)ペンチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−5−(3−メチルフェニル)ペンチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−5−(4−メチルフェニル)ペンチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−2−(2−エチルフェニル)エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−2−(3−エチルフェニル)エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−2−(4−エチルフェニル)エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(2−エチルフェニル)プロピル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(3−エチルフェニル)プロピル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(4−エチルフェニル)プロピル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−4−(2−エチルフェニル)ブチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−4−(3−エチルフェニル)ブチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−4−(4−エチルフェニル)ブチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−5−(2−エチルフェニル)ペンチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−5−(3−エチルフェニル)ペンチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−5−(4−エチルフェニル)ペンチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−2−(2−メトキシフェニル)エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−2−(3−メトキシフェニル)エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−2−(4−メトキシフェニル)エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(2−メトキシフェニル)プロピル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(3−メトキシフェニル)プロピル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(4−メトキシフェニル)プロピル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−4−(2−メトキシフェニル)ブチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−4−(3−メトキシフェニル)ブチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−4−(4−メトキシフェニル)ブチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−5−(2−メトキシフェニル)ペンチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−5−(3−メトキシフェニル)ペンチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−5−(4−メトキシフェニル)ペンチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−2−(2−エトキシフェニル)エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−2−(3−エトキシフェニル)エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−2−(4−エトキシフェニル)エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(2−エトキシフェニル)プロピル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(3−エトキシフェニル)プロピル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(4−エトキシフェニル)プロピル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−4−(2−エトキシフェニル)ブチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−4−(3−エトキシフェニル)ブチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−4−(4−エトキシフェニル)ブチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−5−(2−エトキシフェニル)ペンチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−5−(3−エトキシフェニル)ペンチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−5−(4−エトキシフェニル)ペンチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−2−(2−フルオロフェニル)エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−2−(3−フルオロフェニル)エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−2−(4−フルオロフェニル)エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(2−フルオロフェニル)プロピル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(3−フルオロフェニル)プロピル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(4−フルオロフェニル)プロピル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−4−(2−フルオロフェニル)ブチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−4−(3−フルオロフェニル)ブチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−4−(4−フルオロフェニル)ブチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−5−(2−フルオロフェニル)ペンチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−5−(3−フルオロフェニル)ペンチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−5−(4−フルオロフェニル)ペンチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−2−(2−クロロフェニル)エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−2−(3−クロロフェニル)エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−2−(4−クロロフェニル)エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(2−クロロフェニル)プロピル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(3−クロロフェニル)プロピル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(4−クロロフェニル)プロピル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−4−(2−クロロフェニル)ブチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−4−(3−クロロフェニル)ブチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−4−(4−クロロフェニル)ブチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−5−(2−クロロフェニル)ペンチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−5−(3−クロロフェニル)ペンチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−5−(4−クロロフェニル)ペンチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−2−(2−ブロモフェニル)エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−2−(3−ブロモフェニル)エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−2−(4−ブロモフェニル)エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(2−ブロモフェニル)プロピル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(3−ブロモフェニル)プロピル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(4−ブロモフェニル)プロピル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1
−[1−(トリフルオロメチル)−4−(2−ブロモフェニル)ブチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−4−(3−ブロモフェニル)ブチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−4−(4−ブロモフェニル)ブチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−5−(2−ブロモフェニル)ペンチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−5−(3−ブロモフェニル)ペンチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−5−(4−ブロモフェニル)ペンチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−2−(2−シアノフェニル)エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−2−(3−シアノフェニル)エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−2−(4−シアノフェニル)エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(2−シアノフェニル)プロピル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(3−シアノフェニル)プロピル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(4−シアノフェニル)プロピル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−4−(2−シアノフェニル)ブチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−4−(3−シアノフェニル)ブチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−4−(4−シアノフェニル)ブチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−5−(2−シアノフェニル)ペンチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−5−(3−シアノフェニル)ペンチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−5−(4−シアノフェニル)ペンチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−2−(2−ニトロフェニル)エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−2−(3−ニトロフェニル)エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−2−(4−ニトロフェニル)エチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(2−ニトロフェニル)プロピル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(3−ニトロフェニル)プロピル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(4−ニトロフェニル)プロピル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−4−(2−ニトロフェニル)ブチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−4−(3−ニトロフェニル)ブチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−4−(4−ニトロフェニル)ブチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−5−(2−ニトロフェニル)ブチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−5−(3−ニトロフェニル)ブチル]−4,4−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−5−(4−ニトロフェニル)ブチル]−4,4−ジメチル−3−オキソピラゾリジン等を挙げることができる。
Examples of the optically active 4,4-dimethyl-3-oxopiperazolidine derivative represented by the general formula (1) of the present invention, in which R 3 is an arylalkyl group which may have a substituent, include For example, (S) -1- [1- (trifluoromethyl) -2-phenylethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [1- (tri (Fluoromethyl) -3-phenylpropyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -4-phenylbutyl] -4,4-dimethyl- 3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -5-phenylpentyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [1- (Trifluoromethyl) -6-phenylhexyl]- 4,4-Dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -2- (2-methylphenyl) ethyl] -4,4-dimethyl-3-oxopyrazo Lysine, (S) -1- [1- (trifluoromethyl) -2- (3-methylphenyl) ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [1- (Trifluoromethyl) -2- (4-methylphenyl) ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (2- Methylphenyl) propyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (3-methylphenyl) propyl] -4,4-dimethyl -3-oxopyrazolidine, (S) -1- [1- ( (Rifluoromethyl) -3- (4-methylphenyl) propyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -4- (2-methyl) Phenyl) butyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -4- (3-methylphenyl) butyl] -4,4-dimethyl- 3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -4- (4-methylphenyl) butyl] -4,4-dimethyl-3-oxopyrazolidine, (S)- 1- [1- (trifluoromethyl) -5- (2-methylphenyl) pentyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl)- 5- (3-Methylphenyl) pentyl] -4 4-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -5- (4-methylphenyl) pentyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -2- (2-ethylphenyl) ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [1- (tri Fluoromethyl) -2- (3-ethylphenyl) ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -2- (4-ethylphenyl) ) Ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (2-ethylphenyl) propyl] -4,4-dimethyl-3 -Oxopyrazolidine, (S) -1- [1- (tri Fluoromethyl) -3- (3-ethylphenyl) propyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (4-ethylphenyl) ) Propyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -4- (2-ethylphenyl) butyl] -4,4-dimethyl-3 -Oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -4- (3-ethylphenyl) butyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1 -[1- (trifluoromethyl) -4- (4-ethylphenyl) butyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -5 -(2-Ethylphenyl) pentyl] -4,4 Dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -5- (3-ethylphenyl) pentyl] -4,4-dimethyl-3-oxopyrazolidine, (S ) -1- [1- (trifluoromethyl) -5- (4-ethylphenyl) pentyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) ) -2- (2-methoxyphenyl) ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -2- (3-methoxyphenyl) ethyl ] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -2- (4-methoxyphenyl) ethyl] -4,4-dimethyl-3-oxo Pyrazolidine, (S) -1- [1- ( (Rifluoromethyl) -3- (2-methoxyphenyl) propyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (3-methoxy Phenyl) propyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (4-methoxyphenyl) propyl] -4,4-dimethyl- 3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -4- (2-methoxyphenyl) butyl] -4,4-dimethyl-3-oxopyrazolidine, (S)- 1- [1- (trifluoromethyl) -4- (3-methoxyphenyl) butyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl)- 4- (4-Methoxyphenyl) bu Til] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -5- (2-methoxyphenyl) pentyl] -4,4-dimethyl-3- Oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -5- (3-methoxyphenyl) pentyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -5- (4-methoxyphenyl) pentyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -2- (2-Ethoxyphenyl) ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -2- (3-ethoxyphenyl) ethyl] -4, 4-dimethyl-3-oxopyrazolidine, S) -1- [1- (trifluoromethyl) -2- (4-ethoxyphenyl) ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoro Methyl) -3- (2-ethoxyphenyl) propyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (3-ethoxyphenyl) Propyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (4-ethoxyphenyl) propyl] -4,4-dimethyl-3- Oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -4- (2-ethoxyphenyl) butyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [1- (Trifluoromethyl) -4- (3 Ethoxyphenyl) butyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -4- (4-ethoxyphenyl) butyl] -4,4-dimethyl -3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -5- (2-ethoxyphenyl) pentyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -5- (3-ethoxyphenyl) pentyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -5- (4-Ethoxyphenyl) pentyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -2- (2-fluorophenyl) ethyl] -4,4-dimethyl-3- Oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -2- (3-fluorophenyl) ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -2- (4-fluorophenyl) ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (2-fluorophenyl) propyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (3-fluorophenyl) propyl] -4, 4-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (4-fluorophenyl) propyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [1- (Trifluor Methyl) -4- (2-fluorophenyl) butyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -4- (3-fluorophenyl) Butyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -4- (4-fluorophenyl) butyl] -4,4-dimethyl-3- Oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -5- (2-fluorophenyl) pentyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -5- (3-fluorophenyl) pentyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -5 (4-Fluorophenyl) pentyl]- , 4-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -2- (2-chlorophenyl) ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -2- (3-chlorophenyl) ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoro Methyl) -2- (4-chlorophenyl) ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (2-chlorophenyl) propyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (3-chlorophenyl) propyl] -4,4-dimethyl-3-oxopyrazo Lysine, (S) -1- [1- (G (Rifluoromethyl) -3- (4-chlorophenyl) propyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -4- (2-chlorophenyl) Butyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -4- (3-chlorophenyl) butyl] -4,4-dimethyl-3-oxo Pyrazolidine, (S) -1- [1- (trifluoromethyl) -4- (4-chlorophenyl) butyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [1 -(Trifluoromethyl) -5- (2-chlorophenyl) pentyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -5- (3- Chlorophenyl) pentyl] -4, -Dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -5- (4-chlorophenyl) pentyl] -4,4-dimethyl-3-oxopyrazolidine, (S ) -1- [1- (trifluoromethyl) -2- (2-bromophenyl) ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) ) -2- (3-Bromophenyl) ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -2- (4-bromophenyl) ethyl ] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (2-bromophenyl) propyl] -4,4-dimethyl-3-oxo Pyrazolidine, (S) -1- [1- (tri (Luoromethyl) -3- (3-bromophenyl) propyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (4-bromophenyl) Propyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1
-[1- (trifluoromethyl) -4- (2-bromophenyl) butyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -4 -(3-Bromophenyl) butyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -4- (4-bromophenyl) butyl] -4 , 4-Dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -5- (2-bromophenyl) pentyl] -4,4-dimethyl-3-oxopyrazolidine (S) -1- [1- (trifluoromethyl) -5- (3-bromophenyl) pentyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [1- ( Trifluoromethyl) -5- (4-bromophenyl) pen L] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -2- (2-cyanophenyl) ethyl] -4,4-dimethyl-3- Oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -2- (3-cyanophenyl) ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -2- (4-cyanophenyl) ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (2-cyanophenyl) propyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (3-cyanophenyl) propyl] -4, 4-dimethyl-3-oxopyrazolidine, (S) -1- 1- (trifluoromethyl) -3- (4-cyanophenyl) propyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -4- ( 2-cyanophenyl) butyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -4- (3-cyanophenyl) butyl] -4,4 -Dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -4- (4-cyanophenyl) butyl] -4,4-dimethyl-3-oxopyrazolidine, ( S) -1- [1- (trifluoromethyl) -5- (2-cyanophenyl) pentyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoro Methyl) -5- (3-cyanophenyl) pentyl ] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -5- (4-cyanophenyl) pentyl] -4,4-dimethyl-3-oxo Pyrazolidine, (S) -1- [1- (trifluoromethyl) -2- (2-nitrophenyl) ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [ 1- (trifluoromethyl) -2- (3-nitrophenyl) ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -2- ( 4-nitrophenyl) ethyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (2-nitrophenyl) propyl] -4,4 -Dimethyl-3-oxopyrazolidine, (S) -1- [1 (Trifluoromethyl) -3- (3-nitrophenyl) propyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (4- Nitrophenyl) propyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -4- (2-nitrophenyl) butyl] -4,4-dimethyl -3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -4- (3-nitrophenyl) butyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -4- (4-nitrophenyl) butyl] -4,4-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -5- (2-Nitrophenyl) butyl]- , 4-Dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -5- (3-nitrophenyl) butyl] -4,4-dimethyl-3-oxopyrazolidine (S) -1- [1- (trifluoromethyl) -5- (4-nitrophenyl) butyl] -4,4-dimethyl-3-oxopyrazolidine and the like.

本発明の一般式(1)で表される光学活性5,5−ジメチル−3−オキソピペラゾリジン誘導体で、Rがメチル基、エチル基、炭素数3〜10の直鎖、分岐若しくは環式のアルキル基であるものとしては、具体的には例えば、(S)−1−(1,1,1−トリフルオロ−2−プロピル)−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−(1,1,1−トリフルオロ−2−ブチル)−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−(1,1,1−トリフルオロ−2−ペンチル)−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−(1,1,1−トリフルオロ−3−メチル−2−ブチル)−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−(1,1,1−トリフルオロ−2−ヘキシル)−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−(1,1,1−トリフルオロ−3,3−ジメチル−2−ブチレン)−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−(1,1,1−トリフルオロ−2−ヘプチル)−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−(1,1,1−トリフルオロ−2−オクチル)−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−(1,1,1−トリフルオロ−3−シクロヘキシル−2−エチル)−5,5−ジメチル−3−オキソピラゾリン、(S)−1−(1,1,1−トリフルオロ−2−ノニル)−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−(1,1,1−トリフルオロ−2−デシル)−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−(1,1,1−トリフルオロ−2−ウンデシル)−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−(1,1,1−トリフルオロ−2−ドデシル)−3−オキソピラゾリジン等を挙げることができる。 An optically active 5,5-dimethyl-3-oxopiperazolidine derivative represented by the general formula (1) of the present invention, wherein R 3 is a methyl group, an ethyl group, a linear, branched or ring having 3 to 10 carbon atoms. Specific examples of the alkyl group of the formula include (S) -1- (1,1,1-trifluoro-2-propyl) -5,5-dimethyl-3-oxopyrazolidine, (S) -1- (1,1,1-trifluoro-2-butyl) -5,5-dimethyl-3-oxopyrazolidine, (S) -1- (1,1,1-trifluoro- 2-pentyl) -5,5-dimethyl-3-oxopyrazolidine, (S) -1- (1,1,1-trifluoro-3-methyl-2-butyl) -5,5-dimethyl-3 -Oxopyrazolidine, (S) -1- (1,1,1-trifluoro-2-hexyl) -5,5-dimethyl Ru-3-oxopyrazolidine, (S) -1- (1,1,1-trifluoro-3,3-dimethyl-2-butylene) -5,5-dimethyl-3-oxopyrazolidine, ( S) -1- (1,1,1-trifluoro-2-heptyl) -5,5-dimethyl-3-oxopyrazolidine, (S) -1- (1,1,1-trifluoro-2) -Octyl) -5,5-dimethyl-3-oxopyrazolidine, (S) -1- (1,1,1-trifluoro-3-cyclohexyl-2-ethyl) -5,5-dimethyl-3- Oxopyrazoline, (S) -1- (1,1,1-trifluoro-2-nonyl) -5,5-dimethyl-3-oxopyrazolidine, (S) -1- (1,1,1-tri Fluoro-2-decyl) -5,5-dimethyl-3-oxopyrazolidine, (S) -1- (1,1,1-to Fluoro-2-undecyl) -5,5-dimethyl-3-oxopyrazolidine, (S) -1- (1,1,1-trifluoro-2-dodecyl) -3-oxopyrazolidine and the like be able to.

本発明の一般式(1)で表される光学活性5,5−ジメチル−3−オキソピペラゾリジン誘導体で、Rが置換基を有しても良いフェニル基であるものとしては、具体的には例えば、(S)−1−(2,2,2−トリフルオロ−1−フェニル−1−エチル)−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−メチルフェニル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−メチルフェニル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−メチルフェニル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−エチルフェニル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−エチルフェニル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−エチルフェニル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−n−プロピルフェニル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−n−プロピルフェニル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−プロピルフェニル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−iso−プロピルフェニル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−iso−プロピルフェニル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−iso−プロピルフェニル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−n−ブチルフェニル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−n−ブチルフェニル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−ブチルフェニル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−iso−ブチルフェニル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−iso−ブチルフェニル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−iso−ブチルフェニル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−tert−ブチルフェニル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−tert−ブチルフェニル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−tert−ブチルフェニル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−ペンチルフェニル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−ヘキシルフェニル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−ヘプチルフェニル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−オクチルフェニル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−ノニルフェニル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−デシルフェニル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−メトキシフェニル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−メトキシフェニル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−メトキシフェニル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−エトキシフェニル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−エトキシフェニル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−エトキシフェニル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−n−プロポキシフェニル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−n−プロポキシフェニル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−プロポキシフェニル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−iso−プロポキシフェニル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−iso−プロポキシフェニル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−iso−プロポキシフェニル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−n−ブトキシフェニル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−n−ブトキシフェニル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−ブトキシフェニル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−iso−ブトキシフェニル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−iso−ブトキシフェニル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−iso−ブトキシフェニル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−tert−ブトキシフェニル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−tert−ブトキシフェニル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−tert−ブトキシフェニル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−ペントキシフェニル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−ヘキシルオキシフェニル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−ヘプチルオキシフェニル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−オクチルオキシフェニル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−ノニルオキシフェニル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−デシルオキシフェニル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−フルオロフェニル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−フルオロフェニル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−フルオロフェニル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−クロロフェニル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−クロロフェニル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−クロロフェニル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−ブロモフェニル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−ブロモフェニル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−ブロモフェニル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−シアノフェニル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−シアノフェニル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−シアノフェニル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−ニトロフェニル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−ニトロフェニル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−ニトロフェニル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン等を挙げることができる。 Specific examples of the optically active 5,5-dimethyl-3-oxopiperazolidine derivative represented by the general formula (1) of the present invention, in which R 3 is a phenyl group which may have a substituent, include: For example, (S) -1- (2,2,2-trifluoro-1-phenyl-1-ethyl) -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2 , 2,2-trifluoro-1- (2-methylphenyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro -1- (3-methylphenyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-methyl) Phenyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2 , 2-trifluoro-1- (2-ethylphenyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1 -(3-Ethylphenyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-ethylphenyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (2-n-propylphenyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (3-n-propylphenyl) -1-ethyl] -5,5- Dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-n- (Lopylphenyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (2-iso-propylphenyl) -1- Ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (3-iso-propylphenyl) -1-ethyl] -5, 5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-iso-propylphenyl) -1-ethyl] -5,5-dimethyl-3 -Oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (2-n-butylphenyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine , (S) -1- [2,2,2-trifluoro-1- (3-n-butyl Enyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-n-butylphenyl) -1- Ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (2-iso-butylphenyl) -1-ethyl] -5, 5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (3-iso-butylphenyl) -1-ethyl] -5,5-dimethyl-3 -Oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-iso-butylphenyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine , (S) -1- [2,2,2-trifluoro-1- (2-tert-butylphenyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (3-tert-butylphenyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-tert-butylphenyl) -1-ethyl] -5,5- Dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-n-pentylphenyl) -1-ethyl] -5,5-dimethyl-3-oxo Pyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-n-hexylphenyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, ( S) -1- [2,2,2-trifluoro-1- (4-n-heptylphenyl) -1-e L] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-n-octylphenyl) -1-ethyl] -5, 5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-n-nonylphenyl) -1-ethyl] -5,5-dimethyl-3 -Oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-n-decylphenyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine (S) -1- [2,2,2-trifluoro-1- (2-methoxyphenyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (3-methoxyphenyl) -1-ethyl] -5,5-dimethyl-3 Oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-methoxyphenyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S ) -1- [2,2,2-trifluoro-1- (2-ethoxyphenyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2, 2,2-trifluoro-1- (3-ethoxyphenyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro- 1- (4-Ethoxyphenyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (2-n- (Propoxyphenyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1 -[2,2,2-trifluoro-1- (3-n-propoxyphenyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2 , 2-trifluoro-1- (4-n-propoxyphenyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro -1- (2-iso-propoxyphenyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (3 -Iso-propoxyphenyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-iso-propoxyphenyl) ) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S -1- [2,2,2-trifluoro-1- (2-n-butoxyphenyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2 , 2,2-trifluoro-1- (3-n-butoxyphenyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2- Trifluoro-1- (4-n-butoxyphenyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (2-iso-butoxyphenyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (3-iso- Butoxyphenyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- 2,2,2-trifluoro-1- (4-iso-butoxyphenyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2 -Trifluoro-1- (2-tert-butoxyphenyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1 -(3-tert-butoxyphenyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-tert -Butoxyphenyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-n-pentoxyphenyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-n-hexyloxyphenyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [ 2,2,2-trifluoro-1- (4-n-heptyloxyphenyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2, 2-trifluoro-1- (4-n-octyloxyphenyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro -1- (4-n-nonyloxyphenyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- ( 4-n-decyloxyphenyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolid (S) -1- [2,2,2-trifluoro-1- (2-fluorophenyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (3-fluorophenyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2- Trifluoro-1- (4-fluorophenyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (2 -Chlorophenyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (3-chlorophenyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro -1- (4-chlorophenyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (2-bromophenyl) ) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (3-bromophenyl) -1-ethyl]- 5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-bromophenyl) -1-ethyl] -5,5-dimethyl-3 -Oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (2-cyanophenyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, ( S) -1- [2,2,2-trifluoro-1- (3-cyanophenyl) -1-ethyl] -5 , 5-Dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-cyanophenyl) -1-ethyl] -5,5-dimethyl-3- Oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (2-nitrophenyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S ) -1- [2,2,2-trifluoro-1- (3-nitrophenyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2, 2,2-trifluoro-1- (4-nitrophenyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine and the like can be mentioned.

本発明の一般式(1)で表される光学活性5,5−ジメチル−3−オキソピペラゾリジン誘導体で、Rが置換基を有しても良い1−ナフチル基であるものとしては、具体的には例えば、(S)−1−[2,2,2−トリフルオロ−1−(1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−メチル−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−メチル−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−メチル−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−メチル−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−メチル−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−メチル−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−メチル−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−エチル−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−エチル−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−エチル−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−エチル−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−エチル−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−エチル−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−エチル−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−n−プロピル−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−n−プロピル−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−プロピル−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−n−プロピル−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−プロピル−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−n−プロピル−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−プロピル−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−iso−プロピル−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−iso−プロピル−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−iso−プロピル−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−iso−プロピル−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−iso−プロピル−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−iso−プロピル−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−iso−プロピル−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−n−ブチル−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−n−ブチル−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−ブチル−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−n−ブチル−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−ブチル−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−n−ブチル−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−ブチル−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−iso−ブチル−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−iso−ブチル−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−iso−ブチル−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−iso−ブチル−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−iso−ブチル−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−iso−ブチル−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−iso−ブチル−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−tert−ブチル−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−tert−ブチル−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−tert−ブチル−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−tert−ブチル−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−tert−ブチル−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−tert−ブチル−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−tert−ブチル−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−n−ペンチル−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−ペンチル−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−ペンチル−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−ペンチル−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−n−ヘキシル−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−ヘキシル−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−ヘキシル−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−ヘキシル−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−n−ヘプチル−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−ヘプチル−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−ヘプチル−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−ヘプチル−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−n−オクチル−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−オクチル−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−オクチル−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−オクチル−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−n−ノニル−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−ノニル−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−ノニル−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−ノニル−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−n−デシル−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−デシル−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−デシル−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−デシル−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−メトキシ
−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−メトキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−メトキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−メトキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−メトキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−メトキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−メトキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−エトキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−エトキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−エトキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−エトキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−エトキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−エトキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−エトキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−n−プロポキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−n−プロポキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−プロポキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−n−プロポキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−プロポキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−n−プロポキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−プロポキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−iso−プロポキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−iso−プロポキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−iso−プロポキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−iso−プロポキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−iso−プロポキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−iso−プロポキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−iso−プロポキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−n−ブトキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−n−ブトキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−ブトキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−n−ブトキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−ブトキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−n−ブトキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−ブトキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−iso−ブトキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−iso−ブトキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−iso−ブトキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−iso−ブトキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−iso−ブトキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−iso−ブトキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−iso−ブトキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−tert−ブトキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−tert−ブトキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−tert−ブトキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−tert−ブトキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−tert−ブトキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−tert−ブトキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−tert−ブトキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−n−ペントキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−ペントキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−ペントキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−ペントキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−n−ヘキシルオキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−ヘキシルオキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−ヘキシルオキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−ヘキシルオキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−n−ヘプチルオキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−ヘプチルオキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−ヘプチルオキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−ヘプチルオキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−n−オクチルオキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−オクチルオキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−オクチルオキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−オクチルオキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−n−ノニルオキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−ノニルオキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−ノニルオキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−ノニルオキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−n−デシルオキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−デシルオキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−デシルオキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−デシルオキシ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−フルオロ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−フルオロ
−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−フルオロ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−フルオロ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−フルオロ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−フルオロ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−フルオロ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−クロロ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−クロロ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−クロロ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−クロロ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−クロロ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−クロロ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−クロロ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−ブロモ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−ブロモ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−ブロモ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−ブロモ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−ブロモ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−ブロモ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−ブロモ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−シアノ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−シアノ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−シアノ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−シアノ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−シアノ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−シアノ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−シアノ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−ニトロ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−ニトロ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−ニトロ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−ニトロ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−ニトロ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−ニトロ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−ニトロ−1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン等を挙げることができる。
The optically active 5,5-dimethyl-3-oxopiperazolidine derivative represented by the general formula (1) of the present invention, R 3 Specific examples of the 1-naphthyl group which may have a substituent include (S) -1- [2,2,2-trifluoro-1- (1-naphthyl) -1 -Ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (2-methyl-1-naphthyl) -1-ethyl]- 5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (3-methyl-1-naphthyl) -1-ethyl] -5,5- Dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-methyl-1-naphthyl) -1-ethyl] -5,5-dimethyl-3- Oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (5-methyl-1-naphthyl) -1-ethyl -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (6-methyl-1-naphthyl) -1-ethyl] -5,5 -Dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (7-methyl-1-naphthyl) -1-ethyl] -5,5-dimethyl-3 -Oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (8-methyl-1-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazo Lysine, (S) -1- [2,2,2-trifluoro-1- (2-ethyl-1-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S ) -1- [2,2,2-trifluoro-1- (3-ethyl-1-naphthyl) -1-ethyl] -5,5-dimethyl Ru-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-ethyl-1-naphthyl) -1-ethyl] -5,5-dimethyl-3- Oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (5-ethyl-1-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine (S) -1- [2,2,2-trifluoro-1- (6-ethyl-1-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (7-ethyl-1-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [ 2,2,2-trifluoro-1- (8-ethyl-1-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopi Lazolidine, (S) -1- [2,2,2-trifluoro-1- (2-n-propyl-1-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (3-n-propyl-1-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S ) -1- [2,2,2-trifluoro-1- (4-n-propyl-1-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S)- 1- [2,2,2-trifluoro-1- (5-n-propyl-1-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (6-n-propyl-1-naphthyl) -1-ethyl] -5,5-dimethyl 3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (7-n-propyl-1-naphthyl) -1-ethyl] -5,5-dimethyl-3- Oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (8-n-propyl-1-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyra Zolidine, (S) -1- [2,2,2-trifluoro-1- (2-iso-propyl-1-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine (S) -1- [2,2,2-trifluoro-1- (3-iso-propyl-1-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, S) -1- [2,2,2-trifluoro-1- (4-iso-propyl-1-naphthyl) -1- Til] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (5-iso-propyl-1-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (6-iso-propyl-1-naphthyl) -1-ethyl] -5 , 5-Dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (7-iso-propyl-1-naphthyl) -1-ethyl] -5,5 -Dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (8-iso-propyl-1-naphthyl) -1-ethyl] -5,5-dimethyl -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (2-n-butyl) Til-1-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (3-n-butyl-) 1-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-n-butyl-1- Naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (5-n-butyl-1-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (6-n-butyl-1-naphthyl) -1 -Ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (7-n Butyl-1-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (8-n-butyl-) 1-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (2-iso-butyl-1- Naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (3-iso-butyl-1-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-iso-butyl-1-naphthyl) -1 -Ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro -1- (5-iso-butyl-1-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1 -(6-Iso-butyl-1-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- ( 7-iso-butyl-1-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (8- iso-butyl-1-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (2-tert- Butyl-1-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (3-tert-butyl-1-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2 , 2,2-trifluoro-1- (4-tert-butyl-1-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2 , 2-trifluoro-1- (5-tert-butyl-1-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2 -Trifluoro-1- (6-tert-butyl-1-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-tri Fluoro-1- (7-tert-butyl-1-naphthyl) -1-ethyl] -5,5-dimethyl-3 Oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (8-tert-butyl-1-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyra Zolidine, (S) -1- [2,2,2-trifluoro-1- (2-n-pentyl-1-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine (S) -1- [2,2,2-trifluoro-1- (4-n-pentyl-1-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, S) -1- [2,2,2-trifluoro-1- (6-n-pentyl-1-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (8-n-pentyl-1-naphthyl) -1-ethyl] -5 5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (2-n-hexyl-1-naphthyl) -1-ethyl] -5,5- Dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-n-hexyl-1-naphthyl) -1-ethyl] -5,5-dimethyl- 3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (6-n-hexyl-1-naphthyl) -1-ethyl] -5,5-dimethyl-3- Oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (8-n-hexyl-1-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyra Zolidine, (S) -1- [2,2,2-trifluoro-1- (2-n-heptyl-1-naphthyl) -1- Ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-n-heptyl-1-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (6-n-heptyl-1-naphthyl) -1-ethyl] -5 , 5-Dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (8-n-heptyl-1-naphthyl) -1-ethyl] -5,5 -Dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (2-n-octyl-1-naphthyl) -1-ethyl] -5,5-dimethyl -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-n-octyl-1-na Til) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (6-n-octyl-1-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (8-n-octyl-1-naphthyl) -1 -Ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (2-n-nonyl-1-naphthyl) -1-ethyl ] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-n-nonyl-1-naphthyl) -1-ethyl]- 5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (6-n-nonyl) 1-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (8-n-nonyl-1-) Naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (2-n-decyl-1-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-n-decyl-1-naphthyl) -1 -Ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (6-n-decyl-1-naphthyl) -1-ethyl ] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (8-n-dec Ru-1-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (2-methoxy)
-1-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (3-methoxy-1-naphthyl) ) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-methoxy-1-naphthyl) -1- Ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (5-methoxy-1-naphthyl) -1-ethyl] -5 , 5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (6-methoxy-1-naphthyl) -1-ethyl] -5,5-dimethyl -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (7-methoxy-1- Butyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (8-methoxy-1-naphthyl) -1 -Ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (2-ethoxy-1-naphthyl) -1-ethyl]- 5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (3-ethoxy-1-naphthyl) -1-ethyl] -5,5- Dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-ethoxy-1-naphthyl) -1-ethyl] -5,5-dimethyl-3- Oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (5-ethoxy-1-naphthy) ) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (6-ethoxy-1-naphthyl) -1- Ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (7-ethoxy-1-naphthyl) -1-ethyl] -5 , 5-Dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (8-ethoxy-1-naphthyl) -1-ethyl] -5,5-dimethyl -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (2-n-propoxy-1-naphthyl) -1-ethyl] -5,5-dimethyl-3 -Oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (3-n-propoxy-1-na Butyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-n-propoxy-1-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (5-n-propoxy-1-naphthyl) -1 -Ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (6-n-propoxy-1-naphthyl) -1-ethyl ] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (7-n-propoxy-1-naphthyl) -1-ethyl]- 5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (8 n-propoxy-1-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (2-iso- Propoxy-1-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (3-iso-propoxy-) 1-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-iso-propoxy-1- Naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (5-iso-propoxy-1-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S)- -[2,2,2-trifluoro-1- (6-iso-propoxy-1-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [ 2,2,2-trifluoro-1- (7-iso-propoxy-1-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2, 2,2-trifluoro-1- (8-iso-propoxy-1-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2, 2-trifluoro-1- (2-n-butoxy-1-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2- Trifluoro-1- (3-n-butoxy-1-naphthyl) -1-ethyl] -5,5-dimethyl-3 -Oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-n-butoxy-1-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxo Pyrazolidine, (S) -1- [2,2,2-trifluoro-1- (5-n-butoxy-1-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazo Lysine, (S) -1- [2,2,2-trifluoro-1- (6-n-butoxy-1-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (7-n-butoxy-1-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S ) -1- [2,2,2-trifluoro-1- (8-n-butoxy-1-naphthyl) -1-ethyl] -5,5 Dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (2-iso-butoxy-1-naphthyl) -1-ethyl] -5,5-dimethyl- 3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (3-iso-butoxy-1-naphthyl) -1-ethyl] -5,5-dimethyl-3- Oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-iso-butoxy-1-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyra Zolidine, (S) -1- [2,2,2-trifluoro-1- (5-iso-butoxy-1-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine , (S) -1- [2,2,2-trifluoro-1- (6-iso-butoxy-1) Naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (7-iso-butoxy-1-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (8-iso-butoxy-1-naphthyl) -1 -Ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (2-tert-butoxy-1-naphthyl) -1-ethyl ] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (3-tert-butoxy-1-naphthyl) -1-ethyl]- 5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro Oro-1- (4-tert-butoxy-1-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro- 1- (5-tert-butoxy-1-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (6-tert-butoxy-1-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (7 -Tert-butoxy-1-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (8-tert -Butoxy-1-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyra Lysine, (S) -1- [2,2,2-trifluoro-1- (2-n-pentoxy-1-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-n-pentoxy-1-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S ) -1- [2,2,2-trifluoro-1- (6-n-pentoxy-1-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S)- 1- [2,2,2-trifluoro-1- (8-n-pentoxy-1-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (2-n-hexyloxy-1-naphthyl) -1-ethyl] -5 -Dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-n-hexyloxy-1-naphthyl) -1-ethyl] -5,5- Dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (6-n-hexyloxy-1-naphthyl) -1-ethyl] -5,5-dimethyl -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (8-n-hexyloxy-1-naphthyl) -1-ethyl] -5,5-dimethyl- 3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (2-n-heptyloxy-1-naphthyl) -1-ethyl] -5,5-dimethyl-3 -Oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-n-heptyl) Oxy-1-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (6-n-heptyloxy) -1-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (8-n-heptyloxy-) 1-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (2-n-octyloxy-1) -Naphtyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-n-octyloxy-1- Naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2, , 2-trifluoro-1- (6-n-octyloxy-1-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2, 2-trifluoro-1- (8-n-octyloxy-1-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2 -Trifluoro-1- (2-n-nonyloxy-1-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-tri Fluoro-1- (4-n-nonyloxy-1-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro- 1- (6-n-nonyloxy-1-naphthyl) -1-ethyl] -5,5-dimethyl-3- Xopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (8-n-nonyloxy-1-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (2-n-decyloxy-1-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S ) -1- [2,2,2-trifluoro-1- (4-n-decyloxy-1-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S)- 1- [2,2,2-trifluoro-1- (6-n-decyloxy-1-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (8-n-decyloxy-1-naphthyl) -1- Ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (2-fluoro-1-naphthyl) -1-ethyl] -5 , 5-Dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (3-fluoro
-1-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-fluoro-1-naphthyl) ) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (5-fluoro-1-naphthyl) -1- Ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (6-fluoro-1-naphthyl) -1-ethyl] -5 , 5-Dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (7-fluoro-1-naphthyl) -1-ethyl] -5,5-dimethyl -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (8-fluoro-1- Butyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (2-chloro-1-naphthyl) -1 -Ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (3-chloro-1-naphthyl) -1-ethyl]- 5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-chloro-1-naphthyl) -1-ethyl] -5,5- Dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (5-chloro-1-naphthyl) -1-ethyl] -5,5-dimethyl-3- Oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (6-chloro-1-naphthyl) -1- Til] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (7-chloro-1-naphthyl) -1-ethyl] -5 , 5-Dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (8-chloro-1-naphthyl) -1-ethyl] -5,5-dimethyl -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (2-bromo-1-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxo Pyrazolidine, (S) -1- [2,2,2-trifluoro-1- (3-bromo-1-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-bromo-1-naphthyl) -1-ethyl] -5,5- Dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (5-bromo-1-naphthyl) -1-ethyl] -5,5-dimethyl-3- Oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (6-bromo-1-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine (S) -1- [2,2,2-trifluoro-1- (7-bromo-1-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (8-bromo-1-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [ 2,2,2-trifluoro-1- (2-cyano-1-naphthyl) -1-ethyl] -5,5-dimethyl-3-o Sopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (3-cyano-1-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S ) -1- [2,2,2-trifluoro-1- (4-cyano-1-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (5-cyano-1-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2 , 2-trifluoro-1- (6-cyano-1-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-tri Fluoro-1- (7-cyano-1-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine (S) -1- [2,2,2-trifluoro-1- (8-cyano-1-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S)- 1- [2,2,2-trifluoro-1- (2-nitro-1-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2 , 2,2-trifluoro-1- (3-nitro-1-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2 -Trifluoro-1- (4-nitro-1-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro- 1- (5-nitro-1-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2 , 2,2-trifluoro-1- (6-nitro-1-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2 -Trifluoro-1- (7-nitro-1-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro- And 1- (8-nitro-1-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine.

本発明の一般式(1)で表される光学活性5,5−ジメチル−3−オキソピペラゾリジン誘導体で、Rが置換基を有しても良い2−ナフチル基であるものとしては、具体的には例えば、(S)−1−[2,2,2−トリフルオロ−1−(2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−メチル−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−メチル−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−メチル−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−メチル−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−メチル−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−メチル−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−メチル−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−エチル−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−エチル−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−エチル−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−エチル−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−エチル−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−エチル−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−エチル−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−n−プロピル−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−n−プロピル−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−n−プロピル−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−プロピル−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−n−プロピル−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−プロピル−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−n−プロピル−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−プロピル−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−iso−プロピル−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−iso−プロピル−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−iso−プロピル−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−iso−プロピル−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−iso−プロピル−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−iso−プロピル−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−iso−プロピル−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−n−ブチル−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−n−ブチル−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−ブチル−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−n−ブチル−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−ブチル−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−n−ブチル−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−ブチル−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−iso−ブチル−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−iso−ブチル−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−iso−ブチル−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−iso−ブチル−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−iso−ブチル−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−iso−ブチル−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−iso−ブチル−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−iso−ブチル−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−tert−ブチル−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(2−tert−ブチル−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−tert−ブチル−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−tert−ブチル−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−tert−ブチル−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−tert−ブチル−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−tert−ブチル−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−tert−ブチル−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−n−ペンチル−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−ペンチル−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−ペンチル−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−ペンチル−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−n−ヘキシル−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−ヘキシル−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−ヘキシル−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−ヘキシル−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−n−ヘプチル−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−ヘプチル−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−ヘプチル−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−ヘプチル−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−n−オクチル−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−オクチル−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−オクチル−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−オクチル−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−n−ノニル−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−ノニル−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−ノニル−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−ノニル−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−n−デシル−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(
4−n−デシル−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−デシル−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−デシル−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−メトキシ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−メトキシ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−メトキシ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−メトキシ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−メトキシ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−メトキシ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−メトキシ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−エトキシ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−エトキシ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−エトキシ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−エトキシ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−エトキシ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−エトキシ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−エトキシ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−n−プロポキ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−n−プロポキ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−プロポキ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−n−プロポキ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−プロポキ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−n−プロポキ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−プロポキ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−iso−プロポキ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−iso−プロポキ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−iso−プロポキ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−iso−プロポキ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−iso−プロポキ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−iso−プロポキ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−iso−プロポキ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−n−ブトキシ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−n−ブトキシ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−ブトキシ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−n−ブトキシ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−ブトキシ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−n−ブトキシ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−ブトキシ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−iso−ブトキシ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−iso−ブトキシ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−iso−ブトキシ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−iso−ブトキシ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−iso−ブトキシ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−iso−ブトキシ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−iso−ブトキシ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−tert−ブトキシ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−tert−ブトキシ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−tert−ブトキシ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−tert−ブトキシ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−tert−ブトキシ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−tert−ブトキシ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−tert−ブトキシ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−n−ペントキシ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−ペントキシ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−ペントキシ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−ペントキシ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−n−ヘキシルオキシ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−ヘキシルオキシ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−ヘキシルオキシ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−ヘキシルオキシ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−n−ヘプチルオキシ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−ヘプチルオキシ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−ヘプチルオキシ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−ヘプチルオキシ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−n−オクチルオキシ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−オクチルオキシ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−オクチルオキシ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−オクチルオキシ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−n−ノニルオキシ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−ノニルオキシ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−ノニルオキシ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−ノニルオキシ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−n−デシルオキシ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−n−デシルオキシ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−n−デシルオキシ−2−ナフチル)−
1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−n−デシルオキシ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−フルオロ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−フルオロ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−フルオロ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−フルオロ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−フルオロ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−フルオロ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−フルオロ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−クロロ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−クロロ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−クロロ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−クロロ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−クロロ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−クロロ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−クロロ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−ブロモ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−ブロモ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−ブロモ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−ブロモ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−ブロモ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−ブロモ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−ブロモ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−シアノ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−シアノ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−シアノ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−シアノ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−シアノ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−シアノ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−シアノ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(1−ニトロ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(3−ニトロ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(4−ニトロ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(5−ニトロ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(6−ニトロ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(7−ニトロ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[2,2,2−トリフルオロ−1−(8−ニトロ−2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン等を挙げることができる。
The optically active 5,5-dimethyl-3-oxopiperazolidine derivative represented by the general formula (1) of the present invention, R 3 Specific examples of the 2-naphthyl group that may have a substituent include (S) -1- [2,2,2-trifluoro-1- (2-naphthyl) -1 -Ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (1-methyl-2-naphthyl) -1-ethyl]- 5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (3-methyl-2-naphthyl) -1-ethyl] -5,5- Dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-methyl-2-naphthyl) -1-ethyl] -5,5-dimethyl-3- Oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (5-methyl-2-naphthyl) -1-ethyl -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (6-methyl-2-naphthyl) -1-ethyl] -5,5 -Dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (7-methyl-2-naphthyl) -1-ethyl] -5,5-dimethyl-3 -Oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (8-methyl-2-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazo Lysine, (S) -1- [2,2,2-trifluoro-1- (1-ethyl-2-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S ) -1- [2,2,2-trifluoro-1- (3-ethyl-2-naphthyl) -1-ethyl] -5,5-dimethyl Ru-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-ethyl-2-naphthyl) -1-ethyl] -5,5-dimethyl-3- Oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (5-ethyl-2-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine (S) -1- [2,2,2-trifluoro-1- (6-ethyl-2-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (7-ethyl-2-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [ 2,2,2-trifluoro-1- (8-ethyl-2-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopi Lazolidine, (S) -1- [2,2,2-trifluoro-1- (1-n-propyl-2-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (2-n-propyl-2-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S ) -1- [2,2,2-trifluoro-1- (3-n-propyl-2-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S)- 1- [2,2,2-trifluoro-1- (4-n-propyl-2-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (5-n-propyl-2-naphthyl) -1-ethyl] -5,5-dimethyl 3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (6-n-propyl-2-naphthyl) -1-ethyl] -5,5-dimethyl-3- Oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (7-n-propyl-2-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyra Zolidine, (S) -1- [2,2,2-trifluoro-1- (8-n-propyl-2-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine (S) -1- [2,2,2-trifluoro-1- (1-iso-propyl-2-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, S) -1- [2,2,2-trifluoro-1- (3-iso-propyl-2-naphthyl) -1-eth ] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-iso-propyl-2-naphthyl) -1-ethyl]- 5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (5-iso-propyl-2-naphthyl) -1-ethyl] -5, 5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (6-iso-propyl-2-naphthyl) -1-ethyl] -5,5- Dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (7-iso-propyl-2-naphthyl) -1-ethyl] -5,5-dimethyl- 3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (8-iso-propyl) (Lopyl-2-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (1-n-butyl-) 2-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (3-n-butyl-2- Naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-n-butyl-2-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (5-n-butyl-2-naphthyl) -1 -Ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (6- -Butyl-2-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (7-n-butyl) -2-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (8-n-butyl-2) -Naphtyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (1-iso-butyl-2-naphthyl) ) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (2-iso-butyl-2-naphthyl)- 1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro 1- (3-Iso-butyl-2-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-Iso-butyl-2-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (5 -Iso-butyl-2-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (6-iso -Butyl-2-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (7-iso-butyl) -2-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2 , 2,2-Trifluoro-1- (8-iso-butyl-2-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2 , 2-trifluoro-1- (1-tert-butyl-2-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2 -Trifluoro-1- (2-tert-butyl-2-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-tri Fluoro-1- (3-tert-butyl-2-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro- 1- (4-tert-butyl-2-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxy Pyrazolidine, (S) -1- [2,2,2-trifluoro-1- (5-tert-butyl-2-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (6-tert-butyl-2-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S ) -1- [2,2,2-trifluoro-1- (7-tert-butyl-2-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S)- 1- [2,2,2-trifluoro-1- (8-tert-butyl-2-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (1-n-pentyl-2-naphthyl) -1-ethyl -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-n-pentyl-2-naphthyl) -1-ethyl] -5 , 5-Dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (6-n-pentyl-2-naphthyl) -1-ethyl] -5,5 -Dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (8-n-pentyl-2-naphthyl) -1-ethyl] -5,5-dimethyl -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (1-n-hexyl-2-naphthyl) -1-ethyl] -5,5-dimethyl-3 -Oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-n-hexyl-2-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (6-n-hexyl-2-naphthyl) -1 -Ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (8-n-hexyl-2-naphthyl) -1-ethyl ] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (1-n-heptyl-2-naphthyl) -1-ethyl]- 5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-n-heptyl-2-naphthyl) -1-ethyl] -5, 5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (6-n-heptyl- -Naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (8-n-heptyl-2-naphthyl) ) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (1-n-octyl-2-naphthyl)- 1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-n-octyl-2-naphthyl) -1- Ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (6-n-octyl-2-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (8- -Octyl-2-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (1-n-nonyl) -2-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-n-nonyl-2) -Naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (6-n-nonyl-2-naphthyl) ) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (8-n-nonyl-2-naphthyl)- 1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- ( 1-n-decyl-2-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (
4-n-decyl-2-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (6- n-decyl-2-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (8-n- Decyl-2-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (1-methoxy-2-) Naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (3-methoxy-2-naphthyl) -1 -Ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- ( -Methoxy-2-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (5-methoxy-2) -Naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (6-methoxy-2-naphthyl)- 1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (7-methoxy-2-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (8-methoxy-2-naphthyl) -1-ethyl] -5,5 -Dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (1-e Xyl-2-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (3-ethoxy-2- Naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-ethoxy-2-naphthyl) -1 -Ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (5-ethoxy-2-naphthyl) -1-ethyl]- 5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (6-ethoxy-2-naphthyl) -1-ethyl] -5,5- Dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (7-ethoxy- 2-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (8-ethoxy-2-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (1-n-propoxy-2-naphthyl) -1 -Ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (3-n-propoxy-2-naphthyl) -1-ethyl ] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-n-propoxy-2-naphthyl) -1-ethyl]- 5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (5-n- (Lopoxy-2-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (6-n-propoxy) 2-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (7-n-propoxy-2-one) Naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (8-n-propoxy-2-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (1-iso-propoxy-2-naphthyl) -1 -Ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro -1- (3-iso-propoxy-2-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1 -(4-Iso-propoxy-2-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- ( 5-iso-propoxy-2-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (6- iso-propoxy-2-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (7-iso- Propoxy-2-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S ) -1- [2,2,2-trifluoro-1- (8-iso-propoxy-2-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S)- 1- [2,2,2-trifluoro-1- (1-n-butoxy-2-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (3-n-butoxy-2-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2 , 2,2-trifluoro-1- (4-n-butoxy-2-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2 , 2-Trifluoro-1- (5-n-butoxy-2-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxo Lazolidine, (S) -1- [2,2,2-trifluoro-1- (6-n-butoxy-2-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (7-n-butoxy-2-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S ) -1- [2,2,2-trifluoro-1- (8-n-butoxy-2-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S)- 1- [2,2,2-trifluoro-1- (1-iso-butoxy-2-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (3-iso-butoxy-2-naphthyl) -1-ethyl] -5,5 Dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-iso-butoxy-2-naphthyl) -1-ethyl] -5,5-dimethyl- 3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (5-iso-butoxy-2-naphthyl) -1-ethyl] -5,5-dimethyl-3- Oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (6-iso-butoxy-2-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyra Zolidine, (S) -1- [2,2,2-trifluoro-1- (7-iso-butoxy-2-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine , (S) -1- [2,2,2-trifluoro-1- (8-iso-butoxy-2- Naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (1-tert-butoxy-2-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (3-tert-butoxy-2-naphthyl) -1 -Ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-tert-butoxy-2-naphthyl) -1-ethyl ] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (5-tert-butoxy-2-naphthyl) -1-ethyl]- 5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-tri Fluoro-1- (6-tert-butoxy-2-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro- 1- (7-tert-butoxy-2-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (8-tert-butoxy-2-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (1 -N-pentoxy-2-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-n -Pentoxy-2-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazoli (S) -1- [2,2,2-trifluoro-1- (6-n-pentoxy-2-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (8-n-pentoxy-2-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S ) -1- [2,2,2-trifluoro-1- (1-n-hexyloxy-2-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-n-hexyloxy-2-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S)- 1- [2,2,2-trifluoro-1- (6-n-hexyloxy-2-naphthyl) -1-ethyl] -5 , 5-Dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (8-n-hexyloxy-2-naphthyl) -1-ethyl] -5, 5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (1-n-heptyloxy-2-naphthyl) -1-ethyl] -5,5 -Dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-n-heptyloxy-2-naphthyl) -1-ethyl] -5,5- Dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (6-n-heptyloxy-2-naphthyl) -1-ethyl] -5,5-dimethyl -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (8-n-hept Ruoxy-2-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (1-n-octyloxy) -2-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-n-octyloxy-) 2-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (6-n-octyloxy-2) -Naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (8-n-octyloxy-2-) Naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [ , 2,2-trifluoro-1- (1-n-nonyloxy-2-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2 , 2-trifluoro-1- (4-n-nonyloxy-2-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2 -Trifluoro-1- (6-n-nonyloxy-2-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-tri Fluoro-1- (8-n-nonyloxy-2-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro- 1- (1-n-decyloxy-2-naphthyl) -1-ethyl] -5,5-dimethyl-3-o Xopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-n-decyloxy-2-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (6-n-decyloxy-2-naphthyl)-
1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (8-n-decyloxy-2-naphthyl) -1- Ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (1-fluoro-2-naphthyl) -1-ethyl] -5 , 5-Dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (3-fluoro-2-naphthyl) -1-ethyl] -5,5-dimethyl -3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-fluoro-2-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxo Pyrazolidine, (S) -1- [2,2,2-trifluoro-1- (5-fluoro-2-naphthyl) 1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (6-fluoro-2-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (7-fluoro-2-naphthyl) -1-ethyl] -5,5 -Dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (8-fluoro-2-naphthyl) -1-ethyl] -5,5-dimethyl-3 -Oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (1-chloro-2-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazo Lysine, (S) -1- [2,2,2-trifluoro-1- (3-chloro-2-naphthyl) -1-ethyl ] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (4-chloro-2-naphthyl) -1-ethyl] -5, 5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (5-chloro-2-naphthyl) -1-ethyl] -5,5-dimethyl- 3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (6-chloro-2-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyra Zolidine, (S) -1- [2,2,2-trifluoro-1- (7-chloro-2-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, ( S) -1- [2,2,2-trifluoro-1- (8-chloro-2-naphthyl) -1-ethyl] -5,5-dimethyl Tyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (1-bromo-2-naphthyl) -1-ethyl] -5,5-dimethyl-3- Oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (3-bromo-2-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine (S) -1- [2,2,2-trifluoro-1- (4-bromo-2-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (5-bromo-2-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [ 2,2,2-trifluoro-1- (6-bromo-2-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxo Lazolidine, (S) -1- [2,2,2-trifluoro-1- (7-bromo-2-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S ) -1- [2,2,2-trifluoro-1- (8-bromo-2-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (1-cyano-2-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2 , 2-trifluoro-1- (3-cyano-2-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-tri Fluoro-1- (4-cyano-2-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, ( ) -1- [2,2,2-trifluoro-1- (5-cyano-2-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (6-cyano-2-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2 , 2-trifluoro-1- (7-cyano-2-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-tri Fluoro-1- (8-cyano-2-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (1-nitro-2-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2 , 2-trifluoro-1- (3-nitro-2-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-tri Fluoro-1- (4-nitro-2-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (5-Nitro-2-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (6-nitro -2-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro-1- (7-nitro-2-naphthyl) ) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [2,2,2-trifluoro -1- (8-nitro-2-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxo-pyrazolidine and the like.

本発明の一般式(1)で表される光学活性5,5−ジメチル−3−オキソピペラゾリジン誘導体で、Rが置換基を有しても良いアリールエチレニル基であるものとしては、具体的には例えば、(S)−1−[1−(トリフルオロメチル)−3−フェニル−2−プロペン]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(2−メチルフェニル)−2−プロペン)]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(3−メチルフェニル)−2−プロペン)]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(4−メチルフェニル)−2−プロペン)]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(2−エチルフェニル)−2−プロペン)]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(3−エチルフェニル)−2−プロペン)]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(4−エチルフェニル)−2−プロペン)]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(2−n−プロピルフェニル)−2−プロペン)]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(3−n−プロピルフェニル)−2−プロペン)]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(4−n−プロピルフェニル)−2−プロペン)]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(2−iso−プロピルフェニル)−2−プロペン)]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(3−iso−プロピルフェニル)−2−プロペン)]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(4−iso−プロピルフェニル)−2−プロペン)]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(2−n−ブチルフェニル)−2−プロペン)]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(3−n−ブチルフェニル)−2−プロペン)]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(4−n−ブチルフェニル)−2−プロペン)]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(2−sec−ブチルフェニル)−2−プロペン)]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(3−sec−ブチルフェニル)−2−プロペン)]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(4−sec−ブチルフェニル)−2−プロペン)]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(2−tert−ブチルフェニル)−2−プロペン)]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(3−tert−ブチルフェニル)−2−プロペン)]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(4−tert−ブチルフェニル)−2−プロペン)]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(2−メトキシフェニル)−2−プロペン)]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(3−メトキシフェニル)−2−プロペン)]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(4−メトキシフェニル)−2−プロペン)]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(2−エトキシフェニル)−2−プロペン)]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(3−エトキシフェニル)−2−プロペン)]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(4−エトキシフェニル)−2−プロペン)]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(2−n−プロポキシフェニル)−2−プロペン)]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(3−n−プロポキシフェニル)−2−プロペン)]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(4−n−プロポキシフェニル)−2−プロペン)]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(2−iso−プロポキシフェニル)−2−プロペン)]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(3−iso−プロポキシフェニル)−2−プロペン)]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(4−iso−プロポキシフェニル)−2−プロペン)]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(2−n−ブトキシフェニル)−2−プロペン)]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(3−n−ブトキシフェニル)−2−プロペン)]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(4−n−ブトキシフェニル)−2−プロペン)]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(2−sec−ブトキシフェニル)−2−プロペン)]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(3−sec−ブトキシフェニル)−2−プロペン)]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(4−sec−ブトキシフェニル)−2−プロペン)]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(2−tert−ブトキシフェニル)−2−プロペン)]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(3−tert−ブトキシフェニル)−2−プロペン)]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(4−tert−ブトキシフェニル)−2−プロペン)]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(2−フルオロフェニル)−2−プロペン)]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(3−フルオロフェニル)−2−プロペン)]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(4−フルオロフェニル)−2−プロペン)]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(2−クロロフェニル)−2−プロペン)]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(3−クロロフェニル)−2−プロペン)]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(4−クロロフェニル)−2−プロペン)]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(2−ブロモフェニル)−2−プロペン)]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(3−ブロモフェニル)−2−プロペン)]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(4−ブロモフェニル)−2−プロペン)]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(2−シアノフェニル)−2−プロペン)]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(3−シアノフェニル)−2−プロペン)]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(4−シアノフェニル)−2−プロペン)]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(2−ニトロフェニル)−2−プロペン)]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(3−ニトロフェニル)−2−プロペン)]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(4−ニトロフェニル)−2−プロペン)]−5,5−ジメチル−3−オキソピラゾリジン等を挙げることができる。 In the optically active 5,5-dimethyl-3-oxopiperazolidine derivative represented by the general formula (1) of the present invention, R 3 is an arylethylenyl group which may have a substituent. Specifically, for example, (S) -1- [1- (trifluoromethyl) -3-phenyl-2-propene] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [ 1- (trifluoromethyl) -3- (2-methylphenyl) -2-propene)]-5,5-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (3-methylphenyl) -2-propene)]-5,5-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (4-methyl) Phenyl) -2-propene)]-5,5-dimethyl-3-oxopi Lazolidine, (S) -1- [1- (trifluoromethyl) -3- (2-ethylphenyl) -2-propene)]-5,5-dimethyl-3-oxopyrazolidine, (S) -1 -[1- (trifluoromethyl) -3- (3-ethylphenyl) -2-propene)]-5,5-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoro Methyl) -3- (4-ethylphenyl) -2-propene)]-5,5-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (2 -N-propylphenyl) -2-propene)]-5,5-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (3-n-propylphenyl) ) -2-propene)]-5,5-dimethyl-3-oxopyrazo Gin, (S) -1- [1- (trifluoromethyl) -3- (4-n-propylphenyl) -2-propene)]-5,5-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (2-iso-propylphenyl) -2-propene)]-5,5-dimethyl-3-oxopyrazolidine, (S) -1- [1 -(Trifluoromethyl) -3- (3-iso-propylphenyl) -2-propene)]-5,5-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl ) -3- (4-Iso-propylphenyl) -2-propene)]-5,5-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- ( 2-n-butylphenyl) -2-propene)]-5,5-di Tyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (3-n-butylphenyl) -2-propene)]-5,5-dimethyl-3-oxo Pyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (4-n-butylphenyl) -2-propene)]-5,5-dimethyl-3-oxopyrazolidine, ( S) -1- [1- (trifluoromethyl) -3- (2-sec-butylphenyl) -2-propene)]-5,5-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (3-sec-butylphenyl) -2-propene)]-5,5-dimethyl-3-oxopyrazolidine, (S) -1- [1- (tri Fluoromethyl) -3- (4-sec-butylphenyl) -2-propene) ] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (2-tert-butylphenyl) -2-propene)]-5,5 -Dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (3-tert-butylphenyl) -2-propene)]-5,5-dimethyl-3- Oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (4-tert-butylphenyl) -2-propene)]-5,5-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (2-methoxyphenyl) -2-propene)]-5,5-dimethyl-3-oxopyrazolidine, (S) -1- [ 1- (trifluoromethyl) -3- (3-methoxyphenyl -2-propene)]-5,5-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (4-methoxyphenyl) -2-propene)]- 5,5-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (2-ethoxyphenyl) -2-propene)]-5,5-dimethyl-3 -Oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (3-ethoxyphenyl) -2-propene)]-5,5-dimethyl-3-oxopyrazolidine, ( S) -1- [1- (trifluoromethyl) -3- (4-ethoxyphenyl) -2-propene)]-5,5-dimethyl-3-oxopyrazolidine, (S) -1- [1 -(Trifluoromethyl) -3- (2-n-propoxyphenyl) -2-propene)]-5,5-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (3-n-propoxyphenyl) -2-propene) ] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (4-n-propoxyphenyl) -2-propene)]-5,5 -Dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (2-iso-propoxyphenyl) -2-propene)]-5,5-dimethyl-3- Oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (3-iso-propoxyphenyl) -2-propene)]-5,5-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3 -(4-Iso-propoxyphenyl) -2-propene)]-5,5-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (2-n -Butoxyphenyl) -2-propene)]-5,5-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (3-n-butoxyphenyl)- 2-propene)]-5,5-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (4-n-butoxyphenyl) -2-propene)] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (2-sec-butoxyphenyl) -2-propene)]-5,5- Dimethyl-3-oxopyrazolidine, (S) -1- [1- ( (Rifluoromethyl) -3- (3-sec-butoxyphenyl) -2-propene)]-5,5-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl)- 3- (4-sec-butoxyphenyl) -2-propene)]-5,5-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (2- tert-butoxyphenyl) -2-propene)]-5,5-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (3-tert-butoxyphenyl) -2-propene)]-5,5-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (4-tert-butoxyphenyl) -2-propene) ] -5,5-dimethyl-3- Xopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (2-fluorophenyl) -2-propene)]-5,5-dimethyl-3-oxopyrazolidine, (S) -1 -[1- (trifluoromethyl) -3- (3-fluorophenyl) -2-propene)]-5,5-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoro Methyl) -3- (4-fluorophenyl) -2-propene)]-5,5-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (2 -Chlorophenyl) -2-propene)]-5,5-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (3-chlorophenyl) -2-propene) ] -5,5-dimethyl-3-oxopyrazo Lysine, (S) -1- [1- (trifluoromethyl) -3- (4-chlorophenyl) -2-propene)]-5,5-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (2-bromophenyl) -2-propene)]-5,5-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl ) -3- (3-Bromophenyl) -2-propene)]-5,5-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (4- Bromophenyl) -2-propene)]-5,5-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (2-cyanophenyl) -2-propene )]-5,5-dimethyl-3-oxopyrazolidine, (S)- -[1- (trifluoromethyl) -3- (3-cyanophenyl) -2-propene)]-5,5-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoro Methyl) -3- (4-cyanophenyl) -2-propene)]-5,5-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (2 -Nitrophenyl) -2-propene)]-5,5-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (3-nitrophenyl) -2- Propene)]-5,5-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (4-nitrophenyl) -2-propene)]-5,5 -Dimethyl-3-oxopyrazolidine etc. can be mentioned.

本発明の一般式(1)で表される光学活性5,5−ジメチル−3−オキソピペラゾリジン誘導体で、Rが置換基を有しても良いアリールアルキル基であるものとしては、具体的には例えば、(S)−1−[1−(トリフルオロメチル)−2−フェニルエチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−フェニルプロピル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−4−フェニルブチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−5−フェニルペンチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−6−フェニルヘキシル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−2−(2−メチルフェニル)エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−2−(3−メチルフェニル)エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−2−(4−メチルフェニル)エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(2−メチルフェニル)プロピル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(3−メチルフェニル)プロピル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(4−メチルフェニル)プロピル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−4−(2−メチルフェニル)ブチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−4−(3−メチルフェニル)ブチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−4−(4−メチルフェニル)ブチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−5−(2−メチルフェニル)ペンチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−5−(3−メチルフェニル)ペンチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−5−(4−メチルフェニル)ペンチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−2−(2−エチルフェニル)エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−2−(3−エチルフェニル)エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−2−(4−エチルフェニル)エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(2−エチルフェニル)プロピル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(3−エチルフェニル)プロピル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(4−エチルフェニル)プロピル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−4−(2−エチルフェニル)ブチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−4−(3−エチルフェニル)ブチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−4−(4−エチルフェニル)ブチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−5−(2−エチルフェニル)ペンチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−5−(3−エチルフェニル)ペンチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−5−(4−エチルフェニル)ペンチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−2−(2−メトキシフェニル)エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−2−(3−メトキシフェニル)エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−2−(4−メトキシフェニル)エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(2−メトキシフェニル)プロピル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(3−メトキシフェニル)プロピル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(4−メトキシフェニル)プロピル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−4−(2−メトキシフェニル)ブチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−4−(3−メトキシフェニル)ブチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−4−(4−メトキシフェニル)ブチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−5−(2−メトキシフェニル)ペンチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−5−(3−メトキシフェニル)ペンチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−5−(4−メトキシフェニル)ペンチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−2−(2−エトキシフェニル)エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−2−(3−エトキシフェニル)エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−2−(4−エトキシフェニル)エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(2−エトキシフェニル)プロピル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(3−エトキシフェニル)プロピル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(4−エトキシフェニル)プロピル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−4−(2−エトキシフェニル)ブチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−4−(3−エトキシフェニル)ブチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−4−(4−エトキシフェニル)ブチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−5−(2−エトキシフェニル)ペンチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−5−(3−エトキシフェニル)ペンチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−5−(4−エトキシフェニル)ペンチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−2−(2−フルオロフェニル)エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−2−(3−フルオロフェニル)エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−2−(4−フルオロフェニル)エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(2−フルオロフェニル)プロピル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(3−フルオロフェニル)プロピル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(4−フルオロフェニル)プロピル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−4−(2−フルオロフェニル)ブチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−4−(3−フルオロフェニル)ブチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−4−(4−フルオロフェニル)ブチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−5−(2−フルオロフェニル)ペンチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−5−(3−フルオロフェニル)ペンチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−5−(4−フルオロフェニル)ペンチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−2−(2−クロロフェニル)エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−2−(3−クロロフェニル)エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−2−(4−クロロフェニル)エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(2−クロロフェニル)プロピル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(3−クロロフェニル)プロピル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(4−クロロフェニル)プロピル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−4−(2−クロロフェニル)ブチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−4−(3−クロロフェニル)ブチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−4−(4−クロロフェニル)ブチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−5−(2−クロロフェニル)ペンチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−5−(3−クロロフェニル)ペンチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−5−(4−クロロフェニル)ペンチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−2−(2−ブロモフェニル)エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−2−(3−ブロモフェニル)エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−2−(4−ブロモフェニル)エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(2−ブロモフェニル)プロピル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(3−ブロモフェニル)プロピル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(4−ブロモフェニル)プロピル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1
−[1−(トリフルオロメチル)−4−(2−ブロモフェニル)ブチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−4−(3−ブロモフェニル)ブチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−4−(4−ブロモフェニル)ブチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−5−(2−ブロモフェニル)ペンチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−5−(3−ブロモフェニル)ペンチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−5−(4−ブロモフェニル)ペンチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−2−(2−シアノフェニル)エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−2−(3−シアノフェニル)エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−2−(4−シアノフェニル)エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(2−シアノフェニル)プロピル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(3−シアノフェニル)プロピル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(4−シアノフェニル)プロピル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−4−(2−シアノフェニル)ブチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−4−(3−シアノフェニル)ブチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−4−(4−シアノフェニル)ブチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−5−(2−シアノフェニル)ペンチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−5−(3−シアノフェニル)ペンチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−5−(4−シアノフェニル)ペンチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−2−(2−ニトロフェニル)エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−2−(3−ニトロフェニル)エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−2−(4−ニトロフェニル)エチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(2−ニトロフェニル)プロピル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(3−ニトロフェニル)プロピル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−3−(4−ニトロフェニル)プロピル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−4−(2−ニトロフェニル)ブチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−4−(3−ニトロフェニル)ブチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−4−(4−ニトロフェニル)ブチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−5−(2−ニトロフェニル)ブチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−5−(3−ニトロフェニル)ブチル]−5,5−ジメチル−3−オキソピラゾリジン、(S)−1−[1−(トリフルオロメチル)−5−(4−ニトロフェニル)ブチル]−5,5−ジメチル−3−オキソピラゾリジン等を挙げることができる。
The optically active 5,5-dimethyl-3-oxopiperazolidine derivative represented by the general formula (1) of the present invention, in which R 3 is an arylalkyl group which may have a substituent, Specifically, (S) -1- [1- (trifluoromethyl) -2-phenylethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [1- (tri Fluoromethyl) -3-phenylpropyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -4-phenylbutyl] -5,5-dimethyl- 3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -5-phenylpentyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [1- (Trifluoromethyl) -6-phenylhexyl]- 5,5-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -2- (2-methylphenyl) ethyl] -5,5-dimethyl-3-oxopyrazo Lysine, (S) -1- [1- (trifluoromethyl) -2- (3-methylphenyl) ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [1- (Trifluoromethyl) -2- (4-methylphenyl) ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (2- Methylphenyl) propyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (3-methylphenyl) propyl] -5,5-dimethyl -3-oxopyrazolidine, (S) -1- [1- ( (Rifluoromethyl) -3- (4-methylphenyl) propyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -4- (2-methyl) Phenyl) butyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -4- (3-methylphenyl) butyl] -5,5-dimethyl- 3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -4- (4-methylphenyl) butyl] -5,5-dimethyl-3-oxopyrazolidine, (S)- 1- [1- (trifluoromethyl) -5- (2-methylphenyl) pentyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl)- 5- (3-Methylphenyl) pentyl] -5 5-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -5- (4-methylphenyl) pentyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -2- (2-ethylphenyl) ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [1- (tri Fluoromethyl) -2- (3-ethylphenyl) ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -2- (4-ethylphenyl) ) Ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (2-ethylphenyl) propyl] -5,5-dimethyl-3 -Oxopyrazolidine, (S) -1- [1- (tri Fluoromethyl) -3- (3-ethylphenyl) propyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (4-ethylphenyl) ) Propyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -4- (2-ethylphenyl) butyl] -5,5-dimethyl-3 -Oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -4- (3-ethylphenyl) butyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1 -[1- (trifluoromethyl) -4- (4-ethylphenyl) butyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -5 -(2-Ethylphenyl) pentyl] -5,5 Dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -5- (3-ethylphenyl) pentyl] -5,5-dimethyl-3-oxopyrazolidine, (S ) -1- [1- (trifluoromethyl) -5- (4-ethylphenyl) pentyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) ) -2- (2-methoxyphenyl) ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -2- (3-methoxyphenyl) ethyl ] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -2- (4-methoxyphenyl) ethyl] -5,5-dimethyl-3-oxo Pyrazolidine, (S) -1- [1- ( (Rifluoromethyl) -3- (2-methoxyphenyl) propyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (3-methoxy Phenyl) propyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (4-methoxyphenyl) propyl] -5,5-dimethyl- 3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -4- (2-methoxyphenyl) butyl] -5,5-dimethyl-3-oxopyrazolidine, (S)- 1- [1- (trifluoromethyl) -4- (3-methoxyphenyl) butyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl)- 4- (4-Methoxyphenyl) bu Til] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -5- (2-methoxyphenyl) pentyl] -5,5-dimethyl-3- Oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -5- (3-methoxyphenyl) pentyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -5- (4-methoxyphenyl) pentyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -2- (2-Ethoxyphenyl) ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -2- (3-ethoxyphenyl) ethyl] -5, 5-dimethyl-3-oxopyrazolidine, S) -1- [1- (trifluoromethyl) -2- (4-ethoxyphenyl) ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoro Methyl) -3- (2-ethoxyphenyl) propyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (3-ethoxyphenyl) Propyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (4-ethoxyphenyl) propyl] -5,5-dimethyl-3- Oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -4- (2-ethoxyphenyl) butyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [1- (Trifluoromethyl) -4- (3 Ethoxyphenyl) butyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -4- (4-ethoxyphenyl) butyl] -5,5-dimethyl -3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -5- (2-ethoxyphenyl) pentyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -5- (3-ethoxyphenyl) pentyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -5- (4-Ethoxyphenyl) pentyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -2- (2-fluorophenyl) ethyl] -5,5-dimethyl-3- Oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -2- (3-fluorophenyl) ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -2- (4-fluorophenyl) ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (2-Fluorophenyl) propyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (3-fluorophenyl) propyl] -5, 5-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (4-fluorophenyl) propyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [1- (Trifluor Methyl) -4- (2-fluorophenyl) butyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -4- (3-fluorophenyl) Butyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -4- (4-fluorophenyl) butyl] -5,5-dimethyl-3- Oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -5- (2-fluorophenyl) pentyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -5- (3-fluorophenyl) pentyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -5- (4-Fluorophenyl) pentyl]- , 5-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -2- (2-chlorophenyl) ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -2- (3-chlorophenyl) ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoro Methyl) -2- (4-chlorophenyl) ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (2-chlorophenyl) propyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (3-chlorophenyl) propyl] -5,5-dimethyl-3-oxopyrazo Lysine, (S) -1- [1- (G (Rifluoromethyl) -3- (4-chlorophenyl) propyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -4- (2-chlorophenyl) Butyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -4- (3-chlorophenyl) butyl] -5,5-dimethyl-3-oxo Pyrazolidine, (S) -1- [1- (trifluoromethyl) -4- (4-chlorophenyl) butyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [1 -(Trifluoromethyl) -5- (2-chlorophenyl) pentyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -5- (3- Chlorophenyl) pentyl] -5 -Dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -5- (4-chlorophenyl) pentyl] -5,5-dimethyl-3-oxopyrazolidine, (S ) -1- [1- (trifluoromethyl) -2- (2-bromophenyl) ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) ) -2- (3-Bromophenyl) ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -2- (4-bromophenyl) ethyl ] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (2-bromophenyl) propyl] -5,5-dimethyl-3-oxo Pyrazolidine, (S) -1- [1- (tri (Luoromethyl) -3- (3-bromophenyl) propyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (4-bromophenyl) Propyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1
-[1- (trifluoromethyl) -4- (2-bromophenyl) butyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -4 -(3-Bromophenyl) butyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -4- (4-bromophenyl) butyl] -5 , 5-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -5- (2-bromophenyl) pentyl] -5,5-dimethyl-3-oxopyrazolidine (S) -1- [1- (trifluoromethyl) -5- (3-bromophenyl) pentyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [1- ( Trifluoromethyl) -5- (4-bromophenyl) pen L] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -2- (2-cyanophenyl) ethyl] -5,5-dimethyl-3- Oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -2- (3-cyanophenyl) ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -2- (4-cyanophenyl) ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (2-Cyanophenyl) propyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (3-cyanophenyl) propyl] -5, 5-dimethyl-3-oxopyrazolidine, (S) -1- 1- (trifluoromethyl) -3- (4-cyanophenyl) propyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -4- ( 2-cyanophenyl) butyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -4- (3-cyanophenyl) butyl] -5,5 -Dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -4- (4-cyanophenyl) butyl] -5,5-dimethyl-3-oxopyrazolidine, ( S) -1- [1- (trifluoromethyl) -5- (2-cyanophenyl) pentyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoro Methyl) -5- (3-cyanophenyl) pentyl ] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -5- (4-cyanophenyl) pentyl] -5,5-dimethyl-3-oxo Pyrazolidine, (S) -1- [1- (trifluoromethyl) -2- (2-nitrophenyl) ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [ 1- (trifluoromethyl) -2- (3-nitrophenyl) ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -2- ( 4-nitrophenyl) ethyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (2-nitrophenyl) propyl] -5,5 -Dimethyl-3-oxopyrazolidine, (S) -1- [1 (Trifluoromethyl) -3- (3-nitrophenyl) propyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -3- (4- Nitrophenyl) propyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -4- (2-nitrophenyl) butyl] -5,5-dimethyl -3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -4- (3-nitrophenyl) butyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -4- (4-nitrophenyl) butyl] -5,5-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -5- (2-Nitrophenyl) butyl]- , 5-dimethyl-3-oxopyrazolidine, (S) -1- [1- (trifluoromethyl) -5- (3-nitrophenyl) butyl] -5,5-dimethyl-3-oxopyrazolidine (S) -1- [1- (trifluoromethyl) -5- (4-nitrophenyl) butyl] -5,5-dimethyl-3-oxopyrazolidine and the like.

本発明の一般式(2)で表わされるN,N−ベタイン誘導体として、3−オキソピラゾリン骨格を有し、Rがメチル基、エチル基、炭素数3〜10の直鎖、分岐若しくは環式のアルキル基であるものとしては、具体的には例えば、1−(エチリデン)−3−オキソピラゾリジン N,N−ベタイン、1−(n−プロピリデン)−3−オキソピラゾリジン N,N−ベタイン、1−(n−ブチリデン)−3−オキソピラゾリジン N,N−ベタイン、1−(2−メチルプロピリデン)−3−オキソピラゾリジン N,N−ベタイン、1−(n−ペンチレリデン)−3−オキソピラゾリジン N,N−ベタイン、1−(2,2−ジメチルプロピリデン)−3−オキソピラゾリジン N,N−ベタイン、1−(n−ヘキシリデン)−3−オキソピラゾリジン N,N−ベタイン、1−(n−ヘプチリデン)−3−オキソピラゾリジン N,N−ベタイン、1−(シクロヘキシルメチリデン)−3−オキソピラゾリン N,N−ベタイン、1−(n−オクチリデン)−3−オキソピラゾリジン N,N−ベタイン、1−(n−ノナニリデン)−3−オキソピラゾリジン N,N−ベタイン、1−(n−デシリデン)−3−オキソピラゾリジン N,N−ベタイン、1−(n−ウンデシリデン)−3−オキソピラゾリジン N,N−ベタイン等を挙げることができる。 The N, N-betaine derivative represented by the general formula (2) of the present invention has a 3-oxopyrazoline skeleton, and R 3 is a methyl group, an ethyl group, a straight chain, branched or cyclic group having 3 to 10 carbon atoms. Specific examples of the alkyl group include 1- (ethylidene) -3-oxopyrazolidine N, N-betaine, 1- (n-propylidene) -3-oxopyrazolidine N, N- Betaine, 1- (n-butylidene) -3-oxopyrazolidine N, N-betaine, 1- (2-methylpropylidene) -3-oxopyrazolidine N, N-betaine, 1- (n-pentyllidene ) -3-Oxopyrazolidine N, N-betaine, 1- (2,2-dimethylpropylidene) -3-oxopyrazolidine N, N-betaine, 1- (n-hexylidene) -3-oxopyrazolid N, N-betaine, 1- (n-heptylidene) -3-oxopyrazolidine N, N-betaine, 1- (cyclohexylmethylidene) -3-oxopyrazoline N, N-betaine, 1- (n-octylidene ) -3-Oxopyrazolidine N, N-betaine, 1- (n-nonanilidene) -3-oxopyrazolidine N, N-betaine, 1- (n-decylidene) -3-oxopyrazolidine N, N-betaine, 1- (n-undecylidene) -3-oxopyrazolidine N, N-betaine and the like can be mentioned.

本発明の一般式(2)で表されるN,N−ベタイン誘導体として、3−オキソピラゾリン骨格を有し、Rが置換基を有しても良いフェニル基であるものとしては、具体的には例えば、1−ベンジリデン−3−オキソピラゾリジン N,N−ベタイン、1−(2−メチルフェニル)メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−(3−メチルフェニル)メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−(4−メチルフェニル)メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−(2−エチルフェニル)メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−(3−エチルフェニル)メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−(4−エチルフェニル)メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−(2−n−プロピルフェニル)メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−(3−n−プロピルフェニル)メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−(4−n−プロピルフェニル)メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−(2−iso−プロピルフェニル)メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−(3−iso−プロピルフェニル)メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−(4−iso−プロピルフェニル)メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−(2−n−ブチルフェニル)メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−(3−n−ブチルフェニル)メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−(4−n−ブチルフェニル)メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−(2−iso−ブチルフェニル)メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−(3−iso−ブチルフェニル)メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−(4−iso−ブチルフェニル)メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−(2−tert−ブチルフェニル)メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−(3−tert−ブチルフェニル)メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−(4−tert−ブチルフェニル)メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−(4−n−ペンチルフェニル)メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−(4−n−ヘキシルフェニル)メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−(4−n−ヘプチルフェニル)メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−(4−n−オクチルフェニル)メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−(4−n−ノニルフェニル)メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−(4−n−デシルフェニル)メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−(2−メトキシフェニル)メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−(3−メトキシフェニル)メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−(4−メトキシフェニル)メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−(2−エトキシフェニル)メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−(3−エトキシフェニル)メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−(4−エトキシフェニル)メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−(2−n−プロポキシフェニル)メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−(3−n−プロポキシフェニル)メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−(4−n−プロポキシフェニル)メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−(2−iso−プロポキシフェニル)メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−(3−iso−プロポキシフェニル)メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−(4−iso−プロポキシフェニル)メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−(2−n−ブトキシフェニル)メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−(3−n−ブトキシフェニル)メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−(4−n−ブトキシフェニル)メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−(2−iso−ブトキシフェニル)メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−(3−iso−ブトキシフェニル)メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−(4−iso−ブトキシフェニル)メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−(2−tert−ブトキシフェニル)メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−(3−tert−ブトキシフェニル)メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−(4−tert−ブトキシフェニル)メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−(4−n−ペントキシフェニル)メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−(4−n−ヘキシルオキシフェニル)メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−(4−n−ヘプチルオキシフェニル)メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−(4−n−オクチルオキシフェニル)メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−(4−n−ノニルオキシフェニル)メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−(4−n−デシルオキシフェニル)メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−(2−フルオロフェニル)メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−(3−フルオロフェニル)メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−(4−フルオロフェニル)メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−(2−クロロフェニル)メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−(3−クロロフェニル)メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−(4−クロロフェニル)メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−(2−ブロモフェニル)メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−(3−ブロモフェニル)メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−(4−ブロモフェニル)メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−(2−シアノフェニル)メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−(3−シアノフェニル)メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−(4−シアノフェニル)メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−(2−ニトロフェニル)メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−(3−ニトロフェニル)メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−(4−ニトロフェニル)メチリデン−3−オキソピラゾリジン N,N−ベタイン等を挙げることができる。 As the N, N-betaine derivative represented by the general formula (2) of the present invention, a compound having a 3-oxopyrazoline skeleton and R 3 may optionally have a substituent is specifically, For example, 1-benzylidene-3-oxopyrazolidine N, N-betaine, 1- (2-methylphenyl) methylidene-3-oxopyrazolidine N, N-betaine, 1- (3-methylphenyl) methylidene -3-oxopyrazolidine N, N-betaine, 1- (4-methylphenyl) methylidene-3-oxopyrazolidine N, N-betaine, 1- (2-ethylphenyl) methylidene-3-oxopyrazo Lysine N, N-betaine, 1- (3-ethylphenyl) methylidene-3-oxopyrazolidine N, N-betaine, 1- (4-ethylphenyl) methylidene-3-oxo Pyrazolidine N, N-betaine, 1- (2-n-propylphenyl) methylidene-3-oxopyrazolidine N, N-betaine, 1- (3-n-propylphenyl) methylidene-3-oxopyrazolidine N , N-betaine, 1- (4-n-propylphenyl) methylidene-3-oxopyrazolidine N, N-betaine, 1- (2-iso-propylphenyl) methylidene-3-oxopyrazolidine N, N -Betaine, 1- (3-iso-propylphenyl) methylidene-3-oxopyrazolidine N, N-betaine, 1- (4-iso-propylphenyl) methylidene-3-oxopyrazolidine N, N-betaine 1- (2-n-butylphenyl) methylidene-3-oxopyrazolidine N, N-betaine, 1- (3-n-butylphenyl) methyl Riden-3-oxopyrazolidine N, N-betaine, 1- (4-n-butylphenyl) methylidene-3-oxopyrazolidine N, N-betaine, 1- (2-iso-butylphenyl) methylidene- 3-oxopyrazolidine N, N-betaine, 1- (3-iso-butylphenyl) methylidene-3-oxopyrazolidine N, N-betaine, 1- (4-iso-butylphenyl) methylidene-3- Oxopyrazolidine N, N-betaine, 1- (2-tert-butylphenyl) methylidene-3-oxopyrazolidine N, N-betaine, 1- (3-tert-butylphenyl) methylidene-3-oxopyra Zolidine N, N-betaine, 1- (4-tert-butylphenyl) methylidene-3-oxopyrazolidine N, N-betaine, 1- (4 n-pentylphenyl) methylidene-3-oxopyrazolidine N, N-betaine, 1- (4-n-hexylphenyl) methylidene-3-oxopyrazolidine N, N-betaine, 1- (4-n- Heptylphenyl) methylidene-3-oxopyrazolidine N, N-betaine, 1- (4-n-octylphenyl) methylidene-3-oxopyrazolidine N, N-betaine, 1- (4-n-nonylphenyl) ) Methylidene-3-oxopyrazolidine N, N-betaine, 1- (4-n-decylphenyl) methylidene-3-oxopyrazolidine N, N-betaine, 1- (2-methoxyphenyl) methylidene-3 -Oxopyrazolidine N, N-betaine, 1- (3-methoxyphenyl) methylidene-3-oxopyrazolidine N, N-betaine, 1- (4- Methoxyphenyl) methylidene-3-oxopyrazolidine N, N-betaine, 1- (2-ethoxyphenyl) methylidene-3-oxopyrazolidine N, N-betaine, 1- (3-ethoxyphenyl) methylidene-3 -Oxopyrazolidine N, N-betaine, 1- (4-ethoxyphenyl) methylidene-3-oxopyrazolidine N, N-betaine, 1- (2-n-propoxyphenyl) methylidene-3-oxopyrazo Lysine N, N-betaine, 1- (3-n-propoxyphenyl) methylidene-3-oxopyrazolidine N, N-betaine, 1- (4-n-propoxyphenyl) methylidene-3-oxopyrazolidine N , N-betaine, 1- (2-iso-propoxyphenyl) methylidene-3-oxopyrazolidine N, N-betaine, 1 (3-iso-propoxyphenyl) methylidene-3-oxopyrazolidine N, N-betaine, 1- (4-iso-propoxyphenyl) methylidene-3-oxopyrazolidine N, N-betaine, 1- (2 -N-butoxyphenyl) methylidene-3-oxopyrazolidine N, N-betaine, 1- (3-n-butoxyphenyl) methylidene-3-oxopyrazolidine N, N-betaine, 1- (4-n -Butoxyphenyl) methylidene-3-oxopyrazolidine N, N-betaine, 1- (2-iso-butoxyphenyl) methylidene-3-oxopyrazolidine N, N-betaine, 1- (3-iso-butoxy Phenyl) methylidene-3-oxopyrazolidine N, N-betaine, 1- (4-iso-butoxyphenyl) methylidene-3-oxy Pyrazolidine N, N-betaine, 1- (2-tert-butoxyphenyl) methylidene-3-oxopyrazolidine N, N-betaine, 1- (3-tert-butoxyphenyl) methylidene-3-oxopyrazolidine N , N-betaine, 1- (4-tert-butoxyphenyl) methylidene-3-oxopyrazolidine N, N-betaine, 1- (4-n-pentoxyphenyl) methylidene-3-oxopyrazolidine N, N-betaine, 1- (4-n-hexyloxyphenyl) methylidene-3-oxopyrazolidine N, N-betaine, 1- (4-n-heptyloxyphenyl) methylidene-3-oxopyrazolidine N, N-betaine, 1- (4-n-octyloxyphenyl) methylidene-3-oxopyrazolidine N, N-betaine, 1- 4-n-nonyloxyphenyl) methylidene-3-oxopyrazolidine N, N-betaine, 1- (4-n-decyloxyphenyl) methylidene-3-oxopyrazolidine N, N-betaine, 1- ( 2-fluorophenyl) methylidene-3-oxopyrazolidine N, N-betaine, 1- (3-fluorophenyl) methylidene-3-oxopyrazolidine N, N-betaine, 1- (4-fluorophenyl) methylidene -3-oxopyrazolidine N, N-betaine, 1- (2-chlorophenyl) methylidene-3-oxopyrazolidine N, N-betaine, 1- (3-chlorophenyl) methylidene-3-oxopyrazolidine N , N-betaine, 1- (4-chlorophenyl) methylidene-3-oxopyrazolidine N, N-betaine, 1- (2-bromo Phenyl) methylidene-3-oxopyrazolidine N, N-betaine, 1- (3-bromophenyl) methylidene-3-oxopyrazolidine N, N-betaine, 1- (4-bromophenyl) methylidene-3- Oxopyrazolidine N, N-betaine, 1- (2-cyanophenyl) methylidene-3-oxopyrazolidine N, N-betaine, 1- (3-cyanophenyl) methylidene-3-oxopyrazolidine N, N-betaine, 1- (4-cyanophenyl) methylidene-3-oxopyrazolidine N, N-betaine, 1- (2-nitrophenyl) methylidene-3-oxopyrazolidine N, N-betaine, 1- (3-Nitrophenyl) methylidene-3-oxopyrazolidine N, N-betaine, 1- (4-nitrophenyl) methylidene-3-oxopyra Lysine N, N-betaine, and the like.

本発明の一般式(2)で表されるN,N−ベタイン誘導体として、3−オキソピラゾリン骨格を有し、Rが置換基を有しても良い1−ナフチル基であるものとしては、具体的には例えば、1−(1−ナフチルメチリデン)−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−メチルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(3−メチルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−メチルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(5−メチルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−メチルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(7−メチルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−メチルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−エチルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(3−エチルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−エチルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(5−エチルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−エチルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(7−エチルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−エチルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−n−プロピルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(3−n−プロピルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−n−プロピルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(5−n−プロピルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−n−プロピルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(7−n−プロピルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−n−プロピルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−iso−プロピルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(3−iso−プロピルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−iso−プロピルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(5−iso−プロピルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−iso−プロピルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(7−iso−プロピルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−iso−プロピルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−n−ブチルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(3−n−ブチルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−n−ブチルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(5−n−ブチルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−n−ブチルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(7−n−ブチルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−n−ブチルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−iso−ブチルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(3−iso−ブチルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−iso−ブチルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(5−iso−ブチルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−iso−ブチルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(7−iso−ブチルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−iso−ブチルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−tert−ブチルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(3−tert−ブチルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−tert−ブチルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(5−tert−ブチルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−tert−ブチルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(7−tert−ブチルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−tert−ブチルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−n−ペンチルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−n−ペンチルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−n−ペンチルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−n−ペンチルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−n−ヘキシルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−n−ヘキシルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−n−ヘキシルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−n−ヘキシルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−n−ヘプチルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−n−ヘプチルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−n−ヘプチルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−n−ヘプチルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−n−オクチルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−n−オクチルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−n−オクチルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−n−オクチルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−n−ノニルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−n−ノニルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−n−ノニルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−n−ノニルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−n−デシルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−n−デシルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−n−デシルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−n−デシルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−メトキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(3−メトキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−メトキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(5−メトキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−メトキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(7−メトキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−メトキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−エトキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(3−エトキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−エトキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(5−エトキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−エトキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(7−エトキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−エトキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−n−プロポキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(3−n−プロポキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−n−プロポキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(5−n−プロポキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−n−プロポキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(7−n−プロポキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−n−プロポキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−iso−プロポキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(3−iso−プロポキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−iso−プロポキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(5−iso−プロポキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−iso−プロポキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(7−iso−プロポキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−iso−プロポキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−n−ブトキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(3−n−ブトキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−n−ブトキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(5−n−ブトキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−n−ブトキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(7−n−ブトキシナフチル)]メチリデン−3−オキソピ
ラゾリジン N,N−ベタイン、1−[1−(8−n−ブトキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−iso−ブトキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(3−iso−ブトキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−iso−ブトキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(5−iso−ブトキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−iso−ブトキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(7−iso−ブトキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−iso−ブトキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−tert−ブトキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(3−tert−ブトキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−tert−ブトキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(5−tert−ブトキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−tert−ブトキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(7−tert−ブトキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−tert−ブトキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−n−ペントキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−n−ペントキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−n−ペントキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−n−ペントキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−n−ヘキシルオキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−n−ヘキシルオキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−n−ヘキシルオキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−n−ヘキシルオキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−n−ヘプチルオキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−n−ヘプチルオキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−n−ヘプチルオキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−n−ヘプチルオキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−n−オクチルオキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−n−オクチルオキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−n−オクチルオキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−n−オクチルオキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−n−ノニルオキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−n−ノニルオキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−n−ノニルオキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−n−ノニルオキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−n−デシルオキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−n−デシルオキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−n−デシルオキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−n−デシルオキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−フルオロナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(3−フルオロナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−フルオロナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(5−フルオロナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−フルオロナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(7−フルオロナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−フルオロナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−クロロナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(3−クロロナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−クロロナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(5−クロロナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−クロロナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(7−クロロナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−クロロナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−ブロモナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(3−ブロモナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−ブロモナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(5−ブロモナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−ブロモナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(7−ブロモナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−ブロモナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−シアノナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(3−シアノナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−シアノナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(5−シアノナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−シアノナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(7−シアノナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−シアノナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−ニトロナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(3−ニトロナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−ニトロナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(5−ニトロナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−ニトロナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(7−ニトロナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−ニトロナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン等を挙げることができる。
Examples of the N, N-betaine derivative represented by the general formula (2) of the present invention include a 3-oxopyrazoline skeleton, and R 3 is a 1-naphthyl group which may have a substituent. Specifically, for example, 1- (1-naphthylmethylidene) -3-oxopyrazolidine N, N-betaine, 1- [1- (2-methylnaphthyl)] methylidene-3-oxopyrazolidine N, N -Betaine, 1- [1- (3-methylnaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (4-methylnaphthyl)] methylidene-3-oxopyrazolidine N , N-betaine, 1- [1- (5-methylnaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (6-methylnaphthyl)] methylidene-3-oxopyrazolidine Lysine N, N- Betaine, 1- [1- (7-methylnaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (8-methylnaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (2-ethylnaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (3-ethylnaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (4-ethylnaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (5-ethylnaphthyl)] methylidene-3-oxopyrazine Zolidine N, N-betaine, 1- [1- (6-ethylnaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (7-ethylnaphthyl)] methylidene-3- Oxopyrazolidine N, N-betaine, 1- [1- (8-ethylnaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (2-n-propylnaphthyl)] Methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (3-n-propylnaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (4- n-propylnaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (5-n-propylnaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (6-n-propylnaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (7-n-propylnaphthyl)] methylidene-3-oxopyrazolidine N, -Betaine, 1- [1- (8-n-propylnaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (2-iso-propylnaphthyl)] methylidene-3-oxo Pyrazolidine N, N-betaine, 1- [1- (3-iso-propylnaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (4-iso-propylnaphthyl) ] Methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (5-iso-propylnaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (6 -Iso-propylnaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (7-iso-propylnaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (8-iso-propylnaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (2-n-butylnaphthyl)] methylidene- 3-oxopyrazolidine N, N-betaine, 1- [1- (3-n-butylnaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (4-n- Butylnaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (5-n-butylnaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [1 -(6-n-Butylnaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (7-n-butylnaphthyl)] methylidene-3-oxopyrazolidine N, N- Betaine, 1- [ -(8-n-Butylnaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (2-iso-butylnaphthyl)] methylidene-3-oxopyrazolidine N, N- Betaine, 1- [1- (3-iso-butylnaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (4-iso-butylnaphthyl)] methylidene-3-oxopyra Zolidine N, N-betaine, 1- [1- (5-iso-butylnaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (6-iso-butylnaphthyl)] Methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (7-iso-butylnaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (8 iso-butylnaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (2-tert-butylnaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (3-tert-butylnaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (4-tert-butylnaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (5-tert-butylnaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (6-tert-butylnaphthyl)] methylidene-3- Oxopyrazolidine N, N-betaine, 1- [1- (7-tert-butylnaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [ -(8-tert-butylnaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (2-n-pentylnaphthyl)] methylidene-3-oxopyrazolidine N, N- Betaine, 1- [1- (4-n-pentylnaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (6-n-pentylnaphthyl)] methylidene-3-oxopyra Zolidine N, N-betaine, 1- [1- (8-n-pentylnaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (2-n-hexylnaphthyl)] Methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (4-n-hexylnaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (6- n- Xylnaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (8-n-hexylnaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [1 -(2-n-heptylnaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (4-n-heptylnaphthyl)] methylidene-3-oxopyrazolidine N, N- Betaine, 1- [1- (6-n-heptylnaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (8-n-heptylnaphthyl)] methylidene-3-oxopyra Zolidine N, N-betaine, 1- [1- (2-n-octylnaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (4-n-octylnaphthyl) Methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (6-n-octylnaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (8- n-octylnaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (2-n-nonylnaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (4-n-nonylnaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (6-n-nonylnaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (8-n-nonylnaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (2-n-decylnaphthyl)] methylidene-3- Oxopyra Lysine N, N-betaine, 1- [1- (4-n-decylnaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (6-n-decylnaphthyl)] methylidene -3-Oxopyrazolidine N, N-betaine, 1- [1- (8-n-decylnaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (2-methoxy) Naphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (3-methoxynaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (4 -Methoxynaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (5-methoxynaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (6 Methoxynaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (7-methoxynaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- ( 8-methoxynaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (2-ethoxynaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [1 -(3-Ethoxynaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (4-ethoxynaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (5-Ethoxynaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (6-ethoxynaphthyl)] methylidene-3-oxopi Zolidine N, N-betaine, 1- [1- (7-ethoxynaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (8-ethoxynaphthyl)] methylidene-3-oxo Pyrazolidine N, N-betaine, 1- [1- (2-n-propoxynaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (3-n-propoxynaphthyl) ] Methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (4-n-propoxynaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (5 -N-propoxynaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (6-n-propoxynaphthyl)] methylidene-3-oxopyrazolidine N, N -Betaine, 1- [1- (7-n-propoxynaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (8-n-propoxynaphthyl)] methylidene-3-oxo Pyrazolidine N, N-betaine, 1- [1- (2-iso-propoxynaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (3-iso-propoxynaphthyl) ] Methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (4-iso-propoxynaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (5 -Iso-propoxynaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (6-iso-propoxynaphthyl)] methylidene-3-oxopi Zolidine N, N-betaine, 1- [1- (7-iso-propoxynaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (8-iso-propoxynaphthyl)] methylidene -3-oxopyrazolidine N, N-betaine, 1- [1- (2-n-butoxynaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (3-n -Butoxynaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (4-n-butoxynaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [ 1- (5-n-butoxynaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (6-n-butoxynaphthyl)] methylidene-3-oxopyrazoli N, N-betaine, 1- [1- (7-n-butoxynaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (8-n-butoxynaphthyl)] methylidene -3-oxopyrazolidine N, N-betaine, 1- [1- (2-iso-butoxynaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (3-iso -Butoxynaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (4-iso-butoxynaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [ 1- (5-iso-butoxynaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (6-iso-butoxynaphthyl)] methylidene-3-oxopyrazo Gin N, N-betaine, 1- [1- (7-iso-butoxynaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (8-iso-butoxynaphthyl)] methylidene -3-oxopyrazolidine N, N-betaine, 1- [1- (2-tert-butoxynaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (3-tert -Butoxynaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (4-tert-butoxynaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [ 1- (5-tert-Butoxynaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (6-tert-butoxynaphthyl)] methylide -3-oxopyrazolidine N, N-betaine, 1- [1- (7-tert-butoxynaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (8-tert -Butoxynaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (2-n-pentoxynaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (4-n-pentoxynaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (6-n-pentoxynaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (8-n-pentoxynaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (2-n-hexyloxynaphthyl)] Tylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (4-n-hexyloxynaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (6 -N-hexyloxynaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (8-n-hexyloxynaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine , 1- [1- (2-n-heptyloxynaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (4-n-heptyloxynaphthyl)] methylidene-3-oxo Pyrazolidine N, N-betaine, 1- [1- (6-n-heptyloxynaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (8-n-he Tyloxynaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (2-n-octyloxynaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (4-n-octyloxynaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (6-n-octyloxynaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (8-n-octyloxynaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (2-n-nonyloxynaphthyl)] Methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (4-n-nonyloxynaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1 [1- (6-n-nonyloxynaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (8-n-nonyloxynaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (2-n-decyloxynaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (4-n-decyloxynaphthyl)] Methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (6-n-decyloxynaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (8 -N-decyloxynaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (2-fluoronaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, -[1- (3-Fluoronaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (4-fluoronaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine 1- [1- (5-fluoronaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (6-fluoronaphthyl)] methylidene-3-oxopyrazolidine N, N -Betaine, 1- [1- (7-fluoronaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (8-fluoronaphthyl)] methylidene-3-oxopyrazolidine N , N-betaine, 1- [1- (2-chloronaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (3-chloronaphthyl)] methylidene-3 Oxopyrazolidine N, N-betaine, 1- [1- (4-chloronaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (5-chloronaphthyl)] methylidene- 3-oxopyrazolidine N, N-betaine, 1- [1- (6-chloronaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (7-chloronaphthyl)] Methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (8-chloronaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (2-bromonaphthyl) )] Methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (3-bromonaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (4- Bromo Naphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (5-bromonaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (6 -Bromonaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (7-bromonaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (8-bromonaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (2-cyanonaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [ 1- (3-cyanonaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (4-cyanonaphthyl)] methylidene-3-oxopyrazolidine N, N-beta 1- [1- (5-cyanonaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (6-cyanonaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (7-cyanonaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (8-cyanonaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (2-nitronaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (3-nitronaphthyl)] methylidene-3-oxopyrazine Zolidine N, N-betaine, 1- [1- (4-nitronaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (5-nitronaphthyl)] methylidene-3- Oki Pyrazolidine N, N-betaine, 1- [1- (6-nitronaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [1- (7-nitronaphthyl)] methylidene-3-oxo Examples include pyrazolidine N, N-betaine, 1- [1- (8-nitronaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine.

本発明の一般式(2)で表されるN,N−ベタイン誘導体として、3−オキソピラゾリン骨格を有し、Rが置換基を有しても良い2−ナフチル基であるものとしては、具体的には例えば、1−(2−ナフチルメチリデン)−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−メチルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(3−メチルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−メチルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(5−メチルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−メチルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(7−メチルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−メチルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−エチルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(3−エチルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−エチルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(5−エチルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−エチルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(7−エチルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−エチルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−n−プロピルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(3−n−プロピルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−n−プロピルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(5−n−プロピルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−n−プロピルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(7−n−プロピルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−n−プロピルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−iso−プロピルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(3−iso−プロピルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−iso−プロピルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(5−iso−プロピルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−iso−プロピルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(7−iso−プロピルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−iso−プロピルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−n−ブチルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(3−n−ブチルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−n−ブチルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(5−n−ブチルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−n−ブチルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(7−n−ブチルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−n−ブチルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−iso−ブチルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(3−iso−ブチルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−iso−ブチルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(5−iso−ブチルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−iso−ブチルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(7−iso−ブチルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−iso−ブチルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−tert−ブチルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(3−tert−ブチルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−tert−ブチルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(5−tert−ブチルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−tert−ブチルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(7−tert−ブチルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−tert−ブチルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−n−ペンチルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−n−ペンチルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−n−ペンチルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−n−ペンチルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−n−ヘキシルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−n−ヘキシルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−n−ヘキシルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−n−ヘキシルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−n−ヘプチルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−n−ヘプチルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−n−ヘプチルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−n−ヘプチルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−n−オクチルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−n−オクチルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−n−オクチルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−n−オクチルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−n−ノニルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−n−ノニルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−n−ノニルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−n−ノニルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−n−デシルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−n−デシルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−n−デシルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−n−デシルナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−メトキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(3−メトキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−メトキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(5−メトキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−メトキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(7−メトキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−メトキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−エトキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(3−エトキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−エトキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(5−エトキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−エトキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(7−エトキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−エトキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−n−プロポキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(3−n−プロポキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−n−プロポキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(5−n−プロポキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−n−プロポキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(7−n−プロポキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−n−プロポキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−iso−プロポキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(3−iso−プロポキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−iso−プロポキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(5−iso−プロポキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−iso−プロポキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(7−iso−プロポキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−iso−プロポキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−n−ブトキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(3−n−ブトキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−n−ブトキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(5−n−ブトキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−n−ブトキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(7−n−ブトキシナフチル)]メチリデン−3−オキソピ
ラゾリジン N,N−ベタイン、1−[2−(8−n−ブトキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−iso−ブトキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(3−iso−ブトキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−iso−ブトキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(5−iso−ブトキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−iso−ブトキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(7−iso−ブトキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−iso−ブトキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−tert−ブトキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(3−tert−ブトキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−tert−ブトキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(5−tert−ブトキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−tert−ブトキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(7−tert−ブトキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−tert−ブトキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−n−ペントキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−n−ペントキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−n−ペントキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−n−ペントキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−n−ヘキシルオキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−n−ヘキシルオキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−n−ヘキシルオキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−n−ヘキシルオキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−n−ヘプチルオキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−n−ヘプチルオキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−n−ヘプチルオキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−n−ヘプチルオキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−n−オクチルオキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−n−オクチルオキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−n−オクチルオキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−n−オクチルオキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−n−ノニルオキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−n−ノニルオキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−n−ノニルオキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−n−ノニルオキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−n−デシルオキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−n−デシルオキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−n−デシルオキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−n−デシルオキシナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−フルオロナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(3−フルオロナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−フルオロナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(5−フルオロナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−フルオロナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(7−フルオロナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−フルオロナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−クロロナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(3−クロロナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−クロロナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(5−クロロナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−クロロナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(7−クロロナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−クロロナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−ブロモナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(3−ブロモナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−ブロモナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(5−ブロモナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−ブロモナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(7−ブロモナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−ブロモナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−シアノナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(3−シアノナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−シアノナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(5−シアノナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−シアノナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(7−シアノナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−シアノナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−ニトロナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(3−ニトロナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−ニトロナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(5−ニトロナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−ニトロナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(7−ニトロナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−ニトロナフチル)]メチリデン−3−オキソピラゾリジン N,N−ベタイン等を挙げることができる。
As the N, N-betaine derivative represented by the general formula (2) of the present invention, the N, N-betaine derivative having a 3-oxopyrazoline skeleton, and R 3 may be optionally substituted is a 2-naphthyl group. Specifically, for example, 1- (2-naphthylmethylidene) -3-oxopyrazolidine N, N-betaine, 1- [2- (1-methylnaphthyl)] methylidene-3-oxopyrazolidine N, N -Betaine, 1- [2- (3-methylnaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (4-methylnaphthyl)] methylidene-3-oxopyrazolidine N , N-betaine, 1- [2- (5-methylnaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (6-methylnaphthyl)] methylidene-3-oxopyrazolidine Lysine N, N- Betaine, 1- [2- (7-methylnaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (8-methylnaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (1-ethylnaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (3-ethylnaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (4-ethylnaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (5-ethylnaphthyl)] methylidene-3-oxopyrazine Zolidine N, N-betaine, 1- [2- (6-ethylnaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (7-ethylnaphthyl)] methylidene-3- Oxopyrazolidine N, N-betaine, 1- [2- (8-ethylnaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (1-n-propylnaphthyl)] Methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (3-n-propylnaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (4- n-propylnaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (5-n-propylnaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (6-n-propylnaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (7-n-propylnaphthyl)] methylidene-3-oxopyrazolidine N, -Betaine, 1- [2- (8-n-propylnaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (1-iso-propylnaphthyl)] methylidene-3-oxo Pyrazolidine N, N-betaine, 1- [2- (3-iso-propylnaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (4-iso-propylnaphthyl) ] Methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (5-iso-propylnaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (6 -Iso-propylnaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (7-iso-propylnaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (8-iso-propylnaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (1-n-butylnaphthyl)] methylidene- 3-oxopyrazolidine N, N-betaine, 1- [2- (3-n-butylnaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (4-n- Butylnaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (5-n-butylnaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [2 -(6-n-Butylnaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (7-n-butylnaphthyl)] methylidene-3-oxopyrazolidine N, N- Betaine, 1- [ -(8-n-Butylnaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (1-iso-butylnaphthyl)] methylidene-3-oxopyrazolidine N, N- Betaine, 1- [2- (3-iso-butylnaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (4-iso-butylnaphthyl)] methylidene-3-oxopyra Zolidine N, N-betaine, 1- [2- (5-iso-butylnaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (6-iso-butylnaphthyl)] Methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (7-iso-butylnaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (8 iso-butylnaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (1-tert-butylnaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (3-tert-Butylnaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (4-tert-butylnaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (5-tert-butylnaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (6-tert-butylnaphthyl)] methylidene-3- Oxopyrazolidine N, N-betaine, 1- [2- (7-tert-butylnaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [ -(8-tert-Butylnaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (1-n-pentylnaphthyl)] methylidene-3-oxopyrazolidine N, N- Betaine, 1- [2- (4-n-pentylnaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (6-n-pentylnaphthyl)] methylidene-3-oxopyra Zolidine N, N-betaine, 1- [2- (8-n-pentylnaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (1-n-hexylnaphthyl)] Methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (4-n-hexylnaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (6- n- Xylnaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (8-n-hexylnaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [2 -(1-n-heptylnaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (4-n-heptylnaphthyl)] methylidene-3-oxopyrazolidine N, N- Betaine, 1- [2- (6-n-heptylnaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (8-n-heptylnaphthyl)] methylidene-3-oxopyra Zolidine N, N-betaine, 1- [2- (1-n-octylnaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (4-n-octylnaphthyl) Methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (6-n-octylnaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (8- n-octylnaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (1-n-nonylnaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (4-n-nonylnaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (6-n-nonylnaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (8-n-nonylnaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (1-n-decylnaphthyl)] methylidene-3- Oxopyra Lysine N, N-betaine, 1- [2- (4-n-decylnaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (6-n-decylnaphthyl)] methylidene -3-oxopyrazolidine N, N-betaine, 1- [2- (8-n-decylnaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (1-methoxy) Naphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (3-methoxynaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (4 -Methoxynaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (5-methoxynaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (6 Methoxynaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (7-methoxynaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- ( 8-methoxynaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (1-ethoxynaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [2 -(3-Ethoxynaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (4-ethoxynaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (5-Ethoxynaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (6-ethoxynaphthyl)] methylidene-3-oxopi Zolidine N, N-betaine, 1- [2- (7-ethoxynaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (8-ethoxynaphthyl)] methylidene-3-oxo Pyrazolidine N, N-betaine, 1- [2- (1-n-propoxynaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (3-n-propoxynaphthyl) ] Methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (4-n-propoxynaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (5 -N-propoxynaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (6-n-propoxynaphthyl)] methylidene-3-oxopyrazolidine N, N -Betaine, 1- [2- (7-n-propoxynaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (8-n-propoxynaphthyl)] methylidene-3-oxo Pyrazolidine N, N-betaine, 1- [2- (1-iso-propoxynaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (3-iso-propoxynaphthyl) ] Methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (4-iso-propoxynaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (5 -Iso-propoxynaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (6-iso-propoxynaphthyl)] methylidene-3-oxopi Zolidine N, N-betaine, 1- [2- (7-iso-propoxynaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (8-iso-propoxynaphthyl)] methylidene -3-oxopyrazolidine N, N-betaine, 1- [2- (1-n-butoxynaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (3-n -Butoxynaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (4-n-butoxynaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [ 2- (5-n-Butoxynaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (6-n-butoxynaphthyl)] methylidene-3-oxopyrazoli N, N-betaine, 1- [2- (7-n-butoxynaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (8-n-butoxynaphthyl)] methylidene -3-oxopyrazolidine N, N-betaine, 1- [2- (1-iso-butoxynaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (3-iso -Butoxynaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (4-iso-butoxynaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [ 2- (5-iso-butoxynaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (6-iso-butoxynaphthyl)] methylidene-3-oxopyrazo Gin N, N-betaine, 1- [2- (7-iso-butoxynaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (8-iso-butoxynaphthyl)] methylidene -3-oxopyrazolidine N, N-betaine, 1- [2- (1-tert-butoxynaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (3-tert -Butoxynaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (4-tert-butoxynaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [ 2- (5-tert-Butoxynaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (6-tert-butoxynaphthyl)] methylide -3-oxopyrazolidine N, N-betaine, 1- [2- (7-tert-butoxynaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (8-tert -Butoxynaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (1-n-pentoxynaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (4-n-pentoxynaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (6-n-pentoxynaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (8-n-pentoxynaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (1-n-hexyloxynaphthyl)] Tylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (4-n-hexyloxynaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (6 -N-hexyloxynaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (8-n-hexyloxynaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine , 1- [2- (1-n-heptyloxynaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (4-n-heptyloxynaphthyl)] methylidene-3-oxo Pyrazolidine N, N-betaine, 1- [2- (6-n-heptyloxynaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (8-n-he Tiloxynaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (1-n-octyloxynaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (4-n-octyloxynaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (6-n-octyloxynaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (8-n-octyloxynaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (1-n-nonyloxynaphthyl)] Methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (4-n-nonyloxynaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1 [2- (6-n-nonyloxynaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (8-n-nonyloxynaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (1-n-decyloxynaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (4-n-decyloxynaphthyl)] Methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (6-n-decyloxynaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (8 -N-decyloxynaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (1-fluoronaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, -[2- (3-Fluoronaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (4-fluoronaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine 1- [2- (5-fluoronaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (6-fluoronaphthyl)] methylidene-3-oxopyrazolidine N, N -Betaine, 1- [2- (7-fluoronaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (8-fluoronaphthyl)] methylidene-3-oxopyrazolidine N , N-betaine, 1- [2- (1-chloronaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (3-chloronaphthyl)] methylidene-3 Oxopyrazolidine N, N-betaine, 1- [2- (4-chloronaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (5-chloronaphthyl)] methylidene- 3-oxopyrazolidine N, N-betaine, 1- [2- (6-chloronaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (7-chloronaphthyl)] Methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (8-chloronaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (1-bromonaphthyl) )] Methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (3-bromonaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (4- Bromo Naphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (5-bromonaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (6 -Bromonaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (7-bromonaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (8-bromonaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (1-cyanonaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [ 2- (3-cyanonaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (4-cyanonaphthyl)] methylidene-3-oxopyrazolidine N, N-beta 1- [2- (5-cyanonaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (6-cyanonaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (7-cyanonaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (8-cyanonaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (1-nitronaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (3-nitronaphthyl)] methylidene-3-oxopyrazine Zolidine N, N-betaine, 1- [2- (4-nitronaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (5-nitronaphthyl)] methylidene-3- Oki Pyrazolidine N, N-betaine, 1- [2- (6-nitronaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, 1- [2- (7-nitronaphthyl)] methylidene-3-oxo Examples include pyrazolidine N, N-betaine, 1- [2- (8-nitronaphthyl)] methylidene-3-oxopyrazolidine N, N-betaine, and the like.

本発明の一般式(2)で表されるN,N−ベタイン誘導体として、3−オキソピラゾリン骨格を有し、Rが置換基を有しても良いアリールエチレニル基であるものとしては、具体的には例えば、1−(3−フェニルプロピリデン−2−エン)−3−オキソピラゾリジン N,N−ベタイン、1−[3−(2−メチルフェニル)プロピリデン−2−エン]−3−オキソピラゾリジン N,N−ベタイン、1−[3−(3−メチルフェニル)プロピリデン−2−エン]−3−オキソピラゾリジン N,N−ベタイン、1−[3−(4−メチルフェニル)プロピリデン−2−エン]−3−オキソピラゾリジン N,N−ベタイン、1−[3−(2−エチルフェニル)プロピリデン−2−エン]−3−オキソピラゾリジン N,N−ベタイン、1−[3−(3−エチルフェニル)プロピリデン−2−エン]−3−オキソピラゾリジン N,N−ベタイン、1−[3−(4−エチルフェニル)プロピリデン−2−エン]−3−オキソピラゾリジン N,N−ベタイン、1−[3−(2−n−プロピルフェニル)プロピリデン−2−エン]−3−オキソピラゾリジン N,N−ベタイン、1−[3−(3−n−プロピルフェニル)プロピリデン−2−エン]−3−オキソピラゾリジン N,N−ベタイン、1−[3−(4−n−プロピルフェニル)プロピリデン−2−エン]−3−オキソピラゾリジン N,N−ベタイン、1−[3−(2−iso−プロピルフェニル)プロピリデン−2−エン]−3−オキソピラゾリジン N,N−ベタイン、1−[3−(3−iso−プロピルフェニル)プロピリデン−2−エン]−3−オキソピラゾリジン N,N−ベタイン、1−[3−(4−iso−プロピルフェニル)プロピリデン−2−エン]−3−オキソピラゾリジン N,N−ベタイン、1−[3−(2−n−ブチルフェニル)プロピリデン−2−エン]−3−オキソピラゾリジン N,N−ベタイン、1−[3−(3−n−ブチルフェニル)プロピリデン−2−エン]−3−オキソピラゾリジン N,N−ベタイン、1−[3−(4−n−ブチルフェニル)プロピリデン−2−エン]−3−オキソピラゾリジン N,N−ベタイン、1−[3−(2−sec−ブチルフェニル)プロピリデン−2−エン]−3−オキソピラゾリジン N,N−ベタイン、1−[3−(3−sec−ブチルフェニル)プロピリデン−2−エン]−3−オキソピラゾリジン N,N−ベタイン、1−[3−(4−sec−ブチルフェニル)プロピリデン−2−エン]−3−オキソピラゾリジン N,N−ベタイン、1−[3−(2−tert−ブチルフェニル)プロピリデン−2−エン]−3−オキソピラゾリジン N,N−ベタイン、1−[3−(3−tert−ブチルフェニル)プロピリデン−2−エン]−3−オキソピラゾリジン N,N−ベタイン、1−[3−(4−tert−ブチルフェニル)プロピリデン−2−エン]−3−オキソピラゾリジン N,N−ベタイン、1−[3−(2−メトキシフェニル)プロピリデン−2−エン]−3−オキソピラゾリジン N,N−ベタイン、1−[3−(3−メトキシフェニル)プロピリデン−2−エン]−3−オキソピラゾリジン N,N−ベタイン、1−[3−(4−メトキシフェニル)プロピリデン−2−エン]−3−オキソピラゾリジン N,N−ベタイン、1−[3−(2−エトキシフェニル)プロピリデン−2−エン]−3−オキソピラゾリジン N,N−ベタイン、1−[3−(3−エトキシフェニル)プロピリデン−2−エン]−3−オキソピラゾリジン N,N−ベタイン、1−[3−(4−エトキシフェニル)プロピリデン−2−エン]−3−オキソピラゾリジン N,N−ベタイン、1−[3−(2−n−プロポキシフェニル)プロピリデン−2−エン]−3−オキソピラゾリジン N,N−ベタイン、1−[3−(3−n−プロポキシフェニル)プロピリデン−2−エン]−3−オキソピラゾリジン N,N−ベタイン、1−[3−(4−n−プロポキシフェニル)プロピリデン−2−エン]−3−オキソピラゾリジン N,N−ベタイン、1−[3−(2−iso−プロポキシフェニル)プロピリデン−2−エン]−3−オキソピラゾリジン N,N−ベタイン、1−[3−(3−iso−プロポキシフェニル)プロピリデン−2−エン]−3−オキソピラゾリジン N,N−ベタイン、1−[3−(4−iso−プロポキシフェニル)プロピリデン−2−エン]−3−オキソピラゾリジン N,N−ベタイン、1−[3−(2−n−ブトキシフェニル)プロピリデン−2−エン]−3−オキソピラゾリジン N,N−ベタイン、1−[3−(3−n−ブトキシフェニル)プロピリデン−2−エン]−3−オキソピラゾリジン N,N−ベタイン、1−[3−(4−n−ブトキシフェニル)プロピリデン−2−エン]−3−オキソピラゾリジン N,N−ベタイン、1−[3−(2−sec−ブトキシフェニル)プロピリデン−2−エン]−3−オキソピラゾリジン N,N−ベタイン、1−[3−(3−sec−ブトキシフェニル)プロピリデン−2−エン]−3−オキソピラゾリジン N,N−ベタイン、1−[3−(4−sec−ブトキシフェニル)プロピリデン−2−エン]−3−オキソピラゾリジン N,N−ベタイン、1−[3−(2−tert−ブトキシフェニル)プロピリデン−2−エン]−3−オキソピラゾリジン N,N−ベタイン、1−[3−(3−tert−ブトキシフェニル)プロピリデン−2−エン]−3−オキソピラゾリジン N,N−ベタイン、1−[3−(4−tert−ブトキシフェニル)プロピリデン−2−エン]−3−オキソピラゾリジン N,N−ベタイン、1−[3−(2−フルオロフェニル)プロピリデン−2−エン]−3−オキソピラゾリジン N,N−ベタイン、1−[3−(3−フルオロフェニル)プロピリデン−2−エン]−3−オキソピラゾリジン N,N−ベタイン、1−[3−(4−フルオロフェニル)プロピリデン−2−エン]−3−オキソピラゾリジン N,N−ベタイン、1−[3−(2−クロロフェニル)プロピリデン−2−エン]−3−オキソピラゾリジン N,N−ベタイン、1−[3−(3−クロロフェニル)プロピリデン−2−エン]−3−オキソピラゾリジン N,N−ベタイン、1−[3−(4−クロロフェニル)プロピリデン−2−エン]−3−オキソピラゾリジン N,N−ベタイン、1−[3−(2−ブロモフェニル)プロピリデン−2−エン]−3−オキソピラゾリジン N,N−ベタイン、1−[3−(3−ブロモフェニル)プロピリデン−2−エン]−3−オキソピラゾリジン N,N−ベタイン、1−[3−(4−ブロモフェニル)プロピリデン−2−エン]−3−オキソピラゾリジン N,N−ベタイン、1−[3−(2−シアノフェニル)プロピリデン−2−エン]−3−オキソピラゾリジン N,N−ベタイン、1−[3−(3−シアノフェニル)プロピリデン−2−エン]−3−オキソピラゾリジン N,N−ベタイン、1−[3−(4−シアノフェニル)プロピリデン−2−エン]−3−オキソピラゾリジン N,N−ベタイン、1−[3−(2−ニトロフェニル)プロピリデン−2−エン]−3−オキソピラゾリジン N,N−ベタイン、1−[3−(3−ニトロフェニル)プロピリデン−2−エン]−3−オキソピラゾリジン N,N−ベタイン、1−[3−(4−ニトロフェニル)プロピリデン−2−エン]−3−オキソピラゾリジン N,N−ベタイン等を挙げることができる。 The N, N-betaine derivative represented by the general formula (2) of the present invention has a 3-oxopyrazoline skeleton, and R 3 is an arylethylenyl group which may have a substituent. Specifically, for example, 1- (3-phenylpropylidene-2-ene) -3-oxopyrazolidine N, N-betaine, 1- [3- (2-methylphenyl) propylidene-2-ene] -3- Oxopyrazolidine N, N-betaine, 1- [3- (3-methylphenyl) propylidene-2-ene] -3-oxopyrazolidine N, N-betaine, 1- [3- (4-methylphenyl) ) Propylidene-2-ene] -3-oxopyrazolidine N, N-betaine, 1- [3- (2-ethylphenyl) propylidene-2-ene] -3-oxopyrazolidine N, N-betaine, 1- [3- 3-ethylphenyl) propylidene-2-ene] -3-oxopyrazolidine N, N-betaine, 1- [3- (4-ethylphenyl) propylidene-2-ene] -3-oxopyrazolidine N, N-betaine, 1- [3- (2-n-propylphenyl) propylidene-2-ene] -3-oxopyrazolidine N, N-betaine, 1- [3- (3-n-propylphenyl) propylidene 2-ene] -3-oxopyrazolidine N, N-betaine, 1- [3- (4-n-propylphenyl) propylidene-2-ene] -3-oxopyrazolidine N, N-betaine, 1- [3- (2-Iso-propylphenyl) propylidene-2-ene] -3-oxopyrazolidine N, N-betaine, 1- [3- (3-iso-propylphenyl) propylidene- -Ene] -3-oxopyrazolidine N, N-betaine, 1- [3- (4-iso-propylphenyl) propylidene-2-ene] -3-oxopyrazolidine N, N-betaine, 1- [3- (2-n-butylphenyl) propylidene-2-ene] -3-oxopyrazolidine N, N-betaine, 1- [3- (3-n-butylphenyl) propylidene-2-ene]- 3-oxopyrazolidine N, N-betaine, 1- [3- (4-n-butylphenyl) propylidene-2-ene] -3-oxopyrazolidine N, N-betaine, 1- [3- ( 2-sec-butylphenyl) propylidene-2-ene] -3-oxopyrazolidine N, N-betaine, 1- [3- (3-sec-butylphenyl) propylidene-2-ene] -3-oxopyra Zolidine N N-betaine, 1- [3- (4-sec-butylphenyl) propylidene-2-ene] -3-oxopyrazolidine N, N-betaine, 1- [3- (2-tert-butylphenyl) propylidene 2-ene] -3-oxopyrazolidine N, N-betaine, 1- [3- (3-tert-butylphenyl) propylidene-2-ene] -3-oxopyrazolidine N, N-betaine, 1- [3- (4-tert-butylphenyl) propylidene-2-ene] -3-oxopyrazolidine N, N-betaine, 1- [3- (2-methoxyphenyl) propylidene-2-ene]- 3-oxopyrazolidine N, N-betaine, 1- [3- (3-methoxyphenyl) propylidene-2-ene] -3-oxopyrazolidine N, N-betaine, 1- [3- (4- Me Toxiphenyl) propylidene-2-ene] -3-oxopyrazolidine N, N-betaine, 1- [3- (2-ethoxyphenyl) propylidene-2-ene] -3-oxopyrazolidine N, N- Betaine, 1- [3- (3-ethoxyphenyl) propylidene-2-ene] -3-oxopyrazolidine N, N-betaine, 1- [3- (4-ethoxyphenyl) propylidene-2-ene]- 3-oxopyrazolidine N, N-betaine, 1- [3- (2-n-propoxyphenyl) propylidene-2-ene] -3-oxopyrazolidine N, N-betaine, 1- [3- ( 3-n-propoxyphenyl) propylidene-2-ene] -3-oxopyrazolidine N, N-betaine, 1- [3- (4-n-propoxyphenyl) propylidin-2-ene] -3 Oxopyrazolidine N, N-betaine, 1- [3- (2-iso-propoxyphenyl) propylidin-2-ene] -3-oxopyrazolidine N, N-betaine, 1- [3- (3- iso-propoxyphenyl) propylidene-2-ene] -3-oxopyrazolidine N, N-betaine, 1- [3- (4-iso-propoxyphenyl) propylidene-2-ene] -3-oxopyrazolidine N, N-betaine, 1- [3- (2-n-butoxyphenyl) propylidene-2-ene] -3-oxopyrazolidine N, N-betaine, 1- [3- (3-n-butoxyphenyl) ) Propylidene-2-ene] -3-oxopyrazolidine N, N-betaine, 1- [3- (4-n-butoxyphenyl) propylidene-2-ene] -3-oxopyrazolidine , N-betaine, 1- [3- (2-sec-butoxyphenyl) propylidene-2-ene] -3-oxopyrazolidine N, N-betaine, 1- [3- (3-sec-butoxyphenyl) Propylidene-2-ene] -3-oxopyrazolidine N, N-betaine, 1- [3- (4-sec-butoxyphenyl) propylidene-2-ene] -3-oxopyrazolidine N, N-betaine 1- [3- (2-tert-butoxyphenyl) propylidene-2-ene] -3-oxopyrazolidine N, N-betaine, 1- [3- (3-tert-butoxyphenyl) propylidene-2- Ene] -3-oxopyrazolidine N, N-betaine, 1- [3- (4-tert-butoxyphenyl) propylidene-2-ene] -3-oxopyrazolidine N, N- Thane, 1- [3- (2-fluorophenyl) propylidene-2-ene] -3-oxopyrazolidine N, N-betaine, 1- [3- (3-fluorophenyl) propylidene-2-ene]- 3-oxopyrazolidine N, N-betaine, 1- [3- (4-fluorophenyl) propylidene-2-ene] -3-oxopyrazolidine N, N-betaine, 1- [3- (2- Chlorophenyl) propylidene-2-ene] -3-oxopyrazolidine N, N-betaine, 1- [3- (3-chlorophenyl) propylidene-2-ene] -3-oxopyrazolidine N, N-betaine, 1- [3- (4-Chlorophenyl) propylidene-2-ene] -3-oxopyrazolidine N, N-betaine, 1- [3- (2-bromophenyl) propylidene-2-ene] -3 -Oxopyrazolidine N, N-betaine, 1- [3- (3-bromophenyl) propylidene-2-ene] -3-oxopyrazolidine N, N-betaine, 1- [3- (4-bromo Phenyl) propylidene-2-ene] -3-oxopyrazolidine N, N-betaine, 1- [3- (2-cyanophenyl) propylidene-2-ene] -3-oxopyrazolidine N, N-betaine 1- [3- (3-cyanophenyl) propylidene-2-ene] -3-oxopyrazolidine N, N-betaine, 1- [3- (4-cyanophenyl) propylidin-2-ene] -3 -Oxopyrazolidine N, N-betaine, 1- [3- (2-nitrophenyl) propylidene-2-ene] -3-oxopyrazolidine N, N-betaine, 1- [3- (3-nitro Phenyl) pro Pyridene-2-ene] -3-oxopyrazolidine N, N-betaine, 1- [3- (4-nitrophenyl) propylidene-2-ene] -3-oxopyrazolidine N, N-betaine and the like. Can be mentioned.

本発明の一般式(2)で表されるN,N−ベタイン誘導体として、3−オキソピラゾリン骨格を有し、Rが置換基を有しても良いアリールアルキル基であるものとしては、具体的には例えば、1−(2−フェニルエチリデン)−3−オキソピラゾリジン N,N−ベタイン、1−(3−フェニルプロピリデン)−3−オキソピラゾリジン N,N−ベタイン、1−(4−フェニルブチリデン)−3−オキソピラゾリジン N,N−ベタイン、1−(5−フェニルペンチリデン)−3−オキソピラゾリジン N,N−ベタイン、1−(6−フェニルヘキシリデン)−3−オキソピラゾリジン N,N−ベタイン、1−[2−(2−メチルフェニル)エチリデン]−3−オキソピラゾリジン N,N−ベタイン、1−[2−(3−メチルフェニル)エチリデン]−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−メチルフェニル)エチリデン]−3−オキソピラゾリジン N,N−ベタイン、1−[3−(2−メチルフェニル)プロピリデン]−3−オキソピラゾリジン N,N−ベタイン、1−[3−(3−メチルフェニル)プロピリデン]−3−オキソピラゾリジン N,N−ベタイン、1−[3−(4−メチルフェニル)プロピリデン]−3−オキソピラゾリジン N,N−ベタイン、1−[4−(2−メチルフェニル)ブチリデン]−3−オキソピラゾリジン N,N−ベタイン、1−[4−(3−メチルフェニル)ブチリデン]−3−オキソピラゾリジン N,N−ベタイン、1−[4−(4−メチルフェニル)ブチリデン]−3−オキソピラゾリジン N,N−ベタイン、1−[5−(2−メチルフェニル)ペンチリデン]−3−オキソピラゾリジン N,N−ベタイン、1−[5−(3−メチルフェニル)ペンチリデン]−3−オキソピラゾリジン N,N−ベタイン、1−[5−(4−メチルフェニル)ペンチリデン]−3−オキソピラゾリジン N,N−ベタイン、1−[2−(2−エチルフェニル)エチリデン]−3−オキソピラゾリジン N,N−ベタイン、1−[2−(3−エチルフェニル)エチリデン]−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−エチルフェニル)エチリデン]−3−オキソピラゾリジン N,N−ベタイン、1−[3−(2−エチルフェニル)プロピリデン]−3−オキソピラゾリジン N,N−ベタイン、1−[3−(3−エチルフェニル)プロピリデン]−3−オキソピラゾリジン N,N−ベタイン、1−[3−(4−エチルフェニル)プロピリデン]−3−オキソピラゾリジン N,N−ベタイン、1−[4−(2−エチルフェニル)ブチリデン]−3−オキソピラゾリジン N,N−ベタイン、1−[4−(3−エチルフェニル)ブチリデン]−3−オキソピラゾリジン N,N−ベタイン、1−[4−(4−エチルフェニル)ブチリデン]−3−オキソピラゾリジン N,N−ベタイン、1−[5−(2−エチルフェニル)ペンチリデン]−3−オキソピラゾリジン N,N−ベタイン、1−[5−(3−エチルフェニル)ペンチリデン]−3−オキソピラゾリジン N,N−ベタイン、1−[5−(4−エチルフェニル)ペンチリデン]−3−オキソピラゾリジン N,N−ベタイン、1−[2−(2−メトキシフェニル)エチリデン]−3−オキソピラゾリジン N,N−ベタイン、1−[2−(3−メトキシフェニル)エチリデン]−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−メトキシフェニル)エチリデン]−3−オキソピラゾリジン N,N−ベタイン、1−[3−(2−メトキシフェニル)プロピリデン]−3−オキソピラゾリジン N,N−ベタイン、1−[3−(3−メトキシフェニル)プロピリデン]−3−オキソピラゾリジン N,N−ベタイン、1−[3−(4−メトキシフェニル)プロピリデン]−3−オキソピラゾリジン N,N−ベタイン、1−[4−(2−メトキシフェニル)ブチリデン]−3−オキソピラゾリジン N,N−ベタイン、1−[4−(3−メトキシフェニル)ブチリデン]−3−オキソピラゾリジン N,N−ベタイン、1−[4−(4−メトキシフェニル)ブチリデン]−3−オキソピラゾリジン N,N−ベタイン、1−[5−(2−メトキシフェニル)ペンチリデン]−3−オキソピラゾリジン N,N−ベタイン、1−[5−(3−メトキシフェニル)ペンチリデン]−3−オキソピラゾリジン N,N−ベタイン、1−[5−(4−メトキシフェニル)ペンチリデン]−3−オキソピラゾリジン N,N−ベタイン、1−[2−(2−エトキシフェニル)エチリデン]−3−オキソピラゾリジン N,N−ベタイン、1−[2−(3−エトキシフェニル)エチリデン]−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−エトキシフェニル)エチリデン]−3−オキソピラゾリジン N,N−ベタイン、1−[3−(2−エトキシフェニル)プロピリデン]−3−オキソピラゾリジン N,N−ベタイン、1−[3−(3−エトキシフェニル)プロピリデン]−3−オキソピラゾリジン N,N−ベタイン、1−[3−(4−エトキシフェニル)プロピリデン]−3−オキソピラゾリジン N,N−ベタイン、1−[4−(2−エトキシフェニル)ブチリデン]−3−オキソピラゾリジン N,N−ベタイン、1−[4−(3−エトキシフェニル)ブチリデン]−3−オキソピラゾリジン N,N−ベタイン、1−[4−(4−エトキシフェニル)ブチリデン]−3−オキソピラゾリジン N,N−ベタイン、1−[5−(2−エトキシフェニル)ペンチリデン]−3−オキソピラゾリジン N,N−ベタイン、1−[5−(3−エトキシフェニル)ペンチリデン]−3−オキソピラゾリジン N,N−ベタイン、1−[5−(4−エトキシフェニル)ペンチリデン]−3−オキソピラゾリジン N,N−ベタイン、1−[2−(2−フルオロフェニル)エチリデン]−3−オキソピラゾリジン N,N−ベタイン、1−[2−(3−フルオロフェニル)エチリデン]−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−フルオロフェニル)エチリデン]−3−オキソピラゾリジン N,N−ベタイン、1−[3−(2−フルオロフェニル)プロピリデン]−3−オキソピラゾリジン N,N−ベタイン、1−[3−(3−フルオロフェニル)プロピリデン]−3−オキソピラゾリジン N,N−ベタイン、1−[3−(4−フルオロフェニル)プロピリデン]−3−オキソピラゾリジン N,N−ベタイン、1−[4−(2−フルオロフェニル)ブチリデン]−3−オキソピラゾリジン N,N−ベタイン、1−[4−(3−フルオロフェニル)ブチリデン]−3−オキソピラゾリジン N,N−ベタイン、1−[4−(4−フルオロフェニル)ブチリデン]−3−オキソピラゾリジン N,N−ベタイン、1−[5−(2−フルオロフェニル)ペンチリデン]−3−オキソピラゾリジン N,N−ベタイン、1−[5−(3−フルオロフェニル)ペンチリデン]−3−オキソピラゾリジン N,N−ベタイン、1−[5−(4−フルオロフェニル)ペンチリデン]−3−オキソピラゾリジン N,N−ベタイン、1−[2−(2−クロロフェニル)エチリデン]−3−オキソピラゾリジン N,N−ベタイン、1−[2−(3−クロロフェニル)エチリデン]−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−クロロフェニル)エチリデン]−3−オキソピラゾリジン N,N−ベタイン、1−[3−(2−クロロフェニル)プロピリデン]−3−オキソピラゾリジン N,N−ベタイン、1−[3−(3−クロロフェニル)プロピリデン]−3−オキソピラゾリジン N,N−ベタイン、1−[3−(4−クロロフェニル)プロピリデン]−3−オキソピラゾリジン N,N−ベタイン、1−[4−(2−クロロフェニル)ブチリデン]−3−オキソピラゾリジン N,N−ベタイン、1−[4−(3−クロロフェニル)ブチリデン]−3−オキソピラゾリジン N,N−ベタイン、1−[4−(4−クロロフェニル)ブチリデン]−3−オキソピラゾリジン N,N−ベタイン、1−[5−(2−クロロフェニル)ペンチリデン]−3−オキソピラゾリジン N,N−ベタイン、1−[5−(3−クロロフェニル)ペンチリデン]−3−オキソピラゾリジン N,N−ベタイン、1−[5−(4−クロロフェニル)ペンチリデン]−3−オキソピラゾリジン N,N−ベタイン、1−[2−(2−ブロモフェニル)エチリデン]−3−オキソピラゾリジン N,N−ベタイン、1−[2−(3−ブロモフェニル)エチリデン]−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−ブロモフェニル)エチリデン]−3−オキソピラゾリジン N,N−ベタイン、1−[3−(2−ブロモフェニル)プロピリデン]−3−オキソピラゾリジン N,N−ベタイン、1−[3−(3−ブロモフェニル)プロピリデン]−3−オキソピラゾリジン N,N−ベタイン、1−[3−(4−ブロモフェニル)プロピリデン]−3−オキソピラゾリジン N,N−ベタイン、1−[4−(2−ブロモフェニル)ブチリデン]−3−オキソピラゾリジン N,N−ベタイン、1−[4−(3−ブロモフェニル)ブチリデン]−3−オキソピラゾリジン N,N−ベタイン、1−[4−(4−ブロモフェニル)ブチリデン]−3−オキソピラゾリジン N,N−ベタイン、1−[5−(2−ブロモフェニル)ペンチリデン]−3−オキソピラゾリジン N,N−ベタイン、1−[5−(3−ブロモフェニル)ペンチリデン]−3−オキソピラゾリジン N,N−ベタイン、1−[5−(4−ブロモフェニル)ペンチリデン]−3−オキソピラゾリジン N,N−ベタイン、1−[2−(2−シアノフェニル)エチリデン]−3−オキソピラゾリジン N,N−ベタイン、1−[2−(3−シアノフェニル)エチリデン]−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−シアノフェニル)エチリデン]−3−オキソピラゾリジン N,N−ベタイン、1−[3−(2−シアノフェニル)プロピリデン]−3−オキソピラゾリジン N,N−ベタイン、1−[3−(3−シアノフェニル)プロピリデン]−3−オキソピラゾリジン N,N−ベタイン、1−[3−(4−シアノフェニル)プロピリデン]−3−オキソピラゾリジン N,N−ベタイン、1−[4−(2−シアノフェニル)ブチリデン]−3−オキソピラゾリジン N,N−ベタイン、1−[4−(3−シアノフェニル)ブチリデン]−3−オキソピラゾリジン N,N−ベタイン、1−[4−(4−シアノフェニル)ブチリデン]−3−オキソピラゾリジン N,N−ベタイン、1−[5−(2−シアノフェニル)ペンチリデン]−3−オキソピラゾリジン N,N−ベタイン、1−[5−(3−シアノフェニル)ペンチリデン]−3−オキソピラゾリジン N,N−ベタイン、1−[5−(4−シアノフェニル)ペンチリデン]−3−オキソピラゾリジン N,N−ベタイン、1−[2−(2−ニトロフェニル)エチリデン]−3−オキソピラゾリジン N,N−ベタイン、1−[2−(3−ニトロフェニル)エチリデン]−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−ニトロフェニル)エチリデン]−3−オキソピラゾリジン N,N−ベタイン、1−[3−(2−ニトロフェニル)プロピリデン]−3−オキソピラゾリジン N,N−ベタイン、1−[3−(3−ニトロフェニル)プロピリデン]−3−オキソピラゾリジン N,N−ベタイン、1−[3−(4−ニトロフェニル)プロピリデン]−3−オキソピラゾリジン N,N−ベタイン、1−[4−(2−ニトロフェニル)ブチリデン]−3−オキソピラゾリジン N,N−ベタイン、1−[4−(3−ニトロフェニル)ブチリデン]−3−オキソピラゾリジン N,N−ベタイン、1−[4−(4−ニトロフェニル)ブチリデン]−3−オキソピラゾリジン N,N−ベタイン、1−[5−(2−ニトロフェニル)ペンチリデン]−3−オキソピラゾリジン N,N−ベタイン、1−[5−(3−ニトロフェニル)ペンチリデン]−3−オキソピラゾリジン N,N−ベタイン、1−[5−(4−ニトロフェニル)ペンチリデン]−3−オキソピラゾリジン N,N−ベタ
イン等をあげることができる。
Specific examples of the N, N-betaine derivative represented by the general formula (2) of the present invention include a 3-oxopyrazoline skeleton, and R 3 is an arylalkyl group which may have a substituent. For example, 1- (2-phenylethylidene) -3-oxopyrazolidine N, N-betaine, 1- (3-phenylpropylidene) -3-oxopyrazolidine N, N-betaine, 1- (4 -Phenylbutylidene) -3-oxopyrazolidine N, N-betaine, 1- (5-phenylpentylidene) -3-oxopyrazolidine N, N-betaine, 1- (6-phenylhexylidene) -3-Oxopyrazolidine N, N-betaine, 1- [2- (2-methylphenyl) ethylidene] -3-oxopyrazolidine N, N-betaine, 1- [2- (3-methylphenyl) Echi Ridene] -3-oxopyrazolidine N, N-betaine, 1- [2- (4-methylphenyl) ethylidene] -3-oxopyrazolidine N, N-betaine, 1- [3- (2-methyl) Phenyl) propylidene] -3-oxopyrazolidine N, N-betaine, 1- [3- (3-methylphenyl) propylidene] -3-oxopyrazolidine N, N-betaine, 1- [3- (4 -Methylphenyl) propylidene] -3-oxopyrazolidine N, N-betaine, 1- [4- (2-methylphenyl) butylidene] -3-oxopyrazolidine N, N-betaine, 1- [4- (3-methylphenyl) butylidene] -3-oxopyrazolidine N, N-betaine, 1- [4- (4-methylphenyl) butylidene] -3-oxopyrazolidine N, N-betaine, 1 [5- (2-methylphenyl) pentylidene] -3-oxopyrazolidine N, N-betaine, 1- [5- (3-methylphenyl) pentylidene] -3-oxopyrazolidine N, N-betaine, 1- [5- (4-Methylphenyl) pentylidene] -3-oxopyrazolidine N, N-betaine, 1- [2- (2-ethylphenyl) ethylidene] -3-oxopyrazolidine N, N- Betaine, 1- [2- (3-ethylphenyl) ethylidene] -3-oxopyrazolidine N, N-betaine, 1- [2- (4-ethylphenyl) ethylidene] -3-oxopyrazolidine N, N-betaine, 1- [3- (2-ethylphenyl) propylidene] -3-oxopyrazolidine N, N-betaine, 1- [3- (3-ethylphenyl) propylidene] -3-O Sopyrazolidine N, N-betaine, 1- [3- (4-ethylphenyl) propylidene] -3-oxopyrazolidine N, N-betaine, 1- [4- (2-ethylphenyl) butylidene] -3-oxo Pyrazolidine N, N-betaine, 1- [4- (3-ethylphenyl) butylidene] -3-oxopyrazolidine N, N-betaine, 1- [4- (4-ethylphenyl) butylidene] -3 -Oxopyrazolidine N, N-betaine, 1- [5- (2-ethylphenyl) pentylidene] -3-oxopyrazolidine N, N-betaine, 1- [5- (3-ethylphenyl) pentylidene] -3-oxopyrazolidine N, N-betaine, 1- [5- (4-ethylphenyl) pentylidene] -3-oxopyrazolidine N, N-betaine, 1- [2- (2-me Xylphenyl) ethylidene] -3-oxopyrazolidine N, N-betaine, 1- [2- (3-methoxyphenyl) ethylidene] -3-oxopyrazolidine N, N-betaine, 1- [2- (4 -Methoxyphenyl) ethylidene] -3-oxopyrazolidine N, N-betaine, 1- [3- (2-methoxyphenyl) propylidene] -3-oxopyrazolidine N, N-betaine, 1- [3- (3-methoxyphenyl) propylidene] -3-oxopyrazolidine N, N-betaine, 1- [3- (4-methoxyphenyl) propylidene] -3-oxopyrazolidine N, N-betaine, 1- [ 4- (2-methoxyphenyl) butylidene] -3-oxopyrazolidine N, N-betaine, 1- [4- (3-methoxyphenyl) butylidene] -3-oxo Lazolidine N, N-betaine, 1- [4- (4-methoxyphenyl) butylidene] -3-oxopyrazolidine N, N-betaine, 1- [5- (2-methoxyphenyl) pentylidene] -3-oxo Pyrazolidine N, N-betaine, 1- [5- (3-methoxyphenyl) pentylidene] -3-oxopyrazolidine N, N-betaine, 1- [5- (4-methoxyphenyl) pentylidene] -3 -Oxopyrazolidine N, N-betaine, 1- [2- (2-ethoxyphenyl) ethylidene] -3-oxopyrazolidine N, N-betaine, 1- [2- (3-ethoxyphenyl) ethylidene] -3-oxopyrazolidine N, N-betaine, 1- [2- (4-ethoxyphenyl) ethylidene] -3-oxopyrazolidine N, N-betaine, 1- [3- (2-Ethoxyphenyl) propylidene] -3-oxopyrazolidine N, N-betaine, 1- [3- (3-ethoxyphenyl) propylidene] -3-oxopyrazolidine N, N-betaine, 1- [ 3- (4-Ethoxyphenyl) propylidene] -3-oxopyrazolidine N, N-betaine, 1- [4- (2-ethoxyphenyl) butylidene] -3-oxopyrazolidine N, N-betaine, 1 -[4- (3-Ethoxyphenyl) butylidene] -3-oxopyrazolidine N, N-betaine, 1- [4- (4-ethoxyphenyl) butylidene] -3-oxopyrazolidine N, N-betaine , 1- [5- (2-ethoxyphenyl) pentylidene] -3-oxopyrazolidine N, N-betaine, 1- [5- (3-ethoxyphenyl) pentylidene] -3-oxopyrazolidine N, N-betaine, 1- [5- (4-ethoxyphenyl) pentylidene] -3-oxopyrazolidine N, N-betaine, 1- [2- (2-fluorophenyl) Ethylidene] -3-oxopyrazolidine N, N-betaine, 1- [2- (3-fluorophenyl) ethylidene] -3-oxopyrazolidine N, N-betaine, 1- [2- (4-fluoro Phenyl) ethylidene] -3-oxopyrazolidine N, N-betaine, 1- [3- (2-fluorophenyl) propylidene] -3-oxopyrazolidine N, N-betaine, 1- [3- (3 -Fluorophenyl) propylidene] -3-oxopyrazolidine N, N-betaine, 1- [3- (4-fluorophenyl) propylidene] -3-oxopyrazolidine N, N-beta 1- [4- (2-fluorophenyl) butylidene] -3-oxopyrazolidine N, N-betaine, 1- [4- (3-fluorophenyl) butylidene] -3-oxopyrazolidine N, N-betaine, 1- [4- (4-fluorophenyl) butylidene] -3-oxopyrazolidine N, N-betaine, 1- [5- (2-fluorophenyl) pentylidene] -3-oxopyrazolidine N, N-betaine, 1- [5- (3-fluorophenyl) pentylidene] -3-oxopyrazolidine N, N-betaine, 1- [5- (4-fluorophenyl) pentylidene] -3-oxopyrazine Zolidine N, N-betaine, 1- [2- (2-chlorophenyl) ethylidene] -3-oxopyrazolidine N, N-betaine, 1- [2- (3-chlorophenyl) ethyl Den] -3-oxopyrazolidine N, N-betaine, 1- [2- (4-chlorophenyl) ethylidene] -3-oxopyrazolidine N, N-betaine, 1- [3- (2-chlorophenyl) Propyridene] -3-oxopyrazolidine N, N-betaine, 1- [3- (3-chlorophenyl) propylidene] -3-oxopyrazolidine N, N-betaine, 1- [3- (4-chlorophenyl) Propyridene] -3-oxopyrazolidine N, N-betaine, 1- [4- (2-chlorophenyl) butylidene] -3-oxopyrazolidine N, N-betaine, 1- [4- (3-chlorophenyl) Butylidene] -3-oxopyrazolidine N, N-betaine, 1- [4- (4-chlorophenyl) butylidene] -3-oxopyrazolidine N, N-betaine, 1- 5- (2-chlorophenyl) pentylidene] -3-oxopyrazolidine N, N-betaine, 1- [5- (3-chlorophenyl) pentylidene] -3-oxopyrazolidine N, N-betaine, 1- [ 5- (4-chlorophenyl) pentylidene] -3-oxopyrazolidine N, N-betaine, 1- [2- (2-bromophenyl) ethylidene] -3-oxopyrazolidine N, N-betaine, 1- [2- (3-bromophenyl) ethylidene] -3-oxopyrazolidine N, N-betaine, 1- [2- (4-bromophenyl) ethylidene] -3-oxopyrazolidine N, N-betaine, 1- [3- (2-bromophenyl) propylidene] -3-oxopyrazolidine N, N-betaine, 1- [3- (3-bromophenyl) propylidene] -3-oxy Pyrazolidine N, N-betaine, 1- [3- (4-bromophenyl) propylidene] -3-oxopyrazolidine N, N-betaine, 1- [4- (2-bromophenyl) butylidene] -3-oxo Pyrazolidine N, N-betaine, 1- [4- (3-bromophenyl) butylidene] -3-oxopyrazolidine N, N-betaine, 1- [4- (4-bromophenyl) butylidene] -3 -Oxopyrazolidine N, N-betaine, 1- [5- (2-bromophenyl) pentylidene] -3-oxopyrazolidine N, N-betaine, 1- [5- (3-bromophenyl) pentylidene] -3-oxopyrazolidine N, N-betaine, 1- [5- (4-bromophenyl) pentylidene] -3-oxopyrazolidine N, N-betaine, 1- [2- (2-sia Nophenyl) ethylidene] -3-oxopyrazolidine N, N-betaine, 1- [2- (3-cyanophenyl) ethylidene] -3-oxopyrazolidine N, N-betaine, 1- [2- (4 -Cyanophenyl) ethylidene] -3-oxopyrazolidine N, N-betaine, 1- [3- (2-cyanophenyl) propylidene] -3-oxopyrazolidine N, N-betaine, 1- [3- (3-Cyanophenyl) propylidene] -3-oxopyrazolidine N, N-betaine, 1- [3- (4-cyanophenyl) propylidene] -3-oxopyrazolidine N, N-betaine, 1- [ 4- (2-cyanophenyl) butylidene] -3-oxopyrazolidine N, N-betaine, 1- [4- (3-cyanophenyl) butylidene] -3-oxopyrazolidine N, -Betaine, 1- [4- (4-cyanophenyl) butylidene] -3-oxopyrazolidine N, N-betaine, 1- [5- (2-cyanophenyl) pentylidene] -3-oxopyrazolidine N , N-betaine, 1- [5- (3-cyanophenyl) pentylidene] -3-oxopyrazolidine N, N-betaine, 1- [5- (4-cyanophenyl) pentylidene] -3-oxopyrazoidine Lysine N, N-betaine, 1- [2- (2-nitrophenyl) ethylidene] -3-oxopyrazolidine N, N-betaine, 1- [2- (3-nitrophenyl) ethylidene] -3-oxo Pyrazolidine N, N-betaine, 1- [2- (4-nitrophenyl) ethylidene] -3-oxopyrazolidine N, N-betaine, 1- [3- (2-nitrophenyl) propylene ] -3-oxopyrazolidine N, N-betaine, 1- [3- (3-nitrophenyl) propylidene] -3-oxopyrazolidine N, N-betaine, 1- [3- (4-nitro Phenyl) propylidene] -3-oxopyrazolidine N, N-betaine, 1- [4- (2-nitrophenyl) butylidene] -3-oxopyrazolidine N, N-betaine, 1- [4- (3 -Nitrophenyl) butylidene] -3-oxopyrazolidine N, N-betaine, 1- [4- (4-nitrophenyl) butylidene] -3-oxopyrazolidine N, N-betaine, 1- [5- (2-Nitrophenyl) pentylidene] -3-oxopyrazolidine N, N-betaine, 1- [5- (3-nitrophenyl) pentylidene] -3-oxopyrazolidine N, N-betaine, 1- 5- (4-nitrophenyl) pentylidene] -3-oxo pyrazolidine N, can be mentioned N- betaine.

本発明の一般式(2)で表されるN,N−ベタイン誘導体として、4,4−ジメチル−3−オキソピラゾリン骨格を有し、Rがメチル基、エチル基、炭素数3〜10の直鎖、分岐若しくは環式のアルキル基であるものとしては、具体的には例えば、1−(エチリデン)−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(n−プロピリデン)−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(n−ブチリデン)−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(2−メチルプロピリデン)−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(n−ペンチレリデン)−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(2,2−ジメチルプロピリデン)−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(n−ヘキシリデン)−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(n−ヘプチリデン)−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(シクロヘキシルメチリデン)−4,4−ジメチル−3−オキソピラゾリン N,N−ベタイン、1−(n−オクチリデン)−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(n−ノナニリデン)−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(n−デシリデン)−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(n−ウンデシリデン)−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン等を挙げることができる。 The N, N-betaine derivative represented by the general formula (2) of the present invention has a 4,4-dimethyl-3-oxopyrazoline skeleton, and R 3 is a methyl group, an ethyl group, a straight chain having 3 to 10 carbon atoms. Specific examples of the chain, branched or cyclic alkyl group include 1- (ethylidene) -4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- (n- Propylidene) -4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- (n-butylidene) -4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- ( 2-methylpropylidene) -4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- (n-pentyllidene) -4,4-dimethyl-3-oxopyrazolidine N, N-betaine , 1- (2,2-dimension Rupropylidene) -4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- (n-hexylidene) -4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- ( n-heptylidene) -4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- (cyclohexylmethylidene) -4,4-dimethyl-3-oxopyrazolin N, N-betaine, 1- (n -Octylidene) -4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- (n-nonanilidene) -4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- (N-decylidene) -4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- (n-undecylidene) -4,4-dimethyl-3-oxopyrazolidine N, N- Examples include betaine.

本発明の一般式(2)で表されるN,N−ベタイン誘導体として、4,4−ジメチル−3−オキソピラゾリン骨格を有し、Rが置換基を有しても良いフェニル基であるものとしては、具体的には例えば、1−ベンジリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(2−メチルフェニル)メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(3−メチルフェニル)メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(4−メチルフェニル)メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(2−エチルフェニル)メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(3−エチルフェニル)メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(4−エチルフェニル)メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(2−n−プロピルフェニル)メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(3−n−プロピルフェニル)メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(4−n−プロピルフェニル)メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(2−iso−プロピルフェニル)メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(3−iso−プロピルフェニル)メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(4−iso−プロピルフェニル)メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(2−n−ブチルフェニル)メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(3−n−ブチルフェニル)メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(4−n−ブチルフェニル)メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(2−iso−ブチルフェニル)メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(3−iso−ブチルフェニル)メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(4−iso−ブチルフェニル)メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(2−tert−ブチルフェニル)メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(3−tert−ブチルフェニル)メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(4−tert−ブチルフェニル)メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(4−n−ペンチルフェニル)メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(4−n−ヘキシルフェニル)メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(4−n−ヘプチルフェニル)メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(4−n−オクチルフェニル)メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(4−n−ノニルフェニル)メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(4−n−デシルフェニル)メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(2−メトキシフェニル)メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(3−メトキシフェニル)メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(4−メトキシフェニル)メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(2−エトキシフェニル)メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(3−エトキシフェニル)メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(4−エトキシフェニル)メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(2−n−プロポキシフェニル)メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(3−n−プロポキシフェニル)メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(4−n−プロポキシフェニル)メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(2−iso−プロポキシフェニル)メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(3−iso−プロポキシフェニル)メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(4−iso−プロポキシフェニル)メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(2−n−ブトキシフェニル)メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(3−n−ブトキシフェニル)メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(4−n−ブトキシフェニル)メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(2−iso−ブトキシフェニル)メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(3−iso−ブトキシフェニル)メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(4−iso−ブトキシフェニル)メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(2−tert−ブトキシフェニル)メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(3−tert−ブトキシフェニル)メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(4−tert−ブトキシフェニル)メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(4−n−ペントキシフェニル)メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(4−n−ヘキシルオキシフェニル)メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(4−n−ヘプチルオキシフェニル)メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(4−n−オクチルオキシフェニル)メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(4−n−ノニルオキシフェニル)メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(4−n−デシルオキシフェニル)メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(2−フルオロフェニル)メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(3−フルオロフェニル)メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(4−フルオロフェニル)メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(2−クロロフェニル)メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(3−クロロフェニル)メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(4−クロロフェニル)メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(2−ブロモフェニル)メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(3−ブロモフェニル)メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(4−ブロモフェニル)メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(2−シアノフェニル)メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(3−シアノフェニル)メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(4−シアノフェニル)メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(2−ニトロフェニル)メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(3−ニトロフェニル)メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(4−ニトロフェニル)メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン等を挙げることができる。 The N, N-betaine derivative represented by the general formula (2) of the present invention has a 4,4-dimethyl-3-oxopyrazoline skeleton, and R 3 is a phenyl group which may have a substituent. Specifically, for example, 1-benzylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- (2-methylphenyl) methylidene-4,4-dimethyl-3-oxo Pyrazolidine N, N-betaine, 1- (3-methylphenyl) methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- (4-methylphenyl) methylidene-4,4 -Dimethyl-3-oxopyrazolidine N, N-betaine, 1- (2-ethylphenyl) methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- (3-ethylphen Nyl) methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- (4-ethylphenyl) methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- (2-n-propylphenyl) methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- (3-n-propylphenyl) methylidene-4,4-dimethyl-3- Oxopyrazolidine N, N-betaine, 1- (4-n-propylphenyl) methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- (2-iso-propylphenyl) Methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- (3-iso-propylphenyl) methylidene-4,4-dimethyl-3-oxo Lazolidine N, N-betaine, 1- (4-iso-propylphenyl) methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- (2-n-butylphenyl) methylidene-4 , 4-Dimethyl-3-oxopyrazolidine N, N-betaine, 1- (3-n-butylphenyl) methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- ( 4-n-Butylphenyl) methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- (2-iso-butylphenyl) methylidene-4,4-dimethyl-3-oxopyrazo Lysine N, N-betaine, 1- (3-iso-butylphenyl) methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- (4-iso- Tylphenyl) methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- (2-tert-butylphenyl) methylidene-4,4-dimethyl-3-oxopyrazolidine N, N- Betaine, 1- (3-tert-butylphenyl) methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- (4-tert-butylphenyl) methylidene-4,4-dimethyl- 3-oxopyrazolidine N, N-betaine, 1- (4-n-pentylphenyl) methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- (4-n-hexyl) Phenyl) methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- (4-n-heptylphenyl) methylidene-4,4-dimethyl Tyl-3-oxopyrazolidine N, N-betaine, 1- (4-n-octylphenyl) methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- (4-n -Nonylphenyl) methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- (4-n-decylphenyl) methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- (2-methoxyphenyl) methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- (3-methoxyphenyl) methylidene-4,4-dimethyl-3- Oxopyrazolidine N, N-betaine, 1- (4-methoxyphenyl) methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- (2-ethoxyphenyl) Enyl) methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- (3-ethoxyphenyl) methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- (4-Ethoxyphenyl) methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- (2-n-propoxyphenyl) methylidene-4,4-dimethyl-3-oxopyra Zolidine N, N-betaine, 1- (3-n-propoxyphenyl) methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- (4-n-propoxyphenyl) methylidene- 4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- (2-iso-propoxyphenyl) methylidene-4,4-dimethyl-3-oxy Pyrazolidine N, N-betaine, 1- (3-iso-propoxyphenyl) methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- (4-iso-propoxyphenyl) methylidene-4 , 4-Dimethyl-3-oxopyrazolidine N, N-betaine, 1- (2-n-butoxyphenyl) methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- ( 3-n-butoxyphenyl) methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- (4-n-butoxyphenyl) methylidene-4,4-dimethyl-3-oxopyrazo Lysine N, N-betaine, 1- (2-iso-butoxyphenyl) methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1 (3-iso-butoxyphenyl) methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- (4-iso-butoxyphenyl) methylidene-4,4-dimethyl-3-oxopyra Zolidine N, N-betaine, 1- (2-tert-butoxyphenyl) methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- (3-tert-butoxyphenyl) methylidene- 4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- (4-tert-butoxyphenyl) methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- (4-n-pentoxyphenyl) methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- (4-n-hexylo) Ciphenyl) methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- (4-n-heptyloxyphenyl) methylidene-4,4-dimethyl-3-oxopyrazolidine N, N -Betaine, 1- (4-n-octyloxyphenyl) methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- (4-n-nonyloxyphenyl) methylidene-4,4 -Dimethyl-3-oxopyrazolidine N, N-betaine, 1- (4-n-decyloxyphenyl) methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- (2 -Fluorophenyl) methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- (3-fluorophenyl) methylidene-4,4-dimethyl Lu-3-oxopyrazolidine N, N-betaine, 1- (4-fluorophenyl) methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- (2-chlorophenyl) methylidene -4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- (3-chlorophenyl) methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- (4 -Chlorophenyl) methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- (2-bromophenyl) methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine 1- (3-bromophenyl) methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- (4-bromophenyl) methylidene-4 , 4-Dimethyl-3-oxopyrazolidine N, N-betaine, 1- (2-cyanophenyl) methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- (3- Cyanophenyl) methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- (4-cyanophenyl) methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine 1- (2-nitrophenyl) methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- (3-nitrophenyl) methylidene-4,4-dimethyl-3-oxopyrazo Examples include lysine N, N-betaine and 1- (4-nitrophenyl) methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine.

本発明の一般式(2)で表されるN,N−ベタイン誘導体として、4,4−ジメチル−3−オキソピラゾリン骨格を有し、Rが置換基を有しても良い1−ナフチル基であるものとしては、具体的には例えば、1−(1−ナフチルメチリデン)−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−メチルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(3−メチルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−メチルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(5−メチルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−メチルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(7−メチルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−メチルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−エチルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(3−エチルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−エチルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(5−エチルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−エチルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(7−エチルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−エチルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−n−プロピルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(3−n−プロピルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−n−プロピルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(5−n−プロピルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−n−プロピルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(7−n−プロピルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−n−プロピルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−iso−プロピルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(3−iso−プロピルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−iso−プロピルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(5−iso−プロピルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−iso−プロピルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(7−iso−プロピルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−iso−プロピルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−n−ブチルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(3−n−ブチルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−n−ブチルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(5−n−ブチルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−n−ブチルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(7−n−ブチルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−n−ブチルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−iso−ブチルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(3−iso−ブチルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−iso−ブチルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(5−iso−ブチルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−iso−ブチルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(7−iso−ブチルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−iso−ブチルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−tert−ブチルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(3−tert−ブチルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−tert−ブチルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(5−tert−ブチルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−tert−ブチルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(7−tert−ブチルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−tert−ブチルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−n−ペンチルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−n−ペンチルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−n−ペンチルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−n−ペンチルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−n−ヘキシルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−n−ヘキシルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−n−ヘキシルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−n−ヘキシルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−n−ヘプチルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−n−ヘプチルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−n−ヘプチルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−n−ヘプチルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−n−オクチルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−n−オクチルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−n−オクチルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−n−オクチルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−n−ノニルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−n−ノニルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−n−ノニルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−n−ノニルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−n−デシルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−n−デシルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−n−デシルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−n−デシルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−メトキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(3−メトキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−メトキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(5−メトキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−メトキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(7−メトキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−メトキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−エトキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(3−エトキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−エトキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(5−エトキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−エトキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(7−エトキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−エトキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−n−プロポキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(3−n−プロポキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−n−プロポキシナフチル)]メチリデン−4,4−ジメチル−3−
オキソピラゾリジン N,N−ベタイン、1−[1−(5−n−プロポキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−n−プロポキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(7−n−プロポキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−n−プロポキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−iso−プロポキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(3−iso−プロポキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−iso−プロポキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(5−iso−プロポキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−iso−プロポキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(7−iso−プロポキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−iso−プロポキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−n−ブトキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(3−n−ブトキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−n−ブトキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(5−n−ブトキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−n−ブトキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(7−n−ブトキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−n−ブトキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−iso−ブトキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(3−iso−ブトキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−iso−ブトキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(5−iso−ブトキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−iso−ブトキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(7−iso−ブトキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−iso−ブトキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−tert−ブトキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(3−tert−ブトキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−tert−ブトキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(5−tert−ブトキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−tert−ブトキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(7−tert−ブトキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−tert−ブトキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−n−ペントキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−n−ペントキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−n−ペントキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−n−ペントキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−n−ヘキシルオキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−n−ヘキシルオキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−n−ヘキシルオキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−n−ヘキシルオキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−n−ヘプチルオキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−n−ヘプチルオキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−n−ヘプチルオキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−n−ヘプチルオキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−n−オクチルオキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−n−オクチルオキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−n−オクチルオキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−n−オクチルオキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−n−ノニルオキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−n−ノニルオキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−n−ノニルオキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−n−ノニルオキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−n−デシルオキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−n−デシルオキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−n−デシルオキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−n−デシルオキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−フルオロナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(3−フルオロナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−フルオロナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(5−フルオロナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−フルオロナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(7−フルオロナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−フルオロナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−クロロナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(3−クロロナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−クロロナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(5−クロロナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−クロロナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(7−クロロナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−クロロナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−ブロモナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(3−ブロモナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−ブロモナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(5−ブロモナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−ブロモナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(7−ブロモナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−ブロモナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−シアノナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(3−シアノナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−シアノナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(5−シアノナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−シアノナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(7−シアノナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−シアノナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−ニトロナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(3−ニトロナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−ニトロナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(5−ニトロナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−ニトロナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(7−ニトロナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−ニトロナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリ
ジン N,N−ベタイン等を挙げることができる。
The N, N-betaine derivative represented by the general formula (2) of the present invention is a 1-naphthyl group having a 4,4-dimethyl-3-oxopyrazoline skeleton, and R 3 may have a substituent. Specific examples include 1- (1-naphthylmethylidene) -4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (2-methylnaphthyl), for example. ] Methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (3-methylnaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N -Betaine, 1- [1- (4-methylnaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (5-methylnaphthyl)] methylidene-4 , 4-Dimethyl-3-Oki Pyrazolidine N, N-betaine, 1- [1- (6-methylnaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (7-methylnaphthyl) ] Methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (8-methylnaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N -Betaine, 1- [1- (2-ethylnaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (3-ethylnaphthyl)] methylidene-4 , 4-Dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (4-ethylnaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1 − [ -(5-Ethylnaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (6-ethylnaphthyl)] methylidene-4,4-dimethyl-3- Oxopyrazolidine N, N-betaine, 1- [1- (7-ethylnaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (8- Ethyl naphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (2-n-propylnaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazine Zolidine N, N-betaine, 1- [1- (3-n-propylnaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (4- n-propyl naphthy L)] Methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (5-n-propylnaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazo Lysine N, N-betaine, 1- [1- (6-n-propylnaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (7-n -Propylnaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (8-n-propylnaphthyl)] methylidene-4,4-dimethyl-3-oxo Pyrazolidine N, N-betaine, 1- [1- (2-iso-propylnaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (3 -Iso-propyl Butyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (4-iso-propylnaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazo Lysine N, N-betaine, 1- [1- (5-iso-propylnaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (6-iso -Propylnaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (7-iso-propylnaphthyl)] methylidene-4,4-dimethyl-3-oxo Pyrazolidine N, N-betaine, 1- [1- (8-iso-propylnaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- 2-n-butylnaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (3-n-butylnaphthyl)] methylidene-4,4-dimethyl- 3-oxopyrazolidine N, N-betaine, 1- [1- (4-n-butylnaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1 -(5-n-Butylnaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (6-n-butylnaphthyl)] methylidene-4,4- Dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (7-n-butylnaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (8-n-butyl Naphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (2-iso-butylnaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazo Lysine N, N-betaine, 1- [1- (3-iso-butylnaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (4-iso -Butylnaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (5-iso-butylnaphthyl)] methylidene-4,4-dimethyl-3-oxo Pyrazolidine N, N-betaine, 1- [1- (6-iso-butylnaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (7 -Is -Butylnaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (8-iso-butylnaphthyl)] methylidene-4,4-dimethyl-3-oxo Pyrazolidine N, N-betaine, 1- [1- (2-tert-butylnaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (3 -Tert-butylnaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (4-tert-butylnaphthyl)] methylidene-4,4-dimethyl-3 -Oxopyrazolidine N, N-betaine, 1- [1- (5-tert-butylnaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1 [1- (6-tert-butylnaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (7-tert-butylnaphthyl)] methylidene-4, 4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (8-tert-butylnaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (2-n-pentylnaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (4-n-pentylnaphthyl)] methylidene- 4,4-Dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (6-n-pentylnaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N- Solid In, 1- [1- (8-n-pentylnaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (2-n-hexylnaphthyl)] Methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (4-n-hexylnaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (6-n-hexylnaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (8-n-hexylnaphthyl) )] Methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (2-n-heptylnaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-Betai , 1- [1- (4-n-heptylnaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (6-n-heptylnaphthyl)] methylidene -4,4-Dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (8-n-heptylnaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N -Betaine, 1- [1- (2-n-octylnaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (4-n-octylnaphthyl) ] Methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (6-n-octylnaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N , N-betaine 1- [1- (8-n-octylnaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (2-n-nonylnaphthyl)] methylidene- 4,4-Dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (4-n-nonylnaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N- Betaine, 1- [1- (6-n-nonylnaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (8-n-nonylnaphthyl)] Methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (2-n-decylnaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- ( 4-n-decylnaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (6-n-decylnaphthyl)] methylidene-4,4-dimethyl- 3-oxopyrazolidine N, N-betaine, 1- [1- (8-n-decylnaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1 -(2-Methoxynaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (3-methoxynaphthyl)] methylidene-4,4-dimethyl-3- Oxopyrazolidine N, N-betaine, 1- [1- (4-methoxynaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (5- Methoxynaphthyl ] Methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (6-methoxynaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N -Betaine, 1- [1- (7-methoxynaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (8-methoxynaphthyl)] methylidene-4 , 4-Dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (2-ethoxynaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1 -[1- (3-Ethoxynaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (4-ethoxynaphthyl)] methylidene-4,4-di Tyl-3-oxopyrazolidine N, N-betaine, 1- [1- (5-ethoxynaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1 -(6-Ethoxynaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (7-ethoxynaphthyl)] methylidene-4,4-dimethyl-3- Oxopyrazolidine N, N-betaine, 1- [1- (8-ethoxynaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (2- n-propoxynaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (3-n-propoxynaphthyl)] methylidene-4,4-dimethyl-3- Oki Sopyrazolidine N, N-betaine, 1- [1- (4-n-propoxynaphthyl)] methylidene-4,4-dimethyl-3-
Oxopyrazolidine N, N-betaine, 1- [1- (5-n-propoxynaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- ( 6-n-propoxynaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (7-n-propoxynaphthyl)] methylidene-4,4-dimethyl- 3-oxopyrazolidine N, N-betaine, 1- [1- (8-n-propoxynaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1 -(2-iso-propoxynaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (3-iso-propoxynaphthyl)] methylidene-4, -Dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (4-iso-propoxynaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1 -[1- (5-iso-propoxynaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (6-iso-propoxynaphthyl)] methylidene-4 , 4-Dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (7-iso-propoxynaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine 1- [1- (8-iso-propoxynaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (2-n-butoxy) Butyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (3-n-butoxynaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazo Lysine N, N-betaine, 1- [1- (4-n-butoxynaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (5-n -Butoxynaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (6-n-butoxynaphthyl)] methylidene-4,4-dimethyl-3-oxo Pyrazolidine N, N-betaine, 1- [1- (7-n-butoxynaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (8 -N-Butoxynaphth Til)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (2-iso-butoxynaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazo Lysine N, N-betaine, 1- [1- (3-iso-butoxynaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (4-iso -Butoxynaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (5-iso-butoxynaphthyl)] methylidene-4,4-dimethyl-3-oxo Pyrazolidine N, N-betaine, 1- [1- (6-iso-butoxynaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (7 iso-butoxynaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (8-iso-butoxynaphthyl)] methylidene-4,4-dimethyl-3- Oxopyrazolidine N, N-betaine, 1- [1- (2-tert-butoxynaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- ( 3-tert-butoxynaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (4-tert-butoxynaphthyl)] methylidene-4,4-dimethyl- 3-oxopyrazolidine N, N-betaine, 1- [1- (5-tert-butoxynaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N N-betaine, 1- [1- (6-tert-butoxynaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (7-tert-butoxynaphthyl) )] Methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (8-tert-butoxynaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (2-n-pentoxynaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (4-n -Pentoxynaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (6-n-pentoxynaphthyl)] methylidene-4,4-dimethyl-3 − Xopyrazolidine N, N-betaine, 1- [1- (8-n-pentoxynaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (2- n-hexyloxynaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (4-n-hexyloxynaphthyl)] methylidene-4,4-dimethyl- 3-oxopyrazolidine N, N-betaine, 1- [1- (6-n-hexyloxynaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [ 1- (8-n-hexyloxynaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (2-n-heptyloxynaphthyl)] methyl Den-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (4-n-heptyloxynaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N , N-betaine, 1- [1- (6-n-heptyloxynaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (8-n- Heptyloxynaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (2-n-octyloxynaphthyl)] methylidene-4,4-dimethyl-3- Oxopyrazolidine N, N-betaine, 1- [1- (4-n-octyloxynaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (6-n -Octyloxynaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (8-n-octyloxynaphthyl)] methylidene-4,4-dimethyl-3 -Oxopyrazolidine N, N-betaine, 1- [1- (2-n-nonyloxynaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1 -(4-n-nonyloxynaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (6-n-nonyloxynaphthyl)] methylidene-4, 4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (8-n-nonyloxynaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-beta In, 1- [1- (2-n-decyloxynaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (4-n-decyloxynaphthyl) )] Methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (6-n-decyloxynaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazo Lysine N, N-betaine, 1- [1- (8-n-decyloxynaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (2- Fluoronaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (3-fluoronaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, -Betaine, 1- [1- (4-fluoronaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (5-fluoronaphthyl)] methylidene-4 , 4-Dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (6-fluoronaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1 -[1- (7-Fluoronaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (8-fluoronaphthyl)] methylidene-4,4-dimethyl -3-oxopyrazolidine N, N-betaine, 1- [1- (2-chloronaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (3- Chloronaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (4-chloronaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (5-chloronaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (6-chloronaphthyl)] Methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (7-chloronaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N- Betaine, 1- [1- (8-chloronaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (2-bromonaphthyl)] methylidene-4, 4- Methyl-3-oxopyrazolidine N, N-betaine, 1- [1- (3-bromonaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1 -(4-Bromonaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (5-bromonaphthyl)] methylidene-4,4-dimethyl-3- Oxopyrazolidine N, N-betaine, 1- [1- (6-bromonaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (7- Bromonaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (8-bromonaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N Betaine, 1- [1- (2-cyanonaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (3-cyanonaphthyl)] methylidene-4, 4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (4-cyanonaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (5-cyanonaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (6-cyanonaphthyl)] methylidene-4,4-dimethyl- 3-oxopyrazolidine N, N-betaine, 1- [1- (7-cyanonaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- ( 8-cyanonaphth L)] Methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (2-nitronaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N , N-betaine, 1- [1- (3-nitronaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (4-nitronaphthyl)] methylidene -4,4-Dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (5-nitronaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine 1- [1- (6-Nitronaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (7-nitronaphthyl)] methylidene-4,4 -Dimethyl-3 -Oxopyrazolidine N, N-betaine, 1- [1- (8-nitronaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine and the like can be mentioned.

本発明の一般式(2)で表されるN,N−ベタイン誘導体として、4,4−ジメチル−3−オキソピラゾリン骨格を有し、Rが置換基を有しても良い2−ナフチル基であるものとしては、具体的には例えば、1−(2−ナフチルメチリデン)−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−メチルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(3−メチルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−メチルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(5−メチルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−メチルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(7−メチルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−メチルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−エチルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(3−エチルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−エチルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(5−エチルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−エチルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(7−エチルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−エチルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−n−プロピルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(3−n−プロピルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−n−プロピルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(5−n−プロピルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−n−プロピルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(7−n−プロピルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−n−プロピルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−iso−プロピルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(3−iso−プロピルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−iso−プロピルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(5−iso−プロピルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−iso−プロピルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(7−iso−プロピルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−iso−プロピルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−n−ブチルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(3−n−ブチルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−n−ブチルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(5−n−ブチルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−n−ブチルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(7−n−ブチルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−n−ブチルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−iso−ブチルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(3−iso−ブチルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−iso−ブチルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(5−iso−ブチルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−iso−ブチルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(7−iso−ブチルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−iso−ブチルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−tert−ブチルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(3−tert−ブチルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−tert−ブチルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(5−tert−ブチルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−tert−ブチルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(7−tert−ブチルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−tert−ブチルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−n−ペンチルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−n−ペンチルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−n−ペンチルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−n−ペンチルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−n−ヘキシルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−n−ヘキシルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−n−ヘキシルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−n−ヘキシルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−n−ヘプチルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−n−ヘプチルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−n−ヘプチルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−n−ヘプチルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−n−オクチルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−n−オクチルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−n−オクチルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−n−オクチルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−n−ノニルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−n−ノニルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−n−ノニルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−n−ノニルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−n−デシルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−n−デシルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−n−デシルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−n−デシルナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−メトキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(3−メトキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−メトキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(5−メトキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−メトキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(7−メトキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−メトキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−エトキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(3−エトキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−エトキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(5−エトキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−エトキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(7−エトキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−エトキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−n−プロポキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(3−n−プロポキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−n−プロポキシナフチル)]メチリデン−4,4−ジメチル−3−
オキソピラゾリジン N,N−ベタイン、1−[2−(5−n−プロポキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−n−プロポキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(7−n−プロポキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−n−プロポキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−iso−プロポキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(3−iso−プロポキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−iso−プロポキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(5−iso−プロポキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−iso−プロポキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(7−iso−プロポキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−iso−プロポキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−n−ブトキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(3−n−ブトキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−n−ブトキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(5−n−ブトキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−n−ブトキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(7−n−ブトキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−n−ブトキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−iso−ブトキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(3−iso−ブトキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−iso−ブトキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(5−iso−ブトキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−iso−ブトキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(7−iso−ブトキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−iso−ブトキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−tert−ブトキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(3−tert−ブトキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−tert−ブトキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(5−tert−ブトキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−tert−ブトキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(7−tert−ブトキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−tert−ブトキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−n−ペントキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−n−ペントキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−n−ペントキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−n−ペントキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−n−ヘキシルオキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−n−ヘキシルオキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−n−ヘキシルオキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−n−ヘキシルオキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−n−ヘプチルオキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−n−ヘプチルオキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−n−ヘプチルオキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−n−ヘプチルオキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−n−オクチルオキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−n−オクチルオキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−n−オクチルオキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−n−オクチルオキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−n−ノニルオキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−n−ノニルオキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−n−ノニルオキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−n−ノニルオキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−n−デシルオキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−n−デシルオキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−n−デシルオキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−n−デシルオキシナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−フルオロナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(3−フルオロナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−フルオロナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(5−フルオロナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−フルオロナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(7−フルオロナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−フルオロナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−クロロナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(3−クロロナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−クロロナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(5−クロロナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−クロロナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(7−クロロナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−クロロナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−ブロモナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(3−ブロモナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−ブロモナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(5−ブロモナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−ブロモナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(7−ブロモナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−ブロモナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−シアノナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(3−シアノナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−シアノナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(5−シアノナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−シアノナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(7−シアノナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−シアノナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−ニトロナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(3−ニトロナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−ニトロナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(5−ニトロナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−ニトロナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(7−ニトロナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−ニトロナフチル)]メチリデン−4,4−ジメチル−3−オキソピラゾリ
ジン N,N−ベタイン等を挙げることができる。
As the N, N-betaine derivative represented by the general formula (2) of the present invention, a 2-naphthyl group having a 4,4-dimethyl-3-oxopyrazolin skeleton and R 3 may have a substituent. Specific examples include 1- (2-naphthylmethylidene) -4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (1-methylnaphthyl) ] Methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (3-methylnaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N -Betaine, 1- [2- (4-methylnaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (5-methylnaphthyl)] methylidene-4 , 4-Dimethyl-3-Oki Pyrazolidine N, N-betaine, 1- [2- (6-methylnaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (7-methylnaphthyl) ] Methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (8-methylnaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N -Betaine, 1- [2- (1-ethylnaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (3-ethylnaphthyl)] methylidene-4 , 4-Dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (4-ethylnaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1 − [ -(5-Ethylnaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (6-ethylnaphthyl)] methylidene-4,4-dimethyl-3- Oxopyrazolidine N, N-betaine, 1- [2- (7-ethylnaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (8- Ethyl naphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (1-n-propylnaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazine Zolidine N, N-betaine, 1- [2- (3-n-propylnaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (4- n-propyl naphthy L)] Methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (5-n-propylnaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazo Lysine N, N-betaine, 1- [2- (6-n-propylnaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (7-n -Propylnaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (8-n-propylnaphthyl)] methylidene-4,4-dimethyl-3-oxo Pyrazolidine N, N-betaine, 1- [2- (1-iso-propylnaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (3 -Iso-propyl Butyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (4-iso-propylnaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazo Lysine N, N-betaine, 1- [2- (5-iso-propylnaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (6-iso -Propylnaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (7-iso-propylnaphthyl)] methylidene-4,4-dimethyl-3-oxo Pyrazolidine N, N-betaine, 1- [2- (8-iso-propylnaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- 1-n-butylnaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (3-n-butylnaphthyl)] methylidene-4,4-dimethyl- 3-oxopyrazolidine N, N-betaine, 1- [2- (4-n-butylnaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2 -(5-n-butylnaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (6-n-butylnaphthyl)] methylidene-4,4- Dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (7-n-butylnaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (8-n-butyl Naphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (1-iso-butylnaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazo Lysine N, N-betaine, 1- [2- (3-iso-butylnaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (4-iso -Butylnaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (5-iso-butylnaphthyl)] methylidene-4,4-dimethyl-3-oxo Pyrazolidine N, N-betaine, 1- [2- (6-iso-butylnaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (7 -Is -Butylnaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (8-iso-butylnaphthyl)] methylidene-4,4-dimethyl-3-oxo Pyrazolidine N, N-betaine, 1- [2- (1-tert-butylnaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (3 -Tert-butylnaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (4-tert-butylnaphthyl)] methylidene-4,4-dimethyl-3 -Oxopyrazolidine N, N-betaine, 1- [2- (5-tert-butylnaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1 [2- (6-tert-Butylnaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (7-tert-butylnaphthyl)] methylidene-4, 4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (8-tert-butylnaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (1-n-pentylnaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (4-n-pentylnaphthyl)] methylidene- 4,4-Dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (6-n-pentylnaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N- Solid In, 1- [2- (8-n-pentylnaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (1-n-hexylnaphthyl)] Methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (4-n-hexylnaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (6-n-hexylnaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (8-n-hexylnaphthyl) )] Methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (1-n-heptylnaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-Betai , 1- [2- (4-n-heptylnaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (6-n-heptylnaphthyl)] methylidene -4,4-Dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (8-n-heptylnaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N -Betaine, 1- [2- (1-n-octylnaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (4-n-octylnaphthyl) ] Methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (6-n-octylnaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N , N-betaine 1- [2- (8-n-octylnaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (1-n-nonylnaphthyl)] methylidene- 4,4-Dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (4-n-nonylnaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N- Betaine, 1- [2- (6-n-nonylnaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (8-n-nonylnaphthyl)] Methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (1-n-decylnaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- ( 4-n-decylnaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (6-n-decylnaphthyl)] methylidene-4,4-dimethyl- 3-oxopyrazolidine N, N-betaine, 1- [2- (8-n-decylnaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2 -(1-Methoxynaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (3-methoxynaphthyl)] methylidene-4,4-dimethyl-3- Oxopyrazolidine N, N-betaine, 1- [2- (4-methoxynaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (5- Methoxynaphthyl ] Methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (6-methoxynaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N -Betaine, 1- [2- (7-methoxynaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (8-methoxynaphthyl)] methylidene-4 , 4-Dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (1-ethoxynaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1 -[2- (3-Ethoxynaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (4-ethoxynaphthyl)] methylidene-4,4-di Tyl-3-oxopyrazolidine N, N-betaine, 1- [2- (5-ethoxynaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2 -(6-Ethoxynaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (7-ethoxynaphthyl)] methylidene-4,4-dimethyl-3- Oxopyrazolidine N, N-betaine, 1- [2- (8-ethoxynaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (1- n-propoxynaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (3-n-propoxynaphthyl)] methylidene-4,4-dimethyl-3- Oki Sopyrazolidine N, N-betaine, 1- [2- (4-n-propoxynaphthyl)] methylidene-4,4-dimethyl-3-
Oxopyrazolidine N, N-betaine, 1- [2- (5-n-propoxynaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- ( 6-n-propoxynaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (7-n-propoxynaphthyl)] methylidene-4,4-dimethyl- 3-oxopyrazolidine N, N-betaine, 1- [2- (8-n-propoxynaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2 -(1-iso-propoxynaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (3-iso-propoxynaphthyl)] methylidene-4, -Dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (4-iso-propoxynaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1 -[2- (5-iso-propoxynaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (6-iso-propoxynaphthyl)] methylidene-4 , 4-Dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (7-iso-propoxynaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine 1- [2- (8-iso-propoxynaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (1-n-butoxy) Butyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (3-n-butoxynaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazo Lysine N, N-betaine, 1- [2- (4-n-butoxynaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (5-n -Butoxynaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (6-n-butoxynaphthyl)] methylidene-4,4-dimethyl-3-oxo Pyrazolidine N, N-betaine, 1- [2- (7-n-butoxynaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (8 -N-Butoxynaphth Til)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (1-iso-butoxynaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazo Lysine N, N-betaine, 1- [2- (3-iso-butoxynaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (4-iso -Butoxynaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (5-iso-butoxynaphthyl)] methylidene-4,4-dimethyl-3-oxo Pyrazolidine N, N-betaine, 1- [2- (6-iso-butoxynaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (7 iso-butoxynaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (8-iso-butoxynaphthyl)] methylidene-4,4-dimethyl-3- Oxopyrazolidine N, N-betaine, 1- [2- (1-tert-butoxynaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- ( 3-tert-butoxynaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (4-tert-butoxynaphthyl)] methylidene-4,4-dimethyl- 3-oxopyrazolidine N, N-betaine, 1- [2- (5-tert-butoxynaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N N-betaine, 1- [2- (6-tert-butoxynaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (7-tert-butoxynaphthyl) )] Methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (8-tert-butoxynaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (1-n-pentoxynaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (4-n -Pentoxynaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (6-n-pentoxynaphthyl)] methylidene-4,4-dimethyl-3 − Xopyrazolidine N, N-betaine, 1- [2- (8-n-pentoxynaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (1- n-hexyloxynaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (4-n-hexyloxynaphthyl)] methylidene-4,4-dimethyl- 3-oxopyrazolidine N, N-betaine, 1- [2- (6-n-hexyloxynaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [ 2- (8-n-hexyloxynaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (1-n-heptyloxynaphthyl)] methyl Den-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (4-n-heptyloxynaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N , N-betaine, 1- [2- (6-n-heptyloxynaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (8-n- Heptyloxynaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (1-n-octyloxynaphthyl)] methylidene-4,4-dimethyl-3- Oxopyrazolidine N, N-betaine, 1- [2- (4-n-octyloxynaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (6-n -Octyloxynaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (8-n-octyloxynaphthyl)] methylidene-4,4-dimethyl-3 -Oxopyrazolidine N, N-betaine, 1- [2- (1-n-nonyloxynaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2 -(4-n-nonyloxynaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (6-n-nonyloxynaphthyl)] methylidene-4, 4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (8-n-nonyloxynaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-beta In, 1- [2- (1-n-decyloxynaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (4-n-decyloxynaphthyl) )] Methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (6-n-decyloxynaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazo Lysine N, N-betaine, 1- [2- (8-n-decyloxynaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (1- Fluoronaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (3-fluoronaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, -Betaine, 1- [2- (4-fluoronaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (5-fluoronaphthyl)] methylidene-4 , 4-Dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (6-fluoronaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1 -[2- (7-Fluoronaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (8-fluoronaphthyl)] methylidene-4,4-dimethyl -3-oxopyrazolidine N, N-betaine, 1- [2- (1-chloronaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (3- Chloronaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (4-chloronaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (5-chloronaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (6-chloronaphthyl)] Methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (7-chloronaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N- Betaine, 1- [2- (8-chloronaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (1-bromonaphthyl)] methylidene-4, 4- Methyl-3-oxopyrazolidine N, N-betaine, 1- [2- (3-bromonaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2 -(4-Bromonaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (5-bromonaphthyl)] methylidene-4,4-dimethyl-3- Oxopyrazolidine N, N-betaine, 1- [2- (6-bromonaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (7- Bromonaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (8-bromonaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N Betaine, 1- [2- (1-cyanonaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (3-cyanonaphthyl)] methylidene-4, 4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (4-cyanonaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (5-Cyanonaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (6-cyanonaphthyl)] methylidene-4,4-dimethyl- 3-oxopyrazolidine N, N-betaine, 1- [2- (7-cyanonaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- ( 8-cyanonaphth L)] Methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (1-nitronaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N , N-betaine, 1- [2- (3-nitronaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (4-nitronaphthyl)] methylidene -4,4-Dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (5-nitronaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine , 1- [2- (6-Nitronaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (7-nitronaphthyl)] methylidene-4,4 -Dimethyl-3 -Oxopyrazolidine N, N-betaine, 1- [2- (8-nitronaphthyl)] methylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine and the like can be mentioned.

本発明の一般式(2)で表されるN,N−ベタイン誘導体として、4,4−ジメチル−3−オキソピラゾリン骨格を有し、Rが置換基を有しても良いアリールエチレニル基であるものとしては、具体的には例えば、1−(3−フェニルプロピリデン−2−エン)−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(2−メチルフェニル)プロピリデン−2−エン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(3−メチルフェニル)プロピリデン−2−エン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(4−メチルフェニル)プロピリデン−2−エン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(2−エチルフェニル)プロピリデン−2−エン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(3−エチルフェニル)プロピリデン−2−エン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(4−エチルフェニル)プロピリデン−2−エン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(2−n−プロピルフェニル)プロピリデン−2−エン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(3−n−プロピルフェニル)プロピリデン−2−エン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(4−n−プロピルフェニル)プロピリデン−2−エン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(2−iso−プロピルフェニル)プロピリデン−2−エン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(3−iso−プロピルフェニル)プロピリデン−2−エン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(4−iso−プロピルフェニル)プロピリデン−2−エン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(2−n−ブチルフェニル)プロピリデン−2−エン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(3−n−ブチルフェニル)プロピリデン−2−エン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(4−n−ブチルフェニル)プロピリデン−2−エン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(2−sec−ブチルフェニル)プロピリデン−2−エン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(3−sec−ブチルフェニル)プロピリデン−2−エン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(4−sec−ブチルフェニル)プロピリデン−2−エン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(2−tert−ブチルフェニル)プロピリデン−2−エン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(3−tert−ブチルフェニル)プロピリデン−2−エン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(4−tert−ブチルフェニル)プロピリデン−2−エン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(2−メトキシフェニル)プロピリデン−2−エン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(3−メトキシフェニル)プロピリデン−2−エン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(4−メトキシフェニル)プロピリデン−2−エン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(2−エトキシフェニル)プロピリデン−2−エン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(3−エトキシフェニル)プロピリデン−2−エン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(4−エトキシフェニル)プロピリデン−2−エン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(2−n−プロポキシフェニル)プロピリデン−2−エン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(3−n−プロポキシフェニル)プロピリデン−2−エン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(4−n−プロポキシフェニル)プロピリデン−2−エン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(2−iso−プロポキシフェニル)プロピリデン−2−エン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(3−iso−プロポキシフェニル)プロピリデン−2−エン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(4−iso−プロポキシフェニル)プロピリデン−2−エン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(2−n−ブトキシフェニル)プロピリデン−2−エン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(3−n−ブトキシフェニル)プロピリデン−2−エン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(4−n−ブトキシフェニル)プロピリデン−2−エン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(2−sec−ブトキシフェニル)プロピリデン−2−エン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(3−sec−ブトキシフェニル)プロピリデン−2−エン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(4−sec−ブトキシフェニル)プロピリデン−2−エン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(2−tert−ブトキシフェニル)プロピリデン−2−エン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(3−tert−ブトキシフェニル)プロピリデン−2−エン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(4−tert−ブトキシフェニル)プロピリデン−2−エン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(2−フルオロフェニル)プロピリデン−2−エン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(3−フルオロフェニル)プロピリデン−2−エン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(4−フルオロフェニル)プロピリデン−2−エン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(2−クロロフェニル)プロピリデン−2−エン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(3−クロロフェニル)プロピリデン−2−エン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(4−クロロフェニル)プロピリデン−2−エン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(2−ブロモフェニル)プロピリデン−2−エン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(3−ブロモフェニル)プロピリデン−2−エン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(4−ブロモフェニル)プロピリデン−2−エン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(2−シアノフェニル)プロピリデン−2−エン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(3−シアノフェニル)プロピリデン−2−エン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(4−シアノフェニル)プロピリデン−2−エン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(2−ニトロフェニル)プロピリデン−2−エン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(3−ニトロフェニル)プロピリデン−2−エン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(4−ニトロフェニル)プロピリデン−2−エン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン等を挙げることができる。 As an N, N-betaine derivative represented by the general formula (2) of the present invention, an arylethylenyl group having a 4,4-dimethyl-3-oxopyrazoline skeleton, and R 3 may have a substituent. As specific examples, for example, 1- (3-phenylpropylidene-2-ene) -4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [3- (2- Methylphenyl) propylidene-2-ene] -4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [3- (3-methylphenyl) propylidene-2-ene] -4,4- Dimethyl-3-oxopyrazolidine N, N-betaine, 1- [3- (4-methylphenyl) propylidene-2-ene] -4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [3- (2-D Ruphenyl) propylidene-2-ene] -4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [3- (3-ethylphenyl) propylidene-2-ene] -4,4-dimethyl -3-oxopyrazolidine N, N-betaine, 1- [3- (4-ethylphenyl) propylidene-2-ene] -4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1 -[3- (2-n-propylphenyl) propylidene-2-ene] -4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [3- (3-n-propylphenyl) Propylidene-2-ene] -4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [3- (4-n-propylphenyl) propylidene-2-ene] -4,4-dimethyl -3-Oki Pyrazolidine N, N-betaine, 1- [3- (2-iso-propylphenyl) propylidene-2-ene] -4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [3- (3-Iso-propylphenyl) propylidene-2-ene] -4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [3- (4-iso-propylphenyl) propylidene-2- Ene] -4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [3- (2-n-butylphenyl) propylidene-2-ene] -4,4-dimethyl-3-oxo Pyrazolidine N, N-betaine, 1- [3- (3-n-butylphenyl) propylidene-2-ene] -4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [ 3- ( -N-butylphenyl) propylidene-2-ene] -4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [3- (2-sec-butylphenyl) propylidene-2-ene] -4,4-Dimethyl-3-oxopyrazolidine N, N-betaine, 1- [3- (3-sec-butylphenyl) propylidene-2-ene] -4,4-dimethyl-3-oxopyrazo Lysine N, N-betaine, 1- [3- (4-sec-butylphenyl) propylidene-2-ene] -4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [3- (2-tert-Butylphenyl) propylidene-2-ene] -4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [3- (3-tert-butylphenyl) propylidene-2 Ene] -4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [3- (4-tert-butylphenyl) propylidene-2-ene] -4,4-dimethyl-3-oxo Pyrazolidine N, N-betaine, 1- [3- (2-methoxyphenyl) propylidene-2-ene] -4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [3- (3-methoxyphenyl) propylidene-2-ene] -4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [3- (4-methoxyphenyl) propylidin-2-ene] -4 , 4-Dimethyl-3-oxopyrazolidine N, N-betaine, 1- [3- (2-ethoxyphenyl) propylidene-2-ene] -4,4-dimethyl-3-oxopyrazolidine N, N -Betai 1- [3- (3-Ethoxyphenyl) propylidene-2-ene] -4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [3- (4-ethoxyphenyl) propylidene- 2-ene] -4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [3- (2-n-propoxyphenyl) propylidin-2-ene] -4,4-dimethyl-3 -Oxopyrazolidine N, N-betaine, 1- [3- (3-n-propoxyphenyl) propylidin-2-ene] -4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1 -[3- (4-n-propoxyphenyl) propylidene-2-ene] -4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [3- (2-iso-propoxyphenyl) Propyri N-2-ene] -4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [3- (3-iso-propoxyphenyl) propylidene-2-ene] -4,4-dimethyl -3-oxopyrazolidine N, N-betaine, 1- [3- (4-iso-propoxyphenyl) propylidene-2-ene] -4,4-dimethyl-3-oxopyrazolidine N, N-betaine 1- [3- (2-n-butoxyphenyl) propylidene-2-ene] -4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [3- (3-n-butoxy Phenyl) propylidene-2-ene] -4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [3- (4-n-butoxyphenyl) propylidene-2-ene] -4,4 -Dimethyl-3-o Xopyrazolidine N, N-betaine, 1- [3- (2-sec-butoxyphenyl) propylidene-2-ene] -4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [3- (3-sec-butoxyphenyl) propylidene-2-ene] -4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [3- (4-sec-butoxyphenyl) propylidene-2- Ene] -4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [3- (2-tert-butoxyphenyl) propylidene-2-ene] -4,4-dimethyl-3-oxo Pyrazolidine N, N-betaine, 1- [3- (3-tert-butoxyphenyl) propylidene-2-ene] -4,4-dimethyl-3-oxopyrazolidine N, N-beta 1- [3- (4-tert-butoxyphenyl) propylidene-2-ene] -4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [3- (2-fluorophenyl) ) Propylidene-2-ene] -4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [3- (3-fluorophenyl) propylidene-2-ene] -4,4-dimethyl- 3-oxopyrazolidine N, N-betaine, 1- [3- (4-fluorophenyl) propylidene-2-ene] -4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [3- (2-Chlorophenyl) propylidene-2-ene] -4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [3- (3-chlorophenyl) propylidene-2-ene]- 4 , 4-Dimethyl-3-oxopyrazolidine N, N-betaine, 1- [3- (4-chlorophenyl) propylidene-2-ene] -4,4-dimethyl-3-oxopyrazolidine N, N- Betaine, 1- [3- (2-bromophenyl) propylidene-2-ene] -4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [3- (3-bromophenyl) propylidene -2-ene] -4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [3- (4-bromophenyl) propylidene-2-ene] -4,4-dimethyl-3- Oxopyrazolidine N, N-betaine, 1- [3- (2-cyanophenyl) propylidene-2-ene] -4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [3 -(3-Cyanofe L) propylidene-2-ene] -4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [3- (4-cyanophenyl) propylidene-2-ene] -4,4-dimethyl -3-oxopyrazolidine N, N-betaine, 1- [3- (2-nitrophenyl) propylidene-2-ene] -4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1 -[3- (3-Nitrophenyl) propylidene-2-ene] -4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [3- (4-nitrophenyl) propylidene-2- Ene] -4,4-dimethyl-3-oxopyrazolidine N, N-betaine and the like.

本発明の一般式(2)で表されるN,N−ベタイン誘導体として、4,4−ジメチル−3−オキソピラゾリン骨格を有し、Rが置換基を有しても良いアリールアルキル基であるものとしては、具体的には例えば、1−(2−フェニルエチリデン)−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(3−フェニルプロピリデン)−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(4−フェニルブチリデン)−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(5−フェニルペンチリデン)−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(6−フェニルヘキシリデン)−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(2−メチルフェニル)エチリデン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(3−メチルフェニル)エチリデン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−メチルフェニル)エチリデン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(2−メチルフェニル)プロピリデン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(3−メチルフェニル)プロピリデン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(4−メチルフェニル)プロピリデン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[4−(2−メチルフェニル)ブチリデン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[4−(3−メチルフェニル)ブチリデン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[4−(4−メチルフェニル)ブチリデン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[5−(2−メチルフェニル)ペンチリデン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[5−(3−メチルフェニル)ペンチリデン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[5−(4−メチルフェニル)ペンチリデン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(2−エチルフェニル)エチリデン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(3−エチルフェニル)エチリデン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−エチルフェニル)エチリデン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(2−エチルフェニル)プロピリデン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(3−エチルフェニル)プロピリデン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(4−エチルフェニル)プロピリデン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[4−(2−エチルフェニル)ブチリデン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[4−(3−エチルフェニル)ブチリデン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[4−(4−エチルフェニル)ブチリデン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[5−(2−エチルフェニル)ペンチリデン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[5−(3−エチルフェニル)ペンチリデン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[5−(4−エチルフェニル)ペンチリデン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(2−メトキシフェニル)エチリデン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(3−メトキシフェニル)エチリデン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−メトキシフェニル)エチリデン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(2−メトキシフェニル)プロピリデン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(3−メトキシフェニル)プロピリデン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(4−メトキシフェニル)プロピリデン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[4−(2−メトキシフェニル)ブチリデン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[4−(3−メトキシフェニル)ブチリデン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[4−(4−メトキシフェニル)ブチリデン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[5−(2−メトキシフェニル)ペンチリデン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[5−(3−メトキシフェニル)ペンチリデン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[5−(4−メトキシフェニル)ペンチリデン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(2−エトキシフェニル)エチリデン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(3−エトキシフェニル)エチリデン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−エトキシフェニル)エチリデン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(2−エトキシフェニル)プロピリデン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(3−エトキシフェニル)プロピリデン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(4−エトキシフェニル)プロピリデン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[4−(2−エトキシフェニル)ブチリデン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[4−(3−エトキシフェニル)ブチリデン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[4−(4−エトキシフェニル)ブチリデン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[5−(2−エトキシフェニル)ペンチリデン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[5−(3−エトキシフェニル)ペンチリデン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[5−(4−エトキシフェニル)ペンチリデン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(2−フルオロフェニル)エチリデン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(3−フルオロフェニル)エチリデン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−フルオロフェニル)エチリデン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(2−フルオロフェニル)プロピリデン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(3−フルオロフェニル)プロピリデン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(4−フルオロフェニル)プロピリデン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[4−(2−フルオロフェニル)ブチリデン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[4−(3−フルオロフェニル)ブチリデン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[4−(4−フルオロフェニル)ブチリデン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[5−(2−フルオロフェニル)ペンチリデン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[5−(3−フルオロフェニル)ペンチリデン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[5−(4−フルオロフェニル)ペンチリデン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(2−クロロフェニル)エチリデン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(3−クロロフェニル)エチリデン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−クロロフェニル)エチリデン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(2−クロロフェニル)プロピリデン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(3−クロロフェニル)プロピリデン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(4−クロロフェニル)プロピリデン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[4−(2−クロロフェニル)ブチリデン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[4−(3−クロロフェニル)ブチリデン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[4−(4−クロロフェニル)ブチリデン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[5−(2−クロロフェニル)ペンチリデン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[5−(3−クロロフェニル)ペンチリデン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[5−(4−クロロフェニル)ペンチリデン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(2−ブロモフェニル)エチリデン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(3−ブロモフェニル)エチリデン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−ブロモフェニル)エチリデン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(2−ブロモフェニル)プロピリデン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(3−ブロモフェニル)プロピリデン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(4−ブロモフェニル)プロピリデン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[4−(2−ブロモフェニル)ブチリデン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[4−(3−ブロモフェニル)ブチリデン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[4−(4−ブロモフェニル)ブチリデン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[5−(2−ブロモフェニル)ペンチリデン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[5−(3−ブロモフェニル)ペンチリデン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[5−(4−ブロモフェニル)ペンチリデン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(2−シアノフェニル)エチリデン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(3−シアノフェニル)エチリデン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−シアノフェニル)エチリデン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(2−シアノフェニル)プロピリデン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(3−シアノフェニル)プロピリデン]−4,4−ジメチル−3−オキソピラゾリ
ジン N,N−ベタイン、1−[3−(4−シアノフェニル)プロピリデン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[4−(2−シアノフェニル)ブチリデン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[4−(3−シアノフェニル)ブチリデン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[4−(4−シアノフェニル)ブチリデン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[5−(2−シアノフェニル)ペンチリデン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[5−(3−シアノフェニル)ペンチリデン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[5−(4−シアノフェニル)ペンチリデン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(2−ニトロフェニル)エチリデン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(3−ニトロフェニル)エチリデン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−ニトロフェニル)エチリデン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(2−ニトロフェニル)プロピリデン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(3−ニトロフェニル)プロピリデン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(4−ニトロフェニル)プロピリデン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[4−(2−ニトロフェニル)ブチリデン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[4−(3−ニトロフェニル)ブチリデン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[4−(4−ニトロフェニル)ブチリデン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[5−(2−ニトロフェニル)ペンチリデン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[5−(3−ニトロフェニル)ペンチリデン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[5−(4−ニトロフェニル)ペンチリデン]−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン等を挙げることができる。
The N, N-betaine derivative represented by the general formula (2) of the present invention is an arylalkyl group that has a 4,4-dimethyl-3-oxopyrazolin skeleton and R 3 may have a substituent. Specifically, for example, 1- (2-phenylethylidene) -4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- (3-phenylpropylidene) -4,4- Dimethyl-3-oxopyrazolidine N, N-betaine, 1- (4-phenylbutylidene) -4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- (5-phenylpentylidene ) -4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- (6-phenylhexylidene) -4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1 − [2- (2 Methylphenyl) ethylidene] -4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (3-methylphenyl) ethylidene] -4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (4-methylphenyl) ethylidene] -4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [3- (2-methylphenyl) propylidene ] -4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [3- (3-methylphenyl) propylidene] -4,4-dimethyl-3-oxopyrazolidine N, N- Betaine, 1- [3- (4-methylphenyl) propylidene] -4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [4- (2-methylphenyl) butylidene]- , 4-Dimethyl-3-oxopyrazolidine N, N-betaine, 1- [4- (3-methylphenyl) butylidene] -4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1 -[4- (4-Methylphenyl) butylidene] -4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [5- (2-methylphenyl) pentylidene] -4,4-dimethyl -3-oxopyrazolidine N, N-betaine, 1- [5- (3-methylphenyl) pentylidene] -4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [5- (4-Methylphenyl) pentylidene] -4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (2-ethylphenyl) ethylidene] -4,4-dimethyl-3-oxopyrazo Lysine N, N-betaine, 1- [2- (3-ethylphenyl) ethylidene] -4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (4-ethylphenyl) Ethylidene] -4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [3- (2-ethylphenyl) propylidene] -4,4-dimethyl-3-oxopyrazolidine N, N -Betaine, 1- [3- (3-ethylphenyl) propylidene] -4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [3- (4-ethylphenyl) propylidene] -4 , 4-Dimethyl-3-oxopyrazolidine N, N-betaine, 1- [4- (2-ethylphenyl) butylidene] -4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1 -[4 -(3-Ethylphenyl) butylidene] -4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [4- (4-ethylphenyl) butylidene] -4,4-dimethyl-3- Oxopyrazolidine N, N-betaine, 1- [5- (2-ethylphenyl) pentylidene] -4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [5- (3- Ethylphenyl) pentylidene] -4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [5- (4-ethylphenyl) pentylidene] -4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (2-methoxyphenyl) ethylidene] -4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (3-methoxyphenyl) ethyl Den] -4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (4-methoxyphenyl) ethylidene] -4,4-dimethyl-3-oxopyrazolidine N, N -Betaine, 1- [3- (2-methoxyphenyl) propylidene] -4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [3- (3-methoxyphenyl) propylidene] -4 , 4-Dimethyl-3-oxopyrazolidine N, N-betaine, 1- [3- (4-methoxyphenyl) propylidene] -4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1 -[4- (2-methoxyphenyl) butylidene] -4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [4- (3-methoxyphenyl) butylidene] -4,4-di Tyl-3-oxopyrazolidine N, N-betaine, 1- [4- (4-methoxyphenyl) butylidene] -4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [5 -(2-Methoxyphenyl) pentylidene] -4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [5- (3-methoxyphenyl) pentylidene] -4,4-dimethyl-3- Oxopyrazolidine N, N-betaine, 1- [5- (4-methoxyphenyl) pentylidene] -4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (2- Ethoxyphenyl) ethylidene] -4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (3-ethoxyphenyl) ethylidene] -4,4-dimethyl-3-oxopyra Zolidine N, N-betaine, 1- [2- (4-ethoxyphenyl) ethylidene] -4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [3- (2-ethoxyphenyl) Propylidene] -4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [3- (3-ethoxyphenyl) propylidene] -4,4-dimethyl-3-oxopyrazolidine N, N -Betaine, 1- [3- (4-ethoxyphenyl) propylidene] -4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [4- (2-ethoxyphenyl) butylidene] -4 , 4-Dimethyl-3-oxopyrazolidine N, N-betaine, 1- [4- (3-ethoxyphenyl) butylidene] -4,4-dimethyl-3-oxopyrazolidine N, N-beta In, 1- [4- (4-ethoxyphenyl) butylidene] -4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [5- (2-ethoxyphenyl) pentylidene] -4, 4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [5- (3-ethoxyphenyl) pentylidene] -4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [5- (4-Ethoxyphenyl) pentylidene] -4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (2-fluorophenyl) ethylidene] -4,4-dimethyl- 3-oxopyrazolidine N, N-betaine, 1- [2- (3-fluorophenyl) ethylidene] -4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- ( 4 Fluorophenyl) ethylidene] -4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [3- (2-fluorophenyl) propylidene] -4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [3- (3-fluorophenyl) propylidene] -4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [3- (4-fluorophenyl) propylidene ] -4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [4- (2-fluorophenyl) butylidene] -4,4-dimethyl-3-oxopyrazolidine N, N- Betaine, 1- [4- (3-fluorophenyl) butylidene] -4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [4- (4-fluorophenyl) Tylidene] -4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [5- (2-fluorophenyl) pentylidene] -4,4-dimethyl-3-oxopyrazolidine N, N -Betaine, 1- [5- (3-fluorophenyl) pentylidene] -4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [5- (4-fluorophenyl) pentylidene] -4 , 4-Dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (2-chlorophenyl) ethylidene] -4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (3-Chlorophenyl) ethylidene] -4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (4-chlorophenyl) ethylidene] -4,4-dimethyl Ru-3-oxopyrazolidine N, N-betaine, 1- [3- (2-chlorophenyl) propylidene] -4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [3- (3-Chlorophenyl) propylidene] -4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [3- (4-chlorophenyl) propylidene] -4,4-dimethyl-3-oxopyrazo Lysine N, N-betaine, 1- [4- (2-chlorophenyl) butylidene] -4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [4- (3-chlorophenyl) butylidene] -4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [4- (4-chlorophenyl) butylidene] -4,4-dimethyl-3-oxopyrazolidine N, N -Betaine, 1- [5- (2-chlorophenyl) pentylidene] -4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [5- (3-chlorophenyl) pentylidene] -4,4 -Dimethyl-3-oxopyrazolidine N, N-betaine, 1- [5- (4-chlorophenyl) pentylidene] -4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2 -(2-Bromophenyl) ethylidene] -4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (3-bromophenyl) ethylidene] -4,4-dimethyl-3- Oxopyrazolidine N, N-betaine, 1- [2- (4-bromophenyl) ethylidene] -4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [3- (2- Bro Phenyl) propylidene] -4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [3- (3-bromophenyl) propylidene] -4,4-dimethyl-3-oxopyrazolidine N , N-betaine, 1- [3- (4-bromophenyl) propylidene] -4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [4- (2-bromophenyl) butylidene] -4,4-Dimethyl-3-oxopyrazolidine N, N-betaine, 1- [4- (3-bromophenyl) butylidene] -4,4-dimethyl-3-oxopyrazolidine N, N-betaine 1- [4- (4-bromophenyl) butylidene] -4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [5- (2-bromophenyl) pentylidene] -4, -Dimethyl-3-oxopyrazolidine N, N-betaine, 1- [5- (3-bromophenyl) pentylidene] -4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [ 5- (4-Bromophenyl) pentylidene] -4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (2-cyanophenyl) ethylidene] -4,4-dimethyl-3 -Oxopyrazolidine N, N-betaine, 1- [2- (3-cyanophenyl) ethylidene] -4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (4 -Cyanophenyl) ethylidene] -4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [3- (2-cyanophenyl) propylidene] -4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [3- (3-cyanophenyl) propylidene] -4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [3- (4-cyanophenyl) Propylidene] -4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [4- (2-cyanophenyl) butylidene] -4,4-dimethyl-3-oxopyrazolidine N, N -Betaine, 1- [4- (3-cyanophenyl) butylidene] -4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [4- (4-cyanophenyl) butylidene] -4 , 4-Dimethyl-3-oxopyrazolidine N, N-betaine, 1- [5- (2-cyanophenyl) pentylidene] -4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1 -[5- ( 3-cyanophenyl) pentylidene] -4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [5- (4-cyanophenyl) pentylidene] -4,4-dimethyl-3-oxopyra Zolidine N, N-betaine, 1- [2- (2-nitrophenyl) ethylidene] -4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (3-nitrophenyl) ) Ethylidene] -4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (4-nitrophenyl) ethylidene] -4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [3- (2-nitrophenyl) propylidene] -4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [3- (3-nitrophenyl) propylidene -4,4-Dimethyl-3-oxopyrazolidine N, N-betaine, 1- [3- (4-nitrophenyl) propylidene] -4,4-dimethyl-3-oxopyrazolidine N, N-betaine 1- [4- (2-nitrophenyl) butylidene] -4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [4- (3-nitrophenyl) butylidene] -4,4 -Dimethyl-3-oxopyrazolidine N, N-betaine, 1- [4- (4-nitrophenyl) butylidene] -4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [ 5- (2-Nitrophenyl) pentylidene] -4,4-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [5- (3-nitrophenyl) pentylidene] -4,4-dimethyl-3 -Oxo Razorijin N, N- betaine, 1- [5- (4-nitrophenyl) pentylidene] -4,4-dimethyl-3-oxo-pyrazolidine N, can be mentioned N- betaine.

本発明の一般式(2)で表されるN,N−ベタイン誘導体として、5,5−ジメチル−3−オキソピラゾリン骨格を有し、Rがメチル基、エチル基、炭素数3〜10の直鎖、分岐若しくは環式のアルキル基であるものとしては、具体的には例えば、1−(エチリデン)−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(n−プロピリデン)−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(n−ブチリデン)−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(2−メチルプロピリデン)−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(n−ペンチレリデン)−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(2,2−ジメチルプロピリデン)−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(n−ヘキシリデン)−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(n−ヘプチリデン)−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(シクロヘキシルメチリデン)−5,5−ジメチル−3−オキソピラゾリン N,N−ベタイン、1−(n−オクチリデン)−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(n−ノナニリデン)−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(n−デシリデン)−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(n−ウンデシリデン)−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン等を挙げることができる。 The N, N-betaine derivative represented by the general formula (2) of the present invention has a 5,5-dimethyl-3-oxopyrazoline skeleton, and R 3 is a methyl group, an ethyl group, a straight chain having 3 to 10 carbon atoms. Specific examples of the chain, branched or cyclic alkyl group include 1- (ethylidene) -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- (n- Propylidene) -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- (n-butylidene) -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- ( 2-Methylpropylidene) -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- (n-pentylidene) -5,5-dimethyl-3-oxopyrazolidine N, N-betaine , 1- (2,2-dimension Rupropylidene) -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- (n-hexylidene) -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- ( n-heptylidene) -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- (cyclohexylmethylidene) -5,5-dimethyl-3-oxopyrazolin N, N-betaine, 1- (n -Octylidene) -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- (n-nonanilidene) -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- (N-decylidene) -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- (n-undecylidene) -5,5-dimethyl-3-oxopyrazolidine N, N- Examples include betaine.

本発明の一般式(2)で表されるN,N−ベタイン誘導体として、5,5−ジメチル−3−オキソピラゾリン骨格を有し、Rが置換基を有しても良いフェニル基であるものとしては、具体的には例えば、1−ベンジリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(2−メチルフェニル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(3−メチルフェニル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(4−メチルフェニル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(2−エチルフェニル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(3−エチルフェニル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(4−エチルフェニル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(2−n−プロピルフェニル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(3−n−プロピルフェニル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(4−n−プロピルフェニル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(2−iso−プロピルフェニル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(3−iso−プロピルフェニル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(4−iso−プロピルフェニル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(2−n−ブチルフェニル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(3−n−ブチルフェニル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(4−n−ブチルフェニル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(2−iso−ブチルフェニル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(3−iso−ブチルフェニル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(4−iso−ブチルフェニル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(2−tert−ブチルフェニル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(3−tert−ブチルフェニル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(4−tert−ブチルフェニル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(4−n−ペンチルフェニル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(4−n−ヘキシルフェニル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(4−n−ヘプチルフェニル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(4−n−オクチルフェニル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(4−n−ノニルフェニル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(4−n−デシルフェニル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(2−メトキシフェニル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(3−メトキシフェニル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(4−メトキシフェニル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(2−エトキシフェニル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(3−エトキシフェニル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(4−エトキシフェニル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(2−n−プロポキシフェニル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(3−n−プロポキシフェニル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(4−n−プロポキシフェニル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(2−iso−プロポキシフェニル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(3−iso−プロポキシフェニル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(4−iso−プロポキシフェニル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(2−n−ブトキシフェニル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(3−n−ブトキシフェニル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(4−n−ブトキシフェニル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(2−iso−ブトキシフェニル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(3−iso−ブトキシフェニル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(4−iso−ブトキシフェニル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(2−tert−ブトキシフェニル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(3−tert−ブトキシフェニル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(4−tert−ブトキシフェニル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(4−n−ペントキシフェニル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(4−n−ヘキシルオキシフェニル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(4−n−ヘプチルオキシフェニル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(4−n−オクチルオキシフェニル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(4−n−ノニルオキシフェニル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(4−n−デシルオキシフェニル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(2−フルオロフェニル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(3−フルオロフェニル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(4−フルオロフェニル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(2−クロロフェニル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(3−クロロフェニル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(4−クロロフェニル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(2−ブロモフェニル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(3−ブロモフェニル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(4−ブロモフェニル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(2−シアノフェニル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(3−シアノフェニル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(4−シアノフェニル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(2−ニトロフェニル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(3−ニトロフェニル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(4−ニトロフェニル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン等を挙げることができる。 The N, N-betaine derivative represented by the general formula (2) of the present invention has a 5,5-dimethyl-3-oxopyrazoline skeleton, and R 3 is a phenyl group which may have a substituent. Specifically, for example, 1-benzylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- (2-methylphenyl) methylidene-5,5-dimethyl-3-oxo Pyrazolidine N, N-betaine, 1- (3-methylphenyl) methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- (4-methylphenyl) methylidene-5,5 -Dimethyl-3-oxopyrazolidine N, N-betaine, 1- (2-ethylphenyl) methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- (3-ethylphen Nyl) methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- (4-ethylphenyl) methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- (2-n-propylphenyl) methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- (3-n-propylphenyl) methylidene-5,5-dimethyl-3- Oxopyrazolidine N, N-betaine, 1- (4-n-propylphenyl) methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- (2-iso-propylphenyl) Methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- (3-iso-propylphenyl) methylidene-5,5-dimethyl-3-oxo Lazolidine N, N-betaine, 1- (4-iso-propylphenyl) methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- (2-n-butylphenyl) methylidene-5 , 5-Dimethyl-3-oxopyrazolidine N, N-betaine, 1- (3-n-butylphenyl) methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- ( 4-n-butylphenyl) methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- (2-iso-butylphenyl) methylidene-5,5-dimethyl-3-oxopyrazo Lysine N, N-betaine, 1- (3-iso-butylphenyl) methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- (4-iso- Tylphenyl) methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- (2-tert-butylphenyl) methylidene-5,5-dimethyl-3-oxopyrazolidine N, N- Betaine, 1- (3-tert-butylphenyl) methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- (4-tert-butylphenyl) methylidene-5,5-dimethyl- 3-oxopyrazolidine N, N-betaine, 1- (4-n-pentylphenyl) methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- (4-n-hexyl) Phenyl) methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- (4-n-heptylphenyl) methylidene-5,5-dimethyl Tyl-3-oxopyrazolidine N, N-betaine, 1- (4-n-octylphenyl) methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- (4-n -Nonylphenyl) methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- (4-n-decylphenyl) methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- (2-methoxyphenyl) methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- (3-methoxyphenyl) methylidene-5,5-dimethyl-3- Oxopyrazolidine N, N-betaine, 1- (4-methoxyphenyl) methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- (2-ethoxyphenyl) Enyl) methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- (3-ethoxyphenyl) methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- (4-Ethoxyphenyl) methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- (2-n-propoxyphenyl) methylidene-5,5-dimethyl-3-oxopyra Zolidine N, N-betaine, 1- (3-n-propoxyphenyl) methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- (4-n-propoxyphenyl) methylidene- 5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- (2-iso-propoxyphenyl) methylidene-5,5-dimethyl-3-oxy Pyrazolidine N, N-betaine, 1- (3-iso-propoxyphenyl) methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- (4-iso-propoxyphenyl) methylidene-5 , 5-Dimethyl-3-oxopyrazolidine N, N-betaine, 1- (2-n-butoxyphenyl) methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- ( 3-n-butoxyphenyl) methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- (4-n-butoxyphenyl) methylidene-5,5-dimethyl-3-oxopyrazo Lysine N, N-betaine, 1- (2-iso-butoxyphenyl) methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1 (3-iso-butoxyphenyl) methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- (4-iso-butoxyphenyl) methylidene-5,5-dimethyl-3-oxopyra Zolidine N, N-betaine, 1- (2-tert-butoxyphenyl) methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- (3-tert-butoxyphenyl) methylidene- 5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- (4-tert-butoxyphenyl) methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- (4-n-pentoxyphenyl) methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- (4-n-hexylo) Ciphenyl) methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- (4-n-heptyloxyphenyl) methylidene-5,5-dimethyl-3-oxopyrazolidine N, N -Betaine, 1- (4-n-octyloxyphenyl) methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- (4-n-nonyloxyphenyl) methylidene-5,5 -Dimethyl-3-oxopyrazolidine N, N-betaine, 1- (4-n-decyloxyphenyl) methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- (2 -Fluorophenyl) methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- (3-fluorophenyl) methylidene-5,5-dimethyl Ru-3-oxopyrazolidine N, N-betaine, 1- (4-fluorophenyl) methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- (2-chlorophenyl) methylidene -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- (3-chlorophenyl) methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- (4 -Chlorophenyl) methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- (2-bromophenyl) methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine 1- (3-bromophenyl) methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- (4-bromophenyl) methylidene-5 , 5-Dimethyl-3-oxopyrazolidine N, N-betaine, 1- (2-cyanophenyl) methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- (3- Cyanophenyl) methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- (4-cyanophenyl) methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine 1- (2-nitrophenyl) methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- (3-nitrophenyl) methylidene-5,5-dimethyl-3-oxopyrazo Examples include lysine N, N-betaine and 1- (4-nitrophenyl) methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine.

本発明の一般式(2)で表されるN,N−ベタイン誘導体として、5,5−ジメチル−3−オキソピラゾリン骨格を有し、Rが置換基を有しても良い1−ナフチル基であるものとしては、具体的には例えば、1−(1−ナフチルメチリデン)−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−メチルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(3−メチルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−メチルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(5−メチルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−メチルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(7−メチルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−メチルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−エチルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(3−エチルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−エチルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(5−エチルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−エチルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(7−エチルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−エチルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−n−プロピルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(3−n−プロピルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−n−プロピルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(5−n−プロピルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−n−プロピルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(7−n−プロピルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−n−プロピルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−iso−プロピルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(3−iso−プロピルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−iso−プロピルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(5−iso−プロピルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−iso−プロピルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(7−iso−プロピルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−iso−プロピルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−n−ブチルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(3−n−ブチルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−n−ブチルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(5−n−ブチルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−n−ブチルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(7−n−ブチルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−n−ブチルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−iso−ブチルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(3−iso−ブチルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−iso−ブチルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(5−iso−ブチルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−iso−ブチルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(7−iso−ブチルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−iso−ブチルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−tert−ブチルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(3−tert−ブチルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−tert−ブチルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(5−tert−ブチルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−tert−ブチルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(7−tert−ブチルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−tert−ブチルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−n−ペンチルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−n−ペンチルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−n−ペンチルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−n−ペンチルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−n−ヘキシルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−n−ヘキシルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−n−ヘキシルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−n−ヘキシルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−n−ヘプチルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−n−ヘプチルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−n−ヘプチルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−n−ヘプチルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−n−オクチルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−n−オクチルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−n−オクチルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−n−オクチルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−n−ノニルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−n−ノニルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−n−ノニルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−n−ノニルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−n−デシルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−n−デシルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−n−デシルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−n−デシルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−メトキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(3−メトキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−メトキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(5−メトキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−メトキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(7−メトキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−メトキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−エトキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(3−エトキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−エトキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(5−エトキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−エトキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(7−エトキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−エトキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−n−プロポキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(3−n−プロポキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−n−プロポキシナフチル)]メチリデン−5,5−ジメチル−3−
オキソピラゾリジン N,N−ベタイン、1−[1−(5−n−プロポキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−n−プロポキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(7−n−プロポキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−n−プロポキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−iso−プロポキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(3−iso−プロポキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−iso−プロポキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(5−iso−プロポキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−iso−プロポキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(7−iso−プロポキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−iso−プロポキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−n−ブトキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(3−n−ブトキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−n−ブトキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(5−n−ブトキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−n−ブトキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(7−n−ブトキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−n−ブトキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−iso−ブトキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(3−iso−ブトキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−iso−ブトキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(5−iso−ブトキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−iso−ブトキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(7−iso−ブトキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−iso−ブトキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−tert−ブトキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(3−tert−ブトキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−tert−ブトキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(5−tert−ブトキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−tert−ブトキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(7−tert−ブトキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−tert−ブトキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−n−ペントキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−n−ペントキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−n−ペントキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−n−ペントキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−n−ヘキシルオキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−n−ヘキシルオキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−n−ヘキシルオキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−n−ヘキシルオキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−n−ヘプチルオキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−n−ヘプチルオキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−n−ヘプチルオキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−n−ヘプチルオキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−n−オクチルオキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−n−オクチルオキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−n−オクチルオキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−n−オクチルオキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−n−ノニルオキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−n−ノニルオキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、N,N−ベタイン、1−[1−(6−n−ノニルオキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−n−ノニルオキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−n−デシルオキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−n−デシルオキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−n−デシルオキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−n−デシルオキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−フルオロナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(3−フルオロナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−フルオロナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(5−フルオロナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−フルオロナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(7−フルオロナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−フルオロナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−クロロナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(3−クロロナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−クロロナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(5−クロロナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−クロロナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(7−クロロナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−クロロナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−ブロモナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(3−ブロモナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−ブロモナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(5−ブロモナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−ブロモナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(7−ブロモナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−ブロモナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−シアノナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(3−シアノナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−シアノナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(5−シアノナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−シアノナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(7−シアノナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−シアノナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(2−ニトロナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(3−ニトロナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(4−ニトロナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(5−ニトロナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(6−ニトロナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(7−ニトロナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[1−(8−ニトロナフチル)]メチリデン−5,5−ジメチル−
3−オキソピラゾリジン N,N−ベタイン等を挙げることができる。
The N, N-betaine derivative represented by the general formula (2) of the present invention is a 1-naphthyl group which has a 5,5-dimethyl-3-oxopyrazolin skeleton and R 3 may have a substituent. Specific examples include 1- (1-naphthylmethylidene) -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (2-methylnaphthyl) ] Methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (3-methylnaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N -Betaine, 1- [1- (4-methylnaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (5-methylnaphthyl)] methylidene-5 , 5-Dimethyl-3-Oki Pyrazolidine N, N-betaine, 1- [1- (6-methylnaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (7-methylnaphthyl) ] Methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (8-methylnaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N -Betaine, 1- [1- (2-ethylnaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (3-ethylnaphthyl)] methylidene-5 , 5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (4-ethylnaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1 − [ -(5-Ethylnaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (6-ethylnaphthyl)] methylidene-5,5-dimethyl-3- Oxopyrazolidine N, N-betaine, 1- [1- (7-ethylnaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (8- Ethylnaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (2-n-propylnaphthyl)] methylidene-5,5-dimethyl-3-oxopyra Zolidine N, N-betaine, 1- [1- (3-n-propylnaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (4- n-propyl naphthy )] Methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (5-n-propylnaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazo Lysine N, N-betaine, 1- [1- (6-n-propylnaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (7-n -Propylnaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (8-n-propylnaphthyl)] methylidene-5,5-dimethyl-3-oxo Pyrazolidine N, N-betaine, 1- [1- (2-iso-propylnaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (3 -Iso-propyl Butyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (4-iso-propylnaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazo Lysine N, N-betaine, 1- [1- (5-iso-propylnaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (6-iso -Propylnaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (7-iso-propylnaphthyl)] methylidene-5,5-dimethyl-3-oxo Pyrazolidine N, N-betaine, 1- [1- (8-iso-propylnaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- 2-n-butylnaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (3-n-butylnaphthyl)] methylidene-5,5-dimethyl- 3-oxopyrazolidine N, N-betaine, 1- [1- (4-n-butylnaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1 -(5-n-butylnaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (6-n-butylnaphthyl)] methylidene-5,5- Dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (7-n-butylnaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (8-n-butyl Naphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (2-iso-butylnaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazo Lysine N, N-betaine, 1- [1- (3-iso-butylnaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (4-iso -Butylnaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (5-iso-butylnaphthyl)] methylidene-5,5-dimethyl-3-oxo Pyrazolidine N, N-betaine, 1- [1- (6-iso-butylnaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (7 -Is -Butylnaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (8-iso-butylnaphthyl)] methylidene-5,5-dimethyl-3-oxo Pyrazolidine N, N-betaine, 1- [1- (2-tert-butylnaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (3 -Tert-butylnaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (4-tert-butylnaphthyl)] methylidene-5,5-dimethyl-3 -Oxopyrazolidine N, N-betaine, 1- [1- (5-tert-butylnaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1 [1- (6-tert-Butylnaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (7-tert-butylnaphthyl)] methylidene-5 5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (8-tert-butylnaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (2-n-pentylnaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (4-n-pentylnaphthyl)] methylidene- 5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (6-n-pentylnaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N- Solid In, 1- [1- (8-n-pentylnaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (2-n-hexylnaphthyl)] Methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (4-n-hexylnaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (6-n-hexylnaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (8-n-hexylnaphthyl) )] Methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (2-n-heptylnaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-Betai , 1- [1- (4-n-heptylnaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (6-n-heptylnaphthyl)] methylidene -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (8-n-heptylnaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N -Betaine, 1- [1- (2-n-octylnaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (4-n-octylnaphthyl) ] Methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (6-n-octylnaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N , N-betaine 1- [1- (8-n-octylnaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (2-n-nonylnaphthyl)] methylidene- 5,5-Dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (4-n-nonylnaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N- Betaine, 1- [1- (6-n-nonylnaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (8-n-nonylnaphthyl)] Methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (2-n-decylnaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- ( 4-n-decylnaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (6-n-decylnaphthyl)] methylidene-5,5-dimethyl- 3-oxopyrazolidine N, N-betaine, 1- [1- (8-n-decylnaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1 -(2-Methoxynaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (3-methoxynaphthyl)] methylidene-5,5-dimethyl-3- Oxopyrazolidine N, N-betaine, 1- [1- (4-methoxynaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (5- Methoxynaphthyl ] Methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (6-methoxynaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N -Betaine, 1- [1- (7-methoxynaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (8-methoxynaphthyl)] methylidene-5 , 5-Dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (2-ethoxynaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1 -[1- (3-Ethoxynaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (4-ethoxynaphthyl)] methylidene-5,5-di Tyl-3-oxopyrazolidine N, N-betaine, 1- [1- (5-ethoxynaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1 -(6-Ethoxynaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (7-ethoxynaphthyl)] methylidene-5,5-dimethyl-3- Oxopyrazolidine N, N-betaine, 1- [1- (8-ethoxynaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (2- n-propoxynaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (3-n-propoxynaphthyl)] methylidene-5,5-dimethyl-3- Oki Sopyrazolidine N, N-betaine, 1- [1- (4-n-propoxynaphthyl)] methylidene-5,5-dimethyl-3-
Oxopyrazolidine N, N-betaine, 1- [1- (5-n-propoxynaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- ( 6-n-propoxynaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (7-n-propoxynaphthyl)] methylidene-5,5-dimethyl- 3-oxopyrazolidine N, N-betaine, 1- [1- (8-n-propoxynaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1 -(2-iso-propoxynaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (3-iso-propoxynaphthyl)] methylidene-5 -Dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (4-iso-propoxynaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1 -[1- (5-iso-propoxynaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (6-iso-propoxynaphthyl)] methylidene-5 , 5-Dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (7-iso-propoxynaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine 1- [1- (8-iso-propoxynaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (2-n-butoxy) Butyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (3-n-butoxynaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazo Lysine N, N-betaine, 1- [1- (4-n-butoxynaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (5-n -Butoxynaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (6-n-butoxynaphthyl)] methylidene-5,5-dimethyl-3-oxo Pyrazolidine N, N-betaine, 1- [1- (7-n-butoxynaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (8 -N-Butoxynaphth Til)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (2-iso-butoxynaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazo Lysine N, N-betaine, 1- [1- (3-iso-butoxynaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (4-iso -Butoxynaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (5-iso-butoxynaphthyl)] methylidene-5,5-dimethyl-3-oxo Pyrazolidine N, N-betaine, 1- [1- (6-iso-butoxynaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (7 iso-butoxynaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (8-iso-butoxynaphthyl)] methylidene-5,5-dimethyl-3- Oxopyrazolidine N, N-betaine, 1- [1- (2-tert-butoxynaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- ( 3-tert-butoxynaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (4-tert-butoxynaphthyl)] methylidene-5,5-dimethyl- 3-oxopyrazolidine N, N-betaine, 1- [1- (5-tert-butoxynaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N N-betaine, 1- [1- (6-tert-butoxynaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (7-tert-butoxynaphthyl) )] Methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (8-tert-butoxynaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (2-n-pentoxynaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (4-n -Pentoxynaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (6-n-pentoxynaphthyl)] methylidene-5,5-dimethyl-3 − Xopyrazolidine N, N-betaine, 1- [1- (8-n-pentoxynaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (2- n-hexyloxynaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (4-n-hexyloxynaphthyl)] methylidene-5,5-dimethyl- 3-oxopyrazolidine N, N-betaine, 1- [1- (6-n-hexyloxynaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [ 1- (8-n-hexyloxynaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (2-n-heptyloxynaphthyl)] methyl Den-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (4-n-heptyloxynaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N , N-betaine, 1- [1- (6-n-heptyloxynaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (8-n- Heptyloxynaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (2-n-octyloxynaphthyl)] methylidene-5,5-dimethyl-3- Oxopyrazolidine N, N-betaine, 1- [1- (4-n-octyloxynaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (6-n -Octyloxynaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (8-n-octyloxynaphthyl)] methylidene-5,5-dimethyl-3 -Oxopyrazolidine N, N-betaine, 1- [1- (2-n-nonyloxynaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1 -(4-n-nonyloxynaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, N, N-betaine, 1- [1- (6-n-nonyloxynaphthyl) )] Methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (8-n-nonyloxynaphthyl)] methylidene-5,5-dimethyl-3-oxopyra Lysine N, N-betaine, 1- [1- (2-n-decyloxynaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (4- n-decyloxynaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (6-n-decyloxynaphthyl)] methylidene-5,5-dimethyl- 3-oxopyrazolidine N, N-betaine, 1- [1- (8-n-decyloxynaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [ 1- (2-Fluoronaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (3-fluoronaphthyl)] methylidene-5,5-dimethyl-3 -Oxo Pyrazolidine N, N-betaine, 1- [1- (4-fluoronaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (5-fluoronaphthyl) ] Methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (6-fluoronaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N -Betaine, 1- [1- (7-fluoronaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (8-fluoronaphthyl)] methylidene-5 , 5-Dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (2-chloronaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine 1- [1- (3-Chloronaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (4-chloronaphthyl)] methylidene-5,5 -Dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (5-chloronaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [ 1- (6-Chloronaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (7-chloronaphthyl)] methylidene-5,5-dimethyl-3 -Oxopyrazolidine N, N-betaine, 1- [1- (8-chloronaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (2 -Bromonaphthyl)] Liden-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (3-bromonaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N- Betaine, 1- [1- (4-bromonaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (5-bromonaphthyl)] methylidene-5 5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (6-bromonaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (7-bromonaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (8-bromonaphthyl)] methylidene-5,5-dimethyl- 3-oxo Lazolidine N, N-betaine, 1- [1- (2-cyanonaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (3-cyanonaphthyl) ] Methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (4-cyanonaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N -Betaine, 1- [1- (5-cyanonaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (6-cyanonaphthyl)] methylidene-5 , 5-Dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (7-cyanonaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1 -[1 (8-cyanonaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (2-nitronaphthyl)] methylidene-5,5-dimethyl-3-oxo Pyrazolidine N, N-betaine, 1- [1- (3-nitronaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (4-nitro Naphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (5-nitronaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N , N-betaine, 1- [1- (6-nitronaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (7-nitronaphthyl)] methylidene -5 , 5-Dimethyl-3-oxopyrazolidine N, N-betaine, 1- [1- (8-nitronaphthyl)] methylidene-5,5-dimethyl-
3-oxopyrazolidine N, N-betaine and the like can be mentioned.

本発明の一般式(2)で表されるN,N−ベタイン誘導体として、5,5−ジメチル−3−オキソピラゾリン骨格を有し、Rが置換基を有しても良い2−ナフチル基であるものとしては、具体的には例えば、1−(2−ナフチルメチリデン)−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−メチルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(3−メチルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−メチルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(5−メチルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−メチルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(7−メチルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−メチルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−エチルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(3−エチルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−エチルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(5−エチルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−エチルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(7−エチルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−エチルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−n−プロピルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(3−n−プロピルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−n−プロピルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(5−n−プロピルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−n−プロピルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(7−n−プロピルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−n−プロピルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−iso−プロピルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(3−iso−プロピルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−iso−プロピルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(5−iso−プロピルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−iso−プロピルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(7−iso−プロピルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−iso−プロピルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−n−ブチルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(3−n−ブチルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−n−ブチルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(5−n−ブチルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−n−ブチルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(7−n−ブチルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−n−ブチルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−iso−ブチルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(3−iso−ブチルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−iso−ブチルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(5−iso−ブチルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−iso−ブチルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(7−iso−ブチルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−iso−ブチルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−tert−ブチルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(3−tert−ブチルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−tert−ブチルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(5−tert−ブチルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−tert−ブチルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(7−tert−ブチルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−tert−ブチルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−n−ペンチルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−n−ペンチルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−n−ペンチルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−n−ペンチルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−n−ヘキシルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−n−ヘキシルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−n−ヘキシルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−n−ヘキシルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−n−ヘプチルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−n−ヘプチルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−n−ヘプチルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−n−ヘプチルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−n−オクチルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−n−オクチルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−n−オクチルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−n−オクチルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−n−ノニルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−n−ノニルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−n−ノニルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−n−ノニルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−n−デシルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−n−デシルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−n−デシルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−n−デシルナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−メトキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(3−メトキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−メトキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(5−メトキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−メトキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(7−メトキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−メトキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−エトキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(3−エトキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−エトキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(5−エトキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−エトキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(7−エトキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−エトキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−n−プロポキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(3−n−プロポキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−n−プロポキシナフチル)]メチリデン−5,5−ジメチル−3−
オキソピラゾリジン N,N−ベタイン、1−[2−(5−n−プロポキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−n−プロポキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(7−n−プロポキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−n−プロポキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−iso−プロポキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(3−iso−プロポキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−iso−プロポキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(5−iso−プロポキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−iso−プロポキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(7−iso−プロポキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−iso−プロポキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−n−ブトキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(3−n−ブトキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−n−ブトキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(5−n−ブトキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−n−ブトキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(7−n−ブトキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−n−ブトキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−iso−ブトキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(3−iso−ブトキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−iso−ブトキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(5−iso−ブトキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−iso−ブトキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(7−iso−ブトキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−iso−ブトキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−tert−ブトキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(3−tert−ブトキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−tert−ブトキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(5−tert−ブトキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−tert−ブトキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(7−tert−ブトキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−tert−ブトキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−n−ペントキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−n−ペントキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−n−ペントキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−n−ペントキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−n−ヘキシルオキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−n−ヘキシルオキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−n−ヘキシルオキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−n−ヘキシルオキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−n−ヘプチルオキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−n−ヘプチルオキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−n−ヘプチルオキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−n−ヘプチルオキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−n−オクチルオキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−n−オクチルオキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−n−オクチルオキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−n−オクチルオキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−n−ノニルオキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−n−ノニルオキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−n−ノニルオキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−n−ノニルオキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−n−デシルオキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−n−デシルオキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−n−デシルオキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−n−デシルオキシナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−フルオロナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(3−フルオロナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−フルオロナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(5−フルオロナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−フルオロナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(7−フルオロナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−フルオロナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−クロロナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(3−クロロナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−クロロナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(5−クロロナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−クロロナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(7−クロロナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−クロロナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−ブロモナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(3−ブロモナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−ブロモナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(5−ブロモナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−ブロモナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(7−ブロモナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−ブロモナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−シアノナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(3−シアノナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−シアノナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(5−シアノナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−シアノナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(7−シアノナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−シアノナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(1−ニトロナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(3−ニトロナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−ニトロナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(5−ニトロナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(6−ニトロナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(7−ニトロナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(8−ニトロナフチル)]メチリデン−5,5−ジメチル−3−オキソピラゾリ
ジン N,N−ベタイン等を挙げることができる。
The N, N-betaine derivative represented by the general formula (2) of the present invention is a 2-naphthyl group having a 5,5-dimethyl-3-oxopyrazoline skeleton, and R 3 may have a substituent. Specific examples include 1- (2-naphthylmethylidene) -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (1-methylnaphthyl) ] Methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (3-methylnaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N -Betaine, 1- [2- (4-methylnaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (5-methylnaphthyl)] methylidene-5 , 5-Dimethyl-3-oki Pyrazolidine N, N-betaine, 1- [2- (6-methylnaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (7-methylnaphthyl) ] Methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (8-methylnaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N -Betaine, 1- [2- (1-ethylnaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (3-ethylnaphthyl)] methylidene-5 , 5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (4-ethylnaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1 − [ -(5-Ethylnaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (6-ethylnaphthyl)] methylidene-5,5-dimethyl-3- Oxopyrazolidine N, N-betaine, 1- [2- (7-ethylnaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (8- Ethylnaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (1-n-propylnaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazine Zolidine N, N-betaine, 1- [2- (3-n-propylnaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (4- n-propyl naphthy )] Methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (5-n-propylnaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazo Lysine N, N-betaine, 1- [2- (6-n-propylnaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (7-n -Propylnaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (8-n-propylnaphthyl)] methylidene-5,5-dimethyl-3-oxo Pyrazolidine N, N-betaine, 1- [2- (1-iso-propylnaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (3 -Iso-propyl Butyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (4-iso-propylnaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazo Lysine N, N-betaine, 1- [2- (5-iso-propylnaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (6-iso -Propylnaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (7-iso-propylnaphthyl)] methylidene-5,5-dimethyl-3-oxo Pyrazolidine N, N-betaine, 1- [2- (8-iso-propylnaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- 1-n-butylnaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (3-n-butylnaphthyl)] methylidene-5,5-dimethyl- 3-oxopyrazolidine N, N-betaine, 1- [2- (4-n-butylnaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2 -(5-n-butylnaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (6-n-butylnaphthyl)] methylidene-5,5- Dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (7-n-butylnaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (8-n-butyl Naphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (1-iso-butylnaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazo Lysine N, N-betaine, 1- [2- (3-iso-butylnaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (4-iso -Butylnaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (5-iso-butylnaphthyl)] methylidene-5,5-dimethyl-3-oxo Pyrazolidine N, N-betaine, 1- [2- (6-iso-butylnaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (7 -Is -Butylnaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (8-iso-butylnaphthyl)] methylidene-5,5-dimethyl-3-oxo Pyrazolidine N, N-betaine, 1- [2- (1-tert-butylnaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (3 -Tert-butylnaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (4-tert-butylnaphthyl)] methylidene-5,5-dimethyl-3 -Oxopyrazolidine N, N-betaine, 1- [2- (5-tert-butylnaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1 [2- (6-tert-Butylnaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (7-tert-butylnaphthyl)] methylidene-5 5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (8-tert-butylnaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (1-n-pentylnaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (4-n-pentylnaphthyl)] methylidene- 5,5-Dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (6-n-pentylnaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N- Solid In, 1- [2- (8-n-pentylnaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (1-n-hexylnaphthyl)] Methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (4-n-hexylnaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (6-n-hexylnaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (8-n-hexylnaphthyl) )] Methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (1-n-heptylnaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-Betai , 1- [2- (4-n-heptylnaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (6-n-heptylnaphthyl)] methylidene -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (8-n-heptylnaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N -Betaine, 1- [2- (1-n-octylnaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (4-n-octylnaphthyl) ] Methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (6-n-octylnaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N , N-betaine 1- [2- (8-n-octylnaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (1-n-nonylnaphthyl)] methylidene- 5,5-Dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (4-n-nonylnaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N- Betaine, 1- [2- (6-n-nonylnaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (8-n-nonylnaphthyl)] Methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (1-n-decylnaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- ( 4-n-decylnaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (6-n-decylnaphthyl)] methylidene-5,5-dimethyl- 3-oxopyrazolidine N, N-betaine, 1- [2- (8-n-decylnaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2 -(1-methoxynaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (3-methoxynaphthyl)] methylidene-5,5-dimethyl-3- Oxopyrazolidine N, N-betaine, 1- [2- (4-methoxynaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (5- Methoxynaphthyl ] Methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (6-methoxynaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N -Betaine, 1- [2- (7-methoxynaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (8-methoxynaphthyl)] methylidene-5 , 5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (1-ethoxynaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1 -[2- (3-Ethoxynaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (4-ethoxynaphthyl)] methylidene-5,5-di Tyl-3-oxopyrazolidine N, N-betaine, 1- [2- (5-ethoxynaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2 -(6-Ethoxynaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (7-ethoxynaphthyl)] methylidene-5,5-dimethyl-3- Oxopyrazolidine N, N-betaine, 1- [2- (8-ethoxynaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (1- n-propoxynaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (3-n-propoxynaphthyl)] methylidene-5,5-dimethyl-3- Oki Sopyrazolidine N, N-betaine, 1- [2- (4-n-propoxynaphthyl)] methylidene-5,5-dimethyl-3-
Oxopyrazolidine N, N-betaine, 1- [2- (5-n-propoxynaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- ( 6-n-propoxynaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (7-n-propoxynaphthyl)] methylidene-5,5-dimethyl- 3-oxopyrazolidine N, N-betaine, 1- [2- (8-n-propoxynaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2 -(1-iso-propoxynaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (3-iso-propoxynaphthyl)] methylidene-5 -Dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (4-iso-propoxynaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1 -[2- (5-iso-propoxynaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (6-iso-propoxynaphthyl)] methylidene-5 , 5-Dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (7-iso-propoxynaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine 1- [2- (8-iso-propoxynaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (1-n-butoxy) Butyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (3-n-butoxynaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazo Lysine N, N-betaine, 1- [2- (4-n-butoxynaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (5-n -Butoxynaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (6-n-butoxynaphthyl)] methylidene-5,5-dimethyl-3-oxo Pyrazolidine N, N-betaine, 1- [2- (7-n-butoxynaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (8 -N-Butoxynaphth Til)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (1-iso-butoxynaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazo Lysine N, N-betaine, 1- [2- (3-iso-butoxynaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (4-iso -Butoxynaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (5-iso-butoxynaphthyl)] methylidene-5,5-dimethyl-3-oxo Pyrazolidine N, N-betaine, 1- [2- (6-iso-butoxynaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (7 iso-butoxynaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (8-iso-butoxynaphthyl)] methylidene-5,5-dimethyl-3- Oxopyrazolidine N, N-betaine, 1- [2- (1-tert-butoxynaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- ( 3-tert-butoxynaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (4-tert-butoxynaphthyl)] methylidene-5,5-dimethyl- 3-oxopyrazolidine N, N-betaine, 1- [2- (5-tert-butoxynaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N N-betaine, 1- [2- (6-tert-butoxynaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (7-tert-butoxynaphthyl) )] Methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (8-tert-butoxynaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (1-n-pentoxynaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (4-n -Pentoxynaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (6-n-pentoxynaphthyl)] methylidene-5,5-dimethyl-3 − Xopyrazolidine N, N-betaine, 1- [2- (8-n-pentoxynaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (1- n-hexyloxynaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (4-n-hexyloxynaphthyl)] methylidene-5,5-dimethyl- 3-oxopyrazolidine N, N-betaine, 1- [2- (6-n-hexyloxynaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [ 2- (8-n-hexyloxynaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (1-n-heptyloxynaphthyl)] methyl Den-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (4-n-heptyloxynaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N , N-betaine, 1- [2- (6-n-heptyloxynaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (8-n- Heptyloxynaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (1-n-octyloxynaphthyl)] methylidene-5,5-dimethyl-3- Oxopyrazolidine N, N-betaine, 1- [2- (4-n-octyloxynaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (6-n -Octyloxynaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (8-n-octyloxynaphthyl)] methylidene-5,5-dimethyl-3 -Oxopyrazolidine N, N-betaine, 1- [2- (1-n-nonyloxynaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2 -(4-n-nonyloxynaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (6-n-nonyloxynaphthyl)] methylidene-5 5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (8-n-nonyloxynaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-beta In, 1- [2- (1-n-decyloxynaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (4-n-decyloxynaphthyl) )] Methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (6-n-decyloxynaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazo Lysine N, N-betaine, 1- [2- (8-n-decyloxynaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (1- Fluoronaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (3-fluoronaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, -Betaine, 1- [2- (4-fluoronaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (5-fluoronaphthyl)] methylidene-5 , 5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (6-fluoronaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1 -[2- (7-Fluoronaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (8-fluoronaphthyl)] methylidene-5,5-dimethyl -3-Oxopyrazolidine N, N-betaine, 1- [2- (1-chloronaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (3- Chloronaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (4-chloronaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (5-chloronaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (6-chloronaphthyl)] Methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (7-chloronaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N- Betaine, 1- [2- (8-chloronaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (1-bromonaphthyl)] methylidene-5 5- Methyl-3-oxopyrazolidine N, N-betaine, 1- [2- (3-bromonaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2 -(4-Bromonaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (5-bromonaphthyl)] methylidene-5,5-dimethyl-3- Oxopyrazolidine N, N-betaine, 1- [2- (6-bromonaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (7- Bromonaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (8-bromonaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N Betaine, 1- [2- (1-cyanonaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (3-cyanonaphthyl)] methylidene-5 5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (4-cyanonaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (5-Cyanonaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (6-cyanonaphthyl)] methylidene-5,5-dimethyl- 3-oxopyrazolidine N, N-betaine, 1- [2- (7-cyanonaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- ( 8-cyanonaphth L)] Methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (1-nitronaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N , N-betaine, 1- [2- (3-nitronaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (4-nitronaphthyl)] methylidene -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (5-nitronaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine , 1- [2- (6-nitronaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (7-nitronaphthyl)] methylidene-5,5 -Dimethyl-3 -Oxopyrazolidine N, N-betaine, 1- [2- (8-nitronaphthyl)] methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine and the like can be mentioned.

本発明の一般式(2)で表されるN,N−ベタイン誘導体として、5,5−ジメチル−3−オキソピラゾリン骨格を有し、Rが置換基を有しても良いアリールエチレニル基であるものとしては、具体的には例えば、1−(3−フェニルプロピリデン−2−エン)−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(2−メチルフェニル)プロピリデン−2−エン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(3−メチルフェニル)プロピリデン−2−エン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(4−メチルフェニル)プロピリデン−2−エン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(2−エチルフェニル)プロピリデン−2−エン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(3−エチルフェニル)プロピリデン−2−エン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(4−エチルフェニル)プロピリデン−2−エン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(2−n−プロピルフェニル)プロピリデン−2−エン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(3−n−プロピルフェニル)プロピリデン−2−エン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(4−n−プロピルフェニル)プロピリデン−2−エン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(2−iso−プロピルフェニル)プロピリデン−2−エン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(3−iso−プロピルフェニル)プロピリデン−2−エン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(4−iso−プロピルフェニル)プロピリデン−2−エン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(2−n−ブチルフェニル)プロピリデン−2−エン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(3−n−ブチルフェニル)プロピリデン−2−エン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(4−n−ブチルフェニル)プロピリデン−2−エン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(2−sec−ブチルフェニル)プロピリデン−2−エン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(3−sec−ブチルフェニル)プロピリデン−2−エン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(4−sec−ブチルフェニル)プロピリデン−2−エン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(2−tert−ブチルフェニル)プロピリデン−2−エン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(3−tert−ブチルフェニル)プロピリデン−2−エン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(4−tert−ブチルフェニル)プロピリデン−2−エン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(2−メトキシフェニル)プロピリデン−2−エン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(3−メトキシフェニル)プロピリデン−2−エン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(4−メトキシフェニル)プロピリデン−2−エン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(2−エトキシフェニル)プロピリデン−2−エン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(3−エトキシフェニル)プロピリデン−2−エン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(4−エトキシフェニル)プロピリデン−2−エン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(2−n−プロポキシフェニル)プロピリデン−2−エン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(3−n−プロポキシフェニル)プロピリデン−2−エン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(4−n−プロポキシフェニル)プロピリデン−2−エン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(2−iso−プロポキシフェニル)プロピリデン−2−エン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(3−iso−プロポキシフェニル)プロピリデン−2−エン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(4−iso−プロポキシフェニル)プロピリデン−2−エン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(2−n−ブトキシフェニル)プロピリデン−2−エン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(3−n−ブトキシフェニル)プロピリデン−2−エン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(4−n−ブトキシフェニル)プロピリデン−2−エン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(2−sec−ブトキシフェニル)プロピリデン−2−エン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(3−sec−ブトキシフェニル)プロピリデン−2−エン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(4−sec−ブトキシフェニル)プロピリデン−2−エン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(2−tert−ブトキシフェニル)プロピリデン−2−エン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(3−tert−ブトキシフェニル)プロピリデン−2−エン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(4−tert−ブトキシフェニル)プロピリデン−2−エン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(2−フルオロフェニル)プロピリデン−2−エン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(3−フルオロフェニル)プロピリデン−2−エン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(4−フルオロフェニル)プロピリデン−2−エン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(2−クロロフェニル)プロピリデン−2−エン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(3−クロロフェニル)プロピリデン−2−エン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(4−クロロフェニル)プロピリデン−2−エン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(2−ブロモフェニル)プロピリデン−2−エン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(3−ブロモフェニル)プロピリデン−2−エン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(4−ブロモフェニル)プロピリデン−2−エン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(2−シアノフェニル)プロピリデン−2−エン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(3−シアノフェニル)プロピリデン−2−エン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(4−シアノフェニル)プロピリデン−2−エン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(2−ニトロフェニル)プロピリデン−2−エン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(3−ニトロフェニル)プロピリデン−2−エン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(4−ニトロフェニル)プロピリデン−2−エン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン等を挙げることができる。 As an N, N-betaine derivative represented by the general formula (2) of the present invention, an arylethylenyl group having a 5,5-dimethyl-3-oxopyrazoline skeleton, and R 3 may have a substituent. Specific examples include 1- (3-phenylpropylidene-2-ene) -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [3- (2- Methylphenyl) propylidene-2-ene] -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [3- (3-methylphenyl) propylidene-2-ene] -5,5- Dimethyl-3-oxopyrazolidine N, N-betaine, 1- [3- (4-methylphenyl) propylidene-2-ene] -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [3- (2-D Ruphenyl) propylidene-2-ene] -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [3- (3-ethylphenyl) propylidene-2-ene] -5,5-dimethyl -3-oxopyrazolidine N, N-betaine, 1- [3- (4-ethylphenyl) propylidene-2-ene] -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1 -[3- (2-n-propylphenyl) propylidene-2-ene] -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [3- (3-n-propylphenyl) Propylidene-2-ene] -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [3- (4-n-propylphenyl) propylidene-2-ene] -5,5-dimethyl -3-Oki Pyrazolidine N, N-betaine, 1- [3- (2-iso-propylphenyl) propylidene-2-ene] -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [3- (3-Iso-propylphenyl) propylidene-2-ene] -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [3- (4-iso-propylphenyl) propylidene-2- Ene] -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [3- (2-n-butylphenyl) propylidene-2-ene] -5,5-dimethyl-3-oxo Pyrazolidine N, N-betaine, 1- [3- (3-n-butylphenyl) propylidene-2-ene] -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [ 3- ( -N-butylphenyl) propylidene-2-ene] -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [3- (2-sec-butylphenyl) propylidene-2-ene] -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [3- (3-sec-butylphenyl) propylidene-2-ene] -5,5-dimethyl-3-oxopyrazo Lysine N, N-betaine, 1- [3- (4-sec-butylphenyl) propylidene-2-ene] -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [3- (2-tert-Butylphenyl) propylidene-2-ene] -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [3- (3-tert-butylphenyl) propylidene-2 Ene] -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [3- (4-tert-butylphenyl) propylidene-2-ene] -5,5-dimethyl-3-oxo Pyrazolidine N, N-betaine, 1- [3- (2-methoxyphenyl) propylidene-2-ene] -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [3- (3-methoxyphenyl) propylidene-2-ene] -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [3- (4-methoxyphenyl) propylidin-2-ene] -5 , 5-Dimethyl-3-oxopyrazolidine N, N-betaine, 1- [3- (2-ethoxyphenyl) propylidene-2-ene] -5,5-dimethyl-3-oxopyrazolidine N, N -Betai 1- [3- (3-Ethoxyphenyl) propylidene-2-ene] -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [3- (4-ethoxyphenyl) propylidene- 2-ene] -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [3- (2-n-propoxyphenyl) propylidene-2-ene] -5,5-dimethyl-3 -Oxopyrazolidine N, N-betaine, 1- [3- (3-n-propoxyphenyl) propylidin-2-ene] -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1 -[3- (4-n-propoxyphenyl) propylidene-2-ene] -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [3- (2-iso-propoxyphenyl) Propyri N-2-ene] -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [3- (3-iso-propoxyphenyl) propylidene-2-ene] -5,5-dimethyl -3-oxopyrazolidine N, N-betaine, 1- [3- (4-iso-propoxyphenyl) propylidene-2-ene] -5,5-dimethyl-3-oxopyrazolidine N, N-betaine 1- [3- (2-n-butoxyphenyl) propylidene-2-ene] -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [3- (3-n-butoxy Phenyl) propylidene-2-ene] -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [3- (4-n-butoxyphenyl) propylidene-2-ene] -5,5 -Dimethyl-3-o Xopyrazolidine N, N-betaine, 1- [3- (2-sec-butoxyphenyl) propylidene-2-ene] -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [3- (3-sec-butoxyphenyl) propylidene-2-ene] -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [3- (4-sec-butoxyphenyl) propylidene-2- Ene] -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [3- (2-tert-butoxyphenyl) propylidene-2-ene] -5,5-dimethyl-3-oxo Pyrazolidine N, N-betaine, 1- [3- (3-tert-butoxyphenyl) propylidene-2-ene] -5,5-dimethyl-3-oxopyrazolidine N, N-beta 1- [3- (4-tert-butoxyphenyl) propylidene-2-ene] -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [3- (2-fluorophenyl) ) Propylidene-2-ene] -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [3- (3-fluorophenyl) propylidene-2-ene] -5,5-dimethyl- 3-oxopyrazolidine N, N-betaine, 1- [3- (4-fluorophenyl) propylidene-2-ene] -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [3- (2-Chlorophenyl) propylidene-2-ene] -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [3- (3-chlorophenyl) propylidene-2-ene]- 5 , 5-Dimethyl-3-oxopyrazolidine N, N-betaine, 1- [3- (4-chlorophenyl) propylidene-2-ene] -5,5-dimethyl-3-oxopyrazolidine N, N- Betaine, 1- [3- (2-bromophenyl) propylidene-2-ene] -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [3- (3-bromophenyl) propylidene -2-ene] -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [3- (4-bromophenyl) propylidene-2-ene] -5,5-dimethyl-3- Oxopyrazolidine N, N-betaine, 1- [3- (2-cyanophenyl) propylidene-2-ene] -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [3 -(3-Cyanofe L) propylidene-2-ene] -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [3- (4-cyanophenyl) propylidene-2-ene] -5,5-dimethyl -3-oxopyrazolidine N, N-betaine, 1- [3- (2-nitrophenyl) propylidene-2-ene] -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1 -[3- (3-Nitrophenyl) propylidene-2-ene] -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [3- (4-nitrophenyl) propylidene-2- Ene] -5,5-dimethyl-3-oxopyrazolidine N, N-betaine and the like.

本発明の一般式(2)で表されるN,N−ベタイン誘導体として、5,5−ジメチル−3−オキソピラゾリン骨格を有し、Rが置換基を有しても良いアリールアルキル基であるものとしては、具体的には例えば、1−(2−フェニルエチリデン)−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(3−フェニルプロピリデン)−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(4−フェニルブチリデン)−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(5−フェニルペンチリデン)−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−(6−フェニルヘキシリデン)−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(2−メチルフェニル)エチリデン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(3−メチルフェニル)エチリデン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−メチルフェニル)エチリデン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(2−メチルフェニル)プロピリデン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(3−メチルフェニル)プロピリデン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(4−メチルフェニル)プロピリデン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[4−(2−メチルフェニル)ブチリデン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[4−(3−メチルフェニル)ブチリデン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[4−(4−メチルフェニル)ブチリデン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[5−(2−メチルフェニル)ペンチリデン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[5−(3−メチルフェニル)ペンチリデン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[5−(4−メチルフェニル)ペンチリデン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(2−エチルフェニル)エチリデン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(3−エチルフェニル)エチリデン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−エチルフェニル)エチリデン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(2−エチルフェニル)プロピリデン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(3−エチルフェニル)プロピリデン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(4−エチルフェニル)プロピリデン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[4−(2−エチルフェニル)ブチリデン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[4−(3−エチルフェニル)ブチリデン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[4−(4−エチルフェニル)ブチリデン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[5−(2−エチルフェニル)ペンチリデン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[5−(3−エチルフェニル)ペンチリデン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[5−(4−エチルフェニル)ペンチリデン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(2−メトキシフェニル)エチリデン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(3−メトキシフェニル)エチリデン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−メトキシフェニル)エチリデン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(2−メトキシフェニル)プロピリデン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(3−メトキシフェニル)プロピリデン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(4−メトキシフェニル)プロピリデン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[4−(2−メトキシフェニル)ブチリデン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[4−(3−メトキシフェニル)ブチリデン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[4−(4−メトキシフェニル)ブチリデン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[5−(2−メトキシフェニル)ペンチリデン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[5−(3−メトキシフェニル)ペンチリデン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[5−(4−メトキシフェニル)ペンチリデン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(2−エトキシフェニル)エチリデン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(3−エトキシフェニル)エチリデン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−エトキシフェニル)エチリデン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(2−エトキシフェニル)プロピリデン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(3−エトキシフェニル)プロピリデン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(4−エトキシフェニル)プロピリデン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[4−(2−エトキシフェニル)ブチリデン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[4−(3−エトキシフェニル)ブチリデン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[4−(4−エトキシフェニル)ブチリデン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[5−(2−エトキシフェニル)ペンチリデン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[5−(3−エトキシフェニル)ペンチリデン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[5−(4−エトキシフェニル)ペンチリデン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(2−フルオロフェニル)エチリデン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(3−フルオロフェニル)エチリデン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−フルオロフェニル)エチリデン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(2−フルオロフェニル)プロピリデン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(3−フルオロフェニル)プロピリデン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(4−フルオロフェニル)プロピリデン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[4−(2−フルオロフェニル)ブチリデン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[4−(3−フルオロフェニル)ブチリデン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[4−(4−フルオロフェニル)ブチリデン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[5−(2−フルオロフェニル)ペンチリデン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[5−(3−フルオロフェニル)ペンチリデン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[5−(4−フルオロフェニル)ペンチリデン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(2−クロロフェニル)エチリデン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(3−クロロフェニル)エチリデン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−クロロフェニル)エチリデン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(2−クロロフェニル)プロピリデン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(3−クロロフェニル)プロピリデン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(4−クロロフェニル)プロピリデン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[4−(2−クロロフェニル)ブチリデン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[4−(3−クロロフェニル)ブチリデン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[4−(4−クロロフェニル)ブチリデン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[5−(2−クロロフェニル)ペンチリデン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[5−(3−クロロフェニル)ペンチリデン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[5−(4−クロロフェニル)ペンチリデン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(2−ブロモフェニル)エチリデン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(3−ブロモフェニル)エチリデン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−ブロモフェニル)エチリデン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(2−ブロモフェニル)プロピリデン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(3−ブロモフェニル)プロピリデン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(4−ブロモフェニル)プロピリデン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[4−(2−ブロモフェニル)ブチリデン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[4−(3−ブロモフェニル)ブチリデン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[4−(4−ブロモフェニル)ブチリデン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[5−(2−ブロモフェニル)ペンチリデン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[5−(3−ブロモフェニル)ペンチリデン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[5−(4−ブロモフェニル)ペンチリデン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(2−シアノフェニル)エチリデン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(3−シアノフェニル)エチリデン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−シアノフェニル)エチリデン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(2−シアノフェニル)プロピリデン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(3−シアノフェニル)プロピリデン]−5,5−ジメチル−3−オキソピラゾリ
ジン N,N−ベタイン、1−[3−(4−シアノフェニル)プロピリデン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[4−(2−シアノフェニル)ブチリデン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[4−(3−シアノフェニル)ブチリデン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[4−(4−シアノフェニル)ブチリデン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[5−(2−シアノフェニル)ペンチリデン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[5−(3−シアノフェニル)ペンチリデン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[5−(4−シアノフェニル)ペンチリデン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(2−ニトロフェニル)エチリデン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(3−ニトロフェニル)エチリデン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[2−(4−ニトロフェニル)エチリデン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(2−ニトロフェニル)プロピリデン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(3−ニトロフェニル)プロピリデン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[3−(4−ニトロフェニル)プロピリデン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[4−(2−ニトロフェニル)ブチリデン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[4−(3−ニトロフェニル)ブチリデン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[4−(4−ニトロフェニル)ブチリデン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[5−(2−ニトロフェニル)ペンチリデン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[5−(3−ニトロフェニル)ペンチリデン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、1−[5−(4−ニトロフェニル)ペンチリデン]−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、等を挙げることができる。
The N, N-betaine derivative represented by the general formula (2) of the present invention is an arylalkyl group having a 5,5-dimethyl-3-oxopyrazolin skeleton and R 3 which may have a substituent. Specifically, for example, 1- (2-phenylethylidene) -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- (3-phenylpropylidene) -5,5- Dimethyl-3-oxopyrazolidine N, N-betaine, 1- (4-phenylbutylidene) -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- (5-phenylpentylidene ) -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- (6-phenylhexylidene) -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1 − [2- (2 Methylphenyl) ethylidene] -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (3-methylphenyl) ethylidene] -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (4-methylphenyl) ethylidene] -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [3- (2-methylphenyl) propylidene ] -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [3- (3-methylphenyl) propylidene] -5,5-dimethyl-3-oxopyrazolidine N, N- Betaine, 1- [3- (4-methylphenyl) propylidene] -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [4- (2-methylphenyl) butylidene]- , 5-Dimethyl-3-oxopyrazolidine N, N-betaine, 1- [4- (3-methylphenyl) butylidene] -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1 -[4- (4-Methylphenyl) butylidene] -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [5- (2-methylphenyl) pentylidene] -5,5-dimethyl -3-oxopyrazolidine N, N-betaine, 1- [5- (3-methylphenyl) pentylidene] -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [5- (4-Methylphenyl) pentylidene] -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (2-ethylphenyl) ethylidene] -5,5-dimethyl-3-oxopyrazo Lysine N, N-betaine, 1- [2- (3-ethylphenyl) ethylidene] -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (4-ethylphenyl) Ethylidene] -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [3- (2-ethylphenyl) propylidene] -5,5-dimethyl-3-oxopyrazolidine N, N -Betaine, 1- [3- (3-ethylphenyl) propylidene] -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [3- (4-ethylphenyl) propylidene] -5 , 5-Dimethyl-3-oxopyrazolidine N, N-betaine, 1- [4- (2-ethylphenyl) butylidene] -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1 -[4 -(3-Ethylphenyl) butylidene] -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [4- (4-ethylphenyl) butylidene] -5,5-dimethyl-3- Oxopyrazolidine N, N-betaine, 1- [5- (2-ethylphenyl) pentylidene] -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [5- (3- Ethylphenyl) pentylidene] -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [5- (4-ethylphenyl) pentylidene] -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (2-methoxyphenyl) ethylidene] -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (3-methoxyphenyl) ethyl Den] -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (4-methoxyphenyl) ethylidene] -5,5-dimethyl-3-oxopyrazolidine N, N -Betaine, 1- [3- (2-methoxyphenyl) propylidene] -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [3- (3-methoxyphenyl) propylidene] -5 , 5-Dimethyl-3-oxopyrazolidine N, N-betaine, 1- [3- (4-methoxyphenyl) propylidene] -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1 -[4- (2-methoxyphenyl) butylidene] -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [4- (3-methoxyphenyl) butylidene] -5,5-di Tyl-3-oxopyrazolidine N, N-betaine, 1- [4- (4-methoxyphenyl) butylidene] -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [5 -(2-Methoxyphenyl) pentylidene] -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [5- (3-methoxyphenyl) pentylidene] -5,5-dimethyl-3- Oxopyrazolidine N, N-betaine, 1- [5- (4-methoxyphenyl) pentylidene] -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (2- Ethoxyphenyl) ethylidene] -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (3-ethoxyphenyl) ethylidene] -5,5-dimethyl-3-oxopyra Zolidine N, N-betaine, 1- [2- (4-ethoxyphenyl) ethylidene] -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [3- (2-ethoxyphenyl) Propylidene] -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [3- (3-ethoxyphenyl) propylidene] -5,5-dimethyl-3-oxopyrazolidine N, N -Betaine, 1- [3- (4-ethoxyphenyl) propylidene] -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [4- (2-ethoxyphenyl) butylidene] -5 , 5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [4- (3-ethoxyphenyl) butylidene] -5,5-dimethyl-3-oxopyrazolidine N, N-beta In, 1- [4- (4-ethoxyphenyl) butylidene] -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [5- (2-ethoxyphenyl) pentylidene] -5 5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [5- (3-ethoxyphenyl) pentylidene] -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [5- (4-Ethoxyphenyl) pentylidene] -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (2-fluorophenyl) ethylidene] -5,5-dimethyl- 3-oxopyrazolidine N, N-betaine, 1- [2- (3-fluorophenyl) ethylidene] -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- ( 4 Fluorophenyl) ethylidene] -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [3- (2-fluorophenyl) propylidene] -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [3- (3-fluorophenyl) propylidene] -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [3- (4-fluorophenyl) propylidene ] -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [4- (2-fluorophenyl) butylidene] -5,5-dimethyl-3-oxopyrazolidine N, N- Betaine, 1- [4- (3-fluorophenyl) butylidene] -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [4- (4-fluorophenyl) Tylidene] -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [5- (2-fluorophenyl) pentylidene] -5,5-dimethyl-3-oxopyrazolidine N, N -Betaine, 1- [5- (3-fluorophenyl) pentylidene] -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [5- (4-fluorophenyl) pentylidene] -5 , 5-Dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (2-chlorophenyl) ethylidene] -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (3-Chlorophenyl) ethylidene] -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (4-chlorophenyl) ethylidene] -5,5-dimethyl Lu-3-oxopyrazolidine N, N-betaine, 1- [3- (2-chlorophenyl) propylidene] -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [3- (3-Chlorophenyl) propylidene] -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [3- (4-chlorophenyl) propylidene] -5,5-dimethyl-3-oxopyrazo Lysine N, N-betaine, 1- [4- (2-chlorophenyl) butylidene] -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [4- (3-chlorophenyl) butylidene] -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [4- (4-chlorophenyl) butylidene] -5,5-dimethyl-3-oxopyrazolidine N, N -Betaine, 1- [5- (2-chlorophenyl) pentylidene] -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [5- (3-chlorophenyl) pentylidene] -5,5 -Dimethyl-3-oxopyrazolidine N, N-betaine, 1- [5- (4-chlorophenyl) pentylidene] -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2 -(2-Bromophenyl) ethylidene] -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (3-bromophenyl) ethylidene] -5,5-dimethyl-3- Oxopyrazolidine N, N-betaine, 1- [2- (4-bromophenyl) ethylidene] -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [3- (2- Bro Phenyl) propylidene] -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [3- (3-bromophenyl) propylidene] -5,5-dimethyl-3-oxopyrazolidine N , N-betaine, 1- [3- (4-bromophenyl) propylidene] -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [4- (2-bromophenyl) butylidene] -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [4- (3-bromophenyl) butylidene] -5,5-dimethyl-3-oxopyrazolidine N, N-betaine 1- [4- (4-Bromophenyl) butylidene] -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [5- (2-bromophenyl) pentylidene] -5 -Dimethyl-3-oxopyrazolidine N, N-betaine, 1- [5- (3-bromophenyl) pentylidene] -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [ 5- (4-Bromophenyl) pentylidene] -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (2-cyanophenyl) ethylidene] -5,5-dimethyl-3 -Oxopyrazolidine N, N-betaine, 1- [2- (3-cyanophenyl) ethylidene] -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (4 -Cyanophenyl) ethylidene] -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [3- (2-cyanophenyl) propylidene] -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [3- (3-cyanophenyl) propylidene] -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [3- (4-cyanophenyl) Propylidene] -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [4- (2-cyanophenyl) butylidene] -5,5-dimethyl-3-oxopyrazolidine N, N -Betaine, 1- [4- (3-cyanophenyl) butylidene] -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [4- (4-cyanophenyl) butylidene] -5 , 5-Dimethyl-3-oxopyrazolidine N, N-betaine, 1- [5- (2-cyanophenyl) pentylidene] -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1 -[5- ( 3-cyanophenyl) pentylidene] -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [5- (4-cyanophenyl) pentylidene] -5,5-dimethyl-3-oxopyra Zolidine N, N-betaine, 1- [2- (2-nitrophenyl) ethylidene] -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (3-nitrophenyl) ) Ethylidene] -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [2- (4-nitrophenyl) ethylidene] -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [3- (2-nitrophenyl) propylidene] -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [3- (3-nitrophenyl) propylidene -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [3- (4-nitrophenyl) propylidene] -5,5-dimethyl-3-oxopyrazolidine N, N-betaine 1- [4- (2-nitrophenyl) butylidene] -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [4- (3-nitrophenyl) butylidene] -5,5 -Dimethyl-3-oxopyrazolidine N, N-betaine, 1- [4- (4-nitrophenyl) butylidene] -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [ 5- (2-Nitrophenyl) pentylidene] -5,5-dimethyl-3-oxopyrazolidine N, N-betaine, 1- [5- (3-nitrophenyl) pentylidene] -5,5-dimethyl-3 -Oxo Razorijin N, N-betaine, 1- [5- (4-nitrophenyl) pentylidene] -5,5-dimethyl-3-oxo-pyrazolidine N, N-betaine, and the like.

本発明の一般式(3)で表わされるキラル相間移動触媒としては、具体的には例えば、N−ベンジルシンコニニウムブロマイド、N−(2−メチルフェニル)メチルシンコニニウムブロマイド、N−(3−メチルフェニル)メチルシンコニニウムブロマイド、N−(4−メチルフェニル)メチルシンコニニウムブロマイド、N−(3,5−ジメチルフェニル)メチルシンコニニウムブロマイド、N−(2−エチルフェニル)メチルシンコニニウムブロマイド、N−(3−エチルフェニル)メチルシンコニニウムブロマイド、N−(4−エチルフェニル)メチルシンコニニウムブロマイド、N−(3,5−ジエチルフェニル)メチルシンコニニウムブロマイド、N−(2−n−プロピルフェニル)メチルシンコニニウムブロマイド、N−(3−n−プロピルフェニル)メチルシンコニニウムブロマイド、N−(4−n−プロピルフェニル)メチルシンコニニウムブロマイド、N−(3,5−ジ−n−プロピルフェニル)メチルシンコニニウムブロマイド、N−(2−iso−プロピルフェニル)メチルシンコニニウムブロマイド、N−(3−iso−プロピルフェニル)メチルシンコニニウムブロマイド、N−(4−iso−プロピルフェニル)メチルシンコニニウムブロマイド、N−(3,5−ジ−iso−プロピルフェニル)メチルシンコニニウムブロマイド、N−(2−n−ブチルフェニル)メチルシンコニニウムブロマイド、N−(3−n−ブチルフェニル)メチルシンコニニウムブロマイド、N−(4−n−ブチルフェニル)メチルシンコニニウムブロマイド、N−(3,5−ジ−n−ブチルフェニル)メチルシンコニニウムブロマイド、N−(2−tert−ブチルフェニル)メチルシンコニニウムブロマイド、N−(3−tert−ブチルフェニル)メチルシンコニニウムブロマイド、N−(4−tert−ブチルフェニル)メチルシンコニニウムブロマイド、N−(3,5−ジ−tert−ブチルフェニル)メチルシンコニニウムブロマイド、N−(2−メトキシフェニル)メチルシンコニニウムブロマイド、N−(3−メトキシフェニル)メチルシンコニニウムブロマイド、N−(4−メトキシフェニル)メチルシンコニニウムブロマイド、N−(3,5−ジメトキシフェニル)メチルシンコニニウムブロマイド、N−(2−エトキシフェニル)メチルシンコニニウムブロマイド、N−(3−エトキシフェニル)メチルシンコニニウムブロマイド、N−(4−エトキシフェニル)メチルシンコニニウムブロマイド、N−(3,5−ジエトキシフェニル)メチルシンコニニウムブロマイド、N−(2−n−プロポキシフェニル)メチルシンコニニウムブロマイド、N−(3−n−プロポキシフェニル)メチルシンコニニウムブロマイド、N−(4−n−プロポキシフェニル)メチルシンコニニウムブロマイド、N−(3,5−ジ−n−プロポキシフェニル)メチルシンコニニウムブロマイド、N−(2−iso−プロポキシフェニル)メチルシンコニニウムブロマイド、N−(3−iso−プロポキシフェニル)メチルシンコニニウムブロマイド、N−(4−iso−プロポキシフェニル)メチルシンコニニウムブロマイド、N−(3,5−ジ−iso−プロポキシフェニル)メチルシンコニニウムブロマイド、N−(2−n−ブトキシフェニル)メチルシンコニニウムブロマイド、N−(3−n−ブトキシフェニル)メチルシンコニニウムブロマイド、N−(4−n−ブトキシフェニル)メチルシンコニニウムブロマイド、N−(3,5−ジ−n−ブトキシフェニル)メチルシンコニニウムブロマイド、N−(2−tert−ブトキシフェニル)メチルシンコニニウムブロマイド、N−(3−tert−ブトキシフェニル)メチルシンコニニウムブロマイド、N−(4−tert−ブトキシフェニル)メチルシンコニニウムブロマイド、N−(3,5−ジ−tert−ブトキシフェニル)メチルシンコニニウムブロマイド、N−[2−(トリフルオロメチル)フェニル]メチルシンコニニウムブロマイド、N−[3−(トリフルオロメチル)フェニル]メチルシンコニニウムブロマイド、N−[4−(トリフルオロメチル)フェニル]メチルシンコニニウムブロマイド、N−[3,5−ビス(トリフルオロメチル)フェニル]メチルシンコニニウムブロマイド、N−[3,5−ビス(1−ナフチル)フェニル]メチルシンコニニウムブロマイド、N−{3,5−ビス[3,5−ビス(トリフルオロメチル)フェニル]フェニル}メチルシンコニニウムブロマイド等を挙げることができ、これらブロマイドイオンがフルロライドイオンまたはクロライドイオンに変換されたもの、キヌクリジン骨格の8−位のエチレニル基がエチル基に変換されたもの、キノリン骨格の6−位の水素原子がメトキシ基に変換されたものキニニウム塩、水酸基をp−トルエンスルホニルアミドカルボニルで保護した誘導体も含まれる。   Specific examples of the chiral phase transfer catalyst represented by the general formula (3) of the present invention include N-benzyl cinchonium bromide, N- (2-methylphenyl) methyl cinchonium bromide, N- (3 -Methylphenyl) methyl cinchonium bromide, N- (4-methylphenyl) methyl cinchonium bromide, N- (3,5-dimethylphenyl) methyl cinchonium bromide, N- (2-ethylphenyl) methyl cincho Ninium bromide, N- (3-ethylphenyl) methyl cinchonium bromide, N- (4-ethylphenyl) methyl cinchonium bromide, N- (3,5-diethylphenyl) methyl cinchonium bromide, N- (2-n-propylphenyl) methylcinchoninium bromide, N- (3- -Propylphenyl) methyl cinchonium bromide, N- (4-n-propylphenyl) methyl cinchonium bromide, N- (3,5-di-n-propylphenyl) methyl cinchonium bromide, N- (2 -Iso-propylphenyl) methyl cinchonium bromide, N- (3-iso-propylphenyl) methyl cinchonium bromide, N- (4-iso-propylphenyl) methyl cinchoninium bromide, N- (3,5 -Di-iso-propylphenyl) methyl cinchonium bromide, N- (2-n-butylphenyl) methyl cinchonium bromide, N- (3-n-butylphenyl) methyl cinchonium bromide, N- (4 -N-butylphenyl) methylcinchonium bromide, N- (3 -Di-n-butylphenyl) methyl cinchonium bromide, N- (2-tert-butylphenyl) methyl cinchonium bromide, N- (3-tert-butylphenyl) methyl cinchonium bromide, N- (4 -Tert-butylphenyl) methyl cinchonium bromide, N- (3,5-di-tert-butylphenyl) methyl cinchonium bromide, N- (2-methoxyphenyl) methyl cinchonium bromide, N- (3 -Methoxyphenyl) methyl cinchonium bromide, N- (4-methoxyphenyl) methyl cinchonium bromide, N- (3,5-dimethoxyphenyl) methyl cinchonium bromide, N- (2-ethoxyphenyl) methyl cincho Ninium bromide, N- (3-ethoxyphene Nyl) methyl cinchonium bromide, N- (4-ethoxyphenyl) methyl cinchonium bromide, N- (3,5-diethoxyphenyl) methyl cinchonium bromide, N- (2-n-propoxyphenyl) methyl Cinchonium bromide, N- (3-n-propoxyphenyl) methyl cinchonium bromide, N- (4-n-propoxyphenyl) methyl cinchonium bromide, N- (3,5-di-n-propoxyphenyl) ) Methyl cinchonium bromide, N- (2-iso-propoxyphenyl) methyl cinchoninium bromide, N- (3-iso-propoxyphenyl) methyl cinchonium bromide, N- (4-iso-propoxyphenyl) methyl Cinchonium bromide, N- (3,5-di-i o-propoxyphenyl) methyl cinchonium bromide, N- (2-n-butoxyphenyl) methyl cinchonium bromide, N- (3-n-butoxyphenyl) methyl cinchonium bromide, N- (4-n- Butoxyphenyl) methyl cinchonium bromide, N- (3,5-di-n-butoxyphenyl) methyl cinchonium bromide, N- (2-tert-butoxyphenyl) methyl cinchonium bromide, N- (3- tert-butoxyphenyl) methylcinchonium bromide, N- (4-tert-butoxyphenyl) methylcinchoninium bromide, N- (3,5-di-tert-butoxyphenyl) methylcinchoninium bromide, N- [ 2- (trifluoromethyl) phenyl] methylcinchoni Um bromide, N- [3- (trifluoromethyl) phenyl] methylcinchonium bromide, N- [4- (trifluoromethyl) phenyl] methyl cinchonium bromide, N- [3,5-bis (trifluoro) Methyl) phenyl] methylcinchoninium bromide, N- [3,5-bis (1-naphthyl) phenyl] methylcinchoninium bromide, N- {3,5-bis [3,5-bis (trifluoromethyl) Phenyl] phenyl} methyl cinchonium bromide, etc., and those in which these bromide ions are converted to fluoride ions or chloride ions, and those in which the 8-position ethylenyl group of the quinuclidine skeleton is converted to an ethyl group A quininium salt in which the 6-position hydrogen atom of the quinoline skeleton is converted to a methoxy group Also included are derivatives in which the hydroxyl group is protected with p-toluenesulfonylamidocarbonyl.

本発明の一般式(1)で表される3−オキソピラゾリジン誘導体の製造において、一般式(3)で表わされるキラル相間移動触媒の使用量は、反応に具するN,N−ベタイン誘導体に対して、0.005〜0.5モルの範囲で使用可能で、反応条件等により、適切な量を使用する。   In the production of the 3-oxopyrazolidine derivative represented by the general formula (1) of the present invention, the amount of the chiral phase transfer catalyst represented by the general formula (3) is the N, N-betaine derivative included in the reaction. Can be used in the range of 0.005 to 0.5 mol, and an appropriate amount is used depending on the reaction conditions and the like.

本発明の一般式(1)で表される3−オキソピラゾリジン誘導体の製造において、使用するトリメチルシリルトリフルオロメタンの使用量は、反応に具するN,N−ベタイン誘導体に対して等モル量以上であれば良いが、反応を円滑に進行させるために1.5〜15モル量使用することが好ましい。   In the production of the 3-oxopyrazolidine derivative represented by the general formula (1) of the present invention, the amount of trimethylsilyl trifluoromethane used is an equimolar amount or more with respect to the N, N-betaine derivative included in the reaction. However, it is preferably used in an amount of 1.5 to 15 moles so that the reaction proceeds smoothly.

本発明の一般式(1)で表される3−オキソピラゾリジン誘導体の製造において適用可能な塩基としては、特に規定はないが、具体的には例えば、水酸化リチウム、水酸化ナトリウム、水酸化カリウム、水酸化セシウム、リチオムメトキシド、リチウムエトキシド、リチウム−iso−プロポキシド、リチウム−tert−ブトキシド、ナトリウムメトキシド、ナトリウムエトキシド、ナトリウム−iso−プロポキシド、ナトリウム−tert−ブトキシド、カリウムメトキシド、カリウムエトキシド、カリウム−iso−プロポキシド、カリウム−tert−ブトキシド、セシウムメトキシド、セシウムエトキシド、セシウム−iso−プロポキシド、セシウム−tert−ブトキシド、酢酸リチウム、酢酸ナトリウム、酢酸カリウム、酢酸セシウム、フッ化ナトリウム、フッ化カリウム、フッ化セシウム、炭酸リチウム、炭酸ナトリウム、炭酸カリウム、炭酸セシウム、ナトリウムフェノキシド、カリウムフェノキシド、テトラメチルアンモニウムフルオリド、テトラ−n−ブチルアノモニウムフルオリド、テトラ−n−ブチルアンモニム−トリフェニルスズジフルオリド等が挙げられ、反応に具するN,N−ベタイン誘導体に対して0.02〜10モル量使用する。   The base applicable in the production of the 3-oxopyrazolidine derivative represented by the general formula (1) of the present invention is not particularly limited. Specifically, for example, lithium hydroxide, sodium hydroxide, water Potassium oxide, cesium hydroxide, lithiome methoxide, lithium ethoxide, lithium-iso-propoxide, lithium-tert-butoxide, sodium methoxide, sodium ethoxide, sodium-iso-propoxide, sodium-tert-butoxide, Potassium methoxide, potassium ethoxide, potassium-iso-propoxide, potassium-tert-butoxide, cesium methoxide, cesium ethoxide, cesium-iso-propoxide, cesium-tert-butoxide, lithium acetate, sodium acetate, potassium acetate , Cesium acid, sodium fluoride, potassium fluoride, cesium fluoride, lithium carbonate, sodium carbonate, potassium carbonate, cesium carbonate, sodium phenoxide, potassium phenoxide, tetramethylammonium fluoride, tetra-n-butylanonium fluoride, tetra -N-butylammonium-triphenyltin difluoride etc. are mentioned, and 0.02-10 mol amount is used with respect to the N, N-betaine derivative | guide_body provided for reaction.

本発明の一般式(1)で表される3−オキソピラゾリジン誘導体の製造において、適用可能な溶剤としては、反応に不活性なものであれば、特に規定はないが、具体的には例えば、ジエチルエーテル、テトラヒドロフラン等のエーテル類、ジクロロメタン、クロロホルム、1,2−ジクロロエタン等のハロゲン化炭化水素類、ベンゼン、トルエン、エチルベンゼン、キシレン等の芳香族炭化水素類が挙げられ、各々単独で用いても良いし、必要に応じて混合して用いても良い。溶剤の使用量としては、反応に具する基質に対して、通常1重量倍〜200重量倍量の範囲で使用可能である。   In the production of the 3-oxopyrazolidine derivative represented by the general formula (1) of the present invention, the applicable solvent is not particularly limited as long as it is inert to the reaction. Examples include ethers such as diethyl ether and tetrahydrofuran, halogenated hydrocarbons such as dichloromethane, chloroform, and 1,2-dichloroethane, and aromatic hydrocarbons such as benzene, toluene, ethylbenzene, and xylene. Alternatively, they may be mixed and used as necessary. The amount of the solvent used can usually be in the range of 1 to 200 times by weight with respect to the substrate provided for the reaction.

本発明の一般式(1)で表される3−オキソピラゾリジン誘導体の製造において、反応温度及び時間は、用いるN,N−ベタイン誘導体の種類、キラル触媒の種類により異なるが。通常−80〜30℃の温度範囲で、1〜48時間で反応は完結する。
本発明の一般式(4)で表わされる光学活性アミン類として、Rがメチル基、エチル基、炭素数3〜10の直鎖、分岐若しくは環式のアルキル基であるものとしては、具体的に例えば、(S)−1,1,1−トリフルオロ−2−アミノプロパン、(S)−1,1,1−トリフルオロ−2−アミノブタン、(S)−1,1,1−トリフルオロ−2−アミノペンタン、(S)−1,1,1−トリフルオロ−2−アミノ−3−メチルブタン、(S)−1,1,1−トリフルオロ−2−アミノヘプタン、(S)−1,1,1−トリフルオロ−2−アミノ−3,3−ジメチルブタン、(S)−1,1,1−トリフルオロ−2−アミノヘプタン、(S)−1,1,1−トリフルオロ−2−アミノオクタン、(S)−1,1,1−トリフルオロ−2−アミノ−3−シクロヘキシルエタン、(S)−1,1,1−トリフルオロ−2−アミノノナン、(S)−1,1,1−トリフルオロ−2−アミノデカン、(S)−1,1,1−トリフルオロ−2−アミノウンデカン、(S)−1,1,1−トリフルオロ−2−アミノドデカン等を挙げることができる。
In the production of the 3-oxopyrazolidine derivative represented by the general formula (1) of the present invention, the reaction temperature and time vary depending on the type of N, N-betaine derivative used and the type of chiral catalyst. The reaction is usually completed within 1 to 48 hours in the temperature range of -80 to 30 ° C.
Specific examples of the optically active amines represented by the general formula (4) of the present invention include those in which R 3 is a methyl group, an ethyl group, a linear, branched or cyclic alkyl group having 3 to 10 carbon atoms. For example, (S) -1,1,1-trifluoro-2-aminopropane, (S) -1,1,1-trifluoro-2-aminobutane, (S) -1,1,1-trifluoro 2-aminopentane, (S) -1,1,1-trifluoro-2-amino-3-methylbutane, (S) -1,1,1-trifluoro-2-aminoheptane, (S) -1 , 1,1-trifluoro-2-amino-3,3-dimethylbutane, (S) -1,1,1-trifluoro-2-aminoheptane, (S) -1,1,1-trifluoro- 2-aminooctane, (S) -1,1,1-trifluoro-2-amino No-3-cyclohexylethane, (S) -1,1,1-trifluoro-2-aminononane, (S) -1,1,1-trifluoro-2-aminodecane, (S) -1,1,1 -Trifluoro-2-aminoundecane, (S) -1,1,1-trifluoro-2-aminododecane and the like can be mentioned.

本発明の、前記一般式(4)で表される光学活性アミン類として、Rが置換基を有しても良いフェニル基であるものとしては、具体的には例えば、(S)−2,2,2−トリフルオロ−1−フェニル−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(2−メチルフェニル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(3−メチルフェニル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(4−メチルフェニル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(2−エチルフェニル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(3−エチルフェニル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(4−エチルフェニル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(2−n−プロピルフェニル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(3−n−プロピルフェニル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(4−n−プロピルフェニル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(2−iso−プロピルフェニル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(3−iso−プロピルフェニル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(4−iso−プロピルフェニル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(2−n−ブチルフェニル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(3−n−ブチルフェニル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(4−n−ブチルフェニル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(2−iso−ブチルフェニル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(3−iso−ブチルフェニル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(4−iso−ブチルフェニル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(2−tert−ブチルフェニル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(3−tert−ブチルフェニル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(4−tert−ブチルフェニル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(4−n−ペンチルフェニル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(4−n−ヘキシルフェニル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(4−n−ヘプチルフェニル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(4−n−オクチルフェニル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(4−n−ノニルフェニル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(4−n−デシルフェニル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(2−メトキシフェニル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(3−メトキシフェニル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(4−メトキシフェニル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(2−エトキシフェニル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(3−エトキシフェニル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(4−エトキシフェニル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(2−n−プロポキシフェニル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(3−n−プロポキシフェニル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(4−n−プロポキシフェニル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(2−iso−プロポキシフェニル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(3−iso−プロポキシフェニル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(4−iso−プロポキシフェニル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(2−n−ブトキシフェニル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(3−n−ブトキシフェニル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(4−n−ブトキシフェニル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(2−iso−ブトキシフェニル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(3−iso−ブトキシフェニル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(4−iso−ブトキシフェニル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(2−tert−ブトキシフェニル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(3−tert−ブトキシフェニル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(4−tert−ブトキシフェニル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(4−n−ペントキシフェニル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(4−n−ヘキシルオキシフェニル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(4−n−ヘプチルオキシフェニル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(4−n−オクチルオキシフェニル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(4−n−ノニルオキシフェニル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(4−n−デシルオキシフェニル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(2−フルオロフェニル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(3−フルオロフェニル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(4−フルオロフェニル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(2−クロロフェニル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(3−クロロフェニル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(4−クロロフェニル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(2−ブロモフェニル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(3−ブロモフェニル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(4−ブロモフェニル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(2−シアノフェニル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(3−シアノフェニル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(4−シアノフェニル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(2−ニトロフェニル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(3−ニトロフェニル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(4−ニトロフェニル)−1−アミノエタン等を挙げることができる。 Specific examples of the optically active amines represented by the general formula (4) of the present invention in which R 3 is a phenyl group which may have a substituent include (S) -2. , 2,2-trifluoro-1-phenyl-1-aminoethane, (S) -2,2,2-trifluoro-1- (2-methylphenyl) -1-aminoethane, (S) -2,2, 2-trifluoro-1- (3-methylphenyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (4-methylphenyl) -1-aminoethane, (S) -2, 2,2-trifluoro-1- (2-ethylphenyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (3-ethylphenyl) -1-aminoethane, (S)- 2,2,2-trifluoro-1- (4-ethylphenyl) -1- Aminoethane, (S) -2,2,2-trifluoro-1- (2-n-propylphenyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (3-n- Propylphenyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (4-n-propylphenyl) -1-aminoethane, (S) -2,2,2-trifluoro-1 -(2-iso-propylphenyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (3-iso-propylphenyl) -1-aminoethane, (S) -2,2, 2-trifluoro-1- (4-iso-propylphenyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (2-n-butylphenyl) -1-aminoethane, (S ) -2,2,2-trifluoro-1- ( -N-butylphenyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (4-n-butylphenyl) -1-aminoethane, (S) -2,2,2-tri Fluoro-1- (2-iso-butylphenyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (3-iso-butylphenyl) -1-aminoethane, (S) -2 , 2,2-trifluoro-1- (4-iso-butylphenyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (2-tert-butylphenyl) -1-aminoethane (S) -2,2,2-trifluoro-1- (3-tert-butylphenyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (4-tert-butyl) Phenyl) -1-aminoethane, (S -2,2,2-trifluoro-1- (4-n-pentylphenyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (4-n-hexylphenyl) -1 -Aminoethane, (S) -2,2,2-trifluoro-1- (4-n-heptylphenyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (4-n -Octylphenyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (4-n-nonylphenyl) -1-aminoethane, (S) -2,2,2-trifluoro- 1- (4-n-decylphenyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (2-methoxyphenyl) -1-aminoethane, (S) -2,2,2 -Trifluoro-1- (3-methoxyphenyl) -1-aminoeta (S) -2,2,2-trifluoro-1- (4-methoxyphenyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (2-ethoxyphenyl)- 1-aminoethane, (S) -2,2,2-trifluoro-1- (3-ethoxyphenyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (4-ethoxyphenyl) ) -1-aminoethane, (S) -2,2,2-trifluoro-1- (2-n-propoxyphenyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- ( 3-n-propoxyphenyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (4-n-propoxyphenyl) -1-aminoethane, (S) -2,2,2- Trifluoro-1- (2-iso-propoxyphenyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (3-iso-propoxyphenyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (4 -Iso-propoxyphenyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (2-n-butoxyphenyl) -1-aminoethane, (S) -2,2,2-tri Fluoro-1- (3-n-butoxyphenyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (4-n-butoxyphenyl) -1-aminoethane, (S) -2 , 2,2-trifluoro-1- (2-iso-butoxyphenyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (3-iso-butoxyphenyl) -1-aminoethane , (S) -2,2,2-G Fluoro-1- (4-iso-butoxyphenyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (2-tert-butoxyphenyl) -1-aminoethane, (S) -2 , 2,2-trifluoro-1- (3-tert-butoxyphenyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (4-tert-butoxyphenyl) -1-aminoethane (S) -2,2,2-trifluoro-1- (4-n-pentoxyphenyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (4-n- (Hexyloxyphenyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (4-n-heptyloxyphenyl) -1-aminoethane, (S) -2,2,2-trifluoro -1- (4-n-oct Tiloxyphenyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (4-n-nonyloxyphenyl) -1-aminoethane, (S) -2,2,2-trifluoro -1- (4-n-decyloxyphenyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (2-fluorophenyl) -1-aminoethane, (S) -2,2 , 2-trifluoro-1- (3-fluorophenyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (4-fluorophenyl) -1-aminoethane, (S) -2 , 2,2-trifluoro-1- (2-chlorophenyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (3-chlorophenyl) -1-aminoethane, (S) -2 , 2,2-trifluoro-1- ( -Chlorophenyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (2-bromophenyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- ( 3-bromophenyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (4-bromophenyl) -1-aminoethane, (S) -2,2,2-trifluoro-1 -(2-cyanophenyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (3-cyanophenyl) -1-aminoethane, (S) -2,2,2-trifluoro -1- (4-cyanophenyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (2-nitrophenyl) -1-aminoethane, (S) -2,2,2- Trifluoro-1- (3-nitrophenyl) -1- Minoetan, mention may be made of (S) -2,2,2- trifluoro- 1 (4-nitrophenyl) -1-aminoethane, or the like.

本発明の、前記一般式(4)で表される光学活性アミン類として、Rが置換基を有しても良い1−ナフチル基であるものとしては、具体的には例えば、(S)−2,2,2−トリフルオロ−1−(1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(2−メチル−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(3−メチル−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(4−メチル−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(5−メチル−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(6−メチル−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(7−メチル−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(8−メチル−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(2−エチル−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(3−エチル−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(4−エチル−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(5−エチル−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(6−エチル−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(7−エチル−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(8−エチル−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(2−n−プロピル−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(3−n−プロピル−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(4−n−プロピル−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(5−n−プロピル−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(6−n−プロピル−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(7−n−プロピル−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(8−n−プロピル−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(2−iso−プロピル−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(3−iso−プロピル−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(4−iso−プロピル−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(5−iso−プロピル−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(6−iso−プロピル−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(7−iso−プロピル−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(8−iso−プロピル−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(2−n−ブチル−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(3−n−ブチル−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(4−n−ブチル−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(5−n−ブチル−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(6−n−ブチル−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(7−n−ブチル−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(8−n−ブチル−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(2−iso−ブチル−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(3−iso−ブチル−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(4−iso−ブチル−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(5−iso−ブチル−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(6−iso−ブチル−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(7−iso−ブチル−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(8−iso−ブチル−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(2−tert−ブチル−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(3−tert−ブチル−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(4−tert−ブチル−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(5−tert−ブチル−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(6−tert−ブチル−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(7−tert−ブチル−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(8−tert−ブチル−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(2−n−ペンチル−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(4−n−ペンチル−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(6−n−ペンチル−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(8−n−ペンチル−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(2−n−ヘキシル−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(4−n−ヘキシル−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(6−n−ヘキシル−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(8−n−ヘキシル−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(2−n−ヘプチル−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(4−n−ヘプチル−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(6−n−ヘプチル−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(8−n−ヘプチル−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(2−n−オクチル−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(4−n−オクチル−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(6−n−オクチル−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(8−n−オクチル−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(2−n−ノニル−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(4−n−ノニル−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(6−n−ノニル−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(8−n−ノニル−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(2−n−デシル−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(4−n−デシル−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(6−n−デシル−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(8−n−デシル−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(2−メトキシ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(3−メトキシ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(4−メトキシ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(5−メトキシ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(6−メトキシ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(7−メトキシ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(8−メトキシ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(2−エトキシ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(3−エトキシ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(4−エトキシ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(5−エトキシ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(6−エトキシ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(7−エトキシ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(8−エトキシ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(2−n−プロポキシ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(3−n−プロポキシ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(4−n−プロポキシ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(5−n−プロポキシ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(6−n−プロポキシ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(7−n−プロポキシ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(8−n−プロポキシ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(2−iso−プロポキシ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(3−iso−プロポキシ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(4−iso−プロポキシ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(5−iso−プロポキシ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(6−iso−プロポキシ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(7−iso−プロポキシ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(8−iso−プロポキシ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(2−n−ブトキシ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(3−n−ブトキシ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(4−n−ブトキシ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(5−n−ブトキシ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(6−n−ブトキシ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(7−n−ブトキシ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(8−n−ブトキシ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(2−iso−ブトキシ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフル
オロ−1−(3−iso−ブトキシ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(4−iso−ブトキシ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(5−iso−ブトキシ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(6−iso−ブトキシ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(7−iso−ブトキシ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(8−iso−ブトキシ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(2−tert−ブトキシ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(3−tert−ブトキシ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(4−tert−ブトキシ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(5−tert−ブトキシ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(6−tert−ブトキシ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(7−tert−ブトキシ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(8−tert−ブトキシ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(2−n−ペントキシ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(4−n−ペントキシ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(6−n−ペントキシ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(8−n−ペントキシ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(2−n−ヘキシルオキシ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(4−n−ヘキシルオキシ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(6−n−ヘキシルオキシ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(8−n−ヘキシルオキシ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(2−n−ヘプチルオキシ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(4−n−ヘプチルオキシ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(6−n−ヘプチルオキシ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(8−n−ヘプチルオキシ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(2−n−オクチルオキシ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(4−n−オクチルオキシ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(6−n−オクチルオキシ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(8−n−オクチルオキシ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(2−n−ノニルオキシ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(4−n−ノニルオキシ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(6−n−ノニルオキシ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(8−n−ノニルオキシ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(2−n−デシルオキシ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(4−n−デシルオキシ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(6−n−デシルオキシ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(8−n−デシルオキシ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(2−フルオロ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(3−フルオロ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(4−フルオロ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(5−フルオロ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(6−フルオロ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(7−フルオロ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(8−フルオロ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(2−クロロ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(3−クロロ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(4−クロロ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(5−クロロ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(6−クロロ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(7−クロロ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(8−クロロ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(2−ブロモ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(3−ブロモ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(4−ブロモ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(5−ブロモ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(6−ブロモ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(7−ブロモ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(8−ブロモ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(2−シアノ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(3−シアノ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(4−シアノ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(5−シアノ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(6−シアノ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(7−シアノ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(8−シアノ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(2−ニトロ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(3−ニトロ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(4−ニトロ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(5−ニトロ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(6−ニトロ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(7−ニトロ−1−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(8−ニトロ−1−ナフチル)−1−アミノエタン等を挙げることができる。
Specific examples of the optically active amines represented by the general formula (4) of the present invention wherein R 3 is a 1-naphthyl group optionally having a substituent include, for example, (S) -2,2,2-trifluoro-1- (1-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (2-methyl-1-naphthyl) -1-aminoethane (S) -2,2,2-trifluoro-1- (3-methyl-1-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (4-methyl- 1-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (5-methyl-1-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro -1- (6-methyl-1-naphthyl) -1-aminoethane, (S) -2,2,2-tri Fluoro-1- (7-methyl-1-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (8-methyl-1-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (2-ethyl-1-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (3-ethyl-1-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (4-ethyl-1-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- ( 5-ethyl-1-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (6-ethyl-1-naphthyl) -1-aminoethane, (S) -2,2, 2-trifluoro-1- (7-ethyl-1-naphthyl) -1-aminoethane, ( ) -2,2,2-trifluoro-1- (8-ethyl-1-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (2-n-propyl-1) -Naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (3-n-propyl-1-naphthyl) -1-aminoethane, (S) -2,2,2-tri Fluoro-1- (4-n-propyl-1-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (5-n-propyl-1-naphthyl) -1-aminoethane (S) -2,2,2-trifluoro-1- (6-n-propyl-1-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (7- n-propyl-1-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro -1- (8-n-propyl-1-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (2-iso-propyl-1-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (3-iso-propyl-1-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (4-iso -Propyl-1-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (5-iso-propyl-1-naphthyl) -1-aminoethane, (S) -2,2 , 2-trifluoro-1- (6-iso-propyl-1-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (7-iso-propyl-1-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro B-1- (8-Iso-propyl-1-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (2-n-butyl-1-naphthyl) -1-aminoethane (S) -2,2,2-trifluoro-1- (3-n-butyl-1-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (4- n-butyl-1-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (5-n-butyl-1-naphthyl) -1-aminoethane, (S) -2, 2,2-trifluoro-1- (6-n-butyl-1-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (7-n-butyl-1-naphthyl) ) -1-Aminoethane, (S) -2,2,2-trifluoro-1- (8-n-butyl-1-) Butyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (2-iso-butyl-1-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro -1- (3-iso-butyl-1-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (4-iso-butyl-1-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (5-iso-butyl-1-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (6-iso -Butyl-1-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (7-iso-butyl-1-naphthyl) -1-aminoethane, (S) -2,2 , 2-Trifluoro-1- (8-iso-butyl-1-naphthyl -1-aminoethane, (S) -2,2,2-trifluoro-1- (2-tert-butyl-1-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1 -(3-tert-butyl-1-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (4-tert-butyl-1-naphthyl) -1-aminoethane, (S ) -2,2,2-trifluoro-1- (5-tert-butyl-1-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (6-tert-butyl) -1-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (7-tert-butyl-1-naphthyl) -1-aminoethane, (S) -2,2,2 -Trifluoro-1- (8-tert-butyl-1-naphth Til) -1-aminoethane, (S) -2,2,2-trifluoro-1- (2-n-pentyl-1-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro -1- (4-n-pentyl-1-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (6-n-pentyl-1-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (8-n-pentyl-1-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (2-n -Hexyl-1-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (4-n-hexyl-1-naphthyl) -1-aminoethane, (S) -2,2 , 2-Trifluoro-1- (6-n-hexyl-1-naphthyl) -1-aminoethane (S) -2,2,2-trifluoro-1- (8-n-hexyl-1-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (2- n-heptyl-1-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (4-n-heptyl-1-naphthyl) -1-aminoethane, (S) -2, 2,2-trifluoro-1- (6-n-heptyl-1-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (8-n-heptyl-1-naphthyl) ) -1-aminoethane, (S) -2,2,2-trifluoro-1- (2-n-octyl-1-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro- 1- (4-n-octyl-1-naphthyl) -1-aminoethane, (S) -2,2,2 Trifluoro-1- (6-n-octyl-1-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (8-n-octyl-1-naphthyl) -1- Aminoethane, (S) -2,2,2-trifluoro-1- (2-n-nonyl-1-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (4 -N-nonyl-1-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (6-n-nonyl-1-naphthyl) -1-aminoethane, (S) -2 , 2,2-trifluoro-1- (8-n-nonyl-1-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (2-n-decyl-1- Naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (4-n-deci Ru-1-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (6-n-decyl-1-naphthyl) -1-aminoethane, (S) -2,2, 2-trifluoro-1- (8-n-decyl-1-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (2-methoxy-1-naphthyl) -1- Aminoethane, (S) -2,2,2-trifluoro-1- (3-methoxy-1-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (4-methoxy -1-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (5-methoxy-1-naphthyl) -1-aminoethane, (S) -2,2,2-tri Fluoro-1- (6-methoxy-1-naphthyl) -1-aminoethane, (S)- , 2,2-trifluoro-1- (7-methoxy-1-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (8-methoxy-1-naphthyl) -1 -Aminoethane, (S) -2,2,2-trifluoro-1- (2-ethoxy-1-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (3- Ethoxy-1-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (4-ethoxy-1-naphthyl) -1-aminoethane, (S) -2,2,2- Trifluoro-1- (5-ethoxy-1-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (6-ethoxy-1-naphthyl) -1-aminoethane, (S ) -2,2,2-trifluoro-1- (7-ethoxy-1- Butyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (8-ethoxy-1-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1 -(2-n-propoxy-1-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (3-n-propoxy-1-naphthyl) -1-aminoethane, (S ) -2,2,2-trifluoro-1- (4-n-propoxy-1-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (5-n-propoxy) -1-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (6-n-propoxy-1-naphthyl) -1-aminoethane, (S) -2,2,2 -Trifluoro-1- (7-n-propoxy-1-naphthyl) -1- Aminoethane, (S) -2,2,2-trifluoro-1- (8-n-propoxy-1-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (2 -Iso-propoxy-1-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (3-iso-propoxy-1-naphthyl) -1-aminoethane, (S) -2 , 2,2-trifluoro-1- (4-iso-propoxy-1-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (5-iso-propoxy-1- Naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (6-iso-propoxy-1-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro -1- (7-iso-propoxy-1- Butyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (8-iso-propoxy-1-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro -1- (2-n-butoxy-1-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (3-n-butoxy-1-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (4-n-butoxy-1-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (5-n -Butoxy-1-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (6-n-butoxy-1-naphthyl) -1-aminoethane, (S) -2,2 , 2-Trifluoro-1- (7-n-butoxy-1-naphthyl) -1- Minoethane, (S) -2,2,2-trifluoro-1- (8-n-butoxy-1-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (2 -Iso-butoxy-1-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (3-iso-butoxy-1-naphthyl) -1-aminoethane, (S) -2 , 2,2-trifluoro-1- (4-iso-butoxy-1-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (5-iso-butoxy-1- Naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (6-iso-butoxy-1-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro -1- (7-iso-butoxy-1-naphthyl) -1- Aminoethane, (S) -2,2,2-trifluoro-1- (8-iso-butoxy-1-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (2 -Tert-butoxy-1-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (3-tert-butoxy-1-naphthyl) -1-aminoethane, (S) -2 , 2,2-trifluoro-1- (4-tert-butoxy-1-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (5-tert-butoxy-1- Naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (6-tert-butoxy-1-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro -1- (7-tert-butoxy-1 Naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (8-tert-butoxy-1-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro -1- (2-n-pentoxy-1-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (4-n-pentoxy-1-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (6-n-pentoxy-1-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (8-n -Pentoxy-1-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (2-n-hexyloxy-1-naphthyl) -1-aminoethane, (S) -2, 2,2-trifluoro-1- (4-n-hexyloxy 1-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (6-n-hexyloxy-1-naphthyl) -1-aminoethane, (S) -2,2,2 -Trifluoro-1- (8-n-hexyloxy-1-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (2-n-heptyloxy-1-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (4-n-heptyloxy-1-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro- 1- (6-n-heptyloxy-1-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (8-n-heptyloxy-1-naphthyl) -1-aminoethane , (S) -2,2,2-trifluoro-1- (2- n-octyloxy-1-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (4-n-octyloxy-1-naphthyl) -1-aminoethane, (S)- 2,2,2-trifluoro-1- (6-n-octyloxy-1-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (8-n-octyloxy) -1-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (2-n-nonyloxy-1-naphthyl) -1-aminoethane, (S) -2,2,2 -Trifluoro-1- (4-n-nonyloxy-1-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (6-n-nonyloxy-1-naphthyl) -1 -Aminoethane, (S) -2,2,2-trifluoro -1- (8-n-nonyloxy-1-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (2-n-decyloxy-1-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (4-n-decyloxy-1-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (6-n -Decyloxy-1-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (8-n-decyloxy-1-naphthyl) -1-aminoethane, (S) -2,2 , 2-trifluoro-1- (2-fluoro-1-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (3-fluoro-1-naphthyl) -1-aminoethane , (S) -2,2,2-trifluoro-1- ( -Fluoro-1-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (5-fluoro-1-naphthyl) -1-aminoethane, (S) -2,2,2 -Trifluoro-1- (6-fluoro-1-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (7-fluoro-1-naphthyl) -1-aminoethane, S) -2,2,2-trifluoro-1- (8-fluoro-1-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (2-chloro-1- Naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (3-chloro-1-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1 -(4-Chloro-1-naphthyl) -1-aminoethane, (S) -2 , 2,2-trifluoro-1- (5-chloro-1-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (6-chloro-1-naphthyl) -1 -Aminoethane, (S) -2,2,2-trifluoro-1- (7-chloro-1-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (8- Chloro-1-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (2-bromo-1-naphthyl) -1-aminoethane, (S) -2,2,2- Trifluoro-1- (3-bromo-1-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (4-bromo-1-naphthyl) -1-aminoethane, (S ) -2,2,2-trifluoro-1- (5-bromo-1-naphthyl) -1-a Noethane, (S) -2,2,2-trifluoro-1- (6-bromo-1-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (7-bromo) -1-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (8-bromo-1-naphthyl) -1-aminoethane, (S) -2,2,2-tri Fluoro-1- (2-cyano-1-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (3-cyano-1-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (4-cyano-1-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (5-cyano-1-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (6-cyano- -Naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (7-cyano-1-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro- 1- (8-cyano-1-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (2-nitro-1-naphthyl) -1-aminoethane, (S) -2 , 2,2-trifluoro-1- (3-nitro-1-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (4-nitro-1-naphthyl) -1 -Aminoethane, (S) -2,2,2-trifluoro-1- (5-nitro-1-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (6- Nitro-1-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro Examples include -1- (7-nitro-1-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (8-nitro-1-naphthyl) -1-aminoethane, and the like. it can.

本発明の、前記一般式(4)で表される光学活性アミン類として、Rが置換基を有しても良い2−ナフチル基であるものとしては、具体的には例えば、(S)−2,2,2−トリフルオロ−1−(2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(1−メチル−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(3−メチル−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(4−メチル−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(5−メチル−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(6−メチル−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(7−メチル−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(8−メチル−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(1−エチル−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(3−エチル−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(4−エチル−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(5−エチル−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(6−エチル−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(7−エチル−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(8−エチル−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(1−n−プロピル−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(3−n−プロピル−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(4−n−プロピル−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(5−n−プロピル−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(6−n−プロピル−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(7−n−プロピル−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(8−n−プロピル−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(1−iso−プロピル−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(3−iso−プロピル−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(4−iso−プロピル−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(5−iso−プロピル−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(6−iso−プロピル−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(7−iso−プロピル−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(8−iso−プロピル−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(1−n−ブチル−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(3−n−ブチル−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(4−n−ブチル−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(5−n−ブチル−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(6−n−ブチル−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(7−n−ブチル−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(8−n−ブチル−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(1−iso−ブチル−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(3−iso−ブチル−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(4−iso−ブチル−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(5−iso−ブチル−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(6−iso−ブチル−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(7−iso−ブチル−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(8−iso−ブチル−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(1−tert−ブチル−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(3−tert−ブチル−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(4−tert−ブチル−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(5−tert−ブチル−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(6−tert−ブチル−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(7−tert−ブチル−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(8−tert−ブチル−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(1−n−ペンチル−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(4−n−ペンチル−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(6−n−ペンチル−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(8−n−ペンチル−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(1−n−ヘキシル−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(4−n−ヘキシル−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(6−n−ヘキシル−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(8−n−ヘキシル−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(1−n−ヘプチル−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(4−n−ヘプチル−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(6−n−ヘプチル−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(8−n−ヘプチル−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(1−n−オクチル−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(4−n−オクチル−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(6−n−オクチル−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(8−n−オクチル−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(1−n−ノニル−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(4−n−ノニル−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(6−n−ノニル−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(8−n−ノニル−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(1−n−デシル−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(4−n−デシル−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(6−n−デシル−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(8−n−デシル−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(1−メトキシ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(3−メトキシ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(4−メトキシ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(5−メトキシ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(6−メトキシ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(7−メトキシ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(8−メトキシ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(1−エトキシ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(3−エトキシ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(4−エトキシ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(5−エトキシ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(6−エトキシ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(7−エトキシ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(8−エトキシ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(1−n−プロポキシ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(3−n−プロポキシ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(4−n−プロポキシ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(5−n−プロポキシ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(6−n−プロポキシ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(7−n−プロポキシ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(8−n−プロポキシ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(1−iso−プロポキシ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(3−iso−プロポキシ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(4−iso−プロポキシ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(5−iso−プロポキシ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(6−iso−プロポキシ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(7−iso−プロポキシ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(8−iso−プロポキシ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(1−n−ブトキシ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(3−n−ブトキシ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(4−n−ブトキシ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(5−n−ブトキシ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(6−n−ブトキシ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(7−n−ブトキシ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(8−n−ブトキシ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(1−iso−ブトキシ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフル
オロ−1−(3−iso−ブトキシ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(4−iso−ブトキシ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(5−iso−ブトキシ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(6−iso−ブトキシ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(7−iso−ブトキシ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(8−iso−ブトキシ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(1−tert−ブトキシ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(3−tert−ブトキシ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(4−tert−ブトキシ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(5−tert−ブトキシ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(6−tert−ブトキシ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(7−tert−ブトキシ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(8−tert−ブトキシ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(1−n−ペントキシ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(4−n−ペントキシ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(6−n−ペントキシ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(8−n−ペントキシ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(1−n−ヘキシルオキシ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(4−n−ヘキシルオキシ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(6−n−ヘキシルオキシ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(8−n−ヘキシルオキシ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(1−n−ヘプチルオキシ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(4−n−ヘプチルオキシ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(6−n−ヘプチルオキシ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(8−n−ヘプチルオキシ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(1−n−オクチルオキシ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(4−n−オクチルオキシ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(6−n−オクチルオキシ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(8−n−オクチルオキシ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(1−n−ノニルオキシ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(4−n−ノニルオキシ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(6−n−ノニルオキシ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(8−n−ノニルオキシ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(1−n−デシルオキシ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(4−n−デシルオキシ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(6−n−デシルオキシ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(8−n−デシルオキシ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(1−フルオロ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(3−フルオロ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(4−フルオロ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(5−フルオロ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(6−フルオロ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(7−フルオロ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(8−フルオロ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(1−クロロ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(3−クロロ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(4−クロロ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(5−クロロ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(6−クロロ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(7−クロロ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(8−クロロ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(1−ブロモ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(3−ブロモ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(4−ブロモ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(5−ブロモ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(6−ブロモ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(7−ブロモ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(8−ブロモ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(1−シアノ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(3−シアノ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(4−シアノ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(5−シアノ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(6−シアノ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(7−シアノ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(8−シアノ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(1−ニトロ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(3−ニトロ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(4−ニトロ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(5−ニトロ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(6−ニトロ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(7−ニトロ−2−ナフチル)−1−アミノエタン、(S)−2,2,2−トリフルオロ−1−(8−ニトロ−2−ナフチル)−1−アミノエタン等を挙げることができる。
Specific examples of the optically active amines represented by the general formula (4) of the present invention in which R 3 is an optionally substituted 2-naphthyl group include, for example, (S) -2,2,2-trifluoro-1- (2-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (1-methyl-2-naphthyl) -1-aminoethane (S) -2,2,2-trifluoro-1- (3-methyl-2-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (4-methyl- 2-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (5-methyl-2-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro -1- (6-Methyl-2-naphthyl) -1-aminoethane, (S) -2,2,2-tri Fluoro-1- (7-methyl-2-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (8-methyl-2-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (1-ethyl-2-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (3-ethyl-2-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (4-ethyl-2-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- ( 5-ethyl-2-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (6-ethyl-2-naphthyl) -1-aminoethane, (S) -2,2, 2-trifluoro-1- (7-ethyl-2-naphthyl) -1-aminoethane, ( ) -2,2,2-trifluoro-1- (8-ethyl-2-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (1-n-propyl-2) -Naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (3-n-propyl-2-naphthyl) -1-aminoethane, (S) -2,2,2-tri Fluoro-1- (4-n-propyl-2-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (5-n-propyl-2-naphthyl) -1-aminoethane (S) -2,2,2-trifluoro-1- (6-n-propyl-2-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (7- n-propyl-2-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro -1- (8-n-propyl-2-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (1-iso-propyl-2-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (3-iso-propyl-2-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (4-iso -Propyl-2-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (5-iso-propyl-2-naphthyl) -1-aminoethane, (S) -2,2 , 2-trifluoro-1- (6-iso-propyl-2-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (7-iso-propyl-2-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro B-1- (8-Iso-propyl-2-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (1-n-butyl-2-naphthyl) -1-aminoethane (S) -2,2,2-trifluoro-1- (3-n-butyl-2-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (4- n-butyl-2-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (5-n-butyl-2-naphthyl) -1-aminoethane, (S) -2, 2,2-trifluoro-1- (6-n-butyl-2-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (7-n-butyl-2-naphthyl) ) -1-Aminoethane, (S) -2,2,2-trifluoro-1- (8-n-butyl-2-) Butyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (1-iso-butyl-2-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro -1- (3-iso-butyl-2-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (4-iso-butyl-2-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (5-iso-butyl-2-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (6-iso -Butyl-2-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (7-iso-butyl-2-naphthyl) -1-aminoethane, (S) -2,2 , 2-Trifluoro-1- (8-iso-butyl-2-naphthyl -1-aminoethane, (S) -2,2,2-trifluoro-1- (1-tert-butyl-2-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1 -(3-tert-butyl-2-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (4-tert-butyl-2-naphthyl) -1-aminoethane, (S ) -2,2,2-trifluoro-1- (5-tert-butyl-2-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (6-tert-butyl) -2-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (7-tert-butyl-2-naphthyl) -1-aminoethane, (S) -2,2,2 -Trifluoro-1- (8-tert-butyl-2-naphth Til) -1-aminoethane, (S) -2,2,2-trifluoro-1- (1-n-pentyl-2-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro -1- (4-n-pentyl-2-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (6-n-pentyl-2-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (8-n-pentyl-2-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (1-n -Hexyl-2-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (4-n-hexyl-2-naphthyl) -1-aminoethane, (S) -2,2 , 2-Trifluoro-1- (6-n-hexyl-2-naphthyl) -1-aminoethane (S) -2,2,2-trifluoro-1- (8-n-hexyl-2-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (1- n-heptyl-2-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (4-n-heptyl-2-naphthyl) -1-aminoethane, (S) -2, 2,2-trifluoro-1- (6-n-heptyl-2-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (8-n-heptyl-2-naphthyl) ) -1-aminoethane, (S) -2,2,2-trifluoro-1- (1-n-octyl-2-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro- 1- (4-n-octyl-2-naphthyl) -1-aminoethane, (S) -2,2,2 Trifluoro-1- (6-n-octyl-2-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (8-n-octyl-2-naphthyl) -1- Aminoethane, (S) -2,2,2-trifluoro-1- (1-n-nonyl-2-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (4 -N-nonyl-2-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (6-n-nonyl-2-naphthyl) -1-aminoethane, (S) -2 , 2,2-trifluoro-1- (8-n-nonyl-2-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (1-n-decyl-2- Naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (4-n-deci Ru-2-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (6-n-decyl-2-naphthyl) -1-aminoethane, (S) -2,2, 2-trifluoro-1- (8-n-decyl-2-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (1-methoxy-2-naphthyl) -1- Aminoethane, (S) -2,2,2-trifluoro-1- (3-methoxy-2-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (4-methoxy -2-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (5-methoxy-2-naphthyl) -1-aminoethane, (S) -2,2,2-tri Fluoro-1- (6-methoxy-2-naphthyl) -1-aminoethane, (S)- , 2,2-trifluoro-1- (7-methoxy-2-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (8-methoxy-2-naphthyl) -1 -Aminoethane, (S) -2,2,2-trifluoro-1- (1-ethoxy-2-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (3- Ethoxy-2-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (4-ethoxy-2-naphthyl) -1-aminoethane, (S) -2,2,2- Trifluoro-1- (5-ethoxy-2-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (6-ethoxy-2-naphthyl) -1-aminoethane, (S ) -2,2,2-trifluoro-1- (7-ethoxy-2- Butyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (8-ethoxy-2-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1 -(1-n-propoxy-2-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (3-n-propoxy-2-naphthyl) -1-aminoethane, (S ) -2,2,2-trifluoro-1- (4-n-propoxy-2-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (5-n-propoxy) -2-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (6-n-propoxy-2-naphthyl) -1-aminoethane, (S) -2,2,2 -Trifluoro-1- (7-n-propoxy-2-naphthyl) -1- Aminoethane, (S) -2,2,2-trifluoro-1- (8-n-propoxy-2-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (1 -Iso-propoxy-2-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (3-iso-propoxy-2-naphthyl) -1-aminoethane, (S) -2 , 2,2-trifluoro-1- (4-iso-propoxy-2-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (5-iso-propoxy-2- Naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (6-iso-propoxy-2-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro -1- (7-iso-propoxy-2- Butyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (8-iso-propoxy-2-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro -1- (1-n-butoxy-2-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (3-n-butoxy-2-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (4-n-butoxy-2-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (5-n -Butoxy-2-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (6-n-butoxy-2-naphthyl) -1-aminoethane, (S) -2,2 , 2-Trifluoro-1- (7-n-butoxy-2-naphthyl) -1- Minoethane, (S) -2,2,2-trifluoro-1- (8-n-butoxy-2-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (1 -Iso-butoxy-2-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (3-iso-butoxy-2-naphthyl) -1-aminoethane, (S) -2 , 2,2-trifluoro-1- (4-iso-butoxy-2-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (5-iso-butoxy-2- Naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (6-iso-butoxy-2-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro -1- (7-iso-butoxy-2-naphthyl) -1- Aminoethane, (S) -2,2,2-trifluoro-1- (8-iso-butoxy-2-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (1 -Tert-butoxy-2-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (3-tert-butoxy-2-naphthyl) -1-aminoethane, (S) -2 , 2,2-trifluoro-1- (4-tert-butoxy-2-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (5-tert-butoxy-2- Naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (6-tert-butoxy-2-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro -1- (7-tert-butoxy-2 Naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (8-tert-butoxy-2-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro -1- (1-n-pentoxy-2-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (4-n-pentoxy-2-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (6-n-pentoxy-2-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (8-n -Pentoxy-2-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (1-n-hexyloxy-2-naphthyl) -1-aminoethane, (S) -2, 2,2-trifluoro-1- (4-n-hexyloxy 2-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (6-n-hexyloxy-2-naphthyl) -1-aminoethane, (S) -2,2,2 -Trifluoro-1- (8-n-hexyloxy-2-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (1-n-heptyloxy-2-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (4-n-heptyloxy-2-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro- 1- (6-n-heptyloxy-2-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (8-n-heptyloxy-2-naphthyl) -1-aminoethane , (S) -2,2,2-trifluoro-1- (1- n-octyloxy-2-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (4-n-octyloxy-2-naphthyl) -1-aminoethane, (S)- 2,2,2-trifluoro-1- (6-n-octyloxy-2-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (8-n-octyloxy) -2-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (1-n-nonyloxy-2-naphthyl) -1-aminoethane, (S) -2,2,2 -Trifluoro-1- (4-n-nonyloxy-2-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (6-n-nonyloxy-2-naphthyl) -1 -Aminoethane, (S) -2,2,2-trifluoro -1- (8-n-nonyloxy-2-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (1-n-decyloxy-2-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (4-n-decyloxy-2-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (6-n -Decyloxy-2-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (8-n-decyloxy-2-naphthyl) -1-aminoethane, (S) -2,2 , 2-trifluoro-1- (1-fluoro-2-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (3-fluoro-2-naphthyl) -1-aminoethane , (S) -2,2,2-trifluoro-1- ( -Fluoro-2-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (5-fluoro-2-naphthyl) -1-aminoethane, (S) -2,2,2 -Trifluoro-1- (6-fluoro-2-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (7-fluoro-2-naphthyl) -1-aminoethane, S) -2,2,2-trifluoro-1- (8-fluoro-2-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (1-chloro-2- Naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (3-chloro-2-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1 -(4-Chloro-2-naphthyl) -1-aminoethane, (S) -2 , 2,2-trifluoro-1- (5-chloro-2-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (6-chloro-2-naphthyl) -1 -Aminoethane, (S) -2,2,2-trifluoro-1- (7-chloro-2-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (8- Chloro-2-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (1-bromo-2-naphthyl) -1-aminoethane, (S) -2,2,2- Trifluoro-1- (3-bromo-2-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (4-bromo-2-naphthyl) -1-aminoethane, (S ) -2,2,2-trifluoro-1- (5-bromo-2-naphthyl) -1-a Noethane, (S) -2,2,2-trifluoro-1- (6-bromo-2-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (7-bromo) -2-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (8-bromo-2-naphthyl) -1-aminoethane, (S) -2,2,2-tri Fluoro-1- (1-cyano-2-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (3-cyano-2-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (4-cyano-2-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (5-cyano-2-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (6-cyano- -Naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (7-cyano-2-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro- 1- (8-cyano-2-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (1-nitro-2-naphthyl) -1-aminoethane, (S) -2 , 2,2-trifluoro-1- (3-nitro-2-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (4-nitro-2-naphthyl) -1 -Aminoethane, (S) -2,2,2-trifluoro-1- (5-nitro-2-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (6- Nitro-2-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro -1- (7-nitro-2-naphthyl) -1-aminoethane, (S) -2,2,2-trifluoro-1- (8-nitro-2-naphthyl) -1-aminoethane, and the like. it can.

本発明の、前記一般式(4)で表される光学活性アミン類として、Rが置換基を有しても良いアリールエチレニル基であるものとしては、具体的には例えば、(S)−1−(トリフルオロメチル)−3−フェニル−1−アミノ−2−プロペン、(S)−1−(トリフルオロメチル)−3−(2−メチルフェニル)−1−アミノ−2−プロペン、(S)−1−(トリフルオロメチル)−3−(3−メチルフェニル)−1−アミノ−2−プロペン、(S)−1−(トリフルオロメチル)−3−(4−メチルフェニル)−1−アミノ−2−プロペン、(S)−1−(トリフルオロメチル)−3−(2−エチルフェニル)−1−アミノ−2−プロペン、(S)−1−(トリフルオロメチル)−3−(3−エチルフェニル)−1−アミノ−2−プロペン、(S)−1−(トリフルオロメチル)−3−(4−エチルフェニル)−1−アミノ−2−プロペン、(S)−1−(トリフルオロメチル)−3−(2−n−プロピルフェニル)−1−アミノ−2−プロペン、(S)−1−(トリフルオロメチル)−3−(3−n−プロピルフェニル)−1−アミノ−2−プロペン、(S)−1−(トリフルオロメチル)−3−(4−n−プロピルフェニル)−1−アミノ−2−プロペン、(S)−1−(トリフルオロメチル)−3−(2−iso−プロピルフェニル)−1−アミノ−2−プロペン、(S)−1−(トリフルオロメチル)−3−(3−iso−プロピルフェニル)−1−アミノ−2−プロペン、(S)−1−(トリフルオロメチル)−3−(4−iso−プロピルフェニル)−1−アミノ−2−プロペン、(S)−1−(トリフルオロメチル)−3−(2−n−ブチルフェニル)−1−アミノ−2−プロペン、(S)−1−(トリフルオロメチル)−3−(3−n−ブチルフェニル)−1−アミノ−2−プロペン、(S)−1−(トリフルオロメチル)−3−(4−n−ブチルフェニル)−1−アミノ−2−プロペン、(S)−1−(トリフルオロメチル)−3−(2−sec−ブチルフェニル)−1−アミノ−2−プロペン、(S)−1−(トリフルオロメチル)−3−(3−sec−ブチルフェニル)−1−アミノ−2−プロペン、(S)−1−(トリフルオロメチル)−3−(4−sec−ブチルフェニル)−1−アミノ−2−プロペン、(S)−1−(トリフルオロメチル)−3−(2−tert−ブチルフェニル)−1−アミノ−2−プロペン、(S)−1−(トリフルオロメチル)−3−(3−tert−ブチルフェニル)−1−アミノ−2−プロペン、(S)−1−(トリフルオロメチル)−3−(4−tert−ブチルフェニル)−1−アミノ−2−プロペン、(S)−1−(トリフルオロメチル)−3−(2−メトキシフェニル)−1−アミノ−2−プロペン、(S)−1−(トリフルオロメチル)−3−(3−メトキシフェニル)−1−アミノ−2−プロペン、(S)−1−(トリフルオロメチル)−3−(4−メトキシフェニル)−1−アミノ−2−プロペン、(S)−1−(トリフルオロメチル)−3−(2−エトキシフェニル)−1−アミノ−2−プロペン、(S)−1−(トリフルオロメチル)−3−(3−エトキシフェニル)−1−アミノ−2−プロペン、(S)−1−(トリフルオロメチル)−3−(4−エトキシフェニル)−1−アミノ−2−プロペン、(S)−1−(トリフルオロメチル)−3−(2−n−プロポキシフェニル)−1−アミノ−2−プロペン、(S)−1−(トリフルオロメチル)−3−(3−n−プロポキシフェニル)−1−アミノ−2−プロペン、(S)−1−(トリフルオロメチル)−3−(4−n−プロポキシフェニル)−1−アミノ−2−プロペン、(S)−1−(トリフルオロメチル)−3−(2−iso−プロポキシフェニル)−1−アミノ−2−プロペン、(S)−1−(トリフルオロメチル)−3−(3−iso−プロポキシフェニル)−1−アミノ−2−プロペン、(S)−1−(トリフルオロメチル)−3−(4−iso−プロポキシフェニル)−1−アミノ−2−プロペン、(S)−1−(トリフルオロメチル)−3−(2−n−ブトキシフェニル)−1−アミノ−2−プロペン、(S)−1−(トリフルオロメチル)−3−(3−n−ブトキシフェニル)−1−アミノ−2−プロペン、(S)−1−(トリフルオロメチル)−3−(4−n−ブトキシフェニル)−1−アミノ−2−プロペン、(S)−1−(トリフルオロメチル)−3−(2−sec−ブトキシフェニル)−1−アミノ−2−プロペン、(S)−1−(トリフルオロメチル)−3−(3−sec−ブトキシフェニル)−1−アミノ−2−プロペン、(S)−1−(トリフルオロメチル)−3−(4−sec−ブトキシフェニル)−1−アミノ−2−プロペン、(S)−1−(トリフルオロメチル)−3−(2−tert−ブトキシフェニル)−1−アミノ−2−プロペン、(S)−1−(トリフルオロメチル)−3−(3−tert−ブトキシフェニル)−1−アミノ−2−プロペン、(S)−1−(トリフルオロメチル)−3−(4−tert−ブトキシフェニル)−1−アミノ−2−プロペン、(S)−1−(トリフルオロメチル)−3−(2−フルオロフェニル)−1−アミノ−2−プロペン、(S)−1−(トリフルオロメチル)−3−(3−フルオロフェニル)−1−アミノ−2−プロペン、(S)−1−(トリフルオロメチル)−3−(4−フルオロフェニル)−1−アミノ−2−プロペン、(S)−1−(トリフルオロメチル)−3−(2−クロロフェニル)−1−アミノ−2−プロペン、(S)−1−(トリフルオロメチル)−3−(3−クロロフェニル)−1−アミノ−2−プロペン、(S)−1−(トリフルオロメチル)−3−(4−クロロフェニル)−1−アミノ−2−プロペン、(S)−1−(トリフルオロメチル)−3−(2−ブロモフェニル)−1−アミノ−2−プロペン、(S)−1−(トリフルオロメチル)−3−(3−ブロモフェニル)−1−アミノ−2−プロペン、(S)−1−(トリフルオロメチル)−3−(4−ブロモフェニル)−1−アミノ−2−プロペン、(S)−1−(トリフルオロメチル)−3−(2−シアノフェニル)−1−アミノ−2−プロペン、(S)−1−(トリフルオロメチル)−3−(3−シアノフェニル)−1−アミノ−2−プロペン、(S)−1−(トリフルオロメチル)−3−(4−シアノフェニル)−1−アミノ−2−プロペン、(S)−1−(トリフルオロメチル)−3−(2−ニトロフェニル)−1−アミノ−2−プロペン、(S)−1−(トリフルオロメチル)−3−(3−ニトロフェニル)−1−アミノ−2−プロペン、(S)−1−(トリフルオロメチル)−3−(4−ニトロフェニル)−1−アミノ−2−プロペン等を挙げることができる。 Specific examples of the optically active amines represented by the general formula (4) of the present invention in which R 3 is an arylethylenyl group which may have a substituent include, for example, (S) -1- (trifluoromethyl) -3-phenyl-1-amino-2-propene, (S) -1- (trifluoromethyl) -3- (2-methylphenyl) -1-amino-2-propene, (S) -1- (trifluoromethyl) -3- (3-methylphenyl) -1-amino-2-propene, (S) -1- (trifluoromethyl) -3- (4-methylphenyl)- 1-amino-2-propene, (S) -1- (trifluoromethyl) -3- (2-ethylphenyl) -1-amino-2-propene, (S) -1- (trifluoromethyl) -3 -(3-Ethylphenyl) -1-amino-2-prope (S) -1- (trifluoromethyl) -3- (4-ethylphenyl) -1-amino-2-propene, (S) -1- (trifluoromethyl) -3- (2-n- Propylphenyl) -1-amino-2-propene, (S) -1- (trifluoromethyl) -3- (3-n-propylphenyl) -1-amino-2-propene, (S) -1- ( (Trifluoromethyl) -3- (4-n-propylphenyl) -1-amino-2-propene, (S) -1- (trifluoromethyl) -3- (2-iso-propylphenyl) -1-amino 2-propene, (S) -1- (trifluoromethyl) -3- (3-iso-propylphenyl) -1-amino-2-propene, (S) -1- (trifluoromethyl) -3- (4-Iso-propylphenyl) -1-amino 2-propene, (S) -1- (trifluoromethyl) -3- (2-n-butylphenyl) -1-amino-2-propene, (S) -1- (trifluoromethyl) -3- ( 3-n-butylphenyl) -1-amino-2-propene, (S) -1- (trifluoromethyl) -3- (4-n-butylphenyl) -1-amino-2-propene, (S) -1- (trifluoromethyl) -3- (2-sec-butylphenyl) -1-amino-2-propene, (S) -1- (trifluoromethyl) -3- (3-sec-butylphenyl) -1-amino-2-propene, (S) -1- (trifluoromethyl) -3- (4-sec-butylphenyl) -1-amino-2-propene, (S) -1- (trifluoromethyl) ) -3- (2-tert-butylphenyl)- -Amino-2-propene, (S) -1- (trifluoromethyl) -3- (3-tert-butylphenyl) -1-amino-2-propene, (S) -1- (trifluoromethyl)- 3- (4-tert-butylphenyl) -1-amino-2-propene, (S) -1- (trifluoromethyl) -3- (2-methoxyphenyl) -1-amino-2-propene, (S ) -1- (trifluoromethyl) -3- (3-methoxyphenyl) -1-amino-2-propene, (S) -1- (trifluoromethyl) -3- (4-methoxyphenyl) -1- Amino-2-propene, (S) -1- (trifluoromethyl) -3- (2-ethoxyphenyl) -1-amino-2-propene, (S) -1- (trifluoromethyl) -3- ( 3-Ethoxyphenyl) -1-amino No-2-propene, (S) -1- (trifluoromethyl) -3- (4-ethoxyphenyl) -1-amino-2-propene, (S) -1- (trifluoromethyl) -3- ( 2-n-propoxyphenyl) -1-amino-2-propene, (S) -1- (trifluoromethyl) -3- (3-n-propoxyphenyl) -1-amino-2-propene, (S) -1- (trifluoromethyl) -3- (4-n-propoxyphenyl) -1-amino-2-propene, (S) -1- (trifluoromethyl) -3- (2-iso-propoxyphenyl) -1-amino-2-propene, (S) -1- (trifluoromethyl) -3- (3-iso-propoxyphenyl) -1-amino-2-propene, (S) -1- (trifluoromethyl) ) -3- (4-Iso-Pro Xylphenyl) -1-amino-2-propene, (S) -1- (trifluoromethyl) -3- (2-n-butoxyphenyl) -1-amino-2-propene, (S) -1- (tri Fluoromethyl) -3- (3-n-butoxyphenyl) -1-amino-2-propene, (S) -1- (trifluoromethyl) -3- (4-n-butoxyphenyl) -1-amino- 2-propene, (S) -1- (trifluoromethyl) -3- (2-sec-butoxyphenyl) -1-amino-2-propene, (S) -1- (trifluoromethyl) -3- ( 3-sec-butoxyphenyl) -1-amino-2-propene, (S) -1- (trifluoromethyl) -3- (4-sec-butoxyphenyl) -1-amino-2-propene, (S) -1- (trifluoromethyl) 3- (2-tert-butoxyphenyl) -1-amino-2-propene, (S) -1- (trifluoromethyl) -3- (3-tert-butoxyphenyl) -1-amino-2-propene, (S) -1- (trifluoromethyl) -3- (4-tert-butoxyphenyl) -1-amino-2-propene, (S) -1- (trifluoromethyl) -3- (2-fluorophenyl) ) -1-Amino-2-propene, (S) -1- (trifluoromethyl) -3- (3-fluorophenyl) -1-amino-2-propene, (S) -1- (trifluoromethyl) -3- (4-fluorophenyl) -1-amino-2-propene, (S) -1- (trifluoromethyl) -3- (2-chlorophenyl) -1-amino-2-propene, (S)- 1- (trifluoromethyl L) -3- (3-chlorophenyl) -1-amino-2-propene, (S) -1- (trifluoromethyl) -3- (4-chlorophenyl) -1-amino-2-propene, (S) -1- (trifluoromethyl) -3- (2-bromophenyl) -1-amino-2-propene, (S) -1- (trifluoromethyl) -3- (3-bromophenyl) -1-amino 2-propene, (S) -1- (trifluoromethyl) -3- (4-bromophenyl) -1-amino-2-propene, (S) -1- (trifluoromethyl) -3- (2 -Cyanophenyl) -1-amino-2-propene, (S) -1- (trifluoromethyl) -3- (3-cyanophenyl) -1-amino-2-propene, (S) -1- (tri Fluoromethyl) -3- (4-cyanophenyl) -1 Amino-2-propene, (S) -1- (trifluoromethyl) -3- (2-nitrophenyl) -1-amino-2-propene, (S) -1- (trifluoromethyl) -3- ( 3-nitrophenyl) -1-amino-2-propene, (S) -1- (trifluoromethyl) -3- (4-nitrophenyl) -1-amino-2-propene, and the like.

本発明の、前記一般式(4)で表される光学活性アミン類として、Rが置換基を有しても良いアリールアルキル基であるものとしては、具体的には例えば、(S)−1−(トリフルオロメチル)−3−(2−ニトロフェニル)−1−アミノ−2−プロペン、(S)−1−(トリフルオロメチル)−3−フェニル−1−アミノプロパン、(S)−1−(トリフルオロメチル)−4−フェニル−1−アミノブタン、(S)−1−(トリフルオロメチル)−5−フェニル−1−アミノペンタン、(S)−1−(トリフルオロメチル)−6−フェニル−1−アミノヘキサン、(S)−1−(トリフルオロメチル)−2−(2−メチルフェニル)−1−アミノエタン、(S)−1−(トリフルオロメチル)−2−(3−メチルフェニル)−1−アミノエタン、(S)−1−(トリフルオロメチル)−2−(4−メチルフェニル)−1−アミノエタン、(S)−1−(トリフルオロメチル)−3−(2−メチルフェニル)−1−アミノプロパン、(S)−1−(トリフルオロメチル)−3−(3−メチルフェニル)−1−アミノプロパン、(S)−1−(トリフルオロメチル)−3−(4−メチルフェニル)−1−アミノプロパン、(S)−1−(トリフルオロメチル)−4−(2−メチルフェニル)−1−アミノブタン、(S)−1−(トリフルオロメチル)−4−(3−メチルフェニル)−1−アミノブタン、(S)−1−(トリフルオロメチル)−4−(4−メチルフェニル)−1−アミノブタン、(S)−1−(トリフルオロメチル)−5−(2−メチルフェニル)−1−アミノペンタン、(S)−1−(トリフルオロメチル)−5−(3−メチルフェニル)−1−アミノペンタン、(S)−1−(トリフルオロメチル)−5−(4−メチルフェニル)−1−アミノペンタン、(S)−1−(トリフルオロメチル)−2−(2−エチルフェニル)−1−アミノエタン、(S)−1−(トリフルオロメチル)−2−(3−エチルフェニル)−1−アミノエタン、(S)−1−(トリフルオロメチル)−2−(4−エチルフェニル)−1−アミノエタン、(S)−1−(トリフルオロメチル)−3−(2−エチルフェニル)−1−アミノプロパン、(S)−1−(トリフルオロメチル)−3−(3−エチルフェニル)−1−アミノプロパン、(S)−1−(トリフルオロメチル)−3−(4−エチルフェニル)−1−アミノプロパン、(S)−1−(トリフルオロメチル)−4−(2−エチルフェニル)−1−アミノブタン、(S)−1−(トリフルオロメチル)−4−(3−エチルフェニル)−1−アミノブタン、(S)−1−(トリフルオロメチル)−4−(4−エチルフェニル)−1−アミノブタン、(S)−1−(トリフルオロメチル)−5−(2−エチルフェニル)−1−アミノペンタン、(S)−1−(トリフルオロメチル)−5−(3−エチルフェニル)−1−アミノペンタン、(S)−1−(トリフルオロメチル)−5−(4−エチルフェニル)−1−アミノペンタン、(S)−1−(トリフルオロメチル)−2−(2−メトキシフェニル)−1−アミノエタン、(S)−1−(トリフルオロメチル)−2−(3−メトキシフェニル)−1−アミノエタン、(S)−1−(トリフルオロメチル)−2−(4−メトキシフェニル)−1−アミノエタン、(S)−1−(トリフルオロメチル)−3−(2−メトキシフェニル)−1−アミノプロパン、(S)−1−(トリフルオロメチル)−3−(3−メトキシフェニル)−1−アミノプロパン、(S)−1−(トリフルオロメチル)−3−(4−メトキシフェニル)−1−アミノプロパン、(S)−1−(トリフルオロメチル)−4−(2−メトキシフェニル)−1−アミノブタン、(S)−1−(トリフルオロメチル)−4−(3−メトキシフェニル)−1−アミノブタン、(S)−1−(トリフルオロメチル)−4−(4−メトキシフェニル)−1−アミノブタン、(S)−1−(トリフルオロメチル)−5−(2−メトキシフェニル)−1−アミノペンタン、(S)−1−(トリフルオロメチル)−5−(3−メトキシフェニル)−1−アミノペンタン、(S)−1−(トリフルオロメチル)−5−(4−メトキシフェニル)−1−アミノペンタン、(S)−1−(トリフルオロメチル)−2−(2−エトキシフェニル)−1−アミノエタン、(S)−1−(トリフルオロメチル)−2−(3−エトキシフェニル)−1−アミノエタン、(S)−1−(トリフルオロメチル)−2−(4−エトキシフェニル)−1−アミノエタン、(S)−1−(トリフルオロメチル)−3−(2−エトキシフェニル)−1−アミノプロパン、(S)−1−(トリフルオロメチル)−3−(3−エトキシフェニル)−1−アミノプロパン、(S)−1−(トリフルオロメチル)−3−(4−エトキシフェニル)−1−アミノプロパン、(S)−1−(トリフルオロメチル)−4−(2−エトキシフェニル)−1−アミノブタン、(S)−1−(トリフルオロメチル)−4−(3−エトキシフェニル)−1−アミノブタン、(S)−1−(トリフルオロメチル)−4−(4−エトキシフェニル)−1−アミノブタン、(S)−1−(トリフルオロメチル)−5−(2−エトキシフェニル)−1−アミノペンタン、(S)−1−(トリフルオロメチル)−5−(3−エトキシフェニル)−1−アミノペンタン、(S)−1−(トリフルオロメチル)−5−(4−エトキシフェニル)−1−アミノペンタン、(S)−1−(トリフルオロメチル)−2−(2−フルオロフェニル)−1−アミノエタン、(S)−1−(トリフルオロメチル)−2−(3−フルオロフェニル)−1−アミノエタン、(S)−1−(トリフルオロメチル)−2−(4−フルオロフェニル)−1−アミノエタン、(S)−1−(トリフルオロメチル)−3−(2−フルオロフェニル)−1−アミノプロパン、(S)−1−(トリフルオロメチル)−3−(3−フルオロフェニル)−1−アミノプロパン、(S)−1−(トリフルオロメチル)−3−(4−フルオロフェニル)−1−アミノプロパン、(S)−1−(トリフルオロメチル)−4−(2−フルオロフェニル)−1−アミノブタン、(S)−1−(トリフルオロメチル)−4−(3−フルオロフェニル)−1−アミノブタン、(S)−1−(トリフルオロメチル)−4−(4−フルオロフェニル)−1−アミノブタン、(S)−1−(トリフルオロメチル)−5−(2−フルオロフェニル)−1−アミノペンタン、(S)−1−(トリフルオロメチル)−5−(3−フルオロフェニル)−1−アミノペンタン、(S)−1−(トリフルオロメチル)−5−(4−フルオロフェニル)−1−アミノペンタン、(S)−1−(トリフルオロメチル)−2−(2−クロロフェニル)−1−アミノエタン、(S)−1−(トリフルオロメチル)−2−(3−クロロフェニル)−1−アミノエタン、(S)−1−(トリフルオロメチル)−2−(4−クロロフェニル)−1−アミノエタン、(S)−1−(トリフルオロメチル)−3−(2−クロロフェニル)−1−アミノプロパン、(S)−1−(トリフルオロメチル)−3−(3−クロロフェニル)−1−アミノプロパン、(S)−1−(トリフルオロメチル)−3−(4−クロロフェニル)−1−アミノプロパン、(S)−1−(トリフルオロメチル)−4−(2−クロロフェニル)−1−アミノブタン、(S)−1−(トリフルオロメチル)−4−(3−クロロフェニル)−1−アミノブタン、(S)−1−(トリフルオロメチル)−4−(4−クロロフェニル)−1−アミノブタン、(S)−1−(トリフルオロメチル)−5−(2−クロロフェニル)−1−アミノペンタン、(S)−1−(トリフルオロメチル)−5−(3−クロロフェニル)−1−アミノペンタン、(S)−1−(トリフルオロメチル)−5−(4−クロロフェニル)−1−アミノペンタン、(S)−1−(トリフルオロメチル)−2−(2−ブロモフェニル)−1−アミノエタン、(S)−1−(トリフルオロメチル)−2−(3−ブロモフェニル)−1−アミノエタン、(S)−1−(トリフルオロメチル)−2−(4−ブロモフェニル)−1−アミノエタン、(S)−1−(トリフルオロメチル)−3−(2−ブロモフェニル)−1−アミノプロパン、(S)−1−(トリフルオロメチル)−3−(3−ブロモフェニル)−1−アミノプロパン、(S)−1−(トリフルオロメチル)−3−(4−ブロモフェニル)−1−アミノプロパン、(S)−1−(トリフルオロメチル)−4−(2−ブロモフェニル)−1−アミノブタン、(S)−1−(トリフルオロメチル)−4−(3−ブロモフェニル)−1−アミノブタン、(S)−1−(トリフルオロメチル)−4−(4−ブロモフェニル)−1−アミノブタン、(S)−1−(トリフルオロメチル)−5−(2−ブロモフェニル)−1−アミノペンタン、(S)−1−(トリフルオロメチル)−5−(3−ブロモフェニル)−1−アミノペンタン、(S)−1−(トリフルオロメチル)−5−(4−ブロモフェニル)−1−アミノペンタン、(S)−1−(トリフルオロメチル)−2−(2−シアノフェニル)−1−アミノエタン、(S)−1−(トリフルオロメチル)−2−(3−シアノフェニル)−1−アミノエタン、(S)−1−(トリフルオロメチル)−2−(4−シアノフェニル)−1−アミノエタン、(S)−1−(トリフルオロメチル)−3−(2−シアノフェニル)−1−アミノプロパン、(S)−1−(トリフルオロメチル)−3−(3−シアノフェニル)−1−アミノプロパン、(S)−1−(トリフルオロメチル)−3−(4−シアノフェニル)−1−アミノプロパン、(S)−1−(トリフルオロメチル)−4−(2−シアノフェニル)−1−アミノブタン、(S)−1−(トリフルオロメチル)−4−(3−シアノフェニル)−1−アミノブタン、(S)−1−(トリフルオロメチル)−4−(4−シアノフェニル)−1−アミノブタン、(S)−1−(トリフルオロメチル)−5−(2−シアノフェニル)−1−アミノペンタン、(S)−1−(トリフルオロメチル)−5−(3−シアノフェニル)−1−アミノペンタン、(S)−1−(トリフルオロメチル)−5−(4−シアノフェニル)−1−アミノペンタン、(S)−1−(トリフルオロメチル)−2−(2−ニトロフェニル)−1−アミノエタン、(S)−1−(トリフルオロメチル)−2−(3−ニトロフェニル)−1−アミノエタン、(S)−1−(トリフルオロメチル)−2−(4−ニトロフェニル)−1−アミノエタン、(S)−1−(トリフルオロメチル)−3−(2−ニトロフェニル)−1−アミノプロパン、(S)−1−(トリフルオロメチル)−3−(3−ニトロフェニル)−1−アミノプロパン、(S)−1−(トリフルオロメチル)−3−(4−ニトロフェニル)−1−アミノプロパン、(S)−1−(トリフルオロメチル)−4−(2−ニトロフェニル)−1−アミノブタン、(S)−1−(トリフルオロメチル)−4−(3−ニトロフェニル)−1−アミノブタン、(S)−1−(トリフルオロメチル)−4−(4−ニトロフェニル)−1−アミノブタン、(S)−1−(トリフルオロメチル)−5−(2−ニトロフェニル)−1−アミノペンタン、(S)−1−(トリフルオロメチル)−5−(3−ニトロフェニル)−1−アミノペンタン、(S)−1−(トリフルオロメチル)−5−(4−ニトロフェニル)−1−アミノペンタン等を挙げることができる。 Specific examples of the optically active amines represented by the general formula (4) of the present invention in which R 3 is an arylalkyl group which may have a substituent include, for example, (S) — 1- (trifluoromethyl) -3- (2-nitrophenyl) -1-amino-2-propene, (S) -1- (trifluoromethyl) -3-phenyl-1-aminopropane, (S)- 1- (trifluoromethyl) -4-phenyl-1-aminobutane, (S) -1- (trifluoromethyl) -5-phenyl-1-aminopentane, (S) -1- (trifluoromethyl) -6 -Phenyl-1-aminohexane, (S) -1- (trifluoromethyl) -2- (2-methylphenyl) -1-aminoethane, (S) -1- (trifluoromethyl) -2- (3- Methylphenyl) -1-amino Ethane, (S) -1- (trifluoromethyl) -2- (4-methylphenyl) -1-aminoethane, (S) -1- (trifluoromethyl) -3- (2-methylphenyl) -1- Aminopropane, (S) -1- (trifluoromethyl) -3- (3-methylphenyl) -1-aminopropane, (S) -1- (trifluoromethyl) -3- (4-methylphenyl)- 1-aminopropane, (S) -1- (trifluoromethyl) -4- (2-methylphenyl) -1-aminobutane, (S) -1- (trifluoromethyl) -4- (3-methylphenyl) -1-aminobutane, (S) -1- (trifluoromethyl) -4- (4-methylphenyl) -1-aminobutane, (S) -1- (trifluoromethyl) -5- (2-methylphenyl) -1-Aminopen (S) -1- (trifluoromethyl) -5- (3-methylphenyl) -1-aminopentane, (S) -1- (trifluoromethyl) -5- (4-methylphenyl) -1 -Aminopentane, (S) -1- (trifluoromethyl) -2- (2-ethylphenyl) -1-aminoethane, (S) -1- (trifluoromethyl) -2- (3-ethylphenyl)- 1-aminoethane, (S) -1- (trifluoromethyl) -2- (4-ethylphenyl) -1-aminoethane, (S) -1- (trifluoromethyl) -3- (2-ethylphenyl)- 1-aminopropane, (S) -1- (trifluoromethyl) -3- (3-ethylphenyl) -1-aminopropane, (S) -1- (trifluoromethyl) -3- (4-ethylphenyl) ) -1-Aminopro (S) -1- (trifluoromethyl) -4- (2-ethylphenyl) -1-aminobutane, (S) -1- (trifluoromethyl) -4- (3-ethylphenyl) -1- Aminobutane, (S) -1- (trifluoromethyl) -4- (4-ethylphenyl) -1-aminobutane, (S) -1- (trifluoromethyl) -5- (2-ethylphenyl) -1- Aminopentane, (S) -1- (trifluoromethyl) -5- (3-ethylphenyl) -1-aminopentane, (S) -1- (trifluoromethyl) -5- (4-ethylphenyl)- 1-aminopentane, (S) -1- (trifluoromethyl) -2- (2-methoxyphenyl) -1-aminoethane, (S) -1- (trifluoromethyl) -2- (3-methoxyphenyl) -1-aminoeta (S) -1- (trifluoromethyl) -2- (4-methoxyphenyl) -1-aminoethane, (S) -1- (trifluoromethyl) -3- (2-methoxyphenyl) -1- Aminopropane, (S) -1- (trifluoromethyl) -3- (3-methoxyphenyl) -1-aminopropane, (S) -1- (trifluoromethyl) -3- (4-methoxyphenyl)- 1-aminopropane, (S) -1- (trifluoromethyl) -4- (2-methoxyphenyl) -1-aminobutane, (S) -1- (trifluoromethyl) -4- (3-methoxyphenyl) -1-aminobutane, (S) -1- (trifluoromethyl) -4- (4-methoxyphenyl) -1-aminobutane, (S) -1- (trifluoromethyl) -5- (2-methoxyphenyl) -1 Aminopentane, (S) -1- (trifluoromethyl) -5- (3-methoxyphenyl) -1-aminopentane, (S) -1- (trifluoromethyl) -5- (4-methoxyphenyl)- 1-aminopentane, (S) -1- (trifluoromethyl) -2- (2-ethoxyphenyl) -1-aminoethane, (S) -1- (trifluoromethyl) -2- (3-ethoxyphenyl) -1-aminoethane, (S) -1- (trifluoromethyl) -2- (4-ethoxyphenyl) -1-aminoethane, (S) -1- (trifluoromethyl) -3- (2-ethoxyphenyl) -1-aminopropane, (S) -1- (trifluoromethyl) -3- (3-ethoxyphenyl) -1-aminopropane, (S) -1- (trifluoromethyl) -3- (4-ethoxy Phenyl) -1-aminopropane, (S) -1- (trifluoromethyl) -4- (2-ethoxyphenyl) -1-aminobutane, (S) -1- (trifluoromethyl) -4- (3- Ethoxyphenyl) -1-aminobutane, (S) -1- (trifluoromethyl) -4- (4-ethoxyphenyl) -1-aminobutane, (S) -1- (trifluoromethyl) -5- (2- Ethoxyphenyl) -1-aminopentane, (S) -1- (trifluoromethyl) -5- (3-ethoxyphenyl) -1-aminopentane, (S) -1- (trifluoromethyl) -5- ( 4-ethoxyphenyl) -1-aminopentane, (S) -1- (trifluoromethyl) -2- (2-fluorophenyl) -1-aminoethane, (S) -1- (trifluoromethyl) -2- (3-Fluorophenyl) -1-aminoethane, (S) -1- (trifluoromethyl) -2- (4-fluorophenyl) -1-aminoethane, (S) -1- (trifluoromethyl) -3- (2-Fluorophenyl) -1-aminopropane, (S) -1- (trifluoromethyl) -3- (3-fluorophenyl) -1-aminopropane, (S) -1- (trifluoromethyl)- 3- (4-Fluorophenyl) -1-aminopropane, (S) -1- (trifluoromethyl) -4- (2-fluorophenyl) -1-aminobutane, (S) -1- (trifluoromethyl) -4- (3-fluorophenyl) -1-aminobutane, (S) -1- (trifluoromethyl) -4- (4-fluorophenyl) -1-aminobutane, (S) -1- (trifluorome ) -5- (2-fluorophenyl) -1-aminopentane, (S) -1- (trifluoromethyl) -5- (3-fluorophenyl) -1-aminopentane, (S) -1- ( (Trifluoromethyl) -5- (4-fluorophenyl) -1-aminopentane, (S) -1- (trifluoromethyl) -2- (2-chlorophenyl) -1-aminoethane, (S) -1- ( Trifluoromethyl) -2- (3-chlorophenyl) -1-aminoethane, (S) -1- (trifluoromethyl) -2- (4-chlorophenyl) -1-aminoethane, (S) -1- (trifluoro Methyl) -3- (2-chlorophenyl) -1-aminopropane, (S) -1- (trifluoromethyl) -3- (3-chlorophenyl) -1-aminopropane, (S) -1- (trifluoro) (Romethyl) -3- (4-chlorophenyl) -1-aminopropane, (S) -1- (trifluoromethyl) -4- (2-chlorophenyl) -1-aminobutane, (S) -1- (trifluoromethyl) ) -4- (3-Chlorophenyl) -1-aminobutane, (S) -1- (trifluoromethyl) -4- (4-chlorophenyl) -1-aminobutane, (S) -1- (trifluoromethyl)- 5- (2-chlorophenyl) -1-aminopentane, (S) -1- (trifluoromethyl) -5- (3-chlorophenyl) -1-aminopentane, (S) -1- (trifluoromethyl)- 5- (4-chlorophenyl) -1-aminopentane, (S) -1- (trifluoromethyl) -2- (2-bromophenyl) -1-aminoethane, (S) -1- (trifluoro Methyl) -2- (3-bromophenyl) -1-aminoethane, (S) -1- (trifluoromethyl) -2- (4-bromophenyl) -1-aminoethane, (S) -1- (trifluoro) Methyl) -3- (2-bromophenyl) -1-aminopropane, (S) -1- (trifluoromethyl) -3- (3-bromophenyl) -1-aminopropane, (S) -1- ( (Trifluoromethyl) -3- (4-bromophenyl) -1-aminopropane, (S) -1- (trifluoromethyl) -4- (2-bromophenyl) -1-aminobutane, (S) -1- (Trifluoromethyl) -4- (3-bromophenyl) -1-aminobutane, (S) -1- (trifluoromethyl) -4- (4-bromophenyl) -1-aminobutane, (S) -1- (Trifluoromethyl ) -5- (2-bromophenyl) -1-aminopentane, (S) -1- (trifluoromethyl) -5- (3-bromophenyl) -1-aminopentane, (S) -1- (tri Fluoromethyl) -5- (4-bromophenyl) -1-aminopentane, (S) -1- (trifluoromethyl) -2- (2-cyanophenyl) -1-aminoethane, (S) -1- ( (Trifluoromethyl) -2- (3-cyanophenyl) -1-aminoethane, (S) -1- (trifluoromethyl) -2- (4-cyanophenyl) -1-aminoethane, (S) -1- ( (Trifluoromethyl) -3- (2-cyanophenyl) -1-aminopropane, (S) -1- (trifluoromethyl) -3- (3-cyanophenyl) -1-aminopropane, (S) -1 -(Trifluoromethyl ) -3- (4-Cyanophenyl) -1-aminopropane, (S) -1- (trifluoromethyl) -4- (2-cyanophenyl) -1-aminobutane, (S) -1- (trifluoro) Methyl) -4- (3-cyanophenyl) -1-aminobutane, (S) -1- (trifluoromethyl) -4- (4-cyanophenyl) -1-aminobutane, (S) -1- (trifluoro Methyl) -5- (2-cyanophenyl) -1-aminopentane, (S) -1- (trifluoromethyl) -5- (3-cyanophenyl) -1-aminopentane, (S) -1- ( (Trifluoromethyl) -5- (4-cyanophenyl) -1-aminopentane, (S) -1- (trifluoromethyl) -2- (2-nitrophenyl) -1-aminoethane, (S) -1- (Trifluoromethyl) 2- (3-nitrophenyl) -1-aminoethane, (S) -1- (trifluoromethyl) -2- (4-nitrophenyl) -1-aminoethane, (S) -1- (trifluoromethyl) -3- (2-nitrophenyl) -1-aminopropane, (S) -1- (trifluoromethyl) -3- (3-nitrophenyl) -1-aminopropane, (S) -1- (trifluoro Methyl) -3- (4-nitrophenyl) -1-aminopropane, (S) -1- (trifluoromethyl) -4- (2-nitrophenyl) -1-aminobutane, (S) -1- (tri Fluoromethyl) -4- (3-nitrophenyl) -1-aminobutane, (S) -1- (trifluoromethyl) -4- (4-nitrophenyl) -1-aminobutane, (S) -1- (tri Fluoromethyl) -5 (2-nitrophenyl) -1-aminopentane, (S) -1- (trifluoromethyl) -5- (3-nitrophenyl) -1-aminopentane, (S) -1- (trifluoromethyl)- 5- (4-nitrophenyl) -1-aminopentane and the like can be mentioned.

本発明の、前記一般式(4)で表される光学活性アミン類は、該当する一般式(1)で表される3−オキソピラゾリジン誘導体をスポンジニッケル等の還元触媒の存在下、開環させた後、塩酸等の酸で処理することにより製造可能である。   In the optically active amines represented by the general formula (4) of the present invention, the 3-oxopyrazolidine derivative represented by the general formula (1) is opened in the presence of a reduction catalyst such as sponge nickel. After the ring, it can be produced by treating with an acid such as hydrochloric acid.

本発明の、前記一般式(4)で表される光学活性アミン類の製造に際して、スポンジニッケルの使用量は、反応に具する3−オキソピラゾリジン誘導体に対して、1〜200重量倍量使用し、エタノール、メタノール、iso−プロパノール、tert−フ゛タノール等のアルコール系溶剤中、150〜250℃の温度範囲で10〜40時間反応を行うことにより、開環体を得る。得られた開環体は10〜35%の塩酸または10〜50%の硫酸で、100℃×2〜4日間反応することにより目的とする光学活性アミン誘導体を得る。   In the production of the optically active amine represented by the general formula (4) of the present invention, the amount of sponge nickel used is 1 to 200 times the amount of the 3-oxopyrazolidine derivative provided for the reaction. The ring-opened product is obtained by reacting in an alcohol solvent such as ethanol, methanol, iso-propanol, tert-butanol and the like at a temperature range of 150 to 250 ° C. for 10 to 40 hours. The obtained ring-opened product is reacted with 10 to 35% hydrochloric acid or 10 to 50% sulfuric acid at 100 ° C. for 2 to 4 days to obtain the target optically active amine derivative.

以下実施例により本発明を具体的に説明するが、本発明はこれらの実施例のみに限定されるものではない。なお3−オキソピラゾリジン N,N−ベタイン誘導体の調製は下記参考文献1の方法に準じた方法で調製した。
参考文献1 Sibi,M.P.;Rane,D.;Stanley,L.M.;Soeta,T.Org.Lett.2008,10,2971−2974。
また、本発明の実施に当たって、下記キラル相間移動触媒A〜Pを使用した。
EXAMPLES The present invention will be specifically described below with reference to examples, but the present invention is not limited only to these examples. The 3-oxopyrazolidine N, N-betaine derivative was prepared according to the method described in Reference 1 below.
Reference 1 Sibi, M.M. P. Rane, D .; Stanley, L .; M.M. Soeta, T .; Org. Lett. 2008, 10, 2971-2974.
In carrying out the present invention, the following chiral phase transfer catalysts A to P were used.

参考例1
5,5−ジメチルピラゾリジン−3−オンの調製
攪拌子を備えた100mlのナス型フラスコに、3−メチルクロトン酸メチル(5.00g,43.81mmol)、ヒドラジン・1水和物(2.46g,49.10mmol)及びエタノール(70ml)を仕込み、還流下7時間反応を行った。
Reference example 1
Preparation of 5,5-dimethylpyrazolidin- 3-one Into a 100 ml eggplant-shaped flask equipped with a stir bar, methyl 3-methylcrotonate (5.00 g, 43.81 mmol), hydrazine monohydrate (2 .46 g, 49.10 mmol) and ethanol (70 ml) were added, and the reaction was carried out under reflux for 7 hours.

反応終了後、減圧下、溶剤を留去することにより目的物の5,5−ジメチルピラゾリジン−3−オン(4.85g,42.49mmol)を得た(収率97%)。   After completion of the reaction, the solvent was distilled off under reduced pressure to obtain the desired 5,5-dimethylpyrazolidine-3-one (4.85 g, 42.49 mmol) (yield 97%).

参考例2
4,4−ジメチルピラゾリジン−3−オンの調製
攪拌子を備えた100mlのオートクレーブに、3−クロロ−2,2−ジメチルプロピオン酸クロリド(5.00g,32.46mmol)及びエタノール(70ml)を仕込み、0℃に冷却の後、これにトリエチルアミン(3.29g,32.46mmol)を5分かけて滴下した。
Reference example 2
Preparation of 4,4-dimethylpyrazolidin-3-one A 100 ml autoclave equipped with a stir bar was charged with 3-chloro-2,2-dimethylpropionic acid chloride (5.00 g, 32.46 mmol) and ethanol (70 ml). After cooling to 0 ° C., triethylamine (3.29 g, 32.46 mmol) was added dropwise thereto over 5 minutes.

次いで、これにトリエチルアミン(3.29g,32.46mmol)及びヒドラジン・1水和物(1.79g,35.71mmol)を仕込み、120℃で2日間反応を行った。   Next, triethylamine (3.29 g, 32.46 mmol) and hydrazine monohydrate (1.79 g, 35.71 mmol) were added thereto, and reacted at 120 ° C. for 2 days.

反応終了後、1N−塩酸で洗浄、水洗、硫酸ナトリウムで乾燥、ろ過、濃縮の後、目的物の4,4−ジメチルピラゾリジン−3−オン(0.70g,6.17mmol)を得た(収率19%)。   After completion of the reaction, the product was washed with 1N-hydrochloric acid, washed with water, dried over sodium sulfate, filtered, and concentrated to obtain the desired product 4,4-dimethylpyrazolidine-3-one (0.70 g, 6.17 mmol). (Yield 19%).

参考例3
ピラゾリジン3−オンの調製
参考例1と同じ反応装置を用い、3−メチルクロトン酸メチルに替えて、アクリル酸メチル(5.00g,58.08mmol)に替えた以外、参考例1と同じ反応操作を行い目的物のピラゾリジン−3−オン(2.35g,27.30mmol)を得た(収率47%)。
Reference example 3
Preparation of pyrazolidin-3-one The same reaction procedure as in Reference Example 1 except that methyl acrylate (5.00 g, 58.08 mmol) was used instead of methyl 3-methylcrotonate using the same reaction apparatus as in Reference Example 1. To obtain the target pyrazolidin-3-one (2.35 g, 27.30 mmol) (yield 47%).

参考例4
1−ベンジリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタインの調製
Reference example 4
Preparation of 1-benzylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine

攪拌子を備えた10mlの丸底フラスコに、室温下、参考例1で調製した5,5−ジメチルピラゾリジン−3−オン(200 mg,1.75mmol)をエタノール(0.5ml)に溶解させ、これにベンズアルデヒド(199mg,1.88mmol)を加え、オイルバス上で加熱下、70℃で一晩反応を行った。反応終了後、溶剤を留去、次いでシリカゲルカラムクロマトグラフィー(ジクロロメタン/メタノール=9/1 vol/vol)で精製することにより目的物の1−ベンジリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン(289mg,1.43mmol)を白色固体として得た(収率80%)。この化合物の同定は、参考文献1及び2に従い実施した。
H−NMR(CDCl,400MHz)δ1.76(s,6H),2.79(s,2H),7.04(s,1H),7.49−7.51(m,3H),8.35−8.38(m,2H)。
13C−NMR(CDCl,100MHz)δ29.1,44.6,74.0,129.0,129.7,129.9,131.9,132.0,181.9。
IR(KBr)3064,2976,1661,1589,1451,1299,1180,1160,1091,944,889,862,808,762,694,674,642,613cm−1
mp=140−142℃。
HRMS calcd. for C1215O(M+H):203.1179 Found: 203.1181。
Dissolve 5,5-dimethylpyrazolidine-3-one (200 mg, 1.75 mmol) prepared in Reference Example 1 in ethanol (0.5 ml) at room temperature in a 10 ml round bottom flask equipped with a stir bar. Benzaldehyde (199 mg, 1.88 mmol) was added thereto, and the reaction was carried out overnight at 70 ° C. under heating on an oil bath. After completion of the reaction, the solvent was distilled off, followed by purification by silica gel column chromatography (dichloromethane / methanol = 9/1 vol / vol) to obtain the desired 1-benzylidene-5,5-dimethyl-3-oxopyrazolidine. N, N-betaine (289 mg, 1.43 mmol) was obtained as a white solid (yield 80%). This compound was identified according to References 1 and 2.
1 H-NMR (CDCl 3 , 400 MHz) δ 1.76 (s, 6H), 2.79 (s, 2H), 7.04 (s, 1H), 7.49-7.51 (m, 3H), 8.35-8.38 (m, 2H).
13 C-NMR (CDCl 3 , 100 MHz) δ 29.1, 44.6, 74.0, 129.0, 129.7, 129.9, 131.9, 132.0, 181.9.
IR (KBr) 3064, 2976, 1661, 1589, 1451, 1299, 1180, 1160, 1091, 944, 889, 862, 808, 762, 694, 674, 642, 613 cm −1 .
mp = 140-142 ° C.
HRMS calcd. for C 12 H 15 N 2 O (M + H +): 203.1179 Found: 203.1181.

参考例5
1−ベンジリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタインの調製
Reference Example 5
Preparation of 1-benzylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine

参考例4と同じ反応装置を用い、5,5−ジメチルピラゾリジン−3−オンに替えて4,4−ジメチルピラゾリジン−3−オンを用いエタノールに替えてメタノール中で室温下、10分反応を行うことにより目的物の1−ベンジリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタイン(260mg,1.25mmol)を得た(収率72%)。   Using the same reaction apparatus as in Reference Example 4, instead of 5,5-dimethylpyrazolidine-3-one, 4,4-dimethylpyrazolidine-3-one was used instead of ethanol at room temperature in methanol. By subjecting to a partial reaction, 1-benzylidene-4,4-dimethyl-3-oxopyrazolidine N, N-betaine (260 mg, 1.25 mmol) as a target product was obtained (yield 72%).

参考例6
1−ベンジリデン−3−オキソピラゾリジン N,N−ベタインの調製
Reference Example 6
Preparation of 1-benzylidene-3-oxopyrazolidine N, N-betaine

参考例4と同じ反応装置を用い、5,5−ジメチルピラゾリジン−3−オンに替えてピラゾリジン−3−オンを用いエタノールに替えてメタノール中で室温下、20分反応を行うことにより目的物の1−ベンジリデン−3−オキソピラゾリジン N,N−ベタイン(232mg,1.33mmol)を得た(収率76%)。   By using the same reaction apparatus as in Reference Example 4, instead of 5,5-dimethylpyrazolidine-3-one, pyrazolidin-3-one was used instead of ethanol, and the reaction was carried out in methanol at room temperature for 20 minutes. 1-benzylidene-3-oxopyrazolidine N, N-betaine (232 mg, 1.33 mmol) was obtained (76% yield).

参考例7
1−(2−ナフチル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタインの調製
Reference Example 7
Preparation of 1- (2-naphthyl) methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine

参考例4と同じ反応装置を用い、ベンズアルデヒドに替えて2−ナフトアルデヒドに替えた以外、参考例4と同じ操作を行い目的物の1−(2−ナフチル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタインを得た(灰白色固体、収率91%)。
H−NMR(CDCl,200MHz)δ1.75(s,6H),2.77(s,2H),7.21(s,1H),7.46−7.60(m,2H),7.79−7.87(m,2H),7.94−7.98(m,1H),8.13(dd,J=1.8,8.6Hz,1H),9.15(s,1H)。
13C−NMR(CDCl,150.9MHz)δ28.8,44.4,73.8,126.7,126.8,127.3,127.5,128.2,128.3,129.5,129.7,132.8,133.0,134.4。
IR(KBr)3057,2978,1660,1625,1580,1499,1472,1421,1314,1248,1171,1142,1092,991,923,881,814,758,671,652cm−1
mp=200.5−202℃。
MS (EI,m/z)252(M)。
1- (2-naphthyl) methylidene-5,5-dimethyl-3, which was the target product, was prepared by performing the same operation as in Reference Example 4 except that benzaldehyde was replaced by 2-naphthaldehyde using the same reaction apparatus as in Reference Example 4. -Oxopyrazolidine N, N-betaine was obtained (off-white solid, yield 91%).
1 H-NMR (CDCl 3 , 200 MHz) δ 1.75 (s, 6H), 2.77 (s, 2H), 7.21 (s, 1H), 7.46-7.60 (m, 2H), 7.79-7.87 (m, 2H), 7.94-7.98 (m, 1H), 8.13 (dd, J = 1.8, 8.6 Hz, 1H), 9.15 (s) , 1H).
13 C-NMR (CDCl 3 , 150.9 MHz) δ 28.8, 44.4, 73.8, 126.7, 126.8, 127.3, 127.5, 128.2, 128.3, 129. 5, 129.7, 132.8, 133.0, 134.4.
IR (KBr) 3057, 2978, 1660, 1625, 1580, 1499, 1472, 1421, 1314, 1248, 1171, 1142, 1092, 991, 923, 881, 814, 758, 671, 652 cm −1 .
mp = 200.5-202 ° C.
MS (EI, m / z) 252 (M <+> ).

参考例8
1−(6−メトキシ−2−ナフチル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタインの調製
Reference Example 8
Preparation of 1- (6-methoxy-2-naphthyl) methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine

参考例4と同じ反応装置を用い、ベンズアルデヒドに替えて6−メトキシナフト−2−アルデヒドに替えた以外、参考例4と同じ操作を行い目的物の1−(6−メトキシ−2−ナフチル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタインを得た(灰白色固体、収率50%)。
H−NMR(CDCl,200MHz)δ1.74(s,6H),2.77(s,2H),3.93(s,3H),7.10−7.20(m,3H),7.75(d,J=8.6Hz,1H),7.86(d,J=9.0Hz,1H),8.12(dd,J=1.9,8.5Hz,1H),9.04(s,1H)。
13C−NMR(CDCl,150.9MHz)δ28.9,44.5,55.4,73.4,105.7,119.7,124.6,127.0,128.1,128.3,130.1,131.2,132.9,136.2,159.8,181.6。
IR(KBr)3055,2972,1658,1623,1587,1484,1425,1385,1320,1270,1221,1173,1147,1096,1025,919,845,809,666cm−1
mp=183−185℃。
MS (EI,m/z)282(M)。
The same reaction apparatus as in Reference Example 4 was used, except that benzaldehyde was replaced with 6-methoxynaphth-2-aldehyde, and the same operation as in Reference Example 4 was performed to obtain the target 1- (6-methoxy-2-naphthyl) methylidene. -5,5-Dimethyl-3-oxopyrazolidine N, N-betaine was obtained (off-white solid, yield 50%).
1 H-NMR (CDCl 3 , 200 MHz) δ 1.74 (s, 6H), 2.77 (s, 2H), 3.93 (s, 3H), 7.10-7.20 (m, 3H), 7.75 (d, J = 8.6 Hz, 1H), 7.86 (d, J = 9.0 Hz, 1H), 8.12 (dd, J = 1.9, 8.5 Hz, 1H), 9 .04 (s, 1H).
13 C-NMR (CDCl 3 , 150.9 MHz) δ 28.9, 44.5, 55.4, 73.4, 105.7, 119.7, 124.6, 127.0, 128.1, 128. 3, 130.1, 131.2, 132.9, 136.2, 159.8, 181.6.
IR (KBr) 3055, 2972, 1658, 1623, 1587, 1484, 1425, 1385, 1320, 1270, 1221, 1173, 1147, 1096, 1025, 919, 845, 809, 666 cm −1 .
mp = 183-185 ° C.
MS (EI, m / z) 282 (M <+> ).

参考例9
1−(1−ナフチル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタインの調製
Reference Example 9
Preparation of 1- (1-naphthyl) methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine

参考例4と同じ反応装置を用い、ベンズアルデヒドに替えて1−ナフトアルデヒドに替えた以外、参考例4と同じ操作を行い目的物の1−(1−ナフチル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタインを得た(灰白色固体、収率68%)。
H−NMR(CDCl,200MHz)δ1.81(s,6H),2.78(s,2H),7.50−7.66(m,3H),7.87−7.94(m,3H),8.06(d,J=8.06Hz,1H),9.42(d,J=7.6Hz,1H)。
13C−NMR(CDCl,150.9MHz)δ29.1,44.3,74.3,121.2,124.3,125.2,125.6,126.1,127.5,129.5,131.2,131.3,132.3,133.3,181.9。
IR(KBr)3040,2973,1651,1569,1508,1421,1310,1145,1100,1018,983,954,858,828,797,775,740,675,618cm−1
mp=218−221℃。
MS(EI,m/z)252(M)。
1- (1-naphthyl) methylidene-5,5-dimethyl-3 was obtained by performing the same operation as in Reference Example 4 except that benzaldehyde was replaced with 1-naphthaldehyde using the same reaction apparatus as in Reference Example 4. -Oxopyrazolidine N, N-betaine was obtained (off-white solid, yield 68%).
1 H-NMR (CDCl 3 , 200 MHz) δ1.81 (s, 6H), 2.78 (s, 2H), 7.50-7.66 (m, 3H), 7.87-7.94 (m 3H), 8.06 (d, J = 8.06 Hz, 1H), 9.42 (d, J = 7.6 Hz, 1H).
13 C-NMR (CDCl 3 , 150.9 MHz) δ 29.1, 44.3, 74.3, 121.2, 124.3, 125.2, 125.6, 126.1, 127.5, 129. 5, 131.2, 131.3, 132.3, 133.3, 181.9.
IR (KBr) 3040, 2973, 1651, 1569, 1508, 1421, 1310, 1145, 1100, 1018, 983, 954, 858, 828, 797, 775, 740, 675, 618 cm −1 .
mp = 218-221 ° C.
MS (EI, m / z) 252 (M <+> ).

参考例10
1−(2−メチルフェニル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタインの調製
Reference Example 10
Preparation of 1- (2-methylphenyl) methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine

参考例4と同じ反応装置を用い、ベンズアルデヒドに替えて2−メチルベンズアルデヒドに替えた以外、参考例4と同じ操作を行い目的物の1−(2−メチルフェニル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタインを得た(白色固体、収率70%)。
H−NMR(CDCl,200MHz)δ1.74(s,6H),2.50(s,3H),2.74(s,2H),7.20−7.35(m,4H),9.10−9.15(m,1H)。
13C−NMR(CDCl,150.9MHz)δ19.7,29.0,44.2,73.9,126.5,126.7,127.7,130.3,131.2,131.5,138.0,181.6。
IR(KBr)3223,3066,2967,2873,2160,1659,1583,1565,1464,1315,1150,1082,949,875,763,677cm−1
mp=161−162℃。
MS(EI,m/z)216(M)。
Using the same reaction apparatus as in Reference Example 4, the same operation as in Reference Example 4 was carried out except that 2-methylbenzaldehyde was used instead of benzaldehyde, and the target product 1- (2-methylphenyl) methylidene-5,5-dimethyl- 3-Oxopyrazolidine N, N-betaine was obtained (white solid, yield 70%).
1 H-NMR (CDCl 3 , 200 MHz) δ 1.74 (s, 6H), 2.50 (s, 3H), 2.74 (s, 2H), 7.20-7.35 (m, 4H), 9.10-9.15 (m, 1H).
13 C-NMR (CDCl 3 , 150.9 MHz) δ 19.7, 29.0, 44.2, 73.9, 126.5, 126.7, 127.7, 130.3, 131.2, 131. 5, 138.0, 181.6.
IR (KBr) 3223, 3066, 2967, 2873, 2160, 1659, 1583, 1565, 1464, 1315, 1150, 1082, 949, 875, 763, 677 cm −1 .
mp = 161-162 ° C.
MS (EI, m / z) 216 (M <+> ).

参考例11
1−(3−メチルフェニル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタインの調製
Reference Example 11
Preparation of 1- (3-methylphenyl) methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine

参考例4と同じ反応装置を用い、ベンズアルデヒドに替えて3−メチルベンズアルデヒドに替えた以外、参考例4と同じ操作を行い目的物の1−(3−メチルフェニル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタインを得た(白色固体、収率84%)。
H−NMR(CDCl,200MHz)δ1.72(s,6H),2.40(s,3H),2.73(s,2H),7.06(s,1H),7.25−7.39(m,2H),8.09(d,J=7.4Hz,1H),8.22(s,1H)。
13C−NMR(CDCl,150.9MHz)δ21.3,28.8,44.4,73.6,128.5,129.0,129.4,130.0,131.9,132.7,138.6,181.6。
IR(KBr)3049,2971,1660,1591,1572,1457,1430,1373,1323,1303,1177,1139,1081,933,821,792,672cm−1
mp=197−199℃。
MS(EI,m/z)216(M)。
The same reaction apparatus as in Reference Example 4 was used, except that benzaldehyde was replaced with 3-methylbenzaldehyde, and the same operation as in Reference Example 4 was performed to obtain 1- (3-methylphenyl) methylidene-5,5-dimethyl- 3-Oxopyrazolidine N, N-betaine was obtained (white solid, 84% yield).
1 H-NMR (CDCl 3 , 200 MHz) δ 1.72 (s, 6H), 2.40 (s, 3H), 2.73 (s, 2H), 7.06 (s, 1H), 7.25- 7.39 (m, 2H), 8.09 (d, J = 7.4 Hz, 1H), 8.22 (s, 1H).
13 C-NMR (CDCl 3 , 150.9 MHz) δ 21.3, 28.8, 44.4, 73.6, 128.5, 129.0, 129.4, 130.0, 131.9, 132. 7, 138.6, 181.6.
IR (KBr) 3049, 2971, 1660, 1591, 1572, 1457, 1430, 1373, 1323, 1303, 1177, 1139, 1081, 933, 821, 792, 672 cm −1 .
mp = 197-199 ° C.
MS (EI, m / z) 216 (M <+> ).

参考例12
1−(4−メチルフェニル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタインの調製
Reference Example 12
Preparation of 1- (4-methylphenyl) methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine

参考例4と同じ反応装置を用い、ベンズアルデヒドに替えて4−メチルベンズアルデヒドに替えた以外、参考例4と同じ操作を行い目的物の1−(4−メチルフェニル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタインを得た(灰白色固体、収率77%)。
H−NMR(CDCl,200MHz)δ1.71(s,6H),2.40(s,3H),2.72(s,2H),7.07(s,1H),7.26(d,J=8.2Hz,2H),8.25(d,J=8.2Hz,2H)。
13C−NMR(CDCl,100MHz)δ22.0,29.1,44.7,73.6,127.1,129.8,130.1,132.0,143.1,181.7。
IR(KBr)3056,2972,1656,1593,1558,1456,1435,1296,1180,1086,945,904,863,817,676,634cm−1
mp=203−205℃。
HRMS calcd. for C1317:217.1355 Found:217.1333。
The same reaction apparatus as in Reference Example 4 was used, except that 4-methylbenzaldehyde was used instead of benzaldehyde, and the same operation as in Reference Example 4 was performed to obtain 1- (4-methylphenyl) methylidene-5,5-dimethyl- 3-Oxopyrazolidine N, N-betaine was obtained (off-white solid, yield 77%).
1 H-NMR (CDCl 3 , 200 MHz) δ 1.71 (s, 6H), 2.40 (s, 3H), 2.72 (s, 2H), 7.07 (s, 1H), 7.26 ( d, J = 8.2 Hz, 2H), 8.25 (d, J = 8.2 Hz, 2H).
13 C-NMR (CDCl 3 , 100 MHz) δ 22.0, 29.1, 44.7, 73.6, 127.1, 129.8, 130.1, 132.0, 143.1, 181.7.
IR (KBr) 3056, 2972, 1656, 1593, 1558, 1456, 1435, 1296, 1180, 1086, 945, 904, 863, 817, 676, 634 cm- 1 .
mp = 203-205 ° C.
HRMS calcd. for C 13 H 17 N 2 O +: 217.1355 Found: 217.1333.

参考例13
1−(3−メトキシフェニル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタインの調製
Reference Example 13
Preparation of 1- (3-methoxyphenyl) methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine

参考例4と同じ反応装置を用い、ベンズアルデヒドに替えて3−メトキシベンズアルデヒドに替えた以外、参考例4と同じ操作を行い目的物の1−(3−メトキシフェニル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタインを得た(白色固体、収率88%)。
H−NMR(CDCl,200MHz)δ1.73,(s,6H),2.73,(s,2H),3.85(s,3H),7.02(dd,J=2.5,7.7Hz,1H),7.09(s,1H),7.35(t,J=8.0Hz,1H),7.75(d,J=7.8Hz,1H),8.12(t,J=2.0Hz,1H)。
13C−NMR(CDCl,50.3MHz)δ29.0,44.4,55.5,73.8,115.3,118.4,124.2,129.3,129.5,130.4,159.3,181.1。
IR(KBr)3044,3006,2969,1660,1585,1459,1412,1314,1293,1247,1164,1088,1045,984,957,788,672cm−1
mp=137−139℃。
MS(EI,m/z)232(M)。
The same reaction apparatus as in Reference Example 4 was used, except that benzaldehyde was replaced by 3-methoxybenzaldehyde, and the same operation as in Reference Example 4 was performed to obtain the target 1- (3-methoxyphenyl) methylidene-5,5-dimethyl- 3-Oxopyrazolidine N, N-betaine was obtained (white solid, yield 88%).
1 H-NMR (CDCl 3 , 200 MHz) δ 1.73, (s, 6H), 2.73, (s, 2H), 3.85 (s, 3H), 7.02 (dd, J = 2.5 , 7.7 Hz, 1 H), 7.09 (s, 1 H), 7.35 (t, J = 8.0 Hz, 1 H), 7.75 (d, J = 7.8 Hz, 1 H), 8.12 (T, J = 2.0 Hz, 1H).
13 C-NMR (CDCl 3 , 50.3 MHz) δ 29.0, 44.4, 55.5, 73.8, 115.3, 118.4, 124.2, 129.3, 129.5, 130. 4, 159.3, 181.1.
IR (KBr) 3044, 3006, 2969, 1660, 1585, 1459, 1412, 1314, 1293, 1247, 1164, 1088, 1045, 984, 957, 788, 672 cm −1 .
mp = 137-139 ° C.
MS (EI, m / z) 232 (M <+> ).

参考例14
1−(4−メトキシフェニル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタインの調製
Reference Example 14
Preparation of 1- (4-methoxyphenyl) methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine

参考例4と同じ反応装置を用い、ベンズアルデヒドに替えて4−メトキシベンズアルデヒドに替えた以外、参考例4と同じ操作を行い目的物の1−(4−メトキシフェニル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタインを得た(白色固体、収率94%)。
H−NMR(CDCl,400MHz)δ1.68(s,6H),2.74(s,2H),3.85(s,3H),6.94(d,J=8.7Hz,2H),7.08(s,1H),8.33(d,J=8.7Hz,2H)。
13C−NMR(CDCl,100MHz)δ29.1,44.9,55.7,73.1,114.4,122.7,129.8,134.0,162.6,181.5。
IR(KBr)3068,2983,1932,2840,1660,1606,1512,1439,1307,1259,1175,1085,1028,829,679cm−1
mp=194−196℃。
HRMS calcd. for C1317 :233.1285 Found:233.1285。
The same reaction apparatus as in Reference Example 4 was used, except that 4-methoxybenzaldehyde was used instead of benzaldehyde, and the same operation as in Reference Example 4 was performed to obtain 1- (4-methoxyphenyl) methylidene-5,5-dimethyl- 3-Oxopyrazolidine N, N-betaine was obtained (white solid, 94% yield).
1 H-NMR (CDCl 3 , 400 MHz) δ 1.68 (s, 6H), 2.74 (s, 2H), 3.85 (s, 3H), 6.94 (d, J = 8.7 Hz, 2H) ), 7.08 (s, 1H), 8.33 (d, J = 8.7 Hz, 2H).
13 C-NMR (CDCl 3 , 100 MHz) δ 29.1, 44.9, 55.7, 73.1, 114.4, 122.7, 129.8, 134.0, 162.6, 181.5.
IR (KBr) 3068, 2983, 1932, 2840, 1660, 1606, 1512, 1439, 1307, 1259, 1175, 1085, 1028, 829, 679 cm −1 .
mp = 194-196 ° C.
HRMS calcd. for C 13 H 17 N 2 O 2 +: 233.1285 Found: 233.1285.

参考例15
1−(4−iso−プロピルフェニル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタインの調製
Reference Example 15
Preparation of 1- (4-Iso-propylphenyl) methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine

参考例4と同じ反応装置を用い、ベンズアルデヒドに替えて4−イソプロピルベンズアルデヒドに替えた以外、参考例4と同じ操作を行い目的物の1−(4−iso−プロピルフェニル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタインを得た(白色固体、収率81%)。
H−NMR(CDCl,200MHz)δ1.26(d,J=6.6Hz,6H),1.71(s,6H),2.73(s,2H),2.95(sept,J=6.9Hz,1H),7.08(s,1H),7.31(d,J=8.4Hz,2H),8.28(d,J=8.4Hz,2H)。
13C−NMR(CDCl,50.3MHz)δ23.7,29.0,34.4,44.6,73.3,126.6,127.0,129.8,131.6,153.2,181.0。
IR(KBr)3404(br),3049,2962,2870,1658,1587,1557,1428,1310,1187,1144,1082,1018,949,835,723,677,632cm−1
mp=185−187℃。
MS(EI,m/z)244(M)。
The same reaction apparatus as in Reference Example 4 was used, except that 4-isopropylbenzaldehyde was used instead of benzaldehyde, and the same operation as in Reference Example 4 was performed to obtain 1- (4-iso-propylphenyl) methylidene-5,5- Dimethyl-3-oxopyrazolidine N, N-betaine was obtained (white solid, 81% yield).
1 H-NMR (CDCl 3 , 200 MHz) δ 1.26 (d, J = 6.6 Hz, 6H), 1.71 (s, 6H), 2.73 (s, 2H), 2.95 (sept, J = 6.9 Hz, 1 H), 7.08 (s, 1 H), 7.31 (d, J = 8.4 Hz, 2 H), 8.28 (d, J = 8.4 Hz, 2 H).
13 C-NMR (CDCl 3 , 50.3 MHz) δ 23.7, 29.0, 34.4, 44.6, 73.3, 126.6, 127.0, 129.8, 131.6, 153. 2, 181.0.
IR (KBr) 3404 (br), 3049, 2962, 2870, 1658, 1587, 1557, 1428, 1310, 1187, 1144, 1082, 1018, 949, 835, 723, 677, 632 cm −1 .
mp = 185-187 ° C.
MS (EI, m / z) 244 (M <+> ).

参考例16
1−(4−tert−ブチルフェニル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタインの調製
Reference Example 16
Preparation of 1- (4-tert-butylphenyl) methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine

参考例4と同じ反応装置を用い、ベンズアルデヒドに替えて4−tert−ブチルベンズアルデヒドに替えた以外、参考例4と同じ操作を行い目的物の1−(4−tert−ブチルフェニル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタインを得た(灰白色固体、収率86%)。
H−NMR(CDCl,200MHz)δ1.33(s,9H),1.71(s,6H),2.73(s,2H),7.02(s,1H),7.48(d,J=8.6Hz,2H),8.27(d,J=8.8Hz,2H)。
13C−NMR(CDCl,150.9MHz)δ28.8,30.9,35.1,44.5,73.3,125.7,126.8,129.8,131.6,155.7,181.4。
IR(KBr)2968,1663,1590,1555,1427,1311,1107,1083,948,885,826,692,677,642cm−1
mp=225−227℃。
MS(EI,m/z)258(M)。
The same reaction apparatus as in Reference Example 4 was used, except that 4-tert-butylbenzaldehyde was used instead of benzaldehyde, and the same operation as in Reference Example 4 was performed to obtain 1- (4-tert-butylphenyl) methylidene-5 5-Dimethyl-3-oxopyrazolidine N, N-betaine was obtained (off-white solid, yield 86%).
1 H-NMR (CDCl 3 , 200 MHz) δ 1.33 (s, 9H), 1.71 (s, 6H), 2.73 (s, 2H), 7.02 (s, 1H), 7.48 ( d, J = 8.6 Hz, 2H), 8.27 (d, J = 8.8 Hz, 2H).
13 C-NMR (CDCl 3 , 150.9 MHz) δ 28.8, 30.9, 35.1, 44.5, 73.3, 125.7, 126.8, 129.8, 131.6, 155. 7, 181.4.
IR (KBr) 2968, 1663, 1590, 1555, 1427, 1311, 1107, 1083, 948, 885, 826, 692, 677, 642 cm −1 .
mp = 225-227 ° C.
MS (EI, m / z) 258 (M <+> ).

参考例17
1−(3,4−ジメチルフェニル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタインの調製
Reference Example 17
Preparation of 1- (3,4-dimethylphenyl) methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine

参考例4と同じ反応装置を用い、ベンズアルデヒドに替えて3,4−ジメチルベンズアルデヒドに替えた以外、参考例4と同じ操作を行い目的物の1−(3,4−ジメチルフェニル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタインを得た(灰白色固体、収率84%)。
H−NMR(CDCl,200MHz)δ1.71(s,6H),2.31(s,6H),2.72(s,2H),7.01(s,1H),7.21(d,J=7.8Hz,1H),8.06−8.11(m,2H)。
13C−NMR(CDCl,150.9MHz)δ19.6,20.0,28.8,44.4,73.2,127.1,129.5,130.0,130.3,132.4,137.2,141.6,181.4。
IR(KBr)3056,2973,1655,1588,1507,1457,1428,1374,1308,1125,1079,929,861,822,712,674cm−1
mp=204.5−206℃。
MS(EI,m/z)230(M)。
The same reaction apparatus as in Reference Example 4 was used, except that benzaldehyde was replaced with 3,4-dimethylbenzaldehyde, and the same operation as in Reference Example 4 was carried out to obtain the target 1- (3,4-dimethylphenyl) methylidene-5. 5-Dimethyl-3-oxopyrazolidine N, N-betaine was obtained (off-white solid, 84% yield).
1 H-NMR (CDCl 3 , 200 MHz) δ 1.71 (s, 6H), 2.31 (s, 6H), 2.72 (s, 2H), 7.01 (s, 1H), 7.21 ( d, J = 7.8 Hz, 1H), 8.06-8.11 (m, 2H).
13 C-NMR (CDCl 3 , 150.9 MHz) δ 19.6, 20.0, 28.8, 44.4, 73.2, 127.1, 129.5, 130.0, 130.3, 132. 4, 137.2, 141.6, 181.4.
IR (KBr) 3056, 2973, 1655, 1588, 1507, 1457, 1428, 1374, 1308, 1125, 1079, 929, 861, 822, 712, 674 cm −1 .
mp = 204.5-206 ° C.
MS (EI, m / z) 230 (M <+> ).

参考例18
1−(4−フルオロフェニル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタインの調製
Reference Example 18
Preparation of 1- (4-fluorophenyl) methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine

参考例4と同じ反応装置を用い、ベンズアルデヒドに替えて4−フルオロベンズアルデヒドに替えた以外、参考例4と同じ操作を行い目的物の1−(4−フルオロフェニル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタインを得た(白色固体、収率68%)。
H−NMR(CDCl,200MHz)δ1.73(s,6H),2.74(s,2H),7.06−7.19(m,3H),8.41(dd,J=5.7,6.6Hz,2H)。
13C−NMR(CDCl,150.9MHz)δ28.7,44.3,73.7,115.9(d,J=21.1Hz),125.9(d,J=3.0Hz),128.7,134.1(d,J=9.1Hz),164.1(d,J=255.0Hz),181.6。
19F−NMR(CDCl,188MHz)δ−104.7(s,1F)。
IR(KBr)3059,2978,1662,1598,1577,1506,1438,1374,1326,1306,1225,1163,1088,952,839,774,681,625cm−1
mp=211−213℃
MS(EI,m/z)220(M)。
The same reaction apparatus as in Reference Example 4 was used, except that 4-fluorobenzaldehyde was used instead of benzaldehyde, and the same operation as in Reference Example 4 was performed to obtain 1- (4-fluorophenyl) methylidene-5,5-dimethyl- 3-Oxopyrazolidine N, N-betaine was obtained (white solid, yield 68%).
1 H-NMR (CDCl 3 , 200 MHz) δ1.73 (s, 6H), 2.74 (s, 2H), 7.06-7.19 (m, 3H), 8.41 (dd, J = 5 .7, 6.6 Hz, 2H).
13 C-NMR (CDCl 3 , 150.9 MHz) δ 28.7, 44.3, 73.7, 115.9 (d, J = 21.1 Hz), 125.9 (d, J = 3.0 Hz), 128.7, 134.1 (d, J = 9.1 Hz), 164.1 (d, J = 255.0 Hz), 181.6.
19 F-NMR (CDCl 3 , 188 MHz) δ-104.7 (s, 1F).
IR (KBr) 3059, 2978, 1662, 1598, 1577, 1506, 1438, 1374, 1326, 1306, 1225, 1163, 1088, 952, 839, 774, 681, 625 cm −1 .
mp = 211-213 ° C
MS (EI, m / z) 220 (M <+> ).

参考例19
1−(4−クロロフェニル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタインの調製
Reference Example 19
Preparation of 1- (4-chlorophenyl) methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine

参考例4と同じ反応装置を用い、ベンズアルデヒドに替えて4−クロロベンズアルデヒドに替えた以外、参考例4と同じ操作を行い目的物の1−(4−クロロフェニル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタインを得た(灰白色固体、収率57%)。
H−NMR(CDCl,400MHz)δ1.70(s,6H),2.72(s,2H),6.97(s,1H),7.40−7.43(dt,J=8.8,2.5Hz,2H),8.27−8.31(dt,J=8.8,2.5Hz,2H)。
13C−NMR(CDCl,100MHz)δ29.1,44.5,74.3,127.7,128.2,129.2,132.8,137.9,181.9。
IR(KBr)3058,2977,1663,1587,1557,1490,1437,1329,1306,1288,1092,1014,950,831,688,674cm−1
mp=199−201℃。
HRMS calcd. for C1214ClN:237.0789 Found:237.0784。
1- (4-Chlorophenyl) methylidene-5,5-dimethyl-3 was obtained by performing the same operation as in Reference Example 4 except that 4-chlorobenzaldehyde was used instead of benzaldehyde, using the same reaction apparatus as in Reference Example 4. -Oxopyrazolidine N, N-betaine was obtained (off-white solid, 57% yield).
1 H-NMR (CDCl 3 , 400 MHz) δ 1.70 (s, 6H), 2.72 (s, 2H), 6.97 (s, 1H), 7.40-7.43 (dt, J = 8 .8, 2.5 Hz, 2H), 8.27-8.31 (dt, J = 8.8, 2.5 Hz, 2H).
13 C-NMR (CDCl 3 , 100 MHz) δ 29.1, 44.5, 74.3, 127.7, 128.2, 129.2, 132.8, 137.9, 181.9.
IR (KBr) 3058, 2977, 1663, 1587, 1557, 1490, 1437, 1329, 1306, 1288, 1092, 1014, 950, 831, 688, 674 cm −1 .
mp = 199-201 ° C.
HRMS calcd. for C 12 H 14 ClN 2 O + : 237.0789 Found: 237.0784.

参考例20
1−(4−ブロモフェニル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタインの調製
Reference Example 20
Preparation of 1- (4-bromophenyl) methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine

参考例4と同じ反応装置を用い、ベンズアルデヒドに替えて4−ブロモベンズアルデヒドに替えた以外、参考例4と同じ操作を行い目的物の1−(4−ブロモフェニル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタインを得た(灰白色固体、収率85%)。
H−NMR(CDCl,400MHz)δ1.70(s,6H),2.75(s,2H),7.02(s,1H),7.57−7.60(dt,J=8.8,2.5Hz,2H),8.20−8.23(dt,J=8.8,2.5Hz,2H)。
13C−NMR(CDCl,100MHz)δ29.0,44.5,74.3,126.5,128.0,128.7,132.2,133.0,181.7。
IR(KBr)3049,2970,1669,1586,1552,1487,1464,1435,1399,1323,1308,1285,1089,819,706,678,653,623cm−1
mp=197−197℃。
HRMS calcd. for C1213BrNNaO:303.0103 Found:303.0096。
The same reaction apparatus as in Reference Example 4 was used, except that 4-bromobenzaldehyde was used instead of benzaldehyde, and the same operation as in Reference Example 4 was performed to obtain 1- (4-bromophenyl) methylidene-5,5-dimethyl- 3-Oxopyrazolidine N, N-betaine was obtained (off-white solid, yield 85%).
1 H-NMR (CDCl 3 , 400 MHz) δ 1.70 (s, 6H), 2.75 (s, 2H), 7.02 (s, 1H), 7.57-7.60 (dt, J = 8 .8, 2.5 Hz, 2H), 8.20-8.23 (dt, J = 8.8, 2.5 Hz, 2H).
13 C-NMR (CDCl 3 , 100 MHz) δ 29.0, 44.5, 74.3, 126.5, 128.0, 128.7, 132.2, 133.0, 181.7.
IR (KBr) 3049, 2970, 1669, 1586, 1552, 1487, 1464, 1435, 1399, 1323, 1308, 1285, 1089, 819, 706, 678, 653, 623 cm −1 .
mp = 197-197 ° C.
HRMS calcd. for C 12 H 13 BrN 2 NaO +: 303.0103 Found: 303.0096.

参考例21
1−(3−フェニルプロピリデン−2−エン)−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタインの調製
Reference Example 21
Preparation of 1- (3-phenylpropylidene-2-ene) -5,5-dimethyl-3-oxopyrazolidine N, N-betaine

参考例4と同じ反応装置を用い、ベンズアルデヒドに替えてシンナムアルデヒドに替えた以外、参考例4と同じ操作を行い目的物の1−(3−フェニルプロピリデン−2−エン)−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタインを得た(黄色固体、収率99%)。
H−NMR(CDCl,200MHz)δ1.65(s,6H),2.75(s,2H),6.92(d,J=9.6Hz,1H),7.09(d,J=16.2Hz,1H),7.35−7.38(m,3H),7.50−7.55(m,2H),7.66(dd,J=9.6,16.2Hz,1H)。
13C−NMR(CDCl,150.9MHz)δ28.2,45.2,71.1,119.1,127.5,128.6,129.9,131.7,134.9,143.3,180.0。
IR(KBr)3024,2976,2933,1658,1597,1560,1335,1313,1254,1214,1174,1066,978,943,792,751,690,682cm−1
mp=169.5,171.5℃。
MS(EI,m/z)228(M)。
The same reaction apparatus as in Reference Example 4 was used, except that benzaldehyde was replaced with cinnamaldehyde, and the same operation as in Reference Example 4 was performed to obtain the target 1- (3-phenylpropylidene-2-ene) -5,5-dimethyl. -3-Oxopyrazolidine N, N-betaine was obtained (yellow solid, yield 99%).
1 H-NMR (CDCl 3 , 200 MHz) δ 1.65 (s, 6H), 2.75 (s, 2H), 6.92 (d, J = 9.6 Hz, 1H), 7.09 (d, J = 16.2 Hz, 1H), 7.35-7.38 (m, 3H), 7.50-7.55 (m, 2H), 7.66 (dd, J = 9.6, 16.2 Hz, 1H).
13 C-NMR (CDCl 3 , 150.9 MHz) δ 28.2, 45.2, 71.1, 119.1, 127.5, 128.6, 129.9, 131.7, 134.9, 143. 3,180.0.
IR (KBr) 3024, 2976, 2933, 1658, 1597, 1560, 1335, 1313, 1254, 1214, 1174, 1066, 978, 943, 792, 751, 690, 682 cm −1 .
mp = 169.5, 171.5 ° C.
MS (EI, m / z) 228 (M <+> ).

参考例22
1−(シクロヘキシル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタインの調製
Reference Example 22
Preparation of 1- (cyclohexyl) methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine

参考例4と同じ反応装置を用い、ベンズアルデヒドに替えてシクロヘキサンカルボアルデヒドに替えた以外、参考例4と同じ操作を行い目的物の1−(シクロヘキシル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタインを得た(白色固体、収率68%)。
H−NMR(CDCl,600MHz)δ1.22−1.40(m,5H),1.60(s,6H),1.69−1.76(m,3H),1.92−1.94(m,2H),2.69(s,2H),3.10−3.15(m,1H),6.42(d,J=7.2Hz,1H)。
13C−NMR(CDCl,150.9MHz)δ24.7,25.4,28.2,28.6,37.6,45.9,71.6,140.6,180.2。
IR(KBr)3429(br),3033,2929,2854,1668,1595,1450,1340,1285,1235,1185,1146,1112,1062,968,946,897,809,774,680cm−1
mp =94−97℃。
MS(EI,m/z)208(M)。
The same reaction apparatus as in Reference Example 4 was used, except that benzaldehyde was replaced with cyclohexanecarbaldehyde, and the same operation as in Reference Example 4 was performed to obtain the target product 1- (cyclohexyl) methylidene-5,5-dimethyl-3-oxopyra. Zolidine N, N-betaine was obtained (white solid, yield 68%).
1 H-NMR (CDCl 3 , 600 MHz) δ 1.22-1.40 (m, 5H), 1.60 (s, 6H), 1.69-1.76 (m, 3H), 1.92-1 .94 (m, 2H), 2.69 (s, 2H), 3.10-3.15 (m, 1H), 6.42 (d, J = 7.2 Hz, 1H).
13 C-NMR (CDCl 3 , 150.9 MHz) δ 24.7, 25.4, 28.2, 28.6, 37.6, 45.9, 71.6, 140.6, 180.2.
IR (KBr) 3429 (br), 3033, 2929, 2854, 1668, 1595, 1450, 1340, 1285, 1235, 1185, 1146, 1112, 1062, 968, 946, 897, 809, 774, 680 cm −1 .
mp = 94-97 ° C.
MS (EI, m / z) 208 (M <+> ).

実施例1
(S)−1−(2,2,2−トリフルオロ−1−フェニル−1−エチル)−5,5−ジメチル−3−オキソピラゾリジンの調製
Example 1
Preparation of (S) -1- (2,2,2-trifluoro-1-phenyl-1-ethyl) -5,5-dimethyl-3-oxopyrazolidine

攪拌子を備えた10mlの丸底フラスコに窒素気流下、室温条件で参考例4で調製した1−ベンジリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン1a(20.2mg,0.10mmol)、キラル相間移動触媒A(6.0mg,0.010mmol)、水酸化カリウム(33.7mg,0.60mmol,6.0equiv)及びトルエン/ジクロロメタン混合溶剤(2/1 vol/vol,1.0mL)を仕込み−50℃に冷却した後、これにトリメチルシリルトリフルオロメタン(59.1μL,0.40mmol,4.0equiv)を添加し、同温度で17時間反応を行った。反応終了後、飽和の塩化アンモニウム水溶液を添加、水層をジクロロメタンで抽出、有機層を合わせて飽和の食塩水で洗浄、硫酸ナトリウム上で乾燥、ろ過、減圧下濃縮し、粗製物を得た。得られた粗製物はシリカゲルのフラッシュ・カラムクロマトグラフィー(n−ヘキサン/酢酸エチル=1/1 vol/vol)で精製することにより目的物(S)−1−(2,2,2−トリフルオロ−1−フェニル−1−エチル)−5,5−ジメチル−3−オキソピラゾリジン1bを白色の固体として得た(25.6mg,収率94%,90%ee)。
H−NMR(CDCl,200MHz)δ1.32(s,3H),1.48(s,3H),1.62,1.77(AB quartet,J=16.1Hz,2H),4.51(q,J=8.9Hz,1H),7.35−7.42(m,3H),7.46−7.51(m,2H),7.58(brs,1H)。
13C−NMR(CDOD,150.9MHz)δ25.0,30.9,44.9,67.5(q,J=28.2Hz),67.6,127.7(q,J=280.2Hz),130.6,131.3,133.2,133.5,180.2。
19F−NMR(CDCl,188MHz)δ−70.7(d,J=9.2Hz,3F)。
IR(KBr)3186,3086,2980,2929,1694,1497,1455,1360,1275,1242,1167,1124,1088,1033,898,846,710,658cm−1
mp=191−192℃(ジクロロメタン/n−ヘキサン再結晶品)。
MS(EI,m/z)252(M)。
HRMS calcd. for C1315O:272.1136 Found:272.1138。
光学純度(ee%)の決定は、ダイセル社製キラルカラムOJ−Hにより決定した(n−ヘキサン/2−プロパノール=95/5 vol/vol,流量0.5mL/min,λ=254nm,τmaj=16.9min,τmin=21.0min)。
[α] 25=+41.1(c=0.27,MeOH),90%ee。
1-Benzylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine 1a (20.2 mg) prepared in Reference Example 4 under a room temperature condition in a 10 ml round bottom flask equipped with a stir bar , 0.10 mmol), chiral phase transfer catalyst A (6.0 mg, 0.010 mmol), potassium hydroxide (33.7 mg, 0.60 mmol, 6.0 equiv) and toluene / dichloromethane mixed solvent (2/1 vol / vol). , 1.0 mL) and cooled to −50 ° C., trimethylsilyltrifluoromethane (59.1 μL, 0.40 mmol, 4.0 equiv) was added thereto, and the reaction was performed at the same temperature for 17 hours. After completion of the reaction, a saturated aqueous ammonium chloride solution was added, the aqueous layer was extracted with dichloromethane, the organic layers were combined, washed with saturated brine, dried over sodium sulfate, filtered and concentrated under reduced pressure to obtain a crude product. The obtained crude product was purified by flash column chromatography on silica gel (n-hexane / ethyl acetate = 1/1 vol / vol) to give the desired product (S) -1- (2,2,2-trifluoro). -1-Phenyl-1-ethyl) -5,5-dimethyl-3-oxopyrazolidine 1b was obtained as a white solid (25.6 mg, 94% yield, 90% ee).
1 H-NMR (CDCl 3 , 200 MHz) δ 1.32 (s, 3H), 1.48 (s, 3H), 1.62, 1.77 (AB quartet, J = 16.1 Hz, 2H), 4. 51 (q, J = 8.9 Hz, 1H), 7.35-7.42 (m, 3H), 7.46-7.51 (m, 2H), 7.58 (brs, 1H).
13 C-NMR (CD 3 OD, 150.9 MHz) δ 25.0, 30.9, 44.9, 67.5 (q, J = 28.2 Hz), 67.6, 127.7 (q, J = 280.2 Hz), 130.6, 131.3, 133.2, 133.5, 180.2.
19 F-NMR (CDCl 3 , 188 MHz) δ-70.7 (d, J = 9.2 Hz, 3F).
IR (KBr) 3186, 3086, 2980, 2929, 1694, 1497, 1455, 1360, 1275, 1242, 1167, 1124, 1088, 1033, 898, 846, 710, 658 cm −1 .
mp = 191-192 ° C. (dichloromethane / n-hexane recrystallized product).
MS (EI, m / z) 252 (M <+> ).
HRMS calcd. for C 13 H 15 F 3 N 2 O: 272.1136 Found: 272.1138.
The optical purity (ee%) was determined by a chiral column OJ-H manufactured by Daicel (n-hexane / 2-propanol = 95/5 vol / vol, flow rate 0.5 mL / min, λ = 254 nm, τ maj = 16.9 min , τ min = 21.0 min ).
[Α] D 25 = + 41.1 (c = 0.27, MeOH), 90% ee.

実施例2
(S)−1−[2,2,2−トリフルオロ−1−(2−ナフト)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジンの調製
Example 2
Preparation of (S) -1- [2,2,2-trifluoro-1- (2-naphtho) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine

実施例1と同じ反応装置を用い、参考例7で調製した1−(2−ナフチル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン2a(25.2mg,0.10mmol)、キラル相間移動触媒B(5.8mg,0.010mmol)を用い、−50℃で5時間反応を行った以外、実施例1と同じ操作を行い目的物の(S)−1−[2,2,2−トリフルオロ−1−(2−ナフト)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン2b(30.6mg,95%,90%ee)を白色固体として得た。
H−NMR(CDCl,200MHz)δ1.34(s,3H),1.53(s,3H),1.62,1.76(AB quartet,J=16.0Hz,2H),4.68(q,J=8.7Hz,1H),7.49−7.60(m,4H),7.81−7.88(m,3H),7.96(s,1H)。
13C−NMR(CDOD,150.9MHz)δ25.1,30.8,45.0,67.6(q,J=28.2Hz),67.7,127.8(q,J=280.2Hz),128.6,129.2,129.6,129.9,130.1,130.3,130.6,131.0,133.3,135.4,135.7,180.2。
19F NMR(CDCl,188MHz)δ−70.4(d,J=7.9Hz,3F)。
IR(KBr)3176,3067,2985,2925,2855,1698,1598,1508,1418,1358,1272,1167,1122,1041,919,832,763,712,680cm−1
mp=204−205.5℃(ジクロロメタン/n−ヘキサン再結晶品)。
MS(EI,m/z)322(M)。
HRMS calcd. for C1717O:322.1293 Found:322.1302。
光学純度(ee%)は、ダイセル社製キラルカラムOJ−Hにより決定した(n−ヘキサン/2−プロパノール=90/10 vol/vol,流量1.0 mL/min,λ=254nm,τmaj=12.1min,τmin=8.0min)。
[α] 25=+40.7(c=0.79,MeOH),90%ee。
Using the same reaction apparatus as in Example 1, 1- (2-naphthyl) methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine 2a (25.2 mg, 0. 2) prepared in Reference Example 7 was used. 10 mmol) and chiral phase transfer catalyst B (5.8 mg, 0.010 mmol), and the same operation as in Example 1 was performed except that the reaction was performed at −50 ° C. for 5 hours. 2,2,2-trifluoro-1- (2-naphtho) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine 2b (30.6 mg, 95%, 90% ee) as a white solid Got as.
1 H-NMR (CDCl 3 , 200 MHz) δ 1.34 (s, 3H), 1.53 (s, 3H), 1.62, 1.76 (AB quartet, J = 16.0 Hz, 2H), 4. 68 (q, J = 8.7 Hz, 1H), 7.49-7.60 (m, 4H), 7.81-7.88 (m, 3H), 7.96 (s, 1H).
13 C-NMR (CD 3 OD, 150.9 MHz) δ 25.1, 30.8, 45.0, 67.6 (q, J = 28.2 Hz), 67.7, 127.8 (q, J = 280.2 Hz), 128.6, 129.2, 129.6, 129.9, 130.1, 130.3, 130.6, 131.0, 133.3, 135.4, 135.7, 180 .2.
19 F NMR (CDCl 3 , 188 MHz) δ-70.4 (d, J = 7.9 Hz, 3F).
IR (KBr) 3176, 3067, 2985, 2925, 2855, 1698, 1598, 1508, 1418, 1358, 1272, 1167, 1122, 1041, 919, 832, 763, 712, 680 cm −1 .
mp = 204-205.5 [deg.] C. (dichloromethane / n-hexane recrystallized product).
MS (EI, m / z) 322 (M <+> ).
HRMS calcd. for C 17 H 17 F 3 N 2 O: 322.1293 Found: 322.1302.
The optical purity (ee%) was determined by a chiral column OJ-H manufactured by Daicel (n-hexane / 2-propanol = 90/10 vol / vol, flow rate 1.0 mL / min, λ = 254 nm, τ maj = 12). .1 min , τ min = 8.0 min ).
[Α] D 25 = + 40.7 (c = 0.79, MeOH), 90% ee.

実施例3
(S)−1−[2,2,2−トリフルオロ−1−(2−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジンの調製
Example 3
Preparation of (S) -1- [2,2,2-trifluoro-1- (2-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine

実施例1と同じ反応装置を用い、参考例8で調製した1−(6−メトキシ−2−ナフチル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン3a(28.2 mg,0.10mmol)、キラル相間移動触媒A(18.0mg,0.030mmol)を用い、−40℃で8時間反応を行った以外、実施例1と同じ操作を行い目的物の(S)−1−[2,2,2−トリフルオロ−1−(2−ナフト)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン3b(31.7mg,90%,90%ee)を白色固体として得た。
H−NMR(CDCl,200MHz)δ1.34(s,3H),1.53(s,3H),1.62,1.74(AB quartet,J=15.3Hz,2H),3.92(s,3H),4.64(q,J=8.9Hz,1H),7.11−7.20(m,2H),7.36(s,1H),7.54(d,J=8.4Hz,1H),7.74(d,J=7.8Hz,2H),7.86(s,1H)。
13C−NMR(CDOD,150.9MHz)δ25.1,30.9,45.0,56.8,67.6(q,J=28.2Hz),67.6,107.4,121.5,127.9(q,J=280.2Hz),128.4,129.0,130.4,130.9,131.8,133.0,137.2,161.1,180.3。
19F−NMR(CDCl,188MHz)δ−70.4(d,J=9.2Hz,3F)。
IR(KBr)3210,3064,2975,2848,2416,1696,1634,1607,1486,1400,1346,1276,1223,1152,1114,1033,853cm−1
mp=205−206.5℃(ジクロロメタン/n−ヘキサン再結晶品)。
MS(EI,m/z)352(M)。
HRMS calcd. for C1819:352.1399 Found:352.1387。
光学純度(ee%)は、ダイセル社製キラルカラムOD−Hにより決定した(n−ヘキサン/2−プロパノール=95/5 vol/vol,流量0.5mL/min,λ=254nm,τmaj=31.5min,τmin=24.5min)。
[α] 25=+44.3(c=0.37,MeOH),90%ee。
Using the same reaction apparatus as in Example 1, 1- (6-methoxy-2-naphthyl) methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine 3a (28. 2 mg, 0.10 mmol) and chiral phase transfer catalyst A (18.0 mg, 0.030 mmol), except that the reaction was carried out at −40 ° C. for 8 hours. ) -1- [2,2,2-trifluoro-1- (2-naphtho) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine 3b (31.7 mg, 90%, 90%) ee) was obtained as a white solid.
1 H-NMR (CDCl 3 , 200 MHz) δ 1.34 (s, 3H), 1.53 (s, 3H), 1.62, 1.74 (AB quartet, J = 15.3 Hz, 2H), 3. 92 (s, 3H), 4.64 (q, J = 8.9 Hz, 1H), 7.11-7.20 (m, 2H), 7.36 (s, 1H), 7.54 (d, J = 8.4 Hz, 1H), 7.74 (d, J = 7.8 Hz, 2H), 7.86 (s, 1H).
13 C-NMR (CD 3 OD, 150.9 MHz) δ 25.1, 30.9, 45.0, 56.8, 67.6 (q, J = 28.2 Hz), 67.6, 107.4 121.5, 127.9 (q, J = 280.2 Hz), 128.4, 129.0, 130.4, 130.9, 131.8, 133.0, 137.2, 161.1, 180 .3.
19 F-NMR (CDCl 3 , 188 MHz) δ-70.4 (d, J = 9.2 Hz, 3F).
IR (KBr) 3210, 3064, 2975, 2848, 2416, 1696, 1634, 1607, 1486, 1400, 1346, 1276, 1223, 1152, 1114, 1033, 853 cm −1 .
mp = 205-206.5 ° C. (dichloromethane / n-hexane recrystallized product).
MS (EI, m / z) 352 (M <+> ).
HRMS calcd. for C 18 H 19 F 3 N 2 O 2: 352.1399 Found: 352.1387.
The optical purity (ee%) was determined by a chiral column OD-H manufactured by Daicel (n-hexane / 2-propanol = 95/5 vol / vol, flow rate 0.5 mL / min, λ = 254 nm, τ maj = 31. 5 min, τ min = 24.5 min ).
[Α] D 25 = + 44.3 (c = 0.37, MeOH), 90% ee.

実施例4
(S)−1−[2,2,2−トリフルオロ−1−(1−ナフチル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジンの調製
Example 4
Preparation of (S) -1- [2,2,2-trifluoro-1- (1-naphthyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine

実施例1と同じ反応装置を用い、参考例9で調製した1−(1−ナフト)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン4a(25.2mg,0.10mmol)、キラル相間移動触媒B(5.8mg,0.010mmol)を用い、−50〜−40℃で18時間反応を行った以外、実施例1と同じ操作を行い目的物の(S)−1−[2,2,2−トリフルオロ−1−(1−ナフト)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン4b(23.7mg,74%,93%ee)を白色固体として得た。
H−NMR(CDCl,200MHz)δ1.21(s,3H),1.25(s,3H),1.65,1.98(AB quartet,J=16.2Hz,2H),5.40(q,J=8.3Hz,1H),7.20(s,1H),7.45−7.64(m,3H),7.90(d,J=8.2Hz,2H),8.02(t,J=6.6Hz,2H)。
13C−NMR(DMSO,150.9MHz)δ25.8,27.4,42.8,58.8−59.0(m),65.7,123.9,125.4,125.7(q,J=281.2Hz),126.3,127.4,128.4,129.5,129.7,130.0,131.8,134.0,176.5。
19F−NMR(CDCl,188MHz)δ−69.3(d,J=7.9Hz,3F)。
IR(KBr)3147,3058,2846,1708,1671,1413,1350,1271,1158,1126,1033,1003,896,849,782,679cm−1
mp=233−234℃(ジクロロメタン/n−ヘキサン再結晶品)。
MS(EI,m/z)322(M)。
HRMS calcd. for C1717O:322.1293 Found:322.1284。
光学純度(ee%)は、ダイセル社製キラルカラムOJ−Hにより決定した(n−ヘキサン/2−プロパノール=95/5 vol/vol,流量0.5L/min,λ=254nm,τmaj=41.5min,τmin=21.4min)。
[α] 25=−116.5(c=0.52,MeOH),93%ee。
Using the same reactor as in Example 1, 1- (1-naphtho) methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine 4a (25.2 mg, 0. 2) prepared in Reference Example 9 was used. 10 mmol) and chiral phase transfer catalyst B (5.8 mg, 0.010 mmol), and the same operation as in Example 1 was performed except that the reaction was performed at −50 to −40 ° C. for 18 hours. 1- [2,2,2-trifluoro-1- (1-naphth) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine 4b (23.7 mg, 74%, 93% ee) Was obtained as a white solid.
1 H-NMR (CDCl 3 , 200 MHz) δ 1.21 (s, 3H), 1.25 (s, 3H), 1.65, 1.98 (AB quartet, J = 16.2 Hz, 2H), 5. 40 (q, J = 8.3 Hz, 1H), 7.20 (s, 1H), 7.45-7.64 (m, 3H), 7.90 (d, J = 8.2 Hz, 2H), 8.02 (t, J = 6.6 Hz, 2H).
13 C-NMR (DMSO, 150.9 MHz) δ 25.8, 27.4, 42.8, 58.8-59.0 (m), 65.7, 123.9, 125.4, 125.7 ( q, J = 281.2 Hz), 126.3, 127.4, 128.4, 129.5, 129.7, 130.0, 131.8, 134.0, 176.5.
19 F-NMR (CDCl 3 , 188 MHz) δ-69.3 (d, J = 7.9 Hz, 3F).
IR (KBr) 3147, 3058, 2846, 1708, 1671, 1413, 1350, 1271, 1158, 1126, 1033, 1003, 896, 849, 782, 679 cm −1 .
mp = 233-234 ° C. (dichloromethane / n-hexane recrystallized product).
MS (EI, m / z) 322 (M <+> ).
HRMS calcd. for C 17 H 17 F 3 N 2 O: 322.1293 Found: 322.1284.
The optical purity (ee%) was determined by a chiral column OJ-H manufactured by Daicel (n-hexane / 2-propanol = 95/5 vol / vol, flow rate 0.5 L / min, λ = 254 nm, τ maj = 41. 5 min, τ min = 21.4 min ).
[Α] D 25 = −116.5 (c = 0.52, MeOH), 93% ee.

実施例5
(S)−1−[2,2,2−トリフルオロ−1−(2−メチルフェニル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジンの調製
Example 5
Preparation of (S) -1- [2,2,2-trifluoro-1- (2-methylphenyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine

実施例1と同じ反応装置を用い、参考例10で調製した1−(2−メチルフェニル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン5a(21.6mg,0.10mmol)、キラル相間移動触媒A(6.0mg,0.010mmol)を用い、−50〜−40℃で20時間反応を行った以外、実施例1と同じ操作を行い目的物の(S)−1−[2,2,2−トリフルオロ−1−(2−メチルフェニル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン5b(24.6mg,86%,88%ee)を白色固体として得た。
H−NMR(CDCl,200MHz)δ1.21(s,3H),1.27(s,3H),1.94,2.15(ABquartet,J=16.1Hz,2H),2.41(s,3H),4.70(q,J=8.1Hz,1H),7.16−7.31(m,4H),7.78−7.81(m,1H)。
13C−NMR(CDOD,150.9MHz)δ21.1,26.8,28.5,44.9,63.3(q,J=27.2Hz),67.6,127.6(q,J=280.7Hz),128.1,131.1,131.3,133.3,134.3,139.5,179.8。
19F−NMR(CDCl,188MHz)δ−69.1(d,J=7.9Hz,3F)。
IR(KBr)3153,3067,2989,2849,1701,1674,1602,1473,1355,1266,1215,1160,1130,1042,929,894,735,654cm−1
mp = 191.5−193℃(ジクロロメタン/n−ヘキサン再結晶品)。
MS(EI,m/z)286(M)。
HRMS calcd. for C1417O:286.1293 Found:286.1289。
光学純度(ee%)は、ダイセル社製キラルカラムOD−Hにより決定した(n−ヘキサン/2−プロパノール=98/2 vol/vol,流量0.5mL/min,λ= 254nm,τmaj=30.7min,τmin=33.9min)。
[α] 25=−8.3(c=0.64,MeOH),88%ee。
Using the same reaction apparatus as in Example 1, 1- (2-methylphenyl) methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine 5a (21.6 mg, 0) prepared in Reference Example 10 was used. .10 mmol) and chiral phase transfer catalyst A (6.0 mg, 0.010 mmol), and the same operation as in Example 1 was performed except that the reaction was performed at −50 to −40 ° C. for 20 hours. -1- [2,2,2-trifluoro-1- (2-methylphenyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine 5b (24.6 mg, 86%, 88% ee) was obtained as a white solid.
1 H-NMR (CDCl 3 , 200 MHz) δ 1.21 (s, 3H), 1.27 (s, 3H), 1.94, 2.15 (ABquartet, J = 16.1 Hz, 2H), 2.41 (S, 3H), 4.70 (q, J = 8.1 Hz, 1H), 7.16-7.31 (m, 4H), 7.78-7.81 (m, 1H).
13 C-NMR (CD 3 OD, 150.9 MHz) δ21.1, 26.8, 28.5, 44.9, 63.3 (q, J = 27.2 Hz), 67.6, 127.6 ( q, J = 280.7 Hz), 128.1, 131.1, 131.3, 133.3, 134.3, 139.5, 179.8.
19 F-NMR (CDCl 3 , 188 MHz) δ-69.1 (d, J = 7.9 Hz, 3F).
IR (KBr) 3153, 3067, 2989, 2849, 1701, 1674, 1602, 1473, 1355, 1266, 1215, 1160, 1130, 1042, 929, 894, 735, 654 cm −1 .
mp = 191.5-193 ° C. (dichloromethane / n-hexane recrystallized product).
MS (EI, m / z) 286 (M <+> ).
HRMS calcd. for C 14 H 17 F 3 N 2 O: 286.1293 Found: 286.1289.
The optical purity (ee%) was determined by a chiral column OD-H manufactured by Daicel (n-hexane / 2-propanol = 98/2 vol / vol, flow rate 0.5 mL / min, λ = 254 nm, τ maj = 30. 7 min , τ min = 33.9 min ).
[Α] D 25 = -8.3 ( c = 0.64, MeOH), 88% ee.

実施例6
(S)−1−[2,2,2−トリフルオロ−1−(3−メチルフェニル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジンの調製
Example 6
Preparation of (S) -1- [2,2,2-trifluoro-1- (3-methylphenyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine

実施例1と同じ反応装置を用い、参考例11で調製した1−(3−メチルフェニル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン6a(21.6mg,0.10mmol)、キラル相間移動触媒B(5.8mg,0.010mmol)を用い、−50℃で6時間反応を行った以外、実施例1と同じ操作を行い目的物の(S)−1−[2,2,2−トリフルオロ−1−(3−メチルフェニル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン6b(20.6mg,72%,94%ee)を白色固体として得た。
H−NMR(CDCl,200MHz)δ1.32(s,3H),1.46(s,3H),1.65,1.77(AB quartet,J=15.8Hz,2H),2.36(s,3H),4.46(q,J=8.8Hz,1H),7.21−7.30(m,5H)。
13C NMR(DMSO,150.9MHz)δ21.5,24.1,29.5,43.2,64.5(q,J=27.2Hz),65.3,125.8(q,J=280.7Hz),128.4,128.5,130.0,131.8,132.0,137.8,176.2。
19F−NMR(CDCl,188MHz)δ−70.6(d,J=9.2Hz,3F)。
IR(KBr)3189,3076,2983,2927,1703,1605,1494,1417,1356,1275,1156,1125,1034,1000,944,822,788,719cm−1
mp=198−201℃(ジクロロメタン/n−ヘキサン再結晶品)。
MS(EI,m/z)286(M)。
HRMS calcd. for C1417O:286.1293 Found:286.1282。
光学純度(ee%)は、ダイセル社製キラルカラムOD−Hにより決定した(n−ヘキサン/2−プロパノール=98/2 vol/vol,流量0.5mL/min,λ=254nm,τmaj=24.4 min,τmin=26.4min)。
[α] 25=+42.4(c=0.64,MeOH),94%ee。
Using the same reactor as in Example 1, 1- (3-methylphenyl) methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine 6a (21.6 mg, 0) prepared in Reference Example 11 was used. .10 mmol) and chiral phase transfer catalyst B (5.8 mg, 0.010 mmol), and the same operation as in Example 1 was conducted except that the reaction was performed at −50 ° C. for 6 hours. [2,2,2-trifluoro-1- (3-methylphenyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine 6b (20.6 mg, 72%, 94% ee) Obtained as a white solid.
1 H-NMR (CDCl 3 , 200 MHz) δ 1.32 (s, 3H), 1.46 (s, 3H), 1.65, 1.77 (AB quartet, J = 15.8 Hz, 2H), 2. 36 (s, 3H), 4.46 (q, J = 8.8 Hz, 1H), 7.21-7.30 (m, 5H).
13 C NMR (DMSO, 150.9 MHz) δ 21.5, 24.1, 29.5, 43.2, 64.5 (q, J = 27.2 Hz), 65.3, 125.8 (q, J = 280.7 Hz), 128.4, 128.5, 130.0, 131.8, 132.0, 137.8, 176.2.
19 F-NMR (CDCl 3 , 188 MHz) δ-70.6 (d, J = 9.2 Hz, 3F).
IR (KBr) 3189, 3076, 2983, 2927, 1703, 1605, 1494, 1417, 1356, 1275, 1156, 1125, 1034, 1000, 944, 822, 788, 719 cm- 1 .
mp = 198-201 ° C. (dichloromethane / n-hexane recrystallized product).
MS (EI, m / z) 286 (M <+> ).
HRMS calcd. for C 14 H 17 F 3 N 2 O: 286.1293 Found: 286.1282.
The optical purity (ee%) was determined by a chiral column OD-H manufactured by Daicel (n-hexane / 2-propanol = 98/2 vol / vol, flow rate 0.5 mL / min, λ = 254 nm, τ maj = 24. 4 min, τ min = 26.4 min ).
[Α] D 25 = + 42.4 (c = 0.64, MeOH), 94% ee.

実施例7
(S)−1−[2,2,2−トリフルオロ−1−(4−メチルフェニル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジンの調製
Example 7
Preparation of (S) -1- [2,2,2-trifluoro-1- (4-methylphenyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine

実施例1と同じ反応装置を用い、参考例12で調製した1−(4−メチルフェニル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン7a(21.6mg,0.10mmol)、キラル相間移動触媒B(5.8mg,0.010mmol)を用い、−50℃で8時間反応を行った以外、実施例1と同じ操作を行い目的物の(S)−1−[2,2,2−トリフルオロ−1−(4−メチルフェニル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン7b(25.0mg,87%,90%ee)を白色固体として得た。
H−NMR(CDCl,200MHz)δ1.32(s,3H),1.47(s,3H),1.64,1.75(ABquartet,J=15.8Hz,2H),2.35(s,3H),4.47(q,J=8.9Hz),7.18(d,J=8.2Hz,2H),7.28(s,1H),7.35(d,J=8.2Hz,2H)。
13C−NMR(CDOD,150.9MHz)δ22.2,24.9,30.9,44.9,67.3(q,J=28.2Hz),67.5,127.7(q,J=279.7Hz),130.4,131.2,133.1,141.5,180.2。
19F−NMR(CDCl,188MHz)δ−70.7(d,J=7.9Hz,3F)。
IR(KBr)3184,3077,2970,1693,1512,1420,1377,1363,1270,1174,1126,1036,1005,900,821,733,648cm−1
mp=179−180℃(ジクロロメタン/n−ヘキサン再結晶品)。
MS(EI,m/z)286(M)。
HRMS calcd. for C1417O:286.1293 Found:286.1304。
光学純度(ee%)は、ダイセル社製キラルカラムAD−Hにより決定した(n−ヘキサン/2−プロパノール=95/5 vol/vol,流量0.5mL/min,λ=254nm,τmaj=16.3min,τmin=17.4min)。
[α] 25=+39.0(c=0.49,MeOH),90%ee。
Using the same reaction apparatus as in Example 1, 1- (4-methylphenyl) methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine 7a (21.6 mg, 0) prepared in Reference Example 12 was used. .10 mmol) and chiral phase transfer catalyst B (5.8 mg, 0.010 mmol), and the same operation as in Example 1 was performed except that the reaction was performed at −50 ° C. for 8 hours. [2,2,2-trifluoro-1- (4-methylphenyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine 7b (25.0 mg, 87%, 90% ee) Obtained as a white solid.
1 H-NMR (CDCl 3 , 200 MHz) δ 1.32 (s, 3H), 1.47 (s, 3H), 1.64, 1.75 (ABquartet, J = 15.8 Hz, 2H), 2.35 (S, 3H), 4.47 (q, J = 8.9 Hz), 7.18 (d, J = 8.2 Hz, 2H), 7.28 (s, 1H), 7.35 (d, J = 8.2 Hz, 2H).
13 C-NMR (CD 3 OD, 150.9 MHz) δ 22.2, 24.9, 30.9, 44.9, 67.3 (q, J = 28.2 Hz), 67.5, 127.7 ( q, J = 279.7 Hz), 130.4, 131.2, 133.1, 141.5, 180.2.
19 F-NMR (CDCl 3 , 188 MHz) δ-70.7 (d, J = 7.9 Hz, 3F).
IR (KBr) 3184, 3077, 2970, 1693, 1512, 1420, 1377, 1363, 1270, 1174, 1126, 1036, 1005, 900, 821, 733, 648 cm −1 .
mp = 179-180 ° C. (dichloromethane / n-hexane recrystallized product).
MS (EI, m / z) 286 (M <+> ).
HRMS calcd. for C 14 H 17 F 3 N 2 O: 286.1293 Found: 286.1304.
The optical purity (ee%) was determined by a chiral column AD-H manufactured by Daicel (n-hexane / 2-propanol = 95/5 vol / vol, flow rate 0.5 mL / min, λ = 254 nm, τ maj = 16. 3 min, τ min = 17.4 min ).
[Α] D 25 = + 39.0 (c = 0.49, MeOH), 90% ee.

実施例8
(S)−1−[2,2,2−トリフルオロ−1−(3−メトキシフェニル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジンの調製
Example 8
Preparation of (S) -1- [2,2,2-trifluoro-1- (3-methoxyphenyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine

実施例1と同じ反応装置を用い、参考例13で調製した1−(3−メトキシフェニル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン8a(23.2mg,0.10mmol)、キラル相間移動触媒B(5.8mg,0.010mmol)を用い、−50℃で3時間反応を行った以外、実施例1と同じ操作を行い目的物の(S)−1−[2,2,2−トリフルオロ−1−(3−メトキシフェニル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン8b(22.1mg,73%,92%ee)を白色固体として得た。
H−NMR(CDCl,200MHz)δ1.32(s,3H),1.48(s,3H),1.71,1.79(ABquartet,J=16.0Hz,2H),3.79(s,3H),4.46(q,J=8.7Hz),6.90−6.96(m,1H),7.02−7.05(m,2H),7.25−7.34(m,1H),7.38−7.56(br,1H)。
13C−NMR(CDOD,150.9MHz)δ25.0,30.8,45.0,56.8,67.4(q,J=27.9Hz),67.6,116.9,118.8,125.6,127.7(q,J=279.7Hz),131.6,134.9,162.0,180.3。
19F−NMR(CDCl,188MHz)δ−70.6(d,J=9.2Hz,3F)。
IR(KBr)3186,3077,2979,2947,1701,1583,1494,1358,1297,1274,1247,1154,1119,1064,947,773,721cm−1
mp=183−184 oC(ジクロロメタン/n−ヘキサン再結晶品)。
MS(EI,m/z)302(M)。
HRMS calcd. for C1417:302.1242 Found:302.1269。
光学純度(ee%)は、ダイセル社製キラルカラムOD−Hにより決定した(n−ヘキサン/2−プロパノール=95/5 vol/vol,流量1.0mL/min,λ=254nm,τmaj=8.9min,τmin=12.1min)。
[α] 25=+52.0(c=0.49,MeOH),92%ee。
Using the same reaction apparatus as in Example 1, 1- (3-methoxyphenyl) methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine 8a (23.2 mg, 0) prepared in Reference Example 13 was used. .10 mmol), chiral phase transfer catalyst B (5.8 mg, 0.010 mmol), and the same operation as in Example 1 was performed except that the reaction was performed at −50 ° C. for 3 hours. [2,2,2-trifluoro-1- (3-methoxyphenyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine 8b (22.1 mg, 73%, 92% ee). Obtained as a white solid.
1 H-NMR (CDCl 3 , 200 MHz) δ 1.32 (s, 3H), 1.48 (s, 3H), 1.71, 1.79 (ABquartet, J = 16.0 Hz, 2H), 3.79 (S, 3H), 4.46 (q, J = 8.7 Hz), 6.90-6.96 (m, 1H), 7.02-7.05 (m, 2H), 7.25-7 .34 (m, 1H), 7.38-7.56 (br, 1H).
13 C-NMR (CD 3 OD, 150.9 MHz) δ 25.0, 30.8, 45.0, 56.8, 67.4 (q, J = 27.9 Hz), 67.6, 116.9, 118.8, 125.6, 127.7 (q, J = 279.7 Hz), 131.6, 134.9, 162.0, 180.3.
19 F-NMR (CDCl 3 , 188 MHz) δ-70.6 (d, J = 9.2 Hz, 3F).
IR (KBr) 3186, 3077, 2979, 2947, 1701, 1583, 1494, 1358, 1297, 1274, 1247, 1154, 1119, 1064, 947, 773, 721 cm −1 .
mp = 183-184 oC (dichloromethane / n-hexane recrystallized product).
MS (EI, m / z) 302 (M <+> ).
HRMS calcd. for C 14 H 17 F 3 N 2 O 2: 302.1242 Found: 302.1269.
The optical purity (ee%) was determined by a chiral column OD-H manufactured by Daicel (n-hexane / 2-propanol = 95/5 vol / vol, flow rate 1.0 mL / min, λ = 254 nm, τ maj = 8. 9 min , τ min = 12.1 min ).
[Α] D 25 = + 52.0 (c = 0.49, MeOH), 92% ee.

実施例9
(S)−1−[2,2,2−トリフルオロ−1−(4−メトキシフェニル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジンの調製
Example 9
Preparation of (S) -1- [2,2,2-trifluoro-1- (4-methoxyphenyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine

実施例1と同じ反応装置を用い、参考例14で調製した1−(4−メトキシフェニル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン9a(23.2mg,0.10mmol)、キラル相間移動触媒B(5.8mg,0.010mmol)を用い、−50℃で8時間反応を行った以外、実施例1と同じ操作を行い目的物の(S)−1−[2,2,2−トリフルオロ−1−(4−メトキシフェニル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン9b(25.3mg,84%,95%ee)を白色固体として得た。
H−NMR(CDCl,200MHz)δ1.32(s,3H),1.47(s,3H),1.65,1.76(ABquartet,J=16.1Hz,2H),3.80(s,3H),4.46(q,J=8.9Hz,1H),6.86−6.94(m,2H),7.34(brs,1H),7.39(d,J=8.8Hz,2H)。
13C−NMR(CDOD,150.9MHz)δ24.9,30.9,44.9,56.7,66.9(q,J=28.2Hz),67.4,116.0,125.1,127.8(q,J=280.2Hz),134.4,162.8,180.3。
19F−NMR(CDCl,188MHz)δ−70.9(d,J=9.0Hz,3F)。
IR(KBr)3155,3059,2970,2841,1697,1610,1516,1471,1356,1308,1273,1252,1172,1111,1037,987,826cm−1
mp=135−136.5℃(ジクロロメタン/n−ヘキサン再結晶品)。
MS(EI,m/z)302(M)。
HRMS calcd. for C1417:302.1242 Found:302.1220。
光学純度(ee%)は、ダイセル社製キラルカラムAD−Hにより決定した(n−ヘキサン/2−プロパノール=95/5 vol/vol,流量0.5mL/min,λ=254nm,τmaj=24.8min,τmin=26.4min)。
[α] 25=+40.7(c=0.49,MeOH),95%ee。
Using the same reactor as in Example 1, 1- (4-methoxyphenyl) methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine 9a (23.2 mg, 0) prepared in Reference Example 14 was used. .10 mmol) and chiral phase transfer catalyst B (5.8 mg, 0.010 mmol), and the same operation as in Example 1 was performed except that the reaction was performed at −50 ° C. for 8 hours. [2,2,2-trifluoro-1- (4-methoxyphenyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine 9b (25.3 mg, 84%, 95% ee). Obtained as a white solid.
1 H-NMR (CDCl 3 , 200 MHz) δ 1.32 (s, 3H), 1.47 (s, 3H), 1.65, 1.76 (ABquartet, J = 16.1 Hz, 2H), 3.80 (S, 3H), 4.46 (q, J = 8.9 Hz, 1H), 6.86-6.94 (m, 2H), 7.34 (brs, 1H), 7.39 (d, J = 8.8 Hz, 2H).
13 C-NMR (CD 3 OD, 150.9 MHz) δ 24.9, 30.9, 44.9, 56.7, 66.9 (q, J = 28.2 Hz), 67.4, 116.0, 125.1, 127.8 (q, J = 280.2 Hz), 134.4, 162.8, 180.3.
19 F-NMR (CDCl 3 , 188 MHz) δ-70.9 (d, J = 9.0 Hz, 3F).
IR (KBr) 3155, 3059, 2970, 2841, 1697, 1610, 1516, 1471, 1356, 1308, 1273, 1252, 1172, 1111, 1037, 987, 826 cm −1 .
mp = 135-136.5 ° C. (dichloromethane / n-hexane recrystallized product).
MS (EI, m / z) 302 (M <+> ).
HRMS calcd. for C 14 H 17 F 3 N 2 O 2: 302.1242 Found: 302.1220.
The optical purity (ee%) was determined by a chiral column AD-H manufactured by Daicel (n-hexane / 2-propanol = 95/5 vol / vol, flow rate 0.5 mL / min, λ = 254 nm, τ maj = 24. 8 min, τ min = 26.4 min ).
[Α] D 25 = + 40.7 (c = 0.49, MeOH), 95% ee.

実施例10
(S)−1−[2,2,2−トリフルオロ−1−(4−iso−プロピルフェニル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジンの調製
Example 10
Preparation of (S) -1- [2,2,2-trifluoro-1- (4-iso-propylphenyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine

実施例1と同じ反応装置を用い、参考例15で調製した1−(4−iso−プロピルフェニル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン10a(24.4mg,0.10mmol)、キラル相間移動触媒B(5.8mg,0.010mmol)を用い、−50℃で6時間反応を行った以外、実施例1と同じ操作を行い目的物の(S)−1−[2,2,2−トリフルオロ−1−(4−iso−プロピルフェニル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン10b(26.3mg,84%,96%ee)を白色固体として得た。
H−NMR(CDCl,200MHz)δ1.24(d,J=6.8Hz,6H),1.32(s,3H),1.47(s,3H),1.63,1.75(ABquartet,J=15.9Hz,2H),2.90(sept,J=6.9Hz,1H),4.47(q,J=8.8Hz,1H),7.22(d,J=9.0Hz,2H),7.28(brs,1H),7.88(d,J=8.2Hz,2H)。
13C−NMR(CDOD,150.9MHz)δ24.9,25.3,30.9,36.0,44.9,67.3(q,J=28.2Hz),67.5,127.7(q,J=280.2Hz),128.6,130.8,133.2,152.4,180.2。
19F−NMR(CDCl,188MHz)δ−70.7(d,J=9.2Hz,3F)。
IR(KBr)3206,3080,2971,1706,1614,1516,1462,1419,1357,1276,1159,1128,1035,902,830,748,665cm−1
mp=113−116℃(ジクロロメタン/n−ヘキサン再結晶品)。
MS(EI,m/z)314(M)。
HRMS calcd. for C1621O:314.1606 Found:314.1608。
光学純度(ee%)は、ダイセル社製キラルカラムAD−Hにより決定した(n−ヘキサン/2−プロパノール=95/5 vol/vol,流量1.0mL/min,λ=254nm,τmaj=6.7min,τmin=9.2min)。
[α] 25=+40.4(c=0.53,MeOH),96%ee。
Using the same reactor as in Example 1, 1- (4-iso-propylphenyl) methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine 10a (24.4 mg) prepared in Reference Example 15 was used. , 0.10 mmol) and chiral phase transfer catalyst B (5.8 mg, 0.010 mmol), and the same operation as in Example 1 was performed except that the reaction was performed at −50 ° C. for 6 hours. 1- [2,2,2-trifluoro-1- (4-iso-propylphenyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine 10b (26.3 mg, 84%, 96 % Ee) was obtained as a white solid.
1 H-NMR (CDCl 3 , 200 MHz) δ 1.24 (d, J = 6.8 Hz, 6H), 1.32 (s, 3H), 1.47 (s, 3H), 1.63, 1.75 (ABquartet, J = 15.9 Hz, 2H), 2.90 (sept, J = 6.9 Hz, 1H), 4.47 (q, J = 8.8 Hz, 1H), 7.22 (d, J = 9.0 Hz, 2H), 7.28 (brs, 1H), 7.88 (d, J = 8.2 Hz, 2H).
13 C-NMR (CD 3 OD, 150.9 MHz) δ 24.9, 25.3, 30.9, 36.0, 44.9, 67.3 (q, J = 28.2 Hz), 67.5, 127.7 (q, J = 280.2 Hz), 128.6, 130.8, 133.2, 152.4, 180.2.
19 F-NMR (CDCl 3 , 188 MHz) δ-70.7 (d, J = 9.2 Hz, 3F).
IR (KBr) 3206, 3080, 2971, 1706, 1614, 1516, 1462, 1419, 1357, 1276, 1159, 1128, 1035, 902, 830, 748, 665 cm −1 .
mp = 113-116 ° C. (dichloromethane / n-hexane recrystallized product).
MS (EI, m / z) 314 (M <+> ).
HRMS calcd. for C 16 H 21 F 3 N 2 O: 314.1606 Found: 314.1608.
The optical purity (ee%) was determined by a chiral column AD-H manufactured by Daicel (n-hexane / 2-propanol = 95/5 vol / vol, flow rate 1.0 mL / min, λ = 254 nm, τ maj = 6. 7 min , τ min = 9.2 min ).
[Α] D 25 = + 40.4 (c = 0.53, MeOH), 96% ee.

実施例11
(S)−1−[2,2,2−トリフルオロ−1−(4−tert−ブチルフェニル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジンの調製
Example 11
Preparation of (S) -1- [2,2,2-trifluoro-1- (4-tert-butylphenyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine

実施例1と同じ反応装置を用い、参考例16で調製した1−(4−tert−ブチルフェニル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン11a(25.8mg,0.10mmol)、キラル相間移動触媒B(5.8mg,0.010mmol)を用い、−50℃で3時間反応を行った以外、実施例1と同じ操作を行い目的物の(S)−1−[2,2,2−トリフルオロ−1−(4−tert−ブチルフェニル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン11b(29.0mg,88%,98%ee)を白色固体として得た。
H NMR(CDCl,200MHz)δ1.30(s,9H),1.32(s,3H),1.47(s,3H),1.64,1.76(ABquartet,J=15.9Hz,2H),4.47(q,J=8.9Hz,1H),7.38(s,5H)。
13C−NMR(CDOD,150.9MHz)δ24.9,30.9,32.7,36.4,44.9,67.2(q,J=28.2Hz),67.4,127.5,127.7(q,J=280.2Hz),130.4,132.9,154.6,180.2。
19F NMR(CDCl,188MHz)δ−70.7(d,J=9.2Hz,3F)。
IR(KBr)3187,3080,2973,1700,1508,1458,1419,1355,1274,1167,1120,1034,900,829,667cm−1
mp=158.5−159.5 ℃(ジクロロメタン/n−ヘキサン再結晶品)。
MS(EI,m/z)328(M)。
HRMS calcd. for C1723O:328.1762 Found:328.1771。
光学純度(ee%)は、ダイセル社製キラルカラムAD−Hにより決定した(n−ヘキサン/2−プロパノール=95/5 vol/vol,流量0.5mL/min,λ=254nm,τmaj=12.9min,τmin=25.0min)。
[α] 25=+40.5(c=0.49,MeOH),98%ee。
Using the same reaction apparatus as in Example 1, 1- (4-tert-butylphenyl) methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine 11a (25.8 mg) prepared in Reference Example 16 was used. , 0.10 mmol) and chiral phase transfer catalyst B (5.8 mg, 0.010 mmol), and the same operation as in Example 1 was performed except that the reaction was performed at −50 ° C. for 3 hours. 1- [2,2,2-trifluoro-1- (4-tert-butylphenyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine 11b (29.0 mg, 88%, 98 % Ee) was obtained as a white solid.
1 H NMR (CDCl 3 , 200 MHz) δ 1.30 (s, 9H), 1.32 (s, 3H), 1.47 (s, 3H), 1.64, 1.76 (ABquartet, J = 15. 9 Hz, 2H), 4.47 (q, J = 8.9 Hz, 1H), 7.38 (s, 5H).
13 C-NMR (CD 3 OD, 150.9 MHz) δ 24.9, 30.9, 32.7, 36.4, 44.9, 67.2 (q, J = 28.2 Hz), 67.4 127.5, 127.7 (q, J = 280.2 Hz), 130.4, 132.9, 154.6, 180.2.
19 F NMR (CDCl 3 , 188 MHz) δ-70.7 (d, J = 9.2 Hz, 3F).
IR (KBr) 3187, 3080, 2973, 1700, 1508, 1458, 1419, 1355, 1274, 1167, 1120, 1034, 900, 829, 667 cm −1 .
mp = 158.5-159.5 ° C. (dichloromethane / n-hexane recrystallized product).
MS (EI, m / z) 328 (M <+> ).
HRMS calcd. for C 17 H 23 F 3 N 2 O: 328.1762 Found: 328.1771.
The optical purity (ee%) was determined by a chiral column AD-H manufactured by Daicel (n-hexane / 2-propanol = 95/5 vol / vol, flow rate 0.5 mL / min, λ = 254 nm, τ maj = 12. 9 min , τ min = 25.0 min ).
[Α] D 25 = + 40.5 (c = 0.49, MeOH), 98% ee.

実施例12
(S)−1−[2,2,2−トリフルオロ−1−(3,4−ジメチルフェニル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジンの調製
Example 12
Preparation of (S) -1- [2,2,2-trifluoro-1- (3,4-dimethylphenyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine

実施例1と同じ反応装置を用い、参考例17で調製した1−(3,4−ジメチルフェニル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン13a(23.0mg,0.10mmol)、キラル相間移動触媒B(5.8mg,0.010mmol)を用い、−50℃で9時間反応を行った以外、実施例1と同じ操作を行い目的物の(S)−1−[2,2,2−トリフルオロ−1−(3,4−ジメチルフェニル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン13b(26.6mg,89%,88%ee)を白色固体として得た。
H−NMR(CDCl,200MHz)δ1.32(s,3H),1.47(s,3H),1.67,1.76(ABquartet,J=16.1Hz,2H),2.25(s,3H),2.26(s,3H),4.44(q,J=8.9Hz,1H),7.10−7.21(m,3H),7.55(br,1H)。
13C−NMR(CDOD,150.9MHz)δ20.5,20.8,24.9,30.9,45.0,67.4(q,J=28.2Hz),67.5,127.8(q,J=280.2Hz),130.7,130.8,131.7,134.3,139.0,140.0,180.3。
19F−NMR(CDCl,188MHz)δ−70.7(d,J=9.2Hz,3F)。
IR(KBr)3195,3081,2975,2928,1703,1507,1354,1278,1171,1119,852,812,785,730,652 cm−1
mp=175−177 oC(ジクロロメタン/n−ヘキサン再結晶品)。
MS(EI,m/z)300(M)。
HRMS calcd. for C1519O:300.1449 Found:300.1476。
光学純度(ee%)は、ダイセル社製キラルカラムAD−Hにより決定した(n−ヘキサン/2−プロパノール=95/5 vol/vol,流量1.0mL/min,λ=254nm,τmaj=7.4min,τmin=8.6min)。
[α] 25=+45.8(c=0.40,MeOH) ,88%ee。
Using the same reaction apparatus as in Example 1, 1- (3,4-dimethylphenyl) methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine 13a (23.0 mg) prepared in Reference Example 17 was used. , 0.10 mmol) and chiral phase transfer catalyst B (5.8 mg, 0.010 mmol), and the same operation as in Example 1 was performed except that the reaction was performed at −50 ° C. for 9 hours. 1- [2,2,2-trifluoro-1- (3,4-dimethylphenyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine 13b (26.6 mg, 89%, 88 % Ee) was obtained as a white solid.
1 H-NMR (CDCl 3 , 200 MHz) δ 1.32 (s, 3H), 1.47 (s, 3H), 1.67, 1.76 (ABquartet, J = 16.1 Hz, 2H), 2.25 (S, 3H), 2.26 (s, 3H), 4.44 (q, J = 8.9 Hz, 1H), 7.10-7.21 (m, 3H), 7.55 (br, 1H) ).
13 C-NMR (CD 3 OD, 150.9 MHz) δ 20.5, 20.8, 24.9, 30.9, 45.0, 67.4 (q, J = 28.2 Hz), 67.5, 127.8 (q, J = 280.2 Hz), 130.7, 130.8, 131.7, 134.3, 139.0, 140.0, 180.3.
19 F-NMR (CDCl 3 , 188 MHz) δ-70.7 (d, J = 9.2 Hz, 3F).
IR (KBr) 3195,3081,2975,2928,1703,1507,1354,1278,1171,1119,852,812,785,730,652 cm < -1 >.
mp = 175-177 oC (dichloromethane / n-hexane recrystallized product).
MS (EI, m / z) 300 (M <+> ).
HRMS calcd. for C 15 H 19 F 3 N 2 O: 300.1449 Found: 300.1476.
The optical purity (ee%) was determined by a chiral column AD-H manufactured by Daicel (n-hexane / 2-propanol = 95/5 vol / vol, flow rate 1.0 mL / min, λ = 254 nm, τ maj = 7. 4 min , τ min = 8.6 min ).
[Α] D 25 = + 45.8 (c = 0.40, MeOH), 88% ee.

実施例13
(S)−1−[2,2,2−トリフルオロ−1−(4−フルオロフェニル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジンの調製
Example 13
Preparation of (S) -1- [2,2,2-trifluoro-1- (4-fluorophenyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine

実施例1と同じ反応装置を用い、参考例18で調製した1−(4−フルオロフェニル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン12a(22.0mg,0.10mmol)、キラル相間移動触媒B(5.8mg,0.010mmol)を用い、−50℃で14時間反応を行った以外、実施例1と同じ操作を行い目的物(S)−1−[2,2,2−トリフルオロ−1−(4−フルオロフェニル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン12b(25.7mg,89%,89%ee)を白色固体として得た。
H−NMR(CDCl,200MHz)δ1.32(s,3H),1.47(s,3H),1.63,1.82(ABquartet,J=16.0Hz,2H),4.51(q,J=8.7Hz,1H),7.04−7.13(m,2H),7.44−7.51(m,3H)。
13C−NMR(CDOD,150.9MHz)δ25.1,30.8,45.0,66.7(q,J=28.2Hz),67.6,117.5(d,J=21.1Hz),127.6(q,J=279.7Hz),129.7(d,J=3.0Hz),135.2(d,J=7.5Hz),165.6(d,J=247.5Hz),180.2。
19F−NMR(CDCl,188MHz)δ −110.7(tt,J=5.3,7.9Hz,1F),−70.9(d,J=7.7Hz,3F)。
IR(KBr)3179,3082,2971,2842,1692,1606,1510,1422,1364,1273,1231,1174,1125,1038,901,832,738,646cm−1
mp=159−160℃(ジクロロメタン/n−ヘキサン再結晶品)。
MS(EI,m/z)290(M)。
HRMS calcd. for C1314O:290.1042 Found:290.1053。
光学純度(ee%)は、ダイセル社製キラルカラムOD−Hにより決定した(n−ヘキサン/2−プロパノール=95/5 vol/vol,流量0.5mL/min,λ=254nm,τmaj=15.8min,τmin=17.7min)。
[α] 25=+34.0(c=0.55,MeOH),89% ee。
Using the same reaction apparatus as in Example 1, 1- (4-fluorophenyl) methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine 12a (22.0 mg, 0) prepared in Reference Example 18 was used. .10 mmol) and chiral phase transfer catalyst B (5.8 mg, 0.010 mmol), and the same operation as in Example 1 was performed except that the reaction was performed at −50 ° C. for 14 hours. 2,2,2-trifluoro-1- (4-fluorophenyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine 12b (25.7 mg, 89%, 89% ee) on white Obtained as a solid.
1 H-NMR (CDCl 3 , 200 MHz) δ 1.32 (s, 3H), 1.47 (s, 3H), 1.63, 1.82 (ABquartet, J = 16.0 Hz, 2H), 4.51 (Q, J = 8.7 Hz, 1H), 7.04-7.13 (m, 2H), 7.44-7.51 (m, 3H).
13 C-NMR (CD 3 OD, 150.9 MHz) δ 25.1, 30.8, 45.0, 66.7 (q, J = 28.2 Hz), 67.6, 117.5 (d, J = 21.1 Hz), 127.6 (q, J = 279.7 Hz), 129.7 (d, J = 3.0 Hz), 135.2 (d, J = 7.5 Hz), 165.6 (d, J = 247.5 Hz), 180.2.
19 F-NMR (CDCl 3 , 188 MHz) δ-110.7 (tt, J = 5.3, 7.9 Hz, 1F), −70.9 (d, J = 7.7 Hz, 3F).
IR (KBr) 3179, 3082, 2971, 2842, 1692, 1606, 1510, 1422, 1364, 1273, 1231, 1174, 1125, 1038, 901, 832, 738, 646 cm −1 .
mp = 159-160 ° C. (dichloromethane / n-hexane recrystallized product).
MS (EI, m / z) 290 (M <+> ).
HRMS calcd. for C 13 H 14 F 4 N 2 O: 290.1042 Found: 290.1053.
The optical purity (ee%) was determined by a chiral column OD-H manufactured by Daicel (n-hexane / 2-propanol = 95/5 vol / vol, flow rate 0.5 mL / min, λ = 254 nm, τ maj = 15. 8 min, τ min = 17.7 min ).
[Α] D 25 = + 34.0 (c = 0.55, MeOH), 89% ee.

実施例14
(S)−1−[2,2,2−トリフルオロ−1−(4−クロロフェニル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジンの調製
Example 14
Preparation of (S) -1- [2,2,2-trifluoro-1- (4-chlorophenyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine

実施例1と同じ反応装置を用い、参考例19で調製した1−(4−クロロフェニル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン14a(23.7mg,0.10mmol)、キラル相間移動触媒B(5.8mg,0.010mmol)を用い、−50〜−40℃で9時間反応を行った以外、実施例1と同じ操作を行い目的物の(S)−1−[2,2,2−トリフルオロ−1−(4−クロロフェニル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン14b(24.9mg,81%,86%ee)を白色固体として得た。
H−NMR(CDCl,200MHz)δ1.32(s,3H),1.46(s,3H),1.66,1.83(ABquartet,J=16.2Hz,2H),4.49(q,J=8.7Hz,1H),7.34−7.45(m,4H),7.74(brs,1H)。
13C−NMR(CDOD,150.9MHz)δ25.1,30.8,45.0,66.8(q,J=28.7Hz),67.7,127.5(q,J=280.2Hz),130.8,132.4,134.7,137.6,180.2。
19F−NMR(CDCl,188MHz)δ−70.8(d,J=7.9Hz,3F)。
IR(KBr)3188,3080,2970,1692,1495,1272,1173,1126,1096,900,852,827,800,735,685,652cm−1
mp=202−204 ℃(ジクロロメタン/n−ヘキサン再結晶品)。
MS(EI,m/z)306(M)。
HRMS calcd. for C1314ClNO:306.6747 Found:306.0749。
光学純度(ee%)は、ダイセル社製キラルカラムOJ−Hにより決定した(n−ヘキサン/2−プロパノール=95/5 vol/vol,流量1.0 mL/min,λ=254nm,τmaj=9.5min,τmin=12.8min)。
[α] 25=+35.1(c=0.60,MeOH),86% ee。
Using the same reaction apparatus as in Example 1, 1- (4-chlorophenyl) methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine 14a (23.7 mg,. 10 mmol) and chiral phase transfer catalyst B (5.8 mg, 0.010 mmol), and the same operation as in Example 1 was performed except that the reaction was performed at −50 to −40 ° C. for 9 hours. 1- [2,2,2-trifluoro-1- (4-chlorophenyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine 14b (24.9 mg, 81%, 86% ee) Was obtained as a white solid.
1 H-NMR (CDCl 3 , 200 MHz) δ 1.32 (s, 3H), 1.46 (s, 3H), 1.66, 1.83 (ABquartet, J = 16.2 Hz, 2H), 4.49 (Q, J = 8.7 Hz, 1H), 7.34-7.45 (m, 4H), 7.74 (brs, 1H).
13 C-NMR (CD 3 OD, 150.9 MHz) δ 25.1, 30.8, 45.0, 66.8 (q, J = 28.7 Hz), 67.7, 127.5 (q, J = 280.2 Hz), 130.8, 132.4, 134.7, 137.6, 180.2.
19 F-NMR (CDCl 3 , 188 MHz) δ-70.8 (d, J = 7.9 Hz, 3F).
IR (KBr) 3188, 3080, 2970, 1692, 1495, 1272, 1173, 1126, 1096, 900, 852, 827, 800, 735, 685, 652 cm −1 .
mp = 202-204 ° C. (dichloromethane / n-hexane recrystallized product).
MS (EI, m / z) 306 (M <+> ).
HRMS calcd. for C 13 H 14 F 3 ClN 2 O: 306.6747 Found: 306.0749.
The optical purity (ee%) was determined by a chiral column OJ-H manufactured by Daicel (n-hexane / 2-propanol = 95/5 vol / vol, flow rate 1.0 mL / min, λ = 254 nm, τ maj = 9). .5 min , τ min = 12.8 min ).
[Α] D 25 = + 35.1 (c = 0.60, MeOH), 86% ee.

実施例15
(S)−1−[2,2,2−トリフルオロ−1−(4−ブロモフェニル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジンの調製
Example 15
Preparation of (S) -1- [2,2,2-trifluoro-1- (4-bromophenyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine

実施例1と同じ反応装置を用い、参考例20で調製した1−(4−ブロモフェニル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン15a(28.1mg,0.10mmol)、キラル相間移動触媒B(5.8mg,0.010mmol)を用い、−50〜−40℃で9時間反応を行った以外、実施例1と同じ操作を行い目的物の(S)−1−[2,2,2−トリフルオロ−1−(4−ブロモフェニル)−1−エチル]−5,5−ジメチル−3−オキソピラゾリジン15b(29.7mg,85%,83%ee)を白色固体として得た。
H−NMR(CDCl,200MHz)δ1.32(s,3H),1.46(s,3H),1.66,1.83(ABquartet,J=16.0Hz,2H),4.48(q,J=8.6Hz,1H),7.33−7.38(m,3H),7.49−7.56(m,2H)。
13C NMR(CDOD,150.9MHz)δ25.1,30.8,45.0,66.8(q,J=28.7Hz),67.7,125.7,127.5(q,J=280.2Hz),132.8,133.8,135.0,180.3。
19F−NMR(CDCl,188MHz)δ−70.8(d,J=9.2Hz,3F)。
IR(KBr)3200,3079,2970,1693,1595,1491,1417,1362,1269,1173,1126,1076,1012,900,824,733,652cm−1
mp=206−208℃(ジクロロメタン/n−ヘキサン再結晶品)。
MS (EI,m/z)350,352(M)。
HRMS calcd. for C1314BrNO:350.0242 Found:350.0233。
光学純度(ee%)は、ダイセル社製キラルカラムOJ−Hにより決定した(n−ヘキサン/2−プロパノール=95/5 vol/vol,流量0.5 mL/min,λ=254nm,τmaj=20.0min,τmin=26.6min)。
[α] 25=+33.5(c=0.82,MeOH),83% ee。
Using the same reaction apparatus as in Example 1, 1- (4-bromophenyl) methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine 15a (28.1 mg, 0) prepared in Reference Example 20 was used. .10 mmol) and chiral phase transfer catalyst B (5.8 mg, 0.010 mmol), and the same operation as in Example 1 was performed except that the reaction was performed at −50 to −40 ° C. for 9 hours. -1- [2,2,2-trifluoro-1- (4-bromophenyl) -1-ethyl] -5,5-dimethyl-3-oxopyrazolidine 15b (29.7 mg, 85%, 83% ee) was obtained as a white solid.
1 H-NMR (CDCl 3 , 200 MHz) δ 1.32 (s, 3H), 1.46 (s, 3H), 1.66, 1.83 (ABquartet, J = 16.0 Hz, 2H), 4.48 (Q, J = 8.6 Hz, 1H), 7.33-7.38 (m, 3H), 7.49-7.56 (m, 2H).
13 C NMR (CD 3 OD, 150.9 MHz) δ 25.1, 30.8, 45.0, 66.8 (q, J = 28.7 Hz), 67.7, 125.7, 127.5 (q , J = 280.2 Hz), 132.8, 133.8, 135.0, 180.3.
19 F-NMR (CDCl 3 , 188 MHz) δ-70.8 (d, J = 9.2 Hz, 3F).
IR (KBr) 3200, 3079, 2970, 1693, 1595, 1491, 1417, 1362, 1269, 1173, 1126, 1076, 1012, 900, 824, 733, 652 cm −1 .
mp = 206-208 ° C. (dichloromethane / n-hexane recrystallized product).
MS (EI, m / z) 350, 352 (M <+> ).
HRMS calcd. for C 13 H 14 F 3 BrN 2 O: 350.0242 Found: 350.0233.
The optical purity (ee%) was determined by a chiral column OJ-H manufactured by Daicel (n-hexane / 2-propanol = 95/5 vol / vol, flow rate 0.5 mL / min, λ = 254 nm, τ maj = 20). 0.0 min , τ min = 26.6 min ).
[Α] D 25 = + 33.5 (c = 0.82, MeOH), 83% ee.

実施例16
(S)−1−[1−(トリフルオロメチル)−1−(3−フェニル−2−プロピレニル)]−5,5−ジメチル−3−オキソピラゾリジンの調製
Example 16
Preparation of (S) -1- [1- (trifluoromethyl) -1- (3-phenyl-2-propylenyl)]-5,5-dimethyl-3-oxopyrazolidine

実施例1と同じ反応装置を用い、参考例21で調製した1−(3−フェニルプロピリデン−2−エン)−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン16a(22.8mg,0.10mmol)、キラル相間移動触媒B(5.8mg,0.010mmol)を用い、−50〜−40℃で9時間反応を行った以外、実施例1と同じ操作を行い目的物の(S)−1−[1−(トリフルオロメチル)−1−(3−フェニル−2−プロピレニル)]−5,5−ジメチル−3−オキソピラゾリジン16b(23.2mg,78%,79%ee)を白色固体として得た。
H−NMR(CDCl,200MHz)δ1.33(s,3H),1.42(s,3H),2.04,2.47(ABquartet,J=16.3Hz,2H),4.06(dq,J=8.5,8.5Hz,1H),6.41(dd,J=9.2,16.2Hz,1H),6.78(d,J=16.2Hz,1H),7.28−7.41(m,5H),7.66(brs,1H)。
13C−NMR(CDOD,150.9MHz)δ24.5,30.6,45.8,66.0(q,J=28.2Hz),67.0,119.9,127.5(q,J=279.7Hz),128.7,130.9,138.3,141.7,179.8。
19F NMR(CDCl,188MHz)δ−72.5(d,J=7.9Hz,3F)。
IR(KBr)3204,3081,2982,1687,1473,1362,1267,1173,1127,1086,1034,1007,977,903,750,684,649cm−1
mp=157−158.5℃(ジクロロメタン/n−ヘキサン再結晶品)。
MS(EI,m/z)298(M)。
HRMS calcd. for C1517O:298.1293 Found:298.1302。
光学純度(ee%)は、ダイセル社製キラルカラムOJ−Hにより決定した(n−ヘキサン/2−プロパノール=95/5 vol/vol,流量0.5 mL/min,λ=254nm,τmaj=30.6min,τmin=22.4min)。
[α] 25=+162.8(c=0.39,MeOH),79%ee。
Using the same reaction apparatus as in Example 1, 1- (3-phenylpropylidene-2-ene) -5,5-dimethyl-3-oxopyrazolidine N, N-betaine 16a (22. 8 mg, 0.10 mmol) and chiral phase transfer catalyst B (5.8 mg, 0.010 mmol), and the same operation as in Example 1 was performed except that the reaction was performed at −50 to −40 ° C. for 9 hours. (S) -1- [1- (Trifluoromethyl) -1- (3-phenyl-2-propylenyl)]-5,5-dimethyl-3-oxopyrazolidine 16b (23.2 mg, 78%, 79 % Ee) was obtained as a white solid.
1 H-NMR (CDCl 3 , 200 MHz) δ 1.33 (s, 3H), 1.42 (s, 3H), 2.04, 2.47 (ABquartet, J = 16.3 Hz, 2H), 4.06 (Dq, J = 8.5, 8.5 Hz, 1H), 6.41 (dd, J = 9.2, 16.2 Hz, 1H), 6.78 (d, J = 16.2 Hz, 1H), 7.28-7.41 (m, 5H), 7.66 (brs, 1H).
13 C-NMR (CD 3 OD, 150.9 MHz) δ 24.5, 30.6, 45.8, 66.0 (q, J = 28.2 Hz), 67.0, 119.9, 127.5 ( q, J = 279.7 Hz), 128.7, 130.9, 138.3, 141.7, 179.8.
19 F NMR (CDCl 3 , 188 MHz) δ-72.5 (d, J = 7.9 Hz, 3F).
IR (KBr) 3204,3081,2982,1687,1473,1362,1267,1173,1127,1086,1034,1007,977,903,750,684,649 cm < -1 >.
mp = 157-158.5 ° C. (dichloromethane / n-hexane recrystallized product).
MS (EI, m / z) 298 (M <+> ).
HRMS calcd. for C 15 H 17 F 3 N 2 O: 298.1293 Found: 298.1302.
The optical purity (ee%) was determined by a chiral column OJ-H manufactured by Daicel (n-hexane / 2-propanol = 95/5 vol / vol, flow rate 0.5 mL / min, λ = 254 nm, τ maj = 30). .6 min , τ min = 22.4 min ).
[Α] D 25 = + 162.8 (c = 0.39, MeOH), 79% ee.

実施例17
(S)−1−(2,2,2−トリフルオロ−1−シクロヘキシルエチル)−5,5−ジメチル−3−オキソピラゾリジンの調製
Example 17
Preparation of (S) -1- (2,2,2-trifluoro-1-cyclohexylethyl) -5,5-dimethyl-3-oxopyrazolidine

実施例1と同じ反応装置を用い、参考例22で調製した1−(シクロヘキシル)メチリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン17a(20.8mg,0.10mmol)、キラル相間移動触媒B(5.8mg,0.010mmol)を用い、−70〜−60℃で2時間反応を行った以外、実施例1と同じ操作を行い目的物の(S)−1−(2,2,2−トリフルオロ−1−シクロヘキシルエチル)−5,5−ジメチル−3−オキソピラゾリジン17b(23.7mg,85%,71%ee)を白色固体として得た。
H−NMR(CDCl,200MHz)δ1.14−1.25(m,5H),1.29(s,6H),1.64−1.91(m,6H),2.28,2.51(ABquartet,J =16.3Hz,2H),3.20(dq,J=4.1,9.0Hz,1H),7.68(brs,1H)。
13C−NMR(CDOD,150.9MHz)δ26.9,28.3,28.4,28.5,30.1,32.0,33.0,40.3,45.9,65.1,67.3(q,J=23.6Hz),128.3(q,J=287.2Hz),178.0。
19F−NMR(CDCl,188MHz)δ−66.1(d,J=9.2Hz,3F)。
IR(KBr)3155,3059,2930,2857,1689,1455,1350,1252,1157,1130,1102,1080,1047,771,702cm−1
mp=158.5−159.5 ℃(ジクロロメタン/n−ヘキサン再結晶品)。
MS(EI,m/z)278(M)。
HRMS calcd. for C1321O:278.1606 Found:278.1607。
光学純度(ee%)は、ダイセル社製キラルカラムAD−Hにより決定した(n−ヘキサン/2−プロパノール=98/2 vol/vol,流量0.5mL/min,λ= 254nm,τmaj=21.0min,τmin=25.1min)。
[α] 25 =−54.4 (c=0.43,MeOH),71%ee。
1- (cyclohexyl) methylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine 17a (20.8 mg, 0.10 mmol) prepared in Reference Example 22 using the same reaction apparatus as in Example 1 The same operation as in Example 1 was performed except that the reaction was performed at −70 to −60 ° C. for 2 hours using chiral phase transfer catalyst B (5.8 mg, 0.010 mmol). (2,2,2-trifluoro-1-cyclohexylethyl) -5,5-dimethyl-3-oxopyrazolidine 17b (23.7 mg, 85%, 71% ee) was obtained as a white solid.
1 H-NMR (CDCl 3 , 200 MHz) δ 1.14-1.25 (m, 5H), 1.29 (s, 6H), 1.64-1.91 (m, 6H), 2.28, 2 .51 (ABquartet, J = 16.3 Hz, 2H), 3.20 (dq, J = 4.1, 9.0 Hz, 1H), 7.68 (brs, 1H).
13 C-NMR (CD 3 OD, 150.9 MHz) δ 26.9, 28.3, 28.4, 28.5, 30.1, 32.0, 33.0, 40.3, 45.9, 65 1, 67.3 (q, J = 23.6 Hz), 128.3 (q, J = 287.2 Hz), 178.0.
19 F-NMR (CDCl 3 , 188 MHz) δ-66.1 (d, J = 9.2 Hz, 3F).
IR (KBr) 3155, 3059, 2930, 2857, 1689, 1455, 1350, 1252, 1157, 1130, 1102, 1080, 1047, 771, 702 cm −1 .
mp = 158.5-159.5 ° C. (dichloromethane / n-hexane recrystallized product).
MS (EI, m / z) 278 (M <+> ).
HRMS calcd. for C 13 H 21 F 3 N 2 O: 278.1606 Found: 278.1607.
The optical purity (ee%) was determined by a chiral column AD-H manufactured by Daicel (n-hexane / 2-propanol = 98/2 vol / vol, flow rate 0.5 mL / min, λ = 254 nm, τ maj = 21. 0 min, τ min = 25.1 min ).
[Α] D 25 = −54.4 (c = 0.43, MeOH), 71% ee.

実施例18
(S)−2,2,2−トリフルロロ−1−フェニルエチルアミンの調製
Example 18
Preparation of (S) -2,2,2-trifluoro-1-phenylethylamine

50 mLナスフラスコにスポンジニッケルを900mg,水を12.6mL加え,その後水酸化ナトリウムを1.7g加え,撹拌した。激しい発熱が落ち着いたら,ナスフラスコを70℃の湯浴で20分間撹拌した。室温に冷却後,水10 mLで3回,メタノ−ル6mLで5回洗浄した。封管に実施例1で調製した原料2a(90%ee,100 mg,0.367mmol)を加え,活性化したスポンジニッケルをメタノ−ル5mLを用いて50mLナスフラスコから移し,180℃に加熱し16時間撹拌した。室温に冷却後,セライトろ過し,ホットメタノ−ルで洗浄した。減圧下でメタノ−ルを留去し,シリカゲルカラムクロマトグラフィ−(n−ヘキサン:酢酸エチル=3:7)で単離精製し,中間体生成物18b(73.1 mg,73%)を白色固体として得た。
H−NMR(CDCl,200MHz)δ1.01(s,3H),1.17(s,3H),2.21,2.35(ABquartet,J=15.3Hz,2H),2.24(brs,1H),4.20(q,J=7.7Hz,1H),5.69(br,1H),7.10(br,1H),7.36(s,5H)。
13C−NMR(CDCl,150.9MHz)δ26.5,28.7,48.4,53.2,58.9(q,J=28.7Hz),125.5(q,J=280.7Hz),127.9,128.9,128.9,136.8,173.4。
19F−NMR(CDCl,188MHz)δ−74.1(d,J=7.9Hz,3F)。
IR(KBr)3360,3264,2967,1667,1457,1396,1267,1149,1119,882,762,703,633cm−1
mp=123−125℃(ジクロロメタン/n−ヘキサン再結晶品)。
MS(EI,m/z)274(M)。
HRMS calcd. for C1317O:274.1293Found:274.1283。
10mLナスフラスコに中間体18b(30mg,0.109mmol)、濃塩酸を2.5mL加え100℃において2日間加熱撹拌した。室温に冷却後、減圧下において濃塩酸を留去すると白色固体が得られた。ジエチルエ−テルを用いてろ過を行い、ジエチルエーテルで固体を洗浄した。フリ−ズドライを行い、水を除去することで目的とするα−トリフルオロメチルアミンの塩酸塩18c(22.7mg,98%)を得た。得られた目的物の光学純度は89%eeで誘導による光学純度の低下は認められなかった。
H−NMR(CDOD,600MHz)δ5.41(q,J=6.0Hz,1H),7.56−7.62(m,5H)。
13C−NMR(CDOD,150.9MHz)δ57.7(q,J=32.7Hz),125.8(q,J=280.2Hz),130.5,130.7,131.6,133.1。
19F−NMR(CDOD,188MHz)δ−72.5(d,J=7.9Hz,3F)。
光学純度(ee%)は、ダイセル社製キラルカラムOD−Hにより決定した(n−ヘキサン/2−プロパノール=95/5 vol/vol,流量0.5mL/min,λ=254nm,τmaj=22.8min,τmin=24.5min),89%ee。
To a 50 mL eggplant flask, 900 mg of sponge nickel and 12.6 mL of water were added, and then 1.7 g of sodium hydroxide was added and stirred. When the intense exotherm settled, the eggplant flask was stirred in a 70 ° C. water bath for 20 minutes. After cooling to room temperature, it was washed 3 times with 10 mL of water and 5 times with 6 mL of methanol. The raw material 2a prepared in Example 1 (90% ee, 100 mg, 0.367 mmol) was added to the sealed tube, and the activated sponge nickel was transferred from the 50 mL eggplant flask using 5 mL of methanol and heated to 180 ° C. Stir for 16 hours. After cooling to room temperature, the mixture was filtered through Celite and washed with hot methanol. The methanol was distilled off under reduced pressure, and the product was isolated and purified by silica gel column chromatography (n-hexane: ethyl acetate = 3: 7) to obtain the intermediate product 18b (73.1 mg, 73%) as a white solid. Got as.
1 H-NMR (CDCl 3 , 200 MHz) δ 1.01 (s, 3H), 1.17 (s, 3H), 2.21, 2.35 (ABquartet, J = 15.3 Hz, 2H), 2.24 (Brs, 1H), 4.20 (q, J = 7.7 Hz, 1H), 5.69 (br, 1H), 7.10 (br, 1H), 7.36 (s, 5H).
13 C-NMR (CDCl 3 , 150.9 MHz) δ 26.5, 28.7, 48.4, 53.2, 58.9 (q, J = 28.7 Hz), 125.5 (q, J = 280) .7 Hz), 127.9, 128.9, 128.9, 136.8, 173.4.
19 F-NMR (CDCl 3 , 188 MHz) δ-74.1 (d, J = 7.9 Hz, 3F).
IR (KBr) 3360, 3264, 2967, 1667, 1457, 1396, 1267, 1149, 1119, 882, 762, 703, 633 cm −1 .
mp = 123-125 ° C. (dichloromethane / n-hexane recrystallized product).
MS (EI, m / z) 274 (M <+> ).
HRMS calcd. for C 13 H 17 F 3 N 2 O: 274.1293Found: 274.1283.
Intermediate 18b (30 mg, 0.109 mmol) and 2.5 mL of concentrated hydrochloric acid were added to a 10 mL eggplant flask and heated and stirred at 100 ° C. for 2 days. After cooling to room temperature, concentrated hydrochloric acid was distilled off under reduced pressure to obtain a white solid. Filtration was performed using diethyl ether, and the solid was washed with diethyl ether. Freeze-drying was performed and water was removed to obtain the target α-trifluoromethylamine hydrochloride 18c (22.7 mg, 98%). The optical purity of the obtained target product was 89% ee, and no decrease in optical purity due to induction was observed.
1 H-NMR (CD 3 OD, 600 MHz) δ 5.41 (q, J = 6.0 Hz, 1H), 7.56-7.62 (m, 5H).
13 C-NMR (CD 3 OD, 150.9 MHz) δ 57.7 (q, J = 32.7 Hz), 125.8 (q, J = 280.2 Hz), 130.5, 130.7, 131.6 , 133.1.
19 F-NMR (CD 3 OD, 188 MHz) δ-72.5 (d, J = 7.9 Hz, 3F).
The optical purity (ee%) was determined by a chiral column OD-H manufactured by Daicel (n-hexane / 2-propanol = 95/5 vol / vol, flow rate 0.5 mL / min, λ = 254 nm, τ maj = 22. 8 min, τ min = 24.5 min ), 89% ee.

実施例19、20
実施例1で使用した1−ベンジリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタインに替えて、参考例5で調製した1−ベンジリデン−4,4−ジメチル−3−オキソピラゾリジン N,N−ベタインを用い表1中に示した条件下、反応を行った。結果を表1中に示した。
Examples 19 and 20
1-benzylidene-4,4-dimethyl-3-oxo prepared in Reference Example 5 instead of 1-benzylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine used in Example 1 Reaction was performed using pyrazolidine N, N-betaine under the conditions shown in Table 1. The results are shown in Table 1.

実施例21〜26
実施例1で使用した1−ベンジリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタインに替えて、参考例6で調製した1−ベンジリデン−3−オキソピラゾリジン N,N−ベタインを用い、水酸化カリウムムに替えて表2中に表示の塩基を用い、ジクロロメタン単独溶媒中で反応を行った。結果を表2中に示した。
Examples 21-26
1-benzylidene-3-oxopyrazolidine N, N prepared in Reference Example 6 instead of 1-benzylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine used in Example 1 -Betaine was used, and the reaction was carried out in dichloromethane alone using the bases shown in Table 2 instead of potassium hydroxide. The results are shown in Table 2.

実施例27〜39
実施例1で使用した1−ベンジリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタインに替えて、参考例6で調製した1−ベンジリデン−3−オキソピラゾリジン N,N−ベタインを用い、トリメチルシリルトリフルオロメタン(2.0モル)、表3中に示したキラル相間移動触媒(10mol%)、水酸化カリウム(0.2モル)、ジクロロメタン単独溶剤で室温下、反応を行った。結果を表3中に示した。
Examples 27-39
1-benzylidene-3-oxopyrazolidine N, N prepared in Reference Example 6 instead of 1-benzylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine used in Example 1 Using betaine, the reaction was carried out at room temperature with trimethylsilyl trifluoromethane (2.0 mol), chiral phase transfer catalyst (10 mol%) shown in Table 3, potassium hydroxide (0.2 mol), and dichloromethane alone. It was. The results are shown in Table 3.

実施例40〜47
実施例1と同じ反応装置を用い、参考例1で調製した1−ベンジリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタイン、キラル相間移動触媒A(10モル%)、トリメチルシリルトリフルオロメタン(10モル)、水酸化カリウム(6.0モル)を用い、表4中に示した溶剤に変更し反応を行った。結果を表4中に示した。
Examples 40-47
Using the same reactor as in Example 1, 1-benzylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine prepared in Reference Example 1, chiral phase transfer catalyst A (10 mol%), trimethylsilyl Using trifluoromethane (10 mol) and potassium hydroxide (6.0 mol), the reaction was carried out by changing to the solvents shown in Table 4. The results are shown in Table 4.

実施例48〜56
実施例1と同じ反応装置を用い、参考例1で調製した1−ベンジリデン−5,5−ジメチル−3−オキソピラゾリジン N,N−ベタインを用い、溶剤トルエン/ジクロロメタン=2/1で、表5中の示した条件下、−50℃で反応を行った。結果を表5中に示した。
Examples 48-56
Using the same reactor as in Example 1, 1-benzylidene-5,5-dimethyl-3-oxopyrazolidine N, N-betaine prepared in Reference Example 1 was used, and the solvent was toluene / dichloromethane = 2/1. The reaction was performed at −50 ° C. under the conditions shown in Table 5. The results are shown in Table 5.

実施例57
実施例15で調製した光学活性なトリフルオロメチル化物15bについて、X線結晶構造解析を行い、生成物の絶対配置が(S)体であることを確認した。
Example 57
The optically active trifluoromethylated product 15b prepared in Example 15 was subjected to X-ray crystal structure analysis, and it was confirmed that the absolute configuration of the product was the (S) isomer.

本発明の一般式(1)で表される3−オキソピラゾリジン N,N−ベタインのアニオン種受容体としての新規の用途が提案できた。アニオン種との反応により製造れる3−オキソピラゾリジン誘導体は、各種トリフルオロメチル基を含有するアミン類の合成原料として期待される有用な化合物である。   A novel use of 3-oxopyrazolidine N, N-betaine represented by the general formula (1) of the present invention as an anion species receptor could be proposed. A 3-oxopyrazolidine derivative produced by reaction with an anionic species is a useful compound expected as a raw material for the synthesis of amines containing various trifluoromethyl groups.

Claims (4)

下記一般式(1)
(式中、R及びRはそれぞれ独立に水素原子又は、炭素数1〜4のアルキル基を示し、Rは炭素数1〜10のアルキル基、置換基を有しても良いフェニル基、置換基を有しても良い1−ナフチル基、置換基を有しても良い2−ナフチル基、置換基を有しても良いアリールエチレニル基又は置換基を有しても良いアリールアルキルを示す)
で表される光学活性3−オキソピラゾリジン誘導体。
The following general formula (1)
(In the formula, R 1 and R 2 each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and R 3 is an alkyl group having 1 to 10 carbon atoms and an optionally substituted phenyl group. A 1-naphthyl group which may have a substituent, a 2-naphthyl group which may have a substituent, an arylethylenyl group which may have a substituent or an arylalkyl which may have a substituent Indicates)
An optically active 3-oxopyrazolidine derivative represented by the formula:
下記一般式(2)
(式中R、R及びRは前記に同じ)
で表される3−オキソピラゾリジン N,N−ベタイン誘導体とトリメチルシリルトリフルオロメタンをキラル相間移動触媒及び塩基の存在下、反応させることを特徴とする請求項1に記載された一般式(1)で表される光学活性3−オキソピラゾリジン誘導体の製造方法。
The following general formula (2)
(Wherein R 1 , R 2 and R 3 are the same as above)
The 3-oxopyrazolidine N, N-betaine derivative represented by the formula (3) is reacted with trimethylsilyltrifluoromethane in the presence of a chiral phase transfer catalyst and a base. The manufacturing method of the optically active 3-oxopyrazolidine derivative represented by these.
請求項2において、キラル相間移動触媒が下記一般式(3)
(式中Rは水素原子またはメトキシ基、Rは水素原子または4−メチルフェニルスルホニルメチル基、Rはエチル基またはエチレニル基、R及びRは各々独立して、水素原子、メチル基、エチル基、iso−プロピル基、tert−ブチル基、メトキシ基、エトキシ基、iso−プロポキシ基、tert−ブトキシ基、フェニル基、3,5−ビス(トリフルオロメチル)フェニル基、1−ナフチル基を示し、Xは塩素原子または臭素原子を示す)
で表されることを特徴とする請求項2に記載の製造方法。
The chiral phase transfer catalyst according to claim 2, wherein the chiral phase transfer catalyst has the following general formula (3):
Wherein R 4 is a hydrogen atom or a methoxy group, R 5 is a hydrogen atom or a 4-methylphenylsulfonylmethyl group, R 6 is an ethyl group or an ethylenyl group, R 7 and R 8 are each independently a hydrogen atom, methyl Group, ethyl group, iso-propyl group, tert-butyl group, methoxy group, ethoxy group, iso-propoxy group, tert-butoxy group, phenyl group, 3,5-bis (trifluoromethyl) phenyl group, 1-naphthyl A group, X represents a chlorine atom or a bromine atom)
It is represented by these, The manufacturing method of Claim 2 characterized by the above-mentioned.
請求項1に記載された一般式(1)で表される光学活性3−オキソピラゾリジン誘導体を還元触媒で開環した後、酸で処理することを特徴とする下記一般式(4)
(Rは前記に同じ)
で表される光学活性アミン類の製造方法。
The optically active 3-oxopyrazolidine derivative represented by the general formula (1) described in claim 1 is ring-opened with a reduction catalyst, and then treated with an acid, the following general formula (4)
(R 3 is the same as above)
The manufacturing method of optically active amines represented by these.
JP2009123457A 2009-05-21 2009-05-21 Optically active trifluoromethyl group-containing compound, process for producing the same, and process for producing trifluoromethyl group-containing optically active amines using the same Active JP5495618B2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP2009123457A JP5495618B2 (en) 2009-05-21 2009-05-21 Optically active trifluoromethyl group-containing compound, process for producing the same, and process for producing trifluoromethyl group-containing optically active amines using the same

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP2009123457A JP5495618B2 (en) 2009-05-21 2009-05-21 Optically active trifluoromethyl group-containing compound, process for producing the same, and process for producing trifluoromethyl group-containing optically active amines using the same

Publications (2)

Publication Number Publication Date
JP2010270065A true JP2010270065A (en) 2010-12-02
JP5495618B2 JP5495618B2 (en) 2014-05-21

Family

ID=43418407

Family Applications (1)

Application Number Title Priority Date Filing Date
JP2009123457A Active JP5495618B2 (en) 2009-05-21 2009-05-21 Optically active trifluoromethyl group-containing compound, process for producing the same, and process for producing trifluoromethyl group-containing optically active amines using the same

Country Status (1)

Country Link
JP (1) JP5495618B2 (en)

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5182272A (en) * 1974-12-11 1976-07-19 Agfa Gevaert Nv 44 monoharo 22 pirazorin 55 onkagobutsuno seizoho
JP2006521393A (en) * 2003-03-26 2006-09-21 イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー Preparation and use of 2-substituted-5-oxo-3-pyrazolidine carboxylates
JP2010270064A (en) * 2009-05-21 2010-12-02 Nagoya Institute Of Technology Manufacturing method for pyrazolidin-3-one derivative

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5182272A (en) * 1974-12-11 1976-07-19 Agfa Gevaert Nv 44 monoharo 22 pirazorin 55 onkagobutsuno seizoho
JP2006521393A (en) * 2003-03-26 2006-09-21 イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー Preparation and use of 2-substituted-5-oxo-3-pyrazolidine carboxylates
JP2010270064A (en) * 2009-05-21 2010-12-02 Nagoya Institute Of Technology Manufacturing method for pyrazolidin-3-one derivative

Non-Patent Citations (5)

* Cited by examiner, † Cited by third party
Title
JPN6013054604; Journal f. prakt. Chemie 318(2), 1976, pp253-260 *
JPN6013054606; Organic Letters 9(18), 2007, pp3707-3710 *
JPN6013054608; Angewandte Chemie International Edition 46, 2007, pp7667-7670 *
JPN6013054609; Angewandte Chemie International Edition 48, 2009, pp6324-6327 *
JPN6013054612; Tetrahedron 63, 2007, pp8521-8528 *

Also Published As

Publication number Publication date
JP5495618B2 (en) 2014-05-21

Similar Documents

Publication Publication Date Title
JPH0687800A (en) Phenylalkoxy derivative
JP6732744B2 (en) Method for producing biphenylamines from azobenzols by ruthenium catalysis
Tehrani et al. Electron transfer induced ring opening of 2-(bromomethyl) aziridines by magnesium in methanol
JP4384635B2 (en) Asymmetric urea compound and method for producing asymmetric compound by asymmetric conjugate addition reaction using the same
WO2014101690A1 (en) Method for preparing ezetimibe chiral intermediate
JPS6069072A (en) 1-(phenyl)-1-hydroxy-2-amino-3-fluoropropane derivative manufacturing intermediate
JP5495618B2 (en) Optically active trifluoromethyl group-containing compound, process for producing the same, and process for producing trifluoromethyl group-containing optically active amines using the same
KR101286617B1 (en) Method for preparing [1,2,3]-oxathiazolidine-2,2-dioxide or [1,2,5]-thiadiazolidine-1,1-dioxide derivatives
JP5170382B2 (en) Method for producing asymmetric catalytic aldol reaction product
CN102791661B (en) The manufacture method of difluoro cyclopropane compound
Shi et al. An efficient and green synthesis of 3, 3′‐benzylidenebis (4‐hydroxy‐6‐methylpyridin‐2 (1H)‐one) derivatives through multi‐component reaction in ionic liquid
JP2010270064A (en) Manufacturing method for pyrazolidin-3-one derivative
JP2005008633A (en) Method for producing fluorine-containing acetophenone and use of the same
JPH03161458A (en) Production of alpha,beta-unsaturated ketones
CN110437218B (en) Asymmetric preparation method of emtricitabine
JP6182183B2 (en) Method for producing duloxetine base and duloxetine hydrochloride
JP5870114B2 (en) Enantiomerically pure binaphthol derivative and method for producing the same (ENANTIOMERICALLY PURE BINAPHTOL DERIVATEIVES AND METHOD FOR PREPARING THE SAE)
KR101404616B1 (en) Method for Preparation of γ-fluorinated ketone derivatives
JP2003206282A (en) Method for producing oxazolidin-2-one derivative
JPH10120674A (en) Production of 2-methyl-3-(3,4-methylenedioxyphenyl) acrylic aldehyde
JP6764158B2 (en) Method for producing carbonyl compound
WO2002076958A1 (en) Process for producing 5-substituted oxazole compounds and 5-substituted imidazole compounds
JP4082883B2 (en) Method for producing aziridine derivative
JPH06211833A (en) Production of 1,3-dioxane-4,6-dione derivative
Sasaki et al. SUBSTITUENT EFFECTS IN REGIO-AND STEREOSELECTIVE RING-OPENING REACTION OF AZIRIDINES WITH Et3N· 3HF FOR β-FLUOROAMINE SYNTHESIS

Legal Events

Date Code Title Description
A621 Written request for application examination

Free format text: JAPANESE INTERMEDIATE CODE: A621

Effective date: 20120316

A521 Request for written amendment filed

Free format text: JAPANESE INTERMEDIATE CODE: A821

Effective date: 20120316

A131 Notification of reasons for refusal

Free format text: JAPANESE INTERMEDIATE CODE: A131

Effective date: 20131105

A521 Request for written amendment filed

Free format text: JAPANESE INTERMEDIATE CODE: A523

Effective date: 20131212

TRDD Decision of grant or rejection written
A01 Written decision to grant a patent or to grant a registration (utility model)

Free format text: JAPANESE INTERMEDIATE CODE: A01

Effective date: 20140225

A61 First payment of annual fees (during grant procedure)

Free format text: JAPANESE INTERMEDIATE CODE: A61

Effective date: 20140304

R150 Certificate of patent or registration of utility model

Ref document number: 5495618

Country of ref document: JP

Free format text: JAPANESE INTERMEDIATE CODE: R150

R250 Receipt of annual fees

Free format text: JAPANESE INTERMEDIATE CODE: R250

S111 Request for change of ownership or part of ownership

Free format text: JAPANESE INTERMEDIATE CODE: R313115

R350 Written notification of registration of transfer

Free format text: JAPANESE INTERMEDIATE CODE: R350

R250 Receipt of annual fees

Free format text: JAPANESE INTERMEDIATE CODE: R250

S531 Written request for registration of change of domicile

Free format text: JAPANESE INTERMEDIATE CODE: R313531

R350 Written notification of registration of transfer

Free format text: JAPANESE INTERMEDIATE CODE: R350

R250 Receipt of annual fees

Free format text: JAPANESE INTERMEDIATE CODE: R250

R250 Receipt of annual fees

Free format text: JAPANESE INTERMEDIATE CODE: R250

R250 Receipt of annual fees

Free format text: JAPANESE INTERMEDIATE CODE: R250

R250 Receipt of annual fees

Free format text: JAPANESE INTERMEDIATE CODE: R250

R250 Receipt of annual fees

Free format text: JAPANESE INTERMEDIATE CODE: R250

R250 Receipt of annual fees

Free format text: JAPANESE INTERMEDIATE CODE: R250